 
data_JK769-01
 
_audit_creation_method            'SHELXL-2018/1'
_shelx_SHELXL_version_number      '2018/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety      'C9 H10 Cl2 O4'
_chemical_formula_sum
 'C9 H10 Cl2 O4' 
_chemical_formula_weight          253.07
_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'   0.0033   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'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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'
 
_cell_length_a                    7.2292(4)
_cell_length_b                    8.9578(5)
_cell_length_c                    9.7870(5)
_cell_angle_alpha                 103.405(2)
_cell_angle_beta                  109.383(2)
_cell_angle_gamma                 103.080(2)
_cell_volume                      548.90(5)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     9956 
_cell_measurement_theta_min       2.4765 
_cell_measurement_theta_max       27.5166 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.531          
_exptl_crystal_F_000              260
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.337
_exptl_crystal_size_mid           0.195
_exptl_crystal_size_min           0.154
_exptl_absorpt_coefficient_mu     0.581
_shelx_estimated_absorpt_T_min    0.828
_shelx_estimated_absorpt_T_max    0.916
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.86 
_exptl_absorpt_correction_T_max   0.92 
_exptl_absorpt_process_details    
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'I\mS  micro-focus sealed tube' 
_diffrn_radiation_monochromator   'Quazar Mo 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             14837
_diffrn_reflns_av_unetI/netI      0.0165
_diffrn_reflns_av_R_equivalents   0.0240
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.340
_diffrn_reflns_theta_max          27.516
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              2515
_reflns_number_gt                 2322
_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 vV6.2.4' 
_computing_cell_refinement        'SAINT V8.37A (Bruker AXS Inc., 2015)' 
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)' 
_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)+(0.0311P)²+0.3242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2515
_refine_ls_number_parameters      138
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0311
_refine_ls_R_factor_gt            0.0280
_refine_ls_wR_factor_ref          0.0719
_refine_ls_wR_factor_gt           0.0703
_refine_ls_goodness_of_fit_ref    1.076
_refine_ls_restrained_S_all       1.076
_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 0.79233(5) 0.17029(4) 0.23749(4) 0.02138(10) Uani 1 1 d . . . . .
Cl2 Cl 0.70989(6) 0.29771(5) 0.49822(4) 0.02846(11) Uani 1 1 d . . . . .
O1 O 0.67061(17) 0.65160(12) 0.35852(12) 0.0252(2) Uani 1 1 d . . . . .
O2 O 0.7688(2) 0.56220(14) 0.16912(15) 0.0380(3) Uani 1 1 d . . . . .
O3 O 0.33487(15) -0.11249(12) 0.16000(13) 0.0242(2) Uani 1 1 d . . . . .
O4 O 0.0738(2) -0.02801(15) 0.1772(2) 0.0585(5) Uani 1 1 d . . . . .
C1 C 0.5389(2) 0.37353(15) 0.22496(15) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.6158(2) 0.24858(15) 0.29520(15) 0.0160(3) Uani 1 1 d . . . . .
C3 C 0.3783(2) 0.16319(15) 0.20025(15) 0.0164(3) Uani 1 1 d . . . . .
C4 C 0.3499(2) 0.32744(16) 0.26849(17) 0.0198(3) Uani 1 1 d . . . . .
H4A H 0.381372 0.361808 0.379725 0.024 Uiso 1 1 calc R U . . .
H4B H 0.222628 0.345195 0.206532 0.024 Uiso 1 1 calc R U . . .
C5 C 0.4098(2) 0.22868(16) 0.07162(15) 0.0186(3) Uani 1 1 d . . . . .
H5A H 0.490495 0.181045 0.020539 0.022 Uiso 1 1 calc R U . . .
H5B H 0.285958 0.241226 -0.001109 0.022 Uiso 1 1 calc R U . . .
C6 C 0.6733(2) 0.53791(16) 0.24565(16) 0.0182(3) Uani 1 1 d . . . . .
C7 C 0.2443(2) -0.00146(16) 0.17897(16) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.7924(3) 0.81784(17) 0.38905(19) 0.0284(3) Uani 1 1 d . . . . .
H8A H 0.935982 0.824361 0.406573 0.043 Uiso 1 1 calc R U . . .
H8B H 0.790349 0.889519 0.480530 0.043 Uiso 1 1 calc R U . . .
H8C H 0.732978 0.851864 0.300674 0.043 Uiso 1 1 calc R U . . .
C9 C 0.2111(2) -0.27909(17) 0.12592(18) 0.0245(3) Uani 1 1 d . . . . .
H9A H 0.114469 -0.279965 0.176382 0.037 Uiso 1 1 calc R U . . .
H9B H 0.302785 -0.339406 0.163791 0.037 Uiso 1 1 calc R U . . .
H9C H 0.132483 -0.330425 0.014563 0.037 Uiso 1 1 calc R U . . .
 
 
_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 1.7719(13) . ?
Cl2 C2 1.7794(13) . ?
O1 C6 1.3263(17) . ?
O1 C8 1.4517(17) . ?
O2 C6 1.1984(17) . ?
O3 C7 1.3200(17) . ?
O3 C9 1.4511(16) . ?
O4 C7 1.1949(18) . ?
C1 C6 1.4956(17) . ?
C1 C2 1.5554(18) . ?
C1 C5 1.5576(18) . ?
C1 C4 1.5592(18) . ?
C1 C3 1.8890(18) . ?
C2 C3 1.5532(17) . ?
C3 C7 1.4949(18) . ?
C3 C4 1.5575(18) . ?
C3 C5 1.5660(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
 
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 C8 116.55(11) . . ?
C7 O3 C9 116.55(11) . . ?
C6 C1 C2 125.45(11) . . ?
C6 C1 C5 127.10(11) . . ?
C2 C1 C5 86.78(9) . . ?
C6 C1 C4 129.23(11) . . ?
C2 C1 C4 87.38(9) . . ?
C5 C1 C4 87.19(10) . . ?
C6 C1 C3 177.75(11) . . ?
C2 C1 C3 52.53(7) . . ?
C5 C1 C3 52.99(7) . . ?
C4 C1 C3 52.65(7) . . ?
C3 C2 C1 74.84(9) . . ?
C3 C2 Cl1 119.62(9) . . ?
C1 C2 Cl1 118.05(9) . . ?
C3 C2 Cl2 117.43(9) . . ?
C1 C2 Cl2 117.83(9) . . ?
Cl1 C2 Cl2 106.87(7) . . ?
C7 C3 C2 129.35(11) . . ?
C7 C3 C4 125.62(11) . . ?
C2 C3 C4 87.52(9) . . ?
C7 C3 C5 127.04(11) . . ?
C2 C3 C5 86.57(9) . . ?
C4 C3 C5 86.96(10) . . ?
C7 C3 C1 177.88(11) . . ?
C2 C3 C1 52.63(7) . . ?
C4 C3 C1 52.73(7) . . ?
C5 C3 C1 52.59(7) . . ?
C3 C4 C1 74.62(9) . . ?
C3 C4 H4A 116.0 . . ?
C1 C4 H4A 116.0 . . ?
C3 C4 H4B 116.0 . . ?
C1 C4 H4B 116.0 . . ?
H4A C4 H4B 113.0 . . ?
C1 C5 C3 74.42(9) . . ?
C1 C5 H5A 116.1 . . ?
C3 C5 H5A 116.1 . . ?
C1 C5 H5B 116.1 . . ?
C3 C5 H5B 116.1 . . ?
H5A C5 H5B 113.0 . . ?
O2 C6 O1 125.11(12) . . ?
O2 C6 C1 124.01(13) . . ?
O1 C6 C1 110.89(11) . . ?
O4 C7 O3 124.63(13) . . ?
O4 C7 C3 123.17(13) . . ?
O3 C7 C3 112.19(11) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
 
_refine_diff_density_max    0.433
_refine_diff_density_min   -0.305
_refine_diff_density_rms    0.052



