How does the combination of the nitro group and fluorine atoms affect the (co)crystallization behaviour of arylenediamines?
Vaganova, Tamara A.; Gatilov, Yurij V.; Kryuchkova, Natalia A.; Pishchur, Denis P.; Zhukovets, Anastasia A.; Malykhin, Evgenij V.; CrystEngComm 25 (2023) 3284–3298; doi:10.1039/D3CE00327B

data_7246691
_publ_section_title
;
 How does the combination of the nitro group and fluorine atoms affect the
 (co)crystallization behaviour of arylenediamines?
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3284
_journal_page_last               3298
_journal_paper_doi               10.1039/D3CE00327B
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C6 H7 N3 O2, C12 H24 O6'
_chemical_formula_sum            'C18 H31 N3 O8'
_chemical_formula_weight         417.46
_chemical_melting_point          400.6
_chemical_name_systematic
;
2,4-diaminenitrobenzene 18-crown-6 1:1 cocrystal
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.477(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7751(10)
_cell_length_b                   11.1808(6)
_cell_length_c                   14.7876(11)
_cell_measurement_reflns_used    3313
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.40
_cell_volume                     2147.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.968
_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  0.0468
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5827
_diffrn_reflns_point_group_measured_fraction_full 0.732
_diffrn_reflns_point_group_measured_fraction_max 0.685
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.404
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.8435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 889 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0637P)^2^+0.3242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.413
_reflns_Friedel_fraction_full    0.479
_reflns_Friedel_fraction_max     0.400
_reflns_number_gt                3035
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00327b2.cif
_cod_data_source_block           Dcr_mal169_1
_cod_depositor_comments
'Adding full bibliography for 7246683--7246691.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7246691
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              28227
_shelx_hkl_checksum              1948