# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_z
_audit_block_doi                 10.5517/ccdc.csd.cc1pt9qj
_database_code_depnum_ccdc_archive 'CCDC 1573458'
_audit_update_record             
;
2017-09-08 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Br N O2'
_chemical_formula_weight         434.32

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   6.6297(15)
_cell_length_b                   15.443(4)
_cell_length_c                   20.287(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2077.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3036
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      20.21

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    1.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5690
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10202
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3639
_reflns_number_gt                2689
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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+0.0576P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_chemical_absolute_configuration rm
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(8)
_refine_ls_number_reflns         3639
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0653
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_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 1.02232(5) -0.01096(2) 0.970669(15) 0.09616(17) Uani 1 1 d . . .
O2 O 0.0117(3) 0.33007(11) 0.94479(8) 0.0710(5) Uani 1 1 d . . .
C6 C 0.5570(4) 0.01081(14) 0.80007(11) 0.0550(6) Uani 1 1 d . . .
C3 C 0.8343(4) -0.00091(17) 0.90099(13) 0.0635(7) Uani 1 1 d . . .
N1 N 0.3459(4) 0.08231(12) 0.71664(10) 0.0564(6) Uani 1 1 d . . .
C5 C 0.5181(5) 0.04681(15) 0.86067(12) 0.0654(7) Uani 1 1 d . . .
H5 H 0.3968 0.0756 0.8677 0.078 Uiso 1 1 calc R . .
C13 C 0.2517(4) 0.16669(17) 0.62994(13) 0.0604(7) Uani 1 1 d . . .
C4 C 0.6557(5) 0.04085(17) 0.91098(13) 0.0676(8) Uani 1 1 d . . .
H4 H 0.6272 0.0653 0.9518 0.081 Uiso 1 1 calc R . .
C20 C 0.0053(4) 0.22588(15) 0.85536(12) 0.0622(7) Uani 1 1 d . . .
H20 H -0.1252 0.2082 0.8655 0.075 Uiso 1 1 calc R . .
C21 C 0.0955(4) 0.29005(16) 0.89119(12) 0.0532(6) Uani 1 1 d . . .
C22 C 0.2877(4) 0.31652(16) 0.87456(13) 0.0611(7) Uani 1 1 d . . .
H22 H 0.3489 0.3611 0.8980 0.073 Uiso 1 1 calc R . .
C18 C 0.3033(4) 0.21112(14) 0.78824(11) 0.0479(6) Uani 1 1 d . . .
C17 C 0.4221(4) 0.16930(13) 0.73356(11) 0.0531(6) Uani 1 1 d . . .
H17 H 0.5644 0.1655 0.7463 0.064 Uiso 1 1 calc R . .
O1 O 0.3376(4) -0.06288(12) 0.72813(11) 0.1026(8) Uani 1 1 d . . .
C2 C 0.8784(4) -0.03640(17) 0.84065(15) 0.0712(8) Uani 1 1 d . . .
H2 H 1.0012 -0.0641 0.8338 0.085 Uiso 1 1 calc R . .
C19 C 0.1086(4) 0.18735(17) 0.80399(13) 0.0632(7) Uani 1 1 d . . .
H19 H 0.0453 0.1444 0.7794 0.076 Uiso 1 1 calc R . .
C7 C 0.4047(4) 0.00705(17) 0.74606(13) 0.0637(7) Uani 1 1 d . . .
C23 C 0.3892(4) 0.27743(15) 0.82359(12) 0.0566(7) Uani 1 1 d . . .
H23 H 0.5183 0.2962 0.8128 0.068 Uiso 1 1 calc R . .
C1 C 0.7406(4) -0.03080(17) 0.79064(14) 0.0671(8) Uani 1 1 d . . .
H1 H 0.7701 -0.0551 0.7498 0.081 Uiso 1 1 calc R . .
C14 C 0.4028(4) 0.22008(16) 0.66745(12) 0.0612(7) Uani 1 1 d . . .
H14 H 0.3474 0.2779 0.6759 0.073 Uiso 1 1 calc R . .
C11 C 0.0199(6) 0.1249(2) 0.54614(15) 0.0889(9) Uani 1 1 d . . .
H11 H -0.0491 0.1368 0.5073 0.107 Uiso 1 1 calc R . .
C8 C 0.2239(4) 0.08731(17) 0.65960(12) 0.0595(7) Uani 1 1 d . . .
C10 C -0.0075(5) 0.0466(2) 0.57701(14) 0.0823(9) Uani 1 1 d . . .
H10 H -0.0970 0.0066 0.5592 0.099 Uiso 1 1 calc R . .
C9 C 0.0946(5) 0.02635(19) 0.63347(14) 0.0714(8) Uani 1 1 d . . .
H9 H 0.0774 -0.0272 0.6537 0.086 Uiso 1 1 calc R . .
C12 C 0.1489(5) 0.1859(2) 0.57241(14) 0.0792(9) Uani 1 1 d . . .
H12 H 0.1665 0.2392 0.5518 0.095 Uiso 1 1 calc R . .
C24 C -0.1836(5) 0.3059(3) 0.96325(17) 0.1072(12) Uani 1 1 d . . .
H24A H -0.1878 0.2446 0.9709 0.161 Uiso 1 1 calc R . .
H24B H -0.2762 0.3206 0.9286 0.161 Uiso 1 1 calc R . .
H24C H -0.2208 0.3360 1.0029 0.161 Uiso 1 1 calc R . .
C15 C 0.5987(5) 0.22774(19) 0.63206(13) 0.0702(8) Uani 1 1 d . . .
H15 H 0.6654 0.1767 0.6212 0.084 Uiso 1 1 calc R . .
C16 C 0.6828(6) 0.2995(2) 0.61532(16) 0.0996(12) Uani 1 1 d . . .
H16A H 0.6206 0.3519 0.6253 0.119 Uiso 1 1 calc R . .
H16B H 0.8057 0.2990 0.5932 0.119 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 C3 1.891(3) . ?
O2 C21 1.369(3) . ?
O2 C24 1.398(4) . ?
C6 C5 1.374(3) . ?
C6 C1 1.389(3) . ?
C6 C7 1.491(4) . ?
C3 C4 1.363(4) . ?
C3 C2 1.373(4) . ?
N1 C7 1.363(3) . ?
N1 C8 1.414(3) . ?
N1 C17 1.476(3) . ?
C5 C4 1.372(4) . ?
C5 H5 0.9300 . ?
C13 C8 1.378(3) . ?
C13 C12 1.384(4) . ?
C13 C14 1.504(4) . ?
C4 H4 0.9300 . ?
C20 C21 1.367(3) . ?
C20 C19 1.382(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(4) . ?
C22 C23 1.373(3) . ?
C22 H22 0.9300 . ?
C18 C23 1.374(3) . ?
C18 C19 1.379(4) . ?
C18 C17 1.506(3) . ?
C17 C14 1.559(3) . ?
C17 H17 0.9800 . ?
O1 C7 1.223(3) . ?
C2 C1 1.368(4) . ?
C2 H2 0.9300 . ?
C19 H19 0.9300 . ?
C23 H23 0.9300 . ?
C1 H1 0.9300 . ?
C14 C15 1.489(4) . ?
C14 H14 0.9800 . ?
C11 C10 1.374(4) . ?
C11 C12 1.380(4) . ?
C11 H11 0.9300 . ?
C8 C9 1.379(4) . ?
C10 C9 1.367(4) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C15 C16 1.286(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9300 . ?
C16 H16B 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
C21 O2 C24 117.9(2) . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 123.1(2) . . ?
C1 C6 C7 118.3(2) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 Br1 120.0(2) . . ?
C2 C3 Br1 119.6(2) . . ?
C7 N1 C8 124.6(2) . . ?
C7 N1 C17 125.2(2) . . ?
C8 N1 C17 109.67(19) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C8 C13 C12 119.6(3) . . ?
C8 C13 C14 110.9(2) . . ?
C12 C13 C14 129.6(3) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C21 C20 C19 119.8(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
O2 C21 C22 115.8(2) . . ?
O2 C21 C20 124.9(2) . . ?
C22 C21 C20 119.3(2) . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C23 C18 C19 117.7(2) . . ?
C23 C18 C17 119.2(2) . . ?
C19 C18 C17 123.1(2) . . ?
N1 C17 C18 112.5(2) . . ?
N1 C17 C14 103.28(19) . . ?
C18 C17 C14 112.02(19) . . ?
N1 C17 H17 109.6 . . ?
C18 C17 H17 109.6 . . ?
C14 C17 H17 109.6 . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C18 C19 C20 121.6(2) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
O1 C7 N1 121.2(3) . . ?
O1 C7 C6 119.9(2) . . ?
N1 C7 C6 118.8(2) . . ?
C18 C23 C22 121.2(2) . . ?
C18 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C2 C1 C6 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C13 C14 C15 112.4(2) . . ?
C13 C14 C17 102.4(2) . . ?
C15 C14 C17 112.5(2) . . ?
C13 C14 H14 109.8 . . ?
C15 C14 H14 109.8 . . ?
C17 C14 H14 109.8 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C8 C9 121.5(3) . . ?
C13 C8 N1 109.2(2) . . ?
C9 C8 N1 129.3(3) . . ?
C9 C10 C11 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C11 C12 C13 118.9(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 C15 C14 125.0(3) . . ?
C16 C15 H15 117.5 . . ?
C14 C15 H15 117.5 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?

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 C6 C5 C4 -0.9(4) . . . . ?
C7 C6 C5 C4 173.2(2) . . . . ?
C6 C5 C4 C3 0.3(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
Br1 C3 C4 C5 -178.92(19) . . . . ?
C24 O2 C21 C22 179.5(3) . . . . ?
C24 O2 C21 C20 -2.3(4) . . . . ?
C19 C20 C21 O2 -176.9(2) . . . . ?
C19 C20 C21 C22 1.2(4) . . . . ?
O2 C21 C22 C23 176.8(2) . . . . ?
C20 C21 C22 C23 -1.6(4) . . . . ?
C7 N1 C17 C18 -87.9(3) . . . . ?
C8 N1 C17 C18 100.0(2) . . . . ?
C7 N1 C17 C14 151.1(2) . . . . ?
C8 N1 C17 C14 -21.0(3) . . . . ?
C23 C18 C17 N1 159.4(2) . . . . ?
C19 C18 C17 N1 -22.0(3) . . . . ?
C23 C18 C17 C14 -84.7(3) . . . . ?
C19 C18 C17 C14 93.8(3) . . . . ?
C4 C3 C2 C1 -1.0(4) . . . . ?
Br1 C3 C2 C1 178.6(2) . . . . ?
C23 C18 C19 C20 -2.8(4) . . . . ?
C17 C18 C19 C20 178.7(2) . . . . ?
C21 C20 C19 C18 1.0(4) . . . . ?
C8 N1 C7 O1 -7.3(4) . . . . ?
C17 N1 C7 O1 -178.3(3) . . . . ?
C8 N1 C7 C6 171.3(2) . . . . ?
C17 N1 C7 C6 0.4(4) . . . . ?
C5 C6 C7 O1 -112.9(3) . . . . ?
C1 C6 C7 O1 61.2(3) . . . . ?
C5 C6 C7 N1 68.4(3) . . . . ?
C1 C6 C7 N1 -117.5(3) . . . . ?
C19 C18 C23 C22 2.5(4) . . . . ?
C17 C18 C23 C22 -178.9(2) . . . . ?
C21 C22 C23 C18 -0.3(4) . . . . ?
C3 C2 C1 C6 0.4(4) . . . . ?
C5 C6 C1 C2 0.5(4) . . . . ?
C7 C6 C1 C2 -173.9(2) . . . . ?
C8 C13 C14 C15 107.7(3) . . . . ?
C12 C13 C14 C15 -70.6(4) . . . . ?
C8 C13 C14 C17 -13.3(3) . . . . ?
C12 C13 C14 C17 168.4(3) . . . . ?
N1 C17 C14 C13 19.9(3) . . . . ?
C18 C17 C14 C13 -101.4(2) . . . . ?
N1 C17 C14 C15 -101.0(3) . . . . ?
C18 C17 C14 C15 137.7(2) . . . . ?
C12 C13 C8 C9 -0.3(4) . . . . ?
C14 C13 C8 C9 -178.9(2) . . . . ?
C12 C13 C8 N1 179.2(2) . . . . ?
C14 C13 C8 N1 0.7(3) . . . . ?
C7 N1 C8 C13 -158.7(2) . . . . ?
C17 N1 C8 C13 13.4(3) . . . . ?
C7 N1 C8 C9 20.8(4) . . . . ?
C17 N1 C8 C9 -167.1(3) . . . . ?
C12 C11 C10 C9 -1.3(5) . . . . ?
C11 C10 C9 C8 1.1(4) . . . . ?
C13 C8 C9 C10 -0.3(4) . . . . ?
N1 C8 C9 C10 -179.8(3) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C8 C13 C12 C11 0.2(4) . . . . ?
C14 C13 C12 C11 178.4(3) . . . . ?
C13 C14 C15 C16 122.7(3) . . . . ?
C17 C14 C15 C16 -122.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_20120827guot_0m
_database_code_depnum_ccdc_archive 'CCDC 1573459'
_audit_update_record             
;
2017-09-08 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 Br N O2'
_chemical_formula_weight         448.35

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           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                   7.297(2)
_cell_length_b                   10.159(3)
_cell_length_c                   14.198(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.465(4)
_cell_angle_gamma                90.00
_cell_volume                     1043.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1084
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      19.57

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    1.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5973
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5383
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0879
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3326
_reflns_number_gt                2100
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0119P)²+0.6048P] 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
_chemical_absolute_configuration rm
_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   0.022(15)
_refine_ls_number_reflns         3326
_refine_ls_number_parameters     264
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.91503(12) 0.06380(12) -0.07220(5) 0.1058(4) Uani 1 1 d . . .
C18 C 0.4284(6) 0.0579(6) 0.3045(3) 0.0390(11) Uani 1 1 d . . .
H18 H 0.5155 0.0817 0.2602 0.047 Uiso 1 1 calc R . .
C15 C 0.4291(7) 0.0685(8) 0.5618(4) 0.0630(15) Uani 1 1 d . . .
H15A H 0.3553 0.0395 0.6063 0.076 Uiso 1 1 calc R . .
H15B H 0.5153 0.1349 0.5775 0.076 Uiso 1 1 calc R . .
C16 C 0.5350(6) 0.0589(7) 0.4049(3) 0.0446(11) Uani 1 1 d . . .
H16 H 0.5750 0.1493 0.4205 0.054 Uiso 1 1 calc R . .
N1 N 0.3661(5) -0.0780(4) 0.2823(3) 0.0410(11) Uani 1 1 d . . .
C4 C 0.5961(8) 0.0540(8) 0.0238(4) 0.0628(15) Uani 1 1 d . . .
H4 H 0.5522 0.1234 -0.0154 0.075 Uiso 1 1 calc R . .
O2 O -0.1482(6) 0.4372(4) 0.2445(3) 0.0609(11) Uani 1 1 d . . .
C13 C 0.2792(7) -0.0909(5) 0.4432(4) 0.0422(13) Uani 1 1 d . . .
C8 C 0.2590(7) -0.1357(5) 0.3499(4) 0.0399(13) Uani 1 1 d . . .
C7 C 0.4514(7) -0.1584(6) 0.2236(4) 0.0461(13) Uani 1 1 d . . .
C23 C 0.1505(8) 0.3742(6) 0.3074(5) 0.0550(17) Uani 1 1 d . . .
H23 H 0.1690 0.4591 0.3313 0.066 Uiso 1 1 calc R . .
C9 C 0.1310(8) -0.2349(6) 0.3204(5) 0.0532(17) Uani 1 1 d . . .
H9 H 0.1170 -0.2634 0.2576 0.064 Uiso 1 1 calc R . .
C21 C -0.0415(8) 0.2134(6) 0.2220(4) 0.0573(15) Uani 1 1 d . . .
H21 H -0.1535 0.1888 0.1877 0.069 Uiso 1 1 calc R . .
C19 C 0.2680(7) 0.1543(5) 0.2893(4) 0.0382(12) Uani 1 1 d . . .
C3 C 0.7656(9) -0.0018(6) 0.0150(4) 0.0629(17) Uani 1 1 d . . .
C24 C 0.2900(8) 0.2819(6) 0.3229(4) 0.0498(16) Uani 1 1 d . . .
H24 H 0.4023 0.3063 0.3570 0.060 Uiso 1 1 calc R . .
C20 C 0.0999(7) 0.1235(6) 0.2387(4) 0.0543(15) Uani 1 1 d . . .
H20 H 0.0810 0.0386 0.2148 0.065 Uiso 1 1 calc R . .
O1 O 0.4440(6) -0.2779(4) 0.2268(3) 0.0705(12) Uani 1 1 d . . .
C22 C -0.0175(8) 0.3396(6) 0.2561(4) 0.0481(14) Uani 1 1 d . . .
C6 C 0.5548(7) -0.0967(5) 0.1509(4) 0.0448(14) Uani 1 1 d . . .
C14 C 0.4112(7) 0.0148(5) 0.4755(4) 0.0441(14) Uani 1 1 d . . .
C12 C 0.1693(7) -0.1495(6) 0.5049(4) 0.0520(15) Uani 1 1 d . . .
H12 H 0.1797 -0.1210 0.5676 0.062 Uiso 1 1 calc R . .
C2 C 0.8272(9) -0.1063(6) 0.0718(5) 0.0664(18) Uani 1 1 d . . .
H2 H 0.9403 -0.1452 0.0654 0.080 Uiso 1 1 calc R . .
C17 C 0.7072(7) -0.0293(6) 0.4109(4) 0.0592(16) Uani 1 1 d . . .
H17A H 0.7765 -0.0218 0.4729 0.089 Uiso 1 1 calc R . .
H17B H 0.7827 -0.0022 0.3639 0.089 Uiso 1 1 calc R . .
H17C H 0.6699 -0.1192 0.3996 0.089 Uiso 1 1 calc R . .
C5 C 0.4918(8) 0.0066(6) 0.0908(4) 0.0565(16) Uani 1 1 d . . .
H5 H 0.3774 0.0444 0.0959 0.068 Uiso 1 1 calc R . .
C1 C 0.7224(8) -0.1534(6) 0.1380(4) 0.0567(15) Uani 1 1 d . . .
H1 H 0.7650 -0.2253 0.1751 0.068 Uiso 1 1 calc R . .
C11 C 0.0453(8) -0.2488(6) 0.4753(5) 0.0563(16) Uani 1 1 d . . .
H11 H -0.0249 -0.2872 0.5182 0.068 Uiso 1 1 calc R . .
C10 C 0.0264(8) -0.2903(6) 0.3831(5) 0.0576(16) Uani 1 1 d . . .
H10 H -0.0579 -0.3563 0.3629 0.069 Uiso 1 1 calc R . .
C25 C -0.3176(9) 0.4079(8) 0.1875(5) 0.082(2) Uani 1 1 d . . .
H25A H -0.2938 0.3837 0.1249 0.123 Uiso 1 1 calc R . .
H25B H -0.3963 0.4840 0.1838 0.123 Uiso 1 1 calc R . .
H25C H -0.3773 0.3362 0.2153 0.123 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 C3 1.876(6) . ?
C18 N1 1.475(7) . ?
C18 C19 1.520(7) . ?
C18 C16 1.533(6) . ?
C18 H18 0.9800 . ?
C15 C14 1.332(7) . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 C14 1.502(7) . ?
C16 C17 1.537(7) . ?
C16 H16 0.9800 . ?
N1 C7 1.372(7) . ?
N1 C8 1.439(7) . ?
C4 C3 1.381(8) . ?
C4 C5 1.379(8) . ?
C4 H4 0.9300 . ?
O2 C22 1.371(6) . ?
O2 C25 1.418(7) . ?
C13 C8 1.390(7) . ?
C13 C12 1.395(7) . ?
C13 C14 1.475(7) . ?
C8 C9 1.401(8) . ?
C7 O1 1.217(7) . ?
C7 C6 1.494(8) . ?
C23 C24 1.380(8) . ?
C23 C22 1.387(8) . ?
C23 H23 0.9300 . ?
C9 C10 1.367(9) . ?
C9 H9 0.9300 . ?
C21 C20 1.376(8) . ?
C21 C22 1.373(8) . ?
C21 H21 0.9300 . ?
C19 C24 1.384(8) . ?
C19 C20 1.375(7) . ?
C3 C2 1.373(8) . ?
C24 H24 0.9300 . ?
C20 H20 0.9300 . ?
C6 C1 1.385(7) . ?
C6 C5 1.393(7) . ?
C12 C11 1.384(8) . ?
C12 H12 0.9300 . ?
C2 C1 1.372(8) . ?
C2 H2 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C5 H5 0.9300 . ?
C1 H1 0.9300 . ?
C11 C10 1.365(9) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
N1 C18 C19 111.3(4) . . ?
N1 C18 C16 108.1(5) . . ?
C19 C18 C16 114.5(4) . . ?
N1 C18 H18 107.6 . . ?
C19 C18 H18 107.6 . . ?
C16 C18 H18 107.6 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C14 C16 C17 110.3(5) . . ?
C14 C16 C18 110.0(4) . . ?
C17 C16 C18 111.1(4) . . ?
C14 C16 H16 108.4 . . ?
C17 C16 H16 108.4 . . ?
C18 C16 H16 108.4 . . ?
C7 N1 C8 119.4(4) . . ?
C7 N1 C18 122.3(4) . . ?
C8 N1 C18 114.7(4) . . ?
C3 C4 C5 120.0(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C22 O2 C25 117.2(5) . . ?
C8 C13 C12 117.4(5) . . ?
C8 C13 C14 121.3(5) . . ?
C12 C13 C14 121.4(5) . . ?
C13 C8 C9 120.3(5) . . ?
C13 C8 N1 120.2(5) . . ?
C9 C8 N1 119.5(5) . . ?
O1 C7 N1 123.1(5) . . ?
O1 C7 C6 118.2(5) . . ?
N1 C7 C6 118.7(5) . . ?
C24 C23 C22 119.6(5) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C10 C9 C8 120.5(6) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C20 C21 C22 120.1(5) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C24 C19 C20 116.7(5) . . ?
C24 C19 C18 120.2(5) . . ?
C20 C19 C18 123.1(4) . . ?
C4 C3 C2 119.5(6) . . ?
C4 C3 Br1 121.2(5) . . ?
C2 C3 Br1 119.2(5) . . ?
C19 C24 C23 122.1(5) . . ?
C19 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C21 C20 C19 122.5(5) . . ?
C21 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
O2 C22 C21 125.3(5) . . ?
O2 C22 C23 115.7(5) . . ?
C21 C22 C23 119.0(5) . . ?
C1 C6 C5 117.3(5) . . ?
C1 C6 C7 116.8(5) . . ?
C5 C6 C7 125.7(5) . . ?
C15 C14 C13 124.5(6) . . ?
C15 C14 C16 119.7(5) . . ?
C13 C14 C16 115.8(5) . . ?
C13 C12 C11 121.8(6) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C1 C2 C3 120.2(6) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C5 C6 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C2 C1 C6 121.7(6) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C10 C11 C12 119.7(6) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C10 C9 120.2(6) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
N1 C18 C16 C14 -60.6(5) . . . . ?
C19 C18 C16 C14 64.0(7) . . . . ?
N1 C18 C16 C17 61.9(5) . . . . ?
C19 C18 C16 C17 -173.5(5) . . . . ?
C19 C18 N1 C7 129.9(5) . . . . ?
C16 C18 N1 C7 -103.5(5) . . . . ?
C19 C18 N1 C8 -71.4(5) . . . . ?
C16 C18 N1 C8 55.1(5) . . . . ?
C12 C13 C8 C9 0.6(7) . . . . ?
C14 C13 C8 C9 -179.1(4) . . . . ?
C12 C13 C8 N1 179.0(4) . . . . ?
C14 C13 C8 N1 -0.8(7) . . . . ?
C7 N1 C8 C13 134.3(5) . . . . ?
C18 N1 C8 C13 -25.0(6) . . . . ?
C7 N1 C8 C9 -47.3(6) . . . . ?
C18 N1 C8 C9 153.4(4) . . . . ?
C8 N1 C7 O1 -1.3(8) . . . . ?
C18 N1 C7 O1 156.4(5) . . . . ?
C8 N1 C7 C6 177.2(5) . . . . ?
C18 N1 C7 C6 -25.1(7) . . . . ?
C13 C8 C9 C10 -1.0(8) . . . . ?
N1 C8 C9 C10 -179.3(5) . . . . ?
N1 C18 C19 C24 167.7(5) . . . . ?
C16 C18 C19 C24 44.8(7) . . . . ?
N1 C18 C19 C20 -15.7(7) . . . . ?
C16 C18 C19 C20 -138.6(6) . . . . ?
C5 C4 C3 C2 1.5(9) . . . . ?
C5 C4 C3 Br1 -177.8(5) . . . . ?
C20 C19 C24 C23 0.5(9) . . . . ?
C18 C19 C24 C23 177.3(5) . . . . ?
C22 C23 C24 C19 -0.5(9) . . . . ?
C22 C21 C20 C19 0.3(9) . . . . ?
C24 C19 C20 C21 -0.4(9) . . . . ?
C18 C19 C20 C21 -177.1(5) . . . . ?
C25 O2 C22 C21 -4.4(8) . . . . ?
C25 O2 C22 C23 176.2(6) . . . . ?
C20 C21 C22 O2 -179.5(5) . . . . ?
C20 C21 C22 C23 -0.2(9) . . . . ?
C24 C23 C22 O2 179.7(5) . . . . ?
C24 C23 C22 C21 0.3(9) . . . . ?
O1 C7 C6 C1 -42.6(7) . . . . ?
N1 C7 C6 C1 138.8(5) . . . . ?
O1 C7 C6 C5 132.9(6) . . . . ?
N1 C7 C6 C5 -45.8(7) . . . . ?
C8 C13 C14 C15 175.3(5) . . . . ?
C12 C13 C14 C15 -4.4(8) . . . . ?
C8 C13 C14 C16 -6.6(6) . . . . ?
C12 C13 C14 C16 173.7(5) . . . . ?
C17 C16 C14 C15 92.4(7) . . . . ?
C18 C16 C14 C15 -144.7(6) . . . . ?
C17 C16 C14 C13 -85.8(5) . . . . ?
C18 C16 C14 C13 37.1(6) . . . . ?
C8 C13 C12 C11 0.3(7) . . . . ?
C14 C13 C12 C11 -179.9(5) . . . . ?
C4 C3 C2 C1 -1.1(9) . . . . ?
Br1 C3 C2 C1 178.1(5) . . . . ?
C3 C4 C5 C6 0.4(9) . . . . ?
C1 C6 C5 C4 -2.6(8) . . . . ?
C7 C6 C5 C4 -178.0(6) . . . . ?
C3 C2 C1 C6 -1.2(9) . . . . ?
C5 C6 C1 C2 3.0(8) . . . . ?
C7 C6 C1 C2 178.8(6) . . . . ?
C13 C12 C11 C10 -1.1(8) . . . . ?
C12 C11 C10 C9 0.7(8) . . . . ?
C8 C9 C10 C11 0.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_20130415yuan_0m
_database_code_depnum_ccdc_archive 'CCDC 1573547'
_audit_update_record             
;
2017-09-09 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 Br N O2 S'
_chemical_formula_weight         450.42

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'
S S 0.1246 0.1234 '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           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                   18.851(5)
_cell_length_b                   6.6457(19)
_cell_length_c                   20.170(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.181(3)
_cell_angle_gamma                90.00
_cell_volume                     2305.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2852
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      21.04

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    1.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6535
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?

_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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12008
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.11
_diffrn_reflns_theta_max         25.51
_reflns_number_total             6602
_reflns_number_gt                4670
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0650P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0116(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         6602
_refine_ls_number_parameters     498
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.05941(4) 0.50890(12) 0.31685(4) 0.0880(3) Uani 1 1 d . . .
Br2 Br 0.22347(4) 0.57813(10) 0.19414(3) 0.0740(2) Uani 1 1 d . . .
C1 C 0.0619(3) 1.0224(12) 0.4360(3) 0.0764(19) Uani 1 1 d . . .
H1 H 0.0934 1.1313 0.4590 0.092 Uiso 1 1 calc R . .
C2 C -0.0115(5) 1.0063(18) 0.4376(4) 0.102(3) Uani 1 1 d . . .
H2 H -0.0282 1.1050 0.4606 0.122 Uiso 1 1 calc R . .
C3 C -0.0591(5) 0.845(2) 0.4052(5) 0.110(3) Uani 1 1 d . . .
H3 H -0.1075 0.8329 0.4068 0.132 Uiso 1 1 calc R . .
C4 C -0.0346(4) 0.7060(15) 0.3714(4) 0.090(2) Uani 1 1 d . . .
H4 H -0.0671 0.5979 0.3495 0.108 Uiso 1 1 calc R . .
C5 C 0.0372(3) 0.7164(11) 0.3678(3) 0.0631(16) Uani 1 1 d . . .
C6 C 0.0891(3) 0.8826(10) 0.4017(3) 0.0564(15) Uani 1 1 d . . .
C7 C 0.1696(3) 0.9027(9) 0.4008(3) 0.0532(14) Uani 1 1 d . . .
C8 C 0.2076(4) 1.1052(11) 0.4305(4) 0.0805(19) Uani 1 1 d . . .
H8A H 0.1732 1.2119 0.4043 0.121 Uiso 1 1 calc R . .
H8B H 0.2555 1.1162 0.4247 0.121 Uiso 1 1 calc R . .
H8C H 0.2179 1.1148 0.4811 0.121 Uiso 1 1 calc R . .
C9 C 0.1625(3) 0.8923(12) 0.3227(3) 0.075(2) Uani 1 1 d . . .
H9 H 0.1949 0.8001 0.3141 0.090 Uiso 1 1 calc R . .
C10 C 0.1182(4) 0.9925(13) 0.2681(3) 0.092(2) Uani 1 1 d . . .
H10A H 0.0843 1.0872 0.2730 0.110 Uiso 1 1 calc R . .
H10B H 0.1195 0.9716 0.2230 0.110 Uiso 1 1 calc R . .
C11 C 0.2237(3) 0.7293(9) 0.4480(3) 0.0466(12) Uani 1 1 d . . .
H11 H 0.1956 0.6019 0.4322 0.056 Uiso 1 1 calc R . .
C12 C 0.2998(3) 0.7104(9) 0.4406(3) 0.0492(13) Uani 1 1 d . . .
C13 C 0.3632(3) 0.8353(10) 0.4779(3) 0.0607(15) Uani 1 1 d . . .
H13 H 0.3613 0.9248 0.5126 0.073 Uiso 1 1 calc R . .
C14 C 0.4300(3) 0.8264(11) 0.4633(3) 0.0673(17) Uani 1 1 d . . .
H14 H 0.4716 0.9116 0.4880 0.081 Uiso 1 1 calc R . .
C15 C 0.4344(3) 0.6939(11) 0.4131(3) 0.0612(15) Uani 1 1 d . . .
C16 C 0.3734(3) 0.5659(11) 0.3782(3) 0.0580(15) Uani 1 1 d . . .
H16 H 0.3761 0.4739 0.3446 0.070 Uiso 1 1 calc R . .
C17 C 0.3082(3) 0.5728(10) 0.3928(3) 0.0543(13) Uani 1 1 d . . .
H17 H 0.2682 0.4815 0.3697 0.065 Uiso 1 1 calc R . .
C18 C 0.5544(4) 0.8250(16) 0.4214(5) 0.117(3) Uani 1 1 d . . .
H18A H 0.5320 0.9560 0.4067 0.175 Uiso 1 1 calc R . .
H18B H 0.5928 0.8013 0.4025 0.175 Uiso 1 1 calc R . .
H18C H 0.5784 0.8177 0.4735 0.175 Uiso 1 1 calc R . .
C19 C 0.2988(4) 0.7210(16) 0.6675(3) 0.097(3) Uani 1 1 d . . .
C20 C 0.2264(5) 0.802(2) 0.6689(5) 0.140(4) Uani 1 1 d . . .
H20A H 0.1893 0.6953 0.6599 0.210 Uiso 1 1 calc R . .
H20B H 0.2053 0.9033 0.6320 0.210 Uiso 1 1 calc R . .
H20C H 0.2376 0.8604 0.7157 0.210 Uiso 1 1 calc R . .
C21 C 0.3358(6) 0.570(2) 0.7268(3) 0.170(5) Uani 1 1 d . . .
H21A H 0.3383 0.6237 0.7718 0.255 Uiso 1 1 calc R . .
H21B H 0.3874 0.5407 0.7312 0.255 Uiso 1 1 calc R . .
H21C H 0.3055 0.4488 0.7153 0.255 Uiso 1 1 calc R . .
C22 C 0.3552(6) 0.888(2) 0.6737(4) 0.167(6) Uani 1 1 d . . .
H22A H 0.3326 0.9770 0.6329 0.251 Uiso 1 1 calc R . .
H22B H 0.4023 0.8317 0.6743 0.251 Uiso 1 1 calc R . .
H22C H 0.3665 0.9613 0.7179 0.251 Uiso 1 1 calc R . .
C23 C 0.1355(3) 0.0584(11) 0.0726(3) 0.0659(16) Uani 1 1 d . . .
H23 H 0.1517 -0.0509 0.0536 0.079 Uiso 1 1 calc R . .
C24 C 0.0587(4) 0.0708(15) 0.0625(3) 0.078(2) Uani 1 1 d . . .
H24 H 0.0243 -0.0305 0.0370 0.093 Uiso 1 1 calc R . .
C25 C 0.0329(4) 0.2249(16) 0.0886(4) 0.086(2) Uani 1 1 d . . .
H25 H -0.0192 0.2316 0.0809 0.104 Uiso 1 1 calc R . .
C26 C 0.0839(4) 0.3748(13) 0.1271(3) 0.076(2) Uani 1 1 d . . .
H26 H 0.0659 0.4825 0.1453 0.091 Uiso 1 1 calc R . .
C27 C 0.1611(3) 0.3664(9) 0.1388(3) 0.0519(14) Uani 1 1 d . . .
C28 C 0.1896(3) 0.2065(10) 0.1109(3) 0.0506(14) Uani 1 1 d . . .
C29 C 0.2743(3) 0.1956(9) 0.1172(3) 0.0495(13) Uani 1 1 d . . .
C30 C 0.2916(3) -0.0054(10) 0.0888(3) 0.0693(16) Uani 1 1 d . . .
H30A H 0.2796 -0.1150 0.1135 0.104 Uiso 1 1 calc R . .
H30B H 0.3456 -0.0107 0.0976 0.104 Uiso 1 1 calc R . .
H30C H 0.2604 -0.0158 0.0375 0.104 Uiso 1 1 calc R . .
C31 C 0.3318(3) 0.1996(11) 0.1962(3) 0.0655(16) Uani 1 1 d . . .
H31 H 0.3756 0.2801 0.2073 0.079 Uiso 1 1 calc R . .
C32 C 0.3269(5) 0.1065(14) 0.2480(4) 0.103(2) Uani 1 1 d . . .
H32A H 0.2843 0.0239 0.2400 0.123 Uiso 1 1 calc R . .
H32B H 0.3658 0.1199 0.2947 0.123 Uiso 1 1 calc R . .
C33 C 0.2854(3) 0.3725(9) 0.0716(2) 0.0451(12) Uani 1 1 d . . .
H33 H 0.2708 0.4976 0.0885 0.054 Uiso 1 1 calc R . .
C34 C 0.3677(3) 0.3971(9) 0.0767(3) 0.0472(13) Uani 1 1 d . . .
C35 C 0.3955(3) 0.2884(10) 0.0349(3) 0.0590(15) Uani 1 1 d . . .
H35 H 0.3620 0.2018 -0.0002 0.071 Uiso 1 1 calc R . .
C36 C 0.4720(3) 0.3032(11) 0.0431(3) 0.0653(17) Uani 1 1 d . . .
H36 H 0.4893 0.2265 0.0141 0.078 Uiso 1 1 calc R . .
C37 C 0.5215(3) 0.4298(11) 0.0936(3) 0.0628(16) Uani 1 1 d . . .
C38 C 0.4941(3) 0.5489(10) 0.1343(3) 0.0612(15) Uani 1 1 d . . .
H38 H 0.5269 0.6410 0.1674 0.073 Uiso 1 1 calc R . .
C39 C 0.4184(3) 0.5306(9) 0.1257(2) 0.0510(13) Uani 1 1 d . . .
H39 H 0.4007 0.6104 0.1537 0.061 Uiso 1 1 calc R . .
C40 C 0.6310(4) 0.3107(13) 0.0747(4) 0.093(2) Uani 1 1 d . . .
H40A H 0.6230 0.1778 0.0890 0.139 Uiso 1 1 calc R . .
H40B H 0.6857 0.3346 0.0904 0.139 Uiso 1 1 calc R . .
H40C H 0.6056 0.3226 0.0228 0.139 Uiso 1 1 calc R . .
C41 C 0.1522(3) 0.4126(13) -0.1439(3) 0.075(2) Uani 1 1 d . . .
C42 C 0.0869(4) 0.2932(15) -0.1389(4) 0.092(2) Uani 1 1 d . . .
H42A H 0.0498 0.2596 -0.1869 0.138 Uiso 1 1 calc R . .
H42B H 0.0619 0.3717 -0.1147 0.138 Uiso 1 1 calc R . .
H42C H 0.1072 0.1719 -0.1120 0.138 Uiso 1 1 calc R . .
C43 C 0.1218(4) 0.5866(17) -0.1984(3) 0.106(3) Uani 1 1 d . . .
H43A H 0.1649 0.6550 -0.2022 0.159 Uiso 1 1 calc R . .
H43B H 0.0934 0.6793 -0.1820 0.159 Uiso 1 1 calc R . .
H43C H 0.0882 0.5343 -0.2452 0.159 Uiso 1 1 calc R . .
C44 C 0.2060(5) 0.2737(19) -0.1618(4) 0.126(4) Uani 1 1 d . . .
H44A H 0.1780 0.2139 -0.2087 0.189 Uiso 1 1 calc R . .
H44B H 0.2250 0.1698 -0.1257 0.189 Uiso 1 1 calc R . .
H44C H 0.2491 0.3496 -0.1624 0.189 Uiso 1 1 calc R . .
N1 N 0.2364(2) 0.7634(8) 0.5244(2) 0.0587(12) Uani 1 1 d . . .
H1A H 0.2221 0.8730 0.5381 0.070 Uiso 1 1 calc R . .
N2 N 0.2298(2) 0.3391(8) -0.0051(2) 0.0536(11) Uani 1 1 d . . .
H2A H 0.2086 0.2242 -0.0207 0.064 Uiso 1 1 calc R . .
O1 O 0.4961(2) 0.6792(8) 0.3945(2) 0.0820(14) Uani 1 1 d . . .
O2 O 0.2231(3) 0.4208(9) 0.5789(3) 0.1007(16) Uani 1 1 d . . .
O3 O 0.5995(2) 0.4544(8) 0.1072(2) 0.0838(14) Uani 1 1 d . . .
O4 O 0.1587(2) 0.6805(8) -0.0436(2) 0.0827(13) Uani 1 1 d . . .
S1 S 0.27935(8) 0.5811(3) 0.58206(7) 0.0653(4) Uani 1 1 d . . .
S2 S 0.21175(7) 0.5406(3) -0.05821(7) 0.0582(4) 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 C5 1.866(7) . ?
Br2 C27 1.879(6) . ?
C1 C6 1.377(8) . ?
C1 C2 1.400(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.336(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.447(9) . ?
C6 C7 1.531(8) . ?
C7 C9 1.528(8) . ?
C7 C8 1.527(9) . ?
C7 C11 1.574(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.265(8) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 N1 1.478(6) . ?
C11 C12 1.507(7) . ?
C11 H11 0.9800 . ?
C12 C17 1.383(7) . ?
C12 C13 1.396(8) . ?
C13 C14 1.407(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(9) . ?
C14 H14 0.9300 . ?
C15 O1 1.364(7) . ?
C15 C16 1.371(8) . ?
C16 C17 1.378(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O1 1.397(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.478(11) . ?
C19 C22 1.505(14) . ?
C19 C21 1.496(14) . ?
C19 S1 1.857(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.379(8) . ?
C23 C28 1.400(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.331(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.377(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.408(8) . ?
C28 C29 1.549(7) . ?
C29 C31 1.516(8) . ?
C29 C30 1.541(8) . ?
C29 C33 1.560(8) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.252(9) . ?
C31 H31 0.9300 . ?
C32 H32A 0.9300 . ?
C32 H32B 0.9300 . ?
C33 N2 1.487(6) . ?
C33 C34 1.520(7) . ?
C33 H33 0.9800 . ?
C34 C35 1.368(7) . ?
C34 C39 1.380(7) . ?
C35 C36 1.385(7) . ?
C35 H35 0.9300 . ?
C36 C37 1.356(8) . ?
C36 H36 0.9300 . ?
C37 O3 1.391(6) . ?
C37 C38 1.384(8) . ?
C38 C39 1.371(7) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 O3 1.419(9) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.503(9) . ?
C41 C44 1.521(10) . ?
C41 C43 1.536(12) . ?
C41 S2 1.838(6) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
N1 S1 1.644(5) . ?
N1 H1A 0.8600 . ?
N2 S2 1.661(5) . ?
N2 H2A 0.8600 . ?
O2 S1 1.486(5) . ?
O4 S2 1.481(5) . ?

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 122.3(8) . . ?
C6 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 120.4(8) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.1(8) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 122.7(9) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C4 C5 C6 119.8(7) . . ?
C4 C5 Br1 115.8(6) . . ?
C6 C5 Br1 124.3(4) . . ?
C1 C6 C5 115.7(5) . . ?
C1 C6 C7 121.5(6) . . ?
C5 C6 C7 122.8(5) . . ?
C9 C7 C8 105.9(5) . . ?
C9 C7 C6 109.8(4) . . ?
C8 C7 C6 112.4(5) . . ?
C9 C7 C11 110.6(5) . . ?
C8 C7 C11 109.0(4) . . ?
C6 C7 C11 109.2(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 128.5(7) . . ?
C10 C9 H9 115.8 . . ?
C7 C9 H9 115.8 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
N1 C11 C12 111.2(4) . . ?
N1 C11 C7 107.8(4) . . ?
C12 C11 C7 114.1(4) . . ?
N1 C11 H11 107.8 . . ?
C12 C11 H11 107.8 . . ?
C7 C11 H11 107.8 . . ?
C17 C12 C13 116.9(5) . . ?
C17 C12 C11 120.6(5) . . ?
C13 C12 C11 122.5(5) . . ?
C12 C13 C14 120.3(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.9(6) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
O1 C15 C16 116.4(6) . . ?
O1 C15 C14 124.5(6) . . ?
C16 C15 C14 119.1(5) . . ?
C15 C16 C17 120.3(6) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 122.5(5) . . ?
C16 C17 H17 118.8 . . ?
C12 C17 H17 118.8 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C22 110.8(10) . . ?
C20 C19 C21 111.2(8) . . ?
C22 C19 C21 110.2(8) . . ?
C20 C19 S1 111.5(5) . . ?
C22 C19 S1 108.1(5) . . ?
C21 C19 S1 104.8(8) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 121.6(7) . . ?
C24 C23 H23 119.2 . . ?
C28 C23 H23 119.2 . . ?
C25 C24 C23 121.2(7) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 119.6(6) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 120.7(7) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 120.8(6) . . ?
C26 C27 Br2 115.6(5) . . ?
C28 C27 Br2 123.6(4) . . ?
C23 C28 C27 116.1(5) . . ?
C23 C28 C29 120.4(5) . . ?
C27 C28 C29 123.5(5) . . ?
C31 C29 C30 103.7(5) . . ?
C31 C29 C28 110.8(4) . . ?
C30 C29 C28 112.3(5) . . ?
C31 C29 C33 113.3(5) . . ?
C30 C29 C33 109.5(4) . . ?
C28 C29 C33 107.4(4) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C29 127.1(6) . . ?
C32 C31 H31 116.5 . . ?
C29 C31 H31 116.5 . . ?
C31 C32 H32A 120.0 . . ?
C31 C32 H32B 120.0 . . ?
H32A C32 H32B 120.0 . . ?
N2 C33 C34 110.6(4) . . ?
N2 C33 C29 107.0(4) . . ?
C34 C33 C29 114.9(4) . . ?
N2 C33 H33 108.0 . . ?
C34 C33 H33 108.0 . . ?
C29 C33 H33 108.0 . . ?
C35 C34 C39 117.0(4) . . ?
C35 C34 C33 122.6(5) . . ?
C39 C34 C33 120.4(5) . . ?
C34 C35 C36 122.1(5) . . ?
C34 C35 H35 118.9 . . ?
C36 C35 H35 118.9 . . ?
C37 C36 C35 119.8(5) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C36 C37 O3 124.6(6) . . ?
C36 C37 C38 119.4(5) . . ?
O3 C37 C38 115.9(5) . . ?
C39 C38 C37 119.8(5) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 C34 121.8(5) . . ?
C38 C39 H39 119.1 . . ?
C34 C39 H39 119.1 . . ?
O3 C40 H40A 109.5 . . ?
O3 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O3 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 C44 109.9(8) . . ?
C42 C41 C43 111.7(5) . . ?
C44 C41 C43 112.1(6) . . ?
C42 C41 S2 112.5(4) . . ?
C44 C41 S2 107.1(4) . . ?
C43 C41 S2 103.3(6) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C11 N1 S1 116.6(4) . . ?
C11 N1 H1A 121.7 . . ?
S1 N1 H1A 121.7 . . ?
C33 N2 S2 114.9(4) . . ?
C33 N2 H2A 122.5 . . ?
S2 N2 H2A 122.5 . . ?
C15 O1 C18 117.8(6) . . ?
C37 O3 C40 116.0(5) . . ?
O2 S1 N1 111.2(3) . . ?
O2 S1 C19 105.3(3) . . ?
N1 S1 C19 98.1(4) . . ?
O4 S2 N2 110.7(3) . . ?
O4 S2 C41 106.0(3) . . ?
N2 S2 C41 96.8(3) . . ?

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
C6 C1 C2 C3 1.2(11) . . . . ?
C1 C2 C3 C4 -1.0(12) . . . . ?
C2 C3 C4 C5 0.3(12) . . . . ?
C3 C4 C5 C6 0.2(10) . . . . ?
C3 C4 C5 Br1 -179.1(6) . . . . ?
C2 C1 C6 C5 -0.6(8) . . . . ?
C2 C1 C6 C7 -179.8(6) . . . . ?
C4 C5 C6 C1 -0.1(8) . . . . ?
Br1 C5 C6 C1 179.2(4) . . . . ?
C4 C5 C6 C7 179.1(5) . . . . ?
Br1 C5 C6 C7 -1.6(7) . . . . ?
C1 C6 C7 C9 -126.7(6) . . . . ?
C5 C6 C7 C9 54.2(7) . . . . ?
C1 C6 C7 C8 -9.2(7) . . . . ?
C5 C6 C7 C8 171.7(5) . . . . ?
C1 C6 C7 C11 111.9(6) . . . . ?
C5 C6 C7 C11 -67.2(6) . . . . ?
C8 C7 C9 C10 -70.0(10) . . . . ?
C6 C7 C9 C10 51.5(11) . . . . ?
C11 C7 C9 C10 172.1(8) . . . . ?
C9 C7 C11 N1 172.7(5) . . . . ?
C8 C7 C11 N1 56.8(6) . . . . ?
C6 C7 C11 N1 -66.3(5) . . . . ?
C9 C7 C11 C12 48.7(6) . . . . ?
C8 C7 C11 C12 -67.3(6) . . . . ?
C6 C7 C11 C12 169.6(4) . . . . ?
N1 C11 C12 C17 141.5(5) . . . . ?
C7 C11 C12 C17 -96.3(6) . . . . ?
N1 C11 C12 C13 -41.9(7) . . . . ?
C7 C11 C12 C13 80.3(6) . . . . ?
C17 C12 C13 C14 3.6(9) . . . . ?
C11 C12 C13 C14 -173.1(6) . . . . ?
C12 C13 C14 C15 -0.9(10) . . . . ?
C13 C14 C15 O1 178.3(6) . . . . ?
C13 C14 C15 C16 -1.5(10) . . . . ?
O1 C15 C16 C17 -178.9(5) . . . . ?
C14 C15 C16 C17 0.9(9) . . . . ?
C15 C16 C17 C12 2.1(9) . . . . ?
C13 C12 C17 C16 -4.3(8) . . . . ?
C11 C12 C17 C16 172.5(5) . . . . ?
C28 C23 C24 C25 0.2(9) . . . . ?
C23 C24 C25 C26 -0.6(10) . . . . ?
C24 C25 C26 C27 0.0(9) . . . . ?
C25 C26 C27 C28 1.0(8) . . . . ?
C25 C26 C27 Br2 -178.5(5) . . . . ?
C24 C23 C28 C27 0.7(8) . . . . ?
C24 C23 C28 C29 -176.1(5) . . . . ?
C26 C27 C28 C23 -1.3(7) . . . . ?
Br2 C27 C28 C23 178.2(4) . . . . ?
C26 C27 C28 C29 175.4(5) . . . . ?
Br2 C27 C28 C29 -5.1(7) . . . . ?
C23 C28 C29 C31 -124.6(6) . . . . ?
C27 C28 C29 C31 58.8(7) . . . . ?
C23 C28 C29 C30 -9.2(7) . . . . ?
C27 C28 C29 C30 174.3(5) . . . . ?
C23 C28 C29 C33 111.2(5) . . . . ?
C27 C28 C29 C33 -65.3(6) . . . . ?
C30 C29 C31 C32 -78.1(9) . . . . ?
C28 C29 C31 C32 42.6(10) . . . . ?
C33 C29 C31 C32 163.4(7) . . . . ?
C31 C29 C33 N2 175.4(4) . . . . ?
C30 C29 C33 N2 60.3(5) . . . . ?
C28 C29 C33 N2 -61.9(5) . . . . ?
C31 C29 C33 C34 52.2(6) . . . . ?
C30 C29 C33 C34 -63.0(6) . . . . ?
C28 C29 C33 C34 174.8(4) . . . . ?
N2 C33 C34 C35 -37.6(7) . . . . ?
C29 C33 C34 C35 83.8(6) . . . . ?
N2 C33 C34 C39 143.5(5) . . . . ?
C29 C33 C34 C39 -95.1(6) . . . . ?
C39 C34 C35 C36 2.9(9) . . . . ?
C33 C34 C35 C36 -176.0(6) . . . . ?
C34 C35 C36 C37 -0.5(10) . . . . ?
C35 C36 C37 O3 179.0(6) . . . . ?
C35 C36 C37 C38 -2.6(10) . . . . ?
C36 C37 C38 C39 3.2(9) . . . . ?
O3 C37 C38 C39 -178.3(5) . . . . ?
C37 C38 C39 C34 -0.7(9) . . . . ?
C35 C34 C39 C38 -2.3(8) . . . . ?
C33 C34 C39 C38 176.6(5) . . . . ?
C12 C11 N1 S1 -64.0(6) . . . . ?
C7 C11 N1 S1 170.2(3) . . . . ?
C34 C33 N2 S2 -72.3(5) . . . . ?
C29 C33 N2 S2 161.8(3) . . . . ?
C16 C15 O1 C18 171.4(7) . . . . ?
C14 C15 O1 C18 -8.3(10) . . . . ?
C36 C37 O3 C40 -11.6(9) . . . . ?
C38 C37 O3 C40 170.0(6) . . . . ?
C11 N1 S1 O2 -81.4(4) . . . . ?
C11 N1 S1 C19 168.6(4) . . . . ?
C20 C19 S1 O2 -57.4(9) . . . . ?
C22 C19 S1 O2 -179.5(7) . . . . ?
C21 C19 S1 O2 63.0(7) . . . . ?
C20 C19 S1 N1 57.3(8) . . . . ?
C22 C19 S1 N1 -64.8(8) . . . . ?
C21 C19 S1 N1 177.7(6) . . . . ?
C33 N2 S2 O4 -76.1(4) . . . . ?
C33 N2 S2 C41 173.9(4) . . . . ?
C42 C41 S2 O4 -61.3(6) . . . . ?
C44 C41 S2 O4 177.8(6) . . . . ?
C43 C41 S2 O4 59.3(5) . . . . ?
C42 C41 S2 N2 52.6(6) . . . . ?
C44 C41 S2 N2 -68.3(6) . . . . ?
C43 C41 S2 N2 173.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.51
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.122
