#------------------------------------------------------------------------------ #$Date: 2019-07-14 05:39:16 +0300 (Sun, 14 Jul 2019) $ #$Revision: 217019 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/69/7156972.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_7156972 loop_ _publ_author_name 'Ahire, Milind M.' 'Pol, Mahesh D.' 'Kavale, Dattatry S.' 'Gonnade, Rajesh G.' 'Mhaske, Santosh B.' _publ_section_title ; Stereoselective Construction of Deoxy-Cruciferane Alkaloids by NHC-Catalyzed Intramolecular Annulation of Homoenolate with Quinazolinone ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB01243E _journal_year 2019 _chemical_absolute_configuration ad _chemical_formula_moiety 'C17 H12 N2 O2' _chemical_formula_sum 'C17 H12 N2 O2' _chemical_formula_weight 276.29 _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' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-03-21 deposited with the CCDC. 2019-07-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.2455(12) _cell_length_b 11.3533(16) _cell_length_c 13.652(2) _cell_measurement_reflns_used 9899 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 72.43 _cell_measurement_theta_min 3.24 _cell_volume 1278.0(3) _computing_cell_refinement 'SAINT (Bruker, 2016)' _computing_data_collection 'APEX3 (Bruker, 2016)' _computing_data_reduction 'SAINT (Bruker, 2016)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'Photon II CPAD Area Detector' _diffrn_detector_area_resol_mean 7.39 _diffrn_measured_fraction_theta_full 0.944 _diffrn_measured_fraction_theta_max 0.937 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'multilayer mirrors' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_unetI/netI 0.0291 _diffrn_reflns_Laue_measured_fraction_full 0.944 _diffrn_reflns_Laue_measured_fraction_max 0.937 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 16043 _diffrn_reflns_point_group_measured_fraction_full 0.946 _diffrn_reflns_point_group_measured_fraction_max 0.937 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 72.427 _diffrn_reflns_theta_min 6.270 _diffrn_source 'micro-focus sealed tube' _diffrn_source_type 'Incoatech I\mS HB' _exptl_absorpt_coefficient_mu 0.779 _exptl_absorpt_correction_T_max 0.919 _exptl_absorpt_correction_T_min 0.778 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (BRUKER, 2016)' _exptl_crystal_colour COLOURLESS _exptl_crystal_density_diffrn 1.436 _exptl_crystal_description NEEDLE _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.340 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.228 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.043 _refine_ls_abs_structure_details ; Flack x determined using 967 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.08(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 2369 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0334 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+0.3343P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0877 _refine_ls_wR_factor_ref 0.0914 _reflns_Friedel_coverage 0.720 _reflns_Friedel_fraction_full 0.949 _reflns_Friedel_fraction_max 0.937 _reflns_number_gt 2301 _reflns_number_total 2369 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob01243e2.cif _cod_data_source_block cu_ma_1_r_0m _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_absolute_configuration' value 'AD' changed to 'ad' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to 'multi-scan' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 7156972 _shelx_shelxl_version_number 2014/7 _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_estimated_absorpt_t_min 0.778 _shelx_estimated_absorpt_t_max 0.919 _shelx_res_file ; cu_ma_1_r_0m.res created by SHELXL-2014/7 TITL cu_ma_1_r_0m_a.res in P2(1)2(1)2(1) CELL 1.54178 8.2455 11.3533 13.6516 90.000 90.000 90.000 ZERR 4.00 0.0012 0.0016 0.0020 0.000 0.000 0.000 LATT -1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N O UNIT 68 48 8 8 OMIT 9 0 2 OMIT 9 0 7 OMIT 8 0 2 OMIT -9 3 7 OMIT -9 1 4 OMIT 9 1 4 OMIT 9 1 6 OMIT 10 0 3 OMIT 10 0 2 OMIT -10 2 1 OMIT 9 0 4 OMIT -9 2 6 OMIT -10 1 1 OMIT 10 1 1 OMIT -9 1 5 OMIT 10 1 0 OMIT 8 0 0 OMIT 10 0 1 OMIT 10 2 0 OMIT 9 0 3 OMIT 8 2 5 OMIT 9 0 5 OMIT -8 4 1 L.S. 30 ACTA BOND $H FMAP 2 PLAN 10 SIZE 0.34 0.13 0.11 CONF HTAB C16 O1 EQIV $1 -x+3/2, -y+1, z-1/2 HTAB C11 O1_$1 TEMP -173.150 WGHT 0.054400 0.334300 FVAR 1.75015 O2 4 0.576294 0.180124 0.326285 11.00000 0.03648 0.03933 = 0.03258 -0.01490 -0.00901 0.00310 O1 4 0.589749 0.390273 0.698789 11.00000 0.03756 0.02458 = 0.01882 -0.00473 0.00423 0.00035 N1 3 0.702977 0.428741 0.549947 11.00000 0.01739 0.02135 = 0.01923 -0.00214 0.00097 0.00022 N2 3 0.744920 0.269324 0.437954 11.00000 0.01674 0.02721 = 0.01993 -0.00455 0.00081 0.00113 C4 1 0.708898 0.030215 0.670618 11.00000 0.01825 0.02372 = 0.03719 0.00401 -0.00130 -0.00302 AFIX 43 H4 2 0.698955 -0.023526 0.723619 11.00000 -1.20000 AFIX 0 C5 1 0.690402 0.149837 0.686474 11.00000 0.02039 0.02652 = 0.02624 -0.00024 -0.00131 -0.00403 AFIX 43 H5 2 0.669203 0.178019 0.750734 11.00000 -1.20000 AFIX 0 C6 1 0.702553 0.229173 0.609245 11.00000 0.01516 0.02036 = 0.02436 -0.00311 -0.00055 -0.00270 C7 1 0.662063 0.356061 0.625575 11.00000 0.01833 0.02277 = 0.01894 -0.00266 -0.00266 -0.00204 C17 1 0.641612 0.542245 0.529121 11.00000 0.01561 0.02070 = 0.02453 0.00164 -0.00482 -0.00327 C12 1 0.663587 0.567350 0.429777 11.00000 0.01641 0.02712 = 0.02622 0.00216 -0.00140 -0.00378 C13 1 0.606209 0.672320 0.391774 11.00000 0.02464 0.03064 = 0.03217 0.00852 -0.00465 -0.00462 AFIX 43 H13 2 0.618879 0.689733 0.324141 11.00000 -1.20000 AFIX 0 C14 1 0.529707 0.752086 0.453832 11.00000 0.02452 0.02355 = 0.04484 0.00744 -0.00757 -0.00231 AFIX 43 H14 2 0.489341 0.824181 0.428274 11.00000 -1.20000 AFIX 0 C15 1 0.511855 0.727105 0.553015 11.00000 0.02099 0.02165 = 0.04028 -0.00552 -0.00350 -0.00091 AFIX 43 H16 2 0.461726 0.783361 0.594692 11.00000 -1.20000 AFIX 0 C16 1 0.566358 0.620813 0.592254 11.00000 0.02048 0.02289 = 0.02808 -0.00345 -0.00414 -0.00203 AFIX 43 H15 2 0.552454 0.602898 0.659709 11.00000 -1.20000 AFIX 0 C1 1 0.737089 0.186259 0.515149 11.00000 0.01224 0.02441 = 0.02522 -0.00340 -0.00202 0.00100 C2 1 0.755327 0.065966 0.498644 11.00000 0.01570 0.02905 = 0.03293 -0.01107 0.00001 0.00247 AFIX 43 H2 2 0.776565 0.037183 0.434573 11.00000 -1.20000 AFIX 0 C3 1 0.742128 -0.011116 0.576732 11.00000 0.01923 0.01995 = 0.04722 -0.00606 -0.00344 0.00108 AFIX 43 H3 2 0.755903 -0.093213 0.566158 11.00000 -1.20000 AFIX 0 C9 1 0.647095 0.266653 0.355052 11.00000 0.02060 0.03713 = 0.02094 -0.00944 0.00071 0.00750 C10 1 0.645128 0.389301 0.311209 11.00000 0.02528 0.04149 = 0.01837 -0.00173 -0.00083 0.00602 AFIX 23 H10B 2 0.532842 0.419977 0.308276 11.00000 -1.20000 H10A 2 0.690346 0.388109 0.244037 11.00000 -1.20000 AFIX 0 C11 1 0.750710 0.467223 0.378914 11.00000 0.02009 0.03356 = 0.02057 0.00432 0.00289 0.00219 AFIX 13 H11 2 0.849402 0.496168 0.343800 11.00000 -1.20000 AFIX 0 C8 1 0.797212 0.385910 0.464908 11.00000 0.01582 0.02626 = 0.01965 -0.00133 0.00112 -0.00083 AFIX 13 H8 2 0.916449 0.388316 0.478142 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM cu_ma_1_r_0m_a.res in P2(1)2(1)2(1) REM R1 = 0.0334 for 2301 Fo > 4sig(Fo) and 0.0348 for all 2369 data REM 190 parameters refined using 0 restraints END WGHT 0.0544 0.3343 REM Highest difference peak 0.228, deepest hole -0.218, 1-sigma level 0.043 Q1 1 0.7145 0.2921 0.6172 11.00000 0.05 0.23 Q2 1 0.6593 0.4860 0.5429 11.00000 0.05 0.19 Q3 1 0.6960 0.5131 0.3963 11.00000 0.05 0.18 Q4 1 0.7308 0.3231 0.4540 11.00000 0.05 0.18 Q5 1 0.7962 0.0986 0.6812 11.00000 0.05 0.17 Q6 1 0.7052 0.0471 0.5391 11.00000 0.05 0.17 Q7 1 0.6901 0.1201 0.5069 11.00000 0.05 0.16 Q8 1 0.6095 0.7191 0.4342 11.00000 0.05 0.16 Q9 1 0.6340 0.4780 0.6807 11.00000 0.05 0.15 Q10 1 0.6627 0.2093 0.5573 11.00000 0.05 0.15 ; _shelx_res_checksum 4400 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' 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 O2 O 0.5763(2) 0.18012(15) 0.32629(12) 0.0361(4) Uani 1 1 d . . O1 O 0.5897(2) 0.39027(13) 0.69879(10) 0.0270(4) Uani 1 1 d . . N1 N 0.7030(2) 0.42874(14) 0.54995(12) 0.0193(4) Uani 1 1 d . . N2 N 0.7449(2) 0.26932(15) 0.43795(12) 0.0213(4) Uani 1 1 d . . C4 C 0.7089(3) 0.03021(19) 0.67062(18) 0.0264(5) Uani 1 1 d . . H4 H 0.6990 -0.0235 0.7236 0.032 Uiso 1 1 calc R U C5 C 0.6904(3) 0.14984(19) 0.68647(16) 0.0244(5) Uani 1 1 d . . H5 H 0.6692 0.1780 0.7507 0.029 Uiso 1 1 calc R U C6 C 0.7026(3) 0.22917(18) 0.60925(15) 0.0200(5) Uani 1 1 d . . C7 C 0.6621(3) 0.35606(18) 0.62557(14) 0.0200(4) Uani 1 1 d . . C17 C 0.6416(3) 0.54225(18) 0.52912(14) 0.0203(5) Uani 1 1 d . . C12 C 0.6636(3) 0.56735(19) 0.42978(15) 0.0233(5) Uani 1 1 d . . C13 C 0.6062(3) 0.6723(2) 0.39177(18) 0.0291(5) Uani 1 1 d . . H13 H 0.6189 0.6897 0.3241 0.035 Uiso 1 1 calc R U C14 C 0.5297(3) 0.75209(19) 0.45383(19) 0.0310(6) Uani 1 1 d . . H14 H 0.4893 0.8242 0.4283 0.037 Uiso 1 1 calc R U C15 C 0.5119(3) 0.72711(19) 0.55301(18) 0.0276(5) Uani 1 1 d . . H16 H 0.4617 0.7834 0.5947 0.033 Uiso 1 1 calc R U C16 C 0.5664(3) 0.62081(17) 0.59225(15) 0.0238(5) Uani 1 1 d . . H15 H 0.5525 0.6029 0.6597 0.029 Uiso 1 1 calc R U C1 C 0.7371(3) 0.18626(18) 0.51515(15) 0.0206(4) Uani 1 1 d . . C2 C 0.7553(3) 0.06597(19) 0.49864(17) 0.0259(5) Uani 1 1 d . . H2 H 0.7766 0.0372 0.4346 0.031 Uiso 1 1 calc R U C3 C 0.7421(3) -0.01112(19) 0.57673(18) 0.0288(5) Uani 1 1 d . . H3 H 0.7559 -0.0932 0.5662 0.035 Uiso 1 1 calc R U C9 C 0.6471(3) 0.2667(2) 0.35505(15) 0.0262(5) Uani 1 1 d . . C10 C 0.6451(3) 0.3893(2) 0.31121(15) 0.0284(5) Uani 1 1 d . . H10B H 0.5328 0.4200 0.3083 0.034 Uiso 1 1 calc R U H10A H 0.6903 0.3881 0.2440 0.034 Uiso 1 1 calc R U C11 C 0.7507(3) 0.46722(19) 0.37891(14) 0.0247(5) Uani 1 1 d . . H11 H 0.8494 0.4962 0.3438 0.030 Uiso 1 1 calc R U C8 C 0.7972(3) 0.38591(19) 0.46491(14) 0.0206(5) Uani 1 1 d . . H8 H 0.9164 0.3883 0.4781 0.025 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 O2 0.0365(11) 0.0393(9) 0.0326(8) -0.0149(7) -0.0090(8) 0.0031(8) O1 0.0376(10) 0.0246(7) 0.0188(7) -0.0047(6) 0.0042(6) 0.0004(7) N1 0.0174(10) 0.0213(8) 0.0192(8) -0.0021(6) 0.0010(7) 0.0002(7) N2 0.0167(11) 0.0272(8) 0.0199(8) -0.0045(7) 0.0008(7) 0.0011(7) C4 0.0182(12) 0.0237(10) 0.0372(11) 0.0040(9) -0.0013(9) -0.0030(8) C5 0.0204(13) 0.0265(11) 0.0262(10) -0.0002(8) -0.0013(8) -0.0040(8) C6 0.0152(12) 0.0204(10) 0.0244(10) -0.0031(8) -0.0005(8) -0.0027(8) C7 0.0183(12) 0.0228(10) 0.0189(9) -0.0027(7) -0.0027(8) -0.0020(8) C17 0.0156(12) 0.0207(9) 0.0245(9) 0.0016(7) -0.0048(8) -0.0033(8) C12 0.0164(12) 0.0271(10) 0.0262(10) 0.0022(8) -0.0014(9) -0.0038(8) C13 0.0246(14) 0.0306(11) 0.0322(11) 0.0085(9) -0.0047(9) -0.0046(10) C14 0.0245(14) 0.0235(10) 0.0448(13) 0.0074(9) -0.0076(10) -0.0023(9) C15 0.0210(13) 0.0216(9) 0.0403(12) -0.0055(9) -0.0035(9) -0.0009(8) C16 0.0205(13) 0.0229(10) 0.0281(10) -0.0034(8) -0.0041(8) -0.0020(8) C1 0.0122(12) 0.0244(10) 0.0252(10) -0.0034(8) -0.0020(8) 0.0010(8) C2 0.0157(13) 0.0291(11) 0.0329(10) -0.0111(9) 0.0000(9) 0.0025(9) C3 0.0192(13) 0.0199(9) 0.0472(13) -0.0061(9) -0.0034(10) 0.0011(8) C9 0.0206(13) 0.0371(12) 0.0209(10) -0.0094(9) 0.0007(9) 0.0075(9) C10 0.0253(14) 0.0415(13) 0.0184(9) -0.0017(9) -0.0008(9) 0.0060(10) C11 0.0201(13) 0.0336(11) 0.0206(10) 0.0043(8) 0.0029(9) 0.0022(9) C8 0.0158(12) 0.0263(10) 0.0197(9) -0.0013(8) 0.0011(8) -0.0008(8) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C7 N1 C17 127.97(18) C7 N1 C8 121.67(17) C17 N1 C8 109.26(16) C9 N2 C1 124.41(18) C9 N2 C8 113.70(17) C1 N2 C8 115.84(16) C5 C4 C3 119.8(2) C5 C4 H4 120.1 C3 C4 H4 120.1 C4 C5 C6 120.6(2) C4 C5 H5 119.7 C6 C5 H5 119.7 C5 C6 C1 118.94(19) C5 C6 C7 119.67(18) C1 C6 C7 121.08(18) O1 C7 N1 123.04(19) O1 C7 C6 122.34(19) N1 C7 C6 114.50(17) C16 C17 C12 122.00(19) C16 C17 N1 128.43(18) C12 C17 N1 109.56(18) C13 C12 C17 119.7(2) C13 C12 C11 129.6(2) C17 C12 C11 110.71(18) C12 C13 C14 119.2(2) C12 C13 H13 120.4 C14 C13 H13 120.4 C15 C14 C13 120.5(2) C15 C14 H14 119.7 C13 C14 H14 119.7 C14 C15 C16 121.1(2) C14 C15 H16 119.5 C16 C15 H16 119.5 C17 C16 C15 117.5(2) C17 C16 H15 121.2 C15 C16 H15 121.2 C2 C1 C6 120.7(2) C2 C1 N2 121.87(19) C6 C1 N2 117.35(17) C3 C2 C1 119.2(2) C3 C2 H2 120.4 C1 C2 H2 120.4 C2 C3 C4 120.78(19) C2 C3 H3 119.6 C4 C3 H3 119.6 O2 C9 N2 124.2(2) O2 C9 C10 127.8(2) N2 C9 C10 107.92(19) C9 C10 C11 106.46(17) C9 C10 H10B 110.4 C11 C10 H10B 110.4 C9 C10 H10A 110.4 C11 C10 H10A 110.4 H10B C10 H10A 108.6 C12 C11 C8 102.62(16) C12 C11 C10 115.9(2) C8 C11 C10 104.62(17) C12 C11 H11 111.1 C8 C11 H11 111.1 C10 C11 H11 111.1 N2 C8 N1 110.21(17) N2 C8 C11 106.34(17) N1 C8 C11 105.67(17) N2 C8 H8 111.4 N1 C8 H8 111.4 C11 C8 H8 111.4 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O2 C9 1.208(3) O1 C7 1.227(3) N1 C7 1.364(3) N1 C17 1.413(3) N1 C8 1.479(3) N2 C9 1.390(3) N2 C1 1.416(3) N2 C8 1.440(3) C4 C5 1.384(3) C4 C3 1.392(3) C4 H4 0.9500 C5 C6 1.390(3) C5 H5 0.9500 C6 C1 1.403(3) C6 C7 1.495(3) C17 C16 1.387(3) C17 C12 1.398(3) C12 C13 1.383(3) C12 C11 1.513(3) C13 C14 1.391(4) C13 H13 0.9500 C14 C15 1.391(3) C14 H14 0.9500 C15 C16 1.395(3) C15 H16 0.9500 C16 H15 0.9500 C1 C2 1.392(3) C2 C3 1.384(3) C2 H2 0.9500 C3 H3 0.9500 C9 C10 1.516(3) C10 C11 1.548(3) C10 H10B 0.9900 C10 H10A 0.9900 C11 C8 1.542(3) C11 H11 1.0000 C8 H8 1.0000 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 C16 H15 O1 0.95 2.49 3.001(3) 113.6 . C11 H11 O1 1.00 2.42 3.224(3) 137.5 4_664 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 C3 C4 C5 C6 0.9(4) C4 C5 C6 C1 -1.2(4) C4 C5 C6 C7 172.5(2) C17 N1 C7 O1 -16.3(3) C8 N1 C7 O1 177.0(2) C17 N1 C7 C6 159.78(19) C8 N1 C7 C6 -7.0(3) C5 C6 C7 O1 -14.0(3) C1 C6 C7 O1 159.6(2) C5 C6 C7 N1 169.9(2) C1 C6 C7 N1 -16.5(3) C7 N1 C17 C16 21.5(4) C8 N1 C17 C16 -170.4(2) C7 N1 C17 C12 -157.0(2) C8 N1 C17 C12 11.0(2) C16 C17 C12 C13 -1.4(3) N1 C17 C12 C13 177.3(2) C16 C17 C12 C11 179.2(2) N1 C17 C12 C11 -2.1(3) C17 C12 C13 C14 1.0(4) C11 C12 C13 C14 -179.7(2) C12 C13 C14 C15 0.4(4) C13 C14 C15 C16 -1.6(4) C12 C17 C16 C15 0.2(3) N1 C17 C16 C15 -178.2(2) C14 C15 C16 C17 1.2(3) C5 C6 C1 C2 1.5(3) C7 C6 C1 C2 -172.2(2) C5 C6 C1 N2 178.6(2) C7 C6 C1 N2 5.0(3) C9 N2 C1 C2 56.3(3) C8 N2 C1 C2 -152.9(2) C9 N2 C1 C6 -120.8(2) C8 N2 C1 C6 30.0(3) C6 C1 C2 C3 -1.3(4) N2 C1 C2 C3 -178.3(2) C1 C2 C3 C4 0.9(4) C5 C4 C3 C2 -0.7(4) C1 N2 C9 O2 -20.3(3) C8 N2 C9 O2 -171.6(2) C1 N2 C9 C10 158.74(19) C8 N2 C9 C10 7.4(3) O2 C9 C10 C11 177.8(2) N2 C9 C10 C11 -1.2(2) C13 C12 C11 C8 173.6(2) C17 C12 C11 C8 -7.1(2) C13 C12 C11 C10 -73.1(3) C17 C12 C11 C10 106.3(2) C9 C10 C11 C12 -116.9(2) C9 C10 C11 C8 -4.7(2) C9 N2 C8 N1 103.6(2) C1 N2 C8 N1 -50.3(2) C9 N2 C8 C11 -10.4(3) C1 N2 C8 C11 -164.35(17) C7 N1 C8 N2 39.3(3) C17 N1 C8 N2 -129.67(18) C7 N1 C8 C11 153.79(19) C17 N1 C8 C11 -15.2(2) C12 C11 C8 N2 130.18(18) C10 C11 C8 N2 8.8(2) C12 C11 C8 N1 13.0(2) C10 C11 C8 N1 -108.33(19)