#------------------------------------------------------------------------------ #$Date: 2016-03-08 09:14:09 +0200 (Tue, 08 Mar 2016) $ #$Revision: 178016 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/45/7224543.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_7224543 loop_ _publ_author_name 'PASHA, MOHAMED AFZAL' 'tabassum, sumaiya' 'govindaraju, santhosh' 'rahaman khan, riyaz ur' _publ_section_title ; Ultrasound mediated, green innovation for the synthesis of polysubstituted 1,4-dihydropyridines ; _journal_name_full 'RSC Adv.' _journal_paper_doi 10.1039/C6RA05441B _journal_year 2016 _chemical_formula_sum 'C26 H23 N3 O5' _chemical_formula_weight 456.46 _chemical_melting_point 455.6(5) _chemical_name_systematic 'Diethyl 6-amino-4-(benzofuran-2-yl)-5-cyano-1-phenyl-1,4-dihydropyridine-2,3-dicarboxylate ' _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2015-09-08 deposited with the CCDC. 2016-03-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 109.875(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.4240(6) _cell_length_b 21.2481(11) _cell_length_c 11.2337(6) _cell_measurement_temperature 296(2) _cell_volume 2340.0(2) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_unetI/netI 0.0079 _diffrn_reflns_laue_measured_fraction_full 1.000 _diffrn_reflns_laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 17287 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 14.997 _diffrn_reflns_theta_max 14.997 _diffrn_reflns_theta_min 1.917 _exptl_absorpt_coefficient_mu 0.091 _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.296 _exptl_crystal_F_000 956 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ethanol' _refine_diff_density_max 0.215 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.019 _refine_ls_extinction_coef 0.0042(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 334 _refine_ls_number_reflns 945 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.899 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0276 _refine_ls_shift/su_max 0.067 _refine_ls_shift/su_mean 0.015 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+3.1962P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.0654 _reflns_Friedel_coverage 0.000 _reflns_number_gt 908 _reflns_number_total 945 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ra05441b2.cif _cod_data_source_block NITK366_a_a _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '182-183C' was changed to '455.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K), the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas ; _cod_database_code 7224543 _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_res_file ; NITK366_a_a.res created by SHELXL-2014/7 TITL NITK366_a_a.res in P2(1)/c CELL 0.71073 10.4240 21.2481 11.2337 90.000 109.875 90.000 ZERR 4.000 0.0006 0.0011 0.0006 0.000 0.002 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 104 88 12 20 OMIT -3 30 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 FREE C00V H27 TEMP 23.000 WGHT 0.033900 3.196200 EXTI 0.004163 FVAR 0.60106 O001 4 0.317663 0.516777 0.332103 11.00000 0.06334 0.04909 = 0.07277 -0.01036 0.03853 0.00053 O002 4 0.113394 0.468344 0.269640 11.00000 0.07556 0.05640 = 0.06508 -0.01948 0.02746 -0.01654 O003 4 0.344360 0.647418 0.679720 11.00000 0.06218 0.05452 = 0.08227 -0.00649 0.02800 -0.01348 N1 3 0.101981 0.608072 0.368208 11.00000 0.06437 0.02299 = 0.03858 0.00477 0.02132 0.01379 O1 4 0.291626 0.441792 0.538446 11.00000 0.10692 0.03547 = 0.07608 0.00878 0.04113 0.03039 O006 4 0.222529 0.457984 0.702511 11.00000 0.11464 0.06000 = 0.05902 0.02123 0.03441 0.01457 N007 3 -0.024884 0.697678 0.369428 11.00000 0.08847 0.04955 = 0.04716 0.00969 0.03342 0.03239 AFIX 93 H21 2 -0.065797 0.722996 0.404405 11.00000 -1.20000 H22 2 -0.027074 0.704459 0.293288 11.00000 -1.20000 AFIX 0 C1 1 0.158082 0.551103 0.422824 11.00000 0.04472 0.02751 = 0.04155 -0.00767 0.01828 0.00049 C009 1 0.049581 0.634228 0.555487 11.00000 0.05197 0.03449 = 0.02588 0.00745 0.00483 0.01115 C00A 1 0.042781 0.647287 0.434048 11.00000 0.04459 0.01748 = 0.05046 -0.00374 0.00789 0.01335 C00B 1 0.140299 0.582757 0.629517 11.00000 0.03648 0.03496 = 0.04256 -0.00149 0.01845 -0.00428 AFIX 13 H00B 2 0.089739 0.560150 0.675497 11.00000 -1.20000 AFIX 0 C00C 1 0.174227 0.535999 0.543683 11.00000 0.04283 0.02137 = 0.04260 -0.00042 0.01502 0.01056 C00D 1 0.192348 0.506176 0.332585 11.00000 0.05015 0.03851 = 0.05011 0.01125 0.02073 0.00745 C00E 1 0.101925 0.625289 0.243920 11.00000 0.06380 0.04305 = 0.02432 0.00710 0.01737 0.00884 C00F 1 0.267852 0.607631 0.725467 11.00000 0.03668 0.03922 = 0.04977 -0.00281 0.01698 -0.00496 C00G 1 0.228719 0.475614 0.601869 11.00000 0.05292 0.02482 = 0.05577 -0.00627 0.00574 0.00999 C00H 1 -0.016211 0.675386 0.615643 11.00000 0.06297 0.03842 = 0.03600 -0.00327 0.01193 0.00919 N00I 3 -0.067252 0.708798 0.663729 11.00000 0.09568 0.06802 = 0.05712 -0.01496 0.02665 0.02354 C00J 1 0.326168 0.599242 0.849024 11.00000 0.06434 0.07885 = 0.03327 -0.00205 0.00751 -0.00485 AFIX 43 H24 2 0.292140 0.574170 0.899305 11.00000 -1.20000 AFIX 0 C00K 1 0.004982 0.602180 0.139888 11.00000 0.08422 0.07562 = 0.03173 -0.00139 0.01540 0.01176 AFIX 43 H17 2 -0.062578 0.575650 0.147894 11.00000 -1.20000 AFIX 0 C00L 1 0.456062 0.662542 0.786698 11.00000 0.05038 0.04239 = 0.13312 -0.02995 0.03906 -0.01593 C00M 1 0.200483 0.665795 0.232328 11.00000 0.07272 0.06293 = 0.06005 0.01177 0.03316 0.00137 C00N 1 0.447951 0.634348 0.892145 11.00000 0.06725 0.07027 = 0.07746 -0.02513 0.01390 0.00353 C00O 1 0.364528 0.476988 0.249709 11.00000 0.09241 0.06288 = 0.10086 -0.01297 0.06338 0.01525 AFIX 23 H12 2 0.321682 0.435966 0.242297 11.00000 -1.20000 H29 2 0.462421 0.471197 0.286775 11.00000 -1.20000 AFIX 0 C00P 1 0.007212 0.618396 0.021163 11.00000 0.11071 0.09576 = 0.03838 -0.01484 -0.00393 0.03442 C00Q 1 0.104868 0.658243 0.009231 11.00000 0.16117 0.09550 = 0.06688 0.02961 0.06306 0.06450 C00R 1 0.200001 0.681791 0.113427 11.00000 0.11458 0.09199 = 0.09906 0.03952 0.07992 0.02482 C00S 1 0.353485 0.382743 0.590988 11.00000 0.17123 0.02064 = 0.10163 0.01487 0.06687 0.04982 AFIX 23 H10 2 0.412386 0.388670 0.678040 11.00000 -1.20000 H11 2 0.283406 0.352488 0.589887 11.00000 -1.20000 AFIX 0 C00T 1 0.666120 0.709873 0.902212 11.00000 0.15204 0.08883 = 0.21315 -0.00739 0.11120 0.00287 C00U 1 0.331595 0.505065 0.123236 11.00000 0.18865 0.09217 = 0.08084 0.01074 0.08095 0.03244 AFIX 137 H14 2 0.234364 0.507896 0.083910 11.00000 -1.50000 H13 2 0.368227 0.479222 0.072408 11.00000 -1.50000 H15 2 0.370687 0.546412 0.130791 11.00000 -1.50000 AFIX 0 C00V 1 0.559846 0.702225 0.780712 11.00000 0.12451 0.09271 = 0.13695 -0.03062 0.02679 0.00465 C00W 1 0.431420 0.359871 0.516673 11.00000 0.12601 0.07109 = 0.21104 0.01293 0.06386 0.03370 AFIX 137 H8 2 0.371099 0.349629 0.433171 11.00000 -1.50000 H7 2 0.480890 0.322914 0.555793 11.00000 -1.50000 H9 2 0.494474 0.391750 0.511278 11.00000 -1.50000 AFIX 0 C00X 1 0.557254 0.645029 1.008089 11.00000 0.10449 0.12282 = 0.07835 -0.04392 -0.02817 0.01530 AFIX 43 H25 2 0.558591 0.626720 1.083698 11.00000 -1.20000 AFIX 0 C00Y 1 0.659717 0.683531 1.002145 11.00000 0.04890 0.09717 = 0.25860 -0.09750 -0.00339 -0.02114 AFIX 43 H26 2 0.730940 0.691228 1.077327 11.00000 -1.20000 AFIX 0 H28 2 0.540681 0.713473 0.679873 11.00000 0.06353 H18 2 0.099699 0.668955 -0.076114 11.00000 0.12275 H20 2 0.267707 0.680768 0.314031 11.00000 0.07213 H16 2 -0.061439 0.601203 -0.046146 11.00000 0.05098 H27 2 0.699788 0.729697 0.828052 11.00000 0.09571 H19 2 0.269324 0.707182 0.104469 11.00000 0.11236 HKLF 4 REM NITK366_a_a.res in P2(1)/c REM R1 = 0.0276 for 908 Fo > 4sig(Fo) and 0.0286 for all 945 data REM 334 parameters refined using 0 restraints END WGHT 0.0307 2.3245 REM Highest difference peak 0.215, deepest hole -0.120, 1-sigma level 0.019 Q1 1 0.5000 0.3771 0.6623 11.00000 0.05 0.22 Q2 1 -0.0010 0.7530 0.4442 11.00000 0.05 0.10 Q3 1 0.2790 0.3672 0.6637 11.00000 0.05 0.09 Q4 1 0.7936 0.7535 0.9458 11.00000 0.05 0.08 Q5 1 0.4603 0.3168 0.5089 11.00000 0.05 0.07 Q6 1 0.0568 0.7277 0.3114 11.00000 0.05 0.06 Q7 1 0.4908 0.6602 0.6658 11.00000 0.05 0.06 Q8 1 0.5363 0.6665 0.6848 11.00000 0.05 0.05 Q9 1 0.1790 0.4335 0.4981 11.00000 0.05 0.05 Q10 1 0.4809 0.5175 0.2092 11.00000 0.05 0.05 Q11 1 0.7527 0.6738 1.1913 11.00000 0.05 0.05 Q12 1 0.0057 0.6391 -0.1255 11.00000 0.05 0.05 Q13 1 0.3081 0.3550 0.4947 11.00000 0.05 0.05 Q14 1 0.4764 0.3862 0.4792 11.00000 0.05 0.05 Q15 1 0.5198 0.7537 0.7241 11.00000 0.05 0.05 Q16 1 0.2679 0.3467 0.4657 11.00000 0.05 0.05 Q17 1 0.0359 0.6859 0.7302 11.00000 0.05 0.05 Q18 1 -0.1051 0.6584 0.6840 11.00000 0.05 0.05 Q19 1 -0.1119 0.5774 0.1754 11.00000 0.05 0.05 Q20 1 0.2364 0.4170 0.7896 11.00000 0.05 0.04 ; _shelx_res_checksum 44885 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 O001 O 0.3177(5) 0.51678(14) 0.3321(3) 0.0578(12) Uani 1 1 d . . O002 O 0.1134(4) 0.46834(18) 0.2696(3) 0.0648(14) Uani 1 1 d . . O003 O 0.3444(10) 0.6474(3) 0.6797(5) 0.0654(13) Uani 1 1 d . . N1 N 0.1020(7) 0.6081(5) 0.3682(9) 0.0410(15) Uani 1 1 d . . O1 O 0.2916(5) 0.4418(3) 0.5384(4) 0.0703(15) Uani 1 1 d . . O006 O 0.2225(4) 0.4580(2) 0.7025(4) 0.0766(17) Uani 1 1 d . . N007 N -0.0249(4) 0.6977(2) 0.3694(4) 0.0591(15) Uani 1 1 d . . H21 H -0.0658 0.7230 0.4044 0.071 Uiso 1 1 calc R U H22 H -0.0271 0.7045 0.2933 0.071 Uiso 1 1 calc R U C1 C 0.1581(7) 0.5511(6) 0.4228(14) 0.0370(18) Uani 1 1 d . . C009 C 0.0496(6) 0.6342(4) 0.5555(12) 0.040(2) Uani 1 1 d . . C00A C 0.0428(6) 0.6473(4) 0.4340(13) 0.0396(17) Uani 1 1 d . . C00B C 0.1403(9) 0.5828(5) 0.6295(8) 0.0367(15) Uani 1 1 d . . H00B H 0.0897 0.5601 0.6755 0.044 Uiso 1 1 calc R U C00C C 0.1742(6) 0.5360(5) 0.5437(14) 0.0355(18) Uani 1 1 d . . C00D C 0.1923(8) 0.5062(4) 0.3326(7) 0.0453(17) Uani 1 1 d . . C00E C 0.1019(15) 0.6253(5) 0.2439(14) 0.0431(18) Uani 1 1 d . . C00F C 0.2679(9) 0.6076(4) 0.7255(14) 0.0413(16) Uani 1 1 d . . C00G C 0.2287(7) 0.4756(5) 0.6019(8) 0.0478(18) Uani 1 1 d . . C00H C -0.0162(6) 0.6754(3) 0.6156(6) 0.0471(19) Uani 1 1 d . . N00I N -0.0673(5) 0.7088(3) 0.6637(5) 0.0734(17) Uani 1 1 d . . C00J C 0.3262(14) 0.5992(3) 0.8490(14) 0.061(2) Uani 1 1 d . . H24 H 0.2921 0.5742 0.8993 0.073 Uiso 1 1 calc R U C00K C 0.0050(12) 0.6022(3) 0.1399(19) 0.065(2) Uani 1 1 d . . H17 H -0.0626 0.5757 0.1479 0.078 Uiso 1 1 calc R U C00L C 0.4561(12) 0.6625(5) 0.787(2) 0.073(3) Uani 1 1 d . . C00M C 0.2005(12) 0.6658(6) 0.2323(12) 0.063(2) Uani 1 1 d . . C00N C 0.4480(15) 0.6343(6) 0.8921(14) 0.074(3) Uani 1 1 d . . C00O C 0.3645(5) 0.4770(2) 0.2497(6) 0.0776(18) Uani 1 1 d . . H12 H 0.3217 0.4360 0.2423 0.093 Uiso 1 1 calc R U H29 H 0.4624 0.4712 0.2868 0.093 Uiso 1 1 calc R U C00P C 0.0072(13) 0.6184(6) 0.0212(17) 0.089(3) Uani 1 1 d . . C00Q C 0.105(2) 0.6582(7) 0.0092(14) 0.102(4) Uani 1 1 d . . C00R C 0.2000(13) 0.6818(4) 0.113(2) 0.091(3) Uani 1 1 d . . C00S C 0.3535(8) 0.3827(3) 0.5910(5) 0.093(2) Uani 1 1 d . . H10 H 0.4124 0.3887 0.6780 0.111 Uiso 1 1 calc R U H11 H 0.2834 0.3525 0.5899 0.111 Uiso 1 1 calc R U C00T C 0.6661(17) 0.7099(5) 0.9022(18) 0.139(5) Uani 1 1 d . . C00U C 0.3316(6) 0.5051(3) 0.1232(6) 0.112(2) Uani 1 1 d . . H14 H 0.2344 0.5079 0.0839 0.167 Uiso 1 1 calc R U H13 H 0.3682 0.4792 0.0724 0.167 Uiso 1 1 calc R U H15 H 0.3707 0.5464 0.1308 0.167 Uiso 1 1 calc R U C00V C 0.5598(18) 0.7022(5) 0.7807(13) 0.123(3) Uani 1 1 d . . C00W C 0.4314(6) 0.3599(3) 0.5167(7) 0.134(2) Uani 1 1 d . . H8 H 0.3711 0.3496 0.4332 0.202 Uiso 1 1 calc R U H7 H 0.4809 0.3229 0.5558 0.202 Uiso 1 1 calc R U H9 H 0.4945 0.3918 0.5113 0.202 Uiso 1 1 calc R U C00X C 0.5573(17) 0.6450(5) 1.0081(9) 0.117(3) Uani 1 1 d . . H25 H 0.5586 0.6267 1.0837 0.140 Uiso 1 1 calc R U C00Y C 0.6597(13) 0.6835(6) 1.0021(14) 0.149(6) Uani 1 1 d . . H26 H 0.7309 0.6912 1.0773 0.179 Uiso 1 1 calc R U H28 H 0.541(4) 0.7135(18) 0.680(4) 0.06(2) Uiso 1 1 d . . H18 H 0.100(5) 0.669(2) -0.076(6) 0.12(3) Uiso 1 1 d . . H20 H 0.268(5) 0.681(2) 0.314(5) 0.07(3) Uiso 1 1 d . . H16 H -0.061(4) 0.6012(18) -0.046(5) 0.05(2) Uiso 1 1 d . . H27 H 0.700(5) 0.730(2) 0.828(5) 0.10(2) Uiso 1 1 d . . H19 H 0.269(5) 0.707(2) 0.104(6) 0.11(3) 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 O001 0.063(3) 0.049(3) 0.073(3) -0.010(2) 0.039(2) 0.001(2) O002 0.076(3) 0.056(3) 0.065(3) -0.019(2) 0.027(2) -0.017(2) O003 0.062(4) 0.055(3) 0.082(4) -0.006(3) 0.028(5) -0.013(3) N1 0.064(3) 0.023(6) 0.039(8) 0.005(6) 0.021(4) 0.014(4) O1 0.107(3) 0.035(4) 0.076(3) 0.009(3) 0.041(3) 0.030(3) O006 0.115(3) 0.060(3) 0.059(3) 0.021(3) 0.034(3) 0.015(2) N007 0.088(3) 0.050(3) 0.047(3) 0.010(3) 0.033(2) 0.032(3) C1 0.045(4) 0.028(9) 0.042(9) -0.008(9) 0.018(5) 0.000(5) C009 0.052(5) 0.034(8) 0.026(8) 0.007(6) 0.005(5) 0.011(6) C00A 0.045(5) 0.017(7) 0.050(9) -0.004(8) 0.008(6) 0.013(5) C00B 0.036(5) 0.035(5) 0.043(7) -0.001(7) 0.018(6) -0.004(5) C00C 0.043(4) 0.021(9) 0.043(8) 0.000(9) 0.015(5) 0.011(4) C00D 0.050(7) 0.039(6) 0.050(6) 0.011(5) 0.021(5) 0.007(5) C00E 0.064(6) 0.043(6) 0.024(12) 0.007(7) 0.017(9) 0.009(5) C00F 0.037(7) 0.039(5) 0.050(10) -0.003(5) 0.017(9) -0.005(5) C00G 0.053(4) 0.025(8) 0.056(8) -0.006(9) 0.006(5) 0.010(4) C00H 0.063(5) 0.038(7) 0.036(6) -0.003(4) 0.012(4) 0.009(5) N00I 0.096(4) 0.068(4) 0.057(4) -0.015(3) 0.027(3) 0.024(3) C00J 0.064(8) 0.079(5) 0.033(8) -0.002(6) 0.008(6) -0.005(6) C00K 0.084(8) 0.076(5) 0.032(8) -0.001(8) 0.015(8) 0.012(5) C00L 0.050(10) 0.042(6) 0.133(16) -0.030(8) 0.039(12) -0.016(7) C00M 0.073(8) 0.063(6) 0.060(14) 0.012(7) 0.033(9) 0.001(6) C00N 0.067(11) 0.070(7) 0.077(13) -0.025(8) 0.014(12) 0.004(7) C00O 0.092(5) 0.063(4) 0.101(5) -0.013(5) 0.063(4) 0.015(3) C00P 0.111(10) 0.096(7) 0.038(12) -0.015(8) -0.004(9) 0.034(8) C00Q 0.161(14) 0.095(9) 0.067(13) 0.030(10) 0.063(12) 0.065(9) C00R 0.115(10) 0.092(7) 0.099(12) 0.040(9) 0.080(10) 0.025(8) C00S 0.171(6) 0.021(5) 0.102(5) 0.015(4) 0.067(5) 0.050(4) C00T 0.152(13) 0.089(8) 0.213(16) -0.007(9) 0.111(13) 0.003(8) C00U 0.189(6) 0.092(5) 0.081(5) 0.011(4) 0.081(4) 0.032(4) C00V 0.125(11) 0.093(7) 0.137(14) -0.031(9) 0.027(10) 0.005(8) C00W 0.126(6) 0.071(5) 0.211(8) 0.013(5) 0.064(6) 0.034(4) C00X 0.104(8) 0.123(8) 0.078(7) -0.044(6) -0.028(9) 0.015(7) C00Y 0.049(7) 0.097(8) 0.259(19) -0.097(10) -0.003(9) -0.021(6) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C00D O001 C00O 116.6(5) C00F O003 C00L 103.9(8) C00A N1 C1 118.8(8) C00A N1 C00E 120.6(10) C1 N1 C00E 120.6(10) C00G O1 C00S 118.9(7) C00A N007 H21 120.0 C00A N007 H22 120.0 H21 N007 H22 120.0 C00C C1 N1 122.7(9) C00C C1 C00D 123.0(11) N1 C1 C00D 114.2(11) C00A C009 C00H 118.7(9) C00A C009 C00B 120.6(8) C00H C009 C00B 120.1(9) N007 C00A C009 122.5(10) N007 C00A N1 115.8(11) C009 C00A N1 121.8(8) C00F C00B C009 112.4(7) C00F C00B C00C 110.5(7) C009 C00B C00C 111.5(8) C00F C00B H00B 107.4 C009 C00B H00B 107.4 C00C C00B H00B 107.4 C1 C00C C00G 123.7(10) C1 C00C C00B 120.7(9) C00G C00C C00B 115.6(12) O002 C00D O001 126.3(8) O002 C00D C1 123.1(7) O001 C00D C1 110.5(7) C00K C00E C00M 120.5(10) C00K C00E N1 119.9(13) C00M C00E N1 119.6(14) C00J C00F O003 110.9(7) C00J C00F C00B 133.4(12) O003 C00F C00B 115.7(12) O006 C00G O1 121.6(9) O006 C00G C00C 123.4(10) O1 C00G C00C 114.9(8) N00I C00H C009 179.0(6) C00F C00J C00N 109.1(8) C00F C00J H24 125.4 C00N C00J H24 125.4 C00E C00K C00P 119.3(10) C00E C00K H17 120.3 C00P C00K H17 120.3 C00N C00L C00V 126.2(18) C00N C00L O003 111.6(10) C00V C00L O003 122.2(18) C00R C00M C00E 119.2(10) C00R C00M H20 126(3) C00E C00M H20 115(3) C00L C00N C00J 104.5(11) C00L C00N C00X 117.4(17) C00J C00N C00X 138.1(19) O001 C00O C00U 111.1(4) O001 C00O H12 109.4 C00U C00O H12 109.4 O001 C00O H29 109.4 C00U C00O H29 109.4 H12 C00O H29 108.0 C00Q C00P C00K 120.4(12) C00Q C00P H16 124(4) C00K C00P H16 115(4) C00R C00Q C00P 119.9(14) C00R C00Q H18 123(4) C00P C00Q H18 117(4) C00Q C00R C00M 120.7(12) C00Q C00R H19 119(4) C00M C00R H19 120(4) C00W C00S O1 108.6(6) C00W C00S H10 110.0 O1 C00S H10 110.0 C00W C00S H11 110.0 O1 C00S H11 110.0 H10 C00S H11 108.3 C00Y C00T C00V 121.9(17) C00Y C00T H27 165(3) C00V C00T H27 70(3) C00O C00U H14 109.5 C00O C00U H13 109.5 H14 C00U H13 109.5 C00O C00U H15 109.5 H14 C00U H15 109.5 H13 C00U H15 109.5 C00L C00V C00T 112.4(15) C00L C00V H28 108(3) C00T C00V H28 139(3) C00L C00V H27 154(3) C00T C00V H27 44(2) H28 C00V H27 95(3) C00S C00W H8 109.5 C00S C00W H7 109.5 H8 C00W H7 109.5 C00S C00W H9 109.5 H8 C00W H9 109.5 H7 C00W H9 109.5 C00Y C00X C00N 116.5(11) C00Y C00X H25 121.7 C00N C00X H25 121.8 C00T C00Y C00X 125.6(16) C00T C00Y H26 117.2 C00X C00Y H26 117.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O001 C00D 1.327(6) O001 C00O 1.455(5) O002 C00D 1.195(7) O003 C00F 1.376(6) O003 C00L 1.397(11) N1 C00A 1.390(7) N1 C1 1.393(8) N1 C00E 1.443(9) O1 C00G 1.331(7) O1 C00S 1.442(6) O006 C00G 1.213(7) N007 C00A 1.350(7) N007 H21 0.8600 N007 H22 0.8600 C1 C00C 1.349(7) C1 C00D 1.521(10) C009 C00A 1.370(8) C009 C00H 1.417(8) C009 C00B 1.499(8) C00B C00F 1.495(8) C00B C00C 1.508(8) C00B H00B 0.9800 C00C C00G 1.464(9) C00E C00K 1.351(8) C00E C00M 1.380(8) C00F C00J 1.324(8) C00H N00I 1.129(7) C00J C00N 1.409(9) C00J H24 0.9300 C00K C00P 1.385(11) C00K H17 0.9300 C00L C00N 1.355(9) C00L C00V 1.391(13) C00M C00R 1.377(11) C00M H20 1.00(4) C00N C00X 1.427(12) C00O C00U 1.470(6) C00O H12 0.9700 C00O H29 0.9700 C00P C00Q 1.365(11) C00P H16 0.92(4) C00Q C00R 1.347(11) C00Q H18 0.97(6) C00R H19 0.93(5) C00S C00W 1.433(6) C00S H10 0.9700 C00S H11 0.9700 C00T C00Y 1.276(12) C00T C00V 1.445(13) C00T H27 1.09(5) C00U H14 0.9600 C00U H13 0.9600 C00U H15 0.9600 C00V H28 1.11(4) C00V H27 1.49(5) C00W H8 0.9600 C00W H7 0.9600 C00W H9 0.9600 C00X C00Y 1.365(10) C00X H25 0.9300 C00Y H26 0.9300