# Electronic Supplementary Material (ESI) for ChemComm.
# 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_exp_10294
_database_code_depnum_ccdc_archive 'CCDC 2014883'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2021-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 Br N2 O2'
_chemical_formula_weight         395.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.3888(11)
_cell_length_b                   9.2869(12)
_cell_length_c                   23.322(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1816.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    659
_cell_measurement_theta_min      5.6140
_cell_measurement_theta_max      45.7990

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    3.206
_shelx_estimated_absorpt_T_min   0.681
_shelx_estimated_absorpt_T_max   0.719
_exptl_absorpt_correction_T_min  0.23611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4537
_diffrn_reflns_av_unetI/netI     0.1562
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.791
_diffrn_reflns_theta_max         67.233
_diffrn_reflns_theta_full        67.233
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_point_group_measured_fraction_full 0.884
_reflns_number_total             2857
_reflns_number_gt                1254
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.525
_reflns_Friedel_fraction_max     0.725
_reflns_Friedel_fraction_full    0.725

_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       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0463P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 193 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(6)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2857
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1658
_refine_ls_R_factor_gt           0.0831
_refine_ls_wR_factor_ref         0.2058
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.7395(3) 0.2031(2) 0.55741(9) 0.0862(7) Uani 1 1 d . . . . .
N1 N 0.899(2) 0.4926(17) 0.3035(7) 0.100(6) Uani 1 1 d . . . . .
N2 N 1.258(2) 0.6472(16) 0.4158(7) 0.090(5) Uani 1 1 d . . . . .
O1 O 1.1510(14) 0.7938(13) 0.2893(5) 0.072(3) Uani 1 1 d . . . . .
H1 H 1.169386 0.856490 0.265460 0.108 Uiso 1 1 calc R U . . .
O2 O 0.7100(12) 0.7692(11) 0.3769(5) 0.064(3) Uani 1 1 d . . . . .
C1 C 0.768(3) 0.3725(15) 0.5140(7) 0.064(5) Uani 1 1 d . . . . .
C2 C 0.887(2) 0.4701(18) 0.5295(8) 0.071(5) Uani 1 1 d . . . . .
H2 H 0.949382 0.453228 0.561658 0.085 Uiso 1 1 calc R U . . .
C3 C 0.910(2) 0.5917(17) 0.4970(7) 0.061(5) Uani 1 1 d . . . . .
H3 H 0.986344 0.658324 0.508310 0.074 Uiso 1 1 calc R U . . .
C4 C 0.8227(19) 0.6176(17) 0.4480(7) 0.059(4) Uani 1 1 d . . . . .
C5 C 0.7014(18) 0.5208(17) 0.4337(8) 0.070(5) Uani 1 1 d . . . . .
H5 H 0.635750 0.539415 0.402415 0.084 Uiso 1 1 calc R U . . .
C6 C 0.679(2) 0.3977(18) 0.4659(8) 0.075(6) Uani 1 1 d . . . . .
H6 H 0.601705 0.331133 0.454856 0.089 Uiso 1 1 calc R U . . .
C7 C 0.8537(19) 0.7460(17) 0.4102(7) 0.056(4) Uani 1 1 d . . . . .
C8 C 0.9866(18) 0.711(2) 0.3648(7) 0.056(4) Uani 1 1 d . . . . .
C9 C 1.020(2) 0.8354(17) 0.3233(8) 0.062(5) Uani 1 1 d . . . . .
H9 H 0.926445 0.849450 0.298526 0.074 Uiso 1 1 calc R U . . .
C10 C 1.053(2) 0.9748(18) 0.3562(7) 0.066(5) Uani 1 1 d . . . . .
H10A H 1.061870 1.054318 0.329444 0.079 Uiso 1 1 calc R U . . .
H10B H 1.153184 0.966222 0.376614 0.079 Uiso 1 1 calc R U . . .
C11 C 0.915(2) 1.0063(16) 0.4000(7) 0.063(5) Uani 1 1 d . . . . .
H11 H 0.940243 1.095362 0.420706 0.076 Uiso 1 1 calc R U . . .
C12 C 0.8973(18) 0.8865(17) 0.4423(7) 0.066(5) Uani 1 1 d . . . . .
H12A H 0.814184 0.910160 0.469667 0.079 Uiso 1 1 calc R U . . .
H12B H 0.996222 0.873351 0.463247 0.079 Uiso 1 1 calc R U . . .
C13 C 0.759(2) 1.0266(18) 0.3675(7) 0.065(4) Uani 1 1 d . . . . .
C14 C 0.708(2) 1.1617(19) 0.3462(7) 0.075(6) Uani 1 1 d . . . . .
H14 H 0.766384 1.245164 0.352504 0.090 Uiso 1 1 calc R U . . .
C15 C 0.567(2) 1.164(2) 0.3159(9) 0.088(7) Uani 1 1 d . . . . .
H15 H 0.531071 1.250930 0.301257 0.105 Uiso 1 1 calc R U . . .
C16 C 0.480(2) 1.043(2) 0.3066(9) 0.092(7) Uani 1 1 d . . . . .
H16 H 0.386624 1.051370 0.285358 0.111 Uiso 1 1 calc R U . . .
C17 C 0.523(2) 0.911(2) 0.3268(8) 0.077(6) Uani 1 1 d . . . . .
H17 H 0.461628 0.829298 0.320108 0.093 Uiso 1 1 calc R U . . .
C18 C 0.666(2) 0.907(2) 0.3586(8) 0.070(5) Uani 1 1 d . . . . .
C19 C 0.942(2) 0.587(2) 0.3301(8) 0.072(6) Uani 1 1 d . . . . .
C20 C 1.141(2) 0.6681(17) 0.3944(8) 0.062(5) 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 C1 1.886(14) . ?
N1 C19 1.13(2) . ?
N2 C20 1.12(2) . ?
O1 C9 1.411(17) . ?
O2 C18 1.395(19) . ?
O2 C7 1.451(17) . ?
C1 C6 1.37(2) . ?
C1 C2 1.39(2) . ?
C2 C3 1.375(19) . ?
C3 C4 1.38(2) . ?
C4 C5 1.40(2) . ?
C4 C7 1.51(2) . ?
C5 C6 1.38(2) . ?
C7 C12 1.549(19) . ?
C7 C8 1.57(2) . ?
C8 C19 1.45(2) . ?
C8 C20 1.52(2) . ?
C8 C9 1.54(2) . ?
C9 C10 1.53(2) . ?
C10 C11 1.57(2) . ?
C11 C12 1.50(2) . ?
C11 C13 1.53(2) . ?
C13 C18 1.37(2) . ?
C13 C14 1.42(2) . ?
C14 C15 1.37(2) . ?
C15 C16 1.35(3) . ?
C16 C17 1.36(2) . ?
C17 C18 1.41(2) . ?

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
C18 O2 C7 121.2(13) . . ?
C6 C1 C2 119.5(15) . . ?
C6 C1 Br1 120.7(14) . . ?
C2 C1 Br1 119.7(14) . . ?
C3 C2 C1 119.5(18) . . ?
C2 C3 C4 121.7(17) . . ?
C3 C4 C5 118.2(16) . . ?
C3 C4 C7 122.1(16) . . ?
C5 C4 C7 119.7(17) . . ?
C6 C5 C4 120.2(17) . . ?
C1 C6 C5 120.7(17) . . ?
O2 C7 C4 106.7(13) . . ?
O2 C7 C12 109.3(13) . . ?
C4 C7 C12 115.1(14) . . ?
O2 C7 C8 105.1(12) . . ?
C4 C7 C8 110.5(14) . . ?
C12 C7 C8 109.6(14) . . ?
C19 C8 C20 105.7(16) . . ?
C19 C8 C9 106.8(14) . . ?
C20 C8 C9 109.2(14) . . ?
C19 C8 C7 110.9(14) . . ?
C20 C8 C7 110.7(14) . . ?
C9 C8 C7 113.2(15) . . ?
O1 C9 C10 111.8(14) . . ?
O1 C9 C8 106.7(13) . . ?
C10 C9 C8 110.8(15) . . ?
C9 C10 C11 110.5(14) . . ?
C12 C11 C13 109.3(14) . . ?
C12 C11 C10 111.5(14) . . ?
C13 C11 C10 109.5(14) . . ?
C11 C12 C7 109.3(13) . . ?
C18 C13 C14 119.7(19) . . ?
C18 C13 C11 117.5(16) . . ?
C14 C13 C11 122.8(17) . . ?
C15 C14 C13 116.9(19) . . ?
C16 C15 C14 122(2) . . ?
C15 C16 C17 123(2) . . ?
C16 C17 C18 116(2) . . ?
C13 C18 O2 123.2(16) . . ?
C13 C18 C17 122(2) . . ?
O2 C18 C17 114.3(17) . . ?
N1 C19 C8 177(2) . . ?
N2 C20 C8 175(2) . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.084

