#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/91/2009186.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_2009186
loop_
_publ_author_name
'Pajewski, Robert'
'Pęcak, Agnieszka'
'Ostaszewski, Ryszard'
'Jurczak, Janusz'
_publ_section_title
;
Tetracyclohexyloxaquaterene
;
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1862
_journal_page_last               1864
_journal_paper_doi               10.1107/S0108270199009099
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C40 H48 O4'
_chemical_formula_sum            'C40 H48 O4'
_chemical_formula_weight         592.78
_chemical_name_systematic
' 21,22,23,24-Tetraoxaquaterene-2,7,12,17-tetraspirocyclohexane'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.953(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.897(2)
_cell_length_b                   6.8919(5)
_cell_length_c                   21.694(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.37
_cell_measurement_theta_min      22.32
_cell_volume                     3273.4(5)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'OpenMoleN (Enraf-Nonius, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius MACH3'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            3393
_diffrn_reflns_reduction_process OpenMoleN(Enraf-Nonius,1997)
_diffrn_reflns_theta_max         74.07
_diffrn_reflns_theta_min         4.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.154
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_restrained_S_obs      1.044
_refine_ls_R_factor_all          0.067
_refine_ls_R_factor_gt           0.051
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0614P)²+2.0057P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.146
_refine_ls_wR_factor_ref         0.135
_reflns_number_gt                2636
_reflns_number_total             3303
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1288.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               2009186
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
O1 .60443(5) .17345(17) .79706(5) .0356(3) Uani d . 1 . O
C2 .62413(7) .2963(3) .75177(8) .0341(4) Uani d . 1 . C
C3 .61867(9) .4804(3) .77102(9) .0461(5) Uani d . 1 . C
H3 .6299 .5996 .7475 .055 Uiso calc R 1 . H
C4 .59383(9) .4736(3) .83140(9) .0455(5) Uani d . 1 . C
H4 .5843 .5873 .8582 .055 Uiso calc R 1 . H
C5 .58569(7) .2859(3) .84546(7) .0335(4) Uani d . 1 . C
C6 .55891(7) .1769(3) .89886(7) .0342(4) Uani d . 1 . C
C7 .60362(8) .0176(3) .92146(8) .0410(4) Uani d . 1 . C
H7A .5819 -.0697 .9541 .049 Uiso calc R 1 . H
H7B .6153 -.0710 .8841 .049 Uiso calc R 1 . H
C8 .66153(9) .1029(3) .95022(9) .0508(5) Uani d . 1 . C
H8A .6852 .1814 .9167 .061 Uiso calc R 1 . H
H8B .6900 -.0100 .9659 .061 Uiso calc R 1 . H
C9 .64665(10) .2366(4) 1.00395(9) .0590(6) Uani d . 1 . C
H9A .6269 .1549 1.0393 .071 Uiso calc R 1 . H
H9B .6872 .2980 1.0215 .071 Uiso calc R 1 . H
C10 .60305(9) .3976(4) .98449(9) .0530(5) Uani d . 1 . C
H10A .6253 .4919 .9541 .064 Uiso calc R 1 . H
H10B .5906 .4778 1.0235 .064 Uiso calc R 1 . H
C11 .54539(8) .3165(3) .95279(8) .0435(4) Uani d . 1 . C
H11A .5189 .4326 .9360 .052 Uiso calc R 1 . H
H11B .5195 .2424 .9856 .052 Uiso calc R 1 . H
C12 .50059(7) .0823(3) .87672(8) .0344(4) Uani d . 1 . C
O13 .45578(5) .20541(17) .85520(5) .0353(3) Uani d . 1 . O
C14 .40779(7) .0925(3) .83476(7) .0325(4) Uani d . 1 . C
C15 .42161(9) -.0954(3) .84371(9) .0447(5) Uani d . 1 . C
H15 .3951 -.2092 .8332 .054 Uiso calc R 1 . H
C16 .48143(9) -.1018(3) .87105(10) .0459(5) Uani d . 1 . C
H16 .5046 -.2209 .8836 .055 Uiso calc R 1 . H
C17 .35456(7) .2012(3) .80649(7) .0344(4) Uani d . 1 . C
C18 .33209(8) .3588(3) .85143(8) .0416(4) Uani d . 1 . C
H18A .3689 .4481 .8645 .050 Uiso calc R 1 . H
H18B .2993 .4457 .8289 .050 Uiso calc R 1 . H
C19 .30434(9) .2697(4) .90887(9) .0524(5) Uani d . 1 . C
H19A .2891 .3808 .9380 .063 Uiso calc R 1 . H
H19B .3379 .1899 .9330 .063 Uiso calc R 1 . H
C20 .25086(9) .1367(4) .89191(10) .0626(6) Uani d . 1 . C
H20A .2337 .0736 .9321 .075 Uiso calc R 1 . H
H20B .2157 .2190 .8713 .075 Uiso calc R 1 . H
C21 .27021(9) -.0223(3) .84785(9) .0508(5) Uani d . 1 . C
H21A .2316 -.1024 .8338 .061 Uiso calc R 1 . H
H21B .3004 -.1171 .8708 .061 Uiso calc R 1 . H
C22 .30138(8) .0608(3) .79091(8) .0419(4) Uani d . 1 . C
H22A .2687 .1347 .7639 .050 Uiso calc R 1 . H
H22B .3182 -.0544 .7645 .050 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 0.0181 0.0091 '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 0.0492 0.0322 '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 O1 C5 . . 107.50(14) yes
C3 C2 O1 . . 109.26(15) yes
C3 C2 C17 . 2_656 134.71(17) yes
O1 C2 C17 . 2_656 116.02(15) yes
C2 C3 C4 . . 106.97(17) yes
C5 C4 C3 . . 107.12(17) yes
C4 C5 O1 . . 109.14(15) yes
C4 C5 C6 . . 135.24(16) yes
O1 C5 C6 . . 115.54(15) yes
C12 C6 C5 . . 108.02(13) yes
C12 C6 C7 . . 108.85(15) no
C5 C6 C7 . . 110.21(13) no
C12 C6 C11 . . 109.79(13) no
C5 C6 C11 . . 110.68(15) no
C7 C6 C11 . . 109.27(14) no
C8 C7 C6 . . 111.99(16) no
C7 C8 C9 . . 111.07(16) no
C10 C9 C8 . . 111.73(15) no
C9 C10 C11 . . 111.53(19) no
C10 C11 C6 . . 113.55(15) no
C16 C12 O13 . . 109.43(15) yes
C16 C12 C6 . . 134.53(16) yes
O13 C12 C6 . . 116.02(15) yes
C12 O13 C14 . . 107.34(13) yes
C15 C14 O13 . . 109.26(15) yes
C15 C14 C17 . . 135.15(16) yes
O13 C14 C17 . . 115.56(15) yes
C14 C15 C16 . . 107.01(16) yes
C12 C16 C15 . . 106.97(17) yes
C2 C17 C14 2_656 . 108.04(13) yes
C2 C17 C18 2_656 . 109.31(15) no
C14 C17 C18 . . 110.17(13) no
C2 C17 C22 2_656 . 109.36(13) no
C14 C17 C22 . . 110.61(15) no
C18 C17 C22 . . 109.32(14) no
C19 C18 C17 . . 111.61(17) no
C18 C19 C20 . . 111.05(16) no
C21 C20 C19 . . 111.33(16) no
C20 C21 C22 . . 111.72(19) no
C21 C22 C17 . . 113.67(14) no
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
O1 C2 . 1.372(2) yes
O1 C5 . 1.373(2) yes
C2 C3 . 1.342(2) yes
C2 C17 2_656 1.505(2) yes
C3 C4 . 1.427(3) yes
C4 C5 . 1.341(2) yes
C5 C6 . 1.508(2) yes
C6 C12 . 1.505(2) yes
C6 C7 . 1.546(2) no
C6 C11 . 1.547(2) no
C7 C8 . 1.522(2) no
C8 C9 . 1.525(3) no
C9 C10 . 1.519(3) no
C10 C11 . 1.533(2) no
C12 C16 . 1.341(2) yes
C12 O13 . 1.373(2) yes
O13 C14 . 1.375(2) yes
C14 C15 . 1.343(2) yes
C14 C17 . 1.507(2) yes
C15 C16 . 1.429(2) yes
C17 C2 2_656 1.505(2) yes
C17 C18 . 1.545(2) no
C17 C22 . 1.547(2) no
C18 C19 . 1.525(3) no
C19 C20 . 1.528(3) no
C20 C21 . 1.519(3) no
C21 C22 . 1.532(2) 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_4
_geom_torsion
_geom_torsion_publ_flag
C5 O1 C2 C3 . . 0.61(18) no
C5 O1 C2 C17 . 2_656 -178.61(13) no
O1 C2 C3 C4 . . -0.4(2) no
C17 C2 C3 C4 2_656 . 178.57(17) no
C2 C3 C4 C5 . . 0.1(2) no
C3 C4 C5 O1 . . 0.3(2) no
C3 C4 C5 C6 . . -176.19(17) no
C2 O1 C5 C4 . . -0.54(18) no
C2 O1 C5 C6 . . 176.70(13) no
C4 C5 C6 C12 . . 111.0(2) no
O1 C5 C6 C12 . . -65.26(17) no
C4 C5 C6 C7 . . -130.1(2) no
O1 C5 C6 C7 . . 53.55(18) no
C4 C5 C6 C11 . . -9.2(3) no
O1 C5 C6 C11 . . 174.53(13) no
C12 C6 C7 C8 . . -174.64(14) no
C5 C6 C7 C8 . . 67.07(18) no
C11 C6 C7 C8 . . -54.75(19) no
C6 C7 C8 C9 . . 57.6(2) no
C7 C8 C9 C10 . . -56.4(3) no
C8 C9 C10 C11 . . 53.5(2) no
C9 C10 C11 C6 . . -52.6(2) no
C12 C6 C11 C10 . . 171.76(17) no
C5 C6 C11 C10 . . -69.1(2) no
C7 C6 C11 C10 . . 52.5(2) no
C5 C6 C12 C16 . . 117.1(2) no
C7 C6 C12 C16 . . -2.5(3) no
C11 C6 C12 C16 . . -122.1(2) no
C5 C6 C12 O13 . . -60.57(18) no
C7 C6 C12 O13 . . 179.76(13) no
C11 C6 C12 O13 . . 60.20(19) no
C16 C12 O13 C14 . . -0.92(19) no
C6 C12 O13 C14 . . 177.34(13) no
C12 O13 C14 C15 . . 0.65(19) no
C12 O13 C14 C17 . . -177.39(13) no
O13 C14 C15 C16 . . -0.2(2) no
C17 C14 C15 C16 . . 177.34(18) no
O13 C12 C16 C15 . . 0.8(2) no
C6 C12 C16 C15 . . -176.99(18) no
C14 C15 C16 C12 . . -0.4(2) no
C15 C14 C17 C2 . 2_656 -111.8(2) no
O13 C14 C17 C2 . 2_656 65.55(17) no
C15 C14 C17 C18 . . 128.8(2) no
O13 C14 C17 C18 . . -53.80(18) no
C15 C14 C17 C22 . . 7.9(3) no
O13 C14 C17 C22 . . -174.78(13) no
C2 C17 C18 C19 2_656 . 174.62(14) no
C14 C17 C18 C19 . . -66.80(18) no
C22 C17 C18 C19 . . 54.94(19) no
C17 C18 C19 C20 . . -58.4(2) no
C18 C19 C20 C21 . . 57.0(3) no
C19 C20 C21 C22 . . -53.5(2) no
C20 C21 C22 C17 . . 52.3(2) no
C2 C17 C22 C21 2_656 . -171.87(16) no
C14 C17 C22 C21 . . 69.3(2) no
C18 C17 C22 C21 . . -52.2(2) no
