#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:57:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178797 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/51/4105176.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_4105176
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 H4 Ca O6'
_chemical_formula_weight         188.15
_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                 121.066(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.593(6)
_cell_length_b                   7.906(3)
_cell_length_c                   9.462(3)
_cell_measurement_temperature    298(2)
_cell_volume                     1127.3(7)
_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 0.960
_diffrn_measured_fraction_theta_max 0.960
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4611
_diffrn_reflns_theta_full        26.66
_diffrn_reflns_theta_max         26.66
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    1.088
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick 2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.217
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1144
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0344
_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)+(0.0394P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                995
_reflns_number_total             1144
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja905690t_si_002_03.cif
_cod_data_source_block           150mcam
_cod_database_code               4105176
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
Ca1 Ca 0.37471(3) 0.23081(6) 0.70140(6) 0.01618(18) Uani 1 1 d .
O1 O 0.53228(11) 0.2322(2) 0.9175(2) 0.0201(4) Uani 1 1 d .
O2 O 0.45259(12) 0.3343(2) 1.0161(2) 0.0225(4) Uani 1 1 d .
O3 O 0.60376(13) 0.4604(2) 1.2945(2) 0.0200(4) Uani 1 1 d D
H3 H 0.582(2) 0.412(4) 1.337(4) 0.024 Uiso 1 1 d D
O4 O 0.61308(13) 0.0806(2) 1.3134(2) 0.0233(4) Uani 1 1 d D
H4 H 0.626(2) 0.101(4) 1.405(4) 0.028 Uiso 1 1 d D
O5 O 0.67173(13) -0.0658(2) 1.1457(2) 0.0240(4) Uani 1 1 d .
O6 O 0.72575(11) 0.1685(2) 1.1001(2) 0.0204(4) Uani 1 1 d .
C1 C 0.52595(16) 0.3027(3) 1.0307(3) 0.0175(5) Uani 1 1 d .
C2 C 0.61348(17) 0.3501(3) 1.1863(3) 0.0168(5) Uani 1 1 d D
H1 H 0.6491(17) 0.413(3) 1.151(3) 0.020 Uiso 1 1 d D
C3 C 0.66410(17) 0.1877(3) 1.2731(3) 0.0180(5) Uani 1 1 d D
H2 H 0.7189(14) 0.222(4) 1.370(3) 0.022 Uiso 1 1 d D
C4 C 0.68904(15) 0.0885(3) 1.1643(3) 0.0164(5) Uani 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'
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
O5 Ca1 O6 77.27(7) 5_657 8_455
O5 Ca1 O1 144.21(6) 5_657 2_656
O6 Ca1 O1 132.12(7) 8_455 2_656
O5 Ca1 O1 95.19(7) 5_657 .
O6 Ca1 O1 149.08(6) 8_455 .
O1 Ca1 O1 69.05(8) 2_656 .
O5 Ca1 O3 129.03(7) 5_657 5_667
O6 Ca1 O3 78.83(6) 8_455 5_667
O1 Ca1 O3 82.39(6) 2_656 5_667
O1 Ca1 O3 83.36(6) . 5_667
O5 Ca1 O4 63.78(6) 5_657 5_657
O6 Ca1 O4 114.38(7) 8_455 5_657
O1 Ca1 O4 83.04(6) 2_656 5_657
O1 Ca1 O4 87.58(6) . 5_657
O3 Ca1 O4 164.86(7) 5_667 5_657
O5 Ca1 O6 108.75(7) 5_657 2_656
O6 Ca1 O6 68.30(7) 8_455 2_656
O1 Ca1 O6 73.78(6) 2_656 2_656
O1 Ca1 O6 141.10(6) . 2_656
O3 Ca1 O6 102.97(6) 5_667 2_656
O4 Ca1 O6 76.80(6) 5_657 2_656
O5 Ca1 O2 68.41(7) 5_657 .
O6 Ca1 O2 99.67(6) 8_455 .
O1 Ca1 O2 115.74(6) 2_656 .
O1 Ca1 O2 50.47(6) . .
O3 Ca1 O2 72.22(6) 5_667 .
O4 Ca1 O2 110.83(6) 5_657 .
O6 Ca1 O2 167.89(6) 2_656 .
O5 Ca1 C1 82.42(7) 5_657 .
O6 Ca1 C1 124.28(7) 8_455 .
O1 Ca1 C1 91.87(7) 2_656 .
O1 Ca1 C1 25.26(6) . .
O3 Ca1 C1 75.11(7) 5_667 .
O4 Ca1 C1 101.27(7) 5_657 .
O6 Ca1 C1 165.64(7) 2_656 .
O2 Ca1 C1 25.29(6) . .
O5 Ca1 C4 114.84(7) 5_657 2_656
O6 Ca1 C4 89.08(6) 8_455 2_656
O1 Ca1 C4 56.55(6) 2_656 2_656
O1 Ca1 C4 120.75(6) . 2_656
O3 Ca1 C4 109.04(6) 5_667 2_656
O4 Ca1 C4 65.63(6) 5_657 2_656
O6 Ca1 C4 20.79(6) 2_656 2_656
O2 Ca1 C4 171.20(6) . 2_656
C1 Ca1 C4 145.96(7) . 2_656
O5 Ca1 Ca1 122.76(5) 5_657 2_656
O6 Ca1 Ca1 158.48(5) 8_455 2_656
O1 Ca1 Ca1 34.82(4) 2_656 2_656
O1 Ca1 Ca1 34.24(4) . 2_656
O3 Ca1 Ca1 81.65(5) 5_667 2_656
O4 Ca1 Ca1 84.03(5) 5_657 2_656
O6 Ca1 Ca1 107.85(4) 2_656 2_656
O2 Ca1 Ca1 82.77(4) . 2_656
C1 Ca1 Ca1 57.85(5) . 2_656
C4 Ca1 Ca1 88.78(4) 2_656 2_656
O5 Ca1 Ca1 93.87(6) 5_657 7_556
O6 Ca1 Ca1 34.91(4) 8_455 7_556
O1 Ca1 Ca1 103.02(6) 2_656 7_556
O1 Ca1 Ca1 170.93(5) . 7_556
O3 Ca1 Ca1 91.35(5) 5_667 7_556
O4 Ca1 Ca1 95.96(5) 5_657 7_556
O6 Ca1 Ca1 33.39(4) 2_656 7_556
O2 Ca1 Ca1 134.57(4) . 7_556
C1 Ca1 Ca1 158.47(5) . 7_556
C4 Ca1 Ca1 54.18(5) 2_656 7_556
Ca1 Ca1 Ca1 137.71(3) 2_656 7_556
C1 O1 Ca1 140.71(16) . 2_656
C1 O1 Ca1 98.77(15) . .
Ca1 O1 Ca1 110.95(7) 2_656 .
C1 O2 Ca1 88.21(15) . .
C2 O3 Ca1 122.95(14) . 5_667
C2 O3 H3 110(2) . .
Ca1 O3 H3 126(2) 5_667 .
C3 O4 Ca1 119.37(15) . 5_657
C3 O4 H4 108(2) . .
Ca1 O4 H4 106(2) 5_657 .
C4 O5 Ca1 125.79(16) . 5_657
C4 O6 Ca1 134.03(16) . 8_556
C4 O6 Ca1 114.23(15) . 2_656
Ca1 O6 Ca1 111.70(7) 8_556 2_656
O2 C1 O1 122.2(2) . .
O2 C1 C2 121.8(2) . .
O1 C1 C2 116.1(2) . .
O2 C1 Ca1 66.50(14) . .
O1 C1 Ca1 55.97(13) . .
C2 C1 Ca1 169.61(16) . .
O3 C2 C1 114.1(2) . .
O3 C2 C3 112.3(2) . .
C1 C2 C3 109.1(2) . .
O3 C2 H1 105.5(17) . .
C1 C2 H1 107.4(17) . .
C3 C2 H1 108.1(17) . .
O4 C3 C4 108.4(2) . .
O4 C3 C2 111.6(2) . .
C4 C3 C2 111.0(2) . .
O4 C3 H2 111.9(18) . .
C4 C3 H2 106.9(18) . .
C2 C3 H2 106.9(18) . .
O5 C4 O6 124.8(2) . .
O5 C4 C3 117.6(2) . .
O6 C4 C3 117.6(2) . .
O5 C4 Ca1 105.33(16) . 2_656
O6 C4 Ca1 44.97(12) . 2_656
C3 C4 Ca1 118.69(15) . 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ca1 O5 2.3835(19) 5_657
Ca1 O6 2.4142(19) 8_455
Ca1 O1 2.4172(19) 2_656
Ca1 O1 2.4528(19) .
Ca1 O3 2.468(2) 5_667
Ca1 O4 2.482(2) 5_657
Ca1 O6 2.510(2) 2_656
Ca1 O2 2.684(2) .
Ca1 C1 2.925(3) .
Ca1 C4 3.239(3) 2_656
Ca1 Ca1 4.0122(18) 2_656
Ca1 Ca1 4.0758(15) 7_556
O1 C1 1.263(3) .
O1 Ca1 2.4172(19) 2_656
O2 C1 1.250(3) .
O3 C2 1.420(3) .
O3 Ca1 2.468(2) 5_667
O3 H3 0.79(3) .
O4 C3 1.422(3) .
O4 Ca1 2.482(2) 5_657
O4 H4 0.79(3) .
O5 C4 1.248(3) .
O5 Ca1 2.3835(19) 5_657
O6 C4 1.261(3) .
O6 Ca1 2.4142(19) 8_556
O6 Ca1 2.510(2) 2_656
C1 C2 1.530(3) .
C2 C3 1.537(3) .
C2 H1 0.985(17) .
C3 C4 1.528(3) .
C3 H2 0.966(18) .
C4 Ca1 3.239(3) 2_656
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 O2 0.79(3) 1.88(3) 2.650(3) 165(3) 2_657
O4 H4 O5 0.79(3) 2.00(3) 2.759(3) 160(3) 6_556
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
O5 Ca1 O1 C1 -59.82(15) 5_657 .
O6 Ca1 O1 C1 14.0(2) 8_455 .
O1 Ca1 O1 C1 153.31(13) 2_656 .
O3 Ca1 O1 C1 68.94(15) 5_667 .
O4 Ca1 O1 C1 -123.22(15) 5_657 .
O6 Ca1 O1 C1 171.38(14) 2_656 .
O2 Ca1 O1 C1 -3.46(13) . .
C4 Ca1 O1 C1 177.16(14) 2_656 .
Ca1 Ca1 O1 C1 153.85(18) 2_656 .
Ca1 Ca1 O1 C1 123.5(3) 7_556 .
O5 Ca1 O1 Ca1 146.33(7) 5_657 2_656
O6 Ca1 O1 Ca1 -139.88(10) 8_455 2_656
O1 Ca1 O1 Ca1 -0.54(9) 2_656 2_656
O3 Ca1 O1 Ca1 -84.91(8) 5_667 2_656
O4 Ca1 O1 Ca1 82.94(8) 5_657 2_656
O6 Ca1 O1 Ca1 17.54(14) 2_656 2_656
O2 Ca1 O1 Ca1 -157.31(11) . 2_656
C1 Ca1 O1 Ca1 -153.85(18) . 2_656
C4 Ca1 O1 Ca1 23.32(10) 2_656 2_656
Ca1 Ca1 O1 Ca1 -30.3(4) 7_556 2_656
O5 Ca1 O2 C1 120.37(15) 5_657 .
O6 Ca1 O2 C1 -167.56(14) 8_455 .
O1 Ca1 O2 C1 -20.68(16) 2_656 .
O1 Ca1 O2 C1 3.46(13) . .
O3 Ca1 O2 C1 -92.69(15) 5_667 .
O4 Ca1 O2 C1 71.58(15) 5_657 .
O6 Ca1 O2 C1 -160.9(3) 2_656 .
C4 Ca1 O2 C1 7.0(5) 2_656 .
Ca1 Ca1 O2 C1 -9.18(14) 2_656 .
Ca1 Ca1 O2 C1 -166.36(12) 7_556 .
Ca1 O2 C1 O1 -6.1(2) . .
Ca1 O2 C1 C2 172.9(2) . .
Ca1 O1 C1 O2 146.2(2) 2_656 .
Ca1 O1 C1 O2 6.8(3) . .
Ca1 O1 C1 C2 -32.8(4) 2_656 .
Ca1 O1 C1 C2 -172.30(17) . .
Ca1 O1 C1 Ca1 139.4(3) 2_656 .
O5 Ca1 C1 O2 -54.03(14) 5_657 .
O6 Ca1 C1 O2 14.89(17) 8_455 .
O1 Ca1 C1 O2 161.44(14) 2_656 .
O1 Ca1 C1 O2 -173.7(2) . .
O3 Ca1 C1 O2 79.82(14) 5_667 .
O4 Ca1 C1 O2 -115.28(14) 5_657 .
O6 Ca1 C1 O2 164.0(2) 2_656 .
C4 Ca1 C1 O2 -178.10(13) 2_656 .
Ca1 Ca1 C1 O2 169.22(16) 2_656 .
Ca1 Ca1 C1 O2 27.2(2) 7_556 .
O5 Ca1 C1 O1 119.71(15) 5_657 .
O6 Ca1 C1 O1 -171.37(13) 8_455 .
O1 Ca1 C1 O1 -24.82(12) 2_656 .
O3 Ca1 C1 O1 -106.44(15) 5_667 .
O4 Ca1 C1 O1 58.46(15) 5_657 .
O6 Ca1 C1 O1 -22.3(3) 2_656 .
O2 Ca1 C1 O1 173.7(2) . .
C4 Ca1 C1 O1 -4.4(2) 2_656 .
Ca1 Ca1 C1 O1 -17.03(12) 2_656 .
Ca1 Ca1 C1 O1 -159.01(13) 7_556 .
O5 Ca1 C1 C2 161.6(9) 5_657 .
O6 Ca1 C1 C2 -129.5(9) 8_455 .
O1 Ca1 C1 C2 17.1(9) 2_656 .
O1 Ca1 C1 C2 41.9(9) . .
O3 Ca1 C1 C2 -64.5(9) 5_667 .
O4 Ca1 C1 C2 100.4(9) 5_657 .
O6 Ca1 C1 C2 19.6(11) 2_656 .
O2 Ca1 C1 C2 -144.4(10) . .
C4 Ca1 C1 C2 37.5(10) 2_656 .
Ca1 Ca1 C1 C2 24.9(9) 2_656 .
Ca1 Ca1 C1 C2 -117.1(9) 7_556 .
Ca1 O3 C2 C1 -97.9(2) 5_667 .
Ca1 O3 C2 C3 137.22(17) 5_667 .
O2 C1 C2 O3 -12.0(3) . .
O1 C1 C2 O3 167.1(2) . .
Ca1 C1 C2 O3 129.1(9) . .
O2 C1 C2 C3 114.6(3) . .
O1 C1 C2 C3 -66.4(3) . .
Ca1 C1 C2 C3 -104.4(9) . .
Ca1 O4 C3 C4 22.2(2) 5_657 .
Ca1 O4 C3 C2 144.71(16) 5_657 .
O3 C2 C3 O4 69.9(3) . .
C1 C2 C3 O4 -57.7(3) . .
O3 C2 C3 C4 -169.0(2) . .
C1 C2 C3 C4 63.4(3) . .
Ca1 O5 C4 O6 169.03(17) 5_657 .
Ca1 O5 C4 C3 -10.8(3) 5_657 .
Ca1 O5 C4 Ca1 -145.62(12) 5_657 2_656
Ca1 O6 C4 O5 -101.5(3) 8_556 .
Ca1 O6 C4 O5 76.1(3) 2_656 .
Ca1 O6 C4 C3 78.3(3) 8_556 .
Ca1 O6 C4 C3 -104.0(2) 2_656 .
Ca1 O6 C4 Ca1 -177.6(3) 8_556 2_656
O4 C3 C4 O5 -8.2(3) . .
C2 C3 C4 O5 -131.1(2) . .
O4 C3 C4 O6 172.0(2) . .
C2 C3 C4 O6 49.0(3) . .
O4 C3 C4 Ca1 120.57(17) . 2_656
C2 C3 C4 Ca1 -2.4(3) . 2_656
