#------------------------------------------------------------------------------ #$Date: 2020-07-06 06:48:03 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253986 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157511.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_7157511 loop_ _publ_author_name 'Singh, Manpreet' 'Vaishali, ?' 'Paul, Avijit Kumar' 'Singh, Virender' _publ_section_title ; Isatin as a 2-aminobenzaldehyde surrogate: transition metal-free efficient synthesis of 2-(2'-aminophenyl)benzothiazole derivatives. ; _journal_issue 23 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4459 _journal_paper_doi 10.1039/d0ob00888e _journal_volume 18 _journal_year 2020 _chemical_formula_sum 'C28 H20 N4 O4 S2' _chemical_formula_weight 540.60 _chemical_name_common NRVS1 _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-01-30 deposited with the CCDC. 2020-05-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.677(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.7318(10) _cell_length_b 9.1027(7) _cell_length_c 20.8094(15) _cell_measurement_reflns_used 4170 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 24.997 _cell_measurement_theta_min 1.610 _cell_volume 2395.3(3) _computing_cell_refinement 'SAINT V8.37A (Bruker, 2016)' _computing_data_collection 'Apex3 v2016.9-0 (Bruker, 2016)' _computing_data_reduction 'SAINT V8.37A (Bruker, 2016)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker AXS D8 Quest CMOS diffractometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0645 _diffrn_reflns_av_unetI/netI 0.0435 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 23759 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 1.610 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.7050 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2016/2)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'Block like' _exptl_crystal_F_000 1120 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.255 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 343 _refine_ls_number_reflns 4170 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0415 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0618P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1041 _refine_ls_wR_factor_ref 0.1191 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2928 _reflns_number_total 4170 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00888e2.cif _cod_data_source_block shelx _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7157511.cif. ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7157511 _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 NRVS1_0m_a.res in P2(1)/c shelx.res created by SHELXL-2018/3 at 22:54:21 on 25-Jan-2020 CELL 0.71073 12.7318 9.1027 20.8094 90.000 96.677 90.000 ZERR 4.00 0.0010 0.0007 0.0015 0.000 0.002 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 112 80 16 16 8 MERG 2 OMIT 0.00 50.00 OMIT -2 0 2 OMIT 0 0 2 OMIT -1 0 2 OMIT 1 1 0 OMIT 2 2 1 OMIT 0 2 4 OMIT 1 1 1 OMIT 2 1 12 OMIT 2 0 0 OMIT -2 1 1 OMIT -6 1 8 OMIT -4 0 8 OMIT -2 0 4 OMIT 2 2 3 OMIT 1 1 7 OMIT 5 2 4 OMIT -2 3 5 OMIT -7 0 8 OMIT 2 3 1 OMIT 2 2 9 OMIT -6 4 15 OMIT -6 3 3 OMIT -6 1 6 OMIT -7 2 10 OMIT -4 3 4 OMIT -5 2 10 OMIT -5 6 7 OMIT 3 2 6 OMIT 1 2 7 OMIT -2 8 10 OMIT -1 4 6 OMIT 3 1 7 OMIT 5 3 0 OMIT 3 3 19 OMIT 8 7 12 OMIT 5 4 0 OMIT -2 2 4 OMIT -1 2 4 OMIT -2 1 4 OMIT -7 1 16 OMIT -11 2 9 OMIT -4 2 10 OMIT 1 1 4 OMIT 0 3 10 OMIT -5 1 7 OMIT -6 6 6 OMIT -2 4 16 OMIT -3 2 4 OMIT 3 1 5 OMIT -5 5 16 FMAP 2 PLAN 20 ACTA BOND $H L.S. 10 TEMP 23.00 WGHT 0.061800 FVAR 0.43088 S2 5 -0.069757 0.392894 0.593307 11.00000 0.04220 0.05974 = 0.05544 -0.00373 0.01139 0.00066 S1 5 0.651297 0.420429 0.538217 11.00000 0.04566 0.06115 = 0.05068 0.00164 0.01424 0.00111 O1 4 0.436817 0.063596 0.373348 11.00000 0.06973 0.07782 = 0.04445 -0.00996 0.00907 0.00164 O2 4 0.313021 0.024334 0.444195 11.00000 0.06200 0.07798 = 0.05813 -0.01255 0.00849 -0.00830 O3 4 0.027398 0.044009 0.375240 11.00000 0.08416 0.08406 = 0.06285 -0.01953 0.01296 0.00802 N2 3 0.502037 0.347319 0.606364 11.00000 0.04193 0.05691 = 0.04157 -0.00026 0.00777 0.00519 N4 3 0.117873 0.376281 0.558349 11.00000 0.04712 0.05365 = 0.05178 0.00237 0.01069 0.00195 N1 3 0.508051 0.421597 0.734278 11.00000 0.06867 0.10089 = 0.04373 -0.01033 0.01709 -0.01642 AFIX 93 H1A 2 0.485199 0.419449 0.771565 11.00000 -1.20000 H1B 2 0.479157 0.366976 0.703433 11.00000 -1.20000 AFIX 0 N3 3 0.288740 0.516094 0.622841 11.00000 0.04302 0.08558 = 0.07879 -0.00036 0.01176 -0.00490 AFIX 93 H3A 2 0.354644 0.539094 0.629227 11.00000 -1.20000 H3B 2 0.266020 0.459260 0.591237 11.00000 -1.20000 AFIX 0 O4 4 -0.147801 0.035497 0.395484 11.00000 0.07713 0.08065 = 0.07424 -0.02491 -0.00192 -0.00175 C1 1 0.589758 0.511233 0.724104 11.00000 0.04940 0.06019 = 0.04856 -0.00304 0.00200 0.01464 C20 1 0.110497 0.536407 0.652888 11.00000 0.04791 0.04667 = 0.04585 0.00861 0.00590 0.00022 C13 1 0.395088 0.181843 0.531379 11.00000 0.04432 0.06035 = 0.04351 0.00323 0.00971 0.00092 AFIX 43 H13 2 0.344690 0.164457 0.559441 11.00000 -1.20000 AFIX 0 C8 1 0.481409 0.274277 0.547645 11.00000 0.04261 0.05167 = 0.03790 0.00481 0.00703 0.00869 C12 1 0.389318 0.118624 0.471722 11.00000 0.04360 0.05175 = 0.04564 0.00289 0.00140 0.00352 C15 1 0.220344 0.569685 0.662783 11.00000 0.04519 0.05134 = 0.05627 0.01519 0.00404 0.00027 C6 1 0.630183 0.518512 0.663702 11.00000 0.04250 0.04578 = 0.05305 0.00134 0.00279 0.01021 C7 1 0.587245 0.428044 0.608564 11.00000 0.04180 0.04705 = 0.04525 0.00651 0.00620 0.01289 C9 1 0.555538 0.300022 0.504081 11.00000 0.04127 0.05001 = 0.04255 0.00579 0.00921 0.00856 C21 1 0.065734 0.437931 0.601128 11.00000 0.04440 0.04501 = 0.04882 0.00923 0.00946 0.00403 C27 1 -0.128486 0.200044 0.489246 11.00000 0.05167 0.05527 = 0.05929 0.00010 0.00410 0.00295 AFIX 43 H27 2 -0.198848 0.196169 0.497134 11.00000 -1.20000 AFIX 0 C19 1 0.044866 0.598937 0.694259 11.00000 0.05664 0.06240 = 0.05737 -0.00282 0.01124 -0.00523 AFIX 43 H19 2 -0.027066 0.577810 0.688046 11.00000 -1.20000 AFIX 0 C11 1 0.463464 0.142995 0.429248 11.00000 0.05745 0.05419 = 0.03446 0.00140 0.00470 0.01136 C10 1 0.547788 0.232746 0.442968 11.00000 0.05219 0.06242 = 0.04000 0.00664 0.01335 0.00740 AFIX 43 H10 2 0.597049 0.248740 0.414034 11.00000 -1.20000 AFIX 0 C22 1 -0.052496 0.283685 0.527262 11.00000 0.04696 0.04698 = 0.04957 0.00722 0.00813 0.00545 C5 1 0.714807 0.613712 0.657421 11.00000 0.05093 0.05244 = 0.06862 0.00116 0.00408 0.00874 AFIX 43 H5 2 0.742153 0.619040 0.617945 11.00000 -1.20000 AFIX 0 C18 1 0.082735 0.691377 0.744289 11.00000 0.07566 0.06820 = 0.06010 -0.00883 0.01248 -0.00392 AFIX 43 H18 2 0.037149 0.732463 0.771161 11.00000 -1.20000 AFIX 0 C23 1 0.053596 0.289215 0.515998 11.00000 0.05066 0.04872 = 0.04791 0.00692 0.00957 0.00280 C24 1 0.088859 0.208834 0.464504 11.00000 0.05309 0.06399 = 0.05630 0.00238 0.01367 0.00991 AFIX 43 H24 2 0.159048 0.210020 0.456162 11.00000 -1.20000 AFIX 0 C2 1 0.636513 0.599886 0.774418 11.00000 0.06717 0.07862 = 0.05634 -0.01585 -0.00003 0.01466 AFIX 43 H2 2 0.611109 0.595586 0.814509 11.00000 -1.20000 AFIX 0 C25 1 0.013821 0.129968 0.428092 11.00000 0.07036 0.05146 = 0.04722 -0.00093 0.00949 0.00951 C26 1 -0.091954 0.125398 0.440254 11.00000 0.06181 0.05117 = 0.05059 0.00180 -0.00155 0.00389 C4 1 0.758889 0.700076 0.708284 11.00000 0.05277 0.05057 = 0.10234 -0.00793 -0.00585 0.00639 AFIX 43 H4 2 0.815211 0.762383 0.703176 11.00000 -1.20000 AFIX 0 C16 1 0.256880 0.662148 0.714247 11.00000 0.05651 0.06900 = 0.06863 0.00807 -0.00575 -0.00900 AFIX 43 H16 2 0.328697 0.683481 0.721729 11.00000 -1.20000 AFIX 0 C14 1 0.341792 -0.011924 0.381858 11.00000 0.07191 0.05878 = 0.05090 -0.00717 -0.00100 0.00839 AFIX 23 H14A 2 0.352315 -0.117092 0.378663 11.00000 -1.20000 H14B 2 0.285989 0.017120 0.348537 11.00000 -1.20000 AFIX 0 C17 1 0.190213 0.721627 0.753600 11.00000 0.08617 0.06599 = 0.05913 -0.00306 -0.00563 -0.01089 AFIX 43 H17 2 0.216959 0.783368 0.787185 11.00000 -1.20000 AFIX 0 C3 1 0.718021 0.692193 0.766461 11.00000 0.06861 0.06699 = 0.08081 -0.02400 -0.01146 0.01390 AFIX 43 H3 2 0.746427 0.750669 0.800809 11.00000 -1.20000 AFIX 0 C28 1 -0.074600 -0.017299 0.354533 11.00000 0.09481 0.06301 = 0.05937 -0.00402 0.00330 0.00782 AFIX 23 H28A 2 -0.097132 0.010935 0.310118 11.00000 -1.20000 H28B 2 -0.071160 -0.123669 0.356635 11.00000 -1.20000 AFIX 0 HKLF 4 REM NRVS1_0m_a.res in P2(1)/c REM wR2 = 0.1191, GooF = S = 1.069, Restrained GooF = 1.069 for all data REM R1 = 0.0415 for 2928 Fo > 4sig(Fo) and 0.0715 for all 4170 data REM 343 parameters refined using 0 restraints END WGHT 0.0603 0.0000 REM Highest difference peak 0.255, deepest hole -0.287, 1-sigma level 0.041 Q1 1 0.1987 0.3618 0.5506 11.00000 0.05 0.26 Q2 1 0.7927 0.7066 0.7018 11.00000 0.05 0.19 Q3 1 0.3635 0.4684 0.6449 11.00000 0.05 0.18 Q4 1 0.4986 0.2948 0.5235 11.00000 0.05 0.17 Q5 1 0.6637 0.5163 0.6618 11.00000 0.05 0.16 Q6 1 0.4989 0.4160 0.6031 11.00000 0.05 0.15 Q7 1 -0.0429 0.1577 0.4304 11.00000 0.05 0.14 Q8 1 0.4279 0.1616 0.4474 11.00000 0.05 0.14 Q9 1 0.1620 0.7240 0.7526 11.00000 0.05 0.14 Q10 1 0.5703 0.3443 0.6232 11.00000 0.05 0.14 Q11 1 0.5908 0.2164 0.4341 11.00000 0.05 0.14 Q12 1 0.5006 0.3038 0.5711 11.00000 0.05 0.14 Q13 1 0.2832 0.0063 0.4496 11.00000 0.05 0.13 Q14 1 -0.1363 -0.1538 0.2837 11.00000 0.05 0.13 Q15 1 0.3784 0.1428 0.4879 11.00000 0.05 0.13 Q16 1 0.3838 -0.2386 0.3430 11.00000 0.05 0.13 Q17 1 -0.0027 0.2933 0.5121 11.00000 0.05 0.13 Q18 1 0.1000 0.3417 0.5403 11.00000 0.05 0.13 Q19 1 0.1796 0.5555 0.6522 11.00000 0.05 0.13 Q20 1 0.3311 0.0041 0.4072 11.00000 0.05 0.12 ; _shelx_res_checksum 24433 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 S2 S -0.06976(5) 0.39289(7) 0.59331(3) 0.0520(2) Uani 1 1 d . . . . . S1 S 0.65130(5) 0.42043(7) 0.53822(3) 0.0518(2) Uani 1 1 d . . . . . O1 O 0.43682(14) 0.0636(2) 0.37335(8) 0.0638(5) Uani 1 1 d . . . . . O2 O 0.31302(14) 0.0243(2) 0.44420(8) 0.0659(5) Uani 1 1 d . . . . . O3 O 0.02740(17) 0.0440(2) 0.37524(9) 0.0767(6) Uani 1 1 d . . . . . N2 N 0.50204(14) 0.3473(2) 0.60636(9) 0.0466(5) Uani 1 1 d . . . . . N4 N 0.11787(15) 0.3763(2) 0.55835(9) 0.0505(5) Uani 1 1 d . . . . . N1 N 0.50805(18) 0.4216(3) 0.73428(10) 0.0703(7) Uani 1 1 d . . . . . H1A H 0.485199 0.419449 0.771565 0.084 Uiso 1 1 calc R U . . . H1B H 0.479157 0.366976 0.703433 0.084 Uiso 1 1 calc R U . . . N3 N 0.28874(16) 0.5161(2) 0.62284(11) 0.0688(6) Uani 1 1 d . . . . . H3A H 0.354644 0.539094 0.629227 0.083 Uiso 1 1 calc R U . . . H3B H 0.266020 0.459260 0.591237 0.083 Uiso 1 1 calc R U . . . O4 O -0.14780(16) 0.0355(2) 0.39548(10) 0.0782(6) Uani 1 1 d . . . . . C1 C 0.58976(19) 0.5112(3) 0.72410(11) 0.0530(6) Uani 1 1 d . . . . . C20 C 0.11050(18) 0.5364(2) 0.65289(11) 0.0468(6) Uani 1 1 d . . . . . C13 C 0.39509(18) 0.1818(3) 0.53138(11) 0.0490(6) Uani 1 1 d . . . . . H13 H 0.344690 0.164457 0.559441 0.059 Uiso 1 1 calc R U . . . C8 C 0.48141(17) 0.2743(2) 0.54765(10) 0.0439(5) Uani 1 1 d . . . . . C12 C 0.38932(18) 0.1186(3) 0.47172(11) 0.0473(6) Uani 1 1 d . . . . . C15 C 0.22034(18) 0.5697(3) 0.66278(12) 0.0511(6) Uani 1 1 d . . . . . C6 C 0.63018(18) 0.5185(2) 0.66370(11) 0.0473(6) Uani 1 1 d . . . . . C7 C 0.58724(18) 0.4280(2) 0.60856(11) 0.0446(5) Uani 1 1 d . . . . . C9 C 0.55554(17) 0.3000(2) 0.50408(11) 0.0443(5) Uani 1 1 d . . . . . C21 C 0.06573(18) 0.4379(2) 0.60113(11) 0.0458(6) Uani 1 1 d . . . . . C27 C -0.1285(2) 0.2000(3) 0.48925(12) 0.0556(6) Uani 1 1 d . . . . . H27 H -0.198848 0.196169 0.497134 0.067 Uiso 1 1 calc R U . . . C19 C 0.0449(2) 0.5989(3) 0.69426(12) 0.0584(7) Uani 1 1 d . . . . . H19 H -0.027066 0.577810 0.688046 0.070 Uiso 1 1 calc R U . . . C11 C 0.46346(19) 0.1430(2) 0.42925(10) 0.0488(6) Uani 1 1 d . . . . . C10 C 0.54779(19) 0.2327(3) 0.44297(11) 0.0509(6) Uani 1 1 d . . . . . H10 H 0.597049 0.248740 0.414034 0.061 Uiso 1 1 calc R U . . . C22 C -0.05250(18) 0.2837(2) 0.52726(11) 0.0476(6) Uani 1 1 d . . . . . C5 C 0.71481(19) 0.6137(3) 0.65742(13) 0.0576(7) Uani 1 1 d . . . . . H5 H 0.742153 0.619040 0.617945 0.069 Uiso 1 1 calc R U . . . C18 C 0.0827(2) 0.6914(3) 0.74429(13) 0.0676(7) Uani 1 1 d . . . . . H18 H 0.037149 0.732463 0.771161 0.081 Uiso 1 1 calc R U . . . C23 C 0.05360(19) 0.2892(2) 0.51600(11) 0.0488(6) Uani 1 1 d . . . . . C24 C 0.0889(2) 0.2088(3) 0.46450(12) 0.0572(7) Uani 1 1 d . . . . . H24 H 0.159048 0.210020 0.456162 0.069 Uiso 1 1 calc R U . . . C2 C 0.6365(2) 0.5999(3) 0.77442(13) 0.0679(8) Uani 1 1 d . . . . . H2 H 0.611109 0.595586 0.814509 0.082 Uiso 1 1 calc R U . . . C25 C 0.0138(2) 0.1300(3) 0.42809(12) 0.0561(6) Uani 1 1 d . . . . . C26 C -0.0920(2) 0.1254(3) 0.44025(12) 0.0552(6) Uani 1 1 d . . . . . C4 C 0.7589(2) 0.7001(3) 0.70828(16) 0.0697(8) Uani 1 1 d . . . . . H4 H 0.815211 0.762383 0.703176 0.084 Uiso 1 1 calc R U . . . C16 C 0.2569(2) 0.6621(3) 0.71425(13) 0.0657(7) Uani 1 1 d . . . . . H16 H 0.328697 0.683481 0.721729 0.079 Uiso 1 1 calc R U . . . C14 C 0.3418(2) -0.0119(3) 0.38186(12) 0.0612(7) Uani 1 1 d . . . . . H14A H 0.352315 -0.117092 0.378663 0.073 Uiso 1 1 calc R U . . . H14B H 0.285989 0.017120 0.348537 0.073 Uiso 1 1 calc R U . . . C17 C 0.1902(2) 0.7216(3) 0.75360(14) 0.0715(8) Uani 1 1 d . . . . . H17 H 0.216959 0.783368 0.787185 0.086 Uiso 1 1 calc R U . . . C3 C 0.7180(2) 0.6922(3) 0.76646(15) 0.0737(9) Uani 1 1 d . . . . . H3 H 0.746427 0.750669 0.800809 0.088 Uiso 1 1 calc R U . . . C28 C -0.0746(2) -0.0173(3) 0.35453(14) 0.0728(8) Uani 1 1 d . . . . . H28A H -0.097132 0.010935 0.310118 0.087 Uiso 1 1 calc R U . . . H28B H -0.071160 -0.123669 0.356635 0.087 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 S2 0.0422(4) 0.0597(4) 0.0554(4) -0.0037(3) 0.0114(3) 0.0007(3) S1 0.0457(4) 0.0611(4) 0.0507(4) 0.0016(3) 0.0142(3) 0.0011(3) O1 0.0697(12) 0.0778(12) 0.0444(10) -0.0100(9) 0.0091(9) 0.0016(10) O2 0.0620(12) 0.0780(12) 0.0581(11) -0.0125(9) 0.0085(9) -0.0083(10) O3 0.0842(15) 0.0841(13) 0.0628(12) -0.0195(10) 0.0130(11) 0.0080(11) N2 0.0419(11) 0.0569(12) 0.0416(11) -0.0003(9) 0.0078(9) 0.0052(9) N4 0.0471(12) 0.0537(12) 0.0518(12) 0.0024(10) 0.0107(10) 0.0019(9) N1 0.0687(15) 0.1009(17) 0.0437(13) -0.0103(12) 0.0171(11) -0.0164(13) N3 0.0430(12) 0.0856(16) 0.0788(16) -0.0004(13) 0.0118(11) -0.0049(11) O4 0.0771(14) 0.0806(13) 0.0742(13) -0.0249(11) -0.0019(11) -0.0017(11) C1 0.0494(15) 0.0602(15) 0.0486(15) -0.0030(12) 0.0020(12) 0.0146(12) C20 0.0479(14) 0.0467(13) 0.0458(13) 0.0086(11) 0.0059(11) 0.0002(11) C13 0.0443(14) 0.0604(15) 0.0435(14) 0.0032(11) 0.0097(11) 0.0009(11) C8 0.0426(13) 0.0517(13) 0.0379(13) 0.0048(10) 0.0070(10) 0.0087(11) C12 0.0436(13) 0.0517(14) 0.0456(14) 0.0029(11) 0.0014(11) 0.0035(11) C15 0.0452(14) 0.0513(14) 0.0563(15) 0.0152(12) 0.0040(12) 0.0003(11) C6 0.0425(13) 0.0458(13) 0.0530(14) 0.0013(11) 0.0028(11) 0.0102(11) C7 0.0418(13) 0.0471(13) 0.0452(13) 0.0065(10) 0.0062(10) 0.0129(11) C9 0.0413(13) 0.0500(13) 0.0425(13) 0.0058(10) 0.0092(10) 0.0086(10) C21 0.0444(13) 0.0450(13) 0.0488(14) 0.0092(11) 0.0095(11) 0.0040(10) C27 0.0517(15) 0.0553(15) 0.0593(16) 0.0001(13) 0.0041(13) 0.0030(12) C19 0.0566(16) 0.0624(16) 0.0574(16) -0.0028(13) 0.0112(13) -0.0052(13) C11 0.0575(15) 0.0542(14) 0.0345(13) 0.0014(11) 0.0047(11) 0.0114(12) C10 0.0522(15) 0.0624(15) 0.0400(13) 0.0066(11) 0.0134(11) 0.0074(12) C22 0.0470(14) 0.0470(13) 0.0496(14) 0.0072(11) 0.0081(11) 0.0055(11) C5 0.0509(15) 0.0524(15) 0.0686(18) 0.0012(13) 0.0041(13) 0.0087(12) C18 0.076(2) 0.0682(18) 0.0601(17) -0.0088(14) 0.0125(15) -0.0039(15) C23 0.0507(14) 0.0487(14) 0.0479(14) 0.0069(11) 0.0096(11) 0.0028(11) C24 0.0531(15) 0.0640(16) 0.0563(16) 0.0024(13) 0.0137(13) 0.0099(13) C2 0.0672(19) 0.0786(19) 0.0563(17) -0.0158(14) 0.0000(14) 0.0147(16) C25 0.0704(18) 0.0515(14) 0.0472(15) -0.0009(12) 0.0095(13) 0.0095(13) C26 0.0618(17) 0.0512(14) 0.0506(15) 0.0018(12) -0.0016(13) 0.0039(12) C4 0.0528(17) 0.0506(16) 0.102(2) -0.0079(16) -0.0059(16) 0.0064(13) C16 0.0565(17) 0.0690(18) 0.0686(18) 0.0081(15) -0.0057(14) -0.0090(14) C14 0.0719(19) 0.0588(16) 0.0509(15) -0.0072(12) -0.0010(13) 0.0084(14) C17 0.086(2) 0.0660(18) 0.0591(17) -0.0031(14) -0.0056(16) -0.0109(16) C3 0.069(2) 0.0670(18) 0.081(2) -0.0240(16) -0.0115(17) 0.0139(15) C28 0.095(2) 0.0630(17) 0.0594(17) -0.0040(14) 0.0033(17) 0.0078(16) 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' S S 0.1246 0.1234 '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 C22 S2 C21 89.64(11) . . ? C9 S1 C7 89.65(11) . . ? C11 O1 C14 106.16(18) . . ? C12 O2 C14 106.28(19) . . ? C25 O3 C28 105.5(2) . . ? C7 N2 C8 111.79(19) . . ? C21 N4 C23 111.9(2) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C15 N3 H3A 120.0 . . ? C15 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C26 O4 C28 106.5(2) . . ? N1 C1 C2 119.8(2) . . ? N1 C1 C6 122.1(2) . . ? C2 C1 C6 118.1(2) . . ? C19 C20 C15 118.4(2) . . ? C19 C20 C21 119.7(2) . . ? C15 C20 C21 121.9(2) . . ? C12 C13 C8 115.7(2) . . ? C12 C13 H13 122.2 . . ? C8 C13 H13 122.2 . . ? N2 C8 C13 124.4(2) . . ? N2 C8 C9 114.6(2) . . ? C13 C8 C9 121.0(2) . . ? C13 C12 O2 127.3(2) . . ? C13 C12 C11 123.1(2) . . ? O2 C12 C11 109.7(2) . . ? N3 C15 C16 120.2(2) . . ? N3 C15 C20 121.5(2) . . ? C16 C15 C20 118.2(2) . . ? C5 C6 C1 118.4(2) . . ? C5 C6 C7 119.7(2) . . ? C1 C6 C7 121.9(2) . . ? N2 C7 C6 125.2(2) . . ? N2 C7 S1 114.35(17) . . ? C6 C7 S1 120.48(18) . . ? C8 C9 C10 122.1(2) . . ? C8 C9 S1 109.61(17) . . ? C10 C9 S1 128.33(18) . . ? N4 C21 C20 125.6(2) . . ? N4 C21 S2 114.16(18) . . ? C20 C21 S2 120.22(17) . . ? C26 C27 C22 115.0(2) . . ? C26 C27 H27 122.5 . . ? C22 C27 H27 122.5 . . ? C18 C19 C20 122.3(3) . . ? C18 C19 H19 118.9 . . ? C20 C19 H19 118.9 . . ? C10 C11 O1 127.3(2) . . ? C10 C11 C12 123.1(2) . . ? O1 C11 C12 109.6(2) . . ? C11 C10 C9 115.1(2) . . ? C11 C10 H10 122.4 . . ? C9 C10 H10 122.4 . . ? C23 C22 C27 122.8(2) . . ? C23 C22 S2 109.07(18) . . ? C27 C22 S2 128.12(19) . . ? C4 C5 C6 121.9(3) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C19 C18 C17 118.6(3) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? N4 C23 C22 115.2(2) . . ? N4 C23 C24 124.3(2) . . ? C22 C23 C24 120.4(2) . . ? C25 C24 C23 115.7(2) . . ? C25 C24 H24 122.2 . . ? C23 C24 H24 122.2 . . ? C3 C2 C1 122.0(3) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C24 C25 O3 127.0(2) . . ? C24 C25 C26 123.1(2) . . ? O3 C25 C26 109.9(2) . . ? C27 C26 O4 127.9(2) . . ? C27 C26 C25 123.0(2) . . ? O4 C26 C25 109.1(2) . . ? C3 C4 C5 118.9(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C17 C16 C15 121.7(3) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? O1 C14 O2 108.29(19) . . ? O1 C14 H14A 110.0 . . ? O2 C14 H14A 110.0 . . ? O1 C14 H14B 110.0 . . ? O2 C14 H14B 110.0 . . ? H14A C14 H14B 108.4 . . ? C16 C17 C18 120.8(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C2 C3 C4 120.8(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? O4 C28 O3 108.9(2) . . ? O4 C28 H28A 109.9 . . ? O3 C28 H28A 109.9 . . ? O4 C28 H28B 109.9 . . ? O3 C28 H28B 109.9 . . ? H28A C28 H28B 108.3 . . ? 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 S2 C22 1.731(2) . ? S2 C21 1.762(2) . ? S1 C9 1.729(2) . ? S1 C7 1.758(2) . ? O1 C11 1.378(3) . ? O1 C14 1.420(3) . ? O2 C12 1.371(3) . ? O2 C14 1.427(3) . ? O3 C25 1.377(3) . ? O3 C28 1.433(3) . ? N2 C7 1.307(3) . ? N2 C8 1.389(3) . ? N4 C21 1.298(3) . ? N4 C23 1.381(3) . ? N1 C1 1.358(3) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N3 C15 1.362(3) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? O4 C26 1.374(3) . ? O4 C28 1.418(3) . ? C1 C2 1.399(4) . ? C1 C6 1.414(3) . ? C20 C19 1.389(3) . ? C20 C15 1.422(3) . ? C20 C21 1.465(3) . ? C13 C12 1.363(3) . ? C13 C8 1.394(3) . ? C13 H13 0.9300 . ? C8 C9 1.402(3) . ? C12 C11 1.384(3) . ? C15 C16 1.399(4) . ? C6 C5 1.401(3) . ? C6 C7 1.465(3) . ? C9 C10 1.405(3) . ? C27 C26 1.352(3) . ? C27 C22 1.401(3) . ? C27 H27 0.9300 . ? C19 C18 1.381(3) . ? C19 H19 0.9300 . ? C11 C10 1.353(3) . ? C10 H10 0.9300 . ? C22 C23 1.398(3) . ? C5 C4 1.384(4) . ? C5 H5 0.9300 . ? C18 C17 1.387(4) . ? C18 H18 0.9300 . ? C23 C24 1.413(3) . ? C24 C25 1.354(3) . ? C24 H24 0.9300 . ? C2 C3 1.360(4) . ? C2 H2 0.9300 . ? C25 C26 1.400(4) . ? C4 C3 1.374(4) . ? C4 H4 0.9300 . ? C16 C17 1.359(4) . ? C16 H16 0.9300 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C17 H17 0.9300 . ? C3 H3 0.9300 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ?