#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:54:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178796 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/50/4105051.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_4105051
loop_
_publ_author_name
'Charles L. Perrin'
'Jonathan S. Lau'
'Yeong-Joon Kim'
'Phaneendrasai Karri'
'Curtis Moore'
'Arnold L. Rheingold'
_publ_section_title
;
 Asymmetry of the "Strongest" OHO Hydrogen Bond, in the Monoanion of
 (\+-)-α,α'-Di-tert-butylsuccinate
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13548
_journal_page_last               13554
_journal_paper_doi               10.1021/ja905806h
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C24 H54 Ca O14'
_chemical_formula_weight         606.75
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.390(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4772(6)
_cell_length_b                   14.4843(13)
_cell_length_c                   17.5838(15)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.71
_cell_volume                     1648.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω 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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13255
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_correction_T_min  0.9403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       Block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0016(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0429
_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)+(0.0221P)²+2.6120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                2716
_reflns_number_total             3021
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja905806h_si_002_5.cif
_cod_data_source_block           "'Calcium_a,a'-di-tert-butylsuccinate'"
_cod_database_code               4105051
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.7560(3) 0.32776(16) 0.60364(12) 0.0223(5) Uani 1 1 d .
C2 C 0.8959(3) 0.25125(15) 0.63560(12) 0.0206(5) Uani 1 1 d .
H2 H 1.0384 0.2775 0.6337 0.025 Uiso 1 1 calc R
C3 C 0.8718(3) 0.22757(15) 0.72120(12) 0.0207(5) Uani 1 1 d .
H3 H 0.9851 0.1824 0.7335 0.025 Uiso 1 1 calc R
C4 C 0.6748(3) 0.17639(15) 0.73921(12) 0.0209(5) Uani 1 1 d .
C5 C 0.8979(3) 0.16538(16) 0.58013(13) 0.0240(5) Uani 1 1 d .
C6 C 1.0501(4) 0.09292(17) 0.61251(15) 0.0321(6) Uani 1 1 d .
H6A H 1.0717 0.0453 0.5740 0.048 Uiso 1 1 calc R
H6B H 0.9936 0.0645 0.6577 0.048 Uiso 1 1 calc R
H6C H 1.1822 0.1227 0.6264 0.048 Uiso 1 1 calc R
C7 C 0.6865(4) 0.11943(17) 0.56567(14) 0.0301(5) Uani 1 1 d .
H7A H 0.5871 0.1654 0.5458 0.045 Uiso 1 1 calc R
H7B H 0.6386 0.0940 0.6135 0.045 Uiso 1 1 calc R
H7C H 0.6988 0.0696 0.5285 0.045 Uiso 1 1 calc R
C8 C 0.9752(4) 0.19899(18) 0.50354(15) 0.0359(6) Uani 1 1 d .
H8A H 0.9879 0.1463 0.4691 0.054 Uiso 1 1 calc R
H8B H 1.1103 0.2286 0.5116 0.054 Uiso 1 1 calc R
H8C H 0.8766 0.2436 0.4810 0.054 Uiso 1 1 calc R
C9 C 0.9120(3) 0.30965(16) 0.77966(13) 0.0234(5) Uani 1 1 d .
C10 C 0.9607(5) 0.2670(2) 0.85814(16) 0.0465(7) Uani 1 1 d .
H10A H 0.9892 0.3162 0.8953 0.070 Uiso 1 1 calc R
H10B H 1.0820 0.2269 0.8556 0.070 Uiso 1 1 calc R
H10C H 0.8421 0.2306 0.8737 0.070 Uiso 1 1 calc R
C11 C 1.0991(4) 0.3663(2) 0.75702(18) 0.0446(7) Uani 1 1 d .
H11A H 1.0670 0.3976 0.7086 0.067 Uiso 1 1 calc R
H11B H 1.2177 0.3252 0.7515 0.067 Uiso 1 1 calc R
H11C H 1.1323 0.4123 0.7965 0.067 Uiso 1 1 calc R
C12 C 0.7304(4) 0.37496(19) 0.78804(16) 0.0382(6) Uani 1 1 d .
H12A H 0.7661 0.4214 0.8269 0.057 Uiso 1 1 calc R
H12B H 0.6096 0.3399 0.8033 0.057 Uiso 1 1 calc R
H12C H 0.6985 0.4057 0.7393 0.057 Uiso 1 1 calc R
Ca1 Ca 1.0000 0.5000 0.5000 0.01911(17) Uani 1 2 d S
O1 O 0.8313(2) 0.39039(11) 0.56608(9) 0.0296(4) Uani 1 1 d .
O2 O 0.5612(2) 0.32618(11) 0.61632(9) 0.0256(4) Uani 1 1 d .
O3 O 0.6804(2) 0.10824(11) 0.78085(9) 0.0269(4) Uani 1 1 d .
O4 O 0.4967(2) 0.20693(11) 0.71229(9) 0.0247(4) Uani 1 1 d .
O1S O 1.3095(2) 0.41327(12) 0.49892(10) 0.0245(4) Uani 1 1 d .
O2S O 1.1049(3) 0.57004(13) 0.61368(10) 0.0307(4) Uani 1 1 d .
O3S O 0.5077(3) 0.53032(13) 0.63567(10) 0.0260(4) Uani 1 1 d .
H1S H 1.380(5) 0.425(2) 0.4635(19) 0.051(10) Uiso 1 1 d .
H2S H 1.380(5) 0.386(2) 0.534(2) 0.057(10) Uiso 1 1 d .
H3S H 1.216(5) 0.565(2) 0.6287(18) 0.052(10) Uiso 1 1 d .
H4S H 1.034(5) 0.584(2) 0.6523(18) 0.046(9) Uiso 1 1 d .
H5S H 0.591(6) 0.548(3) 0.664(2) 0.064(12) Uiso 1 1 d .
H6S H 0.534(5) 0.467(2) 0.6309(18) 0.052(9) Uiso 1 1 d .
H4O H 0.525(4) 0.263(2) 0.6753(16) 0.042(8) 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'
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
O1 C1 O2 121.1(2) . .
O1 C1 C2 119.30(19) . .
O2 C1 C2 119.60(19) . .
C1 C2 C3 115.74(17) . .
C1 C2 C5 111.37(17) . .
C3 C2 C5 115.25(18) . .
C1 C2 H2 104.3 . .
C3 C2 H2 104.3 . .
C5 C2 H2 104.3 . .
C4 C3 C2 115.29(17) . .
C4 C3 C9 110.30(17) . .
C2 C3 C9 116.15(18) . .
C4 C3 H3 104.5 . .
C2 C3 H3 104.5 . .
C9 C3 H3 104.5 . .
O3 C4 O4 119.48(19) . .
O3 C4 C3 120.75(19) . .
O4 C4 C3 119.73(19) . .
C6 C5 C7 108.68(19) . .
C6 C5 C8 108.3(2) . .
C7 C5 C8 108.3(2) . .
C6 C5 C2 109.33(18) . .
C7 C5 C2 114.42(18) . .
C8 C5 C2 107.64(18) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C5 C7 H7A 109.5 . .
C5 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C5 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C5 C8 H8A 109.5 . .
C5 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C5 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C12 C9 C11 108.4(2) . .
C12 C9 C10 107.1(2) . .
C11 C9 C10 108.4(2) . .
C12 C9 C3 114.98(18) . .
C11 C9 C3 110.09(19) . .
C10 C9 C3 107.65(19) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O1 Ca1 O1 180.00(6) . 3_766
O1 Ca1 O2S 90.30(7) . 3_766
O1 Ca1 O2S 89.70(6) 3_766 3_766
O1 Ca1 O2S 89.70(6) . .
O1 Ca1 O2S 90.30(7) 3_766 .
O2S Ca1 O2S 180.0 3_766 .
O1 Ca1 O1S 93.37(6) . .
O1 Ca1 O1S 86.63(6) 3_766 .
O2S Ca1 O1S 88.78(6) 3_766 .
O2S Ca1 O1S 91.22(6) . .
O1 Ca1 O1S 86.63(6) . 3_766
O1 Ca1 O1S 93.37(6) 3_766 3_766
O2S Ca1 O1S 91.22(6) 3_766 3_766
O2S Ca1 O1S 88.78(6) . 3_766
O1S Ca1 O1S 180.0 . 3_766
O1 Ca1 H1S 107.1(7) . .
O1 Ca1 H1S 72.9(7) 3_766 .
O2S Ca1 H1S 82.0(7) 3_766 .
O2S Ca1 H1S 98.0(7) . .
O1S Ca1 H1S 15.4(7) . .
O1S Ca1 H1S 164.6(7) 3_766 .
O1 Ca1 H3S 93.2(7) . .
O1 Ca1 H3S 86.8(7) 3_766 .
O2S Ca1 H3S 166.3(7) 3_766 .
O2S Ca1 H3S 13.7(7) . .
O1S Ca1 H3S 77.8(7) . .
O1S Ca1 H3S 102.2(7) 3_766 .
H1S Ca1 H3S 84.3(10) . .
C1 O1 Ca1 174.55(16) . .
C1 O2 H4O 109.3(11) . .
C4 O4 H4O 107.9(15) . .
Ca1 O1S H1S 114(2) . .
Ca1 O1S H2S 132(2) . .
H1S O1S H2S 111(3) . .
Ca1 O2S H3S 120(3) . .
Ca1 O2S H4S 130(2) . .
H3S O2S H4S 106(3) . .
H5S O3S H6S 105(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.234(3) .
C1 O2 1.291(3) .
C1 C2 1.524(3) .
C2 C3 1.558(3) .
C2 C5 1.581(3) .
C2 H2 1.0000 .
C3 C4 1.521(3) .
C3 C9 1.586(3) .
C3 H3 1.0000 .
C4 O3 1.229(3) .
C4 O4 1.305(3) .
C5 C6 1.533(3) .
C5 C7 1.534(3) .
C5 C8 1.535(3) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C12 1.521(3) .
C9 C11 1.529(3) .
C9 C10 1.533(3) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
Ca1 O1 2.2740(16) .
Ca1 O1 2.2740(16) 3_766
Ca1 O2S 2.3180(18) 3_766
Ca1 O2S 2.3180(18) .
Ca1 O1S 2.3666(16) .
Ca1 O1S 2.3666(16) 3_766
Ca1 H1S 2.79(3) .
Ca1 H3S 2.77(3) .
O2 H4O 1.41(3) .
O4 H4O 1.06(3) .
O1S H1S 0.80(3) .
O1S H2S 0.85(4) .
O2S H3S 0.76(3) .
O2S H4S 0.86(3) .
O3S H5S 0.77(4) .
O3S H6S 0.94(3) .
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
O4 H4O O2 1.06(3) 1.41(3) 2.462(2) 170(3) .
O3S H6S O1 0.94(3) 2.53(3) 3.196(2) 128(2) .
O3S H6S O2 0.94(3) 2.06(4) 2.998(2) 174(3) .
O3S H5S O3 0.77(4) 1.94(4) 2.695(2) 168(4) 2_656
O2S H4S O3 0.86(3) 1.89(3) 2.729(2) 165(3) 2_656
O2S H3S O3S 0.76(3) 1.96(4) 2.684(2) 161(3) 1_655
O1S H2S O2 0.85(4) 2.02(4) 2.869(2) 177(3) 1_655
O1S H1S O3S 0.80(3) 2.02(3) 2.811(3) 166(3) 3_766
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
O1 C1 C2 C3 131.8(2) .
O2 C1 C2 C3 -48.0(3) .
O1 C1 C2 C5 -94.0(2) .
O2 C1 C2 C5 86.2(2) .
C1 C2 C3 C4 72.4(2) .
C5 C2 C3 C4 -60.0(2) .
C1 C2 C3 C9 -58.8(2) .
C5 C2 C3 C9 168.74(17) .
C2 C3 C4 O3 133.3(2) .
C9 C3 C4 O3 -92.8(2) .
C2 C3 C4 O4 -49.1(3) .
C9 C3 C4 O4 84.9(2) .
C1 C2 C5 C6 176.73(18) .
C3 C2 C5 C6 -48.8(2) .
C1 C2 C5 C7 -61.1(2) .
C3 C2 C5 C7 73.3(2) .
C1 C2 C5 C8 59.2(2) .
C3 C2 C5 C8 -166.31(19) .
C4 C3 C9 C12 -52.1(3) .
C2 C3 C9 C12 81.5(2) .
C4 C3 C9 C11 -174.9(2) .
C2 C3 C9 C11 -41.3(3) .
C4 C3 C9 C10 67.2(2) .
C2 C3 C9 C10 -159.2(2) .
O2 C1 O1 Ca1 172.6(15) .
C2 C1 O1 Ca1 -7.3(18) .
O1 Ca1 O1 C1 -140(100) 3_766
O2S Ca1 O1 C1 106.1(17) 3_766
O2S Ca1 O1 C1 -73.9(17) .
O1S Ca1 O1 C1 17.3(17) .
O1S Ca1 O1 C1 -162.7(17) 3_766
