#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/81/2008106.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_2008106
loop_
_publ_author_name
'Boese, Roland'
'Roth, Wolfgang R.'
'Bläser, Dieter'
'Latz, Rüdiger'
'Bäumen, Anja'
_publ_section_title
;
 6,7-Dimethyltricyclo[3.2.2.0]non-6-ene at 120 K, a [3.2.2]propellane
 derivative
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9800075
_journal_paper_doi               10.1107/S0108270199099941
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          'C11 H16'
_chemical_formula_moiety         'C11 H16'
_chemical_formula_sum            'C11 H16'
_chemical_formula_weight         148.24
_chemical_name_systematic
;
 6,7-Dimethyltricyclo[3.2.2.0]non-6-ene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 112.821(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.329(3)
_cell_length_b                   6.6648(16)
_cell_length_c                   12.995(3)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      20
_cell_volume                     904.4(4)
_computing_cell_refinement       P3-VMS
_computing_data_collection       'P3-VMS (Siemens 1991)'
_computing_data_reduction        'XDISK (PC Version 4.20.2; Siemens, 1991)'
_computing_molecular_graphics    SHELXL97
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measurement_device_type  'Nicolet R3m/V four-circle'
_diffrn_measurement_method       Wyckoff
_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  0.028
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            6804
_diffrn_reflns_theta_max         45
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             328
_exptl_crystal_size_max          5.0
_exptl_crystal_size_rad          0.15
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.277
_refine_ls_extinction_coef       0.010(5)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         5171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0467
_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)+(0.0875P)² + 0.0436P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                4530
_reflns_number_total             5171
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0072.cif
_cod_data_source_block           qa0072
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2008106
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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
C1 1.04606(5) 0.07483(8) 0.28474(4) 0.01690(8) Uani d . 1 . . C
C2 0.97827(5) 0.07802(8) 0.15454(4) 0.01666(8) Uani d . 1 . . C
C3 0.87524(5) -0.04898(7) 0.17006(4) 0.01632(8) Uani d . 1 . . C
C4 0.93385(5) -0.05228(7) 0.28260(4) 0.01608(8) Uani d . 1 . . C
C5 1.09198(6) -0.04411(10) 0.14581(5) 0.02376(11) Uani d . 1 . . C
H5A 1.1397(12) 0.0349(17) 0.1081(10) 0.036(3) Uiso d . 1 . . H
H5B 1.0693(11) -0.1775(16) 0.1101(9) 0.033(3) Uiso d . 1 . . H
C6 1.15994(6) -0.04621(10) 0.27539(5) 0.02417(11) Uani d . 1 . . C
H6A 1.1766(13) -0.1838(18) 0.3116(11) 0.043(3) Uiso d . 1 . . H
H6B 1.2431(11) 0.0321(18) 0.3047(10) 0.034(3) Uiso d . 1 . . H
C7 1.06082(6) 0.29262(9) 0.32400(5) 0.02169(10) Uani d . 1 . . C
H7A 1.1463(11) 0.3394(16) 0.3359(9) 0.030(3) Uiso d . 1 . . H
H7B 1.0504(12) 0.3153(16) 0.3956(9) 0.033(3) Uiso d . 1 . . H
C8 0.95865(6) 0.40562(9) 0.22591(5) 0.02354(11) Uani d . 1 . . C
H8A 0.9745(11) 0.5530(17) 0.2258(10) 0.033(3) Uiso d . 1 . . H
H8B 0.8730(11) 0.3939(17) 0.2288(9) 0.030(3) Uiso d . 1 . . H
C9 0.95360(6) 0.29717(8) 0.11895(5) 0.02136(10) Uani d . 1 . . C
H9A 0.8690(12) 0.3244(16) 0.0538(9) 0.031(3) Uiso d . 1 . . H
H9B 1.0221(11) 0.3487(17) 0.0955(9) 0.029(2) Uiso d . 1 . . H
C10 0.76098(6) -0.15198(9) 0.08744(5) 0.02301(11) Uani d . 1 . . C
H10A 0.7014(12) -0.0601(18) 0.0378(11) 0.039(3) Uiso d . 1 . . H
H10B 0.7854(13) -0.243(2) 0.0409(10) 0.045(3) Uiso d . 1 . . H
H10C 0.7157(11) -0.2280(17) 0.1252(9) 0.031(3) Uiso d . 1 . . H
C11 0.91069(6) -0.16230(9) 0.37300(5) 0.02096(10) Uani d . 1 . . C
H11A 0.8972(11) -0.0721(18) 0.4284(10) 0.034(3) Uiso d . 1 . . H
H11B 0.9889(12) -0.240(2) 0.4201(10) 0.039(3) Uiso d . 1 . . H
H11C 0.8386(11) -0.2588(18) 0.3420(10) 0.034(3) Uiso d . 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 0.0033 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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 0 4
4 -3 -4
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 C1 C7 121.26(5)
C4 C1 C2 86.07(4)
C7 C1 C2 107.03(4)
C4 C1 C6 114.85(5)
C7 C1 C6 121.95(5)
C2 C1 C6 89.81(4)
C3 C2 C9 120.98(5)
C3 C2 C1 85.93(4)
C9 C2 C1 107.25(4)
C3 C2 C5 114.64(5)
C9 C2 C5 122.38(5)
C1 C2 C5 89.93(4)
C4 C3 C10 134.17(5)
C4 C3 C2 94.16(4)
C10 C3 C2 131.24(5)
C3 C4 C11 134.21(5)
C3 C4 C1 93.85(4)
C11 C4 C1 131.40(5)
C6 C5 C2 90.11(4)
C6 C5 H5A 113.4(7)
C2 C5 H5A 112.1(7)
C6 C5 H5B 115.4(6)
C2 C5 H5B 115.5(7)
H5A C5 H5B 109.4(9)
C5 C6 C1 90.15(4)
C5 C6 H6A 115.8(7)
C1 C6 H6A 116.1(8)
C5 C6 H6B 113.6(7)
C1 C6 H6B 112.3(7)
H6A C6 H6B 108.2(10)
C1 C7 C8 103.76(5)
C1 C7 H7A 109.4(6)
C8 C7 H7A 110.9(7)
C1 C7 H7B 114.8(6)
C8 C7 H7B 112.0(7)
H7A C7 H7B 106.0(9)
C7 C8 C9 105.56(5)
C7 C8 H8A 113.8(7)
C9 C8 H8A 113.7(7)
C7 C8 H8B 111.2(7)
C9 C8 H8B 107.6(7)
H8A C8 H8B 104.9(10)
C2 C9 C8 103.67(5)
C2 C9 H9A 115.2(6)
C8 C9 H9A 111.0(6)
C2 C9 H9B 110.5(6)
C8 C9 H9B 110.6(6)
H9A C9 H9B 106.1(9)
C3 C10 H10A 112.4(7)
C3 C10 H10B 111.1(8)
H10A C10 H10B 106.1(11)
C3 C10 H10C 110.8(6)
H10A C10 H10C 107.5(10)
H10B C10 H10C 108.8(10)
C4 C11 H11A 113.3(7)
C4 C11 H11B 110.5(7)
H11A C11 H11B 102.5(10)
C4 C11 H11C 111.5(7)
H11A C11 H11C 110.6(9)
H11B C11 H11C 107.9(10)
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 C4 . 1.5189(8) ?
C1 C7 . 1.5262(8) ?
C1 C2 . 1.5637(8) ?
C1 C6 . 1.5658(8) ?
C2 C3 . 1.5172(8) ?
C2 C9 . 1.5248(8) ?
C2 C5 . 1.5647(8) ?
C3 C4 . 1.3517(8) ?
C3 C10 . 1.4905(8) ?
C4 C11 . 1.4919(8) ?
C5 C6 . 1.5566(10) ?
C5 H5A . 1.008(12) ?
C5 H5B . 0.990(11) ?
C6 H6A . 1.015(12) ?
C6 H6B . 1.013(12) ?
C7 C8 . 1.5451(10) ?
C7 H7A . 0.971(11) ?
C7 H7B . 0.994(11) ?
C8 C9 . 1.5479(9) ?
C8 H8A . 0.999(12) ?
C8 H8B . 0.989(12) ?
C9 H9A . 1.019(12) ?
C9 H9B . 0.998(11) ?
C10 H10A . 0.953(12) ?
C10 H10B . 0.970(13) ?
C10 H10C . 0.978(11) ?
C11 H11A . 0.994(12) ?
C11 H11B . 1.002(13) ?
C11 H11C . 0.994(12) ?
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
C4 C1 C2 C3 0.11(3)
C7 C1 C2 C3 -121.42(4)
C6 C1 C2 C3 115.04(4)
C4 C1 C2 C9 121.33(5)
C7 C1 C2 C9 -0.21(6)
C6 C1 C2 C9 -123.75(5)
C4 C1 C2 C5 -114.60(4)
C7 C1 C2 C5 123.87(5)
C6 C1 C2 C5 0.33(4)
C9 C2 C3 C4 -107.83(5)
C1 C2 C3 C4 -0.13(4)
C5 C2 C3 C4 87.92(5)
C9 C2 C3 C10 79.05(7)
C1 C2 C3 C10 -173.25(6)
C5 C2 C3 C10 -85.20(7)
C10 C3 C4 C11 0.93(10)
C2 C3 C4 C11 -171.86(6)
C10 C3 C4 C1 172.92(6)
C2 C3 C4 C1 0.13(4)
C7 C1 C4 C3 107.44(5)
C2 C1 C4 C3 -0.13(4)
C6 C1 C4 C3 -88.10(5)
C7 C1 C4 C11 -80.21(7)
C2 C1 C4 C11 172.22(6)
C6 C1 C4 C11 84.25(7)
C3 C2 C5 C6 -85.81(5)
C9 C2 C5 C6 110.18(6)
C1 C2 C5 C6 -0.33(4)
C2 C5 C6 C1 0.33(4)
C4 C1 C6 C5 85.25(5)
C7 C1 C6 C5 -110.40(6)
C2 C1 C6 C5 -0.33(4)
C4 C1 C7 C8 -74.59(6)
C2 C1 C7 C8 21.27(6)
C6 C1 C7 C8 122.05(6)
C1 C7 C8 C9 -34.70(6)
C3 C2 C9 C8 74.83(6)
C1 C2 C9 C8 -20.89(6)
C5 C2 C9 C8 -122.15(6)
C7 C8 C9 C2 34.54(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21136627
