#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:49:05 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179457 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/54/4335404.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_4335404
loop_
_publ_author_name
'Philip J. W. Elder'
'Tristram Chivers'
_publ_section_title
;
 Chalcogenation of the 1,4-C2P4 Ring: Oxidation, Isomerization, Insertion,
 and Ring Contraction
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7791
_journal_page_last               7804
_journal_paper_doi               10.1021/ic401002b
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C18 H40 P4'
_chemical_formula_sum            'C18 H40 P4'
_chemical_formula_weight         380.38
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.024(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0430(11)
_cell_length_b                   12.5350(10)
_cell_length_c                   11.6060(6)
_cell_measurement_reflns_used    4279
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.3
_cell_measurement_theta_min      2.1
_cell_volume                     2282.7(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        DENZO-SMN
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'KappaCCD (Nonius, FR540C)'
_diffrn_measurement_method       'phiω scans'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'Enraf Nonius FR590D, fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4279
_diffrn_reflns_theta_full        30.26
_diffrn_reflns_theta_max         30.26
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.9617
_exptl_absorpt_correction_T_min  0.9254
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (SHELXTL-NT v5.1, Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.244
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.244
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0539
_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)+(0.0791P)²+2.5408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1729
_reflns_number_gt                2895
_reflns_number_total             3319
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ic401002b_si_003_1.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4335404
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 0.05336(4) 0.12763(5) 0.60866(5) 0.03164(17) Uani 1 1 d .
P2 P -0.11896(3) 0.16525(4) 0.70884(5) 0.03118(17) Uani 1 1 d .
C6 C -0.0259(2) 0.2428(3) 0.4172(2) 0.0559(7) Uani 1 1 d .
H6A H -0.0088 0.1836 0.3752 0.084 Uiso 1 1 calc R
H6B H -0.0296 0.3059 0.3695 0.084 Uiso 1 1 calc R
H6C H -0.0806 0.2282 0.4351 0.084 Uiso 1 1 calc R
C7 C -0.21547(14) 0.0760(2) 0.6936(2) 0.0374(5) Uani 1 1 d .
C3 C 0.03927(15) 0.2600(2) 0.5311(2) 0.0372(5) Uani 1 1 d .
C1 C -0.05355(14) 0.08569(19) 0.6257(2) 0.0354(4) Uani 1 1 d .
H1A H -0.0471 0.0154 0.6615 0.042 Uiso 1 1 calc R
H1B H -0.0876 0.0765 0.5468 0.042 Uiso 1 1 calc R
C9 C -0.27070(17) 0.1216(2) 0.7740(2) 0.0463(6) Uani 1 1 d .
H9A H -0.2403 0.1175 0.8544 0.069 Uiso 1 1 calc R
H9B H -0.3225 0.0812 0.7647 0.069 Uiso 1 1 calc R
H9C H -0.2840 0.1947 0.7535 0.069 Uiso 1 1 calc R
C5 C 0.0121(2) 0.3533(2) 0.5978(2) 0.0475(6) Uani 1 1 d .
H5A H -0.0418 0.3377 0.6175 0.071 Uiso 1 1 calc R
H5B H 0.0069 0.4161 0.5495 0.071 Uiso 1 1 calc R
H5C H 0.0540 0.3653 0.6688 0.071 Uiso 1 1 calc R
C4 C 0.12535(19) 0.2854(2) 0.5016(3) 0.0513(6) Uani 1 1 d .
H4A H 0.1432 0.2264 0.4598 0.077 Uiso 1 1 calc R
H4B H 0.1667 0.2975 0.5731 0.077 Uiso 1 1 calc R
H4C H 0.1204 0.3482 0.4533 0.077 Uiso 1 1 calc R
C8 C -0.19583(18) -0.0403(2) 0.7264(3) 0.0493(6) Uani 1 1 d .
H8A H -0.1656 -0.0446 0.8069 0.074 Uiso 1 1 calc R
H8B H -0.1614 -0.0699 0.6760 0.074 Uiso 1 1 calc R
H8C H -0.2481 -0.0797 0.7171 0.074 Uiso 1 1 calc R
C10 C -0.26382(18) 0.0847(3) 0.5656(2) 0.0523(7) Uani 1 1 d .
H10A H -0.2295 0.0559 0.5144 0.078 Uiso 1 1 calc R
H10B H -0.2761 0.1583 0.5463 0.078 Uiso 1 1 calc R
H10C H -0.3162 0.0455 0.5557 0.078 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_3
C1 P1 C3 106.35(11) .
C1 P1 P2 103.06(7) 2_556
C3 P1 P2 104.85(8) 2_556
C1 P2 C7 100.03(10) .
C1 P2 P1 100.11(8) 2_556
C7 P2 P1 100.40(8) 2_556
C3 C6 H6A 109.5 .
C3 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
C3 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
C8 C7 C9 108.8(2) .
C8 C7 C10 110.4(2) .
C9 C7 C10 109.0(2) .
C8 C7 P2 114.89(17) .
C9 C7 P2 106.86(17) .
C10 C7 P2 106.74(17) .
C5 C3 C6 109.5(2) .
C5 C3 C4 108.9(2) .
C6 C3 C4 109.0(2) .
C5 C3 P1 117.10(16) .
C6 C3 P1 106.47(18) .
C4 C3 P1 105.52(18) .
P1 C1 P2 122.79(12) .
P1 C1 H1A 106.6 .
P2 C1 H1A 106.6 .
P1 C1 H1B 106.6 .
P2 C1 H1B 106.6 .
H1A C1 H1B 106.6 .
C7 C9 H9A 109.5 .
C7 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
C7 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
C3 C5 H5A 109.5 .
C3 C5 H5B 109.5 .
H5A C5 H5B 109.5 .
C3 C5 H5C 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
C3 C4 H4A 109.5 .
C3 C4 H4B 109.5 .
H4A C4 H4B 109.5 .
C3 C4 H4C 109.5 .
H4A C4 H4C 109.5 .
H4B C4 H4C 109.5 .
C7 C8 H8A 109.5 .
C7 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C7 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C7 C10 H10A 109.5 .
C7 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
C7 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C1 1.843(2) .
P1 C3 1.879(2) .
P1 P2 2.2107(8) 2_556
P2 C1 1.857(2) .
P2 C7 1.889(2) .
P2 P1 2.2107(8) 2_556
C6 C3 1.520(4) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 C8 1.522(4) .
C7 C9 1.525(3) .
C7 C10 1.530(4) .
C3 C5 1.516(4) .
C3 C4 1.524(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
