# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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 
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data_px-6-25-1
_audit_block_doi                 10.5517/ccdc.csd.cc285kkl
_database_code_depnum_ccdc_archive 'CCDC 2090719'
loop_
_audit_author_name
_audit_author_address
'Xing Peng'
;TianJin University
China
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2021-05-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 Br N2'
_chemical_formula_sum            'C20 H21 Br N2'
_chemical_formula_weight         369.30
_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'

_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                   7.6106(9)
_cell_length_b                   7.0096(9)
_cell_length_c                   35.036(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.871(4)
_cell_angle_gamma                90
_cell_volume                     1864.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5205
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.23
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.733
_shelx_estimated_absorpt_T_min   0.539
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5253
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1225 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.7042.
The λ/2 correction factor is Not present.
;
_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    1.315
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            40261
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.587
_diffrn_reflns_theta_min         2.331
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2097
_reflns_number_total             5233
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         5233
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1705
_refine_ls_R_factor_gt           0.0616
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0845P)²+0.4353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1957
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C17, C20, C18, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3. Uiso/Uaniso restraints and constraints
C17 \\sim C20 \\sim C18 \\sim C19: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Uanis(C17) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C12(H12), C5(H5), C13(H13), C2(H2), C6(H6), C16(H16), C15(H15)
4.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_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 0.69903(7) 0.30199(11) 0.92329(2) 0.1266(3) Uani 1 1 d . . . . .
N2 N 0.4815(3) 0.4733(4) 0.73527(7) 0.0540(7) Uani 1 1 d . . . . .
N1 N 0.5251(3) 0.6045(4) 0.76331(7) 0.0546(7) Uani 1 1 d . . . . .
C10 C 0.4587(4) 0.5739(4) 0.70347(9) 0.0522(8) Uani 1 1 d . . . . .
C4 C 0.5653(4) 0.5393(5) 0.80094(9) 0.0561(8) Uani 1 1 d . . . . .
C11 C 0.4109(4) 0.4846(5) 0.66641(9) 0.0562(8) Uani 1 1 d . . . . .
C3 C 0.4716(5) 0.3860(5) 0.81472(10) 0.0615(9) Uani 1 1 d . . . . .
H3 H 0.380528 0.331710 0.799339 0.074 Uiso 1 1 calc R U . . .
C9 C 0.4864(4) 0.7704(5) 0.71080(11) 0.0629(9) Uani 1 1 d . . . . .
H9 H 0.478777 0.868704 0.692928 0.075 Uiso 1 1 calc R U . . .
C8 C 0.5262(4) 0.7877(5) 0.74877(11) 0.0591(9) Uani 1 1 d . . . . .
C12 C 0.3315(5) 0.3058(5) 0.66338(10) 0.0646(9) Uani 1 1 d . . . . .
H12 H 0.308703 0.238756 0.685407 0.078 Uiso 1 1 calc R U . . .
C5 C 0.6990(5) 0.6196(6) 0.82416(11) 0.0730(10) Uani 1 1 d . . . . .
H5 H 0.764354 0.720147 0.815140 0.088 Uiso 1 1 calc R U . . .
C13 C 0.2868(5) 0.2277(6) 0.62816(11) 0.0762(11) Uani 1 1 d . . . . .
H13 H 0.232475 0.108764 0.627122 0.091 Uiso 1 1 calc R U . . .
C14 C 0.3185(5) 0.3173(6) 0.59410(11) 0.0734(10) Uani 1 1 d . . . . .
C2 C 0.5118(5) 0.3145(5) 0.85055(11) 0.0735(10) Uani 1 1 d . . . . .
H2 H 0.450490 0.210441 0.859372 0.088 Uiso 1 1 calc R U . . .
C7 C 0.5525(5) 0.9634(5) 0.77284(12) 0.0773(11) Uani 1 1 d . . . . .
H7A H 0.495292 0.947397 0.796224 0.116 Uiso 1 1 calc R U . . .
H7B H 0.502867 1.071334 0.759126 0.116 Uiso 1 1 calc R U . . .
H7C H 0.676160 0.983968 0.778579 0.116 Uiso 1 1 calc R U . . .
C6 C 0.7359(5) 0.5515(7) 0.86052(12) 0.0863(12) Uani 1 1 d . . . . .
H6 H 0.823204 0.609011 0.876448 0.104 Uiso 1 1 calc R U . . .
C1 C 0.6442(6) 0.3987(7) 0.87343(11) 0.0814(12) Uani 1 1 d . . . . .
C16 C 0.4418(6) 0.5758(6) 0.63282(11) 0.0905(13) Uani 1 1 d . . . . .
H16 H 0.495070 0.695304 0.633840 0.109 Uiso 1 1 calc R U . . .
C15 C 0.3961(6) 0.4954(7) 0.59766(11) 0.0967(14) Uani 1 1 d . . . . .
H15 H 0.418042 0.562962 0.575640 0.116 Uiso 1 1 calc R U . . .
C17 C 0.2698(8) 0.2285(8) 0.55496(14) 0.1073(15) Uani 1 1 d . U . . .
C19 C 0.2658(8) 0.0129(8) 0.55662(14) 0.1268(18) Uani 1 1 d . U . . .
H19A H 0.383108 -0.034644 0.562036 0.190 Uiso 1 1 calc R U . . .
H19B H 0.219091 -0.036440 0.532458 0.190 Uiso 1 1 calc R U . . .
H19C H 0.192568 -0.027052 0.576403 0.190 Uiso 1 1 calc R U . . .
C18 C 0.0889(11) 0.2917(11) 0.5423(2) 0.201(4) Uani 1 1 d . U . . .
H18A H 0.017150 0.292443 0.563856 0.302 Uiso 1 1 calc R U . . .
H18B H 0.039290 0.205539 0.523233 0.302 Uiso 1 1 calc R U . . .
H18C H 0.093320 0.417858 0.531807 0.302 Uiso 1 1 calc R U . . .
C20 C 0.4051(13) 0.2828(12) 0.52702(19) 0.203(4) Uani 1 1 d . U . . .
H20A H 0.374327 0.403859 0.515621 0.305 Uiso 1 1 calc R U . . .
H20B H 0.407386 0.187424 0.507406 0.305 Uiso 1 1 calc R U . . .
H20C H 0.519212 0.291570 0.540360 0.305 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 C1 1.894(4) . ?
N2 N1 1.370(3) . ?
N2 C10 1.320(4) . ?
N1 C4 1.409(4) . ?
N1 C8 1.382(4) . ?
C10 C11 1.465(4) . ?
C10 C9 1.414(5) . ?
C4 C3 1.394(5) . ?
C4 C5 1.379(5) . ?
C11 C12 1.392(4) . ?
C11 C16 1.374(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.367(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.350(5) . ?
C8 C7 1.498(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(5) . ?
C14 C15 1.383(6) . ?
C14 C17 1.528(6) . ?
C2 H2 0.9300 . ?
C2 C1 1.377(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 H6 0.9300 . ?
C6 C1 1.372(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.378(5) . ?
C15 H15 0.9300 . ?
C17 C19 1.513(7) . ?
C17 C18 1.485(9) . ?
C17 C20 1.516(9) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N2 N1 105.0(3) . . ?
N2 N1 C4 118.7(3) . . ?
N2 N1 C8 111.5(3) . . ?
C8 N1 C4 129.8(3) . . ?
N2 C10 C11 122.0(3) . . ?
N2 C10 C9 111.0(3) . . ?
C9 C10 C11 127.0(3) . . ?
C3 C4 N1 119.3(3) . . ?
C5 C4 N1 121.6(3) . . ?
C5 C4 C3 119.0(3) . . ?
C12 C11 C10 122.2(3) . . ?
C16 C11 C10 120.9(3) . . ?
C16 C11 C12 116.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C10 C9 H9 126.7 . . ?
C8 C9 C10 106.7(3) . . ?
C8 C9 H9 126.7 . . ?
N1 C8 C7 124.1(3) . . ?
C9 C8 N1 105.9(3) . . ?
C9 C8 C7 129.8(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C12 C13 H13 118.4 . . ?
C12 C13 C14 123.2(3) . . ?
C14 C13 H13 118.4 . . ?
C13 C14 C17 122.9(4) . . ?
C15 C14 C13 115.5(4) . . ?
C15 C14 C17 121.6(4) . . ?
C3 C2 H2 120.4 . . ?
C3 C2 C1 119.1(4) . . ?
C1 C2 H2 120.4 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C1 120.1(4) . . ?
C1 C6 H6 120.0 . . ?
C2 C1 Br1 119.4(4) . . ?
C6 C1 Br1 119.9(3) . . ?
C6 C1 C2 120.8(4) . . ?
C11 C16 H16 119.1 . . ?
C11 C16 C15 121.9(4) . . ?
C15 C16 H16 119.1 . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 122.0(4) . . ?
C16 C15 H15 119.0 . . ?
C19 C17 C14 112.1(4) . . ?
C19 C17 C20 107.0(6) . . ?
C18 C17 C14 108.0(5) . . ?
C18 C17 C19 106.8(5) . . ?
C18 C17 C20 112.9(6) . . ?
C20 C17 C14 110.1(5) . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C4 C3 -37.2(4) . . . . ?
N2 N1 C4 C5 140.8(3) . . . . ?
N2 N1 C8 C9 -1.4(3) . . . . ?
N2 N1 C8 C7 174.1(3) . . . . ?
N2 C10 C11 C12 21.5(5) . . . . ?
N2 C10 C11 C16 -159.0(3) . . . . ?
N2 C10 C9 C8 -0.5(4) . . . . ?
N1 N2 C10 C11 179.7(3) . . . . ?
N1 N2 C10 C9 -0.3(3) . . . . ?
N1 C4 C3 C2 177.4(3) . . . . ?
N1 C4 C5 C6 -179.3(3) . . . . ?
C10 N2 N1 C4 -177.4(3) . . . . ?
C10 N2 N1 C8 1.1(3) . . . . ?
C10 C11 C12 C13 179.2(3) . . . . ?
C10 C11 C16 C15 -179.2(4) . . . . ?
C10 C9 C8 N1 1.1(4) . . . . ?
C10 C9 C8 C7 -174.0(3) . . . . ?
C4 N1 C8 C9 176.9(3) . . . . ?
C4 N1 C8 C7 -7.6(5) . . . . ?
C4 C3 C2 C1 1.4(5) . . . . ?
C4 C5 C6 C1 2.4(6) . . . . ?
C11 C10 C9 C8 179.4(3) . . . . ?
C11 C12 C13 C14 0.9(6) . . . . ?
C11 C16 C15 C14 -0.8(8) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C3 C2 C1 Br1 179.4(3) . . . . ?
C3 C2 C1 C6 -0.4(6) . . . . ?
C9 C10 C11 C12 -158.4(3) . . . . ?
C9 C10 C11 C16 21.0(5) . . . . ?
C8 N1 C4 C3 144.6(3) . . . . ?
C8 N1 C4 C5 -37.4(5) . . . . ?
C12 C11 C16 C15 0.3(6) . . . . ?
C12 C13 C14 C15 -1.3(7) . . . . ?
C12 C13 C14 C17 179.4(5) . . . . ?
C5 C4 C3 C2 -0.5(5) . . . . ?
C5 C6 C1 Br1 178.7(3) . . . . ?
C5 C6 C1 C2 -1.5(6) . . . . ?
C13 C14 C15 C16 1.3(7) . . . . ?
C13 C14 C17 C19 -26.5(7) . . . . ?
C13 C14 C17 C18 90.8(7) . . . . ?
C13 C14 C17 C20 -145.5(6) . . . . ?
C16 C11 C12 C13 -0.3(5) . . . . ?
C15 C14 C17 C19 154.3(5) . . . . ?
C15 C14 C17 C18 -88.4(6) . . . . ?
C15 C14 C17 C20 35.3(8) . . . . ?
C17 C14 C15 C16 -179.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p2
_audit_block_doi                 10.5517/ccdc.csd.cc285kjk
_database_code_depnum_ccdc_archive 'CCDC 2090718'
loop_
_audit_author_name
_audit_author_address
'Xing Peng'
;TianJin University
China
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H7 N3 O2'
_chemical_formula_sum            'C9 H7 N3 O2'
_chemical_formula_weight         189.18
_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           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                   6.9272(4)
_cell_length_b                   10.2579(6)
_cell_length_c                   11.4955(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.872(2)
_cell_angle_gamma                90
_cell_volume                     814.99(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6838
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.57
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1380
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15108
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.664
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1245
_reflns_number_total             1437
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.079
_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)+(0.0844P)²+0.0855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1281
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E)
;
_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
O001 O 0.60320(17) 0.74036(10) 0.18344(9) 0.0322(4) Uani 1 1 d . . . . .
O O 0.77343(17) 0.56323(11) 0.18446(9) 0.0317(4) Uani 1 1 d . . . . .
N003 N 0.66431(17) 0.61298(11) 0.72119(10) 0.0191(3) Uani 1 1 d . . . . .
N004 N 0.58342(18) 0.70990(12) 0.78368(10) 0.0236(4) Uani 1 1 d . . . . .
N005 N 0.68544(18) 0.64858(12) 0.23453(10) 0.0233(4) Uani 1 1 d . . . . .
C006 C 0.6699(2) 0.62351(13) 0.59934(12) 0.0179(4) Uani 1 1 d . . . . .
C007 C 0.7537(2) 0.52361(14) 0.53728(12) 0.0209(4) Uani 1 1 d . . . . .
H007 H 0.807213 0.451606 0.576642 0.025 Uiso 1 1 calc R U . . .
C008 C 0.6787(2) 0.63986(13) 0.36089(12) 0.0197(4) Uani 1 1 d . . . . .
C009 C 0.5935(2) 0.73995(13) 0.42029(13) 0.0209(4) Uani 1 1 d . . . . .
H009 H 0.540764 0.811741 0.380274 0.025 Uiso 1 1 calc R U . . .
C00A C 0.5885(2) 0.73110(13) 0.54009(12) 0.0203(4) Uani 1 1 d . . . . .
H00A H 0.530762 0.796921 0.581227 0.024 Uiso 1 1 calc R U . . .
C00B C 0.7573(2) 0.53176(13) 0.41758(12) 0.0210(4) Uani 1 1 d . . . . .
H00B H 0.811905 0.465243 0.375720 0.025 Uiso 1 1 calc R U . . .
C00C C 0.7266(2) 0.51257(14) 0.79166(12) 0.0221(4) Uani 1 1 d . . . . .
H00C H 0.786200 0.436494 0.768524 0.027 Uiso 1 1 calc R U . . .
C00D C 0.5980(2) 0.66641(14) 0.89221(12) 0.0239(4) Uani 1 1 d . . . . .
H00D H 0.554491 0.712247 0.955165 0.029 Uiso 1 1 calc R U . . .
C00E C 0.6857(2) 0.54423(14) 0.90178(12) 0.0236(4) Uani 1 1 d . . . . .
H00E H 0.710628 0.495105 0.969113 0.028 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
O001 N005 1.2290(16) . ?
O N005 1.2316(16) . ?
N003 N004 1.3685(16) . ?
N003 C006 1.4080(18) . ?
N003 C00C 1.3625(18) . ?
N004 C00D 1.3224(18) . ?
N005 C008 1.4593(18) . ?
C006 C007 1.3973(19) . ?
C006 C00A 1.396(2) . ?
C007 H007 0.9300 . ?
C007 C00B 1.3804(19) . ?
C008 C009 1.387(2) . ?
C008 C00B 1.379(2) . ?
C009 H009 0.9300 . ?
C009 C00A 1.383(2) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00E 1.355(2) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.394(2) . ?
C00E H00E 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
N004 N003 C006 120.41(11) . . ?
C00C N003 N004 111.20(11) . . ?
C00C N003 C006 128.36(11) . . ?
C00D N004 N003 104.03(12) . . ?
O001 N005 O 123.32(12) . . ?
O001 N005 C008 118.54(12) . . ?
O N005 C008 118.14(12) . . ?
C007 C006 N003 119.47(12) . . ?
C00A C006 N003 120.59(12) . . ?
C00A C006 C007 119.93(13) . . ?
C006 C007 H007 120.0 . . ?
C00B C007 C006 120.03(13) . . ?
C00B C007 H007 120.0 . . ?
C009 C008 N005 119.21(13) . . ?
C00B C008 N005 118.79(12) . . ?
C00B C008 C009 122.01(13) . . ?
C008 C009 H009 120.6 . . ?
C00A C009 C008 118.81(13) . . ?
C00A C009 H009 120.6 . . ?
C006 C00A H00A 120.0 . . ?
C009 C00A C006 120.09(13) . . ?
C009 C00A H00A 120.0 . . ?
C007 C00B H00B 120.4 . . ?
C008 C00B C007 119.12(12) . . ?
C008 C00B H00B 120.4 . . ?
N003 C00C H00C 126.4 . . ?
C00E C00C N003 107.23(13) . . ?
C00E C00C H00C 126.4 . . ?
N004 C00D H00D 123.7 . . ?
N004 C00D C00E 112.51(13) . . ?
C00E C00D H00D 123.7 . . ?
C00C C00E C00D 105.03(12) . . ?
C00C C00E H00E 127.5 . . ?
C00D C00E H00E 127.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 N005 C008 C009 -5.00(19) . . . . ?
O001 N005 C008 C00B 174.87(12) . . . . ?
O N005 C008 C009 175.05(12) . . . . ?
O N005 C008 C00B -5.08(19) . . . . ?
N003 N004 C00D C00E -0.05(17) . . . . ?
N003 C006 C007 C00B 178.94(12) . . . . ?
N003 C006 C00A C009 -179.53(12) . . . . ?
N003 C00C C00E C00D -0.11(16) . . . . ?
N004 N003 C006 C007 179.78(12) . . . . ?
N004 N003 C006 C00A -1.7(2) . . . . ?
N004 N003 C00C C00E 0.09(17) . . . . ?
N004 C00D C00E C00C 0.10(17) . . . . ?
N005 C008 C009 C00A -179.76(12) . . . . ?
N005 C008 C00B C007 179.16(12) . . . . ?
C006 N003 N004 C00D 178.22(12) . . . . ?
C006 N003 C00C C00E -177.98(13) . . . . ?
C006 C007 C00B C008 0.6(2) . . . . ?
C007 C006 C00A C009 -1.0(2) . . . . ?
C008 C009 C00A C006 0.6(2) . . . . ?
C009 C008 C00B C007 -1.0(2) . . . . ?
C00A C006 C007 C00B 0.4(2) . . . . ?
C00B C008 C009 C00A 0.4(2) . . . . ?
C00C N003 N004 C00D -0.02(16) . . . . ?
C00C N003 C006 C007 -2.3(2) . . . . ?
C00C N003 C006 C00A 176.17(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p-1
_audit_block_doi                 10.5517/ccdc.csd.cc285klm
_database_code_depnum_ccdc_archive 'CCDC 2090720'
loop_
_audit_author_name
_audit_author_address
'Xing Peng'
;TianJin University
China
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2021-05-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Br N2'
_chemical_formula_sum            'C15 H11 Br N2'
_chemical_formula_weight         299.17
_chemical_absolute_configuration ?
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.3864(19)
_cell_length_b                   26.396(6)
_cell_length_c                   5.7779(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1279.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1726
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      16.49
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   0.807
_shelx_estimated_absorpt_T_min   0.428
_exptl_absorpt_coefficient_mu    3.196
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1482 before and 0.0832 after correction.
The Ratio of minimum to maximum transmission is 0.7823.
The λ/2 correction factor is Not present.
;
_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    1.554
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1607
_diffrn_reflns_av_unetI/netI     0.1292
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            17590
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.021
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         2.548
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1053
_reflns_number_total             2241
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2241
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.015
_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)+0.1744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1333
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.01(3)
 -0.01(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C11(H11), C15(H15), C14(H14), C6(H6), C1(H1), C2(H2),
 C3(H3), C4(H4), C9(H9)
3.b Fitted hexagon refined as free rotating group:
 C12(C11,C10,C15,C14,C13), C5(C6,C1,C2,C3,C4)
;
_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 0.45632(15) 0.17474(4) 0.4938(4) 0.0985(5) Uani 1 1 d . . . . .
N2 N 0.7938(11) -0.0134(4) 0.1513(14) 0.064(3) Uani 1 1 d . . . . .
N1 N 0.8145(10) -0.0534(4) 0.2950(15) 0.067(3) Uani 1 1 d . . . . .
C8 C 0.9292(14) -0.0686(5) -0.052(2) 0.076(4) Uani 1 1 d . . . . .
H8 H 0.984684 -0.084834 -0.169528 0.091 Uiso 1 1 calc R U . . .
C7 C 0.8980(14) -0.0884(5) 0.179(2) 0.067(3) Uani 1 1 d . . . . .
C12 C 0.5476(8) 0.0715(3) 0.5070(10) 0.067(2) Uani 1 1 d G . . . .
H12 H 0.492140 0.070451 0.646274 0.080 Uiso 1 1 calc R U . . .
C11 C 0.6260(9) 0.0285(2) 0.4273(11) 0.067(3) Uani 1 1 d G . . . .
H11 H 0.623015 -0.001301 0.513268 0.081 Uiso 1 1 calc R U . . .
C10 C 0.7089(8) 0.0300(3) 0.2190(12) 0.056(3) Uani 1 1 d G . . . .
C15 C 0.7133(8) 0.0745(3) 0.0905(10) 0.072(4) Uani 1 1 d G . . . .
H15 H 0.768767 0.075457 -0.048829 0.087 Uiso 1 1 calc R U . . .
C14 C 0.6349(10) 0.1174(2) 0.1702(13) 0.073(3) Uani 1 1 d G . . . .
H14 H 0.637894 0.147210 0.084172 0.087 Uiso 1 1 calc R U . . .
C13 C 0.5520(9) 0.1159(2) 0.3784(14) 0.069(3) Uani 1 1 d G . . . .
C5 C 0.9492(10) -0.1361(2) 0.2779(14) 0.061(3) Uani 1 1 d G . . . .
C6 C 0.8751(8) -0.1540(3) 0.4771(14) 0.072(3) Uani 1 1 d G . . . .
H6 H 0.791718 -0.135787 0.543017 0.086 Uiso 1 1 calc R U . . .
C1 C 0.9258(12) -0.1990(3) 0.5777(13) 0.085(4) Uani 1 1 d G . . . .
H1 H 0.876241 -0.210977 0.710893 0.102 Uiso 1 1 calc R U . . .
C2 C 1.0505(12) -0.2262(2) 0.479(2) 0.087(3) Uani 1 1 d G . . . .
H2 H 1.084348 -0.256330 0.546402 0.104 Uiso 1 1 calc R U . . .
C3 C 1.1245(8) -0.2083(4) 0.280(2) 0.099(4) Uani 1 1 d G . . . .
H3 H 1.207934 -0.226493 0.214035 0.119 Uiso 1 1 calc R U . . .
C4 C 1.0739(10) -0.1633(4) 0.1794(13) 0.085(4) Uani 1 1 d G . . . .
H4 H 1.123413 -0.151303 0.046156 0.102 Uiso 1 1 calc R U . . .
C9 C 0.8630(15) -0.0226(5) -0.0618(17) 0.070(3) Uani 1 1 d . . . . .
H9 H 0.863427 -0.000804 -0.188316 0.084 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 C13 1.870(6) . ?
N2 N1 1.352(11) . ?
N2 C10 1.405(11) . ?
N2 C9 1.382(12) . ?
N1 C7 1.339(14) . ?
C8 H8 0.9300 . ?
C8 C7 1.454(18) . ?
C8 C9 1.336(14) . ?
C7 C5 1.449(13) . ?
C12 H12 0.9300 . ?
C12 C11 1.3900 . ?
C12 C13 1.3900 . ?
C11 H11 0.9300 . ?
C11 C10 1.3900 . ?
C10 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C14 H14 0.9300 . ?
C14 C13 1.3900 . ?
C5 C6 1.3900 . ?
C5 C4 1.3900 . ?
C6 H6 0.9300 . ?
C6 C1 1.3900 . ?
C1 H1 0.9300 . ?
C1 C2 1.3900 . ?
C2 H2 0.9300 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N2 C10 122.0(8) . . ?
N1 N2 C9 110.9(9) . . ?
C9 N2 C10 127.1(10) . . ?
C7 N1 N2 107.3(9) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
C9 C8 C7 107.0(11) . . ?
N1 C7 C8 107.8(11) . . ?
N1 C7 C5 123.8(11) . . ?
C5 C7 C8 128.4(13) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 N2 118.1(7) . . ?
C15 C10 N2 121.8(7) . . ?
C15 C10 C11 120.0 . . ?
C10 C15 H15 120.0 . . ?
C10 C15 C14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C12 C13 Br1 119.9(5) . . ?
C14 C13 Br1 120.0(5) . . ?
C14 C13 C12 120.0 . . ?
C6 C5 C7 119.3(9) . . ?
C6 C5 C4 120.0 . . ?
C4 C5 C7 120.7(9) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.0 . . ?
C1 C6 H6 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
N2 C9 H9 126.5 . . ?
C8 C9 N2 107.1(10) . . ?
C8 C9 H9 126.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C7 C8 -0.4(11) . . . . ?
N2 N1 C7 C5 177.7(9) . . . . ?
N2 C10 C15 C14 -176.4(7) . . . . ?
N1 N2 C10 C11 -9.1(10) . . . . ?
N1 N2 C10 C15 167.4(6) . . . . ?
N1 N2 C9 C8 -0.5(12) . . . . ?
N1 C7 C5 C6 18.5(13) . . . . ?
N1 C7 C5 C4 -159.8(8) . . . . ?
C8 C7 C5 C6 -163.8(9) . . . . ?
C8 C7 C5 C4 17.9(14) . . . . ?
C7 C8 C9 N2 0.2(13) . . . . ?
C7 C5 C6 C1 -178.3(8) . . . . ?
C7 C5 C4 C3 178.3(8) . . . . ?
C12 C11 C10 N2 176.5(7) . . . . ?
C12 C11 C10 C15 0.0 . . . . ?
C11 C12 C13 Br1 -176.5(5) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C10 N2 N1 C7 179.3(8) . . . . ?
C10 N2 C9 C8 -179.2(9) . . . . ?
C10 C15 C14 C13 0.0 . . . . ?
C15 C14 C13 Br1 176.5(5) . . . . ?
C15 C14 C13 C12 0.0 . . . . ?
C13 C12 C11 C10 0.0 . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C9 N2 N1 C7 0.6(11) . . . . ?
C9 N2 C10 C11 169.5(8) . . . . ?
C9 N2 C10 C15 -14.1(11) . . . . ?
C9 C8 C7 N1 0.1(13) . . . . ?
C9 C8 C7 C5 -177.9(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.01(3)
2 -0.01(3)

