#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/02/2230292.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_2230292
loop_
_publ_author_name
'Satyanarayana Reddy, J.'
'Ravi Kumar, N.'
'Venkata Prasad, J.'
'Gopikrishna, G.'
'Anand Solomon, K.'
_publ_section_title
;
 (Z)-2-(2-Hydroxy-4-methoxybenzylidene)-1-benzofuran-3(2H)-one
;
_journal_coeditor_code           DS2109
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1330
_journal_paper_doi               10.1107/S1600536811016217
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H12 O4'
_chemical_formula_moiety         'C16 H12 O4'
_chemical_formula_sum            'C16 H12 O4'
_chemical_formula_weight         268.26
_chemical_name_systematic
;
(Z)-2-(2-Hydroxy-4-methoxybenzylidene)-1-benzofuran-3(2H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.161(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1083(4)
_cell_length_b                   12.7072(7)
_cell_length_c                   14.4024(8)
_cell_measurement_reflns_used    3249
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.85
_cell_volume                     1280.52(12)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19357
_diffrn_reflns_theta_full        32.91
_diffrn_reflns_theta_max         32.91
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_correction_T_min  0.9057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.188
_refine_ls_extinction_coef       0.0043(16)
_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   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         4765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0683P)²+0.0121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                2533
_reflns_number_total             4765
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ds2109.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230292
_cod_database_fobs_code          2230292
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.33155(18) 0.81587(10) 0.10935(9) 0.0378(3) Uani d . 1 1 . .
C C2 0.3577(2) 0.79394(12) 0.20448(10) 0.0498(4) Uani d . 1 1 . .
H H2 0.3493 0.8460 0.2490 0.060 Uiso calc R 1 1 . .
C C3 0.3967(2) 0.69092(12) 0.22996(11) 0.0544(4) Uani d . 1 1 . .
H H3 0.4168 0.6732 0.2936 0.065 Uiso calc R 1 1 . .
C C4 0.4072(2) 0.61232(12) 0.16407(11) 0.0529(4) Uani d . 1 1 . .
H H4 0.4321 0.5433 0.1840 0.064 Uiso calc R 1 1 . .
C C5 0.3811(2) 0.63594(11) 0.06989(11) 0.0487(4) Uani d . 1 1 . .
H H5 0.3888 0.5838 0.0254 0.058 Uiso calc R 1 1 . .
C C6 0.34267(17) 0.73990(10) 0.04224(9) 0.0383(3) Uani d . 1 1 . .
C C7 0.31090(19) 0.79320(10) -0.04815(9) 0.0409(3) Uani d . 1 1 . .
C C8 0.27856(18) 0.90379(10) -0.02558(9) 0.0380(3) Uani d . 1 1 . .
C C9 0.24089(17) 0.98235(10) -0.08784(9) 0.0388(3) Uani d . 1 1 . .
H H9 0.2352 0.9621 -0.1503 0.047 Uiso calc R 1 1 . .
C C10 0.20767(16) 1.09256(10) -0.07510(9) 0.0362(3) Uani d . 1 1 . .
C C11 0.2172(2) 1.14095(10) 0.01304(10) 0.0440(3) Uani d . 1 1 . .
H H11 0.2418 1.0999 0.0673 0.053 Uiso calc R 1 1 . .
C C12 0.1913(2) 1.24709(11) 0.02151(10) 0.0492(4) Uani d . 1 1 . .
H H12 0.1987 1.2772 0.0809 0.059 Uiso calc R 1 1 . .
C C13 0.15384(19) 1.30956(10) -0.05866(10) 0.0412(3) Uani d . 1 1 . .
C C14 0.14158(17) 1.26536(10) -0.14673(9) 0.0389(3) Uani d . 1 1 . .
H H14 0.1155 1.3072 -0.2004 0.047 Uiso calc R 1 1 . .
C C15 0.16833(18) 1.15787(10) -0.15485(9) 0.0383(3) Uani d . 1 1 . .
C C16 0.0907(2) 1.48154(11) -0.12239(11) 0.0557(4) Uani d . 1 1 . .
H H16A 0.1933 1.4791 -0.1577 0.083 Uiso calc R 1 1 . .
H H16B 0.0756 1.5523 -0.1015 0.083 Uiso calc R 1 1 . .
H H16C -0.0256 1.4589 -0.1617 0.083 Uiso calc R 1 1 . .
O O1 0.29265(13) 0.91457(7) 0.07146(6) 0.0425(2) Uani d . 1 1 . .
O O2 0.30983(16) 0.75813(8) -0.12769(7) 0.0611(3) Uani d . 1 1 . .
O O3 0.15733(16) 1.11203(8) -0.24045(7) 0.0558(3) Uani d . 1 1 . .
O O4 0.13342(16) 1.41402(8) -0.04288(7) 0.0556(3) Uani d . 1 1 . .
H H3A 0.153(3) 1.1617(15) -0.2855(16) 0.092(7) Uiso d . 1 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
O1 C1 C6 . . 113.12(11) ?
O1 C1 C2 . . 124.11(12) ?
C6 C1 C2 . . 122.77(12) ?
C3 C2 C1 . . 116.33(14) ?
C3 C2 H2 . . 121.8 ?
C1 C2 H2 . . 121.8 ?
C2 C3 C4 . . 122.35(14) ?
C2 C3 H3 . . 118.8 ?
C4 C3 H3 . . 118.8 ?
C5 C4 C3 . . 120.32(14) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 118.46(14) ?
C4 C5 H5 . . 120.8 ?
C6 C5 H5 . . 120.8 ?
C1 C6 C5 . . 119.77(13) ?
C1 C6 C7 . . 106.47(11) ?
C5 C6 C7 . . 133.75(13) ?
O2 C7 C6 . . 130.00(13) ?
O2 C7 C8 . . 125.30(13) ?
C6 C7 C8 . . 104.70(11) ?
C9 C8 O1 . . 124.83(12) ?
C9 C8 C7 . . 125.89(12) ?
O1 C8 C7 . . 109.29(10) ?
C8 C9 C10 . . 131.29(12) ?
C8 C9 H9 . . 114.4 ?
C10 C9 H9 . . 114.4 ?
C11 C10 C15 . . 116.89(12) ?
C11 C10 C9 . . 124.08(12) ?
C15 C10 C9 . . 119.01(11) ?
C12 C11 C10 . . 121.80(13) ?
C12 C11 H11 . . 119.1 ?
C10 C11 H11 . . 119.1 ?
C11 C12 C13 . . 119.89(13) ?
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
O4 C13 C14 . . 124.18(12) ?
O4 C13 C12 . . 115.47(12) ?
C14 C13 C12 . . 120.34(12) ?
C13 C14 C15 . . 119.51(12) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
O3 C15 C14 . . 120.93(12) ?
O3 C15 C10 . . 117.50(12) ?
C14 C15 C10 . . 121.57(12) ?
O4 C16 H16A . . 109.5 ?
O4 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O4 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C1 O1 C8 . . 106.42(10) ?
C15 O3 H3A . . 110.1(13) ?
C13 O4 C16 . . 117.98(11) ?
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
C1 O1 . 1.3764(15) ?
C1 C6 . 1.3781(19) ?
C1 C2 . 1.3782(19) ?
C2 C3 . 1.374(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.389(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.370(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.3927(18) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.4495(18) ?
C7 O2 . 1.2280(16) ?
C7 C8 . 1.4697(18) ?
C8 C9 . 1.3370(17) ?
C8 O1 . 1.3902(15) ?
C9 C10 . 1.4373(17) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.4014(18) ?
C10 C15 . 1.4046(18) ?
C11 C12 . 1.3696(18) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.3876(19) ?
C12 H12 . 0.9300 ?
C13 O4 . 1.3588(16) ?
C13 C14 . 1.3758(18) ?
C14 C15 . 1.3868(18) ?
C14 H14 . 0.9300 ?
C15 O3 . 1.3533(16) ?
C16 O4 . 1.4203(17) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
O3 H3A . 0.90(2) ?
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
O3 H3A O2 2_554 0.90(2) 1.80(2) 2.6952(14) 170.0(19)
C16 H16A O3 2_554 0.96 2.59 3.3328(14) 135
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
O1 C1 C2 C3 . . . . -179.59(12) ?
C6 C1 C2 C3 . . . . 0.2(2) ?
C1 C2 C3 C4 . . . . -0.8(2) ?
C2 C3 C4 C5 . . . . 0.9(2) ?
C3 C4 C5 C6 . . . . -0.4(2) ?
O1 C1 C6 C5 . . . . -179.94(11) ?
C2 C1 C6 C5 . . . . 0.23(19) ?
O1 C1 C6 C7 . . . . 0.83(14) ?
C2 C1 C6 C7 . . . . -178.99(12) ?
C4 C5 C6 C1 . . . . -0.12(19) ?
C4 C5 C6 C7 . . . . 178.85(14) ?
C1 C6 C7 O2 . . . . 179.03(14) ?
C5 C6 C7 O2 . . . . 0.0(3) ?
C1 C6 C7 C8 . . . . -0.86(14) ?
C5 C6 C7 C8 . . . . -179.93(14) ?
O2 C7 C8 C9 . . . . 0.9(2) ?
C6 C7 C8 C9 . . . . -179.20(12) ?
O2 C7 C8 O1 . . . . -179.27(13) ?
C6 C7 C8 O1 . . . . 0.63(14) ?
O1 C8 C9 C10 . . . . 0.5(2) ?
C7 C8 C9 C10 . . . . -179.69(12) ?
C8 C9 C10 C11 . . . . 2.7(2) ?
C8 C9 C10 C15 . . . . -179.18(13) ?
C15 C10 C11 C12 . . . . -0.59(19) ?
C9 C10 C11 C12 . . . . 177.54(13) ?
C10 C11 C12 C13 . . . . 0.2(2) ?
C11 C12 C13 O4 . . . . -178.96(13) ?
C11 C12 C13 C14 . . . . 0.4(2) ?
O4 C13 C14 C15 . . . . 178.78(12) ?
C12 C13 C14 C15 . . . . -0.47(19) ?
C13 C14 C15 O3 . . . . -179.95(11) ?
C13 C14 C15 C10 . . . . 0.05(18) ?
C11 C10 C15 O3 . . . . -179.53(11) ?
C9 C10 C15 O3 . . . . 2.24(17) ?
C11 C10 C15 C14 . . . . 0.47(18) ?
C9 C10 C15 C14 . . . . -177.76(11) ?
C6 C1 O1 C8 . . . . -0.43(14) ?
C2 C1 O1 C8 . . . . 179.39(12) ?
C9 C8 O1 C1 . . . . 179.68(12) ?
C7 C8 O1 C1 . . . . -0.15(13) ?
C14 C13 O4 C16 . . . . 2.1(2) ?
C12 C13 O4 C16 . . . . -178.64(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28669650
