# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_zhaojb190523_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1970687'
loop_
_audit_author_name
_audit_author_address
'Kuizhan Shao'
;Department of Chemistry, Northeast Normal University
China
;
_audit_update_record             
;
2020-08-09 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;
_audit_creation_date             2019-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H26 Br N O'
_chemical_formula_sum            'C27 H26 Br N O'
_chemical_formula_weight         460.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Br Br -0.6763 1.2805 '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'

_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.
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.6932(5)
_cell_length_b                   10.7179(6)
_cell_length_c                   21.8420(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2269.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.163
_cell_measurement_theta_min      4.048
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.595
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             952
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21847
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.693
_diffrn_reflns_theta_min         4.048
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3921
_reflns_number_total             4191
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1571 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0264P)²+0.8511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0640
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br01 Br 0.52968(4) 0.38306(3) 0.76945(2) 0.03663(11) Uani 1 1 d . . . . .
O1 O 0.2082(2) 0.8647(2) 0.52257(11) 0.0429(6) Uani 1 1 d . . . . .
N1 N 0.3194(3) 0.6526(3) 0.58537(12) 0.0271(6) Uani 1 1 d . . . . .
C1 C -0.0227(4) 0.6408(4) 0.88582(16) 0.0468(9) Uani 1 1 d . . . . .
H1 H -0.0785 0.6066 0.9161 0.056 Uiso 1 1 calc R . . . .
C2 C 0.0063(4) 0.7670(4) 0.88606(17) 0.0451(10) Uani 1 1 d . . . . .
H2 H -0.0305 0.8182 0.9163 0.054 Uiso 1 1 calc R . . . .
C3 C 0.0901(4) 0.8165(4) 0.84125(18) 0.0414(9) Uani 1 1 d . . . . .
H3 H 0.1097 0.9015 0.8415 0.050 Uiso 1 1 calc R . . . .
C4 C 0.1450(4) 0.7418(3) 0.79623(17) 0.0349(8) Uani 1 1 d . . . . .
H4 H 0.2012 0.7768 0.7663 0.042 Uiso 1 1 calc R . . . .
C5 C 0.1174(3) 0.6133(3) 0.79490(14) 0.0283(7) Uani 1 1 d . . . . .
C6 C 0.0318(4) 0.5652(3) 0.84025(16) 0.0379(8) Uani 1 1 d . . . . .
H6 H 0.0106 0.4806 0.8400 0.045 Uiso 1 1 calc R . . . .
C7 C 0.1699(3) 0.5300(3) 0.74722(14) 0.0306(8) Uani 1 1 d . . . . .
H7 H 0.1271 0.4526 0.7439 0.037 Uiso 1 1 calc R . . . .
C8 C 0.2719(3) 0.5525(3) 0.70813(15) 0.0284(7) Uani 1 1 d . . . . .
H8 H 0.3215 0.6263 0.7126 0.034 Uiso 1 1 calc R . . . .
C9 C 0.3108(3) 0.4674(3) 0.65821(15) 0.0295(7) Uani 1 1 d . . . . .
H9 H 0.2640 0.3864 0.6583 0.035 Uiso 1 1 calc R . . . .
C10 C 0.3408(3) 0.5214(3) 0.59558(15) 0.0276(7) Uani 1 1 d . . . . .
H10 H 0.3107 0.4684 0.5616 0.033 Uiso 1 1 calc R . . . .
C11 C 0.4578(4) 0.4669(3) 0.63271(13) 0.0252(6) Uani 1 1 d . . . . .
C12 C 0.1725(3) 0.6858(4) 0.58871(16) 0.0358(8) Uani 1 1 d . . . . .
H12A H 0.1352 0.6611 0.6281 0.043 Uiso 1 1 calc R . . . .
H12B H 0.1218 0.6422 0.5570 0.043 Uiso 1 1 calc R . . . .
C13 C 0.1571(4) 0.8239(4) 0.58048(17) 0.0422(9) Uani 1 1 d . . . . .
H13A H 0.0604 0.8460 0.5839 0.051 Uiso 1 1 calc R . . . .
H13B H 0.2068 0.8666 0.6128 0.051 Uiso 1 1 calc R . . . .
C14 C 0.3500(4) 0.8296(3) 0.51595(19) 0.0405(9) Uani 1 1 d . . . . .
H14A H 0.4053 0.8740 0.5459 0.049 Uiso 1 1 calc R . . . .
H14B H 0.3822 0.8531 0.4755 0.049 Uiso 1 1 calc R . . . .
C15 C 0.3685(4) 0.6906(3) 0.52469(15) 0.0315(8) Uani 1 1 d . . . . .
H15A H 0.3174 0.6461 0.4934 0.038 Uiso 1 1 calc R . . . .
H15B H 0.4653 0.6693 0.5205 0.038 Uiso 1 1 calc R . . . .
C16 C 0.5164(4) 0.3471(3) 0.60666(13) 0.0295(7) Uani 1 1 d . . . . .
C17 C 0.4816(6) 0.2312(3) 0.62797(18) 0.0565(12) Uani 1 1 d . . . . .
H17 H 0.4163 0.2233 0.6589 0.068 Uiso 1 1 calc R . . . .
C18 C 0.5437(6) 0.1246(4) 0.6034(2) 0.0728(15) Uani 1 1 d . . . . .
H18 H 0.5201 0.0462 0.6184 0.087 Uiso 1 1 calc R . . . .
C19 C 0.6383(6) 0.1347(4) 0.55781(18) 0.0616(13) Uani 1 1 d . . . . .
H19 H 0.6781 0.0632 0.5413 0.074 Uiso 1 1 calc R . . . .
C20 C 0.6747(4) 0.2485(4) 0.53632(17) 0.0441(10) Uani 1 1 d . . . . .
H20 H 0.7400 0.2550 0.5053 0.053 Uiso 1 1 calc R . . . .
C21 C 0.6152(4) 0.3552(3) 0.56039(15) 0.0332(8) Uani 1 1 d . . . . .
H21 H 0.6413 0.4330 0.5456 0.040 Uiso 1 1 calc R . . . .
C22 C 0.5655(3) 0.5445(3) 0.66453(14) 0.0243(7) Uani 1 1 d . . . . .
C23 C 0.6123(3) 0.5149(3) 0.72341(15) 0.0276(7) Uani 1 1 d . . . . .
C24 C 0.7205(3) 0.5757(3) 0.75079(16) 0.0346(8) Uani 1 1 d . . . . .
H24 H 0.7495 0.5523 0.7897 0.042 Uiso 1 1 calc R . . . .
C25 C 0.7864(4) 0.6718(3) 0.72038(19) 0.0403(9) Uani 1 1 d . . . . .
H25 H 0.8598 0.7135 0.7386 0.048 Uiso 1 1 calc R . . . .
C26 C 0.7420(4) 0.7051(3) 0.66257(18) 0.0379(9) Uani 1 1 d . . . . .
H26 H 0.7851 0.7702 0.6419 0.046 Uiso 1 1 calc R . . . .
C27 C 0.6336(3) 0.6422(3) 0.63525(16) 0.0320(8) Uani 1 1 d . . . . .
H27 H 0.6054 0.6657 0.5962 0.038 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
Br01 C23 1.910(3) . ?
O1 C13 1.427(4) . ?
O1 C14 1.433(4) . ?
N1 C10 1.439(4) . ?
N1 C12 1.469(4) . ?
N1 C15 1.466(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.381(5) . ?
C1 C6 1.388(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.403(5) . ?
C5 C6 1.391(5) . ?
C5 C7 1.464(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.329(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.471(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.514(5) . ?
C9 C11 1.530(5) . ?
C10 H10 0.9800 . ?
C10 C11 1.512(5) . ?
C11 C16 1.515(4) . ?
C11 C22 1.504(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.498(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.512(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.369(5) . ?
C16 C21 1.395(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.399(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.357(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.354(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.400(5) . ?
C22 C27 1.393(4) . ?
C23 C24 1.372(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.381(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.384(5) . ?
C27 H27 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
C13 O1 C14 110.0(3) . . ?
C10 N1 C12 111.6(3) . . ?
C10 N1 C15 111.4(3) . . ?
C15 N1 C12 107.0(3) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.8(3) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C7 123.2(3) . . ?
C6 C5 C4 117.6(3) . . ?
C6 C5 C7 119.2(3) . . ?
C1 C6 C5 121.4(3) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C5 C7 H7 116.4 . . ?
C8 C7 C5 127.2(3) . . ?
C8 C7 H7 116.4 . . ?
C7 C8 H8 118.2 . . ?
C7 C8 C9 123.7(3) . . ?
C9 C8 H8 118.2 . . ?
C8 C9 H9 115.4 . . ?
C8 C9 C10 118.8(3) . . ?
C8 C9 C11 120.7(3) . . ?
C10 C9 H9 115.4 . . ?
C10 C9 C11 59.6(2) . . ?
C11 C9 H9 115.4 . . ?
N1 C10 C9 119.1(3) . . ?
N1 C10 H10 114.0 . . ?
N1 C10 C11 124.7(3) . . ?
C9 C10 H10 114.0 . . ?
C11 C10 C9 60.7(2) . . ?
C11 C10 H10 114.0 . . ?
C10 C11 C9 59.7(2) . . ?
C10 C11 C16 114.0(3) . . ?
C16 C11 C9 119.2(3) . . ?
C22 C11 C9 118.4(2) . . ?
C22 C11 C10 123.7(3) . . ?
C22 C11 C16 112.5(3) . . ?
N1 C12 H12A 109.8 . . ?
N1 C12 H12B 109.8 . . ?
N1 C12 C13 109.3(3) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
O1 C13 C12 112.0(3) . . ?
O1 C13 H13A 109.2 . . ?
O1 C13 H13B 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O1 C14 H14A 109.4 . . ?
O1 C14 H14B 109.4 . . ?
O1 C14 C15 111.1(3) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
N1 C15 C14 110.5(3) . . ?
N1 C15 H15A 109.6 . . ?
N1 C15 H15B 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C11 123.3(3) . . ?
C17 C16 C21 118.2(3) . . ?
C21 C16 C11 118.4(3) . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.3(4) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.7(3) . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C11 121.6(3) . . ?
C27 C22 C11 122.1(3) . . ?
C27 C22 C23 116.0(3) . . ?
C22 C23 Br01 121.0(2) . . ?
C24 C23 Br01 116.3(3) . . ?
C24 C23 C22 122.7(3) . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.9(3) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 120.4 . . ?
C26 C25 C24 119.2(3) . . ?
C26 C25 H25 120.4 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.3(4) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 H27 119.1 . . ?
C26 C27 C22 121.9(3) . . ?
C26 C27 H27 119.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
