# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Edward Tiekink' _publ_contact_author_email EDWARD.TIEKINK@UTSA.EDU _publ_section_title ; Assessing the persistence of the N-H...N hydrogen bonding leading to supramolecular chains in molecules related to the anti-malarial drug, chloroquine ; loop_ _publ_author_name 'Edward R.T. Tiekink' 'Marcus Vinicius De Souza' 'Carlos R. Kaiser' 'Karla C. Pais' 'J Wardell' ; S.M.S.V.Wardell ; # Attachment '1_Me.CIF' data_Me _database_code_depnum_ccdc_archive 'CCDC 697891' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H9 Cl N2' _chemical_formula_sum 'C10 H9 Cl N2' _chemical_formula_weight 192.64 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc ' 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 4.6812(9) _cell_length_b 14.097(4) _cell_length_c 13.296(3) _cell_angle_alpha 90 _cell_angle_beta 99.967(7) _cell_angle_gamma 90 _cell_volume 864.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 98(2) _cell_measurement_reflns_used 699 _cell_measurement_theta_min 4.3 _cell_measurement_theta_max 30.3 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.388 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.888 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 98(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 8722 _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_av_sigmaI/netI 0.012 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.1 _diffrn_reflns_theta_max 26.5 _reflns_number_total 1790 _reflns_number_gt 1756 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0422P)^2^+0.4506P] 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 1790 _refine_ls_number_parameters 122 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.030 _refine_ls_R_factor_gt 0.029 _refine_ls_wR_factor_ref 0.080 _refine_ls_wR_factor_gt 0.079 _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_restrained_S_all 1.07 _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 -0.26339(7) 0.00704(2) 0.16963(2) 0.01912(12) Uani 1 1 d . . . N1 N 0.4746(2) 0.26600(8) 0.27981(8) 0.0168(2) Uani 1 1 d . . . N2 N 0.5480(2) 0.33684(8) -0.02331(8) 0.0160(2) Uani 1 1 d D . . H2N H 0.4955 0.2958 -0.0729 0.019 Uiso 1 1 d D . . C1 C 0.6483(3) 0.33382(9) 0.25677(9) 0.0172(3) Uani 1 1 d . . . H1 H 0.7596 0.3672 0.3122 0.021 Uiso 1 1 calc R . . C2 C 0.6826(3) 0.36077(9) 0.15840(9) 0.0166(3) Uani 1 1 d . . . H2 H 0.8106 0.4110 0.1491 0.020 Uiso 1 1 calc R . . C3 C 0.5285(3) 0.31360(8) 0.07426(9) 0.0141(3) Uani 1 1 d . . . C4 C 0.3342(3) 0.23931(8) 0.09471(9) 0.0138(2) Uani 1 1 d . . . C5 C 0.1584(3) 0.18721(9) 0.01650(9) 0.0160(3) Uani 1 1 d . . . H5 H 0.1684 0.2005 -0.0529 0.019 Uiso 1 1 calc R . . C6 C -0.0266(3) 0.11784(9) 0.03904(9) 0.0169(3) Uani 1 1 d . . . H6 H -0.1461 0.0839 -0.0140 0.020 Uiso 1 1 calc R . . C7 C -0.0360(3) 0.09789(9) 0.14211(10) 0.0159(3) Uani 1 1 d . . . C8 C 0.1290(3) 0.14623(9) 0.22017(9) 0.0161(3) Uani 1 1 d . . . H8 H 0.1177 0.1312 0.2890 0.019 Uiso 1 1 calc R . . C9 C 0.3172(3) 0.21895(9) 0.19809(9) 0.0147(3) Uani 1 1 d . . . C10 C 0.7517(3) 0.40802(9) -0.04607(10) 0.0181(3) Uani 1 1 d . . . H10A H 0.7147 0.4681 -0.0136 0.027 Uiso 1 1 calc R . . H10B H 0.7277 0.4170 -0.1202 0.027 Uiso 1 1 calc R . . H10C H 0.9501 0.3870 -0.0198 0.027 Uiso 1 1 calc R . . 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 0.0197(2) 0.01813(18) 0.02085(19) 0.00144(11) 0.00710(13) -0.00236(11) N1 0.0192(5) 0.0196(5) 0.0117(5) -0.0006(4) 0.0024(4) 0.0019(4) N2 0.0180(5) 0.0170(5) 0.0132(5) -0.0004(4) 0.0037(4) -0.0023(4) C1 0.0183(6) 0.0191(6) 0.0138(6) -0.0033(5) 0.0010(5) 0.0018(5) C2 0.0171(6) 0.0164(6) 0.0166(6) -0.0009(5) 0.0035(5) -0.0002(5) C3 0.0135(6) 0.0149(6) 0.0143(6) 0.0008(4) 0.0034(4) 0.0041(4) C4 0.0133(6) 0.0149(6) 0.0134(6) 0.0002(4) 0.0029(4) 0.0028(4) C5 0.0188(6) 0.0180(6) 0.0113(5) 0.0008(4) 0.0031(4) 0.0017(5) C6 0.0181(6) 0.0173(6) 0.0148(6) -0.0018(5) 0.0012(5) -0.0002(5) C7 0.0153(6) 0.0145(6) 0.0188(6) 0.0023(5) 0.0058(5) 0.0019(4) C8 0.0176(6) 0.0182(6) 0.0135(6) 0.0025(5) 0.0054(5) 0.0038(5) C9 0.0150(6) 0.0163(6) 0.0130(5) 0.0002(4) 0.0030(4) 0.0047(5) C10 0.0175(6) 0.0191(6) 0.0186(6) 0.0023(5) 0.0058(5) -0.0008(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 Cl1 C7 1.7443(13) . ? N1 C1 1.3249(17) . ? N1 C9 1.3734(16) . ? N2 C3 1.3564(16) . ? N2 C10 1.4515(16) . ? N2 H2N 0.8799 . ? C1 C2 1.3977(17) . ? C1 H1 0.9500 . ? C2 C3 1.3910(18) . ? C2 H2 0.9500 . ? C3 C4 1.4433(17) . ? C4 C5 1.4150(17) . ? C4 C9 1.4198(17) . ? C5 C6 1.3731(18) . ? C5 H5 0.9500 . ? C6 C7 1.4071(17) . ? C6 H6 0.9500 . ? C7 C8 1.3640(18) . ? C8 C9 1.4152(18) . ? C8 H8 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 C9 115.61(11) . . ? C3 N2 C10 121.45(10) . . ? C3 N2 H2N 120.2 . . ? C10 N2 H2N 114.0 . . ? N1 C1 C2 125.96(12) . . ? N1 C1 H1 117.0 . . ? C2 C1 H1 117.0 . . ? C3 C2 C1 119.66(12) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? N2 C3 C2 122.84(12) . . ? N2 C3 C4 120.29(11) . . ? C2 C3 C4 116.84(11) . . ? C5 C4 C9 118.91(11) . . ? C5 C4 C3 122.94(11) . . ? C9 C4 C3 118.15(11) . . ? C6 C5 C4 121.19(11) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 118.82(11) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C8 C7 C6 122.15(12) . . ? C8 C7 Cl1 119.54(10) . . ? C6 C7 Cl1 118.30(10) . . ? C7 C8 C9 119.66(11) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? N1 C9 C8 116.98(11) . . ? N1 C9 C4 123.78(11) . . ? C8 C9 C4 119.25(11) . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 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 C9 N1 C1 C2 0.17(18) . . . . ? N1 C1 C2 C3 -0.9(2) . . . . ? C10 N2 C3 C2 5.26(18) . . . . ? C10 N2 C3 C4 -176.96(10) . . . . ? C1 C2 C3 N2 179.04(11) . . . . ? C1 C2 C3 C4 1.19(17) . . . . ? N2 C3 C4 C5 0.37(18) . . . . ? C2 C3 C4 C5 178.28(12) . . . . ? N2 C3 C4 C9 -178.73(11) . . . . ? C2 C3 C4 C9 -0.83(17) . . . . ? C9 C4 C5 C6 -0.05(18) . . . . ? C3 C4 C5 C6 -179.15(11) . . . . ? C4 C5 C6 C7 -1.00(18) . . . . ? C5 C6 C7 C8 1.09(19) . . . . ? C5 C6 C7 Cl1 -177.99(9) . . . . ? C6 C7 C8 C9 -0.08(19) . . . . ? Cl1 C7 C8 C9 178.99(9) . . . . ? C1 N1 C9 C8 -179.85(11) . . . . ? C1 N1 C9 C4 0.22(17) . . . . ? C7 C8 C9 N1 179.07(11) . . . . ? C7 C8 C9 C4 -0.99(18) . . . . ? C5 C4 C9 N1 -179.01(11) . . . . ? C3 C4 C9 N1 0.13(18) . . . . ? C5 C4 C9 C8 1.05(17) . . . . ? C3 C4 C9 C8 -179.80(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.31 _refine_diff_density_min -0.22 _refine_diff_density_rms 0.048 # Attachment '2_nPr.CIF' data_nPr _database_code_depnum_ccdc_archive 'CCDC 697892' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 Cl N2' _chemical_formula_sum 'C12 H13 Cl N2' _chemical_formula_weight 220.69 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/c' _symmetry_space_group_name_Hall '-P 2ybc ' 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 10.4386(3) _cell_length_b 17.9769(5) _cell_length_c 13.0512(3) _cell_angle_alpha 90 _cell_angle_beta 108.987(2) _cell_angle_gamma 90 _cell_volume 2315.85(11) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5401 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description rod _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.298 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.747 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 33628 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_av_sigmaI/netI 0.039 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 27.5 _reflns_number_total 5297 _reflns_number_gt 3930 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006' _computing_publication_material SHELXL97 _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^)+(0.1031P)^2^+1.6308P] 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 5297 _refine_ls_number_parameters 277 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.086 _refine_ls_R_factor_gt 0.059 _refine_ls_wR_factor_ref 0.189 _refine_ls_wR_factor_gt 0.165 _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_restrained_S_all 1.07 _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 0.92021(7) 0.46245(4) 0.60977(6) 0.0384(2) Uani 1 1 d . . . Cl1A Cl 0.76025(7) 0.01571(4) 0.63660(7) 0.0425(2) Uani 1 1 d . . . N1 N 0.6077(2) 0.25218(13) 0.42238(15) 0.0267(5) Uani 1 1 d . . . N2 N 0.5607(2) 0.17474(11) 0.71318(16) 0.0235(4) Uani 1 1 d D . . H2N H 0.5872 0.2016 0.7727 0.028 Uiso 1 1 d D . . N1A N 1.0547(2) 0.22809(12) 0.84096(15) 0.0267(5) Uani 1 1 d . . . N2A N 1.1180(2) 0.31452(12) 0.56132(16) 0.0266(5) Uani 1 1 d D . . H2NA H 1.0810 0.2949 0.4967 0.032 Uiso 1 1 d D . . C1 C 0.5346(3) 0.19270(15) 0.42721(19) 0.0279(6) Uani 1 1 d . . . H1 H 0.4924 0.1670 0.3612 0.033 Uiso 1 1 calc R . . C2 C 0.5137(2) 0.16440(14) 0.51944(19) 0.0256(5) Uani 1 1 d . . . H2 H 0.4587 0.1216 0.5148 0.031 Uiso 1 1 calc R . . C3 C 0.5743(2) 0.19934(13) 0.61914(17) 0.0196(5) Uani 1 1 d . . . C4 C 0.6569(2) 0.26374(13) 0.61910(17) 0.0183(5) Uani 1 1 d . . . C5 C 0.7278(2) 0.30324(13) 0.71453(18) 0.0202(5) Uani 1 1 d . . . H5 H 0.7202 0.2877 0.7819 0.024 Uiso 1 1 calc R . . C6 C 0.8073(2) 0.36364(13) 0.71175(19) 0.0241(5) Uani 1 1 d . . . H6 H 0.8544 0.3896 0.7764 0.029 Uiso 1 1 calc R . . C7 C 0.8180(2) 0.38641(13) 0.6117(2) 0.0244(5) Uani 1 1 d . . . C8 C 0.7514(2) 0.35017(14) 0.5177(2) 0.0252(5) Uani 1 1 d . . . H8 H 0.7597 0.3669 0.4511 0.030 Uiso 1 1 calc R . . C9 C 0.6698(2) 0.28768(13) 0.51911(18) 0.0207(5) Uani 1 1 d . . . C10 C 0.4800(2) 0.11040(14) 0.7210(2) 0.0258(5) Uani 1 1 d . . . H10A H 0.5136 0.0912 0.7962 0.031 Uiso 1 1 calc R . . H10B H 0.4937 0.0709 0.6728 0.031 Uiso 1 1 calc R . . C11 C 0.3288(3) 0.12589(15) 0.6912(2) 0.0307(6) Uani 1 1 d . . . H11A H 0.3134 0.1635 0.7414 0.037 Uiso 1 1 calc R . . H11B H 0.2944 0.1464 0.6168 0.037 Uiso 1 1 calc R . . C12 C 0.2515(3) 0.05510(17) 0.6974(3) 0.0428(7) Uani 1 1 d . . . H12A H 0.1544 0.0661 0.6761 0.064 Uiso 1 1 calc R . . H12B H 0.2829 0.0360 0.7718 0.064 Uiso 1 1 calc R . . H12C H 0.2676 0.0177 0.6484 0.064 Uiso 1 1 calc R . . C1A C 1.1331(3) 0.28631(15) 0.84294(19) 0.0274(5) Uani 1 1 d . . . H1A H 1.1748 0.3093 0.9113 0.033 Uiso 1 1 calc R . . C2A C 1.1602(2) 0.31701(14) 0.75402(18) 0.0236(5) Uani 1 1 d . . . H2A H 1.2191 0.3586 0.7632 0.028 Uiso 1 1 calc R . . C3A C 1.0998(2) 0.28609(13) 0.65108(17) 0.0194(5) Uani 1 1 d . . . C4A C 1.0152(2) 0.22172(13) 0.64481(17) 0.0185(5) Uani 1 1 d . . . C5A C 0.9495(2) 0.18378(13) 0.54661(18) 0.0223(5) Uani 1 1 d . . . H5A H 0.9592 0.2017 0.4811 0.027 Uiso 1 1 calc R . . C6A C 0.8719(3) 0.12146(14) 0.5441(2) 0.0268(5) Uani 1 1 d . . . H6A H 0.8289 0.0964 0.4777 0.032 Uiso 1 1 calc R . . C7A C 0.8574(2) 0.09563(13) 0.6412(2) 0.0269(5) Uani 1 1 d . . . C8A C 0.9163(2) 0.13082(14) 0.7375(2) 0.0256(5) Uani 1 1 d . . . H8A H 0.9035 0.1124 0.8017 0.031 Uiso 1 1 calc R . . C9A C 0.9968(2) 0.19528(13) 0.74170(18) 0.0214(5) Uani 1 1 d . . . C10A C 1.2039(3) 0.37756(15) 0.5600(2) 0.0346(6) Uani 1 1 d . . . H10C H 1.1980 0.4138 0.6154 0.041 Uiso 1 1 calc R . . H10D H 1.1689 0.4022 0.4885 0.041 Uiso 1 1 calc R . . C11A C 1.3482(3) 0.35800(16) 0.5811(2) 0.0368(6) Uani 1 1 d . . . H11C H 1.3554 0.3215 0.5264 0.044 Uiso 1 1 calc R . . H11D H 1.3851 0.3347 0.6535 0.044 Uiso 1 1 calc R . . C12A C 1.4311(3) 0.42739(18) 0.5763(4) 0.0636(11) Uani 1 1 d . . . H12D H 1.5263 0.4135 0.5917 0.095 Uiso 1 1 calc R . . H12E H 1.4238 0.4635 0.6303 0.095 Uiso 1 1 calc R . . H12F H 1.3964 0.4495 0.5039 0.095 Uiso 1 1 calc R . . 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 0.0319(4) 0.0238(3) 0.0618(5) 0.0091(3) 0.0183(3) -0.0037(3) Cl1A 0.0389(4) 0.0254(4) 0.0636(5) 0.0084(3) 0.0174(4) -0.0072(3) N1 0.0238(11) 0.0393(13) 0.0166(9) 0.0014(8) 0.0061(8) 0.0014(9) N2 0.0295(11) 0.0245(11) 0.0190(9) -0.0013(8) 0.0115(8) -0.0056(9) N1A 0.0271(11) 0.0368(12) 0.0162(9) 0.0028(8) 0.0072(8) 0.0042(9) N2A 0.0413(13) 0.0222(11) 0.0201(10) -0.0032(8) 0.0150(9) -0.0082(9) C1 0.0261(13) 0.0390(15) 0.0163(11) -0.0045(10) 0.0039(10) -0.0019(11) C2 0.0236(12) 0.0299(13) 0.0226(12) -0.0044(10) 0.0068(9) -0.0043(10) C3 0.0192(11) 0.0226(12) 0.0177(11) 0.0002(9) 0.0070(9) 0.0021(9) C4 0.0177(11) 0.0209(11) 0.0168(10) 0.0015(8) 0.0065(8) 0.0021(9) C5 0.0212(11) 0.0215(11) 0.0185(11) 0.0003(9) 0.0071(9) 0.0008(9) C6 0.0222(12) 0.0209(12) 0.0272(12) -0.0027(9) 0.0052(10) 0.0014(9) C7 0.0193(12) 0.0184(11) 0.0367(13) 0.0072(10) 0.0109(10) 0.0009(9) C8 0.0227(12) 0.0282(13) 0.0270(12) 0.0115(10) 0.0112(10) 0.0065(10) C9 0.0185(11) 0.0259(12) 0.0183(11) 0.0046(9) 0.0069(9) 0.0041(9) C10 0.0287(13) 0.0227(12) 0.0280(12) 0.0033(10) 0.0121(10) -0.0021(10) C11 0.0306(14) 0.0290(14) 0.0342(14) 0.0046(11) 0.0130(11) -0.0007(11) C12 0.0297(15) 0.0354(16) 0.066(2) 0.0030(14) 0.0189(14) -0.0062(12) C1A 0.0254(13) 0.0388(15) 0.0160(11) -0.0044(10) 0.0039(9) 0.0014(11) C2A 0.0218(12) 0.0259(12) 0.0226(12) -0.0048(9) 0.0065(9) -0.0026(9) C3A 0.0202(11) 0.0210(11) 0.0179(11) -0.0004(8) 0.0074(9) 0.0019(9) C4A 0.0184(11) 0.0203(11) 0.0170(10) 0.0018(8) 0.0060(9) 0.0027(9) C5A 0.0257(12) 0.0221(12) 0.0193(11) -0.0010(9) 0.0075(9) -0.0013(9) C6A 0.0274(13) 0.0231(12) 0.0275(12) -0.0020(10) 0.0056(10) -0.0022(10) C7A 0.0229(12) 0.0193(12) 0.0403(14) 0.0056(10) 0.0129(11) 0.0004(9) C8A 0.0249(13) 0.0268(13) 0.0273(12) 0.0092(10) 0.0118(10) 0.0056(10) C9A 0.0209(12) 0.0248(12) 0.0192(11) 0.0058(9) 0.0076(9) 0.0060(9) C10A 0.0459(17) 0.0262(13) 0.0389(15) -0.0044(11) 0.0239(13) -0.0106(12) C11A 0.0377(16) 0.0308(15) 0.0412(15) 0.0030(12) 0.0118(12) 0.0014(12) C12A 0.0278(16) 0.0317(17) 0.131(4) 0.000(2) 0.026(2) -0.0038(13) _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 C7 1.739(2) . ? Cl1A C7A 1.748(2) . ? N1 C1 1.327(3) . ? N1 C9 1.374(3) . ? N2 C3 1.355(3) . ? N2 C10 1.453(3) . ? N2 H2N 0.8800 . ? N1A C1A 1.324(3) . ? N1A C9A 1.372(3) . ? N2A C3A 1.347(3) . ? N2A C10A 1.448(3) . ? N2A H2NA 0.8800 . ? C1 C2 1.388(3) . ? C1 H1 0.9500 . ? C2 C3 1.397(3) . ? C2 H2 0.9500 . ? C3 C4 1.443(3) . ? C4 C5 1.415(3) . ? C4 C9 1.422(3) . ? C5 C6 1.375(3) . ? C5 H5 0.9500 . ? C6 C7 1.407(3) . ? C6 H6 0.9500 . ? C7 C8 1.363(4) . ? C8 C9 1.413(3) . ? C8 H8 0.9500 . ? C10 C11 1.524(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.523(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C1A C2A 1.394(3) . ? C1A H1A 0.9500 . ? C2A C3A 1.400(3) . ? C2A H2A 0.9500 . ? C3A C4A 1.442(3) . ? C4A C5A 1.416(3) . ? C4A C9A 1.421(3) . ? C5A C6A 1.376(3) . ? C5A H5A 0.9500 . ? C6A C7A 1.403(4) . ? C6A H6A 0.9500 . ? C7A C8A 1.362(4) . ? C8A C9A 1.422(3) . ? C8A H8A 0.9500 . ? C10A C11A 1.483(4) . ? C10A H10C 0.9900 . ? C10A H10D 0.9900 . ? C11A C12A 1.531(4) . ? C11A H11C 0.9900 . ? C11A H11D 0.9900 . ? C12A H12D 0.9800 . ? C12A H12E 0.9800 . ? C12A H12F 0.9800 . ? 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 C9 115.92(19) . . ? C3 N2 C10 123.9(2) . . ? C3 N2 H2N 121.7 . . ? C10 N2 H2N 113.4 . . ? C1A N1A C9A 115.97(19) . . ? C3A N2A C10A 124.8(2) . . ? C3A N2A H2NA 122.6 . . ? C10A N2A H2NA 112.6 . . ? N1 C1 C2 126.3(2) . . ? N1 C1 H1 116.9 . . ? C2 C1 H1 116.9 . . ? C1 C2 C3 119.5(2) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? N2 C3 C2 123.2(2) . . ? N2 C3 C4 120.1(2) . . ? C2 C3 C4 116.7(2) . . ? C5 C4 C9 118.5(2) . . ? C5 C4 C3 122.91(19) . . ? C9 C4 C3 118.6(2) . . ? C6 C5 C4 121.4(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 119.0(2) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C8 C7 C6 121.7(2) . . ? C8 C7 Cl1 119.90(18) . . ? C6 C7 Cl1 118.42(19) . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? N1 C9 C8 117.6(2) . . ? N1 C9 C4 123.0(2) . . ? C8 C9 C4 119.4(2) . . ? N2 C10 C11 114.3(2) . . ? N2 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? N2 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 110.9(2) . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1A C1A C2A 126.0(2) . . ? N1A C1A H1A 117.0 . . ? C2A C1A H1A 117.0 . . ? C1A C2A C3A 119.4(2) . . ? C1A C2A H2A 120.3 . . ? C3A C2A H2A 120.3 . . ? N2A C3A C2A 122.5(2) . . ? N2A C3A C4A 120.8(2) . . ? C2A C3A C4A 116.7(2) . . ? C5A C4A C9A 118.6(2) . . ? C5A C4A C3A 123.03(19) . . ? C9A C4A C3A 118.4(2) . . ? C6A C5A C4A 121.4(2) . . ? C6A C5A H5A 119.3 . . ? C4A C5A H5A 119.3 . . ? C5A C6A C7A 118.9(2) . . ? C5A C6A H6A 120.5 . . ? C7A C6A H6A 120.5 . . ? C8A C7A C6A 122.1(2) . . ? C8A C7A Cl1A 119.71(19) . . ? C6A C7A Cl1A 118.2(2) . . ? C7A C8A C9A 119.8(2) . . ? C7A C8A H8A 120.1 . . ? C9A C8A H8A 120.1 . . ? N1A C9A C4A 123.4(2) . . ? N1A C9A C8A 117.4(2) . . ? C4A C9A C8A 119.2(2) . . ? N2A C10A C11A 114.0(2) . . ? N2A C10A H10C 108.7 . . ? C11A C10A H10C 108.7 . . ? N2A C10A H10D 108.7 . . ? C11A C10A H10D 108.7 . . ? H10C C10A H10D 107.6 . . ? C10A C11A C12A 110.7(2) . . ? C10A C11A H11C 109.5 . . ? C12A C11A H11C 109.5 . . ? C10A C11A H11D 109.5 . . ? C12A C11A H11D 109.5 . . ? H11C C11A H11D 108.1 . . ? C11A C12A H12D 109.5 . . ? C11A C12A H12E 109.5 . . ? H12D C12A H12E 109.5 . . ? C11A C12A H12F 109.5 . . ? H12D C12A H12F 109.5 . . ? H12E C12A H12F 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 C9 N1 C1 C2 1.1(4) . . . . ? N1 C1 C2 C3 -0.7(4) . . . . ? C10 N2 C3 C2 -1.1(4) . . . . ? C10 N2 C3 C4 -179.8(2) . . . . ? C1 C2 C3 N2 -179.1(2) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? N2 C3 C4 C5 0.8(3) . . . . ? C2 C3 C4 C5 -178.0(2) . . . . ? N2 C3 C4 C9 179.5(2) . . . . ? C2 C3 C4 C9 0.7(3) . . . . ? C9 C4 C5 C6 0.2(3) . . . . ? C3 C4 C5 C6 178.9(2) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? C5 C6 C7 C8 0.1(4) . . . . ? C5 C6 C7 Cl1 -179.47(18) . . . . ? C6 C7 C8 C9 -0.5(4) . . . . ? Cl1 C7 C8 C9 179.05(17) . . . . ? C1 N1 C9 C8 178.5(2) . . . . ? C1 N1 C9 C4 -0.7(3) . . . . ? C7 C8 C9 N1 -178.4(2) . . . . ? C7 C8 C9 C4 0.8(3) . . . . ? C5 C4 C9 N1 178.5(2) . . . . ? C3 C4 C9 N1 -0.2(3) . . . . ? C5 C4 C9 C8 -0.6(3) . . . . ? C3 C4 C9 C8 -179.4(2) . . . . ? C3 N2 C10 C11 -81.3(3) . . . . ? N2 C10 C11 C12 177.8(2) . . . . ? C9A N1A C1A C2A 0.7(4) . . . . ? N1A C1A C2A C3A 1.0(4) . . . . ? C10A N2A C3A C2A 2.1(4) . . . . ? C10A N2A C3A C4A -178.2(2) . . . . ? C1A C2A C3A N2A 177.8(2) . . . . ? C1A C2A C3A C4A -1.9(3) . . . . ? N2A C3A C4A C5A 1.5(3) . . . . ? C2A C3A C4A C5A -178.8(2) . . . . ? N2A C3A C4A C9A -178.4(2) . . . . ? C2A C3A C4A C9A 1.2(3) . . . . ? C9A C4A C5A C6A -1.6(3) . . . . ? C3A C4A C5A C6A 178.5(2) . . . . ? C4A C5A C6A C7A 0.4(4) . . . . ? C5A C6A C7A C8A 0.8(4) . . . . ? C5A C6A C7A Cl1A -179.20(19) . . . . ? C6A C7A C8A C9A -0.9(4) . . . . ? Cl1A C7A C8A C9A 179.17(18) . . . . ? C1A N1A C9A C4A -1.4(3) . . . . ? C1A N1A C9A C8A 177.6(2) . . . . ? C5A C4A C9A N1A -179.5(2) . . . . ? C3A C4A C9A N1A 0.4(3) . . . . ? C5A C4A C9A C8A 1.5(3) . . . . ? C3A C4A C9A C8A -178.6(2) . . . . ? C7A C8A C9A N1A -179.4(2) . . . . ? C7A C8A C9A C4A -0.3(3) . . . . ? C3A N2A C10A C11A 85.4(3) . . . . ? N2A C10A C11A C12A 179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.31 # 1.02 A from atom H11c _refine_diff_density_min -0.50 # 0.70 A from atom C11a _refine_diff_density_rms 0.164 # Attachment '3_nBu.CIF' data_nBu _database_code_depnum_ccdc_archive 'CCDC 697893' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 Cl N2' _chemical_formula_sum 'C13 H15 Cl N2' _chemical_formula_weight 234.72 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 9.3167(3) _cell_length_b 20.4346(11) _cell_length_c 25.3335(15) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4823.1(4) _cell_formula_units_Z 16 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5750 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 0.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.653 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 31816 _diffrn_reflns_av_R_equivalents 0.097 _diffrn_reflns_av_sigmaI/netI 0.082 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 27.5 _reflns_number_total 5448 _reflns_number_gt 3365 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006' _computing_publication_material SHELXL97 _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^)+(0.0781P)^2^] 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 5448 _refine_ls_number_parameters 295 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.110 _refine_ls_R_factor_gt 0.055 _refine_ls_wR_factor_ref 0.156 _refine_ls_wR_factor_gt 0.128 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _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 0.98938(7) -0.18702(3) 0.77435(3) 0.0307(2) Uani 1 1 d . . . Cl1A Cl 0.48122(7) -0.17364(3) 0.54392(3) 0.0326(2) Uani 1 1 d . . . N1 N 0.6452(2) -0.03163(10) 0.86693(8) 0.0239(5) Uani 1 1 d . . . N2 N 0.5363(2) 0.06703(11) 0.72614(9) 0.0227(5) Uani 1 1 d D . . H2N H 0.5660 0.0505 0.6960 0.027 Uiso 1 1 d D . . N1A N 0.6538(2) 0.04462(11) 0.61510(9) 0.0240(5) Uani 1 1 d . . . N2A N 0.8688(2) 0.09558(10) 0.47411(9) 0.0239(5) Uani 1 1 d D . . H2NA H 0.8549 0.0736 0.4447 0.029 Uiso 1 1 d D . . C1 C 0.5576(3) 0.01927(13) 0.86513(10) 0.0244(6) Uani 1 1 d . . . H1 H 0.5157 0.0329 0.8975 0.029 Uiso 1 1 calc R . . C2 C 0.5211(2) 0.05460(13) 0.82036(10) 0.0227(6) Uani 1 1 d . . . H2 H 0.4598 0.0916 0.8232 0.027 Uiso 1 1 calc R . . C3 C 0.5743(3) 0.03592(12) 0.77137(10) 0.0190(6) Uani 1 1 d . . . C4 C 0.6742(2) -0.01822(12) 0.77096(10) 0.0199(6) Uani 1 1 d . . . C5 C 0.7443(2) -0.03995(12) 0.72459(10) 0.0203(6) Uani 1 1 d . . . H5 H 0.7244 -0.0189 0.6920 0.024 Uiso 1 1 calc R . . C6 C 0.8401(3) -0.09070(12) 0.72587(11) 0.0230(6) Uani 1 1 d . . . H6 H 0.8880 -0.1042 0.6946 0.028 Uiso 1 1 calc R . . C7 C 0.8668(2) -0.12240(12) 0.77392(11) 0.0226(6) Uani 1 1 d . . . C8 C 0.8011(3) -0.10355(12) 0.81983(11) 0.0229(6) Uani 1 1 d . . . H8 H 0.8200 -0.1264 0.8517 0.027 Uiso 1 1 calc R . . C9 C 0.7051(2) -0.04996(12) 0.81956(10) 0.0205(6) Uani 1 1 d . . . C10 C 0.4301(3) 0.11959(12) 0.72627(10) 0.0231(6) Uani 1 1 d . . . H10A H 0.4723 0.1588 0.7431 0.028 Uiso 1 1 calc R . . H10B H 0.3463 0.1059 0.7476 0.028 Uiso 1 1 calc R . . C11 C 0.3798(3) 0.13720(13) 0.67114(10) 0.0245(6) Uani 1 1 d . . . H11A H 0.3381 0.0980 0.6540 0.029 Uiso 1 1 calc R . . H11B H 0.4628 0.1518 0.6498 0.029 Uiso 1 1 calc R . . C12 C 0.2677(3) 0.19149(13) 0.67295(11) 0.0286(7) Uani 1 1 d . . . H12A H 0.1903 0.1787 0.6976 0.034 Uiso 1 1 calc R . . H12B H 0.3129 0.2318 0.6869 0.034 Uiso 1 1 calc R . . C13 C 0.2023(3) 0.20610(15) 0.61923(12) 0.0384(8) Uani 1 1 d . . . H13A H 0.1310 0.2411 0.6228 0.058 Uiso 1 1 calc R . . H13B H 0.1558 0.1666 0.6055 0.058 Uiso 1 1 calc R . . H13C H 0.2779 0.2200 0.5948 0.058 Uiso 1 1 calc R . . C1A C 0.7231(3) 0.10060(13) 0.60808(11) 0.0246(6) Uani 1 1 d . . . H1A H 0.7233 0.1303 0.6369 0.029 Uiso 1 1 calc R . . C2A C 0.7956(3) 0.12029(13) 0.56281(10) 0.0226(6) Uani 1 1 d . . . H2A H 0.8435 0.1613 0.5618 0.027 Uiso 1 1 calc R . . C3A C 0.7973(3) 0.07891(13) 0.51872(10) 0.0214(6) Uani 1 1 d . . . C4A C 0.7216(2) 0.01780(13) 0.52357(10) 0.0209(6) Uani 1 1 d . . . C5A C 0.7104(3) -0.02829(13) 0.48192(11) 0.0252(6) Uani 1 1 d . . . H5A H 0.7542 -0.0189 0.4489 0.030 Uiso 1 1 calc R . . C6A C 0.6381(3) -0.08576(13) 0.48816(11) 0.0284(6) Uani 1 1 d . . . H6A H 0.6307 -0.1159 0.4597 0.034 Uiso 1 1 calc R . . C7A C 0.5747(3) -0.09995(13) 0.53714(11) 0.0248(6) Uani 1 1 d . . . C8A C 0.5822(3) -0.05743(13) 0.57846(11) 0.0253(6) Uani 1 1 d . . . H8A H 0.5387 -0.0683 0.6112 0.030 Uiso 1 1 calc R . . C9A C 0.6548(2) 0.00279(12) 0.57247(11) 0.0222(6) Uani 1 1 d . . . C10A C 0.9516(3) 0.15597(13) 0.47050(11) 0.0256(6) Uani 1 1 d . . . H10C H 1.0192 0.1584 0.5006 0.031 Uiso 1 1 calc R . . H10D H 0.8858 0.1939 0.4728 0.031 Uiso 1 1 calc R . . C11A C 1.0355(3) 0.15952(13) 0.41896(11) 0.0251(6) Uani 1 1 d . . . H11C H 1.0932 0.1192 0.4148 0.030 Uiso 1 1 calc R . . H11D H 0.9674 0.1620 0.3890 0.030 Uiso 1 1 calc R . . C12A C 1.1344(3) 0.21879(13) 0.41763(11) 0.0279(6) Uani 1 1 d . . . H12C H 1.0761 0.2591 0.4208 0.033 Uiso 1 1 calc R . . H12D H 1.2001 0.2170 0.4483 0.033 Uiso 1 1 calc R . . C13A C 1.2226(3) 0.22211(14) 0.36712(11) 0.0323(7) Uani 1 1 d . . . H13D H 1.2839 0.2611 0.3679 0.048 Uiso 1 1 calc R . . H13E H 1.1581 0.2245 0.3366 0.048 Uiso 1 1 calc R . . H13F H 1.2827 0.1829 0.3643 0.048 Uiso 1 1 calc R . . 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 0.0298(4) 0.0278(4) 0.0345(4) 0.0022(3) -0.0021(3) 0.0061(3) Cl1A 0.0369(4) 0.0309(4) 0.0301(4) 0.0033(3) 0.0025(3) -0.0078(3) N1 0.0293(12) 0.0283(13) 0.0143(12) 0.0019(9) -0.0011(10) -0.0017(10) N2 0.0261(11) 0.0261(13) 0.0160(13) 0.0017(10) 0.0015(10) 0.0046(9) N1A 0.0281(12) 0.0288(13) 0.0151(13) 0.0017(10) 0.0014(9) 0.0024(10) N2A 0.0318(12) 0.0257(13) 0.0142(13) -0.0010(9) 0.0037(10) -0.0035(10) C1 0.0290(14) 0.0297(16) 0.0144(15) -0.0044(11) 0.0024(12) -0.0017(12) C2 0.0243(13) 0.0255(15) 0.0184(15) -0.0011(11) 0.0021(11) -0.0003(11) C3 0.0215(12) 0.0188(14) 0.0165(14) 0.0019(11) -0.0025(11) -0.0048(10) C4 0.0193(12) 0.0233(14) 0.0171(15) -0.0003(11) -0.0002(11) -0.0046(10) C5 0.0199(12) 0.0242(14) 0.0167(14) 0.0015(11) -0.0020(11) -0.0033(10) C6 0.0239(13) 0.0250(15) 0.0202(16) -0.0008(11) 0.0010(11) -0.0022(11) C7 0.0214(13) 0.0246(15) 0.0219(16) 0.0021(11) -0.0033(11) 0.0006(11) C8 0.0245(13) 0.0247(15) 0.0195(16) 0.0056(11) -0.0056(11) -0.0047(11) C9 0.0207(12) 0.0252(15) 0.0157(15) -0.0001(11) -0.0002(11) -0.0038(11) C10 0.0260(13) 0.0226(15) 0.0207(15) 0.0006(11) -0.0028(11) 0.0026(11) C11 0.0242(13) 0.0289(15) 0.0204(16) 0.0042(12) 0.0016(11) 0.0009(11) C12 0.0303(14) 0.0288(17) 0.0267(17) 0.0018(12) -0.0016(12) 0.0046(11) C13 0.0404(17) 0.0424(19) 0.0323(19) 0.0093(15) -0.0025(14) 0.0122(14) C1A 0.0266(14) 0.0291(16) 0.0180(16) -0.0021(12) -0.0027(12) 0.0054(11) C2A 0.0253(13) 0.0288(15) 0.0136(15) 0.0014(11) 0.0006(11) 0.0009(11) C3A 0.0223(13) 0.0266(15) 0.0155(15) 0.0031(11) -0.0001(11) 0.0051(11) C4A 0.0218(13) 0.0263(15) 0.0145(15) 0.0015(11) 0.0019(11) 0.0049(11) C5A 0.0317(15) 0.0272(16) 0.0168(15) 0.0021(12) 0.0038(12) 0.0005(12) C6A 0.0365(15) 0.0264(15) 0.0222(17) -0.0022(12) 0.0018(13) -0.0011(12) C7A 0.0241(13) 0.0276(16) 0.0226(16) 0.0065(12) -0.0005(12) -0.0022(11) C8A 0.0240(13) 0.0353(17) 0.0165(15) 0.0072(12) 0.0040(11) 0.0007(11) C9A 0.0217(13) 0.0277(15) 0.0171(15) 0.0029(11) -0.0018(11) 0.0051(11) C10A 0.0309(14) 0.0264(16) 0.0196(16) 0.0013(12) 0.0028(12) -0.0032(12) C11A 0.0301(14) 0.0264(15) 0.0189(15) -0.0011(12) 0.0027(12) -0.0027(11) C12A 0.0296(14) 0.0277(16) 0.0265(17) -0.0027(12) 0.0042(12) -0.0032(12) C13A 0.0379(16) 0.0318(17) 0.0272(18) -0.0017(13) 0.0063(13) -0.0071(13) _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 C7 1.746(2) . ? Cl1A C7A 1.748(3) . ? N1 C1 1.323(3) . ? N1 C9 1.375(3) . ? N2 C3 1.357(3) . ? N2 C10 1.460(3) . ? N2 H2N 0.8800 . ? N1A C1A 1.326(3) . ? N1A C9A 1.377(3) . ? N2A C3A 1.355(3) . ? N2A C10A 1.458(3) . ? N2A H2NA 0.8800 . ? C1 C2 1.387(4) . ? C1 H1 0.9500 . ? C2 C3 1.390(3) . ? C2 H2 0.9500 . ? C3 C4 1.446(3) . ? C4 C5 1.415(3) . ? C4 C9 1.421(3) . ? C5 C6 1.369(3) . ? C5 H5 0.9500 . ? C6 C7 1.401(3) . ? C6 H6 0.9500 . ? C7 C8 1.369(4) . ? C8 C9 1.414(3) . ? C8 H8 0.9500 . ? C10 C11 1.516(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.524(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.521(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C1A C2A 1.390(3) . ? C1A H1A 0.9500 . ? C2A C3A 1.401(4) . ? C2A H2A 0.9500 . ? C3A C4A 1.440(4) . ? C4A C5A 1.418(4) . ? C4A C9A 1.420(3) . ? C5A C6A 1.363(4) . ? C5A H5A 0.9500 . ? C6A C7A 1.405(4) . ? C6A H6A 0.9500 . ? C7A C8A 1.362(4) . ? C8A C9A 1.412(3) . ? C8A H8A 0.9500 . ? C10A C11A 1.523(4) . ? C10A H10C 0.9900 . ? C10A H10D 0.9900 . ? C11A C12A 1.523(3) . ? C11A H11C 0.9900 . ? C11A H11D 0.9900 . ? C12A C13A 1.522(4) . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? C13A H13D 0.9800 . ? C13A H13E 0.9800 . ? C13A H13F 0.9800 . ? 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 C9 115.8(2) . . ? C3 N2 C10 121.3(2) . . ? C3 N2 H2N 118.0 . . ? C10 N2 H2N 119.9 . . ? C1A N1A C9A 115.3(2) . . ? C3A N2A C10A 121.7(2) . . ? C3A N2A H2NA 120.4 . . ? C10A N2A H2NA 117.1 . . ? N1 C1 C2 126.0(2) . . ? N1 C1 H1 117.0 . . ? C2 C1 H1 117.0 . . ? C1 C2 C3 120.0(2) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? N2 C3 C2 122.2(2) . . ? N2 C3 C4 121.3(2) . . ? C2 C3 C4 116.5(2) . . ? C5 C4 C9 118.8(2) . . ? C5 C4 C3 122.9(2) . . ? C9 C4 C3 118.3(2) . . ? C6 C5 C4 121.3(2) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 119.1(2) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C8 C7 C6 121.9(2) . . ? C8 C7 Cl1 120.0(2) . . ? C6 C7 Cl1 118.1(2) . . ? C7 C8 C9 119.8(2) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? N1 C9 C8 117.6(2) . . ? N1 C9 C4 123.3(2) . . ? C8 C9 C4 119.1(2) . . ? N2 C10 C11 112.4(2) . . ? N2 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? N2 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 110.9(2) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C11 113.0(2) . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1A C1A C2A 126.6(3) . . ? N1A C1A H1A 116.7 . . ? C2A C1A H1A 116.7 . . ? C1A C2A C3A 119.2(2) . . ? C1A C2A H2A 120.4 . . ? C3A C2A H2A 120.4 . . ? N2A C3A C2A 121.2(2) . . ? N2A C3A C4A 122.0(2) . . ? C2A C3A C4A 116.7(2) . . ? C5A C4A C9A 118.3(2) . . ? C5A C4A C3A 123.3(2) . . ? C9A C4A C3A 118.5(2) . . ? C6A C5A C4A 121.5(2) . . ? C6A C5A H5A 119.3 . . ? C4A C5A H5A 119.3 . . ? C5A C6A C7A 119.2(3) . . ? C5A C6A H6A 120.4 . . ? C7A C6A H6A 120.4 . . ? C8A C7A C6A 121.7(2) . . ? C8A C7A Cl1A 120.0(2) . . ? C6A C7A Cl1A 118.3(2) . . ? C7A C8A C9A 119.9(2) . . ? C7A C8A H8A 120.1 . . ? C9A C8A H8A 120.1 . . ? N1A C9A C8A 117.0(2) . . ? N1A C9A C4A 123.6(2) . . ? C8A C9A C4A 119.5(2) . . ? N2A C10A C11A 111.4(2) . . ? N2A C10A H10C 109.3 . . ? C11A C10A H10C 109.3 . . ? N2A C10A H10D 109.3 . . ? C11A C10A H10D 109.3 . . ? H10C C10A H10D 108.0 . . ? C12A C11A C10A 111.6(2) . . ? C12A C11A H11C 109.3 . . ? C10A C11A H11C 109.3 . . ? C12A C11A H11D 109.3 . . ? C10A C11A H11D 109.3 . . ? H11C C11A H11D 108.0 . . ? C13A C12A C11A 112.4(2) . . ? C13A C12A H12C 109.1 . . ? C11A C12A H12C 109.1 . . ? C13A C12A H12D 109.1 . . ? C11A C12A H12D 109.1 . . ? H12C C12A H12D 107.9 . . ? C12A C13A H13D 109.5 . . ? C12A C13A H13E 109.5 . . ? H13D C13A H13E 109.5 . . ? C12A C13A H13F 109.5 . . ? H13D C13A H13F 109.5 . . ? H13E C13A H13F 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 C9 N1 C1 C2 0.4(4) . . . . ? N1 C1 C2 C3 2.4(4) . . . . ? C10 N2 C3 C2 -3.8(4) . . . . ? C10 N2 C3 C4 177.0(2) . . . . ? C1 C2 C3 N2 176.8(2) . . . . ? C1 C2 C3 C4 -3.9(3) . . . . ? N2 C3 C4 C5 3.5(4) . . . . ? C2 C3 C4 C5 -175.8(2) . . . . ? N2 C3 C4 C9 -177.8(2) . . . . ? C2 C3 C4 C9 2.9(3) . . . . ? C9 C4 C5 C6 0.2(4) . . . . ? C3 C4 C5 C6 178.9(2) . . . . ? C4 C5 C6 C7 1.3(4) . . . . ? C5 C6 C7 C8 -0.9(4) . . . . ? C5 C6 C7 Cl1 179.92(18) . . . . ? C6 C7 C8 C9 -1.0(4) . . . . ? Cl1 C7 C8 C9 178.15(18) . . . . ? C1 N1 C9 C8 179.1(2) . . . . ? C1 N1 C9 C4 -1.5(3) . . . . ? C7 C8 C9 N1 -178.0(2) . . . . ? C7 C8 C9 C4 2.5(4) . . . . ? C5 C4 C9 N1 178.5(2) . . . . ? C3 C4 C9 N1 -0.2(4) . . . . ? C5 C4 C9 C8 -2.1(3) . . . . ? C3 C4 C9 C8 179.2(2) . . . . ? C3 N2 C10 C11 -167.4(2) . . . . ? N2 C10 C11 C12 179.2(2) . . . . ? C10 C11 C12 C13 -174.0(2) . . . . ? C9A N1A C1A C2A -0.4(4) . . . . ? N1A C1A C2A C3A 0.9(4) . . . . ? C10A N2A C3A C2A 2.3(4) . . . . ? C10A N2A C3A C4A -176.7(2) . . . . ? C1A C2A C3A N2A -178.8(2) . . . . ? C1A C2A C3A C4A 0.3(3) . . . . ? N2A C3A C4A C5A -2.8(4) . . . . ? C2A C3A C4A C5A 178.2(2) . . . . ? N2A C3A C4A C9A 177.2(2) . . . . ? C2A C3A C4A C9A -1.8(3) . . . . ? C9A C4A C5A C6A -0.2(4) . . . . ? C3A C4A C5A C6A 179.7(2) . . . . ? C4A C5A C6A C7A -0.7(4) . . . . ? C5A C6A C7A C8A 0.7(4) . . . . ? C5A C6A C7A Cl1A 179.40(19) . . . . ? C6A C7A C8A C9A 0.2(4) . . . . ? Cl1A C7A C8A C9A -178.42(18) . . . . ? C1A N1A C9A C8A 179.9(2) . . . . ? C1A N1A C9A C4A -1.3(3) . . . . ? C7A C8A C9A N1A 177.6(2) . . . . ? C7A C8A C9A C4A -1.2(4) . . . . ? C5A C4A C9A N1A -177.6(2) . . . . ? C3A C4A C9A N1A 2.5(3) . . . . ? C5A C4A C9A C8A 1.2(3) . . . . ? C3A C4A C9A C8A -178.8(2) . . . . ? C3A N2A C10A C11A 173.4(2) . . . . ? N2A C10A C11A C12A -173.8(2) . . . . ? C10A C11A C12A C13A 178.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.31 _refine_diff_density_min -0.33 _refine_diff_density_rms 0.074 # Attachment '4_Cl.CIF' data_Cl _database_code_depnum_ccdc_archive 'CCDC 697894' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H10 Cl2 N2' _chemical_formula_sum 'C11 H10 Cl2 N2' _chemical_formula_weight 241.11 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc ' 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' _cell_length_a 4.6442(12) _cell_length_b 17.670(4) _cell_length_c 13.313(3) _cell_angle_alpha 90 _cell_angle_beta 100.024(2) _cell_angle_gamma 90 _cell_volume 1075.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 967 _cell_measurement_theta_min 4.5 _cell_measurement_theta_max 25.6 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.568 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.733 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.69050 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' # Station 9.8: R. J. Cernik, W. Clegg, C. R. A. Catlow, G. Bushnell-Wye, # J. V. Flaherty, G. N. Greaves, M. Hamichi, I. Burrows, D. J. Taylor # and S. J. Teat, # J. Synchotron Radiation 1997, 4, 279-286; 7, 40. # Synchrotron chemical crystallography: # W. Clegg, J. Chem. Soc., Dalton Trans. 2000, 3223-3232. # Contact: W. Clegg (0191 222 6649), w.clegg@ncl.ac.uk # R. W. Harrington (0191 222 6641), r.w.harrington@ncl.ac.uk _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 3681 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.058 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.5 _diffrn_reflns_theta_max 25.0 _reflns_number_total 1913 _reflns_number_gt 1889 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2, Bruker' # AXS Inc., Madison, USA, 2004 _computing_cell_refinement 'SAINT, Bruker' # AXS Inc., Madison, USA, 2004 _computing_data_reduction 'SAINT, Bruker' #AXS Inc., Madison, USA, 2004' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006' _computing_publication_material SHELXL97 _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^)+(0.0679P)^2^+0.0079P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.13(7) _refine_ls_number_reflns 1913 _refine_ls_number_parameters 139 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.038 _refine_ls_R_factor_gt 0.038 _refine_ls_wR_factor_ref 0.105 _refine_ls_wR_factor_gt 0.104 _refine_ls_goodness_of_fit_ref 1.11 _refine_ls_restrained_S_all 1.11 _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 -0.03321(12) 0.30872(4) 0.34632(5) 0.0233(2) Uani 1 1 d . . . Cl2 Cl 0.56584(13) 0.73633(4) 0.05279(5) 0.0222(2) Uani 1 1 d . . . N1 N 0.7012(6) 0.51598(14) 0.46306(18) 0.0208(5) Uani 1 1 d . . . N2 N 0.7814(5) 0.57656(13) 0.16188(16) 0.0176(5) Uani 1 1 d D . . H2N H 0.7206 0.5450 0.1115 0.021 Uiso 1 1 d D . . C1 C 0.8708(7) 0.57170(17) 0.4416(2) 0.0220(6) Uani 1 1 d . . . H1 H 0.9791 0.5983 0.4978 0.026 Uiso 1 1 calc R . . C2 C 0.9061(6) 0.59516(15) 0.3444(2) 0.0192(6) Uani 1 1 d . . . H2 H 1.0317 0.6364 0.3365 0.023 Uiso 1 1 calc R . . C3 C 0.7552(6) 0.55756(15) 0.2588(2) 0.0165(5) Uani 1 1 d . . . C4 C 0.5637(6) 0.49765(15) 0.2775(2) 0.0156(5) Uani 1 1 d . . . C5 C 0.3887(6) 0.45626(16) 0.1982(2) 0.0185(6) Uani 1 1 d . . . H5 H 0.3977 0.4680 0.1292 0.022 Uiso 1 1 calc R . . C6 C 0.2072(6) 0.39983(16) 0.2194(2) 0.0200(6) Uani 1 1 d . . . H6 H 0.0912 0.3727 0.1654 0.024 Uiso 1 1 calc R . . C7 C 0.1927(6) 0.38221(16) 0.3206(2) 0.0173(6) Uani 1 1 d . . . C8 C 0.3564(6) 0.42090(15) 0.4002(2) 0.0175(6) Uani 1 1 d . . . H8 H 0.3431 0.4082 0.4686 0.021 Uiso 1 1 calc R . . C9 C 0.5437(6) 0.47943(15) 0.3799(2) 0.0161(5) Uani 1 1 d . . . C10 C 0.9815(6) 0.63476(16) 0.1396(2) 0.0190(6) Uani 1 1 d . . . H10A H 1.0169 0.6275 0.0690 0.023 Uiso 1 1 calc R . . H10B H 1.1708 0.6283 0.1861 0.023 Uiso 1 1 calc R . . C11 C 0.8739(6) 0.71497(16) 0.1501(2) 0.0195(6) Uani 1 1 d . . . H11A H 1.0342 0.7510 0.1453 0.023 Uiso 1 1 calc R . . H11B H 0.8176 0.7212 0.2180 0.023 Uiso 1 1 calc R . . 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 0.0253(4) 0.0239(4) 0.0217(3) 0.0016(3) 0.0066(3) -0.0048(3) Cl2 0.0256(4) 0.0182(3) 0.0216(4) -0.0001(3) 0.0008(2) 0.0026(3) N1 0.0305(13) 0.0192(12) 0.0118(12) -0.0016(10) 0.0012(9) -0.0012(11) N2 0.0236(11) 0.0167(11) 0.0125(12) 0.0017(9) 0.0033(9) 0.0017(9) C1 0.0302(14) 0.0204(14) 0.0134(13) -0.0036(11) -0.0015(11) -0.0023(12) C2 0.0221(15) 0.0180(13) 0.0169(13) 0.0024(11) 0.0019(11) 0.0005(11) C3 0.0206(12) 0.0158(12) 0.0132(13) -0.0006(10) 0.0035(10) 0.0027(10) C4 0.0207(13) 0.0150(12) 0.0114(13) 0.0014(10) 0.0039(10) 0.0059(10) C5 0.0265(14) 0.0189(14) 0.0106(12) 0.0002(10) 0.0042(10) 0.0024(10) C6 0.0223(14) 0.0214(14) 0.0147(13) -0.0018(11) -0.0010(10) 0.0008(11) C7 0.0177(13) 0.0161(13) 0.0181(14) -0.0008(10) 0.0034(10) 0.0004(10) C8 0.0226(13) 0.0198(14) 0.0112(12) 0.0015(11) 0.0060(10) 0.0045(11) C9 0.0207(13) 0.0158(12) 0.0114(13) -0.0001(10) 0.0021(10) 0.0049(10) C10 0.0211(13) 0.0207(13) 0.0171(12) 0.0038(11) 0.0085(11) 0.0033(11) C11 0.0202(13) 0.0212(14) 0.0165(14) 0.0015(11) 0.0016(10) -0.0005(11) _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 C7 1.741(3) . ? Cl2 C11 1.795(3) . ? N1 C1 1.323(4) . ? N1 C9 1.377(4) . ? N2 C3 1.359(4) . ? N2 C10 1.451(3) . ? N2 H2N 0.8800 . ? C1 C2 1.395(4) . ? C1 H1 0.9500 . ? C2 C3 1.397(4) . ? C2 H2 0.9500 . ? C3 C4 1.432(4) . ? C4 C5 1.418(4) . ? C4 C9 1.420(4) . ? C5 C6 1.366(4) . ? C5 H5 0.9500 . ? C6 C7 1.395(4) . ? C6 H6 0.9500 . ? C7 C8 1.374(4) . ? C8 C9 1.408(4) . ? C8 H8 0.9500 . ? C10 C11 1.517(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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 C9 115.3(2) . . ? C3 N2 C10 122.4(2) . . ? C3 N2 H2N 119.8 . . ? C10 N2 H2N 115.1 . . ? N1 C1 C2 126.3(3) . . ? N1 C1 H1 116.8 . . ? C2 C1 H1 116.8 . . ? C1 C2 C3 119.4(3) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? N2 C3 C2 122.8(2) . . ? N2 C3 C4 120.6(2) . . ? C2 C3 C4 116.7(2) . . ? C5 C4 C9 118.2(3) . . ? C5 C4 C3 123.0(3) . . ? C9 C4 C3 118.7(2) . . ? C6 C5 C4 121.1(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 119.8(3) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 121.4(3) . . ? C8 C7 Cl1 119.4(2) . . ? C6 C7 Cl1 119.3(2) . . ? C7 C8 C9 119.7(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? N1 C9 C8 116.7(2) . . ? N1 C9 C4 123.5(3) . . ? C8 C9 C4 119.8(2) . . ? N2 C10 C11 114.2(2) . . ? N2 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? N2 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 Cl2 111.3(2) . . ? C10 C11 H11A 109.4 . . ? Cl2 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? Cl2 C11 H11B 109.4 . . ? H11A C11 H11B 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 C9 N1 C1 C2 -1.0(4) . . . . ? N1 C1 C2 C3 -0.8(5) . . . . ? C10 N2 C3 C2 3.6(4) . . . . ? C10 N2 C3 C4 -177.4(2) . . . . ? C1 C2 C3 N2 -179.1(3) . . . . ? C1 C2 C3 C4 1.9(4) . . . . ? N2 C3 C4 C5 -1.3(4) . . . . ? C2 C3 C4 C5 177.7(2) . . . . ? N2 C3 C4 C9 179.8(2) . . . . ? C2 C3 C4 C9 -1.2(4) . . . . ? C9 C4 C5 C6 -0.6(4) . . . . ? C3 C4 C5 C6 -179.5(2) . . . . ? C4 C5 C6 C7 0.0(4) . . . . ? C5 C6 C7 C8 0.5(4) . . . . ? C5 C6 C7 Cl1 -178.5(2) . . . . ? C6 C7 C8 C9 -0.2(4) . . . . ? Cl1 C7 C8 C9 178.79(19) . . . . ? C1 N1 C9 C8 -178.7(2) . . . . ? C1 N1 C9 C4 1.7(4) . . . . ? C7 C8 C9 N1 179.9(2) . . . . ? C7 C8 C9 C4 -0.4(4) . . . . ? C5 C4 C9 N1 -179.5(3) . . . . ? C3 C4 C9 N1 -0.6(4) . . . . ? C5 C4 C9 C8 0.8(4) . . . . ? C3 C4 C9 C8 179.8(2) . . . . ? C3 N2 C10 C11 -77.8(3) . . . . ? N2 C10 C11 Cl2 -68.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.41 _refine_diff_density_min -0.35 _refine_diff_density_rms 0.097 # Attachment '5_azide.CIF' data_azide _database_code_depnum_ccdc_archive 'CCDC 697895' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H10 Cl N5' _chemical_formula_sum 'C11 H10 Cl N5' _chemical_formula_weight 247.69 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 13.0426(5) _cell_length_b 7.8693(2) _cell_length_c 22.6276(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2322.41(14) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2928 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.313 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.866 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16466 _diffrn_reflns_av_R_equivalents 0.060 _diffrn_reflns_av_sigmaI/netI 0.037 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 27.4 _reflns_number_total 2630 _reflns_number_gt 2120 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006' _computing_publication_material SHELXL97 _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^)+(0.0184P)^2^+3.7962P] 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 2630 _refine_ls_number_parameters 157 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.067 _refine_ls_R_factor_gt 0.051 _refine_ls_wR_factor_ref 0.105 _refine_ls_wR_factor_gt 0.096 _refine_ls_goodness_of_fit_ref 1.08 _refine_ls_restrained_S_all 1.08 _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 0.18786(5) 0.15546(8) 0.55167(2) 0.02836(16) Uani 1 1 d . . . N1 N 0.04322(14) 0.4454(2) 0.73332(8) 0.0221(4) Uani 1 1 d . . . N2 N 0.33271(14) 0.4890(2) 0.81559(8) 0.0195(4) Uani 1 1 d D . . H2N H 0.3893 0.4582 0.7973 0.023 Uiso 1 1 d D . . N3 N 0.38215(17) 0.3364(3) 0.93286(8) 0.0300(5) Uani 1 1 d . . . N4 N 0.42405(16) 0.3219(3) 0.98157(9) 0.0280(5) Uani 1 1 d . . . N5 N 0.46696(18) 0.2953(3) 1.02406(10) 0.0420(6) Uani 1 1 d . . . C1 C 0.05692(17) 0.5176(3) 0.78566(10) 0.0222(5) Uani 1 1 d . . . H1 H -0.0024 0.5601 0.8050 0.027 Uiso 1 1 calc R . . C2 C 0.15004(17) 0.5371(3) 0.81489(10) 0.0202(5) Uani 1 1 d . . . H2 H 0.1524 0.5929 0.8521 0.024 Uiso 1 1 calc R . . C3 C 0.24005(16) 0.4747(3) 0.78950(9) 0.0161(4) Uani 1 1 d . . . C4 C 0.22938(16) 0.3926(3) 0.73261(9) 0.0159(4) Uani 1 1 d . . . C5 C 0.31378(16) 0.3258(3) 0.70103(9) 0.0184(4) Uani 1 1 d . . . H5 H 0.3802 0.3299 0.7182 0.022 Uiso 1 1 calc R . . C6 C 0.30170(17) 0.2550(3) 0.64600(10) 0.0211(5) Uani 1 1 d . . . H6 H 0.3590 0.2116 0.6250 0.025 Uiso 1 1 calc R . . C7 C 0.20268(18) 0.2482(3) 0.62136(9) 0.0203(5) Uani 1 1 d . . . C8 C 0.11901(17) 0.3108(3) 0.64994(9) 0.0197(4) Uani 1 1 d . . . H8 H 0.0533 0.3053 0.6319 0.024 Uiso 1 1 calc R . . C9 C 0.13036(16) 0.3843(3) 0.70677(9) 0.0180(4) Uani 1 1 d . . . C10 C 0.34908(18) 0.5853(3) 0.86968(10) 0.0225(5) Uani 1 1 d . . . H10A H 0.3093 0.6923 0.8673 0.027 Uiso 1 1 calc R . . H10B H 0.4225 0.6160 0.8723 0.027 Uiso 1 1 calc R . . C11 C 0.31863(18) 0.4918(3) 0.92580(10) 0.0237(5) Uani 1 1 d . . . H11A H 0.3284 0.5672 0.9604 0.028 Uiso 1 1 calc R . . H11B H 0.2453 0.4601 0.9238 0.028 Uiso 1 1 calc R . . 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 0.0327(3) 0.0361(3) 0.0163(3) -0.0049(2) -0.0020(2) 0.0009(3) N1 0.0148(9) 0.0267(10) 0.0248(10) -0.0015(8) 0.0004(8) 0.0003(8) N2 0.0162(9) 0.0267(10) 0.0156(9) -0.0014(8) 0.0006(7) -0.0003(8) N3 0.0418(12) 0.0312(11) 0.0169(9) -0.0020(8) -0.0054(9) 0.0041(10) N4 0.0246(10) 0.0380(12) 0.0215(10) 0.0010(9) 0.0036(9) -0.0011(9) N5 0.0317(12) 0.0705(17) 0.0237(11) 0.0045(11) -0.0029(10) 0.0066(12) C1 0.0177(11) 0.0243(12) 0.0246(11) -0.0014(9) 0.0043(9) 0.0031(9) C2 0.0194(11) 0.0221(11) 0.0191(11) -0.0016(9) 0.0022(9) 0.0006(9) C3 0.0177(10) 0.0174(10) 0.0134(9) 0.0027(8) -0.0002(8) 0.0008(8) C4 0.0154(10) 0.0150(10) 0.0174(10) 0.0025(8) 0.0010(8) -0.0007(8) C5 0.0158(10) 0.0213(10) 0.0181(10) 0.0034(8) 0.0002(8) 0.0015(9) C6 0.0211(11) 0.0244(11) 0.0178(10) 0.0038(9) 0.0041(9) 0.0036(9) C7 0.0276(12) 0.0212(10) 0.0121(10) 0.0006(8) 0.0001(9) -0.0016(9) C8 0.0168(10) 0.0215(11) 0.0208(11) 0.0024(9) -0.0031(9) -0.0016(9) C9 0.0151(10) 0.0192(10) 0.0197(10) 0.0017(8) 0.0007(8) -0.0001(8) C10 0.0231(11) 0.0245(12) 0.0198(11) -0.0042(9) -0.0038(9) -0.0021(9) C11 0.0257(12) 0.0278(12) 0.0175(10) -0.0031(9) 0.0009(9) 0.0005(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C7 1.748(2) . ? N1 C1 1.326(3) . ? N1 C9 1.372(3) . ? N2 C3 1.350(3) . ? N2 C10 1.456(3) . ? N2 H2N 0.8800 . ? N3 N4 1.235(3) . ? N3 C11 1.486(3) . ? N4 N5 1.132(3) . ? C1 C2 1.391(3) . ? C1 H1 0.9500 . ? C2 C3 1.396(3) . ? C2 H2 0.9500 . ? C3 C4 1.447(3) . ? C4 C5 1.414(3) . ? C4 C9 1.419(3) . ? C5 C6 1.373(3) . ? C5 H5 0.9500 . ? C6 C7 1.408(3) . ? C6 H6 0.9500 . ? C7 C8 1.361(3) . ? C8 C9 1.418(3) . ? C8 H8 0.9500 . ? C10 C11 1.520(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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 C9 115.44(19) . . ? C3 N2 C10 122.86(18) . . ? C3 N2 H2N 121.5 . . ? C10 N2 H2N 114.5 . . ? N4 N3 C11 114.76(19) . . ? N5 N4 N3 173.4(3) . . ? N1 C1 C2 126.1(2) . . ? N1 C1 H1 116.9 . . ? C2 C1 H1 116.9 . . ? C1 C2 C3 120.0(2) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? N2 C3 C2 122.92(19) . . ? N2 C3 C4 120.83(19) . . ? C2 C3 C4 116.25(19) . . ? C5 C4 C9 118.90(19) . . ? C5 C4 C3 122.74(19) . . ? C9 C4 C3 118.33(19) . . ? C6 C5 C4 121.3(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 118.7(2) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C8 C7 C6 122.2(2) . . ? C8 C7 Cl1 119.42(17) . . ? C6 C7 Cl1 118.34(17) . . ? C7 C8 C9 119.7(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? N1 C9 C8 116.97(19) . . ? N1 C9 C4 123.86(19) . . ? C8 C9 C4 119.17(19) . . ? N2 C10 C11 114.31(19) . . ? N2 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? N2 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? N3 C11 C10 110.04(19) . . ? N3 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? N3 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? 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 C11 N3 N4 N5 -175(2) . . . . ? C9 N1 C1 C2 0.5(3) . . . . ? N1 C1 C2 C3 -1.3(4) . . . . ? C10 N2 C3 C2 -6.3(3) . . . . ? C10 N2 C3 C4 173.50(19) . . . . ? C1 C2 C3 N2 -179.8(2) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? N2 C3 C4 C5 -0.9(3) . . . . ? C2 C3 C4 C5 178.9(2) . . . . ? N2 C3 C4 C9 -178.74(19) . . . . ? C2 C3 C4 C9 1.1(3) . . . . ? C9 C4 C5 C6 0.6(3) . . . . ? C3 C4 C5 C6 -177.2(2) . . . . ? C4 C5 C6 C7 -0.7(3) . . . . ? C5 C6 C7 C8 0.7(3) . . . . ? C5 C6 C7 Cl1 -179.21(17) . . . . ? C6 C7 C8 C9 -0.7(3) . . . . ? Cl1 C7 C8 C9 179.26(16) . . . . ? C1 N1 C9 C8 -178.2(2) . . . . ? C1 N1 C9 C4 1.2(3) . . . . ? C7 C8 C9 N1 179.9(2) . . . . ? C7 C8 C9 C4 0.6(3) . . . . ? C5 C4 C9 N1 -179.9(2) . . . . ? C3 C4 C9 N1 -1.9(3) . . . . ? C5 C4 C9 C8 -0.5(3) . . . . ? C3 C4 C9 C8 177.38(19) . . . . ? C3 N2 C10 C11 80.0(3) . . . . ? N4 N3 C11 C10 128.5(2) . . . . ? N2 C10 C11 N3 62.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.4 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.29 _refine_diff_density_min -0.28 _refine_diff_density_rms 0.062 # Attachment '6_CH2CH2OH.CIF' data_CH2CH2OH _database_code_depnum_ccdc_archive 'CCDC 697896' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 Cl N2 O' _chemical_formula_sum 'C11 H11 Cl N2 O' _chemical_formula_weight 222.67 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' O O 0.0106 0.0060 '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/n' _symmetry_space_group_name_Hall '-P 2yn ' 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 4.5721(1) _cell_length_b 14.8383(6) _cell_length_c 14.8932(6) _cell_angle_alpha 90 _cell_angle_beta 93.546(3) _cell_angle_gamma 90 _cell_volume 1008.45(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2324 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.350 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.721 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13921 _diffrn_reflns_av_R_equivalents 0.068 _diffrn_reflns_av_sigmaI/netI 0.048 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 27.5 _reflns_number_total 2296 _reflns_number_gt 1624 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006' _computing_publication_material SHELXL97 _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^)+(0.0447P)^2^+0.4254P] 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 2296 _refine_ls_number_parameters 142 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.071 _refine_ls_R_factor_gt 0.041 _refine_ls_wR_factor_ref 0.104 _refine_ls_wR_factor_gt 0.091 _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_restrained_S_all 1.05 _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 1.08404(11) 0.09498(4) 0.42344(3) 0.02970(17) Uani 1 1 d . . . O1 O -0.0263(3) 0.05329(9) -0.09674(9) 0.0227(3) Uani 1 1 d D . . H1O H -0.0115 0.0863 -0.1421 0.034 Uiso 1 1 d D . . N1 N 0.4712(4) 0.33259(11) 0.25709(11) 0.0240(4) Uani 1 1 d . . . N2 N 0.0711(3) 0.14634(11) 0.07666(11) 0.0212(4) Uani 1 1 d D . . H2N H 0.0755 0.0887 0.0904 0.025 Uiso 1 1 d D . . C1 C 0.2803(4) 0.35592(13) 0.19085(13) 0.0259(5) Uani 1 1 d . . . H1 H 0.2329 0.4181 0.1854 0.031 Uiso 1 1 calc R . . C2 C 0.1430(4) 0.29777(13) 0.12867(13) 0.0228(4) Uani 1 1 d . . . H2 H 0.0105 0.3205 0.0825 0.027 Uiso 1 1 calc R . . C3 C 0.2009(4) 0.20630(12) 0.13447(12) 0.0177(4) Uani 1 1 d . . . C4 C 0.4151(4) 0.17727(12) 0.20328(12) 0.0182(4) Uani 1 1 d . . . C5 C 0.5080(4) 0.08725(13) 0.21360(13) 0.0213(4) Uani 1 1 d . . . H5 H 0.4266 0.0428 0.1735 0.026 Uiso 1 1 calc R . . C6 C 0.7115(4) 0.06206(13) 0.27956(13) 0.0222(4) Uani 1 1 d . . . H6 H 0.7711 0.0009 0.2856 0.027 Uiso 1 1 calc R . . C7 C 0.8310(4) 0.12808(13) 0.33829(12) 0.0206(4) Uani 1 1 d . . . C8 C 0.7517(4) 0.21577(13) 0.33010(12) 0.0206(4) Uani 1 1 d . . . H8 H 0.8384 0.2592 0.3704 0.025 Uiso 1 1 calc R . . C9 C 0.5416(4) 0.24313(13) 0.26232(12) 0.0194(4) Uani 1 1 d . . . C10 C -0.1488(4) 0.17288(13) 0.00730(12) 0.0202(4) Uani 1 1 d . . . H10A H -0.0654 0.2183 -0.0325 0.024 Uiso 1 1 calc R . . H10B H -0.3178 0.2005 0.0354 0.024 Uiso 1 1 calc R . . C11 C -0.2501(4) 0.09223(13) -0.04726(13) 0.0224(4) Uani 1 1 d . . . H11A H -0.3246 0.0461 -0.0064 0.027 Uiso 1 1 calc R . . H11B H -0.4148 0.1105 -0.0897 0.027 Uiso 1 1 calc R . . 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 0.0309(3) 0.0308(3) 0.0264(3) -0.0007(2) -0.0069(2) -0.0001(2) O1 0.0308(8) 0.0171(7) 0.0198(7) 0.0013(6) -0.0026(6) 0.0019(6) N1 0.0298(9) 0.0174(9) 0.0250(9) -0.0044(7) 0.0028(7) -0.0005(7) N2 0.0245(9) 0.0175(8) 0.0212(9) 0.0010(7) -0.0016(7) -0.0007(7) C1 0.0304(11) 0.0179(10) 0.0298(12) 0.0001(8) 0.0054(9) 0.0016(8) C2 0.0253(10) 0.0214(10) 0.0218(10) 0.0002(8) 0.0013(8) 0.0026(8) C3 0.0184(9) 0.0171(9) 0.0180(9) -0.0008(7) 0.0054(7) -0.0020(7) C4 0.0196(10) 0.0171(9) 0.0180(9) -0.0014(7) 0.0038(7) -0.0024(8) C5 0.0250(10) 0.0178(10) 0.0210(10) -0.0030(8) 0.0012(8) -0.0038(8) C6 0.0254(11) 0.0193(10) 0.0218(10) -0.0007(8) 0.0014(8) -0.0015(8) C7 0.0189(10) 0.0253(10) 0.0176(10) -0.0016(8) 0.0009(8) -0.0022(8) C8 0.0226(10) 0.0210(10) 0.0186(10) -0.0051(8) 0.0035(8) -0.0046(8) C9 0.0214(10) 0.0181(10) 0.0194(10) -0.0030(7) 0.0071(8) -0.0030(8) C10 0.0205(10) 0.0203(10) 0.0200(10) 0.0018(8) 0.0028(8) 0.0016(8) C11 0.0200(10) 0.0208(10) 0.0257(11) 0.0024(8) -0.0024(8) -0.0018(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 Cl1 C7 1.7339(19) . ? O1 C11 1.420(2) . ? O1 H1O 0.8400 . ? N1 C1 1.322(3) . ? N1 C9 1.367(2) . ? N2 C3 1.350(2) . ? N2 C10 1.451(2) . ? N2 H2N 0.8799 . ? C1 C2 1.387(3) . ? C1 H1 0.9500 . ? C2 C3 1.384(3) . ? C2 H2 0.9500 . ? C3 C4 1.439(3) . ? C4 C5 1.407(3) . ? C4 C9 1.414(3) . ? C5 C6 1.363(3) . ? C5 H5 0.9500 . ? C6 C7 1.401(3) . ? C6 H6 0.9500 . ? C7 C8 1.354(3) . ? C8 C9 1.410(3) . ? C8 H8 0.9500 . ? C10 C11 1.503(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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 C11 O1 H1O 106.1 . . ? C1 N1 C9 116.03(16) . . ? C3 N2 C10 122.22(16) . . ? C3 N2 H2N 119.3 . . ? C10 N2 H2N 115.7 . . ? N1 C1 C2 125.86(18) . . ? N1 C1 H1 117.1 . . ? C2 C1 H1 117.1 . . ? C3 C2 C1 119.44(18) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? N2 C3 C2 122.13(17) . . ? N2 C3 C4 120.65(16) . . ? C2 C3 C4 117.18(17) . . ? C5 C4 C9 118.63(17) . . ? C5 C4 C3 123.33(17) . . ? C9 C4 C3 118.03(17) . . ? C6 C5 C4 121.81(18) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C7 118.73(18) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C8 C7 C6 121.57(18) . . ? C8 C7 Cl1 120.05(15) . . ? C6 C7 Cl1 118.38(15) . . ? C7 C8 C9 120.53(17) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? N1 C9 C8 117.91(17) . . ? N1 C9 C4 123.37(17) . . ? C8 C9 C4 118.73(17) . . ? N2 C10 C11 110.22(15) . . ? N2 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? N2 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? O1 C11 C10 113.35(15) . . ? O1 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? O1 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? 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 C9 N1 C1 C2 1.6(3) . . . . ? N1 C1 C2 C3 1.0(3) . . . . ? C10 N2 C3 C2 -3.2(3) . . . . ? C10 N2 C3 C4 179.07(16) . . . . ? C1 C2 C3 N2 179.12(18) . . . . ? C1 C2 C3 C4 -3.1(3) . . . . ? N2 C3 C4 C5 1.7(3) . . . . ? C2 C3 C4 C5 -176.19(18) . . . . ? N2 C3 C4 C9 -179.47(17) . . . . ? C2 C3 C4 C9 2.7(3) . . . . ? C9 C4 C5 C6 1.1(3) . . . . ? C3 C4 C5 C6 180.00(17) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 -0.9(3) . . . . ? C5 C6 C7 Cl1 178.68(15) . . . . ? C6 C7 C8 C9 0.9(3) . . . . ? Cl1 C7 C8 C9 -178.64(14) . . . . ? C1 N1 C9 C8 177.91(17) . . . . ? C1 N1 C9 C4 -1.9(3) . . . . ? C7 C8 C9 N1 -179.73(18) . . . . ? C7 C8 C9 C4 0.1(3) . . . . ? C5 C4 C9 N1 178.74(18) . . . . ? C3 C4 C9 N1 -0.2(3) . . . . ? C5 C4 C9 C8 -1.1(3) . . . . ? C3 C4 C9 C8 179.99(16) . . . . ? C3 N2 C10 C11 179.24(16) . . . . ? N2 C10 C11 O1 -64.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.28 _refine_diff_density_min -0.30 _refine_diff_density_rms 0.065 # Attachment '7_racemic.CIF' data_racemic _database_code_depnum_ccdc_archive 'CCDC 697897' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 Cl N2 O' _chemical_formula_sum 'C13 H15 Cl N2 O' _chemical_formula_weight 250.72 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' O O 0.0106 0.0060 '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/c' _symmetry_space_group_name_Hall '-P 2ybc ' 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 8.9290(3) _cell_length_b 15.0394(5) _cell_length_c 9.2127(2) _cell_angle_alpha 90 _cell_angle_beta 105.198(2) _cell_angle_gamma 90 _cell_volume 1193.88(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2797 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.788 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14685 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.028 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 27.5 _reflns_number_total 2722 _reflns_number_gt 2403 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006' _computing_publication_material SHELXL97 _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^)+(0.0321P)^2^+0.9182P] 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 2722 _refine_ls_number_parameters 160 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.044 _refine_ls_R_factor_gt 0.036 _refine_ls_wR_factor_ref 0.090 _refine_ls_wR_factor_gt 0.086 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _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 -0.12317(4) 0.57665(3) 0.08343(4) 0.02147(12) Uani 1 1 d . . . O1 O 0.53589(12) 0.14003(7) 0.88664(12) 0.0190(2) Uani 1 1 d D . . H1O H 0.6315 0.1511 0.9121 0.029 Uiso 1 1 d D . . N1 N -0.14597(14) 0.33202(9) 0.45916(14) 0.0174(3) Uani 1 1 d . . . N2 N 0.34189(14) 0.31236(9) 0.60869(14) 0.0187(3) Uani 1 1 d D . . H2N H 0.3953 0.3375 0.5520 0.022 Uiso 1 1 d D . . C1 C -0.07401(18) 0.27812(10) 0.56941(17) 0.0182(3) Uani 1 1 d . . . H1 H -0.1374 0.2427 0.6148 0.022 Uiso 1 1 calc R . . C2 C 0.08618(17) 0.26873(10) 0.62469(16) 0.0167(3) Uani 1 1 d . . . H2 H 0.1277 0.2280 0.7038 0.020 Uiso 1 1 calc R . . C3 C 0.18478(16) 0.31932(10) 0.56345(16) 0.0140(3) Uani 1 1 d . . . C4 C 0.11285(16) 0.38219(9) 0.44795(15) 0.0131(3) Uani 1 1 d . . . C5 C 0.19864(17) 0.44408(10) 0.38554(17) 0.0164(3) Uani 1 1 d . . . H5 H 0.3087 0.4446 0.4199 0.020 Uiso 1 1 calc R . . C6 C 0.12585(18) 0.50299(10) 0.27686(17) 0.0176(3) Uani 1 1 d . . . H6 H 0.1848 0.5443 0.2366 0.021 Uiso 1 1 calc R . . C7 C -0.03687(17) 0.50198(10) 0.22506(16) 0.0156(3) Uani 1 1 d . . . C8 C -0.12511(17) 0.44530(10) 0.28400(16) 0.0161(3) Uani 1 1 d . . . H8 H -0.2350 0.4464 0.2483 0.019 Uiso 1 1 calc R . . C9 C -0.05184(16) 0.38477(9) 0.39882(16) 0.0138(3) Uani 1 1 d . . . C10 C 0.42806(17) 0.27641(10) 0.75468(17) 0.0180(3) Uani 1 1 d . . . H10 H 0.3598 0.2805 0.8248 0.022 Uiso 1 1 calc R . . C11 C 0.46973(17) 0.17824(10) 0.74232(17) 0.0183(3) Uani 1 1 d . . . H11A H 0.3751 0.1448 0.6914 0.022 Uiso 1 1 calc R . . H11B H 0.5445 0.1732 0.6802 0.022 Uiso 1 1 calc R . . C12 C 0.57109(18) 0.33371(11) 0.81834(18) 0.0209(3) Uani 1 1 d . . . H12A H 0.6318 0.3073 0.9142 0.025 Uiso 1 1 calc R . . H12B H 0.6371 0.3331 0.7472 0.025 Uiso 1 1 calc R . . C13 C 0.5320(2) 0.42974(11) 0.8465(2) 0.0267(4) Uani 1 1 d . . . H13A H 0.6282 0.4632 0.8867 0.040 Uiso 1 1 calc R . . H13B H 0.4692 0.4311 0.9191 0.040 Uiso 1 1 calc R . . H13C H 0.4736 0.4567 0.7517 0.040 Uiso 1 1 calc R . . 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 0.0244(2) 0.0218(2) 0.01700(19) 0.00545(14) 0.00335(14) 0.00454(15) O1 0.0114(5) 0.0216(6) 0.0222(6) 0.0045(4) 0.0010(4) 0.0005(4) N1 0.0130(6) 0.0177(6) 0.0206(6) 0.0018(5) 0.0030(5) -0.0015(5) N2 0.0112(6) 0.0253(7) 0.0179(6) 0.0058(5) 0.0007(5) -0.0002(5) C1 0.0163(7) 0.0172(7) 0.0213(7) 0.0019(6) 0.0051(6) -0.0027(6) C2 0.0176(7) 0.0160(7) 0.0156(7) 0.0019(5) 0.0025(5) 0.0002(6) C3 0.0127(7) 0.0144(7) 0.0135(6) -0.0033(5) 0.0011(5) -0.0003(5) C4 0.0136(7) 0.0134(7) 0.0117(6) -0.0030(5) 0.0025(5) 0.0001(5) C5 0.0136(7) 0.0188(7) 0.0170(7) -0.0012(6) 0.0045(5) -0.0008(6) C6 0.0181(7) 0.0180(7) 0.0180(7) 0.0007(6) 0.0068(6) -0.0012(6) C7 0.0200(7) 0.0143(7) 0.0119(6) 0.0001(5) 0.0031(5) 0.0040(6) C8 0.0133(7) 0.0173(7) 0.0162(7) -0.0017(6) 0.0012(5) 0.0007(6) C9 0.0133(7) 0.0138(7) 0.0139(7) -0.0030(5) 0.0028(5) -0.0009(5) C10 0.0142(7) 0.0197(8) 0.0172(7) 0.0014(6) -0.0012(5) -0.0001(6) C11 0.0158(7) 0.0196(8) 0.0176(7) -0.0002(6) 0.0011(6) 0.0017(6) C12 0.0160(7) 0.0212(8) 0.0240(8) -0.0017(6) 0.0027(6) 0.0005(6) C13 0.0228(8) 0.0211(8) 0.0362(10) -0.0067(7) 0.0077(7) -0.0016(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 Cl1 C7 1.7408(15) . ? O1 C11 1.4266(18) . ? O1 H1O 0.8400 . ? N1 C1 1.3265(19) . ? N1 C9 1.3747(19) . ? N2 C3 1.3587(19) . ? N2 C10 1.4666(18) . ? N2 H2N 0.8799 . ? C1 C2 1.394(2) . ? C1 H1 0.9500 . ? C2 C3 1.390(2) . ? C2 H2 0.9500 . ? C3 C4 1.442(2) . ? C4 C5 1.419(2) . ? C4 C9 1.4212(19) . ? C5 C6 1.367(2) . ? C5 H5 0.9500 . ? C6 C7 1.405(2) . ? C6 H6 0.9500 . ? C7 C8 1.366(2) . ? C8 C9 1.419(2) . ? C8 H8 0.9500 . ? C10 C12 1.525(2) . ? C10 C11 1.534(2) . ? C10 H10 1.0000 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.524(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 C11 O1 H1O 108.8 . . ? C1 N1 C9 115.95(13) . . ? C3 N2 C10 124.13(13) . . ? C3 N2 H2N 117.5 . . ? C10 N2 H2N 117.9 . . ? N1 C1 C2 125.90(14) . . ? N1 C1 H1 117.1 . . ? C2 C1 H1 117.1 . . ? C3 C2 C1 119.64(14) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? N2 C3 C2 123.10(13) . . ? N2 C3 C4 120.08(13) . . ? C2 C3 C4 116.82(13) . . ? C5 C4 C9 118.45(13) . . ? C5 C4 C3 123.05(13) . . ? C9 C4 C3 118.45(13) . . ? C6 C5 C4 121.21(14) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 119.50(14) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 121.62(14) . . ? C8 C7 Cl1 120.82(12) . . ? C6 C7 Cl1 117.55(11) . . ? C7 C8 C9 119.70(13) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? N1 C9 C8 117.42(13) . . ? N1 C9 C4 123.14(13) . . ? C8 C9 C4 119.43(13) . . ? N2 C10 C12 109.24(13) . . ? N2 C10 C11 111.46(12) . . ? C12 C10 C11 112.18(12) . . ? N2 C10 H10 107.9 . . ? C12 C10 H10 107.9 . . ? C11 C10 H10 107.9 . . ? O1 C11 C10 111.57(12) . . ? O1 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? O1 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C10 113.27(13) . . ? C13 C12 H12A 108.9 . . ? C10 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C10 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C9 N1 C1 C2 -2.2(2) . . . . ? N1 C1 C2 C3 0.5(2) . . . . ? C10 N2 C3 C2 -21.7(2) . . . . ? C10 N2 C3 C4 157.59(14) . . . . ? C1 C2 C3 N2 -178.33(14) . . . . ? C1 C2 C3 C4 2.4(2) . . . . ? N2 C3 C4 C5 -5.5(2) . . . . ? C2 C3 C4 C5 173.80(14) . . . . ? N2 C3 C4 C9 177.22(13) . . . . ? C2 C3 C4 C9 -3.50(19) . . . . ? C9 C4 C5 C6 -2.3(2) . . . . ? C3 C4 C5 C6 -179.56(14) . . . . ? C4 C5 C6 C7 -0.4(2) . . . . ? C5 C6 C7 C8 2.1(2) . . . . ? C5 C6 C7 Cl1 -178.51(11) . . . . ? C6 C7 C8 C9 -0.9(2) . . . . ? Cl1 C7 C8 C9 179.67(11) . . . . ? C1 N1 C9 C8 -178.00(13) . . . . ? C1 N1 C9 C4 0.8(2) . . . . ? C7 C8 C9 N1 177.08(13) . . . . ? C7 C8 C9 C4 -1.8(2) . . . . ? C5 C4 C9 N1 -175.47(13) . . . . ? C3 C4 C9 N1 2.0(2) . . . . ? C5 C4 C9 C8 3.4(2) . . . . ? C3 C4 C9 C8 -179.22(13) . . . . ? C3 N2 C10 C12 -138.23(15) . . . . ? C3 N2 C10 C11 97.24(17) . . . . ? N2 C10 C11 O1 -172.58(12) . . . . ? C12 C10 C11 O1 64.56(16) . . . . ? N2 C10 C12 C13 61.63(18) . . . . ? C11 C10 C12 C13 -174.26(13) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.52 _refine_diff_density_min -0.24 _refine_diff_density_rms 0.052 # Attachment '8_chiral.CIF' data_chiral _database_code_depnum_ccdc_archive 'CCDC 697898' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 Cl N2 O' _chemical_formula_sum 'C13 H15 Cl N2 O' _chemical_formula_weight 250.72 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' O O 0.0106 0.0060 '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' _symmetry_space_group_name_Hall 'P 2yb ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.7612(3) _cell_length_b 7.0756(1) _cell_length_c 9.6622(2) _cell_angle_alpha 90 _cell_angle_beta 95.644(1) _cell_angle_gamma 90 _cell_volume 596.06(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1445 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8587 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.033 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.0 _diffrn_reflns_theta_max 27.5 _reflns_number_total 2706 _reflns_number_gt 2601 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006' _computing_publication_material SHELXL97 _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. ; _chemical_absolute_configuration rm _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^)+(0.0363P)^2^+0.1464P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(5) _refine_ls_number_reflns 2706 _refine_ls_number_parameters 160 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.032 _refine_ls_R_factor_gt 0.030 _refine_ls_wR_factor_ref 0.073 _refine_ls_wR_factor_gt 0.071 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _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 1.11691(4) 0.29708(6) 0.60467(3) 0.02007(10) Uani 1 1 d . . . O1 O 0.53033(12) 0.61227(16) -0.15388(12) 0.0174(2) Uani 1 1 d D . . H1O H 0.6242 0.6243 -0.1281 0.026 Uiso 1 1 d D . . N1 N 1.16399(14) 0.18760(18) 0.09238(13) 0.0131(3) Uani 1 1 d . . . N2 N 0.69112(13) 0.2749(2) -0.02025(12) 0.0128(3) Uani 1 1 d D . . H2N H 0.6263 0.2487 0.0411 0.015 Uiso 1 1 d D . . C1 C 1.10172(17) 0.1833(2) -0.03890(16) 0.0144(3) Uani 1 1 d . . . H1 H 1.1689 0.1626 -0.1088 0.017 Uiso 1 1 calc R . . C2 C 0.94665(17) 0.2065(2) -0.08257(15) 0.0139(3) Uani 1 1 d . . . H2 H 0.9120 0.2007 -0.1788 0.017 Uiso 1 1 calc R . . C3 C 0.84203(17) 0.23842(19) 0.01482(15) 0.0119(3) Uani 1 1 d . . . C4 C 0.90394(17) 0.24215(19) 0.15942(15) 0.0119(3) Uani 1 1 d . . . C5 C 0.81293(16) 0.2804(2) 0.26961(14) 0.0138(3) Uani 1 1 d . . . H5 H 0.7052 0.2951 0.2497 0.017 Uiso 1 1 calc R . . C6 C 0.87729(16) 0.2965(3) 0.40450(14) 0.0155(3) Uani 1 1 d . . . H6 H 0.8151 0.3231 0.4773 0.019 Uiso 1 1 calc R . . C7 C 1.03652(17) 0.2731(2) 0.43324(14) 0.0150(3) Uani 1 1 d . . . C8 C 1.12892(18) 0.2321(2) 0.33139(16) 0.0142(3) Uani 1 1 d . . . H8 H 1.2357 0.2128 0.3542 0.017 Uiso 1 1 calc R . . C9 C 1.06414(17) 0.2184(2) 0.19075(15) 0.0125(3) Uani 1 1 d . . . C10 C 0.62126(15) 0.2814(2) -0.16458(14) 0.0123(3) Uani 1 1 d . . . H10 H 0.6994 0.3296 -0.2247 0.015 Uiso 1 1 calc R . . C11 C 0.48723(17) 0.4196(2) -0.17326(16) 0.0142(3) Uani 1 1 d . . . H11A H 0.4281 0.4062 -0.2655 0.017 Uiso 1 1 calc R . . H11B H 0.4185 0.3847 -0.1020 0.017 Uiso 1 1 calc R . . C12 C 0.57046(18) 0.0832(2) -0.21585(16) 0.0166(3) Uani 1 1 d . . . H12A H 0.6519 -0.0084 -0.1841 0.020 Uiso 1 1 calc R . . H12B H 0.4770 0.0476 -0.1721 0.020 Uiso 1 1 calc R . . C13 C 0.5369(2) 0.0665(3) -0.37377(17) 0.0236(4) Uani 1 1 d . . . H13A H 0.5053 -0.0631 -0.3981 0.035 Uiso 1 1 calc R . . H13B H 0.6296 0.0978 -0.4182 0.035 Uiso 1 1 calc R . . H13C H 0.4545 0.1542 -0.4062 0.035 Uiso 1 1 calc R . . 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 0.02247(19) 0.02301(18) 0.01363(16) -0.00103(16) -0.00367(12) 0.00015(17) O1 0.0099(5) 0.0120(5) 0.0297(6) -0.0020(4) -0.0006(5) -0.0006(4) N1 0.0083(6) 0.0127(6) 0.0183(6) -0.0008(5) 0.0005(5) 0.0007(5) N2 0.0090(5) 0.0169(7) 0.0124(5) 0.0005(5) -0.0001(4) -0.0003(5) C1 0.0122(7) 0.0138(7) 0.0173(7) -0.0004(6) 0.0023(6) 0.0008(6) C2 0.0122(7) 0.0145(7) 0.0146(7) -0.0003(6) -0.0001(5) 0.0008(6) C3 0.0110(7) 0.0091(7) 0.0152(7) 0.0006(5) -0.0011(5) -0.0004(5) C4 0.0110(7) 0.0104(7) 0.0140(6) 0.0009(5) 0.0003(5) 0.0004(5) C5 0.0109(6) 0.0126(7) 0.0178(6) 0.0013(6) 0.0011(5) -0.0012(6) C6 0.0158(7) 0.0154(6) 0.0156(6) -0.0010(7) 0.0035(5) -0.0003(7) C7 0.0180(7) 0.0128(8) 0.0135(6) 0.0013(6) -0.0022(5) -0.0018(6) C8 0.0105(7) 0.0135(7) 0.0177(7) 0.0018(5) -0.0028(5) -0.0001(5) C9 0.0116(7) 0.0097(6) 0.0158(7) 0.0006(5) 0.0002(6) -0.0011(5) C10 0.0091(6) 0.0145(7) 0.0128(6) 0.0012(6) -0.0013(5) 0.0000(6) C11 0.0094(7) 0.0138(7) 0.0187(7) -0.0009(6) -0.0020(6) -0.0015(6) C12 0.0158(8) 0.0137(7) 0.0197(7) -0.0001(6) -0.0020(6) -0.0010(6) C13 0.0243(9) 0.0228(9) 0.0228(8) -0.0045(7) -0.0026(7) 0.0010(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 Cl1 C7 1.7432(14) . ? O1 C11 1.4218(19) . ? O1 H1O 0.8401 . ? N1 C1 1.3309(19) . ? N1 C9 1.3710(19) . ? N2 C3 1.3570(19) . ? N2 C10 1.4675(16) . ? N2 H2N 0.8801 . ? C1 C2 1.392(2) . ? C1 H1 0.9500 . ? C2 C3 1.395(2) . ? C2 H2 0.9500 . ? C3 C4 1.4484(19) . ? C4 C9 1.416(2) . ? C4 C5 1.418(2) . ? C5 C6 1.3730(18) . ? C5 H5 0.9500 . ? C6 C7 1.405(2) . ? C6 H6 0.9500 . ? C7 C8 1.366(2) . ? C8 C9 1.424(2) . ? C8 H8 0.9500 . ? C10 C11 1.524(2) . ? C10 C12 1.538(2) . ? C10 H10 1.0000 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.530(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 C11 O1 H1O 112.1 . . ? C1 N1 C9 115.76(13) . . ? C3 N2 C10 123.24(12) . . ? C3 N2 H2N 118.0 . . ? C10 N2 H2N 114.2 . . ? N1 C1 C2 125.63(14) . . ? N1 C1 H1 117.2 . . ? C2 C1 H1 117.2 . . ? C1 C2 C3 120.07(13) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? N2 C3 C2 123.44(13) . . ? N2 C3 C4 120.04(13) . . ? C2 C3 C4 116.42(13) . . ? C9 C4 C5 118.74(13) . . ? C9 C4 C3 118.24(13) . . ? C5 C4 C3 122.89(13) . . ? C6 C5 C4 121.33(13) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 119.00(13) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C8 C7 C6 122.01(13) . . ? C8 C7 Cl1 119.52(12) . . ? C6 C7 Cl1 118.47(11) . . ? C7 C8 C9 119.57(13) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? N1 C9 C4 123.85(13) . . ? N1 C9 C8 116.81(13) . . ? C4 C9 C8 119.31(13) . . ? N2 C10 C11 108.62(11) . . ? N2 C10 C12 110.98(12) . . ? C11 C10 C12 111.73(11) . . ? N2 C10 H10 108.5 . . ? C11 C10 H10 108.5 . . ? C12 C10 H10 108.5 . . ? O1 C11 C10 114.50(12) . . ? O1 C11 H11A 108.6 . . ? C10 C11 H11A 108.6 . . ? O1 C11 H11B 108.6 . . ? C10 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C13 C12 C10 114.38(13) . . ? C13 C12 H12A 108.7 . . ? C10 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? C10 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C9 N1 C1 C2 -0.2(2) . . . . ? N1 C1 C2 C3 0.3(2) . . . . ? C10 N2 C3 C2 1.1(2) . . . . ? C10 N2 C3 C4 177.44(13) . . . . ? C1 C2 C3 N2 175.42(14) . . . . ? C1 C2 C3 C4 -1.0(2) . . . . ? N2 C3 C4 C9 -174.99(13) . . . . ? C2 C3 C4 C9 1.56(19) . . . . ? N2 C3 C4 C5 0.9(2) . . . . ? C2 C3 C4 C5 177.44(15) . . . . ? C9 C4 C5 C6 0.7(2) . . . . ? C3 C4 C5 C6 -175.15(16) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? C5 C6 C7 C8 -1.0(3) . . . . ? C5 C6 C7 Cl1 179.16(15) . . . . ? C6 C7 C8 C9 2.1(2) . . . . ? Cl1 C7 C8 C9 -178.01(11) . . . . ? C1 N1 C9 C4 0.9(2) . . . . ? C1 N1 C9 C8 -177.25(13) . . . . ? C5 C4 C9 N1 -177.63(14) . . . . ? C3 C4 C9 N1 -1.6(2) . . . . ? C5 C4 C9 C8 0.4(2) . . . . ? C3 C4 C9 C8 176.50(12) . . . . ? C7 C8 C9 N1 176.38(15) . . . . ? C7 C8 C9 C4 -1.8(2) . . . . ? C3 N2 C10 C11 -150.13(14) . . . . ? C3 N2 C10 C12 86.66(16) . . . . ? N2 C10 C11 O1 69.05(16) . . . . ? C12 C10 C11 O1 -168.20(13) . . . . ? N2 C10 C12 C13 -164.34(13) . . . . ? C11 C10 C12 C13 74.27(16) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.26 _refine_diff_density_min -0.23 _refine_diff_density_rms 0.049