# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

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

data_exp_459
_database_code_depnum_ccdc_archive 'CCDC 1915404'
loop_
_audit_author_name
_audit_author_address
'oxyhalogenation eight'
;East China Normal University
China
;
_audit_update_record             
;
2019-05-11 deposited with the CCDC.	2019-10-21 downloaded from the CCDC.
;
_audit_creation_date             2018-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H5 Br2 N O'
_chemical_formula_sum            'C9 H5 Br2 N O'
_chemical_formula_weight         302.96
_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      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                   8.40930(10)
_cell_length_b                   9.09290(10)
_cell_length_c                   13.3012(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.1410(10)
_cell_angle_gamma                90
_cell_volume                     986.26(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14654
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1730
_cell_measurement_theta_min      4.8700
_shelx_estimated_absorpt_T_max   0.101
_shelx_estimated_absorpt_T_min   0.090
_exptl_absorpt_coefficient_mu    10.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    2.040
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.42
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1818
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19779
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.029
_diffrn_reflns_theta_max         67.029
_diffrn_reflns_theta_min         5.666
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  79.00   1.00    1.00    --    0.00  82.00-120.00   60
  2  ω    -16.00  15.00   1.00    1.00    --    0.00  38.00  30.00   31
  3  ω     38.00  88.00   1.00    1.00    --    0.00  38.00 -30.00   50
  4  ω    -32.00  10.00   1.00    1.00    --    0.00  82.00-120.00   42
  5  ω    -32.00   1.00   1.00    1.00    --    0.00  82.00  30.00   33
  6  ω    -11.00  23.00   1.00    1.00    --    0.00  38.00-180.00   34
  7  ω     37.00  88.00   1.00    1.00    --    0.00  57.00-150.00   51
  8  ω     45.00  82.00   1.00    1.00    --    0.00  38.00 150.00   37
  9  ω     48.00  73.00   1.00    1.00    --    0.00  38.00-180.00   25
 10  ω     24.00  88.00   1.00    1.00    --    0.00  38.00  30.00   64
 11  ω     29.00  78.00   1.00    1.00    --    0.00  82.00  30.00   49
 12  ω     -8.00  18.00   1.00    1.00    --    0.00  57.00-150.00   26
 13  ω    -18.00  14.00   1.00    1.00    --    0.00  38.00 150.00   32
 14  ω    -19.00  15.00   1.00    1.00    --    0.00  38.00 -30.00   34
 15  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 16  ω    100.00 126.00   1.00    1.00    --   95.80 -82.00   0.00   26
 17  ω    115.00 141.00   1.00    1.00    --   95.80  80.00  18.21   26
 18  ω     52.00  96.00   1.00    1.00    --   95.80 -82.00   0.00   44
 19  ω     18.00  44.00   1.00    1.00    --   95.80 -82.00   0.00   26
 20  ω     64.00  90.00   1.00    1.00    --   95.80  80.00  18.21   26
 21  ω     69.00 135.00   1.00    1.00    --   95.80  67.00 -21.15   66
 22  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 23  ω     66.00  92.00   1.00    1.00    --   95.80  77.00 120.00   26
 24  ω    109.00 135.00   1.00    1.00    --   95.80  77.00 120.00   26
 25  ω    129.00 184.00   1.00    1.00    --   95.80  61.00 -90.00   55
 26  ω      7.00  76.00   1.00    1.00    --   95.80 -61.00   0.00   69
 27  ω     63.00  92.00   1.00    1.00    --   95.80  82.00   0.00   29
 28  ω      8.00 127.00   1.00    1.00    --   95.80 -82.00 -60.00  119
 29  ω     71.00 119.00   1.00    1.00    --   95.80  61.00-180.00   48
 30  ω     63.00  95.00   1.00    1.00    --   95.80  82.00 -60.00   32
 31  ω     16.00 128.00   1.00    1.00    --   95.80 -82.00-150.00  112
 32  ω    113.00 139.00   1.00    1.00    --   95.80  77.00 -60.00   26
 33  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 34  ω    147.00 173.00   1.00    1.00    --   95.80  67.00   1.35   26
 35  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-120.00   26
 36  ω     74.00 128.00   1.00    1.00    --   95.80  61.00 150.00   54
 37  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 38  ω     64.00  90.00   1.00    1.00    --   95.80  82.00 -30.00   26
 39  ω     71.00 123.00   1.00    1.00    --   95.80  61.00-120.00   52
 40  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 41  ω     65.00  92.00   1.00    1.00    --   95.80  82.00-180.00   27
 42  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 43  ω    144.00 170.00   1.00    1.00    --   95.80  82.00  90.00   26
 44  ω    115.00 153.00   1.00    1.00    --   95.80  61.00 -60.00   38
 45  ω     76.00 169.00   1.00    1.00    --   95.80  30.00  60.00   93
 46  ω     75.00 100.00   1.00    1.00    --   95.80  45.00  60.00   25
 47  ω     75.00 135.00   1.00    1.00    --   95.80  45.00  90.00   60
 48  ω    143.00 169.00   1.00    1.00    --   95.80  45.00  90.00   26
 49  ω     75.00 185.00   1.00    1.00    --   95.80  45.00 150.00  110
 50  ω     71.00 108.00   1.00    1.00    --   95.80  61.00 -90.00   37
 51  ω     72.00 109.00   1.00    1.00    --   95.80  61.00 -60.00   37
 52  ω      6.00 113.00   1.00    1.00    --   95.80 -61.00-180.00  107
 53  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  30.00   25
 54  ω     88.00 113.00   1.00    1.00    --   95.80 -61.00   0.00   25
 55  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 56  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 57  ω    156.00 185.00   1.00    1.00    --   95.80  82.00 -90.00   29
 58  ω     79.00 183.00   1.00    1.00    --   95.80  45.00-120.00  104
 59  ω    145.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   40
 60  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  90.00   25
 61  ω     72.00 112.00   1.00    1.00    --   95.80  67.00   1.35   40
 62  ω     76.00 156.00   1.00    1.00    --   95.80  45.00-150.00   80
 63  ω     92.00 117.00   1.00    1.00    --   95.80  77.00 -92.81   25
 64  ω     74.00 100.00   1.00    1.00    --   95.80  61.00  90.00   26
 65  ω     65.00 120.00   1.00    1.00    --   95.80  77.00  90.00   55
 66  ω      6.00 107.00   1.00    1.00    --   95.80 -82.00  90.00  101
 67  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -92.81   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0988197000
_diffrn_orient_matrix_UB_12      -0.0765143000
_diffrn_orient_matrix_UB_13      -0.0989941000
_diffrn_orient_matrix_UB_21      0.0036302000
_diffrn_orient_matrix_UB_22      0.1424851000
_diffrn_orient_matrix_UB_23      -0.0619820000
_diffrn_orient_matrix_UB_31      0.1610597000
_diffrn_orient_matrix_UB_32      -0.0501808000
_diffrn_orient_matrix_UB_33      -0.0250860000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1666
_reflns_number_total             1733
_reflns_odcompleteness_completeness 99.95
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (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         0.792
_refine_diff_density_min         -1.425
_refine_diff_density_rms         0.161
_refine_ls_extinction_coef       0.0289(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.066
_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)+(0.0909P)²+0.2524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1280
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.26451(5) 0.49065(4) 0.10464(3) 0.0494(3) Uani 1 1 d . . . . .
Br2 Br -0.01898(5) 0.27014(5) 0.12488(4) 0.0553(3) Uani 1 1 d . . . . .
O1 O 0.2924(3) 0.0988(3) 0.14826(19) 0.0482(6) Uani 1 1 d . . . . .
N1 N 1.1033(5) 0.2963(5) 0.5005(4) 0.0772(13) Uani 1 1 d . . . . .
C1 C 0.6125(4) 0.1334(4) 0.2611(3) 0.0467(9) Uani 1 1 d . . . . .
H1 H 0.586670 0.053656 0.216313 0.056 Uiso 1 1 calc R . . . .
C2 C 0.7686(5) 0.1479(5) 0.3224(3) 0.0498(9) Uani 1 1 d . . . . .
H2 H 0.848551 0.078872 0.318685 0.060 Uiso 1 1 calc R . . . .
C3 C 0.8066(4) 0.2670(4) 0.3902(3) 0.0416(8) Uani 1 1 d . . . . .
C4 C 0.6887(4) 0.3698(4) 0.3959(3) 0.0454(8) Uani 1 1 d . . . . .
H4 H 0.714526 0.449202 0.440978 0.055 Uiso 1 1 calc R . . . .
C5 C 0.5312(4) 0.3539(4) 0.3338(3) 0.0431(8) Uani 1 1 d . . . . .
H5 H 0.450902 0.422290 0.338136 0.052 Uiso 1 1 calc R . . . .
C6 C 0.4924(4) 0.2368(4) 0.2654(3) 0.0361(7) Uani 1 1 d . . . . .
C7 C 0.3266(4) 0.2117(4) 0.1962(2) 0.0358(7) Uani 1 1 d . . . . .
C8 C 0.2008(4) 0.3351(4) 0.1873(2) 0.0380(7) Uani 1 1 d . . . . .
H8 H 0.204823 0.373330 0.256785 0.046 Uiso 1 1 calc R . . . .
C9 C 0.9718(5) 0.2838(5) 0.4529(4) 0.0549(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C8 1.946(3) . ?
Br2 C8 1.925(3) . ?
O1 C7 1.206(4) . ?
N1 C9 1.138(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(5) . ?
C1 C6 1.391(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(5) . ?
C3 C4 1.378(5) . ?
C3 C9 1.443(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(5) . ?
C6 C7 1.489(5) . ?
C7 C8 1.527(5) . ?
C8 H8 0.9800 . ?

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
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.6(3) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C9 119.4(4) . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 C9 120.1(3) . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 116.8(3) . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 C7 123.9(3) . . ?
O1 C7 C6 121.6(3) . . ?
O1 C7 C8 120.9(3) . . ?
C6 C7 C8 117.5(3) . . ?
Br1 C8 H8 108.9 . . ?
Br2 C8 Br1 110.31(15) . . ?
Br2 C8 H8 108.9 . . ?
C7 C8 Br1 107.3(2) . . ?
C7 C8 Br2 112.5(2) . . ?
C7 C8 H8 108.9 . . ?
N1 C9 C3 178.5(5) . . ?

_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 5.354
_oxdiff_exptl_absorpt_empirical_full_min 0.293
