data_dr82 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H27 Cl N2 O2' _chemical_formula_weight 350.88 _chemical_absolute_configuration 'ab' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.8906(6) _cell_length_b 5.7704(3) _cell_length_c 13.5908(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.185(4) _cell_angle_gamma 90.00 _cell_volume 895.55(8) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4736 _cell_measurement_theta_min 3.39 _cell_measurement_theta_max 60.65 _exptl_crystal_description plate _exptl_crystal_colour 'colorless ' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 1.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6914 _exptl_absorpt_correction_T_max 0.9612 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MWPC area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18976 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 62.33 _reflns_number_total 2697 _reflns_number_gt 2288 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1348P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 2697 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1691 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.08622(8) 0.39010(17) 0.10516(8) 0.0244(3) Uani 1 1 d . . . O1 O 0.7835(2) 1.1137(6) 0.2631(2) 0.0245(7) Uani 1 1 d . . . O2 O 0.4584(3) 0.6170(6) 0.1218(2) 0.0294(8) Uani 1 1 d . . . N1 N 0.4798(3) 0.9843(7) 0.1908(3) 0.0258(9) Uani 1 1 d . . . N2 N 0.1720(3) 0.8844(8) 0.0753(2) 0.0213(8) Uani 1 1 d . . . H2A H 0.1310 0.7490 0.0746 0.026 Uiso 1 1 calc R . . H2B H 0.1209 1.0071 0.0676 0.026 Uiso 1 1 calc R . . C1 C 0.7274(4) 0.9157(10) 0.6087(3) 0.0302(12) Uani 1 1 d . . . H1 H 0.7597 0.8374 0.6718 0.036 Uiso 1 1 calc R . . C2 C 0.6363(4) 0.8200(9) 0.5345(4) 0.0331(13) Uani 1 1 d . . . H2 H 0.6053 0.6751 0.5474 0.040 Uiso 1 1 calc R . . C3 C 0.5885(4) 0.9287(9) 0.4413(3) 0.0264(12) Uani 1 1 d . . . H3 H 0.5267 0.8567 0.3908 0.032 Uiso 1 1 calc R . . C4 C 0.6321(4) 1.1485(9) 0.4215(3) 0.0236(10) Uani 1 1 d . . . C5 C 0.5813(4) 1.2821(9) 0.3236(3) 0.0249(11) Uani 1 1 d . . . H5A H 0.6282 1.4246 0.3258 0.030 Uiso 1 1 calc R . . H5B H 0.5008 1.3306 0.3218 0.030 Uiso 1 1 calc R . . C6 C 0.5759(4) 1.1523(8) 0.2232(3) 0.0222(10) Uani 1 1 d . . . H6 H 0.5681 1.2690 0.1673 0.027 Uiso 1 1 calc R . . C7 C 0.6794(4) 1.0041(9) 0.2274(4) 0.0243(11) Uani 1 1 d . . . C8 C 0.8959(4) 0.9860(9) 0.2931(3) 0.0242(10) Uani 1 1 d . . . C9 C 0.8902(4) 0.8023(9) 0.3724(4) 0.0300(11) Uani 1 1 d . . . H9A H 0.8727 0.8767 0.4312 0.045 Uiso 1 1 calc R . . H9B H 0.9657 0.7223 0.3951 0.045 Uiso 1 1 calc R . . H9C H 0.8286 0.6900 0.3416 0.045 Uiso 1 1 calc R . . C10 C 0.9215(4) 0.8854(11) 0.1986(3) 0.0251(10) Uani 1 1 d . . . H10A H 0.8591 0.7773 0.1651 0.038 Uiso 1 1 calc R . . H10B H 0.9965 0.8030 0.2186 0.038 Uiso 1 1 calc R . . H10C H 0.9256 1.0109 0.1511 0.038 Uiso 1 1 calc R . . C11 C 0.9827(4) 1.1756(10) 0.3406(4) 0.0325(12) Uani 1 1 d . . . H11A H 0.9810 1.2964 0.2896 0.049 Uiso 1 1 calc R . . H11B H 1.0617 1.1096 0.3638 0.049 Uiso 1 1 calc R . . H11C H 0.9615 1.2430 0.3992 0.049 Uiso 1 1 calc R . . C12 C 0.3608(4) 1.0670(8) 0.1441(3) 0.0211(10) Uani 1 1 d . . . H12 H 0.3531 1.2276 0.1691 0.025 Uiso 1 1 calc R . . C13 C 0.3239(4) 1.0679(9) 0.0252(4) 0.0288(11) Uani 1 1 d . . . H13A H 0.2924 1.2216 -0.0011 0.035 Uiso 1 1 calc R . . H13B H 0.3919 1.0325 -0.0008 0.035 Uiso 1 1 calc R . . C14 C 0.2307(4) 0.8838(10) -0.0085(3) 0.0267(10) Uani 1 1 d . . . H14A H 0.1749 0.9240 -0.0752 0.032 Uiso 1 1 calc R . . H14B H 0.2660 0.7308 -0.0143 0.032 Uiso 1 1 calc R . . C15 C 0.2679(3) 0.9064(10) 0.1731(3) 0.0221(9) Uani 1 1 d . . . H15A H 0.3020 0.7531 0.1972 0.027 Uiso 1 1 calc R . . H15B H 0.2386 0.9782 0.2274 0.027 Uiso 1 1 calc R . . C16 C 0.5204(4) 0.7774(8) 0.1659(3) 0.0238(10) Uani 1 1 d . . . C17 C 0.6503(4) 0.7866(9) 0.1983(4) 0.0238(10) Uani 1 1 d . . . H17 H 0.7025 0.6619 0.1982 0.029 Uiso 1 1 calc R . . C18 C 0.7718(4) 1.1301(10) 0.5898(4) 0.0319(12) Uani 1 1 d . . . H18 H 0.8341 1.1995 0.6408 0.038 Uiso 1 1 calc R . . C19 C 0.7254(4) 1.2434(9) 0.4963(4) 0.0270(11) Uani 1 1 d . . . H19 H 0.7580 1.3870 0.4837 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0233(6) 0.0172(6) 0.0326(6) 0.0006(5) 0.0076(4) -0.0002(5) O1 0.0197(17) 0.0226(19) 0.0309(17) -0.0025(14) 0.0065(13) -0.0002(14) O2 0.0318(18) 0.0218(19) 0.0335(18) -0.0008(15) 0.0075(14) 0.0019(15) N1 0.018(2) 0.019(2) 0.035(2) -0.0057(17) -0.0010(17) -0.0001(16) N2 0.0144(17) 0.0208(19) 0.0279(19) -0.0005(19) 0.0046(14) -0.0029(17) C1 0.026(3) 0.040(3) 0.025(2) 0.010(2) 0.0074(19) 0.003(2) C2 0.031(3) 0.033(3) 0.040(3) 0.001(2) 0.018(2) -0.002(2) C3 0.021(2) 0.031(3) 0.028(3) -0.002(2) 0.0087(19) 0.001(2) C4 0.019(2) 0.027(3) 0.025(2) -0.003(2) 0.0075(18) 0.0043(19) C5 0.027(3) 0.021(3) 0.027(3) 0.002(2) 0.008(2) 0.002(2) C6 0.018(2) 0.019(3) 0.030(2) 0.003(2) 0.0085(18) -0.0008(19) C7 0.024(3) 0.027(3) 0.026(2) 0.002(2) 0.014(2) 0.000(2) C8 0.017(2) 0.028(3) 0.025(2) -0.0011(19) 0.0003(19) 0.0062(19) C9 0.024(3) 0.034(3) 0.030(3) 0.004(2) 0.005(2) 0.002(2) C10 0.017(2) 0.033(3) 0.025(2) -0.007(2) 0.0053(17) -0.001(2) C11 0.025(3) 0.034(3) 0.035(3) -0.005(2) 0.003(2) 0.007(2) C12 0.018(2) 0.017(2) 0.026(2) 0.0005(18) 0.0029(18) -0.0045(17) C13 0.029(3) 0.029(3) 0.030(3) 0.007(2) 0.013(2) 0.000(2) C14 0.027(2) 0.028(3) 0.024(2) -0.001(2) 0.0034(18) 0.001(2) C15 0.014(2) 0.030(3) 0.023(2) 0.000(2) 0.0057(16) 0.001(2) C16 0.025(3) 0.014(2) 0.024(2) -0.0002(19) -0.0067(19) -0.003(2) C17 0.025(3) 0.016(2) 0.034(3) -0.003(2) 0.014(2) 0.001(2) C18 0.024(3) 0.046(3) 0.024(3) -0.003(2) 0.0035(19) -0.003(2) C19 0.020(2) 0.027(3) 0.036(3) -0.001(2) 0.010(2) -0.005(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 O1 C7 1.354(6) . ? O1 C8 1.481(5) . ? O2 C16 1.230(5) . ? N1 C16 1.365(6) . ? N1 C12 1.461(6) . ? N1 C6 1.469(6) . ? N2 C14 1.492(5) . ? N2 C15 1.497(5) . ? N2 H2A 0.9200 . ? N2 H2B 0.9200 . ? C1 C2 1.373(7) . ? C1 C18 1.397(7) . ? C1 H1 0.9500 . ? C2 C3 1.385(7) . ? C2 H2 0.9500 . ? C3 C4 1.425(7) . ? C3 H3 0.9500 . ? C4 C19 1.390(6) . ? C4 C5 1.510(6) . ? C5 C6 1.543(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.486(7) . ? C6 H6 1.0000 . ? C7 C17 1.333(7) . ? C8 C10 1.515(6) . ? C8 C11 1.519(7) . ? C8 C9 1.526(7) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.551(6) . ? C12 C15 1.574(6) . ? C12 H12 1.0000 . ? C13 C14 1.511(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.485(6) . ? C17 H17 0.9500 . ? C18 C19 1.398(7) . ? C18 H18 0.9500 . ? C19 H19 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 C7 O1 C8 122.1(4) . . ? C16 N1 C12 123.0(4) . . ? C16 N1 C6 110.6(4) . . ? C12 N1 C6 119.5(4) . . ? C14 N2 C15 106.0(3) . . ? C14 N2 H2A 110.5 . . ? C15 N2 H2A 110.5 . . ? C14 N2 H2B 110.5 . . ? C15 N2 H2B 110.5 . . ? H2A N2 H2B 108.7 . . ? C2 C1 C18 118.8(5) . . ? C2 C1 H1 120.6 . . ? C18 C1 H1 120.6 . . ? C1 C2 C3 121.9(5) . . ? C1 C2 H2 119.1 . . ? C3 C2 H2 119.1 . . ? C2 C3 C4 119.8(4) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C19 C4 C3 118.1(4) . . ? C19 C4 C5 119.0(4) . . ? C3 C4 C5 122.9(4) . . ? C4 C5 C6 116.1(4) . . ? C4 C5 H5A 108.3 . . ? C6 C5 H5A 108.3 . . ? C4 C5 H5B 108.3 . . ? C6 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? N1 C6 C7 101.4(4) . . ? N1 C6 C5 115.0(4) . . ? C7 C6 C5 114.5(4) . . ? N1 C6 H6 108.5 . . ? C7 C6 H6 108.5 . . ? C5 C6 H6 108.5 . . ? C17 C7 O1 133.0(5) . . ? C17 C7 C6 112.8(4) . . ? O1 C7 C6 114.2(4) . . ? O1 C8 C10 109.7(4) . . ? O1 C8 C11 102.3(4) . . ? C10 C8 C11 111.3(4) . . ? O1 C8 C9 109.0(4) . . ? C10 C8 C9 113.0(4) . . ? C11 C8 C9 111.0(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 C13 114.4(4) . . ? N1 C12 C15 111.2(4) . . ? C13 C12 C15 104.4(3) . . ? N1 C12 H12 108.9 . . ? C13 C12 H12 108.9 . . ? C15 C12 H12 108.9 . . ? C14 C13 C12 106.5(4) . . ? C14 C13 H13A 110.4 . . ? C12 C13 H13A 110.4 . . ? C14 C13 H13B 110.4 . . ? C12 C13 H13B 110.4 . . ? H13A C13 H13B 108.6 . . ? N2 C14 C13 103.1(4) . . ? N2 C14 H14A 111.1 . . ? C13 C14 H14A 111.1 . . ? N2 C14 H14B 111.1 . . ? C13 C14 H14B 111.1 . . ? H14A C14 H14B 109.1 . . ? N2 C15 C12 103.9(3) . . ? N2 C15 H15A 111.0 . . ? C12 C15 H15A 111.0 . . ? N2 C15 H15B 111.0 . . ? C12 C15 H15B 111.0 . . ? H15A C15 H15B 109.0 . . ? O2 C16 N1 125.0(4) . . ? O2 C16 C17 127.1(4) . . ? N1 C16 C17 107.8(4) . . ? C7 C17 C16 106.5(4) . . ? C7 C17 H17 126.8 . . ? C16 C17 H17 126.8 . . ? C1 C18 C19 120.5(5) . . ? C1 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C4 C19 C18 120.8(5) . . ? C4 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? 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 C18 C1 C2 C3 0.8(7) . . . . ? C1 C2 C3 C4 -1.5(7) . . . . ? C2 C3 C4 C19 2.3(6) . . . . ? C2 C3 C4 C5 -177.4(4) . . . . ? C19 C4 C5 C6 125.2(5) . . . . ? C3 C4 C5 C6 -55.1(6) . . . . ? C16 N1 C6 C7 -7.7(5) . . . . ? C12 N1 C6 C7 -159.5(4) . . . . ? C16 N1 C6 C5 -131.8(4) . . . . ? C12 N1 C6 C5 76.4(5) . . . . ? C4 C5 C6 N1 77.8(5) . . . . ? C4 C5 C6 C7 -39.1(6) . . . . ? C8 O1 C7 C17 -10.1(7) . . . . ? C8 O1 C7 C6 167.2(4) . . . . ? N1 C6 C7 C17 2.4(5) . . . . ? C5 C6 C7 C17 126.8(5) . . . . ? N1 C6 C7 O1 -175.5(4) . . . . ? C5 C6 C7 O1 -51.1(5) . . . . ? C7 O1 C8 C10 69.3(5) . . . . ? C7 O1 C8 C11 -172.5(4) . . . . ? C7 O1 C8 C9 -54.9(5) . . . . ? C16 N1 C12 C13 -52.7(6) . . . . ? C6 N1 C12 C13 95.5(5) . . . . ? C16 N1 C12 C15 65.3(5) . . . . ? C6 N1 C12 C15 -146.6(4) . . . . ? N1 C12 C13 C14 111.8(4) . . . . ? C15 C12 C13 C14 -9.9(5) . . . . ? C15 N2 C14 C13 -41.2(5) . . . . ? C12 C13 C14 N2 30.8(5) . . . . ? C14 N2 C15 C12 34.7(5) . . . . ? N1 C12 C15 N2 -138.5(4) . . . . ? C13 C12 C15 N2 -14.7(5) . . . . ? C12 N1 C16 O2 -17.7(7) . . . . ? C6 N1 C16 O2 -168.3(4) . . . . ? C12 N1 C16 C17 160.5(4) . . . . ? C6 N1 C16 C17 9.9(5) . . . . ? O1 C7 C17 C16 -179.5(5) . . . . ? C6 C7 C17 C16 3.2(5) . . . . ? O2 C16 C17 C7 170.1(5) . . . . ? N1 C16 C17 C7 -8.1(5) . . . . ? C2 C1 C18 C19 -0.9(7) . . . . ? C3 C4 C19 C18 -2.4(7) . . . . ? C5 C4 C19 C18 177.3(4) . . . . ? C1 C18 C19 C4 1.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 62.33 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.949 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.087