# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r20230515b_autored
_database_code_depnum_ccdc_archive 'CCDC 2314832'
loop_
_audit_author_name
_audit_author_address
'Xiaokai Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2023-12-16 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2023-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'Dimethyl 4-aminoisophthalate, 1,2,4,5-tetracyanobenzene'
_chemical_formula_moiety         'C10 H11 N O4, C5 H N2'
_chemical_formula_sum            'C15 H12 N3 O4'
_chemical_formula_weight         298.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7312(2)
_cell_length_b                   9.7117(2)
_cell_length_c                   9.9811(2)
_cell_angle_alpha                116.628(2)
_cell_angle_beta                 99.297(2)
_cell_angle_gamma                100.912(2)
_cell_volume                     713.03(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7564
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.3390
_cell_measurement_theta_min      2.4140
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.974
_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_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             310
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2986
_reflns_number_total             3510
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.075
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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 . . . ?

_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
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r20211106b
_database_code_depnum_ccdc_archive 'CCDC 2334584'
loop_
_audit_author_name
_audit_author_address
'xiaokai zhang'
;Tianjin University
China
;
_audit_update_record             
;
2024-02-22 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2021-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N O4'
_chemical_formula_sum            'C10 H11 N O4'
_chemical_formula_weight         209.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0548(5)
_cell_length_b                   7.1932(4)
_cell_length_c                   14.2783(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.473(5)
_cell_angle_gamma                90
_cell_volume                     979.48(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5504
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.4410
_cell_measurement_theta_min      2.1400
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.974
_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_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  ω   -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       'ω 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_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2551
_reflns_number_total             3377
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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+0.001xFc²λ³/sin(2θ)]^-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_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      1.041
_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/[σ²(Fo²)+(0.0768P)²+0.3505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1628
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.71215(10) 0.17780(16) 0.50164(7) 0.0256(2) Uani 1 1 d . . . . .
O2 O 0.78803(11) 0.06581(17) 0.65613(8) 0.0302(3) Uani 1 1 d . . . . .
O3 O 0.24840(10) 0.39813(16) 0.35699(7) 0.0247(2) Uani 1 1 d . . . . .
O4 O 0.09396(11) 0.43026(19) 0.43938(8) 0.0336(3) Uani 1 1 d . . . . .
N1 N 0.19740(13) 0.42223(19) 0.63922(9) 0.0270(3) Uani 1 1 d . . . . .
H1A H 0.125921 0.402725 0.587828 0.032 Uiso 1 1 d GR . . . .
H1B H 0.184872 0.367216 0.689323 0.032 Uiso 1 1 d GR . . . .
C1 C 0.84310(16) 0.1185(2) 0.48957(13) 0.0299(3) Uani 1 1 d . . . . .
H1C H 0.846672 0.158384 0.424788 0.045 Uiso 1 1 calc GR . . . .
H1D H 0.849975 -0.017299 0.494257 0.045 Uiso 1 1 calc GR . . . .
H1E H 0.921431 0.174176 0.541498 0.045 Uiso 1 1 calc GR . . . .
C2 C 0.69781(13) 0.1437(2) 0.59036(10) 0.0211(3) Uani 1 1 d . . . . .
C3 C 0.56445(13) 0.2150(2) 0.59897(10) 0.0197(3) Uani 1 1 d . . . . .
C4 C 0.54938(14) 0.2289(2) 0.69316(10) 0.0233(3) Uani 1 1 d . . . . .
H4 H 0.623962 0.190693 0.749482 0.028 Uiso 1 1 calc R . . . .
C5 C 0.42839(14) 0.2970(2) 0.70475(10) 0.0234(3) Uani 1 1 d . . . . .
H5 H 0.421100 0.306454 0.769311 0.028 Uiso 1 1 calc R . . . .
C6 C 0.31392(13) 0.3535(2) 0.62294(10) 0.0200(3) Uani 1 1 d . . . . .
C7 C 0.32854(13) 0.33787(19) 0.52746(9) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.45419(13) 0.27172(19) 0.51758(10) 0.0190(3) Uani 1 1 d . . . . .
H8 H 0.464382 0.265420 0.453749 0.023 Uiso 1 1 calc R . . . .
C9 C 0.21216(13) 0.3925(2) 0.43957(10) 0.0209(3) Uani 1 1 d . . . . .
C10 C 0.13811(17) 0.4534(3) 0.26907(11) 0.0316(4) Uani 1 1 d . . . . .
H10A H 0.172781 0.448495 0.212246 0.047 Uiso 1 1 calc GR . . . .
H10B H 0.108397 0.580511 0.277188 0.047 Uiso 1 1 calc GR . . . .
H10C H 0.058221 0.368795 0.258066 0.047 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 1.4454(17) . ?
O1 C2 1.3421(17) . ?
O2 C2 1.2161(17) . ?
O3 C9 1.3406(17) . ?
O3 C10 1.4428(17) . ?
O4 C9 1.2183(16) . ?
N1 H1A 0.8605 . ?
N1 H1B 0.8610 . ?
N1 C6 1.3578(17) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C2 C3 1.4768(18) . ?
C3 C4 1.4038(19) . ?
C3 C8 1.3891(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3692(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.4151(19) . ?
C6 C7 1.4212(18) . ?
C7 C8 1.3984(17) . ?
C7 C9 1.4725(18) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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 O1 C1 115.65(11) . . ?
C9 O3 C10 115.17(11) . . ?
H1A N1 H1B 109.3 . . ?
C6 N1 H1A 109.1 . . ?
C6 N1 H1B 109.6 . . ?
O1 C1 H1C 109.5 . . ?
O1 C1 H1D 109.5 . . ?
O1 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
O1 C2 C3 112.77(11) . . ?
O2 C2 O1 122.42(12) . . ?
O2 C2 C3 124.79(13) . . ?
C4 C3 C2 118.76(12) . . ?
C8 C3 C2 122.51(12) . . ?
C8 C3 C4 118.73(12) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.74(13) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.63(12) . . ?
C6 C5 H5 119.2 . . ?
N1 C6 C5 118.92(12) . . ?
N1 C6 C7 123.38(12) . . ?
C5 C6 C7 117.70(12) . . ?
C6 C7 C9 120.04(11) . . ?
C8 C7 C6 119.67(12) . . ?
C8 C7 C9 120.28(12) . . ?
C3 C8 C7 121.51(12) . . ?
C3 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
O3 C9 C7 113.18(11) . . ?
O4 C9 O3 121.89(13) . . ?
O4 C9 C7 124.93(13) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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 -165.17(13) . . . . ?
O1 C2 C3 C8 13.7(2) . . . . ?
O2 C2 C3 C4 13.2(2) . . . . ?
O2 C2 C3 C8 -167.85(15) . . . . ?
N1 C6 C7 C8 177.70(14) . . . . ?
N1 C6 C7 C9 -1.8(2) . . . . ?
C1 O1 C2 O2 -0.9(2) . . . . ?
C1 O1 C2 C3 177.52(12) . . . . ?
C2 C3 C4 C5 178.98(14) . . . . ?
C2 C3 C8 C7 179.66(13) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C3 C8 C7 -1.4(2) . . . . ?
C4 C5 C6 N1 -179.11(14) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 C8 -1.2(2) . . . . ?
C5 C6 C7 C9 179.26(13) . . . . ?
C6 C7 C8 C3 2.0(2) . . . . ?
C6 C7 C9 O3 170.08(13) . . . . ?
C6 C7 C9 O4 -9.7(2) . . . . ?
C8 C3 C4 C5 0.0(2) . . . . ?
C8 C7 C9 O3 -9.45(19) . . . . ?
C8 C7 C9 O4 170.77(15) . . . . ?
C9 C7 C8 C3 -178.44(13) . . . . ?
C10 O3 C9 O4 0.6(2) . . . . ?
C10 O3 C9 C7 -179.23(13) . . . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zxk-2ad-tcnb-h-120k_auto
_database_code_depnum_ccdc_archive 'CCDC 2314834'
loop_
_audit_author_name
_audit_author_address
'Xiaokai Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2023-12-16 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2023-08-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
'Dimethyl aminoterephthalate, 1,2,4,5-tetracyanobenzene'
_chemical_formula_moiety         'C10 H11 N O4, C10 H2 N4'
_chemical_formula_sum            'C20 H13 N5 O4'
_chemical_formula_weight         387.35
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.5102(2)
_cell_length_b                   7.1433(2)
_cell_length_c                   9.9181(2)
_cell_angle_alpha                95.079(2)
_cell_angle_beta                 90.432(2)
_cell_angle_gamma                97.825(2)
_cell_volume                     455.06(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6649
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      30.6460
_cell_measurement_theta_min      2.0720
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.980
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  36.00   0.50    1.20    --    5.19 -92.00  62.00  114
  2  ω    -21.00  66.00   0.50    1.20    --   -6.68  38.00-140.53  174
  3  ω     14.00  62.00   0.50    1.20    --   -6.68  77.00-120.00   96
  4  ω    -30.00   4.00   0.50    1.20    --   -6.68  77.00-120.00   68
  5  ω    -21.00  65.00   0.50    1.20    --   -6.68  37.00   0.00  172
  6  ω    -21.00  64.00   0.50    1.20    --   -6.68  37.00  60.00  170
  7  ω      8.00  40.00   0.50    1.20    --    5.19  92.00 175.00   64
  8  ω    -21.00  37.00   0.50    1.20    --   -6.68  37.00 120.00  116
  9  ω    -22.00  67.00   0.50    1.20    --   -6.68  19.00-180.00  178
 10  ω    -19.00  17.00   0.50    1.20    --   -6.68 -77.00-150.00   72
 11  ω    -53.00 -27.00   0.50    1.20    --   -6.68 -77.00-150.00   52
 12  ω    -21.00  26.00   0.50    1.20    --   -6.68 -99.00 -90.00   94
 13  ω    -36.00  20.00   0.50    1.20    --   -6.68 -92.00  62.00  112
 14  ω    -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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_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_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.029
_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/[σ²(Fo²)+(0.0445P)²+0.0977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0983
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.3981(5) 0.3783(5) 0.1569(3) 0.0292(8) Uani 1 1 d . . . . .
O2 O 0.3573(5) 0.1507(4) 0.3008(3) 0.0284(7) Uani 1 1 d . . . . .
O O 1.2305(5) 0.0142(4) -0.1542(3) 0.0292(7) Uani 1 1 d . . . . .
O3 O 1.2024(5) -0.2081(5) -0.0081(3) 0.0276(8) Uani 1 1 d . . . . .
C1 C 0.6946(6) -0.0207(6) 0.1771(4) 0.0205(9) Uani 1 1 d . . . . .
H1 H 0.625573 -0.089522 0.245124 0.025 Uiso 0.325(9) 1 calc R U P A 1
C2 C 0.6258(7) 0.1481(6) 0.1372(4) 0.0192(9) Uani 1 1 d . . . . .
C3 C 0.8698(6) -0.0818(6) 0.1115(4) 0.0207(9) Uani 1 1 d . . . . .
H3 H 0.920317 -0.192508 0.137038 0.025 Uiso 1 1 calc R U . . .
C15 C 0.7320(7) 0.2443(6) 0.0339(4) 0.0215(9) Uani 1 1 d . . . . .
H15 H 0.685804 0.356114 0.006808 0.026 Uiso 1 1 calc R U . . .
C5 C 0.9675(7) 0.0157(6) 0.0118(4) 0.0211(9) Uani 1 1 d . . . . .
C6 C 0.9011(6) 0.1795(6) -0.0282(4) 0.0214(9) Uani 1 1 d . . . . .
H6 H 0.970988 0.245789 -0.097177 0.026 Uiso 0.675(9) 1 calc R U P A 2
C7 C 1.1506(7) -0.0569(6) -0.0591(4) 0.0206(9) Uani 1 1 d . . . . .
N3 N 0.5974(10) -0.1227(8) 0.2702(6) 0.0234(13) Uani 0.675(9) 1 d . . P A 2
C9 C 0.4518(7) 0.2209(6) 0.2066(4) 0.0213(9) Uani 1 1 d . . . . .
C10 C 0.8054(7) -0.0823(6) 0.6429(4) 0.0211(8) Uani 1 1 d . . . . .
N N 0.3290(7) 0.3766(6) 0.6439(4) 0.0314(10) Uani 1 1 d . . . . .
C12 C 0.4660(7) 0.2943(6) 0.6266(5) 0.0229(9) Uani 1 1 d . . . . .
C13 C 0.7923(6) 0.2440(6) 0.5116(4) 0.0199(8) Uani 1 1 d . . . . .
C14 C 0.6450(6) 0.0223(6) 0.6682(4) 0.0219(9) Uani 1 1 d . . . . .
H14 H 0.540257 -0.016638 0.729933 0.026 Uiso 1 1 calc R U . . .
N1 N 1.2705(6) -0.2136(6) 0.5082(4) 0.0289(9) Uani 1 1 d . . . . .
C16 C 1.1324(7) -0.1305(6) 0.5287(5) 0.0222(9) Uani 1 1 d . . . . .
C4 C 0.9565(6) 0.1376(6) 0.4870(4) 0.0205(9) Uani 1 1 d . . . . .
H4 H 1.062160 0.176694 0.425938 0.025 Uiso 1 1 calc R U . . .
N18 N 0.8212(7) -0.3850(6) 0.7660(4) 0.0305(9) Uani 1 1 d . . . . .
N2 N 0.7794(6) 0.5460(5) 0.3875(4) 0.0274(8) Uani 1 1 d . . . . .
C1A C 0.6378(6) 0.1862(6) 0.6023(4) 0.0204(9) Uani 1 1 d . . . . .
C1B C 0.9630(6) -0.0241(6) 0.5523(4) 0.0207(9) Uani 1 1 d . . . . .
C1C C 0.7856(7) 0.4116(7) 0.4448(5) 0.0235(9) Uani 1 1 d . . . . .
C C 0.2325(8) 0.4581(7) 0.2283(5) 0.0327(12) Uani 1 1 d . . . . .
HA H 0.219646 0.582529 0.197134 0.049 Uiso 1 1 calc R U . . .
HB H 0.263903 0.472496 0.325727 0.049 Uiso 1 1 calc R U . . .
HC H 0.101821 0.373390 0.210254 0.049 Uiso 1 1 calc R U . . .
C8 C 1.3665(8) -0.2941(7) -0.0790(5) 0.0330(12) Uani 1 1 d . . . . .
H8A H 1.323545 -0.330998 -0.173625 0.049 Uiso 1 1 calc R U . . .
H8B H 1.392847 -0.406704 -0.035498 0.049 Uiso 1 1 calc R U . . .
H8C H 1.493373 -0.202462 -0.075537 0.049 Uiso 1 1 calc R U . . .
C11 C 0.8148(7) -0.2525(6) 0.7124(5) 0.0213(8) Uani 1 1 d . . . . .
N4 N 1.001(2) 0.286(2) -0.1237(14) 0.029(3) Uani 0.325(9) 1 d . U P A 1
H4A H 0.956734 0.391930 -0.143080 0.035 Uiso 0.325(9) 1 calc R U P A 1
H4B H 1.109593 0.248857 -0.165088 0.035 Uiso 0.325(9) 1 calc R U P A 1
H3A H 0.494(7) -0.097(7) 0.304(5) 0.030(12) Uiso 0.675(9) 1 d . . P A 2
H3B H 0.647(7) -0.218(7) 0.290(5) 0.028(12) Uiso 0.675(9) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C9 1.354(5) . ?
O1 C 1.447(5) . ?
O2 C9 1.229(5) . ?
O C7 1.199(5) . ?
O3 C7 1.315(5) . ?
O3 C8 1.458(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.428(6) . ?
C1 C3 1.418(5) . ?
C1 N3 1.337(7) . ?
C2 C15 1.416(5) . ?
C2 C9 1.462(5) . ?
C3 H3 0.9500 . ?
C3 C5 1.370(6) . ?
C15 H15 0.9500 . ?
C15 C6 1.380(5) . ?
C5 C6 1.390(6) . ?
C5 C7 1.516(5) . ?
C6 H6 0.9500 . ?
C6 N4 1.380(13) . ?
N3 H3A 0.79(5) . ?
N3 H3B 0.83(5) . ?
C10 C14 1.376(6) . ?
C10 C1B 1.413(6) . ?
C10 C11 1.458(6) . ?
N C12 1.139(6) . ?
C12 C1A 1.453(5) . ?
C13 C4 1.404(5) . ?
C13 C1A 1.399(6) . ?
C13 C1C 1.424(6) . ?
C14 H14 0.9500 . ?
C14 C1A 1.396(6) . ?
N1 C16 1.153(6) . ?
C16 C1B 1.431(6) . ?
C4 H4 0.9500 . ?
C4 C1B 1.378(6) . ?
N18 C11 1.131(6) . ?
N2 C1C 1.163(6) . ?
C HA 0.9800 . ?
C HB 0.9800 . ?
C HC 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?

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
C9 O1 C 114.5(3) . . ?
C7 O3 C8 115.1(3) . . ?
C2 C1 H1 121.2 . . ?
C3 C1 H1 121.2 . . ?
C3 C1 C2 117.6(4) . . ?
N3 C1 C2 122.4(5) . . ?
N3 C1 C3 120.0(4) . . ?
C1 C2 C9 119.4(4) . . ?
C15 C2 C1 119.1(4) . . ?
C15 C2 C9 121.5(4) . . ?
C1 C3 H3 119.4 . . ?
C5 C3 C1 121.2(4) . . ?
C5 C3 H3 119.4 . . ?
C2 C15 H15 119.2 . . ?
C6 C15 C2 121.5(4) . . ?
C6 C15 H15 119.2 . . ?
C3 C5 C6 121.6(4) . . ?
C3 C5 C7 119.8(4) . . ?
C6 C5 C7 118.6(4) . . ?
C15 C6 C5 118.9(4) . . ?
C15 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N4 C6 C15 117.8(7) . . ?
N4 C6 C5 123.2(7) . . ?
O C7 O3 125.2(4) . . ?
O C7 C5 122.4(4) . . ?
O3 C7 C5 112.4(3) . . ?
C1 N3 H3A 122(4) . . ?
C1 N3 H3B 118(3) . . ?
H3A N3 H3B 120(5) . . ?
O1 C9 C2 113.6(3) . . ?
O2 C9 O1 120.9(4) . . ?
O2 C9 C2 125.5(4) . . ?
C14 C10 C1B 120.6(4) . . ?
C14 C10 C11 119.6(4) . . ?
C1B C10 C11 119.7(4) . . ?
N C12 C1A 178.7(4) . . ?
C4 C13 C1C 119.6(4) . . ?
C1A C13 C4 120.0(4) . . ?
C1A C13 C1C 120.4(4) . . ?
C10 C14 H14 120.3 . . ?
C10 C14 C1A 119.4(4) . . ?
C1A C14 H14 120.3 . . ?
N1 C16 C1B 178.8(5) . . ?
C13 C4 H4 120.3 . . ?
C1B C4 C13 119.4(4) . . ?
C1B C4 H4 120.3 . . ?
C13 C1A C12 120.2(4) . . ?
C14 C1A C12 119.4(4) . . ?
C14 C1A C13 120.4(4) . . ?
C10 C1B C16 120.5(4) . . ?
C4 C1B C10 120.2(4) . . ?
C4 C1B C16 119.3(4) . . ?
N2 C1C C13 178.5(5) . . ?
O1 C HA 109.5 . . ?
O1 C HB 109.5 . . ?
O1 C HC 109.5 . . ?
HA C HB 109.5 . . ?
HA C HC 109.5 . . ?
HB C HC 109.5 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N18 C11 C10 179.7(6) . . ?
C6 N4 H4A 120.0 . . ?
C6 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?

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
C1 C2 C15 C6 -0.5(6) . . . . ?
C1 C2 C9 O1 -178.3(4) . . . . ?
C1 C2 C9 O2 1.3(7) . . . . ?
C1 C3 C5 C6 0.7(6) . . . . ?
C1 C3 C5 C7 -178.2(4) . . . . ?
C2 C1 C3 C5 -1.0(5) . . . . ?
C2 C15 C6 C5 0.1(5) . . . . ?
C2 C15 C6 N4 -177.2(9) . . . . ?
C3 C1 C2 C15 0.9(6) . . . . ?
C3 C1 C2 C9 -177.2(4) . . . . ?
C3 C5 C6 C15 -0.3(6) . . . . ?
C3 C5 C6 N4 176.9(8) . . . . ?
C3 C5 C7 O 173.7(5) . . . . ?
C3 C5 C7 O3 -3.5(5) . . . . ?
C15 C2 C9 O1 3.7(6) . . . . ?
C15 C2 C9 O2 -176.7(5) . . . . ?
C6 C5 C7 O -5.3(6) . . . . ?
C6 C5 C7 O3 177.5(4) . . . . ?
C7 C5 C6 C15 178.7(3) . . . . ?
C7 C5 C6 N4 -4.1(10) . . . . ?
N3 C1 C2 C15 -177.5(5) . . . . ?
N3 C1 C2 C9 4.4(7) . . . . ?
N3 C1 C3 C5 177.4(5) . . . . ?
C9 C2 C15 C6 177.6(4) . . . . ?
C10 C14 C1A C12 178.6(4) . . . . ?
C10 C14 C1A C13 -0.2(6) . . . . ?
C13 C4 C1B C10 0.1(6) . . . . ?
C13 C4 C1B C16 -178.9(4) . . . . ?
C14 C10 C1B C16 178.4(4) . . . . ?
C14 C10 C1B C4 -0.6(6) . . . . ?
C4 C13 C1A C12 -179.1(4) . . . . ?
C4 C13 C1A C14 -0.3(6) . . . . ?
C1A C13 C4 C1B 0.3(5) . . . . ?
C1B C10 C14 C1A 0.7(6) . . . . ?
C1C C13 C4 C1B 179.7(4) . . . . ?
C1C C13 C1A C12 1.5(6) . . . . ?
C1C C13 C1A C14 -179.7(4) . . . . ?
C O1 C9 O2 3.2(7) . . . . ?
C O1 C9 C2 -177.2(4) . . . . ?
C8 O3 C7 O -1.9(7) . . . . ?
C8 O3 C7 C5 175.2(4) . . . . ?
C11 C10 C14 C1A 179.4(4) . . . . ?
C11 C10 C1B C16 -0.3(6) . . . . ?
C11 C10 C1B C4 -179.4(4) . . . . ?

_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
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r20230608c_autored
_database_code_depnum_ccdc_archive 'CCDC 2314833'
loop_
_audit_author_name
_audit_author_address
'Xiaokai Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2023-12-16 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2023-06-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'Dimethyl aminoterephthalate,1,2,4,5-tetracyanobenzene'
_chemical_formula_moiety         '2(C10 H11 N O4), C10 H2 N4'
_chemical_formula_sum            'C30 H24 N6 O8'
_chemical_formula_weight         596.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7011(2)
_cell_length_b                   9.6663(2)
_cell_length_c                   11.8016(3)
_cell_angle_alpha                100.928(2)
_cell_angle_beta                 98.038(2)
_cell_angle_gamma                106.164(2)
_cell_volume                     705.72(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8149
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.2080
_cell_measurement_theta_min      2.2440
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.973
_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_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             310
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4059
_reflns_number_total             5494
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.048
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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 . . . ?

_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
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r20230610b_autored
_database_code_depnum_ccdc_archive 'CCDC 2314835'
loop_
_audit_author_name
_audit_author_address
'Xiaokai Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2023-12-16 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2023-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'dimethyl 5-aminoisophthalate, 1,2,4,5-tetracyanobenzene'
_chemical_formula_moiety         '2(C10 H11 N O4), C10 H2 N4'
_chemical_formula_sum            'C30 H24 N6 O8'
_chemical_formula_weight         596.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.6502(3)
_cell_length_b                   22.7523(7)
_cell_length_c                   18.2160(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.461(3)
_cell_angle_gamma                90
_cell_volume                     3107.45(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11656
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      35.5930
_cell_measurement_theta_min      2.1080
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            49760
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.282
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   0.50    8.00    --  -30.00   0.00 180.00  360
  2  ω   -120.00  60.00   0.50    8.00    --  -30.00   0.00   0.00  360
  3  ω    -66.00  60.00   0.50    8.00    --  -30.00  70.00 180.00  252
  4  ω   -120.00   6.00   0.50    8.00    --  -30.00 -70.00 180.00  252
  5  ω    -66.00  54.00   0.50    8.00    --  -30.00  70.00   0.00  240
  6  ω    -66.00  52.00   0.50    8.00    --  -30.00  70.00  90.00  236
;
_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      -0.0354817000
_diffrn_orient_matrix_UB_12      -0.0033278000
_diffrn_orient_matrix_UB_13      -0.0388156000
_diffrn_orient_matrix_UB_21      -0.0297112000
_diffrn_orient_matrix_UB_22      -0.0286662000
_diffrn_orient_matrix_UB_23      0.0066755000
_diffrn_orient_matrix_UB_31      -0.0825012000
_diffrn_orient_matrix_UB_32      0.0117837000
_diffrn_orient_matrix_UB_33      0.0052547000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4272
_reflns_number_total             6360
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0891
_refine_ls_restrained_S_all      1.035
_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)+(0.1431P)²+1.6733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2337
_refine_ls_wR_factor_ref         0.2585
_refine_special_details          ?
_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), N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C11(H11), C13(H13), C15(H15), C23(H23), C26(H26)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.1656(3) 0.92046(9) 0.27096(11) 0.0360(5) Uani 1 1 d . . . . .
O2 O -0.0104(3) 0.83846(9) 0.30576(11) 0.0369(5) Uani 1 1 d . . . . .
O3 O -0.5831(3) 0.92706(9) 0.03234(11) 0.0365(5) Uani 1 1 d . . . . .
O4 O -0.6927(3) 0.84413(10) -0.02467(12) 0.0411(6) Uani 1 1 d . . . . .
N1 N -0.3500(3) 0.68331(11) 0.13533(14) 0.0359(6) Uani 1 1 d . . . . .
H1A H -0.430201 0.668999 0.157589 0.043 Uiso 1 1 d R U . . .
H1B H -0.373005 0.672319 0.089045 0.043 Uiso 1 1 d R U . . .
C1 C -0.3653(3) 0.86785(12) 0.14641(14) 0.0248(6) Uani 1 1 d . . . . .
H1 H -0.370371 0.909472 0.149478 0.030 Uiso 1 1 calc R U . . .
C2 C -0.2466(3) 0.83498(12) 0.19985(14) 0.0255(6) Uani 1 1 d . . . . .
C3 C -0.2394(3) 0.77449(12) 0.19414(15) 0.0262(6) Uani 1 1 d . . . . .
H3 H -0.154789 0.753293 0.229610 0.031 Uiso 1 1 calc R U . . .
C4 C -0.3526(4) 0.74380(12) 0.13786(15) 0.0283(6) Uani 1 1 d . . . . .
C5 C -0.4726(3) 0.77661(13) 0.08477(15) 0.0272(6) Uani 1 1 d . . . . .
H5 H -0.552268 0.756921 0.045896 0.033 Uiso 1 1 calc R U . . .
C6 C -0.4753(3) 0.83722(13) 0.08880(15) 0.0278(6) Uani 1 1 d . . . . .
C7 C -0.0613(4) 0.95002(14) 0.33530(17) 0.0440(8) Uani 1 1 d . . . . .
H7A H 0.065189 0.948538 0.332495 0.066 Uiso 1 1 calc R U . . .
H7B H -0.078918 0.930460 0.381216 0.066 Uiso 1 1 calc R U . . .
H7C H -0.099614 0.991099 0.335798 0.066 Uiso 1 1 calc R U . . .
C8 C -0.1277(3) 0.86387(12) 0.26384(14) 0.0274(6) Uani 1 1 d . . . . .
C9 C -0.6921(4) 0.95911(16) -0.02915(18) 0.0429(8) Uani 1 1 d . . . . .
H9A H -0.651019 0.950523 -0.075666 0.064 Uiso 1 1 calc R U . . .
H9B H -0.681745 1.001382 -0.018877 0.064 Uiso 1 1 calc R U . . .
H9C H -0.816918 0.947054 -0.034403 0.064 Uiso 1 1 calc R U . . .
C10 C -0.5947(4) 0.86845(14) 0.02703(15) 0.0308(6) Uani 1 1 d . . . . .
O5 O -0.0162(2) 0.93284(8) 0.06519(10) 0.0299(5) Uani 1 1 d . . . . .
O6 O 0.1075(3) 0.85045(9) 0.11839(10) 0.0344(5) Uani 1 1 d . . . . .
O7 O -0.4298(2) 0.92829(8) -0.17227(11) 0.0330(5) Uani 1 1 d . . . . .
O8 O -0.5688(3) 0.84508(9) -0.21545(11) 0.0380(5) Uani 1 1 d . . . . .
N2 N -0.2259(3) 0.68905(10) -0.04451(12) 0.0304(6) Uani 1 1 d . . . . .
H2A H -0.202471 0.677251 0.001303 0.036 Uiso 1 1 d R U . . .
H2B H -0.329054 0.676101 -0.066146 0.036 Uiso 1 1 d R U . . .
C11 C -0.2228(3) 0.87357(12) -0.05159(13) 0.0220(5) Uani 1 1 d . . . . .
H11 H -0.220828 0.915280 -0.053734 0.026 Uiso 1 1 calc R U . . .
C12 C -0.1113(3) 0.84340(11) 0.00598(14) 0.0233(6) Uani 1 1 d . . . . .
C13 C -0.1118(3) 0.78252(12) 0.00775(14) 0.0244(6) Uani 1 1 d . . . . .
H13 H -0.031432 0.762617 0.046203 0.029 Uiso 1 1 calc R U . . .
C14 C -0.2281(3) 0.74975(12) -0.04590(14) 0.0255(6) Uani 1 1 d . . . . .
C15 C -0.3434(3) 0.78020(12) -0.10262(14) 0.0239(6) Uani 1 1 d . . . . .
H15 H -0.426094 0.759047 -0.138902 0.029 Uiso 1 1 calc R U . . .
C16 C -0.3375(3) 0.84114(12) -0.10612(14) 0.0232(6) Uani 1 1 d . . . . .
C17 C 0.0894(4) 0.96525(13) 0.12716(16) 0.0352(7) Uani 1 1 d . . . . .
H17A H 0.071063 1.007509 0.118482 0.053 Uiso 1 1 calc R U . . .
H17B H 0.215884 0.955841 0.131000 0.053 Uiso 1 1 calc R U . . .
H17C H 0.052441 0.954272 0.173829 0.053 Uiso 1 1 calc R U . . .
C18 C 0.0050(3) 0.87473(12) 0.06865(14) 0.0242(6) Uani 1 1 d . . . . .
C19 C -0.5359(4) 0.95921(14) -0.23521(18) 0.0434(8) Uani 1 1 d . . . . .
H19A H -0.518962 0.940969 -0.282042 0.065 Uiso 1 1 calc R U . . .
H19B H -0.498301 1.000427 -0.234159 0.065 Uiso 1 1 calc R U . . .
H19C H -0.662096 0.957140 -0.232023 0.065 Uiso 1 1 calc R U . . .
C20 C -0.4578(3) 0.87058(12) -0.16998(15) 0.0265(6) Uani 1 1 d . . . . .
N3 N -0.7079(3) 0.67437(13) -0.04158(16) 0.0465(7) Uani 1 1 d . . . . .
N4 N -1.0824(4) 0.58008(13) -0.16898(19) 0.0541(8) Uani 1 1 d . . . . .
N5 N -1.3863(4) 0.82882(14) -0.37428(17) 0.0506(8) Uani 1 1 d . . . . .
N6 N -1.0160(4) 0.92357(13) -0.23920(18) 0.0546(8) Uani 1 1 d . . . . .
C21 C -0.9298(4) 0.72532(14) -0.14759(16) 0.0331(7) Uani 1 1 d . . . . .
C22 C -1.0613(4) 0.69145(13) -0.19464(17) 0.0329(7) Uani 1 1 d . . . . .
C23 C -1.1792(4) 0.71834(14) -0.25248(16) 0.0362(7) Uani 1 1 d . . . . .
H23 H -1.269485 0.695752 -0.283319 0.043 Uiso 1 1 calc R U . . .
C24 C -1.1661(4) 0.77765(13) -0.26544(16) 0.0315(6) Uani 1 1 d . . . . .
C25 C -1.0341(4) 0.81199(13) -0.21864(16) 0.0335(7) Uani 1 1 d . . . . .
C26 C -0.9163(4) 0.78493(13) -0.16059(16) 0.0330(7) Uani 1 1 d . . . . .
H26 H -0.825952 0.807454 -0.129683 0.040 Uiso 1 1 calc R U . . .
C27 C -0.8066(4) 0.69759(14) -0.08744(18) 0.0391(7) Uani 1 1 d . . . . .
C28 C -1.0746(4) 0.62935(15) -0.18042(18) 0.0419(8) Uani 1 1 d . . . . .
C29 C -1.2881(4) 0.80591(15) -0.32575(19) 0.0408(8) Uani 1 1 d . . . . .
C30 C -1.0240(4) 0.87400(14) -0.23107(17) 0.0353(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C7 1.446(3) . ?
O1 C8 1.332(3) . ?
O2 C8 1.204(3) . ?
O3 C9 1.453(3) . ?
O3 C10 1.339(4) . ?
O4 C10 1.214(3) . ?
N1 H1A 0.8637 . ?
N1 H1B 0.8633 . ?
N1 C4 1.377(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.407(3) . ?
C1 C6 1.394(4) . ?
C2 C3 1.382(4) . ?
C2 C8 1.482(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(4) . ?
C4 C5 1.408(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(4) . ?
C6 C10 1.482(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O5 C17 1.452(3) . ?
O5 C18 1.332(3) . ?
O6 C18 1.208(3) . ?
O7 C19 1.449(3) . ?
O7 C20 1.332(3) . ?
O8 C20 1.210(3) . ?
N2 H2A 0.8609 . ?
N2 H2B 0.8612 . ?
N2 C14 1.381(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(3) . ?
C11 C16 1.398(3) . ?
C12 C13 1.385(4) . ?
C12 C18 1.483(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.399(4) . ?
C14 C15 1.401(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(4) . ?
C16 C20 1.491(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N3 C27 1.138(4) . ?
N4 C28 1.144(4) . ?
N5 C29 1.163(4) . ?
N6 C30 1.141(4) . ?
C21 C22 1.413(4) . ?
C21 C26 1.384(4) . ?
C21 C27 1.441(4) . ?
C22 C23 1.386(4) . ?
C22 C28 1.444(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.377(4) . ?
C24 C25 1.419(4) . ?
C24 C29 1.444(4) . ?
C25 C26 1.390(4) . ?
C25 C30 1.433(4) . ?
C26 H26 0.9500 . ?

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
C8 O1 C7 115.6(2) . . ?
C10 O3 C9 115.1(2) . . ?
H1A N1 H1B 108.9 . . ?
C4 N1 H1A 110.2 . . ?
C4 N1 H1B 108.7 . . ?
C2 C1 H1 121.1 . . ?
C6 C1 H1 121.1 . . ?
C6 C1 C2 117.7(3) . . ?
C1 C2 C8 121.3(2) . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 C8 118.2(2) . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
N1 C4 C3 121.0(2) . . ?
N1 C4 C5 121.2(3) . . ?
C3 C4 C5 117.7(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C10 121.4(3) . . ?
C5 C6 C1 121.7(2) . . ?
C5 C6 C10 116.9(2) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C2 113.2(2) . . ?
O2 C8 O1 123.5(2) . . ?
O2 C8 C2 123.3(3) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 C6 113.6(2) . . ?
O4 C10 O3 122.1(3) . . ?
O4 C10 C6 124.2(3) . . ?
C18 O5 C17 115.1(2) . . ?
C20 O7 C19 115.8(2) . . ?
H2A N2 H2B 109.4 . . ?
C14 N2 H2A 109.2 . . ?
C14 N2 H2B 109.1 . . ?
C12 C11 H11 120.7 . . ?
C12 C11 C16 118.6(2) . . ?
C16 C11 H11 120.7 . . ?
C11 C12 C18 121.7(2) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 C18 117.8(2) . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
N2 C14 C13 121.1(2) . . ?
N2 C14 C15 120.8(2) . . ?
C13 C14 C15 118.1(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C20 121.3(2) . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 C20 117.6(2) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C18 C12 113.1(2) . . ?
O6 C18 O5 123.0(2) . . ?
O6 C18 C12 123.9(3) . . ?
O7 C19 H19A 109.5 . . ?
O7 C19 H19B 109.5 . . ?
O7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O7 C20 C16 112.9(2) . . ?
O8 C20 O7 123.1(2) . . ?
O8 C20 C16 124.0(3) . . ?
C22 C21 C27 120.1(3) . . ?
C26 C21 C22 119.9(3) . . ?
C26 C21 C27 119.9(3) . . ?
C21 C22 C28 119.5(3) . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 C28 120.7(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 C29 120.6(3) . . ?
C25 C24 C29 119.1(3) . . ?
C24 C25 C30 120.1(3) . . ?
C26 C25 C24 119.3(3) . . ?
C26 C25 C30 120.6(3) . . ?
C21 C26 C25 120.3(3) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
N3 C27 C21 177.7(4) . . ?
N4 C28 C22 179.0(3) . . ?
N5 C29 C24 179.8(4) . . ?
N6 C30 C25 178.4(3) . . ?

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
N1 C4 C5 C6 179.0(2) . . . . ?
C1 C2 C3 C4 -2.6(4) . . . . ?
C1 C2 C8 O1 9.9(4) . . . . ?
C1 C2 C8 O2 -171.2(3) . . . . ?
C1 C6 C10 O3 0.9(4) . . . . ?
C1 C6 C10 O4 179.7(3) . . . . ?
C2 C1 C6 C5 1.7(4) . . . . ?
C2 C1 C6 C10 -175.5(2) . . . . ?
C2 C3 C4 N1 -176.5(3) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
C3 C2 C8 O1 -169.6(2) . . . . ?
C3 C2 C8 O2 9.4(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 -2.4(4) . . . . ?
C4 C5 C6 C10 174.9(2) . . . . ?
C5 C6 C10 O3 -176.4(2) . . . . ?
C5 C6 C10 O4 2.4(4) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C6 C1 C2 C8 -178.7(2) . . . . ?
C7 O1 C8 O2 -2.8(4) . . . . ?
C7 O1 C8 C2 176.2(2) . . . . ?
C8 C2 C3 C4 176.8(2) . . . . ?
C9 O3 C10 O4 -1.7(4) . . . . ?
C9 O3 C10 C6 177.2(2) . . . . ?
N2 C14 C15 C16 -176.2(2) . . . . ?
C11 C12 C13 C14 -2.6(4) . . . . ?
C11 C12 C18 O5 3.0(3) . . . . ?
C11 C12 C18 O6 -177.6(2) . . . . ?
C11 C16 C20 O7 6.1(3) . . . . ?
C11 C16 C20 O8 -174.2(3) . . . . ?
C12 C11 C16 C15 1.2(4) . . . . ?
C12 C11 C16 C20 -178.8(2) . . . . ?
C12 C13 C14 N2 178.9(2) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C13 C12 C18 O5 -174.3(2) . . . . ?
C13 C12 C18 O6 5.0(4) . . . . ?
C13 C14 C15 C16 1.8(4) . . . . ?
C14 C15 C16 C11 -2.9(4) . . . . ?
C14 C15 C16 C20 177.1(2) . . . . ?
C15 C16 C20 O7 -173.9(2) . . . . ?
C15 C16 C20 O8 5.8(4) . . . . ?
C16 C11 C12 C13 1.6(4) . . . . ?
C16 C11 C12 C18 -175.7(2) . . . . ?
C17 O5 C18 O6 -1.9(4) . . . . ?
C17 O5 C18 C12 177.5(2) . . . . ?
C18 C12 C13 C14 174.8(2) . . . . ?
C19 O7 C20 O8 -2.7(4) . . . . ?
C19 O7 C20 C16 176.9(2) . . . . ?
C21 C22 C23 C24 1.6(4) . . . . ?
C22 C21 C26 C25 1.6(4) . . . . ?
C22 C23 C24 C25 -1.4(4) . . . . ?
C22 C23 C24 C29 179.8(3) . . . . ?
C23 C24 C25 C26 1.2(4) . . . . ?
C23 C24 C25 C30 -178.3(3) . . . . ?
C24 C25 C26 C21 -1.3(4) . . . . ?
C26 C21 C22 C23 -1.7(4) . . . . ?
C26 C21 C22 C28 -179.8(3) . . . . ?
C27 C21 C22 C23 -179.9(3) . . . . ?
C27 C21 C22 C28 2.0(4) . . . . ?
C27 C21 C26 C25 179.8(3) . . . . ?
C28 C22 C23 C24 179.7(3) . . . . ?
C29 C24 C25 C26 -179.9(3) . . . . ?
C29 C24 C25 C30 0.5(4) . . . . ?
C30 C25 C26 C21 178.2(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.263 0.000 0.500 208.1 46.3 ?
2 -0.319 0.500 0.000 208.1 46.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 4.291
_oxdiff_exptl_absorpt_empirical_full_min 0.452
_exptl_crystal_preparation       Luminescent
