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_7248552
_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'
_chemical_formula_sum            'C10 H11 N O4'
_chemical_formula_weight         209.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-02-22 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.473(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0548(5)
_cell_length_b                   7.1932(4)
_cell_length_c                   14.2783(8)
_cell_measurement_reflns_used    5504
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.4410
_cell_measurement_theta_min      2.1400
_cell_volume                     979.48(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.927
_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   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  \w   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0727311000
_diffrn_orient_matrix_UB_12      0.0174976000
_diffrn_orient_matrix_UB_13      0.0220405000
_diffrn_orient_matrix_UB_21      -0.0056975000
_diffrn_orient_matrix_UB_22      -0.0218235000
_diffrn_orient_matrix_UB_23      0.0469873000
_diffrn_orient_matrix_UB_31      0.0146584000
_diffrn_orient_matrix_UB_32      -0.0945619000
_diffrn_orient_matrix_UB_33      -0.0068506000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11837
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.865
_diffrn_reflns_theta_min         3.008
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0768P)^2^+0.3505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1628
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2551
_reflns_number_total             3377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00218k2.cif
_cod_data_source_block           r20211106b
_cod_depositor_comments
'Adding full bibliography for 7248551--7248555.cif.'
_cod_database_code               7248552
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.974
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              77432
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.716