# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_try _database_code_depnum_ccdc_archive 'CCDC 895219' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H20 Cl2 N4 Ni' _chemical_formula_weight 325.91 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.0672(11) _cell_length_b 13.6398(12) _cell_length_c 12.880(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.756(13) _cell_angle_gamma 90.00 _cell_volume 1392.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 12.50 _exptl_crystal_description ? _exptl_crystal_colour orange _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.762 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4179 _exptl_absorpt_correction_T_max 0.7196 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6878 _diffrn_reflns_av_R_equivalents 0.0664 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 26.36 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 2837 _reflns_number_gt 2486 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.3000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2837 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.514 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.072 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 Ni Ni 0.05483(3) 0.209968(17) 0.282926(19) 0.02086(11) Uani 1 1 d . . . Cl1 Cl -0.14569(8) 0.09949(4) 0.22873(4) 0.03228(15) Uani 1 1 d . . . Cl2 Cl 0.04583(8) 0.27275(4) 0.12357(4) 0.03163(15) Uani 1 1 d . . . C1 C 0.2079(3) 0.30815(16) 0.33614(16) 0.0259(5) Uani 1 1 d . . . C2 C 0.4579(4) 0.39063(18) 0.4038(2) 0.0440(7) Uani 1 1 d . . . H2A H 0.5250 0.4222 0.3560 0.053 Uiso 1 1 calc R . . H2B H 0.5322 0.3766 0.4724 0.053 Uiso 1 1 calc R . . C3 C 0.3090(4) 0.45415(19) 0.41793(19) 0.0460(7) Uani 1 1 d . . . H3A H 0.3052 0.4632 0.4937 0.055 Uiso 1 1 calc R . . H3B H 0.3142 0.5192 0.3846 0.055 Uiso 1 1 calc R . . C4 C 0.4744(4) 0.2187(2) 0.3345(2) 0.0386(6) Uani 1 1 d . . . H4A H 0.3993 0.1660 0.3025 0.058 Uiso 1 1 calc R . . H4B H 0.5438 0.1952 0.4005 0.058 Uiso 1 1 calc R . . H4C H 0.5477 0.2387 0.2856 0.058 Uiso 1 1 calc R . . C5 C -0.0011(4) 0.44162(17) 0.33930(19) 0.0404(6) Uani 1 1 d . . . H5A H -0.0821 0.3931 0.3039 0.061 Uiso 1 1 calc R . . H5B H 0.0020 0.4978 0.2923 0.061 Uiso 1 1 calc R . . H5C H -0.0357 0.4636 0.4045 0.061 Uiso 1 1 calc R . . C6 C 0.0991(3) 0.15445(15) 0.41882(16) 0.0249(4) Uani 1 1 d . . . C7 C 0.2193(4) 0.04899(19) 0.55489(18) 0.0400(6) Uani 1 1 d . . . H7A H 0.3404 0.0465 0.5878 0.048 Uiso 1 1 calc R . . H7B H 0.1667 -0.0152 0.5645 0.048 Uiso 1 1 calc R . . C8 C 0.1296(4) 0.1318(2) 0.60071(18) 0.0405(6) Uani 1 1 d . . . H8A H 0.0452 0.1062 0.6406 0.049 Uiso 1 1 calc R . . H8B H 0.2107 0.1742 0.6477 0.049 Uiso 1 1 calc R . . C9 C 0.2596(4) 0.01182(18) 0.3699(2) 0.0416(6) Uani 1 1 d . . . H9A H 0.2326 0.0397 0.2986 0.062 Uiso 1 1 calc R . . H9B H 0.2070 -0.0529 0.3703 0.062 Uiso 1 1 calc R . . H9C H 0.3822 0.0054 0.3912 0.062 Uiso 1 1 calc R . . C10 C -0.0520(4) 0.2704(2) 0.5162(2) 0.0412(6) Uani 1 1 d . . . H10A H -0.0976 0.2969 0.4459 0.062 Uiso 1 1 calc R . . H10B H 0.0185 0.3201 0.5581 0.062 Uiso 1 1 calc R . . H10C H -0.1452 0.2525 0.5516 0.062 Uiso 1 1 calc R . . N1 N 0.3752(3) 0.30116(15) 0.35649(16) 0.0333(5) Uani 1 1 d . . . N2 N 0.1637(3) 0.39800(14) 0.36443(15) 0.0355(5) Uani 1 1 d . . . N3 N 0.1963(3) 0.07550(14) 0.44280(14) 0.0326(4) Uani 1 1 d . . . N4 N 0.0480(3) 0.18502(15) 0.50579(14) 0.0311(4) Uani 1 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 Ni 0.02401(17) 0.01931(15) 0.01876(16) -0.00160(9) 0.00269(12) -0.00144(11) Cl1 0.0341(3) 0.0291(3) 0.0316(3) -0.0016(2) 0.0008(2) -0.0092(2) Cl2 0.0402(3) 0.0330(3) 0.0214(3) 0.00146(19) 0.0051(2) -0.0041(2) C1 0.0344(12) 0.0262(10) 0.0162(9) 0.0014(7) 0.0027(9) -0.0044(10) C2 0.0482(16) 0.0386(13) 0.0376(13) 0.0086(10) -0.0116(12) -0.0224(13) C3 0.072(2) 0.0337(12) 0.0277(12) -0.0040(9) -0.0026(13) -0.0207(14) C4 0.0304(13) 0.0506(15) 0.0347(12) 0.0005(10) 0.0054(11) -0.0007(12) C5 0.0587(17) 0.0274(11) 0.0341(11) -0.0023(9) 0.0063(12) 0.0079(13) C6 0.0229(11) 0.0246(10) 0.0258(10) -0.0008(8) 0.0013(9) -0.0056(9) C7 0.0412(15) 0.0427(13) 0.0318(12) 0.0155(10) -0.0045(11) -0.0066(12) C8 0.0378(14) 0.0576(16) 0.0251(11) 0.0091(10) 0.0031(10) -0.0071(13) C9 0.0373(14) 0.0328(12) 0.0541(15) 0.0009(11) 0.0072(12) 0.0083(12) C10 0.0434(16) 0.0481(14) 0.0360(13) -0.0052(11) 0.0176(12) 0.0029(13) N1 0.0331(11) 0.0356(10) 0.0282(10) -0.0008(8) -0.0020(9) -0.0119(10) N2 0.0496(13) 0.0245(9) 0.0287(10) -0.0059(7) -0.0020(9) -0.0061(10) N3 0.0356(11) 0.0304(9) 0.0310(10) 0.0076(8) 0.0042(9) 0.0024(9) N4 0.0339(11) 0.0372(10) 0.0225(9) 0.0007(8) 0.0058(8) -0.0016(9) _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 Ni C1 1.863(2) . ? Ni C6 1.879(2) . ? Ni Cl2 2.2127(7) . ? Ni Cl1 2.2256(6) . ? C1 N1 1.329(3) . ? C1 N2 1.345(3) . ? C2 N1 1.467(3) . ? C2 C3 1.519(4) . ? C3 N2 1.461(3) . ? C4 N1 1.439(3) . ? C5 N2 1.437(4) . ? C6 N4 1.331(3) . ? C6 N3 1.334(3) . ? C7 N3 1.466(3) . ? C7 C8 1.519(4) . ? C8 N4 1.468(3) . ? C9 N3 1.441(3) . ? C10 N4 1.438(3) . ? 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 C1 Ni C6 87.09(9) . . ? C1 Ni Cl2 88.16(6) . . ? C6 Ni Cl2 170.96(7) . . ? C1 Ni Cl1 174.24(7) . . ? C6 Ni Cl1 91.15(7) . . ? Cl2 Ni Cl1 94.30(2) . . ? N1 C1 N2 108.8(2) . . ? N1 C1 Ni 126.84(18) . . ? N2 C1 Ni 124.3(2) . . ? N1 C2 C3 102.5(2) . . ? N2 C3 C2 103.1(2) . . ? N4 C6 N3 108.62(18) . . ? N4 C6 Ni 128.51(17) . . ? N3 C6 Ni 122.84(16) . . ? N3 C7 C8 102.55(19) . . ? N4 C8 C7 102.49(19) . . ? C1 N1 C4 126.8(2) . . ? C1 N1 C2 112.9(2) . . ? C4 N1 C2 120.3(2) . . ? C1 N2 C5 126.6(2) . . ? C1 N2 C3 112.0(2) . . ? C5 N2 C3 121.1(2) . . ? C6 N3 C9 126.89(19) . . ? C6 N3 C7 112.82(19) . . ? C9 N3 C7 119.9(2) . . ? C6 N4 C10 126.9(2) . . ? C6 N4 C8 112.6(2) . . ? C10 N4 C8 119.7(2) . . ? data_try2 _database_code_depnum_ccdc_archive 'CCDC 895220' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H13 Cl2 N2 P' _chemical_formula_weight 215.05 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.768(2) _cell_length_b 12.985(3) _cell_length_c 19.423(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1959.2(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 12.52 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.90 _exptl_crystal_size_min 0.80 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.769 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5137 _exptl_absorpt_correction_T_max 0.5784 _exptl_absorpt_process_details SADABS _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 'Bruker APEX-II CCD' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5553 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 2243 _reflns_number_gt 2033 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.8000P] 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 calcall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2243 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0845 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.373 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.065 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 0.4468(2) 0.08118(11) 0.38122(7) 0.0168(3) Uani 1 1 d . . . C2 C 0.7244(2) 0.04451(13) 0.41763(10) 0.0249(4) Uani 1 1 d . . . H22 H 0.793(3) 0.0090(19) 0.3841(13) 0.037(6) Uiso 1 1 d . . . H21 H 0.763(3) 0.0291(18) 0.4612(13) 0.035(6) Uiso 1 1 d . . . C3 C 0.7074(2) 0.15971(13) 0.40424(9) 0.0239(3) Uani 1 1 d . . . H32 H 0.720(3) 0.2031(17) 0.4437(12) 0.032(6) Uiso 1 1 d . . . H31 H 0.790(3) 0.1869(17) 0.3691(12) 0.034(6) Uiso 1 1 d . . . C4 C 0.5082(3) -0.10127(13) 0.41444(11) 0.0303(4) Uani 1 1 d . . . H43 H 0.547(3) -0.1379(18) 0.3740(13) 0.040(6) Uiso 1 1 d . . . H42 H 0.390(3) -0.1135(19) 0.4177(12) 0.035(6) Uiso 1 1 d . . . H41 H 0.561(3) -0.1257(19) 0.4547(13) 0.042(7) Uiso 1 1 d . . . C5 C 0.4650(3) 0.27374(12) 0.36534(10) 0.0261(3) Uani 1 1 d . . . H53 H 0.506(4) 0.3026(19) 0.3245(14) 0.048(7) Uiso 1 1 d . . . H52 H 0.505(4) 0.317(2) 0.3977(14) 0.049(7) Uiso 1 1 d . . . H51 H 0.349(4) 0.274(2) 0.3643(13) 0.042(7) Uiso 1 1 d . . . C6 C 0.1589(2) 0.14949(14) 0.29417(9) 0.0260(4) Uani 1 1 d . . . H63 H 0.251(3) 0.1763(19) 0.2675(13) 0.041(6) Uiso 1 1 d . . . H62 H 0.108(3) 0.2034(19) 0.3168(12) 0.036(6) Uiso 1 1 d . . . H61 H 0.076(3) 0.1147(19) 0.2620(12) 0.038(6) Uiso 1 1 d . . . N1 N 0.54568(18) 0.00825(10) 0.40863(7) 0.0215(3) Uani 1 1 d . . . N2 N 0.53071(17) 0.16979(10) 0.37684(7) 0.0196(3) Uani 1 1 d . . . P1 P 0.22206(5) 0.04656(3) 0.35446(2) 0.01976(13) Uani 1 1 d . . . Cl1 Cl 0.13620(5) 0.15180(3) 0.45461(2) 0.02416(12) Uani 1 1 d . . . Cl2 Cl 0.33885(6) -0.04307(3) 0.26399(2) 0.02942(14) Uani 1 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 C1 0.0173(7) 0.0172(6) 0.0158(6) -0.0012(5) 0.0006(5) -0.0002(6) C2 0.0180(8) 0.0259(8) 0.0309(9) -0.0002(6) -0.0042(7) 0.0013(6) C3 0.0200(8) 0.0243(7) 0.0274(8) -0.0014(6) -0.0029(6) -0.0032(6) C4 0.0337(10) 0.0158(7) 0.0413(10) 0.0032(7) -0.0100(8) 0.0011(7) C5 0.0292(9) 0.0154(7) 0.0336(9) 0.0025(6) -0.0027(7) -0.0014(6) C6 0.0271(9) 0.0292(8) 0.0219(8) 0.0006(6) -0.0058(6) 0.0032(7) N1 0.0210(7) 0.0158(6) 0.0278(7) 0.0001(5) -0.0044(5) -0.0002(5) N2 0.0184(6) 0.0171(6) 0.0232(6) 0.0016(5) -0.0006(5) -0.0010(5) P1 0.0176(2) 0.0188(2) 0.0229(2) -0.00045(14) -0.00206(14) -0.00171(14) Cl1 0.0245(2) 0.0266(2) 0.0215(2) -0.00178(14) 0.00085(14) 0.00424(15) Cl2 0.0305(3) 0.0305(2) 0.0272(2) -0.01058(15) 0.00073(16) 0.00017(16) _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 N2 1.3250(19) . ? C1 N1 1.330(2) . ? C1 P1 1.8764(16) . ? C2 N1 1.476(2) . ? C2 C3 1.524(2) . ? C3 N2 1.478(2) . ? C4 N1 1.456(2) . ? C5 N2 1.460(2) . ? C6 P1 1.8435(18) . ? P1 Cl2 2.2947(7) . ? P1 Cl1 2.4691(7) . ? 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 N2 C1 N1 111.11(14) . . ? N2 C1 P1 130.38(11) . . ? N1 C1 P1 118.51(11) . . ? N1 C2 C3 102.22(13) . . ? N2 C3 C2 103.21(13) . . ? C1 N1 C4 127.64(14) . . ? C1 N1 C2 111.29(13) . . ? C4 N1 C2 119.38(14) . . ? C1 N2 C5 129.84(14) . . ? C1 N2 C3 110.89(13) . . ? C5 N2 C3 117.49(13) . . ? C6 P1 C1 104.47(7) . . ? C6 P1 Cl2 89.23(6) . . ? C1 P1 Cl2 88.04(5) . . ? C6 P1 Cl1 91.56(6) . . ? C1 P1 Cl1 84.29(5) . . ? Cl2 P1 Cl1 172.24(2) . . ? data_try3 _database_code_depnum_ccdc_archive 'CCDC 895221' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H15 Cl2 N2 P' _chemical_formula_weight 277.12 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 C2/c 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' '-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 19.240(3) _cell_length_b 11.531(3) _cell_length_c 15.038(3) _cell_angle_alpha 90.00 _cell_angle_beta 128.66(3) _cell_angle_gamma 90.00 _cell_volume 2605.4(9) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 51 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 12.51 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 1.0 _exptl_crystal_size_mid 0.9 _exptl_crystal_size_min 0.7 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.596 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6638 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 2974 _reflns_number_gt 2680 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.2000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2974 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.363 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.049 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 0.13809(8) 0.69851(12) 0.08585(11) 0.0218(3) Uani 1 1 d . . . C2 C 0.04179(11) 0.77552(18) -0.09504(13) 0.0372(4) Uani 1 1 d . . . H22 H -0.0194(16) 0.736(2) -0.153(2) 0.053(6) Uiso 1 1 d . . . H21 H 0.0619(14) 0.8132(18) -0.1338(17) 0.040(5) Uiso 1 1 d . . . C3 C 0.04533(11) 0.85550(15) -0.01203(15) 0.0333(3) Uani 1 1 d . . . H32 H -0.0143(14) 0.8618(18) -0.0337(17) 0.037(5) Uiso 1 1 d . . . H31 H 0.0691(15) 0.934(2) -0.0039(19) 0.050(6) Uiso 1 1 d . . . C4 C 0.12343(11) 0.59351(16) -0.07096(13) 0.0315(3) Uani 1 1 d . . . H43 H 0.0631(14) 0.5537(19) -0.1337(18) 0.045(6) Uiso 1 1 d . . . H42 H 0.1642(15) 0.5383(19) -0.0154(19) 0.042(5) Uiso 1 1 d . . . H41 H 0.1468(14) 0.6307(19) -0.1045(17) 0.041(5) Uiso 1 1 d . . . C5 C 0.11516(11) 0.83602(16) 0.19551(14) 0.0322(3) Uani 1 1 d . . . H53 H 0.0568(16) 0.850(2) 0.1704(19) 0.047(6) Uiso 1 1 d . . . H52 H 0.1369(14) 0.775(2) 0.2479(19) 0.043(6) Uiso 1 1 d . . . H51 H 0.146(2) 0.901(3) 0.215(2) 0.075(8) Uiso 1 1 d . . . C6 C 0.27642(9) 0.65417(13) 0.33286(11) 0.0243(3) Uani 1 1 d . . . C7 C 0.28671(10) 0.59141(15) 0.41996(13) 0.0306(3) Uani 1 1 d . . . H71 H 0.2559(13) 0.5199(19) 0.3989(16) 0.036(5) Uiso 1 1 d . . . C8 C 0.34026(12) 0.63407(17) 0.53091(13) 0.0375(4) Uani 1 1 d . . . H81 H 0.3519(15) 0.587(2) 0.5892(19) 0.048(6) Uiso 1 1 d . . . C9 C 0.38384(11) 0.73910(17) 0.55564(13) 0.0388(4) Uani 1 1 d . . . H91 H 0.4210(16) 0.769(2) 0.631(2) 0.056(6) Uiso 1 1 d . . . C10 C 0.37531(10) 0.80129(15) 0.47007(14) 0.0335(4) Uani 1 1 d . . . H101 H 0.4094(14) 0.8685(19) 0.4869(17) 0.038(5) Uiso 1 1 d . . . C11 C 0.32194(9) 0.75894(13) 0.35910(12) 0.0276(3) Uani 1 1 d . . . H111 H 0.3158(13) 0.8034(18) 0.2978(17) 0.035(5) Uiso 1 1 d . . . N1 N 0.10445(8) 0.68313(12) -0.02151(10) 0.0266(3) Uani 1 1 d . . . N2 N 0.10787(8) 0.79578(12) 0.09829(11) 0.0281(3) Uani 1 1 d . . . P1 P 0.21125(2) 0.58291(3) 0.19201(3) 0.02316(13) Uani 1 1 d . . . Cl1 Cl 0.32093(2) 0.64158(3) 0.17114(3) 0.03140(13) Uani 1 1 d . . . Cl2 Cl 0.09147(2) 0.54132(4) 0.18859(3) 0.03276(13) Uani 1 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 C1 0.0170(6) 0.0260(7) 0.0224(6) 0.0003(5) 0.0123(5) -0.0031(5) C2 0.0279(7) 0.0558(11) 0.0298(7) 0.0151(7) 0.0190(6) 0.0112(7) C3 0.0252(7) 0.0316(8) 0.0406(8) 0.0114(7) 0.0193(7) 0.0051(6) C4 0.0314(8) 0.0407(9) 0.0267(7) -0.0058(6) 0.0202(6) -0.0061(7) C5 0.0279(8) 0.0348(9) 0.0355(8) -0.0080(7) 0.0207(7) 0.0005(6) C6 0.0202(6) 0.0286(7) 0.0212(6) 0.0013(5) 0.0114(5) 0.0024(5) C7 0.0277(7) 0.0342(8) 0.0267(7) 0.0044(6) 0.0155(6) 0.0022(6) C8 0.0376(8) 0.0479(10) 0.0254(7) 0.0055(7) 0.0189(7) 0.0072(7) C9 0.0304(8) 0.0491(10) 0.0247(7) -0.0060(7) 0.0112(6) 0.0061(7) C10 0.0258(7) 0.0324(8) 0.0334(8) -0.0072(6) 0.0141(6) 0.0009(6) C11 0.0241(7) 0.0271(7) 0.0272(7) 0.0005(6) 0.0139(6) 0.0014(5) N1 0.0234(6) 0.0345(7) 0.0211(5) 0.0018(5) 0.0134(5) -0.0003(5) N2 0.0256(6) 0.0298(7) 0.0294(6) 0.0030(5) 0.0175(5) 0.0044(5) P1 0.0216(2) 0.0228(2) 0.02243(19) 0.00022(13) 0.01243(16) -0.00046(12) Cl1 0.0246(2) 0.0398(2) 0.0344(2) -0.00372(15) 0.02070(17) -0.00583(14) Cl2 0.0238(2) 0.0419(3) 0.0328(2) 0.00550(14) 0.01776(17) -0.00531(14) _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 N1 1.3234(18) . ? C1 N2 1.3293(19) . ? C1 P1 1.8707(15) . ? C2 N1 1.465(2) . ? C2 C3 1.519(3) . ? C3 N2 1.477(2) . ? C4 N1 1.447(2) . ? C5 N2 1.455(2) . ? C6 C11 1.397(2) . ? C6 C7 1.398(2) . ? C6 P1 1.8482(15) . ? C7 C8 1.393(2) . ? C8 C9 1.385(3) . ? C9 C10 1.390(3) . ? C10 C11 1.392(2) . ? P1 Cl1 2.4161(6) . ? P1 Cl2 2.3227(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 N1 C1 N2 111.17(13) . . ? N1 C1 P1 118.66(11) . . ? N2 C1 P1 130.03(11) . . ? N1 C2 C3 103.18(12) . . ? N2 C3 C2 103.12(13) . . ? C11 C6 C7 119.10(13) . . ? C11 C6 P1 124.41(11) . . ? C7 C6 P1 116.18(12) . . ? C8 C7 C6 120.36(15) . . ? C7 C8 C9 120.08(16) . . ? C10 C9 C8 120.05(15) . . ? C9 C10 C11 120.06(16) . . ? C6 C11 C10 120.34(14) . . ? C1 N1 C4 129.39(13) . . ? C1 N1 C2 111.60(13) . . ? C4 N1 C2 118.97(13) . . ? C1 N2 C5 129.38(13) . . ? C1 N2 C3 110.88(13) . . ? C5 N2 C3 118.67(13) . . ? C6 P1 C1 105.75(7) . . ? C6 P1 Cl1 90.12(5) . . ? C1 P1 Cl1 86.69(4) . . ? C6 P1 Cl2 94.05(5) . . ? C1 P1 Cl2 85.47(5) . . ? Cl2 P1 Cl1 171.88(2) . . ? data_try4 _database_code_depnum_ccdc_archive 'CCDC 895222' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H10 Cl3 N2 P' _chemical_formula_weight 235.47 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' Cl Cl 0.1484 0.1585 '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' _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 11.4381(10) _cell_length_b 7.7170(7) _cell_length_c 12.9790(11) _cell_angle_alpha 90.00 _cell_angle_beta 122.697(6) _cell_angle_gamma 90.00 _cell_volume 964.09(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9238 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 30.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 1.057 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5788 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 53367 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 30.50 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 2934 _reflns_number_gt 2730 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.4000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2934 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.426 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.100 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 0.25155(16) 0.5406(2) 0.47236(13) 0.0129(3) Uani 1 1 d . . . C2 C 0.3021(2) 0.2730(2) 0.56623(16) 0.0197(3) Uani 1 1 d . . . H22 H 0.231(3) 0.185(4) 0.555(3) 0.038(8) Uiso 1 1 d . . . H21 H 0.386(3) 0.257(4) 0.646(3) 0.041(8) Uiso 1 1 d . . . C3 C 0.33822(19) 0.2709(2) 0.46916(16) 0.0182(3) Uani 1 1 d . . . H32 H 0.279(3) 0.190(3) 0.407(2) 0.025(6) Uiso 1 1 d . . . H31 H 0.427(3) 0.261(4) 0.498(3) 0.035(7) Uiso 1 1 d . . . C4 C 0.2244(2) 0.5071(3) 0.65161(19) 0.0249(4) Uani 1 1 d . . . H43 H 0.235(3) 0.615(5) 0.666(3) 0.045(8) Uiso 1 1 d . . . H42 H 0.279(4) 0.451(4) 0.716(3) 0.049(9) Uiso 1 1 d . . . H41 H 0.133(4) 0.485(5) 0.629(3) 0.062(10) Uiso 1 1 d . . . C5 C 0.3177(2) 0.4986(3) 0.31937(17) 0.0231(4) Uani 1 1 d . . . H53 H 0.241(3) 0.460(4) 0.248(3) 0.029(7) Uiso 1 1 d . . . H52 H 0.308(3) 0.616(4) 0.304(3) 0.041(8) Uiso 1 1 d . . . H51 H 0.418(3) 0.446(4) 0.341(3) 0.040(8) Uiso 1 1 d . . . N1 N 0.24495(16) 0.44915(18) 0.55540(13) 0.0166(3) Uani 1 1 d . . . N2 N 0.30884(15) 0.45057(18) 0.42340(13) 0.0161(3) Uani 1 1 d . . . P1 P 0.19325(5) 0.76710(5) 0.41380(4) 0.01470(10) Uani 1 1 d . . . Cl1 Cl 0.01136(5) 0.65299(6) 0.24471(4) 0.02363(11) Uani 1 1 d . . . Cl2 Cl 0.40750(4) 0.84429(5) 0.61180(4) 0.02088(10) Uani 1 1 d . . . Cl3 Cl 0.07475(5) 0.83336(6) 0.48294(4) 0.02149(10) Uani 1 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 C1 0.0167(7) 0.0105(6) 0.0116(6) -0.0003(5) 0.0076(5) 0.0011(5) C2 0.0275(9) 0.0112(7) 0.0195(7) 0.0032(6) 0.0122(7) 0.0037(6) C3 0.0211(8) 0.0119(7) 0.0210(7) -0.0003(6) 0.0112(6) 0.0040(6) C4 0.0415(11) 0.0217(9) 0.0235(8) 0.0040(7) 0.0255(9) 0.0054(8) C5 0.0341(10) 0.0243(9) 0.0191(8) 0.0044(7) 0.0196(8) 0.0096(7) N1 0.0254(7) 0.0122(6) 0.0163(6) 0.0021(5) 0.0140(6) 0.0035(5) N2 0.0230(7) 0.0133(6) 0.0153(6) 0.0016(5) 0.0125(5) 0.0049(5) P1 0.0206(2) 0.01008(18) 0.01539(18) 0.00190(13) 0.01099(16) 0.00311(14) Cl1 0.0229(2) 0.0235(2) 0.01672(18) -0.00264(14) 0.00556(16) 0.00302(15) Cl2 0.01976(19) 0.0183(2) 0.02116(19) -0.00432(14) 0.00884(16) -0.00004(14) Cl3 0.0231(2) 0.0208(2) 0.0239(2) -0.00108(15) 0.01490(17) 0.00713(15) _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 N1 1.324(2) . ? C1 N2 1.329(2) . ? C1 P1 1.8787(16) . ? C2 N1 1.482(2) . ? C2 C3 1.523(2) . ? C3 N2 1.474(2) . ? C4 N1 1.460(2) . ? C5 N2 1.456(2) . ? P1 Cl3 2.0537(6) . ? P1 Cl2 2.4820(7) . ? P1 Cl1 2.2332(6) . ? 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 C1 N2 111.72(14) . . ? N1 C1 P1 131.40(12) . . ? N2 C1 P1 116.88(11) . . ? N1 C2 C3 103.54(13) . . ? N2 C3 C2 102.63(13) . . ? C1 N1 C4 129.72(15) . . ? C1 N1 C2 110.49(13) . . ? C4 N1 C2 117.81(14) . . ? C1 N2 C5 127.57(14) . . ? C1 N2 C3 111.31(13) . . ? C5 N2 C3 119.90(14) . . ? C1 P1 Cl3 103.22(5) . . ? C1 P1 Cl1 88.25(5) . . ? Cl3 P1 Cl1 92.48(3) . . ? C1 P1 Cl2 82.43(5) . . ? Cl3 P1 Cl2 90.19(2) . . ? Cl1 P1 Cl2 170.66(2) . . ? data_try5 _database_code_depnum_ccdc_archive 'CCDC 895223' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H20 Cl2 N4 Pd' _chemical_formula_weight 373.60 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9858(4) _cell_length_b 12.0174(6) _cell_length_c 13.4315(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.706(3) _cell_angle_gamma 90.00 _cell_volume 1402.90(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9681 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 30.47 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.769 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 1.688 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5516 _exptl_absorpt_correction_T_max 0.5516 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 93989 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0165 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 30.51 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 4274 _reflns_number_gt 3890 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+5.7000P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4274 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0773 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 2.231 _refine_diff_density_min -0.687 _refine_diff_density_rms 0.122 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 Pd Pd 0.079408(19) 0.340826(15) 0.159235(13) 0.00845(6) Uani 1 1 d . . . Cl1 Cl -0.17804(7) 0.27490(5) 0.10235(5) 0.01464(12) Uani 1 1 d . . . Cl2 Cl 0.18389(7) 0.19388(5) 0.07955(5) 0.01498(12) Uani 1 1 d . . . C1 C 0.2890(3) 0.4059(2) 0.20649(18) 0.0109(4) Uani 1 1 d . . . C2 C 0.5170(3) 0.4750(2) 0.3117(2) 0.0171(5) Uani 1 1 d . . . H21 H 0.516(4) 0.545(3) 0.344(3) 0.023(10) Uiso 1 1 d . . . H22 H 0.599(6) 0.433(4) 0.351(4) 0.042(13) Uiso 1 1 d . . . C3 C 0.5232(3) 0.4859(3) 0.1993(2) 0.0196(5) Uani 1 1 d . . . H31 H 0.603(5) 0.441(4) 0.180(3) 0.033(11) Uiso 1 1 d . . . H32 H 0.532(6) 0.562(4) 0.180(4) 0.047(14) Uiso 1 1 d . . . C4 C 0.3195(3) 0.3945(2) 0.39535(19) 0.0151(5) Uani 1 1 d . . . H43 H 0.245(4) 0.338(3) 0.380(3) 0.013(8) Uiso 1 1 d . . . H42 H 0.281(4) 0.457(3) 0.419(3) 0.021(9) Uiso 1 1 d . . . H41 H 0.404(5) 0.370(3) 0.444(3) 0.024(10) Uiso 1 1 d . . . C5 C 0.3277(4) 0.4442(3) 0.0321(2) 0.0209(5) Uani 1 1 d . . . H53 H 0.237(5) 0.411(4) 0.004(3) 0.025(10) Uiso 1 1 d . . . H52 H 0.401(5) 0.403(3) 0.008(3) 0.024(10) Uiso 1 1 d . . . H51 H 0.330(5) 0.524(4) 0.006(3) 0.030(11) Uiso 1 1 d . . . C6 C 0.0035(3) 0.4624(2) 0.23218(18) 0.0104(4) Uani 1 1 d . . . C7 C -0.0749(3) 0.5542(2) 0.3623(2) 0.0156(5) Uani 1 1 d . . . H72 H -0.173(5) 0.559(3) 0.385(3) 0.023(10) Uiso 1 1 d . . . H71 H 0.011(4) 0.561(3) 0.421(3) 0.022(9) Uiso 1 1 d . . . C8 C -0.0627(3) 0.6379(2) 0.2796(2) 0.0160(5) Uani 1 1 d . . . H82 H -0.001(4) 0.698(3) 0.304(3) 0.021(9) Uiso 1 1 d . . . H81 H -0.158(5) 0.660(3) 0.243(3) 0.027(11) Uiso 1 1 d . . . C9 C -0.0701(3) 0.3428(2) 0.3634(2) 0.0165(5) Uani 1 1 d . . . H93 H -0.165(4) 0.343(3) 0.389(3) 0.007(7) Uiso 1 1 d . . . H92 H 0.016(4) 0.336(3) 0.424(3) 0.014(8) Uiso 1 1 d . . . H91 H -0.064(4) 0.287(3) 0.318(3) 0.019(9) Uiso 1 1 d . . . C10 C 0.0705(3) 0.6230(2) 0.1349(2) 0.0181(5) Uani 1 1 d . . . H103 H 0.089(4) 0.569(3) 0.088(3) 0.016(9) Uiso 1 1 d . . . H102 H 0.172(4) 0.656(3) 0.169(3) 0.018(9) Uiso 1 1 d . . . H101 H -0.001(5) 0.681(4) 0.101(3) 0.027(10) Uiso 1 1 d . . . N1 N 0.3691(2) 0.41885(19) 0.30337(17) 0.0137(4) Uani 1 1 d . . . N2 N 0.3715(3) 0.4441(2) 0.14350(17) 0.0162(4) Uani 1 1 d . . . N3 N 0.0084(3) 0.57046(18) 0.21294(17) 0.0133(4) Uani 1 1 d . . . N4 N -0.0615(2) 0.44724(19) 0.31124(17) 0.0132(4) Uani 1 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 Pd 0.00901(9) 0.00781(9) 0.00870(9) -0.00071(6) 0.00259(6) -0.00120(6) Cl1 0.0120(2) 0.0159(3) 0.0163(3) -0.0037(2) 0.0039(2) -0.0039(2) Cl2 0.0140(2) 0.0135(3) 0.0174(3) -0.0030(2) 0.0039(2) 0.0007(2) C1 0.0112(10) 0.0085(10) 0.0133(10) -0.0002(8) 0.0037(8) -0.0002(8) C2 0.0098(10) 0.0201(13) 0.0202(12) -0.0031(10) 0.0017(9) -0.0035(9) C3 0.0133(11) 0.0249(14) 0.0216(12) -0.0016(11) 0.0063(9) -0.0074(10) C4 0.0169(11) 0.0164(12) 0.0113(10) 0.0005(9) 0.0023(9) 0.0006(9) C5 0.0218(13) 0.0282(15) 0.0137(11) 0.0010(10) 0.0060(10) -0.0072(11) C6 0.0085(9) 0.0104(10) 0.0114(10) -0.0009(8) 0.0010(7) -0.0019(8) C7 0.0164(11) 0.0144(12) 0.0174(11) -0.0046(9) 0.0068(9) 0.0019(9) C8 0.0167(11) 0.0106(11) 0.0204(12) -0.0032(9) 0.0038(9) 0.0025(9) C9 0.0209(12) 0.0143(12) 0.0162(11) 0.0001(9) 0.0082(9) -0.0006(9) C10 0.0209(12) 0.0132(12) 0.0201(12) 0.0044(10) 0.0050(10) -0.0015(10) N1 0.0117(9) 0.0155(10) 0.0133(9) -0.0005(8) 0.0019(7) -0.0032(8) N2 0.0127(9) 0.0223(11) 0.0140(10) -0.0001(8) 0.0038(8) -0.0062(8) N3 0.0156(10) 0.0092(10) 0.0158(9) 0.0003(7) 0.0049(8) -0.0002(7) N4 0.0148(9) 0.0119(10) 0.0147(9) -0.0024(8) 0.0074(8) 0.0000(8) _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 Pd C6 1.975(2) . ? Pd C1 1.988(2) . ? Pd Cl2 2.3781(6) . ? Pd Cl1 2.3803(6) . ? C1 N1 1.327(3) . ? C1 N2 1.340(3) . ? C2 N1 1.469(3) . ? C2 C3 1.531(4) . ? C3 N2 1.467(3) . ? C4 N1 1.446(3) . ? C5 N2 1.448(3) . ? C6 N3 1.327(3) . ? C6 N4 1.348(3) . ? C7 N4 1.477(3) . ? C7 C8 1.523(4) . ? C8 N3 1.468(3) . ? C9 N4 1.449(3) . ? C10 N3 1.451(3) . ? 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 Pd C1 88.24(10) . . ? C6 Pd Cl2 176.65(7) . . ? C1 Pd Cl2 89.16(7) . . ? C6 Pd Cl1 88.60(7) . . ? C1 Pd Cl1 176.28(7) . . ? Cl2 Pd Cl1 94.07(2) . . ? N1 C1 N2 109.2(2) . . ? N1 C1 Pd 126.41(18) . . ? N2 C1 Pd 124.36(18) . . ? N1 C2 C3 102.9(2) . . ? N2 C3 C2 102.3(2) . . ? N3 C6 N4 109.2(2) . . ? N3 C6 Pd 126.48(18) . . ? N4 C6 Pd 124.36(18) . . ? N4 C7 C8 101.9(2) . . ? N3 C8 C7 101.8(2) . . ? C1 N1 C4 127.3(2) . . ? C1 N1 C2 112.6(2) . . ? C4 N1 C2 119.8(2) . . ? C1 N2 C5 127.2(2) . . ? C1 N2 C3 112.7(2) . . ? C5 N2 C3 120.1(2) . . ? C6 N3 C10 127.2(2) . . ? C6 N3 C8 112.3(2) . . ? C10 N3 C8 120.4(2) . . ? C6 N4 C9 125.8(2) . . ? C6 N4 C7 110.6(2) . . ? C9 N4 C7 120.6(2) . . ? data_try6 _database_code_depnum_ccdc_archive 'CCDC 895224' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H11 F4 N2 P' _chemical_formula_weight 206.13 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' F F 0.0171 0.0103 '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' N N 0.0061 0.0033 '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 7.375(3) _cell_length_b 7.560(2) _cell_length_c 8.6846(15) _cell_angle_alpha 74.688(16) _cell_angle_beta 76.04(2) _cell_angle_gamma 62.60(2) _cell_volume 410.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 16.56 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.70 _exptl_crystal_size_min 0.60 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.351 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7207 _exptl_absorpt_correction_T_max 0.8172 _exptl_absorpt_process_details SADABS _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 'Bruker APEX-II CCD' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 2344 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 1875 _reflns_number_gt 1767 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1100P)^2^+0.2500P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1875 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.1506 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.062 _refine_diff_density_min -0.672 _refine_diff_density_rms 0.097 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 0.0584(3) 0.4513(3) 0.2481(2) 0.0204(4) Uani 1 1 d . . . C2 C -0.2157(4) 0.3276(4) 0.3862(4) 0.0383(5) Uani 1 1 d . . . H23 H -0.287(8) 0.344(7) 0.492(6) 0.088(14) Uiso 1 1 d . . . H22 H -0.123(6) 0.187(6) 0.399(5) 0.062(10) Uiso 1 1 d . . . H21 H -0.309(7) 0.353(6) 0.325(5) 0.073(12) Uiso 1 1 d . . . C3 C 0.2385(4) 0.6805(4) 0.1236(3) 0.0353(5) Uani 1 1 d . . . H33 H 0.354(7) 0.573(7) 0.121(5) 0.074(12) Uiso 1 1 d . . . H32 H 0.202(6) 0.771(6) 0.030(5) 0.072(12) Uiso 1 1 d . . . H31 H 0.247(7) 0.777(7) 0.175(5) 0.082(14) Uiso 1 1 d . . . C4 C -0.2578(3) 0.6820(3) 0.3529(3) 0.0285(4) Uani 1 1 d . . . H42 H -0.369(5) 0.735(4) 0.300(4) 0.032(7) Uiso 1 1 d . . . H41 H -0.301(5) 0.693(5) 0.460(5) 0.051(9) Uiso 1 1 d . . . C5 C -0.1194(3) 0.7891(3) 0.2741(3) 0.0315(5) Uani 1 1 d . . . H52 H -0.174(4) 0.897(4) 0.186(4) 0.034(7) Uiso 1 1 d . . . H51 H -0.092(5) 0.843(5) 0.347(4) 0.045(8) Uiso 1 1 d . . . N1 N -0.1234(3) 0.4709(3) 0.3333(2) 0.0263(4) Uani 1 1 d . . . N2 N 0.0727(3) 0.6266(3) 0.2149(2) 0.0262(4) Uani 1 1 d . . . P1 P 0.26741(7) 0.20742(7) 0.18099(6) 0.0236(2) Uani 1 1 d . . . H1P H 0.414(3) 0.037(3) 0.132(2) 0.005(4) Uiso 1 1 d . . . F1 F 0.2300(2) 0.08315(19) 0.36213(16) 0.0345(3) Uani 1 1 d . . . F2 F 0.0897(2) 0.1752(2) 0.12550(18) 0.0367(4) Uani 1 1 d . . . F3 F 0.2986(2) 0.3382(2) 0.00305(15) 0.0340(3) Uani 1 1 d . . . F4 F 0.43797(19) 0.2466(2) 0.24054(16) 0.0342(3) Uani 1 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 C1 0.0200(8) 0.0241(9) 0.0161(8) -0.0051(6) -0.0013(6) -0.0084(7) C2 0.0281(10) 0.0418(13) 0.0465(14) -0.0081(10) 0.0050(9) -0.0209(10) C3 0.0349(11) 0.0338(12) 0.0386(12) -0.0062(9) 0.0040(9) -0.0202(10) C4 0.0221(9) 0.0317(11) 0.0244(10) -0.0119(8) 0.0011(7) -0.0037(8) C5 0.0324(11) 0.0258(10) 0.0298(10) -0.0110(8) 0.0019(8) -0.0067(9) N1 0.0197(7) 0.0284(9) 0.0265(8) -0.0068(6) 0.0038(6) -0.0090(7) N2 0.0250(8) 0.0246(8) 0.0267(8) -0.0084(6) 0.0027(6) -0.0097(7) P1 0.0225(3) 0.0237(3) 0.0203(3) -0.0078(2) -0.0008(2) -0.0053(2) F1 0.0380(7) 0.0267(7) 0.0270(7) -0.0006(5) -0.0009(5) -0.0077(6) F2 0.0378(7) 0.0355(7) 0.0430(8) -0.0171(6) -0.0082(6) -0.0142(6) F3 0.0380(7) 0.0357(7) 0.0197(6) -0.0083(5) 0.0047(5) -0.0109(6) F4 0.0204(6) 0.0442(8) 0.0359(7) -0.0142(6) -0.0031(5) -0.0085(5) _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 N1 1.328(2) . ? C1 N2 1.328(2) . ? C1 P1 1.906(2) . ? C2 N1 1.454(3) . ? C3 N2 1.453(3) . ? C4 N1 1.471(3) . ? C4 C5 1.515(3) . ? C5 N2 1.470(3) . ? P1 F3 1.6278(14) . ? P1 F2 1.6337(14) . ? P1 F4 1.6353(14) . ? P1 F1 1.6378(13) . ? 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 C1 N2 110.17(17) . . ? N1 C1 P1 124.93(15) . . ? N2 C1 P1 124.90(14) . . ? N1 C4 C5 102.89(16) . . ? N2 C5 C4 103.11(17) . . ? C1 N1 C2 130.33(19) . . ? C1 N1 C4 111.85(17) . . ? C2 N1 C4 117.11(18) . . ? C1 N2 C3 130.36(18) . . ? C1 N2 C5 111.80(17) . . ? C3 N2 C5 117.71(18) . . ? F3 P1 F2 89.67(8) . . ? F3 P1 F4 90.85(8) . . ? F2 P1 F4 177.71(7) . . ? F3 P1 F1 178.00(7) . . ? F2 P1 F1 90.36(8) . . ? F4 P1 F1 89.05(8) . . ? F3 P1 C1 88.73(8) . . ? F2 P1 C1 88.63(8) . . ? F4 P1 C1 89.15(8) . . ? F1 P1 C1 89.27(8) . . ? data_try7 _database_code_depnum_ccdc_archive 'CCDC 895225' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H10 Cl4 N2 Si' _chemical_formula_weight 268.04 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' Si Si 0.0817 0.0704 '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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.8424(6) _cell_length_b 12.6500(6) _cell_length_c 13.2356(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2150.21(17) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6170 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 23.07 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.163 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6664 _exptl_absorpt_correction_T_max 0.9127 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 53047 _diffrn_reflns_av_R_equivalents 0.1073 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 23.25 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.991 _reflns_number_total 1528 _reflns_number_gt 1247 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+1.5000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1528 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.335 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.068 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 Si Si 0.66199(7) 0.16555(6) 0.28989(7) 0.0184(2) Uani 1 1 d . . . Cl1 Cl 0.59551(7) 0.26387(6) 0.16868(6) 0.0272(2) Uani 1 1 d . . . Cl2 Cl 0.66371(7) 0.03280(6) 0.19810(7) 0.0291(2) Uani 1 1 d . . . Cl3 Cl 0.80077(6) 0.24926(6) 0.28846(7) 0.0266(2) Uani 1 1 d . . . Cl4 Cl 0.71268(6) 0.07349(6) 0.42338(6) 0.0256(2) Uani 1 1 d . . . C1 C 0.5421(2) 0.2033(2) 0.3698(2) 0.0182(7) Uani 1 1 d . . . C2 C 0.3874(3) 0.1894(3) 0.4593(3) 0.0239(8) Uani 1 1 d . . . H22 H 0.316(3) 0.184(3) 0.435(2) 0.019(9) Uiso 1 1 d . . . H21 H 0.387(2) 0.157(3) 0.523(3) 0.023(9) Uiso 1 1 d . . . C3 C 0.4262(3) 0.3024(3) 0.4659(3) 0.0232(8) Uani 1 1 d . . . H32 H 0.436(2) 0.327(2) 0.533(3) 0.008(8) Uiso 1 1 d . . . H31 H 0.381(3) 0.349(3) 0.427(3) 0.026(9) Uiso 1 1 d . . . C4 C 0.4492(3) 0.0289(3) 0.3605(3) 0.0264(8) Uani 1 1 d . . . H43 H 0.509(3) 0.001(3) 0.337(3) 0.023(9) Uiso 1 1 d . . . H42 H 0.398(3) 0.025(3) 0.310(3) 0.054(13) Uiso 1 1 d . . . H41 H 0.423(3) -0.014(4) 0.422(4) 0.064(14) Uiso 1 1 d . . . C5 C 0.5945(3) 0.3893(3) 0.4103(3) 0.0267(8) Uani 1 1 d . . . H53 H 0.651(3) 0.380(3) 0.370(3) 0.031(10) Uiso 1 1 d . . . H52 H 0.554(3) 0.447(3) 0.390(3) 0.030(10) Uiso 1 1 d . . . H51 H 0.619(3) 0.405(3) 0.478(3) 0.035(10) Uiso 1 1 d . . . N1 N 0.4633(2) 0.1393(2) 0.3909(2) 0.0210(6) Uani 1 1 d . . . N2 N 0.5275(2) 0.2972(2) 0.41260(19) 0.0205(6) Uani 1 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 Si 0.0214(5) 0.0140(5) 0.0198(5) -0.0014(4) 0.0009(4) -0.0015(4) Cl1 0.0351(5) 0.0242(4) 0.0224(5) 0.0041(3) -0.0027(4) 0.0013(4) Cl2 0.0353(5) 0.0196(4) 0.0323(5) -0.0085(4) 0.0033(4) -0.0028(4) Cl3 0.0272(5) 0.0249(5) 0.0277(5) -0.0011(3) 0.0013(4) -0.0063(4) Cl4 0.0247(5) 0.0228(5) 0.0294(5) 0.0072(3) -0.0015(4) 0.0023(3) C1 0.0229(18) 0.0169(17) 0.0149(17) 0.0023(13) -0.0043(14) 0.0017(14) C2 0.023(2) 0.0278(19) 0.021(2) -0.0014(16) 0.0030(16) 0.0002(16) C3 0.026(2) 0.0225(18) 0.021(2) 0.0011(16) 0.0028(15) 0.0049(16) C4 0.028(2) 0.0185(18) 0.033(2) -0.0064(17) 0.0028(19) -0.0044(16) C5 0.037(2) 0.0139(18) 0.030(2) 0.0007(16) 0.0048(19) 0.0001(17) N1 0.0222(15) 0.0166(14) 0.0241(16) -0.0026(11) 0.0011(12) -0.0015(12) N2 0.0264(15) 0.0134(14) 0.0218(15) -0.0026(11) 0.0039(12) -0.0016(12) _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 Si C1 1.928(3) . ? Si Cl2 2.0727(11) . ? Si Cl3 2.0732(12) . ? Si Cl1 2.2022(12) . ? Si Cl4 2.2139(12) . ? C1 N2 1.329(4) . ? C1 N1 1.325(4) . ? C2 N1 1.474(4) . ? C2 C3 1.517(5) . ? C3 N2 1.481(4) . ? C4 N1 1.465(4) . ? C5 N2 1.449(4) . ? 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 C1 Si Cl2 122.04(10) . . ? C1 Si Cl3 124.41(10) . . ? Cl2 Si Cl3 113.54(5) . . ? C1 Si Cl1 87.14(10) . . ? Cl2 Si Cl1 91.99(5) . . ? Cl3 Si Cl1 92.19(5) . . ? C1 Si Cl4 85.83(10) . . ? Cl2 Si Cl4 92.21(5) . . ? Cl3 Si Cl4 91.33(5) . . ? Cl1 Si Cl4 172.95(6) . . ? N2 C1 N1 110.4(3) . . ? N2 C1 Si 124.6(2) . . ? N1 C1 Si 125.0(2) . . ? N1 C2 C3 102.9(3) . . ? N2 C3 C2 102.7(3) . . ? C1 N1 C4 128.2(3) . . ? C1 N1 C2 111.8(3) . . ? C4 N1 C2 119.8(3) . . ? C1 N2 C5 128.8(3) . . ? C1 N2 C3 111.5(3) . . ? C5 N2 C3 119.7(3) . . ?