#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/87/2218785.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_2218785
loop_
_publ_author_name
'Riddell, Nicole'
'McCrindle, Robert'
'Arsenault, Gilles'
'Lough, Alan J'
_publ_section_title
(1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18-Undecachloropentacyclo[12.2.1.1^6,9^.0^2,13^.0^5,10^]octadeca-7,15-diene
_journal_coeditor_code           PK2101
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1250
_journal_paper_doi               10.1107/S160053680801622X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H13 Cl11'
_chemical_formula_moiety         'C18 H13 Cl11'
_chemical_formula_sum            'C18 H13 Cl11'
_chemical_formula_weight         619.23
_chemical_name_systematic
;
(1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18-
Undecachloropentacyclo[12.2.1.1^6,9^.0^2,13^.0^5,10^]octadeca-7,15-diene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.505(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3129(5)
_cell_length_b                   12.1263(6)
_cell_length_c                   14.7229(7)
_cell_measurement_reflns_used    15654
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     2344.18(18)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15654
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.309
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.681
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0314P)²+4.5718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                3481
_reflns_number_total             5338
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2101.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218785
_cod_database_fobs_code          2218785
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1A 0.12630(8) 0.59357(8) 0.23239(6) 0.0351(3) Uani d . 1 . .
Cl Cl2A -0.04105(8) 0.77914(9) 0.28215(7) 0.0390(3) Uani d . 1 . .
Cl Cl3A 0.03958(8) 0.87394(8) 0.49922(7) 0.0371(3) Uani d . 1 . .
Cl Cl4A 0.25958(7) 0.75232(9) 0.58340(7) 0.0375(3) Uani d . 1 . .
Cl Cl5A 0.28655(8) 0.77926(10) 0.35627(7) 0.0449(3) Uani d . 1 . .
Cl Cl6A 0.32477(14) 0.57426(16) 0.42481(15) 0.0351(5) Uani d P 0.50 A 1
C C1A 0.0896(3) 0.5390(3) 0.4083(2) 0.0235(8) Uani d . 1 . .
H H1A 0.1293 0.4710 0.3993 0.028 Uiso calc R 1 . .
C C2A 0.1294(3) 0.5849(3) 0.5085(2) 0.0229(8) Uani d . 1 . .
H H2A 0.1854 0.5355 0.5384 0.027 Uiso calc R 1 . .
C C3A 0.0525(3) 0.5978(3) 0.5746(2) 0.0246(8) Uani d . 1 . .
H H3A1 -0.0099 0.6331 0.5412 0.030 Uiso calc R 1 . .
H H3A2 0.0817 0.6477 0.6254 0.030 Uiso calc R 1 . .
C C4A -0.0227(3) 0.5119(3) 0.3837(2) 0.0268(8) Uani d . 1 . .
H H4A1 -0.0412 0.5080 0.3158 0.032 Uiso calc R 1 . .
H H4A2 -0.0626 0.5724 0.4054 0.032 Uiso calc R 1 . .
C C5A 0.1236(3) 0.6328(3) 0.3464(2) 0.0255(8) Uani d . 1 . .
C C6A 0.0612(3) 0.7346(3) 0.3593(3) 0.0263(8) Uani d . 1 . .
C C7A 0.0923(3) 0.7720(3) 0.4438(3) 0.0243(8) Uani d . 1 . .
C C8A 0.1776(3) 0.6973(3) 0.4878(2) 0.0245(8) Uani d . 1 A .
C C9A 0.2268(3) 0.6680(3) 0.4039(3) 0.0289(9) Uani d . 1 A 1
H H9C 0.2739 0.6037 0.4170 0.035 Uiso calc PR 0.50 A 2
Cl Cl1B 0.50434(8) 0.70192(12) 0.26767(8) 0.0573(4) Uani d . 1 . .
Cl Cl2B 0.68792(8) 0.51251(11) 0.29107(7) 0.0488(3) Uani d . 1 . .
Cl Cl3B 0.83732(7) 0.55922(9) 0.12642(7) 0.0400(3) Uani d . 1 . .
Cl Cl4B 0.74566(9) 0.77648(10) 0.00260(9) 0.0501(3) Uani d . 1 . .
Cl Cl5B 0.70173(9) 0.85653(11) 0.21603(10) 0.0647(4) Uani d . 1 . .
Cl Cl6B 0.52623(17) 0.8699(2) 0.0840(2) 0.0609(8) Uani d P 0.50 B 1
C C1B 0.5100(3) 0.6208(3) 0.0915(3) 0.0312(9) Uani d . 1 . .
H H1B 0.4460 0.6647 0.0747 0.037 Uiso calc R 1 . .
C C2B 0.5781(3) 0.6426(3) 0.0152(3) 0.0306(9) Uani d . 1 . .
H H2B 0.5410 0.6952 -0.0308 0.037 Uiso calc R 1 . .
C C3B 0.6089(3) 0.5433(3) -0.0368(3) 0.0310(9) Uani d . 1 . .
H H3B1 0.6333 0.4843 0.0079 0.037 Uiso calc R 1 . .
H H3B2 0.6663 0.5644 -0.0683 0.037 Uiso calc R 1 . .
C C4B 0.4792(3) 0.5024(3) 0.1091(3) 0.0304(9) Uani d . 1 . .
H H4B1 0.4586 0.4988 0.1706 0.037 Uiso calc R 1 . .
H H4B2 0.5394 0.4542 0.1104 0.037 Uiso calc R 1 . .
C C5B 0.5738(3) 0.6757(4) 0.1780(3) 0.0362(10) Uani d . 1 . .
C C6B 0.6701(3) 0.6059(4) 0.2039(3) 0.0344(10) Uani d . 1 . .
C C7B 0.7274(3) 0.6241(3) 0.1398(3) 0.0324(9) Uani d . 1 . .
C C8B 0.6712(3) 0.7049(3) 0.0715(3) 0.0343(9) Uani d . 1 B .
C C9B 0.6180(3) 0.7760(4) 0.1363(3) 0.0444(11) Uani d . 1 B 1
H H9D 0.5630 0.8225 0.1008 0.053 Uiso calc PR 0.50 B 2
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
C4A C1A C5A . . 112.7(3)
C4A C1A C2A . . 117.6(3)
C5A C1A C2A . . 101.6(3)
C4A C1A H1A . . 108.1
C5A C1A H1A . . 108.1
C2A C1A H1A . . 108.1
C3A C2A C8A . . 112.0(3)
C3A C2A C1A . . 118.2(3)
C8A C2A C1A . . 102.2(3)
C3A C2A H2A . . 108.0
C8A C2A H2A . . 108.0
C1A C2A H2A . . 108.0
C2A C3A C4A . 3_566 114.1(3)
C2A C3A H3A1 . . 108.7
C4A C3A H3A1 3_566 . 108.7
C2A C3A H3A2 . . 108.7
C4A C3A H3A2 3_566 . 108.7
H3A1 C3A H3A2 . . 107.6
C1A C4A C3A . 3_566 113.6(3)
C1A C4A H4A1 . . 108.8
C3A C4A H4A1 3_566 . 108.8
C1A C4A H4A2 . . 108.8
C3A C4A H4A2 3_566 . 108.8
H4A1 C4A H4A2 . . 107.7
C6A C5A C9A . . 99.3(3)
C6A C5A C1A . . 107.5(3)
C9A C5A C1A . . 101.4(3)
C6A C5A Cl1A . . 116.0(3)
C9A C5A Cl1A . . 116.2(2)
C1A C5A Cl1A . . 114.4(3)
C7A C6A C5A . . 107.6(3)
C7A C6A Cl2A . . 127.4(3)
C5A C6A Cl2A . . 124.5(3)
C6A C7A C8A . . 107.1(3)
C6A C7A Cl3A . . 127.7(3)
C8A C7A Cl3A . . 124.8(3)
C7A C8A C9A . . 100.6(3)
C7A C8A C2A . . 107.6(3)
C9A C8A C2A . . 101.5(3)
C7A C8A Cl4A . . 116.0(3)
C9A C8A Cl4A . . 116.2(3)
C2A C8A Cl4A . . 113.3(3)
C8A C9A C5A . . 92.6(3)
C8A C9A Cl6A . . 114.9(3)
C5A C9A Cl6A . . 119.6(3)
C8A C9A Cl5A . . 115.0(3)
C5A C9A Cl5A . . 114.2(3)
Cl6A C9A Cl5A . . 101.4(2)
C4B C1B C5B . . 112.8(3)
C4B C1B C2B . . 118.7(3)
C5B C1B C2B . . 102.2(3)
C4B C1B H1B . . 107.5
C5B C1B H1B . . 107.5
C2B C1B H1B . . 107.5
C3B C2B C8B . . 113.2(3)
C3B C2B C1B . . 117.4(3)
C8B C2B C1B . . 101.6(3)
C3B C2B H2B . . 108.1
C8B C2B H2B . . 108.1
C1B C2B H2B . . 108.1
C2B C3B C4B . 3_665 113.1(3)
C2B C3B H3B1 . . 109.0
C4B C3B H3B1 3_665 . 109.0
C2B C3B H3B2 . . 109.0
C4B C3B H3B2 3_665 . 109.0
H3B1 C3B H3B2 . . 107.8
C1B C4B C3B . 3_665 114.4(3)
C1B C4B H4B1 . . 108.7
C3B C4B H4B1 3_665 . 108.7
C1B C4B H4B2 . . 108.7
C3B C4B H4B2 3_665 . 108.7
H4B1 C4B H4B2 . . 107.6
C9B C5B C6B . . 100.3(3)
C9B C5B C1B . . 101.9(3)
C6B C5B C1B . . 106.8(3)
C9B C5B Cl1B . . 116.3(3)
C6B C5B Cl1B . . 115.8(3)
C1B C5B Cl1B . . 114.0(3)
C7B C6B C5B . . 106.7(4)
C7B C6B Cl2B . . 128.5(3)
C5B C6B Cl2B . . 124.3(3)
C6B C7B C8B . . 107.5(3)
C6B C7B Cl3B . . 127.8(4)
C8B C7B Cl3B . . 124.4(3)
C7B C8B C9B . . 100.3(3)
C7B C8B C2B . . 107.5(3)
C9B C8B C2B . . 101.2(3)
C7B C8B Cl4B . . 116.0(3)
C9B C8B Cl4B . . 116.2(3)
C2B C8B Cl4B . . 113.8(3)
C5B C9B C8B . . 92.9(3)
C5B C9B Cl6B . . 114.1(3)
C8B C9B Cl6B . . 116.7(3)
C5B C9B Cl5B . . 114.6(3)
C8B C9B Cl5B . . 114.5(3)
Cl6B C9B Cl5B . . 104.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1A C5A . 1.751(4)
Cl2A C6A . 1.710(4)
Cl3A C7A . 1.696(4)
Cl4A C8A . 1.763(4)
Cl5A C9A . 1.769(4)
Cl6A C9A . 1.720(4)
C1A C4A . 1.515(5)
C1A C5A . 1.570(5)
C1A C2A . 1.584(5)
C1A H1A . 1.0000
C2A C3A . 1.533(5)
C2A C8A . 1.558(5)
C2A H2A . 1.0000
C3A C4A 3_566 1.544(5)
C3A H3A1 . 0.9900
C3A H3A2 . 0.9900
C4A C3A 3_566 1.544(5)
C4A H4A1 . 0.9900
C4A H4A2 . 0.9900
C5A C6A . 1.518(5)
C5A C9A . 1.548(5)
C6A C7A . 1.324(5)
C7A C8A . 1.512(5)
C8A C9A . 1.533(5)
Cl1B C5B . 1.761(4)
Cl2B C6B . 1.698(4)
Cl3B C7B . 1.701(4)
Cl4B C8B . 1.760(4)
Cl5B C9B . 1.772(4)
Cl6B C9B . 1.752(5)
C1B C4B . 1.527(6)
C1B C5B . 1.559(5)
C1B C2B . 1.579(5)
C1B H1B . 1.0000
C2B C3B . 1.518(5)
C2B C8B . 1.567(5)
C2B H2B . 1.0000
C3B C4B 3_665 1.551(5)
C3B H3B1 . 0.9900
C3B H3B2 . 0.9900
C4B C3B 3_665 1.551(5)
C4B H4B1 . 0.9900
C4B H4B2 . 0.9900
C5B C9B . 1.524(7)
C5B C6B . 1.531(6)
C6B C7B . 1.328(5)
C7B C8B . 1.511(6)
C8B C9B . 1.542(6)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1B H1B Cl4A 4_575 1.00 2.70 3.656(4) 160
