# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_9111
_database_code_depnum_ccdc_archive 'CCDC 2073464'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;School of Chemistry and Environment,South China Normal University
China
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 N2'
_chemical_formula_sum            'C18 H14 N2'
_chemical_formula_weight         258.31
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.6034(8)
_cell_length_b                   12.7690(11)
_cell_length_c                   10.6190(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.867(9)
_cell_angle_gamma                90
_cell_volume                     1343.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1430
_cell_measurement_temperature    297
_cell_measurement_theta_max      22.7740
_cell_measurement_theta_min      3.8010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6242
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.384
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  13.00   1.00    7.50    --   15.49 -38.00 -30.00   64
  2  ω    -25.00  16.00   1.00    7.50    --  -16.28 -99.00 120.00   41
  3  ω    -85.00   2.00   1.00    7.50    --  -16.28 -38.00-120.00   87
  4  ω    -21.00  22.00   1.00    7.50    --  -16.28 -99.00-120.00   43
  5  ω    -63.00 -30.00   1.00    7.50    --  -16.28 -57.00  90.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0311066000
_diffrn_orient_matrix_UB_12      0.0490277000
_diffrn_orient_matrix_UB_13      0.0228924000
_diffrn_orient_matrix_UB_21      -0.0011333000
_diffrn_orient_matrix_UB_22      0.0113250000
_diffrn_orient_matrix_UB_23      -0.0658061000
_diffrn_orient_matrix_UB_31      -0.0644863000
_diffrn_orient_matrix_UB_32      0.0234525000
_diffrn_orient_matrix_UB_33      -0.0160529000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1571
_reflns_number_total             2366
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.061
_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)+(0.0489P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1372
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C14(H14),
 C15(H15), C18(H18)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 0.60967(16) 0.60754(15) 0.44385(17) 0.0391(5) Uani 1 1 d . . . . .
N2 N 0.38079(17) 0.60421(16) 0.35289(17) 0.0453(5) Uani 1 1 d . . . . .
C1 C 0.5631(2) 0.67310(18) 0.5226(2) 0.0371(6) Uani 1 1 d . . . . .
C2 C 1.0585(3) 0.7191(2) 0.6549(4) 0.0742(9) Uani 1 1 d . . . . .
H2 H 1.117391 0.768767 0.642979 0.089 Uiso 1 1 calc R U . . .
C3 C 0.9962(2) 0.6032(2) 0.7974(3) 0.0636(8) Uani 1 1 d . . . . .
H3 H 1.013356 0.573584 0.881940 0.076 Uiso 1 1 calc R U . . .
C4 C 0.4223(2) 0.66851(19) 0.4643(2) 0.0393(6) Uani 1 1 d . . . . .
C5 C 0.7490(2) 0.5222(2) 0.3490(3) 0.0571(7) Uani 1 1 d . . . . .
H5 H 0.834418 0.505647 0.348984 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4937(2) 0.56947(19) 0.3413(2) 0.0406(6) Uani 1 1 d . . . . .
C7 C 0.9458(2) 0.6897(2) 0.5475(3) 0.0627(8) Uani 1 1 d . . . . .
H7 H 0.929547 0.718951 0.462962 0.075 Uiso 1 1 calc R U . . .
C8 C 0.6271(2) 0.73972(19) 0.6295(2) 0.0458(6) Uani 1 1 d . . . . .
H8 H 0.720753 0.744142 0.666356 0.055 Uiso 1 1 calc R U . . .
C9 C 0.8829(2) 0.5746(2) 0.6905(2) 0.0530(7) Uani 1 1 d . . . . .
H9 H 0.823253 0.526124 0.703609 0.064 Uiso 1 1 calc R U . . .
C10 C 0.7386(2) 0.58141(19) 0.4492(2) 0.0444(6) Uani 1 1 d . . . . .
C11 C 0.4068(2) 0.7926(2) 0.6235(2) 0.0566(7) Uani 1 1 d . . . . .
H11 H 0.355288 0.833057 0.659937 0.068 Uiso 1 1 calc R U . . .
C12 C 0.8568(2) 0.6167(2) 0.5647(2) 0.0450(6) Uani 1 1 d . . . . .
C13 C 0.6342(3) 0.4842(2) 0.2432(2) 0.0596(7) Uani 1 1 d . . . . .
H13 H 0.646007 0.443029 0.176050 0.072 Uiso 1 1 calc R U . . .
C14 C 0.5468(2) 0.7989(2) 0.6786(2) 0.0532(7) Uani 1 1 d . . . . .
H14 H 0.586990 0.844195 0.750350 0.064 Uiso 1 1 calc R U . . .
C15 C 1.0838(3) 0.6754(3) 0.7791(4) 0.0705(9) Uani 1 1 d . . . . .
H15 H 1.160528 0.694616 0.851136 0.085 Uiso 1 1 calc R U . . .
C16 C 0.5079(2) 0.5065(2) 0.2378(2) 0.0478(6) Uani 1 1 d . . . . .
C17 C 0.3823(3) 0.4694(2) 0.1271(2) 0.0693(9) Uani 1 1 d . . . . .
H17A H 0.336366 0.419367 0.162836 0.104 Uiso 1 1 calc R U . . .
H17B H 0.406521 0.437206 0.057216 0.104 Uiso 1 1 calc R U . . .
H17C H 0.323985 0.528008 0.090647 0.104 Uiso 1 1 calc R U . . .
C18 C 0.3432(2) 0.7279(2) 0.5164(2) 0.0521(7) Uani 1 1 d . . . . .
H18 H 0.249550 0.723981 0.479943 0.063 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 C1 1.392(3) . ?
N1 C6 1.407(3) . ?
N1 C10 1.389(3) . ?
N2 C4 1.377(3) . ?
N2 C6 1.323(3) . ?
C1 C4 1.399(3) . ?
C1 C8 1.387(3) . ?
C2 H2 0.9300 . ?
C2 C7 1.378(3) . ?
C2 C15 1.367(4) . ?
C3 H3 0.9300 . ?
C3 C9 1.376(3) . ?
C3 C15 1.371(4) . ?
C4 C18 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C10 1.341(3) . ?
C5 C13 1.416(3) . ?
C6 C16 1.412(3) . ?
C7 H7 0.9300 . ?
C7 C12 1.384(3) . ?
C8 H8 0.9300 . ?
C8 C14 1.373(3) . ?
C9 H9 0.9300 . ?
C9 C12 1.374(3) . ?
C10 C12 1.478(3) . ?
C11 H11 0.9300 . ?
C11 C14 1.391(3) . ?
C11 C18 1.373(3) . ?
C13 H13 0.9300 . ?
C13 C16 1.350(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.505(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18 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
C1 N1 C6 105.87(16) . . ?
C10 N1 C1 132.43(18) . . ?
C10 N1 C6 121.6(2) . . ?
C6 N2 C4 104.89(17) . . ?
N1 C1 C4 105.04(18) . . ?
C8 C1 N1 133.27(19) . . ?
C8 C1 C4 121.5(2) . . ?
C7 C2 H2 120.0 . . ?
C15 C2 H2 120.0 . . ?
C15 C2 C7 120.1(3) . . ?
C9 C3 H3 120.1 . . ?
C15 C3 H3 120.1 . . ?
C15 C3 C9 119.8(3) . . ?
N2 C4 C1 111.69(19) . . ?
N2 C4 C18 128.1(2) . . ?
C18 C4 C1 120.2(2) . . ?
C10 C5 H5 118.9 . . ?
C10 C5 C13 122.1(2) . . ?
C13 C5 H5 118.9 . . ?
N1 C6 C16 119.5(2) . . ?
N2 C6 N1 112.5(2) . . ?
N2 C6 C16 127.9(2) . . ?
C2 C7 H7 119.8 . . ?
C2 C7 C12 120.3(3) . . ?
C12 C7 H7 119.8 . . ?
C1 C8 H8 121.3 . . ?
C14 C8 C1 117.4(2) . . ?
C14 C8 H8 121.3 . . ?
C3 C9 H9 119.6 . . ?
C12 C9 C3 120.8(2) . . ?
C12 C9 H9 119.6 . . ?
N1 C10 C12 119.4(2) . . ?
C5 C10 N1 117.5(2) . . ?
C5 C10 C12 123.1(2) . . ?
C14 C11 H11 119.4 . . ?
C18 C11 H11 119.4 . . ?
C18 C11 C14 121.2(2) . . ?
C7 C12 C10 120.8(2) . . ?
C9 C12 C7 118.8(2) . . ?
C9 C12 C10 120.4(2) . . ?
C5 C13 H13 119.3 . . ?
C16 C13 C5 121.4(2) . . ?
C16 C13 H13 119.3 . . ?
C8 C14 C11 121.5(2) . . ?
C8 C14 H14 119.3 . . ?
C11 C14 H14 119.3 . . ?
C2 C15 C3 120.1(3) . . ?
C2 C15 H15 119.9 . . ?
C3 C15 H15 119.9 . . ?
C6 C16 C17 118.5(2) . . ?
C13 C16 C6 117.8(2) . . ?
C13 C16 C17 123.7(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18 120.9 . . ?
C11 C18 C4 118.2(2) . . ?
C11 C18 H18 120.9 . . ?

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 C1 C4 N2 -0.6(2) . . . . ?
N1 C1 C4 C18 -178.2(2) . . . . ?
N1 C1 C8 C14 175.8(2) . . . . ?
N1 C6 C16 C13 0.9(3) . . . . ?
N1 C6 C16 C17 -178.2(2) . . . . ?
N1 C10 C12 C7 -112.8(3) . . . . ?
N1 C10 C12 C9 69.7(3) . . . . ?
N2 C4 C18 C11 -175.4(2) . . . . ?
N2 C6 C16 C13 177.0(2) . . . . ?
N2 C6 C16 C17 -2.2(4) . . . . ?
C1 N1 C6 N2 -1.5(2) . . . . ?
C1 N1 C6 C16 175.1(2) . . . . ?
C1 N1 C10 C5 -173.9(2) . . . . ?
C1 N1 C10 C12 7.7(4) . . . . ?
C1 C4 C18 C11 1.7(3) . . . . ?
C1 C8 C14 C11 -0.1(4) . . . . ?
C2 C7 C12 C9 0.0(4) . . . . ?
C2 C7 C12 C10 -177.5(2) . . . . ?
C3 C9 C12 C7 -0.7(4) . . . . ?
C3 C9 C12 C10 176.8(2) . . . . ?
C4 N2 C6 N1 1.1(3) . . . . ?
C4 N2 C6 C16 -175.2(2) . . . . ?
C4 C1 C8 C14 1.9(3) . . . . ?
C5 C10 C12 C7 69.0(3) . . . . ?
C5 C10 C12 C9 -108.5(3) . . . . ?
C5 C13 C16 C6 0.1(4) . . . . ?
C5 C13 C16 C17 179.2(2) . . . . ?
C6 N1 C1 C4 1.2(2) . . . . ?
C6 N1 C1 C8 -173.4(2) . . . . ?
C6 N1 C10 C5 3.1(3) . . . . ?
C6 N1 C10 C12 -175.3(2) . . . . ?
C6 N2 C4 C1 -0.3(3) . . . . ?
C6 N2 C4 C18 177.0(2) . . . . ?
C7 C2 C15 C3 -0.9(4) . . . . ?
C8 C1 C4 N2 174.8(2) . . . . ?
C8 C1 C4 C18 -2.8(3) . . . . ?
C9 C3 C15 C2 0.2(4) . . . . ?
C10 N1 C1 C4 178.6(2) . . . . ?
C10 N1 C1 C8 4.0(4) . . . . ?
C10 N1 C6 N2 -179.22(19) . . . . ?
C10 N1 C6 C16 -2.6(3) . . . . ?
C10 C5 C13 C16 0.4(4) . . . . ?
C13 C5 C10 N1 -2.0(4) . . . . ?
C13 C5 C10 C12 176.3(2) . . . . ?
C14 C11 C18 C4 0.0(4) . . . . ?
C15 C2 C7 C12 0.8(4) . . . . ?
C15 C3 C9 C12 0.7(4) . . . . ?
C18 C11 C14 C8 -0.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.810
####################################################################### 
# 
# 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_exp_8359
_database_code_depnum_ccdc_archive 'CCDC 2073471'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;School of Chemistry and Environment,South China Normal University
China
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_audit_creation_date             2021-01-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 Cl N2'
_chemical_formula_sum            'C23 H15 Cl N2'
_chemical_formula_weight         354.82
_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'
Cl Cl 0.1484 0.1585 '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      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                   9.8768(10)
_cell_length_b                   9.9849(14)
_cell_length_c                   10.2735(14)
_cell_angle_alpha                106.386(12)
_cell_angle_beta                 91.697(10)
_cell_angle_gamma                116.134(12)
_cell_volume                     858.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1534
_cell_measurement_temperature    297
_cell_measurement_theta_max      25.1610
_cell_measurement_theta_min      3.9550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7162
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.408
_diffrn_reflns_theta_min         3.679
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  80.00   1.00    1.32    --   15.65  77.00 -90.00   89
  2  ω     24.00  50.00   1.00    1.32    --  -16.28  37.00-180.00   26
  3  ω    -21.00  21.00   1.00    1.32    --  -16.28 -99.00 -60.00   42
  4  ω    -12.00  20.00   1.00    1.32    --  -16.28 -99.00  30.00   32
  5  ω    -52.00  42.00   1.00    1.32    --   15.65 -77.00 150.00   94
  6  ω    -86.00 -26.00   1.00    1.32    --  -16.28 -37.00   0.00   60
  7  ω     35.00  65.00   1.00    1.32    --   15.65 178.00 150.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0699745000
_diffrn_orient_matrix_UB_12      0.0092269000
_diffrn_orient_matrix_UB_13      -0.0221742000
_diffrn_orient_matrix_UB_21      -0.0389306000
_diffrn_orient_matrix_UB_22      -0.0768811000
_diffrn_orient_matrix_UB_23      -0.0493668000
_diffrn_orient_matrix_UB_31      -0.0140670000
_diffrn_orient_matrix_UB_32      0.0320117000
_diffrn_orient_matrix_UB_33      -0.0492029000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2349
_reflns_number_total             3948
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.021
_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)+(0.0430P)²+0.1436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1296
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
Cl1 Cl 1.14694(9) 0.27551(12) 1.23176(7) 0.1091(4) Uani 1 1 d . . . . .
N1 N 0.63630(18) 0.23478(18) 0.56238(15) 0.0411(4) Uani 1 1 d . . . . .
N2 N 0.59795(18) 0.1956(2) 0.76849(16) 0.0456(4) Uani 1 1 d . . . . .
C1 C 0.6991(2) 0.2313(2) 0.68588(19) 0.0413(5) Uani 1 1 d . . . . .
C2 C 0.8559(2) 0.2666(2) 0.7073(2) 0.0463(5) Uani 1 1 d . . . . .
C3 C 0.9370(3) 0.3020(3) 0.6059(2) 0.0575(6) Uani 1 1 d . . . . .
H3 H 1.038990 0.323082 0.616499 0.069 Uiso 1 1 calc R U . . .
C4 C 0.8702(3) 0.3074(3) 0.4852(2) 0.0599(6) Uani 1 1 d . . . . .
H4 H 0.929536 0.331801 0.418450 0.072 Uiso 1 1 calc R U . . .
C5 C 0.7232(3) 0.2784(2) 0.4638(2) 0.0479(5) Uani 1 1 d . . . . .
C6 C 0.4818(2) 0.1929(2) 0.56927(19) 0.0414(5) Uani 1 1 d . . . . .
C7 C 0.3598(3) 0.1691(2) 0.4789(2) 0.0523(5) Uani 1 1 d . . . . .
H7 H 0.370728 0.178439 0.391763 0.063 Uiso 1 1 calc R U . . .
C8 C 0.2228(3) 0.1315(3) 0.5237(2) 0.0596(6) Uani 1 1 d . . . . .
H8 H 0.138944 0.114809 0.465347 0.072 Uiso 1 1 calc R U . . .
C9 C 0.2048(3) 0.1173(3) 0.6542(2) 0.0595(6) Uani 1 1 d . . . . .
H9 H 0.110649 0.094702 0.682077 0.071 Uiso 1 1 calc R U . . .
C10 C 0.3233(2) 0.1361(3) 0.7414(2) 0.0517(5) Uani 1 1 d . . . . .
H10 H 0.310325 0.124466 0.827544 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4648(2) 0.1732(2) 0.69860(19) 0.0429(5) Uani 1 1 d . . . . .
C12 C 0.9263(2) 0.2660(3) 0.8363(2) 0.0477(5) Uani 1 1 d . . . . .
C13 C 0.8528(3) 0.1478(3) 0.8926(2) 0.0605(6) Uani 1 1 d . . . . .
H13 H 0.755401 0.066467 0.849487 0.073 Uiso 1 1 calc R U . . .
C14 C 0.9220(3) 0.1488(3) 1.0120(3) 0.0723(7) Uani 1 1 d . . . . .
H14 H 0.872480 0.067218 1.047637 0.087 Uiso 1 1 calc R U . . .
C15 C 1.0639(3) 0.2706(3) 1.0777(2) 0.0667(7) Uani 1 1 d . . . . .
C16 C 1.1406(3) 0.3880(3) 1.0236(2) 0.0668(7) Uani 1 1 d . . . . .
H16 H 1.237973 0.468845 1.067333 0.080 Uiso 1 1 calc R U . . .
C17 C 1.0716(3) 0.3850(3) 0.9031(2) 0.0594(6) Uani 1 1 d . . . . .
H17 H 1.123788 0.464681 0.866007 0.071 Uiso 1 1 calc R U . . .
C18 C 0.6550(2) 0.3006(2) 0.3464(2) 0.0481(5) Uani 1 1 d . . . . .
C19 C 0.6312(3) 0.2038(3) 0.2134(2) 0.0647(7) Uani 1 1 d . . . . .
H19 H 0.654402 0.120409 0.196792 0.078 Uiso 1 1 calc R U . . .
C20 C 0.5731(3) 0.2299(3) 0.1045(2) 0.0719(7) Uani 1 1 d . . . . .
H20 H 0.557619 0.164129 0.014811 0.086 Uiso 1 1 calc R U . . .
C21 C 0.5381(3) 0.3518(3) 0.1277(2) 0.0625(6) Uani 1 1 d . . . . .
H21 H 0.497949 0.368442 0.054298 0.075 Uiso 1 1 calc R U . . .
C22 C 0.5627(3) 0.4493(3) 0.2599(2) 0.0619(6) Uani 1 1 d . . . . .
H22 H 0.539416 0.532624 0.276042 0.074 Uiso 1 1 calc R U . . .
C23 C 0.6212(3) 0.4248(3) 0.3683(2) 0.0572(6) Uani 1 1 d . . . . .
H23 H 0.638443 0.492332 0.457563 0.069 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
Cl1 C15 1.739(2) . ?
N1 C1 1.412(2) . ?
N1 C5 1.387(2) . ?
N1 C6 1.403(2) . ?
N2 C1 1.324(2) . ?
N2 C11 1.374(2) . ?
C1 C2 1.423(3) . ?
C2 C3 1.364(3) . ?
C2 C12 1.481(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.414(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.347(3) . ?
C5 C18 1.480(3) . ?
C6 C7 1.389(3) . ?
C6 C11 1.401(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.396(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.362(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.399(3) . ?
C12 C13 1.381(3) . ?
C12 C17 1.387(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(4) . ?
C15 C16 1.366(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 C23 1.382(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.367(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.370(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.370(3) . ?
C23 H23 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
C5 N1 C1 122.54(17) . . ?
C5 N1 C6 131.45(17) . . ?
C6 N1 C1 105.97(14) . . ?
C1 N2 C11 105.06(15) . . ?
N1 C1 C2 118.85(16) . . ?
N2 C1 N1 112.28(16) . . ?
N2 C1 C2 128.86(17) . . ?
C1 C2 C12 120.41(17) . . ?
C3 C2 C1 117.43(19) . . ?
C3 C2 C12 122.16(19) . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.00(19) . . ?
C5 C4 H4 119.0 . . ?
N1 C5 C18 119.41(18) . . ?
C4 C5 N1 117.25(18) . . ?
C4 C5 C18 123.22(18) . . ?
C7 C6 N1 133.70(18) . . ?
C7 C6 C11 121.86(19) . . ?
C11 C6 N1 104.43(16) . . ?
C6 C7 H7 121.5 . . ?
C8 C7 C6 117.02(19) . . ?
C8 C7 H7 121.5 . . ?
C7 C8 H8 119.0 . . ?
C7 C8 C9 122.1(2) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.63(19) . . ?
C11 C10 H10 120.7 . . ?
N2 C11 C6 112.21(16) . . ?
N2 C11 C10 128.37(17) . . ?
C10 C11 C6 119.43(18) . . ?
C13 C12 C2 122.1(2) . . ?
C13 C12 C17 117.9(2) . . ?
C17 C12 C2 120.00(19) . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 Cl1 119.5(2) . . ?
C16 C15 Cl1 119.7(2) . . ?
C16 C15 C14 120.8(2) . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.2(2) . . ?
C17 C16 H16 120.4 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.5(2) . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C5 121.01(18) . . ?
C19 C18 C23 118.75(19) . . ?
C23 C18 C5 120.16(18) . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.6(2) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.6(2) . . ?
C22 C23 H23 119.7 . . ?

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
Cl1 C15 C16 C17 -178.23(17) . . . . ?
N1 C1 C2 C3 -0.1(3) . . . . ?
N1 C1 C2 C12 179.26(17) . . . . ?
N1 C5 C18 C19 -115.3(2) . . . . ?
N1 C5 C18 C23 68.0(3) . . . . ?
N1 C6 C7 C8 -178.60(19) . . . . ?
N1 C6 C11 N2 -1.9(2) . . . . ?
N1 C6 C11 C10 177.65(17) . . . . ?
N2 C1 C2 C3 -179.1(2) . . . . ?
N2 C1 C2 C12 0.2(3) . . . . ?
C1 N1 C5 C4 4.6(3) . . . . ?
C1 N1 C5 C18 -171.62(17) . . . . ?
C1 N1 C6 C7 -176.9(2) . . . . ?
C1 N1 C6 C11 2.17(18) . . . . ?
C1 N2 C11 C6 0.8(2) . . . . ?
C1 N2 C11 C10 -178.7(2) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C1 C2 C12 C13 44.2(3) . . . . ?
C1 C2 C12 C17 -136.9(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C12 C13 C14 179.1(2) . . . . ?
C2 C12 C17 C16 179.99(19) . . . . ?
C3 C2 C12 C13 -136.5(2) . . . . ?
C3 C2 C12 C17 42.4(3) . . . . ?
C3 C4 C5 N1 -3.2(3) . . . . ?
C3 C4 C5 C18 172.9(2) . . . . ?
C4 C5 C18 C19 68.7(3) . . . . ?
C4 C5 C18 C23 -108.0(3) . . . . ?
C5 N1 C1 N2 176.15(16) . . . . ?
C5 N1 C1 C2 -3.0(3) . . . . ?
C5 N1 C6 C7 5.4(3) . . . . ?
C5 N1 C6 C11 -175.57(19) . . . . ?
C5 C18 C19 C20 -177.5(2) . . . . ?
C5 C18 C23 C22 177.9(2) . . . . ?
C6 N1 C1 N2 -1.9(2) . . . . ?
C6 N1 C1 C2 178.96(16) . . . . ?
C6 N1 C5 C4 -177.96(19) . . . . ?
C6 N1 C5 C18 5.8(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C6 C11 N2 177.25(18) . . . . ?
C7 C6 C11 C10 -3.2(3) . . . . ?
C7 C8 C9 C10 -2.0(3) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C9 C10 C11 N2 -179.3(2) . . . . ?
C9 C10 C11 C6 1.2(3) . . . . ?
C11 N2 C1 N1 0.6(2) . . . . ?
C11 N2 C1 C2 179.74(19) . . . . ?
C11 C6 C7 C8 2.5(3) . . . . ?
C12 C2 C3 C4 -177.8(2) . . . . ?
C12 C13 C14 C15 1.6(4) . . . . ?
C13 C12 C17 C16 -1.1(3) . . . . ?
C13 C14 C15 Cl1 177.31(18) . . . . ?
C13 C14 C15 C16 -2.6(4) . . . . ?
C14 C15 C16 C17 1.7(4) . . . . ?
C15 C16 C17 C12 0.2(3) . . . . ?
C17 C12 C13 C14 0.2(3) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C19 C18 C23 C22 1.1(3) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C21 C22 C23 C18 -0.7(4) . . . . ?
C23 C18 C19 C20 -0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.808
_oxdiff_exptl_absorpt_empirical_full_min 0.765
####################################################################### 
# 
# 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_exp_8358
_database_code_depnum_ccdc_archive 'CCDC 2073473'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;School of Chemistry and Environment,South China Normal University
China
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_audit_creation_date             2021-01-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 N3 O2'
_chemical_formula_sum            'C23 H15 N3 O2'
_chemical_formula_weight         365.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           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                   9.9767(11)
_cell_length_b                   10.2000(11)
_cell_length_c                   10.3359(12)
_cell_angle_alpha                107.613(10)
_cell_angle_beta                 91.055(9)
_cell_angle_gamma                117.427(11)
_cell_volume                     874.20(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1322
_cell_measurement_temperature    297
_cell_measurement_theta_max      22.9760
_cell_measurement_theta_min      4.0900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6378
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.428
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  73.00   1.00    5.00    --   15.49  57.00 -60.00   46
  2  ω      0.00  58.00   1.00    5.00    --   15.49  57.00 -90.00   58
  3  ω    -13.00  85.00   1.00    5.00    --   15.49  19.00-150.00   98
  4  ω    -25.00   0.00   1.00    5.00    --  -16.28 -99.00  30.00   25
  5  ω    -25.00   0.00   1.00    5.00    --  -16.28 -99.00 120.00   25
  6  ω    -12.00  21.00   1.00    5.00    --  -16.28 -99.00 150.00   33
  7  ω    -30.00  47.00   1.00    5.00    --  -16.28  77.00  30.00   77
  8  ω     59.00  85.00   1.00    5.00    --   15.49 178.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0299963000
_diffrn_orient_matrix_UB_12      0.0232987000
_diffrn_orient_matrix_UB_13      -0.0462106000
_diffrn_orient_matrix_UB_21      0.0747763000
_diffrn_orient_matrix_UB_22      0.0425927000
_diffrn_orient_matrix_UB_23      -0.0128824000
_diffrn_orient_matrix_UB_31      -0.0124834000
_diffrn_orient_matrix_UB_32      -0.0681236000
_diffrn_orient_matrix_UB_33      -0.0554033000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1761
_reflns_number_total             3076
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      1.017
_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)+(0.0563P)²+0.0449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1541
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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 -0.0563(4) 0.8395(4) -0.2263(3) 0.1185(12) Uani 1 1 d . . . . .
O2 O -0.2281(4) 0.5987(4) -0.2675(3) 0.1145(11) Uani 1 1 d . . . . .
N1 N 0.3684(3) 0.7651(2) 0.44609(19) 0.0440(6) Uani 1 1 d . . . . .
N2 N 0.4087(3) 0.8093(3) 0.2440(2) 0.0481(6) Uani 1 1 d . . . . .
N3 N -0.1176(4) 0.7221(5) -0.1947(3) 0.0780(9) Uani 1 1 d . . . . .
C1 C 0.3076(4) 0.7715(3) 0.3252(3) 0.0453(8) Uani 1 1 d . . . . .
C2 C 0.1504(4) 0.7348(3) 0.3046(3) 0.0501(8) Uani 1 1 d . . . . .
C3 C 0.0692(4) 0.6986(4) 0.4040(3) 0.0647(9) Uani 1 1 d . . . . .
H3 H -0.032373 0.677231 0.393676 0.078 Uiso 1 1 calc R U . . .
C4 C 0.1345(4) 0.6923(4) 0.5229(3) 0.0672(10) Uani 1 1 d . . . . .
H4 H 0.074917 0.667813 0.589024 0.081 Uiso 1 1 calc R U . . .
C5 C 0.2807(4) 0.7208(3) 0.5432(3) 0.0503(8) Uani 1 1 d . . . . .
C6 C 0.5219(3) 0.8040(3) 0.4377(2) 0.0438(7) Uani 1 1 d . . . . .
C7 C 0.6428(4) 0.8219(3) 0.5238(3) 0.0538(8) Uani 1 1 d . . . . .
H7 H 0.630856 0.808680 0.608806 0.065 Uiso 1 1 calc R U . . .
C8 C 0.7783(4) 0.8593(4) 0.4800(3) 0.0608(9) Uani 1 1 d . . . . .
H8 H 0.859889 0.870249 0.535566 0.073 Uiso 1 1 calc R U . . .
C9 C 0.7990(4) 0.8820(3) 0.3533(3) 0.0625(9) Uani 1 1 d . . . . .
H9 H 0.893883 0.907846 0.326611 0.075 Uiso 1 1 calc R U . . .
C10 C 0.6821(4) 0.8667(3) 0.2682(3) 0.0560(8) Uani 1 1 d . . . . .
H10 H 0.695960 0.880455 0.183540 0.067 Uiso 1 1 calc R U . . .
C11 C 0.5411(3) 0.8297(3) 0.3116(3) 0.0443(7) Uani 1 1 d . . . . .
C12 C 0.0814(4) 0.7358(4) 0.1771(3) 0.0480(8) Uani 1 1 d . . . . .
C13 C 0.1589(4) 0.8542(4) 0.1235(3) 0.0618(9) Uani 1 1 d . . . . .
H13 H 0.257221 0.935278 0.168214 0.074 Uiso 1 1 calc R U . . .
C14 C 0.0922(4) 0.8536(4) 0.0046(3) 0.0651(9) Uani 1 1 d . . . . .
H14 H 0.142747 0.935755 -0.028569 0.078 Uiso 1 1 calc R U . . .
C15 C -0.0503(4) 0.7288(4) -0.0636(3) 0.0588(9) Uani 1 1 d . . . . .
C16 C -0.1315(4) 0.6091(4) -0.0140(3) 0.0652(9) Uani 1 1 d . . . . .
H16 H -0.228750 0.527006 -0.060722 0.078 Uiso 1 1 calc R U . . .
C17 C -0.0650(4) 0.6138(4) 0.1069(3) 0.0615(9) Uani 1 1 d . . . . .
H17 H -0.118703 0.534235 0.142199 0.074 Uiso 1 1 calc R U . . .
C18 C 0.3474(4) 0.7001(3) 0.6597(3) 0.0512(8) Uani 1 1 d . . . . .
C19 C 0.3749(4) 0.5734(4) 0.6366(3) 0.0584(9) Uani 1 1 d . . . . .
H19 H 0.354904 0.503897 0.547045 0.070 Uiso 1 1 calc R U . . .
C20 C 0.4310(4) 0.5510(4) 0.7446(3) 0.0627(9) Uani 1 1 d . . . . .
H20 H 0.449391 0.466429 0.728011 0.075 Uiso 1 1 calc R U . . .
C21 C 0.4605(4) 0.6521(4) 0.8779(3) 0.0649(9) Uani 1 1 d . . . . .
H21 H 0.499603 0.636679 0.950900 0.078 Uiso 1 1 calc R U . . .
C22 C 0.4320(4) 0.7754(4) 0.9021(3) 0.0730(11) Uani 1 1 d . . . . .
H22 H 0.450701 0.843322 0.992135 0.088 Uiso 1 1 calc R U . . .
C23 C 0.3754(4) 0.7997(4) 0.7936(3) 0.0675(10) Uani 1 1 d . . . . .
H23 H 0.356123 0.883780 0.811107 0.081 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 N3 1.218(4) . ?
O2 N3 1.218(4) . ?
N1 C1 1.410(3) . ?
N1 C5 1.385(3) . ?
N1 C6 1.406(3) . ?
N2 C1 1.319(3) . ?
N2 C11 1.379(3) . ?
N3 C15 1.469(4) . ?
C1 C2 1.429(4) . ?
C2 C3 1.354(4) . ?
C2 C12 1.480(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.412(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.348(4) . ?
C5 C18 1.481(4) . ?
C6 C7 1.393(4) . ?
C6 C11 1.406(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.352(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.400(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.400(4) . ?
C12 C13 1.387(4) . ?
C12 C17 1.395(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(4) . ?
C15 C16 1.376(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.394(4) . ?
C18 C23 1.378(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.365(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.366(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(4) . ?
C23 H23 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
C5 N1 C1 122.6(2) . . ?
C5 N1 C6 131.4(2) . . ?
C6 N1 C1 105.9(2) . . ?
C1 N2 C11 105.1(2) . . ?
O1 N3 O2 123.6(3) . . ?
O1 N3 C15 117.8(3) . . ?
O2 N3 C15 118.5(4) . . ?
N1 C1 C2 118.5(3) . . ?
N2 C1 N1 112.6(3) . . ?
N2 C1 C2 128.9(2) . . ?
C1 C2 C12 120.0(3) . . ?
C3 C2 C1 117.7(3) . . ?
C3 C2 C12 122.3(3) . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.9(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.1 . . ?
N1 C5 C18 119.6(3) . . ?
C4 C5 N1 117.4(2) . . ?
C4 C5 C18 123.0(3) . . ?
N1 C6 C11 104.4(2) . . ?
C7 C6 N1 134.4(3) . . ?
C7 C6 C11 121.2(3) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 C6 117.9(3) . . ?
C8 C7 H7 121.0 . . ?
C7 C8 H8 119.1 . . ?
C7 C8 C9 121.8(3) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.3(3) . . ?
C11 C10 H10 120.8 . . ?
N2 C11 C6 111.9(3) . . ?
N2 C11 C10 128.5(3) . . ?
C10 C11 C6 119.6(3) . . ?
C13 C12 C2 121.9(3) . . ?
C13 C12 C17 118.5(3) . . ?
C17 C12 C2 119.7(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.6(3) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 N3 118.9(3) . . ?
C14 C15 C16 122.3(3) . . ?
C16 C15 N3 118.8(3) . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.3(3) . . ?
C17 C16 H16 120.8 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.2(3) . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C5 120.3(2) . . ?
C23 C18 C5 120.9(3) . . ?
C23 C18 C19 118.6(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.7(3) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.4(3) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?

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 N3 C15 C14 -11.8(5) . . . . ?
O1 N3 C15 C16 168.9(3) . . . . ?
O2 N3 C15 C14 166.0(3) . . . . ?
O2 N3 C15 C16 -13.3(5) . . . . ?
N1 C1 C2 C3 1.1(4) . . . . ?
N1 C1 C2 C12 -178.3(2) . . . . ?
N1 C5 C18 C19 -70.3(4) . . . . ?
N1 C5 C18 C23 113.5(3) . . . . ?
N1 C6 C7 C8 179.2(3) . . . . ?
N1 C6 C11 N2 0.3(3) . . . . ?
N1 C6 C11 C10 -178.1(2) . . . . ?
N2 C1 C2 C3 179.7(3) . . . . ?
N2 C1 C2 C12 0.3(5) . . . . ?
N3 C15 C16 C17 177.8(3) . . . . ?
C1 N1 C5 C4 -4.0(4) . . . . ?
C1 N1 C5 C18 173.4(2) . . . . ?
C1 N1 C6 C7 178.2(3) . . . . ?
C1 N1 C6 C11 -0.4(3) . . . . ?
C1 N2 C11 C6 0.0(3) . . . . ?
C1 N2 C11 C10 178.1(3) . . . . ?
C1 C2 C3 C4 -1.8(5) . . . . ?
C1 C2 C12 C13 -43.3(4) . . . . ?
C1 C2 C12 C17 135.8(3) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C2 C12 C13 C14 -179.7(3) . . . . ?
C2 C12 C17 C16 -178.5(3) . . . . ?
C3 C2 C12 C13 137.3(3) . . . . ?
C3 C2 C12 C17 -43.6(4) . . . . ?
C3 C4 C5 N1 3.4(5) . . . . ?
C3 C4 C5 C18 -173.9(3) . . . . ?
C4 C5 C18 C19 107.0(4) . . . . ?
C4 C5 C18 C23 -69.3(4) . . . . ?
C5 N1 C1 N2 -177.0(2) . . . . ?
C5 N1 C1 C2 1.8(4) . . . . ?
C5 N1 C6 C7 -4.7(5) . . . . ?
C5 N1 C6 C11 176.7(3) . . . . ?
C5 C18 C19 C20 -177.5(3) . . . . ?
C5 C18 C23 C22 177.4(3) . . . . ?
C6 N1 C1 N2 0.4(3) . . . . ?
C6 N1 C1 C2 179.2(2) . . . . ?
C6 N1 C5 C4 179.3(3) . . . . ?
C6 N1 C5 C18 -3.3(4) . . . . ?
C6 C7 C8 C9 0.9(4) . . . . ?
C7 C6 C11 N2 -178.5(2) . . . . ?
C7 C6 C11 C10 3.1(4) . . . . ?
C7 C8 C9 C10 -0.2(5) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C10 C11 N2 179.7(3) . . . . ?
C9 C10 C11 C6 -2.3(4) . . . . ?
C11 N2 C1 N1 -0.2(3) . . . . ?
C11 N2 C1 C2 -178.9(3) . . . . ?
C11 C6 C7 C8 -2.4(4) . . . . ?
C12 C2 C3 C4 177.6(3) . . . . ?
C12 C13 C14 C15 -3.0(5) . . . . ?
C13 C12 C17 C16 0.6(5) . . . . ?
C13 C14 C15 N3 -176.1(3) . . . . ?
C13 C14 C15 C16 3.2(5) . . . . ?
C14 C15 C16 C17 -1.4(5) . . . . ?
C15 C16 C17 C12 -0.5(5) . . . . ?
C17 C12 C13 C14 1.1(4) . . . . ?
C18 C19 C20 C21 0.3(5) . . . . ?
C19 C18 C23 C22 1.1(5) . . . . ?
C19 C20 C21 C22 0.6(5) . . . . ?
C20 C21 C22 C23 -0.7(6) . . . . ?
C21 C22 C23 C18 -0.1(5) . . . . ?
C23 C18 C19 C20 -1.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.872
####################################################################### 
# 
# 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_exp_9112
_database_code_depnum_ccdc_archive 'CCDC 2073465'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;School of Chemistry and Environment,South China Normal University
China
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 Cl N2'
_chemical_formula_sum            'C25 H19 Cl N2'
_chemical_formula_weight         382.87
_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'
Cl Cl 0.1484 0.1585 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.0520(9)
_cell_length_b                   10.4783(11)
_cell_length_c                   18.7614(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.129(8)
_cell_angle_gamma                90
_cell_volume                     1973.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2245
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5280
_cell_measurement_theta_min      4.0340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8419
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.486
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  77.00   1.00    5.00    --   15.65   0.00 -90.00  129
  2  ω    -11.00  18.00   1.00    5.00    --  -16.43 -99.00 -90.00   29
  3  ω    -25.00  21.00   1.00    5.00    --  -16.43 -99.00  90.00   46
  4  ω    -25.00  10.00   1.00    5.00    --   15.65 -99.00 120.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0105796000
_diffrn_orient_matrix_UB_12      0.0593225000
_diffrn_orient_matrix_UB_13      -0.0176214000
_diffrn_orient_matrix_UB_21      0.0565065000
_diffrn_orient_matrix_UB_22      0.0256905000
_diffrn_orient_matrix_UB_23      0.0192395000
_diffrn_orient_matrix_UB_31      0.0410952000
_diffrn_orient_matrix_UB_32      -0.0200682000
_diffrn_orient_matrix_UB_33      -0.0274426000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2297
_reflns_number_total             3462
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.036
_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     255
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+0.2327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1327
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C21(H21A,H21B,H21C)
;
_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
Cl1 Cl 0.58302(9) 0.24542(9) 0.10061(4) 0.0808(3) Uani 1 1 d . . . . .
N1 N 0.65505(19) 0.60668(19) 0.49160(9) 0.0378(5) Uani 1 1 d . . . . .
N2 N 0.5137(2) 0.6233(2) 0.39357(10) 0.0436(5) Uani 1 1 d . . . . .
C1 C 0.6190(2) 0.5632(2) 0.42233(11) 0.0383(6) Uani 1 1 d . . . . .
C2 C 0.3463(3) 0.8652(3) 0.50227(15) 0.0529(7) Uani 1 1 d . . . . .
C3 C 0.8436(3) 0.6061(5) 0.72808(16) 0.0852(12) Uani 1 1 d . . . . .
H3 H 0.840297 0.559878 0.770268 0.102 Uiso 1 1 calc R U . . .
C4 C 0.5613(2) 0.7010(2) 0.50664(12) 0.0382(6) Uani 1 1 d . . . . .
C5 C 0.8902(3) 0.7285(5) 0.7301(2) 0.0891(13) Uani 1 1 d . . . . .
H5 H 0.916695 0.766150 0.773438 0.107 Uiso 1 1 calc R U . . .
C6 C 0.4772(2) 0.7080(2) 0.44545(12) 0.0412(6) Uani 1 1 d . . . . .
C7 C 0.7667(3) 0.3629(3) 0.28107(14) 0.0556(8) Uani 1 1 d . . . . .
H7 H 0.853751 0.364569 0.300633 0.067 Uiso 1 1 calc R U . . .
C8 C 0.6656(2) 0.4144(2) 0.31984(12) 0.0422(6) Uani 1 1 d . . . . .
C9 C 0.8011(3) 0.5498(3) 0.66389(14) 0.0630(9) Uani 1 1 d . . . . .
H9 H 0.770082 0.466212 0.663147 0.076 Uiso 1 1 calc R U . . .
C10 C 0.6955(2) 0.4632(2) 0.39292(12) 0.0401(6) Uani 1 1 d . . . . .
C11 C 0.2281(3) 0.9544(3) 0.50032(18) 0.0823(11) Uani 1 1 d . . . . .
H11A H 0.183311 0.951709 0.453823 0.124 Uiso 1 1 calc R U . . .
H11B H 0.258120 1.039750 0.510439 0.124 Uiso 1 1 calc R U . . .
H11C H 0.167706 0.928271 0.535470 0.124 Uiso 1 1 calc R U . . .
C12 C 0.7631(2) 0.5589(2) 0.53218(12) 0.0416(6) Uani 1 1 d . . . . .
C13 C 0.4317(3) 0.8559(3) 0.56432(14) 0.0514(7) Uani 1 1 d . . . . .
C14 C 0.8050(2) 0.6178(3) 0.60142(13) 0.0473(7) Uani 1 1 d . . . . .
C15 C 0.5124(3) 0.3597(3) 0.22165(14) 0.0583(8) Uani 1 1 d . . . . .
H15 H 0.425878 0.358377 0.201410 0.070 Uiso 1 1 calc R U . . .
C16 C 0.8298(3) 0.4607(3) 0.50430(13) 0.0497(7) Uani 1 1 d . . . . .
H16 H 0.899863 0.423436 0.531223 0.060 Uiso 1 1 calc R U . . .
C17 C 0.7420(3) 0.3097(3) 0.21467(14) 0.0594(8) Uani 1 1 d . . . . .
H17 H 0.811089 0.274597 0.190137 0.071 Uiso 1 1 calc R U . . .
C18 C 0.7962(3) 0.4135(3) 0.43578(13) 0.0488(7) Uani 1 1 d . . . . .
H18 H 0.844705 0.345409 0.418880 0.059 Uiso 1 1 calc R U . . .
C19 C 0.8554(3) 0.7407(3) 0.60368(16) 0.0635(8) Uani 1 1 d . . . . .
H19 H 0.860846 0.786943 0.561620 0.076 Uiso 1 1 calc R U . . .
C20 C 0.3694(3) 0.7919(3) 0.44326(14) 0.0506(7) Uani 1 1 d . . . . .
H20 H 0.313496 0.798251 0.402257 0.061 Uiso 1 1 calc R U . . .
C21 C 0.4051(3) 0.9341(3) 0.62987(16) 0.0766(10) Uani 1 1 d . . . . .
H21A H 0.468455 0.911639 0.667965 0.115 Uiso 1 1 calc R U . . .
H21B H 0.316625 0.917049 0.644157 0.115 Uiso 1 1 calc R U . . .
H21C H 0.413532 1.023191 0.619061 0.115 Uiso 1 1 calc R U . . .
C22 C 0.5385(3) 0.7736(2) 0.56658(13) 0.0475(7) Uani 1 1 d . . . . .
H22 H 0.594379 0.766750 0.607565 0.057 Uiso 1 1 calc R U . . .
C23 C 0.8976(3) 0.7952(4) 0.66800(19) 0.0827(11) Uani 1 1 d . . . . .
H23 H 0.931270 0.877892 0.669002 0.099 Uiso 1 1 calc R U . . .
C24 C 0.5381(3) 0.4122(3) 0.28793(13) 0.0532(7) Uani 1 1 d . . . . .
H24 H 0.468338 0.447160 0.312000 0.064 Uiso 1 1 calc R U . . .
C25 C 0.6151(3) 0.3089(3) 0.18523(13) 0.0518(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C25 1.735(3) . ?
N1 C1 1.406(3) . ?
N1 C4 1.405(3) . ?
N1 C12 1.386(3) . ?
N2 C1 1.321(3) . ?
N2 C6 1.382(3) . ?
C1 C10 1.428(3) . ?
C2 C11 1.511(4) . ?
C2 C13 1.411(4) . ?
C2 C20 1.378(4) . ?
C3 H3 0.9300 . ?
C3 C5 1.366(5) . ?
C3 C9 1.387(4) . ?
C4 C6 1.390(3) . ?
C4 C22 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C23 1.363(5) . ?
C6 C20 1.394(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(3) . ?
C7 C17 1.375(3) . ?
C8 C10 1.479(3) . ?
C8 C24 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C14 1.374(3) . ?
C10 C18 1.361(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C14 1.478(3) . ?
C12 C16 1.349(3) . ?
C13 C21 1.513(3) . ?
C13 C22 1.376(4) . ?
C14 C19 1.384(4) . ?
C15 H15 0.9300 . ?
C15 C24 1.372(3) . ?
C15 C25 1.376(4) . ?
C16 H16 0.9300 . ?
C16 C18 1.401(3) . ?
C17 H17 0.9300 . ?
C17 C25 1.362(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C23 1.381(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
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 C1 105.77(18) . . ?
C12 N1 C1 123.1(2) . . ?
C12 N1 C4 131.2(2) . . ?
C1 N2 C6 104.85(19) . . ?
N1 C1 C10 118.6(2) . . ?
N2 C1 N1 112.5(2) . . ?
N2 C1 C10 128.9(2) . . ?
C13 C2 C11 120.3(3) . . ?
C20 C2 C11 119.5(3) . . ?
C20 C2 C13 120.2(3) . . ?
C5 C3 H3 119.6 . . ?
C5 C3 C9 120.8(3) . . ?
C9 C3 H3 119.6 . . ?
C6 C4 N1 104.8(2) . . ?
C22 C4 N1 133.7(2) . . ?
C22 C4 C6 121.4(2) . . ?
C3 C5 H5 120.2 . . ?
C23 C5 C3 119.5(3) . . ?
C23 C5 H5 120.2 . . ?
N2 C6 C4 112.0(2) . . ?
N2 C6 C20 128.3(2) . . ?
C4 C6 C20 119.6(2) . . ?
C8 C7 H7 119.0 . . ?
C17 C7 H7 119.0 . . ?
C17 C7 C8 122.0(3) . . ?
C7 C8 C10 120.1(2) . . ?
C24 C8 C7 116.9(2) . . ?
C24 C8 C10 122.9(2) . . ?
C3 C9 H9 120.0 . . ?
C14 C9 C3 119.9(3) . . ?
C14 C9 H9 120.0 . . ?
C1 C10 C8 121.7(2) . . ?
C18 C10 C1 116.8(2) . . ?
C18 C10 C8 121.5(2) . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C14 120.6(2) . . ?
C16 C12 N1 117.0(2) . . ?
C16 C12 C14 122.4(2) . . ?
C2 C13 C21 120.5(3) . . ?
C22 C13 C2 120.4(2) . . ?
C22 C13 C21 119.1(3) . . ?
C9 C14 C12 120.9(3) . . ?
C9 C14 C19 118.9(3) . . ?
C19 C14 C12 120.1(2) . . ?
C24 C15 H15 120.1 . . ?
C24 C15 C25 119.7(3) . . ?
C25 C15 H15 120.1 . . ?
C12 C16 H16 119.2 . . ?
C12 C16 C18 121.7(2) . . ?
C18 C16 H16 119.2 . . ?
C7 C17 H17 120.4 . . ?
C25 C17 C7 119.3(2) . . ?
C25 C17 H17 120.4 . . ?
C10 C18 C16 122.8(2) . . ?
C10 C18 H18 118.6 . . ?
C16 C18 H18 118.6 . . ?
C14 C19 H19 119.8 . . ?
C23 C19 C14 120.4(3) . . ?
C23 C19 H19 119.8 . . ?
C2 C20 C6 119.5(2) . . ?
C2 C20 H20 120.2 . . ?
C6 C20 H20 120.2 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C22 H22 120.6 . . ?
C13 C22 C4 118.8(2) . . ?
C13 C22 H22 120.6 . . ?
C5 C23 C19 120.4(4) . . ?
C5 C23 H23 119.8 . . ?
C19 C23 H23 119.8 . . ?
C8 C24 H24 119.2 . . ?
C15 C24 C8 121.5(2) . . ?
C15 C24 H24 119.2 . . ?
C15 C25 Cl1 119.7(2) . . ?
C17 C25 Cl1 119.8(2) . . ?
C17 C25 C15 120.5(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
N1 C1 C10 C8 -178.6(2) . . . . ?
N1 C1 C10 C18 2.3(3) . . . . ?
N1 C4 C6 N2 0.1(3) . . . . ?
N1 C4 C6 C20 178.5(2) . . . . ?
N1 C4 C22 C13 -177.2(3) . . . . ?
N1 C12 C14 C9 117.1(3) . . . . ?
N1 C12 C14 C19 -66.2(3) . . . . ?
N1 C12 C16 C18 3.4(4) . . . . ?
N2 C1 C10 C8 2.2(4) . . . . ?
N2 C1 C10 C18 -176.8(2) . . . . ?
N2 C6 C20 C2 177.0(2) . . . . ?
C1 N1 C4 C6 -0.6(2) . . . . ?
C1 N1 C4 C22 175.8(3) . . . . ?
C1 N1 C12 C14 173.3(2) . . . . ?
C1 N1 C12 C16 -4.3(4) . . . . ?
C1 N2 C6 C4 0.5(3) . . . . ?
C1 N2 C6 C20 -177.8(3) . . . . ?
C1 C10 C18 C16 -3.2(4) . . . . ?
C2 C13 C22 C4 0.6(4) . . . . ?
C3 C5 C23 C19 1.5(5) . . . . ?
C3 C9 C14 C12 178.6(2) . . . . ?
C3 C9 C14 C19 1.9(4) . . . . ?
C4 N1 C1 N2 0.9(3) . . . . ?
C4 N1 C1 C10 -178.4(2) . . . . ?
C4 N1 C12 C14 -7.0(4) . . . . ?
C4 N1 C12 C16 175.4(2) . . . . ?
C4 C6 C20 C2 -1.1(4) . . . . ?
C5 C3 C9 C14 -0.4(5) . . . . ?
C6 N2 C1 N1 -0.9(3) . . . . ?
C6 N2 C1 C10 178.4(2) . . . . ?
C6 C4 C22 C13 -1.3(4) . . . . ?
C7 C8 C10 C1 151.6(2) . . . . ?
C7 C8 C10 C18 -29.4(4) . . . . ?
C7 C8 C24 C15 1.1(4) . . . . ?
C7 C17 C25 Cl1 178.5(2) . . . . ?
C7 C17 C25 C15 -0.6(5) . . . . ?
C8 C7 C17 C25 1.1(4) . . . . ?
C8 C10 C18 C16 177.7(2) . . . . ?
C9 C3 C5 C23 -1.4(5) . . . . ?
C9 C14 C19 C23 -1.7(4) . . . . ?
C10 C8 C24 C15 -176.2(3) . . . . ?
C11 C2 C13 C21 0.6(4) . . . . ?
C11 C2 C13 C22 179.2(3) . . . . ?
C11 C2 C20 C6 -179.0(3) . . . . ?
C12 N1 C1 N2 -179.3(2) . . . . ?
C12 N1 C1 C10 1.4(3) . . . . ?
C12 N1 C4 C6 179.7(2) . . . . ?
C12 N1 C4 C22 -4.0(4) . . . . ?
C12 C14 C19 C23 -178.5(3) . . . . ?
C12 C16 C18 C10 0.3(4) . . . . ?
C13 C2 C20 C6 0.4(4) . . . . ?
C14 C12 C16 C18 -174.1(2) . . . . ?
C14 C19 C23 C5 0.0(5) . . . . ?
C16 C12 C14 C9 -65.5(3) . . . . ?
C16 C12 C14 C19 111.2(3) . . . . ?
C17 C7 C8 C10 176.1(3) . . . . ?
C17 C7 C8 C24 -1.3(4) . . . . ?
C20 C2 C13 C21 -178.7(3) . . . . ?
C20 C2 C13 C22 -0.1(4) . . . . ?
C21 C13 C22 C4 179.2(2) . . . . ?
C22 C4 C6 N2 -176.8(2) . . . . ?
C22 C4 C6 C20 1.6(4) . . . . ?
C24 C8 C10 C1 -31.2(4) . . . . ?
C24 C8 C10 C18 147.8(3) . . . . ?
C24 C15 C25 Cl1 -178.7(2) . . . . ?
C24 C15 C25 C17 0.4(5) . . . . ?
C25 C15 C24 C8 -0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.723
_oxdiff_exptl_absorpt_empirical_full_min 0.545
####################################################################### 
# 
# 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_exp_8356
_database_code_depnum_ccdc_archive 'CCDC 2073808'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;School of Chemistry and Environment,South China Normal University
China
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_audit_creation_date             2021-01-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 N2'
_chemical_formula_sum            'C24 H18 N2'
_chemical_formula_weight         334.40
_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'

_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                   9.9393(11)
_cell_length_b                   10.0786(16)
_cell_length_c                   10.2828(11)
_cell_angle_alpha                106.688(12)
_cell_angle_beta                 91.551(9)
_cell_angle_gamma                116.591(13)
_cell_volume                     867.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1490
_cell_measurement_temperature    297
_cell_measurement_theta_max      25.0950
_cell_measurement_theta_min      3.9550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6873
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.397
_diffrn_reflns_theta_min         3.682
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  82.00   1.00    2.00    --   15.65  37.00  60.00   86
  2  ω    -17.00  31.00   1.00    2.00    --   15.65 -57.00 -90.00   48
  3  ω    -12.00  23.00   1.00    2.00    --  -16.28 -99.00  30.00   35
  4  ω    -25.00  12.00   1.00    2.00    --   15.65 -99.00 150.00   37
  5  ω    -49.00  21.00   1.00    2.00    --   15.65 -57.00-120.00   70
  6  ω    -69.00 -23.00   1.00    2.00    --  -16.28 127.00 121.00   46
  7  ω     37.00  72.00   1.00    2.00    --   15.65 178.00-120.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0522723000
_diffrn_orient_matrix_UB_12      -0.0284202000
_diffrn_orient_matrix_UB_13      0.0079737000
_diffrn_orient_matrix_UB_21      0.0058194000
_diffrn_orient_matrix_UB_22      0.0273590000
_diffrn_orient_matrix_UB_23      0.0726920000
_diffrn_orient_matrix_UB_31      -0.0618043000
_diffrn_orient_matrix_UB_32      -0.0736180000
_diffrn_orient_matrix_UB_33      -0.0038786000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2334
_reflns_number_total             3953
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.050
_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)+(0.0537P)²+0.0654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1464
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 0.59072(15) 0.19275(18) 0.76743(14) 0.0467(4) Uani 1 1 d . . . . .
N2 N 0.62992(16) 0.23368(17) 0.56301(14) 0.0434(4) Uani 1 1 d . . . . .
C1 C 0.69121(19) 0.2291(2) 0.68502(17) 0.0425(4) Uani 1 1 d . . . . .
C2 C 0.8482(2) 0.2645(2) 0.70744(19) 0.0495(5) Uani 1 1 d . . . . .
C3 C 0.9286(2) 0.3014(3) 0.6073(2) 0.0630(6) Uani 1 1 d . . . . .
H3 H 1.030287 0.322899 0.617942 0.076 Uiso 1 1 calc R U . . .
C4 C 0.8634(2) 0.3084(3) 0.4875(2) 0.0665(6) Uani 1 1 d . . . . .
H4 H 0.923714 0.334882 0.422130 0.080 Uiso 1 1 calc R U . . .
C5 C 0.7166(2) 0.2779(2) 0.46456(18) 0.0507(5) Uani 1 1 d . . . . .
C6 C 0.47611(19) 0.1923(2) 0.56943(17) 0.0437(4) Uani 1 1 d . . . . .
C7 C 0.3548(2) 0.1710(2) 0.48005(19) 0.0543(5) Uani 1 1 d . . . . .
H7 H 0.365889 0.180531 0.393154 0.065 Uiso 1 1 calc R U . . .
C8 C 0.2184(2) 0.1355(2) 0.5252(2) 0.0627(6) Uani 1 1 d . . . . .
H8 H 0.135624 0.121499 0.467944 0.075 Uiso 1 1 calc R U . . .
C9 C 0.2007(2) 0.1200(2) 0.6545(2) 0.0615(6) Uani 1 1 d . . . . .
H9 H 0.107004 0.097904 0.682535 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3175(2) 0.1364(2) 0.7412(2) 0.0542(5) Uani 1 1 d . . . . .
H10 H 0.304117 0.124508 0.827108 0.065 Uiso 1 1 calc R U . . .
C11 C 0.45802(19) 0.1717(2) 0.69781(18) 0.0443(4) Uani 1 1 d . . . . .
C12 C 0.9178(2) 0.2625(2) 0.83491(19) 0.0495(5) Uani 1 1 d . . . . .
C13 C 0.8436(2) 0.1447(3) 0.8910(2) 0.0629(6) Uani 1 1 d . . . . .
H13 H 0.745229 0.064602 0.848740 0.076 Uiso 1 1 calc R U . . .
C14 C 0.9134(2) 0.1444(3) 1.0087(2) 0.0738(7) Uani 1 1 d . . . . .
H14 H 0.861218 0.063126 1.043321 0.089 Uiso 1 1 calc R U . . .
C15 C 1.0579(3) 0.2610(3) 1.0762(2) 0.0677(6) Uani 1 1 d . . . . .
C16 C 1.1319(2) 0.3779(3) 1.0198(2) 0.0701(6) Uani 1 1 d . . . . .
H16 H 1.229989 0.458040 1.062829 0.084 Uiso 1 1 calc R U . . .
C17 C 1.0647(2) 0.3794(3) 0.9019(2) 0.0633(6) Uani 1 1 d . . . . .
H17 H 1.118268 0.459637 0.866481 0.076 Uiso 1 1 calc R U . . .
C18 C 1.1304(3) 0.2627(4) 1.2077(3) 0.1022(10) Uani 1 1 d . . . . .
H18A H 1.210124 0.234627 1.189395 0.153 Uiso 1 1 calc R U . . .
H18B H 1.054355 0.188377 1.242446 0.153 Uiso 1 1 calc R U . . .
H18C H 1.172987 0.366261 1.275105 0.153 Uiso 1 1 calc R U . . .
C19 C 0.6502(2) 0.2999(2) 0.34696(18) 0.0498(5) Uani 1 1 d . . . . .
C20 C 0.6261(3) 0.2030(3) 0.2140(2) 0.0660(6) Uani 1 1 d . . . . .
H20 H 0.646020 0.118425 0.197934 0.079 Uiso 1 1 calc R U . . .
C21 C 0.5730(3) 0.2297(3) 0.1045(2) 0.0725(7) Uani 1 1 d . . . . .
H21 H 0.558071 0.163896 0.014931 0.087 Uiso 1 1 calc R U . . .
C22 C 0.5419(2) 0.3529(3) 0.1270(2) 0.0636(6) Uani 1 1 d . . . . .
H22 H 0.504584 0.369929 0.052849 0.076 Uiso 1 1 calc R U . . .
C23 C 0.5659(2) 0.4512(3) 0.2591(2) 0.0632(6) Uani 1 1 d . . . . .
H23 H 0.545281 0.535219 0.274573 0.076 Uiso 1 1 calc R U . . .
C24 C 0.6205(2) 0.4256(2) 0.3684(2) 0.0605(6) Uani 1 1 d . . . . .
H24 H 0.637632 0.493194 0.457725 0.073 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 C1 1.321(2) . ?
N1 C11 1.381(2) . ?
N2 C1 1.402(2) . ?
N2 C5 1.389(2) . ?
N2 C6 1.402(2) . ?
C1 C2 1.432(3) . ?
C2 C3 1.355(2) . ?
C2 C12 1.475(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.411(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.348(3) . ?
C5 C19 1.479(2) . ?
C6 C7 1.393(2) . ?
C6 C11 1.398(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.399(2) . ?
C12 C13 1.385(3) . ?
C12 C17 1.391(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(3) . ?
C15 C16 1.380(3) . ?
C15 C18 1.508(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.373(3) . ?
C19 C24 1.385(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.368(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.372(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.372(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
C1 N1 C11 104.75(14) . . ?
C1 N2 C6 106.11(13) . . ?
C5 N2 C1 122.87(14) . . ?
C5 N2 C6 130.98(15) . . ?
N1 C1 N2 112.67(14) . . ?
N1 C1 C2 128.22(16) . . ?
N2 C1 C2 119.11(15) . . ?
C1 C2 C12 120.94(15) . . ?
C3 C2 C1 116.78(17) . . ?
C3 C2 C12 122.28(17) . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.27(18) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.27(18) . . ?
C5 C4 H4 118.9 . . ?
N2 C5 C19 120.10(16) . . ?
C4 C5 N2 116.62(17) . . ?
C4 C5 C19 123.15(17) . . ?
C7 C6 N2 134.09(16) . . ?
C7 C6 C11 121.45(17) . . ?
C11 C6 N2 104.46(15) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.37(18) . . ?
C8 C7 H7 121.3 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.59(19) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.48(19) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.34(18) . . ?
C11 C10 H10 120.8 . . ?
N1 C11 C6 111.96(15) . . ?
N1 C11 C10 128.34(16) . . ?
C6 C11 C10 119.69(17) . . ?
C13 C12 C2 122.43(17) . . ?
C13 C12 C17 117.29(19) . . ?
C17 C12 C2 120.26(18) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.95(19) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 121.9(2) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C16 117.1(2) . . ?
C14 C15 C18 121.4(2) . . ?
C16 C15 C18 121.6(2) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.9(2) . . ?
C17 C16 H16 119.1 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 120.9(2) . . ?
C16 C17 H17 119.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C5 121.00(18) . . ?
C20 C19 C24 118.63(18) . . ?
C24 C19 C5 120.24(17) . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.7(2) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.8(2) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.59(19) . . ?
C23 C24 H24 119.7 . . ?

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 C1 C2 C3 -178.72(18) . . . . ?
N1 C1 C2 C12 0.4(3) . . . . ?
N2 C1 C2 C3 0.3(3) . . . . ?
N2 C1 C2 C12 179.43(15) . . . . ?
N2 C5 C19 C20 -114.7(2) . . . . ?
N2 C5 C19 C24 69.6(2) . . . . ?
N2 C6 C7 C8 -177.50(19) . . . . ?
N2 C6 C11 N1 -2.1(2) . . . . ?
N2 C6 C11 C10 176.95(17) . . . . ?
C1 N1 C11 C6 1.2(2) . . . . ?
C1 N1 C11 C10 -177.82(19) . . . . ?
C1 N2 C5 C4 3.7(3) . . . . ?
C1 N2 C5 C19 -172.21(16) . . . . ?
C1 N2 C6 C7 -177.65(19) . . . . ?
C1 N2 C6 C11 2.16(18) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C1 C2 C12 C13 43.5(3) . . . . ?
C1 C2 C12 C17 -138.1(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C2 C12 C13 C14 178.51(19) . . . . ?
C2 C12 C17 C16 -179.15(19) . . . . ?
C3 C2 C12 C13 -137.4(2) . . . . ?
C3 C2 C12 C17 41.0(3) . . . . ?
C3 C4 C5 N2 -2.1(3) . . . . ?
C3 C4 C5 C19 173.69(19) . . . . ?
C4 C5 C19 C20 69.6(3) . . . . ?
C4 C5 C19 C24 -106.1(2) . . . . ?
C5 N2 C1 N1 176.27(16) . . . . ?
C5 N2 C1 C2 -2.9(3) . . . . ?
C5 N2 C6 C7 4.7(3) . . . . ?
C5 N2 C6 C11 -175.50(17) . . . . ?
C5 C19 C20 C21 -176.10(19) . . . . ?
C5 C19 C24 C23 176.79(17) . . . . ?
C6 N2 C1 N1 -1.63(19) . . . . ?
C6 N2 C1 C2 179.23(16) . . . . ?
C6 N2 C5 C4 -178.94(19) . . . . ?
C6 N2 C5 C19 5.1(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C6 C11 N1 177.73(16) . . . . ?
C7 C6 C11 C10 -3.2(3) . . . . ?
C7 C8 C9 C10 -1.3(3) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 N1 -179.72(18) . . . . ?
C9 C10 C11 C6 1.4(3) . . . . ?
C11 N1 C1 N2 0.3(2) . . . . ?
C11 N1 C1 C2 179.37(18) . . . . ?
C11 C6 C7 C8 2.7(3) . . . . ?
C12 C2 C3 C4 -177.86(19) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C12 C17 C16 -0.7(3) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C13 C14 C15 C18 177.6(2) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C12 0.4(3) . . . . ?
C17 C12 C13 C14 0.1(3) . . . . ?
C18 C15 C16 C17 -178.2(2) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C20 C19 C24 C23 1.0(3) . . . . ?
C20 C21 C22 C23 0.9(3) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C19 -0.7(3) . . . . ?
C24 C19 C20 C21 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.487
_oxdiff_exptl_absorpt_empirical_full_min 0.765
