#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:14:52 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281431 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/60/7246093.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_7246093
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 H25 Cl N5 O2,0.5(C4 H4 O4),H2 O'
_chemical_formula_sum            'C24 H29 Cl N5 O5'
_chemical_formula_weight         502.97
_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                101.11(5)
_cell_angle_beta                 111.12(5)
_cell_angle_gamma                108.46(4)
_cell_formula_units_Z            2
_cell_length_a                   10.615(1)
_cell_length_b                   11.596(1)
_cell_length_c                   11.894(1)
_cell_measurement_reflns_used    4238
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      0.960
_cell_measurement_theta_min      0.952
_cell_volume                     1215.1(9)
_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 0.985
_diffrn_measured_fraction_theta_max 0.988
_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  0.0700
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_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            22623
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.247
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6141
_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    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             530.0
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0529P)²+0.5645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1420
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4238
_reflns_number_total             5513
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00902a2.cif
_cod_data_source_block           DomSuc_0m_a
_cod_depositor_comments
'Adding full bibliography for 7246090--7246098.cif.'
_cod_original_cell_volume        1215.2(3)
_cod_database_code               7246093
_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.
;
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.960
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 1.43268(7) 0.41957(6) 1.10767(7) 0.0701(2) Uani 1 1 d . . . . .
O1 O -0.20506(15) 0.15593(13) 0.60366(14) 0.0451(3) Uani 1 1 d . . . . .
O3 O 0.56545(16) 0.32094(15) 0.63922(16) 0.0516(4) Uani 1 1 d . . . . .
O2 O 0.73519(17) -0.01648(15) 1.08041(16) 0.0562(4) Uani 1 1 d . . . . .
N3 N 0.42089(16) 0.16129(14) 0.73510(15) 0.0340(3) Uani 1 1 d . . . . .
N2 N 0.01279(16) 0.31006(15) 0.62399(15) 0.0367(3) Uani 1 1 d . . . . .
N4 N 0.81176(17) 0.13192(16) 0.98592(16) 0.0400(4) Uani 1 1 d . . . . .
N1 N -0.15003(18) 0.37518(16) 0.65320(16) 0.0375(4) Uani 1 1 d . . . . .
O4 O 0.34374(18) 0.28516(16) 0.4917(2) 0.0703(5) Uani 1 1 d . . . . .
N5 N 0.98058(18) 0.08963(16) 1.12083(17) 0.0413(4) Uani 1 1 d . . . . .
O7 O 0.1430(3) 0.0421(2) 0.3272(2) 0.0810(7) Uani 1 1 d . . . . .
C1 C 0.0693(2) 0.44276(18) 0.64850(17) 0.0356(4) Uani 1 1 d . . . . .
C6 C -0.0341(2) 0.48393(18) 0.66692(17) 0.0352(4) Uani 1 1 d . . . . .
C7 C -0.12345(19) 0.26823(18) 0.62444(18) 0.0356(4) Uani 1 1 d . . . . .
C8 C 0.0771(2) 0.22279(19) 0.59163(19) 0.0403(4) Uani 1 1 d . . . . .
H8A H 0.093729 0.232213 0.518253 0.048 Uiso 1 1 calc R U . . .
H8B H 0.006216 0.134216 0.566629 0.048 Uiso 1 1 calc R U . . .
C17 C 1.0552(2) 0.18227(17) 1.08324(18) 0.0355(4) Uani 1 1 d . . . . .
C23 C 0.4795(2) 0.35025(19) 0.5552(2) 0.0419(5) Uani 1 1 d . . . . .
C22 C 0.9486(2) 0.21004(18) 0.99717(17) 0.0364(4) Uani 1 1 d . . . . .
C10 C 0.25904(19) 0.13183(18) 0.67115(19) 0.0367(4) Uani 1 1 d . . . . .
H10A H 0.205955 0.065594 0.696820 0.044 Uiso 1 1 calc R U . . .
H10B H 0.222150 0.096180 0.578916 0.044 Uiso 1 1 calc R U . . .
C16 C 0.8326(2) 0.05890(18) 1.06477(19) 0.0394(4) Uani 1 1 d . . . . .
C11 C 0.4385(2) 0.03791(17) 0.70445(19) 0.0390(4) Uani 1 1 d . . . . .
H11A H 0.400927 0.000778 0.612264 0.047 Uiso 1 1 calc R U . . .
H11B H 0.379219 -0.023359 0.730636 0.047 Uiso 1 1 calc R U . . .
C5 C -0.0117(2) 0.61212(19) 0.6898(2) 0.0455(5) Uani 1 1 d . . . . .
H5 H -0.080532 0.640129 0.701582 0.055 Uiso 1 1 calc R U . . .
C15 C 0.4929(2) 0.23312(19) 0.87603(18) 0.0394(4) Uani 1 1 d . . . . .
H15A H 0.437012 0.185674 0.913977 0.047 Uiso 1 1 calc R U . . .
H15B H 0.489821 0.317186 0.890226 0.047 Uiso 1 1 calc R U . . .
C13 C 0.6629(2) 0.12379(19) 0.91386(19) 0.0403(4) Uani 1 1 d . . . . .
H13 H 0.597809 0.068834 0.941714 0.048 Uiso 1 1 calc R U . . .
C12 C 0.5991(2) 0.0581(2) 0.7708(2) 0.0430(5) Uani 1 1 d . . . . .
H12A H 0.604663 -0.024965 0.753445 0.052 Uiso 1 1 calc R U . . .
H12B H 0.656954 0.111065 0.737541 0.052 Uiso 1 1 calc R U . . .
C14 C 0.6529(2) 0.25206(19) 0.94219(19) 0.0419(4) Uani 1 1 d . . . . .
H14A H 0.712244 0.308911 0.912639 0.050 Uiso 1 1 calc R U . . .
H14B H 0.692655 0.292747 1.034225 0.050 Uiso 1 1 calc R U . . .
C18 C 1.2049(2) 0.24477(19) 1.1188(2) 0.0429(5) Uani 1 1 d . . . . .
H18 H 1.275396 0.225606 1.175646 0.052 Uiso 1 1 calc R U . . .
C9 C 0.2231(2) 0.2469(2) 0.7011(2) 0.0446(5) Uani 1 1 d . . . . .
H9A H 0.302307 0.324878 0.711411 0.054 Uiso 1 1 calc R U . . .
H9B H 0.214811 0.258903 0.780707 0.054 Uiso 1 1 calc R U . . .
C19 C 1.2447(2) 0.3377(2) 1.0651(2) 0.0464(5) Uani 1 1 d . . . . .
C2 C 0.1976(2) 0.5278(2) 0.6533(2) 0.0463(5) Uani 1 1 d . . . . .
H2 H 0.266574 0.500220 0.641357 0.056 Uiso 1 1 calc R U . . .
C21 C 0.9909(2) 0.3027(2) 0.9443(2) 0.0477(5) Uani 1 1 d . . . . .
H21 H 0.920694 0.321551 0.886674 0.057 Uiso 1 1 calc R U . . .
C3 C 0.2193(2) 0.6556(2) 0.6766(2) 0.0523(5) Uani 1 1 d . . . . .
H3 H 0.304772 0.715199 0.680295 0.063 Uiso 1 1 calc R U . . .
C24 C 0.5515(2) 0.4765(2) 0.5393(2) 0.0501(5) Uani 1 1 d . . . . .
H24A H 0.614438 0.542505 0.624022 0.060 Uiso 1 1 calc R U . . .
H24B H 0.615647 0.467114 0.500646 0.060 Uiso 1 1 calc R U . . .
C20 C 1.1419(3) 0.3669(2) 0.9803(2) 0.0524(5) Uani 1 1 d . . . . .
H20 H 1.173726 0.430138 0.946711 0.063 Uiso 1 1 calc R U . . .
C4 C 0.1172(3) 0.6971(2) 0.6944(2) 0.0520(5) Uani 1 1 d . . . . .
H4 H 0.135494 0.783916 0.709916 0.062 Uiso 1 1 calc R U . . .
H100 H 0.474(3) 0.220(2) 0.698(2) 0.063(7) Uiso 1 1 d . . . . .
H101 H -0.232(3) 0.372(2) 0.657(2) 0.049(6) Uiso 1 1 d . . . . .
H102 H 1.016(3) 0.062(2) 1.175(3) 0.060(7) Uiso 1 1 d . . . . .
H103 H 0.221(3) 0.108(3) 0.364(3) 0.069(9) Uiso 1 1 d . . . . .
H104 H 0.160(4) -0.013(3) 0.336(3) 0.081(10) 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
C15 N3 C11 112.55(14) . . ?
C15 N3 C10 112.63(14) . . ?
C11 N3 C10 108.85(14) . . ?
C7 N2 C1 109.56(15) . . ?
C7 N2 C8 123.18(16) . . ?
C1 N2 C8 127.08(16) . . ?
C16 N4 C22 109.35(15) . . ?
C16 N4 C13 119.92(16) . . ?
C22 N4 C13 130.62(15) . . ?
C7 N1 C6 109.92(16) . . ?
C16 N5 C17 110.81(16) . . ?
C2 C1 N2 131.64(18) . . ?
C2 C1 C6 121.54(18) . . ?
N2 C1 C6 106.80(16) . . ?
C5 C6 N1 132.23(18) . . ?
C5 C6 C1 120.87(18) . . ?
N1 C6 C1 106.87(16) . . ?
O1 C7 N1 126.73(17) . . ?
O1 C7 N2 126.45(17) . . ?
N1 C7 N2 106.82(16) . . ?
N2 C8 C9 113.48(16) . . ?
N5 C17 C18 130.85(18) . . ?
N5 C17 C22 107.01(16) . . ?
C18 C17 C22 122.13(18) . . ?
O4 C23 O3 124.40(18) . . ?
O4 C23 C24 119.56(18) . . ?
O3 C23 C24 115.97(18) . . ?
C21 C22 N4 132.93(18) . . ?
C21 C22 C17 120.55(18) . . ?
N4 C22 C17 106.50(15) . . ?
N3 C10 C9 114.79(15) . . ?
O2 C16 N5 127.84(18) . . ?
O2 C16 N4 125.84(18) . . ?
N5 C16 N4 106.31(16) . . ?
N3 C11 C12 112.36(15) . . ?
C6 C5 C4 117.3(2) . . ?
N3 C15 C14 112.42(16) . . ?
N4 C13 C14 113.84(16) . . ?
N4 C13 C12 113.01(17) . . ?
C14 C13 C12 110.27(15) . . ?
C13 C12 C11 110.02(16) . . ?
C13 C14 C15 110.47(16) . . ?
C17 C18 C19 116.31(19) . . ?
C10 C9 C8 109.04(16) . . ?
C20 C19 C18 122.65(19) . . ?
C20 C19 Cl1 119.41(17) . . ?
C18 C19 Cl1 117.94(17) . . ?
C1 C2 C3 117.2(2) . . ?
C22 C21 C20 117.71(19) . . ?
C2 C3 C4 121.6(2) . . ?
C24 C24 C23 116.1(2) 2_666 . ?
C19 C20 C21 120.65(19) . . ?
C3 C4 C5 121.4(2) . . ?
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 1.740(2) . ?
O1 C7 1.231(2) . ?
O3 C23 1.271(2) . ?
O2 C16 1.223(2) . ?
N3 C15 1.491(2) . ?
N3 C11 1.494(2) . ?
N3 C10 1.494(2) . ?
N2 C7 1.375(2) . ?
N2 C1 1.389(2) . ?
N2 C8 1.454(2) . ?
N4 C16 1.386(2) . ?
N4 C22 1.389(2) . ?
N4 C13 1.463(2) . ?
N1 C7 1.365(2) . ?
N1 C6 1.387(2) . ?
O4 C23 1.235(3) . ?
N5 C16 1.356(3) . ?
N5 C17 1.372(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.395(3) . ?
C6 C5 1.383(3) . ?
C8 C9 1.519(3) . ?
C17 C18 1.378(3) . ?
C17 C22 1.398(3) . ?
C23 C24 1.505(3) . ?
C22 C21 1.382(3) . ?
C10 C9 1.513(3) . ?
C11 C12 1.514(3) . ?
C5 C4 1.385(3) . ?
C15 C14 1.512(3) . ?
C13 C14 1.506(3) . ?
C13 C12 1.509(3) . ?
C18 C19 1.385(3) . ?
C19 C20 1.377(3) . ?
C2 C3 1.380(3) . ?
C21 C20 1.391(3) . ?
C3 C4 1.381(3) . ?
C24 C24 1.485(4) 2_666 ?
