#------------------------------------------------------------------------------
#$Date: 2025-08-20 15:05:43 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/34/4063439.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_4063439
loop_
_publ_author_name
'Chapp, Timothy W.'
'Glueck, David S.'
'Golen, James A.'
'Moore, Curtis E.'
'Rheingold, Arnold L.'
_publ_section_title
;
 Platinum-Catalyzed Asymmetric Alkylation of Bis(isitylphosphino)ethane:
 Stereoselectivity Reversal in Successive Formation of Two P−C
 Bonds
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              378
_journal_paper_doi               10.1021/om900800z
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C54 H68 P2'
_chemical_formula_weight         779.02
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                64.4770(10)
_cell_angle_beta                 80.3910(10)
_cell_angle_gamma                73.5900(10)
_cell_formula_units_Z            1
_cell_length_a                   9.5176(8)
_cell_length_b                   10.9546(9)
_cell_length_c                   12.5468(11)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.48
_cell_measurement_theta_min      2.69
_cell_volume                     1130.86(17)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13914
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9531
_exptl_absorpt_correction_T_min  0.9470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.5800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                3846
_reflns_number_total             4175
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900800z_si_002.cif
_cod_data_source_block           glu284
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4063439
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.62778(4) 0.04289(3) 0.10697(3) 0.01482(10) Uani 1 1 d . . .
C1 C 0.50263(15) 0.20334(13) 0.11591(12) 0.0203(3) Uani 1 1 d . . .
H1A H 0.4329 0.2474 0.0520 0.024 Uiso 1 1 calc R . .
H1B H 0.4454 0.1789 0.1926 0.024 Uiso 1 1 calc R . .
C2 C 0.59024(15) 0.30402(13) 0.10412(12) 0.0186(3) Uani 1 1 d . . .
C3 C 0.59295(15) 0.34403(14) 0.19292(12) 0.0214(3) Uani 1 1 d . . .
H3A H 0.5388 0.3062 0.2653 0.026 Uiso 1 1 calc R . .
C4 C 0.67463(15) 0.44083(14) 0.17990(12) 0.0213(3) Uani 1 1 d . . .
C5 C 0.67491(17) 0.48694(16) 0.26938(14) 0.0293(3) Uani 1 1 d . . .
H5A H 0.6211 0.4507 0.3423 0.035 Uiso 1 1 calc R . .
C6 C 0.75173(18) 0.58298(16) 0.25223(15) 0.0335(4) Uani 1 1 d . . .
H6A H 0.7504 0.6131 0.3131 0.040 Uiso 1 1 calc R . .
C7 C 0.83258(17) 0.63735(15) 0.14512(15) 0.0315(4) Uani 1 1 d . . .
H7A H 0.8849 0.7045 0.1338 0.038 Uiso 1 1 calc R . .
C8 C 0.83638(16) 0.59407(15) 0.05701(14) 0.0274(3) Uani 1 1 d . . .
H8A H 0.8922 0.6306 -0.0147 0.033 Uiso 1 1 calc R . .
C9 C 0.75727(15) 0.49473(14) 0.07239(12) 0.0216(3) Uani 1 1 d . . .
C10 C 0.75518(16) 0.45038(14) -0.01807(12) 0.0237(3) Uani 1 1 d . . .
H10A H 0.8110 0.4850 -0.0902 0.028 Uiso 1 1 calc R . .
C11 C 0.67432(16) 0.35885(14) -0.00298(12) 0.0224(3) Uani 1 1 d . . .
H11A H 0.6741 0.3312 -0.0650 0.027 Uiso 1 1 calc R . .
C12 C 0.68246(14) -0.06827(13) 0.26082(11) 0.0147(3) Uani 1 1 d . . .
C13 C 0.83233(14) -0.08802(13) 0.27801(11) 0.0163(3) Uani 1 1 d . . .
C14 C 0.89192(14) -0.18855(13) 0.38426(11) 0.0174(3) Uani 1 1 d . . .
H14A H 0.9929 -0.2026 0.3941 0.021 Uiso 1 1 calc R . .
C15 C 0.80997(14) -0.26872(13) 0.47603(11) 0.0163(3) Uani 1 1 d . . .
C16 C 0.66090(14) -0.24082(13) 0.46158(11) 0.0165(3) Uani 1 1 d . . .
H16A H 0.6016 -0.2911 0.5250 0.020 Uiso 1 1 calc R . .
C17 C 0.59499(14) -0.14131(13) 0.35701(11) 0.0156(3) Uani 1 1 d . . .
C18 C 0.93273(15) -0.00098(14) 0.18770(12) 0.0201(3) Uani 1 1 d . . .
H18A H 0.8741 0.0668 0.1178 0.024 Uiso 1 1 calc R . .
C19 C 1.06280(16) -0.09018(16) 0.14449(13) 0.0266(3) Uani 1 1 d . . .
H19A H 1.0269 -0.1419 0.1119 0.040 Uiso 1 1 calc R . .
H19B H 1.1242 -0.1558 0.2108 0.040 Uiso 1 1 calc R . .
H19C H 1.1209 -0.0301 0.0829 0.040 Uiso 1 1 calc R . .
C20 C 0.98416(17) 0.08301(16) 0.23830(14) 0.0287(3) Uani 1 1 d . . .
H20A H 0.8988 0.1363 0.2683 0.043 Uiso 1 1 calc R . .
H20B H 1.0377 0.1471 0.1760 0.043 Uiso 1 1 calc R . .
H20C H 1.0488 0.0193 0.3030 0.043 Uiso 1 1 calc R . .
C21 C 0.88457(15) -0.37658(13) 0.58870(11) 0.0183(3) Uani 1 1 d . . .
H21A H 0.9865 -0.4166 0.5647 0.022 Uiso 1 1 calc R . .
C22 C 0.81110(17) -0.49766(14) 0.65717(12) 0.0247(3) Uani 1 1 d . . .
H22A H 0.8637 -0.5618 0.7289 0.037 Uiso 1 1 calc R . .
H22B H 0.8134 -0.5471 0.6076 0.037 Uiso 1 1 calc R . .
H22C H 0.7091 -0.4619 0.6790 0.037 Uiso 1 1 calc R . .
C23 C 0.89784(17) -0.30568(15) 0.66724(12) 0.0248(3) Uani 1 1 d . . .
H23A H 0.9449 -0.3758 0.7399 0.037 Uiso 1 1 calc R . .
H23B H 0.7999 -0.2586 0.6873 0.037 Uiso 1 1 calc R . .
H23C H 0.9572 -0.2372 0.6247 0.037 Uiso 1 1 calc R . .
C24 C 0.42896(14) -0.11647(14) 0.35506(11) 0.0177(3) Uani 1 1 d . . .
H24A H 0.3972 -0.0396 0.2773 0.021 Uiso 1 1 calc R . .
C25 C 0.38476(16) -0.24555(15) 0.36581(13) 0.0236(3) Uani 1 1 d . . .
H25A H 0.2777 -0.2264 0.3661 0.035 Uiso 1 1 calc R . .
H25B H 0.4194 -0.3240 0.4396 0.035 Uiso 1 1 calc R . .
H25C H 0.4289 -0.2688 0.2986 0.035 Uiso 1 1 calc R . .
C26 C 0.34987(15) -0.06924(16) 0.45291(12) 0.0247(3) Uani 1 1 d . . .
H26A H 0.2437 -0.0541 0.4504 0.037 Uiso 1 1 calc R . .
H26B H 0.3730 0.0177 0.4407 0.037 Uiso 1 1 calc R . .
H26C H 0.3824 -0.1412 0.5301 0.037 Uiso 1 1 calc R . .
C27 C 0.50169(15) -0.03179(14) 0.06823(11) 0.0175(3) Uani 1 1 d . . .
H27A H 0.5367 -0.1343 0.0988 0.021 Uiso 1 1 calc R . .
H27B H 0.4021 -0.0091 0.1037 0.021 Uiso 1 1 calc R . .
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'
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
C12 P1 C27 109.18(6) . . ?
C12 P1 C1 104.21(6) . . ?
C27 P1 C1 101.99(6) . . ?
C2 C1 P1 109.97(9) . . ?
C3 C2 C11 118.62(13) . . ?
C3 C2 C1 122.49(12) . . ?
C11 C2 C1 118.88(12) . . ?
C2 C3 C4 121.87(13) . . ?
C9 C4 C5 118.65(13) . . ?
C9 C4 C3 118.68(12) . . ?
C5 C4 C3 122.66(14) . . ?
C6 C5 C4 120.90(15) . . ?
C5 C6 C7 120.40(14) . . ?
C8 C7 C6 120.40(14) . . ?
C7 C8 C9 120.34(15) . . ?
C4 C9 C10 118.72(13) . . ?
C4 C9 C8 119.30(13) . . ?
C10 C9 C8 121.96(14) . . ?
C11 C10 C9 120.96(13) . . ?
C10 C11 C2 121.13(13) . . ?
C17 C12 C13 118.41(11) . . ?
C17 C12 P1 127.04(10) . . ?
C13 C12 P1 114.36(9) . . ?
C14 C13 C12 119.25(12) . . ?
C14 C13 C18 117.18(11) . . ?
C12 C13 C18 123.53(11) . . ?
C15 C14 C13 122.76(12) . . ?
C16 C15 C14 117.35(12) . . ?
C16 C15 C21 123.46(12) . . ?
C14 C15 C21 119.11(12) . . ?
C15 C16 C17 122.37(12) . . ?
C16 C17 C12 119.45(12) . . ?
C16 C17 C24 116.92(11) . . ?
C12 C17 C24 123.63(11) . . ?
C19 C18 C13 111.91(11) . . ?
C19 C18 C20 111.19(12) . . ?
C13 C18 C20 110.68(11) . . ?
C15 C21 C22 113.97(11) . . ?
C15 C21 C23 109.96(10) . . ?
C22 C21 C23 111.20(11) . . ?
C17 C24 C25 111.87(11) . . ?
C17 C24 C26 110.68(11) . . ?
C25 C24 C26 110.68(11) . . ?
C27 C27 P1 107.76(12) 2_655 . ?
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 C12 1.8524(13) . ?
P1 C27 1.8542(13) . ?
P1 C1 1.8610(13) . ?
C1 C2 1.5071(19) . ?
C2 C3 1.3678(19) . ?
C2 C11 1.423(2) . ?
C3 C4 1.425(2) . ?
C4 C9 1.417(2) . ?
C4 C5 1.416(2) . ?
C5 C6 1.369(2) . ?
C6 C7 1.406(3) . ?
C7 C8 1.370(2) . ?
C8 C9 1.422(2) . ?
C9 C10 1.419(2) . ?
C10 C11 1.363(2) . ?
C12 C17 1.4137(18) . ?
C12 C13 1.4198(18) . ?
C13 C14 1.3950(18) . ?
C13 C18 1.5260(18) . ?
C14 C15 1.3860(19) . ?
C15 C16 1.3901(18) . ?
C15 C21 1.5233(17) . ?
C16 C17 1.3996(18) . ?
C17 C24 1.5284(18) . ?
C18 C19 1.527(2) . ?
C18 C20 1.5333(19) . ?
C21 C22 1.5257(19) . ?
C21 C23 1.5319(18) . ?
C24 C25 1.5321(19) . ?
C24 C26 1.5364(18) . ?
C27 C27 1.548(2) 2_655 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139097036
