# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_10nova
_database_code_depnum_ccdc_archive 'CCDC 1403793'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 N2 S'
_chemical_formula_weight         446.59

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'
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   C2/c

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

_cell_length_a                   19.059(5)
_cell_length_b                   5.6470(14)
_cell_length_c                   42.733(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.669(8)
_cell_angle_gamma                90.00
_cell_volume                     4590(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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            11767
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         0.95
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4252
_reflns_number_gt                3420
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1085P)²+3.6368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4252
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1794
_refine_ls_wR_factor_gt          0.1394
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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
C1 C 0.18135(14) 0.1809(5) 0.65783(6) 0.0259(6) Uani 1 1 d . . .
H1A H 0.1985 0.0305 0.6662 0.031 Uiso 1 1 calc R . .
H1B H 0.1337 0.1562 0.6490 0.031 Uiso 1 1 calc R . .
C2 C 0.17936(14) 0.3561(5) 0.68457(6) 0.0252(6) Uani 1 1 d . . .
C3 C 0.11934(14) 0.3633(5) 0.70176(7) 0.0306(6) Uani 1 1 d . . .
H3 H 0.0809 0.2678 0.6960 0.037 Uiso 1 1 calc R . .
C4 C 0.11705(16) 0.5123(5) 0.72738(7) 0.0365(7) Uani 1 1 d . . .
H4 H 0.0775 0.5135 0.7391 0.044 Uiso 1 1 calc R . .
C5 C 0.17294(17) 0.6589(6) 0.73573(7) 0.0385(7) Uani 1 1 d . . .
H5 H 0.1707 0.7611 0.7527 0.046 Uiso 1 1 calc R . .
C6 C 0.23193(16) 0.6535(6) 0.71889(7) 0.0402(7) Uani 1 1 d . . .
H6 H 0.2698 0.7516 0.7245 0.048 Uiso 1 1 calc R . .
C7 C 0.23514(15) 0.5020(6) 0.69345(7) 0.0338(7) Uani 1 1 d . . .
H7 H 0.2754 0.4988 0.6823 0.041 Uiso 1 1 calc R . .
C8 C 0.28986(13) 0.1520(5) 0.62969(6) 0.0223(6) Uani 1 1 d . . .
C9 C 0.38458(14) -0.1040(5) 0.63800(6) 0.0276(6) Uani 1 1 d . . .
H9A H 0.4161 0.0287 0.6356 0.033 Uiso 1 1 calc R . .
H9B H 0.3787 -0.1848 0.6180 0.033 Uiso 1 1 calc R . .
C10 C 0.41717(14) -0.2714(5) 0.66208(6) 0.0249(6) Uani 1 1 d . . .
C11 C 0.40534(14) -0.2487(5) 0.69366(6) 0.0288(6) Uani 1 1 d . . .
H11 H 0.3779 -0.1247 0.7003 0.035 Uiso 1 1 calc R . .
C12 C 0.43418(14) -0.4096(5) 0.71532(6) 0.0308(6) Uani 1 1 d . . .
H12 H 0.4257 -0.3938 0.7364 0.037 Uiso 1 1 calc R . .
C13 C 0.47523(15) -0.5921(5) 0.70573(7) 0.0348(7) Uani 1 1 d . . .
H13 H 0.4934 -0.7020 0.7203 0.042 Uiso 1 1 calc R . .
C14 C 0.48964(16) -0.6137(5) 0.67462(7) 0.0357(7) Uani 1 1 d . . .
H14 H 0.5186 -0.7346 0.6682 0.043 Uiso 1 1 calc R . .
C15 C 0.46057(14) -0.4538(5) 0.65314(7) 0.0303(6) Uani 1 1 d . . .
H15 H 0.4702 -0.4683 0.6322 0.036 Uiso 1 1 calc R . .
C16 C 0.26342(13) 0.4898(5) 0.59056(6) 0.0220(5) Uani 1 1 d . . .
C17 C 0.25994(13) 0.6552(5) 0.56796(6) 0.0232(6) Uani 1 1 d . . .
H17 H 0.2216 0.7568 0.5682 0.028 Uiso 1 1 calc R . .
C18 C 0.30741(13) 0.7001(4) 0.54292(6) 0.0226(6) Uani 1 1 d . . .
C19 C 0.35780(14) 0.5406(5) 0.53353(6) 0.0257(6) Uani 1 1 d . . .
H19 H 0.3643 0.3984 0.5443 0.031 Uiso 1 1 calc R . .
C20 C 0.39839(14) 0.5888(5) 0.50854(6) 0.0290(6) Uani 1 1 d . . .
H20 H 0.4310 0.4778 0.5026 0.035 Uiso 1 1 calc R . .
C21 C 0.39086(15) 0.8014(5) 0.49232(6) 0.0306(6) Uani 1 1 d . . .
H21 H 0.4185 0.8353 0.4757 0.037 Uiso 1 1 calc R . .
C22 C 0.34111(15) 0.9620(5) 0.50152(6) 0.0310(6) Uani 1 1 d . . .
H22 H 0.3353 1.1050 0.4909 0.037 Uiso 1 1 calc R . .
C23 C 0.29991(14) 0.9129(5) 0.52629(6) 0.0269(6) Uani 1 1 d . . .
H23 H 0.2668 1.0232 0.5320 0.032 Uiso 1 1 calc R . .
C24 C 0.20785(13) 0.4658(5) 0.61449(6) 0.0220(5) Uani 1 1 d . . .
H24 H 0.2113 0.6028 0.6286 0.026 Uiso 1 1 calc R . .
C25 C 0.13349(13) 0.4555(4) 0.59901(6) 0.0217(5) Uani 1 1 d . . .
C26 C 0.08653(14) 0.6372(5) 0.60251(6) 0.0251(6) Uani 1 1 d . . .
H26 H 0.0998 0.7667 0.6150 0.030 Uiso 1 1 calc R . .
C27 C 0.01936(14) 0.6299(5) 0.58762(6) 0.0281(6) Uani 1 1 d . . .
H27 H -0.0114 0.7558 0.5898 0.034 Uiso 1 1 calc R . .
C28 C -0.00171(13) 0.4362(5) 0.56967(6) 0.0258(6) Uani 1 1 d . . .
H28 H -0.0468 0.4294 0.5601 0.031 Uiso 1 1 calc R . .
C29 C 0.04526(14) 0.2519(5) 0.56616(6) 0.0272(6) Uani 1 1 d . . .
H29 H 0.0317 0.1209 0.5540 0.033 Uiso 1 1 calc R . .
C30 C 0.11237(14) 0.2621(5) 0.58065(6) 0.0248(6) Uani 1 1 d . . .
H30 H 0.1436 0.1381 0.5781 0.030 Uiso 1 1 calc R . .
N1 N 0.22512(11) 0.2527(4) 0.63271(5) 0.0251(5) Uani 1 1 d . . .
N2 N 0.31617(11) -0.0146(4) 0.64655(5) 0.0240(5) Uani 1 1 d . . .
S1 S 0.33036(3) 0.28179(12) 0.597266(15) 0.0248(2) 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
C1 N1 1.459(3) . ?
C1 C2 1.514(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.379(4) . ?
C2 C3 1.399(4) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N2 1.269(3) . ?
C8 N1 1.372(3) . ?
C8 S1 1.786(3) . ?
C9 N2 1.466(3) . ?
C9 C10 1.502(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.388(4) . ?
C10 C15 1.390(4) . ?
C11 C12 1.385(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.342(4) . ?
C16 C24 1.525(3) . ?
C16 S1 1.745(3) . ?
C17 C18 1.467(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.394(4) . ?
C18 C23 1.399(4) . ?
C19 C20 1.385(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.387(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 N1 1.459(3) . ?
C24 C25 1.526(3) . ?
C24 H24 0.9800 . ?
C25 C26 1.376(4) . ?
C25 C30 1.389(4) . ?
C26 C27 1.393(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.381(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.387(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.386(4) . ?
C29 H29 0.9300 . ?
C30 H30 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
N1 C1 C2 114.7(2) . . ?
N1 C1 H1A 108.6 . . ?
C2 C1 H1A 108.6 . . ?
N1 C1 H1B 108.6 . . ?
C2 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C7 C2 C3 118.7(3) . . ?
C7 C2 C1 122.8(2) . . ?
C3 C2 C1 118.4(2) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 120.8(3) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N2 C8 N1 125.4(2) . . ?
N2 C8 S1 124.8(2) . . ?
N1 C8 S1 109.81(18) . . ?
N2 C9 C10 112.4(2) . . ?
N2 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C15 118.2(3) . . ?
C11 C10 C9 121.5(2) . . ?
C15 C10 C9 120.4(2) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C10 121.6(3) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C17 C16 C24 122.7(2) . . ?
C17 C16 S1 126.1(2) . . ?
C24 C16 S1 111.22(18) . . ?
C16 C17 C18 129.9(2) . . ?
C16 C17 H17 115.1 . . ?
C18 C17 H17 115.1 . . ?
C19 C18 C23 117.3(2) . . ?
C19 C18 C17 124.5(2) . . ?
C23 C18 C17 118.1(2) . . ?
C20 C19 C18 121.6(3) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 118.3(3) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C23 C22 C21 121.1(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C18 121.0(3) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
N1 C24 C16 106.8(2) . . ?
N1 C24 C25 111.8(2) . . ?
C16 C24 C25 112.2(2) . . ?
N1 C24 H24 108.6 . . ?
C16 C24 H24 108.6 . . ?
C25 C24 H24 108.6 . . ?
C26 C25 C30 118.7(2) . . ?
C26 C25 C24 121.1(2) . . ?
C30 C25 C24 120.1(2) . . ?
C25 C26 C27 120.9(2) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C28 C27 C26 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 119.2(2) . . ?
C27 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
C30 C29 C28 120.3(2) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C25 120.7(2) . . ?
C29 C30 H30 119.6 . . ?
C25 C30 H30 119.6 . . ?
C8 N1 C1 120.9(2) . . ?
C8 N1 C24 117.7(2) . . ?
C1 N1 C24 120.1(2) . . ?
C8 N2 C9 116.0(2) . . ?
C16 S1 C8 93.20(12) . . ?

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 C1 C2 C7 -30.7(4) . . . . ?
N1 C1 C2 C3 151.9(2) . . . . ?
C7 C2 C3 C4 -0.9(4) . . . . ?
C1 C2 C3 C4 176.6(2) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
C1 C2 C7 C6 -177.5(3) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
N2 C9 C10 C11 -31.1(3) . . . . ?
N2 C9 C10 C15 149.2(2) . . . . ?
C15 C10 C11 C12 -2.3(4) . . . . ?
C9 C10 C11 C12 178.0(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 C14 1.7(4) . . . . ?
C12 C13 C14 C15 -1.9(5) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?
C11 C10 C15 C14 2.0(4) . . . . ?
C9 C10 C15 C14 -178.2(3) . . . . ?
C24 C16 C17 C18 -178.6(2) . . . . ?
S1 C16 C17 C18 2.7(4) . . . . ?
C16 C17 C18 C19 15.7(4) . . . . ?
C16 C17 C18 C23 -167.1(3) . . . . ?
C23 C18 C19 C20 -0.7(4) . . . . ?
C17 C18 C19 C20 176.4(2) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C18 0.3(4) . . . . ?
C19 C18 C23 C22 0.0(4) . . . . ?
C17 C18 C23 C22 -177.3(2) . . . . ?
C17 C16 C24 N1 173.7(2) . . . . ?
S1 C16 C24 N1 -7.4(2) . . . . ?
C17 C16 C24 C25 50.9(3) . . . . ?
S1 C16 C24 C25 -130.26(19) . . . . ?
N1 C24 C25 C26 128.2(2) . . . . ?
C16 C24 C25 C26 -111.9(3) . . . . ?
N1 C24 C25 C30 -52.7(3) . . . . ?
C16 C24 C25 C30 67.2(3) . . . . ?
C30 C25 C26 C27 -0.9(4) . . . . ?
C24 C25 C26 C27 178.2(2) . . . . ?
C25 C26 C27 C28 1.6(4) . . . . ?
C26 C27 C28 C29 -1.3(4) . . . . ?
C27 C28 C29 C30 0.3(4) . . . . ?
C28 C29 C30 C25 0.4(4) . . . . ?
C26 C25 C30 C29 -0.1(4) . . . . ?
C24 C25 C30 C29 -179.2(2) . . . . ?
N2 C8 N1 C1 3.6(4) . . . . ?
S1 C8 N1 C1 -178.94(19) . . . . ?
N2 C8 N1 C24 170.9(2) . . . . ?
S1 C8 N1 C24 -11.7(3) . . . . ?
C2 C1 N1 C8 104.4(3) . . . . ?
C2 C1 N1 C24 -62.6(3) . . . . ?
C16 C24 N1 C8 12.4(3) . . . . ?
C25 C24 N1 C8 135.5(2) . . . . ?
C16 C24 N1 C1 179.8(2) . . . . ?
C25 C24 N1 C1 -57.1(3) . . . . ?
N1 C8 N2 C9 176.6(2) . . . . ?
S1 C8 N2 C9 -0.4(3) . . . . ?
C10 C9 N2 C8 170.6(2) . . . . ?
C17 C16 S1 C8 -179.7(2) . . . . ?
C24 C16 S1 C8 1.43(19) . . . . ?
N2 C8 S1 C16 -177.1(2) . . . . ?
N1 C8 S1 C16 5.46(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1403803'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-07-28 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         'C30 H23 Br N2 O S'
_chemical_formula_sum            'C30 H23 Br N2 O S'
_chemical_formula_weight         539.47

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   9.724(5)
_cell_length_b                   11.581(5)
_cell_length_c                   11.774(5)
_cell_angle_alpha                75.443(5)
_cell_angle_beta                 87.986(5)
_cell_angle_gamma                89.040(5)
_cell_volume                     1282.5(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      25.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   0.705
_exptl_transmission_factor_max   0.761
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.710
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13366
_diffrn_reflns_av_unetI/netI     0.2088
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.240
_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 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             9327
_reflns_number_gt                5260
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.953

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1648 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.108(9)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         9327
_refine_ls_number_parameters     611
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1707
_refine_ls_R_factor_gt           0.0884
_refine_ls_wR_factor_ref         0.1736
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.07678(17) -0.78772(13) 0.88633(13) 0.0479(6) Uani 1 1 d . . . . .
Br2 Br -0.38731(19) 0.06913(17) -0.08872(15) 0.0654(7) Uani 1 1 d . . . . .
S1 S -0.1098(4) -0.2212(3) 0.3511(3) 0.0243(9) Uani 1 1 d . . . . .
S2 S -0.6532(3) -0.4429(3) 0.4787(3) 0.0234(9) Uani 1 1 d . . . . .
O1 O -0.0163(10) -0.1564(9) 0.1318(8) 0.038(3) Uani 1 1 d . . . . .
O2 O -0.5671(10) -0.5335(8) 0.6890(8) 0.038(3) Uani 1 1 d . . . . .
N1 N -0.0979(11) -0.3493(9) 0.1852(10) 0.024(3) Uani 1 1 d . . . . .
N2 N -0.1810(11) -0.4396(9) 0.3715(9) 0.021(3) Uani 1 1 d . . . . .
N3 N -0.5702(11) -0.3265(10) 0.6413(9) 0.025(3) Uani 1 1 d . . . . .
N4 N -0.6462(11) -0.2157(10) 0.4622(9) 0.018(3) Uani 1 1 d . . . . .
C1 C -0.0357(14) -0.2517(13) 0.1095(12) 0.029(4) Uani 1 1 d . . . . .
C2 C 0.0136(14) -0.2747(12) -0.0038(11) 0.025(3) Uani 1 1 d . . . . .
C3 C -0.0281(16) -0.3721(14) -0.0386(12) 0.038(4) Uani 1 1 d . . . . .
H3A H -0.0933 -0.4250 0.0084 0.046 Uiso 1 1 calc R U . . .
C4 C 0.0244(16) -0.3942(15) -0.1426(13) 0.039(4) Uani 1 1 d . . . . .
H4A H -0.0068 -0.4615 -0.1666 0.047 Uiso 1 1 calc R U . . .
C5 C 0.1186(16) -0.3218(14) -0.2099(14) 0.037(4) Uani 1 1 d . U . . .
H5A H 0.1546 -0.3381 -0.2803 0.044 Uiso 1 1 calc R U . . .
C6 C 0.1631(15) -0.2213(14) -0.1741(13) 0.031(4) Uani 1 1 d . . . . .
H6A H 0.2292 -0.1694 -0.2211 0.037 Uiso 1 1 calc R U . . .
C7 C 0.1118(16) -0.1979(14) -0.0722(13) 0.035(4) Uani 1 1 d . . . . .
H7A H 0.1424 -0.1304 -0.0483 0.042 Uiso 1 1 calc R U . . .
C8 C -0.1252(15) -0.3445(13) 0.2912(14) 0.030(4) Uani 1 1 d . . . . .
C9 C -0.2138(14) -0.5490(12) 0.3424(11) 0.023(3) Uani 1 1 d . . . . .
C10 C -0.3430(14) -0.5978(12) 0.3725(12) 0.030(4) Uani 1 1 d . . . . .
H11A H -0.4073 -0.5617 0.4159 0.036 Uiso 1 1 calc R U . . .
C11 C -0.3779(15) -0.6995(12) 0.3392(11) 0.031(4) Uani 1 1 d . . . . .
H12A H -0.4654 -0.7345 0.3622 0.037 Uiso 1 1 calc R U . . .
C12 C -0.2875(15) -0.7509(13) 0.2727(12) 0.028(4) Uani 1 1 d . . . . .
C13 C -0.1578(16) -0.7043(13) 0.2480(13) 0.034(4) Uani 1 1 d . . . . .
H14A H -0.0935 -0.7423 0.2063 0.040 Uiso 1 1 calc R U . . .
C14 C -0.1167(15) -0.6031(12) 0.2819(12) 0.027(4) Uani 1 1 d . . . . .
H15A H -0.0263 -0.5724 0.2645 0.033 Uiso 1 1 calc R U . . .
C15 C -0.3297(18) -0.8591(13) 0.2326(14) 0.050(5) Uani 1 1 d . . . . .
H15B H -0.4252 -0.8791 0.2582 0.076 Uiso 1 1 calc R U . . .
H15C H -0.3216 -0.8415 0.1468 0.076 Uiso 1 1 calc R U . . .
H15D H -0.2695 -0.9267 0.2669 0.076 Uiso 1 1 calc R U . . .
C16 C -0.2149(14) -0.4251(12) 0.4912(11) 0.020(3) Uani 1 1 d . . . . .
H17A H -0.3165 -0.4343 0.5056 0.025 Uiso 1 1 calc R U . . .
C17 C -0.1432(15) -0.5179(12) 0.5869(12) 0.024(4) Uani 1 1 d . . . . .
C18 C -0.2201(15) -0.5884(13) 0.6795(12) 0.027(4) Uani 1 1 d . . . . .
H19A H -0.3177 -0.5817 0.6812 0.032 Uiso 1 1 calc R U . . .
C19 C -0.1547(16) -0.6682(12) 0.7692(12) 0.031(4) Uani 1 1 d . . . . .
H20A H -0.2073 -0.7163 0.8326 0.037 Uiso 1 1 calc R U . . .
C20 C -0.0141(16) -0.6779(12) 0.7666(11) 0.028(4) Uani 1 1 d . . . . .
C21 C 0.0648(15) -0.6093(13) 0.6706(13) 0.028(4) Uani 1 1 d . . . . .
H22A H 0.1621 -0.6174 0.6674 0.033 Uiso 1 1 calc R U . . .
C22 C -0.0028(15) -0.5302(12) 0.5816(12) 0.030(4) Uani 1 1 d . . . . .
H23A H 0.0486 -0.4840 0.5162 0.036 Uiso 1 1 calc R U . . .
C23 C -0.1779(14) -0.3002(12) 0.4923(12) 0.024(4) Uiso 1 1 d . . . . .
C24 C -0.1905(13) -0.2529(12) 0.5836(11) 0.024(3) Uani 1 1 d . . . . .
H25A H -0.2280 -0.3048 0.6530 0.028 Uiso 1 1 calc R U . . .
C25 C -0.1562(13) -0.1332(13) 0.5954(13) 0.026(4) Uani 1 1 d . . . . .
C26 C -0.1521(16) -0.1199(14) 0.7121(13) 0.040(4) Uani 1 1 d . . . . .
H27A H -0.1710 -0.1854 0.7774 0.047 Uiso 1 1 calc R U . . .
C27 C -0.1197(16) -0.0075(15) 0.7283(16) 0.048(5) Uani 1 1 d . . . . .
H28A H -0.1156 0.0025 0.8057 0.057 Uiso 1 1 calc R U . . .
C28 C -0.0938(15) 0.0880(16) 0.6345(15) 0.040(4) Uani 1 1 d . . . . .
H29A H -0.0695 0.1630 0.6466 0.048 Uiso 1 1 calc R U . . .
C29 C -0.1033(16) 0.0736(14) 0.5247(15) 0.037(4) Uani 1 1 d . . . . .
H30A H -0.0897 0.1407 0.4598 0.045 Uiso 1 1 calc R U . . .
C30 C -0.1320(14) -0.0344(14) 0.5041(13) 0.030(4) Uani 1 1 d . . . . .
H31A H -0.1353 -0.0413 0.4255 0.036 Uiso 1 1 calc R U . . .
C31 C -0.5472(13) -0.4384(13) 0.7140(12) 0.024(3) Uani 1 1 d . . . . .
C32 C -0.4918(14) -0.4350(14) 0.8268(12) 0.029(4) Uani 1 1 d . . . . .
C33 C -0.4709(15) -0.3280(15) 0.8557(12) 0.034(4) Uani 1 1 d . . . . .
H34A H -0.4886 -0.2541 0.8011 0.041 Uiso 1 1 calc R U . . .
C34 C -0.4224(17) -0.3313(15) 0.9681(15) 0.047(5) Uani 1 1 d . . . . .
H35A H -0.4122 -0.2589 0.9909 0.056 Uiso 1 1 calc R U . . .
C35 C -0.3905(17) -0.4362(16) 1.0435(15) 0.045(5) Uiso 1 1 d . . . . .
H36A H -0.3533 -0.4362 1.1170 0.054 Uiso 1 1 calc R U . . .
C36 C -0.4106(17) -0.5419(16) 1.0161(14) 0.048(5) Uani 1 1 d . . . . .
H37A H -0.3886 -0.6149 1.0706 0.057 Uiso 1 1 calc R U . . .
C37 C -0.4628(16) -0.5431(16) 0.9090(13) 0.044(5) Uani 1 1 d . . . . .
H38A H -0.4793 -0.6169 0.8906 0.053 Uiso 1 1 calc R U . . .
C38 C -0.6191(14) -0.3206(14) 0.5371(13) 0.027(4) Uani 1 1 d . . . . .
C39 C -0.6324(13) -0.1070(12) 0.4983(11) 0.019(3) Uani 1 1 d . . . . .
C40 C -0.5050(15) -0.0674(14) 0.5124(13) 0.033(4) Uani 1 1 d . . . . .
H41A H -0.4256 -0.1091 0.4942 0.040 Uiso 1 1 calc R U . . .
C41 C -0.4907(16) 0.0344(13) 0.5535(12) 0.031(4) Uani 1 1 d . . . . .
H42A H -0.4012 0.0619 0.5624 0.037 Uiso 1 1 calc R U . . .
C42 C -0.6049(15) 0.0966(12) 0.5817(12) 0.024(3) Uani 1 1 d . . . . .
C43 C -0.7314(14) 0.0556(12) 0.5652(12) 0.031(4) Uani 1 1 d . . . . .
H44A H -0.8111 0.0974 0.5825 0.037 Uiso 1 1 calc R U . . .
C44 C -0.7473(15) -0.0474(12) 0.5231(12) 0.029(4) Uiso 1 1 d . . . . .
H45A H -0.8364 -0.0746 0.5122 0.034 Uiso 1 1 calc R U . . .
C45 C -0.5889(16) 0.2053(12) 0.6252(13) 0.040(4) Uani 1 1 d . . . . .
H45B H -0.4908 0.2202 0.6313 0.060 Uiso 1 1 calc R U . . .
H45C H -0.6305 0.2738 0.5703 0.060 Uiso 1 1 calc R U . . .
H45D H -0.6347 0.1936 0.7027 0.060 Uiso 1 1 calc R U . . .
C46 C -0.7074(13) -0.2166(11) 0.3508(11) 0.018(3) Uani 1 1 d . . . . .
H47A H -0.8042 -0.1861 0.3505 0.021 Uiso 1 1 calc R U . . .
C47 C -0.6264(14) -0.1411(12) 0.2459(11) 0.021(3) Uani 1 1 d . . . . .
C48 C -0.6966(16) -0.0650(13) 0.1572(12) 0.033(4) Uani 1 1 d . . . . .
H49A H -0.7938 -0.0580 0.1640 0.040 Uiso 1 1 calc R U . . .
C49 C -0.6279(17) 0.0004(13) 0.0598(13) 0.039(4) Uani 1 1 d . . . . .
H50A H -0.6754 0.0564 0.0009 0.047 Uiso 1 1 calc R U . . .
C50 C -0.4883(18) -0.0166(13) 0.0490(13) 0.040(4) Uani 1 1 d . . . . .
C51 C -0.4130(15) -0.0921(13) 0.1343(12) 0.028(4) Uani 1 1 d . . . . .
H52A H -0.3160 -0.1001 0.1264 0.033 Uiso 1 1 calc R U . . .
C52 C -0.4869(13) -0.1560(11) 0.2325(12) 0.024(3) Uani 1 1 d . . . . .
H53A H -0.4396 -0.2115 0.2920 0.028 Uiso 1 1 calc R U . . .
C53 C -0.7080(13) -0.3490(12) 0.3469(11) 0.020(3) Uiso 1 1 d . . . . .
C54 C -0.7378(13) -0.3818(12) 0.2486(13) 0.025(4) Uani 1 1 d . . . . .
H55A H -0.7544 -0.3179 0.1820 0.030 Uiso 1 1 calc R U . . .
C55 C -0.7483(15) -0.4992(13) 0.2296(12) 0.028(4) Uani 1 1 d . . . . .
C56 C -0.7554(16) -0.6078(15) 0.3184(14) 0.037(4) Uani 1 1 d . . . . .
H57A H -0.7558 -0.6063 0.3987 0.045 Uiso 1 1 calc R U . . .
C57 C -0.7616(17) -0.7159(15) 0.2885(16) 0.044(5) Uani 1 1 d . . . . .
H58A H -0.7652 -0.7883 0.3483 0.053 Uiso 1 1 calc R U . . .
C58 C -0.7627(18) -0.7185(15) 0.1747(16) 0.049(5) Uani 1 1 d . . . . .
H59A H -0.7669 -0.7929 0.1549 0.059 Uiso 1 1 calc R U . . .
C59 C -0.7576(19) -0.6125(17) 0.0849(16) 0.054(5) Uani 1 1 d . . . . .
H60A H -0.7612 -0.6143 0.0048 0.065 Uiso 1 1 calc R U . . .
C60 C -0.7476(15) -0.5078(14) 0.1150(14) 0.037(4) Uani 1 1 d . . . . .
H61A H -0.7397 -0.4366 0.0540 0.044 Uiso 1 1 calc R U . . .


_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 C20 1.880(14) . ?
Br2 C50 1.921(15) . ?
S1 C8 1.754(16) . ?
S1 C23 1.793(14) . ?
S2 C53 1.751(13) . ?
S2 C38 1.764(16) . ?
O1 C1 1.216(15) . ?
O2 C31 1.228(15) . ?
N1 C8 1.282(17) . ?
N1 C1 1.384(15) . ?
N2 C8 1.364(16) . ?
N2 C9 1.437(16) . ?
N2 C16 1.486(15) . ?
N3 C38 1.317(17) . ?
N3 C31 1.382(16) . ?
N4 C38 1.338(17) . ?
N4 C39 1.436(16) . ?
N4 C46 1.462(15) . ?
C1 C2 1.487(18) . ?
C2 C3 1.365(19) . ?
C2 C7 1.402(18) . ?
C3 C4 1.391(19) . ?
C4 C5 1.345(19) . ?
C5 C6 1.41(2) . ?
C6 C7 1.370(19) . ?
C9 C10 1.384(17) . ?
C9 C14 1.396(18) . ?
C10 C11 1.383(17) . ?
C11 C12 1.381(19) . ?
C12 C13 1.37(2) . ?
C12 C15 1.513(19) . ?
C13 C14 1.399(19) . ?
C16 C23 1.500(18) . ?
C16 C17 1.527(18) . ?
C17 C22 1.371(18) . ?
C17 C18 1.389(18) . ?
C18 C19 1.383(19) . ?
C19 C20 1.370(19) . ?
C20 C21 1.416(19) . ?
C21 C22 1.384(19) . ?
C23 C24 1.325(17) . ?
C24 C25 1.472(18) . ?
C25 C30 1.376(19) . ?
C25 C26 1.422(19) . ?
C26 C27 1.40(2) . ?
C27 C28 1.37(2) . ?
C28 C29 1.35(2) . ?
C29 C30 1.37(2) . ?
C31 C32 1.460(19) . ?
C32 C33 1.384(19) . ?
C32 C37 1.41(2) . ?
C33 C34 1.41(2) . ?
C34 C35 1.35(2) . ?
C35 C36 1.36(2) . ?
C36 C37 1.38(2) . ?
C39 C40 1.358(18) . ?
C39 C44 1.365(18) . ?
C40 C41 1.394(19) . ?
C41 C42 1.388(19) . ?
C42 C43 1.364(18) . ?
C42 C45 1.486(18) . ?
C43 C44 1.416(18) . ?
C46 C47 1.524(17) . ?
C46 C53 1.545(17) . ?
C47 C52 1.374(17) . ?
C47 C48 1.378(19) . ?
C48 C49 1.365(19) . ?
C49 C50 1.37(2) . ?
C50 C51 1.38(2) . ?
C51 C52 1.389(18) . ?
C53 C54 1.348(18) . ?
C54 C55 1.438(19) . ?
C55 C60 1.377(19) . ?
C55 C56 1.420(19) . ?
C56 C57 1.39(2) . ?
C57 C58 1.35(2) . ?
C58 C59 1.40(2) . ?
C59 C60 1.35(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C23 93.2(6) . . ?
C53 S2 C38 91.9(7) . . ?
C8 N1 C1 118.2(12) . . ?
C8 N2 C9 122.5(12) . . ?
C8 N2 C16 117.7(11) . . ?
C9 N2 C16 119.7(10) . . ?
C38 N3 C31 117.7(13) . . ?
C38 N4 C39 120.0(11) . . ?
C38 N4 C46 118.1(11) . . ?
C39 N4 C46 121.4(11) . . ?
O1 C1 N1 125.2(13) . . ?
O1 C1 C2 121.2(12) . . ?
N1 C1 C2 113.5(12) . . ?
C3 C2 C7 119.7(13) . . ?
C3 C2 C1 121.6(12) . . ?
C7 C2 C1 118.6(12) . . ?
C2 C3 C4 120.4(14) . . ?
C5 C4 C3 121.0(16) . . ?
C4 C5 C6 119.0(15) . . ?
C7 C6 C5 120.7(14) . . ?
C6 C7 C2 119.2(14) . . ?
N1 C8 N2 121.1(13) . . ?
N1 C8 S1 127.6(11) . . ?
N2 C8 S1 111.2(11) . . ?
C10 C9 C14 120.9(13) . . ?
C10 C9 N2 119.3(12) . . ?
C14 C9 N2 119.8(12) . . ?
C11 C10 C9 119.6(13) . . ?
C12 C11 C10 121.0(14) . . ?
C13 C12 C11 118.5(14) . . ?
C13 C12 C15 121.2(14) . . ?
C11 C12 C15 120.3(14) . . ?
C12 C13 C14 122.5(14) . . ?
C9 C14 C13 117.4(13) . . ?
N2 C16 C23 107.4(10) . . ?
N2 C16 C17 112.7(11) . . ?
C23 C16 C17 112.0(12) . . ?
C22 C17 C18 120.4(13) . . ?
C22 C17 C16 119.7(12) . . ?
C18 C17 C16 119.9(13) . . ?
C19 C18 C17 120.0(14) . . ?
C20 C19 C18 120.0(14) . . ?
C19 C20 C21 120.4(13) . . ?
C19 C20 Br1 120.7(11) . . ?
C21 C20 Br1 118.8(11) . . ?
C22 C21 C20 118.7(14) . . ?
C17 C22 C21 120.6(13) . . ?
C24 C23 C16 126.0(13) . . ?
C24 C23 S1 123.5(11) . . ?
C16 C23 S1 110.4(10) . . ?
C23 C24 C25 130.8(14) . . ?
C30 C25 C26 118.3(14) . . ?
C30 C25 C24 125.6(14) . . ?
C26 C25 C24 116.1(13) . . ?
C27 C26 C25 118.4(15) . . ?
C28 C27 C26 121.3(15) . . ?
C29 C28 C27 118.9(16) . . ?
C28 C29 C30 122.1(16) . . ?
C29 C30 C25 121.0(15) . . ?
O2 C31 N3 125.4(13) . . ?
O2 C31 C32 121.4(13) . . ?
N3 C31 C32 113.2(13) . . ?
C33 C32 C37 119.4(14) . . ?
C33 C32 C31 121.5(13) . . ?
C37 C32 C31 119.1(14) . . ?
C32 C33 C34 118.5(15) . . ?
C35 C34 C33 120.7(17) . . ?
C34 C35 C36 121.2(17) . . ?
C35 C36 C37 119.9(17) . . ?
C36 C37 C32 120.1(17) . . ?
N3 C38 N4 121.3(13) . . ?
N3 C38 S2 126.0(12) . . ?
N4 C38 S2 112.6(11) . . ?
C40 C39 C44 120.7(14) . . ?
C40 C39 N4 119.5(12) . . ?
C44 C39 N4 119.7(12) . . ?
C39 C40 C41 119.9(14) . . ?
C42 C41 C40 121.3(15) . . ?
C43 C42 C41 117.4(13) . . ?
C43 C42 C45 121.6(13) . . ?
C41 C42 C45 121.0(14) . . ?
C42 C43 C44 121.9(13) . . ?
C39 C44 C43 118.7(14) . . ?
N4 C46 C47 112.1(11) . . ?
N4 C46 C53 105.5(10) . . ?
C47 C46 C53 111.0(10) . . ?
C52 C47 C48 119.3(13) . . ?
C52 C47 C46 121.2(12) . . ?
C48 C47 C46 119.1(12) . . ?
C49 C48 C47 120.7(15) . . ?
C48 C49 C50 118.5(15) . . ?
C49 C50 C51 123.2(14) . . ?
C49 C50 Br2 120.3(12) . . ?
C51 C50 Br2 116.5(13) . . ?
C50 C51 C52 116.3(14) . . ?
C47 C52 C51 121.8(13) . . ?
C54 C53 C46 121.8(12) . . ?
C54 C53 S2 126.5(11) . . ?
C46 C53 S2 111.6(9) . . ?
C53 C54 C55 129.7(14) . . ?
C60 C55 C56 116.8(14) . . ?
C60 C55 C54 117.3(13) . . ?
C56 C55 C54 125.9(14) . . ?
C57 C56 C55 120.4(15) . . ?
C58 C57 C56 120.1(15) . . ?
C57 C58 C59 120.9(16) . . ?
C60 C59 C58 118.5(17) . . ?
C59 C60 C55 123.4(16) . . ?

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
C8 N1 C1 O1 -8(2) . . . . ?
C8 N1 C1 C2 169.7(12) . . . . ?
O1 C1 C2 C3 -168.1(15) . . . . ?
N1 C1 C2 C3 15(2) . . . . ?
O1 C1 C2 C7 16(2) . . . . ?
N1 C1 C2 C7 -161.6(13) . . . . ?
C7 C2 C3 C4 -1(2) . . . . ?
C1 C2 C3 C4 -177.2(14) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C4 C5 C6 -1(2) . . . . ?
C4 C5 C6 C7 0(2) . . . . ?
C5 C6 C7 C2 0(2) . . . . ?
C3 C2 C7 C6 1(2) . . . . ?
C1 C2 C7 C6 176.9(14) . . . . ?
C1 N1 C8 N2 -177.1(13) . . . . ?
C1 N1 C8 S1 7.4(19) . . . . ?
C9 N2 C8 N1 -1(2) . . . . ?
C16 N2 C8 N1 -177.5(12) . . . . ?
C9 N2 C8 S1 175.4(10) . . . . ?
C16 N2 C8 S1 -1.3(16) . . . . ?
C23 S1 C8 N1 177.0(14) . . . . ?
C23 S1 C8 N2 1.2(11) . . . . ?
C8 N2 C9 C10 -129.9(14) . . . . ?
C16 N2 C9 C10 46.8(17) . . . . ?
C8 N2 C9 C14 48.6(19) . . . . ?
C16 N2 C9 C14 -134.7(13) . . . . ?
C14 C9 C10 C11 -2(2) . . . . ?
N2 C9 C10 C11 176.4(11) . . . . ?
C9 C10 C11 C12 -2(2) . . . . ?
C10 C11 C12 C13 5(2) . . . . ?
C10 C11 C12 C15 -177.4(13) . . . . ?
C11 C12 C13 C14 -4(2) . . . . ?
C15 C12 C13 C14 178.7(14) . . . . ?
C10 C9 C14 C13 3(2) . . . . ?
N2 C9 C14 C13 -175.2(12) . . . . ?
C12 C13 C14 C9 0(2) . . . . ?
C8 N2 C16 C23 0.7(17) . . . . ?
C9 N2 C16 C23 -176.1(11) . . . . ?
C8 N2 C16 C17 -123.1(13) . . . . ?
C9 N2 C16 C17 60.1(16) . . . . ?
N2 C16 C17 C22 55.3(17) . . . . ?
C23 C16 C17 C22 -65.9(16) . . . . ?
N2 C16 C17 C18 -125.6(13) . . . . ?
C23 C16 C17 C18 113.3(14) . . . . ?
C22 C17 C18 C19 2(2) . . . . ?
C16 C17 C18 C19 -176.8(12) . . . . ?
C17 C18 C19 C20 0(2) . . . . ?
C18 C19 C20 C21 -2(2) . . . . ?
C18 C19 C20 Br1 -178.9(10) . . . . ?
C19 C20 C21 C22 2(2) . . . . ?
Br1 C20 C21 C22 178.8(10) . . . . ?
C18 C17 C22 C21 -3(2) . . . . ?
C16 C17 C22 C21 176.5(12) . . . . ?
C20 C21 C22 C17 1(2) . . . . ?
N2 C16 C23 C24 -178.9(13) . . . . ?
C17 C16 C23 C24 -54.7(19) . . . . ?
N2 C16 C23 S1 0.2(14) . . . . ?
C17 C16 C23 S1 124.4(10) . . . . ?
C8 S1 C23 C24 178.3(13) . . . . ?
C8 S1 C23 C16 -0.8(11) . . . . ?
C16 C23 C24 C25 179.0(13) . . . . ?
S1 C23 C24 C25 0(2) . . . . ?
C23 C24 C25 C30 16(2) . . . . ?
C23 C24 C25 C26 -165.7(15) . . . . ?
C30 C25 C26 C27 -2(2) . . . . ?
C24 C25 C26 C27 179.9(13) . . . . ?
C25 C26 C27 C28 1(2) . . . . ?
C26 C27 C28 C29 2(2) . . . . ?
C27 C28 C29 C30 -3(2) . . . . ?
C28 C29 C30 C25 2(2) . . . . ?
C26 C25 C30 C29 1(2) . . . . ?
C24 C25 C30 C29 178.7(14) . . . . ?
C38 N3 C31 O2 1(2) . . . . ?
C38 N3 C31 C32 179.4(12) . . . . ?
O2 C31 C32 C33 -179.2(13) . . . . ?
N3 C31 C32 C33 2(2) . . . . ?
O2 C31 C32 C37 -1(2) . . . . ?
N3 C31 C32 C37 -179.6(12) . . . . ?
C37 C32 C33 C34 -1(2) . . . . ?
C31 C32 C33 C34 177.4(14) . . . . ?
C32 C33 C34 C35 3(2) . . . . ?
C33 C34 C35 C36 -3(3) . . . . ?
C34 C35 C36 C37 1(3) . . . . ?
C35 C36 C37 C32 2(2) . . . . ?
C33 C32 C37 C36 -2(2) . . . . ?
C31 C32 C37 C36 -180.0(14) . . . . ?
C31 N3 C38 N4 179.0(11) . . . . ?
C31 N3 C38 S2 -2.2(19) . . . . ?
C39 N4 C38 N3 -5(2) . . . . ?
C46 N4 C38 N3 -176.7(12) . . . . ?
C39 N4 C38 S2 176.1(9) . . . . ?
C46 N4 C38 S2 4.3(15) . . . . ?
C53 S2 C38 N3 -179.3(13) . . . . ?
C53 S2 C38 N4 -0.4(11) . . . . ?
C38 N4 C39 C40 71.7(17) . . . . ?
C46 N4 C39 C40 -116.9(14) . . . . ?
C38 N4 C39 C44 -105.5(15) . . . . ?
C46 N4 C39 C44 66.0(16) . . . . ?
C44 C39 C40 C41 1(2) . . . . ?
N4 C39 C40 C41 -176.5(12) . . . . ?
C39 C40 C41 C42 1(2) . . . . ?
C40 C41 C42 C43 -1(2) . . . . ?
C40 C41 C42 C45 -179.8(13) . . . . ?
C41 C42 C43 C44 1(2) . . . . ?
C45 C42 C43 C44 179.6(13) . . . . ?
C40 C39 C44 C43 -1(2) . . . . ?
N4 C39 C44 C43 176.3(12) . . . . ?
C42 C43 C44 C39 0(2) . . . . ?
C38 N4 C46 C47 -127.3(12) . . . . ?
C39 N4 C46 C47 61.0(14) . . . . ?
C38 N4 C46 C53 -6.4(15) . . . . ?
C39 N4 C46 C53 -178.0(10) . . . . ?
N4 C46 C47 C52 51.5(16) . . . . ?
C53 C46 C47 C52 -66.2(15) . . . . ?
N4 C46 C47 C48 -135.0(12) . . . . ?
C53 C46 C47 C48 107.3(14) . . . . ?
C52 C47 C48 C49 -4(2) . . . . ?
C46 C47 C48 C49 -177.4(12) . . . . ?
C47 C48 C49 C50 4(2) . . . . ?
C48 C49 C50 C51 -3(2) . . . . ?
C48 C49 C50 Br2 177.9(10) . . . . ?
C49 C50 C51 C52 3(2) . . . . ?
Br2 C50 C51 C52 -178.6(9) . . . . ?
C48 C47 C52 C51 3(2) . . . . ?
C46 C47 C52 C51 176.6(12) . . . . ?
C50 C51 C52 C47 -2.5(19) . . . . ?
N4 C46 C53 C54 -169.6(12) . . . . ?
C47 C46 C53 C54 -48.0(17) . . . . ?
N4 C46 C53 S2 5.7(12) . . . . ?
C47 C46 C53 S2 127.4(10) . . . . ?
C38 S2 C53 C54 171.8(13) . . . . ?
C38 S2 C53 C46 -3.3(10) . . . . ?
C46 C53 C54 C55 -177.5(12) . . . . ?
S2 C53 C54 C55 8(2) . . . . ?
C53 C54 C55 C60 -164.8(15) . . . . ?
C53 C54 C55 C56 13(2) . . . . ?
C60 C55 C56 C57 0(2) . . . . ?
C54 C55 C56 C57 -178.3(15) . . . . ?
C55 C56 C57 C58 -1(2) . . . . ?
C56 C57 C58 C59 0(3) . . . . ?
C57 C58 C59 C60 2(3) . . . . ?
C58 C59 C60 C55 -3(3) . . . . ?
C56 C55 C60 C59 2(2) . . . . ?
C54 C55 C60 C59 -179.6(15) . . . . ?

_refine_diff_density_max         0.855
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.100

