 
data_sk
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H14 Cl N O2'
_chemical_formula_weight          239.69
 
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'
 'N'  'N'   0.0311   0.0180
 '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'
 
_symmetry_cell_setting            ?
_symmetry_space_group_name_H-M    ?
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    6.8720(2)
_cell_length_b                    22.4177(4)
_cell_length_c                    7.7044(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.798(2)
_cell_angle_gamma                 90.00
_cell_volume                      1186.78(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     7834
_cell_measurement_theta_min       4
_cell_measurement_theta_max       70
 
_exptl_crystal_description        prism
_exptl_crystal_colour             brown
_exptl_crystal_size_max           .17
_exptl_crystal_size_mid           .12
_exptl_crystal_size_min           .06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.342
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              504
_exptl_absorpt_coefficient_mu     2.733
 
_exptl_special_details
;
 ?
;
_diffrn_detector                   'Pilatus100K'
_diffrn_detector_type              'STOE'
_diffrn_detector_area_resol_mean   5.81
_diffrn_source           'Cu GeniX 3D'
_diffrn_source_voltage             50
_diffrn_source_current             0.600
_diffrn_source_power               0.030
_diffrn_radiation_type             'Cu K\a'
_diffrn_radiation_wavelength       1.54086
_diffrn_radiation_monochromator    'none'
_diffrn_radiation_polarisn_norm    0
_diffrn_radiation_collimation      'focusing mirrors'
_diffrn_ambient_temperature        295
_diffrn_measurement_method         'rotation method'  
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             3787
_diffrn_reflns_av_R_equivalents   0.0827
_diffrn_reflns_av_sigmaI/netI     0.0777
_diffrn_reflns_limit_h_min        -3
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -27
_diffrn_reflns_limit_k_max        25
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        8
_diffrn_reflns_theta_min          3.94
_diffrn_reflns_theta_max          70.03
_reflns_number_total              2100
_reflns_number_gt                 1343
_reflns_threshold_expression      >2sigma(I)
_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0701P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0089(10)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2100
_refine_ls_number_parameters      202
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0735
_refine_ls_R_factor_gt            0.0507
_refine_ls_wR_factor_ref          0.1283
_refine_ls_wR_factor_gt           0.1203
_refine_ls_goodness_of_fit_ref    0.875
_refine_ls_restrained_S_all       0.875
_refine_ls_shift/su_max           0.186
_refine_ls_shift/su_mean          0.019
 
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_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl1 Cl 1.41111(12) 0.82589(3) 1.48582(11) 0.0686(3) Uani 1 1 d . . .
O1 O 0.4973(3) 0.88790(10) 1.0248(3) 0.0606(6) Uani 1 1 d . . .
N1 N 1.0273(3) 0.86091(10) 1.2712(3) 0.0538(6) Uani 1 1 d . . .
C2 C 0.8989(5) 0.80953(15) 1.2528(6) 0.0741(10) Uani 1 1 d . . .
C3 C 0.7513(5) 0.81711(14) 1.1099(5) 0.0642(8) Uani 1 1 d . . .
C4 C 0.6656(4) 0.87845(12) 1.1021(3) 0.0478(6) Uani 1 1 d . . .
C5 C 0.7376(4) 0.99059(12) 1.1488(4) 0.0469(6) Uani 1 1 d . . .
C6 C 0.9771(4) 1.07534(12) 1.2421(4) 0.0536(7) Uani 1 1 d . . .
C7 C 1.1567(5) 1.08801(14) 1.3171(4) 0.0562(7) Uani 1 1 d . . .
C8 C 1.2815(4) 1.04319(13) 1.3706(3) 0.0533(7) Uani 1 1 d . . .
C9 C 1.2326(4) 0.98407(14) 1.3506(3) 0.0504(7) Uani 1 1 d . . .
C10 C 1.0513(4) 0.97089(11) 1.2749(3) 0.0422(6) Uani 1 1 d . . .
C11 C 0.9230(4) 1.01607(11) 1.2220(3) 0.0430(6) Uani 1 1 d . . .
C12 C 0.9586(4) 0.91395(11) 1.2406(3) 0.0440(6) Uani 1 1 d . . .
C13 C 0.7713(4) 0.92463(12) 1.1643(3) 0.0446(6) Uani 1 1 d . . .
O9 O 0.3166(4) 0.80207(11) 0.8737(3) 0.0779(7) Uani 1 1 d . . .
H1N H 1.132(5) 0.8531(16) 1.332(4) 0.079(11) Uiso 1 1 d . . .
H2 H 0.986(7) 0.778(2) 1.220(5) 0.119(14) Uiso 1 1 d . . .
H21 H 0.829(8) 0.806(2) 1.397(8) 0.17(2) Uiso 1 1 d . . .
H3 H 0.659(5) 0.7858(17) 1.111(4) 0.082(10) Uiso 1 1 d . . .
H31 H 0.796(5) 0.8115(13) 0.995(4) 0.068(9) Uiso 1 1 d . . .
H5 H 0.715(4) 1.0053(12) 1.023(4) 0.056(8) Uiso 1 1 d . . .
H6 H 0.889(4) 1.1026(13) 1.201(3) 0.054(8) Uiso 1 1 d . . .
H7 H 1.183(4) 1.1273(14) 1.333(3) 0.053(8) Uiso 1 1 d . . .
H8 H 1.406(4) 1.0526(13) 1.420(4) 0.060(8) Uiso 1 1 d . . .
H9 H 1.316(4) 0.9521(14) 1.396(4) 0.065(9) Uiso 1 1 d . . .
H1O H 0.435(6) 0.854(2) 0.969(5) 0.106(13) Uiso 1 1 d . . .
H51 H 0.630(4) 1.0029(13) 1.224(4) 0.068(9) Uiso 1 1 d . . .
H91 H 0.341(6) 0.7582(19) 0.901(5) 0.108(13) Uiso 1 1 d . . .
H92 H 0.354(7) 0.804(3) 0.733(8) 0.17(2) Uiso 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
O1 C4 1.311(3) . ?
N1 C12 1.300(3) . ?
N1 C2 1.457(4) . ?
C2 C3 1.496(5) . ?
C3 C4 1.497(4) . ?
C4 C13 1.349(4) . ?
C5 C11 1.499(4) . ?
C5 C13 1.501(4) . ?
C6 C7 1.385(4) . ?
C6 C11 1.388(4) . ?
C7 C8 1.380(4) . ?
C8 C9 1.376(4) . ?
C9 C10 1.400(4) . ?
C10 C11 1.399(4) . ?
C10 C12 1.449(4) . ?
C12 C13 1.427(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
C12 N1 C2 119.2(3) . . ?
N1 C2 C3 112.7(3) . . ?
C2 C3 C4 113.3(3) . . ?
O1 C4 C13 120.3(2) . . ?
O1 C4 C3 120.7(2) . . ?
C13 C4 C3 118.7(3) . . ?
C11 C5 C13 102.5(2) . . ?
C7 C6 C11 118.6(3) . . ?
C8 C7 C6 121.4(3) . . ?
C9 C8 C7 121.2(3) . . ?
C8 C9 C10 117.7(3) . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 C12 108.1(2) . . ?
C9 C10 C12 130.4(2) . . ?
C6 C11 C10 119.6(3) . . ?
C6 C11 C5 129.2(2) . . ?
C10 C11 C5 111.2(2) . . ?
N1 C12 C13 123.4(2) . . ?
N1 C12 C10 128.0(3) . . ?
C13 C12 C10 108.6(2) . . ?
C4 C13 C12 119.7(2) . . ?
C4 C13 C5 130.2(2) . . ?
C12 C13 C5 109.6(2) . . ?
 
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
C12 N1 C2 C3 34.2(5) . . . . ?
N1 C2 C3 C4 -41.2(5) . . . . ?
C2 C3 C4 O1 -158.7(3) . . . . ?
C2 C3 C4 C13 26.4(5) . . . . ?
C11 C6 C7 C8 0.3(4) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C8 C9 C10 C12 -178.6(2) . . . . ?
C7 C6 C11 C10 -1.0(4) . . . . ?
C7 C6 C11 C5 178.7(3) . . . . ?
C9 C10 C11 C6 1.0(4) . . . . ?
C12 C10 C11 C6 179.6(2) . . . . ?
C9 C10 C11 C5 -178.8(2) . . . . ?
C12 C10 C11 C5 -0.2(3) . . . . ?
C13 C5 C11 C6 -179.8(3) . . . . ?
C13 C5 C11 C10 -0.1(3) . . . . ?
C2 N1 C12 C13 -9.8(4) . . . . ?
C2 N1 C12 C10 170.2(3) . . . . ?
C11 C10 C12 N1 -179.6(3) . . . . ?
C9 C10 C12 N1 -1.2(4) . . . . ?
C11 C10 C12 C13 0.4(3) . . . . ?
C9 C10 C12 C13 178.8(2) . . . . ?
O1 C4 C13 C12 -177.0(2) . . . . ?
C3 C4 C13 C12 -2.0(4) . . . . ?
O1 C4 C13 C5 -5.7(4) . . . . ?
C3 C4 C13 C5 169.2(3) . . . . ?
N1 C12 C13 C4 -7.6(4) . . . . ?
C10 C12 C13 C4 172.4(2) . . . . ?
N1 C12 C13 C5 179.5(2) . . . . ?
C10 C12 C13 C5 -0.5(3) . . . . ?
C11 C5 C13 C4 -171.5(3) . . . . ?
C11 C5 C13 C12 0.4(3) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.928
_diffrn_reflns_theta_full              70.03
_diffrn_measured_fraction_theta_full   0.928
_refine_diff_density_max    0.273
_refine_diff_density_min   -0.299
_refine_diff_density_rms    0.069
