#------------------------------------------------------------------------------
#$Date: 2024-04-30 00:40:07 +0200 (Tue 30 de Apr de 2024) $
#$Revision: 291409 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/85/7248554.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7248554
loop_
_publ_author_name
'Zhang, Xiaokai'
'Li, Zhonghua'
'Han, Rui'
'Lin, Jiawei'
'Li, Maolin'
'Zhou, Jianmin'
'Wu, Songgu'
'Gong, Junbo'
_publ_section_title
;
 Modulation of Luminescent Properties of Cocrystals Composed of Amino
 Substituted Dimethyl Phthalates and 1,2,4,5-Tetracyanobenzene by Crystal
 Engineering
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D4CE00218K
_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 aminoterephthalate,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             2023-06-10
_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                100.928(2)
_cell_angle_beta                 98.038(2)
_cell_angle_gamma                106.164(2)
_cell_formula_units_Z            1
_cell_length_a                   6.7011(2)
_cell_length_b                   9.6663(2)
_cell_length_c                   11.8016(3)
_cell_measurement_reflns_used    8149
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.2080
_cell_measurement_theta_min      2.2440
_cell_volume                     705.72(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 0.898
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    2.00    --  -20.00   0.00   0.00  360
  2  ω   -110.00  55.00   0.50    2.00    --  -20.00   0.00  90.00  330
  3  ω   -110.00   7.00   0.50    2.00    --  -20.00 -70.00   0.00  234
  4  ω   -110.00   7.00   0.50    2.00    --  -20.00 -70.00 180.00  234
  5  ω   -110.00  -1.00   0.50    2.00    --  -20.00 -70.00  90.00  218
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn 944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0840791000
_diffrn_orient_matrix_UB_12      0.0679683000
_diffrn_orient_matrix_UB_13      0.0204599000
_diffrn_orient_matrix_UB_21      -0.0171048000
_diffrn_orient_matrix_UB_22      0.0148406000
_diffrn_orient_matrix_UB_23      -0.0565453000
_diffrn_orient_matrix_UB_31      -0.0728836000
_diffrn_orient_matrix_UB_32      0.0368015000
_diffrn_orient_matrix_UB_33      0.0171457000
_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  0.0356
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18343
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.763
_diffrn_reflns_theta_min         1.795
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74560
_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_colour_primary    brown
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             310
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         5494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0591
_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/[σ²(Fo²)+(0.0869P)²+0.1626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1741
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4059
_reflns_number_total             5494
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00218k2.cif
_cod_data_source_block           r20230608c_autored
_cod_database_code               7248554
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.973
_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), C7(H7), C8(H8), C13(H13)
2.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C10(H10A,H10B,H10C)
;
_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 2.186
_oxdiff_exptl_absorpt_empirical_full_min 0.597
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.10920(17) 0.64374(12) 0.65207(8) 0.0355(2) Uani 1 1 d . . . . .
O2 O -0.14487(15) 0.63184(11) 0.83697(8) 0.0293(2) Uani 1 1 d . . . . .
O3 O 0.58883(16) 0.21381(11) 0.70391(9) 0.0333(2) Uani 1 1 d . . . . .
O4 O 0.57510(15) 0.25868(10) 0.89525(8) 0.0290(2) Uani 1 1 d . . . . .
N1 N 0.3801(2) 0.34403(15) 0.56551(10) 0.0349(3) Uani 1 1 d . . . . .
H1A H 0.399081 0.257275 0.564271 0.042 Uiso 1 1 d R U . . .
H1B H 0.286627 0.336417 0.502399 0.042 Uiso 1 1 d R U . . .
C1 C -0.2874(2) 0.72044(15) 0.83502(12) 0.0296(3) Uani 1 1 d . . . . .
H1C H -0.314681 0.739574 0.756603 0.044 Uiso 1 1 calc R U . . .
H1D H -0.222311 0.814930 0.893928 0.044 Uiso 1 1 calc R U . . .
H1E H -0.421573 0.666704 0.853211 0.044 Uiso 1 1 calc R U . . .
C2 C -0.06661(18) 0.60262(13) 0.74055(10) 0.0237(2) Uani 1 1 d . . . . .
C3 C 0.08407(18) 0.51533(12) 0.75442(10) 0.0219(2) Uani 1 1 d . . . . .
C4 C 0.16248(19) 0.46853(13) 0.65771(10) 0.0235(2) Uani 1 1 d . . . . .
H4 H 0.118191 0.491371 0.585388 0.028 Uiso 1 1 calc R U . . .
C5 C 0.30780(19) 0.38703(13) 0.66352(10) 0.0229(2) Uani 1 1 d . . . . .
C6 C 0.37107(18) 0.35564(12) 0.77305(10) 0.0214(2) Uani 1 1 d . . . . .
C7 C 0.28830(19) 0.40490(14) 0.87010(10) 0.0247(2) Uani 1 1 d . . . . .
H7 H 0.331352 0.383307 0.943165 0.030 Uiso 1 1 calc R U . . .
C8 C 0.14613(19) 0.48384(14) 0.86270(10) 0.0250(2) Uani 1 1 d . . . . .
H8 H 0.091521 0.516131 0.929428 0.030 Uiso 1 1 calc R U . . .
C9 C 0.52164(18) 0.27070(13) 0.78499(10) 0.0239(2) Uani 1 1 d . . . . .
C10 C 0.7040(2) 0.16347(16) 0.91078(14) 0.0364(3) Uani 1 1 d . . . . .
H10A H 0.633044 0.064852 0.858243 0.055 Uiso 1 1 calc R U . . .
H10B H 0.723904 0.155070 0.992776 0.055 Uiso 1 1 calc R U . . .
H10C H 0.842530 0.205936 0.891865 0.055 Uiso 1 1 calc R U . . .
N2 N 0.5645(2) 0.17517(16) 0.38535(12) 0.0401(3) Uani 1 1 d . . . . .
N3 N 1.1380(2) -0.00093(14) 0.83843(11) 0.0359(3) Uani 1 1 d . . . . .
C11 C 0.6930(2) 0.12775(15) 0.42007(11) 0.0291(3) Uani 1 1 d . . . . .
C12 C 0.85068(18) 0.06403(13) 0.46186(11) 0.0238(2) Uani 1 1 d . . . . .
C13 C 0.89464(19) 0.06365(13) 0.58043(11) 0.0244(2) Uani 1 1 d . . . . .
H13 H 0.823692 0.106903 0.634509 0.029 Uiso 1 1 calc R U . . .
C14 C 1.04452(18) -0.00128(12) 0.61839(10) 0.0228(2) Uani 1 1 d . . . . .
C15 C 1.09515(19) -0.00172(13) 0.74109(11) 0.0261(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C1 117.20(9) . . ?
C9 O4 C10 115.76(10) . . ?
H1A N1 H1B 109.4 . . ?
C5 N1 H1A 109.2 . . ?
C5 N1 H1B 109.6 . . ?
O2 C1 H1C 109.5 . . ?
O2 C1 H1D 109.5 . . ?
O2 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
O1 C2 O2 124.16(11) . . ?
O1 C2 C3 123.44(11) . . ?
O2 C2 C3 112.38(9) . . ?
C4 C3 C2 117.73(10) . . ?
C4 C3 C8 120.87(10) . . ?
C8 C3 C2 121.39(11) . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.42(10) . . ?
C5 C4 H4 119.3 . . ?
N1 C5 C4 118.85(10) . . ?
N1 C5 C6 123.44(11) . . ?
C4 C5 C6 117.70(10) . . ?
C5 C6 C9 120.44(11) . . ?
C7 C6 C5 119.53(10) . . ?
C7 C6 C9 120.02(10) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 121.96(10) . . ?
C8 C7 H7 119.0 . . ?
C3 C8 H8 120.7 . . ?
C7 C8 C3 118.50(11) . . ?
C7 C8 H8 120.7 . . ?
O3 C9 O4 122.36(11) . . ?
O3 C9 C6 124.64(11) . . ?
O4 C9 C6 112.99(10) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 178.38(16) . . ?
C13 C12 C11 119.73(11) . . ?
C13 C12 C14 121.02(10) . 2_756 ?
C14 C12 C11 119.25(11) 2_756 . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.73(11) . . ?
C14 C13 H13 120.6 . . ?
C12 C14 C15 119.80(10) 2_756 . ?
C13 C14 C12 120.25(11) . 2_756 ?
C13 C14 C15 119.94(11) . . ?
N3 C15 C14 179.10(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2112(14) . ?
O2 C1 1.4503(14) . ?
O2 C2 1.3331(15) . ?
O3 C9 1.2164(16) . ?
O4 C9 1.3361(14) . ?
O4 C10 1.4454(15) . ?
N1 H1A 0.8804 . ?
N1 H1B 0.8805 . ?
N1 C5 1.3534(16) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C2 C3 1.4962(16) . ?
C3 C4 1.3739(16) . ?
C3 C8 1.4028(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.4150(16) . ?
C5 C6 1.4177(15) . ?
C6 C7 1.4015(17) . ?
C6 C9 1.4756(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.3799(17) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N2 C11 1.1452(17) . ?
N3 C15 1.1425(17) . ?
C11 C12 1.4391(16) . ?
C12 C13 1.3901(16) . ?
C12 C14 1.4012(17) 2_756 ?
C13 H13 0.9500 . ?
C13 C14 1.3911(15) . ?
C14 C15 1.4414(16) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -6.05(18) . . . . ?
O1 C2 C3 C8 173.04(12) . . . . ?
O2 C2 C3 C4 175.06(10) . . . . ?
O2 C2 C3 C8 -5.85(16) . . . . ?
N1 C5 C6 C7 179.85(12) . . . . ?
N1 C5 C6 C9 -0.64(18) . . . . ?
C1 O2 C2 O1 -0.94(18) . . . . ?
C1 O2 C2 C3 177.94(10) . . . . ?
C2 C3 C4 C5 179.20(10) . . . . ?
C2 C3 C8 C7 -178.94(11) . . . . ?
C3 C4 C5 N1 -179.88(11) . . . . ?
C3 C4 C5 C6 -0.30(17) . . . . ?
C4 C3 C8 C7 0.12(18) . . . . ?
C4 C5 C6 C7 0.29(17) . . . . ?
C4 C5 C6 C9 179.80(10) . . . . ?
C5 C6 C7 C8 -0.08(18) . . . . ?
C5 C6 C9 O3 -5.45(18) . . . . ?
C5 C6 C9 O4 176.05(10) . . . . ?
C6 C7 C8 C3 -0.13(19) . . . . ?
C7 C6 C9 O3 174.06(12) . . . . ?
C7 C6 C9 O4 -4.45(16) . . . . ?
C8 C3 C4 C5 0.10(18) . . . . ?
C9 C6 C7 C8 -179.59(11) . . . . ?
C10 O4 C9 O3 -4.94(17) . . . . ?
C10 O4 C9 C6 173.60(10) . . . . ?
C11 C12 C13 C14 178.69(11) . . . . ?
C12 C13 C14 C12 0.38(18) . . . 2_756 ?
C12 C13 C14 C15 179.26(11) . . . . ?
C14 C12 C13 C14 -0.39(18) 2_756 . . . ?
