#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/61/2236162.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_2236162
loop_
_publ_author_name
'Pereira, Jorge L.'
'Teixeira, Róbson R.'
'Guilardi, Silvana'
'Paixão, Drielly A.'
_publ_section_title
;
 6-Methoxyisobenzofuran-1(3H)-one
;
_journal_coeditor_code           CV5338
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2995
_journal_paper_doi               10.1107/S1600536812039074
_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_name_systematic
;
6-Methoxyisobenzofuran-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                 90.471(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2922(19)
_cell_length_b                   8.4982(12)
_cell_length_c                   9.786(2)
_cell_measurement_reflns_used    3082
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.10
_cell_volume                     772.7(2)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  '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  0.0363
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3304
_diffrn_reflns_reduction_process
;
Scaled and merged with Sortav
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0504
_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)+(0.0943P)²+0.0320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1659
_reflns_number_gt                1285
_reflns_number_total             1741
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cv5338.cif
_cod_data_source_block           I
_cod_original_cell_volume        772.8(2)
_cod_database_code               2236162
_cod_database_fobs_code          2236162
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 O1 0.93834(12) 0.04009(14) 0.16871(11) 0.0695(4) Uani d . 1
O O2 0.79489(14) -0.11746(14) 0.04458(12) 0.0752(4) Uani d . 1
O O3 0.54600(12) 0.40633(13) -0.19372(11) 0.0699(4) Uani d . 1
C C1 0.83141(17) 0.0134(2) 0.07489(15) 0.0612(4) Uani d . 1
C C2 0.77893(16) 0.16711(17) 0.02593(13) 0.0552(4) Uani d . 1
C C3 0.67205(15) 0.19885(18) -0.07089(14) 0.0569(4) Uani d . 1
H H3 0.6212 0.1185 -0.114 0.068 Uiso calc R 1
C C4 0.64497(16) 0.35569(18) -0.09995(14) 0.0568(4) Uani d . 1
C C5 0.72174(17) 0.47477(18) -0.03217(16) 0.0632(4) Uani d . 1
H H5 0.7013 0.5794 -0.0524 0.076 Uiso calc R 1
C C6 0.82660(17) 0.44069(19) 0.06357(16) 0.0639(4) Uani d . 1
H H6 0.8766 0.5208 0.108 0.077 Uiso calc R 1
C C7 0.85594(16) 0.28364(18) 0.09213(14) 0.0572(4) Uani d . 1
C C8 0.96195(18) 0.2080(2) 0.18656(16) 0.0663(5) Uani d . 1
H H8A 1.0596 0.2365 0.1624 0.08 Uiso calc R 1
H H8B 0.9448 0.2392 0.2804 0.08 Uiso calc R 1
C C9 0.45913(19) 0.2893(2) -0.25875(18) 0.0730(5) Uani d . 1
H H9A 0.3942 0.3389 -0.3222 0.11 Uiso calc R 1
H H9B 0.4051 0.2336 -0.191 0.11 Uiso calc R 1
H H9C 0.5197 0.2169 -0.3067 0.11 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 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
C1 O1 C8 110.59(12)
C4 O3 C9 117.14(13)
O2 C1 O1 121.50(16)
O2 C1 C2 130.52(17)
O1 C1 C2 107.98(14)
C7 C2 C3 122.97(15)
C7 C2 C1 108.34(15)
C3 C2 C1 128.69(14)
C4 C3 C2 116.94(14)
C4 C3 H3 121.5
C2 C3 H3 121.5
O3 C4 C3 124.20(14)
O3 C4 C5 115.37(14)
C3 C4 C5 120.43(15)
C6 C5 C4 121.64(15)
C6 C5 H5 119.2
C4 C5 H5 119.2
C5 C6 C7 118.38(15)
C5 C6 H6 120.8
C7 C6 H6 120.8
C2 C7 C6 119.63(15)
C2 C7 C8 108.60(14)
C6 C7 C8 131.77(14)
O1 C8 C7 104.50(12)
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.366(2)
O1 C8 1.454(2)
O2 C1 1.199(2)
O3 C4 1.3635(19)
O3 C9 1.427(2)
C1 C2 1.473(2)
C2 C7 1.380(2)
C2 C3 1.393(2)
C3 C4 1.385(2)
C3 H3 0.93
C4 C5 1.402(2)
C5 C6 1.377(2)
C5 H5 0.93
C6 C7 1.390(2)
C6 H6 0.93
C7 C8 1.491(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
C9 H9B O2 3_655 0.96 2.55 3.490(2) 164.9
C8 H8B Cg1 4_575 0.97 2.84 3.637(2) 140.0
C9 H9C Cg1 4_576 0.96 2.91 3.744(2) 146.0
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
C8 O1 C1 O2 179.83(13)
C8 O1 C1 C2 -0.01(16)
O2 C1 C2 C7 -179.93(15)
O1 C1 C2 C7 -0.11(16)
O2 C1 C2 C3 -0.6(3)
O1 C1 C2 C3 179.23(12)
C7 C2 C3 C4 0.2(2)
C1 C2 C3 C4 -179.01(12)
C9 O3 C4 C3 4.2(2)
C9 O3 C4 C5 -176.13(13)
C2 C3 C4 O3 178.74(12)
C2 C3 C4 C5 -0.9(2)
O3 C4 C5 C6 -178.97(12)
C3 C4 C5 C6 0.7(2)
C4 C5 C6 C7 0.2(2)
C3 C2 C7 C6 0.6(2)
C1 C2 C7 C6 179.99(12)
C3 C2 C7 C8 -179.21(12)
C1 C2 C7 C8 0.18(16)
C5 C6 C7 C2 -0.8(2)
C5 C6 C7 C8 178.95(14)
C1 O1 C8 C7 0.11(15)
C2 C7 C8 O1 -0.18(15)
C6 C7 C8 O1 -179.96(14)
