#------------------------------------------------------------------------------
#$Date: 2023-06-05 06:41:44 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284188 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/15/7131594.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131594
loop_
_publ_author_name
'Koellner, Connor A.'
'Reid, Amelia G.'
'Machan, Charles W.'
_publ_section_title
;
 Co-electrocatalytic CO₂ reduction mediated by a
 dibenzophosphole oxide and a chromium complex.
;
_journal_issue                   42
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6359
_journal_page_last               6362
_journal_paper_doi               10.1039/d3cc00166k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C18 H13 O P'
_chemical_formula_sum            'C18 H13 O P'
_chemical_formula_weight         276.25
_chemical_name_systematic        'phenyldiphenylphosphine oxide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-11-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-11 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.226(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0250(12)
_cell_length_b                   9.5951(11)
_cell_length_c                   14.1127(17)
_cell_measurement_reflns_used    5316
_cell_measurement_temperature    100.03
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.57
_cell_volume                     1355.4(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing.cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service V6.2.15'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing.data_reduction        'SAINT V8.40B (Bruker AXS LLC, 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_refinement  'SHELXL--2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_computing.structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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_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.reduction_process narrow-frame
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.367
_diffrn_reflns_theta_min         2.035
_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
_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_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_description       block
_exptl_crystal_F_000             576
_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
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.072
_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_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0461
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3563
_reflns_number_total             5048
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc00166k3.cif
_cod_data_source_block           solve1_a
_cod_depositor_comments          'Adding full bibliography for 7131594.cif.'
_cod_database_code               7131594
_shelx_shelxl_version_number     2019/1
_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.
;
_computing.bruker_data_scaling
'SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction'
_olex2_refinement_description
;
;
_olex2_submission_original_sample_id machan_CK_PhBPO1
_olex2_submission_special_instructions 'No special instructions were received'
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'
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 . . . . .
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'
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_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_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) . . . . ?
