# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB551_0m
_database_code_depnum_ccdc_archive 'CCDC 2240369'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-09-26 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Domperidone nicotinate hydrate'
_chemical_name_common            'Domperidone nicotinate hydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         
'C22 H25 Cl N5 O2, C6 H4 N O2, 2(H2 O), 0.805(O)'
_chemical_formula_sum            'C28 H33 Cl N6 O6.81'
_chemical_formula_weight         597.93

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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3734(18)
_cell_length_b                   10.207(2)
_cell_length_c                   21.402(5)
_cell_angle_alpha                99.812(5)
_cell_angle_beta                 98.717(5)
_cell_angle_gamma                102.962(6)
_cell_volume                     1516.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      24.8

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             628.9
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.179
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6627
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            47136
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.118
_diffrn_reflns_theta_max         30.613
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9274
_reflns_number_gt                4761
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0944P)²+0.3852P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9274
_refine_ls_number_parameters     462
_refine_ls_number_restraints     271
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.2079
_refine_ls_wR_factor_gt          0.1594
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2344(3) 1.1031(2) 0.51153(11) 0.0481(5) Uani 1 1 d . . . . .
C2 C 1.2361(3) 1.0071(2) 0.45780(10) 0.0463(4) Uani 1 1 d . . . . .
H2 H 1.219045 1.025089 0.416450 0.056 Uiso 1 1 calc R U . . .
C3 C 1.2644(2) 0.88275(19) 0.46866(9) 0.0414(4) Uani 1 1 d . . . . .
C4 C 1.2906(3) 0.85554(19) 0.53078(9) 0.0417(4) Uani 1 1 d . . . . .
C5 C 1.2864(3) 0.9521(2) 0.58357(10) 0.0501(5) Uani 1 1 d . . . . .
H5 H 1.301809 0.934067 0.624928 0.060 Uiso 1 1 calc R U . . .
C6 C 1.2583(3) 1.0781(2) 0.57314(11) 0.0522(5) Uani 1 1 d . . . . .
H6 H 1.255632 1.145536 0.607963 0.063 Uiso 1 1 calc R U . . .
C7 C 1.3016(3) 0.6675(2) 0.45853(9) 0.0431(4) Uani 1 1 d . . . . .
C8 C 1.3402(3) 0.6407(2) 0.57262(9) 0.0437(4) Uani 1 1 d . . . . .
H8 H 1.367435 0.556305 0.551365 0.052 Uiso 1 1 calc R U . . .
C9 C 1.5055(3) 0.7112(2) 0.62866(10) 0.0505(5) Uani 1 1 d . . . . .
H9A H 1.621587 0.734910 0.612258 0.061 Uiso 1 1 calc R U . . .
H9B H 1.483742 0.795473 0.651062 0.061 Uiso 1 1 calc R U . . .
C10 C 1.5267(3) 0.6173(2) 0.67517(10) 0.0502(5) Uani 1 1 d . . . . .
H10A H 1.559168 0.536728 0.653498 0.060 Uiso 1 1 calc R U . . .
H10B H 1.629840 0.664822 0.711351 0.060 Uiso 1 1 calc R U . . .
C11 C 1.1834(3) 0.5059(2) 0.64543(10) 0.0552(5) Uani 1 1 d . . . . .
H11A H 1.068527 0.484186 0.662650 0.066 Uiso 1 1 calc R U . . .
H11B H 1.201945 0.420398 0.623066 0.066 Uiso 1 1 calc R U . . .
C12 C 1.1597(3) 0.5978(2) 0.59780(10) 0.0516(5) Uani 1 1 d . . . . .
H12A H 1.056397 0.549110 0.561875 0.062 Uiso 1 1 calc R U . . .
H12B H 1.127430 0.679066 0.618867 0.062 Uiso 1 1 calc R U . . .
C13 C 1.3689(3) 0.4793(2) 0.74539(10) 0.0559(5) Uani 1 1 d . . . . .
H13A H 1.413301 0.403555 0.724749 0.067 Uiso 1 1 calc R U . . .
H13B H 1.245661 0.441264 0.754771 0.067 Uiso 1 1 calc R U . . .
C14 C 1.5062(3) 0.5520(3) 0.80820(10) 0.0624(6) Uani 1 1 d . . . . .
H14A H 1.635496 0.564884 0.801269 0.075 Uiso 1 1 calc R U . . .
H14B H 1.485671 0.641940 0.822551 0.075 Uiso 1 1 calc R U . . .
C15 C 1.4787(4) 0.4687(3) 0.85969(11) 0.0691(7) Uani 1 1 d . . . . .
H15A H 1.346851 0.449775 0.864096 0.083 Uiso 1 1 calc R U . . .
H15B H 1.508369 0.381452 0.846614 0.083 Uiso 1 1 calc R U . . .
C16 C 1.7665(4) 0.5163(3) 0.94673(12) 0.0750(8) Uani 1 1 d . . . . .
C17 C 1.7191(4) 0.6909(3) 1.01591(12) 0.0703(7) Uani 1 1 d . . . . .
C18 C 1.7299(5) 0.7979(3) 1.06661(16) 0.0922(9) Uani 1 1 d . . . . .
H18 H 1.831366 0.825840 1.101670 0.111 Uiso 1 1 calc R U . . .
C19 C 1.5843(7) 0.8608(4) 1.0628(2) 0.1192(13) Uani 1 1 d . . . . .
H19 H 1.586812 0.932636 1.096365 0.143 Uiso 1 1 calc R U . . .
C20 C 1.4338(6) 0.8210(4) 1.0108(2) 0.1179(13) Uani 1 1 d . . . . .
H20 H 1.338582 0.867397 1.009909 0.142 Uiso 1 1 calc R U . . .
C21 C 1.4216(5) 0.7140(4) 0.95994(16) 0.0905(9) Uani 1 1 d . . . . .
H21 H 1.320146 0.686531 0.924887 0.109 Uiso 1 1 calc R U . . .
C22 C 1.5672(4) 0.6499(3) 0.96380(12) 0.0682(7) Uani 1 1 d . . . . .
Cl1 Cl 1.20027(8) 1.26113(6) 0.49944(3) 0.06285(19) Uani 1 1 d . . . . .
N1 N 1.2702(2) 0.76671(17) 0.42603(9) 0.0458(4) Uani 1 1 d . . . . .
H1N H 1.273(3) 0.759(2) 0.3861(13) 0.060(7) Uiso 1 1 d . . . . .
N2 N 1.3155(2) 0.72230(16) 0.52377(7) 0.0437(4) Uani 1 1 d . . . . .
N3 N 1.3484(2) 0.57292(19) 0.69996(8) 0.0454(4) Uani 1 1 d . . . . .
H3N H 1.320(3) 0.651(3) 0.7221(12) 0.062(7) Uiso 1 1 d . . . . .
N4 N 1.5993(3) 0.5416(2) 0.92169(9) 0.0679(6) Uani 1 1 d . . . . .
N5 N 1.8388(4) 0.6076(3) 1.00390(10) 0.0765(7) Uani 1 1 d . . . . .
H5N H 1.948(5) 0.604(3) 1.0300(17) 0.105(11) Uiso 1 1 d . . . . .
O1 O 1.3119(2) 0.55205(15) 0.43550(7) 0.0538(4) Uani 1 1 d . . . . .
O2 O 1.8387(3) 0.4280(3) 0.92123(9) 0.1001(7) Uani 1 1 d . . . . .
C23 C 1.1399(9) 0.7849(6) 0.7821(3) 0.0796(16) Uani 0.776(4) 1 d . U P A 1
O3 O 1.2447(5) 0.8174(5) 0.74555(19) 0.1012(12) Uani 0.776(4) 1 d . U P A 1
O4 O 1.1400(7) 0.6839(5) 0.8091(3) 0.1240(15) Uani 0.776(4) 1 d . U P A 1
C23D C 1.157(3) 0.828(2) 0.7695(11) 0.074(3) Uani 0.224(4) 1 d D U P A 2
O4D O 1.184(2) 0.7114(13) 0.7815(5) 0.075(3) Uani 0.224(4) 1 d . U P A 2
O3D O 1.232(2) 0.8879(12) 0.7329(6) 0.096(4) Uani 0.224(4) 1 d . U P A 2
C24 C 1.0023(4) 0.8677(3) 0.79637(15) 0.0714(10) Uani 0.776(4) 1 d G U P A 1
C25 C 0.9114(4) 0.8548(3) 0.84821(14) 0.0805(10) Uani 0.776(4) 1 d G U P A 1
H25 H 0.940308 0.797130 0.875386 0.097 Uiso 0.776(4) 1 calc R U P A 1
C26 C 0.7775(5) 0.9279(3) 0.85942(15) 0.0965(12) Uani 0.776(4) 1 d G U P A 1
H26 H 0.716753 0.919228 0.894104 0.116 Uiso 0.776(4) 1 calc R U P A 1
C27 C 0.7344(4) 1.0140(3) 0.81880(17) 0.1079(14) Uani 0.776(4) 1 d G U P A 1
H27 H 0.644753 1.062985 0.826302 0.129 Uiso 0.776(4) 1 calc R U P A 1
N6 N 0.8252(4) 1.0270(3) 0.76696(15) 0.1013(11) Uani 0.776(4) 1 d G U P A 1
C28 C 0.9591(4) 0.9539(3) 0.75575(13) 0.0859(11) Uani 0.776(4) 1 d G U P A 1
H28 H 1.019864 0.962548 0.721062 0.103 Uiso 0.776(4) 1 calc R U P A 1
C24D C 1.0153(17) 0.8686(13) 0.8075(6) 0.078(2) Uani 0.224(4) 1 d DG U P A 2
C28D C 0.9996(15) 0.8440(11) 0.8686(5) 0.088(2) Uani 0.224(4) 1 d G U P A 2
H28D H 1.066972 0.787660 0.886282 0.106 Uiso 0.224(4) 1 calc R U P A 2
N6D N 0.8832(15) 0.9035(10) 0.9034(4) 0.106(2) Uani 0.224(4) 1 d G U P A 2
C27D C 0.7825(16) 0.9876(12) 0.8770(6) 0.103(2) Uani 0.224(4) 1 d G U P A 2
H27D H 0.704577 1.027450 0.900273 0.124 Uiso 0.224(4) 1 calc R U P A 2
C26D C 0.7982(16) 1.0123(12) 0.8159(6) 0.090(2) Uani 0.224(4) 1 d G U P A 2
H26D H 0.730795 1.068609 0.798284 0.108 Uiso 0.224(4) 1 calc R U P A 2
C25D C 0.9146(17) 0.9528(13) 0.7812(5) 0.088(2) Uani 0.224(4) 1 d G U P A 2
H25D H 0.925102 0.969293 0.740293 0.106 Uiso 0.224(4) 1 calc R U P A 2
O1W O 0.7275(5) 0.2376(3) 0.70617(11) 0.1305(10) Uani 1 1 d D . . . .
H1W H 0.768(7) 0.299(4) 0.7425(15) 0.196 Uiso 1 1 d D U . . .
H2W H 0.835(4) 0.222(6) 0.698(3) 0.196 Uiso 1 1 d D U . . .
O2W O 0.9416(5) 0.4431(4) 0.80281(14) 0.1511(13) Uani 1 1 d D . . . .
H3W H 0.904(8) 0.431(6) 0.8381(16) 0.227 Uiso 1 1 d D U . . .
H4W H 1.032(7) 0.517(4) 0.812(3) 0.227 Uiso 1 1 d D U . . .
O3W O 1.3863(8) 0.1417(6) 0.7494(2) 0.211(4) Uani 0.805(12) 1 d . . P B 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.378(3) . ?
C1 C2 1.382(3) . ?
C1 Cl1 1.742(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.380(3) . ?
C3 C4 1.398(3) . ?
C4 C5 1.376(3) . ?
C4 N2 1.399(2) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.221(2) . ?
C7 N1 1.364(3) . ?
C7 N2 1.392(2) . ?
C8 N2 1.459(2) . ?
C8 C12 1.513(3) . ?
C8 C9 1.520(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.509(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N3 1.497(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.495(3) . ?
C11 C12 1.515(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.489(3) . ?
C13 C14 1.514(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.512(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N4 1.454(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.237(3) . ?
C16 N5 1.357(4) . ?
C16 N4 1.365(3) . ?
C17 N5 1.378(4) . ?
C17 C18 1.381(4) . ?
C17 C22 1.388(4) . ?
C18 C19 1.368(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(4) . ?
C21 H21 0.9300 . ?
C22 N4 1.390(3) . ?
N1 H1N 0.85(3) . ?
N3 H3N 0.94(3) . ?
N5 H5N 0.92(4) . ?
C23 O3 1.215(7) . ?
C23 O4 1.265(7) . ?
C23 C24 1.494(6) . ?
C23D O3D 1.20(2) . ?
C23D O4D 1.31(2) . ?
C23D C24D 1.504(10) . ?
C24 C25 1.3900 . ?
C24 C28 1.3900 . ?
C25 C26 1.3900 . ?
C25 H25 0.9300 . ?
C26 C27 1.3900 . ?
C26 H26 0.9300 . ?
C27 N6 1.3900 . ?
C27 H27 0.9300 . ?
N6 C28 1.3900 . ?
C28 H28 0.9300 . ?
C24D C28D 1.3900 . ?
C24D C25D 1.3900 . ?
C28D N6D 1.3900 . ?
C28D H28D 0.9300 . ?
N6D C27D 1.3900 . ?
C27D C26D 1.3900 . ?
C27D H27D 0.9300 . ?
C26D C25D 1.3900 . ?
C26D H26D 0.9300 . ?
C25D H25D 0.9300 . ?
O1W H1W 0.875(10) . ?
O1W H2W 0.879(10) . ?
O2W H3W 0.863(10) . ?
O2W H4W 0.857(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.60(19) . . ?
C6 C1 Cl1 119.76(17) . . ?
C2 C1 Cl1 117.65(16) . . ?
C1 C2 C3 116.58(19) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
N1 C3 C2 130.71(18) . . ?
N1 C3 C4 107.46(17) . . ?
C2 C3 C4 121.82(18) . . ?
C5 C4 C3 120.65(18) . . ?
C5 C4 N2 132.94(18) . . ?
C3 C4 N2 106.41(16) . . ?
C4 C5 C6 117.97(19) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 N1 127.36(18) . . ?
O1 C7 N2 126.17(18) . . ?
N1 C7 N2 106.45(17) . . ?
N2 C8 C12 111.39(16) . . ?
N2 C8 C9 113.66(16) . . ?
C12 C8 C9 110.11(16) . . ?
N2 C8 H8 107.1 . . ?
C12 C8 H8 107.1 . . ?
C9 C8 H8 107.1 . . ?
C10 C9 C8 110.21(17) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N3 C10 C9 111.81(16) . . ?
N3 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N3 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N3 C11 C12 111.75(17) . . ?
N3 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C8 C12 C11 110.88(17) . . ?
C8 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N3 C13 C14 112.40(19) . . ?
N3 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N3 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 110.4(2) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N4 C15 C14 111.3(2) . . ?
N4 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
N4 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O2 C16 N5 126.9(3) . . ?
O2 C16 N4 126.1(3) . . ?
N5 C16 N4 107.0(3) . . ?
N5 C17 C18 132.1(3) . . ?
N5 C17 C22 106.7(2) . . ?
C18 C17 C22 121.2(3) . . ?
C19 C18 C17 116.8(3) . . ?
C19 C18 H18 121.6 . . ?
C17 C18 H18 121.6 . . ?
C18 C19 C20 122.2(4) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C19 C20 C21 121.4(4) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 116.6(3) . . ?
C22 C21 H21 121.7 . . ?
C20 C21 H21 121.7 . . ?
C21 C22 C17 121.8(3) . . ?
C21 C22 N4 131.3(3) . . ?
C17 C22 N4 106.9(2) . . ?
C7 N1 C3 110.42(17) . . ?
C7 N1 H1N 121.9(17) . . ?
C3 N1 H1N 127.0(17) . . ?
C7 N2 C4 109.25(15) . . ?
C7 N2 C8 121.22(16) . . ?
C4 N2 C8 129.41(16) . . ?
C13 N3 C11 110.35(16) . . ?
C13 N3 C10 111.75(16) . . ?
C11 N3 C10 110.99(16) . . ?
C13 N3 H3N 108.3(15) . . ?
C11 N3 H3N 106.5(15) . . ?
C10 N3 H3N 108.8(15) . . ?
C16 N4 C22 109.2(2) . . ?
C16 N4 C15 124.7(2) . . ?
C22 N4 C15 126.0(2) . . ?
C16 N5 C17 110.2(2) . . ?
C16 N5 H5N 121(2) . . ?
C17 N5 H5N 129(2) . . ?
O3 C23 O4 123.7(6) . . ?
O3 C23 C24 118.8(5) . . ?
O4 C23 C24 117.5(5) . . ?
O3D C23D O4D 124.1(12) . . ?
O3D C23D C24D 127.2(16) . . ?
O4D C23D C24D 108.7(14) . . ?
C25 C24 C28 120.0 . . ?
C25 C24 C23 120.5(3) . . ?
C28 C24 C23 119.5(3) . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
N6 C27 C26 120.0 . . ?
N6 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 N6 C28 120.0 . . ?
N6 C28 C24 120.0 . . ?
N6 C28 H28 120.0 . . ?
C24 C28 H28 120.0 . . ?
C28D C24D C25D 120.0 . . ?
C28D C24D C23D 124.9(12) . . ?
C25D C24D C23D 114.5(11) . . ?
C24D C28D N6D 120.0 . . ?
C24D C28D H28D 120.0 . . ?
N6D C28D H28D 120.0 . . ?
C28D N6D C27D 120.0 . . ?
C26D C27D N6D 120.0 . . ?
C26D C27D H27D 120.0 . . ?
N6D C27D H27D 120.0 . . ?
C27D C26D C25D 120.0 . . ?
C27D C26D H26D 120.0 . . ?
C25D C26D H26D 120.0 . . ?
C26D C25D C24D 120.0 . . ?
C26D C25D H25D 120.0 . . ?
C24D C25D H25D 120.0 . . ?
H1W O1W H2W 101(2) . . ?
H3W O2W H4W 108(3) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(3) . . . . ?
Cl1 C1 C2 C3 179.68(14) . . . . ?
C1 C2 C3 N1 178.72(19) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
N1 C3 C4 C5 -178.24(18) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
N1 C3 C4 N2 1.1(2) . . . . ?
C2 C3 C4 N2 -179.73(17) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
N2 C4 C5 C6 179.8(2) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
Cl1 C1 C6 C5 -179.78(16) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
N2 C8 C9 C10 -177.29(17) . . . . ?
C12 C8 C9 C10 56.9(2) . . . . ?
C8 C9 C10 N3 -57.0(2) . . . . ?
N2 C8 C12 C11 176.52(16) . . . . ?
C9 C8 C12 C11 -56.4(2) . . . . ?
N3 C11 C12 C8 55.8(2) . . . . ?
N3 C13 C14 C15 162.7(2) . . . . ?
C13 C14 C15 N4 -175.7(2) . . . . ?
N5 C17 C18 C19 179.3(4) . . . . ?
C22 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C20 -0.6(6) . . . . ?
C18 C19 C20 C21 0.8(7) . . . . ?
C19 C20 C21 C22 -0.3(6) . . . . ?
C20 C21 C22 C17 -0.3(5) . . . . ?
C20 C21 C22 N4 -179.4(3) . . . . ?
N5 C17 C22 C21 -179.0(3) . . . . ?
C18 C17 C22 C21 0.5(4) . . . . ?
N5 C17 C22 N4 0.3(3) . . . . ?
C18 C17 C22 N4 179.8(3) . . . . ?
O1 C7 N1 C3 178.83(19) . . . . ?
N2 C7 N1 C3 0.2(2) . . . . ?
C2 C3 N1 C7 -179.85(19) . . . . ?
C4 C3 N1 C7 -0.8(2) . . . . ?
O1 C7 N2 C4 -178.13(19) . . . . ?
N1 C7 N2 C4 0.6(2) . . . . ?
O1 C7 N2 C8 -1.7(3) . . . . ?
N1 C7 N2 C8 177.01(16) . . . . ?
C5 C4 N2 C7 178.2(2) . . . . ?
C3 C4 N2 C7 -1.1(2) . . . . ?
C5 C4 N2 C8 2.1(3) . . . . ?
C3 C4 N2 C8 -177.12(18) . . . . ?
C12 C8 N2 C7 -106.5(2) . . . . ?
C9 C8 N2 C7 128.44(19) . . . . ?
C12 C8 N2 C4 69.2(2) . . . . ?
C9 C8 N2 C4 -55.9(3) . . . . ?
C14 C13 N3 C11 -167.99(19) . . . . ?
C14 C13 N3 C10 68.0(2) . . . . ?
C12 C11 N3 C13 -179.35(18) . . . . ?
C12 C11 N3 C10 -54.9(2) . . . . ?
C9 C10 N3 C13 179.49(17) . . . . ?
C9 C10 N3 C11 55.8(2) . . . . ?
O2 C16 N4 C22 -179.0(3) . . . . ?
N5 C16 N4 C22 0.0(3) . . . . ?
O2 C16 N4 C15 -0.8(5) . . . . ?
N5 C16 N4 C15 178.2(2) . . . . ?
C21 C22 N4 C16 179.1(3) . . . . ?
C17 C22 N4 C16 -0.2(3) . . . . ?
C21 C22 N4 C15 0.9(5) . . . . ?
C17 C22 N4 C15 -178.4(2) . . . . ?
C14 C15 N4 C16 -100.7(3) . . . . ?
C14 C15 N4 C22 77.2(3) . . . . ?
O2 C16 N5 C17 179.2(3) . . . . ?
N4 C16 N5 C17 0.2(3) . . . . ?
C18 C17 N5 C16 -179.8(3) . . . . ?
C22 C17 N5 C16 -0.4(3) . . . . ?
O3 C23 C24 C25 -165.3(4) . . . . ?
O4 C23 C24 C25 14.8(7) . . . . ?
O3 C23 C24 C28 17.5(7) . . . . ?
O4 C23 C24 C28 -162.4(4) . . . . ?
C28 C24 C25 C26 0.0 . . . . ?
C23 C24 C25 C26 -177.2(4) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 N6 0.0 . . . . ?
C26 C27 N6 C28 0.0 . . . . ?
C27 N6 C28 C24 0.0 . . . . ?
C25 C24 C28 N6 0.0 . . . . ?
C23 C24 C28 N6 177.3(4) . . . . ?
O3D C23D C24D C28D -147(2) . . . . ?
O4D C23D C24D C28D 34(2) . . . . ?
O3D C23D C24D C25D 24(3) . . . . ?
O4D C23D C24D C25D -154.6(15) . . . . ?
C25D C24D C28D N6D 0.0 . . . . ?
C23D C24D C28D N6D 170.6(16) . . . . ?
C24D C28D N6D C27D 0.0 . . . . ?
C28D N6D C27D C26D 0.0 . . . . ?
N6D C27D C26D C25D 0.0 . . . . ?
C27D C26D C25D C24D 0.0 . . . . ?
C28D C24D C25D C26D 0.0 . . . . ?
C23D C24D C25D C26D -171.5(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1W 0.85(3) 1.98(3) 2.825(3) 173(2) 2_766 yes
N3 H3N O3^a 0.94(3) 1.92(3) 2.831(4) 165(2) . yes
N3 H3N O4^a 0.94(3) 2.47(3) 3.172(6) 132.2(19) . yes
N3 H3N O4D^b 0.94(3) 1.85(3) 2.660(12) 144(2) . yes
N3 H3N O3D^b 0.94(3) 2.63(3) 3.496(12) 155.0(19) . yes
N5 H5N O2 0.92(4) 1.87(4) 2.790(3) 172(3) 2_967 yes
O1W H1W O2W 0.875(10) 1.86(2) 2.686(4) 156(5) . yes
O2W H3W O2 0.863(10) 1.915(14) 2.772(4) 172(6) 1_455 yes
O2W H4W O4^a 0.857(10) 1.73(3) 2.532(7) 156(7) . yes
O2W H4W O4D^b 0.857(10) 2.30(3) 3.063(13) 149(6) . yes

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB707_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2240372'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-09-26 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Domperidone mandelate dihydrate'
_chemical_name_common            'Domperidone mandelate dihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 Cl N5 O2, C8 H7 O3, 2(H2 O)'
_chemical_formula_sum            'C30 H36 Cl N5 O7'
_chemical_formula_weight         614.09

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 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3478(2)
_cell_length_b                   12.5278(2)
_cell_length_c                   25.5542(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.6760(10)
_cell_angle_gamma                90
_cell_volume                     2991.30(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7500
_cell_measurement_theta_min      2.277
_cell_measurement_theta_max      21.40

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4450
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            41578
_diffrn_reflns_av_unetI/netI     0.1177
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.277
_diffrn_reflns_theta_max         31.072
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             8786
_reflns_number_gt                3419
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0878P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8786
_refine_ls_number_parameters     435
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1754
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1928
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4002(3) 0.63280(19) 0.51809(9) 0.0496(6) Uani 1 1 d . . . . .
C2 C 0.3537(3) 0.64587(19) 0.46638(10) 0.0520(6) Uani 1 1 d . . . . .
H2 H 0.256253 0.649748 0.458196 0.062 Uiso 1 1 calc R U . . .
C3 C 0.4528(3) 0.65326(19) 0.42649(9) 0.0491(6) Uani 1 1 d . . . . .
H3 H 0.423024 0.662232 0.391730 0.059 Uiso 1 1 calc R U . . .
C4 C 0.5960(3) 0.64677(18) 0.44053(8) 0.0429(6) Uani 1 1 d . . . . .
C5 C 0.6398(3) 0.63105(18) 0.49276(9) 0.0427(6) Uani 1 1 d . . . . .
C6 C 0.5423(3) 0.62392(18) 0.53260(9) 0.0489(6) Uani 1 1 d . . . . .
H6 H 0.571719 0.613654 0.567319 0.059 Uiso 1 1 calc R U . . .
C7 C 0.8390(3) 0.63962(18) 0.44536(9) 0.0434(6) Uani 1 1 d . . . . .
C8 C 0.7363(3) 0.67625(19) 0.35560(8) 0.0425(6) Uani 1 1 d . . . . .
H8 H 0.838318 0.687121 0.349579 0.051 Uiso 1 1 calc R U . . .
C9 C 0.6861(3) 0.5844(2) 0.32110(8) 0.0493(6) Uani 1 1 d . . . . .
H9A H 0.586589 0.568931 0.327727 0.059 Uiso 1 1 calc R U . . .
H9B H 0.741867 0.521159 0.329786 0.059 Uiso 1 1 calc R U . . .
C10 C 0.7018(3) 0.6107(2) 0.26319(8) 0.0499(6) Uani 1 1 d . . . . .
H10A H 0.802428 0.618630 0.255791 0.060 Uiso 1 1 calc R U . . .
H10B H 0.663926 0.552269 0.242080 0.060 Uiso 1 1 calc R U . . .
Cl1 Cl 0.27164(8) 0.62547(6) 0.56630(3) 0.0681(3) Uani 1 1 d . . . . .
C11 C 0.6745(3) 0.80251(19) 0.28247(8) 0.0474(6) Uani 1 1 d . . . . .
H11A H 0.619256 0.865742 0.273386 0.057 Uiso 1 1 calc R U . . .
H11B H 0.774102 0.817333 0.275706 0.057 Uiso 1 1 calc R U . . .
C12 C 0.6591(3) 0.77844(19) 0.34026(8) 0.0457(6) Uani 1 1 d . . . . .
H12A H 0.698147 0.837210 0.360846 0.055 Uiso 1 1 calc R U . . .
H12B H 0.558443 0.771711 0.347856 0.055 Uiso 1 1 calc R U . . .
C13 C 0.6373(3) 0.7429(2) 0.19233(8) 0.0540(7) Uani 1 1 d . . . . .
H13A H 0.734028 0.768090 0.187305 0.065 Uiso 1 1 calc R U . . .
H13B H 0.573100 0.802370 0.185245 0.065 Uiso 1 1 calc R U . . .
C14 C 0.6045(3) 0.6556(2) 0.15231(9) 0.0548(7) Uani 1 1 d . . . . .
H14A H 0.619670 0.683917 0.117582 0.066 Uiso 1 1 calc R U . . .
H14B H 0.671641 0.597501 0.158100 0.066 Uiso 1 1 calc R U . . .
C15 C 0.4545(3) 0.6116(2) 0.15393(9) 0.0517(6) Uani 1 1 d . . . . .
H15A H 0.436455 0.586064 0.188951 0.062 Uiso 1 1 calc R U . . .
H15B H 0.386379 0.668051 0.145720 0.062 Uiso 1 1 calc R U . . .
C16 C 0.4712(3) 0.4210(2) 0.12802(10) 0.0534(7) Uani 1 1 d . . . . .
C17 C 0.3724(3) 0.4261(2) 0.04635(9) 0.0468(6) Uani 1 1 d . . . . .
C18 C 0.3174(3) 0.4052(2) -0.00324(10) 0.0579(7) Uani 1 1 d . . . . .
H18 H 0.316869 0.336451 -0.016964 0.069 Uiso 1 1 calc R U . . .
C19 C 0.2633(3) 0.4901(2) -0.03162(10) 0.0598(7) Uani 1 1 d . . . . .
H19 H 0.225689 0.478256 -0.065204 0.072 Uiso 1 1 calc R U . . .
C20 C 0.2634(3) 0.5917(2) -0.01176(10) 0.0580(7) Uani 1 1 d . . . . .
H20 H 0.224859 0.646845 -0.032026 0.070 Uiso 1 1 calc R U . . .
C21 C 0.3194(3) 0.6141(2) 0.03769(9) 0.0507(6) Uani 1 1 d . . . . .
H21 H 0.320210 0.683170 0.051002 0.061 Uiso 1 1 calc R U . . .
C22 C 0.3741(3) 0.52939(19) 0.06644(9) 0.0435(6) Uani 1 1 d . . . . .
N1 N 0.7876(2) 0.62565(16) 0.49421(8) 0.0463(5) Uani 1 1 d . . . . .
H1N H 0.838(2) 0.6104(17) 0.5244(9) 0.038(6) Uiso 1 1 d . . . . .
N2 N 0.7214(2) 0.65319(15) 0.41176(7) 0.0430(5) Uani 1 1 d . . . . .
N3 N 0.6242(2) 0.71119(16) 0.24876(7) 0.0427(5) Uani 1 1 d . . . . .
H3N H 0.536(3) 0.703(2) 0.2541(9) 0.055(8) Uiso 1 1 d . . . . .
N4 N 0.4343(2) 0.52471(16) 0.11676(7) 0.0458(5) Uani 1 1 d . . . . .
N5 N 0.4315(3) 0.3610(2) 0.08532(9) 0.0557(6) Uani 1 1 d . . . . .
H5N H 0.458(4) 0.293(3) 0.0818(12) 0.090(11) Uiso 1 1 d . . . . .
O1 O 0.96550(18) 0.64078(13) 0.43230(6) 0.0519(4) Uani 1 1 d . . . . .
O2 O 0.5300(2) 0.39102(16) 0.16930(7) 0.0726(6) Uani 1 1 d . . . . .
C23 C 0.2726(3) 0.7244(3) 0.25763(11) 0.0582(7) Uani 1 1 d . . . . .
C25 C 0.0857(3) 0.6353(2) 0.20355(10) 0.0543(7) Uani 1 1 d . . . . .
C26 C 0.1195(3) 0.5275(3) 0.20352(12) 0.0641(8) Uani 1 1 d . . . . .
H26 H 0.152106 0.494675 0.234273 0.077 Uiso 1 1 calc R U . . .
C27 C 0.1049(3) 0.4685(3) 0.15786(13) 0.0714(9) Uani 1 1 d . . . . .
H27 H 0.128494 0.396413 0.158252 0.086 Uiso 1 1 calc R U . . .
C28 C 0.0567(3) 0.5142(3) 0.11249(13) 0.0725(9) Uani 1 1 d . . . . .
H28 H 0.047852 0.473950 0.081997 0.087 Uiso 1 1 calc R U . . .
C29 C 0.0213(3) 0.6205(3) 0.11215(11) 0.0714(9) Uani 1 1 d . . . . .
H29 H -0.013365 0.652008 0.081358 0.086 Uiso 1 1 calc R U . . .
C30 C 0.0366(3) 0.6811(2) 0.15713(11) 0.0636(7) Uani 1 1 d . . . . .
H30 H 0.013675 0.753371 0.156208 0.076 Uiso 1 1 calc R U . . .
C24 C 0.112(2) 0.7150(10) 0.2517(7) 0.046(3) Uani 0.562(5) 1 d . . P A 1
H24 H 0.078484 0.678368 0.282993 0.055 Uiso 0.562(5) 1 calc R U P A 1
O3 O 0.0285(5) 0.7943(4) 0.24369(15) 0.0893(17) Uani 0.562(5) 1 d . . P A 1
H3A H 0.035817 0.835778 0.268460 0.134 Uiso 0.562(5) 1 calc R U P A 1
C24D C 0.111(3) 0.6804(13) 0.2536(10) 0.054(4) Uani 0.438(5) 1 d . . P A 2
H24D H 0.057985 0.747537 0.249850 0.065 Uiso 0.438(5) 1 calc R U P A 2
O3D O 0.0624(6) 0.6451(5) 0.3008(2) 0.097(2) Uani 0.438(5) 1 d . . P A 2
H3DA H 0.129207 0.619429 0.318149 0.146 Uiso 0.438(5) 1 calc R U P A 2
O4 O 0.3204(2) 0.80102(18) 0.23362(8) 0.0784(6) Uani 1 1 d . . . . .
O5 O 0.3486(2) 0.65983(18) 0.28305(8) 0.0796(6) Uani 1 1 d . . . . .
O1W O 0.0821(3) 0.4322(2) 0.40855(9) 0.0742(6) Uani 1 1 d D . . . .
H1W H 0.143(3) 0.438(3) 0.3843(11) 0.135(17) Uiso 1 1 d D . . . .
H2W H 0.045(7) 0.495(2) 0.409(3) 0.26(3) Uiso 1 1 d D . . . .
O2W O 0.2999(3) 0.4550(2) 0.33547(9) 0.0885(7) Uani 1 1 d D . . . .
H3W H 0.257(4) 0.407(2) 0.3160(13) 0.133 Uiso 1 1 d D U . . .
H4W H 0.295(4) 0.5183(15) 0.3214(15) 0.133 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.373(4) . ?
C1 C2 1.389(4) . ?
C1 Cl1 1.749(2) . ?
C2 C3 1.400(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.399(3) . ?
C4 N2 1.405(3) . ?
C5 N1 1.382(3) . ?
C5 C6 1.389(3) . ?
C7 O1 1.238(3) . ?
C7 N1 1.362(3) . ?
C7 N2 1.386(3) . ?
C8 N2 1.474(3) . ?
C8 C12 1.516(3) . ?
C8 C9 1.516(3) . ?
C9 C10 1.527(3) . ?
C10 N3 1.494(3) . ?
C11 N3 1.499(3) . ?
C11 C12 1.518(3) . ?
C13 N3 1.504(3) . ?
C13 C14 1.522(3) . ?
C14 C15 1.508(3) . ?
C15 N4 1.454(3) . ?
C16 O2 1.234(3) . ?
C16 N5 1.367(3) . ?
C16 N4 1.373(3) . ?
C17 C18 1.379(3) . ?
C17 N5 1.389(3) . ?
C17 C22 1.392(3) . ?
C18 C19 1.375(4) . ?
C19 C20 1.370(4) . ?
C20 C21 1.383(3) . ?
C21 C22 1.380(3) . ?
C22 N4 1.390(3) . ?
C23 O4 1.230(3) . ?
C23 O5 1.247(3) . ?
C23 C24 1.51(2) . ?
C23 C24D 1.61(3) . ?
C25 C30 1.384(4) . ?
C25 C26 1.388(4) . ?
C25 C24D 1.41(3) . ?
C25 C24 1.598(19) . ?
C26 C27 1.384(4) . ?
C27 C28 1.358(4) . ?
C28 C29 1.372(4) . ?
C29 C30 1.382(4) . ?
C24 O3 1.274(15) . ?
C24D O3D 1.37(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.7(2) . . ?
C6 C1 Cl1 119.01(19) . . ?
C2 C1 Cl1 118.3(2) . . ?
C1 C2 C3 120.3(2) . . ?
C4 C3 C2 117.7(2) . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 N2 132.8(2) . . ?
C5 C4 N2 106.4(2) . . ?
N1 C5 C6 130.8(2) . . ?
N1 C5 C4 107.3(2) . . ?
C6 C5 C4 121.9(2) . . ?
C1 C6 C5 116.6(2) . . ?
O1 C7 N1 127.9(2) . . ?
O1 C7 N2 125.3(2) . . ?
N1 C7 N2 106.8(2) . . ?
N2 C8 C12 111.08(17) . . ?
N2 C8 C9 112.39(19) . . ?
C12 C8 C9 110.74(19) . . ?
C8 C9 C10 111.3(2) . . ?
N3 C10 C9 111.20(18) . . ?
N3 C11 C12 111.73(19) . . ?
C8 C12 C11 111.20(18) . . ?
N3 C13 C14 115.7(2) . . ?
C15 C14 C13 114.4(2) . . ?
N4 C15 C14 111.0(2) . . ?
O2 C16 N5 128.2(3) . . ?
O2 C16 N4 124.8(3) . . ?
N5 C16 N4 107.0(2) . . ?
C18 C17 N5 132.7(2) . . ?
C18 C17 C22 121.0(2) . . ?
N5 C17 C22 106.3(2) . . ?
C19 C18 C17 117.4(2) . . ?
C20 C19 C18 121.8(2) . . ?
C19 C20 C21 121.6(3) . . ?
C22 C21 C20 117.1(2) . . ?
C21 C22 N4 131.2(2) . . ?
C21 C22 C17 121.2(2) . . ?
N4 C22 C17 107.6(2) . . ?
C7 N1 C5 110.4(2) . . ?
C7 N2 C4 109.15(18) . . ?
C7 N2 C8 122.10(19) . . ?
C4 N2 C8 128.67(19) . . ?
C10 N3 C11 111.08(18) . . ?
C10 N3 C13 114.02(19) . . ?
C11 N3 C13 108.44(18) . . ?
C16 N4 C22 109.1(2) . . ?
C16 N4 C15 123.0(2) . . ?
C22 N4 C15 127.9(2) . . ?
C16 N5 C17 110.0(2) . . ?
O4 C23 O5 123.8(3) . . ?
O4 C23 C24 112.7(5) . . ?
O5 C23 C24 123.5(5) . . ?
O4 C23 C24D 126.2(8) . . ?
O5 C23 C24D 109.3(7) . . ?
C30 C25 C26 118.3(3) . . ?
C30 C25 C24D 130.8(8) . . ?
C26 C25 C24D 110.9(8) . . ?
C30 C25 C24 116.1(5) . . ?
C26 C25 C24 125.4(5) . . ?
C27 C26 C25 120.2(3) . . ?
C28 C27 C26 121.1(3) . . ?
C27 C28 C29 119.2(3) . . ?
C28 C29 C30 120.6(3) . . ?
C29 C30 C25 120.6(3) . . ?
O3 C24 C23 123.7(11) . . ?
O3 C24 C25 106.6(13) . . ?
C23 C24 C25 104.7(10) . . ?
O3D C24D C25 128.0(15) . . ?
O3D C24D C23 112.8(18) . . ?
C25 C24D C23 109.1(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1W 0.91(2) 1.92(2) 2.830(3) 171(2) 3_666 yes
N5 H5N O1 0.90(3) 2.07(3) 2.961(3) 174(3) 2_645 yes
O3^a H3A^a O2 0.82 1.86 2.604(4) 151.1 2 yes
O1W H2W O1 0.864(10) 2.06(2) 2.902(3) 165(7) 1_455 yes
O2W H3W O4 0.869(10) 1.961(12) 2.826(3) 173(4) 2_545 yes
N3 H3N O4 0.84(3) 2.41(3) 3.069(3) 136(2) . yes
N3 H3N O5 0.84(3) 2.00(3) 2.820(3) 164(2) . yes
O1W H1W O2W 0.859(10) 1.962(12) 2.817(3) 173(4) . yes
O2W H4W O5 0.872(10) 2.094(16) 2.936(3) 162(4) . yes

_refine_diff_density_max         0.364
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.054


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB866_0m
_database_code_depnum_ccdc_archive 'CCDC 2240373'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-09-26 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Domperidone mandelate'
_chemical_name_common            'Domperidone mandelate'
_chemical_melting_point          ?
_chemical_formula_moiety         
'C22 H25 Cl N5 O2, 0.763(C8 H7 O3), 0.237(C8 H8 O3)'
_chemical_formula_sum            'C30 H32.24 Cl N5 O5'
_chemical_formula_weight         578.29

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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.454(2)
_cell_length_b                   12.248(3)
_cell_length_c                   12.770(3)
_cell_angle_alpha                90.050(7)
_cell_angle_beta                 107.616(6)
_cell_angle_gamma                98.320(6)
_cell_volume                     1393.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4498
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      22.63

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             608.5
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6471
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 QUEST PHOTON-III'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            25733
_diffrn_reflns_av_unetI/netI     0.1009
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.675
_diffrn_reflns_theta_max         29.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7097
_reflns_number_gt                3400
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0852P)²+0.6832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7097
_refine_ls_number_parameters     476
_refine_ls_number_restraints     356
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.2057
_refine_ls_wR_factor_gt          0.1591
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5044(3) 0.0801(3) 0.3736(2) 0.0348(7) Uani 1 1 d . . . . .
C2 C 0.3626(3) 0.0339(3) 0.3745(2) 0.0343(7) Uani 1 1 d . . . . .
H2 H 0.310005 -0.030746 0.330895 0.041 Uiso 1 1 calc R U . . .
C3 C 0.3012(3) 0.0864(3) 0.4420(2) 0.0334(7) Uani 1 1 d . . . . .
C4 C 0.3771(3) 0.1819(3) 0.5059(2) 0.0329(7) Uani 1 1 d . . . . .
C5 C 0.5209(3) 0.2258(3) 0.5055(3) 0.0351(7) Uani 1 1 d . . . . .
H5 H 0.574486 0.289676 0.550105 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5837(3) 0.1740(3) 0.4384(2) 0.0365(8) Uani 1 1 d . . . . .
H6 H 0.681751 0.202516 0.436341 0.044 Uiso 1 1 calc R U . . .
C7 C 0.1541(3) 0.1337(3) 0.5387(3) 0.0388(8) Uani 1 1 d . . . . .
C8 C 0.3106(3) 0.3039(3) 0.6431(3) 0.0389(8) Uani 1 1 d . . . . .
H8 H 0.214808 0.307501 0.660013 0.047 Uiso 1 1 calc R U . . .
C9 C 0.3551(4) 0.4139(3) 0.5982(3) 0.0404(8) Uani 1 1 d . . . . .
H9A H 0.271612 0.428730 0.533863 0.048 Uiso 1 1 calc R U . . .
H9B H 0.443589 0.409931 0.573102 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3923(3) 0.5086(3) 0.6843(3) 0.0421(8) Uani 1 1 d . . . . .
H10A H 0.427700 0.577970 0.654022 0.051 Uiso 1 1 calc R U . . .
H10B H 0.300988 0.518593 0.703587 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4608(4) 0.3799(3) 0.8317(3) 0.0458(9) Uani 1 1 d . . . . .
H11A H 0.369640 0.387648 0.852172 0.055 Uiso 1 1 calc R U . . .
H11B H 0.540092 0.365750 0.899101 0.055 Uiso 1 1 calc R U . . .
C12 C 0.4266(4) 0.2835(3) 0.7489(3) 0.0430(8) Uani 1 1 d . . . . .
H12A H 0.519995 0.271879 0.733470 0.052 Uiso 1 1 calc R U . . .
H12B H 0.389244 0.215573 0.780434 0.052 Uiso 1 1 calc R U . . .
C13 C 0.5628(4) 0.5756(3) 0.8716(3) 0.0443(8) Uani 1 1 d . . . . .
H13A H 0.475552 0.591256 0.893443 0.053 Uiso 1 1 calc R U . . .
H13B H 0.636064 0.551241 0.937247 0.053 Uiso 1 1 calc R U . . .
C14 C 0.6336(4) 0.6794(3) 0.8347(3) 0.0513(9) Uani 1 1 d . . . . .
H14A H 0.555466 0.723290 0.795128 0.062 Uiso 1 1 calc R U . . .
H14B H 0.689500 0.661538 0.784336 0.062 Uiso 1 1 calc R U . . .
C15 C 0.7427(4) 0.7465(3) 0.9385(3) 0.0512(9) Uani 1 1 d . . . . .
H15A H 0.716683 0.719347 1.004403 0.061 Uiso 1 1 calc R U . . .
H15B H 0.846448 0.733729 0.946822 0.061 Uiso 1 1 calc R U . . .
C16 C 0.6414(3) 0.9112(3) 0.9729(3) 0.0383(8) Uani 1 1 d . . . . .
C17 C 0.7817(3) 1.0437(3) 0.9103(3) 0.0365(8) Uani 1 1 d . . . . .
C18 C 0.8483(4) 1.1411(3) 0.8796(3) 0.0465(9) Uani 1 1 d . . . . .
H18 H 0.819559 1.210128 0.891548 0.056 Uiso 1 1 calc R U . . .
C19 C 0.9597(4) 1.1335(3) 0.8304(3) 0.0515(10) Uani 1 1 d . . . . .
H19 H 1.006450 1.198784 0.806904 0.062 Uiso 1 1 calc R U . . .
C20 C 1.0037(4) 1.0344(3) 0.8149(3) 0.0484(10) Uani 1 1 d . . . . .
H20 H 1.081402 1.032730 0.782407 0.058 Uiso 1 1 calc R U . . .
C21 C 0.9368(4) 0.9362(3) 0.8459(3) 0.0431(8) Uani 1 1 d . . . . .
H21 H 0.966591 0.867320 0.835027 0.052 Uiso 1 1 calc R U . . .
C22 C 0.8248(3) 0.9438(3) 0.8933(2) 0.0373(8) Uani 1 1 d . . . . .
Cl1 Cl 0.58616(9) 0.01641(7) 0.28963(7) 0.0471(3) Uani 1 1 d . . . . .
N1 N 0.1654(3) 0.0593(2) 0.4638(2) 0.0377(7) Uani 1 1 d . . . . .
H1 H 0.096836 0.002312 0.433622 0.045 Uiso 1 1 calc R U . . .
N2 N 0.2822(3) 0.2125(2) 0.5625(2) 0.0366(6) Uani 1 1 d . . . . .
N3 N 0.5116(3) 0.4838(2) 0.7850(2) 0.0381(7) Uani 1 1 d D . . . .
H3N H 0.591(3) 0.470(3) 0.764(3) 0.072(13) Uiso 1 1 d D . . . .
N4 N 0.7368(3) 0.8630(2) 0.9329(2) 0.0385(7) Uani 1 1 d . . . . .
N5 N 0.6703(3) 1.0213(2) 0.9612(2) 0.0396(7) Uani 1 1 d . . . . .
H5A H 0.625404 1.071294 0.982650 0.048 Uiso 1 1 calc R U . . .
O1 O 0.0507(2) 0.13331(19) 0.57926(19) 0.0485(6) Uani 1 1 d . . . . .
O2 O 0.5474(2) 0.86049(19) 1.01344(19) 0.0493(6) Uani 1 1 d . . . . .
C23 C 0.8498(6) 0.4428(5) 0.8068(5) 0.0427(12) Uani 0.763(3) 1 d . U P A 1
C24 C 1.0037(6) 0.4436(6) 0.7931(4) 0.0448(12) Uani 0.763(3) 1 d . U P A 1
H24 H 0.996283 0.384894 0.736385 0.054 Uiso 0.763(3) 1 calc R U P A 1
C25 C 1.0494(13) 0.5587(10) 0.7495(6) 0.0384(15) Uani 0.763(3) 1 d . U P A 1
C26 C 1.1297(5) 0.6450(4) 0.8248(4) 0.0454(10) Uani 0.763(3) 1 d . U P A 1
H26 H 1.160868 0.633940 0.901547 0.054 Uiso 0.763(3) 1 calc R U P A 1
C27 C 1.1632(6) 0.7482(5) 0.7841(6) 0.0487(12) Uani 0.763(3) 1 d . U P A 1
H27 H 1.221131 0.807793 0.833366 0.058 Uiso 0.763(3) 1 calc R U P A 1
C28 C 1.1126(6) 0.7639(6) 0.6730(4) 0.0469(13) Uani 0.763(3) 1 d . U P A 1
H28 H 1.131267 0.835116 0.646072 0.056 Uiso 0.763(3) 1 calc R U P A 1
C29 C 1.0354(5) 0.6771(4) 0.6015(4) 0.0457(11) Uani 0.763(3) 1 d . U P A 1
H29 H 1.003683 0.688166 0.524722 0.055 Uiso 0.763(3) 1 calc R U P A 1
C30 C 1.0028(5) 0.5733(4) 0.6391(4) 0.0428(11) Uani 0.763(3) 1 d . U P A 1
H30 H 0.948896 0.513335 0.588886 0.051 Uiso 0.763(3) 1 calc R U P A 1
O3 O 0.7378(4) 0.4417(3) 0.7218(3) 0.0375(8) Uani 0.763(3) 1 d . U P A 1
O4 O 0.8411(3) 0.4468(3) 0.9046(3) 0.0522(10) Uani 0.763(3) 1 d . U P A 1
O5 O 1.1114(3) 0.4228(3) 0.8922(3) 0.0609(11) Uani 0.763(3) 1 d . U P A 1
H5O H 1.079560 0.433524 0.945452 0.091 Uiso 0.763(3) 1 calc R U P A 1
C23D C 0.815(2) 0.4278(18) 0.7341(15) 0.057(3) Uani 0.237(3) 1 d D U P A 2
C24D C 0.984(3) 0.443(2) 0.7447(16) 0.059(3) Uani 0.237(3) 1 d D U P A 2
H24D H 1.032136 0.396674 0.805624 0.070 Uiso 0.237(3) 1 calc R U P A 2
C25D C 1.058(5) 0.555(4) 0.776(2) 0.039(3) Uani 0.237(3) 1 d . U P A 2
C26D C 1.1424(15) 0.5837(15) 0.8848(14) 0.051(2) Uani 0.237(3) 1 d . U P A 2
H26D H 1.146039 0.531650 0.940369 0.061 Uiso 0.237(3) 1 calc R U P A 2
C27D C 1.2255(16) 0.6957(14) 0.9118(14) 0.052(2) Uani 0.237(3) 1 d . U P A 2
H27D H 1.281952 0.718618 0.985497 0.063 Uiso 0.237(3) 1 calc R U P A 2
C28D C 1.2204(19) 0.7640(18) 0.8316(16) 0.050(2) Uani 0.237(3) 1 d . U P A 2
H28D H 1.277798 0.835413 0.851536 0.060 Uiso 0.237(3) 1 calc R U P A 2
C29D C 1.138(2) 0.743(2) 0.718(2) 0.049(2) Uani 0.237(3) 1 d . U P A 2
H29D H 1.136193 0.797592 0.665412 0.058 Uiso 0.237(3) 1 calc R U P A 2
C30D C 1.0561(16) 0.6291(14) 0.6874(14) 0.045(2) Uani 0.237(3) 1 d . U P A 2
H30A H 0.950091 0.634456 0.647142 0.054 Uiso 0.237(3) 1 calc R U P A 2
H30B H 1.098364 0.594997 0.635591 0.054 Uiso 0.237(3) 1 calc R U P A 2
O3D O 0.7265(16) 0.4474(15) 0.6530(15) 0.103(5) Uani 0.237(3) 1 d D U P A 2
O4D O 0.8004(19) 0.4255(17) 0.8247(16) 0.084(4) Uani 0.237(3) 1 d D U P A 2
O5D O 0.9895(18) 0.3970(14) 0.6524(14) 0.113(4) Uani 0.237(3) 1 d D U P A 2
H5OD H 1.039748 0.344723 0.667389 0.170 Uiso 0.237(3) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.381(4) . ?
C1 C6 1.394(4) . ?
C1 Cl1 1.741(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
C3 N1 1.389(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.390(4) . ?
C4 N2 1.399(4) . ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.237(4) . ?
C7 N1 1.357(4) . ?
C7 N2 1.389(4) . ?
C8 N2 1.458(4) . ?
C8 C12 1.508(5) . ?
C8 C9 1.518(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.523(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N3 1.497(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N3 1.485(4) . ?
C11 C12 1.516(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.495(5) . ?
C13 N3 1.496(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.555(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N4 1.437(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O2 1.250(4) . ?
C16 N5 1.355(4) . ?
C16 N4 1.363(4) . ?
C17 C22 1.380(5) . ?
C17 C18 1.381(4) . ?
C17 N5 1.393(4) . ?
C18 C19 1.393(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.372(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(5) . ?
C21 H21 0.9500 . ?
C22 N4 1.394(4) . ?
N1 H1 0.8800 . ?
N3 H3N 0.907(19) . ?
N5 H5A 0.8800 . ?
C23 O3 1.265(7) . ?
C23 O4 1.277(7) . ?
C23 C24 1.516(8) . ?
C24 O5 1.414(5) . ?
C24 C25 1.566(13) . ?
C24 H24 1.0000 . ?
C25 C30 1.364(8) . ?
C25 C26 1.394(12) . ?
C26 C27 1.398(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.377(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.366(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(7) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
O5 H5O 0.8400 . ?
C23D O3D 1.168(16) . ?
C23D O4D 1.206(17) . ?
C23D C24D 1.55(3) . ?
C24D O5D 1.325(16) . ?
C24D C25D 1.44(5) . ?
C24D H24D 1.0000 . ?
C25D C26D 1.39(3) . ?
C25D C30D 1.45(4) . ?
C26D C27D 1.46(2) . ?
C26D H26D 0.9500 . ?
C27D C28D 1.32(2) . ?
C27D H27D 0.9500 . ?
C28D C29D 1.43(3) . ?
C28D H28D 0.9500 . ?
C29D C30D 1.48(3) . ?
C29D H29D 0.9500 . ?
C30D H30A 0.9900 . ?
C30D H30B 0.9900 . ?
O5D H5OD 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.3(3) . . ?
C2 C1 Cl1 118.1(3) . . ?
C6 C1 Cl1 119.6(2) . . ?
C3 C2 C1 116.6(3) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
C2 C3 N1 130.6(3) . . ?
C2 C3 C4 122.2(3) . . ?
N1 C3 C4 107.2(3) . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 N2 133.0(3) . . ?
C3 C4 N2 106.7(2) . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 N1 127.6(3) . . ?
O1 C7 N2 125.3(3) . . ?
N1 C7 N2 107.1(3) . . ?
N2 C8 C12 110.9(3) . . ?
N2 C8 C9 112.0(3) . . ?
C12 C8 C9 111.3(3) . . ?
N2 C8 H8 107.5 . . ?
C12 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C8 C9 C10 111.9(3) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 C9 109.8(3) . . ?
N3 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
N3 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N3 C11 C12 110.6(3) . . ?
N3 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C8 C12 C11 111.2(3) . . ?
C8 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C8 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 N3 113.1(3) . . ?
C14 C13 H13A 108.9 . . ?
N3 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
N3 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 108.0(3) . . ?
C13 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
C13 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
N4 C15 C14 112.5(3) . . ?
N4 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
N4 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
O2 C16 N5 128.0(3) . . ?
O2 C16 N4 124.8(3) . . ?
N5 C16 N4 107.1(3) . . ?
C22 C17 C18 121.2(3) . . ?
C22 C17 N5 106.8(3) . . ?
C18 C17 N5 132.0(3) . . ?
C17 C18 C19 116.9(3) . . ?
C17 C18 H18 121.6 . . ?
C19 C18 H18 121.6 . . ?
C20 C19 C18 121.8(3) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 116.7(3) . . ?
C22 C21 H21 121.7 . . ?
C20 C21 H21 121.7 . . ?
C17 C22 C21 122.0(3) . . ?
C17 C22 N4 106.9(3) . . ?
C21 C22 N4 131.1(3) . . ?
C7 N1 C3 110.0(2) . . ?
C7 N1 H1 125.0 . . ?
C3 N1 H1 125.0 . . ?
C7 N2 C4 108.8(3) . . ?
C7 N2 C8 122.3(3) . . ?
C4 N2 C8 128.6(2) . . ?
C11 N3 C13 110.0(3) . . ?
C11 N3 C10 110.6(2) . . ?
C13 N3 C10 113.7(3) . . ?
C11 N3 H3N 105(3) . . ?
C13 N3 H3N 109(3) . . ?
C10 N3 H3N 108(3) . . ?
C16 N4 C22 109.4(3) . . ?
C16 N4 C15 121.9(3) . . ?
C22 N4 C15 128.6(3) . . ?
C16 N5 C17 109.8(3) . . ?
C16 N5 H5A 125.1 . . ?
C17 N5 H5A 125.1 . . ?
O3 C23 O4 123.3(5) . . ?
O3 C23 C24 118.9(5) . . ?
O4 C23 C24 117.8(5) . . ?
O5 C24 C23 112.1(5) . . ?
O5 C24 C25 111.5(6) . . ?
C23 C24 C25 107.4(6) . . ?
O5 C24 H24 108.6 . . ?
C23 C24 H24 108.6 . . ?
C25 C24 H24 108.6 . . ?
C30 C25 C26 121.7(9) . . ?
C30 C25 C24 119.0(8) . . ?
C26 C25 C24 119.1(5) . . ?
C25 C26 C27 118.1(6) . . ?
C25 C26 H26 121.0 . . ?
C27 C26 H26 121.0 . . ?
C28 C27 C26 120.3(6) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 120.0(6) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 121.0(5) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C25 C30 C29 118.8(7) . . ?
C25 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C24 O5 H5O 109.5 . . ?
O3D C23D O4D 127(2) . . ?
O3D C23D C24D 120.9(18) . . ?
O4D C23D C24D 109.2(18) . . ?
O5D C24D C25D 119(2) . . ?
O5D C24D C23D 104.3(17) . . ?
C25D C24D C23D 113(2) . . ?
O5D C24D H24D 106.6 . . ?
C25D C24D H24D 106.6 . . ?
C23D C24D H24D 106.6 . . ?
C26D C25D C24D 120(3) . . ?
C26D C25D C30D 123(3) . . ?
C24D C25D C30D 117(2) . . ?
C25D C26D C27D 119(2) . . ?
C25D C26D H26D 120.7 . . ?
C27D C26D H26D 120.7 . . ?
C28D C27D C26D 118.6(17) . . ?
C28D C27D H27D 120.7 . . ?
C26D C27D H27D 120.7 . . ?
C27D C28D C29D 127(2) . . ?
C27D C28D H28D 116.4 . . ?
C29D C28D H28D 116.4 . . ?
C28D C29D C30D 116(2) . . ?
C28D C29D H29D 122.2 . . ?
C30D C29D H29D 122.2 . . ?
C25D C30D C29D 117(2) . . ?
C25D C30D H30A 108.0 . . ?
C29D C30D H30A 108.0 . . ?
C25D C30D H30B 108.0 . . ?
C29D C30D H30B 108.0 . . ?
H30A C30D H30B 107.3 . . ?
C24D O5D H5OD 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(4) . . . . ?
Cl1 C1 C2 C3 180.0(2) . . . . ?
C1 C2 C3 N1 -177.6(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
N1 C3 C4 C5 176.8(3) . . . . ?
C2 C3 C4 N2 179.6(3) . . . . ?
N1 C3 C4 N2 -2.0(3) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
N2 C4 C5 C6 179.9(3) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
Cl1 C1 C6 C5 179.9(2) . . . . ?
N2 C8 C9 C10 -177.2(2) . . . . ?
C12 C8 C9 C10 -52.4(4) . . . . ?
C8 C9 C10 N3 55.3(3) . . . . ?
N2 C8 C12 C11 178.0(2) . . . . ?
C9 C8 C12 C11 52.7(4) . . . . ?
N3 C11 C12 C8 -56.9(4) . . . . ?
N3 C13 C14 C15 -154.7(3) . . . . ?
C13 C14 C15 N4 -139.6(3) . . . . ?
C22 C17 C18 C19 0.4(5) . . . . ?
N5 C17 C18 C19 179.3(3) . . . . ?
C17 C18 C19 C20 -1.3(5) . . . . ?
C18 C19 C20 C21 1.3(5) . . . . ?
C19 C20 C21 C22 -0.3(5) . . . . ?
C18 C17 C22 C21 0.5(5) . . . . ?
N5 C17 C22 C21 -178.6(3) . . . . ?
C18 C17 C22 N4 180.0(3) . . . . ?
N5 C17 C22 N4 0.9(3) . . . . ?
C20 C21 C22 C17 -0.6(4) . . . . ?
C20 C21 C22 N4 -179.9(3) . . . . ?
O1 C7 N1 C3 -177.8(3) . . . . ?
N2 C7 N1 C3 2.2(3) . . . . ?
C2 C3 N1 C7 178.2(3) . . . . ?
C4 C3 N1 C7 -0.1(3) . . . . ?
O1 C7 N2 C4 176.5(3) . . . . ?
N1 C7 N2 C4 -3.4(3) . . . . ?
O1 C7 N2 C8 2.0(5) . . . . ?
N1 C7 N2 C8 -178.0(3) . . . . ?
C5 C4 N2 C7 -175.2(3) . . . . ?
C3 C4 N2 C7 3.4(3) . . . . ?
C5 C4 N2 C8 -1.0(5) . . . . ?
C3 C4 N2 C8 177.5(3) . . . . ?
C12 C8 N2 C7 103.7(3) . . . . ?
C9 C8 N2 C7 -131.3(3) . . . . ?
C12 C8 N2 C4 -69.7(4) . . . . ?
C9 C8 N2 C4 55.3(4) . . . . ?
C12 C11 N3 C13 -173.1(3) . . . . ?
C12 C11 N3 C10 60.5(3) . . . . ?
C14 C13 N3 C11 172.7(3) . . . . ?
C14 C13 N3 C10 -62.6(4) . . . . ?
C9 C10 N3 C11 -59.3(3) . . . . ?
C9 C10 N3 C13 176.3(3) . . . . ?
O2 C16 N4 C22 179.5(3) . . . . ?
N5 C16 N4 C22 -1.3(3) . . . . ?
O2 C16 N4 C15 -3.0(5) . . . . ?
N5 C16 N4 C15 176.3(3) . . . . ?
C17 C22 N4 C16 0.2(3) . . . . ?
C21 C22 N4 C16 179.7(3) . . . . ?
C17 C22 N4 C15 -177.1(3) . . . . ?
C21 C22 N4 C15 2.3(5) . . . . ?
C14 C15 N4 C16 90.8(4) . . . . ?
C14 C15 N4 C22 -92.1(4) . . . . ?
O2 C16 N5 C17 -178.9(3) . . . . ?
N4 C16 N5 C17 1.9(3) . . . . ?
C22 C17 N5 C16 -1.7(3) . . . . ?
C18 C17 N5 C16 179.3(3) . . . . ?
O3 C23 C24 O5 -168.3(5) . . . . ?
O4 C23 C24 O5 13.9(8) . . . . ?
O3 C23 C24 C25 68.9(7) . . . . ?
O4 C23 C24 C25 -108.9(6) . . . . ?
O5 C24 C25 C30 151.2(8) . . . . ?
C23 C24 C25 C30 -85.6(10) . . . . ?
O5 C24 C25 C26 -32.1(11) . . . . ?
C23 C24 C25 C26 91.1(9) . . . . ?
C30 C25 C26 C27 -0.5(13) . . . . ?
C24 C25 C26 C27 -177.1(7) . . . . ?
C25 C26 C27 C28 2.4(9) . . . . ?
C26 C27 C28 C29 -3.1(8) . . . . ?
C27 C28 C29 C30 2.0(7) . . . . ?
C26 C25 C30 C29 -0.6(13) . . . . ?
C24 C25 C30 C29 176.0(6) . . . . ?
C28 C29 C30 C25 -0.1(9) . . . . ?
O3D C23D C24D O5D -46(3) . . . . ?
O4D C23D C24D O5D 153(2) . . . . ?
O3D C23D C24D C25D 84(3) . . . . ?
O4D C23D C24D C25D -76(3) . . . . ?
O5D C24D C25D C26D -137(3) . . . . ?
C23D C24D C25D C26D 100(3) . . . . ?
O5D C24D C25D C30D 35(4) . . . . ?
C23D C24D C25D C30D -88(3) . . . . ?
C24D C25D C26D C27D 175(2) . . . . ?
C30D C25D C26D C27D 4(4) . . . . ?
C25D C26D C27D C28D -2(3) . . . . ?
C26D C27D C28D C29D 2(3) . . . . ?
C27D C28D C29D C30D -3(3) . . . . ?
C26D C25D C30D C29D -5(4) . . . . ?
C24D C25D C30D C29D -177(2) . . . . ?
C28D C29D C30D C25D 5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.88 1.98 2.823(3) 159.8 2_556 yes
N5 H5A O2 0.88 1.95 2.775(4) 154.8 2_677 yes
O5^a H5O^a O4^a 0.84 2.28 2.927(5) 134.3 2_767 yes
N3 H3N O3^a 0.907(19) 1.711(19) 2.618(4) 179(4) . yes
N3 H3N O4^a 0.907(19) 2.55(3) 3.126(4) 122(3) . yes
O5^a H5O^a O4^a 0.84 2.18 2.665(4) 116.2 . yes

_refine_diff_density_max         0.505
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.063


_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB546_0m
_database_code_depnum_ccdc_archive 'CCDC 2240375'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-09-26 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Domperidone orotate'
_chemical_name_common            'Domperidone orotate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 Cl N5 O2 1+, C5 H3 N2 O4 1-'
_chemical_formula_sum            'C27 H28 Cl N7 O6'
_chemical_formula_weight         582.01

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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5379(4)
_cell_length_b                   11.3926(6)
_cell_length_c                   15.8690(8)
_cell_angle_alpha                99.679(2)
_cell_angle_beta                 102.801(2)
_cell_angle_gamma                91.935(2)
_cell_volume                     1306.40(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3380
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      21.02

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4624
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            25326
_diffrn_reflns_av_unetI/netI     0.1273
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.676
_diffrn_reflns_theta_max         28.352
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6485
_reflns_number_gt                2721
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6485
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1688
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1504(4) 0.4655(3) 0.06593(19) 0.0424(7) Uani 1 1 d . . . . .
C2 C -0.1939(4) 0.3719(3) -0.00559(17) 0.0412(7) Uani 1 1 d . . . . .
H2 H -0.298657 0.369125 -0.049962 0.049 Uiso 1 1 calc R U . . .
C3 C -0.0736(4) 0.2836(2) -0.00720(17) 0.0374(7) Uani 1 1 d . . . . .
C4 C 0.0826(4) 0.2853(2) 0.06015(17) 0.0360(7) Uani 1 1 d . . . . .
C5 C 0.1258(4) 0.3799(2) 0.12981(17) 0.0419(7) Uani 1 1 d . . . . .
H5A H 0.230878 0.383168 0.174102 0.050 Uiso 1 1 calc R U . . .
C6 C 0.0065(4) 0.4699(2) 0.13117(17) 0.0419(7) Uani 1 1 d . . . . .
H6A H 0.032799 0.534834 0.177194 0.050 Uiso 1 1 calc R U . . .
C7 C 0.0763(4) 0.1206(3) -0.04352(19) 0.0447(8) Uani 1 1 d . . . . .
C8 C 0.3423(4) 0.1477(2) 0.08574(17) 0.0406(7) Uani 1 1 d . . . . .
H8 H 0.365872 0.070808 0.053455 0.049 Uiso 1 1 calc R U . . .
C9 C 0.3297(4) 0.1285(3) 0.17729(17) 0.0442(7) Uani 1 1 d . . . . .
H9A H 0.285788 0.199082 0.207224 0.053 Uiso 1 1 calc R U . . .
H9B H 0.241812 0.061862 0.171628 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5112(4) 0.1038(2) 0.23234(18) 0.0448(8) Uani 1 1 d . . . . .
H10A H 0.498321 0.097755 0.290958 0.054 Uiso 1 1 calc R U . . .
H10B H 0.549304 0.028424 0.206339 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6766(4) 0.2095(2) 0.14744(16) 0.0403(7) Uani 1 1 d . . . . .
H11A H 0.716075 0.134533 0.121478 0.048 Uiso 1 1 calc R U . . .
H11B H 0.770406 0.271941 0.151489 0.048 Uiso 1 1 calc R U . . .
C12 C 0.5008(4) 0.2361(3) 0.08954(16) 0.0414(7) Uani 1 1 d . . . . .
H12A H 0.517942 0.234468 0.030568 0.050 Uiso 1 1 calc R U . . .
H12B H 0.470799 0.315865 0.111436 0.050 Uiso 1 1 calc R U . . .
C13 C 0.8293(4) 0.1887(2) 0.29922(18) 0.0425(7) Uani 1 1 d . . . . .
H13A H 0.901844 0.136181 0.268284 0.051 Uiso 1 1 calc R U . . .
H13B H 0.805338 0.152596 0.347119 0.051 Uiso 1 1 calc R U . . .
C14 C 0.9359(4) 0.3088(2) 0.33623(17) 0.0426(7) Uani 1 1 d . . . . .
H14A H 0.935610 0.352382 0.288685 0.051 Uiso 1 1 calc R U . . .
H14B H 0.875306 0.354730 0.377309 0.051 Uiso 1 1 calc R U . . .
C15 C 1.1320(4) 0.2974(2) 0.38271(17) 0.0415(7) Uani 1 1 d . . . . .
H15A H 1.199770 0.267867 0.339210 0.050 Uiso 1 1 calc R U . . .
H15B H 1.186829 0.375950 0.412503 0.050 Uiso 1 1 calc R U . . .
C16 C 1.2070(4) 0.1052(2) 0.43270(19) 0.0389(7) Uani 1 1 d . . . . .
C17 C 1.1626(4) 0.1470(2) 0.57070(17) 0.0381(7) Uani 1 1 d . . . . .
C18 C 1.1498(4) 0.1461(3) 0.65553(19) 0.0500(8) Uani 1 1 d . . . . .
H18 H 1.178268 0.080352 0.682231 0.060 Uiso 1 1 calc R U . . .
C19 C 1.0925(4) 0.2477(3) 0.6992(2) 0.0561(9) Uani 1 1 d . . . . .
H19 H 1.080874 0.249739 0.756555 0.067 Uiso 1 1 calc R U . . .
C20 C 1.0519(4) 0.3461(3) 0.6607(2) 0.0536(9) Uani 1 1 d . . . . .
H20 H 1.016486 0.413564 0.692797 0.064 Uiso 1 1 calc R U . . .
C21 C 1.0631(4) 0.3460(3) 0.57498(19) 0.0481(8) Uani 1 1 d . . . . .
H21 H 1.033365 0.411526 0.548172 0.058 Uiso 1 1 calc R U . . .
C22 C 1.1199(4) 0.2452(2) 0.53091(16) 0.0344(7) Uani 1 1 d . . . . .
Cl1 Cl -0.29487(12) 0.58001(7) 0.07345(5) 0.0615(3) Uani 1 1 d . . . . .
N1 N -0.0742(4) 0.1818(2) -0.06868(18) 0.0472(7) Uani 1 1 d . . . . .
H1N H -0.150(4) 0.167(3) -0.1154(19) 0.052(10) Uiso 1 1 d . . . . .
N2 N 0.1714(3) 0.18327(19) 0.03716(14) 0.0399(6) Uani 1 1 d . . . . .
N3 N 0.6525(3) 0.2018(2) 0.23774(13) 0.0337(6) Uani 1 1 d . . . . .
H3N H 0.601(4) 0.273(3) 0.2563(17) 0.055(9) Uiso 1 1 d . . . . .
N4 N 1.1481(3) 0.21817(18) 0.44630(13) 0.0372(6) Uani 1 1 d . . . . .
N5 N 1.2155(3) 0.0614(2) 0.50881(15) 0.0433(7) Uani 1 1 d . . . . .
H5N H 1.255(6) -0.012(4) 0.510(2) 0.116(15) Uiso 1 1 d . . . . .
O1 O 0.1195(3) 0.02919(19) -0.08400(13) 0.0653(7) Uani 1 1 d . . . . .
O2 O 1.2417(3) 0.05405(16) 0.36390(12) 0.0499(6) Uani 1 1 d . . . . .
C23 C 0.5304(4) 0.4750(2) 0.3552(2) 0.0383(7) Uani 1 1 d . . . . .
C24 C 0.4640(4) 0.5993(2) 0.35197(17) 0.0332(7) Uani 1 1 d . . . . .
C25 C 0.4409(4) 0.6474(2) 0.27930(17) 0.0362(7) Uani 1 1 d . . . . .
H25 H 0.460494 0.603013 0.227798 0.043 Uiso 1 1 calc R U . . .
C26 C 0.3862(4) 0.7668(2) 0.28027(18) 0.0377(7) Uani 1 1 d . . . . .
C27 C 0.3781(4) 0.7753(2) 0.43522(18) 0.0373(7) Uani 1 1 d . . . . .
O3 O 0.5164(3) 0.40946(17) 0.28169(13) 0.0603(6) Uani 1 1 d . . . . .
O4 O 0.5951(3) 0.45059(17) 0.42789(13) 0.0582(6) Uani 1 1 d . . . . .
O5 O 0.3613(3) 0.81876(17) 0.21700(12) 0.0514(6) Uani 1 1 d . . . . .
O6 O 0.3485(3) 0.83138(16) 0.50323(12) 0.0485(6) Uani 1 1 d . . . . .
N6 N 0.4333(3) 0.66168(19) 0.42817(15) 0.0357(6) Uani 1 1 d . . . . .
H6N H 0.445(4) 0.630(3) 0.4769(19) 0.058(10) Uiso 1 1 d . . . . .
N7 N 0.3609(3) 0.8224(2) 0.36002(15) 0.0380(6) Uani 1 1 d . . . . .
H7N H 0.325(4) 0.885(2) 0.3612(15) 0.027(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.382(4) . ?
C1 C2 1.392(4) . ?
C1 Cl1 1.733(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 N1 1.384(3) . ?
C3 C4 1.401(4) . ?
C4 C5 1.381(3) . ?
C4 N2 1.396(3) . ?
C5 C6 1.387(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 O1 1.222(3) . ?
C7 N1 1.371(4) . ?
C7 N2 1.383(3) . ?
C8 N2 1.456(3) . ?
C8 C12 1.520(4) . ?
C8 C9 1.527(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.514(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N3 1.495(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.500(3) . ?
C11 C12 1.508(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.495(3) . ?
C13 C14 1.519(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.519(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N4 1.452(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.234(3) . ?
C16 N5 1.372(3) . ?
C16 N4 1.373(3) . ?
C17 C18 1.372(4) . ?
C17 C22 1.388(4) . ?
C17 N5 1.397(3) . ?
C18 C19 1.379(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(4) . ?
C21 H21 0.9300 . ?
C22 N4 1.391(3) . ?
N1 H1N 0.82(3) . ?
N3 H3N 0.94(3) . ?
N5 H5N 0.90(4) . ?
C23 O4 1.231(3) . ?
C23 O3 1.255(3) . ?
C23 C24 1.522(4) . ?
C24 C25 1.338(3) . ?
C24 N6 1.366(3) . ?
C25 C26 1.434(4) . ?
C25 H25 0.9300 . ?
C26 O5 1.231(3) . ?
C26 N7 1.373(3) . ?
C27 O6 1.228(3) . ?
C27 N6 1.367(3) . ?
C27 N7 1.371(3) . ?
N6 H6N 0.90(3) . ?
N7 H7N 0.77(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.5(2) . . ?
C6 C1 Cl1 119.0(2) . . ?
C2 C1 Cl1 119.5(2) . . ?
C3 C2 C1 116.5(3) . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
C2 C3 N1 130.9(3) . . ?
C2 C3 C4 122.4(3) . . ?
N1 C3 C4 106.7(3) . . ?
C5 C4 N2 132.6(3) . . ?
C5 C4 C3 120.4(2) . . ?
N2 C4 C3 106.9(2) . . ?
C4 C5 C6 117.4(3) . . ?
C4 C5 H5A 121.3 . . ?
C6 C5 H5A 121.3 . . ?
C1 C6 C5 121.7(3) . . ?
C1 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
O1 C7 N1 127.2(3) . . ?
O1 C7 N2 126.4(3) . . ?
N1 C7 N2 106.3(3) . . ?
N2 C8 C12 111.2(2) . . ?
N2 C8 C9 111.7(2) . . ?
C12 C8 C9 111.7(2) . . ?
N2 C8 H8 107.3 . . ?
C12 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C10 C9 C8 112.6(2) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N3 C10 C9 110.3(2) . . ?
N3 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N3 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N3 C11 C12 110.9(2) . . ?
N3 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C8 112.8(2) . . ?
C11 C12 H12A 109.0 . . ?
C8 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C8 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N3 C13 C14 111.3(2) . . ?
N3 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 112.9(2) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
N4 C15 C14 113.3(2) . . ?
N4 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
N4 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
O2 C16 N5 127.6(2) . . ?
O2 C16 N4 125.5(3) . . ?
N5 C16 N4 106.9(2) . . ?
C18 C17 C22 121.6(2) . . ?
C18 C17 N5 131.7(3) . . ?
C22 C17 N5 106.7(2) . . ?
C17 C18 C19 116.7(3) . . ?
C17 C18 H18 121.7 . . ?
C19 C18 H18 121.7 . . ?
C20 C19 C18 122.1(3) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 117.4(3) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
C21 C22 C17 121.3(2) . . ?
C21 C22 N4 131.3(2) . . ?
C17 C22 N4 107.4(2) . . ?
C7 N1 C3 110.6(3) . . ?
C7 N1 H1N 127(2) . . ?
C3 N1 H1N 122(2) . . ?
C7 N2 C4 109.4(2) . . ?
C7 N2 C8 123.3(2) . . ?
C4 N2 C8 127.2(2) . . ?
C10 N3 C13 112.5(2) . . ?
C10 N3 C11 109.8(2) . . ?
C13 N3 C11 112.0(2) . . ?
C10 N3 H3N 105.2(17) . . ?
C13 N3 H3N 111.7(17) . . ?
C11 N3 H3N 105.2(16) . . ?
C16 N4 C22 109.4(2) . . ?
C16 N4 C15 123.8(2) . . ?
C22 N4 C15 126.7(2) . . ?
C16 N5 C17 109.6(2) . . ?
C16 N5 H5N 117(2) . . ?
C17 N5 H5N 134(2) . . ?
O4 C23 O3 127.2(2) . . ?
O4 C23 C24 117.6(2) . . ?
O3 C23 C24 115.1(3) . . ?
C25 C24 N6 121.0(2) . . ?
C25 C24 C23 122.3(2) . . ?
N6 C24 C23 116.7(2) . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
O5 C26 N7 120.6(2) . . ?
O5 C26 C25 125.3(2) . . ?
N7 C26 C25 114.1(3) . . ?
O6 C27 N6 123.1(2) . . ?
O6 C27 N7 122.5(2) . . ?
N6 C27 N7 114.3(2) . . ?
C24 N6 C27 122.8(2) . . ?
C24 N6 H6N 122.1(18) . . ?
C27 N6 H6N 115.0(18) . . ?
C27 N7 C26 127.3(3) . . ?
C27 N7 H7N 116.6(18) . . ?
C26 N7 H7N 115.9(18) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.7(4) . . . . ?
Cl1 C1 C2 C3 -179.7(2) . . . . ?
C1 C2 C3 N1 -178.3(3) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C2 C3 C4 C5 -2.8(4) . . . . ?
N1 C3 C4 C5 177.0(2) . . . . ?
C2 C3 C4 N2 179.9(2) . . . . ?
N1 C3 C4 N2 -0.3(3) . . . . ?
N2 C4 C5 C6 178.3(3) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
C2 C1 C6 C5 -1.7(4) . . . . ?
Cl1 C1 C6 C5 178.7(2) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
N2 C8 C9 C10 -174.1(2) . . . . ?
C12 C8 C9 C10 -48.8(3) . . . . ?
C8 C9 C10 N3 55.4(3) . . . . ?
N3 C11 C12 C8 -54.4(3) . . . . ?
N2 C8 C12 C11 173.8(2) . . . . ?
C9 C8 C12 C11 48.2(3) . . . . ?
N3 C13 C14 C15 -167.5(2) . . . . ?
C13 C14 C15 N4 -49.9(3) . . . . ?
C22 C17 C18 C19 0.0(4) . . . . ?
N5 C17 C18 C19 179.8(3) . . . . ?
C17 C18 C19 C20 -0.8(5) . . . . ?
C18 C19 C20 C21 1.5(5) . . . . ?
C19 C20 C21 C22 -1.4(5) . . . . ?
C20 C21 C22 C17 0.6(4) . . . . ?
C20 C21 C22 N4 -178.7(3) . . . . ?
C18 C17 C22 C21 0.1(4) . . . . ?
N5 C17 C22 C21 -179.8(3) . . . . ?
C18 C17 C22 N4 179.6(3) . . . . ?
N5 C17 C22 N4 -0.3(3) . . . . ?
O1 C7 N1 C3 -177.8(3) . . . . ?
N2 C7 N1 C3 1.9(3) . . . . ?
C2 C3 N1 C7 178.8(3) . . . . ?
C4 C3 N1 C7 -1.0(3) . . . . ?
O1 C7 N2 C4 177.7(3) . . . . ?
N1 C7 N2 C4 -2.1(3) . . . . ?
O1 C7 N2 C8 0.6(5) . . . . ?
N1 C7 N2 C8 -179.2(2) . . . . ?
C5 C4 N2 C7 -175.3(3) . . . . ?
C3 C4 N2 C7 1.5(3) . . . . ?
C5 C4 N2 C8 1.6(5) . . . . ?
C3 C4 N2 C8 178.4(2) . . . . ?
C12 C8 N2 C7 111.8(3) . . . . ?
C9 C8 N2 C7 -122.6(3) . . . . ?
C12 C8 N2 C4 -64.8(3) . . . . ?
C9 C8 N2 C4 60.9(3) . . . . ?
C9 C10 N3 C13 173.8(2) . . . . ?
C9 C10 N3 C11 -60.7(3) . . . . ?
C14 C13 N3 C10 -153.8(2) . . . . ?
C14 C13 N3 C11 81.9(3) . . . . ?
C12 C11 N3 C10 60.4(3) . . . . ?
C12 C11 N3 C13 -173.8(2) . . . . ?
O2 C16 N4 C22 178.9(3) . . . . ?
N5 C16 N4 C22 0.1(3) . . . . ?
O2 C16 N4 C15 -5.0(4) . . . . ?
N5 C16 N4 C15 176.1(2) . . . . ?
C21 C22 N4 C16 179.5(3) . . . . ?
C17 C22 N4 C16 0.1(3) . . . . ?
C21 C22 N4 C15 3.6(5) . . . . ?
C17 C22 N4 C15 -175.8(2) . . . . ?
C14 C15 N4 C16 105.5(3) . . . . ?
C14 C15 N4 C22 -79.2(3) . . . . ?
O2 C16 N5 C17 -179.1(3) . . . . ?
N4 C16 N5 C17 -0.3(3) . . . . ?
C18 C17 N5 C16 -179.5(3) . . . . ?
C22 C17 N5 C16 0.3(3) . . . . ?
O4 C23 C24 C25 160.4(3) . . . . ?
O3 C23 C24 C25 -17.9(4) . . . . ?
O4 C23 C24 N6 -17.8(4) . . . . ?
O3 C23 C24 N6 163.9(2) . . . . ?
N6 C24 C25 C26 1.0(4) . . . . ?
C23 C24 C25 C26 -177.1(3) . . . . ?
C24 C25 C26 O5 -179.9(3) . . . . ?
C24 C25 C26 N7 -0.3(4) . . . . ?
C25 C24 N6 C27 0.0(4) . . . . ?
C23 C24 N6 C27 178.2(2) . . . . ?
O6 C27 N6 C24 179.2(3) . . . . ?
N7 C27 N6 C24 -1.7(4) . . . . ?
O6 C27 N7 C26 -178.3(3) . . . . ?
N6 C27 N7 C26 2.6(4) . . . . ?
O5 C26 N7 C27 178.0(3) . . . . ?
C25 C26 N7 C27 -1.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O5 0.82(3) 2.03(3) 2.821(4) 162(3) 2_565 yes
N5 H5N O6 0.90(4) 1.94(4) 2.832(3) 175(4) 1_645 yes
N6 H6N O4 0.90(3) 1.97(3) 2.843(3) 166(3) 2_666 yes
N7 H7N O2 0.77(2) 2.05(3) 2.811(3) 177(3) 1_465 yes
N3 H3N O3 0.94(3) 1.72(3) 2.658(3) 174(2) . yes

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB541_0m
_database_code_depnum_ccdc_archive 'CCDC 2240374'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-09-26 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Domperidone salicylate hydrate'
_chemical_name_common            'Domperidone salicylate hydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C22 H25 Cl N5 O2), 2(C7 H5 O3), 5(H2 O)'
_chemical_formula_sum            'C58 H70 Cl2 N10 O15'
_chemical_formula_weight         1218.14

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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4744(2)
_cell_length_b                   10.1384(2)
_cell_length_c                   21.5088(5)
_cell_angle_alpha                102.0057(7)
_cell_angle_beta                 94.2351(8)
_cell_angle_gamma                104.6243(9)
_cell_volume                     1528.79(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8673
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.6

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             642
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6849
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            34667
_diffrn_reflns_av_unetI/netI     0.1624
_diffrn_reflns_av_R_equivalents  0.1197
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.136
_diffrn_reflns_theta_max         30.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9336
_reflns_number_gt                4776
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0760P)²+0.0150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9336
_refine_ls_number_parameters     410
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1703
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1751
_refine_ls_wR_factor_gt          0.1423
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2761(3) -0.0964(2) 0.50708(9) 0.0393(4) Uani 1 1 d . . . . .
C2 C 0.2255(3) -0.04858(19) 0.45455(8) 0.0377(4) Uani 1 1 d . . . . .
H2 H 0.205324 -0.104464 0.413118 0.045 Uiso 1 1 calc R U . . .
C3 C 0.2065(3) 0.08544(19) 0.46642(8) 0.0341(4) Uani 1 1 d . . . . .
C4 C 0.2361(3) 0.17048(19) 0.52891(8) 0.0341(4) Uani 1 1 d . . . . .
C5 C 0.2907(3) 0.1227(2) 0.58058(8) 0.0424(5) Uani 1 1 d . . . . .
H5 H 0.314755 0.179562 0.621884 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3089(3) -0.0134(2) 0.56921(9) 0.0441(5) Uani 1 1 d . . . . .
H6 H 0.343232 -0.048993 0.603383 0.053 Uiso 1 1 calc R U . . .
C7 C 0.1564(3) 0.29293(19) 0.45829(8) 0.0353(4) Uani 1 1 d . . . . .
C8 C 0.2203(3) 0.42476(19) 0.57180(7) 0.0356(4) Uani 1 1 d . . . . .
H8 H 0.163399 0.485481 0.551790 0.043 Uiso 1 1 calc R U . . .
C9 C 0.4228(3) 0.5046(2) 0.59520(8) 0.0424(5) Uani 1 1 d . . . . .
H9A H 0.483305 0.448344 0.616152 0.051 Uiso 1 1 calc R U . . .
H9B H 0.486587 0.522681 0.558904 0.051 Uiso 1 1 calc R U . . .
C10 C 0.4368(3) 0.6424(2) 0.64183(8) 0.0461(5) Uani 1 1 d . . . . .
H10A H 0.567045 0.689664 0.657727 0.055 Uiso 1 1 calc R U . . .
H10B H 0.387352 0.702133 0.619532 0.055 Uiso 1 1 calc R U . . .
C11 C 0.1335(3) 0.5386(2) 0.67477(8) 0.0408(5) Uani 1 1 d . . . . .
H11A H 0.069882 0.592680 0.653474 0.049 Uiso 1 1 calc R U . . .
H11B H 0.071737 0.521470 0.711579 0.049 Uiso 1 1 calc R U . . .
C12 C 0.1191(3) 0.3997(2) 0.62903(9) 0.0441(5) Uani 1 1 d . . . . .
H12A H -0.011081 0.350195 0.614316 0.053 Uiso 1 1 calc R U . . .
H12B H 0.174132 0.342159 0.651033 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3454(3) 0.7605(2) 0.74101(8) 0.0430(5) Uani 1 1 d . . . . .
H13A H 0.272400 0.809255 0.719914 0.052 Uiso 1 1 calc R U . . .
H13B H 0.474263 0.816870 0.749108 0.052 Uiso 1 1 calc R U . . .
C14 C 0.2764(3) 0.7463(2) 0.80426(8) 0.0457(5) Uani 1 1 d . . . . .
H14A H 0.321151 0.675560 0.819780 0.055 Uiso 1 1 calc R U . . .
H14B H 0.141132 0.716944 0.798467 0.055 Uiso 1 1 calc R U . . .
C15 C 0.3472(4) 0.8868(2) 0.85303(8) 0.0487(6) Uani 1 1 d . . . . .
H15A H 0.481665 0.920013 0.855266 0.058 Uiso 1 1 calc R U . . .
H15B H 0.293348 0.954943 0.838901 0.058 Uiso 1 1 calc R U . . .
C16 C 0.1551(3) 0.9177(2) 0.94229(9) 0.0483(6) Uani 1 1 d . . . . .
C17 C 0.2993(3) 0.8322(2) 1.01427(9) 0.0452(5) Uani 1 1 d . . . . .
C18 C 0.3554(4) 0.7853(3) 1.06622(11) 0.0591(7) Uani 1 1 d . . . . .
H18 H 0.294985 0.791713 1.102546 0.071 Uiso 1 1 calc R U . . .
C19 C 0.5038(5) 0.7290(4) 1.06216(13) 0.0795(10) Uani 1 1 d . . . . .
H19 H 0.544355 0.696144 1.096379 0.095 Uiso 1 1 calc R U . . .
C20 C 0.5953(5) 0.7199(4) 1.00809(14) 0.0838(10) Uani 1 1 d . . . . .
H20 H 0.696860 0.682599 1.007186 0.101 Uiso 1 1 calc R U . . .
C21 C 0.5381(4) 0.7654(3) 0.95558(12) 0.0647(7) Uani 1 1 d . . . . .
H21 H 0.597757 0.757849 0.919089 0.078 Uiso 1 1 calc R U . . .
C22 C 0.3901(3) 0.8218(2) 0.95962(9) 0.0449(5) Uani 1 1 d . . . . .
Cl1 Cl 0.29848(9) -0.26696(6) 0.49403(3) 0.05216(16) Uani 1 1 d . . . . .
N1 N 0.1604(3) 0.16206(17) 0.42498(7) 0.0385(4) Uani 1 1 d . . . . .
H1N H 0.143(3) 0.134(2) 0.3831(10) 0.056(7) Uiso 1 1 d . . . . .
N2 N 0.2030(2) 0.29715(16) 0.52256(6) 0.0355(4) Uani 1 1 d . . . . .
N3 N 0.3324(2) 0.62152(17) 0.69718(6) 0.0337(3) Uani 1 1 d . . . . .
H3N H 0.392(3) 0.574(2) 0.7217(8) 0.031(5) Uiso 1 1 d . . . . .
N4 N 0.2996(3) 0.87623(19) 0.91650(7) 0.0454(4) Uani 1 1 d . . . . .
N5 N 0.1558(3) 0.8903(2) 1.00203(7) 0.0514(5) Uani 1 1 d . . . . .
H5N H 0.095(4) 0.919(3) 1.0295(12) 0.074(9) Uiso 1 1 d . . . . .
O1 O 0.1220(2) 0.38667(15) 0.43593(6) 0.0471(4) Uani 1 1 d . . . . .
O2 O 0.0452(3) 0.9694(2) 0.91615(6) 0.0664(6) Uani 1 1 d . . . . .
C23 C 0.6230(4) 0.4466(3) 0.76495(11) 0.0573(6) Uani 1 1 d . . . . .
C24 C 0.7856(2) 0.43359(17) 0.80655(6) 0.0470(5) Uani 1 1 d G . . . .
C25 C 0.8756(3) 0.33174(18) 0.78497(7) 0.0683(8) Uani 1 1 d G . . . .
C26 C 1.0300(3) 0.3236(2) 0.82263(11) 0.0962(12) Uani 1 1 d G . . . .
H26 H 1.090220 0.255435 0.808190 0.115 Uiso 1 1 calc R U . . .
C27 C 1.0944(3) 0.4173(3) 0.88185(10) 0.0972(11) Uani 1 1 d G . . . .
H27 H 1.197637 0.411838 0.907046 0.117 Uiso 1 1 calc R U . . .
C28 C 1.0043(3) 0.5192(2) 0.90343(7) 0.0790(9) Uani 1 1 d G . . . .
H28 H 1.047394 0.581847 0.943058 0.095 Uiso 1 1 calc R U . . .
C29 C 0.8500(3) 0.52730(15) 0.86578(7) 0.0586(6) Uani 1 1 d G . . . .
H29 H 0.789731 0.595454 0.880213 0.070 Uiso 1 1 calc R U . . .
O3 O 0.5737(3) 0.5564(2) 0.77886(9) 0.0744(6) Uani 1 1 d . . . . .
O4 O 0.5494(4) 0.3458(2) 0.71766(9) 0.0954(8) Uani 1 1 d . . . . .
O5 O 0.8143(5) 0.2377(3) 0.72809(11) 0.0995(9) Uani 1 1 d D . . . .
H5O H 0.696(4) 0.222(5) 0.738(2) 0.18(2) Uiso 1 1 d D . . . .
O1W O -0.1931(4) 0.8333(3) 0.80221(10) 0.0949(8) Uani 1 1 d D . . . .
H1W H -0.117(5) 0.888(4) 0.8350(14) 0.142 Uiso 1 1 d D U . . .
H2W H -0.246(6) 0.746(2) 0.803(2) 0.142 Uiso 1 1 d D U . . .
O2W O -0.0948(5) 0.9689(3) 0.70733(9) 0.1240(12) Uani 1 1 d D . . . .
H3W H -0.114(8) 0.918(4) 0.7365(18) 0.186 Uiso 1 1 d D U . . .
H4W H -0.091(8) 1.057(3) 0.720(2) 0.186 Uiso 1 1 d D U . . .
O3W O 0.3145(10) 0.0826(6) 0.7457(2) 0.117(2) Uani 0.5 1 d D . P . .
H5W H 0.354(13) 0.105(9) 0.7860(13) 0.176 Uiso 0.5 1 d D U P . .
H6W H 0.379(12) 0.149(7) 0.729(3) 0.176 Uiso 0.5 1 d D U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(3) . ?
C1 C6 1.390(3) . ?
C1 Cl1 1.746(2) . ?
C2 C3 1.375(2) . ?
C2 H2 0.9300 . ?
C3 N1 1.376(2) . ?
C3 C4 1.406(2) . ?
C4 C5 1.376(3) . ?
C4 N2 1.399(2) . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.223(2) . ?
C7 N1 1.379(2) . ?
C7 N2 1.390(2) . ?
C8 N2 1.4621(19) . ?
C8 C9 1.516(3) . ?
C8 C12 1.524(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.515(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N3 1.493(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.498(3) . ?
C11 C12 1.514(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.499(2) . ?
C13 C14 1.512(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.525(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N4 1.454(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.240(3) . ?
C16 N4 1.368(2) . ?
C16 N5 1.370(3) . ?
C17 C18 1.379(3) . ?
C17 N5 1.382(3) . ?
C17 C22 1.398(3) . ?
C18 C19 1.370(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(3) . ?
C21 H21 0.9300 . ?
C22 N4 1.390(3) . ?
N1 H1N 0.87(2) . ?
N3 H3N 0.95(2) . ?
N5 H5N 0.82(2) . ?
C23 O3 1.245(3) . ?
C23 O4 1.258(3) . ?
C23 C24 1.505(3) . ?
C24 C25 1.3900 . ?
C24 C29 1.3900 . ?
C25 O5 1.352(3) . ?
C25 C26 1.3900 . ?
C26 C27 1.3900 . ?
C26 H26 0.9300 . ?
C27 C28 1.3900 . ?
C27 H27 0.9300 . ?
C28 C29 1.3900 . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
O5 H5O 0.902(19) . ?
O1W H1W 0.864(19) . ?
O1W H2W 0.884(19) . ?
O2W H3W 0.891(19) . ?
O2W H4W 0.871(19) . ?
O3W H5W 0.86(2) . ?
O3W H6W 0.87(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.18(18) . . ?
C2 C1 Cl1 118.23(14) . . ?
C6 C1 Cl1 119.59(17) . . ?
C3 C2 C1 116.90(15) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 N1 130.57(15) . . ?
C2 C3 C4 121.94(17) . . ?
N1 C3 C4 107.49(15) . . ?
C5 C4 N2 133.45(15) . . ?
C5 C4 C3 120.51(17) . . ?
N2 C4 C3 106.03(15) . . ?
C4 C5 C6 118.05(16) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 120.39(19) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 N1 127.25(16) . . ?
O1 C7 N2 127.09(16) . . ?
N1 C7 N2 105.65(16) . . ?
N2 C8 C9 111.66(15) . . ?
N2 C8 C12 113.97(16) . . ?
C9 C8 C12 109.44(15) . . ?
N2 C8 H8 107.1 . . ?
C9 C8 H8 107.1 . . ?
C12 C8 H8 107.1 . . ?
C10 C9 C8 110.61(17) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N3 C10 C9 111.89(17) . . ?
N3 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N3 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N3 C11 C12 111.79(16) . . ?
N3 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C8 109.87(17) . . ?
C11 C12 H12A 109.7 . . ?
C8 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C8 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N3 C13 C14 112.63(17) . . ?
N3 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N3 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 109.47(18) . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
N4 C15 C14 111.86(19) . . ?
N4 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
N4 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
O2 C16 N4 126.3(2) . . ?
O2 C16 N5 127.1(2) . . ?
N4 C16 N5 106.62(19) . . ?
C18 C17 N5 132.3(2) . . ?
C18 C17 C22 121.1(2) . . ?
N5 C17 C22 106.59(19) . . ?
C19 C18 C17 117.3(2) . . ?
C19 C18 H18 121.3 . . ?
C17 C18 H18 121.3 . . ?
C18 C19 C20 121.5(3) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C22 C21 C20 117.2(2) . . ?
C22 C21 H21 121.4 . . ?
C20 C21 H21 121.4 . . ?
C21 C22 N4 131.7(2) . . ?
C21 C22 C17 121.5(2) . . ?
N4 C22 C17 106.85(18) . . ?
C3 N1 C7 110.67(14) . . ?
C3 N1 H1N 124.9(16) . . ?
C7 N1 H1N 124.4(16) . . ?
C7 N2 C4 110.15(13) . . ?
C7 N2 C8 120.37(15) . . ?
C4 N2 C8 129.40(14) . . ?
C10 N3 C11 111.22(14) . . ?
C10 N3 C13 110.10(15) . . ?
C11 N3 C13 111.44(15) . . ?
C10 N3 H3N 108.4(11) . . ?
C11 N3 H3N 109.9(13) . . ?
C13 N3 H3N 105.6(10) . . ?
C16 N4 C22 109.71(17) . . ?
C16 N4 C15 124.30(19) . . ?
C22 N4 C15 125.98(18) . . ?
C16 N5 C17 110.22(18) . . ?
C16 N5 H5N 124.5(19) . . ?
C17 N5 H5N 124.1(19) . . ?
O3 C23 O4 124.9(3) . . ?
O3 C23 C24 118.1(2) . . ?
O4 C23 C24 117.0(2) . . ?
C25 C24 C29 120.0 . . ?
C25 C24 C23 120.27(14) . . ?
C29 C24 C23 119.68(14) . . ?
O5 C25 C26 118.65(18) . . ?
O5 C25 C24 121.34(18) . . ?
C26 C25 C24 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C24 120.0 . . ?
C28 C29 H29 120.0 . . ?
C24 C29 H29 120.0 . . ?
C25 O5 H5O 90(3) . . ?
H1W O1W H2W 119(4) . . ?
H3W O2W H4W 116(4) . . ?
H5W O3W H6W 107(3) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.8(3) . . . . ?
Cl1 C1 C2 C3 179.13(16) . . . . ?
C1 C2 C3 N1 179.3(2) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 1.8(3) . . . . ?
N1 C3 C4 C5 -177.80(19) . . . . ?
C2 C3 C4 N2 -179.49(19) . . . . ?
N1 C3 C4 N2 0.9(2) . . . . ?
N2 C4 C5 C6 179.4(2) . . . . ?
C3 C4 C5 C6 -2.3(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
Cl1 C1 C6 C5 -179.64(18) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
N2 C8 C9 C10 175.07(16) . . . . ?
C12 C8 C9 C10 -57.8(2) . . . . ?
C8 C9 C10 N3 56.2(2) . . . . ?
N3 C11 C12 C8 -57.4(2) . . . . ?
N2 C8 C12 C11 -175.91(17) . . . . ?
C9 C8 C12 C11 58.3(2) . . . . ?
N3 C13 C14 C15 162.73(18) . . . . ?
C13 C14 C15 N4 -174.68(18) . . . . ?
N5 C17 C18 C19 178.4(3) . . . . ?
C22 C17 C18 C19 0.3(4) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C21 -1.1(6) . . . . ?
C19 C20 C21 C22 1.1(5) . . . . ?
C20 C21 C22 N4 180.0(3) . . . . ?
C20 C21 C22 C17 -0.5(4) . . . . ?
C18 C17 C22 C21 -0.2(4) . . . . ?
N5 C17 C22 C21 -178.7(2) . . . . ?
C18 C17 C22 N4 179.4(2) . . . . ?
N5 C17 C22 N4 0.9(2) . . . . ?
C2 C3 N1 C7 179.6(2) . . . . ?
C4 C3 N1 C7 -0.9(2) . . . . ?
O1 C7 N1 C3 179.3(2) . . . . ?
N2 C7 N1 C3 0.4(2) . . . . ?
O1 C7 N2 C4 -178.7(2) . . . . ?
N1 C7 N2 C4 0.2(2) . . . . ?
O1 C7 N2 C8 -1.6(3) . . . . ?
N1 C7 N2 C8 177.28(17) . . . . ?
C5 C4 N2 C7 177.8(2) . . . . ?
C3 C4 N2 C7 -0.7(2) . . . . ?
C5 C4 N2 C8 1.0(4) . . . . ?
C3 C4 N2 C8 -177.44(19) . . . . ?
C9 C8 N2 C7 -102.7(2) . . . . ?
C12 C8 N2 C7 132.6(2) . . . . ?
C9 C8 N2 C4 73.7(3) . . . . ?
C12 C8 N2 C4 -50.9(3) . . . . ?
C9 C10 N3 C11 -54.3(2) . . . . ?
C9 C10 N3 C13 -178.36(18) . . . . ?
C12 C11 N3 C10 55.2(2) . . . . ?
C12 C11 N3 C13 178.45(16) . . . . ?
C14 C13 N3 C10 -168.49(19) . . . . ?
C14 C13 N3 C11 67.6(2) . . . . ?
O2 C16 N4 C22 -179.2(2) . . . . ?
N5 C16 N4 C22 0.5(3) . . . . ?
O2 C16 N4 C15 0.1(4) . . . . ?
N5 C16 N4 C15 179.73(19) . . . . ?
C21 C22 N4 C16 178.7(3) . . . . ?
C17 C22 N4 C16 -0.9(2) . . . . ?
C21 C22 N4 C15 -0.5(4) . . . . ?
C17 C22 N4 C15 179.9(2) . . . . ?
C14 C15 N4 C16 -101.2(2) . . . . ?
C14 C15 N4 C22 77.9(3) . . . . ?
O2 C16 N5 C17 179.8(2) . . . . ?
N4 C16 N5 C17 0.1(3) . . . . ?
C18 C17 N5 C16 -178.9(2) . . . . ?
C22 C17 N5 C16 -0.6(3) . . . . ?
O3 C23 C24 C25 -163.9(2) . . . . ?
O4 C23 C24 C25 14.7(3) . . . . ?
O3 C23 C24 C29 13.7(3) . . . . ?
O4 C23 C24 C29 -167.7(2) . . . . ?
C29 C24 C25 O5 178.9(3) . . . . ?
C23 C24 C25 O5 -3.5(3) . . . . ?
C29 C24 C25 C26 0.0 . . . . ?
C23 C24 C25 C26 177.6(2) . . . . ?
O5 C25 C26 C27 -178.9(2) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C24 0.0 . . . . ?
C25 C24 C29 C28 0.0 . . . . ?
C23 C24 C29 C28 -177.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O2W 0.87(2) 1.97(2) 2.828(2) 168(2) 2_566 yes
N5 H5N O2 0.82(2) 1.99(3) 2.794(2) 165(3) 2_577 yes
O1W H2W O3 0.884(19) 1.99(2) 2.826(3) 158(4) 1_455 yes
O2W H4W O5 0.871(19) 2.10(3) 2.925(4) 157(5) 1_465 yes
O5 H5O O4 0.902(19) 1.95(5) 2.511(4) 118(4) . yes
N3 H3N O3 0.95(2) 1.83(2) 2.719(2) 155.7(18) . yes
O1W H1W O2 0.864(19) 1.94(2) 2.791(3) 166(4) . yes
O2W H3W O1W 0.891(19) 1.86(2) 2.734(3) 167(5) . yes
O3W H6W O4 0.87(2) 2.16(3) 3.004(6) 163(7) . yes

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB560_0m
_database_code_depnum_ccdc_archive 'CCDC 2240371'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-09-26 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Domperidone mandelate hydrate'
_chemical_name_common            'Domperidone mandelate hydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 Cl N5 O2, C8 H7 O3, 2(H2 O), 0.268(O)'
_chemical_formula_sum            'C30 H36 Cl N5 O7.27'
_chemical_formula_weight         618.38

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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3045(2)
_cell_length_b                   10.2362(2)
_cell_length_c                   21.8241(5)
_cell_angle_alpha                80.9935(7)
_cell_angle_beta                 82.5939(7)
_cell_angle_gamma                79.5884(7)
_cell_volume                     1576.61(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      29.3

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             652.3
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6811
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            47636
_diffrn_reflns_av_unetI/netI     0.1272
_diffrn_reflns_av_R_equivalents  0.1514
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.131
_diffrn_reflns_theta_max         30.754
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9773
_reflns_number_gt                5171
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0913P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9773
_refine_ls_number_parameters     414
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1624
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1887
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2780(2) 1.10553(19) 0.48814(10) 0.0384(4) Uani 1 1 d . . . . .
C2 C 0.2347(2) 1.0185(2) 0.54090(9) 0.0372(4) Uani 1 1 d . . . . .
H2 H 0.220853 1.043930 0.580547 0.045 Uiso 1 1 calc R U . . .
C3 C 0.2128(2) 0.89128(18) 0.53184(9) 0.0330(3) Uani 1 1 d . . . . .
C4 C 0.2329(2) 0.85286(18) 0.47200(9) 0.0331(3) Uani 1 1 d . . . . .
C5 C 0.2799(3) 0.9412(2) 0.42018(9) 0.0398(4) Uani 1 1 d . . . . .
H5 H 0.296642 0.915737 0.380495 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3018(3) 1.0695(2) 0.42872(11) 0.0427(4) Uani 1 1 d . . . . .
H6 H 0.332488 1.130932 0.394459 0.051 Uiso 1 1 calc R U . . .
C7 C 0.1664(2) 0.67614(19) 0.54359(8) 0.0340(3) Uani 1 1 d . . . . .
C8 C 0.2185(3) 0.62947(19) 0.43386(8) 0.0343(3) Uani 1 1 d . . . . .
H8 H 0.172995 0.547629 0.454614 0.041 Uiso 1 1 calc R U . . .
C9 C 0.4242(3) 0.5903(2) 0.41063(9) 0.0377(4) Uani 1 1 d . . . . .
H9A H 0.476647 0.670838 0.394152 0.045 Uiso 1 1 calc R U . . .
H9B H 0.491833 0.544644 0.445411 0.045 Uiso 1 1 calc R U . . .
C10 C 0.4506(3) 0.4998(2) 0.36041(9) 0.0414(4) Uani 1 1 d . . . . .
H10A H 0.581922 0.482191 0.344873 0.050 Uiso 1 1 calc R U . . .
H10B H 0.411540 0.414871 0.377927 0.050 Uiso 1 1 calc R U . . .
C11 C 0.1344(3) 0.5923(2) 0.33126(9) 0.0404(4) Uani 1 1 d . . . . .
H11A H 0.091745 0.508818 0.349222 0.048 Uiso 1 1 calc R U . . .
H11B H 0.062708 0.631921 0.296595 0.048 Uiso 1 1 calc R U . . .
C12 C 0.1015(3) 0.6867(2) 0.37989(9) 0.0390(4) Uani 1 1 d . . . . .
H12A H -0.030066 0.700669 0.395486 0.047 Uiso 1 1 calc R U . . .
H12B H 0.134328 0.772766 0.361034 0.047 Uiso 1 1 calc R U . . .
C13 C 0.3733(3) 0.4804(2) 0.25630(10) 0.0447(4) Uani 1 1 d . . . . .
H13A H 0.305189 0.405662 0.267589 0.054 Uiso 1 1 calc R U . . .
H13B H 0.505655 0.444176 0.250633 0.054 Uiso 1 1 calc R U . . .
C14 C 0.3138(3) 0.5597(3) 0.19537(10) 0.0510(5) Uani 1 1 d . . . . .
H14A H 0.369992 0.640467 0.186143 0.061 Uiso 1 1 calc R U . . .
H14B H 0.178851 0.585908 0.198817 0.061 Uiso 1 1 calc R U . . .
C15 C 0.3761(4) 0.4738(3) 0.14334(11) 0.0551(6) Uani 1 1 d . . . . .
H15A H 0.511146 0.448665 0.140051 0.066 Uiso 1 1 calc R U . . .
H15B H 0.321860 0.392316 0.153475 0.066 Uiso 1 1 calc R U . . .
C16 C 0.1634(4) 0.5277(3) 0.05950(11) 0.0564(6) Uani 1 1 d . . . . .
C17 C 0.4134(3) 0.6336(3) 0.04317(11) 0.0537(6) Uani 1 1 d . . . . .
C18 C 0.5764(4) 0.6823(4) 0.04600(16) 0.0702(8) Uani 1 1 d . . . . .
H18 H 0.645679 0.655546 0.080000 0.084 Uiso 1 1 calc R U . . .
C19 C 0.6316(5) 0.7724(4) -0.00378(19) 0.0870(11) Uani 1 1 d . . . . .
H19 H 0.740621 0.806980 -0.003368 0.104 Uiso 1 1 calc R U . . .
C20 C 0.5286(6) 0.8124(4) -0.05428(19) 0.0907(11) Uani 1 1 d . . . . .
H20 H 0.570675 0.873057 -0.087066 0.109 Uiso 1 1 calc R U . . .
C21 C 0.3644(5) 0.7649(3) -0.05755(14) 0.0703(8) Uani 1 1 d . . . . .
H21 H 0.294457 0.792837 -0.091342 0.084 Uiso 1 1 calc R U . . .
C22 C 0.3108(4) 0.6742(3) -0.00801(12) 0.0552(6) Uani 1 1 d . . . . .
Cl1 Cl 0.30450(8) 1.26639(5) 0.49761(3) 0.05169(15) Uani 1 1 d . . . . .
O1 O 0.1394(2) 0.56383(15) 0.56682(7) 0.0443(3) Uani 1 1 d . . . . .
O2 O 0.0515(3) 0.4523(3) 0.08379(8) 0.0702(6) Uani 1 1 d . . . . .
N1 N 0.1733(2) 0.78267(17) 0.57397(8) 0.0375(3) Uani 1 1 d D . . . .
H1N H 0.159(4) 0.778(3) 0.6138(8) 0.067(9) Uiso 1 1 d D . . . .
N2 N 0.1995(2) 0.72091(16) 0.48042(7) 0.0341(3) Uani 1 1 d . . . . .
N3 N 0.3383(2) 0.56418(18) 0.30799(7) 0.0350(3) Uani 1 1 d . . . . .
H3N H 0.380(3) 0.638(3) 0.2940(12) 0.042(6) Uiso 1 1 d . . . . .
N4 N 0.3203(3) 0.5437(2) 0.08387(9) 0.0537(5) Uani 1 1 d . . . . .
N5 N 0.1578(3) 0.6084(3) 0.00369(10) 0.0591(6) Uani 1 1 d D . . . .
H5N H 0.084(4) 0.598(4) -0.0257(13) 0.085(10) Uiso 1 1 d D . . . .
C23 C 0.6385(3) 0.7777(3) 0.26136(12) 0.0525(5) Uani 1 1 d . . . . .
C24 C 0.7480(4) 0.8948(3) 0.25747(14) 0.0596(6) Uani 1 1 d . . . . .
H24 H 0.819224 0.878615 0.293802 0.072 Uiso 1 1 calc R U . . .
C25 C 0.8853(2) 0.9050(2) 0.19941(8) 0.0522(5) Uani 1 1 d G . . . .
C26 C 1.0667(2) 0.9197(2) 0.20632(8) 0.0758(10) Uani 1 1 d G . . . .
H26 H 1.100077 0.923391 0.245650 0.091 Uiso 1 1 calc R U . . .
C27 C 1.1982(2) 0.9290(3) 0.15445(10) 0.0877(12) Uani 1 1 d G . . . .
H27 H 1.319564 0.938879 0.159078 0.105 Uiso 1 1 calc R U . . .
C28 C 1.1483(3) 0.9235(3) 0.09567(9) 0.0812(9) Uani 1 1 d G . . . .
H28 H 1.236305 0.929734 0.060967 0.097 Uiso 1 1 calc R U . . .
C29 C 0.9669(3) 0.9088(3) 0.08876(7) 0.0930(12) Uani 1 1 d G . . . .
H29 H 0.933558 0.905100 0.049427 0.112 Uiso 1 1 calc R U . . .
C30 C 0.8354(2) 0.8995(3) 0.14062(9) 0.0834(11) Uani 1 1 d G . . . .
H30 H 0.714068 0.889612 0.135999 0.100 Uiso 1 1 calc R U . . .
O3 O 0.7306(3) 0.6654(2) 0.25721(13) 0.0832(7) Uani 1 1 d . . . . .
O4 O 0.4659(2) 0.8051(2) 0.27332(9) 0.0599(5) Uani 1 1 d . . . . .
O5 O 0.6232(4) 1.0165(3) 0.26012(16) 0.0976(9) Uani 1 1 d D . . . .
H5O H 0.521(8) 0.990(11) 0.254(4) 0.31(5) Uiso 1 1 d D . . . .
O1W O 0.8633(6) 0.4324(3) 0.20666(15) 0.1127(10) Uani 1 1 d D . . . .
H1W H 0.840(8) 0.510(3) 0.218(3) 0.169 Uiso 1 1 d D U . . .
H2W H 0.903(8) 0.441(7) 0.1681(8) 0.169 Uiso 1 1 d D U . . .
O2W O 0.8101(5) 0.2158(3) 0.29605(11) 0.1033(10) Uani 1 1 d D . . . .
H3W H 0.842(7) 0.271(5) 0.2645(17) 0.155 Uiso 1 1 d D U . . .
H4W H 0.745(7) 0.156(4) 0.292(3) 0.155 Uiso 1 1 d D U . . .
O3W O 0.235(2) 1.154(2) 0.2653(10) 0.188(12) Uani 0.268(13) 1 d . . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.381(3) . ?
C1 C6 1.384(3) . ?
C1 Cl1 1.7389(19) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9300 . ?
C3 N1 1.376(2) . ?
C3 C4 1.404(2) . ?
C4 C5 1.381(3) . ?
C4 N2 1.395(2) . ?
C5 C6 1.395(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.221(2) . ?
C7 N1 1.373(2) . ?
C7 N2 1.388(2) . ?
C8 N2 1.464(2) . ?
C8 C12 1.524(3) . ?
C8 C9 1.525(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.515(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N3 1.492(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.502(3) . ?
C11 C12 1.513(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.491(2) . ?
C13 C14 1.517(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.518(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N4 1.450(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.239(3) . ?
C16 N5 1.361(3) . ?
C16 N4 1.369(3) . ?
C17 N4 1.383(3) . ?
C17 C18 1.383(3) . ?
C17 C22 1.393(3) . ?
C18 C19 1.378(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(4) . ?
C21 H21 0.9300 . ?
C22 N5 1.383(3) . ?
N1 H1N 0.856(17) . ?
N3 H3N 0.86(3) . ?
N5 H5N 0.922(17) . ?
C23 O3 1.232(4) . ?
C23 O4 1.244(3) . ?
C23 C24 1.543(3) . ?
C24 O5 1.409(4) . ?
C24 C25 1.514(3) . ?
C24 H24 0.9800 . ?
C25 C26 1.3900 . ?
C25 C30 1.3900 . ?
C26 C27 1.3900 . ?
C26 H26 0.9300 . ?
C27 C28 1.3900 . ?
C27 H27 0.9300 . ?
C28 C29 1.3900 . ?
C28 H28 0.9300 . ?
C29 C30 1.3900 . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
O5 H5O 0.867(10) . ?
O1W H1W 0.855(10) . ?
O1W H2W 0.850(10) . ?
O2W H3W 0.858(10) . ?
O2W H4W 0.859(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.75(18) . . ?
C2 C1 Cl1 117.99(16) . . ?
C6 C1 Cl1 119.25(16) . . ?
C1 C2 C3 116.68(18) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
N1 C3 C2 130.82(17) . . ?
N1 C3 C4 107.42(16) . . ?
C2 C3 C4 121.76(17) . . ?
C5 C4 N2 133.56(17) . . ?
C5 C4 C3 120.24(17) . . ?
N2 C4 C3 106.19(16) . . ?
C4 C5 C6 118.48(18) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 120.06(19) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 N1 127.60(18) . . ?
O1 C7 N2 126.36(18) . . ?
N1 C7 N2 106.04(16) . . ?
N2 C8 C12 112.66(16) . . ?
N2 C8 C9 110.09(14) . . ?
C12 C8 C9 111.34(15) . . ?
N2 C8 H8 107.5 . . ?
C12 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C10 C9 C8 112.06(15) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 C9 110.35(16) . . ?
N3 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N3 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N3 C11 C12 110.84(13) . . ?
N3 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C8 110.68(17) . . ?
C11 C12 H12A 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N3 C13 C14 112.13(18) . . ?
N3 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 109.2(2) . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
N4 C15 C14 111.8(2) . . ?
N4 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
N4 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
O2 C16 N5 127.4(2) . . ?
O2 C16 N4 125.9(2) . . ?
N5 C16 N4 106.7(2) . . ?
N4 C17 C18 132.1(3) . . ?
N4 C17 C22 106.90(19) . . ?
C18 C17 C22 121.0(3) . . ?
C19 C18 C17 117.1(3) . . ?
C19 C18 H18 121.5 . . ?
C17 C18 H18 121.5 . . ?
C18 C19 C20 121.5(3) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C21 122.0(3) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C22 C21 C20 116.3(3) . . ?
C22 C21 H21 121.9 . . ?
C20 C21 H21 121.9 . . ?
C21 C22 N5 131.3(2) . . ?
C21 C22 C17 122.1(2) . . ?
N5 C22 C17 106.6(2) . . ?
C7 N1 C3 110.49(16) . . ?
C7 N1 H1N 123(2) . . ?
C3 N1 H1N 126(2) . . ?
C7 N2 C4 109.82(15) . . ?
C7 N2 C8 121.09(15) . . ?
C4 N2 C8 128.60(16) . . ?
C13 N3 C10 110.87(16) . . ?
C13 N3 C11 112.10(14) . . ?
C10 N3 C11 110.28(15) . . ?
C13 N3 H3N 107.3(18) . . ?
C10 N3 H3N 105.5(15) . . ?
C11 N3 H3N 110.6(16) . . ?
C16 N4 C17 109.7(2) . . ?
C16 N4 C15 123.5(2) . . ?
C17 N4 C15 126.78(18) . . ?
C16 N5 C22 110.1(2) . . ?
C16 N5 H5N 122(2) . . ?
C22 N5 H5N 126(2) . . ?
O3 C23 O4 126.5(2) . . ?
O3 C23 C24 117.2(2) . . ?
O4 C23 C24 116.0(2) . . ?
O5 C24 C25 110.3(2) . . ?
O5 C24 C23 110.2(2) . . ?
C25 C24 C23 112.3(2) . . ?
O5 C24 H24 108.0 . . ?
C25 C24 H24 108.0 . . ?
C23 C24 H24 108.0 . . ?
C26 C25 C30 120.0 . . ?
C26 C25 C24 117.79(14) . . ?
C30 C25 C24 122.21(14) . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C29 120.0 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C25 120.0 . . ?
C29 C30 H30 120.0 . . ?
C25 C30 H30 120.0 . . ?
C24 O5 H5O 99(7) . . ?
H1W O1W H2W 108(6) . . ?
H3W O2W H4W 121(5) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.9(3) . . . . ?
Cl1 C1 C2 C3 179.47(13) . . . . ?
C1 C2 C3 N1 178.82(18) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
N1 C3 C4 C5 -177.69(16) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
N1 C3 C4 N2 1.43(19) . . . . ?
C2 C3 C4 N2 -179.29(15) . . . . ?
N2 C4 C5 C6 179.49(18) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
Cl1 C1 C6 C5 -179.59(14) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
N2 C8 C9 C10 -177.78(16) . . . . ?
C12 C8 C9 C10 -52.1(2) . . . . ?
C8 C9 C10 N3 55.4(2) . . . . ?
N3 C11 C12 C8 -56.9(2) . . . . ?
N2 C8 C12 C11 176.69(15) . . . . ?
C9 C8 C12 C11 52.4(2) . . . . ?
N3 C13 C14 C15 172.75(18) . . . . ?
C13 C14 C15 N4 179.07(18) . . . . ?
N4 C17 C18 C19 179.7(3) . . . . ?
C22 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 C20 0.1(6) . . . . ?
C18 C19 C20 C21 0.3(7) . . . . ?
C19 C20 C21 C22 -0.8(6) . . . . ?
C20 C21 C22 N5 179.9(3) . . . . ?
C20 C21 C22 C17 1.0(5) . . . . ?
N4 C17 C22 C21 179.6(3) . . . . ?
C18 C17 C22 C21 -0.7(4) . . . . ?
N4 C17 C22 N5 0.5(3) . . . . ?
C18 C17 C22 N5 -179.8(3) . . . . ?
O1 C7 N1 C3 178.05(18) . . . . ?
N2 C7 N1 C3 -1.1(2) . . . . ?
C2 C3 N1 C7 -179.42(17) . . . . ?
C4 C3 N1 C7 -0.2(2) . . . . ?
O1 C7 N2 C4 -177.14(18) . . . . ?
N1 C7 N2 C4 2.00(19) . . . . ?
O1 C7 N2 C8 -4.5(3) . . . . ?
N1 C7 N2 C8 174.65(15) . . . . ?
C5 C4 N2 C7 176.8(2) . . . . ?
C3 C4 N2 C7 -2.14(19) . . . . ?
C5 C4 N2 C8 4.9(3) . . . . ?
C3 C4 N2 C8 -174.09(16) . . . . ?
C12 C8 N2 C7 132.26(18) . . . . ?
C9 C8 N2 C7 -102.80(19) . . . . ?
C12 C8 N2 C4 -56.6(2) . . . . ?
C9 C8 N2 C4 68.3(2) . . . . ?
C14 C13 N3 C10 -161.69(18) . . . . ?
C14 C13 N3 C11 74.6(2) . . . . ?
C9 C10 N3 C13 176.06(17) . . . . ?
C9 C10 N3 C11 -59.2(2) . . . . ?
C12 C11 N3 C13 -175.33(17) . . . . ?
C12 C11 N3 C10 60.6(2) . . . . ?
O2 C16 N4 C17 178.6(3) . . . . ?
N5 C16 N4 C17 -0.4(3) . . . . ?
O2 C16 N4 C15 -0.8(5) . . . . ?
N5 C16 N4 C15 -179.8(2) . . . . ?
C18 C17 N4 C16 -179.7(3) . . . . ?
C22 C17 N4 C16 -0.1(3) . . . . ?
C18 C17 N4 C15 -0.3(5) . . . . ?
C22 C17 N4 C15 179.3(2) . . . . ?
C14 C15 N4 C16 -97.4(3) . . . . ?
C14 C15 N4 C17 83.3(3) . . . . ?
O2 C16 N5 C22 -178.2(3) . . . . ?
N4 C16 N5 C22 0.7(3) . . . . ?
C21 C22 N5 C16 -179.8(3) . . . . ?
C17 C22 N5 C16 -0.8(3) . . . . ?
O3 C23 C24 O5 177.3(3) . . . . ?
O4 C23 C24 O5 -8.1(4) . . . . ?
O3 C23 C24 C25 54.0(3) . . . . ?
O4 C23 C24 C25 -131.5(2) . . . . ?
O5 C24 C25 C26 104.2(2) . . . . ?
C23 C24 C25 C26 -132.5(2) . . . . ?
O5 C24 C25 C30 -76.1(2) . . . . ?
C23 C24 C25 C30 47.3(3) . . . . ?
C30 C25 C26 C27 0.0 . . . . ?
C24 C25 C26 C27 179.7(2) . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
C28 C29 C30 C25 0.0 . . . . ?
C26 C25 C30 C29 0.0 . . . . ?
C24 C25 C30 C29 -179.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2W H4W O5 0.859(10) 2.063(18) 2.902(4) 166(5) 1_545 yes
N1 H1N O2W 0.856(17) 2.021(18) 2.857(3) 165(3) 2_666 yes
N3 H3N O3 0.86(3) 2.63(2) 3.226(3) 127(2) . yes
N3 H3N O4 0.86(3) 1.90(3) 2.754(2) 173(3) . yes
N5 H5N O2 0.922(17) 1.884(19) 2.799(2) 171(4) 2_565 yes
O5 H5O O4 0.867(10) 1.98(9) 2.589(3) 127(9) . yes
O5 H5O O3W 0.867(10) 2.45(10) 2.928(17) 116(8) . yes
O1W H1W O3 0.855(10) 1.92(2) 2.749(4) 164(6) . yes
O1W H2W O2 0.850(10) 2.011(17) 2.846(3) 167(6) 1_655 yes
O2W H3W O1W 0.858(10) 1.93(2) 2.763(4) 163(6) . yes

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.078


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB706_0m
_database_code_depnum_ccdc_archive 'CCDC 2240370'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-09-26 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Domperidone nicotinate hydrate'
_chemical_name_common            'Domperidone nicotinate hydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C22 H25 Cl N5 O2), 2(C6 H4 N O2), 4(H2 O), O'
_chemical_formula_sum            'C56 H66 Cl2 N12 O13'
_chemical_formula_weight         1186.10

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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.471(5)
_cell_length_b                   17.466(6)
_cell_length_c                   11.749(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.939(6)
_cell_angle_gamma                90
_cell_volume                     2965.8(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9861
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.11

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.182
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5321
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            58401
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_av_R_equivalents  0.0800
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.332
_diffrn_reflns_theta_max         30.526
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             8997
_reflns_number_gt                4514
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1267P)²+0.3833P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8997
_refine_ls_number_parameters     460
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.1473
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2394
_refine_ls_wR_factor_gt          0.1861
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.60061(15) 0.43505(14) 0.8964(2) 0.0505(5) Uani 1 1 d . . . . .
C2 C 0.61190(14) 0.50878(14) 0.93920(19) 0.0495(5) Uani 1 1 d . . . . .
H2 H 0.651169 0.519161 1.002457 0.059 Uiso 1 1 calc R U . . .
C3 C 0.56207(14) 0.56555(13) 0.88330(18) 0.0447(5) Uani 1 1 d . . . . .
C4 C 0.50350(14) 0.55067(13) 0.78692(17) 0.0432(5) Uani 1 1 d . . . . .
C5 C 0.49389(16) 0.47708(13) 0.7452(2) 0.0515(5) Uani 1 1 d . . . . .
H5 H 0.455645 0.466630 0.681013 0.062 Uiso 1 1 calc R U . . .
C6 C 0.54372(16) 0.41843(14) 0.8026(2) 0.0530(6) Uani 1 1 d . . . . .
H6 H 0.538103 0.368177 0.777021 0.064 Uiso 1 1 calc R U . . .
C7 C 0.49475(15) 0.67747(14) 0.82966(19) 0.0477(5) Uani 1 1 d . . . . .
C8 C 0.39115(15) 0.63729(13) 0.66667(18) 0.0473(5) Uani 1 1 d . . . . .
H8 H 0.378842 0.692406 0.669791 0.057 Uiso 1 1 calc R U . . .
C9 C 0.30118(15) 0.59670(16) 0.69092(19) 0.0546(6) Uani 1 1 d . . . . .
H9A H 0.309902 0.541723 0.686972 0.066 Uiso 1 1 calc R U . . .
H9B H 0.283280 0.609422 0.767081 0.066 Uiso 1 1 calc R U . . .
C10 C 0.22559(16) 0.62114(17) 0.60421(19) 0.0594(6) Uani 1 1 d . . . . .
H10A H 0.168837 0.594221 0.619088 0.071 Uiso 1 1 calc R U . . .
H10B H 0.214231 0.675563 0.612202 0.071 Uiso 1 1 calc R U . . .
C11 C 0.34094(16) 0.64253(15) 0.46044(19) 0.0550(6) Uani 1 1 d . . . . .
H11A H 0.333128 0.697659 0.462733 0.066 Uiso 1 1 calc R U . . .
H11B H 0.358023 0.628698 0.384375 0.066 Uiso 1 1 calc R U . . .
C12 C 0.41746(16) 0.61934(17) 0.54556(19) 0.0572(6) Uani 1 1 d . . . . .
H12A H 0.473733 0.646558 0.529438 0.069 Uiso 1 1 calc R U . . .
H12B H 0.429289 0.564918 0.538604 0.069 Uiso 1 1 calc R U . . .
C13 C 0.17406(17) 0.62785(16) 0.4036(2) 0.0597(6) Uani 1 1 d . . . . .
H13A H 0.162774 0.682193 0.412780 0.072 Uiso 1 1 calc R U . . .
H13B H 0.118519 0.600882 0.423358 0.072 Uiso 1 1 calc R U . . .
C14 C 0.19109(16) 0.61217(16) 0.27928(19) 0.0563(6) Uani 1 1 d . . . . .
H14A H 0.227971 0.652954 0.248704 0.068 Uiso 1 1 calc R U . . .
H14B H 0.224357 0.564337 0.272220 0.068 Uiso 1 1 calc R U . . .
C15 C 0.09805(17) 0.60759(17) 0.21419(19) 0.0614(7) Uani 1 1 d . . . . .
H15A H 0.063625 0.564810 0.243284 0.074 Uiso 1 1 calc R U . . .
H15B H 0.063487 0.653910 0.228370 0.074 Uiso 1 1 calc R U . . .
C16 C 0.08729(16) 0.65553(16) 0.01395(19) 0.0541(6) Uani 1 1 d . . . . .
C17 C 0.11177(15) 0.54579(15) -0.0814(2) 0.0516(6) Uani 1 1 d . . . . .
C18 C 0.12082(17) 0.48904(16) -0.1613(2) 0.0636(7) Uani 1 1 d . . . . .
H18 H 0.116181 0.499791 -0.238887 0.076 Uiso 1 1 calc R U . . .
C19 C 0.1370(2) 0.41570(19) -0.1220(3) 0.0786(9) Uani 1 1 d . . . . .
H19 H 0.143917 0.376418 -0.174306 0.094 Uiso 1 1 calc R U . . .
C20 C 0.1432(2) 0.39894(19) -0.0066(3) 0.0827(9) Uani 1 1 d . . . . .
H20 H 0.153426 0.348683 0.016925 0.099 Uiso 1 1 calc R U . . .
C21 C 0.13447(19) 0.45613(18) 0.0745(3) 0.0708(8) Uani 1 1 d . . . . .
H21 H 0.139099 0.445216 0.152064 0.085 Uiso 1 1 calc R U . . .
C22 C 0.11867(15) 0.52954(15) 0.0354(2) 0.0532(6) Uani 1 1 d . . . . .
Cl1 Cl 0.66072(5) 0.36055(4) 0.96679(6) 0.0692(2) Uani 1 1 d . . . . .
N1 N 0.55589(13) 0.64301(11) 0.90602(17) 0.0519(5) Uani 1 1 d . . . . .
H1N H 0.586267 0.666251 0.960558 0.062 Uiso 1 1 calc R U . . .
N2 N 0.46426(12) 0.62104(10) 0.75344(15) 0.0465(4) Uani 1 1 d . . . . .
N3 N 0.25152(12) 0.60467(12) 0.48485(15) 0.0455(4) Uani 1 1 d . . . . .
H3N H 0.2563(17) 0.5491(17) 0.478(2) 0.059(7) Uiso 1 1 d . . . . .
N4 N 0.10431(13) 0.59833(12) 0.09205(15) 0.0536(5) Uani 1 1 d . . . . .
N5 N 0.09407(14) 0.62360(12) -0.09123(16) 0.0548(5) Uani 1 1 d . . . . .
H5N H 0.088204 0.648197 -0.154596 0.066 Uiso 1 1 calc R U . . .
O1 O 0.47076(13) 0.74457(10) 0.82845(15) 0.0620(5) Uani 1 1 d . . . . .
O2 O 0.06991(15) 0.72293(11) 0.03505(15) 0.0718(5) Uani 1 1 d . . . . .
C23 C 0.3313(2) 0.20082(17) 0.3033(3) 0.0701(7) Uani 1 1 d . . . . .
H23 H 0.356465 0.155518 0.277096 0.084 Uiso 1 1 calc R U . A 1
C28 C 0.3420(2) 0.29258(19) 0.4379(3) 0.0759(8) Uani 1 1 d D . . . .
H28 H 0.368909 0.314151 0.503969 0.091 Uiso 1 1 calc R U . B 1
C24 C 0.2694(5) 0.2298(4) 0.2368(6) 0.0699(15) Uani 0.619(4) 1 d D U P C 1
H24 H 0.249007 0.205140 0.170013 0.084 Uiso 0.619(4) 1 calc R U P C 1
C25 C 0.2334(4) 0.2994(4) 0.2674(5) 0.0674(12) Uani 0.619(4) 1 d D U P C 1
H25 H 0.186203 0.322237 0.222749 0.081 Uiso 0.619(4) 1 calc R U P C 1
C26 C 0.2688(4) 0.3350(3) 0.3660(5) 0.0582(11) Uani 0.619(4) 1 d D U P C 1
C27 C 0.2311(3) 0.4102(3) 0.4012(4) 0.0663(11) Uani 0.619(4) 1 d D U P C 1
O3 O 0.2824(5) 0.4507(3) 0.4676(6) 0.0903(15) Uani 0.619(4) 1 d . U P C 1
O4 O 0.1516(2) 0.42959(18) 0.3670(3) 0.0771(11) Uani 0.619(4) 1 d . U P C 1
C24D C 0.2747(10) 0.2640(6) 0.2421(10) 0.067(2) Uani 0.381(4) 1 d D U P C 2
H24D H 0.247739 0.256358 0.169447 0.081 Uiso 0.381(4) 1 calc R U P C 2
C25D C 0.2651(6) 0.3323(5) 0.2983(9) 0.0653(16) Uani 0.381(4) 1 d D U P C 2
H25D H 0.230374 0.370595 0.261377 0.078 Uiso 0.381(4) 1 calc R U P C 2
C26D C 0.3029(6) 0.3477(4) 0.4039(7) 0.0568(16) Uani 0.381(4) 1 d D U P C 2
C27D C 0.2960(9) 0.4206(5) 0.4655(11) 0.066(2) Uani 0.381(4) 1 d D U P C 2
O3D O 0.3450(5) 0.4299(4) 0.5517(7) 0.118(3) Uani 0.381(4) 1 d . U P C 2
O4D O 0.2377(5) 0.4685(4) 0.4213(6) 0.0817(18) Uani 0.381(4) 1 d . U P C 2
N6 N 0.36645(16) 0.22353(14) 0.4032(2) 0.0687(6) Uani 1 1 d . . . . .
O1W O 0.0074(2) 0.8195(2) 0.2055(2) 0.1169(9) Uani 1 1 d D . . . .
H1W H 0.019(4) 0.790(2) 0.150(3) 0.175 Uiso 1 1 d D U . . .
H2W H -0.004(5) 0.8654(12) 0.184(4) 0.175 Uiso 1 1 d D U . . .
O2W O -0.0648(3) 0.7981(2) -0.1111(3) 0.1387(11) Uani 1 1 d D . . . .
H3W H -0.086(5) 0.8435(18) -0.095(5) 0.208 Uiso 1 1 d D U . . .
H4W H -0.047(5) 0.768(3) -0.055(4) 0.208 Uiso 1 1 d D U . . .
O3W O -0.0595(4) 0.9542(4) -0.0605(5) 0.070(2) Uani 0.307(5) 1 d . . P D 1
O3WD O -0.0567(6) 0.9306(5) 0.1034(10) 0.075(4) Uani 0.193(5) 1 d . . P D 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.372(3) . ?
C1 C2 1.389(3) . ?
C1 Cl1 1.749(2) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.383(3) . ?
C3 C4 1.403(3) . ?
C4 C5 1.380(3) . ?
C4 N2 1.402(3) . ?
C5 C6 1.405(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.222(3) . ?
C7 N1 1.367(3) . ?
C7 N2 1.388(3) . ?
C8 N2 1.459(3) . ?
C8 C9 1.522(3) . ?
C8 C12 1.524(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.517(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N3 1.498(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.494(3) . ?
C11 C12 1.509(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.491(3) . ?
C13 C14 1.519(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N4 1.451(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.232(3) . ?
C16 N5 1.364(3) . ?
C16 N4 1.370(3) . ?
C17 C18 1.376(4) . ?
C17 N5 1.387(3) . ?
C17 C22 1.400(3) . ?
C18 C19 1.377(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(4) . ?
C21 H21 0.9300 . ?
C22 N4 1.394(3) . ?
N1 H1N 0.8600 . ?
N3 H3N 0.98(3) . ?
N5 H5N 0.8600 . ?
C23 C24 1.264(8) . ?
C23 N6 1.316(4) . ?
C23 C24D 1.532(12) . ?
C23 H23 0.9300 . ?
C28 C26D 1.177(7) . ?
C28 N6 1.327(4) . ?
C28 C26 1.515(6) . ?
C28 H28 0.9300 . ?
C24 C25 1.378(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.388(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.490(6) . ?
C27 O4 1.245(5) . ?
C27 O3 1.265(8) . ?
C24D C25D 1.374(11) . ?
C24D H24D 0.9300 . ?
C25D C26D 1.357(10) . ?
C25D H25D 0.9300 . ?
C26D C27D 1.470(8) . ?
C27D O3D 1.216(14) . ?
C27D O4D 1.280(14) . ?
O1W H1W 0.856(10) . ?
O1W H2W 0.855(10) . ?
O2W H3W 0.872(10) . ?
O2W H4W 0.877(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.8(2) . . ?
C6 C1 Cl1 119.06(19) . . ?
C2 C1 Cl1 118.15(18) . . ?
C3 C2 C1 116.5(2) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
C2 C3 N1 130.7(2) . . ?
C2 C3 C4 122.2(2) . . ?
N1 C3 C4 107.13(19) . . ?
C5 C4 N2 133.2(2) . . ?
C5 C4 C3 120.3(2) . . ?
N2 C4 C3 106.46(18) . . ?
C4 C5 C6 117.9(2) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 120.2(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O1 C7 N1 127.1(2) . . ?
O1 C7 N2 126.3(2) . . ?
N1 C7 N2 106.5(2) . . ?
N2 C8 C9 112.03(18) . . ?
N2 C8 C12 113.91(18) . . ?
C9 C8 C12 109.63(18) . . ?
N2 C8 H8 107.0 . . ?
C9 C8 H8 107.0 . . ?
C12 C8 H8 107.0 . . ?
C10 C9 C8 109.7(2) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N3 C10 C9 111.59(18) . . ?
N3 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N3 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
N3 C11 C12 111.55(18) . . ?
N3 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C8 110.7(2) . . ?
C11 C12 H12A 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N3 C13 C14 114.40(19) . . ?
N3 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
N3 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 108.1(2) . . ?
C15 C14 H14A 110.1 . . ?
C13 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
N4 C15 C14 113.9(2) . . ?
N4 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
N4 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O2 C16 N5 126.7(2) . . ?
O2 C16 N4 126.4(2) . . ?
N5 C16 N4 106.8(2) . . ?
C18 C17 N5 132.3(2) . . ?
C18 C17 C22 121.2(2) . . ?
N5 C17 C22 106.5(2) . . ?
C17 C18 C19 117.5(3) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
C18 C19 C20 121.7(3) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C21 121.0(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 117.4(3) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
C21 C22 N4 132.0(2) . . ?
C21 C22 C17 121.2(3) . . ?
N4 C22 C17 106.8(2) . . ?
C7 N1 C3 110.50(18) . . ?
C7 N1 H1N 124.8 . . ?
C3 N1 H1N 124.8 . . ?
C7 N2 C4 109.31(18) . . ?
C7 N2 C8 120.51(19) . . ?
C4 N2 C8 129.46(17) . . ?
C13 N3 C11 112.78(19) . . ?
C13 N3 C10 109.33(17) . . ?
C11 N3 C10 110.83(18) . . ?
C13 N3 H3N 105.7(15) . . ?
C11 N3 H3N 111.0(15) . . ?
C10 N3 H3N 106.9(15) . . ?
C16 N4 C22 109.56(19) . . ?
C16 N4 C15 124.2(2) . . ?
C22 N4 C15 125.9(2) . . ?
C16 N5 C17 110.3(2) . . ?
C16 N5 H5N 124.9 . . ?
C17 N5 H5N 124.9 . . ?
C24 C23 N6 131.3(4) . . ?
N6 C23 C24D 112.0(5) . . ?
C24 C23 H23 114.4 . . ?
N6 C23 H23 114.4 . . ?
C26D C28 N6 140.4(5) . . ?
N6 C28 C26 117.6(3) . . ?
N6 C28 H28 121.2 . . ?
C26 C28 H28 121.2 . . ?
C23 C24 C25 117.2(6) . . ?
C23 C24 H24 121.4 . . ?
C25 C24 H24 121.4 . . ?
C24 C25 C26 119.0(5) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C27 120.1(5) . . ?
C25 C26 C28 117.6(4) . . ?
C27 C26 C28 122.2(5) . . ?
O4 C27 O3 123.4(5) . . ?
O4 C27 C26 119.7(5) . . ?
O3 C27 C26 116.9(5) . . ?
C25D C24D C23 117.7(8) . . ?
C25D C24D H24D 121.1 . . ?
C23 C24D H24D 121.1 . . ?
C26D C25D C24D 124.4(8) . . ?
C26D C25D H25D 117.8 . . ?
C24D C25D H25D 117.8 . . ?
C28 C26D C25D 108.2(7) . . ?
C28 C26D C27D 125.8(8) . . ?
C25D C26D C27D 126.0(8) . . ?
O3D C27D O4D 126.5(8) . . ?
O3D C27D C26D 118.3(9) . . ?
O4D C27D C26D 115.2(9) . . ?
C23 N6 C28 116.8(2) . . ?
H1W O1W H2W 112(3) . . ?
H3W O2W H4W 118(3) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.6(3) . . . . ?
Cl1 C1 C2 C3 -178.58(15) . . . . ?
C1 C2 C3 N1 177.9(2) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
N1 C3 C4 C5 -178.70(19) . . . . ?
C2 C3 C4 N2 179.72(18) . . . . ?
N1 C3 C4 N2 0.7(2) . . . . ?
N2 C4 C5 C6 -178.8(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
Cl1 C1 C6 C5 179.35(17) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
N2 C8 C9 C10 175.00(19) . . . . ?
C12 C8 C9 C10 -57.5(3) . . . . ?
C8 C9 C10 N3 57.7(3) . . . . ?
N3 C11 C12 C8 -56.7(3) . . . . ?
N2 C8 C12 C11 -176.22(19) . . . . ?
C9 C8 C12 C11 57.4(3) . . . . ?
N3 C13 C14 C15 157.5(2) . . . . ?
C13 C14 C15 N4 175.7(2) . . . . ?
N5 C17 C18 C19 -178.8(2) . . . . ?
C22 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C18 C19 C20 C21 -0.8(5) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C20 C21 C22 N4 178.0(2) . . . . ?
C20 C21 C22 C17 0.0(4) . . . . ?
C18 C17 C22 C21 -0.2(3) . . . . ?
N5 C17 C22 C21 178.8(2) . . . . ?
C18 C17 C22 N4 -178.7(2) . . . . ?
N5 C17 C22 N4 0.3(2) . . . . ?
O1 C7 N1 C3 177.0(2) . . . . ?
N2 C7 N1 C3 -2.6(2) . . . . ?
C2 C3 N1 C7 -177.7(2) . . . . ?
C4 C3 N1 C7 1.1(2) . . . . ?
O1 C7 N2 C4 -176.6(2) . . . . ?
N1 C7 N2 C4 3.0(2) . . . . ?
O1 C7 N2 C8 -5.4(3) . . . . ?
N1 C7 N2 C8 174.15(18) . . . . ?
C5 C4 N2 C7 177.0(2) . . . . ?
C3 C4 N2 C7 -2.3(2) . . . . ?
C5 C4 N2 C8 6.9(4) . . . . ?
C3 C4 N2 C8 -172.43(19) . . . . ?
C9 C8 N2 C7 -109.5(2) . . . . ?
C12 C8 N2 C7 125.4(2) . . . . ?
C9 C8 N2 C4 59.7(3) . . . . ?
C12 C8 N2 C4 -65.5(3) . . . . ?
C14 C13 N3 C11 57.6(3) . . . . ?
C14 C13 N3 C10 -178.6(2) . . . . ?
C12 C11 N3 C13 178.7(2) . . . . ?
C12 C11 N3 C10 55.8(3) . . . . ?
C9 C10 N3 C13 178.5(2) . . . . ?
C9 C10 N3 C11 -56.5(3) . . . . ?
O2 C16 N4 C22 178.4(2) . . . . ?
N5 C16 N4 C22 -2.1(3) . . . . ?
O2 C16 N4 C15 4.5(4) . . . . ?
N5 C16 N4 C15 -176.0(2) . . . . ?
C21 C22 N4 C16 -177.2(3) . . . . ?
C17 C22 N4 C16 1.1(2) . . . . ?
C21 C22 N4 C15 -3.4(4) . . . . ?
C17 C22 N4 C15 174.9(2) . . . . ?
C14 C15 N4 C16 -105.0(3) . . . . ?
C14 C15 N4 C22 82.1(3) . . . . ?
O2 C16 N5 C17 -178.2(2) . . . . ?
N4 C16 N5 C17 2.3(3) . . . . ?
C18 C17 N5 C16 177.2(2) . . . . ?
C22 C17 N5 C16 -1.6(2) . . . . ?
N6 C23 C24 C25 3.9(9) . . . . ?
C23 C24 C25 C26 2.3(9) . . . . ?
C24 C25 C26 C27 -179.9(5) . . . . ?
C24 C25 C26 C28 -3.2(8) . . . . ?
N6 C28 C26 C25 -1.2(6) . . . . ?
N6 C28 C26 C27 175.4(4) . . . . ?
C25 C26 C27 O4 23.1(7) . . . . ?
C28 C26 C27 O4 -153.4(4) . . . . ?
C25 C26 C27 O3 -158.3(6) . . . . ?
C28 C26 C27 O3 25.2(7) . . . . ?
N6 C23 C24D C25D -2.3(12) . . . . ?
C23 C24D C25D C26D 0.4(16) . . . . ?
N6 C28 C26D C25D 6.8(12) . . . . ?
N6 C28 C26D C27D -173.3(8) . . . . ?
C24D C25D C26D C28 -1.7(14) . . . . ?
C24D C25D C26D C27D 178.5(12) . . . . ?
C28 C26D C27D O3D 11.3(18) . . . . ?
C25D C26D C27D O3D -168.9(11) . . . . ?
C28 C26D C27D O4D -168.8(9) . . . . ?
C25D C26D C27D O4D 11.1(17) . . . . ?
C24 C23 N6 C28 -8.5(6) . . . . ?
C24D C23 N6 C28 5.2(7) . . . . ?
C26D C28 N6 C23 -9.3(9) . . . . ?
C26 C28 N6 C23 6.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N N6 0.86 1.98 2.830(3) 169.5 2_656 yes
N3 H3N O3^a 0.98(3) 1.76(3) 2.735(5) 172(2) . yes
N3 H3N O3D^b 0.98(3) 2.57(3) 3.414(7) 144(2) . yes
N3 H3N O4D^b 0.98(3) 1.57(3) 2.498(7) 156(2) . yes
N5 H5N O1W 0.86 2.05 2.821(3) 149.3 4_575 yes
O1W H2W O4^a 0.855(10) 2.46(5) 3.085(5) 131(6) 2 yes
O1W H1W O2 0.856(10) 1.959(14) 2.804(3) 169(5) . yes
O2W H3W O3W^a 0.872(10) 2.01(4) 2.792(8) 149(7) . yes
O2W H4W O2 0.877(10) 2.10(4) 2.851(4) 144(7) . yes

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB719_0m
_database_code_depnum_ccdc_archive 'CCDC 2240376'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-09-26 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Domperidone aspirin'
_chemical_name_common            'Domperidone aspirin'
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 Cl N5 O2 1+, C9 H7 O4 1-'
_chemical_formula_sum            'C31 H32 Cl N5 O6'
_chemical_formula_weight         606.06

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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7232(2)
_cell_length_b                   9.5010(2)
_cell_length_c                   31.7204(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.0116(7)
_cell_angle_gamma                90
_cell_volume                     2928.53(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      29.87

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            39402
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.238
_diffrn_reflns_theta_max         30.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8629
_reflns_number_gt                5851
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+1.1015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8629
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1508
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.25426(19) 1.23633(17) 0.26785(5) 0.0679(5) Uani 1 1 d . . . . .
O3 O 0.38922(12) 0.76170(13) 0.40370(4) 0.0402(3) Uani 1 1 d . . . . .
O4 O 0.49453(14) 0.74153(16) 0.34300(4) 0.0497(3) Uani 1 1 d . . . . .
O5 O 0.71308(14) 0.94167(15) 0.34367(4) 0.0492(3) Uani 1 1 d . . . . .
O6 O 0.52327(19) 1.07101(19) 0.35545(5) 0.0738(5) Uani 1 1 d . . . . .
N2 N 0.28946(15) 0.26552(14) 0.41340(5) 0.0359(3) Uani 1 1 d . . . . .
C2 C 0.58489(18) 0.12807(18) 0.46867(5) 0.0370(4) Uani 1 1 d . . . . .
H2 H 0.615597 0.038841 0.476533 0.044 Uiso 1 1 calc R U . . .
N3 N 0.17176(15) 0.66047(14) 0.35890(4) 0.0312(3) Uani 1 1 d . . . . .
H3N H 0.245(2) 0.698(2) 0.3714(6) 0.039(5) Uiso 1 1 d . . . . .
C3 C 0.46039(17) 0.14814(16) 0.44712(5) 0.0321(3) Uani 1 1 d . . . . .
N4 N 0.15280(16) 1.02485(16) 0.24658(4) 0.0404(3) Uani 1 1 d . . . . .
C4 C 0.41496(17) 0.28337(17) 0.43521(5) 0.0321(3) Uani 1 1 d . . . . .
N5 N 0.28901(18) 1.13186(18) 0.20267(5) 0.0481(4) Uani 1 1 d . . . . .
H5N H 0.352(3) 1.196(3) 0.1908(8) 0.066(7) Uiso 1 1 d . . . . .
C5 C 0.49220(18) 0.40100(17) 0.44574(5) 0.0370(4) Uani 1 1 d . . . . .
H5 H 0.461240 0.490689 0.438481 0.044 Uiso 1 1 calc R U . . .
C6 C 0.61739(19) 0.38185(18) 0.46747(5) 0.0395(4) Uani 1 1 d . . . . .
H6 H 0.671448 0.459255 0.474960 0.047 Uiso 1 1 calc R U . . .
C7 C 0.25787(18) 0.12329(17) 0.41067(5) 0.0354(4) Uani 1 1 d . . . . .
C8 C 0.21213(18) 0.37132(17) 0.38890(5) 0.0360(4) Uani 1 1 d . . . . .
H8 H 0.133003 0.323887 0.375197 0.043 Uiso 1 1 calc R U . . .
C9 C 0.29793(19) 0.43357(18) 0.35428(5) 0.0376(4) Uani 1 1 d . . . . .
H9A H 0.381878 0.473000 0.366773 0.045 Uiso 1 1 calc R U . . .
H9B H 0.323374 0.359409 0.335038 0.045 Uiso 1 1 calc R U . . .
C10 C 0.22010(19) 0.54766(18) 0.32980(5) 0.0371(4) Uani 1 1 d . . . . .
H10A H 0.279633 0.588820 0.309219 0.044 Uiso 1 1 calc R U . . .
H10B H 0.141474 0.506401 0.314735 0.044 Uiso 1 1 calc R U . . .
C22 C 0.24429(18) 1.00974(19) 0.18285(6) 0.0397(4) Uani 1 1 d . . . . .
C11 C 0.08152(17) 0.59900(19) 0.39134(6) 0.0380(4) Uani 1 1 d . . . . .
H11A H 0.000386 0.558329 0.377473 0.046 Uiso 1 1 calc R U . . .
H11B H 0.051600 0.673127 0.409946 0.046 Uiso 1 1 calc R U . . .
C12 C 0.15632(18) 0.48645(18) 0.41720(5) 0.0393(4) Uani 1 1 d . . . . .
H12A H 0.093621 0.445137 0.436849 0.047 Uiso 1 1 calc R U . . .
H12B H 0.231858 0.529014 0.433411 0.047 Uiso 1 1 calc R U . . .
C13 C 0.09677(19) 0.77825(18) 0.33662(6) 0.0392(4) Uani 1 1 d . . . . .
H13A H 0.067396 0.845487 0.357488 0.047 Uiso 1 1 calc R U . . .
H13B H 0.014758 0.740463 0.322480 0.047 Uiso 1 1 calc R U . . .
C20 C 0.2056(2) 0.8284(2) 0.13300(7) 0.0567(5) Uani 1 1 d . . . . .
H20 H 0.222223 0.787230 0.107077 0.068 Uiso 1 1 calc R U . . .
Cl1 Cl 0.82225(6) 0.22786(6) 0.50327(2) 0.06282(17) Uani 1 1 d . . . . .
O1 O 0.15751(13) 0.07144(13) 0.39206(5) 0.0476(3) Uani 1 1 d . . . . .
N1 N 0.35991(15) 0.05420(15) 0.43337(5) 0.0359(3) Uani 1 1 d . . . . .
H1N H 0.370(2) -0.031(2) 0.4316(6) 0.044(6) Uiso 1 1 d . . . . .
C21 C 0.2701(2) 0.9531(2) 0.14390(6) 0.0514(5) Uani 1 1 d . . . . .
H21 H 0.328907 0.997454 0.125604 0.062 Uiso 1 1 calc R U . . .
C14 C 0.1800(2) 0.8545(2) 0.30471(6) 0.0452(4) Uani 1 1 d . . . . .
H14A H 0.203623 0.790250 0.282338 0.054 Uiso 1 1 calc R U . . .
H14B H 0.264815 0.888670 0.318096 0.054 Uiso 1 1 calc R U . . .
C15 C 0.0982(2) 0.9781(2) 0.28612(6) 0.0454(4) Uani 1 1 d . . . . .
H15A H 0.002915 0.950224 0.281519 0.054 Uiso 1 1 calc R U . . .
H15B H 0.100824 1.055531 0.306070 0.054 Uiso 1 1 calc R U . . .
C19 C 0.1166(2) 0.7635(2) 0.15995(7) 0.0535(5) Uani 1 1 d . . . . .
H19 H 0.073361 0.680286 0.151537 0.064 Uiso 1 1 calc R U . . .
C18 C 0.0903(2) 0.8193(2) 0.19913(6) 0.0448(4) Uani 1 1 d . . . . .
H18 H 0.030163 0.775530 0.217136 0.054 Uiso 1 1 calc R U . . .
C16 C 0.2360(2) 1.1420(2) 0.24183(6) 0.0450(4) Uani 1 1 d . . . . .
C1 C 0.66149(18) 0.24758(19) 0.47793(5) 0.0387(4) Uani 1 1 d . . . . .
C17 C 0.15661(17) 0.94204(18) 0.21038(5) 0.0355(4) Uani 1 1 d . . . . .
C24 C 0.7734(2) 0.8009(2) 0.46719(7) 0.0480(5) Uani 1 1 d . . . . .
H24 H 0.790912 0.765782 0.494216 0.058 Uiso 1 1 calc R U . . .
C25 C 0.65211(19) 0.76743(18) 0.44538(6) 0.0401(4) Uani 1 1 d . . . . .
H25 H 0.586494 0.713248 0.458537 0.048 Uiso 1 1 calc R U . . .
C26 C 0.62604(17) 0.81318(17) 0.40411(5) 0.0348(4) Uani 1 1 d . . . . .
C27 C 0.72522(18) 0.89796(19) 0.38575(6) 0.0392(4) Uani 1 1 d . . . . .
C28 C 0.6038(2) 1.0266(2) 0.33127(7) 0.0543(5) Uani 1 1 d . . . . .
C29 C 0.6023(3) 1.0526(4) 0.28487(8) 0.0835(8) Uani 1 1 d . . . . .
H29A H 0.553638 0.977754 0.270509 0.125 Uiso 1 1 calc R U . . .
H29B H 0.695131 1.056147 0.275553 0.125 Uiso 1 1 calc R U . . .
H29C H 0.557275 1.140450 0.278703 0.125 Uiso 1 1 calc R U . . .
C30 C 0.49425(17) 0.76991(17) 0.38128(5) 0.0346(3) Uani 1 1 d . . . . .
C31 C 0.86873(19) 0.8871(2) 0.44842(7) 0.0501(5) Uani 1 1 d . . . . .
H31 H 0.949536 0.911768 0.463157 0.060 Uiso 1 1 calc R U . . .
C32 C 0.84415(18) 0.9364(2) 0.40809(7) 0.0465(4) Uani 1 1 d . . . . .
H32 H 0.907551 0.995546 0.395810 0.056 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C16 1.227(2) . ?
O3 C30 1.267(2) . ?
O4 C30 1.244(2) . ?
O5 C28 1.381(3) . ?
O5 C27 1.399(2) . ?
O6 C28 1.192(3) . ?
N2 C7 1.388(2) . ?
N2 C4 1.392(2) . ?
N2 C8 1.462(2) . ?
C2 C3 1.382(2) . ?
C2 C1 1.384(3) . ?
C2 H2 0.9300 . ?
N3 C11 1.494(2) . ?
N3 C13 1.499(2) . ?
N3 C10 1.501(2) . ?
N3 H3N 0.88(2) . ?
C3 N1 1.383(2) . ?
C3 C4 1.406(2) . ?
N4 C16 1.387(2) . ?
N4 C17 1.394(2) . ?
N4 C15 1.449(2) . ?
C4 C5 1.381(2) . ?
N5 C16 1.365(2) . ?
N5 C22 1.382(2) . ?
N5 H5N 0.95(3) . ?
C5 C6 1.390(2) . ?
C5 H5 0.9300 . ?
C6 C1 1.383(2) . ?
C6 H6 0.9300 . ?
C7 O1 1.226(2) . ?
C7 N1 1.372(2) . ?
C8 C9 1.522(2) . ?
C8 C12 1.527(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.520(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C22 C21 1.379(3) . ?
C22 C17 1.398(2) . ?
C11 C12 1.518(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.504(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C20 C21 1.379(3) . ?
C20 C19 1.383(3) . ?
C20 H20 0.9300 . ?
Cl1 C1 1.7425(18) . ?
N1 H1N 0.82(2) . ?
C21 H21 0.9300 . ?
C14 C15 1.525(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C19 C18 1.383(3) . ?
C19 H19 0.9300 . ?
C18 C17 1.373(3) . ?
C18 H18 0.9300 . ?
C24 C25 1.383(3) . ?
C24 C31 1.387(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.394(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.399(2) . ?
C26 C30 1.507(2) . ?
C27 C32 1.384(3) . ?
C28 C29 1.492(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 C32 1.375(3) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C28 O5 C27 118.91(15) . . ?
C7 N2 C4 109.74(13) . . ?
C7 N2 C8 121.85(14) . . ?
C4 N2 C8 127.29(13) . . ?
C3 C2 C1 116.57(15) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
C11 N3 C13 109.19(13) . . ?
C11 N3 C10 110.40(13) . . ?
C13 N3 C10 113.64(13) . . ?
C11 N3 H3N 109.7(12) . . ?
C13 N3 H3N 106.4(13) . . ?
C10 N3 H3N 107.4(12) . . ?
C2 C3 N1 131.59(15) . . ?
C2 C3 C4 121.35(15) . . ?
N1 C3 C4 107.06(14) . . ?
C16 N4 C17 109.34(14) . . ?
C16 N4 C15 124.93(16) . . ?
C17 N4 C15 124.16(15) . . ?
C5 C4 N2 132.74(15) . . ?
C5 C4 C3 120.76(15) . . ?
N2 C4 C3 106.49(14) . . ?
C16 N5 C22 110.51(16) . . ?
C16 N5 H5N 125.7(15) . . ?
C22 N5 H5N 123.7(15) . . ?
C4 C5 C6 118.26(15) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 119.92(16) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 N1 127.51(15) . . ?
O1 C7 N2 126.29(16) . . ?
N1 C7 N2 106.19(14) . . ?
N2 C8 C9 111.47(14) . . ?
N2 C8 C12 111.51(14) . . ?
C9 C8 C12 111.16(13) . . ?
N2 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C12 C8 H8 107.5 . . ?
C10 C9 C8 111.72(14) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 C9 110.88(13) . . ?
N3 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C21 C22 N5 132.14(17) . . ?
C21 C22 C17 120.93(18) . . ?
N5 C22 C17 106.92(15) . . ?
N3 C11 C12 111.45(13) . . ?
N3 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C8 111.13(14) . . ?
C11 C12 H12A 109.4 . . ?
C8 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C8 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N3 C13 C14 114.37(14) . . ?
N3 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
N3 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C21 C20 C19 121.16(19) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C7 N1 C3 110.28(14) . . ?
C7 N1 H1N 121.4(14) . . ?
C3 N1 H1N 125.4(14) . . ?
C20 C21 C22 117.68(18) . . ?
C20 C21 H21 121.2 . . ?
C22 C21 H21 121.2 . . ?
C13 C14 C15 110.22(15) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N4 C15 C14 111.65(15) . . ?
N4 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
N4 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C20 C19 C18 121.6(2) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C17 C18 C19 117.34(18) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
O2 C16 N5 127.83(19) . . ?
O2 C16 N4 125.76(18) . . ?
N5 C16 N4 106.40(16) . . ?
C6 C1 C2 123.10(16) . . ?
C6 C1 Cl1 118.40(14) . . ?
C2 C1 Cl1 118.50(14) . . ?
C18 C17 N4 131.88(16) . . ?
C18 C17 C22 121.28(16) . . ?
N4 C17 C22 106.81(15) . . ?
C25 C24 C31 119.46(19) . . ?
C25 C24 H24 120.3 . . ?
C31 C24 H24 120.3 . . ?
C24 C25 C26 121.45(17) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C27 117.73(16) . . ?
C25 C26 C30 119.33(15) . . ?
C27 C26 C30 122.94(16) . . ?
C32 C27 O5 116.83(16) . . ?
C32 C27 C26 120.95(17) . . ?
O5 C27 C26 122.14(16) . . ?
O6 C28 O5 122.7(2) . . ?
O6 C28 C29 126.3(2) . . ?
O5 C28 C29 111.0(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O4 C30 O3 124.34(16) . . ?
O4 C30 C26 119.83(15) . . ?
O3 C30 C26 115.81(15) . . ?
C32 C31 C24 120.22(18) . . ?
C32 C31 H31 119.9 . . ?
C24 C31 H31 119.9 . . ?
C31 C32 C27 120.11(18) . . ?
C31 C32 H32 119.9 . . ?
C27 C32 H32 119.9 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 N1 -179.52(17) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C7 N2 C4 C5 178.82(18) . . . . ?
C8 N2 C4 C5 10.9(3) . . . . ?
C7 N2 C4 C3 -1.39(18) . . . . ?
C8 N2 C4 C3 -169.34(15) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
N1 C3 C4 C5 178.07(15) . . . . ?
C2 C3 C4 N2 178.44(14) . . . . ?
N1 C3 C4 N2 -1.75(17) . . . . ?
N2 C4 C5 C6 -178.66(17) . . . . ?
C3 C4 C5 C6 1.6(2) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 N2 C7 O1 -176.90(17) . . . . ?
C8 N2 C7 O1 -8.2(3) . . . . ?
C4 N2 C7 N1 3.98(19) . . . . ?
C8 N2 C7 N1 172.71(14) . . . . ?
C7 N2 C8 C9 -109.67(17) . . . . ?
C4 N2 C8 C9 57.0(2) . . . . ?
C7 N2 C8 C12 125.45(17) . . . . ?
C4 N2 C8 C12 -67.9(2) . . . . ?
N2 C8 C9 C10 -177.77(13) . . . . ?
C12 C8 C9 C10 -52.69(19) . . . . ?
C11 N3 C10 C9 -58.24(18) . . . . ?
C13 N3 C10 C9 178.69(14) . . . . ?
C8 C9 C10 N3 55.67(19) . . . . ?
C16 N5 C22 C21 -179.4(2) . . . . ?
C16 N5 C22 C17 1.5(2) . . . . ?
C13 N3 C11 C12 -175.65(15) . . . . ?
C10 N3 C11 C12 58.73(19) . . . . ?
N3 C11 C12 C8 -55.9(2) . . . . ?
N2 C8 C12 C11 177.56(14) . . . . ?
C9 C8 C12 C11 52.51(19) . . . . ?
C11 N3 C13 C14 176.71(15) . . . . ?
C10 N3 C13 C14 -59.6(2) . . . . ?
O1 C7 N1 C3 175.76(17) . . . . ?
N2 C7 N1 C3 -5.14(18) . . . . ?
C2 C3 N1 C7 -175.88(17) . . . . ?
C4 C3 N1 C7 4.34(18) . . . . ?
C19 C20 C21 C22 0.9(3) . . . . ?
N5 C22 C21 C20 -178.5(2) . . . . ?
C17 C22 C21 C20 0.5(3) . . . . ?
N3 C13 C14 C15 -176.12(16) . . . . ?
C16 N4 C15 C14 -101.4(2) . . . . ?
C17 N4 C15 C14 62.8(2) . . . . ?
C13 C14 C15 N4 -161.05(17) . . . . ?
C21 C20 C19 C18 -1.1(3) . . . . ?
C20 C19 C18 C17 -0.2(3) . . . . ?
C22 N5 C16 O2 180.0(2) . . . . ?
C22 N5 C16 N4 -1.4(2) . . . . ?
C17 N4 C16 O2 179.4(2) . . . . ?
C15 N4 C16 O2 -14.4(3) . . . . ?
C17 N4 C16 N5 0.8(2) . . . . ?
C15 N4 C16 N5 166.93(16) . . . . ?
C5 C6 C1 C2 -1.6(3) . . . . ?
C5 C6 C1 Cl1 177.42(14) . . . . ?
C3 C2 C1 C6 1.4(3) . . . . ?
C3 C2 C1 Cl1 -177.58(12) . . . . ?
C19 C18 C17 N4 179.55(19) . . . . ?
C19 C18 C17 C22 1.7(3) . . . . ?
C16 N4 C17 C18 -177.97(19) . . . . ?
C15 N4 C17 C18 15.7(3) . . . . ?
C16 N4 C17 C22 0.1(2) . . . . ?
C15 N4 C17 C22 -166.16(16) . . . . ?
C21 C22 C17 C18 -1.9(3) . . . . ?
N5 C22 C17 C18 177.38(17) . . . . ?
C21 C22 C17 N4 179.78(17) . . . . ?
N5 C22 C17 N4 -0.97(19) . . . . ?
C31 C24 C25 C26 3.0(3) . . . . ?
C24 C25 C26 C27 -1.9(3) . . . . ?
C24 C25 C26 C30 178.03(16) . . . . ?
C28 O5 C27 C32 -120.35(19) . . . . ?
C28 O5 C27 C26 62.9(2) . . . . ?
C25 C26 C27 C32 -0.8(3) . . . . ?
C30 C26 C27 C32 179.29(16) . . . . ?
C25 C26 C27 O5 175.74(16) . . . . ?
C30 C26 C27 O5 -4.1(3) . . . . ?
C27 O5 C28 O6 4.4(3) . . . . ?
C27 O5 C28 C29 -175.5(2) . . . . ?
C25 C26 C30 O4 -142.34(17) . . . . ?
C27 C26 C30 O4 37.5(2) . . . . ?
C25 C26 C30 O3 35.9(2) . . . . ?
C27 C26 C30 O3 -144.26(16) . . . . ?
C25 C24 C31 C32 -1.5(3) . . . . ?
C24 C31 C32 C27 -1.2(3) . . . . ?
O5 C27 C32 C31 -174.42(17) . . . . ?
C26 C27 C32 C31 2.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5N O4 0.95(3) 1.92(3) 2.798(2) 153(2) 2_655 yes
N5 H5N O5 0.95(3) 2.65(3) 3.290(2) 125.5(18) 2_655 yes
N1 H1N O3 0.82(2) 2.17(2) 2.9510(19) 159.9(19) 1_545 yes
N3 H3N O3 0.88(2) 1.81(2) 2.6842(19) 171.7(18) . yes
N3 H3N O4 0.88(2) 2.646(19) 3.288(2) 130.5(15) . yes

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
