Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm # SUBMISSION DETAILS _journal_coden_Cambridge 1350 #============================================================================== _audit_creation_method 'manual editing of form.cif' _publ_contact_author_name 'Krzysztof Wozniak' _publ_contact_author_address ; Chemistry Department, Warsaw University, ul. Pasteura 1, 02-093 Warszawa, Poland ; _publ_contact_author_email kwozniak@chem.uw.edu.pl _publ_contact_author_fax 48(22)8222892 _publ_contact_author_phone 48(22)8220292 _publ_contact_letter ; Please consider this CIF submission as a supplementary information for publication in CrystEngComm ; # TITLE AND AUTHOR LIST _publ_section_title ; On Polymorphism and Planarity of Benzidine Dihydrochloride ; _publ_section_title_footnote ; Contribution No. ... ; loop_ _publ_author_name _publ_author_address 'Lukasz Dobrzycki' ; Chemistry Department, Warsaw University, ul. Pasteura 1, 02-093 Warszawa, Poland ; K.Wozniak ; Chemistry Department, Warsaw University, ul. Pasteura 1, 02-093 Warszawa, Poland. ; _publ_section_abstract ; ? ; _publ_section_experimental ; ? ; _publ_section_comment ; ? ; _publ_section_references ; ? ; _publ_section_figure_captions ; ? ; ############################################################# data_1a_120 _database_code_depnum_ccdc_archive 'CCDC 618057' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cl2 N2' _chemical_formula_weight 257.15 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.0000 '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 6.5705(11) _cell_length_b 7.6756(14) _cell_length_c 12.6098(18) _cell_angle_alpha 85.165(13) _cell_angle_beta 76.785(13) _cell_angle_gamma 73.868(16) _cell_volume 594.58(17) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.519 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.85 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 KM4CCD _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.6479 _diffrn_standards_number '1 frame' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 14508 _diffrn_reflns_av_R_equivalents 0.0107 _diffrn_reflns_av_sigmaI/netI 0.0079 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3452 _reflns_number_gt 3131 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material SHELXTL-97 _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^)+(0.0468P)^2^+0.0795P] 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 SHELXL _refine_ls_extinction_coef 0.074(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3452 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0243 _refine_ls_R_factor_gt 0.0218 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.03971(3) 0.17640(2) 0.080928(13) 0.01292(7) Uani 1 1 d . . . Cl2 Cl 0.46084(3) 0.32459(2) 0.911442(13) 0.01369(7) Uani 1 1 d . . . N1 N 1.10319(11) 0.56602(9) 0.11552(5) 0.01224(13) Uani 1 1 d . . . N2 N 0.41134(11) 0.92387(9) 0.88626(5) 0.01268(13) Uani 1 1 d . . . C1 C 0.99392(12) 0.61926(10) 0.22723(6) 0.01067(14) Uani 1 1 d . . . C2 C 0.93435(12) 0.49065(10) 0.30275(6) 0.01262(14) Uani 1 1 d . . . C3 C 0.83649(12) 0.54304(10) 0.40961(6) 0.01247(14) Uani 1 1 d . . . C4 C 0.79494(12) 0.72235(10) 0.44152(6) 0.01071(13) Uani 1 1 d . . . C5 C 0.85604(12) 0.84863(10) 0.36231(6) 0.01291(14) Uani 1 1 d . . . C6 C 0.95750(12) 0.79762(10) 0.25581(6) 0.01276(14) Uani 1 1 d . . . C7 C 0.51270(12) 0.87111(10) 0.77336(6) 0.01119(14) Uani 1 1 d . . . C8 C 0.63209(12) 0.97726(10) 0.70655(6) 0.01357(14) Uani 1 1 d . . . C9 C 0.72207(12) 0.92866(10) 0.59858(6) 0.01352(14) Uani 1 1 d . . . C10 C 0.69376(12) 0.77577(10) 0.55622(6) 0.01093(14) Uani 1 1 d . . . C11 C 0.57249(12) 0.67204(10) 0.62650(6) 0.01326(14) Uani 1 1 d . . . C12 C 0.48199(12) 0.71832(10) 0.73493(6) 0.01302(14) Uani 1 1 d . . . H1A H 1.102(2) 0.459(2) 0.1028(11) 0.025(3) Uiso 1 1 d . . . H1B H 1.238(2) 0.5746(18) 0.1001(11) 0.022(3) Uiso 1 1 d . . . H1C H 1.041(2) 0.6414(19) 0.0648(11) 0.021(3) Uiso 1 1 d . . . H2 H 0.967(2) 0.3652(16) 0.2839(9) 0.022(3) Uiso 1 1 d . . . H2A H 0.414(2) 1.033(2) 0.8964(11) 0.026(3) Uiso 1 1 d . . . H2B H 0.479(2) 0.8498(18) 0.9357(11) 0.020(3) Uiso 1 1 d . . . H2C H 0.274(2) 0.9178(18) 0.9052(11) 0.021(3) Uiso 1 1 d . . . H3 H 0.804(2) 0.4514(16) 0.4620(10) 0.023(3) Uiso 1 1 d . . . H5 H 0.8224(19) 0.9748(15) 0.3787(9) 0.019(3) Uiso 1 1 d . . . H6 H 0.999(2) 0.8835(17) 0.2030(10) 0.028(3) Uiso 1 1 d . . . H8 H 0.654(2) 1.0793(17) 0.7335(10) 0.025(3) Uiso 1 1 d . . . H9 H 0.805(2) 1.0028(17) 0.5546(10) 0.025(3) Uiso 1 1 d . . . H11 H 0.545(2) 0.5682(16) 0.6011(9) 0.024(3) Uiso 1 1 d . . . H12 H 0.398(2) 0.6481(17) 0.7797(10) 0.025(3) Uiso 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 Cl1 0.01479(11) 0.01178(11) 0.01207(10) -0.00023(6) -0.00047(7) -0.00531(7) Cl2 0.01517(11) 0.01305(11) 0.01284(10) -0.00004(6) -0.00078(7) -0.00566(7) N1 0.0151(3) 0.0130(3) 0.0084(3) -0.0014(2) -0.0003(2) -0.0050(2) N2 0.0147(3) 0.0144(3) 0.0085(3) -0.0016(2) -0.0005(2) -0.0044(2) C1 0.0109(3) 0.0132(3) 0.0077(3) -0.0008(2) -0.0010(2) -0.0035(2) C2 0.0156(3) 0.0117(3) 0.0107(3) -0.0005(2) -0.0017(2) -0.0046(2) C3 0.0152(3) 0.0122(3) 0.0100(3) 0.0007(2) -0.0012(2) -0.0052(2) C4 0.0107(3) 0.0123(3) 0.0091(3) -0.0009(2) -0.0016(2) -0.0032(2) C5 0.0162(3) 0.0113(3) 0.0110(3) -0.0003(2) -0.0020(2) -0.0039(2) C6 0.0163(3) 0.0117(3) 0.0103(3) 0.0009(2) -0.0019(2) -0.0049(2) C7 0.0111(3) 0.0134(3) 0.0083(3) -0.0012(2) -0.0011(2) -0.0026(2) C8 0.0155(3) 0.0148(3) 0.0113(3) -0.0023(2) -0.0006(2) -0.0068(3) C9 0.0154(3) 0.0147(3) 0.0109(3) -0.0013(2) 0.0003(2) -0.0070(3) C10 0.0109(3) 0.0125(3) 0.0090(3) -0.0009(2) -0.0013(2) -0.0029(2) C11 0.0147(3) 0.0136(3) 0.0116(3) -0.0016(2) -0.0003(2) -0.0057(2) C12 0.0147(3) 0.0133(3) 0.0108(3) -0.0003(2) -0.0001(2) -0.0056(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.4623(9) . ? N1 H1A 0.850(15) . ? N1 H1B 0.882(15) . ? N1 H1C 0.916(13) . ? N2 C7 1.4656(9) . ? N2 H2A 0.863(15) . ? N2 H2B 0.913(13) . ? N2 H2C 0.891(14) . ? C1 C2 1.3858(10) . ? C1 C6 1.3868(10) . ? C2 C3 1.3937(10) . ? C2 H2 0.964(12) . ? C3 C4 1.4018(10) . ? C3 H3 0.957(12) . ? C4 C5 1.4029(10) . ? C4 C10 1.4869(11) . ? C5 C6 1.3912(10) . ? C5 H5 0.961(11) . ? C6 H6 0.947(13) . ? C7 C12 1.3868(10) . ? C7 C8 1.3879(11) . ? C8 C9 1.3920(10) . ? C8 H8 0.940(12) . ? C9 C10 1.4033(10) . ? C9 H9 0.955(13) . ? C10 C11 1.4017(10) . ? C11 C12 1.3936(10) . ? C11 H11 0.958(12) . ? C12 H12 0.942(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 C1 N1 H1A 112.3(9) . . ? C1 N1 H1B 111.7(9) . . ? H1A N1 H1B 109.7(12) . . ? C1 N1 H1C 112.5(8) . . ? H1A N1 H1C 106.6(13) . . ? H1B N1 H1C 103.7(12) . . ? C7 N2 H2A 110.7(9) . . ? C7 N2 H2B 112.8(8) . . ? H2A N2 H2B 107.3(13) . . ? C7 N2 H2C 112.6(8) . . ? H2A N2 H2C 108.5(13) . . ? H2B N2 H2C 104.6(12) . . ? C2 C1 C6 121.44(7) . . ? C2 C1 N1 119.72(7) . . ? C6 C1 N1 118.82(7) . . ? C1 C2 C3 118.79(7) . . ? C1 C2 H2 121.4(7) . . ? C3 C2 H2 119.7(7) . . ? C2 C3 C4 121.52(7) . . ? C2 C3 H3 118.0(7) . . ? C4 C3 H3 120.4(7) . . ? C3 C4 C5 117.86(6) . . ? C3 C4 C10 120.97(7) . . ? C5 C4 C10 121.16(7) . . ? C6 C5 C4 121.27(7) . . ? C6 C5 H5 117.5(7) . . ? C4 C5 H5 121.1(7) . . ? C1 C6 C5 119.10(7) . . ? C1 C6 H6 120.1(7) . . ? C5 C6 H6 120.7(7) . . ? C12 C7 C8 121.48(7) . . ? C12 C7 N2 119.00(7) . . ? C8 C7 N2 119.51(7) . . ? C7 C8 C9 118.92(7) . . ? C7 C8 H8 121.0(7) . . ? C9 C8 H8 120.1(7) . . ? C8 C9 C10 121.43(7) . . ? C8 C9 H9 117.3(7) . . ? C10 C9 H9 121.2(7) . . ? C11 C10 C9 117.82(6) . . ? C11 C10 C4 121.10(7) . . ? C9 C10 C4 121.05(7) . . ? C12 C11 C10 121.51(7) . . ? C12 C11 H11 117.4(7) . . ? C10 C11 H11 121.1(7) . . ? C7 C12 C11 118.84(7) . . ? C7 C12 H12 121.5(7) . . ? C11 C12 H12 119.6(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.22(11) . . . . ? N1 C1 C2 C3 178.02(7) . . . . ? C1 C2 C3 C4 0.85(11) . . . . ? C2 C3 C4 C5 -0.29(11) . . . . ? C2 C3 C4 C10 -178.97(7) . . . . ? C3 C4 C5 C6 -0.92(11) . . . . ? C10 C4 C5 C6 177.76(7) . . . . ? C2 C1 C6 C5 -0.95(11) . . . . ? N1 C1 C6 C5 -179.21(7) . . . . ? C4 C5 C6 C1 1.53(11) . . . . ? C12 C7 C8 C9 0.16(11) . . . . ? N2 C7 C8 C9 -178.10(7) . . . . ? C7 C8 C9 C10 0.25(11) . . . . ? C8 C9 C10 C11 -0.39(11) . . . . ? C8 C9 C10 C4 -178.51(7) . . . . ? C3 C4 C10 C11 -21.60(12) . . . . ? C5 C4 C10 C11 159.76(7) . . . . ? C3 C4 C10 C9 156.45(7) . . . . ? C5 C4 C10 C9 -22.18(12) . . . . ? C9 C10 C11 C12 0.12(11) . . . . ? C4 C10 C11 C12 178.24(7) . . . . ? C8 C7 C12 C11 -0.41(11) . . . . ? N2 C7 C12 C11 177.85(6) . . . . ? C10 C11 C12 C7 0.27(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 0.850(15) 2.368(15) 3.2099(9) 171.1(13) 1_655 N1 H1B Cl2 0.882(15) 2.289(15) 3.1415(9) 162.7(12) 2_766 N1 H1C Cl1 0.916(13) 2.283(13) 3.1833(9) 167.6(12) 2_665 N2 H2A Cl2 0.863(15) 2.371(15) 3.2303(9) 173.6(13) 1_565 N2 H2B Cl2 0.913(13) 2.299(13) 3.1810(8) 162.3(11) 2_667 N2 H2C Cl1 0.891(14) 2.334(14) 3.1937(9) 161.9(11) 2_566 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.521 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.066 data_1a_293 _database_code_depnum_ccdc_archive 'CCDC 618058' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cl2 N2' _chemical_formula_weight 257.15 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.0000 '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 6.6652(10) _cell_length_b 7.7196(12) _cell_length_c 12.572(2) _cell_angle_alpha 84.567(14) _cell_angle_beta 76.328(14) _cell_angle_gamma 74.007(14) _cell_volume 603.93(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.511 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.87 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 KM4CCD _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.6479 _diffrn_standards_number '1 frame' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 16213 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0135 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3516 _reflns_number_gt 2543 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material SHELXTL-97 _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^)+(0.0638P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.035(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3516 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.03650(4) 0.17812(3) 0.08153(2) 0.03311(10) Uani 1 1 d . . . Cl2 Cl 0.46506(4) 0.32262(3) 0.91201(2) 0.03481(10) Uani 1 1 d . . . N1 N 1.10432(17) 0.56381(14) 0.11573(7) 0.0303(2) Uani 1 1 d . . . N2 N 0.40815(17) 0.92773(14) 0.88527(7) 0.0314(2) Uani 1 1 d . . . C1 C 0.99557(16) 0.61768(14) 0.22728(7) 0.0253(2) Uani 1 1 d . . . C2 C 0.92858(19) 0.49285(15) 0.30362(8) 0.0313(2) Uani 1 1 d . . . C3 C 0.83129(19) 0.54531(15) 0.40999(8) 0.0312(2) Uani 1 1 d . . . C4 C 0.79626(15) 0.72210(13) 0.44155(7) 0.0252(2) Uani 1 1 d . . . C5 C 0.86495(19) 0.84426(15) 0.36139(8) 0.0319(2) Uani 1 1 d . . . C6 C 0.96583(19) 0.79275(15) 0.25530(8) 0.0319(2) Uani 1 1 d . . . C7 C 0.51028(16) 0.87444(14) 0.77283(7) 0.0267(2) Uani 1 1 d . . . C8 C 0.62570(19) 0.98042(16) 0.70388(9) 0.0345(2) Uani 1 1 d . . . C9 C 0.7167(2) 0.93089(16) 0.59675(9) 0.0343(2) Uani 1 1 d . . . C10 C 0.69476(15) 0.77622(13) 0.55595(7) 0.0259(2) Uani 1 1 d . . . C11 C 0.57707(19) 0.67273(16) 0.62849(8) 0.0331(2) Uani 1 1 d . . . C12 C 0.48547(19) 0.72032(15) 0.73619(8) 0.0326(2) Uani 1 1 d . . . H1A H 1.102(3) 0.458(2) 0.1045(13) 0.043(4) Uiso 1 1 d . . . H1B H 1.231(3) 0.576(2) 0.1005(13) 0.044(4) Uiso 1 1 d . . . H1C H 1.039(2) 0.651(2) 0.0626(13) 0.047(4) Uiso 1 1 d . . . H2 H 0.955(3) 0.372(2) 0.2869(13) 0.062(5) Uiso 1 1 d . . . H2A H 0.410(3) 1.038(2) 0.8945(13) 0.047(4) Uiso 1 1 d . . . H2B H 0.474(2) 0.846(2) 0.9351(13) 0.048(4) Uiso 1 1 d . . . H2C H 0.278(3) 0.919(2) 0.9052(13) 0.048(4) Uiso 1 1 d . . . H3 H 0.791(2) 0.461(2) 0.4595(11) 0.043(4) Uiso 1 1 d . . . H5 H 0.836(2) 0.963(2) 0.3770(11) 0.047(4) Uiso 1 1 d . . . H6 H 1.012(2) 0.876(2) 0.2046(12) 0.052(4) Uiso 1 1 d . . . H8 H 0.646(3) 1.085(2) 0.7285(13) 0.062(5) Uiso 1 1 d . . . H9 H 0.792(2) 1.001(2) 0.5518(11) 0.041(4) Uiso 1 1 d . . . H11 H 0.555(2) 0.570(2) 0.6059(11) 0.050(4) Uiso 1 1 d . . . H12 H 0.404(2) 0.650(2) 0.7806(12) 0.050(4) Uiso 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 Cl1 0.03903(16) 0.02865(15) 0.03073(15) -0.00146(10) 0.00018(10) -0.01387(11) Cl2 0.03983(17) 0.03148(16) 0.03259(15) -0.00126(10) -0.00045(11) -0.01479(12) N1 0.0380(5) 0.0321(5) 0.0207(4) -0.0033(3) -0.0007(3) -0.0132(4) N2 0.0375(5) 0.0344(5) 0.0210(4) -0.0040(3) -0.0009(4) -0.0108(4) C1 0.0274(5) 0.0289(5) 0.0198(4) -0.0015(3) -0.0035(3) -0.0091(4) C2 0.0426(6) 0.0267(5) 0.0252(4) -0.0028(4) -0.0024(4) -0.0134(4) C3 0.0411(6) 0.0293(5) 0.0234(4) 0.0000(4) -0.0011(4) -0.0147(4) C4 0.0256(5) 0.0281(5) 0.0221(4) -0.0021(3) -0.0035(3) -0.0084(4) C5 0.0439(6) 0.0255(5) 0.0252(4) -0.0021(4) -0.0019(4) -0.0114(4) C6 0.0429(6) 0.0282(5) 0.0238(4) 0.0017(4) -0.0019(4) -0.0136(4) C7 0.0277(5) 0.0304(5) 0.0207(4) -0.0021(3) -0.0023(3) -0.0074(4) C8 0.0430(6) 0.0366(6) 0.0269(5) -0.0071(4) 0.0006(4) -0.0202(5) C9 0.0418(6) 0.0375(6) 0.0260(5) -0.0047(4) 0.0025(4) -0.0213(5) C10 0.0267(5) 0.0281(5) 0.0219(4) -0.0024(3) -0.0026(4) -0.0076(4) C11 0.0408(6) 0.0317(6) 0.0272(5) -0.0051(4) 0.0017(4) -0.0167(5) C12 0.0388(6) 0.0313(6) 0.0266(5) -0.0020(4) 0.0024(4) -0.0149(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 N1 C1 1.4592(13) . ? N1 H1A 0.849(17) . ? N1 H1B 0.850(17) . ? N1 H1C 0.988(16) . ? N2 C7 1.4601(13) . ? N2 H2A 0.877(18) . ? N2 H2B 0.943(16) . ? N2 H2C 0.866(18) . ? C1 C6 1.3781(15) . ? C1 C2 1.3815(14) . ? C2 C3 1.3859(14) . ? C2 H2 0.938(18) . ? C3 C4 1.3992(15) . ? C3 H3 0.911(15) . ? C4 C5 1.3980(14) . ? C4 C10 1.4829(14) . ? C5 C6 1.3850(15) . ? C5 H5 0.916(15) . ? C6 H6 0.922(16) . ? C7 C12 1.3796(15) . ? C7 C8 1.3820(15) . ? C8 C9 1.3827(15) . ? C8 H8 0.945(17) . ? C9 C10 1.3993(14) . ? C9 H9 0.909(14) . ? C10 C11 1.3980(14) . ? C11 C12 1.3861(14) . ? C11 H11 0.927(15) . ? C12 H12 0.927(16) . ? 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 N1 H1A 111.8(11) . . ? C1 N1 H1B 111.0(10) . . ? H1A N1 H1B 112.0(15) . . ? C1 N1 H1C 110.0(9) . . ? H1A N1 H1C 110.5(14) . . ? H1B N1 H1C 101.0(14) . . ? C7 N2 H2A 110.7(11) . . ? C7 N2 H2B 110.4(10) . . ? H2A N2 H2B 111.5(14) . . ? C7 N2 H2C 113.5(11) . . ? H2A N2 H2C 109.0(15) . . ? H2B N2 H2C 101.6(14) . . ? C6 C1 C2 121.01(9) . . ? C6 C1 N1 118.98(9) . . ? C2 C1 N1 119.99(9) . . ? C1 C2 C3 119.12(10) . . ? C1 C2 H2 121.9(10) . . ? C3 C2 H2 118.8(10) . . ? C2 C3 C4 121.68(10) . . ? C2 C3 H3 117.8(9) . . ? C4 C3 H3 120.5(9) . . ? C5 C4 C3 117.24(9) . . ? C5 C4 C10 121.50(10) . . ? C3 C4 C10 121.25(9) . . ? C6 C5 C4 121.64(10) . . ? C6 C5 H5 118.1(9) . . ? C4 C5 H5 120.2(9) . . ? C1 C6 C5 119.29(10) . . ? C1 C6 H6 121.1(9) . . ? C5 C6 H6 119.6(9) . . ? C12 C7 C8 120.88(9) . . ? C12 C7 N2 119.18(9) . . ? C8 C7 N2 119.93(10) . . ? C7 C8 C9 119.30(10) . . ? C7 C8 H8 121.6(9) . . ? C9 C8 H8 119.1(10) . . ? C8 C9 C10 121.76(10) . . ? C8 C9 H9 118.9(9) . . ? C10 C9 H9 119.3(9) . . ? C11 C10 C9 117.08(9) . . ? C11 C10 C4 121.46(10) . . ? C9 C10 C4 121.45(9) . . ? C12 C11 C10 121.83(10) . . ? C12 C11 H11 117.1(9) . . ? C10 C11 H11 121.0(9) . . ? C7 C12 C11 119.15(10) . . ? C7 C12 H12 121.9(9) . . ? C11 C12 H12 118.9(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.39(17) . . . . ? N1 C1 C2 C3 178.09(10) . . . . ? C1 C2 C3 C4 1.01(17) . . . . ? C2 C3 C4 C5 -0.45(16) . . . . ? C2 C3 C4 C10 -179.13(10) . . . . ? C3 C4 C5 C6 -0.73(16) . . . . ? C10 C4 C5 C6 177.95(11) . . . . ? C2 C1 C6 C5 -0.75(17) . . . . ? N1 C1 C6 C5 -179.25(10) . . . . ? C4 C5 C6 C1 1.33(18) . . . . ? C12 C7 C8 C9 0.17(18) . . . . ? N2 C7 C8 C9 -178.27(11) . . . . ? C7 C8 C9 C10 0.15(19) . . . . ? C8 C9 C10 C11 -0.25(18) . . . . ? C8 C9 C10 C4 -178.83(11) . . . . ? C5 C4 C10 C11 163.09(10) . . . . ? C3 C4 C10 C11 -18.28(16) . . . . ? C5 C4 C10 C9 -18.39(16) . . . . ? C3 C4 C10 C9 160.24(10) . . . . ? C9 C10 C11 C12 0.04(17) . . . . ? C4 C10 C11 C12 178.62(11) . . . . ? C8 C7 C12 C11 -0.37(17) . . . . ? N2 C7 C12 C11 178.08(10) . . . . ? C10 C11 C12 C7 0.26(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 0.849(17) 2.372(18) 3.2140(12) 171.1(15) 1_655 N1 H1B Cl2 0.850(17) 2.332(17) 3.1597(12) 164.7(14) 2_766 N1 H1C Cl1 0.988(16) 2.213(16) 3.1836(11) 167.2(13) 2_665 N2 H2A Cl2 0.877(18) 2.360(18) 3.2312(12) 172.4(15) 1_565 N2 H2B Cl2 0.943(16) 2.270(16) 3.1828(12) 162.7(13) 2_667 N2 H2C Cl1 0.866(18) 2.377(18) 3.2110(12) 161.6(14) 2_566 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.297 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.048 data_1b_120 _database_code_depnum_ccdc_archive 'CCDC 618059' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cl2 N2' _chemical_formula_weight 257.15 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' _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 4.3029(9) _cell_length_b 5.7033(9) _cell_length_c 12.6098(18) _cell_angle_alpha 100.859(13) _cell_angle_beta 95.703(13) _cell_angle_gamma 99.229(11) _cell_volume 297.29(9) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 134 _exptl_absorpt_coefficient_mu 0.519 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.85 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 KM4CCD _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.6479 _diffrn_standards_number '1 frame' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 7056 _diffrn_reflns_av_R_equivalents 0.0097 _diffrn_reflns_av_sigmaI/netI 0.0071 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 30.00 _reflns_number_total 1721 _reflns_number_gt 1683 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material SHELXTL-97 _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^)+(0.0428P)^2^+0.3514P] 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 SHELXL _refine_ls_extinction_coef 0.27(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1721 _refine_ls_number_parameters 86 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.13651(8) 0.78469(6) 0.08470(3) 0.01395(13) Uani 1 1 d . . . N1 N 0.4752(3) 0.3331(2) 0.11466(9) 0.0133(2) Uani 1 1 d . . . C1 C 0.6333(3) 0.3853(2) 0.22697(10) 0.0112(2) Uani 1 1 d . . . C2 C 0.6048(6) 0.5921(3) 0.29829(14) 0.0379(5) Uani 1 1 d . . . H2 H 0.4877 0.7048 0.2746 0.045 Uiso 1 1 calc R . . C3 C 0.7491(5) 0.6353(3) 0.40564(13) 0.0310(4) Uani 1 1 d . . . H3 H 0.7275 0.7781 0.4548 0.037 Uiso 1 1 calc R . . C4 C 0.9229(3) 0.4762(2) 0.44259(10) 0.0114(3) Uani 1 1 d . . . C5 C 0.9465(6) 0.2699(4) 0.36776(15) 0.0422(6) Uani 1 1 d . . . H5 H 1.0653 0.1572 0.3906 0.051 Uiso 1 1 calc R . . C6 C 0.8019(5) 0.2229(4) 0.26040(13) 0.0318(5) Uani 1 1 d . . . H6 H 0.8203 0.0794 0.2109 0.038 Uiso 1 1 calc R . . H1A H 0.620(6) 0.325(4) 0.064(2) 0.026(6) Uiso 1 1 d . . . H1B H 0.350(6) 0.192(5) 0.099(2) 0.027(6) Uiso 1 1 d . . . H1C H 0.363(6) 0.449(4) 0.1038(19) 0.021(5) Uiso 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 Cl1 0.01527(18) 0.01136(18) 0.01460(18) 0.00087(11) 0.00027(11) 0.00385(11) N1 0.0175(6) 0.0130(5) 0.0086(5) 0.0012(4) -0.0010(4) 0.0035(4) C1 0.0123(6) 0.0122(6) 0.0082(5) 0.0019(4) 0.0002(4) 0.0004(4) C2 0.0747(15) 0.0232(8) 0.0146(7) -0.0055(6) -0.0175(8) 0.0314(9) C3 0.0592(12) 0.0195(8) 0.0127(7) -0.0054(5) -0.0120(7) 0.0230(8) C4 0.0115(6) 0.0128(6) 0.0092(5) 0.0015(4) 0.0004(4) 0.0017(4) C5 0.0688(15) 0.0401(11) 0.0168(8) -0.0124(7) -0.0202(8) 0.0445(11) C6 0.0484(11) 0.0317(9) 0.0138(7) -0.0097(6) -0.0119(7) 0.0303(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 N1 C1 1.4635(17) . ? N1 H1A 0.93(2) . ? N1 H1B 0.87(3) . ? N1 H1C 0.90(2) . ? C1 C6 1.366(2) . ? C1 C2 1.372(2) . ? C2 C3 1.392(2) . ? C2 H2 0.9500 . ? C3 C4 1.381(2) . ? C3 H3 0.9500 . ? C4 C5 1.387(2) . ? C4 C4 1.488(3) 2_766 ? C5 C6 1.391(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1A 112.1(15) . . ? C1 N1 H1B 110.8(16) . . ? H1A N1 H1B 106(2) . . ? C1 N1 H1C 110.7(15) . . ? H1A N1 H1C 108(2) . . ? H1B N1 H1C 110(2) . . ? C6 C1 C2 120.62(13) . . ? C6 C1 N1 119.16(12) . . ? C2 C1 N1 120.20(13) . . ? C1 C2 C3 119.40(15) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 121.80(15) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 116.92(13) . . ? C3 C4 C4 121.54(16) . 2_766 ? C5 C4 C4 121.55(16) . 2_766 ? C4 C5 C6 122.08(15) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C1 C6 C5 119.18(15) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.1(3) . . . . ? N1 C1 C2 C3 178.13(19) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C2 C3 C4 C4 179.9(2) . . . 2_766 ? C3 C4 C5 C6 -0.3(4) . . . . ? C4 C4 C5 C6 179.6(2) 2_766 . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? N1 C1 C6 C5 -178.6(2) . . . . ? C4 C5 C6 C1 0.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 0.93(2) 2.28(2) 3.1813(14) 164(2) 2_665 N1 H1B Cl1 0.87(3) 2.32(3) 3.1672(14) 164(2) 1_545 N1 H1C Cl1 0.90(2) 2.32(2) 3.2192(14) 172(2) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.481 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.081 data_1b_293 _database_code_depnum_ccdc_archive 'CCDC 618060' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cl2 N2' _chemical_formula_weight 257.15 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' _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 4.3493(8) _cell_length_b 5.7526(8) _cell_length_c 12.572(2) _cell_angle_alpha 101.564(14) _cell_angle_beta 95.572(14) _cell_angle_gamma 98.717(10) _cell_volume 301.97(9) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 134 _exptl_absorpt_coefficient_mu 0.511 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.87 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 KM4CCD _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.6479 _diffrn_standards_number '1 frame' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 8048 _diffrn_reflns_av_R_equivalents 0.0140 _diffrn_reflns_av_sigmaI/netI 0.0098 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 30.00 _reflns_number_total 1749 _reflns_number_gt 1561 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material SHELXTL_97 _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^)+(0.0494P)^2^+0.0746P] 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 SHELXL _refine_ls_extinction_coef 0.149(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1749 _refine_ls_number_parameters 86 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.14201(8) 0.78650(5) 0.08471(3) 0.03439(13) Uani 1 1 d . . . N1 N 0.4698(3) 0.3339(2) 0.11521(8) 0.0313(2) Uani 1 1 d . . . C1 C 0.6289(3) 0.3859(2) 0.22736(9) 0.0260(2) Uani 1 1 d . . . C2 C 0.6036(5) 0.5924(3) 0.30001(12) 0.0481(4) Uani 1 1 d . . . H2 H 0.4899 0.7027 0.2778 0.058 Uiso 1 1 calc R . . C3 C 0.7491(4) 0.6353(3) 0.40689(11) 0.0440(4) Uani 1 1 d . . . H3 H 0.7296 0.7750 0.4560 0.053 Uiso 1 1 calc R . . C4 C 0.9222(3) 0.4765(2) 0.44266(9) 0.0257(2) Uani 1 1 d . . . C5 C 0.9417(5) 0.2700(3) 0.36638(12) 0.0500(4) Uani 1 1 d . . . H5 H 1.0564 0.1593 0.3877 0.060 Uiso 1 1 calc R . . C6 C 0.7957(4) 0.2235(3) 0.25938(11) 0.0437(4) Uani 1 1 d . . . H6 H 0.8113 0.0832 0.2100 0.052 Uiso 1 1 calc R . . H1A H 0.616(5) 0.320(4) 0.0631(19) 0.055(6) Uiso 1 1 d . . . H1B H 0.348(5) 0.191(4) 0.1003(18) 0.055(6) Uiso 1 1 d . . . H1C H 0.362(5) 0.452(4) 0.1050(16) 0.044(5) Uiso 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 Cl1 0.0394(2) 0.02872(18) 0.03326(18) 0.00143(11) -0.00062(12) 0.01101(12) N1 0.0397(6) 0.0325(5) 0.0205(5) 0.0032(4) -0.0017(4) 0.0094(5) C1 0.0297(5) 0.0272(5) 0.0199(5) 0.0040(4) 0.0008(4) 0.0038(4) C2 0.0803(12) 0.0353(7) 0.0278(6) -0.0002(5) -0.0130(7) 0.0294(7) C3 0.0721(10) 0.0318(6) 0.0256(6) -0.0027(5) -0.0093(6) 0.0235(7) C4 0.0278(5) 0.0261(5) 0.0220(5) 0.0038(4) 0.0004(4) 0.0043(4) C5 0.0719(11) 0.0456(8) 0.0302(7) -0.0066(6) -0.0152(7) 0.0371(8) C6 0.0595(9) 0.0410(7) 0.0273(6) -0.0072(5) -0.0088(6) 0.0276(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.4612(15) . ? N1 H1A 0.96(2) . ? N1 H1B 0.88(2) . ? N1 H1C 0.91(2) . ? C1 C6 1.3638(18) . ? C1 C2 1.3721(18) . ? C2 C3 1.3861(19) . ? C2 H2 0.9300 . ? C3 C4 1.3827(18) . ? C3 H3 0.9300 . ? C4 C5 1.3884(18) . ? C4 C4 1.486(2) 2_766 ? C5 C6 1.3868(19) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? 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 N1 H1A 111.4(14) . . ? C1 N1 H1B 109.9(15) . . ? H1A N1 H1B 104.3(19) . . ? C1 N1 H1C 110.5(13) . . ? H1A N1 H1C 108.3(19) . . ? H1B N1 H1C 112.2(19) . . ? C6 C1 C2 120.62(12) . . ? C6 C1 N1 119.09(11) . . ? C2 C1 N1 120.26(11) . . ? C1 C2 C3 119.42(13) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 121.90(12) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 116.73(11) . . ? C3 C4 C4 121.65(13) . 2_766 ? C5 C4 C4 121.63(14) . 2_766 ? C6 C5 C4 122.10(13) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C1 C6 C5 119.24(12) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.1(3) . . . . ? N1 C1 C2 C3 178.20(16) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C2 C3 C4 C4 179.94(17) . . . 2_766 ? C3 C4 C5 C6 0.0(3) . . . . ? C4 C4 C5 C6 179.57(18) 2_766 . . . ? C2 C1 C6 C5 -0.4(3) . . . . ? N1 C1 C6 C5 -178.70(16) . . . . ? C4 C5 C6 C1 0.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 0.96(2) 2.25(2) 3.1826(14) 165.2(19) 2_665 N1 H1B Cl1 0.88(2) 2.33(2) 3.1851(14) 165(2) 1_545 N1 H1C Cl1 0.91(2) 2.32(2) 3.2214(13) 173.4(18) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.309 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.050 data_2_120 _database_code_depnum_ccdc_archive 'CCDC 618061' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cl2 N2' _chemical_formula_weight 257.15 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 27.4793(11) _cell_length_b 6.0280(3) _cell_length_c 7.3190(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1212.36(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description planar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.509 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 KM4CCD _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.6479 _diffrn_standards_number '1 frame' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 37294 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0068 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 30.00 _reflns_number_total 1776 _reflns_number_gt 1515 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material SHELXTL-97 _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^)+(0.0476P)^2^+0.3709P] 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 SHELXL _refine_ls_extinction_coef 0.0061(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1776 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0807 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.206334(8) 0.25787(3) 0.10819(4) 0.01901(11) Uani 1 1 d . . . N1 N 0.18119(3) 0.75332(14) 0.19972(14) 0.01725(19) Uani 1 1 d . . . C1 C 0.12794(4) 0.74954(14) 0.20897(14) 0.0145(2) Uani 1 1 d . . . C2 C 0.10139(3) 0.93249(16) 0.15241(14) 0.0162(2) Uani 1 1 d . . . C3 C 0.05094(3) 0.92850(16) 0.16907(14) 0.01555(19) Uani 1 1 d . . . C4 C 0.02693(3) 0.74350(13) 0.24072(13) 0.01327(19) Uani 1 1 d . . . C5 C 0.05467(3) 0.56051(16) 0.29485(14) 0.0158(2) Uani 1 1 d . . . C6 C 0.10518(3) 0.56298(16) 0.28004(14) 0.0164(2) Uani 1 1 d . . . H1A H 0.1940(5) 0.635(3) 0.144(2) 0.033(4) Uiso 1 1 d . . . H1B H 0.1962(7) 0.748(2) 0.317(3) 0.036(5) Uiso 1 1 d . . . H1C H 0.1927(5) 0.865(3) 0.147(2) 0.028(4) Uiso 1 1 d . . . H2 H 0.1166(5) 1.060(2) 0.1049(18) 0.022(3) Uiso 1 1 d . . . H3 H 0.0338(4) 1.054(2) 0.1281(18) 0.021(3) Uiso 1 1 d . . . H5 H 0.0400(4) 0.432(2) 0.3457(19) 0.021(3) Uiso 1 1 d . . . H6 H 0.1232(4) 0.436(2) 0.3175(19) 0.021(3) Uiso 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 Cl1 0.01185(15) 0.01366(14) 0.03151(17) -0.00030(8) -0.00275(8) -0.00027(7) N1 0.0090(4) 0.0156(4) 0.0271(5) 0.0004(3) 0.0011(3) 0.0003(3) C1 0.0090(4) 0.0161(4) 0.0184(4) -0.0016(3) 0.0005(3) 0.0001(3) C2 0.0119(4) 0.0148(4) 0.0219(5) 0.0016(4) 0.0006(3) -0.0008(3) C3 0.0115(4) 0.0146(4) 0.0205(4) 0.0018(3) -0.0008(3) 0.0007(3) C4 0.0097(4) 0.0152(4) 0.0149(4) -0.0012(3) 0.0002(3) 0.0000(3) C5 0.0124(4) 0.0149(4) 0.0202(4) 0.0017(3) 0.0015(3) -0.0003(3) C6 0.0126(4) 0.0146(4) 0.0219(5) 0.0017(3) 0.0000(3) 0.0018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.4650(13) . ? N1 H1A 0.894(17) . ? N1 H1B 0.96(2) . ? N1 H1C 0.839(16) . ? C1 C2 1.3856(13) . ? C1 C6 1.3879(13) . ? C2 C3 1.3919(12) . ? C2 H2 0.943(14) . ? C3 C4 1.3979(12) . ? C3 H3 0.940(13) . ? C4 C5 1.3982(12) . ? C4 C4 1.4860(18) 3 ? C5 C6 1.3924(13) . ? C5 H5 0.951(13) . ? C6 H6 0.952(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 C1 N1 H1A 113.6(10) . . ? C1 N1 H1B 112.9(11) . . ? H1A N1 H1B 102.2(13) . . ? C1 N1 H1C 114.2(10) . . ? H1A N1 H1C 106.6(16) . . ? H1B N1 H1C 106.3(13) . . ? C2 C1 C6 121.31(9) . . ? C2 C1 N1 119.98(8) . . ? C6 C1 N1 118.68(8) . . ? C1 C2 C3 118.98(9) . . ? C1 C2 H2 121.8(8) . . ? C3 C2 H2 119.2(8) . . ? C2 C3 C4 121.12(9) . . ? C2 C3 H3 117.3(8) . . ? C4 C3 H3 121.6(8) . . ? C3 C4 C5 118.57(9) . . ? C3 C4 C4 120.29(6) . 3 ? C5 C4 C4 121.14(6) . 3 ? C6 C5 C4 120.87(9) . . ? C6 C5 H5 117.5(7) . . ? C4 C5 H5 121.6(7) . . ? C1 C6 C5 119.14(9) . . ? C1 C6 H6 121.6(7) . . ? C5 C6 H6 119.3(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.54(15) . . . . ? N1 C1 C2 C3 -177.52(9) . . . . ? C1 C2 C3 C4 -0.30(15) . . . . ? C2 C3 C4 C5 -0.36(14) . . . . ? C2 C3 C4 C4 179.32(10) . . . 3 ? C3 C4 C5 C6 0.79(14) . . . . ? C4 C4 C5 C6 -178.89(11) 3 . . . ? C2 C1 C6 C5 -0.12(15) . . . . ? N1 C1 C6 C5 177.97(9) . . . . ? C4 C5 C6 C1 -0.56(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B Cl1 0.96(2) 2.15(2) 3.0691(10) 161.8(16) 7_566 N1 H1C Cl1 0.839(16) 2.414(16) 3.1901(9) 154.2(14) 1_565 N1 H1C Cl1 0.839(16) 2.863(14) 3.1626(9) 103.3(11) 8_665 N1 H1A Cl1 0.894(17) 2.312(17) 3.1378(9) 153.6(14) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.417 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.049 data_2_293 _database_code_depnum_ccdc_archive 'CCDC 618062' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cl2 N2' _chemical_formula_weight 257.15 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 27.459(3) _cell_length_b 6.0877(8) _cell_length_c 7.3074(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1221.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.78 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.505 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 KM4CCD _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.6479 _diffrn_standards_number '1 frame' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 39654 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0118 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 29.97 _reflns_number_total 1783 _reflns_number_gt 1231 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material SHELXTL-97 _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^)+(0.0727P)^2^+0.4919P] 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 1783 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1465 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.205962(17) 0.25667(7) 0.13427(9) 0.0471(2) Uani 1 1 d . . . N1 N 0.18138(6) 0.7513(3) 0.2234(3) 0.0415(4) Uani 1 1 d . . . C1 C 0.12792(6) 0.7486(3) 0.2258(3) 0.0333(4) Uani 1 1 d . . . C2 C 0.10198(6) 0.9283(3) 0.1667(3) 0.0389(5) Uani 1 1 d . . . C3 C 0.05157(6) 0.9252(3) 0.1766(3) 0.0368(4) Uani 1 1 d . . . C4 C 0.02694(6) 0.7434(3) 0.2448(2) 0.0290(4) Uani 1 1 d . . . C5 C 0.05399(6) 0.5630(3) 0.3023(3) 0.0357(4) Uani 1 1 d . . . C6 C 0.10440(6) 0.5656(3) 0.2943(3) 0.0381(5) Uani 1 1 d . . . H1A H 0.1994(10) 0.636(6) 0.170(5) 0.080(10) Uiso 1 1 d . . . H1B H 0.1994(10) 0.750(3) 0.340(4) 0.051(8) Uiso 1 1 d . . . H1C H 0.1982(10) 0.852(6) 0.171(5) 0.080(11) Uiso 1 1 d . . . H2 H 0.1178(8) 1.054(4) 0.119(3) 0.056(7) Uiso 1 1 d . . . H3 H 0.0317(8) 1.053(4) 0.137(3) 0.048(6) Uiso 1 1 d . . . H5 H 0.0357(8) 0.432(4) 0.355(3) 0.054(7) Uiso 1 1 d . . . H6 H 0.1222(8) 0.441(4) 0.329(3) 0.054(7) Uiso 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 Cl1 0.0267(3) 0.0333(3) 0.0813(4) -0.0011(2) -0.0082(2) -0.00082(17) N1 0.0194(7) 0.0395(9) 0.0657(12) -0.0002(9) 0.0007(7) 0.0007(7) C1 0.0188(7) 0.0365(9) 0.0445(10) -0.0027(8) 0.0009(7) -0.0003(6) C2 0.0259(9) 0.0341(9) 0.0567(12) 0.0064(9) 0.0000(8) -0.0029(7) C3 0.0240(8) 0.0350(9) 0.0514(11) 0.0059(8) -0.0025(7) 0.0003(7) C4 0.0204(7) 0.0344(9) 0.0321(8) -0.0015(8) -0.0008(6) 0.0001(7) C5 0.0252(8) 0.0347(9) 0.0473(11) 0.0054(8) 0.0033(7) 0.0001(7) C6 0.0269(9) 0.0352(9) 0.0523(12) 0.0046(9) 0.0004(8) 0.0047(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.468(2) . ? N1 H1A 0.94(3) . ? N1 H1B 0.99(3) . ? N1 H1C 0.86(3) . ? C1 C2 1.375(3) . ? C1 C6 1.382(3) . ? C2 C3 1.386(2) . ? C2 H2 0.94(3) . ? C3 C4 1.390(2) . ? C3 H3 0.99(2) . ? C4 C5 1.391(2) . ? C4 C4 1.481(3) 3 ? C5 C6 1.386(2) . ? C5 H5 1.02(2) . ? C6 H6 0.94(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 C1 N1 H1A 121.3(18) . . ? C1 N1 H1B 119.4(16) . . ? H1A N1 H1B 95(2) . . ? C1 N1 H1C 123(2) . . ? H1A N1 H1C 94(3) . . ? H1B N1 H1C 97(2) . . ? C2 C1 C6 120.88(17) . . ? C2 C1 N1 120.33(17) . . ? C6 C1 N1 118.74(16) . . ? C1 C2 C3 119.36(18) . . ? C1 C2 H2 121.3(14) . . ? C3 C2 H2 119.3(14) . . ? C2 C3 C4 121.01(17) . . ? C2 C3 H3 121.5(13) . . ? C4 C3 H3 117.5(13) . . ? C3 C4 C5 118.51(16) . . ? C3 C4 C4 120.30(12) . 3 ? C5 C4 C4 121.19(12) . 3 ? C6 C5 C4 120.81(17) . . ? C6 C5 H5 121.1(13) . . ? C4 C5 H5 118.0(13) . . ? C1 C6 C5 119.42(17) . . ? C1 C6 H6 120.4(14) . . ? C5 C6 H6 120.1(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.1(3) . . . . ? N1 C1 C2 C3 -177.6(2) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C2 C3 C4 C4 179.7(2) . . . 3 ? C3 C4 C5 C6 0.9(3) . . . . ? C4 C4 C5 C6 -179.1(2) 3 . . . ? C2 C1 C6 C5 0.5(3) . . . . ? N1 C1 C6 C5 178.19(19) . . . . ? C4 C5 C6 C1 -1.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B Cl1 0.99(3) 2.16(3) 3.078(2) 155(2) 7_566 N1 H1C Cl1 0.86(3) 2.48(4) 3.2161(19) 143(3) 1_565 N1 H1C Cl1 0.86(3) 2.71(3) 3.1614(18) 114(3) 8_665 N1 H1A Cl1 0.94(3) 2.33(4) 3.1540(18) 145(3) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.272 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.054 #=END