# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email atk@iitg.ernet.in _publ_contact_author_name 'Abu Khan' _publ_author_name 'Abu Khan' # Attachment '- 5n.cif' data_bbb _database_code_depnum_ccdc_archive 'CCDC 837583' #TrackingRef '- 5n.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 Cl3 N3' _chemical_formula_weight 486.85 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9999(9) _cell_length_b 11.9658(10) _cell_length_c 16.7478(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.120(4) _cell_angle_gamma 90.00 _cell_volume 2603.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4426 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 19.44 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.370 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21584 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0614 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.49 _reflns_number_total 4970 _reflns_number_gt 2367 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1165P)^2^+2.2503P] 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 4970 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1786 _refine_ls_R_factor_gt 0.0875 _refine_ls_wR_factor_ref 0.2754 _refine_ls_wR_factor_gt 0.2237 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.46739(14) 0.72381(17) 1.06730(9) 0.1298(8) Uani 1 1 d . . . Cl3 Cl 0.77136(14) 0.1262(3) 0.69875(15) 0.1819(12) Uani 1 1 d . . . N1 N 0.3100(2) 0.5619(3) 0.75189(19) 0.0552(9) Uani 1 1 d . . . N2 N 0.3443(3) 0.2564(3) 0.7596(2) 0.0580(9) Uani 1 1 d . . . H2A H 0.2957 0.2096 0.7482 0.070 Uiso 1 1 calc R . . C13 C 0.3194(3) 0.3627(3) 0.7954(2) 0.0557(11) Uani 1 1 d . . . H13A H 0.3775 0.3839 0.8313 0.067 Uiso 1 1 calc R . . C14 C 0.3021(3) 0.4578(4) 0.7349(2) 0.0534(11) Uani 1 1 d . . . N3 N 0.2756(3) 0.4243(3) 0.6608(2) 0.0655(10) Uani 1 1 d . . . H3A H 0.2643 0.3540 0.6540 0.079 Uiso 1 1 calc R . . C4 C 0.3471(3) 0.5952(3) 0.8288(2) 0.0563(11) Uani 1 1 d . . . C15 C 0.4442(3) 0.2286(4) 0.7433(2) 0.0603(12) Uani 1 1 d . . . Cl2 Cl -0.0461(2) 0.3228(2) 1.00159(19) 0.2154(15) Uani 1 1 d . . . C3 C 0.4506(4) 0.6150(4) 0.8425(3) 0.0744(14) Uani 1 1 d . . . H3B H 0.4958 0.6028 0.8016 0.089 Uiso 1 1 calc R . . C7 C 0.2264(4) 0.3495(4) 0.8455(3) 0.0646(12) Uani 1 1 d . . . C16 C 0.4715(4) 0.1163(4) 0.7372(3) 0.0744(14) Uani 1 1 d . . . H16A H 0.4219 0.0612 0.7432 0.089 Uiso 1 1 calc R . . C6 C 0.3181(4) 0.6566(4) 0.9628(3) 0.0812(15) Uani 1 1 d . . . H6A H 0.2728 0.6706 1.0034 0.097 Uiso 1 1 calc R . . C21 C 0.2640(4) 0.4960(4) 0.5907(2) 0.0663(13) Uani 1 1 d . . . H21A H 0.2804 0.5726 0.6074 0.080 Uiso 1 1 calc R . . C1 C 0.4222(5) 0.6734(4) 0.9758(3) 0.0836(16) Uani 1 1 d . . . C12 C 0.2351(5) 0.3621(4) 0.9277(3) 0.0906(16) Uani 1 1 d . . . H12A H 0.2996 0.3768 0.9513 0.109 Uiso 1 1 calc R . . C8 C 0.1320(4) 0.3263(4) 0.8117(4) 0.0803(15) Uani 1 1 d . . . H8A H 0.1239 0.3176 0.7566 0.096 Uiso 1 1 calc R . . C5 C 0.2812(4) 0.6187(4) 0.8892(3) 0.0692(13) Uani 1 1 d . . . H5A H 0.2107 0.6089 0.8803 0.083 Uiso 1 1 calc R . . C19 C 0.6195(5) 0.2758(7) 0.7199(3) 0.103(2) Uani 1 1 d . . . H19A H 0.6697 0.3303 0.7142 0.123 Uiso 1 1 calc R . . C17 C 0.5706(5) 0.0863(6) 0.7224(4) 0.1011(18) Uani 1 1 d . . . H17A H 0.5874 0.0112 0.7175 0.121 Uiso 1 1 calc R . . C18 C 0.6454(5) 0.1661(8) 0.7147(4) 0.106(2) Uani 1 1 d . . . C20 C 0.5197(4) 0.3075(5) 0.7335(3) 0.0781(14) Uani 1 1 d . . . H20A H 0.5032 0.3830 0.7360 0.094 Uiso 1 1 calc R . . C22 C 0.3402(5) 0.4616(6) 0.5302(4) 0.114(2) Uani 1 1 d . . . H22A H 0.3316 0.3826 0.5187 0.136 Uiso 1 1 calc R . . H22B H 0.4093 0.4726 0.5525 0.136 Uiso 1 1 calc R . . C10 C 0.0608(7) 0.3320(6) 0.9420(6) 0.117(2) Uani 1 1 d . . . C26 C 0.1593(4) 0.4951(6) 0.5574(3) 0.107(2) Uani 1 1 d . . . H26A H 0.1137 0.5267 0.5960 0.128 Uiso 1 1 calc R . . H26B H 0.1382 0.4184 0.5475 0.128 Uiso 1 1 calc R . . C23 C 0.3273(5) 0.5276(7) 0.4527(4) 0.130(3) Uani 1 1 d . . . H23A H 0.3452 0.6052 0.4628 0.156 Uiso 1 1 calc R . . H23B H 0.3743 0.4985 0.4141 0.156 Uiso 1 1 calc R . . C2 C 0.4882(4) 0.6524(5) 0.9155(3) 0.0891(17) Uani 1 1 d . . . H2B H 0.5585 0.6636 0.9241 0.107 Uiso 1 1 calc R . . C9 C 0.0456(5) 0.3154(5) 0.8610(5) 0.108(2) Uani 1 1 d . . . H9A H -0.0192 0.2976 0.8392 0.130 Uiso 1 1 calc R . . C11 C 0.1522(8) 0.3535(6) 0.9756(4) 0.122(2) Uani 1 1 d . . . H11A H 0.1601 0.3627 1.0306 0.146 Uiso 1 1 calc R . . C25 C 0.1483(5) 0.5615(7) 0.4792(4) 0.130(3) Uani 1 1 d . . . H25A H 0.0784 0.5543 0.4575 0.155 Uiso 1 1 calc R . . H25B H 0.1610 0.6399 0.4901 0.155 Uiso 1 1 calc R . . C24 C 0.2214(6) 0.5215(6) 0.4189(3) 0.118(2) Uani 1 1 d . . . H24A H 0.2051 0.4450 0.4041 0.141 Uiso 1 1 calc R . . H24B H 0.2150 0.5674 0.3713 0.141 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 0.1408(15) 0.1670(17) 0.0781(10) -0.0353(10) -0.0427(10) 0.0384(12) Cl3 0.0775(12) 0.282(3) 0.189(2) 0.040(2) 0.0513(13) 0.0535(15) N1 0.057(2) 0.051(2) 0.057(2) 0.0010(17) -0.0013(16) -0.0017(17) N2 0.050(2) 0.050(2) 0.073(2) -0.0031(18) -0.0005(17) -0.0033(17) C13 0.058(3) 0.052(3) 0.057(2) 0.002(2) -0.002(2) -0.001(2) C14 0.045(2) 0.059(3) 0.056(3) 0.004(2) -0.0010(19) -0.001(2) N3 0.087(3) 0.050(2) 0.058(2) 0.0030(18) -0.0145(19) -0.0074(19) C4 0.062(3) 0.050(3) 0.056(3) 0.002(2) -0.002(2) 0.000(2) C15 0.061(3) 0.068(3) 0.053(3) 0.008(2) 0.003(2) 0.001(3) Cl2 0.193(3) 0.207(3) 0.257(3) 0.001(2) 0.160(3) -0.017(2) C3 0.061(3) 0.090(4) 0.072(3) -0.016(3) 0.001(2) -0.002(3) C7 0.072(3) 0.052(3) 0.071(3) 0.005(2) 0.014(3) 0.005(2) C16 0.063(3) 0.075(4) 0.086(3) 0.004(3) 0.009(3) 0.008(3) C6 0.087(4) 0.096(4) 0.061(3) 0.001(3) 0.005(3) 0.014(3) C21 0.088(3) 0.056(3) 0.054(3) 0.002(2) -0.006(2) 0.001(2) C1 0.097(4) 0.087(4) 0.065(3) -0.009(3) -0.016(3) 0.018(3) C12 0.112(5) 0.085(4) 0.077(4) 0.011(3) 0.018(3) 0.007(3) C8 0.066(3) 0.068(3) 0.107(4) -0.005(3) 0.018(3) -0.001(3) C5 0.065(3) 0.078(3) 0.065(3) 0.004(3) 0.001(2) 0.004(2) C19 0.064(4) 0.147(6) 0.097(4) 0.041(4) 0.018(3) -0.013(4) C17 0.083(4) 0.113(5) 0.109(4) 0.002(4) 0.018(3) 0.030(4) C18 0.060(4) 0.160(7) 0.099(4) 0.022(4) 0.028(3) 0.032(4) C20 0.069(3) 0.087(4) 0.079(3) 0.013(3) 0.011(3) -0.007(3) C22 0.084(4) 0.160(6) 0.097(4) 0.029(4) 0.015(3) 0.005(4) C10 0.116(6) 0.095(5) 0.144(7) 0.003(5) 0.069(6) -0.001(4) C26 0.077(4) 0.154(6) 0.089(4) 0.045(4) -0.004(3) 0.008(4) C23 0.110(5) 0.194(8) 0.087(4) 0.046(5) 0.022(4) -0.005(5) C2 0.070(3) 0.114(5) 0.083(4) -0.019(3) -0.014(3) 0.004(3) C9 0.086(4) 0.075(4) 0.164(7) 0.003(4) 0.028(5) -0.007(3) C11 0.150(7) 0.122(6) 0.097(5) 0.013(4) 0.056(5) 0.000(5) C25 0.090(4) 0.183(7) 0.114(5) 0.072(5) -0.016(4) -0.002(5) C24 0.146(6) 0.142(6) 0.064(4) 0.017(4) -0.014(4) -0.036(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 C1 1.730(5) . ? Cl3 C18 1.736(6) . ? N1 C14 1.280(5) . ? N1 C4 1.416(5) . ? N2 C15 1.377(5) . ? N2 C13 1.449(5) . ? C13 C7 1.505(6) . ? C13 C14 1.536(6) . ? C14 N3 1.337(5) . ? N3 C21 1.458(5) . ? C4 C3 1.377(6) . ? C4 C5 1.379(6) . ? C15 C20 1.377(6) . ? C15 C16 1.395(6) . ? Cl2 C10 1.745(7) . ? C3 C2 1.376(6) . ? C7 C8 1.362(7) . ? C7 C12 1.386(7) . ? C16 C17 1.368(7) . ? C6 C1 1.377(7) . ? C6 C5 1.383(6) . ? C21 C26 1.453(7) . ? C21 C22 1.500(7) . ? C1 C2 1.372(7) . ? C12 C11 1.370(9) . ? C8 C9 1.424(8) . ? C19 C18 1.359(9) . ? C19 C20 1.378(8) . ? C17 C18 1.372(9) . ? C22 C23 1.524(8) . ? C10 C11 1.321(10) . ? C10 C9 1.378(10) . ? C26 C25 1.533(7) . ? C23 C24 1.471(8) . ? C25 C24 1.490(9) . ? 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 C14 N1 C4 119.9(3) . . ? C15 N2 C13 121.4(3) . . ? N2 C13 C7 109.6(3) . . ? N2 C13 C14 114.0(3) . . ? C7 C13 C14 110.2(3) . . ? N1 C14 N3 121.0(4) . . ? N1 C14 C13 124.4(4) . . ? N3 C14 C13 114.6(4) . . ? C14 N3 C21 125.9(4) . . ? C3 C4 C5 118.2(4) . . ? C3 C4 N1 119.8(4) . . ? C5 C4 N1 121.7(4) . . ? C20 C15 N2 122.7(4) . . ? C20 C15 C16 117.8(4) . . ? N2 C15 C16 119.5(4) . . ? C2 C3 C4 121.1(5) . . ? C8 C7 C12 118.3(5) . . ? C8 C7 C13 121.3(4) . . ? C12 C7 C13 120.3(5) . . ? C17 C16 C15 120.7(5) . . ? C1 C6 C5 119.6(5) . . ? C26 C21 N3 111.9(4) . . ? C26 C21 C22 111.7(4) . . ? N3 C21 C22 109.4(4) . . ? C2 C1 C6 119.7(5) . . ? C2 C1 Cl1 120.9(5) . . ? C6 C1 Cl1 119.3(5) . . ? C11 C12 C7 122.4(6) . . ? C7 C8 C9 119.7(6) . . ? C4 C5 C6 121.1(4) . . ? C18 C19 C20 120.9(6) . . ? C16 C17 C18 120.7(6) . . ? C19 C18 C17 119.2(5) . . ? C19 C18 Cl3 120.9(6) . . ? C17 C18 Cl3 119.9(6) . . ? C15 C20 C19 120.7(6) . . ? C21 C22 C23 112.3(5) . . ? C11 C10 C9 122.8(7) . . ? C11 C10 Cl2 119.5(8) . . ? C9 C10 Cl2 117.7(7) . . ? C21 C26 C25 112.4(5) . . ? C24 C23 C22 111.9(5) . . ? C1 C2 C3 120.1(5) . . ? C10 C9 C8 118.0(6) . . ? C10 C11 C12 118.7(7) . . ? C24 C25 C26 111.7(6) . . ? C23 C24 C25 109.6(5) . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.594 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.052 # Attachment '- 5b.cif' data_aaa _database_code_depnum_ccdc_archive 'CCDC 838468' #TrackingRef '- 5b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 Br Cl2 N3' _chemical_formula_weight 505.27 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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 13.3588(10) _cell_length_b 10.7992(8) _cell_length_c 16.6412(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2400.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9771 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 23.83 _exptl_crystal_description brick _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 1.950 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29277 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.44 _reflns_number_total 5976 _reflns_number_gt 3986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0332P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 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 0.008(7) _refine_ls_number_reflns 5976 _refine_ls_number_parameters 271 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0770 _refine_ls_wR_factor_gt 0.0665 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.46522(2) 0.37183(3) 0.22155(2) 0.07078(11) Uani 1 1 d . . . Cl1 Cl 1.35860(6) 0.66564(8) 0.14085(6) 0.0822(3) Uani 1 1 d . . . Cl2 Cl 0.65743(6) 0.92354(7) -0.15996(5) 0.0641(2) Uani 1 1 d . . . C1 C 0.6689(2) 0.6878(3) -0.10595(15) 0.0505(6) Uani 1 1 d . . . H1A H 0.5996 0.6914 -0.1009 0.061 Uiso 1 1 calc R . . C2 C 0.7211(2) 0.7887(2) -0.13275(14) 0.0441(6) Uani 1 1 d . . . C3 C 0.8231(2) 0.7846(2) -0.13720(15) 0.0514(7) Uani 1 1 d . . . H3A H 0.8584 0.8542 -0.1539 0.062 Uiso 1 1 calc R . . C4 C 0.8741(2) 0.6779(3) -0.11715(16) 0.0499(6) Uani 1 1 d . . . H4A H 0.9435 0.6762 -0.1206 0.060 Uiso 1 1 calc R . . C5 C 0.82278(19) 0.5727(2) -0.09183(13) 0.0399(5) Uani 1 1 d . . . C6 C 0.7198(2) 0.5801(3) -0.08636(16) 0.0492(6) Uani 1 1 d . . . H6A H 0.6838 0.5114 -0.0691 0.059 Uiso 1 1 calc R . . C7 C 0.6181(2) 0.5266(3) 0.15810(16) 0.0558(7) Uani 1 1 d . . . H7A H 0.5758 0.5914 0.1721 0.067 Uiso 1 1 calc R . . C8 C 0.7095(2) 0.5497(2) 0.12279(17) 0.0504(6) Uani 1 1 d . . . H8A H 0.7287 0.6312 0.1135 0.060 Uiso 1 1 calc R . . C9 C 0.77360(19) 0.4545(2) 0.10082(14) 0.0398(6) Uani 1 1 d . . . C10 C 0.7421(2) 0.3337(2) 0.11570(16) 0.0546(7) Uani 1 1 d . . . H10A H 0.7833 0.2679 0.1012 0.066 Uiso 1 1 calc R . . C11 C 0.6517(2) 0.3100(2) 0.15130(18) 0.0557(7) Uani 1 1 d . . . H11A H 0.6318 0.2289 0.1612 0.067 Uiso 1 1 calc R . . C12 C 0.5908(2) 0.4069(3) 0.17217(15) 0.0485(7) Uani 1 1 d . . . C13 C 1.04525(18) 0.5073(2) 0.13025(14) 0.0418(5) Uani 1 1 d . . . C14 C 1.0936(2) 0.5464(3) 0.06174(16) 0.0595(8) Uani 1 1 d . . . H14A H 1.0612 0.5410 0.0124 0.071 Uiso 1 1 calc R . . C15 C 1.1904(2) 0.5941(3) 0.06548(18) 0.0646(8) Uani 1 1 d . . . H15A H 1.2225 0.6199 0.0188 0.078 Uiso 1 1 calc R . . C16 C 1.2380(2) 0.6030(2) 0.13766(19) 0.0542(7) Uani 1 1 d . . . C17 C 1.1910(2) 0.5667(2) 0.20668(16) 0.0561(7) Uani 1 1 d . . . H17A H 1.2233 0.5744 0.2559 0.067 Uiso 1 1 calc R . . C18 C 1.0960(2) 0.5189(2) 0.20315(14) 0.0523(7) Uani 1 1 d . . . H18A H 1.0647 0.4937 0.2503 0.063 Uiso 1 1 calc R . . C19 C 0.8504(3) 0.1823(3) -0.1111(2) 0.0798(10) Uani 1 1 d . . . H19A H 0.8291 0.2563 -0.1382 0.120 Uiso 1 1 calc R . . H19B H 0.8003 0.1579 -0.0729 0.120 Uiso 1 1 calc R . . H19C H 0.8599 0.1173 -0.1497 0.120 Uiso 1 1 calc R . . C20 C 0.9812(3) 0.0888(3) -0.0247(2) 0.0704(9) Uani 1 1 d . . . H20A H 1.0437 0.1034 0.0021 0.106 Uiso 1 1 calc R . . H20B H 0.9894 0.0235 -0.0633 0.106 Uiso 1 1 calc R . . H20C H 0.9314 0.0654 0.0140 0.106 Uiso 1 1 calc R . . C21 C 1.0289(3) 0.2498(3) -0.1263(2) 0.0857(10) Uani 1 1 d . . . H21A H 1.0074 0.3244 -0.1525 0.129 Uiso 1 1 calc R . . H21B H 1.0404 0.1866 -0.1658 0.129 Uiso 1 1 calc R . . H21C H 1.0898 0.2655 -0.0974 0.129 Uiso 1 1 calc R . . C22 C 0.87722(18) 0.4840(2) 0.06713(14) 0.0407(6) Uani 1 1 d . . . H22A H 0.8811 0.5732 0.0568 0.049 Uiso 1 1 calc R . . C23 C 0.89503(18) 0.4148(2) -0.01251(14) 0.0410(5) Uani 1 1 d . . . C24 C 0.9481(2) 0.2069(2) -0.06773(15) 0.0507(7) Uani 1 1 d . . . N1 N 0.93436(16) 0.30014(18) -0.00428(12) 0.0460(5) Uani 1 1 d . . . H1B H 0.9534 0.2795 0.0432 0.055 Uiso 1 1 calc R . . N2 N 0.87329(17) 0.45980(19) -0.08160(12) 0.0471(5) Uani 1 1 d . . . N3 N 0.95054(16) 0.45237(19) 0.12868(12) 0.0475(5) Uani 1 1 d . . . H3C H 0.9352 0.3987 0.1648 0.057 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 Br1 0.05229(16) 0.0832(2) 0.07682(19) 0.01612(19) 0.01027(18) -0.00406(15) Cl1 0.0506(5) 0.0756(5) 0.1205(7) 0.0244(5) -0.0205(4) -0.0023(4) Cl2 0.0749(5) 0.0545(4) 0.0630(4) 0.0059(3) -0.0091(4) 0.0135(4) C1 0.0363(14) 0.0603(17) 0.0549(16) 0.0036(13) -0.0069(12) -0.0001(13) C2 0.0494(16) 0.0476(15) 0.0353(12) -0.0016(11) -0.0038(11) 0.0043(13) C3 0.0550(18) 0.0451(16) 0.0540(16) 0.0044(12) 0.0065(13) -0.0083(13) C4 0.0382(14) 0.0530(16) 0.0585(16) 0.0003(13) 0.0068(12) -0.0020(12) C5 0.0452(15) 0.0424(13) 0.0319(11) -0.0016(10) -0.0031(10) -0.0013(12) C6 0.0456(16) 0.0483(15) 0.0537(15) 0.0083(12) -0.0022(12) -0.0066(13) C7 0.0552(18) 0.0501(16) 0.0620(17) -0.0064(13) 0.0054(13) 0.0048(13) C8 0.0517(16) 0.0348(14) 0.0646(17) -0.0009(12) 0.0013(13) -0.0020(12) C9 0.0463(15) 0.0368(14) 0.0363(12) -0.0011(10) 0.0024(11) -0.0006(11) C10 0.0627(18) 0.0399(14) 0.0612(17) 0.0017(12) 0.0117(14) 0.0045(13) C11 0.0598(18) 0.0415(15) 0.0657(18) 0.0057(13) 0.0075(14) -0.0073(14) C12 0.0481(17) 0.0566(17) 0.0408(13) 0.0039(12) 0.0041(12) -0.0051(14) C13 0.0525(15) 0.0369(12) 0.0362(11) -0.0005(10) -0.0028(12) 0.0037(11) C14 0.061(2) 0.077(2) 0.0396(14) 0.0128(14) -0.0061(13) -0.0114(16) C15 0.061(2) 0.083(2) 0.0503(16) 0.0195(14) 0.0012(15) -0.0035(16) C16 0.0509(17) 0.0425(15) 0.0691(19) 0.0073(13) -0.0132(15) 0.0057(12) C17 0.0672(19) 0.0569(16) 0.0442(17) -0.0047(12) -0.0162(14) 0.0019(14) C18 0.0621(18) 0.0565(16) 0.0383(15) 0.0001(11) -0.0022(12) -0.0005(14) C19 0.087(2) 0.063(2) 0.089(2) -0.0220(17) -0.0327(19) 0.0069(18) C20 0.097(3) 0.0486(16) 0.0651(19) -0.0089(14) -0.0085(18) 0.0211(17) C21 0.097(3) 0.085(2) 0.076(2) -0.0071(18) 0.0332(19) 0.0129(19) C22 0.0499(16) 0.0345(13) 0.0379(12) 0.0006(10) 0.0001(11) 0.0004(11) C23 0.0407(14) 0.0407(13) 0.0415(13) -0.0021(11) 0.0016(11) 0.0007(11) C24 0.0614(18) 0.0434(15) 0.0473(15) -0.0078(11) -0.0042(12) 0.0072(13) N1 0.0548(13) 0.0457(12) 0.0375(11) -0.0022(9) -0.0022(9) 0.0111(10) N2 0.0564(15) 0.0470(12) 0.0380(11) 0.0002(9) 0.0006(9) 0.0093(10) N3 0.0584(14) 0.0481(12) 0.0359(10) 0.0066(9) -0.0023(10) -0.0083(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 Br1 C12 1.906(3) . ? Cl1 C16 1.748(3) . ? Cl2 C2 1.747(3) . ? C1 C2 1.369(4) . ? C1 C6 1.385(4) . ? C2 C3 1.365(4) . ? C3 C4 1.379(4) . ? C4 C5 1.392(4) . ? C5 C6 1.381(4) . ? C5 N2 1.404(3) . ? C7 C12 1.363(4) . ? C7 C8 1.378(4) . ? C8 C9 1.387(3) . ? C9 C10 1.393(3) . ? C9 C22 1.527(4) . ? C10 C11 1.370(4) . ? C11 C12 1.370(4) . ? C13 C14 1.377(4) . ? C13 C18 1.395(3) . ? C13 N3 1.398(3) . ? C14 C15 1.394(4) . ? C15 C16 1.362(4) . ? C16 C17 1.366(4) . ? C17 C18 1.371(4) . ? C19 C24 1.514(4) . ? C20 C24 1.527(4) . ? C21 C24 1.527(4) . ? C22 N3 1.458(3) . ? C22 C23 1.540(3) . ? C23 N2 1.282(3) . ? C23 N1 1.352(3) . ? C24 N1 1.471(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.6(3) . . ? C3 C2 C1 120.1(2) . . ? C3 C2 Cl2 119.9(2) . . ? C1 C2 Cl2 120.0(2) . . ? C2 C3 C4 120.4(3) . . ? C3 C4 C5 120.8(3) . . ? C6 C5 C4 117.6(2) . . ? C6 C5 N2 121.4(2) . . ? C4 C5 N2 120.6(2) . . ? C5 C6 C1 121.5(3) . . ? C12 C7 C8 118.9(3) . . ? C7 C8 C9 121.6(2) . . ? C8 C9 C10 117.5(2) . . ? C8 C9 C22 120.1(2) . . ? C10 C9 C22 122.3(2) . . ? C11 C10 C9 121.2(2) . . ? C10 C11 C12 119.4(3) . . ? C7 C12 C11 121.4(3) . . ? C7 C12 Br1 119.9(2) . . ? C11 C12 Br1 118.7(2) . . ? C14 C13 C18 117.7(2) . . ? C14 C13 N3 122.6(2) . . ? C18 C13 N3 119.6(2) . . ? C13 C14 C15 120.8(3) . . ? C16 C15 C14 119.9(3) . . ? C15 C16 C17 120.4(3) . . ? C15 C16 Cl1 118.9(2) . . ? C17 C16 Cl1 120.6(2) . . ? C16 C17 C18 119.8(2) . . ? C17 C18 C13 121.4(2) . . ? N3 C22 C9 107.60(19) . . ? N3 C22 C23 112.80(19) . . ? C9 C22 C23 110.80(19) . . ? N2 C23 N1 121.8(2) . . ? N2 C23 C22 123.6(2) . . ? N1 C23 C22 114.6(2) . . ? N1 C24 C19 110.8(2) . . ? N1 C24 C21 109.8(2) . . ? C19 C24 C21 111.0(3) . . ? N1 C24 C20 105.7(2) . . ? C19 C24 C20 109.1(3) . . ? C21 C24 C20 110.3(3) . . ? C23 N1 C24 127.1(2) . . ? C23 N2 C5 123.2(2) . . ? C13 N3 C22 121.5(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.44 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.269 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.042 data_rsb_p2_bn_0m _database_code_depnum_ccdc_archive 'CCDC 855248' #TrackingRef '- 5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H27 N3' _chemical_formula_weight 357.49 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6045(7) _cell_length_b 11.6974(7) _cell_length_c 15.6896(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.044(3) _cell_angle_gamma 90.00 _cell_volume 2082.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.140 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9702 _exptl_absorpt_correction_T_max 0.9833 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20224 _diffrn_reflns_av_R_equivalents 0.1111 _diffrn_reflns_av_sigmaI/netI 0.0617 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3784 _reflns_number_gt 2543 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3784 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1612 _refine_ls_wR_factor_gt 0.1423 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C15 C 0.25879(14) 0.72336(14) 0.02500(10) 0.0460(4) Uani 1 1 d . . . C9 C 0.26911(15) 0.41073(15) 0.01174(10) 0.0471(4) Uani 1 1 d . . . C16 C 0.28688(16) 0.80634(16) -0.03103(12) 0.0565(5) Uani 1 1 d . . . H16 H 0.3381 0.7881 -0.0673 0.068 Uiso 1 1 calc R . . C20 C 0.18430(16) 0.75430(16) 0.07973(12) 0.0576(5) Uani 1 1 d . . . H20 H 0.1658 0.7015 0.1191 0.069 Uiso 1 1 calc R . . C10 C 0.16948(17) 0.37132(18) -0.04390(12) 0.0646(5) Uani 1 1 d . . . H10 H 0.0978 0.4081 -0.0462 0.078 Uiso 1 1 calc R . . C14 C 0.37412(18) 0.35346(17) 0.01344(12) 0.0638(5) Uani 1 1 d . . . H14 H 0.4425 0.3782 0.0510 0.077 Uiso 1 1 calc R . . C13 C 0.3788(2) 0.26035(19) -0.03968(13) 0.0742(6) Uani 1 1 d . . . H13 H 0.4502 0.2233 -0.0377 0.089 Uiso 1 1 calc R . . C19 C 0.13736(19) 0.86373(19) 0.07593(15) 0.0739(6) Uani 1 1 d . . . H19 H 0.0864 0.8834 0.1121 0.089 Uiso 1 1 calc R . . C17 C 0.24042(19) 0.91436(18) -0.03368(15) 0.0714(6) Uani 1 1 d . . . H17 H 0.2602 0.9682 -0.0718 0.086 Uiso 1 1 calc R . . C12 C 0.2797(2) 0.22204(18) -0.09521(13) 0.0709(6) Uani 1 1 d . . . H12 H 0.2834 0.1597 -0.1313 0.085 Uiso 1 1 calc R . . C11 C 0.1750(2) 0.2765(2) -0.09701(14) 0.0770(7) Uani 1 1 d . . . H11 H 0.1069 0.2502 -0.1339 0.092 Uiso 1 1 calc R . . C18 C 0.1656(2) 0.94366(18) 0.01897(16) 0.0792(7) Uani 1 1 d . . . H18 H 0.1338 1.0169 0.0166 0.095 Uiso 1 1 calc R . . C1 C 0.16112(15) 0.42295(16) 0.20248(10) 0.0513(5) Uani 1 1 d . . . C2 C 0.12343(17) 0.31787(18) 0.16535(12) 0.0632(5) Uani 1 1 d . . . H2 H 0.1761 0.2693 0.1461 0.076 Uiso 1 1 calc R . . C6 C 0.08022(17) 0.49194(19) 0.23158(12) 0.0643(5) Uani 1 1 d . . . H6 H 0.1045 0.5621 0.2569 0.077 Uiso 1 1 calc R . . C3 C 0.0057(2) 0.2861(2) 0.15723(14) 0.0795(7) Uani 1 1 d . . . H3 H -0.0203 0.2166 0.1314 0.095 Uiso 1 1 calc R . . C4 C -0.07236(19) 0.3566(3) 0.18712(15) 0.0856(8) Uani 1 1 d . . . H4 H -0.1504 0.3343 0.1822 0.103 Uiso 1 1 calc R . . C5 C -0.03466(19) 0.4589(2) 0.22378(14) 0.0783(7) Uani 1 1 d . . . H5 H -0.0873 0.5067 0.2437 0.094 Uiso 1 1 calc R . . C8 C 0.26259(14) 0.51711(14) 0.06568(10) 0.0441(4) Uani 1 1 d . . . H8 H 0.1794 0.5318 0.0656 0.053 Uiso 1 1 calc R . . C21 C 0.53184(14) 0.51251(15) 0.25802(11) 0.0470(4) Uani 1 1 d . . . C22 C 0.64592(18) 0.5631(2) 0.24298(15) 0.0779(7) Uani 1 1 d . . . H22A H 0.6647 0.5301 0.1915 0.117 Uiso 1 1 calc R . . H22B H 0.7082 0.5470 0.2922 0.117 Uiso 1 1 calc R . . H22C H 0.6373 0.6444 0.2356 0.117 Uiso 1 1 calc R . . C23 C 0.4983(2) 0.5712(2) 0.33591(13) 0.0773(6) Uani 1 1 d . . . H23A H 0.4879 0.6515 0.3244 0.116 Uiso 1 1 calc R . . H23B H 0.5597 0.5599 0.3866 0.116 Uiso 1 1 calc R . . H23C H 0.4261 0.5392 0.3459 0.116 Uiso 1 1 calc R . . C24 C 0.5461(2) 0.38515(18) 0.27406(15) 0.0767(6) Uani 1 1 d . . . H24A H 0.4719 0.3528 0.2794 0.115 Uiso 1 1 calc R . . H24B H 0.6033 0.3720 0.3268 0.115 Uiso 1 1 calc R . . H24C H 0.5720 0.3499 0.2261 0.115 Uiso 1 1 calc R . . C7 C 0.32772(14) 0.50077(13) 0.16110(10) 0.0432(4) Uani 1 1 d . . . N3 N 0.44234(12) 0.53349(12) 0.17769(9) 0.0491(4) Uani 1 1 d . . . H3A H 0.4655 0.5705 0.1370 0.059 Uiso 1 1 calc R . . N1 N 0.28107(12) 0.45532(13) 0.21946(9) 0.0531(4) Uani 1 1 d . . . N2 N 0.30779(12) 0.61454(12) 0.02429(9) 0.0500(4) Uani 1 1 d . . . H2A H 0.3659 0.6045 -0.0011 0.060 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 C15 0.0446(9) 0.0493(11) 0.0423(9) 0.0024(7) 0.0047(7) -0.0037(8) C9 0.0534(11) 0.0510(10) 0.0374(8) 0.0063(7) 0.0105(7) -0.0045(8) C16 0.0565(11) 0.0539(12) 0.0597(11) 0.0110(9) 0.0136(9) -0.0043(9) C20 0.0604(12) 0.0575(13) 0.0566(11) -0.0016(8) 0.0165(9) -0.0018(9) C10 0.0549(12) 0.0812(15) 0.0579(12) -0.0050(10) 0.0122(9) -0.0108(10) C14 0.0602(12) 0.0729(14) 0.0537(11) -0.0091(9) 0.0012(9) 0.0120(10) C13 0.0889(16) 0.0716(14) 0.0584(12) -0.0069(10) 0.0068(11) 0.0191(12) C19 0.0708(14) 0.0684(15) 0.0849(15) -0.0177(11) 0.0216(11) 0.0025(11) C17 0.0732(14) 0.0551(13) 0.0835(15) 0.0160(10) 0.0109(12) -0.0054(11) C12 0.1057(18) 0.0529(12) 0.0557(12) -0.0016(9) 0.0205(12) -0.0087(12) C11 0.0788(16) 0.0865(16) 0.0648(13) -0.0184(11) 0.0126(11) -0.0340(13) C18 0.0761(16) 0.0503(14) 0.1062(19) -0.0037(12) 0.0078(14) 0.0040(11) C1 0.0469(10) 0.0677(12) 0.0393(9) 0.0131(8) 0.0092(7) -0.0081(9) C2 0.0615(12) 0.0723(14) 0.0570(11) 0.0068(9) 0.0153(9) -0.0127(10) C6 0.0547(12) 0.0811(14) 0.0588(11) 0.0072(10) 0.0153(9) -0.0027(10) C3 0.0766(15) 0.0927(18) 0.0651(13) 0.0079(12) 0.0052(11) -0.0367(13) C4 0.0487(13) 0.140(2) 0.0675(14) 0.0194(15) 0.0115(11) -0.0195(14) C5 0.0511(13) 0.115(2) 0.0716(14) 0.0068(13) 0.0185(11) -0.0005(13) C8 0.0404(9) 0.0483(10) 0.0450(9) 0.0088(7) 0.0123(7) 0.0004(7) C21 0.0429(10) 0.0509(11) 0.0465(9) 0.0034(7) 0.0074(7) -0.0018(7) C22 0.0493(12) 0.1050(18) 0.0758(14) 0.0157(12) 0.0049(10) -0.0116(11) C23 0.0845(16) 0.0855(16) 0.0599(12) -0.0153(11) 0.0103(11) -0.0073(12) C24 0.0755(14) 0.0611(14) 0.0867(15) 0.0136(11) 0.0018(11) 0.0082(11) C7 0.0415(10) 0.0451(10) 0.0445(9) 0.0018(7) 0.0122(7) -0.0020(7) N3 0.0431(8) 0.0598(9) 0.0450(8) 0.0089(6) 0.0109(6) -0.0069(7) N1 0.0467(9) 0.0679(10) 0.0457(8) 0.0085(7) 0.0118(7) -0.0110(7) N2 0.0491(8) 0.0516(9) 0.0543(8) 0.0119(6) 0.0224(7) 0.0035(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 C15 C20 1.388(2) . ? C15 C16 1.393(2) . ? C15 N2 1.395(2) . ? C9 C10 1.375(2) . ? C9 C14 1.386(3) . ? C9 C8 1.516(2) . ? C16 C17 1.371(3) . ? C20 C19 1.387(3) . ? C10 C11 1.397(3) . ? C14 C13 1.379(3) . ? C13 C12 1.365(3) . ? C19 C18 1.379(3) . ? C17 C18 1.361(3) . ? C12 C11 1.367(3) . ? C1 C6 1.386(3) . ? C1 C2 1.391(3) . ? C1 N1 1.413(2) . ? C2 C3 1.396(3) . ? C6 C5 1.369(3) . ? C3 C4 1.378(3) . ? C4 C5 1.360(3) . ? C8 N2 1.4621(19) . ? C8 C7 1.542(2) . ? C21 N3 1.477(2) . ? C21 C22 1.513(3) . ? C21 C24 1.514(3) . ? C21 C23 1.521(3) . ? C7 N1 1.273(2) . ? C7 N3 1.356(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 C15 C16 117.82(16) . . ? C20 C15 N2 123.40(15) . . ? C16 C15 N2 118.77(15) . . ? C10 C9 C14 118.01(18) . . ? C10 C9 C8 119.77(16) . . ? C14 C9 C8 122.16(16) . . ? C17 C16 C15 121.26(18) . . ? C19 C20 C15 120.25(18) . . ? C9 C10 C11 120.5(2) . . ? C13 C14 C9 121.02(19) . . ? C12 C13 C14 120.7(2) . . ? C18 C19 C20 120.61(19) . . ? C18 C17 C16 120.7(2) . . ? C13 C12 C11 119.1(2) . . ? C12 C11 C10 120.6(2) . . ? C17 C18 C19 119.4(2) . . ? C6 C1 C2 118.50(17) . . ? C6 C1 N1 119.36(17) . . ? C2 C1 N1 121.80(17) . . ? C1 C2 C3 119.3(2) . . ? C5 C6 C1 121.3(2) . . ? C4 C3 C2 120.7(2) . . ? C5 C4 C3 119.6(2) . . ? C4 C5 C6 120.5(2) . . ? N2 C8 C9 109.12(12) . . ? N2 C8 C7 112.29(13) . . ? C9 C8 C7 111.65(13) . . ? N3 C21 C22 106.52(14) . . ? N3 C21 C24 109.77(15) . . ? C22 C21 C24 110.02(16) . . ? N3 C21 C23 111.00(15) . . ? C22 C21 C23 109.12(16) . . ? C24 C21 C23 110.34(16) . . ? N1 C7 N3 121.80(15) . . ? N1 C7 C8 123.67(15) . . ? N3 C7 C8 114.45(13) . . ? C7 N3 C21 127.15(13) . . ? C7 N1 C1 121.75(14) . . ? C15 N2 C8 121.53(13) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.315 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.064