 
data_JK832
 
_audit_creation_method            'SHELXL-2018/1'
_shelx_SHELXL_version_number      '2018/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety    'C7 H4 Cl4 O4' 
_chemical_formula_sum
 'C7 H4 Cl4 O4' 
_chemical_formula_weight          293.90
_chemical_compound_source   'Synthesized by Dr. Jiri Kaleta'

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'   0.3639   0.7018
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    12.3753(11)
_cell_length_b                    12.0364(11)
_cell_length_c                    21.8658(19)
_cell_angle_alpha                 90
_cell_angle_beta                  100.758(3)
_cell_angle_gamma                 90
_cell_volume                      3199.8(5)
_cell_formula_units_Z             12
_cell_measurement_temperature     200(2)
_cell_measurement_reflns_used     9635
_cell_measurement_theta_min       4.1160 
_cell_measurement_theta_max       72.5558 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.830          
_exptl_crystal_F_000              1752
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.319
_exptl_crystal_size_mid           0.199
_exptl_crystal_size_min           0.070
_exptl_absorpt_coefficient_mu     10.054
_shelx_estimated_absorpt_T_min    0.142
_shelx_estimated_absorpt_T_max    0.540
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.28 
_exptl_absorpt_correction_T_max   0.54
_exptl_absorpt_process_details    
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       200(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source                    'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator   'Helios Cu  multilayer optic'
_diffrn_measurement_device_type   'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             12643
_diffrn_reflns_av_unetI/netI      0.0479
_diffrn_reflns_av_R_equivalents   0.0504
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -26
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          4.116
_diffrn_reflns_theta_max          72.548
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.988
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.988
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.988
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              3145
_reflns_number_gt                 2847
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker Instrument Service vV6.2.9' 
_computing_cell_refinement        'SAINT V8.38A (Bruker AXS Inc., 2017)' 
_computing_data_reduction         'SAINT V8.38A (Bruker AXS Inc., 2017)' 
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0615P)²+9.5986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef        0.00093(12)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3145
_refine_ls_number_parameters      227
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0554
_refine_ls_R_factor_gt            0.0514
_refine_ls_wR_factor_ref          0.1360
_refine_ls_wR_factor_gt           0.1326
_refine_ls_goodness_of_fit_ref    1.038
_refine_ls_restrained_S_all       1.068
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl1 Cl 0.41923(6) 0.44197(6) 0.66614(4) 0.0422(2) Uani 1 1 d . . . . .
Cl2 Cl 0.29292(8) 0.34238(8) 0.56127(4) 0.0532(3) Uani 1 1 d . . . . .
Cl3 Cl 0.13674(7) 0.13603(7) 0.71664(5) 0.0531(3) Uani 1 1 d . . . . .
Cl4 Cl 0.13194(7) 0.17099(8) 0.58956(4) 0.0553(3) Uani 1 1 d . . . . .
O1 O 0.1538(2) 0.5246(2) 0.66302(15) 0.0597(7) Uani 1 1 d . . . . .
H1 H 0.112837 0.577478 0.664383 0.072 Uiso 1 1 d R U . . .
O2 O 0.0362(2) 0.3958(2) 0.68363(17) 0.0645(8) Uani 1 1 d . . . . .
O3 O 0.38238(19) 0.04413(18) 0.68685(14) 0.0528(7) Uani 1 1 d . . . . .
H3 H 0.431130 -0.003622 0.682354 0.063 Uiso 1 1 d R U . . .
O4 O 0.50369(18) 0.17395(18) 0.67219(13) 0.0474(6) Uani 1 1 d . . . . .
C1 C 0.2159(2) 0.3414(2) 0.67828(14) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.3143(2) 0.3409(2) 0.64298(13) 0.0307(6) Uani 1 1 d . . . . .
C3 C 0.3254(2) 0.2299(2) 0.67989(13) 0.0274(6) Uani 1 1 d . . . . .
C4 C 0.1980(2) 0.2154(2) 0.66357(14) 0.0329(6) Uani 1 1 d . . . . .
C5 C 0.3025(2) 0.3022(2) 0.73640(14) 0.0334(6) Uani 1 1 d . . . . .
H5A H 0.272734 0.261899 0.769069 0.040 Uiso 1 1 calc R U . . .
H5B H 0.360133 0.356810 0.753481 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1275(2) 0.4272(2) 0.67488(15) 0.0352(7) Uani 1 1 d . . . . .
C7 C 0.4110(2) 0.1428(2) 0.67908(14) 0.0308(6) Uani 1 1 d . . . . .
Cl1D Cl 0.7872(3) 0.1722(3) 0.38966(10) 0.0800(9) Uani 0.5 1 d . . P . .
Cl2D Cl 0.88821(16) 0.09667(15) 0.50611(10) 0.0581(5) Uani 0.5 1 d . . P . .
Cl3D Cl 0.8436(2) 0.12479(19) 0.42048(18) 0.0768(8) Uani 0.5 1 d . . P . .
Cl4D Cl 0.68070(17) 0.28520(16) 0.38596(8) 0.0551(5) Uani 0.5 1 d . . P . .
O1D O 0.6095(3) 0.0267(3) 0.46537(16) 0.0747(10) Uani 1 1 d . . . . .
H2D H 0.552377 -0.018705 0.459922 0.090 Uiso 1 1 d R U . . .
O2D O 0.5352(3) 0.1306(3) 0.53106(16) 0.0759(10) Uani 1 1 d . . . . .
C1D C 0.6923(4) 0.1984(4) 0.4983(2) 0.0687(14) Uani 1 1 d D . . . .
C2D C 0.7752(4) 0.2098(4) 0.4606(3) 0.0832(18) Uani 1 1 d . . . . .
C4D C 0.6729(6) 0.3166(6) 0.4562(5) 0.064(2) Uani 0.5 1 d D . P . .
H4D H 0.665331 0.310378 0.410295 0.077 Uiso 0.5 1 d R U P . .
H4E H 0.624937 0.373377 0.470109 0.077 Uiso 0.5 1 d R U P . .
C6D C 0.6052(3) 0.1106(3) 0.49793(18) 0.0545(10) Uani 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Cl1 C2 1.782(3) . ?
Cl2 C2 1.757(3) . ?
Cl3 C4 1.778(3) . ?
Cl4 C4 1.755(3) . ?
O1 C6 1.256(4) . ?
O1 H1 0.8177 . ?
O2 C6 1.240(4) . ?
O3 C7 1.259(4) . ?
O3 H3 0.8521 . ?
O4 C7 1.243(4) . ?
C1 C6 1.496(3) . ?
C1 C4 1.558(4) . ?
C1 C2 1.559(4) . ?
C1 C5 1.574(4) . ?
C1 C3 1.902(4) . ?
C2 C3 1.554(4) . ?
C3 C7 1.494(3) . ?
C3 C4 1.559(4) . ?
C3 C5 1.579(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
Cl1D Cl3D 1.045(4) . ?
Cl1D C2D 1.648(5) . ?
Cl1D Cl4D 1.885(5) . ?
Cl2D C4D 1.605(11) 7_656 ?
Cl2D Cl3D 1.881(5) . ?
Cl2D C2D 2.069(7) . ?
Cl2D H4E 0.677(12) 7_656 ?
Cl3D C2D 1.676(5) . ?
Cl4D C4D 1.601(11) . ?
Cl4D C2D 2.035(7) . ?
Cl4D H4D 0.6701 . ?
O1D C6D 1.242(5) . ?
O1D H2D 0.8838 . ?
O2D C6D 1.252(5) . ?
C1D C2D 1.435(5) 7_656 ?
C1D C2D 1.438(5) . ?
C1D C6D 1.509(4) . ?
C1D C4D 1.687(7) . ?
C1D C4D 1.786(9) 7_656 ?
C1D C1D 1.884(7) 7_656 ?
C2D C4D 1.794(11) . ?
C2D C4D 1.842(11) 7_656 ?
C4D H4D 0.9926 . ?
C4D H4E 0.9900 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C6 O1 H1 122.2 . . ?
C7 O3 H3 113.4 . . ?
C6 C1 C4 126.0(2) . . ?
C6 C1 C2 127.5(3) . . ?
C4 C1 C2 89.3(2) . . ?
C6 C1 C5 128.9(2) . . ?
C4 C1 C5 85.6(2) . . ?
C2 C1 C5 85.5(2) . . ?
C6 C1 C3 177.9(2) . . ?
C4 C1 C3 52.43(15) . . ?
C2 C1 C3 52.21(15) . . ?
C5 C1 C3 53.02(15) . . ?
C3 C2 C1 75.35(19) . . ?
C3 C2 Cl2 121.2(2) . . ?
C1 C2 Cl2 121.4(2) . . ?
C3 C2 Cl1 116.76(19) . . ?
C1 C2 Cl1 116.9(2) . . ?
Cl2 C2 Cl1 104.21(16) . . ?
C7 C3 C2 126.3(2) . . ?
C7 C3 C4 127.4(2) . . ?
C2 C3 C4 89.5(2) . . ?
C7 C3 C5 128.8(2) . . ?
C2 C3 C5 85.5(2) . . ?
C4 C3 C5 85.4(2) . . ?
C7 C3 C1 178.3(2) . . ?
C2 C3 C1 52.44(15) . . ?
C4 C3 C1 52.35(15) . . ?
C5 C3 C1 52.79(15) . . ?
C1 C4 C3 75.22(19) . . ?
C1 C4 Cl4 120.7(2) . . ?
C3 C4 Cl4 121.5(2) . . ?
C1 C4 Cl3 116.7(2) . . ?
C3 C4 Cl3 116.5(2) . . ?
Cl4 C4 Cl3 104.85(16) . . ?
C1 C5 C3 74.20(19) . . ?
C1 C5 H5A 116.1 . . ?
C3 C5 H5A 116.1 . . ?
C1 C5 H5B 116.1 . . ?
C3 C5 H5B 116.1 . . ?
H5A C5 H5B 113.1 . . ?
O2 C6 O1 126.5(3) . . ?
O2 C6 C1 117.4(3) . . ?
O1 C6 C1 116.1(3) . . ?
O4 C7 O3 126.2(2) . . ?
O4 C7 C3 117.5(3) . . ?
O3 C7 C3 116.3(3) . . ?
Cl3D Cl1D C2D 73.1(3) . . ?
Cl3D Cl1D Cl4D 143.1(3) . . ?
C2D Cl1D Cl4D 70.0(3) . . ?
C4D Cl2D Cl3D 108.4(3) 7_656 . ?
C4D Cl2D C2D 58.6(3) 7_656 . ?
Cl3D Cl2D C2D 49.93(15) . . ?
C4D Cl2D H4E 19.1(4) 7_656 7_656 ?
Cl3D Cl2D H4E 126.9(6) . 7_656 ?
C2D Cl2D H4E 77.4(6) . 7_656 ?
Cl1D Cl3D C2D 70.2(3) . . ?
Cl1D Cl3D Cl2D 140.9(3) . . ?
C2D Cl3D Cl2D 70.9(3) . . ?
C4D Cl4D Cl1D 107.2(3) . . ?
C4D Cl4D C2D 57.7(3) . . ?
Cl1D Cl4D C2D 49.54(14) . . ?
C4D Cl4D H4D 19.1 . . ?
Cl1D Cl4D H4D 126.3 . . ?
C2D Cl4D H4D 76.8 . . ?
C6D O1D H2D 117.5 . . ?
C2D C1D C2D 98.0(3) 7_656 . ?
C2D C1D C6D 131.3(4) 7_656 . ?
C2D C1D C6D 130.5(4) . . ?
C2D C1D C4D 71.8(5) 7_656 . ?
C2D C1D C4D 69.6(5) . . ?
C6D C1D C4D 124.0(4) . . ?
C2D C1D C4D 66.7(4) 7_656 7_656 ?
C2D C1D C4D 68.7(4) . 7_656 ?
C6D C1D C4D 121.6(5) . 7_656 ?
C4D C1D C4D 114.4(3) . 7_656 ?
C2D C1D C1D 49.1(2) 7_656 7_656 ?
C2D C1D C1D 49.0(2) . 7_656 ?
C6D C1D C1D 176.3(6) . 7_656 ?
C4D C1D C1D 59.7(4) . 7_656 ?
C4D C1D C1D 54.7(3) 7_656 7_656 ?
C1D C2D C1D 82.0(3) 7_656 . ?
C1D C2D Cl1D 137.5(3) 7_656 . ?
C1D C2D Cl1D 135.5(4) . . ?
C1D C2D Cl3D 133.5(4) 7_656 . ?
C1D C2D Cl3D 136.6(4) . . ?
Cl1D C2D Cl3D 36.64(16) . . ?
C1D C2D C4D 66.0(4) 7_656 . ?
C1D C2D C4D 61.8(4) . . ?
Cl1D C2D C4D 109.4(5) . . ?
Cl3D C2D C4D 146.1(5) . . ?
C1D C2D C4D 60.5(4) 7_656 7_656 ?
C1D C2D C4D 64.6(4) . 7_656 ?
Cl1D C2D C4D 143.8(5) . 7_656 ?
Cl3D C2D C4D 107.1(5) . 7_656 ?
C4D C2D C4D 106.8(3) . 7_656 ?
C1D C2D Cl4D 102.2(4) 7_656 . ?
C1D C2D Cl4D 97.9(4) . . ?
Cl1D C2D Cl4D 60.5(3) . . ?
Cl3D C2D Cl4D 97.1(3) . . ?
C4D C2D Cl4D 48.9(4) . . ?
C4D C2D Cl4D 155.7(4) 7_656 . ?
C1D C2D Cl2D 96.9(4) 7_656 . ?
C1D C2D Cl2D 98.7(4) . . ?
Cl1D C2D Cl2D 95.8(3) . . ?
Cl3D C2D Cl2D 59.2(3) . . ?
C4D C2D Cl2D 154.7(4) . . ?
C4D C2D Cl2D 48.0(4) 7_656 . ?
Cl4D C2D Cl2D 156.2(2) . . ?
Cl4D C4D Cl2D 139.9(5) . 7_656 ?
Cl4D C4D C1D 107.2(6) . . ?
Cl2D C4D C1D 107.5(6) 7_656 . ?
Cl4D C4D C1D 107.1(6) . 7_656 ?
Cl2D C4D C1D 105.1(5) 7_656 7_656 ?
C1D C4D C1D 65.6(3) . 7_656 ?
Cl4D C4D C2D 73.4(5) . . ?
Cl2D C4D C2D 146.5(6) 7_656 . ?
C1D C4D C2D 48.7(3) . . ?
C1D C4D C2D 47.3(3) 7_656 . ?
Cl4D C4D C2D 146.6(6) . 7_656 ?
Cl2D C4D C2D 73.4(5) 7_656 7_656 ?
C1D C4D C2D 47.7(3) . 7_656 ?
C1D C4D C2D 46.7(3) 7_656 7_656 ?
C2D C4D C2D 73.2(3) . 7_656 ?
Cl4D C4D H4D 12.8 . . ?
Cl2D C4D H4D 127.1 7_656 . ?
C1D C4D H4D 117.7 . . ?
C1D C4D H4D 117.3 7_656 . ?
C2D C4D H4D 86.1 . . ?
C2D C4D H4D 159.4 7_656 . ?
Cl4D C4D H4E 127.2 . . ?
Cl2D C4D H4E 12.9 7_656 . ?
C1D C4D H4E 116.5 . . ?
C1D C4D H4E 116.7 7_656 . ?
C2D C4D H4E 159.4 . . ?
C2D C4D H4E 86.2 7_656 . ?
H4D C4D H4E 114.5 . . ?
O1D C6D O2D 126.6(3) . . ?
O1D C6D C1D 117.7(3) . . ?
O2D C6D C1D 115.7(3) . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
 _geom_hbond_publ_flag
O1 H1 O4  0.82 1.81 2.619(3) 168.4 3_455 yes
O3 H3 O2  0.85 1.77 2.620(3) 172.6 3_545 yes
O1D H2D O2D  0.88 1.76 2.617(3) 161.9 5_656 yes
 
_refine_diff_density_max    0.775
_refine_diff_density_min   -0.502
_refine_diff_density_rms    0.085



