data_2005src0668
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C20 H18 Cl N O2'
_chemical_formula_sum
 'C20 H18 Cl N O2'
_chemical_formula_weight          339.80
 
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'
 'N'  'N'   0.0061   0.0033
 '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'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Pbca
_symmetry_space_group_name_hall   '-P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    14.0434(9)
_cell_length_b                    13.6783(8)
_cell_length_c                    16.8919(10)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3244.8(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4079
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.391
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1424
_exptl_absorpt_coefficient_mu     0.247
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9294
_exptl_absorpt_correction_T_max   0.9522
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             20464
_diffrn_reflns_av_R_equivalents   0.0340
_diffrn_reflns_av_sigmaI/netI     0.0283
_diffrn_reflns_limit_h_min        -18
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          3.26
_diffrn_reflns_theta_max          27.49
_reflns_number_total              3719
_reflns_number_gt                 3073
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT'
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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)+(0.0489P)²+1.5415P] 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      SHELXL
_refine_ls_extinction_coef        0.0067(9)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3719
_refine_ls_number_parameters      218
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0476
_refine_ls_R_factor_gt            0.0353
_refine_ls_wR_factor_ref          0.0966
_refine_ls_wR_factor_gt           0.0894
_refine_ls_goodness_of_fit_ref    1.015
_refine_ls_restrained_S_all       1.015
_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
C1 C 0.04967(9) 0.76276(10) 0.43663(8) 0.0175(3) Uani 1 1 d . . .
C2 C 0.09518(9) 0.81839(11) 0.48818(9) 0.0214(3) Uani 1 1 d . . .
H2A H 0.0791 0.8856 0.4931 0.026 Uiso 1 1 calc R . .
H2B H 0.1440 0.7912 0.5203 0.026 Uiso 1 1 calc R . .
C3 C -0.02778(9) 0.79998(9) 0.38410(8) 0.0160(3) Uani 1 1 d . . .
N1 N -0.09007(8) 0.86658(8) 0.41964(6) 0.0139(2) Uani 1 1 d . . .
C5 C -0.11908(9) 0.86198(9) 0.49981(7) 0.0148(3) Uani 1 1 d . . .
C6 C -0.13320(8) 0.76389(10) 0.53620(7) 0.0143(3) Uani 1 1 d . . .
C7 C -0.13627(10) 0.75869(10) 0.61864(8) 0.0194(3) Uani 1 1 d . . .
H7 H -0.1228 0.8152 0.6494 0.023 Uiso 1 1 calc R . .
C8 C -0.15882(10) 0.67159(11) 0.65587(8) 0.0232(3) Uani 1 1 d . . .
H8 H -0.1596 0.6681 0.7120 0.028 Uiso 1 1 calc R . .
C9 C -0.18025(10) 0.58950(10) 0.61125(9) 0.0220(3) Uani 1 1 d . . .
H9 H -0.1974 0.5302 0.6369 0.026 Uiso 1 1 calc R . .
C10 C -0.17672(10) 0.59356(10) 0.52938(8) 0.0203(3) Uani 1 1 d . . .
H10 H -0.1909 0.5369 0.4990 0.024 Uiso 1 1 calc R . .
C11 C -0.15259(9) 0.68011(10) 0.49172(8) 0.0171(3) Uani 1 1 d . . .
H11 H -0.1492 0.6825 0.4356 0.021 Uiso 1 1 calc R . .
C12 C -0.12615(9) 0.94638(9) 0.37212(7) 0.0145(3) Uani 1 1 d . . .
C13 C -0.06373(9) 1.01948(10) 0.34978(8) 0.0174(3) Uani 1 1 d . . .
H13 H 0.0013 1.0166 0.3651 0.021 Uiso 1 1 calc R . .
C14 C -0.09718(10) 1.09716(10) 0.30474(8) 0.0192(3) Uani 1 1 d . . .
H14 H -0.0549 1.1472 0.2878 0.023 Uiso 1 1 calc R . .
C15 C -0.19275(10) 1.10087(10) 0.28477(8) 0.0191(3) Uani 1 1 d . . .
H15 H -0.2158 1.1548 0.2550 0.023 Uiso 1 1 calc R . .
C16 C -0.25611(9) 1.02737(10) 0.30735(7) 0.0161(3) Uani 1 1 d . . .
C17 C -0.35951(9) 1.03380(11) 0.28245(9) 0.0216(3) Uani 1 1 d . . .
H17A H -0.3645 1.0180 0.2254 0.026 Uiso 1 1 calc R . .
H17B H -0.3820 1.1018 0.2898 0.026 Uiso 1 1 calc R . .
C18 C -0.42367(10) 0.96536(11) 0.32875(10) 0.0254(3) Uani 1 1 d . . .
H18A H -0.4875 0.9634 0.3039 0.031 Uiso 1 1 calc R . .
H18B H -0.4310 0.9898 0.3836 0.031 Uiso 1 1 calc R . .
C19 C -0.38138(10) 0.86327(11) 0.33027(10) 0.0257(3) Uani 1 1 d . . .
H19A H -0.3715 0.8400 0.2754 0.031 Uiso 1 1 calc R . .
H19B H -0.4261 0.8179 0.3568 0.031 Uiso 1 1 calc R . .
C20 C -0.28668(9) 0.86366(10) 0.37433(8) 0.0187(3) Uani 1 1 d . . .
H20A H -0.2993 0.8675 0.4319 0.022 Uiso 1 1 calc R . .
H20B H -0.2533 0.8012 0.3639 0.022 Uiso 1 1 calc R . .
C21 C -0.22241(9) 0.94747(9) 0.35083(7) 0.0145(3) Uani 1 1 d . . .
O1 O -0.03165(7) 0.78060(7) 0.31428(6) 0.0239(2) Uani 1 1 d . . .
O2 O -0.13965(7) 0.93697(7) 0.53440(6) 0.0201(2) Uani 1 1 d . . .
Cl1 Cl 0.08463(3) 0.64422(3) 0.41680(2) 0.02989(13) 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
C1 C2 1.321(2) . ?
C1 C3 1.4932(18) . ?
C1 Cl1 1.7270(14) . ?
C2 H2A 0.9500 . ?
C2 H2B 0.9500 . ?
C3 O1 1.2100(17) . ?
C3 N1 1.3984(16) . ?
N1 C5 1.4155(16) . ?
N1 C12 1.4465(16) . ?
C5 O2 1.2153(16) . ?
C5 C6 1.4890(18) . ?
C6 C7 1.3950(19) . ?
C6 C11 1.3970(19) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3861(19) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.3823(19) . ?
C12 C21 1.3988(18) . ?
C13 C14 1.3886(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3956(19) . ?
C15 H15 0.9500 . ?
C16 C21 1.3992(18) . ?
C16 C17 1.5144(18) . ?
C17 C18 1.517(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.518(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.5239(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.5121(18) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
 
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 C3 123.21(12) . . ?
C2 C1 Cl1 122.07(11) . . ?
C3 C1 Cl1 114.33(10) . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 H2B 120.0 . . ?
H2A C2 H2B 120.0 . . ?
O1 C3 N1 122.22(12) . . ?
O1 C3 C1 122.49(12) . . ?
N1 C3 C1 115.00(11) . . ?
C3 N1 C5 124.18(11) . . ?
C3 N1 C12 118.19(10) . . ?
C5 N1 C12 117.62(10) . . ?
O2 C5 N1 119.39(12) . . ?
O2 C5 C6 122.03(12) . . ?
N1 C5 C6 118.25(11) . . ?
C7 C6 C11 119.28(12) . . ?
C7 C6 C5 117.52(12) . . ?
C11 C6 C5 122.89(11) . . ?
C8 C7 C6 120.30(13) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.01(13) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.20(13) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 120.09(13) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 120.09(12) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
C13 C12 C21 122.33(12) . . ?
C13 C12 N1 118.37(11) . . ?
C21 C12 N1 119.29(11) . . ?
C12 C13 C14 119.25(12) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 119.29(12) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 121.67(12) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C21 119.37(12) . . ?
C15 C16 C17 119.58(12) . . ?
C21 C16 C17 121.03(12) . . ?
C16 C17 C18 113.00(11) . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C19 110.13(12) . . ?
C17 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 C20 110.27(12) . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C21 C20 C19 113.29(11) . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C12 C21 C16 118.05(12) . . ?
C12 C21 C20 120.08(11) . . ?
C16 C21 C20 121.87(11) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.302
_refine_diff_density_min   -0.325
_refine_diff_density_rms    0.048
