# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_hs-201-1
_database_code_depnum_ccdc_archive 'CCDC 2023439'
loop_
_audit_author_name
_audit_author_address
'Yibiao Li'
;wuyi University
China
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2020-10-20 downloaded from the CCDC.
;
_audit_creation_date             2018-08-14
_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         'C7 H7 Br N2 O'
_chemical_formula_sum            'C7 H7 Br N2 O'
_chemical_formula_weight         215.06
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   3.8839(6)
_cell_length_b                   8.7474(9)
_cell_length_c                   22.6670(14)
_cell_angle_alpha                81.742(8)
_cell_angle_beta                 88.786(9)
_cell_angle_gamma                85.859(10)
_cell_volume                     760.07(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2534
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3760
_cell_measurement_theta_min      5.1030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4416
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.119
_diffrn_reflns_theta_min         1.970
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  27.00   1.00    1.00    --  -40.73  38.00  90.00   92
  2  ω    -47.00  -2.00   1.00    1.00    --  -40.73 125.00 150.00   45
  3  ω   -112.00 -16.00   1.00    1.00    --  -40.73 -38.00 -90.00   96
  4  ω      1.00  33.00   1.00    1.00    --   40.73 -99.00 150.00   32
  5  ω     30.00 102.00   1.00    1.00    --  106.95 -95.00  30.00   72
  6  ω     74.00 106.00   1.00    1.00    --  106.95-111.00 -30.00   32
  7  ω     82.00 109.00   1.00    1.00    --  106.95-111.00-150.00   27
  8  ω     49.00  96.00   1.00    1.00    --   40.73-125.00 -60.00   47
  9  ω     34.00  75.00   1.00    1.00    --  106.95-111.00-150.00   41
 10  ω     36.00 136.00   1.00    1.00    --  106.95 -61.00-150.00  100
 11  ω     63.00 177.00   1.00    1.00    --  106.95  15.00   0.00  114
 12  ω    123.00 150.00   1.00    1.00    --  106.95 107.00 125.00   27
 13  ω    105.00 141.00   1.00    1.00    --  106.95 111.00   0.00   36
 14  ω    113.00 151.00   1.00    1.00    --  106.95 178.00 -60.00   38
 15  ω     84.00 111.00   1.00    1.00    --  106.95 178.00 -60.00   27
 16  ω     85.00 171.00   1.00    1.00    --  106.95  45.00  60.00   86
 17  ω     37.00 122.00   1.00    1.00    --  106.95 -45.00  30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1142516000
_diffrn_orient_matrix_UB_12      0.1609892000
_diffrn_orient_matrix_UB_13      0.0164762000
_diffrn_orient_matrix_UB_21      0.1308188000
_diffrn_orient_matrix_UB_22      -0.0520381000
_diffrn_orient_matrix_UB_23      0.0639263000
_diffrn_orient_matrix_UB_31      0.3577890000
_diffrn_orient_matrix_UB_32      0.0565732000
_diffrn_orient_matrix_UB_33      -0.0189492000
_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                2649
_reflns_number_total             2924
_reflns_odcompleteness_completeness 99.38
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         1.546
_refine_diff_density_min         -1.059
_refine_diff_density_rms         0.220
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.071
_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)+(0.0997P)²+8.9635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.1915
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N006(H006), C4(H4), C1(H1A), C2(H2), C00J(H00J), C00L(H00L), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C00G(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.85376(18) 0.23144(8) -0.03651(3) 0.0189(3) Uani 1 1 d . . . . .
Br02 Br 0.14408(18) 0.74738(8) 0.53667(3) 0.0195(3) Uani 1 1 d . . . . .
O003 O 0.9286(13) 0.9837(5) 0.2616(2) 0.0208(10) Uani 1 1 d . . . . .
O1 O 0.4650(13) 0.4830(5) 0.2366(2) 0.0198(10) Uani 1 1 d . . . . .
N1 N 0.3118(15) 0.2549(6) 0.2123(2) 0.0173(12) Uani 1 1 d . . . . .
H1 H 0.204554 0.173933 0.225340 0.021 Uiso 1 1 calc R . . . .
N006 N 0.6772(16) 0.7560(6) 0.2863(2) 0.0197(13) Uani 1 1 d . . . . .
H006 H 0.634008 0.672522 0.272792 0.024 Uiso 1 1 calc R . . . .
N5 N 0.4299(15) 0.1297(6) 0.1311(3) 0.0182(12) Uani 1 1 d . . . . .
N008 N 0.4573(16) 0.6339(7) 0.3731(3) 0.0190(12) Uani 1 1 d . . . . .
C009 C 0.3197(16) 0.7611(8) 0.4573(3) 0.0135(12) Uani 1 1 d . . . . .
C00A C 0.8470(18) 0.8603(7) 0.2481(3) 0.0178(13) Uani 1 1 d . . . . .
C4 C 0.5469(18) 0.1249(8) 0.0761(3) 0.0175(13) Uani 1 1 d . . . . .
H4 H 0.534486 0.033931 0.059705 0.021 Uiso 1 1 calc R . . . .
C8 C 0.1753(19) 0.3164(8) 0.3113(3) 0.0215(14) Uani 1 1 d . . . . .
H8A H 0.352373 0.305882 0.340786 0.032 Uiso 1 1 calc GR . . . .
H8B H 0.071208 0.219738 0.312531 0.032 Uiso 1 1 calc GR . . . .
H8C H 0.002733 0.395227 0.319294 0.032 Uiso 1 1 calc GR . . . .
C7 C 0.3316(18) 0.3610(7) 0.2504(3) 0.0176(13) Uani 1 1 d . . . . .
C1 C 0.5845(19) 0.3944(8) 0.1225(3) 0.0199(14) Uani 1 1 d . . . . .
H1A H 0.594455 0.484458 0.139650 0.024 Uiso 1 1 calc R . . . .
C2 C 0.7041(18) 0.3868(8) 0.0656(3) 0.0203(14) Uani 1 1 d . . . . .
H2 H 0.795284 0.472189 0.043056 0.024 Uiso 1 1 calc R . . . .
C00G C 0.9298(19) 0.8099(8) 0.1882(3) 0.0202(14) Uani 1 1 d . . . . .
H00A H 0.719464 0.805818 0.167173 0.030 Uiso 1 1 calc GR . . . .
H00B H 1.050064 0.709123 0.193794 0.030 Uiso 1 1 calc GR . . . .
H00C H 1.072680 0.882558 0.165521 0.030 Uiso 1 1 calc GR . . . .
C6 C 0.4478(18) 0.2635(7) 0.1540(3) 0.0175(14) Uani 1 1 d . . . . .
C00I C 0.5635(18) 0.7664(7) 0.3447(3) 0.0169(13) Uani 1 1 d . . . . .
C00J C 0.3405(19) 0.6309(8) 0.4286(3) 0.0213(14) Uani 1 1 d . . . . .
H00J H 0.269889 0.538279 0.448979 0.026 Uiso 1 1 calc R . . . .
C3 C 0.6865(17) 0.2496(8) 0.0422(3) 0.0149(13) Uani 1 1 d . . . . .
C00L C 0.4325(19) 0.8982(8) 0.4280(3) 0.0199(14) Uani 1 1 d . . . . .
H00L H 0.422737 0.986618 0.446624 0.024 Uiso 1 1 calc R . . . .
C00M C 0.5598(18) 0.9014(8) 0.3707(3) 0.0182(14) Uani 1 1 d . . . . .
H00M H 0.641111 0.991390 0.349905 0.022 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 C3 1.909(6) . ?
Br02 C009 1.900(6) . ?
O003 C00A 1.228(8) . ?
O1 C7 1.217(8) . ?
N1 C7 1.362(8) . ?
N1 C6 1.407(9) . ?
N006 C00A 1.361(9) . ?
N006 C00I 1.399(9) . ?
N5 C4 1.323(9) . ?
N5 C6 1.354(9) . ?
N008 C00I 1.331(9) . ?
N008 C00J 1.325(9) . ?
C009 C00J 1.388(10) . ?
C009 C00L 1.380(10) . ?
C00A C00G 1.509(9) . ?
C4 C3 1.380(10) . ?
C8 C7 1.506(9) . ?
C1 C2 1.372(10) . ?
C1 C6 1.393(10) . ?
C2 C3 1.387(9) . ?
C00I C00M 1.393(9) . ?
C00L C00M 1.378(10) . ?

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
C7 N1 C6 127.0(6) . . ?
C00A N006 C00I 128.7(6) . . ?
C4 N5 C6 117.8(6) . . ?
C00J N008 C00I 118.3(6) . . ?
C00J C009 Br02 119.7(5) . . ?
C00L C009 Br02 121.0(5) . . ?
C00L C009 C00J 119.3(6) . . ?
O003 C00A N006 122.8(6) . . ?
O003 C00A C00G 123.1(6) . . ?
N006 C00A C00G 114.1(6) . . ?
N5 C4 C3 122.5(6) . . ?
O1 C7 N1 122.9(6) . . ?
O1 C7 C8 122.1(6) . . ?
N1 C7 C8 115.0(6) . . ?
C2 C1 C6 118.1(6) . . ?
C1 C2 C3 118.9(6) . . ?
N5 C6 N1 112.5(6) . . ?
N5 C6 C1 123.0(6) . . ?
C1 C6 N1 124.4(6) . . ?
N008 C00I N006 113.2(6) . . ?
N008 C00I C00M 123.1(7) . . ?
C00M C00I N006 123.7(6) . . ?
N008 C00J C009 122.4(6) . . ?
C4 C3 Br1 119.7(5) . . ?
C4 C3 C2 119.6(6) . . ?
C2 C3 Br1 120.7(5) . . ?
C00M C00L C009 118.6(6) . . ?
C00L C00M C00I 118.3(6) . . ?


_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.348
_oxdiff_exptl_absorpt_empirical_full_min 0.601
