#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:15:32 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178599 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/10/4071092.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_4071092
loop_
_publ_author_name
'Escobar, Aholibama'
'Donnadieu, Bruno'
'Mathey, François'
_publ_section_title
;
 From Functional Phospholide Ions to Bifunctional
 1,1′-Diphosphaferrocenes
;
_journal_issue                   8
_journal_name_full               Organometallics
_journal_page_first              1887
_journal_paper_doi               10.1021/om7012474
_journal_volume                  27
_journal_year                    2008
_chemical_formula_moiety         'C12 H16 O4 P'
_chemical_formula_sum            'C12 H16 O4 P'
_chemical_formula_weight         255.22
_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                 109.335(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.816(5)
_cell_length_b                   10.489(2)
_cell_length_c                   12.513(3)
_cell_measurement_reflns_used    3590
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.71
_cell_measurement_theta_min      2.20
_cell_volume                     2578.0(10)
_computing_cell_refinement       'Bruker APEX 2.02'
_computing_data_collection       'Bruker APEX 2.02'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6858
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.8844
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.105
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0506P)²+5.7561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                1617
_reflns_number_total             1835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om7012474-file001.cif
_cod_data_source_block           6
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2578.2(10)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4071092
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 0.00901(3) 0.96997(6) 0.66703(5) 0.0185(2) Uani 1 1 d .
O1 O 0.12179(10) 1.28570(18) 0.74261(18) 0.0402(5) Uani 1 1 d .
O2 O 0.15040(8) 1.08022(16) 0.73727(14) 0.0243(4) Uani 1 1 d .
O3 O -0.19078(9) 0.9325(2) 0.49593(16) 0.0384(5) Uani 1 1 d .
O4 O -0.10686(9) 0.80440(17) 0.59935(16) 0.0329(5) Uani 1 1 d .
C1 C -0.07623(12) 1.0110(2) 0.5775(2) 0.0213(6) Uani 1 1 d .
C2 C -0.07936(12) 1.1314(2) 0.5361(2) 0.0232(6) Uani 1 1 d .
C3 C -0.01464(13) 1.2002(2) 0.5806(2) 0.0223(6) Uani 1 1 d .
C4 C 0.03586(12) 1.1316(2) 0.65586(19) 0.0187(5) Uani 1 1 d .
C5 C 0.10557(13) 1.1768(2) 0.7150(2) 0.0244(6) Uani 1 1 d .
C6 C 0.22096(13) 1.1146(3) 0.7960(2) 0.0315(7) Uani 1 1 d .
H6A H 0.2265 1.1448 0.8735 0.038 Uiso 1 1 calc R
H6B H 0.2352 1.1838 0.7549 0.038 Uiso 1 1 calc R
C7 C 0.26342(14) 0.9988(3) 0.8010(2) 0.0360(7) Uani 1 1 d .
H7A H 0.2471 0.9292 0.8376 0.054 Uiso 1 1 calc R
H7B H 0.3110 1.0177 0.8447 0.054 Uiso 1 1 calc R
H7C H 0.2601 0.9733 0.7240 0.054 Uiso 1 1 calc R
C8 C -0.13171(13) 0.9163(3) 0.5508(2) 0.0259(6) Uani 1 1 d .
C9 C -0.15472(17) 0.6994(3) 0.5833(3) 0.0459(8) Uani 1 1 d .
H9A H -0.1741 0.6772 0.5020 0.055 Uiso 1 1 calc R
H9B H -0.1924 0.7231 0.6111 0.055 Uiso 1 1 calc R
C10 C -0.11596(19) 0.5895(3) 0.6491(4) 0.0611(11) Uani 1 1 d .
H10A H -0.0763 0.5722 0.6256 0.092 Uiso 1 1 calc R
H10B H -0.1454 0.5141 0.6349 0.092 Uiso 1 1 calc R
H10C H -0.1007 0.6099 0.7301 0.092 Uiso 1 1 calc R
C11 C -0.14010(14) 1.1939(3) 0.4533(2) 0.0351(7) Uani 1 1 d .
H11A H -0.1795 1.1370 0.4373 0.053 Uiso 1 1 calc R
H11B H -0.1308 1.2118 0.3830 0.053 Uiso 1 1 calc R
H11C H -0.1498 1.2739 0.4855 0.053 Uiso 1 1 calc R
C12 C -0.00765(15) 1.3325(2) 0.5396(3) 0.0355(7) Uani 1 1 d .
H12A H 0.0391 1.3627 0.5759 0.053 Uiso 1 1 calc R
H12B H -0.0393 1.3898 0.5590 0.053 Uiso 1 1 calc R
H12C H -0.0182 1.3313 0.4573 0.053 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_3
C4 P1 C1 89.66(11) .
C4 P1 P1 102.95(8) 2_556
C1 P1 P1 98.29(9) 2_556
C5 O2 C6 115.7(2) .
C8 O4 C9 117.1(2) .
C2 C1 C8 127.2(2) .
C2 C1 P1 111.75(19) .
C8 C1 P1 120.90(19) .
C1 C2 C3 113.0(2) .
C1 C2 C11 126.5(2) .
C3 C2 C11 120.5(2) .
C4 C3 C2 113.9(2) .
C4 C3 C12 125.7(2) .
C2 C3 C12 120.4(2) .
C3 C4 C5 125.8(2) .
C3 C4 P1 111.20(18) .
C5 C4 P1 122.83(18) .
O1 C5 O2 123.0(2) .
O1 C5 C4 125.7(2) .
O2 C5 C4 111.3(2) .
O2 C6 C7 107.7(2) .
O3 C8 O4 123.3(2) .
O3 C8 C1 127.4(3) .
O4 C8 C1 109.3(2) .
O4 C9 C10 106.8(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C4 1.805(2) .
P1 C1 1.809(2) .
P1 P1 2.2289(14) 2_556
O1 C5 1.209(3) .
O2 C5 1.342(3) .
O2 C6 1.454(3) .
O3 C8 1.206(3) .
O4 C8 1.343(3) .
O4 C9 1.454(3) .
C1 C2 1.358(4) .
C1 C8 1.475(4) .
C2 C3 1.466(4) .
C2 C11 1.494(3) .
C3 C4 1.362(3) .
C3 C12 1.503(4) .
C4 C5 1.472(3) .
C6 C7 1.491(4) .
C9 C10 1.489(5) .
