#------------------------------------------------------------------------------
#$Date: 2023-03-10 01:59:35 +0200 (Fri, 10 Mar 2023) $
#$Revision: 281790 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/25/7712582.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_7712582
loop_
_publ_author_name
'Hong, Li-Hui'
'Feng, Wei-Jung'
'Chen, Wei-Chih'
'Chang, Yu-Chang'
_publ_section_title
;
 Highly Efficient and Well-Defined Phosphinous Acid-Ligated Pd(II)
 Precatalysts for Hirao Cross-Coupling Reaction
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT00033H
_journal_year                    2023
_chemical_formula_sum            'C26 H23 O P'
_chemical_formula_weight         382.41
_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-2018/3
_audit_update_record
;
2022-12-28 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                77.950(2)
_cell_angle_beta                 88.0780(19)
_cell_angle_gamma                79.4227(18)
_cell_formula_units_Z            2
_cell_length_a                   9.3661(5)
_cell_length_b                   9.7124(5)
_cell_length_c                   11.4886(5)
_cell_measurement_reflns_used    11211
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.8855
_cell_measurement_theta_min      2.5255
_cell_volume                     1004.68(9)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_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  0.0306
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21500
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.909
_diffrn_reflns_theta_min         2.532
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.070
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0628
_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)+(0.0834P)²+1.4732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1795
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4030
_reflns_number_total             4787
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt00033h2.cif
_cod_data_source_block           lhh004
_cod_database_code               7712582
_shelx_shelxl_version_number     2018/3
_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   0.948
_shelx_estimated_absorpt_t_max   0.988
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
P P 0.04741(6) 0.81753(6) 0.25965(5) 0.01860(19) Uani 0.905(2) 1 d . . P A 1
O O 0.10120(18) 0.94565(18) 0.19173(15) 0.0233(4) Uani 0.905(2) 1 d . . P A 1
P' P 0.0042(6) 0.7338(6) 0.3384(4) 0.0163(16) Uani 0.095(2) 1 d . . P A 2
O' O -0.0774(17) 0.6777(17) 0.4430(14) 0.022(3) Uani 0.095(2) 1 d . . P A 2
C1 C 0.1978(2) 0.6719(3) 0.3130(2) 0.0262(5) Uani 1 1 d . . . . .
C2 C 0.3313(3) 0.6936(3) 0.2660(2) 0.0304(5) Uani 1 1 d . . . . .
H2A H 0.339963 0.782589 0.215575 0.036 Uiso 1 1 calc R U . . .
C3 C 0.4532(3) 0.5867(3) 0.2917(2) 0.0338(5) Uani 1 1 d . . . . .
H3A H 0.543970 0.603427 0.257750 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4450(3) 0.4565(3) 0.3657(2) 0.0314(5) Uani 1 1 d . . . . .
C5 C 0.3107(3) 0.4356(3) 0.4139(2) 0.0357(6) Uani 1 1 d . . . . .
H5A H 0.302455 0.347691 0.466120 0.043 Uiso 1 1 calc R U . . .
C6 C 0.1882(3) 0.5419(3) 0.3867(2) 0.0331(5) Uani 1 1 d . . . . .
H6A H 0.096857 0.524884 0.419137 0.040 Uiso 1 1 calc R U . A 2
C7 C 0.5766(4) 0.3396(3) 0.3915(3) 0.0513(8) Uani 1 1 d . . . . .
H7A H 0.549835 0.255887 0.445343 0.077 Uiso 1 1 calc R U . . .
H7B H 0.613668 0.312938 0.316963 0.077 Uiso 1 1 calc R U . . .
H7C H 0.651964 0.373757 0.429015 0.077 Uiso 1 1 calc R U . . .
C8 C -0.0591(2) 0.7408(2) 0.1704(2) 0.0249(5) Uani 1 1 d . . . . .
C9 C -0.0676(3) 0.8015(3) 0.0495(2) 0.0296(5) Uani 1 1 d . . . . .
H9A H -0.027273 0.884908 0.020169 0.036 Uiso 1 1 calc R U . . .
C10 C -0.1338(3) 0.7421(3) -0.0282(2) 0.0319(5) Uani 1 1 d . . . . .
H10A H -0.140310 0.786469 -0.110214 0.038 Uiso 1 1 calc R U . . .
C11 C -0.1908(3) 0.6191(3) 0.0113(2) 0.0286(5) Uani 1 1 d . . . . .
C12 C -0.1840(3) 0.5586(3) 0.1319(2) 0.0312(5) Uani 1 1 d . . . . .
H12A H -0.223519 0.474478 0.160338 0.037 Uiso 1 1 calc R U . . .
C13 C -0.1204(3) 0.6186(3) 0.2115(2) 0.0310(5) Uani 1 1 d . . . . .
H13A H -0.118487 0.576813 0.294110 0.037 Uiso 1 1 calc R U . . .
C14 C -0.2600(4) 0.5510(3) -0.0741(3) 0.0466(7) Uani 1 1 d . . . . .
H14A H -0.293836 0.465342 -0.029876 0.070 Uiso 1 1 calc R U . . .
H14B H -0.342600 0.619371 -0.114345 0.070 Uiso 1 1 calc R U . . .
H14C H -0.188371 0.524245 -0.133355 0.070 Uiso 1 1 calc R U . . .
C15 C -0.0577(2) 0.8482(2) 0.3904(2) 0.0247(5) Uani 1 1 d . . . . .
C16 C 0.0109(3) 0.8003(3) 0.5019(2) 0.0292(5) Uani 1 1 d . . . . .
H16A H 0.108334 0.750054 0.506283 0.035 Uiso 1 1 calc R U . A 2
C17 C -0.0597(3) 0.8244(3) 0.6062(2) 0.0338(5) Uani 1 1 d . . . . .
H17A H -0.011118 0.790117 0.680675 0.041 Uiso 1 1 calc R U . . .
C18 C -0.2001(3) 0.8981(3) 0.6008(2) 0.0336(5) Uani 1 1 d . . . . .
H18A H -0.248968 0.915814 0.671457 0.040 Uiso 1 1 calc R U . . .
C19 C -0.2704(3) 0.9469(3) 0.4906(2) 0.0302(5) Uani 1 1 d . . . . .
H19A H -0.368186 0.996108 0.487929 0.036 Uiso 1 1 calc R U . . .
C20 C -0.2017(2) 0.9257(2) 0.3840(2) 0.0250(5) Uani 1 1 d . . . . .
C21 C -0.2839(3) 0.9923(3) 0.2713(2) 0.0282(5) Uani 1 1 d . . . . .
C22 C -0.2288(3) 1.0867(3) 0.1809(2) 0.0317(5) Uani 1 1 d . . . . .
H22A H -0.133171 1.103848 0.187958 0.038 Uiso 1 1 calc R U . . .
C23 C -0.3104(3) 1.1560(3) 0.0812(2) 0.0366(6) Uani 1 1 d . . . . .
H23A H -0.270576 1.219172 0.019594 0.044 Uiso 1 1 calc R U . . .
C24 C -0.4502(3) 1.1332(3) 0.0712(2) 0.0351(6) Uani 1 1 d . . . . .
H24A H -0.506686 1.182123 0.002863 0.042 Uiso 1 1 calc R U . . .
C25 C -0.5091(3) 1.0400(3) 0.1596(2) 0.0325(5) Uani 1 1 d . . . . .
H25A H -0.605345 1.024922 0.151620 0.039 Uiso 1 1 calc R U . . .
C26 C -0.4275(3) 0.9687(3) 0.2596(2) 0.0304(5) Uani 1 1 d . . . . .
H26A H -0.467365 0.904308 0.320242 0.037 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
O P C8 113.32(11) . . ?
O P C15 114.10(10) . . ?
C8 P C15 108.04(10) . . ?
O P C1 111.09(11) . . ?
C8 P C1 103.58(10) . . ?
C15 P C1 105.94(11) . . ?
C15 P' O' 72.1(7) . . ?
C15 P' C1 127.5(4) . . ?
O' P' C1 125.0(7) . . ?
C15 P' C8 116.9(3) . . ?
O' P' C8 122.5(7) . . ?
C1 P' C8 95.2(2) . . ?
C15 P' C16 40.96(18) . . ?
O' P' C16 57.6(6) . . ?
C1 P' C16 101.5(3) . . ?
C8 P' C16 157.9(3) . . ?
C15 P' C6 135.5(3) . . ?
O' P' C6 90.3(7) . . ?
C1 P' C6 37.26(14) . . ?
C8 P' C6 107.1(2) . . ?
C16 P' C6 94.9(2) . . ?
P' O' C15 52.0(5) . . ?
P' O' C16 79.5(7) . . ?
C15 O' C16 47.1(4) . . ?
C2 C1 C6 118.6(2) . . ?
C2 C1 P 114.63(19) . . ?
C6 C1 P 126.60(19) . . ?
C2 C1 P' 152.1(3) . . ?
C6 C1 P' 89.2(2) . . ?
C1 C2 C3 120.7(2) . . ?
C4 C3 C2 121.2(2) . . ?
C3 C4 C5 117.9(2) . . ?
C3 C4 C7 121.2(3) . . ?
C5 C4 C7 120.9(3) . . ?
C4 C5 C6 120.8(2) . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 P' 53.59(18) . . ?
C5 C6 P' 173.7(2) . . ?
C9 C8 C13 118.5(2) . . ?
C9 C8 P 116.14(18) . . ?
C13 C8 P 125.09(18) . . ?
C9 C8 P' 151.9(2) . . ?
C13 C8 P' 89.7(2) . . ?
C10 C9 C8 120.8(2) . . ?
C9 C10 C11 121.1(2) . . ?
C10 C11 C12 118.5(2) . . ?
C10 C11 C14 121.4(2) . . ?
C12 C11 C14 120.1(2) . . ?
C13 C12 C11 121.1(2) . . ?
C12 C13 C8 120.0(2) . . ?
P' C15 C16 98.3(3) . . ?
P' C15 C20 130.0(3) . . ?
C16 C15 C20 118.9(2) . . ?
P' C15 O' 55.9(6) . . ?
C16 C15 O' 71.5(5) . . ?
C20 C15 O' 103.7(6) . . ?
C16 C15 P 118.03(18) . . ?
C20 C15 P 122.96(17) . . ?
C17 C16 C15 121.8(2) . . ?
C17 C16 O' 108.0(5) . . ?
C15 C16 O' 61.5(5) . . ?
C17 C16 P' 148.1(2) . . ?
C15 C16 P' 40.69(18) . . ?
O' C16 P' 42.9(5) . . ?
C18 C17 C16 119.6(2) . . ?
C17 C18 C19 119.5(2) . . ?
C18 C19 C20 122.2(2) . . ?
C19 C20 C15 118.0(2) . . ?
C19 C20 C21 117.3(2) . . ?
C15 C20 C21 124.7(2) . . ?
C22 C21 C26 118.6(2) . . ?
C22 C21 C20 121.8(2) . . ?
C26 C21 C20 119.4(2) . . ?
C23 C22 C21 121.2(2) . . ?
C22 C23 C24 119.7(3) . . ?
C23 C24 C25 120.8(2) . . ?
C26 C25 C24 119.9(2) . . ?
C25 C26 C21 119.7(2) . . ?
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
P O 1.4864(17) . ?
P C8 1.806(2) . ?
P C15 1.815(2) . ?
P C1 1.823(2) . ?
P' C15 1.394(6) . ?
P' O' 1.464(16) . ?
P' C1 1.837(6) . ?
P' C8 2.022(6) . ?
P' C16 2.116(6) . ?
P' C6 2.282(6) . ?
O' C15 1.683(16) . ?
O' C16 1.816(15) . ?
C1 C2 1.380(3) . ?
C1 C6 1.382(4) . ?
C2 C3 1.388(3) . ?
C3 C4 1.383(4) . ?
C4 C5 1.389(4) . ?
C4 C7 1.506(3) . ?
C5 C6 1.391(4) . ?
C8 C9 1.389(3) . ?
C8 C13 1.400(3) . ?
C9 C10 1.377(4) . ?
C10 C11 1.382(4) . ?
C11 C12 1.386(3) . ?
C11 C14 1.513(3) . ?
C12 C13 1.385(3) . ?
C15 C16 1.402(3) . ?
C15 C20 1.415(3) . ?
C16 C17 1.391(4) . ?
C17 C18 1.373(4) . ?
C18 C19 1.397(4) . ?
C19 C20 1.400(3) . ?
C20 C21 1.491(3) . ?
C21 C22 1.387(4) . ?
C21 C26 1.420(3) . ?
C22 C23 1.377(4) . ?
C23 C24 1.379(4) . ?
C24 C25 1.385(4) . ?
C25 C26 1.384(3) . ?
