 
data_4b
  
_audit_creation_method            'SHELXL-2017/1' 
_shelx_SHELXL_version_number      '2017/1' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C16 H16 Cl2 O4' 
_chemical_formula_sum 
 'C16 H16 Cl2 O4' 
_chemical_formula_weight          343.19 
  
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       monoclinic 
_space_group_IT_number            13 
_space_group_name_H-M_alt         'P 2/c' 
_space_group_name_Hall            '-P 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, -y, -z' 
 'x, -y, z-1/2' 
  
_cell_length_a                    11.8634(5) 
_cell_length_b                    5.2240(2) 
_cell_length_c                    12.9213(6) 
_cell_angle_alpha                 90 
_cell_angle_beta                  95.765(5) 
_cell_angle_gamma                 90 
_cell_volume                      796.73(7) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     947 
_cell_measurement_theta_min       3.4330 
_cell_measurement_theta_max       27.4760 
  
_exptl_crystal_description        plates 
_exptl_crystal_colour             Colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.431 
_exptl_crystal_F_000              356 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.220 
_exptl_crystal_size_mid           0.115 
_exptl_crystal_size_min           0.049 
_exptl_absorpt_coefficient_mu     0.422 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.944 
_exptl_absorpt_correction_T_max   0.977 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'Enhance (Mo) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur 3 E' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  16.0382 
_diffrn_reflns_number             2869 
_diffrn_reflns_av_unetI/netI      0.0369 
_diffrn_reflns_av_R_equivalents   0.0180 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -6 
_diffrn_reflns_limit_k_max        6 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        11 
_diffrn_reflns_theta_min          3.169 
_diffrn_reflns_theta_max          28.292 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.818 
_diffrn_measured_fraction_theta_full  0.993 
_diffrn_reflns_Laue_measured_fraction_max    0.818 
_diffrn_reflns_Laue_measured_fraction_full   0.993 
_diffrn_reflns_point_group_measured_fraction_max   0.818 
_diffrn_reflns_point_group_measured_fraction_full  0.993 
_reflns_number_total              1613 
_reflns_number_gt                 1274 
_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        'CrysAlisPro, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)' 
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_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)+(0.0587P)²+0.3936P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          1613 
_refine_ls_number_parameters      105 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0615 
_refine_ls_R_factor_gt            0.0437 
_refine_ls_wR_factor_ref          0.1193 
_refine_ls_wR_factor_gt           0.1085 
_refine_ls_goodness_of_fit_ref    1.048 
_refine_ls_restrained_S_all       1.048 
_refine_ls_shift/su_max           0.004 
_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 
C1 C 0.36529(17) 0.3684(5) 0.42109(17) 0.0227(5) Uani 1 1 d . . . . . 
C2 C 0.37171(19) 0.2036(5) 0.33822(18) 0.0259(5) Uani 1 1 d . . . . . 
H2A H 0.434629 0.091442 0.337200 0.031 Uiso 1 1 calc R U . . . 
C3 C 0.28624(19) 0.2017(4) 0.25638(17) 0.0236(5) Uani 1 1 d . . . . . 
Cl3 Cl 0.29295(6) -0.00975(13) 0.15340(5) 0.0379(2) Uani 1 1 d . . . . . 
C4 C 0.19370(17) 0.3630(4) 0.25476(16) 0.0210(5) Uani 1 1 d . . . . . 
C5 C 0.18664(18) 0.5251(5) 0.34005(17) 0.0220(5) Uani 1 1 d . . . . . 
C6 C 0.27072(18) 0.5277(5) 0.42244(17) 0.0235(5) Uani 1 1 d . . . . . 
H6A H 0.264173 0.637875 0.480022 0.028 Uiso 1 1 calc R U . . . 
C7 C 0.46075(18) 0.3885(5) 0.50793(19) 0.0272(6) Uani 1 1 d . . . . . 
H7A H 0.504982 0.227504 0.511494 0.033 Uiso 1 1 calc R U . . . 
H7B H 0.428271 0.410130 0.575029 0.033 Uiso 1 1 calc R U . . . 
O8 O 0.11149(12) 0.3605(3) 0.17312(12) 0.0285(4) Uani 1 1 d D . . . . 
H8 H 0.0616(4) 0.4895(8) 0.1759(18) 0.060(10) Uiso 1 1 d D . . . . 
O9 O 0.08989(13) 0.6718(3) 0.33288(12) 0.0281(4) Uani 1 1 d . . . . . 
C10 C 0.0802(2) 0.8626(5) 0.41101(19) 0.0316(6) Uani 1 1 d . . . . . 
H10A H 0.011331 0.963410 0.393291 0.047 Uiso 1 1 calc R U . . . 
H10B H 0.146452 0.975649 0.414684 0.047 Uiso 1 1 calc R U . . . 
H10C H 0.076341 0.779435 0.478536 0.047 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 
C1 C2 1.382(3) . ? 
C1 C6 1.398(3) . ? 
C1 C7 1.516(3) . ? 
C2 C3 1.390(3) . ? 
C3 C4 1.383(3) . ? 
C3 Cl3 1.737(2) . ? 
C4 O8 1.363(2) . ? 
C4 C5 1.399(3) . ? 
C5 O9 1.375(3) . ? 
C5 C6 1.384(3) . ? 
C7 C7 1.518(5) 3_666 ? 
O9 C10 1.432(3) . ? 
  
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 
C2 C1 C6 119.2(2) . . ? 
C2 C1 C7 121.4(2) . . ? 
C6 C1 C7 119.4(2) . . ? 
C1 C2 C3 120.1(2) . . ? 
C4 C3 C2 121.7(2) . . ? 
C4 C3 Cl3 118.26(17) . . ? 
C2 C3 Cl3 120.08(18) . . ? 
O8 C4 C3 120.8(2) . . ? 
O8 C4 C5 121.38(19) . . ? 
C3 C4 C5 117.86(19) . . ? 
O9 C5 C6 125.3(2) . . ? 
O9 C5 C4 113.56(18) . . ? 
C6 C5 C4 121.1(2) . . ? 
C5 C6 C1 120.1(2) . . ? 
C1 C7 C7 112.1(2) . 3_666 ? 
C5 O9 C10 117.76(17) . . ? 
  
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 
O8 H8 O9  0.9000(1) 2.027(3) 2.884(2) 158.8(6) 2 yes 
  
_refine_diff_density_max    0.301 
_refine_diff_density_min   -0.344 
_refine_diff_density_rms    0.059 
  
  
  
#===END

