# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_solve1_a
_database_code_depnum_ccdc_archive 'CCDC 2219200'
loop_
_audit_author_name
_audit_author_address
'Connor A. Koellner'
;University of Virginia
United States of America
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;
_audit_creation_date             2022-11-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
?
?
?
_chemical_name_common            ?
_chemical_name_systematic        'phenyldiphenylphosphine oxide'
_chemical_formula_moiety         'C18 H13 O P'
_chemical_formula_sum            'C18 H13 O P'
_chemical_formula_weight         276.25
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0250(12)
_cell_length_b                   9.5951(11)
_cell_length_c                   14.1127(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.226(4)
_cell_angle_gamma                90
_cell_volume                     1355.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5316
_cell_measurement_temperature    100.03
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.7040
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0604 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.9429.
The λ/2 correction factor is Not present.
;
_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    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'crystalized from ethyl acetate at 0 degrees C'
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.075
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns.reduction_process narrow-frame
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            48219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.367
_diffrn_reflns_theta_min         2.035
_diffrn_ambient_temperature      100.03
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Photon III'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       'Kappa four--circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'one pinhole collimator 0.8 mm'
_diffrn_radiation_monochromator  'HELIOS double bounce multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3563
_reflns_number_total             5048
_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.bruker_data_scaling   
'SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction'
_computing.cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing.data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing.structure_refinement  'SHELXL--2018/3 (Sheldrick, 2018)'
_computing.structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker Instrument Service V6.2.15'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         5048
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.026
_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)+(0.0406P)²+0.7718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1096
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_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
P1 P 0.30492(4) 0.76172(4) 0.54786(3) 0.01275(9) Uani 1 1 d . . . . .
O1 O 0.27588(11) 0.81338(11) 0.44934(7) 0.0180(2) Uani 1 1 d . . . . .
C1 C 0.47356(14) 0.77607(14) 0.59854(10) 0.0131(2) Uani 1 1 d . . . . .
C2 C 0.55322(14) 0.89450(15) 0.60885(10) 0.0156(3) Uani 1 1 d . . . . .
H2 H 0.5174(18) 0.9865(19) 0.5901(13) 0.020(5) Uiso 1 1 d . . . . .
C3 C 0.68398(15) 0.88079(16) 0.64712(11) 0.0183(3) Uani 1 1 d . . . . .
H3 H 0.7383(18) 0.9604(18) 0.6534(12) 0.017(4) Uiso 1 1 d . . . . .
C4 C 0.73189(15) 0.75057(17) 0.67605(11) 0.0204(3) Uani 1 1 d . . . . .
H4 H 0.821(2) 0.741(2) 0.7029(15) 0.030(5) Uiso 1 1 d . . . . .
C5 C 0.65217(15) 0.63201(16) 0.66701(11) 0.0190(3) Uani 1 1 d . . . . .
H5 H 0.6875(18) 0.5430(19) 0.6883(13) 0.020(5) Uiso 1 1 d . . . . .
C6 C 0.52226(14) 0.64386(14) 0.62711(10) 0.0149(3) Uani 1 1 d . . . . .
C7 C 0.42467(14) 0.52937(14) 0.60781(10) 0.0154(3) Uani 1 1 d . . . . .
C8 C 0.44474(17) 0.38710(16) 0.62392(11) 0.0209(3) Uani 1 1 d . . . . .
H8 H 0.528(2) 0.351(2) 0.6503(14) 0.026(5) Uiso 1 1 d . . . . .
C9 C 0.34179(19) 0.29420(16) 0.59883(12) 0.0244(3) Uani 1 1 d . . . . .
H9 H 0.3569(19) 0.196(2) 0.6094(13) 0.023(5) Uiso 1 1 d . . . . .
C10 C 0.22042(18) 0.34069(16) 0.55820(12) 0.0241(3) Uani 1 1 d . . . . .
H10 H 0.147(2) 0.274(2) 0.5394(16) 0.038(6) Uiso 1 1 d . . . . .
C11 C 0.19962(16) 0.48237(16) 0.54144(11) 0.0204(3) Uani 1 1 d . . . . .
H11 H 0.1148(19) 0.5187(19) 0.5083(13) 0.021(5) Uiso 1 1 d . . . . .
C12 C 0.30201(15) 0.57592(14) 0.56628(10) 0.0156(3) Uani 1 1 d . . . . .
C13 C 0.19525(14) 0.84109(14) 0.62987(10) 0.0130(2) Uani 1 1 d . . . . .
C14 C 0.11495(15) 0.95189(15) 0.59695(11) 0.0167(3) Uani 1 1 d . . . . .
H14 H 0.1199(17) 0.9795(19) 0.5315(13) 0.017(4) Uiso 1 1 d . . . . .
C15 C 0.02855(15) 1.01639(15) 0.65728(11) 0.0181(3) Uani 1 1 d . . . . .
H15 H -0.0272(17) 1.0905(19) 0.6355(12) 0.016(4) Uiso 1 1 d . . . . .
C16 C 0.02307(14) 0.97141(16) 0.75063(11) 0.0177(3) Uani 1 1 d . . . . .
H16 H -0.0381(18) 1.0154(19) 0.7916(13) 0.020(5) Uiso 1 1 d . . . . .
C17 C 0.10417(15) 0.86197(15) 0.78402(11) 0.0162(3) Uani 1 1 d . . . . .
H17 H 0.1025(18) 0.8311(19) 0.8496(14) 0.021(5) Uiso 1 1 d . . . . .
C18 C 0.19018(14) 0.79622(14) 0.72408(10) 0.0146(3) Uani 1 1 d . . . . .
H18 H 0.2451(19) 0.7172(19) 0.7480(13) 0.020(5) 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
P1 O1 1.4893(11) . ?
P1 C1 1.8035(14) . ?
P1 C12 1.8021(15) . ?
P1 C13 1.8087(14) . ?
C1 C2 1.392(2) . ?
C1 C6 1.4100(19) . ?
C2 H2 0.984(18) . ?
C2 C3 1.396(2) . ?
C3 H3 0.939(18) . ?
C3 C4 1.392(2) . ?
C4 H4 0.96(2) . ?
C4 C5 1.392(2) . ?
C5 H5 0.966(18) . ?
C5 C6 1.394(2) . ?
C6 C7 1.486(2) . ?
C7 C8 1.397(2) . ?
C7 C12 1.405(2) . ?
C8 H8 0.95(2) . ?
C8 C9 1.394(2) . ?
C9 H9 0.968(19) . ?
C9 C10 1.389(3) . ?
C10 H10 1.00(2) . ?
C10 C11 1.394(2) . ?
C11 H11 1.009(18) . ?
C11 C12 1.393(2) . ?
C13 C14 1.3972(19) . ?
C13 C18 1.401(2) . ?
C14 H14 0.965(18) . ?
C14 C15 1.393(2) . ?
C15 H15 0.945(18) . ?
C15 C16 1.390(2) . ?
C16 H16 0.964(19) . ?
C16 C17 1.394(2) . ?
C17 H17 0.973(19) . ?
C17 C18 1.393(2) . ?
C18 H18 0.986(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C1 118.32(7) . . ?
O1 P1 C12 117.39(7) . . ?
O1 P1 C13 111.30(6) . . ?
C1 P1 C13 107.70(6) . . ?
C12 P1 C1 92.34(7) . . ?
C12 P1 C13 107.99(7) . . ?
C2 C1 P1 128.56(11) . . ?
C2 C1 C6 121.15(13) . . ?
C6 C1 P1 110.27(10) . . ?
C1 C2 H2 120.4(11) . . ?
C1 C2 C3 118.98(13) . . ?
C3 C2 H2 120.6(11) . . ?
C2 C3 H3 119.1(11) . . ?
C4 C3 C2 119.95(14) . . ?
C4 C3 H3 120.9(11) . . ?
C3 C4 H4 120.0(12) . . ?
C3 C4 C5 121.33(14) . . ?
C5 C4 H4 118.6(12) . . ?
C4 C5 H5 119.7(11) . . ?
C4 C5 C6 119.26(14) . . ?
C6 C5 H5 121.0(11) . . ?
C1 C6 C7 113.51(12) . . ?
C5 C6 C1 119.30(13) . . ?
C5 C6 C7 127.17(13) . . ?
C8 C7 C6 127.26(14) . . ?
C8 C7 C12 119.56(14) . . ?
C12 C7 C6 113.16(12) . . ?
C7 C8 H8 122.0(12) . . ?
C9 C8 C7 119.06(15) . . ?
C9 C8 H8 119.0(12) . . ?
C8 C9 H9 118.6(11) . . ?
C10 C9 C8 121.22(15) . . ?
C10 C9 H9 120.2(11) . . ?
C9 C10 H10 121.0(13) . . ?
C9 C10 C11 120.17(15) . . ?
C11 C10 H10 118.8(13) . . ?
C10 C11 H11 122.0(11) . . ?
C12 C11 C10 118.99(15) . . ?
C12 C11 H11 119.0(11) . . ?
C7 C12 P1 110.72(10) . . ?
C11 C12 P1 128.22(12) . . ?
C11 C12 C7 121.01(13) . . ?
C14 C13 P1 117.85(11) . . ?
C14 C13 C18 119.90(13) . . ?
C18 C13 P1 122.25(11) . . ?
C13 C14 H14 117.9(11) . . ?
C15 C14 C13 120.07(14) . . ?
C15 C14 H14 122.0(11) . . ?
C14 C15 H15 120.8(11) . . ?
C16 C15 C14 120.02(14) . . ?
C16 C15 H15 119.2(11) . . ?
C15 C16 H16 119.5(11) . . ?
C15 C16 C17 120.05(14) . . ?
C17 C16 H16 120.4(11) . . ?
C16 C17 H17 120.7(11) . . ?
C18 C17 C16 120.35(14) . . ?
C18 C17 H17 119.0(11) . . ?
C13 C18 H18 120.8(11) . . ?
C17 C18 C13 119.60(13) . . ?
C17 C18 H18 119.6(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 -177.52(11) . . . . ?
P1 C1 C6 C5 179.09(11) . . . . ?
P1 C1 C6 C7 0.45(15) . . . . ?
P1 C13 C14 C15 179.87(11) . . . . ?
P1 C13 C18 C17 179.66(11) . . . . ?
O1 P1 C1 C2 55.58(15) . . . . ?
O1 P1 C1 C6 -122.89(10) . . . . ?
O1 P1 C12 C7 123.06(10) . . . . ?
O1 P1 C12 C11 -54.26(16) . . . . ?
O1 P1 C13 C14 -9.62(13) . . . . ?
O1 P1 C13 C18 171.19(11) . . . . ?
C1 P1 C12 C7 -0.72(11) . . . . ?
C1 P1 C12 C11 -178.03(14) . . . . ?
C1 P1 C13 C14 121.60(11) . . . . ?
C1 P1 C13 C18 -57.58(13) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C1 C6 C7 C8 177.02(14) . . . . ?
C1 C6 C7 C12 -1.02(18) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C2 C1 C6 C7 -178.15(13) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 C1 -1.3(2) . . . . ?
C4 C5 C6 C7 177.17(14) . . . . ?
C5 C6 C7 C8 -1.5(2) . . . . ?
C5 C6 C7 C12 -179.53(14) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 C7 C8 C9 -178.32(14) . . . . ?
C6 C7 C12 P1 1.09(15) . . . . ?
C6 C7 C12 C11 178.63(13) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C7 C12 P1 -177.12(11) . . . . ?
C8 C7 C12 C11 0.4(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 P1 176.93(12) . . . . ?
C10 C11 C12 C7 -0.1(2) . . . . ?
C12 P1 C1 C2 178.61(14) . . . . ?
C12 P1 C1 C6 0.14(11) . . . . ?
C12 P1 C13 C14 -139.85(11) . . . . ?
C12 P1 C13 C18 40.97(14) . . . . ?
C12 C7 C8 C9 -0.4(2) . . . . ?
C13 P1 C1 C2 -71.66(14) . . . . ?
C13 P1 C1 C6 109.87(11) . . . . ?
C13 P1 C12 C7 -110.18(11) . . . . ?
C13 P1 C12 C11 72.51(15) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C14 C13 C18 C17 0.5(2) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C16 C17 C18 C13 0.3(2) . . . . ?
C18 C13 C14 C15 -0.9(2) . . . . ?

_olex2_submission_original_sample_id machan_CK_PhBPO1
_olex2_submission_special_instructions 'No special instructions were received'
