#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/84/2208408.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_2208408
loop_
_publ_author_name
'Ghulam Qadeer'
'Nasim Hasan Rama'
'Qing-Shan Li'
_publ_section_title
;
 2-(Carboxymethyl)-4,6-dimethoxybenzoic acid
;
_journal_coeditor_code           RZ6167
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o906
_journal_page_last               o907
_journal_paper_doi               10.1107/S1600536806003345
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H12 O6'
_chemical_formula_moiety         'C11 H12 O6'
_chemical_formula_sum            'C11 H12 O6'
_chemical_formula_weight         240.21
_chemical_melting_point          170
_chemical_name_common
;
3,5-dimthoxyhomophthalic acid
;
_chemical_name_systematic
;
2-(Carboxymethyl)-4,6-dimethoxybenzoic acid
;
_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
_cell_angle_alpha                105.937(2)
_cell_angle_beta                 103.444(2)
_cell_angle_gamma                93.211(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2886(10)
_cell_length_b                   7.9631(11)
_cell_length_c                   10.2758(14)
_cell_measurement_reflns_used    2688
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.68
_cell_volume                     553.17(13)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART 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  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4782
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_correction_T_min  0.9660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0437
_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)+(0.0658P)²+0.0652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                2074
_reflns_number_total             2380
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6167.cif
_cod_data_source_block           I
_cod_database_code               2208408
_cod_database_fobs_code          2208408
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
C1 0.28940(18) 0.75801(16) 0.68898(14) 0.0361(3) Uani d . 1 C
C2 0.10780(19) 0.81130(16) 0.68927(13) 0.0364(3) Uani d . 1 C
C3 -0.02643(18) 0.77948(17) 0.55930(14) 0.0368(3) Uani d . 1 C
C4 0.01674(18) 0.69458(18) 0.43471(14) 0.0382(3) Uani d . 1 C
H4 -0.0734 0.6736 0.3496 0.046 Uiso calc R 1 H
C5 0.19461(19) 0.64154(17) 0.43824(14) 0.0375(3) Uani d . 1 C
C6 0.33021(19) 0.67400(17) 0.56503(14) 0.0383(3) Uani d . 1 C
H6 0.4498 0.6385 0.5661 0.046 Uiso calc R 1 H
C7 0.4516(2) 0.80226(18) 0.82010(15) 0.0422(3) Uani d . 1 C
H7A 0.5705 0.8107 0.7938 0.051 Uiso calc R 1 H
H7B 0.4420 0.9171 0.8803 0.051 Uiso calc R 1 H
C8 0.45863(19) 0.67338(17) 0.90187(14) 0.0395(3) Uani d . 1 C
C9 0.0631(2) 0.89595(17) 0.82393(14) 0.0400(3) Uani d . 1 C
C10 -0.3249(2) 0.8280(2) 0.43127(17) 0.0485(4) Uani d . 1 C
H10A -0.2602 0.8918 0.3847 0.073 Uiso calc R 1 H
H10B -0.4348 0.8822 0.4483 0.073 Uiso calc R 1 H
H10C -0.3638 0.7084 0.3733 0.073 Uiso calc R 1 H
C11 0.1312(3) 0.5536(3) 0.18904(16) 0.0577(4) Uani d . 1 C
H11A 0.0121 0.4829 0.1722 0.087 Uiso calc R 1 H
H11B 0.1926 0.5036 0.1168 0.087 Uiso calc R 1 H
H11C 0.1088 0.6711 0.1887 0.087 Uiso calc R 1 H
O1 0.57813(17) 0.73299(14) 1.02706(11) 0.0586(3) Uani d D 1 O
H1 0.591(3) 0.649(2) 1.064(2) 0.088 Uiso d D 1 H
O2 0.37228(14) 0.52591(12) 0.85679(10) 0.0478(3) Uani d . 1 O
O3 0.13985(17) 0.86083(14) 0.93203(11) 0.0546(3) Uani d . 1 O
O4 -0.05790(19) 1.00945(16) 0.82345(12) 0.0623(4) Uani d D 1 O
H4A -0.071(3) 1.045(3) 0.9062(13) 0.093 Uiso d D 1 H
O5 -0.20053(14) 0.83024(15) 0.56072(11) 0.0512(3) Uani d . 1 O
O6 0.24990(14) 0.55808(15) 0.32166(10) 0.0505(3) Uani d . 1 O
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 120.35(12)
C6 C1 C7 116.69(12)
C2 C1 C7 122.77(12)
C3 C2 C1 117.97(12)
C3 C2 C9 122.14(12)
C1 C2 C9 119.88(12)
O5 C3 C4 121.37(12)
O5 C3 C2 117.53(11)
C4 C3 C2 121.07(12)
C5 C4 C3 119.49(12)
C5 C4 H4 120.3
C3 C4 H4 120.3
O6 C5 C4 123.65(12)
O6 C5 C6 115.93(11)
C4 C5 C6 120.42(12)
C1 C6 C5 120.66(12)
C1 C6 H6 119.7
C5 C6 H6 119.7
C8 C7 C1 114.89(11)
C8 C7 H7A 108.5
C1 C7 H7A 108.5
C8 C7 H7B 108.5
C1 C7 H7B 108.5
H7A C7 H7B 107.5
O2 C8 O1 122.97(13)
O2 C8 C7 124.33(12)
O1 C8 C7 112.59(12)
O3 C9 O4 121.67(12)
O3 C9 C2 121.09(12)
O4 C9 C2 117.24(12)
O5 C10 H10A 109.5
O5 C10 H10B 109.5
H10A C10 H10B 109.5
O5 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O6 C11 H11A 109.5
O6 C11 H11B 109.5
H11A C11 H11B 109.5
O6 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C8 O1 H1 108.8(16)
C9 O4 H4A 107.1(16)
C3 O5 C10 117.93(11)
C5 O6 C11 117.71(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3743(19)
C1 C2 1.4128(18)
C1 C7 1.5131(18)
C2 C3 1.4085(18)
C2 C9 1.4822(18)
C3 O5 1.3552(15)
C3 C4 1.3896(18)
C4 C5 1.3814(18)
C4 H4 0.9300
C5 O6 1.3625(16)
C5 C6 1.3888(19)
C6 H6 0.9300
C7 C8 1.490(2)
C7 H7A 0.9700
C7 H7B 0.9700
C8 O2 1.2136(17)
C8 O1 1.3177(16)
C9 O3 1.2346(17)
C9 O4 1.2979(17)
C10 O5 1.4197(17)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 O6 1.4243(18)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
O1 H1 0.853(10)
O4 H4A 0.850(10)
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
C7 H7B O3 . 0.97 2.43 2.7829(19) 101
C10 H10C O2 2_566 0.96 2.56 3.4144(19) 148
O4 H4A O3 2_577 0.850(10) 1.821(11) 2.6606(14) 169(2)
O1 H1 O2 2_667 0.853(10) 1.801(10) 2.6532(14) 178(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
C6 C1 C2 C3 -1.54(19)
C7 C1 C2 C3 173.28(12)
C6 C1 C2 C9 177.77(12)
C7 C1 C2 C9 -7.40(19)
C1 C2 C3 O5 179.67(11)
C9 C2 C3 O5 0.37(19)
C1 C2 C3 C4 1.48(19)
C9 C2 C3 C4 -177.82(12)
O5 C3 C4 C5 -178.56(12)
C2 C3 C4 C5 -0.4(2)
C3 C4 C5 O6 -179.78(12)
C3 C4 C5 C6 -0.6(2)
C2 C1 C6 C5 0.6(2)
C7 C1 C6 C5 -174.55(11)
O6 C5 C6 C1 179.77(11)
C4 C5 C6 C1 0.5(2)
C6 C1 C7 C8 -97.26(15)
C2 C1 C7 C8 87.74(15)
C1 C7 C8 O2 15.7(2)
C1 C7 C8 O1 -167.93(11)
C3 C2 C9 O3 149.68(14)
C1 C2 C9 O3 -29.6(2)
C3 C2 C9 O4 -31.08(19)
C1 C2 C9 O4 149.64(13)
C4 C3 O5 C10 -12.8(2)
C2 C3 O5 C10 168.99(12)
C4 C5 O6 C11 11.6(2)
C6 C5 O6 C11 -167.67(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3378231
