#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:02:50 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304785 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064319.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_7064319 loop_ _publ_author_name 'Moskalik, Mikhail Yu.' 'Garagan, Ivan A.' 'Myasnikova, Valentina S.' 'Borodina, Tatyana N.' 'Shainyan, Bagrat A.' _publ_section_title ; Skeletal rearrangements and structures of halosulfonamidation products of caryophyllene ; _journal_issue 4 _journal_name_full 'New Journal of Chemistry' _journal_page_first 1935 _journal_page_last 1942 _journal_paper_doi 10.1039/D5NJ03976B _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C18 H28 F3 I N2 O2 S' _chemical_formula_sum 'C18 H28 F3 I N2 O2 S' _chemical_formula_weight 520.38 _chemical_melting_point 462.6 _chemical_name_systematic N-(9-iodo-4,4,8-trimethyltricyclo[6.3.1.0^2,5]dodecan-1-yl)-N'-((trifluoromethyl)sulfonyl)acetimidamide _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2025-02-28 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2025-03-13 deposited with the CCDC. 2025-12-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.2852(9) _cell_length_b 16.239(2) _cell_length_c 18.497(3) _cell_measurement_reflns_used 9828 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.34 _cell_measurement_theta_min 2.51 _cell_volume 2188.3(5) _computing_cell_refinement 'SAINT V8.32B (BRUKER, 2016)' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'SAINT V8.32B (BRUKER, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'Bruker D8 VENTURE PHOTON 100 CMOS' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1107 _diffrn_reflns_av_unetI/netI 0.0755 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 41380 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.747 _diffrn_reflns_theta_min 2.202 _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.599 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.3920 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1721 before and 0.0821 after correction. The Ratio of minimum to maximum transmission is 0.5258. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.580 _exptl_crystal_description needle _exptl_crystal_F_000 1048 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ethanol' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.445 _exptl_crystal_size_min 0.285 _refine_diff_density_max 0.416 _refine_diff_density_min -0.748 _refine_diff_density_rms 0.138 _refine_ls_abs_structure_details ; Flack x determined using 1209 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.011(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 248 _refine_ls_number_reflns 5080 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.991 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0321 _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^)+(0.0402P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.0801 _reflns_Friedel_coverage 0.754 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.984 _reflns_number_gt 3483 _reflns_number_total 5080 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj03976b2.cif _cod_data_source_block 5b _cod_original_cell_volume 2188.2(5) _cod_database_code 7064319 _shelxl_version_number 2013-3 _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_estimated_absorpt_t_max 0.659 _shelx_estimated_absorpt_t_min 0.447 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C2(H2), C5(H5), C9(H9) 2.b Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C10(H10A,H10B), C11(H11A,H11B), C7(H7A,H7B), C6(H6A,H6B), C3(H3A,H3B) 2.c Aromatic/amide H refined with riding coordinates: N1(H1) 2.d Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B, H17C) ; _shelx_res_file ; TITL a in P2(1)2(1)2(1) CELL 0.71073 7.2852 16.2387 18.4965 90 90 90 ZERR 4 0.0009 0.002 0.0025 0 0 0 LATT -1 SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5-X,-Y,0.5+Z SFAC C H N O F S I UNIT 72 112 8 8 12 4 4 L.S. 10 PLAN 7 SIZE 0.285 0.445 0.6 TEMP -273.15 CONF BOND $H HTAB fmap 2 acta MORE -1 REM REM REM WGHT 0.040200 FVAR 0.45755 I1 7 0.463785 -0.166208 0.320571 11.00000 0.09324 0.05563 = 0.11038 -0.00167 -0.04615 0.02124 S1 6 -0.250955 0.173419 0.385947 11.00000 0.02785 0.03737 = 0.03630 -0.00229 0.00495 -0.00101 F1 5 -0.331973 0.019946 0.411211 11.00000 0.12995 0.04928 = 0.08605 0.00883 0.02107 -0.02540 F2 5 -0.158905 0.074304 0.488787 11.00000 0.14394 0.15372 = 0.08010 0.06570 -0.04326 -0.02189 F3 5 -0.439519 0.104708 0.487420 11.00000 0.14816 0.10215 = 0.10533 0.00731 0.08677 -0.02208 O1 4 -0.406998 0.176138 0.339697 11.00000 0.02620 0.06775 = 0.06803 0.00662 -0.00410 0.00278 O2 4 -0.222558 0.242463 0.432071 11.00000 0.05339 0.05258 = 0.06721 -0.02346 0.01742 -0.00338 N2 3 -0.083965 0.139364 0.342590 11.00000 0.02309 0.04029 = 0.03505 -0.00990 -0.00087 -0.00343 N1 3 0.214226 0.125027 0.310682 11.00000 0.02115 0.03407 = 0.04154 -0.00914 -0.00443 -0.00283 AFIX 43 H1 2 0.327285 0.143400 0.315200 11.00000 -1.20000 AFIX 0 C18 1 -0.297864 0.088164 0.446758 11.00000 0.07934 0.05982 = 0.04859 0.01045 0.01135 -0.00872 C16 1 0.089148 0.162643 0.349366 11.00000 0.02849 0.03217 = 0.02915 -0.00868 -0.00095 0.00156 C1 1 0.187564 0.054667 0.259840 11.00000 0.02692 0.02867 = 0.03592 -0.00906 -0.00252 0.00138 C2 1 0.082619 0.081597 0.191866 11.00000 0.02950 0.03160 = 0.03446 -0.00446 -0.00060 -0.00372 AFIX 13 H2 2 0.007808 0.033413 0.175581 11.00000 -1.20000 AFIX 0 C5 1 0.195618 0.110763 0.126383 11.00000 0.04542 0.04842 = 0.03628 -0.00529 0.00376 -0.00533 AFIX 13 H5 2 0.289583 0.150559 0.144619 11.00000 -1.20000 AFIX 0 C4 1 0.026282 0.161427 0.102147 11.00000 0.05748 0.04353 = 0.03928 0.00618 -0.00431 -0.00648 C14 1 -0.104055 0.114982 0.052578 11.00000 0.07240 0.06456 = 0.04802 0.00775 -0.01370 -0.01040 AFIX 137 H14A 2 -0.227082 0.139059 0.056090 11.00000 -1.50000 H14B 2 -0.108753 0.056981 0.067098 11.00000 -1.50000 H14C 2 -0.060351 0.118965 0.002591 11.00000 -1.50000 AFIX 0 C12 1 0.383651 0.029118 0.238413 11.00000 0.03108 0.03834 = 0.04529 -0.01468 0.00070 0.00326 AFIX 23 H12A 2 0.442532 0.075724 0.212864 11.00000 -1.20000 H12B 2 0.455001 0.018639 0.283027 11.00000 -1.20000 AFIX 0 C8 1 0.394658 -0.047293 0.190192 11.00000 0.03941 0.04889 = 0.05792 -0.02386 -0.00524 0.00957 C9 1 0.301767 -0.118738 0.229309 11.00000 0.05740 0.03640 = 0.06521 -0.01598 -0.01931 0.01187 AFIX 13 H9 2 0.288700 -0.164642 0.193639 11.00000 -1.20000 AFIX 0 C10 1 0.111550 -0.098374 0.256610 11.00000 0.04878 0.03281 = 0.05844 -0.00094 -0.00780 -0.00029 AFIX 23 H10A 2 0.068884 -0.144082 0.287789 11.00000 -1.20000 H10B 2 0.027316 -0.095116 0.214707 11.00000 -1.20000 AFIX 0 C11 1 0.097814 -0.017874 0.299394 11.00000 0.04189 0.03443 = 0.03915 -0.00299 -0.00352 0.00006 AFIX 23 H11A 2 0.158011 -0.025208 0.346946 11.00000 -1.20000 H11B 2 -0.033148 -0.005036 0.308171 11.00000 -1.20000 AFIX 0 C7 1 0.294475 -0.038664 0.115658 11.00000 0.06429 0.05817 = 0.04960 -0.02729 -0.00023 0.01204 AFIX 23 H7A 2 0.351077 -0.078056 0.081427 11.00000 -1.20000 H7B 2 0.164939 -0.055489 0.122254 11.00000 -1.20000 AFIX 0 C6 1 0.296414 0.046173 0.080886 11.00000 0.07387 0.07799 = 0.04049 -0.01193 0.01325 -0.00156 AFIX 23 H6A 2 0.238014 0.042792 0.032649 11.00000 -1.20000 H6B 2 0.425241 0.063879 0.073923 11.00000 -1.20000 AFIX 0 C3 1 -0.036764 0.159192 0.181727 11.00000 0.04052 0.04037 = 0.04377 0.00297 -0.00326 0.00323 AFIX 23 H3A 2 -0.169935 0.149317 0.187925 11.00000 -1.20000 H3B 2 0.004302 0.207114 0.210590 11.00000 -1.20000 AFIX 0 C13 1 0.067187 0.246128 0.070148 11.00000 0.09282 0.05730 = 0.06435 0.02150 -0.00230 -0.01271 AFIX 137 H13A 2 0.121535 0.239586 0.022023 11.00000 -1.50000 H13B 2 0.153365 0.275503 0.101612 11.00000 -1.50000 H13C 2 -0.047082 0.277663 0.066269 11.00000 -1.50000 AFIX 0 C15 1 0.599662 -0.062242 0.173479 11.00000 0.04905 0.07189 = 0.10398 -0.03632 0.00541 0.02365 AFIX 137 H15A 2 0.669760 -0.062336 0.218700 11.00000 -1.50000 H15B 2 0.645324 -0.018348 0.141876 11.00000 -1.50000 H15C 2 0.613993 -0.115528 0.149255 11.00000 -1.50000 AFIX 0 C17 1 0.158210 0.231573 0.396481 11.00000 0.03421 0.05638 = 0.06247 -0.03165 -0.00206 -0.00646 AFIX 137 H17A 2 0.288823 0.240880 0.386789 11.00000 -1.50000 H17B 2 0.141637 0.216782 0.447432 11.00000 -1.50000 H17C 2 0.089138 0.281937 0.385899 11.00000 -1.50000 AFIX 0 HKLF 4 REM a in P2(1)2(1)2(1) REM R1 = 0.0321 for 3483 Fo > 4sig(Fo) and 0.0692 for all 5080 data REM 248 parameters refined using 0 restraints END WGHT 0.0402 0.0000 REM Instructions for potential hydrogen bonds EQIV $1 x+1, y, z HTAB N1 O1_$1 HTAB C12 I1 EQIV $2 -x, y-1/2, -z+1/2 HTAB C9 S1_$2 HTAB C11 N2 HTAB C17 O1_$1 EQIV $3 x+1/2, -y+1/2, -z+1 HTAB C17 O2_$3 REM Highest difference peak 0.416, deepest hole -0.748, 1-sigma level 0.138 Q1 1 -0.1475 0.1601 0.5143 11.00000 0.05 0.42 Q2 1 -0.2244 0.0213 0.4477 11.00000 0.05 0.38 Q3 1 0.1090 0.1686 0.4847 11.00000 0.05 0.37 Q4 1 -0.1913 0.1996 0.4618 11.00000 0.05 0.37 Q5 1 0.0952 0.0185 -0.0055 11.00000 0.05 0.36 Q6 1 0.3101 0.2585 0.0024 11.00000 0.05 0.35 Q7 1 0.2402 0.1933 0.4984 11.00000 0.05 0.35 ; _shelx_res_checksum 67692 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, 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 I1 I 0.46379(6) -0.16621(2) 0.32057(2) 0.08642(19) Uani 1 1 d . . . . . S1 S -0.25096(14) 0.17342(5) 0.38595(5) 0.0338(2) Uani 1 1 d . . . . . F1 F -0.3320(6) 0.01995(16) 0.41121(18) 0.0884(12) Uani 1 1 d . . . . . F2 F -0.1589(8) 0.0743(3) 0.4888(2) 0.1259(17) Uani 1 1 d . . . . . F3 F -0.4395(7) 0.1047(2) 0.4874(2) 0.1185(17) Uani 1 1 d . . . . . O1 O -0.4070(4) 0.17614(18) 0.33970(17) 0.0540(8) Uani 1 1 d . . . . . O2 O -0.2226(5) 0.24246(16) 0.43207(18) 0.0577(9) Uani 1 1 d . . . . . N2 N -0.0840(5) 0.13936(17) 0.34259(17) 0.0328(7) Uani 1 1 d . . . . . N1 N 0.2142(4) 0.12503(17) 0.31068(17) 0.0323(7) Uani 1 1 d . . . . . H1 H 0.3273 0.1434 0.3152 0.039 Uiso 1 1 calc R U . . . C18 C -0.2979(9) 0.0882(3) 0.4468(3) 0.0626(15) Uani 1 1 d . . . . . C16 C 0.0891(5) 0.1626(2) 0.34937(19) 0.0299(8) Uani 1 1 d . . . . . C1 C 0.1876(6) 0.05467(19) 0.2598(2) 0.0305(8) Uani 1 1 d . . . . . C2 C 0.0826(6) 0.08160(19) 0.1919(2) 0.0319(8) Uani 1 1 d . . . . . H2 H 0.0078 0.0334 0.1756 0.038 Uiso 1 1 calc R U . . . C5 C 0.1956(7) 0.1108(2) 0.1264(2) 0.0434(10) Uani 1 1 d . . . . . H5 H 0.2896 0.1506 0.1446 0.052 Uiso 1 1 calc R U . . . C4 C 0.0263(7) 0.1614(2) 0.1021(2) 0.0468(10) Uani 1 1 d . . . . . C14 C -0.1041(9) 0.1150(3) 0.0526(3) 0.0617(15) Uani 1 1 d . . . . . H14A H -0.2271 0.1391 0.0561 0.092 Uiso 1 1 calc R U . . . H14B H -0.1088 0.0570 0.0671 0.092 Uiso 1 1 calc R U . . . H14C H -0.0604 0.1190 0.0026 0.092 Uiso 1 1 calc R U . . . C12 C 0.3837(6) 0.0291(2) 0.2384(2) 0.0382(10) Uani 1 1 d . . . . . H12A H 0.4425 0.0757 0.2129 0.046 Uiso 1 1 calc R U . . . H12B H 0.4550 0.0186 0.2830 0.046 Uiso 1 1 calc R U . . . C8 C 0.3947(7) -0.0473(2) 0.1902(3) 0.0487(11) Uani 1 1 d . . . . . C9 C 0.3018(7) -0.1187(2) 0.2293(3) 0.0530(13) Uani 1 1 d . . . . . H9 H 0.2887 -0.1646 0.1936 0.064 Uiso 1 1 calc R U . . . C10 C 0.1116(7) -0.0984(2) 0.2566(2) 0.0467(11) Uani 1 1 d . . . . . H10A H 0.0689 -0.1441 0.2878 0.056 Uiso 1 1 calc R U . . . H10B H 0.0273 -0.0951 0.2147 0.056 Uiso 1 1 calc R U . . . C11 C 0.0978(6) -0.0179(2) 0.2994(2) 0.0385(10) Uani 1 1 d . . . . . H11A H 0.1580 -0.0252 0.3469 0.046 Uiso 1 1 calc R U . . . H11B H -0.0331 -0.0050 0.3082 0.046 Uiso 1 1 calc R U . . . C7 C 0.2945(8) -0.0387(3) 0.1157(2) 0.0574(14) Uani 1 1 d . . . . . H7A H 0.3511 -0.0781 0.0814 0.069 Uiso 1 1 calc R U . . . H7B H 0.1649 -0.0555 0.1223 0.069 Uiso 1 1 calc R U . . . C6 C 0.2964(9) 0.0462(3) 0.0809(3) 0.0641(15) Uani 1 1 d . . . . . H6A H 0.2380 0.0428 0.0326 0.077 Uiso 1 1 calc R U . . . H6B H 0.4252 0.0639 0.0739 0.077 Uiso 1 1 calc R U . . . C3 C -0.0368(6) 0.1592(2) 0.1817(2) 0.0416(9) Uani 1 1 d . . . . . H3A H -0.1699 0.1493 0.1879 0.050 Uiso 1 1 calc R U . . . H3B H 0.0043 0.2071 0.2106 0.050 Uiso 1 1 calc R U . . . C13 C 0.0672(10) 0.2461(3) 0.0701(3) 0.0715(17) Uani 1 1 d . . . . . H13A H 0.1215 0.2396 0.0220 0.107 Uiso 1 1 calc R U . . . H13B H 0.1534 0.2755 0.1016 0.107 Uiso 1 1 calc R U . . . H13C H -0.0471 0.2777 0.0663 0.107 Uiso 1 1 calc R U . . . C15 C 0.5997(8) -0.0622(3) 0.1735(4) 0.0750(17) Uani 1 1 d . . . . . H15A H 0.6698 -0.0623 0.2187 0.112 Uiso 1 1 calc R U . . . H15B H 0.6453 -0.0183 0.1419 0.112 Uiso 1 1 calc R U . . . H15C H 0.6140 -0.1155 0.1493 0.112 Uiso 1 1 calc R U . . . C17 C 0.1582(7) 0.2316(2) 0.3965(3) 0.0510(12) Uani 1 1 d . . . . . H17A H 0.2888 0.2409 0.3868 0.077 Uiso 1 1 calc R U . . . H17B H 0.1416 0.2168 0.4474 0.077 Uiso 1 1 calc R U . . . H17C H 0.0891 0.2819 0.3859 0.077 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 I1 0.0932(3) 0.05563(18) 0.1104(3) -0.00167(18) -0.0462(3) 0.02124(19) S1 0.0279(5) 0.0374(4) 0.0363(5) -0.0023(4) 0.0049(4) -0.0010(4) F1 0.130(4) 0.0493(14) 0.086(2) 0.0088(14) 0.021(2) -0.0254(18) F2 0.144(4) 0.154(3) 0.080(2) 0.066(2) -0.043(3) -0.022(3) F3 0.148(4) 0.102(2) 0.105(3) 0.007(2) 0.087(3) -0.022(3) O1 0.0262(17) 0.0678(18) 0.068(2) 0.0066(16) -0.0041(15) 0.0028(14) O2 0.053(2) 0.0526(16) 0.067(2) -0.0235(15) 0.0174(18) -0.0034(15) N2 0.0231(19) 0.0403(15) 0.0350(17) -0.0099(12) -0.0009(15) -0.0034(13) N1 0.0212(18) 0.0341(13) 0.0415(18) -0.0091(13) -0.0044(16) -0.0028(13) C18 0.079(5) 0.060(3) 0.049(3) 0.010(2) 0.011(3) -0.009(3) C16 0.028(2) 0.0322(15) 0.0292(18) -0.0087(15) -0.0010(16) 0.0016(17) C1 0.027(2) 0.0287(15) 0.036(2) -0.0091(14) -0.0025(18) 0.0014(15) C2 0.030(2) 0.0316(15) 0.034(2) -0.0045(14) -0.0006(18) -0.0037(15) C5 0.045(3) 0.048(2) 0.036(2) -0.0053(17) 0.004(2) -0.005(2) C4 0.057(3) 0.0435(18) 0.039(2) 0.0062(17) -0.004(2) -0.006(2) C14 0.072(4) 0.065(3) 0.048(3) 0.008(2) -0.014(3) -0.010(3) C12 0.031(2) 0.0383(17) 0.045(2) -0.0147(16) 0.001(2) 0.0033(17) C8 0.039(3) 0.049(2) 0.058(3) -0.024(2) -0.005(2) 0.0096(19) C9 0.057(3) 0.0364(19) 0.065(3) -0.016(2) -0.019(3) 0.012(2) C10 0.049(3) 0.0328(17) 0.058(3) -0.0009(17) -0.008(2) -0.0003(18) C11 0.042(3) 0.0344(16) 0.039(2) -0.0030(15) -0.004(2) 0.0001(17) C7 0.064(4) 0.058(2) 0.050(3) -0.027(2) 0.000(3) 0.012(2) C6 0.074(4) 0.078(3) 0.040(3) -0.012(2) 0.013(3) -0.002(3) C3 0.041(2) 0.0404(17) 0.044(2) 0.0030(16) -0.003(2) 0.0032(18) C13 0.093(5) 0.057(3) 0.064(3) 0.021(2) -0.002(3) -0.013(3) C15 0.049(3) 0.072(3) 0.104(4) -0.036(3) 0.005(3) 0.024(3) C17 0.034(3) 0.056(2) 0.062(3) -0.032(2) -0.002(2) -0.006(2) 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' F F 0.0171 0.0103 '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' I I -0.4742 1.8119 '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 O1 S1 O2 116.9(2) . . ? O1 S1 N2 108.98(18) . . ? O1 S1 C18 104.2(3) . . ? O2 S1 N2 118.31(19) . . ? O2 S1 C18 104.9(2) . . ? N2 S1 C18 101.2(2) . . ? C16 N2 S1 126.5(2) . . ? C16 N1 H1 116.2 . . ? C16 N1 C1 127.6(3) . . ? C1 N1 H1 116.2 . . ? F1 C18 S1 111.6(3) . . ? F2 C18 S1 110.9(4) . . ? F2 C18 F1 107.6(5) . . ? F2 C18 F3 107.9(5) . . ? F3 C18 S1 110.4(4) . . ? F3 C18 F1 108.2(5) . . ? N2 C16 C17 125.9(3) . . ? N1 C16 N2 118.6(3) . . ? N1 C16 C17 115.5(3) . . ? N1 C1 C2 111.3(3) . . ? N1 C1 C12 104.3(3) . . ? N1 C1 C11 110.1(3) . . ? C2 C1 C12 109.2(3) . . ? C11 C1 C2 113.4(3) . . ? C11 C1 C12 108.2(3) . . ? C1 C2 H2 107.2 . . ? C1 C2 C5 117.8(3) . . ? C1 C2 C3 127.8(3) . . ? C5 C2 H2 107.2 . . ? C5 C2 C3 87.4(3) . . ? C3 C2 H2 107.2 . . ? C2 C5 H5 107.4 . . ? C2 C5 C4 88.0(3) . . ? C4 C5 H5 107.4 . . ? C6 C5 C2 118.5(3) . . ? C6 C5 H5 107.4 . . ? C6 C5 C4 125.9(4) . . ? C14 C4 C5 114.1(4) . . ? C14 C4 C3 112.2(4) . . ? C14 C4 C13 109.6(4) . . ? C3 C4 C5 87.0(3) . . ? C13 C4 C5 115.8(4) . . ? C13 C4 C3 116.7(3) . . ? C4 C14 H14A 109.5 . . ? C4 C14 H14B 109.5 . . ? C4 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 C12 H12A 108.6 . . ? C1 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C8 C12 C1 114.7(3) . . ? C8 C12 H12A 108.6 . . ? C8 C12 H12B 108.6 . . ? C12 C8 C7 114.6(4) . . ? C12 C8 C15 107.1(4) . . ? C9 C8 C12 108.5(4) . . ? C9 C8 C7 106.2(4) . . ? C9 C8 C15 113.9(4) . . ? C15 C8 C7 106.8(5) . . ? I1 C9 H9 107.2 . . ? C8 C9 I1 113.1(3) . . ? C8 C9 H9 107.2 . . ? C10 C9 I1 108.2(3) . . ? C10 C9 C8 113.5(3) . . ? C10 C9 H9 107.2 . . ? C9 C10 H10A 108.6 . . ? C9 C10 H10B 108.6 . . ? C9 C10 C11 114.8(4) . . ? H10A C10 H10B 107.5 . . ? C11 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C1 C11 H11A 109.1 . . ? C1 C11 H11B 109.1 . . ? C10 C11 C1 112.4(3) . . ? C10 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? C8 C7 H7A 108.1 . . ? C8 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? C6 C7 C8 116.7(4) . . ? C6 C7 H7A 108.1 . . ? C6 C7 H7B 108.1 . . ? C5 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 C5 112.5(4) . . ? C7 C6 H6A 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C2 C3 H3A 114.0 . . ? C2 C3 H3B 114.0 . . ? C4 C3 C2 88.1(3) . . ? C4 C3 H3A 114.0 . . ? C4 C3 H3B 114.0 . . ? H3A C3 H3B 111.2 . . ? C4 C13 H13A 109.5 . . ? C4 C13 H13B 109.5 . . ? C4 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C9 2.199(5) . ? S1 O1 1.423(3) . ? S1 O2 1.424(3) . ? S1 N2 1.559(3) . ? S1 C18 1.816(5) . ? F1 C18 1.312(6) . ? F2 C18 1.296(7) . ? F3 C18 1.305(7) . ? N2 C16 1.323(5) . ? N1 H1 0.8800 . ? N1 C16 1.310(5) . ? N1 C1 1.492(4) . ? C16 C17 1.505(5) . ? C1 C2 1.535(5) . ? C1 C12 1.539(6) . ? C1 C11 1.533(5) . ? C2 H2 1.0000 . ? C2 C5 1.539(6) . ? C2 C3 1.543(5) . ? C5 H5 1.0000 . ? C5 C4 1.549(6) . ? C5 C6 1.532(7) . ? C4 C14 1.520(6) . ? C4 C3 1.542(6) . ? C4 C13 1.527(5) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C8 1.530(5) . ? C8 C9 1.526(7) . ? C8 C7 1.566(7) . ? C8 C15 1.544(7) . ? C9 H9 1.0000 . ? C9 C10 1.512(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C11 1.531(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C6 1.520(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 I1 C9 C10 C11 77.0(4) . . . . ? S1 N2 C16 N1 177.1(3) . . . . ? S1 N2 C16 C17 -5.0(6) . . . . ? O1 S1 N2 C16 144.1(3) . . . . ? O1 S1 C18 F1 55.0(5) . . . . ? O1 S1 C18 F2 175.0(4) . . . . ? O1 S1 C18 F3 -65.5(5) . . . . ? O2 S1 N2 C16 7.4(4) . . . . ? O2 S1 C18 F1 178.3(4) . . . . ? O2 S1 C18 F2 -61.7(5) . . . . ? O2 S1 C18 F3 57.9(5) . . . . ? N2 S1 C18 F1 -58.1(5) . . . . ? N2 S1 C18 F2 61.8(4) . . . . ? N2 S1 C18 F3 -178.6(4) . . . . ? N1 C1 C2 C5 91.5(4) . . . . ? N1 C1 C2 C3 -18.6(5) . . . . ? N1 C1 C12 C8 175.6(3) . . . . ? N1 C1 C11 C10 -165.3(3) . . . . ? C18 S1 N2 C16 -106.4(4) . . . . ? C16 N1 C1 C2 69.9(5) . . . . ? C16 N1 C1 C12 -172.5(3) . . . . ? C16 N1 C1 C11 -56.7(5) . . . . ? C1 N1 C16 N2 -2.4(6) . . . . ? C1 N1 C16 C17 179.5(3) . . . . ? C1 C2 C5 C4 -154.9(3) . . . . ? C1 C2 C5 C6 74.6(5) . . . . ? C1 C2 C3 C4 146.7(4) . . . . ? C1 C12 C8 C9 -57.7(5) . . . . ? C1 C12 C8 C7 60.8(5) . . . . ? C1 C12 C8 C15 179.0(4) . . . . ? C2 C1 C12 C8 -65.4(4) . . . . ? C2 C1 C11 C10 69.4(4) . . . . ? C2 C5 C4 C14 -90.1(4) . . . . ? C2 C5 C4 C3 22.9(3) . . . . ? C2 C5 C4 C13 141.3(4) . . . . ? C2 C5 C6 C7 -9.6(7) . . . . ? C5 C2 C3 C4 23.0(3) . . . . ? C5 C4 C3 C2 -22.9(3) . . . . ? C4 C5 C6 C7 -119.8(5) . . . . ? C14 C4 C3 C2 92.0(4) . . . . ? C12 C1 C2 C5 -23.1(4) . . . . ? C12 C1 C2 C3 -133.2(4) . . . . ? C12 C1 C11 C10 -51.9(4) . . . . ? C12 C8 C9 I1 -72.7(4) . . . . ? C12 C8 C9 C10 51.1(5) . . . . ? C12 C8 C7 C6 33.9(6) . . . . ? C8 C9 C10 C11 -49.4(5) . . . . ? C8 C7 C6 C5 -63.3(7) . . . . ? C9 C8 C7 C6 153.6(4) . . . . ? C9 C10 C11 C1 49.7(5) . . . . ? C11 C1 C2 C5 -143.8(3) . . . . ? C11 C1 C2 C3 106.1(4) . . . . ? C11 C1 C12 C8 58.4(5) . . . . ? C7 C8 C9 I1 163.7(3) . . . . ? C7 C8 C9 C10 -72.6(4) . . . . ? C6 C5 C4 C14 34.3(6) . . . . ? C6 C5 C4 C3 147.3(4) . . . . ? C6 C5 C4 C13 -94.3(5) . . . . ? C3 C2 C5 C4 -22.9(3) . . . . ? C3 C2 C5 C6 -153.4(4) . . . . ? C13 C4 C3 C2 -140.4(5) . . . . ? C15 C8 C9 I1 46.5(5) . . . . ? C15 C8 C9 C10 170.3(4) . . . . ? C15 C8 C7 C6 -84.6(5) . . . . ?