#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:12:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179656 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/09/4510991.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_4510991
loop_
_publ_author_name
'Varughese, Sunil'
'Desiraju, Gautam R.'
_publ_section_title
;
 Using Water as a Design Element in Crystal Engineering. Host−Guest
 Compounds of Hydrated 3,5-Dihydroxybenzoic Acid
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4184
_journal_paper_doi               10.1021/cg100872w
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         '2(C7 H6 O4), 0.5(C4 H6 O4), 2(H2 O)'
_chemical_formula_sum            'C16 H19 O12'
_chemical_formula_weight         403.31
_chemical_name_common            '3,5-Dihydroxybenzoic acid dimethyloxalate'
_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                99.12(3)
_cell_angle_beta                 93.63(3)
_cell_angle_gamma                110.63(3)
_cell_formula_units_Z            2
_cell_length_a                   7.254(2)
_cell_length_b                   9.334(2)
_cell_length_c                   14.517(3)
_cell_measurement_reflns_used    894
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      46.23
_cell_measurement_theta_min      4.72
_cell_volume                     900.7(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_molecular_graphics    'Material Studio 4.4'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from 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  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7814
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private commounication'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blocks
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0968
_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)+(0.0674P)²+6.9362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2907
_refine_ls_wR_factor_ref         0.2951
_reflns_number_gt                2554
_reflns_number_total             3201
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            03_dimethyloxalate.CIF
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_database_code               4510991
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
O23 O 0.2605(7) 0.5196(5) 0.0012(3) 0.0285(11) Uani 1 1 d .
H23 H 0.2844 0.4628 0.0361 0.043 Uiso 1 1 calc R
O25 O 0.2498(7) 1.0331(5) 0.0156(3) 0.0263(10) Uani 1 1 d .
H25 H 0.2012 0.9945 -0.0408 0.039 Uiso 1 1 calc R
O27A O 0.5541(7) 0.8062(5) 0.3332(3) 0.0277(11) Uani 1 1 d .
H27 H 0.6088 0.8460 0.3887 0.042 Uiso 1 1 calc R
O27B O 0.5892(7) 1.0548(5) 0.3308(3) 0.0305(11) Uani 1 1 d .
C21 C 0.4384(9) 0.8637(7) 0.1917(4) 0.0195(12) Uani 1 1 d .
C22 C 0.3953(9) 0.7111(7) 0.1452(4) 0.0191(12) Uani 1 1 d .
H22 H 0.4278 0.6389 0.1759 0.023 Uiso 1 1 calc R
C23 C 0.3038(9) 0.6668(7) 0.0529(4) 0.0211(13) Uani 1 1 d .
C24 C 0.2551(9) 0.7730(7) 0.0077(4) 0.0216(13) Uani 1 1 d .
H24 H 0.1930 0.7420 -0.0556 0.026 Uiso 1 1 calc R
C25 C 0.2984(9) 0.9239(7) 0.0563(4) 0.0189(12) Uani 1 1 d .
C26 C 0.3934(8) 0.9729(7) 0.1476(4) 0.0192(12) Uani 1 1 d .
H26 H 0.4274 1.0775 0.1795 0.023 Uiso 1 1 calc R
C27 C 0.5337(9) 0.9125(7) 0.2922(4) 0.0193(12) Uani 1 1 d .
O13 O -0.1162(7) 0.5511(5) 0.1824(3) 0.0268(11) Uani 1 1 d .
H13 H -0.1593 0.5375 0.1253 0.040 Uiso 1 1 calc R
O15 O -0.0882(7) 1.0672(5) 0.1702(3) 0.0243(10) Uani 1 1 d .
H15 H -0.0303 1.1596 0.1993 0.036 Uiso 1 1 calc R
O17A O 0.2266(7) 0.8560(5) 0.4972(3) 0.0288(11) Uani 1 1 d .
H17 H 0.2868 0.8977 0.5516 0.043 Uiso 1 1 calc R
O17B O 0.2578(7) 1.1041(5) 0.4946(3) 0.0266(10) Uani 1 1 d .
C11 C 0.0943(9) 0.9101(7) 0.3578(4) 0.0191(12) Uani 1 1 d .
C12 C 0.0389(9) 0.7537(7) 0.3133(4) 0.0187(12) Uani 1 1 d .
H12 H 0.0692 0.6814 0.3449 0.022 Uiso 1 1 calc R
C13 C -0.0605(9) 0.7063(7) 0.2230(4) 0.0187(12) Uani 1 1 d .
C14 C -0.1019(8) 0.8118(7) 0.1752(4) 0.0174(12) Uani 1 1 d .
H14 H -0.1697 0.7780 0.1129 0.021 Uiso 1 1 calc R
C15 C -0.0428(9) 0.9677(7) 0.2198(4) 0.0193(12) Uani 1 1 d .
C16 C 0.0542(8) 1.0175(6) 0.3123(4) 0.0167(12) Uani 1 1 d .
H16 H 0.0917 1.1231 0.3433 0.020 Uiso 1 1 calc R
C17 C 0.1995(9) 0.9600(7) 0.4562(4) 0.0194(12) Uani 1 1 d .
O32 O 0.8086(7) 0.5341(6) 0.5566(3) 0.0331(12) Uani 1 1 d .
O33 O 0.8165(6) 0.4421(5) 0.4040(3) 0.0268(10) Uani 1 1 d .
C31 C 0.8917(9) 0.4961(7) 0.4935(4) 0.0229(13) Uani 1 1 d .
C34 C 0.6125(10) 0.4319(10) 0.3802(5) 0.0380(17) Uani 1 1 d .
H34B H 0.5711 0.3914 0.3126 0.057 Uiso 1 1 calc R
H34C H 0.6060 0.5358 0.3964 0.057 Uiso 1 1 calc R
H34A H 0.5239 0.3616 0.4156 0.057 Uiso 1 1 calc R
O90 O 0.0765(8) 0.3680(5) 0.2467(3) 0.0288(11) Uani 1 1 d D
H90A H 0.033(17) 0.435(10) 0.234(8) 0.09(4) Uiso 1 1 d D
H90B H 0.143(16) 0.399(14) 0.299(4) 0.10(4) Uiso 1 1 d D
O93 O 0.6630(8) 0.6602(5) -0.1107(3) 0.0320(11) Uani 1 1 d D
H93A H 0.680(15) 0.752(4) -0.090(7) 0.07(3) Uiso 1 1 d D
H93B H 0.734(10) 0.661(9) -0.153(4) 0.04(2) 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'
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_3
C23 O23 H23 109.5 .
C25 O25 H25 109.5 .
C27 O27A H27 109.5 .
C22 C21 C26 121.8(5) .
C22 C21 C27 119.1(5) .
C26 C21 C27 119.1(5) .
C23 C22 C21 118.5(5) .
C23 C22 H22 120.8 .
C21 C22 H22 120.8 .
O23 C23 C22 122.2(5) .
O23 C23 C24 117.0(5) .
C22 C23 C24 120.8(5) .
C25 C24 C23 119.3(5) .
C25 C24 H24 120.3 .
C23 C24 H24 120.3 .
C26 C25 C24 121.4(5) .
C26 C25 O25 116.8(5) .
C24 C25 O25 121.8(5) .
C25 C26 C21 118.2(5) .
C25 C26 H26 120.9 .
C21 C26 H26 120.9 .
O27B C27 O27A 124.2(5) .
O27B C27 C21 118.4(5) .
O27A C27 C21 117.4(5) .
C13 O13 H13 109.5 .
C15 O15 H15 109.5 .
C17 O17A H17 109.5 .
C16 C11 C12 121.3(5) .
C16 C11 C17 120.1(5) .
C12 C11 C17 118.6(5) .
C13 C12 C11 118.9(5) .
C13 C12 H12 120.5 .
C11 C12 H12 120.5 .
O13 C13 C12 117.3(5) .
O13 C13 C14 121.6(5) .
C12 C13 C14 121.1(5) .
C13 C14 C15 119.3(5) .
C13 C14 H14 120.4 .
C15 C14 H14 120.4 .
O15 C15 C14 117.2(5) .
O15 C15 C16 122.2(5) .
C14 C15 C16 120.5(5) .
C11 C16 C15 118.8(5) .
C11 C16 H16 120.6 .
C15 C16 H16 120.6 .
O17B C17 O17A 123.6(5) .
O17B C17 C11 118.2(5) .
O17A C17 C11 118.2(5) .
C31 O33 C34 115.8(5) .
O32 C31 O33 126.7(6) .
O32 C31 C31 123.9(7) 2_766
O33 C31 C31 109.5(6) 2_766
O33 C34 H34B 109.5 .
O33 C34 H34C 109.5 .
H34B C34 H34C 109.5 .
O33 C34 H34A 109.5 .
H34B C34 H34A 109.5 .
H34C C34 H34A 109.5 .
H90A O90 H90B 110(10) .
H93A O93 H93B 107(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O23 C23 1.374(7) .
O23 H23 0.8400 .
O25 C25 1.389(7) .
O25 H25 0.8400 .
O27A C27 1.281(7) .
O27A H27 0.8400 .
O27B C27 1.265(7) .
C21 C22 1.392(8) .
C21 C26 1.404(8) .
C21 C27 1.500(8) .
C22 C23 1.387(8) .
C22 H22 0.9500 .
C23 C24 1.401(8) .
C24 C25 1.388(8) .
C24 H24 0.9500 .
C25 C26 1.382(8) .
C26 H26 0.9500 .
O13 C13 1.377(7) .
O13 H13 0.8400 .
O15 C15 1.374(7) .
O15 H15 0.8400 .
O17A C17 1.280(7) .
O17A H17 0.8400 .
O17B C17 1.276(7) .
C11 C16 1.384(8) .
C11 C12 1.402(8) .
C11 C17 1.497(8) .
C12 C13 1.382(8) .
C12 H12 0.9500 .
C13 C14 1.393(8) .
C14 C15 1.395(8) .
C14 H14 0.9500 .
C15 C16 1.403(8) .
C16 H16 0.9500 .
O32 C31 1.203(8) .
O33 C31 1.323(8) .
O33 C34 1.464(8) .
C31 C31 1.545(12) 2_766
C34 H34B 0.9800 .
C34 H34C 0.9800 .
C34 H34A 0.9800 .
O90 H90A 0.83(2) .
O90 H90B 0.83(2) .
O93 H93A 0.83(2) .
O93 H93B 0.82(2) .
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_4
C26 C21 C22 C23 -0.6(9) .
C27 C21 C22 C23 178.8(5) .
C21 C22 C23 O23 178.4(6) .
C21 C22 C23 C24 -0.3(9) .
O23 C23 C24 C25 -179.1(5) .
C22 C23 C24 C25 -0.3(9) .
C23 C24 C25 C26 1.7(9) .
C23 C24 C25 O25 -178.6(6) .
C24 C25 C26 C21 -2.5(9) .
O25 C25 C26 C21 177.8(5) .
C22 C21 C26 C25 1.9(9) .
C27 C21 C26 C25 -177.4(5) .
C22 C21 C27 O27B 173.4(6) .
C26 C21 C27 O27B -7.2(8) .
C22 C21 C27 O27A -6.4(8) .
C26 C21 C27 O27A 173.0(5) .
C16 C11 C12 C13 -1.1(9) .
C17 C11 C12 C13 179.2(5) .
C11 C12 C13 O13 -178.7(5) .
C11 C12 C13 C14 1.5(9) .
O13 C13 C14 C15 179.8(5) .
C12 C13 C14 C15 -0.4(9) .
C13 C14 C15 O15 -179.5(5) .
C13 C14 C15 C16 -1.1(9) .
C12 C11 C16 C15 -0.4(9) .
C17 C11 C16 C15 179.4(5) .
O15 C15 C16 C11 179.8(5) .
C14 C15 C16 C11 1.5(9) .
C16 C11 C17 O17B -3.0(8) .
C12 C11 C17 O17B 176.8(6) .
C16 C11 C17 O17A 177.1(6) .
C12 C11 C17 O17A -3.1(8) .
C34 O33 C31 O32 1.6(9) .
C34 O33 C31 C31 -178.5(6) 2_766
