#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227403.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227403
loop_
_publ_author_name
'Benharref, Ahmed'
'El Ammari, Lahcen'
'Berraho, Moha'
'Lassaba, Esaadia'
_publ_section_title
;
 (1S,2S,4R)-3,3-Dichloro-4,8,12,12-tetramethyltricyclo[5.5.0.0^2,4^]dodeca-6,8-diene
;
_journal_coeditor_code           ER2079
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2463
_journal_paper_doi               10.1107/S1600536810034070
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H22 Cl2'
_chemical_formula_moiety         'C16 H22 Cl2'
_chemical_formula_sum            'C16 H22 Cl2'
_chemical_formula_weight         285.24
_chemical_name_systematic
;
(1S,2S,4R)-3,3-Dichloro-4,8,12,12-
tetramethyltricyclo[5.5.0.0^2,4^]dodeca-6,8-diene
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4356(17)
_cell_length_b                   8.3124(18)
_cell_length_c                   24.108(6)
_cell_measurement_reflns_used    10992
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      1.7
_cell_volume                     1490.1(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8 APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10992
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.417
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.294
_refine_ls_abs_structure_details 'Flack (1985), 1535 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0315
_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)+(0.0579P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0955
_reflns_number_gt                3282
_reflns_number_total             3691
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er2079.cif
_cod_data_source_block           I
_cod_database_code               2227403
_cod_database_fobs_code          2227403
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.6213(2) 0.33418(19) 0.89982(6) 0.0375(3) Uani d . 1 . .
C C2 0.4484(2) 0.3173(2) 0.92944(6) 0.0476(4) Uani d . 1 . .
C C3 0.3427(3) 0.4400(3) 0.94246(7) 0.0551(5) Uani d . 1 . .
C C4 0.3834(3) 0.6154(3) 0.93795(8) 0.0588(5) Uani d . 1 . .
H H4A 0.3146 0.6730 0.9658 0.071 Uiso calc R 1 . .
H H4B 0.3451 0.6535 0.9018 0.071 Uiso calc R 1 . .
C C5 0.5809(2) 0.6534(2) 0.94551(7) 0.0514(4) Uani d . 1 . .
H H5A 0.6290 0.5834 0.9741 0.062 Uiso calc R 1 . .
H H5B 0.5919 0.7633 0.9587 0.062 Uiso calc R 1 . .
C C6 0.6957(2) 0.63474(18) 0.89326(6) 0.0405(3) Uani d . 1 . .
C C7 0.6413(2) 0.47755(17) 0.86197(6) 0.0341(3) Uani d . 1 . .
H H7 0.5234 0.4970 0.8451 0.041 Uiso calc R 1 . .
C C8 0.7727(2) 0.44941(18) 0.81513(6) 0.0384(3) Uani d . 1 . .
H H8 0.8138 0.5487 0.7973 0.046 Uiso calc R 1 . .
C C9 0.7663(2) 0.30866(19) 0.77693(7) 0.0427(3) Uani d . 1 . .
C C10 0.9167(2) 0.3203(2) 0.81854(7) 0.0438(3) Uani d . 1 . .
C C11 0.9108(2) 0.2114(2) 0.86840(8) 0.0497(4) Uani d . 1 . .
H H11A 0.9257 0.1014 0.8558 0.060 Uiso calc R 1 . .
H H11B 1.0127 0.2368 0.8920 0.060 Uiso calc R 1 . .
C C12 0.7456(3) 0.2200(2) 0.90240(7) 0.0457(4) Uani d . 1 . .
C C13 1.1028(3) 0.3568(3) 0.79848(9) 0.0628(5) Uani d . 1 . .
H H13A 1.1600 0.2590 0.7867 0.094 Uiso calc R 1 . .
H H13B 1.1712 0.4044 0.8280 0.094 Uiso calc R 1 . .
H H13C 1.0966 0.4304 0.7679 0.094 Uiso calc R 1 . .
C C14 0.8912(3) 0.6291(2) 0.91128(8) 0.0546(4) Uani d . 1 . .
H H14A 0.9119 0.5336 0.9328 0.082 Uiso calc R 1 . .
H H14B 0.9181 0.7221 0.9334 0.082 Uiso calc R 1 . .
H H14C 0.9673 0.6280 0.8791 0.082 Uiso calc R 1 . .
C C15 0.6651(3) 0.7795(2) 0.85566(8) 0.0573(5) Uani d . 1 . .
H H15A 0.7378 0.7690 0.8229 0.086 Uiso calc R 1 . .
H H15B 0.6978 0.8761 0.8750 0.086 Uiso calc R 1 . .
H H15C 0.5406 0.7847 0.8453 0.086 Uiso calc R 1 . .
C C16 0.3883(3) 0.1489(3) 0.94230(11) 0.0727(6) Uani d . 1 . .
H H16A 0.4725 0.0996 0.9673 0.109 Uiso calc R 1 . .
H H16B 0.3825 0.0876 0.9086 0.109 Uiso calc R 1 . .
H H16C 0.2716 0.1518 0.9593 0.109 Uiso calc R 1 . .
Cl Cl1 0.59995(6) 0.16140(5) 0.781164(18) 0.05350(13) Uani d . 1 . .
Cl Cl2 0.81596(8) 0.34714(7) 0.706600(17) 0.06577(16) Uani d . 1 . .
H H3 0.223(3) 0.414(3) 0.9587(9) 0.074(6) Uiso d . 1 . .
H H12 0.732(3) 0.127(3) 0.9270(9) 0.064(6) Uiso d . 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'
Cl Cl 0.1484 0.1585 '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
C12 C1 C2 . . 121.04(16) ?
C12 C1 C7 . . 121.66(14) ?
C2 C1 C7 . . 116.97(14) ?
C3 C2 C1 . . 123.86(17) ?
C3 C2 C16 . . 119.48(18) ?
C1 C2 C16 . . 116.59(17) ?
C2 C3 C4 . . 127.88(17) ?
C2 C3 H3 . . 117.2(14) ?
C4 C3 H3 . . 114.8(13) ?
C3 C4 C5 . . 113.09(17) ?
C3 C4 H4A . . 109.0 ?
C5 C4 H4A . . 109.0 ?
C3 C4 H4B . . 109.0 ?
C5 C4 H4B . . 109.0 ?
H4A C4 H4B . . 107.8 ?
C4 C5 C6 . . 114.91(14) ?
C4 C5 H5A . . 108.5 ?
C6 C5 H5A . . 108.5 ?
C4 C5 H5B . . 108.5 ?
C6 C5 H5B . . 108.5 ?
H5A C5 H5B . . 107.5 ?
C14 C6 C15 . . 109.72(16) ?
C14 C6 C5 . . 107.57(14) ?
C15 C6 C5 . . 109.07(14) ?
C14 C6 C7 . . 111.10(13) ?
C15 C6 C7 . . 109.56(13) ?
C5 C6 C7 . . 109.78(13) ?
C1 C7 C8 . . 113.17(12) ?
C1 C7 C6 . . 113.22(12) ?
C8 C7 C6 . . 108.85(12) ?
C1 C7 H7 . . 107.1 ?
C8 C7 H7 . . 107.1 ?
C6 C7 H7 . . 107.1 ?
C9 C8 C7 . . 124.25(13) ?
C9 C8 C10 . . 60.05(10) ?
C7 C8 C10 . . 121.66(13) ?
C9 C8 H8 . . 113.6 ?
C7 C8 H8 . . 113.6 ?
C10 C8 H8 . . 113.6 ?
C8 C9 C10 . . 60.92(11) ?
C8 C9 Cl1 . . 122.54(11) ?
C10 C9 Cl1 . . 122.22(12) ?
C8 C9 Cl2 . . 116.42(12) ?
C10 C9 Cl2 . . 118.25(11) ?
Cl1 C9 Cl2 . . 109.39(9) ?
C13 C10 C11 . . 114.00(16) ?
C13 C10 C9 . . 118.97(15) ?
C11 C10 C9 . . 118.17(15) ?
C13 C10 C8 . . 119.41(16) ?
C11 C10 C8 . . 116.60(13) ?
C9 C10 C8 . . 59.03(10) ?
C12 C11 C10 . . 115.96(15) ?
C12 C11 H11A . . 108.3 ?
C10 C11 H11A . . 108.3 ?
C12 C11 H11B . . 108.3 ?
C10 C11 H11B . . 108.3 ?
H11A C11 H11B . . 107.4 ?
C1 C12 C11 . . 126.00(17) ?
C1 C12 H12 . . 121.5(13) ?
C11 C12 H12 . . 112.4(13) ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C6 C14 H14A . . 109.5 ?
C6 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C6 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C6 C15 H15A . . 109.5 ?
C6 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C6 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C2 C16 H16A . . 109.5 ?
C2 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C2 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
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 C12 . 1.326(2) ?
C1 C2 . 1.477(2) ?
C1 C7 . 1.508(2) ?
C2 C3 . 1.326(3) ?
C2 C16 . 1.502(3) ?
C3 C4 . 1.493(3) ?
C3 H3 . 1.00(3) ?
C4 C5 . 1.513(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.530(2) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C14 . 1.519(2) ?
C6 C15 . 1.524(2) ?
C6 C7 . 1.562(2) ?
C7 C8 . 1.511(2) ?
C7 H7 . 0.9800 ?
C8 C9 . 1.490(2) ?
C8 C10 . 1.518(2) ?
C8 H8 . 0.9800 ?
C9 C10 . 1.505(2) ?
C9 Cl1 . 1.7433(16) ?
C9 Cl2 . 1.7645(17) ?
C10 C13 . 1.497(2) ?
C10 C11 . 1.505(3) ?
C11 C12 . 1.479(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12 . 0.98(2) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745873
