#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/01/2200165.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_2200165
loop_
_publ_author_name
'Parvez, Masood'
'Simion, Dan V.'
'Sorensen, Ted S.'
_publ_section_title
;
 A novel chiral C₂ axially symmetric acenaphthoquinone diketal
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o366
_journal_page_last               o367
_journal_paper_doi               10.1107/S1600536801005049
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C20 H22 O4'
_chemical_formula_moiety         'C20 H22 O4'
_chemical_formula_sum            'C20 H22 O4'
_chemical_formula_weight         326.38
_chemical_name_common            'bis Dioxane'
_chemical_name_systematic
;
(-)-(4R,5R,4''R,5''R)-4,5,4'',5''-Tetramethyldispiro[1,3-dioxalane-
2,1'(2'H)-acenaphthylene-2',2''-1,3-dioxalane]
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.799(3)
_cell_length_b                   19.331(5)
_cell_length_c                   9.054(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      10.0
_cell_volume                     1715.0(9)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1994)'
_computing_molecular_graphics    TEXSAN
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 1997)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Rigaku AFC-6S'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .00
_diffrn_reflns_av_sigmaI/netI    .12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1758
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        <0.5
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .09
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             696
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .21
_exptl_crystal_size_min          .13
_refine_diff_density_max         .22
_refine_diff_density_min         -.24
_refine_ls_abs_structure_details '(Flack, 1983)'
_refine_ls_abs_structure_Flack   -1(4)
_refine_ls_extinction_coef       .013(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.00
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.00
_refine_ls_R_factor_all          .154
_refine_ls_R_factor_gt           .040
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0835P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .167
_reflns_number_gt                831
_reflns_number_total             1758
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6011.cif
_cod_data_source_block           I
_cod_depositor_comments
;
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 
;
_cod_database_code               2200165
_cod_database_fobs_code          2200165
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .4224(4) .8113(2) .1498(5) .0382(11) Uani d . 1 . . O
O2 .2437(4) .7621(2) .0262(4) .0382(12) Uani d . 1 . . O
O3 .2818(5) .8308(2) .3954(4) .0396(12) Uani d . 1 . . O
O4 .0994(4) .8184(2) .2423(4) .0368(11) Uani d . 1 . . O
C1 .2786(6) .6664(3) .3185(6) .0330(15) Uani d . 1 . . C
C2 .1912(7) .7163(3) .3759(6) .0343(16) Uani d . 1 . . C
C3 .1042(7) .6992(3) .4889(7) .0417(17) Uani d . 1 . . C
H3 .0432 .7322 .5269 .050 Uiso calc R 1 . . H
C4 .1073(8) .6331(4) .5462(7) .052(2) Uani d . 1 . . C
H4 .0482 .6219 .6244 .062 Uiso calc R 1 . . H
C5 .1956(7) .5822(4) .4917(7) .0476(19) Uani d . 1 . . C
H5 .1958 .5377 .5334 .057 Uiso calc R 1 . . H
C6 .2844(7) .5981(3) .3737(7) .0394(17) Uani d . 1 . . C
C7 .3782(7) .5544(3) .3019(8) .0457(18) Uani d . 1 . . C
H7 .3869 .5082 .3332 .055 Uiso calc R 1 . . H
C8 .4574(7) .5777(3) .1869(8) .048(2) Uani d . 1 . . C
H8 .5202 .5473 .1430 .058 Uiso calc R 1 . . H
C9 .4475(7) .6451(4) .1335(7) .0425(18) Uani d . 1 . . C
H9 .5016 .6594 .0534 .051 Uiso calc R 1 . . H
C10 .3567(5) .6912(3) .1997(7) .0308(15) Uani d . 1 . . C
C11 .3138(6) .7633(3) .1641(6) .0354(16) Uani d . 1 . . C
C12 .2172(6) .7847(3) .2969(6) .0302(14) Uani d . 1 . . C
C13 .4487(6) .8185(3) -.0069(7) .0368(16) Uani d . 1 . . C
H13 .5049 .7790 -.0405 .044 Uiso calc R 1 . . H
C14 .3072(6) .8118(4) -.0709(6) .0384(16) Uani d . 1 . . C
H14 .2594 .8567 -.0614 .046 Uiso calc R 1 . . H
C15 .5246(7) .8837(3) -.0339(8) .059(2) Uani d . 1 . . C
H15A .6136 .8809 .0125 .088 Uiso calc R 1 . . H
H15B .4740 .9222 .0075 .088 Uiso calc R 1 . . H
H15C .5356 .8904 -.1394 .088 Uiso calc R 1 . . H
C16 .2968(8) .7876(4) -.2260(6) .066(2) Uani d . 1 . . C
H16A .2016 .7858 -.2550 .099 Uiso calc R 1 . . H
H16B .3367 .7418 -.2343 .099 Uiso calc R 1 . . H
H16C .3454 .8193 -.2901 .099 Uiso calc R 1 . . H
C17 .2239(7) .8971(3) .3690(7) .0408(17) Uani d . 1 . . C
H17 .2700 .9188 .2834 .049 Uiso calc R 1 . . H
C18 .0793(7) .8804(3) .3288(8) .0438(18) Uani d . 1 . . C
H18 .0271 .8691 .4192 .053 Uiso calc R 1 . . H
C19 .2438(7) .9423(4) .5052(7) .057(2) Uani d . 1 . . C
H19A .3405 .9502 .5208 .085 Uiso calc R 1 . . H
H19B .2056 .9191 .5908 .085 Uiso calc R 1 . . H
H19C .1980 .9862 .4908 .085 Uiso calc R 1 . . H
C20 .0015(8) .9315(3) .2383(9) .059(2) Uani d . 1 . . C
H20A -.0899 .9141 .2204 .088 Uiso calc R 1 . . H
H20B .0476 .9385 .1447 .088 Uiso calc R 1 . . H
H20C -.0039 .9751 .2910 .088 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
_geom_angle_publ_flag
C11 O1 C13 106.6(5) n
C11 O2 C14 108.4(4) n
C12 O3 C17 106.5(5) n
C12 O4 C18 107.8(4) n
C2 C1 C10 112.6(6) n
C2 C1 C6 122.7(6) n
C10 C1 C6 124.6(6) n
C3 C2 C1 119.6(6) n
C3 C2 C12 131.5(6) n
C1 C2 C12 108.9(5) n
C2 C3 C4 119.4(6) n
C2 C3 H3 120.3 n
C4 C3 H3 120.3 n
C3 C4 C5 122.1(7) n
C3 C4 H4 118.9 n
C5 C4 H4 118.9 n
C4 C5 C6 119.7(6) n
C4 C5 H5 120.2 n
C6 C5 H5 120.2 n
C7 C6 C5 128.5(6) n
C7 C6 C1 115.1(6) n
C5 C6 C1 116.5(6) n
C8 C7 C6 121.4(6) n
C8 C7 H7 119.3 n
C6 C7 H7 119.3 n
C7 C8 C9 122.1(7) n
C7 C8 H8 119.0 n
C9 C8 H8 119.0 n
C8 C9 C10 119.5(6) n
C8 C9 H9 120.2 n
C10 C9 H9 120.2 n
C9 C10 C1 117.3(6) n
C9 C10 C11 133.2(6) n
C1 C10 C11 109.3(5) n
O1 C11 O2 107.0(4) n
O1 C11 C10 114.8(5) n
O2 C11 C10 108.0(5) n
O1 C11 C12 110.3(5) n
O2 C11 C12 112.4(5) n
C10 C11 C12 104.3(5) n
O3 C12 O4 107.2(4) n
O3 C12 C2 109.0(5) n
O4 C12 C2 115.3(5) n
O3 C12 C11 112.1(5) n
O4 C12 C11 110.0(4) n
C2 C12 C11 103.3(5) n
O1 C13 C15 109.4(5) n
O1 C13 C14 101.8(5) n
C15 C13 C14 118.1(6) n
O1 C13 H13 109.1 n
C15 C13 H13 109.1 n
C14 C13 H13 109.1 n
O2 C14 C16 109.7(6) n
O2 C14 C13 102.7(5) n
C16 C14 C13 117.0(6) n
O2 C14 H14 109.0 n
C16 C14 H14 109.0 n
C13 C14 H14 109.0 n
C13 C15 H15A 109.5 n
C13 C15 H15B 109.5 n
H15A C15 H15B 109.5 n
C13 C15 H15C 109.5 n
H15A C15 H15C 109.5 n
H15B C15 H15C 109.5 n
C14 C16 H16A 109.5 n
C14 C16 H16B 109.5 n
H16A C16 H16B 109.5 n
C14 C16 H16C 109.5 n
H16A C16 H16C 109.5 n
H16B C16 H16C 109.5 n
O3 C17 C18 102.9(5) n
O3 C17 C19 109.2(5) n
C18 C17 C19 116.2(6) n
O3 C17 H17 109.4 n
C18 C17 H17 109.4 n
C19 C17 H17 109.4 n
O4 C18 C20 108.7(5) n
O4 C18 C17 100.4(5) n
C20 C18 C17 118.3(6) n
O4 C18 H18 109.6 n
C20 C18 H18 109.6 n
C17 C18 H18 109.6 n
C17 C19 H19A 109.5 n
C17 C19 H19B 109.5 n
H19A C19 H19B 109.5 n
C17 C19 H19C 109.5 n
H19A C19 H19C 109.5 n
H19B C19 H19C 109.5 n
C18 C20 H20A 109.5 n
C18 C20 H20B 109.5 n
H20A C20 H20B 109.5 n
C18 C20 H20C 109.5 n
H20A C20 H20C 109.5 n
H20B C20 H20C 109.5 n
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 C11 . 1.418(7) n
O1 C13 . 1.449(7) n
O2 C11 . 1.425(7) n
O2 C14 . 1.443(7) n
O3 C12 . 1.411(7) n
O3 C17 . 1.423(7) n
O4 C12 . 1.415(7) n
O4 C18 . 1.444(7) n
C1 C2 . 1.391(8) n
C1 C10 . 1.405(8) n
C1 C6 . 1.413(8) n
C2 C3 . 1.371(8) n
C2 C12 . 1.525(8) n
C3 C4 . 1.379(9) n
C3 H3 . .9400 n
C4 C5 . 1.400(10) n
C4 H4 . .9400 n
C5 C6 . 1.411(9) n
C5 H5 . .9400 n
C6 C7 . 1.408(9) n
C7 C8 . 1.374(9) n
C7 H7 . .9400 n
C8 C9 . 1.392(9) n
C8 H8 . .9400 n
C9 C10 . 1.395(8) n
C9 H9 . .9400 n
C10 C11 . 1.492(9) n
C11 C12 . 1.585(8) n
C13 C15 . 1.482(8) n
C13 C14 . 1.508(9) n
C13 H13 . .9900 n
C14 C16 . 1.483(8) n
C14 H14 . .9900 n
C15 H15A . .9700 n
C15 H15B . .9700 n
C15 H15C . .9700 n
C16 H16A . .9700 n
C16 H16B . .9700 n
C16 H16C . .9700 n
C17 C18 . 1.499(9) n
C17 C19 . 1.524(8) n
C17 H17 . .9900 n
C18 C20 . 1.493(9) n
C18 H18 . .9900 n
C19 H19A . .9700 n
C19 H19B . .9700 n
C19 H19C . .9700 n
C20 H20A . .9700 n
C20 H20B . .9700 n
C20 H20C . .9700 n
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
_geom_torsion_publ_flag
C10 C1 C2 C3 177.5(5) n
C6 C1 C2 C3 -1.3(9) n
C10 C1 C2 C12 -4.4(7) n
C6 C1 C2 C12 176.8(5) n
C1 C2 C3 C4 1.5(9) n
C12 C2 C3 C4 -176.1(6) n
C2 C3 C4 C5 -.7(10) n
C3 C4 C5 C6 -.4(10) n
C4 C5 C6 C7 -178.7(7) n
C4 C5 C6 C1 .7(9) n
C2 C1 C6 C7 179.7(6) n
C10 C1 C6 C7 1.0(9) n
C2 C1 C6 C5 .2(9) n
C10 C1 C6 C5 -178.5(5) n
C5 C6 C7 C8 179.5(7) n
C1 C6 C7 C8 .1(9) n
C6 C7 C8 C9 -1.3(10) n
C7 C8 C9 C10 1.3(10) n
C8 C9 C10 C1 -.3(9) n
C8 C9 C10 C11 -174.6(6) n
C2 C1 C10 C9 -179.7(5) n
C6 C1 C10 C9 -.9(8) n
C2 C1 C10 C11 -4.1(7) n
C6 C1 C10 C11 174.7(5) n
C13 O1 C11 O2 -21.3(6) n
C13 O1 C11 C10 98.6(5) n
C13 O1 C11 C12 -143.8(5) n
C14 O2 C11 O1 -2.1(6) n
C14 O2 C11 C10 -126.3(5) n
C14 O2 C11 C12 119.1(5) n
C9 C10 C11 O1 -54.2(9) n
C1 C10 C11 O1 131.1(5) n
C9 C10 C11 O2 65.1(8) n
C1 C10 C11 O2 -109.5(5) n
C9 C10 C11 C12 -175.1(6) n
C1 C10 C11 C12 10.3(6) n
C17 O3 C12 O4 -15.2(6) n
C17 O3 C12 C2 -140.7(5) n
C17 O3 C12 C11 105.5(6) n
C18 O4 C12 O3 -10.4(6) n
C18 O4 C12 C2 111.2(5) n
C18 O4 C12 C11 -132.5(5) n
C3 C2 C12 O3 68.7(8) n
C1 C2 C12 O3 -109.1(5) n
C3 C2 C12 O4 -51.8(9) n
C1 C2 C12 O4 130.3(5) n
C3 C2 C12 C11 -171.9(6) n
C1 C2 C12 C11 10.3(6) n
O1 C11 C12 O3 -18.7(7) n
O2 C11 C12 O3 -138.0(5) n
C10 C11 C12 O3 105.1(5) n
O1 C11 C12 O4 100.4(5) n
O2 C11 C12 O4 -19.0(7) n
C10 C11 C12 O4 -135.8(5) n
O1 C11 C12 C2 -135.9(5) n
O2 C11 C12 C2 104.7(6) n
C10 C11 C12 C2 -12.1(6) n
C11 O1 C13 C15 160.5(5) n
C11 O1 C13 C14 34.9(6) n
C11 O2 C14 C16 148.4(6) n
C11 O2 C14 C13 23.3(6) n
O1 C13 C14 O2 -35.0(6) n
C15 C13 C14 O2 -154.7(6) n
O1 C13 C14 C16 -155.2(6) n
C15 C13 C14 C16 85.1(8) n
C12 O3 C17 C18 33.7(6) n
C12 O3 C17 C19 157.7(5) n
C12 O4 C18 C20 154.8(5) n
C12 O4 C18 C17 29.9(6) n
O3 C17 C18 O4 -38.4(6) n
C19 C17 C18 O4 -157.6(5) n
O3 C17 C18 C20 -156.4(6) n
C19 C17 C18 C20 84.3(8) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24731066
