#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/60/2206017.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_2206017
loop_
_publ_author_name
'McSweeney, Nigel'
'Pratt, Albert C.'
'Long, Conor'
'Howie, R. Alan'
_publ_section_title
;
 4',5',6',7'-Tetrachlorospiro[cyclohex-2-ene-1,2'-indan]-1',3'-dione
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1904
_journal_page_last               o1906
_journal_paper_doi               10.1107/S1600536805015904
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H8 Cl4 O2'
_chemical_formula_moiety         'C14 H8 Cl4 O2'
_chemical_formula_sum            'C14 H8 Cl4 O2'
_chemical_formula_weight         350.00
_chemical_melting_point          .401E-305
_chemical_name_systematic
;
4',5',6',7'-Tetrachlorospiro[cyclohex-2-ene-1,2'-indan]-1',3'-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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.25(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.707(6)
_cell_length_b                   12.103(8)
_cell_length_c                   10.800(6)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      10.6
_cell_measurement_theta_min      7.7
_cell_volume                     1399.2(14)
_computing_cell_refinement       'Nicolet P3 software'
_computing_data_collection       'Nicolet P3 software (Nicolet, 1980)'
_computing_data_reduction        'RDNIC (Howie, 1980)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nicolet P3 four-circle'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1632
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3222
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3222
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1410
_refine_ls_R_factor_gt           0.0704
_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)+(0.102P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1691
_refine_ls_wR_factor_ref         0.1977
_reflns_number_gt                1634
_reflns_number_total             3222
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6435.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206017
_cod_database_fobs_code          2206017
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_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
_atom_site_type_symbol
Cl1 0.42407(12) 0.27220(12) 0.56551(12) 0.0807(4) Uani d . 1 . . Cl
Cl2 0.26701(12) 0.39876(13) 0.36470(16) 0.0964(5) Uani d . 1 . . Cl
Cl3 0.39920(16) 0.53456(14) 0.16260(14) 0.1076(6) Uani d . 1 . . Cl
Cl4 0.68790(16) 0.54769(13) 0.15811(12) 0.0962(5) Uani d . 1 . . Cl
O1 0.9009(3) 0.4407(3) 0.3086(3) 0.0906(11) Uani d . 1 . . O
O2 0.7026(3) 0.2471(3) 0.6235(4) 0.0966(12) Uani d . 1 . . O
C1 0.8496(4) 0.3105(4) 0.4690(4) 0.0613(11) Uani d . 1 B . C
C2 0.8224(4) 0.3959(4) 0.3681(4) 0.0603(11) Uani d . 1 . . C
C3 0.6848(4) 0.4098(3) 0.3562(4) 0.0512(10) Uani d . 1 . . C
C4 0.6158(5) 0.4693(3) 0.2691(4) 0.0601(11) Uani d . 1 . . C
C5 0.4859(5) 0.4653(4) 0.2719(4) 0.0669(13) Uani d . 1 . . C
C6 0.4279(4) 0.4035(4) 0.3622(4) 0.0603(11) Uani d . 1 . . C
C7 0.4971(4) 0.3466(3) 0.4518(4) 0.0547(10) Uani d . 1 . . C
C8 0.6262(4) 0.3494(3) 0.4455(3) 0.0493(9) Uani d . 1 . . C
C9 0.7226(4) 0.2951(4) 0.5276(4) 0.0618(11) Uani d . 1 . . C
C10 0.9483(4) 0.3491(4) 0.5627(4) 0.0704(13) Uani d . 1 . . C
H10 0.9378 0.4171 0.6012 0.084 Uiso calc R 1 . . H
C11 1.0475(5) 0.2905(5) 0.5912(5) 0.0806(15) Uani d . 1 B . C
H11 1.1051 0.3211 0.6471 0.097 Uiso calc R 1 . . H
C12 1.0753(5) 0.1795(4) 0.5418(5) 0.0883(16) Uani d D 1 . . C
H12A 1.1062 0.1325 0.6085 0.106 Uiso calc PR 0.50 A 1 H
H12B 1.1401 0.1852 0.4807 0.106 Uiso calc PR 0.50 A 1 H
H12C 1.0471 0.1237 0.5993 0.106 Uiso calc PR 0.50 A 2 H
H12D 1.1649 0.1713 0.5337 0.106 Uiso calc PR 0.50 A 2 H
C13A 0.9592(9) 0.1280(8) 0.4827(10) 0.082(3) Uani d PD 0.50 B 1 C
H13A 0.9845 0.0660 0.4322 0.098 Uiso calc PR 0.50 B 1 H
H13B 0.9074 0.0992 0.5479 0.098 Uiso calc PR 0.50 B 1 H
C13B 1.0123(9) 0.1623(11) 0.4184(8) 0.080(3) Uani d PD 0.50 B 2 C
H13C 1.0615 0.1987 0.3560 0.096 Uiso calc PR 0.50 B 2 H
H13D 1.0126 0.0838 0.4001 0.096 Uiso calc PR 0.50 B 2 H
C14 0.8849(5) 0.2020(5) 0.4070(6) 0.101(2) Uani d D 1 . . C
H14A 0.8088 0.1640 0.3815 0.121 Uiso calc PR 0.50 B 1 H
H14B 0.9307 0.2187 0.3327 0.121 Uiso calc PR 0.50 B 1 H
H14C 0.8310 0.1449 0.4391 0.121 Uiso calc PR 0.50 B 2 H
H14D 0.8649 0.2091 0.3193 0.121 Uiso calc PR 0.50 B 2 H
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'
O O 0.0106 0.0060 '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_publ_flag
C10 C1 C9 112.0(4) y
C10 C1 C14 112.4(4) y
C9 C1 C14 108.0(4) y
C10 C1 C2 112.7(4) y
C9 C1 C2 102.8(3) y
C14 C1 C2 108.4(4) y
O1 C2 C3 127.4(5) ?
O1 C2 C1 124.4(4) ?
C3 C2 C1 108.2(4) ?
C8 C3 C4 120.5(4) ?
C8 C3 C2 110.3(4) ?
C4 C3 C2 129.1(4) ?
C3 C4 C5 119.1(4) ?
C3 C4 Cl4 121.2(4) ?
C5 C4 Cl4 119.8(4) ?
C6 C5 C4 119.8(4) ?
C6 C5 Cl3 120.4(4) ?
C4 C5 Cl3 119.8(4) ?
C5 C6 C7 121.2(4) ?
C5 C6 Cl2 119.5(4) ?
C7 C6 Cl2 119.3(4) ?
C8 C7 C6 118.1(4) ?
C8 C7 Cl1 121.1(3) ?
C6 C7 Cl1 120.8(4) ?
C3 C8 C7 121.3(4) ?
C3 C8 C9 109.2(4) ?
C7 C8 C9 129.4(4) ?
O2 C9 C8 125.8(4) ?
O2 C9 C1 126.2(4) ?
C8 C9 C1 108.1(4) ?
C11 C10 C1 122.6(4) ?
C11 C10 H10 118.7 ?
C1 C10 H10 118.7 ?
C10 C11 C12 125.2(5) ?
C10 C11 H11 117.4 ?
C12 C11 H11 117.4 ?
C11 C12 C13A 110.8(6) ?
C11 C12 C13B 111.0(6) ?
C11 C12 H12A 109.5 ?
C13A C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
C13A C12 H12B 109.5 ?
H12A C12 H12B 108.1 ?
C11 C12 H12C 109.4 ?
C13B C12 H12C 109.4 ?
C11 C12 H12D 109.4 ?
C13B C12 H12D 109.4 ?
H12C C12 H12D 108.0 ?
C14 C13A C12 114.8(7) y
C14 C13A H13A 108.6 ?
C12 C13A H13A 108.6 ?
C14 C13A H13B 108.6 ?
C12 C13A H13B 108.6 ?
H13A C13A H13B 107.5 ?
C14 C13B C12 115.8(7) y
C14 C13B H13C 108.3 ?
C12 C13B H13C 108.3 ?
C14 C13B H13D 108.3 ?
C12 C13B H13D 108.3 ?
H13C C13B H13D 107.4 ?
C13A C14 C1 115.1(6) y
C13B C14 C1 119.3(6) y
C13A C14 H14A 108.5 ?
C1 C14 H14A 108.5 ?
C13A C14 H14B 108.5 ?
C1 C14 H14B 108.5 ?
H14A C14 H14B 107.5 ?
C13B C14 H14C 107.5 ?
C1 C14 H14C 107.5 ?
C13B C14 H14D 107.5 ?
C1 C14 H14D 107.5 ?
H14C C14 H14D 107.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C7 1.724(4) ?
Cl2 C6 1.724(5) ?
Cl3 C5 1.706(5) ?
Cl4 C4 1.725(5) ?
O1 C2 1.199(5) ?
O2 C9 1.211(5) ?
C1 C10 1.521(6) y
C1 C9 1.524(6) y
C1 C14 1.525(6) y
C1 C2 1.525(6) y
C2 C3 1.485(6) ?
C3 C8 1.373(5) ?
C3 C4 1.386(6) ?
C4 C5 1.392(7) ?
C5 C6 1.386(7) ?
C6 C7 1.389(6) ?
C7 C8 1.386(6) ?
C8 C9 1.498(6) ?
C10 C11 1.308(7) ?
C10 H10 0.9300 ?
C11 C12 1.479(7) ?
C11 H11 0.9300 ?
C12 C13A 1.519(8) y
C12 C13B 1.495(8) y
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C12 H12C 0.9700 ?
C12 H12D 0.9700 ?
C13A C14 1.441(8) y
C13A H13A 0.9700 ?
C13A H13B 0.9700 ?
C13B C14 1.449(8) y
C13B H13C 0.9700 ?
C13B H13D 0.9700 ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C14 H14C 0.9700 ?
C14 H14D 0.9700 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C9 C1 C2 C3 -10.3(4) y
C1 C2 C3 C8 5.1(4) y
C2 C3 C8 C9 2.8(5) y
C3 C8 C9 C1 -9.6(5) y
C8 C9 C1 C2 11.9(4) y
C14 C1 C10 C11 -4.3(7) y
C1 C10 C11 C12 -2.4(9) y
C10 C11 C12 C13A -16.1(9) y
C10 C11 C12 C13B 25.4(9) y
C11 C12 C13A C14 42.8(11) ?
C11 C12 C13B C14 -42.1(12) ?
C12 C13A C14 C1 -51.8(11) ?
C12 C13B C14 C1 38.6(14) ?
C13A C14 C1 C10 31.2(8) y
C13B C14 C1 C10 -14.3(9) y
