# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 13 02:03:18 2020
#   Inital geometry file: a 103 line input string
#   Ligand name: N-(cyclohexylmethyl)-4-oxo-4H-1-benzopyran-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O=C(NCC1CCCCC1)C2=CC(=O)c3ccccc3O2
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 9X0  9X0  N-(cyclohexylmethyl)-4-oxo-4H-1-benzopyran-2-carboxamide  ligand  40  21  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_9X0
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 9X0  C10  C  CR6   0   0.383  -2.4014   0.7974   0.1018
 9X0  C16  C  CH1   0  -0.302   3.5166  -0.1431   0.3150
 9X0  C15  C  CH2   0  -0.224   2.5883  -1.3341   0.1167
 9X0  C21  C  CH2   0  -0.416   4.9421  -0.6322   0.5676
 9X0  C20  C  CH2   0  -0.433   5.9138   0.5275   0.7582
 9X0  C19  C  CH2   0  -0.430   5.8735   1.4909  -0.4229
 9X0  C18  C  CH2   0  -0.431   4.4544   1.9853  -0.6798
 9X0  C17  C  CH2   0  -0.415   3.4852   0.8228  -0.8707
 9X0  N14  N  NH1   0  -0.660   1.2013  -0.9101   0.0761
 9X0  C01  C  C     0   0.550   0.2057  -1.7562  -0.1831
 9X0  O13  O  O     0  -0.471   0.3548  -2.9416  -0.4341
 9X0  C02  C  C     0   0.256  -1.1800  -1.1716  -0.1504
 9X0  O11  O  O2    0  -0.471  -1.2142   0.1483   0.0478
 9X0  C09  C  CR16  0  -0.326  -2.3572   2.1726   0.3071
 9X0  C08  C  CR16  0  -0.247  -3.5460   2.8694   0.3641
 9X0  C07  C  CR16  0  -0.242  -4.7706   2.2100   0.2207
 9X0  C06  C  CR16  0  -0.288  -4.7977   0.8482   0.0168
 9X0  C05  C  CR6   0  -0.128  -3.6069   0.1160  -0.0468
 9X0  C04  C  C     0   0.460  -3.6039  -1.3355  -0.2683
 9X0  O12  O  O     0  -0.427  -4.6275  -1.9866  -0.4094
 9X0  C03  C  C1    0  -0.467  -2.2783  -1.9270  -0.3069
 9X0  H1   H  HCH1  0   0.228   3.1852   0.3960   1.2129
 9X0  H2   H  HCH2  0   0.239   2.8388  -1.8475  -0.8154
 9X0  H3   H  HCH2  0   0.249   2.7274  -2.0537   0.9292
 9X0  H4   H  HCH2  0   0.231   4.9606  -1.2842   1.4453
 9X0  H5   H  HCH2  0   0.212   5.2689  -1.2441  -0.2812
 9X0  H6   H  HCH2  0   0.211   5.6565   1.0665   1.6763
 9X0  H7   H  HCH2  0   0.229   6.9263   0.1421   0.8999
 9X0  H8   H  HCH2  0   0.227   6.5443   2.3351  -0.2465
 9X0  H9   H  HCH2  0   0.209   6.2448   0.9799  -1.3177
 9X0  H10  H  HCH2  0   0.211   4.1242   2.5988   0.1654
 9X0  H11  H  HCH2  0   0.229   4.4308   2.6340  -1.5586
 9X0  H12  H  HCH2  0   0.212   3.7522   0.2734  -1.7810
 9X0  H13  H  HCH2  0   0.228   2.4754   1.2103  -1.0317
 9X0  H14  H  HNH1  0   0.412   0.9928   0.0428   0.3293
 9X0  H15  H  HCR6  0   0.288  -1.4058   2.6762   0.4184
 9X0  H16  H  HCR6  0   0.279  -3.5258   3.9394   0.5209
 9X0  H17  H  HCR6  0   0.272  -5.6933   2.7716   0.2698
 9X0  H18  H  HCR6  0   0.274  -5.7391   0.3281  -0.0987
 9X0  H19  H  H     0   0.291  -2.1722  -2.9912  -0.4611

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 9X0  C17  C18  single    1.526  0.020  1.526
 9X0  C17  C16  single    1.530  0.020  1.530
 9X0  C18  C19  single    1.525  0.020  1.525
 9X0  C19  C20  single    1.525  0.020  1.525
 9X0  C15  C16  single    1.523  0.020  1.523
 9X0  C15  N14  single    1.451  0.020  1.451
 9X0  C16  C21  single    1.528  0.020  1.528
 9X0  O13  C01  double    1.221  0.020  1.221
 9X0  C21  C20  single    1.525  0.020  1.525
 9X0  C01  N14  single    1.332  0.020  1.332
 9X0  C01  C02  single    1.504  0.020  1.504
 9X0  C02  C03  double    1.342  0.020  1.342
 9X0  C02  O11  single    1.335  0.020  1.335
 9X0  C03  C04  single    1.452  0.020  1.452
 9X0  O11  C10  single    1.354  0.020  1.354
 9X0  C04  O12  double    1.221  0.020  1.221
 9X0  C04  C05  single    1.468  0.020  1.468
 9X0  C10  C05  aromatic  1.393  0.020  1.393
 9X0  C10  C09  aromatic  1.391  0.020  1.391
 9X0  C05  C06  aromatic  1.399  0.020  1.399
 9X0  C09  C08  aromatic  1.379  0.020  1.379
 9X0  C06  C07  aromatic  1.377  0.020  1.377
 9X0  C08  C07  aromatic  1.398  0.020  1.398
 9X0  C16  H1   single    0.970  0.020  1.090
 9X0  C15  H2   single    0.970  0.020  1.090
 9X0  C15  H3   single    0.970  0.020  1.090
 9X0  C21  H4   single    0.970  0.020  1.090
 9X0  C21  H5   single    0.970  0.020  1.090
 9X0  C20  H6   single    0.970  0.020  1.090
 9X0  C20  H7   single    0.970  0.020  1.090
 9X0  C19  H8   single    0.970  0.020  1.090
 9X0  C19  H9   single    0.970  0.020  1.090
 9X0  C18  H10  single    0.970  0.020  1.090
 9X0  C18  H11  single    0.970  0.020  1.090
 9X0  C17  H12  single    0.970  0.020  1.090
 9X0  C17  H13  single    0.970  0.020  1.090
 9X0  N14  H14  single    0.860  0.020  1.020
 9X0  C09  H15  single    0.930  0.020  1.080
 9X0  C08  H16  single    0.930  0.020  1.080
 9X0  C07  H17  single    0.930  0.020  1.080
 9X0  C06  H18  single    0.930  0.020  1.080
 9X0  C03  H19  single    0.930  0.020  1.080

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 9X0  C05  C10  C09  121.80  3.000
 9X0  C09  C10  O11  116.86  3.000
 9X0  C05  C10  O11  121.34  3.000
 9X0  H1   C16  C17  108.51  3.000
 9X0  H1   C16  C21  107.66  3.000
 9X0  C17  C16  C21  110.45  3.000
 9X0  H1   C16  C15  107.83  3.000
 9X0  C21  C16  C15  109.87  3.000
 9X0  C17  C16  C15  112.36  3.000
 9X0  H3   C15  H2   107.17  3.000
 9X0  H3   C15  N14  109.54  3.000
 9X0  H2   C15  N14  109.42  3.000
 9X0  H3   C15  C16  109.88  3.000
 9X0  H2   C15  C16  109.79  3.000
 9X0  N14  C15  C16  110.96  3.000
 9X0  H5   C21  H4   106.47  3.000
 9X0  H5   C21  C20  109.35  3.000
 9X0  H4   C21  C20  110.02  3.000
 9X0  H5   C21  C16  109.19  3.000
 9X0  H4   C21  C16  109.84  3.000
 9X0  C20  C21  C16  111.83  3.000
 9X0  H7   C20  H6   106.42  3.000
 9X0  H7   C20  C19  110.36  3.000
 9X0  H6   C20  C19  109.40  3.000
 9X0  H7   C20  C21  109.79  3.000
 9X0  H6   C20  C21  109.23  3.000
 9X0  C19  C20  C21  111.52  3.000
 9X0  H9   C19  H8   106.51  3.000
 9X0  H9   C19  C18  109.22  3.000
 9X0  H8   C19  C18  110.37  3.000
 9X0  H9   C19  C20  109.22  3.000
 9X0  H8   C19  C20  110.30  3.000
 9X0  C18  C19  C20  111.10  3.000
 9X0  H11  C18  H10  106.36  3.000
 9X0  H11  C18  C17  109.76  3.000
 9X0  H10  C18  C17  109.38  3.000
 9X0  H11  C18  C19  110.38  3.000
 9X0  H10  C18  C19  109.40  3.000
 9X0  C17  C18  C19  111.43  3.000
 9X0  H13  C17  H12  106.28  3.000
 9X0  H13  C17  C18  109.58  3.000
 9X0  H12  C17  C18  109.33  3.000
 9X0  H13  C17  C16  110.91  3.000
 9X0  H12  C17  C16  108.79  3.000
 9X0  C18  C17  C16  111.79  3.000
 9X0  H14  N14  C01  119.66  3.000
 9X0  H14  N14  C15  117.84  3.000
 9X0  C01  N14  C15  122.30  3.000
 9X0  C02  C01  O13  119.62  3.000
 9X0  C02  C01  N14  115.94  3.000
 9X0  O13  C01  N14  124.44  3.000
 9X0  C03  C02  O11  123.56  3.000
 9X0  O11  C02  C01  114.27  3.000
 9X0  C03  C02  C01  122.17  3.000
 9X0  C02  O11  C10  120.15  3.000
 9X0  H15  C09  C08  121.23  3.000
 9X0  H15  C09  C10  120.21  3.000
 9X0  C08  C09  C10  118.56  3.000
 9X0  H16  C08  C07  119.86  3.000
 9X0  H16  C08  C09  119.32  3.000
 9X0  C07  C08  C09  120.83  3.000
 9X0  H17  C07  C06  120.23  3.000
 9X0  H17  C07  C08  119.85  3.000
 9X0  C06  C07  C08  119.92  3.000
 9X0  H18  C06  C05  118.96  3.000
 9X0  H18  C06  C07  120.55  3.000
 9X0  C05  C06  C07  120.49  3.000
 9X0  C04  C05  C06  121.72  3.000
 9X0  C06  C05  C10  118.41  3.000
 9X0  C04  C05  C10  119.87  3.000
 9X0  C03  C04  O12  123.01  3.000
 9X0  O12  C04  C05  122.87  3.000
 9X0  C03  C04  C05  114.11  3.000
 9X0  H19  C03  C04  119.64  3.000
 9X0  H19  C03  C02  119.38  3.000
 9X0  C04  C03  C02  120.97  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 9X0  CONST_01  C07  C06  C05  C10    0.00   0.0  0
 9X0  CONST_02  C07  C08  C09  C10    0.00   0.0  0
 9X0  CONST_03  C06  C05  C10  C09    0.00   0.0  0
 9X0  CONST_04  C06  C07  C08  C09    0.00   0.0  0
 9X0  CONST_05  C05  C10  C09  C08    0.00   0.0  0
 9X0  CONST_06  C05  C06  C07  C08    0.00   0.0  0
 9X0  CONST_07  H18  C06  C05  C10  180.00   0.0  0
 9X0  CONST_08  H16  C08  C09  C10  180.00   0.0  0
 9X0  CONST_09  H15  C09  C10  O11    0.00   0.0  0
 9X0  CONST_10  H17  C07  C08  C09  180.00   0.0  0
 9X0  CONST_11  C02  C01  N14  C15  180.00   0.0  0
 9X0  CONST_12  H14  N14  C01  C02    0.00   0.0  0
 9X0  CONST_13  O13  C01  N14  C15    0.00   0.0  0
 9X0  Var_01    C03  C02  O11  C10    0.08  30.0  1
 9X0  Var_02    C03  C04  C05  C10    0.11  30.0  1
 9X0  Var_03    C19  C18  C17  C16   55.46  30.0  1
 9X0  Var_04    C19  C20  C21  C16  -55.33  30.0  1
 9X0  Var_05    C18  C19  C20  C21   54.85  30.0  1
 9X0  Var_06    C17  C18  C19  C20  -54.91  30.0  1
 9X0  Var_07    C05  C04  C03  C02   -0.08  30.0  1
 9X0  Var_08    C05  C10  O11  C02   -0.05  30.0  1
 9X0  Var_09    C04  C03  C02  O11   -0.01  30.0  1
 9X0  Var_10    C01  N14  C15  C16  175.12  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 9X0  chir_01  C16  C17  C15  C21  negativ

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 9X0  plan-1  C15  0.020
 9X0  plan-1  N14  0.020
 9X0  plan-1  C01  0.020
 9X0  plan-1  O13  0.020
 9X0  plan-1  C02  0.020
 9X0  plan-1  H14  0.020
 9X0  plan-2  C10  0.020
 9X0  plan-2  O11  0.020
 9X0  plan-2  C09  0.020
 9X0  plan-2  C08  0.020
 9X0  plan-2  C07  0.020
 9X0  plan-2  C06  0.020
 9X0  plan-2  C05  0.020
 9X0  plan-2  C04  0.020
 9X0  plan-2  H15  0.020
 9X0  plan-2  H16  0.020
 9X0  plan-2  H17  0.020
 9X0  plan-2  H18  0.020
 9X0  plan-3  C05  0.020
 9X0  plan-3  C04  0.020
 9X0  plan-3  O12  0.020
 9X0  plan-3  C03  0.020

