 
data_422 
 
_audit_creation_method            SHELXTL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 'C21 H14 Cl3 N O2' 
_chemical_formula_sum 
 'C21 H14 Cl3 N O2' 
_chemical_formula_weight          418.68 
 
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' 
 '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            monoclinic 
_symmetry_space_group_name_H-M    'P 1 21/c 1' 
 
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                    11.4480(3) 
_cell_length_b                    7.4883(2) 
_cell_length_c                    21.7720(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  102.590(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1821.55(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150.0(1) 
_cell_measurement_reflns_used     4776 
_cell_measurement_theta_min       2.88 
_cell_measurement_theta_max       33.92 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           .31 
_exptl_crystal_size_mid           .25 
_exptl_crystal_size_min           .20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.527 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              856 
_exptl_absorpt_coefficient_mu     0.520 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   .878 
_exptl_absorpt_correction_T_max   1. 
_exptl_absorpt_process_details    SCALE3 
 
_exptl_special_details 
; 
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
 
; 
 
_diffrn_ambient_temperature 150.01(10) 
_diffrn_radiation_wavelength 0.7107
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator 'graphite'
_diffrn_measurement_device_type 'Xcalibur, Eos'
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  16.2060 
_diffrn_standards_number          15441 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             14246 
_diffrn_reflns_av_R_equivalents   0.0214 
_diffrn_reflns_av_sigmaI/netI     0.0323 
_diffrn_reflns_limit_h_min        -17 
_diffrn_reflns_limit_h_max        17 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        8 
_diffrn_reflns_limit_l_min        -32 
_diffrn_reflns_limit_l_max        23 
_diffrn_reflns_theta_min          2.88 
_diffrn_reflns_theta_max          32.07 
_reflns_number_total              6352 
_reflns_number_gt                 5089 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'BRUKER XSCANS' 
_computing_cell_refinement        'BRUKER XSCANS' 
_computing_data_reduction         'BRUKER SHELXTL' 
_computing_structure_solution     'BRUKER SHELXTL' 
_computing_structure_refinement   'BRUKER SHELXTL' 
_computing_molecular_graphics     'BRUKER SHELXTL' 
_computing_publication_material   'BRUKER SHELXTL' 
 
_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)+(0.0469P)²+0.4900P] 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      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          6352 
_refine_ls_number_parameters      247 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0534 
_refine_ls_R_factor_gt            0.0385 
_refine_ls_wR_factor_ref          0.1003 
_refine_ls_wR_factor_gt           0.0928 
_refine_ls_goodness_of_fit_ref    1.027 
_refine_ls_restrained_S_all       1.027 
_refine_ls_shift/su_max           0.001 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Cl1 Cl 0.58880(3) 1.11157(5) 0.096133(17) 0.02831(9) Uani 1 1 d . . . 
Cl2 Cl 0.59359(3) 0.87611(5) 0.214760(17) 0.02818(9) Uani 1 1 d . . . 
Cl3 Cl 0.37015(3) 0.87180(5) 0.272926(15) 0.02710(9) Uani 1 1 d . . . 
O1 O 0.18565(9) 1.11543(14) 0.20048(5) 0.0245(2) Uani 1 1 d . . . 
O2 O 0.19276(8) 0.89180(13) 0.00172(4) 0.02127(19) Uani 1 1 d . . . 
N1 N 0.01265(9) 0.79773(15) 0.04218(5) 0.0176(2) Uani 1 1 d . . . 
H1 H 0.0538(15) 0.804(2) 0.0137(8) 0.021 Uiso 1 1 d . . . 
C1 C 0.23661(11) 1.02072(17) 0.16901(6) 0.0169(2) Uani 1 1 d . . . 
C2 C 0.17980(11) 0.94509(17) 0.10742(6) 0.0158(2) Uani 1 1 d . . . 
C3 C 0.24078(11) 0.94606(17) 0.05584(6) 0.0166(2) Uani 1 1 d . . . 
C4 C 0.36076(11) 1.02537(17) 0.06089(6) 0.0186(2) Uani 1 1 d . . . 
H4 H 0.3724 1.0829 0.0249 0.022 Uiso 1 1 calc R . . 
C5 C 0.45518(11) 1.02671(17) 0.10960(6) 0.0184(2) Uani 1 1 d . . . 
C6 C 0.45851(11) 0.95969(17) 0.17311(6) 0.0184(2) Uani 1 1 d . . . 
C7 C 0.36192(11) 0.95643(17) 0.19855(6) 0.0179(2) Uani 1 1 d . . . 
C8 C 0.06338(11) 0.87175(17) 0.09750(6) 0.0164(2) Uani 1 1 d . . . 
C9 C -0.02180(11) 0.84623(19) 0.14260(6) 0.0205(2) Uani 1 1 d . . . 
C10 C -0.11555(12) 0.72542(19) 0.10348(6) 0.0219(3) Uani 1 1 d . . . 
C11 C -0.21680(13) 0.6452(2) 0.11856(8) 0.0289(3) Uani 1 1 d . . . 
H11 H -0.2306 0.6535 0.1590 0.035 Uiso 1 1 calc R . . 
C12 C -0.29471(13) 0.5546(2) 0.07222(8) 0.0315(3) Uani 1 1 d . . . 
H12 H -0.3609 0.4986 0.0820 0.038 Uiso 1 1 calc R . . 
C13 C -0.27699(12) 0.54394(18) 0.00976(8) 0.0260(3) Uani 1 1 d . . . 
C14 C -0.36213(13) 0.4613(2) -0.03946(8) 0.0321(3) Uani 1 1 d . . . 
H14 H -0.4292 0.4065 -0.0303 0.039 Uiso 1 1 calc R . . 
C15 C -0.34688(14) 0.4612(2) -0.09987(9) 0.0346(4) Uani 1 1 d . . . 
H15 H -0.4056 0.4119 -0.1317 0.042 Uiso 1 1 calc R . . 
C16 C -0.24276(14) 0.5355(2) -0.11467(8) 0.0306(3) Uani 1 1 d . . . 
H16 H -0.2327 0.5325 -0.1559 0.037 Uiso 1 1 calc R . . 
C17 C -0.15628(13) 0.61204(18) -0.06831(7) 0.0244(3) Uani 1 1 d . . . 
H17 H -0.0871 0.6581 -0.0780 0.029 Uiso 1 1 calc R . . 
C18 C -0.17271(12) 0.62063(17) -0.00585(7) 0.0213(3) Uani 1 1 d . . . 
C19 C -0.09444(11) 0.70869(17) 0.04408(6) 0.0190(2) Uani 1 1 d . . . 
C20 C -0.08405(12) 1.0254(2) 0.15118(7) 0.0253(3) Uani 1 1 d . . . 
H20A H -0.0270 1.1055 0.1758 0.038 Uiso 1 1 calc R . . 
H20B H -0.1481 1.0041 0.1723 0.038 Uiso 1 1 calc R . . 
H20C H -0.1156 1.0776 0.1107 0.038 Uiso 1 1 calc R . . 
C21 C 0.03578(13) 0.7619(2) 0.20607(7) 0.0315(3) Uani 1 1 d . . . 
H21A H 0.0945 0.8421 0.2294 0.047 Uiso 1 1 calc R . . 
H21B H 0.0736 0.6516 0.1992 0.047 Uiso 1 1 calc R . . 
H21C H -0.0247 0.7392 0.2295 0.047 Uiso 1 1 calc R . . 
 
 
_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 C5 1.7393(13) . ? 
Cl2 C6 1.7303(12) . ? 
Cl3 C7 1.7222(13) . ? 
O1 C1 1.2194(16) . ? 
O2 C3 1.2543(15) . ? 
N1 C8 1.3381(16) . ? 
N1 C19 1.4040(16) . ? 
N1 H1 0.857(18) . ? 
C1 C2 1.4702(17) . ? 
C1 C7 1.5170(17) . ? 
C2 C8 1.4139(17) . ? 
C2 C3 1.4459(17) . ? 
C3 C4 1.4783(18) . ? 
C4 C5 1.3391(18) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.4636(18) . ? 
C6 C7 1.3407(18) . ? 
C8 C9 1.5391(18) . ? 
C9 C10 1.5156(19) . ? 
C9 C21 1.5316(19) . ? 
C9 C20 1.549(2) . ? 
C10 C19 1.3722(19) . ? 
C10 C11 1.4064(19) . ? 
C11 C12 1.372(2) . ? 
C11 H11 0.9300 . ? 
C12 C13 1.420(2) . ? 
C12 H12 0.9300 . ? 
C13 C14 1.423(2) . ? 
C13 C18 1.431(2) . ? 
C14 C15 1.364(3) . ? 
C14 H14 0.9300 . ? 
C15 C16 1.415(2) . ? 
C15 H15 0.9300 . ? 
C16 C17 1.3754(19) . ? 
C16 H16 0.9300 . ? 
C17 C18 1.414(2) . ? 
C17 H17 0.9300 . ? 
C18 C19 1.4123(18) . ? 
C20 H20A 0.9600 . ? 
C20 H20B 0.9600 . ? 
C20 H20C 0.9600 . ? 
C21 H21A 0.9600 . ? 
C21 H21B 0.9600 . ? 
C21 H21C 0.9600 . ? 
 
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 
C8 N1 C19 112.37(11) . . ? 
C8 N1 H1 115.4(11) . . ? 
C19 N1 H1 131.9(11) . . ? 
O1 C1 C2 124.45(11) . . ? 
O1 C1 C7 118.05(11) . . ? 
C2 C1 C7 117.00(11) . . ? 
C8 C2 C3 118.81(11) . . ? 
C8 C2 C1 120.26(11) . . ? 
C3 C2 C1 120.92(11) . . ? 
O2 C3 C2 122.75(11) . . ? 
O2 C3 C4 114.20(11) . . ? 
C2 C3 C4 122.84(11) . . ? 
C5 C4 C3 129.68(12) . . ? 
C5 C4 H4 115.2 . . ? 
C3 C4 H4 115.2 . . ? 
C4 C5 C6 126.57(11) . . ? 
C4 C5 Cl1 117.19(10) . . ? 
C6 C5 Cl1 116.22(9) . . ? 
C7 C6 C5 122.86(11) . . ? 
C7 C6 Cl2 120.01(10) . . ? 
C5 C6 Cl2 117.09(9) . . ? 
C6 C7 C1 127.44(11) . . ? 
C6 C7 Cl3 120.95(10) . . ? 
C1 C7 Cl3 111.61(9) . . ? 
N1 C8 C2 120.54(11) . . ? 
N1 C8 C9 108.17(11) . . ? 
C2 C8 C9 131.14(11) . . ? 
C10 C9 C21 111.95(12) . . ? 
C10 C9 C8 100.67(10) . . ? 
C21 C9 C8 114.77(11) . . ? 
C10 C9 C20 107.26(10) . . ? 
C21 C9 C20 111.53(12) . . ? 
C8 C9 C20 109.96(11) . . ? 
C19 C10 C11 120.30(13) . . ? 
C19 C10 C9 109.60(11) . . ? 
C11 C10 C9 129.96(13) . . ? 
C12 C11 C10 118.44(15) . . ? 
C12 C11 H11 120.8 . . ? 
C10 C11 H11 120.8 . . ? 
C11 C12 C13 121.75(14) . . ? 
C11 C12 H12 119.1 . . ? 
C13 C12 H12 119.1 . . ? 
C12 C13 C14 121.86(14) . . ? 
C12 C13 C18 120.38(13) . . ? 
C14 C13 C18 117.74(15) . . ? 
C15 C14 C13 121.04(15) . . ? 
C15 C14 H14 119.5 . . ? 
C13 C14 H14 119.5 . . ? 
C14 C15 C16 120.71(14) . . ? 
C14 C15 H15 119.6 . . ? 
C16 C15 H15 119.6 . . ? 
C17 C16 C15 120.28(15) . . ? 
C17 C16 H16 119.9 . . ? 
C15 C16 H16 119.9 . . ? 
C16 C17 C18 119.94(14) . . ? 
C16 C17 H17 120.0 . . ? 
C18 C17 H17 120.0 . . ? 
C19 C18 C17 124.49(13) . . ? 
C19 C18 C13 115.27(13) . . ? 
C17 C18 C13 120.19(12) . . ? 
C10 C19 N1 108.59(11) . . ? 
C10 C19 C18 123.74(12) . . ? 
N1 C19 C18 127.63(12) . . ? 
C9 C20 H20A 109.5 . . ? 
C9 C20 H20B 109.5 . . ? 
H20A C20 H20B 109.5 . . ? 
C9 C20 H20C 109.5 . . ? 
H20A C20 H20C 109.5 . . ? 
H20B C20 H20C 109.5 . . ? 
C9 C21 H21A 109.5 . . ? 
C9 C21 H21B 109.5 . . ? 
H21A C21 H21B 109.5 . . ? 
C9 C21 H21C 109.5 . . ? 
H21A C21 H21C 109.5 . . ? 
H21B C21 H21C 109.5 . . ? 
 
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 C1 C2 C8 -42.66(19) . . . . ? 
C7 C1 C2 C8 129.12(12) . . . . ? 
O1 C1 C2 C3 136.59(14) . . . . ? 
C7 C1 C2 C3 -51.63(16) . . . . ? 
C8 C2 C3 O2 3.28(19) . . . . ? 
C1 C2 C3 O2 -175.98(11) . . . . ? 
C8 C2 C3 C4 177.79(11) . . . . ? 
C1 C2 C3 C4 -1.47(18) . . . . ? 
O2 C3 C4 C5 -148.32(14) . . . . ? 
C2 C3 C4 C5 36.7(2) . . . . ? 
C3 C4 C5 C6 -5.4(2) . . . . ? 
C3 C4 C5 Cl1 172.96(11) . . . . ? 
C4 C5 C6 C7 -28.6(2) . . . . ? 
Cl1 C5 C6 C7 153.01(11) . . . . ? 
C4 C5 C6 Cl2 149.47(12) . . . . ? 
Cl1 C5 C6 Cl2 -28.93(13) . . . . ? 
C5 C6 C7 C1 -1.1(2) . . . . ? 
Cl2 C6 C7 C1 -179.08(10) . . . . ? 
C5 C6 C7 Cl3 178.64(10) . . . . ? 
Cl2 C6 C7 Cl3 0.64(16) . . . . ? 
O1 C1 C7 C6 -132.61(15) . . . . ? 
C2 C1 C7 C6 55.07(18) . . . . ? 
O1 C1 C7 Cl3 47.65(15) . . . . ? 
C2 C1 C7 Cl3 -124.67(11) . . . . ? 
C19 N1 C8 C2 170.98(11) . . . . ? 
C19 N1 C8 C9 -5.11(14) . . . . ? 
C3 C2 C8 N1 2.82(18) . . . . ? 
C1 C2 C8 N1 -177.92(11) . . . . ? 
C3 C2 C8 C9 177.88(12) . . . . ? 
C1 C2 C8 C9 -2.9(2) . . . . ? 
N1 C8 C9 C10 7.34(13) . . . . ? 
C2 C8 C9 C10 -168.18(13) . . . . ? 
N1 C8 C9 C21 127.72(13) . . . . ? 
C2 C8 C9 C21 -47.8(2) . . . . ? 
N1 C8 C9 C20 -105.59(12) . . . . ? 
C2 C8 C9 C20 78.89(16) . . . . ? 
C21 C9 C10 C19 -129.67(13) . . . . ? 
C8 C9 C10 C19 -7.29(14) . . . . ? 
C20 C9 C10 C19 107.68(13) . . . . ? 
C21 C9 C10 C11 54.6(2) . . . . ? 
C8 C9 C10 C11 176.93(14) . . . . ? 
C20 C9 C10 C11 -68.09(18) . . . . ? 
C19 C10 C11 C12 -1.6(2) . . . . ? 
C9 C10 C11 C12 173.77(14) . . . . ? 
C10 C11 C12 C13 -1.6(2) . . . . ? 
C11 C12 C13 C14 -175.29(15) . . . . ? 
C11 C12 C13 C18 3.3(2) . . . . ? 
C12 C13 C14 C15 176.25(15) . . . . ? 
C18 C13 C14 C15 -2.4(2) . . . . ? 
C13 C14 C15 C16 3.3(2) . . . . ? 
C14 C15 C16 C17 -1.2(2) . . . . ? 
C15 C16 C17 C18 -1.6(2) . . . . ? 
C16 C17 C18 C19 -174.69(13) . . . . ? 
C16 C17 C18 C13 2.3(2) . . . . ? 
C12 C13 C18 C19 -1.78(19) . . . . ? 
C14 C13 C18 C19 176.89(12) . . . . ? 
C12 C13 C18 C17 -179.07(13) . . . . ? 
C14 C13 C18 C17 -0.39(19) . . . . ? 
C11 C10 C19 N1 -178.90(12) . . . . ? 
C9 C10 C19 N1 4.85(15) . . . . ? 
C11 C10 C19 C18 3.2(2) . . . . ? 
C9 C10 C19 C18 -173.04(12) . . . . ? 
C8 N1 C19 C10 0.24(15) . . . . ? 
C8 N1 C19 C18 178.03(12) . . . . ? 
C17 C18 C19 C10 175.73(13) . . . . ? 
C13 C18 C19 C10 -1.43(19) . . . . ? 
C17 C18 C19 N1 -1.8(2) . . . . ? 
C13 C18 C19 N1 -178.91(12) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              32.07 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.431 
_refine_diff_density_min   -0.340 
_refine_diff_density_rms    0.060 
