#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/05/2230580.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_2230580
loop_
_publ_author_name
'Manohar, R.'
'Harikrishna, M.'
'Ramanathan, C. R.'
'SureshKumar, M.'
'Gunasekaran, K.'
_publ_section_title
;
 1,7,8,9,10,10-Hexachloro-4-(2-phenylethyl)-4-azatricyclo[5.2.1.0^2,6^]dec-8-ene-3,5-dione
;
_journal_coeditor_code           BT5543
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1708
_journal_paper_doi               10.1107/S1600536811022495
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H11 Cl6 N O2'
_chemical_formula_moiety         'C17 H11 Cl6 N O2'
_chemical_formula_sum            'C17 H11 Cl6 N O2'
_chemical_formula_weight         473.97
_chemical_name_systematic
;
1,7,8,9,10,10-Hexachloro-4-(2-phenylethyl)-4-azatricyclo[5.2.1.0^2,6^]dec-
8-ene-3,5-dione
;
_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                 111.276(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3009(5)
_cell_length_b                   13.6141(5)
_cell_length_c                   11.4912(4)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3
_cell_measurement_theta_min      3.0
_cell_volume                     1939.00(13)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       ω
_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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9237
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.30
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.898
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.542
_refine_ls_extinction_coef       0.0027(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.723
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.723
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0420
_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)+(0.0784P)²+2.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                2814
_reflns_number_total             4457
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5543.cif
_cod_data_source_block           I
_cod_original_cell_volume        1939.00(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230580
_cod_database_fobs_code          2230580
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2561(2) 0.08000(19) 0.4510(2) 0.0363(5) Uani d . 1 1 . .
C C2 0.31543(19) 0.02382(19) 0.3771(2) 0.0333(5) Uani d . 1 1 . .
C C3 0.36261(19) -0.0735(2) 0.4348(2) 0.0379(6) Uani d . 1 1 . .
C C5 0.2247(2) -0.1141(2) 0.2485(2) 0.0415(6) Uani d . 1 1 . .
C C6 0.22344(19) -0.0031(2) 0.2548(2) 0.0359(6) Uani d . 1 1 . .
C C7 0.1224(2) 0.0410(2) 0.2729(2) 0.0418(6) Uani d . 1 1 . .
C C8 0.1055(2) -0.0167(2) 0.3772(3) 0.0460(7) Uani d . 1 1 . .
C C9 0.1842(2) 0.0067(2) 0.4824(2) 0.0428(6) Uani d . 1 1 . .
C C10 0.1697(2) 0.1367(2) 0.3446(2) 0.0399(6) Uani d . 1 1 . .
C C11 0.3368(3) -0.2506(2) 0.3813(3) 0.0522(7) Uani d . 1 1 . .
H H11A 0.4144 -0.2567 0.4224 0.063 Uiso calc R 1 1 . .
H H11B 0.3154 -0.2875 0.3039 0.063 Uiso calc R 1 1 . .
C C12 0.2821(3) -0.2937(2) 0.4645(4) 0.0644(9) Uani d . 1 1 . .
H H12A 0.2923 -0.2501 0.5346 0.077 Uiso calc R 1 1 . .
H H12B 0.2052 -0.2993 0.4178 0.077 Uiso calc R 1 1 . .
C C13 0.3272(2) -0.3936(2) 0.5125(3) 0.0426(6) Uani d . 1 1 . .
C C14 0.4205(3) -0.4027(2) 0.6155(3) 0.0570(8) Uani d . 1 1 . .
H H14 0.4556 -0.3463 0.6557 0.068 Uiso calc R 1 1 . .
C C15 0.4629(3) -0.4925(3) 0.6604(3) 0.0676(9) Uani d . 1 1 . .
H H15 0.5260 -0.4965 0.7305 0.081 Uiso calc R 1 1 . .
C C16 0.4133(3) -0.5759(3) 0.6031(3) 0.0661(9) Uani d . 1 1 . .
H H16 0.4424 -0.6369 0.6338 0.079 Uiso calc R 1 1 . .
C C17 0.3213(3) -0.5699(2) 0.5008(3) 0.0634(9) Uani d . 1 1 . .
H H17 0.2874 -0.6270 0.4613 0.076 Uiso calc R 1 1 . .
C C18 0.2779(2) -0.4794(2) 0.4550(3) 0.0526(7) Uani d . 1 1 . .
H H18 0.2149 -0.4760 0.3848 0.063 Uiso calc R 1 1 . .
N N4 0.30886(18) -0.14704(16) 0.3532(2) 0.0403(5) Uani d . 1 1 . .
O O1 0.16542(18) -0.16633(17) 0.16898(19) 0.0610(6) Uani d . 1 1 . .
O O2 0.43337(15) -0.08669(16) 0.53428(18) 0.0539(5) Uani d . 1 1 . .
Cl Cl1 0.22370(7) 0.21660(6) 0.26068(7) 0.0601(2) Uani d . 1 1 . .
Cl Cl2 0.07822(7) 0.20423(6) 0.39214(7) 0.0620(2) Uani d . 1 1 . .
Cl Cl3 0.33930(7) 0.15230(6) 0.57446(7) 0.0663(3) Uani d . 1 1 . .
Cl Cl4 0.21264(9) -0.04238(8) 0.62570(8) 0.0806(3) Uani d . 1 1 . .
Cl Cl5 0.01097(7) 0.05813(9) 0.13594(8) 0.0834(3) Uani d . 1 1 . .
Cl Cl6 0.00951(8) -0.10391(8) 0.35359(11) 0.0894(4) Uani d . 1 1 . .
H H1 0.368(2) 0.062(2) 0.366(2) 0.043(7) Uiso d . 1 1 . .
H H2 0.232(2) 0.0211(19) 0.183(2) 0.039(7) Uiso d . 1 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C9 C1 C10 . . 99.5(2) ?
C9 C1 C2 . . 107.2(2) ?
C10 C1 C2 . . 101.12(18) ?
C9 C1 Cl3 . . 116.46(17) ?
C10 C1 Cl3 . . 115.44(18) ?
C2 C1 Cl3 . . 115.00(18) ?
C3 C2 C6 . . 105.0(2) ?
C3 C2 C1 . . 113.8(2) ?
C6 C2 C1 . . 102.91(19) ?
C3 C2 H1 . . 110.1(17) ?
C6 C2 H1 . . 113.8(17) ?
C1 C2 H1 . . 111.1(17) ?
O2 C3 N4 . . 124.8(3) ?
O2 C3 C2 . . 127.3(3) ?
N4 C3 C2 . . 107.9(2) ?
O1 C5 N4 . . 124.7(3) ?
O1 C5 C6 . . 127.8(3) ?
N4 C5 C6 . . 107.5(2) ?
C5 C6 C2 . . 105.2(2) ?
C5 C6 C7 . . 114.7(2) ?
C2 C6 C7 . . 103.08(18) ?
C5 C6 H2 . . 107.6(16) ?
C2 C6 H2 . . 114.6(16) ?
C7 C6 H2 . . 111.6(16) ?
C8 C7 C6 . . 106.8(2) ?
C8 C7 C10 . . 99.4(2) ?
C6 C7 C10 . . 101.1(2) ?
C8 C7 Cl5 . . 117.48(19) ?
C6 C7 Cl5 . . 115.15(17) ?
C10 C7 Cl5 . . 114.6(2) ?
C9 C8 C7 . . 107.7(2) ?
C9 C8 Cl6 . . 128.2(2) ?
C7 C8 Cl6 . . 123.8(2) ?
C8 C9 C1 . . 107.5(2) ?
C8 C9 Cl4 . . 128.4(2) ?
C1 C9 Cl4 . . 123.8(2) ?
C1 C10 C7 . . 92.4(2) ?
C1 C10 Cl2 . . 114.45(16) ?
C7 C10 Cl2 . . 114.29(18) ?
C1 C10 Cl1 . . 113.92(18) ?
C7 C10 Cl1 . . 113.21(17) ?
Cl2 C10 Cl1 . . 108.11(15) ?
N4 C11 C12 . . 111.8(2) ?
N4 C11 H11A . . 109.3 ?
C12 C11 H11A . . 109.3 ?
N4 C11 H11B . . 109.3 ?
C12 C11 H11B . . 109.3 ?
H11A C11 H11B . . 107.9 ?
C13 C12 C11 . . 111.3(2) ?
C13 C12 H12A . . 109.4 ?
C11 C12 H12A . . 109.4 ?
C13 C12 H12B . . 109.4 ?
C11 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C14 C13 C18 . . 117.3(3) ?
C14 C13 C12 . . 120.8(3) ?
C18 C13 C12 . . 122.0(3) ?
C15 C14 C13 . . 121.7(3) ?
C15 C14 H14 . . 119.1 ?
C13 C14 H14 . . 119.1 ?
C16 C15 C14 . . 120.2(3) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C17 . . 119.8(3) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
C16 C17 C18 . . 120.3(3) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C13 C18 C17 . . 120.7(3) ?
C13 C18 H18 . . 119.6 ?
C17 C18 H18 . . 119.6 ?
C3 N4 C5 . . 114.2(2) ?
C3 N4 C11 . . 121.4(2) ?
C5 N4 C11 . . 124.3(2) ?
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 C9 . 1.514(4) ?
C1 C10 . 1.547(3) ?
C1 C2 . 1.554(3) ?
C1 Cl3 . 1.751(2) ?
C2 C3 . 1.512(4) ?
C2 C6 . 1.535(3) ?
C2 H1 . 0.91(3) ?
C3 O2 . 1.202(3) ?
C3 N4 . 1.381(3) ?
C5 O1 . 1.200(3) ?
C5 N4 . 1.387(3) ?
C5 C6 . 1.514(4) ?
C6 C7 . 1.552(3) ?
C6 H2 . 0.93(3) ?
C7 C8 . 1.517(4) ?
C7 C10 . 1.548(4) ?
C7 Cl5 . 1.742(3) ?
C8 C9 . 1.319(4) ?
C8 Cl6 . 1.692(3) ?
C9 Cl4 . 1.688(3) ?
C10 Cl2 . 1.762(3) ?
C10 Cl1 . 1.769(3) ?
C11 N4 . 1.464(3) ?
C11 C12 . 1.515(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.507(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.375(4) ?
C13 C18 . 1.384(4) ?
C14 C15 . 1.366(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.357(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.357(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.382(5) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
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
C2 H1 O2 3_656 0.91(3) 2.50(3) 3.235(3) 138(2)
