#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/60/2006077.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_2006077
loop_
_publ_author_name
'Bartkowska, B.'
'Bohnen, F. M.'
'Krüger, C.'
'Maier, W. F.'
_publ_section_title
;4-(1,7,8,9,10,10-Hexachloro-3,5-dioxo-4-azatricyclo[5.2.1.0^2,6^]dec-8-en-4-yl)butyric
 Acid Toluene Solvate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              521
_journal_page_last               522
_journal_paper_doi               10.1107/S0108270196015569
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          'C13 H9 Cl6 N O4, C7 H8'
_chemical_formula_moiety         'C13 H9 Cl6 N O4,C7 H8'
_chemical_formula_structural     'C13 H9 Cl6 N O4 * C7 H8'
_chemical_formula_sum            'C20 H17 Cl6 N O4'
_chemical_formula_weight         547.88
_chemical_melting_point          394
_chemical_name_systematic
;
 4-(1,7,8,9,10,10-Hexachloro-3,5-dioxo-4-aza-tricyclo-[5.2.1.0^2,6^]dec-8-
 en-4-yl-butyracid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                105.084(11)
_cell_angle_beta                 104.568(12)
_cell_angle_gamma                97.278(10)
_cell_formula_units_Z            2
_cell_length_a                   8.766(2)
_cell_length_b                   10.759(2)
_cell_length_c                   13.158(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      22.53
_cell_measurement_theta_min      15.16
_cell_volume                     1134.9(4)
_computing_cell_refinement       'CAD-4 software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
'DATAP (Coppens, Leiserowitz & Rabinovich, 1965)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and XANADU (Roberts & Sheldrick, 1975)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5160
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  30
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    none
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.435
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.134
_refine_ls_goodness_of_fit_obs   1.159
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_restrained_S_obs      1.159
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_obs          0.0337
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.056P)²+1.132P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1104
_refine_ls_wR_factor_obs         0.1090
_reflns_number_observed          4838
_reflns_number_total             5160
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            na1268.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (26
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (7
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (42
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (11 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.056P)^2^+1.132P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.056P)^2^+1.132P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1134.9(3)
_cod_database_code               2006077
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_type_symbol
C1 1 0.8847(3) 0.8765(2) 0.3586(2) 0.0196(4) Uani d C
C2 1 0.7935(3) 0.7902(2) 0.2443(2) 0.0203(4) Uani d C
C3 1 0.6500(2) 0.6894(2) 0.2372(2) 0.0194(4) Uani d C
C4 1 0.7047(2) 0.5812(2) 0.2845(2) 0.0187(4) Uani d C
C5 1 0.4837(2) 0.5007(2) 0.3539(2) 0.0160(4) Uani d C
C6 1 0.3471(2) 0.3819(2) 0.3185(2) 0.0144(3) Uani d C
C7 1 0.1778(2) 0.4166(2) 0.2895(2) 0.0147(4) Uani d C
C8 1 0.1795(2) 0.5052(2) 0.2150(2) 0.0154(4) Uani d C
C9 1 0.1884(2) 0.4317(2) 0.1195(2) 0.0146(3) Uani d C
C10 1 0.1899(2) 0.2931(2) 0.1256(2) 0.0139(3) Uani d C
C11 1 0.3553(2) 0.2970(2) 0.2063(2) 0.0142(3) Uani d C
C12 1 0.4980(2) 0.3713(2) 0.1855(2) 0.0159(4) Uani d C
C13 1 0.0781(2) 0.2866(2) 0.2003(2) 0.0145(3) Uani d C
C14 1 0.4809(3) -0.0058(2) 0.2192(2) 0.0246(4) Uani d C
C15 1 0.6269(3) 0.0774(2) 0.2376(2) 0.0258(4) Uani d C
C16 1 0.7033(3) 0.1705(2) 0.3385(2) 0.0309(5) Uani d C
C17 1 0.6348(3) 0.1827(3) 0.4239(2) 0.0329(5) Uani d C
C18 1 0.4896(3) 0.1009(3) 0.4073(2) 0.0315(5) Uani d C
C19 1 0.4139(3) 0.0066(2) 0.3056(2) 0.0278(5) Uani d C
C20 1 0.3938(4) -0.1032(3) 0.1080(3) 0.0412(7) Uani d C
H1O 1 1.0643(44) 0.9900(36) 0.4305(31) 0.046(10) Uiso d H
H2A 1 0.7608(34) 0.8489(28) 0.2046(23) 0.022(6) Uiso d H
H2B 1 0.8724(38) 0.7480(30) 0.2105(25) 0.032(8) Uiso d H
H3A 1 0.5918(35) 0.6489(28) 0.1622(24) 0.025(7) Uiso d H
H3B 1 0.5867(37) 0.7320(30) 0.2773(25) 0.030(7) Uiso d H
H4A 1 0.7686(35) 0.6167(28) 0.3641(24) 0.027(7) Uiso d H
H4B 1 0.7724(29) 0.5330(23) 0.2437(19) 0.010(5) Uiso d H
H6A 1 0.3564(33) 0.3407(27) 0.3731(22) 0.022(6) Uiso d H
H11A 1 0.3692(32) 0.2094(26) 0.2066(21) 0.018(6) Uiso d H
H15 1 0.6643(33) 0.0650(26) 0.1760(23) 0.021(6) Uiso d H
H16 1 0.8076(41) 0.2289(32) 0.3517(26) 0.037(8) Uiso d H
H17 1 0.6824(42) 0.2498(34) 0.4932(28) 0.043(9) Uiso d H
H18 1 0.4481(43) 0.1076(34) 0.4659(29) 0.044(9) Uiso d H
H19 1 0.3182(41) -0.0478(33) 0.2973(27) 0.038(8) Uiso d H
H20A 1 0.4632(73) -0.1112(56) 0.0661(47) 0.103(19) Uiso d H
H20B 1 0.3478(72) -0.1823(60) 0.1120(46) 0.104(18) Uiso d H
H20C 1 0.3323(81) -0.0552(65) 0.0725(53) 0.124(22) Uiso d H
Cl1 1 0.10378(6) 0.47231(5) 0.40131(4) 0.02201(12) Uani d Cl
Cl2 1 0.13118(6) 0.16665(5) 0.00015(4) 0.02131(12) Uani d Cl
Cl3 1 0.07656(6) 0.14816(5) 0.24837(4) 0.01905(12) Uani d Cl
Cl4 1 0.18720(6) 0.66898(5) 0.25787(4) 0.02307(13) Uani d Cl
Cl5 1 -0.12197(5) 0.29475(5) 0.13998(4) 0.01911(12) Uani d Cl
Cl6 1 0.21378(6) 0.48343(5) 0.01197(4) 0.02226(13) Uani d Cl
N 1 0.5671(2) 0.4825(2) 0.27590(14) 0.0169(3) Uani d N
O1 1 0.8315(2) 0.8877(2) 0.43729(14) 0.0286(4) Uani d O
O2 1 1.0278(2) 0.9405(2) 0.36525(14) 0.0262(3) Uani d O
O3 1 0.5162(2) 0.59639(14) 0.43320(12) 0.0207(3) Uani d O
O4 1 0.5435(2) 0.3425(2) 0.10472(13) 0.0217(3) Uani d O
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'
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'
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
O1 C1 O2 123.6(2) n
O1 C1 C2 123.4(2) n
O2 C1 C2 113.0(2) n
C1 C2 C3 114.8(2) n
C2 C3 C4 111.1(2) n
N C4 C3 111.3(2) y
O3 C5 N 124.3(2) y
O3 C5 C6 127.8(2) y
N C5 C6 107.8(2) y
C5 C6 C11 104.9(2) n
C5 C6 C7 113.0(2) n
C11 C6 C7 103.25(14) y
C8 C7 C13 98.75(15) n
C8 C7 C6 107.34(15) n
C13 C7 C6 100.79(14) n
C8 C7 Cl1 116.08(14) n
C13 C7 Cl1 116.09(13) n
C6 C7 Cl1 115.51(13) n
C9 C8 C7 107.3(2) n
C9 C8 Cl4 128.8(2) n
C7 C8 Cl4 123.65(14) n
C8 C9 C10 108.2(2) n
C8 C9 Cl6 127.1(2) n
C10 C9 Cl6 124.39(15) n
C9 C10 C11 107.14(15) n
C9 C10 C13 99.31(15) n
C11 C10 C13 100.64(14) n
C9 C10 Cl2 116.90(14) n
C11 C10 Cl2 115.47(13) n
C13 C10 Cl2 115.05(13) n
C12 C11 C6 105.1(2) n
C12 C11 C10 113.7(2) n
C6 C11 C10 103.20(14) n
O4 C12 N 125.0(2) y
O4 C12 C11 127.3(2) y
N C12 C11 107.7(2) y
C7 C13 C10 92.80(14) n
C7 C13 Cl5 113.40(13) n
C10 C13 Cl5 114.32(13) n
C7 C13 Cl3 113.56(13) n
C10 C13 Cl3 113.73(13) n
Cl5 C13 Cl3 108.53(10) n
C19 C14 C15 118.3(2) n
C19 C14 C20 120.4(2) n
C15 C14 C20 121.3(2) n
C16 C15 C14 121.2(2) n
C15 C16 C17 120.1(2) n
C18 C17 C16 119.6(2) n
C17 C18 C19 120.0(2) n
C14 C19 C18 120.8(2) n
C12 N C5 114.2(2) y
C12 N C4 123.8(2) y
C5 N C4 121.7(2) y
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 O1 . 1.224(3) y
C1 O2 . 1.322(3) y
C1 C2 . 1.498(3) y
C2 C3 . 1.519(3) y
C3 C4 . 1.531(3) y
C4 N . 1.463(2) y
C5 O3 . 1.203(2) y
C5 N . 1.391(3) y
C5 C6 . 1.519(3) y
C6 C11 . 1.545(3) y
C6 C7 . 1.555(3) y
C7 C8 . 1.536(3) y
C7 C13 . 1.555(3) y
C7 Cl1 . 1.750(2) y
C8 C9 . 1.325(3) y
C8 Cl4 . 1.692(2) y
C9 C10 . 1.515(3) y
C9 Cl6 . 1.703(2) y
C10 C11 . 1.555(3) y
C10 C13 . 1.561(3) y
C10 Cl2 . 1.751(2) y
C11 C12 . 1.520(3) y
C12 O4 . 1.207(3) y
C12 N . 1.388(2) y
C13 Cl5 . 1.758(2) y
C13 Cl3 . 1.763(2) y
C14 C19 . 1.390(4) n
C14 C15 . 1.392(3) n
C14 C20 . 1.504(3) n
C15 C16 . 1.381(4) n
C16 C17 . 1.386(4) n
C17 C18 . 1.386(4) n
C18 C19 . 1.392(4) n
