#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/92/2009254.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_2009254
loop_
_publ_author_name
'Khoo, Lian Ee'
'Hazell, Alan'
_publ_section_title
;
 3-Hydroxyphthalide and its adduct with dibutyltin oxide
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2070
_journal_page_last               2073
_journal_paper_doi               10.1107/S0108270199009282
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C8 H6 O3'
_chemical_formula_weight         150.14
_chemical_melting_point          368.0(10)
_chemical_name_systematic
;
3-hydroxyphthalide
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.0
_cell_angle_beta                 97.020(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   3.9463(6)
_cell_length_b                   11.423(2)
_cell_length_c                   7.3270(11)
_cell_measurement_reflns_used    4235
_cell_measurement_temperature    120
_cell_measurement_theta_max      34.1
_cell_measurement_theta_min      2.8
_cell_volume                     327.81(9)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics
;
      ORTEPIII (Burnett & Johnson, 1996), KRYSTAL
;
_computing_publication_material  KRYSTAL
_computing_structure_refinement  'modified ORFLS (1962), KRYSTAL'
_computing_structure_solution
;
     SIR97 (Cascarano et al., 1996), KRYSTAL
;
_diffrn_ambient_temperature      120
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method
;
ω rotation scans with narrow
frames
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6310
_diffrn_reflns_reduction_process 2204
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         2.8
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.27(4)
_refine_diff_density_min         -0.21(4)
_refine_ls_extinction_method
;
none
;
_refine_ls_goodness_of_fit_ref   1.700
_refine_ls_hydrogen_treatment    'see experimental'
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1004
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.028
_refine_ls_shift/su_max          0.00049
_refine_ls_shift/su_mean         0.00010
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/{[σcs(F²)+1.03F²]^1/2^-|F|}²'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.037
_reflns_number_gt                1004
_reflns_number_total             1006
_reflns_observed_criterion       I>0
_cod_data_source_file            fg1568.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '367-369' was changed to '368.0(10)'
- the average value was taken and precision was
estimated.

'_atom_site_thermal_displace_type' tag value 'Uij' was
replaced with 'Uani' value 11 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '367-369' was changed to '368.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '
1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^-|F|}^2^' was changed to 'calc'. New
tag '_refine_ls_weighting_details' was created. The value of the new
tag was set to 'w = 1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^-|F|}^2^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        327.80(9)
_cod_original_sg_symbol_Hall     'P 2y1'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2009254
_cod_database_fobs_code          2009254
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,1/2+y,-z
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 0.0275(5) 0.0187(5) 0.0157(5) -0.0026(4) -0.0046(4) 0.0000(4)
O2 0.0399(6) 0.0178(5) 0.0189(5) -0.0039(4) 0.0000(4) -0.0045(4)
O3 0.0212(5) 0.0160(5) 0.0194(5) -0.0005(4) -0.0013(3) 0.0065(4)
C1 0.0157(5) 0.0145(5) 0.0137(5) -0.0026(5) -0.0002(4) -0.0007(5)
C2 0.0135(5) 0.0161(5) 0.0147(5) -0.0009(5) 0.0008(4) 0.0025(5)
C3 0.0213(5) 0.0155(6) 0.0182(6) 0.0008(5) 0.0048(5) -0.0008(5)
C4 0.0252(6) 0.0206(6) 0.0141(6) -0.0031(5) 0.0014(5) -0.0027(5)
C5 0.0224(6) 0.0198(6) 0.0149(6) -0.0016(5) -0.0025(5) 0.0013(5)
C6 0.0191(5) 0.0146(6) 0.0174(6) -0.0005(5) -0.0011(4) 0.0008(5)
C7 0.0217(6) 0.0174(6) 0.0146(5) -0.0048(5) -0.0011(4) 0.0008(5)
C8 0.0164(5) 0.0171(6) 0.0167(6) 0.0003(5) -0.0009(4) 0.0030(5)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_type_symbol
O1 -0.0301(3) 0.1405 0.10780(10) 0.0212(5) Uani O
O2 0.1883(3) -0.04170(10) 0.13460(10) 0.0259(5) Uani O
O3 0.1309(2) 0.33620(10) 0.16420(10) 0.0192(5) Uani O
C1 0.2234(3) 0.0898(2) 0.3961(2) 0.0148(5) Uani C
C2 0.1071(3) 0.2034(2) 0.4110(2) 0.0148(5) Uani C
C3 0.1537(3) 0.26200(10) 0.5779(2) 0.0181(6) Uani C
C4 0.3235(4) 0.2030(2) 0.7284(2) 0.0201(6) Uani C
C5 0.4414(3) 0.0882(2) 0.7131(2) 0.0195(6) Uani C
C6 0.3924(3) 0.02960(10) 0.5456(2) 0.0173(6) Uani C
C7 0.1342(4) 0.0521(2) 0.2045(2) 0.0182(6) Uani C
C8 -0.0537(3) 0.24460(10) 0.2256(2) 0.0170(6) Uani C
HO3 0.022(6) 0.373(2) 0.082(4) 0.043(6) Uiso H
H3 0.0727 0.3397 0.5892 0.0218 Uiso H
H4 0.3602 0.2414 0.8440 0.0241 Uiso H
H5 0.5560 0.0500 0.8181 0.0234 Uiso H
H6 0.4710 -0.0483 0.5337 0.0208 Uiso H
H8 -0.2850 0.2664 0.2293 0.0205 Uiso H
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C8 110.80(10) no
C2 C1 C6 122.10(10) no
C2 C1 C7 107.90(10) no
C6 C1 C7 130.00(10) no
C1 C2 C3 120.80(10) no
C1 C2 C8 109.20(10) no
C3 C2 C8 129.90(10) no
C2 C3 C4 117.60(10) no
C3 C4 C5 121.50(10) no
C4 C5 C6 120.70(10) no
C1 C6 C5 117.20(10) no
O1 C7 O2 122.30(10) no
O2 C7 C1 128.80(10) no
O1 C7 C1 108.90(10) no
O1 C8 O3 110.30(10) no
O3 C8 C2 110.50(10) no
O1 C8 C2 103.10(10) no
C8 O3 HO3 113(2) no
C2 C3 H3 121.2 no
C4 C3 H3 121.2 no
C3 C4 H4 119.2 no
C5 C4 H4 119.2 no
C6 C5 H5 119.7 no
C4 C5 H5 119.7 no
C5 C6 H6 121.4 no
C1 C6 H6 121.4 no
O3 C8 H8 110.9 no
O1 C8 H8 110.9 no
C2 C8 H8 110.9 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.353(2) no
O1 C8 1.479(2) no
O2 C7 1.217(2) no
O3 C8 1.382(2) no
C1 C2 1.385(2) no
C1 C6 1.392(2) no
C1 C7 1.470(2) no
C2 C3 1.387(2) no
C2 C8 1.503(2) no
C3 C4 1.393(2) no
C4 C5 1.400(2) no
C5 C6 1.390(2) no
O3 HO3 0.82(3) no
C3 H3 0.950 no
C4 H4 0.950 no
C5 H5 0.950 no
C6 H6 0.950 no
C8 H8 0.950 no
