 
data_C15H13Cl3O2
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C15 H13 Cl3 O2'
_chemical_formula_sum
 'C15 H13 Cl3 O2' 
_chemical_formula_weight          331.60

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'
 'O'  'O'   0.0492   0.0322
 '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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'
 
_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+1/2, -z'
 
_cell_length_a                    8.0561(6)
_cell_length_b                    6.0406(4)
_cell_length_c                    14.5291(10)
_cell_angle_alpha                 90
_cell_angle_beta                  98.325(2)
_cell_angle_gamma                 90
_cell_volume                      699.59(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     9990
_cell_measurement_theta_min       3.07
_cell_measurement_theta_max       66.59
 
_exptl_crystal_description        block
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_method     none
_exptl_crystal_density_diffrn     1.574          
_exptl_crystal_F_000              340
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.600
_exptl_crystal_size_mid           0.300
_exptl_crystal_size_min           0.180
_exptl_absorpt_coefficient_mu     5.913
_shelx_estimated_absorpt_T_min    0.126
_shelx_estimated_absorpt_T_max    0.416
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.4327
_exptl_absorpt_correction_T_max   0.7528
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2013). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source                    'microfocus sealed tube'
_diffrn_source_type               'Incoatec I\uS'
_diffrn_radiation_monochromator   mirrors 
_diffrn_measurement_device_type   'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method        'φ and ω scans'  
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             10919
_diffrn_reflns_av_unetI/netI      0.0335
_diffrn_reflns_av_R_equivalents   0.0493
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.074
_diffrn_reflns_theta_max          66.586
_diffrn_reflns_theta_full         66.586
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              2470
_reflns_number_gt                 2460
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.808
_reflns_Friedel_fraction_max      0.996
_reflns_Friedel_fraction_full     0.996
 
_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        'APEX2 (Bruker, 2014)'
_computing_cell_refinement        'SAINT (Bruker, 2014)'
_computing_data_reduction         'SAINT (Bruker, 2014)'
_computing_structure_solution     'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_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)+(0.1507P)²+0.1466P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack    0.00(3)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          2470
_refine_ls_number_parameters      185
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0674
_refine_ls_R_factor_gt            0.0673
_refine_ls_wR_factor_ref          0.1729
_refine_ls_wR_factor_gt           0.1728
_refine_ls_goodness_of_fit_ref    1.109
_refine_ls_restrained_S_all       1.109
_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 0.69417(17) 0.2070(2) 0.17659(9) 0.0203(4) Uani 1 1 d . . . . .
Cl2 Cl 0.82851(16) 0.6502(2) 0.18898(9) 0.0199(4) Uani 1 1 d . . . . .
Cl3 Cl 0.55005(16) 0.5452(2) 0.05031(8) 0.0213(4) Uani 1 1 d . . . . .
O1 O 0.1994(5) 0.7270(9) 0.1217(3) 0.0283(12) Uani 1 1 d . . . . .
O2 O 0.4920(5) 0.7906(8) 0.2280(3) 0.0188(9) Uani 1 1 d D . . . .
H2O H 0.400(6) 0.799(17) 0.192(5) 0.028 Uiso 1 1 d D U . . .
C1 C 0.1185(8) 0.3642(14) 0.0704(5) 0.0273(15) Uani 1 1 d . . . . .
H1A H 0.0245 0.4407 0.0333 0.041 Uiso 1 1 calc R U . . .
H1B H 0.0752 0.2519 0.1095 0.041 Uiso 1 1 calc R U . . .
H1C H 0.1879 0.2925 0.0289 0.041 Uiso 1 1 calc R U . . .
C2 C 0.2218(7) 0.5272(12) 0.1306(4) 0.0221(14) Uani 1 1 d . . . . .
C3 C 0.3471(7) 0.4318(11) 0.2089(4) 0.0183(12) Uani 1 1 d . . . . .
H3A H 0.3748 0.2793 0.1912 0.022 Uiso 1 1 calc R U . . .
H3B H 0.2910 0.4205 0.2649 0.022 Uiso 1 1 calc R U . . .
C4 C 0.5147(7) 0.5597(12) 0.2360(4) 0.0166(12) Uani 1 1 d . . . . .
C5 C 0.5929(6) 0.5078(11) 0.3363(4) 0.0154(12) Uani 1 1 d . . . . .
C6 C 0.6907(6) 0.6664(10) 0.3860(4) 0.0152(12) Uani 1 1 d . . . . .
H6 H 0.7088 0.8044 0.3578 0.018 Uiso 1 1 calc R U . . .
C7 C 0.7649(7) 0.6256(12) 0.4792(4) 0.0155(12) Uani 1 1 d . . . . .
C8 C 0.8717(7) 0.7852(11) 0.5301(4) 0.0169(12) Uani 1 1 d . . . . .
H8 H 0.8941 0.9213 0.5014 0.020 Uiso 1 1 calc R U . . .
C9 C 0.9427(7) 0.7439(11) 0.6204(4) 0.0198(13) Uani 1 1 d . . . . .
H9 H 1.0155 0.8496 0.6537 0.024 Uiso 1 1 calc R U . . .
C10 C 0.9064(7) 0.5422(12) 0.6637(4) 0.0199(13) Uani 1 1 d . . . . .
H10 H 0.9532 0.5158 0.7265 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8059(7) 0.3858(12) 0.6165(4) 0.0196(13) Uani 1 1 d . . . . .
H11 H 0.7843 0.2512 0.6464 0.024 Uiso 1 1 calc R U . . .
C12 C 0.7327(7) 0.4238(11) 0.5222(4) 0.0165(13) Uani 1 1 d . . . . .
C13 C 0.6304(7) 0.2639(10) 0.4705(4) 0.0166(12) Uani 1 1 d . . . . .
H13 H 0.6073 0.1280 0.4990 0.020 Uiso 1 1 calc R U . . .
C14 C 0.5641(7) 0.3031(11) 0.3795(4) 0.0172(12) Uani 1 1 d . . . . .
H14 H 0.4984 0.1922 0.3451 0.021 Uiso 1 1 calc R U . . .
C15 C 0.6418(7) 0.4923(11) 0.1670(4) 0.0171(12) 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 C15 1.775(6) . ?
Cl2 C15 1.771(6) . ?
Cl3 C15 1.777(6) . ?
O1 C2 1.225(9) . ?
O2 C4 1.409(9) . ?
O2 H2O 0.84(3) . ?
C1 C2 1.489(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.521(9) . ?
C3 C4 1.556(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.533(7) . ?
C4 C15 1.586(8) . ?
C5 C6 1.377(8) . ?
C5 C14 1.421(9) . ?
C6 C7 1.419(7) . ?
C6 H6 0.9500 . ?
C7 C12 1.411(9) . ?
C7 C8 1.426(9) . ?
C8 C9 1.377(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.420(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.363(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.430(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.413(9) . ?
C13 C14 1.373(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
 
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
C4 O2 H2O 102(7) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 121.9(6) . . ?
O1 C2 C3 121.6(6) . . ?
C1 C2 C3 116.3(6) . . ?
C2 C3 C4 117.3(5) . . ?
C2 C3 H3A 108.0 . . ?
C4 C3 H3A 108.0 . . ?
C2 C3 H3B 108.0 . . ?
C4 C3 H3B 108.0 . . ?
H3A C3 H3B 107.2 . . ?
O2 C4 C5 108.2(5) . . ?
O2 C4 C3 111.9(5) . . ?
C5 C4 C3 111.2(5) . . ?
O2 C4 C15 106.8(5) . . ?
C5 C4 C15 109.5(4) . . ?
C3 C4 C15 109.1(5) . . ?
C6 C5 C14 119.4(5) . . ?
C6 C5 C4 118.8(5) . . ?
C14 C5 C4 121.8(5) . . ?
C5 C6 C7 120.6(6) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C12 C7 C6 119.6(6) . . ?
C12 C7 C8 119.4(5) . . ?
C6 C7 C8 121.1(6) . . ?
C9 C8 C7 120.5(6) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.6(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 121.2(5) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.2(6) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C13 119.0(5) . . ?
C7 C12 C11 119.1(6) . . ?
C13 C12 C11 121.8(6) . . ?
C14 C13 C12 120.6(6) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C5 120.6(5) . . ?
C13 C14 H14 119.7 . . ?
C5 C14 H14 119.7 . . ?
C4 C15 Cl2 110.9(4) . . ?
C4 C15 Cl1 111.6(4) . . ?
Cl2 C15 Cl1 108.8(3) . . ?
C4 C15 Cl3 109.9(4) . . ?
Cl2 C15 Cl3 107.5(3) . . ?
Cl1 C15 Cl3 108.1(3) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O1 C2 C3 C4 -38.2(9) . . . . ?
C1 C2 C3 C4 146.6(5) . . . . ?
C2 C3 C4 O2 35.3(7) . . . . ?
C2 C3 C4 C5 156.4(5) . . . . ?
C2 C3 C4 C15 -82.7(7) . . . . ?
O2 C4 C5 C6 -27.7(7) . . . . ?
C3 C4 C5 C6 -150.9(5) . . . . ?
C15 C4 C5 C6 88.4(6) . . . . ?
O2 C4 C5 C14 151.0(5) . . . . ?
C3 C4 C5 C14 27.7(8) . . . . ?
C15 C4 C5 C14 -92.9(6) . . . . ?
C14 C5 C6 C7 1.0(8) . . . . ?
C4 C5 C6 C7 179.7(5) . . . . ?
C5 C6 C7 C12 -2.4(8) . . . . ?
C5 C6 C7 C8 177.5(5) . . . . ?
C12 C7 C8 C9 -0.1(8) . . . . ?
C6 C7 C8 C9 179.9(5) . . . . ?
C7 C8 C9 C10 -1.2(8) . . . . ?
C8 C9 C10 C11 1.7(9) . . . . ?
C9 C10 C11 C12 -0.8(9) . . . . ?
C6 C7 C12 C13 1.7(8) . . . . ?
C8 C7 C12 C13 -178.3(6) . . . . ?
C6 C7 C12 C11 -179.0(5) . . . . ?
C8 C7 C12 C11 1.0(8) . . . . ?
C10 C11 C12 C7 -0.6(8) . . . . ?
C10 C11 C12 C13 178.8(5) . . . . ?
C7 C12 C13 C14 0.5(8) . . . . ?
C11 C12 C13 C14 -178.8(5) . . . . ?
C12 C13 C14 C5 -1.9(8) . . . . ?
C6 C5 C14 C13 1.1(8) . . . . ?
C4 C5 C14 C13 -177.5(5) . . . . ?
O2 C4 C15 Cl2 54.1(5) . . . . ?
C5 C4 C15 Cl2 -62.8(6) . . . . ?
C3 C4 C15 Cl2 175.2(4) . . . . ?
O2 C4 C15 Cl1 175.5(4) . . . . ?
C5 C4 C15 Cl1 58.6(6) . . . . ?
C3 C4 C15 Cl1 -63.3(5) . . . . ?
O2 C4 C15 Cl3 -64.6(5) . . . . ?
C5 C4 C15 Cl3 178.5(4) . . . . ?
C3 C4 C15 Cl3 56.6(6) . . . . ?
 
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 
O2 H2O O1  0.84(3) 1.84(4) 2.652(6) 163(10) .
 
_refine_diff_density_max    0.375
_refine_diff_density_min   -0.350
_refine_diff_density_rms    0.072



