# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_tx256
_database_code_depnum_ccdc_archive 'CCDC 1893131'
loop_
_audit_author_name
_audit_author_address
D-ND
;Institute of Chemistry, CAS
China
;
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-03-19 downloaded from the CCDC.
;
_audit_creation_date             2019-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_formula_moiety         'C38 H32 N4'
_chemical_formula_sum            'C38 H32 N4'
_chemical_formula_weight         544.67
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHN
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.03220(10)
_cell_length_b                   12.26750(10)
_cell_length_c                   25.1471(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2786.36(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      74.8220
_cell_measurement_theta_min      3.5120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.031
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18177
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.469
_diffrn_reflns_theta_min         3.515
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     75.00 116.00   0.50    3.00    --  103.25 -30.00  60.00   82
  2  ω     95.00 132.00   0.50    3.00    --  103.25  25.00  82.00   74
  3  ω     47.00  73.00   0.50    3.00    --  103.25 -30.00  60.00   52
  4  ω     33.00  83.00   0.50    3.00    --  103.25 -45.00  90.00  100
  5  ω     36.00  82.00   0.50    2.00    --   47.45  25.00  82.00   92
  6  ω     36.00 116.00   0.50    3.00    --  103.25 -30.00 150.00  160
  7  ω     28.00 111.00   0.50    3.00    --  103.25 -25.00 -81.00  166
  8  ω     64.00 109.00   0.50    3.00    --  103.25 -94.00-120.00   90
  9  ω     33.00  60.00   0.50    3.00    --  103.25 -94.00-120.00   54
 10  ω     18.00  94.00   0.50    2.00    --   47.45-125.00-180.00  152
 11  ω     -7.00  18.00   0.50    2.00    --   47.45 -25.00 -81.00   50
 12  ω    -50.00  22.00   0.50    2.00    --  -47.45  25.00  82.00  144
 13  ω    -56.00 -29.00   0.50    3.00    --  -99.00 125.00 120.00   54
 14  ω    -97.00 -70.00   0.50    3.00    --  -99.00 125.00 120.00   54
 15  ω   -106.00 -69.00   0.50    3.00    --  -99.00  25.00  82.00   74
 16  ω   -122.00 -34.00   0.50    2.00    --  -47.45 -25.00 -81.00  176
 17  ω   -111.00 -37.00   0.50    3.00    --  -99.00  45.00 -60.00  148
 18  ω   -151.00 -90.00   0.50    3.00    --  -99.00 -25.00 -81.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0223603000
_diffrn_orient_matrix_UB_12      -0.0408274000
_diffrn_orient_matrix_UB_13      0.0573759000
_diffrn_orient_matrix_UB_21      0.1688998000
_diffrn_orient_matrix_UB_22      0.0000666000
_diffrn_orient_matrix_UB_23      -0.0084526000
_diffrn_orient_matrix_UB_31      0.0076842000
_diffrn_orient_matrix_UB_32      0.1187467000
_diffrn_orient_matrix_UB_33      0.0197744000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                5014
_reflns_number_total             5482
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 2009 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.074
_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)+(0.0475P)²+0.6145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0973
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26), C27(H27), C28(H28),
  C33(H33), C34(H34), C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N1 N 0.1461(2) 0.44950(15) 0.83960(8) 0.0327(4) Uani 1 1 d . . . . .
N2 N 0.3197(2) 0.46054(15) 0.77226(7) 0.0308(4) Uani 1 1 d . . . . .
N3 N 0.4870(2) 0.45869(15) 0.70327(8) 0.0316(4) Uani 1 1 d . . . . .
N4 N 0.6487(2) 0.45022(16) 0.63042(7) 0.0338(4) Uani 1 1 d . . . . .
C1 C 0.2509(2) 0.5134(2) 0.81056(9) 0.0314(5) Uani 1 1 d . . . . .
C2 C 0.2766(3) 0.6232(2) 0.82372(10) 0.0357(5) Uani 1 1 d . . . . .
H2 H 0.228796 0.655285 0.852486 0.043 Uiso 1 1 calc R . . . .
C3 C 0.3737(3) 0.68167(19) 0.79321(10) 0.0354(5) Uani 1 1 d . . . . .
H3 H 0.391371 0.754843 0.800483 0.042 Uiso 1 1 calc R . . . .
C4 C 0.4463(2) 0.62984(18) 0.75075(9) 0.0316(5) Uani 1 1 d . . . . .
C5 C 0.4182(2) 0.51757(18) 0.74232(9) 0.0303(5) Uani 1 1 d . . . . .
C6 C 0.5801(2) 0.51142(19) 0.67272(9) 0.0329(5) Uani 1 1 d . . . . .
C7 C 0.6149(3) 0.6232(2) 0.67779(10) 0.0384(5) Uani 1 1 d . . . . .
H7 H 0.682199 0.655771 0.654759 0.046 Uiso 1 1 calc R . . . .
C8 C 0.5488(3) 0.68233(19) 0.71669(10) 0.0355(5) Uani 1 1 d . . . . .
H8 H 0.570454 0.755937 0.720928 0.043 Uiso 1 1 calc R . . . .
C9 C 0.5857(3) 0.46214(18) 0.57942(9) 0.0327(5) Uani 1 1 d . . . . .
C10 C 0.4409(3) 0.5015(2) 0.57496(10) 0.0391(5) Uani 1 1 d . . . . .
H10 H 0.386925 0.517165 0.605505 0.047 Uiso 1 1 calc R . . . .
C11 C 0.3773(3) 0.5172(2) 0.52561(11) 0.0434(6) Uani 1 1 d . . . . .
H11 H 0.281549 0.544566 0.523023 0.052 Uiso 1 1 calc R . . . .
C12 C 0.4554(3) 0.4925(2) 0.48043(11) 0.0454(6) Uani 1 1 d . . . . .
H12 H 0.412896 0.503153 0.447151 0.054 Uiso 1 1 calc R . . . .
C13 C 0.5982(3) 0.4515(2) 0.48459(10) 0.0423(6) Uani 1 1 d . . . . .
H13 H 0.649948 0.434167 0.453758 0.051 Uiso 1 1 calc R . . . .
C14 C 0.6658(3) 0.43563(19) 0.53363(10) 0.0349(5) Uani 1 1 d . . . . .
C15 C 0.8200(3) 0.3851(2) 0.53621(11) 0.0407(6) Uani 1 1 d . . . . .
C16 C 0.8875(3) 0.39939(19) 0.59113(10) 0.0357(5) Uani 1 1 d . . . . .
C17 C 0.8016(3) 0.42753(18) 0.63567(10) 0.0328(5) Uani 1 1 d . . . . .
C18 C 0.8660(3) 0.4310(2) 0.68625(10) 0.0376(5) Uani 1 1 d . . . . .
H18 H 0.807867 0.447033 0.715744 0.045 Uiso 1 1 calc R . . . .
C19 C 1.0160(3) 0.4107(2) 0.69270(11) 0.0408(6) Uani 1 1 d . . . . .
H19 H 1.058295 0.414587 0.726355 0.049 Uiso 1 1 calc R . . . .
C20 C 1.1023(3) 0.3848(2) 0.64938(11) 0.0434(6) Uani 1 1 d . . . . .
H20 H 1.203089 0.371846 0.653500 0.052 Uiso 1 1 calc R . . . .
C21 C 1.0378(3) 0.3784(2) 0.60000(12) 0.0441(6) Uani 1 1 d . . . . .
H21 H 1.096670 0.359213 0.571150 0.053 Uiso 1 1 calc R . . . .
C22 C 0.8050(4) 0.2626(2) 0.52533(15) 0.0640(9) Uani 1 1 d . . . . .
H22A H 0.736870 0.231176 0.550313 0.096 Uiso 1 1 calc GR . . . .
H22B H 0.899931 0.228283 0.529003 0.096 Uiso 1 1 calc GR . . . .
H22C H 0.768657 0.251648 0.489847 0.096 Uiso 1 1 calc GR . . . .
C23 C 0.9210(3) 0.4363(3) 0.49351(12) 0.0599(8) Uani 1 1 d . . . . .
H23A H 0.877745 0.425837 0.459021 0.090 Uiso 1 1 calc GR . . . .
H23B H 1.016560 0.402156 0.494615 0.090 Uiso 1 1 calc GR . . . .
H23C H 0.931545 0.512947 0.500338 0.090 Uiso 1 1 calc GR . . . .
C24 C -0.0074(2) 0.47287(19) 0.83742(9) 0.0313(5) Uani 1 1 d . . . . .
C25 C -0.0610(3) 0.5743(2) 0.82203(10) 0.0379(5) Uani 1 1 d . . . . .
H25 H 0.004511 0.628131 0.810942 0.045 Uiso 1 1 calc R . . . .
C26 C -0.2112(3) 0.5955(2) 0.82311(11) 0.0421(6) Uani 1 1 d . . . . .
H26 H -0.246457 0.663135 0.812194 0.050 Uiso 1 1 calc R . . . .
C27 C -0.3090(3) 0.5167(2) 0.84032(11) 0.0436(6) Uani 1 1 d . . . . .
H27 H -0.409627 0.532091 0.842735 0.052 Uiso 1 1 calc R . . . .
C28 C -0.2565(3) 0.4151(2) 0.85390(11) 0.0411(6) Uani 1 1 d . . . . .
H28 H -0.323382 0.361678 0.864478 0.049 Uiso 1 1 calc R . . . .
C29 C -0.1065(3) 0.38974(19) 0.85229(9) 0.0344(5) Uani 1 1 d . . . . .
C30 C -0.0461(3) 0.27514(19) 0.86145(10) 0.0372(5) Uani 1 1 d . . . . .
C31 C 0.1004(3) 0.28580(19) 0.89099(9) 0.0338(5) Uani 1 1 d . . . . .
C32 C 0.1974(3) 0.36912(18) 0.87529(9) 0.0321(5) Uani 1 1 d . . . . .
C33 C 0.3384(3) 0.3763(2) 0.89731(10) 0.0378(5) Uani 1 1 d . . . . .
H33 H 0.402831 0.430869 0.886195 0.045 Uiso 1 1 calc R . . . .
C34 C 0.3833(3) 0.3022(2) 0.93582(11) 0.0433(6) Uani 1 1 d . . . . .
H34 H 0.478256 0.306371 0.949991 0.052 Uiso 1 1 calc R . . . .
C35 C 0.2864(3) 0.2222(2) 0.95311(11) 0.0448(6) Uani 1 1 d . . . . .
H35 H 0.314837 0.173633 0.979610 0.054 Uiso 1 1 calc R . . . .
C36 C 0.1472(3) 0.2151(2) 0.93068(10) 0.0404(6) Uani 1 1 d . . . . .
H36 H 0.082811 0.161157 0.942524 0.048 Uiso 1 1 calc R . . . .
C37 C -0.1568(3) 0.2024(2) 0.89052(13) 0.0524(7) Uani 1 1 d . . . . .
H37A H -0.179163 0.233479 0.924618 0.079 Uiso 1 1 calc GR . . . .
H37B H -0.114806 0.131149 0.895293 0.079 Uiso 1 1 calc GR . . . .
H37C H -0.245959 0.196758 0.869939 0.079 Uiso 1 1 calc GR . . . .
C38 C -0.0143(3) 0.2235(2) 0.80668(11) 0.0466(6) Uani 1 1 d . . . . .
H38A H -0.102768 0.224751 0.785531 0.070 Uiso 1 1 calc GR . . . .
H38B H 0.017540 0.149472 0.811424 0.070 Uiso 1 1 calc GR . . . .
H38C H 0.062063 0.264133 0.789022 0.070 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
N1 C1 1.430(3) . ?
N1 C24 1.416(3) . ?
N1 C32 1.412(3) . ?
N2 C1 1.317(3) . ?
N2 C5 1.359(3) . ?
N3 C5 1.368(3) . ?
N3 C6 1.310(3) . ?
N4 C6 1.442(3) . ?
N4 C9 1.411(3) . ?
N4 C17 1.414(3) . ?
C1 C2 1.406(3) . ?
C2 C3 1.368(3) . ?
C3 C4 1.405(3) . ?
C4 C5 1.416(3) . ?
C4 C8 1.416(3) . ?
C6 C7 1.412(3) . ?
C7 C8 1.356(3) . ?
C9 C10 1.398(3) . ?
C9 C14 1.398(3) . ?
C10 C11 1.381(4) . ?
C11 C12 1.371(4) . ?
C12 C13 1.388(4) . ?
C13 C14 1.390(4) . ?
C14 C15 1.526(3) . ?
C15 C16 1.520(4) . ?
C15 C22 1.533(4) . ?
C15 C23 1.543(4) . ?
C16 C17 1.406(3) . ?
C16 C21 1.400(3) . ?
C17 C18 1.400(3) . ?
C18 C19 1.386(4) . ?
C19 C20 1.377(4) . ?
C20 C21 1.374(4) . ?
C24 C25 1.390(3) . ?
C24 C29 1.408(3) . ?
C25 C26 1.381(4) . ?
C26 C27 1.379(4) . ?
C27 C28 1.377(4) . ?
C28 C29 1.390(3) . ?
C29 C30 1.526(3) . ?
C30 C31 1.523(3) . ?
C30 C37 1.527(4) . ?
C30 C38 1.543(4) . ?
C31 C32 1.403(3) . ?
C31 C36 1.389(3) . ?
C32 C33 1.392(3) . ?
C33 C34 1.388(4) . ?
C34 C35 1.386(4) . ?
C35 C36 1.380(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
C24 N1 C1 121.17(19) . . ?
C32 N1 C1 119.33(19) . . ?
C32 N1 C24 119.17(19) . . ?
C1 N2 C5 117.42(19) . . ?
C6 N3 C5 116.85(19) . . ?
C9 N4 C6 116.28(18) . . ?
C9 N4 C17 119.94(19) . . ?
C17 N4 C6 116.98(19) . . ?
N2 C1 N1 114.6(2) . . ?
N2 C1 C2 124.5(2) . . ?
C2 C1 N1 120.9(2) . . ?
C3 C2 C1 118.4(2) . . ?
C2 C3 C4 119.2(2) . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 C8 124.0(2) . . ?
C5 C4 C8 117.9(2) . . ?
N2 C5 N3 115.02(19) . . ?
N2 C5 C4 122.3(2) . . ?
N3 C5 C4 122.7(2) . . ?
N3 C6 N4 116.8(2) . . ?
N3 C6 C7 124.7(2) . . ?
C7 C6 N4 118.4(2) . . ?
C8 C7 C6 119.1(2) . . ?
C7 C8 C4 118.7(2) . . ?
C10 C9 N4 119.1(2) . . ?
C14 C9 N4 121.0(2) . . ?
C14 C9 C10 119.9(2) . . ?
C11 C10 C9 120.6(2) . . ?
C12 C11 C10 120.0(2) . . ?
C11 C12 C13 119.7(2) . . ?
C12 C13 C14 121.7(2) . . ?
C9 C14 C15 122.1(2) . . ?
C13 C14 C9 118.1(2) . . ?
C13 C14 C15 119.7(2) . . ?
C14 C15 C22 108.1(2) . . ?
C14 C15 C23 110.1(2) . . ?
C16 C15 C14 111.0(2) . . ?
C16 C15 C22 108.1(2) . . ?
C16 C15 C23 110.4(2) . . ?
C22 C15 C23 109.1(3) . . ?
C17 C16 C15 122.1(2) . . ?
C21 C16 C15 120.8(2) . . ?
C21 C16 C17 117.0(2) . . ?
C16 C17 N4 120.9(2) . . ?
C18 C17 N4 119.0(2) . . ?
C18 C17 C16 120.1(2) . . ?
C19 C18 C17 120.5(2) . . ?
C20 C19 C18 120.1(2) . . ?
C21 C20 C19 119.2(2) . . ?
C20 C21 C16 123.0(2) . . ?
C25 C24 N1 122.2(2) . . ?
C25 C24 C29 120.0(2) . . ?
C29 C24 N1 117.7(2) . . ?
C26 C25 C24 120.4(2) . . ?
C27 C26 C25 120.2(2) . . ?
C28 C27 C26 119.4(2) . . ?
C27 C28 C29 122.1(2) . . ?
C24 C29 C30 118.7(2) . . ?
C28 C29 C24 117.7(2) . . ?
C28 C29 C30 123.4(2) . . ?
C29 C30 C37 112.1(2) . . ?
C29 C30 C38 108.1(2) . . ?
C31 C30 C29 107.8(2) . . ?
C31 C30 C37 112.7(2) . . ?
C31 C30 C38 108.0(2) . . ?
C37 C30 C38 108.0(2) . . ?
C32 C31 C30 117.9(2) . . ?
C36 C31 C30 124.2(2) . . ?
C36 C31 C32 117.8(2) . . ?
C31 C32 N1 118.9(2) . . ?
C33 C32 N1 120.6(2) . . ?
C33 C32 C31 120.4(2) . . ?
C34 C33 C32 120.2(2) . . ?
C35 C34 C33 119.9(2) . . ?
C36 C35 C34 119.5(2) . . ?
C35 C36 C31 122.1(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 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.611
####################################################################### 
# 
# 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_tx257
_database_code_depnum_ccdc_archive 'CCDC 1893133'
loop_
_audit_author_name
_audit_author_address
D-ND
;Institute of Chemistry, CAS
China
;
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-03-19 downloaded from the CCDC.
;
_audit_creation_date             2019-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_formula_moiety         'C32 H20 N4 O2'
_chemical_formula_sum            'C32 H20 N4 O2'
_chemical_formula_weight         492.52
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHN
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.84880(10)
_cell_length_b                   7.41860(10)
_cell_length_c                   16.2441(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.8480(10)
_cell_angle_gamma                90
_cell_volume                     1147.23(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16007
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      75.3840
_cell_measurement_theta_min      2.7990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21203
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.158
_diffrn_reflns_theta_min         2.814
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  60.00   0.50    1.00    --   47.20 -19.00 -90.00  174
  2  ω     31.00 126.00   0.50    1.20    --  103.25 -77.00   0.00  190
  3  ω     91.00 169.00   0.50    1.20    --  103.25  30.00 -60.00  156
  4  ω     87.00 169.00   0.50    1.20    --  103.25  61.00  30.00  164
  5  ω     84.00 169.00   0.50    1.20    --  103.25 114.00 -55.00  170
  6  ω     47.00 120.00   0.50    1.00    --   47.20 173.00  84.00  146
  7  ω     25.00 120.00   0.50    1.00    --   47.20  77.00 -30.00  190
  8  ω     28.00 116.00   0.50    1.20    --  103.25 -30.00-180.00  176
  9  ω     31.00 112.00   0.50    1.20    --  103.25-114.00-145.00  162
 10  ω     31.00 109.00   0.50    1.20    --  103.25 -94.00 -90.00  156
 11  ω     40.00 152.00   0.50    1.20    --  103.25-173.00  73.00  224
 12  ω     31.00 109.00   0.50    1.20    --  103.25 -94.00  60.00  156
 13  ω      9.00  89.00   0.50    1.00    --   47.20-114.00-145.00  160
 14  ω     32.00 120.00   0.50    1.00    --   47.20  57.00-120.00  176
 15  ω    -88.00  -2.00   0.50    1.00    --  -47.20 114.00 -55.00  172
 16  ω   -121.00 -34.00   0.50    1.00    --  -47.20 173.00  84.00  174
 17  ω   -112.00 -26.00   0.50    1.20    --  -99.00 114.00 -55.00  172
 18  ω   -112.00 -24.00   0.50    1.20    --  -99.00  30.00-120.00  176
 19  ω   -115.00 -26.00   0.50    1.20    --  -99.00  61.00 -30.00  178
 20  ω   -115.00 -26.00   0.50    1.20    --  -99.00  61.00 150.00  178
 21  ω   -120.00 -24.00   0.50    1.00    --  -47.20 -77.00 150.00  192
 22  ω   -120.00 -41.00   0.50    1.00    --  -47.20-173.00  73.00  158
 23  ω   -120.00 -71.00   0.50    1.00    --  -47.20-125.00 -30.00   98
 24  ω   -120.00 -71.00   0.50    1.00    --  -47.20-125.00 -90.00   98
 25  ω   -120.00 -71.00   0.50    1.00    --  -47.20-125.00-120.00   98
 26  ω   -120.00 -71.00   0.50    1.00    --  -47.20-125.00-180.00   98
 27  ω   -168.00 -78.00   0.50    1.20    --  -99.00-114.00-145.00  180
 28  ω   -168.00 -81.00   0.50    1.20    --  -99.00 -94.00 -30.00  174
 29  ω   -168.00 -81.00   0.50    1.20    --  -99.00 -94.00  90.00  174
 30  ω   -168.00 -86.00   0.50    1.20    --  -99.00 -30.00 120.00  164
 31  ω   -151.00 -34.00   0.50    1.20    --  -99.00 173.00  84.00  234
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0540532000
_diffrn_orient_matrix_UB_12      0.0386454000
_diffrn_orient_matrix_UB_13      0.0792311000
_diffrn_orient_matrix_UB_21      0.0374347000
_diffrn_orient_matrix_UB_22      0.2007032000
_diffrn_orient_matrix_UB_23      -0.0046719000
_diffrn_orient_matrix_UB_31      -0.1479243000
_diffrn_orient_matrix_UB_32      0.0366759000
_diffrn_orient_matrix_UB_33      -0.0576231000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                4441
_reflns_number_total             4517
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1962 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4517
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.067
_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)+(0.0524P)²+0.1591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0810
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26),
  C29(H29), C30(H30), C31(H31), C32(H32)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.59049(13) 0.42504(19) 0.98931(7) 0.0273(3) Uani 1 1 d . . . . .
O2 O 0.22914(13) 0.4276(2) 0.25457(7) 0.0296(3) Uani 1 1 d . . . . .
N1 N 0.64984(15) 0.5745(2) 0.84645(8) 0.0223(3) Uani 1 1 d . . . . .
N2 N 0.59816(15) 0.5412(2) 0.69984(9) 0.0221(3) Uani 1 1 d . . . . .
N3 N 0.52960(15) 0.5011(2) 0.55522(9) 0.0227(3) Uani 1 1 d . . . . .
N4 N 0.43883(15) 0.4496(2) 0.41012(8) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.71823(18) 0.5089(2) 0.99736(10) 0.0234(3) Uani 1 1 d . . . . .
C2 C 0.75017(18) 0.5879(2) 0.92689(10) 0.0225(3) Uani 1 1 d . . . . .
C3 C 0.87642(19) 0.6809(3) 0.93785(11) 0.0259(4) Uani 1 1 d . . . . .
H3 H 0.896402 0.741560 0.892244 0.031 Uiso 1 1 calc R . . . .
C4 C 0.9723(2) 0.6826(3) 1.01717(11) 0.0297(4) Uani 1 1 d . . . . .
H4 H 1.057739 0.741915 1.024191 0.036 Uiso 1 1 calc R . . . .
C5 C 0.9415(2) 0.5964(3) 1.08604(11) 0.0302(4) Uani 1 1 d . . . . .
H5 H 1.007249 0.595338 1.138607 0.036 Uiso 1 1 calc R . . . .
C6 C 0.8131(2) 0.5118(3) 1.07660(11) 0.0276(4) Uani 1 1 d . . . . .
H6 H 0.790806 0.457514 1.123067 0.033 Uiso 1 1 calc R . . . .
C7 C 0.48114(18) 0.4916(2) 0.92423(10) 0.0238(3) Uani 1 1 d . . . . .
C8 C 0.50706(18) 0.5682(2) 0.85155(11) 0.0223(3) Uani 1 1 d . . . . .
C9 C 0.39328(19) 0.6315(3) 0.78841(11) 0.0272(4) Uani 1 1 d . . . . .
H9 H 0.407831 0.689701 0.740689 0.033 Uiso 1 1 calc R . . . .
C10 C 0.25754(19) 0.6070(3) 0.79726(12) 0.0329(4) Uani 1 1 d . . . . .
H10 H 0.181363 0.644148 0.753854 0.039 Uiso 1 1 calc R . . . .
C11 C 0.2343(2) 0.5284(3) 0.86945(13) 0.0344(4) Uani 1 1 d . . . . .
H11 H 0.143066 0.513272 0.874476 0.041 Uiso 1 1 calc R . . . .
C12 C 0.3467(2) 0.4720(3) 0.93428(12) 0.0297(4) Uani 1 1 d . . . . .
H12 H 0.332107 0.421810 0.983768 0.036 Uiso 1 1 calc R . . . .
C13 C 0.69017(17) 0.5182(2) 0.77365(10) 0.0205(3) Uani 1 1 d . . . . .
C14 C 0.82422(17) 0.4364(3) 0.78203(10) 0.0243(4) Uani 1 1 d . . . . .
H14 H 0.887407 0.425305 0.835210 0.029 Uiso 1 1 calc R . . . .
C15 C 0.85788(17) 0.3751(3) 0.71097(11) 0.0253(4) Uani 1 1 d . . . . .
H15 H 0.945013 0.322258 0.715158 0.030 Uiso 1 1 calc R . . . .
C16 C 0.76014(17) 0.3917(3) 0.63055(11) 0.0233(3) Uani 1 1 d . . . . .
C17 C 0.63102(17) 0.4766(2) 0.62891(10) 0.0213(3) Uani 1 1 d . . . . .
C18 C 0.55013(17) 0.4316(2) 0.48500(10) 0.0226(3) Uani 1 1 d . . . . .
C19 C 0.67292(18) 0.3364(3) 0.48087(11) 0.0269(4) Uani 1 1 d . . . . .
H19 H 0.681475 0.286336 0.429965 0.032 Uiso 1 1 calc R . . . .
C20 C 0.77820(18) 0.3204(3) 0.55366(11) 0.0272(4) Uani 1 1 d . . . . .
H20 H 0.861539 0.262675 0.552562 0.033 Uiso 1 1 calc R . . . .
C21 C 0.46681(19) 0.5056(2) 0.33262(10) 0.0241(3) Uani 1 1 d . . . . .
C22 C 0.36170(18) 0.4911(2) 0.25682(11) 0.0242(3) Uani 1 1 d . . . . .
C23 C 0.3850(2) 0.5389(3) 0.17904(11) 0.0297(4) Uani 1 1 d . . . . .
H23 H 0.313413 0.527061 0.129342 0.036 Uiso 1 1 calc R . . . .
C24 C 0.5151(2) 0.6044(3) 0.17550(12) 0.0325(4) Uani 1 1 d . . . . .
H24 H 0.532718 0.632164 0.123357 0.039 Uiso 1 1 calc R . . . .
C25 C 0.6185(2) 0.6280(3) 0.25026(13) 0.0337(4) Uani 1 1 d . . . . .
H25 H 0.704909 0.676086 0.248440 0.040 Uiso 1 1 calc R . . . .
C26 C 0.5947(2) 0.5807(3) 0.32829(11) 0.0296(4) Uani 1 1 d . . . . .
H26 H 0.664867 0.599275 0.378122 0.035 Uiso 1 1 calc R . . . .
C27 C 0.29754(18) 0.4105(3) 0.40950(10) 0.0242(3) Uani 1 1 d . . . . .
C28 C 0.19652(18) 0.4046(3) 0.33154(11) 0.0259(4) Uani 1 1 d . . . . .
C29 C 0.0570(2) 0.3719(3) 0.32680(12) 0.0367(5) Uani 1 1 d . . . . .
H29 H -0.008528 0.373542 0.274150 0.044 Uiso 1 1 calc R . . . .
C30 C 0.0136(2) 0.3367(4) 0.39938(14) 0.0503(6) Uani 1 1 d . . . . .
H30 H -0.080516 0.314733 0.396268 0.060 Uiso 1 1 calc R . . . .
C31 C 0.1130(2) 0.3347(4) 0.47703(13) 0.0488(6) Uani 1 1 d . . . . .
H31 H 0.085626 0.307543 0.526310 0.059 Uiso 1 1 calc R . . . .
C32 C 0.25238(19) 0.3725(3) 0.48229(12) 0.0355(5) Uani 1 1 d . . . . .
H32 H 0.317096 0.372722 0.535230 0.043 Uiso 1 1 calc R . . . .


_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 1.379(2) . ?
O1 C7 1.392(2) . ?
O2 C22 1.380(2) . ?
O2 C28 1.379(2) . ?
N1 C2 1.425(2) . ?
N1 C8 1.430(2) . ?
N1 C13 1.404(2) . ?
N2 C13 1.316(2) . ?
N2 C17 1.361(2) . ?
N3 C17 1.360(2) . ?
N3 C18 1.314(2) . ?
N4 C18 1.420(2) . ?
N4 C21 1.418(2) . ?
N4 C27 1.419(2) . ?
C1 C2 1.392(2) . ?
C1 C6 1.383(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.389(2) . ?
C4 C5 1.388(3) . ?
C5 C6 1.385(3) . ?
C7 C8 1.391(2) . ?
C7 C12 1.383(2) . ?
C8 C9 1.392(2) . ?
C9 C10 1.393(2) . ?
C10 C11 1.380(3) . ?
C11 C12 1.382(3) . ?
C13 C14 1.427(2) . ?
C14 C15 1.358(2) . ?
C15 C16 1.416(2) . ?
C16 C17 1.413(2) . ?
C16 C20 1.409(2) . ?
C18 C19 1.417(2) . ?
C19 C20 1.363(2) . ?
C21 C22 1.395(2) . ?
C21 C26 1.396(2) . ?
C22 C23 1.387(2) . ?
C23 C24 1.386(3) . ?
C24 C25 1.381(3) . ?
C25 C26 1.392(2) . ?
C27 C28 1.396(2) . ?
C27 C32 1.395(2) . ?
C28 C29 1.378(2) . ?
C29 C30 1.378(3) . ?
C30 C31 1.384(3) . ?
C31 C32 1.382(3) . ?

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
C1 O1 C7 114.91(13) . . ?
C28 O2 C22 117.20(13) . . ?
C2 N1 C8 114.20(13) . . ?
C13 N1 C2 120.91(14) . . ?
C13 N1 C8 122.25(14) . . ?
C13 N2 C17 117.92(14) . . ?
C18 N3 C17 118.04(15) . . ?
C21 N4 C18 120.34(13) . . ?
C21 N4 C27 117.84(14) . . ?
C27 N4 C18 121.82(13) . . ?
O1 C1 C2 120.31(14) . . ?
O1 C1 C6 118.50(15) . . ?
C6 C1 C2 121.18(16) . . ?
C1 C2 N1 118.35(15) . . ?
C1 C2 C3 119.06(15) . . ?
C3 C2 N1 122.56(15) . . ?
C4 C3 C2 119.72(16) . . ?
C5 C4 C3 120.41(17) . . ?
C6 C5 C4 120.11(16) . . ?
C1 C6 C5 119.33(16) . . ?
C8 C7 O1 120.98(14) . . ?
C12 C7 O1 116.80(15) . . ?
C12 C7 C8 122.18(16) . . ?
C7 C8 N1 117.33(15) . . ?
C7 C8 C9 118.33(15) . . ?
C9 C8 N1 124.33(15) . . ?
C8 C9 C10 119.51(17) . . ?
C11 C10 C9 121.01(17) . . ?
C10 C11 C12 120.04(16) . . ?
C11 C12 C7 118.82(16) . . ?
N1 C13 C14 120.02(14) . . ?
N2 C13 N1 116.86(14) . . ?
N2 C13 C14 123.10(14) . . ?
C15 C14 C13 118.85(14) . . ?
C14 C15 C16 119.91(15) . . ?
C17 C16 C15 116.87(14) . . ?
C20 C16 C15 125.09(15) . . ?
C20 C16 C17 117.90(15) . . ?
N2 C17 C16 123.29(14) . . ?
N3 C17 N2 114.68(14) . . ?
N3 C17 C16 122.03(14) . . ?
N3 C18 N4 116.75(15) . . ?
N3 C18 C19 124.03(15) . . ?
C19 C18 N4 119.18(14) . . ?
C20 C19 C18 118.12(15) . . ?
C19 C20 C16 119.68(16) . . ?
C22 C21 N4 119.47(15) . . ?
C22 C21 C26 117.49(15) . . ?
C26 C21 N4 123.02(15) . . ?
O2 C22 C21 122.19(14) . . ?
O2 C22 C23 116.09(15) . . ?
C23 C22 C21 121.72(17) . . ?
C24 C23 C22 119.89(17) . . ?
C25 C24 C23 119.28(16) . . ?
C24 C25 C26 120.69(18) . . ?
C25 C26 C21 120.76(17) . . ?
C28 C27 N4 118.84(14) . . ?
C32 C27 N4 124.09(15) . . ?
C32 C27 C28 117.04(15) . . ?
O2 C28 C27 122.75(15) . . ?
C29 C28 O2 115.59(15) . . ?
C29 C28 C27 121.65(15) . . ?
C30 C29 C28 120.58(17) . . ?
C29 C30 C31 118.69(18) . . ?
C32 C31 C30 120.88(18) . . ?
C31 C32 C27 121.07(17) . . ?

_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 1.461
_oxdiff_exptl_absorpt_empirical_full_min 0.640
####################################################################### 
# 
# 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_tx279a_sq
_database_code_depnum_ccdc_archive 'CCDC 1893132'
loop_
_audit_author_name
_audit_author_address
D-ND
;Institute of Chemistry, CAS
China
;
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-03-19 downloaded from the CCDC.
;
_audit_creation_date             2019-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_formula_moiety         'C32 H20 N4 S2'
_chemical_formula_sum            'C32 H20 N4 S2'
_chemical_formula_weight         524.64
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   8.18250(10)
_cell_length_b                   27.5249(2)
_cell_length_c                   12.85110(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2894.36(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22136
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      75.2500
_cell_measurement_theta_min      3.2160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.869
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.7169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.311
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0092
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24727
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.577
_diffrn_reflns_theta_min         3.211
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2942
_reflns_number_total             2965
_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 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.112
_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)+(0.0498P)²+2.7974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1 S 0.15967(5) 0.44977(2) 0.39057(3) 0.02121(12) Uani 1 1 d . . . . .
N1 N 0.41079(18) 0.37605(5) 0.43213(11) 0.0204(3) Uani 1 1 d . . . . .
N2 N 0.41281(17) 0.29179(5) 0.42400(11) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.3722(2) 0.46017(6) 0.38138(12) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.4779(2) 0.42197(6) 0.40325(12) 0.0180(3) Uani 1 1 d . . . . .
C3 C 0.6460(2) 0.42952(6) 0.40104(14) 0.0216(4) Uani 1 1 d . . . . .
H3 H 0.718613 0.403883 0.418670 0.026 Uiso 1 1 calc R . . . .
C4 C 0.7071(2) 0.47480(7) 0.37287(13) 0.0227(4) Uani 1 1 d . . . . .
H4 H 0.821854 0.479858 0.369821 0.027 Uiso 1 1 calc R . . . .
C5 C 0.6015(2) 0.51258(6) 0.34923(13) 0.0212(3) Uani 1 1 d . . . . .
H5 H 0.644129 0.543269 0.329038 0.025 Uiso 1 1 calc R . . . .
C6 C 0.4337(2) 0.50576(6) 0.35495(13) 0.0200(3) Uani 1 1 d . . . . .
H6 H 0.361327 0.531948 0.340977 0.024 Uiso 1 1 calc R . . . .
C7 C 0.16311(19) 0.41143(6) 0.50114(13) 0.0188(3) Uani 1 1 d . . . . .
C8 C 0.2888(2) 0.37745(6) 0.51178(13) 0.0187(3) Uani 1 1 d . . . . .
C9 C 0.2964(2) 0.34849(6) 0.60056(13) 0.0233(4) Uani 1 1 d . . . . .
H9 H 0.383600 0.326095 0.609477 0.028 Uiso 1 1 calc R . . . .
C10 C 0.1753(2) 0.35260(7) 0.67611(15) 0.0290(4) Uani 1 1 d . . . . .
H10 H 0.179152 0.332585 0.736288 0.035 Uiso 1 1 calc R . . . .
C11 C 0.0488(2) 0.38579(7) 0.66402(15) 0.0307(4) Uani 1 1 d . . . . .
H11 H -0.034336 0.387985 0.715436 0.037 Uiso 1 1 calc R . . . .
C12 C 0.0431(2) 0.41568(7) 0.57747(15) 0.0261(4) Uani 1 1 d . . . . .
H12 H -0.041951 0.438916 0.570185 0.031 Uiso 1 1 calc R . . . .
C13 C 0.4537(2) 0.33342(6) 0.37975(13) 0.0191(3) Uani 1 1 d . . . . .
C14 C 0.4529(3) 0.250000 0.37336(19) 0.0191(5) Uani 1 2 d S T P . .
C15 C 0.5319(3) 0.250000 0.2755(2) 0.0237(5) Uani 1 2 d S T P . .
C16 C 0.5686(2) 0.20462(6) 0.22975(15) 0.0282(4) Uani 1 1 d . . . . .
H16 H 0.619091 0.203301 0.163235 0.034 Uiso 1 1 calc R . . . .
C17 C 0.5317(2) 0.16287(6) 0.28104(14) 0.0255(4) Uani 1 1 d . . . . .
H17 H 0.557137 0.132076 0.251844 0.031 Uiso 1 1 calc R . . . .


_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
S1 C1 1.7663(17) . ?
S1 C7 1.7702(17) . ?
N1 C2 1.427(2) . ?
N1 C8 1.430(2) . ?
N1 C13 1.397(2) . ?
N2 C13 1.322(2) . ?
N2 C14 1.3617(19) . ?
C1 C2 1.390(2) . ?
C1 C6 1.394(2) . ?
C2 C3 1.391(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(2) . ?
C7 C12 1.393(2) . ?
C8 C9 1.393(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C17 1.424(2) 7_565 ?
C14 C15 1.414(3) . ?
C15 C16 1.413(2) 7_565 ?
C15 C16 1.413(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.359(3) . ?
C17 H17 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
C1 S1 C7 97.74(8) . . ?
C2 N1 C8 115.51(13) . . ?
C13 N1 C2 121.45(14) . . ?
C13 N1 C8 122.87(13) . . ?
C13 N2 C14 117.75(15) . . ?
C2 C1 S1 118.46(13) . . ?
C2 C1 C6 120.36(15) . . ?
C6 C1 S1 121.17(13) . . ?
C1 C2 N1 118.88(15) . . ?
C1 C2 C3 119.87(15) . . ?
C3 C2 N1 121.19(15) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.64(16) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.35(16) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.25(16) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.46(16) . . ?
C5 C6 H6 120.3 . . ?
C8 C7 S1 119.30(12) . . ?
C12 C7 S1 120.27(13) . . ?
C12 C7 C8 120.42(16) . . ?
C7 C8 N1 117.51(15) . . ?
C9 C8 N1 122.66(15) . . ?
C9 C8 C7 119.73(15) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.55(17) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.39(17) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.36(17) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 120.2 . . ?
C11 C12 C7 119.51(17) . . ?
C11 C12 H12 120.2 . . ?
N1 C13 C17 118.79(15) . 7_565 ?
N2 C13 N1 117.19(15) . . ?
N2 C13 C17 123.97(15) . 7_565 ?
N2 C14 N2 115.3(2) . 7_565 ?
N2 C14 C15 122.35(10) . . ?
N2 C14 C15 122.35(10) 7_565 . ?
C16 C15 C14 117.86(11) . . ?
C16 C15 C14 117.86(11) 7_565 . ?
C16 C15 C16 124.3(2) . 7_565 ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.90(17) . . ?
C17 C16 H16 120.0 . . ?
C13 C17 H17 120.9 7_565 . ?
C16 C17 C13 118.12(16) . 7_565 ?
C16 C17 H17 120.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
