 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H17 Cl3'
_chemical_formula_weight          351.68
 
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'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    P2(1)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
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                    12.242(2)
_cell_length_b                    9.8900(10)
_cell_length_c                    14.073(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.89(2)
_cell_angle_gamma                 90.00
_cell_volume                      1687.7(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        unknown
_exptl_crystal_colour             unknown
_exptl_crystal_size_max           0.5
_exptl_crystal_size_mid           0.3
_exptl_crystal_size_min           0.1
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.384
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              728
_exptl_absorpt_coefficient_mu     0.536
_exptl_absorpt_correction_type    none

 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'
_diffrn_reflns_number             3985
_diffrn_reflns_av_R_equivalents   0.0813
_diffrn_reflns_av_sigmaI/netI     0.2418
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -3
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.52
_diffrn_reflns_theta_max          25.16
_reflns_number_total              2102
_reflns_number_gt                 973
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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 > 2σ(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)+(0.0234P)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     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2102
_refine_ls_number_parameters      200
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1011
_refine_ls_R_factor_gt            0.0425
_refine_ls_wR_factor_ref          0.1046
_refine_ls_wR_factor_gt           0.0947
_refine_ls_goodness_of_fit_ref    0.633
_refine_ls_restrained_S_all       0.633
_refine_ls_shift/su_max           0.005
_refine_ls_shift/su_mean          0.001
 
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 -0.00177(12) 0.22367(16) 0.07919(10) 0.0262(4) Uani 1 1 d . . .
Cl2 Cl -0.25679(14) 0.19345(17) 0.13349(10) 0.0344(5) Uani 1 1 d . . .
Cl3 Cl -0.31427(15) 0.55813(18) -0.13251(11) 0.0430(6) Uani 1 1 d . . .
C14 C -0.0102(5) 0.2804(6) -0.1421(3) 0.0181(15) Uani 1 1 d . . .
C7 C -0.1185(5) 0.2655(6) -0.1061(3) 0.0184(15) Uani 1 1 d . . .
H7 H -0.1785 0.3221 -0.1415 0.022 Uiso 1 1 calc R . .
C15 C 0.0171(5) 0.4025(6) -0.1794(3) 0.0206(15) Uani 1 1 d . . .
H15 H -0.0333 0.4755 -0.1797 0.025 Uiso 1 1 calc R . .
C4 C -0.2126(5) 0.3048(6) 0.0494(4) 0.0200(15) Uani 1 1 d . . .
C3 C -0.2181(5) 0.5319(6) -0.0224(4) 0.0256(17) Uani 1 1 d . . .
H3A H -0.1453 0.5035 -0.0385 0.031 Uiso 1 1 calc R . .
H3B H -0.2083 0.6173 0.0145 0.031 Uiso 1 1 calc R . .
C18 C 0.1622(5) 0.1949(7) -0.1804(4) 0.0267(16) Uani 1 1 d . . .
H18 H 0.2121 0.1215 -0.1816 0.032 Uiso 1 1 calc R . .
C19 C 0.0676(5) 0.1756(6) -0.1425(4) 0.0238(15) Uani 1 1 d . . .
H19 H 0.0536 0.0903 -0.1157 0.029 Uiso 1 1 calc R . .
C8 C -0.2754(5) 0.0879(6) -0.0963(4) 0.0245(16) Uani 1 1 d . . .
C2 C -0.2639(5) 0.4240(6) 0.0369(4) 0.0199(15) Uani 1 1 d . . .
C16 C 0.1144(5) 0.4236(6) -0.2165(3) 0.0222(15) Uani 1 1 d . . .
H16 H 0.1305 0.5097 -0.2410 0.027 Uiso 1 1 calc R . .
C6 C -0.1586(5) 0.1312(6) -0.0717(4) 0.0215(15) Uani 1 1 d . . .
H6 H -0.1034 0.0562 -0.0682 0.026 Uiso 1 1 calc R . .
C17 C 0.1881(5) 0.3182(7) -0.2174(4) 0.0265(17) Uani 1 1 d . . .
H17 H 0.2553 0.3303 -0.2430 0.032 Uiso 1 1 calc R . .
C5 C -0.1293(4) 0.2459(6) 0.0020(4) 0.0185(15) Uani 1 1 d . . .
C1 C -0.3633(5) 0.4631(7) 0.0831(4) 0.0341(18) Uani 1 1 d . . .
H1A H -0.3478 0.4483 0.1525 0.051 Uiso 1 1 calc R . .
H1B H -0.4265 0.4076 0.0564 0.051 Uiso 1 1 calc R . .
H1C H -0.3804 0.5588 0.0704 0.051 Uiso 1 1 calc R . .
C13 C -0.3582(5) 0.1733(7) -0.1396(4) 0.0350(19) Uani 1 1 d . . .
H13 H -0.3408 0.2637 -0.1545 0.042 Uiso 1 1 calc R . .
C11 C -0.4928(7) 0.0005(10) -0.1390(5) 0.061(3) Uani 1 1 d . . .
H11 H -0.5674 -0.0281 -0.1522 0.073 Uiso 1 1 calc R . .
C10 C -0.4116(6) -0.0876(8) -0.0974(5) 0.054(2) Uani 1 1 d . . .
H10 H -0.4294 -0.1785 -0.0840 0.065 Uiso 1 1 calc R . .
C9 C -0.3041(6) -0.0413(7) -0.0756(4) 0.0395(19) Uani 1 1 d . . .
H9 H -0.2490 -0.1009 -0.0456 0.047 Uiso 1 1 calc R . .
C12 C -0.4636(6) 0.1280(9) -0.1606(4) 0.051(2) Uani 1 1 d . . .
H12 H -0.5185 0.1874 -0.1913 0.061 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C5 1.789(6) . ?
Cl2 C4 1.755(6) . ?
Cl3 C3 1.832(5) . ?
C14 C15 1.376(7) . ?
C14 C19 1.408(8) . ?
C14 C7 1.491(7) . ?
C7 C6 1.518(8) . ?
C7 C5 1.557(7) . ?
C7 H7 1.0000 . ?
C15 C16 1.379(8) . ?
C15 H15 0.9500 . ?
C4 C2 1.337(8) . ?
C4 C5 1.419(8) . ?
C3 C2 1.509(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C18 C19 1.354(8) . ?
C18 C17 1.380(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C8 C9 1.367(8) . ?
C8 C13 1.393(8) . ?
C8 C6 1.487(7) . ?
C2 C1 1.506(8) . ?
C16 C17 1.379(8) . ?
C16 H16 0.9500 . ?
C6 C5 1.545(7) . ?
C6 H6 1.0000 . ?
C17 H17 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C13 C12 1.360(8) . ?
C13 H13 0.9500 . ?
C11 C12 1.356(10) . ?
C11 C10 1.390(10) . ?
C11 H11 0.9500 . ?
C10 C9 1.387(8) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C12 H12 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
C15 C14 C19 116.4(6) . . ?
C15 C14 C7 119.4(6) . . ?
C19 C14 C7 124.2(6) . . ?
C14 C7 C6 122.5(5) . . ?
C14 C7 C5 122.9(4) . . ?
C6 C7 C5 60.3(3) . . ?
C14 C7 H7 113.7 . . ?
C6 C7 H7 113.7 . . ?
C5 C7 H7 113.7 . . ?
C16 C15 C14 123.0(6) . . ?
C16 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C2 C4 C5 131.0(6) . . ?
C2 C4 Cl2 117.4(5) . . ?
C5 C4 Cl2 111.6(4) . . ?
C2 C3 Cl3 108.9(4) . . ?
C2 C3 H3A 109.9 . . ?
Cl3 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
Cl3 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C19 C18 C17 121.7(6) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C14 120.9(6) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C9 C8 C13 117.8(6) . . ?
C9 C8 C6 119.1(6) . . ?
C13 C8 C6 123.1(6) . . ?
C4 C2 C3 119.5(6) . . ?
C4 C2 C1 124.2(6) . . ?
C3 C2 C1 116.2(6) . . ?
C15 C16 C17 119.2(6) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C8 C6 C7 121.3(5) . . ?
C8 C6 C5 119.6(5) . . ?
C7 C6 C5 61.1(3) . . ?
C8 C6 H6 114.8 . . ?
C7 C6 H6 114.8 . . ?
C5 C6 H6 114.8 . . ?
C18 C17 C16 118.7(6) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C4 C5 C6 120.1(5) . . ?
C4 C5 C7 124.9(5) . . ?
C6 C5 C7 58.6(3) . . ?
C4 C5 Cl1 112.9(4) . . ?
C6 C5 Cl1 114.8(4) . . ?
C7 C5 Cl1 115.1(4) . . ?
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 . . ?
C12 C13 C8 120.5(7) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C12 C11 C10 118.9(7) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C9 C10 C11 119.2(7) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C8 C9 C10 121.7(7) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C12 C13 121.9(8) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
 
_diffrn_measured_fraction_theta_max    0.693
_diffrn_reflns_theta_full              25.16
_diffrn_measured_fraction_theta_full   0.693
_refine_diff_density_max    0.235
_refine_diff_density_min   -0.310
_refine_diff_density_rms    0.064
