# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1882145'
loop_
_audit_author_name
_audit_author_address
wenfeng
;wenfeng
?land Islands
;
_audit_update_record             
;
2018-11-29 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H29 Br N2 O4 S'
_chemical_formula_weight         737.64

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)   '

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

_cell_length_a                   9.462(2)
_cell_length_b                   14.849(4)
_cell_length_c                   14.515(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.674(5)
_cell_angle_gamma                90.00
_cell_volume                     1932.0(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1428
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      17.70

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             756
_exptl_absorpt_coefficient_mu    1.160
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_T_max  0.775
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9798
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0964
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4725
_reflns_number_gt                2488
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0500P)²+2.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_number_reflns         4725
_refine_ls_number_parameters     439
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.1943
_refine_ls_wR_factor_gt          0.1764
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.077
_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
C37 C 1.1118(9) 0.5425(4) 0.7610(7) 0.076(3) Uani 1 1 d GD . .
C38 C 1.0748(9) 0.5002(6) 0.6710(5) 0.102(4) Uani 1 1 d GD . .
H38A H 1.0283 0.5326 0.6145 0.123 Uiso 1 1 calc R . .
C39 C 1.1071(10) 0.4095(6) 0.6652(7) 0.119(5) Uani 1 1 d GD . .
H39A H 1.0823 0.3812 0.6050 0.143 Uiso 1 1 calc R . .
C40 C 1.1765(12) 0.3610(4) 0.7496(9) 0.141(6) Uani 1 1 d GD . .
H40A H 1.1982 0.3003 0.7458 0.169 Uiso 1 1 calc R . .
C41 C 1.2136(13) 0.4033(7) 0.8396(7) 0.191(9) Uani 1 1 d GD . .
H41A H 1.2601 0.3709 0.8960 0.229 Uiso 1 1 calc R . .
C42 C 1.1813(12) 0.4941(7) 0.8453(5) 0.170(8) Uani 1 1 d GD . .
H42A H 1.2061 0.5224 0.9056 0.204 Uiso 1 1 calc R . .
S1 S 0.5075(3) 0.6999(2) 0.56507(19) 0.0744(7) Uani 1 1 d . . .
Br1 Br 0.50577(18) 1.20561(11) 0.83509(13) 0.1440(7) Uani 1 1 d . . .
N1 N 0.9326(8) 0.7641(5) 0.6993(6) 0.062(2) Uani 1 1 d . . .
N2 N 0.9557(8) 0.6699(5) 0.7051(6) 0.057(2) Uani 1 1 d . . .
H2B H 0.8897 0.6335 0.6699 0.068 Uiso 1 1 calc R . .
O1 O 0.3835(8) 0.6448(5) 0.5608(6) 0.094(2) Uani 1 1 d . . .
O2 O 0.6451(8) 0.6588(5) 0.5749(5) 0.092(2) Uani 1 1 d . . .
O3 O 0.5330(6) 0.7707(5) 0.6510(5) 0.0687(18) Uani 1 1 d . . .
O4 O 1.1754(8) 0.6867(5) 0.8267(5) 0.090(2) Uani 1 1 d . . .
C1 C 0.6065(14) 1.1056(8) 0.8019(11) 0.084(4) Uani 1 1 d . . .
C2 C 0.5699(11) 1.0824(8) 0.7064(11) 0.085(4) Uani 1 1 d . . .
H2A H 0.4965 1.1146 0.6600 0.102 Uiso 1 1 calc R . .
C3 C 0.6402(11) 1.0123(7) 0.6780(8) 0.073(3) Uani 1 1 d . . .
H3A H 0.6118 0.9944 0.6133 0.088 Uiso 1 1 calc R . .
C4 C 0.7545(10) 0.9686(6) 0.7480(8) 0.061(3) Uani 1 1 d . . .
C5 C 0.7890(11) 0.9945(7) 0.8451(8) 0.073(3) Uani 1 1 d . . .
H5A H 0.8642 0.9650 0.8930 0.088 Uiso 1 1 calc R . .
C6 C 0.7125(14) 1.0630(8) 0.8697(9) 0.089(4) Uani 1 1 d . . .
H6A H 0.7351 1.0799 0.9345 0.107 Uiso 1 1 calc R . .
C7 C 0.8449(8) 0.8971(6) 0.7195(6) 0.051(2) Uani 1 1 d . . .
C8 C 0.9466(8) 0.9089(6) 0.6664(6) 0.050(2) Uani 1 1 d . . .
C9 C 0.9982(9) 0.8224(6) 0.6561(6) 0.052(2) Uani 1 1 d . . .
C10 C 1.1055(10) 0.8054(7) 0.6096(7) 0.067(3) Uani 1 1 d . . .
H10A H 1.1359 0.7469 0.6029 0.081 Uiso 1 1 calc R . .
C11 C 1.1622(9) 0.8750(8) 0.5757(7) 0.069(3) Uani 1 1 d . . .
H11A H 1.2303 0.8646 0.5427 0.083 Uiso 1 1 calc R . .
C12 C 1.1204(9) 0.9659(7) 0.5890(7) 0.057(2) Uani 1 1 d . . .
C13 C 1.0078(8) 0.9832(7) 0.6312(6) 0.053(2) Uani 1 1 d . . .
C14 C 0.9681(10) 1.0733(6) 0.6403(7) 0.062(2) Uani 1 1 d . . .
H14A H 0.8930 1.0858 0.6670 0.074 Uiso 1 1 calc R . .
C15 C 1.0366(11) 1.1418(7) 0.6112(7) 0.075(3) Uani 1 1 d . . .
H15A H 1.0122 1.2009 0.6206 0.091 Uiso 1 1 calc R . .
C16 C 1.1456(11) 1.1237(8) 0.5664(7) 0.074(3) Uani 1 1 d . . .
H16A H 1.1898 1.1711 0.5439 0.088 Uiso 1 1 calc R . .
C17 C 1.1848(10) 1.0412(8) 0.5561(7) 0.073(3) Uani 1 1 d . . .
H17A H 1.2571 1.0311 0.5264 0.088 Uiso 1 1 calc R . .
C18 C 0.8384(9) 0.8083(6) 0.7394(7) 0.058(2) Uani 1 1 d . . .
C19 C 0.7469(10) 0.7604(6) 0.7899(7) 0.061(2) Uani 1 1 d . . .
C20 C 0.6012(10) 0.7384(7) 0.7469(7) 0.062(3) Uani 1 1 d . . .
C21 C 0.5159(12) 0.6955(9) 0.7933(9) 0.089(3) Uani 1 1 d . . .
H21A H 0.4171 0.6808 0.7602 0.107 Uiso 1 1 calc R . .
C22 C 0.5788(17) 0.6745(8) 0.8902(10) 0.099(4) Uani 1 1 d . . .
H22A H 0.5184 0.6502 0.9233 0.119 Uiso 1 1 calc R . .
C23 C 0.7244(14) 0.6877(8) 0.9389(9) 0.081(3) Uani 1 1 d . . .
C24 C 0.8097(12) 0.7366(7) 0.8922(8) 0.076(3) Uani 1 1 d . . .
C25 C 0.9624(13) 0.7578(9) 0.9455(8) 0.088(3) Uani 1 1 d . . .
H25A H 1.0208 0.7882 0.9148 0.106 Uiso 1 1 calc R . .
C26 C 1.0202(16) 0.7342(10) 1.0379(10) 0.114(5) Uani 1 1 d . . .
H26A H 1.1180 0.7495 1.0727 0.137 Uiso 1 1 calc R . .
C27 C 0.932(2) 0.6853(12) 1.0837(10) 0.128(6) Uani 1 1 d . . .
H27A H 0.9758 0.6662 1.1476 0.154 Uiso 1 1 calc R . .
C28 C 0.787(2) 0.6658(10) 1.0374(11) 0.120(5) Uani 1 1 d . . .
H28A H 0.7300 0.6381 1.0706 0.144 Uiso 1 1 calc R . .
C29 C 0.4635(11) 0.7776(7) 0.4709(7) 0.064(3) Uani 1 1 d . . .
C30 C 0.3287(15) 0.7732(10) 0.4030(9) 0.094(4) Uani 1 1 d . . .
H30A H 0.2600 0.7294 0.4060 0.113 Uiso 1 1 calc R . .
C31 C 0.2953(18) 0.8350(13) 0.3293(12) 0.120(5) Uani 1 1 d . . .
H31A H 0.2020 0.8315 0.2821 0.144 Uiso 1 1 calc R . .
C32 C 0.390(3) 0.9018(13) 0.3204(12) 0.126(5) Uani 1 1 d U . .
C33 C 0.5181(19) 0.9014(10) 0.3900(13) 0.108(4) Uani 1 1 d . . .
H33A H 0.5863 0.9463 0.3893 0.130 Uiso 1 1 calc R . .
C34 C 0.5592(14) 0.8397(10) 0.4637(10) 0.093(4) Uani 1 1 d . . .
H34A H 0.6545 0.8415 0.5087 0.112 Uiso 1 1 calc R . .
C35 C 0.349(2) 0.9686(12) 0.2361(12) 0.173(7) Uani 1 1 d U . .
H35A H 0.4296 1.0103 0.2444 0.259 Uiso 1 1 calc R . .
H35B H 0.2606 1.0008 0.2350 0.259 Uiso 1 1 calc R . .
H35C H 0.3313 0.9366 0.1760 0.259 Uiso 1 1 calc R . .
C36 C 1.0856(11) 0.6390(7) 0.7683(8) 0.064(3) 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
C37 C38 1.3900 . ?
C37 C42 1.3900 . ?
C37 C36 1.463(12) . ?
C38 C39 1.3900 . ?
C38 H38A 0.9300 . ?
C39 C40 1.3900 . ?
C39 H39A 0.9300 . ?
C40 C41 1.3900 . ?
C40 H40A 0.9300 . ?
C41 C42 1.3900 . ?
C41 H41A 0.9300 . ?
C42 H42A 0.9300 . ?
S1 O2 1.404(7) . ?
S1 O1 1.415(7) . ?
S1 O3 1.590(6) . ?
S1 C29 1.735(11) . ?
Br1 C1 1.908(11) . ?
N1 C9 1.333(11) . ?
N1 C18 1.377(10) . ?
N1 N2 1.414(10) . ?
N2 C36 1.357(11) . ?
N2 H2B 0.8600 . ?
O3 C20 1.417(10) . ?
O4 C36 1.217(10) . ?
C1 C6 1.320(15) . ?
C1 C2 1.362(15) . ?
C2 C3 1.367(15) . ?
C2 H2A 0.9300 . ?
C3 C4 1.386(12) . ?
C3 H3A 0.9300 . ?
C4 C5 1.395(13) . ?
C4 C7 1.502(12) . ?
C5 C6 1.360(14) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C18 1.355(12) . ?
C7 C8 1.423(11) . ?
C8 C9 1.398(12) . ?
C8 C13 1.416(12) . ?
C9 C10 1.410(12) . ?
C10 C11 1.329(13) . ?
C10 H10A 0.9300 . ?
C11 C12 1.438(13) . ?
C11 H11A 0.9300 . ?
C12 C13 1.411(11) . ?
C12 C17 1.427(14) . ?
C13 C14 1.408(12) . ?
C14 C15 1.344(12) . ?
C14 H14A 0.9300 . ?
C15 C16 1.410(13) . ?
C15 H15A 0.9300 . ?
C16 C17 1.302(14) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.483(12) . ?
C19 C20 1.359(12) . ?
C19 C24 1.455(13) . ?
C20 C21 1.364(13) . ?
C21 C22 1.375(15) . ?
C21 H21A 0.9300 . ?
C22 C23 1.346(15) . ?
C22 H22A 0.9300 . ?
C23 C28 1.399(16) . ?
C23 C24 1.411(14) . ?
C24 C25 1.438(15) . ?
C25 C26 1.324(15) . ?
C25 H25A 0.9300 . ?
C26 C27 1.42(2) . ?
C26 H26A 0.9300 . ?
C27 C28 1.352(19) . ?
C27 H27A 0.9300 . ?
C28 H28A 0.9300 . ?
C29 C34 1.320(14) . ?
C29 C30 1.340(14) . ?
C30 C31 1.368(18) . ?
C30 H30A 0.9300 . ?
C31 C32 1.37(2) . ?
C31 H31A 0.9300 . ?
C32 C33 1.306(19) . ?
C32 C35 1.52(2) . ?
C33 C34 1.366(17) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 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
C38 C37 C42 120.0 . . ?
C38 C37 C36 120.9(8) . . ?
C42 C37 C36 119.1(8) . . ?
C37 C38 C39 120.0 . . ?
C37 C38 H38A 120.0 . . ?
C39 C38 H38A 120.0 . . ?
C40 C39 C38 120.0 . . ?
C40 C39 H39A 120.0 . . ?
C38 C39 H39A 120.0 . . ?
C39 C40 C41 120.0 . . ?
C39 C40 H40A 120.0 . . ?
C41 C40 H40A 120.0 . . ?
C40 C41 C42 120.0 . . ?
C40 C41 H41A 120.0 . . ?
C42 C41 H41A 120.0 . . ?
C41 C42 C37 120.0 . . ?
C41 C42 H42A 120.0 . . ?
C37 C42 H42A 120.0 . . ?
O2 S1 O1 118.8(5) . . ?
O2 S1 O3 107.8(4) . . ?
O1 S1 O3 109.4(4) . . ?
O2 S1 C29 110.5(5) . . ?
O1 S1 C29 111.3(5) . . ?
O3 S1 C29 96.7(4) . . ?
C9 N1 C18 110.5(8) . . ?
C9 N1 N2 125.7(8) . . ?
C18 N1 N2 123.7(8) . . ?
C36 N2 N1 117.7(8) . . ?
C36 N2 H2B 121.1 . . ?
N1 N2 H2B 121.1 . . ?
C20 O3 S1 117.0(6) . . ?
C6 C1 C2 121.5(10) . . ?
C6 C1 Br1 120.5(10) . . ?
C2 C1 Br1 118.0(11) . . ?
C1 C2 C3 120.6(11) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 C4 118.5(11) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
C3 C4 C5 119.1(9) . . ?
C3 C4 C7 120.6(9) . . ?
C5 C4 C7 120.3(9) . . ?
C6 C5 C4 120.0(10) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C1 C6 C5 120.3(11) . . ?
C1 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C18 C7 C8 108.7(8) . . ?
C18 C7 C4 124.0(8) . . ?
C8 C7 C4 127.3(8) . . ?
C9 C8 C13 118.7(7) . . ?
C9 C8 C7 105.3(8) . . ?
C13 C8 C7 135.8(8) . . ?
N1 C9 C8 108.4(7) . . ?
N1 C9 C10 128.6(9) . . ?
C8 C9 C10 123.0(9) . . ?
C11 C10 C9 118.4(9) . . ?
C11 C10 H10A 120.8 . . ?
C9 C10 H10A 120.8 . . ?
C10 C11 C12 121.3(8) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C13 C12 C17 117.7(9) . . ?
C13 C12 C11 120.5(9) . . ?
C17 C12 C11 121.7(9) . . ?
C14 C13 C12 118.3(8) . . ?
C14 C13 C8 123.7(8) . . ?
C12 C13 C8 117.9(8) . . ?
C15 C14 C13 121.3(8) . . ?
C15 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 . . ?
C14 C15 C16 119.9(9) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C17 C16 C15 120.6(10) . . ?
C17 C16 H16A 119.7 . . ?
C15 C16 H16A 119.7 . . ?
C16 C17 C12 122.1(9) . . ?
C16 C17 H17A 119.0 . . ?
C12 C17 H17A 119.0 . . ?
C7 C18 N1 107.1(8) . . ?
C7 C18 C19 130.2(8) . . ?
N1 C18 C19 122.6(8) . . ?
C20 C19 C24 115.7(8) . . ?
C20 C19 C18 123.7(9) . . ?
C24 C19 C18 120.6(9) . . ?
C19 C20 C21 124.0(10) . . ?
C19 C20 O3 116.5(8) . . ?
C21 C20 O3 119.2(9) . . ?
C20 C21 C22 118.7(10) . . ?
C20 C21 H21A 120.6 . . ?
C22 C21 H21A 120.6 . . ?
C23 C22 C21 122.6(10) . . ?
C23 C22 H22A 118.7 . . ?
C21 C22 H22A 118.7 . . ?
C22 C23 C28 122.2(13) . . ?
C22 C23 C24 118.0(10) . . ?
C28 C23 C24 119.2(13) . . ?
C23 C24 C25 119.0(10) . . ?
C23 C24 C19 120.4(10) . . ?
C25 C24 C19 120.5(9) . . ?
C26 C25 C24 120.3(12) . . ?
C26 C25 H25A 119.8 . . ?
C24 C25 H25A 119.8 . . ?
C25 C26 C27 119.8(14) . . ?
C25 C26 H26A 120.1 . . ?
C27 C26 H26A 120.1 . . ?
C28 C27 C26 122.0(13) . . ?
C28 C27 H27A 119.0 . . ?
C26 C27 H27A 119.0 . . ?
C27 C28 C23 119.4(14) . . ?
C27 C28 H28A 120.3 . . ?
C23 C28 H28A 120.3 . . ?
C34 C29 C30 119.4(12) . . ?
C34 C29 S1 122.0(10) . . ?
C30 C29 S1 118.6(10) . . ?
C29 C30 C31 118.0(14) . . ?
C29 C30 H30A 121.0 . . ?
C31 C30 H30A 121.0 . . ?
C30 C31 C32 124.5(16) . . ?
C30 C31 H31A 117.8 . . ?
C32 C31 H31A 117.8 . . ?
C33 C32 C31 113.3(17) . . ?
C33 C32 C35 124(2) . . ?
C31 C32 C35 123(2) . . ?
C32 C33 C34 124.7(15) . . ?
C32 C33 H33A 117.6 . . ?
C34 C33 H33A 117.6 . . ?
C29 C34 C33 120.0(12) . . ?
C29 C34 H34A 120.0 . . ?
C33 C34 H34A 120.0 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O4 C36 N2 123.5(9) . . ?
O4 C36 C37 121.6(9) . . ?
N2 C36 C37 114.9(9) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.870
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_xb1852
_database_code_depnum_ccdc_archive 'CCDC 1891943'
loop_
_audit_author_name
_audit_author_address
'yulong hu'
;northwest university
China
;
_audit_update_record             
;
2019-01-19 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-01-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H27 Br N2 O2, C3 H8 O'
_chemical_formula_sum            'C39 H35 Br N2 O3'
_chemical_formula_weight         659.60
_chemical_absolute_configuration rm
_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 0.0033 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'

_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                   11.153(2)
_cell_length_b                   11.570(2)
_cell_length_c                   25.918(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3344.4(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2717
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.497
_cell_measurement_theta_min      2.359
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    1.269
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0929 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.6888. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0949
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18279
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.339
_diffrn_reflns_theta_min         1.571
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                3530
_reflns_number_total             6740
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.719
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1122 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         6740
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1314
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²+0.3433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1773
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C39) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2B), C37(H37)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27),
  C28(H28), C32(H32), C33(H33), C34(H34), C35(H35)
3.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_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
Br1 Br 1.04727(14) 0.31332(14) 0.58137(7) 0.1838(8) Uani 1 1 d . . . . .
O1 O 0.3684(5) 0.6283(5) 0.79231(17) 0.0816(15) Uani 1 1 d . . . . .
O2 O 0.2946(4) 0.5939(4) 0.67829(19) 0.0714(13) Uani 1 1 d . . . . .
H2 H 0.352418 0.600169 0.697658 0.107 Uiso 1 1 calc GR . . . .
N1 N 0.4999(4) 0.6879(4) 0.70900(17) 0.0470(12) Uani 1 1 d . . . . .
N2 N 0.5041(4) 0.7491(4) 0.75684(17) 0.0494(12) Uani 1 1 d . . . . .
H2A H 0.548819 0.809129 0.760415 0.059 Uiso 1 1 calc R . . . .
C1 C 0.4827(5) 0.7651(5) 0.66332(19) 0.0435(14) Uani 1 1 d . . . . .
H1 H 0.519857 0.840134 0.670642 0.052 Uiso 1 1 calc R . . . .
C2 C 0.5555(5) 0.7040(5) 0.6195(2) 0.0480(15) Uani 1 1 d . . . . .
H2B H 0.500415 0.656237 0.599163 0.058 Uiso 1 1 calc R . . . .
C3 C 0.6375(5) 0.6255(5) 0.6498(2) 0.0461(14) Uani 1 1 d . . . . .
C4 C 0.7332(6) 0.5559(6) 0.6318(2) 0.0558(16) Uani 1 1 d . . . . .
C5 C 0.7751(6) 0.5543(6) 0.5797(3) 0.0633(18) Uani 1 1 d . . . . .
H5 H 0.739810 0.602064 0.555126 0.076 Uiso 1 1 calc R . . . .
C6 C 0.8666(8) 0.4829(8) 0.5661(3) 0.090(3) Uani 1 1 d . . . . .
H6 H 0.893017 0.481971 0.532064 0.108 Uiso 1 1 calc R . . . .
C7 C 0.9208(8) 0.4120(8) 0.6018(4) 0.093(3) Uani 1 1 d . . . . .
C8 C 0.8843(7) 0.4079(7) 0.6514(4) 0.087(2) Uani 1 1 d . . . . .
H8 H 0.921255 0.357810 0.674502 0.104 Uiso 1 1 calc R . . . .
C9 C 0.7894(6) 0.4801(6) 0.6682(3) 0.0600(17) Uani 1 1 d . . . . .
C10 C 0.7465(6) 0.4760(6) 0.7197(3) 0.0629(19) Uani 1 1 d . . . . .
H10 H 0.782122 0.425539 0.743073 0.075 Uiso 1 1 calc R . . . .
C11 C 0.6552(6) 0.5439(5) 0.7355(2) 0.0557(17) Uani 1 1 d . . . . .
H11 H 0.627873 0.540745 0.769394 0.067 Uiso 1 1 calc R . . . .
C12 C 0.6025(5) 0.6192(5) 0.6998(2) 0.0475(15) Uani 1 1 d . . . . .
C13 C 0.4364(6) 0.7104(6) 0.7961(2) 0.0545(16) Uani 1 1 d . . . . .
C14 C 0.4538(6) 0.7718(6) 0.8465(2) 0.0539(15) Uani 1 1 d . . . . .
C15 C 0.3753(7) 0.7439(7) 0.8864(2) 0.073(2) Uani 1 1 d . . . . .
H15 H 0.314206 0.690872 0.880432 0.088 Uiso 1 1 calc R . . . .
C16 C 0.3864(9) 0.7930(8) 0.9340(3) 0.092(3) Uani 1 1 d . . . . .
H16 H 0.331975 0.775235 0.959971 0.111 Uiso 1 1 calc R . . . .
C17 C 0.4778(9) 0.8680(8) 0.9431(3) 0.091(3) Uani 1 1 d . . . . .
H17 H 0.486841 0.899019 0.975937 0.109 Uiso 1 1 calc R . . . .
C18 C 0.5579(8) 0.8995(7) 0.9046(3) 0.082(2) Uani 1 1 d . . . . .
H18 H 0.619128 0.952091 0.911084 0.098 Uiso 1 1 calc R . . . .
C19 C 0.5440(7) 0.8504(6) 0.8560(2) 0.0638(18) Uani 1 1 d . . . . .
H19 H 0.596259 0.870856 0.829510 0.077 Uiso 1 1 calc R . . . .
C20 C 0.3518(5) 0.7842(5) 0.6501(2) 0.0472(14) Uani 1 1 d . . . . .
C21 C 0.2679(5) 0.6991(6) 0.6576(2) 0.0559(16) Uani 1 1 d . . . . .
C22 C 0.1472(6) 0.7145(7) 0.6437(3) 0.0708(19) Uani 1 1 d . . . . .
H22 H 0.091629 0.656490 0.650420 0.085 Uiso 1 1 calc R . . . .
C23 C 0.1119(6) 0.8132(8) 0.6205(3) 0.078(2) Uani 1 1 d . . . . .
H23 H 0.031667 0.822692 0.611661 0.094 Uiso 1 1 calc R . . . .
C24 C 0.1947(6) 0.9028(7) 0.6094(2) 0.0625(18) Uani 1 1 d . . . . .
C25 C 0.1601(8) 1.0023(9) 0.5818(3) 0.095(3) Uani 1 1 d . . . . .
H25 H 0.080580 1.010798 0.571688 0.114 Uiso 1 1 calc R . . . .
C26 C 0.2401(8) 1.0851(8) 0.5700(3) 0.087(2) Uani 1 1 d . . . . .
H26 H 0.215800 1.149700 0.551335 0.104 Uiso 1 1 calc R . . . .
C27 C 0.3603(7) 1.0745(6) 0.5856(3) 0.072(2) Uani 1 1 d . . . . .
H27 H 0.415488 1.131856 0.577433 0.087 Uiso 1 1 calc R . . . .
C28 C 0.3957(6) 0.9793(5) 0.6130(2) 0.0556(17) Uani 1 1 d . . . . .
H28 H 0.474882 0.973843 0.623883 0.067 Uiso 1 1 calc R . . . .
C29 C 0.3159(5) 0.8901(6) 0.6249(2) 0.0515(16) Uani 1 1 d . . . . .
C30 C 0.6150(5) 0.7914(5) 0.5837(2) 0.0512(15) Uani 1 1 d . . . . .
C31 C 0.5753(6) 0.8065(6) 0.5330(2) 0.0641(18) Uani 1 1 d . . . . .
C32 C 0.6342(8) 0.8914(7) 0.5037(3) 0.082(2) Uani 1 1 d . . . . .
H32 H 0.609649 0.903037 0.469810 0.099 Uiso 1 1 calc R . . . .
C33 C 0.7251(8) 0.9573(7) 0.5223(4) 0.083(2) Uani 1 1 d . . . . .
H33 H 0.761505 1.012354 0.501350 0.100 Uiso 1 1 calc R . . . .
C34 C 0.7631(7) 0.9419(7) 0.5724(4) 0.078(2) Uani 1 1 d . . . . .
H34 H 0.824058 0.987694 0.585850 0.094 Uiso 1 1 calc R . . . .
C35 C 0.7095(5) 0.8576(6) 0.6026(3) 0.0609(17) Uani 1 1 d . . . . .
H35 H 0.737197 0.844989 0.635986 0.073 Uiso 1 1 calc R . . . .
C36 C 0.4742(8) 0.7382(9) 0.5109(3) 0.091(3) Uani 1 1 d . . . . .
H36A H 0.493175 0.657390 0.512531 0.136 Uiso 1 1 calc GR . . . .
H36B H 0.461778 0.760451 0.475662 0.136 Uiso 1 1 calc GR . . . .
H36C H 0.402608 0.752945 0.530424 0.136 Uiso 1 1 calc GR . . . .
O3 O 0.2935(4) 0.4014(4) 0.76166(18) 0.0675(12) Uani 1 1 d . . . . .
H3 H 0.311107 0.467037 0.770924 0.101 Uiso 1 1 calc GR . . . .
C37 C 0.1689(7) 0.3977(7) 0.7475(3) 0.084(2) Uani 1 1 d . . . . .
H37 H 0.164826 0.419455 0.711028 0.101 Uiso 1 1 calc R . . . .
C38 C 0.0951(8) 0.4813(10) 0.7755(4) 0.123(4) Uani 1 1 d . . . . .
H38A H 0.105304 0.470311 0.811958 0.185 Uiso 1 1 calc GR . . . .
H38B H 0.012336 0.470241 0.766592 0.185 Uiso 1 1 calc GR . . . .
H38C H 0.119173 0.558292 0.766347 0.185 Uiso 1 1 calc GR . . . .
C39 C 0.1286(10) 0.2776(9) 0.7506(5) 0.142(4) Uani 1 1 d . U . . .
H39A H 0.168821 0.232623 0.724790 0.213 Uiso 1 1 calc GR . . . .
H39B H 0.043601 0.274296 0.745015 0.213 Uiso 1 1 calc GR . . . .
H39C H 0.146949 0.247178 0.784184 0.213 Uiso 1 1 calc GR . . . .


_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 C7 1.890(7) . ?
O1 C13 1.220(8) . ?
O2 H2 0.8200 . ?
O2 C21 1.363(8) . ?
N1 N2 1.428(6) . ?
N1 C1 1.495(7) . ?
N1 C12 1.414(7) . ?
N2 H2A 0.8600 . ?
N2 C13 1.344(8) . ?
C1 H1 0.9800 . ?
C1 C2 1.565(8) . ?
C1 C20 1.516(8) . ?
C2 H2B 0.9800 . ?
C2 C3 1.509(8) . ?
C2 C30 1.524(8) . ?
C3 C4 1.416(8) . ?
C3 C12 1.356(8) . ?
C4 C5 1.429(9) . ?
C4 C9 1.432(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.360(10) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(12) . ?
C7 C8 1.350(12) . ?
C8 H8 0.9300 . ?
C8 C9 1.417(9) . ?
C9 C10 1.420(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.350(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.401(8) . ?
C13 C14 1.500(8) . ?
C14 C15 1.392(9) . ?
C14 C19 1.378(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.363(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.359(12) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(11) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(8) . ?
C20 C29 1.445(8) . ?
C21 C22 1.405(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.350(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.417(10) . ?
C24 C25 1.409(11) . ?
C24 C29 1.418(9) . ?
C25 H25 0.9300 . ?
C25 C26 1.346(12) . ?
C26 H26 0.9300 . ?
C26 C27 1.406(11) . ?
C27 H27 0.9300 . ?
C27 C28 1.367(9) . ?
C28 H28 0.9300 . ?
C28 C29 1.398(9) . ?
C30 C31 1.397(8) . ?
C30 C35 1.392(9) . ?
C31 C32 1.405(10) . ?
C31 C36 1.491(11) . ?
C32 H32 0.9300 . ?
C32 C33 1.356(11) . ?
C33 H33 0.9300 . ?
C33 C34 1.378(12) . ?
C34 H34 0.9300 . ?
C34 C35 1.386(10) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O3 H3 0.8200 . ?
O3 C37 1.438(8) . ?
C37 H37 0.9800 . ?
C37 C38 1.463(12) . ?
C37 C39 1.462(11) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 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
C21 O2 H2 109.5 . . ?
N2 N1 C1 113.3(4) . . ?
C12 N1 N2 113.5(4) . . ?
C12 N1 C1 107.8(4) . . ?
N1 N2 H2A 120.9 . . ?
C13 N2 N1 118.3(5) . . ?
C13 N2 H2A 120.9 . . ?
N1 C1 H1 108.8 . . ?
N1 C1 C2 103.8(4) . . ?
N1 C1 C20 112.9(5) . . ?
C2 C1 H1 108.8 . . ?
C20 C1 H1 108.8 . . ?
C20 C1 C2 113.6(4) . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 C1 102.1(4) . . ?
C3 C2 H2B 108.7 . . ?
C3 C2 C30 116.9(5) . . ?
C30 C2 C1 111.6(5) . . ?
C30 C2 H2B 108.7 . . ?
C4 C3 C2 128.9(5) . . ?
C12 C3 C2 110.8(5) . . ?
C12 C3 C4 120.1(5) . . ?
C3 C4 C5 124.4(6) . . ?
C3 C4 C9 117.5(6) . . ?
C5 C4 C9 118.1(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.9(7) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(7) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 Br1 120.0(7) . . ?
C8 C7 Br1 118.1(7) . . ?
C8 C7 C6 121.9(7) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(8) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 119.1(7) . . ?
C8 C9 C10 121.4(7) . . ?
C10 C9 C4 119.5(6) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.3(6) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.5(6) . . ?
C12 C11 H11 120.7 . . ?
C3 C12 N1 111.4(5) . . ?
C3 C12 C11 123.0(6) . . ?
C11 C12 N1 125.3(5) . . ?
O1 C13 N2 123.2(6) . . ?
O1 C13 C14 121.3(6) . . ?
N2 C13 C14 115.4(6) . . ?
C15 C14 C13 117.1(6) . . ?
C19 C14 C13 124.2(6) . . ?
C19 C14 C15 118.7(6) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(8) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.4(8) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.7(7) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 120.9 . . ?
C17 C18 C19 118.2(8) . . ?
C19 C18 H18 120.9 . . ?
C14 C19 C18 120.8(7) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C1 121.4(5) . . ?
C21 C20 C29 118.9(5) . . ?
C29 C20 C1 119.5(5) . . ?
O2 C21 C20 123.2(5) . . ?
O2 C21 C22 115.0(6) . . ?
C20 C21 C22 121.8(6) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.1(7) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.2(6) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C29 119.2(6) . . ?
C25 C24 C23 121.4(7) . . ?
C25 C24 C29 119.3(8) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.1(8) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.3(8) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 120.2 . . ?
C28 C27 C26 119.7(8) . . ?
C28 C27 H27 120.2 . . ?
C27 C28 H28 119.1 . . ?
C27 C28 C29 121.7(7) . . ?
C29 C28 H28 119.1 . . ?
C24 C29 C20 118.7(6) . . ?
C28 C29 C20 123.4(5) . . ?
C28 C29 C24 117.9(6) . . ?
C31 C30 C2 121.1(6) . . ?
C35 C30 C2 118.7(5) . . ?
C35 C30 C31 120.1(6) . . ?
C30 C31 C32 116.6(7) . . ?
C30 C31 C36 122.3(6) . . ?
C32 C31 C36 121.1(7) . . ?
C31 C32 H32 118.3 . . ?
C33 C32 C31 123.4(7) . . ?
C33 C32 H32 118.3 . . ?
C32 C33 H33 120.3 . . ?
C32 C33 C34 119.4(7) . . ?
C34 C33 H33 120.3 . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.4(8) . . ?
C35 C34 H34 120.3 . . ?
C30 C35 H35 119.5 . . ?
C34 C35 C30 121.0(7) . . ?
C34 C35 H35 119.5 . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C37 O3 H3 109.5 . . ?
O3 C37 H37 106.4 . . ?
O3 C37 C38 113.5(7) . . ?
O3 C37 C39 108.1(7) . . ?
C38 C37 H37 106.4 . . ?
C38 C37 C39 115.3(9) . . ?
C39 C37 H37 106.4 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 N1 0.82 1.95 2.656(6) 143.0 . yes
O3 H3 O1 0.82 2.05 2.867(7) 175.6 . yes

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
Br1 C7 C8 C9 -179.7(6) . . . . ?
O1 C13 C14 C15 -10.2(10) . . . . ?
O1 C13 C14 C19 167.6(6) . . . . ?
O2 C21 C22 C23 -176.7(6) . . . . ?
N1 N2 C13 O1 -2.8(9) . . . . ?
N1 N2 C13 C14 174.5(5) . . . . ?
N1 C1 C2 C3 -18.9(5) . . . . ?
N1 C1 C2 C30 -144.4(5) . . . . ?
N1 C1 C20 C21 -33.5(8) . . . . ?
N1 C1 C20 C29 152.1(5) . . . . ?
N2 N1 C1 C2 146.3(4) . . . . ?
N2 N1 C1 C20 -90.2(5) . . . . ?
N2 N1 C12 C3 -139.4(5) . . . . ?
N2 N1 C12 C11 47.1(8) . . . . ?
N2 C13 C14 C15 172.4(6) . . . . ?
N2 C13 C14 C19 -9.7(9) . . . . ?
C1 N1 N2 C13 131.8(5) . . . . ?
C1 N1 C12 C3 -13.1(6) . . . . ?
C1 N1 C12 C11 173.4(6) . . . . ?
C1 C2 C3 C4 -173.2(6) . . . . ?
C1 C2 C3 C12 12.4(6) . . . . ?
C1 C2 C30 C31 -110.0(6) . . . . ?
C1 C2 C30 C35 69.3(6) . . . . ?
C1 C20 C21 O2 1.6(9) . . . . ?
C1 C20 C21 C22 -177.6(6) . . . . ?
C1 C20 C29 C24 175.4(5) . . . . ?
C1 C20 C29 C28 -1.9(8) . . . . ?
C2 C1 C20 C21 84.4(7) . . . . ?
C2 C1 C20 C29 -90.1(6) . . . . ?
C2 C3 C4 C5 4.6(10) . . . . ?
C2 C3 C4 C9 -173.8(6) . . . . ?
C2 C3 C12 N1 -0.1(7) . . . . ?
C2 C3 C12 C11 173.6(6) . . . . ?
C2 C30 C31 C32 178.4(6) . . . . ?
C2 C30 C31 C36 -0.5(9) . . . . ?
C2 C30 C35 C34 -177.0(6) . . . . ?
C3 C2 C30 C31 133.2(6) . . . . ?
C3 C2 C30 C35 -47.5(7) . . . . ?
C3 C4 C5 C6 -179.0(7) . . . . ?
C3 C4 C9 C8 179.1(6) . . . . ?
C3 C4 C9 C10 1.1(9) . . . . ?
C4 C3 C12 N1 -175.1(5) . . . . ?
C4 C3 C12 C11 -1.4(9) . . . . ?
C4 C5 C6 C7 -0.4(12) . . . . ?
C4 C9 C10 C11 -1.3(10) . . . . ?
C5 C4 C9 C8 0.6(9) . . . . ?
C5 C4 C9 C10 -177.4(6) . . . . ?
C5 C6 C7 Br1 179.7(6) . . . . ?
C5 C6 C7 C8 1.6(15) . . . . ?
C6 C7 C8 C9 -1.6(14) . . . . ?
C7 C8 C9 C4 0.5(11) . . . . ?
C7 C8 C9 C10 178.4(8) . . . . ?
C8 C9 C10 C11 -179.2(7) . . . . ?
C9 C4 C5 C6 -0.6(10) . . . . ?
C9 C10 C11 C12 0.2(10) . . . . ?
C10 C11 C12 N1 174.1(6) . . . . ?
C10 C11 C12 C3 1.3(9) . . . . ?
C12 N1 N2 C13 -104.8(6) . . . . ?
C12 N1 C1 C2 19.9(6) . . . . ?
C12 N1 C1 C20 143.4(5) . . . . ?
C12 C3 C4 C5 178.6(6) . . . . ?
C12 C3 C4 C9 0.2(9) . . . . ?
C13 C14 C15 C16 178.1(7) . . . . ?
C13 C14 C19 C18 -176.8(6) . . . . ?
C14 C15 C16 C17 -1.9(12) . . . . ?
C15 C14 C19 C18 1.1(10) . . . . ?
C15 C16 C17 C18 2.4(13) . . . . ?
C16 C17 C18 C19 -1.2(12) . . . . ?
C17 C18 C19 C14 -0.6(11) . . . . ?
C19 C14 C15 C16 0.1(11) . . . . ?
C20 C1 C2 C3 -141.9(5) . . . . ?
C20 C1 C2 C30 92.6(6) . . . . ?
C20 C21 C22 C23 2.5(10) . . . . ?
C21 C20 C29 C24 0.8(8) . . . . ?
C21 C20 C29 C28 -176.5(5) . . . . ?
C21 C22 C23 C24 0.4(11) . . . . ?
C22 C23 C24 C25 175.2(7) . . . . ?
C22 C23 C24 C29 -2.6(10) . . . . ?
C23 C24 C25 C26 -177.8(8) . . . . ?
C23 C24 C29 C20 1.9(9) . . . . ?
C23 C24 C29 C28 179.4(6) . . . . ?
C24 C25 C26 C27 -0.9(13) . . . . ?
C25 C24 C29 C20 -175.9(6) . . . . ?
C25 C24 C29 C28 1.5(9) . . . . ?
C25 C26 C27 C28 0.1(12) . . . . ?
C26 C27 C28 C29 1.6(11) . . . . ?
C27 C28 C29 C20 175.0(6) . . . . ?
C27 C28 C29 C24 -2.3(9) . . . . ?
C29 C20 C21 O2 176.1(5) . . . . ?
C29 C20 C21 C22 -3.0(9) . . . . ?
C29 C24 C25 C26 0.1(12) . . . . ?
C30 C2 C3 C4 -51.3(8) . . . . ?
C30 C2 C3 C12 134.3(5) . . . . ?
C30 C31 C32 C33 -0.2(11) . . . . ?
C31 C30 C35 C34 2.3(9) . . . . ?
C31 C32 C33 C34 -0.1(12) . . . . ?
C32 C33 C34 C35 1.5(11) . . . . ?
C33 C34 C35 C30 -2.6(10) . . . . ?
C35 C30 C31 C32 -0.9(9) . . . . ?
C35 C30 C31 C36 -179.8(7) . . . . ?
C36 C31 C32 C33 178.7(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_xb1989_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 1905131'
loop_
_audit_author_name
_audit_author_address
'yulong hu'
;northwest university
China
;
_audit_update_record             
;
2019-03-26 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-03-26
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C48 H33 Br N2 O4 S'
_chemical_formula_sum            'C48 H33 Br N2 O4 S'
_chemical_formula_weight         813.73
_chemical_absolute_configuration ?
_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 0.0033 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'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   15.033(5)
_cell_length_b                   8.026(2)
_cell_length_c                   18.952(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.392(6)
_cell_angle_gamma                90
_cell_volume                     2282.5(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2071
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.819
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0854 before and 0.0627 after correction. The Ratio of minimum to maximum transmission is 0.8534. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.1003
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11426
_diffrn_reflns_point_group_measured_fraction_full 0.891
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.076
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.769
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                4502
_reflns_number_total             7175
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    ?
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.149
_refine_ls_abs_structure_details 
;
 Flack x determined using 1334 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0640
_refine_ls_restrained_S_all      0.994
_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)+(0.1141P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.2060
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C27(H27), C28(H28),
  C29(H29), C30(H30), C32(H32), C33(H33), C36(H36), C37(H37), C39(H39),
 C40(H40), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
2.b Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Br1 Br 0.88993(6) 0.66608(14) 0.55233(5) 0.0770(4) Uani 1 1 d . . . . .
C1 C 0.6238(5) 0.7269(11) 0.6450(4) 0.049(2) Uani 1 1 d . . . . .
C2 C 0.5676(7) 0.8651(14) 0.6426(5) 0.063(3) Uani 1 1 d . . . . .
H2 H 0.5448 0.9073 0.6835 0.075 Uiso 1 1 calc R . . . .
C3 C 0.5474(6) 0.9350(14) 0.5797(5) 0.061(3) Uani 1 1 d . . . . .
H3 H 0.5100 1.0273 0.5772 0.074 Uiso 1 1 calc R . . . .
C4 C 0.5816(6) 0.8721(12) 0.5165(5) 0.054(2) Uani 1 1 d . . . . .
C5 C 0.6369(5) 0.7286(12) 0.5176(4) 0.049(2) Uani 1 1 d . . . . .
C6 C 0.6603(4) 0.6585(14) 0.5860(4) 0.0448(18) Uani 1 1 d . . . . .
C7 C 0.5591(7) 0.9426(15) 0.4489(5) 0.069(3) Uani 1 1 d . . . . .
H7 H 0.5242 1.0383 0.4464 0.083 Uiso 1 1 calc R . . . .
C8 C 0.5857(7) 0.8775(15) 0.3892(5) 0.068(3) Uani 1 1 d . . . . .
H8 H 0.5686 0.9278 0.3463 0.082 Uiso 1 1 calc R . . . .
C9 C 0.6396(6) 0.7335(13) 0.3897(4) 0.057(3) Uani 1 1 d . . . . .
C10 C 0.6648(5) 0.6626(15) 0.4538(4) 0.051(2) Uani 1 1 d . . . . .
H10 H 0.7012 0.5688 0.4550 0.061 Uiso 1 1 calc R . . . .
C11 C 0.6630(5) 0.656(2) 0.3223(4) 0.068(3) Uani 1 1 d . . . . .
C12 C 0.6804(8) 0.746(2) 0.2628(6) 0.092(4) Uani 1 1 d . . . . .
H12 H 0.6808 0.8614 0.2665 0.110 Uiso 1 1 calc R . . . .
C13 C 0.6965(9) 0.679(3) 0.2005(6) 0.109(5) Uani 1 1 d . . . . .
H13 H 0.7082 0.7462 0.1621 0.131 Uiso 1 1 calc R . . . .
C14 C 0.6955(10) 0.508(3) 0.1945(7) 0.114(6) Uani 1 1 d . . . . .
H14 H 0.7056 0.4604 0.1510 0.137 Uiso 1 1 calc R . . . .
C15 C 0.6797(8) 0.403(2) 0.2523(6) 0.100(4) Uani 1 1 d . . . . .
H15 H 0.6800 0.2879 0.2485 0.120 Uiso 1 1 calc R . . . .
C16 C 0.6633(7) 0.485(2) 0.3158(6) 0.080(4) Uani 1 1 d . . . . .
H16 H 0.6522 0.4208 0.3552 0.097 Uiso 1 1 calc R . . . .
C17 C 0.7148(5) 0.5187(11) 0.6096(4) 0.0422(19) Uani 1 1 d . . . . .
C18 C 0.7654(5) 0.4048(11) 0.5656(4) 0.044(2) Uani 1 1 d . . . . .
C19 C 0.7347(6) 0.2470(13) 0.5507(5) 0.059(2) Uani 1 1 d . . . . .
H19 H 0.6840 0.2103 0.5719 0.070 Uiso 1 1 calc R . . . .
C20 C 0.7757(7) 0.1399(18) 0.5055(6) 0.081(3) Uani 1 1 d . . . . .
H20 H 0.7529 0.0337 0.4966 0.097 Uiso 1 1 calc R . . . .
C21 C 0.8503(7) 0.193(2) 0.4740(6) 0.084(4) Uani 1 1 d . . . . .
H21 H 0.8780 0.1223 0.4431 0.101 Uiso 1 1 calc R . . . .
C22 C 0.8840(7) 0.3455(16) 0.4875(5) 0.069(3) Uani 1 1 d . . . . .
H22 H 0.9351 0.3798 0.4663 0.083 Uiso 1 1 calc R . . . .
C23 C 0.8423(6) 0.4527(12) 0.5335(5) 0.055(2) Uani 1 1 d . . . . .
C24 C 0.7098(6) 0.5090(11) 0.6814(4) 0.046(2) Uani 1 1 d . . . . .
C25 C 0.7538(6) 0.3978(12) 0.7348(4) 0.050(2) Uani 1 1 d . . . . .
C26 C 0.7029(6) 0.2716(12) 0.7683(4) 0.054(2) Uani 1 1 d . . . . .
C27 C 0.6093(7) 0.2479(13) 0.7513(5) 0.063(2) Uani 1 1 d . . . . .
H27 H 0.5817 0.3046 0.7132 0.075 Uiso 1 1 calc R . . . .
C28 C 0.5613(8) 0.1453(16) 0.7897(6) 0.075(3) Uani 1 1 d . . . . .
H28 H 0.5002 0.1358 0.7795 0.090 Uiso 1 1 calc R . . . .
C29 C 0.6011(11) 0.0545(16) 0.8435(7) 0.085(4) Uani 1 1 d . . . . .
H29 H 0.5665 -0.0164 0.8693 0.102 Uiso 1 1 calc R . . . .
C30 C 0.6890(12) 0.0645(16) 0.8604(6) 0.086(4) Uani 1 1 d . . . . .
H30 H 0.7143 0.0001 0.8971 0.103 Uiso 1 1 calc R . . . .
C31 C 0.7427(7) 0.1720(18) 0.8227(4) 0.068(2) Uani 1 1 d . . . . .
C32 C 0.8347(8) 0.1944(16) 0.8397(5) 0.080(3) Uani 1 1 d . . . . .
H32 H 0.8628 0.1258 0.8737 0.096 Uiso 1 1 calc R . . . .
C33 C 0.8825(8) 0.3091(16) 0.8091(6) 0.077(3) Uani 1 1 d . . . . .
H33 H 0.9430 0.3209 0.8211 0.092 Uiso 1 1 calc R . . . .
C34 C 0.8388(7) 0.4139(14) 0.7572(5) 0.063(3) Uani 1 1 d . . . . .
C35 C 0.9503(7) 0.8508(14) 0.7342(6) 0.068(3) Uani 1 1 d . . . . .
C36 C 0.8967(7) 0.9549(18) 0.6935(6) 0.079(3) Uani 1 1 d . . . . .
H36 H 0.8357 0.9352 0.6875 0.094 Uiso 1 1 calc R . . . .
C37 C 0.9343(8) 1.0881(17) 0.6618(6) 0.078(3) Uani 1 1 d . . . . .
H37 H 0.8975 1.1585 0.6342 0.093 Uiso 1 1 calc R . . . .
C38 C 1.0227(8) 1.1229(16) 0.6688(6) 0.079(3) Uani 1 1 d . . . . .
C39 C 1.0753(8) 1.012(2) 0.7079(8) 0.110(5) Uani 1 1 d . . . . .
H39 H 1.1364 1.0299 0.7125 0.132 Uiso 1 1 calc R . . . .
C40 C 1.0405(8) 0.874(2) 0.7403(7) 0.097(4) Uani 1 1 d . . . . .
H40 H 1.0775 0.7998 0.7656 0.116 Uiso 1 1 calc R . . . .
C41 C 1.0658(12) 1.273(2) 0.6382(7) 0.117(5) Uani 1 1 d . . . . .
H41A H 1.0618 1.3652 0.6700 0.176 Uiso 1 1 calc GR . . . .
H41B H 1.0359 1.2999 0.5935 0.176 Uiso 1 1 calc GR . . . .
H41C H 1.1273 1.2489 0.6315 0.176 Uiso 1 1 calc GR . . . .
C42 C 0.5549(7) 0.6196(12) 0.7972(5) 0.057(3) Uani 1 1 d . . . . .
C43 C 0.5528(7) 0.6370(14) 0.8745(4) 0.062(3) Uani 1 1 d . . . . .
C44 C 0.4717(8) 0.667(2) 0.9028(5) 0.083(3) Uani 1 1 d . . . . .
H44 H 0.4196 0.6703 0.8737 0.100 Uiso 1 1 calc R . . . .
C45 C 0.4685(12) 0.694(2) 0.9765(8) 0.113(5) Uani 1 1 d . . . . .
H45 H 0.4146 0.7184 0.9959 0.135 Uiso 1 1 calc R . . . .
C46 C 0.5438(15) 0.683(3) 1.0182(7) 0.137(7) Uani 1 1 d . . . . .
H46 H 0.5413 0.6975 1.0667 0.164 Uiso 1 1 calc R . . . .
C47 C 0.6197(10) 0.654(3) 0.9919(5) 0.123(6) Uani 1 1 d . . . . .
H47 H 0.6706 0.6492 1.0223 0.148 Uiso 1 1 calc R . . . .
C48 C 0.6282(8) 0.628(2) 0.9196(6) 0.093(5) Uani 1 1 d . . . . .
H48 H 0.6835 0.6046 0.9023 0.111 Uiso 1 1 calc R . . . .
N1 N 0.6350(5) 0.6637(14) 0.7717(3) 0.0581(19) Uani 1 1 d . . . . .
H1 H 0.674(6) 0.703(15) 0.798(5) 0.070 Uiso 1 1 d R . . . .
N2 N 0.6535(5) 0.6322(11) 0.7018(3) 0.056(2) Uani 1 1 d . . . . .
O1 O 0.8885(4) 0.5508(10) 0.7308(3) 0.0658(18) Uani 1 1 d . . . . .
O2 O 0.8194(6) 0.7498(13) 0.8078(5) 0.110(3) Uani 1 1 d . . . . .
O3 O 0.9684(6) 0.6483(16) 0.8411(4) 0.121(3) Uani 1 1 d . . . . .
O4 O 0.4922(5) 0.5791(11) 0.7601(4) 0.077(2) Uani 1 1 d . . . . .
S1 S 0.9046(2) 0.6995(5) 0.78691(15) 0.0832(10) 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 C23 1.882(10) . ?
C1 C2 1.394(13) . ?
C1 C6 1.386(11) . ?
C1 N2 1.371(11) . ?
C2 H2 0.9300 . ?
C2 C3 1.335(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.423(13) . ?
C4 C5 1.420(13) . ?
C4 C7 1.424(13) . ?
C5 C6 1.437(11) . ?
C5 C10 1.407(12) . ?
C6 C17 1.444(13) . ?
C7 H7 0.9300 . ?
C7 C8 1.330(15) . ?
C8 H8 0.9300 . ?
C8 C9 1.411(15) . ?
C9 C10 1.374(11) . ?
C9 C11 1.484(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(15) . ?
C11 C16 1.375(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.33(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.38(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.41(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.405(17) . ?
C16 H16 0.9300 . ?
C17 C18 1.478(12) . ?
C17 C24 1.370(11) . ?
C18 C19 1.372(14) . ?
C18 C23 1.393(12) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(15) . ?
C20 H20 0.9300 . ?
C20 C21 1.368(16) . ?
C21 H21 0.9300 . ?
C21 C22 1.346(18) . ?
C22 H22 0.9300 . ?
C22 C23 1.399(14) . ?
C24 C25 1.476(12) . ?
C24 N2 1.372(11) . ?
C25 C26 1.439(13) . ?
C25 C34 1.328(12) . ?
C26 C27 1.438(13) . ?
C26 C31 1.409(13) . ?
C27 H27 0.9300 . ?
C27 C28 1.337(14) . ?
C28 H28 0.9300 . ?
C28 C29 1.363(17) . ?
C29 H29 0.9300 . ?
C29 C30 1.342(18) . ?
C30 H30 0.9300 . ?
C30 C31 1.405(17) . ?
C31 C32 1.413(15) . ?
C32 H32 0.9300 . ?
C32 C33 1.322(16) . ?
C33 H33 0.9300 . ?
C33 C34 1.425(14) . ?
C34 O1 1.435(13) . ?
C35 C36 1.368(16) . ?
C35 C40 1.367(15) . ?
C35 S1 1.739(12) . ?
C36 H36 0.9300 . ?
C36 C37 1.365(18) . ?
C37 H37 0.9300 . ?
C37 C38 1.358(16) . ?
C38 C39 1.378(18) . ?
C38 C41 1.498(18) . ?
C39 H39 0.9300 . ?
C39 C40 1.379(19) . ?
C40 H40 0.9300 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 C43 1.473(12) . ?
C42 N1 1.370(12) . ?
C42 O4 1.188(11) . ?
C43 C44 1.383(14) . ?
C43 C48 1.381(15) . ?
C44 H44 0.9300 . ?
C44 C45 1.415(17) . ?
C45 H45 0.9300 . ?
C45 C46 1.35(2) . ?
C46 H46 0.9300 . ?
C46 C47 1.29(2) . ?
C47 H47 0.9300 . ?
C47 C48 1.399(16) . ?
C48 H48 0.9300 . ?
N1 H1 0.81(10) . ?
N1 N2 1.394(9) . ?
O1 S1 1.607(8) . ?
O2 S1 1.421(9) . ?
O3 S1 1.424(9) . ?

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
C6 C1 C2 123.9(8) . . ?
N2 C1 C2 129.5(8) . . ?
N2 C1 C6 106.7(8) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 117.9(9) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.9(9) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C7 122.6(9) . . ?
C5 C4 C3 121.0(8) . . ?
C5 C4 C7 116.3(9) . . ?
C4 C5 C6 116.2(8) . . ?
C10 C5 C4 119.8(8) . . ?
C10 C5 C6 124.0(8) . . ?
C1 C6 C5 119.0(8) . . ?
C1 C6 C17 107.6(7) . . ?
C5 C6 C17 133.4(8) . . ?
C4 C7 H7 118.5 . . ?
C8 C7 C4 122.9(10) . . ?
C8 C7 H7 118.5 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.1(9) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C11 120.3(9) . . ?
C10 C9 C8 118.3(9) . . ?
C10 C9 C11 121.3(10) . . ?
C5 C10 H10 119.2 . . ?
C9 C10 C5 121.5(9) . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C9 123.3(14) . . ?
C16 C11 C9 119.9(10) . . ?
C16 C11 C12 116.7(12) . . ?
C11 C12 H12 117.7 . . ?
C13 C12 C11 124.6(16) . . ?
C13 C12 H12 117.7 . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.2(14) . . ?
C14 C13 H13 120.9 . . ?
C13 C14 H14 118.9 . . ?
C13 C14 C15 122.1(13) . . ?
C15 C14 H14 118.9 . . ?
C14 C15 H15 122.2 . . ?
C16 C15 C14 115.6(17) . . ?
C16 C15 H15 122.2 . . ?
C11 C16 C15 122.8(13) . . ?
C11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C6 C17 C18 127.4(7) . . ?
C24 C17 C6 106.8(7) . . ?
C24 C17 C18 125.8(8) . . ?
C19 C18 C17 120.6(8) . . ?
C19 C18 C23 116.2(8) . . ?
C23 C18 C17 123.0(8) . . ?
C18 C19 H19 118.5 . . ?
C18 C19 C20 123.0(9) . . ?
C20 C19 H19 118.5 . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.0(12) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.5(11) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.1(10) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 Br1 119.0(7) . . ?
C18 C23 C22 121.1(9) . . ?
C22 C23 Br1 119.9(8) . . ?
C17 C24 C25 131.8(8) . . ?
C17 C24 N2 108.0(7) . . ?
N2 C24 C25 120.2(7) . . ?
C26 C25 C24 120.0(7) . . ?
C34 C25 C24 122.9(9) . . ?
C34 C25 C26 117.0(8) . . ?
C27 C26 C25 122.2(8) . . ?
C31 C26 C25 120.5(8) . . ?
C31 C26 C27 117.1(9) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.8(10) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.6(12) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 119.1 . . ?
C30 C29 C28 121.9(12) . . ?
C30 C29 H29 119.1 . . ?
C29 C30 H30 119.9 . . ?
C29 C30 C31 120.2(12) . . ?
C31 C30 H30 119.9 . . ?
C26 C31 C32 117.5(10) . . ?
C30 C31 C26 119.2(10) . . ?
C30 C31 C32 123.1(11) . . ?
C31 C32 H32 118.7 . . ?
C33 C32 C31 122.6(10) . . ?
C33 C32 H32 118.7 . . ?
C32 C33 H33 120.9 . . ?
C32 C33 C34 118.2(10) . . ?
C34 C33 H33 120.9 . . ?
C25 C34 C33 124.0(10) . . ?
C25 C34 O1 118.3(8) . . ?
C33 C34 O1 117.6(9) . . ?
C36 C35 S1 120.7(9) . . ?
C40 C35 C36 120.8(11) . . ?
C40 C35 S1 118.2(9) . . ?
C35 C36 H36 120.6 . . ?
C37 C36 C35 118.7(10) . . ?
C37 C36 H36 120.6 . . ?
C36 C37 H37 118.4 . . ?
C38 C37 C36 123.2(11) . . ?
C38 C37 H37 118.4 . . ?
C37 C38 C39 116.5(12) . . ?
C37 C38 C41 124.8(13) . . ?
C39 C38 C41 118.7(12) . . ?
C38 C39 H39 118.8 . . ?
C38 C39 C40 122.5(11) . . ?
C40 C39 H39 118.8 . . ?
C35 C40 C39 118.2(12) . . ?
C35 C40 H40 120.9 . . ?
C39 C40 H40 120.9 . . ?
C38 C41 H41A 109.5 . . ?
C38 C41 H41B 109.5 . . ?
C38 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N1 C42 C43 113.4(8) . . ?
O4 C42 C43 123.4(9) . . ?
O4 C42 N1 123.1(8) . . ?
C44 C43 C42 118.3(9) . . ?
C48 C43 C42 123.1(9) . . ?
C48 C43 C44 118.6(9) . . ?
C43 C44 H44 120.3 . . ?
C43 C44 C45 119.5(12) . . ?
C45 C44 H44 120.3 . . ?
C44 C45 H45 120.2 . . ?
C46 C45 C44 119.6(13) . . ?
C46 C45 H45 120.2 . . ?
C45 C46 H46 119.4 . . ?
C47 C46 C45 121.1(12) . . ?
C47 C46 H46 119.4 . . ?
C46 C47 H47 118.7 . . ?
C46 C47 C48 122.5(13) . . ?
C48 C47 H47 118.7 . . ?
C43 C48 C47 118.7(12) . . ?
C43 C48 H48 120.7 . . ?
C47 C48 H48 120.7 . . ?
C42 N1 H1 120(7) . . ?
C42 N1 N2 121.2(8) . . ?
N2 N1 H1 118(7) . . ?
C1 N2 C24 110.9(6) . . ?
C1 N2 N1 124.9(8) . . ?
C24 N2 N1 124.0(7) . . ?
C34 O1 S1 113.6(6) . . ?
O1 S1 C35 100.8(4) . . ?
O2 S1 C35 110.8(6) . . ?
O2 S1 O1 107.0(5) . . ?
O2 S1 O3 117.4(6) . . ?
O3 S1 C35 110.1(5) . . ?
O3 S1 O1 109.4(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.81(10) 2.21(10) 2.899(12) 142(9) .

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
C1 C2 C3 C4 0.0(15) . . . . ?
C1 C6 C17 C18 178.5(8) . . . . ?
C1 C6 C17 C24 -0.6(10) . . . . ?
C2 C1 C6 C5 -2.5(14) . . . . ?
C2 C1 C6 C17 179.7(8) . . . . ?
C2 C1 N2 C24 -178.6(9) . . . . ?
C2 C1 N2 N1 -3.2(15) . . . . ?
C2 C3 C4 C5 1.8(15) . . . . ?
C2 C3 C4 C7 178.4(10) . . . . ?
C3 C4 C5 C6 -3.7(13) . . . . ?
C3 C4 C5 C10 175.7(9) . . . . ?
C3 C4 C7 C8 -175.2(10) . . . . ?
C4 C5 C6 C1 4.0(12) . . . . ?
C4 C5 C6 C17 -178.8(9) . . . . ?
C4 C5 C10 C9 -0.2(14) . . . . ?
C4 C7 C8 C9 -0.7(17) . . . . ?
C5 C4 C7 C8 1.6(15) . . . . ?
C5 C6 C17 C18 1.0(16) . . . . ?
C5 C6 C17 C24 -178.0(9) . . . . ?
C6 C1 C2 C3 0.4(14) . . . . ?
C6 C1 N2 C24 1.8(10) . . . . ?
C6 C1 N2 N1 177.2(8) . . . . ?
C6 C5 C10 C9 179.2(8) . . . . ?
C6 C17 C18 C19 -104.1(11) . . . . ?
C6 C17 C18 C23 71.6(12) . . . . ?
C6 C17 C24 C25 -177.0(9) . . . . ?
C6 C17 C24 N2 1.6(9) . . . . ?
C7 C4 C5 C6 179.4(8) . . . . ?
C7 C4 C5 C10 -1.2(12) . . . . ?
C7 C8 C9 C10 -0.7(15) . . . . ?
C7 C8 C9 C11 175.4(10) . . . . ?
C8 C9 C10 C5 1.1(14) . . . . ?
C8 C9 C11 C12 36.9(13) . . . . ?
C8 C9 C11 C16 -139.4(10) . . . . ?
C9 C11 C12 C13 -176.0(11) . . . . ?
C9 C11 C16 C15 176.1(9) . . . . ?
C10 C5 C6 C1 -175.4(8) . . . . ?
C10 C5 C6 C17 1.8(15) . . . . ?
C10 C9 C11 C12 -147.1(10) . . . . ?
C10 C9 C11 C16 36.5(13) . . . . ?
C11 C9 C10 C5 -174.9(9) . . . . ?
C11 C12 C13 C14 0(2) . . . . ?
C12 C11 C16 C15 -0.4(16) . . . . ?
C12 C13 C14 C15 -1(2) . . . . ?
C13 C14 C15 C16 1(2) . . . . ?
C14 C15 C16 C11 -0.3(17) . . . . ?
C16 C11 C12 C13 0.5(16) . . . . ?
C17 C18 C19 C20 174.9(9) . . . . ?
C17 C18 C23 Br1 5.1(11) . . . . ?
C17 C18 C23 C22 -174.6(8) . . . . ?
C17 C24 C25 C26 -108.7(11) . . . . ?
C17 C24 C25 C34 75.4(14) . . . . ?
C17 C24 N2 C1 -2.2(10) . . . . ?
C17 C24 N2 N1 -177.6(8) . . . . ?
C18 C17 C24 C25 4.0(15) . . . . ?
C18 C17 C24 N2 -177.4(8) . . . . ?
C18 C19 C20 C21 0.0(16) . . . . ?
C19 C18 C23 Br1 -179.0(6) . . . . ?
C19 C18 C23 C22 1.3(13) . . . . ?
C19 C20 C21 C22 0.9(18) . . . . ?
C20 C21 C22 C23 -0.7(18) . . . . ?
C21 C22 C23 Br1 179.9(8) . . . . ?
C21 C22 C23 C18 -0.5(15) . . . . ?
C23 C18 C19 C20 -1.0(14) . . . . ?
C24 C17 C18 C19 74.8(11) . . . . ?
C24 C17 C18 C23 -109.5(10) . . . . ?
C24 C25 C26 C27 0.4(13) . . . . ?
C24 C25 C26 C31 -175.7(9) . . . . ?
C24 C25 C34 C33 179.4(10) . . . . ?
C24 C25 C34 O1 3.2(14) . . . . ?
C25 C24 N2 C1 176.6(8) . . . . ?
C25 C24 N2 N1 1.2(13) . . . . ?
C25 C26 C27 C28 -171.0(10) . . . . ?
C25 C26 C31 C30 172.1(10) . . . . ?
C25 C26 C31 C32 -3.7(15) . . . . ?
C25 C34 O1 S1 104.3(9) . . . . ?
C26 C25 C34 C33 3.3(15) . . . . ?
C26 C25 C34 O1 -172.9(8) . . . . ?
C26 C27 C28 C29 -3.3(16) . . . . ?
C26 C31 C32 C33 3.3(18) . . . . ?
C27 C26 C31 C30 -4.2(15) . . . . ?
C27 C26 C31 C32 180.0(10) . . . . ?
C27 C28 C29 C30 0.3(18) . . . . ?
C28 C29 C30 C31 0.7(19) . . . . ?
C29 C30 C31 C26 1.4(18) . . . . ?
C29 C30 C31 C32 177.0(12) . . . . ?
C30 C31 C32 C33 -172.3(12) . . . . ?
C31 C26 C27 C28 5.2(14) . . . . ?
C31 C32 C33 C34 0.2(18) . . . . ?
C32 C33 C34 C25 -3.8(17) . . . . ?
C32 C33 C34 O1 172.4(10) . . . . ?
C33 C34 O1 S1 -72.2(10) . . . . ?
C34 C25 C26 C27 176.6(9) . . . . ?
C34 C25 C26 C31 0.5(13) . . . . ?
C34 O1 S1 C35 -171.7(6) . . . . ?
C34 O1 S1 O2 -55.8(8) . . . . ?
C34 O1 S1 O3 72.3(7) . . . . ?
C35 C36 C37 C38 -0.1(19) . . . . ?
C36 C35 C40 C39 4(2) . . . . ?
C36 C35 S1 O1 84.9(10) . . . . ?
C36 C35 S1 O2 -28.2(12) . . . . ?
C36 C35 S1 O3 -159.7(10) . . . . ?
C36 C37 C38 C39 2.6(19) . . . . ?
C36 C37 C38 C41 -176.5(12) . . . . ?
C37 C38 C39 C40 -2(2) . . . . ?
C38 C39 C40 C35 -1(2) . . . . ?
C40 C35 C36 C37 -3.3(19) . . . . ?
C40 C35 S1 O1 -102.0(11) . . . . ?
C40 C35 S1 O2 145.0(11) . . . . ?
C40 C35 S1 O3 13.5(13) . . . . ?
C41 C38 C39 C40 177.3(14) . . . . ?
C42 C43 C44 C45 -176.5(14) . . . . ?
C42 C43 C48 C47 177.1(14) . . . . ?
C42 N1 N2 C1 79.4(13) . . . . ?
C42 N1 N2 C24 -105.8(10) . . . . ?
C43 C42 N1 N2 170.5(9) . . . . ?
C43 C44 C45 C46 -2(3) . . . . ?
C44 C43 C48 C47 -2(2) . . . . ?
C44 C45 C46 C47 2(4) . . . . ?
C45 C46 C47 C48 -1(4) . . . . ?
C46 C47 C48 C43 1(3) . . . . ?
C48 C43 C44 C45 2(2) . . . . ?
N1 C42 C43 C44 152.5(11) . . . . ?
N1 C42 C43 C48 -26.2(17) . . . . ?
N2 C1 C2 C3 -179.2(10) . . . . ?
N2 C1 C6 C5 177.2(7) . . . . ?
N2 C1 C6 C17 -0.7(10) . . . . ?
N2 C24 C25 C26 72.9(11) . . . . ?
N2 C24 C25 C34 -103.1(11) . . . . ?
O4 C42 C43 C44 -24.1(17) . . . . ?
O4 C42 C43 C48 157.2(12) . . . . ?
O4 C42 N1 N2 -13.0(16) . . . . ?
S1 C35 C36 C37 169.7(9) . . . . ?
S1 C35 C40 C39 -169.2(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# SQUEEZE RESULTS (Version = 150216)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.037 0.000 466 127 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
####################################################################### 
# 
# 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_xb1847_0m
_database_code_depnum_ccdc_archive 'CCDC 1905908'
loop_
_audit_author_name
_audit_author_address
'yulong hu'
;northwest university
China
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H25 Br1 N2 O2'
_chemical_formula_weight         585.47

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.5449(16)
_cell_length_b                   11.993(2)
_cell_length_c                   13.598(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.922(3)
_cell_angle_gamma                90.00
_cell_volume                     1346.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2358
_cell_measurement_theta_min      2.305
_cell_measurement_theta_max      22.923

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      1.444
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    1.562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8407
_exptl_absorpt_correction_T_max  0.8918
_exptl_absorpt_process_details   sadaba

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7098
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.99
_reflns_number_total             5307
_reflns_number_gt                3785
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0000P)²+0.0068P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constra
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(8)
_refine_ls_number_reflns         4936
_refine_ls_number_parameters     362
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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 0.16738(5) 0.05798(4) 0.85937(3) 0.06228(14) Uani 1 1 d . . .
O1 O 0.3913(3) 0.5580(3) 0.70825(17) 0.0579(6) Uani 1 1 d . . .
O2 O 0.4869(4) 0.1245(2) 0.6373(2) 0.0650(8) Uani 1 1 d . . .
H2 H 0.4356 0.1802 0.6129 0.098 Uiso 1 1 calc R . .
C26 C 0.6884(4) 0.0515(5) 0.8979(3) 0.0631(10) Uani 1 1 d . . .
H26 H 0.7529 -0.0060 0.9321 0.076 Uiso 1 1 calc R . .
C27 C 0.6398(5) 0.0511(5) 0.7936(3) 0.0641(11) Uani 1 1 d . . .
H27 H 0.6748 -0.0052 0.7573 0.077 Uiso 1 1 calc R . .
N1 N 0.5220(4) 0.4197(2) 0.6494(2) 0.0448(7) Uani 1 1 d . . .
H1B H 0.5436 0.4262 0.5883 0.054 Uiso 1 1 d R . .
N2 N 0.3945(4) 0.3433(2) 0.6374(2) 0.0427(7) Uani 1 1 d . . .
C13 C 0.0973(4) 0.2826(3) 0.7843(2) 0.0365(8) Uani 1 1 d . . .
C2 C 0.2155(6) 0.4416(3) 0.4847(3) 0.0513(10) Uani 1 1 d . . .
H2A H 0.3011 0.4765 0.4665 0.062 Uiso 1 1 calc R . .
C29 C 0.5093(5) 0.5261(3) 0.6836(3) 0.0434(9) Uani 1 1 d . . .
C18 C 0.0842(4) 0.2056(3) 0.8581(3) 0.0407(8) Uani 1 1 d . . .
C10 C -0.1725(5) 0.2661(3) 0.5568(3) 0.0452(9) Uani 1 1 d . . .
H10 H -0.1583 0.2225 0.6150 0.054 Uiso 1 1 calc R . .
C12 C 0.1859(4) 0.2605(3) 0.7018(2) 0.0385(8) Uani 1 1 d . . .
H12 H 0.1871 0.1803 0.6884 0.046 Uiso 1 1 calc R . .
C6 C 0.1191(4) 0.3226(3) 0.6027(2) 0.0388(8) Uani 1 1 d . . .
C25 C 0.6412(5) 0.1385(3) 0.9534(3) 0.0531(10) Uani 1 1 d . . .
C7 C -0.2281(6) 0.4026(3) 0.3852(3) 0.0551(11) Uani 1 1 d . . .
H7 H -0.2486 0.4498 0.3290 0.066 Uiso 1 1 calc R . .
C19 C 0.4864(4) 0.2212(3) 0.7924(3) 0.0424(8) Uani 1 1 d . . .
C3 C 0.0626(5) 0.4534(3) 0.4280(3) 0.0530(11) Uani 1 1 d . . .
H3 H 0.0424 0.5003 0.3717 0.064 Uiso 1 1 calc R . .
C5 C -0.0411(5) 0.3281(3) 0.5398(3) 0.0425(9) Uani 1 1 d . . .
C24 C 0.6939(5) 0.1399(4) 1.0587(4) 0.0664(12) Uani 1 1 d . . .
H24 H 0.7588 0.0823 1.0926 0.080 Uiso 1 1 calc R . .
C17 C 0.0105(5) 0.2313(3) 0.9342(3) 0.0520(10) Uani 1 1 d . . .
H17 H 0.0038 0.1781 0.9827 0.062 Uiso 1 1 calc R . .
C1 C 0.2422(5) 0.3743(3) 0.5728(3) 0.0428(9) Uani 1 1 d . . .
C15 C -0.0405(5) 0.4143(4) 0.8677(3) 0.0555(10) Uani 1 1 d . . .
H15 H -0.0833 0.4852 0.8704 0.067 Uiso 1 1 calc R . .
C4 C -0.0690(5) 0.3971(3) 0.4511(3) 0.0447(9) Uani 1 1 d . . .
C21 C 0.5035(5) 0.3132(4) 0.9613(3) 0.0533(11) Uani 1 1 d . . .
H21 H 0.4388 0.3720 0.9298 0.064 Uiso 1 1 calc R . .
C20 C 0.5414(4) 0.2260(3) 0.9006(3) 0.0452(9) Uani 1 1 d . . .
C9 C -0.3193(5) 0.2700(3) 0.4883(3) 0.0540(10) Uani 1 1 d . . .
H9 H -0.4021 0.2247 0.4985 0.065 Uiso 1 1 calc R . .
C30 C 0.6564(5) 0.5951(3) 0.6898(3) 0.0483(9) Uani 1 1 d . . .
C22 C 0.5594(5) 0.3127(4) 1.0636(3) 0.0639(13) Uani 1 1 d . . .
H22 H 0.5357 0.3720 1.1014 0.077 Uiso 1 1 calc R . .
C28 C 0.5376(5) 0.1352(3) 0.7414(3) 0.0494(10) Uani 1 1 d . . .
C31 C 0.6974(6) 0.6732(3) 0.7685(3) 0.0618(11) Uani 1 1 d . . .
H31 H 0.6316 0.6815 0.8129 0.074 Uiso 1 1 calc R . .
C11 C 0.3622(4) 0.3049(3) 0.7358(3) 0.0384(8) Uani 1 1 d . . .
H11 H 0.3642 0.3700 0.7797 0.046 Uiso 1 1 calc R . .
C8 C -0.3508(5) 0.3396(4) 0.4032(3) 0.0578(11) Uani 1 1 d . . .
H8 H -0.4540 0.3430 0.3593 0.069 Uiso 1 1 calc R . .
C34 C 0.8945(6) 0.6504(5) 0.6382(4) 0.0837(17) Uani 1 1 d . . .
H34 H 0.9613 0.6441 0.5941 0.100 Uiso 1 1 calc R . .
C32 C 0.8325(7) 0.7373(4) 0.7810(4) 0.0784(15) Uani 1 1 d . . .
H32 H 0.8566 0.7900 0.8329 0.094 Uiso 1 1 calc R . .
C33 C 0.9323(7) 0.7253(4) 0.7189(5) 0.092(2) Uani 1 1 d . . .
H33 H 1.0267 0.7674 0.7303 0.111 Uiso 1 1 calc R . .
C23 C 0.6515(6) 0.2244(5) 1.1126(3) 0.0735(14) Uani 1 1 d . . .
H23 H 0.6848 0.2232 1.1833 0.088 Uiso 1 1 calc R . .
C35 C 0.7536(5) 0.5838(3) 0.6235(3) 0.0599(12) Uani 1 1 d . . .
H35 H 0.7268 0.5332 0.5700 0.072 Uiso 1 1 calc R . .
C14 C 0.0353(5) 0.3884(3) 0.7928(3) 0.0503(9) Uani 1 1 d . . .
H14 H 0.0454 0.4433 0.7465 0.060 Uiso 1 1 calc R . .
C16 C -0.0530(5) 0.3360(4) 0.9380(3) 0.0597(11) Uani 1 1 d . . .
H16 H -0.1044 0.3534 0.9886 0.072 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 C18 1.906(3) . ?
O1 C29 1.204(4) . ?
O2 C28 1.376(5) . ?
O2 H2 0.8200 . ?
C26 C27 1.371(5) . ?
C26 C25 1.406(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.401(6) . ?
C27 H27 0.9300 . ?
N1 C29 1.372(4) . ?
N1 N2 1.401(4) . ?
N1 H1B 0.9000 . ?
N2 C1 1.419(5) . ?
N2 C11 1.507(4) . ?
C13 C18 1.390(4) . ?
C13 C14 1.391(5) . ?
C13 C12 1.529(4) . ?
C2 C3 1.343(6) . ?
C2 C1 1.414(5) . ?
C2 H2A 0.9300 . ?
C29 C30 1.489(5) . ?
C18 C17 1.377(5) . ?
C10 C9 1.357(5) . ?
C10 C5 1.415(5) . ?
C10 H10 0.9300 . ?
C12 C6 1.517(5) . ?
C12 C11 1.551(5) . ?
C12 H12 0.9800 . ?
C6 C1 1.370(5) . ?
C6 C5 1.416(5) . ?
C25 C24 1.385(6) . ?
C25 C20 1.425(5) . ?
C7 C8 1.364(6) . ?
C7 C4 1.424(6) . ?
C7 H7 0.9300 . ?
C19 C28 1.375(5) . ?
C19 C20 1.426(5) . ?
C19 C11 1.518(5) . ?
C3 C4 1.414(5) . ?
C3 H3 0.9300 . ?
C5 C4 1.431(4) . ?
C24 C23 1.354(6) . ?
C24 H24 0.9300 . ?
C17 C16 1.374(6) . ?
C17 H17 0.9300 . ?
C15 C16 1.364(6) . ?
C15 C14 1.376(5) . ?
C15 H15 0.9300 . ?
C21 C22 1.349(5) . ?
C21 C20 1.419(6) . ?
C21 H21 0.9300 . ?
C9 C8 1.396(6) . ?
C9 H9 0.9300 . ?
C30 C35 1.381(5) . ?
C30 C31 1.397(5) . ?
C22 C23 1.383(7) . ?
C22 H22 0.9300 . ?
C31 C32 1.360(6) . ?
C31 H31 0.9300 . ?
C11 H11 0.9800 . ?
C8 H8 0.9300 . ?
C34 C33 1.391(8) . ?
C34 C35 1.415(6) . ?
C34 H34 0.9300 . ?
C32 C33 1.353(8) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C23 H23 0.9300 . ?
C35 H35 0.9300 . ?
C14 H14 0.9300 . ?
C16 H16 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
C28 O2 H2 109.5 . . ?
C27 C26 C25 120.4(4) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 120.3(4) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C29 N1 N2 121.4(3) . . ?
C29 N1 H1B 106.6 . . ?
N2 N1 H1B 106.7 . . ?
N1 N2 C1 117.5(3) . . ?
N1 N2 C11 114.3(3) . . ?
C1 N2 C11 106.4(3) . . ?
C18 C13 C14 116.3(3) . . ?
C18 C13 C12 124.2(3) . . ?
C14 C13 C12 119.3(3) . . ?
C3 C2 C1 117.8(4) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
O1 C29 N1 122.3(3) . . ?
O1 C29 C30 124.3(3) . . ?
N1 C29 C30 113.4(3) . . ?
C17 C18 C13 122.1(3) . . ?
C17 C18 Br1 116.3(3) . . ?
C13 C18 Br1 121.6(3) . . ?
C9 C10 C5 120.1(4) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?
C6 C12 C13 115.0(3) . . ?
C6 C12 C11 102.2(3) . . ?
C13 C12 C11 110.4(3) . . ?
C6 C12 H12 109.7 . . ?
C13 C12 H12 109.7 . . ?
C11 C12 H12 109.7 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 C12 110.1(3) . . ?
C5 C6 C12 130.1(3) . . ?
C24 C25 C26 120.1(4) . . ?
C24 C25 C20 120.3(4) . . ?
C26 C25 C20 119.5(4) . . ?
C8 C7 C4 121.0(4) . . ?
C8 C7 H7 119.5 . . ?
C4 C7 H7 119.5 . . ?
C28 C19 C20 119.2(3) . . ?
C28 C19 C11 120.8(3) . . ?
C20 C19 C11 119.8(3) . . ?
C2 C3 C4 122.3(3) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C10 C5 C6 124.1(3) . . ?
C10 C5 C4 118.3(3) . . ?
C6 C5 C4 117.5(3) . . ?
C23 C24 C25 120.5(4) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C16 C17 C18 119.6(4) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C6 C1 C2 122.7(4) . . ?
C6 C1 N2 110.5(3) . . ?
C2 C1 N2 126.6(3) . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C3 C4 C7 121.5(3) . . ?
C3 C4 C5 119.6(3) . . ?
C7 C4 C5 118.8(4) . . ?
C22 C21 C20 121.6(4) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C20 C25 116.5(3) . . ?
C21 C20 C19 124.5(3) . . ?
C25 C20 C19 119.0(3) . . ?
C10 C9 C8 122.5(4) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C35 C30 C31 119.4(4) . . ?
C35 C30 C29 123.3(4) . . ?
C31 C30 C29 117.2(4) . . ?
C21 C22 C23 120.4(4) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C19 C28 O2 122.1(3) . . ?
C19 C28 C27 121.5(4) . . ?
O2 C28 C27 116.4(3) . . ?
C32 C31 C30 120.8(5) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
N2 C11 C19 112.8(3) . . ?
N2 C11 C12 103.0(3) . . ?
C19 C11 C12 115.0(3) . . ?
N2 C11 H11 108.6 . . ?
C19 C11 H11 108.6 . . ?
C12 C11 H11 108.6 . . ?
C7 C8 C9 119.1(4) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C33 C34 C35 119.4(5) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C33 C32 C31 120.9(5) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C34 120.4(5) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C30 C35 C34 119.0(4) . . ?
C30 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
C15 C14 C13 121.9(4) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1884267'
loop_
_audit_author_name
_audit_author_address
'yulong hu'
;northwest university
China
;
_audit_update_record             
;
2019-03-26 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H25 Br N2 O2'
_chemical_formula_weight         585.48

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_cell_length_a                   15.0667(4)
_cell_length_b                   15.0667(4)
_cell_length_c                   22.0098(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4327.0(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9780
_cell_measurement_theta_min      2.421
_cell_measurement_theta_max      22.927

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             1800
_exptl_transmission_factor_min   0.6329
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.459
_shelx_estimated_absorpt_T_min   0.749
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            116363
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.1357
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.814
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5058
_reflns_number_gt                4244
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_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 SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0139P)²+5.2688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 1793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5058
_refine_ls_number_parameters     362
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.33882(7) 0.03796(7) 0.74624(4) 0.0823(3) Uani 1 1 d . . . . .
C1 C 0.3248(4) 0.3650(4) 0.4392(2) 0.0401(13) Uani 1 1 d . . . . .
H1 H 0.2744 0.3828 0.4542 0.048 Uiso 1 1 calc R U . . .
C2 C 0.3851(4) 0.4376(5) 0.3886(2) 0.0427(13) Uani 1 1 d . . . . .
C3 C 0.4402(5) 0.4151(5) 0.3479(3) 0.0552(16) Uani 1 1 d . . . . .
C4 C 0.4957(6) 0.4826(7) 0.2996(3) 0.071(2) Uani 1 1 d . . . . .
H4 H 0.5299 0.4647 0.2713 0.085 Uiso 1 1 calc R U . . .
C5 C 0.4983(6) 0.5738(7) 0.2951(3) 0.072(2) Uani 1 1 d . . . . .
H5 H 0.5355 0.6184 0.2638 0.086 Uiso 1 1 calc R U . . .
C6 C 0.4468(5) 0.6023(5) 0.3361(3) 0.0585(17) Uani 1 1 d . . . . .
C7 C 0.3888(5) 0.5346(5) 0.3833(3) 0.0463(15) Uani 1 1 d . . . . .
C8 C 0.3382(5) 0.5662(5) 0.4249(3) 0.0580(17) Uani 1 1 d . . . . .
H8 H 0.2990 0.5223 0.4561 0.070 Uiso 1 1 calc R U . . .
C9 C 0.3462(6) 0.6611(6) 0.4198(4) 0.071(2) Uani 1 1 d . . . . .
H9 H 0.3131 0.6810 0.4477 0.086 Uiso 1 1 calc R U . . .
C10 C 0.4033(7) 0.7265(6) 0.3736(4) 0.077(2) Uani 1 1 d . . . . .
H10 H 0.4087 0.7906 0.3707 0.093 Uiso 1 1 calc R U . . .
C11 C 0.4512(6) 0.6989(6) 0.3327(4) 0.076(2) Uani 1 1 d . . . . .
H11 H 0.4882 0.7439 0.3014 0.091 Uiso 1 1 calc R U . . .
C12 C 0.3886(4) 0.3621(4) 0.4938(2) 0.0390(12) Uani 1 1 d . . . . .
H12 H 0.4544 0.3727 0.4788 0.047 Uiso 1 1 calc R U . . .
C13 C 0.3230(4) 0.2507(4) 0.5148(3) 0.0391(12) Uani 1 1 d . . . . .
C14 C 0.2541(5) 0.1952(4) 0.4704(3) 0.0416(13) Uani 1 1 d . . . . .
C15 C 0.1845(5) 0.0887(5) 0.4769(3) 0.0495(15) Uani 1 1 d . . . . .
H15 H 0.1375 0.0517 0.4465 0.059 Uiso 1 1 calc R U . . .
C16 C 0.1888(5) 0.0422(5) 0.5291(3) 0.0515(15) Uani 1 1 d . . . . .
H16 H 0.1427 -0.0273 0.5342 0.062 Uiso 1 1 calc R U . . .
C17 C 0.2603(4) 0.0952(4) 0.5757(3) 0.0444(13) Uani 1 1 d . . . . .
C18 C 0.3310(4) 0.2035(4) 0.5678(3) 0.0408(13) Uani 1 1 d . . . . .
C19 C 0.4041(5) 0.2546(5) 0.6142(3) 0.0482(15) Uani 1 1 d . . . . .
H19 H 0.4511 0.3241 0.6097 0.058 Uiso 1 1 calc R U . . .
C20 C 0.4079(5) 0.2056(5) 0.6652(3) 0.0553(16) Uani 1 1 d . . . . .
H20 H 0.4575 0.2410 0.6947 0.066 Uiso 1 1 calc R U . . .
C21 C 0.3355(5) 0.1000(5) 0.6730(3) 0.0517(15) Uani 1 1 d . . . . .
C22 C 0.2649(5) 0.0469(5) 0.6295(3) 0.0507(15) Uani 1 1 d . . . . .
H22 H 0.2188 -0.0225 0.6351 0.061 Uiso 1 1 calc R U . . .
C23 C 0.4082(4) 0.4447(4) 0.5393(2) 0.0393(13) Uani 1 1 d . . . . .
C24 C 0.5002(5) 0.5372(5) 0.5386(3) 0.0564(17) Uani 1 1 d . . . . .
H24 H 0.5515 0.5468 0.5114 0.068 Uiso 1 1 calc R U . . .
C25 C 0.5162(6) 0.6152(5) 0.5783(4) 0.075(2) Uani 1 1 d . . . . .
H25 H 0.5781 0.6767 0.5773 0.089 Uiso 1 1 calc R U . . .
C26 C 0.4427(7) 0.6034(6) 0.6187(4) 0.080(2) Uani 1 1 d . . . . .
H26 H 0.4539 0.6564 0.6450 0.096 Uiso 1 1 calc R U . . .
C27 C 0.3505(6) 0.5109(6) 0.6201(4) 0.077(2) Uani 1 1 d . . . . .
H27 H 0.2998 0.5014 0.6478 0.093 Uiso 1 1 calc R U . . .
C28 C 0.3344(5) 0.4334(5) 0.5806(3) 0.0558(16) Uani 1 1 d . . . . .
H28 H 0.2724 0.3721 0.5819 0.067 Uiso 1 1 calc R U . . .
C29 C 0.1022(5) 0.2347(5) 0.3986(3) 0.0460(14) Uani 1 1 d . . . . .
C30 C 0.0267(5) 0.2204(5) 0.3496(3) 0.0550(16) Uani 1 1 d . . . . .
C31 C 0.0215(6) 0.1761(7) 0.2952(4) 0.084(3) Uani 1 1 d . . . . .
H31 H 0.0646 0.1498 0.2874 0.100 Uiso 1 1 calc R U . . .
C32 C -0.0474(8) 0.1694(9) 0.2508(5) 0.113(4) Uani 1 1 d . . . . .
H32 H -0.0499 0.1400 0.2132 0.136 Uiso 1 1 calc R U . . .
C33 C -0.1109(8) 0.2068(8) 0.2637(6) 0.112(4) Uani 1 1 d . . . . .
H33 H -0.1575 0.2025 0.2346 0.135 Uiso 1 1 calc R U . . .
C34 C -0.1074(7) 0.2491(8) 0.3171(6) 0.100(3) Uani 1 1 d . . . . .
H34 H -0.1522 0.2734 0.3248 0.120 Uiso 1 1 calc R U . . .
C35 C -0.0391(6) 0.2580(7) 0.3616(4) 0.081(2) Uani 1 1 d . . . . .
H35 H -0.0370 0.2884 0.3987 0.097 Uiso 1 1 calc R U . . .
N1 N 0.1856(4) 0.2304(4) 0.3798(2) 0.0446(12) Uani 1 1 d . . . . .
H1B H 0.1876 0.2122 0.3430 0.054 Uiso 1 1 calc R U . . .
N2 N 0.2688(4) 0.2548(3) 0.4184(2) 0.0420(11) Uani 1 1 d . . . . .
O1 O 0.4452(4) 0.3266(4) 0.3508(3) 0.0718(14) Uani 1 1 d . . . . .
H1A H 0.3945 0.2821 0.3684 0.108 Uiso 1 1 calc R U . . .
O2 O 0.0911(3) 0.2505(4) 0.45168(19) 0.0590(12) 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 C21 1.876(6) . ?
C1 C2 1.506(8) . ?
C1 N2 1.509(7) . ?
C1 C12 1.554(8) . ?
C1 H1 0.9800 . ?
C2 C3 1.375(8) . ?
C2 C7 1.439(9) . ?
C3 O1 1.375(8) . ?
C3 C4 1.419(10) . ?
C4 C5 1.359(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.411(9) . ?
C6 C11 1.425(11) . ?
C7 C8 1.419(9) . ?
C8 C9 1.377(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.344(12) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C23 1.506(8) . ?
C12 C13 1.533(7) . ?
C12 H12 0.9800 . ?
C13 C14 1.365(8) . ?
C13 C18 1.403(8) . ?
C14 N2 1.403(7) . ?
C14 C15 1.418(9) . ?
C15 C16 1.364(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.411(9) . ?
C16 H16 0.9300 . ?
C17 C22 1.409(9) . ?
C17 C18 1.445(8) . ?
C18 C19 1.415(8) . ?
C19 C20 1.360(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.419(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.357(9) . ?
C22 H22 0.9300 . ?
C23 C28 1.381(8) . ?
C23 C24 1.391(8) . ?
C24 C25 1.386(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.360(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.392(11) . ?
C26 H26 0.9300 . ?
C27 C28 1.376(9) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 O2 1.220(7) . ?
C29 N1 1.356(8) . ?
C29 C30 1.504(9) . ?
C30 C31 1.353(10) . ?
C30 C35 1.391(10) . ?
C31 C32 1.391(12) . ?
C31 H31 0.9300 . ?
C32 C33 1.362(15) . ?
C32 H32 0.9300 . ?
C33 C34 1.326(15) . ?
C33 H33 0.9300 . ?
C34 C35 1.377(12) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
N1 N2 1.403(6) . ?
N1 H1B 0.8600 . ?
O1 H1A 0.8200 . ?

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
C2 C1 N2 112.2(4) . . ?
C2 C1 C12 115.8(5) . . ?
N2 C1 C12 102.5(4) . . ?
C2 C1 H1 108.7 . . ?
N2 C1 H1 108.7 . . ?
C12 C1 H1 108.7 . . ?
C3 C2 C7 118.5(6) . . ?
C3 C2 C1 121.5(6) . . ?
C7 C2 C1 120.0(5) . . ?
C2 C3 O1 122.9(6) . . ?
C2 C3 C4 121.5(7) . . ?
O1 C3 C4 115.6(6) . . ?
C5 C4 C3 119.2(7) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.9(7) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C7 119.5(7) . . ?
C5 C6 C11 122.2(7) . . ?
C7 C6 C11 118.3(7) . . ?
C6 C7 C8 118.3(6) . . ?
C6 C7 C2 119.3(6) . . ?
C8 C7 C2 122.3(5) . . ?
C9 C8 C7 120.9(7) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.2(8) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.9(7) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C6 121.5(7) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C23 C12 C13 117.2(4) . . ?
C23 C12 C1 111.1(4) . . ?
C13 C12 C1 101.2(4) . . ?
C23 C12 H12 109.0 . . ?
C13 C12 H12 109.0 . . ?
C1 C12 H12 109.0 . . ?
C14 C13 C18 121.1(5) . . ?
C14 C13 C12 109.4(5) . . ?
C18 C13 C12 129.4(5) . . ?
C13 C14 N2 111.3(5) . . ?
C13 C14 C15 121.8(5) . . ?
N2 C14 C15 126.7(5) . . ?
C16 C15 C14 117.9(6) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C15 C16 C17 122.8(6) . . ?
C15 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C22 C17 C16 122.6(6) . . ?
C22 C17 C18 119.1(6) . . ?
C16 C17 C18 118.3(5) . . ?
C13 C18 C19 124.4(5) . . ?
C13 C18 C17 118.1(5) . . ?
C19 C18 C17 117.5(5) . . ?
C20 C19 C18 122.2(6) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C19 C20 C21 119.4(6) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 120.8(6) . . ?
C22 C21 Br1 121.4(5) . . ?
C20 C21 Br1 117.7(5) . . ?
C21 C22 C17 121.0(6) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
C28 C23 C24 117.9(6) . . ?
C28 C23 C12 121.6(5) . . ?
C24 C23 C12 120.5(5) . . ?
C25 C24 C23 120.5(6) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 121.1(7) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 119.0(7) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
C28 C27 C26 120.0(7) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C23 121.5(6) . . ?
C27 C28 H28 119.2 . . ?
C23 C28 H28 119.2 . . ?
O2 C29 N1 121.5(6) . . ?
O2 C29 C30 123.2(6) . . ?
N1 C29 C30 115.3(5) . . ?
C31 C30 C35 119.4(7) . . ?
C31 C30 C29 124.0(6) . . ?
C35 C30 C29 116.6(7) . . ?
C30 C31 C32 121.0(9) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C33 C32 C31 118.4(10) . . ?
C33 C32 H32 120.8 . . ?
C31 C32 H32 120.8 . . ?
C34 C33 C32 121.2(10) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C33 C34 C35 121.6(10) . . ?
C33 C34 H34 119.2 . . ?
C35 C34 H34 119.2 . . ?
C34 C35 C30 118.4(9) . . ?
C34 C35 H35 120.8 . . ?
C30 C35 H35 120.8 . . ?
C29 N1 N2 122.1(5) . . ?
C29 N1 H1B 119.0 . . ?
N2 N1 H1B 119.0 . . ?
C14 N2 N1 119.4(5) . . ?
C14 N2 C1 106.3(4) . . ?
N1 N2 C1 114.0(4) . . ?
C3 O1 H1A 109.5 . . ?

_refine_diff_density_max         0.642
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.054

