# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_anna_stas99604_5
_database_code_depnum_ccdc_archive 'CCDC 1983237'
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-03-05 downloaded from the CCDC.
;
_audit_creation_date             2020-02-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
''
''
''
''
mrubin@ku.edu
_chemical_name_common            ?
_chemical_name_systematic        4-(5-bromopyrimidin-4-yl)phenol
_chemical_formula_moiety         'C10 H7 Br N2 O'
_chemical_formula_sum            'C10 H7 Br N2 O'
_chemical_formula_weight         251.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0376(2)
_cell_length_b                   9.5049(2)
_cell_length_c                   11.5608(2)
_cell_angle_alpha                77.439(2)
_cell_angle_beta                 76.725(2)
_cell_angle_gamma                87.542(2)
_cell_volume                     943.39(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15528
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      75.9270
_cell_measurement_theta_min      3.9860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.662
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.768
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -6 -2 0.0995
-2 5 4 0.1163
-6 1 0 0.1152
-3 -2 5 0.1316
5 -2 4 0.0762
-2 3 -6 0.1588
-5 2 -3 0.1297
-2 -5 -5 0.1086
2 5 4 0.1134
4 3 -3 0.2605
-3 5 1 0.1122
3 3 -4 0.2500
-1 5 -2 0.1470
4 0 -4 0.2685
0 0 -7 0.2294
-4 -1 -7 0.1198
-5 -2 1 0.1096
-4 -4 -5 0.0872

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.214
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.5357 -6.0587 -2.3345 0.2312 0.9672 0.1056
-1.5195 5.4138 3.6283 -0.2281 -0.9518 0.2050
-5.7350 0.6440 -0.3773 0.6236 -0.4791 0.6177
-2.5197 -2.0613 4.8034 -0.1122 0.0837 0.9902
4.5430 -2.3203 4.1359 -0.7922 0.6067 0.0657
-1.9432 2.8275 -5.6589 0.6411 -0.4898 -0.5908
-5.3108 1.8116 -2.9253 0.7777 -0.5962 0.1994
-1.9000 -5.3422 -4.8117 0.6857 0.7235 0.0791
2.1446 5.4348 4.4152 -0.6792 -0.7164 -0.1598
3.5471 3.0758 -2.7928 -0.1808 -0.1884 -0.9653
-3.2947 4.9069 1.0907 0.1804 -0.9675 0.1774
2.6473 2.7534 -4.1459 0.0329 -0.1858 -0.9820
-0.5335 5.4134 -2.0786 0.1519 -0.8210 -0.5503
4.0411 -0.3875 -4.0873 -0.0717 0.3767 -0.9236
-0.3646 0.4844 -7.0783 0.6306 -0.0174 -0.7760
-3.5324 -0.9138 -6.8579 0.9646 -0.0250 -0.2624
-4.8886 -2.2386 1.2315 0.4413 -0.0096 0.8973
-3.5449 -4.3691 -5.0358 0.8627 0.4697 0.1873

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19731
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.180
_diffrn_reflns_theta_min         4.022
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.35 -38.00  60.00   99
  2  ω   -116.00 -17.00   1.00    1.00    --  -41.35 -38.00 -60.00   99
  3  ω    -66.00  33.00   1.00    1.00    --  -41.35  38.00-120.00   99
  4  ω     23.00  97.00   1.00    1.00    --   41.35-125.00-120.00   74
  5  ω      1.00  82.00   1.00    1.00    --   41.35 -99.00 -30.00   81
  6  ω     23.00  97.00   1.00    1.00    --   41.35-125.00 120.00   74
  7  ω     79.00 178.00   1.00    1.00    --  112.00  77.00-120.00   99
  8  ω     86.00 178.00   1.00    1.00    --  112.00  45.00 -30.00   92
  9  ω     39.00 138.00   1.00    1.00    --  112.00 -45.00 150.00   99
 10  ω     36.00 145.00   1.00    1.00    --  112.00 -77.00-180.00  109
 11  ω     30.00 165.00   1.00    1.00    --  112.00 -15.00 -30.00  135
 12  ω     79.00 178.00   1.00    1.00    --  112.00  77.00 -90.00   99
 13  ω     36.00 116.00   1.00    1.00    --  112.00-111.00 -90.00   80
 14  ω     40.00 141.00   1.00    1.00    --  112.00 -61.00   0.00  101
 15  ω     84.00 178.00   1.00    1.00    --  112.00  30.00-120.00   94
 16  ω    100.00 178.00   1.00    1.00    --  112.00 111.00  90.00   78
 17  ω     86.00 178.00   1.00    1.00    --  112.00  45.00-180.00   92
 18  ω     36.00 116.00   1.00    1.00    --  112.00-111.00   0.00   80
 19  ω     29.00 109.00   1.00    1.00    --  112.00 -94.00   0.00   80
 20  ω     36.00 116.00   1.00    1.00    --  112.00-111.00-150.00   80
 21  ω     29.00 109.00   1.00    1.00    --  112.00 -94.00-180.00   80
 22  ω     84.00 178.00   1.00    1.00    --  112.00  30.00 -60.00   94
 23  ω     39.00 138.00   1.00    1.00    --  112.00 -45.00  90.00   99
 24  ω     36.00 145.00   1.00    1.00    --  112.00 -77.00   0.00  109
 25  ω     36.00 145.00   1.00    1.00    --  112.00 -77.00  90.00  109
 26  ω     36.00 116.00   1.00    1.00    --  112.00-111.00 120.00   80
 27  ω     29.00 109.00   1.00    1.00    --  112.00 -94.00  60.00   80
 28  ω     83.00 178.00   1.00    1.00    --  112.00  61.00  90.00   95
 29  ω     40.00 141.00   1.00    1.00    --  112.00 -61.00-150.00  101
 30  ω     36.00 145.00   1.00    1.00    --  112.00 -77.00-120.00  109
 31  ω    100.00 178.00   1.00    1.00    --  112.00 111.00-150.00   78
 32  ω     29.00 109.00   1.00    1.00    --  112.00 -94.00 120.00   80
 33  ω     83.00 178.00   1.00    1.00    --  112.00  61.00 150.00   95
 34  ω   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00-150.00  108
 35  ω   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00 -90.00  108
 36  ω      9.00  71.00   1.00    1.00    --   41.35  77.00  30.00   62
 37  ω      6.00  34.00   1.00    1.00    --   41.35  87.00 112.93   28
 38  ω     30.00  56.00   1.00    1.00    --  112.00 -94.00 -90.00   26
 39  ω     73.00  99.00   1.00    1.00    --  112.00 -94.00 -90.00   26
 40  ω     35.00  61.00   1.00    1.00    --  112.00 -94.00  30.00   26
 41  ω     79.00 105.00   1.00    1.00    --  112.00-111.00-120.00   26
 42  ω     80.00 106.00   1.00    1.00    --  112.00 178.00 -60.00   26
 43  ω    153.00 178.00   1.00    1.00    --  112.00   0.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1048254000
_diffrn_orient_matrix_UB_12      -0.0147954000
_diffrn_orient_matrix_UB_13      -0.0846953000
_diffrn_orient_matrix_UB_21      0.0675192000
_diffrn_orient_matrix_UB_22      -0.1493290000
_diffrn_orient_matrix_UB_23      -0.0112391000
_diffrn_orient_matrix_UB_31      -0.1230006000
_diffrn_orient_matrix_UB_32      -0.0711181000
_diffrn_orient_matrix_UB_33      0.1110948000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3850
_reflns_number_total             3943
_reflns_odcompleteness_completeness 98.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     76.86
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.0035(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.084
_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)+(0.0393P)²+1.3812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0780
_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:
 C17(H17), C16(H16), C12(H12), C11(H11), C6(H6), C19(H19), C7(H7), C1(H1A),
 C10(H10), C20(H20), C2(H2A), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.56997(2) 0.05680(2) 0.17340(2) 0.01640(9) Uani 1 1 d . . . . .
Br1 Br 0.68593(3) 0.16312(3) 0.49268(2) 0.02114(10) Uani 1 1 d . . . . .
O1 O 0.9701(2) 0.28571(18) 0.95099(16) 0.0174(3) Uani 1 1 d . . . . .
O2 O 0.8735(2) 0.55338(19) 0.35979(17) 0.0196(4) Uani 1 1 d . . . . .
N4 N 0.3365(2) 0.4423(2) 0.12265(17) 0.0134(4) Uani 1 1 d . . . . .
N2 N 0.9046(2) -0.1891(2) 0.66215(18) 0.0154(4) Uani 1 1 d . . . . .
N3 N 0.2314(2) 0.2781(2) 0.03329(17) 0.0146(4) Uani 1 1 d . . . . .
N1 N 0.7982(2) -0.2583(2) 0.51225(18) 0.0174(4) Uani 1 1 d . . . . .
C17 C 0.8148(3) 0.4166(2) 0.2302(2) 0.0142(4) Uani 1 1 d . . . . .
H17 H 0.916824 0.391987 0.210257 0.017 Uiso 1 1 calc R . . . .
C18 C 0.7670(3) 0.5082(2) 0.3111(2) 0.0141(4) Uani 1 1 d . . . . .
C16 C 0.7108(2) 0.3626(2) 0.17989(19) 0.0124(4) Uani 1 1 d . . . . .
H16 H 0.743511 0.300882 0.126959 0.015 Uiso 1 1 calc R . . . .
C5 C 0.8791(2) 0.0399(2) 0.7179(2) 0.0126(4) Uani 1 1 d . . . . .
C12 C 0.3356(3) 0.1817(2) 0.0629(2) 0.0138(4) Uani 1 1 d . . . . .
H12 H 0.336183 0.092073 0.042742 0.017 Uiso 1 1 calc R . . . .
C3 C 0.8462(2) -0.0552(2) 0.64113(19) 0.0125(4) Uani 1 1 d . . . . .
C14 C 0.4458(2) 0.3480(2) 0.14992(19) 0.0118(4) Uani 1 1 d . . . . .
C11 C 0.2357(2) 0.4031(2) 0.0683(2) 0.0136(4) Uani 1 1 d . . . . .
H11 H 0.160066 0.469286 0.052834 0.016 Uiso 1 1 calc R . . . .
C8 C 0.9443(2) 0.2033(2) 0.87584(19) 0.0127(4) Uani 1 1 d . . . . .
C15 C 0.5571(2) 0.3993(2) 0.20717(19) 0.0119(4) Uani 1 1 d . . . . .
C13 C 0.4430(2) 0.2113(2) 0.1228(2) 0.0126(4) Uani 1 1 d . . . . .
C4 C 0.7619(3) -0.0207(2) 0.5502(2) 0.0143(4) Uani 1 1 d . . . . .
C6 C 1.0063(2) 0.0089(2) 0.7696(2) 0.0131(4) Uani 1 1 d . . . . .
H6 H 1.069400 -0.067049 0.751754 0.016 Uiso 1 1 calc R . . . .
C19 C 0.6140(3) 0.5469(2) 0.3387(2) 0.0168(4) Uani 1 1 d . . . . .
H19 H 0.581460 0.607853 0.392360 0.020 Uiso 1 1 calc R . . . .
C7 C 1.0390(2) 0.0902(2) 0.8469(2) 0.0146(4) Uani 1 1 d . . . . .
H7 H 1.124332 0.069153 0.879624 0.017 Uiso 1 1 calc R . . . .
C1 C 0.7402(3) -0.1265(3) 0.4900(2) 0.0172(4) Uani 1 1 d . . . . .
H1A H 0.682548 -0.104576 0.431434 0.021 Uiso 1 1 calc R . . . .
C10 C 0.7842(2) 0.1530(2) 0.7493(2) 0.0148(4) Uani 1 1 d . . . . .
H10 H 0.698912 0.174629 0.716698 0.018 Uiso 1 1 calc R . . . .
C20 C 0.5105(3) 0.4941(2) 0.2858(2) 0.0153(4) Uani 1 1 d . . . . .
H20 H 0.409346 0.522057 0.302894 0.018 Uiso 1 1 calc R . . . .
C2 C 0.8807(3) -0.2819(3) 0.5974(2) 0.0177(5) Uani 1 1 d . . . . .
H2A H 0.925535 -0.371939 0.612449 0.021 Uiso 1 1 calc R . . . .
C9 C 0.8154(3) 0.2329(2) 0.8278(2) 0.0150(4) Uani 1 1 d . . . . .
H9 H 0.750285 0.306409 0.848613 0.018 Uiso 1 1 calc R . . . .
H1 H 1.047(4) 0.269(4) 0.963(3) 0.033(10) Uiso 1 1 d . . . . .
H2 H 0.839(4) 0.603(4) 0.400(4) 0.034(10) Uiso 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
Br2 C13 1.899(2) . ?
Br1 C4 1.889(2) . ?
O1 C8 1.352(3) . ?
O2 C18 1.348(3) . ?
N4 C14 1.350(3) . ?
N4 C11 1.325(3) . ?
N2 C3 1.351(3) . ?
N2 C2 1.327(3) . ?
N3 C12 1.335(3) . ?
N3 C11 1.341(3) . ?
N1 C1 1.332(3) . ?
N1 C2 1.343(3) . ?
C17 C18 1.399(3) . ?
C17 C16 1.381(3) . ?
C18 C19 1.397(3) . ?
C16 C15 1.398(3) . ?
C5 C3 1.479(3) . ?
C5 C6 1.406(3) . ?
C5 C10 1.403(3) . ?
C12 C13 1.385(3) . ?
C3 C4 1.410(3) . ?
C14 C15 1.475(3) . ?
C14 C13 1.403(3) . ?
C8 C7 1.395(3) . ?
C8 C9 1.395(3) . ?
C15 C20 1.402(3) . ?
C4 C1 1.385(3) . ?
C6 C7 1.387(3) . ?
C19 C20 1.392(3) . ?
C10 C9 1.385(3) . ?

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
C11 N4 C14 118.59(19) . . ?
C2 N2 C3 119.2(2) . . ?
C12 N3 C11 115.44(19) . . ?
C1 N1 C2 115.2(2) . . ?
C16 C17 C18 120.1(2) . . ?
O2 C18 C17 117.0(2) . . ?
O2 C18 C19 123.4(2) . . ?
C19 C18 C17 119.6(2) . . ?
C17 C16 C15 121.1(2) . . ?
C6 C5 C3 118.22(19) . . ?
C10 C5 C3 123.59(19) . . ?
C10 C5 C6 118.0(2) . . ?
N3 C12 C13 121.8(2) . . ?
N2 C3 C5 115.09(19) . . ?
N2 C3 C4 117.8(2) . . ?
C4 C3 C5 127.1(2) . . ?
N4 C14 C15 116.05(19) . . ?
N4 C14 C13 117.9(2) . . ?
C13 C14 C15 126.08(19) . . ?
N4 C11 N3 126.8(2) . . ?
O1 C8 C7 122.8(2) . . ?
O1 C8 C9 117.6(2) . . ?
C9 C8 C7 119.6(2) . . ?
C16 C15 C14 121.81(19) . . ?
C16 C15 C20 118.5(2) . . ?
C20 C15 C14 119.58(19) . . ?
C12 C13 Br2 116.76(16) . . ?
C12 C13 C14 119.3(2) . . ?
C14 C13 Br2 123.80(16) . . ?
C3 C4 Br1 125.92(17) . . ?
C1 C4 Br1 115.44(17) . . ?
C1 C4 C3 118.5(2) . . ?
C7 C6 C5 120.9(2) . . ?
C20 C19 C18 119.9(2) . . ?
C6 C7 C8 120.2(2) . . ?
N1 C1 C4 123.0(2) . . ?
C9 C10 C5 121.2(2) . . ?
C19 C20 C15 120.7(2) . . ?
N2 C2 N1 126.3(2) . . ?
C10 C9 C8 120.1(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N3 0.75(4) 2.03(4) 2.734(3) 159(4) 1_656 yes
O2 H2 N1 0.74(4) 2.02(4) 2.737(3) 166(4) 1_565 yes

_olex2_date_sample_data_collection 2019-10-30
_olex2_exptl_crystal_mounting_method 
'Mounted on the glass stick by acrylic glue'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.974
_oxdiff_exptl_absorpt_empirical_full_min 0.654
