# Supplementary Information (SI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

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

data_ywd_1_2
_audit_block_doi                 10.5517/ccdc.csd.cc26t6js
_database_code_depnum_ccdc_archive 'CCDC 2050015'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0QM01047B 2021
loop_
_audit_author_name
_audit_author_address
'Hengchang Ma'
;Northwest Normal University
China
;
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2024-09-05 downloaded from the CCDC.
;
_audit_creation_date             2020-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C37 H29 N2 O'
_chemical_formula_sum            'C37 H29 Br N2 O'
_chemical_formula_weight         597.53
_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'
Br Br -0.6763 1.2805 '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/a 1'
_space_group_name_Hall           '-P 2yab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   9.1969(3)
_cell_length_b                   17.9586(4)
_cell_length_c                   20.7468(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.438(3)
_cell_angle_gamma                90
_cell_volume                     3369.92(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5448
_cell_measurement_temperature    293.65(10)
_cell_measurement_theta_max      69.3060
_cell_measurement_theta_min      5.3660
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    1.875
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60249
_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            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23382
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.890
_diffrn_reflns_theta_min         4.334
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.65(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  96.00   1.00    3.00    --   54.00 -99.00  90.00   74
  2  ω     65.00 119.00   1.00    6.00    --  108.00 -50.00  30.00   54
  3  ω     89.00 141.00   1.00    6.00    --  108.00 -91.00   0.00   52
  4  ω     65.00 114.00   1.00    6.00    --  108.00-111.00   0.00   49
  5  ω     42.00 111.00   1.00    6.00    --  108.00 -38.00 -30.00   69
  6  ω     88.00 177.00   1.00    6.00    --  108.00  25.00 -60.00   89
  7  ω    144.00 170.00   1.00    6.00    --  108.00 111.00-180.00   26
  8  ω     94.00 173.00   1.00    6.00    --  108.00 147.00 -78.00   79
  9  ω    108.00 162.00   1.00    6.00    --  108.00 111.00  60.00   54
 10  ω    101.00 162.00   1.00    6.00    --  108.00 111.00  30.00   61
 11  ω     88.00 160.00   1.00    6.00    --  108.00  38.00  30.00   72
 12  ω     86.00 127.00   1.00    6.00    --  108.00  50.00-120.00   41
 13  ω     78.00 172.00   1.00    6.00    --  108.00  77.00 -30.00   94
 14  ω     82.00 131.00   1.00    6.00    --  108.00  77.00  90.00   49
 15  ω     61.00 113.00   1.00    3.00    --   54.00  57.00  60.00   52
 16  ω     48.00 123.00   1.00    3.00    --   54.00  57.00 -30.00   75
 17  ω     41.00  69.00   1.00    1.50    --    0.00  57.00 -60.00   28
 18  ω    -15.00  17.00   1.00    3.00    --   54.00 -57.00  60.00   32
 19  ω    -13.00  78.00   1.00    3.00    --   54.00 -77.00 -60.00   91
 20  ω     50.00 146.00   1.00    6.00    --  108.00 -91.00-150.00   96
 21  ω     33.00 123.00   1.00    3.00    --   54.00  57.00-150.00   90
 22  ω      0.00  36.00   1.00    1.50    --    0.00  57.00 -60.00   36
 23  ω    -43.00  73.00   1.00    1.50    --    0.00  19.00-180.00  116
 24  ω    -14.00  69.00   1.00    3.00    --   54.00 -57.00-180.00   83
 25  ω    -51.00 -26.00   1.00    1.50    --    0.00 135.00-159.00   25
 26  ω     63.00 134.00   1.00    6.00    --  108.00 178.00 120.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0319086000
_diffrn_orient_matrix_UB_12      -0.0192196000
_diffrn_orient_matrix_UB_13      -0.0735875000
_diffrn_orient_matrix_UB_21      -0.0068276000
_diffrn_orient_matrix_UB_22      -0.0832844000
_diffrn_orient_matrix_UB_23      0.0169392000
_diffrn_orient_matrix_UB_31      -0.1671639000
_diffrn_orient_matrix_UB_32      0.0070942000
_diffrn_orient_matrix_UB_33      -0.0005329000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                4273
_reflns_number_total             6295
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.803
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0656
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1179P)²+0.9810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1980
_refine_ls_wR_factor_ref         0.2194
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33), C34(H34),
 C35(H35), C36(H36), C37(H37)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Br1 Br 0.34492(9) 0.52967(4) 0.88959(4) 0.1271(3) Uani 1 1 d . . . . .
O1 O 0.6804(3) 0.29934(13) 1.34842(13) 0.0666(6) Uani 1 1 d . . . . .
N1 N 0.9420(3) 0.24699(16) 1.05449(12) 0.0583(7) Uani 1 1 d . . . . .
N2 N 0.3511(3) 0.30982(13) 0.69640(13) 0.0540(6) Uani 1 1 d . . . . .
C1 C 0.7519(3) 0.17903(16) 1.38422(14) 0.0466(6) Uani 1 1 d . . . . .
C2 C 0.6324(4) 0.16680(19) 1.41594(16) 0.0557(7) Uani 1 1 d . . . . .
H2 H 0.547834 0.195929 1.405289 0.067 Uiso 1 1 calc R . . . .
C3 C 0.6385(4) 0.11200(19) 1.46284(17) 0.0616(8) Uani 1 1 d . . . . .
H3 H 0.557703 0.103595 1.483101 0.074 Uiso 1 1 calc R . . . .
C4 C 0.7649(4) 0.06962(19) 1.47965(17) 0.0639(9) Uani 1 1 d . . . . .
H4 H 0.769655 0.032967 1.511635 0.077 Uiso 1 1 calc R . . . .
C5 C 0.8846(4) 0.0816(2) 1.44892(19) 0.0676(9) Uani 1 1 d . . . . .
H5 H 0.969724 0.053086 1.460401 0.081 Uiso 1 1 calc R . . . .
C6 C 0.8779(4) 0.13603(18) 1.40118(16) 0.0545(7) Uani 1 1 d . . . . .
H6 H 0.958267 0.143689 1.380458 0.065 Uiso 1 1 calc R . . . .
C7 C 0.7454(3) 0.24293(16) 1.33775(15) 0.0490(7) Uani 1 1 d . . . . .
C8 C 0.8229(3) 0.23938(16) 1.28047(14) 0.0484(7) Uani 1 1 d . . . . .
C9 C 0.8614(4) 0.30575(18) 1.25397(16) 0.0574(8) Uani 1 1 d . . . . .
H9 H 0.837267 0.350854 1.271391 0.069 Uiso 1 1 calc R . . . .
C10 C 0.9353(4) 0.30504(19) 1.20185(16) 0.0598(8) Uani 1 1 d . . . . .
H10 H 0.961859 0.349876 1.184774 0.072 Uiso 1 1 calc R . . . .
C11 C 0.9704(4) 0.23905(19) 1.17466(15) 0.0539(7) Uani 1 1 d . . . . .
C12 C 0.9277(4) 0.17256(18) 1.19963(15) 0.0582(8) Uani 1 1 d . . . . .
H12 H 0.948686 0.127635 1.180971 0.070 Uiso 1 1 calc R . . . .
C13 C 0.8542(4) 0.17273(17) 1.25212(15) 0.0544(7) Uani 1 1 d . . . . .
H13 H 0.825632 0.127917 1.268506 0.065 Uiso 1 1 calc R . . . .
C14 C 1.0505(4) 0.2388(2) 1.11731(16) 0.0641(9) Uani 1 1 d . . . . .
H14A H 1.120941 0.279531 1.121731 0.077 Uiso 1 1 calc R . . . .
H14B H 1.104663 0.192533 1.116777 0.077 Uiso 1 1 calc R . . . .
C15 C 0.8970(5) 0.3150(2) 1.03328(18) 0.0703(10) Uani 1 1 d . . . . .
H15 H 0.937019 0.356840 1.056326 0.084 Uiso 1 1 calc R . . . .
C16 C 0.7919(5) 0.3232(2) 0.97764(17) 0.0673(9) Uani 1 1 d . . . . .
H16 H 0.760456 0.370848 0.964029 0.081 Uiso 1 1 calc R . . . .
C17 C 0.7314(4) 0.26237(18) 0.94120(15) 0.0547(7) Uani 1 1 d . . . . .
C18 C 0.7806(4) 0.1926(2) 0.96551(17) 0.0644(9) Uani 1 1 d . . . . .
H18 H 0.742074 0.149770 0.943684 0.077 Uiso 1 1 calc R . . . .
C19 C 0.8860(4) 0.1868(2) 1.02167(17) 0.0656(9) Uani 1 1 d . . . . .
H19 H 0.918645 0.139911 1.036921 0.079 Uiso 1 1 calc R . . . .
C20 C 0.6253(4) 0.27204(18) 0.88000(14) 0.0525(7) Uani 1 1 d . . . . .
C21 C 0.5421(4) 0.33705(17) 0.86722(15) 0.0550(7) Uani 1 1 d . . . . .
H21 H 0.550053 0.373627 0.899403 0.066 Uiso 1 1 calc R . . . .
C22 C 0.4490(3) 0.34857(17) 0.80859(15) 0.0526(7) Uani 1 1 d . . . . .
H22 H 0.392339 0.391740 0.802394 0.063 Uiso 1 1 calc R . . . .
C23 C 0.4379(3) 0.29614(16) 0.75778(15) 0.0496(7) Uani 1 1 d . . . . .
C24 C 0.5177(4) 0.23010(17) 0.77116(15) 0.0546(7) Uani 1 1 d . . . . .
H24 H 0.510188 0.193592 0.738937 0.066 Uiso 1 1 calc R . . . .
C25 C 0.6071(4) 0.21777(18) 0.83076(16) 0.0567(8) Uani 1 1 d . . . . .
H25 H 0.656435 0.172547 0.838558 0.068 Uiso 1 1 calc R . . . .
C26 C 0.2993(3) 0.38291(16) 0.67653(14) 0.0490(7) Uani 1 1 d . . . . .
C27 C 0.3940(4) 0.44409(18) 0.68715(17) 0.0579(8) Uani 1 1 d . . . . .
H27 H 0.492240 0.437830 0.707106 0.069 Uiso 1 1 calc R . . . .
C28 C 0.3409(4) 0.51390(18) 0.66786(18) 0.0646(9) Uani 1 1 d . . . . .
H28 H 0.403615 0.554812 0.675553 0.078 Uiso 1 1 calc R . . . .
C29 C 0.1959(4) 0.52400(17) 0.63726(17) 0.0620(9) Uani 1 1 d . . . . .
H29 H 0.160526 0.571286 0.624600 0.074 Uiso 1 1 calc R . . . .
C30 C 0.1050(4) 0.46321(18) 0.62588(17) 0.0585(8) Uani 1 1 d . . . . .
H30 H 0.007623 0.469271 0.604709 0.070 Uiso 1 1 calc R . . . .
C31 C 0.1562(4) 0.39302(17) 0.64543(16) 0.0532(7) Uani 1 1 d . . . . .
H31 H 0.093012 0.352308 0.637411 0.064 Uiso 1 1 calc R . . . .
C32 C 0.3187(4) 0.25212(16) 0.64816(15) 0.0514(7) Uani 1 1 d . . . . .
C33 C 0.3562(4) 0.26348(19) 0.58701(17) 0.0649(9) Uani 1 1 d . . . . .
H33 H 0.402668 0.307385 0.578268 0.078 Uiso 1 1 calc R . . . .
C34 C 0.3248(5) 0.2100(2) 0.53979(19) 0.0824(13) Uani 1 1 d . . . . .
H34 H 0.348830 0.218141 0.498708 0.099 Uiso 1 1 calc R . . . .
C35 C 0.2581(5) 0.1442(2) 0.5521(2) 0.0831(13) Uani 1 1 d . . . . .
H35 H 0.236015 0.108316 0.519482 0.100 Uiso 1 1 calc R . . . .
C36 C 0.2246(5) 0.1323(2) 0.6132(3) 0.0848(13) Uani 1 1 d . . . . .
H36 H 0.182851 0.087256 0.622426 0.102 Uiso 1 1 calc R . . . .
C37 C 0.2525(4) 0.18682(19) 0.6611(2) 0.0651(9) Uani 1 1 d . . . . .
H37 H 0.226482 0.179118 0.701867 0.078 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.217(4) . ?
N1 C14 1.498(4) . ?
N1 C15 1.338(5) . ?
N1 C19 1.330(5) . ?
N2 C23 1.397(4) . ?
N2 C26 1.431(4) . ?
N2 C32 1.434(4) . ?
C1 C2 1.397(4) . ?
C1 C6 1.384(4) . ?
C1 C7 1.493(4) . ?
C2 C3 1.378(5) . ?
C3 C4 1.380(5) . ?
C4 C5 1.386(5) . ?
C5 C6 1.385(5) . ?
C7 C8 1.494(4) . ?
C8 C9 1.385(4) . ?
C8 C13 1.387(4) . ?
C9 C10 1.378(5) . ?
C10 C11 1.376(5) . ?
C11 C12 1.386(5) . ?
C11 C14 1.509(5) . ?
C12 C13 1.382(5) . ?
C15 C16 1.373(5) . ?
C16 C17 1.387(5) . ?
C17 C18 1.395(5) . ?
C17 C20 1.465(4) . ?
C18 C19 1.378(5) . ?
C20 C21 1.395(4) . ?
C20 C25 1.400(4) . ?
C21 C22 1.371(4) . ?
C22 C23 1.403(4) . ?
C23 C24 1.396(4) . ?
C24 C25 1.373(5) . ?
C26 C27 1.395(4) . ?
C26 C31 1.369(4) . ?
C27 C28 1.378(5) . ?
C28 C29 1.381(5) . ?
C29 C30 1.369(5) . ?
C30 C31 1.381(4) . ?
C32 C33 1.389(5) . ?
C32 C37 1.370(5) . ?
C33 C34 1.365(5) . ?
C34 C35 1.376(7) . ?
C35 C36 1.374(7) . ?
C36 C37 1.386(5) . ?

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
C15 N1 C14 119.6(3) . . ?
C19 N1 C14 120.0(3) . . ?
C19 N1 C15 120.3(3) . . ?
C23 N2 C26 122.0(2) . . ?
C23 N2 C32 121.4(2) . . ?
C26 N2 C32 116.4(2) . . ?
C2 C1 C7 118.8(3) . . ?
C6 C1 C2 119.1(3) . . ?
C6 C1 C7 121.8(3) . . ?
C3 C2 C1 120.7(3) . . ?
C2 C3 C4 119.8(3) . . ?
C3 C4 C5 120.1(3) . . ?
C6 C5 C4 120.2(3) . . ?
C1 C6 C5 120.1(3) . . ?
O1 C7 C1 119.1(3) . . ?
O1 C7 C8 120.1(3) . . ?
C1 C7 C8 120.8(3) . . ?
C9 C8 C7 118.2(3) . . ?
C9 C8 C13 119.1(3) . . ?
C13 C8 C7 122.7(3) . . ?
C10 C9 C8 120.1(3) . . ?
C11 C10 C9 121.0(3) . . ?
C10 C11 C12 119.0(3) . . ?
C10 C11 C14 120.7(3) . . ?
C12 C11 C14 120.3(3) . . ?
C13 C12 C11 120.3(3) . . ?
C12 C13 C8 120.3(3) . . ?
N1 C14 C11 110.0(3) . . ?
N1 C15 C16 120.2(3) . . ?
C15 C16 C17 121.7(3) . . ?
C16 C17 C18 116.0(3) . . ?
C16 C17 C20 121.2(3) . . ?
C18 C17 C20 122.8(3) . . ?
C19 C18 C17 120.4(3) . . ?
N1 C19 C18 121.3(3) . . ?
C21 C20 C17 121.4(3) . . ?
C21 C20 C25 117.1(3) . . ?
C25 C20 C17 121.5(3) . . ?
C22 C21 C20 121.9(3) . . ?
C21 C22 C23 120.9(3) . . ?
N2 C23 C22 121.2(3) . . ?
C24 C23 N2 121.6(3) . . ?
C24 C23 C22 117.2(3) . . ?
C25 C24 C23 121.6(3) . . ?
C24 C25 C20 121.2(3) . . ?
C27 C26 N2 120.7(3) . . ?
C31 C26 N2 119.9(3) . . ?
C31 C26 C27 119.3(3) . . ?
C28 C27 C26 119.5(3) . . ?
C27 C28 C29 121.0(3) . . ?
C30 C29 C28 118.9(3) . . ?
C29 C30 C31 120.8(3) . . ?
C26 C31 C30 120.5(3) . . ?
C33 C32 N2 118.5(3) . . ?
C37 C32 N2 121.7(3) . . ?
C37 C32 C33 119.8(3) . . ?
C34 C33 C32 119.8(4) . . ?
C33 C34 C35 121.0(4) . . ?
C36 C35 C34 119.1(4) . . ?
C35 C36 C37 120.5(4) . . ?
C32 C37 C36 119.7(4) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.500 0.000 0.000 333.6 76.7 ?
2 0.000 0.500 1.000 333.6 76.7 ?

_olex2_date_sample_data_collection 2020-12-02
_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 1.994
_oxdiff_exptl_absorpt_empirical_full_min 0.641
####################################################################### 
# 
# 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_caoyasong_2_auto
_database_code_depnum_ccdc_archive 'CCDC 2363480'
loop_
_audit_author_name
_audit_author_address
'haowen Huang'
;Northwest Normal University
China
;
_audit_update_record             
;
2024-06-18 deposited with the CCDC.	2024-09-05 downloaded from the CCDC.
;
_audit_creation_date             2024-03-03
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        m-TPA-Pyr-BP
_chemical_formula_moiety         'Br, C37 H29 N2 O, H2 O'
_chemical_formula_sum            'C37 H31 Br N2 O2'
_chemical_formula_weight         615.55
_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'
Br Br -0.6763 1.2805 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.1563(2)
_cell_length_b                   9.88830(10)
_cell_length_c                   39.4971(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5919.43(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12759
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.3100
_cell_measurement_theta_min      2.2370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            23919
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.724
_diffrn_reflns_theta_min         2.237
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00   0.00   0.50    1.00    --  -45.05  44.00  13.00   98
  2  ω     14.00  58.00   0.50    1.00    --   45.05-113.00 145.00   88
  3  ω    -93.00 -68.00   0.50    4.00    -- -100.00 113.00-122.00   50
  4  ω     39.00 113.00   0.50    4.00    --  112.00 -80.00  33.00  148
  5  ω    138.00 174.00   0.50    4.00    --  112.00  44.00  13.00   72
  6  ω    -25.00   6.00   0.50    1.00    --   45.05 -19.00-120.00   62
  7  ω    -33.00  19.00   0.50    1.00    --   45.05 -19.00 -30.00  104
  8  ω    -54.00 -29.00   0.50    4.00    -- -100.00  45.00 120.00   50
  9  ω     40.00  65.00   0.50    4.00    --  112.00 -61.00 120.00   50
 10  ω     47.00 105.00   0.50    4.00    --  112.00-125.00 -60.00  116
 11  ω     55.00 112.00   0.50    4.00    --  112.00-125.00 -90.00  114
 12  ω     65.00 108.00   0.50    4.00    --  112.00-125.00-120.00   86
 13  ω     99.00 158.00   0.50    4.00    --  112.00  45.00 -30.00  118
 14  ω     99.00 127.00   0.50    4.00    --  112.00  61.00 150.00   56
 15  ω    141.00 174.00   0.50    4.00    --  112.00  61.00 150.00   66
 16  ω     40.00  65.00   0.50    4.00    --  112.00 -61.00  90.00   50
 17  ω     42.00  83.00   0.50    4.00    --  112.00 -77.00  90.00   82
 18  ω     41.00  68.00   0.50    4.00    --  112.00 -61.00-150.00   54
 19  ω     39.00  65.00   0.50    4.00    --  112.00 -61.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0267272000
_diffrn_orient_matrix_UB_12      -0.0119671000
_diffrn_orient_matrix_UB_13      0.0375016000
_diffrn_orient_matrix_UB_21      -0.0489905000
_diffrn_orient_matrix_UB_22      0.1328353000
_diffrn_orient_matrix_UB_23      0.0077995000
_diffrn_orient_matrix_UB_31      -0.0849801000
_diffrn_orient_matrix_UB_32      -0.0805093000
_diffrn_orient_matrix_UB_33      0.0073267000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5572
_reflns_number_total             6173
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+6.7929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1041
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O2(H2A,H2B)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23), C26(H26), C27(H27), C29(H29), C30(H30), C33(H33), C34(H34),
 C35(H35), C36(H36), C37(H37)
;
_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
Br1 Br 0.52050(2) 0.83002(2) 0.21837(2) 0.03184(9) Uani 1 1 d . . . . .
O1 O 0.38068(13) -0.02111(18) 0.10870(5) 0.0441(4) Uani 1 1 d . . . . .
N1 N 0.33135(12) 0.52650(18) 0.22947(4) 0.0247(4) Uani 1 1 d . . . . .
N2 N 0.38704(14) 0.90737(19) 0.40188(5) 0.0312(4) Uani 1 1 d . . . . .
C1 C 0.35132(14) 0.6003(2) 0.25724(5) 0.0251(4) Uani 1 1 d . . . . .
H1 H 0.410285 0.629974 0.260603 0.030 Uiso 1 1 calc R U . . .
C2 C 0.28745(14) 0.6334(2) 0.28087(5) 0.0244(4) Uani 1 1 d . . . . .
C3 C 0.20126(15) 0.5892(2) 0.27502(6) 0.0288(4) Uani 1 1 d . . . . .
H3 H 0.155538 0.612135 0.290429 0.035 Uiso 1 1 calc R U . . .
C4 C 0.18262(15) 0.5116(2) 0.24665(6) 0.0322(5) Uani 1 1 d . . . . .
H4 H 0.124267 0.480202 0.242748 0.039 Uiso 1 1 calc R U . . .
C5 C 0.24901(15) 0.4802(2) 0.22415(5) 0.0287(4) Uani 1 1 d . . . . .
H5 H 0.236653 0.425961 0.204875 0.034 Uiso 1 1 calc R U . . .
C6 C 0.31271(14) 0.7069(2) 0.31207(5) 0.0255(4) Uani 1 1 d . . . . .
C7 C 0.38830(15) 0.6673(2) 0.32981(6) 0.0302(5) Uani 1 1 d . . . . .
H7 H 0.423326 0.594810 0.321531 0.036 Uiso 1 1 calc R U . . .
C8 C 0.41231(15) 0.7328(3) 0.35927(6) 0.0324(5) Uani 1 1 d . . . . .
H8 H 0.463227 0.704101 0.371312 0.039 Uiso 1 1 calc R U . . .
C9 C 0.36235(15) 0.8412(2) 0.37153(5) 0.0281(4) Uani 1 1 d . . . . .
C10 C 0.28718(15) 0.8806(2) 0.35382(6) 0.0296(4) Uani 1 1 d . . . . .
H10 H 0.252760 0.954136 0.361892 0.036 Uiso 1 1 calc R U . . .
C11 C 0.26211(15) 0.8137(2) 0.32456(5) 0.0286(4) Uani 1 1 d . . . . .
H11 H 0.210136 0.840590 0.312928 0.034 Uiso 1 1 calc R U . . .
C12 C 0.39148(15) 1.0508(2) 0.40295(5) 0.0277(4) Uani 1 1 d . . . . .
C13 C 0.42277(16) 1.1253(2) 0.37575(6) 0.0332(5) Uani 1 1 d . . . . .
H13 H 0.440291 1.080242 0.355589 0.040 Uiso 1 1 calc R U . . .
C14 C 0.42871(18) 1.2655(3) 0.37775(7) 0.0397(5) Uani 1 1 d . . . . .
H14 H 0.449522 1.315802 0.358873 0.048 Uiso 1 1 calc R U . . .
C15 C 0.4045(2) 1.3316(2) 0.40702(7) 0.0427(6) Uani 1 1 d . . . . .
H15 H 0.410145 1.427043 0.408623 0.051 Uiso 1 1 calc R U . . .
C16 C 0.37184(19) 1.2579(3) 0.43411(7) 0.0406(6) Uani 1 1 d . . . . .
H16 H 0.353812 1.303504 0.454126 0.049 Uiso 1 1 calc R U . . .
C17 C 0.36526(17) 1.1184(2) 0.43226(6) 0.0343(5) Uani 1 1 d . . . . .
H17 H 0.342864 1.068688 0.450963 0.041 Uiso 1 1 calc R U . . .
C18 C 0.42413(15) 0.8311(2) 0.42869(5) 0.0281(4) Uani 1 1 d . . . . .
C19 C 0.49935(16) 0.8751(2) 0.44563(6) 0.0320(5) Uani 1 1 d . . . . .
H19 H 0.526422 0.957970 0.439334 0.038 Uiso 1 1 calc R U . . .
C20 C 0.53496(17) 0.7985(3) 0.47162(7) 0.0385(5) Uani 1 1 d . . . . .
H20 H 0.586331 0.829357 0.483041 0.046 Uiso 1 1 calc R U . . .
C21 C 0.49628(18) 0.6772(2) 0.48113(7) 0.0391(5) Uani 1 1 d . . . . .
H21 H 0.520580 0.625135 0.499056 0.047 Uiso 1 1 calc R U . . .
C22 C 0.42196(18) 0.6332(2) 0.46418(6) 0.0372(5) Uani 1 1 d . . . . .
H22 H 0.395627 0.549612 0.470367 0.045 Uiso 1 1 calc R U . . .
C23 C 0.38533(16) 0.7088(2) 0.43837(6) 0.0330(5) Uani 1 1 d . . . . .
H23 H 0.333698 0.677735 0.427170 0.040 Uiso 1 1 calc R U . . .
C24 C 0.40573(15) 0.4989(2) 0.20530(5) 0.0291(4) Uani 1 1 d . . . . .
H24A H 0.421431 0.584063 0.193582 0.035 Uiso 1 1 calc R U . . .
H24B H 0.457984 0.469161 0.218369 0.035 Uiso 1 1 calc R U . . .
C25 C 0.38434(14) 0.3933(2) 0.17926(5) 0.0268(4) Uani 1 1 d . . . . .
C26 C 0.36156(15) 0.4296(2) 0.14636(6) 0.0284(4) Uani 1 1 d . . . . .
H26 H 0.358080 0.522508 0.140360 0.034 Uiso 1 1 calc R U . . .
C27 C 0.34390(14) 0.3311(2) 0.12224(5) 0.0268(4) Uani 1 1 d . . . . .
H27 H 0.327670 0.356500 0.099889 0.032 Uiso 1 1 calc R U . . .
C28 C 0.35006(14) 0.1950(2) 0.13093(5) 0.0264(4) Uani 1 1 d . . . . .
C29 C 0.37346(15) 0.1584(2) 0.16390(6) 0.0300(5) Uani 1 1 d . . . . .
H29 H 0.378183 0.065592 0.169805 0.036 Uiso 1 1 calc R U . . .
C30 C 0.38976(15) 0.2567(2) 0.18796(5) 0.0293(4) Uani 1 1 d . . . . .
H30 H 0.404675 0.231368 0.210442 0.035 Uiso 1 1 calc R U . . .
C31 C 0.33954(15) 0.0845(2) 0.10541(6) 0.0293(4) Uani 1 1 d . . . . .
C32 C 0.27861(14) 0.1014(2) 0.07605(5) 0.0269(4) Uani 1 1 d . . . . .
C33 C 0.20098(15) 0.1772(2) 0.07833(6) 0.0301(4) Uani 1 1 d . . . . .
H33 H 0.188159 0.226375 0.098395 0.036 Uiso 1 1 calc R U . . .
C34 C 0.14268(16) 0.1806(2) 0.05127(7) 0.0359(5) Uani 1 1 d . . . . .
H34 H 0.089197 0.230152 0.053042 0.043 Uiso 1 1 calc R U . . .
C35 C 0.16233(17) 0.1117(3) 0.02167(6) 0.0392(6) Uani 1 1 d . . . . .
H35 H 0.122985 0.115766 0.002974 0.047 Uiso 1 1 calc R U . . .
C36 C 0.23957(18) 0.0368(3) 0.01934(6) 0.0392(5) Uani 1 1 d . . . . .
H36 H 0.252923 -0.010243 -0.000991 0.047 Uiso 1 1 calc R U . . .
C37 C 0.29729(16) 0.0302(2) 0.04648(6) 0.0323(5) Uani 1 1 d . . . . .
H37 H 0.349457 -0.022660 0.044928 0.039 Uiso 1 1 calc R U . . .
O2 O 0.35467(14) 0.7952(2) 0.16671(6) 0.0511(5) Uani 1 1 d G . . . .
H2A H 0.367187 0.843013 0.148840 0.077 Uiso 1 1 d G U . . .
H2B H 0.400084 0.805483 0.179938 0.077 Uiso 1 1 d G 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 C31 1.223(3) . ?
N1 C1 1.352(3) . ?
N1 C5 1.346(3) . ?
N1 C24 1.502(3) . ?
N2 C9 1.416(3) . ?
N2 C12 1.420(3) . ?
N2 C18 1.416(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.384(3) . ?
C2 C3 1.397(3) . ?
C2 C6 1.481(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(3) . ?
C6 C11 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.398(3) . ?
C9 C10 1.393(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 C17 1.395(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(3) . ?
C18 C23 1.398(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.381(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(3) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.501(3) . ?
C25 C26 1.392(3) . ?
C25 C30 1.396(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.389(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.392(3) . ?
C28 C29 1.397(3) . ?
C28 C31 1.495(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.382(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.492(3) . ?
C32 C33 1.398(3) . ?
C32 C37 1.393(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.387(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.385(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.388(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.385(3) . ?
C37 H37 0.9500 . ?
O2 H2A 0.8702 . ?
O2 H2B 0.8701 . ?

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 C24 116.47(17) . . ?
C5 N1 C1 121.19(19) . . ?
C5 N1 C24 122.34(18) . . ?
C9 N2 C12 119.95(18) . . ?
C9 N2 C18 119.46(18) . . ?
C18 N2 C12 119.36(18) . . ?
N1 C1 H1 119.4 . . ?
N1 C1 C2 121.21(19) . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C3 117.94(19) . . ?
C1 C2 C6 119.75(19) . . ?
C3 C2 C6 122.22(19) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 120.0(2) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C2 119.38(19) . . ?
C11 C6 C2 121.58(19) . . ?
C11 C6 C7 119.03(19) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 N2 120.3(2) . . ?
C10 C9 N2 120.8(2) . . ?
C10 C9 C8 118.9(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C13 C12 N2 121.6(2) . . ?
C13 C12 C17 119.1(2) . . ?
C17 C12 N2 119.3(2) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.5(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 120.1(2) . . ?
C16 C17 H17 120.0 . . ?
C19 C18 N2 121.2(2) . . ?
C19 C18 C23 118.9(2) . . ?
C23 C18 N2 119.9(2) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.1(2) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 121.0(2) . . ?
C23 C22 H22 119.5 . . ?
C18 C23 H23 120.0 . . ?
C22 C23 C18 120.1(2) . . ?
C22 C23 H23 120.0 . . ?
N1 C24 H24A 108.9 . . ?
N1 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 N1 113.56(17) . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C26 C25 C24 120.9(2) . . ?
C26 C25 C30 119.61(19) . . ?
C30 C25 C24 119.45(19) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.5(2) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.7(2) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C29 119.8(2) . . ?
C27 C28 C31 122.2(2) . . ?
C29 C28 C31 117.80(19) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.3(2) . . ?
C30 C29 H29 119.8 . . ?
C25 C30 H30 120.0 . . ?
C29 C30 C25 120.1(2) . . ?
C29 C30 H30 120.0 . . ?
O1 C31 C28 119.9(2) . . ?
O1 C31 C32 119.6(2) . . ?
C32 C31 C28 120.53(19) . . ?
C33 C32 C31 122.1(2) . . ?
C37 C32 C31 118.0(2) . . ?
C37 C32 C33 119.7(2) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.0(2) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.1(2) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.0 . . ?
C34 C35 C36 120.0(2) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.4(2) . . ?
C37 C36 H36 119.8 . . ?
C32 C37 H37 120.1 . . ?
C36 C37 C32 119.8(2) . . ?
C36 C37 H37 120.1 . . ?
H2A O2 H2B 104.6 . . ?

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 C31 C32 C33 147.0(2) . . . . ?
O1 C31 C32 C37 -28.0(3) . . . . ?
N1 C1 C2 C3 -0.5(3) . . . . ?
N1 C1 C2 C6 176.16(19) . . . . ?
N1 C24 C25 C26 101.4(2) . . . . ?
N1 C24 C25 C30 -80.4(3) . . . . ?
N2 C9 C10 C11 -178.5(2) . . . . ?
N2 C12 C13 C14 -178.3(2) . . . . ?
N2 C12 C17 C16 177.9(2) . . . . ?
N2 C18 C19 C20 -179.5(2) . . . . ?
N2 C18 C23 C22 179.1(2) . . . . ?
C1 N1 C5 C4 2.1(3) . . . . ?
C1 N1 C24 C25 167.69(18) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
C1 C2 C6 C7 -43.9(3) . . . . ?
C1 C2 C6 C11 137.1(2) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C2 C6 C7 C8 -178.9(2) . . . . ?
C2 C6 C11 C10 179.9(2) . . . . ?
C3 C2 C6 C7 132.6(2) . . . . ?
C3 C2 C6 C11 -46.3(3) . . . . ?
C3 C4 C5 N1 -1.0(3) . . . . ?
C5 N1 C1 C2 -1.4(3) . . . . ?
C5 N1 C24 C25 -12.0(3) . . . . ?
C6 C2 C3 C4 -175.0(2) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C7 C6 C11 C10 1.0(3) . . . . ?
C7 C8 C9 N2 179.6(2) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 N2 C12 C13 -38.0(3) . . . . ?
C9 N2 C12 C17 143.1(2) . . . . ?
C9 N2 C18 C19 133.5(2) . . . . ?
C9 N2 C18 C23 -46.0(3) . . . . ?
C9 C10 C11 C6 -1.1(3) . . . . ?
C11 C6 C7 C8 0.1(3) . . . . ?
C12 N2 C9 C8 131.7(2) . . . . ?
C12 N2 C9 C10 -49.7(3) . . . . ?
C12 N2 C18 C19 -33.8(3) . . . . ?
C12 N2 C18 C23 146.7(2) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C13 C12 C17 C16 -0.9(4) . . . . ?
C13 C14 C15 C16 -1.8(4) . . . . ?
C14 C15 C16 C17 1.5(4) . . . . ?
C15 C16 C17 C12 -0.1(4) . . . . ?
C17 C12 C13 C14 0.6(4) . . . . ?
C18 N2 C9 C8 -35.6(3) . . . . ?
C18 N2 C9 C10 143.0(2) . . . . ?
C18 N2 C12 C13 129.2(2) . . . . ?
C18 N2 C12 C17 -49.6(3) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C18 C23 C22 -0.5(3) . . . . ?
C19 C20 C21 C22 0.4(4) . . . . ?
C20 C21 C22 C23 -0.8(4) . . . . ?
C21 C22 C23 C18 0.9(4) . . . . ?
C23 C18 C19 C20 0.0(3) . . . . ?
C24 N1 C1 C2 178.96(19) . . . . ?
C24 N1 C5 C4 -178.2(2) . . . . ?
C24 C25 C26 C27 178.5(2) . . . . ?
C24 C25 C30 C29 -177.6(2) . . . . ?
C25 C26 C27 C28 -0.8(3) . . . . ?
C26 C25 C30 C29 0.7(3) . . . . ?
C26 C27 C28 C29 0.4(3) . . . . ?
C26 C27 C28 C31 -174.6(2) . . . . ?
C27 C28 C29 C30 0.5(3) . . . . ?
C27 C28 C31 O1 147.7(2) . . . . ?
C27 C28 C31 C32 -32.8(3) . . . . ?
C28 C29 C30 C25 -1.1(3) . . . . ?
C28 C31 C32 C33 -32.5(3) . . . . ?
C28 C31 C32 C37 152.5(2) . . . . ?
C29 C28 C31 O1 -27.3(3) . . . . ?
C29 C28 C31 C32 152.2(2) . . . . ?
C30 C25 C26 C27 0.3(3) . . . . ?
C31 C28 C29 C30 175.7(2) . . . . ?
C31 C32 C33 C34 -174.5(2) . . . . ?
C31 C32 C37 C36 176.2(2) . . . . ?
C32 C33 C34 C35 -1.6(3) . . . . ?
C33 C32 C37 C36 1.1(3) . . . . ?
C33 C34 C35 C36 1.4(4) . . . . ?
C34 C35 C36 C37 0.1(4) . . . . ?
C35 C36 C37 C32 -1.3(4) . . . . ?
C37 C32 C33 C34 0.4(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 2.295
_oxdiff_exptl_absorpt_empirical_full_min 0.585
