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#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/25/8102545.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_8102545
loop_
_publ_author_name
'Brahim Boualy'
'Larbi El Firdoussi'
'Mustapha Ait Ali'
'Abdallah Karim'
'Anke Spannenberg'
_publ_section_title
;
 Crystal structure of
 (2S,4S,7S)-7,7-dichloro-4-(1-chloro-1-methyl-ethyl)-1-(2,2,2-trichloroethyl)-bicyclo[4.1.0]heptane,
 C12H16Cl6
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              631
_journal_volume                  224
_journal_year                    2009
_chemical_formula_sum            'C12 H16 Cl6'
_chemical_formula_weight         372.95
_chemical_name_systematic
; 
(2S,4S,7S)-7,7-Dichloro-4-(1-chloro-1-methyl-ethyl)
-1-(2,2,2-trichloro-ethyl)bicyclo[4.1.0]heptane 
;
_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                   6.0742(3)
_cell_length_b                   9.7189(6)
_cell_length_c                   26.7002(11)
_cell_measurement_reflns_used    7990
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      1.53
_cell_volume                     1576.23(14)
_computing_data_collection       STOE-X-AREA
_computing_molecular_graphics    XP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'STOE IPDS II'
_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  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0187
_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       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            24353
_diffrn_reflns_theta_full        26.68
_diffrn_reflns_theta_max         26.68
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_T_max  0.8824
_exptl_absorpt_correction_T_min  0.6727
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0185
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0307P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0442
_refine_ls_wR_factor_ref         0.0445
_reflns_number_gt                3116
_reflns_number_total             3339
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2758.cff
_cod_data_source_block           ks783
_cod_original_cell_volume        1576.22(13)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               8102545
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2968(2) 0.40966(14) 0.61857(6) 0.0258(3) Uani 1 1 d . . .
C2 C 0.1959(2) 0.28070(14) 0.59801(5) 0.0242(3) Uani 1 1 d . . .
H2 H 0.0343 0.2881 0.5914 0.029 Uiso 1 1 calc R . .
C3 C 0.3157(2) 0.18287(16) 0.56302(5) 0.0271(3) Uani 1 1 d . . .
H3A H 0.4297 0.2344 0.5443 0.033 Uiso 1 1 calc R . .
H3B H 0.2098 0.1450 0.5384 0.033 Uiso 1 1 calc R . .
C4 C 0.4248(2) 0.06415(14) 0.59135(5) 0.0234(3) Uani 1 1 d . . .
H4 H 0.3053 0.0166 0.6104 0.028 Uiso 1 1 calc R . .
C5 C 0.5807(2) 0.12587(15) 0.63020(5) 0.0246(3) Uani 1 1 d . . .
H5A H 0.6839 0.1899 0.6135 0.029 Uiso 1 1 calc R . .
H5B H 0.6683 0.0515 0.6458 0.029 Uiso 1 1 calc R . .
C6 C 0.4528(2) 0.20323(14) 0.67087(5) 0.0231(3) Uani 1 1 d . . .
H6A H 0.3985 0.1349 0.6954 0.028 Uiso 1 1 calc R . .
H6B H 0.5573 0.2642 0.6887 0.028 Uiso 1 1 calc R . .
C7 C 0.2579(2) 0.29006(13) 0.65400(5) 0.0211(3) Uani 1 1 d . . .
C8 C 0.0681(2) 0.29777(14) 0.69066(5) 0.0227(3) Uani 1 1 d . . .
H8A H 0.0039 0.2045 0.6937 0.027 Uiso 1 1 calc R . .
H8B H -0.0465 0.3579 0.6759 0.027 Uiso 1 1 calc R . .
C9 C 0.1181(3) 0.35047(15) 0.74357(6) 0.0270(3) Uani 1 1 d . . .
C10 C 0.5319(3) -0.04536(17) 0.55743(5) 0.0284(3) Uani 1 1 d . . .
C11 C 0.3732(4) -0.1025(2) 0.51888(7) 0.0501(5) Uani 1 1 d . . .
H11A H 0.3094 -0.0266 0.4996 0.075 Uiso 1 1 calc R . .
H11B H 0.2555 -0.1532 0.5359 0.075 Uiso 1 1 calc R . .
H11C H 0.4522 -0.1647 0.4963 0.075 Uiso 1 1 calc R . .
C12 C 0.6343(4) -0.16239(17) 0.58753(7) 0.0453(4) Uani 1 1 d . . .
H12A H 0.7373 -0.1244 0.6122 0.068 Uiso 1 1 calc R . .
H12B H 0.7133 -0.2244 0.5649 0.068 Uiso 1 1 calc R . .
H12C H 0.5180 -0.2135 0.6049 0.068 Uiso 1 1 calc R . .
Cl1 Cl 0.12619(7) 0.55663(4) 0.620604(15) 0.03446(9) Uani 1 1 d . . .
Cl2 Cl 0.56827(6) 0.45794(4) 0.604454(16) 0.03431(9) Uani 1 1 d . . .
Cl3 Cl 0.75787(8) 0.03420(5) 0.522458(16) 0.04404(11) Uani 1 1 d . . .
Cl4 Cl 0.25696(7) 0.22922(4) 0.782427(13) 0.03611(9) Uani 1 1 d . . .
Cl5 Cl -0.13878(7) 0.38643(4) 0.773991(15) 0.03830(10) Uani 1 1 d . . .
Cl6 Cl 0.27725(7) 0.50318(4) 0.741908(14) 0.03655(9) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 61.58(9) . . ?
C2 C1 Cl2 121.93(11) . . ?
C7 C1 Cl2 119.02(10) . . ?
C2 C1 Cl1 116.58(10) . . ?
C7 C1 Cl1 120.61(10) . . ?
Cl2 C1 Cl1 109.99(8) . . ?
C1 C2 C3 123.54(12) . . ?
C1 C2 C7 59.78(9) . . ?
C3 C2 C7 121.03(12) . . ?
C2 C3 C4 112.05(12) . . ?
C5 C4 C3 107.94(11) . . ?
C5 C4 C10 114.09(12) . . ?
C3 C4 C10 114.39(11) . . ?
C4 C5 C6 111.06(12) . . ?
C7 C6 C5 117.18(11) . . ?
C8 C7 C1 118.93(11) . . ?
C8 C7 C6 115.36(11) . . ?
C1 C7 C6 119.22(12) . . ?
C8 C7 C2 116.29(12) . . ?
C1 C7 C2 58.64(9) . . ?
C6 C7 C2 116.33(11) . . ?
C7 C8 C9 117.47(12) . . ?
C8 C9 Cl6 111.40(10) . . ?
C8 C9 Cl4 114.16(10) . . ?
Cl6 C9 Cl4 108.07(8) . . ?
C8 C9 Cl5 108.07(10) . . ?
Cl6 C9 Cl5 108.83(8) . . ?
Cl4 C9 Cl5 106.08(8) . . ?
C11 C10 C12 110.10(16) . . ?
C11 C10 C4 112.54(14) . . ?
C12 C10 C4 112.18(12) . . ?
C11 C10 Cl3 106.57(12) . . ?
C12 C10 Cl3 106.15(12) . . ?
C4 C10 Cl3 108.93(10) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.499(2) . ?
C1 C7 1.5171(18) . ?
C1 Cl2 1.7551(15) . ?
C1 Cl1 1.7657(14) . ?
C2 C3 1.519(2) . ?
C2 C7 1.5442(18) . ?
C3 C4 1.530(2) . ?
C4 C5 1.5275(19) . ?
C4 C10 1.542(2) . ?
C5 C6 1.5325(19) . ?
C6 C7 1.5219(19) . ?
C7 C8 1.5143(19) . ?
C8 C9 1.533(2) . ?
C9 Cl6 1.7719(15) . ?
C9 Cl4 1.7823(16) . ?
C9 Cl5 1.7934(16) . ?
C10 C11 1.516(2) . ?
C10 C12 1.525(2) . ?
C10 Cl3 1.8312(15) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653972
