#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/95/2239506.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_2239506
loop_
_publ_author_name
'Lundvall, Fredrik'
'Wragg, David Stephen'
'Dietzel, Pascal D. C.'
'Fjellvåg, Helmer'
_publ_section_title
;
 4,4'-Dimethoxybiphenyl-3,3'-dicarboxylic acid
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o615
_journal_paper_doi               10.1107/S1600536814008599
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C16 H14 O6'
_chemical_formula_moiety         'C16 H14 O6'
_chemical_formula_sum            'C16 H14 O6'
_chemical_formula_weight         302.27
_chemical_name_systematic
;
4,4'-Dimethoxybiphenyl-3,3'-dicarboxylic acid
;
_space_group_IT_number           72
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-I 2 2c'
_symmetry_space_group_name_H-M   'I b a m'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.138(2)
_cell_length_b                   15.615(3)
_cell_length_c                   6.7726(11)
_cell_measurement_reflns_used    2142
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.61
_cell_volume                     1389.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2004) and ChemBioDraw Ultra (CambridgeSoft,
2009)
;
_computing_publication_material
'publCIF (Westrip, 2010) and WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5188
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0462
_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)+(0.0765P)²+0.4964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                689
_reflns_number_total             779
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            qm2105sup1.cif
_cod_data_source_block           I
_cod_database_code               2239506
_cod_database_fobs_code          2239506
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, -z+1/2'
'x+1, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x, -y, z+1/2'
'-x, y, 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
C C1 0.44707(14) 0.48358(10) 0.0000 0.0371(5) Uani d S 1 2
C C2 0.36404(15) 0.53875(11) 0.0000 0.0386(5) Uani d S 1 2
H H2 0.3761 0.5974 0.0000 0.046 Uiso calc SR 1 2
C C3 0.26411(14) 0.51030(12) 0.0000 0.0396(5) Uani d S 1 2
C C4 0.24524(16) 0.42222(12) 0.0000 0.0428(5) Uani d S 1 2
C C5 0.32608(16) 0.36538(12) 0.0000 0.0478(6) Uani d S 1 2
H H5 0.3141 0.3067 0.0000 0.057 Uiso calc SR 1 2
C C6 0.42446(16) 0.39603(12) 0.0000 0.0457(6) Uani d S 1 2
H H6 0.4779 0.3570 0.0000 0.055 Uiso calc SR 1 2
C C7 0.18295(17) 0.57787(13) 0.0000 0.0492(6) Uani d S 1 2
C C8 0.1198(2) 0.30898(14) 0.0000 0.0694(8) Uani d S 1 2
H H8A 0.0471 0.3030 0.0000 0.104 Uiso calc SR 1 2
H H8B 0.1474 0.2821 0.1157 0.104 Uiso calc PR 0.50 1
H H8C 0.1474 0.2821 -0.1157 0.104 Uiso calc PR 0.50 1
O O1 0.08706(12) 0.55256(10) 0.0000 0.0868(8) Uani d S 1 2
H H1 0.0839 0.5026 -0.0370 0.130 Uiso calc PR 0.50 1
O O2 0.20123(13) 0.65265(9) 0.0000 0.0658(6) Uani d S 1 2
O O3 0.14575(12) 0.39725(9) 0.0000 0.0629(6) Uani d S 1 2
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
C1 0.0400(11) 0.0292(10) 0.0422(10) -0.0009(7) 0.000 0.000
C2 0.0414(11) 0.0260(8) 0.0484(11) -0.0003(7) 0.000 0.000
C3 0.0390(10) 0.0284(10) 0.0515(11) 0.0009(8) 0.000 0.000
C4 0.0365(11) 0.0331(10) 0.0586(12) -0.0037(7) 0.000 0.000
C5 0.0461(12) 0.0253(9) 0.0718(15) -0.0020(8) 0.000 0.000
C6 0.0415(11) 0.0281(10) 0.0675(14) 0.0039(8) 0.000 0.000
C7 0.0403(12) 0.0308(10) 0.0765(15) 0.0016(8) 0.000 0.000
C8 0.0497(13) 0.0349(11) 0.124(2) -0.0119(10) 0.000 0.000
O1 0.0360(9) 0.0414(9) 0.183(2) 0.0040(7) 0.000 0.000
O2 0.0488(9) 0.0284(8) 0.1201(16) 0.0036(6) 0.000 0.000
O3 0.0399(9) 0.0307(8) 0.1181(15) -0.0046(6) 0.000 0.000
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C6 . 116.04(18)
C2 C1 C1 9_665 121.45(19)
C6 C1 C1 9_665 122.5(2)
C3 C2 C1 . 123.00(17)
C3 C2 H2 . 118.5
C1 C2 H2 . 118.5
C2 C3 C4 . 118.92(18)
C2 C3 C7 . 116.61(17)
C4 C3 C7 . 124.48(18)
O3 C4 C5 . 123.50(18)
O3 C4 C3 . 116.84(18)
C5 C4 C3 . 119.67(19)
C6 C5 C4 . 119.79(17)
C6 C5 H5 . 120.1
C4 C5 H5 . 120.1
C5 C6 C1 . 122.59(18)
C5 C6 H6 . 118.7
C1 C6 H6 . 118.7
O2 C7 O1 . 119.04(19)
O2 C7 C3 . 123.1(2)
O1 C7 C3 . 117.88(17)
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
C7 O1 H1 . 109.5
C4 O3 C8 . 120.52(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.390(3)
C1 C6 . 1.399(2)
C1 C1 9_665 1.482(4)
C2 C3 . 1.386(3)
C2 H2 . 0.9300
C3 C4 . 1.398(3)
C3 C7 . 1.500(3)
C4 O3 . 1.364(3)
C4 C5 . 1.384(3)
C5 C6 . 1.378(3)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 O2 . 1.192(2)
C7 O1 . 1.320(3)
C8 O3 . 1.420(2)
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
O1 H1 . 0.8200
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
O1 H1 O3 . 0.82 1.85 2.545(2) 141.3
O1 H1 O1 2_565 0.82 2.42 2.816(3) 110.8
C5 H5 O2 3_545 0.93 2.41 3.341(2) 175
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
C6 C1 C2 C3 . 0.0
C1 C1 C2 C3 9_665 180.0
C1 C2 C3 C4 . 0.0
C1 C2 C3 C7 . 180.0
C2 C3 C4 O3 . 180.0
C7 C3 C4 O3 . 0.0
C2 C3 C4 C5 . 0.0
C7 C3 C4 C5 . 180.0
O3 C4 C5 C6 . 180.0
C3 C4 C5 C6 . 0.0
C4 C5 C6 C1 . 0.0
C2 C1 C6 C5 . 0.0
C1 C1 C6 C5 9_665 180.0
C2 C3 C7 O2 . 0.0
C4 C3 C7 O2 . 180.0
C2 C3 C7 O1 . 180.0
C4 C3 C7 O1 . 0.0
C5 C4 O3 C8 . 0.0
C3 C4 O3 C8 . 180.0
