
data_global
_audit_creation_method SHELXTL-V5.1
_journal_date_recd_electronic 2002-03-21
_journal_date_accepted 2002-03-27
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2002
_journal_volume 58
_journal_issue 5
_journal_page_first o495
_journal_page_last o497
_journal_paper_category EO
_publ_contact_author_name 'Dr Lough, Alan J.'
_publ_contact_author_address 
;
Department of Chemistry
University of Toronto
Toronto
Ontario
Canada M5S 3H6
;
_publ_contact_author_email alough@chem.utoronto.ca
_publ_contact_author_fax '416 978 8775'
_publ_contact_author_phone '416 978 6275'
_publ_section_title 
;
2,3-Dihydro-2-hydroxybenzo[b]furan-3-one
;
loop_
_publ_author_name
_publ_author_address
'Kresge, A. J.' 
;
Department of Chemistry
University of Toronto
Toronto
Ontario
Canada M5S 3H6
;
'Lough, Alan J.' 
;
Department of Chemistry
University of Toronto
Toronto
Ontario
Canada M5S 3H6
;
'Meng, Q.' 
;
Department of Chemistry
University of Toronto
Toronto
Ontario
Canada M5S 3H6
;
data_7
_chemical_name_systematic 
;
2,3-Dihydro-2-hydroxybenzo[b]furan-3-one
;
_chemical_name_common ?
_chemical_formula_moiety 'C8 H6 O3'
_chemical_formula_sum 'C8 H6 O3'
_chemical_formula_iupac 'C8 H6 O3'
_chemical_formula_weight 150.13
_chemical_melting_point ?
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'P b c a'
_symmetry_space_group_name_Hall '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
_cell_length_a 11.0278(2)
_cell_length_b 7.7486(5)
_cell_length_c 15.7861(7)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1348.92(11)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 7696
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 27.5
_cell_measurement_temperature 150.0(10)
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.15
_exptl_crystal_density_diffrn 1.478
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 624
_exptl_absorpt_coefficient_mu 0.115
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details 
;
 ?
;
_diffrn_ambient_temperature 150.0(10)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_measurement_method '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number 7696
_diffrn_reflns_av_R_equivalents 0.028
_diffrn_reflns_av_sigmaI/netI 0.032
_diffrn_reflns_theta_min 2.6
_diffrn_reflns_theta_max 27.5
_diffrn_reflns_theta_full 27.46
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 20
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details 
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total 1535
_reflns_number_gt 1327
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.045
_refine_ls_R_factor_gt 0.038
_refine_ls_wR_factor_gt 0.100
_refine_ls_wR_factor_ref 0.106
_refine_ls_goodness_of_fit_ref 1.053
_refine_ls_restrained_S_all 1.053
_refine_ls_number_reflns 1535
_refine_ls_number_parameters 104
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.4437P] where P = (Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max <0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.341
_refine_diff_density_min -0.221
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
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'
_computing_data_collection 'COLLECT (Nonius, 1997-2001)'
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction DENZO-SMN
_computing_structure_solution 'SHELXTL (Sheldrick, 1999)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material SHELXTL
loop_
_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
_atom_site_type_symbol
O1 0.66766(9) 0.02384(12) 0.19807(6) 0.0315(3) Uani d . 1 . . O
H1O 0.598(2) -0.040(3) 0.2175(14) 0.074(7) Uiso d . 1 . . H
O2 0.52169(9) 0.33077(13) 0.24733(6) 0.0338(3) Uani d . 1 . . O
O3 0.74606(8) 0.05520(12) 0.33464(6) 0.0292(3) Uani d . 1 . . O
C1 0.69647(11) 0.14080(17) 0.25995(8) 0.0261(3) Uani d . 1 . . C
H1A 0.7587 0.2223 0.2372 0.031 Uiso calc R 1 . . H
C2 0.58810(11) 0.24633(16) 0.29350(8) 0.0244(3) Uani d . 1 . . C
C3 0.58586(11) 0.22090(15) 0.38411(8) 0.0227(3) Uani d . 1 . . C
C4 0.51013(11) 0.28465(17) 0.44799(8) 0.0263(3) Uani d . 1 . . C
H4A 0.4445 0.3596 0.4350 0.032 Uiso calc R 1 . . H
C5 0.53342(12) 0.23565(18) 0.53047(8) 0.0286(3) Uani d . 1 . . C
H5A 0.4839 0.2779 0.5751 0.034 Uiso calc R 1 . . H
C6 0.62978(12) 0.12377(17) 0.54846(8) 0.0293(3) Uani d . 1 . . C
H6A 0.6442 0.0918 0.6057 0.035 Uiso calc R 1 . . H
C7 0.70476(12) 0.05800(16) 0.48608(8) 0.0279(3) Uani d . 1 . . C
H7A 0.7696 -0.0182 0.4991 0.033 Uiso calc R 1 . . H
C8 0.68045(11) 0.10892(16) 0.40337(7) 0.0237(3) Uani d . 1 . . C
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
O1 0.0375(5) 0.0308(5) 0.0263(5) 0.0003(4) 0.0027(4) -0.0050(4)
O2 0.0400(6) 0.0371(6) 0.0243(5) 0.0123(4) -0.0023(4) 0.0030(4)
O3 0.0283(5) 0.0321(5) 0.0273(5) 0.0072(4) 0.0002(4) -0.0014(4)
C1 0.0283(6) 0.0261(6) 0.0239(6) 0.0004(5) 0.0018(5) 0.0005(5)
C2 0.0278(6) 0.0212(6) 0.0241(6) -0.0005(5) -0.0006(5) -0.0011(5)
C3 0.0244(6) 0.0207(6) 0.0230(6) -0.0017(4) -0.0008(5) 0.0003(5)
C4 0.0260(6) 0.0260(6) 0.0270(6) 0.0006(5) 0.0005(5) -0.0020(5)
C5 0.0321(6) 0.0299(7) 0.0236(6) -0.0048(5) 0.0034(5) -0.0031(5)
C6 0.0368(7) 0.0284(7) 0.0227(6) -0.0077(5) -0.0056(5) 0.0023(5)
C7 0.0291(6) 0.0249(6) 0.0295(6) -0.0009(5) -0.0076(5) 0.0021(5)
C8 0.0243(6) 0.0226(6) 0.0243(6) -0.0025(5) -0.0006(5) -0.0023(5)
_geom_special_details 
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1 C1 . 1.3699(15) y
O1 H1O . 0.97(2) ?
O2 C2 . 1.2230(15) y
O3 C8 . 1.3689(14) y
O3 C1 . 1.4592(15) y
C1 C2 . 1.5419(17) y
C1 H1A . 1.0000 ?
C2 C3 . 1.4441(17) y
C3 C8 . 1.3905(17) y
C3 C4 . 1.3994(18) ?
C4 C5 . 1.3803(18) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.4005(19) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.3831(19) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.3902(17) ?
C7 H7A . 0.9500 ?
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
C1 O1 H1O . . 107.4(13) ?
C8 O3 C1 . . 107.70(9) y
O1 C1 O3 . . 111.25(10) y
O1 C1 C2 . . 114.59(10) y
O3 C1 C2 . . 104.71(9) y
O1 C1 H1A . . 108.7 ?
O3 C1 H1A . . 108.7 ?
C2 C1 H1A . . 108.7 ?
O2 C2 C3 . . 130.77(12) y
O2 C2 C1 . . 122.90(11) y
C3 C2 C1 . . 106.33(10) ?
C8 C3 C4 . . 120.69(12) ?
C8 C3 C2 . . 106.79(11) ?
C4 C3 C2 . . 132.52(11) ?
C5 C4 C3 . . 118.13(12) ?
C5 C4 H4A . . 120.9 ?
C3 C4 H4A . . 120.9 ?
C4 C5 C6 . . 120.18(12) ?
C4 C5 H5A . . 119.9 ?
C6 C5 H5A . . 119.9 ?
C7 C6 C5 . . 122.50(12) ?
C7 C6 H6A . . 118.7 ?
C5 C6 H6A . . 118.7 ?
C6 C7 C8 . . 116.67(12) ?
C6 C7 H7A . . 121.7 ?
C8 C7 H7A . . 121.7 ?
O3 C8 C7 . . 123.79(11) ?
O3 C8 C3 . . 114.40(11) ?
C7 C8 C3 . . 121.81(12) ?
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
O1 H1O O2 3_645 0.97(2) 1.74(2) 2.7095(14) 176(2)