#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:57:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178797 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/51/4105177.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_4105177
loop_
_publ_author_name
'Leah N. Appelhans'
'Monica Kosa'
'A. V. Radha'
'Petra Simoncic'
'Alexandra Navrotsky'
'Michele Parrinello'
'Anthony K. Cheetham'
_publ_contact_author_address
;
Department of Materials Science and Metallurgy
University of Cambridge
Cambridge CB2 3QZ, UK
;
_publ_contact_author_email       akc30@cam.ac.uk
_publ_contact_author_name        'Anthony K. Cheetham'
_publ_contact_author_phone       '+44 01223-767061'
_publ_section_title
;
 Phase Selection and Energetics in Chiral Alkaline Earth Tartrates and
 Their Racemic and Meso Analogues: Synthetic, Structural, Computational,
 and Calorimetric Studies
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15375
_journal_page_last               15386
_journal_paper_doi               10.1021/ja905690t
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C4 H12 Ca O10'
_chemical_formula_weight         260.22
_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                94.887(6)
_cell_angle_beta                 105.914(6)
_cell_angle_gamma                107.662(5)
_cell_formula_units_Z            2
_cell_length_a                   6.2584(15)
_cell_length_b                   8.251(2)
_cell_length_c                   10.448(3)
_cell_measurement_temperature    298(2)
_cell_volume                     486.0(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      298(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_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  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0895
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3923
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0517
_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)+(0.0585P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                1344
_reflns_number_total             1902
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja905690t_si_002_04.cif
_cod_data_source_block           cadltm
_cod_database_code               4105177
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
Ca1 Ca 0.34098(13) 0.69009(9) 0.27353(7) 0.0224(3) Uani 1 1 d .
C1 C 0.3833(6) 0.3490(4) 0.1130(3) 0.0213(8) Uani 1 1 d .
C2 C 0.5815(6) 0.3666(4) 0.2430(4) 0.0208(8) Uani 1 1 d .
H1 H 0.530(6) 0.277(5) 0.285(4) 0.025 Uiso 1 1 d .
C3 C 0.8058(6) 0.3700(4) 0.2076(4) 0.0214(8) Uani 1 1 d .
H2 H 0.770(6) 0.276(5) 0.140(4) 0.026 Uiso 1 1 d .
C4 C 0.9842(6) 0.3502(4) 0.3349(3) 0.0208(8) Uani 1 1 d .
O1 O 0.3172(4) 0.4771(3) 0.0923(2) 0.0290(6) Uani 1 1 d .
O2 O 0.2964(4) 0.2036(3) 0.0347(2) 0.0295(6) Uani 1 1 d .
O3 O 0.6216(5) 0.5214(3) 0.3328(3) 0.0274(6) Uani 1 1 d .
H3 H 0.669(7) 0.513(5) 0.418(4) 0.033 Uiso 1 1 d .
O4 O 0.9110(4) 0.5269(3) 0.1671(2) 0.0253(6) Uani 1 1 d D
H4 H 0.849(6) 0.524(5) 0.081(2) 0.030 Uiso 1 1 d D
O5 O 0.9258(5) 0.2073(3) 0.3731(3) 0.0315(7) Uani 1 1 d .
O6 O 1.1726(4) 0.4732(3) 0.3925(3) 0.0310(7) Uani 1 1 d .
O7 O 0.6022(5) 0.8127(3) 0.5026(3) 0.0347(7) Uani 1 1 d D
H5 H 0.711(6) 0.774(5) 0.529(4) 0.052 Uiso 1 1 d D
H6 H 0.676(7) 0.916(3) 0.537(4) 0.052 Uiso 1 1 d D
O8 O 0.6903(5) 0.8757(3) 0.2288(3) 0.0337(7) Uani 1 1 d D
H7 H 0.763(7) 0.977(3) 0.263(4) 0.050 Uiso 1 1 d D
H8 H 0.688(8) 0.866(6) 0.149(2) 0.050 Uiso 1 1 d D
O9 O 0.1893(5) 0.8525(4) 0.1023(3) 0.0379(7) Uani 1 1 d D
H9 H 0.049(4) 0.828(6) 0.057(4) 0.057 Uiso 1 1 d D
H10 H 0.251(8) 0.949(3) 0.087(5) 0.057 Uiso 1 1 d D
O10 O 0.1414(5) 0.8454(3) 0.3835(3) 0.0305(6) Uani 1 1 d D
H11 H 0.004(4) 0.827(5) 0.337(4) 0.046 Uiso 1 1 d D
H12 H 0.116(8) 0.805(5) 0.450(3) 0.046 Uiso 1 1 d 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 '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
O6 Ca1 O1 92.90(9) 1_455 .
O6 Ca1 O7 79.68(10) 1_455 .
O1 Ca1 O7 135.54(9) . .
O6 Ca1 O8 149.08(9) 1_455 .
O1 Ca1 O8 86.16(9) . .
O7 Ca1 O8 79.53(10) . .
O6 Ca1 O10 80.47(9) 1_455 .
O1 Ca1 O10 148.93(9) . .
O7 Ca1 O10 73.43(9) . .
O8 Ca1 O10 114.80(10) . .
O6 Ca1 O9 136.24(10) 1_455 .
O1 Ca1 O9 88.95(10) . .
O7 Ca1 O9 126.20(10) . .
O8 Ca1 O9 74.68(10) . .
O10 Ca1 O9 75.97(10) . .
O6 Ca1 O4 64.96(8) 1_455 1_455
O1 Ca1 O4 75.03(9) . 1_455
O7 Ca1 O4 135.44(10) . 1_455
O8 Ca1 O4 143.02(9) . 1_455
O10 Ca1 O4 74.68(9) . 1_455
O9 Ca1 O4 73.44(9) . 1_455
O6 Ca1 O3 73.48(9) 1_455 .
O1 Ca1 O3 63.90(8) . .
O7 Ca1 O3 72.02(8) . .
O8 Ca1 O3 78.46(10) . .
O10 Ca1 O3 139.66(9) . .
O9 Ca1 O3 142.86(10) . .
O4 Ca1 O3 118.65(9) 1_455 .
O1 C1 O2 125.1(3) . .
O1 C1 C2 118.7(3) . .
O2 C1 C2 116.2(3) . .
O3 C2 C1 108.8(3) . .
O3 C2 C3 111.4(3) . .
C1 C2 C3 109.2(3) . .
O3 C2 H1 106(2) . .
C1 C2 H1 108(2) . .
C3 C2 H1 113(2) . .
O4 C3 C2 112.4(3) . .
O4 C3 C4 108.9(3) . .
C2 C3 C4 107.8(3) . .
O4 C3 H2 110(2) . .
C2 C3 H2 110(2) . .
C4 C3 H2 108(2) . .
O6 C4 O5 124.7(3) . .
O6 C4 C3 119.4(3) . .
O5 C4 C3 115.9(3) . .
C1 O1 Ca1 122.7(2) . .
C2 O3 Ca1 119.41(19) . .
C2 O3 H3 113(2) . .
Ca1 O3 H3 116(2) . .
C3 O4 Ca1 119.77(19) . 1_655
C3 O4 H4 112(3) . .
Ca1 O4 H4 118(3) 1_655 .
C4 O6 Ca1 121.8(2) . 1_655
Ca1 O7 H5 116(3) . .
Ca1 O7 H6 128(3) . .
H5 O7 H6 99(4) . .
Ca1 O8 H7 126(3) . .
Ca1 O8 H8 116(3) . .
H7 O8 H8 106(5) . .
Ca1 O9 H9 125(3) . .
Ca1 O9 H10 131(3) . .
H9 O9 H10 103(4) . .
Ca1 O10 H11 113(3) . .
Ca1 O10 H12 112(3) . .
H11 O10 H12 99(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ca1 O6 2.411(3) 1_455
Ca1 O1 2.411(3) .
Ca1 O7 2.421(3) .
Ca1 O8 2.448(3) .
Ca1 O10 2.456(3) .
Ca1 O9 2.479(3) .
Ca1 O4 2.489(3) 1_455
Ca1 O3 2.537(2) .
C1 O1 1.261(4) .
C1 O2 1.264(4) .
C1 C2 1.529(5) .
C2 O3 1.431(4) .
C2 C3 1.540(5) .
C2 H1 0.91(4) .
C3 O4 1.421(4) .
C3 C4 1.542(4) .
C3 H2 0.93(4) .
C4 O6 1.250(4) .
C4 O5 1.257(4) .
O3 H3 0.88(4) .
O4 Ca1 2.489(3) 1_655
O4 H4 0.868(18) .
O6 Ca1 2.411(3) 1_655
O7 H5 0.83(2) .
O7 H6 0.83(2) .
O8 H7 0.81(2) .
O8 H8 0.83(2) .
O9 H9 0.83(2) .
O9 H10 0.82(2) .
O10 H11 0.82(2) .
O10 H12 0.83(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O6 0.88(4) 1.93(4) 2.795(4) 169(4) 2_766
O4 H4 O1 0.868(18) 1.83(2) 2.687(3) 171(4) 2_665
O7 H5 O5 0.83(2) 2.17(3) 2.944(4) 155(4) 2_766
O7 H6 O10 0.83(2) 1.92(2) 2.754(4) 178(5) 2_676
O8 H7 O5 0.81(2) 1.94(2) 2.750(4) 170(4) 1_565
O8 H8 O2 0.83(2) 1.99(2) 2.805(4) 167(4) 2_665
O9 H9 O2 0.83(2) 2.03(2) 2.855(4) 172(5) 2_565
O9 H10 O2 0.82(2) 2.17(2) 2.961(4) 161(4) 1_565
O10 H11 O8 0.82(2) 2.15(2) 2.939(4) 160(4) 1_455
O10 H12 O5 0.83(2) 1.94(2) 2.739(4) 161(4) 2_666
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_4
O1 C1 C2 O3 12.3(4) . .
O2 C1 C2 O3 -166.9(3) . .
O1 C1 C2 C3 -109.4(3) . .
O2 C1 C2 C3 71.3(4) . .
O3 C2 C3 O4 -48.8(4) . .
C1 C2 C3 O4 71.4(4) . .
O3 C2 C3 C4 71.1(3) . .
C1 C2 C3 C4 -168.7(3) . .
O4 C3 C4 O6 8.2(4) . .
C2 C3 C4 O6 -114.0(4) . .
O4 C3 C4 O5 -171.9(3) . .
C2 C3 C4 O5 66.0(4) . .
O2 C1 O1 Ca1 149.9(3) . .
C2 C1 O1 Ca1 -29.3(4) . .
O6 Ca1 O1 C1 -46.4(3) 1_455 .
O7 Ca1 O1 C1 31.8(3) . .
O8 Ca1 O1 C1 102.6(3) . .
O10 Ca1 O1 C1 -122.7(3) . .
O9 Ca1 O1 C1 177.3(3) . .
O4 Ca1 O1 C1 -109.5(3) 1_455 .
O3 Ca1 O1 C1 23.6(3) . .
C1 C2 O3 Ca1 8.0(4) . .
C3 C2 O3 Ca1 128.4(2) . .
O6 Ca1 O3 C2 86.7(3) 1_455 .
O1 Ca1 O3 C2 -15.1(2) . .
O7 Ca1 O3 C2 171.0(3) . .
O8 Ca1 O3 C2 -106.4(3) . .
O10 Ca1 O3 C2 138.7(2) . .
O9 Ca1 O3 C2 -62.2(3) . .
O4 Ca1 O3 C2 38.4(3) 1_455 .
C2 C3 O4 Ca1 129.8(2) . 1_655
C4 C3 O4 Ca1 10.5(4) . 1_655
O5 C4 O6 Ca1 155.7(3) . 1_655
C3 C4 O6 Ca1 -24.3(4) . 1_655
