#------------------------------------------------------------------------------
#$Date: 2024-04-30 00:40:07 +0200 (Tue 30 de Apr de 2024) $
#$Revision: 291409 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/85/7248551.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_7248551
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         '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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    1.00    --  -20.00   0.00 180.00  360
  2  ω   -110.00  70.00   0.50    1.00    --  -20.00   0.00  90.00  360
  3  ω   -110.00   7.00   0.50    1.00    --  -20.00 -70.00 180.00  234
  4  ω   -110.00   7.00   0.50    1.00    --  -20.00 -70.00  90.00  234
  5  ω   -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       'ω 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/[σ²(Fo²)+(0.0761P)²+0.1763P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            d4ce00218k2.cif
_cod_data_source_block           r20230515b_autored
_cod_database_code               7248551
_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   0.983
_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)
;
_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
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 0.64039(14) 0.04332(12) 0.21907(12) 0.0343(3) Uani 1 1 d . . . . .
O2 O 0.81289(12) 0.29432(12) 0.35373(12) 0.0289(2) Uani 1 1 d . . . . .
O3 O 0.39362(12) 0.75530(12) 0.39831(12) 0.0288(2) Uani 1 1 d . . . . .
O4 O 0.65091(11) 0.75470(11) 0.46532(11) 0.0247(2) Uani 1 1 d . . . . .
N3 N 0.16708(14) 0.46898(16) 0.20979(15) 0.0303(3) Uani 1 1 d . . . . .
H3A H 0.073776 0.399913 0.190132 0.036 Uiso 1 1 d R U . . .
H3B H 0.181637 0.559669 0.296036 0.036 Uiso 1 1 d R U . . .
C6 C 0.57188(15) 0.43111(15) 0.33058(14) 0.0183(3) Uani 1 1 d . . . . .
H6 H 0.679524 0.497159 0.391646 0.022 Uiso 1 1 calc R U . . .
C7 C 0.53898(16) 0.26501(15) 0.25637(14) 0.0207(3) Uani 1 1 d . . . . .
C8 C 0.37995(17) 0.16846(16) 0.16467(15) 0.0245(3) Uani 1 1 d . . . . .
H8 H 0.356025 0.054370 0.111653 0.029 Uiso 1 1 calc R U . . .
C9 C 0.25906(17) 0.23658(16) 0.15071(16) 0.0254(3) Uani 1 1 d . . . . .
H9 H 0.152520 0.168812 0.087608 0.031 Uiso 1 1 calc R U . . .
C10 C 0.28949(16) 0.40598(16) 0.22837(15) 0.0219(3) Uani 1 1 d . . . . .
C11 C 0.45134(15) 0.50402(15) 0.31810(14) 0.0189(3) Uani 1 1 d . . . . .
C12 C 0.66544(17) 0.18780(16) 0.27293(15) 0.0230(3) Uani 1 1 d . . . . .
C13 C 0.9428(2) 0.2277(2) 0.3766(2) 0.0398(4) Uani 1 1 d . . . . .
H13A H 0.947104 0.145926 0.275131 0.060 Uiso 1 1 calc R U . . .
H13B H 0.923158 0.178007 0.441171 0.060 Uiso 1 1 calc R U . . .
H13C H 1.046409 0.313891 0.429087 0.060 Uiso 1 1 calc R U . . .
C14 C 0.49162(15) 0.68109(15) 0.39696(14) 0.0199(3) Uani 1 1 d . . . . .
C15 C 0.6988(2) 0.92933(16) 0.54401(18) 0.0327(3) Uani 1 1 d . . . . .
H15A H 0.671007 0.964673 0.467854 0.049 Uiso 1 1 calc R U . . .
H15B H 0.816349 0.972034 0.593587 0.049 Uiso 1 1 calc R U . . .
H15C H 0.641585 0.969412 0.623825 0.049 Uiso 1 1 calc R U . . .
N1 N 0.96423(15) -0.27535(15) 0.24136(15) 0.0336(3) Uani 1 1 d . . . . .
N2 N 0.18924(14) -0.24911(14) -0.00126(15) 0.0288(3) Uani 1 1 d . . . . .
C1 C 0.83123(16) -0.33845(15) 0.17085(15) 0.0226(3) Uani 1 1 d . . . . .
C2 C 0.66268(15) -0.42024(15) 0.08308(14) 0.0187(3) Uani 1 1 d . . . . .
C3 C 0.55577(15) -0.32996(14) 0.08488(14) 0.0191(3) Uani 1 1 d . . . . .
H3 H 0.593513 -0.215445 0.141745 0.023 Uiso 1 1 calc R U . . .
C4 C 0.39278(15) -0.41017(15) 0.00205(14) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.28052(16) -0.31920(15) 0.00201(15) 0.0214(3) 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
C12 O2 C13 115.89(11) . . ?
C14 O4 C15 115.49(11) . . ?
H3A N3 H3B 109.4 . . ?
C10 N3 H3A 109.3 . . ?
C10 N3 H3B 109.4 . . ?
C7 C6 H6 119.1 . . ?
C7 C6 C11 121.79(12) . . ?
C11 C6 H6 119.1 . . ?
C6 C7 C8 118.66(12) . . ?
C6 C7 C12 121.82(12) . . ?
C8 C7 C12 119.52(11) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.85(12) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.33(12) . . ?
C10 C9 H9 119.3 . . ?
N3 C10 C9 119.59(12) . . ?
N3 C10 C11 122.46(12) . . ?
C9 C10 C11 117.89(12) . . ?
C6 C11 C10 119.45(11) . . ?
C6 C11 C14 120.18(11) . . ?
C10 C11 C14 120.37(11) . . ?
O1 C12 O2 122.99(12) . . ?
O1 C12 C7 124.29(13) . . ?
O2 C12 C7 112.71(11) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 O4 122.43(11) . . ?
O3 C14 C11 124.82(12) . . ?
O4 C14 C11 112.73(10) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C1 C2 178.87(15) . . ?
C3 C2 C1 119.45(11) . . ?
C3 C2 C4 120.59(11) . 2_645 ?
C4 C2 C1 119.96(11) 2_645 . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.97(11) . . ?
C4 C3 H3 120.5 . . ?
C2 C4 C5 119.71(11) 2_645 . ?
C3 C4 C2 120.44(11) . 2_645 ?
C3 C4 C5 119.84(11) . . ?
N2 C5 C4 178.54(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 C12 1.2147(16) . ?
O2 C12 1.3381(17) . ?
O2 C13 1.4438(17) . ?
O3 C14 1.2166(15) . ?
O4 C14 1.3382(15) . ?
O4 C15 1.4489(15) . ?
N3 H3A 0.8807 . ?
N3 H3B 0.8806 . ?
N3 C10 1.3551(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3849(17) . ?
C6 C11 1.3941(17) . ?
C7 C8 1.4043(18) . ?
C7 C12 1.4745(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.368(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.4153(19) . ?
C10 C11 1.4223(18) . ?
C11 C14 1.4727(17) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 C1 1.1398(18) . ?
N2 C5 1.1474(18) . ?
C1 C2 1.4426(17) . ?
C2 C3 1.3934(17) . ?
C2 C4 1.4070(17) 2_645 ?
C3 H3 0.9500 . ?
C3 C4 1.3923(17) . ?
C4 C5 1.4385(17) . ?
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
N3 C10 C11 C6 -179.12(12) . . . . ?
N3 C10 C11 C14 0.73(19) . . . . ?
C6 C7 C8 C9 -1.1(2) . . . . ?
C6 C7 C12 O1 174.80(12) . . . . ?
C6 C7 C12 O2 -5.53(18) . . . . ?
C6 C11 C14 O3 -176.67(12) . . . . ?
C6 C11 C14 O4 5.06(17) . . . . ?
C7 C6 C11 C10 0.72(19) . . . . ?
C7 C6 C11 C14 -179.13(11) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C7 C12 O1 -4.4(2) . . . . ?
C8 C7 C12 O2 175.30(11) . . . . ?
C8 C9 C10 N3 179.02(12) . . . . ?
C8 C9 C10 C11 1.8(2) . . . . ?
C9 C10 C11 C6 -2.03(19) . . . . ?
C9 C10 C11 C14 177.81(11) . . . . ?
C10 C11 C14 O3 3.5(2) . . . . ?
C10 C11 C14 O4 -174.79(11) . . . . ?
C11 C6 C7 C8 0.85(19) . . . . ?
C11 C6 C7 C12 -178.33(11) . . . . ?
C12 C7 C8 C9 178.13(12) . . . . ?
C13 O2 C12 O1 -1.1(2) . . . . ?
C13 O2 C12 C7 179.18(12) . . . . ?
C15 O4 C14 O3 1.19(19) . . . . ?
C15 O4 C14 C11 179.51(11) . . . . ?
C1 C2 C3 C4 -178.85(11) . . . . ?
C2 C3 C4 C2 -0.5(2) . . . 2_645 ?
C2 C3 C4 C5 -179.81(11) . . . . ?
C4 C2 C3 C4 0.5(2) 2_645 . . . ?
