#------------------------------------------------------------------------------
#$Date: 2019-11-04 12:05:32 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222685 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/41/4034127.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_4034127
loop_
_publ_author_name
'Zhang, Yu'
'Nie, Shao-Zhen'
'Ye, Jing-Jing'
'Wang, Ji-Ping'
'Zhou, Meng-Meng'
'Zhao, Chang-Qiu'
'Li, Qiang'
_publ_section_title
;
 Functional Phosphine Derivatives Having Stationary and Flexible
 Chiralities: Their Preparation and Chirality Controlling.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8423
_journal_page_last               8439
_journal_paper_doi               10.1021/acs.joc.9b00346
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration S
_chemical_formula_sum            'C24 H33 Cl2 O P Pd'
_chemical_formula_weight         545.77
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   15.7436(13)
_cell_length_b                   15.7436(13)
_cell_length_c                   19.151(3)
_cell_measurement_reflns_used    7000
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.389
_cell_measurement_theta_min      2.588
_cell_volume                     4110.8(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17219
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.089
_diffrn_reflns_theta_min         2.587
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.230
_exptl_transmission_factor_max   0.805
_exptl_transmission_factor_min   0.693
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1684 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.025(14)
_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     267
_refine_ls_number_reflns         4882
_refine_ls_number_restraints     756
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0310P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0654
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4142
_reflns_number_total             4882
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b00346_si_001.cif
_cod_data_source_block           180703b_sq
_cod_original_cell_volume        4110.9(10)
_cod_database_code               4034127
_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   0.704
_shelx_estimated_absorpt_t_max   0.812
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
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
Pd1 Pd 0.59048(3) 0.08478(3) 0.10026(2) 0.03409(12) Uani 1 1 d . U
P1 P 0.69698(10) 0.24531(10) 0.09778(6) 0.0331(3) Uani 1 1 d . U
Cl1 Cl 0.58842(11) 0.07283(11) -0.01830(6) 0.0550(4) Uani 1 1 d . U
Cl2 Cl 0.57320(11) 0.09103(9) 0.22090(6) 0.0493(4) Uani 1 1 d . U
O1 O 0.7875(3) 0.0686(3) 0.08165(18) 0.0511(10) Uani 1 1 d . U
C1 C 0.8018(4) 0.2663(3) 0.1515(2) 0.0364(11) Uani 1 1 d . U
C2 C 0.8814(4) 0.2587(4) 0.1254(3) 0.0389(13) Uani 1 1 d . U
C3 C 0.9558(4) 0.2723(4) 0.1711(3) 0.0493(13) Uani 1 1 d . U
H3 H 1.0086 0.2675 0.1542 0.059 Uiso 1 1 calc R U
C4 C 0.9533(4) 0.2927(4) 0.2406(3) 0.0537(16) Uani 1 1 d . U
H4 H 1.0045 0.3023 0.2699 0.064 Uiso 1 1 calc R U
C5 C 0.8756(4) 0.2989(4) 0.2668(3) 0.0510(15) Uani 1 1 d . U
H5 H 0.8733 0.3119 0.3140 0.061 Uiso 1 1 calc R U
C6 C 0.8005(4) 0.2857(3) 0.2222(3) 0.0436(12) Uani 1 1 d . U
H6 H 0.7478 0.2900 0.2401 0.052 Uiso 1 1 calc R U
C7 C 0.8903(4) 0.2337(4) 0.0520(3) 0.0397(12) Uani 1 1 d . U
C8 C 0.8414(4) 0.1351(4) 0.0308(3) 0.0442(13) Uani 1 1 d . U
C9 C 0.8488(5) 0.1102(5) -0.0377(3) 0.0606(16) Uani 1 1 d . U
H9 H 0.8143 0.0452 -0.0524 0.073 Uiso 1 1 calc R U
C10 C 0.9086(5) 0.1839(6) -0.0836(3) 0.0674(19) Uani 1 1 d . U
H10 H 0.9136 0.1677 -0.1295 0.081 Uiso 1 1 calc R U
C11 C 0.9596(5) 0.2780(6) -0.0635(3) 0.0652(17) Uani 1 1 d . U
H11 H 1.0004 0.3256 -0.0953 0.078 Uiso 1 1 calc R U
C12 C 0.9520(4) 0.3055(4) 0.0045(3) 0.0534(15) Uani 1 1 d . U
H12 H 0.9878 0.3709 0.0181 0.064 Uiso 1 1 calc R U
C13 C 0.7394(5) -0.0319(4) 0.0656(3) 0.0670(18) Uani 1 1 d . U
H13A H 0.6917 -0.0458 0.0296 0.100 Uiso 1 1 calc R U
H13B H 0.7072 -0.0693 0.1066 0.100 Uiso 1 1 calc R U
H13C H 0.7865 -0.0492 0.0495 0.100 Uiso 1 1 calc R U
C14 C 0.6367(4) 0.3117(3) 0.1332(3) 0.0367(12) Uani 1 1 d . U
H14 H 0.6303 0.3015 0.1838 0.044 Uiso 1 1 calc R U
C15 C 0.6898(4) 0.4237(4) 0.1192(3) 0.0404(13) Uani 1 1 d . U
H15 H 0.6930 0.4320 0.0684 0.048 Uiso 1 1 calc R U
C16 C 0.6267(4) 0.4643(4) 0.1463(3) 0.0566(15) Uani 1 1 d . U
H16A H 0.6193 0.4547 0.1964 0.068 Uiso 1 1 calc R U
H16B H 0.6598 0.5344 0.1374 0.068 Uiso 1 1 calc R U
C17 C 0.5260(4) 0.4166(4) 0.1130(3) 0.0613(16) Uani 1 1 d . U
H17A H 0.4888 0.4449 0.1325 0.074 Uiso 1 1 calc R U
H17B H 0.5327 0.4294 0.0632 0.074 Uiso 1 1 calc R U
C18 C 0.4715(4) 0.3075(4) 0.1253(3) 0.0504(15) Uani 1 1 d . U
H18 H 0.4597 0.2961 0.1756 0.060 Uiso 1 1 calc R U
C19 C 0.5334(4) 0.2630(4) 0.1019(3) 0.0441(13) Uani 1 1 d . U
H19A H 0.5389 0.2672 0.0514 0.053 Uiso 1 1 calc R U
H19B H 0.4993 0.1940 0.1143 0.053 Uiso 1 1 calc R U
C20 C 0.7975(4) 0.4840(4) 0.1465(3) 0.0479(14) Uani 1 1 d . U
H20 H 0.8293 0.4452 0.1373 0.057 Uiso 1 1 calc R U
C21 C 0.8539(4) 0.5802(4) 0.1050(3) 0.0647(17) Uani 1 1 d . U
H21A H 0.8262 0.6212 0.1144 0.097 Uiso 1 1 calc R U
H21B H 0.8491 0.5657 0.0560 0.097 Uiso 1 1 calc R U
H21C H 0.9216 0.6136 0.1188 0.097 Uiso 1 1 calc R U
C22 C 0.8058(5) 0.5052(4) 0.2248(3) 0.0645(17) Uani 1 1 d . U
H22A H 0.8729 0.5329 0.2391 0.097 Uiso 1 1 calc R U
H22B H 0.7660 0.4452 0.2498 0.097 Uiso 1 1 calc R U
H22C H 0.7836 0.5507 0.2347 0.097 Uiso 1 1 calc R U
C23 C 0.3729(4) 0.2573(5) 0.0885(3) 0.0698(19) Uani 1 1 d . U
H23A H 0.3303 0.2772 0.1096 0.105 Uiso 1 1 calc R U
H23B H 0.3442 0.1875 0.0925 0.105 Uiso 1 1 calc R U
H23C H 0.3820 0.2756 0.0401 0.105 Uiso 1 1 calc R U
C24 C 0.7396(4) 0.2993(4) 0.0123(3) 0.0441(14) Uani 1 1 d . U
H24A H 0.7921 0.3656 0.0174 0.066 Uiso 1 1 calc R U
H24B H 0.6866 0.2988 -0.0129 0.066 Uiso 1 1 calc R U
H24C H 0.7625 0.2620 -0.0130 0.066 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 '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_3
P1 Pd1 Cl1 92.53(5) .
P1 Pd1 Cl2 90.61(5) .
Cl1 Pd1 Cl2 173.34(6) .
P1 Pd1 Cl2 174.74(5) 5
Cl1 Pd1 Cl2 91.65(5) 5
Cl2 Pd1 Cl2 85.57(5) 5
C24 P1 C1 109.6(2) .
C24 P1 C14 103.9(2) .
C1 P1 C14 111.2(2) .
C24 P1 Pd1 116.31(19) .
C1 P1 Pd1 106.99(15) .
C14 P1 Pd1 108.92(16) .
Pd1 Cl2 Pd1 92.34(4) 5
C8 O1 C13 118.9(4) .
C6 C1 C2 118.4(5) .
C6 C1 P1 118.4(4) .
C2 C1 P1 123.0(4) .
C3 C2 C1 118.7(5) .
C3 C2 C7 117.0(5) .
C1 C2 C7 124.3(5) .
C4 C3 C2 121.7(5) .
C3 C4 C5 120.2(5) .
C4 C5 C6 119.2(5) .
C5 C6 C1 121.8(6) .
C12 C7 C8 118.7(5) .
C12 C7 C2 121.5(5) .
C8 C7 C2 119.6(5) .
O1 C8 C9 124.3(5) .
O1 C8 C7 115.2(5) .
C9 C8 C7 120.5(5) .
C10 C9 C8 118.7(6) .
C11 C10 C9 121.7(6) .
C10 C11 C12 120.9(6) .
C11 C12 C7 119.3(6) .
C19 C14 C15 109.6(4) .
C19 C14 P1 106.8(3) .
C15 C14 P1 116.1(3) .
C16 C15 C14 109.0(4) .
C16 C15 C20 111.7(4) .
C14 C15 C20 115.9(4) .
C17 C16 C15 113.0(5) .
C18 C17 C16 111.0(5) .
C17 C18 C23 111.8(5) .
C17 C18 C19 110.3(5) .
C23 C18 C19 110.2(5) .
C18 C19 C14 114.6(4) .
C22 C20 C21 110.4(4) .
C22 C20 C15 114.2(5) .
C21 C20 C15 110.0(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 P1 2.2278(14) .
Pd1 Cl1 2.2771(13) .
Pd1 Cl2 2.3342(13) .
Pd1 Cl2 2.4297(13) 5
P1 C24 1.812(5) .
P1 C1 1.829(5) .
P1 C14 1.856(5) .
Cl2 Pd1 2.4297(13) 5
O1 C8 1.370(6) .
O1 C13 1.405(7) .
C1 C6 1.390(7) .
C1 C2 1.410(7) .
C2 C3 1.390(7) .
C2 C7 1.485(7) .
C3 C4 1.374(7) .
C4 C5 1.370(8) .
C5 C6 1.388(8) .
C7 C12 1.396(7) .
C7 C8 1.405(7) .
C8 C9 1.390(7) .
C9 C10 1.383(8) .
C10 C11 1.342(9) .
C11 C12 1.396(8) .
C14 C19 1.532(7) .
C14 C15 1.552(7) .
C15 C16 1.517(7) .
C15 C20 1.562(7) .
C16 C17 1.514(7) .
C17 C18 1.506(8) .
C18 C23 1.518(7) .
C18 C19 1.526(7) .
C20 C22 1.527(7) .
C20 C21 1.538(7) .
