data_2005src0807
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C20 H16 Cl2 N O2, Cl'
_chemical_formula_sum
 'C20 H16 Cl3 N O2'
_chemical_formula_weight          408.69
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   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    Pna2(1)
_symmetry_space_group_name_hall   'P 2c -2n' 
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 'x+1/2, -y+1/2, z'
 '-x+1/2, y+1/2, z+1/2'
 
_cell_length_a                    11.681(19)
_cell_length_b                    19.120(15)
_cell_length_c                    8.296(13)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1853(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2154
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.1
 
_exptl_crystal_description        shard
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.465
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              840
_exptl_absorpt_coefficient_mu     0.509
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8876
_exptl_absorpt_correction_T_max   0.9701
_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             12469
_diffrn_reflns_av_R_equivalents   0.0676
_diffrn_reflns_av_sigmaI/netI     0.0818
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -24
_diffrn_reflns_limit_k_max        22
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          3.19
_diffrn_reflns_theta_max          27.16
_reflns_number_total              3685
_reflns_number_gt                 2757
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_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)+(0.0423P)²+0.4806P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.08(8)
_refine_ls_number_reflns          3685
_refine_ls_number_parameters      265
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0865
_refine_ls_R_factor_gt            0.0540
_refine_ls_wR_factor_ref          0.1105
_refine_ls_wR_factor_gt           0.1000
_refine_ls_goodness_of_fit_ref    1.041
_refine_ls_restrained_S_all       1.041
_refine_ls_shift/su_max           0.007
_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 0.4123(5) 0.5715(5) 0.0953(8) 0.042(3) Uani 0.640(18) 1 d P A 1
C2 C 0.461(2) 0.6329(9) 0.1169(11) 0.036(5) Uani 0.68(6) 1 d P A 1
Cl1 Cl 0.4779(11) 0.4976(2) 0.0326(4) 0.0518(16) Uani 0.58(3) 1 d P A 1
C1' C 0.5094(12) 0.5969(8) 0.0853(14) 0.037(5) Uani 0.360(18) 1 d P A 2
C2' C 0.409(4) 0.6160(14) 0.142(4) 0.035(7) Uani 0.32(6) 1 d P A 2
Cl1' Cl 0.5348(18) 0.5110(5) 0.0292(6) 0.058(3) Uani 0.42(3) 1 d P A 2
C3 C 0.3914(3) 0.69655(17) 0.1647(5) 0.0374(8) Uani 1 1 d . . .
C4 C 0.5084(3) 0.70773(18) 0.4044(4) 0.0336(8) Uani 1 1 d . . .
C5 C 0.5893(3) 0.75167(17) 0.4974(5) 0.0306(8) Uani 1 1 d . A .
C6 C 0.6142(3) 0.72929(18) 0.6541(5) 0.0347(8) Uani 1 1 d . . .
H6 H 0.5755 0.6900 0.6981 0.042 Uiso 1 1 calc R A .
C7 C 0.6952(3) 0.7643(2) 0.7448(5) 0.0415(10) Uani 1 1 d . A .
H7 H 0.7113 0.7500 0.8521 0.050 Uiso 1 1 calc R . .
C8 C 0.7524(3) 0.82044(19) 0.6778(5) 0.0421(10) Uani 1 1 d . . .
H8 H 0.8085 0.8445 0.7395 0.051 Uiso 1 1 calc R A .
C9 C 0.7291(3) 0.84226(18) 0.5220(5) 0.0403(9) Uani 1 1 d . A .
H9 H 0.7699 0.8807 0.4775 0.048 Uiso 1 1 calc R . .
C10 C 0.6471(3) 0.80855(17) 0.4309(5) 0.0355(9) Uani 1 1 d . . .
H10 H 0.6303 0.8239 0.3246 0.043 Uiso 1 1 calc R A .
C11 C 0.4059(3) 0.81065(16) 0.2865(5) 0.0281(7) Uani 1 1 d . . .
C12 C 0.3523(3) 0.82972(17) 0.4270(4) 0.0305(8) Uani 1 1 d . A .
H12 H 0.3451 0.7973 0.5132 0.037 Uiso 1 1 calc R . .
C13 C 0.3086(3) 0.89709(17) 0.4419(5) 0.0345(8) Uani 1 1 d . . .
H13 H 0.2719 0.9114 0.5386 0.041 Uiso 1 1 calc R A .
C14 C 0.3192(3) 0.94263(18) 0.3144(5) 0.0375(9) Uani 1 1 d . A .
H14 H 0.2885 0.9884 0.3241 0.045 Uiso 1 1 calc R . .
C15 C 0.3734(3) 0.92374(16) 0.1723(5) 0.0327(8) Uani 1 1 d . . .
C16 C 0.3796(3) 0.97596(18) 0.0358(5) 0.0428(10) Uani 1 1 d . A .
H16A H 0.3057 1.0011 0.0284 0.051 Uiso 1 1 calc R . .
H16B H 0.4398 1.0108 0.0604 0.051 Uiso 1 1 calc R . .
C17 C 0.4055(4) 0.9425(2) -0.1253(5) 0.0492(11) Uani 1 1 d . . .
H17A H 0.3376 0.9163 -0.1632 0.059 Uiso 1 1 calc R A .
H17B H 0.4228 0.9794 -0.2056 0.059 Uiso 1 1 calc R . .
C18 C 0.5057(3) 0.8938(2) -0.1111(5) 0.0513(11) Uani 1 1 d . A .
H18A H 0.5730 0.9198 -0.0702 0.062 Uiso 1 1 calc R . .
H18B H 0.5251 0.8749 -0.2188 0.062 Uiso 1 1 calc R . .
C19 C 0.4779(3) 0.83385(19) 0.0030(5) 0.0390(9) Uani 1 1 d . . .
H19A H 0.4276 0.8001 -0.0535 0.047 Uiso 1 1 calc R A .
H19B H 0.5498 0.8092 0.0308 0.047 Uiso 1 1 calc R . .
C20 C 0.4197(3) 0.85670(16) 0.1570(5) 0.0294(7) Uani 1 1 d . A .
N1 N 0.4464(2) 0.73919(12) 0.2749(4) 0.0296(6) Uani 1 1 d . A .
O1 O 0.3059(2) 0.71450(12) 0.0948(3) 0.0424(7) Uani 1 1 d . A .
O2 O 0.4933(2) 0.64665(13) 0.4359(3) 0.0369(6) Uani 1 1 d . A .
Cl2 Cl 0.28164(9) 0.55951(5) 0.14965(17) 0.0619(3) Uani 1 1 d . . .
Cl3 Cl 0.61349(7) 0.64593(5) 0.07474(13) 0.0501(3) 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 1.31(3) . ?
C1 Cl2 1.608(7) . ?
C1 Cl1 1.688(9) . ?
C2 C3 1.514(11) . ?
C2 Cl3 1.84(3) . ?
C1' C2' 1.31(5) . ?
C1' Cl3 1.538(11) . ?
C1' Cl1' 1.732(18) . ?
C2' C3 1.56(2) . ?
C2' Cl2 1.84(5) . ?
C3 O1 1.205(4) . ?
C3 N1 1.383(5) . ?
C4 O2 1.210(4) . ?
C4 N1 1.429(5) . ?
C4 C5 1.481(5) . ?
C5 C10 1.394(5) . ?
C5 C6 1.399(5) . ?
C6 C7 1.381(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.373(5) . ?
C11 C20 1.398(5) . ?
C11 N1 1.449(4) . ?
C12 C13 1.391(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(6) . ?
C14 H14 0.9500 . ?
C15 C20 1.397(4) . ?
C15 C16 1.511(5) . ?
C16 C17 1.512(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.500(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.522(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.512(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 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 Cl2 119.7(12) . . ?
C2 C1 Cl1 126.5(11) . . ?
Cl2 C1 Cl1 113.5(7) . . ?
C1 C2 C3 122(2) . . ?
C1 C2 Cl3 120.8(9) . . ?
C3 C2 Cl3 117.4(16) . . ?
C2' C1' Cl3 124(2) . . ?
C2' C1' Cl1' 120.8(18) . . ?
Cl3 C1' Cl1' 115.3(13) . . ?
C1' C2' C3 116(3) . . ?
C1' C2' Cl2 124.7(17) . . ?
C3 C2' Cl2 118(2) . . ?
O1 C3 N1 122.4(3) . . ?
O1 C3 C2 123.1(8) . . ?
N1 C3 C2 113.5(9) . . ?
O1 C3 C2' 109.4(10) . . ?
N1 C3 C2' 126.8(7) . . ?
C2 C3 C2' 26.7(8) . . ?
O2 C4 N1 119.7(3) . . ?
O2 C4 C5 121.9(3) . . ?
N1 C4 C5 118.5(3) . . ?
C10 C5 C6 120.4(3) . . ?
C10 C5 C4 123.1(3) . . ?
C6 C5 C4 116.3(3) . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 119.2(4) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 119.0(4) . . ?
C9 C10 H10 120.5 . . ?
C5 C10 H10 120.5 . . ?
C12 C11 C20 122.5(3) . . ?
C12 C11 N1 117.1(3) . . ?
C20 C11 N1 120.3(3) . . ?
C11 C12 C13 119.3(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 122.0(3) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C20 119.5(3) . . ?
C14 C15 C16 119.2(3) . . ?
C20 C15 C16 121.3(3) . . ?
C17 C16 C15 113.1(3) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 110.4(4) . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 110.5(3) . . ?
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 . . ?
C20 C19 C18 113.8(3) . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C15 C20 C11 117.6(3) . . ?
C15 C20 C19 121.0(3) . . ?
C11 C20 C19 121.3(3) . . ?
C3 N1 C4 119.0(3) . . ?
C3 N1 C11 116.6(3) . . ?
C4 N1 C11 120.8(3) . . ?
C1 Cl2 C2' 30.6(8) . . ?
C1' Cl3 C2 30.4(7) . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.16
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.195
_refine_diff_density_min   -0.238
_refine_diff_density_rms    0.055
