#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/62/2236285.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_2236285
loop_
_publ_author_name
'Lough, Alan J.'
'Jack, Kelsey'
'Tam, William'
_publ_section_title
;
 Hexamethyl
 13,14-dioxapentacyclo[8.2.1.1^4,7^.0^2,9^.0^3,8^]tetradeca-5,11-diene-1,4,5,6,11,12-hexacarboxylate
;
_journal_coeditor_code           HB6954
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2963
_journal_paper_doi               10.1107/S1600536812039232
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C24 H24 O14'
_chemical_formula_moiety         'C24 H24 O14'
_chemical_formula_sum            'C24 H24 O14'
_chemical_formula_weight         536.43
_chemical_name_systematic
;
Hexamethyl
13,14-dioxapentacyclo[8.2.1.1^4,7^.0^2,9^.0^3,8^]tetradeca-
5,11-diene-1,4,5,6,11,12-hexacarboxylate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.430(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.1309(18)
_cell_length_b                   10.0840(7)
_cell_length_c                   9.5922(7)
_cell_measurement_reflns_used    6078
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.99
_cell_volume                     2419.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Bruker Triumph'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11038
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0518P)²+1.6228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                2366
_reflns_number_total             2787
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6954.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236285
_cod_database_fobs_code          2236285
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_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 0.92545(3) 0.44122(8) 0.38295(8) 0.01527(19) Uani d . 1 1
O O2 0.91010(5) 0.09784(10) 0.30367(10) 0.0322(3) Uani d . 1 1
O O3 0.94389(4) 0.20695(9) 0.49626(9) 0.0237(2) Uani d . 1 1
O O4 0.80179(4) 0.21560(10) 0.15093(10) 0.0272(2) Uani d . 1 1
O O5 0.85951(3) 0.23192(9) -0.01412(9) 0.0206(2) Uani d . 1 1
O O6 0.84027(4) 0.69996(9) 0.08929(10) 0.0250(2) Uani d . 1 1
O O7 0.80331(4) 0.50766(9) 0.00853(10) 0.0227(2) Uani d . 1 1
C C1 0.97293(4) 0.35610(11) 0.20451(11) 0.0133(2) Uani d . 1 1
H H1 0.9723 0.3106 0.1117 0.016 Uiso calc R 1 1
C C2 0.92422(4) 0.33021(12) 0.28941(11) 0.0141(2) Uani d . 1 1
C C3 0.87579(4) 0.36255(12) 0.18620(11) 0.0149(2) Uani d . 1 1
C C4 0.87513(5) 0.49467(12) 0.17852(12) 0.0157(2) Uani d . 1 1
C C5 0.92285(4) 0.54296(12) 0.27571(11) 0.0149(2) Uani d . 1 1
H H5A 0.9202 0.6361 0.3103 0.018 Uiso calc R 1 1
C C6 0.97323(4) 0.51140(11) 0.20141(11) 0.0134(2) Uani d . 1 1
H H6 0.9748 0.5528 0.1071 0.016 Uiso calc R 1 1
C C7 0.92448(5) 0.19809(12) 0.36304(12) 0.0171(3) Uani d . 1 1
C C8 0.93932(6) 0.08885(15) 0.58051(15) 0.0322(3) Uani d . 1 1
H H8A 0.9590 0.1018 0.6726 0.048 Uiso calc R 1 1
H H8B 0.9543 0.0129 0.5338 0.048 Uiso calc R 1 1
H H8C 0.9016 0.0721 0.5920 0.048 Uiso calc R 1 1
C C9 0.84091(5) 0.26211(12) 0.10758(12) 0.0165(2) Uani d . 1 1
C C10 0.82628(5) 0.14106(15) -0.10214(14) 0.0263(3) Uani d . 1 1
H H10A 0.8400 0.1345 -0.1942 0.039 Uiso calc R 1 1
H H10B 0.7895 0.1742 -0.1134 0.039 Uiso calc R 1 1
H H10C 0.8270 0.0533 -0.0582 0.039 Uiso calc R 1 1
C C11 0.83860(4) 0.58061(13) 0.08826(12) 0.0170(2) Uani d . 1 1
C C12 0.76407(5) 0.58064(14) -0.08202(15) 0.0266(3) Uani d . 1 1
H H12A 0.7429 0.5185 -0.1433 0.040 Uiso calc R 1 1
H H12B 0.7824 0.6433 -0.1392 0.040 Uiso calc R 1 1
H H12C 0.7404 0.6294 -0.0247 0.040 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
C2 O1 C5 . . 96.42(8)
C7 O3 C8 . . 116.11(11)
C9 O5 C10 . . 114.99(10)
C11 O7 C12 . . 116.12(10)
C1 C1 C2 2_755 . 113.51(11)
C1 C1 C6 2_755 . 90.30(5)
C2 C1 C6 . . 100.56(9)
C1 C1 H1 2_755 . 116.2
C2 C1 H1 . . 116.2
C6 C1 H1 . . 116.2
O1 C2 C7 . . 113.46(9)
O1 C2 C3 . . 101.97(9)
C7 C2 C3 . . 117.36(10)
O1 C2 C1 . . 103.01(9)
C7 C2 C1 . . 115.14(9)
C3 C2 C1 . . 104.05(9)
C4 C3 C9 . . 130.13(11)
C4 C3 C2 . . 104.70(10)
C9 C3 C2 . . 125.05(10)
C3 C4 C11 . . 128.35(11)
C3 C4 C5 . . 106.24(10)
C11 C4 C5 . . 125.29(11)
O1 C5 C4 . . 100.80(9)
O1 C5 C6 . . 101.41(9)
C4 C5 C6 . . 106.46(9)
O1 C5 H5A . . 115.4
C4 C5 H5A . . 115.4
C6 C5 H5A . . 115.4
C5 C6 C6 . 2_755 114.97(11)
C5 C6 C1 . . 101.06(9)
C6 C6 C1 2_755 . 89.66(5)
C5 C6 H6 . . 115.8
C6 C6 H6 2_755 . 115.8
C1 C6 H6 . . 115.8
O2 C7 O3 . . 125.51(12)
O2 C7 C2 . . 122.33(11)
O3 C7 C2 . . 112.12(10)
O3 C8 H8A . . 109.5
O3 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
O3 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
O4 C9 O5 . . 125.55(11)
O4 C9 C3 . . 123.42(11)
O5 C9 C3 . . 111.03(10)
O5 C10 H10A . . 109.5
O5 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
O5 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
O6 C11 O7 . . 125.15(11)
O6 C11 C4 . . 124.12(11)
O7 C11 C4 . . 110.72(11)
O7 C12 H12A . . 109.5
O7 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
O7 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 C2 . 1.4331(14)
O1 C5 . 1.4500(14)
O2 C7 . 1.1991(16)
O3 C7 . 1.3271(15)
O3 C8 . 1.4499(16)
O4 C9 . 1.1987(15)
O5 C9 . 1.3331(15)
O5 C10 . 1.4547(15)
O6 C11 . 1.2043(16)
O7 C11 . 1.3358(15)
O7 C12 . 1.4514(14)
C1 C1 2_755 1.545(2)
C1 C2 . 1.5553(15)
C1 C6 . 1.5663(16)
C1 H1 . 1.0000
C2 C7 . 1.5076(16)
C2 C3 . 1.5295(15)
C3 C4 . 1.3343(17)
C3 C9 . 1.4960(16)
C4 C11 . 1.4808(16)
C4 C5 . 1.5275(15)
C5 C6 . 1.5435(16)
C5 H5A . 1.0000
C6 C6 2_755 1.563(2)
C6 H6 . 1.0000
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
C10 H10A . 0.9800
C10 H10B . 0.9800
C10 H10C . 0.9800
C12 H12A . 0.9800
C12 H12B . 0.9800
C12 H12C . 0.9800
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
C6 H6 O1 6_565 1.00 2.38 3.2105(13) 140 yes
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
C5 O1 C2 C7 . . -178.09(9)
C5 O1 C2 C3 . . -50.92(9)
C5 O1 C2 C1 . . 56.76(9)
C1 C1 C2 O1 2_755 . 62.75(8)
C6 C1 C2 O1 . . -32.23(10)
C1 C1 C2 C7 2_755 . -61.30(10)
C6 C1 C2 C7 . . -156.28(9)
C1 C1 C2 C3 2_755 . 168.84(6)
C6 C1 C2 C3 . . 73.86(10)
O1 C2 C3 C4 . . 32.45(11)
C7 C2 C3 C4 . . 157.06(10)
C1 C2 C3 C4 . . -74.43(11)
O1 C2 C3 C9 . . -151.28(10)
C7 C2 C3 C9 . . -26.67(16)
C1 C2 C3 C9 . . 101.85(12)
C9 C3 C4 C11 . . 0.3(2)
C2 C3 C4 C11 . . 176.35(11)
C9 C3 C4 C5 . . -175.80(11)
C2 C3 C4 C5 . . 0.21(12)
C2 O1 C5 C4 . . 50.47(9)
C2 O1 C5 C6 . . -58.97(9)
C3 C4 C5 O1 . . -32.25(12)
C11 C4 C5 O1 . . 151.47(11)
C3 C4 C5 C6 . . 73.20(12)
C11 C4 C5 C6 . . -103.08(12)
O1 C5 C6 C6 . 2_755 -56.92(8)
C4 C5 C6 C6 . 2_755 -161.93(7)
O1 C5 C6 C1 . . 37.92(10)
C4 C5 C6 C1 . . -67.09(10)
C1 C1 C6 C5 2_755 . -117.62(10)
C2 C1 C6 C5 . . -3.62(10)
C1 C1 C6 C6 2_755 2_755 -2.22(12)
C2 C1 C6 C6 . 2_755 111.78(10)
C8 O3 C7 O2 . . -10.06(19)
C8 O3 C7 C2 . . 172.22(11)
O1 C2 C7 O2 . . 160.49(12)
C3 C2 C7 O2 . . 41.86(17)
C1 C2 C7 O2 . . -81.16(15)
O1 C2 C7 O3 . . -21.71(14)
C3 C2 C7 O3 . . -140.34(10)
C1 C2 C7 O3 . . 96.65(12)
C10 O5 C9 O4 . . 4.24(18)
C10 O5 C9 C3 . . -176.27(10)
C4 C3 C9 O4 . . -94.36(17)
C2 C3 C9 O4 . . 90.36(16)
C4 C3 C9 O5 . . 86.14(16)
C2 C3 C9 O5 . . -89.15(13)
C12 O7 C11 O6 . . -0.57(18)
C12 O7 C11 C4 . . 178.21(10)
C3 C4 C11 O6 . . 178.87(13)
C5 C4 C11 O6 . . -5.68(19)
C3 C4 C11 O7 . . 0.08(18)
C5 C4 C11 O7 . . 175.53(11)
