#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:51:50 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179458 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/55/4335597.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_4335597
loop_
_publ_author_name
'Daniel Tofan'
'Manuel Temprado'
'Subhojit Majumdar'
'Carl D. Hoff'
'Christopher C. Cummins'
_publ_section_title
;
 Functionalization Reactions Characteristic of a Robust Bicyclic
 Diphosphane Framework
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8851
_journal_page_last               8864
_journal_paper_doi               10.1021/ic401052a
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C12 H20 O3 P2'
_chemical_formula_weight         274.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.956(2)
_cell_angle_beta                 98.939(2)
_cell_angle_gamma                101.833(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6898(6)
_cell_length_b                   8.1011(6)
_cell_length_c                   10.7689(8)
_cell_measurement_reflns_used    9813
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.45
_cell_measurement_theta_min      2.58
_cell_volume                     645.09(8)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2010)'
_computing_data_collection       'APEX2 v2010.7.0 (Bruker-AXS, 2010)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2010)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Incoatech ImuS multilayer optics'
_diffrn_radiation_source         'ImuS micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42402
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.9613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.779
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3904
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0531
_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)+(0.0758P)²+0.4523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1502
_reflns_number_gt                3433
_reflns_number_total             3904
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic401052a_si_006.cif
_cod_data_source_block           x8_10087
_cod_database_code               4335597
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.53608(6) 0.44562(6) 0.27286(5) 0.01996(14) Uani 1 1 d U . .
P2 P 0.78915(14) 0.49961(7) 0.09525(7) 0.01791(19) Uani 0.832(3) 1 d PU A 1
O1 O 0.3995(6) 0.5415(7) 0.3101(4) 0.0250(5) Uani 0.832(3) 1 d P A 1
O2 O 0.8333(2) 0.6314(2) 0.00970(16) 0.0242(4) Uani 0.832(3) 1 d P A 1
O3 O 0.6268(2) 0.53469(19) 0.16381(15) 0.0195(4) Uani 0.832(3) 1 d P A 1
C4 C 0.69271(19) 0.28704(16) 0.01878(13) 0.0269(4) Uani 1 1 d . . .
H4A H 0.5663 0.2809 -0.0212 0.032 Uiso 0.832(3) 1 calc PR A 1
H4B H 0.7605 0.2635 -0.0490 0.032 Uiso 0.832(3) 1 calc PR A 1
H4A1 H 0.5778 0.2616 -0.0421 0.032 Uiso 0.168(3) 1 calc PR A 2
H4A2 H 0.7939 0.2947 -0.0288 0.032 Uiso 0.168(3) 1 calc PR A 2
C5 C 0.96474(19) 0.49968(16) 0.22379(13) 0.0209(3) Uani 1 1 d RU . .
H5A H 0.9437 0.3879 0.2573 0.025 Uiso 0.832(3) 1 calc PR A 1
H5B H 1.0813 0.5166 0.1930 0.025 Uiso 0.832(3) 1 calc PR A 1
H5A1 H 0.9723 0.3899 0.2569 0.025 Uiso 0.168(3) 1 calc PR A 2
H5A2 H 1.0606 0.5312 0.1727 0.025 Uiso 0.168(3) 1 calc PR A 2
P2A P 0.7161(6) 0.4917(3) 0.1227(3) 0.0178(8) Uani 0.168(3) 1 d PU A 2
O1A O 0.428(3) 0.543(4) 0.283(2) 0.035(4) Uani 0.168(3) 1 d PU A 2
O2A O 0.7157(14) 0.6426(11) 0.0574(10) 0.034(2) Uani 0.168(3) 1 d PU A 2
C1 C 0.4431(2) 0.2284(2) 0.20581(19) 0.0231(4) Uani 1 1 d . A .
H1A H 0.3601 0.1723 0.2595 0.028 Uiso 1 1 calc R . .
H1B H 0.3718 0.2283 0.1209 0.028 Uiso 1 1 calc R . .
C2 C 0.5865(2) 0.1264(2) 0.19420(18) 0.0213(3) Uani 1 1 d . . .
C21 C 0.5974(3) -0.0012(3) 0.2893(2) 0.0304(4) Uani 1 1 d . A .
H21A H 0.4994 -0.1014 0.2623 0.046 Uiso 1 1 calc R . .
H21B H 0.5862 0.0496 0.3721 0.046 Uiso 1 1 calc R . .
H21C H 0.7137 -0.0345 0.2952 0.046 Uiso 1 1 calc R . .
C31 C 0.8429(3) 0.0573(3) 0.0974(3) 0.0353(5) Uani 1 1 d . . .
H31A H 0.8406 -0.0269 0.1586 0.053 Uiso 1 1 calc R A .
H31B H 0.9603 0.1372 0.1146 0.053 Uiso 1 1 calc R . .
H31C H 0.8234 -0.0003 0.0117 0.053 Uiso 1 1 calc R . .
C3 C 0.6960(3) 0.1522(2) 0.10871(18) 0.0224(3) Uani 1 1 d . A .
C6 C 0.9761(2) 0.6371(2) 0.32928(17) 0.0195(3) Uani 1 1 d . A .
C61 C 1.1199(3) 0.7940(2) 0.3283(2) 0.0253(4) Uani 1 1 d . . .
H61A H 1.1166 0.8783 0.3973 0.038 Uiso 1 1 calc R A .
H61B H 1.0981 0.8411 0.2474 0.038 Uiso 1 1 calc R . .
H61C H 1.2385 0.7649 0.3398 0.038 Uiso 1 1 calc R . .
C71 C 0.8541(3) 0.7449(2) 0.51680(19) 0.0252(4) Uani 1 1 d . A .
H71A H 0.9619 0.8369 0.5281 0.038 Uiso 1 1 calc R . .
H71B H 0.8490 0.6915 0.5955 0.038 Uiso 1 1 calc R . .
H71C H 0.7462 0.7908 0.4949 0.038 Uiso 1 1 calc R . .
C7 C 0.8620(2) 0.6148(2) 0.41215(17) 0.0194(3) Uani 1 1 d . . .
C8 C 0.7201(2) 0.4514(2) 0.40143(17) 0.0195(3) Uani 1 1 d . A .
H8A H 0.6729 0.4421 0.4817 0.023 Uiso 1 1 calc R . .
H8B H 0.7759 0.3535 0.3869 0.023 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
O1A P1 O1 12.5(11)
O1A P1 O3 96.7(10)
O1 P1 O3 109.10(17)
O1A P1 C8 119.4(14)
O1 P1 C8 112.50(19)
O3 P1 C8 105.61(8)
O1A P1 C1 118.2(14)
O1 P1 C1 115.0(2)
O3 P1 C1 104.45(9)
C8 P1 C1 109.49(8)
O1A P1 P2A 117.6(10)
O1 P1 P2A 130.01(18)
O3 P1 P2A 20.93(10)
C8 P1 P2A 94.93(10)
C1 P1 P2A 91.75(9)
O2 P2 O3 109.67(9)
O2 P2 C5 114.59(10)
O3 P2 C5 103.27(8)
O2 P2 C4 115.66(9)
O3 P2 C4 100.67(9)
C5 P2 C4 111.28(7)
P1 O3 P2 131.73(10)
C3 C4 P2 113.14(11)
C3 C4 P2A 105.18(14)
P2 C4 P2A 20.60(12)
C6 C5 P2 112.27(10)
C6 C5 P2A 101.19(14)
P2 C5 P2A 18.66(11)
O2A P2A C4 115.9(5)
O2A P2A C5 110.9(4)
C4 P2A C5 97.82(19)
O2A P2A P1 117.7(5)
C4 P2A P1 109.74(17)
C5 P2A P1 102.03(15)
C2 C1 P1 113.23(12)
C3 C2 C21 123.48(17)
C3 C2 C1 122.29(17)
C21 C2 C1 114.20(17)
C2 C3 C31 123.62(18)
C2 C3 C4 123.52(16)
C31 C3 C4 112.76(16)
C7 C6 C61 125.45(16)
C7 C6 C5 120.42(15)
C61 C6 C5 114.11(15)
C6 C7 C71 125.32(17)
C6 C7 C8 120.38(15)
C71 C7 C8 114.23(15)
C7 C8 P1 111.00(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1A 1.27(2)
P1 O1 1.513(3)
P1 O3 1.5972(16)
P1 C8 1.8103(18)
P1 C1 1.8105(19)
P1 P2A 2.289(5)
P2 O2 1.4792(18)
P2 O3 1.609(2)
P2 C5 1.7771(15)
P2 C4 1.8123(14)
C4 C3 1.511(2)
C4 P2A 1.895(3)
C5 C6 1.514(2)
C5 P2A 2.034(4)
P2A O2A 1.452(8)
C1 C2 1.522(2)
C2 C3 1.340(3)
C2 C21 1.509(3)
C31 C3 1.506(3)
C6 C7 1.342(3)
C6 C61 1.506(2)
C71 C7 1.506(2)
C7 C8 1.518(2)
