#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/68/2006826.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_2006826
loop_
_publ_author_name
'Bolte, Michael'
'Scholtyssik, Maria'
_publ_section_title
;
 A Tetragonal-Looking But Twinned Orthorhombic Structure
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1869
_journal_page_last               1871
_journal_paper_doi               10.1107/S0108270197009438
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C17 H24 O4'
_chemical_formula_weight         292.36
_chemical_name_systematic
;
[Bis-(2-Hydroxy-4,4-dimethyl-6-oxo-1-cyclohexenyl)]-methane
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9237(2)
_cell_length_b                   18.9167(2)
_cell_length_c                   8.72260(10)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    143
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.00
_cell_volume                     3122.46(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Siemens, 1991)'
_computing_structure_refinement  'SHELXL96 (Sheldrick, 1996b)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143
_diffrn_measurement_device       'Siemens CCD three-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'highly oriented graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_sigmaI/netI    0.015
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            40539
_diffrn_reflns_theta_max         26.47
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  540
_diffrn_standards_number         863
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   'empirical (SADABS; Sheldrick, 1996a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.162
_refine_ls_extinction_coef       0.0068(8)
_refine_ls_extinction_method     'SHELXL96 (Sheldrick, 1996b)'
_refine_ls_goodness_of_fit_all   1.062
_refine_ls_goodness_of_fit_obs   1.072
_refine_ls_hydrogen_treatment    'H atoms: see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_restrained_S_obs      1.072
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_obs          .033
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0537P)²+0.709P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.092
_refine_ls_wR_factor_obs         .091
_reflns_number_observed          3077
_reflns_number_total             3218
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ha1194.cif
_cod_data_source_block           ms3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

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

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.709P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.709P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2006826
_cod_database_fobs_code          2006826
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C1 .2500 .7500 .1921(2) .0213(4) Uani d S 1 . C
H1 .2283 .7138 .2593 .026 Uiso d R 1 . H
C11 .19170(7) .78464(7) .09970(15) .0198(3) Uani d . 1 . C
C12 .19733(8) .85886(7) .06655(17) .0223(3) Uani d . 1 . C
O12 .25218(6) .89292(6) .09864(14) .0308(3) Uani d . 1 . O
C13 .13820(8) .89644(8) -.01624(19) .0235(3) Uani d . 1 . C
H13A .1510 .9006 -.1259 .028 Uiso calc R 1 . H
H13B .1341 .9449 .0255 .028 Uiso calc R 1 . H
C14 .06546(9) .86025(9) -.00462(17) .0224(3) Uani d . 1 . C
C15 .07568(8) .78157(8) -.04274(17) .0232(3) Uani d . 1 . C
H15A .0315 .7559 -.0185 .028 Uiso calc R 1 . H
H15B .0843 .7767 -.1542 .028 Uiso calc R 1 . H
C16 .13544(7) .74778(8) .04239(16) .0211(3) Uani d . 1 . C
O16 .12907(6) .67770(5) .05336(13) .0268(3) Uani d . 1 . O
H16 .1679(14) .6587(13) .085(2) .046(6) Uiso d . 1 . H
C17 .03518(8) .86878(8) .15669(18) .0288(4) Uani d . 1 . C
H17A .0675 .8473 .2312 .043 Uiso calc R 1 . H
H17B -.0109 .8453 .1625 .043 Uiso calc R 1 . H
H17C .0296 .9192 .1799 .043 Uiso calc R 1 . H
C18 .01514(8) .89366(8) -.1213(2) .0304(3) Uani d . 1 . C
H18A .0347 .8882 -.2246 .046 Uiso calc R 1 . H
H18B .0095 .9440 -.0982 .046 Uiso calc R 1 . H
H18C -.0309 .8702 -.1157 .046 Uiso calc R 1 . H
C2 .2500 .2500 .6847(2) .0227(4) Uani d S 1 . C
H2 .2134 .2711 .7519 .027 Uiso d R 1 . H
C21 .28394(7) .30885(7) .59361(16) .0215(3) Uani d . 1 . C
C22 .35723(8) .30388(8) .55471(17) .0239(3) Uani d . 1 . C
O22 .39212(6) .24824(6) .58010(15) .0335(3) Uani d . 1 . O
C23 .39409(8) .36404(8) .4753(2) .0255(4) Uani d . 1 . C
H23A .3957 .3540 .3640 .031 Uiso calc R 1 . H
H23B .4434 .3664 .5126 .031 Uiso calc R 1 . H
C24 .35912(9) .43620(9) .49982(17) .0233(3) Uani d . 1 . C
C25 .27962(8) .42880(8) .46599(18) .0251(3) Uani d . 1 . C
H25A .2552 .4725 .4992 .030 Uiso calc R 1 . H
H25B .2729 .4241 .3539 .030 Uiso calc R 1 . H
C26 .24608(8) .36683(8) .54397(17) .0221(3) Uani d . 1 . C
O26 .17696(6) .37239(6) .56006(14) .0293(3) Uani d . 1 . O
H26 .1517(16) .3243(17) .581(3) .081(9) Uiso d . 1 . H
C27 .37060(8) .46200(8) .66484(18) .0289(4) Uani d . 1 . C
H27A .3505 .4276 .7367 .043 Uiso calc R 1 . H
H27B .3473 .5078 .6787 .043 Uiso calc R 1 . H
H27C .4213 .4670 .6845 .043 Uiso calc R 1 . H
C28 .39077(9) .49060(9) .3884(2) .0327(4) Uani d . 1 . C
H28A .3683 .5367 .4048 .049 Uiso calc R 1 . H
H28B .3825 .4752 .2826 .049 Uiso calc R 1 . H
H28C .4417 .4947 .4065 .049 Uiso calc R 1 . H
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'
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
C11 C1 C11 . 2_565 115.76(16)
C16 C11 C12 . . 118.83(13)
C16 C11 C1 . . 122.75(11)
C12 C11 C1 . . 118.38(11)
O12 C12 C11 . . 121.24(13)
O12 C12 C13 . . 118.59(13)
C11 C12 C13 . . 120.08(13)
C12 C13 C14 . . 114.93(12)
C17 C14 C18 . . 109.60(13)
C17 C14 C15 . . 110.41(12)
C18 C14 C15 . . 109.53(12)
C17 C14 C13 . . 110.41(13)
C18 C14 C13 . . 109.19(13)
C15 C14 C13 . . 107.67(13)
C16 C15 C14 . . 113.66(12)
O16 C16 C11 . . 123.41(13)
O16 C16 C15 . . 113.06(12)
C11 C16 C15 . . 123.52(13)
C21 C2 C21 2 . 116.57(16)
C26 C21 C22 . . 118.76(13)
C26 C21 C2 . . 122.00(12)
C22 C21 C2 . . 119.23(11)
O22 C22 C21 . . 121.35(14)
O22 C22 C23 . . 117.99(14)
C21 C22 C23 . . 120.60(14)
C22 C23 C24 . . 114.19(13)
C23 C24 C27 . . 110.67(14)
C23 C24 C28 . . 109.87(13)
C27 C24 C28 . . 108.97(14)
C23 C24 C25 . . 108.32(13)
C27 C24 C25 . . 110.30(13)
C28 C24 C25 . . 108.69(13)
C26 C25 C24 . . 113.49(13)
O26 C26 C21 . . 123.00(14)
O26 C26 C25 . . 113.97(13)
C21 C26 C25 . . 123.03(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 C11 . 1.5151(16) ?
C1 C11 2_565 1.5151(16) ?
C11 C16 . 1.367(2) ?
C11 C12 . 1.4374(19) ?
C12 O12 . 1.2533(18) ?
C12 C13 . 1.510(2) ?
C13 C14 . 1.541(2) ?
C14 C17 . 1.528(2) ?
C14 C18 . 1.530(2) ?
C14 C15 . 1.537(2) ?
C15 C16 . 1.496(2) ?
C16 O16 . 1.3346(19) ?
C2 C21 2 1.5108(16) ?
C2 C21 . 1.5108(16) ?
C21 C26 . 1.380(2) ?
C21 C22 . 1.431(2) ?
C22 O22 . 1.2621(19) ?
C22 C23 . 1.504(2) ?
C23 C24 . 1.532(2) ?
C24 C27 . 1.535(2) ?
C24 C28 . 1.537(2) ?
C24 C25 . 1.539(2) ?
C25 C26 . 1.497(2) ?
C26 O26 . 1.3197(19) ?
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
C11 C1 C11 C16 2_565 83.71(13)
C11 C1 C11 C12 2_565 -93.97(12)
C16 C11 C12 O12 . -170.40(14)
C1 C11 C12 O12 . 7.4(2)
C16 C11 C12 C13 . 6.2(2)
C1 C11 C12 C13 . -176.05(13)
O12 C12 C13 C14 . -160.79(14)
C11 C12 C13 C14 . 22.5(2)
C12 C13 C14 C17 . 72.20(17)
C12 C13 C14 C18 . -167.24(13)
C12 C13 C14 C15 . -48.40(17)
C17 C14 C15 C16 . -71.78(17)
C18 C14 C15 C16 . 167.44(13)
C13 C14 C15 C16 . 48.82(16)
C12 C11 C16 O16 . 172.99(13)
C1 C11 C16 O16 . -4.7(2)
C12 C11 C16 C15 . -5.3(2)
C1 C11 C16 C15 . 177.05(13)
C14 C15 C16 O16 . 157.33(12)
C14 C15 C16 C11 . -24.2(2)
C21 C2 C21 C26 2 87.20(13)
C21 C2 C21 C22 2 -91.51(12)
C26 C21 C22 O22 . -170.95(14)
C2 C21 C22 O22 . 7.8(2)
C26 C21 C22 C23 . 6.2(2)
C2 C21 C22 C23 . -175.07(13)
O22 C22 C23 C24 . -159.06(15)
C21 C22 C23 C24 . 23.7(2)
C22 C23 C24 C27 . 71.55(17)
C22 C23 C24 C28 . -168.07(14)
C22 C23 C24 C25 . -49.48(17)
C23 C24 C25 C26 . 48.53(17)
C27 C24 C25 C26 . -72.73(17)
C28 C24 C25 C26 . 167.86(13)
C22 C21 C26 O26 . 172.58(13)
C2 C21 C26 O26 . -6.1(2)
C22 C21 C26 C25 . -6.9(2)
C2 C21 C26 C25 . 174.35(13)
C24 C25 C26 O26 . 158.37(13)
C24 C25 C26 C21 . -22.1(2)
