#------------------------------------------------------------------------------ #$Date: 2025-03-25 04:27:59 +0200 (Tue, 25 Mar 2025) $ #$Revision: 298572 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/25/01/7250173.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_7250173 loop_ _publ_author_name 'Yang, Fang' 'Wang, Lin-Lin' 'Liu, Yu-Hua' 'Wu, Ke-Xin' 'Chen, Zi-Sheng' 'Ji, Kegong' _publ_section_title ; Br\/onsted acid-catalyzed two-component tandem condensation and cycloisomerization to 6(2H)-isoquinolinones ; _journal_issue 12 _journal_name_full 'RSC Advances' _journal_page_first 8913 _journal_page_last 8917 _journal_paper_doi 10.1039/D5RA01267H _journal_volume 15 _journal_year 2025 _chemical_formula_moiety 'C21 H15 N O' _chemical_formula_sum 'C21 H15 N O' _chemical_formula_weight 297.34 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-06-28 _audit_creation_method ; Olex2 1.3 (compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032) ; _audit_update_record ; 2021-05-04 deposited with the CCDC. 2025-03-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.5288(5) _cell_length_b 14.6591(5) _cell_length_c 16.0719(6) _cell_measurement_reflns_used 3385 _cell_measurement_temperature 100.0(2) _cell_measurement_theta_max 72.9680 _cell_measurement_theta_min 5.3820 _cell_volume 2951.78(19) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -33.00 62.00 1.00 1.50 -- 40.98 -38.00 60.00 95 2 \w 41.00 115.00 1.00 2.00 -- 106.95-125.00 90.00 74 3 \w 82.00 109.00 1.00 2.00 -- 106.95 -95.00 -60.00 27 4 \w 62.00 92.00 1.00 1.50 -- 40.98-125.00-120.00 30 5 \w 61.00 88.00 1.00 1.50 -- 40.98-125.00-180.00 27 6 \w 28.00 106.00 1.00 2.00 -- 106.95 -95.00-150.00 78 7 \w 78.00 178.00 1.00 2.00 -- 106.95 77.00-150.00 100 8 \w 123.00 169.00 1.00 2.00 -- 106.95 125.00 -90.00 46 9 \w 107.00 157.00 1.00 2.00 -- 106.95 123.00 23.00 50 10 \w 78.00 170.00 1.00 2.00 -- 106.95 61.00 120.00 92 11 \w -112.00 -16.00 1.00 1.50 -- -40.98 -38.00 -90.00 96 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1174549000 _diffrn_orient_matrix_UB_12 -0.0313976000 _diffrn_orient_matrix_UB_13 -0.0039118000 _diffrn_orient_matrix_UB_21 0.0354809000 _diffrn_orient_matrix_UB_22 -0.0913833000 _diffrn_orient_matrix_UB_23 -0.0382997000 _diffrn_orient_matrix_UB_31 0.0105311000 _diffrn_orient_matrix_UB_32 -0.0414261000 _diffrn_orient_matrix_UB_33 0.0875855000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0804 _diffrn_reflns_av_unetI/netI 0.0562 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.982 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 11528 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.982 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.833 _diffrn_reflns_theta_min 5.399 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.644 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.43508 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.338 _exptl_crystal_description block _exptl_crystal_F_000 1248 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.236 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 2934 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0591 _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^)+(0.0725P)^2^+1.6857P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1465 _refine_ls_wR_factor_ref 0.1607 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2299 _reflns_number_total 2934 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5ra01267h2.cif _cod_data_source_block 71-1 _cod_database_code 7250173 _shelx_shelxl_version_number 2018/3 _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_max 0.950 _shelx_estimated_absorpt_t_min 0.927 _reflns_odcompleteness_completeness 99.97 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C9(H9), C7(H7), C2(H2), C21(H21), C3(H3), C11(H11), C20(H20), C5(H5), C17(H17), C19(H19), C15(H15), C18(H18), C12(H12), C13(H13), C14(H14) ; _shelx_res_file ; TITL 71-1_a.res in Pbca 71-1.res created by SHELXL-2018/3 at 12:19:53 on 28-Jun-2020 REM Old TITL 71-1 in Pbca REM SHELXT solution in Pbca: R1 0.135, Rweak 0.127, Alpha 0.019 REM 0.471 for 384 systematic absences, Orientation as input REM Formula found by SHELXT: C21 N O CELL 1.54184 12.5288 14.6591 16.0719 90 90 90 ZERR 8 0.0005 0.0005 0.0006 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 168 120 8 8 L.S. 20 PLAN 5 SIZE 0.08 0.11 0.12 CONF BOND list 4 fmap 2 53 acta MORE -1 BOND $H OMIT 4 8 17 OMIT 2 7 18 REM REM REM WGHT 0.072500 1.685700 FVAR 0.37984 O1 4 0.796687 0.640020 0.514982 11.00000 0.01747 0.04161 = 0.03423 -0.00117 0.00071 -0.00077 N1 3 0.318414 0.564930 0.616247 11.00000 0.01913 0.02274 = 0.02357 0.00251 -0.00262 -0.00087 C8 1 0.379989 0.497682 0.654994 11.00000 0.02286 0.02076 = 0.02033 -0.00030 -0.00345 0.00148 C16 1 0.206296 0.580151 0.633388 11.00000 0.01825 0.01869 = 0.02633 0.00535 0.00104 -0.00027 C9 1 0.365504 0.625332 0.564223 11.00000 0.02114 0.02292 = 0.02627 0.00312 -0.00304 -0.00056 AFIX 43 H9 2 0.322799 0.668621 0.538125 11.00000 -1.20000 AFIX 0 C7 1 0.486938 0.495615 0.640241 11.00000 0.02232 0.02307 = 0.02429 0.00205 -0.00383 0.00444 AFIX 43 H7 2 0.527354 0.450351 0.665761 11.00000 -1.20000 AFIX 0 C6 1 0.540484 0.559848 0.587231 11.00000 0.02246 0.02327 = 0.02225 -0.00359 -0.00209 0.00151 C1 1 0.472238 0.625985 0.548120 11.00000 0.02121 0.02195 = 0.02379 -0.00078 -0.00181 -0.00113 C10 1 0.327596 0.432686 0.713364 11.00000 0.02653 0.02038 = 0.02350 0.00161 0.00063 0.00344 C4 1 0.697296 0.632009 0.523688 11.00000 0.01948 0.03040 = 0.02409 -0.00645 -0.00109 -0.00046 C2 1 0.518558 0.692577 0.494093 11.00000 0.02244 0.02538 = 0.02846 0.00175 -0.00195 -0.00018 AFIX 43 H2 2 0.475059 0.734903 0.467483 11.00000 -1.20000 AFIX 0 C21 1 0.132673 0.561984 0.571412 11.00000 0.02423 0.02431 = 0.02476 0.00036 -0.00039 -0.00170 AFIX 43 H21 2 0.153977 0.534347 0.522045 11.00000 -1.20000 AFIX 0 C3 1 0.624725 0.694384 0.481511 11.00000 0.02460 0.02516 = 0.02789 0.00076 0.00267 -0.00262 AFIX 43 H3 2 0.652757 0.736953 0.444589 11.00000 -1.20000 AFIX 0 C11 1 0.232695 0.387577 0.693972 11.00000 0.02454 0.02479 = 0.02737 0.00389 -0.00043 0.00215 AFIX 43 H11 2 0.199787 0.397426 0.642888 11.00000 -1.20000 AFIX 0 C20 1 0.026885 0.585497 0.583871 11.00000 0.02024 0.02544 = 0.03523 0.00275 -0.00407 -0.00190 AFIX 43 H20 2 -0.023574 0.572875 0.543023 11.00000 -1.20000 AFIX 0 C5 1 0.649206 0.563291 0.574690 11.00000 0.02068 0.02621 = 0.02706 -0.00160 -0.00360 0.00528 AFIX 43 H5 2 0.692467 0.519852 0.600012 11.00000 -1.20000 AFIX 0 C17 1 0.176692 0.621521 0.706921 11.00000 0.02495 0.02616 = 0.02474 0.00348 -0.00255 0.00015 AFIX 43 H17 2 0.227123 0.633151 0.748035 11.00000 -1.20000 AFIX 0 C19 1 -0.003980 0.627854 0.657187 11.00000 0.02000 0.02776 = 0.03836 0.00995 0.00558 0.00316 AFIX 43 H19 2 -0.074924 0.644408 0.665050 11.00000 -1.20000 AFIX 0 C15 1 0.377987 0.414490 0.788895 11.00000 0.03226 0.02374 = 0.02737 -0.00009 -0.00243 0.00089 AFIX 43 H15 2 0.442214 0.443068 0.801627 11.00000 -1.20000 AFIX 0 C18 1 0.070613 0.645566 0.718739 11.00000 0.03149 0.02737 = 0.03103 0.00214 0.00776 0.00402 AFIX 43 H18 2 0.049598 0.673583 0.768003 11.00000 -1.20000 AFIX 0 C12 1 0.187486 0.327890 0.751205 11.00000 0.02791 0.02625 = 0.03639 0.00161 0.00497 -0.00059 AFIX 43 H12 2 0.123680 0.298607 0.738515 11.00000 -1.20000 AFIX 0 C13 1 0.236868 0.311574 0.827319 11.00000 0.04103 0.02601 = 0.03103 0.00541 0.01232 0.00256 AFIX 43 H13 2 0.205616 0.272499 0.865849 11.00000 -1.20000 AFIX 0 C14 1 0.332818 0.353944 0.845209 11.00000 0.04469 0.02865 = 0.02287 0.00209 0.00029 0.00444 AFIX 43 H14 2 0.367265 0.341798 0.895254 11.00000 -1.20000 AFIX 0 HKLF 4 REM 71-1_a.res in Pbca REM wR2 = 0.1607, GooF = S = 1.023, Restrained GooF = 1.023 for all data REM R1 = 0.0591 for 2299 Fo > 4sig(Fo) and 0.0752 for all 2934 data REM 208 parameters refined using 0 restraints END WGHT 0.0801 1.0427 REM Highest difference peak 0.236, deepest hole -0.266, 1-sigma level 0.062 Q1 1 -0.0944 0.6390 0.6439 11.00000 0.05 0.24 Q2 1 0.5016 0.7649 0.5886 11.00000 0.05 0.20 Q3 1 0.2557 0.4398 0.7189 11.00000 0.05 0.20 Q4 1 0.1753 0.5010 0.5389 11.00000 0.05 0.20 Q5 1 0.7012 0.4974 0.7135 11.00000 0.05 0.20 ; _shelx_res_checksum 82211 _olex2_date_sample_data_collection 2020-06-28 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.801 _oxdiff_exptl_absorpt_empirical_full_min 0.207 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' '-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 0.79669(13) 0.64002(11) 0.51498(10) 0.0311(4) Uani 1 1 d . . . . . N1 N 0.31841(14) 0.56493(11) 0.61625(11) 0.0218(4) Uani 1 1 d . . . . . C8 C 0.37999(17) 0.49768(13) 0.65499(12) 0.0213(4) Uani 1 1 d . . . . . C16 C 0.20630(17) 0.58015(13) 0.63339(13) 0.0211(4) Uani 1 1 d . . . . . C9 C 0.36550(18) 0.62533(14) 0.56422(13) 0.0234(5) Uani 1 1 d . . . . . H9 H 0.322799 0.668621 0.538125 0.028 Uiso 1 1 calc R U . . . C7 C 0.48694(17) 0.49562(14) 0.64024(13) 0.0232(5) Uani 1 1 d . . . . . H7 H 0.527354 0.450351 0.665761 0.028 Uiso 1 1 calc R U . . . C6 C 0.54048(18) 0.55985(14) 0.58723(13) 0.0227(5) Uani 1 1 d . . . . . C1 C 0.47224(18) 0.62598(14) 0.54812(13) 0.0223(5) Uani 1 1 d . . . . . C10 C 0.32760(18) 0.43269(14) 0.71336(13) 0.0235(5) Uani 1 1 d . . . . . C4 C 0.69730(17) 0.63201(15) 0.52369(13) 0.0247(5) Uani 1 1 d . . . . . C2 C 0.51856(18) 0.69258(15) 0.49409(13) 0.0254(5) Uani 1 1 d . . . . . H2 H 0.475059 0.734903 0.467483 0.031 Uiso 1 1 calc R U . . . C21 C 0.13267(18) 0.56198(14) 0.57141(13) 0.0244(5) Uani 1 1 d . . . . . H21 H 0.153977 0.534347 0.522045 0.029 Uiso 1 1 calc R U . . . C3 C 0.62472(18) 0.69438(15) 0.48151(14) 0.0259(5) Uani 1 1 d . . . . . H3 H 0.652757 0.736953 0.444589 0.031 Uiso 1 1 calc R U . . . C11 C 0.23269(18) 0.38758(14) 0.69397(14) 0.0256(5) Uani 1 1 d . . . . . H11 H 0.199787 0.397426 0.642888 0.031 Uiso 1 1 calc R U . . . C20 C 0.02688(18) 0.58550(14) 0.58387(14) 0.0270(5) Uani 1 1 d . . . . . H20 H -0.023574 0.572875 0.543023 0.032 Uiso 1 1 calc R U . . . C5 C 0.64921(17) 0.56329(14) 0.57469(13) 0.0246(5) Uani 1 1 d . . . . . H5 H 0.692467 0.519852 0.600012 0.030 Uiso 1 1 calc R U . . . C17 C 0.17669(18) 0.62152(14) 0.70692(13) 0.0253(5) Uani 1 1 d . . . . . H17 H 0.227123 0.633151 0.748035 0.030 Uiso 1 1 calc R U . . . C19 C -0.00398(19) 0.62785(15) 0.65719(15) 0.0287(5) Uani 1 1 d . . . . . H19 H -0.074924 0.644408 0.665050 0.034 Uiso 1 1 calc R U . . . C15 C 0.3780(2) 0.41449(15) 0.78889(14) 0.0278(5) Uani 1 1 d . . . . . H15 H 0.442214 0.443068 0.801627 0.033 Uiso 1 1 calc R U . . . C18 C 0.0706(2) 0.64557(15) 0.71874(15) 0.0300(5) Uani 1 1 d . . . . . H18 H 0.049598 0.673583 0.768003 0.036 Uiso 1 1 calc R U . . . C12 C 0.18749(19) 0.32789(15) 0.75121(15) 0.0302(5) Uani 1 1 d . . . . . H12 H 0.123680 0.298607 0.738515 0.036 Uiso 1 1 calc R U . . . C13 C 0.2369(2) 0.31157(16) 0.82732(15) 0.0327(6) Uani 1 1 d . . . . . H13 H 0.205616 0.272499 0.865849 0.039 Uiso 1 1 calc R U . . . C14 C 0.3328(2) 0.35394(16) 0.84521(14) 0.0321(5) Uani 1 1 d . . . . . H14 H 0.367265 0.341798 0.895254 0.038 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 0.0175(8) 0.0416(9) 0.0342(9) -0.0012(7) 0.0007(7) -0.0008(7) N1 0.0191(9) 0.0227(8) 0.0236(9) 0.0025(7) -0.0026(7) -0.0009(7) C8 0.0229(10) 0.0208(10) 0.0203(10) -0.0003(8) -0.0035(8) 0.0015(8) C16 0.0183(10) 0.0187(9) 0.0263(11) 0.0053(8) 0.0010(8) -0.0003(8) C9 0.0211(11) 0.0229(10) 0.0263(11) 0.0031(8) -0.0030(9) -0.0006(8) C7 0.0223(11) 0.0231(10) 0.0243(10) 0.0020(8) -0.0038(8) 0.0044(8) C6 0.0225(11) 0.0233(10) 0.0223(10) -0.0036(8) -0.0021(8) 0.0015(8) C1 0.0212(11) 0.0219(10) 0.0238(10) -0.0008(8) -0.0018(8) -0.0011(8) C10 0.0265(12) 0.0204(9) 0.0235(10) 0.0016(8) 0.0006(9) 0.0034(9) C4 0.0195(11) 0.0304(11) 0.0241(11) -0.0064(8) -0.0011(9) -0.0005(9) C2 0.0224(11) 0.0254(10) 0.0285(11) 0.0018(8) -0.0019(9) -0.0002(9) C21 0.0242(11) 0.0243(10) 0.0248(11) 0.0004(8) -0.0004(9) -0.0017(9) C3 0.0246(11) 0.0252(10) 0.0279(11) 0.0008(8) 0.0027(9) -0.0026(9) C11 0.0245(11) 0.0248(10) 0.0274(11) 0.0039(8) -0.0004(9) 0.0022(9) C20 0.0202(11) 0.0254(10) 0.0352(12) 0.0028(9) -0.0041(9) -0.0019(9) C5 0.0207(11) 0.0262(10) 0.0271(11) -0.0016(8) -0.0036(9) 0.0053(9) C17 0.0250(12) 0.0262(10) 0.0247(11) 0.0035(8) -0.0026(9) 0.0002(9) C19 0.0200(10) 0.0278(11) 0.0384(12) 0.0099(9) 0.0056(10) 0.0032(9) C15 0.0323(13) 0.0237(10) 0.0274(11) -0.0001(8) -0.0024(10) 0.0009(9) C18 0.0315(13) 0.0274(11) 0.0310(11) 0.0021(9) 0.0078(10) 0.0040(10) C12 0.0279(12) 0.0263(11) 0.0364(12) 0.0016(9) 0.0050(10) -0.0006(9) C13 0.0410(14) 0.0260(11) 0.0310(12) 0.0054(9) 0.0123(11) 0.0026(10) C14 0.0447(15) 0.0287(11) 0.0229(11) 0.0021(9) 0.0003(10) 0.0044(11) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C16 123.98(17) . . ? C9 N1 C8 119.74(19) . . ? C9 N1 C16 116.07(17) . . ? N1 C8 C10 119.23(19) . . ? C7 C8 N1 118.77(19) . . ? C7 C8 C10 121.96(19) . . ? C21 C16 N1 118.68(19) . . ? C17 C16 N1 119.43(19) . . ? C17 C16 C21 121.5(2) . . ? N1 C9 H9 118.3 . . ? N1 C9 C1 123.4(2) . . ? C1 C9 H9 118.3 . . ? C8 C7 H7 118.4 . . ? C8 C7 C6 123.27(19) . . ? C6 C7 H7 118.4 . . ? C7 C6 C1 115.1(2) . . ? C5 C6 C7 124.9(2) . . ? C5 C6 C1 120.0(2) . . ? C9 C1 C6 119.7(2) . . ? C9 C1 C2 121.2(2) . . ? C2 C1 C6 119.0(2) . . ? C11 C10 C8 122.54(19) . . ? C15 C10 C8 118.1(2) . . ? C15 C10 C11 119.3(2) . . ? O1 C4 C3 120.5(2) . . ? O1 C4 C5 123.1(2) . . ? C5 C4 C3 116.4(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 C1 120.4(2) . . ? C3 C2 H2 119.8 . . ? C16 C21 H21 120.4 . . ? C16 C21 C20 119.1(2) . . ? C20 C21 H21 120.4 . . ? C4 C3 H3 118.8 . . ? C2 C3 C4 122.3(2) . . ? C2 C3 H3 118.8 . . ? C10 C11 H11 120.1 . . ? C12 C11 C10 119.8(2) . . ? C12 C11 H11 120.1 . . ? C21 C20 H20 120.0 . . ? C21 C20 C19 120.1(2) . . ? C19 C20 H20 120.0 . . ? C6 C5 C4 121.7(2) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C16 C17 H17 120.4 . . ? C16 C17 C18 119.1(2) . . ? C18 C17 H17 120.4 . . ? C20 C19 H19 119.9 . . ? C18 C19 C20 120.2(2) . . ? C18 C19 H19 119.9 . . ? C10 C15 H15 119.8 . . ? C14 C15 C10 120.4(2) . . ? C14 C15 H15 119.8 . . ? C17 C18 H18 120.0 . . ? C19 C18 C17 120.0(2) . . ? C19 C18 H18 120.0 . . ? C11 C12 H12 119.7 . . ? C11 C12 C13 120.6(2) . . ? C13 C12 H12 119.7 . . ? C12 C13 H13 120.3 . . ? C14 C13 C12 119.5(2) . . ? C14 C13 H13 120.3 . . ? C15 C14 H14 119.8 . . ? C13 C14 C15 120.4(2) . . ? C13 C14 H14 119.8 . . ? 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 C4 1.259(3) . ? N1 C8 1.398(3) . ? N1 C16 1.449(3) . ? N1 C9 1.353(3) . ? C8 C7 1.361(3) . ? C8 C10 1.490(3) . ? C16 C21 1.383(3) . ? C16 C17 1.379(3) . ? C9 H9 0.9300 . ? C9 C1 1.362(3) . ? C7 H7 0.9300 . ? C7 C6 1.436(3) . ? C6 C1 1.437(3) . ? C6 C5 1.378(3) . ? C1 C2 1.430(3) . ? C10 C11 1.396(3) . ? C10 C15 1.394(3) . ? C4 C3 1.457(3) . ? C4 C5 1.432(3) . ? C2 H2 0.9300 . ? C2 C3 1.346(3) . ? C21 H21 0.9300 . ? C21 C20 1.384(3) . ? C3 H3 0.9300 . ? C11 H11 0.9300 . ? C11 C12 1.390(3) . ? C20 H20 0.9300 . ? C20 C19 1.387(3) . ? C5 H5 0.9300 . ? C17 H17 0.9300 . ? C17 C18 1.388(3) . ? C19 H19 0.9300 . ? C19 C18 1.385(3) . ? C15 H15 0.9300 . ? C15 C14 1.388(3) . ? C18 H18 0.9300 . ? C12 H12 0.9300 . ? C12 C13 1.392(4) . ? C13 H13 0.9300 . ? C13 C14 1.383(4) . ? C14 H14 0.9300 . ? 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 O1 C4 C3 C2 -174.8(2) . . . . ? O1 C4 C5 C6 175.8(2) . . . . ? N1 C8 C7 C6 0.6(3) . . . . ? N1 C8 C10 C11 47.4(3) . . . . ? N1 C8 C10 C15 -134.8(2) . . . . ? N1 C16 C21 C20 -173.07(18) . . . . ? N1 C16 C17 C18 172.52(18) . . . . ? N1 C9 C1 C6 0.2(3) . . . . ? N1 C9 C1 C2 -178.55(19) . . . . ? C8 N1 C16 C21 -113.0(2) . . . . ? C8 N1 C16 C17 74.1(3) . . . . ? C8 N1 C9 C1 -1.4(3) . . . . ? C8 C7 C6 C1 -1.8(3) . . . . ? C8 C7 C6 C5 175.9(2) . . . . ? C8 C10 C11 C12 -179.8(2) . . . . ? C8 C10 C15 C14 -179.6(2) . . . . ? C16 N1 C8 C7 -173.42(19) . . . . ? C16 N1 C8 C10 4.4(3) . . . . ? C16 N1 C9 C1 173.4(2) . . . . ? C16 C21 C20 C19 0.9(3) . . . . ? C16 C17 C18 C19 0.1(3) . . . . ? C9 N1 C8 C7 1.0(3) . . . . ? C9 N1 C8 C10 178.86(18) . . . . ? C9 N1 C16 C21 72.3(2) . . . . ? C9 N1 C16 C17 -100.5(2) . . . . ? C9 C1 C2 C3 177.4(2) . . . . ? C7 C8 C10 C11 -134.9(2) . . . . ? C7 C8 C10 C15 42.9(3) . . . . ? C7 C6 C1 C9 1.4(3) . . . . ? C7 C6 C1 C2 -179.87(19) . . . . ? C7 C6 C5 C4 -177.2(2) . . . . ? C6 C1 C2 C3 -1.4(3) . . . . ? C1 C6 C5 C4 0.5(3) . . . . ? C1 C2 C3 C4 -2.2(3) . . . . ? C10 C8 C7 C6 -177.14(19) . . . . ? C10 C11 C12 C13 -1.0(3) . . . . ? C10 C15 C14 C13 -0.5(3) . . . . ? C21 C16 C17 C18 -0.1(3) . . . . ? C21 C20 C19 C18 -1.0(3) . . . . ? C3 C4 C5 C6 -3.8(3) . . . . ? C11 C10 C15 C14 -1.7(3) . . . . ? C11 C12 C13 C14 -1.3(3) . . . . ? C20 C19 C18 C17 0.5(3) . . . . ? C5 C6 C1 C9 -176.5(2) . . . . ? C5 C6 C1 C2 2.3(3) . . . . ? C5 C4 C3 C2 4.8(3) . . . . ? C17 C16 C21 C20 -0.4(3) . . . . ? C15 C10 C11 C12 2.4(3) . . . . ? C12 C13 C14 C15 2.0(4) . . . . ?