#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:14:52 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281431 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/60/7246092.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246092
loop_
_publ_author_name
'Rekha Rout, Smruti'
'Kenguva, Gowtham'
'Giri, Lopamudra'
'Dandela, Rambabu'
_publ_section_title
;
 Novel salts of the antiemetic drug domperidone: synthesis,
 characterization and physicochemical property investigation
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              513
_journal_page_last               524
_journal_paper_doi               10.1039/D2CE00902A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C22 H24 Cl N5 O2,0.5(C6 H8 O4),H2 O'
_chemical_formula_sum            'C25 H30 Cl N5 O5'
_chemical_formula_weight         515.99
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-30 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                102.40(5)
_cell_angle_beta                 113.18(4)
_cell_angle_gamma                108.06(5)
_cell_formula_units_Z            2
_cell_length_a                   11.189(1)
_cell_length_b                   11.669(1)
_cell_length_c                   12.054(2)
_cell_measurement_reflns_used    4206
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      0.965
_cell_measurement_theta_min      0.950
_cell_volume                     1269.3(11)
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture photon 100 CMOS detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            40021
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.408
_diffrn_reflns_theta_min         2.207
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             544.0
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.251
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.2464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1745
_refine_ls_wR_factor_ref         0.2038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4206
_reflns_number_total             5733
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00902a2.cif
_cod_data_source_block           DomAA_0m_a
_cod_depositor_comments
'Adding full bibliography for 7246090--7246098.cif.'
_cod_original_cell_volume        1269.3(1)
_cod_database_code               7246092
_shelx_shelxl_version_number     2018/3
_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'
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
Cl1 Cl -0.38841(7) 0.56839(7) -0.07965(7) 0.0720(3) Uani 1 1 d . . . . .
O2 O 0.24627(19) 1.01437(17) -0.07911(19) 0.0622(5) Uani 1 1 d . . . . .
O1 O 1.1719(2) 0.84797(18) 0.39248(19) 0.0717(5) Uani 1 1 d . . . . .
N3 N 0.5875(2) 0.84900(17) 0.25477(17) 0.0430(4) Uani 1 1 d . . . . .
N4 N 0.19348(19) 0.86583(17) 0.01560(18) 0.0446(4) Uani 1 1 d . . . . .
N5 N 0.0165(2) 0.90193(19) -0.1129(2) 0.0491(4) Uani 1 1 d . . . . .
O4 O 0.3680(3) 0.6731(2) 0.3291(2) 0.0786(6) Uani 1 1 d . . . . .
N2 N 0.9672(2) 0.69251(19) 0.3724(2) 0.0550(5) Uani 1 1 d . . . . .
N1 N 1.1215(2) 0.6289(2) 0.3430(2) 0.0558(5) Uani 1 1 d . . . . .
O3 O 0.6004(3) 0.7602(2) 0.4471(3) 0.0934(7) Uani 1 1 d . . . . .
C22 C 0.0669(2) 0.7851(2) 0.00883(19) 0.0417(4) Uani 1 1 d . . . . .
C16 C 0.1604(2) 0.9367(2) -0.0614(2) 0.0467(5) Uani 1 1 d . . . . .
C14 C 0.3500(2) 0.7502(2) 0.0502(2) 0.0463(5) Uani 1 1 d . . . . .
H14A H 0.302744 0.694805 0.084324 0.056 Uiso 1 1 calc R U . . .
H14B H 0.301383 0.705072 -0.044012 0.056 Uiso 1 1 calc R U . . .
C17 C -0.0441(2) 0.8090(2) -0.0722(2) 0.0429(4) Uani 1 1 d . . . . .
C1 C 0.9134(3) 0.5585(2) 0.3466(2) 0.0508(5) Uani 1 1 d . . . . .
C21 C 0.0383(3) 0.6936(2) 0.0629(2) 0.0520(5) Uani 1 1 d . . . . .
H21 H 0.111703 0.677207 0.116862 0.062 Uiso 1 1 calc R U . . .
C18 C -0.1863(2) 0.7446(2) -0.1006(2) 0.0495(5) Uani 1 1 d . . . . .
C15 C 0.5077(2) 0.7762(2) 0.1095(2) 0.0459(5) Uani 1 1 d . . . . .
H15A H 0.513895 0.693842 0.089817 0.055 Uiso 1 1 calc R U . . .
H15B H 0.552885 0.826835 0.070803 0.055 Uiso 1 1 calc R U . . .
O7 O 0.8374(4) 0.9458(3) 0.6843(3) 0.1123(11) Uani 1 1 d . . . . .
C13 C 0.3395(2) 0.8784(2) 0.0829(2) 0.0449(5) Uani 1 1 d . . . . .
H13 H 0.395957 0.933732 0.053649 0.054 Uiso 1 1 calc R U . . .
C20 C -0.1045(3) 0.6267(2) 0.0335(2) 0.0553(6) Uani 1 1 d . . . . .
H20 H -0.127304 0.564097 0.067653 0.066 Uiso 1 1 calc R U . . .
C19 C -0.2117(2) 0.6531(2) -0.0457(2) 0.0515(5) Uani 1 1 d . . . . .
C6 C 1.0130(3) 0.5197(2) 0.3288(2) 0.0500(5) Uani 1 1 d . . . . .
C10 C 0.7442(2) 0.8801(2) 0.3152(2) 0.0549(6) Uani 1 1 d . . . . .
H10A H 0.790269 0.926706 0.408855 0.066 Uiso 1 1 calc R U . . .
H10B H 0.788989 0.937517 0.281070 0.066 Uiso 1 1 calc R U . . .
C23 C 0.4777(3) 0.6994(2) 0.4299(3) 0.0588(6) Uani 1 1 d . . . . .
C12 C 0.4135(3) 0.9463(2) 0.2306(2) 0.0531(5) Uani 1 1 d . . . . .
H12A H 0.406577 1.028045 0.252804 0.064 Uiso 1 1 calc R U . . .
H12B H 0.365921 0.891555 0.265055 0.064 Uiso 1 1 calc R U . . .
C11 C 0.5711(3) 0.9723(2) 0.2908(2) 0.0552(6) Uani 1 1 d . . . . .
H11A H 0.619691 1.032589 0.261186 0.066 Uiso 1 1 calc R U . . .
H11B H 0.617157 1.013185 0.385199 0.066 Uiso 1 1 calc R U . . .
C24 C 0.4665(3) 0.6541(3) 0.5361(3) 0.0592(6) Uani 1 1 d . . . . .
H24A H 0.514663 0.729612 0.617039 0.071 Uiso 1 1 calc R U . . .
H24B H 0.365307 0.611226 0.511543 0.071 Uiso 1 1 calc R U . . .
C7 C 1.0958(3) 0.7351(2) 0.3717(2) 0.0549(6) Uani 1 1 d . . . . .
C5 C 0.9947(3) 0.3921(3) 0.3060(2) 0.0615(6) Uani 1 1 d . . . . .
H5 H 1.060897 0.365843 0.294502 0.074 Uiso 1 1 calc R U . . .
C2 C 0.7932(3) 0.4718(3) 0.3398(3) 0.0624(6) Uani 1 1 d . . . . .
H2 H 0.726064 0.497364 0.349978 0.075 Uiso 1 1 calc R U . . .
C9 C 0.7710(3) 0.7591(3) 0.2893(3) 0.0646(7) Uani 1 1 d . . . . .
H9A H 0.689596 0.684207 0.275020 0.078 Uiso 1 1 calc R U . . .
H9B H 0.779448 0.741498 0.211060 0.078 Uiso 1 1 calc R U . . .
C8 C 0.9071(3) 0.7794(3) 0.4034(2) 0.0629(7) Uani 1 1 d . . . . .
H8A H 0.978864 0.868792 0.436859 0.075 Uiso 1 1 calc R U . . .
H8B H 0.886671 0.767488 0.472319 0.075 Uiso 1 1 calc R U . . .
C3 C 0.7753(4) 0.3448(3) 0.3173(3) 0.0701(8) Uani 1 1 d . . . . .
H3 H 0.694846 0.284077 0.312796 0.084 Uiso 1 1 calc R U . . .
C4 C 0.8744(4) 0.3059(3) 0.3012(3) 0.0684(8) Uani 1 1 d . . . . .
H4 H 0.859547 0.219870 0.286925 0.082 Uiso 1 1 calc R U . . .
C25 C 0.5335(4) 0.5609(3) 0.5585(3) 0.0730(8) Uani 1 1 d . . . . .
H25A H 0.635616 0.605846 0.587014 0.088 Uiso 1 1 calc R U . . .
H25B H 0.525713 0.537354 0.628612 0.088 Uiso 1 1 calc R U . . .
H100 H 0.555(3) 0.800(2) 0.292(2) 0.045(6) Uiso 1 1 d . . . . .
H101 H -0.030(3) 0.924(3) -0.172(3) 0.058(7) Uiso 1 1 d . . . . .
H102 H 0.845(4) 1.013(4) 0.671(4) 0.099(12) Uiso 1 1 d . . . . .
H103 H 0.770(7) 0.882(7) 0.624(7) 0.19(3) Uiso 1 1 d . . . . .
H104 H 1.202(3) 0.639(3) 0.339(3) 0.071(9) Uiso 1 1 d . . . . .
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'
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
C10 N3 C15 112.45(18) . . ?
C10 N3 C11 109.62(17) . . ?
C15 N3 C11 111.44(17) . . ?
C16 N4 C22 108.86(17) . . ?
C16 N4 C13 120.98(17) . . ?
C22 N4 C13 130.11(17) . . ?
C16 N5 C17 110.13(19) . . ?
C7 N2 C1 109.6(2) . . ?
C7 N2 C8 122.7(2) . . ?
C1 N2 C8 127.6(2) . . ?
C7 N1 C6 110.2(2) . . ?
C21 C22 N4 132.7(2) . . ?
C21 C22 C17 120.69(19) . . ?
N4 C22 C17 106.63(17) . . ?
O2 C16 N5 127.4(2) . . ?
O2 C16 N4 125.5(2) . . ?
N5 C16 N4 107.04(18) . . ?
C15 C14 C13 109.70(17) . . ?
N5 C17 C18 130.6(2) . . ?
N5 C17 C22 107.33(18) . . ?
C18 C17 C22 122.10(19) . . ?
C2 C1 C6 121.3(2) . . ?
C2 C1 N2 132.6(2) . . ?
C6 C1 N2 106.1(2) . . ?
C22 C21 C20 117.8(2) . . ?
C19 C18 C17 115.9(2) . . ?
N3 C15 C14 111.30(18) . . ?
N4 C13 C14 113.99(17) . . ?
N4 C13 C12 113.26(19) . . ?
C14 C13 C12 108.96(17) . . ?
C19 C20 C21 120.4(2) . . ?
C20 C19 C18 123.2(2) . . ?
C20 C19 Cl1 119.14(18) . . ?
C18 C19 Cl1 117.66(19) . . ?
N1 C6 C5 131.7(2) . . ?
N1 C6 C1 107.3(2) . . ?
C5 C6 C1 121.0(2) . . ?
N3 C10 C9 113.1(2) . . ?
O4 C23 O3 121.6(2) . . ?
O4 C23 C24 120.5(2) . . ?
O3 C23 C24 117.9(3) . . ?
C11 C12 C13 109.5(2) . . ?
N3 C11 C12 111.77(18) . . ?
C25 C24 C23 112.3(2) . . ?
O1 C7 N1 127.1(3) . . ?
O1 C7 N2 126.1(2) . . ?
N1 C7 N2 106.8(2) . . ?
C4 C5 C6 117.2(3) . . ?
C1 C2 C3 117.6(3) . . ?
C8 C9 C10 110.3(2) . . ?
N2 C8 C9 114.0(2) . . ?
C2 C3 C4 121.5(3) . . ?
C5 C4 C3 121.4(3) . . ?
C25 C25 C24 114.4(3) 2_666 . ?
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
Cl1 C19 1.741(2) . ?
O2 C16 1.222(3) . ?
O1 C7 1.232(3) . ?
N3 C10 1.491(3) . ?
N3 C15 1.498(3) . ?
N3 C11 1.501(3) . ?
N4 C16 1.390(3) . ?
N4 C22 1.396(2) . ?
N4 C13 1.451(3) . ?
N5 C16 1.357(3) . ?
N5 C17 1.382(3) . ?
O4 C23 1.228(3) . ?
N2 C7 1.373(3) . ?
N2 C1 1.402(3) . ?
N2 C8 1.442(3) . ?
N1 C7 1.362(3) . ?
N1 C6 1.383(3) . ?
O3 C23 1.241(3) . ?
C22 C21 1.385(3) . ?
C22 C17 1.398(3) . ?
C14 C15 1.516(3) . ?
C14 C13 1.517(3) . ?
C17 C18 1.390(3) . ?
C1 C2 1.368(3) . ?
C1 C6 1.397(3) . ?
C21 C20 1.396(3) . ?
C18 C19 1.386(3) . ?
C13 C12 1.520(3) . ?
C20 C19 1.378(4) . ?
C6 C5 1.387(3) . ?
C10 C9 1.526(4) . ?
C23 C24 1.519(3) . ?
C12 C11 1.514(3) . ?
C24 C25 1.514(4) . ?
C5 C4 1.379(4) . ?
C2 C3 1.382(4) . ?
C9 C8 1.501(3) . ?
C3 C4 1.384(4) . ?
C25 C25 1.488(6) 2_666 ?
