# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ga_81211a_a
_database_code_depnum_ccdc_archive 'CCDC 1911103'
loop_
_audit_author_name
_audit_author_address
'Hui Liu'
;Jiaxing University
China
;
_audit_update_record             
;
2019-04-19 deposited with the CCDC.	2019-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 Br2 N O2'
_chemical_formula_weight         425.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5896(8)
_cell_length_b                   10.9767(11)
_cell_length_c                   11.9609(13)
_cell_angle_alpha                110.338(4)
_cell_angle_beta                 100.049(4)
_cell_angle_gamma                106.048(4)
_cell_volume                     856.48(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5946
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      56.93

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    4.006
_shelx_estimated_absorpt_T_min   0.434
_shelx_estimated_absorpt_T_max   0.532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.496
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9260
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.524
_diffrn_reflns_theta_max         55.490
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3263
_reflns_number_gt                2762
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+0.6277P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3263
_refine_ls_number_parameters     207
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.73426(6) 0.49886(4) 0.43228(5) 0.0819(2) Uani 1 1 d . . . . .
Br2 Br 1.03197(8) 0.66739(7) 0.85443(5) 0.1189(3) Uani 1 1 d . . . . .
N1 N 0.3428(3) 0.1460(3) 0.5007(3) 0.0497(6) Uani 1 1 d D . . . .
H1' H 0.448(3) 0.159(3) 0.544(2) 0.038(8) Uiso 1 1 d D . . . .
O1 O 0.7104(3) 0.1638(3) 0.5165(2) 0.0593(6) Uani 1 1 d D . . . .
H1 H 0.817(4) 0.160(5) 0.528(4) 0.093(15) Uiso 1 1 d D . . . .
O2 O 0.0559(4) 0.1623(3) 0.5078(3) 0.0791(8) Uani 1 1 d . . . . .
C1 C 0.4946(4) 0.1611(3) 0.3428(3) 0.0487(7) Uani 1 1 d . . . . .
C2 C 0.3273(4) 0.1175(3) 0.3737(3) 0.0496(7) Uani 1 1 d . . . . .
C3 C 0.1507(5) 0.0440(4) 0.2791(4) 0.0700(10) Uani 1 1 d . . . . .
H3 H 0.0382 0.0136 0.2989 0.084 Uiso 1 1 calc R U . . .
C4 C 0.1442(7) 0.0170(5) 0.1572(4) 0.0862(13) Uani 1 1 d . . . . .
H4 H 0.0265 -0.0309 0.0950 0.103 Uiso 1 1 calc R U . . .
C5 C 0.3057(8) 0.0588(5) 0.1264(4) 0.0854(12) Uani 1 1 d . . . . .
H5 H 0.2994 0.0389 0.0433 0.102 Uiso 1 1 calc R U . . .
C6 C 0.4805(6) 0.1311(4) 0.2185(3) 0.0686(9) Uani 1 1 d . . . . .
H6 H 0.5912 0.1604 0.1965 0.082 Uiso 1 1 calc R U . . .
C7 C 0.6909(4) 0.2372(3) 0.4411(3) 0.0481(7) Uani 1 1 d . . . . .
H7 H 0.7894 0.2368 0.3979 0.058 Uiso 1 1 calc R U . . .
C8 C 0.7245(4) 0.3873(3) 0.5221(3) 0.0518(7) Uani 1 1 d . . . . .
C9 C 0.7518(5) 0.4405(4) 0.6435(4) 0.0699(10) Uani 1 1 d . . . . .
H9 H 0.7481 0.3804 0.6827 0.084 Uiso 1 1 calc R U . . .
C10 C 0.7883(7) 0.5894(6) 0.7240(5) 0.1040(18) Uani 1 1 d . . . . .
H10A H 0.6854 0.5946 0.7613 0.125 Uiso 1 1 calc R U . . .
H10B H 0.7922 0.6424 0.6738 0.125 Uiso 1 1 calc R U . . .
C11 C 0.2150(4) 0.1702(3) 0.5610(3) 0.0544(8) Uani 1 1 d . . . . .
C12 C 0.2826(5) 0.2130(3) 0.6981(4) 0.0606(8) Uani 1 1 d . . . . .
C13 C 0.4200(7) 0.1737(5) 0.7540(4) 0.0769(11) Uani 1 1 d . . . . .
H13 H 0.4740 0.1174 0.7050 0.092 Uiso 1 1 calc R U . . .
C14 C 0.4765(10) 0.2176(6) 0.8815(5) 0.1068(17) Uani 1 1 d . . . . .
H14 H 0.5684 0.1914 0.9192 0.128 Uiso 1 1 calc R U . . .
C15 C 0.3949(13) 0.3012(7) 0.9528(6) 0.119(2) Uani 1 1 d . . . . .
H15 H 0.4330 0.3317 1.0391 0.143 Uiso 1 1 calc R U . . .
C16 C 0.2588(11) 0.3400(6) 0.8982(6) 0.115(2) Uani 1 1 d . . . . .
H16 H 0.2056 0.3967 0.9476 0.137 Uiso 1 1 calc R U . . .
C17 C 0.2016(7) 0.2959(5) 0.7728(5) 0.0851(13) Uani 1 1 d . . . . .
H17 H 0.1075 0.3212 0.7361 0.102 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 C8 1.884(3) . ?
Br2 C10 1.943(5) . ?
N1 C11 1.336(4) . ?
N1 C2 1.417(4) . ?
N1 H1' 0.820(18) . ?
O1 C7 1.418(4) . ?
O1 H1 0.810(19) . ?
O2 C11 1.227(4) . ?
C1 C6 1.385(5) . ?
C1 C2 1.389(4) . ?
C1 C7 1.522(4) . ?
C2 C3 1.402(5) . ?
C3 C4 1.371(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.347(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.514(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.316(5) . ?
C9 C10 1.495(6) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.487(5) . ?
C12 C13 1.388(6) . ?
C12 C17 1.393(5) . ?
C13 C14 1.374(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.351(8) . ?
C16 H16 0.9300 . ?
C17 H17 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
C11 N1 C2 127.9(3) . . ?
C11 N1 H1' 116(2) . . ?
C2 N1 H1' 115(2) . . ?
C7 O1 H1 109(4) . . ?
C6 C1 C2 118.3(3) . . ?
C6 C1 C7 119.8(3) . . ?
C2 C1 C7 121.8(3) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 N1 118.1(3) . . ?
C3 C2 N1 122.2(3) . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 121.4(4) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O1 C7 C8 110.1(3) . . ?
O1 C7 C1 109.2(2) . . ?
C8 C7 C1 112.9(2) . . ?
O1 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
C1 C7 H7 108.2 . . ?
C9 C8 C7 125.6(3) . . ?
C9 C8 Br1 121.4(3) . . ?
C7 C8 Br1 113.0(2) . . ?
C8 C9 C10 125.6(5) . . ?
C8 C9 H9 117.2 . . ?
C10 C9 H9 117.2 . . ?
C9 C10 Br2 109.2(3) . . ?
C9 C10 H10A 109.8 . . ?
Br2 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
Br2 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
O2 C11 N1 122.5(3) . . ?
O2 C11 C12 122.4(3) . . ?
N1 C11 C12 115.1(3) . . ?
C13 C12 C17 119.1(4) . . ?
C13 C12 C11 123.3(3) . . ?
C17 C12 C11 117.6(4) . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.1(6) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 121.0(5) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 120.1(5) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 120.5(5) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?

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
C6 C1 C2 C3 0.6(5) . . . . ?
C7 C1 C2 C3 -178.0(3) . . . . ?
C6 C1 C2 N1 178.8(3) . . . . ?
C7 C1 C2 N1 0.2(4) . . . . ?
C11 N1 C2 C1 149.0(3) . . . . ?
C11 N1 C2 C3 -32.9(5) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
N1 C2 C3 C4 -178.8(4) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C3 C4 C5 C6 -0.7(8) . . . . ?
C4 C5 C6 C1 0.6(7) . . . . ?
C2 C1 C6 C5 -0.6(6) . . . . ?
C7 C1 C6 C5 178.1(4) . . . . ?
C6 C1 C7 O1 -130.3(3) . . . . ?
C2 C1 C7 O1 48.3(4) . . . . ?
C6 C1 C7 C8 106.9(3) . . . . ?
C2 C1 C7 C8 -74.5(4) . . . . ?
O1 C7 C8 C9 -5.3(4) . . . . ?
C1 C7 C8 C9 117.0(3) . . . . ?
O1 C7 C8 Br1 172.31(18) . . . . ?
C1 C7 C8 Br1 -65.4(3) . . . . ?
C7 C8 C9 C10 178.9(3) . . . . ?
Br1 C8 C9 C10 1.5(5) . . . . ?
C8 C9 C10 Br2 -121.9(4) . . . . ?
C2 N1 C11 O2 4.4(5) . . . . ?
C2 N1 C11 C12 -173.3(3) . . . . ?
O2 C11 C12 C13 154.3(4) . . . . ?
N1 C11 C12 C13 -28.0(5) . . . . ?
O2 C11 C12 C17 -25.3(5) . . . . ?
N1 C11 C12 C17 152.4(3) . . . . ?
C17 C12 C13 C14 -0.7(7) . . . . ?
C11 C12 C13 C14 179.6(4) . . . . ?
C12 C13 C14 C15 -0.1(8) . . . . ?
C13 C14 C15 C16 0.3(10) . . . . ?
C14 C15 C16 C17 0.3(10) . . . . ?
C15 C16 C17 C12 -1.1(9) . . . . ?
C13 C12 C17 C16 1.3(7) . . . . ?
C11 C12 C17 C16 -179.0(4) . . . . ?

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
O1 H1 O2 0.810(19) 1.87(2) 2.647(3) 161(5) 1_655
N1 H1' O1 0.820(18) 2.06(2) 2.710(3) 136(3) .

_refine_diff_density_max         0.576
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.059



