##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal #
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Phenyltetrahydropyrimido[4,5-c]pyridazine 2'-deoxyribonucleoside
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H18 N4 O4, H2 O'
_chemical_formula_sum     'C17 H20 N4 O5'
_chemical_formula_iupac     'C17 H18 N4 O4, H2 O'
_chemical_formula_weight     360.37
_chemical_melting_point     ?
_chemical_absolute_configuration     syn
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     7.2057(3)
_cell_length_b     11.0792(4)
_cell_length_c     41.2346(16)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3291.9(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9843
_cell_measurement_theta_min     2.70
_cell_measurement_theta_max     24.51
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.19
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.454
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1520
_exptl_absorpt_coefficient_mu     0.109
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_absorpt_correction_T_min     0.9793
_exptl_absorpt_correction_T_max     0.9906
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     91832
_diffrn_reflns_av_R_equivalents     0.1182
_diffrn_reflns_av_sigmaI/netI     0.0500
_diffrn_reflns_theta_min     2.87
_diffrn_reflns_theta_max     28.00
_diffrn_reflns_theta_full     28.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -54
_diffrn_reflns_limit_l_max     54
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     4528
_reflns_number_gt     3773
_reflns_threshold_expression     >I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0630
_refine_ls_R_factor_gt     0.0453
_refine_ls_wR_factor_gt     0.0893
_refine_ls_wR_factor_ref     0.0962
_refine_ls_goodness_of_fit_ref     1.072
_refine_ls_restrained_S_all     1.072
_refine_ls_number_reflns     4528
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0414P)²+1.1870P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.267
_refine_diff_density_min     -0.314
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                          'Established by known chemical absolute configuration'
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXTL (Sheldrick, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2020)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C11C 0.1273(3) 0.1164(2) 0.86156(6) 0.0122(5) Uani d . 1 1 . .
    C C12C 0.1019(4) 0.0262(2) 0.88477(6) 0.0168(6) Uani d . 1 1 . .
    H H12C 0.1304 0.0424 0.9068 0.020 Uiso calc R 1 1 . .
    C C13C 0.0357(4) -0.0868(3) 0.87604(7) 0.0226(7) Uani d . 1 1 . .
    H H13C 0.0180 -0.1469 0.8922 0.027 Uiso calc R 1 1 . .
    C C14C -0.0046(4) -0.1126(3) 0.84406(7) 0.0210(6) Uani d . 1 1 . .
    H H14C -0.0495 -0.1901 0.8381 0.025 Uiso calc R 1 1 . .
    C C15C 0.0209(4) -0.0242(3) 0.82060(6) 0.0167(6) Uani d . 1 1 . .
    H H15C -0.0057 -0.0416 0.7985 0.020 Uiso calc R 1 1 . .
    C C16C 0.0849(4) 0.0891(2) 0.82921(6) 0.0147(6) Uani d . 1 1 . .
    H H16C 0.1004 0.1491 0.8130 0.018 Uiso calc R 1 1 . .
    N N11 0.3292(3) 0.41735(19) 0.85314(5) 0.0112(4) Uani d . 1 1 . .
    N N12 0.2625(3) 0.30591(19) 0.84694(5) 0.0119(5) Uani d . 1 1 . .
    C C13 0.1985(3) 0.2372(2) 0.87082(6) 0.0111(5) Uani d . 1 1 . .
    C C14 0.2023(3) 0.2773(2) 0.90351(6) 0.0110(5) Uani d . 1 1 . .
    H H14 0.1567 0.2274 0.9205 0.013 Uiso calc R 1 1 . .
    C C14A 0.2721(3) 0.3878(2) 0.90999(6) 0.0104(5) Uani d . 1 1 . .
    C C15 0.2906(4) 0.4370(2) 0.94371(6) 0.0120(5) Uani d . 1 1 . .
    H H15E 0.1740 0.4215 0.9557 0.014 Uiso calc R 1 1 . .
    H H15D 0.3919 0.3937 0.9550 0.014 Uiso calc R 1 1 . .
    N N16 0.3298(3) 0.56673(19) 0.94420(5) 0.0117(5) Uani d . 1 1 . .
    C C17 0.4030(4) 0.6273(2) 0.91836(6) 0.0110(5) Uani d . 1 1 . .
    O O17 0.4677(3) 0.73036(16) 0.92069(4) 0.0149(4) Uani d . 1 1 . .
    N N18 0.3986(3) 0.5716(2) 0.88878(5) 0.0125(5) Uani d . 1 1 . .
    H H18N 0.4416 0.6117 0.8720 0.019 Uiso calc R 1 1 . .
    C C18A 0.3315(3) 0.4570(2) 0.88350(6) 0.0097(5) Uani d . 1 1 . .
    C C11' 0.3522(4) 0.6207(2) 0.97618(6) 0.0124(5) Uani d . 1 1 . .
    H H11' 0.3774 0.7089 0.9736 0.015 Uiso calc R 1 1 . .
    C C12' 0.1876(4) 0.6044(2) 0.99892(6) 0.0126(5) Uani d . 1 1 . .
    H H12A 0.1022 0.6743 0.9977 0.015 Uiso calc R 1 1 . .
    H H12B 0.1179 0.5298 0.9937 0.015 Uiso calc R 1 1 . .
    C C13' 0.2784(4) 0.5957(2) 1.03218(6) 0.0124(5) Uani d . 1 1 . .
    H H13' 0.2013 0.5469 1.0475 0.015 Uiso calc R 1 1 . .
    O O13' 0.3197(3) 0.71160(17) 1.04531(5) 0.0203(4) Uani d . 1 1 . .
    H H13O 0.2239 0.7405 1.0539 0.030 Uiso calc R 1 1 . .
    C C14' 0.4620(4) 0.5328(2) 1.02456(6) 0.0124(5) Uani d . 1 1 . .
    H H14' 0.5604 0.5632 1.0396 0.015 Uiso calc R 1 1 . .
    O O14' 0.5082(2) 0.56537(17) 0.99174(4) 0.0144(4) Uani d . 1 1 . .
    C C15' 0.4451(4) 0.3977(2) 1.02795(6) 0.0146(6) Uani d . 1 1 . .
    H H15A 0.4125 0.3778 1.0506 0.018 Uiso calc R 1 1 . .
    H H15B 0.3434 0.3686 1.0138 0.018 Uiso calc R 1 1 . .
    O O15' 0.6133(3) 0.33672(18) 1.01940(5) 0.0187(4) Uani d . 1 1 . .
    H H15O 0.5917 0.2868 1.0045 0.028 Uiso calc R 1 1 . .
    O O100 0.4971(3) 0.17289(17) 0.97409(4) 0.0181(4) Uani d . 1 1 . .
    H H101 0.3678 0.1520 0.9737 0.027 Uiso d R 1 1 . .
    H H100 0.5383 0.1635 0.9521 0.027 Uiso d R 1 1 . .
    C C21C 0.7560(4) 0.3512(2) 0.89090(6) 0.0114(5) Uani d . 1 1 . .
    C C22C 0.8280(4) 0.4273(2) 0.86712(6) 0.0142(5) Uani d . 1 1 . .
    H H22C 0.8285 0.4018 0.8451 0.017 Uiso calc R 1 1 . .
    C C23C 0.8992(4) 0.5400(2) 0.87517(6) 0.0159(6) Uani d . 1 1 . .
    H H23C 0.9485 0.5908 0.8587 0.019 Uiso calc R 1 1 . .
    C C24C 0.8984(4) 0.5781(2) 0.90713(6) 0.0162(6) Uani d . 1 1 . .
    H H24C 0.9470 0.6551 0.9127 0.019 Uiso calc R 1 1 . .
    C C25C 0.8264(4) 0.5037(2) 0.93095(6) 0.0150(6) Uani d . 1 1 . .
    H H25C 0.8245 0.5302 0.9529 0.018 Uiso calc R 1 1 . .
    C C26C 0.7569(4) 0.3909(2) 0.92312(6) 0.0133(5) Uani d . 1 1 . .
    H H26C 0.7097 0.3401 0.9397 0.016 Uiso calc R 1 1 . .
    N N21 0.5765(3) 0.0444(2) 0.90156(5) 0.0140(5) Uani d . 1 1 . .
    N N22 0.6355(3) 0.1576(2) 0.90698(5) 0.0137(5) Uani d . 1 1 . .
    C C23 0.6818(3) 0.2301(2) 0.88234(6) 0.0108(5) Uani d . 1 1 . .
    C C24 0.6575(4) 0.1919(2) 0.85004(6) 0.0119(5) Uani d . 1 1 . .
    H H24 0.6846 0.2449 0.8326 0.014 Uiso calc R 1 1 . .
    C C24A 0.5947(4) 0.0782(2) 0.84413(6) 0.0110(5) Uani d . 1 1 . .
    C C25 0.5540(4) 0.0311(2) 0.81091(6) 0.0123(5) Uani d . 1 1 . .
    H H25D 0.4524 0.0791 0.8012 0.015 Uiso calc R 1 1 . .
    H H25E 0.6654 0.0415 0.7971 0.015 Uiso calc R 1 1 . .
    N N26 0.5008(3) -0.09635(19) 0.81099(5) 0.0121(4) Uani d . 1 1 . .
    C C27 0.4895(4) -0.1679(2) 0.83793(6) 0.0126(5) Uani d . 1 1 . .
    O O27 0.4581(3) -0.27703(16) 0.83627(4) 0.0177(4) Uani d . 1 1 . .
    N N28 0.5126(3) -0.1135(2) 0.86718(5) 0.0149(5) Uani d . 1 1 . .
    H H28N 0.4941 -0.1572 0.8847 0.022 Uiso calc R 1 1 . .
    C C28A 0.5630(4) 0.0056(2) 0.87133(6) 0.0116(5) Uani d . 1 1 . .
    C C21' 0.4844(4) -0.1552(2) 0.77978(6) 0.0139(6) Uani d . 1 1 . .
    H H21' 0.4342 -0.2385 0.7830 0.017 Uiso calc R 1 1 . .
    C C22' 0.3656(4) -0.0891(3) 0.75456(6) 0.0146(6) Uani d . 1 1 . .
    H H22A 0.2774 -0.1454 0.7441 0.017 Uiso calc R 1 1 . .
    H H22B 0.2945 -0.0228 0.7648 0.017 Uiso calc R 1 1 . .
    C C23' 0.5029(4) -0.0395(2) 0.72989(6) 0.0118(5) Uani d . 1 1 . .
    H H23' 0.5416 0.0441 0.7360 0.014 Uiso calc R 1 1 . .
    O O23' 0.4186(3) -0.03919(18) 0.69867(4) 0.0156(4) Uani d . 1 1 . .
    H H23O 0.5010 -0.0327 0.6844 0.023 Uiso calc R 1 1 . .
    O O24' 0.6678(3) -0.16308(17) 0.76598(4) 0.0159(4) Uani d . 1 1 . .
    C C24' 0.6665(4) -0.1255(2) 0.73252(6) 0.0140(6) Uani d . 1 1 . .
    H H24' 0.6434 -0.1973 0.7184 0.017 Uiso calc R 1 1 . .
    C C25' 0.8534(4) -0.0731(3) 0.72456(6) 0.0197(6) Uani d . 1 1 . .
    H H25A 0.9512 -0.1338 0.7289 0.024 Uiso calc R 1 1 . .
    H H25B 0.8583 -0.0516 0.7013 0.024 Uiso calc R 1 1 . .
    O O25' 0.8859(3) 0.0315(2) 0.74372(4) 0.0268(5) Uani d . 1 1 . .
    H H25O 0.9598 0.0776 0.7340 0.040 Uiso calc R 1 1 . .
    O O200 0.1440(3) 0.14220(17) 0.70583(5) 0.0198(4) Uani d . 1 1 . .
    H H201 0.2028 0.2117 0.7152 0.030 Uiso d R 1 1 . .
    H H200 0.2437 0.0873 0.7012 0.030 Uiso d R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C11C C12C . 1.396(4) ?
    C11C C16C . 1.401(4) ?
    C11C C13 . 1.483(4) y
    C12C C13C . 1.387(4) ?
    C12C H12C . 0.9500 ?
    C13C C14C . 1.380(4) ?
    C13C H13C . 0.9500 ?
    C14C C15C . 1.389(4) ?
    C14C H14C . 0.9500 ?
    C15C C16C . 1.383(4) ?
    C15C H15C . 0.9500 ?
    C16C H16C . 0.9500 ?
    N11 C18A . 1.327(3) ?
    N11 N12 . 1.349(3) ?
    N12 C13 . 1.328(3) ?
    C13 C14 . 1.419(3) ?
    C14 C14A . 1.351(4) ?
    C14 H14 . 0.9500 ?
    C14A C18A . 1.401(3) ?
    C14A C15 . 1.499(3) ?
    C15 N16 . 1.465(3) ?
    C15 H15E . 0.9900 ?
    C15 H15D . 0.9900 ?
    N16 C17 . 1.365(3) ?
    N16 C11' . 1.457(3) y
    C17 O17 . 1.237(3) ?
    C17 N18 . 1.368(3) ?
    N18 C18A . 1.375(3) ?
    N18 H18N . 0.8800 ?
    C11' O14' . 1.432(3) ?
    C11' C12' . 1.523(3) ?
    C11' H11' . 1.0000 ?
    C12' C13' . 1.522(3) ?
    C12' H12A . 0.9900 ?
    C12' H12B . 0.9900 ?
    C13' O13' . 1.425(3) ?
    C13' C14' . 1.528(4) ?
    C13' H13' . 1.0000 ?
    O13' H13O . 0.8400 ?
    C14' O14' . 1.440(3) ?
    C14' C15' . 1.508(4) ?
    C14' H14' . 1.0000 ?
    C15' O15' . 1.431(3) ?
    C15' H15A . 0.9900 ?
    C15' H15B . 0.9900 ?
    O15' H15O . 0.8400 ?
    O100 H101 . 0.9600 ?
    O100 H100 . 0.9602 ?
    C21C C22C . 1.393(4) ?
    C21C C26C . 1.400(3) ?
    C21C C23 . 1.486(4) y
    C22C C23C . 1.391(4) ?
    C22C H22C . 0.9500 ?
    C23C C24C . 1.384(4) ?
    C23C H23C . 0.9500 ?
    C24C C25C . 1.383(4) ?
    C24C H24C . 0.9500 ?
    C25C C26C . 1.384(4) ?
    C25C H25C . 0.9500 ?
    C26C H26C . 0.9500 ?
    N21 C28A . 1.322(3) ?
    N21 N22 . 1.344(3) ?
    N22 C23 . 1.337(3) ?
    C23 C24 . 1.409(3) ?
    C24 C24A . 1.360(4) ?
    C24 H24 . 0.9500 ?
    C24A C28A . 1.399(3) ?
    C24A C25 . 1.495(3) ?
    C25 N26 . 1.463(3) ?
    C25 H25D . 0.9900 ?
    C25 H25E . 0.9900 ?
    N26 C27 . 1.367(3) ?
    N26 C21' . 1.448(3) y
    C27 O27 . 1.232(3) ?
    C27 N28 . 1.358(3) ?
    N28 C28A . 1.379(3) ?
    N28 H28N . 0.8800 ?
    C21' O24' . 1.441(3) ?
    C21' C22' . 1.533(4) ?
    C21' H21' . 1.0000 ?
    C22' C23' . 1.522(3) ?
    C22' H22A . 0.9900 ?
    C22' H22B . 0.9900 ?
    C23' O23' . 1.423(3) ?
    C23' C24' . 1.519(4) ?
    C23' H23' . 1.0000 ?
    O23' H23O . 0.8400 ?
    O24' C24' . 1.441(3) ?
    C24' C25' . 1.503(4) ?
    C24' H24' . 1.0000 ?
    C25' O25' . 1.422(3) ?
    C25' H25A . 0.9900 ?
    C25' H25B . 0.9900 ?
    O25' H25O . 0.8400 ?
    O200 H201 . 0.9600 ?
    O200 H200 . 0.9601 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C12C C11C C16C . . 118.0(2) ?
    C12C C11C C13 . . 121.0(2) ?
    C16C C11C C13 . . 121.0(2) ?
    C13C C12C C11C . . 120.9(2) ?
    C13C C12C H12C . . 119.6 ?
    C11C C12C H12C . . 119.6 ?
    C14C C13C C12C . . 120.5(3) ?
    C14C C13C H13C . . 119.8 ?
    C12C C13C H13C . . 119.8 ?
    C13C C14C C15C . . 119.5(3) ?
    C13C C14C H14C . . 120.3 ?
    C15C C14C H14C . . 120.3 ?
    C16C C15C C14C . . 120.3(2) ?
    C16C C15C H15C . . 119.8 ?
    C14C C15C H15C . . 119.8 ?
    C15C C16C C11C . . 120.8(2) ?
    C15C C16C H16C . . 119.6 ?
    C11C C16C H16C . . 119.6 ?
    C18A N11 N12 . . 119.1(2) ?
    C13 N12 N11 . . 120.5(2) ?
    N12 C13 C14 . . 121.2(2) ?
    N12 C13 C11C . . 116.5(2) ?
    C14 C13 C11C . . 122.2(2) ?
    C14A C14 C13 . . 118.6(2) ?
    C14A C14 H14 . . 120.7 ?
    C13 C14 H14 . . 120.7 ?
    C14 C14A C18A . . 117.1(2) ?
    C14 C14A C15 . . 123.1(2) ?
    C18A C14A C15 . . 119.8(2) ?
    N16 C15 C14A . . 112.7(2) y
    N16 C15 H15E . . 109.1 ?
    C14A C15 H15E . . 109.1 ?
    N16 C15 H15D . . 109.1 ?
    C14A C15 H15D . . 109.1 ?
    H15E C15 H15D . . 107.8 ?
    C17 N16 C11' . . 117.5(2) ?
    C17 N16 C15 . . 123.1(2) ?
    C11' N16 C15 . . 115.87(19) ?
    O17 C17 N16 . . 122.6(2) ?
    O17 C17 N18 . . 119.7(2) ?
    N16 C17 N18 . . 117.7(2) ?
    C17 N18 C18A . . 124.5(2) ?
    C17 N18 H18N . . 117.8 ?
    C18A N18 H18N . . 117.8 ?
    N11 C18A N18 . . 117.3(2) ?
    N11 C18A C14A . . 123.4(2) ?
    N18 C18A C14A . . 119.3(2) ?
    O14' C11' N16 . . 108.5(2) ?
    O14' C11' C12' . . 106.55(19) ?
    N16 C11' C12' . . 115.0(2) ?
    O14' C11' H11' . . 108.9 ?
    N16 C11' H11' . . 108.9 ?
    C12' C11' H11' . . 108.9 ?
    C13' C12' C11' . . 103.2(2) ?
    C13' C12' H12A . . 111.1 ?
    C11' C12' H12A . . 111.1 ?
    C13' C12' H12B . . 111.1 ?
    C11' C12' H12B . . 111.1 ?
    H12A C12' H12B . . 109.1 ?
    O13' C13' C12' . . 112.0(2) ?
    O13' C13' C14' . . 108.0(2) ?
    C12' C13' C14' . . 102.44(19) ?
    O13' C13' H13' . . 111.3 ?
    C12' C13' H13' . . 111.3 ?
    C14' C13' H13' . . 111.3 ?
    C13' O13' H13O . . 109.5 ?
    O14' C14' C15' . . 110.8(2) ?
    O14' C14' C13' . . 106.2(2) ?
    C15' C14' C13' . . 111.3(2) ?
    O14' C14' H14' . . 109.5 ?
    C15' C14' H14' . . 109.5 ?
    C13' C14' H14' . . 109.5 ?
    C11' O14' C14' . . 110.27(18) ?
    O15' C15' C14' . . 112.2(2) ?
    O15' C15' H15A . . 109.2 ?
    C14' C15' H15A . . 109.2 ?
    O15' C15' H15B . . 109.2 ?
    C14' C15' H15B . . 109.2 ?
    H15A C15' H15B . . 107.9 ?
    C15' O15' H15O . . 109.5 ?
    H101 O100 H100 . . 105.0 ?
    C22C C21C C26C . . 118.4(2) ?
    C22C C21C C23 . . 120.8(2) ?
    C26C C21C C23 . . 120.7(2) ?
    C23C C22C C21C . . 120.9(2) ?
    C23C C22C H22C . . 119.6 ?
    C21C C22C H22C . . 119.6 ?
    C24C C23C C22C . . 120.0(2) ?
    C24C C23C H23C . . 120.0 ?
    C22C C23C H23C . . 120.0 ?
    C25C C24C C23C . . 119.7(2) ?
    C25C C24C H24C . . 120.1 ?
    C23C C24C H24C . . 120.1 ?
    C24C C25C C26C . . 120.6(2) ?
    C24C C25C H25C . . 119.7 ?
    C26C C25C H25C . . 119.7 ?
    C25C C26C C21C . . 120.5(2) ?
    C25C C26C H26C . . 119.8 ?
    C21C C26C H26C . . 119.8 ?
    C28A N21 N22 . . 118.9(2) ?
    C23 N22 N21 . . 120.9(2) ?
    N22 C23 C24 . . 120.4(2) ?
    N22 C23 C21C . . 116.8(2) ?
    C24 C23 C21C . . 122.7(2) ?
    C24A C24 C23 . . 119.3(2) ?
    C24A C24 H24 . . 120.4 ?
    C23 C24 H24 . . 120.4 ?
    C24 C24A C28A . . 116.3(2) ?
    C24 C24A C25 . . 123.6(2) ?
    C28A C24A C25 . . 120.1(2) ?
    N26 C25 C24A . . 112.8(2) y
    N26 C25 H25D . . 109.0 ?
    C24A C25 H25D . . 109.0 ?
    N26 C25 H25E . . 109.0 ?
    C24A C25 H25E . . 109.0 ?
    H25D C25 H25E . . 107.8 ?
    C27 N26 C21' . . 117.2(2) ?
    C27 N26 C25 . . 125.2(2) ?
    C21' N26 C25 . . 117.0(2) ?
    O27 C27 N28 . . 120.5(2) ?
    O27 C27 N26 . . 122.3(2) ?
    N28 C27 N26 . . 117.2(2) ?
    C27 N28 C28A . . 124.5(2) ?
    C27 N28 H28N . . 117.7 ?
    C28A N28 H28N . . 117.7 ?
    N21 C28A N28 . . 116.6(2) ?
    N21 C28A C24A . . 123.8(2) ?
    N28 C28A C24A . . 119.6(2) ?
    O24' C21' N26 . . 107.7(2) ?
    O24' C21' C22' . . 105.87(19) ?
    N26 C21' C22' . . 115.7(2) ?
    O24' C21' H21' . . 109.1 ?
    N26 C21' H21' . . 109.1 ?
    C22' C21' H21' . . 109.1 ?
    C23' C22' C21' . . 105.2(2) ?
    C23' C22' H22A . . 110.7 ?
    C21' C22' H22A . . 110.7 ?
    C23' C22' H22B . . 110.7 ?
    C21' C22' H22B . . 110.7 ?
    H22A C22' H22B . . 108.8 ?
    O23' C23' C24' . . 113.4(2) ?
    O23' C23' C22' . . 109.1(2) ?
    C24' C23' C22' . . 103.3(2) ?
    O23' C23' H23' . . 110.3 ?
    C24' C23' H23' . . 110.3 ?
    C22' C23' H23' . . 110.3 ?
    C23' O23' H23O . . 109.5 ?
    C24' O24' C21' . . 110.73(18) ?
    O24' C24' C25' . . 108.3(2) ?
    O24' C24' C23' . . 104.78(19) ?
    C25' C24' C23' . . 115.9(2) ?
    O24' C24' H24' . . 109.2 ?
    C25' C24' H24' . . 109.2 ?
    C23' C24' H24' . . 109.2 ?
    O25' C25' C24' . . 109.9(2) ?
    O25' C25' H25A . . 109.7 ?
    C24' C25' H25A . . 109.7 ?
    O25' C25' H25B . . 109.7 ?
    C24' C25' H25B . . 109.7 ?
    H25A C25' H25B . . 108.2 ?
    C25' O25' H25O . . 109.5 ?
    H201 O200 H200 . . 105.0 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C16C C11C C12C C13C . . . . -0.4(4) ?
    C13 C11C C12C C13C . . . . -179.8(3) ?
    C11C C12C C13C C14C . . . . 0.7(5) ?
    C12C C13C C14C C15C . . . . -0.2(5) ?
    C13C C14C C15C C16C . . . . -0.5(4) ?
    C14C C15C C16C C11C . . . . 0.8(4) ?
    C12C C11C C16C C15C . . . . -0.4(4) ?
    C13 C11C C16C C15C . . . . 179.1(2) ?
    C18A N11 N12 C13 . . . . 0.6(3) ?
    N11 N12 C13 C14 . . . . -1.5(4) ?
    N11 N12 C13 C11C . . . . 179.7(2) ?
    C12C C11C C13 N12 . . . . 163.4(2) ?
    C16C C11C C13 N12 . . . . -16.1(4) y
    C12C C11C C13 C14 . . . . -15.4(4) ?
    C16C C11C C13 C14 . . . . 165.1(2) ?
    N12 C13 C14 C14A . . . . 0.2(4) ?
    C11C C13 C14 C14A . . . . 179.0(2) ?
    C13 C14 C14A C18A . . . . 1.8(4) ?
    C13 C14 C14A C15 . . . . -177.2(2) ?
    C14 C14A C15 N16 . . . . -167.1(2) ?
    C18A C14A C15 N16 . . . . 13.9(3) ?
    C14A C15 N16 C17 . . . . -20.9(3) ?
    C14A C15 N16 C11' . . . . -179.2(2) ?
    C11' N16 C17 O17 . . . . -8.2(4) ?
    C15 N16 C17 O17 . . . . -166.1(2) ?
    C11' N16 C17 N18 . . . . 173.7(2) ?
    C15 N16 C17 N18 . . . . 15.7(4) ?
    O17 C17 N18 C18A . . . . 179.4(2) ?
    N16 C17 N18 C18A . . . . -2.4(4) ?
    N12 N11 C18A N18 . . . . -179.3(2) ?
    N12 N11 C18A C14A . . . . 1.6(4) ?
    C17 N18 C18A N11 . . . . 177.2(2) ?
    C17 N18 C18A C14A . . . . -3.7(4) ?
    C14 C14A C18A N11 . . . . -2.8(4) ?
    C15 C14A C18A N11 . . . . 176.2(2) ?
    C14 C14A C18A N18 . . . . 178.1(2) ?
    C15 C14A C18A N18 . . . . -2.9(4) ?
    C17 N16 C11' O14' . . . . -97.5(3) y
    C15 N16 C11' O14' . . . . 62.0(3) ?
    C17 N16 C11' C12' . . . . 143.3(2) ?
    C15 N16 C11' C12' . . . . -57.1(3) ?
    O14' C11' C12' C13' . . . . 26.9(3) ?
    N16 C11' C12' C13' . . . . 147.1(2) ?
    C11' C12' C13' O13' . . . . 82.3(2) ?
    C11' C12' C13' C14' . . . . -33.2(3) ?
    O13' C13' C14' O14' . . . . -89.8(2) ?
    C12' C13' C14' O14' . . . . 28.6(2) ?
    O13' C13' C14' C15' . . . . 149.5(2) ?
    C12' C13' C14' C15' . . . . -92.1(2) ?
    N16 C11' O14' C14' . . . . -133.5(2) ?
    C12' C11' O14' C14' . . . . -9.2(3) ?
    C15' C14' O14' C11' . . . . 108.6(2) ?
    C13' C14' O14' C11' . . . . -12.4(3) ?
    O14' C14' C15' O15' . . . . 59.2(3) ?
    C13' C14' C15' O15' . . . . 177.20(19) y
    C26C C21C C22C C23C . . . . 0.0(4) ?
    C23 C21C C22C C23C . . . . -179.3(2) ?
    C21C C22C C23C C24C . . . . -0.3(4) ?
    C22C C23C C24C C25C . . . . 0.0(4) ?
    C23C C24C C25C C26C . . . . 0.7(4) ?
    C24C C25C C26C C21C . . . . -1.0(4) ?
    C22C C21C C26C C25C . . . . 0.6(4) ?
    C23 C21C C26C C25C . . . . 179.9(2) ?
    C28A N21 N22 C23 . . . . -0.6(4) ?
    N21 N22 C23 C24 . . . . 4.4(4) ?
    N21 N22 C23 C21C . . . . -176.5(2) ?
    C22C C21C C23 N22 . . . . 172.4(2) ?
    C26C C21C C23 N22 . . . . -6.8(4) y
    C22C C21C C23 C24 . . . . -8.5(4) ?
    C26C C21C C23 C24 . . . . 172.2(2) ?
    N22 C23 C24 C24A . . . . -3.2(4) ?
    C21C C23 C24 C24A . . . . 177.8(2) ?
    C23 C24 C24A C28A . . . . -1.6(4) ?
    C23 C24 C24A C25 . . . . 176.5(2) ?
    C24 C24A C25 N26 . . . . 176.0(2) ?
    C28A C24A C25 N26 . . . . -6.1(3) ?
    C24A C25 N26 C27 . . . . -0.6(4) ?
    C24A C25 N26 C21' . . . . -171.4(2) ?
    C21' N26 C27 O27 . . . . -3.3(4) ?
    C25 N26 C27 O27 . . . . -174.1(3) ?
    C21' N26 C27 N28 . . . . 177.3(2) ?
    C25 N26 C27 N28 . . . . 6.5(4) ?
    O27 C27 N28 C28A . . . . 174.4(3) ?
    N26 C27 N28 C28A . . . . -6.2(4) ?
    N22 N21 C28A N28 . . . . 176.2(2) ?
    N22 N21 C28A C24A . . . . -4.5(4) ?
    C27 N28 C28A N21 . . . . 179.0(2) ?
    C27 N28 C28A C24A . . . . -0.3(4) ?
    C24 C24A C28A N21 . . . . 5.5(4) ?
    C25 C24A C28A N21 . . . . -172.6(2) ?
    C24 C24A C28A N28 . . . . -175.2(2) ?
    C25 C24A C28A N28 . . . . 6.7(4) ?
    C27 N26 C21' O24' . . . . -103.8(3) y
    C25 N26 C21' O24' . . . . 67.8(3) ?
    C27 N26 C21' C22' . . . . 138.1(2) ?
    C25 N26 C21' C22' . . . . -50.3(3) ?
    O24' C21' C22' C23' . . . . -11.4(3) ?
    N26 C21' C22' C23' . . . . 107.7(2) ?
    C21' C22' C23' O23' . . . . 147.3(2) ?
    C21' C22' C23' C24' . . . . 26.3(3) ?
    N26 C21' O24' C24' . . . . -133.6(2) ?
    C22' C21' O24' C24' . . . . -9.2(3) ?
    C21' O24' C24' C25' . . . . 150.6(2) ?
    C21' O24' C24' C23' . . . . 26.2(3) ?
    O23' C23' C24' O24' . . . . -149.9(2) ?
    C22' C23' C24' O24' . . . . -31.9(2) ?
    O23' C23' C24' C25' . . . . 90.7(3) ?
    C22' C23' C24' C25' . . . . -151.3(2) ?
    O24' C24' C25' O25' . . . . -63.0(3) ?
    C23' C24' C25' O25' . . . . 54.4(3) y
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N18 H18N O27 1_565 0.88 1.92 2.773(3) 161.6
    O13' H13O O17 4_467 0.84 2.15 2.968(3) 166.0
    O15' H15O O100 . 0.84 1.91 2.736(2) 169.3
    O100 H101 O15' 4_457 0.96 1.86 2.781(3) 159.7
    O100 H100 N22 . 0.96 1.99 2.946(3) 175.0
    N28 H28N O17 1_545 0.88 1.95 2.823(3) 173.2
    O23' H23O N11 3_646 0.84 2.05 2.846(3) 158.3
    O25' H25O O200 1_655 0.84 1.90 2.721(3) 164.3
    O200 H201 O24' 3_656 0.96 1.84 2.801(3) 175.2
    O200 H200 O23' . 0.96 1.89 2.836(3) 168.8
data_global
_journal_date_recd_electronic     2022-04-13
_journal_date_accepted     2022-06-02
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2022
_journal_volume     78
_journal_issue      7
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229622005964
_journal_coeditor_code     CU3182
_publ_contact_author_name     'Frank Seela'
_publ_contact_author_address
;
Laboratory of Bioorganic Chemistry and Chemical Biology
Center for Nanotechnology
Heisenbergstrasse 11
48149 Münster
Germany
Laboratorium für Organische und Bioorganische Chemie
Institut für Chemie neuer Materialien
Universität Osnabrück
Barbarastrasse 7
49069 Osnabrück
Germany
;
_publ_contact_author_email     frank.seela@uni-osnabrueck.de
_publ_section_title
;
The 2'-deoxyribofuranoside of
3-phenyltetrahydropyrimido[4,5-c]pyridazin-7-one: a bicyclic nucleoside
with sugar residues in N and S conformations, and its molecular
recognition
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hui Mei' .
;
Laboratory of Bioorganic Chemistry and Chemical Biology
Center for Nanotechnology
Heisenbergstrasse 11
48149 Münster
Germany
;
    'Simone Budow-Busse' .
;
Laboratory of Bioorganic Chemistry and Chemical Biology
Center for Nanotechnology
Heisenbergstrasse 11
48149 Münster
Germany
;
    'Dasharath Kondhare' .
;
Laboratory of Bioorganic Chemistry and Chemical Biology
Center for Nanotechnology
Heisenbergstrasse 11
48149 Münster
Germany
;
    'Henning Eickmeier' .
;
Anorganische Chemie II
Institut für Chemie neuer Materialien
Universitt Osnabrück
Barbarastrasse 7
49069 Osnabrück
Germany
;
    'Hans Reuter' .
;
Anorganische Chemie II
Institut für Chemie neuer Materialien
Universitt Osnabrück
Barbarastrasse 7
49069 Osnabrück
Germany
;
    'Frank Seela' .
;
Laboratory of Bioorganic Chemistry and Chemical Biology
Center for Nanotechnology
Heisenbergstrasse 11
48149 Münster
Germany
Laboratorium für Organische und Bioorganische Chemie
Institut für Chemie neuer Materialien
Universität Osnabrück
Barbarastrasse 7
49069 Osnabrück
Germany
;
_publ_section_synopsis
;
3-Phenyltetrahydropyrimido[4,5-c]pyridazine 2'-deoxyribonucleoside shows
two conformations in the crystalline state with distinct differences observed
for the sugar moiety (N versus S sugar pucker). The nucleoside mimics
the recognition face of dT and forms stable base pairs with dA.
;
