# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2000863'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Qingdao University of Science and Technology
China
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_audit_creation_date             2019-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 Br N3'
_chemical_formula_sum            'C13 H10 Br N3'
_chemical_formula_weight         288.15
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'c h n Br'
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'

_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                   13.7045(3)
_cell_length_b                   4.14060(10)
_cell_length_c                   20.5390(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.208(2)
_cell_angle_gamma                90
_cell_volume                     1160.67(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3310
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.2470
_cell_measurement_theta_min      3.7330
_shelx_estimated_absorpt_T_max   0.456
_shelx_estimated_absorpt_T_min   0.456
_exptl_absorpt_coefficient_mu    4.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5424
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.026
_diffrn_reflns_theta_max         67.026
_diffrn_reflns_theta_min         3.727
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_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    -38.00  35.00   0.50    0.05    --   37.97 -57.00   0.00  146
  2  ω     44.00  69.00   0.50    0.05    --   37.97-129.00 132.00   50
  3  ω     86.00 120.00   0.50    0.06    --  112.45-129.00 132.00   68
  4  ω     39.00 106.00   0.50    0.06    --  112.45 -94.00 -30.00  134
  5  ω     92.00 123.00   0.50    0.06    --  112.45-140.00 -40.00   62
  6  ω     52.00  80.00   0.50    0.06    --  112.45 -94.00-180.00   56
  7  ω    145.00 173.00   0.50    0.06    --  112.45  45.00 -60.00   56
  8  ω    105.00 147.00   0.50    0.06    --  112.45 129.00-154.00   84
  9  ω     79.00 119.00   0.50    0.06    --  112.45  45.00 -60.00   80
 10  ω     29.00  55.00   0.50    0.06    --  112.45 -94.00  60.00   52
 11  ω   -103.00 -68.00   0.50    0.05    --  -37.97-129.00 132.00   70
 12  ω   -109.00 -65.00   0.50    0.05    --  -37.97 -57.00  30.00   88
 13  ω    -51.00  -9.00   0.50    0.05    --  -37.97 -57.00  30.00   84
 14  ω   -111.00 -61.00   0.50    0.05    --  -37.97-140.00 -40.00  100
 15  ω   -151.00 -60.00   0.50    0.06    --  -98.50-140.00 -40.00  182
 16  ω   -166.00 -84.00   0.50    0.06    --  -98.50-129.00 132.00  164
 17  ω   -168.00 -86.00   0.50    0.06    --  -98.50 -94.00  60.00  164
 18  ω   -172.00 -80.00   0.50    0.06    --  -98.50 -94.00-120.00  184
 19  ω    -81.00 -17.00   0.50    0.06    --  -98.50 111.00   0.00  128
 20  ω    -92.00 -29.00   0.50    0.05    --  -37.97 129.00-154.00  126
 21  ω    -82.00 -57.00   0.50    0.06    --  -98.50 129.00-154.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0199233000
_diffrn_orient_matrix_UB_12      0.3649538000
_diffrn_orient_matrix_UB_13      0.0075769000
_diffrn_orient_matrix_UB_21      0.1075633000
_diffrn_orient_matrix_UB_22      -0.0711000000
_diffrn_orient_matrix_UB_23      0.0241792000
_diffrn_orient_matrix_UB_31      0.0279443000
_diffrn_orient_matrix_UB_32      0.0145368000
_diffrn_orient_matrix_UB_33      -0.0709003000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1918
_reflns_number_total             2051
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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         0.530
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.050
_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)+(0.0728P)²+0.5134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1103
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.92953(2) 0.29009(9) 0.75846(2) 0.05088(18) Uani 1 1 d . . . . .
N1 N 0.72298(19) 0.7453(6) 0.50592(12) 0.0420(6) Uani 1 1 d . . . . .
N2 N 0.62706(17) 0.6541(6) 0.51367(12) 0.0423(5) Uani 1 1 d . . . . .
N3 N 0.54552(16) 0.3987(8) 0.59547(11) 0.0503(6) Uani 1 1 d . . . . .
H3A H 0.560377 0.279215 0.629341 0.060 Uiso 1 1 d GR . . . .
H3B H 0.511316 0.561189 0.606649 0.060 Uiso 1 1 d GR . . . .
C1 C 0.86773(18) 0.4396(7) 0.67756(12) 0.0405(6) Uani 1 1 d . . . . .
C2 C 0.92526(19) 0.6022(8) 0.63455(14) 0.0441(6) Uani 1 1 d . . . . .
H2 H 0.991467 0.636182 0.646808 0.053 Uiso 1 1 calc R . . . .
C3 C 0.8856(2) 0.7109(7) 0.57515(16) 0.0451(7) Uani 1 1 d . . . . .
H3 H 0.923856 0.816640 0.546619 0.054 Uiso 1 1 calc R . . . .
C4 C 0.78460(19) 0.6574(7) 0.55850(13) 0.0383(6) Uani 1 1 d . . . . .
C5 C 0.72756(17) 0.5031(7) 0.60247(12) 0.0375(5) Uani 1 1 d . . . . .
C6 C 0.76917(18) 0.3879(8) 0.66294(12) 0.0409(6) Uani 1 1 d . . . . .
H6 H 0.731747 0.281429 0.691831 0.049 Uiso 1 1 calc R . . . .
C7 C 0.63012(17) 0.5105(7) 0.57117(12) 0.0400(6) Uani 1 1 d . . . . .
C8 C 0.74413(19) 0.8746(7) 0.44465(13) 0.0391(6) Uani 1 1 d . . . . .
C9 C 0.6749(2) 1.0663(8) 0.40947(13) 0.0458(6) Uani 1 1 d . . . . .
H9 H 0.616016 1.114943 0.426510 0.055 Uiso 1 1 calc R . . . .
C10 C 0.6940(3) 1.1847(8) 0.34882(16) 0.0531(8) Uani 1 1 d . . . . .
H10 H 0.647541 1.311516 0.324940 0.064 Uiso 1 1 calc R . . . .
C11 C 0.7822(3) 1.1149(8) 0.32352(15) 0.0548(8) Uani 1 1 d . . . . .
H11 H 0.794977 1.195681 0.282901 0.066 Uiso 1 1 calc R . . . .
C12 C 0.8505(2) 0.9264(8) 0.35870(15) 0.0507(7) Uani 1 1 d . . . . .
H12 H 0.909535 0.880358 0.341679 0.061 Uiso 1 1 calc R . . . .
C13 C 0.8326(2) 0.8038(7) 0.41916(16) 0.0453(7) Uani 1 1 d . . . . .
H13 H 0.879073 0.675351 0.442579 0.054 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 C1 1.899(3) . ?
N1 N2 1.391(4) . ?
N1 C4 1.359(4) . ?
N1 C8 1.421(4) . ?
N2 C7 1.320(4) . ?
N3 H3A 0.8628 . ?
N3 H3B 0.8629 . ?
N3 C7 1.383(3) . ?
C1 C2 1.408(4) . ?
C1 C6 1.373(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.413(4) . ?
C4 C5 1.401(4) . ?
C5 C6 1.403(4) . ?
C5 C7 1.429(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.389(4) . ?
C8 C13 1.394(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(4) . ?
C13 H13 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
N2 N1 C8 118.3(3) . . ?
C4 N1 N2 111.2(2) . . ?
C4 N1 C8 130.0(2) . . ?
C7 N2 N1 105.7(2) . . ?
H3A N3 H3B 109.1 . . ?
C7 N3 H3A 109.8 . . ?
C7 N3 H3B 109.2 . . ?
C2 C1 Br1 118.31(19) . . ?
C6 C1 Br1 119.5(2) . . ?
C6 C1 C2 122.2(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.8(3) . . ?
C4 C3 H3 121.1 . . ?
N1 C4 C3 132.4(3) . . ?
N1 C4 C5 107.0(2) . . ?
C5 C4 C3 120.5(3) . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 C7 104.7(2) . . ?
C6 C5 C7 133.9(2) . . ?
C1 C6 C5 117.0(2) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
N2 C7 N3 120.9(2) . . ?
N2 C7 C5 111.4(2) . . ?
N3 C7 C5 127.6(2) . . ?
C9 C8 N1 119.4(2) . . ?
C9 C8 C13 120.1(3) . . ?
C13 C8 N1 120.5(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 H13 120.3 . . ?
C12 C13 C8 119.4(3) . . ?
C12 C13 H13 120.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.269
_oxdiff_exptl_absorpt_empirical_full_min 0.536
