
data_c:\dumi07\659bis\659biss 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 '3-(4-chlorobenzoyl)-pyrrolo[1,2-c]quinazoline-1-carboxylate' 
; 
_chemical_name_common             none 
_chemical_melting_point           '185-187C' 
_chemical_formula_moiety          'C21 H15 Cl N2 O3' 
_chemical_formula_sum 
 'C21 H15 Cl N2 O3' 
_chemical_formula_weight          378.80 
 
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            triclinic 
_symmetry_space_group_name_H-M    P-1 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    8.1761(4) 
_cell_length_b                    9.2255(4) 
_cell_length_c                    11.5258(4) 
_cell_angle_alpha                 92.014(3) 
_cell_angle_beta                  90.871(3) 
_cell_angle_gamma                 99.323(2) 
_cell_volume                      857.17(6) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     4746 
_cell_measurement_theta_min       1.00 
_cell_measurement_theta_max       28.28 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.12 
_exptl_crystal_size_mid           0.08 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.468 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              392 
_exptl_absorpt_coefficient_mu     0.249 
_exptl_absorpt_correction_type    'analytical' 
_exptl_absorpt_correction_T_min   0.9708 
_exptl_absorpt_correction_T_max   0.9816 
_exptl_absorpt_process_details    'face-indexing (program X-Prep)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius-Kappa CCD diffractometer' 
_diffrn_measurement_method        'phi-scan 1.0-2.0 deg; omega-scan 2.0 deg' 
_diffrn_reflns_number             25082 
_diffrn_reflns_av_R_equivalents   0.0359 
_diffrn_reflns_av_sigmaI/netI     0.0287 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          3.05 
_diffrn_reflns_theta_max          29.51 
_reflns_number_total              4746 
_reflns_number_gt                 3806 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT 2000' 
_computing_cell_refinement        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction         'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)' 
 
_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)+(0.0446P)²+0.2884P] 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          4746 
_refine_ls_number_parameters      245 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0517 
_refine_ls_R_factor_gt            0.0375 
_refine_ls_wR_factor_ref          0.0990 
_refine_ls_wR_factor_gt           0.0917 
_refine_ls_goodness_of_fit_ref    1.043 
_refine_ls_restrained_S_all       1.043 
_refine_ls_shift/su_max           0.000 
_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 
N1 N 0.40203(11) 0.66393(11) 0.50145(8) 0.0182(2) Uani 1 1 d . . . 
C2 C 0.36290(15) 0.66882(14) 0.61789(10) 0.0225(2) Uani 1 1 d . . . 
H2 H 0.2725 0.6001 0.6435 0.027 Uiso 1 1 calc R . . 
N3 N 0.44209(13) 0.76112(12) 0.69308(9) 0.0243(2) Uani 1 1 d . . . 
C4 C 0.57232(14) 0.86376(13) 0.65439(10) 0.0210(2) Uani 1 1 d . . . 
C5 C 0.62297(14) 0.86767(13) 0.53742(10) 0.0188(2) Uani 1 1 d . . . 
C6 C 0.53458(13) 0.75857(13) 0.45687(10) 0.0183(2) Uani 1 1 d . . . 
C7 C 0.53891(14) 0.72036(13) 0.33748(10) 0.0196(2) Uani 1 1 d . . . 
C8 C 0.40328(14) 0.60818(13) 0.31207(10) 0.0207(2) Uani 1 1 d . . . 
H8 H 0.3746 0.5638 0.2374 0.025 Uiso 1 1 calc R . . 
C9 C 0.31878(14) 0.57290(13) 0.41215(10) 0.0196(2) Uani 1 1 d . . . 
C10 C 0.65361(16) 0.96683(14) 0.73736(11) 0.0249(3) Uani 1 1 d . . . 
H10 H 0.6198 0.9636 0.8158 0.030 Uiso 1 1 calc R . . 
C11 C 0.78197(16) 1.07240(14) 0.70544(11) 0.0259(3) Uani 1 1 d . . . 
H11 H 0.8381 1.1405 0.7623 0.031 Uiso 1 1 calc R . . 
C12 C 0.83032(15) 1.07996(14) 0.58952(11) 0.0245(3) Uani 1 1 d . . . 
H12 H 0.9173 1.1547 0.5678 0.029 Uiso 1 1 calc R . . 
C13 C 0.75258(14) 0.97962(13) 0.50646(11) 0.0215(2) Uani 1 1 d . . . 
H13 H 0.7863 0.9858 0.4280 0.026 Uiso 1 1 calc R . . 
C14 C 0.65999(15) 0.77557(13) 0.25009(10) 0.0224(2) Uani 1 1 d . . . 
O15 O 0.79058(12) 0.85668(12) 0.26623(8) 0.0357(2) Uani 1 1 d . . . 
O16 O 0.60832(11) 0.71901(11) 0.14402(8) 0.0301(2) Uani 1 1 d . . . 
C17 C 0.71650(17) 0.76460(16) 0.04879(11) 0.0297(3) Uani 1 1 d . . . 
H17A H 0.8326 0.7570 0.0697 0.036 Uiso 1 1 calc R . . 
H17B H 0.7110 0.8678 0.0307 0.036 Uiso 1 1 calc R . . 
C18 C 0.65784(17) 0.66420(16) -0.05422(11) 0.0307(3) Uani 1 1 d . . . 
H18A H 0.6620 0.5623 -0.0348 0.046 Uiso 1 1 calc R . . 
H18B H 0.7297 0.6906 -0.1201 0.046 Uiso 1 1 calc R . . 
H18C H 0.5436 0.6742 -0.0750 0.046 Uiso 1 1 calc R . . 
C19 C 0.17770(14) 0.45636(12) 0.42858(10) 0.0188(2) Uani 1 1 d . . . 
O20 O 0.14257(11) 0.40258(10) 0.52268(7) 0.02496(19) Uani 1 1 d . . . 
C21 C 0.07817(14) 0.40083(13) 0.32101(10) 0.0188(2) Uani 1 1 d . . . 
C22 C 0.02971(15) 0.49650(13) 0.24119(11) 0.0229(2) Uani 1 1 d . . . 
H22 H 0.0632 0.5995 0.2529 0.027 Uiso 1 1 calc R . . 
C23 C -0.06755(16) 0.44178(14) 0.14433(11) 0.0254(3) Uani 1 1 d . . . 
H23 H -0.1029 0.5068 0.0907 0.030 Uiso 1 1 calc R . . 
C24 C -0.11188(15) 0.29134(15) 0.12746(11) 0.0247(3) Uani 1 1 d . . . 
C25 C -0.06624(15) 0.19379(14) 0.20578(11) 0.0246(3) Uani 1 1 d . . . 
H25 H -0.0982 0.0908 0.1928 0.029 Uiso 1 1 calc R . . 
C26 C 0.02730(14) 0.25000(13) 0.30377(10) 0.0213(2) Uani 1 1 d . . . 
H26 H 0.0568 0.1848 0.3595 0.026 Uiso 1 1 calc R . . 
Cl27 Cl -0.22969(5) 0.22339(4) 0.00442(3) 0.03878(11) 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 
N1 C2 1.3852(15) . ? 
N1 C6 1.3938(14) . ? 
N1 C9 1.4003(14) . ? 
C2 N3 1.2836(16) . ? 
C2 H2 0.9500 . ? 
N3 C4 1.3953(16) . ? 
C4 C10 1.4043(17) . ? 
C4 C5 1.4163(16) . ? 
C5 C13 1.4141(16) . ? 
C5 C6 1.4407(16) . ? 
C6 C7 1.4108(16) . ? 
C7 C8 1.4084(16) . ? 
C7 C14 1.4686(16) . ? 
C8 C9 1.3753(16) . ? 
C8 H8 0.9500 . ? 
C9 C19 1.4634(16) . ? 
C10 C11 1.3752(18) . ? 
C10 H10 0.9500 . ? 
C11 C12 1.3999(19) . ? 
C11 H11 0.9500 . ? 
C12 C13 1.3805(17) . ? 
C12 H12 0.9500 . ? 
C13 H13 0.9500 . ? 
C14 O15 1.2083(15) . ? 
C14 O16 1.3466(15) . ? 
O16 C17 1.4510(15) . ? 
C17 C18 1.5030(18) . ? 
C17 H17A 0.9900 . ? 
C17 H17B 0.9900 . ? 
C18 H18A 0.9800 . ? 
C18 H18B 0.9800 . ? 
C18 H18C 0.9800 . ? 
C19 O20 1.2272(14) . ? 
C19 C21 1.5005(16) . ? 
C21 C26 1.3926(16) . ? 
C21 C22 1.3934(17) . ? 
C22 C23 1.3917(17) . ? 
C22 H22 0.9500 . ? 
C23 C24 1.3825(19) . ? 
C23 H23 0.9500 . ? 
C24 C25 1.3855(19) . ? 
C24 Cl27 1.7413(13) . ? 
C25 C26 1.3905(17) . ? 
C25 H25 0.9500 . ? 
C26 H26 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 
C2 N1 C6 122.05(10) . . ? 
C2 N1 C9 127.84(10) . . ? 
C6 N1 C9 110.08(9) . . ? 
N3 C2 N1 123.57(11) . . ? 
N3 C2 H2 118.2 . . ? 
N1 C2 H2 118.2 . . ? 
C2 N3 C4 117.89(10) . . ? 
N3 C4 C10 116.94(11) . . ? 
N3 C4 C5 123.01(11) . . ? 
C10 C4 C5 120.05(11) . . ? 
C13 C5 C4 118.48(11) . . ? 
C13 C5 C6 124.31(11) . . ? 
C4 C5 C6 117.19(10) . . ? 
N1 C6 C7 106.35(10) . . ? 
N1 C6 C5 116.19(10) . . ? 
C7 C6 C5 137.41(11) . . ? 
C8 C7 C6 107.40(10) . . ? 
C8 C7 C14 122.66(10) . . ? 
C6 C7 C14 129.88(11) . . ? 
C9 C8 C7 109.48(10) . . ? 
C9 C8 H8 125.3 . . ? 
C7 C8 H8 125.3 . . ? 
C8 C9 N1 106.60(10) . . ? 
C8 C9 C19 128.47(11) . . ? 
N1 C9 C19 124.76(10) . . ? 
C11 C10 C4 120.27(12) . . ? 
C11 C10 H10 119.9 . . ? 
C4 C10 H10 119.9 . . ? 
C10 C11 C12 120.26(11) . . ? 
C10 C11 H11 119.9 . . ? 
C12 C11 H11 119.9 . . ? 
C13 C12 C11 120.52(12) . . ? 
C13 C12 H12 119.7 . . ? 
C11 C12 H12 119.7 . . ? 
C12 C13 C5 120.39(11) . . ? 
C12 C13 H13 119.8 . . ? 
C5 C13 H13 119.8 . . ? 
O15 C14 O16 122.36(11) . . ? 
O15 C14 C7 127.46(11) . . ? 
O16 C14 C7 110.16(10) . . ? 
C14 O16 C17 116.11(10) . . ? 
O16 C17 C18 107.19(11) . . ? 
O16 C17 H17A 110.3 . . ? 
C18 C17 H17A 110.3 . . ? 
O16 C17 H17B 110.3 . . ? 
C18 C17 H17B 110.3 . . ? 
H17A C17 H17B 108.5 . . ? 
C17 C18 H18A 109.5 . . ? 
C17 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
C17 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
O20 C19 C9 123.51(11) . . ? 
O20 C19 C21 120.70(10) . . ? 
C9 C19 C21 115.76(10) . . ? 
C26 C21 C22 119.52(11) . . ? 
C26 C21 C19 118.75(10) . . ? 
C22 C21 C19 121.66(10) . . ? 
C23 C22 C21 120.30(11) . . ? 
C23 C22 H22 119.9 . . ? 
C21 C22 H22 119.9 . . ? 
C24 C23 C22 118.94(11) . . ? 
C24 C23 H23 120.5 . . ? 
C22 C23 H23 120.5 . . ? 
C23 C24 C25 121.94(11) . . ? 
C23 C24 Cl27 118.74(10) . . ? 
C25 C24 Cl27 119.33(10) . . ? 
C24 C25 C26 118.55(11) . . ? 
C24 C25 H25 120.7 . . ? 
C26 C25 H25 120.7 . . ? 
C25 C26 C21 120.69(11) . . ? 
C25 C26 H26 119.7 . . ? 
C21 C26 H26 119.7 . . ? 
 
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 
C6 N1 C2 N3 1.30(18) . . . . ? 
C9 N1 C2 N3 -176.58(12) . . . . ? 
N1 C2 N3 C4 1.38(18) . . . . ? 
C2 N3 C4 C10 177.90(11) . . . . ? 
C2 N3 C4 C5 -1.73(18) . . . . ? 
N3 C4 C5 C13 177.74(11) . . . . ? 
C10 C4 C5 C13 -1.88(17) . . . . ? 
N3 C4 C5 C6 -0.52(17) . . . . ? 
C10 C4 C5 C6 179.85(11) . . . . ? 
C2 N1 C6 C7 178.84(10) . . . . ? 
C9 N1 C6 C7 -2.94(12) . . . . ? 
C2 N1 C6 C5 -3.48(16) . . . . ? 
C9 N1 C6 C5 174.74(10) . . . . ? 
C13 C5 C6 N1 -175.17(10) . . . . ? 
C4 C5 C6 N1 2.98(15) . . . . ? 
C13 C5 C6 C7 1.5(2) . . . . ? 
C4 C5 C6 C7 179.69(13) . . . . ? 
N1 C6 C7 C8 2.89(13) . . . . ? 
C5 C6 C7 C8 -174.03(13) . . . . ? 
N1 C6 C7 C14 -174.61(12) . . . . ? 
C5 C6 C7 C14 8.5(2) . . . . ? 
C6 C7 C8 C9 -1.85(14) . . . . ? 
C14 C7 C8 C9 175.87(11) . . . . ? 
C7 C8 C9 N1 0.05(13) . . . . ? 
C7 C8 C9 C19 -175.32(11) . . . . ? 
C2 N1 C9 C8 179.91(11) . . . . ? 
C6 N1 C9 C8 1.82(13) . . . . ? 
C2 N1 C9 C19 -4.50(19) . . . . ? 
C6 N1 C9 C19 177.41(10) . . . . ? 
N3 C4 C10 C11 -179.29(11) . . . . ? 
C5 C4 C10 C11 0.35(18) . . . . ? 
C4 C10 C11 C12 1.37(19) . . . . ? 
C10 C11 C12 C13 -1.53(19) . . . . ? 
C11 C12 C13 C5 -0.05(18) . . . . ? 
C4 C5 C13 C12 1.73(17) . . . . ? 
C6 C5 C13 C12 179.86(11) . . . . ? 
C8 C7 C14 O15 -169.62(13) . . . . ? 
C6 C7 C14 O15 7.5(2) . . . . ? 
C8 C7 C14 O16 8.53(16) . . . . ? 
C6 C7 C14 O16 -174.30(12) . . . . ? 
O15 C14 O16 C17 -1.80(19) . . . . ? 
C7 C14 O16 C17 179.93(11) . . . . ? 
C14 O16 C17 C18 167.05(11) . . . . ? 
C8 C9 C19 O20 156.38(12) . . . . ? 
N1 C9 C19 O20 -18.22(18) . . . . ? 
C8 C9 C19 C21 -21.74(17) . . . . ? 
N1 C9 C19 C21 163.65(11) . . . . ? 
O20 C19 C21 C26 -41.06(16) . . . . ? 
C9 C19 C21 C26 137.13(11) . . . . ? 
O20 C19 C21 C22 136.08(12) . . . . ? 
C9 C19 C21 C22 -45.73(15) . . . . ? 
C26 C21 C22 C23 -0.59(18) . . . . ? 
C19 C21 C22 C23 -177.71(11) . . . . ? 
C21 C22 C23 C24 -1.43(19) . . . . ? 
C22 C23 C24 C25 1.84(19) . . . . ? 
C22 C23 C24 Cl27 -178.58(10) . . . . ? 
C23 C24 C25 C26 -0.19(19) . . . . ? 
Cl27 C24 C25 C26 -179.76(9) . . . . ? 
C24 C25 C26 C21 -1.90(18) . . . . ? 
C22 C21 C26 C25 2.29(17) . . . . ? 
C19 C21 C26 C25 179.49(11) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.992 
_diffrn_reflns_theta_full              29.51 
_diffrn_measured_fraction_theta_full   0.992 
_refine_diff_density_max    0.313 
_refine_diff_density_min   -0.337 
_refine_diff_density_rms    0.048

#============================================

