#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:30:43 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179634 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/98/4509827.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509827
loop_
_publ_author_name
'Kohmoto, Shigeo'
'Kuroda, Yu'
'Kishikawa, Keiki'
'Masu, Hyuma'
'Azumaya, Isao'
_publ_section_title
;
 Generation of Square-Shaped Cyclic Dimers vs Zigzag Hydrogen-Bonding
 Networks and Pseudoconformational Polymorphism of Tethered Benzoic Acids
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5017
_journal_paper_doi               10.1021/cg901244v
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C21 H24 O8, 2(C1 H4 O)'
_chemical_formula_sum            'C23 H32 O10'
_chemical_formula_weight         468.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 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                 113.219(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   18.241(8)
_cell_length_b                   4.4906(19)
_cell_length_c                   15.404(7)
_cell_measurement_reflns_used    1013
_cell_measurement_temperature    90
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      2.65
_cell_volume                     1159.6(9)
_computing_cell_refinement       'Bruker Smart'
_computing_data_collection       'Bruker Smart'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'Bruker Smart1000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_sigmaI/netI    0.0995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6257
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9691
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1176P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.2079
_reflns_number_gt                1496
_reflns_number_total             2687
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg901244vsup1.cif
_cod_data_source_block           1-MeOH(810gmas)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2/c  '
_cod_database_code               4509827
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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 0.36350(17) 0.6149(7) 0.55590(19) 0.0237(7) Uani 1 1 d .
C2 C 0.29133(16) 0.7402(6) 0.56479(18) 0.0198(6) Uani 1 1 d .
C3 C 0.27139(16) 0.6575(6) 0.64038(17) 0.0196(6) Uani 1 1 d .
H3 H 0.3042 0.5241 0.6876 0.024 Uiso 1 1 calc R
C4 C 0.20299(16) 0.7743(6) 0.64451(17) 0.0185(6) Uani 1 1 d .
C5 C 0.15487(16) 0.9748(6) 0.57630(17) 0.0193(6) Uani 1 1 d .
H5 H 0.1084 1.0563 0.5807 0.023 Uiso 1 1 calc R
C6 C 0.17596(16) 1.0527(6) 0.50221(17) 0.0176(6) Uani 1 1 d .
C7 C 0.24461(17) 0.9365(6) 0.49669(18) 0.0204(7) Uani 1 1 d .
H7 H 0.2593 0.9922 0.4462 0.024 Uiso 1 1 calc R
C8 C 0.22180(18) 0.5082(7) 0.78651(18) 0.0254(7) Uani 1 1 d .
H8A H 0.2235 0.3133 0.7588 0.038 Uiso 1 1 calc R
H8B H 0.1975 0.4875 0.8327 0.038 Uiso 1 1 calc R
H8C H 0.2762 0.5858 0.8180 0.038 Uiso 1 1 calc R
C9 C 0.05840(16) 1.3548(6) 0.42804(17) 0.0204(7) Uani 1 1 d .
H9A H 0.0666 1.4781 0.4844 0.024 Uiso 1 1 calc R
H9B H 0.0224 1.1877 0.4261 0.024 Uiso 1 1 calc R
C10 C 0.02299(17) 1.5400(6) 0.33942(17) 0.0209(7) Uani 1 1 d .
H10A H 0.0622 1.6931 0.3397 0.025 Uiso 1 1 calc R
H10B H -0.0250 1.6441 0.3391 0.025 Uiso 1 1 calc R
C11 C 0.0000 1.3534(9) 0.2500 0.0199(9) Uani 1 2 d S
H11A H -0.0455 1.2234 0.2445 0.024 Uiso 0.50 1 calc PR
H11B H 0.0455 1.2234 0.2555 0.024 Uiso 0.50 1 calc PR
C12 C 0.4262(2) 1.0082(8) 0.3326(2) 0.0377(9) Uani 1 1 d .
H12A H 0.4153 1.1758 0.3666 0.057 Uiso 1 1 calc R
H12B H 0.3759 0.9109 0.2935 0.057 Uiso 1 1 calc R
H12C H 0.4525 1.0814 0.2923 0.057 Uiso 1 1 calc R
O1 O 0.37739(12) 0.6527(5) 0.48550(13) 0.0320(6) Uani 1 1 d .
O2 O 0.40926(12) 0.4562(5) 0.62892(13) 0.0307(6) Uani 1 1 d .
H2 H 0.4449 0.3720 0.6162 0.046 Uiso 1 1 calc R
O3 O 0.17532(11) 0.7100(5) 0.71350(12) 0.0250(5) Uani 1 1 d .
O4 O 0.13348(11) 1.2436(4) 0.43159(12) 0.0216(5) Uani 1 1 d .
O5 O 0.47593(14) 0.8034(6) 0.39773(16) 0.0471(7) Uani 1 1 d .
H5A H 0.4527 0.7365 0.4311 0.071 Uiso 1 1 calc R
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'
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 123.5(3) . .
O1 C1 C2 122.1(3) . .
O2 C1 C2 114.4(2) . .
C7 C2 C3 121.2(3) . .
C7 C2 C1 118.4(2) . .
C3 C2 C1 120.4(3) . .
C4 C3 C2 118.3(3) . .
C4 C3 H3 120.8 . .
C2 C3 H3 120.8 . .
O3 C4 C3 124.8(3) . .
O3 C4 C5 113.8(2) . .
C3 C4 C5 121.4(2) . .
C6 C5 C4 119.0(2) . .
C6 C5 H5 120.5 . .
C4 C5 H5 120.5 . .
O4 C6 C5 124.2(2) . .
O4 C6 C7 115.5(2) . .
C5 C6 C7 120.3(3) . .
C2 C7 C6 119.7(2) . .
C2 C7 H7 120.2 . .
C6 C7 H7 120.2 . .
O3 C8 H8A 109.5 . .
O3 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
O3 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O4 C9 C10 106.7(2) . .
O4 C9 H9A 110.4 . .
C10 C9 H9A 110.4 . .
O4 C9 H9B 110.4 . .
C10 C9 H9B 110.4 . .
H9A C9 H9B 108.6 . .
C9 C10 C11 112.5(2) . .
C9 C10 H10A 109.1 . .
C11 C10 H10A 109.1 . .
C9 C10 H10B 109.1 . .
C11 C10 H10B 109.1 . .
H10A C10 H10B 107.8 . .
C10 C11 C10 113.2(3) . 2
C10 C11 H11A 108.9 . .
C10 C11 H11A 108.9 2 .
C10 C11 H11B 108.9 . .
C10 C11 H11B 108.9 2 .
H11A C11 H11B 107.7 . .
O5 C12 H12A 109.5 . .
O5 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
O5 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C1 O2 H2 109.5 . .
C4 O3 C8 117.1(2) . .
C6 O4 C9 118.85(19) . .
C12 O5 H5A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.219(3) .
C1 O2 1.315(3) .
C1 C2 1.487(4) .
C2 C7 1.378(4) .
C2 C3 1.400(3) .
C3 C4 1.378(4) .
C3 H3 0.9500 .
C4 O3 1.375(3) .
C4 C5 1.399(4) .
C5 C6 1.385(3) .
C5 H5 0.9500 .
C6 O4 1.361(3) .
C6 C7 1.390(4) .
C7 H7 0.9500 .
C8 O3 1.433(3) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 O4 1.438(3) .
C9 C10 1.509(4) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.523(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C10 1.523(3) 2
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 O5 1.399(4) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
O2 H2 0.8400 .
O5 H5A 0.8400 .
