# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_201916-1
_database_code_depnum_ccdc_archive 'CCDC 2049643'
loop_
_audit_author_name
_audit_author_address
'Yu-Chao Wang'
;Jiangxi University of Science and Technology
China
;
_audit_update_record             
;
2020-12-11 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Br N O2'
_chemical_formula_weight         358.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9145(7)
_cell_length_b                   9.9325(8)
_cell_length_c                   10.1186(8)
_cell_angle_alpha                87.116(6)
_cell_angle_beta                 69.183(7)
_cell_angle_gamma                70.272(7)
_cell_volume                     785.82(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1705
_cell_measurement_theta_min      3.8960
_cell_measurement_theta_max      27.4690

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    2.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5265
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_sigmaI/netI    0.0868
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2737
_reflns_number_gt                1905
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.9012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2737
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.52251(8) 0.21058(7) 0.31232(8) 0.0619(3) Uani 1 1 d . . .
O1 O 0.6363(5) 0.2672(4) 0.8740(5) 0.0533(11) Uani 1 1 d . . .
O2 O 0.7963(5) -0.0047(5) 0.4406(5) 0.0677(14) Uani 1 1 d . . .
N1 N 0.6309(5) 0.1032(5) 0.6680(6) 0.0467(13) Uani 1 1 d . . .
C6 C 0.4183(6) 0.2805(5) 0.6110(6) 0.0378(13) Uani 1 1 d . . .
C13 C 0.2585(6) 0.4019(5) 0.6288(6) 0.0359(13) Uani 1 1 d . . .
C8 C 0.5297(7) 0.3367(6) 0.7952(7) 0.0456(15) Uani 1 1 d . . .
H8 H 0.5916 0.3827 0.7171 0.055 Uiso 1 1 calc R . .
C7 C 0.4777(6) 0.2269(6) 0.7344(7) 0.0441(15) Uani 1 1 d . . .
C5 C 0.5268(7) 0.1953(6) 0.4964(6) 0.0428(14) Uani 1 1 d . . .
C18 C 0.1089(7) 0.3769(6) 0.6507(6) 0.0438(14) Uani 1 1 d . . .
H18 H 0.1083 0.2834 0.6523 0.053 Uiso 1 1 calc R . .
C4 C 0.6702(7) 0.0848(6) 0.5256(8) 0.0502(17) Uani 1 1 d . . .
C9 C 0.3798(8) 0.4487(6) 0.8970(8) 0.0569(18) Uani 1 1 d . . .
H9 H 0.3842 0.5394 0.9087 0.068 Uiso 1 1 calc R . .
C14 C 0.2587(7) 0.5410(6) 0.6216(7) 0.0489(16) Uani 1 1 d . . .
H14 H 0.3597 0.5587 0.6046 0.059 Uiso 1 1 calc R . .
C12 C 0.3400(7) 0.1871(6) 0.8478(7) 0.0486(15) Uani 1 1 d . . .
H12 H 0.3345 0.0958 0.8425 0.058 Uiso 1 1 calc R . .
C15 C 0.1097(8) 0.6536(6) 0.6395(7) 0.0556(17) Uani 1 1 d . . .
H15 H 0.1105 0.7471 0.6350 0.067 Uiso 1 1 calc R . .
C16 C -0.0396(7) 0.6290(7) 0.6637(7) 0.0536(17) Uani 1 1 d . . .
H16 H -0.1400 0.7053 0.6757 0.064 Uiso 1 1 calc R . .
C17 C -0.0399(7) 0.4908(7) 0.6703(7) 0.0534(17) Uani 1 1 d . . .
H17 H -0.1415 0.4737 0.6881 0.064 Uiso 1 1 calc R . .
C3 C 0.7488(8) 0.0409(6) 0.7387(8) 0.0596(19) Uani 1 1 d . . .
H3A H 0.8520 -0.0283 0.6736 0.072 Uiso 1 1 calc R . .
H3B H 0.6986 -0.0089 0.8178 0.072 Uiso 1 1 calc R . .
C10 C 0.2401(9) 0.4193(7) 0.9710(7) 0.0635(19) Uani 1 1 d . . .
H10 H 0.1481 0.4898 1.0353 0.076 Uiso 1 1 calc R . .
C2 C 0.7921(7) 0.1568(7) 0.7918(8) 0.0562(17) Uani 1 1 d . . .
H2 H 0.8560 0.1981 0.7104 0.067 Uiso 1 1 calc R . .
C11 C 0.2272(8) 0.2802(7) 0.9543(7) 0.0605(18) Uani 1 1 d . . .
H11 H 0.1379 0.2563 1.0198 0.073 Uiso 1 1 calc R . .
C1 C 0.8942(9) 0.1053(8) 0.8858(9) 0.077(2) Uani 1 1 d . . .
H1A H 0.9153 0.1843 0.9175 0.116 Uiso 1 1 calc R . .
H1B H 1.0011 0.0327 0.8338 0.116 Uiso 1 1 calc R . .
H1C H 0.8317 0.0658 0.9664 0.116 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 C5 1.874(6) . ?
O1 C8 1.434(7) . ?
O1 C2 1.438(7) . ?
O2 C4 1.228(7) . ?
N1 C4 1.363(8) . ?
N1 C3 1.432(8) . ?
N1 C7 1.457(6) . ?
C6 C5 1.322(7) . ?
C6 C13 1.482(7) . ?
C6 C7 1.528(8) . ?
C13 C18 1.377(7) . ?
C13 C14 1.381(8) . ?
C8 C9 1.489(8) . ?
C8 C7 1.547(7) . ?
C8 H8 0.9800 . ?
C7 C12 1.503(8) . ?
C5 C4 1.487(8) . ?
C18 C17 1.379(8) . ?
C18 H18 0.9300 . ?
C9 C10 1.326(10) . ?
C9 H9 0.9300 . ?
C14 C15 1.376(8) . ?
C14 H14 0.9300 . ?
C12 C11 1.315(8) . ?
C12 H12 0.9300 . ?
C15 C16 1.368(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(9) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C3 C2 1.507(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C10 C11 1.448(10) . ?
C10 H10 0.9300 . ?
C2 C1 1.500(9) . ?
C2 H2 0.9800 . ?
C11 H11 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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 O1 C2 113.9(5) . . ?
C4 N1 C3 124.3(5) . . ?
C4 N1 C7 112.3(5) . . ?
C3 N1 C7 120.7(5) . . ?
C5 C6 C13 129.1(6) . . ?
C5 C6 C7 107.9(5) . . ?
C13 C6 C7 122.8(5) . . ?
C18 C13 C14 119.4(5) . . ?
C18 C13 C6 120.4(5) . . ?
C14 C13 C6 120.3(5) . . ?
O1 C8 C9 105.5(5) . . ?
O1 C8 C7 110.6(4) . . ?
C9 C8 C7 112.4(5) . . ?
O1 C8 H8 109.4 . . ?
C9 C8 H8 109.4 . . ?
C7 C8 H8 109.4 . . ?
N1 C7 C12 112.6(5) . . ?
N1 C7 C6 102.8(5) . . ?
C12 C7 C6 109.3(4) . . ?
N1 C7 C8 108.0(4) . . ?
C12 C7 C8 111.1(5) . . ?
C6 C7 C8 112.8(5) . . ?
C6 C5 C4 111.6(6) . . ?
C6 C5 Br1 127.3(5) . . ?
C4 C5 Br1 120.9(4) . . ?
C13 C18 C17 119.9(5) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
O2 C4 N1 127.1(6) . . ?
O2 C4 C5 127.8(7) . . ?
N1 C4 C5 105.1(5) . . ?
C10 C9 C8 120.1(6) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C15 C14 C13 120.1(5) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C11 C12 C7 120.7(6) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C16 C15 C14 120.5(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.5(5) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.6(6) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
N1 C3 C2 109.8(5) . . ?
N1 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C9 C10 C11 121.6(6) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
O1 C2 C1 106.9(5) . . ?
O1 C2 C3 108.9(5) . . ?
C1 C2 C3 113.6(6) . . ?
O1 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C12 C11 C10 120.8(6) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.825
_refine_diff_density_min         -1.076
_refine_diff_density_rms         0.105
