# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_553
_audit_block_doi                 10.5517/ccdc.csd.cc2fglj1
_database_code_depnum_ccdc_archive 'CCDC 2248353'
loop_
_audit_author_name
_audit_author_address
'li cheng'
;Xiangtan University
China
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_audit_creation_date             2023-01-06
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 Cl N2 O'
_chemical_formula_sum            'C24 H19 Cl N2 O'
_chemical_formula_weight         386.86
_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'
Cl Cl 0.3639 0.7018 '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                   11.2188(4)
_cell_length_b                   20.7777(7)
_cell_length_c                   8.8300(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.930(4)
_cell_angle_gamma                90
_cell_volume                     1935.01(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4340
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      73.2190
_cell_measurement_theta_min      2.0850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7351
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.813
_diffrn_reflns_theta_min         4.192
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00  57.00   1.00    1.00    --   40.92  37.00  30.00   27
  2  ω     39.00 131.00   1.00    1.00    --  107.58 -45.00 -60.00   92
  3  ω     71.00 109.00   1.00    1.00    --  107.58 -94.00-150.00   38
  4  ω     60.00  97.00   1.00    1.00    --  107.58 -94.00 -60.00   37
  5  ω     52.00 128.00   1.00    1.00    --  107.58 -61.00  30.00   76
  6  ω     82.00 175.00   1.00    1.00    --  107.58  30.00 120.00   93
  7  ω    140.00 177.00   1.00    1.00    --  107.58 126.00 -62.00   37
  8  ω     95.00 125.00   1.00    1.00    --  107.58 126.00 -62.00   30
  9  ω      2.00  60.00   1.00    1.00    --   40.92 -99.00 150.00   58
 10  ω     35.00  88.00   1.00    1.00    --   40.92-125.00 -30.00   53
 11  ω     27.00  52.00   1.00    1.00    --  107.58 -94.00-150.00   25
 12  ω   -113.00 -20.00   1.00    1.00    --  -40.92 -37.00 -90.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1431740000
_diffrn_orient_matrix_UB_12      0.0142735000
_diffrn_orient_matrix_UB_13      -0.0535211000
_diffrn_orient_matrix_UB_21      0.0285427000
_diffrn_orient_matrix_UB_22      0.0725702000
_diffrn_orient_matrix_UB_23      0.0227677000
_diffrn_orient_matrix_UB_31      -0.0052729000
_diffrn_orient_matrix_UB_32      0.0050566000
_diffrn_orient_matrix_UB_33      -0.1762453000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3352
_reflns_number_total             3811
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL n/a (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0017(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   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3811
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0476
_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)+(0.0806P)²+0.5660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1402
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C23(H23)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C24(H24A,H24B,H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Cl1 Cl 0.22582(6) 0.20765(3) 0.03976(10) 0.0715(2) Uani 1 1 d . . . . .
O1 O 0.41833(11) 0.43211(6) -0.02466(13) 0.0319(3) Uani 1 1 d . . . . .
H1 H 0.398457 0.465631 -0.080869 0.048 Uiso 1 1 calc R U . . .
N1 N 0.53735(12) 0.44091(6) 0.09672(15) 0.0267(3) Uani 1 1 d . . . . .
N2 N 0.72136(14) 0.32661(7) 0.37518(17) 0.0342(3) Uani 1 1 d . . . . .
C1 C 0.74365(15) 0.49303(8) 0.47927(18) 0.0295(3) Uani 1 1 d . . . . .
C2 C 0.74123(18) 0.53940(9) 0.5922(2) 0.0354(4) Uani 1 1 d . . . . .
H2 H 0.786401 0.578710 0.601298 0.042 Uiso 1 1 calc R U . . .
C3 C 0.67067(19) 0.52638(9) 0.6910(2) 0.0390(4) Uani 1 1 d . . . . .
H3 H 0.668043 0.557260 0.769131 0.047 Uiso 1 1 calc R U . . .
C4 C 0.60410(18) 0.46927(10) 0.6779(2) 0.0392(4) Uani 1 1 d . . . . .
H4 H 0.556786 0.461539 0.747138 0.047 Uiso 1 1 calc R U . . .
C5 C 0.60582(17) 0.42303(9) 0.5642(2) 0.0346(4) Uani 1 1 d . . . . .
H5 H 0.559901 0.383920 0.554268 0.042 Uiso 1 1 calc R U . . .
C6 C 0.67607(16) 0.43577(8) 0.46665(18) 0.0286(3) Uani 1 1 d . . . . .
C7 C 0.69622(15) 0.39500(7) 0.33387(18) 0.0275(3) Uani 1 1 d . . . . .
C8 C 0.79843(15) 0.43272(8) 0.29394(18) 0.0279(3) Uani 1 1 d . . . . .
C9 C 0.81577(15) 0.49046(8) 0.36709(18) 0.0288(3) Uani 1 1 d . . . . .
C10 C 0.89473(17) 0.54541(9) 0.3465(2) 0.0376(4) Uani 1 1 d . . . . .
H10A H 0.953797 0.530111 0.294335 0.056 Uiso 1 1 calc R U . . .
H10B H 0.942644 0.563541 0.452237 0.056 Uiso 1 1 calc R U . . .
H10C H 0.839560 0.578629 0.279427 0.056 Uiso 1 1 calc R U . . .
C11 C 0.86134(15) 0.40860(8) 0.18218(19) 0.0309(4) Uani 1 1 d . . . . .
C12 C 0.94182(18) 0.35555(9) 0.2231(2) 0.0379(4) Uani 1 1 d . . . . .
H12 H 0.951762 0.332749 0.319912 0.046 Uiso 1 1 calc R U . . .
C13 C 1.00771(19) 0.33566(10) 0.1237(3) 0.0453(5) Uani 1 1 d . . . . .
H13 H 1.064603 0.300312 0.154696 0.054 Uiso 1 1 calc R U . . .
C14 C 0.9909(2) 0.36697(12) -0.0196(3) 0.0525(5) Uani 1 1 d . . . . .
H14 H 1.034880 0.352894 -0.088340 0.063 Uiso 1 1 calc R U . . .
C15 C 0.9099(2) 0.41876(14) -0.0624(3) 0.0621(7) Uani 1 1 d . . . . .
H15 H 0.897523 0.440269 -0.161566 0.075 Uiso 1 1 calc R U . . .
C16 C 0.8462(2) 0.43979(12) 0.0384(2) 0.0490(5) Uani 1 1 d . . . . .
H16 H 0.791564 0.476034 0.008230 0.059 Uiso 1 1 calc R U . . .
C17 C 0.57208(15) 0.39203(7) 0.18981(18) 0.0257(3) Uani 1 1 d . . . . .
C18 C 0.51697(17) 0.32882(8) 0.19183(19) 0.0302(4) Uani 1 1 d . . . . .
C19 C 0.61000(18) 0.29226(8) 0.3070(2) 0.0337(4) Uani 1 1 d . . . . .
C20 C 0.5849(2) 0.22861(9) 0.3384(2) 0.0450(5) Uani 1 1 d . . . . .
H20 H 0.647274 0.203291 0.415084 0.054 Uiso 1 1 calc R U . . .
C21 C 0.4663(2) 0.20367(9) 0.2542(3) 0.0495(5) Uani 1 1 d . . . . .
H21 H 0.446866 0.160676 0.274020 0.059 Uiso 1 1 calc R U . . .
C22 C 0.3756(2) 0.24043(9) 0.1415(3) 0.0450(5) Uani 1 1 d . . . . .
C23 C 0.39848(19) 0.30331(8) 0.1069(2) 0.0364(4) Uani 1 1 d . . . . .
H23 H 0.335856 0.327914 0.028552 0.044 Uiso 1 1 calc R U . . .
C24 C 0.8112(2) 0.30956(11) 0.5323(2) 0.0491(5) Uani 1 1 d . . . . .
H24A H 0.880434 0.340999 0.563892 0.074 Uiso 1 1 calc R U . . .
H24B H 0.845647 0.266599 0.527110 0.074 Uiso 1 1 calc R U . . .
H24C H 0.768032 0.309574 0.611930 0.074 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 C22 1.751(2) . ?
O1 H1 0.8400 . ?
O1 N1 1.4105(17) . ?
N1 C17 1.281(2) . ?
N2 C7 1.470(2) . ?
N2 C19 1.386(2) . ?
N2 C24 1.454(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.395(2) . ?
C1 C9 1.478(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(2) . ?
C6 C7 1.524(2) . ?
C7 C8 1.526(2) . ?
C7 C17 1.534(2) . ?
C8 C9 1.345(2) . ?
C8 C11 1.483(2) . ?
C9 C10 1.494(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.392(3) . ?
C11 C16 1.384(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.375(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.454(2) . ?
C18 C19 1.406(3) . ?
C18 C23 1.389(3) . ?
C19 C20 1.399(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(3) . ?
C22 C23 1.385(3) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 H1 109.5 . . ?
C17 N1 O1 112.76(13) . . ?
C19 N2 C7 108.77(13) . . ?
C19 N2 C24 121.21(15) . . ?
C24 N2 C7 118.97(15) . . ?
C2 C1 C9 130.77(16) . . ?
C6 C1 C2 120.30(15) . . ?
C6 C1 C9 108.80(14) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 117.95(17) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.36(17) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.70(17) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 117.98(17) . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C7 108.45(14) . . ?
C5 C6 C1 121.71(16) . . ?
C5 C6 C7 129.84(16) . . ?
N2 C7 C6 114.36(12) . . ?
N2 C7 C8 117.25(13) . . ?
N2 C7 C17 102.12(13) . . ?
C6 C7 C17 109.23(12) . . ?
C8 C7 C6 102.26(13) . . ?
C8 C7 C17 111.74(12) . . ?
C9 C8 C7 110.13(13) . . ?
C9 C8 C11 126.69(15) . . ?
C11 C8 C7 123.09(14) . . ?
C1 C9 C10 122.45(15) . . ?
C8 C9 C1 109.36(14) . . ?
C8 C9 C10 128.18(15) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 120.57(15) . . ?
C16 C11 C8 121.01(16) . . ?
C16 C11 C12 118.36(16) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.61(18) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.26(19) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.56(18) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.8(2) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
N1 C17 C7 119.45(14) . . ?
N1 C17 C18 133.34(15) . . ?
C18 C17 C7 107.21(13) . . ?
C19 C18 C17 106.43(15) . . ?
C23 C18 C17 132.10(16) . . ?
C23 C18 C19 121.46(16) . . ?
N2 C19 C18 111.90(14) . . ?
N2 C19 C20 127.84(18) . . ?
C20 C19 C18 120.25(19) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 C19 118.0(2) . . ?
C21 C20 H20 121.0 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.03(17) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 Cl1 119.72(15) . . ?
C21 C22 C23 122.2(2) . . ?
C23 C22 Cl1 118.09(18) . . ?
C18 C23 H23 121.4 . . ?
C22 C23 C18 117.10(19) . . ?
C22 C23 H23 121.4 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C22 C23 C18 178.52(13) . . . . ?
O1 N1 C17 C7 -176.79(12) . . . . ?
O1 N1 C17 C18 3.1(2) . . . . ?
N1 C17 C18 C19 169.91(17) . . . . ?
N1 C17 C18 C23 -11.0(3) . . . . ?
N2 C7 C8 C9 -136.08(15) . . . . ?
N2 C7 C8 C11 47.2(2) . . . . ?
N2 C7 C17 N1 -162.74(14) . . . . ?
N2 C7 C17 C18 17.34(15) . . . . ?
N2 C19 C20 C21 -179.33(17) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C6 C7 N2 135.94(14) . . . . ?
C1 C6 C7 C8 8.15(16) . . . . ?
C1 C6 C7 C17 -110.35(15) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C2 C1 C6 C7 179.83(14) . . . . ?
C2 C1 C9 C8 172.98(17) . . . . ?
C2 C1 C9 C10 -6.4(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 179.74(16) . . . . ?
C5 C6 C7 N2 -44.0(2) . . . . ?
C5 C6 C7 C8 -171.81(17) . . . . ?
C5 C6 C7 C17 69.7(2) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C6 C1 C9 C8 -2.89(18) . . . . ?
C6 C1 C9 C10 177.72(15) . . . . ?
C6 C7 C8 C9 -10.16(17) . . . . ?
C6 C7 C8 C11 173.12(14) . . . . ?
C6 C7 C17 N1 75.82(17) . . . . ?
C6 C7 C17 C18 -104.11(14) . . . . ?
C7 N2 C19 C18 13.56(18) . . . . ?
C7 N2 C19 C20 -167.67(17) . . . . ?
C7 C8 C9 C1 8.37(18) . . . . ?
C7 C8 C9 C10 -172.28(16) . . . . ?
C7 C8 C11 C12 -67.8(2) . . . . ?
C7 C8 C11 C16 115.1(2) . . . . ?
C7 C17 C18 C19 -10.18(16) . . . . ?
C7 C17 C18 C23 168.91(17) . . . . ?
C8 C7 C17 N1 -36.59(19) . . . . ?
C8 C7 C17 C18 143.48(13) . . . . ?
C8 C11 C12 C13 -175.47(17) . . . . ?
C8 C11 C16 C15 177.0(2) . . . . ?
C9 C1 C2 C3 -175.01(17) . . . . ?
C9 C1 C6 C5 176.17(15) . . . . ?
C9 C1 C6 C7 -3.80(18) . . . . ?
C9 C8 C11 C12 116.0(2) . . . . ?
C9 C8 C11 C16 -61.1(3) . . . . ?
C11 C8 C9 C1 -175.05(15) . . . . ?
C11 C8 C9 C10 4.3(3) . . . . ?
C11 C12 C13 C14 -2.2(3) . . . . ?
C12 C11 C16 C15 -0.1(3) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C11 -1.0(4) . . . . ?
C16 C11 C12 C13 1.7(3) . . . . ?
C17 C7 C8 C9 106.56(15) . . . . ?
C17 C7 C8 C11 -70.16(19) . . . . ?
C17 C18 C19 N2 -1.73(18) . . . . ?
C17 C18 C19 C20 179.39(15) . . . . ?
C17 C18 C23 C22 -178.50(16) . . . . ?
C18 C19 C20 C21 -0.6(3) . . . . ?
C19 N2 C7 C6 99.32(16) . . . . ?
C19 N2 C7 C8 -140.98(14) . . . . ?
C19 N2 C7 C17 -18.52(16) . . . . ?
C19 C18 C23 C22 0.5(2) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 Cl1 -178.97(15) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C18 -0.7(3) . . . . ?
C23 C18 C19 N2 179.06(14) . . . . ?
C23 C18 C19 C20 0.2(2) . . . . ?
C24 N2 C7 C6 -45.1(2) . . . . ?
C24 N2 C7 C8 74.6(2) . . . . ?
C24 N2 C7 C17 -162.98(15) . . . . ?
C24 N2 C19 C18 157.08(16) . . . . ?
C24 N2 C19 C20 -24.2(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 1.537
_oxdiff_exptl_absorpt_empirical_full_min 0.527
####################################################################### 
# 
# 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_458-2
_database_code_depnum_ccdc_archive 'CCDC 2248355'
loop_
_audit_author_name
_audit_author_address
'li cheng'
;Xiangtan University
China
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_audit_creation_date             2022-12-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H22 N2 O'
_chemical_formula_sum            'C31 H22 N2 O'
_chemical_formula_weight         438.50
_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                   10.2696(12)
_cell_length_b                   10.3708(13)
_cell_length_c                   12.6585(13)
_cell_angle_alpha                90.132(9)
_cell_angle_beta                 110.122(10)
_cell_angle_gamma                104.018(10)
_cell_volume                     1222.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3121
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      28.1930
_cell_measurement_theta_min      2.5520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8691
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.187
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  61.00   1.00    5.00    --  -11.27  77.00 120.00  105
  2  ω     28.00  56.00   1.00    5.00    --  -11.27  77.00   0.00   28
  3  ω      1.00  77.00   1.00    5.00    --   11.90  77.00  30.00   76
  4  ω    -20.00  86.00   1.00    5.00    --   11.90  77.00 -90.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0274119000
_diffrn_orient_matrix_UB_12      -0.0530444000
_diffrn_orient_matrix_UB_13      -0.0110348000
_diffrn_orient_matrix_UB_21      0.0431653000
_diffrn_orient_matrix_UB_22      0.0436808000
_diffrn_orient_matrix_UB_23      -0.0251123000
_diffrn_orient_matrix_UB_31      0.0564309000
_diffrn_orient_matrix_UB_32      0.0170840000
_diffrn_orient_matrix_UB_33      0.0532967000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3009
_reflns_number_total             4303
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0653
_refine_ls_restrained_S_all      1.092
_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)+(0.0962P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.1861
_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. Restrained distances
 O1-H1
 0.82 with sigma of 0.01
 N2-C13
 2.6 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.99774(18) 0.99380(16) 0.36451(15) 0.0452(5) Uani 1 1 d D . . . .
N1 N 0.7385(2) 0.56147(16) 0.30581(15) 0.0350(5) Uani 1 1 d . . . . .
N2 N 0.92004(19) 0.89575(17) 0.41165(16) 0.0365(5) Uani 1 1 d D . . . .
C1 C 0.3986(3) 0.8025(2) 0.06480(19) 0.0400(6) Uani 1 1 d . . . . .
C2 C 0.4705(3) 0.8196(2) -0.0115(2) 0.0516(7) Uani 1 1 d . . . . .
H2 H 0.563083 0.804057 0.009234 0.062 Uiso 1 1 calc R U . . .
C3 C 0.4080(4) 0.8590(3) -0.1169(2) 0.0684(9) Uani 1 1 d . . . . .
H3 H 0.458409 0.871243 -0.168022 0.082 Uiso 1 1 calc R U . . .
C4 C 0.2752(4) 0.8804(3) -0.1483(3) 0.0777(11) Uani 1 1 d . . . . .
H4 H 0.233215 0.907955 -0.221036 0.093 Uiso 1 1 calc R U . . .
C5 C 0.2019(4) 0.8624(3) -0.0755(3) 0.0809(11) Uani 1 1 d . . . . .
H5 H 0.108300 0.875950 -0.098237 0.097 Uiso 1 1 calc R U . . .
C6 C 0.2637(3) 0.8242(3) 0.0323(2) 0.0611(8) Uani 1 1 d . . . . .
H6 H 0.212869 0.813267 0.083090 0.073 Uiso 1 1 calc R U . . .
C7 C 0.4671(2) 0.7662(2) 0.1744(2) 0.0372(6) Uani 1 1 d . . . . .
C8 C 0.5313(2) 0.7412(2) 0.2680(2) 0.0342(5) Uani 1 1 d . . . . .
C9 C 0.6189(2) 0.71224(19) 0.37383(18) 0.0312(5) Uani 1 1 d . . . . .
C10 C 0.6045(2) 0.7210(2) 0.47624(18) 0.0314(5) Uani 1 1 d . . . . .
C11 C 0.7256(2) 0.6838(2) 0.56104(18) 0.0327(5) Uani 1 1 d . . . . .
C12 C 0.8172(2) 0.6561(2) 0.50881(18) 0.0317(5) Uani 1 1 d . . . . .
C13 C 0.7585(2) 0.6751(2) 0.38454(18) 0.0313(5) Uani 1 1 d D . . . .
C14 C 0.8546(2) 0.7888(2) 0.34532(18) 0.0319(5) Uani 1 1 d . . . . .
C15 C 0.8462(2) 0.7436(2) 0.23343(19) 0.0352(6) Uani 1 1 d . . . . .
C16 C 0.7703(2) 0.6086(2) 0.2126(2) 0.0365(6) Uani 1 1 d . . . . .
C17 C 0.7386(3) 0.5372(3) 0.1100(2) 0.0480(7) Uani 1 1 d . . . . .
H17 H 0.685539 0.446204 0.094890 0.058 Uiso 1 1 calc R U . . .
C18 C 0.7870(3) 0.6034(3) 0.0309(2) 0.0604(8) Uani 1 1 d . . . . .
H18 H 0.765330 0.556941 -0.040270 0.072 Uiso 1 1 calc R U . . .
C19 C 0.8660(3) 0.7353(3) 0.0519(2) 0.0615(8) Uani 1 1 d . . . . .
H19 H 0.899084 0.776924 -0.004170 0.074 Uiso 1 1 calc R U . . .
C20 C 0.8974(3) 0.8076(3) 0.1540(2) 0.0480(7) Uani 1 1 d . . . . .
H20 H 0.952330 0.897990 0.169056 0.058 Uiso 1 1 calc R U . . .
C21 C 0.6259(3) 0.4423(2) 0.2956(2) 0.0478(7) Uani 1 1 d . . . . .
H21A H 0.533806 0.454805 0.245488 0.072 Uiso 1 1 calc R U . . .
H21B H 0.620980 0.424651 0.370328 0.072 Uiso 1 1 calc R U . . .
H21C H 0.646426 0.366418 0.263952 0.072 Uiso 1 1 calc R U . . .
C22 C 0.9399(2) 0.6197(2) 0.5692(2) 0.0403(6) Uani 1 1 d . . . . .
H22 H 1.002591 0.603314 0.533269 0.048 Uiso 1 1 calc R U . . .
C23 C 0.9706(3) 0.6072(2) 0.6841(2) 0.0470(6) Uani 1 1 d . . . . .
H23 H 1.054906 0.581742 0.727108 0.056 Uiso 1 1 calc R U . . .
C24 C 0.8797(3) 0.6313(2) 0.7361(2) 0.0469(6) Uani 1 1 d . . . . .
H24 H 0.901377 0.620535 0.814316 0.056 Uiso 1 1 calc R U . . .
C25 C 0.7568(3) 0.6713(2) 0.6760(2) 0.0405(6) Uani 1 1 d . . . . .
H25 H 0.695683 0.689587 0.712629 0.049 Uiso 1 1 calc R U . . .
C26 C 0.4912(2) 0.7667(2) 0.49918(18) 0.0332(5) Uani 1 1 d . . . . .
C27 C 0.5269(3) 0.8642(2) 0.5877(2) 0.0403(6) Uani 1 1 d . . . . .
H27 H 0.624126 0.896784 0.636416 0.048 Uiso 1 1 calc R U . . .
C28 C 0.4219(3) 0.9136(2) 0.6049(2) 0.0507(7) Uani 1 1 d . . . . .
H28 H 0.447411 0.981330 0.664476 0.061 Uiso 1 1 calc R U . . .
C29 C 0.2803(3) 0.8656(3) 0.5364(3) 0.0589(8) Uani 1 1 d . . . . .
H29 H 0.208348 0.898958 0.549548 0.071 Uiso 1 1 calc R U . . .
C30 C 0.2430(3) 0.7691(3) 0.4488(2) 0.0558(7) Uani 1 1 d . . . . .
H30 H 0.145374 0.736320 0.401101 0.067 Uiso 1 1 calc R U . . .
C31 C 0.3482(3) 0.7199(2) 0.4302(2) 0.0426(6) Uani 1 1 d . . . . .
H31 H 0.322019 0.653402 0.369604 0.051 Uiso 1 1 calc R U . . .
H1 H 1.050(3) 1.045(3) 0.4228(18) 0.086(11) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.401(2) . ?
O1 H1 0.839(10) . ?
N1 C13 1.470(3) . ?
N1 C16 1.388(3) . ?
N1 C21 1.444(3) . ?
N2 C14 1.278(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.377(4) . ?
C1 C7 1.421(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.357(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.205(3) . ?
C8 C9 1.414(3) . ?
C9 C10 1.360(3) . ?
C9 C13 1.535(3) . ?
C10 C11 1.471(3) . ?
C10 C26 1.470(3) . ?
C11 C12 1.401(3) . ?
C11 C25 1.392(3) . ?
C12 C13 1.511(3) . ?
C12 C22 1.373(3) . ?
C13 C14 1.545(3) . ?
C14 C15 1.458(3) . ?
C15 C16 1.401(3) . ?
C15 C20 1.388(3) . ?
C16 C17 1.389(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.392(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.392(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.395(3) . ?
C26 C31 1.387(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.380(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.376(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.376(4) . ?
C30 H30 0.9500 . ?
C30 C31 1.387(4) . ?
C31 H31 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O1 H1 100(2) . . ?
C16 N1 C13 109.33(16) . . ?
C16 N1 C21 121.67(18) . . ?
C21 N1 C13 118.83(17) . . ?
C14 N2 O1 112.66(18) . . ?
C2 C1 C7 119.3(2) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 C7 121.9(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.9(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C1 176.5(2) . . ?
C7 C8 C9 173.9(2) . . ?
C8 C9 C13 119.64(18) . . ?
C10 C9 C8 129.2(2) . . ?
C10 C9 C13 111.01(19) . . ?
C9 C10 C11 108.42(19) . . ?
C9 C10 C26 125.7(2) . . ?
C26 C10 C11 125.81(19) . . ?
C12 C11 C10 109.31(18) . . ?
C25 C11 C10 130.9(2) . . ?
C25 C11 C12 119.8(2) . . ?
C11 C12 C13 109.34(19) . . ?
C22 C12 C11 121.4(2) . . ?
C22 C12 C13 129.2(2) . . ?
N1 C13 C9 113.90(17) . . ?
N1 C13 C12 116.02(17) . . ?
N1 C13 C14 101.50(16) . . ?
C9 C13 C14 109.09(17) . . ?
C12 C13 C9 101.82(16) . . ?
C12 C13 C14 114.81(17) . . ?
N2 C14 C13 117.95(19) . . ?
N2 C14 C15 134.7(2) . . ?
C15 C14 C13 107.34(17) . . ?
C16 C15 C14 106.67(18) . . ?
C20 C15 C14 132.6(2) . . ?
C20 C15 C16 120.8(2) . . ?
N1 C16 C15 111.59(19) . . ?
C17 C16 N1 127.5(2) . . ?
C17 C16 C15 120.9(2) . . ?
C16 C17 H17 121.3 . . ?
C18 C17 C16 117.5(2) . . ?
C18 C17 H17 121.3 . . ?
C17 C18 H18 118.9 . . ?
C17 C18 C19 122.1(2) . . ?
C19 C18 H18 118.9 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.7(2) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 117.9(2) . . ?
C15 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C22 H22 120.7 . . ?
C12 C22 C23 118.5(2) . . ?
C23 C22 H22 120.7 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.1(2) . . ?
C25 C24 H24 119.4 . . ?
C11 C25 C24 118.5(2) . . ?
C11 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?
C27 C26 C10 120.2(2) . . ?
C31 C26 C10 121.17(19) . . ?
C31 C26 C27 118.6(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(2) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.5(2) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.0(2) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.9(3) . . ?
C31 C30 H30 120.1 . . ?
C26 C31 C30 120.8(2) . . ?
C26 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?

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 N2 C14 C13 -176.91(18) . . . . ?
O1 N2 C14 C15 2.5(4) . . . . ?
N1 C13 C14 N2 -164.28(19) . . . . ?
N1 C13 C14 C15 16.1(2) . . . . ?
N1 C16 C17 C18 -176.9(2) . . . . ?
N2 C14 C15 C16 172.5(2) . . . . ?
N2 C14 C15 C20 -7.0(5) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C7 C1 C2 C3 -177.9(2) . . . . ?
C7 C1 C6 C5 178.7(2) . . . . ?
C8 C9 C10 C11 -178.27(19) . . . . ?
C8 C9 C10 C26 -1.2(3) . . . . ?
C8 C9 C13 N1 -55.5(2) . . . . ?
C8 C9 C13 C12 178.80(17) . . . . ?
C8 C9 C13 C14 57.1(2) . . . . ?
C9 C10 C11 C12 1.9(2) . . . . ?
C9 C10 C11 C25 -176.9(2) . . . . ?
C9 C10 C26 C27 -129.8(2) . . . . ?
C9 C10 C26 C31 46.6(3) . . . . ?
C9 C13 C14 N2 75.2(2) . . . . ?
C9 C13 C14 C15 -104.39(19) . . . . ?
C10 C9 C13 N1 128.89(19) . . . . ?
C10 C9 C13 C12 3.2(2) . . . . ?
C10 C9 C13 C14 -118.5(2) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C10 C11 C12 C22 179.49(18) . . . . ?
C10 C11 C25 C24 178.8(2) . . . . ?
C10 C26 C27 C28 175.7(2) . . . . ?
C10 C26 C31 C30 -176.3(2) . . . . ?
C11 C10 C26 C27 46.8(3) . . . . ?
C11 C10 C26 C31 -136.8(2) . . . . ?
C11 C12 C13 N1 -126.22(19) . . . . ?
C11 C12 C13 C9 -2.0(2) . . . . ?
C11 C12 C13 C14 115.7(2) . . . . ?
C11 C12 C22 C23 1.6(3) . . . . ?
C12 C11 C25 C24 0.1(3) . . . . ?
C12 C13 C14 N2 -38.3(3) . . . . ?
C12 C13 C14 C15 142.11(19) . . . . ?
C12 C22 C23 C24 -0.2(3) . . . . ?
C13 N1 C16 C15 15.5(3) . . . . ?
C13 N1 C16 C17 -166.1(2) . . . . ?
C13 C9 C10 C11 -3.2(2) . . . . ?
C13 C9 C10 C26 173.87(18) . . . . ?
C13 C12 C22 C23 -179.30(19) . . . . ?
C13 C14 C15 C16 -8.0(2) . . . . ?
C13 C14 C15 C20 172.5(3) . . . . ?
C14 C15 C16 N1 -4.3(3) . . . . ?
C14 C15 C16 C17 177.3(2) . . . . ?
C14 C15 C20 C19 -177.9(3) . . . . ?
C15 C16 C17 C18 1.3(4) . . . . ?
C16 N1 C13 C9 98.2(2) . . . . ?
C16 N1 C13 C12 -144.08(19) . . . . ?
C16 N1 C13 C14 -18.9(2) . . . . ?
C16 C15 C20 C19 2.7(4) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C17 C18 C19 C20 -1.3(5) . . . . ?
C18 C19 C20 C15 -0.5(4) . . . . ?
C20 C15 C16 N1 175.3(2) . . . . ?
C20 C15 C16 C17 -3.1(4) . . . . ?
C21 N1 C13 C9 -47.8(3) . . . . ?
C21 N1 C13 C12 70.0(3) . . . . ?
C21 N1 C13 C14 -164.84(19) . . . . ?
C21 N1 C16 C15 160.3(2) . . . . ?
C21 N1 C16 C17 -21.4(4) . . . . ?
C22 C12 C13 N1 54.6(3) . . . . ?
C22 C12 C13 C9 178.9(2) . . . . ?
C22 C12 C13 C14 -63.4(3) . . . . ?
C22 C23 C24 C25 -1.3(4) . . . . ?
C23 C24 C25 C11 1.3(3) . . . . ?
C25 C11 C12 C13 179.19(18) . . . . ?
C25 C11 C12 C22 -1.6(3) . . . . ?
C26 C10 C11 C12 -175.20(19) . . . . ?
C26 C10 C11 C25 6.0(4) . . . . ?
C26 C27 C28 C29 1.2(4) . . . . ?
C27 C26 C31 C30 0.1(3) . . . . ?
C27 C28 C29 C30 -1.1(4) . . . . ?
C28 C29 C30 C31 0.4(4) . . . . ?
C29 C30 C31 C26 0.1(4) . . . . ?
C31 C26 C27 C28 -0.7(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 7.771
_oxdiff_exptl_absorpt_empirical_full_min 0.238
