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_7248551
_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         'C10 H11 N O4, C5 H N2'
_chemical_formula_sum            'C15 H12 N3 O4'
_chemical_formula_weight         298.28
_chemical_name_systematic
'Dimethyl 4-aminoisophthalate, 1,2,4,5-tetracyanobenzene'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-17
_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                116.628(2)
_cell_angle_beta                 99.297(2)
_cell_angle_gamma                100.912(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7312(2)
_cell_length_b                   9.7117(2)
_cell_length_c                   9.9811(2)
_cell_measurement_reflns_used    7564
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.3390
_cell_measurement_theta_min      2.4140
_cell_volume                     713.03(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.992
_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   -110.00  70.00   0.50    1.00    --  -20.00   0.00 180.00  360
  2  \w   -110.00  70.00   0.50    1.00    --  -20.00   0.00  90.00  360
  3  \w   -110.00   7.00   0.50    1.00    --  -20.00 -70.00 180.00  234
  4  \w   -110.00   7.00   0.50    1.00    --  -20.00 -70.00  90.00  234
  5  \w   -110.00   3.00   0.50    1.00    --  -20.00 -70.00   0.00  226
;
_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      -0.0190827000
_diffrn_orient_matrix_UB_12      -0.0846272000
_diffrn_orient_matrix_UB_13      -0.0306672000
_diffrn_orient_matrix_UB_21      -0.0830973000
_diffrn_orient_matrix_UB_22      -0.0083269000
_diffrn_orient_matrix_UB_23      -0.0280183000
_diffrn_orient_matrix_UB_31      0.0126896000
_diffrn_orient_matrix_UB_32      -0.0093842000
_diffrn_orient_matrix_UB_33      -0.0716563000
_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  0.0325
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14097
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.378
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             310
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0761P)^2^+0.1763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2986
_reflns_number_total             3510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00218k2.cif
_cod_data_source_block           r20230515b_autored
_cod_depositor_comments
'Adding full bibliography for 7248551--7248555.cif.'
_cod_database_code               7248551
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.974
_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:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C3(H3)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              53313
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.724
_oxdiff_exptl_absorpt_empirical_full_min 0.420