Mechanochemical synthesis and 35Cl NMR crystallography of ionic cocrystals of phenothiazine drugs
Dowdell, Zachary T.; Peach, Austin A.; Purdie, John P.; Holmes, Sean T.; Watanabe, Lara K.; Rawson, Jeremy M.; Schurko, Robert W.; CrystEngComm 27 (2025) 3752–3768; doi:10.1039/D5CE00426H

data_7250347
_publ_section_title
;
 Mechanochemical synthesis and 35Cl NMR crystallography of ionic
 cocrystals of phenothiazine drugs
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3752
_journal_page_last               3768
_journal_paper_doi               10.1039/D5CE00426H
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'Cl, C17 H20 Cl N2 S, C2 H2 O2'
_chemical_formula_sum            'C19 H22 Cl2 N2 O2 S'
_chemical_formula_weight         413.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_audit_creation_date             2025-01-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-19 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.9090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.9241(10)
_cell_length_b                   7.5422(3)
_cell_length_c                   21.1043(8)
_cell_measurement_reflns_used    9854
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      25.408
_cell_measurement_theta_min      2.911
_cell_volume                     4100.3(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36003
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.426
_diffrn_reflns_theta_min         2.903
_exptl_absorpt_coefficient_mu    0.434
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0604 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.9526.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00262(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0303
_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/[\s^2^(Fo^2^)+(0.0248P)^2^+5.1122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3196
_reflns_number_total             3774
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00426h2.cif
_cod_data_source_block           lw_jp_cpz_fum_2_1_2ndxxtal_c2c_a
_cod_depositor_comments
'Adding full bibliography for 7250347--7250348.cif.'
_cod_database_code               7250347
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C11(H11), C9(H9), C8(H8), C3(H3), C5(H5), C4(H4), C19(H19)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              35076
_olex2_submission_special_instructions 'No special instructions were received'