# Copyright The Royal Society of Chemistry, 1999
# CCDC Number: 186/1373

data_new 
  
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C10 H18 Cl3 N6 P' 
_chemical_formula_weight          359.62 
_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'   0.0033   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' 
 'P'  'P'   0.1023   0.0942 
 '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    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                    9.4314(3) 
_cell_length_b                    11.7824(3) 
_cell_length_c                    14.6793(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  91.9310(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      1630.30(8) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     213(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
  
_exptl_crystal_description        parallelpip 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       no 
_exptl_crystal_density_diffrn     1.465 
_exptl_crystal_density_method     N/A 
_exptl_crystal_F_000              744 
_exptl_absorpt_coefficient_mu     0.659 
_exptl_absorpt_correction_type    SADABS 
_exptl_absorpt_correction_T_min   0.719603 
_exptl_absorpt_correction_T_max   0.948857 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       213(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       'Siemens CCD ' 
_diffrn_measurement_method       '\w oscillation, 0.3 deg' 
_diffrn_standards_number         '50 frames' 
_diffrn_standards_interval_count 'beginning & end' 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         <1 
_diffrn_reflns_number             10014 
_diffrn_reflns_av_R_equivalents   0.0375 
_diffrn_reflns_av_sigmaI/netI     0.0468 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -13 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          2.16 
_diffrn_reflns_theta_max          28.24 
_reflns_number_total              3862 
_reflns_number_observed           2978 
_reflns_observed_criterion        >2sigma(I) 
  
_computing_data_collection        'ASTRO (SIEMENS, V4.033, 1994)' 
_computing_cell_refinement        'SMART (SIEMENS, V4.033, 1994)' 
_computing_data_reduction         'SAINT (SIEMENS, V4.035, 1994)' 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'SHELXTL (SIEMENS, 1994, ver 5.04)' 
_computing_publication_material   'CIFTAB (Sheldrick, 1993)' 
  
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 0 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^)+(0.0514P)^2^+0.1315P] 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     riding 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0009(8) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          3862 
_refine_ls_number_parameters      254 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0591 
_refine_ls_R_factor_obs           0.0391 
_refine_ls_wR_factor_all          0.1017 
_refine_ls_wR_factor_obs          0.0938 
_refine_ls_goodness_of_fit_all    1.027 
_refine_ls_goodness_of_fit_obs    1.089 
_refine_ls_restrained_S_all       1.027 
_refine_ls_restrained_S_obs       1.089 
_refine_ls_shift/esd_max          0.000 
_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 0.24105(6) 0.10205(4) 0.07739(4) 0.0403(2) Uani 1 d . . 
Cl2 Cl -0.06067(5) 0.15645(4) 0.00648(4) 0.0367(2) Uani 1 d . . 
Cl3 Cl 0.41087(8) 0.67421(7) -0.41824(5) 0.0678(2) Uani 1 d . . 
P1 P 0.11745(5) 0.23807(4) 0.04883(3) 0.02688(14) Uani 1 d . . 
N1 N 0.1809(2) 0.30632(13) -0.03284(11) 0.0301(4) Uani 1 d . . 
N2 N 0.1710(2) 0.47701(13) 0.06035(11) 0.0290(4) Uani 1 d . . 
N3 N 0.0893(2) 0.30761(14) 0.13871(11) 0.0315(4) Uani 1 d . . 
N4 N 0.2634(2) 0.47850(13) -0.08250(11) 0.0310(4) Uani 1 d . . 
N5 N 0.4284(2) 0.59395(14) -0.21194(11) 0.0314(4) Uani 1 d . . 
N6 N 0.0900(2) 0.48385(15) 0.20570(11) 0.0344(4) Uani 1 d . . 
C1 C 0.2024(2) 0.4193(2) -0.01562(13) 0.0268(4) Uani 1 d . . 
C2 C 0.1174(2) 0.4211(2) 0.13149(13) 0.0280(4) Uani 1 d . . 
C3 C 0.1168(3) 0.6059(2) 0.2077(2) 0.0446(6) Uani 1 d . . 
H3A H 0.2076(41) 0.6204(28) 0.2285(25) 0.085(11) Uiso 1 d . . 
H3B H 0.0634(39) 0.6502(29) 0.2515(27) 0.096(11) Uiso 1 d . . 
H3C H 0.0841(37) 0.6416(28) 0.1551(26) 0.091(12) Uiso 1 d . . 
C4 C 0.0435(3) 0.4293(2) 0.2895(2) 0.0439(6) Uani 1 d . . 
H4A H -0.0538(49) 0.4091(33) 0.2866(29) 0.121(15) Uiso 1 d . . 
H4B H 0.0589(39) 0.4732(31) 0.3308(25) 0.098(13) Uiso 1 d . . 
H4C H 0.0898(33) 0.3545(27) 0.3005(21) 0.075(9) Uiso 1 d . . 
C5 C 0.2903(3) 0.4282(2) -0.17137(15) 0.0363(5) Uani 1 d . . 
H5A H 0.2100(25) 0.4553(19) -0.2172(16) 0.039(6) Uiso 1 d . . 
H5B H 0.2906(26) 0.3526(22) -0.1652(18) 0.047(7) Uiso 1 d . . 
C6 C 0.4307(2) 0.4705(2) -0.2057(2) 0.0348(5) Uani 1 d . . 
H6A H 0.5081(28) 0.4433(20) -0.1650(17) 0.049(7) Uiso 1 d . . 
H6B H 0.4413(24) 0.4368(18) -0.2668(17) 0.040(6) Uiso 1 d . . 
C7 C 0.4147(3) 0.6404(2) -0.1199(2) 0.0376(5) Uani 1 d . . 
H7A H 0.4131(22) 0.7280(19) -0.1247(15) 0.033(6) Uiso 1 d . . 
H7B H 0.4957(31) 0.6148(23) -0.0805(21) 0.062(8) Uiso 1 d . . 
C8 C 0.2756(3) 0.6025(2) -0.0800(2) 0.0350(5) Uani 1 d . . 
H8A H 0.2678(25) 0.6269(20) -0.0217(18) 0.043(7) Uiso 1 d . . 
H8B H 0.1947(29) 0.6387(21) -0.1159(19) 0.054(7) Uiso 1 d . . 
C9 C 0.5536(3) 0.6397(2) -0.2553(2) 0.0417(5) Uani 1 d . . 
H9A H 0.6453(28) 0.6035(21) -0.2224(18) 0.053(7) Uiso 1 d . . 
H9B H 0.5479(24) 0.7252(20) -0.2479(16) 0.039(6) Uiso 1 d . . 
C10 C 0.5589(3) 0.6154(2) -0.3559(2) 0.0412(5) Uani 1 d . . 
H10A H 0.6454(29) 0.6522(21) -0.3774(19) 0.058(8) Uiso 1 d . . 
H10B H 0.5574(23) 0.5347(19) -0.3728(15) 0.033(6) Uiso 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 0.0431(3) 0.0381(3) 0.0400(3) 0.0079(2) 0.0065(2) 0.0104(2) 
Cl2 0.0364(3) 0.0351(3) 0.0389(3) -0.0050(2) 0.0041(2) -0.0055(2) 
Cl3 0.0640(4) 0.0845(5) 0.0540(4) 0.0295(4) -0.0092(3) -0.0075(4) 
P1 0.0315(3) 0.0270(2) 0.0225(3) 0.0001(2) 0.0071(2) -0.0003(2) 
N1 0.0414(10) 0.0255(8) 0.0242(8) -0.0019(7) 0.0114(7) -0.0017(7) 
N2 0.0333(9) 0.0305(8) 0.0235(8) -0.0015(7) 0.0071(7) 0.0014(7) 
N3 0.0397(10) 0.0316(8) 0.0236(8) -0.0011(7) 0.0092(7) -0.0031(7) 
N4 0.0433(10) 0.0258(8) 0.0247(8) -0.0022(7) 0.0139(7) -0.0017(7) 
N5 0.0319(9) 0.0344(9) 0.0283(9) 0.0036(7) 0.0070(7) -0.0046(7) 
N6 0.0431(10) 0.0370(9) 0.0237(8) -0.0050(7) 0.0093(7) 0.0026(8) 
C1 0.0270(10) 0.0290(9) 0.0247(9) -0.0005(8) 0.0048(8) 0.0018(7) 
C2 0.0256(10) 0.0353(10) 0.0234(9) -0.0036(8) 0.0058(8) 0.0016(8) 
C3 0.061(2) 0.0367(12) 0.0366(13) -0.0096(11) 0.0110(12) 0.0016(11) 
C4 0.061(2) 0.0500(14) 0.0221(11) -0.0006(10) 0.0153(11) 0.0090(13) 
C5 0.0530(14) 0.0307(11) 0.0263(11) -0.0028(9) 0.0175(10) -0.0066(10) 
C6 0.0395(12) 0.0372(11) 0.0283(11) 0.0012(9) 0.0096(9) 0.0043(9) 
C7 0.0456(13) 0.0343(11) 0.0335(12) -0.0026(9) 0.0093(10) -0.0073(10) 
C8 0.0456(13) 0.0266(10) 0.0335(12) -0.0015(9) 0.0143(10) 0.0001(9) 
C9 0.0345(12) 0.0552(14) 0.0360(12) 0.0023(11) 0.0080(10) -0.0120(10) 
C10 0.0388(13) 0.0487(14) 0.0368(12) 0.0081(11) 0.0099(10) -0.0062(10) 
  
_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 P1 2.0175(7) . ? 
Cl2 P1 2.0156(7) . ? 
Cl3 C10 1.783(3) . ? 
P1 N1 1.578(2) . ? 
P1 N3 1.583(2) . ? 
N1 C1 1.368(2) . ? 
N2 C2 1.347(2) . ? 
N2 C1 1.348(2) . ? 
N3 C2 1.368(3) . ? 
N4 C1 1.349(2) . ? 
N4 C5 1.463(2) . ? 
N4 C8 1.466(3) . ? 
N5 C6 1.457(3) . ? 
N5 C9 1.464(3) . ? 
N5 C7 1.467(3) . ? 
N6 C2 1.349(2) . ? 
N6 C3 1.461(3) . ? 
N6 C4 1.467(3) . ? 
C3 H3A 0.92(4) . ? 
C3 H3B 0.98(4) . ? 
C3 H3C 0.92(4) . ? 
C4 H4A 0.95(5) . ? 
C4 H4B 0.81(4) . ? 
C4 H4C 0.99(3) . ? 
C5 C6 1.517(3) . ? 
C5 H5A 1.05(2) . ? 
C5 H5B 0.90(2) . ? 
C6 H6A 0.98(3) . ? 
C6 H6B 0.99(2) . ? 
C7 C8 1.521(3) . ? 
C7 H7A 1.03(2) . ? 
C7 H7B 0.99(3) . ? 
C8 H8A 0.91(3) . ? 
C8 H8B 1.01(3) . ? 
C9 C10 1.508(3) . ? 
C9 H9A 1.07(3) . ? 
C9 H9B 1.01(2) . ? 
C10 H10A 0.98(3) . ? 
C10 H10B 0.98(2) . ? 
  
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 
N1 P1 N3 116.61(9) . . ? 
N1 P1 Cl2 110.02(7) . . ? 
N3 P1 Cl2 110.03(7) . . ? 
N1 P1 Cl1 109.35(7) . . ? 
N3 P1 Cl1 110.48(7) . . ? 
Cl2 P1 Cl1 98.91(3) . . ? 
C1 N1 P1 114.38(13) . . ? 
C2 N2 C1 119.5(2) . . ? 
C2 N3 P1 113.76(13) . . ? 
C1 N4 C5 122.0(2) . . ? 
C1 N4 C8 122.2(2) . . ? 
C5 N4 C8 114.2(2) . . ? 
C6 N5 C9 112.6(2) . . ? 
C6 N5 C7 108.5(2) . . ? 
C9 N5 C7 111.1(2) . . ? 
C2 N6 C3 121.2(2) . . ? 
C2 N6 C4 120.5(2) . . ? 
C3 N6 C4 118.1(2) . . ? 
N2 C1 N4 116.9(2) . . ? 
N2 C1 N1 127.5(2) . . ? 
N4 C1 N1 115.6(2) . . ? 
N2 C2 N6 116.4(2) . . ? 
N2 C2 N3 128.1(2) . . ? 
N6 C2 N3 115.5(2) . . ? 
N6 C3 H3A 110.5(22) . . ? 
N6 C3 H3B 116.4(20) . . ? 
H3A C3 H3B 100.2(29) . . ? 
N6 C3 H3C 112.3(21) . . ? 
H3A C3 H3C 118.6(30) . . ? 
H3B C3 H3C 98.1(28) . . ? 
N6 C4 H4A 112.9(26) . . ? 
N6 C4 H4B 107.3(25) . . ? 
H4A C4 H4B 110.1(34) . . ? 
N6 C4 H4C 112.5(17) . . ? 
H4A C4 H4C 101.8(29) . . ? 
H4B C4 H4C 112.3(31) . . ? 
N4 C5 C6 110.0(2) . . ? 
N4 C5 H5A 107.8(12) . . ? 
C6 C5 H5A 107.9(12) . . ? 
N4 C5 H5B 108.2(17) . . ? 
C6 C5 H5B 111.1(16) . . ? 
H5A C5 H5B 111.7(21) . . ? 
N5 C6 C5 109.7(2) . . ? 
N5 C6 H6A 111.9(14) . . ? 
C5 C6 H6A 109.3(14) . . ? 
N5 C6 H6B 110.3(13) . . ? 
C5 C6 H6B 106.6(13) . . ? 
H6A C6 H6B 108.9(19) . . ? 
N5 C7 C8 110.4(2) . . ? 
N5 C7 H7A 108.1(12) . . ? 
C8 C7 H7A 108.0(12) . . ? 
N5 C7 H7B 109.5(16) . . ? 
C8 C7 H7B 110.2(16) . . ? 
H7A C7 H7B 110.7(20) . . ? 
N4 C8 C7 110.6(2) . . ? 
N4 C8 H8A 109.3(15) . . ? 
C7 C8 H8A 111.6(16) . . ? 
N4 C8 H8B 110.6(14) . . ? 
C7 C8 H8B 108.8(15) . . ? 
H8A C8 H8B 106.0(21) . . ? 
N5 C9 C10 114.2(2) . . ? 
N5 C9 H9A 108.1(14) . . ? 
C10 C9 H9A 108.3(14) . . ? 
N5 C9 H9B 105.8(13) . . ? 
C10 C9 H9B 107.3(14) . . ? 
H9A C9 H9B 113.3(19) . . ? 
C9 C10 Cl3 112.2(2) . . ? 
C9 C10 H10A 106.5(16) . . ? 
Cl3 C10 H10A 107.9(16) . . ? 
C9 C10 H10B 115.5(13) . . ? 
Cl3 C10 H10B 104.0(13) . . ? 
H10A C10 H10B 110.5(19) . . ? 
  
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 
 N3 P1 N1 C1 -0.7(2) . . . . ? 
 Cl2 P1 N1 C1 125.45(14) . . . . ? 
 Cl1 P1 N1 C1 -126.94(14) . . . . ? 
 N1 P1 N3 C2 3.4(2) . . . . ? 
 Cl2 P1 N3 C2 -122.82(14) . . . . ? 
 Cl1 P1 N3 C2 129.00(14) . . . . ? 
 C2 N2 C1 N4 -176.3(2) . . . . ? 
 C2 N2 C1 N1 3.0(3) . . . . ? 
 C5 N4 C1 N2 -174.1(2) . . . . ? 
 C8 N4 C1 N2 -9.2(3) . . . . ? 
 C5 N4 C1 N1 6.5(3) . . . . ? 
 C8 N4 C1 N1 171.4(2) . . . . ? 
 P1 N1 C1 N2 -2.6(3) . . . . ? 
 P1 N1 C1 N4 176.73(14) . . . . ? 
 C1 N2 C2 N6 179.2(2) . . . . ? 
 C1 N2 C2 N3 0.5(3) . . . . ? 
 C3 N6 C2 N2 0.3(3) . . . . ? 
 C4 N6 C2 N2 -174.5(2) . . . . ? 
 C3 N6 C2 N3 179.2(2) . . . . ? 
 C4 N6 C2 N3 4.4(3) . . . . ? 
 P1 N3 C2 N2 -3.4(3) . . . . ? 
 P1 N3 C2 N6 177.79(14) . . . . ? 
 C1 N4 C5 C6 -142.1(2) . . . . ? 
 C8 N4 C5 C6 51.9(3) . . . . ? 
 C9 N5 C6 C5 -172.9(2) . . . . ? 
 C7 N5 C6 C5 63.7(2) . . . . ? 
 N4 C5 C6 N5 -58.1(3) . . . . ? 
 C6 N5 C7 C8 -62.1(2) . . . . ? 
 C9 N5 C7 C8 173.6(2) . . . . ? 
 C1 N4 C8 C7 143.7(2) . . . . ? 
 C5 N4 C8 C7 -50.3(3) . . . . ? 
 N5 C7 C8 N4 54.6(3) . . . . ? 
 C6 N5 C9 C10 70.1(3) . . . . ? 
 C7 N5 C9 C10 -168.0(2) . . . . ? 
 N5 C9 C10 Cl3 60.4(3) . . . . ? 
  
_refine_diff_density_max    0.314 
_refine_diff_density_min   -0.360 
_refine_diff_density_rms    0.058