data_global _journal_coden_cambridge 0177 loop_ _publ_author_name 'Kenner C. Rice' 'Arthur E. Jacobson' _publ_contact_author_name 'Dr Kenner C Rice' _publ_contact_author_address ; Laboratory of Medicinal Chemistry NIDDK Building 8 Room B1-23 Bethesda Maryland 20892 UNITED STATES OF AMERICA ; _publ_contact_author_email AEJ@HELIX.NIH.GOV _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthesis of ac-(1R,4aR,9aR)-1,3,4,9a-tetrahydro-2-methyl-2H-4,4a-propanobenzofuro[2. 3-c]pyridin-6-ol.An Unusual Double Rearrangement Leading to the ortho- and para-f Oxide-Bridged Phenylmorphan Isomers ; data_rice44 _database_code_depnum_ccdc_archive 'CCDC 220253' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H20 N O2, Br' _chemical_formula_sum 'C15 H20 Br N O2' _chemical_formula_weight 326.23 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' O O 0.0106 0.0060 '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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.841(2) _cell_length_b 11.998(3) _cell_length_c 12.157(3) _cell_angle_alpha 103.14(2) _cell_angle_beta 97.91(2) _cell_angle_gamma 103.65(2) _cell_volume 1465.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 2.803 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.616 _exptl_absorpt_correction_T_max 0.870 _exptl_absorpt_process_details 'Bruker XPREP v5.1 (Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_detector_area_resol_mean ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5233 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.05 _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.942 _reflns_number_total 4895 _reflns_number_gt 2908 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'Bruker Shelxtl v6.10 (Bruker, 2000)' _computing_molecular_graphics 'Bruker Shelxtl v6.10 (Bruker, 2000)' _computing_publication_material 'Bruker Shelxtl v6.10 (Bruker, 2000)' _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^)+(0.0595P)^2^+9.1372P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4895 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1402 _refine_ls_R_factor_gt 0.0754 _refine_ls_wR_factor_ref 0.2017 _refine_ls_wR_factor_gt 0.1702 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.828 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.117 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 -0.38571(11) 0.49481(9) 0.26180(9) 0.0551(4) Uani 1 1 d . . . C1 C 0.3751(10) 0.1962(8) 0.1260(8) 0.045(2) Uani 1 1 d . . . H1A H 0.4301 0.1983 0.1979 0.054 Uiso 1 1 calc R . . N2 N 0.4582(7) 0.2636(7) 0.0570(6) 0.0395(19) Uani 1 1 d . . . C2A C 0.5567(10) 0.2021(9) 0.0197(9) 0.054(3) Uani 1 1 d . . . H2AA H 0.6067 0.2454 -0.0242 0.080 Uiso 1 1 calc R . . H2AB H 0.5134 0.1227 -0.0270 0.080 Uiso 1 1 calc R . . H2AC H 0.6131 0.1990 0.0864 0.080 Uiso 1 1 calc R . . C3 C 0.3887(10) 0.2917(9) -0.0451(8) 0.048(3) Uani 1 1 d . . . H3A H 0.3604 0.2204 -0.1093 0.057 Uiso 1 1 calc R . . H3B H 0.4495 0.3516 -0.0676 0.057 Uiso 1 1 calc R . . C4 C 0.2710(10) 0.3368(9) -0.0236(8) 0.047(3) Uani 1 1 d . . . H4A H 0.2178 0.3303 -0.0970 0.056 Uiso 1 1 calc R . . H4B H 0.3003 0.4202 0.0191 0.056 Uiso 1 1 calc R . . C4A C 0.1890(9) 0.2658(8) 0.0444(7) 0.037(2) Uani 1 1 d . . . C4B C 0.0933(9) 0.3175(8) 0.1041(7) 0.036(2) Uani 1 1 d . . . C5 C -0.0014(9) 0.3675(8) 0.0693(8) 0.042(2) Uani 1 1 d . . . H5A H -0.0097 0.3833 -0.0024 0.050 Uiso 1 1 calc R . . C6 C -0.0852(9) 0.3944(8) 0.1422(8) 0.039(2) Uani 1 1 d . . . O6 O -0.1760(7) 0.4472(7) 0.1037(7) 0.067(2) Uani 1 1 d . . . H6 H -0.2202 0.4596 0.1523 0.080 Uiso 1 1 calc R . . C7 C -0.0748(10) 0.3686(10) 0.2477(9) 0.057(3) Uani 1 1 d . . . H7A H -0.1333 0.3840 0.2944 0.069 Uiso 1 1 calc R . . C8 C 0.0231(11) 0.3194(10) 0.2851(9) 0.059(3) Uani 1 1 d . . . H8A H 0.0320 0.3036 0.3568 0.071 Uiso 1 1 calc R . . C9 C 0.1048(10) 0.2957(8) 0.2128(8) 0.045(2) Uani 1 1 d . . . O9 O 0.2067(7) 0.2448(6) 0.2352(5) 0.0518(19) Uani 1 1 d . . . C9A C 0.2850(9) 0.2735(8) 0.1534(7) 0.038(2) Uani 1 1 d . . . H9AA H 0.3380 0.3563 0.1845 0.045 Uiso 1 1 calc R . . C10 C 0.1164(11) 0.1362(9) -0.0219(9) 0.057(3) Uani 1 1 d . . . H10A H 0.0539 0.1051 0.0213 0.069 Uiso 1 1 calc R . . H10B H 0.0684 0.1360 -0.0954 0.069 Uiso 1 1 calc R . . C11 C 0.2024(10) 0.0517(9) -0.0445(10) 0.056(3) Uani 1 1 d . . . H11A H 0.1486 -0.0301 -0.0698 0.067 Uiso 1 1 calc R . . H11B H 0.2473 0.0672 -0.1055 0.067 Uiso 1 1 calc R . . C12 C 0.3012(11) 0.0686(9) 0.0644(10) 0.058(3) Uani 1 1 d . . . H12A H 0.2564 0.0339 0.1176 0.070 Uiso 1 1 calc R . . H12B H 0.3630 0.0247 0.0440 0.070 Uiso 1 1 calc R . . Br2 Br -0.39869(11) 0.06184(10) 0.26788(8) 0.0535(4) Uani 1 1 d . . . C1' C 0.4102(12) -0.1763(10) 0.4083(9) 0.059(3) Uani 1 1 d . . . H1'A H 0.4847 -0.1053 0.4318 0.070 Uiso 1 1 calc R . . N2' N 0.4102(9) -0.2477(8) 0.4990(7) 0.051(2) Uani 1 1 d . . . C2A' C 0.5269(12) -0.2905(11) 0.5151(10) 0.076(4) Uani 1 1 d . . . H2AD H 0.5216 -0.3349 0.5716 0.113 Uiso 1 1 calc R . . H2AE H 0.6027 -0.2236 0.5410 0.113 Uiso 1 1 calc R . . H2AF H 0.5321 -0.3408 0.4432 0.113 Uiso 1 1 calc R . . C3' C 0.2894(12) -0.3496(11) 0.4785(10) 0.067(3) Uani 1 1 d . . . H3'A H 0.2917 -0.3805 0.5456 0.080 Uiso 1 1 calc R . . H3'B H 0.2914 -0.4128 0.4134 0.080 Uiso 1 1 calc R . . C4' C 0.1589(13) -0.3180(11) 0.4544(10) 0.072(4) Uani 1 1 d . . . H4'A H 0.0886 -0.3909 0.4242 0.087 Uiso 1 1 calc R . . H4'B H 0.1431 -0.2740 0.5260 0.087 Uiso 1 1 calc R . . C4A' C 0.1610(11) -0.2451(9) 0.3698(9) 0.052(3) Uani 1 1 d . . . C4B' C 0.0672(11) -0.1711(10) 0.3641(8) 0.053(3) Uani 1 1 d . . . C5' C -0.0717(12) -0.2026(10) 0.3598(9) 0.068(3) Uani 1 1 d . . . H5'A H -0.1132 -0.2727 0.2959 0.082 Uiso 1 1 calc R . . H5'B H -0.0879 -0.2230 0.4303 0.082 Uiso 1 1 calc R . . C6' C -0.1293(11) -0.1095(11) 0.3465(9) 0.059(3) Uani 1 1 d . . . O6' O -0.2599(8) -0.1358(8) 0.3465(8) 0.084(3) Uani 1 1 d . . . H6' H -0.2990 -0.1291 0.2867 0.101 Uiso 1 1 calc R . . C7' C -0.0632(11) -0.0031(11) 0.3353(9) 0.061(3) Uani 1 1 d . . . H7'A H -0.1067 0.0532 0.3254 0.073 Uiso 1 1 calc R . . C8' C 0.0708(13) 0.0226(11) 0.3385(10) 0.069(3) Uani 1 1 d . . . H8'A H 0.1186 0.0955 0.3325 0.083 Uiso 1 1 calc R . . C9' C 0.1266(11) -0.0661(10) 0.3509(9) 0.057(3) Uani 1 1 d . . . O9' O 0.2635(7) -0.0521(6) 0.3577(6) 0.060(2) Uani 1 1 d . . . C9A' C 0.2842(11) -0.1410(9) 0.4137(9) 0.055(3) Uani 1 1 d . . . H9AB H 0.2864 -0.1076 0.4956 0.066 Uiso 1 1 calc R . . C10' C 0.1636(13) -0.3110(11) 0.2440(9) 0.069(3) Uani 1 1 d . . . H10C H 0.0953 -0.3246 0.1828 0.083 Uiso 1 1 calc R . . C11' C 0.2827(13) -0.3513(10) 0.2272(9) 0.066(3) Uani 1 1 d . . . H11C H 0.2831 -0.4172 0.2607 0.079 Uiso 1 1 calc R . . H11D H 0.2802 -0.3793 0.1453 0.079 Uiso 1 1 calc R . . C12' C 0.4052(13) -0.2521(11) 0.2821(10) 0.070(3) Uani 1 1 d . . . H12C H 0.4170 -0.1985 0.2330 0.084 Uiso 1 1 calc R . . H12D H 0.4779 -0.2863 0.2843 0.084 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0497(7) 0.0519(6) 0.0608(7) 0.0006(5) 0.0200(6) 0.0173(5) C1 0.054(7) 0.055(6) 0.051(6) 0.028(5) 0.032(5) 0.037(5) N2 0.034(4) 0.057(5) 0.044(4) 0.022(4) 0.019(4) 0.028(4) C2A 0.056(7) 0.069(7) 0.056(6) 0.018(6) 0.033(6) 0.041(6) C3 0.056(7) 0.052(6) 0.050(6) 0.023(5) 0.026(5) 0.024(5) C4 0.058(7) 0.055(6) 0.046(6) 0.026(5) 0.024(5) 0.029(5) C4A 0.049(6) 0.037(5) 0.039(5) 0.015(4) 0.018(5) 0.027(5) C4B 0.039(5) 0.038(5) 0.034(5) 0.010(4) 0.012(4) 0.015(4) C5 0.050(6) 0.044(5) 0.038(5) 0.013(4) 0.012(5) 0.020(5) C6 0.030(5) 0.039(5) 0.051(6) 0.011(5) 0.010(5) 0.014(4) O6 0.059(5) 0.096(6) 0.081(5) 0.046(5) 0.040(4) 0.055(5) C7 0.055(7) 0.075(8) 0.064(7) 0.031(6) 0.038(6) 0.032(6) C8 0.072(8) 0.081(8) 0.059(7) 0.040(6) 0.046(6) 0.046(7) C9 0.053(7) 0.040(5) 0.056(6) 0.024(5) 0.022(5) 0.025(5) O9 0.066(5) 0.074(5) 0.049(4) 0.037(4) 0.036(4) 0.049(4) C9A 0.039(6) 0.046(5) 0.039(5) 0.017(4) 0.018(4) 0.019(5) C10 0.059(7) 0.048(6) 0.061(7) -0.004(5) 0.022(6) 0.020(5) C11 0.040(6) 0.040(6) 0.078(8) -0.007(5) 0.018(6) 0.012(5) C12 0.065(8) 0.053(7) 0.083(8) 0.032(6) 0.045(7) 0.037(6) Br2 0.0618(8) 0.0692(7) 0.0391(6) 0.0103(5) 0.0119(5) 0.0395(6) C1' 0.084(9) 0.063(7) 0.052(6) 0.025(6) 0.041(6) 0.037(6) N2' 0.061(6) 0.062(6) 0.042(5) 0.018(4) 0.011(4) 0.036(5) C2A' 0.077(9) 0.100(10) 0.075(8) 0.025(7) 0.018(7) 0.070(8) C3' 0.090(10) 0.074(8) 0.052(7) 0.019(6) 0.027(7) 0.043(8) C4' 0.106(11) 0.077(8) 0.055(7) 0.020(6) 0.045(7) 0.046(8) C4A' 0.055(7) 0.048(6) 0.053(6) 0.010(5) 0.012(5) 0.017(6) C4B' 0.062(8) 0.058(7) 0.038(6) 0.006(5) 0.003(5) 0.029(6) C5' 0.074(9) 0.073(8) 0.037(6) -0.011(6) -0.007(6) 0.018(7) C6' 0.047(7) 0.079(8) 0.053(7) 0.009(6) -0.002(6) 0.034(7) O6' 0.060(6) 0.099(7) 0.095(7) 0.027(5) 0.011(5) 0.026(5) C7' 0.046(7) 0.070(8) 0.055(7) 0.009(6) 0.007(6) 0.004(6) C8' 0.082(10) 0.063(8) 0.066(8) 0.020(6) 0.016(7) 0.024(7) C9' 0.055(7) 0.065(8) 0.048(6) 0.009(6) 0.010(6) 0.018(6) O9' 0.059(5) 0.061(5) 0.070(5) 0.023(4) 0.023(4) 0.022(4) C9A' 0.084(9) 0.065(7) 0.045(6) 0.029(5) 0.031(6) 0.049(7) C10' 0.082(9) 0.087(9) 0.034(6) -0.005(6) 0.002(6) 0.043(7) C11' 0.100(10) 0.055(7) 0.040(6) 0.002(5) 0.022(6) 0.021(7) C12' 0.088(10) 0.080(8) 0.058(7) 0.021(6) 0.032(7) 0.042(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C12 1.510(14) . ? C1 C9A 1.518(11) . ? C1 N2 1.530(11) . ? C1 H1A 0.9800 . ? N2 C2A 1.497(11) . ? N2 C3 1.509(11) . ? C2A H2AA 0.9600 . ? C2A H2AB 0.9600 . ? C2A H2AC 0.9600 . ? C3 C4 1.529(12) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C4A 1.538(12) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4A C4B 1.515(12) . ? C4A C9A 1.539(12) . ? C4A C10 1.537(13) . ? C4B C5 1.371(12) . ? C4B C9 1.399(12) . ? C5 C6 1.395(12) . ? C5 H5A 0.9300 . ? C6 O6 1.376(10) . ? C6 C7 1.382(13) . ? O6 H6 0.8200 . ? C7 C8 1.402(14) . ? C7 H7A 0.9300 . ? C8 C9 1.363(13) . ? C8 H8A 0.9300 . ? C9 O9 1.406(11) . ? O9 C9A 1.442(10) . ? C9A H9AA 0.9800 . ? C10 C11 1.538(13) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.526(15) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C1' C9A' 1.528(14) . ? C1' N2' 1.543(12) . ? C1' C12' 1.582(14) . ? C1' H1'A 0.9800 . ? N2' C2A' 1.479(12) . ? N2' C3' 1.513(15) . ? C2A' H2AD 0.9600 . ? C2A' H2AE 0.9600 . ? C2A' H2AF 0.9600 . ? C3' C4' 1.555(16) . ? C3' H3'A 0.9700 . ? C3' H3'B 0.9700 . ? C4' C4A' 1.493(14) . ? C4' H4'A 0.9700 . ? C4' H4'B 0.9700 . ? C4A' C4B' 1.504(14) . ? C4A' C9A' 1.531(15) . ? C4A' C10' 1.562(14) . ? C4B' C9' 1.329(15) . ? C4B' C5' 1.454(15) . ? C5' C6' 1.430(15) . ? C5' H5'A 0.9700 . ? C5' H5'B 0.9700 . ? C6' C7' 1.355(15) . ? C6' O6' 1.376(13) . ? O6' H6' 0.8200 . ? C7' C8' 1.404(16) . ? C7' H7'A 0.9300 . ? C8' C9' 1.369(15) . ? C8' H8'A 0.9300 . ? C9' O9' 1.442(13) . ? O9' C9A' 1.433(11) . ? C9A' H9AB 0.9800 . ? C10' C11' 1.505(16) . ? C10' H10C 0.9300 . ? C11' C12' 1.508(16) . ? C11' H11C 0.9700 . ? C11' H11D 0.9700 . ? C12' H12C 0.9700 . ? C12' H12D 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 C1 C9A 111.9(9) . . ? C12 C1 N2 115.8(8) . . ? C9A C1 N2 101.4(7) . . ? C12 C1 H1A 109.1 . . ? C9A C1 H1A 109.1 . . ? N2 C1 H1A 109.1 . . ? C2A N2 C3 109.2(7) . . ? C2A N2 C1 111.0(7) . . ? C3 N2 C1 117.5(7) . . ? N2 C2A H2AA 109.5 . . ? N2 C2A H2AB 109.5 . . ? H2AA C2A H2AB 109.5 . . ? N2 C2A H2AC 109.5 . . ? H2AA C2A H2AC 109.5 . . ? H2AB C2A H2AC 109.5 . . ? N2 C3 C4 114.5(7) . . ? N2 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? N2 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C4A 111.8(7) . . ? C3 C4 H4A 109.3 . . ? C4A C4 H4A 109.3 . . ? C3 C4 H4B 109.3 . . ? C4A C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C4B C4A C9A 97.6(7) . . ? C4B C4A C10 106.5(8) . . ? C9A C4A C10 112.0(7) . . ? C4B C4A C4 119.5(7) . . ? C9A C4A C4 104.8(8) . . ? C10 C4A C4 115.0(8) . . ? C5 C4B C9 119.2(8) . . ? C5 C4B C4A 133.5(8) . . ? C9 C4B C4A 107.0(7) . . ? C4B C5 C6 119.4(8) . . ? C4B C5 H5A 120.3 . . ? C6 C5 H5A 120.3 . . ? O6 C6 C7 122.9(9) . . ? O6 C6 C5 116.7(8) . . ? C7 C6 C5 120.4(8) . . ? C6 O6 H6 109.5 . . ? C6 C7 C8 120.6(9) . . ? C6 C7 H7A 119.7 . . ? C8 C7 H7A 119.7 . . ? C9 C8 C7 117.7(9) . . ? C9 C8 H8A 121.2 . . ? C7 C8 H8A 121.2 . . ? C8 C9 C4B 122.6(9) . . ? C8 C9 O9 125.4(9) . . ? C4B C9 O9 112.0(8) . . ? C9 O9 C9A 102.8(6) . . ? O9 C9A C1 115.4(7) . . ? O9 C9A C4A 105.7(7) . . ? C1 C9A C4A 111.4(7) . . ? O9 C9A H9AA 108.0 . . ? C1 C9A H9AA 108.0 . . ? C4A C9A H9AA 108.0 . . ? C11 C10 C4A 115.3(9) . . ? C11 C10 H10A 108.5 . . ? C4A C10 H10A 108.5 . . ? C11 C10 H10B 108.5 . . ? C4A C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C12 C11 C10 110.7(8) . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C1 C12 C11 115.3(8) . . ? C1 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? C1 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C9A' C1' N2' 101.1(8) . . ? C9A' C1' C12' 110.0(9) . . ? N2' C1' C12' 113.8(8) . . ? C9A' C1' H1'A 110.5 . . ? N2' C1' H1'A 110.5 . . ? C12' C1' H1'A 110.5 . . ? C2A' N2' C3' 110.1(9) . . ? C2A' N2' C1' 112.9(8) . . ? C3' N2' C1' 114.4(8) . . ? N2' C2A' H2AD 109.5 . . ? N2' C2A' H2AE 109.5 . . ? H2AD C2A' H2AE 109.5 . . ? N2' C2A' H2AF 109.5 . . ? H2AD C2A' H2AF 109.5 . . ? H2AE C2A' H2AF 109.5 . . ? N2' C3' C4' 115.5(9) . . ? N2' C3' H3'A 108.4 . . ? C4' C3' H3'A 108.4 . . ? N2' C3' H3'B 108.4 . . ? C4' C3' H3'B 108.4 . . ? H3'A C3' H3'B 107.5 . . ? C4A' C4' C3' 111.1(10) . . ? C4A' C4' H4'A 109.4 . . ? C3' C4' H4'A 109.4 . . ? C4A' C4' H4'B 109.4 . . ? C3' C4' H4'B 109.4 . . ? H4'A C4' H4'B 108.0 . . ? C4' C4A' C4B' 119.6(9) . . ? C4' C4A' C9A' 107.0(9) . . ? C4B' C4A' C9A' 96.6(8) . . ? C4' C4A' C10' 115.6(9) . . ? C4B' C4A' C10' 108.3(8) . . ? C9A' C4A' C10' 107.4(9) . . ? C9' C4B' C5' 119.8(10) . . ? C9' C4B' C4A' 109.8(10) . . ? C5' C4B' C4A' 130.1(10) . . ? C6' C5' C4B' 113.5(11) . . ? C6' C5' H5'A 108.9 . . ? C4B' C5' H5'A 108.9 . . ? C6' C5' H5'B 108.9 . . ? C4B' C5' H5'B 108.9 . . ? H5'A C5' H5'B 107.7 . . ? C7' C6' O6' 121.5(10) . . ? C7' C6' C5' 124.0(12) . . ? O6' C6' C5' 114.5(11) . . ? C6' O6' H6' 109.5 . . ? C6' C7' C8' 120.4(12) . . ? C6' C7' H7'A 119.8 . . ? C8' C7' H7'A 119.8 . . ? C9' C8' C7' 116.0(12) . . ? C9' C8' H8'A 122.0 . . ? C7' C8' H8'A 122.0 . . ? C4B' C9' C8' 126.3(12) . . ? C4B' C9' O9' 111.3(10) . . ? C8' C9' O9' 122.4(11) . . ? C9A' O9' C9' 101.9(8) . . ? O9' C9A' C1' 117.3(8) . . ? O9' C9A' C4A' 106.0(8) . . ? C1' C9A' C4A' 114.6(9) . . ? O9' C9A' H9AB 106.0 . . ? C1' C9A' H9AB 106.0 . . ? C4A' C9A' H9AB 106.0 . . ? C11' C10' C4A' 116.3(9) . . ? C11' C10' H10C 121.8 . . ? C4A' C10' H10C 121.8 . . ? C12' C11' C10' 111.7(9) . . ? C12' C11' H11C 109.3 . . ? C10' C11' H11C 109.3 . . ? C12' C11' H11D 109.3 . . ? C10' C11' H11D 109.3 . . ? H11C C11' H11D 107.9 . . ? C11' C12' C1' 115.8(10) . . ? C11' C12' H12C 108.3 . . ? C1' C12' H12C 108.3 . . ? C11' C12' H12D 108.3 . . ? C1' C12' H12D 108.3 . . ? H12C C12' H12D 107.4 . . ? 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 C12 C1 N2 C2A -58.7(11) . . . . ? C9A C1 N2 C2A -180.0(8) . . . . ? C12 C1 N2 C3 68.1(10) . . . . ? C9A C1 N2 C3 -53.2(10) . . . . ? C2A N2 C3 C4 170.8(9) . . . . ? C1 N2 C3 C4 43.2(11) . . . . ? N2 C3 C4 C4A -42.2(12) . . . . ? C3 C4 C4A C4B 162.2(8) . . . . ? C3 C4 C4A C9A 54.4(10) . . . . ? C3 C4 C4A C10 -69.1(11) . . . . ? C9A C4A C4B C5 160.7(11) . . . . ? C10 C4A C4B C5 -83.5(13) . . . . ? C4 C4A C4B C5 49.0(15) . . . . ? C9A C4A C4B C9 -25.6(9) . . . . ? C10 C4A C4B C9 90.2(9) . . . . ? C4 C4A C4B C9 -137.3(9) . . . . ? C9 C4B C5 C6 -0.8(14) . . . . ? C4A C4B C5 C6 172.3(9) . . . . ? C4B C5 C6 O6 178.4(9) . . . . ? C4B C5 C6 C7 -1.4(15) . . . . ? O6 C6 C7 C8 -177.2(10) . . . . ? C5 C6 C7 C8 2.5(16) . . . . ? C6 C7 C8 C9 -1.5(17) . . . . ? C7 C8 C9 C4B -0.7(17) . . . . ? C7 C8 C9 O9 -178.9(10) . . . . ? C5 C4B C9 C8 1.8(15) . . . . ? C4A C4B C9 C8 -173.0(10) . . . . ? C5 C4B C9 O9 -179.8(9) . . . . ? C4A C4B C9 O9 5.5(11) . . . . ? C8 C9 O9 C9A -162.5(10) . . . . ? C4B C9 O9 C9A 19.1(10) . . . . ? C9 O9 C9A C1 -159.4(8) . . . . ? C9 O9 C9A C4A -35.8(9) . . . . ? C12 C1 C9A O9 65.8(11) . . . . ? N2 C1 C9A O9 -170.2(7) . . . . ? C12 C1 C9A C4A -54.7(10) . . . . ? N2 C1 C9A C4A 69.4(9) . . . . ? C4B C4A C9A O9 37.6(8) . . . . ? C10 C4A C9A O9 -73.7(9) . . . . ? C4 C4A C9A O9 160.9(7) . . . . ? C4B C4A C9A C1 163.6(7) . . . . ? C10 C4A C9A C1 52.3(10) . . . . ? C4 C4A C9A C1 -73.1(9) . . . . ? C4B C4A C10 C11 -154.6(9) . . . . ? C9A C4A C10 C11 -49.0(12) . . . . ? C4 C4A C10 C11 70.5(12) . . . . ? C4A C10 C11 C12 45.8(13) . . . . ? C9A C1 C12 C11 54.1(11) . . . . ? N2 C1 C12 C11 -61.4(11) . . . . ? C10 C11 C12 C1 -48.4(12) . . . . ? C9A' C1' N2' C2A' -178.0(9) . . . . ? C12' C1' N2' C2A' 64.1(13) . . . . ? C9A' C1' N2' C3' 55.1(10) . . . . ? C12' C1' N2' C3' -62.8(12) . . . . ? C2A' N2' C3' C4' -177.3(9) . . . . ? C1' N2' C3' C4' -48.9(11) . . . . ? N2' C3' C4' C4A' 45.4(13) . . . . ? C3' C4' C4A' C4B' -159.4(10) . . . . ? C3' C4' C4A' C9A' -51.2(12) . . . . ? C3' C4' C4A' C10' 68.4(13) . . . . ? C4' C4A' C4B' C9' 139.1(11) . . . . ? C9A' C4A' C4B' C9' 25.3(10) . . . . ? C10' C4A' C4B' C9' -85.5(11) . . . . ? C4' C4A' C4B' C5' -47.4(16) . . . . ? C9A' C4A' C4B' C5' -161.2(10) . . . . ? C10' C4A' C4B' C5' 88.0(13) . . . . ? C9' C4B' C5' C6' -2.8(14) . . . . ? C4A' C4B' C5' C6' -175.8(10) . . . . ? C4B' C5' C6' C7' 2.0(16) . . . . ? C4B' C5' C6' O6' -177.7(9) . . . . ? O6' C6' C7' C8' 178.4(10) . . . . ? C5' C6' C7' C8' -1.3(17) . . . . ? C6' C7' C8' C9' 1.3(16) . . . . ? C5' C4B' C9' C8' 3.4(17) . . . . ? C4A' C4B' C9' C8' 177.6(10) . . . . ? C5' C4B' C9' O9' -179.9(9) . . . . ? C4A' C4B' C9' O9' -5.6(12) . . . . ? C7' C8' C9' C4B' -2.5(17) . . . . ? C7' C8' C9' O9' -178.9(9) . . . . ? C4B' C9' O9' C9A' -18.6(11) . . . . ? C8' C9' O9' C9A' 158.3(10) . . . . ? C9' O9' C9A' C1' 164.3(9) . . . . ? C9' O9' C9A' C4A' 34.9(9) . . . . ? N2' C1' C9A' O9' 167.4(9) . . . . ? C12' C1' C9A' O9' -72.0(12) . . . . ? N2' C1' C9A' C4A' -67.3(10) . . . . ? C12' C1' C9A' C4A' 53.3(11) . . . . ? C4' C4A' C9A' O9' -160.3(8) . . . . ? C4B' C4A' C9A' O9' -36.6(9) . . . . ? C10' C4A' C9A' O9' 75.0(9) . . . . ? C4' C4A' C9A' C1' 68.7(10) . . . . ? C4B' C4A' C9A' C1' -167.6(8) . . . . ? C10' C4A' C9A' C1' -56.0(11) . . . . ? C4' C4A' C10' C11' -65.0(15) . . . . ? C4B' C4A' C10' C11' 157.7(10) . . . . ? C9A' C4A' C10' C11' 54.3(12) . . . . ? C4A' C10' C11' C12' -50.0(14) . . . . ? C10' C11' C12' C1' 45.4(13) . . . . ? C9A' C1' C12' C11' -47.1(13) . . . . ? N2' C1' C12' C11' 65.5(13) . . . . ? #========================================================================== # END OF CIF #========================================================================== #========================================================================== data_rice45 _database_code_depnum_ccdc_archive 'CCDC 220254' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H25 Cl N O2, H2 O, Cl' _chemical_formula_sum 'C17 H27 Cl2 N O3' _chemical_formula_weight 364.30 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.5210(10) _cell_length_b 8.1870(10) _cell_length_c 17.336(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.720(10) _cell_angle_gamma 90.00 _cell_volume 924.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.365 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_T_max 0.787 _exptl_absorpt_process_details 'Bruker XPREP v5.1 (Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_detector_area_resol_mean ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 1989 _diffrn_reflns_av_R_equivalents 0.0128 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.05 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 1767 _reflns_number_gt 1674 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'Bruker Shelxtl v6.10 (Bruker, 2000)' _computing_molecular_graphics 'Bruker Shelxtl v6.10 (Bruker, 2000)' _computing_publication_material 'Bruker Shelxtl v6.10 (Bruker, 2000)' _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^)+(0.0551P)^2^+0.1304P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.19(8) _refine_ls_number_reflns 1767 _refine_ls_number_parameters 214 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.229 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.043 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 0.18602(10) 0.47958(10) 0.82480(4) 0.0443(2) Uani 1 1 d . . . N1 N -0.0053(4) 0.3014(3) 0.61525(14) 0.0402(6) Uani 1 1 d . . . H1 H -0.1024 0.3757 0.5997 0.044 Uiso 1 1 calc R . . C2 C -0.0941(5) 0.1320(5) 0.60359(18) 0.0515(8) Uani 1 1 d . . . H2A H 0.0147 0.0516 0.6009 0.057 Uiso 1 1 calc R . . H2B H -0.1791 0.1269 0.5562 0.057 Uiso 1 1 calc R . . C3 C -0.2220(5) 0.1002(4) 0.67323(18) 0.0455(7) Uani 1 1 d . . . H3A H -0.1898 -0.0062 0.6952 0.050 Uiso 1 1 calc R . . H3B H -0.3672 0.1034 0.6583 0.050 Uiso 1 1 calc R . . C4 C -0.1669(4) 0.2386(4) 0.73358(15) 0.0343(6) Uani 1 1 d . . . C5 C -0.3405(4) 0.3659(4) 0.72792(17) 0.0386(6) Uani 1 1 d . . . H5A H -0.3829 0.3799 0.6739 0.042 Uiso 1 1 calc R . . H5B H -0.4572 0.3231 0.7541 0.042 Uiso 1 1 calc R . . C6 C -0.2857(5) 0.5336(4) 0.76201(19) 0.0436(7) Uani 1 1 d . . . H6A H -0.4027 0.6062 0.7552 0.048 Uiso 1 1 calc R . . H6B H -0.2527 0.5229 0.8169 0.048 Uiso 1 1 calc R . . C7 C -0.1031(5) 0.6057(4) 0.72241(18) 0.0436(7) Uani 1 1 d . . . H7A H -0.1421 0.6280 0.6688 0.048 Uiso 1 1 calc R . . H7B H -0.0647 0.7084 0.7469 0.048 Uiso 1 1 calc R . . C8 C 0.0794(4) 0.4916(4) 0.72635(14) 0.0368(6) Uani 1 1 d . . . H8 H 0.1846 0.5351 0.6934 0.040 Uiso 1 1 calc R . . C9 C 0.0309(4) 0.3157(4) 0.70172(15) 0.0334(6) Uani 1 1 d . . . H9 H 0.1483 0.2467 0.7175 0.037 Uiso 1 1 calc R . . C10 C -0.1292(4) 0.1654(4) 0.81492(16) 0.0348(6) Uani 1 1 d . . . C11 C 0.0258(4) 0.0506(4) 0.83081(17) 0.0401(7) Uani 1 1 d . . . C12 C 0.0547(4) -0.0171(5) 0.90357(17) 0.0491(7) Uani 1 1 d . . . H12 H 0.1585 -0.0935 0.9129 0.054 Uiso 1 1 calc R . . C13 C -0.0691(5) 0.0277(5) 0.96280(18) 0.0490(8) Uani 1 1 d . . . H13 H -0.0468 -0.0164 1.0119 0.054 Uiso 1 1 calc R . . C14 C -0.2257(4) 0.1383(4) 0.94820(16) 0.0388(6) Uani 1 1 d . . . C15 C -0.2553(4) 0.2059(3) 0.87485(16) 0.0361(6) Uani 1 1 d . . . H15 H -0.3617 0.2800 0.8656 0.040 Uiso 1 1 calc R . . O16 O 0.1433(3) 0.0055(3) 0.77007(12) 0.0528(6) Uani 1 1 d . . . C17 C 0.3280(5) -0.0817(5) 0.7864(2) 0.0541(8) Uani 1 1 d . . . H17A H 0.3930 -0.1046 0.7390 0.065 Uiso 1 1 calc R . . H17B H 0.2978 -0.1824 0.8118 0.065 Uiso 1 1 calc R . . H17C H 0.4184 -0.0171 0.8194 0.065 Uiso 1 1 calc R . . O18 O -0.3449(3) 0.1730(3) 1.00942(12) 0.0514(6) Uani 1 1 d . . . C19 C -0.5232(6) 0.2701(6) 0.9956(3) 0.0626(10) Uani 1 1 d . . . H19A H -0.5913 0.2846 1.0430 0.075 Uiso 1 1 calc R . . H19B H -0.6142 0.2166 0.9585 0.075 Uiso 1 1 calc R . . H19C H -0.4845 0.3747 0.9759 0.075 Uiso 1 1 calc R . . C20 C 0.1808(5) 0.3281(5) 0.56980(19) 0.0569(9) Uani 1 1 d . . . H20A H 0.1447 0.3170 0.5157 0.068 Uiso 1 1 calc R . . H20B H 0.2835 0.2487 0.5847 0.068 Uiso 1 1 calc R . . H20C H 0.2337 0.4359 0.5798 0.068 Uiso 1 1 calc R . . Cl2 Cl -0.40917(17) 0.24306(15) 0.40932(6) 0.0747(3) Uani 1 1 d . . . O1S O -0.2790(4) 0.4905(5) 0.53447(16) 0.0677(7) Uani 1 1 d . . . H1S H -0.374(7) 0.559(6) 0.551(3) 0.081 Uiso 1 1 d . . . H2S H -0.339(7) 0.431(7) 0.498(3) 0.081 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 0.0453(4) 0.0511(4) 0.0360(3) -0.0042(4) -0.0039(3) -0.0051(4) N1 0.0466(13) 0.0423(14) 0.0315(12) -0.0017(10) 0.0019(10) 0.0005(12) C2 0.066(2) 0.0448(19) 0.0436(17) -0.0102(15) 0.0002(14) -0.0060(17) C3 0.0536(17) 0.0382(17) 0.0441(16) -0.0043(14) -0.0039(14) -0.0077(15) C4 0.0360(13) 0.0321(14) 0.0344(13) 0.0012(12) -0.0016(10) -0.0012(12) C5 0.0335(13) 0.0422(16) 0.0397(15) 0.0052(14) -0.0034(11) -0.0003(13) C6 0.0436(15) 0.0360(16) 0.0510(17) 0.0027(13) 0.0011(13) 0.0095(13) C7 0.0545(17) 0.0321(16) 0.0437(16) 0.0033(13) -0.0036(13) -0.0007(14) C8 0.0393(13) 0.0389(15) 0.0320(12) 0.0019(14) 0.0004(10) -0.0078(14) C9 0.0349(13) 0.0368(15) 0.0283(13) -0.0011(11) 0.0001(10) 0.0023(12) C10 0.0368(13) 0.0297(14) 0.0377(14) 0.0027(12) -0.0001(11) -0.0035(12) C11 0.0424(15) 0.0338(15) 0.0445(15) 0.0032(13) 0.0058(12) 0.0026(13) C12 0.0477(15) 0.0495(17) 0.0500(16) 0.0121(18) 0.0024(12) 0.0133(17) C13 0.0509(16) 0.056(2) 0.0400(15) 0.0146(14) -0.0008(13) 0.0041(15) C14 0.0419(14) 0.0379(16) 0.0367(14) 0.0016(13) 0.0042(12) -0.0075(13) C15 0.0354(13) 0.0300(15) 0.0430(15) 0.0022(12) 0.0012(11) -0.0021(11) O16 0.0613(12) 0.0487(15) 0.0496(11) 0.0075(11) 0.0133(10) 0.0226(12) C17 0.0460(17) 0.0481(19) 0.069(2) -0.0046(17) 0.0107(15) 0.0062(15) O18 0.0538(12) 0.0598(14) 0.0413(11) 0.0019(11) 0.0107(9) 0.0022(12) C19 0.059(2) 0.074(3) 0.0559(19) -0.003(2) 0.0160(16) 0.011(2) C20 0.065(2) 0.065(2) 0.0423(17) -0.0024(17) 0.0177(15) -0.0014(19) Cl2 0.0977(7) 0.0695(6) 0.0559(5) -0.0033(5) -0.0070(5) -0.0007(6) O1S 0.0737(16) 0.0709(19) 0.0565(14) 0.0008(16) -0.0165(12) 0.0035(17) _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 C8 1.815(3) . ? N1 C20 1.494(4) . ? N1 C9 1.511(4) . ? N1 C2 1.513(4) . ? N1 H1 0.9100 . ? C2 C3 1.522(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.572(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.538(4) . ? C4 C10 1.541(4) . ? C4 C9 1.560(4) . ? C5 C6 1.530(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.522(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.512(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.531(4) . ? C8 H8 0.9800 . ? C9 H9 0.9800 . ? C10 C15 1.395(4) . ? C10 C11 1.398(4) . ? C11 O16 1.382(3) . ? C11 C12 1.383(4) . ? C12 C13 1.385(4) . ? C12 H12 0.9300 . ? C13 C14 1.379(4) . ? C13 H13 0.9300 . ? C14 O18 1.375(3) . ? C14 C15 1.392(4) . ? C15 H15 0.9300 . ? O16 C17 1.417(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? O18 C19 1.419(5) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? O1S H1S 0.90(5) . ? O1S H2S 0.88(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 N1 C9 114.8(2) . . ? C20 N1 C2 112.3(3) . . ? C9 N1 C2 104.1(2) . . ? C20 N1 H1 108.5 . . ? C9 N1 H1 108.5 . . ? C2 N1 H1 108.5 . . ? N1 C2 C3 105.7(3) . . ? N1 C2 H2A 110.6 . . ? C3 C2 H2A 110.6 . . ? N1 C2 H2B 110.6 . . ? C3 C2 H2B 110.6 . . ? H2A C2 H2B 108.7 . . ? C2 C3 C4 106.8(3) . . ? C2 C3 H3A 110.4 . . ? C4 C3 H3A 110.4 . . ? C2 C3 H3B 110.4 . . ? C4 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? C5 C4 C10 114.0(2) . . ? C5 C4 C9 108.8(2) . . ? C10 C4 C9 112.5(2) . . ? C5 C4 C3 107.5(2) . . ? C10 C4 C3 110.5(2) . . ? C9 C4 C3 102.9(2) . . ? C6 C5 C4 115.2(2) . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5B 108.5 . . ? C4 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C7 C6 C5 110.3(3) . . ? C7 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? C7 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C6 111.8(3) . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C7 C8 C9 114.6(2) . . ? C7 C8 Cl1 110.0(2) . . ? C9 C8 Cl1 106.0(2) . . ? C7 C8 H8 108.7 . . ? C9 C8 H8 108.7 . . ? Cl1 C8 H8 108.7 . . ? N1 C9 C8 111.7(2) . . ? N1 C9 C4 103.1(2) . . ? C8 C9 C4 116.4(2) . . ? N1 C9 H9 108.4 . . ? C8 C9 H9 108.4 . . ? C4 C9 H9 108.4 . . ? C15 C10 C11 117.3(2) . . ? C15 C10 C4 121.0(2) . . ? C11 C10 C4 121.6(2) . . ? O16 C11 C12 122.1(3) . . ? O16 C11 C10 116.8(2) . . ? C12 C11 C10 121.0(3) . . ? C11 C12 C13 120.7(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 119.4(3) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? O18 C14 C13 115.8(3) . . ? O18 C14 C15 124.3(3) . . ? C13 C14 C15 119.9(3) . . ? C14 C15 C10 121.6(3) . . ? C14 C15 H15 119.2 . . ? C10 C15 H15 119.2 . . ? C11 O16 C17 118.6(2) . . ? O16 C17 H17A 109.5 . . ? O16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 O18 C19 118.3(3) . . ? O18 C19 H19A 109.5 . . ? O18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N1 C20 H20A 109.5 . . ? N1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? H1S O1S H2S 107(4) . . ? 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 C20 N1 C2 C3 158.7(3) . . . . ? C9 N1 C2 C3 33.9(3) . . . . ? N1 C2 C3 C4 -11.9(3) . . . . ? C2 C3 C4 C5 101.1(3) . . . . ? C2 C3 C4 C10 -133.9(3) . . . . ? C2 C3 C4 C9 -13.6(3) . . . . ? C10 C4 C5 C6 75.9(3) . . . . ? C9 C4 C5 C6 -50.5(3) . . . . ? C3 C4 C5 C6 -161.3(2) . . . . ? C4 C5 C6 C7 58.3(3) . . . . ? C5 C6 C7 C8 -55.2(3) . . . . ? C6 C7 C8 C9 49.4(3) . . . . ? C6 C7 C8 Cl1 -70.0(3) . . . . ? C20 N1 C9 C8 68.6(3) . . . . ? C2 N1 C9 C8 -168.3(2) . . . . ? C20 N1 C9 C4 -165.6(3) . . . . ? C2 N1 C9 C4 -42.5(3) . . . . ? C7 C8 C9 N1 73.7(3) . . . . ? Cl1 C8 C9 N1 -164.76(17) . . . . ? C7 C8 C9 C4 -44.4(3) . . . . ? Cl1 C8 C9 C4 77.1(2) . . . . ? C5 C4 C9 N1 -79.8(3) . . . . ? C10 C4 C9 N1 152.9(2) . . . . ? C3 C4 C9 N1 34.1(3) . . . . ? C5 C4 C9 C8 42.9(3) . . . . ? C10 C4 C9 C8 -84.4(3) . . . . ? C3 C4 C9 C8 156.8(2) . . . . ? C5 C4 C10 C15 4.4(4) . . . . ? C9 C4 C10 C15 128.8(3) . . . . ? C3 C4 C10 C15 -116.9(3) . . . . ? C5 C4 C10 C11 -178.6(3) . . . . ? C9 C4 C10 C11 -54.1(4) . . . . ? C3 C4 C10 C11 60.2(3) . . . . ? C15 C10 C11 O16 177.0(3) . . . . ? C4 C10 C11 O16 -0.2(4) . . . . ? C15 C10 C11 C12 -1.2(5) . . . . ? C4 C10 C11 C12 -178.4(3) . . . . ? O16 C11 C12 C13 -178.4(3) . . . . ? C10 C11 C12 C13 -0.2(5) . . . . ? C11 C12 C13 C14 1.5(5) . . . . ? C12 C13 C14 O18 178.3(3) . . . . ? C12 C13 C14 C15 -1.2(5) . . . . ? O18 C14 C15 C10 -179.8(3) . . . . ? C13 C14 C15 C10 -0.3(4) . . . . ? C11 C10 C15 C14 1.5(4) . . . . ? C4 C10 C15 C14 178.7(3) . . . . ? C12 C11 O16 C17 -15.3(5) . . . . ? C10 C11 O16 C17 166.5(3) . . . . ? C13 C14 O18 C19 -172.4(3) . . . . ? C15 C14 O18 C19 7.1(5) . . . . ? data_rice112 _database_code_depnum_ccdc_archive 'CCDC 220255' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H20 N O2, Cl' _chemical_formula_sum 'C15 H20 Cl N O2' _chemical_formula_weight 281.77 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' O O 0.0106 0.0060 '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 'P 21 21 21' 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 7.2507(11) _cell_length_b 12.939(2) _cell_length_c 15.788(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1481.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 5.171 _cell_measurement_theta_max 25.029 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.946 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details 'Bruker XPREP v5.1 (Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_detector_area_resol_mean ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 2885 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 24.99 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _reflns_number_total 2517 _reflns_number_gt 2021 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'Bruker Shelxtl v6.10 (Bruker, 2000)' _computing_molecular_graphics 'Bruker Shelxtl v6.10 (Bruker, 2000)' _computing_publication_material 'Bruker Shelxtl v6.10 (Bruker, 2000)' _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^)+(0.0401P)^2^+0.5052P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0008(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(11) _refine_ls_number_reflns 2517 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.191 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.041 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 1.10016(13) 0.90709(8) 0.01838(7) 0.0513(3) Uani 1 1 d . . . C1 C 1.2391(5) 0.8156(3) 0.3416(2) 0.0344(8) Uani 1 1 d . . . C2 C 1.1454(5) 0.8605(3) 0.4089(2) 0.0440(10) Uani 1 1 d . . . H2A H 1.1608 0.9300 0.4221 0.053 Uiso 1 1 calc R . . C3 C 1.0283(5) 0.7982(3) 0.4555(2) 0.0507(10) Uani 1 1 d . . . H3A H 0.9624 0.8274 0.5000 0.061 Uiso 1 1 calc R . . C4 C 1.0059(5) 0.6953(3) 0.4387(2) 0.0463(10) Uani 1 1 d . . . H4A H 0.9282 0.6557 0.4725 0.056 Uiso 1 1 calc R . . O5 O 1.0782(4) 0.5474(2) 0.34875(19) 0.0500(7) Uani 1 1 d . . . H5 H 1.020(6) 0.511(3) 0.392(3) 0.065 Uiso 1 1 d . . . C5 C 1.0998(5) 0.6490(3) 0.3704(2) 0.0356(8) Uani 1 1 d . . . C6 C 1.2136(5) 0.7119(3) 0.3238(2) 0.0355(8) Uani 1 1 d . . . O7 O 1.3121(3) 0.67906(17) 0.25280(16) 0.0401(6) Uani 1 1 d . . . C8 C 1.3469(4) 0.7762(2) 0.2099(2) 0.0334(8) Uani 1 1 d . . . H8A H 1.2329 0.7965 0.1810 0.040 Uiso 1 1 calc R . . C9 C 1.3827(5) 0.8540(2) 0.2793(2) 0.0343(8) Uani 1 1 d . . . C10 C 1.3575(6) 0.9604(3) 0.2399(2) 0.0447(10) Uani 1 1 d . . . H10A H 1.3940 1.0127 0.2807 0.054 Uiso 1 1 calc R . . H10B H 1.2281 0.9708 0.2270 0.054 Uiso 1 1 calc R . . C11 C 1.4705(5) 0.9738(3) 0.1594(2) 0.0440(9) Uani 1 1 d . . . H11A H 1.4215 1.0320 0.1279 0.053 Uiso 1 1 calc R . . H11B H 1.5964 0.9905 0.1749 0.053 Uiso 1 1 calc R . . N12 N 1.4727(4) 0.8806(2) 0.1023(2) 0.0388(8) Uani 1 1 d . . . H12 H 1.377(6) 0.882(3) 0.083(2) 0.047 Uiso 1 1 d . . . C12A C 1.5968(6) 0.8955(3) 0.0288(2) 0.0530(10) Uani 1 1 d . . . H12A H 1.5735 0.9618 0.0037 0.080 Uiso 1 1 calc R . . H12B H 1.5745 0.8421 -0.0122 0.080 Uiso 1 1 calc R . . H12C H 1.7228 0.8921 0.0473 0.080 Uiso 1 1 calc R . . C13 C 1.4992(5) 0.7764(3) 0.1452(2) 0.0391(9) Uani 1 1 d . . . H13A H 1.4761 0.7214 0.1038 0.047 Uiso 1 1 calc R . . C14 C 1.6896(5) 0.7619(3) 0.1827(3) 0.0487(11) Uani 1 1 d . . . H14A H 1.7021 0.6905 0.2003 0.058 Uiso 1 1 calc R . . H14B H 1.7800 0.7742 0.1385 0.058 Uiso 1 1 calc R . . C15 C 1.7357(5) 0.8306(3) 0.2574(3) 0.0533(11) Uani 1 1 d . . . H15A H 1.7659 0.8993 0.2372 0.064 Uiso 1 1 calc R . . H15B H 1.8431 0.8033 0.2865 0.064 Uiso 1 1 calc R . . C16 C 1.5747(5) 0.8374(3) 0.3195(2) 0.0445(10) Uani 1 1 d . . . H16A H 1.5983 0.8939 0.3585 0.053 Uiso 1 1 calc R . . H16B H 1.5713 0.7742 0.3525 0.053 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 0.0340(5) 0.0593(6) 0.0606(6) -0.0183(5) -0.0071(5) 0.0071(5) C1 0.0272(18) 0.041(2) 0.0346(18) -0.0014(17) -0.0009(15) -0.0006(15) C2 0.046(2) 0.051(2) 0.035(2) -0.0093(17) -0.0034(17) 0.0019(18) C3 0.045(2) 0.069(3) 0.038(2) -0.003(2) 0.0046(18) 0.007(2) C4 0.038(2) 0.062(3) 0.039(2) 0.009(2) 0.0102(18) -0.0002(19) O5 0.0432(17) 0.0401(15) 0.0668(18) 0.0075(13) 0.0124(15) -0.0043(12) C5 0.0267(17) 0.043(2) 0.0368(19) 0.0064(16) -0.0032(17) 0.0012(17) C6 0.0251(18) 0.042(2) 0.0392(19) 0.0000(17) 0.0007(15) 0.0026(15) O7 0.0370(14) 0.0307(12) 0.0525(15) -0.0001(12) 0.0144(12) -0.0032(11) C8 0.0266(18) 0.0311(18) 0.0425(19) 0.0055(16) 0.0024(15) -0.0002(15) C9 0.0305(19) 0.0332(18) 0.0394(19) 0.0005(15) -0.0021(16) -0.0014(15) C10 0.046(2) 0.033(2) 0.055(2) -0.0052(18) 0.0032(19) 0.0018(16) C11 0.042(2) 0.0339(19) 0.056(2) 0.0061(18) -0.0094(19) 0.0000(17) N12 0.0261(15) 0.0463(18) 0.0440(18) 0.0062(15) -0.0014(14) -0.0003(14) C12A 0.0378(19) 0.069(3) 0.052(2) 0.014(2) 0.010(2) -0.002(2) C13 0.039(2) 0.0311(18) 0.047(2) 0.0023(17) 0.0094(18) -0.0021(16) C14 0.034(2) 0.050(2) 0.063(3) 0.020(2) 0.0132(19) 0.0125(19) C15 0.031(2) 0.064(3) 0.064(3) 0.017(2) -0.008(2) 0.001(2) C16 0.033(2) 0.055(2) 0.046(2) 0.0057(19) -0.0088(17) -0.0088(19) _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 C1 C6 1.383(5) . ? C1 C2 1.388(5) . ? C1 C9 1.517(5) . ? C2 C3 1.383(5) . ? C2 H2A 0.9300 . ? C3 C4 1.368(6) . ? C3 H3A 0.9300 . ? C4 C5 1.408(5) . ? C4 H4A 0.9300 . ? O5 C5 1.367(4) . ? O5 H5 0.93(4) . ? C5 C6 1.373(5) . ? C6 O7 1.395(4) . ? O7 C8 1.450(4) . ? C8 C13 1.503(5) . ? C8 C9 1.511(5) . ? C8 H8A 0.9800 . ? C9 C10 1.521(5) . ? C9 C16 1.545(5) . ? C10 C11 1.523(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N12 1.505(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? N12 C12A 1.482(5) . ? N12 C13 1.520(4) . ? N12 H12 0.76(4) . ? C12A H12A 0.9600 . ? C12A H12B 0.9600 . ? C12A H12C 0.9600 . ? C13 C14 1.514(5) . ? C13 H13A 0.9800 . ? C14 C15 1.515(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.527(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.8(3) . . ? C6 C1 C9 106.1(3) . . ? C2 C1 C9 134.0(3) . . ? C3 C2 C1 117.6(4) . . ? C3 C2 H2A 121.2 . . ? C1 C2 H2A 121.2 . . ? C4 C3 C2 122.5(4) . . ? C4 C3 H3A 118.8 . . ? C2 C3 H3A 118.8 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C5 O5 H5 111(3) . . ? O5 C5 C6 120.3(3) . . ? O5 C5 C4 123.0(3) . . ? C6 C5 C4 116.7(3) . . ? C5 C6 C1 123.1(3) . . ? C5 C6 O7 123.9(3) . . ? C1 C6 O7 113.0(3) . . ? C6 O7 C8 101.6(2) . . ? O7 C8 C13 116.6(3) . . ? O7 C8 C9 105.6(3) . . ? C13 C8 C9 111.4(3) . . ? O7 C8 H8A 107.6 . . ? C13 C8 H8A 107.6 . . ? C9 C8 H8A 107.6 . . ? C8 C9 C1 97.7(3) . . ? C8 C9 C10 106.7(3) . . ? C1 C9 C10 118.6(3) . . ? C8 C9 C16 111.1(3) . . ? C1 C9 C16 107.8(3) . . ? C10 C9 C16 113.7(3) . . ? C9 C10 C11 112.3(3) . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? N12 C11 C10 114.5(3) . . ? N12 C11 H11A 108.6 . . ? C10 C11 H11A 108.6 . . ? N12 C11 H11B 108.6 . . ? C10 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C12A N12 C11 111.8(3) . . ? C12A N12 C13 112.8(3) . . ? C11 N12 C13 116.5(3) . . ? C12A N12 H12 104(3) . . ? C11 N12 H12 102(3) . . ? C13 N12 H12 108(3) . . ? N12 C12A H12A 109.5 . . ? N12 C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? N12 C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C8 C13 C14 113.8(3) . . ? C8 C13 N12 102.2(3) . . ? C14 C13 N12 113.5(3) . . ? C8 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? N12 C13 H13A 109.0 . . ? C15 C14 C13 115.7(3) . . ? C15 C14 H14A 108.4 . . ? C13 C14 H14A 108.4 . . ? C15 C14 H14B 108.4 . . ? C13 C14 H14B 108.4 . . ? H14A C14 H14B 107.4 . . ? C14 C15 C16 111.4(3) . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C9 115.6(3) . . ? C15 C16 H16A 108.4 . . ? C9 C16 H16A 108.4 . . ? C15 C16 H16B 108.4 . . ? C9 C16 H16B 108.4 . . ? H16A C16 H16B 107.4 . . ? 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 C6 C1 C2 C3 -0.2(5) . . . . ? C9 C1 C2 C3 -176.5(4) . . . . ? C1 C2 C3 C4 1.4(6) . . . . ? C2 C3 C4 C5 -1.7(6) . . . . ? C3 C4 C5 O5 -177.7(4) . . . . ? C3 C4 C5 C6 0.7(5) . . . . ? O5 C5 C6 C1 179.0(3) . . . . ? C4 C5 C6 C1 0.5(5) . . . . ? O5 C5 C6 O7 0.4(5) . . . . ? C4 C5 C6 O7 -178.0(3) . . . . ? C2 C1 C6 C5 -0.7(5) . . . . ? C9 C1 C6 C5 176.5(3) . . . . ? C2 C1 C6 O7 177.9(3) . . . . ? C9 C1 C6 O7 -4.8(4) . . . . ? C5 C6 O7 C8 158.6(3) . . . . ? C1 C6 O7 C8 -20.1(4) . . . . ? C6 O7 C8 C13 161.5(3) . . . . ? C6 O7 C8 C9 37.2(3) . . . . ? O7 C8 C9 C1 -38.9(3) . . . . ? C13 C8 C9 C1 -166.3(3) . . . . ? O7 C8 C9 C10 -161.9(3) . . . . ? C13 C8 C9 C10 70.6(4) . . . . ? O7 C8 C9 C16 73.7(3) . . . . ? C13 C8 C9 C16 -53.8(4) . . . . ? C6 C1 C9 C8 26.2(3) . . . . ? C2 C1 C9 C8 -157.2(4) . . . . ? C6 C1 C9 C10 140.0(3) . . . . ? C2 C1 C9 C10 -43.4(6) . . . . ? C6 C1 C9 C16 -89.0(3) . . . . ? C2 C1 C9 C16 87.7(5) . . . . ? C8 C9 C10 C11 -51.9(4) . . . . ? C1 C9 C10 C11 -160.8(3) . . . . ? C16 C9 C10 C11 70.9(4) . . . . ? C9 C10 C11 N12 40.6(4) . . . . ? C10 C11 N12 C12A -175.3(3) . . . . ? C10 C11 N12 C13 -43.7(4) . . . . ? O7 C8 C13 C14 -67.6(4) . . . . ? C9 C8 C13 C14 53.6(4) . . . . ? O7 C8 C13 N12 169.6(3) . . . . ? C9 C8 C13 N12 -69.2(3) . . . . ? C12A N12 C13 C8 -174.1(3) . . . . ? C11 N12 C13 C8 54.6(4) . . . . ? C12A N12 C13 C14 62.8(4) . . . . ? C11 N12 C13 C14 -68.4(4) . . . . ? C8 C13 C14 C15 -49.0(4) . . . . ? N12 C13 C14 C15 67.3(4) . . . . ? C13 C14 C15 C16 43.2(4) . . . . ? C14 C15 C16 C9 -44.8(5) . . . . ? C8 C9 C16 C15 51.0(4) . . . . ? C1 C9 C16 C15 157.0(3) . . . . ? C10 C9 C16 C15 -69.3(4) . . . . ? #========================================================================== # END OF CIF #==========================================================================