#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/82/2018215.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2018215
loop_
_publ_author_name
'Böhle, Tony'
'Eissmann, Frank'
'Seichter, Wilhelm'
'Weber, Edwin'
'Mertens, Florian O. R. L.'
_publ_section_title
;
 Little change but great effect: varying supramolecular interactions in
 2,5-dimethoxyterephthalic acid and 2,5-diethoxyterephthalic acid
;
_journal_coeditor_code           EG3074
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o350
_journal_page_last               o353
_journal_paper_doi               10.1107/S0108270111030538
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H10 O6'
_chemical_formula_moiety         'C10 H10 O6'
_chemical_formula_sum            'C10 H10 O6'
_chemical_formula_weight         226.18
_chemical_name_common            '2,5-dimethoxyterephthalic acid'
_chemical_name_systematic        '2,5-dimethoxyterephthalic acid'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.804(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6424(3)
_cell_length_b                   10.7368(3)
_cell_length_c                   7.6554(2)
_cell_measurement_reflns_used    2686
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.98
_cell_measurement_theta_min      2.58
_cell_volume                     954.83(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5259
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       piece
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0293
_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)+(0.0531P)²+0.1541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0841
_reflns_number_gt                869
_reflns_number_total             985
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL monoklin_C2c in C2/c
CELL  0.71073  11.6424  10.7368   7.6554   90.000   93.804   90.000
ZERR     4.00   0.0003   0.0003   0.0002    0.000    0.002    0.000
LATT   7
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    O
UNIT  40   40   24
MERG   2
OMIT     0.00  53.00
OMIT     3   5   2
OMIT     3   1   0
OMIT     5   5   0
OMIT     3   3   0
OMIT    -3   3   4
OMIT     9   1   3
EQIV $1 -1/2+x, -1/2+y, z
EQIV $2 1/2-x, -1/2+y, 1/2-z
HTAB O2 O3
HTAB C5 O1_$1
HTAB C5 O1_$2
HTAB O2 O1_$2
MPLA O1 O2 O3 C1 C2 C3 C4 C5
FMAP   2
PLAN   20
SIZE     0.13   0.18   0.45
ACTA
HTAB    2.00000
BOND
BOND   $H
CONF
WGHT     0.05310     0.15410
L.S.  10
TEMP  -120.00
FVAR     0.23511
MOLE    1
O1    3    0.274722    1.056852    0.245443    11.00000    0.02294    0.03279 =
        0.04287    0.00152   -0.01187   -0.00628
O2    3    0.261762    0.853104    0.228941    11.00000    0.02069    0.02891 =
        0.04126    0.00013   -0.00938    0.00088
AFIX  147
H2    2    0.214616    0.799655    0.188097    11.00000   -1.50000
AFIX    0
O3    3    0.076625    0.762006    0.077488    11.00000    0.02338    0.02012 =
        0.03825    0.00062   -0.00960   -0.00151
C1    1    0.105796    0.979126    0.092754    11.00000    0.01525    0.02648 =
        0.01873    0.00076    0.00078   -0.00215
C2    1    0.036301    0.878476    0.036644    11.00000    0.01871    0.02163 =
        0.02049    0.00104    0.00096   -0.00112
C3    1   -0.068760    0.900213   -0.055392    11.00000    0.01785    0.02231 =
        0.02164   -0.00111   -0.00004   -0.00515
AFIX   43
H3    2   -0.115772    0.831754   -0.093174    11.00000   -1.20000
AFIX    0
C4    1    0.220358    0.966823    0.194451    11.00000    0.01729    0.02797 =
        0.02402    0.00109   -0.00137   -0.00291
C5    1    0.007970    0.656316    0.024150    11.00000    0.02899    0.02021 =
        0.03250   -0.00095   -0.00721   -0.00353
AFIX  137
H5A   2   -0.066404    0.661078    0.076695    11.00000   -1.50000
H5B   2    0.047876    0.579818    0.062953    11.00000   -1.50000
H5C   2   -0.004554    0.655712   -0.103707    11.00000   -1.50000
AFIX    0
HKLF    4
END
;
_cod_data_source_file            eg3074.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2018215
_cod_database_fobs_code          2018215
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.27472(6) 1.05685(8) 0.24544(10) 0.0335(2) Uani d . 1 1
O O2 0.26176(6) 0.85310(8) 0.22894(10) 0.0308(2) Uani d . 1 1
H H2 0.2146 0.7997 0.1881 0.046 Uiso calc R 1 1
O O3 0.07663(6) 0.76201(7) 0.07749(9) 0.0278(2) Uani d . 1 1
C C1 0.10580(8) 0.97913(9) 0.09275(11) 0.0202(2) Uani d . 1 1
C C2 0.03630(8) 0.87848(9) 0.03664(12) 0.0203(2) Uani d . 1 1
C C3 -0.06876(8) 0.90021(9) -0.05539(11) 0.0207(2) Uani d . 1 1
H H3 -0.1158 0.8318 -0.0932 0.025 Uiso calc R 1 1
C C4 0.22036(8) 0.96682(10) 0.19445(13) 0.0232(3) Uani d . 1 1
C C5 0.00797(10) 0.65632(10) 0.02415(14) 0.0276(3) Uani d . 1 1
H H5A -0.0664 0.6611 0.0767 0.041 Uiso calc R 1 1
H H5B 0.0479 0.5798 0.0630 0.041 Uiso calc R 1 1
H H5C -0.0046 0.6557 -0.1037 0.041 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0229(4) 0.0328(5) 0.0429(5) -0.0063(3) -0.0119(3) 0.0015(3)
O2 0.0207(4) 0.0289(5) 0.0413(5) 0.0009(3) -0.0094(3) 0.0001(3)
O3 0.0234(4) 0.0201(4) 0.0382(4) -0.0015(3) -0.0096(3) 0.0006(3)
C1 0.0152(5) 0.0265(5) 0.0187(4) -0.0021(4) 0.0008(3) 0.0008(3)
C2 0.0187(5) 0.0216(5) 0.0205(4) -0.0011(4) 0.0010(4) 0.0010(3)
C3 0.0178(5) 0.0223(5) 0.0216(5) -0.0052(4) 0.0000(4) -0.0011(4)
C4 0.0173(5) 0.0280(5) 0.0240(5) -0.0029(4) -0.0014(4) 0.0011(4)
C5 0.0290(6) 0.0202(5) 0.0325(5) -0.0035(4) -0.0072(4) -0.0010(4)
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_site_symmetry_1
_geom_angle
C4 O2 H2 . 109.5
C2 O3 C5 . 118.94(7)
C3 C1 C2 5_575 119.43(9)
C3 C1 C4 5_575 116.15(9)
C2 C1 C4 . 124.41(9)
O3 C2 C3 . 123.21(9)
O3 C2 C1 . 116.99(8)
C3 C2 C1 . 119.80(9)
C1 C3 C2 5_575 120.77(9)
C1 C3 H3 5_575 119.6
C2 C3 H3 . 119.6
O1 C4 O2 . 119.67(9)
O1 C4 C1 . 121.68(9)
O2 C4 C1 . 118.65(8)
O3 C5 H5A . 109.5
O3 C5 H5B . 109.5
H5A C5 H5B . 109.5
O3 C5 H5C . 109.5
H5A C5 H5C . 109.5
H5B C5 H5C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C4 . 1.2061(12)
O2 C4 . 1.3327(13)
O2 H2 . 0.84
O3 C2 . 1.3647(12)
O3 C5 . 1.4318(12)
C1 C3 5_575 1.3891(14)
C1 C2 . 1.4003(14)
C1 C4 . 1.5049(14)
C2 C3 . 1.3902(14)
C3 C1 5_575 1.3891(14)
C3 H3 . 0.95
C5 H5A . 0.98
C5 H5B . 0.98
C5 H5C . 0.98
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 H2 O3 . 0.84 1.81 2.5720(10) 149.8
C5 H5A O1 3_445 0.98 2.58 3.4634(14) 149.9
C5 H5B O1 4_545 0.98 2.46 3.1718(13) 128.7
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
C5 O3 C2 C3 . . -0.21(13)
C5 O3 C2 C1 . . 179.44(8)
C3 C1 C2 O3 5_575 . -179.74(8)
C4 C1 C2 O3 . . -0.24(14)
C3 C1 C2 C3 5_575 . -0.07(15)
C4 C1 C2 C3 . . 179.43(8)
O3 C2 C3 C1 . 5_575 179.72(8)
C1 C2 C3 C1 . 5_575 0.08(15)
C3 C1 C4 O1 5_575 . 2.44(14)
C2 C1 C4 O1 . . -177.08(9)
C3 C1 C4 O2 5_575 . -177.85(8)
C2 C1 C4 O2 . . 2.64(15)
