#------------------------------------------------------------------------------ #$Date: 2021-07-17 08:01:51 +0300 (Sat, 17 Jul 2021) $ #$Revision: 267612 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158172.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_7158172 loop_ _publ_author_name 'Gillaizeau, Isabelle' 'Habert, Loic' 'Diachenko, Iryna' 'Retailleau, Pascal' _publ_section_title ; Electrophile Promoted Cyclization of ortho-Aryl Substituted Ynamides: Construction of 3-Amino-4-Halo- or 4-Seleno-Isocoumarin Derivatives ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01075A _journal_year 2021 _chemical_formula_moiety 'C19 H15 F I N O4 S' _chemical_formula_sum 'C19 H15 F I N O4 S' _chemical_formula_weight 499.28 _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/1 _audit_update_record ; 2021-05-06 deposited with the CCDC. 2021-07-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.829(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.4116(4) _cell_length_b 18.7873(10) _cell_length_c 12.5260(6) _cell_measurement_reflns_used 6642 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.0510 _cell_measurement_theta_min 3.9540 _cell_volume 1956.04(17) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_structure_refinement 'SHELXL-2018/1 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2015)' _diffrn_ambient_environment air _diffrn_ambient_temperature 293(2) _diffrn_detector 'Dectris HPAD Pilatus3R 200K' _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.919 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa single' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_unetI/netI 0.0446 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.919 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 24947 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.919 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.056 _diffrn_reflns_theta_min 3.646 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Mo) mm003 X-ray Source' _exptl_absorpt_coefficient_mu 1.777 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.24081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.695 _exptl_crystal_description cube _exptl_crystal_F_000 984 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _refine_diff_density_max 1.057 _refine_diff_density_min -0.714 _refine_diff_density_rms 0.073 _refine_ls_extinction_coef 0.0031(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/1 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 274 _refine_ls_number_reflns 5262 _refine_ls_number_restraints 33 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0354 _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^)+(0.0321P)^2^+1.0040P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0850 _refine_ls_wR_factor_ref 0.0910 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3919 _reflns_number_total 5266 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01075a2.cif _cod_data_source_block LOH-948 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7158172 _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 exp_1_a.res in P2(1)/n exp_1.res created by SHELXL-2018/1 at 16:01:05 on 27-Jun-2018 REM Old TITL exp_1 in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.155, Rweak 0.009, Alpha 0.046, Orientation as input REM Formula found by SHELXT: C16 F I N3 O5 S CELL 0.71073 8.4116 18.7873 12.526 90 98.829 90 ZERR 4 0.0004 0.001 0.0006 0 0.005 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C F I N O S H UNIT 76 4 4 4 16 4 60 L.S. 24 0 0 PLAN 20 BOND $H list 4 fmap 2 53 CONF EQIV $1 -x+1/2, y-1/2, -z+1/2 HTAB C24 F12_$1 EQIV $2 -x+1, -y, -z+1 HTAB C24 O15_$2 HTAB C24B O15_$2 ACTA OMIT 1 2 1 OMIT 1 3 0 OMIT -1 3 1 OMIT -3 5 4 REM REM REM REM ##### WGHT 0.032100 1.004000 EXTI 0.003089 FVAR 0.35128 0.83252 C1 1 0.437836 0.234166 0.444012 11.00000 0.04062 0.04374 = 0.04501 -0.00337 0.01118 0.00146 O2 5 0.366802 0.269528 0.521786 11.00000 0.06036 0.04345 = 0.04417 -0.00015 0.02383 0.00114 C3 1 0.336788 0.341142 0.516339 11.00000 0.05039 0.04623 = 0.04541 -0.00518 0.01844 -0.00272 C4 1 0.383253 0.379027 0.424227 11.00000 0.03983 0.04461 = 0.04076 -0.00164 0.01023 -0.00206 C5 1 0.454372 0.343011 0.345312 11.00000 0.03590 0.04810 = 0.03763 -0.00085 0.00708 -0.00218 C6 1 0.480992 0.267052 0.358809 11.00000 0.03876 0.04903 = 0.03929 -0.00654 0.01087 0.00082 C7 1 0.355327 0.451419 0.416824 11.00000 0.05702 0.04724 = 0.05808 -0.00138 0.01654 0.00435 AFIX 43 H7 7 0.308571 0.474991 0.469449 11.00000 -1.20000 AFIX 0 C8 1 0.397310 0.487803 0.331245 11.00000 0.06597 0.04570 = 0.06583 0.00922 0.00892 0.00111 C9 1 0.466639 0.454962 0.251972 11.00000 0.06841 0.06407 = 0.05503 0.01688 0.01494 -0.00387 AFIX 43 H9 7 0.494972 0.481086 0.194696 11.00000 -1.20000 AFIX 0 N1 4 0.456085 0.161399 0.467292 11.00000 0.04657 0.03998 = 0.05283 -0.00048 0.00795 -0.00169 C10 1 0.493626 0.382416 0.258715 11.00000 0.05769 0.06249 = 0.04329 0.00422 0.01471 -0.00257 AFIX 43 H10 7 0.538644 0.359546 0.204674 11.00000 -1.20000 AFIX 0 O11 5 0.274320 0.367321 0.586944 11.00000 0.09089 0.05382 = 0.06236 -0.00636 0.04388 0.00068 F12 2 0.369479 0.558991 0.324710 11.00000 0.12521 0.05037 = 0.09987 0.02178 0.03072 0.01380 I13 3 0.593794 0.209626 0.248782 11.00000 0.05807 0.06398 = 0.05022 -0.01192 0.02029 0.00604 S14 6 0.609726 0.135215 0.555964 11.00000 0.04390 0.04649 = 0.05870 0.00344 0.01297 0.00484 O15 5 0.651816 0.065608 0.523309 11.00000 0.06308 0.05445 = 0.08285 0.00114 0.02152 0.01915 O16 5 0.722246 0.192343 0.563758 11.00000 0.04696 0.06741 = 0.06970 0.01056 0.00910 -0.00765 C17 1 0.538820 0.126808 0.680597 11.00000 0.04455 0.04792 = 0.05130 0.00569 0.00722 0.00511 C18 1 0.478009 0.062336 0.709824 11.00000 0.06199 0.04482 = 0.06902 0.00365 0.01234 0.00014 AFIX 43 H18 7 0.476310 0.022876 0.664834 11.00000 -1.20000 AFIX 0 C19 1 0.419711 0.057672 0.807352 11.00000 0.06178 0.05933 = 0.07158 0.01561 0.01119 -0.00931 AFIX 43 H19 7 0.378269 0.014631 0.827344 11.00000 -1.20000 AFIX 0 C20 1 0.421970 0.115776 0.875514 11.00000 0.04794 0.07553 = 0.05471 0.00879 0.00164 -0.00188 C21 1 0.483662 0.178819 0.844007 11.00000 0.05904 0.06055 = 0.05450 -0.00463 0.00288 0.00077 AFIX 43 H21 7 0.486354 0.218200 0.889234 11.00000 -1.20000 AFIX 0 C22 1 0.541491 0.185337 0.747583 11.00000 0.05701 0.04496 = 0.05968 0.00406 0.00443 -0.00159 AFIX 43 H22 7 0.581908 0.228624 0.727712 11.00000 -1.20000 AFIX 0 C23 1 0.357168 0.110092 0.981370 11.00000 0.07940 0.11381 = 0.06153 0.01072 0.01700 -0.00838 AFIX 137 H23A 7 0.352119 0.156644 1.012275 11.00000 -1.50000 H23B 7 0.426935 0.080355 1.030288 11.00000 -1.50000 H23C 7 0.251329 0.089671 0.968720 11.00000 -1.50000 AFIX 0 REM ##### REM ##### RIGU N1 C24 > C26B SADI N1 C24 N1 C24B SADI C24 C25 C24B C25B SADI C25 C26 C25B C26B PART 1 C24 1 0.322802 0.112496 0.423321 21.00000 0.05038 0.04329 = 0.06038 -0.00853 0.00971 -0.00014 AFIX 23 H24A 7 0.296218 0.119354 0.345882 21.00000 -1.20000 H24B 7 0.357460 0.063590 0.436227 21.00000 -1.20000 AFIX 0 C25 1 0.177810 0.125823 0.474799 21.00000 0.05645 0.06269 = 0.06874 -0.00304 0.01565 -0.00483 AFIX 43 H25 7 0.188128 0.128891 0.549649 21.00000 -1.20000 AFIX 0 C26 1 0.032631 0.133480 0.415159 21.00000 0.04828 0.07031 = 0.14269 -0.00775 0.02337 0.00909 AFIX 93 H26A 7 0.021323 0.130483 0.340265 21.00000 -1.20000 H26B 7 -0.056977 0.141799 0.448597 21.00000 -1.20000 AFIX 0 PART 2 REM SAME C24 > C26 C24B 1 0.318229 0.111029 0.471799 -21.00000 0.07251 0.03830 = 0.10517 0.00699 -0.04249 -0.02074 AFIX 23 H24C 7 0.350585 0.065506 0.445573 -21.00000 -1.20000 H24D 7 0.310580 0.104479 0.547656 -21.00000 -1.20000 AFIX 0 C25B 1 0.155988 0.124241 0.417261 -21.00000 0.07734 0.04172 = 0.17714 -0.02094 -0.05782 -0.01011 AFIX 43 H25B 7 0.116835 0.152626 0.358227 -21.00000 -1.20000 AFIX 0 C26B 1 0.079394 0.081014 0.481566 -21.00000 0.08442 0.10261 = 0.14604 -0.04938 -0.01289 -0.00999 AFIX 93 H26C 7 0.138913 0.056048 0.538202 -21.00000 -1.20000 H26D 7 -0.032039 0.076681 0.468515 -21.00000 -1.20000 PART 2 AFIX 0 HKLF 4 REM exp_1_a.res in P2(1)/n REM R1 = 0.0354 for 3919 Fo > 4sig(Fo) and 0.0524 for all 5262 data REM 274 parameters refined using 33 restraints END WGHT 0.0321 1.0040 REM Highest difference peak 1.057, deepest hole -0.714, 1-sigma level 0.073 Q1 1 0.5205 0.1811 0.2629 11.00000 0.05 1.06 Q2 1 0.6862 0.2580 0.2230 11.00000 0.05 0.36 Q3 1 0.2191 0.1275 0.3969 11.00000 0.05 0.31 Q4 1 0.6225 0.2037 0.2323 11.00000 0.05 0.28 Q5 1 0.4493 0.2002 0.4512 11.00000 0.05 0.27 Q6 1 0.5706 0.1328 0.6261 11.00000 0.05 0.26 Q7 1 0.6697 0.1791 0.2398 11.00000 0.05 0.26 Q8 1 0.4995 0.2417 0.2698 11.00000 0.05 0.25 Q9 1 0.5042 0.2565 0.4213 11.00000 0.05 0.25 Q10 1 0.5861 0.1366 0.9347 11.00000 0.05 0.25 Q11 1 0.3990 0.3624 0.3746 11.00000 0.05 0.24 Q12 1 0.2430 0.2161 0.8705 11.00000 0.05 0.24 Q13 1 0.4971 0.2985 0.3565 11.00000 0.05 0.23 Q14 1 0.3748 0.4437 0.1615 11.00000 0.05 0.23 Q15 1 0.4591 0.3611 0.4061 11.00000 0.05 0.22 Q16 1 0.5931 0.3615 0.2397 11.00000 0.05 0.22 Q17 1 0.2181 0.3380 0.5607 11.00000 0.05 0.22 Q18 1 0.6895 0.3768 0.2005 11.00000 0.05 0.21 Q19 1 0.4175 0.2483 0.3827 11.00000 0.05 0.21 Q20 1 0.4696 0.2847 0.7539 11.00000 0.05 0.21 ; _shelx_res_checksum 63125 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 0.4378(3) 0.23417(15) 0.4440(2) 0.0426(6) Uani 1 1 d . . . . . O2 O 0.3668(2) 0.26953(10) 0.52179(15) 0.0477(4) Uani 1 1 d . . . . . C3 C 0.3368(3) 0.34114(15) 0.5163(2) 0.0462(6) Uani 1 1 d . . . . . C4 C 0.3833(3) 0.37903(14) 0.4242(2) 0.0413(5) Uani 1 1 d . . . . . C5 C 0.4544(3) 0.34301(14) 0.3453(2) 0.0404(5) Uani 1 1 d . . . . . C6 C 0.4810(3) 0.26705(15) 0.3588(2) 0.0419(5) Uani 1 1 d . . . . . C7 C 0.3553(4) 0.45142(16) 0.4168(3) 0.0533(7) Uani 1 1 d . . . . . H7 H 0.308571 0.474991 0.469449 0.064 Uiso 1 1 calc R U . . . C8 C 0.3973(4) 0.48780(17) 0.3312(3) 0.0593(8) Uani 1 1 d . . . . . C9 C 0.4666(4) 0.45496(18) 0.2520(3) 0.0619(8) Uani 1 1 d . . . . . H9 H 0.494972 0.481086 0.194696 0.074 Uiso 1 1 calc R U . . . N1 N 0.4561(3) 0.16140(12) 0.46729(19) 0.0464(5) Uani 1 1 d D . . . . C10 C 0.4936(4) 0.38242(17) 0.2587(2) 0.0538(7) Uani 1 1 d . . . . . H10 H 0.538644 0.359546 0.204674 0.065 Uiso 1 1 calc R U . . . O11 O 0.2743(3) 0.36732(12) 0.58694(19) 0.0657(6) Uani 1 1 d . . . . . F12 F 0.3695(3) 0.55899(11) 0.3247(2) 0.0904(7) Uani 1 1 d . . . . . I13 I 0.59379(2) 0.20963(2) 0.24878(2) 0.05617(10) Uani 1 1 d . . . . . S14 S 0.60973(8) 0.13521(4) 0.55596(6) 0.04916(17) Uani 1 1 d . . . . . O15 O 0.6518(3) 0.06561(12) 0.5233(2) 0.0657(6) Uani 1 1 d . . . . . O16 O 0.7222(3) 0.19234(12) 0.5638(2) 0.0613(6) Uani 1 1 d . . . . . C17 C 0.5388(3) 0.12681(15) 0.6806(2) 0.0479(6) Uani 1 1 d . . . . . C18 C 0.4780(4) 0.06234(17) 0.7098(3) 0.0584(7) Uani 1 1 d . . . . . H18 H 0.476310 0.022876 0.664834 0.070 Uiso 1 1 calc R U . . . C19 C 0.4197(4) 0.05767(19) 0.8074(3) 0.0641(8) Uani 1 1 d . . . . . H19 H 0.378269 0.014631 0.827344 0.077 Uiso 1 1 calc R U . . . C20 C 0.4220(4) 0.11578(19) 0.8755(3) 0.0600(8) Uani 1 1 d . . . . . C21 C 0.4837(4) 0.17882(19) 0.8440(3) 0.0586(7) Uani 1 1 d . . . . . H21 H 0.486354 0.218200 0.889234 0.070 Uiso 1 1 calc R U . . . C22 C 0.5415(4) 0.18534(17) 0.7476(3) 0.0544(7) Uani 1 1 d . . . . . H22 H 0.581908 0.228624 0.727712 0.065 Uiso 1 1 calc R U . . . C23 C 0.3572(5) 0.1101(3) 0.9814(3) 0.0843(12) Uani 1 1 d . . . . . H23A H 0.352119 0.156644 1.012275 0.126 Uiso 1 1 calc R U . . . H23B H 0.426935 0.080355 1.030288 0.126 Uiso 1 1 calc R U . . . H23C H 0.251329 0.089671 0.968720 0.126 Uiso 1 1 calc R U . . . C24 C 0.3228(5) 0.1125(3) 0.4233(4) 0.0512(12) Uani 0.833(8) 1 d D . P A 1 H24A H 0.296218 0.119354 0.345882 0.061 Uiso 0.833(8) 1 calc R U P A 1 H24B H 0.357460 0.063590 0.436227 0.061 Uiso 0.833(8) 1 calc R U P A 1 C25 C 0.1778(6) 0.1258(3) 0.4748(4) 0.0620(13) Uani 0.833(8) 1 d D . P A 1 H25 H 0.188128 0.128891 0.549649 0.074 Uiso 0.833(8) 1 calc R U P A 1 C26 C 0.0326(5) 0.1335(3) 0.4152(6) 0.0862(18) Uani 0.833(8) 1 d D . P A 1 H26A H 0.021323 0.130483 0.340265 0.103 Uiso 0.833(8) 1 calc R U P A 1 H26B H -0.056977 0.141799 0.448597 0.103 Uiso 0.833(8) 1 calc R U P A 1 C24B C 0.318(3) 0.1110(14) 0.472(3) 0.078(10) Uani 0.167(8) 1 d D . P A 2 H24C H 0.350585 0.065506 0.445573 0.093 Uiso 0.167(8) 1 calc R U P A 2 H24D H 0.310580 0.104479 0.547656 0.093 Uiso 0.167(8) 1 calc R U P A 2 C25B C 0.156(3) 0.1242(15) 0.417(3) 0.107(11) Uani 0.167(8) 1 d D . P A 2 H25B H 0.116835 0.152626 0.358227 0.128 Uiso 0.167(8) 1 calc R U P A 2 C26B C 0.079(4) 0.0810(17) 0.482(3) 0.114(11) Uani 0.167(8) 1 d D . P A 2 H26C H 0.138913 0.056048 0.538202 0.137 Uiso 0.167(8) 1 calc R U P A 2 H26D H -0.032039 0.076681 0.468515 0.137 Uiso 0.167(8) 1 calc R U P A 2 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 0.0406(13) 0.0437(14) 0.0450(14) -0.0034(11) 0.0112(10) 0.0015(11) O2 0.0604(12) 0.0434(10) 0.0442(10) -0.0002(8) 0.0238(9) 0.0011(8) C3 0.0504(15) 0.0462(15) 0.0454(14) -0.0052(11) 0.0184(11) -0.0027(12) C4 0.0398(12) 0.0446(14) 0.0408(13) -0.0016(10) 0.0102(10) -0.0021(11) C5 0.0359(12) 0.0481(14) 0.0376(12) -0.0008(10) 0.0071(9) -0.0022(10) C6 0.0388(12) 0.0490(14) 0.0393(12) -0.0065(11) 0.0109(10) 0.0008(11) C7 0.0570(17) 0.0472(16) 0.0581(17) -0.0014(13) 0.0165(13) 0.0044(13) C8 0.0660(19) 0.0457(16) 0.0658(19) 0.0092(14) 0.0089(15) 0.0011(14) C9 0.0684(19) 0.064(2) 0.0550(17) 0.0169(15) 0.0149(15) -0.0039(16) N1 0.0466(12) 0.0400(12) 0.0528(13) -0.0005(10) 0.0079(10) -0.0017(10) C10 0.0577(17) 0.0625(19) 0.0433(14) 0.0042(13) 0.0147(12) -0.0026(14) O11 0.0909(16) 0.0538(13) 0.0624(13) -0.0064(10) 0.0439(12) 0.0007(11) F12 0.1252(19) 0.0504(11) 0.0999(17) 0.0218(11) 0.0307(14) 0.0138(12) I13 0.05807(14) 0.06398(16) 0.05022(13) -0.01192(8) 0.02029(9) 0.00604(9) S14 0.0439(3) 0.0465(4) 0.0587(4) 0.0034(3) 0.0130(3) 0.0048(3) O15 0.0631(13) 0.0544(13) 0.0828(16) 0.0011(11) 0.0215(11) 0.0192(10) O16 0.0470(11) 0.0674(14) 0.0697(14) 0.0106(11) 0.0091(10) -0.0076(10) C17 0.0446(14) 0.0479(15) 0.0513(15) 0.0057(12) 0.0072(11) 0.0051(12) C18 0.0620(18) 0.0448(16) 0.0690(19) 0.0037(14) 0.0123(15) 0.0001(14) C19 0.0618(19) 0.0593(19) 0.072(2) 0.0156(16) 0.0112(16) -0.0093(15) C20 0.0479(16) 0.076(2) 0.0547(17) 0.0088(16) 0.0016(13) -0.0019(15) C21 0.0590(18) 0.0606(19) 0.0545(18) -0.0046(14) 0.0029(14) 0.0008(15) C22 0.0570(16) 0.0450(15) 0.0597(18) 0.0041(13) 0.0044(13) -0.0016(13) C23 0.079(3) 0.114(3) 0.062(2) 0.011(2) 0.0170(19) -0.008(2) C24 0.050(2) 0.043(2) 0.060(3) -0.009(2) 0.0097(19) -0.0001(16) C25 0.056(3) 0.063(3) 0.069(3) -0.003(2) 0.016(2) -0.005(2) C26 0.048(2) 0.070(3) 0.143(5) -0.008(3) 0.023(3) 0.009(2) C24B 0.073(11) 0.038(11) 0.11(3) 0.007(14) -0.042(13) -0.021(9) C25B 0.077(12) 0.042(12) 0.18(3) -0.021(16) -0.058(14) -0.010(10) C26B 0.084(14) 0.10(2) 0.15(3) -0.049(16) -0.013(15) -0.010(15) 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' H H 0.0000 0.0000 '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 C6 C1 O2 122.7(2) . . ? C6 C1 N1 125.8(2) . . ? O2 C1 N1 111.5(2) . . ? C3 O2 C1 122.1(2) . . ? O11 C3 O2 117.6(2) . . ? O11 C3 C4 125.7(3) . . ? O2 C3 C4 116.7(2) . . ? C7 C4 C5 120.9(3) . . ? C7 C4 C3 118.0(2) . . ? C5 C4 C3 121.1(2) . . ? C10 C5 C4 118.0(3) . . ? C10 C5 C6 124.2(2) . . ? C4 C5 C6 117.8(2) . . ? C1 C6 C5 119.6(2) . . ? C1 C6 I13 119.8(2) . . ? C5 C6 I13 120.58(18) . . ? C8 C7 C4 119.0(3) . . ? C8 C7 H7 120.5 . . ? C4 C7 H7 120.5 . . ? F12 C8 C7 118.6(3) . . ? F12 C8 C9 119.2(3) . . ? C7 C8 C9 122.3(3) . . ? C8 C9 C10 118.9(3) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C1 N1 C24 118.2(3) . . ? C1 N1 C24B 124.1(11) . . ? C1 N1 S14 118.81(18) . . ? C24 N1 S14 122.3(3) . . ? C24B N1 S14 108.5(10) . . ? C9 C10 C5 121.0(3) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? O16 S14 O15 121.15(15) . . ? O16 S14 N1 105.42(13) . . ? O15 S14 N1 106.47(13) . . ? O16 S14 C17 108.58(15) . . ? O15 S14 C17 107.68(14) . . ? N1 S14 C17 106.70(13) . . ? C22 C17 C18 120.5(3) . . ? C22 C17 S14 119.4(2) . . ? C18 C17 S14 120.1(2) . . ? C17 C18 C19 118.9(3) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 121.3(3) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C21 C20 C19 118.2(3) . . ? C21 C20 C23 121.0(3) . . ? C19 C20 C23 120.8(3) . . ? C20 C21 C22 121.9(3) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C21 C22 C17 119.2(3) . . ? C21 C22 H22 120.4 . . ? C17 C22 H22 120.4 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 N1 110.9(4) . . ? C25 C24 H24A 109.5 . . ? N1 C24 H24A 109.5 . . ? C25 C24 H24B 109.5 . . ? N1 C24 H24B 109.5 . . ? H24A C24 H24B 108.0 . . ? C26 C25 C24 121.0(5) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 H26A 120.0 . . ? C25 C26 H26B 120.0 . . ? H26A C26 H26B 120.0 . . ? C25B C24B N1 123(2) . . ? C25B C24B H24C 106.5 . . ? N1 C24B H24C 106.5 . . ? C25B C24B H24D 106.5 . . ? N1 C24B H24D 106.5 . . ? H24C C24B H24D 106.5 . . ? C26B C25B C24B 97(2) . . ? C26B C25B H25B 131.7 . . ? C24B C25B H25B 131.7 . . ? C25B C26B H26C 120.0 . . ? C25B C26B H26D 120.0 . . ? H26C C26B H26D 120.0 . . ? 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 C1 C6 1.331(4) . ? C1 O2 1.388(3) . ? C1 N1 1.401(4) . ? O2 C3 1.369(3) . ? C3 O11 1.201(3) . ? C3 C4 1.459(4) . ? C4 C7 1.381(4) . ? C4 C5 1.405(4) . ? C5 C10 1.394(4) . ? C5 C6 1.450(4) . ? C6 I13 2.089(3) . ? C7 C8 1.363(4) . ? C7 H7 0.9300 . ? C8 F12 1.358(4) . ? C8 C9 1.373(5) . ? C9 C10 1.382(5) . ? C9 H9 0.9300 . ? N1 C24 1.488(5) . ? N1 C24B 1.504(16) . ? N1 S14 1.645(2) . ? C10 H10 0.9300 . ? S14 O16 1.424(2) . ? S14 O15 1.431(2) . ? S14 C17 1.762(3) . ? C17 C22 1.381(4) . ? C17 C18 1.386(4) . ? C18 C19 1.387(5) . ? C18 H18 0.9300 . ? C19 C20 1.384(5) . ? C19 H19 0.9300 . ? C20 C21 1.375(5) . ? C20 C23 1.513(5) . ? C21 C22 1.375(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.486(6) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.338(7) . ? C25 H25 0.9300 . ? C26 H26A 0.9300 . ? C26 H26B 0.9300 . ? C24B C25B 1.451(18) . ? C24B H24C 0.9700 . ? C24B H24D 0.9700 . ? C25B C26B 1.37(2) . ? C25B H25B 0.9300 . ? C26B H26C 0.9300 . ? C26B H26D 0.9300 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C24^a H24A^a F12 0.97 2.62 3.426(5) 140.3 2_545 yes C24^a H24B^a O15 0.97 2.48 3.412(6) 160.4 3_656 yes C24B^b H24C^b O15 0.97 2.49 3.33(3) 143.9 3_656 yes 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 C6 C1 O2 C3 -0.3(4) . . . . ? N1 C1 O2 C3 180.0(2) . . . . ? C1 O2 C3 O11 179.7(3) . . . . ? C1 O2 C3 C4 0.0(4) . . . . ? O11 C3 C4 C7 0.7(5) . . . . ? O2 C3 C4 C7 -179.6(2) . . . . ? O11 C3 C4 C5 -179.3(3) . . . . ? O2 C3 C4 C5 0.3(4) . . . . ? C7 C4 C5 C10 -0.9(4) . . . . ? C3 C4 C5 C10 179.1(3) . . . . ? C7 C4 C5 C6 179.6(2) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? O2 C1 C6 C5 0.2(4) . . . . ? N1 C1 C6 C5 180.0(2) . . . . ? O2 C1 C6 I13 178.07(18) . . . . ? N1 C1 C6 I13 -2.2(4) . . . . ? C10 C5 C6 C1 -179.4(3) . . . . ? C4 C5 C6 C1 0.1(4) . . . . ? C10 C5 C6 I13 2.8(3) . . . . ? C4 C5 C6 I13 -177.71(18) . . . . ? C5 C4 C7 C8 0.2(4) . . . . ? C3 C4 C7 C8 -179.8(3) . . . . ? C4 C7 C8 F12 -180.0(3) . . . . ? C4 C7 C8 C9 0.0(5) . . . . ? F12 C8 C9 C10 -179.6(3) . . . . ? C7 C8 C9 C10 0.5(5) . . . . ? C6 C1 N1 C24 -89.7(4) . . . . ? O2 C1 N1 C24 90.1(3) . . . . ? C6 C1 N1 C24B -116.6(18) . . . . ? O2 C1 N1 C24B 63.1(18) . . . . ? C6 C1 N1 S14 99.4(3) . . . . ? O2 C1 N1 S14 -80.9(3) . . . . ? C8 C9 C10 C5 -1.2(5) . . . . ? C4 C5 C10 C9 1.4(4) . . . . ? C6 C5 C10 C9 -179.1(3) . . . . ? C1 N1 S14 O16 -19.0(2) . . . . ? C24 N1 S14 O16 170.4(3) . . . . ? C24B N1 S14 O16 -168.2(17) . . . . ? C1 N1 S14 O15 -148.9(2) . . . . ? C24 N1 S14 O15 40.5(3) . . . . ? C24B N1 S14 O15 61.9(17) . . . . ? C1 N1 S14 C17 96.3(2) . . . . ? C24 N1 S14 C17 -74.3(3) . . . . ? C24B N1 S14 C17 -52.9(17) . . . . ? O16 S14 C17 C22 25.3(3) . . . . ? O15 S14 C17 C22 158.2(2) . . . . ? N1 S14 C17 C22 -87.9(2) . . . . ? O16 S14 C17 C18 -156.0(2) . . . . ? O15 S14 C17 C18 -23.1(3) . . . . ? N1 S14 C17 C18 90.8(3) . . . . ? C22 C17 C18 C19 0.1(4) . . . . ? S14 C17 C18 C19 -178.6(2) . . . . ? C17 C18 C19 C20 -0.3(5) . . . . ? C18 C19 C20 C21 0.1(5) . . . . ? C18 C19 C20 C23 179.7(3) . . . . ? C19 C20 C21 C22 0.3(5) . . . . ? C23 C20 C21 C22 -179.3(3) . . . . ? C20 C21 C22 C17 -0.5(5) . . . . ? C18 C17 C22 C21 0.3(4) . . . . ? S14 C17 C22 C21 179.0(2) . . . . ? C1 N1 C24 C25 -67.6(5) . . . . ? S14 N1 C24 C25 103.1(4) . . . . ? N1 C24 C25 C26 131.2(5) . . . . ? C1 N1 C24B C25B 23(5) . . . . ? S14 N1 C24B C25B 170(3) . . . . ? N1 C24B C25B C26B -157(3) . . . . ?