# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 25 02:56:53 2020
#   Inital geometry file: a 61 line input string
#   Ligand name: 5-bromanyl-1-methyl-indole-2-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cn1c(cc2cc(Br)ccc12)C(O)=O
#
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
 R2N  R2N  '5-bromanyl-1-methyl-indole-2-carboxylic acid'  ligand  22  14  .  2021-08-23  2021-08-23  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_R2N
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
 R2N  C1    C   CH3   0  -0.526  -2.9450  -2.1430  -0.0349
 R2N  N2    N   NR5   0  -0.577  -2.1951  -0.9023  -0.0199
 R2N  C3    C   CR5   0   0.206  -2.6829   0.3897  -0.0173
 R2N  C4    C   CR15  0  -0.377  -1.6419   1.2825  -0.0012
 R2N  C5    C   CR56  0   0.066  -0.4494   0.5242   0.0064
 R2N  C6    C   CR16  0  -0.303   0.9076   0.8772   0.0230
 R2N  C7    C   CR6   0  -0.129   1.8309  -0.1391   0.0262
 R2N  BR8   BR  BR    0  -0.059   3.6764   0.2796   0.0486
 R2N  C9    C   CR16  0  -0.239   1.4529  -1.4950   0.0132
 R2N  C10   C   CR16  0  -0.304   0.1244  -1.8545  -0.0033
 R2N  C11   C   CR56  0   0.371  -0.8336  -0.8347  -0.0061
 R2N  C12   C   C     0   0.514  -4.0899   0.8129  -0.0296
 R2N  O13   O   O     0  -0.436  -4.4058   1.9792  -0.0223
 R2N  O14   O   OH1   0  -0.591  -4.9627  -0.1810  -0.0493
 R2N  H1    H   HCH3  0   0.261  -3.5834  -2.2279   0.8407
 R2N  H1A   H   HCH3  0   0.261  -3.5518  -2.2258  -0.9331
 R2N  H1B   H   HCH3  0   0.264  -2.2460  -2.9725  -0.0227
 R2N  H4    H   HCR5  0   0.269  -1.7331   2.3565   0.0044
 R2N  H6    H   HCR6  0   0.276   1.2016   1.9187   0.0325
 R2N  H9    H   HCR6  0   0.280   2.2077  -2.2692   0.0160
 R2N  H10   H   HCR6  0   0.280  -0.1412  -2.9027  -0.0139
 R2N  HO14  H   HOH1  0   0.493  -5.8659   0.1718  -0.0547

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
 R2N  H1   C1    single    0.970  0.020  1.090
 R2N  H1B  C1    single    0.970  0.020  1.090
 R2N  N2   C1    single    1.450  0.020  1.450
 R2N  C1   H1A   single    0.970  0.020  1.090
 R2N  C11  N2    aromatic  1.363  0.020  1.363
 R2N  N2   C3    aromatic  1.381  0.020  1.381
 R2N  C4   C3    aromatic  1.372  0.020  1.372
 R2N  C3   C12   single    1.469  0.020  1.469
 R2N  C5   C4    aromatic  1.413  0.020  1.413
 R2N  C4   H4    single    0.930  0.020  1.080
 R2N  C6   C5    aromatic  1.402  0.020  1.402
 R2N  C11  C5    aromatic  1.412  0.020  1.412
 R2N  C7   C6    aromatic  1.373  0.020  1.373
 R2N  C6   H6    single    0.930  0.020  1.080
 R2N  BR8  C7    single    1.892  0.020  1.892
 R2N  C9   C7    aromatic  1.408  0.020  1.408
 R2N  H9   C9    single    0.930  0.020  1.080
 R2N  C9   C10   aromatic  1.376  0.020  1.376
 R2N  H10  C10   single    0.930  0.020  1.080
 R2N  C10  C11   aromatic  1.399  0.020  1.399
 R2N  O13  C12   double    1.208  0.020  1.208
 R2N  C12  O14   single    1.323  0.020  1.323
 R2N  O14  HO14  single    0.850  0.020  0.980

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
 R2N  H1B   C1   H1A  108.10  3.000
 R2N  H1A   C1   H1   109.38  3.000
 R2N  H1B   C1   H1   108.04  3.000
 R2N  H1A   C1   N2   111.25  3.000
 R2N  H1B   C1   N2   108.72  3.000
 R2N  H1    C1   N2   111.24  3.000
 R2N  C11   N2   C3   107.84  3.000
 R2N  C3    N2   C1   128.17  3.000
 R2N  C11   N2   C1   123.99  3.000
 R2N  C12   C3   C4   122.65  3.000
 R2N  C12   C3   N2   127.42  3.000
 R2N  C4    C3   N2   109.93  3.000
 R2N  H4    C4   C5   127.30  3.000
 R2N  H4    C4   C3   125.76  3.000
 R2N  C5    C4   C3   106.93  3.000
 R2N  C11   C5   C6   120.37  3.000
 R2N  C11   C5   C4   106.66  3.000
 R2N  C6    C5   C4   132.96  3.000
 R2N  H6    C6   C7   121.98  3.000
 R2N  H6    C6   C5   120.35  3.000
 R2N  C7    C6   C5   117.67  3.000
 R2N  C9    C7   BR8  118.36  3.000
 R2N  C9    C7   C6   122.16  3.000
 R2N  BR8   C7   C6   119.47  3.000
 R2N  H9    C9   C10  119.13  3.000
 R2N  C10   C9   C7   120.72  3.000
 R2N  H9    C9   C7   120.15  3.000
 R2N  H10   C10  C11  122.57  3.000
 R2N  C11   C10  C9   118.06  3.000
 R2N  H10   C10  C9   119.36  3.000
 R2N  C10   C11  C5   121.00  3.000
 R2N  C10   C11  N2   130.36  3.000
 R2N  C5    C11  N2   108.63  3.000
 R2N  O14   C12  O13  123.56  3.000
 R2N  O14   C12  C3   114.55  3.000
 R2N  O13   C12  C3   121.89  3.000
 R2N  HO14  O14  C12  109.96  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
 R2N  CONST_01  C4    C5   C11  N2     0.00   0.0  0
 R2N  CONST_02  C6    C5   C11  N2   180.00   0.0  0
 R2N  CONST_03  C9    C10  C11  N2   180.00   0.0  0
 R2N  CONST_04  C5    C4   C3   N2     0.00   0.0  0
 R2N  CONST_05  C5    C11  N2   C3     0.00   0.0  0
 R2N  CONST_06  C10   C11  N2   C3   180.00   0.0  0
 R2N  CONST_07  C6    C5   C4   C3   180.00   0.0  0
 R2N  CONST_08  C11   C5   C4   C3     0.00   0.0  0
 R2N  CONST_09  C11   N2   C3   C4     0.00   0.0  0
 R2N  CONST_10  C7    C6   C5   C4   180.00   0.0  0
 R2N  CONST_11  C10   C11  C5   C4   180.00   0.0  0
 R2N  CONST_12  C9    C7   C6   C5     0.00   0.0  0
 R2N  CONST_13  C9    C10  C11  C5     0.00   0.0  0
 R2N  CONST_14  C10   C11  C5   C6     0.00   0.0  0
 R2N  CONST_15  C10   C9   C7   C6     0.00   0.0  0
 R2N  CONST_16  C11   C5   C6   C7     0.00   0.0  0
 R2N  CONST_17  C11   C10  C9   C7     0.00   0.0  0
 R2N  CONST_18  C5    C11  N2   C1   180.00   0.0  0
 R2N  CONST_19  C10   C11  N2   C1     0.00   0.0  0
 R2N  CONST_20  C4    C3   N2   C1   180.00   0.0  0
 R2N  CONST_21  C12   C3   C4   C5   180.00   0.0  0
 R2N  CONST_22  BR8   C7   C6   C5   180.00   0.0  0
 R2N  CONST_23  C10   C9   C7   BR8  180.00   0.0  0
 R2N  CONST_24  C12   C3   N2   C11  180.00   0.0  0
 R2N  CONST_25  H10   C10  C11  N2     0.00   0.0  0
 R2N  CONST_26  H4    C4   C3   N2   180.00   0.0  0
 R2N  CONST_27  H6    C6   C5   C4     0.00   0.0  0
 R2N  CONST_28  H9    C9   C7   C6   180.00   0.0  0
 R2N  CONST_29  HO14  O14  C12  C3   180.00   0.0  0
 R2N  Var_01    O13   C12  C3   N2   179.80  30.0  2
 R2N  Var_02    H1    C1   N2   C3   -60.60  30.0  2

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
 R2N  plan-1  C1    0.020
 R2N  plan-1  N2    0.020
 R2N  plan-1  C3    0.020
 R2N  plan-1  C4    0.020
 R2N  plan-1  C5    0.020
 R2N  plan-1  C6    0.020
 R2N  plan-1  C7    0.020
 R2N  plan-1  BR8   0.020
 R2N  plan-1  C9    0.020
 R2N  plan-1  C10   0.020
 R2N  plan-1  C11   0.020
 R2N  plan-1  C12   0.020
 R2N  plan-1  H4    0.020
 R2N  plan-1  H6    0.020
 R2N  plan-1  H9    0.020
 R2N  plan-1  H10   0.020
 R2N  plan-2  C3    0.020
 R2N  plan-2  C12   0.020
 R2N  plan-2  O13   0.020
 R2N  plan-2  O14   0.020
 R2N  plan-2  HO14  0.020

