A new polymorph of the gastrokinetic drug cisapride monohydrate
Zhou, Xin-Bo; Zhu, Jian-Rong; Gu, Jian-Ming; Hu, Xiu-Rong; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618006836

data_2021127
_publ_section_title
;
 A new polymorph of the gastrokinetic drug cisapride monohydrate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618006836
_journal_volume                  74
_journal_year                    2018
_chemical_formula_moiety         'C23 H29 Cl F N3 O4, H2 O'
_chemical_formula_sum            'C23 H31 Cl F N3 O5'
_chemical_formula_weight         483.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.361(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3225(9)
_cell_length_b                   14.5183(8)
_cell_length_c                   13.8141(8)
_cell_measurement_reflns_used    11147
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.18
_cell_volume                     2445.1(3)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep-3  (Farrugia,2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19055
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.096
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_min         3.178
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9236
_exptl_absorpt_correction_T_min  0.9005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0044(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4348
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0746
_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/[\s^2^(Fo^2^)+(0.0775P)^2^+2.1692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.1981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2638
_reflns_number_total             4348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3687sup3.txt
_cod_data_source_block           cisapride
_cod_database_code               2021127
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.901
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C16-C15 \\sim C16A-C15
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C16) = Uanis(C16A)
Uanis(O4) = Uanis(O4A)
Uanis(C17) = Uanis(C17A)
4. Others
 Sof(H15C)=Sof(H15D)=Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(O4A)=Sof(C16A)=
 Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(O4)=FVAR(1)
5.a Free rotating group:
 O5(H5A,H5B)
5.b Rotating group:
 N1(H1A,H1B)
5.c Ternary CH refined with riding coordinates:
 C9(H9), C13(H13)
5.d Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C15(H15C,
 H15D), C16(H16A,H16B), C17(H17A,H17B), C17A(H17C,H17D), C16A(H16C,H16D)
5.e Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C19(H19), C20(H20), C22(H22), C23(H23), N2(H2)
5.f Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'