#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/79/2007990.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_2007990
loop_
_publ_author_name
'Iida, Katsumi'
'Kawata, Etsuya'
'Komada, Kaori'
'Saito, Masaichi'
'Kumakura, Shigekazu'
'Yoshioka, Michikazu'
_publ_section_title
;Highly Strained C---C Bonds:
 3-(1'-Hydroxy-4'-isopropyl-2',2'-dimethyl-1',2'-dihydrobenzocyclobuten-1'-yl)-3-methyl-2-butanone
 Ethylene Acetal, (I), and
 (3S^*^,1'S^*^)-3-Acetoxy-2-(1'-hydroxy-1',2'-dihydrobenzocyclobuten-1'-yl)-2-methylpentane,
 (II)
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1938
_journal_page_last               1941
_journal_paper_doi               10.1107/S0108270198009895
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac          'C16 H22 O3'
_chemical_formula_moiety         'C16 H22 O3'
_chemical_formula_sum            'C16 H22 O3'
_chemical_formula_weight         262.35
_chemical_name_systematic
;
(3S^*^,1'3S^*^)-3-acetoxy-2-(1'-hydroxy-1',2'
-dihydrobenzocyclobuten-1'-yl)-2-methylpentane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source           'International Tables Vol. IV'
_cell_angle_alpha                85.22(7)
_cell_angle_beta                 88.89(7)
_cell_angle_gamma                77.23(3)
_cell_formula_units_Z            2
_cell_length_a                   7.500(2)
_cell_length_b                   8.505(2)
_cell_length_c                   11.852(5)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    298
_cell_measurement_theta_max      31
_cell_measurement_theta_min      1
_cell_volume                     734.7(4)
_computing_cell_refinement       'DENZO (Mac Science, 1996)'
_computing_data_collection       'XDIP (Mac Science, 1996)'
_computing_data_reduction        'DENZO (Mac Science, 1996)'
_computing_molecular_graphics    'ORTEP (Johnson, 1970)'
_computing_publication_material  'CRYSTAN-GM (Mac Science, 1996)'
_computing_structure_refinement  'CRYSTAN-GM (Mac Science, 1996)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.8832
_diffrn_measured_fraction_theta_max 0.9446
_diffrn_measurement_device_type  'Mac Science DIP3000'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7516
_diffrn_reflns_theta_full        ' 31.00 '
_diffrn_reflns_theta_max         ' 30.18 '
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.612
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2819
_refine_ls_R_factor_gt           0.060
_refine_ls_shift/su_max          0.0080
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
'w = exp(10.0sin²θ/λ²)/(σ²(Fo)+0.001(Fo)²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.070
_reflns_number_gt                2819
_reflns_number_total             4417
_reflns_threshold_expression     I>1σ(I)
_cod_data_source_file            oa1055.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w =
exp(10.0sin^2^\q/\l^2^)/(\s^2^(Fo)+0.001(Fo)^2^)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w =
exp(10.0sin^2^\q/\l^2^)/(\s^2^(Fo)+0.001(Fo)^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      ' P -1 '
_cod_original_formula_sum        'C16 H22 O3 '
_cod_database_code               2007990
loop_
_symmetry_equiv_pos_as_xyz
' +x, +y, +z '
' -x, -y, -z '
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_type_symbol
O1 1.08190(4) -0.30350(3) 0.34240(3) 0.05390(10) Uani O
O2 0.62400(4) -0.27370(3) 0.29470(2) 0.05030(10) Uani O
O3 0.77290(5) -0.41780(4) 0.44580(3) 0.0642(2) Uani O
C1 0.97090(6) 0.07020(4) 0.32850(3) 0.0490(2) Uani C
C2 1.07990(5) -0.03390(4) 0.25950(3) 0.04580(10) Uani C
C3 1.23280(6) 0.00230(5) 0.20580(4) 0.0559(2) Uani C
C4 1.26570(7) 0.15410(5) 0.22370(4) 0.0641(2) Uani C
C5 1.15580(7) 0.25920(5) 0.29220(4) 0.0660(2) Uani C
C6 1.00340(7) 0.22030(5) 0.34740(4) 0.0597(2) Uani C
C7 0.84500(6) -0.04360(4) 0.36140(3) 0.0516(2) Uani C
C8 0.97060(5) -0.16600(4) 0.28220(3) 0.04410(10) Uani C
C9 0.88010(5) -0.21520(4) 0.17800(3) 0.04590(10) Uani C
C10 0.76000(7) -0.06570(5) 0.11400(4) 0.0603(2) Uani C
C11 1.03240(7) -0.29360(6) 0.09870(4) 0.0625(2) Uani C
C12 0.76690(5) -0.34190(4) 0.21610(3) 0.0484(2) Uani C
C13 0.66700(8) -0.40160(6) 0.12300(4) 0.0666(2) Uani C
C14 0.57600(11) -0.53740(9) 0.16700(6) 0.0972(4) Uani C
C15 0.63950(6) -0.32520(5) 0.40480(3) 0.0532(2) Uani C
C16 0.47400(8) -0.25160(8) 0.46960(4) 0.0732(3) Uani C
H1 1.0126(10) -0.3507(9) 0.3819(6) 0.073(2) Uiso H
H3 1.3119(10) -0.0694(8) 0.1614(6) 0.065(2) Uiso H
H4 1.3748(10) 0.1755(9) 0.1894(6) 0.072(2) Uiso H
H5 1.1864(10) 0.3627(9) 0.2989(7) 0.077(2) Uiso H
H6 0.9212(9) 0.2956(8) 0.3943(5) 0.0610(10) Uiso H
H7A 0.8490(8) -0.0810(7) 0.4416(5) 0.0570(10) Uiso H
H7B 0.7098(9) -0.0080(7) 0.3378(5) 0.0600(10) Uiso H
H10A 0.7067(11) -0.0904(10) 0.0437(7) 0.085(2) Uiso H
H10B 0.8253(11) 0.0135(10) 0.0976(7) 0.083(2) Uiso H
H10C 0.6587(10) -0.0166(9) 0.1604(6) 0.071(2) Uiso H
H11A 0.9780(11) -0.3174(10) 0.0267(7) 0.084(2) Uiso H
H11B 1.1010(13) -0.3840(12) 0.1378(8) 0.096(2) Uiso H
H11C 1.1207(10) -0.2204(9) 0.0808(6) 0.075(2) Uiso H
H12 0.8472(7) -0.4310(7) 0.2536(4) 0.0450(10) Uiso H
H13A 0.7556(10) -0.4380(9) 0.0656(7) 0.076(2) Uiso H
H13B 0.5766(10) -0.3078(9) 0.0886(6) 0.067(2) Uiso H
H14A 0.5173 -0.5748 0.1090 0.134 Uiso H
H14B 0.492 -0.495 0.236 0.141 Uiso H
H14C 0.6787 -0.6259 0.2049 0.141 Uiso H
H16A 0.5000 -0.2771 0.5468 0.105 Uiso H
H16B 0.3636 -0.2966 0.4418 0.123 Uiso H
H16C 0.444 -0.139 0.450 0.147 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
C8 O1 H1 107.6(6) no
C12 O2 C15 119.40(10) no
C2 C1 C6 122.80(10) yes
C2 C1 C7 94.50(10) yes
C6 C1 C7 142.60(10) yes
C1 C2 C3 122.20(10) yes
C1 C2 C8 93.70(10) yes
C3 C2 C8 144.00(10) yes
C2 C3 C4 115.30(10) yes
C3 C4 C5 122.50(10) yes
C4 C5 C6 121.60(10) yes
C1 C6 C5 115.50(10) yes
C1 C7 C8 86.10(10) yes
O1 C8 C2 109.40(10) yes
O1 C8 C7 114.10(10) yes
O1 C8 C9 111.10(10) no
C2 C8 C7 85.70(10) yes
C2 C8 C9 116.50(10) no
C7 C8 C9 117.80(10) no
C8 C9 C10 110.50(10) no
C8 C9 C11 108.20(10) no
C8 C9 C12 110.00(10) no
C10 C9 C11 109.00(10) no
C10 C9 C12 111.00(10) no
C11 C9 C12 108.10(10) no
O2 C12 C9 109.80(10) no
O2 C12 C13 105.10(10) no
C9 C12 C13 116.40(10) no
C12 C13 C14 112.30(10) no
O2 C15 O3 123.80(10) no
O2 C15 C16 111.40(10) no
O3 C15 C16 124.80(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . . 1.4230(10) yes
O1 H1 . . .838(8) no
O2 C12 . . 1.4590(10) no
O2 C15 . . 1.3400(10) no
O2 H12 . . 1.979(6) no
O3 C15 . . 1.2100(10) no
C1 C2 . . 1.3770(10) yes
C1 C6 . . 1.3880(10) yes
C1 C7 . . 1.5190(10) yes
C2 C3 . . 1.3820(10) yes
C2 C8 . . 1.5350(10) yes
C3 C4 . . 1.4000(10) yes
C4 C5 . . 1.3810(10) yes
C5 C6 . . 1.3950(10) yes
C7 C8 . . 1.5960(10) yes
C8 C9 . . 1.5510(10) no
C8 H1 . . 1.857(8) no
C9 C10 . . 1.5370(10) no
C9 C11 . . 1.5360(10) no
C9 C12 . . 1.5470(10) no
C12 C13 . . 1.5270(10) no
C13 C14 . . 1.5190(10) no
C15 C16 . . 1.4910(10) no
