#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/70/2237098.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_2237098
loop_
_publ_author_name
'Paixão, Drielly A.'
'Guilardi, Silvana'
'Pereira, Jorge L.'
'Teixeira, Róbson R.'
'Arantes, Júnior F.'
_publ_section_title
;
 5-Methoxy-2-benzofuran-1(3H)-one
;
_journal_coeditor_code           ZS2239
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3288
_journal_paper_doi               10.1107/S1600536812044789
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C9 H8 O3'
_chemical_formula_moiety         'C9 H8 O3'
_chemical_formula_sum            'C9 H8 O3'
_chemical_formula_weight         164.15
_chemical_melting_point_gt       386.4
_chemical_melting_point_lt       386.7
_chemical_name_systematic
;
5-Methoxy-2-benzofuran-1(3H)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.962(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1819(9)
_cell_length_b                   10.4285(18)
_cell_length_c                   9.2965(9)
_cell_measurement_reflns_used    1685
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      3.2
_cell_volume                     781.26(18)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_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_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Enraf--Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14100
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0818P)²+0.0576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                1101
_reflns_number_total             1587
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2239.cif
_cod_data_source_block           I
_cod_database_code               2237098
_cod_database_fobs_code          2237098
loop_
_space_group_symop_operation_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
O O3 0.37522(15) -0.24147(11) 0.61307(13) 0.0781(4) Uani d . 1
O O1 0.05757(18) 0.21719(13) 0.30246(15) 0.0903(5) Uani d . 1
C C7 0.16866(17) 0.02605(15) 0.40441(16) 0.0577(4) Uani d . 1
C C5 0.32245(19) -0.12294(14) 0.56458(16) 0.0591(4) Uani d . 1
C C3 0.3507(2) 0.10279(17) 0.61788(19) 0.0691(5) Uani d . 1
H H3 0.3971 0.17 0.6769 0.083 Uiso calc R 1
C C6 0.20840(18) -0.10008(15) 0.43826(16) 0.0578(4) Uani d . 1
H H6 0.1609 -0.1669 0.3791 0.069 Uiso calc R 1
O O2 0.1929(2) 0.35524(13) 0.46580(19) 0.1117(6) Uani d . 1
C C4 0.39278(19) -0.02130(16) 0.65283(17) 0.0662(4) Uani d . 1
H H4 0.4694 -0.0388 0.7367 0.079 Uiso calc R 1
C C2 0.2366(2) 0.12584(14) 0.49162(18) 0.0631(4) Uani d . 1
C C8 0.0518(2) 0.07991(17) 0.27798(19) 0.0757(5) Uani d . 1
H H8A 0.0874 0.0587 0.1866 0.091 Uiso calc R 1
H H8B -0.0595 0.0471 0.2757 0.091 Uiso calc R 1
C C9 0.3066(3) -0.34911(17) 0.5294(2) 0.0956(7) Uani d . 1
H H9A 0.3534 -0.4266 0.5748 0.143 Uiso calc R 1
H H9B 0.3318 -0.3432 0.4325 0.143 Uiso calc R 1
H H9C 0.1884 -0.3501 0.5244 0.143 Uiso calc R 1
C C1 0.1678(3) 0.24532(17) 0.4269(2) 0.0804(6) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C5 O3 C9 117.55(14)
C1 O1 C8 110.05(13)
C2 C7 C6 122.13(14)
C2 C7 C8 108.56(14)
C6 C7 C8 129.31(14)
O3 C5 C6 124.38(14)
O3 C5 C4 114.75(14)
C6 C5 C4 120.87(15)
C4 C3 C2 118.08(15)
C4 C3 H3 121
C2 C3 H3 121
C7 C6 C5 117.03(14)
C7 C6 H6 121.5
C5 C6 H6 121.5
C3 C4 C5 121.14(15)
C3 C4 H4 119.4
C5 C4 H4 119.4
C7 C2 C3 120.75(15)
C7 C2 C1 108.43(16)
C3 C2 C1 130.82(16)
O1 C8 C7 104.45(14)
O1 C8 H8A 110.9
C7 C8 H8A 110.9
O1 C8 H8B 110.9
C7 C8 H8B 110.9
H8A C8 H8B 108.9
O3 C9 H9A 109.5
O3 C9 H9B 109.5
H9A C9 H9B 109.5
O3 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O2 C1 O1 120.56(18)
O2 C1 C2 131.0(2)
O1 C1 C2 108.49(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C5 1.3603(18)
O3 C9 1.425(2)
O1 C1 1.370(3)
O1 C8 1.449(2)
C7 C2 1.376(2)
C7 C6 1.378(2)
C7 C8 1.491(2)
C5 C6 1.388(2)
C5 C4 1.402(2)
C3 C4 1.364(2)
C3 C2 1.388(2)
C3 H3 0.93
C6 H6 0.93
O2 C1 1.209(2)
C4 H4 0.93
C2 C1 1.454(2)
C8 H8A 0.97
C8 H8B 0.97
C9 H9A 0.96
C9 H9B 0.96
C9 H9C 0.96
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
C6 H6 O1 2_545 0.93 2.54 3.419(2) 157
C8 H8A O2 4_565 0.97 2.52 3.372(2) 146
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
C9 O3 C5 C6 -1.0(2)
C9 O3 C5 C4 179.11(15)
C2 C7 C6 C5 -0.6(2)
C8 C7 C6 C5 -179.90(15)
O3 C5 C6 C7 -179.79(13)
C4 C5 C6 C7 0.1(2)
C2 C3 C4 C5 -0.3(2)
O3 C5 C4 C3 -179.70(13)
C6 C5 C4 C3 0.4(2)
C6 C7 C2 C3 0.7(2)
C8 C7 C2 C3 -179.91(15)
C6 C7 C2 C1 -179.22(13)
C8 C7 C2 C1 0.17(17)
C4 C3 C2 C7 -0.2(2)
C4 C3 C2 C1 179.72(15)
C1 O1 C8 C7 1.42(18)
C2 C7 C8 O1 -0.95(16)
C6 C7 C8 O1 178.38(14)
C8 O1 C1 O2 178.93(16)
C8 O1 C1 C2 -1.36(19)
C7 C2 C1 O2 -179.60(18)
C3 C2 C1 O2 0.5(3)
C7 C2 C1 O1 0.73(19)
C3 C2 C1 O1 -179.17(16)
