#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/81/2228167.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_2228167
loop_
_publ_author_name
'Collas, Alain'
'Vande Velde, Christophe M. L.'
'Blockhuys, Frank'
_publ_section_title
;
 3-(2-Formylphenoxy)propanoic acid
;
_journal_coeditor_code           ZL2308
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2662
_journal_paper_doi               10.1107/S1600536810038079
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H10 O4'
_chemical_formula_moiety         'C10 H10 O4'
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.18
_chemical_melting_point          381
_chemical_name_common            '3-(o-formylphenoxy) propanoic acid'
_chemical_name_systematic
;
3-(2-formylphenoxy)propanoic acid
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   15.269(4)
_cell_length_b                   7.167(2)
_cell_length_c                   17.136(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.98
_cell_measurement_theta_min      6.16
_cell_volume                     1875.2(9)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)'
_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 CAD-4'
_diffrn_measurement_method       ' ω/2θ 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  0.000
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1718
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ' Block'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0467
_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)+(0.0516P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                964
_reflns_number_total             1718
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2308.cif
_cod_data_source_block           I
_cod_database_code               2228167
_cod_database_fobs_code          2228167
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
H H21a 0.0220(14) 0.495(4) 0.3039(14) 0.049(7) Uiso d . 1 . .
H H22b -0.1019(16) 0.478(4) 0.2296(16) 0.063(9) Uiso d . 1 . .
H H22a -0.1276(16) 0.540(4) 0.3140(14) 0.058(9) Uiso d . 1 . .
H H21b 0.0046(17) 0.281(4) 0.2824(15) 0.058(8) Uiso d . 1 . .
H H5 0.2323(19) 0.109(4) 0.5447(16) 0.073(10) Uiso d . 1 . .
H H3 0.1355(15) 0.315(4) 0.3435(14) 0.049(8) Uiso d . 1 . .
H H41 -0.1930(19) 0.040(6) 0.2804(19) 0.104(13) Uiso d . 1 . .
H H4 0.2503(19) 0.196(4) 0.4169(15) 0.058(9) Uiso d . 1 . .
H H6 0.092(2) 0.133(4) 0.6011(18) 0.081(11) Uiso d . 1 . .
H H1 -0.100(2) 0.276(4) 0.5065(19) 0.099(12) Uiso d . 1 . .
O O3 -0.14623(11) 0.1255(3) 0.28392(12) 0.0509(6) Uani d . 1 . .
O O2 -0.02664(10) 0.3422(3) 0.39246(10) 0.0464(5) Uani d . 1 . .
O O4 -0.25446(11) 0.3279(2) 0.28021(11) 0.0562(6) Uani d . 1 . .
C C23 -0.17679(16) 0.2958(3) 0.28326(14) 0.0384(6) Uani d . 1 . .
C C2 0.04663(17) 0.2827(3) 0.43064(16) 0.0414(7) Uani d . 1 . .
C C1 0.03508(17) 0.2307(4) 0.50805(16) 0.0443(7) Uani d . 1 . .
C C21 -0.01910(17) 0.3884(4) 0.31172(16) 0.0426(7) Uani d . 1 . .
O O1 -0.06445(15) 0.2082(3) 0.61361(12) 0.0779(7) Uani d . 1 . .
C C22 -0.10849(17) 0.4449(4) 0.28378(19) 0.0421(7) Uani d . 1 . .
C C3 0.12868(17) 0.2735(4) 0.39650(18) 0.0511(8) Uani d . 1 . .
C C6 0.1071(2) 0.1672(5) 0.5502(2) 0.0625(9) Uani d . 1 . .
C C11 -0.0514(2) 0.2416(4) 0.54553(18) 0.0565(8) Uani d . 1 . .
C C4 0.1983(2) 0.2109(5) 0.4398(2) 0.0690(10) Uani d . 1 . .
C C5 0.1876(2) 0.1563(6) 0.5161(2) 0.0761(11) Uani d . 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
C23 O3 H41 . . 110(2) ?
C2 O2 C21 . . 118.1(2) ?
O4 C23 O3 . . 121.9(2) ?
O4 C23 C22 . . 123.3(2) ?
O3 C23 C22 . . 114.8(2) ?
O2 C2 C3 . . 123.7(3) ?
O2 C2 C1 . . 116.0(2) ?
C3 C2 C1 . . 120.4(3) ?
C6 C1 C2 . . 118.9(3) ?
C6 C1 C11 . . 120.0(3) ?
C2 C1 C11 . . 121.1(3) ?
O2 C21 C22 . . 107.3(2) ?
O2 C21 H21a . . 111.0(14) ?
C22 C21 H21a . . 108.9(14) ?
O2 C21 H21b . . 110.0(16) ?
C22 C21 H21b . . 112.4(15) ?
H21a C21 H21b . . 107(2) ?
C23 C22 C21 . . 116.3(2) ?
C23 C22 H22b . . 104.2(16) ?
C21 C22 H22b . . 106.2(15) ?
C23 C22 H22a . . 108.5(17) ?
C21 C22 H22a . . 108.3(17) ?
H22b C22 H22a . . 113(2) ?
C4 C3 C2 . . 119.2(3) ?
C4 C3 H3 . . 121.8(14) ?
C2 C3 H3 . . 118.9(15) ?
C5 C6 C1 . . 120.6(4) ?
C5 C6 H6 . . 127(2) ?
C1 C6 H6 . . 112.3(19) ?
O1 C11 C1 . . 124.0(3) ?
O1 C11 H1 . . 123.9(19) ?
C1 C11 H1 . . 112.0(19) ?
C3 C4 C5 . . 121.0(3) ?
C3 C4 H4 . . 119.5(18) ?
C5 C4 H4 . . 119.2(18) ?
C6 C5 C4 . . 119.9(4) ?
C6 C5 H5 . . 118.0(19) ?
C4 C5 H5 . . 122.1(19) ?
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
O3 C23 . 1.306(3) ?
O3 H41 . 0.95(4) ?
O2 C2 . 1.364(3) ?
O2 C21 . 1.427(3) ?
O4 C23 . 1.209(3) ?
C23 C22 . 1.493(3) ?
C2 C3 . 1.384(4) ?
C2 C1 . 1.389(4) ?
C1 C6 . 1.392(4) ?
C1 C11 . 1.471(4) ?
C21 C22 . 1.502(4) ?
C21 H21a . 1.00(3) ?
C21 H21b . 0.99(3) ?
O1 C11 . 1.208(3) ?
C22 H22b . 0.96(3) ?
C22 H22a . 0.90(3) ?
C3 C4 . 1.371(4) ?
C3 H3 . 0.96(2) ?
C6 C5 . 1.363(5) ?
C6 H6 . 0.93(3) ?
C11 H1 . 1.03(3) ?
C4 C5 . 1.375(5) ?
C4 H4 . 0.89(3) ?
C5 H5 . 0.91(3) ?
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
_geom_hbond_publ_flag
C6 H6 O1 . 0.94(3) 2.46(3) 2.851(4) 105(2) n
C11 H1 O2 . 1.03(3) 2.30(3) 2.746(4) 105(2) n
O3 H41 O4 7 0.94(4) 1.72(4) 2.618(3) 158(3) y
C21 H21a O1 5_566 1.00(3) 2.64(3) 3.409(4) 134.5(2) y
C22 H22b O1 8_565 0.96(3) 2.46(3) 3.187(4) 132(2) y
C21 H21a O3 4 1.00(3) 2.60(2) 3.456(3) 144(2) y
C3 H3 O4 6_656 0.96(2) 2.71(2) 3.536(4) 144.9(2) y
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
C21 O2 C2 C3 . . . . 3.4(4) ?
C21 O2 C2 C1 . . . . -176.9(2) ?
O2 C2 C1 C6 . . . . 179.5(2) ?
C3 C2 C1 C6 . . . . -0.8(4) ?
O2 C2 C1 C11 . . . . -0.4(4) ?
C3 C2 C1 C11 . . . . 179.3(3) ?
C2 O2 C21 C22 . . . . 178.8(2) ?
O4 C23 C22 C21 . . . . 162.1(3) ?
O3 C23 C22 C21 . . . . -20.0(4) ?
O2 C21 C22 C23 . . . . -65.9(3) ?
O2 C2 C3 C4 . . . . -179.7(3) ?
C1 C2 C3 C4 . . . . 0.6(4) ?
C2 C1 C6 C5 . . . . 0.0(4) ?
C11 C1 C6 C5 . . . . 179.9(3) ?
C6 C1 C11 O1 . . . . 4.3(4) ?
C2 C1 C11 O1 . . . . -175.8(3) ?
C2 C3 C4 C5 . . . . 0.4(5) ?
C1 C6 C5 C4 . . . . 1.0(5) ?
C3 C4 C5 C6 . . . . -1.2(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14852188
