# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Jul 30 04:14:21 2022
#   Inital geometry file: a 105 line input string
#   Ligand name: 3-(2-chlorophenyl)-N-[(1R)-1-(3-methoxyphenyl)ethyl]propan-1-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cccc(c1)[C@@H](C)NCCCc2ccccc2Cl
#
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
 9IG  9IG  "3-(2-chlorophenyl)-N-[(1R)-1-(3-methoxyphenyl)ethyl]propan-1-amine"
  ligand  43  21  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_9IG
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
 9IG  C13   C   CH2   0  -0.436  222.4751  204.0636  183.3822
 9IG  C14   C   CH2   0  -0.508  222.3659  205.5872  183.3148
 9IG  C15   C   CR6   0   0.219  222.8690  206.2496  184.5640
 9IG  C16   C   CR16  0  -0.328  224.1849  206.7060  184.6316
 9IG  C17   C   CR16  0  -0.226  224.6991  207.2948  185.7761
 9IG  C18   C   CR16  0  -0.282  223.8935  207.4437  186.8962
 9IG  C19   C   CR16  0  -0.193  222.5809  206.9988  186.8632
 9IG  C20   C   CR6   0  -0.126  222.0891  206.4088  185.7076
 9IG  C01   C   CH3   0  -0.663  221.5370  199.7704  181.2965
 9IG  C02   C   CH1   0  -0.123  221.6480  201.2635  180.9976
 9IG  C03   C   CR6   0   0.140  222.6073  201.4807  179.8454
 9IG  C04   C   CR16  0  -0.447  222.1035  201.5242  178.5469
 9IG  C05   C   CR6   0   0.396  222.9620  201.6555  177.4583
 9IG  C06   C   CR16  0  -0.355  224.3379  201.7531  177.6744
 9IG  C07   C   CR16  0  -0.224  224.8308  201.7146  178.9665
 9IG  C08   C   CR16  0  -0.325  223.9769  201.5773  180.0549
 9IG  C12   C   CH2   0  -0.253  221.9546  203.4033  182.1160
 9IG  N11   N   NH1   0  -0.601  222.0883  201.9614  182.1899
 9IG  O09   O   O2    0  -0.470  222.5552  201.7018  176.1740
 9IG  CL21  CL  CL    0  -0.137  220.4381  205.8598  185.7125
 9IG  H1    H   HCH2  0   0.224  221.9165  203.6920  184.2468
 9IG  H2    H   HCH2  0   0.229  223.5188  203.7765  183.5356
 9IG  H3    H   HCH2  0   0.251  222.9491  205.9503  182.4652
 9IG  H4    H   HCH2  0   0.242  221.3293  205.8737  183.1234
 9IG  H5    H   HCR6  0   0.255  224.8151  206.5965  183.7568
 9IG  H6    H   HCR6  0   0.258  225.7248  207.6392  185.7920
 9IG  H7    H   HCR6  0   0.263  224.2797  207.9047  187.7956
 9IG  H8    H   HCR6  0   0.275  221.9429  207.1099  187.7297
 9IG  H10   H   HCH3  0   0.235  221.2060  199.2222  180.4150
 9IG  H11   H   HCH3  0   0.227  222.5009  199.3660  181.6083
 9IG  H12   H   HCH1  0   0.208  220.6540  201.6120  180.6693
 9IG  H13   H   HCR6  0   0.267  221.0314  201.4550  178.4080
 9IG  H14   H   HCR6  0   0.254  225.0066  201.8611  176.8294
 9IG  H15   H   HCR6  0   0.249  225.8989  201.7933  179.1271
 9IG  H16   H   HCR6  0   0.239  224.3710  201.5538  181.0620
 9IG  H17   H   HCH3  0   0.258  221.0732  201.6459  174.8141
 9IG  H18   H   HCH3  0   0.226  220.7583  200.6441  176.2411
 9IG  H19   H   HCH3  0   0.225  220.6004  202.4112  176.3399
 9IG  H20   H   HCH2  0   0.221  222.5351  203.7639  181.2615
 9IG  H21   H   HCH2  0   0.193  220.9144  203.7216  181.9376
 9IG  H22   H   HNH1  0   0.345  221.5529  201.6227  182.9810
 9IG  H9    H   HCH3  0   0.231  220.8138  199.5863  182.0937
 9IG  C10   C   CH3   0  -0.435  221.1753  201.5941  175.8955

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
 9IG  O09  C10   single    1.412  0.020  1.412
 9IG  O09  C05   single    1.348  0.020  1.348
 9IG  C05  C06   aromatic  1.396  0.020  1.396
 9IG  C05  C04   aromatic  1.393  0.020  1.393
 9IG  C06  C07   aromatic  1.384  0.020  1.384
 9IG  C04  C03   aromatic  1.393  0.020  1.393
 9IG  C07  C08   aromatic  1.390  0.020  1.390
 9IG  C03  C08   aromatic  1.389  0.020  1.389
 9IG  C03  C02   single    1.515  0.020  1.515
 9IG  C02  C01   single    1.527  0.020  1.527
 9IG  C02  N11   single    1.450  0.020  1.450
 9IG  N11  C12   single    1.450  0.020  1.450
 9IG  C12  C13   single    1.520  0.020  1.520
 9IG  C13  C14   single    1.529  0.020  1.529
 9IG  C16  C17   aromatic  1.386  0.020  1.386
 9IG  C16  C15   aromatic  1.394  0.020  1.394
 9IG  C17  C18   aromatic  1.388  0.020  1.388
 9IG  C14  C15   single    1.501  0.020  1.501
 9IG  C15  C20   aromatic  1.393  0.020  1.393
 9IG  C18  C19   aromatic  1.386  0.020  1.386
 9IG  C20  C19   aromatic  1.388  0.020  1.388
 9IG  C20  CL21  single    1.740  0.020  1.740
 9IG  C13  H1    single    0.970  0.020  1.090
 9IG  C13  H2    single    0.970  0.020  1.090
 9IG  C14  H3    single    0.970  0.020  1.090
 9IG  C14  H4    single    0.970  0.020  1.090
 9IG  C16  H5    single    0.930  0.020  1.080
 9IG  C17  H6    single    0.930  0.020  1.080
 9IG  C18  H7    single    0.930  0.020  1.080
 9IG  C19  H8    single    0.930  0.020  1.080
 9IG  C01  H9    single    0.970  0.020  1.090
 9IG  C01  H10   single    0.970  0.020  1.090
 9IG  C01  H11   single    0.970  0.020  1.090
 9IG  C02  H12   single    0.970  0.020  1.090
 9IG  C04  H13   single    0.930  0.020  1.080
 9IG  C06  H14   single    0.930  0.020  1.080
 9IG  C07  H15   single    0.930  0.020  1.080
 9IG  C08  H16   single    0.930  0.020  1.080
 9IG  C10  H17   single    0.970  0.020  1.090
 9IG  C10  H18   single    0.970  0.020  1.090
 9IG  C10  H19   single    0.970  0.020  1.090
 9IG  C12  H20   single    0.970  0.020  1.090
 9IG  C12  H21   single    0.970  0.020  1.090
 9IG  N11  H22   single    0.890  0.020  1.040

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
 9IG  H2    C13  H1   106.69  3.000
 9IG  H2    C13  C12  109.25  3.000
 9IG  H1    C13  C12  109.63  3.000
 9IG  H2    C13  C14  109.64  3.000
 9IG  H1    C13  C14  109.68  3.000
 9IG  C12   C13  C14  111.82  3.000
 9IG  H4    C14  H3   106.45  3.000
 9IG  H4    C14  C15  110.38  3.000
 9IG  H3    C14  C15  108.76  3.000
 9IG  H4    C14  C13  109.68  3.000
 9IG  H3    C14  C13  109.11  3.000
 9IG  C15   C14  C13  112.28  3.000
 9IG  C20   C15  C16  116.81  3.000
 9IG  C20   C15  C14  123.09  3.000
 9IG  C16   C15  C14  120.08  3.000
 9IG  H5    C16  C17  119.59  3.000
 9IG  H5    C16  C15  118.46  3.000
 9IG  C17   C16  C15  121.95  3.000
 9IG  H6    C17  C18  120.28  3.000
 9IG  H6    C17  C16  119.94  3.000
 9IG  C18   C17  C16  119.78  3.000
 9IG  H7    C18  C19  119.64  3.000
 9IG  H7    C18  C17  120.63  3.000
 9IG  C19   C18  C17  119.73  3.000
 9IG  H8    C19  C20  120.11  3.000
 9IG  H8    C19  C18  120.42  3.000
 9IG  C20   C19  C18  119.46  3.000
 9IG  CL21  C20  C19  117.91  3.000
 9IG  CL21  C20  C15  119.83  3.000
 9IG  C19   C20  C15  122.26  3.000
 9IG  H11   C01  H10  108.26  3.000
 9IG  H11   C01  H9   108.30  3.000
 9IG  H10   C01  H9   107.74  3.000
 9IG  H11   C01  C02  110.75  3.000
 9IG  H10   C01  C02  110.84  3.000
 9IG  H9    C01  C02  110.85  3.000
 9IG  H12   C02  N11  111.48  3.000
 9IG  H12   C02  C03  107.39  3.000
 9IG  N11   C02  C03  111.35  3.000
 9IG  H12   C02  C01  107.56  3.000
 9IG  N11   C02  C01  109.38  3.000
 9IG  C03   C02  C01  109.58  3.000
 9IG  C08   C03  C04  119.67  3.000
 9IG  C08   C03  C02  121.31  3.000
 9IG  C04   C03  C02  118.97  3.000
 9IG  H13   C04  C05  121.06  3.000
 9IG  H13   C04  C03  118.38  3.000
 9IG  C05   C04  C03  120.56  3.000
 9IG  O09   C05  C06  116.26  3.000
 9IG  C06   C05  C04  119.55  3.000
 9IG  O09   C05  C04  124.19  3.000
 9IG  H14   C06  C07  120.76  3.000
 9IG  H14   C06  C05  119.65  3.000
 9IG  C07   C06  C05  119.59  3.000
 9IG  H15   C07  C08  119.80  3.000
 9IG  H15   C07  C06  119.20  3.000
 9IG  C08   C07  C06  121.00  3.000
 9IG  H16   C08  C07  120.48  3.000
 9IG  H16   C08  C03  119.88  3.000
 9IG  C07   C08  C03  119.63  3.000
 9IG  H21   C12  H20  106.21  3.000
 9IG  H21   C12  N11  112.49  3.000
 9IG  H20   C12  N11  108.58  3.000
 9IG  H21   C12  C13  109.42  3.000
 9IG  H20   C12  C13  109.01  3.000
 9IG  N11   C12  C13  110.97  3.000
 9IG  H22   N11  C12  108.87  3.000
 9IG  H22   N11  C02  108.69  3.000
 9IG  C12   N11  C02  114.12  3.000
 9IG  C10   O09  C05  118.70  3.000
 9IG  H19   C10  H18  108.68  3.000
 9IG  H19   C10  H17  108.62  3.000
 9IG  H18   C10  H17  108.65  3.000
 9IG  H19   C10  O09  112.13  3.000
 9IG  H18   C10  O09  112.12  3.000
 9IG  H17   C10  O09  106.52  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
 9IG  CONST_01  C18   C17  C16  C15     0.00   0.0  0
 9IG  CONST_02  C18   C19  C20  C15     0.00   0.0  0
 9IG  CONST_03  C19   C18  C17  C16     0.00   0.0  0
 9IG  CONST_04  C19   C20  C15  C16     0.00   0.0  0
 9IG  CONST_05  C20   C15  C16  C17     0.00   0.0  0
 9IG  CONST_06  C20   C19  C18  C17     0.00   0.0  0
 9IG  CONST_07  C06   C05  C04  C03     0.00   0.0  0
 9IG  CONST_08  C06   C07  C08  C03     0.00   0.0  0
 9IG  CONST_09  C07   C06  C05  C04     0.00   0.0  0
 9IG  CONST_10  C07   C08  C03  C04     0.00   0.0  0
 9IG  CONST_11  C08   C07  C06  C05     0.00   0.0  0
 9IG  CONST_12  C08   C03  C04  C05     0.00   0.0  0
 9IG  CONST_13  C17   C16  C15  C14   180.00   0.0  0
 9IG  CONST_14  C19   C20  C15  C14   180.00   0.0  0
 9IG  CONST_15  CL21  C20  C15  C16   180.00   0.0  0
 9IG  CONST_16  CL21  C20  C19  C18   180.00   0.0  0
 9IG  CONST_17  C05   C04  C03  C02   180.00   0.0  0
 9IG  CONST_18  C07   C08  C03  C02   180.00   0.0  0
 9IG  CONST_19  O09   C05  C04  C03   180.00   0.0  0
 9IG  CONST_20  O09   C05  C06  C07   180.00   0.0  0
 9IG  CONST_21  H6    C17  C16  C15   180.00   0.0  0
 9IG  CONST_22  H8    C19  C20  C15   180.00   0.0  0
 9IG  CONST_23  H7    C18  C17  C16   180.00   0.0  0
 9IG  CONST_24  H8    C19  C18  C17   180.00   0.0  0
 9IG  CONST_25  H5    C16  C17  C18   180.00   0.0  0
 9IG  CONST_26  H6    C17  C18  C19   180.00   0.0  0
 9IG  CONST_27  H5    C16  C15  C20   180.00   0.0  0
 9IG  CONST_28  H7    C18  C19  C20   180.00   0.0  0
 9IG  CONST_29  H15   C07  C08  C03   180.00   0.0  0
 9IG  CONST_30  H14   C06  C05  C04   180.00   0.0  0
 9IG  CONST_31  H16   C08  C03  C04   180.00   0.0  0
 9IG  CONST_32  H15   C07  C06  C05   180.00   0.0  0
 9IG  CONST_33  H13   C04  C05  C06   180.00   0.0  0
 9IG  CONST_34  H16   C08  C07  C06   180.00   0.0  0
 9IG  CONST_35  H14   C06  C07  C08   180.00   0.0  0
 9IG  CONST_36  H13   C04  C03  C08   180.00   0.0  0
 9IG  Var_01    C16   C15  C14  C13    94.77  30.0  2
 9IG  Var_02    C20   C15  C14  C13   -83.38  30.0  2
 9IG  Var_03    C10   O09  C05  C04    -0.87  30.0  3
 9IG  Var_04    C10   O09  C05  C06   179.37  30.0  3
 9IG  Var_05    H3    C14  C15  C16   -26.08  30.0  2
 9IG  Var_06    H4    C14  C15  C16  -142.52  30.0  2
 9IG  Var_07    H3    C14  C15  C20   155.77  30.0  2
 9IG  Var_08    H4    C14  C15  C20    39.34  30.0  2
 9IG  Var_09    C12   C13  C14  C15   179.63  30.0  2
 9IG  Var_10    H1    C13  C14  C15    57.80  30.0  2
 9IG  Var_11    H2    C13  C14  C15   -59.04  30.0  2
 9IG  Var_12    H17   C10  O09  C05  -179.50  30.0  3
 9IG  Var_13    H18   C10  O09  C05   -60.78  30.0  3
 9IG  Var_14    H19   C10  O09  C05    61.81  30.0  3
 9IG  Var_15    C02   N11  C12  C13  -178.25  30.0  2
 9IG  Var_16    N11   C12  C13  C14   179.00  30.0  1
 9IG  Var_17    H22   N11  C12  C13    60.14  30.0  2
 9IG  Var_18    H20   C12  C13  C14    59.46  30.0  1
 9IG  Var_19    H21   C12  C13  C14   -56.29  30.0  1
 9IG  Var_20    H20   C12  N11  C02   -58.45  30.0  3
 9IG  Var_21    H21   C12  N11  C02    58.80  30.0  3
 9IG  Var_22    H3    C14  C13  C12   -59.72  30.0  3
 9IG  Var_23    H4    C14  C13  C12    56.53  30.0  3
 9IG  Var_24    H1    C13  C12  N11   -59.14  30.0  3
 9IG  Var_25    H2    C13  C12  N11    57.45  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
 9IG  chir_01  C02  C03  C01  N11  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
 9IG  plan-1  C14   0.020
 9IG  plan-1  C15   0.020
 9IG  plan-1  C16   0.020
 9IG  plan-1  C17   0.020
 9IG  plan-1  C18   0.020
 9IG  plan-1  C19   0.020
 9IG  plan-1  C20   0.020
 9IG  plan-1  CL21  0.020
 9IG  plan-1  H5    0.020
 9IG  plan-1  H6    0.020
 9IG  plan-1  H7    0.020
 9IG  plan-1  H8    0.020
 9IG  plan-2  C02   0.020
 9IG  plan-2  C03   0.020
 9IG  plan-2  C04   0.020
 9IG  plan-2  C05   0.020
 9IG  plan-2  C06   0.020
 9IG  plan-2  C07   0.020
 9IG  plan-2  C08   0.020
 9IG  plan-2  O09   0.020
 9IG  plan-2  H13   0.020
 9IG  plan-2  H14   0.020
 9IG  plan-2  H15   0.020
 9IG  plan-2  H16   0.020

