# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_DRB318
_database_code_depnum_ccdc_archive 'CCDC 802497'
_audit_update_record             
;
2010-11-29 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
#TrackingRef '3302_web_deposit_cif_file_0_Dr.SolheAlshahateet_1291025895.cif'

_audit_creation_method           'RAELSPUB and manual entry'
_computing_data_collection       'CAD4 Version 5.0, 1989'
_computing_cell_refinement       'CAD4 Version 5.0, 1989'
_computing_data_reduction        'Local program'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement  'RAELS, (Rae, 1989)'
_computing_molecular_graphics    'ORTEP-II, (Johnson, 1976)'
_computing_publication_material  'Local programs'

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H12 Br4 N2 S,C9 H12'
_chemical_formula_sum            'C31 H24 Br4 N2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         776.2

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   10.592(4)
_cell_length_b                   11.235(5)
_cell_length_c                   13.182(7)
_cell_angle_alpha                93.99(3)
_cell_angle_beta                 102.12(2)
_cell_angle_gamma                108.62(2)
_cell_volume                     1438(1)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10
_cell_measurement_theta_min      10
_cell_measurement_theta_max      11
_cell_measurement_temperature    294
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_size_rad          ?
_exptl_crystal_density_diffrn    1.79
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760.0
_exptl_absorpt_coefficient_mu    5.644
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(DeMeulenaer & Tompa, 1965)'
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_T_max  0.52

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_diffrn_reflns_number            5258
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_theta_max         25
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         1
_diffrn_standards_interval_time  30min
_diffrn_standards_decay_%        0

# REFINEMENT DATA

_refine_special_details          ?
_reflns_number_total             5020
_reflns_number_gt                3339
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.039
_refine_ls_wR_factor_ref         0.044
_refine_ls_abs_structure_Flack   ?
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         3339
_refine_ls_number_parameters     180
_refine_ls_goodness_of_fit_ref   1.28
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0004F²]'
_refine_ls_shift/su_max          0.007
_refine_diff_density_max         0.94
_refine_diff_density_min         -1.05
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_atom_type_scat_source           
'International Tables for X-ray Crystallography, Vol. IV'

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_type_symbol
_atom_site_occupancy
Br1 -0.19602(6) 0.13059(6) 0.13430(5) 0.0559(2) Uani Br 1.0
Br2 0.03619(7) 0.43078(6) -0.14518(5) 0.0573(2) Uani Br 1.0
Br3 0.91194(6) 0.26408(6) 0.45195(5) 0.0575(2) Uani Br 1.0
Br4 0.80424(8) 0.61455(6) 0.71634(6) 0.0798(3) Uani Br 1.0
S1 0.2753(2) -0.1577(1) 0.2667(1) 0.045(2) Uani S 1.0
N1 0.0654(4) 0.0597(4) 0.1613(3) 0.033(1) Uani N 1.0
N2 0.5995(4) 0.1406(4) 0.3976(3) 0.036(2) Uani N 1.0
C1 0.1703(5) -0.0582(5) 0.2710(4) 0.038(2) Uani C 1.0
C2 0.1748(5) 0.0253(4) 0.1857(4) 0.034(1) Uani C 1.0
C3 0.2896(5) 0.0696(4) 0.1418(4) 0.0332(9) Uani C 1.0
C4 0.4151(5) 0.0299(5) 0.1702(4) 0.036(1) Uani C 1.0
C5 0.4298(5) -0.0258(5) 0.2737(4) 0.038(2) Uani C 1.0
C6 0.4664(5) 0.0765(5) 0.3665(4) 0.035(1) Uani C 1.0
C7 0.3656(5) 0.1041(5) 0.4106(4) 0.036(1) Uani C 1.0
C8 0.2159(5) 0.0227(5) 0.3793(4) 0.039(2) Uani C 1.0
C9 0.0615(5) 0.1415(4) 0.0903(4) 0.031(1) Uani C 1.0
C10 -0.0523(5) 0.1839(5) 0.0652(4) 0.036(1) Uani C 1.0
C11 -0.0589(5) 0.2675(5) -0.0030(4) 0.040(2) Uani C 1.0
C12 0.0488(5) 0.3117(5) -0.0522(4) 0.041(2) Uani C 1.0
C13 0.1611(5) 0.2748(5) -0.0332(4) 0.039(2) Uani C 1.0
C14 0.1688(5) 0.1880(4) 0.0401(4) 0.033(1) Uani C 1.0
C15 0.2833(5) 0.1498(5) 0.0683(4) 0.037(2) Uani C 1.0
C16 0.6436(5) 0.2427(5) 0.4736(4) 0.036(1) Uani C 1.0
C17 0.7850(5) 0.3151(5) 0.5088(4) 0.041(2) Uani C 1.0
C18 0.8322(5) 0.4233(5) 0.5794(4) 0.047(2) Uani C 1.0
C19 0.7361(6) 0.4620(5) 0.6204(4) 0.051(2) Uani C 1.0
C20 0.6001(6) 0.3949(5) 0.5933(4) 0.049(2) Uani C 1.0
C21 0.5501(5) 0.2824(5) 0.5192(4) 0.039(1) Uani C 1.0
C22 0.4108(5) 0.2084(5) 0.4846(4) 0.041(1) Uani C 1.0
C1M 0.7153(3) 0.7681(3) 0.2709(2) 0.047(1) Uani C 1.0
C2M 0.7307(3) 0.6549(3) 0.2958(2) 0.055(2) Uani C 1.0
C3M 0.6354(3) 0.5402(3) 0.2422(2) 0.057(2) Uani C 1.0
C4M 0.5248(3) 0.5389(3) 0.1637(2) 0.049(2) Uani C 1.0
C5M 0.5094(3) 0.6521(3) 0.1388(2) 0.047(1) Uani C 1.0
C6M 0.6047(3) 0.7668(3) 0.1924(2) 0.048(1) Uani C 1.0
C7M 0.8202(4) 0.8944(4) 0.3300(3) 0.067(2) Uani C 1.0
C8M 0.6523(5) 0.4155(4) 0.2696(4) 0.098(3) Uani C 1.0
C9M 0.3876(4) 0.6506(4) 0.0524(4) 0.074(2) Uani C 1.0
HC1 0.0729 -0.1151 0.2611 0.044 Uani H 1.0
H1C4 0.4987 0.1063 0.1767 0.037 Uani H 1.0
H2C4 0.4093 -0.0356 0.1124 0.043 Uani H 1.0
HC5 0.5074 -0.0596 0.2802 0.044 Uani H 1.0
H1C8 0.1601 0.0796 0.3791 0.041 Uani H 1.0
H2C8 0.1976 -0.0355 0.4326 0.046 Uani H 1.0
HC11 -0.1394 0.2973 -0.0181 0.047 Uani H 1.0
HC13 0.2363 0.3076 -0.0697 0.047 Uani H 1.0
HC15 0.3616 0.1813 0.0346 0.046 Uani H 1.0
HC18 0.9325 0.4742 0.6018 0.053 Uani H 1.0
HC20 0.5353 0.4242 0.6251 0.059 Uani H 1.0
HC22 0.3425 0.2332 0.5153 0.050 Uani H 1.0
HC2M 0.8105 0.6559 0.3525 0.076 Uani H 1.0
HC4M 0.4560 0.4561 0.1250 0.062 Uani H 1.0
HC6M 0.5936 0.8485 0.1745 0.064 Uani H 1.0
H1C7M 0.8774 0.8791 0.3950 0.079 Uani H 1.0
H2C7M 0.8809 0.9350 0.2842 0.075 Uani H 1.0
H3C7M 0.7711 0.9518 0.3495 0.077 Uani H 1.0
H1C8M 0.5672 0.3431 0.2331 0.107 Uani H 1.0
H2C8M 0.7328 0.4055 0.2464 0.112 Uani H 1.0
H3C8M 0.6679 0.4163 0.3472 0.121 Uani H 1.0
H1C9M 0.4048 0.7371 0.0315 0.091 Uani H 1.0
H2C9M 0.3758 0.5881 -0.0098 0.079 Uani H 1.0
H3C9M 0.3023 0.6254 0.0788 0.090 Uani H 1.0

# MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.893(5) 1_555 1_555 no
Br2 C12 1.893(5) 1_555 1_555 no
Br3 C17 1.885(6) 1_555 1_555 no
Br4 C19 1.893(5) 1_555 1_555 no
S1 C1 1.817(5) 1_555 1_555 no
S1 C5 1.803(5) 1_555 1_555 no
N1 C2 1.320(6) 1_555 1_555 no
N1 C9 1.359(6) 1_555 1_555 no
N2 C6 1.320(6) 1_555 1_555 no
N2 C16 1.356(6) 1_555 1_555 no
C1 C2 1.513(7) 1_555 1_555 no
C1 C8 1.532(7) 1_555 1_555 no
C2 C3 1.418(7) 1_555 1_555 no
C3 C4 1.516(7) 1_555 1_555 no
C3 C15 1.373(7) 1_555 1_555 no
C4 C5 1.539(7) 1_555 1_555 no
C5 C6 1.514(7) 1_555 1_555 no
C6 C7 1.421(7) 1_555 1_555 no
C7 C8 1.506(7) 1_555 1_555 no
C7 C22 1.357(7) 1_555 1_555 no
C9 C10 1.418(7) 1_555 1_555 no
C9 C14 1.409(7) 1_555 1_555 no
C10 C11 1.352(7) 1_555 1_555 no
C11 C12 1.401(7) 1_555 1_555 no
C12 C13 1.361(7) 1_555 1_555 no
C13 C14 1.429(7) 1_555 1_555 no
C14 C15 1.400(7) 1_555 1_555 no
C16 C17 1.414(7) 1_555 1_555 no
C16 C21 1.427(7) 1_555 1_555 no
C17 C18 1.361(7) 1_555 1_555 no
C18 C19 1.413(8) 1_555 1_555 no
C19 C20 1.350(7) 1_555 1_555 no
C20 C21 1.421(7) 1_555 1_555 no
C21 C22 1.398(7) 1_555 1_555 no
C1M C2M 1.386(2) 1_555 1_555 no
C1M C6M 1.386(2) 1_555 1_555 no
C1M C7M 1.526(4) 1_555 1_555 no
C2M C3M 1.386(2) 1_555 1_555 no
C3M C4M 1.386(2) 1_555 1_555 no
C3M C8M 1.526(4) 1_555 1_555 no
C4M C5M 1.386(2) 1_555 1_555 no
C5M C6M 1.386(2) 1_555 1_555 no
C5M C9M 1.526(4) 1_555 1_555 no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C5 94.0(2) 1_555 1_555 1_555 no
C2 N1 C9 118.8(4) 1_555 1_555 1_555 no
C6 N2 C16 118.4(4) 1_555 1_555 1_555 no
S1 C1 C2 112.9(4) 1_555 1_555 1_555 no
S1 C1 C8 109.3(4) 1_555 1_555 1_555 no
C2 C1 C8 110.4(4) 1_555 1_555 1_555 no
N1 C2 C1 113.3(4) 1_555 1_555 1_555 no
N1 C2 C3 123.3(5) 1_555 1_555 1_555 no
C1 C2 C3 123.2(5) 1_555 1_555 1_555 no
C2 C3 C4 123.1(5) 1_555 1_555 1_555 no
C2 C3 C15 117.4(5) 1_555 1_555 1_555 no
C4 C3 C15 119.4(5) 1_555 1_555 1_555 no
C3 C4 C5 114.1(4) 1_555 1_555 1_555 no
S1 C5 C4 109.0(3) 1_555 1_555 1_555 no
S1 C5 C6 113.9(4) 1_555 1_555 1_555 no
C4 C5 C6 110.7(4) 1_555 1_555 1_555 no
N2 C6 C5 113.0(4) 1_555 1_555 1_555 no
N2 C6 C7 124.2(4) 1_555 1_555 1_555 no
C5 C6 C7 122.7(4) 1_555 1_555 1_555 no
C6 C7 C8 122.8(4) 1_555 1_555 1_555 no
C6 C7 C22 116.6(5) 1_555 1_555 1_555 no
C8 C7 C22 120.6(5) 1_555 1_555 1_555 no
C1 C8 C7 114.4(4) 1_555 1_555 1_555 no
N1 C9 C10 120.2(5) 1_555 1_555 1_555 no
N1 C9 C14 122.2(4) 1_555 1_555 1_555 no
C10 C9 C14 117.7(5) 1_555 1_555 1_555 no
Br1 C10 C9 119.7(4) 1_555 1_555 1_555 no
Br1 C10 C11 118.0(4) 1_555 1_555 1_555 no
C9 C10 C11 122.2(5) 1_555 1_555 1_555 no
C10 C11 C12 119.0(5) 1_555 1_555 1_555 no
Br2 C12 C11 117.3(4) 1_555 1_555 1_555 no
Br2 C12 C13 120.1(4) 1_555 1_555 1_555 no
C11 C12 C13 122.6(5) 1_555 1_555 1_555 no
C12 C13 C14 118.3(5) 1_555 1_555 1_555 no
C9 C14 C13 120.3(5) 1_555 1_555 1_555 no
C9 C14 C15 117.4(5) 1_555 1_555 1_555 no
C13 C14 C15 122.3(5) 1_555 1_555 1_555 no
C3 C15 C14 120.8(5) 1_555 1_555 1_555 no
N2 C16 C17 120.5(5) 1_555 1_555 1_555 no
N2 C16 C21 121.7(4) 1_555 1_555 1_555 no
C17 C16 C21 117.7(4) 1_555 1_555 1_555 no
Br3 C17 C16 118.9(4) 1_555 1_555 1_555 no
Br3 C17 C18 118.8(4) 1_555 1_555 1_555 no
C16 C17 C18 122.2(5) 1_555 1_555 1_555 no
C17 C18 C19 118.5(5) 1_555 1_555 1_555 no
Br4 C19 C18 117.5(4) 1_555 1_555 1_555 no
Br4 C19 C20 119.9(5) 1_555 1_555 1_555 no
C18 C19 C20 122.6(5) 1_555 1_555 1_555 no
C19 C20 C21 119.3(5) 1_555 1_555 1_555 no
C16 C21 C20 119.7(5) 1_555 1_555 1_555 no
C16 C21 C22 116.9(4) 1_555 1_555 1_555 no
C20 C21 C22 123.3(5) 1_555 1_555 1_555 no
C7 C22 C21 122.0(5) 1_555 1_555 1_555 no
C2M C1M C6M 120.0 1_555 1_555 1_555 no
C2M C1M C7M 120.0 1_555 1_555 1_555 no
C6M C1M C7M 120.0 1_555 1_555 1_555 no
C1M C2M C3M 120.0 1_555 1_555 1_555 no
C2M C3M C4M 120.0 1_555 1_555 1_555 no
C2M C3M C8M 120.0 1_555 1_555 1_555 no
C4M C3M C8M 120.0 1_555 1_555 1_555 no
C3M C4M C5M 120.0 1_555 1_555 1_555 no
C4M C5M C6M 120.0 1_555 1_555 1_555 no
C4M C5M C9M 120.0 1_555 1_555 1_555 no
C6M C5M C9M 120.0 1_555 1_555 1_555 no
C1M C6M C5M 120.0 1_555 1_555 1_555 no


####################################################################### 
# 
# 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_4284
_database_code_depnum_ccdc_archive 'CCDC 1419533'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2015-10-27 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 H15.50 Br4 N2.50 S'
_chemical_formula_weight         702.60

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1820(18)
_cell_length_b                   9.6642(19)
_cell_length_c                   14.466(3)
_cell_angle_alpha                83.296(4)
_cell_angle_beta                 75.723(4)
_cell_angle_gamma                73.399(4)
_cell_volume                     1190.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    853
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      24.76

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             678
_exptl_absorpt_coefficient_mu    6.866
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_absorpt_correction_T_min  0.2325
_exptl_absorpt_correction_T_max  0.5468
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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            15602
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5464
_reflns_number_gt                4096
_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)+(0.0450P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5464
_refine_ls_number_parameters     313
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.030
_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 -0.28204(6) 0.29551(5) 0.89124(3) 0.04351(14) Uani 1 1 d . . .
Br2 Br -0.32275(5) 0.82495(5) 1.03672(3) 0.03674(13) Uani 1 1 d . . .
Br3 Br 0.19161(7) 1.08118(7) 0.24637(3) 0.06337(19) Uani 1 1 d . . .
Br4 Br 0.65982(7) 0.67912(6) 0.40107(3) 0.05828(17) Uani 1 1 d . . .
S1 S 0.42114(12) 0.86038(12) 0.85812(7) 0.0337(2) Uani 1 1 d . . .
N1 N 0.0139(4) 0.7713(3) 0.9165(2) 0.0287(7) Uani 1 1 d . . .
N2 N 0.4610(4) 0.8086(3) 0.5854(2) 0.0316(7) Uani 1 1 d . . .
C1 C 0.1940(5) 0.5275(4) 0.8166(3) 0.0313(9) Uani 1 1 d . . .
H1 H 0.2552 0.4452 0.7832 0.038 Uiso 1 1 calc R . .
C2 C 0.0379(5) 0.5359(4) 0.8619(3) 0.0284(8) Uani 1 1 d . . .
C3 C -0.0336(5) 0.4267(4) 0.8550(3) 0.0326(9) Uani 1 1 d . . .
H3 H 0.0232 0.3450 0.8197 0.039 Uiso 1 1 calc R . .
C4 C -0.1848(5) 0.4416(4) 0.8999(3) 0.0317(9) Uani 1 1 d . . .
C5 C -0.2731(5) 0.5601(4) 0.9542(3) 0.0315(9) Uani 1 1 d . . .
H5 H -0.3774 0.5667 0.9855 0.038 Uiso 1 1 calc R . .
C6 C -0.2053(5) 0.6670(4) 0.9612(3) 0.0288(8) Uani 1 1 d . . .
C7 C -0.0483(5) 0.6596(4) 0.9137(3) 0.0273(8) Uani 1 1 d . . .
C8 C 0.1600(5) 0.7604(4) 0.8713(3) 0.0272(8) Uani 1 1 d . . .
C9 C 0.2124(5) 0.8961(4) 0.8724(3) 0.0291(8) Uani 1 1 d . . .
H9 H 0.1608 0.9402 0.9346 0.035 Uiso 1 1 calc R . .
C10 C 0.1634(5) 1.0066(4) 0.7932(3) 0.0315(9) Uani 1 1 d . . .
H10A H 0.0505 1.0268 0.8006 0.038 Uiso 1 1 calc R . .
H10B H 0.1860 1.0970 0.8015 0.038 Uiso 1 1 calc R . .
C11 C 0.2431(5) 0.9589(4) 0.6932(3) 0.0292(8) Uani 1 1 d . . .
C12 C 0.1794(5) 1.0216(5) 0.6169(3) 0.0361(9) Uani 1 1 d . . .
H12 H 0.0840 1.0934 0.6277 0.043 Uiso 1 1 calc R . .
C13 C 0.2530(5) 0.9813(5) 0.5240(3) 0.0371(10) Uani 1 1 d . . .
C14 C 0.1923(6) 1.0439(5) 0.4429(3) 0.0453(11) Uani 1 1 d . . .
H14 H 0.0981 1.1173 0.4500 0.054 Uiso 1 1 calc R . .
C15 C 0.2716(6) 0.9967(6) 0.3550(3) 0.0465(12) Uani 1 1 d . . .
C16 C 0.4124(6) 0.8889(5) 0.3401(3) 0.0451(12) Uani 1 1 d . . .
H16 H 0.4655 0.8592 0.2783 0.054 Uiso 1 1 calc R . .
C17 C 0.4706(6) 0.8278(5) 0.4179(3) 0.0427(11) Uani 1 1 d . . .
C18 C 0.3949(5) 0.8724(4) 0.5111(3) 0.0348(9) Uani 1 1 d . . .
C19 C 0.3874(5) 0.8518(4) 0.6723(3) 0.0286(8) Uani 1 1 d . . .
C20 C 0.4677(5) 0.7672(4) 0.7487(3) 0.0301(8) Uani 1 1 d . . .
H20 H 0.5817 0.7467 0.7229 0.036 Uiso 1 1 calc R . .
C21 C 0.4268(5) 0.6228(4) 0.7726(3) 0.0331(9) Uani 1 1 d . . .
H21A H 0.4515 0.5721 0.7136 0.040 Uiso 1 1 calc R . .
H21B H 0.4920 0.5633 0.8147 0.040 Uiso 1 1 calc R . .
C22 C 0.2581(4) 0.6376(4) 0.8205(2) 0.0283(8) Uani 1 1 d . . .
C7S C 0.1749(18) 0.5770(18) 0.393(2) 0.108(9) Uani 0.50 1 d PD A -1
H7SA H 0.2101 0.6341 0.4297 0.162 Uiso 0.50 1 calc PR A -1
H7SB H 0.1341 0.6374 0.3420 0.162 Uiso 0.50 1 calc PR A -1
H7SC H 0.2617 0.4977 0.3665 0.162 Uiso 0.50 1 calc PR A -1
C6S C 0.0563(12) 0.5213(12) 0.4539(7) 0.074(4) Uani 0.50 1 d PGDU A -1
N1S N 0.0044(13) 0.5628(11) 0.5478(8) 0.079(4) Uani 0.50 1 d PGDU A -1
C2S C -0.1121(13) 0.5104(14) 0.6096(7) 0.118(7) Uani 0.50 1 d PGDU A -1
H2S H -0.1472 0.5385 0.6731 0.141 Uiso 0.50 1 calc PR A -1
C3S C -0.1768(13) 0.4166(14) 0.5775(13) 0.142(15) Uani 0.50 1 d PGDU A -1
H3S H -0.2556 0.3812 0.6193 0.171 Uiso 0.50 1 calc PR A -1
C4S C -0.1249(18) 0.3751(12) 0.4836(14) 0.133(7) Uani 0.50 1 d PGDU A -1
H4S H -0.1686 0.3117 0.4619 0.160 Uiso 0.50 1 calc PR A -1
C5S C -0.0083(18) 0.4275(14) 0.4218(9) 0.123(9) Uani 0.50 1 d PGDU A -1
H5S H 0.0268 0.3994 0.3583 0.147 Uiso 0.50 1 calc PR A -1


_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 C4 1.903(4) . ?
Br2 C6 1.885(4) . ?
Br3 C15 1.898(4) . ?
Br4 C17 1.895(5) . ?
S1 C9 1.810(4) . ?
S1 C20 1.811(4) . ?
N1 C8 1.320(5) . ?
N1 C7 1.366(5) . ?
N2 C19 1.324(5) . ?
N2 C18 1.362(5) . ?
C1 C22 1.367(5) . ?
C1 C2 1.405(6) . ?
C2 C7 1.412(5) . ?
C2 C3 1.417(5) . ?
C3 C4 1.354(6) . ?
C4 C5 1.397(5) . ?
C5 C6 1.374(5) . ?
C6 C7 1.421(5) . ?
C8 C22 1.422(5) . ?
C8 C9 1.524(5) . ?
C9 C10 1.532(5) . ?
C10 C11 1.510(5) . ?
C11 C12 1.374(5) . ?
C11 C19 1.418(5) . ?
C12 C13 1.393(6) . ?
C13 C18 1.408(6) . ?
C13 C14 1.420(6) . ?
C14 C15 1.357(7) . ?
C15 C16 1.396(7) . ?
C16 C17 1.363(6) . ?
C17 C18 1.411(6) . ?
C19 C20 1.511(5) . ?
C20 C21 1.526(6) . ?
C21 C22 1.506(5) . ?
C7S C6S 1.413(17) . ?
C6S N1S 1.3900 . ?
C6S C5S 1.3900 . ?
N1S C2S 1.3900 . ?
C2S C3S 1.3900 . ?
C3S C4S 1.3900 . ?
C4S C5S 1.3900 . ?

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
C9 S1 C20 94.15(18) . . ?
C8 N1 C7 118.5(3) . . ?
C19 N2 C18 117.9(3) . . ?
C22 C1 C2 120.9(3) . . ?
C1 C2 C7 117.6(3) . . ?
C1 C2 C3 122.0(3) . . ?
C7 C2 C3 120.4(4) . . ?
C4 C3 C2 119.1(4) . . ?
C3 C4 C5 122.4(4) . . ?
C3 C4 Br1 119.5(3) . . ?
C5 C4 Br1 118.1(3) . . ?
C6 C5 C4 119.0(4) . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 Br2 119.1(3) . . ?
C7 C6 Br2 119.6(3) . . ?
N1 C7 C2 121.9(4) . . ?
N1 C7 C6 120.4(3) . . ?
C2 C7 C6 117.7(3) . . ?
N1 C8 C22 123.7(3) . . ?
N1 C8 C9 113.8(3) . . ?
C22 C8 C9 122.3(3) . . ?
C8 C9 C10 110.9(3) . . ?
C8 C9 S1 113.2(3) . . ?
C10 C9 S1 108.1(3) . . ?
C11 C10 C9 114.3(3) . . ?
C12 C11 C19 116.5(4) . . ?
C12 C11 C10 120.7(4) . . ?
C19 C11 C10 122.7(3) . . ?
C11 C12 C13 121.5(4) . . ?
C12 C13 C18 117.4(4) . . ?
C12 C13 C14 123.5(4) . . ?
C18 C13 C14 119.1(4) . . ?
C15 C14 C13 119.3(5) . . ?
C14 C15 C16 122.8(4) . . ?
C14 C15 Br3 119.4(4) . . ?
C16 C15 Br3 117.7(3) . . ?
C17 C16 C15 118.0(4) . . ?
C16 C17 C18 122.1(5) . . ?
C16 C17 Br4 119.4(4) . . ?
C18 C17 Br4 118.4(3) . . ?
N2 C18 C13 122.4(4) . . ?
N2 C18 C17 119.1(4) . . ?
C13 C18 C17 118.6(4) . . ?
N2 C19 C11 124.3(4) . . ?
N2 C19 C20 112.8(3) . . ?
C11 C19 C20 122.8(3) . . ?
C19 C20 C21 110.0(3) . . ?
C19 C20 S1 114.3(3) . . ?
C21 C20 S1 108.6(3) . . ?
C22 C21 C20 113.6(3) . . ?
C1 C22 C8 117.3(4) . . ?
C1 C22 C21 119.1(3) . . ?
C8 C22 C21 123.6(3) . . ?
N1S C6S C5S 120.0 . . ?
N1S C6S C7S 118.3(15) . . ?
C5S C6S C7S 121.7(15) . . ?
C6S N1S C2S 120.0 . . ?
C3S C2S N1S 120.0 . . ?
C4S C3S C2S 120.0 . . ?
C5S C4S C3S 120.0 . . ?
C4S C5S C6S 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.568
_refine_diff_density_min         -1.284
_refine_diff_density_rms         0.119
####################################################################### 
# 
# 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_4206
_database_code_depnum_ccdc_archive 'CCDC 1419534'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2015-10-27 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 H15.50 Br4 N2.50 S'
_chemical_formula_weight         702.60

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1907(13)
_cell_length_b                   9.4970(15)
_cell_length_c                   15.261(2)
_cell_angle_alpha                90.457(3)
_cell_angle_beta                 96.073(4)
_cell_angle_gamma                98.192(3)
_cell_volume                     1168.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1002
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.998
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             678
_exptl_absorpt_coefficient_mu    6.999
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_absorpt_correction_T_min  0.1276
_exptl_absorpt_correction_T_max  0.3350
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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            15315
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5360
_reflns_number_gt                4040
_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)+(0.0575P)²+0.8692P] 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         5360
_refine_ls_number_parameters     313
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.77156(6) 0.93602(6) 0.92533(3) 0.06398(16) Uani 1 1 d . . .
Br2 Br 0.14611(5) 0.65985(5) 0.99568(3) 0.05135(14) Uani 1 1 d . . .
Br3 Br -0.07036(8) 0.37623(6) 0.25962(3) 0.07573(19) Uani 1 1 d . . .
Br4 Br 0.35428(6) 0.00581(5) 0.40384(3) 0.05883(15) Uani 1 1 d . . .
S1 S 0.18192(16) 0.00635(11) 0.82513(7) 0.0535(3) Uani 1 1 d . . .
N1 N 0.2500(4) 0.4134(3) 0.8935(2) 0.0378(7) Uani 1 1 d . . .
N2 N 0.2350(4) 0.0943(3) 0.5778(2) 0.0398(7) Uani 1 1 d . . .
C1 C 0.5470(5) 0.4010(5) 0.8228(3) 0.0477(10) Uani 1 1 d . . .
H1 H 0.6469 0.3955 0.8000 0.057 Uiso 1 1 calc R . .
C2 C 0.5261(5) 0.5276(5) 0.8676(2) 0.0417(9) Uani 1 1 d . . .
C3 C 0.6474(5) 0.6495(5) 0.8761(3) 0.0481(10) Uani 1 1 d . . .
H3 H 0.7488 0.6486 0.8540 0.058 Uiso 1 1 calc R . .
C4 C 0.6146(5) 0.7673(5) 0.9168(3) 0.0452(9) Uani 1 1 d . . .
C5 C 0.4635(5) 0.7722(4) 0.9531(3) 0.0454(9) Uani 1 1 d . . .
H5 H 0.4443 0.8545 0.9812 0.054 Uiso 1 1 calc R . .
C6 C 0.3472(5) 0.6546(4) 0.9462(2) 0.0395(8) Uani 1 1 d . . .
C7 C 0.3710(5) 0.5273(4) 0.9023(2) 0.0377(8) Uani 1 1 d . . .
C8 C 0.2756(5) 0.2991(4) 0.8503(2) 0.0393(8) Uani 1 1 d . . .
C9 C 0.1275(5) 0.1832(4) 0.8395(2) 0.0419(9) Uani 1 1 d . . .
H9 H 0.0716 0.1836 0.8931 0.050 Uiso 1 1 calc R . .
C10 C 0.0038(5) 0.2126(4) 0.7622(3) 0.0424(9) Uani 1 1 d . . .
H10A H -0.0971 0.1457 0.7632 0.051 Uiso 1 1 calc R . .
H10B H -0.0241 0.3075 0.7700 0.051 Uiso 1 1 calc R . .
C11 C 0.0666(5) 0.2017(4) 0.6730(2) 0.0388(8) Uani 1 1 d . . .
C12 C -0.0024(5) 0.2690(4) 0.6022(3) 0.0442(9) Uani 1 1 d . . .
H12 H -0.0797 0.3293 0.6107 0.053 Uiso 1 1 calc R . .
C13 C 0.0419(5) 0.2483(4) 0.5169(3) 0.0409(8) Uani 1 1 d . . .
C14 C -0.0262(5) 0.3163(4) 0.4418(3) 0.0486(10) Uani 1 1 d . . .
H14 H -0.0997 0.3809 0.4479 0.058 Uiso 1 1 calc R . .
C15 C 0.0168(6) 0.2864(5) 0.3613(3) 0.0502(10) Uani 1 1 d . . .
C16 C 0.1281(5) 0.1901(5) 0.3491(3) 0.0493(10) Uani 1 1 d . . .
H16 H 0.1540 0.1695 0.2930 0.059 Uiso 1 1 calc R . .
C17 C 0.1968(5) 0.1278(4) 0.4207(3) 0.0426(9) Uani 1 1 d . . .
C18 C 0.1592(5) 0.1549(4) 0.5074(2) 0.0388(8) Uani 1 1 d . . .
C19 C 0.1921(5) 0.1175(4) 0.6569(2) 0.0386(8) Uani 1 1 d . . .
C20 C 0.2938(5) 0.0547(4) 0.7307(2) 0.0443(9) Uani 1 1 d . . .
H20 H 0.3271 -0.0321 0.7075 0.053 Uiso 1 1 calc R . .
C21 C 0.4526(5) 0.1562(5) 0.7625(3) 0.0479(10) Uani 1 1 d . . .
H21A H 0.5250 0.1044 0.8002 0.057 Uiso 1 1 calc R . .
H21B H 0.5096 0.1859 0.7116 0.057 Uiso 1 1 calc R . .
C22 C 0.4251(5) 0.2882(4) 0.8126(2) 0.0412(9) Uani 1 1 d . . .
C1S C 0.5058(17) 0.4495(14) 0.3910(5) 0.116(8) Uani 0.50 1 d PG A -1
H1SA H 0.5154 0.4123 0.3356 0.139 Uiso 0.50 1 calc PR A -1
C2S C 0.5482(16) 0.3749(11) 0.4660(8) 0.128(9) Uani 0.50 1 d PG A -1
H2SA H 0.5861 0.2878 0.4608 0.154 Uiso 0.50 1 calc PR A -1
C3S C 0.5338(15) 0.4304(12) 0.5490(6) 0.102(7) Uani 0.50 1 d PGD A -1
H3SA H 0.5621 0.3804 0.5992 0.122 Uiso 0.50 1 calc PR A -1
C4S C 0.4770(14) 0.5605(12) 0.5569(5) 0.070(4) Uani 0.50 1 d PG A -1
C5S C 0.4346(13) 0.6352(10) 0.4819(7) 0.086(5) Uani 0.50 1 d PGD A -1
H5SA H 0.3966 0.7223 0.4872 0.103 Uiso 0.50 1 calc PR A -1
N6S N 0.4490(15) 0.5796(13) 0.3990(5) 0.108(5) Uani 0.50 1 d PG A -1
C7S C 0.455(3) 0.617(2) 0.6443(10) 0.135(8) Uani 0.50 1 d PD A -1
H7SA H 0.4157 0.7072 0.6381 0.202 Uiso 0.50 1 calc PR A -1
H7SB H 0.5592 0.6286 0.6807 0.202 Uiso 0.50 1 calc PR A -1
H7SC H 0.3756 0.5515 0.6712 0.202 Uiso 0.50 1 calc PR A -1


_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 C4 1.900(4) . ?
Br2 C6 1.890(4) . ?
Br3 C15 1.898(4) . ?
Br4 C17 1.888(4) . ?
S1 C9 1.815(4) . ?
S1 C20 1.816(4) . ?
N1 C8 1.319(5) . ?
N1 C7 1.355(5) . ?
N2 C19 1.317(5) . ?
N2 C18 1.358(5) . ?
C1 C22 1.353(6) . ?
C1 C2 1.418(6) . ?
C2 C3 1.410(6) . ?
C2 C7 1.427(5) . ?
C3 C4 1.349(6) . ?
C4 C5 1.415(6) . ?
C5 C6 1.356(6) . ?
C6 C7 1.424(5) . ?
C8 C22 1.423(5) . ?
C8 C9 1.512(6) . ?
C9 C10 1.525(6) . ?
C10 C11 1.514(5) . ?
C11 C12 1.371(6) . ?
C11 C19 1.429(5) . ?
C12 C13 1.408(5) . ?
C13 C18 1.415(5) . ?
C13 C14 1.422(6) . ?
C14 C15 1.352(6) . ?
C15 C16 1.404(6) . ?
C16 C17 1.355(6) . ?
C17 C18 1.420(5) . ?
C19 C20 1.507(5) . ?
C20 C21 1.535(6) . ?
C21 C22 1.519(5) . ?
C1S C2S 1.3900 . ?
C1S N6S 1.3900 . ?
C2S C3S 1.3900 . ?
C3S C4S 1.3900 . ?
C4S C5S 1.3900 . ?
C4S C7S 1.472(18) . ?
C5S N6S 1.3900 . ?

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
C9 S1 C20 93.71(18) . . ?
C8 N1 C7 118.8(3) . . ?
C19 N2 C18 119.0(3) . . ?
C22 C1 C2 121.5(4) . . ?
C3 C2 C1 123.0(4) . . ?
C3 C2 C7 120.8(4) . . ?
C1 C2 C7 116.1(4) . . ?
C4 C3 C2 119.2(4) . . ?
C3 C4 C5 122.3(4) . . ?
C3 C4 Br1 120.4(3) . . ?
C5 C4 Br1 117.4(3) . . ?
C6 C5 C4 118.9(4) . . ?
C5 C6 C7 122.2(4) . . ?
C5 C6 Br2 119.0(3) . . ?
C7 C6 Br2 118.8(3) . . ?
N1 C7 C6 120.9(3) . . ?
N1 C7 C2 122.4(3) . . ?
C6 C7 C2 116.7(4) . . ?
N1 C8 C22 123.4(4) . . ?
N1 C8 C9 113.8(3) . . ?
C22 C8 C9 122.6(3) . . ?
C8 C9 C10 111.0(3) . . ?
C8 C9 S1 113.6(3) . . ?
C10 C9 S1 109.1(3) . . ?
C11 C10 C9 114.0(3) . . ?
C12 C11 C19 116.9(3) . . ?
C12 C11 C10 120.1(3) . . ?
C19 C11 C10 122.9(3) . . ?
C11 C12 C13 121.1(4) . . ?
C12 C13 C18 117.3(4) . . ?
C12 C13 C14 122.9(4) . . ?
C18 C13 C14 119.8(4) . . ?
C15 C14 C13 119.6(4) . . ?
C14 C15 C16 122.0(4) . . ?
C14 C15 Br3 120.7(3) . . ?
C16 C15 Br3 117.3(3) . . ?
C17 C16 C15 118.7(4) . . ?
C16 C17 C18 122.5(4) . . ?
C16 C17 Br4 118.2(3) . . ?
C18 C17 Br4 119.2(3) . . ?
N2 C18 C13 121.9(3) . . ?
N2 C18 C17 120.8(3) . . ?
C13 C18 C17 117.3(3) . . ?
N2 C19 C11 123.5(3) . . ?
N2 C19 C20 114.3(3) . . ?
C11 C19 C20 122.1(3) . . ?
C19 C20 C21 111.5(3) . . ?
C19 C20 S1 113.8(3) . . ?
C21 C20 S1 108.5(3) . . ?
C22 C21 C20 114.9(3) . . ?
C1 C22 C8 117.7(3) . . ?
C1 C22 C21 119.4(3) . . ?
C8 C22 C21 122.9(4) . . ?
C2S C1S N6S 120.0 . . ?
C1S C2S C3S 120.0 . . ?
C4S C3S C2S 120.0 . . ?
C3S C4S C5S 120.0 . . ?
C3S C4S C7S 120.2(4) . . ?
C5S C4S C7S 119.8(4) . . ?
C4S C5S N6S 120.0 . . ?
C5S N6S C1S 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.719
_refine_diff_density_min         -1.503
_refine_diff_density_rms         0.094
####################################################################### 
# 
# 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_4205_solhe1G
_database_code_depnum_ccdc_archive 'CCDC 1419535'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2015-10-27 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 H15.50 Br4 N2.50 S'
_chemical_formula_weight         702.60

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7119(10)
_cell_length_b                   10.6252(15)
_cell_length_c                   15.117(2)
_cell_angle_alpha                98.268(3)
_cell_angle_beta                 99.550(3)
_cell_angle_gamma                101.403(3)
_cell_volume                     1177.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    909
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      21.72

_exptl_crystal_description       Block
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             678
_exptl_absorpt_coefficient_mu    6.945
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_absorpt_correction_T_min  0.1677
_exptl_absorpt_correction_T_max  0.3372
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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            15434
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5401
_reflns_number_gt                3667
_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)+(0.0751P)²+0.4009P] 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         5401
_refine_ls_number_parameters     313
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1312
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.76159(8) 0.95207(6) 0.91588(5) 0.0641(2) Uani 1 1 d . . .
Br2 Br 0.12630(7) 0.65920(5) 0.98971(4) 0.04775(17) Uani 1 1 d . . .
Br3 Br -0.16331(14) 0.29500(10) 0.26908(5) 0.1039(3) Uani 1 1 d . . .
Br4 Br 0.40553(8) 0.07629(7) 0.41079(4) 0.0631(2) Uani 1 1 d . . .
S1 S 0.22278(18) 0.04833(13) 0.83407(9) 0.0446(3) Uani 1 1 d . . .
N1 N 0.2626(5) 0.4293(4) 0.9012(2) 0.0351(8) Uani 1 1 d . . .
N2 N 0.2487(5) 0.1133(4) 0.5841(3) 0.0380(9) Uani 1 1 d . . .
C1 C 0.5789(6) 0.4373(5) 0.8344(3) 0.0421(12) Uani 1 1 d . . .
H1 H 0.6857 0.4391 0.8131 0.051 Uiso 1 1 calc R . .
C2 C 0.5446(6) 0.5537(5) 0.8747(3) 0.0367(11) Uani 1 1 d . . .
C3 C 0.6598(6) 0.6767(5) 0.8784(3) 0.0417(11) Uani 1 1 d . . .
H3 H 0.7669 0.6820 0.8572 0.050 Uiso 1 1 calc R . .
C4 C 0.6123(7) 0.7865(5) 0.9133(3) 0.0417(11) Uani 1 1 d . . .
C5 C 0.4532(6) 0.7831(5) 0.9474(3) 0.0411(11) Uani 1 1 d . . .
H5 H 0.4241 0.8599 0.9717 0.049 Uiso 1 1 calc R . .
C6 C 0.3414(6) 0.6635(5) 0.9441(3) 0.0372(11) Uani 1 1 d . . .
C7 C 0.3800(6) 0.5456(5) 0.9066(3) 0.0337(10) Uani 1 1 d . . .
C8 C 0.3002(6) 0.3221(5) 0.8616(3) 0.0356(10) Uani 1 1 d . . .
C9 C 0.1506(6) 0.1993(5) 0.8515(3) 0.0379(11) Uani 1 1 d . . .
H9 H 0.1028 0.2044 0.9078 0.046 Uiso 1 1 calc R . .
C10 C -0.0025(6) 0.1964(5) 0.7735(3) 0.0419(11) Uani 1 1 d . . .
H10A H -0.1029 0.1251 0.7733 0.050 Uiso 1 1 calc R . .
H10B H -0.0432 0.2771 0.7835 0.050 Uiso 1 1 calc R . .
C11 C 0.0502(6) 0.1800(5) 0.6810(3) 0.0385(11) Uani 1 1 d . . .
C12 C -0.0491(7) 0.2162(5) 0.6078(4) 0.0479(13) Uani 1 1 d . . .
H12 H -0.1481 0.2511 0.6159 0.057 Uiso 1 1 calc R . .
C13 C -0.0029(7) 0.2013(5) 0.5223(4) 0.0475(13) Uani 1 1 d . . .
C14 C -0.0991(8) 0.2420(6) 0.4476(4) 0.0582(15) Uani 1 1 d . . .
H14 H -0.2014 0.2740 0.4531 0.070 Uiso 1 1 calc R . .
C15 C -0.0404(9) 0.2338(6) 0.3682(4) 0.0626(17) Uani 1 1 d . . .
C16 C 0.1100(8) 0.1845(6) 0.3562(4) 0.0565(15) Uani 1 1 d . . .
H16 H 0.1467 0.1796 0.3005 0.068 Uiso 1 1 calc R . .
C17 C 0.2023(7) 0.1437(5) 0.4267(3) 0.0453(12) Uani 1 1 d . . .
C18 C 0.1510(7) 0.1512(5) 0.5142(3) 0.0412(11) Uani 1 1 d . . .
C19 C 0.1998(6) 0.1265(5) 0.6645(3) 0.0385(11) Uani 1 1 d . . .
C20 C 0.3250(6) 0.0891(5) 0.7387(3) 0.0400(11) Uani 1 1 d . . .
H20 H 0.3620 0.0116 0.7117 0.048 Uiso 1 1 calc R . .
C21 C 0.4947(6) 0.1963(5) 0.7758(3) 0.0397(11) Uani 1 1 d . . .
H21A H 0.5784 0.1642 0.8173 0.048 Uiso 1 1 calc R . .
H21B H 0.5520 0.2172 0.7256 0.048 Uiso 1 1 calc R . .
C22 C 0.4581(6) 0.3193(5) 0.8253(3) 0.0362(10) Uani 1 1 d . . .
C1S C 0.5020(18) 0.5094(15) 0.4691(8) 0.082(5) Uani 0.50 1 d PGDU A -1
C2S C 0.3898(13) 0.4804(17) 0.5300(11) 0.091(6) Uani 0.50 1 d PGDU A -1
H2SA H 0.2674 0.4788 0.5144 0.109 Uiso 0.50 1 calc PR A -1
C3S C 0.4605(18) 0.4540(15) 0.6143(9) 0.100(7) Uani 0.50 1 d PGDU A -1
H3SA H 0.3855 0.4346 0.6551 0.120 Uiso 0.50 1 calc PR A -1
N4S N 0.6434(19) 0.4565(14) 0.6377(7) 0.113(8) Uani 0.50 1 d PGDU A -1
C5S C 0.7556(13) 0.4855(12) 0.5767(9) 0.092(5) Uani 0.50 1 d PGDU A -1
H5SA H 0.8780 0.4872 0.5923 0.111 Uiso 0.50 1 calc PR A -1
C6S C 0.6849(16) 0.5119(11) 0.4925(8) 0.103(7) Uani 0.50 1 d PGDU A -1
H6SA H 0.7599 0.5313 0.4517 0.124 Uiso 0.50 1 calc PR A -1
C7S C 0.416(5) 0.535(3) 0.380(2) 0.150(13) Uani 0.50 1 d PDU A -1
H7SA H 0.2899 0.5285 0.3787 0.224 Uiso 0.50 1 calc PR A -1
H7SB H 0.4316 0.4713 0.3320 0.224 Uiso 0.50 1 calc PR A -1
H7SC H 0.4719 0.6207 0.3730 0.224 Uiso 0.50 1 calc PR A -1


_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 C4 1.894(5) . ?
Br2 C6 1.894(4) . ?
Br3 C15 1.902(6) . ?
Br4 C17 1.883(5) . ?
S1 C9 1.798(5) . ?
S1 C20 1.819(5) . ?
N1 C8 1.316(6) . ?
N1 C7 1.364(6) . ?
N2 C19 1.328(6) . ?
N2 C18 1.351(6) . ?
C1 C22 1.381(7) . ?
C1 C2 1.392(7) . ?
C2 C3 1.416(7) . ?
C2 C7 1.423(6) . ?
C3 C4 1.352(7) . ?
C4 C5 1.404(7) . ?
C5 C6 1.377(7) . ?
C6 C7 1.407(7) . ?
C8 C22 1.420(6) . ?
C8 C9 1.531(7) . ?
C9 C10 1.517(7) . ?
C10 C11 1.516(6) . ?
C11 C12 1.384(7) . ?
C11 C19 1.425(6) . ?
C12 C13 1.392(7) . ?
C13 C18 1.409(7) . ?
C13 C14 1.415(7) . ?
C14 C15 1.349(8) . ?
C15 C16 1.391(8) . ?
C16 C17 1.353(7) . ?
C17 C18 1.439(7) . ?
C19 C20 1.507(7) . ?
C20 C21 1.519(7) . ?
C21 C22 1.510(7) . ?
C1S C2S 1.3900 . ?
C1S C6S 1.3900 . ?
C1S C7S 1.48(3) . ?
C2S C3S 1.3900 . ?
C3S N4S 1.3900 . ?
N4S C5S 1.3900 . ?
C5S C6S 1.3900 . ?

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
C9 S1 C20 93.1(2) . . ?
C8 N1 C7 118.5(4) . . ?
C19 N2 C18 118.5(4) . . ?
C22 C1 C2 121.5(4) . . ?
C1 C2 C3 122.4(4) . . ?
C1 C2 C7 117.1(4) . . ?
C3 C2 C7 120.4(4) . . ?
C4 C3 C2 119.3(4) . . ?
C3 C4 C5 122.3(5) . . ?
C3 C4 Br1 119.8(4) . . ?
C5 C4 Br1 117.8(4) . . ?
C6 C5 C4 118.5(5) . . ?
C5 C6 C7 122.2(4) . . ?
C5 C6 Br2 118.4(4) . . ?
C7 C6 Br2 119.3(4) . . ?
N1 C7 C6 120.6(4) . . ?
N1 C7 C2 122.1(4) . . ?
C6 C7 C2 117.3(4) . . ?
N1 C8 C22 124.1(4) . . ?
N1 C8 C9 113.8(4) . . ?
C22 C8 C9 122.0(4) . . ?
C10 C9 C8 109.9(4) . . ?
C10 C9 S1 108.9(3) . . ?
C8 C9 S1 114.6(3) . . ?
C11 C10 C9 113.2(4) . . ?
C12 C11 C19 117.1(4) . . ?
C12 C11 C10 120.3(4) . . ?
C19 C11 C10 122.7(4) . . ?
C11 C12 C13 121.0(5) . . ?
C12 C13 C18 117.3(5) . . ?
C12 C13 C14 121.7(5) . . ?
C18 C13 C14 120.9(5) . . ?
C15 C14 C13 119.1(5) . . ?
C14 C15 C16 122.5(5) . . ?
C14 C15 Br3 119.3(5) . . ?
C16 C15 Br3 118.3(5) . . ?
C17 C16 C15 119.2(5) . . ?
C16 C17 C18 122.0(5) . . ?
C16 C17 Br4 119.4(4) . . ?
C18 C17 Br4 118.6(4) . . ?
N2 C18 C13 123.0(4) . . ?
N2 C18 C17 120.7(4) . . ?
C13 C18 C17 116.4(5) . . ?
N2 C19 C11 123.2(4) . . ?
N2 C19 C20 113.9(4) . . ?
C11 C19 C20 122.8(4) . . ?
C19 C20 C21 111.5(4) . . ?
C19 C20 S1 114.1(3) . . ?
C21 C20 S1 108.3(3) . . ?
C22 C21 C20 113.1(4) . . ?
C1 C22 C8 116.8(4) . . ?
C1 C22 C21 119.8(4) . . ?
C8 C22 C21 123.4(4) . . ?
C2S C1S C6S 120.0 . . ?
C2S C1S C7S 116.8(15) . . ?
C6S C1S C7S 123.2(15) . . ?
C1S C2S C3S 120.0 . . ?
N4S C3S C2S 120.0 . . ?
C3S N4S C5S 120.0 . . ?
C6S C5S N4S 120.0 . . ?
C5S C6S C1S 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.148
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.131
####################################################################### 
# 
# 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_DRB319
_database_code_depnum_ccdc_archive 'CCDC 1419536'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_audit_creation_method           'RAELSPUB and manual entry'
_computing_data_collection       'CAD4 Version 5.0, 1989'
_computing_cell_refinement       'CAD4 Version 5.0, 1989'
_computing_data_reduction        'Local program'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement  'RAELS, (Rae, 1989)'
_computing_molecular_graphics    'ORTEP-II, (Johnson, 1976)'
_computing_publication_material  'Local programs'

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H12 Br4 N2 S,0.5(C10 H20)'
_chemical_formula_sum            'C27 H22 Br4 N2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         726.2

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   9.488(4)
_cell_length_b                   10.506(6)
_cell_length_c                   13.679(8)
_cell_angle_alpha                88.73(4)
_cell_angle_beta                 76.54(4)
_cell_angle_gamma                78.50(4)
_cell_volume                     1299(1)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10
_cell_measurement_theta_min      10
_cell_measurement_theta_max      11
_cell_measurement_temperature    294
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_size_rad          ?
_exptl_crystal_density_diffrn    1.86
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708.0
_exptl_absorpt_coefficient_mu    6.239
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(DeMeulenaer & Tompa, 1965)'
_exptl_absorpt_correction_T_min  0.22
_exptl_absorpt_correction_T_max  0.50

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_diffrn_ambient_temperature      294
_diffrn_reflns_number            4885
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_theta_max         25
_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1.00
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         1
_diffrn_standards_interval_time  30min
_diffrn_standards_decay_%        0

# REFINEMENT DATA

_refine_special_details          ?
_reflns_number_total             4581
_reflns_number_gt                2605
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.048
_refine_ls_wR_factor_ref         0.051
_refine_ls_abs_structure_Flack   ?
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         2605
_refine_ls_number_parameters     186
_refine_ls_goodness_of_fit_ref   1.45
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0004F²]'
_refine_ls_shift/su_max          0.005
_refine_diff_density_max         0.98
_refine_diff_density_min         -1.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_atom_type_scat_source           
'International Tables for X-ray Crystallography, Vol. IV'

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_type_symbol
_atom_site_occupancy
Br1 0.18029(10) 0.31504(10) 1.04083(6) 0.0778(3) Uani Br 1.0
Br2 0.21581(14) -0.18666(12) 0.89104(8) 0.1069(5) Uani Br 1.0
Br3 1.14475(11) 0.23266(9) 0.37674(7) 0.0759(3) Uani Br 1.0
Br4 0.71444(11) 0.58264(11) 0.23277(7) 0.0895(4) Uani Br 1.0
S1 0.8936(2) 0.3689(2) 0.8705(2) 0.0612(8) Uani S 1.0
N1 0.5037(6) 0.2693(6) 0.9242(4) 0.050(2) Uani N 1.0
N2 0.9429(6) 0.3248(5) 0.5801(4) 0.046(1) Uani N 1.0
C1 0.6938(8) 0.3914(8) 0.8841(5) 0.052(1) Uani C 1.0
C2 0.6446(8) 0.2634(7) 0.8779(5) 0.049(1) Uani C 1.0
C3 0.7355(8) 0.1539(8) 0.8225(5) 0.0526(8) Uani C 1.0
C4 0.8932(8) 0.1489(8) 0.7704(6) 0.056(1) Uani C 1.0
C5 0.9361(8) 0.2818(8) 0.7519(5) 0.054(1) Uani C 1.0
C6 0.8674(8) 0.3556(7) 0.6731(5) 0.049(2) Uani C 1.0
C7 0.7295(8) 0.4451(7) 0.6999(5) 0.048(1) Uani C 1.0
C8 0.6500(8) 0.4858(7) 0.8059(5) 0.050(1) Uani C 1.0
C9 0.4433(9) 0.1632(8) 0.9178(5) 0.054(1) Uani C 1.0
C10 0.2923(8) 0.1666(8) 0.9658(5) 0.060(2) Uani C 1.0
C11 0.2255(9) 0.0650(9) 0.9575(6) 0.068(2) Uani C 1.0
C12 0.3115(10) -0.0470(9) 0.9028(6) 0.072(2) Uani C 1.0
C13 0.4574(10) -0.0585(8) 0.8585(6) 0.068(2) Uani C 1.0
C14 0.5241(9) 0.0499(8) 0.8652(6) 0.058(1) Uani C 1.0
C15 0.6734(9) 0.0486(8) 0.8197(6) 0.058(2) Uani C 1.0
C16 0.8866(8) 0.3845(7) 0.5029(5) 0.047(1) Uani C 1.0
C17 0.9655(8) 0.3549(7) 0.4029(5) 0.052(1) Uani C 1.0
C18 0.9148(9) 0.4128(8) 0.3235(5) 0.058(1) Uani C 1.0
C19 0.7811(9) 0.5007(8) 0.3450(6) 0.062(1) Uani C 1.0
C20 0.7003(8) 0.5329(8) 0.4379(6) 0.059(1) Uani C 1.0
C21 0.7518(8) 0.4732(7) 0.5213(5) 0.050(1) Uani C 1.0
C22 0.6749(8) 0.5025(7) 0.6214(5) 0.052(2) Uani C 1.0
C1T 0.4805(13) 0.0121(14) 0.4982(10) 0.054(5) Uani C 0.5
C2T 0.5507(15) 0.0630(14) 0.5748(9) 0.077(5) Uani C 0.5
C3T 0.6605(15) 0.1463(13) 0.5251(11) 0.105(8) Uani C 0.5
C4T 0.7778(13) 0.0722(14) 0.4388(11) 0.093(7) Uani C 0.5
C5T 0.7076(14) 0.0213(14) 0.3623(9) 0.101(8) Uani C 0.5
C6T 0.5978(15) -0.0620(13) 0.4119(10) 0.081(6) Uani C 0.5
C7T 0.3576(11) -0.0673(9) 0.5453(7) 0.062(5) Uani C 0.5
C8T 0.4196(17) -0.1854(14) 0.5986(11) 0.075(7) Uani C 0.5
C9T 0.2943(20) -0.1098(18) 0.4627(12) 0.100(5) Uani C 0.5
C10T 0.2369(19) 0.0211(15) 0.6197(13) 0.099(9) Uani C 0.5
HC1 0.6441 0.4321 0.9520 0.056 Uani H 1.0
H1C4 0.9126 0.1030 0.7039 0.056 Uani H 1.0
H2C4 0.9568 0.0983 0.8126 0.064 Uani H 1.0
HC5 1.0459 0.2660 0.7257 0.058 Uani H 1.0
H1C8 0.5415 0.4947 0.8116 0.048 Uani H 1.0
H2C8 0.6715 0.5718 0.8206 0.056 Uani H 1.0
HC11 0.1184 0.0700 0.9894 0.076 Uani H 1.0
HC13 0.5161 -0.1407 0.8221 0.077 Uani H 1.0
HC15 0.7360 -0.0326 0.7840 0.067 Uani H 1.0
HC18 0.9722 0.3922 0.2526 0.064 Uani H 1.0
HC20 0.6051 0.5980 0.4490 0.068 Uani H 1.0
HC22 0.5787 0.5663 0.6360 0.059 Uani H 1.0
HC1T 0.4294 0.0904 0.4681 0.075 Uani H 0.5
H1C2T 0.6036 -0.0123 0.6069 0.091 Uani H 0.5
H2C2T 0.4713 0.1166 0.6274 0.111 Uani H 0.5
H1C3T 0.7100 0.1723 0.5764 0.152 Uani H 0.5
H2C3T 0.6061 0.2258 0.4984 0.134 Uani H 0.5
H1C4T 0.8383 -0.0028 0.4664 0.102 Uani H 0.5
H2C4T 0.8432 0.1317 0.4048 0.126 Uani H 0.5
H1C5T 0.7871 -0.0324 0.3096 0.144 Uani H 0.5
H2C5T 0.6547 0.0966 0.3302 0.129 Uani H 0.5
H1C6T 0.6523 -0.1415 0.4386 0.095 Uani H 0.5
H2C6T 0.5483 -0.0881 0.3607 0.120 Uani H 0.5
H1C8T 0.3392 -0.2336 0.6277 0.090 Uani H 0.5
H2C8T 0.5002 -0.2435 0.5496 0.088 Uani H 0.5
H3C8T 0.4604 -0.1573 0.6539 0.091 Uani H 0.5
H1C9T 0.2162 -0.1602 0.4921 0.128 Uani H 0.5
H2C9T 0.2499 -0.0315 0.4291 0.126 Uani H 0.5
H3C9T 0.3748 -0.1657 0.4121 0.110 Uani H 0.5
H1C10T 0.1575 -0.0272 0.6507 0.128 Uani H 0.5
H2C10T 0.2793 0.0510 0.6735 0.110 Uani H 0.5
H3C10T 0.1941 0.0982 0.5842 0.123 Uani H 0.5

# MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.875(9) 1_555 1_555 no
Br2 C12 1.901(8) 1_555 1_555 no
Br3 C17 1.881(8) 1_555 1_555 no
Br4 C19 1.917(7) 1_555 1_555 no
S1 C1 1.828(7) 1_555 1_555 no
S1 C5 1.802(8) 1_555 1_555 no
N1 C2 1.330(8) 1_555 1_555 no
N1 C9 1.364(9) 1_555 1_555 no
N2 C6 1.319(8) 1_555 1_555 no
N2 C16 1.376(8) 1_555 1_555 no
C1 C2 1.520(10) 1_555 1_555 no
C1 C8 1.515(10) 1_555 1_555 no
C2 C3 1.407(10) 1_555 1_555 no
C3 C4 1.490(10) 1_555 1_555 no
C3 C15 1.358(10) 1_555 1_555 no
C4 C5 1.531(10) 1_555 1_555 no
C5 C6 1.509(9) 1_555 1_555 no
C6 C7 1.425(10) 1_555 1_555 no
C7 C8 1.498(9) 1_555 1_555 no
C7 C22 1.375(9) 1_555 1_555 no
C9 C10 1.424(11) 1_555 1_555 no
C10 C11 1.365(10) 1_555 1_555 no
C11 C12 1.408(10) 1_555 1_555 no
C12 C13 1.358(10) 1_555 1_555 no
C13 C14 1.423(11) 1_555 1_555 no
C14 C15 1.406(10) 1_555 1_555 no
C16 C17 1.406(9) 1_555 1_555 no
C16 C21 1.397(10) 1_555 1_555 no
C17 C18 1.371(10) 1_555 1_555 no
C18 C19 1.386(11) 1_555 1_555 no
C19 C20 1.334(10) 1_555 1_555 no
C20 C21 1.428(10) 1_555 1_555 no
C21 C22 1.402(10) 1_555 1_555 no
C1T C2T 1.523(12) 1_555 1_555 no
C2T C3T 1.523(12) 1_555 1_555 no
C3T C4T 1.524(13) 1_555 1_555 no
C4T C5T 1.522(13) 1_555 1_555 no
C5T C6T 1.523(12) 1_555 1_555 no
C6T C1T 1.524(12) 1_555 1_555 no
C1T C7T 1.576(14) 1_555 1_555 no
C7T C8T 1.512(16) 1_555 1_555 no
C7T C9T 1.511(16) 1_555 1_555 no
C7T C10T 1.512(17) 1_555 1_555 no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C5 93.4(4) 1_555 1_555 1_555 no
S1 C1 C2 112.2(5) 1_555 1_555 1_555 no
S1 C1 C8 108.5(5) 1_555 1_555 1_555 no
C2 C1 C8 112.4(5) 1_555 1_555 1_555 no
S1 C5 C4 108.8(5) 1_555 1_555 1_555 no
S1 C5 C6 113.8(5) 1_555 1_555 1_555 no
C1 C2 C3 123.3(6) 1_555 1_555 1_555 no
C1 C2 N1 112.7(6) 1_555 1_555 1_555 no
C3 C2 N1 123.8(5) 1_555 1_555 1_555 no
C2 C3 C4 123.3(6) 1_555 1_555 1_555 no
C2 C3 C15 116.5(5) 1_555 1_555 1_555 no
C4 C3 C15 120.2(6) 1_555 1_555 1_555 no
C3 C4 C5 114.6(6) 1_555 1_555 1_555 no
C4 C5 C6 112.1(7) 1_555 1_555 1_555 no
C5 C6 C7 121.3(6) 1_555 1_555 1_555 no
C5 C6 N2 113.9(6) 1_555 1_555 1_555 no
C7 C6 N2 124.7(5) 1_555 1_555 1_555 no
C6 C7 C8 124.0(6) 1_555 1_555 1_555 no
C6 C7 C22 116.1(6) 1_555 1_555 1_555 no
C8 C7 C22 119.7(6) 1_555 1_555 1_555 no
C1 C8 C7 114.2(5) 1_555 1_555 1_555 no
N1 C9 C10 119.7(6) 1_555 1_555 1_555 no
N1 C9 C14 122.3(5) 1_555 1_555 1_555 no
C10 C9 C14 117.9(6) 1_555 1_555 1_555 no
C9 C10 BR1 119.6(4) 1_555 1_555 1_555 no
C9 C10 C11 121.7(6) 1_555 1_555 1_555 no
C11 C10 BR1 118.7(4) 1_555 1_555 1_555 no
C10 C11 C12 118.2(7) 1_555 1_555 1_555 no
C11 C12 BR2 117.5(4) 1_555 1_555 1_555 no
C11 C12 C13 123.0(6) 1_555 1_555 1_555 no
C13 C12 BR2 120.1(4) 1_555 1_555 1_555 no
C12 C13 C14 118.0(6) 1_555 1_555 1_555 no
C13 C14 C15 122.2(7) 1_555 1_555 1_555 no
C9 C14 C15 116.7(6) 1_555 1_555 1_555 no
C9 C14 C13 121.1(5) 1_555 1_555 1_555 no
C14 C15 C3 122.2(7) 1_555 1_555 1_555 no
N2 C16 C17 119.4(5) 1_555 1_555 1_555 no
N2 C16 C21 121.6(5) 1_555 1_555 1_555 no
C17 C16 C21 119.0(6) 1_555 1_555 1_555 no
C16 C17 BR3 119.5(4) 1_555 1_555 1_555 no
C16 C17 C18 121.6(6) 1_555 1_555 1_555 no
C18 C17 BR3 118.9(4) 1_555 1_555 1_555 no
C17 C18 C19 117.6(6) 1_555 1_555 1_555 no
C18 C19 BR4 116.8(4) 1_555 1_555 1_555 no
C18 C19 C20 124.0(7) 1_555 1_555 1_555 no
C20 C19 BR4 119.3(4) 1_555 1_555 1_555 no
C19 C20 C21 119.0(6) 1_555 1_555 1_555 no
C20 C21 C22 122.8(7) 1_555 1_555 1_555 no
C20 C21 C16 118.8(7) 1_555 1_555 1_555 no
C22 C21 C16 118.3(6) 1_555 1_555 1_555 no
C2 N1 C9 118.3(5) 1_555 1_555 1_555 no
C6 N2 C16 118.1(5) 1_555 1_555 1_555 no
C2T C1T C6T 111.2(13) 1_555 1_555 1_555 no
C2T C1T C7T 114.1(13) 1_555 1_555 1_555 no
C6T C1T C7T 112.4(13) 1_555 1_555 1_555 no
C1T C2T C3T 111.2(13) 1_555 1_555 1_555 no
C2T C3T C4T 111.2(13) 1_555 1_555 1_555 no
C3T C4T C5T 111.2(12) 1_555 1_555 1_555 no
C4T C5T C6T 111.2(13) 1_555 1_555 1_555 no
C5T C6T C1T 111.2(13) 1_555 1_555 1_555 no
C1T C7T C8T 111.4(15) 1_555 1_555 1_555 no
C1T C7T C9T 109.1(15) 1_555 1_555 1_555 no
C1T C7T C10T 108.0(15) 1_555 1_555 1_555 no
C8T C7T C9T 109.4(16) 1_555 1_555 1_555 no
C8T C7T C10T 109.4(16) 1_555 1_555 1_555 no
C9T C7T C10T 109.5(16) 1_555 1_555 1_555 no
