#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:41:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178529 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/34/4063440.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_4063440
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_moiety         'C54 H68 O2 P2, (C3 H8 O) '
_chemical_formula_sum            'C57 H76 O3 P2'
_chemical_formula_weight         871.12
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
SHELXL-97

Program PLATON SQUEEZE used to fit unrefined solvent. Program found
143 e/unit cell with void volume of 550 angstroms3. Associated with
4 molecules of isopropyl alcohol CH3-CHOH-CH3 or 146 e. The four
molecules of CH3CHOHCH3 included in the chemical formula unit card to
account for density, molecular mass and F000.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.474(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.621(5)
_cell_length_b                   11.064(3)
_cell_length_c                   21.618(5)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.46
_cell_volume                     5035(2)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            28045
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.201
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         5826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0970P)²+4.4203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1842
_refine_ls_wR_factor_ref         0.1963
_reflns_number_gt                4414
_reflns_number_total             5826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900800z_si_002.cif
_cod_data_source_block           glu319
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      C2/c
_cod_database_code               4063440
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.07527(2) 0.37339(5) 0.55550(3) 0.02607(17) Uani 1 1 d . . .
O1 O 0.05401(7) 0.37246(15) 0.61313(8) 0.0339(4) Uani 1 1 d . . .
C1 C 0.03463(9) 0.49692(19) 0.50098(11) 0.0277(5) Uani 1 1 d . . .
H1A H 0.0568 0.5741 0.5178 0.033 Uiso 1 1 calc R . .
H1B H 0.0345 0.4831 0.4557 0.033 Uiso 1 1 calc R . .
C2 C 0.05072(11) 0.23797(19) 0.50475(11) 0.0332(5) Uani 1 1 d . . .
H2A H 0.0044 0.2423 0.4792 0.040 Uiso 1 1 calc R . .
H2B H 0.0725 0.2358 0.4725 0.040 Uiso 1 1 calc R . .
C3 C 0.06507(11) 0.1228(2) 0.54452(12) 0.0343(5) Uani 1 1 d . . .
C4 C 0.10976(12) 0.0425(2) 0.54178(12) 0.0376(5) Uani 1 1 d . . .
H4A H 0.1349 0.0615 0.5162 0.045 Uiso 1 1 calc R . .
C5 C 0.11953(11) -0.0712(2) 0.57729(12) 0.0380(6) Uani 1 1 d . . .
C6 C 0.16355(14) -0.1578(2) 0.57243(14) 0.0485(7) Uani 1 1 d . . .
H6A H 0.1891 -0.1406 0.5471 0.058 Uiso 1 1 calc R . .
C7 C 0.16919(15) -0.2667(3) 0.60437(15) 0.0559(8) Uani 1 1 d . . .
H7A H 0.1989 -0.3247 0.6011 0.067 Uiso 1 1 calc R . .
C8 C 0.13130(15) -0.2937(2) 0.64203(14) 0.0539(8) Uani 1 1 d . . .
H8A H 0.1351 -0.3701 0.6631 0.065 Uiso 1 1 calc R . .
C9 C 0.08974(15) -0.2117(3) 0.64823(14) 0.0518(7) Uani 1 1 d . . .
H9A H 0.0649 -0.2305 0.6741 0.062 Uiso 1 1 calc R . .
C10 C 0.08273(12) -0.0957(2) 0.61587(13) 0.0412(6) Uani 1 1 d . . .
C11 C 0.03826(14) -0.0101(3) 0.61989(16) 0.0503(7) Uani 1 1 d . . .
H11A H 0.0143 -0.0260 0.6471 0.060 Uiso 1 1 calc R . .
C12 C 0.02928(12) 0.0955(2) 0.58505(14) 0.0441(6) Uani 1 1 d . . .
H12A H -0.0014 0.1518 0.5878 0.053 Uiso 1 1 calc R . .
C13 C 0.16189(9) 0.38821(18) 0.58014(11) 0.0266(4) Uani 1 1 d . . .
C14 C 0.19101(10) 0.43615(19) 0.53747(11) 0.0315(5) Uani 1 1 d . . .
C15 C 0.25566(11) 0.4684(2) 0.56472(14) 0.0388(6) Uani 1 1 d . . .
H15A H 0.2748 0.5028 0.5364 0.047 Uiso 1 1 calc R . .
C16 C 0.29245(11) 0.4518(2) 0.63142(14) 0.0408(6) Uani 1 1 d . . .
C17 C 0.26449(11) 0.3936(2) 0.67043(13) 0.0368(5) Uani 1 1 d . . .
H17A H 0.2899 0.3762 0.7154 0.044 Uiso 1 1 calc R . .
C18 C 0.20082(10) 0.3594(2) 0.64680(11) 0.0315(5) Uani 1 1 d . . .
C19 C 0.17959(11) 0.2860(2) 0.69481(11) 0.0384(6) Uani 1 1 d . . .
H19A H 0.1340 0.2641 0.6711 0.046 Uiso 1 1 calc R . .
C20 C 0.21794(13) 0.1678(2) 0.71293(13) 0.0447(6) Uani 1 1 d . . .
H20A H 0.2124 0.1223 0.6723 0.067 Uiso 1 1 calc R . .
H20B H 0.2029 0.1192 0.7421 0.067 Uiso 1 1 calc R . .
H20C H 0.2630 0.1867 0.7359 0.067 Uiso 1 1 calc R . .
C21 C 0.18424(15) 0.3596(3) 0.75659(13) 0.0541(8) Uani 1 1 d . . .
H21A H 0.1565 0.4304 0.7431 0.081 Uiso 1 1 calc R . .
H21B H 0.2282 0.3860 0.7796 0.081 Uiso 1 1 calc R . .
H21C H 0.1710 0.3092 0.7865 0.081 Uiso 1 1 calc R . .
C22 C 0.15785(11) 0.4508(2) 0.46206(12) 0.0348(5) Uani 1 1 d . . .
H22A H 0.1139 0.4175 0.4492 0.042 Uiso 1 1 calc R . .
C23 C 0.15233(13) 0.5833(2) 0.44002(13) 0.0424(6) Uani 1 1 d . . .
H23A H 0.1304 0.6294 0.4639 0.064 Uiso 1 1 calc R . .
H23B H 0.1282 0.5884 0.3921 0.064 Uiso 1 1 calc R . .
H23C H 0.1949 0.6170 0.4500 0.064 Uiso 1 1 calc R . .
C24 C 0.19266(14) 0.3773(3) 0.42555(15) 0.0507(7) Uani 1 1 d . . .
H24A H 0.1966 0.2931 0.4406 0.076 Uiso 1 1 calc R . .
H24B H 0.2351 0.4115 0.4351 0.076 Uiso 1 1 calc R . .
H24C H 0.1685 0.3804 0.3776 0.076 Uiso 1 1 calc R . .
C25 C 0.36234(13) 0.4880(3) 0.6632(2) 0.0628(9) Uani 1 1 d . . .
H25A H 0.3666 0.5139 0.7090 0.075 Uiso 1 1 calc R . .
C26 C 0.37859(15) 0.6007(3) 0.63401(15) 0.0551(8) Uani 1 1 d . . .
H26A H 0.4202 0.6305 0.6633 0.083 Uiso 1 1 calc R . .
H26B H 0.3463 0.6626 0.6296 0.083 Uiso 1 1 calc R . .
H26C H 0.3798 0.5824 0.5901 0.083 Uiso 1 1 calc R . .
C27 C 0.40456(15) 0.3820(4) 0.6755(2) 0.0818(13) Uani 1 1 d . . .
H27A H 0.4469 0.4038 0.7071 0.123 Uiso 1 1 calc R . .
H27B H 0.4077 0.3555 0.6336 0.123 Uiso 1 1 calc R . .
H27C H 0.3872 0.3163 0.6941 0.123 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'
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 107.79(10) . . ?
O1 P1 C2 112.18(11) . . ?
C1 P1 C2 104.93(10) . . ?
O1 P1 C13 113.19(10) . . ?
C1 P1 C13 110.65(10) . . ?
C2 P1 C13 107.79(10) . . ?
C1 C1 P1 108.43(19) 5_566 . ?
C1 C1 H1A 110.0 5_566 . ?
P1 C1 H1A 110.0 . . ?
C1 C1 H1B 110.0 5_566 . ?
P1 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C3 C2 P1 113.47(16) . . ?
C3 C2 H2A 108.9 . . ?
P1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
P1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C12 119.0(2) . . ?
C4 C3 C2 122.4(2) . . ?
C12 C3 C2 118.6(2) . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C10 C5 C6 120.0(2) . . ?
C10 C5 C4 118.3(2) . . ?
C6 C5 C4 121.7(3) . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 119.6 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C5 C10 C11 120.0(2) . . ?
C5 C10 C9 118.4(3) . . ?
C11 C10 C9 121.5(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C3 121.2(3) . . ?
C11 C12 H12A 119.4 . . ?
C3 C12 H12A 119.4 . . ?
C14 C13 C18 118.68(19) . . ?
C14 C13 P1 122.95(16) . . ?
C18 C13 P1 118.16(17) . . ?
C15 C14 C13 118.8(2) . . ?
C15 C14 C22 116.5(2) . . ?
C13 C14 C22 124.6(2) . . ?
C16 C15 C14 122.5(2) . . ?
C16 C15 H15A 118.8 . . ?
C14 C15 H15A 118.8 . . ?
C17 C16 C15 117.4(2) . . ?
C17 C16 C25 118.4(3) . . ?
C15 C16 C25 124.1(3) . . ?
C16 C17 C18 123.0(2) . . ?
C16 C17 H17A 118.5 . . ?
C18 C17 H17A 118.5 . . ?
C17 C18 C13 119.0(2) . . ?
C17 C18 C19 115.8(2) . . ?
C13 C18 C19 125.1(2) . . ?
C18 C19 C21 111.8(2) . . ?
C18 C19 C20 109.7(2) . . ?
C21 C19 C20 112.1(2) . . ?
C18 C19 H19A 107.7 . . ?
C21 C19 H19A 107.7 . . ?
C20 C19 H19A 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C14 112.6(2) . . ?
C23 C22 C24 110.2(2) . . ?
C14 C22 C24 110.3(2) . . ?
C23 C22 H22A 107.9 . . ?
C14 C22 H22A 107.9 . . ?
C24 C22 H22A 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C27 C25 C26 119.6(3) . . ?
C27 C25 C16 111.6(3) . . ?
C26 C25 C16 113.6(3) . . ?
C27 C25 H25A 103.2 . . ?
C26 C25 H25A 103.2 . . ?
C16 C25 H25A 103.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 O1 1.4906(17) . ?
P1 C1 1.819(2) . ?
P1 C2 1.820(2) . ?
P1 C13 1.840(2) . ?
C1 C1 1.553(4) 5_566 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.504(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.363(3) . ?
C3 C12 1.426(4) . ?
C4 C5 1.448(3) . ?
C4 H4A 0.9500 . ?
C5 C10 1.404(4) . ?
C5 C6 1.413(4) . ?
C6 C7 1.372(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.413(5) . ?
C7 H7A 0.9500 . ?
C8 C9 1.348(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.442(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.407(4) . ?
C11 C12 1.364(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.418(3) . ?
C13 C18 1.423(3) . ?
C14 C15 1.408(3) . ?
C14 C22 1.533(3) . ?
C15 C16 1.388(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.384(4) . ?
C16 C25 1.529(3) . ?
C17 C18 1.393(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.527(3) . ?
C19 C21 1.534(4) . ?
C19 C20 1.539(4) . ?
C19 H19A 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.533(3) . ?
C22 C24 1.536(3) . ?
C22 H22A 1.0000 . ?
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 C27 1.474(5) . ?
C25 C26 1.502(4) . ?
C25 H25A 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
