cif

############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # Copyright International Union of Crystallography # # # ##############################################################################

### 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

_publ_author
_name | _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

### 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

_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 MoKα
_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 φ scans and ω scans with κ 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 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>2σ(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/[σ2(Fo2)+(0.0521P)2+0.4437P] where P = (Fo2+2Fc2)/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 ?

_atom_type
_symbol | _description | _scat_dispersion_real | _scat_dispersion_imag | _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

_atom_site
_label | _fract_x | _fract_y | _fract_z | _U_iso_or_equiv | _adp_type | _calc_flag | _refinement_flags | _occupancy | _disorder_assembly | _disorder_group | _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

_atom_site_aniso
_label | _U_11 | _U_22 | _U_33 | _U_12 | _U_13 | _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.

_geom_bond
_atom_site_label_1 | _atom_site_label_2 | _site_symmetry_2 | _distance | _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 | ?

_geom_angle
_atom_site_label_1 | _atom_site_label_2 | _atom_site_label_3 | _site_symmetry_1 | _site_symmetry_3 |  | _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) | ?

_geom_hbond
_atom_site_label_D | _atom_site_label_H | _atom_site_label_A | _site_symmetry_A | _distance_DH | _distance_HA | _distance_DA | _angle_DHA
--- | --- | --- | --- | --- | --- | --- | ---
O1 | H1O | O2 | 3_645 | 0.97(2) | 1.74(2) | 2.7095(14) | 176(2)