#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/95/2239596.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_2239596
loop_
_publ_author_name
'Karthikeyan, S.'
'Sethusankar, K.'
'Selvakumar, R.'
'Bakthadoss, M.'
_publ_section_title
;
 Methyl (E)-3-(2-formylphenoxy)acrylate
;
_journal_coeditor_code           SU2732
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o709
_journal_paper_doi               10.1107/S1600536814010617
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H10 O4'
_chemical_formula_moiety         'C11 H10 O4'
_chemical_formula_sum            'C11 H10 O4'
_chemical_formula_weight         206.19
_chemical_name_systematic
;
Methyl (E)-3-(2-formylphenoxy)acrylate
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.868(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.7458(8)
_cell_length_b                   4.0629(2)
_cell_length_c                   14.5745(7)
_cell_measurement_reflns_used    2015
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      1.21
_cell_volume                     1000.13(8)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       '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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13052
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0446
_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)+(0.1001P)²+0.0957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1546
_reflns_number_gt                1523
_reflns_number_total             2015
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2732sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239596
_cod_database_fobs_code          2239596
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_symmetry_multiplicity
C C1 0.19462(11) 0.6483(5) 1.09554(11) 0.0570(5) Uani d . 1 1
H H1 0.2426 0.7588 1.1079 0.068 Uiso calc R 1 1
C C2 0.16126(8) 0.4928(4) 1.00055(10) 0.0437(4) Uani d . 1 1
C C3 0.08802(9) 0.3378(4) 0.97865(12) 0.0518(5) Uani d . 1 1
H H3 0.0621 0.3250 1.0252 0.062 Uiso calc R 1 1
C C4 0.05341(10) 0.2034(5) 0.88901(13) 0.0574(5) Uani d . 1 1
H H4 0.0040 0.1033 0.8746 0.069 Uiso calc R 1 1
C C5 0.09250(10) 0.2182(5) 0.82056(12) 0.0545(5) Uani d . 1 1
H H5 0.0692 0.1265 0.7600 0.065 Uiso calc R 1 1
C C6 0.16554(9) 0.3671(4) 0.84083(11) 0.0484(4) Uani d . 1 1
H H6 0.1918 0.3734 0.7946 0.058 Uiso calc R 1 1
C C7 0.19943(8) 0.5068(4) 0.93033(10) 0.0425(4) Uani d . 1 1
C C8 0.30241(9) 0.7868(4) 0.88985(11) 0.0463(4) Uani d . 1 1
H H8 0.2706 0.8014 0.8260 0.056 Uiso calc R 1 1
C C9 0.37579(9) 0.8937(5) 0.91462(12) 0.0542(5) Uani d . 1 1
H H9 0.4075 0.8649 0.9780 0.065 Uiso calc R 1 1
C C10 0.40974(9) 1.0549(5) 0.84737(12) 0.0516(4) Uani d . 1 1
C C11 0.39059(12) 1.2299(6) 0.68764(14) 0.0655(5) Uani d . 1 1
H H11A 0.4103 1.4452 0.7097 0.098 Uiso calc R 1 1
H H11B 0.3494 1.2484 0.6272 0.098 Uiso calc R 1 1
H H11C 0.4329 1.0976 0.6794 0.098 Uiso calc R 1 1
O O1 0.35946(7) 1.0781(3) 0.75754(8) 0.0598(4) Uani d . 1 1
O O2 0.47632(7) 1.1596(4) 0.86851(10) 0.0723(5) Uani d . 1 1
O O3 0.27287(6) 0.6544(3) 0.95771(7) 0.0541(4) Uani d . 1 1
O O4 0.16367(9) 0.6413(5) 1.15808(9) 0.0821(5) Uani d . 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
C1 0.0536(10) 0.0738(13) 0.0448(8) 0.0075(8) 0.0171(7) 0.0039(8)
C2 0.0403(8) 0.0498(10) 0.0419(8) 0.0095(6) 0.0142(6) 0.0084(7)
C3 0.0432(9) 0.0604(11) 0.0562(9) 0.0071(7) 0.0220(7) 0.0119(8)
C4 0.0442(9) 0.0590(11) 0.0665(11) -0.0046(8) 0.0134(8) 0.0077(8)
C5 0.0531(10) 0.0542(10) 0.0504(9) 0.0009(8) 0.0074(7) 0.0007(8)
C6 0.0485(9) 0.0547(10) 0.0443(8) 0.0048(7) 0.0175(7) 0.0049(7)
C7 0.0357(7) 0.0485(10) 0.0429(7) 0.0054(6) 0.0115(6) 0.0082(6)
C8 0.0411(8) 0.0565(10) 0.0435(8) 0.0025(7) 0.0162(6) 0.0013(7)
C9 0.0425(8) 0.0710(12) 0.0490(9) -0.0019(8) 0.0137(7) -0.0027(8)
C10 0.0383(8) 0.0609(11) 0.0580(9) -0.0018(7) 0.0184(7) -0.0063(8)
C11 0.0639(11) 0.0721(13) 0.0669(11) -0.0039(10) 0.0297(9) 0.0095(10)
O1 0.0487(7) 0.0767(9) 0.0553(7) -0.0123(6) 0.0181(5) 0.0033(6)
O2 0.0431(7) 0.1021(13) 0.0731(8) -0.0180(7) 0.0197(6) -0.0050(7)
O3 0.0403(6) 0.0800(9) 0.0427(6) -0.0071(5) 0.0139(5) 0.0042(5)
O4 0.0787(10) 0.1250(15) 0.0509(7) -0.0008(9) 0.0322(7) -0.0084(7)
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
O4 C1 C2 123.98(17)
O4 C1 H1 118.0
C2 C1 H1 118.0
C3 C2 C7 118.80(14)
C3 C2 C1 119.24(14)
C7 C2 C1 121.91(15)
C4 C3 C2 120.77(15)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 119.52(16)
C3 C4 H4 120.2
C5 C4 H4 120.2
C6 C5 C4 120.83(15)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C7 119.46(15)
C5 C6 H6 120.3
C7 C6 H6 120.3
O3 C7 C6 123.51(13)
O3 C7 C2 115.83(13)
C6 C7 C2 120.61(14)
C9 C8 O3 120.00(14)
C9 C8 H8 120.0
O3 C8 H8 120.0
C8 C9 C10 122.98(15)
C8 C9 H9 118.5
C10 C9 H9 118.5
O2 C10 O1 122.10(15)
O2 C10 C9 124.32(16)
O1 C10 C9 113.58(14)
O1 C11 H11A 109.5
O1 C11 H11B 109.5
H11A C11 H11B 109.5
O1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 O1 C11 115.85(13)
C8 O3 C7 120.10(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O4 1.200(2)
C1 C2 1.471(2)
C1 H1 0.9300
C2 C3 1.390(2)
C2 C7 1.3910(19)
C3 C4 1.375(3)
C3 H3 0.9300
C4 C5 1.380(2)
C4 H4 0.9300
C5 C6 1.378(2)
C5 H5 0.9300
C6 C7 1.380(2)
C6 H6 0.9300
C7 O3 1.3778(18)
C8 C9 1.314(2)
C8 O3 1.3640(18)
C8 H8 0.9300
C9 C10 1.454(2)
C9 H9 0.9300
C10 O2 1.2035(19)
C10 O1 1.342(2)
C11 O1 1.438(2)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 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
C9 H9 O2 3_677.01 0.93 2.54 3.440(2) 164
C8 H8 O4 4_575 0.93 2.61 3.529(2) 171.2
C11 H11C O2 2_646 0.96 2.63 3.578(2) 167.6
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
O4 C1 C2 C3 2.7(3)
O4 C1 C2 C7 -179.85(17)
C7 C2 C3 C4 -0.6(2)
C1 C2 C3 C4 176.94(17)
C2 C3 C4 C5 1.0(3)
C3 C4 C5 C6 -0.3(3)
C4 C5 C6 C7 -0.9(3)
C5 C6 C7 O3 178.55(15)
C5 C6 C7 C2 1.3(2)
C3 C2 C7 O3 -178.02(14)
C1 C2 C7 O3 4.5(2)
C3 C2 C7 C6 -0.5(2)
C1 C2 C7 C6 -178.03(15)
O3 C8 C9 C10 -176.28(16)
C8 C9 C10 O2 178.78(19)
C8 C9 C10 O1 -1.2(3)
O2 C10 O1 C11 1.2(3)
C9 C10 O1 C11 -178.82(16)
C9 C8 O3 C7 -172.25(16)
C6 C7 O3 C8 26.2(2)
C2 C7 O3 C8 -156.37(14)
