#------------------------------------------------------------------------------ #$Date: 2020-02-20 05:45:33 +0200 (Thu, 20 Feb 2020) $ #$Revision: 248302 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557341.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1557341 loop_ _publ_author_name 'Lin, Qianchi' 'Hu, Bowen' 'Xu, Xi' 'Dong, Shunxi' 'Liu, Xiaohua' 'Feng, Xiaoming' _publ_section_title ; Chiral N,N′-Dioxide/Mg(OTf)2 Complex-Catalyzed Asymmetric [2,3]-Rearrangement of in situ Generated Ammonium Salts ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC06342K _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_sum 'C15 H21 Cl0 N O2' _chemical_formula_weight 247.33 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2019-10-23 deposited with the CCDC. 2020-02-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.5161(5) _cell_length_b 10.5750(6) _cell_length_c 15.9557(9) _cell_measurement_reflns_used 9006 _cell_measurement_temperature 170(2) _cell_measurement_theta_max 68.44 _cell_measurement_theta_min 2.77 _cell_volume 1436.93(14) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 170(2) _diffrn_measured_fraction_theta_full 0.962 _diffrn_measured_fraction_theta_max 0.960 _diffrn_measurement_device_type 'BRUKER D8 VENTURE PHOTON II' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_unetI/netI 0.0195 _diffrn_reflns_Laue_measured_fraction_full 0.962 _diffrn_reflns_Laue_measured_fraction_max 0.960 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 9239 _diffrn_reflns_point_group_measured_fraction_full 0.962 _diffrn_reflns_point_group_measured_fraction_max 0.959 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.431 _diffrn_reflns_theta_min 5.017 _exptl_absorpt_coefficient_mu 0.597 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.5185 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour COLORLESS _exptl_crystal_density_diffrn 1.143 _exptl_crystal_description BLOCK _exptl_crystal_F_000 536 _refine_diff_density_max 0.137 _refine_diff_density_min -0.113 _refine_diff_density_rms 0.023 _refine_ls_abs_structure_details ; Flack x determined using 1050 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 2537 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0313 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.1459P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0922 _refine_ls_wR_factor_ref 0.0922 _reflns_Friedel_coverage 0.718 _reflns_Friedel_fraction_full 0.961 _reflns_Friedel_fraction_max 0.958 _reflns_number_gt 2531 _reflns_number_total 2537 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06342k2.cif _cod_data_source_block cu_LQC20190608_1_0m_a _cod_database_code 1557341 _shelx_shelxl_version_number 2016/6 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; TITL cu_LQC20190608_1_0m_a.res in P2(1)2(1)2(1) cu_LQC20190608_1_0m_a.res created by SHELXL-2016/6 at 14:47:17 on 10-Jun-2019 REM Old TITL cu_LQC20190608_1_0m in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.128, Rweak 0.033, Alpha 0.007, Orientation as input REM Flack x = 0.058 ( 0.036 ) from Parsons' quotients REM Formula found by SHELXT: C14 N2 O2 CELL 1.54178 8.5161 10.5750 15.9557 90.000 90.000 90.000 ZERR 4 0.0005 0.0006 0.0009 0.000 0.000 0.000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H CL N O UNIT 60 84 0 4 8 ACTA TEMP -103.140 L.S. 10 BOND $H omit 3 3 3 LIST 4 htab EQIV $1 -x+1, y+1/2, -z+1/2 HTAB C11 O1_$1 HTAB C14 O1 conf FMAP 2 PLAN 20 WGHT 0.063000 0.145900 FVAR 2.47132 O1 5 0.407799 0.166395 0.278304 11.00000 0.04845 0.03554 = 0.06857 0.00798 0.01549 -0.00388 N1 4 0.530866 0.313948 0.118349 11.00000 0.03805 0.03801 = 0.04051 0.00444 -0.00327 -0.00503 C1 1 0.873990 0.326697 0.486801 11.00000 0.04936 0.06738 = 0.03469 0.00369 -0.00016 -0.00957 AFIX 43 H1 2 0.911936 0.340794 0.542006 11.00000 -1.20000 AFIX 0 C2 1 0.809933 0.424494 0.441462 11.00000 0.05397 0.04788 = 0.04111 -0.00613 0.00401 -0.00294 AFIX 43 H2 2 0.803497 0.506480 0.465557 11.00000 -1.20000 AFIX 0 O2 5 0.331934 0.368341 0.285790 11.00000 0.03512 0.04232 = 0.05857 0.00520 0.00927 0.00393 C3 1 0.754555 0.404273 0.360668 11.00000 0.04406 0.03764 = 0.04015 -0.00061 0.00239 0.00317 AFIX 43 H3 2 0.710178 0.472599 0.330119 11.00000 -1.20000 AFIX 0 C4 1 0.763311 0.285260 0.324004 11.00000 0.02487 0.03502 = 0.03746 0.00211 0.00535 -0.00123 C5 1 0.827394 0.187323 0.370833 11.00000 0.03790 0.03715 = 0.04642 0.00558 0.00431 0.00298 AFIX 43 H5 2 0.833398 0.104985 0.347240 11.00000 -1.20000 AFIX 0 C6 1 0.882653 0.207630 0.451281 11.00000 0.04873 0.05640 = 0.04566 0.01681 -0.00043 0.00444 AFIX 43 H6 2 0.926685 0.139543 0.482204 11.00000 -1.20000 AFIX 0 C7 1 0.716506 0.258914 0.233228 11.00000 0.03175 0.02697 = 0.03878 -0.00032 0.00190 -0.00136 AFIX 13 H7 2 0.696896 0.165988 0.228207 11.00000 -1.20000 AFIX 0 C9 1 0.884099 0.427313 0.156448 11.00000 0.03926 0.04401 = 0.04572 -0.00083 0.00798 -0.00922 AFIX 137 H9A 2 0.977280 0.434081 0.120687 11.00000 -1.50000 H9B 2 0.902331 0.473105 0.208951 11.00000 -1.50000 H9C 2 0.793499 0.463989 0.127409 11.00000 -1.50000 AFIX 0 C8 1 0.852342 0.291162 0.175208 11.00000 0.03096 0.04111 = 0.03459 -0.00440 0.00033 -0.00097 C10 1 0.945065 0.200134 0.146578 11.00000 0.04894 0.04967 = 0.05116 -0.00320 0.01078 0.00797 AFIX 93 H10A 2 1.033994 0.220793 0.113343 11.00000 -1.20000 H10B 2 0.922556 0.114268 0.159306 11.00000 -1.20000 AFIX 0 C11 1 0.564489 0.326826 0.208386 11.00000 0.02921 0.02818 = 0.04047 0.00075 -0.00052 -0.00218 AFIX 13 H11 2 0.577349 0.418819 0.221172 11.00000 -1.20000 AFIX 0 C12 1 0.429257 0.275775 0.262119 11.00000 0.02992 0.03471 = 0.03952 0.00059 -0.00274 -0.00139 C13 1 0.192578 0.328097 0.330176 11.00000 0.03335 0.07216 = 0.06223 0.01510 0.01124 0.01083 AFIX 137 H13A 2 0.123039 0.282566 0.291651 11.00000 -1.50000 H13B 2 0.137749 0.402292 0.352491 11.00000 -1.50000 H13C 2 0.222504 0.272162 0.376468 11.00000 -1.50000 AFIX 0 C14 1 0.501160 0.185861 0.089825 11.00000 0.08951 0.04774 = 0.04543 -0.00209 -0.01639 -0.01414 AFIX 137 H14A 2 0.493811 0.184944 0.028534 11.00000 -1.50000 H14B 2 0.402285 0.155424 0.113919 11.00000 -1.50000 H14C 2 0.587322 0.130715 0.107761 11.00000 -1.50000 AFIX 0 C15 1 0.406119 0.399794 0.091794 11.00000 0.04389 0.06068 = 0.05037 0.01686 -0.00534 -0.00135 AFIX 137 H15A 2 0.402665 0.403019 0.030439 11.00000 -1.50000 H15B 2 0.426870 0.484615 0.113915 11.00000 -1.50000 H15C 2 0.305099 0.369360 0.113206 11.00000 -1.50000 AFIX 0 HKLF 4 REM cu_LQC20190608_1_0m_a.res in P2(1)2(1)2(1) REM R1 = 0.0313 for 2531 Fo > 4sig(Fo) and 0.0314 for all 2537 data REM 167 parameters refined using 0 restraints END WGHT 0.0492 0.1797 REM Instructions for potential hydrogen bonds HTAB C11 O1_$1 HTAB C14 O1 REM Highest difference peak 0.137, deepest hole -0.113, 1-sigma level 0.023 Q1 1 0.1095 0.3766 0.3079 11.00000 0.05 0.14 Q2 1 0.7402 0.2790 0.2790 11.00000 0.05 0.13 Q3 1 0.7833 0.2784 0.2019 11.00000 0.05 0.12 Q4 1 0.5429 0.3180 0.1590 11.00000 0.05 0.12 Q5 1 0.6619 0.3153 0.2225 11.00000 0.05 0.12 Q6 1 0.7477 0.2176 0.3522 11.00000 0.05 0.11 Q7 1 0.8407 0.3617 0.1610 11.00000 0.05 0.11 Q8 1 0.7984 0.4844 0.1648 11.00000 0.05 0.10 Q9 1 0.7152 0.3924 0.4193 11.00000 0.05 0.10 Q10 1 0.2047 0.3537 0.3880 11.00000 0.05 0.10 Q11 1 0.7940 0.3510 0.3364 11.00000 0.05 0.09 Q12 1 0.5212 0.2448 0.1066 11.00000 0.05 0.09 Q13 1 0.1428 0.2055 0.3015 11.00000 0.05 0.09 Q14 1 0.5284 0.1165 0.1257 11.00000 0.05 0.08 Q15 1 0.4059 0.1744 0.0569 11.00000 0.05 0.08 Q16 1 0.8674 0.2447 0.1326 11.00000 0.05 0.08 Q17 1 0.7241 0.3394 0.3440 11.00000 0.05 0.08 Q18 1 0.5048 0.3083 0.2359 11.00000 0.05 0.08 Q19 1 0.5777 0.1376 0.1956 11.00000 0.05 0.08 Q20 1 0.2930 0.1937 0.2561 11.00000 0.05 0.07 ; _shelx_res_checksum 54869 loop_ _space_group_symop_operation_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' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.40780(17) 0.16639(12) 0.27830(10) 0.0509(4) Uani 1 1 d . . . . . N1 N 0.53087(17) 0.31395(14) 0.11835(9) 0.0389(4) Uani 1 1 d . . . . . C1 C 0.8740(2) 0.3267(2) 0.48680(11) 0.0505(5) Uani 1 1 d . . . . . H1 H 0.911936 0.340794 0.542006 0.061 Uiso 1 1 calc R U . . . C2 C 0.8099(2) 0.42449(19) 0.44146(12) 0.0477(5) Uani 1 1 d . . . . . H2 H 0.803497 0.506480 0.465557 0.057 Uiso 1 1 calc R U . . . O2 O 0.33193(15) 0.36834(12) 0.28579(9) 0.0453(3) Uani 1 1 d . . . . . C3 C 0.7546(2) 0.40427(17) 0.36067(11) 0.0406(4) Uani 1 1 d . . . . . H3 H 0.710178 0.472599 0.330119 0.049 Uiso 1 1 calc R U . . . C4 C 0.76331(17) 0.28526(16) 0.32400(10) 0.0324(3) Uani 1 1 d . . . . . C5 C 0.8274(2) 0.18732(17) 0.37083(11) 0.0405(4) Uani 1 1 d . . . . . H5 H 0.833398 0.104985 0.347240 0.049 Uiso 1 1 calc R U . . . C6 C 0.8827(2) 0.2076(2) 0.45128(12) 0.0503(5) Uani 1 1 d . . . . . H6 H 0.926685 0.139543 0.482204 0.060 Uiso 1 1 calc R U . . . C7 C 0.71651(19) 0.25891(15) 0.23323(10) 0.0325(4) Uani 1 1 d . . . . . H7 H 0.696896 0.165988 0.228207 0.039 Uiso 1 1 calc R U . . . C9 C 0.8841(2) 0.42731(17) 0.15645(12) 0.0430(4) Uani 1 1 d . . . . . H9A H 0.977280 0.434081 0.120687 0.064 Uiso 1 1 calc R U . . . H9B H 0.902331 0.473105 0.208951 0.064 Uiso 1 1 calc R U . . . H9C H 0.793499 0.463989 0.127409 0.064 Uiso 1 1 calc R U . . . C8 C 0.85234(19) 0.29116(17) 0.17521(10) 0.0356(4) Uani 1 1 d . . . . . C10 C 0.9451(2) 0.2001(2) 0.14658(12) 0.0499(5) Uani 1 1 d . . . . . H10A H 1.033994 0.220793 0.113343 0.060 Uiso 1 1 calc R U . . . H10B H 0.922556 0.114268 0.159306 0.060 Uiso 1 1 calc R U . . . C11 C 0.56449(18) 0.32683(14) 0.20839(10) 0.0326(4) Uani 1 1 d . . . . . H11 H 0.577349 0.418819 0.221172 0.039 Uiso 1 1 calc R U . . . C12 C 0.42926(19) 0.27578(16) 0.26212(10) 0.0347(4) Uani 1 1 d . . . . . C13 C 0.1926(2) 0.3281(2) 0.33018(14) 0.0559(5) Uani 1 1 d . . . . . H13A H 0.123039 0.282566 0.291651 0.084 Uiso 1 1 calc R U . . . H13B H 0.137749 0.402292 0.352491 0.084 Uiso 1 1 calc R U . . . H13C H 0.222504 0.272162 0.376468 0.084 Uiso 1 1 calc R U . . . C14 C 0.5012(3) 0.18586(19) 0.08983(13) 0.0609(6) Uani 1 1 d . . . . . H14A H 0.493811 0.184944 0.028534 0.091 Uiso 1 1 calc R U . . . H14B H 0.402285 0.155424 0.113919 0.091 Uiso 1 1 calc R U . . . H14C H 0.587322 0.130715 0.107761 0.091 Uiso 1 1 calc R U . . . C15 C 0.4061(2) 0.3998(2) 0.09179(13) 0.0516(5) Uani 1 1 d . . . . . H15A H 0.402665 0.403019 0.030439 0.077 Uiso 1 1 calc R U . . . H15B H 0.426870 0.484615 0.113915 0.077 Uiso 1 1 calc R U . . . H15C H 0.305099 0.369360 0.113206 0.077 Uiso 1 1 calc R U . . . 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 0.0485(7) 0.0355(7) 0.0686(9) 0.0080(6) 0.0155(7) -0.0039(6) N1 0.0381(7) 0.0380(8) 0.0405(7) 0.0044(6) -0.0033(6) -0.0050(6) C1 0.0494(10) 0.0674(13) 0.0347(8) 0.0037(8) -0.0002(7) -0.0096(9) C2 0.0540(11) 0.0479(10) 0.0411(9) -0.0061(8) 0.0040(8) -0.0029(9) O2 0.0351(7) 0.0423(7) 0.0586(8) 0.0052(6) 0.0093(6) 0.0039(5) C3 0.0441(9) 0.0376(9) 0.0402(9) -0.0006(7) 0.0024(7) 0.0032(7) C4 0.0249(7) 0.0350(8) 0.0375(8) 0.0021(6) 0.0053(6) -0.0012(6) C5 0.0379(8) 0.0372(9) 0.0464(9) 0.0056(7) 0.0043(7) 0.0030(7) C6 0.0487(11) 0.0564(11) 0.0457(10) 0.0168(9) -0.0004(8) 0.0044(9) C7 0.0317(7) 0.0270(7) 0.0388(8) -0.0003(6) 0.0019(6) -0.0014(6) C9 0.0393(9) 0.0440(9) 0.0457(9) -0.0008(8) 0.0080(7) -0.0092(7) C8 0.0310(7) 0.0411(8) 0.0346(8) -0.0044(7) 0.0003(6) -0.0010(7) C10 0.0489(10) 0.0497(10) 0.0512(10) -0.0032(9) 0.0108(8) 0.0080(9) C11 0.0292(8) 0.0282(7) 0.0405(8) 0.0007(6) -0.0005(6) -0.0022(6) C12 0.0299(7) 0.0347(8) 0.0395(8) 0.0006(6) -0.0027(6) -0.0014(6) C13 0.0334(9) 0.0722(14) 0.0622(12) 0.0151(11) 0.0112(8) 0.0108(9) C14 0.0895(16) 0.0477(11) 0.0454(10) -0.0021(9) -0.0164(11) -0.0141(11) C15 0.0439(10) 0.0607(12) 0.0504(10) 0.0169(9) -0.0053(8) -0.0013(9) 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' Cl Cl 0.3639 0.7018 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 N1 C15 111.25(17) . . ? C14 N1 C11 115.25(14) . . ? C15 N1 C11 111.56(14) . . ? C2 C1 C6 119.37(17) . . ? C2 C1 H1 120.3 . . ? C6 C1 H1 120.3 . . ? C1 C2 C3 120.47(18) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C12 O2 C13 115.57(15) . . ? C4 C3 C2 120.78(17) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 118.03(15) . . ? C5 C4 C7 118.46(15) . . ? C3 C4 C7 123.38(15) . . ? C6 C5 C4 121.13(17) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C1 C6 C5 120.22(18) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C4 109.74(12) . . ? C8 C7 C11 112.34(13) . . ? C4 C7 C11 112.34(13) . . ? C8 C7 H7 107.4 . . ? C4 C7 H7 107.4 . . ? C11 C7 H7 107.4 . . ? 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 . . ? C10 C8 C9 121.49(16) . . ? C10 C8 C7 120.00(17) . . ? C9 C8 C7 118.39(14) . . ? C8 C10 H10A 120.0 . . ? C8 C10 H10B 120.0 . . ? H10A C10 H10B 120.0 . . ? N1 C11 C7 111.94(13) . . ? N1 C11 C12 111.54(12) . . ? C7 C11 C12 108.95(12) . . ? N1 C11 H11 108.1 . . ? C7 C11 H11 108.1 . . ? C12 C11 H11 108.1 . . ? O1 C12 O2 123.43(16) . . ? O1 C12 C11 125.05(16) . . ? O2 C12 C11 111.45(14) . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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 C12 1.199(2) . ? N1 C14 1.451(2) . ? N1 C15 1.460(2) . ? N1 C11 1.471(2) . ? C1 C2 1.375(3) . ? C1 C6 1.383(3) . ? C1 H1 0.9500 . ? C2 C3 1.389(3) . ? C2 H2 0.9500 . ? O2 C12 1.337(2) . ? O2 C13 1.446(2) . ? C3 C4 1.390(2) . ? C3 H3 0.9500 . ? C4 C5 1.389(2) . ? C4 C7 1.528(2) . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.520(2) . ? C7 C11 1.533(2) . ? C7 H7 1.0000 . ? C9 C8 1.495(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C8 C10 1.326(3) . ? C10 H10A 0.9500 . ? C10 H10B 0.9500 . ? C11 C12 1.534(2) . ? C11 H11 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 C11 H11 O1 1.00 2.62 3.605(2) 167.9 3_655 C14 H14B O1 0.98 2.63 3.117(3) 111.2 . 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 C6 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 0.7(3) . . . . ? C2 C3 C4 C7 -175.06(16) . . . . ? C3 C4 C5 C6 -0.7(2) . . . . ? C7 C4 C5 C6 175.21(16) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? C4 C5 C6 C1 0.4(3) . . . . ? C5 C4 C7 C8 -92.42(17) . . . . ? C3 C4 C7 C8 83.29(19) . . . . ? C5 C4 C7 C11 141.84(14) . . . . ? C3 C4 C7 C11 -42.5(2) . . . . ? C4 C7 C8 C10 99.51(19) . . . . ? C11 C7 C8 C10 -134.75(17) . . . . ? C4 C7 C8 C9 -76.48(18) . . . . ? C11 C7 C8 C9 49.27(19) . . . . ? C14 N1 C11 C7 64.0(2) . . . . ? C15 N1 C11 C7 -167.93(13) . . . . ? C14 N1 C11 C12 -58.4(2) . . . . ? C15 N1 C11 C12 69.70(17) . . . . ? C8 C7 C11 N1 48.57(17) . . . . ? C4 C7 C11 N1 172.88(13) . . . . ? C8 C7 C11 C12 172.40(13) . . . . ? C4 C7 C11 C12 -63.29(16) . . . . ? C13 O2 C12 O1 -2.4(3) . . . . ? C13 O2 C12 C11 174.47(15) . . . . ? N1 C11 C12 O1 81.0(2) . . . . ? C7 C11 C12 O1 -43.1(2) . . . . ? N1 C11 C12 O2 -95.88(16) . . . . ? C7 C11 C12 O2 140.05(14) . . . . ?