#------------------------------------------------------------------------------
#$Date: 2016-03-22 22:00:52 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179030 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/28/4122822.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_4122822
loop_
_publ_author_name
'Molitor, Sebastian'
'Becker, Julia'
'Gessner, Viktoria H.'
_publ_section_title
;
 Selective dehydrocoupling of phosphines by lithium chloride carbenoids.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15517
_journal_page_last               15520
_journal_paper_doi               10.1021/ja509381w
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C28 H28 O4 P2'
_chemical_formula_weight         490.44
_chemical_name_systematic
;
 ?
;
_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_date             2014-04-10T17:47:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 107.496(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.4088(15)
_cell_length_b                   6.4226(4)
_cell_length_c                   16.4976(10)
_cell_measurement_temperature    100(2)
_cell_volume                     2466.6(3)
_computing_cell_refinement       'SAINTPLUS 8.18C (Bruker APEX2, 2011)'
_computing_data_collection       'SMART 5.622 (Bruker AXS, 2001)'
_computing_data_reduction        'SAINTPLUS 8.18C (Bruker APEX2, 2011)'
_computing_molecular_graphics    'Ortep-3 V1.08 (Farrugia, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-CCD'
_diffrn_measurement_method       omega-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13801
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs 2008 (Bruker AXS, 2008)'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0478P)²+2.4165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0834
_reflns_number_gt                1970
_reflns_number_total             2163
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja509381w_si_003.cif
_cod_data_source_block           sad
_cod_depositor_comments
'Adding full bibliography for 4122822--4122824.cif.'
_cod_original_sg_symbol_H-M      C2/C
_cod_database_code               4122822
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
P1 P 0.274845(16) 0.23013(6) 0.56908(2) 0.01443(13) Uani 1 1 d .
O1 O 0.48757(5) 0.71451(17) 0.57835(8) 0.0269(3) Uani 1 1 d .
O2 O 0.11571(5) 0.70276(17) 0.71732(7) 0.0216(3) Uani 1 1 d .
C1 C 0.33690(6) 0.3962(2) 0.57167(9) 0.0154(3) Uani 1 1 d .
C2 C 0.37932(6) 0.3119(2) 0.53968(10) 0.0200(3) Uani 1 1 d .
H2 H 0.3741 0.1766 0.5153 0.024 Uiso 1 1 calc R
C3 C 0.42857(7) 0.4222(2) 0.54298(10) 0.0216(4) Uani 1 1 d .
H3 H 0.4565 0.3633 0.5201 0.026 Uiso 1 1 calc R
C4 C 0.43742(6) 0.6193(2) 0.57968(9) 0.0185(3) Uani 1 1 d .
C5 C 0.39676(7) 0.7057(2) 0.61279(10) 0.0201(3) Uani 1 1 d .
H5 H 0.4028 0.8393 0.6387 0.024 Uiso 1 1 calc R
C6 C 0.34673(6) 0.5935(2) 0.60761(9) 0.0187(3) Uani 1 1 d .
H6 H 0.3185 0.6542 0.6294 0.022 Uiso 1 1 calc R
C7 C 0.50247(8) 0.9062(3) 0.62059(15) 0.0431(5) Uani 1 1 d .
H7A H 0.5392 0.9541 0.6147 0.065 Uiso 1 1 calc R
H7B H 0.506 0.8887 0.681 0.065 Uiso 1 1 calc R
H7C H 0.4726 1.0093 0.5955 0.065 Uiso 1 1 calc R
C8 C 0.22991(6) 0.3951(2) 0.61422(9) 0.0147(3) Uani 1 1 d .
C9 C 0.20866(6) 0.5906(2) 0.58312(9) 0.0171(3) Uani 1 1 d .
H9 H 0.2206 0.6506 0.5385 0.02 Uiso 1 1 calc R
C10 C 0.17064(6) 0.7009(2) 0.61527(9) 0.0170(3) Uani 1 1 d .
H10 H 0.1569 0.8339 0.5931 0.02 Uiso 1 1 calc R
C11 C 0.15311(6) 0.6125(2) 0.68056(9) 0.0159(3) Uani 1 1 d .
C12 C 0.17398(6) 0.4187(2) 0.71282(9) 0.0179(3) Uani 1 1 d .
H12 H 0.1622 0.3595 0.7577 0.021 Uiso 1 1 calc R
C13 C 0.21180(6) 0.3109(2) 0.68021(9) 0.0160(3) Uani 1 1 d .
H13 H 0.2256 0.1783 0.7029 0.019 Uiso 1 1 calc R
C14 C 0.08799(7) 0.8901(3) 0.68036(11) 0.0263(4) Uani 1 1 d .
H14A H 0.1168 0.9992 0.6849 0.04 Uiso 1 1 calc R
H14B H 0.0609 0.9342 0.7104 0.04 Uiso 1 1 calc R
H14C H 0.0671 0.8658 0.6204 0.04 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_3
C8 P1 C1 104.11(7) .
C8 P1 P1 98.02(5) 7_556
C1 P1 P1 98.44(5) 7_556
C4 O1 C7 118.68(13) .
C11 O2 C14 117.56(12) .
C6 C1 C2 117.37(13) .
C6 C1 P1 124.99(11) .
C2 C1 P1 117.52(11) .
C3 C2 C1 121.23(14) .
C2 C3 C4 120.17(14) .
O1 C4 C5 125.12(14) .
O1 C4 C3 114.85(13) .
C5 C4 C3 120.02(14) .
C4 C5 C6 119.05(14) .
C1 C6 C5 122.15(14) .
C9 C8 C13 117.64(13) .
C9 C8 P1 124.83(11) .
C13 C8 P1 117.32(11) .
C10 C9 C8 122.25(13) .
C9 C10 C11 118.81(14) .
O2 C11 C12 115.26(13) .
O2 C11 C10 124.84(14) .
C12 C11 C10 119.90(13) .
C13 C12 C11 120.64(13) .
C12 C13 C8 120.76(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C8 1.8362(14) .
P1 C1 1.8423(15) .
P1 P1 2.2514(7) 7_556
O1 C4 1.3746(18) .
O1 C7 1.407(2) .
O2 C11 1.3674(17) .
O2 C14 1.4245(19) .
C1 C6 1.389(2) .
C1 C2 1.404(2) .
C2 C3 1.382(2) .
C3 C4 1.392(2) .
C4 C5 1.385(2) .
C5 C6 1.398(2) .
C8 C9 1.396(2) .
C8 C13 1.401(2) .
C9 C10 1.393(2) .
C10 C11 1.394(2) .
C11 C12 1.389(2) .
C12 C13 1.386(2) .
