# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20141026Feng
_database_code_depnum_ccdc_archive 'CCDC 1456953'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C6 H11 As O3'
_chemical_formula_sum            'C6 H11 As O3'
_chemical_melting_point          ?

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         206.07

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'
As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.0059(10)
_cell_length_b                   11.602(2)
_cell_length_c                   10.6270(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.272(2)
_cell_angle_gamma                90
_cell_volume                     739.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4816
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    4.537
_shelx_estimated_absorpt_T_min   0.210
_shelx_estimated_absorpt_T_max   0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_T_max  0.55
_exptl_absorpt_process_details   
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8432
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.600
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1691
_reflns_number_gt                1568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.4585P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1691
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0555
_refine_ls_wR_factor_gt          0.0546
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
As1 As 0.77408(3) 0.44052(2) 0.60634(2) 0.01457(8) Uani 1 1 d . . . . .
O1 O 0.7335(2) 0.31889(11) 0.50631(12) 0.0154(3) Uani 1 1 d . . . . .
O2 O 0.7471(2) 0.36462(12) 0.75101(12) 0.0182(3) Uani 1 1 d . . . . .
O3 O 1.0716(2) 0.44101(10) 0.61051(14) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.8995(3) 0.22888(16) 0.52295(17) 0.0140(3) Uani 1 1 d . . . . .
H1A H 1.0111 0.2369 0.4574 0.017 Uiso 1 1 calc R U . . .
H1B H 0.8266 0.1529 0.5117 0.017 Uiso 1 1 calc R U . . .
C2 C 0.8446(3) 0.25021(17) 0.75399(17) 0.0164(4) Uani 1 1 d . . . . .
H2A H 0.7247 0.1924 0.7408 0.020 Uiso 1 1 calc R U . . .
H2B H 0.9160 0.2365 0.8382 0.020 Uiso 1 1 calc R U . . .
C3 C 1.1773(3) 0.33703(15) 0.65839(18) 0.0155(4) Uani 1 1 d . . . . .
H3A H 1.2305 0.3499 0.7466 0.019 Uiso 1 1 calc R U . . .
H3B H 1.3085 0.3196 0.6082 0.019 Uiso 1 1 calc R U . . .
C4 C 1.0186(3) 0.23355(15) 0.65335(16) 0.0126(3) Uani 1 1 d . . . . .
C5 C 1.1452(3) 0.12093(16) 0.68165(18) 0.0163(4) Uani 1 1 d . . . . .
H5A H 1.2279 0.1293 0.7636 0.020 Uiso 1 1 calc R U . . .
H5B H 1.0350 0.0583 0.6908 0.020 Uiso 1 1 calc R U . . .
C6 C 1.3100(3) 0.08424(17) 0.58281(19) 0.0178(4) Uani 1 1 d . . . . .
H6A H 1.2291 0.0698 0.5025 0.027 Uiso 1 1 calc R U . . .
H6B H 1.3869 0.0137 0.6108 0.027 Uiso 1 1 calc R U . . .
H6C H 1.4195 0.1457 0.5719 0.027 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
As1 0.01540(12) 0.01314(12) 0.01516(12) -0.00076(7) 0.00028(7) 0.00254(6)
O1 0.0149(6) 0.0153(6) 0.0158(6) -0.0004(5) -0.0029(5) 0.0004(5)
O2 0.0211(7) 0.0204(7) 0.0135(6) 0.0004(5) 0.0044(5) 0.0068(5)
O3 0.0153(6) 0.0113(7) 0.0240(7) 0.0013(5) -0.0017(5) -0.0007(5)
C1 0.0162(8) 0.0133(9) 0.0125(8) -0.0016(7) 0.0000(6) 0.0004(7)
C2 0.0183(9) 0.0177(9) 0.0135(9) 0.0015(7) 0.0036(7) 0.0030(7)
C3 0.0142(8) 0.0121(9) 0.0201(9) -0.0006(7) -0.0020(7) 0.0012(7)
C4 0.0142(8) 0.0133(8) 0.0105(8) -0.0001(6) 0.0013(6) 0.0006(7)
C5 0.0194(9) 0.0141(9) 0.0157(9) 0.0026(7) 0.0024(7) 0.0029(7)
C6 0.0203(9) 0.0139(9) 0.0194(9) -0.0004(7) 0.0030(7) 0.0034(7)

_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
As1 O1 1.7777(13) . ?
As1 O2 1.7847(14) . ?
As1 O3 1.7858(14) . ?
O1 C1 1.450(2) . ?
O2 C2 1.451(2) . ?
O3 C3 1.446(2) . ?
C1 C4 1.535(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C4 1.537(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.533(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.536(2) . ?
C5 C6 1.532(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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
O1 As1 O2 96.23(6) . . ?
O1 As1 O3 97.51(6) . . ?
O2 As1 O3 96.03(6) . . ?
C1 O1 As1 114.93(10) . . ?
C2 O2 As1 114.84(11) . . ?
C3 O3 As1 115.51(11) . . ?
O1 C1 C4 112.22(14) . . ?
O1 C1 H1A 109.2 . . ?
C4 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
C4 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
O2 C2 C4 112.63(15) . . ?
O2 C2 H2A 109.1 . . ?
C4 C2 H2A 109.1 . . ?
O2 C2 H2B 109.1 . . ?
C4 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
O3 C3 C4 112.19(14) . . ?
O3 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
O3 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 C1 109.02(14) . . ?
C3 C4 C5 110.93(15) . . ?
C1 C4 C5 110.87(15) . . ?
C3 C4 C2 108.43(15) . . ?
C1 C4 C2 109.12(15) . . ?
C5 C4 C2 108.42(15) . . ?
C6 C5 C4 115.51(15) . . ?
C6 C5 H5A 108.4 . . ?
C4 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C4 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 As1 O1 C1 -62.17(12) . . . . ?
O3 As1 O1 C1 34.77(12) . . . . ?
O1 As1 O2 C2 37.75(13) . . . . ?
O3 As1 O2 C2 -60.52(13) . . . . ?
O1 As1 O3 C3 -59.04(13) . . . . ?
O2 As1 O3 C3 38.08(13) . . . . ?
As1 O1 C1 C4 22.57(18) . . . . ?
As1 O2 C2 C4 20.13(19) . . . . ?
As1 O3 C3 C4 19.77(19) . . . . ?
O3 C3 C4 C1 47.3(2) . . . . ?
O3 C3 C4 C5 169.67(15) . . . . ?
O3 C3 C4 C2 -71.38(18) . . . . ?
O1 C1 C4 C3 -72.75(18) . . . . ?
O1 C1 C4 C5 164.85(14) . . . . ?
O1 C1 C4 C2 45.51(19) . . . . ?
O2 C2 C4 C3 47.81(19) . . . . ?
O2 C2 C4 C1 -70.81(19) . . . . ?
O2 C2 C4 C5 168.33(15) . . . . ?
C3 C4 C5 C6 -67.0(2) . . . . ?
C1 C4 C5 C6 54.3(2) . . . . ?
C2 C4 C5 C6 174.09(16) . . . . ?

_refine_diff_density_max         0.677
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.090

_shelx_res_file                  
;

    C:\Xtals\jurisson\Anthony\201410~1\20141026Feng.res created by SHELXL-2014/7

REM  20141026Feng in P2(1)/n
REM R1 =  0.0211 for    1568 Fo > 4sig(Fo)  and  0.0234 for all    1691 data
REM     92 parameters refined using      0 restraints
REM Highest difference peak  0.677,  deepest hole -0.542,  1-sigma level  0.090
TITL 20141026Feng in P2(1)/n
CELL 0.71073 6.0059 11.6025 10.6270 90.000 92.272 90.000
ZERR 4.0000 0.0010 0.0020 0.0018 0.000 0.002 0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C H O AS
UNIT 24 44 12 4
MERG 2
FMAP 2
GRID
PLAN -1 0 0
TEMP -173
SIZE 0.15 0.25 0.5
BOND $H
CONF
L.S. 4
ACTA
WGHT    0.031400    0.458500
FVAR       0.22074
AS1   4    0.774079    0.440516    0.606339    11.00000    0.01540    0.01314 =
         0.01516   -0.00076    0.00028    0.00254
O1    3    0.733510    0.318891    0.506310    11.00000    0.01492    0.01526 =
         0.01576   -0.00041   -0.00294    0.00040
O2    3    0.747147    0.364619    0.751011    11.00000    0.02109    0.02041 =
         0.01354    0.00041    0.00438    0.00683
O3    3    1.071612    0.441013    0.610511    11.00000    0.01529    0.01132 =
         0.02402    0.00132   -0.00165   -0.00068
C1    1    0.899542    0.228883    0.522954    11.00000    0.01624    0.01329 =
         0.01249   -0.00163    0.00001    0.00039
AFIX  23
H1A   2    1.011098    0.236852    0.457378    11.00000   -1.20000
H1B   2    0.826610    0.152853    0.511731    11.00000   -1.20000
AFIX   0
C2    1    0.844590    0.250213    0.753990    11.00000    0.01834    0.01769 =
         0.01352    0.00152    0.00361    0.00300
AFIX  23
H2A   2    0.724734    0.192381    0.740781    11.00000   -1.20000
H2B   2    0.916042    0.236517    0.838216    11.00000   -1.20000
AFIX   0
C3    1    1.177268    0.337030    0.658389    11.00000    0.01425    0.01206 =
         0.02012   -0.00063   -0.00205    0.00118
AFIX  23
H3A   2    1.230541    0.349888    0.746626    11.00000   -1.20000
H3B   2    1.308488    0.319600    0.608175    11.00000   -1.20000
AFIX   0
C4    1    1.018580    0.233545    0.653348    11.00000    0.01420    0.01330 =
         0.01051   -0.00005    0.00131    0.00060
C5    1    1.145231    0.120934    0.681650    11.00000    0.01935    0.01410 =
         0.01570    0.00265    0.00237    0.00293
AFIX  23
H5A   2    1.227865    0.129340    0.763606    11.00000   -1.20000
H5B   2    1.035046    0.058323    0.690759    11.00000   -1.20000
AFIX   0
C6    1    1.310020    0.084240    0.582806    11.00000    0.02030    0.01394 =
         0.01937   -0.00038    0.00302    0.00336
AFIX 137
H6A   2    1.229097    0.069820    0.502456    11.00000   -1.50000
H6B   2    1.386893    0.013711    0.610799    11.00000   -1.50000
H6C   2    1.419493    0.145714    0.571927    11.00000   -1.50000
AFIX   0
HKLF 4

REM  20141026Feng in P2(1)/n
REM R1 =  0.0211 for    1568 Fo > 4sig(Fo)  and  0.0234 for all    1691 data
REM     92 parameters refined using      0 restraints

END

WGHT      0.0314      0.4585

REM Highest difference peak  0.677,  deepest hole -0.542,  1-sigma level  0.090
Q1    1   0.9341  0.4410  0.6062  11.00000  0.05    0.68
;
_shelx_res_checksum              72494
_diffrn_standards_decay_%        0.0

