#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:47:12 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179733 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/29/7002932.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_7002932
loop_
_publ_author_name
'Ionkin, Alex S.'
'Marshall, William J.'
'Fish, Brian M.'
_publ_section_title
;
 A rearrangement of 1,1-linked four-membered rings to bicyclic
 bridgehead five-membered rings: A phosphorus turn
;
_journal_issue                   47
_journal_name_full               'Dalton Transactions'
_journal_page_first              10574
_journal_page_last               10580
_journal_paper_doi               10.1039/b916558d
_journal_year                    2009
_chemical_formula_sum            'C22 H40 O2 P2'
_chemical_formula_weight         398.48
_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                 109.681(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.140(12)
_cell_length_b                   8.856(5)
_cell_length_c                   11.564(6)
_cell_measurement_temperature    173(2)
_cell_volume                     2328(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '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  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18860
_diffrn_reflns_theta_full        26.74
_diffrn_reflns_theta_max         26.74
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ireg.plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0447
_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)+(0.0599P)²+3.1436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                1932
_reflns_number_total             2471
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b916558d.txt
_cod_data_source_block           07034
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7002932
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 0.47672(2) 0.08410(7) 0.92846(5) 0.03252(19) Uani 1 1 d . . .
O1 O 0.41153(8) -0.1500(2) 0.77679(14) 0.0487(5) Uani 1 1 d . . .
C1 C 0.41500(9) -0.0425(3) 0.84229(18) 0.0329(5) Uani 1 1 d . . .
C2 C 0.36850(8) 0.0356(2) 0.88483(17) 0.0283(4) Uani 1 1 d . . .
H2A H 0.3428 0.0962 0.8170 0.034 Uiso 1 1 calc R . .
C3 C 0.41261(8) 0.1427(2) 0.97879(17) 0.0256(4) Uani 1 1 d . . .
H3A H 0.4191 0.1074 1.0627 0.031 Uiso 1 1 calc R . .
C4 C 0.33005(9) -0.0752(2) 0.92909(18) 0.0320(5) Uani 1 1 d . . .
C5 C 0.36788(11) -0.1853(3) 1.0247(2) 0.0403(5) Uani 1 1 d . . .
H5A H 0.3429 -0.2522 1.0504 0.060 Uiso 1 1 calc R . .
H5B H 0.3926 -0.1300 1.0944 0.060 Uiso 1 1 calc R . .
H5C H 0.3919 -0.2431 0.9896 0.060 Uiso 1 1 calc R . .
C6 C 0.29069(12) -0.1640(3) 0.8173(2) 0.0540(7) Uani 1 1 d . . .
H6A H 0.2671 -0.0949 0.7568 0.081 Uiso 1 1 calc R . .
H6B H 0.2656 -0.2307 0.8427 0.081 Uiso 1 1 calc R . .
H6C H 0.3149 -0.2220 0.7828 0.081 Uiso 1 1 calc R . .
C7 C 0.29076(10) 0.0105(3) 0.9856(2) 0.0455(6) Uani 1 1 d . . .
H7A H 0.2668 0.0810 0.9267 0.068 Uiso 1 1 calc R . .
H7B H 0.3148 0.0641 1.0571 0.068 Uiso 1 1 calc R . .
H7C H 0.2659 -0.0595 1.0085 0.068 Uiso 1 1 calc R . .
C8 C 0.40278(9) 0.3158(2) 0.97147(18) 0.0296(4) Uani 1 1 d . . .
C9 C 0.45546(10) 0.3861(3) 1.0709(2) 0.0388(5) Uani 1 1 d . . .
H9A H 0.4578 0.3467 1.1497 0.058 Uiso 1 1 calc R . .
H9B H 0.4507 0.4938 1.0706 0.058 Uiso 1 1 calc R . .
H9C H 0.4909 0.3621 1.0547 0.058 Uiso 1 1 calc R . .
C10 C 0.34724(10) 0.3566(3) 0.9994(2) 0.0382(5) Uani 1 1 d . . .
H10A H 0.3506 0.3206 1.0798 0.057 Uiso 1 1 calc R . .
H10B H 0.3138 0.3105 0.9396 0.057 Uiso 1 1 calc R . .
H10C H 0.3424 0.4643 0.9965 0.057 Uiso 1 1 calc R . .
C11 C 0.39782(11) 0.3811(3) 0.84565(19) 0.0400(5) Uani 1 1 d . . .
H11A H 0.3928 0.4886 0.8465 0.060 Uiso 1 1 calc R . .
H11B H 0.3646 0.3370 0.7837 0.060 Uiso 1 1 calc R . .
H11C H 0.4330 0.3586 0.8279 0.060 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
C1 P1 C3 74.98(9) . . ?
C1 P1 P1 96.17(8) . 5_657 ?
C3 P1 P1 102.38(7) . 5_657 ?
O1 C1 C2 131.0(2) . . ?
O1 C1 P1 133.41(18) . . ?
C2 C1 P1 95.58(14) . . ?
C1 C2 C4 113.89(18) . . ?
C1 C2 C3 95.50(15) . . ?
C4 C2 C3 119.90(16) . . ?
C8 C3 C2 120.50(16) . . ?
C8 C3 P1 112.28(13) . . ?
C2 C3 P1 93.20(12) . . ?
C7 C4 C5 108.36(18) . . ?
C7 C4 C6 108.5(2) . . ?
C5 C4 C6 109.3(2) . . ?
C7 C4 C2 110.79(18) . . ?
C5 C4 C2 111.40(17) . . ?
C6 C4 C2 108.39(17) . . ?
C10 C8 C9 108.18(18) . . ?
C10 C8 C11 108.61(17) . . ?
C9 C8 C11 109.83(18) . . ?
C10 C8 C3 110.61(17) . . ?
C9 C8 C3 106.76(17) . . ?
C11 C8 C3 112.75(17) . . ?
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 C1 1.863(2) . ?
P1 C3 1.900(2) . ?
P1 P1 2.2286(13) 5_657 ?
O1 C1 1.202(3) . ?
C1 C2 1.533(3) . ?
C2 C4 1.551(3) . ?
C2 C3 1.561(3) . ?
C3 C8 1.549(3) . ?
C4 C7 1.523(3) . ?
C4 C5 1.526(3) . ?
C4 C6 1.538(3) . ?
C8 C10 1.525(3) . ?
C8 C9 1.530(3) . ?
C8 C11 1.532(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 P1 C1 O1 -173.0(2) . . . . ?
P1 P1 C1 O1 -71.8(2) 5_657 . . . ?
C3 P1 C1 C2 6.04(12) . . . . ?
P1 P1 C1 C2 107.24(12) 5_657 . . . ?
O1 C1 C2 C4 45.8(3) . . . . ?
P1 C1 C2 C4 -133.33(15) . . . . ?
O1 C1 C2 C3 172.0(2) . . . . ?
P1 C1 C2 C3 -7.14(14) . . . . ?
C1 C2 C3 C8 125.25(18) . . . . ?
C4 C2 C3 C8 -113.1(2) . . . . ?
C1 C2 C3 P1 6.98(13) . . . . ?
C4 C2 C3 P1 128.63(16) . . . . ?
C1 P1 C3 C8 -130.83(15) . . . . ?
P1 P1 C3 C8 136.02(12) 5_657 . . . ?
C1 P1 C3 C2 -5.91(11) . . . . ?
P1 P1 C3 C2 -99.07(11) 5_657 . . . ?
C1 C2 C4 C7 172.41(17) . . . . ?
C3 C2 C4 C7 60.3(2) . . . . ?
C1 C2 C4 C5 51.7(2) . . . . ?
C3 C2 C4 C5 -60.4(2) . . . . ?
C1 C2 C4 C6 -68.6(2) . . . . ?
C3 C2 C4 C6 179.30(19) . . . . ?
C2 C3 C8 C10 65.9(2) . . . . ?
P1 C3 C8 C10 174.02(13) . . . . ?
C2 C3 C8 C9 -176.65(16) . . . . ?
P1 C3 C8 C9 -68.50(18) . . . . ?
C2 C3 C8 C11 -56.0(2) . . . . ?
P1 C3 C8 C11 52.2(2) . . . . ?
