#------------------------------------------------------------------------------ #$Date: 2018-01-26 11:30:02 +0200 (Fri, 26 Jan 2018) $ #$Revision: 205752 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119079.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_7119079 loop_ _publ_author_name 'Rong-Guo Shi' 'Xiao-Hua Wang' 'Ruzhang Liu' 'Chao-Guo Yan' _publ_section_title ; Two-carbon ring expansion of isatin: a convenient construction of a dibenzo[b,d]azepinone scaffold ; _journal_name_full Chem.Commun. _journal_page_first 6280 _journal_volume 52 _journal_year 2016 _chemical_formula_sum 'C25 H17 Cl N2 O5' _chemical_formula_weight 460.88 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_block_doi 10.5517/cc1kkq2x _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2016-01-13 deposited with the CCDC. 2016-04-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.265(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.7830(18) _cell_length_b 13.245(2) _cell_length_c 15.8627(18) _cell_measurement_reflns_used 5110 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.56 _cell_measurement_theta_min 2.32 _cell_volume 2468.8(6) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_unetI/netI 0.0552 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 13308 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.009 _diffrn_reflns_theta_max 25.009 _diffrn_reflns_theta_min 2.235 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6294 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_density_diffrn 1.240 _exptl_crystal_F_000 952 _exptl_crystal_size_max 0.270 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.220 _platon_squeeze_void_content 1 _refine_diff_density_max 0.282 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.059 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 299 _refine_ls_number_reflns 4338 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0473 _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^)+(0.0679P)^2^+0.9205P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1283 _refine_ls_wR_factor_ref 0.1341 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 3360 _reflns_number_total 4338 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6cc00525j2.cif _cod_data_source_block 4b _cod_depositor_comments ; 2017-12-13 Z value and formula fixed to values more according to usual chemical conventions. miguel ; _cod_original_formula_sum 'C3.12 H2.12 Cl0.12 N0.25 O0.62' _cod_original_formula_weight 57.61 _cod_original_formula_units_Z 32 _cod_database_code 7119079 _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 0.950 _shelx_estimated_absorpt_t_max 0.959 _platon_squeeze_void_probe_radius 1.20 _shelx_res_file ; 20151120yzu1_0m_sqd.res created by SHELXL-2014/7 TITL 20151120YZU1_0m in P2(1)/n CELL 0.71073 11.78300 13.24500 15.86270 90.0000 94.2650 90.0000 ZERR 32.00 0.00180 0.00200 0.00180 0.0000 0.0039 0.0000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O Cl UNIT 100 68 8 20 4 L.S. 8 OMIT -3 50.02 ACTA BOND $H CONF HTAB SIZE .27 .25 .22 FMAP 2 PLAN 20 TEMP 23.000 WGHT 0.067900 0.920500 FVAR 1.75910 MOLE 1 C1 1 0.898848 0.277430 0.711139 11.00000 0.01613 0.01718 = 0.02309 -0.00216 -0.00055 -0.00056 AFIX 43 H1 2 0.954763 0.295463 0.675563 11.00000 -1.20000 AFIX 0 C2 1 0.899720 0.318599 0.790750 11.00000 0.01873 0.02434 = 0.02488 -0.00928 0.00138 -0.00299 AFIX 43 H2 2 0.956417 0.363986 0.809284 11.00000 -1.20000 AFIX 0 C3 1 0.815713 0.292103 0.843167 11.00000 0.02837 0.02135 = 0.01705 -0.00577 0.00171 0.00096 AFIX 43 H3 2 0.814821 0.320095 0.896882 11.00000 -1.20000 AFIX 0 C4 1 0.733356 0.223647 0.814688 11.00000 0.02603 0.02100 = 0.01770 0.00051 0.00639 -0.00226 AFIX 43 H4 2 0.676661 0.204728 0.849292 11.00000 -1.20000 AFIX 0 C5 1 0.735512 0.183429 0.734693 11.00000 0.01970 0.01514 = 0.01667 0.00198 0.00007 -0.00477 AFIX 43 H5 2 0.680285 0.137061 0.715372 11.00000 -1.20000 AFIX 0 C6 1 0.820487 0.168779 0.597337 11.00000 0.01345 0.01615 = 0.01108 -0.00242 0.00243 -0.00238 AFIX 13 H6 2 0.868655 0.214493 0.567033 11.00000 -1.20000 AFIX 0 C7 1 0.880079 0.066580 0.599677 11.00000 0.01214 0.01717 = 0.01871 0.00031 0.00115 -0.00105 C8 1 1.008588 -0.043371 0.673225 11.00000 0.04182 0.02935 = 0.02649 -0.00375 -0.00881 0.01999 AFIX 137 H8A 2 0.957394 -0.099603 0.665932 11.00000 -1.50000 H8B 2 1.051853 -0.049052 0.726732 11.00000 -1.50000 H8C 2 1.059327 -0.043184 0.628594 11.00000 -1.50000 AFIX 0 C9 1 0.702185 0.165750 0.544659 11.00000 0.01238 0.01138 = 0.01339 0.00001 0.00062 -0.00091 C10 1 0.642118 0.062214 0.556161 11.00000 0.01258 0.00983 = 0.02030 0.00115 0.00102 0.00026 C11 1 0.666160 0.076350 0.415464 11.00000 0.00924 0.01422 = 0.01856 -0.00023 0.00223 0.00313 C12 1 0.659044 0.057773 0.329754 11.00000 0.01335 0.01536 = 0.02325 -0.00567 0.00013 0.00029 AFIX 43 H12 2 0.624298 -0.000451 0.307555 11.00000 -1.20000 AFIX 0 C13 1 0.705228 0.128466 0.277510 11.00000 0.01948 0.02384 = 0.01399 -0.00251 0.00410 0.00358 AFIX 43 H13 2 0.699897 0.118993 0.219257 11.00000 -1.20000 AFIX 0 C14 1 0.759531 0.213559 0.312594 11.00000 0.02363 0.01694 = 0.01955 0.00408 0.00778 0.00027 C15 1 0.766917 0.232866 0.398697 11.00000 0.01736 0.01266 = 0.02025 -0.00186 0.00361 -0.00038 AFIX 43 H15 2 0.802610 0.290625 0.420975 11.00000 -1.20000 AFIX 0 C16 1 0.719009 0.162699 0.450295 11.00000 0.01121 0.01239 = 0.01640 -0.00025 0.00010 0.00328 C17 1 0.627443 0.253388 0.565253 11.00000 0.01428 0.01358 = 0.01144 0.00078 0.00156 0.00112 C18 1 0.506909 0.253130 0.564043 11.00000 0.01686 0.01422 = 0.00746 -0.00079 0.00102 -0.00110 C19 1 0.470478 0.359213 0.584025 11.00000 0.01767 0.01445 = 0.01089 0.00020 0.00215 0.00092 C20 1 0.364869 0.399198 0.592028 11.00000 0.01669 0.01744 = 0.01745 -0.00044 0.00114 -0.00234 AFIX 43 H20 2 0.300105 0.358934 0.586116 11.00000 -1.20000 AFIX 0 C21 1 0.356916 0.503425 0.609533 11.00000 0.01876 0.02183 = 0.01617 -0.00017 0.00398 0.00516 AFIX 43 H21 2 0.285992 0.532253 0.615499 11.00000 -1.20000 AFIX 0 C22 1 0.453300 0.562985 0.617886 11.00000 0.02846 0.01254 = 0.01932 -0.00064 0.00360 0.00398 AFIX 43 H22 2 0.446598 0.631395 0.629753 11.00000 -1.20000 AFIX 0 C23 1 0.561213 0.521452 0.608673 11.00000 0.02182 0.01193 = 0.01793 0.00155 -0.00024 -0.00090 AFIX 43 H23 2 0.626214 0.561476 0.613668 11.00000 -1.20000 AFIX 0 C24 1 0.568050 0.419839 0.592041 11.00000 0.01841 0.01336 = 0.01295 0.00142 0.00030 0.00036 C25 1 0.668790 0.354020 0.576163 11.00000 0.01570 0.01159 = 0.01228 -0.00082 -0.00001 0.00037 CL1 5 0.816604 0.300335 0.244479 11.00000 0.05967 0.02879 = 0.02068 0.00191 0.01244 -0.01776 N1 3 0.622069 0.018706 0.479369 11.00000 0.01419 0.01067 = 0.01856 0.00027 0.00192 -0.00286 AFIX 3 H1A 2 0.590949 -0.044931 0.473355 11.00000 -1.20000 AFIX 0 N2 3 0.817221 0.211014 0.684470 11.00000 0.01320 0.01224 = 0.01397 -0.00092 0.00039 0.00103 O1 4 0.943523 0.050448 0.670817 11.00000 0.02767 0.02491 = 0.01984 -0.00315 -0.00657 0.01397 O2 4 0.872146 0.009478 0.540456 11.00000 0.02744 0.02200 = 0.02777 -0.01020 -0.00683 0.00935 O3 4 0.437882 0.182547 0.548013 11.00000 0.01494 0.01307 = 0.02539 -0.00335 0.00199 -0.00296 O4 4 0.768826 0.385696 0.572724 11.00000 0.01224 0.01420 = 0.02914 0.00190 0.00013 -0.00170 O5 4 0.618476 0.025375 0.623613 11.00000 0.02176 0.01354 = 0.01833 0.00277 0.00051 -0.00492 HKLF 4 REM 20151120YZU1_0m in P2(1)/n REM R1 = 0.0473 for 3360 Fo > 4sig(Fo) and 0.0621 for all 4338 data REM 299 parameters refined using 0 restraints END WGHT 0.0663 0.8337 REM Instructions for potential hydrogen bonds EQIV $1 -x+3/2, y+1/2, -z+3/2 HTAB C2 O5_$1 HTAB C5 O5 EQIV $2 -x+3/2, y-1/2, -z+1/2 HTAB C12 Cl1_$2 EQIV $3 -x+1, -y, -z+1 HTAB N1 O3_$3 REM Highest difference peak 0.282, deepest hole -0.260, 1-sigma level 0.059 Q1 1 0.8806 0.2888 0.2805 11.00000 0.05 0.28 Q2 1 0.8180 0.4816 0.5672 11.00000 0.05 0.26 Q3 1 0.7400 0.3579 0.1979 11.00000 0.05 0.24 Q4 1 0.7971 0.3826 0.6235 11.00000 0.05 0.23 Q5 1 0.4189 0.3786 0.5608 11.00000 0.05 0.22 Q6 1 0.6106 0.3938 0.5816 11.00000 0.05 0.22 Q7 1 0.6842 0.1147 0.5574 11.00000 0.05 0.21 Q8 1 0.6637 0.2111 0.5588 11.00000 0.05 0.21 Q9 1 0.9223 0.0803 0.7179 11.00000 0.05 0.21 Q10 1 0.7248 0.3798 0.6204 11.00000 0.05 0.21 Q11 1 0.5963 -0.0797 0.2846 11.00000 0.05 0.20 Q12 1 0.4813 0.3064 0.5689 11.00000 0.05 0.20 Q13 1 0.4176 0.3660 0.6271 11.00000 0.05 0.20 Q14 1 0.5835 -0.0942 0.2983 11.00000 0.05 0.20 Q15 1 0.5690 0.4620 0.5875 11.00000 0.05 0.20 Q16 1 0.5019 0.6623 0.5623 11.00000 0.05 0.20 Q17 1 0.6183 0.1947 0.6526 11.00000 0.05 0.20 Q18 1 0.7334 0.1624 0.5012 11.00000 0.05 0.20 Q19 1 0.7518 0.1668 0.5741 11.00000 0.05 0.20 Q20 1 0.9017 0.2400 0.9236 11.00000 0.05 0.20 ; _shelx_res_checksum 15505 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 C1 C 0.8988(2) 0.27743(18) 0.71114(16) 0.0189(5) Uani 1 1 d . . . . . H1 H 0.9548 0.2955 0.6756 0.023 Uiso 1 1 calc R U . . . C2 C 0.8997(2) 0.31860(19) 0.79075(16) 0.0227(6) Uani 1 1 d . . . . . H2 H 0.9564 0.3640 0.8093 0.027 Uiso 1 1 calc R U . . . C3 C 0.8157(2) 0.29210(19) 0.84317(16) 0.0223(6) Uani 1 1 d . . . . . H3 H 0.8148 0.3201 0.8969 0.027 Uiso 1 1 calc R U . . . C4 C 0.7334(2) 0.22365(19) 0.81469(16) 0.0213(6) Uani 1 1 d . . . . . H4 H 0.6767 0.2047 0.8493 0.026 Uiso 1 1 calc R U . . . C5 C 0.7355(2) 0.18343(18) 0.73469(15) 0.0172(5) Uani 1 1 d . . . . . H5 H 0.6803 0.1371 0.7154 0.021 Uiso 1 1 calc R U . . . C6 C 0.82049(19) 0.16878(17) 0.59734(14) 0.0135(5) Uani 1 1 d . . . . . H6 H 0.8687 0.2145 0.5670 0.016 Uiso 1 1 calc R U . . . C7 C 0.88008(19) 0.06658(18) 0.59968(15) 0.0160(5) Uani 1 1 d . . . . . C8 C 1.0086(3) -0.0434(2) 0.67322(18) 0.0331(7) Uani 1 1 d . . . . . H8A H 0.9574 -0.0996 0.6659 0.050 Uiso 1 1 calc R U . . . H8B H 1.0519 -0.0491 0.7267 0.050 Uiso 1 1 calc R U . . . H8C H 1.0593 -0.0432 0.6286 0.050 Uiso 1 1 calc R U . . . C9 C 0.70219(18) 0.16575(17) 0.54466(14) 0.0124(5) Uani 1 1 d . . . . . C10 C 0.64212(19) 0.06221(17) 0.55616(15) 0.0142(5) Uani 1 1 d . . . . . C11 C 0.66616(18) 0.07635(17) 0.41546(15) 0.0140(5) Uani 1 1 d . . . . . C12 C 0.6590(2) 0.05777(18) 0.32975(15) 0.0174(5) Uani 1 1 d . . . . . H12 H 0.6243 -0.0005 0.3076 0.021 Uiso 1 1 calc R U . . . C13 C 0.7052(2) 0.12847(19) 0.27751(15) 0.0190(5) Uani 1 1 d . . . . . H13 H 0.6999 0.1190 0.2193 0.023 Uiso 1 1 calc R U . . . C14 C 0.7595(2) 0.21356(18) 0.31259(15) 0.0197(5) Uani 1 1 d . . . . . C15 C 0.7669(2) 0.23287(18) 0.39870(15) 0.0166(5) Uani 1 1 d . . . . . H15 H 0.8026 0.2906 0.4210 0.020 Uiso 1 1 calc R U . . . C16 C 0.71901(18) 0.16270(17) 0.45030(14) 0.0134(5) Uani 1 1 d . . . . . C17 C 0.62744(19) 0.25339(17) 0.56525(14) 0.0131(5) Uani 1 1 d . . . . . C18 C 0.50691(19) 0.25313(17) 0.56404(13) 0.0128(5) Uani 1 1 d . . . . . C19 C 0.47048(19) 0.35921(17) 0.58402(14) 0.0143(5) Uani 1 1 d . . . . . C20 C 0.3649(2) 0.39920(18) 0.59203(15) 0.0172(5) Uani 1 1 d . . . . . H20 H 0.3001 0.3589 0.5861 0.021 Uiso 1 1 calc R U . . . C21 C 0.3569(2) 0.50342(19) 0.60953(15) 0.0188(5) Uani 1 1 d . . . . . H21 H 0.2860 0.5323 0.6155 0.023 Uiso 1 1 calc R U . . . C22 C 0.4533(2) 0.56298(18) 0.61789(15) 0.0200(5) Uani 1 1 d . . . . . H22 H 0.4466 0.6314 0.6298 0.024 Uiso 1 1 calc R U . . . C23 C 0.5612(2) 0.52145(17) 0.60867(15) 0.0173(5) Uani 1 1 d . . . . . H23 H 0.6262 0.5615 0.6137 0.021 Uiso 1 1 calc R U . . . C24 C 0.5681(2) 0.41984(17) 0.59204(14) 0.0150(5) Uani 1 1 d . . . . . C25 C 0.66879(19) 0.35402(17) 0.57616(14) 0.0132(5) Uani 1 1 d . . . . . Cl1 Cl 0.81660(7) 0.30034(5) 0.24448(4) 0.0359(2) Uani 1 1 d . . . . . N1 N 0.62207(16) 0.01871(14) 0.47937(12) 0.0144(4) Uani 1 1 d . . . . . H1A H 0.5909 -0.0449 0.4734 0.017 Uiso 1 1 d R U . . . N2 N 0.81722(16) 0.21101(14) 0.68447(12) 0.0132(4) Uani 1 1 d . . . . . O1 O 0.94352(15) 0.05045(13) 0.67082(11) 0.0246(4) Uani 1 1 d . . . . . O2 O 0.87215(15) 0.00948(13) 0.54046(11) 0.0262(4) Uani 1 1 d . . . . . O3 O 0.43788(13) 0.18255(12) 0.54801(10) 0.0178(4) Uani 1 1 d . . . . . O4 O 0.76883(13) 0.38570(12) 0.57272(10) 0.0186(4) Uani 1 1 d . . . . . O5 O 0.61848(14) 0.02538(12) 0.62361(10) 0.0179(4) Uani 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 C1 0.0161(12) 0.0172(13) 0.0231(14) -0.0022(10) -0.0005(10) -0.0006(10) C2 0.0187(13) 0.0243(14) 0.0249(15) -0.0093(10) 0.0014(10) -0.0030(10) C3 0.0284(14) 0.0213(13) 0.0171(14) -0.0058(10) 0.0017(10) 0.0010(11) C4 0.0260(14) 0.0210(13) 0.0177(14) 0.0005(10) 0.0064(10) -0.0023(11) C5 0.0197(12) 0.0151(12) 0.0167(13) 0.0020(9) 0.0001(10) -0.0048(10) C6 0.0135(11) 0.0161(12) 0.0111(12) -0.0024(9) 0.0024(9) -0.0024(9) C7 0.0121(11) 0.0172(12) 0.0187(13) 0.0003(10) 0.0011(9) -0.0010(9) C8 0.0418(17) 0.0293(15) 0.0265(16) -0.0037(12) -0.0088(12) 0.0200(13) C9 0.0124(11) 0.0114(11) 0.0134(12) 0.0000(9) 0.0006(9) -0.0009(9) C10 0.0126(12) 0.0098(11) 0.0203(14) 0.0011(9) 0.0010(9) 0.0003(9) C11 0.0092(11) 0.0142(12) 0.0186(13) -0.0002(9) 0.0022(9) 0.0031(9) C12 0.0134(12) 0.0154(12) 0.0232(14) -0.0057(10) 0.0001(10) 0.0003(9) C13 0.0195(12) 0.0238(13) 0.0140(13) -0.0025(10) 0.0041(9) 0.0036(10) C14 0.0236(13) 0.0169(13) 0.0195(14) 0.0041(10) 0.0078(10) 0.0003(10) C15 0.0174(12) 0.0127(12) 0.0203(14) -0.0019(9) 0.0036(9) -0.0004(9) C16 0.0112(11) 0.0124(11) 0.0164(13) -0.0003(9) 0.0001(9) 0.0033(9) C17 0.0143(11) 0.0136(12) 0.0114(12) 0.0008(8) 0.0016(9) 0.0011(9) C18 0.0169(12) 0.0142(12) 0.0075(12) -0.0008(8) 0.0010(9) -0.0011(9) C19 0.0177(12) 0.0144(12) 0.0109(12) 0.0002(9) 0.0022(9) 0.0009(10) C20 0.0167(12) 0.0174(12) 0.0174(13) -0.0004(9) 0.0011(9) -0.0023(10) C21 0.0188(12) 0.0218(13) 0.0162(13) -0.0002(9) 0.0040(10) 0.0052(10) C22 0.0285(14) 0.0125(12) 0.0193(14) -0.0006(9) 0.0036(10) 0.0040(10) C23 0.0218(12) 0.0119(12) 0.0179(13) 0.0016(9) -0.0002(10) -0.0009(10) C24 0.0184(12) 0.0134(12) 0.0130(12) 0.0014(9) 0.0003(9) 0.0004(9) C25 0.0157(12) 0.0116(11) 0.0123(12) -0.0008(9) 0.0000(9) 0.0004(9) Cl1 0.0597(5) 0.0288(4) 0.0207(4) 0.0019(3) 0.0124(3) -0.0178(3) N1 0.0142(10) 0.0107(10) 0.0186(11) 0.0003(8) 0.0019(8) -0.0029(8) N2 0.0132(10) 0.0122(10) 0.0140(10) -0.0009(7) 0.0004(8) 0.0010(8) O1 0.0277(10) 0.0249(10) 0.0198(10) -0.0031(7) -0.0066(7) 0.0140(8) O2 0.0274(10) 0.0220(10) 0.0278(11) -0.0102(8) -0.0068(8) 0.0093(8) O3 0.0149(8) 0.0131(8) 0.0254(10) -0.0034(7) 0.0020(7) -0.0030(7) O4 0.0122(8) 0.0142(8) 0.0291(10) 0.0019(7) 0.0001(7) -0.0017(7) O5 0.0218(9) 0.0135(8) 0.0183(10) 0.0028(7) 0.0005(7) -0.0049(7) 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' Cl Cl 0.1484 0.1585 '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 N2 C1 C2 120.2(2) . . N2 C1 H1 119.9 . . C2 C1 H1 119.9 . . C1 C2 C3 119.6(2) . . C1 C2 H2 120.2 . . C3 C2 H2 120.2 . . C4 C3 C2 119.1(2) . . C4 C3 H3 120.4 . . C2 C3 H3 120.4 . . C5 C4 C3 119.7(2) . . C5 C4 H4 120.2 . . C3 C4 H4 120.2 . . N2 C5 C4 120.2(2) . . N2 C5 H5 119.9 . . C4 C5 H5 119.9 . . N2 C6 C7 110.70(18) . . N2 C6 C9 114.74(18) . . C7 C6 C9 112.28(18) . . N2 C6 H6 106.1 . . C7 C6 H6 106.1 . . C9 C6 H6 106.1 . . O2 C7 O1 124.7(2) . . O2 C7 C6 122.0(2) . . O1 C7 C6 113.21(19) . . O1 C8 H8A 109.5 . . O1 C8 H8B 109.5 . . H8A C8 H8B 109.5 . . O1 C8 H8C 109.5 . . H8A C8 H8C 109.5 . . H8B C8 H8C 109.5 . . C17 C9 C16 110.72(18) . . C17 C9 C10 111.97(18) . . C16 C9 C10 100.64(17) . . C17 C9 C6 111.99(18) . . C16 C9 C6 110.35(18) . . C10 C9 C6 110.64(18) . . O5 C10 N1 125.5(2) . . O5 C10 C9 125.9(2) . . N1 C10 C9 108.64(19) . . C12 C11 C16 122.0(2) . . C12 C11 N1 128.2(2) . . C16 C11 N1 109.8(2) . . C11 C12 C13 118.1(2) . . C11 C12 H12 121.0 . . C13 C12 H12 121.0 . . C12 C13 C14 119.8(2) . . C12 C13 H13 120.1 . . C14 C13 H13 120.1 . . C15 C14 C13 122.5(2) . . C15 C14 Cl1 119.31(19) . . C13 C14 Cl1 118.19(19) . . C16 C15 C14 117.4(2) . . C16 C15 H15 121.3 . . C14 C15 H15 121.3 . . C15 C16 C11 120.3(2) . . C15 C16 C9 130.6(2) . . C11 C16 C9 108.87(19) . . C18 C17 C25 109.67(19) . . C18 C17 C9 126.5(2) . . C25 C17 C9 123.13(19) . . O3 C18 C17 129.7(2) . . O3 C18 C19 123.1(2) . . C17 C18 C19 107.15(19) . . C20 C19 C24 121.1(2) . . C20 C19 C18 130.9(2) . . C24 C19 C18 107.96(19) . . C19 C20 C21 118.1(2) . . C19 C20 H20 120.9 . . C21 C20 H20 120.9 . . C22 C21 C20 120.7(2) . . C22 C21 H21 119.6 . . C20 C21 H21 119.6 . . C21 C22 C23 120.7(2) . . C21 C22 H22 119.6 . . C23 C22 H22 119.6 . . C24 C23 C22 118.1(2) . . C24 C23 H23 121.0 . . C22 C23 H23 121.0 . . C23 C24 C19 121.3(2) . . C23 C24 C25 131.0(2) . . C19 C24 C25 107.72(19) . . O4 C25 C17 128.3(2) . . O4 C25 C24 124.5(2) . . C17 C25 C24 107.13(19) . . C10 N1 C11 111.75(19) . . C10 N1 H1A 121.6 . . C11 N1 H1A 126.2 . . C5 N2 C1 121.1(2) . . C5 N2 C6 121.00(19) . . C1 N2 C6 117.89(19) . . C7 O1 C8 114.97(19) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 N2 1.348(3) . C1 C2 1.375(4) . C1 H1 0.9300 . C2 C3 1.384(4) . C2 H2 0.9300 . C3 C4 1.379(4) . C3 H3 0.9300 . C4 C5 1.378(4) . C4 H4 0.9300 . C5 N2 1.345(3) . C5 H5 0.9300 . C6 N2 1.494(3) . C6 C7 1.524(3) . C6 C9 1.572(3) . C6 H6 0.9800 . C7 O2 1.204(3) . C7 O1 1.324(3) . C8 O1 1.459(3) . C8 H8A 0.9600 . C8 H8B 0.9600 . C8 H8C 0.9600 . C9 C17 1.507(3) . C9 C16 1.525(3) . C9 C10 1.560(3) . C10 O5 1.227(3) . C10 N1 1.352(3) . C11 C12 1.378(3) . C11 C16 1.396(3) . C11 N1 1.400(3) . C12 C13 1.388(3) . C12 H12 0.9300 . C13 C14 1.392(3) . C13 H13 0.9300 . C14 C15 1.386(3) . C14 Cl1 1.746(2) . C15 C16 1.386(3) . C15 H15 0.9300 . C17 C18 1.419(3) . C17 C25 1.425(3) . C18 O3 1.253(3) . C18 C19 1.510(3) . C19 C20 1.367(3) . C19 C24 1.400(3) . C20 C21 1.413(3) . C20 H20 0.9300 . C21 C22 1.381(4) . C21 H21 0.9300 . C22 C23 1.403(3) . C22 H22 0.9300 . C23 C24 1.375(3) . C23 H23 0.9300 . C24 C25 1.509(3) . C25 O4 1.256(3) . N1 H1A 0.9213 . 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 N2 C1 C2 C3 -0.5(4) . . . . C1 C2 C3 C4 0.8(4) . . . . C2 C3 C4 C5 -0.4(4) . . . . C3 C4 C5 N2 -0.2(4) . . . . N2 C6 C7 O2 164.3(2) . . . . C9 C6 C7 O2 34.6(3) . . . . N2 C6 C7 O1 -18.4(3) . . . . C9 C6 C7 O1 -148.1(2) . . . . N2 C6 C9 C17 33.6(3) . . . . C7 C6 C9 C17 161.18(19) . . . . N2 C6 C9 C16 157.46(18) . . . . C7 C6 C9 C16 -75.0(2) . . . . N2 C6 C9 C10 -92.0(2) . . . . C7 C6 C9 C10 35.5(2) . . . . C17 C9 C10 O5 -68.4(3) . . . . C16 C9 C10 O5 173.9(2) . . . . C6 C9 C10 O5 57.3(3) . . . . C17 C9 C10 N1 112.6(2) . . . . C16 C9 C10 N1 -5.0(2) . . . . C6 C9 C10 N1 -121.7(2) . . . . C16 C11 C12 C13 -0.7(3) . . . . N1 C11 C12 C13 177.1(2) . . . . C11 C12 C13 C14 1.8(3) . . . . C12 C13 C14 C15 -2.0(4) . . . . C12 C13 C14 Cl1 179.88(18) . . . . C13 C14 C15 C16 0.9(4) . . . . Cl1 C14 C15 C16 179.07(18) . . . . C14 C15 C16 C11 0.2(3) . . . . C14 C15 C16 C9 -173.3(2) . . . . C12 C11 C16 C15 -0.3(3) . . . . N1 C11 C16 C15 -178.5(2) . . . . C12 C11 C16 C9 174.5(2) . . . . N1 C11 C16 C9 -3.7(2) . . . . C17 C9 C16 C15 60.7(3) . . . . C10 C9 C16 C15 179.2(2) . . . . C6 C9 C16 C15 -63.9(3) . . . . C17 C9 C16 C11 -113.4(2) . . . . C10 C9 C16 C11 5.2(2) . . . . C6 C9 C16 C11 122.0(2) . . . . C16 C9 C17 C18 88.4(3) . . . . C10 C9 C17 C18 -23.0(3) . . . . C6 C9 C17 C18 -148.0(2) . . . . C16 C9 C17 C25 -81.4(3) . . . . C10 C9 C17 C25 167.2(2) . . . . C6 C9 C17 C25 42.3(3) . . . . C25 C17 C18 O3 172.5(2) . . . . C9 C17 C18 O3 1.6(4) . . . . C25 C17 C18 C19 -5.8(2) . . . . C9 C17 C18 C19 -176.7(2) . . . . O3 C18 C19 C20 2.7(4) . . . . C17 C18 C19 C20 -178.8(2) . . . . O3 C18 C19 C24 -175.4(2) . . . . C17 C18 C19 C24 3.0(2) . . . . C24 C19 C20 C21 -0.7(3) . . . . C18 C19 C20 C21 -178.6(2) . . . . C19 C20 C21 C22 0.3(3) . . . . C20 C21 C22 C23 0.4(4) . . . . C21 C22 C23 C24 -0.7(3) . . . . C22 C23 C24 C19 0.3(3) . . . . C22 C23 C24 C25 177.7(2) . . . . C20 C19 C24 C23 0.4(3) . . . . C18 C19 C24 C23 178.7(2) . . . . C20 C19 C24 C25 -177.6(2) . . . . C18 C19 C24 C25 0.8(2) . . . . C18 C17 C25 O4 -172.9(2) . . . . C9 C17 C25 O4 -1.6(4) . . . . C18 C17 C25 C24 6.3(2) . . . . C9 C17 C25 C24 177.54(19) . . . . C23 C24 C25 O4 -2.7(4) . . . . C19 C24 C25 O4 175.0(2) . . . . C23 C24 C25 C17 178.0(2) . . . . C19 C24 C25 C17 -4.3(2) . . . . O5 C10 N1 C11 -175.7(2) . . . . C9 C10 N1 C11 3.2(2) . . . . C12 C11 N1 C10 -177.8(2) . . . . C16 C11 N1 C10 0.3(3) . . . . C4 C5 N2 C1 0.6(3) . . . . C4 C5 N2 C6 -179.6(2) . . . . C2 C1 N2 C5 -0.2(3) . . . . C2 C1 N2 C6 180.0(2) . . . . C7 C6 N2 C5 -83.6(2) . . . . C9 C6 N2 C5 44.7(3) . . . . C7 C6 N2 C1 96.2(2) . . . . C9 C6 N2 C1 -135.4(2) . . . . O2 C7 O1 C8 1.5(4) . . . . C6 C7 O1 C8 -175.8(2) . . . .