# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Youdong Shao' _publ_contact_author_email shaoyd@mail.ustc.edu.cn loop_ _publ_author_name 'You-Dong Song' 'Shi-Kai Tian' data_syd110701 _database_code_depnum_ccdc_archive 'CCDC 832628' #TrackingRef 'syd110701.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 N2 S' _chemical_formula_weight 204.29 _chemical_absolute_configuration ad 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.9323(3) _cell_length_b 10.0252(8) _cell_length_c 18.0127(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1071.26(14) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4762 _cell_measurement_theta_min 3.3862 _cell_measurement_theta_max 29.1923 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8975 _exptl_absorpt_correction_T_max 0.9205 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9400 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2199 _reflns_number_gt 1999 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-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^)+(0.0382P)^2^+0.1219P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(9) _refine_ls_number_reflns 2199 _refine_ls_number_parameters 133 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0783 _refine_ls_wR_factor_gt 0.0754 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.047 _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 S1 S 0.57999(7) 1.00692(5) 0.84423(3) 0.05365(15) Uani 1 1 d . . . N2 N 0.7588(4) 1.14264(18) 1.03375(11) 0.0723(5) Uani 1 1 d . . . C6 C 0.5458(3) 0.73970(19) 0.86211(11) 0.0506(5) Uani 1 1 d . . . H6 H 0.4063 0.7509 0.8394 0.061 Uiso 1 1 calc R . . N1 N 1.0454(3) 0.93762(15) 0.91494(9) 0.0438(4) Uani 1 1 d D . . C4 C 0.8943(3) 0.83315(16) 0.90668(9) 0.0374(4) Uani 1 1 d . . . C7 C 0.8385(3) 1.10589(17) 0.84182(11) 0.0444(4) Uani 1 1 d . . . C1 C 0.6101(4) 0.6142(2) 0.88483(11) 0.0591(5) Uani 1 1 d . . . H1 H 0.5149 0.5417 0.8776 0.071 Uiso 1 1 calc R . . C3 C 0.9565(3) 0.70521(17) 0.92992(10) 0.0456(4) Uani 1 1 d . . . H3 H 1.0944 0.6928 0.9535 0.055 Uiso 1 1 calc R . . C5 C 0.6840(3) 0.84987(16) 0.87231(9) 0.0394(4) Uani 1 1 d . . . C2 C 0.8169(4) 0.59698(19) 0.91840(11) 0.0558(5) Uani 1 1 d . . . H2 H 0.8625 0.5124 0.9333 0.067 Uiso 1 1 calc R . . C10 C 0.9794(4) 1.0736(2) 0.77345(12) 0.0639(6) Uani 1 1 d . . . H10B H 1.0172 0.9805 0.7736 0.096 Uiso 1 1 calc R . . H10C H 1.1151 1.1257 0.7742 0.096 Uiso 1 1 calc R . . H10A H 0.8946 1.0941 0.7295 0.096 Uiso 1 1 calc R . . C8 C 0.9750(3) 1.07549(16) 0.91236(10) 0.0427(4) Uani 1 1 d . . . H8 H 1.1118 1.1301 0.9105 0.051 Uiso 1 1 calc R . . C9 C 0.8497(3) 1.11444(18) 0.98026(11) 0.0504(4) Uani 1 1 d . . . C11 C 0.7622(4) 1.25201(19) 0.84137(13) 0.0626(6) Uani 1 1 d . . . H11B H 0.8920 1.3092 0.8425 0.094 Uiso 1 1 calc R . . H11C H 0.6701 1.2690 0.8841 0.094 Uiso 1 1 calc R . . H11A H 0.6768 1.2694 0.7971 0.094 Uiso 1 1 calc R . . H4 H 1.156(3) 0.9241(19) 0.9437(10) 0.054(6) Uiso 1 1 d 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 S1 0.0384(2) 0.0516(2) 0.0710(3) 0.0054(2) -0.0111(2) 0.0023(2) N2 0.0908(14) 0.0704(12) 0.0557(11) -0.0047(10) 0.0108(10) 0.0186(11) C6 0.0471(10) 0.0570(11) 0.0477(11) -0.0043(8) 0.0010(8) -0.0131(9) N1 0.0349(7) 0.0440(8) 0.0525(10) -0.0029(7) -0.0076(7) 0.0007(6) C4 0.0378(8) 0.0400(8) 0.0345(9) -0.0042(7) 0.0048(7) 0.0020(7) C7 0.0447(9) 0.0421(8) 0.0464(10) 0.0027(8) 0.0023(8) -0.0008(7) C1 0.0716(14) 0.0483(10) 0.0574(12) -0.0052(9) 0.0124(11) -0.0192(10) C3 0.0498(10) 0.0482(10) 0.0387(10) -0.0013(7) 0.0051(8) 0.0089(8) C5 0.0395(9) 0.0425(9) 0.0361(9) -0.0047(7) 0.0015(7) -0.0022(7) C2 0.0781(13) 0.0382(9) 0.0512(12) 0.0018(9) 0.0154(11) 0.0041(9) C10 0.0661(13) 0.0787(14) 0.0470(12) 0.0027(10) 0.0100(10) 0.0074(11) C8 0.0414(9) 0.0388(9) 0.0479(11) -0.0037(7) 0.0005(8) -0.0048(7) C9 0.0580(11) 0.0432(9) 0.0501(11) -0.0015(8) -0.0013(9) 0.0029(8) C11 0.0784(15) 0.0453(10) 0.0641(14) 0.0097(10) 0.0027(12) 0.0056(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C5 1.7650(17) . ? S1 C7 1.8272(18) . ? N2 C9 1.140(3) . ? C6 C1 1.377(3) . ? C6 C5 1.388(2) . ? C6 H6 0.9300 . ? N1 C4 1.386(2) . ? N1 C8 1.445(2) . ? N1 H4 0.849(15) . ? C4 C3 1.399(2) . ? C4 C5 1.403(2) . ? C7 C10 1.523(3) . ? C7 C11 1.533(2) . ? C7 C8 1.537(2) . ? C1 C2 1.379(3) . ? C1 H1 0.9300 . ? C3 C2 1.381(3) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C10 H10A 0.9600 . ? C8 C9 1.484(3) . ? C8 H8 0.9800 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C11 H11A 0.9600 . ? 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 C5 S1 C7 101.41(8) . . ? C1 C6 C5 121.61(19) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C4 N1 C8 122.19(13) . . ? C4 N1 H4 116.5(14) . . ? C8 N1 H4 113.4(14) . . ? N1 C4 C3 119.35(15) . . ? N1 C4 C5 122.13(15) . . ? C3 C4 C5 118.44(16) . . ? C10 C7 C11 111.17(17) . . ? C10 C7 C8 109.70(15) . . ? C11 C7 C8 110.45(16) . . ? C10 C7 S1 111.35(14) . . ? C11 C7 S1 105.73(13) . . ? C8 C7 S1 108.35(12) . . ? C6 C1 C2 119.42(19) . . ? C6 C1 H1 120.3 . . ? C2 C1 H1 120.3 . . ? C2 C3 C4 121.16(18) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C6 C5 C4 119.26(16) . . ? C6 C5 S1 117.74(14) . . ? C4 C5 S1 122.95(13) . . ? C1 C2 C3 120.09(18) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C7 C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C10 H10A 109.5 . . ? H10B C10 H10A 109.5 . . ? H10C C10 H10A 109.5 . . ? N1 C8 C9 111.72(16) . . ? N1 C8 C7 111.63(14) . . ? C9 C8 C7 111.43(15) . . ? N1 C8 H8 107.3 . . ? C9 C8 H8 107.3 . . ? C7 C8 H8 107.3 . . ? N2 C9 C8 177.8(2) . . ? C7 C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? 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 C8 N1 C4 C3 -162.15(16) . . . . ? C8 N1 C4 C5 21.1(3) . . . . ? C5 S1 C7 C10 75.93(15) . . . . ? C5 S1 C7 C11 -163.22(14) . . . . ? C5 S1 C7 C8 -44.80(13) . . . . ? C5 C6 C1 C2 -0.1(3) . . . . ? N1 C4 C3 C2 -175.84(16) . . . . ? C5 C4 C3 C2 1.1(3) . . . . ? C1 C6 C5 C4 -0.1(3) . . . . ? C1 C6 C5 S1 -177.65(15) . . . . ? N1 C4 C5 C6 176.46(16) . . . . ? C3 C4 C5 C6 -0.4(2) . . . . ? N1 C4 C5 S1 -6.1(2) . . . . ? C3 C4 C5 S1 177.07(13) . . . . ? C7 S1 C5 C6 -163.75(14) . . . . ? C7 S1 C5 C4 18.79(16) . . . . ? C6 C1 C2 C3 0.8(3) . . . . ? C4 C3 C2 C1 -1.3(3) . . . . ? C4 N1 C8 C9 72.7(2) . . . . ? C4 N1 C8 C7 -52.8(2) . . . . ? C10 C7 C8 N1 -58.26(19) . . . . ? C11 C7 C8 N1 178.86(16) . . . . ? S1 C7 C8 N1 63.49(15) . . . . ? C10 C7 C8 C9 176.06(17) . . . . ? C11 C7 C8 C9 53.18(19) . . . . ? S1 C7 C8 C9 -62.19(16) . . . . ? N1 C8 C9 N2 49(6) . . . . ? C7 C8 C9 N2 175(100) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.156 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.029 data_110726 _database_code_depnum_ccdc_archive 'CCDC 837035' #TrackingRef '110726.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 Cl N2' _chemical_formula_weight 246.73 _chemical_absolute_configuration ad 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 monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.2479(3) _cell_length_b 7.0711(4) _cell_length_c 13.0826(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.024(5) _cell_angle_gamma 90.00 _cell_volume 663.93(6) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2600 _cell_measurement_theta_min 3.1387 _cell_measurement_theta_max 28.9957 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.267 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8960 _exptl_absorpt_correction_T_max 0.9217 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6023 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2686 _reflns_number_gt 2085 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-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^)+(0.0316P)^2^+0.1478P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(9) _refine_ls_number_reflns 2686 _refine_ls_number_parameters 158 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 1.29485(11) 0.21151(19) 0.54994(6) 0.1078(4) Uani 1 1 d . . . N1 N 0.8674(3) -0.1218(3) 0.18087(17) 0.0561(6) Uani 1 1 d D . . C3 C 0.9339(3) 0.1177(3) 0.29725(17) 0.0418(5) Uani 1 1 d . . . C8 C 0.7666(3) 0.1857(3) 0.22263(16) 0.0414(5) Uani 1 1 d . . . C7 C 0.7822(4) 0.0472(4) 0.13101(18) 0.0488(6) Uani 1 1 d . . . H7 H 0.6576 0.0171 0.0955 0.059 Uiso 1 1 calc R . . C9 C 0.5868(3) 0.1420(4) 0.26862(18) 0.0541(7) Uani 1 1 d . . . H9A H 0.5778 0.0065 0.2784 0.065 Uiso 1 1 calc R . . H9B H 0.5941 0.2014 0.3359 0.065 Uiso 1 1 calc R . . C4 C 0.9850(3) -0.0620(4) 0.26903(19) 0.0488(6) Uani 1 1 d . . . N2 N 0.9890(4) 0.1769(4) -0.00161(19) 0.0790(7) Uani 1 1 d . . . C2 C 1.0257(3) 0.2027(4) 0.38453(17) 0.0522(6) Uani 1 1 d . . . H2 H 0.9913 0.3222 0.4049 0.063 Uiso 1 1 calc R . . C5 C 1.1274(4) -0.1601(4) 0.3273(3) 0.0677(8) Uani 1 1 d . . . H5 H 1.1594 -0.2814 0.3088 0.081 Uiso 1 1 calc R . . C10 C 0.4113(3) 0.2106(5) 0.2008(2) 0.0730(9) Uani 1 1 d . . . H10A H 0.3925 0.1368 0.1377 0.088 Uiso 1 1 calc R . . H10B H 0.3045 0.1910 0.2367 0.088 Uiso 1 1 calc R . . C14 C 0.8982(4) 0.1244(4) 0.05645(19) 0.0566(7) Uani 1 1 d . . . C13 C 0.7728(4) 0.3949(4) 0.1936(2) 0.0530(6) Uani 1 1 d . . . H13A H 0.7873 0.4706 0.2561 0.064 Uiso 1 1 calc R . . H13B H 0.8803 0.4174 0.1587 0.064 Uiso 1 1 calc R . . C1 C 1.1712(4) 0.1045(5) 0.4412(2) 0.0656(8) Uani 1 1 d . . . C12 C 0.5967(4) 0.4573(5) 0.1236(3) 0.0738(9) Uani 1 1 d . . . H12B H 0.6041 0.5915 0.1093 0.089 Uiso 1 1 calc R . . H12A H 0.5876 0.3900 0.0585 0.089 Uiso 1 1 calc R . . C6 C 1.2215(4) -0.0724(5) 0.4143(2) 0.0740(9) Uani 1 1 d . . . H6 H 1.3191 -0.1346 0.4544 0.089 Uiso 1 1 calc R . . C11 C 0.4245(4) 0.4182(6) 0.1741(3) 0.0889(11) Uani 1 1 d . . . H11B H 0.4291 0.4934 0.2364 0.107 Uiso 1 1 calc R . . H11A H 0.3144 0.4550 0.1275 0.107 Uiso 1 1 calc R . . H1 H 0.911(4) -0.199(3) 0.1378(18) 0.066(9) Uiso 1 1 d 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 0.0631(4) 0.1931(11) 0.0612(4) -0.0140(6) -0.0121(4) -0.0107(6) N1 0.0788(16) 0.0435(13) 0.0500(13) -0.0066(11) 0.0226(12) -0.0069(11) C3 0.0382(11) 0.0511(14) 0.0384(11) 0.0008(11) 0.0135(10) -0.0019(10) C8 0.0371(11) 0.0488(14) 0.0389(11) -0.0030(11) 0.0071(9) -0.0045(11) C7 0.0524(15) 0.0538(15) 0.0411(13) -0.0021(11) 0.0104(11) -0.0159(12) C9 0.0425(12) 0.0721(18) 0.0492(13) 0.0063(13) 0.0119(11) -0.0002(12) C4 0.0505(14) 0.0526(16) 0.0474(15) 0.0057(12) 0.0218(12) 0.0006(12) N2 0.1106(19) 0.0736(19) 0.0605(14) 0.0034(13) 0.0389(14) -0.0086(15) C2 0.0422(12) 0.0705(17) 0.0452(12) -0.0077(13) 0.0106(10) -0.0023(13) C5 0.0680(19) 0.0625(19) 0.079(2) 0.0208(16) 0.0321(17) 0.0223(15) C10 0.0383(13) 0.108(3) 0.0720(17) 0.0143(19) 0.0069(12) -0.0009(16) C14 0.0732(18) 0.0586(16) 0.0400(12) -0.0028(13) 0.0152(13) -0.0105(14) C13 0.0530(15) 0.0473(15) 0.0573(16) 0.0000(13) 0.0030(12) -0.0033(12) C1 0.0402(14) 0.112(3) 0.0453(14) 0.0025(17) 0.0086(12) -0.0023(16) C12 0.0708(19) 0.0614(18) 0.084(2) 0.0171(16) -0.0062(17) 0.0043(15) C6 0.0489(16) 0.110(3) 0.065(2) 0.026(2) 0.0157(15) 0.0197(18) C11 0.0543(19) 0.110(3) 0.099(3) 0.021(2) -0.0010(17) 0.027(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.745(3) . ? N1 C4 1.400(3) . ? N1 C7 1.457(3) . ? N1 H1 0.871(17) . ? C3 C2 1.377(3) . ? C3 C4 1.388(3) . ? C3 C8 1.524(3) . ? C8 C13 1.529(4) . ? C8 C9 1.541(3) . ? C8 C7 1.564(3) . ? C7 C14 1.478(4) . ? C7 H7 0.9800 . ? C9 C10 1.525(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C4 C5 1.382(4) . ? N2 C14 1.135(3) . ? C2 C1 1.388(4) . ? C2 H2 0.9300 . ? C5 C6 1.389(4) . ? C5 H5 0.9300 . ? C10 C11 1.515(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C13 C12 1.529(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C1 C6 1.363(4) . ? C12 C11 1.516(4) . ? C12 H12B 0.9700 . ? C12 H12A 0.9700 . ? C6 H6 0.9300 . ? C11 H11B 0.9700 . ? C11 H11A 0.9700 . ? 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 C4 N1 C7 107.0(2) . . ? C4 N1 H1 119.2(18) . . ? C7 N1 H1 112.9(18) . . ? C2 C3 C4 120.3(2) . . ? C2 C3 C8 130.0(2) . . ? C4 C3 C8 109.65(19) . . ? C3 C8 C13 114.55(18) . . ? C3 C8 C9 109.08(18) . . ? C13 C8 C9 110.3(2) . . ? C3 C8 C7 99.04(18) . . ? C13 C8 C7 114.07(19) . . ? C9 C8 C7 109.21(19) . . ? N1 C7 C14 110.7(2) . . ? N1 C7 C8 104.01(18) . . ? C14 C7 C8 112.52(19) . . ? N1 C7 H7 109.8 . . ? C14 C7 H7 109.8 . . ? C8 C7 H7 109.8 . . ? C10 C9 C8 113.0(2) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C5 C4 C3 121.3(2) . . ? C5 C4 N1 128.7(3) . . ? C3 C4 N1 110.0(2) . . ? C3 C2 C1 117.9(3) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C4 C5 C6 118.2(3) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C11 C10 C9 111.6(2) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? N2 C14 C7 177.4(3) . . ? C12 C13 C8 112.1(2) . . ? C12 C13 H13A 109.2 . . ? C8 C13 H13A 109.2 . . ? C12 C13 H13B 109.2 . . ? C8 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C6 C1 C2 122.2(3) . . ? C6 C1 Cl1 118.9(2) . . ? C2 C1 Cl1 118.9(3) . . ? C11 C12 C13 110.8(2) . . ? C11 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? C11 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? H12B C12 H12A 108.1 . . ? C1 C6 C5 120.2(3) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C10 C11 C12 111.1(3) . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? H11B C11 H11A 108.0 . . ? 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 C2 C3 C8 C13 42.8(3) . . . . ? C4 C3 C8 C13 -140.6(2) . . . . ? C2 C3 C8 C9 -81.4(3) . . . . ? C4 C3 C8 C9 95.3(2) . . . . ? C2 C3 C8 C7 164.6(2) . . . . ? C4 C3 C8 C7 -18.8(2) . . . . ? C4 N1 C7 C14 89.5(2) . . . . ? C4 N1 C7 C8 -31.6(3) . . . . ? C3 C8 C7 N1 29.6(2) . . . . ? C13 C8 C7 N1 151.8(2) . . . . ? C9 C8 C7 N1 -84.3(2) . . . . ? C3 C8 C7 C14 -90.3(2) . . . . ? C13 C8 C7 C14 31.9(3) . . . . ? C9 C8 C7 C14 155.8(2) . . . . ? C3 C8 C9 C10 178.2(2) . . . . ? C13 C8 C9 C10 51.6(3) . . . . ? C7 C8 C9 C10 -74.6(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C8 C3 C4 C5 -176.7(2) . . . . ? C2 C3 C4 N1 177.4(2) . . . . ? C8 C3 C4 N1 0.4(3) . . . . ? C7 N1 C4 C5 -162.9(3) . . . . ? C7 N1 C4 C3 20.2(3) . . . . ? C4 C3 C2 C1 1.1(3) . . . . ? C8 C3 C2 C1 177.4(2) . . . . ? C3 C4 C5 C6 -1.3(4) . . . . ? N1 C4 C5 C6 -177.9(3) . . . . ? C8 C9 C10 C11 -53.2(3) . . . . ? N1 C7 C14 N2 35(6) . . . . ? C8 C7 C14 N2 151(6) . . . . ? C3 C8 C13 C12 -176.8(2) . . . . ? C9 C8 C13 C12 -53.3(3) . . . . ? C7 C8 C13 C12 70.1(3) . . . . ? C3 C2 C1 C6 -1.6(4) . . . . ? C3 C2 C1 Cl1 178.08(19) . . . . ? C8 C13 C12 C11 56.9(3) . . . . ? C2 C1 C6 C5 0.6(4) . . . . ? Cl1 C1 C6 C5 -179.1(2) . . . . ? C4 C5 C6 C1 0.9(4) . . . . ? C9 C10 C11 C12 55.5(4) . . . . ? C13 C12 C11 C10 -57.3(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 H1 N2 0.871(17) 2.200(19) 3.048(3) 164(3) 2_745 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.231 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.029