# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_exp_8996
_database_code_depnum_ccdc_archive 'CCDC 2342463'
loop_
_audit_author_name
_audit_author_address
'Yu Xiong'
;Shenzhen University
China
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2021-01-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 Br2 N O'
_chemical_formula_sum            'C20 H13 Br2 N O'
_chemical_formula_weight         443.13
_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'

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

_cell_length_a                   7.0974(6)
_cell_length_b                   21.6508(15)
_cell_length_c                   10.7738(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.688(8)
_cell_angle_gamma                90
_cell_volume                     1640.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1420
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8600
_cell_measurement_theta_min      3.2330
_shelx_estimated_absorpt_T_max   0.524
_shelx_estimated_absorpt_T_min   0.300
_exptl_absorpt_coefficient_mu    4.947
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7182
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.127
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  37.00   1.00    5.00    --  -16.28   0.00  60.00   34
  2  ω    -17.00  22.00   1.00    5.00    --  -16.28 -99.00   0.00   39
  3  ω     -4.00  53.00   1.00    5.00    --   15.49 -99.00-120.00   57
  4  ω    -85.00  -3.00   1.00    5.00    --  -16.28 -37.00   0.00   82
  5  ω    -86.00 -61.00   1.00    5.00    --  -16.28   0.00  60.00   25
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0460416000
_diffrn_orient_matrix_UB_12      0.0017994000
_diffrn_orient_matrix_UB_13      -0.0543949000
_diffrn_orient_matrix_UB_21      -0.0010991000
_diffrn_orient_matrix_UB_22      -0.0326868000
_diffrn_orient_matrix_UB_23      -0.0044931000
_diffrn_orient_matrix_UB_31      -0.0896778000
_diffrn_orient_matrix_UB_32      0.0013084000
_diffrn_orient_matrix_UB_33      -0.0379137000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1991
_reflns_number_total             2894
_reflns_odcompleteness_completeness 99.88
_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       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2894
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.1392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1024
_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:
 C9(H9), C12(H12), C20(H20), C19(H19), C6(H6), C11(H11), C16(H16), C17(H17),
 C5(H5), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.58329(8) 0.56849(3) 0.12412(5) 0.0580(2) Uani 1 1 d . . . . .
Br2 Br 0.10576(8) 0.19535(2) 0.57189(7) 0.0652(2) Uani 1 1 d . . . . .
O1 O 0.9194(5) 0.39685(16) 0.7863(3) 0.0570(10) Uani 1 1 d . . . . .
N1 N 0.8220(5) 0.40878(16) 0.5783(4) 0.0334(10) Uani 1 1 d . . . . .
C8 C 0.7489(5) 0.5102(2) 0.4884(4) 0.0268(11) Uani 1 1 d . . . . .
C7 C 0.7914(5) 0.5370(2) 0.6128(4) 0.0280(10) Uani 1 1 d . . . . .
C13 C 0.7594(6) 0.4459(2) 0.4741(4) 0.0294(11) Uani 1 1 d . . . . .
C9 C 0.6955(6) 0.5455(2) 0.3820(4) 0.0316(11) Uani 1 1 d . . . . .
H9 H 0.6891 0.5882 0.3892 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6682(6) 0.3053(2) 0.5636(4) 0.0349(12) Uani 1 1 d . . . . .
C18 C 0.3363(6) 0.2392(2) 0.5677(5) 0.0387(12) Uani 1 1 d . . . . .
C12 C 0.7112(6) 0.4199(2) 0.3566(4) 0.0357(12) Uani 1 1 d . . . . .
H12 H 0.7145 0.3772 0.3476 0.043 Uiso 1 1 calc R U . . .
C10 C 0.6521(6) 0.5188(2) 0.2671(4) 0.0349(12) Uani 1 1 d . . . . .
C2 C 0.8468(6) 0.4985(2) 0.7144(4) 0.0353(12) Uani 1 1 d . . . . .
C20 C 0.5609(6) 0.3122(2) 0.6597(4) 0.0361(12) Uani 1 1 d . . . . .
H20 H 0.6016 0.3395 0.7245 0.043 Uiso 1 1 calc R U . . .
C1 C 0.8660(6) 0.4316(2) 0.6980(5) 0.0386(12) Uani 1 1 d . . . . .
C19 C 0.3946(7) 0.2798(2) 0.6626(5) 0.0442(13) Uani 1 1 d . . . . .
H19 H 0.3230 0.2854 0.7280 0.053 Uiso 1 1 calc R U . . .
C6 C 0.7786(6) 0.6005(2) 0.6359(4) 0.0373(12) Uani 1 1 d . . . . .
H6 H 0.7421 0.6275 0.5698 0.045 Uiso 1 1 calc R U . . .
C11 C 0.6586(6) 0.4562(2) 0.2535(5) 0.0415(13) Uani 1 1 d . . . . .
H11 H 0.6277 0.4383 0.1750 0.050 Uiso 1 1 calc R U . . .
C16 C 0.6066(7) 0.2637(2) 0.4705(5) 0.0445(13) Uani 1 1 d . . . . .
H16 H 0.6779 0.2583 0.4049 0.053 Uiso 1 1 calc R U . . .
C14 C 0.8486(6) 0.3418(2) 0.5634(5) 0.0405(12) Uani 1 1 d . . . . .
H14A H 0.9421 0.3272 0.6310 0.049 Uiso 1 1 calc R U . . .
H14B H 0.8985 0.3344 0.4852 0.049 Uiso 1 1 calc R U . . .
C17 C 0.4413(7) 0.2297(2) 0.4714(5) 0.0500(14) Uani 1 1 d . . . . .
H17 H 0.4027 0.2012 0.4085 0.060 Uiso 1 1 calc R U . . .
C5 C 0.8200(7) 0.6231(2) 0.7560(5) 0.0469(14) Uani 1 1 d . . . . .
H5 H 0.8105 0.6653 0.7700 0.056 Uiso 1 1 calc R U . . .
C3 C 0.8855(7) 0.5225(3) 0.8344(5) 0.0480(14) Uani 1 1 d . . . . .
H3 H 0.9193 0.4960 0.9016 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8748(7) 0.5846(3) 0.8552(5) 0.0538(15) Uani 1 1 d . . . . .
H4 H 0.9044 0.6005 0.9357 0.065 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.889(4) . ?
Br2 C18 1.897(5) . ?
O1 C1 1.232(5) . ?
N1 C13 1.404(5) . ?
N1 C1 1.377(6) . ?
N1 C14 1.474(5) . ?
C8 C7 1.455(6) . ?
C8 C13 1.403(6) . ?
C8 C9 1.388(6) . ?
C7 C2 1.391(6) . ?
C7 C6 1.402(6) . ?
C13 C12 1.386(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(6) . ?
C15 C20 1.373(6) . ?
C15 C16 1.374(6) . ?
C15 C14 1.505(6) . ?
C18 C19 1.369(6) . ?
C18 C17 1.372(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.371(6) . ?
C10 C11 1.364(6) . ?
C2 C1 1.468(6) . ?
C2 C3 1.386(6) . ?
C20 H20 0.9300 . ?
C20 C19 1.377(6) . ?
C19 H19 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.378(6) . ?
C11 H11 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.387(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C17 H17 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.370(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(7) . ?
C4 H4 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
C13 N1 C14 120.5(4) . . ?
C1 N1 C13 123.4(4) . . ?
C1 N1 C14 116.0(4) . . ?
C13 C8 C7 119.3(4) . . ?
C9 C8 C7 122.7(4) . . ?
C9 C8 C13 117.9(4) . . ?
C2 C7 C8 119.2(4) . . ?
C2 C7 C6 117.8(4) . . ?
C6 C7 C8 123.0(4) . . ?
C8 C13 N1 119.7(4) . . ?
C12 C13 N1 120.7(4) . . ?
C12 C13 C8 119.5(4) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.3(4) . . ?
C10 C9 H9 119.3 . . ?
C20 C15 C16 117.9(4) . . ?
C20 C15 C14 120.1(4) . . ?
C16 C15 C14 122.0(5) . . ?
C19 C18 Br2 118.6(4) . . ?
C19 C18 C17 121.3(5) . . ?
C17 C18 Br2 120.0(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 C13 121.0(4) . . ?
C11 C12 H12 119.5 . . ?
C9 C10 Br1 120.1(3) . . ?
C9 C10 C11 120.7(4) . . ?
C11 C10 Br1 119.2(4) . . ?
C7 C2 C1 121.2(4) . . ?
C3 C2 C7 120.6(4) . . ?
C3 C2 C1 118.2(5) . . ?
C15 C20 H20 119.2 . . ?
C15 C20 C19 121.6(4) . . ?
C19 C20 H20 119.2 . . ?
O1 C1 N1 120.8(4) . . ?
O1 C1 C2 122.2(4) . . ?
N1 C1 C2 117.0(4) . . ?
C18 C19 C20 119.0(5) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.2(5) . . ?
C5 C6 H6 119.9 . . ?
C12 C11 H11 120.3 . . ?
C10 C11 C12 119.5(4) . . ?
C10 C11 H11 120.3 . . ?
C15 C16 H16 119.0 . . ?
C15 C16 C17 121.9(5) . . ?
C17 C16 H16 119.0 . . ?
N1 C14 C15 113.3(4) . . ?
N1 C14 H14A 108.9 . . ?
N1 C14 H14B 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C18 C17 C16 118.1(5) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 H5 119.3 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 119.5 . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.4 . . ?

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 C10 C11 C12 179.0(3) . . . . ?
Br2 C18 C19 C20 -179.4(3) . . . . ?
Br2 C18 C17 C16 178.5(3) . . . . ?
N1 C13 C12 C11 -176.9(4) . . . . ?
C8 C7 C2 C1 1.0(6) . . . . ?
C8 C7 C2 C3 -179.0(4) . . . . ?
C8 C7 C6 C5 179.7(4) . . . . ?
C8 C13 C12 C11 1.9(7) . . . . ?
C8 C9 C10 Br1 -179.1(3) . . . . ?
C8 C9 C10 C11 0.5(7) . . . . ?
C7 C8 C13 N1 -4.0(6) . . . . ?
C7 C8 C13 C12 177.3(4) . . . . ?
C7 C8 C9 C10 -178.4(4) . . . . ?
C7 C2 C1 O1 178.2(4) . . . . ?
C7 C2 C1 N1 -1.6(6) . . . . ?
C7 C2 C3 C4 -1.6(7) . . . . ?
C7 C6 C5 C4 0.2(8) . . . . ?
C13 N1 C1 O1 179.6(4) . . . . ?
C13 N1 C1 C2 -0.6(6) . . . . ?
C13 N1 C14 C15 -84.4(5) . . . . ?
C13 C8 C7 C2 1.8(6) . . . . ?
C13 C8 C7 C6 -177.9(4) . . . . ?
C13 C8 C9 C10 0.8(6) . . . . ?
C13 C12 C11 C10 -0.6(7) . . . . ?
C9 C8 C7 C2 -179.0(4) . . . . ?
C9 C8 C7 C6 1.2(6) . . . . ?
C9 C8 C13 N1 176.8(4) . . . . ?
C9 C8 C13 C12 -1.9(6) . . . . ?
C9 C10 C11 C12 -0.6(7) . . . . ?
C15 C20 C19 C18 0.7(7) . . . . ?
C15 C16 C17 C18 1.2(7) . . . . ?
C2 C7 C6 C5 -0.1(6) . . . . ?
C2 C3 C4 C5 1.7(8) . . . . ?
C20 C15 C16 C17 0.3(7) . . . . ?
C20 C15 C14 N1 -52.9(6) . . . . ?
C1 N1 C13 C8 3.5(6) . . . . ?
C1 N1 C13 C12 -177.8(4) . . . . ?
C1 N1 C14 C15 97.0(5) . . . . ?
C1 C2 C3 C4 178.3(4) . . . . ?
C19 C18 C17 C16 -1.8(7) . . . . ?
C6 C7 C2 C1 -179.2(4) . . . . ?
C6 C7 C2 C3 0.8(6) . . . . ?
C6 C5 C4 C3 -1.1(8) . . . . ?
C16 C15 C20 C19 -1.3(7) . . . . ?
C16 C15 C14 N1 128.1(5) . . . . ?
C14 N1 C13 C8 -175.1(4) . . . . ?
C14 N1 C13 C12 3.6(6) . . . . ?
C14 N1 C1 O1 -1.8(6) . . . . ?
C14 N1 C1 C2 178.0(4) . . . . ?
C14 C15 C20 C19 179.6(4) . . . . ?
C14 C15 C16 C17 179.4(4) . . . . ?
C17 C18 C19 C20 0.9(7) . . . . ?
C3 C2 C1 O1 -1.8(7) . . . . ?
C3 C2 C1 N1 178.4(4) . . . . ?


_olex2_date_sample_data_collection 2021-01-26
_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 1.897
_oxdiff_exptl_absorpt_empirical_full_min 0.677
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_8778
_database_code_depnum_ccdc_archive 'CCDC 2342465'
loop_
_audit_author_name
_audit_author_address
'Yu Xiong'
;Shenzhen University
China
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2021-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Cl N O'
_chemical_formula_sum            'C20 H14 Cl N O'
_chemical_formula_weight         319.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.6526(8)
_cell_length_b                   25.098(3)
_cell_length_c                   11.1799(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.355(14)
_cell_angle_gamma                90
_cell_volume                     1555.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1954
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2450
_cell_measurement_theta_min      4.0150
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6284
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.718
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  82.10   0.90    5.00    --   15.65  57.00 120.00   89
  2  ω     36.00  63.00   0.90    5.00    --   15.65 178.00 -90.00   30
  3  ω    -42.00  40.80   0.90    5.00    --   15.65 -77.00 -30.00   92
  4  ω     -8.00  20.80   0.90    5.00    --  -16.43 -99.00 120.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0607141000
_diffrn_orient_matrix_UB_12      -0.0076832000
_diffrn_orient_matrix_UB_13      -0.0592342000
_diffrn_orient_matrix_UB_21      0.0283393000
_diffrn_orient_matrix_UB_22      -0.0270380000
_diffrn_orient_matrix_UB_23      0.0145567000
_diffrn_orient_matrix_UB_31      -0.1091606000
_diffrn_orient_matrix_UB_32      -0.0027709000
_diffrn_orient_matrix_UB_33      0.0216432000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2106
_reflns_number_total             2734
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.086
_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)+(0.0334P)²+0.4823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1058
_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:
 C16(H16), C17(H17), C20(H20), C12(H12), C19(H19), C3(H3), C9(H9), C6(H6),
 C4(H4), C5(H5), C11(H11), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.68322(14) 0.95719(3) 0.63664(7) 0.0778(3) Uani 1 1 d . . . . .
N1 N 0.2835(3) 0.70716(7) 0.48005(15) 0.0412(4) Uani 1 1 d . . . . .
O1 O 0.0394(3) 0.72462(7) 0.61415(15) 0.0614(5) Uani 1 1 d . . . . .
C15 C 0.3235(4) 0.80639(8) 0.47384(18) 0.0381(5) Uani 1 1 d . . . . .
C16 C 0.5591(4) 0.80575(9) 0.53896(19) 0.0422(5) Uani 1 1 d . . . . .
H16 H 0.644078 0.773817 0.549539 0.051 Uiso 1 1 calc R . . . .
C1 C 0.1785(4) 0.69367(9) 0.5771(2) 0.0430(5) Uani 1 1 d . . . . .
C8 C 0.5184(4) 0.62539(9) 0.49265(18) 0.0398(5) Uani 1 1 d . . . . .
C7 C 0.3969(4) 0.60696(8) 0.58876(18) 0.0392(5) Uani 1 1 d . . . . .
C2 C 0.2344(4) 0.64067(8) 0.63039(18) 0.0394(5) Uani 1 1 d . . . . .
C13 C 0.4587(4) 0.67578(9) 0.43977(18) 0.0402(5) Uani 1 1 d . . . . .
C18 C 0.5433(4) 0.89904(9) 0.5734(2) 0.0445(6) Uani 1 1 d . . . . .
C17 C 0.6688(4) 0.85218(9) 0.5883(2) 0.0447(5) Uani 1 1 d . . . . .
H17 H 0.827250 0.851512 0.631440 0.054 Uiso 1 1 calc R . . . .
C20 C 0.2013(4) 0.85459(9) 0.4595(2) 0.0458(6) Uani 1 1 d . . . . .
H20 H 0.043783 0.855717 0.415175 0.055 Uiso 1 1 calc R . . . .
C14 C 0.1952(4) 0.75694(9) 0.4178(2) 0.0495(6) Uani 1 1 d . . . . .
H14A H 0.024443 0.760447 0.418183 0.059 Uiso 1 1 calc R . . . .
H14B H 0.212709 0.754634 0.333337 0.059 Uiso 1 1 calc R . . . .
C12 C 0.5767(4) 0.69450(10) 0.3494(2) 0.0520(6) Uani 1 1 d . . . . .
H12 H 0.540109 0.728065 0.315585 0.062 Uiso 1 1 calc R . . . .
C19 C 0.3091(4) 0.90090(9) 0.5096(2) 0.0514(6) Uani 1 1 d . . . . .
H19 H 0.224598 0.932912 0.500458 0.062 Uiso 1 1 calc R . . . .
C3 C 0.1112(4) 0.62363(10) 0.72056(19) 0.0506(6) Uani 1 1 d . . . . .
H3 H 0.004566 0.646597 0.748228 0.061 Uiso 1 1 calc R . . . .
C9 C 0.6937(4) 0.59537(10) 0.4508(2) 0.0544(6) Uani 1 1 d . . . . .
H9 H 0.735270 0.562027 0.484797 0.065 Uiso 1 1 calc R . . . .
C6 C 0.4315(5) 0.55587(9) 0.6407(2) 0.0559(7) Uani 1 1 d . . . . .
H6 H 0.540297 0.532652 0.615561 0.067 Uiso 1 1 calc R . . . .
C4 C 0.1468(5) 0.57348(11) 0.7681(2) 0.0599(7) Uani 1 1 d . . . . .
H4 H 0.063482 0.562118 0.827367 0.072 Uiso 1 1 calc R . . . .
C5 C 0.3072(5) 0.53983(10) 0.7277(2) 0.0638(7) Uani 1 1 d . . . . .
H5 H 0.331235 0.505678 0.760137 0.077 Uiso 1 1 calc R . . . .
C11 C 0.7469(5) 0.66341(12) 0.3105(2) 0.0602(7) Uani 1 1 d . . . . .
H11 H 0.822950 0.675967 0.249514 0.072 Uiso 1 1 calc R . . . .
C10 C 0.8063(5) 0.61390(12) 0.3606(2) 0.0619(7) Uani 1 1 d . . . . .
H10 H 0.921692 0.593153 0.333679 0.074 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
Cl1 C18 1.742(2) . ?
N1 C1 1.378(3) . ?
N1 C13 1.407(3) . ?
N1 C14 1.469(3) . ?
O1 C1 1.233(2) . ?
C15 C16 1.386(3) . ?
C15 C20 1.387(3) . ?
C15 C14 1.510(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C1 C2 1.466(3) . ?
C8 C7 1.460(3) . ?
C8 C13 1.409(3) . ?
C8 C9 1.397(3) . ?
C7 C2 1.394(3) . ?
C7 C6 1.405(3) . ?
C2 C3 1.400(3) . ?
C13 C12 1.397(3) . ?
C18 C17 1.367(3) . ?
C18 C19 1.375(3) . ?
C17 H17 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.379(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C11 1.374(3) . ?
C19 H19 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.366(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.377(4) . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 123.65(18) . . ?
C1 N1 C14 115.06(18) . . ?
C13 N1 C14 121.27(17) . . ?
C16 C15 C20 118.4(2) . . ?
C16 C15 C14 122.79(19) . . ?
C20 C15 C14 118.8(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
N1 C1 C2 116.80(19) . . ?
O1 C1 N1 120.8(2) . . ?
O1 C1 C2 122.4(2) . . ?
C13 C8 C7 119.03(18) . . ?
C9 C8 C7 122.9(2) . . ?
C9 C8 C13 118.1(2) . . ?
C2 C7 C8 119.31(19) . . ?
C2 C7 C6 117.59(19) . . ?
C6 C7 C8 123.09(19) . . ?
C7 C2 C1 121.24(18) . . ?
C7 C2 C3 120.6(2) . . ?
C3 C2 C1 118.1(2) . . ?
N1 C13 C8 119.57(18) . . ?
C12 C13 N1 120.6(2) . . ?
C12 C13 C8 119.8(2) . . ?
C17 C18 Cl1 119.22(19) . . ?
C17 C18 C19 121.1(2) . . ?
C19 C18 Cl1 119.72(18) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.2 . . ?
C15 C20 H20 119.4 . . ?
C19 C20 C15 121.2(2) . . ?
C19 C20 H20 119.4 . . ?
N1 C14 C15 114.31(18) . . ?
N1 C14 H14A 108.7 . . ?
N1 C14 H14B 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 119.9 . . ?
C18 C19 C20 119.0(2) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.6(2) . . ?
C10 C9 H9 119.2 . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C12 C11 H11 119.6 . . ?
C12 C11 C10 120.9(2) . . ?
C10 C11 H11 119.6 . . ?
C9 C10 C11 119.5(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?


_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 1.271
_oxdiff_exptl_absorpt_empirical_full_min 0.611
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_8742
_database_code_depnum_ccdc_archive 'CCDC 2342464'
loop_
_audit_author_name
_audit_author_address
'Yu Xiong'
;Shenzhen University
China
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2020-12-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H13 Br Cl N O'
_chemical_formula_sum            'C20 H13 Br Cl N O'
_chemical_formula_weight         398.67
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.0938(7)
_cell_length_b                   21.7282(19)
_cell_length_c                   10.6282(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.716(9)
_cell_angle_gamma                90
_cell_volume                     1623.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1057
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.1710
_cell_measurement_theta_min      3.3830
_shelx_estimated_absorpt_T_max   0.642
_shelx_estimated_absorpt_T_min   0.451
_exptl_absorpt_coefficient_mu    2.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.631
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.1075
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6586
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.149
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  32.00   1.00    2.50    --   15.49 -57.00  60.00   35
  2  ω    -46.00  42.00   1.00    2.50    --   15.49 -77.00  30.00   88
  3  ω    -25.00  17.00   1.00    2.50    --  -16.12 -99.00-120.00   42
  4  ω     23.00  75.00   1.00    2.50    --   15.49  77.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0126759000
_diffrn_orient_matrix_UB_12      -0.0322820000
_diffrn_orient_matrix_UB_13      0.0054377000
_diffrn_orient_matrix_UB_21      -0.0312315000
_diffrn_orient_matrix_UB_22      0.0007244000
_diffrn_orient_matrix_UB_23      0.0606582000
_diffrn_orient_matrix_UB_31      -0.0952598000
_diffrn_orient_matrix_UB_32      -0.0045451000
_diffrn_orient_matrix_UB_33      -0.0286758000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1668
_reflns_number_total             2865
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      0.997
_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)+(0.0197P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0999
_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:
 C5(H5), C2(H2), C3(H3), C8(H8), C19(H19), C20(H20), C16(H16), C9(H9),
 C11(H11), C17(H17), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.10153(8) 0.80486(3) 0.56689(6) 0.0672(2) Uani 1 1 d . . . . .
Cl1 Cl 0.5907(2) 0.43457(7) 0.12764(10) 0.0647(5) Uani 1 1 d . . . . .
O1 O 0.9112(5) 0.60173(17) 0.7905(3) 0.0605(11) Uani 1 1 d . . . . .
N1 N 0.8182(5) 0.59025(19) 0.5787(3) 0.0365(10) Uani 1 1 d . . . . .
C7 C 0.7895(6) 0.4616(2) 0.6125(4) 0.0302(12) Uani 1 1 d . . . . .
C1 C 0.7585(6) 0.5530(2) 0.4727(4) 0.0335(12) Uani 1 1 d . . . . .
C6 C 0.7476(6) 0.4896(2) 0.4861(4) 0.0313(12) Uani 1 1 d . . . . .
C5 C 0.6959(6) 0.4532(2) 0.3778(4) 0.0350(12) Uani 1 1 d . . . . .
H5 H 0.6902 0.4106 0.3851 0.042 Uiso 1 1 calc R . . . .
C2 C 0.7105(6) 0.5797(2) 0.3518(4) 0.0398(13) Uani 1 1 d . . . . .
H2 H 0.7135 0.6223 0.3428 0.048 Uiso 1 1 calc R . . . .
C15 C 0.6638(6) 0.6937(2) 0.5630(4) 0.0375(12) Uani 1 1 d . . . . .
C3 C 0.6596(7) 0.5433(3) 0.2476(4) 0.0432(14) Uani 1 1 d . . . . .
H3 H 0.6290 0.5612 0.1680 0.052 Uiso 1 1 calc R . . . .
C13 C 0.8596(7) 0.5673(3) 0.7011(4) 0.0423(14) Uani 1 1 d . . . . .
C8 C 0.7772(6) 0.3987(3) 0.6357(4) 0.0400(14) Uani 1 1 d . . . . .
H8 H 0.7421 0.3719 0.5682 0.048 Uiso 1 1 calc R . . . .
C19 C 0.3892(7) 0.7205(2) 0.6623(4) 0.0422(14) Uani 1 1 d . . . . .
H19 H 0.3165 0.7157 0.7283 0.051 Uiso 1 1 calc R . . . .
C20 C 0.5559(7) 0.6873(2) 0.6620(4) 0.0410(13) Uani 1 1 d . . . . .
H20 H 0.5958 0.6605 0.7285 0.049 Uiso 1 1 calc R . . . .
C18 C 0.3323(7) 0.7601(2) 0.5656(5) 0.0413(13) Uani 1 1 d . . . . .
C12 C 0.8401(6) 0.5010(3) 0.7158(4) 0.0387(13) Uani 1 1 d . . . . .
C16 C 0.6042(7) 0.7350(3) 0.4690(5) 0.0492(15) Uani 1 1 d . . . . .
H16 H 0.6775 0.7405 0.4036 0.059 Uiso 1 1 calc R . . . .
C14 C 0.8453(7) 0.6565(2) 0.5645(4) 0.0448(14) Uani 1 1 d . . . . .
H14A H 0.8973 0.6639 0.4859 0.054 Uiso 1 1 calc R . . . .
H14B H 0.9378 0.6708 0.6338 0.054 Uiso 1 1 calc R . . . .
C9 C 0.8164(6) 0.3755(3) 0.7569(4) 0.0477(15) Uani 1 1 d . . . . .
H9 H 0.8096 0.3333 0.7702 0.057 Uiso 1 1 calc R . . . .
C11 C 0.8742(7) 0.4765(3) 0.8382(4) 0.0506(15) Uani 1 1 d . . . . .
H11 H 0.9033 0.5029 0.9069 0.061 Uiso 1 1 calc R . . . .
C4 C 0.6537(6) 0.4808(3) 0.2603(4) 0.0393(13) Uani 1 1 d . . . . .
C17 C 0.4382(7) 0.7692(2) 0.4673(4) 0.0480(15) Uani 1 1 d . . . . .
H17 H 0.4000 0.7971 0.4024 0.058 Uiso 1 1 calc R . . . .
C10 C 0.8657(7) 0.4142(3) 0.8593(4) 0.0560(17) Uani 1 1 d . . . . .
H10 H 0.8928 0.3984 0.9410 0.067 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
Br1 C18 1.906(5) . ?
Cl1 C4 1.740(5) . ?
O1 C13 1.225(5) . ?
N1 C1 1.406(5) . ?
N1 C13 1.387(5) . ?
N1 C14 1.463(6) . ?
C7 C6 1.469(6) . ?
C7 C8 1.394(6) . ?
C7 C12 1.401(6) . ?
C1 C6 1.386(6) . ?
C1 C2 1.410(6) . ?
C6 C5 1.405(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(6) . ?
C15 C20 1.389(6) . ?
C15 C16 1.368(6) . ?
C15 C14 1.518(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(7) . ?
C13 C12 1.458(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(6) . ?
C19 C18 1.360(6) . ?
C20 H20 0.9300 . ?
C18 C17 1.381(6) . ?
C12 C11 1.396(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.390(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C10 1.382(7) . ?
C11 H11 0.9300 . ?
C11 C10 1.375(7) . ?
C17 H17 0.9300 . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C14 120.9(4) . . ?
C13 N1 C1 123.2(5) . . ?
C13 N1 C14 115.8(4) . . ?
C8 C7 C6 124.0(4) . . ?
C8 C7 C12 118.5(4) . . ?
C12 C7 C6 117.5(5) . . ?
N1 C1 C2 120.2(5) . . ?
C6 C1 N1 120.3(4) . . ?
C6 C1 C2 119.5(4) . . ?
C1 C6 C7 119.9(4) . . ?
C1 C6 C5 119.2(4) . . ?
C5 C6 C7 120.9(5) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.8(5) . . ?
C4 C5 H5 120.1 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(5) . . ?
C3 C2 H2 119.8 . . ?
C20 C15 C14 119.4(4) . . ?
C16 C15 C20 118.1(5) . . ?
C16 C15 C14 122.4(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
O1 C13 N1 120.8(5) . . ?
O1 C13 C12 122.9(5) . . ?
N1 C13 C12 116.3(4) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.0(5) . . ?
C9 C8 H8 119.5 . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.6(4) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.5(5) . . ?
C19 C20 H20 119.8 . . ?
C19 C18 Br1 119.0(4) . . ?
C19 C18 C17 121.8(5) . . ?
C17 C18 Br1 119.2(4) . . ?
C7 C12 C13 122.6(4) . . ?
C11 C12 C7 119.4(5) . . ?
C11 C12 C13 118.0(5) . . ?
C15 C16 H16 118.7 . . ?
C15 C16 C17 122.6(5) . . ?
C17 C16 H16 118.7 . . ?
N1 C14 C15 113.7(4) . . ?
N1 C14 H14A 108.8 . . ?
N1 C14 H14B 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(5) . . ?
C10 C9 H9 119.6 . . ?
C12 C11 H11 119.3 . . ?
C10 C11 C12 121.4(5) . . ?
C10 C11 H11 119.3 . . ?
C5 C4 Cl1 118.9(4) . . ?
C3 C4 Cl1 120.1(4) . . ?
C3 C4 C5 121.0(5) . . ?
C18 C17 C16 117.4(5) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.9(5) . . ?
C11 C10 H10 120.6 . . ?


_olex2_date_sample_data_collection 2020-12-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.585
_oxdiff_exptl_absorpt_empirical_full_min 0.706
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_9030
_database_code_depnum_ccdc_archive 'CCDC 2342466'
loop_
_audit_author_name
_audit_author_address
'Yu Xiong'
;Shenzhen University
China
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2021-01-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Br N O'
_chemical_formula_sum            'C20 H14 Br N O'
_chemical_formula_weight         364.23
_chemical_absolute_configuration rmad
_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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.3495(8)
_cell_length_b                   5.1564(4)
_cell_length_c                   18.3745(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.763(8)
_cell_angle_gamma                90
_cell_volume                     771.54(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2051
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9900
_cell_measurement_theta_min      2.2680
_shelx_estimated_absorpt_T_max   0.740
_shelx_estimated_absorpt_T_min   0.555
_exptl_absorpt_coefficient_mu    2.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7948
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.347
_diffrn_reflns_theta_min         2.273
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  62.00   1.00    4.00    --   15.65  57.00  60.00   57
  2  ω      1.00  44.00   1.00    4.00    --  -16.43  57.00 -60.00   43
  3  ω     -1.00  72.00   1.00    4.00    --   15.65  57.00-150.00   73
  4  ω    -31.00  -2.00   1.00    4.00    --  -16.43  57.00 -60.00   29
  5  ω    -51.00  31.00   1.00    4.00    --   15.65 -57.00  90.00   82
  6  ω     -9.00  23.00   1.00    4.00    --  -16.43 -99.00-120.00   32
  7  ω    -32.00  32.00   1.00    4.00    --   15.65 -57.00-150.00   64
  8  ω    -83.00  -2.00   1.00    4.00    --  -16.43 -77.00 -30.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0626772000
_diffrn_orient_matrix_UB_12      -0.0620796000
_diffrn_orient_matrix_UB_13      0.0266612000
_diffrn_orient_matrix_UB_21      -0.0524435000
_diffrn_orient_matrix_UB_22      -0.0035774000
_diffrn_orient_matrix_UB_23      0.0255641000
_diffrn_orient_matrix_UB_31      -0.0301660000
_diffrn_orient_matrix_UB_32      -0.1226587000
_diffrn_orient_matrix_UB_33      -0.0142207000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.717
_reflns_number_gt                2253
_reflns_number_total             3448
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 681 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      0.976
_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)+(0.0206P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0730
_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:
 C19(H19), C9(H9), C6(H6), C12(H12), C17(H17), C16(H16), C11(H11), C3(H3),
 C10(H10), C5(H5), C4(H4), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.85135(6) 0.61313(16) 0.11625(3) 0.0665(2) Uani 1 1 d . . . . .
O1 O 0.8861(4) 0.9900(7) -0.28136(19) 0.0613(11) Uani 1 1 d . . . . .
C19 C 0.8344(5) 0.6126(14) -0.0397(2) 0.0457(11) Uani 1 1 d . . . . .
H19 H 0.901942 0.467712 -0.029362 0.055 Uiso 1 1 calc R U . . .
C18 C 0.7782(6) 0.7357(9) 0.0163(3) 0.0423(13) Uani 1 1 d . . . . .
C2 C 0.7522(6) 0.6625(10) -0.3632(2) 0.0403(13) Uani 1 1 d . . . . .
C7 C 0.6201(6) 0.4926(9) -0.3820(2) 0.0392(12) Uani 1 1 d . . . . .
C1 C 0.7670(7) 0.8492(10) -0.3015(3) 0.0433(13) Uani 1 1 d . . . . .
C13 C 0.5014(6) 0.6873(8) -0.2835(3) 0.0405(14) Uani 1 1 d . . . . .
N1 N 0.6374(5) 0.8535(7) -0.2658(2) 0.0399(10) Uani 1 1 d . . . . .
C9 C 0.3549(7) 0.3348(10) -0.3535(3) 0.0555(15) Uani 1 1 d . . . . .
H9 H 0.346938 0.208713 -0.390336 0.067 Uiso 1 1 calc R U . . .
C6 C 0.6178(7) 0.3171(10) -0.4402(3) 0.0559(15) Uani 1 1 d . . . . .
H6 H 0.532164 0.198693 -0.452813 0.067 Uiso 1 1 calc R U . . .
C12 C 0.3746(7) 0.7043(9) -0.2442(3) 0.0549(16) Uani 1 1 d . . . . .
H12 H 0.380268 0.827954 -0.206841 0.066 Uiso 1 1 calc R U . . .
C14 C 0.6492(7) 1.0429(8) -0.2045(2) 0.0498(15) Uani 1 1 d . . . . .
H14A H 0.545586 1.134658 -0.210934 0.060 Uiso 1 1 calc R U . . .
H14B H 0.733315 1.169213 -0.207911 0.060 Uiso 1 1 calc R U . . .
C17 C 0.6765(6) 0.9456(10) 0.0022(3) 0.0472(13) Uani 1 1 d . . . . .
H17 H 0.638197 1.025542 0.040462 0.057 Uiso 1 1 calc R U . . .
C16 C 0.6319(6) 1.0367(9) -0.0702(3) 0.0454(14) Uani 1 1 d . . . . .
H16 H 0.561590 1.178324 -0.080742 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2427(7) 0.5387(12) -0.2609(3) 0.065(2) Uani 1 1 d . . . . .
H11 H 0.158591 0.553275 -0.235381 0.078 Uiso 1 1 calc R U . . .
C3 C 0.8761(6) 0.6631(13) -0.4036(3) 0.0531(17) Uani 1 1 d . . . . .
H3 H 0.962758 0.779913 -0.391233 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2336(7) 0.3520(12) -0.3148(3) 0.0645(17) Uani 1 1 d . . . . .
H10 H 0.145145 0.237945 -0.324963 0.077 Uiso 1 1 calc R U . . .
C5 C 0.7408(8) 0.3180(11) -0.4786(3) 0.0621(16) Uani 1 1 d . . . . .
H5 H 0.737527 0.199721 -0.517125 0.075 Uiso 1 1 calc R U . . .
C4 C 0.8705(7) 0.4928(11) -0.4611(3) 0.0607(16) Uani 1 1 d . . . . .
H4 H 0.952316 0.493851 -0.488239 0.073 Uiso 1 1 calc R U . . .
C20 C 0.7888(6) 0.7078(9) -0.1112(3) 0.0457(14) Uani 1 1 d . . . . .
H20 H 0.826060 0.625628 -0.149333 0.055 Uiso 1 1 calc R U . . .
C8 C 0.4917(6) 0.5011(9) -0.3397(3) 0.0407(13) Uani 1 1 d . . . . .
C15 C 0.6895(6) 0.9215(9) -0.1274(2) 0.0383(12) 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
Br1 C18 1.910(4) . ?
O1 C1 1.221(6) . ?
C19 H19 0.9300 . ?
C19 C18 1.377(6) . ?
C19 C20 1.375(6) . ?
C18 C17 1.364(6) . ?
C2 C7 1.391(6) . ?
C2 C1 1.472(6) . ?
C2 C3 1.401(6) . ?
C7 C6 1.397(6) . ?
C7 C8 1.458(7) . ?
C1 N1 1.384(6) . ?
C13 N1 1.402(6) . ?
C13 C12 1.410(7) . ?
C13 C8 1.399(6) . ?
N1 C14 1.477(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(7) . ?
C9 C8 1.406(7) . ?
C6 H6 0.9300 . ?
C6 C5 1.369(8) . ?
C12 H12 0.9300 . ?
C12 C11 1.374(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.518(6) . ?
C17 H17 0.9300 . ?
C17 C16 1.384(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.381(6) . ?
C11 H11 0.9300 . ?
C11 C10 1.371(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(7) . ?
C10 H10 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.391(8) . ?
C4 H4 0.9300 . ?
C20 H20 0.9300 . ?
C20 C15 1.372(6) . ?

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
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C20 C19 C18 118.7(5) . . ?
C19 C18 Br1 118.5(4) . . ?
C17 C18 Br1 119.9(4) . . ?
C17 C18 C19 121.7(5) . . ?
C7 C2 C1 122.0(5) . . ?
C7 C2 C3 120.5(5) . . ?
C3 C2 C1 117.5(5) . . ?
C2 C7 C6 118.3(5) . . ?
C2 C7 C8 119.0(4) . . ?
C6 C7 C8 122.7(5) . . ?
O1 C1 C2 123.1(5) . . ?
O1 C1 N1 121.2(5) . . ?
N1 C1 C2 115.7(5) . . ?
N1 C13 C12 120.3(4) . . ?
C8 C13 N1 120.2(4) . . ?
C8 C13 C12 119.5(5) . . ?
C1 N1 C13 124.0(4) . . ?
C1 N1 C14 116.3(4) . . ?
C13 N1 C14 119.7(4) . . ?
C10 C9 H9 118.9 . . ?
C10 C9 C8 122.3(6) . . ?
C8 C9 H9 118.9 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.5(5) . . ?
C5 C6 H6 119.8 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.1(5) . . ?
C11 C12 H12 119.9 . . ?
N1 C14 H14A 108.8 . . ?
N1 C14 H14B 108.8 . . ?
N1 C14 C15 113.8(4) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C18 C17 H17 120.8 . . ?
C18 C17 C16 118.4(4) . . ?
C16 C17 H17 120.8 . . ?
C17 C16 H16 119.3 . . ?
C15 C16 C17 121.4(4) . . ?
C15 C16 H16 119.3 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.8(5) . . ?
C10 C11 H11 119.6 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C9 C10 C11 119.6(5) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C6 C5 H5 119.4 . . ?
C6 C5 C4 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C19 C20 H20 119.3 . . ?
C15 C20 C19 121.4(5) . . ?
C15 C20 H20 119.3 . . ?
C13 C8 C7 119.0(4) . . ?
C13 C8 C9 117.7(5) . . ?
C9 C8 C7 123.3(5) . . ?
C16 C15 C14 119.3(4) . . ?
C20 C15 C14 122.2(4) . . ?
C20 C15 C16 118.4(4) . . ?

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 C18 C17 C16 177.1(3) . . . . ?
O1 C1 N1 C13 -176.4(4) . . . . ?
O1 C1 N1 C14 2.1(7) . . . . ?
C19 C18 C17 C16 -0.9(7) . . . . ?
C19 C20 C15 C14 174.9(4) . . . . ?
C19 C20 C15 C16 -1.7(7) . . . . ?
C18 C19 C20 C15 0.1(7) . . . . ?
C18 C17 C16 C15 -0.8(7) . . . . ?
C2 C7 C6 C5 -1.7(7) . . . . ?
C2 C7 C8 C13 2.7(6) . . . . ?
C2 C7 C8 C9 -178.9(4) . . . . ?
C2 C1 N1 C13 2.5(6) . . . . ?
C2 C1 N1 C14 -179.0(4) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C7 C2 C1 O1 175.8(4) . . . . ?
C7 C2 C1 N1 -3.0(6) . . . . ?
C7 C2 C3 C4 -1.3(8) . . . . ?
C7 C6 C5 C4 -0.1(8) . . . . ?
C1 C2 C7 C6 -178.3(4) . . . . ?
C1 C2 C7 C8 0.5(6) . . . . ?
C1 C2 C3 C4 179.4(4) . . . . ?
C1 N1 C14 C15 -105.7(5) . . . . ?
C13 N1 C14 C15 72.9(5) . . . . ?
C13 C12 C11 C10 1.2(7) . . . . ?
N1 C13 C12 C11 -179.1(4) . . . . ?
N1 C13 C8 C7 -3.3(6) . . . . ?
N1 C13 C8 C9 178.2(4) . . . . ?
N1 C14 C15 C16 -149.8(5) . . . . ?
N1 C14 C15 C20 33.6(7) . . . . ?
C6 C7 C8 C13 -178.5(4) . . . . ?
C6 C7 C8 C9 -0.1(7) . . . . ?
C6 C5 C4 C3 1.2(8) . . . . ?
C12 C13 N1 C1 179.9(4) . . . . ?
C12 C13 N1 C14 1.4(6) . . . . ?
C12 C13 C8 C7 177.4(4) . . . . ?
C12 C13 C8 C9 -1.0(6) . . . . ?
C12 C11 C10 C9 -1.6(8) . . . . ?
C17 C16 C15 C14 -174.6(4) . . . . ?
C17 C16 C15 C20 2.1(7) . . . . ?
C3 C2 C7 C6 2.4(7) . . . . ?
C3 C2 C7 C8 -178.8(4) . . . . ?
C3 C2 C1 O1 -4.9(7) . . . . ?
C3 C2 C1 N1 176.3(4) . . . . ?
C10 C9 C8 C7 -177.8(5) . . . . ?
C10 C9 C8 C13 0.7(7) . . . . ?
C20 C19 C18 Br1 -176.8(4) . . . . ?
C20 C19 C18 C17 1.2(7) . . . . ?
C8 C7 C6 C5 179.5(5) . . . . ?
C8 C13 N1 C1 0.6(6) . . . . ?
C8 C13 N1 C14 -177.8(4) . . . . ?
C8 C13 C12 C11 0.2(7) . . . . ?
C8 C9 C10 C11 0.7(8) . . . . ?


_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 1.960
_oxdiff_exptl_absorpt_empirical_full_min 0.580
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_9386
_database_code_depnum_ccdc_archive 'CCDC 2342468'
loop_
_audit_author_name
_audit_author_address
'Yu Xiong'
;Shenzhen University
China
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2021-04-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 N2 O'
_chemical_formula_sum            'C21 H14 N2 O'
_chemical_formula_weight         310.34
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   18.334(4)
_cell_length_b                   5.0895(10)
_cell_length_c                   18.931(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.16(3)
_cell_angle_gamma                90
_cell_volume                     1571.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.5780
_cell_measurement_theta_min      3.6030
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_unetI/netI     0.1725
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11054
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        24.499
_diffrn_reflns_theta_max         24.499
_diffrn_reflns_theta_min         2.097
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.975
_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     -1.00  83.00   1.00   10.00    --   15.65  57.00  90.00   84
  2  ω     19.00  68.00   1.00   10.00    --   15.65  57.00 150.00   49
  3  ω     53.00  86.00   1.00   10.00    --   15.65 178.00  30.00   33
  4  ω    -33.00  48.00   1.00   10.00    --  -16.59  57.00-150.00   81
  5  ω    -32.00  -6.00   1.00   10.00    --   15.65 -57.00 -90.00   26
  6  ω    -24.00  20.00   1.00   10.00    --  -16.59 -99.00-120.00   44
  7  ω    -52.00  42.00   1.00   10.00    --   15.65 -77.00 -30.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0345505000
_diffrn_orient_matrix_UB_12      0.0003118000
_diffrn_orient_matrix_UB_13      0.0074518000
_diffrn_orient_matrix_UB_21      -0.0263300000
_diffrn_orient_matrix_UB_22      -0.0073462000
_diffrn_orient_matrix_UB_23      -0.0414115000
_diffrn_orient_matrix_UB_31      0.0013269000
_diffrn_orient_matrix_UB_32      -0.1391679000
_diffrn_orient_matrix_UB_33      0.0021798000
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Advanced Light Source, station 11.3.1'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.854
_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                2316
_reflns_number_total             4800
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 527 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -7.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         4800
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      0.836
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0793
_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:
 C35(H35a,H35b), C14(H14a,H14b)
2.b Aromatic/amide H refined with riding coordinates:
 C41(H41), C27(H27), C33(H33), C16(H16), C19(H19), C20(H20), C24(H24),
 C26(H26), C9(H9), C17(H17), C30(H30), C38(H38), C25(H25), C32(H32), C6(H6),
 C4(H4), C12(H12), C3(H3), C5(H5), C37(H37), C40(H40), C31(H31), C11(H11),
 C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7292(2) 0.5332(10) 0.3317(3) 0.0734(15) Uani 1 1 d . . . . .
N3 N 0.3274(3) -0.3687(9) 0.0784(3) 0.0460(13) Uani 1 1 d . . . . .
N1 N 0.7635(3) 0.3671(10) 0.4535(3) 0.0477(13) Uani 1 1 d . . . . .
O2 O 0.4160(3) -0.5258(10) 0.1971(3) 0.0868(17) Uani 1 1 d . . . . .
C13 C 0.8063(4) 0.1890(13) 0.5149(4) 0.0467(17) Uani 1 1 d . . . . .
C34 C 0.3071(4) -0.1909(12) 0.0146(3) 0.0423(15) Uani 1 1 d . . . . .
C29 C 0.3646(4) -0.0163(12) 0.0143(3) 0.0380(15) Uani 1 1 d . . . . .
C15 C 0.6198(3) 0.4551(12) 0.4304(3) 0.0428(16) Uani 1 1 d . . . . .
C22 C 0.4039(4) -0.3766(13) 0.1418(4) 0.0519(18) Uani 1 1 d . . . . .
C8 C 0.8616(3) 0.0139(12) 0.5082(3) 0.0422(16) Uani 1 1 d . . . . .
C2 C 0.8275(3) 0.1913(12) 0.3768(4) 0.0417(16) Uani 1 1 d . . . . .
C23 C 0.4661(4) -0.2006(12) 0.1405(3) 0.0394(15) Uani 1 1 d . . . . .
C7 C 0.8726(3) 0.0164(12) 0.4365(3) 0.0412(15) Uani 1 1 d . . . . .
C28 C 0.4483(4) -0.0148(13) 0.0805(3) 0.0444(16) Uani 1 1 d . . . . .
C1 C 0.7702(4) 0.3752(13) 0.3837(4) 0.0514(18) Uani 1 1 d . . . . .
C41 C 0.2202(4) -0.2437(13) 0.1515(3) 0.0589(19) Uani 1 1 d . . . . .
H41 H 0.2729 -0.1741 0.1766 0.071 Uiso 1 1 calc R U . . .
C27 C 0.5098(4) 0.1528(13) 0.0859(4) 0.0555(18) Uani 1 1 d . . . . .
H27 H 0.4988 0.2784 0.0467 0.067 Uiso 1 1 calc R U . . .
C33 C 0.2265(4) -0.1865(13) -0.0481(4) 0.0547(18) Uani 1 1 d . . . . .
H33 H 0.1873 -0.3014 -0.0478 0.066 Uiso 1 1 calc R U . . .
C16 C 0.5679(4) 0.5875(12) 0.4524(3) 0.0531(18) Uani 1 1 d . . . . .
H16 H 0.5882 0.7275 0.4877 0.064 Uiso 1 1 calc R U . . .
C36 C 0.2028(4) -0.4402(13) 0.0970(3) 0.0487(18) Uani 1 1 d . . . . .
C19 C 0.5087(4) 0.1694(12) 0.3505(3) 0.0522(18) Uani 1 1 d . . . . .
H19 H 0.4891 0.0265 0.3163 0.063 Uiso 1 1 calc R U . . .
C20 C 0.5902(3) 0.2479(12) 0.3800(3) 0.0484(17) Uani 1 1 d . . . . .
H20 H 0.6249 0.1568 0.3650 0.058 Uiso 1 1 calc R U . . .
C24 C 0.5460(4) -0.2166(13) 0.2039(3) 0.0547(18) Uani 1 1 d . . . . .
H24 H 0.5583 -0.3411 0.2437 0.066 Uiso 1 1 calc R U . . .
C18 C 0.4573(4) 0.3073(14) 0.3728(3) 0.0486(17) Uani 1 1 d . . . . .
C35 C 0.2656(4) -0.5542(11) 0.0754(3) 0.0576(18) Uani 1 1 d . . . . .
H35A H 0.2930 -0.6987 0.1111 0.069 Uiso 1 1 calc R U . . .
H35B H 0.2375 -0.6258 0.0221 0.069 Uiso 1 1 calc R U . . .
C39 C 0.0838(4) -0.2513(14) 0.1341(4) 0.0559(19) Uani 1 1 d . . . . .
C26 C 0.5866(4) 0.1363(14) 0.1482(4) 0.062(2) Uani 1 1 d . . . . .
H26 H 0.6269 0.2527 0.1508 0.075 Uiso 1 1 calc R U . . .
C9 C 0.9045(4) -0.1594(14) 0.5715(4) 0.064(2) Uani 1 1 d . . . . .
H9 H 0.9424 -0.2747 0.5687 0.077 Uiso 1 1 calc R U . . .
C17 C 0.4878(4) 0.5186(13) 0.4238(3) 0.0536(18) Uani 1 1 d . . . . .
H17 H 0.4535 0.6135 0.4386 0.064 Uiso 1 1 calc R U . . .
C30 C 0.3422(4) 0.1574(12) -0.0501(3) 0.0528(18) Uani 1 1 d . . . . .
H30 H 0.3812 0.2726 -0.0510 0.063 Uiso 1 1 calc R U . . .
C38 C 0.0648(4) -0.4552(14) 0.0809(4) 0.069(2) Uani 1 1 d . . . . .
H38 H 0.0129 -0.5305 0.0582 0.083 Uiso 1 1 calc R U . . .
C25 C 0.6056(4) -0.0472(15) 0.2067(4) 0.062(2) Uani 1 1 d . . . . .
H25 H 0.6586 -0.0574 0.2480 0.074 Uiso 1 1 calc R U . . .
C32 C 0.2059(4) -0.0100(16) -0.1105(4) 0.066(2) Uani 1 1 d . . . . .
H32 H 0.1526 -0.0071 -0.1514 0.079 Uiso 1 1 calc R U . . .
C6 C 0.9236(3) -0.1592(12) 0.4228(4) 0.0561(18) Uani 1 1 d . . . . .
H6 H 0.9536 -0.2832 0.4612 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8861(5) 0.0304(17) 0.2946(4) 0.072(2) Uani 1 1 d . . . . .
H4 H 0.8908 0.0349 0.2477 0.086 Uiso 1 1 calc R U . . .
C12 C 0.7930(4) 0.1787(13) 0.5813(4) 0.065(2) Uani 1 1 d . . . . .
H12 H 0.7548 0.2913 0.5848 0.078 Uiso 1 1 calc R U . . .
C3 C 0.8355(4) 0.2029(14) 0.3070(4) 0.060(2) Uani 1 1 d . . . . .
H3 H 0.8064 0.3283 0.2687 0.072 Uiso 1 1 calc R U . . .
C5 C 0.9299(4) -0.1503(16) 0.3535(5) 0.073(2) Uani 1 1 d . . . . .
H5 H 0.9644 -0.2683 0.3458 0.088 Uiso 1 1 calc R U . . .
C37 C 0.1258(4) -0.5466(13) 0.0619(4) 0.062(2) Uani 1 1 d . . . . .
H37 H 0.1138 -0.6811 0.0250 0.074 Uiso 1 1 calc R U . . .
C14 C 0.7064(3) 0.5585(11) 0.4599(4) 0.062(2) Uani 1 1 d . . . . .
H14A H 0.7048 0.7142 0.4296 0.075 Uiso 1 1 calc R U . . .
H14B H 0.7272 0.6104 0.5150 0.075 Uiso 1 1 calc R U . . .
C40 C 0.1604(4) -0.1474(13) 0.1698(3) 0.063(2) Uani 1 1 d . . . . .
H40 H 0.1726 -0.0118 0.2064 0.076 Uiso 1 1 calc R U . . .
C31 C 0.2632(4) 0.1601(14) -0.1124(4) 0.066(2) Uani 1 1 d . . . . .
H31 H 0.2493 0.2754 -0.1547 0.080 Uiso 1 1 calc R U . . .
C21 C 0.3729(4) 0.2219(16) 0.3423(4) 0.074(2) Uani 1 1 d . . . . .
C42 C 0.0205(4) -0.1430(16) 0.1523(4) 0.075(2) Uani 1 1 d . . . . .
C11 C 0.8354(5) 0.0043(18) 0.6426(4) 0.076(2) Uani 1 1 d . . . . .
H11 H 0.8262 -0.0005 0.6870 0.091 Uiso 1 1 calc R U . . .
N2 N 0.3066(4) 0.1601(16) 0.3208(4) 0.120(3) Uani 1 1 d . . . . .
C10 C 0.8914(5) -0.1617(16) 0.6366(4) 0.081(2) Uani 1 1 d . . . . .
H10 H 0.9210 -0.2776 0.6778 0.098 Uiso 1 1 calc R U . . .
N4 N -0.0300(4) -0.0478(16) 0.1632(4) 0.119(3) 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
O1 C1 1.227(6) . ?
N3 C34 1.416(6) . ?
N3 C22 1.369(7) . ?
N3 C35 1.456(6) . ?
N1 C13 1.399(7) . ?
N1 C1 1.383(6) . ?
N1 C14 1.475(6) . ?
O2 C22 1.230(6) . ?
C13 C8 1.398(7) . ?
C13 C12 1.387(7) . ?
C34 C29 1.380(7) . ?
C34 C33 1.412(7) . ?
C29 C28 1.473(7) . ?
C29 C30 1.407(7) . ?
C15 C16 1.377(7) . ?
C15 C20 1.358(7) . ?
C15 C14 1.517(7) . ?
C22 C23 1.459(7) . ?
C8 C7 1.461(7) . ?
C8 C9 1.404(7) . ?
C2 C7 1.379(7) . ?
C2 C1 1.456(7) . ?
C2 C3 1.396(7) . ?
C23 C28 1.398(7) . ?
C23 C24 1.410(7) . ?
C7 C6 1.401(7) . ?
C28 C27 1.380(7) . ?
C41 H41 0.9300 . ?
C41 C36 1.366(7) . ?
C41 C40 1.382(7) . ?
C27 H27 0.9300 . ?
C27 C26 1.365(7) . ?
C33 H33 0.9300 . ?
C33 C32 1.391(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.360(7) . ?
C36 C35 1.504(7) . ?
C36 C37 1.367(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.393(7) . ?
C19 C18 1.387(7) . ?
C20 H20 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.375(8) . ?
C18 C17 1.382(8) . ?
C18 C21 1.449(8) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C39 C38 1.376(8) . ?
C39 C40 1.358(8) . ?
C39 C42 1.460(8) . ?
C26 H26 0.9300 . ?
C26 C25 1.367(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.359(7) . ?
C17 H17 0.9300 . ?
C30 H30 0.9300 . ?
C30 C31 1.389(7) . ?
C38 H38 0.9300 . ?
C38 C37 1.401(7) . ?
C25 H25 0.9300 . ?
C32 H32 0.9300 . ?
C32 C31 1.374(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.369(7) . ?
C4 H4 0.9300 . ?
C4 C3 1.372(8) . ?
C4 C5 1.385(9) . ?
C12 H12 0.9300 . ?
C12 C11 1.384(8) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C37 H37 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C40 H40 0.9300 . ?
C31 H31 0.9300 . ?
C21 N2 1.137(7) . ?
C42 N4 1.144(7) . ?
C11 H11 0.9300 . ?
C11 C10 1.374(9) . ?
C10 H10 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
C34 N3 C35 119.0(5) . . ?
C22 N3 C34 122.1(5) . . ?
C22 N3 C35 118.9(5) . . ?
C13 N1 C14 120.7(5) . . ?
C1 N1 C13 123.5(5) . . ?
C1 N1 C14 115.8(5) . . ?
C8 C13 N1 119.5(6) . . ?
C12 C13 N1 121.0(7) . . ?
C12 C13 C8 119.5(6) . . ?
C29 C34 N3 120.7(5) . . ?
C29 C34 C33 119.6(6) . . ?
C33 C34 N3 119.6(6) . . ?
C34 C29 C28 120.1(5) . . ?
C34 C29 C30 119.2(6) . . ?
C30 C29 C28 120.7(6) . . ?
C16 C15 C14 118.1(6) . . ?
C20 C15 C16 118.9(5) . . ?
C20 C15 C14 122.9(5) . . ?
N3 C22 C23 117.6(6) . . ?
O2 C22 N3 118.6(6) . . ?
O2 C22 C23 123.8(6) . . ?
C13 C8 C7 119.5(6) . . ?
C13 C8 C9 118.1(6) . . ?
C9 C8 C7 122.5(6) . . ?
C7 C2 C1 121.9(6) . . ?
C7 C2 C3 121.3(6) . . ?
C3 C2 C1 116.7(6) . . ?
C28 C23 C22 122.3(6) . . ?
C28 C23 C24 119.8(6) . . ?
C24 C23 C22 117.8(6) . . ?
C2 C7 C8 118.8(6) . . ?
C2 C7 C6 117.4(6) . . ?
C6 C7 C8 123.7(6) . . ?
C23 C28 C29 117.0(6) . . ?
C27 C28 C29 124.5(6) . . ?
C27 C28 C23 118.6(6) . . ?
O1 C1 N1 119.8(6) . . ?
O1 C1 C2 123.5(6) . . ?
N1 C1 C2 116.7(6) . . ?
C36 C41 H41 119.7 . . ?
C36 C41 C40 120.6(6) . . ?
C40 C41 H41 119.7 . . ?
C28 C27 H27 119.6 . . ?
C26 C27 C28 120.8(6) . . ?
C26 C27 H27 119.6 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 C34 119.9(6) . . ?
C32 C33 H33 120.0 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(6) . . ?
C17 C16 H16 119.2 . . ?
C41 C36 C35 122.9(6) . . ?
C41 C36 C37 119.4(6) . . ?
C37 C36 C35 117.6(6) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.1(6) . . ?
C15 C20 C19 121.1(6) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.7(6) . . ?
C25 C24 H24 120.2 . . ?
C19 C18 C21 118.5(6) . . ?
C17 C18 C19 119.5(6) . . ?
C17 C18 C21 122.0(6) . . ?
N3 C35 C36 114.7(5) . . ?
N3 C35 H35A 108.6 . . ?
N3 C35 H35B 108.6 . . ?
C36 C35 H35A 108.6 . . ?
C36 C35 H35B 108.6 . . ?
H35A C35 H35B 107.6 . . ?
C38 C39 C42 119.7(7) . . ?
C40 C39 C38 121.1(6) . . ?
C40 C39 C42 119.2(7) . . ?
C27 C26 H26 119.2 . . ?
C27 C26 C25 121.5(7) . . ?
C25 C26 H26 119.2 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(7) . . ?
C10 C9 H9 119.4 . . ?
C16 C17 C18 119.9(6) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C29 C30 H30 119.3 . . ?
C31 C30 C29 121.3(6) . . ?
C31 C30 H30 119.3 . . ?
C39 C38 H38 120.9 . . ?
C39 C38 C37 118.3(6) . . ?
C37 C38 H38 120.9 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.6(6) . . ?
C26 C25 H25 120.2 . . ?
C33 C32 H32 119.5 . . ?
C31 C32 C33 120.9(7) . . ?
C31 C32 H32 119.5 . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.9(6) . . ?
C5 C6 H6 119.6 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(7) . . ?
C5 C4 H4 120.8 . . ?
C13 C12 H12 119.3 . . ?
C11 C12 C13 121.4(7) . . ?
C11 C12 H12 119.3 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(7) . . ?
C4 C3 H3 119.8 . . ?
C6 C5 C4 121.4(7) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C36 C37 C38 120.7(6) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
N1 C14 C15 113.8(5) . . ?
N1 C14 H14A 108.8 . . ?
N1 C14 H14B 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C41 C40 H40 120.1 . . ?
C39 C40 C41 119.8(6) . . ?
C39 C40 H40 120.1 . . ?
C30 C31 H31 120.5 . . ?
C32 C31 C30 119.0(7) . . ?
C32 C31 H31 120.5 . . ?
N2 C21 C18 177.3(8) . . ?
N4 C42 C39 176.1(9) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 C12 118.7(7) . . ?
C10 C11 H11 120.7 . . ?
C9 C10 C11 121.2(7) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?

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
N3 C34 C29 C28 0.6(8) . . . . ?
N3 C34 C29 C30 180.0(5) . . . . ?
N3 C34 C33 C32 179.2(5) . . . . ?
N3 C22 C23 C28 4.9(8) . . . . ?
N3 C22 C23 C24 -177.1(5) . . . . ?
N1 C13 C8 C7 -1.2(8) . . . . ?
N1 C13 C8 C9 179.0(5) . . . . ?
N1 C13 C12 C11 -179.6(6) . . . . ?
O2 C22 C23 C28 -173.4(6) . . . . ?
O2 C22 C23 C24 4.6(9) . . . . ?
C13 N1 C1 O1 178.3(5) . . . . ?
C13 N1 C1 C2 -2.0(8) . . . . ?
C13 N1 C14 C15 -87.9(6) . . . . ?
C13 C8 C7 C2 -0.4(8) . . . . ?
C13 C8 C7 C6 -176.9(6) . . . . ?
C13 C8 C9 C10 1.5(10) . . . . ?
C13 C12 C11 C10 -0.2(11) . . . . ?
C34 N3 C22 O2 176.1(5) . . . . ?
C34 N3 C22 C23 -2.3(8) . . . . ?
C34 N3 C35 C36 -79.0(6) . . . . ?
C34 C29 C28 C23 1.8(8) . . . . ?
C34 C29 C28 C27 -179.6(6) . . . . ?
C34 C29 C30 C31 1.4(9) . . . . ?
C34 C33 C32 C31 0.5(10) . . . . ?
C29 C34 C33 C32 1.2(9) . . . . ?
C29 C28 C27 C26 -178.1(5) . . . . ?
C29 C30 C31 C32 0.2(10) . . . . ?
C15 C16 C17 C18 1.5(9) . . . . ?
C22 N3 C34 C29 -0.3(8) . . . . ?
C22 N3 C34 C33 -178.2(5) . . . . ?
C22 N3 C35 C36 102.8(6) . . . . ?
C22 C23 C28 C29 -4.5(8) . . . . ?
C22 C23 C28 C27 176.8(5) . . . . ?
C22 C23 C24 C25 -177.4(5) . . . . ?
C8 C13 C12 C11 2.2(9) . . . . ?
C8 C7 C6 C5 178.6(6) . . . . ?
C8 C9 C10 C11 0.5(12) . . . . ?
C2 C7 C6 C5 2.0(8) . . . . ?
C23 C28 C27 C26 0.5(9) . . . . ?
C23 C24 C25 C26 0.5(9) . . . . ?
C7 C8 C9 C10 -178.3(6) . . . . ?
C7 C2 C1 O1 180.0(6) . . . . ?
C7 C2 C1 N1 0.3(8) . . . . ?
C7 C2 C3 C4 3.1(9) . . . . ?
C7 C6 C5 C4 -0.3(10) . . . . ?
C28 C29 C30 C31 -179.2(5) . . . . ?
C28 C23 C24 C25 0.7(9) . . . . ?
C28 C27 C26 C25 0.7(10) . . . . ?
C1 N1 C13 C8 2.5(8) . . . . ?
C1 N1 C13 C12 -175.8(5) . . . . ?
C1 N1 C14 C15 91.3(6) . . . . ?
C1 C2 C7 C8 0.8(8) . . . . ?
C1 C2 C7 C6 177.6(5) . . . . ?
C1 C2 C3 C4 -177.8(6) . . . . ?
C41 C36 C35 N3 -32.7(8) . . . . ?
C41 C36 C37 C38 0.4(10) . . . . ?
C27 C26 C25 C24 -1.3(10) . . . . ?
C33 C34 C29 C28 178.5(5) . . . . ?
C33 C34 C29 C30 -2.1(8) . . . . ?
C33 C32 C31 C30 -1.2(10) . . . . ?
C16 C15 C20 C19 0.2(9) . . . . ?
C16 C15 C14 N1 163.2(5) . . . . ?
C36 C41 C40 C39 0.9(9) . . . . ?
C19 C18 C17 C16 -0.8(9) . . . . ?
C20 C15 C16 C17 -1.2(9) . . . . ?
C20 C15 C14 N1 -20.6(8) . . . . ?
C20 C19 C18 C17 -0.2(9) . . . . ?
C20 C19 C18 C21 -179.4(6) . . . . ?
C24 C23 C28 C29 177.5(5) . . . . ?
C24 C23 C28 C27 -1.2(8) . . . . ?
C18 C19 C20 C15 0.4(9) . . . . ?
C35 N3 C34 C29 -178.5(5) . . . . ?
C35 N3 C34 C33 3.6(8) . . . . ?
C35 N3 C22 O2 -5.7(8) . . . . ?
C35 N3 C22 C23 175.9(5) . . . . ?
C35 C36 C37 C38 178.2(5) . . . . ?
C39 C38 C37 C36 1.7(10) . . . . ?
C9 C8 C7 C2 179.4(6) . . . . ?
C9 C8 C7 C6 2.8(9) . . . . ?
C30 C29 C28 C23 -177.6(5) . . . . ?
C30 C29 C28 C27 1.0(9) . . . . ?
C38 C39 C40 C41 1.3(10) . . . . ?
C12 C13 C8 C7 177.1(5) . . . . ?
C12 C13 C8 C9 -2.7(9) . . . . ?
C12 C11 C10 C9 -1.1(12) . . . . ?
C3 C2 C7 C8 179.9(5) . . . . ?
C3 C2 C7 C6 -3.4(8) . . . . ?
C3 C2 C1 O1 0.9(9) . . . . ?
C3 C2 C1 N1 -178.8(5) . . . . ?
C3 C4 C5 C6 0.0(11) . . . . ?
C5 C4 C3 C2 -1.4(10) . . . . ?
C37 C36 C35 N3 149.6(6) . . . . ?
C14 N1 C13 C8 -178.4(5) . . . . ?
C14 N1 C13 C12 3.4(8) . . . . ?
C14 N1 C1 O1 -0.9(8) . . . . ?
C14 N1 C1 C2 178.8(5) . . . . ?
C14 C15 C16 C17 175.2(5) . . . . ?
C14 C15 C20 C19 -175.9(5) . . . . ?
C40 C41 C36 C35 -179.4(5) . . . . ?
C40 C41 C36 C37 -1.8(9) . . . . ?
C40 C39 C38 C37 -2.6(10) . . . . ?
C21 C18 C17 C16 178.4(6) . . . . ?
C42 C39 C38 C37 177.1(6) . . . . ?
C42 C39 C40 C41 -178.4(6) . . . . ?


_olex2_date_sample_data_collection 2021-04-21
_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 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.656
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_9027
_database_code_depnum_ccdc_archive 'CCDC 2342467'
loop_
_audit_author_name
_audit_author_address
'Yu Xiong'
;Shenzhen University
China
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2021-01-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H13 Br N2 O'
_chemical_formula_sum            'C21 H13 Br N2 O'
_chemical_formula_weight         389.24
_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'

_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                   15.2781(10)
_cell_length_b                   6.7491(4)
_cell_length_c                   16.5330(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.120(6)
_cell_angle_gamma                90
_cell_volume                     1678.25(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2720
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4040
_cell_measurement_theta_min      2.4890
_shelx_estimated_absorpt_T_max   0.757
_shelx_estimated_absorpt_T_min   0.578
_exptl_absorpt_coefficient_mu    2.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11847
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.503
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  77.00   1.00    7.50    --   15.49  77.00 -60.00   61
  2  ω     -8.00  25.00   1.00    7.50    --  -16.28  77.00  90.00   33
  3  ω     -9.00  83.00   1.00    7.50    --   15.49  77.00 120.00   92
  4  ω      7.00  33.00   1.00    7.50    --  -16.28  77.00 150.00   26
  5  ω    -42.00  47.00   1.00    7.50    --  -16.28  77.00   0.00   89
  6  ω    -10.00  81.00   1.00    7.50    --   15.49  77.00-120.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0202593000
_diffrn_orient_matrix_UB_12      -0.0937578000
_diffrn_orient_matrix_UB_13      -0.0026920000
_diffrn_orient_matrix_UB_21      -0.0118291000
_diffrn_orient_matrix_UB_22      -0.0280217000
_diffrn_orient_matrix_UB_23      0.0380043000
_diffrn_orient_matrix_UB_31      -0.0408952000
_diffrn_orient_matrix_UB_32      -0.0383826000
_diffrn_orient_matrix_UB_33      -0.0211716000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2068
_reflns_number_total             2942
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.027
_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)+(0.0258P)²+0.8552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0865
_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:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C17(H17), C18(H18), C6(H6), C12(H12), C3(H3), C20(H20), C11(H11),
 C21(H21), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.68281(3) 0.93144(7) 0.76797(2) 0.07030(18) Uani 1 1 d . . . . .
N1 N 0.27709(17) 0.7723(4) 0.51185(15) 0.0435(7) Uani 1 1 d . . . . .
O1 O 0.32576(19) 0.6260(4) 0.40479(16) 0.0790(9) Uani 1 1 d . . . . .
C7 C 0.1536(2) 0.4598(5) 0.51363(18) 0.0396(8) Uani 1 1 d . . . . .
C8 C 0.1606(2) 0.6190(5) 0.57413(18) 0.0380(8) Uani 1 1 d . . . . .
C13 C 0.2222(2) 0.7726(5) 0.57160(18) 0.0407(8) Uani 1 1 d . . . . .
C9 C 0.1092(2) 0.6226(5) 0.63615(19) 0.0442(8) Uani 1 1 d . . . . .
H9 H 0.068735 0.521076 0.639114 0.053 Uiso 1 1 calc R U . . .
C2 C 0.2100(2) 0.4639(5) 0.45581(18) 0.0427(8) Uani 1 1 d . . . . .
C19 C 0.5767(2) 0.9280(5) 0.6888(2) 0.0481(9) Uani 1 1 d . . . . .
C10 C 0.1174(2) 0.7740(5) 0.6932(2) 0.0473(9) Uani 1 1 d . . . . .
C16 C 0.4222(2) 0.9289(5) 0.57327(19) 0.0436(8) Uani 1 1 d . . . . .
C17 C 0.4696(2) 0.7566(5) 0.5923(2) 0.0533(9) Uani 1 1 d . . . . .
H17 H 0.449105 0.639360 0.566062 0.064 Uiso 1 1 calc R U . . .
C1 C 0.2752(2) 0.6230(5) 0.4544(2) 0.0510(9) Uani 1 1 d . . . . .
C18 C 0.5470(2) 0.7552(5) 0.6499(2) 0.0547(10) Uani 1 1 d . . . . .
H18 H 0.578682 0.638108 0.662146 0.066 Uiso 1 1 calc R U . . .
C6 C 0.0932(2) 0.3020(5) 0.5102(2) 0.0532(9) Uani 1 1 d . . . . .
H6 H 0.055122 0.294454 0.548266 0.064 Uiso 1 1 calc R U . . .
C12 C 0.2292(2) 0.9249(5) 0.6292(2) 0.0532(9) Uani 1 1 d . . . . .
H12 H 0.269592 1.027098 0.627163 0.064 Uiso 1 1 calc R U . . .
C3 C 0.2055(2) 0.3148(6) 0.3969(2) 0.0547(10) Uani 1 1 d . . . . .
H3 H 0.243828 0.318565 0.359014 0.066 Uiso 1 1 calc R U . . .
C20 C 0.5316(3) 1.1017(5) 0.6707(2) 0.0569(10) Uani 1 1 d . . . . .
H20 H 0.552548 1.218654 0.696893 0.068 Uiso 1 1 calc R U . . .
C11 C 0.1774(2) 0.9259(5) 0.6889(2) 0.0560(10) Uani 1 1 d . . . . .
H11 H 0.182536 1.029056 0.726746 0.067 Uiso 1 1 calc R U . . .
N2 N 0.0248(2) 0.7654(5) 0.8096(2) 0.0806(11) Uani 1 1 d . . . . .
C15 C 0.3397(2) 0.9361(5) 0.5080(2) 0.0521(9) Uani 1 1 d . . . . .
H15A H 0.309191 1.060305 0.513014 0.063 Uiso 1 1 calc R U . . .
H15B H 0.357424 0.934602 0.454456 0.063 Uiso 1 1 calc R U . . .
C21 C 0.4544(2) 1.1013(5) 0.6129(2) 0.0549(10) Uani 1 1 d . . . . .
H21 H 0.423548 1.219250 0.600361 0.066 Uiso 1 1 calc R U . . .
C4 C 0.1462(3) 0.1639(6) 0.3940(2) 0.0630(11) Uani 1 1 d . . . . .
H4 H 0.143500 0.065540 0.354261 0.076 Uiso 1 1 calc R U . . .
C5 C 0.0901(2) 0.1586(6) 0.4507(2) 0.0618(10) Uani 1 1 d . . . . .
H5 H 0.049236 0.055801 0.448740 0.074 Uiso 1 1 calc R U . . .
C14 C 0.0647(3) 0.7701(5) 0.7579(2) 0.0578(10) 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
Br1 C19 1.897(3) . ?
N1 C13 1.404(4) . ?
N1 C1 1.381(4) . ?
N1 C15 1.471(4) . ?
O1 C1 1.222(4) . ?
C7 C8 1.459(4) . ?
C7 C2 1.395(4) . ?
C7 C6 1.405(4) . ?
C8 C13 1.406(4) . ?
C8 C9 1.396(4) . ?
C13 C12 1.393(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(4) . ?
C2 C1 1.468(5) . ?
C2 C3 1.393(4) . ?
C19 C18 1.369(5) . ?
C19 C20 1.367(5) . ?
C10 C11 1.386(5) . ?
C10 C14 1.449(5) . ?
C16 C17 1.376(4) . ?
C16 C15 1.510(5) . ?
C16 C21 1.383(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(5) . ?
C18 H18 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.374(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.369(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.358(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(5) . ?
C11 H11 0.9300 . ?
N2 C14 1.133(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C21 H21 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.378(5) . ?
C5 H5 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
C13 N1 C15 120.2(3) . . ?
C1 N1 C13 122.8(3) . . ?
C1 N1 C15 117.0(3) . . ?
C2 C7 C8 118.4(3) . . ?
C2 C7 C6 117.9(3) . . ?
C6 C7 C8 123.6(3) . . ?
C13 C8 C7 119.4(3) . . ?
C9 C8 C7 122.3(3) . . ?
C9 C8 C13 118.3(3) . . ?
N1 C13 C8 120.4(3) . . ?
C12 C13 N1 119.9(3) . . ?
C12 C13 C8 119.7(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C7 C2 C1 121.8(3) . . ?
C3 C2 C7 120.3(3) . . ?
C3 C2 C1 117.9(3) . . ?
C18 C19 Br1 120.4(3) . . ?
C20 C19 Br1 118.5(3) . . ?
C20 C19 C18 121.0(3) . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 C14 119.7(3) . . ?
C11 C10 C14 120.7(3) . . ?
C17 C16 C15 122.0(3) . . ?
C17 C16 C21 118.3(3) . . ?
C21 C16 C15 119.6(3) . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
N1 C1 C2 117.1(3) . . ?
O1 C1 N1 120.7(3) . . ?
O1 C1 C2 122.2(3) . . ?
C19 C18 C17 119.3(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C13 C12 H12 119.6 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.1(3) . . ?
C21 C20 H20 120.4 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
N1 C15 C16 114.4(3) . . ?
N1 C15 H15A 108.7 . . ?
N1 C15 H15B 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.3(3) . . ?
C20 C21 H21 119.4 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(4) . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N2 C14 C10 178.7(4) . . ?

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 C19 C18 C17 -179.9(2) . . . . ?
Br1 C19 C20 C21 179.7(2) . . . . ?
N1 C13 C12 C11 -178.8(3) . . . . ?
C7 C8 C13 N1 -0.5(4) . . . . ?
C7 C8 C13 C12 -179.9(3) . . . . ?
C7 C8 C9 C10 179.5(3) . . . . ?
C7 C2 C1 N1 -1.5(5) . . . . ?
C7 C2 C1 O1 178.8(3) . . . . ?
C7 C2 C3 C4 0.5(5) . . . . ?
C7 C6 C5 C4 0.8(6) . . . . ?
C8 C7 C2 C1 -0.1(4) . . . . ?
C8 C7 C2 C3 -180.0(3) . . . . ?
C8 C7 C6 C5 179.3(3) . . . . ?
C8 C13 C12 C11 0.6(5) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C8 C9 C10 C14 -178.4(3) . . . . ?
C13 N1 C1 O1 -178.1(3) . . . . ?
C13 N1 C1 C2 2.2(5) . . . . ?
C13 N1 C15 C16 76.5(4) . . . . ?
C13 C8 C9 C10 0.9(5) . . . . ?
C13 C12 C11 C10 0.4(5) . . . . ?
C9 C8 C13 N1 178.1(3) . . . . ?
C9 C8 C13 C12 -1.3(4) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C2 C7 C8 C13 1.1(4) . . . . ?
C2 C7 C8 C9 -177.5(3) . . . . ?
C2 C7 C6 C5 -0.6(5) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C19 C20 C21 C16 0.0(5) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C17 C16 C15 N1 45.2(4) . . . . ?
C17 C16 C21 C20 -0.6(5) . . . . ?
C1 N1 C13 C8 -1.3(5) . . . . ?
C1 N1 C13 C12 178.2(3) . . . . ?
C1 N1 C15 C16 -103.9(3) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C6 C7 C8 C13 -178.8(3) . . . . ?
C6 C7 C8 C9 2.6(5) . . . . ?
C6 C7 C2 C1 179.8(3) . . . . ?
C6 C7 C2 C3 0.0(5) . . . . ?
C3 C2 C1 N1 178.3(3) . . . . ?
C3 C2 C1 O1 -1.3(5) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C20 C19 C18 C17 -0.9(5) . . . . ?
C15 N1 C13 C8 178.3(3) . . . . ?
C15 N1 C13 C12 -2.3(4) . . . . ?
C15 N1 C1 O1 2.3(5) . . . . ?
C15 N1 C1 C2 -177.4(3) . . . . ?
C15 C16 C17 C18 177.3(3) . . . . ?
C15 C16 C21 C20 -177.5(3) . . . . ?
C21 C16 C17 C18 0.4(5) . . . . ?
C21 C16 C15 N1 -138.0(3) . . . . ?
C14 C10 C11 C12 177.7(3) . . . . ?


_olex2_date_sample_data_collection 2021-01-30
_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 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.850
