# 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_sbmans
_database_code_depnum_ccdc_archive 'CCDC 1578595'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT04171C 2017
_audit_update_record             
;
2017-10-07 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;
_audit_creation_date             2017-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        trisphenylantimony-bis(S-mandelate)
_chemical_formula_moiety         'C34 H29 O6 Sb'
_chemical_formula_sum            'C34 H29 O6 Sb'
_chemical_formula_weight         655.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   14.8251(11)
_cell_length_b                   21.0826(16)
_cell_length_c                   9.1676(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2865.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7775
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.41
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    1.008
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0722 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.9275.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            49524
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.513
_diffrn_reflns_theta_min         2.222
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6612
_reflns_number_total             7276
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.078
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 2696 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         7276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0135P)²+1.4706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0541
_refine_ls_wR_factor_ref         0.0577
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C28(H28), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C2(H2), C6(H6), C3(H3), C30(H30), C26(H26), C33(H33),
 C18(H18), C22(H22), C34(H34), C12(H12), C14(H14), C8(H8), C10(H10), C23(H23),
 C25(H25), C15(H15), C16(H16), C24(H24), C11(H11), C9(H9), C32(H32), C17(H17),
 C31(H31)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6A), O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Sb1 Sb -0.26124(2) -0.13605(2) -0.26145(2) 0.01510(6) Uani 1 1 d . . . . .
C1 C -0.2533(2) -0.23530(14) -0.2526(4) 0.0162(6) Uani 1 1 d . . . . .
C4 C -0.2421(3) -0.36515(18) -0.2460(4) 0.0323(9) Uani 1 1 d . . . . .
H4 H -0.238219 -0.409160 -0.243159 0.039 Uiso 1 1 calc R . . . .
C5 C -0.3244(3) -0.33683(18) -0.2650(5) 0.0286(9) Uani 1 1 d . . . . .
H5 H -0.375796 -0.361580 -0.276847 0.034 Uiso 1 1 calc R . . . .
C2 C -0.1705(2) -0.26436(18) -0.2361(5) 0.0227(8) Uani 1 1 d . . . . .
H2 H -0.118294 -0.240092 -0.228444 0.027 Uiso 1 1 calc R . . . .
C6 C -0.3310(2) -0.27122(18) -0.2666(5) 0.0218(8) Uani 1 1 d . . . . .
H6 H -0.386847 -0.251622 -0.276850 0.026 Uiso 1 1 calc R . . . .
C3 C -0.1657(3) -0.32966(19) -0.2312(5) 0.0288(10) Uani 1 1 d . . . . .
H3 H -0.110307 -0.349529 -0.217788 0.035 Uiso 1 1 calc R . . . .
O1 O -0.38257(17) -0.14766(13) -0.1453(3) 0.0175(6) Uani 1 1 d . . . . .
O2 O -0.14088(16) -0.14217(14) -0.3811(3) 0.0200(6) Uani 1 1 d . . . . .
O4 O -0.09865(19) -0.04050(14) -0.3756(3) 0.0237(6) Uani 1 1 d . . . . .
C27 C -0.0845(3) -0.0962(2) -0.4032(4) 0.0188(9) Uani 1 1 d . . . . .
C30 C 0.0885(3) -0.1291(2) -0.2328(5) 0.0417(12) Uani 1 1 d . . . . .
H30 H 0.085113 -0.085257 -0.223327 0.050 Uiso 1 1 calc R . . . .
C29 C 0.0528(3) -0.1580(2) -0.3527(4) 0.0203(9) Uani 1 1 d . . . . .
C28 C 0.0042(3) -0.11948(19) -0.4681(4) 0.0203(9) Uani 1 1 d . . . . .
H28 H -0.010948 -0.148592 -0.547751 0.024 Uiso 1 1 calc R . . . .
O3 O -0.40310(18) -0.04411(13) -0.1185(3) 0.0214(6) Uani 1 1 d . . . . .
O6 O 0.05507(19) -0.06983(14) -0.5289(3) 0.0245(7) Uani 1 1 d . . . . .
H6A H 0.062051 -0.041822 -0.467927 0.029 Uiso 1 1 calc GR . . . .
C19 C -0.4291(3) -0.0984(2) -0.1042(4) 0.0172(9) Uani 1 1 d . . . . .
C26 C -0.6283(2) -0.10050(19) -0.2498(5) 0.0273(9) Uani 1 1 d . . . . .
H26 H -0.624516 -0.057034 -0.233618 0.033 Uiso 1 1 calc R . . . .
C33 C 0.1002(3) -0.2585(2) -0.2569(6) 0.0350(10) Uani 1 1 d . . . . .
H33 H 0.104459 -0.302279 -0.266521 0.042 Uiso 1 1 calc R . . . .
C21 C -0.5806(2) -0.1416(2) -0.1616(4) 0.0210(8) Uani 1 1 d . . . . .
C13 C -0.1958(3) -0.0932(2) -0.0845(4) 0.0193(8) Uani 1 1 d . . . . .
C18 C -0.1592(3) -0.1327(3) 0.0176(5) 0.0405(12) Uani 1 1 d . . . . .
H18 H -0.165774 -0.176431 0.008604 0.049 Uiso 1 1 calc R . . . .
C22 C -0.5862(3) -0.2062(2) -0.1872(5) 0.0271(10) Uani 1 1 d . . . . .
H22 H -0.554663 -0.234539 -0.128556 0.032 Uiso 1 1 calc R . . . .
C20 C -0.5208(3) -0.11614(18) -0.0408(4) 0.0177(8) Uani 1 1 d . . . . .
H20 H -0.510906 -0.150831 0.028521 0.021 Uiso 1 1 calc R . . . .
C34 C 0.0593(3) -0.2229(2) -0.3648(5) 0.0274(10) Uani 1 1 d . . . . .
H34 H 0.035836 -0.243129 -0.446568 0.033 Uiso 1 1 calc R . . . .
C7 C -0.3300(3) -0.0978(2) -0.4427(4) 0.0187(8) Uani 1 1 d . . . . .
C12 C -0.2838(3) -0.0693(2) -0.5558(5) 0.0347(11) Uani 1 1 d . . . . .
H12 H -0.221749 -0.063283 -0.549178 0.042 Uiso 1 1 calc R . . . .
C14 C -0.1871(3) -0.0285(2) -0.0694(5) 0.0297(10) Uani 1 1 d . . . . .
H14 H -0.212154 -0.001487 -0.138546 0.036 Uiso 1 1 calc R . . . .
C8 C -0.4221(3) -0.1073(2) -0.4541(5) 0.0284(11) Uani 1 1 d . . . . .
H8 H -0.453688 -0.127434 -0.379688 0.034 Uiso 1 1 calc R . . . .
O5 O -0.55960(18) -0.06575(13) 0.0369(3) 0.0199(6) Uani 1 1 d . . . . .
H5A H -0.560466 -0.033956 -0.014635 0.024 Uiso 1 1 calc GR . . . .
C10 C -0.4200(3) -0.0584(2) -0.6903(5) 0.0317(11) Uani 1 1 d . . . . .
H10 H -0.450290 -0.045249 -0.773907 0.038 Uiso 1 1 calc R . . . .
C23 C -0.6390(3) -0.2282(2) -0.3003(5) 0.0352(12) Uani 1 1 d . . . . .
H23 H -0.642217 -0.271553 -0.318041 0.042 Uiso 1 1 calc R . . . .
C25 C -0.6818(3) -0.1233(2) -0.3624(5) 0.0340(12) Uani 1 1 d . . . . .
H25 H -0.714176 -0.095254 -0.420689 0.041 Uiso 1 1 calc R . . . .
C15 C -0.1409(3) -0.0039(2) 0.0487(5) 0.0365(12) Uani 1 1 d . . . . .
H15 H -0.134913 0.039804 0.059148 0.044 Uiso 1 1 calc R . . . .
C16 C -0.1039(3) -0.0439(3) 0.1507(5) 0.0399(13) Uani 1 1 d . . . . .
H16 H -0.073150 -0.027322 0.230516 0.048 Uiso 1 1 calc R . . . .
C24 C -0.6869(3) -0.1871(2) -0.3874(5) 0.0364(12) Uani 1 1 d . . . . .
H24 H -0.722582 -0.202690 -0.462785 0.044 Uiso 1 1 calc R . . . .
C11 C -0.3299(3) -0.0498(2) -0.6789(5) 0.0389(13) Uani 1 1 d . . . . .
H11 H -0.298589 -0.030491 -0.754743 0.047 Uiso 1 1 calc R . . . .
C9 C -0.4666(3) -0.0864(3) -0.5786(5) 0.0367(12) Uani 1 1 d . . . . .
H9 H -0.528690 -0.091563 -0.586122 0.044 Uiso 1 1 calc R . . . .
C32 C 0.1343(4) -0.2294(3) -0.1368(6) 0.0443(14) Uani 1 1 d . . . . .
H32 H 0.160501 -0.253273 -0.062856 0.053 Uiso 1 1 calc R . . . .
C17 C -0.1123(4) -0.1074(3) 0.1347(6) 0.0545(17) Uani 1 1 d . . . . .
H17 H -0.086348 -0.134370 0.203105 0.065 Uiso 1 1 calc R . . . .
C31 C 0.1300(4) -0.1649(3) -0.1250(6) 0.0541(17) Uani 1 1 d . . . . .
H31 H 0.154917 -0.144820 -0.044118 0.065 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 C1 2.097(3) . ?
Sb1 O1 2.105(3) . ?
Sb1 O2 2.099(2) . ?
Sb1 C13 2.095(4) . ?
Sb1 C7 2.110(4) . ?
C1 C2 1.380(4) . ?
C1 C6 1.385(5) . ?
C4 C5 1.370(5) . ?
C4 C3 1.364(5) . ?
C5 C6 1.387(5) . ?
C2 C3 1.379(5) . ?
O1 C19 1.303(5) . ?
O2 C27 1.296(5) . ?
O4 C27 1.220(5) . ?
C27 C28 1.524(5) . ?
C30 C29 1.363(6) . ?
C30 C31 1.387(6) . ?
C29 C28 1.516(5) . ?
C29 C34 1.377(6) . ?
C28 O6 1.405(4) . ?
O3 C19 1.214(5) . ?
C19 C20 1.525(5) . ?
C26 C21 1.379(6) . ?
C26 C25 1.389(6) . ?
C33 C34 1.381(6) . ?
C33 C32 1.358(7) . ?
C21 C22 1.385(6) . ?
C21 C20 1.516(5) . ?
C13 C18 1.365(6) . ?
C13 C14 1.377(6) . ?
C18 C17 1.386(6) . ?
C22 C23 1.379(6) . ?
C20 O5 1.402(4) . ?
C7 C12 1.380(5) . ?
C7 C8 1.384(6) . ?
C12 C11 1.383(6) . ?
C14 C15 1.383(6) . ?
C8 C9 1.390(6) . ?
C10 C11 1.352(6) . ?
C10 C9 1.370(6) . ?
C23 C24 1.375(7) . ?
C25 C24 1.367(7) . ?
C15 C16 1.373(7) . ?
C16 C17 1.353(7) . ?
C32 C31 1.365(7) . ?

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
C1 Sb1 O1 84.97(11) . . ?
C1 Sb1 O2 84.90(12) . . ?
C1 Sb1 C7 116.07(14) . . ?
O1 Sb1 C7 91.74(13) . . ?
O2 Sb1 O1 169.75(11) . . ?
O2 Sb1 C7 91.28(13) . . ?
C13 Sb1 C1 111.96(15) . . ?
C13 Sb1 O1 93.09(13) . . ?
C13 Sb1 O2 92.16(12) . . ?
C13 Sb1 C7 131.96(16) . . ?
C2 C1 Sb1 119.8(2) . . ?
C2 C1 C6 120.5(3) . . ?
C6 C1 Sb1 119.7(2) . . ?
C3 C4 C5 120.9(4) . . ?
C4 C5 C6 119.9(4) . . ?
C3 C2 C1 119.5(3) . . ?
C1 C6 C5 119.0(3) . . ?
C4 C3 C2 120.1(4) . . ?
C19 O1 Sb1 120.4(3) . . ?
C27 O2 Sb1 125.8(3) . . ?
O2 C27 C28 112.2(4) . . ?
O4 C27 O2 125.2(4) . . ?
O4 C27 C28 122.6(4) . . ?
C29 C30 C31 120.3(5) . . ?
C30 C29 C28 120.5(4) . . ?
C30 C29 C34 118.8(4) . . ?
C34 C29 C28 120.6(4) . . ?
C29 C28 C27 108.1(3) . . ?
O6 C28 C27 112.2(3) . . ?
O6 C28 C29 114.9(3) . . ?
O1 C19 C20 112.7(4) . . ?
O3 C19 O1 123.6(4) . . ?
O3 C19 C20 123.7(4) . . ?
C21 C26 C25 120.8(4) . . ?
C32 C33 C34 119.9(4) . . ?
C26 C21 C22 119.1(4) . . ?
C26 C21 C20 120.4(4) . . ?
C22 C21 C20 120.4(4) . . ?
C18 C13 Sb1 116.8(3) . . ?
C18 C13 C14 119.9(4) . . ?
C14 C13 Sb1 123.2(3) . . ?
C13 C18 C17 119.7(5) . . ?
C23 C22 C21 119.5(4) . . ?
C21 C20 C19 109.2(3) . . ?
O5 C20 C19 111.9(3) . . ?
O5 C20 C21 113.5(3) . . ?
C29 C34 C33 120.8(4) . . ?
C12 C7 Sb1 121.2(3) . . ?
C12 C7 C8 119.8(4) . . ?
C8 C7 Sb1 118.7(3) . . ?
C7 C12 C11 119.8(4) . . ?
C13 C14 C15 119.8(4) . . ?
C7 C8 C9 118.9(4) . . ?
C11 C10 C9 119.8(4) . . ?
C24 C23 C22 121.2(4) . . ?
C24 C25 C26 119.8(4) . . ?
C16 C15 C14 120.0(5) . . ?
C17 C16 C15 119.8(4) . . ?
C25 C24 C23 119.6(4) . . ?
C10 C11 C12 120.8(4) . . ?
C10 C9 C8 120.8(4) . . ?
C33 C32 C31 119.8(5) . . ?
C16 C17 C18 120.8(5) . . ?
C32 C31 C30 120.4(5) . . ?

_olex2_submission_original_sample_id Sb
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# 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_bims
_database_code_depnum_ccdc_archive 'CCDC 1580805'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT04171C 2017
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;
_audit_creation_date             2017-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        trisphenylbismuth-bis(S-mandelate)
_chemical_formula_moiety         'C34 H29 Bi O6'
_chemical_formula_sum            'C34 H29 Bi O6'
_chemical_formula_weight         742.55
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Bi Bi -4.1077 10.2566 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.2304(3)
_cell_length_b                   11.9959(5)
_cell_length_c                   23.2353(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2851.50(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4805
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.229
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0952 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.7708.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24864
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.873
_diffrn_reflns_theta_min         2.441
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5986
_reflns_number_total             6790
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details 
;
 Flack x determined using 2439 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         6790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      0.877
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0499
_refine_ls_wR_factor_ref         0.0526
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00I(H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014),
 C015(H015)
2.c Idealised tetrahedral OH refined as rotating group:
 O006(H006), O00B(H00B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Bi01 Bi 0.62161(2) 0.71250(2) 0.71031(2) 0.01132(6) Uani 1 1 d . . . . .
O002 O 0.7906(4) 0.8273(4) 0.63586(18) 0.0173(10) Uani 1 1 d . . . . .
O003 O 0.5748(4) 0.8485(4) 0.64236(18) 0.0175(11) Uani 1 1 d . . . . .
O004 O 0.8679(5) 0.6045(4) 0.75739(17) 0.0186(10) Uani 1 1 d . . . . .
O005 O 0.6586(3) 0.5848(4) 0.78126(18) 0.0128(10) Uani 1 1 d . . . . .
O006 O 0.8172(4) 1.0018(5) 0.5659(2) 0.0242(12) Uani 1 1 d . . . . .
H006 H 0.866627 0.970159 0.588342 0.036 Uiso 1 1 calc GR . . . .
C007 C 0.7169(6) 0.8363(6) 0.7659(3) 0.0131(13) Uani 1 1 d . . . . .
C008 C 0.6872(6) 0.8714(6) 0.6208(3) 0.0158(14) Uani 1 1 d . . . . .
C009 C 0.6901(6) 0.9572(6) 0.5715(3) 0.0157(15) Uani 1 1 d . . . . .
H009 H 0.628300 1.017473 0.579818 0.019 Uiso 1 1 calc R . . . .
C00A C 0.6502(6) 0.5914(6) 0.6397(3) 0.0161(15) Uani 1 1 d . . . . .
O00B O 0.9542(4) 0.5068(5) 0.8518(2) 0.0258(12) Uani 1 1 d . . . . .
H00B H 0.988311 0.527667 0.821704 0.039 Uiso 1 1 calc GR . . . .
C00C C 0.7814(5) 0.5773(5) 0.7920(3) 0.0153(12) Uani 1 1 d . . . . .
C00D C 0.6474(6) 0.8962(5) 0.5171(3) 0.0153(14) Uani 1 1 d . . . . .
C00E C 0.5936(6) 0.6139(6) 0.5877(3) 0.0220(16) Uani 1 1 d . . . . .
H00E H 0.548498 0.680219 0.581885 0.026 Uiso 1 1 calc R . . . .
C00F C 0.6372(7) 0.8828(6) 0.8069(3) 0.0193(15) Uani 1 1 d . . . . .
H00F H 0.550247 0.860913 0.810006 0.023 Uiso 1 1 calc R . . . .
C00G C 0.8840(8) 0.7065(6) 0.9108(2) 0.0283(15) Uani 1 1 d . . . . .
H00G H 0.970160 0.697999 0.898751 0.034 Uiso 1 1 calc R . . . .
C00H C 0.6047(7) 0.5363(6) 0.5440(3) 0.0270(17) Uani 1 1 d . . . . .
H00H H 0.566447 0.550464 0.508425 0.032 Uiso 1 1 calc R . . . .
C00I C 0.8211(6) 0.5376(6) 0.8520(3) 0.0166(15) Uani 1 1 d . . . . .
H00I H 0.768361 0.472329 0.862160 0.020 Uiso 1 1 calc R . . . .
C00J C 0.7903(6) 0.6307(6) 0.8935(3) 0.0178(14) Uani 1 1 d . . . . .
C00K C 0.4149(5) 0.7122(6) 0.7379(2) 0.0138(12) Uani 1 1 d . . . . .
C00L C 0.8454(6) 0.8664(6) 0.7595(3) 0.0177(15) Uani 1 1 d . . . . .
H00L H 0.897388 0.834025 0.731282 0.021 Uiso 1 1 calc R . . . .
C00M C 0.6723(7) 0.4379(7) 0.5527(3) 0.0296(18) Uani 1 1 d . . . . .
H00M H 0.679430 0.385989 0.523106 0.036 Uiso 1 1 calc R . . . .
C00N C 0.3765(7) 0.6437(5) 0.7821(3) 0.0221(13) Uani 1 1 d . . . . .
H00N H 0.435117 0.594208 0.798904 0.027 Uiso 1 1 calc R . . . .
C00O C 0.7288(7) 0.4172(7) 0.6054(3) 0.0292(18) Uani 1 1 d . . . . .
H00O H 0.774829 0.351312 0.611323 0.035 Uiso 1 1 calc R . . . .
C00P C 0.6299(10) 0.7324(8) 0.9477(3) 0.048(2) Uani 1 1 d . . . . .
H00P H 0.544348 0.741447 0.960397 0.057 Uiso 1 1 calc R . . . .
C00Q C 0.6622(7) 0.6443(7) 0.9125(3) 0.0299(18) Uani 1 1 d . . . . .
H00Q H 0.598181 0.593723 0.901259 0.036 Uiso 1 1 calc R . . . .
C00R C 0.7354(7) 0.8300(6) 0.4879(3) 0.0213(16) Uani 1 1 d . . . . .
H00R H 0.822514 0.827671 0.499230 0.026 Uiso 1 1 calc R . . . .
C00S C 0.8953(6) 0.9463(6) 0.7964(3) 0.0250(16) Uani 1 1 d . . . . .
H00S H 0.982317 0.967996 0.793258 0.030 Uiso 1 1 calc R . . . .
C00T C 0.6883(7) 0.9634(7) 0.8438(3) 0.0274(18) Uani 1 1 d . . . . .
H00T H 0.636083 0.995776 0.872015 0.033 Uiso 1 1 calc R . . . .
C00U C 0.8500(10) 0.7950(8) 0.9459(3) 0.047(2) Uani 1 1 d . . . . .
H00U H 0.913139 0.846404 0.957108 0.056 Uiso 1 1 calc R . . . .
C00V C 0.3291(5) 0.7856(6) 0.7115(3) 0.0178(12) Uani 1 1 d . . . . .
H00V H 0.356951 0.831766 0.681822 0.021 Uiso 1 1 calc R . . . .
C00W C 0.7177(7) 0.4936(6) 0.6496(3) 0.0242(16) Uani 1 1 d . . . . .
H00W H 0.755090 0.479488 0.685344 0.029 Uiso 1 1 calc R . . . .
C00X C 0.7252(12) 0.8069(8) 0.9640(3) 0.053(3) Uani 1 1 d . . . . .
H00X H 0.703484 0.866359 0.987893 0.064 Uiso 1 1 calc R . . . .
C00Y C 0.6930(7) 0.7670(7) 0.4415(3) 0.0282(19) Uani 1 1 d . . . . .
H00Y H 0.752338 0.721182 0.422518 0.034 Uiso 1 1 calc R . . . .
C00Z C 0.2463(6) 0.6500(7) 0.8012(3) 0.0251(17) Uani 1 1 d . . . . .
H00Z H 0.218806 0.605814 0.831786 0.030 Uiso 1 1 calc R . . . .
C010 C 0.4785(7) 0.8389(7) 0.4513(3) 0.0290(18) Uani 1 1 d . . . . .
H010 H 0.392153 0.842909 0.438925 0.035 Uiso 1 1 calc R . . . .
C011 C 0.5647(7) 0.7706(7) 0.4227(3) 0.0285(19) Uani 1 1 d . . . . .
H011 H 0.537503 0.727850 0.391504 0.034 Uiso 1 1 calc R . . . .
C012 C 0.5179(7) 0.9014(6) 0.4978(3) 0.0232(16) Uani 1 1 d . . . . .
H012 H 0.458214 0.947350 0.516501 0.028 Uiso 1 1 calc R . . . .
C013 C 0.1592(5) 0.7215(6) 0.7749(3) 0.0196(15) Uani 1 1 d . . . . .
H013 H 0.072791 0.724201 0.787226 0.024 Uiso 1 1 calc R . . . .
C014 C 0.8166(7) 0.9941(7) 0.8379(3) 0.0271(18) Uani 1 1 d . . . . .
H014 H 0.851287 1.047988 0.862324 0.033 Uiso 1 1 calc R . . . .
C015 C 0.1998(5) 0.7883(7) 0.7306(3) 0.0202(14) Uani 1 1 d . . . . .
H015 H 0.140469 0.836151 0.713068 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi01 O003 2.320(5) . ?
Bi01 O005 2.282(4) . ?
Bi01 C007 2.197(6) . ?
Bi01 C00A 2.211(7) . ?
Bi01 C00K 2.210(5) . ?
O002 C008 1.234(7) . ?
O003 C008 1.283(7) . ?
O004 C00C 1.239(8) . ?
O005 C00C 1.285(6) . ?
O006 H006 0.8200 . ?
O006 C009 1.412(7) . ?
C007 C00F 1.373(8) . ?
C007 C00L 1.371(8) . ?
C008 C009 1.541(9) . ?
C009 H009 0.9800 . ?
C009 C00D 1.524(9) . ?
C00A C00E 1.366(9) . ?
C00A C00W 1.380(10) . ?
O00B H00B 0.8200 . ?
O00B C00I 1.411(7) . ?
C00C C00I 1.528(9) . ?
C00D C00R 1.379(9) . ?
C00D C012 1.400(9) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.383(9) . ?
C00F H00F 0.9300 . ?
C00F C00T 1.394(9) . ?
C00G H00G 0.9300 . ?
C00G C00J 1.380(9) . ?
C00G C00U 1.384(12) . ?
C00H H00H 0.9300 . ?
C00H C00M 1.383(10) . ?
C00I H00I 0.9800 . ?
C00I C00J 1.509(9) . ?
C00J C00Q 1.392(9) . ?
C00K C00N 1.371(8) . ?
C00K C00V 1.386(8) . ?
C00L H00L 0.9300 . ?
C00L C00S 1.384(9) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.378(10) . ?
C00N H00N 0.9300 . ?
C00N C00Z 1.406(9) . ?
C00O H00O 0.9300 . ?
C00O C00W 1.381(10) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.377(11) . ?
C00P C00X 1.376(13) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00Y 1.386(10) . ?
C00S H00S 0.9300 . ?
C00S C014 1.381(10) . ?
C00T H00T 0.9300 . ?
C00T C014 1.371(10) . ?
C00U H00U 0.9300 . ?
C00U C00X 1.352(13) . ?
C00V H00V 0.9300 . ?
C00V C015 1.395(8) . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
C00Y H00Y 0.9300 . ?
C00Y C011 1.384(9) . ?
C00Z H00Z 0.9300 . ?
C00Z C013 1.379(9) . ?
C010 H010 0.9300 . ?
C010 C011 1.375(11) . ?
C010 C012 1.377(10) . ?
C011 H011 0.9300 . ?
C012 H012 0.9300 . ?
C013 H013 0.9300 . ?
C013 C015 1.368(9) . ?
C014 H014 0.9300 . ?
C015 H015 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O005 Bi01 O003 176.19(15) . . ?
C007 Bi01 O003 90.9(2) . . ?
C007 Bi01 O005 87.44(19) . . ?
C007 Bi01 C00A 145.3(2) . . ?
C007 Bi01 C00K 104.8(2) . . ?
C00A Bi01 O003 89.1(2) . . ?
C00A Bi01 O005 94.17(18) . . ?
C00A Bi01 C00K 109.9(2) . . ?
C00K Bi01 O003 90.1(2) . . ?
C00K Bi01 O005 86.99(19) . . ?
C008 O003 Bi01 103.4(4) . . ?
C00C O005 Bi01 110.4(4) . . ?
C009 O006 H006 109.5 . . ?
C00F C007 Bi01 114.8(4) . . ?
C00L C007 Bi01 122.7(5) . . ?
C00L C007 C00F 122.5(6) . . ?
O002 C008 O003 124.4(6) . . ?
O002 C008 C009 118.7(6) . . ?
O003 C008 C009 116.8(6) . . ?
O006 C009 C008 109.9(5) . . ?
O006 C009 H009 109.4 . . ?
O006 C009 C00D 111.7(5) . . ?
C008 C009 H009 109.4 . . ?
C00D C009 C008 106.9(6) . . ?
C00D C009 H009 109.4 . . ?
C00E C00A Bi01 118.0(5) . . ?
C00E C00A C00W 121.8(7) . . ?
C00W C00A Bi01 120.1(5) . . ?
C00I O00B H00B 109.5 . . ?
O004 C00C O005 123.7(6) . . ?
O004 C00C C00I 119.0(5) . . ?
O005 C00C C00I 117.3(6) . . ?
C00R C00D C009 119.8(6) . . ?
C00R C00D C012 119.1(6) . . ?
C012 C00D C009 121.0(6) . . ?
C00A C00E H00E 120.6 . . ?
C00A C00E C00H 118.8(7) . . ?
C00H C00E H00E 120.6 . . ?
C007 C00F H00F 120.5 . . ?
C007 C00F C00T 119.1(6) . . ?
C00T C00F H00F 120.5 . . ?
C00J C00G H00G 119.9 . . ?
C00J C00G C00U 120.1(8) . . ?
C00U C00G H00G 119.9 . . ?
C00E C00H H00H 119.7 . . ?
C00E C00H C00M 120.5(6) . . ?
C00M C00H H00H 119.7 . . ?
O00B C00I C00C 109.5(5) . . ?
O00B C00I H00I 108.8 . . ?
O00B C00I C00J 113.4(6) . . ?
C00C C00I H00I 108.8 . . ?
C00J C00I C00C 107.3(5) . . ?
C00J C00I H00I 108.8 . . ?
C00G C00J C00I 121.8(6) . . ?
C00G C00J C00Q 119.0(7) . . ?
C00Q C00J C00I 119.0(6) . . ?
C00N C00K Bi01 119.5(5) . . ?
C00N C00K C00V 122.0(5) . . ?
C00V C00K Bi01 118.4(4) . . ?
C007 C00L H00L 121.0 . . ?
C007 C00L C00S 118.0(6) . . ?
C00S C00L H00L 121.0 . . ?
C00H C00M H00M 120.2 . . ?
C00O C00M C00H 119.6(7) . . ?
C00O C00M H00M 120.2 . . ?
C00K C00N H00N 120.8 . . ?
C00K C00N C00Z 118.4(6) . . ?
C00Z C00N H00N 120.8 . . ?
C00M C00O H00O 119.8 . . ?
C00M C00O C00W 120.5(7) . . ?
C00W C00O H00O 119.8 . . ?
C00Q C00P H00P 120.2 . . ?
C00Q C00P C00X 119.5(8) . . ?
C00X C00P H00P 120.2 . . ?
C00J C00Q H00Q 119.9 . . ?
C00P C00Q C00J 120.2(8) . . ?
C00P C00Q H00Q 119.9 . . ?
C00D C00R H00R 120.2 . . ?
C00D C00R C00Y 119.5(6) . . ?
C00Y C00R H00R 120.2 . . ?
C00L C00S H00S 119.8 . . ?
C014 C00S C00L 120.3(6) . . ?
C014 C00S H00S 119.8 . . ?
C00F C00T H00T 120.5 . . ?
C014 C00T C00F 119.0(7) . . ?
C014 C00T H00T 120.5 . . ?
C00G C00U H00U 119.9 . . ?
C00X C00U C00G 120.2(9) . . ?
C00X C00U H00U 119.9 . . ?
C00K C00V H00V 120.9 . . ?
C00K C00V C015 118.3(6) . . ?
C015 C00V H00V 120.9 . . ?
C00A C00W C00O 118.8(7) . . ?
C00A C00W H00W 120.6 . . ?
C00O C00W H00W 120.6 . . ?
C00P C00X H00X 119.5 . . ?
C00U C00X C00P 121.0(8) . . ?
C00U C00X H00X 119.5 . . ?
C00R C00Y H00Y 119.2 . . ?
C011 C00Y C00R 121.7(7) . . ?
C011 C00Y H00Y 119.2 . . ?
C00N C00Z H00Z 119.8 . . ?
C013 C00Z C00N 120.3(6) . . ?
C013 C00Z H00Z 119.8 . . ?
C011 C010 H010 119.4 . . ?
C011 C010 C012 121.1(7) . . ?
C012 C010 H010 119.4 . . ?
C00Y C011 H011 120.8 . . ?
C010 C011 C00Y 118.3(7) . . ?
C010 C011 H011 120.8 . . ?
C00D C012 H012 119.9 . . ?
C010 C012 C00D 120.3(7) . . ?
C010 C012 H012 119.9 . . ?
C00Z C013 H013 120.0 . . ?
C015 C013 C00Z 120.1(6) . . ?
C015 C013 H013 120.0 . . ?
C00S C014 H014 119.4 . . ?
C00T C014 C00S 121.1(7) . . ?
C00T C014 H014 119.4 . . ?
C00V C015 H015 119.6 . . ?
C013 C015 C00V 120.9(6) . . ?
C013 C015 H015 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_vb218reb
_database_code_depnum_ccdc_archive 'CCDC 1578596'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT04171C 2017
_audit_update_record             
;
2017-10-07 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        trisphenylantimony-bis(R-mandelate)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H29 O6 Sb'
_chemical_formula_sum            'C34 H29 O6 Sb'
_chemical_formula_weight         655.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P_21_21_2
_symmetry_space_group_name_Hall  P22ab


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

_cell_length_a                   14.8167(5)
_cell_length_b                   21.1134(7)
_cell_length_c                   9.2070(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2880.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2886
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.09

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7140
_exptl_absorpt_correction_T_max  0.8246
_exptl_absorpt_process_details   'SADABS (Sheldrick 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23795
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         29.78
_reflns_number_total             8210
_reflns_number_gt                7617
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0213P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.024(13)
_refine_ls_number_reflns         8210
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0602
_refine_ls_wR_factor_gt          0.0576
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration ad

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
Sb1 Sb 0.261720(9) 0.136368(7) 0.262604(15) 0.01196(4) Uani 1 1 d . . .
O1 O 0.38342(11) 0.14811(8) 0.14717(19) 0.0143(4) Uani 1 1 d . . .
O2 O 0.40310(12) 0.04436(9) 0.1182(2) 0.0179(4) Uani 1 1 d . . .
O3 O 0.55992(12) 0.06556(9) -0.0365(2) 0.0159(4) Uani 1 1 d . . .
O4 O 0.14088(11) 0.14241(9) 0.38174(18) 0.0166(4) Uani 1 1 d . . .
O5 O 0.09865(12) 0.04086(9) 0.3754(2) 0.0197(4) Uani 1 1 d . . .
O6 O -0.05575(13) 0.06984(10) 0.5279(2) 0.0206(4) Uani 1 1 d . . .
C1 C 0.25377(14) 0.23532(9) 0.2534(2) 0.0142(4) Uani 1 1 d . . .
C2 C 0.17025(16) 0.26436(11) 0.2379(3) 0.0182(5) Uani 1 1 d . . .
H2 H 0.1170 0.2395 0.2310 0.022 Uiso 1 1 calc R . .
C3 C 0.16517(18) 0.32995(12) 0.2327(3) 0.0231(6) Uani 1 1 d . . .
H3 H 0.1084 0.3500 0.2197 0.028 Uiso 1 1 calc R . .
C4 C 0.24220(17) 0.36617(11) 0.2464(2) 0.0263(5) Uani 1 1 d . . .
H4 H 0.2381 0.4111 0.2437 0.032 Uiso 1 1 calc R . .
C5 C 0.32524(17) 0.33739(12) 0.2640(3) 0.0230(5) Uani 1 1 d . . .
H5 H 0.3780 0.3626 0.2747 0.028 Uiso 1 1 calc R . .
C6 C 0.33186(15) 0.27191(11) 0.2660(3) 0.0175(5) Uani 1 1 d . . .
H6 H 0.3891 0.2521 0.2760 0.021 Uiso 1 1 calc R . .
C7 C 0.19604(17) 0.09333(13) 0.0858(3) 0.0157(5) Uani 1 1 d . . .
C8 C 0.1591(2) 0.13372(17) -0.0168(3) 0.0305(6) Uani 1 1 d . . .
H8 H 0.1654 0.1783 -0.0071 0.037 Uiso 1 1 calc R . .
C9 C 0.1127(3) 0.10816(17) -0.1339(4) 0.0397(9) Uani 1 1 d . . .
H9 H 0.0869 0.1356 -0.2042 0.048 Uiso 1 1 calc R . .
C10 C 0.1037(2) 0.04421(17) -0.1495(3) 0.0332(8) Uani 1 1 d . . .
H10 H 0.0719 0.0273 -0.2303 0.040 Uiso 1 1 calc R . .
C11 C 0.1407(2) 0.00455(16) -0.0481(3) 0.0319(7) Uani 1 1 d . . .
H11 H 0.1343 -0.0400 -0.0591 0.038 Uiso 1 1 calc R . .
C12 C 0.1874(2) 0.02833(13) 0.0702(3) 0.0236(6) Uani 1 1 d . . .
H12 H 0.2132 0.0005 0.1398 0.028 Uiso 1 1 calc R . .
C13 C 0.33043(17) 0.09816(12) 0.4434(3) 0.0156(5) Uani 1 1 d . . .
C14 C 0.42313(19) 0.10659(15) 0.4545(3) 0.0209(6) Uani 1 1 d . . .
H14 H 0.4558 0.1263 0.3781 0.025 Uiso 1 1 calc R . .
C15 C 0.4673(2) 0.08594(16) 0.5778(3) 0.0269(7) Uani 1 1 d . . .
H15 H 0.5309 0.0905 0.5847 0.032 Uiso 1 1 calc R . .
C16 C 0.4206(2) 0.05884(14) 0.6906(3) 0.0258(6) Uani 1 1 d . . .
H16 H 0.4517 0.0457 0.7757 0.031 Uiso 1 1 calc R . .
C17 C 0.3285(2) 0.05064(15) 0.6803(3) 0.0283(7) Uani 1 1 d . . .
H17 H 0.2962 0.0316 0.7581 0.034 Uiso 1 1 calc R . .
C18 C 0.2830(2) 0.07007(15) 0.5566(3) 0.0275(7) Uani 1 1 d . . .
H18 H 0.2196 0.0642 0.5492 0.033 Uiso 1 1 calc R . .
C19 C 0.42937(18) 0.09879(13) 0.1053(3) 0.0136(5) Uani 1 1 d . . .
C20 C 0.52130(17) 0.11612(12) 0.0412(3) 0.0148(5) Uani 1 1 d . . .
H20 H 0.5115 0.1516 -0.0291 0.018 Uiso 1 1 calc R . .
C21 C 0.58159(15) 0.14127(13) 0.1628(3) 0.0155(5) Uani 1 1 d . . .
C22 C 0.58769(19) 0.20551(13) 0.1893(3) 0.0222(6) Uani 1 1 d . . .
H22 H 0.5552 0.2345 0.1303 0.027 Uiso 1 1 calc R . .
C23 C 0.6411(2) 0.22772(15) 0.3019(3) 0.0300(7) Uani 1 1 d . . .
H23 H 0.6448 0.2720 0.3196 0.036 Uiso 1 1 calc R . .
C24 C 0.6891(2) 0.18635(15) 0.3886(3) 0.0272(7) Uani 1 1 d . . .
H24 H 0.7259 0.2018 0.4653 0.033 Uiso 1 1 calc R . .
C25 C 0.6828(2) 0.12243(15) 0.3623(3) 0.0267(7) Uani 1 1 d . . .
H25 H 0.7154 0.0936 0.4216 0.032 Uiso 1 1 calc R . .
C26 C 0.62956(15) 0.09968(12) 0.2505(3) 0.0220(5) Uani 1 1 d . . .
H26 H 0.6258 0.0554 0.2336 0.026 Uiso 1 1 calc R . .
C27 C 0.08391(17) 0.09639(13) 0.4035(3) 0.0147(5) Uani 1 1 d . . .
C28 C -0.00459(17) 0.11953(12) 0.4681(3) 0.0163(5) Uani 1 1 d . . .
H28 H 0.0110 0.1489 0.5495 0.020 Uiso 1 1 calc R . .
C29 C -0.05290(17) 0.15850(13) 0.3533(3) 0.0175(5) Uani 1 1 d . . .
C30 C -0.08823(19) 0.12925(15) 0.2314(3) 0.0330(7) Uani 1 1 d . . .
H30 H -0.0845 0.0845 0.2214 0.040 Uiso 1 1 calc R . .
C31 C -0.1287(3) 0.16495(18) 0.1246(4) 0.0432(9) Uani 1 1 d . . .
H31 H -0.1530 0.1446 0.0413 0.052 Uiso 1 1 calc R . .
C32 C -0.1345(2) 0.23000(17) 0.1369(4) 0.0371(8) Uani 1 1 d . . .
H32 H -0.1620 0.2543 0.0621 0.044 Uiso 1 1 calc R . .
C33 C -0.10026(17) 0.25922(13) 0.2581(4) 0.0292(6) Uani 1 1 d . . .
H33 H -0.1044 0.3039 0.2681 0.035 Uiso 1 1 calc R . .
C34 C -0.05965(19) 0.22340(13) 0.3659(3) 0.0229(6) Uani 1 1 d . . .
H34 H -0.0361 0.2438 0.4497 0.028 Uiso 1 1 calc R . .
H3A H 0.565(2) 0.0392(16) 0.011(3) 0.021(9) Uiso 1 1 d . . .
H6A H -0.058(2) 0.0409(19) 0.477(4) 0.038(11) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 C1 2.094(2) . ?
Sb1 C7 2.103(2) . ?
Sb1 O4 2.1036(16) . ?
Sb1 O1 2.1077(17) . ?
Sb1 C13 2.112(2) . ?
Sb1 O2 3.1512(18) . ?
Sb1 O5 3.3139(18) . ?
O1 C19 1.303(3) . ?
O2 C19 1.219(3) . ?
O3 C20 1.406(3) . ?
O4 C27 1.303(3) . ?
O5 C27 1.220(3) . ?
O6 C28 1.406(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.380(4) . ?
C4 C5 1.382(3) . ?
C5 C6 1.386(3) . ?
C7 C8 1.385(4) . ?
C7 C12 1.386(4) . ?
C8 C9 1.387(4) . ?
C9 C10 1.364(5) . ?
C10 C11 1.369(5) . ?
C11 C12 1.385(4) . ?
C13 C14 1.389(4) . ?
C13 C18 1.389(4) . ?
C14 C15 1.381(4) . ?
C15 C16 1.373(4) . ?
C16 C17 1.378(4) . ?
C17 C18 1.385(4) . ?
C19 C20 1.529(4) . ?
C20 C21 1.528(3) . ?
C21 C22 1.381(4) . ?
C21 C26 1.389(4) . ?
C22 C23 1.386(4) . ?
C23 C24 1.380(4) . ?
C24 C25 1.374(4) . ?
C25 C26 1.383(4) . ?
C27 C28 1.520(4) . ?
C28 C29 1.519(4) . ?
C29 C34 1.379(4) . ?
C29 C30 1.384(4) . ?
C30 C31 1.377(4) . ?
C31 C32 1.381(5) . ?
C32 C33 1.373(5) . ?
C33 C34 1.385(4) . ?

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
C1 Sb1 C7 111.94(9) . . ?
C1 Sb1 O4 85.00(8) . . ?
C7 Sb1 O4 92.06(8) . . ?
C1 Sb1 O1 84.86(7) . . ?
C7 Sb1 O1 93.23(8) . . ?
O4 Sb1 O1 169.73(7) . . ?
C1 Sb1 C13 116.11(9) . . ?
C7 Sb1 C13 131.94(10) . . ?
O4 Sb1 C13 91.28(9) . . ?
O1 Sb1 C13 91.72(8) . . ?
C1 Sb1 O2 129.44(7) . . ?
C7 Sb1 O2 73.42(8) . . ?
O4 Sb1 O2 145.40(6) . . ?
O1 Sb1 O2 44.85(6) . . ?
C13 Sb1 O2 77.09(8) . . ?
C1 Sb1 O5 125.36(7) . . ?
C7 Sb1 O5 69.04(8) . . ?
O4 Sb1 O5 41.66(6) . . ?
O1 Sb1 O5 148.57(6) . . ?
C13 Sb1 O5 82.65(8) . . ?
O2 Sb1 O5 103.99(5) . . ?
C19 O1 Sb1 120.17(16) . . ?
C19 O2 Sb1 70.87(15) . . ?
C27 O4 Sb1 125.92(17) . . ?
C27 O5 Sb1 67.20(14) . . ?
C2 C1 C6 120.2(2) . . ?
C2 C1 Sb1 119.66(16) . . ?
C6 C1 Sb1 120.13(15) . . ?
C3 C2 C1 119.5(2) . . ?
C4 C3 C2 120.3(2) . . ?
C3 C4 C5 120.2(2) . . ?
C4 C5 C6 120.2(2) . . ?
C5 C6 C1 119.5(2) . . ?
C8 C7 C12 120.2(3) . . ?
C8 C7 Sb1 116.4(2) . . ?
C12 C7 Sb1 123.4(2) . . ?
C7 C8 C9 119.1(3) . . ?
C10 C9 C8 121.0(3) . . ?
C9 C10 C11 119.6(3) . . ?
C10 C11 C12 121.0(3) . . ?
C11 C12 C7 119.1(3) . . ?
C14 C13 C18 120.0(2) . . ?
C14 C13 Sb1 119.06(19) . . ?
C18 C13 Sb1 120.70(19) . . ?
C15 C14 C13 119.2(3) . . ?
C16 C15 C14 121.0(3) . . ?
C15 C16 C17 120.0(3) . . ?
C16 C17 C18 120.1(3) . . ?
C17 C18 C13 119.8(3) . . ?
O2 C19 O1 123.9(2) . . ?
O2 C19 C20 123.2(2) . . ?
O1 C19 C20 112.9(2) . . ?
O3 C20 C21 113.5(2) . . ?
O3 C20 C19 112.1(2) . . ?
C21 C20 C19 108.7(2) . . ?
C22 C21 C26 119.0(2) . . ?
C22 C21 C20 120.6(2) . . ?
C26 C21 C20 120.4(2) . . ?
C21 C22 C23 120.1(3) . . ?
C24 C23 C22 120.8(3) . . ?
C25 C24 C23 119.0(3) . . ?
C24 C25 C26 120.7(3) . . ?
C25 C26 C21 120.4(2) . . ?
O5 C27 O4 124.6(2) . . ?
O5 C27 C28 123.1(2) . . ?
O4 C27 C28 112.3(2) . . ?
O6 C28 C29 115.0(2) . . ?
O6 C28 C27 112.2(2) . . ?
C29 C28 C27 108.0(2) . . ?
C34 C29 C30 119.0(3) . . ?
C34 C29 C28 120.9(2) . . ?
C30 C29 C28 120.1(2) . . ?
C31 C30 C29 120.0(3) . . ?
C30 C31 C32 120.9(3) . . ?
C33 C32 C31 119.4(3) . . ?
C32 C33 C34 119.9(3) . . ?
C29 C34 C33 120.9(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O2 0.71(3) 2.08(3) 2.777(3) 169(4) 2_655
O6 H6A O5 0.77(4) 2.06(4) 2.800(3) 163(4) 2

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.078
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vb212reb
_database_code_depnum_ccdc_archive 'CCDC 1578597'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT04171C 2017
_audit_update_record             
;
2017-10-07 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;
_audit_creation_date             2017-10-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        trisphenylbismuth-bis(R-mandelate)
_chemical_formula_moiety         'C34 H29 Bi O6'
_chemical_formula_sum            'C34 H29 Bi O6'
_chemical_formula_weight         742.55
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.2480(8)
_cell_length_b                   12.0087(11)
_cell_length_c                   23.2139(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2856.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4298
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.66
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.385
_shelx_estimated_absorpt_T_min   0.213
_exptl_absorpt_coefficient_mu    6.217
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.1081 before and 0.0727 after correction. The Ratio of minimum to maximum transmission is 0.6493. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23841
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.808
_diffrn_reflns_theta_min         2.440
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                7068
_reflns_number_total             8078
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.918
_refine_diff_density_min         -1.306
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details 
;
 Flack x determined using 2807 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         8078
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      0.890
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0632
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20), C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C6(H6A), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Bi1 Bi 0.37858(2) 0.71234(2) 0.21025(2) 0.01103(6) Uani 1 1 d . . . . .
O1 O 0.3407(4) 0.5843(4) 0.28109(18) 0.0131(10) Uani 1 1 d . . . . .
O2 O 0.1324(5) 0.6045(4) 0.25740(17) 0.0188(10) Uani 1 1 d . . . . .
O3 O 0.0455(5) 0.5070(5) 0.3518(2) 0.0267(13) Uani 1 1 d . . . . .
H3 H 0.009363 0.532615 0.322173 0.032 Uiso 1 1 calc GR . . . .
O4 O 0.4260(4) 0.8488(4) 0.14219(18) 0.0166(10) Uani 1 1 d . . . . .
O5 O 0.2101(4) 0.8275(4) 0.13592(18) 0.0163(10) Uani 1 1 d . . . . .
O6 O 0.1828(5) 1.0018(5) 0.0658(2) 0.0238(12) Uani 1 1 d . . . . .
H6 H 0.132356 0.970868 0.089439 0.029 Uiso 1 1 calc GR . . . .
C1 C 0.5841(5) 0.7133(6) 0.2376(2) 0.0134(11) Uani 1 1 d . . . . .
C2 C 0.6722(5) 0.7861(6) 0.2118(3) 0.0174(11) Uani 1 1 d . . . . .
H2 H 0.644187 0.833810 0.181561 0.021 Uiso 1 1 calc R . . . .
C3 C 0.7998(6) 0.7887(7) 0.2301(3) 0.0198(13) Uani 1 1 d . . . . .
H3A H 0.860191 0.837440 0.212013 0.024 Uiso 1 1 calc R . . . .
C4 C 0.8409(6) 0.7207(6) 0.2748(3) 0.0202(14) Uani 1 1 d . . . . .
H4 H 0.929190 0.722833 0.287246 0.024 Uiso 1 1 calc R . . . .
C5 C 0.7528(7) 0.6493(7) 0.3013(3) 0.0256(16) Uani 1 1 d . . . . .
H5 H 0.780285 0.604618 0.332845 0.031 Uiso 1 1 calc R . . . .
C6 C 0.6248(7) 0.6430(6) 0.2821(3) 0.0225(13) Uani 1 1 d . . . . .
H6A H 0.565634 0.591510 0.298921 0.027 Uiso 1 1 calc R . . . .
C7 C 0.2836(6) 0.8372(5) 0.2657(3) 0.0135(12) Uani 1 1 d . . . . .
C8 C 0.3640(7) 0.8828(6) 0.3072(2) 0.0186(14) Uani 1 1 d . . . . .
H8 H 0.452409 0.859984 0.310636 0.022 Uiso 1 1 calc R . . . .
C9 C 0.3124(8) 0.9628(7) 0.3437(3) 0.0275(18) Uani 1 1 d . . . . .
H9 H 0.365803 0.996173 0.372378 0.033 Uiso 1 1 calc R . . . .
C10 C 0.1844(8) 0.9938(6) 0.3384(3) 0.0245(17) Uani 1 1 d . . . . .
H10 H 0.149425 1.048347 0.363658 0.029 Uiso 1 1 calc R . . . .
C11 C 0.1045(7) 0.9463(6) 0.2964(3) 0.0251(15) Uani 1 1 d . . . . .
H11 H 0.015661 0.968168 0.293269 0.030 Uiso 1 1 calc R . . . .
C12 C 0.1550(6) 0.8674(6) 0.2593(3) 0.0184(14) Uani 1 1 d . . . . .
H12 H 0.102337 0.834770 0.230209 0.022 Uiso 1 1 calc R . . . .
C13 C 0.3499(6) 0.5907(6) 0.1398(3) 0.0163(14) Uani 1 1 d . . . . .
C14 C 0.4067(7) 0.6145(6) 0.0879(3) 0.0202(15) Uani 1 1 d . . . . .
H14 H 0.453325 0.682056 0.082292 0.024 Uiso 1 1 calc R . . . .
C15 C 0.3946(8) 0.5373(6) 0.0435(3) 0.0257(17) Uani 1 1 d . . . . .
H15 H 0.432702 0.552438 0.006983 0.031 Uiso 1 1 calc R . . . .
C16 C 0.3279(8) 0.4394(7) 0.0520(3) 0.0283(18) Uani 1 1 d . . . . .
H16 H 0.320741 0.387022 0.021472 0.034 Uiso 1 1 calc R . . . .
C17 C 0.2702(9) 0.4163(7) 0.1056(3) 0.0309(19) Uani 1 1 d . . . . .
H17 H 0.223619 0.348784 0.111292 0.037 Uiso 1 1 calc R . . . .
C18 C 0.2817(8) 0.4927(7) 0.1503(3) 0.0252(16) Uani 1 1 d . . . . .
H18 H 0.244114 0.478354 0.186963 0.030 Uiso 1 1 calc R . . . .
C19 C 0.2190(5) 0.5769(5) 0.2915(3) 0.0120(11) Uani 1 1 d . . . . .
C20 C 0.1782(7) 0.5372(6) 0.3519(3) 0.0174(14) Uani 1 1 d . . . . .
H20 H 0.231387 0.470263 0.362249 0.021 Uiso 1 1 calc R . . . .
C21 C 0.2105(7) 0.6300(6) 0.3936(3) 0.0191(14) Uani 1 1 d . . . . .
C22 C 0.3388(8) 0.6433(8) 0.4119(3) 0.0292(18) Uani 1 1 d . . . . .
H22 H 0.403838 0.591721 0.400204 0.035 Uiso 1 1 calc R . . . .
C23 C 0.3715(12) 0.7318(8) 0.4473(3) 0.048(3) Uani 1 1 d . . . . .
H23 H 0.458961 0.741134 0.460038 0.058 Uiso 1 1 calc R . . . .
C24 C 0.2759(14) 0.8069(9) 0.4640(4) 0.059(4) Uani 1 1 d . . . . .
H24 H 0.298227 0.867512 0.488347 0.070 Uiso 1 1 calc R . . . .
C25 C 0.1498(12) 0.7946(8) 0.4458(3) 0.047(3) Uani 1 1 d . . . . .
H25 H 0.085284 0.846771 0.457503 0.057 Uiso 1 1 calc R . . . .
C26 C 0.1156(9) 0.7060(6) 0.4103(3) 0.0274(15) Uani 1 1 d . . . . .
H26 H 0.028044 0.697527 0.397629 0.033 Uiso 1 1 calc R . . . .
C27 C 0.3122(7) 0.8713(6) 0.1206(3) 0.0162(14) Uani 1 1 d . . . . .
C28 C 0.3092(7) 0.9568(6) 0.0717(3) 0.0163(14) Uani 1 1 d . . . . .
H28 H 0.372135 1.018090 0.080447 0.020 Uiso 1 1 calc R . . . .
C29 C 0.3529(7) 0.8964(6) 0.0174(3) 0.0170(14) Uani 1 1 d . . . . .
C30 C 0.2647(8) 0.8290(6) -0.0124(3) 0.0219(15) Uani 1 1 d . . . . .
H30 H 0.175944 0.826351 -0.000639 0.026 Uiso 1 1 calc R . . . .
C31 C 0.3056(8) 0.7664(7) -0.0588(3) 0.0283(18) Uani 1 1 d . . . . .
H31 H 0.245454 0.719822 -0.078536 0.034 Uiso 1 1 calc R . . . .
C32 C 0.4357(8) 0.7714(7) -0.0767(3) 0.0288(19) Uani 1 1 d . . . . .
H32 H 0.464415 0.727301 -0.108239 0.035 Uiso 1 1 calc R . . . .
C33 C 0.5219(7) 0.8399(7) -0.0488(3) 0.0257(17) Uani 1 1 d . . . . .
H33 H 0.609764 0.844767 -0.061522 0.031 Uiso 1 1 calc R . . . .
C34 C 0.4811(7) 0.9018(7) -0.0022(3) 0.0232(16) Uani 1 1 d . . . . .
H34 H 0.541553 0.949058 0.016878 0.028 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O1 2.284(4) . ?
Bi1 O2 3.040(5) . ?
Bi1 O4 2.327(5) . ?
Bi1 O5 2.806(4) . ?
Bi1 C1 2.200(6) . ?
Bi1 C7 2.203(6) . ?
Bi1 C13 2.213(7) . ?
O1 C19 1.274(7) . ?
O2 C19 1.234(8) . ?
O3 C20 1.408(8) . ?
O4 C27 1.297(8) . ?
O5 C27 1.224(8) . ?
O6 C28 1.410(9) . ?
C1 C2 1.392(9) . ?
C1 C6 1.397(9) . ?
C2 C3 1.376(8) . ?
C3 C4 1.386(9) . ?
C4 C5 1.389(10) . ?
C5 C6 1.388(10) . ?
C7 C8 1.381(9) . ?
C7 C12 1.375(9) . ?
C8 C9 1.386(10) . ?
C9 C10 1.369(12) . ?
C10 C11 1.395(11) . ?
C11 C12 1.380(10) . ?
C13 C14 1.368(9) . ?
C13 C18 1.390(10) . ?
C14 C15 1.392(9) . ?
C15 C16 1.375(11) . ?
C16 C17 1.406(11) . ?
C17 C18 1.390(10) . ?
C19 C20 1.540(9) . ?
C20 C21 1.513(10) . ?
C21 C22 1.391(10) . ?
C21 C26 1.389(10) . ?
C22 C23 1.384(12) . ?
C23 C24 1.387(16) . ?
C24 C25 1.367(16) . ?
C25 C26 1.390(12) . ?
C27 C28 1.531(9) . ?
C28 C29 1.521(9) . ?
C29 C30 1.397(10) . ?
C29 C34 1.392(10) . ?
C30 C31 1.379(10) . ?
C31 C32 1.398(11) . ?
C32 C33 1.370(12) . ?
C33 C34 1.376(10) . ?

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 Bi1 O2 46.62(14) . . ?
O1 Bi1 O4 176.31(16) . . ?
O1 Bi1 O5 132.06(14) . . ?
O4 Bi1 O2 135.85(14) . . ?
O4 Bi1 O5 50.50(14) . . ?
O5 Bi1 O2 85.44(13) . . ?
C1 Bi1 O1 87.6(2) . . ?
C1 Bi1 O2 133.85(19) . . ?
C1 Bi1 O4 89.6(2) . . ?
C1 Bi1 O5 139.8(2) . . ?
C1 Bi1 C7 104.5(2) . . ?
C1 Bi1 C13 110.1(2) . . ?
C7 Bi1 O1 87.8(2) . . ?
C7 Bi1 O2 73.30(19) . . ?
C7 Bi1 O4 90.6(2) . . ?
C7 Bi1 O5 75.65(19) . . ?
C7 Bi1 C13 145.3(2) . . ?
C13 Bi1 O1 93.75(19) . . ?
C13 Bi1 O2 82.80(19) . . ?
C13 Bi1 O4 89.5(2) . . ?
C13 Bi1 O5 77.8(2) . . ?
C19 O1 Bi1 110.5(4) . . ?
C19 O2 Bi1 75.4(4) . . ?
C27 O4 Bi1 102.8(4) . . ?
C27 O5 Bi1 82.2(4) . . ?
C2 C1 Bi1 119.9(4) . . ?
C2 C1 C6 120.3(6) . . ?
C6 C1 Bi1 119.7(5) . . ?
C3 C2 C1 119.8(6) . . ?
C2 C3 C4 120.5(6) . . ?
C3 C4 C5 119.9(6) . . ?
C6 C5 C4 120.4(6) . . ?
C5 C6 C1 119.1(6) . . ?
C8 C7 Bi1 114.5(5) . . ?
C12 C7 Bi1 122.7(5) . . ?
C12 C7 C8 122.8(6) . . ?
C7 C8 C9 118.3(7) . . ?
C10 C9 C8 119.9(7) . . ?
C9 C10 C11 121.0(7) . . ?
C12 C11 C10 119.7(7) . . ?
C7 C12 C11 118.3(6) . . ?
C14 C13 Bi1 117.1(5) . . ?
C14 C13 C18 123.1(6) . . ?
C18 C13 Bi1 119.7(5) . . ?
C13 C14 C15 118.3(7) . . ?
C16 C15 C14 120.5(6) . . ?
C15 C16 C17 120.4(7) . . ?
C18 C17 C16 119.7(7) . . ?
C17 C18 C13 118.1(7) . . ?
O1 C19 C20 117.4(6) . . ?
O2 C19 O1 124.3(6) . . ?
O2 C19 C20 118.2(5) . . ?
O3 C20 C19 109.9(6) . . ?
O3 C20 C21 113.7(6) . . ?
C21 C20 C19 107.2(5) . . ?
C22 C21 C20 119.1(7) . . ?
C26 C21 C20 120.6(7) . . ?
C26 C21 C22 120.1(7) . . ?
C23 C22 C21 119.9(9) . . ?
C22 C23 C24 119.6(10) . . ?
C25 C24 C23 120.8(9) . . ?
C24 C25 C26 120.2(9) . . ?
C21 C26 C25 119.5(9) . . ?
O4 C27 C28 116.4(6) . . ?
O5 C27 O4 124.5(6) . . ?
O5 C27 C28 119.1(6) . . ?
O6 C28 C27 110.3(5) . . ?
O6 C28 C29 112.0(5) . . ?
C29 C28 C27 106.8(6) . . ?
C30 C29 C28 119.7(6) . . ?
C34 C29 C28 121.8(6) . . ?
C34 C29 C30 118.4(6) . . ?
C31 C30 C29 120.4(7) . . ?
C30 C31 C32 119.9(8) . . ?
C33 C32 C31 120.0(7) . . ?
C32 C33 C34 120.0(7) . . ?
C33 C34 C29 121.2(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.84 2.14 2.640(7) 117.6 .
O6 H6 O5 0.84 2.18 2.666(7) 116.5 .

_olex2_submission_special_instructions 'No special instructions were received'
