# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2017036'
loop_
_audit_author_name
_audit_author_address
'Xueliang Huang'
;Fujian Institute of Research on the Structure of Matter,  Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2020-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Br N2 O2'
_chemical_formula_weight         385.26

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           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.495(2)
_cell_length_b                   21.897(4)
_cell_length_c                   7.8420(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.57(3)
_cell_angle_gamma                90.00
_cell_volume                     1790.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4946
_cell_measurement_theta_min      3.0741
_cell_measurement_theta_max      27.5865

_exptl_crystal_description       Prism
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    2.309
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6318
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14826
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4093
_reflns_number_gt                2584
_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)+(0.0875P)²+0.0756P] 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         4093
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_ref         0.2131
_refine_ls_wR_factor_gt          0.1888
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.199
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.006

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 0.86752(6) 0.12049(3) 0.04645(8) 0.1040(3) Uani 1 1 d . . .
O1 O 0.4857(4) 0.06245(14) 0.3495(5) 0.1031(12) Uani 1 1 d . . .
O2 O 0.2823(3) 0.08338(13) 0.3901(5) 0.0887(10) Uani 1 1 d . . .
N1 N 0.5162(3) 0.19015(14) 0.2728(4) 0.0608(8) Uani 1 1 d . . .
N2 N 0.5095(3) 0.25144(14) 0.2710(4) 0.0617(8) Uani 1 1 d . . .
C1 C 0.4470(5) 0.37619(17) 0.3149(6) 0.0714(11) Uani 1 1 d . . .
H1 H 0.5239 0.3661 0.2737 0.086 Uiso 1 1 calc R . .
C2 C 0.4174(6) 0.4359(2) 0.3357(7) 0.0952(16) Uani 1 1 d . . .
H2 H 0.4744 0.4662 0.3099 0.114 Uiso 1 1 calc R . .
C3 C 0.3019(6) 0.4521(2) 0.3957(7) 0.0956(16) Uani 1 1 d . . .
H3 H 0.2812 0.4930 0.4087 0.115 Uiso 1 1 calc R . .
C4 C 0.2202(5) 0.4076(2) 0.4349(7) 0.0888(14) Uani 1 1 d . . .
H4 H 0.1430 0.4181 0.4748 0.107 Uiso 1 1 calc R . .
C5 C 0.2512(4) 0.34618(18) 0.4158(5) 0.0677(10) Uani 1 1 d . . .
H5 H 0.1953 0.3159 0.4449 0.081 Uiso 1 1 calc R . .
C6 C 0.3648(4) 0.33015(17) 0.3538(4) 0.0552(8) Uani 1 1 d . . .
C7 C 0.3997(3) 0.26559(16) 0.3348(4) 0.0527(8) Uani 1 1 d . . .
C8 C 0.3352(3) 0.21242(16) 0.3751(5) 0.0553(8) Uani 1 1 d . . .
H8 H 0.2565 0.2099 0.4184 0.066 Uiso 1 1 calc R . .
C9 C 0.4131(4) 0.16446(16) 0.3366(5) 0.0576(9) Uani 1 1 d . . .
C10 C 0.4007(5) 0.0982(2) 0.3566(6) 0.0738(12) Uani 1 1 d . . .
C13 C 0.6258(4) 0.1625(2) 0.2051(6) 0.0709(11) Uani 1 1 d . . .
H13A H 0.6401 0.1830 0.0993 0.085 Uiso 1 1 calc R . .
H13B H 0.6068 0.1200 0.1784 0.085 Uiso 1 1 calc R . .
C12 C 0.1350(6) -0.0001(4) 0.3749(18) 0.238(6) Uani 1 1 d D . .
H12A H 0.0868 0.0348 0.3305 0.357 Uiso 1 1 calc R . .
H12B H 0.1018 -0.0143 0.4768 0.357 Uiso 1 1 calc R . .
H12C H 0.1282 -0.0320 0.2903 0.357 Uiso 1 1 calc R . .
C11 C 0.2730(6) 0.0174(2) 0.4171(12) 0.151(3) Uani 1 1 d D . .
H11A H 0.3023 0.0072 0.5355 0.181 Uiso 1 1 calc R . .
H11B H 0.3258 -0.0043 0.3433 0.181 Uiso 1 1 calc R . .
C14 C 0.7464(4) 0.16609(17) 0.3288(5) 0.0588(9) Uani 1 1 d . . .
C15 C 0.8642(4) 0.14994(18) 0.2744(6) 0.0687(10) Uani 1 1 d . . .
C16 C 0.9771(5) 0.1541(2) 0.3770(8) 0.0907(14) Uani 1 1 d . . .
H16 H 1.0534 0.1425 0.3362 0.109 Uiso 1 1 calc R . .
C17 C 0.9777(5) 0.1755(2) 0.5419(9) 0.0987(17) Uani 1 1 d . . .
H17 H 1.0547 0.1791 0.6127 0.118 Uiso 1 1 calc R . .
C18 C 0.8632(6) 0.1919(2) 0.6025(7) 0.0904(15) Uani 1 1 d . . .
H18 H 0.8633 0.2060 0.7144 0.109 Uiso 1 1 calc R . .
C19 C 0.7491(4) 0.18707(18) 0.4961(6) 0.0705(11) Uani 1 1 d . . .
H19 H 0.6728 0.1981 0.5375 0.085 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 C15 1.904(5) . ?
O1 C10 1.193(5) . ?
O2 C10 1.340(6) . ?
O2 C11 1.465(6) . ?
N1 N2 1.344(4) . ?
N1 C9 1.364(5) . ?
N1 C13 1.454(5) . ?
N2 C7 1.344(5) . ?
C1 C2 1.359(6) . ?
C1 C6 1.383(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.472(5) . ?
C7 C8 1.401(5) . ?
C8 C9 1.386(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.466(6) . ?
C13 C14 1.506(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11 1.4977(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C14 C19 1.388(6) . ?
C14 C15 1.399(5) . ?
C15 C16 1.357(7) . ?
C16 C17 1.375(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(7) . ?
C18 H18 0.9300 . ?
C19 H19 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
C10 O2 C11 110.2(4) . . ?
N2 N1 C9 111.9(3) . . ?
N2 N1 C13 117.0(3) . . ?
C9 N1 C13 131.0(3) . . ?
N1 N2 C7 105.8(3) . . ?
C2 C1 C6 121.2(5) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 120.3(5) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.4(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C1 C6 C5 118.5(4) . . ?
C1 C6 C7 120.6(4) . . ?
C5 C6 C7 120.9(3) . . ?
N2 C7 C8 110.5(3) . . ?
N2 C7 C6 119.5(3) . . ?
C8 C7 C6 130.0(3) . . ?
C9 C8 C7 105.5(3) . . ?
C9 C8 H8 127.2 . . ?
C7 C8 H8 127.2 . . ?
N1 C9 C8 106.3(3) . . ?
N1 C9 C10 122.1(4) . . ?
C8 C9 C10 131.7(4) . . ?
O1 C10 O2 124.4(4) . . ?
O1 C10 C9 124.7(4) . . ?
O2 C10 C9 110.9(4) . . ?
N1 C13 C14 112.7(3) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C11 C12 107.4(5) . . ?
O2 C11 H11A 110.2 . . ?
C12 C11 H11A 110.3 . . ?
O2 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C19 C14 C15 116.7(4) . . ?
C19 C14 C13 123.5(3) . . ?
C15 C14 C13 119.8(4) . . ?
C16 C15 C14 123.0(5) . . ?
C16 C15 Br1 118.1(4) . . ?
C14 C15 Br1 118.9(3) . . ?
C15 C16 C17 119.3(5) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.0(5) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.8(5) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 121.2(4) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?

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
C9 N1 N2 C7 -0.1(4) . . . . ?
C13 N1 N2 C7 178.4(3) . . . . ?
C6 C1 C2 C3 -0.7(8) . . . . ?
C1 C2 C3 C4 0.8(9) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C3 C4 C5 C6 -1.1(7) . . . . ?
C2 C1 C6 C5 -0.3(7) . . . . ?
C2 C1 C6 C7 -178.4(4) . . . . ?
C4 C5 C6 C1 1.2(6) . . . . ?
C4 C5 C6 C7 179.3(4) . . . . ?
N1 N2 C7 C8 -0.9(4) . . . . ?
N1 N2 C7 C6 178.7(3) . . . . ?
C1 C6 C7 N2 -3.3(5) . . . . ?
C5 C6 C7 N2 178.7(3) . . . . ?
C1 C6 C7 C8 176.2(4) . . . . ?
C5 C6 C7 C8 -1.8(6) . . . . ?
N2 C7 C8 C9 1.5(4) . . . . ?
C6 C7 C8 C9 -178.0(3) . . . . ?
N2 N1 C9 C8 1.0(4) . . . . ?
C13 N1 C9 C8 -177.2(4) . . . . ?
N2 N1 C9 C10 -178.0(3) . . . . ?
C13 N1 C9 C10 3.8(6) . . . . ?
C7 C8 C9 N1 -1.5(4) . . . . ?
C7 C8 C9 C10 177.4(4) . . . . ?
C11 O2 C10 O1 0.2(7) . . . . ?
C11 O2 C10 C9 -177.6(4) . . . . ?
N1 C9 C10 O1 13.9(7) . . . . ?
C8 C9 C10 O1 -164.8(4) . . . . ?
N1 C9 C10 O2 -168.3(4) . . . . ?
C8 C9 C10 O2 13.0(6) . . . . ?
N2 N1 C13 C14 77.2(5) . . . . ?
C9 N1 C13 C14 -104.6(5) . . . . ?
C10 O2 C11 C12 -154.9(8) . . . . ?
N1 C13 C14 C19 7.0(6) . . . . ?
N1 C13 C14 C15 -170.5(4) . . . . ?
C19 C14 C15 C16 0.0(6) . . . . ?
C13 C14 C15 C16 177.6(4) . . . . ?
C19 C14 C15 Br1 179.8(3) . . . . ?
C13 C14 C15 Br1 -2.6(5) . . . . ?
C14 C15 C16 C17 -0.6(7) . . . . ?
Br1 C15 C16 C17 179.6(4) . . . . ?
C15 C16 C17 C18 0.9(8) . . . . ?
C16 C17 C18 C19 -0.6(8) . . . . ?
C17 C18 C19 C14 0.0(8) . . . . ?
C15 C14 C19 C18 0.3(6) . . . . ?
C13 C14 C19 C18 -177.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.073
