#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/81/2228173.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_2228173
loop_
_publ_author_name
'Collas, Alain'
'Vande Velde, Christophe M. L.'
'Blockhuys, Frank'
_publ_section_title
;
 2-(4-Formyl-2,6-dimethoxyphenoxy)acetic acid
;
_journal_coeditor_code           ZL2319
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3003
_journal_paper_doi               10.1107/S1600536810043990
_journal_volume                  66
_journal_year                    2010
_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          415
_chemical_name_common            '4-(acetic acid)-syringaldehyde'
_chemical_name_systematic
;
2-(4-Formyl-2,6-dimethoxyphenoxy)acetic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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
_cell_angle_beta                 113.67(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.350(2)
_cell_length_b                   7.4160(10)
_cell_length_c                   17.374(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.21
_cell_measurement_theta_min      8.96
_cell_volume                     1103.4(6)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius MACH3'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4025
_diffrn_reflns_theta_full        25.32
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.150
_refine_ls_extinction_coef       0.0086(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2015
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0358
_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)+(0.0427P)²+0.1341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                1292
_reflns_number_total             2015
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2319.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228173
_cod_database_fobs_code          2228173
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_disorder_assembly
_atom_site_disorder_group
O O11A 0.8177(2) 0.6876(3) 0.52772(13) 0.0677(9) Uani d PDU 0.785(6) A 1
C C11A 0.6811(5) 0.6988(12) 0.5115(3) 0.0490(13) Uani d PD 0.785(6) A 1
H H11A 0.6121 0.6482 0.4613 0.059 Uiso calc PR 0.785(6) A 1
C C11B 0.720(3) 0.712(5) 0.5283(16) 0.0490(13) Uani d PD 0.215(6) A 2
H H11B 0.8278 0.7181 0.5571 0.059 Uiso calc PR 0.215(6) A 2
O O11B 0.6629(10) 0.6437(14) 0.4603(6) 0.078(3) Uani d PDU 0.215(6) A 2
O O4 0.39907(13) 1.04247(17) 0.70196(7) 0.0376(3) Uani d . 1 . .
O O5 0.22382(14) 0.89227(19) 0.55872(8) 0.0449(4) Uani d . 1 . .
O O3 0.71034(14) 1.0208(2) 0.76755(8) 0.0478(4) Uani d . 1 A .
C C6 0.4523(2) 0.7946(3) 0.53433(11) 0.0388(5) Uani d . 1 A .
H H6 0.3923 0.7439 0.4824 0.047 Uiso calc R 1 . .
C C2 0.7062(2) 0.8612(3) 0.64352(11) 0.0414(5) Uani d . 1 A .
H H2 0.8144 0.8545 0.6638 0.050 Uiso calc R 1 . .
C C5 0.38175(19) 0.8774(2) 0.58135(10) 0.0345(4) Uani d . 1 . .
O O42 0.13206(15) 0.9328(2) 0.70058(9) 0.0604(5) Uani d . 1 . .
H H42 0.1655 0.9578 0.6649 0.091 Uiso calc R 1 . .
C C4 0.47318(19) 0.9529(2) 0.65853(10) 0.0334(4) Uani d . 1 A .
O O41 0.22968(17) 0.8754(2) 0.83608(9) 0.0623(5) Uani d . 1 . .
C C1 0.6143(2) 0.7884(3) 0.56601(11) 0.0392(5) Uani d D 1 . .
C C41 0.4098(2) 0.9607(3) 0.77859(11) 0.0380(4) Uani d . 1 . .
H H41A 0.4634 1.0416 0.8252 0.046 Uiso calc R 1 . .
H H41B 0.4701 0.8502 0.7880 0.046 Uiso calc R 1 . .
C C3 0.6358(2) 0.9442(2) 0.69064(11) 0.0369(4) Uani d . 1 . .
C C42 0.2502(2) 0.9191(3) 0.77494(12) 0.0429(5) Uani d . 1 . .
C C51 0.1233(2) 0.8060(3) 0.48261(12) 0.0551(6) Uani d . 1 . .
H H51A 0.1374 0.8599 0.4359 0.083 Uiso calc R 1 . .
H H51B 0.0167 0.8202 0.4755 0.083 Uiso calc R 1 . .
H H51C 0.1484 0.6800 0.4853 0.083 Uiso calc R 1 . .
C C31 0.8750(3) 0.9877(4) 0.80939(15) 0.0730(7) Uani d . 1 . .
H H31A 0.8941 0.8602 0.8120 0.110 Uiso calc R 1 A .
H H31B 0.9128 1.0359 0.8653 0.110 Uiso calc R 1 . .
H H31C 0.9282 1.0449 0.7788 0.110 Uiso calc R 1 . .
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O11A C11A C1 . . 124.3(3) ?
O11A C11A H11A . . 117.8 ?
C1 C11A H11A . . 117.8 ?
O11B C11B C1 . . 118.8(19) ?
O11B C11B H11B . . 120.6 ?
C1 C11B H11B . . 120.6 ?
C4 O4 C41 . . 116.19(13) ?
C5 O5 C51 . . 117.50(14) ?
C3 O3 C31 . . 116.68(16) ?
C5 C6 C1 . . 118.91(17) ?
C5 C6 H6 . . 120.5 ?
C1 C6 H6 . . 120.5 ?
C3 C2 C1 . . 119.53(17) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
O5 C5 C6 . . 125.46(16) ?
O5 C5 C4 . . 114.83(15) ?
C6 C5 C4 . . 119.71(15) ?
C42 O42 H42 . . 109.5 ?
O4 C4 C5 . . 118.19(15) ?
O4 C4 C3 . . 120.58(16) ?
C5 C4 C3 . . 121.20(16) ?
C2 C1 C6 . . 121.65(17) ?
C2 C1 C11A . . 122.7(2) ?
C6 C1 C11A . . 115.7(2) ?
C2 C1 C11B . . 108.2(9) ?
C6 C1 C11B . . 130.1(9) ?
O4 C41 C42 . . 110.56(15) ?
O4 C41 H41A . . 109.5 ?
C42 C41 H41A . . 109.5 ?
O4 C41 H41B . . 109.5 ?
C42 C41 H41B . . 109.5 ?
H41A C41 H41B . . 108.1 ?
O3 C3 C2 . . 126.16(16) ?
O3 C3 C4 . . 114.84(16) ?
C2 C3 C4 . . 119.00(16) ?
O41 C42 O42 . . 121.25(19) ?
O41 C42 C41 . . 121.93(18) ?
O42 C42 C41 . . 116.83(16) ?
O5 C51 H51A . . 109.5 ?
O5 C51 H51B . . 109.5 ?
H51A C51 H51B . . 109.5 ?
O5 C51 H51C . . 109.5 ?
H51A C51 H51C . . 109.5 ?
H51B C51 H51C . . 109.5 ?
O3 C31 H31A . . 109.5 ?
O3 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
O3 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11A C11A . 1.195(5) ?
C11A C1 . 1.485(4) ?
C11A H11A . 0.9300 ?
C11B O11B . 1.196(17) ?
C11B C1 . 1.498(16) ?
C11B H11B . 0.9300 ?
O4 C4 . 1.382(2) ?
O4 C41 . 1.430(2) ?
O5 C5 . 1.371(2) ?
O5 C51 . 1.430(2) ?
O3 C3 . 1.359(2) ?
O3 C31 . 1.435(3) ?
C6 C5 . 1.383(2) ?
C6 C1 . 1.389(3) ?
C6 H6 . 0.9300 ?
C2 C3 . 1.383(3) ?
C2 C1 . 1.384(3) ?
C2 H2 . 0.9300 ?
C5 C4 . 1.386(2) ?
O42 C42 . 1.324(2) ?
O42 H42 . 0.8200 ?
C4 C3 . 1.395(2) ?
O41 C42 . 1.197(2) ?
C41 C42 . 1.500(3) ?
C41 H41A . 0.9700 ?
C41 H41B . 0.9700 ?
C51 H51A . 0.9600 ?
C51 H51B . 0.9600 ?
C51 H51C . 0.9600 ?
C31 H31A . 0.9600 ?
C31 H31B . 0.9600 ?
C31 H31C . 0.9600 ?
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
O42 H42 O4 . 0.82 2.11 2.617(2) 120
O42 H42 O5 . 0.82 2.18 2.932(2) 153
C6 H6 O41 4_564 0.93 2.54 3.468(3) 176
C41 H41A O11B 4_565 0.97 2.71 3.189(9) 111
C51 H51B O11A 1_455 0.96 2.57 3.369(3) 141
C31 H31B O11A 2_756 0.96 2.70 3.454(3) 136
C41 H41B O4 2_646 0.97 2.56 3.527(3) 173
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C51 O5 C5 C6 . . . . 3.9(3) ?
C51 O5 C5 C4 . . . . -175.66(17) ?
C1 C6 C5 O5 . . . . -179.30(17) ?
C1 C6 C5 C4 . . . . 0.2(3) ?
C41 O4 C4 C5 . . . . 112.81(18) ?
C41 O4 C4 C3 . . . . -69.2(2) ?
O5 C5 C4 O4 . . . . -3.6(2) ?
C6 C5 C4 O4 . . . . 176.83(16) ?
O5 C5 C4 C3 . . . . 178.46(16) ?
C6 C5 C4 C3 . . . . -1.1(3) ?
C3 C2 C1 C6 . . . . -0.7(3) ?
C3 C2 C1 C11A . . . . 179.4(5) ?
C3 C2 C1 C11B . . . . 178.6(17) ?
C5 C6 C1 C2 . . . . 0.6(3) ?
C5 C6 C1 C11A . . . . -179.4(4) ?
C5 C6 C1 C11B . . . . -178(2) ?
O11A C11A C1 C2 . . . . -2.9(10) ?
O11A C11A C1 C6 . . . . 177.2(6) ?
O11A C11A C1 C11B . . . . 0(7) ?
O11B C11B C1 C2 . . . . -179(3) ?
O11B C11B C1 C6 . . . . 0(4) ?
O11B C11B C1 C11A . . . . 3(4) ?
C4 O4 C41 C42 . . . . -120.89(17) ?
C31 O3 C3 C2 . . . . -10.5(3) ?
C31 O3 C3 C4 . . . . 169.40(19) ?
C1 C2 C3 O3 . . . . 179.70(17) ?
C1 C2 C3 C4 . . . . -0.2(3) ?
O4 C4 C3 O3 . . . . 3.3(2) ?
C5 C4 C3 O3 . . . . -178.83(17) ?
O4 C4 C3 C2 . . . . -176.79(17) ?
C5 C4 C3 C2 . . . . 1.1(3) ?
O4 C41 C42 O41 . . . . -168.63(19) ?
O4 C41 C42 O42 . . . . 11.4(2) ?
