# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_biphdppa
_database_code_depnum_ccdc_archive 'CCDC 1943307'
loop_
_audit_author_name
_audit_author_address
'Megan Herdman'
;Monash University
Australia
;
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;
_audit_creation_date             2019-02-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        'Diphenyl bismuth mono-diphenylphosphinate'
_chemical_formula_moiety         'C24 H20 Bi O2 P'
_chemical_formula_sum            'C24 H20 Bi O2 P'
_chemical_formula_weight         580.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Bi1 C20 H20 P1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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_
# start Validation Reply Form
_vrf_PLAT971_biphdppa
;
PROBLEM: Check Calcd Resid. Dens.  1.14A   From Bi1             2.95 eA-3  
RESPONSE: The residual density is due to the heavy atom (Bi) 
and absorption corrections were applied with minimal change to 
the structure. All other analytical data is in agreeance with 
the obtained structure.
;
# end Validation Reply Form
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                   9.9875(5)
_cell_length_b                   11.0201(4)
_cell_length_c                   19.3941(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2134.58(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4662
_cell_measurement_temperature    123.01(12)
_cell_measurement_theta_max      66.9270
_cell_measurement_theta_min      5.9880
_shelx_estimated_absorpt_T_max   0.234
_shelx_estimated_absorpt_T_min   0.149
_exptl_absorpt_coefficient_mu    17.045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7878
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        66.951
_diffrn_reflns_theta_max         66.951
_diffrn_reflns_theta_min         4.560
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  44.00   1.00    2.00    --   41.27  38.00  30.00   27
  2  ω     81.00 116.00   1.00    2.00    --   41.27  38.00  30.00   35
  3  ω     58.00 104.00   1.00    4.00    --   92.50 -30.00 -30.00   46
  4  ω     59.00  84.00   1.00    4.00    --   92.50 -95.00 -30.00   25
  5  ω     61.00  95.00   1.00    4.00    --   92.50-126.00   0.00   34
  6  ω     53.00  96.00   1.00    4.00    --   92.50-126.00 -60.00   43
  7  ω     32.00  88.00   1.00    2.00    --   41.27-126.00-120.00   56
  8  ω     34.00  81.00   1.00    4.00    --   92.50 -95.00-120.00   47
  9  ω     11.00  37.00   1.00    4.00    --   92.50 -95.00 -30.00   26
 10  ω     35.00  66.00   1.00    4.00    --   92.50-126.00  30.00   31
 11  ω     79.00 116.00   1.00    4.00    --   92.50 -45.00 120.00   37
 12  ω     65.00 169.00   1.00    4.00    --   92.50  30.00 150.00  104
 13  ω     29.00  55.00   1.00    4.00    --   92.50 -45.00 120.00   26
 14  ω     -1.00  24.00   1.00    2.00    --   41.27-126.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0656245000
_diffrn_orient_matrix_UB_12      0.0440380000
_diffrn_orient_matrix_UB_13      -0.0674194000
_diffrn_orient_matrix_UB_21      -0.1390910000
_diffrn_orient_matrix_UB_22      -0.0314964000
_diffrn_orient_matrix_UB_23      0.0292456000
_diffrn_orient_matrix_UB_31      -0.0116289000
_diffrn_orient_matrix_UB_32      0.1288884000
_diffrn_orient_matrix_UB_33      0.0301691000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.865
_reflns_Friedel_fraction_max     0.865
_reflns_number_gt                3495
_reflns_number_total             3565
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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         3.012
_refine_diff_density_min         -1.272
_refine_diff_density_rms         0.167
_refine_ls_abs_structure_details 
;
 Flack x determined using 1342 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.043(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.033
_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)+(0.0470P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0735
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C3(H3), C21(H21), C17(H17), C20(H20), C12(H12), C8(H8), C2(H2),
 C18(H18), C15(H15), C24(H24), C5(H5), C11(H11), C22(H22), C23(H23), C4(H4),
 C9(H9), C16(H16), C10(H10), C6(H6)
;
_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
Bi1 Bi 0.72155(3) 0.72433(2) 0.49005(2) 0.01339(12) Uani 1 1 d . . . . .
P1 P 0.4474(2) 0.50901(17) 0.47777(11) 0.0138(4) Uani 1 1 d . . . . .
O1 O 0.5878(6) 0.5555(5) 0.4697(3) 0.0192(14) Uani 1 1 d . . . . .
O2 O 0.3439(6) 0.5944(5) 0.5063(3) 0.0202(13) Uani 1 1 d . . . . .
C14 C 0.4438(10) 0.3472(8) 0.3674(5) 0.0194(19) Uani 1 1 d . . . . .
H14 H 0.502506 0.300510 0.393520 0.023 Uiso 1 1 calc R . . . .
C3 C 0.9878(11) 0.7242(11) 0.3016(5) 0.031(2) Uani 1 1 d . . . . .
H3 H 1.063098 0.767515 0.287776 0.037 Uiso 1 1 calc R . . . .
C21 C 0.5824(9) 0.2182(9) 0.5873(4) 0.0203(19) Uani 1 1 d . . . . .
H21 H 0.663743 0.179054 0.594523 0.024 Uiso 1 1 calc R . . . .
C13 C 0.3944(9) 0.4560(7) 0.3940(5) 0.0147(17) Uani 1 1 d . . . . .
C17 C 0.2689(12) 0.4848(9) 0.2895(5) 0.028(2) Uani 1 1 d . . . . .
H17 H 0.210257 0.531157 0.263139 0.033 Uiso 1 1 calc R . . . .
C20 C 0.5766(9) 0.3197(7) 0.5443(5) 0.0169(18) Uani 1 1 d . . . . .
H20 H 0.653714 0.348308 0.522867 0.020 Uiso 1 1 calc R . . . .
C12 C 0.5283(10) 0.9513(8) 0.4759(5) 0.021(2) Uani 1 1 d . . . . .
H12 H 0.571128 0.973030 0.516630 0.026 Uiso 1 1 calc R . . . .
C8 C 0.4946(10) 0.8121(8) 0.3822(5) 0.0184(19) Uani 1 1 d . . . . .
H8 H 0.514009 0.739055 0.360406 0.022 Uiso 1 1 calc R . . . .
C2 C 0.9281(11) 0.7496(8) 0.3655(5) 0.024(2) Uani 1 1 d . . . . .
H2 H 0.963359 0.810406 0.393281 0.029 Uiso 1 1 calc R . . . .
C18 C 0.3062(10) 0.5240(9) 0.3543(5) 0.022(2) Uani 1 1 d . . . . .
H18 H 0.272083 0.596517 0.371466 0.027 Uiso 1 1 calc R . . . .
C15 C 0.4061(10) 0.3081(9) 0.3023(5) 0.026(2) Uani 1 1 d . . . . .
H15 H 0.439905 0.235816 0.284723 0.031 Uiso 1 1 calc R . . . .
C1 C 0.8163(9) 0.6845(7) 0.3877(4) 0.0133(17) Uani 1 1 d . . . . .
C24 C 0.3395(9) 0.3352(8) 0.5663(5) 0.0197(18) Uani 1 1 d . . . . .
H24 H 0.258277 0.375015 0.559953 0.024 Uiso 1 1 calc R . . . .
C7 C 0.5605(9) 0.8421(8) 0.4436(4) 0.0163(17) Uani 1 1 d . . . . .
C5 C 0.8241(11) 0.5718(9) 0.2809(5) 0.026(2) Uani 1 1 d . . . . .
H5 H 0.787097 0.513094 0.252168 0.031 Uiso 1 1 calc R . . . .
C11 C 0.4320(10) 1.0280(8) 0.4472(5) 0.024(2) Uani 1 1 d . . . . .
H11 H 0.410442 1.100200 0.469419 0.029 Uiso 1 1 calc R . . . .
C22 C 0.4675(11) 0.1753(9) 0.6193(5) 0.025(2) Uani 1 1 d . . . . .
H22 H 0.471798 0.107828 0.648000 0.030 Uiso 1 1 calc R . . . .
C19 C 0.4545(9) 0.3777(7) 0.5338(4) 0.0142(16) Uani 1 1 d . . . . .
C23 C 0.3461(10) 0.2333(9) 0.6083(5) 0.027(2) Uani 1 1 d . . . . .
H23 H 0.268832 0.203881 0.629199 0.032 Uiso 1 1 calc R . . . .
C4 C 0.9359(10) 0.6356(9) 0.2591(5) 0.027(2) Uani 1 1 d . . . . .
H4 H 0.975109 0.619073 0.216607 0.032 Uiso 1 1 calc R . . . .
C9 C 0.4017(10) 0.8891(8) 0.3539(5) 0.022(2) Uani 1 1 d . . . . .
H9 H 0.360325 0.868438 0.312546 0.027 Uiso 1 1 calc R . . . .
C16 C 0.3182(10) 0.3768(10) 0.2636(5) 0.029(2) Uani 1 1 d . . . . .
H16 H 0.292239 0.350387 0.220038 0.034 Uiso 1 1 calc R . . . .
C10 C 0.3684(10) 0.9981(9) 0.3863(5) 0.024(2) Uani 1 1 d . . . . .
H10 H 0.304615 1.049581 0.367274 0.029 Uiso 1 1 calc R . . . .
C6 C 0.7665(11) 0.5939(8) 0.3446(5) 0.0209(19) Uani 1 1 d . . . . .
H6 H 0.693641 0.547644 0.358898 0.025 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 2.324(6) . ?
Bi1 O2 2.342(5) 4_566 ?
Bi1 C1 2.243(8) . ?
Bi1 C7 2.254(9) . ?
P1 O1 1.501(6) . ?
P1 O2 1.504(6) . ?
P1 C13 1.805(9) . ?
P1 C19 1.811(8) . ?
C14 H14 0.9300 . ?
C14 C13 1.396(13) . ?
C14 C15 1.386(13) . ?
C3 H3 0.9300 . ?
C3 C2 1.403(13) . ?
C3 C4 1.379(15) . ?
C21 H21 0.9300 . ?
C21 C20 1.397(13) . ?
C21 C22 1.388(14) . ?
C13 C18 1.390(13) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(14) . ?
C17 C16 1.383(15) . ?
C20 H20 0.9300 . ?
C20 C19 1.392(12) . ?
C12 H12 0.9300 . ?
C12 C7 1.394(12) . ?
C12 C11 1.396(14) . ?
C8 H8 0.9300 . ?
C8 C7 1.399(13) . ?
C8 C9 1.373(13) . ?
C2 H2 0.9300 . ?
C2 C1 1.395(13) . ?
C18 H18 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.381(14) . ?
C1 C6 1.394(12) . ?
C24 H24 0.9300 . ?
C24 C19 1.392(13) . ?
C24 C23 1.389(13) . ?
C5 H5 0.9300 . ?
C5 C4 1.385(15) . ?
C5 C6 1.386(13) . ?
C11 H11 0.9300 . ?
C11 C10 1.381(15) . ?
C22 H22 0.9300 . ?
C22 C23 1.387(15) . ?
C23 H23 0.9300 . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.395(14) . ?
C16 H16 0.9300 . ?
C10 H10 0.9300 . ?
C6 H6 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
O1 Bi1 O2 170.9(2) . 4_566 ?
C1 Bi1 O1 86.3(3) . . ?
C1 Bi1 O2 88.5(3) . 4_566 ?
C1 Bi1 C7 93.4(3) . . ?
C7 Bi1 O1 89.0(3) . . ?
C7 Bi1 O2 83.9(3) . 4_566 ?
O1 P1 O2 117.8(3) . . ?
O1 P1 C13 106.9(4) . . ?
O1 P1 C19 107.4(4) . . ?
O2 P1 C13 109.4(4) . . ?
O2 P1 C19 107.8(4) . . ?
C13 P1 C19 107.0(4) . . ?
P1 O1 Bi1 142.4(4) . . ?
P1 O2 Bi1 154.6(4) . 4_466 ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C15 C14 C13 120.5(9) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.6(9) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C22 C21 C20 120.3(8) . . ?
C14 C13 P1 120.5(7) . . ?
C18 C13 P1 120.7(7) . . ?
C18 C13 C14 118.8(9) . . ?
C18 C17 H17 119.9 . . ?
C18 C17 C16 120.3(10) . . ?
C16 C17 H17 119.9 . . ?
C21 C20 H20 120.3 . . ?
C19 C20 C21 119.4(8) . . ?
C19 C20 H20 120.3 . . ?
C7 C12 H12 119.9 . . ?
C7 C12 C11 120.2(8) . . ?
C11 C12 H12 119.9 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C9 C8 C7 120.9(8) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 C3 120.7(9) . . ?
C1 C2 H2 119.6 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.5(9) . . ?
C17 C18 H18 119.8 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.9(9) . . ?
C16 C15 H15 120.1 . . ?
C2 C1 Bi1 120.7(6) . . ?
C6 C1 Bi1 121.3(6) . . ?
C6 C1 C2 118.0(8) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C19 119.9(9) . . ?
C12 C7 Bi1 118.8(6) . . ?
C12 C7 C8 118.5(8) . . ?
C8 C7 Bi1 122.7(6) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(9) . . ?
C6 C5 H5 119.4 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.8(9) . . ?
C10 C11 H11 119.6 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.8(8) . . ?
C23 C22 H22 120.1 . . ?
C20 C19 P1 119.3(7) . . ?
C20 C19 C24 120.2(7) . . ?
C24 C19 P1 120.5(7) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.3(9) . . ?
C22 C23 H23 119.8 . . ?
C3 C4 C5 118.7(9) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(9) . . ?
C10 C9 H9 119.6 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0(9) . . ?
C15 C16 H16 120.0 . . ?
C11 C10 C9 118.8(9) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.8(9) . . ?
C5 C6 H6 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.482
_oxdiff_exptl_absorpt_empirical_full_min 0.676
####################################################################### 
# 
# 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_test2
_database_code_depnum_ccdc_archive 'CCDC 1943310'
loop_
_audit_author_name
_audit_author_address
'Megan Herdman'
;Monash University
Australia
;
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;
_audit_creation_date             2019-02-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        'diphenyl bismuth mono-phenylphosphinate'
_chemical_formula_moiety         'C18 H16 Bi O2 P'
_chemical_formula_sum            'C18 H16 Bi O2 P'
_chemical_formula_weight         504.26
_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'
P P 0.1023 0.0942 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.5068(11)
_cell_length_b                   8.9144(6)
_cell_length_c                   21.9738(18)
_cell_angle_alpha                90
_cell_angle_beta                 112.186(4)
_cell_angle_gamma                90
_cell_volume                     3356.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3802
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      26.59
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.484
_shelx_estimated_absorpt_T_min   0.266
_exptl_absorpt_coefficient_mu    10.604
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1137 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.5709.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14755
_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         27.484
_diffrn_reflns_theta_min         2.575
_diffrn_ambient_temperature      123(1)
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3155
_reflns_number_total             3858
_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         1.143
_refine_diff_density_min         -1.104
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3858
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.003
_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)+(0.0221P)²+5.5630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0599
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C17(H17), C18(H18), C14(H14), C4(H4), C5(H5), C3(H3), C9(H9), C2(H2),
 C6(H6), C15(H15), C10(H10), C16(H16), C12(H12), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_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
Bi1 Bi 0.26296(2) 0.32533(2) 0.24317(2) 0.01671(6) Uani 1 1 d . . . . .
P1 P 0.41019(7) 0.05637(13) 0.28577(6) 0.0163(3) Uani 1 1 d . . . . .
O2 O 0.35645(18) -0.0457(4) 0.30279(18) 0.0268(8) Uani 1 1 d . . . . .
O1 O 0.37888(18) 0.2050(3) 0.25427(18) 0.0248(8) Uani 1 1 d . . . . .
C7 C 0.3030(3) 0.4841(5) 0.1829(2) 0.0174(10) Uani 1 1 d . . . . .
C13 C 0.2028(3) 0.1688(5) 0.1587(2) 0.0191(10) Uani 1 1 d . . . . .
C8 C 0.2508(3) 0.5430(5) 0.1250(2) 0.0208(10) Uani 1 1 d . . . . .
H8 H 0.198644 0.514676 0.110185 0.025 Uiso 1 1 calc R . . . .
C17 C 0.2049(3) 0.0107(6) 0.0708(3) 0.0336(13) Uani 1 1 d . . . . .
H17 H 0.231604 -0.028483 0.046134 0.040 Uiso 1 1 calc R . . . .
C18 C 0.2420(3) 0.1084(5) 0.1217(2) 0.0213(11) Uani 1 1 d . . . . .
H18 H 0.293799 0.134128 0.131253 0.026 Uiso 1 1 calc R . . . .
C14 C 0.1257(3) 0.1300(5) 0.1432(3) 0.0229(11) Uani 1 1 d . . . . .
H14 H 0.098218 0.171608 0.166786 0.028 Uiso 1 1 calc R . . . .
C4 C 0.6196(3) 0.1515(6) 0.4748(3) 0.0278(12) Uani 1 1 d . . . . .
H4 H 0.661668 0.172302 0.513551 0.033 Uiso 1 1 calc R . . . .
C5 C 0.5765(3) 0.0220(6) 0.4697(3) 0.0291(12) Uani 1 1 d . . . . .
H5 H 0.589881 -0.044944 0.504724 0.035 Uiso 1 1 calc R . . . .
C3 C 0.6007(3) 0.2495(6) 0.4230(3) 0.0255(12) Uani 1 1 d . . . . .
H3 H 0.629936 0.336257 0.426791 0.031 Uiso 1 1 calc R . . . .
C9 C 0.2747(3) 0.6434(5) 0.0884(3) 0.0266(12) Uani 1 1 d . . . . .
H9 H 0.238761 0.681320 0.049223 0.032 Uiso 1 1 calc R . . . .
C2 C 0.5385(3) 0.2200(5) 0.3652(3) 0.0219(11) Uani 1 1 d . . . . .
H2 H 0.526228 0.286241 0.330016 0.026 Uiso 1 1 calc R . . . .
C6 C 0.5133(3) -0.0070(5) 0.4120(3) 0.0241(11) Uani 1 1 d . . . . .
H6 H 0.483645 -0.093151 0.408697 0.029 Uiso 1 1 calc R . . . .
C15 C 0.0888(3) 0.0295(6) 0.0928(3) 0.0321(13) Uani 1 1 d . . . . .
H15 H 0.037278 0.001676 0.083555 0.038 Uiso 1 1 calc R . . . .
C10 C 0.3518(3) 0.6877(5) 0.1097(3) 0.0285(12) Uani 1 1 d . . . . .
H10 H 0.367829 0.756583 0.085618 0.034 Uiso 1 1 calc R . . . .
C16 C 0.1285(3) -0.0288(6) 0.0566(3) 0.0362(14) Uani 1 1 d . . . . .
H16 H 0.103648 -0.095102 0.022352 0.043 Uiso 1 1 calc R . . . .
C1 C 0.4938(3) 0.0904(5) 0.3596(2) 0.0176(10) Uani 1 1 d . . . . .
C12 C 0.3808(3) 0.5280(5) 0.2036(3) 0.0230(11) Uani 1 1 d . . . . .
H12 H 0.417039 0.488986 0.242375 0.028 Uiso 1 1 calc R . . . .
C11 C 0.4049(3) 0.6282(6) 0.1675(3) 0.0289(12) Uani 1 1 d . . . . .
H11 H 0.457115 0.656067 0.181934 0.035 Uiso 1 1 calc R . . . .
H1 H 0.436(2) -0.021(5) 0.246(2) 0.006(10) 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
Bi1 O2 2.354(3) 4 ?
Bi1 O1 2.328(3) . ?
Bi1 C7 2.246(5) . ?
Bi1 C13 2.251(5) . ?
P1 O2 1.496(3) . ?
P1 O1 1.505(3) . ?
P1 C1 1.795(5) . ?
P1 H1 1.33(4) . ?
C7 C8 1.379(6) . ?
C7 C12 1.393(6) . ?
C13 C18 1.387(7) . ?
C13 C14 1.380(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(7) . ?
C17 C16 1.373(8) . ?
C18 H18 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.387(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(7) . ?
C4 C3 1.371(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.379(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.399(6) . ?
C6 H6 0.9300 . ?
C6 C1 1.378(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(7) . ?
C16 H16 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.376(7) . ?
C11 H11 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
O1 Bi1 O2 161.63(13) . 4 ?
C7 Bi1 O2 84.51(14) . 4 ?
C7 Bi1 O1 81.75(14) . . ?
C7 Bi1 C13 94.33(17) . . ?
C13 Bi1 O2 81.80(14) . 4 ?
C13 Bi1 O1 87.13(15) . . ?
O2 P1 O1 118.2(2) . . ?
O2 P1 C1 107.7(2) . . ?
O2 P1 H1 106.3(17) . . ?
O1 P1 C1 108.5(2) . . ?
O1 P1 H1 109.0(18) . . ?
C1 P1 H1 106.4(16) . . ?
P1 O2 Bi1 142.7(2) . 4_545 ?
P1 O1 Bi1 129.3(2) . . ?
C8 C7 Bi1 120.9(3) . . ?
C8 C7 C12 118.1(5) . . ?
C12 C7 Bi1 121.0(3) . . ?
C18 C13 Bi1 121.3(3) . . ?
C14 C13 Bi1 120.2(4) . . ?
C14 C13 C18 118.5(5) . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(5) . . ?
C9 C8 H8 119.4 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(5) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.7(5) . . ?
C17 C18 H18 119.6 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(5) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(5) . . ?
C6 C5 H5 120.3 . . ?
C4 C3 H3 119.8 . . ?
C4 C3 C2 120.4(5) . . ?
C2 C3 H3 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.3(5) . . ?
C10 C9 H9 119.9 . . ?
C3 C2 H2 120.1 . . ?
C3 C2 C1 119.9(5) . . ?
C1 C2 H2 120.1 . . ?
C5 C6 H6 119.7 . . ?
C1 C6 C5 120.7(5) . . ?
C1 C6 H6 119.7 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(5) . . ?
C16 C15 H15 120.1 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(5) . . ?
C11 C10 H10 120.4 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0(5) . . ?
C15 C16 H16 120.0 . . ?
C2 C1 P1 119.9(4) . . ?
C6 C1 P1 120.9(4) . . ?
C6 C1 C2 119.2(4) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.0(5) . . ?
C11 C12 H12 119.5 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.8 . . ?

_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_biphmppa
_database_code_depnum_ccdc_archive 'CCDC 1943308'
loop_
_audit_author_name
_audit_author_address
'Megan Herdman'
;Monash University
Australia
;
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;
_audit_creation_date             2019-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
'diphenyl bismuth mono-bis-p-methoxyphenylphosphinate'
_chemical_formula_moiety         'C26 H24 Bi O4 P'
_chemical_formula_sum            'C26 H24 Bi O4 P'
_chemical_formula_weight         640.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         Bi(C6H5)(P2O6C14H20)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.0180(3)
_cell_length_b                   10.7673(3)
_cell_length_c                   17.6146(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.874(2)
_cell_angle_gamma                90
_cell_volume                     2271.11(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7322
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      66.8680
_cell_measurement_theta_min      4.2740
_shelx_estimated_absorpt_T_max   0.499
_shelx_estimated_absorpt_T_min   0.324
_exptl_absorpt_coefficient_mu    16.159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15407
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.040
_diffrn_reflns_theta_max         67.040
_diffrn_reflns_theta_min         4.289
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  63.00   1.00    4.00    --   41.46 -77.00  90.00   97
  2  ω     43.00 129.00   1.00   16.00    --   92.50 -92.00  21.13   86
  3  ω     96.00 122.00   1.00   16.00    --   92.50 -93.00  60.02   26
  4  ω    104.00 129.00   1.00   16.00    --   92.50 -88.00  94.22   25
  5  ω     70.00  95.00   1.00   16.00    --   92.50-126.00 150.00   25
  6  ω     68.00  93.00   1.00   16.00    --   92.50-126.00  30.00   25
  7  ω     83.00 109.00   1.00   16.00    --   92.50 -92.00 -48.26   26
  8  ω     63.00  89.00   1.00   16.00    --   92.50-126.00 -60.00   26
  9  ω     95.00 124.00   1.00   16.00    --   92.50 -77.00-150.00   29
 10  ω     96.00 151.00   1.00   16.00    --   92.50  30.00-180.00   55
 11  ω    114.00 140.00   1.00   16.00    --   92.50  77.00-120.00   26
 12  ω     78.00 104.00   1.00   16.00    --   92.50  45.00-120.00   26
 13  ω     64.00 165.00   1.00   16.00    --   92.50  61.00-120.00  101
 14  ω    117.00 148.00   1.00   16.00    --   92.50 126.00  60.00   31
 15  ω     27.00  97.00   1.00   16.00    --   92.50 -45.00  30.00   70
 16  ω     32.00 124.00   1.00   16.00    --   92.50 -72.00 159.47   92
 17  ω     28.00  65.00   1.00   16.00    --   92.50 -95.00  90.00   37
 18  ω     20.00  58.00   1.00   16.00    --   92.50-130.00  75.00   38
 19  ω     19.00  63.00   1.00   16.00    --   92.50 -93.00  60.02   44
 20  ω     18.00  45.00   1.00   16.00    --   92.50 -95.00  30.00   27
 21  ω      9.00  35.00   1.00   16.00    --   92.50 -88.00  94.22   26
 22  ω     25.00  94.00   1.00    4.00    --   41.46  38.00-150.00   69
 23  ω     19.00  62.00   1.00   16.00    --   92.50-126.00-180.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1118018000
_diffrn_orient_matrix_UB_12      -0.0514519000
_diffrn_orient_matrix_UB_13      -0.0232736000
_diffrn_orient_matrix_UB_21      0.0450864000
_diffrn_orient_matrix_UB_22      0.1335176000
_diffrn_orient_matrix_UB_23      -0.0048726000
_diffrn_orient_matrix_UB_31      0.0446966000
_diffrn_orient_matrix_UB_32      -0.0065310000
_diffrn_orient_matrix_UB_33      0.0844486000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3663
_reflns_number_total             4027
_reflns_odcompleteness_completeness 99.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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         1.960
_refine_diff_density_min         -2.043
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.071
_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)+(0.0555P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0808
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C8(H8), C21(H21), C9(H9), C18(H18), C17(H17), C5(H5),
 C22(H22), C25(H25), C24(H24), C15(H15), C4(H4), C11(H11), C3(H3), C10(H10),
 C6(H6), C12(H12)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C26(H26A,H26B,H26C)
;
_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 0.71509(2) 0.09571(2) 0.21423(2) 0.01855(9) Uani 1 1 d . . . . .
P1 P 0.85533(9) -0.16310(9) 0.14982(5) 0.0183(2) Uani 1 1 d . . . . .
C2 C 0.6033(4) 0.1157(4) 0.0438(3) 0.0242(9) Uani 1 1 d . . . . .
H2 H 0.610793 0.027906 0.045184 0.029 Uiso 1 1 calc R . . . .
O3 O 0.7507(3) -0.5361(3) -0.09475(16) 0.0266(7) Uani 1 1 d . . . . .
O4 O 1.3079(3) 0.0578(3) 0.13758(18) 0.0275(7) Uani 1 1 d . . . . .
C1 C 0.6386(3) 0.1857(4) 0.1071(2) 0.0204(8) Uani 1 1 d . . . . .
C14 C 0.8775(4) -0.3925(4) 0.0806(3) 0.0206(9) Uani 1 1 d . . . . .
H14 H 0.928037 -0.411247 0.123491 0.025 Uiso 1 1 calc R . . . .
C8 C 0.9214(4) 0.2018(4) 0.1344(2) 0.0217(9) Uani 1 1 d . . . . .
H8 H 0.883106 0.163764 0.091089 0.026 Uiso 1 1 calc R . . . .
C21 C 1.0452(4) -0.0916(4) 0.0785(3) 0.0200(9) Uani 1 1 d . . . . .
H21 H 1.006451 -0.118426 0.032079 0.024 Uiso 1 1 calc R . . . .
C19 C 0.7989(4) -0.6580(4) -0.0892(3) 0.0300(10) Uani 1 1 d . . . . .
H19A H 0.880166 -0.651696 -0.089971 0.045 Uiso 1 1 calc GR . . . .
H19B H 0.768556 -0.708488 -0.132390 0.045 Uiso 1 1 calc GR . . . .
H19C H 0.780979 -0.696976 -0.041484 0.045 Uiso 1 1 calc GR . . . .
C9 C 1.0217(4) 0.2633(4) 0.1276(2) 0.0256(9) Uani 1 1 d . . . . .
H9 H 1.051997 0.267118 0.079581 0.031 Uiso 1 1 calc R . . . .
C13 C 0.8277(3) -0.2760(4) 0.0755(2) 0.0186(8) Uani 1 1 d . . . . .
C18 C 0.7510(4) -0.2510(4) 0.0128(2) 0.0211(8) Uani 1 1 d . . . . .
H18 H 0.715897 -0.171971 0.008156 0.025 Uiso 1 1 calc R . . . .
C23 C 1.2064(3) 0.0033(4) 0.1450(2) 0.0211(8) Uani 1 1 d . . . . .
C7 C 0.8773(3) 0.1963(4) 0.2045(2) 0.0184(8) Uani 1 1 d . . . . .
C17 C 0.7262(4) -0.3406(4) -0.0424(2) 0.0237(9) Uani 1 1 d . . . . .
H17 H 0.672903 -0.323723 -0.084030 0.028 Uiso 1 1 calc R . . . .
C5 C 0.5846(4) 0.3716(5) 0.0382(3) 0.0258(9) Uani 1 1 d . . . . .
H5 H 0.579346 0.459594 0.035998 0.031 Uiso 1 1 calc R . . . .
C22 C 1.1491(4) -0.0368(4) 0.0774(2) 0.0233(9) Uani 1 1 d . . . . .
H22 H 1.181388 -0.026353 0.030467 0.028 Uiso 1 1 calc R . . . .
C20 C 0.9964(4) -0.1080(4) 0.1473(3) 0.0200(9) Uani 1 1 d . . . . .
C25 C 1.0553(4) -0.0687(4) 0.2145(2) 0.0219(8) Uani 1 1 d . . . . .
H25 H 1.023769 -0.080207 0.261676 0.026 Uiso 1 1 calc R . . . .
C16 C 0.7796(4) -0.4560(4) -0.0368(2) 0.0235(9) Uani 1 1 d . . . . .
C24 C 1.1592(4) -0.0129(4) 0.2139(2) 0.0241(9) Uani 1 1 d . . . . .
H24 H 1.198028 0.014080 0.260170 0.029 Uiso 1 1 calc R . . . .
C15 C 0.8552(4) -0.4823(4) 0.0247(2) 0.0225(8) Uani 1 1 d . . . . .
H15 H 0.891514 -0.560724 0.028647 0.027 Uiso 1 1 calc R . . . .
C4 C 0.5468(4) 0.3011(5) -0.0246(2) 0.0282(10) Uani 1 1 d . . . . .
H4 H 0.514068 0.340586 -0.069262 0.034 Uiso 1 1 calc R . . . .
C11 C 1.0333(4) 0.3131(5) 0.2606(3) 0.0302(10) Uani 1 1 d . . . . .
H11 H 1.071916 0.350796 0.303961 0.036 Uiso 1 1 calc R . . . .
C3 C 0.5567(4) 0.1741(5) -0.0221(3) 0.0293(10) Uani 1 1 d . . . . .
H3 H 0.531769 0.125872 -0.065390 0.035 Uiso 1 1 calc R . . . .
C10 C 1.0775(4) 0.3185(4) 0.1903(3) 0.0273(9) Uani 1 1 d . . . . .
H10 H 1.146142 0.360329 0.185418 0.033 Uiso 1 1 calc R . . . .
C6 C 0.6300(3) 0.3144(4) 0.1043(2) 0.0224(9) Uani 1 1 d . . . . .
H6 H 0.655131 0.362868 0.147444 0.027 Uiso 1 1 calc R . . . .
O2 O 0.8479(3) -0.2230(3) 0.22659(16) 0.0247(6) Uani 1 1 d . . . . .
C12 C 0.9326(4) 0.2525(5) 0.2675(2) 0.0268(9) Uani 1 1 d . . . . .
H12 H 0.901739 0.249710 0.315409 0.032 Uiso 1 1 calc R . . . .
C26 C 1.3583(4) 0.1256(5) 0.2024(3) 0.0328(11) Uani 1 1 d . . . . .
H26A H 1.304812 0.186544 0.218959 0.049 Uiso 1 1 calc GR . . . .
H26B H 1.425175 0.168699 0.187988 0.049 Uiso 1 1 calc GR . . . .
H26C H 1.378973 0.067689 0.244091 0.049 Uiso 1 1 calc GR . . . .
O1 O 0.7760(2) -0.0555(3) 0.13146(16) 0.0233(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C1 2.248(4) . ?
Bi1 C7 2.250(4) . ?
Bi1 O2 2.368(3) 2_655 ?
Bi1 O1 2.344(3) . ?
P1 C13 1.796(4) . ?
P1 C20 1.800(5) . ?
P1 O2 1.508(3) . ?
P1 O1 1.518(3) . ?
C2 C1 1.381(6) . ?
C2 C3 1.395(7) . ?
O3 C19 1.434(6) . ?
O3 C16 1.359(5) . ?
O4 C23 1.370(5) . ?
O4 C26 1.444(6) . ?
C1 C6 1.390(6) . ?
C14 C13 1.389(6) . ?
C14 C15 1.391(6) . ?
C8 C9 1.389(6) . ?
C8 C7 1.385(6) . ?
C21 C22 1.383(6) . ?
C21 C20 1.403(6) . ?
C9 C10 1.376(7) . ?
C13 C18 1.404(6) . ?
C18 C17 1.384(6) . ?
C23 C22 1.393(6) . ?
C23 C24 1.393(6) . ?
C7 C12 1.384(6) . ?
C17 C16 1.398(7) . ?
C5 C4 1.386(7) . ?
C5 C6 1.388(6) . ?
C20 C25 1.393(7) . ?
C25 C24 1.386(7) . ?
C16 C15 1.383(6) . ?
C4 C3 1.373(7) . ?
C11 C10 1.391(7) . ?
C11 C12 1.389(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 Bi1 C7 91.37(14) . . ?
C1 Bi1 O2 83.74(13) . 2_655 ?
C1 Bi1 O1 84.49(13) . . ?
C7 Bi1 O2 87.04(13) . 2_655 ?
C7 Bi1 O1 88.18(13) . . ?
O1 Bi1 O2 167.19(10) . 2_655 ?
C13 P1 C20 108.8(2) . . ?
O2 P1 C13 110.05(18) . . ?
O2 P1 C20 106.87(19) . . ?
O2 P1 O1 115.70(17) . . ?
O1 P1 C13 106.70(18) . . ?
O1 P1 C20 108.61(18) . . ?
C1 C2 C3 120.0(4) . . ?
C16 O3 C19 117.0(3) . . ?
C23 O4 C26 117.3(4) . . ?
C2 C1 Bi1 121.2(3) . . ?
C2 C1 C6 119.9(4) . . ?
C6 C1 Bi1 118.9(3) . . ?
C13 C14 C15 121.8(4) . . ?
C7 C8 C9 119.8(4) . . ?
C22 C21 C20 120.6(4) . . ?
C10 C9 C8 120.3(4) . . ?
C14 C13 P1 120.8(3) . . ?
C14 C13 C18 118.3(4) . . ?
C18 C13 P1 120.8(3) . . ?
C17 C18 C13 120.5(4) . . ?
O4 C23 C22 115.5(4) . . ?
O4 C23 C24 124.7(4) . . ?
C22 C23 C24 119.8(4) . . ?
C8 C7 Bi1 119.2(3) . . ?
C12 C7 Bi1 120.6(3) . . ?
C12 C7 C8 120.2(4) . . ?
C18 C17 C16 120.0(4) . . ?
C4 C5 C6 120.3(5) . . ?
C21 C22 C23 120.2(4) . . ?
C21 C20 P1 121.7(3) . . ?
C25 C20 P1 119.5(3) . . ?
C25 C20 C21 118.5(4) . . ?
C24 C25 C20 121.2(4) . . ?
O3 C16 C17 115.1(4) . . ?
O3 C16 C15 124.6(4) . . ?
C15 C16 C17 120.3(4) . . ?
C25 C24 C23 119.7(4) . . ?
C16 C15 C14 119.1(4) . . ?
C3 C4 C5 119.9(4) . . ?
C12 C11 C10 120.0(4) . . ?
C4 C3 C2 120.2(4) . . ?
C9 C10 C11 120.0(4) . . ?
C5 C6 C1 119.7(4) . . ?
P1 O2 Bi1 142.47(18) . 2_645 ?
C7 C12 C11 119.8(4) . . ?
P1 O1 Bi1 128.42(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.374
_oxdiff_exptl_absorpt_empirical_full_min 0.728
####################################################################### 
# 
# 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_bp2dm
_database_code_depnum_ccdc_archive 'CCDC 1943309'
loop_
_audit_author_name
_audit_author_address
'Megan Herdman'
;Monash University
Australia
;
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;
_audit_creation_date             2019-02-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        'diphenyl bismuth mono-dimethylphosphinate'
_chemical_formula_moiety         'C14 H16 Bi O2 P'
_chemical_formula_sum            'C14 H16 Bi O2 P'
_chemical_formula_weight         456.22
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Bi1 P1 O2 C14 H16'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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                   9.0005(2)
_cell_length_b                   16.2512(3)
_cell_length_c                   10.0290(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1466.93(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7135
_cell_measurement_temperature    123.00(13)
_cell_measurement_theta_max      66.8380
_cell_measurement_theta_min      5.1710
_shelx_estimated_absorpt_T_max   0.130
_shelx_estimated_absorpt_T_min   0.089
_exptl_absorpt_coefficient_mu    24.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.066
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15386
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.836
_diffrn_reflns_theta_max         66.836
_diffrn_reflns_theta_min         5.182
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  65.00   1.00    1.00    --   41.46 -38.00 -30.00   94
  2  ω     13.00  39.00   1.00    3.00    --   92.50 -87.00 -34.66   26
  3  ω     38.00  64.00   1.00    3.00    --   92.50 -61.00 -30.00   26
  4  ω     75.00 104.00   1.00    3.00    --   92.50 -92.00  13.44   29
  5  ω     79.00 106.00   1.00    3.00    --   92.50 -92.00  45.03   27
  6  ω     80.00 107.00   1.00    3.00    --   92.50 -61.00 -30.00   27
  7  ω     73.00  99.00   1.00    3.00    --   92.50 -87.00 -34.66   26
  8  ω     70.00 115.00   1.00    3.00    --   92.50 -93.00 -92.19   45
  9  ω     96.00 130.00   1.00    3.00    --   92.50 -93.00-131.57   34
 10  ω     66.00 110.00   1.00    3.00    --   92.50 -61.00-150.00   44
 11  ω     56.00  82.00   1.00    3.00    --   92.50 -93.00-131.57   26
 12  ω     50.00  75.00   1.00    3.00    --   92.50 -77.00 -90.00   25
 13  ω     41.00  83.00   1.00    3.00    --   92.50 -95.00-150.00   42
 14  ω     40.00 117.00   1.00    3.00    --   92.50 -45.00-180.00   77
 15  ω     64.00 160.00   1.00    3.00    --   92.50  30.00-150.00   96
 16  ω    135.00 166.00   1.00    3.00    --   92.50  77.00-180.00   31
 17  ω    104.00 134.00   1.00    3.00    --   92.50  61.00 -90.00   30
 18  ω    102.00 128.00   1.00    3.00    --   92.50  77.00 -30.00   26
 19  ω     96.00 135.00   1.00    3.00    --   92.50  30.00 -90.00   39
 20  ω     65.00  91.00   1.00    3.00    --   92.50  77.00-180.00   26
 21  ω     24.00  97.00   1.00    1.00    --   41.46  38.00 -90.00   73
 22  ω     63.00  93.00   1.00    3.00    --   92.50  77.00 -30.00   30
 23  ω     83.00 161.00   1.00    3.00    --   92.50  77.00  90.00   78
 24  ω    117.00 144.00   1.00    3.00    --   92.50 126.00 150.00   27
 25  ω     94.00 138.00   1.00    3.00    --   92.50 -15.00  90.00   44
 26  ω     94.00 128.00   1.00    3.00    --   92.50 -92.00 135.19   34
 27  ω     61.00  93.00   1.00    3.00    --   92.50 -61.00  90.00   32
 28  ω     57.00  98.00   1.00    3.00    --   92.50 -45.00  60.00   41
 29  ω     19.00 111.00   1.00    1.00    --   41.46  38.00 150.00   92
 30  ω     20.00  65.00   1.00    3.00    --   92.50 -15.00  90.00   45
 31  ω     10.00 125.00   1.00    3.00    --   92.50 -89.00  90.57  115
 32  ω     20.00  84.00   1.00    3.00    --   92.50-126.00  60.00   64
 33  ω     12.00  37.00   1.00    3.00    --   92.50 -92.00  13.44   25
 34  ω     12.00  37.00   1.00    3.00    --   92.50 -95.00   0.00   25
 35  ω     16.00  41.00   1.00    3.00    --   92.50 -95.00-180.00   25
 36  ω    -98.00 -58.00   1.00    1.00    --  -41.46 126.00-120.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1554018000
_diffrn_orient_matrix_UB_12      -0.0122885000
_diffrn_orient_matrix_UB_13      -0.0391138000
_diffrn_orient_matrix_UB_21      0.0256729000
_diffrn_orient_matrix_UB_22      -0.1503666000
_diffrn_orient_matrix_UB_23      -0.0133060000
_diffrn_orient_matrix_UB_31      -0.0670385000
_diffrn_orient_matrix_UB_32      -0.0288921000
_diffrn_orient_matrix_UB_33      0.0853103000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2470
_reflns_number_total             2595
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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         0.588
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 
;
 Flack x determined using 1005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.034(8)
_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     165
_refine_ls_number_reflns         2595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0192
_refine_ls_restrained_S_all      1.044
_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)+(0.0286P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0454
_refine_ls_wR_factor_ref         0.0463
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C14(H14), C11(H11), C13(H13), C4(H4), C8(H8), C7(H7),
 C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C2'(H2'A,H2'B,H2'C)
;
_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
Bi1' Bi 0.62053(2) 0.24876(2) 0.53293(2) 0.01604(9) Uani 1 1 d . . . . .
P1' P 0.36120(15) 0.40031(8) 0.63747(13) 0.0133(3) Uani 1 1 d . . . . .
C9 C 0.4522(6) 0.1558(3) 0.6078(7) 0.0144(12) Uani 1 1 d . . . . .
C10 C 0.3771(6) 0.1711(3) 0.7258(6) 0.0185(12) Uani 1 1 d . . . . .
H10 H 0.401147 0.217144 0.776358 0.022 Uiso 1 1 calc R . . . .
O2' O 0.2480(5) 0.3691(3) 0.5402(5) 0.0276(11) Uani 1 1 d . . . . .
O1' O 0.4940(5) 0.3451(2) 0.6624(5) 0.0210(10) Uani 1 1 d . . . . .
C12 C 0.2329(7) 0.0483(4) 0.6950(8) 0.0267(15) Uani 1 1 d . . . . .
H12 H 0.158859 0.012436 0.723314 0.032 Uiso 1 1 calc R . . . .
C14 C 0.4214(7) 0.0851(4) 0.5340(7) 0.0228(13) Uani 1 1 d . . . . .
H14 H 0.474031 0.073323 0.456439 0.027 Uiso 1 1 calc R . . . .
C1' C 0.2735(8) 0.4192(4) 0.7932(8) 0.0294(16) Uani 1 1 d . . . . .
H1'A H 0.188361 0.453827 0.779879 0.044 Uiso 1 1 calc GR . . . .
H1'B H 0.342154 0.446003 0.852152 0.044 Uiso 1 1 calc GR . . . .
H1'C H 0.242464 0.367907 0.831769 0.044 Uiso 1 1 calc GR . . . .
C11 C 0.2662(6) 0.1181(4) 0.7690(7) 0.0208(14) Uani 1 1 d . . . . .
H11 H 0.214440 0.129354 0.847187 0.025 Uiso 1 1 calc R . . . .
C2' C 0.4258(7) 0.4975(4) 0.5798(7) 0.0218(14) Uani 1 1 d . . . . .
H2'A H 0.474622 0.490678 0.495357 0.033 Uiso 1 1 calc GR . . . .
H2'B H 0.494620 0.520024 0.643176 0.033 Uiso 1 1 calc GR . . . .
H2'C H 0.343116 0.534284 0.569603 0.033 Uiso 1 1 calc GR . . . .
C13 C 0.3104(7) 0.0325(4) 0.5790(8) 0.0295(16) Uani 1 1 d . . . . .
H13 H 0.287771 -0.014326 0.529806 0.035 Uiso 1 1 calc R . . . .
C3 C 0.7657(5) 0.2386(4) 0.7169(6) 0.0155(12) Uani 1 1 d . . . . .
C4 C 0.8059(7) 0.3092(4) 0.7843(8) 0.0242(16) Uani 1 1 d . . . . .
H4 H 0.772786 0.360431 0.755441 0.029 Uiso 1 1 calc R . . . .
C8 C 0.8142(7) 0.1628(4) 0.7588(7) 0.0197(15) Uani 1 1 d . . . . .
H8 H 0.787335 0.115536 0.712368 0.024 Uiso 1 1 calc R . . . .
C7 C 0.9039(7) 0.1572(4) 0.8715(7) 0.0259(14) Uani 1 1 d . . . . .
H7 H 0.935572 0.105850 0.901065 0.031 Uiso 1 1 calc R . . . .
C5 C 0.8964(8) 0.3027(4) 0.8960(8) 0.0317(16) Uani 1 1 d . . . . .
H5 H 0.923819 0.349947 0.942054 0.038 Uiso 1 1 calc R . . . .
C6 C 0.9463(7) 0.2269(5) 0.9395(8) 0.0318(19) Uani 1 1 d . . . . .
H6 H 1.007781 0.223072 1.013833 0.038 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' C9 2.267(6) . ?
Bi1' O2' 2.350(4) 4_556 ?
Bi1' O1' 2.331(4) . ?
Bi1' C3 2.267(6) . ?
P1' O2' 1.499(5) . ?
P1' O1' 1.515(4) . ?
P1' C1' 1.777(7) . ?
P1' C2' 1.780(6) . ?
C9 C10 1.385(9) . ?
C9 C14 1.396(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(9) . ?
C12 H12 0.9300 . ?
C12 C11 1.389(10) . ?
C12 C13 1.380(11) . ?
C14 H14 0.9300 . ?
C14 C13 1.390(9) . ?
C1' H1'A 0.9600 . ?
C1' H1'B 0.9600 . ?
C1' H1'C 0.9600 . ?
C11 H11 0.9300 . ?
C2' H2'A 0.9600 . ?
C2' H2'B 0.9600 . ?
C2' H2'C 0.9600 . ?
C13 H13 0.9300 . ?
C3 C4 1.381(9) . ?
C3 C8 1.373(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(11) . ?
C8 H8 0.9300 . ?
C8 C7 1.391(10) . ?
C7 H7 0.9300 . ?
C7 C6 1.377(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(11) . ?
C6 H6 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
C9 Bi1' O2' 83.51(18) . 4_556 ?
C9 Bi1' O1' 86.34(18) . . ?
O1' Bi1' O2' 163.68(18) . 4_556 ?
C3 Bi1' C9 93.8(2) . . ?
C3 Bi1' O2' 85.01(19) . 4_556 ?
C3 Bi1' O1' 82.96(19) . . ?
O2' P1' O1' 116.3(3) . . ?
O2' P1' C1' 109.2(3) . . ?
O2' P1' C2' 108.1(3) . . ?
O1' P1' C1' 107.9(3) . . ?
O1' P1' C2' 108.8(3) . . ?
C1' P1' C2' 106.1(3) . . ?
C10 C9 Bi1' 119.4(4) . . ?
C10 C9 C14 120.2(6) . . ?
C14 C9 Bi1' 120.4(5) . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.5(6) . . ?
C11 C10 H10 119.7 . . ?
P1' O2' Bi1' 144.2(3) . 4_456 ?
P1' O1' Bi1' 133.7(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C13 C12 C11 119.6(6) . . ?
C9 C14 H14 120.8 . . ?
C13 C14 C9 118.4(6) . . ?
C13 C14 H14 120.8 . . ?
P1' C1' H1'A 109.5 . . ?
P1' C1' H1'B 109.5 . . ?
P1' C1' H1'C 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
C10 C11 C12 119.7(6) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
P1' C2' H2'A 109.5 . . ?
P1' C2' H2'B 109.5 . . ?
P1' C2' H2'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
C12 C13 C14 121.5(7) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C4 C3 Bi1' 119.3(5) . . ?
C8 C3 Bi1' 119.9(5) . . ?
C8 C3 C4 120.9(6) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(6) . . ?
C5 C4 H4 120.5 . . ?
C3 C8 H8 120.3 . . ?
C3 C8 C7 119.5(6) . . ?
C7 C8 H8 120.3 . . ?
C8 C7 H7 119.7 . . ?
C6 C7 C8 120.6(6) . . ?
C6 C7 H7 119.7 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(6) . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 119.1(6) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.820
_oxdiff_exptl_absorpt_empirical_full_min 0.707
