#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/91/2239164.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_2239164
loop_
_publ_author_name
'Uchida, Akira'
'Hasegawa, Masatoshi'
'Yamaguchi, Shinya'
'Takezawa, Eiichiro'
'Ishikawa, Atsushi'
'Kagayama, Takashi'
_publ_section_title
;
 (1S*,2S*,4R*,5R*)-Cyclohexane-1,2,4,5-tetracarboxylic
 acid
;
_journal_coeditor_code           IS5327
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o75
_journal_paper_doi               10.1107/S1600536813033795
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C10 H12 O8'
_chemical_formula_moiety         'C10 H12 O8'
_chemical_formula_sum            'C10 H12 O8'
_chemical_formula_weight         260.20
_chemical_name_systematic
'(1S*,2S*,4R*,5R*)-Cyclohexane-1,2,4,5-tetracarboxylic acid'
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   17.6970(6)
_cell_length_b                   17.6970(6)
_cell_length_c                   9.5455(6)
_cell_measurement_reflns_used    2340
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.30
_cell_volume                     2589.0(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek,
2009)
;
_computing_publication_material  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Bruker APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6439
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_min         2.302
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0607P)²+1.9122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                1388
_reflns_number_total             1653
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5327sup1.cif
_cod_data_source_block           I
_cod_database_code               2239164
_cod_database_fobs_code          2239164
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.966
_shelxl_version_number           .2013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.51496(8) 0.07671(7) -0.08154(11) 0.0279(3) Uani d 1
H H1A 0.4929 0.1116 -0.1242 0.034 Uiso calc 1
H H1B 0.5770 0.1045 -0.1011 0.034 Uiso calc 1
C C2 0.50063(7) 0.07293(7) 0.07787(11) 0.0233(2) Uani d 1
H H2 0.4383 0.0484 0.0969 0.028 Uiso calc 1
C C3 0.53165(7) 0.01523(7) 0.14585(11) 0.0242(2) Uani d 1
H H3 0.5944 0.0414 0.1285 0.029 Uiso calc 1
C C4 0.55013(8) 0.16503(7) 0.13456(12) 0.0283(3) Uani d 1
C C5 0.51702(8) 0.00882(8) 0.30236(12) 0.0267(3) Uani d 1
O O1 0.62253(6) 0.19739(7) 0.18327(13) 0.0471(3) Uani d 1
H H4 0.5352(17) 0.2558(18) 0.151(3) 0.083(8) Uiso d 1
O O2 0.50596(8) 0.20615(8) 0.12244(15) 0.0543(3) Uani d 1
O O3 0.46919(7) 0.03210(7) 0.35746(9) 0.0380(3) Uani d 1
O O4 0.55716(7) -0.02417(7) 0.37025(10) 0.0400(3) Uani d 1
H H5 0.5485(19) -0.0245(19) 0.467(3) 0.110(10) Uiso d 1
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 6.1.1.4 and Sasaki (1989)'
H H 0.0000 0.0000 'International Tables Vol C Tables 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 6.1.1.4 and Sasaki (1989)'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C3 C1 C2 10_655 . 111.06(9)
C3 C1 H1A 10_655 . 109.4
C2 C1 H1A . . 109.4
C3 C1 H1B 10_655 . 109.4
C2 C1 H1B . . 109.4
H1A C1 H1B . . 108.0
C4 C2 C3 . . 111.15(9)
C4 C2 C1 . . 108.23(9)
C3 C2 C1 . . 110.07(9)
C4 C2 H2 . . 109.1
C3 C2 H2 . . 109.1
C1 C2 H2 . . 109.1
C5 C3 C2 . . 111.43(9)
C5 C3 C1 . 10_655 109.53(9)
C2 C3 C1 . 10_655 110.89(9)
C5 C3 H3 . . 108.3
C2 C3 H3 . . 108.3
C1 C3 H3 10_655 . 108.3
O1 C4 O2 . . 123.84(12)
O1 C4 C2 . . 123.74(11)
O2 C4 C2 . . 112.41(11)
O3 C5 O4 . . 124.14(11)
O3 C5 C3 . . 121.25(10)
O4 C5 C3 . . 114.60(10)
C4 O2 H4 . . 109.5(18)
C5 O4 H5 . . 111.8(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C3 10_655 1.5370(16)
C1 C2 . 1.5386(15)
C1 H1A . 0.9700
C1 H1B . 0.9700
C2 C4 . 1.5130(15)
C2 C3 . 1.5251(15)
C2 H2 . 0.9800
C3 C5 . 1.5108(15)
C3 H3 . 0.9800
C4 O1 . 1.2049(16)
C4 O2 . 1.3126(16)
C5 O3 . 1.2295(15)
C5 O4 . 1.2961(14)
O2 H4 . 0.81(3)
O4 H5 . 0.94(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H4 O1 3_665 0.81(3) 1.93(3) 2.705(2) 160(3)
O4 H5 O3 10_656 0.94(3) 1.70(3) 2.6320(10) 176(3)
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C3 C1 C2 C4 10_655 . 178.45(9)
C3 C1 C2 C3 10_655 . 56.81(13)
C4 C2 C3 C5 . . 61.11(12)
C1 C2 C3 C5 . . -179.00(9)
C4 C2 C3 C1 . 10_655 -176.60(9)
C1 C2 C3 C1 . 10_655 -56.70(13)
C3 C2 C4 O1 . . 25.59(16)
C1 C2 C4 O1 . . -95.39(14)
C3 C2 C4 O2 . . -155.53(11)
C1 C2 C4 O2 . . 83.49(13)
C2 C3 C5 O3 . . 14.47(16)
C1 C3 C5 O3 10_655 . -108.61(13)
C2 C3 C5 O4 . . -166.81(10)
C1 C3 C5 O4 10_655 . 70.12(13)
