#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:14:52 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281431 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/60/7246097.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_7246097
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_sum            'C24 H28 Cl N5 O5'
_chemical_formula_weight         501.96
_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                103.39(2)
_cell_angle_beta                 108.85(2)
_cell_angle_gamma                106.42(2)
_cell_formula_units_Z            2
_cell_length_a                   10.400(1)
_cell_length_b                   11.282(1)
_cell_length_c                   11.611(1)
_cell_measurement_reflns_used    32435
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.372
_cell_measurement_theta_min      2.246
_cell_volume                     1155.8(4)
_computing_cell_refinement       'APEX3 (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'PHOTON II CPAD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            32435
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.246
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.981
_refine_diff_density_min         -1.032
_refine_diff_density_rms         0.076
_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     316
_refine_ls_number_reflns         4713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0686
_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)+(0.0731P)²+2.6571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3766
_reflns_number_total             4713
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00902a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7246090--7246098.cif.'
_cod_original_cell_volume        1155.7(1)
_cod_database_code               7246097
_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   0.942
_shelx_estimated_absorpt_t_max   0.963
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 0.94032(12) 0.62153(10) 0.42515(9) 0.0521(3) Uani 1 1 d . . . . .
O1 O 0.2170(3) 0.5681(3) -0.0200(2) 0.0404(6) Uani 1 1 d . . . . .
O2 O -0.6919(2) 0.1043(2) 0.15775(19) 0.0236(5) Uani 1 1 d . . . . .
O3 O -0.1490(3) -0.0509(3) 0.2630(2) 0.0443(7) Uani 1 1 d . . . . .
O4 O 0.0660(3) 0.1089(3) 0.3087(2) 0.0485(8) Uani 1 1 d . . . . .
N2 N 0.4672(3) 0.6169(2) 0.0878(2) 0.0232(5) Uani 1 1 d . . . . .
H2A H 0.501949 0.668747 0.051755 0.028 Uiso 1 1 calc R U . . .
N1 N 0.3121(3) 0.4794(3) 0.1338(3) 0.0384(7) Uani 1 1 d . . . . .
N3 N -0.0822(3) 0.2375(3) 0.1439(3) 0.0408(5) Uani 1 1 d . . . . .
H3A H -0.030396 0.193462 0.194273 0.049 Uiso 1 1 calc R U . . .
N4 N -0.4694(3) 0.1249(2) 0.3113(2) 0.0215(5) Uani 1 1 d . . . . .
N5 N -0.6384(3) 0.1534(2) 0.3776(2) 0.0198(5) Uani 1 1 d . . . . .
H5A H -0.717475 0.162829 0.378205 0.024 Uiso 1 1 calc R U . . .
C1 C 0.4535(4) 0.4959(3) 0.2143(3) 0.0311(7) Uani 1 1 d . . . . .
C2 C 0.5051(5) 0.4481(3) 0.3110(3) 0.0429(10) Uani 1 1 d . . . . .
H2 H 0.440418 0.390739 0.332103 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6561(5) 0.4881(3) 0.3760(3) 0.0455(10) Uani 1 1 d . . . . .
H3 H 0.694186 0.457451 0.441870 0.055 Uiso 1 1 calc R U . . .
C4 C 0.7510(4) 0.5737(3) 0.3432(3) 0.0345(8) Uani 1 1 d . . . . .
C5 C 0.7018(3) 0.6241(3) 0.2465(3) 0.0263(6) Uani 1 1 d . . . . .
H5 H 0.766520 0.681718 0.225637 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5515(3) 0.5836(3) 0.1838(3) 0.0234(6) Uani 1 1 d . . . . .
C7 C 0.3214(3) 0.5563(3) 0.0581(3) 0.0294(7) Uani 1 1 d . . . . .
C8A C 0.1564(5) 0.4139(5) 0.1199(5) 0.0211(9) Uani 0.619(6) 1 d . . P . .
H8A H 0.097775 0.453632 0.069537 0.025 Uiso 1 1 calc R U . . .
C8B C 0.2031(9) 0.3757(8) 0.1506(8) 0.0211(9) Uani 0.381(6) 1 d . . P . .
C9 C 0.0939(4) 0.2718(4) 0.0395(4) 0.0408(5) Uani 1 1 d . . . . .
H9A H 0.085770 0.263671 -0.047827 0.049 Uiso 1 1 calc R U . . .
H9B H 0.161994 0.232722 0.075317 0.049 Uiso 1 1 calc R U . . .
C10 C -0.0515(4) 0.1962(4) 0.0311(4) 0.0408(5) Uani 1 1 d . . . . .
H10A H -0.125988 0.199502 -0.042917 0.049 Uiso 1 1 calc R U . . .
H10B H -0.062970 0.104531 0.012706 0.049 Uiso 1 1 calc R U . . .
C11 C -0.0005(4) 0.3674(4) 0.2374(4) 0.0481(11) Uani 1 1 d . . . . .
H11A H 0.014494 0.361931 0.322563 0.058 Uiso 1 1 calc R U . . .
H11B H -0.061251 0.418241 0.221386 0.058 Uiso 1 1 calc R U . . .
C12 C 0.1451(4) 0.4434(3) 0.2438(3) 0.0303(7) Uani 1 1 d . . . . .
H12A H 0.165881 0.537014 0.278286 0.036 Uiso 1 1 calc R U . . .
H12B H 0.220077 0.425778 0.304349 0.036 Uiso 1 1 calc R U . . .
C13 C -0.2278(3) 0.1621(3) 0.1291(3) 0.0272(7) Uani 1 1 d . . . . .
H13A H -0.238642 0.070554 0.110514 0.033 Uiso 1 1 calc R U . . .
H13B H -0.298309 0.165747 0.052617 0.033 Uiso 1 1 calc R U . . .
C14 C -0.2715(4) 0.1993(3) 0.2379(4) 0.0357(8) Uani 1 1 d . . . . .
H14A H -0.294265 0.277115 0.239501 0.043 Uiso 1 1 calc R U . . .
H14B H -0.189809 0.220892 0.320016 0.043 Uiso 1 1 calc R U . . .
C15 C -0.4041(3) 0.0877(3) 0.2228(3) 0.0236(6) Uani 1 1 d . . . . .
H15A H -0.478171 0.054953 0.134025 0.028 Uiso 1 1 calc R U . . .
H15B H -0.375164 0.015925 0.236948 0.028 Uiso 1 1 calc R U . . .
C16 C -0.6092(3) 0.1251(3) 0.2707(3) 0.0196(6) Uani 1 1 d . . . . .
C17 C -0.5207(3) 0.1648(3) 0.4860(3) 0.0199(6) Uani 1 1 d . . . . .
C18 C -0.5003(3) 0.1845(3) 0.6138(3) 0.0236(6) Uani 1 1 d . . . . .
H18 H -0.571780 0.195265 0.642018 0.028 Uiso 1 1 calc R U . . .
C19 C -0.3680(4) 0.1877(3) 0.6987(3) 0.0274(7) Uani 1 1 d . . . . .
H19 H -0.351183 0.200746 0.785191 0.033 Uiso 1 1 calc R U . . .
C20 C -0.2609(3) 0.1717(3) 0.6572(3) 0.0282(7) Uani 1 1 d . . . . .
H20 H -0.173683 0.174883 0.716438 0.034 Uiso 1 1 calc R U . . .
C21 C -0.2819(3) 0.1511(3) 0.5283(3) 0.0263(6) Uani 1 1 d . . . . .
H21 H -0.210774 0.139844 0.499810 0.032 Uiso 1 1 calc R U . . .
C22 C -0.4127(3) 0.1480(3) 0.4448(3) 0.0205(6) Uani 1 1 d . . . . .
C23 C -0.0199(3) 0.0277(4) 0.3373(3) 0.0301(7) Uani 1 1 d . . . . .
C24 C 0.0387(3) 0.0347(3) 0.4759(3) 0.0225(6) Uani 1 1 d . . . . .
H24 H 0.135682 0.091760 0.530803 0.027 Uiso 1 1 calc R U . . .
O5W O -0.3798(3) -0.1846(2) 0.0286(2) 0.0293(5) Uani 1 1 d . . . . .
H5WB H -0.363(5) -0.170(5) -0.039(5) 0.066(15) Uiso 1 1 d . . . . .
H5WA H -0.292(5) -0.139(4) 0.098(4) 0.041(11) 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'
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'
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
C7 N2 C6 110.6(3) . . ?
C7 N1 C1 109.6(3) . . ?
C7 N1 C8B 141.4(4) . . ?
C1 N1 C8B 108.7(4) . . ?
C7 N1 C8A 112.9(3) . . ?
C1 N1 C8A 137.0(3) . . ?
C8B N1 C8A 30.7(3) . . ?
C11 N3 C13 120.5(3) . . ?
C11 N3 C10 120.4(3) . . ?
C13 N3 C10 115.0(3) . . ?
C16 N4 C22 109.2(2) . . ?
C16 N4 C15 123.4(2) . . ?
C22 N4 C15 126.8(2) . . ?
C16 N5 C17 109.6(2) . . ?
C2 C1 N1 132.8(3) . . ?
C2 C1 C6 120.8(3) . . ?
N1 C1 C6 106.3(3) . . ?
C1 C2 C3 118.0(3) . . ?
C2 C3 C4 120.2(3) . . ?
C3 C4 C5 122.9(3) . . ?
C3 C4 Cl1 119.5(3) . . ?
C5 C4 Cl1 117.6(3) . . ?
C6 C5 C4 115.8(3) . . ?
C5 C6 N2 130.8(3) . . ?
C5 C6 C1 122.3(3) . . ?
N2 C6 C1 106.9(3) . . ?
O1 C7 N2 127.3(3) . . ?
O1 C7 N1 126.1(3) . . ?
N2 C7 N1 106.6(3) . . ?
C12 C8A C9 115.4(4) . . ?
C12 C8A N1 112.6(3) . . ?
C9 C8A N1 110.3(4) . . ?
C10 C9 C8A 114.5(3) . . ?
N3 C10 C9 117.3(3) . . ?
N3 C11 C12 118.4(3) . . ?
C8A C12 C11 114.5(3) . . ?
N3 C13 C14 119.1(3) . . ?
C13 C14 C15 110.9(3) . . ?
N4 C15 C14 113.8(2) . . ?
O2 C16 N5 126.6(3) . . ?
O2 C16 N4 126.0(3) . . ?
N5 C16 N4 107.4(2) . . ?
C18 C17 N5 132.0(3) . . ?
C18 C17 C22 120.8(3) . . ?
N5 C17 C22 107.2(2) . . ?
C17 C18 C19 117.3(3) . . ?
C20 C19 C18 121.6(3) . . ?
C19 C20 C21 121.1(3) . . ?
C22 C21 C20 117.1(3) . . ?
C21 C22 N4 131.3(3) . . ?
C21 C22 C17 122.1(3) . . ?
N4 C22 C17 106.6(2) . . ?
O3 C23 O4 126.1(3) . . ?
O3 C23 C24 118.0(3) . . ?
O4 C23 C24 115.8(3) . . ?
C24 C24 C23 123.8(3) 2_556 . ?
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 C4 1.739(4) . ?
O1 C7 1.233(4) . ?
O2 C16 1.237(3) . ?
O3 C23 1.248(4) . ?
O4 C23 1.271(4) . ?
N2 C7 1.361(4) . ?
N2 C6 1.379(4) . ?
N1 C7 1.378(4) . ?
N1 C1 1.395(5) . ?
N1 C8B 1.480(8) . ?
N1 C8A 1.514(5) . ?
N3 C11 1.418(4) . ?
N3 C13 1.442(4) . ?
N3 C10 1.452(4) . ?
N4 C16 1.377(4) . ?
N4 C22 1.397(4) . ?
N4 C15 1.451(4) . ?
N5 C16 1.361(4) . ?
N5 C17 1.393(4) . ?
C1 C2 1.377(5) . ?
C1 C6 1.403(4) . ?
C2 C3 1.384(6) . ?
C3 C4 1.388(6) . ?
C4 C5 1.392(4) . ?
C5 C6 1.374(4) . ?
C8A C12 1.451(6) . ?
C8A C9 1.479(6) . ?
C9 C10 1.469(4) . ?
C11 C12 1.482(5) . ?
C13 C14 1.488(4) . ?
C14 C15 1.509(4) . ?
C17 C18 1.383(4) . ?
C17 C22 1.397(4) . ?
C18 C19 1.394(4) . ?
C19 C20 1.387(5) . ?
C20 C21 1.393(4) . ?
C21 C22 1.377(4) . ?
C23 C24 1.499(4) . ?
C24 C24 1.309(6) 2_556 ?
