# Electronic Supplementary Material (ESI) for ChemComm.
# 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_x_a
_database_code_depnum_ccdc_archive 'CCDC 1911279'
loop_
_audit_author_name
_audit_author_address
'guangyin qian'
;wuhan university
China
;
_audit_update_record             
;
2019-04-20 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 Br N O'
_chemical_formula_weight         330.22

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'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.7222(13)
_cell_length_b                   10.0218(6)
_cell_length_c                   14.5030(8)
_cell_angle_alpha                90
_cell_angle_beta                 125.646(2)
_cell_angle_gamma                90
_cell_volume                     2801.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      3.75
_cell_measurement_theta_max      68.88

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.945
_shelx_estimated_absorpt_T_min   0.649
_shelx_estimated_absorpt_T_max   0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4515
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      230(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17347
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.587
_diffrn_reflns_theta_max         68.871
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2573
_reflns_number_gt                2545
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_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)+(0.0506P)²+5.6121P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2573
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.001
_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 0.56132(2) 0.46895(3) 0.40895(2) 0.04540(15) Uani 1 1 d . . . . .
O1 O 0.90137(13) 0.3408(3) 1.01207(18) 0.0645(7) Uani 1 1 d . . . . .
N1 N 0.82415(12) 0.3598(3) 0.6322(2) 0.0390(5) Uani 1 1 d . . . . .
C1 C 0.71244(16) 0.2630(3) 0.8237(2) 0.0418(6) Uani 1 1 d . . . . .
H1 H 0.7546(18) 0.234(3) 0.885(3) 0.042(9) Uiso 1 1 d . . . . .
C2 C 0.65388(18) 0.2627(3) 0.8210(3) 0.0476(7) Uani 1 1 d . . . . .
H2 H 0.659(2) 0.237(4) 0.888(3) 0.062(11) Uiso 1 1 d . . . . .
C3 C 0.58974(17) 0.3007(3) 0.7234(3) 0.0475(7) Uani 1 1 d . . . . .
H3 H 0.549(2) 0.299(4) 0.724(4) 0.075(12) Uiso 1 1 d . . . . .
C4 C 0.58567(15) 0.3440(3) 0.6311(3) 0.0397(6) Uani 1 1 d . . . . .
H4 H 0.5427(19) 0.378(3) 0.570(3) 0.045(9) Uiso 1 1 d . . . . .
C5 C 0.64565(13) 0.3517(3) 0.6317(2) 0.0311(5) Uani 1 1 d . . . . .
C6 C 0.64538(12) 0.4026(3) 0.5407(2) 0.0304(5) Uani 1 1 d . . . . .
C8 C 0.76725(13) 0.3573(3) 0.6354(2) 0.0309(5) Uani 1 1 d . . . . .
C7 C 0.70293(13) 0.4089(3) 0.5416(2) 0.0313(5) Uani 1 1 d . . . . .
H7 H 0.6987(19) 0.446(4) 0.482(3) 0.050(10) Uiso 1 1 d . . . . .
C9 C 0.77064(13) 0.3045(3) 0.7278(2) 0.0321(5) Uani 1 1 d . . . . .
C10 C 0.71065(14) 0.3061(3) 0.7280(2) 0.0328(5) Uani 1 1 d . . . . .
C11 C 0.83808(14) 0.2451(3) 0.8261(2) 0.0389(6) Uani 1 1 d . . . . .
H11 H 0.8289(17) 0.169(3) 0.864(3) 0.046(9) Uiso 1 1 d . . . . .
C12 C 0.87824(16) 0.1913(3) 0.7807(3) 0.0432(7) Uani 1 1 d . . . . .
H12B H 0.8536(18) 0.121(4) 0.728(3) 0.049(9) Uiso 1 1 d . . . . .
H12A H 0.9243(18) 0.156(3) 0.845(3) 0.041(8) Uiso 1 1 d . . . . .
C13 C 0.89067(14) 0.3040(3) 0.7258(3) 0.0431(7) Uani 1 1 d . . . . .
H13 H 0.9168(16) 0.274(3) 0.694(3) 0.042(8) Uiso 1 1 d . . . . .
C14 C 0.93687(16) 0.4112(4) 0.8140(3) 0.0522(8) Uani 1 1 d . . . . .
H14B H 0.985(2) 0.367(4) 0.872(3) 0.058(10) Uiso 1 1 d . . . . .
H14A H 0.945(2) 0.484(4) 0.776(4) 0.062(12) Uiso 1 1 d . . . . .
C15 C 0.90572(18) 0.4631(4) 0.8745(3) 0.0491(8) Uani 1 1 d . . . . .
H15A H 0.870(2) 0.512(3) 0.826(3) 0.034(8) Uiso 1 1 d . . . . .
H15B H 0.940(2) 0.523(4) 0.936(4) 0.061(12) Uiso 1 1 d . . . . .
C16 C 0.88365(15) 0.3507(3) 0.9151(2) 0.0454(7) Uani 1 1 d . . . . .
C17 C 0.82239(16) 0.4286(3) 0.5426(3) 0.0431(7) Uani 1 1 d . . . . .
H17C H 0.794070 0.378559 0.472536 0.065 Uiso 1 1 calc R U . . .
H17B H 0.869155 0.436544 0.563158 0.065 Uiso 1 1 calc R U . . .
H17A H 0.802755 0.516931 0.532320 0.065 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 C6 1.905(2) . ?
O1 C16 1.214(4) . ?
N1 C8 1.378(3) . ?
N1 C17 1.449(4) . ?
N1 C13 1.466(4) . ?
C1 C2 1.367(4) . ?
C1 C10 1.431(4) . ?
C1 H1 0.92(4) . ?
C2 C3 1.398(5) . ?
C2 H2 0.95(4) . ?
C3 C4 1.356(4) . ?
C3 H3 0.97(4) . ?
C4 C5 1.420(4) . ?
C4 H4 0.94(4) . ?
C5 C6 1.411(4) . ?
C5 C10 1.424(4) . ?
C6 C7 1.359(4) . ?
C8 C9 1.399(4) . ?
C8 C7 1.424(4) . ?
C7 H7 0.90(4) . ?
C9 C10 1.424(4) . ?
C9 C11 1.512(4) . ?
C11 C16 1.526(4) . ?
C11 C12 1.536(4) . ?
C11 H11 1.04(3) . ?
C12 C13 1.507(5) . ?
C12 H12B 0.95(4) . ?
C12 H12A 1.00(3) . ?
C13 C14 1.535(4) . ?
C13 H13 1.01(3) . ?
C14 C15 1.531(5) . ?
C14 H14B 1.05(4) . ?
C14 H14A 0.99(4) . ?
C15 C16 1.500(5) . ?
C15 H15A 0.88(4) . ?
C15 H15B 0.99(4) . ?
C17 H17C 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17A 0.9700 . ?

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
C8 N1 C17 121.4(2) . . ?
C8 N1 C13 120.6(2) . . ?
C17 N1 C13 117.7(2) . . ?
C2 C1 C10 121.2(3) . . ?
C2 C1 H1 123(2) . . ?
C10 C1 H1 116(2) . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2 118(2) . . ?
C3 C2 H2 121(2) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 121(3) . . ?
C2 C3 H3 119(3) . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 117(2) . . ?
C5 C4 H4 121(2) . . ?
C6 C5 C4 123.7(2) . . ?
C6 C5 C10 116.4(2) . . ?
C4 C5 C10 119.8(2) . . ?
C7 C6 C5 123.4(2) . . ?
C7 C6 BR1 116.83(19) . . ?
C5 C6 BR1 119.72(18) . . ?
N1 C8 C9 121.9(2) . . ?
N1 C8 C7 119.1(2) . . ?
C9 C8 C7 119.0(2) . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 118(2) . . ?
C8 C7 H7 122(2) . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 C11 119.3(2) . . ?
C10 C9 C11 120.8(2) . . ?
C5 C10 C9 120.9(2) . . ?
C5 C10 C1 116.8(2) . . ?
C9 C10 C1 122.2(2) . . ?
C9 C11 C16 111.3(2) . . ?
C9 C11 C12 108.3(2) . . ?
C16 C11 C12 107.2(2) . . ?
C9 C11 H11 110.9(19) . . ?
C16 C11 H11 108.9(19) . . ?
C12 C11 H11 110.2(18) . . ?
C13 C12 C11 108.9(2) . . ?
C13 C12 H12B 110(2) . . ?
C11 C12 H12B 111(2) . . ?
C13 C12 H12A 108.2(19) . . ?
C11 C12 H12A 109.6(18) . . ?
H12B C12 H12A 108(3) . . ?
N1 C13 C12 109.8(2) . . ?
N1 C13 C14 111.4(3) . . ?
C12 C13 C14 110.4(3) . . ?
N1 C13 H13 107.9(18) . . ?
C12 C13 H13 112.3(19) . . ?
C14 C13 H13 104.9(19) . . ?
C15 C14 C13 111.5(3) . . ?
C15 C14 H14B 111(2) . . ?
C13 C14 H14B 107(2) . . ?
C15 C14 H14A 112(3) . . ?
C13 C14 H14A 109(3) . . ?
H14B C14 H14A 107(3) . . ?
C16 C15 C14 111.5(3) . . ?
C16 C15 H15A 109(2) . . ?
C14 C15 H15A 108(2) . . ?
C16 C15 H15B 113(2) . . ?
C14 C15 H15B 108(2) . . ?
H15A C15 H15B 107(3) . . ?
O1 C16 C15 123.5(3) . . ?
O1 C16 C11 121.3(3) . . ?
C15 C16 C11 115.2(3) . . ?
N1 C17 H17C 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
N1 C17 H17A 109.5 . . ?
H17C C17 H17A 109.5 . . ?
H17B C17 H17A 109.5 . . ?

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
C10 C1 C2 C3 2.0(5) . . . . ?
C1 C2 C3 C4 -2.8(5) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 C6 -176.4(3) . . . . ?
C3 C4 C5 C10 3.7(4) . . . . ?
C4 C5 C6 C7 -179.6(3) . . . . ?
C10 C5 C6 C7 0.3(4) . . . . ?
C4 C5 C6 BR1 1.2(4) . . . . ?
C10 C5 C6 BR1 -178.94(18) . . . . ?
C17 N1 C8 C9 -172.6(3) . . . . ?
C13 N1 C8 C9 1.2(4) . . . . ?
C17 N1 C8 C7 8.0(4) . . . . ?
C13 N1 C8 C7 -178.2(2) . . . . ?
C5 C6 C7 C8 2.8(4) . . . . ?
BR1 C6 C7 C8 -177.94(19) . . . . ?
N1 C8 C7 C6 177.3(2) . . . . ?
C9 C8 C7 C6 -2.1(4) . . . . ?
N1 C8 C9 C10 179.0(2) . . . . ?
C7 C8 C9 C10 -1.5(4) . . . . ?
N1 C8 C9 C11 -1.5(4) . . . . ?
C7 C8 C9 C11 177.9(2) . . . . ?
C6 C5 C10 C9 -4.0(4) . . . . ?
C4 C5 C10 C9 175.8(2) . . . . ?
C6 C5 C10 C1 175.8(2) . . . . ?
C4 C5 C10 C1 -4.4(4) . . . . ?
C8 C9 C10 C5 4.7(4) . . . . ?
C11 C9 C10 C5 -174.7(2) . . . . ?
C8 C9 C10 C1 -175.1(3) . . . . ?
C11 C9 C10 C1 5.5(4) . . . . ?
C2 C1 C10 C5 1.6(4) . . . . ?
C2 C1 C10 C9 -178.6(3) . . . . ?
C8 C9 C11 C16 89.1(3) . . . . ?
C10 C9 C11 C16 -91.5(3) . . . . ?
C8 C9 C11 C12 -28.5(4) . . . . ?
C10 C9 C11 C12 150.9(3) . . . . ?
C9 C11 C12 C13 58.5(3) . . . . ?
C16 C11 C12 C13 -61.7(3) . . . . ?
C8 N1 C13 C12 30.1(4) . . . . ?
C17 N1 C13 C12 -155.9(3) . . . . ?
C8 N1 C13 C14 -92.6(3) . . . . ?
C17 N1 C13 C14 81.4(3) . . . . ?
C11 C12 C13 N1 -59.8(3) . . . . ?
C11 C12 C13 C14 63.5(3) . . . . ?
N1 C13 C14 C15 66.1(4) . . . . ?
C12 C13 C14 C15 -56.2(4) . . . . ?
C13 C14 C15 C16 48.3(4) . . . . ?
C14 C15 C16 O1 128.0(3) . . . . ?
C14 C15 C16 C11 -50.5(4) . . . . ?
C9 C11 C16 O1 119.9(3) . . . . ?
C12 C11 C16 O1 -121.8(3) . . . . ?
C9 C11 C16 C15 -61.6(3) . . . . ?
C12 C11 C16 C15 56.6(3) . . . . ?

_refine_diff_density_max         0.718
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.082

