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_7248553
_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_absolute_configuration ad
_chemical_formula_moiety         'C10 H11 N O4, C10 H2 N4'
_chemical_formula_sum            'C20 H13 N5 O4'
_chemical_formula_weight         387.35
_chemical_name_systematic
'Dimethyl aminoterephthalate, 1,2,4,5-tetracyanobenzene'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-08-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-16 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                95.079(2)
_cell_angle_beta                 90.432(2)
_cell_angle_gamma                97.825(2)
_cell_formula_units_Z            1
_cell_length_a                   6.5102(2)
_cell_length_b                   7.1433(2)
_cell_length_c                   9.9181(2)
_cell_measurement_reflns_used    6649
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      30.6460
_cell_measurement_theta_min      2.0720
_cell_volume                     455.06(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.857
_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    -21.00  36.00   0.50    1.20    --    5.19 -92.00  62.00  114
  2  \w    -21.00  66.00   0.50    1.20    --   -6.68  38.00-140.53  174
  3  \w     14.00  62.00   0.50    1.20    --   -6.68  77.00-120.00   96
  4  \w    -30.00   4.00   0.50    1.20    --   -6.68  77.00-120.00   68
  5  \w    -21.00  65.00   0.50    1.20    --   -6.68  37.00   0.00  172
  6  \w    -21.00  64.00   0.50    1.20    --   -6.68  37.00  60.00  170
  7  \w      8.00  40.00   0.50    1.20    --    5.19  92.00 175.00   64
  8  \w    -21.00  37.00   0.50    1.20    --   -6.68  37.00 120.00  116
  9  \w    -22.00  67.00   0.50    1.20    --   -6.68  19.00-180.00  178
 10  \w    -19.00  17.00   0.50    1.20    --   -6.68 -77.00-150.00   72
 11  \w    -53.00 -27.00   0.50    1.20    --   -6.68 -77.00-150.00   52
 12  \w    -21.00  26.00   0.50    1.20    --   -6.68 -99.00 -90.00   94
 13  \w    -36.00  20.00   0.50    1.20    --   -6.68 -92.00  62.00  112
 14  \w    -36.00 -10.00   0.50    1.20    --   -6.68  92.00 175.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0463066000
_diffrn_orient_matrix_UB_12      0.0762434000
_diffrn_orient_matrix_UB_13      0.0318752000
_diffrn_orient_matrix_UB_21      -0.0653805000
_diffrn_orient_matrix_UB_22      -0.0015494000
_diffrn_orient_matrix_UB_23      -0.0577342000
_diffrn_orient_matrix_UB_31      -0.0753684000
_diffrn_orient_matrix_UB_32      -0.0656743000
_diffrn_orient_matrix_UB_33      0.0284187000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12154
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.771
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.785
_diffrn_reflns_theta_min         2.062
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       plate
_exptl_crystal_F_000             200
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1540 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4393
_refine_ls_number_restraints     219
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0445P)^2^+0.0977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.685
_reflns_number_gt                3797
_reflns_number_total             4393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00218k2.cif
_cod_data_source_block           zxk-2ad-tcnb-h-120k_auto
_cod_depositor_comments
'Adding full bibliography for 7248551--7248555.cif.'
_cod_database_code               7248553
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.980
_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. Uiso/Uaniso restraints and constraints
Uanis(N4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H1)=Sof(N4)=Sof(H4A)=Sof(H4B)=1-FVAR(1)
 Sof(H6)=Sof(N3)=Sof(H3A)=Sof(H3B)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C15(H15), C6(H6), C14(H14), C4(H4)
5.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
5.c Idealised Me refined as rotating group:
 C(HA,HB,HC), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              76506
_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 1.229
_oxdiff_exptl_absorpt_empirical_full_min 0.849