#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/67/2226759.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_2226759
loop_
_publ_author_name
'Liu, Dongze'
_publ_section_title
;
 3-Hydroxy-8-oxo-3-nor-methylchamigrane-2,7-peroxide
;
_journal_coeditor_code           ZS2044
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1875
_journal_paper_doi               10.1107/S1600536810024517
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H22 O4'
_chemical_formula_moiety         'C14 H22 O4'
_chemical_formula_sum            'C14 H22 O4'
_chemical_formula_weight         254.32
_chemical_name_systematic
;
9-hydroxy-1,5,5-trimethyl-1,8-epidioxyspiro[5.5]decan-2-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3138(4)
_cell_length_b                   12.4206(7)
_cell_length_c                   13.9408(8)
_cell_measurement_reflns_used    4034
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.79
_cell_volume                     1266.41(12)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6456
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9671
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0611P)²+0.2837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                1471
_reflns_number_total             1602
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2044.cif
_cod_data_source_block           I
_cod_database_code               2226759
_cod_database_fobs_code          2226759
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'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4858(3) 0.29411(15) 0.68490(13) 0.0218(4) Uani d . 1 . .
H H1A 0.5496 0.2309 0.7124 0.026 Uiso calc R 1 . .
H H1B 0.3532 0.2857 0.6971 0.026 Uiso calc R 1 . .
C C2 0.5204(3) 0.29930(15) 0.57779(13) 0.0225(4) Uani d . 1 . .
H H2 0.4747 0.2304 0.5495 0.027 Uiso calc R 1 . .
C C3 0.4112(3) 0.39043(16) 0.53239(13) 0.0247(4) Uani d . 1 . .
H H3 0.2786 0.3719 0.5380 0.030 Uiso calc R 1 . .
C C4 0.4405(3) 0.49914(16) 0.58127(15) 0.0296(5) Uani d . 1 . .
H H4A 0.3429 0.5494 0.5608 0.036 Uiso calc R 1 . .
H H4B 0.5591 0.5295 0.5602 0.036 Uiso calc R 1 . .
C C5 0.4393(3) 0.49050(15) 0.69173(14) 0.0259(4) Uani d . 1 . .
H H5A 0.3114 0.4812 0.7134 0.031 Uiso calc R 1 . .
H H5B 0.4846 0.5593 0.7187 0.031 Uiso calc R 1 . .
C C6 0.5554(2) 0.39771(14) 0.73338(13) 0.0183(4) Uani d . 1 . .
C C7 0.7632(3) 0.40990(16) 0.70409(13) 0.0229(4) Uani d . 1 . .
C C8 0.8819(3) 0.32554(18) 0.75389(15) 0.0280(4) Uani d . 1 . .
C C9 0.8623(3) 0.3215(2) 0.86128(15) 0.0334(5) Uani d . 1 . .
H H9A 0.9072 0.3896 0.8897 0.040 Uiso calc R 1 . .
H H9B 0.9367 0.2617 0.8873 0.040 Uiso calc R 1 . .
C C10 0.6617(3) 0.30478(17) 0.88798(14) 0.0285(4) Uani d . 1 . .
H H10A 0.6507 0.3054 0.9588 0.034 Uiso calc R 1 . .
H H10B 0.6229 0.2328 0.8653 0.034 Uiso calc R 1 . .
C C11 0.5305(3) 0.38957(16) 0.84637(14) 0.0221(4) Uani d . 1 . .
C C12 0.3354(3) 0.3526(2) 0.87222(16) 0.0331(5) Uani d . 1 . .
H H12A 0.3233 0.3480 0.9421 0.050 Uiso calc R 1 . .
H H12B 0.3122 0.2817 0.8438 0.050 Uiso calc R 1 . .
H H12C 0.2467 0.4046 0.8472 0.050 Uiso calc R 1 . .
C C13 0.5579(3) 0.49723(17) 0.89893(14) 0.0312(5) Uani d . 1 . .
H H13A 0.6821 0.5238 0.8871 0.047 Uiso calc R 1 . .
H H13B 0.5401 0.4866 0.9679 0.047 Uiso calc R 1 . .
H H13C 0.4691 0.5499 0.8752 0.047 Uiso calc R 1 . .
C C14 0.8524(3) 0.52104(18) 0.72087(16) 0.0341(5) Uani d . 1 . .
H H14A 0.7730 0.5775 0.6949 0.051 Uiso calc R 1 . .
H H14B 0.9713 0.5235 0.6885 0.051 Uiso calc R 1 . .
H H14C 0.8695 0.5326 0.7898 0.051 Uiso calc R 1 . .
O O1 0.7133(2) 0.30323(12) 0.56148(10) 0.0295(4) Uani d . 1 . .
O O2 0.4515(2) 0.40426(12) 0.43304(10) 0.0333(4) Uani d . 1 . .
H H2A 0.4353 0.3457 0.4041 0.050 Uiso calc R 1 . .
O O3 0.7841(2) 0.40379(13) 0.60137(10) 0.0298(3) Uani d . 1 . .
O O4 0.9872(2) 0.26855(15) 0.71020(12) 0.0423(5) Uani d . 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 0.0000 '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 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 109.98(15) ?
C2 C1 H1A . . 109.7 ?
C6 C1 H1A . . 109.7 ?
C2 C1 H1B . . 109.7 ?
C6 C1 H1B . . 109.7 ?
H1A C1 H1B . . 108.2 ?
O1 C2 C1 . . 108.82(16) ?
O1 C2 C3 . . 115.22(17) ?
C1 C2 C3 . . 110.70(16) ?
O1 C2 H2 . . 107.3 ?
C1 C2 H2 . . 107.3 ?
C3 C2 H2 . . 107.3 ?
O2 C3 C2 . . 112.61(17) ?
O2 C3 C4 . . 107.32(16) ?
C2 C3 C4 . . 113.44(16) ?
O2 C3 H3 . . 107.7 ?
C2 C3 H3 . . 107.7 ?
C4 C3 H3 . . 107.7 ?
C3 C4 C5 . . 112.51(16) ?
C3 C4 H4A . . 109.1 ?
C5 C4 H4A . . 109.1 ?
C3 C4 H4B . . 109.1 ?
C5 C4 H4B . . 109.1 ?
H4A C4 H4B . . 107.8 ?
C4 C5 C6 . . 115.08(16) ?
C4 C5 H5A . . 108.5 ?
C6 C5 H5A . . 108.5 ?
C4 C5 H5B . . 108.5 ?
C6 C5 H5B . . 108.5 ?
H5A C5 H5B . . 107.5 ?
C1 C6 C5 . . 106.09(15) ?
C1 C6 C7 . . 106.51(15) ?
C5 C6 C7 . . 111.08(16) ?
C1 C6 C11 . . 110.13(15) ?
C5 C6 C11 . . 110.94(15) ?
C7 C6 C11 . . 111.84(15) ?
O3 C7 C8 . . 110.81(16) ?
O3 C7 C14 . . 98.79(15) ?
C8 C7 C14 . . 107.71(16) ?
O3 C7 C6 . . 110.67(15) ?
C8 C7 C6 . . 111.29(16) ?
C14 C7 C6 . . 116.91(17) ?
O4 C8 C9 . . 122.8(2) ?
O4 C8 C7 . . 122.27(19) ?
C9 C8 C7 . . 114.91(18) ?
C8 C9 C10 . . 109.78(18) ?
C8 C9 H9A . . 109.7 ?
C10 C9 H9A . . 109.7 ?
C8 C9 H9B . . 109.7 ?
C10 C9 H9B . . 109.7 ?
H9A C9 H9B . . 108.2 ?
C9 C10 C11 . . 114.46(17) ?
C9 C10 H10A . . 108.6 ?
C11 C10 H10A . . 108.6 ?
C9 C10 H10B . . 108.6 ?
C11 C10 H10B . . 108.6 ?
H10A C10 H10B . . 107.6 ?
C13 C11 C10 . . 109.54(16) ?
C13 C11 C12 . . 105.55(17) ?
C10 C11 C12 . . 106.57(17) ?
C13 C11 C6 . . 113.71(16) ?
C10 C11 C6 . . 110.25(15) ?
C12 C11 C6 . . 110.88(16) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C7 C14 H14A . . 109.5 ?
C7 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C7 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C2 O1 O3 . . 108.54(14) ?
C3 O2 H2A . . 109.5 ?
C7 O3 O1 . . 112.66(14) ?
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
C1 C2 . 1.516(3) ?
C1 C6 . 1.540(2) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 O1 . 1.430(2) ?
C2 C3 . 1.523(3) ?
C2 H2 . 1.0000 ?
C3 O2 . 1.426(2) ?
C3 C4 . 1.528(3) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.544(3) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.545(3) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.581(3) ?
C6 C11 . 1.589(2) ?
C7 O3 . 1.442(2) ?
C7 C8 . 1.527(3) ?
C7 C14 . 1.545(3) ?
C8 O4 . 1.211(3) ?
C8 C9 . 1.505(3) ?
C9 C10 . 1.528(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.538(3) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C13 . 1.538(3) ?
C11 C12 . 1.542(3) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
O1 O3 . 1.462(2) ?
O2 H2A . 0.8400 ?
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
_geom_hbond_publ_flag
O2 H2A O1 4_456 0.84 2.51 3.112(2) 130 yes
O2 H2A O4 4_456 0.84 2.17 2.943(2) 154 yes
C2 H2 O1 4_456 1.00 2.49 3.231(2) 130 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 O1 . . . . 63.6(2) ?
C6 C1 C2 C3 . . . . -63.9(2) ?
O1 C2 C3 O2 . . . . 50.9(2) ?
C1 C2 C3 O2 . . . . 174.94(16) ?
O1 C2 C3 C4 . . . . -71.2(2) ?
C1 C2 C3 C4 . . . . 52.8(2) ?
O2 C3 C4 C5 . . . . -168.47(18) ?
C2 C3 C4 C5 . . . . -43.4(3) ?
C3 C4 C5 C6 . . . . 46.4(3) ?
C2 C1 C6 C5 . . . . 63.35(19) ?
C2 C1 C6 C7 . . . . -55.08(19) ?
C2 C1 C6 C11 . . . . -176.53(15) ?
C4 C5 C6 C1 . . . . -55.3(2) ?
C4 C5 C6 C7 . . . . 60.0(2) ?
C4 C5 C6 C11 . . . . -174.90(17) ?
C1 C6 C7 O3 . . . . 52.6(2) ?
C5 C6 C7 O3 . . . . -62.5(2) ?
C11 C6 C7 O3 . . . . 172.94(15) ?
C1 C6 C7 C8 . . . . -71.10(18) ?
C5 C6 C7 C8 . . . . 173.81(15) ?
C11 C6 C7 C8 . . . . 49.3(2) ?
C1 C6 C7 C14 . . . . 164.57(16) ?
C5 C6 C7 C14 . . . . 49.5(2) ?
C11 C6 C7 C14 . . . . -75.1(2) ?
O3 C7 C8 O4 . . . . 5.0(3) ?
C14 C7 C8 O4 . . . . -102.0(2) ?
C6 C7 C8 O4 . . . . 128.6(2) ?
O3 C7 C8 C9 . . . . -176.93(18) ?
C14 C7 C8 C9 . . . . 76.0(2) ?
C6 C7 C8 C9 . . . . -53.3(2) ?
O4 C8 C9 C10 . . . . -126.6(2) ?
C7 C8 C9 C10 . . . . 55.4(3) ?
C8 C9 C10 C11 . . . . -56.0(3) ?
C9 C10 C11 C13 . . . . -72.0(2) ?
C9 C10 C11 C12 . . . . 174.30(18) ?
C9 C10 C11 C6 . . . . 53.9(2) ?
C1 C6 C11 C13 . . . . -167.83(16) ?
C5 C6 C11 C13 . . . . -50.7(2) ?
C7 C6 C11 C13 . . . . 73.9(2) ?
C1 C6 C11 C10 . . . . 68.7(2) ?
C5 C6 C11 C10 . . . . -174.15(16) ?
C7 C6 C11 C10 . . . . -49.5(2) ?
C1 C6 C11 C12 . . . . -49.1(2) ?
C5 C6 C11 C12 . . . . 68.1(2) ?
C7 C6 C11 C12 . . . . -167.31(16) ?
C1 C2 O1 O3 . . . . -64.81(18) ?
C3 C2 O1 O3 . . . . 60.17(19) ?
C8 C7 O3 O1 . . . . 66.13(19) ?
C14 C7 O3 O1 . . . . 178.97(15) ?
C6 C7 O3 O1 . . . . -57.8(2) ?
C2 O1 O3 C7 . . . . 64.05(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29214914
