#------------------------------------------------------------------------------ #$Date: 2026-06-23 22:42:49 +0100 (Tue, 23 Jun 2026) $ #$Revision: 306617 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577424.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_1577424 loop_ _publ_author_name 'Zameer, Nazia' 'Mustafa, Atif' 'Siddiqui, Zeba N.' _publ_section_title ; Phosphotungstic acid-doped covalent triazine framework as a bifunctional heterogeneous catalyst for one-pot multicomponent synthesis of spiro-quinazolinones under green reaction conditions ; _journal_name_full 'Catalysis Science & Technology' _journal_paper_doi 10.1039/D6CY00252H _journal_year 2026 _chemical_formula_sum 'C26 H23 Cl N4 O5' _chemical_formula_weight 506.93 _chemical_name_systematic N-(5-chloro-2,4'-dioxo-1',4'-dihydro-3'H-spiro[indoline-3,2'-quinazolin]-3'-yl)benzamide _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2026-02-05 deposited with the CCDC. 2026-06-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.756(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.1522(3) _cell_length_b 21.2157(7) _cell_length_c 8.3685(2) _cell_measurement_reflns_used 17596 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.1280 _cell_measurement_theta_min 2.3980 _cell_volume 2499.96(12) _computing_cell_refinement 'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.954 _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix3000' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_unetI/netI 0.0258 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.954 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 37349 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.954 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.400 _diffrn_reflns_theta_min 1.736 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.85739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.347 _exptl_crystal_description block _exptl_crystal_F_000 1056 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ethyl acetate and hexane' _refine_diff_density_max 0.510 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 327 _refine_ls_number_reflns 5426 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.080 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0523 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+0.6594P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1394 _refine_ls_wR_factor_ref 0.1529 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3833 _reflns_number_total 5426 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6cy00252h32.cif _cod_data_source_block ia13 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1577424 _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_res_file ; TITL ia13_a.res in P2(1)/c ia13.res created by SHELXL-2018/3 at 13:44:53 on 29-Jan-2026 REM Old TITL ia13_a.res in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.166, Rweak 0.012, Alpha 0.025 REM 0.646 for 156 systematic absences, Orientation as input REM Formula found by SHELXT: C27 Cl N4 O4 CELL 0.71073 14.1522 21.2157 8.3685 90 95.756 90 ZERR 4 0.0003 0.0007 0.0002 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N O UNIT 104 92 4 16 20 L.S. 4 PLAN 20 CONF BOND list 4 fmap 2 acta MORE -1 BOND $H REM REM REM WGHT 0.071700 0.659400 FVAR 0.53019 CL01 3 0.493847 0.596665 0.410000 11.00000 0.05047 0.07886 = 0.07474 0.00603 0.00961 -0.01578 O002 5 0.303115 0.572966 0.819710 11.00000 0.04560 0.06331 = 0.04537 -0.00104 -0.00351 0.00176 O003 5 0.083756 0.504585 0.902117 11.00000 0.04798 0.06720 = 0.04218 -0.00648 0.01188 0.00239 O004 5 0.031876 0.425138 0.444448 11.00000 0.04253 0.06972 = 0.06354 0.00459 -0.00510 -0.01148 N005 4 0.160481 0.567184 0.673918 11.00000 0.04062 0.04225 = 0.04223 -0.00138 -0.00051 0.00129 AFIX 43 H005 2 0.116815 0.586897 0.614887 11.00000 -1.20000 AFIX 0 N006 4 0.162845 0.501994 0.680468 11.00000 0.04396 0.04365 = 0.03758 -0.00290 0.00739 -0.00111 N007 4 0.232559 0.408661 0.596577 11.00000 0.03897 0.05030 = 0.04610 0.00473 0.00837 0.00806 AFIX 43 H007 2 0.284338 0.395557 0.562150 11.00000 -1.20000 AFIX 0 N008 4 0.114963 0.486603 0.281106 11.00000 0.04574 0.06227 = 0.03673 -0.00220 -0.00620 -0.00163 AFIX 43 H008 2 0.074521 0.487770 0.197295 11.00000 -1.20000 AFIX 0 O009 5 0.336724 0.329717 0.381649 11.00000 0.07928 0.09390 = 0.10878 -0.03708 0.04329 -0.01248 C00A 1 0.252468 0.505461 0.442443 11.00000 0.03965 0.04647 = 0.03263 -0.00411 0.00497 0.00269 C00B 1 0.230639 0.598896 0.765444 11.00000 0.04122 0.05311 = 0.03004 0.00113 0.00586 -0.00416 O00C 5 0.422245 0.341465 0.177725 11.00000 0.13021 0.07635 = 0.07165 0.00517 0.04113 0.03242 C00D 1 0.121156 0.473154 0.802546 11.00000 0.03272 0.05571 = 0.03600 -0.00088 0.00144 -0.00212 C00E 1 0.190412 0.467383 0.540359 11.00000 0.03505 0.04854 = 0.03351 -0.00226 0.00252 0.00258 C00F 1 0.204235 0.516168 0.291838 11.00000 0.04423 0.05021 = 0.03509 -0.00479 0.00103 0.00263 C00G 1 0.188317 0.373778 0.706769 11.00000 0.04222 0.05094 = 0.04225 0.00231 -0.00148 0.00107 C00H 1 0.130432 0.404572 0.808682 11.00000 0.04063 0.05465 = 0.03976 0.00268 0.00227 -0.00305 C00I 1 0.342431 0.529407 0.481028 11.00000 0.03829 0.05168 = 0.03738 -0.00121 0.00320 0.00251 AFIX 43 H00I 2 0.375479 0.522275 0.581138 11.00000 -1.20000 AFIX 0 C00J 1 0.100354 0.456300 0.417422 11.00000 0.03946 0.04806 = 0.04289 -0.00636 0.00038 0.00283 C00K 1 0.381596 0.564508 0.364702 11.00000 0.04370 0.05056 = 0.04793 -0.00162 0.00882 -0.00121 C00L 1 0.213830 0.667416 0.790656 11.00000 0.05459 0.04915 = 0.03899 0.00164 0.00798 -0.00723 C00M 1 0.333825 0.574663 0.214871 11.00000 0.06254 0.05840 = 0.04348 0.00555 0.01408 -0.00452 AFIX 43 H00M 2 0.362729 0.597798 0.138873 11.00000 -1.20000 AFIX 0 C00N 1 0.243921 0.550930 0.176757 11.00000 0.06402 0.06395 = 0.03461 0.00413 0.00094 -0.00068 AFIX 43 H00N 2 0.211037 0.558133 0.076548 11.00000 -1.20000 AFIX 0 C00O 1 0.203267 0.309129 0.724754 11.00000 0.06106 0.05302 = 0.06016 0.00698 0.00435 0.00915 AFIX 43 H00O 2 0.242590 0.288001 0.659987 11.00000 -1.20000 AFIX 0 C00P 1 0.086369 0.370210 0.921923 11.00000 0.06228 0.06828 = 0.05096 0.00863 0.01242 -0.00513 AFIX 43 H00P 2 0.047089 0.390691 0.987966 11.00000 -1.20000 AFIX 0 C00Q 1 0.397486 0.311316 0.303666 11.00000 0.06826 0.06856 = 0.05764 -0.01526 0.01566 -0.00806 C00R 1 0.159163 0.276747 0.839597 11.00000 0.08481 0.05205 = 0.07845 0.01781 0.00163 0.00222 AFIX 43 H00R 2 0.169485 0.233636 0.851493 11.00000 -1.20000 AFIX 0 C00S 1 0.292212 0.703862 0.840039 11.00000 0.06616 0.05716 = 0.08922 0.00014 0.00204 -0.01322 AFIX 43 H00S 2 0.352287 0.685657 0.851774 11.00000 -1.20000 AFIX 0 C00T 1 0.125257 0.695102 0.775867 11.00000 0.06556 0.05479 = 0.08784 -0.00750 0.00981 -0.00149 AFIX 43 H00T 2 0.071675 0.671214 0.743242 11.00000 -1.20000 AFIX 0 C00U 1 0.100290 0.306600 0.937003 11.00000 0.08117 0.07015 = 0.07229 0.02475 0.01826 -0.00382 AFIX 43 H00U 2 0.070311 0.283757 1.012242 11.00000 -1.20000 AFIX 0 C00V 1 0.452587 0.253013 0.334919 11.00000 0.10753 0.07595 = 0.07953 0.00797 0.02546 0.00850 AFIX 137 H00A 2 0.519072 0.262944 0.349586 11.00000 -1.50000 H00B 2 0.440399 0.224880 0.245374 11.00000 -1.50000 H00C 2 0.434236 0.233180 0.430184 11.00000 -1.50000 AFIX 0 C00W 1 0.194815 0.794169 0.855076 11.00000 0.11728 0.04701 = 0.09388 -0.00694 0.02024 -0.01013 AFIX 43 H00W 2 0.188582 0.837064 0.874374 11.00000 -1.20000 AFIX 0 C00X 1 0.281880 0.766997 0.871979 11.00000 0.09930 0.05564 = 0.12537 -0.00619 -0.00406 -0.02289 AFIX 43 H00X 2 0.335035 0.791170 0.905396 11.00000 -1.20000 AFIX 0 C00Y 1 0.116285 0.758691 0.809788 11.00000 0.08787 0.06309 = 0.10600 -0.00679 0.01904 0.01468 AFIX 43 H00Y 2 0.056445 0.777228 0.801617 11.00000 -1.20000 AFIX 0 C00Z 1 0.370506 0.399663 0.134482 11.00000 0.17415 0.08681 = 0.10380 0.01098 0.03934 0.05663 AFIX 23 H00D 2 0.303218 0.390706 0.113011 11.00000 -1.20000 H00E 2 0.379013 0.429333 0.222944 11.00000 -1.20000 AFIX 0 C010 1 0.404315 0.425776 -0.001298 11.00000 0.19985 0.09870 = 0.10093 0.01999 0.03554 0.04822 AFIX 137 H01A 2 0.394573 0.396595 -0.089077 11.00000 -1.50000 H01B 2 0.470909 0.434543 0.020510 11.00000 -1.50000 H01C 2 0.370791 0.464208 -0.029006 11.00000 -1.50000 AFIX 0 HKLF 4 REM ia13_a.res in P2(1)/c REM wR2 = 0.1529, GooF = S = 1.080, Restrained GooF = 1.080 for all data REM R1 = 0.0523 for 3833 Fo > 4sig(Fo) and 0.0748 for all 5426 data REM 327 parameters refined using 0 restraints END WGHT 0.0710 0.6743 REM Highest difference peak 0.510, deepest hole -0.366, 1-sigma level 0.046 Q1 1 0.4479 0.4144 0.1546 11.00000 0.05 0.51 Q2 1 0.2516 0.3825 0.5160 11.00000 0.05 0.36 Q3 1 0.0949 0.5810 0.6780 11.00000 0.05 0.34 Q4 1 0.4855 0.3512 0.2007 11.00000 0.05 0.29 Q5 1 0.3569 0.4071 0.0315 11.00000 0.05 0.18 Q6 1 0.1467 0.4570 0.4827 11.00000 0.05 0.17 Q7 1 0.2346 0.5129 0.3666 11.00000 0.05 0.16 Q8 1 0.5048 0.2384 0.2513 11.00000 0.05 0.16 Q9 1 0.2509 0.7783 0.7665 11.00000 0.05 0.15 Q10 1 0.1293 0.7603 0.7205 11.00000 0.05 0.14 Q11 1 0.0603 0.7895 0.6972 11.00000 0.05 0.14 Q12 1 0.1535 0.3865 0.7489 11.00000 0.05 0.14 Q13 1 -0.0144 0.6922 0.7996 11.00000 0.05 0.14 Q14 1 0.4814 0.2638 0.4923 11.00000 0.05 0.13 Q15 1 0.3570 0.3619 0.3191 11.00000 0.05 0.13 Q16 1 0.2174 0.6413 0.8149 11.00000 0.05 0.13 Q17 1 0.1041 0.4325 0.7885 11.00000 0.05 0.13 Q18 1 0.4501 0.6516 0.8109 11.00000 0.05 0.13 Q19 1 0.1844 0.3365 0.6990 11.00000 0.05 0.13 Q20 1 0.2299 0.4828 0.4903 11.00000 0.05 0.12 ; _shelx_res_checksum 58377 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl01 Cl 0.49385(4) 0.59667(3) 0.41000(8) 0.0678(2) Uani 1 1 d . . . . . O002 O 0.30311(10) 0.57297(7) 0.81971(17) 0.0520(4) Uani 1 1 d . . . . . O003 O 0.08376(10) 0.50458(7) 0.90212(16) 0.0520(4) Uani 1 1 d . . . . . O004 O 0.03188(10) 0.42514(8) 0.44445(19) 0.0593(4) Uani 1 1 d . . . . . N005 N 0.16048(11) 0.56718(8) 0.67392(19) 0.0420(4) Uani 1 1 d . . . . . H005 H 0.116815 0.586897 0.614887 0.050 Uiso 1 1 calc R U . . . N006 N 0.16284(11) 0.50199(8) 0.68047(18) 0.0415(4) Uani 1 1 d . . . . . N007 N 0.23256(11) 0.40866(8) 0.59658(19) 0.0448(4) Uani 1 1 d . . . . . H007 H 0.284338 0.395557 0.562150 0.054 Uiso 1 1 calc R U . . . N008 N 0.11496(12) 0.48660(9) 0.28111(19) 0.0489(4) Uani 1 1 d . . . . . H008 H 0.074521 0.487770 0.197295 0.059 Uiso 1 1 calc R U . . . O009 O 0.33672(14) 0.32972(10) 0.3816(3) 0.0917(7) Uani 1 1 d . . . . . C00A C 0.25247(13) 0.50546(9) 0.4424(2) 0.0395(4) Uani 1 1 d . . . . . C00B C 0.23064(14) 0.59890(10) 0.7654(2) 0.0413(4) Uani 1 1 d . . . . . O00C O 0.42225(17) 0.34146(9) 0.1777(2) 0.0906(6) Uani 1 1 d . . . . . C00D C 0.12116(13) 0.47315(10) 0.8025(2) 0.0416(5) Uani 1 1 d . . . . . C00E C 0.19041(13) 0.46738(9) 0.5404(2) 0.0391(4) Uani 1 1 d . . . . . C00F C 0.20424(14) 0.51617(10) 0.2918(2) 0.0434(5) Uani 1 1 d . . . . . C00G C 0.18832(14) 0.37378(10) 0.7068(2) 0.0455(5) Uani 1 1 d . . . . . C00H C 0.13043(14) 0.40457(10) 0.8087(2) 0.0451(5) Uani 1 1 d . . . . . C00I C 0.34243(13) 0.52941(10) 0.4810(2) 0.0425(5) Uani 1 1 d . . . . . H00I H 0.375479 0.522275 0.581138 0.051 Uiso 1 1 calc R U . . . C00J C 0.10035(14) 0.45630(10) 0.4174(2) 0.0437(5) Uani 1 1 d . . . . . C00K C 0.38160(14) 0.56451(10) 0.3647(2) 0.0471(5) Uani 1 1 d . . . . . C00L C 0.21383(15) 0.66742(10) 0.7907(2) 0.0474(5) Uani 1 1 d . . . . . C00M C 0.33383(17) 0.57466(11) 0.2149(3) 0.0542(5) Uani 1 1 d . . . . . H00M H 0.362729 0.597798 0.138873 0.065 Uiso 1 1 calc R U . . . C00N C 0.24392(17) 0.55093(11) 0.1768(2) 0.0545(5) Uani 1 1 d . . . . . H00N H 0.211037 0.558133 0.076548 0.065 Uiso 1 1 calc R U . . . C00O C 0.20327(17) 0.30913(11) 0.7248(3) 0.0582(6) Uani 1 1 d . . . . . H00O H 0.242590 0.288001 0.659987 0.070 Uiso 1 1 calc R U . . . C00P C 0.08637(17) 0.37021(12) 0.9219(3) 0.0601(6) Uani 1 1 d . . . . . H00P H 0.047089 0.390691 0.987966 0.072 Uiso 1 1 calc R U . . . C00Q C 0.39749(18) 0.31132(13) 0.3037(3) 0.0642(6) Uani 1 1 d . . . . . C00R C 0.1592(2) 0.27675(13) 0.8396(3) 0.0722(7) Uani 1 1 d . . . . . H00R H 0.169485 0.233636 0.851493 0.087 Uiso 1 1 calc R U . . . C00S C 0.29221(19) 0.70386(13) 0.8400(3) 0.0712(7) Uani 1 1 d . . . . . H00S H 0.352287 0.685657 0.851774 0.085 Uiso 1 1 calc R U . . . C00T C 0.12526(19) 0.69510(12) 0.7759(3) 0.0693(7) Uani 1 1 d . . . . . H00T H 0.071675 0.671214 0.743242 0.083 Uiso 1 1 calc R U . . . C00U C 0.1003(2) 0.30660(14) 0.9370(3) 0.0738(7) Uani 1 1 d . . . . . H00U H 0.070311 0.283757 1.012242 0.089 Uiso 1 1 calc R U . . . C00V C 0.4526(2) 0.25301(14) 0.3349(4) 0.0866(9) Uani 1 1 d . . . . . H00A H 0.519072 0.262944 0.349586 0.130 Uiso 1 1 calc R U . . . H00B H 0.440399 0.224880 0.245374 0.130 Uiso 1 1 calc R U . . . H00C H 0.434236 0.233180 0.430184 0.130 Uiso 1 1 calc R U . . . C00W C 0.1948(3) 0.79417(14) 0.8551(4) 0.0854(9) Uani 1 1 d . . . . . H00W H 0.188582 0.837064 0.874374 0.102 Uiso 1 1 calc R U . . . C00X C 0.2819(3) 0.76700(14) 0.8720(4) 0.0945(10) Uani 1 1 d . . . . . H00X H 0.335035 0.791170 0.905396 0.113 Uiso 1 1 calc R U . . . C00Y C 0.1163(2) 0.75869(14) 0.8098(4) 0.0850(9) Uani 1 1 d . . . . . H00Y H 0.056445 0.777228 0.801617 0.102 Uiso 1 1 calc R U . . . C00Z C 0.3705(3) 0.39966(18) 0.1345(5) 0.1199(14) Uani 1 1 d . . . . . H00D H 0.303218 0.390706 0.113011 0.144 Uiso 1 1 calc R U . . . H00E H 0.379013 0.429333 0.222944 0.144 Uiso 1 1 calc R U . . . C010 C 0.4043(4) 0.42578(19) -0.0013(5) 0.1318(16) Uani 1 1 d . . . . . H01A H 0.394573 0.396595 -0.089077 0.198 Uiso 1 1 calc R U . . . H01B H 0.470909 0.434543 0.020510 0.198 Uiso 1 1 calc R U . . . H01C H 0.370791 0.464208 -0.029006 0.198 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 Cl01 0.0505(3) 0.0789(5) 0.0747(4) 0.0060(3) 0.0096(3) -0.0158(3) O002 0.0456(8) 0.0633(10) 0.0454(8) -0.0010(7) -0.0035(6) 0.0018(7) O003 0.0480(8) 0.0672(10) 0.0422(8) -0.0065(7) 0.0119(6) 0.0024(7) O004 0.0425(8) 0.0697(11) 0.0635(10) 0.0046(8) -0.0051(7) -0.0115(7) N005 0.0406(8) 0.0422(9) 0.0422(9) -0.0014(7) -0.0005(7) 0.0013(7) N006 0.0440(9) 0.0436(10) 0.0376(8) -0.0029(7) 0.0074(7) -0.0011(7) N007 0.0390(8) 0.0503(10) 0.0461(9) 0.0047(7) 0.0084(7) 0.0081(7) N008 0.0457(9) 0.0623(12) 0.0367(9) -0.0022(8) -0.0062(7) -0.0016(8) O009 0.0793(13) 0.0939(15) 0.1088(16) -0.0371(12) 0.0433(12) -0.0125(11) C00A 0.0396(10) 0.0465(11) 0.0326(9) -0.0041(8) 0.0050(7) 0.0027(8) C00B 0.0412(10) 0.0531(12) 0.0300(9) 0.0011(8) 0.0059(8) -0.0042(9) O00C 0.1302(18) 0.0764(13) 0.0717(12) 0.0052(10) 0.0411(12) 0.0324(12) C00D 0.0327(9) 0.0557(13) 0.0360(10) -0.0009(9) 0.0014(8) -0.0021(8) C00E 0.0350(9) 0.0485(11) 0.0335(9) -0.0023(8) 0.0025(7) 0.0026(8) C00F 0.0442(11) 0.0502(12) 0.0351(10) -0.0048(9) 0.0010(8) 0.0026(9) C00G 0.0422(10) 0.0509(13) 0.0423(10) 0.0023(9) -0.0015(8) 0.0011(9) C00H 0.0406(10) 0.0547(13) 0.0398(10) 0.0027(9) 0.0023(8) -0.0031(9) C00I 0.0383(10) 0.0517(12) 0.0374(10) -0.0012(8) 0.0032(8) 0.0025(9) C00J 0.0395(10) 0.0481(12) 0.0429(11) -0.0064(9) 0.0004(8) 0.0028(9) C00K 0.0437(11) 0.0506(12) 0.0479(11) -0.0016(9) 0.0088(9) -0.0012(9) C00L 0.0546(12) 0.0491(12) 0.0390(10) 0.0016(9) 0.0080(9) -0.0072(10) C00M 0.0625(14) 0.0584(14) 0.0435(11) 0.0055(10) 0.0141(10) -0.0045(11) C00N 0.0640(14) 0.0640(14) 0.0346(10) 0.0041(10) 0.0009(9) -0.0007(11) C00O 0.0611(14) 0.0530(14) 0.0602(14) 0.0070(11) 0.0043(11) 0.0091(11) C00P 0.0623(14) 0.0683(16) 0.0510(12) 0.0086(11) 0.0124(11) -0.0051(12) C00Q 0.0683(15) 0.0686(17) 0.0576(14) -0.0153(12) 0.0157(12) -0.0081(13) C00R 0.0848(18) 0.0520(15) 0.0784(17) 0.0178(13) 0.0016(15) 0.0022(13) C00S 0.0662(16) 0.0572(16) 0.0892(19) 0.0001(13) 0.0020(13) -0.0132(12) C00T 0.0656(15) 0.0548(15) 0.0878(19) -0.0075(13) 0.0098(13) -0.0015(12) C00U 0.0812(18) 0.0701(18) 0.0723(17) 0.0248(14) 0.0183(14) -0.0038(14) C00V 0.108(2) 0.076(2) 0.0795(19) 0.0080(15) 0.0255(17) 0.0085(17) C00W 0.117(3) 0.0470(15) 0.094(2) -0.0069(15) 0.0202(19) -0.0101(17) C00X 0.099(2) 0.0556(18) 0.125(3) -0.0062(17) -0.004(2) -0.0229(17) C00Y 0.088(2) 0.0631(18) 0.106(2) -0.0068(16) 0.0190(17) 0.0147(16) C00Z 0.174(4) 0.087(3) 0.104(3) 0.011(2) 0.039(3) 0.057(3) C010 0.200(5) 0.099(3) 0.101(3) 0.020(2) 0.036(3) 0.048(3) 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' Cl Cl 0.1484 0.1585 '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' 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 C00B N005 N006 117.11(16) . . ? C00B N005 H005 121.4 . . ? N006 N005 H005 121.4 . . ? C00D N006 N005 117.64(15) . . ? C00D N006 C00E 122.63(16) . . ? N005 N006 C00E 118.36(15) . . ? C00G N007 C00E 118.77(15) . . ? C00G N007 H007 120.6 . . ? C00E N007 H007 120.6 . . ? C00J N008 C00F 111.92(16) . . ? C00J N008 H008 124.0 . . ? C00F N008 H008 124.0 . . ? C00I C00A C00F 120.66(18) . . ? C00I C00A C00E 130.50(17) . . ? C00F C00A C00E 108.83(16) . . ? O002 C00B N005 121.74(19) . . ? O002 C00B C00L 122.05(18) . . ? N005 C00B C00L 116.19(17) . . ? C00Q O00C C00Z 116.3(2) . . ? O003 C00D N006 120.62(19) . . ? O003 C00D C00H 124.07(18) . . ? N006 C00D C00H 115.20(17) . . ? N007 C00E N006 107.83(15) . . ? N007 C00E C00A 113.54(15) . . ? N006 C00E C00A 112.62(16) . . ? N007 C00E C00J 111.48(16) . . ? N006 C00E C00J 109.52(14) . . ? C00A C00E C00J 101.77(15) . . ? C00N C00F C00A 121.60(19) . . ? C00N C00F N008 128.43(18) . . ? C00A C00F N008 109.97(17) . . ? N007 C00G C00O 121.71(19) . . ? N007 C00G C00H 119.23(19) . . ? C00O C00G C00H 119.0(2) . . ? C00P C00H C00G 119.9(2) . . ? C00P C00H C00D 120.04(19) . . ? C00G C00H C00D 119.90(18) . . ? C00A C00I C00K 117.31(18) . . ? C00A C00I H00I 121.3 . . ? C00K C00I H00I 121.3 . . ? O004 C00J N008 127.81(19) . . ? O004 C00J C00E 124.72(18) . . ? N008 C00J C00E 107.47(16) . . ? C00M C00K C00I 121.89(19) . . ? C00M C00K Cl01 119.42(16) . . ? C00I C00K Cl01 118.68(16) . . ? C00T C00L C00S 119.0(2) . . ? C00T C00L C00B 124.0(2) . . ? C00S C00L C00B 117.0(2) . . ? C00N C00M C00K 120.7(2) . . ? C00N C00M H00M 119.6 . . ? C00K C00M H00M 119.6 . . ? C00M C00N C00F 117.81(19) . . ? C00M C00N H00N 121.1 . . ? C00F C00N H00N 121.1 . . ? C00R C00O C00G 119.4(2) . . ? C00R C00O H00O 120.3 . . ? C00G C00O H00O 120.3 . . ? C00U C00P C00H 120.6(2) . . ? C00U C00P H00P 119.7 . . ? C00H C00P H00P 119.7 . . ? O009 C00Q O00C 123.0(3) . . ? O009 C00Q C00V 125.1(3) . . ? O00C C00Q C00V 111.9(2) . . ? C00U C00R C00O 121.7(2) . . ? C00U C00R H00R 119.1 . . ? C00O C00R H00R 119.1 . . ? C00X C00S C00L 120.3(3) . . ? C00X C00S H00S 119.8 . . ? C00L C00S H00S 119.8 . . ? C00L C00T C00Y 119.8(3) . . ? C00L C00T H00T 120.1 . . ? C00Y C00T H00T 120.1 . . ? C00P C00U C00R 119.3(2) . . ? C00P C00U H00U 120.4 . . ? C00R C00U H00U 120.4 . . ? C00Q C00V H00A 109.5 . . ? C00Q C00V H00B 109.5 . . ? H00A C00V H00B 109.5 . . ? C00Q C00V H00C 109.5 . . ? H00A C00V H00C 109.5 . . ? H00B C00V H00C 109.5 . . ? C00X C00W C00Y 120.1(3) . . ? C00X C00W H00W 120.0 . . ? C00Y C00W H00W 120.0 . . ? C00W C00X C00S 120.5(3) . . ? C00W C00X H00X 119.8 . . ? C00S C00X H00X 119.8 . . ? C00W C00Y C00T 120.3(3) . . ? C00W C00Y H00Y 119.8 . . ? C00T C00Y H00Y 119.8 . . ? C010 C00Z O00C 109.5(3) . . ? C010 C00Z H00D 109.8 . . ? O00C C00Z H00D 109.8 . . ? C010 C00Z H00E 109.8 . . ? O00C C00Z H00E 109.8 . . ? H00D C00Z H00E 108.2 . . ? C00Z C010 H01A 109.5 . . ? C00Z C010 H01B 109.5 . . ? H01A C010 H01B 109.5 . . ? C00Z C010 H01C 109.5 . . ? H01A C010 H01C 109.5 . . ? H01B C010 H01C 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 Cl01 C00K 1.736(2) . ? O002 C00B 1.211(2) . ? O003 C00D 1.228(2) . ? O004 C00J 1.213(2) . ? N005 C00B 1.368(2) . ? N005 N006 1.384(2) . ? N005 H005 0.8600 . ? N006 C00D 1.374(2) . ? N006 C00E 1.469(2) . ? N007 C00G 1.381(3) . ? N007 C00E 1.440(3) . ? N007 H007 0.8600 . ? N008 C00J 1.343(3) . ? N008 C00F 1.405(3) . ? N008 H008 0.8600 . ? O009 C00Q 1.196(3) . ? C00A C00I 1.379(3) . ? C00A C00F 1.390(3) . ? C00A C00E 1.497(3) . ? C00B C00L 1.491(3) . ? O00C C00Q 1.310(3) . ? O00C C00Z 1.462(4) . ? C00D C00H 1.461(3) . ? C00E C00J 1.573(3) . ? C00F C00N 1.377(3) . ? C00G C00O 1.394(3) . ? C00G C00H 1.402(3) . ? C00H C00P 1.392(3) . ? C00I C00K 1.385(3) . ? C00I H00I 0.9300 . ? C00K C00M 1.380(3) . ? C00L C00T 1.379(3) . ? C00L C00S 1.381(3) . ? C00M C00N 1.376(3) . ? C00M H00M 0.9300 . ? C00N H00N 0.9300 . ? C00O C00R 1.380(3) . ? C00O H00O 0.9300 . ? C00P C00U 1.368(4) . ? C00P H00P 0.9300 . ? C00Q C00V 1.472(4) . ? C00R C00U 1.377(4) . ? C00R H00R 0.9300 . ? C00S C00X 1.377(4) . ? C00S H00S 0.9300 . ? C00T C00Y 1.387(4) . ? C00T H00T 0.9300 . ? C00U H00U 0.9300 . ? C00V H00A 0.9600 . ? C00V H00B 0.9600 . ? C00V H00C 0.9600 . ? C00W C00X 1.355(4) . ? C00W C00Y 1.364(4) . ? C00W H00W 0.9300 . ? C00X H00X 0.9300 . ? C00Y H00Y 0.9300 . ? C00Z C010 1.391(5) . ? C00Z H00D 0.9700 . ? C00Z H00E 0.9700 . ? C010 H01A 0.9600 . ? C010 H01B 0.9600 . ? C010 H01C 0.9600 . ? 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 C00B N005 N006 C00D 85.1(2) . . . . ? C00B N005 N006 C00E -107.85(18) . . . . ? N006 N005 C00B O002 16.9(3) . . . . ? N006 N005 C00B C00L -164.74(15) . . . . ? N005 N006 C00D O003 -0.4(3) . . . . ? C00E N006 C00D O003 -166.79(17) . . . . ? N005 N006 C00D C00H -176.74(16) . . . . ? C00E N006 C00D C00H 16.8(2) . . . . ? C00G N007 C00E N006 45.3(2) . . . . ? C00G N007 C00E C00A 170.79(16) . . . . ? C00G N007 C00E C00J -75.0(2) . . . . ? C00D N006 C00E N007 -41.7(2) . . . . ? N005 N006 C00E N007 151.98(16) . . . . ? C00D N006 C00E C00A -167.73(16) . . . . ? N005 N006 C00E C00A 25.9(2) . . . . ? C00D N006 C00E C00J 79.8(2) . . . . ? N005 N006 C00E C00J -86.54(19) . . . . ? C00I C00A C00E N007 -58.9(3) . . . . ? C00F C00A C00E N007 121.88(18) . . . . ? C00I C00A C00E N006 64.0(3) . . . . ? C00F C00A C00E N006 -115.21(18) . . . . ? C00I C00A C00E C00J -178.9(2) . . . . ? C00F C00A C00E C00J 2.0(2) . . . . ? C00I C00A C00F C00N -0.2(3) . . . . ? C00E C00A C00F C00N 179.05(19) . . . . ? C00I C00A C00F N008 179.38(18) . . . . ? C00E C00A C00F N008 -1.3(2) . . . . ? C00J N008 C00F C00N 179.5(2) . . . . ? C00J N008 C00F C00A 0.0(2) . . . . ? C00E N007 C00G C00O 157.18(19) . . . . ? C00E N007 C00G C00H -26.0(3) . . . . ? N007 C00G C00H C00P -179.12(19) . . . . ? C00O C00G C00H C00P -2.2(3) . . . . ? N007 C00G C00H C00D -2.9(3) . . . . ? C00O C00G C00H C00D 174.07(19) . . . . ? O003 C00D C00H C00P 7.3(3) . . . . ? N006 C00D C00H C00P -176.41(18) . . . . ? O003 C00D C00H C00G -168.89(18) . . . . ? N006 C00D C00H C00G 7.4(3) . . . . ? C00F C00A C00I C00K 0.5(3) . . . . ? C00E C00A C00I C00K -178.65(19) . . . . ? C00F N008 C00J O004 -177.9(2) . . . . ? C00F N008 C00J C00E 1.3(2) . . . . ? N007 C00E C00J O004 55.9(3) . . . . ? N006 C00E C00J O004 -63.3(3) . . . . ? C00A C00E C00J O004 177.3(2) . . . . ? N007 C00E C00J N008 -123.32(17) . . . . ? N006 C00E C00J N008 117.42(17) . . . . ? C00A C00E C00J N008 -2.0(2) . . . . ? C00A C00I C00K C00M -1.0(3) . . . . ? C00A C00I C00K Cl01 178.84(15) . . . . ? O002 C00B C00L C00T -159.6(2) . . . . ? N005 C00B C00L C00T 22.0(3) . . . . ? O002 C00B C00L C00S 16.9(3) . . . . ? N005 C00B C00L C00S -161.5(2) . . . . ? C00I C00K C00M C00N 1.2(3) . . . . ? Cl01 C00K C00M C00N -178.56(18) . . . . ? C00K C00M C00N C00F -0.9(3) . . . . ? C00A C00F C00N C00M 0.4(3) . . . . ? N008 C00F C00N C00M -179.1(2) . . . . ? N007 C00G C00O C00R 178.3(2) . . . . ? C00H C00G C00O C00R 1.5(3) . . . . ? C00G C00H C00P C00U 1.2(3) . . . . ? C00D C00H C00P C00U -175.0(2) . . . . ? C00Z O00C C00Q O009 -0.6(4) . . . . ? C00Z O00C C00Q C00V 179.0(3) . . . . ? C00G C00O C00R C00U 0.2(4) . . . . ? C00T C00L C00S C00X -0.8(4) . . . . ? C00B C00L C00S C00X -177.4(3) . . . . ? C00S C00L C00T C00Y 0.3(4) . . . . ? C00B C00L C00T C00Y 176.7(2) . . . . ? C00H C00P C00U C00R 0.5(4) . . . . ? C00O C00R C00U C00P -1.2(4) . . . . ? C00Y C00W C00X C00S 1.6(5) . . . . ? C00L C00S C00X C00W -0.1(5) . . . . ? C00X C00W C00Y C00T -2.0(5) . . . . ? C00L C00T C00Y C00W 1.1(5) . . . . ? C00Q O00C C00Z C010 -179.6(4) . . . . ?