# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 207/497
 
data_omc0002 
  
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C22 H22 Cl2 N4 O' 
_chemical_formula_weight          429.34 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Cl'  'Cl'   0.3639   0.7018 
 '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 
  
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                    9.667(3) 
_cell_length_b                    14.060(2) 
_cell_length_c                    17.366(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  105.90(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      2270.0(8) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     24 
_cell_measurement_theta_min       6.26 
_cell_measurement_theta_max       26.03 
  
_exptl_crystal_description        blocks 
_exptl_crystal_colour             Colourless 
_exptl_crystal_size_max           .33 
_exptl_crystal_size_mid           .30 
_exptl_crystal_size_min           .17 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.256 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              896 
_exptl_absorpt_coefficient_mu     2.726 
_exptl_absorpt_correction_type    empirical 
_exptl_absorpt_correction_T_min   0.4277 
_exptl_absorpt_correction_T_max   0.6303 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Siemens P4' 
_diffrn_measurement_method        '\w scans' 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  97 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             3787 
_diffrn_reflns_av_R_equivalents   0.0242 
_diffrn_reflns_av_sigmaI/netI     0.0325 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          4.11 
_diffrn_reflns_theta_max          61.98 
_reflns_number_total              3555 
_reflns_number_observed           2771 
_reflns_observed_criterion        >2sigma(I) 
  
_computing_data_collection        'Siemens XSCANS' 
_computing_cell_refinement        'Siemens XSCANS' 
_computing_data_reduction         'Siemens SHELXTL' 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'Siemens SHELXTL' 
_computing_publication_material   'Siemens SHELXTL' 
  
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 225 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses of fit S are based on F^2^, conventional R-factors R 
 are based on F, with F set to zero for negative F^2^. The observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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 w=1/[\s^2^(Fo^2^)+(0.0801P)^2^+0.9842P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     ? 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0013(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          3330 
_refine_ls_number_parameters      270 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0743 
_refine_ls_R_factor_obs           0.0579 
_refine_ls_wR_factor_all          0.1738 
_refine_ls_wR_factor_obs          0.1508 
_refine_ls_goodness_of_fit_all    1.051 
_refine_ls_goodness_of_fit_obs    1.096 
_refine_ls_restrained_S_all       1.106 
_refine_ls_restrained_S_obs       1.095 
_refine_ls_shift/esd_max          -0.015 
_refine_ls_shift/esd_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
Cl1 Cl 0.5861(2) 0.88674(12) 0.46256(9) 0.1193(5) Uani 1 d . . 
Cl2 Cl 0.63058(12) 0.97268(8) 0.08582(6) 0.0856(4) Uani 1 d . . 
C1 C 0.8009(3) 0.7345(2) 0.3380(2) 0.0505(7) Uani 1 d . . 
C2 C 0.7171(3) 0.6520(3) 0.3176(2) 0.0606(8) Uani 1 d . . 
N2 N 0.7655(4) 0.5789(2) 0.2737(2) 0.0751(8) Uani 1 d . . 
C3 C 0.5909(4) 0.6446(3) 0.3421(2) 0.0825(12) Uani 1 d . . 
H3A H 0.5340(4) 0.5904(3) 0.3288(2) 0.099 Uiso 1 calc R . 
C4 C 0.5491(4) 0.7161(4) 0.3857(3) 0.0870(13) Uani 1 d . . 
H4A H 0.4648(4) 0.7102(4) 0.4012(3) 0.104 Uiso 1 calc R . 
C5 C 0.6335(4) 0.7959(3) 0.4058(2) 0.0733(10) Uani 1 d . . 
C6 C 0.9337(3) 0.7478(2) 0.3079(2) 0.0461(6) Uani 1 d . . 
H6A H 0.9823(3) 0.6861(2) 0.3109(2) 0.055 Uiso 1 calc R . 
C6 C 0.7583(4) 0.8052(3) 0.3825(2) 0.0605(8) Uani 1 d . . 
H6B H 0.8146(4) 0.8594(3) 0.3968(2) 0.073 Uiso 1 calc R . 
C8 C 0.8938(3) 0.7810(2) 0.2207(2) 0.0454(6) Uani 1 d . . 
C9 C 0.9601(3) 0.7426(2) 0.1660(2) 0.0494(6) Uani 1 d . . 
C10 C 0.9289(4) 0.7778(2) 0.0878(2) 0.0615(8) Uani 1 d . . 
H10A H 0.9761(4) 0.7531(2) 0.0522(2) 0.074 Uiso 1 calc R . 
C11 C 0.8284(4) 0.8487(3) 0.0633(2) 0.0641(8) Uani 1 d . . 
H11A H 0.8067(4) 0.8719(3) 0.0112(2) 0.077 Uiso 1 calc R . 
C12 C 0.7607(3) 0.8848(2) 0.1167(2) 0.0568(7) Uani 1 d . . 
C13 C 0.7931(3) 0.8527(2) 0.1949(2) 0.0516(7) Uani 1 d . . 
H13A H 0.7473(3) 0.8794(2) 0.2303(2) 0.062 Uiso 1 calc R . 
N14 N 1.0367(3) 0.8163(2) 0.35509(14) 0.0529(6) Uani 1 d D . 
H14 H 1.0055(40) 0.8768(9) 0.3531(23) 0.073(11) Uiso 1 d D . 
C15 C 1.1298(3) 0.7918(3) 0.4278(2) 0.0567(8) Uani 1 d . . 
N16 N 1.1518(4) 0.6991(2) 0.4440(2) 0.0748(9) Uani 1 d . . 
C17 C 1.2510(5) 0.6774(4) 0.5136(2) 0.098(2) Uani 1 d . . 
H17A H 1.2691(5) 0.6135(4) 0.5262(2) 0.118 Uiso 1 calc R . 
C18 C 1.3260(5) 0.7437(5) 0.5663(2) 0.104(2) Uani 1 d . . 
H18A H 1.3953(5) 0.7251(5) 0.6124(2) 0.125 Uiso 1 calc R . 
C19 C 1.2970(5) 0.8379(5) 0.5498(3) 0.103(2) Uani 1 d . . 
H19A H 1.3438(5) 0.8842(5) 0.5858(3) 0.124 Uiso 1 calc R . 
C20 C 1.1991(4) 0.8638(3) 0.4803(2) 0.0803(11) Uani 1 d . . 
H20A H 1.1787(4) 0.9275(3) 0.4680(2) 0.096 Uiso 1 calc R . 
C21 C 0.8659(8) 0.5121(4) 0.3249(4) 0.122(2) Uani 1 d . . 
H21A H 0.9428(29) 0.5467(4) 0.3606(20) 0.182 Uiso 1 calc R . 
H21B H 0.9047(41) 0.4705(23) 0.2921(4) 0.182 Uiso 1 calc R . 
H21C H 0.8162(14) 0.4752(24) 0.3554(22) 0.182 Uiso 1 calc R . 
C22 C 0.6543(8) 0.5321(6) 0.2124(4) 0.162(3) Uani 1 d . . 
H22A H 0.5992(49) 0.5788(7) 0.1766(25) 0.243 Uiso 1 calc R . 
H22B H 0.5923(47) 0.4973(42) 0.2370(5) 0.243 Uiso 1 calc R . 
H22C H 0.6978(8) 0.4890(38) 0.1830(28) 0.243 Uiso 1 calc R . 
N23 N 1.0586(3) 0.6648(2) 0.1873(2) 0.0574(6) Uani 1 d . . 
C23 C 1.2026(4) 0.6777(3) 0.2414(2) 0.0721(9) Uani 1 d . . 
H23A H 1.2676(8) 0.6333(15) 0.2277(12) 0.108 Uiso 1 calc R . 
H23B H 1.1999(8) 0.6667(22) 0.2955(3) 0.108 Uiso 1 calc R . 
H23C H 1.2348(14) 0.7414(7) 0.2365(14) 0.108 Uiso 1 calc R . 
C24 C 1.0191(5) 0.5810(3) 0.1526(2) 0.0767(10) Uani 1 d . . 
H24A H 0.9279(5) 0.5768(3) 0.1170(2) 0.092 Uiso 1 calc R . 
O24 O 1.0927(4) 0.5095(2) 0.1637(2) 0.1001(10) Uani 1 d . . 
  
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
Cl1 0.1255(10) 0.1346(11) 0.1262(10) -0.0007(8) 0.0823(9) 0.0318(8) 
Cl2 0.0939(7) 0.0800(6) 0.0741(6) 0.0183(5) 0.0082(5) 0.0330(5) 
C1 0.0505(15) 0.057(2) 0.0446(14) 0.0113(12) 0.0144(12) 0.0002(13) 
C2 0.057(2) 0.071(2) 0.050(2) 0.0107(15) 0.0090(13) -0.0111(15) 
N2 0.085(2) 0.065(2) 0.070(2) -0.0043(14) 0.013(2) -0.015(2) 
C3 0.065(2) 0.103(3) 0.077(2) 0.011(2) 0.016(2) -0.026(2) 
C4 0.057(2) 0.130(4) 0.081(3) 0.018(3) 0.030(2) -0.005(2) 
C5 0.067(2) 0.093(3) 0.069(2) 0.015(2) 0.034(2) 0.012(2) 
C6 0.0503(15) 0.0462(14) 0.0423(14) 0.0048(11) 0.0136(11) -0.0001(12) 
C6 0.063(2) 0.066(2) 0.059(2) 0.0084(15) 0.0265(15) 0.0018(15) 
C8 0.0511(14) 0.0439(13) 0.0415(14) 0.0025(11) 0.0132(11) -0.0020(11) 
C9 0.0519(15) 0.050(2) 0.0453(14) -0.0007(12) 0.0124(12) 0.0018(12) 
C10 0.073(2) 0.069(2) 0.045(2) -0.0016(14) 0.0191(14) 0.005(2) 
C11 0.077(2) 0.070(2) 0.0414(15) 0.0066(14) 0.0094(14) 0.006(2) 
C12 0.061(2) 0.053(2) 0.050(2) 0.0076(13) 0.0059(13) 0.0048(14) 
C13 0.056(2) 0.052(2) 0.0464(15) 0.0020(12) 0.0132(12) 0.0050(13) 
N14 0.0542(14) 0.0574(15) 0.0453(13) 0.0027(11) 0.0108(10) -0.0035(11) 
C15 0.0479(15) 0.083(2) 0.0417(15) 0.0018(14) 0.0168(12) -0.0010(15) 
N16 0.087(2) 0.089(2) 0.0466(14) 0.0075(14) 0.0143(14) 0.026(2) 
C17 0.109(3) 0.124(4) 0.059(2) 0.017(2) 0.020(2) 0.052(3) 
C18 0.078(3) 0.173(6) 0.051(2) 0.002(3) 0.000(2) 0.021(3) 
C19 0.081(3) 0.156(5) 0.063(2) -0.002(3) 0.003(2) -0.022(3) 
C20 0.078(2) 0.100(3) 0.058(2) 0.001(2) 0.010(2) -0.026(2) 
C21 0.180(6) 0.071(3) 0.123(4) 0.018(3) 0.057(4) 0.023(3) 
C22 0.137(5) 0.190(8) 0.150(6) -0.092(6) 0.023(5) -0.052(5) 
N23 0.0623(15) 0.0537(14) 0.0568(14) -0.0034(12) 0.0171(12) 0.0098(12) 
C23 0.058(2) 0.086(2) 0.071(2) -0.001(2) 0.015(2) 0.018(2) 
C24 0.089(3) 0.060(2) 0.079(2) -0.001(2) 0.019(2) 0.008(2) 
O24 0.120(2) 0.061(2) 0.119(2) -0.002(2) 0.033(2) 0.024(2) 
  
_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 1.749(4) . ? 
Cl2 C12 1.740(3) . ? 
C1 C6 1.389(5) . ? 
C1 C2 1.404(4) . ? 
C1 C6 1.524(4) . ? 
C2 C3 1.403(5) . ? 
C2 N2 1.431(5) . ? 
N2 C22 1.447(6) . ? 
N2 C21 1.464(6) . ? 
C3 C4 1.383(7) . ? 
C4 C5 1.376(6) . ? 
C5 C6 1.379(5) . ? 
C6 N14 1.463(4) . ? 
C6 C8 1.531(4) . ? 
C8 C13 1.388(4) . ? 
C8 C9 1.393(4) . ? 
C9 C10 1.398(4) . ? 
C9 N23 1.431(4) . ? 
C10 C11 1.376(5) . ? 
C11 C12 1.370(5) . ? 
C12 C13 1.383(4) . ? 
N14 C15 1.378(4) . ? 
C15 N16 1.339(5) . ? 
C15 C20 1.404(5) . ? 
N16 C17 1.355(5) . ? 
C17 C18 1.367(8) . ? 
C18 C19 1.369(8) . ? 
C19 C20 1.363(6) . ? 
N23 C24 1.331(5) . ? 
N23 C23 1.461(4) . ? 
C24 O24 1.216(5) . ? 
  
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 
C6 C1 C2 119.6(3) . . ? 
C6 C1 C6 120.6(3) . . ? 
C2 C1 C6 119.8(3) . . ? 
C3 C2 C1 118.3(4) . . ? 
C3 C2 N2 123.1(3) . . ? 
C1 C2 N2 118.5(3) . . ? 
C2 N2 C22 115.6(4) . . ? 
C2 N2 C21 113.4(3) . . ? 
C22 N2 C21 112.9(5) . . ? 
C4 C3 C2 121.4(4) . . ? 
C5 C4 C3 119.4(3) . . ? 
C4 C5 C6 120.5(4) . . ? 
C4 C5 Cl1 120.7(3) . . ? 
C6 C5 Cl1 118.8(3) . . ? 
N14 C6 C1 113.4(2) . . ? 
N14 C6 C8 107.5(2) . . ? 
C1 C6 C8 111.6(2) . . ? 
C5 C6 C1 120.8(4) . . ? 
C13 C8 C9 118.3(2) . . ? 
C13 C8 C6 120.4(2) . . ? 
C9 C8 C6 121.2(2) . . ? 
C8 C9 C10 120.6(3) . . ? 
C8 C9 N23 121.2(2) . . ? 
C10 C9 N23 118.2(3) . . ? 
C11 C10 C9 120.2(3) . . ? 
C12 C11 C10 119.2(3) . . ? 
C11 C12 C13 121.5(3) . . ? 
C11 C12 Cl2 119.6(2) . . ? 
C13 C12 Cl2 119.0(3) . . ? 
C12 C13 C8 120.3(3) . . ? 
C15 N14 C6 121.4(3) . . ? 
N16 C15 N14 117.5(3) . . ? 
N16 C15 C20 123.1(3) . . ? 
N14 C15 C20 119.4(3) . . ? 
C15 N16 C17 116.1(4) . . ? 
N16 C17 C18 124.0(5) . . ? 
C17 C18 C19 118.6(4) . . ? 
C20 C19 C18 119.8(5) . . ? 
C19 C20 C15 118.4(5) . . ? 
C24 N23 C9 118.2(3) . . ? 
C24 N23 C23 120.3(3) . . ? 
C9 N23 C23 121.4(3) . . ? 
O24 C24 N23 125.3(4) . . ? 
  
_refine_diff_density_max    0.377 
_refine_diff_density_min   -0.452 
_refine_diff_density_rms    0.046