#------------------------------------------------------------------------------
#$Date: 2020-05-05 16:18:47 +0300 (Tue, 05 May 2020) $
#$Revision: 251619 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/36/7703698.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_7703698
loop_
_publ_author_name
'Murphy, Maia C.'
'Trofimova, Alina'
'LaFortune, James H. W.'
'Vogels, Christopher M.'
'Geier, Stephen J.'
'Binder, Justin F.'
'Macdonald, Charles L. B.'
'Stephan, Douglas W.'
'Westcott, Stephen A.'
_publ_section_title
;
 The phosphinoboration of acyl chlorides.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5092
_journal_page_last               5099
_journal_paper_doi               10.1039/d0dt00579g
_journal_volume                  49
_journal_year                    2020
_chemical_formula_sum            'C25 H27 O P'
_chemical_formula_weight         374.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-02-15 deposited with the CCDC.	2020-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                99.213(7)
_cell_angle_beta                 105.491(8)
_cell_angle_gamma                107.793(7)
_cell_formula_units_Z            2
_cell_length_a                   8.317(3)
_cell_length_b                   11.854(4)
_cell_length_c                   11.878(3)
_cell_measurement_reflns_used    3740
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      2.68
_cell_volume                     1036.6(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28397
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_min         2.734
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         5148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0491
_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)+(0.0371P)²+0.3604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3407
_reflns_number_total             5148
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00579g2.cif
_cod_data_source_block           jl_a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7703695--7703698.cif.'
_cod_original_cell_volume        1036.7(5)
_cod_database_code               7703698
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.990
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.45489(6) 0.69694(5) 0.26364(4) 0.01984(13) Uani 1 1 d . . . . .
O1 O 0.71943(19) 0.91713(13) 0.35513(12) 0.0323(3) Uani 1 1 d . . . . .
C1 C 0.7094(2) 0.81000(17) 0.50688(15) 0.0209(4) Uani 1 1 d . . . . .
C2 C 0.8608(2) 0.90356(18) 0.59205(16) 0.0258(4) Uani 1 1 d . . . . .
H2A H 0.9131 0.9777 0.5723 0.031 Uiso 1 1 calc R U . . .
C3 C 0.9350(3) 0.8888(2) 0.70511(18) 0.0327(5) Uani 1 1 d . . . . .
H3A H 1.0386 0.9524 0.7628 0.039 Uiso 1 1 calc R U . . .
C4 C 0.8582(3) 0.7810(2) 0.73416(18) 0.0348(5) Uani 1 1 d . . . . .
H4A H 0.9093 0.7709 0.8118 0.042 Uiso 1 1 calc R U . . .
C5 C 0.7074(3) 0.6881(2) 0.65056(17) 0.0315(5) Uani 1 1 d . . . . .
H5A H 0.6550 0.6144 0.6709 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6327(3) 0.70239(19) 0.53755(16) 0.0253(4) Uani 1 1 d . . . . .
H6A H 0.5287 0.6386 0.4805 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6382(2) 0.82818(17) 0.38379(16) 0.0219(4) Uani 1 1 d . . . . .
C8 C 0.2431(2) 0.65057(16) 0.29425(15) 0.0187(4) Uani 1 1 d . . . . .
C9 C 0.2009(2) 0.71281(17) 0.38762(15) 0.0206(4) Uani 1 1 d . . . . .
C10 C 0.0387(3) 0.65512(19) 0.40462(17) 0.0256(4) Uani 1 1 d . . . . .
H10A H 0.0114 0.6958 0.4686 0.031 Uiso 1 1 calc R U . . .
C11 C -0.0840(3) 0.54124(18) 0.33232(18) 0.0263(4) Uani 1 1 d . . . . .
C12 C -0.0435(3) 0.48421(18) 0.23757(17) 0.0255(4) Uani 1 1 d . . . . .
H12A H -0.1283 0.4078 0.1847 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1177(2) 0.53595(17) 0.21809(15) 0.0199(4) Uani 1 1 d . . . . .
C14 C 0.3193(3) 0.83849(18) 0.47003(17) 0.0277(4) Uani 1 1 d . . . . .
H14A H 0.2455 0.8788 0.4988 0.042 Uiso 1 1 calc R U . . .
H14B H 0.3828 0.8878 0.4255 0.042 Uiso 1 1 calc R U . . .
H14C H 0.4065 0.8307 0.5394 0.042 Uiso 1 1 calc R U . . .
C15 C -0.2575(3) 0.4815(2) 0.3537(2) 0.0391(5) Uani 1 1 d . . . . .
H15A H -0.2332 0.4865 0.4402 0.059 Uiso 1 1 calc R U . . .
H15B H -0.3127 0.3952 0.3072 0.059 Uiso 1 1 calc R U . . .
H15C H -0.3393 0.5241 0.3278 0.059 Uiso 1 1 calc R U . . .
C16 C 0.1528(3) 0.46727(17) 0.11405(16) 0.0244(4) Uani 1 1 d . . . . .
H16A H 0.0513 0.3895 0.0729 0.037 Uiso 1 1 calc R U . . .
H16B H 0.2623 0.4506 0.1452 0.037 Uiso 1 1 calc R U . . .
H16C H 0.1673 0.5173 0.0566 0.037 Uiso 1 1 calc R U . . .
C17 C 0.4316(2) 0.75793(17) 0.12998(15) 0.0203(4) Uani 1 1 d . . . . .
C18 C 0.5447(3) 0.73907(19) 0.06483(16) 0.0259(4) Uani 1 1 d . . . . .
C19 C 0.5340(3) 0.77683(19) -0.04143(17) 0.0291(5) Uani 1 1 d . . . . .
H19A H 0.6109 0.7643 -0.0845 0.035 Uiso 1 1 calc R U . . .
C20 C 0.4149(3) 0.83192(18) -0.08605(16) 0.0274(5) Uani 1 1 d . . . . .
C21 C 0.3083(3) 0.85236(17) -0.01908(16) 0.0254(4) Uani 1 1 d . . . . .
H21A H 0.2281 0.8920 -0.0475 0.031 Uiso 1 1 calc R U . . .
C22 C 0.3135(2) 0.81737(17) 0.08811(16) 0.0223(4) Uani 1 1 d . . . . .
C23 C 0.6806(3) 0.6807(2) 0.10771(19) 0.0405(6) Uani 1 1 d . . . . .
H23A H 0.7471 0.6776 0.0512 0.061 Uiso 1 1 calc R U . . .
H23B H 0.6183 0.5972 0.1111 0.061 Uiso 1 1 calc R U . . .
H23C H 0.7643 0.7297 0.1885 0.061 Uiso 1 1 calc R U . . .
C24 C 0.3993(3) 0.8673(2) -0.20416(17) 0.0369(5) Uani 1 1 d . . . . .
H24A H 0.3970 0.9504 -0.1938 0.055 Uiso 1 1 calc R U . . .
H24B H 0.2885 0.8093 -0.2670 0.055 Uiso 1 1 calc R U . . .
H24C H 0.5024 0.8651 -0.2283 0.055 Uiso 1 1 calc R U . . .
C25 C 0.1969(3) 0.8498(2) 0.15532(19) 0.0327(5) Uani 1 1 d . . . . .
H25A H 0.1309 0.8944 0.1119 0.049 Uiso 1 1 calc R U . . .
H25B H 0.2721 0.9016 0.2370 0.049 Uiso 1 1 calc R U . . .
H25C H 0.1117 0.7744 0.1608 0.049 Uiso 1 1 calc R U . . .
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
C8 P1 C17 110.68(8) . . ?
C8 P1 C7 113.72(8) . . ?
C17 P1 C7 102.35(9) . . ?
C6 C1 C2 119.27(17) . . ?
C6 C1 C7 122.44(17) . . ?
C2 C1 C7 118.27(16) . . ?
C3 C2 C1 120.22(18) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 119.92(19) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 120.25(19) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C6 C5 C4 120.06(19) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 120.28(18) . . ?
C5 C6 H6A 119.9 . . ?
C1 C6 H6A 119.9 . . ?
O1 C7 C1 120.91(17) . . ?
O1 C7 P1 118.94(14) . . ?
C1 C7 P1 118.63(13) . . ?
C13 C8 C9 119.35(16) . . ?
C13 C8 P1 113.36(13) . . ?
C9 C8 P1 127.17(14) . . ?
C10 C9 C8 118.37(17) . . ?
C10 C9 C14 117.46(17) . . ?
C8 C9 C14 124.17(17) . . ?
C11 C10 C9 122.90(18) . . ?
C11 C10 H10A 118.6 . . ?
C9 C10 H10A 118.6 . . ?
C10 C11 C12 117.76(18) . . ?
C10 C11 C15 121.41(19) . . ?
C12 C11 C15 120.82(19) . . ?
C11 C12 C13 121.82(18) . . ?
C11 C12 H12A 119.1 . . ?
C13 C12 H12A 119.1 . . ?
C12 C13 C8 119.70(17) . . ?
C12 C13 C16 118.61(17) . . ?
C8 C13 C16 121.68(16) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 119.34(16) . . ?
C22 C17 P1 126.64(14) . . ?
C18 C17 P1 114.01(14) . . ?
C19 C18 C17 119.38(18) . . ?
C19 C18 C23 118.52(17) . . ?
C17 C18 C23 122.09(16) . . ?
C20 C19 C18 122.13(18) . . ?
C20 C19 H19A 118.9 . . ?
C18 C19 H19A 118.9 . . ?
C19 C20 C21 117.54(17) . . ?
C19 C20 C24 121.46(19) . . ?
C21 C20 C24 121.00(19) . . ?
C20 C21 C22 123.01(18) . . ?
C20 C21 H21A 118.5 . . ?
C22 C21 H21A 118.5 . . ?
C21 C22 C17 118.56(17) . . ?
C21 C22 C25 117.87(17) . . ?
C17 C22 C25 123.53(16) . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
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 C8 1.8306(19) . ?
P1 C17 1.8356(18) . ?
P1 C7 1.860(2) . ?
O1 C7 1.219(2) . ?
C1 C6 1.394(3) . ?
C1 C2 1.395(3) . ?
C1 C7 1.500(2) . ?
C2 C3 1.383(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C8 C13 1.410(3) . ?
C8 C9 1.415(2) . ?
C9 C10 1.398(3) . ?
C9 C14 1.506(3) . ?
C10 C11 1.386(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.391(3) . ?
C11 C15 1.509(3) . ?
C12 C13 1.391(3) . ?
C12 H12A 0.9500 . ?
C13 C16 1.513(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C22 1.408(3) . ?
C17 C18 1.413(3) . ?
C18 C19 1.395(3) . ?
C18 C23 1.516(3) . ?
C19 C20 1.384(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.387(3) . ?
C20 C24 1.512(3) . ?
C21 C22 1.395(2) . ?
C21 H21A 0.9500 . ?
C22 C25 1.506(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
