#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/86/2218611.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_2218611
loop_
_publ_author_name
'Riddell, Nicole'
'McCrindle, Robert'
'Arsenault, Gilles'
'Lough, Alan J'
_publ_section_title
(1R,2R,5R,6R,9S,10S,13S,14S)-1,6,7,8,9,14,15,16,17,17-Decachloropentacyclo[12.2.1.1^6,9^.0^2,13^.0^5,10^]octadeca-7,15-diene
_journal_coeditor_code           BT2716
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1249
_journal_paper_doi               10.1107/S1600536808016231
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H14 Cl10'
_chemical_formula_moiety         'C18 H14 Cl10'
_chemical_formula_sum            'C18 H14 Cl10'
_chemical_formula_weight         584.79
_chemical_name_systematic
;
(1R,2R,5R,6R,9S,10S,13S,14S)-
1,6,7,8,9,14,15,16,17,17-
Decachloropentacyclo[12.2.1.1^6,9^.0^2,13^.0^5,10^]octadeca-7,15-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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4341(2)
_cell_length_b                   12.9704(3)
_cell_length_c                   15.0389(4)
_cell_measurement_reflns_used    17031
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     2230.34(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17031
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.255
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.323
_refine_ls_abs_structure_details 'Flack (1983), 2207 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0319
_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)+(0.03P)²+1.1170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                4585
_reflns_number_total             5087
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2716.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2218611
_cod_database_fobs_code          2218611
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
Cl Cl1 0.87131(5) 0.78434(5) 0.55246(4) 0.02288(14) Uani d . 1
Cl Cl2 1.07256(5) 0.66212(5) 0.43725(5) 0.02523(14) Uani d . 1
Cl Cl3 1.14507(6) 0.81013(6) 0.25760(5) 0.03027(16) Uani d . 1
Cl Cl4 0.97237(6) 1.01756(5) 0.25571(5) 0.03129(16) Uani d . 1
Cl Cl5 1.03310(6) 0.98603(5) 0.47707(4) 0.02853(16) Uani d . 1
Cl Cl6 0.78892(6) 1.00833(5) 0.44082(5) 0.03032(16) Uani d . 1
Cl Cl7 0.68597(7) 0.61445(6) -0.03570(5) 0.03760(18) Uani d . 1
Cl Cl8 0.45590(8) 0.74067(6) 0.04705(6) 0.0468(2) Uani d . 1
Cl Cl9 0.36780(6) 0.61715(7) 0.23695(6) 0.0441(2) Uani d . 1
Cl Cl10 0.53873(7) 0.41158(6) 0.26610(5) 0.0406(2) Uani d . 1
C C1 0.7915(2) 0.78678(19) 0.37527(16) 0.0184(5) Uani d . 1
H H1A 0.7177 0.8161 0.4004 0.022 Uiso calc R 1
C C2 0.8244(2) 0.8505(2) 0.28950(17) 0.0195(5) Uani d . 1
H H2A 0.7614 0.9026 0.2790 0.023 Uiso calc R 1
C C3 0.8459(2) 0.7930(2) 0.20247(17) 0.0205(5) Uani d . 1
H H3A 0.8959 0.7325 0.2154 0.025 Uiso calc R 1
H H3B 0.8907 0.8389 0.1624 0.025 Uiso calc R 1
C C4 0.7364(2) 0.75489(19) 0.15180(17) 0.0197(5) Uani d . 1
H H4A 0.6656 0.7817 0.1818 0.024 Uiso calc R 1
H H4B 0.7378 0.7832 0.0907 0.024 Uiso calc R 1
C C5 0.7288(2) 0.63674(19) 0.14688(17) 0.0190(5) Uani d . 1
H H5A 0.8081 0.6103 0.1306 0.023 Uiso calc R 1
C C6 0.6879(2) 0.57719(19) 0.23264(17) 0.0192(5) Uani d . 1
H H6A 0.7506 0.5264 0.2479 0.023 Uiso calc R 1
C C7 0.6627(2) 0.6394(2) 0.31572(17) 0.0220(6) Uani d . 1
H H7A 0.6127 0.5982 0.3560 0.026 Uiso calc R 1
H H7B 0.6188 0.7023 0.2991 0.026 Uiso calc R 1
C C8 0.7757(2) 0.6710(2) 0.36566(17) 0.0205(5) Uani d . 1
H H8A 0.7746 0.6396 0.4257 0.025 Uiso calc R 1
H H8B 0.8440 0.6425 0.3335 0.025 Uiso calc R 1
C C9 0.8936(2) 0.81438(18) 0.43944(18) 0.0186(5) Uani d . 1
C C10 1.0060(2) 0.77145(19) 0.40053(17) 0.0194(5) Uani d . 1
C C11 1.0325(2) 0.8277(2) 0.32990(17) 0.0213(5) Uani d . 1
C C12 0.9372(2) 0.9089(2) 0.32037(17) 0.0212(5) Uani d . 1
C C13 0.9127(2) 0.93046(19) 0.42002(18) 0.0213(6) Uani d . 1
C C14 0.6406(2) 0.5965(2) 0.07546(17) 0.0239(6) Uani d . 1
C C15 0.5203(2) 0.6380(2) 0.09832(19) 0.0258(6) Uani d . 1
C C16 0.4856(2) 0.5901(2) 0.17161(19) 0.0257(6) Uani d . 1
C C17 0.5815(2) 0.5147(2) 0.19615(19) 0.0237(6) Uani d . 1
C C18 0.6255(3) 0.4837(2) 0.10393(18) 0.0252(6) Uani d . 1
H H18A 0.5664 0.4462 0.0683 0.030 Uiso calc R 1
H H18B 0.7000 0.4449 0.1056 0.030 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 0.0000 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
C8 C1 C9 112.1(2)
C8 C1 C2 117.9(2)
C9 C1 C2 102.00(19)
C8 C1 H1A 108.1
C9 C1 H1A 108.1
C2 C1 H1A 108.1
C3 C2 C12 110.9(2)
C3 C2 C1 118.9(2)
C12 C2 C1 101.96(19)
C3 C2 H2A 108.2
C12 C2 H2A 108.2
C1 C2 H2A 108.2
C2 C3 C4 116.6(2)
C2 C3 H3A 108.1
C4 C3 H3A 108.1
C2 C3 H3B 108.1
C4 C3 H3B 108.1
H3A C3 H3B 107.3
C5 C4 C3 112.9(2)
C5 C4 H4A 109.0
C3 C4 H4A 109.0
C5 C4 H4B 109.0
C3 C4 H4B 109.0
H4A C4 H4B 107.8
C4 C5 C14 113.8(2)
C4 C5 C6 117.8(2)
C14 C5 C6 101.98(19)
C4 C5 H5A 107.6
C14 C5 H5A 107.6
C6 C5 H5A 107.6
C7 C6 C17 114.7(2)
C7 C6 C5 118.1(2)
C17 C6 C5 101.4(2)
C7 C6 H6A 107.3
C17 C6 H6A 107.3
C5 C6 H6A 107.3
C6 C7 C8 112.5(2)
C6 C7 H7A 109.1
C8 C7 H7A 109.1
C6 C7 H7B 109.1
C8 C7 H7B 109.1
H7A C7 H7B 107.8
C1 C8 C7 114.0(2)
C1 C8 H8A 108.8
C7 C8 H8A 108.8
C1 C8 H8B 108.8
C7 C8 H8B 108.8
H8A C8 H8B 107.6
C10 C9 C13 99.5(2)
C10 C9 C1 108.2(2)
C13 C9 C1 102.2(2)
C10 C9 Cl1 114.42(17)
C13 C9 Cl1 114.65(18)
C1 C9 Cl1 116.00(18)
C11 C10 C9 107.5(2)
C11 C10 Cl2 128.1(2)
C9 C10 Cl2 124.01(19)
C10 C11 C12 107.0(2)
C10 C11 Cl3 127.8(2)
C12 C11 Cl3 125.06(19)
C11 C12 C13 99.4(2)
C11 C12 C2 106.4(2)
C13 C12 C2 103.0(2)
C11 C12 Cl4 116.30(19)
C13 C12 Cl4 115.59(18)
C2 C12 Cl4 114.32(18)
C9 C13 C12 91.88(19)
C9 C13 Cl6 114.20(18)
C12 C13 Cl6 114.79(18)
C9 C13 Cl5 114.36(18)
C12 C13 Cl5 113.56(18)
Cl6 C13 Cl5 107.68(13)
C15 C14 C18 100.0(2)
C15 C14 C5 108.1(2)
C18 C14 C5 101.5(2)
C15 C14 Cl7 115.73(19)
C18 C14 Cl7 115.04(18)
C5 C14 Cl7 114.65(19)
C16 C15 C14 107.1(2)
C16 C15 Cl8 127.8(2)
C14 C15 Cl8 124.5(2)
C15 C16 C17 106.8(2)
C15 C16 Cl9 128.3(2)
C17 C16 Cl9 124.4(2)
C16 C17 C18 100.8(2)
C16 C17 C6 108.4(2)
C18 C17 C6 101.5(2)
C16 C17 Cl10 115.6(2)
C18 C17 Cl10 115.51(19)
C6 C17 Cl10 113.47(19)
C17 C18 C14 92.2(2)
C17 C18 H18A 113.2
C14 C18 H18A 113.2
C17 C18 H18B 113.2
C14 C18 H18B 113.2
H18A C18 H18B 110.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C9 1.762(3)
Cl2 C10 1.701(3)
Cl3 C11 1.700(3)
Cl4 C12 1.758(3)
Cl5 C13 1.775(3)
Cl6 C13 1.766(3)
Cl7 C14 1.766(3)
Cl8 C15 1.706(3)
Cl9 C16 1.704(3)
Cl10 C17 1.771(3)
C1 C8 1.519(3)
C1 C9 1.557(3)
C1 C2 1.577(3)
C1 H1A 1.0000
C2 C3 1.526(4)
C2 C12 1.567(4)
C2 H2A 1.0000
C3 C4 1.547(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.537(3)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C14 1.563(4)
C5 C6 1.574(3)
C5 H5A 1.0000
C6 C7 1.515(4)
C6 C17 1.562(3)
C6 H6A 1.0000
C7 C8 1.550(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.518(3)
C9 C13 1.549(3)
C10 C11 1.324(4)
C11 C12 1.522(4)
C12 C13 1.550(4)
C14 C15 1.517(4)
C14 C18 1.534(4)
C15 C16 1.326(4)
C16 C17 1.514(4)
C17 C18 1.529(4)
C18 H18A 0.9900
C18 H18B 0.9900
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740175
