#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:34:58 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179252 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/72/4317227.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_4317227
loop_
_publ_author_name
'Andrew R. Shaffer'
'Nihal Deligonul'
'Daniel A. Scherson'
'John D. Protasiewicz'
_publ_section_title
;
 A Hybrid Lithium Oxalate-Phosphinate Salt
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10756
_journal_page_last               10758
_journal_paper_doi               10.1021/ic1018532
_journal_volume                  49
_journal_year                    2010
_chemical_formula_moiety         'C56 H58 Li2 O10 P4'
_chemical_formula_sum            'C56 H58 Li2 O10 P4'
_chemical_formula_weight         1028.78
_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                109.2240(10)
_cell_angle_beta                 107.3710(10)
_cell_angle_gamma                98.1580(10)
_cell_formula_units_Z            1
_cell_length_a                   10.6895(11)
_cell_length_b                   11.5033(12)
_cell_length_c                   12.1994(13)
_cell_measurement_reflns_used    8875
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.07
_cell_volume                     1302.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      170(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker AXS APEX II 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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14476
_diffrn_reflns_theta_full        26.88
_diffrn_reflns_theta_max         26.88
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.9692
_exptl_absorpt_correction_T_min  0.9144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'AXScale in APEX 2, (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0481
_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)+(0.0852P)²+0.6295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1530
_reflns_number_gt                4816
_reflns_number_total             5515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic1018532_si_003.cif
_cod_data_source_block           nd120909_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4317227
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 1.18704(5) 0.72211(5) 0.21635(4) 0.02684(15) Uani 1 1 d . . .
P2 P 0.80100(5) 0.27301(5) 0.11536(4) 0.02877(15) Uani 1 1 d . . .
Li1 Li 0.9003(3) 0.5037(3) 0.0454(3) 0.0311(7) Uani 1 1 d . . .
O2 O 1.08847(13) 0.60230(13) 0.11378(12) 0.0307(3) Uani 1 1 d . . .
O4 O 1.21755(15) 0.83777(13) 0.18650(13) 0.0350(3) Uani 1 1 d . . .
O5 O 0.71385(15) 0.16819(15) -0.01316(13) 0.0382(3) Uani 1 1 d . . .
O1 O 0.83342(15) 0.40623(14) 0.12447(13) 0.0358(3) Uani 1 1 d . . .
O3 O 0.79074(15) 0.62593(15) 0.04440(15) 0.0401(4) Uani 1 1 d . . .
C19 C 1.34558(19) 0.68538(19) 0.27453(17) 0.0290(4) Uani 1 1 d . . .
C7 C 0.9558(2) 0.23078(19) 0.17321(18) 0.0297(4) Uani 1 1 d . . .
C13 C 1.1300(2) 0.77185(19) 0.34436(18) 0.0311(4) Uani 1 1 d . . .
C24 C 1.3463(2) 0.5618(2) 0.2630(2) 0.0387(5) Uani 1 1 d . . .
H24 H 1.2628 0.4972 0.2247 0.046 Uiso 1 1 calc R . .
C1 C 0.71004(19) 0.25527(19) 0.21309(18) 0.0306(4) Uani 1 1 d . . .
C8 C 1.0709(2) 0.3242(2) 0.2644(2) 0.0396(5) Uani 1 1 d . . .
H8 H 1.0691 0.4112 0.2933 0.048 Uiso 1 1 calc R . .
C11 C 1.0782(3) 0.0724(2) 0.1796(2) 0.0476(6) Uani 1 1 d . . .
H11 H 1.0807 -0.0144 0.1505 0.057 Uiso 1 1 calc R . .
C12 C 0.9611(2) 0.1049(2) 0.1308(2) 0.0388(5) Uani 1 1 d . . .
H12 H 0.8833 0.0404 0.0675 0.047 Uiso 1 1 calc R . .
C18 C 1.0295(2) 0.6891(2) 0.35364(19) 0.0372(5) Uani 1 1 d . . .
H18 H 0.9878 0.6056 0.2904 0.045 Uiso 1 1 calc R . .
C2 C 0.7477(2) 0.3483(2) 0.3320(2) 0.0389(5) Uani 1 1 d . . .
H2 H 0.8191 0.4229 0.3597 0.047 Uiso 1 1 calc R . .
C10 C 1.1916(2) 0.1653(3) 0.2705(2) 0.0477(6) Uani 1 1 d . . .
H10 H 1.2723 0.1427 0.3040 0.057 Uiso 1 1 calc R . .
C3 C 0.6826(3) 0.3337(3) 0.4105(2) 0.0466(6) Uani 1 1 d . . .
H3 H 0.7099 0.3977 0.4922 0.056 Uiso 1 1 calc R . .
C22 C 1.5872(2) 0.6235(3) 0.3609(2) 0.0507(6) Uani 1 1 d . . .
H22 H 1.6700 0.6020 0.3898 0.061 Uiso 1 1 calc R . .
C20 C 1.4690(2) 0.7786(2) 0.3308(2) 0.0422(5) Uani 1 1 d . . .
H20 H 1.4709 0.8641 0.3396 0.051 Uiso 1 1 calc R . .
C6 C 0.6061(2) 0.1479(2) 0.1748(2) 0.0437(5) Uani 1 1 d . . .
H6 H 0.5793 0.0827 0.0938 0.052 Uiso 1 1 calc R . .
C23 C 1.4664(3) 0.5310(3) 0.3063(2) 0.0495(6) Uani 1 1 d . . .
H23 H 1.4653 0.4459 0.2983 0.059 Uiso 1 1 calc R . .
C21 C 1.5894(2) 0.7466(3) 0.3742(2) 0.0511(6) Uani 1 1 d . . .
H21 H 1.6736 0.8104 0.4133 0.061 Uiso 1 1 calc R . .
C16 C 1.0489(3) 0.8483(3) 0.5469(2) 0.0494(6) Uani 1 1 d . . .
H16 H 1.0213 0.8747 0.6163 0.059 Uiso 1 1 calc R . .
C9 C 1.1881(2) 0.2911(3) 0.3132(2) 0.0481(6) Uani 1 1 d . . .
H9 H 1.2664 0.3552 0.3762 0.058 Uiso 1 1 calc R . .
C25 C 0.8239(3) 0.7498(3) 0.0454(4) 0.0624(8) Uani 1 1 d . . .
H25A H 0.8460 0.7459 -0.0288 0.075 Uiso 1 1 calc R . .
H25B H 0.9040 0.8054 0.1213 0.075 Uiso 1 1 calc R . .
C14 C 1.1886(3) 0.8927(2) 0.4373(2) 0.0503(6) Uani 1 1 d . . .
H14 H 1.2571 0.9505 0.4319 0.060 Uiso 1 1 calc R . .
C15 C 1.1483(3) 0.9304(3) 0.5383(3) 0.0616(8) Uani 1 1 d . . .
H15 H 1.1898 1.0136 0.6022 0.074 Uiso 1 1 calc R . .
C17 C 0.9899(2) 0.7287(3) 0.4556(2) 0.0457(5) Uani 1 1 d . . .
H17 H 0.9211 0.6719 0.4618 0.055 Uiso 1 1 calc R . .
C5 C 0.5404(3) 0.1345(3) 0.2539(3) 0.0559(7) Uani 1 1 d . . .
H5 H 0.4685 0.0605 0.2270 0.067 Uiso 1 1 calc R . .
C4 C 0.5792(3) 0.2277(3) 0.3708(2) 0.0501(6) Uani 1 1 d . . .
H4 H 0.5337 0.2184 0.4247 0.060 Uiso 1 1 calc R . .
C27 C 0.6020(4) 0.7048(4) 0.0434(4) 0.0807(11) Uani 1 1 d . . .
H27A H 0.5247 0.6683 -0.0379 0.097 Uiso 1 1 calc R . .
H27B H 0.5680 0.7426 0.1105 0.097 Uiso 1 1 calc R . .
C28 C 0.6678(3) 0.6057(4) 0.0646(4) 0.0819(12) Uani 1 1 d . . .
H28A H 0.6859 0.6120 0.1511 0.098 Uiso 1 1 calc R . .
H28B H 0.6079 0.5197 0.0061 0.098 Uiso 1 1 calc R . .
C26 C 0.7071(4) 0.8006(4) 0.0440(6) 0.1132(18) Uani 1 1 d . . .
H26A H 0.6736 0.8197 -0.0313 0.136 Uiso 1 1 calc R . .
H26B H 0.7325 0.8805 0.1187 0.136 Uiso 1 1 calc R . .
H5A H 0.747(5) 0.167(4) -0.095(4) 0.130(16) Uiso 1 1 d . . .
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'
Li Li -0.0003 0.0001 '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
O2 P1 O4 118.25(8) . . ?
O2 P1 C13 110.18(9) . . ?
O4 P1 C13 106.12(9) . . ?
O2 P1 C19 107.70(8) . . ?
O4 P1 C19 107.47(9) . . ?
C13 P1 C19 106.53(9) . . ?
O1 P2 O5 117.71(8) . . ?
O1 P2 C1 111.70(9) . . ?
O5 P2 C1 104.07(9) . . ?
O1 P2 C7 109.64(9) . . ?
O5 P2 C7 107.85(9) . . ?
C1 P2 C7 105.01(9) . . ?
O1 Li1 O2 121.56(17) . . ?
O1 Li1 O3 104.24(16) . . ?
O2 Li1 O3 106.36(17) . . ?
O1 Li1 O2 113.21(17) . 2_765 ?
O2 Li1 O2 93.54(15) . 2_765 ?
O3 Li1 O2 118.54(17) . 2_765 ?
O1 Li1 Li1 132.0(2) . 2_765 ?
O2 Li1 Li1 47.32(11) . 2_765 ?
O3 Li1 Li1 123.8(2) . 2_765 ?
O2 Li1 Li1 46.22(11) 2_765 2_765 ?
P1 O2 Li1 142.57(13) . . ?
P1 O2 Li1 129.42(13) . 2_765 ?
Li1 O2 Li1 86.46(15) . 2_765 ?
P2 O1 Li1 140.58(14) . . ?
C25 O3 C28 109.1(2) . . ?
C25 O3 Li1 129.56(17) . . ?
C28 O3 Li1 120.55(18) . . ?
C24 C19 C20 118.61(19) . . ?
C24 C19 P1 119.86(15) . . ?
C20 C19 P1 121.53(16) . . ?
C12 C7 C8 119.04(19) . . ?
C12 C7 P2 120.83(16) . . ?
C8 C7 P2 120.11(15) . . ?
C14 C13 C18 118.90(19) . . ?
C14 C13 P1 120.09(16) . . ?
C18 C13 P1 120.99(16) . . ?
C23 C24 C19 121.0(2) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 P2 121.43(16) . . ?
C2 C1 P2 119.84(16) . . ?
C9 C8 C7 120.2(2) . . ?
C12 C11 C10 120.1(2) . . ?
C11 C12 C7 120.6(2) . . ?
C13 C18 C17 119.9(2) . . ?
C3 C2 C1 120.7(2) . . ?
C9 C10 C11 120.1(2) . . ?
C4 C3 C2 120.0(2) . . ?
C21 C22 C23 120.5(2) . . ?
C19 C20 C21 119.9(2) . . ?
C1 C6 C5 120.3(2) . . ?
C22 C23 C24 119.8(2) . . ?
C22 C21 C20 120.2(2) . . ?
C17 C16 C15 119.8(2) . . ?
C10 C9 C8 120.1(2) . . ?
O3 C25 C26 107.7(2) . . ?
C13 C14 C15 120.5(2) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C17 C18 120.6(2) . . ?
C4 C5 C6 120.0(2) . . ?
C3 C4 C5 120.4(2) . . ?
C26 C27 C28 105.5(3) . . ?
O3 C28 C27 107.5(2) . . ?
C25 C26 C27 107.8(3) . . ?
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 O2 1.4968(14) . ?
P1 O4 1.5086(14) . ?
P1 C13 1.794(2) . ?
P1 C19 1.799(2) . ?
P2 O1 1.4815(14) . ?
P2 O5 1.5311(15) . ?
P2 C1 1.790(2) . ?
P2 C7 1.796(2) . ?
Li1 O1 1.896(4) . ?
Li1 O2 1.938(4) . ?
Li1 O3 1.954(4) . ?
Li1 O2 1.973(3) 2_765 ?
Li1 Li1 2.679(6) 2_765 ?
O2 Li1 1.973(3) 2_765 ?
O3 C25 1.414(3) . ?
O3 C28 1.410(3) . ?
C19 C24 1.383(3) . ?
C19 C20 1.391(3) . ?
C7 C12 1.384(3) . ?
C7 C8 1.388(3) . ?
C13 C14 1.379(3) . ?
C13 C18 1.388(3) . ?
C24 C23 1.378(3) . ?
C1 C6 1.378(3) . ?
C1 C2 1.385(3) . ?
C8 C9 1.382(3) . ?
C11 C12 1.377(3) . ?
C11 C10 1.375(4) . ?
C18 C17 1.389(3) . ?
C2 C3 1.378(3) . ?
C10 C9 1.378(4) . ?
C3 C4 1.362(4) . ?
C22 C21 1.367(4) . ?
C22 C23 1.368(4) . ?
C20 C21 1.390(3) . ?
C6 C5 1.386(3) . ?
C16 C17 1.362(4) . ?
C16 C15 1.371(4) . ?
C25 C26 1.450(4) . ?
C14 C15 1.382(3) . ?
C5 C4 1.367(4) . ?
C27 C26 1.454(5) . ?
C27 C28 1.474(4) . ?
