#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/64/2226448.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_2226448
loop_
_publ_author_name
'Grubba, Rafał'
'Ponikiewski, Łukasz'
'Pikies, Jerzy'
_publ_section_title
;
 Dispiro[cyclopropane-1,5'-endo-tricyclo[5.2.1.0^2,6^]deca-3,8-diene-10',1''-cyclopropane]
;
_journal_coeditor_code           GK2280
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1648
_journal_paper_doi               10.1107/S1600536810021951
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H16'
_chemical_formula_moiety         'C14 H16'
_chemical_formula_sum            'C14 H16'
_chemical_formula_weight         184.27
_chemical_name_systematic
;
Dispiro[cyclopropane-1,5'-endo-tricyclo[5.2.1.0^2,6^]deca-3,8-diene-
10',1''-cyclopropane]
;
_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
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                68.488(9)
_cell_angle_beta                 81.625(7)
_cell_angle_gamma                73.351(8)
_cell_formula_units_Z            2
_cell_length_a                   6.4079(5)
_cell_length_b                   8.6355(8)
_cell_length_c                   10.7216(10)
_cell_measurement_reflns_used    1384
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4867
_cell_measurement_theta_min      2.6128
_cell_volume                     528.27(9)
_computing_cell_refinement
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.1883
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3444
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.77535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0950P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1683
_reflns_number_gt                1348
_reflns_number_total             2269
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2280.cif
_cod_data_source_block           I
_cod_original_cell_volume        528.27(8)
_cod_database_code               2226448
_cod_database_fobs_code          2226448
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_disorder_assembly
_atom_site_disorder_group
C C1 0.7397(3) 0.6967(3) 0.2398(2) 0.0523(6) Uani d . 1 . .
H H1A 0.7789 0.7846 0.2623 0.063 Uiso calc R 1 . .
C C2 0.7772(3) 0.5136(3) 0.35036(19) 0.0469(5) Uani d . 1 . .
H H2A 0.7291 0.522 0.4392 0.056 Uiso calc R 1 . .
C C3 0.9992(3) 0.3926(3) 0.3543(2) 0.0577(6) Uani d . 1 . .
H H3A 1.1234 0.4104 0.3763 0.069 Uiso calc R 1 . .
C C4 0.9994(3) 0.2591(3) 0.3232(2) 0.0539(6) Uani d . 1 . .
H H4A 1.1241 0.1731 0.3191 0.065 Uiso calc R 1 . .
C C5 0.7809(3) 0.2602(2) 0.29543(19) 0.0441(5) Uani d . 1 . .
C C6 0.6293(3) 0.4281(2) 0.30671(18) 0.0398(5) Uani d . 1 . .
H H6A 0.5122 0.4035 0.3749 0.048 Uiso calc R 1 . .
C C7 0.5333(3) 0.5718(2) 0.17594(18) 0.0451(5) Uani d . 1 . .
H H7A 0.4042 0.5598 0.145 0.054 Uiso calc R 1 . .
C C8 0.7187(4) 0.5983(3) 0.0741(2) 0.0559(6) Uani d . 1 . .
H H8A 0.7437 0.5677 -0.0024 0.067 Uiso calc R 1 . .
C C9 0.8395(3) 0.6717(3) 0.1112(2) 0.0594(6) Uani d . 1 . .
H H9A 0.9646 0.7027 0.0658 0.071 Uiso calc R 1 . .
C C10 0.5010(3) 0.7287(2) 0.21729(19) 0.0455(5) Uani d . 1 . .
C C11 0.3131(4) 0.7909(3) 0.3016(2) 0.0631(6) Uani d . 1 . .
H H11A 0.3434 0.8275 0.371 0.076 Uiso calc R 1 . .
H H11B 0.1933 0.7363 0.3235 0.076 Uiso calc R 1 . .
C C12 0.3480(4) 0.8997(3) 0.1568(2) 0.0646(6) Uani d . 1 . .
H H12A 0.2489 0.9102 0.0921 0.078 Uiso calc R 1 . .
H H12B 0.399 1.0014 0.1396 0.078 Uiso calc R 1 . .
C C13 0.7460(4) 0.1787(3) 0.2006(2) 0.0620(6) Uani d . 1 . .
H H13A 0.6199 0.2352 0.1456 0.074 Uiso calc R 1 . .
H H13B 0.874 0.1232 0.1577 0.074 Uiso calc R 1 . .
C C14 0.7068(4) 0.0959(3) 0.3469(2) 0.0644(6) Uani d . 1 . .
H H14B 0.8112 -0.0099 0.393 0.077 Uiso calc R 1 . .
H H14C 0.5569 0.1022 0.3809 0.077 Uiso calc R 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 0 '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
C9 C1 C10 . . 100.07(16) ?
C9 C1 C2 . . 106.78(17) ?
C10 C1 C2 . . 99.49(14) ?
C9 C1 H1A . . 116 ?
C10 C1 H1A . . 116 ?
C2 C1 H1A . . 116 ?
C3 C2 C6 . . 103.53(15) ?
C3 C2 C1 . . 117.77(17) ?
C6 C2 C1 . . 102.59(14) ?
C3 C2 H2A . . 110.8 ?
C6 C2 H2A . . 110.8 ?
C1 C2 H2A . . 110.8 ?
C4 C3 C2 . . 112.80(18) ?
C4 C3 H3A . . 123.6 ?
C2 C3 H3A . . 123.6 ?
C3 C4 C5 . . 112.61(19) ?
C3 C4 H4A . . 123.7 ?
C5 C4 H4A . . 123.7 ?
C4 C5 C13 . . 122.29(18) ?
C4 C5 C14 . . 120.29(18) ?
C13 C5 C14 . . 58.99(13) ?
C4 C5 C6 . . 105.79(15) ?
C13 C5 C6 . . 123.02(17) ?
C14 C5 C6 . . 120.92(17) ?
C5 C6 C7 . . 118.11(15) ?
C5 C6 C2 . . 105.17(14) ?
C7 C6 C2 . . 102.28(14) ?
C5 C6 H6A . . 110.2 ?
C7 C6 H6A . . 110.2 ?
C2 C6 H6A . . 110.2 ?
C8 C7 C10 . . 99.26(15) ?
C8 C7 C6 . . 107.61(16) ?
C10 C7 C6 . . 99.27(14) ?
C8 C7 H7A . . 116.1 ?
C10 C7 H7A . . 116.1 ?
C6 C7 H7A . . 116.1 ?
C9 C8 C7 . . 108.46(17) ?
C9 C8 H8A . . 125.8 ?
C7 C8 H8A . . 125.8 ?
C8 C9 C1 . . 107.59(16) ?
C8 C9 H9A . . 126.2 ?
C1 C9 H9A . . 126.2 ?
C12 C10 C11 . . 61.07(14) ?
C12 C10 C1 . . 125.94(18) ?
C11 C10 C1 . . 126.01(17) ?
C12 C10 C7 . . 125.59(17) ?
C11 C10 C7 . . 125.14(17) ?
C1 C10 C7 . . 94.78(15) ?
C10 C11 C12 . . 59.39(13) ?
C10 C11 H11A . . 117.8 ?
C12 C11 H11A . . 117.8 ?
C10 C11 H11B . . 117.8 ?
C12 C11 H11B . . 117.8 ?
H11A C11 H11B . . 115 ?
C10 C12 C11 . . 59.55(14) ?
C10 C12 H12A . . 117.8 ?
C11 C12 H12A . . 117.8 ?
C10 C12 H12B . . 117.8 ?
C11 C12 H12B . . 117.8 ?
H12A C12 H12B . . 115 ?
C14 C13 C5 . . 60.73(13) ?
C14 C13 H13A . . 117.7 ?
C5 C13 H13A . . 117.7 ?
C14 C13 H13B . . 117.7 ?
C5 C13 H13B . . 117.7 ?
H13A C13 H13B . . 114.8 ?
C13 C14 C5 . . 60.28(13) ?
C13 C14 H14B . . 117.7 ?
C5 C14 H14B . . 117.7 ?
C13 C14 H14C . . 117.7 ?
C5 C14 H14C . . 117.7 ?
H14B C14 H14C . . 114.9 ?
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 C9 . 1.496(3) ?
C1 C10 . 1.513(3) ?
C1 C2 . 1.566(3) ?
C1 H1A . 0.98 ?
C2 C3 . 1.500(3) ?
C2 C6 . 1.564(2) ?
C2 H2A . 0.98 ?
C3 C4 . 1.312(3) ?
C3 H3A . 0.93 ?
C4 C5 . 1.470(3) ?
C4 H4A . 0.93 ?
C5 C13 . 1.503(3) ?
C5 C14 . 1.509(3) ?
C5 C6 . 1.532(3) ?
C6 C7 . 1.556(3) ?
C6 H6A . 0.98 ?
C7 C8 . 1.500(3) ?
C7 C10 . 1.525(2) ?
C7 H7A . 0.98 ?
C8 C9 . 1.309(3) ?
C8 H8A . 0.93 ?
C9 H9A . 0.93 ?
C10 C12 . 1.489(3) ?
C10 C11 . 1.491(3) ?
C11 C12 . 1.514(3) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 C14 . 1.483(3) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 H14B . 0.97 ?
C14 H14C . 0.97 ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C1 C2 C3 . . . . 45.1(2) ?
C10 C1 C2 C3 . . . . 148.69(16) ?
C9 C1 C2 C6 . . . . -67.80(18) ?
C10 C1 C2 C6 . . . . 35.83(17) ?
C6 C2 C3 C4 . . . . -0.8(2) ?
C1 C2 C3 C4 . . . . -113.1(2) ?
C2 C3 C4 C5 . . . . -1.3(3) ?
C3 C4 C5 C13 . . . . 150.9(2) ?
C3 C4 C5 C14 . . . . -138.8(2) ?
C3 C4 C5 C6 . . . . 2.8(2) ?
C4 C5 C6 C7 . . . . 110.17(18) ?
C13 C5 C6 C7 . . . . -37.6(3) ?
C14 C5 C6 C7 . . . . -108.5(2) ?
C4 C5 C6 C2 . . . . -3.09(19) ?
C13 C5 C6 C2 . . . . -150.86(18) ?
C14 C5 C6 C2 . . . . 138.22(18) ?
C3 C2 C6 C5 . . . . 2.37(18) ?
C1 C2 C6 C5 . . . . 125.38(16) ?
C3 C2 C6 C7 . . . . -121.60(17) ?
C1 C2 C6 C7 . . . . 1.41(17) ?
C5 C6 C7 C8 . . . . -49.8(2) ?
C2 C6 C7 C8 . . . . 65.04(17) ?
C5 C6 C7 C10 . . . . -152.68(15) ?
C2 C6 C7 C10 . . . . -37.84(17) ?
C10 C7 C8 C9 . . . . 32.5(2) ?
C6 C7 C8 C9 . . . . -70.4(2) ?
C7 C8 C9 C1 . . . . 0.2(2) ?
C10 C1 C9 C8 . . . . -33.2(2) ?
C2 C1 C9 C8 . . . . 70.0(2) ?
C9 C1 C10 C12 . . . . -91.6(2) ?
C2 C1 C10 C12 . . . . 159.29(19) ?
C9 C1 C10 C11 . . . . -169.39(19) ?
C2 C1 C10 C11 . . . . 81.5(2) ?
C9 C1 C10 C7 . . . . 49.82(17) ?
C2 C1 C10 C7 . . . . -59.27(16) ?
C8 C7 C10 C12 . . . . 92.4(2) ?
C6 C7 C10 C12 . . . . -157.93(19) ?
C8 C7 C10 C11 . . . . 169.4(2) ?
C6 C7 C10 C11 . . . . -80.9(2) ?
C8 C7 C10 C1 . . . . -49.28(17) ?
C6 C7 C10 C1 . . . . 60.43(16) ?
C1 C10 C11 C12 . . . . 115.3(2) ?
C7 C10 C11 C12 . . . . -115.1(2) ?
C1 C10 C12 C11 . . . . -115.4(2) ?
C7 C10 C12 C11 . . . . 114.4(2) ?
C4 C5 C13 C14 . . . . 108.4(2) ?
C6 C5 C13 C14 . . . . -108.9(2) ?
C4 C5 C14 C13 . . . . -111.8(2) ?
C6 C5 C14 C13 . . . . 112.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 490537
