Modulation of luminescence properties of cocrystals composed of amino substituted dimethyl phthalates and 1,2,4,5-tetracyanobenzene by crystal engineering
Zhang, Xiaokai; Li, Zhonghua; Han, Rui; Lin, Jiawei; Li, Maolin; Zhou, Jianmin; Wu, Songgu; Gong, Junbo; CrystEngComm 26 (2024) 2976–2988; doi:10.1039/D4CE00218K

data_7248555
_publ_section_title
;
 Modulation of luminescence properties of cocrystals composed of amino
 substituted dimethyl phthalates and 1,2,4,5-tetracyanobenzene by crystal
 engineering
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              2976
_journal_page_last               2988
_journal_paper_doi               10.1039/D4CE00218K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '2(C10 H11 N O4), C10 H2 N4'
_chemical_formula_sum            'C30 H24 N6 O8'
_chemical_formula_weight         596.55
_chemical_name_systematic
'dimethyl 5-aminoisophthalate, 1,2,4,5-tetracyanobenzene'
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-16 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.461(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6502(3)
_cell_length_b                   22.7523(7)
_cell_length_c                   18.2160(5)
_cell_measurement_reflns_used    11656
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      35.5930
_cell_measurement_theta_min      2.1080
_cell_volume                     3107.45(18)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -120.00  60.00   0.50    8.00    --  -30.00   0.00 180.00  360
  2  \w   -120.00  60.00   0.50    8.00    --  -30.00   0.00   0.00  360
  3  \w    -66.00  60.00   0.50    8.00    --  -30.00  70.00 180.00  252
  4  \w   -120.00   6.00   0.50    8.00    --  -30.00 -70.00 180.00  252
  5  \w    -66.00  54.00   0.50    8.00    --  -30.00  70.00   0.00  240
  6  \w    -66.00  52.00   0.50    8.00    --  -30.00  70.00  90.00  236
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn 944+'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0354817000
_diffrn_orient_matrix_UB_12      -0.0033278000
_diffrn_orient_matrix_UB_13      -0.0388156000
_diffrn_orient_matrix_UB_21      -0.0297112000
_diffrn_orient_matrix_UB_22      -0.0286662000
_diffrn_orient_matrix_UB_23      0.0066755000
_diffrn_orient_matrix_UB_31      -0.0825012000
_diffrn_orient_matrix_UB_32      0.0117837000
_diffrn_orient_matrix_UB_33      0.0052547000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            49760
_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         2.282
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0891
_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^)+(0.1431P)^2^+1.6733P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2337
_refine_ls_wR_factor_ref         0.2585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4272
_reflns_number_total             6360
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00218k2.cif
_cod_data_source_block           r20230610b_autored
_cod_depositor_comments
'Adding full bibliography for 7248551--7248555.cif.'
_cod_database_code               7248555
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N1(H1A,H1B), N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C11(H11), C13(H13), C15(H15), C23(H23), C26(H26)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              23352
_shelx_fab_checksum              68819
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.291
_oxdiff_exptl_absorpt_empirical_full_min 0.452