#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/74/2237437.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_2237437
loop_
_publ_author_name
'Sorensen, Ted S.'
'Humayaun Kabir, S. M'
'Parvez, Masood'
_publ_section_title
;
 1,4,6,9-Tetra-tert-butyl-2,7-dioxatricyclo[6.3.0.0^3,6^]deca-3,8-diene
;
_journal_coeditor_code           ZL2528
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o204
_journal_paper_doi               10.1107/S1600536813000147
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C24 H40 O2'
_chemical_formula_moiety         'C24 H40 O2'
_chemical_formula_sum            'C24 H40 O2'
_chemical_formula_weight         360.56
_chemical_name_systematic
;
1,4,6,9-Tetra-tert-butyl-2,7-dioxatricyclo[6.3.0.0^3,6^]deca-3,8-diene
;
_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_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                97.209(12)
_cell_angle_beta                 96.014(13)
_cell_angle_gamma                100.703(19)
_cell_formula_units_Z            1
_cell_length_a                   5.843(2)
_cell_length_b                   9.383(3)
_cell_length_c                   10.126(4)
_cell_measurement_reflns_used    2272
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     536.5(3)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius APEXII CCD'
_diffrn_measurement_method       'ω and φ 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  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4499
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         4.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_correction_T_min  0.9865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0408
_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)+(0.0415P)²+0.1563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                1957
_reflns_number_total             2412
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2528.cif
_cod_data_source_block           I
_cod_database_code               2237437
_cod_database_fobs_code          2237437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
O O1 0.25855(13) 0.40276(8) 0.50016(8) 0.0194(2) Uani d . 1 1
C C1 0.36790(19) 0.43605(12) 0.39096(11) 0.0183(2) Uani d . 1 1
C C2 0.38127(19) 0.36693(12) 0.26899(11) 0.0195(2) Uani d . 1 1
C C3 0.6042(2) 0.47693(13) 0.25541(12) 0.0225(3) Uani d . 1 1
H H3A 0.5931 0.5253 0.1742 0.027 Uiso calc R 1 1
H H3B 0.7506 0.4384 0.2666 0.027 Uiso calc R 1 1
C C4 0.44599(19) 0.43136(12) 0.61504(11) 0.0184(2) Uani d . 1 1
C C5 0.2453(2) 0.23533(13) 0.17350(12) 0.0226(3) Uani d . 1 1
C C6 0.0667(2) 0.14183(14) 0.24394(13) 0.0304(3) Uani d . 1 1
H H6A -0.0295 0.0617 0.1785 0.037 Uiso calc R 1 1
H H6B -0.0346 0.2029 0.2839 0.037 Uiso calc R 1 1
H H6C 0.1499 0.1010 0.3146 0.037 Uiso calc R 1 1
C C7 0.4145(2) 0.14319(15) 0.11795(14) 0.0343(3) Uani d . 1 1
H H7A 0.3251 0.0586 0.0549 0.041 Uiso calc R 1 1
H H7B 0.5003 0.1089 0.1921 0.041 Uiso calc R 1 1
H H7C 0.5263 0.2032 0.0714 0.041 Uiso calc R 1 1
C C8 0.1150(2) 0.28994(15) 0.05637(13) 0.0335(3) Uani d . 1 1
H H8A 0.0317 0.2058 -0.0093 0.040 Uiso calc R 1 1
H H8B 0.2283 0.3532 0.0133 0.040 Uiso calc R 1 1
H H8C 0.0017 0.3457 0.0903 0.040 Uiso calc R 1 1
C C9 0.5229(2) 0.28551(12) 0.63873(12) 0.0219(3) Uani d . 1 1
C C10 0.7097(2) 0.30967(15) 0.76230(14) 0.0325(3) Uani d . 1 1
H H10A 0.7518 0.2159 0.7764 0.039 Uiso calc R 1 1
H H10B 0.6468 0.3501 0.8416 0.039 Uiso calc R 1 1
H H10C 0.8497 0.3785 0.7477 0.039 Uiso calc R 1 1
C C11 0.3063(2) 0.17552(14) 0.66121(14) 0.0306(3) Uani d . 1 1
H H11A 0.3515 0.0826 0.6755 0.037 Uiso calc R 1 1
H H11B 0.1872 0.1588 0.5822 0.037 Uiso calc R 1 1
H H11C 0.2418 0.2149 0.7403 0.037 Uiso calc R 1 1
C C12 0.6320(2) 0.22114(13) 0.51932(13) 0.0273(3) Uani d . 1 1
H H12A 0.6876 0.1332 0.5403 0.033 Uiso calc R 1 1
H H12B 0.7646 0.2940 0.5018 0.033 Uiso calc R 1 1
H H12C 0.5136 0.1952 0.4396 0.033 Uiso calc R 1 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 0.0016 '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
C1 O1 C4 . . 105.98(8)
C2 C1 O1 . . 136.58(10)
C2 C1 C4 . 2_666 95.84(9)
O1 C1 C4 . 2_666 127.01(10)
C1 C2 C5 . . 137.73(11)
C1 C2 C3 . . 91.75(9)
C5 C2 C3 . . 130.52(10)
C2 C3 C4 . 2_666 86.07(8)
C2 C3 H3A . . 114.3
C4 C3 H3A 2_666 . 114.3
C2 C3 H3B . . 114.3
C4 C3 H3B 2_666 . 114.3
H3A C3 H3B . . 111.5
O1 C4 C1 . 2_666 112.31(9)
O1 C4 C9 . . 109.61(9)
C1 C4 C9 2_666 . 118.82(9)
O1 C4 C3 . 2_666 115.51(9)
C1 C4 C3 2_666 2_666 84.71(8)
C9 C4 C3 . 2_666 114.21(9)
C2 C5 C6 . . 110.63(10)
C2 C5 C7 . . 109.91(10)
C6 C5 C7 . . 109.95(11)
C2 C5 C8 . . 108.22(10)
C6 C5 C8 . . 109.26(11)
C7 C5 C8 . . 108.82(11)
C5 C6 H6A . . 109.5
C5 C6 H6B . . 109.5
H6A C6 H6B . . 109.5
C5 C6 H6C . . 109.5
H6A C6 H6C . . 109.5
H6B C6 H6C . . 109.5
C5 C7 H7A . . 109.5
C5 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C5 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C5 C8 H8A . . 109.5
C5 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C5 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C11 C9 C12 . . 109.70(10)
C11 C9 C10 . . 109.15(10)
C12 C9 C10 . . 106.61(10)
C11 C9 C4 . . 108.43(10)
C12 C9 C4 . . 111.81(10)
C10 C9 C4 . . 111.11(10)
C9 C10 H10A . . 109.5
C9 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C9 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C9 C11 H11A . . 109.5
C9 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C9 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
C9 C12 H12A . . 109.5
C9 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C9 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.3744(14)
O1 C4 . 1.4733(14)
C1 C2 . 1.3380(16)
C1 C4 2_666 1.5048(15)
C2 C5 . 1.5053(16)
C2 C3 . 1.5344(16)
C3 C4 2_666 1.5615(16)
C3 H3A . 0.9900
C3 H3B . 0.9900
C4 C1 2_666 1.5048(15)
C4 C9 . 1.5557(16)
C4 C3 2_666 1.5615(16)
C5 C6 . 1.5299(17)
C5 C7 . 1.5340(17)
C5 C8 . 1.5354(18)
C6 H6A . 0.9800
C6 H6B . 0.9800
C6 H6C . 0.9800
C7 H7A . 0.9800
C7 H7B . 0.9800
C7 H7C . 0.9800
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
C9 C11 . 1.5338(17)
C9 C12 . 1.5347(17)
C9 C10 . 1.5361(18)
C10 H10A . 0.9800
C10 H10B . 0.9800
C10 H10C . 0.9800
C11 H11A . 0.9800
C11 H11B . 0.9800
C11 H11C . 0.9800
C12 H12A . 0.9800
C12 H12B . 0.9800
C12 H12C . 0.9800
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
C4 O1 C1 C2 . . 124.33(14)
C4 O1 C1 C4 . 2_666 -44.73(14)
O1 C1 C2 C5 . . 19.1(2)
C4 C1 C2 C5 2_666 . -169.70(13)
O1 C1 C2 C3 . . -161.07(13)
C4 C1 C2 C3 2_666 . 10.17(9)
C1 C2 C3 C4 . 2_666 -9.77(9)
C5 C2 C3 C4 . 2_666 170.11(12)
C1 O1 C4 C1 . 2_666 37.41(12)
C1 O1 C4 C9 . . -96.97(10)
C1 O1 C4 C3 . 2_666 132.31(10)
C1 C2 C5 C6 . . -12.26(19)
C3 C2 C5 C6 . . 167.92(11)
C1 C2 C5 C7 . . -133.88(15)
C3 C2 C5 C7 . . 46.30(16)
C1 C2 C5 C8 . . 107.40(16)
C3 C2 C5 C8 . . -72.42(15)
O1 C4 C9 C11 . . -57.21(12)
C1 C4 C9 C11 2_666 . 171.79(10)
C3 C4 C9 C11 2_666 . 74.21(12)
O1 C4 C9 C12 . . 63.86(12)
C1 C4 C9 C12 2_666 . -67.14(13)
C3 C4 C9 C12 2_666 . -164.73(9)
O1 C4 C9 C10 . . -177.16(9)
C1 C4 C9 C10 2_666 . 51.84(14)
C3 C4 C9 C10 2_666 . -45.74(13)
