# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

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

data_3bb_sq
_database_code_depnum_ccdc_archive 'CCDC 1936472'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan' 'Henan Normal University'
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-09-17 downloaded from the CCDC.
;
_audit_creation_date             2019-06-25
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C25 H26 N2 O2)'
_chemical_formula_sum            'C50 H52 N4 O4'
_chemical_formula_weight         772.95
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   12.8963(5)
_cell_length_b                   13.1501(3)
_cell_length_c                   17.1010(5)
_cell_angle_alpha                92.305(2)
_cell_angle_beta                 111.817(3)
_cell_angle_gamma                103.594(3)
_cell_volume                     2590.69(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10524
_cell_measurement_temperature    289(3)
_cell_measurement_theta_max      71.2460
_cell_measurement_theta_min      4.4270
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.991
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2
_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  0.0210
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24264
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.254
_diffrn_reflns_theta_min         3.493
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      289(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_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   -105.00  34.00   1.00    1.49    --  -35.37   0.00 -30.00  139
  2  ω   -105.00 -16.00   1.00    1.49    --  -35.37 -38.00 120.00   89
  3  ω    -52.00  32.00   1.00    1.49    --  -35.37  57.00  -1.00   84
  4  ω     23.00  89.00   1.00    1.49    --   35.37-125.00-120.00   66
  5  ω     23.00  89.00   1.00    1.49    --   35.37-125.00 150.00   66
  6  ω     23.00  89.00   1.00    1.49    --   35.37-125.00  90.00   66
  7  ω     23.00  89.00   1.00    1.49    --   35.37-125.00 -60.00   66
  8  ω     40.00 125.00   1.00    6.00    --  106.50 -61.00 120.00   85
  9  ω     88.00 173.00   1.00    6.00    --  106.50  61.00  30.00   85
 10  ω     37.00 176.00   1.00    6.00    --  106.50   0.00-150.00  139
 11  ω     37.00 109.00   1.00    6.00    --  106.50 -95.00  60.00   72
 12  ω     37.00 128.00   1.00    6.00    --  106.50 -30.00   0.00   91
 13  ω     37.00 112.00   1.00    6.00    --  106.50-111.00 150.00   75
 14  ω     37.00 112.00   1.00    6.00    --  106.50-111.00   0.00   75
 15  ω     88.00 173.00   1.00    6.00    --  106.50  61.00-150.00   85
 16  ω     80.00 174.00   1.00    6.00    --  106.50  77.00  60.00   94
 17  ω     37.00 112.00   1.00    6.00    --  106.50-111.00 -90.00   75
 18  ω     38.00 124.00   1.00    6.00    --  106.50 -45.00 -90.00   86
 19  ω     38.00 124.00   1.00    6.00    --  106.50 -45.00  90.00   86
 20  ω     40.00 125.00   1.00    6.00    --  106.50 -61.00-120.00   85
 21  ω     39.00 133.00   1.00    6.00    --  106.50 -77.00   0.00   94
 22  ω     37.00 109.00   1.00    6.00    --  106.50 -95.00-150.00   72
 23  ω   -103.00  -9.00   1.00    1.49    --  -35.37 -77.00 -90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1090452000
_diffrn_orient_matrix_UB_12      0.0143184000
_diffrn_orient_matrix_UB_13      -0.0201699000
_diffrn_orient_matrix_UB_21      0.0584763000
_diffrn_orient_matrix_UB_22      0.1029516000
_diffrn_orient_matrix_UB_23      0.0634786000
_diffrn_orient_matrix_UB_31      0.0504329000
_diffrn_orient_matrix_UB_32      -0.0633988000
_diffrn_orient_matrix_UB_33      0.0719146000
_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                8040
_reflns_number_total             9887
_reflns_odcompleteness_completeness 99.90
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         9887
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      1.070
_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)+(0.0824P)²+0.3952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1603
_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 C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C42, C43
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
3.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13), C21(H21), C37(H37), C38(H38), C46(H46)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C39(H39A,H39B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C16(H16), C17(H17),
 C19(H19), C20(H20), C26(H26), C27(H27), C30(H30), C31(H31), C32(H32), C33(H33),
  C35(H35), C41(H41), C42(H42), C44(H44), C45(H45)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C47(H47A,H47B,
 H47C), C48(H48A,H48C,H48B), C50(H50A,H50B,H50C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O3(H3)
;
_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
C1 C 0.27001(18) 0.90999(14) 0.39355(11) 0.0546(4) Uani 1 1 d . . . . .
H1 H 0.3201 0.9763 0.4192 0.066 Uiso 1 1 calc R . . . .
N1 N 0.24640(11) 0.82415(10) 0.43293(8) 0.0414(3) Uani 1 1 d . . . . .
O1 O 0.50668(11) 0.70058(11) 0.65637(9) 0.0640(4) Uani 1 1 d . . . . .
H1A H 0.5705 0.7257 0.6949 0.096 Uiso 1 1 calc GR . . . .
C2 C 0.2055(2) 0.87853(16) 0.30969(12) 0.0661(5) Uani 1 1 d . . . . .
H2 H 0.2037 0.9212 0.2674 0.079 Uiso 1 1 calc R . . . .
N2 N 0.14358(15) 0.77566(12) 0.29579(9) 0.0575(4) Uani 1 1 d . . . . .
O2 O 0.51299(13) 0.87000(12) 0.64703(11) 0.0793(5) Uani 1 1 d . . . . .
C3 C 0.16986(14) 0.74363(13) 0.37196(9) 0.0441(3) Uani 1 1 d . . . . .
C4 C 0.12376(15) 0.63597(13) 0.38571(10) 0.0460(3) Uani 1 1 d . . . . .
C5 C 0.01709(18) 0.57685(17) 0.32531(12) 0.0651(5) Uani 1 1 d . . . . .
H5 H -0.0239 0.6081 0.2804 0.078 Uiso 1 1 calc R . . . .
C6 C -0.0292(2) 0.47231(19) 0.33082(16) 0.0834(7) Uani 1 1 d . . . . .
H6 H -0.1011 0.4344 0.2904 0.100 Uiso 1 1 calc R . . . .
C7 C 0.0320(2) 0.42458(18) 0.39665(16) 0.0806(7) Uani 1 1 d . . . . .
H7 H 0.0015 0.3543 0.4004 0.097 Uiso 1 1 calc R . . . .
C8 C 0.13777(19) 0.48107(15) 0.45639(13) 0.0635(5) Uani 1 1 d . . . . .
H8 H 0.1788 0.4478 0.4998 0.076 Uiso 1 1 calc R . . . .
C9 C 0.18585(15) 0.58807(13) 0.45368(10) 0.0460(3) Uani 1 1 d . . . . .
C10 C 0.29883(14) 0.63893(13) 0.52127(10) 0.0457(3) Uani 1 1 d . . . . .
H10 H 0.3441 0.5939 0.5454 0.055 Uiso 1 1 calc R . . . .
C11 C 0.34607(13) 0.74108(13) 0.55323(9) 0.0422(3) Uani 1 1 d . . . . .
C12 C 0.28461(13) 0.82585(12) 0.52560(9) 0.0401(3) Uani 1 1 d . . . . .
H12 H 0.3405 0.8944 0.5530 0.048 Uiso 1 1 calc R . . . .
C13 C 0.18300(14) 0.81509(13) 0.55401(10) 0.0438(3) Uani 1 1 d . . . . .
H13 H 0.1276 0.7462 0.5274 0.053 Uiso 1 1 calc R . . . .
C14 C 0.11933(16) 0.90094(15) 0.52502(13) 0.0558(4) Uani 1 1 d . . . . .
H14A H 0.1617 0.9658 0.5644 0.067 Uiso 1 1 calc R . . . .
H14B H 0.1174 0.9149 0.4693 0.067 Uiso 1 1 calc R . . . .
C15 C -0.00236(16) 0.86846(14) 0.52089(12) 0.0507(4) Uani 1 1 d . . . . .
C16 C -0.03152(17) 0.89235(16) 0.58806(12) 0.0565(4) Uani 1 1 d . . . . .
H16 H 0.0261 0.9322 0.6380 0.068 Uiso 1 1 calc R . . . .
C17 C -0.14386(17) 0.85868(16) 0.58322(12) 0.0557(4) Uani 1 1 d . . . . .
H17 H -0.1599 0.8754 0.6301 0.067 Uiso 1 1 calc R . . . .
C18 C -0.23228(17) 0.80100(16) 0.51061(13) 0.0577(4) Uani 1 1 d . . . . .
C19 C -0.20450(19) 0.77736(19) 0.44230(14) 0.0709(6) Uani 1 1 d . . . . .
H19 H -0.2628 0.7390 0.3920 0.085 Uiso 1 1 calc R . . . .
C20 C -0.09124(18) 0.80995(18) 0.44759(13) 0.0655(5) Uani 1 1 d . . . . .
H20 H -0.0748 0.7922 0.4011 0.079 Uiso 1 1 calc R . . . .
C21 C -0.35598(18) 0.76395(19) 0.50516(15) 0.0690(5) Uani 1 1 d . . . . .
H21 H -0.3561 0.7912 0.5593 0.083 Uiso 1 1 calc R . . . .
C22 C -0.4386(2) 0.8082(2) 0.43546(19) 0.0900(8) Uani 1 1 d . . . . .
H22A H -0.4441 0.7796 0.3811 0.135 Uiso 1 1 calc GR . . . .
H22B H -0.4102 0.8837 0.4434 0.135 Uiso 1 1 calc GR . . . .
H22C H -0.5139 0.7892 0.4378 0.135 Uiso 1 1 calc GR . . . .
C23 C -0.3982(2) 0.6437(2) 0.49426(18) 0.0834(7) Uani 1 1 d . . . . .
H23A H -0.4022 0.6144 0.4405 0.125 Uiso 1 1 calc GR . . . .
H23B H -0.4738 0.6234 0.4960 0.125 Uiso 1 1 calc GR . . . .
H23C H -0.3452 0.6175 0.5394 0.125 Uiso 1 1 calc GR . . . .
C24 C 0.46363(14) 0.77651(15) 0.62397(10) 0.0501(4) Uani 1 1 d . . . . .
C25 C 0.22636(19) 0.8173(2) 0.65017(12) 0.0694(6) Uani 1 1 d . . . . .
H25A H 0.2844 0.8825 0.6777 0.104 Uiso 1 1 calc GR . . . .
H25B H 0.2592 0.7591 0.6658 0.104 Uiso 1 1 calc GR . . . .
H25C H 0.1627 0.8116 0.6676 0.104 Uiso 1 1 calc GR . . . .
N3 N 0.88537(12) 0.80524(11) 0.87380(8) 0.0451(3) Uani 1 1 d . . . . .
O3 O 1.01019(13) 0.69919(11) 1.13602(7) 0.0622(3) Uani 1 1 d . . . . .
H3 H 1.0531 0.7233 1.1856 0.093 Uiso 1 1 calc GR . . . .
N4 N 0.71050(13) 0.77391(13) 0.77425(10) 0.0584(4) Uani 1 1 d . . . . .
O4 O 1.12942(13) 0.83255(13) 1.10880(8) 0.0710(4) Uani 1 1 d . . . . .
C26 C 0.86282(17) 0.90137(15) 0.86138(12) 0.0557(4) Uani 1 1 d . . . . .
H26 H 0.9116 0.9674 0.8893 0.067 Uiso 1 1 calc R . . . .
C27 C 0.75434(17) 0.88008(16) 0.79976(14) 0.0641(5) Uani 1 1 d . . . . .
H27 H 0.7156 0.9306 0.7781 0.077 Uiso 1 1 calc R . . . .
C28 C 0.79167(14) 0.72963(14) 0.82042(10) 0.0466(4) Uani 1 1 d . . . . .
C29 C 0.78090(14) 0.61608(14) 0.81208(10) 0.0476(4) Uani 1 1 d . . . . .
C30 C 0.71270(18) 0.55585(17) 0.73269(12) 0.0630(5) Uani 1 1 d . . . . .
H30 H 0.6774 0.5889 0.6869 0.076 Uiso 1 1 calc R . . . .
C31 C 0.6966(2) 0.44802(18) 0.72081(14) 0.0728(6) Uani 1 1 d . . . . .
H31 H 0.6526 0.4093 0.6671 0.087 Uiso 1 1 calc R . . . .
C32 C 0.7462(2) 0.39735(17) 0.78898(15) 0.0719(6) Uani 1 1 d . . . . .
H32 H 0.7356 0.3247 0.7812 0.086 Uiso 1 1 calc R . . . .
C33 C 0.81125(17) 0.45557(15) 0.86841(13) 0.0600(5) Uani 1 1 d . . . . .
H33 H 0.8421 0.4209 0.9144 0.072 Uiso 1 1 calc R . . . .
C34 C 0.83190(14) 0.56533(14) 0.88153(10) 0.0472(4) Uani 1 1 d . . . . .
C35 C 0.90431(15) 0.61963(14) 0.96811(10) 0.0478(4) Uani 1 1 d . . . . .
H35 H 0.8998 0.5813 1.0118 0.057 Uiso 1 1 calc R . . . .
C36 C 0.97565(13) 0.71669(13) 0.99222(9) 0.0429(3) Uani 1 1 d . . . . .
C37 C 0.99681(13) 0.78951(13) 0.93017(9) 0.0436(3) Uani 1 1 d . . . . .
H37 H 1.0465 0.8582 0.9630 0.052 Uiso 1 1 calc R . . . .
C38 C 1.05959(15) 0.74849(16) 0.87915(10) 0.0529(4) Uani 1 1 d . . . . .
H38 H 1.0221 0.6730 0.8594 0.063 Uiso 1 1 calc R . . . .
C39 C 1.18553(16) 0.76065(19) 0.93951(12) 0.0645(5) Uani 1 1 d . . . . .
H39A H 1.2273 0.8350 0.9517 0.077 Uiso 1 1 calc R . . . .
H39B H 1.1863 0.7373 0.9928 0.077 Uiso 1 1 calc R . . . .
C40 C 1.24844(17) 0.69956(18) 0.90507(12) 0.0620(5) Uani 1 1 d . . . . .
C41 C 1.2278(3) 0.5924(2) 0.90389(18) 0.0896(8) Uani 1 1 d . . . . .
H41 H 1.1723 0.5563 0.9227 0.107 Uiso 1 1 calc R . . . .
C42 C 1.2897(3) 0.5362(3) 0.8746(2) 0.1012(9) Uani 1 1 d . U . . .
H42 H 1.2747 0.4634 0.8740 0.121 Uiso 1 1 calc R . . . .
C43 C 1.3732(2) 0.5887(3) 0.84648(15) 0.0866(8) Uani 1 1 d . U . . .
C44 C 1.3881(2) 0.6934(3) 0.84491(18) 0.0899(8) Uani 1 1 d . . . . .
H44 H 1.4406 0.7296 0.8236 0.108 Uiso 1 1 calc R . . . .
C45 C 1.3285(2) 0.7480(2) 0.87365(16) 0.0800(6) Uani 1 1 d . . . . .
H45 H 1.3425 0.8204 0.8720 0.096 Uiso 1 1 calc R . . . .
C46 C 1.4431(4) 0.5290(4) 0.8160(2) 0.1262(14) Uani 1 1 d . . . . .
H46 H 1.4947 0.5856 0.8016 0.151 Uiso 1 1 calc R . . . .
C47 C 1.5241(4) 0.4896(4) 0.8838(3) 0.1423(16) Uani 1 1 d . . . . .
H47A H 1.5659 0.5442 0.9318 0.213 Uiso 1 1 calc GR . . . .
H47B H 1.5777 0.4687 0.8642 0.213 Uiso 1 1 calc GR . . . .
H47C H 1.4822 0.4298 0.9004 0.213 Uiso 1 1 calc GR . . . .
C48 C 1.3747(4) 0.4630(4) 0.7351(3) 0.1594(19) Uani 1 1 d . . . . .
H48A H 1.3239 0.4017 0.7429 0.239 Uiso 1 1 calc GR . . . .
H48C H 1.4251 0.4414 0.7123 0.239 Uiso 1 1 calc GR . . . .
H48B H 1.3295 0.5020 0.6964 0.239 Uiso 1 1 calc GR . . . .
C49 C 1.04565(15) 0.75636(14) 1.08503(10) 0.0475(4) Uani 1 1 d . . . . .
C50 C 1.0524(2) 0.8036(2) 0.80171(14) 0.0816(7) Uani 1 1 d . . . . .
H50A H 0.9726 0.7903 0.7636 0.122 Uiso 1 1 calc GR . . . .
H50B H 1.0943 0.7770 0.7733 0.122 Uiso 1 1 calc GR . . . .
H50C H 1.0856 0.8783 0.8193 0.122 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 N1 1.368(2) . ?
C1 C2 1.350(3) . ?
N1 C3 1.356(2) . ?
N1 C12 1.4719(18) . ?
O1 H1A 0.8200 . ?
O1 C24 1.299(2) . ?
C2 H2 0.9300 . ?
C2 N2 1.360(3) . ?
N2 C3 1.331(2) . ?
O2 C24 1.216(2) . ?
C3 C4 1.466(2) . ?
C4 C5 1.393(2) . ?
C4 C9 1.412(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.372(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.408(3) . ?
C9 C10 1.461(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.335(2) . ?
C11 C12 1.508(2) . ?
C11 C24 1.496(2) . ?
C12 H12 0.9800 . ?
C12 C13 1.538(2) . ?
C13 H13 0.9800 . ?
C13 C14 1.540(2) . ?
C13 C25 1.524(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.500(3) . ?
C15 C16 1.381(3) . ?
C15 C20 1.385(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(3) . ?
C18 C19 1.387(3) . ?
C18 C21 1.520(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9800 . ?
C21 C22 1.516(3) . ?
C21 C23 1.526(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N3 C26 1.370(2) . ?
N3 C28 1.351(2) . ?
N3 C37 1.4709(19) . ?
O3 H3 0.8200 . ?
O3 C49 1.312(2) . ?
N4 C27 1.362(3) . ?
N4 C28 1.329(2) . ?
O4 C49 1.212(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.357(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.463(2) . ?
C29 C30 1.394(2) . ?
C29 C34 1.407(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.379(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.386(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.379(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.398(3) . ?
C34 C35 1.466(2) . ?
C35 H35 0.9300 . ?
C35 C36 1.330(2) . ?
C36 C37 1.514(2) . ?
C36 C49 1.501(2) . ?
C37 H37 0.9800 . ?
C37 C38 1.549(2) . ?
C38 H38 0.9800 . ?
C38 C39 1.532(2) . ?
C38 C50 1.518(3) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.508(3) . ?
C40 C41 1.370(4) . ?
C40 C45 1.375(3) . ?
C41 H41 0.9300 . ?
C41 C42 1.407(4) . ?
C42 H42 0.9300 . ?
C42 C43 1.388(4) . ?
C43 C44 1.348(4) . ?
C43 C46 1.533(4) . ?
C44 H44 0.9300 . ?
C44 C45 1.363(4) . ?
C45 H45 0.9300 . ?
C46 H46 0.9800 . ?
C46 C47 1.452(5) . ?
C46 C48 1.442(5) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 H48A 0.9600 . ?
C48 H48C 0.9600 . ?
C48 H48B 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?

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 C1 H1 127.1 . . ?
C2 C1 H1 127.1 . . ?
C2 C1 N1 105.83(16) . . ?
C1 N1 C12 124.88(14) . . ?
C3 N1 C1 107.78(13) . . ?
C3 N1 C12 126.75(13) . . ?
C24 O1 H1A 109.5 . . ?
C1 C2 H2 124.8 . . ?
C1 C2 N2 110.45(16) . . ?
N2 C2 H2 124.8 . . ?
C3 N2 C2 106.08(15) . . ?
N1 C3 C4 126.11(14) . . ?
N2 C3 N1 109.86(15) . . ?
N2 C3 C4 124.01(15) . . ?
C5 C4 C3 117.72(15) . . ?
C5 C4 C9 119.16(16) . . ?
C9 C4 C3 122.98(15) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.32(19) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.9(2) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.1 . . ?
C7 C8 C9 121.72(19) . . ?
C9 C8 H8 119.1 . . ?
C4 C9 C10 125.70(15) . . ?
C8 C9 C4 118.14(16) . . ?
C8 C9 C10 116.13(15) . . ?
C9 C10 H10 115.5 . . ?
C11 C10 C9 128.98(15) . . ?
C11 C10 H10 115.5 . . ?
C10 C11 C12 123.66(14) . . ?
C10 C11 C24 120.30(15) . . ?
C24 C11 C12 115.95(14) . . ?
N1 C12 C11 109.94(12) . . ?
N1 C12 H12 107.8 . . ?
N1 C12 C13 111.67(12) . . ?
C11 C12 H12 107.8 . . ?
C11 C12 C13 111.69(13) . . ?
C13 C12 H12 107.8 . . ?
C12 C13 H13 107.9 . . ?
C12 C13 C14 111.75(13) . . ?
C14 C13 H13 107.9 . . ?
C25 C13 C12 109.91(14) . . ?
C25 C13 H13 107.9 . . ?
C25 C13 C14 111.34(15) . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 C13 111.83(14) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C16 C15 C14 123.18(18) . . ?
C16 C15 C20 117.01(18) . . ?
C20 C15 C14 119.80(17) . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C17 121.86(18) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.32(18) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 117.46(18) . . ?
C17 C18 C21 121.39(18) . . ?
C19 C18 C21 121.15(19) . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.21(19) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 C19 121.13(18) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C18 C21 H21 107.3 . . ?
C18 C21 C23 111.81(19) . . ?
C22 C21 C18 111.9(2) . . ?
C22 C21 H21 107.3 . . ?
C22 C21 C23 110.9(2) . . ?
C23 C21 H21 107.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 C24 C11 114.89(16) . . ?
O2 C24 O1 124.30(16) . . ?
O2 C24 C11 120.80(15) . . ?
C13 C25 H25A 109.5 . . ?
C13 C25 H25B 109.5 . . ?
C13 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 N3 C37 125.10(14) . . ?
C28 N3 C26 108.16(14) . . ?
C28 N3 C37 126.53(14) . . ?
C49 O3 H3 109.5 . . ?
C28 N4 C27 106.44(15) . . ?
N3 C26 H26 127.2 . . ?
C27 C26 N3 105.60(17) . . ?
C27 C26 H26 127.2 . . ?
N4 C27 H27 125.0 . . ?
C26 C27 N4 110.02(16) . . ?
C26 C27 H27 125.0 . . ?
N3 C28 C29 125.74(14) . . ?
N4 C28 N3 109.78(15) . . ?
N4 C28 C29 124.45(15) . . ?
C30 C29 C28 118.13(16) . . ?
C30 C29 C34 119.20(17) . . ?
C34 C29 C28 122.60(15) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 C29 121.16(19) . . ?
C31 C30 H30 119.4 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 119.98(19) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.3 . . ?
C33 C32 C31 119.5(2) . . ?
C33 C32 H32 120.3 . . ?
C32 C33 H33 119.2 . . ?
C32 C33 C34 121.61(19) . . ?
C34 C33 H33 119.2 . . ?
C29 C34 C35 124.37(15) . . ?
C33 C34 C29 118.51(16) . . ?
C33 C34 C35 117.11(15) . . ?
C34 C35 H35 115.8 . . ?
C36 C35 C34 128.34(15) . . ?
C36 C35 H35 115.8 . . ?
C35 C36 C37 123.33(14) . . ?
C35 C36 C49 119.92(15) . . ?
C49 C36 C37 116.64(14) . . ?
N3 C37 C36 108.75(13) . . ?
N3 C37 H37 107.8 . . ?
N3 C37 C38 111.78(12) . . ?
C36 C37 H37 107.8 . . ?
C36 C37 C38 112.59(14) . . ?
C38 C37 H37 107.8 . . ?
C37 C38 H38 108.0 . . ?
C39 C38 C37 108.36(14) . . ?
C39 C38 H38 108.0 . . ?
C50 C38 C37 112.61(17) . . ?
C50 C38 H38 108.0 . . ?
C50 C38 C39 111.75(18) . . ?
C38 C39 H39A 108.8 . . ?
C38 C39 H39B 108.8 . . ?
H39A C39 H39B 107.7 . . ?
C40 C39 C38 113.98(16) . . ?
C40 C39 H39A 108.8 . . ?
C40 C39 H39B 108.8 . . ?
C41 C40 C39 120.9(2) . . ?
C41 C40 C45 117.0(2) . . ?
C45 C40 C39 122.1(2) . . ?
C40 C41 H41 119.6 . . ?
C40 C41 C42 120.7(3) . . ?
C42 C41 H41 119.6 . . ?
C41 C42 H42 119.8 . . ?
C43 C42 C41 120.4(3) . . ?
C43 C42 H42 119.8 . . ?
C42 C43 C46 121.1(3) . . ?
C44 C43 C42 117.5(3) . . ?
C44 C43 C46 121.4(3) . . ?
C43 C44 H44 119.0 . . ?
C43 C44 C45 122.0(3) . . ?
C45 C44 H44 119.0 . . ?
C40 C45 H45 118.9 . . ?
C44 C45 C40 122.2(3) . . ?
C44 C45 H45 118.9 . . ?
C43 C46 H46 102.6 . . ?
C47 C46 C43 113.4(3) . . ?
C47 C46 H46 102.6 . . ?
C48 C46 C43 112.8(3) . . ?
C48 C46 H46 102.6 . . ?
C48 C46 C47 119.8(4) . . ?
C46 C47 H47A 109.5 . . ?
C46 C47 H47B 109.5 . . ?
C46 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C46 C48 H48A 109.5 . . ?
C46 C48 H48C 109.5 . . ?
C46 C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48C C48 H48B 109.5 . . ?
O3 C49 C36 114.01(15) . . ?
O4 C49 O3 124.38(15) . . ?
O4 C49 C36 121.56(15) . . ?
C38 C50 H50A 109.5 . . ?
C38 C50 H50B 109.5 . . ?
C38 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 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
C1 N1 C3 N2 -0.5(2) . . . . ?
C1 N1 C3 C4 178.03(17) . . . . ?
C1 N1 C12 C11 -127.57(17) . . . . ?
C1 N1 C12 C13 107.88(18) . . . . ?
C1 C2 N2 C3 0.3(3) . . . . ?
N1 C1 C2 N2 -0.6(3) . . . . ?
N1 C3 C4 C5 155.54(18) . . . . ?
N1 C3 C4 C9 -28.8(3) . . . . ?
N1 C12 C13 C14 -55.85(18) . . . . ?
N1 C12 C13 C25 -179.98(15) . . . . ?
C2 C1 N1 C3 0.7(2) . . . . ?
C2 C1 N1 C12 -171.02(17) . . . . ?
C2 N2 C3 N1 0.2(2) . . . . ?
C2 N2 C3 C4 -178.42(18) . . . . ?
N2 C3 C4 C5 -26.1(3) . . . . ?
N2 C3 C4 C9 149.54(18) . . . . ?
C3 N1 C12 C11 62.34(19) . . . . ?
C3 N1 C12 C13 -62.2(2) . . . . ?
C3 C4 C5 C6 176.0(2) . . . . ?
C3 C4 C9 C8 -174.31(17) . . . . ?
C3 C4 C9 C10 3.7(3) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C4 C9 C10 C11 27.8(3) . . . . ?
C5 C4 C9 C8 1.3(3) . . . . ?
C5 C4 C9 C10 179.31(18) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C7 C8 C9 C4 -2.0(3) . . . . ?
C7 C8 C9 C10 179.8(2) . . . . ?
C8 C9 C10 C11 -154.09(19) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
C9 C10 C11 C12 2.8(3) . . . . ?
C9 C10 C11 C24 179.16(16) . . . . ?
C10 C11 C12 N1 -55.8(2) . . . . ?
C10 C11 C12 C13 68.72(19) . . . . ?
C10 C11 C24 O1 -7.6(2) . . . . ?
C10 C11 C24 O2 171.62(18) . . . . ?
C11 C12 C13 C14 -179.41(14) . . . . ?
C11 C12 C13 C25 56.46(19) . . . . ?
C12 N1 C3 N2 170.95(15) . . . . ?
C12 N1 C3 C4 -10.5(3) . . . . ?
C12 C11 C24 O1 168.97(15) . . . . ?
C12 C11 C24 O2 -11.8(2) . . . . ?
C12 C13 C14 C15 157.52(15) . . . . ?
C13 C14 C15 C16 92.0(2) . . . . ?
C13 C14 C15 C20 -86.8(2) . . . . ?
C14 C15 C16 C17 -178.06(17) . . . . ?
C14 C15 C20 C19 179.0(2) . . . . ?
C15 C16 C17 C18 -1.0(3) . . . . ?
C16 C15 C20 C19 0.2(3) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C16 C17 C18 C21 -179.96(19) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C17 C18 C21 C22 119.5(2) . . . . ?
C17 C18 C21 C23 -115.4(2) . . . . ?
C18 C19 C20 C15 -0.9(4) . . . . ?
C19 C18 C21 C22 -60.7(3) . . . . ?
C19 C18 C21 C23 64.4(3) . . . . ?
C20 C15 C16 C17 0.7(3) . . . . ?
C21 C18 C19 C20 -179.1(2) . . . . ?
C24 C11 C12 N1 127.72(14) . . . . ?
C24 C11 C12 C13 -107.75(15) . . . . ?
C25 C13 C14 C15 -79.1(2) . . . . ?
N3 C26 C27 N4 -0.2(2) . . . . ?
N3 C28 C29 C30 -148.52(18) . . . . ?
N3 C28 C29 C34 34.5(3) . . . . ?
N3 C37 C38 C39 165.96(15) . . . . ?
N3 C37 C38 C50 41.8(2) . . . . ?
N4 C28 C29 C30 29.6(3) . . . . ?
N4 C28 C29 C34 -147.31(18) . . . . ?
C26 N3 C28 N4 0.2(2) . . . . ?
C26 N3 C28 C29 178.62(17) . . . . ?
C26 N3 C37 C36 125.23(17) . . . . ?
C26 N3 C37 C38 -109.85(19) . . . . ?
C27 N4 C28 N3 -0.3(2) . . . . ?
C27 N4 C28 C29 -178.74(18) . . . . ?
C28 N3 C26 C27 0.0(2) . . . . ?
C28 N3 C37 C36 -60.8(2) . . . . ?
C28 N3 C37 C38 64.2(2) . . . . ?
C28 N4 C27 C26 0.3(2) . . . . ?
C28 C29 C30 C31 -178.5(2) . . . . ?
C28 C29 C34 C33 176.29(17) . . . . ?
C28 C29 C34 C35 -2.5(3) . . . . ?
C29 C30 C31 C32 1.7(4) . . . . ?
C29 C34 C35 C36 -32.5(3) . . . . ?
C30 C29 C34 C33 -0.6(3) . . . . ?
C30 C29 C34 C35 -179.40(18) . . . . ?
C30 C31 C32 C33 0.1(4) . . . . ?
C31 C32 C33 C34 -2.2(3) . . . . ?
C32 C33 C34 C29 2.4(3) . . . . ?
C32 C33 C34 C35 -178.70(19) . . . . ?
C33 C34 C35 C36 148.73(19) . . . . ?
C34 C29 C30 C31 -1.5(3) . . . . ?
C34 C35 C36 C37 -1.8(3) . . . . ?
C34 C35 C36 C49 -177.90(16) . . . . ?
C35 C36 C37 N3 58.1(2) . . . . ?
C35 C36 C37 C38 -66.4(2) . . . . ?
C35 C36 C49 O3 -14.9(2) . . . . ?
C35 C36 C49 O4 162.76(18) . . . . ?
C36 C37 C38 C39 -71.28(19) . . . . ?
C36 C37 C38 C50 164.58(17) . . . . ?
C37 N3 C26 C27 174.90(16) . . . . ?
C37 N3 C28 N4 -174.60(15) . . . . ?
C37 N3 C28 C29 3.8(3) . . . . ?
C37 C36 C49 O3 168.75(15) . . . . ?
C37 C36 C49 O4 -13.6(2) . . . . ?
C37 C38 C39 C40 165.35(17) . . . . ?
C38 C39 C40 C41 -76.1(3) . . . . ?
C38 C39 C40 C45 103.9(2) . . . . ?
C39 C40 C41 C42 -177.7(2) . . . . ?
C39 C40 C45 C44 177.9(2) . . . . ?
C40 C41 C42 C43 0.2(5) . . . . ?
C41 C40 C45 C44 -2.0(4) . . . . ?
C41 C42 C43 C44 -3.0(4) . . . . ?
C41 C42 C43 C46 178.8(3) . . . . ?
C42 C43 C44 C45 3.3(4) . . . . ?
C42 C43 C46 C47 -69.1(5) . . . . ?
C42 C43 C46 C48 71.3(5) . . . . ?
C43 C44 C45 C40 -0.8(4) . . . . ?
C44 C43 C46 C47 112.7(4) . . . . ?
C44 C43 C46 C48 -106.9(5) . . . . ?
C45 C40 C41 C42 2.3(4) . . . . ?
C46 C43 C44 C45 -178.4(3) . . . . ?
C49 C36 C37 N3 -125.71(15) . . . . ?
C49 C36 C37 C38 109.85(16) . . . . ?
C50 C38 C39 C40 -70.0(3) . . . . ?

loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 0 1 2.812

_platon_squeeze_details          
;
TITL 3bb_a.res in P-1
CELL   12.8963   13.1501   17.1010     92.31    111.82    103.59
SPGR P-1
# Solvent Accessible Volume =       608
# Electrons Found in S.A.V. =       174
# Note: Atoms in Void as Cxxx and Qxxx all others
C101 0.799 0.908 0.073 !      10.61 eA-3
C102 0.482 0.900 0.126 !       5.38 eA-3
C103 0.901 0.922 0.058 !       4.17 eA-3
C104 0.841 0.854 0.190 !       2.77 eA-3
C105 0.702 0.784 0.014 !       2.71 eA-3
C106 0.438 0.887 0.223 !       2.01 eA-3
C107 0.602 0.977 0.138 !       1.94 eA-3
C108 0.411 1.005 0.094 !       1.51 eA-3
C109 0.620 0.892 0.220 !       1.08 eA-3
Q110 0.606 0.535 0.177 !       0.57 eA-3
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 1.000 602 174 ' '

_platon_squeeze_void_probe_radius 1.20

_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 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.649
####################################################################### 
# 
# 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_3k
_database_code_depnum_ccdc_archive 'CCDC 1936552'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan' 'Henan Normal University'
_audit_update_record             
;
2019-06-26 deposited with the CCDC.	2019-09-17 downloaded from the CCDC.
;
_audit_creation_date             2019-06-26
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 F N2 O2'
_chemical_formula_sum            'C21 H17 F N2 O2'
_chemical_formula_weight         348.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 F1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.7924(3)
_cell_length_b                   10.9272(3)
_cell_length_c                   18.0980(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1738.79(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2247
_cell_measurement_temperature    296.93(13)
_cell_measurement_theta_max      72.3240
_cell_measurement_theta_min      4.7240
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5171
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.436
_diffrn_reflns_theta_min         4.727
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.93(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  29.00   1.00    1.65    --  -40.77  44.00 -84.00   93
  2  ω    109.00 134.00   1.00    6.59    --  103.55  78.00  69.00   25
  3  ω    151.00 177.00   1.00    6.59    --  103.55  78.00  69.00   26
  4  ω     99.00 129.00   1.00    6.59    --  103.55 -44.00 124.00   30
  5  ω     98.00 161.00   1.00    6.59    --  103.55 122.00 141.00   63
  6  ω   -101.00 -61.00   1.00    1.65    --  -40.77-152.00-100.00   40
  7  ω     -6.00  43.00   1.00    1.65    --   40.77 -38.00  30.00   49
  8  ω    108.00 170.00   1.00    6.59    --  103.55 111.00 -60.00   62
  9  ω    136.00 168.00   1.00    6.59    --  103.55 111.00-180.00   32
 10  ω    101.00 177.00   1.00    6.59    --  103.55 111.00-120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0896337000
_diffrn_orient_matrix_UB_12      -0.0254211000
_diffrn_orient_matrix_UB_13      0.0714996000
_diffrn_orient_matrix_UB_21      -0.0309742000
_diffrn_orient_matrix_UB_22      0.1379152000
_diffrn_orient_matrix_UB_23      0.0087029000
_diffrn_orient_matrix_UB_31      -0.1473827000
_diffrn_orient_matrix_UB_32      -0.0135960000
_diffrn_orient_matrix_UB_33      -0.0454274000
_diffrn_oxdiff_digest_frames     
;
01b4e1b6d4c14fd69fbb056d835ee32406000309db0
;
_diffrn_oxdiff_digest_hkl        
;
012c32694eb0a1370e9c18db8116761dc2068a
;
_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         0.576
_reflns_Friedel_fraction_full    0.813
_reflns_Friedel_fraction_max     0.762
_reflns_number_gt                2671
_reflns_number_total             3045
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 924 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.019
_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)+(0.0431P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0822
_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) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13B,H13A), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C5(H5), C6(H6), C7(H7), C10(H10), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
C1 C 0.1372(3) 0.4359(2) 0.76641(14) 0.0402(5) Uani 1 1 d . . . . .
H1 H 0.1809 0.3701 0.7911 0.048 Uiso 1 1 calc R . . . .
F1 F 0.41066(18) 0.89722(15) 0.56424(10) 0.0575(4) Uani 1 1 d . . . . .
N1 N 0.20448(19) 0.50809(16) 0.71356(10) 0.0321(4) Uani 1 1 d . . . . .
O1 O 0.63102(19) 0.49146(18) 0.76217(11) 0.0528(5) Uani 1 1 d . . . . .
C2 C -0.0055(3) 0.4802(2) 0.77526(15) 0.0451(6) Uani 1 1 d . . . . .
H2A H -0.0780 0.4487 0.8075 0.054 Uiso 1 1 calc R . . . .
N2 N -0.0267(2) 0.57814(19) 0.72949(12) 0.0389(5) Uani 1 1 d . . . . .
O2 O 0.70605(19) 0.66658(16) 0.71065(13) 0.0523(5) Uani 1 1 d . . . . .
H2 H 0.7914 0.6417 0.7211 0.078 Uiso 1 1 calc GR . . . .
C3 C 0.1031(2) 0.5944(2) 0.69238(12) 0.0317(4) Uani 1 1 d . . . . .
C4 C 0.1280(3) 0.68940(19) 0.63699(12) 0.0332(5) Uani 1 1 d . . . . .
C5 C 0.0011(3) 0.7311(2) 0.59786(14) 0.0412(5) Uani 1 1 d . . . . .
H5 H -0.0931 0.6946 0.6056 0.049 Uiso 1 1 calc R . . . .
C6 C 0.0141(3) 0.8259(3) 0.54794(16) 0.0528(7) Uani 1 1 d . . . . .
H6 H -0.0710 0.8518 0.5217 0.063 Uiso 1 1 calc R . . . .
C7 C 0.1522(3) 0.8823(2) 0.53674(16) 0.0520(7) Uani 1 1 d . . . . .
H7 H 0.1615 0.9468 0.5035 0.062 Uiso 1 1 calc R . . . .
C8 C 0.2751(3) 0.8413(2) 0.57564(14) 0.0419(5) Uani 1 1 d . . . . .
C9 C 0.2714(3) 0.74434(19) 0.62603(12) 0.0328(5) Uani 1 1 d . . . . .
C10 C 0.4139(2) 0.7102(2) 0.66265(13) 0.0345(5) Uani 1 1 d . . . . .
H10 H 0.4852 0.7724 0.6684 0.041 Uiso 1 1 calc R . . . .
C11 C 0.4537(2) 0.6002(2) 0.68879(13) 0.0328(5) Uani 1 1 d . . . . .
C12 C 0.3569(2) 0.48658(19) 0.68239(14) 0.0338(5) Uani 1 1 d . . . . .
H12 H 0.4055 0.4222 0.7118 0.041 Uiso 1 1 calc R . . . .
C13 C 0.3498(3) 0.4417(2) 0.60219(14) 0.0395(5) Uani 1 1 d . . . . .
H13B H 0.3108 0.5075 0.5715 0.047 Uiso 1 1 calc R . . . .
H13A H 0.4524 0.4239 0.5857 0.047 Uiso 1 1 calc R . . . .
C14 C 0.2514(3) 0.3282(2) 0.59009(15) 0.0492(6) Uani 1 1 d . . . . .
H14A H 0.2936 0.2601 0.6177 0.059 Uiso 1 1 calc R . . . .
H14B H 0.1496 0.3436 0.6085 0.059 Uiso 1 1 calc R . . . .
C15 C 0.2438(3) 0.2951(2) 0.50915(15) 0.0443(6) Uani 1 1 d . . . . .
C16 C 0.3034(4) 0.1865(2) 0.48307(19) 0.0563(7) Uani 1 1 d . . . . .
H16 H 0.3481 0.1322 0.5161 0.068 Uiso 1 1 calc R . . . .
C17 C 0.2980(4) 0.1565(3) 0.4082(2) 0.0740(10) Uani 1 1 d . . . . .
H17 H 0.3401 0.0834 0.3915 0.089 Uiso 1 1 calc R . . . .
C18 C 0.2304(4) 0.2352(4) 0.35931(19) 0.0765(10) Uani 1 1 d . . . . .
H18 H 0.2253 0.2153 0.3094 0.092 Uiso 1 1 calc R . . . .
C19 C 0.1704(4) 0.3430(4) 0.38396(19) 0.0728(10) Uani 1 1 d . . . . .
H19 H 0.1248 0.3966 0.3507 0.087 Uiso 1 1 calc R . . . .
C20 C 0.1770(3) 0.3728(3) 0.45849(17) 0.0575(7) Uani 1 1 d . . . . .
H20 H 0.1357 0.4465 0.4746 0.069 Uiso 1 1 calc R . . . .
C21 C 0.6064(2) 0.5813(2) 0.72434(14) 0.0373(5) 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
C1 H1 0.9300 . ?
C1 N1 1.373(3) . ?
C1 C2 1.355(3) . ?
F1 C8 1.355(3) . ?
N1 C3 1.353(3) . ?
N1 C12 1.473(3) . ?
O1 C21 1.216(3) . ?
C2 H2A 0.9300 . ?
C2 N2 1.366(3) . ?
N2 C3 1.337(3) . ?
O2 H2 0.8200 . ?
O2 C21 1.303(3) . ?
C3 C4 1.460(3) . ?
C4 C5 1.398(3) . ?
C4 C9 1.411(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.365(4) . ?
C8 C9 1.398(3) . ?
C9 C10 1.466(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.339(3) . ?
C11 C12 1.509(3) . ?
C11 C21 1.504(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.533(3) . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 C14 1.529(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.510(4) . ?
C15 C16 1.380(4) . ?
C15 C20 1.380(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.396(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.370(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.365(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(5) . ?
C20 H20 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
N1 C1 H1 127.0 . . ?
C2 C1 H1 127.0 . . ?
C2 C1 N1 106.1(2) . . ?
C1 N1 C12 124.53(19) . . ?
C3 N1 C1 108.30(18) . . ?
C3 N1 C12 127.02(19) . . ?
C1 C2 H2A 125.2 . . ?
C1 C2 N2 109.5(2) . . ?
N2 C2 H2A 125.2 . . ?
C3 N2 C2 106.98(19) . . ?
C21 O2 H2 109.5 . . ?
N1 C3 C4 126.28(19) . . ?
N2 C3 N1 109.14(19) . . ?
N2 C3 C4 124.57(19) . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C9 120.2(2) . . ?
C9 C4 C3 122.21(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.4(2) . . ?
C8 C7 H7 120.8 . . ?
F1 C8 C7 118.0(2) . . ?
F1 C8 C9 117.5(2) . . ?
C7 C8 C9 124.5(2) . . ?
C4 C9 C10 126.34(19) . . ?
C8 C9 C4 115.8(2) . . ?
C8 C9 C10 117.9(2) . . ?
C9 C10 H10 116.2 . . ?
C11 C10 C9 127.7(2) . . ?
C11 C10 H10 116.2 . . ?
C10 C11 C12 124.4(2) . . ?
C10 C11 C21 120.5(2) . . ?
C21 C11 C12 115.03(19) . . ?
N1 C12 C11 110.62(17) . . ?
N1 C12 H12 107.6 . . ?
N1 C12 C13 112.13(18) . . ?
C11 C12 H12 107.6 . . ?
C11 C12 C13 111.00(19) . . ?
C13 C12 H12 107.6 . . ?
C12 C13 H13B 108.6 . . ?
C12 C13 H13A 108.6 . . ?
H13B C13 H13A 107.6 . . ?
C14 C13 C12 114.7(2) . . ?
C14 C13 H13B 108.6 . . ?
C14 C13 H13A 108.6 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.0(2) . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C16 C15 C14 121.4(3) . . ?
C20 C15 C14 121.1(2) . . ?
C20 C15 C16 117.6(3) . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.5(3) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 121.3(3) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
O1 C21 O2 124.4(2) . . ?
O1 C21 C11 120.7(2) . . ?
O2 C21 C11 114.9(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
C1 N1 C3 N2 -0.8(3) . . . . ?
C1 N1 C3 C4 -179.7(2) . . . . ?
C1 N1 C12 C11 -126.8(2) . . . . ?
C1 N1 C12 C13 108.7(2) . . . . ?
C1 C2 N2 C3 0.0(3) . . . . ?
F1 C8 C9 C4 179.3(2) . . . . ?
F1 C8 C9 C10 -0.1(3) . . . . ?
N1 C1 C2 N2 -0.4(3) . . . . ?
N1 C3 C4 C5 150.7(2) . . . . ?
N1 C3 C4 C9 -33.6(3) . . . . ?
N1 C12 C13 C14 -54.5(3) . . . . ?
C2 C1 N1 C3 0.7(3) . . . . ?
C2 C1 N1 C12 -175.0(2) . . . . ?
C2 N2 C3 N1 0.5(3) . . . . ?
C2 N2 C3 C4 179.4(2) . . . . ?
N2 C3 C4 C5 -28.0(3) . . . . ?
N2 C3 C4 C9 147.6(2) . . . . ?
C3 N1 C12 C11 58.3(3) . . . . ?
C3 N1 C12 C13 -66.2(3) . . . . ?
C3 C4 C5 C6 176.0(2) . . . . ?
C3 C4 C9 C8 -174.6(2) . . . . ?
C3 C4 C9 C10 4.7(3) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C4 C9 C10 C11 28.4(4) . . . . ?
C5 C4 C9 C8 0.9(3) . . . . ?
C5 C4 C9 C10 -179.7(2) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 F1 179.9(3) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C7 C8 C9 C4 -1.4(4) . . . . ?
C7 C8 C9 C10 179.2(3) . . . . ?
C8 C9 C10 C11 -152.3(2) . . . . ?
C9 C4 C5 C6 0.3(4) . . . . ?
C9 C10 C11 C12 2.4(4) . . . . ?
C9 C10 C11 C21 179.3(2) . . . . ?
C10 C11 C12 N1 -54.9(3) . . . . ?
C10 C11 C12 C13 70.3(3) . . . . ?
C10 C11 C21 O1 163.7(2) . . . . ?
C10 C11 C21 O2 -16.8(3) . . . . ?
C11 C12 C13 C14 -178.8(2) . . . . ?
C12 N1 C3 N2 174.8(2) . . . . ?
C12 N1 C3 C4 -4.1(4) . . . . ?
C12 C11 C21 O1 -19.0(3) . . . . ?
C12 C11 C21 O2 160.5(2) . . . . ?
C12 C13 C14 C15 176.7(2) . . . . ?
C13 C14 C15 C16 115.7(3) . . . . ?
C13 C14 C15 C20 -64.2(3) . . . . ?
C14 C15 C16 C17 -179.2(3) . . . . ?
C14 C15 C20 C19 179.7(3) . . . . ?
C15 C16 C17 C18 -0.9(5) . . . . ?
C16 C15 C20 C19 -0.2(4) . . . . ?
C16 C17 C18 C19 0.8(6) . . . . ?
C17 C18 C19 C20 -0.3(6) . . . . ?
C18 C19 C20 C15 0.0(5) . . . . ?
C20 C15 C16 C17 0.6(4) . . . . ?
C21 C11 C12 N1 128.0(2) . . . . ?
C21 C11 C12 C13 -106.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.821
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1936485'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan' 'Henan Normal University'
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-09-17 downloaded from the CCDC.
;
_audit_creation_date             2019-04-09
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N2 O'
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           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                   11.2543(4)
_cell_length_b                   11.6498(3)
_cell_length_c                   23.6897(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3105.97(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4687
_cell_measurement_temperature    295.01(13)
_cell_measurement_theta_max      26.6240
_cell_measurement_theta_min      3.8960
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14916
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.677
_diffrn_reflns_theta_min         3.498
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.01(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00  49.00   1.00   17.50    --   10.83-148.00 171.00   26
  2  ω    -56.00  23.00   1.00   17.50    --   10.83 -56.00-151.00   79
  3  ω     -8.00  28.00   1.00   17.50    --   10.83 -99.00 150.00   36
  4  ω    -20.00  29.00   1.00   17.50    --  -11.77 -99.00 -90.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0153447000
_diffrn_orient_matrix_UB_12      -0.0072304000
_diffrn_orient_matrix_UB_13      0.0288260000
_diffrn_orient_matrix_UB_21      0.0445921000
_diffrn_orient_matrix_UB_22      0.0399922000
_diffrn_orient_matrix_UB_23      0.0077982000
_diffrn_orient_matrix_UB_31      -0.0418175000
_diffrn_orient_matrix_UB_32      0.0453066000
_diffrn_orient_matrix_UB_33      -0.0022915000
_diffrn_oxdiff_digest_frames     
;
01fd981e54672e879db198d13c57a8b8b900027d7c3
;
_diffrn_oxdiff_digest_hkl        
;
0129cff6298eae9eacbd4c4381bd5635f36a22
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                2603
_reflns_number_total             3768
_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 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3768
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.059
_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)+(0.0501P)²+0.8864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1336
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C21(H21)
;
_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
C1 C 0.60571(17) 0.31421(15) 0.49402(7) 0.0386(4) Uani 1 1 d . . . . .
C2 C 0.70356(16) 0.35659(13) 0.45720(6) 0.0339(4) Uani 1 1 d . . . . .
C3 C 0.71214(18) 0.31085(15) 0.40295(7) 0.0423(4) Uani 1 1 d . . . . .
H3 H 0.6583 0.2550 0.3915 0.051 Uiso 1 1 calc R . . . .
C4 C 0.7991(2) 0.34701(17) 0.36596(8) 0.0503(5) Uani 1 1 d . . . . .
H4 H 0.8043 0.3157 0.3299 0.060 Uiso 1 1 calc R . . . .
C5 C 0.8776(2) 0.42945(18) 0.38304(8) 0.0551(5) Uani 1 1 d . . . . .
H5 H 0.9371 0.4536 0.3586 0.066 Uiso 1 1 calc R . . . .
C6 C 0.86950(19) 0.47759(16) 0.43633(8) 0.0478(5) Uani 1 1 d . . . . .
H6 H 0.9234 0.5342 0.4469 0.057 Uiso 1 1 calc R . . . .
C7 C 0.78266(16) 0.44306(13) 0.47436(7) 0.0347(4) Uani 1 1 d . . . . .
C8 C 0.77247(19) 0.50401(13) 0.53066(7) 0.0400(4) Uani 1 1 d . . . . .
H8A H 0.6919 0.5324 0.5347 0.048 Uiso 1 1 calc R . . . .
H8B H 0.8250 0.5700 0.5302 0.048 Uiso 1 1 calc R . . . .
C9 C 0.80234(16) 0.43064(13) 0.58246(7) 0.0350(4) Uani 1 1 d . . . . .
H9A H 0.8879 0.4234 0.5859 0.042 Uiso 1 1 calc R . . . .
H9B H 0.7728 0.4682 0.6162 0.042 Uiso 1 1 calc R . . . .
C10 C 0.74701(14) 0.31181(12) 0.57749(6) 0.0279(3) Uani 1 1 d . . . . .
H10 H 0.7926 0.2708 0.5486 0.034 Uiso 1 1 calc R . . . .
C11 C 0.62141(15) 0.31780(13) 0.55643(6) 0.0313(4) Uani 1 1 d . . . . .
C12 C 0.52473(16) 0.33969(14) 0.58727(7) 0.0365(4) Uani 1 1 d . . . . .
H12 H 0.4543 0.3430 0.5668 0.044 Uiso 1 1 calc R . . . .
C13 C 0.51121(15) 0.35926(13) 0.64773(7) 0.0343(4) Uani 1 1 d . . . . .
C14 C 0.41068(18) 0.42187(16) 0.66413(8) 0.0464(5) Uani 1 1 d . . . . .
H14 H 0.3596 0.4499 0.6365 0.056 Uiso 1 1 calc R . . . .
C15 C 0.3857(2) 0.44295(17) 0.71987(9) 0.0538(5) Uani 1 1 d . . . . .
H15 H 0.3197 0.4866 0.7298 0.065 Uiso 1 1 calc R . . . .
C16 C 0.4590(2) 0.39886(17) 0.76066(9) 0.0543(5) Uani 1 1 d . . . . .
H16 H 0.4412 0.4108 0.7985 0.065 Uiso 1 1 calc R . . . .
C17 C 0.55894(19) 0.33694(15) 0.74615(8) 0.0459(5) Uani 1 1 d . . . . .
H17 H 0.6078 0.3081 0.7745 0.055 Uiso 1 1 calc R . . . .
C18 C 0.58806(16) 0.31678(13) 0.68956(7) 0.0334(4) Uani 1 1 d . . . . .
C19 C 0.69462(16) 0.24835(13) 0.67868(6) 0.0325(4) Uani 1 1 d . . . . .
C20 C 0.84284(18) 0.13636(14) 0.69320(7) 0.0429(5) Uani 1 1 d . . . . .
H20 H 0.8951 0.0862 0.7110 0.052 Uiso 1 1 calc R . . . .
C21 C 0.85516(16) 0.17470(13) 0.63963(7) 0.0360(4) Uani 1 1 d . . . . .
H21 H 0.9158 0.1567 0.6145 0.043 Uiso 1 1 calc R . . . .
N1 N 0.74346(15) 0.18130(12) 0.71761(6) 0.0426(4) Uani 1 1 d . . . . .
N2 N 0.75982(12) 0.24562(10) 0.62994(5) 0.0296(3) Uani 1 1 d . . . . .
O1 O 0.51411(13) 0.27689(15) 0.47309(6) 0.0677(5) 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
C1 C2 1.489(2) . ?
C1 C11 1.489(2) . ?
C1 O1 1.224(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.405(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(2) . ?
C7 C8 1.515(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.533(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.522(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.501(2) . ?
C10 N2 1.4694(18) . ?
C11 C12 1.335(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.458(2) . ?
C13 C14 1.401(2) . ?
C13 C18 1.405(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.400(2) . ?
C18 C19 1.463(2) . ?
C19 N1 1.328(2) . ?
C19 N2 1.369(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.353(2) . ?
C20 N1 1.364(2) . ?
C21 H21 0.9300 . ?
C21 N2 1.374(2) . ?

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
C2 C1 C11 118.97(15) . . ?
O1 C1 C2 120.22(15) . . ?
O1 C1 C11 120.81(16) . . ?
C3 C2 C1 117.67(16) . . ?
C3 C2 C7 119.80(16) . . ?
C7 C2 C1 122.48(14) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.18(18) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.03(17) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.85(19) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.36(19) . . ?
C7 C6 H6 119.3 . . ?
C2 C7 C8 122.88(15) . . ?
C6 C7 C2 117.77(16) . . ?
C6 C7 C8 119.25(16) . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
C7 C8 C9 115.26(13) . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 C8 110.83(13) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C9 C10 H10 106.5 . . ?
C11 C10 C9 111.64(13) . . ?
C11 C10 H10 106.5 . . ?
N2 C10 C9 111.82(12) . . ?
N2 C10 H10 106.5 . . ?
N2 C10 C11 113.45(13) . . ?
C1 C11 C10 116.14(14) . . ?
C12 C11 C1 116.86(15) . . ?
C12 C11 C10 126.47(14) . . ?
C11 C12 H12 114.6 . . ?
C11 C12 C13 130.72(16) . . ?
C13 C12 H12 114.6 . . ?
C14 C13 C12 115.97(16) . . ?
C14 C13 C18 119.00(16) . . ?
C18 C13 C12 124.99(15) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.71(19) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.20(19) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.74(18) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.14(19) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C19 124.90(14) . . ?
C17 C18 C13 118.18(16) . . ?
C17 C18 C19 116.87(16) . . ?
N1 C19 C18 122.52(14) . . ?
N1 C19 N2 110.52(15) . . ?
N2 C19 C18 126.93(14) . . ?
C21 C20 H20 124.6 . . ?
C21 C20 N1 110.81(15) . . ?
N1 C20 H20 124.6 . . ?
C20 C21 H21 127.0 . . ?
C20 C21 N2 105.98(16) . . ?
N2 C21 H21 127.0 . . ?
C19 N1 C20 105.71(14) . . ?
C19 N2 C10 130.44(13) . . ?
C19 N2 C21 106.97(13) . . ?
C21 N2 C10 122.24(13) . . ?

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
C1 C2 C3 C4 178.94(16) . . . . ?
C1 C2 C7 C6 -178.92(16) . . . . ?
C1 C2 C7 C8 -2.5(3) . . . . ?
C1 C11 C12 C13 -173.74(16) . . . . ?
C2 C1 C11 C10 -27.0(2) . . . . ?
C2 C1 C11 C12 145.22(16) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C7 C8 C9 69.9(2) . . . . ?
C3 C2 C7 C6 -1.7(2) . . . . ?
C3 C2 C7 C8 174.65(15) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C5 C6 C7 C8 -175.91(17) . . . . ?
C6 C7 C8 C9 -113.77(18) . . . . ?
C7 C2 C3 C4 1.6(3) . . . . ?
C7 C8 C9 C10 -43.3(2) . . . . ?
C8 C9 C10 C11 -43.54(18) . . . . ?
C8 C9 C10 N2 -171.86(14) . . . . ?
C9 C10 C11 C1 89.19(16) . . . . ?
C9 C10 C11 C12 -82.17(19) . . . . ?
C9 C10 N2 C19 81.2(2) . . . . ?
C9 C10 N2 C21 -91.18(17) . . . . ?
C10 C11 C12 C13 -2.4(3) . . . . ?
C11 C1 C2 C3 153.30(16) . . . . ?
C11 C1 C2 C7 -29.4(2) . . . . ?
C11 C10 N2 C19 -46.2(2) . . . . ?
C11 C10 N2 C21 141.48(15) . . . . ?
C11 C12 C13 C14 156.22(18) . . . . ?
C11 C12 C13 C18 -26.3(3) . . . . ?
C12 C13 C14 C15 177.86(17) . . . . ?
C12 C13 C18 C17 -176.04(16) . . . . ?
C12 C13 C18 C19 1.3(3) . . . . ?
C13 C14 C15 C16 -1.9(3) . . . . ?
C13 C18 C19 N1 -158.67(16) . . . . ?
C13 C18 C19 N2 23.6(3) . . . . ?
C14 C13 C18 C17 1.4(2) . . . . ?
C14 C13 C18 C19 178.73(15) . . . . ?
C14 C15 C16 C17 2.0(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C13 -1.4(3) . . . . ?
C16 C17 C18 C19 -178.88(16) . . . . ?
C17 C18 C19 N1 18.7(2) . . . . ?
C17 C18 C19 N2 -159.04(16) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C18 C19 N1 C20 -177.18(15) . . . . ?
C18 C19 N2 C10 3.6(3) . . . . ?
C18 C19 N2 C21 176.82(15) . . . . ?
C20 C21 N2 C10 174.82(14) . . . . ?
C20 C21 N2 C19 0.88(18) . . . . ?
C21 C20 N1 C19 -0.3(2) . . . . ?
N1 C19 N2 C10 -174.37(15) . . . . ?
N1 C19 N2 C21 -1.11(18) . . . . ?
N1 C20 C21 N2 -0.4(2) . . . . ?
N2 C10 C11 C1 -143.36(13) . . . . ?
N2 C10 C11 C12 45.3(2) . . . . ?
N2 C19 N1 C20 0.87(19) . . . . ?
O1 C1 C2 C3 -26.5(2) . . . . ?
O1 C1 C2 C7 150.72(18) . . . . ?
O1 C1 C11 C10 152.85(17) . . . . ?
O1 C1 C11 C12 -34.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.718
_oxdiff_exptl_absorpt_empirical_full_min 0.668
####################################################################### 
# 
# 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_3g
_database_code_depnum_ccdc_archive 'CCDC 1936480'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-09-17 downloaded from the CCDC.
;
_audit_creation_date             2019-06-25
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Br N2 O2, C2 H6 O S'
_chemical_formula_sum            'C23 H23 Br N2 O3 S'
_chemical_formula_weight         487.40
_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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 '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                   8.7087(6)
_cell_length_b                   24.8530(16)
_cell_length_c                   10.4060(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.876(8)
_cell_angle_gamma                90
_cell_volume                     2104.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4880
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      28.1940
_cell_measurement_theta_min      3.8980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13912
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.184
_diffrn_reflns_theta_min         3.510
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  35.00   1.00   12.22    --   15.82 -38.00 150.00   88
  2  ω     -1.00  83.00   1.00   12.22    --   15.82  57.00 -30.00   84
  3  ω    -78.00 -31.00   1.00   12.22    --  -17.23 138.00 141.00   47
  4  ω    -85.00   8.00   1.00   12.22    --  -17.23 -77.00 -30.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137141000
_diffrn_orient_matrix_UB_12      -0.0103710000
_diffrn_orient_matrix_UB_13      0.0584436000
_diffrn_orient_matrix_UB_21      -0.0030509000
_diffrn_orient_matrix_UB_22      0.0265774000
_diffrn_orient_matrix_UB_23      0.0238216000
_diffrn_orient_matrix_UB_31      -0.0860816000
_diffrn_orient_matrix_UB_32      0.0007161000
_diffrn_orient_matrix_UB_33      -0.0365874000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                4128
_reflns_number_total             4931
_reflns_odcompleteness_completeness 99.66
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.245
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4931
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.056
_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)+(0.0353P)²+2.6020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0936
_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 C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C4(H4), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17),
 C18(H18), C20(H20)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1 Br 1.19089(3) 0.42773(2) 0.83000(3) 0.02186(9) Uani 1 1 d . . . . .
O1 O 0.3529(2) 0.50047(7) 0.31337(19) 0.0203(4) Uani 1 1 d . . . . .
O2 O 0.2702(2) 0.43207(7) 0.16417(18) 0.0169(4) Uani 1 1 d . . . . .
H2 H 0.1789 0.4407 0.1631 0.025 Uiso 1 1 calc GR . . . .
N1 N 0.7116(2) 0.42744(8) 0.1198(2) 0.0116(4) Uani 1 1 d . . . . .
N2 N 0.9637(2) 0.44048(8) 0.1261(2) 0.0139(4) Uani 1 1 d . . . . .
C1 C 1.1011(3) 0.41055(10) 0.4149(3) 0.0149(5) Uani 1 1 d . . . . .
H1 H 1.1598 0.3995 0.3604 0.018 Uiso 1 1 calc R . . . .
C2 C 1.1776(3) 0.41084(10) 0.5559(3) 0.0155(5) Uani 1 1 d . . . . .
H2A H 1.2866 0.4001 0.5964 0.019 Uiso 1 1 calc R . . . .
C3 C 1.0892(3) 0.42737(10) 0.6360(2) 0.0154(5) Uani 1 1 d . . . . .
C4 C 0.9274(3) 0.44337(10) 0.5774(2) 0.0131(5) Uani 1 1 d . . . . .
H4 H 0.8712 0.4549 0.6335 0.016 Uiso 1 1 calc R . . . .
C5 C 0.8470(3) 0.44249(9) 0.4345(2) 0.0117(5) Uani 1 1 d . . . . .
C6 C 0.9368(3) 0.42656(9) 0.3518(2) 0.0123(5) Uani 1 1 d . . . . .
C7 C 0.8722(3) 0.43058(9) 0.2023(2) 0.0111(4) Uani 1 1 d . . . . .
C8 C 0.8573(3) 0.44436(10) -0.0079(3) 0.0161(5) Uani 1 1 d . . . . .
H8 H 0.8876 0.4514 -0.0834 0.019 Uiso 1 1 calc R . . . .
C9 C 0.7016(3) 0.43641(9) -0.0127(2) 0.0140(5) Uani 1 1 d . . . . .
H9 H 0.6066 0.4369 -0.0906 0.017 Uiso 1 1 calc R . . . .
C10 C 0.6742(3) 0.45941(9) 0.3850(2) 0.0122(5) Uani 1 1 d . . . . .
H10 H 0.6448 0.4826 0.4426 0.015 Uiso 1 1 calc R . . . .
C11 C 0.5535(3) 0.44598(9) 0.2682(2) 0.0114(5) Uani 1 1 d . . . . .
C12 C 0.5732(3) 0.40975(10) 0.1587(2) 0.0121(5) Uani 1 1 d . . . . .
H12 H 0.4734 0.4135 0.0770 0.015 Uiso 1 1 calc R . . . .
C13 C 0.5893(3) 0.35024(10) 0.1988(3) 0.0151(5) Uani 1 1 d . . . . .
H13A H 0.6915 0.3447 0.2753 0.018 Uiso 1 1 calc R . . . .
H13B H 0.4997 0.3403 0.2288 0.018 Uiso 1 1 calc R . . . .
C14 C 0.5863(3) 0.31420(10) 0.0796(3) 0.0209(6) Uani 1 1 d . . . . .
H14A H 0.4868 0.3218 0.0019 0.025 Uiso 1 1 calc R . . . .
H14B H 0.6787 0.3238 0.0528 0.025 Uiso 1 1 calc R . . . .
C15 C 0.5934(3) 0.25458(10) 0.1073(3) 0.0196(5) Uani 1 1 d . . . . .
C16 C 0.5056(4) 0.21943(12) 0.0033(3) 0.0275(6) Uani 1 1 d . . . . .
H16 H 0.4388 0.2331 -0.0814 0.033 Uiso 1 1 calc R . . . .
C17 C 0.5162(4) 0.16424(12) 0.0240(3) 0.0324(7) Uani 1 1 d . . . . .
H17 H 0.4567 0.1414 -0.0470 0.039 Uiso 1 1 calc R . . . .
C18 C 0.6132(4) 0.14296(11) 0.1481(3) 0.0301(7) Uani 1 1 d . . . . .
H18 H 0.6212 0.1059 0.1610 0.036 Uiso 1 1 calc R . . . .
C19 C 0.6985(4) 0.17723(13) 0.2532(4) 0.0351(7) Uani 1 1 d . . . . .
C20 C 0.6884(4) 0.23262(12) 0.2325(3) 0.0310(7) Uani 1 1 d . . . . .
H20 H 0.7467 0.2553 0.3043 0.037 Uiso 1 1 calc R . . . .
C21 C 0.3816(3) 0.46293(10) 0.2508(2) 0.0130(5) Uani 1 1 d . . . . .
H19 H 0.772(3) 0.1636(11) 0.347(3) 0.016 Uiso 1 1 d R . . . .
S1 S 1.00668(10) 0.22138(3) 0.61415(9) 0.03416(19) Uani 1 1 d . . . . .
O3 O 1.0713(4) 0.20941(11) 0.7639(3) 0.0598(8) Uani 1 1 d . . . . .
C22 C 1.1564(5) 0.20085(16) 0.5483(4) 0.0517(10) Uani 1 1 d . . . . .
H22A H 1.2601 0.2168 0.6014 0.078 Uiso 1 1 calc GR . . . .
H22B H 1.1252 0.2122 0.4542 0.078 Uiso 1 1 calc GR . . . .
H22C H 1.1661 0.1624 0.5532 0.078 Uiso 1 1 calc GR . . . .
C23 C 1.0252(6) 0.29108(14) 0.5938(5) 0.0596(12) Uani 1 1 d . . . . .
H23A H 0.9460 0.3098 0.6220 0.089 Uiso 1 1 calc GR . . . .
H23B H 1.0058 0.2989 0.4990 0.089 Uiso 1 1 calc GR . . . .
H23C H 1.1338 0.3026 0.6494 0.089 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.894(2) . ?
O1 C21 1.214(3) . ?
O2 H2 0.8200 . ?
O2 C21 1.311(3) . ?
N1 C7 1.358(3) . ?
N1 C9 1.368(3) . ?
N1 C12 1.469(3) . ?
N2 C7 1.333(3) . ?
N2 C8 1.376(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(3) . ?
C1 C6 1.403(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.383(3) . ?
C3 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(3) . ?
C5 C6 1.410(3) . ?
C5 C10 1.468(3) . ?
C6 C7 1.457(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.354(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.335(3) . ?
C11 C12 1.509(3) . ?
C11 C21 1.503(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.529(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.523(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.506(4) . ?
C15 C16 1.389(4) . ?
C15 C20 1.382(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(4) . ?
C19 C20 1.391(4) . ?
C19 H19 1.02(3) . ?
C20 H20 0.9300 . ?
S1 O3 1.486(3) . ?
S1 C22 1.751(4) . ?
S1 C23 1.759(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C21 O2 H2 109.5 . . ?
C7 N1 C9 108.02(19) . . ?
C7 N1 C12 127.2(2) . . ?
C9 N1 C12 124.23(19) . . ?
C7 N2 C8 106.6(2) . . ?
C2 C1 H1 119.3 . . ?
C2 C1 C6 121.5(2) . . ?
C6 C1 H1 119.3 . . ?
C1 C2 H2A 120.6 . . ?
C1 C2 C3 118.8(2) . . ?
C3 C2 H2A 120.6 . . ?
C2 C3 Br1 119.66(18) . . ?
C4 C3 Br1 119.05(19) . . ?
C4 C3 C2 121.3(2) . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 118.4(2) . . ?
C4 C5 C10 115.5(2) . . ?
C6 C5 C10 126.0(2) . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C7 117.4(2) . . ?
C5 C6 C7 123.0(2) . . ?
N1 C7 C6 126.2(2) . . ?
N2 C7 N1 109.5(2) . . ?
N2 C7 C6 124.2(2) . . ?
N2 C8 H8 125.3 . . ?
C9 C8 N2 109.3(2) . . ?
C9 C8 H8 125.3 . . ?
N1 C9 H9 126.8 . . ?
C8 C9 N1 106.5(2) . . ?
C8 C9 H9 126.8 . . ?
C5 C10 H10 115.7 . . ?
C11 C10 C5 128.6(2) . . ?
C11 C10 H10 115.7 . . ?
C10 C11 C12 124.9(2) . . ?
C10 C11 C21 117.8(2) . . ?
C21 C11 C12 116.9(2) . . ?
N1 C12 C11 110.77(19) . . ?
N1 C12 H12 107.1 . . ?
N1 C12 C13 111.12(19) . . ?
C11 C12 H12 107.1 . . ?
C11 C12 C13 113.2(2) . . ?
C13 C12 H12 107.1 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 111.9(2) . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C13 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 C13 115.8(2) . . ?
C15 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C16 C15 C14 119.7(3) . . ?
C20 C15 C14 122.6(2) . . ?
C20 C15 C16 117.7(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.1(3) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 122.3(16) . . ?
C20 C19 H19 117.5(16) . . ?
C15 C20 C19 121.3(3) . . ?
C15 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
O1 C21 O2 125.1(2) . . ?
O1 C21 C11 122.5(2) . . ?
O2 C21 C11 112.4(2) . . ?
O3 S1 C22 107.17(19) . . ?
O3 S1 C23 107.84(19) . . ?
C22 S1 C23 97.3(2) . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
Br1 C3 C4 C5 -178.55(18) . . . . ?
N1 C12 C13 C14 -62.1(3) . . . . ?
N2 C8 C9 N1 -0.1(3) . . . . ?
C1 C2 C3 Br1 179.60(19) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C6 C7 N1 156.5(2) . . . . ?
C1 C6 C7 N2 -26.7(3) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C2 C1 C6 C7 173.4(2) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -2.0(3) . . . . ?
C3 C4 C5 C10 178.8(2) . . . . ?
C4 C5 C6 C1 2.0(3) . . . . ?
C4 C5 C6 C7 -172.1(2) . . . . ?
C4 C5 C10 C11 -154.3(2) . . . . ?
C5 C6 C7 N1 -29.4(4) . . . . ?
C5 C6 C7 N2 147.4(2) . . . . ?
C5 C10 C11 C12 -1.0(4) . . . . ?
C5 C10 C11 C21 171.8(2) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C6 C5 C10 C11 26.6(4) . . . . ?
C7 N1 C9 C8 0.6(3) . . . . ?
C7 N1 C12 C11 61.3(3) . . . . ?
C7 N1 C12 C13 -65.5(3) . . . . ?
C7 N2 C8 C9 -0.4(3) . . . . ?
C8 N2 C7 N1 0.8(3) . . . . ?
C8 N2 C7 C6 -176.5(2) . . . . ?
C9 N1 C7 N2 -0.8(3) . . . . ?
C9 N1 C7 C6 176.3(2) . . . . ?
C9 N1 C12 C11 -128.4(2) . . . . ?
C9 N1 C12 C13 104.8(2) . . . . ?
C10 C5 C6 C1 -178.9(2) . . . . ?
C10 C5 C6 C7 7.0(4) . . . . ?
C10 C11 C12 N1 -50.9(3) . . . . ?
C10 C11 C12 C13 74.8(3) . . . . ?
C10 C11 C21 O1 23.1(4) . . . . ?
C10 C11 C21 O2 -155.5(2) . . . . ?
C11 C12 C13 C14 172.5(2) . . . . ?
C12 N1 C7 N2 170.7(2) . . . . ?
C12 N1 C7 C6 -12.1(4) . . . . ?
C12 N1 C9 C8 -171.3(2) . . . . ?
C12 C11 C21 O1 -163.5(2) . . . . ?
C12 C11 C21 O2 17.9(3) . . . . ?
C12 C13 C14 C15 -177.2(2) . . . . ?
C13 C14 C15 C16 144.1(3) . . . . ?
C13 C14 C15 C20 -37.7(4) . . . . ?
C14 C15 C16 C17 176.9(3) . . . . ?
C14 C15 C20 C19 -177.0(3) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C15 C20 C19 1.2(5) . . . . ?
C16 C17 C18 C19 1.0(5) . . . . ?
C17 C18 C19 C20 -1.2(5) . . . . ?
C18 C19 C20 C15 0.0(5) . . . . ?
C20 C15 C16 C17 -1.4(4) . . . . ?
C21 C11 C12 N1 136.3(2) . . . . ?
C21 C11 C12 C13 -98.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.772
