# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Science # This journal is © The Royal Society of Chemistry and Owner Societies 2011 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ma0405 _database_code_depnum_ccdc_archive 'CCDC 840697' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 N' _chemical_formula_sum 'C17 H21 N' _chemical_formula_weight 239.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall P2ac2ab _chemical_absolute_configuration unk loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.4052(4) _cell_length_b 7.0492(5) _cell_length_c 29.396(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1327.27(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 199 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.069 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.100 -1 0 0 0.130 0 1 0 0.160 0 -1 0 0.160 0 0 1 0.070 0 0 -1 0.170 0 1 -17 0.139 0 1 7 0.086 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ; \f- and \w-rotations with 0.90 \% and 27 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10438 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.10 _reflns_number_total 1674 _reflns_number_gt 1423 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Bruker-Nonius, 2002)' _computing_data_reduction 'EVALCCD (Bruker-Nonius, 2002)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _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^)+(0.0540P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1674 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _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 N1 N 0.1547(3) 0.9382(2) 0.11050(5) 0.0158(4) Uani 1 1 d . . . C1 C 0.1848(3) 1.0915(3) 0.14394(6) 0.0137(4) Uani 1 1 d . . . C2 C 0.3841(3) 1.0444(3) 0.17097(7) 0.0164(5) Uani 1 1 d . . . C3 C 0.4391(3) 1.2098(3) 0.20291(6) 0.0160(5) Uani 1 1 d . . . C4 C 0.4744(3) 1.3908(3) 0.17491(7) 0.0165(5) Uani 1 1 d . . . C5 C 0.2761(3) 1.4395(3) 0.14820(6) 0.0148(4) Uani 1 1 d . . . C6 C 0.2226(3) 1.2739(3) 0.11641(6) 0.0151(5) Uani 1 1 d . . . C7 C 0.0050(3) 1.1260(3) 0.17734(6) 0.0125(4) Uani 1 1 d . . . C8 C 0.0608(3) 1.2909(3) 0.20965(6) 0.0143(4) Uani 1 1 d . . . C9 C 0.0960(3) 1.4721(3) 0.18167(7) 0.0155(5) Uani 1 1 d . . . C10 C 0.2592(3) 1.2416(3) 0.23624(6) 0.0166(5) Uani 1 1 d . . . C11 C -0.0222(3) 0.8589(3) 0.10651(6) 0.0151(4) Uani 1 1 d . . . C12 C -0.0640(3) 0.7107(3) 0.07217(6) 0.0150(5) Uani 1 1 d . . . C13 C 0.0850(3) 0.6566(3) 0.04005(6) 0.0172(5) Uani 1 1 d . . . C14 C 0.0371(3) 0.5180(3) 0.00809(7) 0.0197(5) Uani 1 1 d . . . C15 C -0.1577(4) 0.4329(3) 0.00808(7) 0.0226(5) Uani 1 1 d . . . C16 C -0.3061(4) 0.4855(3) 0.03977(7) 0.0227(5) Uani 1 1 d . . . C17 C -0.2603(3) 0.6240(3) 0.07167(7) 0.0187(5) Uani 1 1 d . . . H2A H 0.358(4) 0.925(3) 0.1878(7) 0.030 Uiso 1 1 d . . . H2B H 0.502(4) 1.016(3) 0.1491(7) 0.030 Uiso 1 1 d . . . H3 H 0.572(4) 1.177(3) 0.2202(7) 0.030 Uiso 1 1 d . . . H4A H 0.517(4) 1.499(3) 0.1973(7) 0.030 Uiso 1 1 d . . . H4B H 0.592(4) 1.378(3) 0.1545(7) 0.030 Uiso 1 1 d . . . H5 H 0.302(4) 1.559(3) 0.1295(7) 0.030 Uiso 1 1 d . . . H6A H 0.337(4) 1.252(3) 0.0950(7) 0.030 Uiso 1 1 d . . . H6B H 0.090(4) 1.305(3) 0.0986(7) 0.030 Uiso 1 1 d . . . H7A H -0.021(4) 1.004(3) 0.1958(7) 0.030 Uiso 1 1 d . . . H7B H -0.129(4) 1.149(3) 0.1599(7) 0.030 Uiso 1 1 d . . . H8 H -0.054(4) 1.314(3) 0.2311(7) 0.030 Uiso 1 1 d . . . H9A H 0.133(4) 1.589(3) 0.2016(7) 0.030 Uiso 1 1 d . . . H9B H -0.035(4) 1.511(3) 0.1660(7) 0.030 Uiso 1 1 d . . . H10A H 0.236(4) 1.121(3) 0.2554(7) 0.030 Uiso 1 1 d . . . H10B H 0.293(4) 1.351(3) 0.2568(7) 0.030 Uiso 1 1 d . . . H11 H -0.148(4) 0.896(3) 0.1254(7) 0.030 Uiso 1 1 d . . . H13 H 0.224(4) 0.721(3) 0.0382(8) 0.030 Uiso 1 1 d . . . H14 H 0.145(4) 0.491(3) -0.0158(7) 0.030 Uiso 1 1 d . . . H15 H -0.194(3) 0.343(3) -0.0139(7) 0.030 Uiso 1 1 d . . . H16 H -0.448(4) 0.426(3) 0.0400(7) 0.030 Uiso 1 1 d . . . H17 H -0.363(4) 0.671(3) 0.0927(7) 0.030 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0177(9) 0.0141(9) 0.0156(8) 0.0001(7) 0.0020(7) 0.0013(7) C1 0.0133(11) 0.0140(10) 0.0138(9) -0.0018(8) 0.0003(8) -0.0005(9) C2 0.0129(11) 0.0157(11) 0.0204(10) 0.0005(9) 0.0014(9) 0.0027(9) C3 0.0125(10) 0.0172(11) 0.0181(10) 0.0016(9) -0.0042(9) -0.0001(9) C4 0.0139(10) 0.0176(11) 0.0180(10) -0.0008(9) -0.0003(9) -0.0036(10) C5 0.0148(10) 0.0144(10) 0.0153(9) 0.0020(8) 0.0016(8) -0.0014(9) C6 0.0148(10) 0.0181(11) 0.0123(9) 0.0011(8) 0.0009(8) -0.0018(9) C7 0.0121(10) 0.0127(10) 0.0126(9) -0.0010(8) 0.0008(9) -0.0006(9) C8 0.0124(10) 0.0166(10) 0.0138(9) -0.0021(9) 0.0037(9) -0.0012(9) C9 0.0149(11) 0.0142(10) 0.0174(10) -0.0013(9) -0.0007(9) 0.0017(9) C10 0.0192(11) 0.0185(11) 0.0122(9) -0.0001(8) -0.0025(8) -0.0016(10) C11 0.0156(11) 0.0148(10) 0.0148(9) 0.0019(8) 0.0002(9) 0.0020(9) C12 0.0192(11) 0.0129(10) 0.0128(8) 0.0035(8) -0.0019(9) 0.0022(9) C13 0.0221(11) 0.0116(11) 0.0180(10) 0.0041(8) 0.0011(9) 0.0005(9) C14 0.0291(12) 0.0153(11) 0.0147(9) 0.0015(8) 0.0010(10) 0.0020(10) C15 0.0375(13) 0.0167(11) 0.0137(9) -0.0001(9) -0.0047(10) -0.0025(11) C16 0.0268(13) 0.0209(11) 0.0204(10) 0.0017(9) -0.0023(10) -0.0097(11) C17 0.0208(11) 0.0192(11) 0.0160(9) 0.0011(8) 0.0017(9) -0.0024(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 N1 C11 1.269(3) . ? N1 C1 1.474(2) . ? C1 C7 1.533(3) . ? C1 C6 1.538(2) . ? C1 C2 1.540(3) . ? C2 C3 1.538(3) . ? C2 H2A 0.99(2) . ? C2 H2B 1.01(2) . ? C3 C10 1.529(3) . ? C3 C4 1.535(3) . ? C3 H3 1.02(2) . ? C4 C5 1.532(3) . ? C4 H4A 1.05(2) . ? C4 H4B 0.97(2) . ? C5 C6 1.534(3) . ? C5 C9 1.534(3) . ? C5 H5 1.02(2) . ? C6 H6A 0.98(2) . ? C6 H6B 1.02(2) . ? C7 C8 1.543(3) . ? C7 H7A 1.03(2) . ? C7 H7B 1.01(2) . ? C8 C10 1.532(3) . ? C8 C9 1.536(3) . ? C8 H8 0.98(2) . ? C9 H9A 1.04(2) . ? C9 H9B 1.00(2) . ? C10 H10A 1.03(2) . ? C10 H10B 1.00(2) . ? C11 C12 1.477(3) . ? C11 H11 1.01(2) . ? C12 C13 1.396(3) . ? C12 C17 1.398(3) . ? C13 C14 1.390(3) . ? C13 H13 1.00(2) . ? C14 C15 1.385(3) . ? C14 H14 1.00(2) . ? C15 C16 1.382(3) . ? C15 H15 0.94(2) . ? C16 C17 1.385(3) . ? C16 H16 1.00(2) . ? C17 H17 0.96(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 C11 N1 C1 120.12(16) . . ? N1 C1 C7 116.42(15) . . ? N1 C1 C6 106.43(13) . . ? C7 C1 C6 108.80(16) . . ? N1 C1 C2 107.14(16) . . ? C7 C1 C2 109.05(15) . . ? C6 C1 C2 108.76(16) . . ? C3 C2 C1 109.95(17) . . ? C3 C2 H2A 112.3(12) . . ? C1 C2 H2A 107.5(13) . . ? C3 C2 H2B 111.4(12) . . ? C1 C2 H2B 109.4(12) . . ? H2A C2 H2B 106.0(17) . . ? C10 C3 C4 109.46(17) . . ? C10 C3 C2 109.23(17) . . ? C4 C3 C2 109.68(15) . . ? C10 C3 H3 110.1(12) . . ? C4 C3 H3 109.5(13) . . ? C2 C3 H3 108.8(13) . . ? C3 C4 C5 109.81(16) . . ? C3 C4 H4A 108.0(11) . . ? C5 C4 H4A 111.9(13) . . ? C3 C4 H4B 111.5(14) . . ? C5 C4 H4B 110.4(13) . . ? H4A C4 H4B 105.0(18) . . ? C6 C5 C4 109.09(17) . . ? C6 C5 C9 109.68(17) . . ? C4 C5 C9 109.18(15) . . ? C6 C5 H5 109.5(11) . . ? C4 C5 H5 109.1(13) . . ? C9 C5 H5 110.3(12) . . ? C5 C6 C1 110.53(14) . . ? C5 C6 H6A 110.1(13) . . ? C1 C6 H6A 109.0(13) . . ? C5 C6 H6B 109.6(13) . . ? C1 C6 H6B 108.4(13) . . ? H6A C6 H6B 109.2(16) . . ? C1 C7 C8 109.86(16) . . ? C1 C7 H7A 109.1(13) . . ? C8 C7 H7A 110.0(11) . . ? C1 C7 H7B 109.6(12) . . ? C8 C7 H7B 113.0(13) . . ? H7A C7 H7B 105.1(18) . . ? C10 C8 C9 109.89(17) . . ? C10 C8 C7 109.58(17) . . ? C9 C8 C7 109.32(15) . . ? C10 C8 H8 109.5(12) . . ? C9 C8 H8 108.3(14) . . ? C7 C8 H8 110.2(13) . . ? C5 C9 C8 109.23(17) . . ? C5 C9 H9A 108.1(13) . . ? C8 C9 H9A 113.2(11) . . ? C5 C9 H9B 112.2(12) . . ? C8 C9 H9B 110.6(13) . . ? H9A C9 H9B 103.4(18) . . ? C3 C10 C8 109.35(14) . . ? C3 C10 H10A 109.7(13) . . ? C8 C10 H10A 110.3(14) . . ? C3 C10 H10B 109.5(13) . . ? C8 C10 H10B 108.3(13) . . ? H10A C10 H10B 109.8(16) . . ? N1 C11 C12 122.44(18) . . ? N1 C11 H11 123.2(11) . . ? C12 C11 H11 114.3(11) . . ? C13 C12 C17 119.24(18) . . ? C13 C12 C11 122.11(18) . . ? C17 C12 C11 118.64(17) . . ? C14 C13 C12 119.9(2) . . ? C14 C13 H13 118.5(13) . . ? C12 C13 H13 121.5(13) . . ? C15 C14 C13 120.24(19) . . ? C15 C14 H14 122.4(12) . . ? C13 C14 H14 117.3(12) . . ? C16 C15 C14 120.23(19) . . ? C16 C15 H15 118.5(13) . . ? C14 C15 H15 121.2(13) . . ? C15 C16 C17 120.0(2) . . ? C15 C16 H16 121.0(12) . . ? C17 C16 H16 119.0(12) . . ? C16 C17 C12 120.40(19) . . ? C16 C17 H17 122.2(13) . . ? C12 C17 H17 117.2(13) . . ? 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 N1 C1 C7 8.9(2) . . . . ? C11 N1 C1 C6 -112.54(19) . . . . ? C11 N1 C1 C2 131.24(19) . . . . ? N1 C1 C2 C3 173.65(15) . . . . ? C7 C1 C2 C3 -59.5(2) . . . . ? C6 C1 C2 C3 59.0(2) . . . . ? C1 C2 C3 C10 60.4(2) . . . . ? C1 C2 C3 C4 -59.5(2) . . . . ? C10 C3 C4 C5 -60.1(2) . . . . ? C2 C3 C4 C5 59.7(2) . . . . ? C3 C4 C5 C6 -59.6(2) . . . . ? C3 C4 C5 C9 60.2(2) . . . . ? C4 C5 C6 C1 60.1(2) . . . . ? C9 C5 C6 C1 -59.4(2) . . . . ? N1 C1 C6 C5 -174.75(16) . . . . ? C7 C1 C6 C5 59.1(2) . . . . ? C2 C1 C6 C5 -59.6(2) . . . . ? N1 C1 C7 C8 -179.69(14) . . . . ? C6 C1 C7 C8 -59.50(19) . . . . ? C2 C1 C7 C8 59.0(2) . . . . ? C1 C7 C8 C10 -59.8(2) . . . . ? C1 C7 C8 C9 60.7(2) . . . . ? C6 C5 C9 C8 59.6(2) . . . . ? C4 C5 C9 C8 -59.9(2) . . . . ? C10 C8 C9 C5 60.1(2) . . . . ? C7 C8 C9 C5 -60.2(2) . . . . ? C4 C3 C10 C8 59.6(2) . . . . ? C2 C3 C10 C8 -60.5(2) . . . . ? C9 C8 C10 C3 -59.9(2) . . . . ? C7 C8 C10 C3 60.3(2) . . . . ? C1 N1 C11 C12 177.13(16) . . . . ? N1 C11 C12 C13 -4.0(3) . . . . ? N1 C11 C12 C17 176.76(19) . . . . ? C17 C12 C13 C14 0.0(3) . . . . ? C11 C12 C13 C14 -179.22(16) . . . . ? C12 C13 C14 C15 -0.2(3) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C14 C15 C16 C17 0.0(3) . . . . ? C15 C16 C17 C12 -0.2(3) . . . . ? C13 C12 C17 C16 0.2(3) . . . . ? C11 C12 C17 C16 179.47(19) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.180 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.055 data_ma0403 _database_code_depnum_ccdc_archive 'CCDC 840698' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H20 F N' _chemical_formula_sum 'C17 H20 F N' _chemical_formula_weight 257.34 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall -P2ybc 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 6.4759(5) _cell_length_b 33.280(2) _cell_length_c 6.8092(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.291(6) _cell_angle_gamma 90.00 _cell_volume 1315.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 86 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.085 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.110 -1 0 0 0.110 0 1 0 0.020 0 -1 0 0.060 0 0 1 0.120 0 0 -1 0.130 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ; \w-rotations with 0.80 \% and 32 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21697 _diffrn_reflns_av_R_equivalents 0.1045 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.96 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2630 _reflns_number_gt 1941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Bruker-Nonius, 2002)' _computing_data_reduction 'EVALCCD (Bruker-Nonius, 2002)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _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^)+(0.0439P)^2^+0.5235P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2630 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 F1 F 0.54561(18) 0.14934(3) 0.94876(16) 0.0217(3) Uani 1 1 d . . . N1 N 0.2508(2) 0.33330(4) 0.8293(2) 0.0143(3) Uani 1 1 d . . . C1 C 0.2297(3) 0.37735(5) 0.8288(3) 0.0135(4) Uani 1 1 d . . . C2 C 0.1102(3) 0.39108(5) 0.5885(3) 0.0164(4) Uani 1 1 d . . . C3 C 0.0582(3) 0.43631(5) 0.5762(3) 0.0173(4) Uani 1 1 d . . . C4 C -0.1013(3) 0.44467(5) 0.6834(3) 0.0185(4) Uani 1 1 d . . . C5 C 0.0175(3) 0.43167(5) 0.9243(3) 0.0168(4) Uani 1 1 d . . . C6 C 0.0703(3) 0.38656(5) 0.9369(3) 0.0161(4) Uani 1 1 d . . . C7 C 0.4540(3) 0.40108(5) 0.9471(3) 0.0157(4) Uani 1 1 d . . . C8 C 0.4009(3) 0.44636(5) 0.9359(3) 0.0175(4) Uani 1 1 d . . . C9 C 0.2430(3) 0.45484(5) 1.0441(3) 0.0190(4) Uani 1 1 d . . . C10 C 0.2823(3) 0.45963(5) 0.6963(3) 0.0194(4) Uani 1 1 d . . . C11 C 0.4462(3) 0.31643(5) 0.9103(3) 0.0141(4) Uani 1 1 d . . . C12 C 0.4700(3) 0.27216(5) 0.9172(3) 0.0132(4) Uani 1 1 d . . . C13 C 0.2806(3) 0.24724(5) 0.8709(3) 0.0138(4) Uani 1 1 d . . . C14 C 0.3050(3) 0.20587(5) 0.8788(3) 0.0152(4) Uani 1 1 d . . . C15 C 0.5204(3) 0.19023(5) 0.9367(3) 0.0147(4) Uani 1 1 d . . . C16 C 0.7121(3) 0.21337(5) 0.9855(3) 0.0160(4) Uani 1 1 d . . . C17 C 0.6843(3) 0.25497(5) 0.9743(3) 0.0150(4) Uani 1 1 d . . . H3 H -0.023(3) 0.4443(6) 0.420(3) 0.030 Uiso 1 1 d . . . H2A H -0.032(4) 0.3757(6) 0.509(3) 0.030 Uiso 1 1 d . . . H2B H 0.215(3) 0.3850(6) 0.519(3) 0.030 Uiso 1 1 d . . . H4A H -0.250(3) 0.4299(6) 0.610(3) 0.030 Uiso 1 1 d . . . H4B H -0.137(3) 0.4736(6) 0.677(3) 0.030 Uiso 1 1 d . . . H5 H -0.083(3) 0.4369(6) 0.993(3) 0.030 Uiso 1 1 d . . . H6A H -0.076(4) 0.3709(6) 0.859(3) 0.030 Uiso 1 1 d . . . H6B H 0.145(3) 0.3778(6) 1.094(3) 0.030 Uiso 1 1 d . . . H7A H 0.535(3) 0.3922(6) 1.103(3) 0.030 Uiso 1 1 d . . . H7B H 0.561(3) 0.3955(6) 0.877(3) 0.030 Uiso 1 1 d . . . H8 H 0.551(3) 0.4618(6) 1.014(3) 0.030 Uiso 1 1 d . . . H9A H 0.318(3) 0.4466(6) 1.200(3) 0.030 Uiso 1 1 d . . . H9B H 0.212(3) 0.4843(6) 1.042(3) 0.030 Uiso 1 1 d . . . H10A H 0.385(3) 0.4551(6) 0.625(3) 0.030 Uiso 1 1 d . . . H10B H 0.251(3) 0.4888(6) 0.690(3) 0.030 Uiso 1 1 d . . . H11 H 0.592(3) 0.3312(6) 0.973(3) 0.030 Uiso 1 1 d . . . H13 H 0.131(4) 0.2587(6) 0.834(3) 0.030 Uiso 1 1 d . . . H14 H 0.178(3) 0.1874(6) 0.851(3) 0.030 Uiso 1 1 d . . . H16 H 0.862(4) 0.2017(6) 1.026(3) 0.030 Uiso 1 1 d . . . H17 H 0.819(4) 0.2724(6) 1.011(3) 0.030 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0283(7) 0.0093(5) 0.0281(6) 0.0011(4) 0.0131(5) 0.0030(4) N1 0.0185(8) 0.0112(7) 0.0141(8) 0.0000(6) 0.0080(7) 0.0003(6) C1 0.0151(9) 0.0098(8) 0.0175(10) -0.0002(6) 0.0088(8) 0.0013(6) C2 0.0209(11) 0.0136(8) 0.0161(10) -0.0012(7) 0.0094(9) 0.0020(7) C3 0.0244(11) 0.0128(8) 0.0154(10) 0.0035(7) 0.0094(9) 0.0052(7) C4 0.0201(11) 0.0116(8) 0.0250(11) 0.0006(7) 0.0111(9) 0.0037(7) C5 0.0202(10) 0.0153(9) 0.0215(10) -0.0004(7) 0.0153(9) 0.0010(7) C6 0.0178(10) 0.0151(9) 0.0174(10) 0.0007(7) 0.0097(9) -0.0008(7) C7 0.0164(10) 0.0120(8) 0.0202(10) 0.0003(7) 0.0094(9) 0.0006(7) C8 0.0196(10) 0.0107(8) 0.0245(11) -0.0023(7) 0.0117(9) -0.0020(7) C9 0.0258(11) 0.0122(9) 0.0211(11) -0.0020(7) 0.0121(9) 0.0015(7) C10 0.0273(11) 0.0122(9) 0.0268(11) 0.0031(7) 0.0194(9) 0.0039(8) C11 0.0189(10) 0.0137(8) 0.0115(9) -0.0013(6) 0.0082(8) -0.0008(7) C12 0.0192(10) 0.0136(9) 0.0075(9) 0.0010(6) 0.0066(8) 0.0024(7) C13 0.0161(10) 0.0156(9) 0.0106(9) 0.0016(7) 0.0067(8) 0.0026(7) C14 0.0206(10) 0.0145(8) 0.0116(9) -0.0003(7) 0.0081(8) -0.0022(7) C15 0.0245(10) 0.0087(8) 0.0122(9) 0.0005(6) 0.0092(8) 0.0030(7) C16 0.0185(10) 0.0164(9) 0.0139(10) 0.0010(7) 0.0078(8) 0.0045(7) C17 0.0182(10) 0.0154(9) 0.0123(9) -0.0009(7) 0.0075(8) -0.0015(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 F1 C15 1.3687(18) . ? N1 C11 1.265(2) . ? N1 C1 1.4721(19) . ? C1 C7 1.532(2) . ? C1 C2 1.538(2) . ? C1 C6 1.540(2) . ? C2 C3 1.537(2) . ? C2 H2A 0.98(2) . ? C2 H2B 1.01(2) . ? C3 C10 1.525(3) . ? C3 C4 1.532(2) . ? C3 H3 0.99(2) . ? C4 C5 1.533(2) . ? C4 H4A 1.00(2) . ? C4 H4B 0.99(2) . ? C5 C9 1.529(2) . ? C5 C6 1.534(2) . ? C5 H5 0.97(2) . ? C6 H6A 1.00(2) . ? C6 H6B 1.00(2) . ? C7 C8 1.540(2) . ? C7 H7A 1.00(2) . ? C7 H7B 1.01(2) . ? C8 C10 1.528(3) . ? C8 C9 1.528(3) . ? C8 H8 1.02(2) . ? C9 H9A 0.99(2) . ? C9 H9B 1.00(2) . ? C10 H10A 0.99(2) . ? C10 H10B 0.99(2) . ? C11 C12 1.480(2) . ? C11 H11 0.98(2) . ? C12 C17 1.388(2) . ? C12 C13 1.396(2) . ? C13 C14 1.384(2) . ? C13 H13 0.97(2) . ? C14 C15 1.373(2) . ? C14 H14 0.98(2) . ? C15 C16 1.371(2) . ? C16 C17 1.394(2) . ? C16 H16 0.97(2) . ? C17 H17 0.98(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 C11 N1 C1 121.11(14) . . ? N1 C1 C7 116.53(14) . . ? N1 C1 C2 107.51(13) . . ? C7 C1 C2 108.61(14) . . ? N1 C1 C6 106.16(13) . . ? C7 C1 C6 109.05(14) . . ? C2 C1 C6 108.76(14) . . ? C3 C2 C1 110.12(14) . . ? C3 C2 H2A 110.7(11) . . ? C1 C2 H2A 109.9(12) . . ? C3 C2 H2B 110.3(11) . . ? C1 C2 H2B 108.4(11) . . ? H2A C2 H2B 107.4(16) . . ? C10 C3 C4 109.54(15) . . ? C10 C3 C2 109.61(15) . . ? C4 C3 C2 109.24(14) . . ? C10 C3 H3 111.5(11) . . ? C4 C3 H3 108.3(11) . . ? C2 C3 H3 108.6(11) . . ? C3 C4 C5 109.49(15) . . ? C3 C4 H4A 112.3(11) . . ? C5 C4 H4A 108.2(11) . . ? C3 C4 H4B 110.6(11) . . ? C5 C4 H4B 108.7(11) . . ? H4A C4 H4B 107.5(16) . . ? C9 C5 C4 109.68(15) . . ? C9 C5 C6 109.12(15) . . ? C4 C5 C6 109.26(14) . . ? C9 C5 H5 109.8(12) . . ? C4 C5 H5 109.8(12) . . ? C6 C5 H5 109.2(11) . . ? C5 C6 C1 110.37(14) . . ? C5 C6 H6A 110.2(11) . . ? C1 C6 H6A 108.7(11) . . ? C5 C6 H6B 109.6(11) . . ? C1 C6 H6B 110.0(11) . . ? H6A C6 H6B 107.9(15) . . ? C1 C7 C8 109.85(14) . . ? C1 C7 H7A 109.6(11) . . ? C8 C7 H7A 110.0(11) . . ? C1 C7 H7B 110.1(11) . . ? C8 C7 H7B 109.8(11) . . ? H7A C7 H7B 107.5(16) . . ? C10 C8 C9 109.52(15) . . ? C10 C8 C7 109.34(14) . . ? C9 C8 C7 109.83(14) . . ? C10 C8 H8 108.9(11) . . ? C9 C8 H8 110.1(11) . . ? C7 C8 H8 109.1(11) . . ? C8 C9 C5 109.53(14) . . ? C8 C9 H9A 110.7(12) . . ? C5 C9 H9A 109.2(11) . . ? C8 C9 H9B 110.3(11) . . ? C5 C9 H9B 110.3(11) . . ? H9A C9 H9B 106.8(15) . . ? C3 C10 C8 109.54(14) . . ? C3 C10 H10A 110.2(11) . . ? C8 C10 H10A 110.3(11) . . ? C3 C10 H10B 110.3(11) . . ? C8 C10 H10B 109.2(11) . . ? H10A C10 H10B 107.2(15) . . ? N1 C11 C12 121.69(16) . . ? N1 C11 H11 123.6(11) . . ? C12 C11 H11 114.7(11) . . ? C17 C12 C13 119.18(15) . . ? C17 C12 C11 119.76(15) . . ? C13 C12 C11 121.05(15) . . ? C14 C13 C12 120.60(16) . . ? C14 C13 H13 119.2(11) . . ? C12 C13 H13 120.2(11) . . ? C15 C14 C13 118.14(16) . . ? C15 C14 H14 118.7(12) . . ? C13 C14 H14 123.2(12) . . ? F1 C15 C16 118.22(15) . . ? F1 C15 C14 118.23(15) . . ? C16 C15 C14 123.55(15) . . ? C15 C16 C17 117.63(17) . . ? C15 C16 H16 122.2(11) . . ? C17 C16 H16 120.2(11) . . ? C12 C17 C16 120.90(17) . . ? C12 C17 H17 119.5(11) . . ? C16 C17 H17 119.6(11) . . ? 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 N1 C1 C7 -4.8(2) . . . . ? C11 N1 C1 C2 117.33(17) . . . . ? C11 N1 C1 C6 -126.41(16) . . . . ? N1 C1 C2 C3 173.65(14) . . . . ? C7 C1 C2 C3 -59.45(18) . . . . ? C6 C1 C2 C3 59.10(18) . . . . ? C1 C2 C3 C10 59.74(19) . . . . ? C1 C2 C3 C4 -60.29(19) . . . . ? C10 C3 C4 C5 -59.61(18) . . . . ? C2 C3 C4 C5 60.46(19) . . . . ? C3 C4 C5 C9 59.33(18) . . . . ? C3 C4 C5 C6 -60.23(18) . . . . ? C9 C5 C6 C1 -60.04(19) . . . . ? C4 C5 C6 C1 59.86(19) . . . . ? N1 C1 C6 C5 -174.43(14) . . . . ? C7 C1 C6 C5 59.26(18) . . . . ? C2 C1 C6 C5 -59.01(18) . . . . ? N1 C1 C7 C8 -178.65(14) . . . . ? C2 C1 C7 C8 59.83(18) . . . . ? C6 C1 C7 C8 -58.55(18) . . . . ? C1 C7 C8 C10 -60.59(19) . . . . ? C1 C7 C8 C9 59.60(19) . . . . ? C10 C8 C9 C5 59.93(18) . . . . ? C7 C8 C9 C5 -60.16(19) . . . . ? C4 C5 C9 C8 -59.52(18) . . . . ? C6 C5 C9 C8 60.12(19) . . . . ? C4 C3 C10 C8 60.15(18) . . . . ? C2 C3 C10 C8 -59.70(18) . . . . ? C9 C8 C10 C3 -60.31(18) . . . . ? C7 C8 C10 C3 60.08(19) . . . . ? C1 N1 C11 C12 178.36(14) . . . . ? N1 C11 C12 C17 169.62(16) . . . . ? N1 C11 C12 C13 -11.5(2) . . . . ? C17 C12 C13 C14 -0.8(2) . . . . ? C11 C12 C13 C14 -179.67(15) . . . . ? C12 C13 C14 C15 1.0(2) . . . . ? C13 C14 C15 F1 178.76(14) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? F1 C15 C16 C17 -179.48(14) . . . . ? C14 C15 C16 C17 -0.3(3) . . . . ? C13 C12 C17 C16 0.1(2) . . . . ? C11 C12 C17 C16 178.94(15) . . . . ? C15 C16 C17 C12 0.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.242 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.046 data_ma0401 _database_code_depnum_ccdc_archive 'CCDC 840699' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H20 Cl N' _chemical_formula_sum 'C17 H20 Cl N' _chemical_formula_weight 273.79 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 C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.270(3) _cell_length_b 6.4963(3) _cell_length_c 16.418(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.590(8) _cell_angle_gamma 90.00 _cell_volume 2772.5(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 115 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.944 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS, Bruker-Nonius, 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ; \f- and \w-rotations with 2.00 \% and 120 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34135 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.90 _diffrn_reflns_theta_max 27.88 _reflns_number_total 3304 _reflns_number_gt 2863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Bruker-Nonius, 2002)' _computing_data_reduction 'EVALCCD (Bruker-Nonius, 2002)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _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^)+(0.0412P)^2^+2.9869P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3304 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.636985(11) 0.54371(5) 0.53989(2) 0.02001(10) Uani 1 1 d . . . N1 N 0.42325(4) 0.88757(16) 0.62361(6) 0.0138(2) Uani 1 1 d . . . C1 C 0.37600(4) 0.91980(17) 0.64804(7) 0.0115(2) Uani 1 1 d . . . C2 C 0.38387(5) 1.12082(19) 0.70030(8) 0.0142(2) Uani 1 1 d . . . C3 C 0.33448(5) 1.17770(19) 0.72202(8) 0.0144(2) Uani 1 1 d . . . C4 C 0.29040(5) 1.20784(19) 0.63851(8) 0.0155(2) Uani 1 1 d . . . C5 C 0.28173(5) 1.00722(19) 0.58663(8) 0.0145(2) Uani 1 1 d . . . C6 C 0.33120(5) 0.95036(19) 0.56512(7) 0.0142(2) Uani 1 1 d . . . C7 C 0.36171(4) 0.74674(18) 0.70042(8) 0.0127(2) Uani 1 1 d . . . C8 C 0.31231(4) 0.80314(19) 0.72222(8) 0.0143(2) Uani 1 1 d . . . C9 C 0.26792(5) 0.83353(19) 0.63929(8) 0.0158(2) Uani 1 1 d . . . C10 C 0.32061(5) 1.00305(19) 0.77428(8) 0.0158(2) Uani 1 1 d . . . C11 C 0.44807(4) 0.71988(19) 0.64274(7) 0.0131(2) Uani 1 1 d . . . C12 C 0.49540(4) 0.67990(18) 0.61883(7) 0.0127(2) Uani 1 1 d . . . C13 C 0.51916(4) 0.83605(19) 0.58566(7) 0.0133(2) Uani 1 1 d . . . C14 C 0.56226(4) 0.79519(19) 0.55999(7) 0.0137(2) Uani 1 1 d . . . C15 C 0.58201(4) 0.59584(19) 0.56938(7) 0.0136(2) Uani 1 1 d . . . C16 C 0.55952(5) 0.43810(19) 0.60252(8) 0.0151(2) Uani 1 1 d . . . C17 C 0.51600(5) 0.48155(19) 0.62726(8) 0.0146(2) Uani 1 1 d . . . H2A H 0.4133(7) 1.101(3) 0.7529(11) 0.030 Uiso 1 1 d . . . H2B H 0.3932(6) 1.230(3) 0.6668(11) 0.030 Uiso 1 1 d . . . H3 H 0.3401(6) 1.303(3) 0.7566(11) 0.030 Uiso 1 1 d . . . H4A H 0.2588(7) 1.247(3) 0.6513(11) 0.030 Uiso 1 1 d . . . H4B H 0.2992(6) 1.324(3) 0.6046(11) 0.030 Uiso 1 1 d . . . H5 H 0.2536(7) 1.031(3) 0.5327(11) 0.030 Uiso 1 1 d . . . H6A H 0.3257(6) 0.825(3) 0.5291(11) 0.030 Uiso 1 1 d . . . H6B H 0.3401(7) 1.060(3) 0.5309(11) 0.030 Uiso 1 1 d . . . H7A H 0.3563(7) 0.618(3) 0.6668(11) 0.030 Uiso 1 1 d . . . H7B H 0.3905(7) 0.724(3) 0.7547(11) 0.030 Uiso 1 1 d . . . H8 H 0.3030(7) 0.690(3) 0.7562(11) 0.030 Uiso 1 1 d . . . H9A H 0.2373(7) 0.871(3) 0.6534(11) 0.030 Uiso 1 1 d . . . H9B H 0.2611(6) 0.703(3) 0.6056(11) 0.030 Uiso 1 1 d . . . H10A H 0.2896(7) 1.039(3) 0.7902(11) 0.030 Uiso 1 1 d . . . H10B H 0.3477(7) 0.982(3) 0.8277(12) 0.030 Uiso 1 1 d . . . H11 H 0.4368(6) 0.608(3) 0.6731(11) 0.030 Uiso 1 1 d . . . H13 H 0.5044(7) 0.974(3) 0.5798(11) 0.030 Uiso 1 1 d . . . H14 H 0.5773(7) 0.898(3) 0.5339(11) 0.030 Uiso 1 1 d . . . H16 H 0.5745(6) 0.300(3) 0.6086(11) 0.030 Uiso 1 1 d . . . H17 H 0.4994(6) 0.373(3) 0.6479(11) 0.030 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01597(15) 0.02171(17) 0.02531(17) -0.00053(12) 0.01069(12) 0.00489(11) N1 0.0119(5) 0.0155(5) 0.0148(5) 0.0000(4) 0.0053(4) 0.0001(4) C1 0.0105(5) 0.0106(5) 0.0137(5) 0.0009(4) 0.0043(4) 0.0009(4) C2 0.0127(5) 0.0114(5) 0.0184(6) -0.0013(5) 0.0047(4) -0.0007(4) C3 0.0156(6) 0.0114(5) 0.0164(6) -0.0019(4) 0.0052(4) 0.0016(4) C4 0.0154(6) 0.0124(6) 0.0195(6) 0.0030(5) 0.0063(5) 0.0040(5) C5 0.0127(5) 0.0152(6) 0.0145(6) 0.0015(4) 0.0026(4) 0.0027(4) C6 0.0143(6) 0.0153(6) 0.0127(5) 0.0009(5) 0.0038(4) 0.0028(4) C7 0.0122(5) 0.0114(5) 0.0150(5) 0.0017(4) 0.0050(4) 0.0016(4) C8 0.0134(5) 0.0129(5) 0.0184(6) 0.0040(5) 0.0077(4) 0.0016(4) C9 0.0119(6) 0.0139(6) 0.0218(6) 0.0001(5) 0.0054(5) -0.0001(4) C10 0.0162(6) 0.0176(6) 0.0151(6) 0.0016(5) 0.0069(5) 0.0043(5) C11 0.0123(5) 0.0147(6) 0.0121(5) -0.0003(4) 0.0035(4) -0.0006(4) C12 0.0111(5) 0.0147(6) 0.0112(5) -0.0011(4) 0.0017(4) 0.0006(4) C13 0.0124(5) 0.0135(6) 0.0127(5) -0.0001(4) 0.0019(4) 0.0020(4) C14 0.0126(5) 0.0156(6) 0.0122(5) 0.0002(4) 0.0027(4) -0.0002(4) C15 0.0101(5) 0.0187(6) 0.0118(5) -0.0027(4) 0.0029(4) 0.0026(4) C16 0.0159(6) 0.0130(6) 0.0150(5) -0.0011(4) 0.0027(4) 0.0030(5) C17 0.0146(6) 0.0139(6) 0.0148(5) 0.0009(4) 0.0035(4) -0.0001(4) _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 C15 1.7422(12) . ? N1 C11 1.2709(16) . ? N1 C1 1.4754(14) . ? C1 C7 1.5357(16) . ? C1 C2 1.5416(16) . ? C1 C6 1.5428(16) . ? C2 C3 1.5387(16) . ? C2 H2A 0.994(18) . ? C2 H2B 0.977(18) . ? C3 C10 1.5370(17) . ? C3 C4 1.5385(17) . ? C3 H3 0.978(18) . ? C4 C5 1.5357(17) . ? C4 H4A 0.981(17) . ? C4 H4B 1.007(18) . ? C5 C9 1.5360(17) . ? C5 C6 1.5391(16) . ? C5 H5 0.993(18) . ? C6 H6A 0.992(18) . ? C6 H6B 0.983(18) . ? C7 C8 1.5391(16) . ? C7 H7A 0.991(18) . ? C7 H7B 1.004(17) . ? C8 C10 1.5335(17) . ? C8 C9 1.5368(17) . ? C8 H8 0.999(18) . ? C9 H9A 0.964(17) . ? C9 H9B 0.999(18) . ? C10 H10A 0.987(18) . ? C10 H10B 0.969(18) . ? C11 C12 1.4811(16) . ? C11 H11 0.983(18) . ? C12 C17 1.3957(17) . ? C12 C13 1.3995(17) . ? C13 C14 1.3888(16) . ? C13 H13 0.974(18) . ? C14 C15 1.3931(17) . ? C14 H14 0.952(18) . ? C15 C16 1.3870(18) . ? C16 C17 1.3946(17) . ? C16 H16 0.975(18) . ? C17 H17 0.953(18) . ? 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 N1 C1 119.87(10) . . ? N1 C1 C7 116.02(9) . . ? N1 C1 C2 106.59(9) . . ? C7 C1 C2 108.94(10) . . ? N1 C1 C6 107.58(9) . . ? C7 C1 C6 108.73(9) . . ? C2 C1 C6 108.79(9) . . ? C3 C2 C1 110.38(9) . . ? C3 C2 H2A 111.2(10) . . ? C1 C2 H2A 108.3(10) . . ? C3 C2 H2B 110.5(10) . . ? C1 C2 H2B 108.5(10) . . ? H2A C2 H2B 107.7(14) . . ? C10 C3 C4 109.49(10) . . ? C10 C3 C2 109.41(10) . . ? C4 C3 C2 109.07(10) . . ? C10 C3 H3 108.2(10) . . ? C4 C3 H3 110.8(10) . . ? C2 C3 H3 109.8(10) . . ? C5 C4 C3 109.52(10) . . ? C5 C4 H4A 109.9(10) . . ? C3 C4 H4A 110.0(10) . . ? C5 C4 H4B 110.5(10) . . ? C3 C4 H4B 109.5(10) . . ? H4A C4 H4B 107.4(14) . . ? C4 C5 C9 109.52(10) . . ? C4 C5 C6 109.41(10) . . ? C9 C5 C6 109.50(10) . . ? C4 C5 H5 108.1(10) . . ? C9 C5 H5 111.2(10) . . ? C6 C5 H5 109.1(10) . . ? C5 C6 C1 110.10(9) . . ? C5 C6 H6A 110.5(10) . . ? C1 C6 H6A 110.9(10) . . ? C5 C6 H6B 110.0(10) . . ? C1 C6 H6B 109.3(10) . . ? H6A C6 H6B 106.0(14) . . ? C1 C7 C8 110.13(9) . . ? C1 C7 H7A 109.2(10) . . ? C8 C7 H7A 109.7(10) . . ? C1 C7 H7B 109.9(10) . . ? C8 C7 H7B 109.4(10) . . ? H7A C7 H7B 108.5(14) . . ? C10 C8 C9 109.22(10) . . ? C10 C8 C7 109.82(10) . . ? C9 C8 C7 109.57(10) . . ? C10 C8 H8 109.3(10) . . ? C9 C8 H8 109.0(10) . . ? C7 C8 H8 110.0(10) . . ? C5 C9 C8 109.37(10) . . ? C5 C9 H9A 109.2(11) . . ? C8 C9 H9A 109.1(10) . . ? C5 C9 H9B 110.5(10) . . ? C8 C9 H9B 110.2(10) . . ? H9A C9 H9B 108.4(14) . . ? C8 C10 C3 109.50(10) . . ? C8 C10 H10A 110.8(10) . . ? C3 C10 H10A 110.3(10) . . ? C8 C10 H10B 109.2(10) . . ? C3 C10 H10B 111.1(11) . . ? H10A C10 H10B 105.9(14) . . ? N1 C11 C12 121.77(11) . . ? N1 C11 H11 122.4(10) . . ? C12 C11 H11 115.8(10) . . ? C17 C12 C13 119.21(11) . . ? C17 C12 C11 119.50(11) . . ? C13 C12 C11 121.28(11) . . ? C14 C13 C12 120.89(11) . . ? C14 C13 H13 120.4(10) . . ? C12 C13 H13 118.7(10) . . ? C13 C14 C15 118.58(11) . . ? C13 C14 H14 121.5(11) . . ? C15 C14 H14 119.8(11) . . ? C16 C15 C14 121.89(11) . . ? C16 C15 Cl1 119.01(9) . . ? C14 C15 Cl1 119.09(9) . . ? C15 C16 C17 118.74(11) . . ? C15 C16 H16 119.8(10) . . ? C17 C16 H16 121.4(10) . . ? C16 C17 C12 120.69(11) . . ? C16 C17 H17 119.5(11) . . ? C12 C17 H17 119.7(11) . . ? 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 N1 C1 C7 3.15(15) . . . . ? C11 N1 C1 C2 124.63(11) . . . . ? C11 N1 C1 C6 -118.82(12) . . . . ? N1 C1 C2 C3 175.00(9) . . . . ? C7 C1 C2 C3 -59.12(12) . . . . ? C6 C1 C2 C3 59.26(12) . . . . ? C1 C2 C3 C10 59.66(13) . . . . ? C1 C2 C3 C4 -60.09(13) . . . . ? C10 C3 C4 C5 -59.50(12) . . . . ? C2 C3 C4 C5 60.20(12) . . . . ? C3 C4 C5 C9 59.69(12) . . . . ? C3 C4 C5 C6 -60.34(12) . . . . ? C4 C5 C6 C1 60.02(12) . . . . ? C9 C5 C6 C1 -60.01(13) . . . . ? N1 C1 C6 C5 -174.12(9) . . . . ? C7 C1 C6 C5 59.49(12) . . . . ? C2 C1 C6 C5 -59.02(12) . . . . ? N1 C1 C7 C8 179.14(9) . . . . ? C2 C1 C7 C8 58.92(12) . . . . ? C6 C1 C7 C8 -59.50(12) . . . . ? C1 C7 C8 C10 -59.81(12) . . . . ? C1 C7 C8 C9 60.15(12) . . . . ? C4 C5 C9 C8 -60.26(12) . . . . ? C6 C5 C9 C8 59.71(13) . . . . ? C10 C8 C9 C5 60.58(12) . . . . ? C7 C8 C9 C5 -59.75(13) . . . . ? C9 C8 C10 C3 -60.49(12) . . . . ? C7 C8 C10 C3 59.69(12) . . . . ? C4 C3 C10 C8 60.00(12) . . . . ? C2 C3 C10 C8 -59.49(13) . . . . ? C1 N1 C11 C12 179.41(10) . . . . ? N1 C11 C12 C17 -168.44(11) . . . . ? N1 C11 C12 C13 9.78(17) . . . . ? C17 C12 C13 C14 1.00(17) . . . . ? C11 C12 C13 C14 -177.22(10) . . . . ? C12 C13 C14 C15 -1.16(17) . . . . ? C13 C14 C15 C16 0.75(17) . . . . ? C13 C14 C15 Cl1 -178.44(9) . . . . ? C14 C15 C16 C17 -0.19(18) . . . . ? Cl1 C15 C16 C17 179.00(9) . . . . ? C15 C16 C17 C12 0.03(18) . . . . ? C13 C12 C17 C16 -0.43(18) . . . . ? C11 C12 C17 C16 177.83(10) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.404 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.048 data_ma0402 _database_code_depnum_ccdc_archive 'CCDC 840700' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H20 Br N' _chemical_formula_sum 'C17 H20 Br N' _chemical_formula_weight 318.25 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.680(3) _cell_length_b 6.5071(3) _cell_length_c 16.548(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.150(8) _cell_angle_gamma 90.00 _cell_volume 2832.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 127 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 2.889 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.771 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS, Bruker-Nonius, 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ; \f- and \w-rotations with 2.00 \% and 60 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25383 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 28.69 _reflns_number_total 3650 _reflns_number_gt 2937 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Bruker-Nonius, 2002)' _computing_data_reduction 'EVALCCD (Bruker-Nonius, 2002)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _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^)+(0.0179P)^2^+5.2381P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3650 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0570 _refine_ls_wR_factor_gt 0.0530 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 Br1 Br 0.636126(7) 0.53829(3) 0.541934(12) 0.01856(6) Uani 1 1 d . . . N1 N 0.42120(6) 0.8943(2) 0.62540(10) 0.0141(3) Uani 1 1 d . . . C1 C 0.37463(6) 0.9260(3) 0.64959(11) 0.0122(4) Uani 1 1 d . . . C2 C 0.38264(7) 1.1259(3) 0.70183(13) 0.0150(4) Uani 1 1 d . . . C3 C 0.33420(7) 1.1815(3) 0.72339(12) 0.0154(4) Uani 1 1 d . . . C4 C 0.29049(7) 1.2122(3) 0.64070(12) 0.0165(4) Uani 1 1 d . . . C5 C 0.28159(7) 1.0126(3) 0.58885(12) 0.0153(4) Uani 1 1 d . . . C6 C 0.32995(7) 0.9561(3) 0.56729(11) 0.0141(3) Uani 1 1 d . . . C7 C 0.36104(7) 0.7524(3) 0.70156(12) 0.0127(4) Uani 1 1 d . . . C8 C 0.31247(7) 0.8082(3) 0.72312(12) 0.0152(4) Uani 1 1 d . . . C9 C 0.26841(7) 0.8388(3) 0.64077(13) 0.0168(4) Uani 1 1 d . . . C10 C 0.32101(7) 1.0070(3) 0.77553(12) 0.0169(4) Uani 1 1 d . . . C11 C 0.44573(7) 0.7269(3) 0.64427(11) 0.0133(4) Uani 1 1 d . . . C12 C 0.49206(7) 0.6860(3) 0.62068(11) 0.0133(4) Uani 1 1 d . . . C13 C 0.51578(7) 0.8407(3) 0.58832(11) 0.0137(4) Uani 1 1 d . . . C14 C 0.55824(7) 0.7982(3) 0.56337(12) 0.0143(4) Uani 1 1 d . . . C15 C 0.57704(7) 0.5985(3) 0.57241(11) 0.0137(4) Uani 1 1 d . . . C16 C 0.55438(7) 0.4423(3) 0.60458(11) 0.0149(4) Uani 1 1 d . . . C17 C 0.51179(7) 0.4874(3) 0.62873(11) 0.0148(4) Uani 1 1 d . . . H2A H 0.4109(9) 1.103(4) 0.7534(15) 0.030 Uiso 1 1 d . . . H2B H 0.3910(9) 1.243(4) 0.6680(15) 0.030 Uiso 1 1 d . . . H3 H 0.3402(9) 1.306(4) 0.7557(15) 0.030 Uiso 1 1 d . . . H4A H 0.2588(9) 1.249(4) 0.6532(14) 0.030 Uiso 1 1 d . . . H4B H 0.2973(9) 1.325(4) 0.6044(15) 0.030 Uiso 1 1 d . . . H5 H 0.2542(9) 1.034(4) 0.5378(15) 0.030 Uiso 1 1 d . . . H6A H 0.3228(9) 0.827(4) 0.5340(15) 0.030 Uiso 1 1 d . . . H6B H 0.3372(9) 1.060(4) 0.5345(15) 0.030 Uiso 1 1 d . . . H7A H 0.3554(9) 0.629(4) 0.6690(15) 0.030 Uiso 1 1 d . . . H7B H 0.3916(9) 0.729(4) 0.7568(15) 0.030 Uiso 1 1 d . . . H8 H 0.3033(9) 0.697(4) 0.7582(15) 0.030 Uiso 1 1 d . . . H9A H 0.2381(9) 0.874(4) 0.6551(14) 0.030 Uiso 1 1 d . . . H9B H 0.2627(9) 0.711(4) 0.6053(15) 0.030 Uiso 1 1 d . . . H10A H 0.2893(9) 1.044(4) 0.7880(14) 0.030 Uiso 1 1 d . . . H10B H 0.3503(9) 0.991(4) 0.8325(15) 0.030 Uiso 1 1 d . . . H11 H 0.4362(9) 0.621(4) 0.6753(15) 0.030 Uiso 1 1 d . . . H13 H 0.5023(9) 0.977(4) 0.5828(15) 0.030 Uiso 1 1 d . . . H14 H 0.5739(9) 0.900(4) 0.5388(15) 0.030 Uiso 1 1 d . . . H16 H 0.5685(9) 0.312(4) 0.6100(15) 0.030 Uiso 1 1 d . . . H17 H 0.4956(9) 0.380(4) 0.6504(15) 0.030 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01439(9) 0.02161(10) 0.02174(10) -0.00076(9) 0.00860(7) 0.00450(8) N1 0.0116(7) 0.0165(8) 0.0148(8) -0.0006(6) 0.0050(6) 0.0009(6) C1 0.0114(8) 0.0125(10) 0.0133(9) 0.0009(7) 0.0049(7) 0.0012(7) C2 0.0143(9) 0.0114(9) 0.0190(10) -0.0015(8) 0.0047(8) -0.0003(7) C3 0.0170(9) 0.0110(9) 0.0181(10) -0.0026(8) 0.0055(7) 0.0014(7) C4 0.0164(9) 0.0141(9) 0.0209(10) 0.0026(8) 0.0084(8) 0.0045(8) C5 0.0125(8) 0.0165(10) 0.0149(9) 0.0014(7) 0.0015(7) 0.0025(7) C6 0.0155(8) 0.0143(9) 0.0123(8) 0.0025(8) 0.0041(7) 0.0020(8) C7 0.0123(9) 0.0109(9) 0.0150(9) 0.0012(7) 0.0044(7) 0.0015(7) C8 0.0156(9) 0.0127(9) 0.0198(10) 0.0051(8) 0.0092(8) 0.0033(7) C9 0.0126(9) 0.0150(10) 0.0232(10) 0.0006(8) 0.0060(8) 0.0008(8) C10 0.0155(9) 0.0205(11) 0.0161(9) 0.0017(7) 0.0070(7) 0.0049(8) C11 0.0140(8) 0.0140(9) 0.0116(9) -0.0007(7) 0.0036(7) -0.0007(7) C12 0.0117(8) 0.0161(9) 0.0102(8) -0.0018(7) 0.0005(7) 0.0001(7) C13 0.0132(8) 0.0136(9) 0.0120(9) -0.0006(7) 0.0006(7) 0.0024(7) C14 0.0122(8) 0.0157(9) 0.0131(9) 0.0016(7) 0.0012(7) -0.0001(7) C15 0.0108(8) 0.0189(9) 0.0110(9) -0.0040(7) 0.0029(7) 0.0028(7) C16 0.0151(8) 0.0137(9) 0.0140(9) -0.0011(8) 0.0018(7) 0.0033(8) C17 0.0157(8) 0.0138(10) 0.0138(9) 0.0007(7) 0.0030(7) -0.0006(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 Br1 C15 1.8964(17) . ? N1 C11 1.270(2) . ? N1 C1 1.479(2) . ? C1 C7 1.536(2) . ? C1 C2 1.539(3) . ? C1 C6 1.540(2) . ? C2 C3 1.534(3) . ? C2 H2A 0.97(2) . ? C2 H2B 1.01(2) . ? C3 C4 1.531(3) . ? C3 C10 1.537(3) . ? C3 H3 0.96(2) . ? C4 C5 1.534(3) . ? C4 H4A 0.99(2) . ? C4 H4B 1.00(2) . ? C5 C9 1.532(3) . ? C5 C6 1.534(2) . ? C5 H5 0.95(2) . ? C6 H6A 0.99(2) . ? C6 H6B 0.93(2) . ? C7 C8 1.538(2) . ? C7 H7A 0.96(3) . ? C7 H7B 1.05(2) . ? C8 C9 1.533(3) . ? C8 C10 1.534(3) . ? C8 H8 1.01(2) . ? C9 H9A 0.97(2) . ? C9 H9B 1.00(2) . ? C10 H10A 0.99(2) . ? C10 H10B 1.04(2) . ? C11 C12 1.476(2) . ? C11 H11 0.95(2) . ? C12 C17 1.393(3) . ? C12 C13 1.397(3) . ? C13 C14 1.389(3) . ? C13 H13 0.95(2) . ? C14 C15 1.391(3) . ? C14 H14 0.95(2) . ? C15 C16 1.385(3) . ? C16 C17 1.389(3) . ? C16 H16 0.93(3) . ? C17 H17 0.96(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 C11 N1 C1 119.84(16) . . ? N1 C1 C7 115.80(14) . . ? N1 C1 C2 106.54(14) . . ? C7 C1 C2 108.94(15) . . ? N1 C1 C6 107.81(14) . . ? C7 C1 C6 108.62(15) . . ? C2 C1 C6 108.96(15) . . ? C3 C2 C1 110.26(15) . . ? C3 C2 H2A 110.8(14) . . ? C1 C2 H2A 107.2(14) . . ? C3 C2 H2B 108.6(13) . . ? C1 C2 H2B 110.0(13) . . ? H2A C2 H2B 110.0(19) . . ? C4 C3 C2 109.12(16) . . ? C4 C3 C10 109.78(16) . . ? C2 C3 C10 109.53(15) . . ? C4 C3 H3 109.8(14) . . ? C2 C3 H3 108.6(14) . . ? C10 C3 H3 110.0(14) . . ? C3 C4 C5 109.49(15) . . ? C3 C4 H4A 110.4(13) . . ? C5 C4 H4A 108.8(14) . . ? C3 C4 H4B 112.8(13) . . ? C5 C4 H4B 108.2(13) . . ? H4A C4 H4B 107.0(19) . . ? C9 C5 C6 109.33(15) . . ? C9 C5 C4 109.66(15) . . ? C6 C5 C4 109.49(16) . . ? C9 C5 H5 109.9(14) . . ? C6 C5 H5 109.8(14) . . ? C4 C5 H5 108.7(14) . . ? C5 C6 C1 110.07(14) . . ? C5 C6 H6A 107.2(13) . . ? C1 C6 H6A 110.5(13) . . ? C5 C6 H6B 108.9(14) . . ? C1 C6 H6B 110.4(15) . . ? H6A C6 H6B 109.6(19) . . ? C1 C7 C8 109.92(15) . . ? C1 C7 H7A 109.3(14) . . ? C8 C7 H7A 109.1(14) . . ? C1 C7 H7B 108.9(13) . . ? C8 C7 H7B 111.0(13) . . ? H7A C7 H7B 108.5(19) . . ? C9 C8 C10 109.44(15) . . ? C9 C8 C7 109.60(15) . . ? C10 C8 C7 109.77(15) . . ? C9 C8 H8 109.3(13) . . ? C10 C8 H8 107.5(13) . . ? C7 C8 H8 111.1(13) . . ? C5 C9 C8 109.39(15) . . ? C5 C9 H9A 109.8(14) . . ? C8 C9 H9A 108.9(14) . . ? C5 C9 H9B 107.8(13) . . ? C8 C9 H9B 110.5(13) . . ? H9A C9 H9B 110.3(19) . . ? C8 C10 C3 109.09(15) . . ? C8 C10 H10A 109.3(14) . . ? C3 C10 H10A 108.6(14) . . ? C8 C10 H10B 111.5(13) . . ? C3 C10 H10B 109.2(13) . . ? H10A C10 H10B 109.1(18) . . ? N1 C11 C12 122.12(17) . . ? N1 C11 H11 122.7(14) . . ? C12 C11 H11 115.2(14) . . ? C17 C12 C13 119.23(17) . . ? C17 C12 C11 119.27(17) . . ? C13 C12 C11 121.48(17) . . ? C14 C13 C12 120.83(17) . . ? C14 C13 H13 119.9(14) . . ? C12 C13 H13 119.2(14) . . ? C13 C14 C15 118.50(17) . . ? C13 C14 H14 122.0(14) . . ? C15 C14 H14 119.4(14) . . ? C16 C15 C14 121.87(17) . . ? C16 C15 Br1 118.82(14) . . ? C14 C15 Br1 119.30(14) . . ? C15 C16 C17 118.84(18) . . ? C15 C16 H16 118.7(14) . . ? C17 C16 H16 122.5(14) . . ? C16 C17 C12 120.73(18) . . ? C16 C17 H17 119.4(14) . . ? C12 C17 H17 119.8(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C1 C7 3.3(2) . . . . ? C11 N1 C1 C2 124.63(18) . . . . ? C11 N1 C1 C6 -118.54(18) . . . . ? N1 C1 C2 C3 175.15(15) . . . . ? C7 C1 C2 C3 -59.3(2) . . . . ? C6 C1 C2 C3 59.08(19) . . . . ? C1 C2 C3 C4 -60.2(2) . . . . ? C1 C2 C3 C10 60.0(2) . . . . ? C2 C3 C4 C5 60.5(2) . . . . ? C10 C3 C4 C5 -59.57(19) . . . . ? C3 C4 C5 C9 59.53(19) . . . . ? C3 C4 C5 C6 -60.42(19) . . . . ? C9 C5 C6 C1 -60.4(2) . . . . ? C4 C5 C6 C1 59.7(2) . . . . ? N1 C1 C6 C5 -173.95(15) . . . . ? C7 C1 C6 C5 59.9(2) . . . . ? C2 C1 C6 C5 -58.7(2) . . . . ? N1 C1 C7 C8 179.11(15) . . . . ? C2 C1 C7 C8 59.09(19) . . . . ? C6 C1 C7 C8 -59.47(19) . . . . ? C1 C7 C8 C9 60.1(2) . . . . ? C1 C7 C8 C10 -60.2(2) . . . . ? C6 C5 C9 C8 60.0(2) . . . . ? C4 C5 C9 C8 -60.02(19) . . . . ? C10 C8 C9 C5 60.52(19) . . . . ? C7 C8 C9 C5 -59.9(2) . . . . ? C9 C8 C10 C3 -60.31(19) . . . . ? C7 C8 C10 C3 60.02(19) . . . . ? C4 C3 C10 C8 59.96(19) . . . . ? C2 C3 C10 C8 -59.8(2) . . . . ? C1 N1 C11 C12 179.16(16) . . . . ? N1 C11 C12 C17 -168.05(18) . . . . ? N1 C11 C12 C13 10.2(3) . . . . ? C17 C12 C13 C14 0.7(3) . . . . ? C11 C12 C13 C14 -177.54(17) . . . . ? C12 C13 C14 C15 -0.8(3) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C13 C14 C15 Br1 -178.17(13) . . . . ? C14 C15 C16 C17 -0.3(3) . . . . ? Br1 C15 C16 C17 178.54(13) . . . . ? C15 C16 C17 C12 0.1(3) . . . . ? C13 C12 C17 C16 -0.3(3) . . . . ? C11 C12 C17 C16 177.96(17) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.69 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.377 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.074 data_ma0404 _database_code_depnum_ccdc_archive 'CCDC 840701' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 N O' _chemical_formula_sum 'C18 H23 N O' _chemical_formula_weight 269.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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) _symmetry_space_group_name_Hall P2yb _chemical_absolute_configuration unk loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.7598(4) _cell_length_b 6.7421(2) _cell_length_c 15.7289(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.646(4) _cell_angle_gamma 90.00 _cell_volume 715.40(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 77 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.944 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS, Bruker-Nonius, 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ; \f- and \w-rotations with 2.00 \% and 120 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18633 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0156 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 27.87 _reflns_number_total 1838 _reflns_number_gt 1715 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Bruker-Nonius, 2002)' _computing_data_reduction 'EVALCCD (Bruker-Nonius, 2002)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _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^)+(0.0589P)^2^+0.1430P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1838 _refine_ls_number_parameters 250 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.52537(17) 0.0318(3) 0.82162(7) 0.0175(3) Uani 1 1 d . . . N1 N 0.9505(2) 0.0243(3) 1.20432(9) 0.0158(3) Uani 1 1 d . . . C1 C 1.1067(2) 0.0341(3) 1.27478(10) 0.0135(3) Uani 1 1 d . . . C2 C 1.0713(4) 0.2224(3) 1.32703(15) 0.0182(5) Uani 1 1 d . . . C3 C 1.2188(4) 0.2298(3) 1.40570(15) 0.0183(5) Uani 1 1 d . . . C4 C 1.1901(3) 0.0469(4) 1.46149(11) 0.0194(4) Uani 1 1 d . . . C5 C 1.2276(3) -0.1413(3) 1.41018(14) 0.0179(5) Uani 1 1 d . . . C6 C 1.0811(3) -0.1485(3) 1.33147(15) 0.0168(4) Uani 1 1 d . . . C7 C 1.3215(2) 0.0382(3) 1.24716(10) 0.0149(3) Uani 1 1 d . . . C8 C 1.4683(2) 0.0451(4) 1.32570(10) 0.0165(4) Uani 1 1 d . . . C9 C 1.4404(4) -0.1379(3) 1.38106(15) 0.0195(5) Uani 1 1 d . . . C10 C 1.4317(4) 0.2330(3) 1.37692(15) 0.0190(5) Uani 1 1 d . . . C11 C 0.9990(2) 0.0551(3) 1.12915(11) 0.0141(4) Uani 1 1 d . . . C12 C 0.8608(2) 0.0479(3) 1.05270(10) 0.0139(3) Uani 1 1 d . . . C13 C 0.6617(3) -0.0055(3) 1.05225(11) 0.0152(4) Uani 1 1 d . . . C14 C 0.5428(3) -0.0146(3) 0.97684(11) 0.0153(4) Uani 1 1 d . . . C15 C 0.6243(2) 0.0318(3) 0.89992(10) 0.0138(3) Uani 1 1 d . . . C16 C 0.8241(3) 0.0834(3) 0.89950(12) 0.0158(4) Uani 1 1 d . . . C17 C 0.9393(3) 0.0912(3) 0.97465(12) 0.0158(4) Uani 1 1 d . . . C18 C 0.3168(3) -0.0009(4) 0.81688(13) 0.0223(5) Uani 1 1 d . . . H2A H 0.934(6) 0.219(5) 1.345(2) 0.040 Uiso 1 1 d . . . H2B H 1.091(5) 0.344(5) 1.289(2) 0.040 Uiso 1 1 d . . . H3 H 1.197(5) 0.354(5) 1.440(2) 0.040 Uiso 1 1 d . . . H4A H 1.280(4) 0.053(6) 1.5124(16) 0.040 Uiso 1 1 d . . . H4B H 1.048(4) 0.044(6) 1.4798(15) 0.040 Uiso 1 1 d . . . H5 H 1.214(5) -0.262(5) 1.445(2) 0.040 Uiso 1 1 d . . . H6A H 0.945(6) -0.157(5) 1.349(2) 0.040 Uiso 1 1 d . . . H6B H 1.097(5) -0.273(5) 1.297(2) 0.040 Uiso 1 1 d . . . H7A H 1.343(5) -0.083(5) 1.212(3) 0.040 Uiso 1 1 d . . . H7B H 1.351(5) 0.159(6) 1.212(2) 0.040 Uiso 1 1 d . . . H8 H 1.602(4) 0.052(6) 1.3047(16) 0.040 Uiso 1 1 d . . . H9A H 1.463(6) -0.262(5) 1.346(2) 0.040 Uiso 1 1 d . . . H9B H 1.537(5) -0.138(5) 1.430(2) 0.040 Uiso 1 1 d . . . H10A H 1.526(5) 0.238(6) 1.428(2) 0.040 Uiso 1 1 d . . . H10B H 1.452(5) 0.352(5) 1.342(2) 0.040 Uiso 1 1 d . . . H11 H 1.133(4) 0.089(5) 1.1143(17) 0.040 Uiso 1 1 d . . . H13 H 0.601(4) -0.037(5) 1.1042(18) 0.040 Uiso 1 1 d . . . H14 H 0.407(4) -0.051(5) 0.9783(18) 0.040 Uiso 1 1 d . . . H16 H 0.876(4) 0.111(5) 0.8462(19) 0.040 Uiso 1 1 d . . . H17 H 1.081(4) 0.127(5) 0.9748(18) 0.040 Uiso 1 1 d . . . H18A H 0.281(5) -0.132(5) 0.840(2) 0.040 Uiso 1 1 d . . . H18B H 0.279(4) 0.002(5) 0.7577(17) 0.040 Uiso 1 1 d . . . H18C H 0.251(4) 0.105(5) 0.8516(18) 0.040 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0139(6) 0.0247(7) 0.0136(5) -0.0010(7) -0.0023(4) -0.0016(6) N1 0.0142(6) 0.0172(8) 0.0158(6) -0.0014(7) -0.0011(5) 0.0000(7) C1 0.0125(7) 0.0154(8) 0.0124(7) 0.0002(8) -0.0008(6) -0.0005(8) C2 0.0181(11) 0.0189(11) 0.0172(11) -0.0028(8) -0.0027(9) 0.0038(8) C3 0.0222(12) 0.0162(10) 0.0161(11) -0.0043(8) -0.0023(9) 0.0028(8) C4 0.0183(8) 0.0266(10) 0.0133(7) -0.0007(9) 0.0008(6) -0.0016(10) C5 0.0227(12) 0.0171(10) 0.0138(10) 0.0053(8) -0.0006(8) -0.0034(8) C6 0.0180(11) 0.0171(10) 0.0153(10) -0.0002(8) 0.0004(8) -0.0060(8) C7 0.0131(7) 0.0192(9) 0.0124(7) -0.0003(9) -0.0006(6) 0.0001(9) C8 0.0116(7) 0.0242(9) 0.0133(7) -0.0005(9) -0.0007(6) -0.0005(9) C9 0.0207(11) 0.0201(11) 0.0171(11) 0.0000(8) -0.0033(9) 0.0059(8) C10 0.0207(12) 0.0195(11) 0.0162(11) -0.0007(8) -0.0035(9) -0.0062(8) C11 0.0122(7) 0.0136(9) 0.0163(7) 0.0015(8) -0.0011(6) 0.0015(8) C12 0.0155(7) 0.0111(8) 0.0148(7) -0.0010(8) -0.0007(6) 0.0028(8) C13 0.0169(8) 0.0159(10) 0.0129(8) 0.0016(7) 0.0023(6) 0.0009(7) C14 0.0122(8) 0.0167(10) 0.0171(8) -0.0006(7) 0.0012(6) -0.0012(7) C15 0.0170(8) 0.0108(8) 0.0131(7) 0.0011(8) -0.0031(6) 0.0011(8) C16 0.0158(8) 0.0178(11) 0.0139(8) 0.0029(7) 0.0013(6) 0.0003(7) C17 0.0127(8) 0.0159(10) 0.0187(9) 0.0022(7) -0.0006(6) -0.0010(7) C18 0.0152(8) 0.0332(14) 0.0177(9) 0.0010(9) -0.0047(7) -0.0056(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.3636(18) . ? O1 C18 1.424(2) . ? N1 C11 1.264(2) . ? N1 C1 1.483(2) . ? C1 C6 1.536(3) . ? C1 C7 1.542(2) . ? C1 C2 1.540(3) . ? C2 C3 1.540(3) . ? C2 H2A 0.99(4) . ? C2 H2B 1.02(4) . ? C3 C10 1.536(3) . ? C3 C4 1.533(3) . ? C3 H3 1.01(4) . ? C4 C5 1.533(3) . ? C4 H4A 0.98(3) . ? C4 H4B 1.02(3) . ? C5 C6 1.536(3) . ? C5 C9 1.537(3) . ? C5 H5 0.99(4) . ? C6 H6A 0.98(4) . ? C6 H6B 1.00(4) . ? C7 C8 1.535(2) . ? C7 H7A 1.00(4) . ? C7 H7B 1.02(4) . ? C8 C9 1.529(3) . ? C8 C10 1.530(3) . ? C8 H8 0.98(3) . ? C9 H9A 1.02(4) . ? C9 H9B 0.97(4) . ? C10 H10A 0.99(4) . ? C10 H10B 0.99(4) . ? C11 C12 1.476(2) . ? C11 H11 0.98(3) . ? C12 C13 1.393(2) . ? C12 C17 1.399(2) . ? C13 C14 1.391(2) . ? C13 H13 0.96(3) . ? C14 C15 1.397(2) . ? C14 H14 0.95(3) . ? C15 C16 1.395(2) . ? C16 C17 1.374(3) . ? C16 H16 0.95(3) . ? C17 H17 0.99(3) . ? C18 H18A 0.99(4) . ? C18 H18B 0.95(3) . ? C18 H18C 1.02(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 C15 O1 C18 118.32(13) . . ? C11 N1 C1 118.51(14) . . ? N1 C1 C6 107.28(16) . . ? N1 C1 C7 115.38(12) . . ? C6 C1 C7 108.73(17) . . ? N1 C1 C2 107.95(16) . . ? C6 C1 C2 108.90(13) . . ? C7 C1 C2 108.45(17) . . ? C3 C2 C1 109.94(17) . . ? C3 C2 H2A 110(2) . . ? C1 C2 H2A 108(2) . . ? C3 C2 H2B 110(2) . . ? C1 C2 H2B 109(2) . . ? H2A C2 H2B 110(3) . . ? C10 C3 C4 109.56(17) . . ? C10 C3 C2 109.5(2) . . ? C4 C3 C2 109.57(18) . . ? C10 C3 H3 108(2) . . ? C4 C3 H3 110(2) . . ? C2 C3 H3 110(2) . . ? C5 C4 C3 109.47(13) . . ? C5 C4 H4A 111(2) . . ? C3 C4 H4A 110(2) . . ? C5 C4 H4B 109(2) . . ? C3 C4 H4B 109(2) . . ? H4A C4 H4B 109(2) . . ? C4 C5 C6 109.29(18) . . ? C4 C5 C9 109.51(18) . . ? C6 C5 C9 109.14(19) . . ? C4 C5 H5 111(2) . . ? C6 C5 H5 110(2) . . ? C9 C5 H5 107(2) . . ? C5 C6 C1 110.60(16) . . ? C5 C6 H6A 110(2) . . ? C1 C6 H6A 111(2) . . ? C5 C6 H6B 112(2) . . ? C1 C6 H6B 110(2) . . ? H6A C6 H6B 104(3) . . ? C8 C7 C1 110.22(13) . . ? C8 C7 H7A 111(2) . . ? C1 C7 H7A 108(2) . . ? C8 C7 H7B 106(2) . . ? C1 C7 H7B 113(2) . . ? H7A C7 H7B 108(2) . . ? C9 C8 C10 109.80(14) . . ? C9 C8 C7 109.70(18) . . ? C10 C8 C7 109.31(18) . . ? C9 C8 H8 112(2) . . ? C10 C8 H8 109(2) . . ? C7 C8 H8 106.9(15) . . ? C8 C9 C5 109.46(17) . . ? C8 C9 H9A 109(2) . . ? C5 C9 H9A 109(2) . . ? C8 C9 H9B 110(2) . . ? C5 C9 H9B 111(2) . . ? H9A C9 H9B 108(3) . . ? C8 C10 C3 109.24(17) . . ? C8 C10 H10A 110(2) . . ? C3 C10 H10A 109(2) . . ? C8 C10 H10B 110(2) . . ? C3 C10 H10B 110(2) . . ? H10A C10 H10B 109(3) . . ? N1 C11 C12 124.65(15) . . ? N1 C11 H11 124.1(16) . . ? C12 C11 H11 111.2(16) . . ? C13 C12 C17 118.01(15) . . ? C13 C12 C11 125.03(15) . . ? C17 C12 C11 116.92(15) . . ? C14 C13 C12 121.43(16) . . ? C14 C13 H13 117.6(18) . . ? C12 C13 H13 121.0(18) . . ? C13 C14 C15 119.35(16) . . ? C13 C14 H14 119.8(17) . . ? C15 C14 H14 120.9(17) . . ? O1 C15 C16 114.53(14) . . ? O1 C15 C14 125.76(15) . . ? C16 C15 C14 119.71(15) . . ? C17 C16 C15 120.06(16) . . ? C17 C16 H16 122.1(18) . . ? C15 C16 H16 117.9(18) . . ? C16 C17 C12 121.42(16) . . ? C16 C17 H17 120.5(16) . . ? C12 C17 H17 118.0(16) . . ? O1 C18 H18A 112.4(18) . . ? O1 C18 H18B 104.4(16) . . ? H18A C18 H18B 109(3) . . ? O1 C18 H18C 109.4(17) . . ? H18A C18 H18C 107(2) . . ? H18B C18 H18C 114(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 N1 C1 C6 -133.6(2) . . . . ? C11 N1 C1 C7 -12.3(3) . . . . ? C11 N1 C1 C2 109.2(2) . . . . ? N1 C1 C2 C3 175.03(17) . . . . ? C6 C1 C2 C3 58.9(2) . . . . ? C7 C1 C2 C3 -59.3(2) . . . . ? C1 C2 C3 C10 60.2(2) . . . . ? C1 C2 C3 C4 -60.0(2) . . . . ? C10 C3 C4 C5 -60.0(2) . . . . ? C2 C3 C4 C5 60.2(2) . . . . ? C3 C4 C5 C6 -59.8(2) . . . . ? C3 C4 C5 C9 59.7(2) . . . . ? C4 C5 C6 C1 59.7(2) . . . . ? C9 C5 C6 C1 -60.0(2) . . . . ? N1 C1 C6 C5 -175.61(16) . . . . ? C7 C1 C6 C5 59.0(2) . . . . ? C2 C1 C6 C5 -59.0(2) . . . . ? N1 C1 C7 C8 -179.13(19) . . . . ? C6 C1 C7 C8 -58.6(2) . . . . ? C2 C1 C7 C8 59.7(2) . . . . ? C1 C7 C8 C9 59.8(2) . . . . ? C1 C7 C8 C10 -60.6(2) . . . . ? C10 C8 C9 C5 60.0(2) . . . . ? C7 C8 C9 C5 -60.1(2) . . . . ? C4 C5 C9 C8 -59.7(2) . . . . ? C6 C5 C9 C8 59.9(2) . . . . ? C9 C8 C10 C3 -60.1(2) . . . . ? C7 C8 C10 C3 60.3(2) . . . . ? C4 C3 C10 C8 60.0(2) . . . . ? C2 C3 C10 C8 -60.2(2) . . . . ? C1 N1 C11 C12 179.2(2) . . . . ? N1 C11 C12 C13 -4.1(3) . . . . ? N1 C11 C12 C17 178.3(2) . . . . ? C17 C12 C13 C14 -0.4(3) . . . . ? C11 C12 C13 C14 -178.0(2) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C18 O1 C15 C16 -174.2(2) . . . . ? C18 O1 C15 C14 5.9(3) . . . . ? C13 C14 C15 O1 -179.10(19) . . . . ? C13 C14 C15 C16 1.0(3) . . . . ? O1 C15 C16 C17 179.19(18) . . . . ? C14 C15 C16 C17 -0.9(3) . . . . ? C15 C16 C17 C12 0.1(3) . . . . ? C13 C12 C17 C16 0.6(3) . . . . ? C11 C12 C17 C16 178.26(18) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.286 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.043 data_ma0406 _database_code_depnum_ccdc_archive 'CCDC 840702' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H28 Cl N' _chemical_formula_sum 'C22 H28 Cl N' _chemical_formula_weight 341.90 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)/c _symmetry_space_group_name_Hall -P2ybc 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 9.2529(9) _cell_length_b 15.6034(8) _cell_length_c 12.4998(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.055(9) _cell_angle_gamma 90.00 _cell_volume 1804.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 132 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS, Bruker-Nonius, 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ; \w-rotations with 2.00 \% and 240 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34333 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0231 _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 -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3687 _reflns_number_gt 3028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Bruker-Nonius, 2002)' _computing_data_reduction 'EVALCCD (Bruker-Nonius, 2002)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _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^)+(0.0254P)^2^+1.3218P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom except N bound H difmap/noref' _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3687 _refine_ls_number_parameters 254 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _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 0.86696(5) 0.07942(4) 0.41337(4) 0.03359(14) Uani 1 1 d . . . N1 N 0.53504(15) 0.13349(9) -0.06269(11) 0.0203(3) Uani 1 1 d . . . H1 H 0.5156 0.1185 -0.1343 0.024 Uiso 1 1 d . . . C1 C 0.45370(18) 0.21367(10) -0.04539(13) 0.0183(3) Uani 1 1 d . . . C2 C 0.5025(2) 0.28796(11) -0.11717(14) 0.0246(4) Uani 1 1 d . . . H2A H 0.6044 0.3026 -0.0999 0.029 Uiso 1 1 calc R . . H2B H 0.4964 0.2701 -0.1931 0.029 Uiso 1 1 calc R . . C3 C 0.4066(2) 0.36703(12) -0.10025(15) 0.0289(4) Uani 1 1 d . . . H3A H 0.4398 0.4148 -0.1472 0.035 Uiso 1 1 calc R . . C4 C 0.2496(2) 0.34464(12) -0.12898(15) 0.0292(4) Uani 1 1 d . . . H4A H 0.2421 0.3267 -0.2048 0.035 Uiso 1 1 calc R . . H4B H 0.1874 0.3956 -0.1193 0.035 Uiso 1 1 calc R . . C5 C 0.1988(2) 0.27157(12) -0.05637(15) 0.0263(4) Uani 1 1 d . . . H5A H 0.0962 0.2568 -0.0747 0.032 Uiso 1 1 calc R . . C6 C 0.29471(19) 0.19289(11) -0.07224(15) 0.0239(4) Uani 1 1 d . . . H6A H 0.2860 0.1733 -0.1474 0.029 Uiso 1 1 calc R . . H6B H 0.2616 0.1458 -0.0256 0.029 Uiso 1 1 calc R . . C7 C 0.46366(19) 0.24246(11) 0.07171(13) 0.0225(4) Uani 1 1 d . . . H7A H 0.5652 0.2564 0.0910 0.027 Uiso 1 1 calc R . . H7B H 0.4316 0.1954 0.1188 0.027 Uiso 1 1 calc R . . C8 C 0.3680(2) 0.32174(12) 0.08833(14) 0.0275(4) Uani 1 1 d . . . H8A H 0.3757 0.3402 0.1648 0.033 Uiso 1 1 calc R . . C9 C 0.2105(2) 0.30044(13) 0.06072(15) 0.0293(4) Uani 1 1 d . . . H9A H 0.1492 0.3516 0.0717 0.035 Uiso 1 1 calc R . . H9B H 0.1761 0.2542 0.1081 0.035 Uiso 1 1 calc R . . C10 C 0.4191(2) 0.39468(12) 0.01663(16) 0.0319(4) Uani 1 1 d . . . H10A H 0.3593 0.4463 0.0283 0.038 Uiso 1 1 calc R . . H10B H 0.5209 0.4091 0.0347 0.038 Uiso 1 1 calc R . . C11 C 0.69307(18) 0.13556(12) -0.04945(13) 0.0222(4) Uani 1 1 d . A . H11A H 0.7291 0.1929 -0.0729 0.027 Uiso 1 1 calc R . . C12 C 0.73740(18) 0.12161(11) 0.06686(13) 0.0196(3) Uani 1 1 d . . . C13 C 0.84410(18) 0.17189(12) 0.11562(14) 0.0234(4) Uani 1 1 d . . . H13A H 0.8898 0.2156 0.0755 0.028 Uiso 1 1 calc R . . C14 C 0.88485(19) 0.15924(12) 0.22189(14) 0.0248(4) Uani 1 1 d . . . H14A H 0.9575 0.1940 0.2546 0.030 Uiso 1 1 calc R . . C15 C 0.81822(19) 0.09541(12) 0.27922(14) 0.0234(4) Uani 1 1 d . . . C16 C 0.71252(18) 0.04404(11) 0.23257(14) 0.0240(4) Uani 1 1 d . . . H16A H 0.6676 0.0002 0.2729 0.029 Uiso 1 1 calc R . . C17 C 0.67312(18) 0.05730(11) 0.12674(14) 0.0220(4) Uani 1 1 d . . . H17A H 0.6010 0.0220 0.0943 0.026 Uiso 1 1 calc R . . C18 C 0.7583(2) 0.06576(15) -0.12164(15) 0.0335(5) Uani 1 1 d D . . H18A H 0.7197 0.0102 -0.0943 0.040 Uiso 0.523(13) 1 calc PR A 1 H18B H 0.7263 0.0059 -0.1061 0.040 Uiso 0.477(13) 1 calc PR A 2 C19 C 0.7154(10) 0.0681(6) -0.2408(4) 0.0290(18) Uani 0.523(13) 1 d PD A 1 H19A H 0.6242 0.0524 -0.2710 0.035 Uiso 0.523(13) 1 calc PR A 1 C20 C 0.8266(9) 0.0957(6) -0.2930(7) 0.0274(19) Uani 0.523(13) 1 d PD A 1 H20A H 0.8209 0.1109 -0.3666 0.033 Uiso 0.523(13) 1 calc PR A 1 C21 C 0.9656(13) 0.1015(10) -0.2277(9) 0.031(3) Uani 0.523(13) 1 d PD A 1 H21A H 0.9924 0.1618 -0.2126 0.038 Uiso 0.523(13) 1 calc PR A 1 H21B H 1.0464 0.0726 -0.2639 0.038 Uiso 0.523(13) 1 calc PR A 1 C22 C 0.9229(5) 0.0538(5) -0.1254(9) 0.0277(18) Uani 0.523(13) 1 d PD A 1 H22A H 0.9487 -0.0077 -0.1297 0.033 Uiso 0.523(13) 1 calc PR A 1 H22B H 0.9711 0.0792 -0.0615 0.033 Uiso 0.523(13) 1 calc PR A 1 C19' C 0.7296(10) 0.0968(6) -0.2396(5) 0.0241(17) Uani 0.477(13) 1 d PD A 2 H19B H 0.6516 0.0622 -0.2735 0.029 Uiso 0.477(13) 1 calc PR A 2 H19C H 0.6994 0.1576 -0.2401 0.029 Uiso 0.477(13) 1 calc PR A 2 C20' C 0.8715(9) 0.0859(6) -0.3014(9) 0.0234(16) Uani 0.477(13) 1 d PD A 2 H20B H 0.8735 0.0310 -0.3412 0.028 Uiso 0.477(13) 1 calc PR A 2 H20C H 0.8873 0.1340 -0.3516 0.028 Uiso 0.477(13) 1 calc PR A 2 C21' C 0.9784(14) 0.0867(10) -0.2112(10) 0.028(2) Uani 0.477(13) 1 d PD A 2 H21C H 1.0794 0.0915 -0.2223 0.033 Uiso 0.477(13) 1 calc PR A 2 C22' C 0.9243(7) 0.0805(7) -0.1159(9) 0.0248(18) Uani 0.477(13) 1 d PD A 2 H22C H 0.9794 0.0845 -0.0512 0.030 Uiso 0.477(13) 1 calc PR A 2 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 0.0302(2) 0.0517(3) 0.0187(2) 0.0035(2) -0.00286(17) -0.0036(2) N1 0.0203(7) 0.0212(7) 0.0193(7) -0.0011(6) -0.0029(6) -0.0010(6) C1 0.0198(8) 0.0185(8) 0.0166(8) -0.0004(6) -0.0001(6) 0.0004(6) C2 0.0261(9) 0.0265(9) 0.0213(9) 0.0043(7) 0.0050(7) 0.0011(7) C3 0.0350(10) 0.0217(9) 0.0301(10) 0.0091(8) 0.0074(8) 0.0019(8) C4 0.0338(10) 0.0307(10) 0.0233(9) 0.0044(8) 0.0012(8) 0.0116(8) C5 0.0220(9) 0.0291(10) 0.0278(10) 0.0009(8) -0.0001(7) 0.0008(8) C6 0.0230(9) 0.0248(9) 0.0238(9) -0.0011(7) -0.0028(7) -0.0018(7) C7 0.0260(9) 0.0245(9) 0.0172(8) -0.0009(7) -0.0001(7) 0.0011(7) C8 0.0338(10) 0.0296(10) 0.0192(9) -0.0061(7) 0.0020(7) 0.0040(8) C9 0.0300(10) 0.0331(10) 0.0253(10) 0.0033(8) 0.0082(8) 0.0063(8) C10 0.0359(11) 0.0203(9) 0.0394(11) -0.0050(8) 0.0019(9) 0.0021(8) C11 0.0188(8) 0.0270(9) 0.0206(9) 0.0029(7) -0.0016(7) -0.0013(7) C12 0.0169(8) 0.0209(8) 0.0211(8) -0.0002(7) 0.0006(6) 0.0021(7) C13 0.0208(8) 0.0238(9) 0.0256(9) 0.0026(7) 0.0007(7) -0.0027(7) C14 0.0212(9) 0.0275(10) 0.0255(9) -0.0028(7) -0.0033(7) -0.0037(7) C15 0.0212(9) 0.0314(10) 0.0176(8) -0.0004(7) -0.0008(7) 0.0045(7) C16 0.0225(9) 0.0240(9) 0.0257(9) 0.0050(7) 0.0031(7) -0.0014(7) C17 0.0189(8) 0.0214(9) 0.0257(9) -0.0008(7) -0.0027(7) -0.0018(7) C18 0.0262(10) 0.0516(13) 0.0226(9) -0.0036(9) 0.0004(7) 0.0088(9) C19 0.032(3) 0.027(4) 0.028(3) -0.019(2) -0.0067(19) 0.002(3) C20 0.038(5) 0.028(3) 0.016(3) -0.0032(18) 0.000(3) 0.016(3) C21 0.037(4) 0.033(5) 0.024(3) 0.009(3) 0.010(3) 0.003(3) C22 0.033(3) 0.026(4) 0.024(3) -0.008(3) 0.0025(19) 0.014(2) C19' 0.025(3) 0.029(4) 0.019(3) -0.014(2) -0.002(2) 0.001(3) C20' 0.022(4) 0.020(3) 0.028(3) -0.005(2) 0.007(3) 0.006(3) C21' 0.028(3) 0.024(5) 0.031(5) -0.004(4) -0.002(3) -0.002(3) C22' 0.024(3) 0.028(5) 0.022(3) -0.010(3) -0.0027(18) 0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C15 1.7463(17) . ? N1 C11 1.469(2) . ? N1 C1 1.478(2) . ? N1 H1 0.9398 . ? C1 C7 1.532(2) . ? C1 C6 1.537(2) . ? C1 C2 1.539(2) . ? C2 C3 1.537(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C10 1.526(3) . ? C3 C4 1.530(3) . ? C3 H3A 1.0000 . ? C4 C5 1.536(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.530(3) . ? C5 C9 1.533(3) . ? C5 H5A 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.537(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.528(3) . ? C8 C10 1.529(3) . ? C8 H8A 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.519(2) . ? C11 C18 1.544(3) . ? C11 H11A 1.0000 . ? C12 C17 1.392(2) . ? C12 C13 1.393(2) . ? C13 C14 1.388(2) . ? C13 H13A 0.9500 . ? C14 C15 1.379(3) . ? C14 H14A 0.9500 . ? C15 C16 1.385(2) . ? C16 C17 1.381(2) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 C19 1.535(4) . ? C18 C22 1.537(4) . ? C18 C22' 1.554(7) . ? C18 C19' 1.569(6) . ? C18 H18A 1.0000 . ? C18 H18B 1.0000 . ? C19 C20 1.301(8) . ? C19 H19A 0.9500 . ? C20 C21 1.514(7) . ? C20 H20A 0.9500 . ? C21 C22 1.537(8) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C19' C20' 1.546(11) . ? C19' H19B 0.9900 . ? C19' H19C 0.9900 . ? C20' C21' 1.487(9) . ? C20' H20B 0.9900 . ? C20' H20C 0.9900 . ? C21' C22' 1.305(12) . ? C21' H21C 0.9500 . ? C22' H22C 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N1 C1 118.26(13) . . ? C11 N1 H1 106.6 . . ? C1 N1 H1 105.1 . . ? N1 C1 C7 111.48(13) . . ? N1 C1 C6 106.10(13) . . ? C7 C1 C6 108.11(14) . . ? N1 C1 C2 113.38(13) . . ? C7 C1 C2 108.85(14) . . ? C6 C1 C2 108.74(14) . . ? C3 C2 C1 110.38(14) . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C10 C3 C4 110.15(16) . . ? C10 C3 C2 108.96(15) . . ? C4 C3 C2 109.42(16) . . ? C10 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C3 C4 C5 109.28(15) . . ? C3 C4 H4A 109.8 . . ? C5 C4 H4A 109.8 . . ? C3 C4 H4B 109.8 . . ? C5 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? C6 C5 C9 109.20(15) . . ? C6 C5 C4 109.54(15) . . ? C9 C5 C4 109.21(16) . . ? C6 C5 H5A 109.6 . . ? C9 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? C5 C6 C1 110.94(14) . . ? C5 C6 H6A 109.5 . . ? C1 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? C1 C7 C8 109.90(14) . . ? C1 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? C1 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C9 C8 C10 109.50(16) . . ? C9 C8 C7 110.10(15) . . ? C10 C8 C7 109.53(15) . . ? C9 C8 H8A 109.2 . . ? C10 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? C8 C9 C5 109.23(15) . . ? C8 C9 H9A 109.8 . . ? C5 C9 H9A 109.8 . . ? C8 C9 H9B 109.8 . . ? C5 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? C3 C10 C8 109.38(15) . . ? C3 C10 H10A 109.8 . . ? C8 C10 H10A 109.8 . . ? C3 C10 H10B 109.8 . . ? C8 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? N1 C11 C12 110.81(14) . . ? N1 C11 C18 108.52(14) . . ? C12 C11 C18 110.90(14) . . ? N1 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C18 C11 H11A 108.9 . . ? C17 C12 C13 118.51(16) . . ? C17 C12 C11 120.50(15) . . ? C13 C12 C11 120.99(15) . . ? C14 C13 C12 121.09(16) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C15 C14 C13 118.94(16) . . ? C15 C14 H14A 120.5 . . ? C13 C14 H14A 120.5 . . ? C14 C15 C16 121.21(16) . . ? C14 C15 Cl1 119.49(14) . . ? C16 C15 Cl1 119.30(14) . . ? C17 C16 C15 119.23(16) . . ? C17 C16 H16A 120.4 . . ? C15 C16 H16A 120.4 . . ? C16 C17 C12 121.01(16) . . ? C16 C17 H17A 119.5 . . ? C12 C17 H17A 119.5 . . ? C19 C18 C22 102.2(5) . . ? C19 C18 C11 117.0(4) . . ? C22 C18 C11 120.1(4) . . ? C19 C18 C22' 106.2(6) . . ? C11 C18 C22' 105.4(4) . . ? C22 C18 C19' 99.2(6) . . ? C11 C18 C19' 105.7(4) . . ? C22' C18 C19' 98.5(5) . . ? C19 C18 H18A 105.4 . . ? C22 C18 H18A 105.4 . . ? C11 C18 H18A 105.4 . . ? C22' C18 H18A 118.1 . . ? C19' C18 H18A 122.2 . . ? C19 C18 H18B 98.0 . . ? C22 C18 H18B 100.9 . . ? C11 C18 H18B 115.2 . . ? C22' C18 H18B 115.2 . . ? C19' C18 H18B 115.2 . . ? C20 C19 C18 107.6(6) . . ? C20 C19 H19A 126.2 . . ? C18 C19 H19A 126.2 . . ? C19 C20 C21 114.9(8) . . ? C19 C20 H20A 122.5 . . ? C21 C20 H20A 122.5 . . ? C20 C21 C22 101.0(9) . . ? C20 C21 H21A 111.6 . . ? C22 C21 H21A 111.6 . . ? C20 C21 H21B 111.6 . . ? C22 C21 H21B 111.6 . . ? H21A C21 H21B 109.4 . . ? C18 C22 C21 103.7(7) . . ? C18 C22 H22A 111.0 . . ? C21 C22 H22A 111.0 . . ? C18 C22 H22B 111.0 . . ? C21 C22 H22B 111.0 . . ? H22A C22 H22B 109.0 . . ? C20' C19' C18 107.8(7) . . ? C20' C19' H19B 110.1 . . ? C18 C19' H19B 110.1 . . ? C20' C19' H19C 110.1 . . ? C18 C19' H19C 110.1 . . ? H19B C19' H19C 108.5 . . ? C21' C20' C19' 100.3(10) . . ? C21' C20' H20B 111.7 . . ? C19' C20' H20B 111.7 . . ? C21' C20' H20C 111.7 . . ? C19' C20' H20C 111.7 . . ? H20B C20' H20C 109.5 . . ? C22' C21' C20' 115.5(11) . . ? C22' C21' H21C 122.2 . . ? C20' C21' H21C 122.2 . . ? C21' C22' C18 111.4(9) . . ? C21' C22' H22C 124.3 . . ? C18 C22' H22C 124.3 . . ? 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 N1 C1 C7 -66.29(18) . . . . ? C11 N1 C1 C6 176.25(14) . . . . ? C11 N1 C1 C2 56.96(19) . . . . ? N1 C1 C2 C3 176.15(14) . . . . ? C7 C1 C2 C3 -59.16(19) . . . . ? C6 C1 C2 C3 58.40(19) . . . . ? C1 C2 C3 C10 60.2(2) . . . . ? C1 C2 C3 C4 -60.28(19) . . . . ? C10 C3 C4 C5 -59.41(19) . . . . ? C2 C3 C4 C5 60.34(19) . . . . ? C3 C4 C5 C6 -59.83(19) . . . . ? C3 C4 C5 C9 59.72(19) . . . . ? C9 C5 C6 C1 -60.22(19) . . . . ? C4 C5 C6 C1 59.33(19) . . . . ? N1 C1 C6 C5 179.57(14) . . . . ? C7 C1 C6 C5 59.88(18) . . . . ? C2 C1 C6 C5 -58.15(18) . . . . ? N1 C1 C7 C8 -175.44(14) . . . . ? C6 C1 C7 C8 -59.20(18) . . . . ? C2 C1 C7 C8 58.76(18) . . . . ? C1 C7 C8 C9 60.35(19) . . . . ? C1 C7 C8 C10 -60.11(19) . . . . ? C10 C8 C9 C5 60.84(19) . . . . ? C7 C8 C9 C5 -59.64(19) . . . . ? C6 C5 C9 C8 59.1(2) . . . . ? C4 C5 C9 C8 -60.64(19) . . . . ? C4 C3 C10 C8 59.5(2) . . . . ? C2 C3 C10 C8 -60.5(2) . . . . ? C9 C8 C10 C3 -60.0(2) . . . . ? C7 C8 C10 C3 60.8(2) . . . . ? C1 N1 C11 C12 85.98(17) . . . . ? C1 N1 C11 C18 -152.03(15) . . . . ? N1 C11 C12 C17 45.0(2) . . . . ? C18 C11 C12 C17 -75.6(2) . . . . ? N1 C11 C12 C13 -135.84(16) . . . . ? C18 C11 C12 C13 103.57(19) . . . . ? C17 C12 C13 C14 -0.8(3) . . . . ? C11 C12 C13 C14 -179.97(16) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C13 C14 C15 Cl1 -179.35(14) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? Cl1 C15 C16 C17 179.40(14) . . . . ? C15 C16 C17 C12 -0.4(3) . . . . ? C13 C12 C17 C16 0.8(3) . . . . ? C11 C12 C17 C16 -179.97(16) . . . . ? N1 C11 C18 C19 54.4(4) . . . . ? C12 C11 C18 C19 176.4(4) . . . . ? N1 C11 C18 C22 179.2(5) . . . . ? C12 C11 C18 C22 -58.9(5) . . . . ? N1 C11 C18 C22' 172.1(5) . . . . ? C12 C11 C18 C22' -66.0(5) . . . . ? N1 C11 C18 C19' 68.4(4) . . . . ? C12 C11 C18 C19' -169.6(4) . . . . ? C22 C18 C19 C20 -26.6(10) . . . . ? C11 C18 C19 C20 106.7(8) . . . . ? C22' C18 C19 C20 -10.5(11) . . . . ? C19' C18 C19 C20 54.8(19) . . . . ? C18 C19 C20 C21 10.1(13) . . . . ? C19 C20 C21 C22 10.7(13) . . . . ? C19 C18 C22 C21 32.2(9) . . . . ? C11 C18 C22 C21 -99.2(8) . . . . ? C22' C18 C22 C21 -74(3) . . . . ? C19' C18 C22 C21 15.0(9) . . . . ? C20 C21 C22 C18 -26.3(10) . . . . ? C19 C18 C19' C20' -93(2) . . . . ? C22 C18 C19' C20' 8.6(8) . . . . ? C11 C18 C19' C20' 133.6(6) . . . . ? C22' C18 C19' C20' 24.9(9) . . . . ? C18 C19' C20' C21' -22.8(9) . . . . ? C19' C20' C21' C22' 11.5(14) . . . . ? C20' C21' C22' C18 4.9(16) . . . . ? C19 C18 C22' C21' -2.7(13) . . . . ? C22 C18 C22' C21' 75(3) . . . . ? C11 C18 C22' C21' -127.4(10) . . . . ? C19' C18 C22' C21' -18.5(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.246 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.046 data_ma0503 _database_code_depnum_ccdc_archive 'CCDC 840703' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H30 Cl N' _chemical_formula_sum 'C23 H30 Cl N' _chemical_formula_weight 355.93 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)/c _symmetry_space_group_name_Hall -P2ybc 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 9.6458(8) _cell_length_b 15.645(2) _cell_length_c 12.6055(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.295(6) _cell_angle_gamma 90.00 _cell_volume 1901.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 166 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.938 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS, Bruker AXS, 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method ; \w-rotations with 2.00 \% and 220 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 47950 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 27.10 _reflns_number_total 4184 _reflns_number_gt 3304 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Duisenberg, 2003)' _computing_data_reduction 'EVALCCD (Duisenberg, 2003)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _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. N1 bound hydrogen atom H1A positional parameters have been taken from a difference fourier synthesis as its position obviously deviates from the tentative geometrical position. The cyclohexene ring is disordered indicating the existence of two diastereomers within the crystal. The ratio of the two diastereomers has been refined to give 70.6(7):29.4(7). The crystal structure thus contains two enantiomeric pairs of diastereomers. The adamantane group is also disordered. Again two positions could be refined with a ratio of their occupancy factors of 91.1(2):8.9(2). A number of SADI and SIMU restraints have been applied in the refinement of the disordered parts of the structure. ; _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^)+(0.0374P)^2^+1.5074P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom except H1A difmap' _refine_ls_hydrogen_treatment 'constr except H1A refxyz' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4184 _refine_ls_number_parameters 320 _refine_ls_number_restraints 163 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.086 _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 0.85662(5) 0.10535(3) 0.94369(3) 0.03167(15) Uani 1 1 d . A . N1 N 0.51024(17) 0.12807(11) 0.47623(13) 0.0206(4) Uani 0.911(2) 1 d PD A 1 H1A H 0.480(2) 0.0943(15) 0.5336(18) 0.025 Uiso 0.911(2) 1 d P A 1 C1 C 0.4332(2) 0.20969(13) 0.47400(15) 0.0192(4) Uani 0.911(2) 1 d PD A 1 C2 C 0.4513(2) 0.25356(14) 0.36655(16) 0.0261(5) Uani 0.911(2) 1 d PD A 1 H2A H 0.4217 0.2143 0.3087 0.031 Uiso 0.911(2) 1 calc PR A 1 H2B H 0.5503 0.2676 0.3570 0.031 Uiso 0.911(2) 1 calc PR A 1 C3 C 0.3639(2) 0.33604(16) 0.36087(19) 0.0333(5) Uani 0.911(2) 1 d PD A 1 H3A H 0.3773 0.3644 0.2907 0.040 Uiso 0.911(2) 1 calc PR A 1 C4 C 0.2110(3) 0.31345(18) 0.3723(2) 0.0315(6) Uani 0.911(2) 1 d PD A 1 H4A H 0.1810 0.2746 0.3142 0.038 Uiso 0.911(2) 1 calc PR A 1 H4B H 0.1539 0.3660 0.3676 0.038 Uiso 0.911(2) 1 calc PR A 1 C5 C 0.1906(2) 0.26979(17) 0.4800(2) 0.0301(5) Uani 0.911(2) 1 d PD A 1 H5A H 0.0906 0.2546 0.4879 0.036 Uiso 0.911(2) 1 calc PR A 1 C6 C 0.2794(2) 0.18836(14) 0.48660(18) 0.0280(5) Uani 0.911(2) 1 d PD A 1 H6A H 0.2660 0.1602 0.5559 0.034 Uiso 0.911(2) 1 calc PR A 1 H6B H 0.2492 0.1481 0.4301 0.034 Uiso 0.911(2) 1 calc PR A 1 C7 C 0.4769(2) 0.27213(16) 0.56314(16) 0.0253(5) Uani 0.911(2) 1 d PD A 1 H7A H 0.4647 0.2445 0.6330 0.030 Uiso 0.911(2) 1 calc PR A 1 H7B H 0.5762 0.2869 0.5566 0.030 Uiso 0.911(2) 1 calc PR A 1 C8 C 0.3892(2) 0.35367(15) 0.55646(19) 0.0341(6) Uani 0.911(2) 1 d PD A 1 H8A H 0.4192 0.3936 0.6145 0.041 Uiso 0.911(2) 1 calc PR A 1 C9 C 0.2357(2) 0.33167(16) 0.56877(18) 0.0342(6) Uani 0.911(2) 1 d PD A 1 H9A H 0.1792 0.3844 0.5646 0.041 Uiso 0.911(2) 1 calc PR A 1 H9B H 0.2215 0.3049 0.6388 0.041 Uiso 0.911(2) 1 calc PR A 1 C10 C 0.4098(3) 0.39663(16) 0.4495(2) 0.0389(6) Uani 0.911(2) 1 d PD A 1 H10A H 0.3548 0.4500 0.4453 0.047 Uiso 0.911(2) 1 calc PR A 1 H10B H 0.5088 0.4116 0.4416 0.047 Uiso 0.911(2) 1 calc PR A 1 C11 C 0.66239(18) 0.13245(12) 0.48490(13) 0.0222(4) Uani 1 1 d D . . H11A H 0.6901 0.1903 0.4590 0.027 Uiso 0.706(7) 1 calc PR A 1 H11B H 0.5698 0.1045 0.4920 0.027 Uiso 0.294(7) 1 d PR A 2 C12 C 0.71556(18) 0.12502(11) 0.59930(13) 0.0189(4) Uani 1 1 d . A . C13 C 0.80206(19) 0.18670(12) 0.64469(14) 0.0229(4) Uani 1 1 d . . . H13A H 0.8308 0.2337 0.6029 0.028 Uiso 1 1 calc R A . C14 C 0.84741(19) 0.18111(12) 0.74996(14) 0.0242(4) Uani 1 1 d . A . H14A H 0.9068 0.2236 0.7799 0.029 Uiso 1 1 calc R . . C15 C 0.80445(18) 0.11264(12) 0.81016(13) 0.0217(4) Uani 1 1 d . . . C16 C 0.72019(19) 0.04940(12) 0.76714(14) 0.0231(4) Uani 1 1 d . A . H16A H 0.6926 0.0022 0.8091 0.028 Uiso 1 1 calc R . . C17 C 0.67646(18) 0.05591(12) 0.66158(14) 0.0218(4) Uani 1 1 d . . . H17A H 0.6190 0.0125 0.6314 0.026 Uiso 1 1 calc R A . C18 C 0.7325(2) 0.06626(13) 0.41291(14) 0.0271(4) Uani 1 1 d . A . H18A H 0.7056 0.0074 0.4357 0.032 Uiso 0.706(7) 1 calc PR A 1 H18B H 0.7206 0.0110 0.4516 0.032 Uiso 0.294(7) 1 d PR A 2 C19 C 0.6799(4) 0.0814(2) 0.2971(3) 0.0205(8) Uani 0.706(7) 1 d PDU A 1 H19A H 0.5829 0.0892 0.2862 0.025 Uiso 0.706(7) 1 calc PR A 1 C20 C 0.7538(5) 0.0844(3) 0.2169(4) 0.0284(9) Uani 0.706(7) 1 d PDU A 1 H20A H 0.7121 0.0997 0.1506 0.034 Uiso 0.706(7) 1 calc PR A 1 C21 C 0.9131(11) 0.0636(6) 0.2219(9) 0.0301(14) Uani 0.706(7) 1 d PU A 1 H21A H 0.9354 0.0221 0.1654 0.036 Uiso 0.706(7) 1 calc PR A 1 H21B H 0.9668 0.1165 0.2094 0.036 Uiso 0.706(7) 1 calc PR A 1 C22 C 0.9538(4) 0.0267(3) 0.3290(2) 0.0409(10) Uani 0.706(7) 1 d PDU A 1 H22A H 1.0557 0.0300 0.3391 0.049 Uiso 0.706(7) 1 calc PR A 1 H22B H 0.9267 -0.0343 0.3313 0.049 Uiso 0.706(7) 1 calc PR A 1 C23 C 0.8847(12) 0.0744(9) 0.4186(7) 0.0343(15) Uani 0.706(7) 1 d PDU A 1 H23A H 0.9195 0.0515 0.4875 0.041 Uiso 0.706(7) 1 calc PR A 1 H23B H 0.9102 0.1356 0.4152 0.041 Uiso 0.706(7) 1 calc PR A 1 C19' C 0.6771(14) 0.0469(8) 0.3069(10) 0.037(2) Uani 0.294(7) 1 d PDU A 2 H19B H 0.6410 -0.0123 0.3073 0.045 Uiso 0.294(7) 1 calc PR A 2 H19C H 0.5974 0.0853 0.2923 0.045 Uiso 0.294(7) 1 calc PR A 2 C20' C 0.7710(14) 0.0546(9) 0.2213(10) 0.041(2) Uani 0.294(7) 1 d PDU A 2 H20B H 0.7691 -0.0024 0.1871 0.049 Uiso 0.294(7) 1 calc PR A 2 H20C H 0.7232 0.0935 0.1704 0.049 Uiso 0.294(7) 1 calc PR A 2 C21' C 0.905(3) 0.0784(16) 0.219(2) 0.032(2) Uani 0.294(7) 1 d PU A 2 H21C H 0.9111 0.1353 0.1848 0.038 Uiso 0.294(7) 1 calc PR A 2 H21D H 0.9563 0.0373 0.1749 0.038 Uiso 0.294(7) 1 calc PR A 2 C22' C 0.9721(7) 0.0824(6) 0.3309(5) 0.0257(16) Uani 0.294(7) 1 d PDU A 2 H22C H 1.0700 0.0878 0.3382 0.031 Uiso 0.294(7) 1 calc PR A 2 C23' C 0.900(3) 0.078(2) 0.4131(19) 0.035(3) Uani 0.294(7) 1 d PDU A 2 H23C H 0.9472 0.0829 0.4799 0.041 Uiso 0.294(7) 1 calc PR A 2 N1' N 0.6223(14) 0.2097(7) 0.4390(12) 0.023(4) Uiso 0.089(2) 1 d PD A 2 H1'A H 0.6818 0.2412 0.4042 0.027 Uiso 0.089(2) 1 calc PR A 2 C1' C 0.4787(15) 0.2372(10) 0.4501(13) 0.017(5) Uiso 0.089(2) 1 d PD A 2 C2' C 0.3723(16) 0.1869(11) 0.3850(14) 0.026(5) Uiso 0.089(2) 1 d PD A 2 H2'A H 0.3641 0.1282 0.4133 0.031 Uiso 0.089(2) 1 calc PR A 2 H2'B H 0.4010 0.1833 0.3102 0.031 Uiso 0.089(2) 1 calc PR A 2 C3' C 0.2314(17) 0.2339(11) 0.3916(14) 0.029(5) Uiso 0.089(2) 1 d PD A 2 H3'A H 0.1595 0.2032 0.3479 0.035 Uiso 0.089(2) 1 calc PR A 2 C4' C 0.189(2) 0.2360(15) 0.5062(15) 0.030(7) Uiso 0.089(2) 1 d PD A 2 H4'A H 0.1844 0.1770 0.5342 0.037 Uiso 0.089(2) 1 calc PR A 2 H4'B H 0.0963 0.2622 0.5114 0.037 Uiso 0.089(2) 1 calc PR A 2 C5' C 0.2962(19) 0.2886(12) 0.5733(15) 0.034(6) Uiso 0.089(2) 1 d PD A 2 H5'A H 0.2662 0.2918 0.6486 0.040 Uiso 0.089(2) 1 calc PR A 2 C6' C 0.4359(18) 0.2398(13) 0.5674(12) 0.016(5) Uiso 0.089(2) 1 d PD A 2 H6'A H 0.5079 0.2693 0.6109 0.019 Uiso 0.089(2) 1 calc PR A 2 H6'B H 0.4252 0.1810 0.5950 0.019 Uiso 0.089(2) 1 calc PR A 2 C7' C 0.4948(17) 0.3287(10) 0.4074(16) 0.029(5) Uiso 0.089(2) 1 d PD A 2 H7'A H 0.5659 0.3597 0.4503 0.035 Uiso 0.089(2) 1 calc PR A 2 H7'B H 0.5255 0.3268 0.3330 0.035 Uiso 0.089(2) 1 calc PR A 2 C8' C 0.3580(17) 0.3742(11) 0.4130(14) 0.015(4) Uiso 0.089(2) 1 d PD A 2 H8'A H 0.3659 0.4334 0.3838 0.018 Uiso 0.089(2) 1 calc PR A 2 C9' C 0.312(3) 0.3773(12) 0.5288(15) 0.037(6) Uiso 0.089(2) 1 d PD A 2 H9'A H 0.3822 0.4091 0.5720 0.045 Uiso 0.089(2) 1 calc PR A 2 H9'B H 0.2230 0.4082 0.5328 0.045 Uiso 0.089(2) 1 calc PR A 2 C10' C 0.251(2) 0.3234(13) 0.3495(18) 0.026(8) Uiso 0.089(2) 1 d PD A 2 H10C H 0.1606 0.3538 0.3509 0.031 Uiso 0.089(2) 1 calc PR A 2 H10D H 0.2792 0.3201 0.2747 0.031 Uiso 0.089(2) 1 calc PR A 2 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 0.0343(3) 0.0462(3) 0.0144(2) 0.0025(2) -0.00256(17) -0.0066(2) N1 0.0174(8) 0.0239(9) 0.0205(8) 0.0012(7) 0.0005(6) 0.0006(7) C1 0.0199(10) 0.0222(10) 0.0156(9) -0.0013(8) 0.0025(8) 0.0004(8) C2 0.0256(11) 0.0331(12) 0.0198(10) 0.0026(9) 0.0049(8) 0.0065(9) C3 0.0332(13) 0.0365(13) 0.0303(12) 0.0105(11) 0.0058(10) 0.0092(10) C4 0.0264(13) 0.0379(15) 0.0301(13) -0.0013(11) -0.0031(12) 0.0106(11) C5 0.0182(11) 0.0345(14) 0.0376(13) -0.0003(12) 0.0033(9) 0.0023(10) C6 0.0213(10) 0.0301(12) 0.0327(11) -0.0013(9) 0.0029(8) -0.0005(9) C7 0.0236(11) 0.0313(13) 0.0210(10) -0.0091(9) -0.0001(8) 0.0034(11) C8 0.0297(12) 0.0354(13) 0.0371(13) -0.0176(10) -0.0023(10) 0.0065(10) C9 0.0320(12) 0.0409(14) 0.0300(12) -0.0071(10) 0.0064(9) 0.0135(11) C10 0.0299(12) 0.0243(12) 0.0626(17) 0.0013(12) 0.0037(12) 0.0027(10) C11 0.0196(9) 0.0313(10) 0.0157(8) -0.0011(7) 0.0016(7) 0.0039(8) C12 0.0182(8) 0.0234(9) 0.0153(8) -0.0011(7) 0.0031(6) 0.0051(7) C13 0.0269(10) 0.0224(9) 0.0196(9) 0.0035(7) 0.0016(7) -0.0012(8) C14 0.0255(9) 0.0250(10) 0.0221(9) -0.0016(7) -0.0012(7) -0.0034(8) C15 0.0227(9) 0.0292(10) 0.0131(8) -0.0004(7) 0.0016(7) 0.0010(8) C16 0.0247(9) 0.0263(10) 0.0184(8) 0.0043(7) 0.0031(7) -0.0025(8) C17 0.0221(9) 0.0232(9) 0.0201(8) -0.0033(7) 0.0014(7) -0.0015(7) C18 0.0299(10) 0.0339(11) 0.0176(9) -0.0045(8) 0.0047(7) 0.0017(8) C19 0.0204(14) 0.025(2) 0.0165(14) -0.0029(16) -0.0023(11) 0.0007(16) C20 0.0283(17) 0.033(2) 0.0241(15) 0.0150(17) -0.0062(13) -0.0012(16) C21 0.029(2) 0.041(3) 0.021(2) 0.000(2) 0.0101(17) 0.007(2) C22 0.0296(16) 0.067(3) 0.0261(15) -0.0022(17) 0.0042(12) 0.0194(18) C23 0.024(3) 0.065(3) 0.0144(19) -0.0071(19) 0.0053(18) 0.016(3) C19' 0.040(4) 0.046(5) 0.025(4) 0.001(5) 0.005(3) -0.006(5) C20' 0.042(4) 0.057(5) 0.022(3) -0.006(4) -0.003(3) 0.000(4) C21' 0.032(4) 0.046(5) 0.018(4) 0.000(4) -0.004(3) 0.002(4) C22' 0.017(3) 0.039(4) 0.021(3) -0.007(3) -0.003(2) 0.006(3) C23' 0.015(5) 0.062(5) 0.026(5) 0.000(5) -0.008(4) 0.008(4) _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 C15 1.7496(17) . ? N1 C11 1.471(2) . ? N1 C1 1.477(2) . ? N1 H1A 0.95(2) . ? N1 H11B 0.7078 . ? C1 C2 1.532(3) . ? C1 C6 1.533(3) . ? C1 C7 1.540(3) . ? C2 C3 1.542(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C10 1.523(4) . ? C3 C4 1.527(4) . ? C3 H3A 1.0000 . ? C4 C5 1.537(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C9 1.535(3) . ? C5 C6 1.536(3) . ? C5 H5A 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.532(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.524(4) . ? C8 C9 1.531(3) . ? C8 H8A 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N1' 1.392(9) . ? C11 C12 1.524(2) . ? C11 C18 1.543(2) . ? C11 H11A 1.0000 . ? C11 H11B 1.0000 . ? C12 C13 1.390(3) . ? C12 C17 1.393(2) . ? C13 C14 1.391(2) . ? C13 H13A 0.9500 . ? C14 C15 1.382(3) . ? C14 H14A 0.9500 . ? C15 C16 1.383(3) . ? C16 C17 1.390(2) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 C19' 1.460(13) . ? C18 C23 1.474(12) . ? C18 C19 1.552(5) . ? C18 C23' 1.63(3) . ? C18 H18A 1.0000 . ? C18 H18B 1.0000 . ? C19 C20 1.252(6) . ? C19 H19A 0.9500 . ? C20 C21 1.571(12) . ? C20 H20A 0.9500 . ? C21 C22 1.513(11) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.520(9) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C19' C20' 1.430(14) . ? C19' H19B 0.9900 . ? C19' H19C 0.9900 . ? C20' C21' 1.34(3) . ? C20' H20B 0.9900 . ? C20' H20C 0.9900 . ? C21' C22' 1.55(3) . ? C21' H21C 0.9900 . ? C21' H21D 0.9900 . ? C22' C23' 1.261(18) . ? C22' H22C 0.9500 . ? C23' H23C 0.9500 . ? N1' C1' 1.460(15) . ? N1' H1'A 0.8800 . ? C1' C2' 1.520(16) . ? C1' C7' 1.538(17) . ? C1' C6' 1.544(16) . ? C2' C3' 1.549(16) . ? C2' H2'A 0.9900 . ? C2' H2'B 0.9900 . ? C3' C4' 1.509(17) . ? C3' C10' 1.510(17) . ? C3' H3'A 1.0000 . ? C4' C5' 1.554(18) . ? C4' H4'A 0.9900 . ? C4' H4'B 0.9900 . ? C5' C9' 1.507(17) . ? C5' C6' 1.551(17) . ? C5' H5'A 1.0000 . ? C6' H6'A 0.9900 . ? C6' H6'B 0.9900 . ? C7' C8' 1.503(16) . ? C7' H7'A 0.9900 . ? C7' H7'B 0.9900 . ? C8' C10' 1.520(18) . ? C8' C9' 1.535(17) . ? C8' H8'A 1.0000 . ? C9' H9'A 0.9900 . ? C9' H9'B 0.9900 . ? C10' H10C 0.9900 . ? C10' H10D 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 N1 C1 117.49(16) . . ? C11 N1 H1A 107.0(14) . . ? C1 N1 H1A 109.6(13) . . ? C1 N1 H11B 149.4 . . ? H1A N1 H11B 75.9 . . ? N1 C1 C2 109.70(15) . . ? N1 C1 C6 107.30(17) . . ? C2 C1 C6 108.59(16) . . ? N1 C1 C7 113.90(16) . . ? C2 C1 C7 109.03(19) . . ? C6 C1 C7 108.18(17) . . ? C1 C2 C3 110.07(16) . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.2 . . ? C10 C3 C4 109.9(2) . . ? C10 C3 C2 109.69(18) . . ? C4 C3 C2 109.3(2) . . ? C10 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? C3 C4 C5 109.24(18) . . ? C3 C4 H4A 109.8 . . ? C5 C4 H4A 109.8 . . ? C3 C4 H4B 109.8 . . ? C5 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? C9 C5 C6 109.57(19) . . ? C9 C5 C4 108.9(2) . . ? C6 C5 C4 109.49(19) . . ? C9 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? C1 C6 C5 110.72(18) . . ? C1 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C1 110.27(17) . . ? C8 C7 H7A 109.6 . . ? C1 C7 H7A 109.6 . . ? C8 C7 H7B 109.6 . . ? C1 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C10 C8 C9 109.6(2) . . ? C10 C8 C7 109.44(18) . . ? C9 C8 C7 110.0(2) . . ? C10 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? C8 C9 C5 109.09(17) . . ? C8 C9 H9A 109.9 . . ? C5 C9 H9A 109.9 . . ? C8 C9 H9B 109.9 . . ? C5 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? C3 C10 C8 109.4(2) . . ? C3 C10 H10A 109.8 . . ? C8 C10 H10A 109.8 . . ? C3 C10 H10B 109.8 . . ? C8 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? N1' C11 N1 75.1(6) . . ? N1' C11 C12 123.0(7) . . ? N1 C11 C12 112.37(14) . . ? N1' C11 C18 117.4(7) . . ? N1 C11 C18 112.01(15) . . ? C12 C11 C18 111.27(15) . . ? N1 C11 H11A 106.9 . . ? C12 C11 H11A 106.9 . . ? C18 C11 H11A 106.9 . . ? N1' C11 H11B 100.2 . . ? C12 C11 H11B 99.4 . . ? C18 C11 H11B 99.4 . . ? H11A C11 H11B 132.1 . . ? C13 C12 C17 118.32(16) . . ? C13 C12 C11 121.49(16) . . ? C17 C12 C11 120.18(16) . . ? C12 C13 C14 121.46(17) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 118.75(17) . . ? C15 C14 H14A 120.6 . . ? C13 C14 H14A 120.6 . . ? C14 C15 C16 121.33(16) . . ? C14 C15 Cl1 119.71(14) . . ? C16 C15 Cl1 118.96(14) . . ? C15 C16 C17 119.05(16) . . ? C15 C16 H16A 120.5 . . ? C17 C16 H16A 120.5 . . ? C16 C17 C12 121.06(17) . . ? C16 C17 H17A 119.5 . . ? C12 C17 H17A 119.5 . . ? C19' C18 C23 114.0(6) . . ? C19' C18 C11 121.4(6) . . ? C23 C18 C11 111.3(5) . . ? C23 C18 C19 109.7(4) . . ? C11 C18 C19 108.2(2) . . ? C19' C18 C23' 111.6(9) . . ? C11 C18 C23' 111.7(11) . . ? C19 C18 C23' 106.7(9) . . ? C19' C18 H18A 88.9 . . ? C23 C18 H18A 109.2 . . ? C11 C18 H18A 109.2 . . ? C19 C18 H18A 109.2 . . ? C23' C18 H18A 111.8 . . ? C19' C18 H18B 102.9 . . ? C23 C18 H18B 100.1 . . ? C11 C18 H18B 103.7 . . ? C19 C18 H18B 123.5 . . ? C23' C18 H18B 103.0 . . ? C20 C19 C18 125.8(4) . . ? C20 C19 H19A 117.1 . . ? C18 C19 H19A 117.1 . . ? C19 C20 C21 122.3(6) . . ? C19 C20 H20A 118.8 . . ? C21 C20 H20A 118.8 . . ? C22 C21 C20 110.4(7) . . ? C22 C21 H21A 109.6 . . ? C20 C21 H21A 109.6 . . ? C22 C21 H21B 109.6 . . ? C20 C21 H21B 109.6 . . ? H21A C21 H21B 108.1 . . ? C21 C22 C23 111.6(6) . . ? C21 C22 H22A 109.3 . . ? C23 C22 H22A 109.3 . . ? C21 C22 H22B 109.3 . . ? C23 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? C18 C23 C22 112.0(8) . . ? C18 C23 H23A 109.2 . . ? C22 C23 H23A 109.2 . . ? C18 C23 H23B 109.2 . . ? C22 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C20' C19' C18 116.7(10) . . ? C20' C19' H19B 108.1 . . ? C18 C19' H19B 108.1 . . ? C20' C19' H19C 108.1 . . ? C18 C19' H19C 108.1 . . ? H19B C19' H19C 107.3 . . ? C21' C20' C19' 131.8(18) . . ? C21' C20' H20B 104.3 . . ? C19' C20' H20B 104.3 . . ? C21' C20' H20C 104.3 . . ? C19' C20' H20C 104.3 . . ? H20B C20' H20C 105.6 . . ? C20' C21' C22' 112(2) . . ? C20' C21' H21C 109.2 . . ? C22' C21' H21C 109.2 . . ? C20' C21' H21D 109.2 . . ? C22' C21' H21D 109.2 . . ? H21C C21' H21D 107.9 . . ? C23' C22' C21' 121.5(18) . . ? C23' C22' H22C 119.3 . . ? C21' C22' H22C 119.3 . . ? C22' C23' C18 125(2) . . ? C22' C23' H23C 117.6 . . ? C18 C23' H23C 117.6 . . ? C11 N1' C1' 118.1(11) . . ? C11 N1' H1'A 121.0 . . ? C1' N1' H1'A 121.0 . . ? N1' C1' C2' 115.2(13) . . ? N1' C1' C7' 97.8(11) . . ? C2' C1' C7' 111.4(14) . . ? N1' C1' C6' 112.0(12) . . ? C2' C1' C6' 109.8(14) . . ? C7' C1' C6' 110.0(13) . . ? C1' C2' C3' 107.9(12) . . ? C1' C2' H2'A 110.1 . . ? C3' C2' H2'A 110.1 . . ? C1' C2' H2'B 110.1 . . ? C3' C2' H2'B 110.1 . . ? H2'A C2' H2'B 108.4 . . ? C4' C3' C10' 110.7(16) . . ? C4' C3' C2' 108.5(15) . . ? C10' C3' C2' 107.9(15) . . ? C4' C3' H3'A 109.9 . . ? C10' C3' H3'A 109.9 . . ? C2' C3' H3'A 109.9 . . ? C3' C4' C5' 110.1(14) . . ? C3' C4' H4'A 109.6 . . ? C5' C4' H4'A 109.6 . . ? C3' C4' H4'B 109.6 . . ? C5' C4' H4'B 109.6 . . ? H4'A C4' H4'B 108.2 . . ? C9' C5' C6' 109.8(15) . . ? C9' C5' C4' 111.0(16) . . ? C6' C5' C4' 106.3(15) . . ? C9' C5' H5'A 109.9 . . ? C6' C5' H5'A 109.9 . . ? C4' C5' H5'A 109.9 . . ? C1' C6' C5' 108.1(12) . . ? C1' C6' H6'A 110.1 . . ? C5' C6' H6'A 110.1 . . ? C1' C6' H6'B 110.1 . . ? C5' C6' H6'B 110.1 . . ? H6'A C6' H6'B 108.4 . . ? C8' C7' C1' 109.2(13) . . ? C8' C7' H7'A 109.8 . . ? C1' C7' H7'A 109.8 . . ? C8' C7' H7'B 109.8 . . ? C1' C7' H7'B 109.8 . . ? H7'A C7' H7'B 108.3 . . ? C7' C8' C10' 108.5(16) . . ? C7' C8' C9' 109.3(14) . . ? C10' C8' C9' 108.1(15) . . ? C7' C8' H8'A 110.3 . . ? C10' C8' H8'A 110.3 . . ? C9' C8' H8'A 110.3 . . ? C5' C9' C8' 111.0(14) . . ? C5' C9' H9'A 109.4 . . ? C8' C9' H9'A 109.4 . . ? C5' C9' H9'B 109.4 . . ? C8' C9' H9'B 109.4 . . ? H9'A C9' H9'B 108.0 . . ? C3' C10' C8' 112.8(15) . . ? C3' C10' H10C 109.0 . . ? C8' C10' H10C 109.0 . . ? C3' C10' H10D 109.0 . . ? C8' C10' H10D 109.0 . . ? H10C C10' H10D 107.8 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.375 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.046 data_ma0501 _database_code_depnum_ccdc_archive 'CCDC 840704' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H42 Cl2 N2' _chemical_formula_weight 549.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) _symmetry_space_group_name_Hall P2c-2n _chemical_absolute_configuration unk 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 11.276(1) _cell_length_b 12.100(1) _cell_length_c 20.803(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2838.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 296 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.968 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS, Bruker AXS, 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method ; \f- and \w-rotations with 1.60 \% and 48 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35712 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 27.88 _reflns_number_total 6674 _reflns_number_gt 5226 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Duisenberg, 2003)' _computing_data_reduction 'EVALCCD (Duisenberg, 2003)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _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. A structure solution in the corresponding centrosymmetric space group Pnma was not successful. The structure could be solved in Pbcn which is a non- isomorphic supergroup of Pna2(1). The structure solution in Pbcn revealed a molecule with crystallographic C2 symmetry with the apparent twofold axis being perpendicular to the central C-C bond (C11-C28).The refinement in Pbcn, however, resulted in significant differences between F(o) and F(c) values for all of the 'most disagreeable' reflections having F(o) much greater than F(c). This is a typical 'warning sign' for twinning and corresponded with the high final R values. Therefore, a solution and refinement in Pna2(1) was successfully attempted and resulted in R values being about two times lower than for Pbcn and showing no longer the above mentioned F(o)>>F(c) differences. While the refinement in Pna2(1) showed still a well approximated twofold symmetry, the symmetry breaking is achieved by the N-H protons that are not related by a twofold axis. A number of crystals has been investigated showing all the same behaviour. All of these crystals turned out to be inversion twins and the twin component ratio refined was in the range 62:38 to 50:50 as was observed for the present structure determination. ; _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^)+(0.0369P)^2^+0.6034P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; Flack H D (1983), Acta Cryst. A39, 876-881 3218 Friedel pairs used in the refinement of Flack parameter ; _refine_ls_abs_structure_Flack 0.49(7) _refine_ls_number_reflns 6674 _refine_ls_number_parameters 470 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.50862(6) 0.21672(6) 0.64947(4) 0.02486(19) Uani 1 1 d . . . Cl2 Cl 0.98091(5) 0.22003(6) 0.83861(4) 0.02320(19) Uani 1 1 d . . . N1 N 0.66258(19) 0.7622(2) 0.69182(13) 0.0110(5) Uani 1 1 d . . . H1N H 0.589(2) 0.7510(18) 0.6998(10) 0.013 Uiso 1 1 d . . . N2 N 0.82797(18) 0.7595(2) 0.79597(12) 0.0117(5) Uani 1 1 d . . . H2N H 0.8085(18) 0.8113(18) 0.7681(11) 0.014 Uiso 1 1 d . . . C1 C 0.6805(2) 0.8145(2) 0.62807(15) 0.0128(6) Uani 1 1 d . . . C2 C 0.8045(2) 0.8625(3) 0.62547(16) 0.0144(6) Uani 1 1 d . . . H2A H 0.866(2) 0.800(2) 0.6220(16) 0.017 Uiso 1 1 d . . . H2B H 0.812(2) 0.915(2) 0.6622(15) 0.017 Uiso 1 1 d . . . C3 C 0.8235(2) 0.9259(3) 0.56165(18) 0.0198(7) Uani 1 1 d . . . H3 H 0.906(3) 0.953(2) 0.5621(14) 0.024 Uiso 1 1 d . . . C4 C 0.7334(2) 1.0207(3) 0.55753(17) 0.0179(7) Uani 1 1 d . . . H4A H 0.744(2) 1.068(3) 0.5907(18) 0.022 Uiso 1 1 d . . . H4B H 0.743(2) 1.067(2) 0.5144(17) 0.022 Uiso 1 1 d . . . C5 C 0.6079(2) 0.9733(3) 0.55888(16) 0.0139(6) Uani 1 1 d . . . H5 H 0.554(2) 1.030(3) 0.5565(16) 0.017 Uiso 1 1 d . . . C6 C 0.5905(2) 0.9093(3) 0.62261(16) 0.0147(6) Uani 1 1 d . . . H6A H 0.504(2) 0.878(2) 0.6243(14) 0.018 Uiso 1 1 d . . . H6B H 0.5965(19) 0.958(2) 0.6600(15) 0.018 Uiso 1 1 d . . . C7 C 0.6623(2) 0.7359(3) 0.57073(16) 0.0142(7) Uani 1 1 d . . . H7A H 0.718(2) 0.682(2) 0.5755(16) 0.017 Uiso 1 1 d . . . H7B H 0.582(3) 0.708(2) 0.5739(16) 0.017 Uiso 1 1 d . . . C8 C 0.6793(2) 0.7996(3) 0.50693(16) 0.0150(7) Uani 1 1 d . . . H8B H 0.673(2) 0.750(2) 0.4715(16) 0.018 Uiso 1 1 d . . . C9 C 0.5899(2) 0.8932(3) 0.50214(16) 0.0143(7) Uani 1 1 d . . . H9A H 0.509(2) 0.861(3) 0.5033(15) 0.017 Uiso 1 1 d . . . H9B H 0.601(2) 0.932(3) 0.4658(17) 0.017 Uiso 1 1 d . . . C10 C 0.8058(3) 0.8473(3) 0.50546(18) 0.0212(8) Uani 1 1 d . . . H10A H 0.867(3) 0.789(2) 0.5093(14) 0.025 Uiso 1 1 d . . . H10B H 0.817(2) 0.891(3) 0.4657(18) 0.025 Uiso 1 1 d . . . C11 C 0.7289(2) 0.6617(2) 0.70745(15) 0.0111(6) Uani 1 1 d . . . H1 H 0.808(2) 0.671(2) 0.6859(15) 0.013 Uiso 1 1 d . . . C12 C 0.6714(2) 0.5527(2) 0.68867(14) 0.0088(6) Uani 1 1 d . . . C13 C 0.7390(2) 0.4666(3) 0.66266(16) 0.0150(6) Uani 1 1 d . . . H13 H 0.825(2) 0.480(2) 0.6501(14) 0.018 Uiso 1 1 d . . . C14 C 0.6902(2) 0.3637(3) 0.65125(17) 0.0149(6) Uani 1 1 d . . . H14 H 0.742(2) 0.298(2) 0.6326(15) 0.018 Uiso 1 1 d . . . C15 C 0.5712(2) 0.3452(3) 0.66430(16) 0.0155(7) Uani 1 1 d . . . C16 C 0.5015(2) 0.4293(3) 0.69032(16) 0.0126(6) Uani 1 1 d . . . H16 H 0.421(2) 0.412(2) 0.6991(15) 0.015 Uiso 1 1 d . . . C17 C 0.5523(2) 0.5326(2) 0.70222(15) 0.0136(6) Uani 1 1 d . . . H17 H 0.504(2) 0.591(2) 0.7245(12) 0.016 Uiso 1 1 d . . . C18 C 0.8109(2) 0.8131(2) 0.85947(15) 0.0092(6) Uani 1 1 d . . . C19 C 0.6833(2) 0.8609(3) 0.86723(18) 0.0162(7) Uani 1 1 d . . . H19A H 0.627(2) 0.803(3) 0.8603(16) 0.019 Uiso 1 1 d . . . H19B H 0.666(2) 0.909(2) 0.8302(16) 0.019 Uiso 1 1 d . . . C20 C 0.6696(2) 0.9221(3) 0.93086(16) 0.0166(7) Uani 1 1 d . . . H20 H 0.588(2) 0.951(2) 0.9366(13) 0.020 Uiso 1 1 d . . . C21 C 0.7567(2) 1.0186(3) 0.93340(19) 0.0197(7) Uani 1 1 d . . . H21A H 0.743(2) 1.073(3) 0.8949(18) 0.024 Uiso 1 1 d . . . H21B H 0.744(2) 1.052(2) 0.9731(18) 0.024 Uiso 1 1 d . . . C22 C 0.8843(2) 0.9748(3) 0.92585(16) 0.0165(6) Uani 1 1 d . . . H22 H 0.946(2) 1.039(3) 0.9277(16) 0.020 Uiso 1 1 d . . . C23 C 0.8973(2) 0.9118(3) 0.86237(16) 0.0135(6) Uani 1 1 d . . . H23A H 0.984(2) 0.885(2) 0.8565(14) 0.016 Uiso 1 1 d . . . H23B H 0.8750(19) 0.963(2) 0.8282(15) 0.016 Uiso 1 1 d . . . C24 C 0.8372(2) 0.7360(3) 0.91638(15) 0.0121(6) Uani 1 1 d . . . H24A H 0.922(2) 0.702(2) 0.9114(16) 0.015 Uiso 1 1 d . . . H24B H 0.781(2) 0.668(2) 0.9164(15) 0.015 Uiso 1 1 d . . . C25 C 0.8236(2) 0.7981(3) 0.98010(16) 0.0160(7) Uani 1 1 d . . . H25 H 0.851(2) 0.747(2) 1.0148(16) 0.019 Uiso 1 1 d . . . C26 C 0.9113(2) 0.8973(3) 0.98177(15) 0.0167(7) Uani 1 1 d . . . H26A H 0.997(2) 0.872(3) 0.9788(16) 0.020 Uiso 1 1 d . . . H26B H 0.905(2) 0.935(3) 1.0281(17) 0.020 Uiso 1 1 d . . . C27 C 0.6963(3) 0.8422(3) 0.98664(17) 0.0176(7) Uani 1 1 d . . . H27A H 0.688(2) 0.878(2) 1.0280(18) 0.021 Uiso 1 1 d . . . H27B H 0.641(2) 0.777(2) 0.9901(14) 0.021 Uiso 1 1 d . . . C28 C 0.7543(2) 0.6616(2) 0.78177(16) 0.0099(6) Uani 1 1 d . . . H28 H 0.676(2) 0.661(2) 0.8022(14) 0.012 Uiso 1 1 d . . . C29 C 0.8130(2) 0.5543(3) 0.80150(14) 0.0113(6) Uani 1 1 d . . . C30 C 0.7463(2) 0.4670(2) 0.82571(15) 0.0107(6) Uani 1 1 d . . . H30 H 0.666(2) 0.477(2) 0.8298(13) 0.013 Uiso 1 1 d . . . C31 C 0.7964(2) 0.3637(2) 0.83708(17) 0.0135(6) Uani 1 1 d . . . H31 H 0.752(2) 0.313(2) 0.8516(15) 0.016 Uiso 1 1 d . . . C32 C 0.9157(2) 0.3496(2) 0.82393(15) 0.0130(6) Uani 1 1 d . . . C33 C 0.9851(2) 0.4348(3) 0.80129(17) 0.0172(7) Uani 1 1 d . . . H33 H 1.069(2) 0.423(2) 0.7932(16) 0.021 Uiso 1 1 d . . . C34 C 0.9337(2) 0.5362(3) 0.78974(15) 0.0133(6) Uani 1 1 d . . . H34 H 0.983(2) 0.590(2) 0.7769(12) 0.016 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0265(3) 0.0148(4) 0.0333(5) -0.0068(4) 0.0016(3) -0.0072(3) Cl2 0.0248(3) 0.0123(4) 0.0325(5) 0.0044(4) 0.0008(3) 0.0069(3) N1 0.0116(9) 0.0085(13) 0.0127(13) -0.0006(11) -0.0004(9) 0.0032(8) N2 0.0151(10) 0.0128(14) 0.0072(12) -0.0012(11) 0.0024(9) -0.0002(8) C1 0.0128(11) 0.0150(16) 0.0104(16) 0.0016(13) -0.0005(10) 0.0012(10) C2 0.0179(12) 0.0154(16) 0.0100(15) 0.0095(12) -0.0025(10) 0.0016(10) C3 0.0144(12) 0.0232(18) 0.0219(18) 0.0077(15) 0.0000(11) -0.0067(11) C4 0.0313(15) 0.0121(17) 0.0105(16) 0.0022(14) -0.0024(12) -0.0025(12) C5 0.0193(13) 0.0112(15) 0.0110(14) 0.0063(13) 0.0023(10) 0.0043(11) C6 0.0166(12) 0.0133(16) 0.0142(15) -0.0019(13) -0.0007(11) 0.0046(11) C7 0.0151(12) 0.0106(16) 0.0168(18) -0.0058(15) -0.0018(11) 0.0012(11) C8 0.0242(14) 0.0121(17) 0.0088(18) -0.0007(14) -0.0004(12) 0.0004(11) C9 0.0184(13) 0.0151(18) 0.0093(16) -0.0014(13) -0.0020(11) -0.0001(11) C10 0.0185(13) 0.024(2) 0.021(2) 0.0128(16) 0.0064(13) 0.0066(12) C11 0.0091(10) 0.0177(15) 0.0065(14) -0.0021(11) 0.0010(9) 0.0022(9) C12 0.0133(11) 0.0062(14) 0.0068(13) 0.0012(11) -0.0030(9) 0.0005(9) C13 0.0112(11) 0.0219(16) 0.0118(16) -0.0004(12) 0.0005(10) 0.0016(10) C14 0.0175(12) 0.0149(16) 0.0124(16) -0.0017(14) -0.0013(12) 0.0009(10) C15 0.0162(12) 0.0140(16) 0.0162(16) -0.0004(13) -0.0049(11) -0.0030(10) C16 0.0123(11) 0.0142(15) 0.0115(14) -0.0021(12) -0.0010(10) -0.0015(9) C17 0.0130(12) 0.0130(15) 0.0150(15) -0.0010(12) -0.0019(10) 0.0027(10) C18 0.0122(11) 0.0052(15) 0.0104(16) 0.0003(12) -0.0001(10) -0.0023(9) C19 0.0097(11) 0.0173(17) 0.0216(17) 0.0005(14) -0.0017(10) 0.0061(10) C20 0.0133(11) 0.0188(17) 0.0177(17) -0.0101(14) -0.0011(11) 0.0022(10) C21 0.0238(14) 0.0134(18) 0.022(2) -0.0078(15) -0.0030(12) 0.0033(12) C22 0.0184(13) 0.0133(16) 0.0176(17) 0.0028(14) -0.0063(11) -0.0056(11) C23 0.0178(12) 0.0119(15) 0.0108(15) 0.0014(12) -0.0002(10) -0.0031(10) C24 0.0156(11) 0.0112(16) 0.0094(16) -0.0043(14) -0.0019(11) -0.0009(10) C25 0.0212(13) 0.0164(18) 0.0105(18) 0.0020(15) -0.0027(12) -0.0063(11) C26 0.0176(13) 0.0184(18) 0.0139(17) -0.0047(14) -0.0030(11) -0.0035(11) C27 0.0237(14) 0.020(2) 0.0092(17) -0.0019(14) 0.0040(12) -0.0093(12) C28 0.0115(12) 0.0054(13) 0.0127(15) -0.0040(11) -0.0007(9) -0.0006(9) C29 0.0127(11) 0.0161(16) 0.0050(13) -0.0028(12) -0.0018(9) -0.0007(9) C30 0.0138(12) 0.0096(13) 0.0086(15) 0.0004(11) 0.0007(10) 0.0002(9) C31 0.0177(12) 0.0116(15) 0.0113(15) 0.0028(13) 0.0021(12) -0.0045(10) C32 0.0231(12) 0.0056(14) 0.0102(15) 0.0006(12) -0.0036(10) 0.0053(10) C33 0.0101(11) 0.0211(17) 0.0204(16) -0.0055(13) 0.0006(11) 0.0000(10) C34 0.0146(12) 0.0123(15) 0.0131(14) 0.0001(12) -0.0016(10) -0.0050(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 C15 1.735(3) . ? Cl2 C32 1.758(3) . ? N1 C11 1.464(4) . ? N1 C1 1.483(4) . ? N1 H1N 0.86(2) . ? N2 C28 1.477(4) . ? N2 C18 1.484(4) . ? N2 H2N 0.88(2) . ? C1 C2 1.515(4) . ? C1 C6 1.537(4) . ? C1 C7 1.539(4) . ? C2 C3 1.548(5) . ? C2 H2A 1.03(3) . ? C2 H2B 1.00(3) . ? C3 C10 1.520(5) . ? C3 C4 1.535(4) . ? C3 H3 0.99(3) . ? C4 C5 1.527(4) . ? C4 H4A 0.91(3) . ? C4 H4B 1.06(3) . ? C5 C9 1.541(5) . ? C5 C6 1.548(4) . ? C5 H5 0.92(3) . ? C6 H6A 1.05(2) . ? C6 H6B 0.98(3) . ? C7 C8 1.547(5) . ? C7 H7A 0.91(3) . ? C7 H7B 0.97(3) . ? C8 C9 1.519(4) . ? C8 C10 1.539(4) . ? C8 H8B 0.95(3) . ? C9 H9A 0.99(3) . ? C9 H9B 0.90(4) . ? C10 H10A 0.99(3) . ? C10 H10B 0.99(4) . ? C11 C12 1.521(4) . ? C11 C28 1.572(2) . ? C11 H1 1.01(3) . ? C12 C17 1.394(3) . ? C12 C13 1.399(4) . ? C13 C14 1.382(4) . ? C13 H13 1.01(3) . ? C14 C15 1.387(4) . ? C14 H14 1.06(3) . ? C15 C16 1.395(4) . ? C16 C17 1.397(4) . ? C16 H16 0.95(3) . ? C17 H17 1.00(3) . ? C18 C24 1.536(4) . ? C18 C23 1.543(4) . ? C18 C19 1.559(3) . ? C19 C20 1.525(5) . ? C19 H19A 0.96(3) . ? C19 H19B 0.99(3) . ? C20 C21 1.527(4) . ? C20 C27 1.540(5) . ? C20 H20 0.99(3) . ? C21 C22 1.541(4) . ? C21 H21A 1.05(4) . ? C21 H21B 0.93(4) . ? C22 C26 1.525(5) . ? C22 C23 1.532(5) . ? C22 H22 1.04(3) . ? C23 H23A 1.04(2) . ? C23 H23B 0.98(3) . ? C24 C25 1.531(5) . ? C24 H24A 1.05(3) . ? C24 H24B 1.04(3) . ? C25 C27 1.537(4) . ? C25 C26 1.556(4) . ? C25 H25 1.00(3) . ? C26 H26A 1.02(3) . ? C26 H26B 1.07(3) . ? C27 H27A 0.97(4) . ? C27 H27B 1.00(3) . ? C28 C29 1.515(4) . ? C28 H28 0.98(3) . ? C29 C30 1.391(4) . ? C29 C34 1.401(3) . ? C30 C31 1.392(4) . ? C30 H30 0.92(2) . ? C31 C32 1.384(3) . ? C31 H31 0.85(3) . ? C32 C33 1.377(4) . ? C33 C34 1.379(5) . ? C33 H33 0.97(3) . ? C34 H34 0.90(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 C11 N1 C1 118.9(2) . . ? C11 N1 H1N 108.7(15) . . ? C1 N1 H1N 111.9(15) . . ? C28 N2 C18 117.1(2) . . ? C28 N2 H2N 107.3(14) . . ? C18 N2 H2N 104.1(14) . . ? N1 C1 C2 108.8(2) . . ? N1 C1 C6 107.1(2) . . ? C2 C1 C6 108.7(2) . . ? N1 C1 C7 114.3(2) . . ? C2 C1 C7 109.4(2) . . ? C6 C1 C7 108.4(2) . . ? C1 C2 C3 110.4(2) . . ? C1 C2 H2A 109.9(16) . . ? C3 C2 H2A 102.2(19) . . ? C1 C2 H2B 107.3(14) . . ? C3 C2 H2B 109.2(17) . . ? H2A C2 H2B 118(2) . . ? C10 C3 C4 109.7(3) . . ? C10 C3 C2 109.4(3) . . ? C4 C3 C2 109.0(3) . . ? C10 C3 H3 109.9(17) . . ? C4 C3 H3 112.0(18) . . ? C2 C3 H3 106.8(18) . . ? C5 C4 C3 109.4(2) . . ? C5 C4 H4A 110.2(18) . . ? C3 C4 H4A 110.3(19) . . ? C5 C4 H4B 107.6(14) . . ? C3 C4 H4B 112.0(14) . . ? H4A C4 H4B 107(3) . . ? C4 C5 C9 110.1(3) . . ? C4 C5 C6 108.7(2) . . ? C9 C5 C6 108.9(3) . . ? C4 C5 H5 109.7(18) . . ? C9 C5 H5 110(2) . . ? C6 C5 H5 110(2) . . ? C1 C6 C5 110.7(2) . . ? C1 C6 H6A 109.9(17) . . ? C5 C6 H6A 109.2(17) . . ? C1 C6 H6B 110.3(15) . . ? C5 C6 H6B 111.7(17) . . ? H6A C6 H6B 105(2) . . ? C1 C7 C8 109.9(3) . . ? C1 C7 H7A 105(2) . . ? C8 C7 H7A 111(2) . . ? C1 C7 H7B 107(2) . . ? C8 C7 H7B 110.4(19) . . ? H7A C7 H7B 113(3) . . ? C9 C8 C10 109.5(3) . . ? C9 C8 C7 110.2(3) . . ? C10 C8 C7 108.6(2) . . ? C9 C8 H8B 111.7(17) . . ? C10 C8 H8B 106.8(15) . . ? C7 C8 H8B 109.9(18) . . ? C8 C9 C5 109.4(2) . . ? C8 C9 H9A 108.4(18) . . ? C5 C9 H9A 110.4(17) . . ? C8 C9 H9B 111.1(19) . . ? C5 C9 H9B 107(2) . . ? H9A C9 H9B 111(3) . . ? C3 C10 C8 110.0(2) . . ? C3 C10 H10A 107.1(16) . . ? C8 C10 H10A 112.0(16) . . ? C3 C10 H10B 106.8(18) . . ? C8 C10 H10B 109.6(17) . . ? H10A C10 H10B 111(3) . . ? N1 C11 C12 116.5(2) . . ? N1 C11 C28 108.2(3) . . ? C12 C11 C28 109.3(3) . . ? N1 C11 H1 105.3(16) . . ? C12 C11 H1 111.1(16) . . ? C28 C11 H1 106.0(17) . . ? C17 C12 C13 118.3(3) . . ? C17 C12 C11 120.6(2) . . ? C13 C12 C11 120.9(2) . . ? C14 C13 C12 121.3(2) . . ? C14 C13 H13 118.6(17) . . ? C12 C13 H13 120.0(17) . . ? C13 C14 C15 119.8(3) . . ? C13 C14 H14 121.1(14) . . ? C15 C14 H14 119.1(14) . . ? C14 C15 C16 120.2(3) . . ? C14 C15 Cl1 120.2(2) . . ? C16 C15 Cl1 119.6(2) . . ? C15 C16 C17 119.4(2) . . ? C15 C16 H16 116.6(17) . . ? C17 C16 H16 124.1(17) . . ? C12 C17 C16 121.0(3) . . ? C12 C17 H17 119.7(15) . . ? C16 C17 H17 119.0(15) . . ? N2 C18 C24 113.3(2) . . ? N2 C18 C23 106.9(2) . . ? C24 C18 C23 108.5(2) . . ? N2 C18 C19 112.0(2) . . ? C24 C18 C19 108.9(2) . . ? C23 C18 C19 107.0(2) . . ? C20 C19 C18 111.3(2) . . ? C20 C19 H19A 114.9(19) . . ? C18 C19 H19A 108.8(17) . . ? C20 C19 H19B 111.7(18) . . ? C18 C19 H19B 108.8(15) . . ? H19A C19 H19B 101(2) . . ? C19 C20 C21 109.7(3) . . ? C19 C20 C27 109.2(3) . . ? C21 C20 C27 109.2(3) . . ? C19 C20 H20 111.8(17) . . ? C21 C20 H20 108.7(17) . . ? C27 C20 H20 108.3(16) . . ? C20 C21 C22 109.5(2) . . ? C20 C21 H21A 110.9(17) . . ? C22 C21 H21A 106.2(15) . . ? C20 C21 H21B 105.7(17) . . ? C22 C21 H21B 112.3(17) . . ? H21A C21 H21B 112(3) . . ? C26 C22 C23 109.4(3) . . ? C26 C22 C21 108.7(3) . . ? C23 C22 C21 110.4(2) . . ? C26 C22 H22 107.4(17) . . ? C23 C22 H22 109.8(18) . . ? C21 C22 H22 111.0(16) . . ? C22 C23 C18 111.0(2) . . ? C22 C23 H23A 110.4(17) . . ? C18 C23 H23A 110.1(16) . . ? C22 C23 H23B 106.7(16) . . ? C18 C23 H23B 107.4(15) . . ? H23A C23 H23B 111(2) . . ? C25 C24 C18 110.5(2) . . ? C25 C24 H24A 111.6(18) . . ? C18 C24 H24A 109.7(18) . . ? C25 C24 H24B 109.2(18) . . ? C18 C24 H24B 111.3(17) . . ? H24A C24 H24B 104(2) . . ? C24 C25 C27 109.9(2) . . ? C24 C25 C26 109.5(2) . . ? C27 C25 C26 108.9(3) . . ? C24 C25 H25 107.0(18) . . ? C27 C25 H25 115.9(15) . . ? C26 C25 H25 105.4(16) . . ? C22 C26 C25 109.3(2) . . ? C22 C26 H26A 109.4(17) . . ? C25 C26 H26A 111.5(17) . . ? C22 C26 H26B 114.6(18) . . ? C25 C26 H26B 107.8(17) . . ? H26A C26 H26B 104(2) . . ? C25 C27 C20 109.5(2) . . ? C25 C27 H27A 109.2(17) . . ? C20 C27 H27A 111.8(18) . . ? C25 C27 H27B 108.2(15) . . ? C20 C27 H27B 115.1(15) . . ? H27A C27 H27B 103(2) . . ? N2 C28 C29 112.8(2) . . ? N2 C28 C11 107.4(3) . . ? C29 C28 C11 110.3(3) . . ? N2 C28 H28 115.3(17) . . ? C29 C28 H28 105.6(17) . . ? C11 C28 H28 105.3(17) . . ? C30 C29 C34 118.1(3) . . ? C30 C29 C28 120.9(2) . . ? C34 C29 C28 120.8(3) . . ? C29 C30 C31 121.6(2) . . ? C29 C30 H30 117.9(17) . . ? C31 C30 H30 120.1(17) . . ? C32 C31 C30 118.1(3) . . ? C32 C31 H31 124.1(17) . . ? C30 C31 H31 117.8(17) . . ? C33 C32 C31 121.9(3) . . ? C33 C32 Cl2 119.3(2) . . ? C31 C32 Cl2 118.8(2) . . ? C32 C33 C34 119.2(2) . . ? C32 C33 H33 120.0(18) . . ? C34 C33 H33 120.9(18) . . ? C33 C34 C29 121.1(3) . . ? C33 C34 H34 116.4(17) . . ? C29 C34 H34 122.3(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N N1 0.88(2) 2.36(2) 2.8589(19) 115.9(16) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.348 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.050 data_ma0504 _database_code_depnum_ccdc_archive 'CCDC 840705' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H42 Cl2 N2' _chemical_formula_sum 'C34 H42 Cl2 N2' _chemical_formula_weight 549.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4218(5) _cell_length_b 10.300(2) _cell_length_c 10.942(1) _cell_angle_alpha 84.03(2) _cell_angle_beta 82.99(1) _cell_angle_gamma 83.11(1) _cell_volume 710.22(16) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 294 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS, Bruker AXS, 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method ; \w-rotations with 2.00 \% and 380 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13053 _diffrn_reflns_av_R_equivalents 0.0809 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 26.36 _reflns_number_total 2889 _reflns_number_gt 2050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Duisenberg, 2003)' _computing_data_reduction 'EVALCCD (Duisenberg, 2003)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _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^)+(0.0508P)^2^+0.7014P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2889 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0864 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 -0.09541(12) 0.68468(7) 0.97141(6) 0.0281(2) Uani 1 1 d . . . N1 N 0.3529(3) 0.6097(2) 0.3864(2) 0.0171(5) Uani 1 1 d . . . H1 H 0.431(5) 0.571(3) 0.330(3) 0.021 Uiso 1 1 d . . . C1 C 0.3228(4) 0.7497(2) 0.3364(2) 0.0132(5) Uani 1 1 d . . . C2 C 0.3092(5) 0.7491(3) 0.1968(2) 0.0191(6) Uani 1 1 d . . . H2A H 0.445(5) 0.708(3) 0.159(3) 0.023 Uiso 1 1 d . . . H2B H 0.194(5) 0.695(3) 0.181(3) 0.023 Uiso 1 1 d . . . C3 C 0.2658(4) 0.8897(3) 0.1353(2) 0.0205(6) Uani 1 1 d . . . H3 H 0.263(5) 0.883(3) 0.048(3) 0.025 Uiso 1 1 d . . . C4 C 0.4466(4) 0.9674(3) 0.1537(2) 0.0212(6) Uani 1 1 d . . . H4A H 0.579(5) 0.922(3) 0.114(3) 0.025 Uiso 1 1 d . . . H4B H 0.423(4) 1.059(3) 0.111(3) 0.025 Uiso 1 1 d . . . C5 C 0.4607(4) 0.9725(3) 0.2915(2) 0.0188(6) Uani 1 1 d . . . H5 H 0.571(5) 1.019(3) 0.303(3) 0.023 Uiso 1 1 d . . . C6 C 0.5023(4) 0.8311(3) 0.3532(2) 0.0182(6) Uani 1 1 d . . . H6A H 0.507(4) 0.835(3) 0.445(3) 0.022 Uiso 1 1 d . . . H6B H 0.645(5) 0.788(3) 0.313(3) 0.022 Uiso 1 1 d . . . C7 C 0.1129(4) 0.8176(3) 0.3958(2) 0.0173(6) Uani 1 1 d . . . H7A H -0.003(5) 0.762(3) 0.385(3) 0.021 Uiso 1 1 d . . . H7B H 0.116(4) 0.819(3) 0.490(3) 0.021 Uiso 1 1 d . . . C8 C 0.0714(4) 0.9585(3) 0.3336(2) 0.0189(6) Uani 1 1 d . . . H8 H -0.054(5) 1.002(3) 0.370(3) 0.023 Uiso 1 1 d . . . C9 C 0.2518(4) 1.0370(3) 0.3507(3) 0.0210(6) Uani 1 1 d . . . H9A H 0.260(5) 1.047(3) 0.433(3) 0.025 Uiso 1 1 d . . . H9B H 0.226(5) 1.126(3) 0.309(3) 0.025 Uiso 1 1 d . . . C10 C 0.0569(4) 0.9528(3) 0.1968(3) 0.0210(6) Uani 1 1 d . . . H10A H -0.051(5) 0.905(3) 0.184(3) 0.025 Uiso 1 1 d . . . H10B H 0.025(5) 1.045(3) 0.152(3) 0.025 Uiso 1 1 d . . . C11 C 0.4631(4) 0.5748(3) 0.4964(2) 0.0211(6) Uani 1 1 d . . . H11 H 0.588(5) 0.623(3) 0.491(3) 0.025 Uiso 1 1 d . . . C12 C 0.3186(4) 0.6061(3) 0.6140(2) 0.0206(6) Uani 1 1 d . . . C13 C 0.1226(4) 0.5564(3) 0.6420(3) 0.0240(6) Uani 1 1 d . . . H13 H 0.067(5) 0.504(3) 0.583(3) 0.029 Uiso 1 1 d . . . C14 C -0.0048(5) 0.5784(3) 0.7522(3) 0.0229(6) Uani 1 1 d . . . H14 H -0.137(5) 0.547(3) 0.771(3) 0.028 Uiso 1 1 d . . . C15 C 0.0658(4) 0.6525(3) 0.8348(2) 0.0205(6) Uani 1 1 d . . . C16 C 0.2587(5) 0.7021(3) 0.8101(3) 0.0254(6) Uani 1 1 d . . . H16 H 0.302(5) 0.752(3) 0.868(3) 0.030 Uiso 1 1 d . . . C17 C 0.3832(5) 0.6791(3) 0.6998(3) 0.0241(6) Uani 1 1 d . . . H17 H 0.524(5) 0.714(3) 0.684(3) 0.029 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0330(4) 0.0276(4) 0.0217(4) -0.0025(3) 0.0029(3) -0.0013(3) N1 0.0208(12) 0.0129(11) 0.0187(11) -0.0029(9) -0.0063(9) -0.0004(9) C1 0.0124(13) 0.0130(12) 0.0141(12) -0.0010(10) -0.0022(10) -0.0002(10) C2 0.0225(15) 0.0182(14) 0.0165(13) -0.0024(10) -0.0031(11) -0.0009(11) C3 0.0255(15) 0.0239(15) 0.0126(13) -0.0008(11) -0.0039(11) -0.0044(12) C4 0.0194(15) 0.0262(15) 0.0166(13) 0.0024(11) 0.0004(11) -0.0032(12) C5 0.0171(14) 0.0169(14) 0.0240(14) -0.0013(11) -0.0044(11) -0.0066(11) C6 0.0161(14) 0.0175(14) 0.0211(14) -0.0015(11) -0.0035(11) -0.0013(11) C7 0.0136(13) 0.0187(14) 0.0192(13) -0.0015(11) 0.0001(10) -0.0019(11) C8 0.0125(13) 0.0190(14) 0.0240(14) -0.0026(11) -0.0007(11) 0.0027(11) C9 0.0228(15) 0.0190(15) 0.0214(14) -0.0021(11) -0.0021(11) -0.0038(11) C10 0.0173(14) 0.0195(15) 0.0276(15) 0.0003(11) -0.0076(11) -0.0041(11) C11 0.0253(15) 0.0156(14) 0.0245(14) 0.0004(11) -0.0119(12) -0.0039(11) C12 0.0228(15) 0.0172(14) 0.0223(14) 0.0004(11) -0.0080(11) -0.0006(11) C13 0.0248(15) 0.0266(16) 0.0231(14) -0.0052(12) -0.0102(12) -0.0022(12) C14 0.0211(15) 0.0196(15) 0.0281(15) 0.0004(11) -0.0061(12) -0.0009(12) C15 0.0250(15) 0.0157(14) 0.0197(13) -0.0021(10) -0.0031(11) 0.0035(11) C16 0.0271(16) 0.0264(16) 0.0252(15) -0.0093(12) -0.0064(12) -0.0039(12) C17 0.0211(15) 0.0231(15) 0.0295(15) -0.0046(12) -0.0066(12) -0.0027(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C15 1.749(3) . ? N1 C11 1.462(3) . ? N1 C1 1.487(3) . ? N1 H1 0.85(3) . ? C1 C2 1.541(3) . ? C1 C6 1.543(3) . ? C1 C7 1.544(3) . ? C2 C3 1.541(4) . ? C2 H2A 0.99(3) . ? C2 H2B 1.01(3) . ? C3 C10 1.529(4) . ? C3 C4 1.530(4) . ? C3 H3 0.96(3) . ? C4 C5 1.529(4) . ? C4 H4A 0.99(3) . ? C4 H4B 1.01(3) . ? C5 C9 1.524(4) . ? C5 C6 1.548(4) . ? C5 H5 0.93(3) . ? C6 H6A 1.01(3) . ? C6 H6B 1.04(3) . ? C7 C8 1.545(4) . ? C7 H7A 1.01(3) . ? C7 H7B 1.03(3) . ? C8 C10 1.519(4) . ? C8 C9 1.530(4) . ? C8 H8 0.93(3) . ? C9 H9A 0.93(3) . ? C9 H9B 0.98(3) . ? C10 H10A 0.93(3) . ? C10 H10B 1.03(3) . ? C11 C12 1.531(4) . ? C11 C11 1.553(5) 2_666 ? C11 H11 0.99(3) . ? C12 C17 1.391(4) . ? C12 C13 1.403(4) . ? C13 C14 1.394(4) . ? C13 H13 1.01(3) . ? C14 C15 1.390(4) . ? C14 H14 0.94(3) . ? C15 C16 1.382(4) . ? C16 C17 1.389(4) . ? C16 H16 0.94(3) . ? C17 H17 1.00(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 C11 N1 C1 119.2(2) . . ? C11 N1 H1 104(2) . . ? C1 N1 H1 105(2) . . ? N1 C1 C2 106.27(19) . . ? N1 C1 C6 114.8(2) . . ? C2 C1 C6 108.3(2) . . ? N1 C1 C7 110.3(2) . . ? C2 C1 C7 108.5(2) . . ? C6 C1 C7 108.5(2) . . ? C1 C2 C3 111.2(2) . . ? C1 C2 H2A 108.1(17) . . ? C3 C2 H2A 109.5(17) . . ? C1 C2 H2B 111.1(16) . . ? C3 C2 H2B 109.1(17) . . ? H2A C2 H2B 108(2) . . ? C10 C3 C4 110.2(2) . . ? C10 C3 C2 108.6(2) . . ? C4 C3 C2 108.5(2) . . ? C10 C3 H3 112.5(18) . . ? C4 C3 H3 109.6(17) . . ? C2 C3 H3 107.3(17) . . ? C5 C4 C3 110.2(2) . . ? C5 C4 H4A 110.0(17) . . ? C3 C4 H4A 107.6(17) . . ? C5 C4 H4B 111.0(16) . . ? C3 C4 H4B 109.1(16) . . ? H4A C4 H4B 109(2) . . ? C9 C5 C4 108.9(2) . . ? C9 C5 C6 109.2(2) . . ? C4 C5 C6 109.3(2) . . ? C9 C5 H5 110.4(17) . . ? C4 C5 H5 110.2(18) . . ? C6 C5 H5 108.7(18) . . ? C1 C6 C5 110.4(2) . . ? C1 C6 H6A 108.3(16) . . ? C5 C6 H6A 108.8(16) . . ? C1 C6 H6B 109.8(15) . . ? C5 C6 H6B 108.9(16) . . ? H6A C6 H6B 111(2) . . ? C1 C7 C8 110.0(2) . . ? C1 C7 H7A 107.6(16) . . ? C8 C7 H7A 111.5(17) . . ? C1 C7 H7B 110.5(16) . . ? C8 C7 H7B 110.4(16) . . ? H7A C7 H7B 107(2) . . ? C10 C8 C9 110.0(2) . . ? C10 C8 C7 109.4(2) . . ? C9 C8 C7 109.3(2) . . ? C10 C8 H8 109.4(18) . . ? C9 C8 H8 107.6(17) . . ? C7 C8 H8 111.1(18) . . ? C5 C9 C8 110.2(2) . . ? C5 C9 H9A 110.5(19) . . ? C8 C9 H9A 112.1(18) . . ? C5 C9 H9B 108.0(17) . . ? C8 C9 H9B 108.9(17) . . ? H9A C9 H9B 107(2) . . ? C8 C10 C3 109.8(2) . . ? C8 C10 H10A 111.5(18) . . ? C3 C10 H10A 109.1(18) . . ? C8 C10 H10B 112.1(16) . . ? C3 C10 H10B 108.1(16) . . ? H10A C10 H10B 106(2) . . ? N1 C11 C12 111.2(2) . . ? N1 C11 C11 108.3(3) . 2_666 ? C12 C11 C11 109.3(3) . 2_666 ? N1 C11 H11 110.5(17) . . ? C12 C11 H11 108.5(16) . . ? C11 C11 H11 109.0(18) 2_666 . ? C17 C12 C13 117.9(3) . . ? C17 C12 C11 120.8(2) . . ? C13 C12 C11 121.3(2) . . ? C14 C13 C12 121.6(3) . . ? C14 C13 H13 117.0(17) . . ? C12 C13 H13 121.3(17) . . ? C15 C14 C13 118.4(3) . . ? C15 C14 H14 119.6(18) . . ? C13 C14 H14 122.0(18) . . ? C16 C15 C14 121.2(3) . . ? C16 C15 Cl1 119.8(2) . . ? C14 C15 Cl1 118.9(2) . . ? C15 C16 C17 119.4(3) . . ? C15 C16 H16 119.3(19) . . ? C17 C16 H16 121.3(19) . . ? C16 C17 C12 121.4(3) . . ? C16 C17 H17 118.3(17) . . ? C12 C17 H17 120.3(17) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.557 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.063 #===END OF ALL DATA