# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_zhx-4054
_database_code_depnum_ccdc_archive 'CCDC 2041453'
loop_
_audit_author_name
_audit_author_address
'zhang huaxing'
;sichuan university
China
;
_audit_update_record             
;
2020-10-30 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H18 N2'
_chemical_formula_sum            'C31 H18 N2'
_chemical_formula_weight         418.47
_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'

_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                   8.2871(4)
_cell_length_b                   9.5533(5)
_cell_length_c                   14.9700(8)
_cell_angle_alpha                73.340(5)
_cell_angle_beta                 87.044(4)
_cell_angle_gamma                72.220(5)
_cell_volume                     1080.34(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3706
_cell_measurement_temperature    292.8(8)
_cell_measurement_theta_max      71.2530
_cell_measurement_theta_min      5.0630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9414
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.544
_diffrn_reflns_theta_min         5.072
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.8(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -13.00   1.00    1.82    --  -35.23 -38.00  30.00   93
  2  ω    -57.00  35.00   1.00    1.82    --  -35.23  38.00-150.00   92
  3  ω     23.00  90.00   1.00    1.82    --   35.23-125.00-120.00   67
  4  ω     17.00 104.00   1.00    1.82    --   35.23  57.00   0.00   87
  5  ω    -34.00  64.00   1.00    1.82    --   35.23 -77.00  90.00   98
  6  ω     17.00 104.00   1.00    1.82    --   35.23  57.00-120.00   87
  7  ω     23.00  90.00   1.00    1.82    --   35.23-125.00  30.00   67
  8  ω     17.00 104.00   1.00    1.82    --   35.23  57.00 -60.00   87
  9  ω     36.00 113.00   1.00    7.28    --  106.90-111.00-150.00   77
 10  ω     61.00 178.00   1.00    7.28    --  106.90  15.00-180.00  117
 11  ω     81.00 178.00   1.00    7.28    --  106.90  30.00  60.00   97
 12  ω     87.00 177.00   1.00    7.28    --  106.90  45.00 -30.00   90
 13  ω    100.00 178.00   1.00    7.28    --  106.90 111.00-120.00   78
 14  ω     37.00 127.00   1.00    7.28    --  106.90 -45.00-120.00   90
 15  ω     35.00 133.00   1.00    7.28    --  106.90 -30.00 150.00   98
 16  ω     37.00 110.00   1.00    7.28    --  106.90 -94.00 -90.00   73
 17  ω     37.00 110.00   1.00    7.28    --  106.90 -94.00  60.00   73
 18  ω     37.00 110.00   1.00    7.28    --  106.90 -94.00   0.00   73
 19  ω     61.00 178.00   1.00    7.28    --  106.90  15.00-180.00  117
 20  ω     37.00 127.00   1.00    7.28    --  106.90 -45.00 -30.00   90
 21  ω     37.00 110.00   1.00    7.28    --  106.90 -94.00-120.00   73
 22  ω     17.00 104.00   1.00    1.82    --   35.23  57.00 150.00   87
 23  ω    -33.00 -21.00   1.00    1.82    --   35.23 -57.00   0.00   12
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1149156000
_diffrn_orient_matrix_UB_12      -0.0951843000
_diffrn_orient_matrix_UB_13      -0.0594421000
_diffrn_orient_matrix_UB_21      0.0135054000
_diffrn_orient_matrix_UB_22      -0.1480197000
_diffrn_orient_matrix_UB_23      0.0791916000
_diffrn_orient_matrix_UB_31      -0.1574270000
_diffrn_orient_matrix_UB_32      -0.0155885000
_diffrn_orient_matrix_UB_33      -0.0418590000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3359
_reflns_number_total             4092
_reflns_odcompleteness_completeness 99.30
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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         0.212
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.032
_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)+(0.1315P)²+0.0284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.1916
_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:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I), C00K(H00K),
 C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X)
;
_atom_sites_solution_hydrogens   geom
_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
N001 N 0.81962(18) 0.30120(16) 0.61116(10) 0.0488(4) Uani 1 1 d . . . . .
N002 N 0.7384(2) 0.56351(19) 0.45204(10) 0.0558(4) Uani 1 1 d . . . . .
C003 C 0.8060(2) 0.26418(18) 0.82793(10) 0.0440(4) Uani 1 1 d . . . . .
C004 C 0.6057(2) 0.16572(18) 0.78186(10) 0.0437(4) Uani 1 1 d . . . . .
C005 C 0.6017(2) 0.43936(18) 0.69208(11) 0.0436(4) Uani 1 1 d . . . . .
C006 C 0.6962(2) 0.42977(18) 0.61104(11) 0.0444(4) Uani 1 1 d . . . . .
C007 C 0.8753(2) 0.10539(19) 0.84875(11) 0.0477(4) Uani 1 1 d . . . . .
C008 C 0.7487(2) 0.04397(19) 0.82142(11) 0.0479(4) Uani 1 1 d . . . . .
C009 C 0.6276(2) 0.31727(17) 0.78508(10) 0.0427(4) Uani 1 1 d . . . . .
C00A C 0.4047(2) 0.54693(18) 0.78699(12) 0.0458(4) Uani 1 1 d . . . . .
C00B C 0.49391(19) 0.40015(18) 0.84198(11) 0.0437(4) Uani 1 1 d . . . . .
C00C C 0.4750(2) 0.56960(18) 0.69370(12) 0.0466(4) Uani 1 1 d . . . . .
C00D C 0.8979(2) 0.3531(2) 0.84482(12) 0.0526(4) Uani 1 1 d . . . . .
H00D H 0.8508 0.4590 0.8312 0.063 Uiso 1 1 calc R . . . .
C00E C 0.4688(2) 0.1420(2) 0.74695(12) 0.0526(4) Uani 1 1 d . . . . .
H00E H 0.3747 0.2239 0.7196 0.063 Uiso 1 1 calc R . . . .
C00F C 0.4586(2) 0.3490(2) 0.93448(11) 0.0488(4) Uani 1 1 d . . . . .
H00F H 0.5185 0.2515 0.9709 0.059 Uiso 1 1 calc R . . . .
C00G C 0.4312(2) 0.7003(2) 0.61357(13) 0.0539(4) Uani 1 1 d . . . . .
H00G H 0.3436 0.7876 0.6154 0.065 Uiso 1 1 calc R . . . .
C00H C 0.6536(2) 0.5627(2) 0.53050(11) 0.0491(4) Uani 1 1 d . . . . .
C00I C 0.2765(2) 0.6430(2) 0.82520(13) 0.0548(4) Uani 1 1 d . . . . .
H00I H 0.2154 0.7403 0.7891 0.066 Uiso 1 1 calc R . . . .
C00J C 0.9036(2) 0.3026(2) 0.53160(12) 0.0526(4) Uani 1 1 d . . . . .
C00K C 1.0392(2) 0.0349(2) 0.88613(14) 0.0624(5) Uani 1 1 d . . . . .
H00K H 1.0867 -0.0709 0.9000 0.075 Uiso 1 1 calc R . . . .
C00L C 0.3317(2) 0.4462(2) 0.97220(12) 0.0542(4) Uani 1 1 d . . . . .
H00L H 0.3069 0.4135 1.0346 0.065 Uiso 1 1 calc R . . . .
C00M C 0.2422(2) 0.5902(2) 0.91838(14) 0.0588(5) Uani 1 1 d . . . . .
H00M H 0.1573 0.6532 0.9449 0.071 Uiso 1 1 calc R . . . .
C00N C 0.8626(2) 0.4349(2) 0.45202(12) 0.0544(4) Uani 1 1 d . . . . .
C00O C 0.5187(3) 0.6957(2) 0.53470(13) 0.0570(4) Uani 1 1 d . . . . .
H00O H 0.4903 0.7808 0.4825 0.068 Uiso 1 1 calc R . . . .
C00P C 0.7527(3) -0.1050(2) 0.82832(15) 0.0633(5) Uani 1 1 d . . . . .
H00P H 0.8467 -0.1872 0.8555 0.076 Uiso 1 1 calc R . . . .
C00Q C 0.4755(3) -0.0081(2) 0.75388(15) 0.0627(5) Uani 1 1 d . . . . .
H00Q H 0.3844 -0.0267 0.7309 0.075 Uiso 1 1 calc R . . . .
C00R C 1.1312(2) 0.1248(3) 0.90253(15) 0.0678(5) Uani 1 1 d . . . . .
H00R H 1.2416 0.0786 0.9275 0.081 Uiso 1 1 calc R . . . .
C00S C 1.0615(3) 0.2814(3) 0.88247(14) 0.0630(5) Uani 1 1 d . . . . .
H00S H 1.1251 0.3397 0.8943 0.076 Uiso 1 1 calc R . . . .
C00T C 0.6145(3) -0.1291(2) 0.79415(17) 0.0680(5) Uani 1 1 d . . . . .
H00T H 0.6158 -0.2286 0.7985 0.082 Uiso 1 1 calc R . . . .
C00U C 0.9562(3) 0.4282(3) 0.37025(14) 0.0692(6) Uani 1 1 d . . . . .
H00U H 0.9326 0.5135 0.3181 0.083 Uiso 1 1 calc R . . . .
C00V C 1.0344(3) 0.1696(3) 0.52612(16) 0.0683(5) Uani 1 1 d . . . . .
H00V H 1.0625 0.0832 0.5776 0.082 Uiso 1 1 calc R . . . .
C00W C 1.0792(3) 0.2987(3) 0.36792(17) 0.0817(7) Uani 1 1 d . . . . .
H00W H 1.1389 0.2957 0.3138 0.098 Uiso 1 1 calc R . . . .
C00X C 1.1190(3) 0.1676(3) 0.4460(2) 0.0808(7) Uani 1 1 d . . . . .
H00X H 1.2037 0.0793 0.4427 0.097 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
N001 C006 1.336(2) . ?
N001 C00J 1.347(2) . ?
N002 C00H 1.336(2) . ?
N002 C00N 1.341(3) . ?
C003 C007 1.394(2) . ?
C003 C009 1.519(2) . ?
C003 C00D 1.380(2) . ?
C004 C008 1.394(2) . ?
C004 C009 1.527(2) . ?
C004 C00E 1.377(2) . ?
C005 C006 1.420(2) . ?
C005 C009 1.514(2) . ?
C005 C00C 1.367(2) . ?
C006 C00H 1.443(2) . ?
C007 C008 1.474(2) . ?
C007 C00K 1.384(3) . ?
C008 C00P 1.387(2) . ?
C009 C00B 1.528(2) . ?
C00A C00B 1.399(2) . ?
C00A C00C 1.468(2) . ?
C00A C00I 1.393(2) . ?
C00B C00F 1.378(2) . ?
C00C C00G 1.428(2) . ?
C00D H00D 0.9300 . ?
C00D C00S 1.385(3) . ?
C00E H00E 0.9300 . ?
C00E C00Q 1.392(3) . ?
C00F H00F 0.9300 . ?
C00F C00L 1.389(2) . ?
C00G H00G 0.9300 . ?
C00G C00O 1.358(3) . ?
C00H C00O 1.428(3) . ?
C00I H00I 0.9300 . ?
C00I C00M 1.387(3) . ?
C00J C00N 1.431(3) . ?
C00J C00V 1.416(3) . ?
C00K H00K 0.9300 . ?
C00K C00R 1.385(3) . ?
C00L H00L 0.9300 . ?
C00L C00M 1.377(3) . ?
C00M H00M 0.9300 . ?
C00N C00U 1.421(3) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00P C00T 1.384(3) . ?
C00Q H00Q 0.9300 . ?
C00Q C00T 1.373(3) . ?
C00R H00R 0.9300 . ?
C00R C00S 1.377(3) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00U C00W 1.350(4) . ?
C00V H00V 0.9300 . ?
C00V C00X 1.360(3) . ?
C00W H00W 0.9300 . ?
C00W C00X 1.411(4) . ?
C00X H00X 0.9300 . ?

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
C006 N001 C00J 116.12(16) . . ?
C00H N002 C00N 116.68(16) . . ?
C007 C003 C009 111.12(14) . . ?
C00D C003 C007 121.01(16) . . ?
C00D C003 C009 127.85(15) . . ?
C008 C004 C009 110.43(14) . . ?
C00E C004 C008 121.39(15) . . ?
C00E C004 C009 128.18(15) . . ?
C006 C005 C009 126.80(14) . . ?
C00C C005 C006 121.22(15) . . ?
C00C C005 C009 111.95(14) . . ?
N001 C006 C005 120.12(15) . . ?
N001 C006 C00H 122.36(15) . . ?
C005 C006 C00H 117.52(15) . . ?
C003 C007 C008 108.14(14) . . ?
C00K C007 C003 119.96(17) . . ?
C00K C007 C008 131.87(16) . . ?
C004 C008 C007 108.83(14) . . ?
C00P C008 C004 119.80(17) . . ?
C00P C008 C007 131.37(17) . . ?
C003 C009 C004 101.42(12) . . ?
C003 C009 C00B 113.20(12) . . ?
C004 C009 C00B 112.96(12) . . ?
C005 C009 C003 114.08(13) . . ?
C005 C009 C004 115.00(12) . . ?
C005 C009 C00B 100.78(13) . . ?
C00B C00A C00C 108.13(14) . . ?
C00I C00A C00B 120.05(16) . . ?
C00I C00A C00C 131.81(16) . . ?
C00A C00B C009 110.40(14) . . ?
C00F C00B C009 128.63(15) . . ?
C00F C00B C00A 120.96(15) . . ?
C005 C00C C00A 108.73(14) . . ?
C005 C00C C00G 121.24(16) . . ?
C00G C00C C00A 130.02(15) . . ?
C003 C00D H00D 120.7 . . ?
C003 C00D C00S 118.56(18) . . ?
C00S C00D H00D 120.7 . . ?
C004 C00E H00E 121.0 . . ?
C004 C00E C00Q 118.02(17) . . ?
C00Q C00E H00E 121.0 . . ?
C00B C00F H00F 120.7 . . ?
C00B C00F C00L 118.58(16) . . ?
C00L C00F H00F 120.7 . . ?
C00C C00G H00G 120.3 . . ?
C00O C00G C00C 119.33(17) . . ?
C00O C00G H00G 120.3 . . ?
N002 C00H C006 121.12(17) . . ?
N002 C00H C00O 119.41(16) . . ?
C00O C00H C006 119.47(15) . . ?
C00A C00I H00I 120.8 . . ?
C00M C00I C00A 118.43(17) . . ?
C00M C00I H00I 120.8 . . ?
N001 C00J C00N 121.58(17) . . ?
N001 C00J C00V 119.29(18) . . ?
C00V C00J C00N 119.13(17) . . ?
C007 C00K H00K 120.6 . . ?
C007 C00K C00R 118.81(19) . . ?
C00R C00K H00K 120.6 . . ?
C00F C00L H00L 119.6 . . ?
C00M C00L C00F 120.85(17) . . ?
C00M C00L H00L 119.6 . . ?
C00I C00M H00M 119.4 . . ?
C00L C00M C00I 121.12(16) . . ?
C00L C00M H00M 119.4 . . ?
N002 C00N C00J 122.14(16) . . ?
N002 C00N C00U 119.28(19) . . ?
C00U C00N C00J 118.6(2) . . ?
C00G C00O C00H 121.21(16) . . ?
C00G C00O H00O 119.4 . . ?
C00H C00O H00O 119.4 . . ?
C008 C00P H00P 120.6 . . ?
C00T C00P C008 118.88(19) . . ?
C00T C00P H00P 120.6 . . ?
C00E C00Q H00Q 119.5 . . ?
C00T C00Q C00E 121.08(18) . . ?
C00T C00Q H00Q 119.5 . . ?
C00K C00R H00R 119.5 . . ?
C00S C00R C00K 120.95(19) . . ?
C00S C00R H00R 119.5 . . ?
C00D C00S H00S 119.6 . . ?
C00R C00S C00D 120.71(18) . . ?
C00R C00S H00S 119.6 . . ?
C00P C00T H00T 119.6 . . ?
C00Q C00T C00P 120.81(18) . . ?
C00Q C00T H00T 119.6 . . ?
C00N C00U H00U 119.9 . . ?
C00W C00U C00N 120.3(2) . . ?
C00W C00U H00U 119.9 . . ?
C00J C00V H00V 119.8 . . ?
C00X C00V C00J 120.3(2) . . ?
C00X C00V H00V 119.8 . . ?
C00U C00W H00W 119.4 . . ?
C00U C00W C00X 121.3(2) . . ?
C00X C00W H00W 119.4 . . ?
C00V C00X C00W 120.4(2) . . ?
C00V C00X H00X 119.8 . . ?
C00W C00X H00X 119.8 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-10-12
_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 1.831
_oxdiff_exptl_absorpt_empirical_full_min 0.725
####################################################################### 
# 
# 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_zhx-4148
_database_code_depnum_ccdc_archive 'CCDC 2071049'
loop_
_audit_author_name
_audit_author_address
'zhang huaxing'
;sichuan university
China
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-11-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H15 F2 N3'
_chemical_formula_sum            'C24 H15 F2 N3'
_chemical_formula_weight         383.39
_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'
F F 0.0727 0.0534 '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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   7.16800(11)
_cell_length_b                   22.8606(4)
_cell_length_c                   23.0265(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3773.23(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3512
_cell_measurement_temperature    296.75(10)
_cell_measurement_theta_max      71.5760
_cell_measurement_theta_min      3.8350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11013
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.446
_diffrn_reflns_theta_min         3.839
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.75(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -19.00   1.00    1.90    --  -36.17 -57.00 -30.00   84
  2  ω     23.00  90.00   1.00    1.90    --   36.17-125.00 120.00   67
  3  ω      7.00 108.00   1.00    1.90    --   36.17  19.00 120.00  101
  4  ω    100.00 176.00   1.00    7.60    --  106.21 111.00 -30.00   76
  5  ω    100.00 176.00   1.00    7.60    --  106.21 111.00 120.00   76
  6  ω     36.00 113.00   1.00    7.60    --  106.21-111.00 120.00   77
  7  ω     38.00 124.00   1.00    7.60    --  106.21 -45.00-150.00   86
  8  ω     37.00 109.00   1.00    7.60    --  106.21 -94.00-180.00   72
  9  ω   -105.00 -79.00   1.00    1.90    --  -36.17 -38.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0366230000
_diffrn_orient_matrix_UB_12      -0.0664007000
_diffrn_orient_matrix_UB_13      -0.0006136000
_diffrn_orient_matrix_UB_21      -0.0667831000
_diffrn_orient_matrix_UB_22      -0.0041836000
_diffrn_orient_matrix_UB_23      0.0634426000
_diffrn_orient_matrix_UB_31      -0.2010395000
_diffrn_orient_matrix_UB_32      -0.0106939000
_diffrn_orient_matrix_UB_33      -0.0211810000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2970
_reflns_number_total             3607
_reflns_odcompleteness_completeness 99.87
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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         0.330
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.102
_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     262
_refine_ls_number_reflns         3607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0662
_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)+(0.1163P)²+0.4030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1818
_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:
 C009(H009), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T)
;
_atom_sites_solution_hydrogens   geom
_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
F001 F 0.4536(2) 0.33820(6) 0.07638(7) 0.0721(4) Uani 1 1 d . . . . .
F002 F 0.3882(3) 0.43667(7) 0.01866(6) 0.0805(5) Uani 1 1 d . . . . .
N003 N 0.2951(2) 0.53999(6) 0.19418(7) 0.0422(4) Uani 1 1 d . . . . .
N004 N 0.2636(2) 0.64311(7) 0.37581(7) 0.0451(4) Uani 1 1 d . . . . .
N005 N 0.3691(2) 0.43468(6) 0.25584(7) 0.0416(4) Uani 1 1 d . . . . .
C006 C 0.1670(3) 0.69188(7) 0.35150(8) 0.0415(4) Uani 1 1 d . . . . .
C007 C 0.2981(2) 0.53834(7) 0.25248(8) 0.0379(4) Uani 1 1 d . . . . .
C008 C 0.3361(2) 0.48494(7) 0.28351(8) 0.0382(4) Uani 1 1 d . . . . .
C009 C 0.2720(2) 0.59091(7) 0.28398(8) 0.0407(4) Uani 1 1 d . . . . .
H009 H 0.2467 0.6254 0.2641 0.049 Uiso 1 1 calc R . . . .
C00A C 0.2834(2) 0.59149(7) 0.34318(8) 0.0401(4) Uani 1 1 d . . . . .
C00B C 0.3684(2) 0.43648(8) 0.19758(8) 0.0400(4) Uani 1 1 d . . . . .
C00C C 0.3323(2) 0.48945(8) 0.16644(8) 0.0412(4) Uani 1 1 d . . . . .
C00D C 0.3904(3) 0.65322(8) 0.42253(8) 0.0442(4) Uani 1 1 d . . . . .
C00E C 0.2514(3) 0.74633(8) 0.34794(9) 0.0491(5) Uani 1 1 d . . . . .
H00E H 0.3730 0.7514 0.3611 0.059 Uiso 1 1 calc R . . . .
C00F C -0.0141(3) 0.68501(9) 0.33204(9) 0.0511(5) Uani 1 1 d . . . . .
H00F H -0.0723 0.6488 0.3348 0.061 Uiso 1 1 calc R . . . .
C00G C 0.3401(3) 0.48684(8) 0.34511(8) 0.0440(4) Uani 1 1 d . . . . .
H00G H 0.3602 0.4526 0.3659 0.053 Uiso 1 1 calc R . . . .
C00H C 0.4089(3) 0.38457(8) 0.16594(9) 0.0477(5) Uani 1 1 d . . . . .
H00H H 0.4323 0.3497 0.1854 0.057 Uiso 1 1 calc R . . . .
C00I C 0.3150(3) 0.53785(8) 0.37398(8) 0.0437(4) Uani 1 1 d . . . . .
H00I H 0.3183 0.5381 0.4144 0.052 Uiso 1 1 calc R . . . .
C00J C 0.1543(3) 0.79322(9) 0.32470(10) 0.0549(5) Uani 1 1 d . . . . .
H00J H 0.2111 0.8297 0.3226 0.066 Uiso 1 1 calc R . . . .
C00K C 0.3368(3) 0.48894(9) 0.10468(9) 0.0517(5) Uani 1 1 d . . . . .
H00K H 0.3117 0.5228 0.0838 0.062 Uiso 1 1 calc R . . . .
C00L C 0.5754(3) 0.63600(10) 0.41859(10) 0.0566(5) Uani 1 1 d . . . . .
H00L H 0.6186 0.6176 0.3852 0.068 Uiso 1 1 calc R . . . .
C00M C 0.3279(3) 0.68111(9) 0.47212(9) 0.0546(5) Uani 1 1 d . . . . .
H00M H 0.2041 0.6930 0.4749 0.066 Uiso 1 1 calc R . . . .
C00N C 0.4131(3) 0.38638(9) 0.10778(9) 0.0516(5) Uani 1 1 d . . . . .
C00O C -0.0242(3) 0.78635(10) 0.30489(10) 0.0589(5) Uani 1 1 d . . . . .
H00O H -0.0883 0.8180 0.2892 0.071 Uiso 1 1 calc R . . . .
C00P C 0.3781(3) 0.43861(10) 0.07678(9) 0.0547(5) Uani 1 1 d . . . . .
C00Q C -0.1090(3) 0.73221(10) 0.30833(11) 0.0604(6) Uani 1 1 d . . . . .
H00Q H -0.2301 0.7274 0.2947 0.073 Uiso 1 1 calc R . . . .
C00R C 0.4487(4) 0.69130(12) 0.51742(11) 0.0696(7) Uani 1 1 d . . . . .
H00R H 0.4067 0.7104 0.5506 0.084 Uiso 1 1 calc R . . . .
C00S C 0.6952(3) 0.64620(12) 0.46442(13) 0.0725(7) Uani 1 1 d . . . . .
H00S H 0.8193 0.6346 0.4618 0.087 Uiso 1 1 calc R . . . .
C00T C 0.6321(4) 0.67330(12) 0.51380(12) 0.0757(7) Uani 1 1 d . . . . .
H00T H 0.7128 0.6795 0.5448 0.091 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
F001 C00N 1.349(2) . ?
F002 C00P 1.341(2) . ?
N003 C007 1.343(2) . ?
N003 C00C 1.347(2) . ?
N004 C006 1.427(2) . ?
N004 C00A 1.406(2) . ?
N004 C00D 1.427(2) . ?
N005 C008 1.335(2) . ?
N005 C00B 1.342(2) . ?
C006 C00E 1.386(3) . ?
C006 C00F 1.382(3) . ?
C007 C008 1.440(2) . ?
C007 C009 1.416(2) . ?
C008 C00G 1.419(3) . ?
C009 H009 0.9300 . ?
C009 C00A 1.366(3) . ?
C00A C00I 1.435(3) . ?
C00B C00C 1.431(3) . ?
C00B C00H 1.422(2) . ?
C00C C00K 1.423(3) . ?
C00D C00L 1.386(3) . ?
C00D C00M 1.383(3) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.386(3) . ?
C00F H00F 0.9300 . ?
C00F C00Q 1.387(3) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.354(3) . ?
C00H H00H 0.9300 . ?
C00H C00N 1.340(3) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00O 1.368(3) . ?
C00K H00K 0.9300 . ?
C00K C00P 1.350(3) . ?
C00L H00L 0.9300 . ?
C00L C00S 1.380(3) . ?
C00M H00M 0.9300 . ?
C00M C00R 1.376(3) . ?
C00N C00P 1.413(3) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.381(3) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00T 1.380(4) . ?
C00S H00S 0.9300 . ?
C00S C00T 1.372(4) . ?
C00T H00T 0.9300 . ?

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
C007 N003 C00C 116.54(15) . . ?
C006 N004 C00D 118.57(15) . . ?
C00A N004 C006 119.68(15) . . ?
C00A N004 C00D 118.30(15) . . ?
C008 N005 C00B 116.73(15) . . ?
C00E C006 N004 120.88(17) . . ?
C00F C006 N004 119.62(16) . . ?
C00F C006 C00E 119.50(18) . . ?
N003 C007 C008 121.51(15) . . ?
N003 C007 C009 119.08(15) . . ?
C009 C007 C008 119.35(16) . . ?
N005 C008 C007 121.75(16) . . ?
N005 C008 C00G 119.97(16) . . ?
C00G C008 C007 118.27(15) . . ?
C007 C009 H009 119.6 . . ?
C00A C009 C007 120.76(16) . . ?
C00A C009 H009 119.6 . . ?
N004 C00A C00I 117.98(16) . . ?
C009 C00A N004 122.37(16) . . ?
C009 C00A C00I 119.65(16) . . ?
N005 C00B C00C 121.85(15) . . ?
N005 C00B C00H 119.04(16) . . ?
C00H C00B C00C 119.09(18) . . ?
N003 C00C C00B 121.61(17) . . ?
N003 C00C C00K 119.06(17) . . ?
C00K C00C C00B 119.33(16) . . ?
C00L C00D N004 120.93(18) . . ?
C00M C00D N004 119.38(18) . . ?
C00M C00D C00L 119.69(19) . . ?
C006 C00E H00E 120.1 . . ?
C00J C00E C006 119.89(19) . . ?
C00J C00E H00E 120.1 . . ?
C006 C00F H00F 120.0 . . ?
C006 C00F C00Q 119.99(19) . . ?
C00Q C00F H00F 120.0 . . ?
C008 C00G H00G 119.5 . . ?
C00I C00G C008 120.94(16) . . ?
C00I C00G H00G 119.5 . . ?
C00B C00H H00H 120.3 . . ?
C00N C00H C00B 119.38(18) . . ?
C00N C00H H00H 120.3 . . ?
C00A C00I H00I 119.5 . . ?
C00G C00I C00A 120.95(17) . . ?
C00G C00I H00I 119.5 . . ?
C00E C00J H00J 119.7 . . ?
C00O C00J C00E 120.66(19) . . ?
C00O C00J H00J 119.7 . . ?
C00C C00K H00K 120.4 . . ?
C00P C00K C00C 119.18(19) . . ?
C00P C00K H00K 120.4 . . ?
C00D C00L H00L 120.1 . . ?
C00S C00L C00D 119.8(2) . . ?
C00S C00L H00L 120.1 . . ?
C00D C00M H00M 120.0 . . ?
C00R C00M C00D 120.0(2) . . ?
C00R C00M H00M 120.0 . . ?
F001 C00N C00P 117.21(19) . . ?
C00H C00N F001 121.00(19) . . ?
C00H C00N C00P 121.79(18) . . ?
C00J C00O H00O 120.2 . . ?
C00J C00O C00Q 119.7(2) . . ?
C00Q C00O H00O 120.2 . . ?
F002 C00P C00K 121.0(2) . . ?
F002 C00P C00N 117.80(18) . . ?
C00K C00P C00N 121.2(2) . . ?
C00F C00Q H00Q 119.9 . . ?
C00O C00Q C00F 120.3(2) . . ?
C00O C00Q H00Q 119.9 . . ?
C00M C00R H00R 119.9 . . ?
C00M C00R C00T 120.2(2) . . ?
C00T C00R H00R 119.9 . . ?
C00L C00S H00S 119.8 . . ?
C00T C00S C00L 120.3(2) . . ?
C00T C00S H00S 119.8 . . ?
C00R C00T H00T 120.0 . . ?
C00S C00T C00R 119.9(2) . . ?
C00S C00T H00T 120.0 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-11-03
_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 1.617
_oxdiff_exptl_absorpt_empirical_full_min 0.723
####################################################################### 
# 
# 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_yjs-zhx-41-3
_database_code_depnum_ccdc_archive 'CCDC 2041804'
loop_
_audit_author_name
_audit_author_address
'zhang huaxing'
;sichuan university
China
;
_audit_update_record             
;
2020-11-01 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_audit_creation_date             2019-06-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H15 N3 S'
_chemical_formula_sum            'C24 H15 N3 S'
_chemical_formula_weight         377.45
_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      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                   10.2292(3)
_cell_length_b                   16.3951(5)
_cell_length_c                   11.6492(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.281(4)
_cell_angle_gamma                90
_cell_volume                     1794.60(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3413
_cell_measurement_temperature    295.7(2)
_cell_measurement_theta_max      71.3450
_cell_measurement_theta_min      4.9010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8706
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.561
_diffrn_reflns_theta_min         4.706
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.7(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.986
_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   -105.00 -17.00   1.00    2.37    --  -36.29 -38.00  90.00   88
  2  ω   -105.00 -17.00   1.00    2.37    --  -36.29 -38.00 -30.00   88
  3  ω      1.00  75.00   1.00    2.37    --   36.29 -99.00 -60.00   74
  4  ω      1.00  75.00   1.00    2.37    --   36.29 -99.00-180.00   74
  5  ω     17.00 105.00   1.00    2.37    --   36.29  38.00 -60.00   88
  6  ω     37.00 109.00   1.00    9.50    --  106.21 -94.00   0.00   72
  7  ω     36.00 128.00   1.00    9.50    --  106.21 -30.00  30.00   92
  8  ω     89.00 175.00   1.00    9.50    --  106.21  45.00 120.00   86
  9  ω     37.00 109.00   1.00    9.50    --  106.21 -94.00 120.00   72
 10  ω     89.00 175.00   1.00    9.50    --  106.21  45.00-150.00   86
 11  ω     37.00 109.00   1.00    9.50    --  106.21 -94.00-120.00   72
 12  ω     79.00 174.00   1.00    9.50    --  106.21  77.00 -30.00   95
 13  ω     38.00  88.00   1.00    9.50    --  106.21 -45.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1604923000
_diffrn_orient_matrix_UB_12      0.0183038000
_diffrn_orient_matrix_UB_13      0.0631776000
_diffrn_orient_matrix_UB_21      -0.0315162000
_diffrn_orient_matrix_UB_22      0.0920971000
_diffrn_orient_matrix_UB_23      -0.0176709000
_diffrn_orient_matrix_UB_31      -0.0106826000
_diffrn_orient_matrix_UB_32      0.0036389000
_diffrn_orient_matrix_UB_33      0.1281880000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2957
_reflns_number_total             3377
_reflns_odcompleteness_completeness 98.77
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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         0.266
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.080
_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     253
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0628
_refine_ls_restrained_S_all      1.035
_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)+(0.1243P)²+0.2338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1770
_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:
 C00A(H00A), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S)
;
_atom_sites_solution_hydrogens   geom
_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
S001 S 0.30172(6) 0.58798(4) -0.08245(5) 0.0579(2) Uani 1 1 d . . . . .
N002 N 0.43826(16) 0.68182(11) 0.15059(15) 0.0438(4) Uani 1 1 d . . . . .
N003 N 0.79894(17) 0.54838(11) 0.49617(15) 0.0449(4) Uani 1 1 d . . . . .
N004 N 0.62995(18) 0.56410(10) 0.63844(15) 0.0418(4) Uani 1 1 d . . . . .
C005 C 0.67011(19) 0.58313(11) 0.44855(17) 0.0385(4) Uani 1 1 d . . . . .
C006 C 0.29505(19) 0.70708(13) 0.08000(17) 0.0421(4) Uani 1 1 d . . . . .
C007 C 0.58544(19) 0.59121(11) 0.52081(17) 0.0367(4) Uani 1 1 d . . . . .
C008 C 0.48787(19) 0.65100(11) 0.27213(16) 0.0378(4) Uani 1 1 d . . . . .
C009 C 0.7583(2) 0.52746(11) 0.68541(17) 0.0407(4) Uani 1 1 d . . . . .
C00A C 0.61792(19) 0.61270(13) 0.32437(17) 0.0417(4) Uani 1 1 d . . . . .
H00A H 0.6724 0.6062 0.2773 0.050 Uiso 1 1 calc R . . . .
C00B C 0.8434(2) 0.52011(12) 0.61417(17) 0.0416(4) Uani 1 1 d . . . . .
C00C C 0.52368(19) 0.67553(12) 0.07893(17) 0.0411(4) Uani 1 1 d . . . . .
C00D C 0.44967(19) 0.62878(12) 0.46313(17) 0.0402(4) Uani 1 1 d . . . . .
H00D H 0.3920 0.6336 0.5076 0.048 Uiso 1 1 calc R . . . .
C00E C 0.40266(18) 0.65767(12) 0.34457(18) 0.0400(4) Uani 1 1 d . . . . .
H00E H 0.3136 0.6823 0.3095 0.048 Uiso 1 1 calc R . . . .
C00F C 0.2194(2) 0.66841(14) -0.03361(18) 0.0476(5) Uani 1 1 d . . . . .
C00G C 0.8093(2) 0.49297(14) 0.80775(18) 0.0497(5) Uani 1 1 d . . . . .
H00G H 0.7554 0.4974 0.8557 0.060 Uiso 1 1 calc R . . . .
C00H C 0.9369(3) 0.45365(14) 0.85438(19) 0.0543(5) Uani 1 1 d . . . . .
H00H H 0.9681 0.4300 0.9333 0.065 Uiso 1 1 calc R . . . .
C00I C 0.2351(2) 0.77280(14) 0.1164(2) 0.0505(5) Uani 1 1 d . . . . .
H00I H 0.2863 0.8000 0.1908 0.061 Uiso 1 1 calc R . . . .
C00J C 0.5542(3) 0.62571(15) -0.1036(2) 0.0558(5) Uani 1 1 d . . . . .
H00J H 0.5201 0.5963 -0.1780 0.067 Uiso 1 1 calc R . . . .
C00K C 0.6528(2) 0.71629(13) 0.11526(19) 0.0456(5) Uani 1 1 d . . . . .
H00K H 0.6851 0.7480 0.1874 0.055 Uiso 1 1 calc R . . . .
C00L C 0.9779(2) 0.48065(15) 0.6675(2) 0.0529(5) Uani 1 1 d . . . . .
H00L H 1.0354 0.4769 0.6226 0.063 Uiso 1 1 calc R . . . .
C00M C 0.4738(2) 0.63180(13) -0.03173(18) 0.0459(5) Uani 1 1 d . . . . .
C00N C 0.7334(2) 0.70976(15) 0.0440(2) 0.0538(5) Uani 1 1 d . . . . .
H00N H 0.8205 0.7365 0.0689 0.065 Uiso 1 1 calc R . . . .
C00O C 0.6845(3) 0.66352(16) -0.0640(2) 0.0577(6) Uani 1 1 d . . . . .
H00O H 0.7402 0.6580 -0.1102 0.069 Uiso 1 1 calc R . . . .
C00P C 1.0224(2) 0.44830(15) 0.7846(2) 0.0559(5) Uani 1 1 d . . . . .
H00P H 1.1103 0.4224 0.8191 0.067 Uiso 1 1 calc R . . . .
C00Q C 0.0227(2) 0.7586(2) -0.0697(3) 0.0711(8) Uani 1 1 d . . . . .
H00Q H -0.0695 0.7753 -0.1189 0.085 Uiso 1 1 calc R . . . .
C00R C 0.0977(2) 0.79784(17) 0.0411(3) 0.0641(7) Uani 1 1 d . . . . .
H00R H 0.0566 0.8414 0.0659 0.077 Uiso 1 1 calc R . . . .
C00S C 0.0830(2) 0.69410(19) -0.1089(2) 0.0637(7) Uani 1 1 d . . . . .
H00S H 0.0325 0.6684 -0.1848 0.076 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
S001 C00F 1.775(2) . ?
S001 C00M 1.773(2) . ?
N002 C006 1.429(2) . ?
N002 C008 1.396(2) . ?
N002 C00C 1.431(2) . ?
N003 C005 1.338(2) . ?
N003 C00B 1.348(2) . ?
N004 C007 1.338(2) . ?
N004 C009 1.348(3) . ?
C005 C007 1.433(3) . ?
C005 C00A 1.415(3) . ?
C006 C00F 1.394(3) . ?
C006 C00I 1.387(3) . ?
C007 C00D 1.422(3) . ?
C008 C00A 1.376(3) . ?
C008 C00E 1.437(3) . ?
C009 C00B 1.426(3) . ?
C009 C00G 1.427(3) . ?
C00A H00A 0.9300 . ?
C00B C00L 1.422(3) . ?
C00C C00K 1.388(3) . ?
C00C C00M 1.384(3) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.356(3) . ?
C00E H00E 0.9300 . ?
C00F C00S 1.388(3) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.361(3) . ?
C00H H00H 0.9300 . ?
C00H C00P 1.413(3) . ?
C00I H00I 0.9300 . ?
C00I C00R 1.392(3) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.390(3) . ?
C00J C00O 1.374(4) . ?
C00K H00K 0.9300 . ?
C00K C00N 1.387(3) . ?
C00L H00L 0.9300 . ?
C00L C00P 1.364(3) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.382(4) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.373(4) . ?
C00Q C00S 1.389(4) . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?

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
C00M S001 C00F 97.27(10) . . ?
C006 N002 C00C 114.12(15) . . ?
C008 N002 C006 124.58(16) . . ?
C008 N002 C00C 120.29(15) . . ?
C005 N003 C00B 116.71(16) . . ?
C007 N004 C009 116.52(16) . . ?
N003 C005 C007 121.38(17) . . ?
N003 C005 C00A 118.78(17) . . ?
C00A C005 C007 119.83(16) . . ?
C00F C006 N002 118.22(19) . . ?
C00I C006 N002 121.73(19) . . ?
C00I C006 C00F 119.82(18) . . ?
N004 C007 C005 122.08(17) . . ?
N004 C007 C00D 120.09(16) . . ?
C00D C007 C005 117.83(16) . . ?
N002 C008 C00E 120.41(16) . . ?
C00A C008 N002 120.92(16) . . ?
C00A C008 C00E 118.66(16) . . ?
N004 C009 C00B 121.50(17) . . ?
N004 C009 C00G 119.68(18) . . ?
C00B C009 C00G 118.79(18) . . ?
C005 C00A H00A 119.4 . . ?
C008 C00A C005 121.10(17) . . ?
C008 C00A H00A 119.4 . . ?
N003 C00B C009 121.79(17) . . ?
N003 C00B C00L 118.71(18) . . ?
C00L C00B C009 119.49(17) . . ?
C00K C00C N002 120.93(18) . . ?
C00M C00C N002 119.69(18) . . ?
C00M C00C C00K 119.29(18) . . ?
C007 C00D H00D 119.3 . . ?
C00E C00D C007 121.31(16) . . ?
C00E C00D H00D 119.3 . . ?
C008 C00E H00E 119.4 . . ?
C00D C00E C008 121.22(16) . . ?
C00D C00E H00E 119.4 . . ?
C006 C00F S001 119.12(15) . . ?
C00S C00F S001 120.60(19) . . ?
C00S C00F C006 120.3(2) . . ?
C009 C00G H00G 120.0 . . ?
C00H C00G C009 120.1(2) . . ?
C00H C00G H00G 120.0 . . ?
C00G C00H H00H 119.5 . . ?
C00G C00H C00P 120.91(18) . . ?
C00P C00H H00H 119.5 . . ?
C006 C00I H00I 120.2 . . ?
C006 C00I C00R 119.6(2) . . ?
C00R C00I H00I 120.2 . . ?
C00M C00J H00J 120.3 . . ?
C00O C00J H00J 120.3 . . ?
C00O C00J C00M 119.4(2) . . ?
C00C C00K H00K 120.0 . . ?
C00N C00K C00C 120.0(2) . . ?
C00N C00K H00K 120.0 . . ?
C00B C00L H00L 120.1 . . ?
C00P C00L C00B 119.8(2) . . ?
C00P C00L H00L 120.1 . . ?
C00C C00M S001 118.18(15) . . ?
C00C C00M C00J 120.7(2) . . ?
C00J C00M S001 121.07(17) . . ?
C00K C00N H00N 120.0 . . ?
C00O C00N C00K 120.0(2) . . ?
C00O C00N H00N 120.0 . . ?
C00J C00O C00N 120.49(19) . . ?
C00J C00O H00O 119.8 . . ?
C00N C00O H00O 119.8 . . ?
C00H C00P H00P 119.5 . . ?
C00L C00P C00H 120.9(2) . . ?
C00L C00P H00P 119.5 . . ?
C00R C00Q H00Q 119.7 . . ?
C00R C00Q C00S 120.6(2) . . ?
C00S C00Q H00Q 119.7 . . ?
C00I C00R H00R 119.9 . . ?
C00Q C00R C00I 120.3(2) . . ?
C00Q C00R H00R 119.9 . . ?
C00F C00S C00Q 119.3(2) . . ?
C00F C00S H00S 120.3 . . ?
C00Q C00S H00S 120.3 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-06-17
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.775
####################################################################### 
# 
# 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_mo_zhx_4223_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2110954'
loop_
_audit_author_name
_audit_author_address
'zhang huaxing'
;sichuan university
China
;
_audit_update_record             
;
2021-09-21 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_audit_creation_date             2021-05-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H10 N2 O'
_chemical_formula_sum            'C18 H10 N2 O'
_chemical_formula_weight         270.28
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   25.483(3)
_cell_length_b                   3.8577(3)
_cell_length_c                   25.757(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2532.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      23.337
_cell_measurement_theta_min      2.248
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0869 before and 0.0724 after correction.
The Ratio of minimum to maximum transmission is 0.8873.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1241
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            34196
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.248
_diffrn_ambient_temperature      302.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.957
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2804
_reflns_number_total             5773
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5773
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1727
_refine_ls_R_factor_gt           0.0810
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1244P)²+0.8615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2076
_refine_ls_wR_factor_ref         0.2710
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C37-C38
 1.4 with sigma of 0.01
 C33-C19
 1.4 with sigma of 0.01
 C20-C19
 1.4 with sigma of 0.01
 C28-C29
 1.4 with sigma of 0.01
 C28-C27
 1.4 with sigma of 0.01
 C27-C26
 1.4 with sigma of 0.01
 C19-C20
 1.4 with sigma of 0.01
 C19-C33
 1.4 with sigma of 0.01
 C33-C32
 1.4 with sigma of 0.01
 C21-C22
 1.38 with sigma of 0.01
3. Rigid bond restraints
 N23, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N23 \\sim C22: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C27(H27), C28(H28), C29(H29), C32(H32),
  C33(H33), C34(H34), C37(H37), C38(H38)
;
_atom_sites_solution_hydrogens   geom
_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 -0.4365(2) -0.3600(19) -0.4851(3) 0.0641(17) Uani 1 1 d . . . . .
N1 N -0.4777(3) -0.389(2) -0.6925(3) 0.0600(19) Uani 1 1 d . . . . .
N2 N -0.5512(3) -0.6499(19) -0.6187(3) 0.0562(19) Uani 1 1 d . . . . .
O3 O -0.3129(3) -0.6622(18) -0.5169(3) 0.0696(19) Uani 1 1 d . . . . .
C1 C -0.5809(5) -0.704(3) -0.7744(5) 0.076(4) Uani 1 1 d . . . . .
H1 H -0.5881 -0.7260 -0.8096 0.091 Uiso 1 1 calc R U . . .
C2 C -0.5361(4) -0.566(2) -0.7610(4) 0.067(3) Uani 1 1 d . . . . .
H2 H -0.5127 -0.4899 -0.7863 0.081 Uiso 1 1 calc R U . . .
C3 C -0.5235(3) -0.532(2) -0.7074(3) 0.055(2) Uani 1 1 d . . . . .
C4 C -0.4682(3) -0.378(2) -0.6421(4) 0.054(2) Uani 1 1 d . . . . .
C5 C -0.5051(3) -0.5116(19) -0.6040(3) 0.049(2) Uani 1 1 d . . . . .
C6 C -0.4916(3) -0.497(2) -0.5522(4) 0.049(2) Uani 1 1 d . . . . .
C7 C -0.5163(3) -0.613(2) -0.5028(3) 0.051(2) Uani 1 1 d . . . . .
C8 C -0.4808(3) -0.519(2) -0.4639(4) 0.056(2) Uani 1 1 d . . . . .
C9 C -0.4881(4) -0.589(3) -0.4131(4) 0.066(2) Uani 1 1 d . . . . .
H9 H -0.4627 -0.5316 -0.3887 0.079 Uiso 1 1 calc R U . . .
C10 C -0.5345(5) -0.751(2) -0.3983(5) 0.066(3) Uani 1 1 d . . . . .
H10 H -0.5411 -0.8002 -0.3636 0.079 Uiso 1 1 calc R U . . .
C11 C -0.5609(4) -0.666(2) -0.6700(3) 0.049(2) Uani 1 1 d . . . . .
C12 C -0.6095(4) -0.802(3) -0.6891(4) 0.062(3) Uani 1 1 d . . . . .
H12 H -0.6348 -0.8768 -0.6656 0.074 Uiso 1 1 calc R U . . .
C13 C -0.6190(5) -0.823(3) -0.7390(5) 0.080(3) Uani 1 1 d . . . . .
H13 H -0.6505 -0.9147 -0.7509 0.096 Uiso 1 1 calc R U . . .
C14 C -0.4199(4) -0.228(2) -0.6236(4) 0.053(3) Uani 1 1 d . . . . .
H14 H -0.3962 -0.1415 -0.6478 0.064 Uiso 1 1 calc R U . . .
C15 C -0.4079(4) -0.208(2) -0.5737(5) 0.057(3) Uani 1 1 d . . . . .
H15 H -0.3769 -0.1053 -0.5625 0.068 Uiso 1 1 calc R U . . .
C16 C -0.4447(3) -0.352(2) -0.5378(4) 0.050(2) Uani 1 1 d . . . . .
C17 C -0.5712(4) -0.837(3) -0.4372(4) 0.062(3) Uani 1 1 d . . . . .
H17 H -0.6028 -0.9409 -0.4277 0.074 Uiso 1 1 calc R U . . .
C18 C -0.5614(5) -0.772(2) -0.4886(5) 0.065(3) Uani 1 1 d . . . . .
H18 H -0.5858 -0.8370 -0.5137 0.078 Uiso 1 1 calc R U . . .
C19 C -0.1705(5) -0.236(3) -0.2282(5) 0.081(4) Uani 1 1 d D . . . .
H19 H -0.1628 -0.1973 -0.1934 0.097 Uiso 1 1 calc R U . . .
C20 C -0.2173(4) -0.387(3) -0.2417(4) 0.074(3) Uani 1 1 d D . . . .
H20 H -0.2403 -0.4618 -0.2160 0.089 Uiso 1 1 calc R U . . .
C21 C -0.2309(3) -0.432(2) -0.2947(4) 0.060(2) Uani 1 1 d D . . . .
C22 C -0.1949(4) -0.324(3) -0.3325(4) 0.063(3) Uani 1 1 d D U . . .
N23 N -0.2010(3) -0.342(2) -0.3845(3) 0.066(2) Uani 1 1 d . U . . .
C24 C -0.2465(3) -0.4888(19) -0.3985(5) 0.067(3) Uani 1 1 d . . . . .
C25 C -0.2584(4) -0.511(2) -0.4516(4) 0.062(2) Uani 1 1 d . . . . .
C26 C -0.2328(3) -0.401(2) -0.5013(3) 0.054(2) Uani 1 1 d D . . . .
C27 C -0.1871(4) -0.241(2) -0.5156(4) 0.055(3) Uani 1 1 d D . . . .
H27 H -0.1628 -0.1672 -0.4911 0.066 Uiso 1 1 calc R U . . .
C28 C -0.1789(4) -0.194(3) -0.5681(5) 0.074(3) Uani 1 1 d D . . . .
H28 H -0.1477 -0.0948 -0.5794 0.089 Uiso 1 1 calc R U . . .
C29 C -0.2161(6) -0.290(3) -0.6041(5) 0.085(4) Uani 1 1 d D . . . .
H29 H -0.2097 -0.2458 -0.6391 0.102 Uiso 1 1 calc R U . . .
N30 N -0.2763(3) -0.588(2) -0.3077(4) 0.074(2) Uani 1 1 d . . . . .
C31 C -0.2839(4) -0.615(2) -0.3600(4) 0.060(2) Uani 1 1 d . . . . .
C32 C -0.1476(5) -0.175(3) -0.3173(5) 0.078(3) Uani 1 1 d D . . . .
H32 H -0.1242 -0.0979 -0.3425 0.093 Uiso 1 1 calc R U . . .
C33 C -0.1350(5) -0.141(3) -0.2658(5) 0.085(3) Uani 1 1 d D . . . .
H33 H -0.1024 -0.0525 -0.2562 0.102 Uiso 1 1 calc R U . . .
C34 C -0.2627(4) -0.450(2) -0.5901(4) 0.068(3) Uani 1 1 d . . . . .
H34 H -0.2880 -0.5154 -0.6142 0.081 Uiso 1 1 calc R U . . .
C35 C -0.2683(3) -0.503(2) -0.5379(3) 0.054(2) Uani 1 1 d . . . . .
C36 C -0.3049(4) -0.659(2) -0.4647(5) 0.067(3) Uani 1 1 d . . . . .
C37 C -0.3418(4) -0.797(2) -0.4284(5) 0.063(3) Uani 1 1 d D . . . .
H37 H -0.3724 -0.9021 -0.4401 0.076 Uiso 1 1 calc R U . . .
C38 C -0.3314(4) -0.773(2) -0.3763(6) 0.068(4) Uani 1 1 d D . . . .
H38 H -0.3551 -0.8592 -0.3521 0.082 Uiso 1 1 calc R U . . .


_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 C8 1.395(11) . ?
O1 C16 1.375(11) . ?
N1 C3 1.348(11) . ?
N1 C4 1.320(11) . ?
N2 C5 1.346(10) . ?
N2 C11 1.346(11) . ?
O3 C35 1.402(11) . ?
O3 C36 1.360(13) . ?
C1 H1 0.9300 . ?
C1 C2 1.306(14) . ?
C1 C13 1.409(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.425(12) . ?
C3 C11 1.451(12) . ?
C4 C5 1.453(11) . ?
C4 C14 1.439(13) . ?
C5 C6 1.379(11) . ?
C6 C7 1.488(13) . ?
C6 C16 1.371(12) . ?
C7 C8 1.399(12) . ?
C7 C18 1.353(13) . ?
C8 C9 1.349(13) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(14) . ?
C10 H10 0.9300 . ?
C10 C17 1.412(14) . ?
C11 C12 1.431(14) . ?
C12 H12 0.9300 . ?
C12 C13 1.311(14) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.324(14) . ?
C15 H15 0.9300 . ?
C15 C16 1.428(14) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(14) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.375(9) . ?
C19 C33 1.375(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.416(14) . ?
C21 C22 1.402(10) . ?
C21 N30 1.348(11) . ?
C22 N23 1.350(12) . ?
C22 C32 1.390(16) . ?
N23 C24 1.340(12) . ?
C24 C25 1.405(15) . ?
C24 C31 1.459(14) . ?
C25 C26 1.498(14) . ?
C25 C36 1.357(13) . ?
C26 C27 1.368(10) . ?
C26 C35 1.363(12) . ?
C27 H27 0.9300 . ?
C27 C28 1.381(11) . ?
C28 H28 0.9300 . ?
C28 C29 1.376(12) . ?
C29 H29 0.9300 . ?
C29 C34 1.386(16) . ?
N30 C31 1.364(12) . ?
C31 C38 1.420(14) . ?
C32 H32 0.9300 . ?
C32 C33 1.373(11) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C34 C35 1.368(12) . ?
C36 C37 1.428(15) . ?
C37 H37 0.9300 . ?
C37 C38 1.371(12) . ?
C38 H38 0.9300 . ?

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
C16 O1 C8 105.8(7) . . ?
C4 N1 C3 116.8(8) . . ?
C5 N2 C11 117.0(8) . . ?
C36 O3 C35 104.8(8) . . ?
C2 C1 H1 117.8 . . ?
C2 C1 C13 124.4(11) . . ?
C13 C1 H1 117.8 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.3(10) . . ?
C3 C2 H2 120.3 . . ?
N1 C3 C2 120.6(8) . . ?
N1 C3 C11 121.7(8) . . ?
C2 C3 C11 117.6(8) . . ?
N1 C4 C5 122.3(8) . . ?
N1 C4 C14 119.5(8) . . ?
C14 C4 C5 118.1(9) . . ?
N2 C5 C4 121.0(8) . . ?
N2 C5 C6 120.4(7) . . ?
C6 C5 C4 118.6(7) . . ?
C5 C6 C7 135.1(7) . . ?
C16 C6 C5 119.6(8) . . ?
C16 C6 C7 105.2(8) . . ?
C8 C7 C6 105.0(7) . . ?
C18 C7 C6 136.7(9) . . ?
C18 C7 C8 118.4(10) . . ?
O1 C8 C7 111.1(8) . . ?
C9 C8 O1 125.3(9) . . ?
C9 C8 C7 123.5(9) . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.3(10) . . ?
C10 C9 H9 120.8 . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C17 118.4(11) . . ?
C17 C10 H10 120.8 . . ?
N2 C11 C3 121.0(8) . . ?
N2 C11 C12 120.8(9) . . ?
C12 C11 C3 118.1(8) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.3(10) . . ?
C13 C12 H12 119.3 . . ?
C1 C13 H13 120.4 . . ?
C12 C13 C1 119.2(11) . . ?
C12 C13 H13 120.4 . . ?
C4 C14 H14 118.6 . . ?
C15 C14 C4 122.7(10) . . ?
C15 C14 H14 118.6 . . ?
C14 C15 H15 121.4 . . ?
C14 C15 C16 117.1(10) . . ?
C16 C15 H15 121.4 . . ?
O1 C16 C15 123.3(9) . . ?
C6 C16 O1 113.0(8) . . ?
C6 C16 C15 123.7(10) . . ?
C10 C17 H17 119.3 . . ?
C18 C17 C10 121.4(11) . . ?
C18 C17 H17 119.3 . . ?
C7 C18 C17 119.9(11) . . ?
C7 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 H19 119.8 . . ?
C33 C19 H19 119.8 . . ?
C33 C19 C20 120.4(12) . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.5(10) . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 118.3(9) . . ?
N30 C21 C20 120.2(9) . . ?
N30 C21 C22 121.5(10) . . ?
N23 C22 C21 126.8(10) . . ?
N23 C22 C32 113.6(9) . . ?
C32 C22 C21 119.6(10) . . ?
C24 N23 C22 112.8(9) . . ?
N23 C24 C25 118.3(9) . . ?
N23 C24 C31 121.6(11) . . ?
C25 C24 C31 120.0(8) . . ?
C24 C25 C26 136.1(8) . . ?
C36 C25 C24 117.1(10) . . ?
C36 C25 C26 106.7(10) . . ?
C27 C26 C25 136.7(9) . . ?
C35 C26 C25 102.7(8) . . ?
C35 C26 C27 120.6(9) . . ?
C26 C27 H27 121.6 . . ?
C26 C27 C28 116.8(10) . . ?
C28 C27 H27 121.6 . . ?
C27 C28 H28 119.3 . . ?
C29 C28 C27 121.4(11) . . ?
C29 C28 H28 119.3 . . ?
C28 C29 H29 118.9 . . ?
C28 C29 C34 122.2(12) . . ?
C34 C29 H29 118.9 . . ?
C21 N30 C31 113.6(8) . . ?
N30 C31 C24 123.6(9) . . ?
N30 C31 C38 116.5(10) . . ?
C38 C31 C24 120.0(11) . . ?
C22 C32 H32 119.5 . . ?
C33 C32 C22 121.0(11) . . ?
C33 C32 H32 119.5 . . ?
C19 C33 H33 119.9 . . ?
C32 C33 C19 120.1(12) . . ?
C32 C33 H33 119.9 . . ?
C29 C34 H34 122.8 . . ?
C35 C34 C29 114.4(9) . . ?
C35 C34 H34 122.8 . . ?
C26 C35 O3 113.5(8) . . ?
C26 C35 C34 124.5(9) . . ?
C34 C35 O3 122.0(9) . . ?
O3 C36 C37 122.9(10) . . ?
C25 C36 O3 112.4(10) . . ?
C25 C36 C37 124.7(12) . . ?
C36 C37 H37 120.4 . . ?
C38 C37 C36 119.2(11) . . ?
C38 C37 H37 120.4 . . ?
C31 C38 H38 120.6 . . ?
C37 C38 C31 118.9(11) . . ?
C37 C38 H38 120.6 . . ?

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 C8 C9 C10 -179.7(8) . . . . ?
N1 C3 C11 N2 0.6(13) . . . . ?
N1 C3 C11 C12 177.7(8) . . . . ?
N1 C4 C5 N2 -0.8(12) . . . . ?
N1 C4 C5 C6 178.5(8) . . . . ?
N1 C4 C14 C15 179.9(9) . . . . ?
N2 C5 C6 C7 1.9(13) . . . . ?
N2 C5 C6 C16 -179.1(7) . . . . ?
N2 C11 C12 C13 -179.1(10) . . . . ?
O3 C36 C37 C38 -177.9(9) . . . . ?
C1 C2 C3 N1 -179.8(9) . . . . ?
C1 C2 C3 C11 2.2(14) . . . . ?
C2 C1 C13 C12 -1.4(19) . . . . ?
C2 C3 C11 N2 178.6(8) . . . . ?
C2 C3 C11 C12 -4.3(12) . . . . ?
C3 N1 C4 C5 -0.2(12) . . . . ?
C3 N1 C4 C14 -179.9(7) . . . . ?
C3 C11 C12 C13 3.8(14) . . . . ?
C4 N1 C3 C2 -177.7(8) . . . . ?
C4 N1 C3 C11 0.2(12) . . . . ?
C4 C5 C6 C7 -177.5(8) . . . . ?
C4 C5 C6 C16 1.5(11) . . . . ?
C4 C14 C15 C16 1.6(14) . . . . ?
C5 N2 C11 C3 -1.5(12) . . . . ?
C5 N2 C11 C12 -178.6(8) . . . . ?
C5 C4 C14 C15 0.1(13) . . . . ?
C5 C6 C7 C8 179.5(9) . . . . ?
C5 C6 C7 C18 -1.0(16) . . . . ?
C5 C6 C16 O1 -179.2(7) . . . . ?
C5 C6 C16 C15 0.2(12) . . . . ?
C6 C7 C8 O1 -0.7(9) . . . . ?
C6 C7 C8 C9 -177.7(8) . . . . ?
C6 C7 C18 C17 -179.6(9) . . . . ?
C7 C6 C16 O1 0.0(9) . . . . ?
C7 C6 C16 C15 179.5(8) . . . . ?
C7 C8 C9 C10 -3.1(14) . . . . ?
C8 O1 C16 C6 -0.4(10) . . . . ?
C8 O1 C16 C15 -179.9(7) . . . . ?
C8 C7 C18 C17 -0.2(13) . . . . ?
C8 C9 C10 C17 1.0(14) . . . . ?
C9 C10 C17 C18 1.3(15) . . . . ?
C10 C17 C18 C7 -1.8(15) . . . . ?
C11 N2 C5 C4 1.6(11) . . . . ?
C11 N2 C5 C6 -177.7(7) . . . . ?
C11 C12 C13 C1 -0.9(17) . . . . ?
C13 C1 C2 C3 0.7(18) . . . . ?
C14 C4 C5 N2 179.0(7) . . . . ?
C14 C4 C5 C6 -1.7(11) . . . . ?
C14 C15 C16 O1 177.6(8) . . . . ?
C14 C15 C16 C6 -1.8(13) . . . . ?
C16 O1 C8 C7 0.7(9) . . . . ?
C16 O1 C8 C9 177.7(9) . . . . ?
C16 C6 C7 C8 0.4(9) . . . . ?
C16 C6 C7 C18 179.9(9) . . . . ?
C18 C7 C8 O1 179.7(7) . . . . ?
C18 C7 C8 C9 2.7(13) . . . . ?
C19 C20 C21 C22 1.4(14) . . . . ?
C19 C20 C21 N30 178.4(8) . . . . ?
C20 C19 C33 C32 4.4(17) . . . . ?
C20 C21 C22 N23 -179.4(9) . . . . ?
C20 C21 C22 C32 -0.7(13) . . . . ?
C20 C21 N30 C31 -179.4(8) . . . . ?
C21 C22 N23 C24 -1.8(13) . . . . ?
C21 C22 C32 C33 1.8(16) . . . . ?
C21 N30 C31 C24 0.3(12) . . . . ?
C21 N30 C31 C38 -179.1(7) . . . . ?
C22 C21 N30 C31 -2.6(12) . . . . ?
C22 N23 C24 C25 177.6(8) . . . . ?
C22 N23 C24 C31 -0.6(11) . . . . ?
C22 C32 C33 C19 -3.6(18) . . . . ?
N23 C22 C32 C33 -179.3(10) . . . . ?
N23 C24 C25 C26 -1.6(14) . . . . ?
N23 C24 C25 C36 -179.6(8) . . . . ?
N23 C24 C31 N30 1.4(13) . . . . ?
N23 C24 C31 C38 -179.2(8) . . . . ?
C24 C25 C26 C27 1.6(17) . . . . ?
C24 C25 C26 C35 -178.5(9) . . . . ?
C24 C25 C36 O3 179.0(7) . . . . ?
C24 C25 C36 C37 -1.0(14) . . . . ?
C24 C31 C38 C37 -1.4(14) . . . . ?
C25 C24 C31 N30 -176.8(8) . . . . ?
C25 C24 C31 C38 2.5(12) . . . . ?
C25 C26 C27 C28 179.1(9) . . . . ?
C25 C26 C35 O3 0.2(9) . . . . ?
C25 C26 C35 C34 178.4(8) . . . . ?
C25 C36 C37 C38 2.2(15) . . . . ?
C26 C25 C36 O3 0.5(11) . . . . ?
C26 C25 C36 C37 -179.6(8) . . . . ?
C26 C27 C28 C29 2.8(14) . . . . ?
C27 C26 C35 O3 -179.9(7) . . . . ?
C27 C26 C35 C34 -1.7(13) . . . . ?
C27 C28 C29 C34 -2.4(15) . . . . ?
C28 C29 C34 C35 0.0(13) . . . . ?
C29 C34 C35 O3 -179.9(8) . . . . ?
C29 C34 C35 C26 2.1(13) . . . . ?
N30 C21 C22 N23 3.7(14) . . . . ?
N30 C21 C22 C32 -177.6(9) . . . . ?
N30 C31 C38 C37 178.0(9) . . . . ?
C31 C24 C25 C26 176.7(9) . . . . ?
C31 C24 C25 C36 -1.3(12) . . . . ?
C32 C22 N23 C24 179.4(8) . . . . ?
C33 C19 C20 C21 -3.3(16) . . . . ?
C35 O3 C36 C25 -0.3(10) . . . . ?
C35 O3 C36 C37 179.7(8) . . . . ?
C35 C26 C27 C28 -0.8(12) . . . . ?
C36 O3 C35 C26 0.1(10) . . . . ?
C36 O3 C35 C34 -178.2(8) . . . . ?
C36 C25 C26 C27 179.8(9) . . . . ?
C36 C25 C26 C35 -0.4(9) . . . . ?
C36 C37 C38 C31 -0.8(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_zhx_4212_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2110953'
loop_
_audit_author_name
_audit_author_address
'zhang huaxing'
;sichuan university
China
;
_audit_update_record             
;
2021-09-21 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_audit_creation_date             2021-04-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C60 H42 N5'
_chemical_formula_sum            'C60 H42 N5'
_chemical_formula_weight         832.98
_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'

_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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   9.5511(3)
_cell_length_b                   13.5323(3)
_cell_length_c                   37.4313(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.885(2)
_cell_angle_gamma                90
_cell_volume                     4826.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      68.385
_cell_measurement_theta_min      2.366
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1427 before and 0.0691 after correction.
The Ratio of minimum to maximum transmission is 0.6941.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1748
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            39694
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.380
_diffrn_reflns_theta_min         2.366
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6214
_reflns_number_total             8794
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         8794
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1012P)²+1.2798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1955
_refine_ls_wR_factor_ref         0.2159
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C61, C62
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C61 \\sim C62: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.02 within 2A
Uanis(C61) = Uanis(C62)
4.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C61(H61), C7(H7), C8(H8), C11(H11), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C37(H37),
 C38(H38), C39(H39), C40(H40), C43(H43), C44(H44), C46(H46), C47(H47), C50(H50),
  C51(H51), C52(H52), C53(H53), C54(H54), C56(H56), C57(H57), C58(H58),
 C59(H59), C60(H60)
;
_atom_sites_solution_hydrogens   geom
_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
N1 N 0.33514(19) 0.46027(14) 0.32485(5) 0.0470(4) Uani 1 1 d . . . . .
N5 N 0.3865(2) 0.26798(15) 0.29766(6) 0.0534(5) Uani 1 1 d . . . . .
N2 N 0.1855(2) 0.32129(16) 0.42971(5) 0.0536(5) Uani 1 1 d . . . . .
C3 C 0.4861(2) 0.52028(18) 0.24049(6) 0.0489(5) Uani 1 1 d . . . . .
C4 C 0.2212(2) 0.46653(18) 0.40075(6) 0.0482(5) Uani 1 1 d . . . . .
C1 C 0.8782(7) 0.0838(8) 0.0612(3) 0.189(5) Uani 1 1 d . . . . .
H1 H 0.8986 0.0204 0.0535 0.227 Uiso 1 1 calc R U . . .
C2 C 0.8832(5) 0.1015(4) 0.0958(2) 0.146(2) Uani 1 1 d . . . . .
H2 H 0.9044 0.0509 0.1121 0.175 Uiso 1 1 calc R U . . .
C61 C 0.8567(3) 0.1964(3) 0.10778(12) 0.0962(8) Uani 1 1 d . U . . .
H61 H 0.8617 0.2085 0.1323 0.115 Uiso 1 1 calc R U . . .
C62 C 0.8230(3) 0.2737(4) 0.08442(11) 0.0962(8) Uani 1 1 d . U . . .
N3 N 0.7952(3) 0.3697(2) 0.09801(7) 0.0802(8) Uani 1 1 d . . . . .
C6 C 0.7323(3) 0.3783(2) 0.13136(7) 0.0630(7) Uani 1 1 d . . . . .
C7 C 0.7854(3) 0.4452(2) 0.15700(8) 0.0660(7) Uani 1 1 d . . . . .
H7 H 0.8663 0.4807 0.1531 0.079 Uiso 1 1 calc R U . . .
C8 C 0.7186(3) 0.4591(2) 0.18815(7) 0.0600(6) Uani 1 1 d . . . . .
H8 H 0.7552 0.5044 0.2050 0.072 Uiso 1 1 calc R U . . .
C9 C 0.5977(2) 0.40685(19) 0.19497(6) 0.0512(5) Uani 1 1 d . . . . .
C10 C 0.5215(2) 0.42295(19) 0.22778(6) 0.0493(5) Uani 1 1 d . . . . .
C11 C 0.4841(3) 0.34185(19) 0.24712(7) 0.0532(6) Uani 1 1 d . . . . .
H11 H 0.5028 0.2791 0.2385 0.064 Uiso 1 1 calc R U . . .
C12 C 0.4181(2) 0.35050(17) 0.27967(6) 0.0480(5) Uani 1 1 d . . . . .
C13 C 0.3339(2) 0.28125(17) 0.32944(6) 0.0493(5) Uani 1 1 d . . . . .
C14 C 0.3001(3) 0.19526(18) 0.34953(7) 0.0576(6) Uani 1 1 d . . . . .
H14 H 0.3112 0.1329 0.3396 0.069 Uiso 1 1 calc R U . . .
C15 C 0.2528(3) 0.20309(19) 0.38245(7) 0.0576(6) Uani 1 1 d . . . . .
H15 H 0.2323 0.1470 0.3954 0.069 Uiso 1 1 calc R U . . .
C16 C 0.2347(2) 0.29879(18) 0.39692(6) 0.0488(5) Uani 1 1 d . . . . .
C17 C 0.1721(3) 0.25230(19) 0.45811(6) 0.0523(6) Uani 1 1 d . . . . .
C18 C 0.2867(3) 0.1962(2) 0.46960(7) 0.0632(7) Uani 1 1 d . . . . .
H18 H 0.3713 0.2037 0.4590 0.076 Uiso 1 1 calc R U . . .
C19 C 0.2754(4) 0.1289(3) 0.49684(9) 0.0795(9) Uani 1 1 d . . . . .
H19 H 0.3523 0.0902 0.5043 0.095 Uiso 1 1 calc R U . . .
C20 C 0.1516(4) 0.1186(3) 0.51299(9) 0.0823(9) Uani 1 1 d . . . . .
H20 H 0.1452 0.0740 0.5317 0.099 Uiso 1 1 calc R U . . .
C21 C 0.0474(3) 0.2414(2) 0.47370(8) 0.0675(7) Uani 1 1 d . . . . .
H21 H -0.0303 0.2787 0.4657 0.081 Uiso 1 1 calc R U . . .
C22 C 0.0376(4) 0.1742(3) 0.50145(9) 0.0826(10) Uani 1 1 d . . . . .
H22 H -0.0467 0.1669 0.5122 0.099 Uiso 1 1 calc R U . . .
C23 C 0.8434(5) 0.1564(7) 0.03558(18) 0.175(4) Uani 1 1 d . . . . .
H23A H 0.7600 0.1342 0.0216 0.209 Uiso 1 1 calc R U . . .
H23B H 0.9187 0.1589 0.0195 0.209 Uiso 1 1 calc R U . . .
C24 C 0.8175(4) 0.2572(5) 0.04725(12) 0.140(2) Uani 1 1 d . . . . .
H24 H 0.7984 0.3080 0.0309 0.168 Uiso 1 1 calc R U . . .
C25 C 0.8205(3) 0.4575(3) 0.07915(8) 0.0874(11) Uani 1 1 d . . . . .
C26 C 0.9415(4) 0.4687(5) 0.06146(10) 0.1179(18) Uani 1 1 d . . . . .
H26 H 1.0062 0.4173 0.0616 0.141 Uiso 1 1 calc R U . . .
C27 C 0.9673(6) 0.5530(6) 0.04405(14) 0.161(3) Uani 1 1 d . . . . .
H27 H 1.0498 0.5593 0.0324 0.193 Uiso 1 1 calc R U . . .
C28 C 0.8755(7) 0.6282(6) 0.04334(17) 0.170(3) Uani 1 1 d . . . . .
H28 H 0.8945 0.6858 0.0310 0.204 Uiso 1 1 calc R U . . .
C29 C 0.7492(6) 0.6205(5) 0.06135(16) 0.150(2) Uani 1 1 d . . . . .
H29 H 0.6858 0.6727 0.0613 0.180 Uiso 1 1 calc R U . . .
C30 C 0.7240(4) 0.5339(4) 0.07871(11) 0.1077(15) Uani 1 1 d . . . . .
H30 H 0.6415 0.5264 0.0903 0.129 Uiso 1 1 calc R U . . .
C31 C 0.6149(3) 0.3241(2) 0.13823(7) 0.0626(7) Uani 1 1 d . . . . .
H31 H 0.5790 0.2783 0.1215 0.075 Uiso 1 1 calc R U . . .
C32 C 0.5502(3) 0.3371(2) 0.16973(7) 0.0553(6) Uani 1 1 d . . . . .
H32 H 0.4729 0.2983 0.1742 0.066 Uiso 1 1 calc R U . . .
C33 C 0.4222(2) 0.52885(18) 0.27198(6) 0.0504(5) Uani 1 1 d . . . . .
H33 H 0.3989 0.5916 0.2798 0.060 Uiso 1 1 calc R U . . .
C34 C 0.3901(2) 0.44628(17) 0.29308(6) 0.0453(5) Uani 1 1 d . . . . .
C35 C 0.3100(2) 0.37878(16) 0.34351(6) 0.0443(5) Uani 1 1 d . . . . .
C36 C 0.2583(2) 0.38501(17) 0.37821(6) 0.0457(5) Uani 1 1 d . . . . .
C37 C 0.2230(3) 0.56895(19) 0.39754(7) 0.0570(6) Uani 1 1 d . . . . .
H37 H 0.2519 0.5987 0.3769 0.068 Uiso 1 1 calc R U . . .
C38 C 0.1812(3) 0.6256(2) 0.42555(8) 0.0679(7) Uani 1 1 d . . . . .
H38 H 0.1806 0.6941 0.4234 0.081 Uiso 1 1 calc R U . . .
C39 C 0.1402(3) 0.5824(2) 0.45687(8) 0.0689(7) Uani 1 1 d . . . . .
H39 H 0.1133 0.6226 0.4754 0.083 Uiso 1 1 calc R U . . .
C40 C 0.1384(3) 0.4812(2) 0.46105(7) 0.0614(6) Uani 1 1 d . . . . .
H40 H 0.1123 0.4524 0.4821 0.074 Uiso 1 1 calc R U . . .
C41 C 0.1772(2) 0.42393(19) 0.43254(6) 0.0514(5) Uani 1 1 d . . . . .
C42 C 0.5113(3) 0.61235(18) 0.22024(6) 0.0523(6) Uani 1 1 d . . . . .
C43 C 0.4788(3) 0.6188(2) 0.18336(7) 0.0588(6) Uani 1 1 d . . . . .
H43 H 0.4451 0.5635 0.1708 0.071 Uiso 1 1 calc R U . . .
C44 C 0.4962(3) 0.7063(2) 0.16542(7) 0.0665(7) Uani 1 1 d . . . . .
H44 H 0.4769 0.7086 0.1407 0.080 Uiso 1 1 calc R U . . .
C45 C 0.5418(3) 0.7907(2) 0.18332(8) 0.0671(7) Uani 1 1 d . . . . .
C46 C 0.5751(3) 0.7854(2) 0.22016(8) 0.0714(8) Uani 1 1 d . . . . .
H46 H 0.6064 0.8413 0.2327 0.086 Uiso 1 1 calc R U . . .
C47 C 0.5613(3) 0.6968(2) 0.23787(7) 0.0641(7) Uani 1 1 d . . . . .
H47 H 0.5862 0.6936 0.2623 0.077 Uiso 1 1 calc R U . . .
N48 N 0.5558(3) 0.8815(2) 0.16497(8) 0.0845(8) Uani 1 1 d . . . . .
C49 C 0.6685(4) 0.9453(2) 0.17572(9) 0.0817(9) Uani 1 1 d . . . . .
C50 C 0.6452(6) 1.0435(3) 0.18331(12) 0.1039(13) Uani 1 1 d . . . . .
H50 H 0.5550 1.0694 0.1802 0.125 Uiso 1 1 calc R U . . .
C51 C 0.7543(8) 1.1027(4) 0.19534(15) 0.1268(18) Uani 1 1 d . . . . .
H51 H 0.7381 1.1690 0.2002 0.152 Uiso 1 1 calc R U . . .
C52 C 0.8863(7) 1.0653(5) 0.20032(16) 0.137(2) Uani 1 1 d . . . . .
H52 H 0.9595 1.1062 0.2088 0.165 Uiso 1 1 calc R U . . .
C53 C 0.9127(6) 0.9689(4) 0.19306(16) 0.1284(18) Uani 1 1 d . . . . .
H53 H 1.0033 0.9438 0.1965 0.154 Uiso 1 1 calc R U . . .
C54 C 0.8023(5) 0.9078(3) 0.18041(13) 0.1038(13) Uani 1 1 d . . . . .
H54 H 0.8193 0.8419 0.1752 0.125 Uiso 1 1 calc R U . . .
C55 C 0.4575(4) 0.9074(2) 0.13647(8) 0.0720(8) Uani 1 1 d . . . . .
C56 C 0.3187(4) 0.8833(3) 0.13741(11) 0.0906(10) Uani 1 1 d . . . . .
H56 H 0.2883 0.8521 0.1576 0.109 Uiso 1 1 calc R U . . .
C57 C 0.2227(5) 0.9041(3) 0.10935(14) 0.1070(13) Uani 1 1 d . . . . .
H57 H 0.1291 0.8863 0.1105 0.128 Uiso 1 1 calc R U . . .
C58 C 0.2668(6) 0.9514(3) 0.07963(13) 0.1065(14) Uani 1 1 d . . . . .
H58 H 0.2036 0.9645 0.0602 0.128 Uiso 1 1 calc R U . . .
C59 C 0.4029(5) 0.9789(3) 0.07872(10) 0.0974(13) Uani 1 1 d . . . . .
H59 H 0.4314 1.0130 0.0589 0.117 Uiso 1 1 calc R U . . .
C60 C 0.5009(5) 0.9573(3) 0.10684(10) 0.0857(10) Uani 1 1 d . . . . .
H60 H 0.5942 0.9760 0.1058 0.103 Uiso 1 1 calc R U . . .


_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 C34 1.346(3) . ?
N1 C35 1.336(3) . ?
N5 C12 1.349(3) . ?
N5 C13 1.334(3) . ?
N2 C16 1.378(3) . ?
N2 C17 1.427(3) . ?
N2 C41 1.396(3) . ?
C3 C10 1.448(4) . ?
C3 C33 1.369(3) . ?
C3 C42 1.486(3) . ?
C4 C36 1.448(3) . ?
C4 C37 1.391(4) . ?
C4 C41 1.411(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.313(10) . ?
C1 C23 1.398(13) . ?
C2 H2 0.9300 . ?
C2 C61 1.390(6) . ?
C61 H61 0.9300 . ?
C61 C62 1.387(6) . ?
C62 N3 1.427(5) . ?
C62 C24 1.407(6) . ?
N3 C6 1.426(3) . ?
N3 C25 1.412(5) . ?
C6 C7 1.389(4) . ?
C6 C31 1.379(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(4) . ?
C9 C10 1.485(3) . ?
C9 C32 1.389(4) . ?
C10 C11 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.414(3) . ?
C12 C34 1.422(3) . ?
C13 C14 1.434(3) . ?
C13 C35 1.445(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.345(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.419(4) . ?
C16 C36 1.387(3) . ?
C17 C18 1.377(4) . ?
C17 C21 1.370(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(5) . ?
C20 H20 0.9300 . ?
C20 C22 1.369(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(4) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.459(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.379(5) . ?
C25 C30 1.384(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.345(8) . ?
C27 H27 0.9300 . ?
C27 C28 1.342(10) . ?
C28 H28 0.9300 . ?
C28 C29 1.425(9) . ?
C29 H29 0.9300 . ?
C29 C30 1.369(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.379(3) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C33 C34 1.414(3) . ?
C35 C36 1.423(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.379(4) . ?
C38 H38 0.9300 . ?
C38 C39 1.390(4) . ?
C39 H39 0.9300 . ?
C39 C40 1.378(4) . ?
C40 H40 0.9300 . ?
C40 C41 1.389(4) . ?
C42 C43 1.397(4) . ?
C42 C47 1.388(4) . ?
C43 H43 0.9300 . ?
C43 C44 1.377(4) . ?
C44 H44 0.9300 . ?
C44 C45 1.379(4) . ?
C45 C46 1.396(4) . ?
C45 N48 1.419(3) . ?
C46 H46 0.9300 . ?
C46 C47 1.381(4) . ?
C47 H47 0.9300 . ?
N48 C49 1.416(4) . ?
N48 C55 1.416(4) . ?
C49 C50 1.381(5) . ?
C49 C54 1.375(6) . ?
C50 H50 0.9300 . ?
C50 C51 1.366(7) . ?
C51 H51 0.9300 . ?
C51 C52 1.360(8) . ?
C52 H52 0.9300 . ?
C52 C53 1.361(8) . ?
C53 H53 0.9300 . ?
C53 C54 1.397(7) . ?
C54 H54 0.9300 . ?
C55 C56 1.368(5) . ?
C55 C60 1.386(4) . ?
C56 H56 0.9300 . ?
C56 C57 1.375(6) . ?
C57 H57 0.9300 . ?
C57 C58 1.375(7) . ?
C58 H58 0.9300 . ?
C58 C59 1.354(7) . ?
C59 H59 0.9300 . ?
C59 C60 1.392(6) . ?
C60 H60 0.9300 . ?

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
C35 N1 C34 116.2(2) . . ?
C13 N5 C12 116.4(2) . . ?
C16 N2 C17 124.9(2) . . ?
C16 N2 C41 108.18(19) . . ?
C41 N2 C17 125.9(2) . . ?
C10 C3 C42 123.1(2) . . ?
C33 C3 C10 119.2(2) . . ?
C33 C3 C42 117.7(2) . . ?
C37 C4 C36 134.7(2) . . ?
C37 C4 C41 119.1(2) . . ?
C41 C4 C36 106.2(2) . . ?
C2 C1 H1 118.7 . . ?
C2 C1 C23 122.7(8) . . ?
C23 C1 H1 118.7 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C61 119.4(8) . . ?
C61 C2 H2 120.3 . . ?
C2 C61 H61 118.9 . . ?
C62 C61 C2 122.2(5) . . ?
C62 C61 H61 118.9 . . ?
C61 C62 N3 120.2(3) . . ?
C61 C62 C24 119.7(5) . . ?
C24 C62 N3 120.1(5) . . ?
C6 N3 C62 119.1(3) . . ?
C25 N3 C62 123.1(3) . . ?
C25 N3 C6 117.7(3) . . ?
C7 C6 N3 120.2(3) . . ?
C31 C6 N3 121.0(3) . . ?
C31 C6 C7 118.7(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.3 . . ?
C7 C8 C9 121.5(3) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 122.4(2) . . ?
C32 C9 C8 117.2(2) . . ?
C32 C9 C10 120.4(2) . . ?
C3 C10 C9 122.9(2) . . ?
C11 C10 C3 118.5(2) . . ?
C11 C10 C9 118.5(2) . . ?
C10 C11 H11 118.8 . . ?
C10 C11 C12 122.3(2) . . ?
C12 C11 H11 118.8 . . ?
N5 C12 C11 119.3(2) . . ?
N5 C12 C34 121.6(2) . . ?
C11 C12 C34 119.0(2) . . ?
N5 C13 C14 118.0(2) . . ?
N5 C13 C35 121.8(2) . . ?
C14 C13 C35 120.2(2) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.7 . . ?
C14 C15 C16 118.6(2) . . ?
C16 C15 H15 120.7 . . ?
N2 C16 C15 126.8(2) . . ?
N2 C16 C36 109.9(2) . . ?
C36 C16 C15 123.2(2) . . ?
C18 C17 N2 119.0(2) . . ?
C21 C17 N2 120.8(2) . . ?
C21 C17 C18 120.2(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.1 . . ?
C22 C20 C19 119.7(3) . . ?
C22 C20 H20 120.1 . . ?
C17 C21 H21 120.2 . . ?
C17 C21 C22 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C22 C21 120.2(3) . . ?
C20 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C1 C23 H23A 107.5 . . ?
C1 C23 H23B 107.5 . . ?
C1 C23 C24 119.3(6) . . ?
H23A C23 H23B 107.0 . . ?
C24 C23 H23A 107.5 . . ?
C24 C23 H23B 107.5 . . ?
C62 C24 C23 116.7(6) . . ?
C62 C24 H24 121.7 . . ?
C23 C24 H24 121.7 . . ?
C26 C25 N3 120.6(4) . . ?
C26 C25 C30 119.5(4) . . ?
C30 C25 N3 119.9(3) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.8(5) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.8(5) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.6(5) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 121.0 . . ?
C30 C29 C28 117.9(6) . . ?
C30 C29 H29 121.0 . . ?
C25 C30 H30 119.8 . . ?
C29 C30 C25 120.4(4) . . ?
C29 C30 H30 119.8 . . ?
C6 C31 H31 119.7 . . ?
C6 C31 C32 120.6(3) . . ?
C32 C31 H31 119.7 . . ?
C9 C32 H32 119.2 . . ?
C31 C32 C9 121.6(2) . . ?
C31 C32 H32 119.2 . . ?
C3 C33 H33 118.6 . . ?
C3 C33 C34 122.7(2) . . ?
C34 C33 H33 118.6 . . ?
N1 C34 C12 122.3(2) . . ?
N1 C34 C33 119.7(2) . . ?
C33 C34 C12 118.1(2) . . ?
N1 C35 C13 121.7(2) . . ?
N1 C35 C36 120.9(2) . . ?
C36 C35 C13 117.4(2) . . ?
C16 C36 C4 106.99(19) . . ?
C16 C36 C35 119.3(2) . . ?
C35 C36 C4 133.7(2) . . ?
C4 C37 H37 120.6 . . ?
C38 C37 C4 118.8(3) . . ?
C38 C37 H37 120.6 . . ?
C37 C38 H38 119.3 . . ?
C37 C38 C39 121.3(3) . . ?
C39 C38 H38 119.3 . . ?
C38 C39 H39 119.3 . . ?
C40 C39 C38 121.3(3) . . ?
C40 C39 H39 119.3 . . ?
C39 C40 H40 121.3 . . ?
C39 C40 C41 117.5(2) . . ?
C41 C40 H40 121.3 . . ?
N2 C41 C4 108.7(2) . . ?
C40 C41 N2 129.3(2) . . ?
C40 C41 C4 122.0(2) . . ?
C43 C42 C3 121.6(2) . . ?
C47 C42 C3 120.7(2) . . ?
C47 C42 C43 117.7(2) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 C42 120.7(2) . . ?
C44 C43 H43 119.7 . . ?
C43 C44 H44 119.4 . . ?
C43 C44 C45 121.3(3) . . ?
C45 C44 H44 119.4 . . ?
C44 C45 C46 118.7(2) . . ?
C44 C45 N48 121.3(3) . . ?
C46 C45 N48 120.0(3) . . ?
C45 C46 H46 120.1 . . ?
C47 C46 C45 119.8(3) . . ?
C47 C46 H46 120.1 . . ?
C42 C47 H47 119.1 . . ?
C46 C47 C42 121.8(2) . . ?
C46 C47 H47 119.1 . . ?
C49 N48 C45 119.0(3) . . ?
C55 N48 C45 119.9(3) . . ?
C55 N48 C49 121.0(2) . . ?
C50 C49 N48 121.0(4) . . ?
C54 C49 N48 119.6(3) . . ?
C54 C49 C50 119.3(4) . . ?
C49 C50 H50 119.9 . . ?
C51 C50 C49 120.2(5) . . ?
C51 C50 H50 119.9 . . ?
C50 C51 H51 119.8 . . ?
C52 C51 C50 120.4(5) . . ?
C52 C51 H51 119.8 . . ?
C51 C52 H52 119.6 . . ?
C51 C52 C53 120.8(5) . . ?
C53 C52 H52 119.6 . . ?
C52 C53 H53 120.3 . . ?
C52 C53 C54 119.3(6) . . ?
C54 C53 H53 120.3 . . ?
C49 C54 C53 119.9(5) . . ?
C49 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C56 C55 N48 121.1(3) . . ?
C56 C55 C60 118.6(3) . . ?
C60 C55 N48 120.3(3) . . ?
C55 C56 H56 119.0 . . ?
C55 C56 C57 121.9(4) . . ?
C57 C56 H56 119.0 . . ?
C56 C57 H57 120.4 . . ?
C58 C57 C56 119.2(4) . . ?
C58 C57 H57 120.4 . . ?
C57 C58 H58 120.1 . . ?
C59 C58 C57 119.7(4) . . ?
C59 C58 H58 120.1 . . ?
C58 C59 H59 119.3 . . ?
C58 C59 C60 121.4(4) . . ?
C60 C59 H59 119.3 . . ?
C55 C60 C59 119.1(4) . . ?
C55 C60 H60 120.5 . . ?
C59 C60 H60 120.5 . . ?

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
N1 C35 C36 C4 0.6(4) . . . . ?
N1 C35 C36 C16 -179.4(2) . . . . ?
N5 C12 C34 N1 2.2(4) . . . . ?
N5 C12 C34 C33 -177.9(2) . . . . ?
N5 C13 C14 C15 176.9(2) . . . . ?
N5 C13 C35 N1 2.2(4) . . . . ?
N5 C13 C35 C36 -177.8(2) . . . . ?
N2 C16 C36 C4 -0.1(3) . . . . ?
N2 C16 C36 C35 179.9(2) . . . . ?
N2 C17 C18 C19 -179.7(3) . . . . ?
N2 C17 C21 C22 -179.6(3) . . . . ?
C3 C10 C11 C12 -2.9(4) . . . . ?
C3 C33 C34 N1 175.9(2) . . . . ?
C3 C33 C34 C12 -4.0(3) . . . . ?
C3 C42 C43 C44 176.6(3) . . . . ?
C3 C42 C47 C46 -174.8(3) . . . . ?
C4 C37 C38 C39 1.2(4) . . . . ?
C1 C2 C61 C62 0.8(7) . . . . ?
C1 C23 C24 C62 -3.0(7) . . . . ?
C2 C1 C23 C24 2.8(10) . . . . ?
C2 C61 C62 N3 179.4(3) . . . . ?
C2 C61 C62 C24 -1.2(6) . . . . ?
C61 C62 N3 C6 -31.9(4) . . . . ?
C61 C62 N3 C25 151.3(3) . . . . ?
C61 C62 C24 C23 2.2(5) . . . . ?
C62 N3 C6 C7 134.2(3) . . . . ?
C62 N3 C6 C31 -48.6(4) . . . . ?
C62 N3 C25 C26 -42.4(5) . . . . ?
C62 N3 C25 C30 138.4(4) . . . . ?
N3 C62 C24 C23 -178.3(3) . . . . ?
N3 C6 C7 C8 175.1(3) . . . . ?
N3 C6 C31 C32 -176.3(3) . . . . ?
N3 C25 C26 C27 -178.7(4) . . . . ?
N3 C25 C30 C29 178.2(4) . . . . ?
C6 N3 C25 C26 140.8(4) . . . . ?
C6 N3 C25 C30 -38.3(5) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C6 C31 C32 C9 2.0(4) . . . . ?
C7 C6 C31 C32 1.0(4) . . . . ?
C7 C8 C9 C10 -178.0(3) . . . . ?
C7 C8 C9 C32 2.5(4) . . . . ?
C8 C9 C10 C3 47.6(3) . . . . ?
C8 C9 C10 C11 -131.8(3) . . . . ?
C8 C9 C32 C31 -3.7(4) . . . . ?
C9 C10 C11 C12 176.6(2) . . . . ?
C10 C3 C33 C34 0.7(3) . . . . ?
C10 C3 C42 C43 44.2(4) . . . . ?
C10 C3 C42 C47 -139.3(3) . . . . ?
C10 C9 C32 C31 176.8(2) . . . . ?
C10 C11 C12 N5 -178.8(2) . . . . ?
C10 C11 C12 C34 -0.4(4) . . . . ?
C11 C12 C34 N1 -176.1(2) . . . . ?
C11 C12 C34 C33 3.8(3) . . . . ?
C12 N5 C13 C14 -179.4(2) . . . . ?
C12 N5 C13 C35 1.0(3) . . . . ?
C13 N5 C12 C11 175.2(2) . . . . ?
C13 N5 C12 C34 -3.1(3) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C13 C35 C36 C4 -179.4(2) . . . . ?
C13 C35 C36 C16 0.6(3) . . . . ?
C14 C13 C35 N1 -177.4(2) . . . . ?
C14 C13 C35 C36 2.7(3) . . . . ?
C14 C15 C16 N2 178.9(2) . . . . ?
C14 C15 C16 C36 2.6(4) . . . . ?
C15 C16 C36 C4 176.7(2) . . . . ?
C15 C16 C36 C35 -3.4(3) . . . . ?
C16 N2 C17 C18 52.9(4) . . . . ?
C16 N2 C17 C21 -126.8(3) . . . . ?
C16 N2 C41 C4 0.5(3) . . . . ?
C16 N2 C41 C40 -177.4(3) . . . . ?
C17 N2 C16 C15 14.2(4) . . . . ?
C17 N2 C16 C36 -169.2(2) . . . . ?
C17 N2 C41 C4 169.3(2) . . . . ?
C17 N2 C41 C40 -8.6(4) . . . . ?
C17 C18 C19 C20 -1.1(5) . . . . ?
C17 C21 C22 C20 -0.5(5) . . . . ?
C18 C17 C21 C22 0.7(5) . . . . ?
C18 C19 C20 C22 1.3(6) . . . . ?
C19 C20 C22 C21 -0.5(6) . . . . ?
C21 C17 C18 C19 0.0(5) . . . . ?
C23 C1 C2 C61 -1.7(9) . . . . ?
C24 C62 N3 C6 148.6(3) . . . . ?
C24 C62 N3 C25 -28.1(5) . . . . ?
C25 N3 C6 C7 -48.9(4) . . . . ?
C25 N3 C6 C31 128.3(3) . . . . ?
C25 C26 C27 C28 -0.3(9) . . . . ?
C26 C25 C30 C29 -1.0(7) . . . . ?
C26 C27 C28 C29 0.6(10) . . . . ?
C27 C28 C29 C30 -1.1(10) . . . . ?
C28 C29 C30 C25 1.3(8) . . . . ?
C30 C25 C26 C27 0.5(7) . . . . ?
C31 C6 C7 C8 -2.2(4) . . . . ?
C32 C9 C10 C3 -132.9(3) . . . . ?
C32 C9 C10 C11 47.7(3) . . . . ?
C33 C3 C10 C9 -176.7(2) . . . . ?
C33 C3 C10 C11 2.8(3) . . . . ?
C33 C3 C42 C43 -133.6(3) . . . . ?
C33 C3 C42 C47 42.9(3) . . . . ?
C34 N1 C35 C13 -3.1(3) . . . . ?
C34 N1 C35 C36 176.9(2) . . . . ?
C35 N1 C34 C12 1.0(3) . . . . ?
C35 N1 C34 C33 -178.9(2) . . . . ?
C35 C13 C14 C15 -3.5(4) . . . . ?
C36 C4 C37 C38 -178.8(3) . . . . ?
C36 C4 C41 N2 -0.5(3) . . . . ?
C36 C4 C41 C40 177.6(2) . . . . ?
C37 C4 C36 C16 179.0(3) . . . . ?
C37 C4 C36 C35 -0.9(5) . . . . ?
C37 C4 C41 N2 -179.4(2) . . . . ?
C37 C4 C41 C40 -1.3(4) . . . . ?
C37 C38 C39 C40 -0.6(5) . . . . ?
C38 C39 C40 C41 -1.0(4) . . . . ?
C39 C40 C41 N2 179.6(3) . . . . ?
C39 C40 C41 C4 1.9(4) . . . . ?
C41 N2 C16 C15 -176.9(2) . . . . ?
C41 N2 C16 C36 -0.2(3) . . . . ?
C41 N2 C17 C18 -114.1(3) . . . . ?
C41 N2 C17 C21 66.2(4) . . . . ?
C41 C4 C36 C16 0.4(2) . . . . ?
C41 C4 C36 C35 -179.6(2) . . . . ?
C41 C4 C37 C38 -0.2(4) . . . . ?
C42 C3 C10 C9 5.6(3) . . . . ?
C42 C3 C10 C11 -175.0(2) . . . . ?
C42 C3 C33 C34 178.6(2) . . . . ?
C42 C43 C44 C45 -2.1(5) . . . . ?
C43 C42 C47 C46 1.9(4) . . . . ?
C43 C44 C45 C46 2.2(5) . . . . ?
C43 C44 C45 N48 -178.2(3) . . . . ?
C44 C45 C46 C47 -0.3(5) . . . . ?
C44 C45 N48 C49 -143.3(4) . . . . ?
C44 C45 N48 C55 37.0(5) . . . . ?
C45 C46 C47 C42 -1.7(5) . . . . ?
C45 N48 C49 C50 -128.1(4) . . . . ?
C45 N48 C49 C54 48.6(5) . . . . ?
C45 N48 C55 C56 36.1(5) . . . . ?
C45 N48 C55 C60 -143.5(3) . . . . ?
C46 C45 N48 C49 36.3(5) . . . . ?
C46 C45 N48 C55 -143.4(3) . . . . ?
C47 C42 C43 C44 0.0(4) . . . . ?
N48 C45 C46 C47 -180.0(3) . . . . ?
N48 C49 C50 C51 176.8(4) . . . . ?
N48 C49 C54 C53 -176.2(4) . . . . ?
N48 C55 C56 C57 -177.2(4) . . . . ?
N48 C55 C60 C59 177.9(3) . . . . ?
C49 N48 C55 C56 -143.6(4) . . . . ?
C49 N48 C55 C60 36.8(5) . . . . ?
C49 C50 C51 C52 -0.7(8) . . . . ?
C50 C49 C54 C53 0.6(6) . . . . ?
C50 C51 C52 C53 0.8(9) . . . . ?
C51 C52 C53 C54 -0.1(9) . . . . ?
C52 C53 C54 C49 -0.6(8) . . . . ?
C54 C49 C50 C51 0.0(6) . . . . ?
C55 N48 C49 C50 51.6(5) . . . . ?
C55 N48 C49 C54 -131.7(4) . . . . ?
C55 C56 C57 C58 -0.8(7) . . . . ?
C56 C55 C60 C59 -1.7(5) . . . . ?
C56 C57 C58 C59 -1.6(7) . . . . ?
C57 C58 C59 C60 2.3(6) . . . . ?
C58 C59 C60 C55 -0.7(6) . . . . ?
C60 C55 C56 C57 2.4(6) . . . . ?

_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 0.250 -0.173 0.250 361.5 20.5 ?
2 -0.250 0.173 0.750 361.5 20.5 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_zhx_4074_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2110952'
loop_
_audit_author_name
_audit_author_address
'zhang huaxing'
;sichuan university
China
;
_audit_update_record             
;
2021-09-21 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_audit_creation_date             2021-04-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H13 F2 N3'
_chemical_formula_sum            'C24 H13 F2 N3'
_chemical_formula_weight         381.37
_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'
F F 0.0171 0.0103 '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'

_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                   6.9727(12)
_cell_length_b                   21.106(2)
_cell_length_c                   13.7772(18)
_cell_angle_alpha                90
_cell_angle_beta                 120.245(3)
_cell_angle_gamma                90
_cell_volume                     1751.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4888
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.928
_cell_measurement_theta_min      2.579
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1304 before and 0.0674 after correction.
The Ratio of minimum to maximum transmission is 0.9148.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.43
_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  0.0744
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20872
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         1.930
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2345
_reflns_number_total             4010
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0106(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.024
_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)+(0.0494P)²+0.2887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1310
_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:
 C2(H2), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C13(H13), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_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
F1 F 1.1753(2) 0.31332(5) 0.77281(11) 0.0669(4) Uani 1 1 d . . . . .
F2 F 0.9055(2) 0.28339(5) 0.56107(12) 0.0660(4) Uani 1 1 d . . . . .
N1 N 0.9979(3) 0.53038(7) 0.69453(13) 0.0453(4) Uani 1 1 d . . . . .
N2 N 0.5341(3) 0.71082(7) 0.37359(13) 0.0414(4) Uani 1 1 d . . . . .
N3 N 0.7017(2) 0.49794(6) 0.46608(13) 0.0385(4) Uani 1 1 d . . . . .
C1 C 1.0628(3) 0.36124(9) 0.70154(18) 0.0479(5) Uani 1 1 d . . . . .
C2 C 1.0894(3) 0.42146(9) 0.73734(18) 0.0465(5) Uani 1 1 d . . . . .
H2 H 1.1854 0.4313 0.8125 0.056 Uiso 1 1 calc R U . . .
C3 C 0.9682(3) 0.46993(9) 0.65840(16) 0.0404(4) Uani 1 1 d . . . . .
C4 C 0.8831(3) 0.57460(8) 0.61694(16) 0.0396(4) Uani 1 1 d . . . . .
C5 C 0.9153(3) 0.63978(8) 0.65055(17) 0.0458(5) Uani 1 1 d . . . . .
H5 H 1.0129 0.6499 0.7254 0.055 Uiso 1 1 calc R U . . .
C6 C 0.8074(3) 0.68695(8) 0.57616(16) 0.0443(5) Uani 1 1 d . . . . .
H6 H 0.8308 0.7291 0.5989 0.053 Uiso 1 1 calc R U . . .
C7 C 0.6578(3) 0.67046(8) 0.46279(16) 0.0375(4) Uani 1 1 d . . . . .
C8 C 0.5387(3) 0.77869(8) 0.37690(16) 0.0411(5) Uani 1 1 d . . . . .
C9 C 0.6034(3) 0.81179(9) 0.31115(17) 0.0492(5) Uani 1 1 d . . . . .
H9 H 0.6454 0.7902 0.2660 0.059 Uiso 1 1 calc R U . . .
C10 C 0.6049(4) 0.87721(9) 0.31346(19) 0.0573(6) Uani 1 1 d . . . . .
H10 H 0.6474 0.8996 0.2692 0.069 Uiso 1 1 calc R U . . .
C11 C 0.5444(4) 0.90951(9) 0.38040(19) 0.0583(6) Uani 1 1 d . . . . .
H11 H 0.5445 0.9536 0.3810 0.070 Uiso 1 1 calc R U . . .
C12 C 0.9177(3) 0.34551(8) 0.58809(19) 0.0460(5) Uani 1 1 d . . . . .
C13 C 0.7990(3) 0.38919(8) 0.51108(18) 0.0444(5) Uani 1 1 d . . . . .
H13 H 0.7033 0.3776 0.4368 0.053 Uiso 1 1 calc R U . . .
C14 C 0.8207(3) 0.45368(8) 0.54404(16) 0.0382(4) Uani 1 1 d . . . . .
C15 C 0.7323(3) 0.55813(8) 0.50185(16) 0.0357(4) Uani 1 1 d . . . . .
C16 C 0.6172(3) 0.60835(8) 0.42507(15) 0.0359(4) Uani 1 1 d . . . . .
C17 C 0.4595(3) 0.60991(8) 0.30688(15) 0.0366(4) Uani 1 1 d . . . . .
C18 C 0.3521(3) 0.56377(9) 0.22407(17) 0.0445(5) Uani 1 1 d . . . . .
H18 H 0.3821 0.5210 0.2413 0.053 Uiso 1 1 calc R U . . .
C19 C 0.2018(3) 0.58270(9) 0.11688(18) 0.0527(5) Uani 1 1 d . . . . .
H19 H 0.1294 0.5523 0.0612 0.063 Uiso 1 1 calc R U . . .
C20 C 0.1553(4) 0.64665(10) 0.08966(18) 0.0548(6) Uani 1 1 d . . . . .
H20 H 0.0518 0.6581 0.0163 0.066 Uiso 1 1 calc R U . . .
C21 C 0.2597(3) 0.69310(9) 0.16919(17) 0.0475(5) Uani 1 1 d . . . . .
H21 H 0.2296 0.7358 0.1509 0.057 Uiso 1 1 calc R U . . .
C22 C 0.4115(3) 0.67412(8) 0.27772(16) 0.0395(4) Uani 1 1 d . . . . .
C23 C 0.4834(4) 0.87620(9) 0.44693(19) 0.0561(6) Uani 1 1 d . . . . .
H23 H 0.4450 0.8979 0.4934 0.067 Uiso 1 1 calc R U . . .
C24 C 0.4791(3) 0.81074(9) 0.44475(18) 0.0493(5) Uani 1 1 d . . . . .
H24 H 0.4361 0.7884 0.4889 0.059 Uiso 1 1 calc R U . . .


_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
F1 C1 1.351(2) . ?
F2 C12 1.354(2) . ?
N1 C3 1.347(2) . ?
N1 C4 1.339(2) . ?
N2 C7 1.383(2) . ?
N2 C8 1.433(2) . ?
N2 C22 1.392(2) . ?
N3 C14 1.348(2) . ?
N3 C15 1.340(2) . ?
C1 C2 1.342(3) . ?
C1 C12 1.409(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.421(3) . ?
C3 C14 1.423(3) . ?
C4 C5 1.433(2) . ?
C4 C15 1.436(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.353(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.417(3) . ?
C7 C16 1.386(2) . ?
C8 C9 1.387(3) . ?
C8 C24 1.377(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9300 . ?
C11 C23 1.382(3) . ?
C12 C13 1.333(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.419(2) . ?
C15 C16 1.425(2) . ?
C16 C17 1.434(3) . ?
C17 C18 1.397(2) . ?
C17 C22 1.405(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.371(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.395(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(3) . ?
C24 H24 0.9300 . ?

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
C4 N1 C3 116.51(16) . . ?
C7 N2 C8 126.40(16) . . ?
C7 N2 C22 108.09(14) . . ?
C22 N2 C8 125.42(16) . . ?
C15 N3 C14 116.35(16) . . ?
F1 C1 C12 117.36(17) . . ?
C2 C1 F1 121.3(2) . . ?
C2 C1 C12 121.34(18) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
N1 C3 C2 118.55(18) . . ?
N1 C3 C14 121.88(17) . . ?
C2 C3 C14 119.57(17) . . ?
N1 C4 C5 118.55(17) . . ?
N1 C4 C15 121.59(16) . . ?
C5 C4 C15 119.86(16) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.66(18) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C7 118.30(17) . . ?
C7 C6 H6 120.9 . . ?
N2 C7 C6 127.72(16) . . ?
N2 C7 C16 109.35(16) . . ?
C16 C7 C6 122.93(17) . . ?
C9 C8 N2 119.49(17) . . ?
C24 C8 N2 120.21(17) . . ?
C24 C8 C9 120.31(17) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.32(19) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C23 119.64(19) . . ?
C23 C11 H11 120.2 . . ?
F2 C12 C1 116.35(17) . . ?
C13 C12 F2 121.6(2) . . ?
C13 C12 C1 122.09(18) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.06(19) . . ?
C14 C13 H13 120.5 . . ?
N3 C14 C3 121.78(16) . . ?
N3 C14 C13 119.10(17) . . ?
C13 C14 C3 119.12(17) . . ?
N3 C15 C4 121.87(16) . . ?
N3 C15 C16 120.41(16) . . ?
C16 C15 C4 117.72(15) . . ?
C7 C16 C15 119.53(17) . . ?
C7 C16 C17 107.39(15) . . ?
C15 C16 C17 133.06(16) . . ?
C18 C17 C16 134.45(16) . . ?
C18 C17 C22 119.12(17) . . ?
C22 C17 C16 106.42(15) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.75(18) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.32(19) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 121.2 . . ?
C20 C21 C22 117.63(18) . . ?
C22 C21 H21 121.2 . . ?
N2 C22 C17 108.74(16) . . ?
C21 C22 N2 129.26(16) . . ?
C21 C22 C17 121.97(17) . . ?
C11 C23 H23 119.8 . . ?
C11 C23 C24 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
C8 C24 C23 119.69(19) . . ?
C8 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?

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
F1 C1 C2 C3 179.41(17) . . . . ?
F1 C1 C12 F2 -0.3(3) . . . . ?
F1 C1 C12 C13 179.98(17) . . . . ?
F2 C12 C13 C14 -179.19(16) . . . . ?
N1 C3 C14 N3 -0.5(3) . . . . ?
N1 C3 C14 C13 179.23(17) . . . . ?
N1 C4 C5 C6 178.96(18) . . . . ?
N1 C4 C15 N3 -1.1(3) . . . . ?
N1 C4 C15 C16 179.99(16) . . . . ?
N2 C7 C16 C15 178.00(15) . . . . ?
N2 C7 C16 C17 -0.4(2) . . . . ?
N2 C8 C9 C10 179.16(19) . . . . ?
N2 C8 C24 C23 -179.75(19) . . . . ?
N3 C15 C16 C7 -177.44(16) . . . . ?
N3 C15 C16 C17 0.5(3) . . . . ?
C1 C2 C3 N1 -179.12(17) . . . . ?
C1 C2 C3 C14 0.6(3) . . . . ?
C1 C12 C13 C14 0.6(3) . . . . ?
C2 C1 C12 F2 179.32(17) . . . . ?
C2 C1 C12 C13 -0.4(3) . . . . ?
C2 C3 C14 N3 179.80(17) . . . . ?
C2 C3 C14 C13 -0.5(3) . . . . ?
C3 N1 C4 C5 -177.73(16) . . . . ?
C3 N1 C4 C15 1.5(3) . . . . ?
C4 N1 C3 C2 178.94(17) . . . . ?
C4 N1 C3 C14 -0.8(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C4 C15 C16 C7 1.5(2) . . . . ?
C4 C15 C16 C17 179.43(18) . . . . ?
C5 C4 C15 N3 178.13(16) . . . . ?
C5 C4 C15 C16 -0.8(3) . . . . ?
C5 C6 C7 N2 -178.93(18) . . . . ?
C5 C6 C7 C16 0.1(3) . . . . ?
C6 C7 C16 C15 -1.2(3) . . . . ?
C6 C7 C16 C17 -179.63(17) . . . . ?
C7 N2 C8 C9 118.7(2) . . . . ?
C7 N2 C8 C24 -61.4(3) . . . . ?
C7 N2 C22 C17 -0.2(2) . . . . ?
C7 N2 C22 C21 178.09(19) . . . . ?
C7 C16 C17 C18 -178.37(19) . . . . ?
C7 C16 C17 C22 0.27(19) . . . . ?
C8 N2 C7 C6 2.7(3) . . . . ?
C8 N2 C7 C16 -176.49(16) . . . . ?
C8 N2 C22 C17 176.71(16) . . . . ?
C8 N2 C22 C21 -5.0(3) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C8 C24 C23 0.2(3) . . . . ?
C9 C10 C11 C23 0.6(3) . . . . ?
C10 C11 C23 C24 -1.2(3) . . . . ?
C11 C23 C24 C8 0.8(3) . . . . ?
C12 C1 C2 C3 -0.1(3) . . . . ?
C12 C13 C14 N3 179.64(17) . . . . ?
C12 C13 C14 C3 -0.1(3) . . . . ?
C14 N3 C15 C4 -0.2(2) . . . . ?
C14 N3 C15 C16 178.70(15) . . . . ?
C15 N3 C14 C3 0.9(2) . . . . ?
C15 N3 C14 C13 -178.79(15) . . . . ?
C15 C4 C5 C6 -0.3(3) . . . . ?
C15 C16 C17 C18 3.5(4) . . . . ?
C15 C16 C17 C22 -177.86(18) . . . . ?
C16 C17 C18 C19 178.01(19) . . . . ?
C16 C17 C22 N2 -0.02(19) . . . . ?
C16 C17 C22 C21 -178.50(18) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 C17 C22 N2 178.87(16) . . . . ?
C18 C17 C22 C21 0.4(3) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C20 C21 C22 N2 -178.01(19) . . . . ?
C20 C21 C22 C17 0.1(3) . . . . ?
C22 N2 C7 C6 179.57(18) . . . . ?
C22 N2 C7 C16 0.4(2) . . . . ?
C22 N2 C8 C9 -57.7(3) . . . . ?
C22 N2 C8 C24 122.2(2) . . . . ?
C22 C17 C18 C19 -0.5(3) . . . . ?
C24 C8 C9 C10 -0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_zhx-3710-150k
_database_code_depnum_ccdc_archive 'CCDC 2041455'
loop_
_audit_author_name
_audit_author_address
'zhang huaxing'
;sichuan university
China
;
_audit_update_record             
;
2020-10-30 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H15 N3'
_chemical_formula_sum            'C24 H15 N3'
_chemical_formula_weight         345.39
_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 0.0181 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                   3.91044(13)
_cell_length_b                   19.7705(8)
_cell_length_c                   21.0267(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1625.60(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2095
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      71.2160
_cell_measurement_theta_min      4.4750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5486
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.429
_diffrn_reflns_theta_min         4.205
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00  -6.00   1.00    1.00    --  -34.98 -77.00 150.00   98
  2  ω   -103.00 -16.00   1.00    1.00    --  -34.98 -57.00  60.00   87
  3  ω    -36.00  57.00   1.00    1.00    --   34.98 -38.00-150.00   93
  4  ω     13.00 106.00   1.00    1.00    --   34.98  38.00  30.00   93
  5  ω     87.00 177.00   1.00    1.59    --  106.90  45.00 -90.00   90
  6  ω    100.00 178.00   1.00    1.59    --  106.90 111.00 -30.00   78
  7  ω     37.00 110.00   1.00    1.59    --  106.90 -94.00  90.00   73
  8  ω     39.00 129.00   1.00    1.59    --  106.90 -30.00  60.00   90
  9  ω    140.00 178.00   1.00    1.59    --  106.90 111.00-180.00   38
 10  ω    106.00 134.00   1.00    1.59    --  106.90 111.00-180.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0196377000
_diffrn_orient_matrix_UB_12      0.0408497000
_diffrn_orient_matrix_UB_13      -0.0622912000
_diffrn_orient_matrix_UB_21      -0.0438004000
_diffrn_orient_matrix_UB_22      -0.0661251000
_diffrn_orient_matrix_UB_23      -0.0378646000
_diffrn_orient_matrix_UB_31      -0.3911149000
_diffrn_orient_matrix_UB_32      0.0053491000
_diffrn_orient_matrix_UB_33      0.0073166000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.511
_reflns_Friedel_fraction_full    0.806
_reflns_Friedel_fraction_max     0.766
_reflns_number_gt                2635
_reflns_number_total             2839
_reflns_odcompleteness_completeness 99.83
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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         0.255
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 809 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0601
_refine_ls_restrained_S_all      1.044
_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)+(0.1143P)²+0.0587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1637
_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:
 C005(H005), C008(H008), C00C(H00C), C00F(H00F), C00G(H00G), C00H(H00H),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R)
;
_atom_sites_solution_hydrogens   geom
_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
N001 N 0.0743(8) 0.53522(13) 0.36462(12) 0.0199(6) Uani 1 1 d . . . . .
N002 N 0.3483(7) 0.75584(13) 0.30304(11) 0.0187(6) Uani 1 1 d . . . . .
N003 N 0.3590(8) 0.55824(14) 0.48750(12) 0.0213(6) Uani 1 1 d . . . . .
C004 C 0.2010(8) 0.72154(16) 0.25173(13) 0.0179(7) Uani 1 1 d . . . . .
C005 C 0.2877(9) 0.86220(16) 0.36052(14) 0.0200(7) Uani 1 1 d . . . . .
H005 H 0.1642 0.8395 0.3917 0.024 Uiso 1 1 calc R . . . .
C006 C 0.1179(8) 0.65492(15) 0.27050(14) 0.0173(7) Uani 1 1 d . . . . .
C007 C 0.2296(8) 0.64890(15) 0.33577(13) 0.0169(7) Uani 1 1 d . . . . .
C008 C 0.3519(9) 0.93048(17) 0.36656(15) 0.0228(8) Uani 1 1 d . . . . .
H008 H 0.2783 0.9536 0.4026 0.027 Uiso 1 1 calc R . . . .
C009 C 0.2156(9) 0.59463(15) 0.38045(14) 0.0182(7) Uani 1 1 d . . . . .
C00A C 0.2086(9) 0.49865(16) 0.47208(15) 0.0200(7) Uani 1 1 d . . . . .
C00B C 0.3619(8) 0.60608(16) 0.44249(14) 0.0184(7) Uani 1 1 d . . . . .
C00C C -0.0377(9) 0.61109(16) 0.22764(15) 0.0207(7) Uani 1 1 d . . . . .
H00C H -0.0956 0.5673 0.2397 0.025 Uiso 1 1 calc R . . . .
C00D C 0.0665(9) 0.48739(16) 0.41038(15) 0.0206(7) Uani 1 1 d . . . . .
C00E C 0.3679(8) 0.71074(16) 0.35364(15) 0.0182(7) Uani 1 1 d . . . . .
C00F C 0.6344(9) 0.92998(17) 0.26540(16) 0.0240(7) Uani 1 1 d . . . . .
H00F H 0.7455 0.9531 0.2329 0.029 Uiso 1 1 calc R . . . .
C00G C 0.5792(8) 0.86174(16) 0.25980(14) 0.0196(7) Uani 1 1 d . . . . .
H00G H 0.6564 0.8387 0.2240 0.024 Uiso 1 1 calc R . . . .
C00H C 0.1316(8) 0.74484(16) 0.19019(14) 0.0200(7) Uani 1 1 d . . . . .
H00H H 0.1854 0.7887 0.1778 0.024 Uiso 1 1 calc R . . . .
C00I C 0.4088(9) 0.82722(16) 0.30738(14) 0.0186(7) Uani 1 1 d . . . . .
C00J C -0.0205(9) 0.69970(17) 0.14854(14) 0.0224(7) Uani 1 1 d . . . . .
H00J H -0.0682 0.7136 0.1072 0.027 Uiso 1 1 calc R . . . .
C00K C -0.1044(9) 0.63386(17) 0.16691(15) 0.0226(7) Uani 1 1 d . . . . .
H00K H -0.2069 0.6049 0.1377 0.027 Uiso 1 1 calc R . . . .
C00L C 0.5261(9) 0.96482(16) 0.31904(15) 0.0240(7) Uani 1 1 d . . . . .
H00L H 0.5699 1.0109 0.3231 0.029 Uiso 1 1 calc R . . . .
C00M C 0.5167(9) 0.66997(16) 0.45690(14) 0.0221(7) Uani 1 1 d . . . . .
H00M H 0.6180 0.6763 0.4965 0.027 Uiso 1 1 calc R . . . .
C00N C 0.5193(9) 0.72143(17) 0.41435(14) 0.0211(7) Uani 1 1 d . . . . .
H00N H 0.6179 0.7628 0.4246 0.025 Uiso 1 1 calc R . . . .
C00O C 0.1958(9) 0.44594(16) 0.51815(15) 0.0242(8) Uani 1 1 d . . . . .
H00O H 0.2887 0.4526 0.5584 0.029 Uiso 1 1 calc R . . . .
C00P C -0.0860(10) 0.42356(17) 0.39708(15) 0.0245(8) Uani 1 1 d . . . . .
H00P H -0.1803 0.4153 0.3572 0.029 Uiso 1 1 calc R . . . .
C00Q C -0.0941(10) 0.37453(16) 0.44276(16) 0.0270(8) Uani 1 1 d . . . . .
H00Q H -0.1949 0.3330 0.4337 0.032 Uiso 1 1 calc R . . . .
C00R C 0.0478(10) 0.38590(17) 0.50326(16) 0.0260(8) Uani 1 1 d . . . . .
H00R H 0.0401 0.3517 0.5336 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
N001 C009 1.340(4) . ?
N001 C00D 1.349(4) . ?
N002 C004 1.398(4) . ?
N002 C00E 1.390(4) . ?
N002 C00I 1.434(4) . ?
N003 C00A 1.356(4) . ?
N003 C00B 1.338(4) . ?
C004 C006 1.413(4) . ?
C004 C00H 1.400(4) . ?
C005 H005 0.9300 . ?
C005 C008 1.379(4) . ?
C005 C00I 1.397(4) . ?
C006 C007 1.445(4) . ?
C006 C00C 1.390(4) . ?
C007 C009 1.427(4) . ?
C007 C00E 1.389(4) . ?
C008 H008 0.9300 . ?
C008 C00L 1.387(5) . ?
C009 C00B 1.442(4) . ?
C00A C00D 1.429(4) . ?
C00A C00O 1.424(4) . ?
C00B C00M 1.433(4) . ?
C00C H00C 0.9300 . ?
C00C C00K 1.379(4) . ?
C00D C00P 1.424(5) . ?
C00E C00N 1.423(4) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.371(4) . ?
C00F C00L 1.388(4) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.382(4) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.385(4) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.397(5) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.355(4) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00O C00R 1.357(5) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.365(4) . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.406(5) . ?
C00R H00R 0.9300 . ?

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
C009 N001 C00D 116.5(3) . . ?
C004 N002 C00I 126.5(2) . . ?
C00E N002 C004 107.6(2) . . ?
C00E N002 C00I 125.0(2) . . ?
C00B N003 C00A 116.7(3) . . ?
N002 C004 C006 109.3(3) . . ?
N002 C004 C00H 129.3(3) . . ?
C00H C004 C006 121.4(3) . . ?
C008 C005 H005 120.1 . . ?
C008 C005 C00I 119.8(3) . . ?
C00I C005 H005 120.1 . . ?
C004 C006 C007 105.8(3) . . ?
C00C C006 C004 120.0(3) . . ?
C00C C006 C007 134.1(3) . . ?
C009 C007 C006 132.5(3) . . ?
C00E C007 C006 107.6(3) . . ?
C00E C007 C009 119.9(3) . . ?
C005 C008 H008 119.9 . . ?
C005 C008 C00L 120.2(3) . . ?
C00L C008 H008 119.9 . . ?
N001 C009 C007 120.8(3) . . ?
N001 C009 C00B 121.7(3) . . ?
C007 C009 C00B 117.5(3) . . ?
N003 C00A C00D 121.4(3) . . ?
N003 C00A C00O 119.2(3) . . ?
C00O C00A C00D 119.3(3) . . ?
N003 C00B C009 121.7(3) . . ?
N003 C00B C00M 118.5(3) . . ?
C00M C00B C009 119.8(3) . . ?
C006 C00C H00C 120.7 . . ?
C00K C00C C006 118.7(3) . . ?
C00K C00C H00C 120.7 . . ?
N001 C00D C00A 122.0(3) . . ?
N001 C00D C00P 119.4(3) . . ?
C00P C00D C00A 118.7(3) . . ?
N002 C00E C00N 127.9(3) . . ?
C007 C00E N002 109.6(3) . . ?
C007 C00E C00N 122.4(3) . . ?
C00G C00F H00F 119.7 . . ?
C00G C00F C00L 120.7(3) . . ?
C00L C00F H00F 119.7 . . ?
C00F C00G H00G 120.0 . . ?
C00F C00G C00I 120.0(3) . . ?
C00I C00G H00G 120.0 . . ?
C004 C00H H00H 121.4 . . ?
C00J C00H C004 117.1(3) . . ?
C00J C00H H00H 121.4 . . ?
C005 C00I N002 118.8(3) . . ?
C00G C00I N002 121.3(3) . . ?
C00G C00I C005 119.9(3) . . ?
C00H C00J H00J 119.1 . . ?
C00H C00J C00K 121.8(3) . . ?
C00K C00J H00J 119.1 . . ?
C00C C00K C00J 121.1(3) . . ?
C00C C00K H00K 119.5 . . ?
C00J C00K H00K 119.5 . . ?
C008 C00L C00F 119.5(3) . . ?
C008 C00L H00L 120.2 . . ?
C00F C00L H00L 120.2 . . ?
C00B C00M H00M 119.2 . . ?
C00N C00M C00B 121.7(3) . . ?
C00N C00M H00M 119.2 . . ?
C00E C00N H00N 120.7 . . ?
C00M C00N C00E 118.5(3) . . ?
C00M C00N H00N 120.7 . . ?
C00A C00O H00O 120.1 . . ?
C00R C00O C00A 119.9(3) . . ?
C00R C00O H00O 120.1 . . ?
C00D C00P H00P 120.0 . . ?
C00Q C00P C00D 120.1(3) . . ?
C00Q C00P H00P 120.0 . . ?
C00P C00Q H00Q 119.5 . . ?
C00P C00Q C00R 120.9(3) . . ?
C00R C00Q H00Q 119.5 . . ?
C00O C00R C00Q 121.1(3) . . ?
C00O C00R H00R 119.4 . . ?
C00Q C00R H00R 119.4 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-10-27
_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 1.442
_oxdiff_exptl_absorpt_empirical_full_min 0.725
####################################################################### 
# 
# 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_zhx-no2
_database_code_depnum_ccdc_archive 'CCDC 2041452'
loop_
_audit_author_name
_audit_author_address
'zhang huaxing'
;sichuan university
China
;
_audit_update_record             
;
2020-10-30 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_audit_creation_date             2020-09-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H7 N3 O2'
_chemical_formula_sum            'C12 H7 N3 O2'
_chemical_formula_weight         225.21
_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'
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           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                   6.8370(4)
_cell_length_b                   22.4145(11)
_cell_length_c                   7.1605(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.235(7)
_cell_angle_gamma                90
_cell_volume                     1000.63(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1588
_cell_measurement_temperature    296.4(8)
_cell_measurement_theta_max      70.4490
_cell_measurement_theta_min      5.7320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5414
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.269
_diffrn_reflns_theta_min         3.944
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.4(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  33.00   1.00    4.49    --  -34.98  57.00  30.00   86
  2  ω    -34.00  64.00   1.00    4.49    --   34.98 -77.00-150.00   98
  3  ω     16.00 103.00   1.00    4.49    --   34.98  57.00  60.00   87
  4  ω    -34.00  64.00   1.00    4.49    --   34.98 -77.00 -60.00   98
  5  ω      1.00  75.00   1.00    4.49    --   34.98 -99.00  90.00   74
  6  ω    100.00 178.00   1.00   17.97    --  106.90 111.00-120.00   78
  7  ω     78.00 176.00   1.00   17.97    --  106.90  77.00-120.00   98
  8  ω    100.00 178.00   1.00   17.97    --  106.90 111.00 -30.00   78
  9  ω     61.00 178.00   1.00   17.97    --  106.90  15.00 -60.00  117
 10  ω    100.00 178.00   1.00   17.97    --  106.90 111.00 120.00   78
 11  ω     36.00 113.00   1.00   17.97    --  106.90-111.00-180.00   77
 12  ω     37.00 110.00   1.00   17.97    --  106.90 -94.00  30.00   73
 13  ω    100.00 178.00   1.00   17.97    --  106.90 111.00   0.00   78
 14  ω   -103.00 -16.00   1.00    4.49    --  -34.98 -57.00-120.00   87
 15  ω     16.00 103.00   1.00    4.49    --   34.98  57.00 150.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0233045000
_diffrn_orient_matrix_UB_12      -0.0668973000
_diffrn_orient_matrix_UB_13      -0.0541163000
_diffrn_orient_matrix_UB_21      0.1568401000
_diffrn_orient_matrix_UB_22      0.0070730000
_diffrn_orient_matrix_UB_23      -0.1034164000
_diffrn_orient_matrix_UB_31      0.1895876000
_diffrn_orient_matrix_UB_32      -0.0140289000
_diffrn_orient_matrix_UB_33      0.2049786000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1510
_reflns_number_total             1917
_reflns_odcompleteness_completeness 99.84
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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         0.320
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0702
_refine_ls_restrained_S_all      1.100
_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)+(0.1413P)²+0.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2204
_refine_ls_wR_factor_ref         0.2332
_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:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H)
;
_atom_sites_solution_hydrogens   geom
_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
N001 N 0.9247(2) 0.47964(8) 0.7127(2) 0.0396(5) Uani 1 1 d . . . . .
N002 N 0.5743(2) 0.52263(8) 0.7907(2) 0.0408(5) Uani 1 1 d . . . . .
O003 O 0.4510(4) 0.25353(9) 0.5568(4) 0.0865(7) Uani 1 1 d . . . . .
C004 C 0.5869(3) 0.46547(9) 0.7429(3) 0.0386(5) Uani 1 1 d . . . . .
C005 C 0.9124(3) 0.53681(9) 0.7609(3) 0.0377(5) Uani 1 1 d . . . . .
C006 C 0.7357(3) 0.55853(9) 0.8008(3) 0.0387(5) Uani 1 1 d . . . . .
C007 C 0.7626(3) 0.44414(9) 0.7019(3) 0.0380(5) Uani 1 1 d . . . . .
O008 O 0.7482(4) 0.26895(9) 0.5288(4) 0.0909(8) Uani 1 1 d . . . . .
N009 N 0.6010(4) 0.28545(9) 0.5702(3) 0.0617(6) Uani 1 1 d . . . . .
C00A C 0.6009(3) 0.34757(9) 0.6364(3) 0.0464(6) Uani 1 1 d . . . . .
C00B C 0.7651(3) 0.38330(10) 0.6466(3) 0.0435(5) Uani 1 1 d . . . . .
H00B H 0.8767 0.3684 0.6181 0.052 Uiso 1 1 calc R . . . .
C00C C 0.7320(3) 0.61970(10) 0.8514(3) 0.0462(6) Uani 1 1 d . . . . .
H00C H 0.6192 0.6344 0.8785 0.055 Uiso 1 1 calc R . . . .
C00D C 0.4291(3) 0.36720(10) 0.6798(3) 0.0498(6) Uani 1 1 d . . . . .
H00D H 0.3220 0.3407 0.6739 0.060 Uiso 1 1 calc R . . . .
C00E C 1.0782(3) 0.57705(10) 0.7726(3) 0.0451(5) Uani 1 1 d . . . . .
H00E H 1.1943 0.5635 0.7484 0.054 Uiso 1 1 calc R . . . .
C00F C 0.4207(3) 0.42496(10) 0.7303(3) 0.0462(6) Uani 1 1 d . . . . .
H00F H 0.3061 0.4384 0.7571 0.055 Uiso 1 1 calc R . . . .
C00G C 1.0665(3) 0.63510(10) 0.8190(4) 0.0508(6) Uani 1 1 d . . . . .
H00G H 1.1739 0.6613 0.8242 0.061 Uiso 1 1 calc R . . . .
C00H C 0.8922(4) 0.65667(10) 0.8602(3) 0.0515(6) Uani 1 1 d . . . . .
H00H H 0.8884 0.6966 0.8935 0.062 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
N001 C005 1.338(3) . ?
N001 C007 1.340(3) . ?
N002 C004 1.338(3) . ?
N002 C006 1.343(3) . ?
O003 N009 1.221(3) . ?
C004 C007 1.431(3) . ?
C004 C00F 1.428(3) . ?
C005 C006 1.436(3) . ?
C005 C00E 1.424(3) . ?
C006 C00C 1.421(3) . ?
C007 C00B 1.422(3) . ?
O008 N009 1.217(3) . ?
N009 C00A 1.471(3) . ?
C00A C00B 1.356(3) . ?
C00A C00D 1.403(3) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00H 1.354(3) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.352(3) . ?
C00E H00E 0.9300 . ?
C00E C00G 1.353(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00H 1.424(3) . ?
C00H H00H 0.9300 . ?

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
C005 N001 C007 116.45(17) . . ?
C004 N002 C006 116.74(17) . . ?
N002 C004 C007 121.32(19) . . ?
N002 C004 C00F 119.47(18) . . ?
C00F C004 C007 119.2(2) . . ?
N001 C005 C006 121.52(19) . . ?
N001 C005 C00E 119.28(18) . . ?
C00E C005 C006 119.20(19) . . ?
N002 C006 C005 121.71(19) . . ?
N002 C006 C00C 119.46(18) . . ?
C00C C006 C005 118.83(19) . . ?
N001 C007 C004 122.26(19) . . ?
N001 C007 C00B 118.78(18) . . ?
C00B C007 C004 118.96(19) . . ?
O003 N009 C00A 117.9(2) . . ?
O008 N009 O003 123.7(2) . . ?
O008 N009 C00A 118.4(2) . . ?
C00B C00A N009 117.8(2) . . ?
C00B C00A C00D 123.5(2) . . ?
C00D C00A N009 118.6(2) . . ?
C007 C00B H00B 120.7 . . ?
C00A C00B C007 118.52(19) . . ?
C00A C00B H00B 120.7 . . ?
C006 C00C H00C 119.9 . . ?
C00H C00C C006 120.26(19) . . ?
C00H C00C H00C 119.9 . . ?
C00A C00D H00D 120.3 . . ?
C00F C00D C00A 119.4(2) . . ?
C00F C00D H00D 120.3 . . ?
C005 C00E H00E 120.1 . . ?
C00G C00E C005 119.81(19) . . ?
C00G C00E H00E 120.1 . . ?
C004 C00F H00F 119.8 . . ?
C00D C00F C004 120.4(2) . . ?
C00D C00F H00F 119.8 . . ?
C00E C00G H00G 119.5 . . ?
C00E C00G C00H 121.1(2) . . ?
C00H C00G H00G 119.5 . . ?
C00C C00H C00G 120.8(2) . . ?
C00C C00H H00H 119.6 . . ?
C00G C00H H00H 119.6 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-09-08
_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 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.520
