#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:12:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180128 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/26/7102656.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_7102656
loop_
_publ_author_name
'Dale, Sophie H'
'Elsegood, Mark R J'
'Richards, Simon J'
_publ_section_title
;
 Step-wise dis-assembly of trimesic acid: mono- and bis(methanol)
 solvates.
;
_journal_issue                   11
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1278
_journal_page_last               1279
_journal_paper_doi               10.1039/b402922d
_journal_year                    2004
_chemical_formula_sum            'C11 H14 O8'
_chemical_formula_weight         274.22
_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                91.206(6)
_cell_angle_beta                 91.881(6)
_cell_angle_gamma                93.998(5)
_cell_formula_units_Z            2
_cell_length_a                   3.7519(9)
_cell_length_b                   9.579(2)
_cell_length_c                   17.732(4)
_cell_measurement_reflns_used    2968
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      2.13
_cell_volume                     635.2(3)
_computing_cell_refinement       'local programs'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3936
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.15
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.058(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.227
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0780
_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)+(0.0139P)²+2.2603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.1816
_reflns_number_gt                1803
_reflns_number_total             2215
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b402922d.txt
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7102656
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9223(11) 0.2483(4) 0.3093(2) 0.0216(9) Uani 1 1 d . . .
H1A H 1.0429 0.2474 0.3572 0.026 Uiso 1 1 calc R . .
C2 C 0.8149(11) 0.1231(4) 0.2714(2) 0.0221(9) Uani 1 1 d . . .
C3 C 0.6492(11) 0.1257(4) 0.2006(2) 0.0226(10) Uani 1 1 d . . .
H3 H 0.5822 0.0401 0.1742 0.027 Uiso 1 1 calc R . .
C4 C 0.5793(11) 0.2519(4) 0.1675(2) 0.0209(9) Uani 1 1 d . . .
C5 C 0.6836(11) 0.3763(4) 0.2058(2) 0.0223(10) Uani 1 1 d . . .
H5 H 0.6399 0.4631 0.1836 0.027 Uiso 1 1 calc R . .
C6 C 0.8529(11) 0.3745(4) 0.2770(2) 0.0224(9) Uani 1 1 d . . .
C7 C 0.3967(12) 0.2532(4) 0.0916(2) 0.0247(10) Uani 1 1 d . . .
O1 O 0.3195(10) 0.1375(3) 0.05827(18) 0.0392(9) Uani 1 1 d . . .
H1 H 0.2146 0.1506 0.0167 0.059 Uiso 0.507(8) 1 calc PR A 1
O2 O 0.3278(10) 0.3698(3) 0.06466(18) 0.0366(9) Uani 1 1 d . . .
H2 H 0.2412 0.3574 0.0205 0.055 Uiso 0.493(8) 1 calc PR A 2
C8 C 0.8965(12) -0.0129(4) 0.3063(2) 0.0254(10) Uani 1 1 d . . .
O3 O 0.7569(10) -0.1211(3) 0.26654(19) 0.0363(9) Uani 1 1 d . . .
H3A H 0.810(15) -0.201(6) 0.287(3) 0.055 Uiso 1 1 d . . .
O4 O 1.0696(9) -0.0190(3) 0.36486(17) 0.0311(8) Uani 1 1 d . . .
C9 C 0.9679(12) 0.5125(4) 0.3161(2) 0.0257(10) Uani 1 1 d . . .
O5 O 1.1381(10) 0.5014(3) 0.38096(18) 0.0349(9) Uani 1 1 d . . .
H5A H 1.2315 0.5803 0.3951 0.052 Uiso 1 1 calc R . .
O6 O 0.9035(10) 0.6216(3) 0.28764(19) 0.0394(9) Uani 1 1 d . . .
O7 O 1.3593(11) -0.2507(3) 0.42785(19) 0.0418(10) Uani 1 1 d . . .
H7 H 1.2604 -0.1826 0.4093 0.063 Uiso 1 1 calc R . .
C10 C 1.5150(15) -0.2110(6) 0.4992(3) 0.0446(14) Uani 1 1 d . . .
H10A H 1.7071 -0.1378 0.4933 0.067 Uiso 1 1 calc R . .
H10B H 1.6133 -0.2924 0.5226 0.067 Uiso 1 1 calc R . .
H10C H 1.3326 -0.1753 0.5314 0.067 Uiso 1 1 calc R . .
C11A C -0.1556(15) 0.2541(6) -0.1003(3) 0.0433(13) Uani 0.507(8) 1 d P A 1
H11A H -0.4131 0.2422 -0.0924 0.065 Uiso 0.507(8) 1 calc PR A 1
H11B H -0.1146 0.2644 -0.1543 0.065 Uiso 0.507(8) 1 calc PR A 1
H11C H -0.0541 0.3379 -0.0726 0.065 Uiso 0.507(8) 1 calc PR A 1
O8A O 0.025(2) 0.1251(7) -0.0717(4) 0.039(2) Uani 0.507(8) 1 d P A 1
H8A H -0.1308 0.0588 -0.0670 0.058 Uiso 0.507(8) 1 calc PR A 1
C11B C -0.1556(15) 0.2541(6) -0.1003(3) 0.0433(13) Uani 0.493(8) 1 d P A 2
H11D H 0.0202 0.1851 -0.1094 0.065 Uiso 0.493(8) 1 calc PR A 2
H11E H -0.2702 0.2776 -0.1484 0.065 Uiso 0.493(8) 1 calc PR A 2
H11F H -0.3373 0.2148 -0.0668 0.065 Uiso 0.493(8) 1 calc PR A 2
O8B O 0.027(2) 0.3824(7) -0.0646(4) 0.038(2) Uani 0.493(8) 1 d P A 2
H8B H -0.1200 0.4443 -0.0606 0.057 Uiso 0.493(8) 1 calc PR A 2
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
C6 C1 C2 119.8(4)
C3 C2 C1 119.6(4)
C3 C2 C8 120.9(4)
C1 C2 C8 119.4(4)
C2 C3 C4 121.0(4)
C5 C4 C3 119.1(4)
C5 C4 C7 120.4(4)
C3 C4 C7 120.4(4)
C4 C5 C6 120.2(4)
C1 C6 C5 120.2(4)
C1 C6 C9 121.3(4)
C5 C6 C9 118.4(4)
O1 C7 O2 123.9(4)
O1 C7 C4 117.7(4)
O2 C7 C4 118.4(4)
O4 C8 O3 125.0(4)
O4 C8 C2 122.8(4)
O3 C8 C2 112.2(4)
O6 C9 O5 124.8(4)
O6 C9 C6 120.8(4)
O5 C9 C6 114.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.386(6)
C1 C2 1.391(6)
C2 C3 1.384(6)
C2 C8 1.500(6)
C3 C4 1.392(6)
C4 C5 1.385(6)
C4 C7 1.492(6)
C5 C6 1.395(6)
C6 C9 1.509(6)
C7 O1 1.255(5)
C7 O2 1.264(5)
C8 O4 1.212(5)
C8 O3 1.309(5)
C9 O6 1.206(5)
C9 O5 1.307(5)
O7 C10 1.410(6)
C11A O8A 1.537(8)
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
O1 H1 O8A 0.84 1.71 2.521(7) 162.6 .
O2 H2 O8B 0.84 1.72 2.531(7) 162.7 .
O7 H7 O4 0.84 1.94 2.777(4) 175.4 .
O3 H3A O6 0.88(6) 1.76(6) 2.594(4) 156(6) 1_545
O5 H5A O7 0.84 1.74 2.572(4) 171.3 1_565
O8A H8A O1 0.84 1.97 2.765(7) 156.8 2
O8B H8B O2 0.84 2.00 2.801(7) 160.4 2_565
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
C6 C1 C2 C3 2.0(6)
C6 C1 C2 C8 179.0(4)
C1 C2 C3 C4 -1.8(7)
C8 C2 C3 C4 -178.8(4)
C2 C3 C4 C5 1.2(6)
C2 C3 C4 C7 -179.3(4)
C3 C4 C5 C6 -0.7(6)
C7 C4 C5 C6 179.7(4)
C2 C1 C6 C5 -1.6(6)
C2 C1 C6 C9 -179.5(4)
C4 C5 C6 C1 0.9(6)
C4 C5 C6 C9 178.9(4)
C5 C4 C7 O1 177.5(4)
C3 C4 C7 O1 -2.1(6)
C5 C4 C7 O2 -2.7(6)
C3 C4 C7 O2 177.7(4)
C3 C2 C8 O4 173.1(4)
C1 C2 C8 O4 -3.9(7)
C3 C2 C8 O3 -7.5(6)
C1 C2 C8 O3 175.5(4)
C1 C6 C9 O6 -179.4(5)
C5 C6 C9 O6 2.6(7)
C1 C6 C9 O5 0.8(6)
C5 C6 C9 O5 -177.2(4)
