#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$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.'
'Kr\"uger, 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       \w-2\q
_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/[\s^2^(Fo^2^)+(0.056P)^2^+1.132P] where P = (Fo^2^+2Fc^2^)/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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
C1 0.0214(10) 0.0014(7) 0.0099(8) 0.0151(9) 0.0069(8) 0.0240(10)
C2 0.0206(10) 0.0031(8) 0.0091(8) 0.0187(9) 0.0065(8) 0.0228(10)
C3 0.0159(9) 0.0024(7) 0.0058(8) 0.0186(9) 0.0038(8) 0.0221(10)
C4 0.0123(8) 0.0004(7) 0.0048(8) 0.0164(9) 0.0059(8) 0.0259(10)
C5 0.0132(8) 0.0026(7) 0.0019(7) 0.0168(9) 0.0057(7) 0.0167(9)
C6 0.0127(8) 0.0025(7) 0.0030(7) 0.0153(8) 0.0049(7) 0.0148(9)
C7 0.0136(8) 0.0028(7) 0.0067(7) 0.0152(8) 0.0029(7) 0.0155(9)
C8 0.0112(8) 0.0021(6) 0.0032(7) 0.0135(8) 0.0052(7) 0.0206(9)
C9 0.0131(8) 0.0017(7) 0.0030(7) 0.0162(9) 0.0097(7) 0.0161(9)
C10 0.0136(8) 0.0009(6) 0.0032(7) 0.0127(8) 0.0026(7) 0.0135(8)
C11 0.0122(8) 0.0031(7) 0.0037(7) 0.0148(8) 0.0053(7) 0.0158(9)
C12 0.0113(8) 0.0037(7) 0.0034(7) 0.0145(8) 0.0056(7) 0.0215(9)
C13 0.0113(8) 0.0014(7) 0.0031(7) 0.0151(8) 0.0065(7) 0.0170(9)
C14 0.0253(11) 0.0071(8) 0.0015(9) 0.0179(10) 0.0050(8) 0.0268(11)
C15 0.0260(11) 0.0082(9) 0.0147(9) 0.0231(11) 0.0085(9) 0.0326(12)
C16 0.0214(11) 0.0028(9) 0.0075(10) 0.0258(11) 0.0046(10) 0.0407(14)
C17 0.0337(13) 0.0078(10) 0.0038(10) 0.0268(12) -0.0017(10) 0.0294(12)
C18 0.0391(13) 0.0146(10) 0.0206(11) 0.0303(12) 0.0128(10) 0.0346(13)
C19 0.0239(11) 0.0057(8) 0.0126(10) 0.0199(10) 0.0128(9) 0.0435(14)
C20 0.046(2) 0.0052(12) -0.0030(12) 0.0287(13) -0.0006(11) 0.0336(14)
Cl1 0.0213(2) 0.0052(2) 0.0110(2) 0.0260(3) 0.0029(2) 0.0193(2)
Cl2 0.0231(2) -0.0004(2) 0.0043(2) 0.0188(2) -0.0011(2) 0.0160(2)
Cl3 0.0173(2) 0.0015(2) 0.0070(2) 0.0170(2) 0.0105(2) 0.0250(2)
Cl4 0.0262(3) 0.0061(2) 0.0060(2) 0.0139(2) 0.0045(2) 0.0275(3)
Cl5 0.0107(2) 0.0016(2) 0.0026(2) 0.0217(2) 0.0077(2) 0.0236(2)
Cl6 0.0263(3) 0.0039(2) 0.0074(2) 0.0241(3) 0.0111(2) 0.0190(2)
N 0.0129(7) 0.0007(6) 0.0040(6) 0.0163(8) 0.0038(6) 0.0196(8)
O1 0.0296(8) -0.0066(7) 0.0155(7) 0.0267(8) 0.0010(6) 0.0259(8)
O2 0.0244(8) -0.0060(6) 0.0123(7) 0.0251(8) 0.0017(7) 0.0253(8)
O3 0.0216(7) 0.0012(6) 0.0028(6) 0.0194(7) 0.0024(6) 0.0167(7)
O4 0.0177(7) 0.0041(6) 0.0108(6) 0.0246(7) 0.0040(6) 0.0233(7)
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
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139055464