# 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_2011ncs0152aa
_database_code_depnum_ccdc_archive 'CCDC 1020083'
_audit_update_record             
;
2014-08-19 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 As O3 S2'
_chemical_formula_sum            'C21 H21 As O3 S2'
_chemical_formula_weight         460.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   11.687(5)
_cell_length_b                   14.366(6)
_cell_length_c                   12.127(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.254(5)
_cell_angle_gamma                90.00
_cell_volume                     1954.7(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7040
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      31.4

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    1.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5892
_exptl_absorpt_correction_T_max  0.9616
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_source_current           24.0
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: -110.0000 - 70.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -10.0000
	             Phi: 315.0000
	             XTD: 45.0100
	          2theta: -19.9944
scan:
	Number of images: 56
	           Slice: -54.0000 - 2.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -30.0000
	             Phi: 315.0000
	             XTD: 45.0100
	          2theta: -19.9944

;
_diffrn_orient_matrix_UB_11      -0.060696
_diffrn_orient_matrix_UB_12      -0.040867
_diffrn_orient_matrix_UB_13      0.050890
_diffrn_orient_matrix_UB_21      0.027320
_diffrn_orient_matrix_UB_22      0.029911
_diffrn_orient_matrix_UB_23      0.056605
_diffrn_orient_matrix_UB_31      -0.067352
_diffrn_orient_matrix_UB_32      0.053123
_diffrn_orient_matrix_UB_33      0.004437
_diffrn_orient_matrix_type       d*Trek
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10357
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0850
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4425
_reflns_number_gt                3852
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+7.8577P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4425
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0852(4) 0.2610(3) 0.0223(4) 0.0175(10) Uani 1 1 d . . .
H1A H 1.1303 0.2079 0.0655 0.021 Uiso 1 1 calc R . .
H1B H 1.0602 0.2438 -0.0600 0.021 Uiso 1 1 calc R . .
C2 C 1.1673(4) 0.3452(3) 0.0379(5) 0.0189(11) Uani 1 1 d . . .
H2A H 1.1996 0.3593 0.1208 0.023 Uiso 1 1 calc R . .
H2B H 1.1217 0.4001 0.0000 0.023 Uiso 1 1 calc R . .
C3 C 1.2695(4) 0.3257(3) -0.0142(4) 0.0202(11) Uani 1 1 d . . .
H3A H 1.3188 0.3825 -0.0074 0.024 Uiso 1 1 calc R . .
H3B H 1.2356 0.3126 -0.0971 0.024 Uiso 1 1 calc R . .
C4 C 0.8898(4) 0.1613(3) 0.1032(4) 0.0151(10) Uani 1 1 d . . .
C5 C 0.8489(4) 0.1465(3) 0.1987(4) 0.0196(11) Uani 1 1 d . . .
H5 H 0.8452 0.1962 0.2493 0.023 Uiso 1 1 calc R . .
C6 C 0.8134(5) 0.0573(4) 0.2186(5) 0.0238(12) Uani 1 1 d . . .
H6 H 0.7857 0.0456 0.2839 0.029 Uiso 1 1 calc R . .
C7 C 0.8179(4) -0.0141(3) 0.1444(5) 0.0207(11) Uani 1 1 d . . .
H7 H 0.7946 -0.0749 0.1597 0.025 Uiso 1 1 calc R . .
C8 C 0.8559(4) 0.0015(3) 0.0478(5) 0.0220(12) Uani 1 1 d . . .
H8 H 0.8570 -0.0482 -0.0035 0.026 Uiso 1 1 calc R . .
C9 C 0.8926(4) 0.0901(3) 0.0258(4) 0.0183(11) Uani 1 1 d . . .
H9 H 0.9189 0.1017 -0.0403 0.022 Uiso 1 1 calc R . .
C10 C 0.8238(4) 0.3486(3) -0.0372(4) 0.0154(10) Uani 1 1 d . . .
C11 C 0.8406(5) 0.3749(3) -0.1413(4) 0.0190(11) Uani 1 1 d . . .
H11 H 0.9106 0.3570 -0.1611 0.023 Uiso 1 1 calc R . .
C12 C 0.7532(5) 0.4280(3) -0.2164(5) 0.0216(11) Uani 1 1 d . . .
H12 H 0.7630 0.4464 -0.2885 0.026 Uiso 1 1 calc R . .
C13 C 0.6513(4) 0.4541(3) -0.1860(4) 0.0201(11) Uani 1 1 d . . .
H13 H 0.5926 0.4915 -0.2368 0.024 Uiso 1 1 calc R . .
C14 C 0.6351(4) 0.4262(3) -0.0829(5) 0.0206(11) Uani 1 1 d . . .
H14 H 0.5648 0.4438 -0.0636 0.025 Uiso 1 1 calc R . .
C15 C 0.7210(4) 0.3722(3) -0.0067(4) 0.0176(11) Uani 1 1 d . . .
H15 H 0.7098 0.3521 0.0642 0.021 Uiso 1 1 calc R . .
C16 C 0.9876(4) 0.3530(3) 0.2102(4) 0.0186(11) Uani 1 1 d . . .
C17 C 0.9548(4) 0.4453(3) 0.2085(5) 0.0196(11) Uani 1 1 d . . .
H17 H 0.9058 0.4721 0.1399 0.024 Uiso 1 1 calc R . .
C18 C 0.9934(5) 0.4987(4) 0.3071(5) 0.0257(12) Uani 1 1 d . . .
H18 H 0.9711 0.5623 0.3066 0.031 Uiso 1 1 calc R . .
C19 C 1.0651(4) 0.4584(4) 0.4064(5) 0.0244(12) Uani 1 1 d . . .
H19 H 1.0941 0.4952 0.4734 0.029 Uiso 1 1 calc R . .
C20 C 1.0948(5) 0.3649(4) 0.4089(5) 0.0248(12) Uani 1 1 d . . .
H20 H 1.1406 0.3373 0.4785 0.030 Uiso 1 1 calc R . .
C21 C 1.0579(4) 0.3116(4) 0.3106(4) 0.0228(12) Uani 1 1 d . . .
H21 H 1.0800 0.2480 0.3112 0.027 Uiso 1 1 calc R . .
O1 O 1.4228(3) 0.3273(2) 0.2672(3) 0.0222(8) Uani 1 1 d . . .
O2 O 1.5307(3) 0.3774(2) 0.1338(3) 0.0235(8) Uani 1 1 d . . .
O3 O 1.5745(3) 0.2278(3) 0.2301(3) 0.0318(10) Uani 1 1 d . . .
S1 S 1.36565(11) 0.22929(9) 0.05047(12) 0.0232(3) Uani 1 1 d . . .
S2 S 1.48732(11) 0.29986(8) 0.18606(11) 0.0188(3) Uani 1 1 d . . .
As1 As 0.94508(4) 0.28107(3) 0.07280(4) 0.01462(13) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.523(6) . ?
C1 As1 1.923(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.527(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 S1 1.817(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.388(7) . ?
C4 C9 1.395(7) . ?
C4 As1 1.910(5) . ?
C5 C6 1.388(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(7) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.383(7) . ?
C10 C15 1.395(7) . ?
C10 As1 1.916(4) . ?
C11 C12 1.391(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.379(7) . ?
C16 C21 1.396(7) . ?
C16 As1 1.904(5) . ?
C17 C18 1.385(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(7) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
O1 S2 1.452(4) . ?
O2 S2 1.443(4) . ?
O3 S2 1.446(4) . ?
S1 S2 2.1081(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 As1 113.8(3) . . ?
C2 C1 H1A 108.8 . . ?
As1 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
As1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 C3 109.9(4) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C2 C3 S1 115.0(4) . . ?
C2 C3 H3A 108.5 . . ?
S1 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
S1 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C9 121.9(5) . . ?
C5 C4 As1 120.9(4) . . ?
C9 C4 As1 117.3(4) . . ?
C6 C5 C4 118.4(5) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C7 C6 C5 120.4(5) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 121.0(5) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 120.0(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C4 118.3(5) . . ?
C8 C9 H9 120.8 . . ?
C4 C9 H9 120.8 . . ?
C11 C10 C15 122.0(4) . . ?
C11 C10 As1 120.5(4) . . ?
C15 C10 As1 117.5(4) . . ?
C10 C11 C12 118.8(5) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C13 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.5(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.6(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 118.2(5) . . ?
C14 C15 H15 120.9 . . ?
C10 C15 H15 120.9 . . ?
C17 C16 C21 121.0(5) . . ?
C17 C16 As1 120.3(4) . . ?
C21 C16 As1 118.6(4) . . ?
C16 C17 C18 119.9(5) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 119.3(5) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 120.7(5) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 120.2(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C16 118.9(5) . . ?
C20 C21 H21 120.6 . . ?
C16 C21 H21 120.6 . . ?
C3 S1 S2 99.84(17) . . ?
O2 S2 O3 114.6(2) . . ?
O2 S2 O1 113.7(2) . . ?
O3 S2 O1 113.0(2) . . ?
O2 S2 S1 105.78(16) . . ?
O3 S2 S1 101.28(17) . . ?
O1 S2 S1 107.13(16) . . ?
C16 As1 C4 109.8(2) . . ?
C16 As1 C10 107.2(2) . . ?
C4 As1 C10 111.5(2) . . ?
C16 As1 C1 108.8(2) . . ?
C4 As1 C1 106.9(2) . . ?
C10 As1 C1 112.6(2) . . ?

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
As1 C1 C2 C3 -174.9(3) . . . . ?
C1 C2 C3 S1 -61.7(5) . . . . ?
C9 C4 C5 C6 1.9(7) . . . . ?
As1 C4 C5 C6 -177.9(4) . . . . ?
C4 C5 C6 C7 -0.6(8) . . . . ?
C5 C6 C7 C8 -1.0(8) . . . . ?
C6 C7 C8 C9 1.3(8) . . . . ?
C7 C8 C9 C4 0.0(7) . . . . ?
C5 C4 C9 C8 -1.7(7) . . . . ?
As1 C4 C9 C8 178.2(4) . . . . ?
C15 C10 C11 C12 1.3(7) . . . . ?
As1 C10 C11 C12 -176.7(4) . . . . ?
C10 C11 C12 C13 0.3(7) . . . . ?
C11 C12 C13 C14 -1.4(8) . . . . ?
C12 C13 C14 C15 0.8(7) . . . . ?
C13 C14 C15 C10 0.8(7) . . . . ?
C11 C10 C15 C14 -1.8(7) . . . . ?
As1 C10 C15 C14 176.2(3) . . . . ?
C21 C16 C17 C18 1.1(8) . . . . ?
As1 C16 C17 C18 -175.4(4) . . . . ?
C16 C17 C18 C19 0.1(8) . . . . ?
C17 C18 C19 C20 -2.2(8) . . . . ?
C18 C19 C20 C21 3.1(8) . . . . ?
C19 C20 C21 C16 -1.9(8) . . . . ?
C17 C16 C21 C20 -0.2(8) . . . . ?
As1 C16 C21 C20 176.3(4) . . . . ?
C2 C3 S1 S2 -86.9(3) . . . . ?
C3 S1 S2 O2 -52.7(2) . . . . ?
C3 S1 S2 O3 -172.6(3) . . . . ?
C3 S1 S2 O1 68.8(2) . . . . ?
C17 C16 As1 C4 -136.6(4) . . . . ?
C21 C16 As1 C4 46.8(5) . . . . ?
C17 C16 As1 C10 -15.3(5) . . . . ?
C21 C16 As1 C10 168.1(4) . . . . ?
C17 C16 As1 C1 106.7(4) . . . . ?
C21 C16 As1 C1 -69.9(5) . . . . ?
C5 C4 As1 C16 20.8(5) . . . . ?
C9 C4 As1 C16 -159.1(3) . . . . ?
C5 C4 As1 C10 -97.9(4) . . . . ?
C9 C4 As1 C10 82.2(4) . . . . ?
C5 C4 As1 C1 138.7(4) . . . . ?
C9 C4 As1 C1 -41.2(4) . . . . ?
C11 C10 As1 C16 121.6(4) . . . . ?
C15 C10 As1 C16 -56.5(4) . . . . ?
C11 C10 As1 C4 -118.1(4) . . . . ?
C15 C10 As1 C4 63.8(4) . . . . ?
C11 C10 As1 C1 2.0(5) . . . . ?
C15 C10 As1 C1 -176.1(3) . . . . ?
C2 C1 As1 C16 -39.1(4) . . . . ?
C2 C1 As1 C4 -157.7(3) . . . . ?
C2 C1 As1 C10 79.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.644
_refine_diff_density_min         -1.100
_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_2012ncs0291a
_database_code_depnum_ccdc_archive 'CCDC 1020084'
_audit_update_record             
;
2014-08-19 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H24 As O S, Br'
_chemical_formula_sum            'C23 H24 As Br O S'
_chemical_formula_weight         503.31

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'
As As 0.0499 2.0058 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   11.1700(3)
_cell_length_b                   13.6075(4)
_cell_length_c                   14.4757(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.738(7)
_cell_angle_gamma                90.00
_cell_volume                     2199.23(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10344
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.4

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    3.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2658
_exptl_absorpt_correction_T_max  0.6424
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 RX
_diffrn_measurement_device       
;
Crystal Goniometer
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13491
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.44
_reflns_number_total             4973
_reflns_number_gt                4133
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b4 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b4 (Rigaku, 2012)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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 > 2σ(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)+(0.0155P)²+5.1950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4973
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0530
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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
C1 C 0.6685(2) 0.11833(19) 0.13808(16) 0.0183(5) Uani 1 1 d . . .
H1A H 0.5900 0.1516 0.1420 0.022 Uiso 1 1 calc R . .
H1B H 0.7297 0.1696 0.1284 0.022 Uiso 1 1 calc R . .
C2 C 0.6645(3) 0.0501(2) 0.05488(18) 0.0237(6) Uani 1 1 d . . .
H2A H 0.6019 -0.0004 0.0633 0.028 Uiso 1 1 calc R . .
H2B H 0.7425 0.0159 0.0508 0.028 Uiso 1 1 calc R . .
C3 C 0.6381(3) 0.1059(2) -0.03541(18) 0.0258(6) Uani 1 1 d . . .
H3A H 0.5617 0.1421 -0.0301 0.031 Uiso 1 1 calc R . .
H3B H 0.6277 0.0579 -0.0864 0.031 Uiso 1 1 calc R . .
C4 C 0.6847(3) 0.3069(2) -0.04465(18) 0.0264(6) Uani 1 1 d . . .
C5 C 0.7651(3) 0.3928(2) -0.0628(2) 0.0391(8) Uani 1 1 d . . .
H5A H 0.7236 0.4540 -0.0480 0.059 Uiso 1 1 calc R . .
H5B H 0.7859 0.3932 -0.1281 0.059 Uiso 1 1 calc R . .
H5C H 0.8384 0.3872 -0.0241 0.059 Uiso 1 1 calc R . .
C6 C 0.6981(2) 0.15060(18) 0.34844(16) 0.0159(5) Uani 1 1 d . . .
C7 C 0.5994(2) 0.21334(19) 0.35032(17) 0.0192(5) Uani 1 1 d . . .
H7 H 0.5345 0.2057 0.3069 0.023 Uiso 1 1 calc R . .
C8 C 0.5974(2) 0.28699(19) 0.41653(18) 0.0209(5) Uani 1 1 d . . .
H8 H 0.5308 0.3303 0.4183 0.025 Uiso 1 1 calc R . .
C9 C 0.6916(2) 0.29784(19) 0.48010(17) 0.0201(5) Uani 1 1 d . . .
H9 H 0.6895 0.3486 0.5250 0.024 Uiso 1 1 calc R . .
C10 C 0.7891(2) 0.23479(19) 0.47835(17) 0.0201(5) Uani 1 1 d . . .
H10 H 0.8535 0.2426 0.5221 0.024 Uiso 1 1 calc R . .
C11 C 0.7929(2) 0.16033(19) 0.41295(17) 0.0187(5) Uani 1 1 d . . .
H11 H 0.8591 0.1166 0.4121 0.022 Uiso 1 1 calc R . .
C12 C 0.8626(2) -0.00023(19) 0.25257(17) 0.0182(5) Uani 1 1 d . . .
C13 C 0.9481(2) 0.0422(2) 0.19681(19) 0.0247(6) Uani 1 1 d . . .
H13 H 0.9272 0.0948 0.1564 0.030 Uiso 1 1 calc R . .
C14 C 1.0641(3) 0.0061(2) 0.2014(2) 0.0320(7) Uani 1 1 d . . .
H14 H 1.1233 0.0345 0.1639 0.038 Uiso 1 1 calc R . .
C15 C 1.0944(3) -0.0705(2) 0.2597(2) 0.0329(7) Uani 1 1 d . . .
H15 H 1.1744 -0.0943 0.2623 0.040 Uiso 1 1 calc R . .
C16 C 1.0093(3) -0.1132(2) 0.3146(2) 0.0320(7) Uani 1 1 d . . .
H16 H 1.0307 -0.1665 0.3542 0.038 Uiso 1 1 calc R . .
C17 C 0.8924(3) -0.0779(2) 0.31151(19) 0.0242(6) Uani 1 1 d . . .
H17 H 0.8336 -0.1065 0.3492 0.029 Uiso 1 1 calc R . .
C18 C 0.5955(2) -0.05138(18) 0.27951(16) 0.0164(5) Uani 1 1 d . . .
C19 C 0.5949(2) -0.13521(19) 0.22457(17) 0.0214(5) Uani 1 1 d . . .
H19 H 0.6516 -0.1426 0.1774 0.026 Uiso 1 1 calc R . .
C20 C 0.5105(3) -0.2080(2) 0.23951(18) 0.0237(6) Uani 1 1 d . . .
H20 H 0.5079 -0.2647 0.2013 0.028 Uiso 1 1 calc R . .
C21 C 0.4298(2) -0.1983(2) 0.3100(2) 0.0255(6) Uani 1 1 d . . .
H21 H 0.3721 -0.2483 0.3197 0.031 Uiso 1 1 calc R . .
C22 C 0.4332(2) -0.1158(2) 0.3664(2) 0.0259(6) Uani 1 1 d . . .
H22 H 0.3792 -0.1101 0.4155 0.031 Uiso 1 1 calc R . .
C23 C 0.5155(2) -0.0416(2) 0.35116(18) 0.0218(5) Uani 1 1 d . . .
H23 H 0.5174 0.0154 0.3891 0.026 Uiso 1 1 calc R . .
As1 As 0.70427(2) 0.053121(18) 0.253828(17) 0.01479(7) Uani 1 1 d . . .
O1 O 0.58282(19) 0.31459(16) -0.02072(16) 0.0371(5) Uani 1 1 d . . .
S1 S 0.75460(7) 0.19174(6) -0.06393(5) 0.02968(16) Uani 1 1 d . . .
Br1 Br 0.35793(2) 0.12316(2) 0.185616(18) 0.02234(7) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.521(3) . ?
C1 As1 1.927(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.533(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 S1 1.806(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O1 1.204(3) . ?
C4 C5 1.501(4) . ?
C4 S1 1.777(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.396(3) . ?
C6 C7 1.396(4) . ?
C6 As1 1.909(2) . ?
C7 C8 1.387(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.392(4) . ?
C12 C13 1.394(4) . ?
C12 As1 1.912(2) . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.390(4) . ?
C18 C23 1.396(4) . ?
C18 As1 1.914(3) . ?
C19 C20 1.389(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 As1 114.06(18) . . ?
C2 C1 H1A 108.7 . . ?
As1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
As1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 C3 111.9(2) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 S1 113.17(19) . . ?
C2 C3 H3A 108.9 . . ?
S1 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
S1 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
O1 C4 C5 124.0(3) . . ?
O1 C4 S1 123.0(2) . . ?
C5 C4 S1 113.0(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 120.8(2) . . ?
C11 C6 As1 120.18(19) . . ?
C7 C6 As1 118.98(18) . . ?
C8 C7 C6 119.0(2) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 119.2(2) . . ?
C10 C11 H11 120.4 . . ?
C6 C11 H11 120.4 . . ?
C17 C12 C13 120.9(2) . . ?
C17 C12 As1 119.1(2) . . ?
C13 C12 As1 119.9(2) . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 119.3(3) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 120.4 . . ?
C19 C18 C23 120.8(2) . . ?
C19 C18 As1 119.36(19) . . ?
C23 C18 As1 119.84(19) . . ?
C20 C19 C18 119.2(2) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 119.4(2) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?
C6 As1 C12 108.90(10) . . ?
C6 As1 C18 109.88(10) . . ?
C12 As1 C18 108.21(11) . . ?
C6 As1 C1 107.02(11) . . ?
C12 As1 C1 109.52(11) . . ?
C18 As1 C1 113.24(10) . . ?
C4 S1 C3 102.23(14) . . ?

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
As1 C1 C2 C3 -178.94(19) . . . . ?
C1 C2 C3 S1 64.7(3) . . . . ?
C11 C6 C7 C8 1.1(4) . . . . ?
As1 C6 C7 C8 -177.16(19) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C6 0.8(4) . . . . ?
C7 C6 C11 C10 -1.3(4) . . . . ?
As1 C6 C11 C10 176.91(19) . . . . ?
C17 C12 C13 C14 -0.4(4) . . . . ?
As1 C12 C13 C14 176.0(2) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
C15 C16 C17 C12 0.4(4) . . . . ?
C13 C12 C17 C16 0.1(4) . . . . ?
As1 C12 C17 C16 -176.4(2) . . . . ?
C23 C18 C19 C20 2.4(4) . . . . ?
As1 C18 C19 C20 -175.73(19) . . . . ?
C18 C19 C20 C21 -1.7(4) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C20 C21 C22 C23 1.5(4) . . . . ?
C21 C22 C23 C18 -0.8(4) . . . . ?
C19 C18 C23 C22 -1.2(4) . . . . ?
As1 C18 C23 C22 177.0(2) . . . . ?
C11 C6 As1 C12 -11.0(2) . . . . ?
C7 C6 As1 C12 167.21(19) . . . . ?
C11 C6 As1 C18 107.3(2) . . . . ?
C7 C6 As1 C18 -74.4(2) . . . . ?
C11 C6 As1 C1 -129.3(2) . . . . ?
C7 C6 As1 C1 48.9(2) . . . . ?
C17 C12 As1 C6 86.1(2) . . . . ?
C13 C12 As1 C6 -90.5(2) . . . . ?
C17 C12 As1 C18 -33.3(2) . . . . ?
C13 C12 As1 C18 150.1(2) . . . . ?
C17 C12 As1 C1 -157.2(2) . . . . ?
C13 C12 As1 C1 26.3(2) . . . . ?
C19 C18 As1 C6 -173.19(19) . . . . ?
C23 C18 As1 C6 8.6(2) . . . . ?
C19 C18 As1 C12 -54.4(2) . . . . ?
C23 C18 As1 C12 127.4(2) . . . . ?
C19 C18 As1 C1 67.2(2) . . . . ?
C23 C18 As1 C1 -111.0(2) . . . . ?
C2 C1 As1 C6 -177.66(18) . . . . ?
C2 C1 As1 C12 64.4(2) . . . . ?
C2 C1 As1 C18 -56.4(2) . . . . ?
O1 C4 S1 C3 -1.6(3) . . . . ?
C5 C4 S1 C3 179.3(2) . . . . ?
C2 C3 S1 C4 -109.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.105
