Evaluation of synthon influence on ethenzamide–polyphenol pharmaceutical cocrystals
Acebedo-Martínez, Francisco Javier; Domínguez-Martín, Alicia; Alarcón-Payer, Carolina; Frontera, Antonio; Ibáñez, Ángel; Choquesillo-Lazarte, Duane; CrystEngComm 25 (2023) 3150–3163; doi:10.1039/D3CE00234A

data_7246712
_publ_section_title
;
 Evaluation of synthon influence on ethenzamide--polyphenol pharmaceutical
 cocrystals
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              3150
_journal_page_last               3163
_journal_paper_doi               10.1039/D3CE00234A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         '2(C9 H11 N O2), C6 H6 O3'
_chemical_formula_sum            'C24 H28 N2 O7'
_chemical_formula_weight         456.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-03-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
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2023-03-11 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.780(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9310(7)
_cell_length_b                   10.0681(6)
_cell_length_c                   12.1027(8)
_cell_measurement_reflns_used    574
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      65.77
_cell_measurement_theta_min      27.25
_cell_volume                     1192.52(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker Apex 4, 2022'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16420
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        66.498
_diffrn_reflns_theta_max         66.498
_diffrn_reflns_theta_min         4.391
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0880 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.8464.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.16(13)
_refine_ls_extinction_coef       0.0096(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3793
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0635P)^2^+0.0422P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.820
_reflns_number_gt                3301
_reflns_number_total             3793
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00234a2.cif
_cod_data_source_block           ephl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7246710--7246713.cif.
;
_cod_database_code               7246712
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C21(H21), C23(H23), C25(H25)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O6(H6A), O7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'