#------------------------------------------------------------------------------ #$Date: 2019-12-20 03:49:12 +0200 (Fri, 20 Dec 2019) $ #$Revision: 245417 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125672.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_7125672 loop_ _publ_author_name 'Qiu, Yi-Feng' 'Niu, Yue-Jie' 'Song, Xian-Rong' 'Wei, Xi' 'Chen, Hui' 'Li, Shun-Xi' 'Wang, Xi-Cun' 'Huo, Cong-De' 'Quan, Zheng-Jun' 'Liang, Yong-Min' _publ_section_title ; Iodine Promoted Cascade Cycloisomerization of 1-En-6,11-diynes ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC08286G _journal_year 2020 _chemical_formula_moiety 'C29 H23 I N2 O3 S' _chemical_formula_sum 'C29 H23 I N2 O3 S' _chemical_formula_weight 606.45 _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-06-19 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-06-20 deposited with the CCDC. 2019-12-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 25.670(2) _cell_length_b 10.5220(7) _cell_length_c 9.8072(12) _cell_measurement_reflns_used 1456 _cell_measurement_temperature 292.86(10) _cell_measurement_theta_max 26.1560 _cell_measurement_theta_min 3.8720 _cell_volume 2648.9(4) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment air _diffrn_ambient_temperature 292.86(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0733 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 38.00 78.00 1.00 15.00 -- 25.05 178.00 30.00 40 2 \w -2.00 72.00 1.00 15.00 -- 25.05 77.00 60.00 74 3 \w 42.00 88.00 1.00 15.00 -- 25.05 57.00 150.00 46 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0165093000 _diffrn_orient_matrix_UB_12 -0.0411013000 _diffrn_orient_matrix_UB_13 0.0377329000 _diffrn_orient_matrix_UB_21 0.0221487000 _diffrn_orient_matrix_UB_22 0.0282130000 _diffrn_orient_matrix_UB_23 -0.0308448000 _diffrn_orient_matrix_UB_31 0.0011350000 _diffrn_orient_matrix_UB_32 0.0453944000 _diffrn_orient_matrix_UB_33 0.0533618000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_unetI/netI 0.0698 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6329 _diffrn_reflns_point_group_measured_fraction_full 0.798 _diffrn_reflns_point_group_measured_fraction_max 0.790 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.020 _diffrn_reflns_theta_min 3.706 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.321 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.48306 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.521 _exptl_crystal_description block _exptl_crystal_F_000 1216 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.628 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.073 _refine_ls_abs_structure_details ; Flack x determined using 749 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 326 _refine_ls_number_reflns 4113 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0515 _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^)+(0.0271P)^2^+0.9490P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0938 _refine_ls_wR_factor_ref 0.1061 _reflns_Friedel_coverage 0.493 _reflns_Friedel_fraction_full 0.573 _reflns_Friedel_fraction_max 0.556 _reflns_number_gt 3092 _reflns_number_total 4113 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc08286g2.cif _cod_data_source_block lim_0617 _cod_database_code 7125672 _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. ; _reflns_odcompleteness_completeness 99.52 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C8(H8) 2.b Secondary CH2 refined with riding coordinates: C17(H17A,H17B), C38(H38A,H38B), C3AA(H3AA,H3AB) 2.c Aromatic/amide H refined with riding coordinates: C4(H4), C10(H10), C11(H11), C12(H12), C25(H25), C3(H3), C0AA(H0AA), C2AA(H2AA), C6(H6), C5AA(H5AA), C6AA(H6AA), C7AA(H7AA), C8AA(H8AA) 2.d Idealised Me refined as rotating group: C29(H29A,H29B,H29C) ; _shelx_res_file ; TITL lim_0617 in Pna21 #33 lim_0617.res created by SHELXL-2018/3 at 16:43:26 on 19-Jun-2019 REM reset to Pna21 #33 CELL 0.71073 25.669994 10.522024 9.807189 90 90 90 ZERR 4 0.002002 0.000677 0.001178 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-X,0.5+Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SFAC C H I N O S UNIT 116 92 4 8 12 4 L.S. 20 PLAN 20 BOND $h htab conf fmap 2 53 acta SHEL 999 0.81 REM REM REM WGHT 0.027100 0.949000 FVAR 3.32840 I1 3 -0.480656 -0.643667 -0.117380 11.00000 0.05482 0.03798 = 0.09887 0.00569 0.01712 0.01041 S2 6 -0.625109 -0.651085 0.199159 11.00000 0.05165 0.03430 = 0.06169 0.00720 -0.00732 -0.00504 C4 1 -0.560070 0.032202 -0.132846 11.00000 0.05067 0.03056 = 0.05695 0.00057 0.00737 0.00112 AFIX 43 H4 2 -0.570228 0.112297 -0.102827 11.00000 -1.20000 AFIX 0 C5 1 -0.563120 -0.197926 -0.111517 11.00000 0.04115 0.03024 = 0.04548 -0.00856 0.00438 0.00666 O7 5 -0.714484 -0.217057 0.211753 11.00000 0.05531 0.05918 = 0.11884 -0.03330 0.03571 -0.01606 C8 1 -0.566587 -0.440995 -0.088283 11.00000 0.03653 0.02837 = 0.04282 0.00243 -0.00234 0.00554 AFIX 13 H8 2 -0.565543 -0.441944 -0.188167 11.00000 -1.20000 AFIX 0 C9 1 -0.675105 -0.153233 0.214930 11.00000 0.05601 0.03487 = 0.06116 -0.00543 0.01582 -0.00116 C10 1 -0.711246 -0.001963 0.382950 11.00000 0.07055 0.04568 = 0.06594 -0.00550 0.03056 -0.00458 AFIX 43 H10 2 -0.744297 -0.029135 0.357286 11.00000 -1.20000 AFIX 0 C11 1 -0.529433 -0.206163 -0.222621 11.00000 0.05698 0.03597 = 0.05571 -0.00413 0.00636 0.00473 AFIX 43 H11 2 -0.518771 -0.285651 -0.253288 11.00000 -1.20000 AFIX 0 C12 1 -0.753095 -0.805912 0.036043 11.00000 0.06427 0.06470 = 0.06664 -0.00152 -0.00696 -0.01953 AFIX 43 H12 2 -0.760369 -0.856643 -0.039240 11.00000 -1.20000 AFIX 0 C13 1 -0.634184 -0.170659 0.107162 11.00000 0.04478 0.02744 = 0.05501 -0.01307 0.00869 -0.00158 C15 1 -0.667328 -0.053534 0.319712 11.00000 0.04676 0.03012 = 0.05235 -0.00355 0.01217 -0.00398 C16 1 -0.578702 -0.076050 -0.066342 11.00000 0.04949 0.02215 = 0.03901 -0.00649 -0.00893 -0.00083 C17 1 -0.512537 -0.470725 -0.034855 11.00000 0.05231 0.03222 = 0.06442 0.00129 0.01006 0.00107 AFIX 23 H17A 2 -0.513992 -0.477733 0.063693 11.00000 -1.20000 H17B 2 -0.489452 -0.400743 -0.057077 11.00000 -1.20000 AFIX 0 C19 1 -0.583517 -0.309491 -0.041524 11.00000 0.05005 0.02424 = 0.04353 0.00003 0.00170 -0.00337 C23 1 -0.689876 -0.695260 0.169823 11.00000 0.04968 0.03446 = 0.04702 0.00246 0.00583 -0.00403 C25 1 -0.703000 -0.765280 0.056122 11.00000 0.04021 0.04670 = 0.06088 0.00082 0.00278 -0.01027 AFIX 43 H25 2 -0.677506 -0.785187 -0.007780 11.00000 -1.20000 AFIX 0 N27 4 -0.612486 -0.524745 0.105618 11.00000 0.04860 0.02808 = 0.04283 0.00145 0.00268 -0.00883 C29 1 -0.847249 -0.819072 0.098721 11.00000 0.05390 0.14631 = 0.13890 0.03403 -0.01118 -0.03673 AFIX 137 H29A 2 -0.851872 -0.838872 0.003935 11.00000 -1.50000 H29B 2 -0.871163 -0.753194 0.124568 11.00000 -1.50000 H29C 2 -0.853768 -0.893616 0.152520 11.00000 -1.50000 AFIX 0 O35 5 -0.592549 -0.750686 0.146164 11.00000 0.04936 0.04041 = 0.09072 0.00947 -0.00631 0.00418 O37 5 -0.621560 -0.611653 0.337626 11.00000 0.09922 0.05374 = 0.04993 0.00187 -0.01095 -0.02817 C38 1 -0.606303 -0.539433 -0.040443 11.00000 0.05281 0.02813 = 0.05408 -0.00296 -0.00169 0.00010 AFIX 23 H38A 2 -0.639381 -0.526121 -0.086076 11.00000 -1.20000 H38B 2 -0.594124 -0.624451 -0.061568 11.00000 -1.20000 AFIX 0 C40 1 -0.618334 -0.295742 0.064387 11.00000 0.03699 0.03118 = 0.04921 -0.00893 -0.00041 -0.00127 C3 1 -0.619137 -0.014696 0.359849 11.00000 0.06553 0.04389 = 0.05088 -0.00771 0.01033 0.01114 AFIX 43 H3 2 -0.589833 -0.049786 0.318715 11.00000 -1.20000 AFIX 0 C0AA 1 -0.612957 -0.067449 0.045173 11.00000 0.05196 0.02116 = 0.05261 -0.01116 0.00270 0.00307 AFIX 43 H0AA 2 -0.621495 0.012781 0.078088 11.00000 -1.20000 AFIX 0 C2AA 1 -0.780492 -0.700933 0.234721 11.00000 0.04630 0.07364 = 0.10493 0.01170 0.02320 0.00286 AFIX 43 H2AA 2 -0.806848 -0.677270 0.294628 11.00000 -1.20000 AFIX 0 C1AA 1 -0.792639 -0.774731 0.122302 11.00000 0.04192 0.06926 = 0.08036 0.02249 -0.00284 -0.01064 C4AA 1 -0.656372 0.127478 0.519769 11.00000 0.11753 0.04458 = 0.03976 -0.00452 0.01154 0.01327 C6 1 -0.705935 0.088709 0.482892 11.00000 0.08903 0.05651 = 0.06519 -0.00846 0.03031 0.01464 AFIX 43 H6 2 -0.735122 0.123389 0.524983 11.00000 -1.20000 AFIX 0 C5AA 1 -0.612942 0.075608 0.460250 11.00000 0.07673 0.07305 = 0.06526 -0.00907 -0.00440 -0.00133 AFIX 43 H5AA 2 -0.579814 0.101022 0.487270 11.00000 -1.20000 AFIX 0 C3AA 1 -0.641061 -0.409232 0.142293 11.00000 0.04760 0.03198 = 0.04875 -0.00303 0.01369 -0.00532 AFIX 23 H3AA 2 -0.638324 -0.394473 0.239661 11.00000 -1.20000 H3AB 2 -0.677615 -0.419218 0.119637 11.00000 -1.20000 AFIX 0 C6AA 1 -0.729683 -0.661416 0.259974 11.00000 0.09142 0.05027 = 0.06048 -0.00590 0.01902 -0.00821 AFIX 43 H6AA 2 -0.722234 -0.612632 0.336608 11.00000 -1.20000 AFIX 0 C7AA 1 -0.511748 -0.099135 -0.287470 11.00000 0.04707 0.04780 = 0.06114 0.00464 0.01420 0.00193 AFIX 43 H7AA 2 -0.489560 -0.106576 -0.362007 11.00000 -1.20000 AFIX 0 C9AA 1 -0.649739 0.227183 0.625925 11.00000 0.14425 0.09117 = 0.06161 -0.01180 0.00608 0.02517 C8AA 1 -0.527002 0.021544 -0.241785 11.00000 0.06056 0.03711 = 0.05600 0.00675 0.00622 -0.00421 AFIX 43 H8AA 2 -0.514699 0.094093 -0.285338 11.00000 -1.20000 AFIX 0 N0BA 4 -0.644555 0.300711 0.703303 11.00000 0.25954 0.13158 = 0.08932 -0.07426 -0.01207 0.01424 HKLF 4 REM lim_0617 in Pna21 #33 REM wR2 = 0.1061, GooF = S = 1.067, Restrained GooF = 1.067 for all data REM R1 = 0.0515 for 3092 Fo > 4sig(Fo) and 0.0755 for all 4113 data REM 326 parameters refined using 1 restraints END WGHT 0.0271 0.9490 REM Instructions for potential hydrogen bonds HTAB C38 I1 REM Highest difference peak 0.628, deepest hole -0.473, 1-sigma level 0.073 Q1 1 -0.5208 -0.6334 -0.1144 11.00000 0.05 0.46 Q2 1 -0.4782 -0.5852 -0.0416 11.00000 0.05 0.37 Q3 1 -0.4966 -0.6366 -0.2464 11.00000 0.05 0.37 Q4 1 -0.4971 -0.6298 0.0172 11.00000 0.05 0.34 Q5 1 -0.4618 -0.6580 0.0174 11.00000 0.05 0.33 Q6 1 -0.6391 -0.5776 0.2463 11.00000 0.05 0.29 Q7 1 -0.4360 -0.6250 -0.1074 11.00000 0.05 0.28 Q8 1 -0.4883 -0.5913 -0.2066 11.00000 0.05 0.28 Q9 1 -0.6615 -0.6665 0.1950 11.00000 0.05 0.27 Q10 1 -0.5590 -0.0439 -0.1220 11.00000 0.05 0.27 Q11 1 -0.5796 -0.2521 -0.1199 11.00000 0.05 0.26 Q12 1 -0.4786 -0.5044 0.0271 11.00000 0.05 0.25 Q13 1 -0.6964 -0.5610 0.3859 11.00000 0.05 0.25 Q14 1 -0.5187 -0.4939 0.2484 11.00000 0.05 0.25 Q15 1 -0.5188 -0.3488 -0.1170 11.00000 0.05 0.24 Q16 1 -0.4654 -0.3437 -0.3164 11.00000 0.05 0.24 Q17 1 -0.7191 -0.6170 0.3788 11.00000 0.05 0.24 Q18 1 -0.4659 -0.6429 -0.2497 11.00000 0.05 0.23 Q19 1 -0.5224 -0.0365 0.0309 11.00000 0.05 0.23 Q20 1 -0.6399 -0.1229 0.2104 11.00000 0.05 0.23 ; _shelx_res_checksum 32296 _olex2_date_sample_data_collection 2019-06-17 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.901 _oxdiff_exptl_absorpt_empirical_full_min 0.480 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' 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 I1 I -0.48066(2) -0.64367(5) -0.11738(12) 0.0639(2) Uani 1 1 d . S2 S -0.62511(9) -0.6511(2) 0.1992(3) 0.0492(6) Uani 1 1 d . C4 C -0.5601(3) 0.0322(7) -0.1328(14) 0.046(2) Uani 1 1 d . H4 H -0.570228 0.112297 -0.102827 0.055 Uiso 1 1 calc R C5 C -0.5631(3) -0.1979(6) -0.1115(14) 0.0390(19) Uani 1 1 d . O7 O -0.7145(3) -0.2171(7) 0.2118(11) 0.078(3) Uani 1 1 d . C8 C -0.5666(3) -0.4410(7) -0.0883(11) 0.036(2) Uani 1 1 d . H8 H -0.565543 -0.441944 -0.188167 0.043 Uiso 1 1 calc R C9 C -0.6751(4) -0.1532(8) 0.2149(11) 0.051(3) Uani 1 1 d . C10 C -0.7112(4) -0.0020(8) 0.3830(17) 0.061(3) Uani 1 1 d . H10 H -0.744297 -0.029135 0.357286 0.073 Uiso 1 1 calc R C11 C -0.5294(3) -0.2062(9) -0.2226(11) 0.050(3) Uani 1 1 d . H11 H -0.518771 -0.285651 -0.253288 0.059 Uiso 1 1 calc R C12 C -0.7531(4) -0.8059(11) 0.0360(13) 0.065(3) Uani 1 1 d . H12 H -0.760369 -0.856643 -0.039240 0.078 Uiso 1 1 calc R C13 C -0.6342(3) -0.1707(8) 0.1072(11) 0.042(2) Uani 1 1 d . C15 C -0.6673(3) -0.0535(8) 0.3197(10) 0.043(2) Uani 1 1 d . C16 C -0.5787(3) -0.0760(7) -0.0663(9) 0.037(2) Uani 1 1 d . C17 C -0.5125(3) -0.4707(8) -0.0349(11) 0.050(3) Uani 1 1 d . H17A H -0.513992 -0.477733 0.063693 0.060 Uiso 1 1 calc R H17B H -0.489452 -0.400743 -0.057077 0.060 Uiso 1 1 calc R C19 C -0.5835(3) -0.3095(8) -0.0415(10) 0.039(2) Uani 1 1 d . C23 C -0.6899(4) -0.6953(9) 0.1698(10) 0.044(2) Uani 1 1 d . C25 C -0.7030(3) -0.7653(9) 0.0561(12) 0.049(3) Uani 1 1 d . H25 H -0.677506 -0.785187 -0.007780 0.059 Uiso 1 1 calc R N27 N -0.6125(3) -0.5247(6) 0.1056(8) 0.0398(18) Uani 1 1 d . C29 C -0.8472(5) -0.8191(16) 0.0987(19) 0.113(6) Uani 1 1 d . H29A H -0.851872 -0.838872 0.003935 0.170 Uiso 1 1 calc GR H29B H -0.871163 -0.753194 0.124568 0.170 Uiso 1 1 calc GR H29C H -0.853768 -0.893616 0.152520 0.170 Uiso 1 1 calc GR O35 O -0.5925(2) -0.7507(6) 0.1462(8) 0.060(2) Uani 1 1 d . O37 O -0.6216(3) -0.6117(6) 0.3376(7) 0.068(2) Uani 1 1 d . C38 C -0.6063(3) -0.5394(8) -0.0404(10) 0.045(2) Uani 1 1 d . H38A H -0.639381 -0.526121 -0.086076 0.054 Uiso 1 1 calc R H38B H -0.594124 -0.624451 -0.061568 0.054 Uiso 1 1 calc R C40 C -0.6183(3) -0.2957(8) 0.0644(11) 0.039(2) Uani 1 1 d . C3 C -0.6191(4) -0.0147(8) 0.3598(12) 0.053(3) Uani 1 1 d . H3 H -0.589833 -0.049786 0.318715 0.064 Uiso 1 1 calc R C0AA C -0.6130(3) -0.0674(8) 0.0452(10) 0.042(2) Uani 1 1 d . H0AA H -0.621495 0.012781 0.078088 0.050 Uiso 1 1 calc R C2AA C -0.7805(4) -0.7009(12) 0.2347(16) 0.075(4) Uani 1 1 d . H2AA H -0.806848 -0.677270 0.294628 0.090 Uiso 1 1 calc R C1AA C -0.7926(4) -0.7747(12) 0.1223(15) 0.064(3) Uani 1 1 d . C4AA C -0.6564(6) 0.1275(10) 0.5198(12) 0.067(3) Uani 1 1 d . C6 C -0.7059(5) 0.0887(11) 0.4829(13) 0.070(3) Uani 1 1 d . H6 H -0.735122 0.123389 0.524983 0.084 Uiso 1 1 calc R C5AA C -0.6129(5) 0.0756(11) 0.4603(12) 0.072(3) Uani 1 1 d . H5AA H -0.579814 0.101022 0.487270 0.086 Uiso 1 1 calc R C3AA C -0.6411(3) -0.4092(8) 0.1423(11) 0.043(2) Uani 1 1 d . H3AA H -0.638324 -0.394473 0.239661 0.051 Uiso 1 1 calc R H3AB H -0.677615 -0.419218 0.119637 0.051 Uiso 1 1 calc R C6AA C -0.7297(5) -0.6614(10) 0.2600(13) 0.067(3) Uani 1 1 d . H6AA H -0.722234 -0.612632 0.336608 0.081 Uiso 1 1 calc R C7AA C -0.5117(3) -0.0991(9) -0.2875(12) 0.052(3) Uani 1 1 d . H7AA H -0.489560 -0.106576 -0.362007 0.062 Uiso 1 1 calc R C9AA C -0.6497(7) 0.2272(16) 0.6259(16) 0.099(5) Uani 1 1 d . C8AA C -0.5270(4) 0.0215(9) -0.2418(11) 0.051(3) Uani 1 1 d . H8AA H -0.514699 0.094093 -0.285338 0.061 Uiso 1 1 calc R N0BA N -0.6446(8) 0.3007(15) 0.7033(17) 0.160(7) 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 I1 0.0548(3) 0.0380(3) 0.0989(6) 0.0057(6) 0.0171(5) 0.0104(3) S2 0.0517(13) 0.0343(12) 0.0617(19) 0.0072(14) -0.0073(12) -0.0050(11) C4 0.051(4) 0.031(4) 0.057(7) 0.001(6) 0.007(6) 0.001(3) C5 0.041(4) 0.030(4) 0.045(5) -0.009(6) 0.004(6) 0.007(3) O7 0.055(4) 0.059(5) 0.119(8) -0.033(5) 0.036(5) -0.016(4) C8 0.037(4) 0.028(4) 0.043(7) 0.002(4) -0.002(4) 0.006(3) C9 0.056(6) 0.035(5) 0.061(7) -0.005(5) 0.016(5) -0.001(5) C10 0.071(6) 0.046(5) 0.066(7) -0.005(8) 0.031(7) -0.005(4) C11 0.057(6) 0.036(5) 0.056(7) -0.004(5) 0.006(5) 0.005(5) C12 0.064(7) 0.065(7) 0.067(9) -0.002(7) -0.007(6) -0.020(6) C13 0.045(5) 0.027(5) 0.055(7) -0.013(5) 0.009(4) -0.002(4) C15 0.047(5) 0.030(4) 0.052(6) -0.004(4) 0.012(4) -0.004(4) C16 0.049(5) 0.022(4) 0.039(6) -0.006(4) -0.009(4) -0.001(4) C17 0.052(5) 0.032(5) 0.064(7) 0.001(5) 0.010(5) 0.001(4) C19 0.050(5) 0.024(4) 0.044(6) 0.000(4) 0.002(4) -0.003(4) C23 0.050(5) 0.034(5) 0.047(7) 0.002(5) 0.006(5) -0.004(4) C25 0.040(5) 0.047(6) 0.061(7) 0.001(6) 0.003(5) -0.010(4) N27 0.049(4) 0.028(4) 0.043(5) 0.001(4) 0.003(4) -0.009(3) C29 0.054(7) 0.146(14) 0.139(15) 0.034(13) -0.011(8) -0.037(9) O35 0.049(4) 0.040(4) 0.091(6) 0.009(4) -0.006(4) 0.004(3) O37 0.099(5) 0.054(4) 0.050(6) 0.002(4) -0.011(4) -0.028(4) C38 0.053(5) 0.028(5) 0.054(7) -0.003(5) -0.002(5) 0.000(4) C40 0.037(4) 0.031(5) 0.049(6) -0.009(5) 0.000(4) -0.001(4) C3 0.066(6) 0.044(5) 0.051(8) -0.008(6) 0.010(6) 0.011(4) C0AA 0.052(5) 0.021(4) 0.053(7) -0.011(5) 0.003(5) 0.003(4) C2AA 0.046(6) 0.074(8) 0.105(12) 0.012(8) 0.023(7) 0.003(6) C1AA 0.042(6) 0.069(8) 0.080(10) 0.022(8) -0.003(6) -0.011(6) C4AA 0.118(10) 0.045(6) 0.040(7) -0.005(6) 0.012(7) 0.013(7) C6 0.089(8) 0.057(7) 0.065(8) -0.008(6) 0.030(7) 0.015(7) C5AA 0.077(7) 0.073(8) 0.065(9) -0.009(7) -0.004(6) -0.001(7) C3AA 0.048(5) 0.032(5) 0.049(7) -0.003(5) 0.014(4) -0.005(4) C6AA 0.091(8) 0.050(7) 0.060(8) -0.006(6) 0.019(6) -0.008(6) C7AA 0.047(5) 0.048(6) 0.061(7) 0.005(6) 0.014(5) 0.002(5) C9AA 0.144(13) 0.091(11) 0.062(10) -0.012(9) 0.006(10) 0.025(10) C8AA 0.061(6) 0.037(5) 0.056(7) 0.007(5) 0.006(5) -0.004(5) N0BA 0.26(2) 0.132(12) 0.089(12) -0.074(12) -0.012(12) 0.014(13) 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N27 S2 C23 108.0(4) O35 S2 C23 107.4(4) O35 S2 N27 105.8(4) O37 S2 C23 107.2(5) O37 S2 N27 106.5(4) O37 S2 O35 121.4(5) C16 C4 H4 119.7 C8AA C4 H4 119.7 C8AA C4 C16 120.7(8) C11 C5 C16 118.5(8) C11 C5 C19 122.8(7) C16 C5 C19 118.8(9) C17 C8 H8 108.6 C17 C8 C19 110.2(7) C17 C8 C38 111.4(7) C19 C8 H8 108.6 C19 C8 C38 109.5(7) C38 C8 H8 108.6 O7 C9 C13 119.8(10) O7 C9 C15 121.4(9) C15 C9 C13 118.7(8) C15 C10 H10 119.8 C6 C10 H10 119.8 C6 C10 C15 120.4(10) C5 C11 H11 119.4 C7AA C11 C5 121.1(9) C7AA C11 H11 119.4 C25 C12 H12 118.8 C1AA C12 H12 118.8 C1AA C12 C25 122.4(12) C40 C13 C9 121.0(8) C0AA C13 C9 119.9(8) C0AA C13 C40 119.1(8) C10 C15 C9 118.3(9) C3 C15 C9 122.4(8) C3 C15 C10 119.3(9) C4 C16 C5 119.7(9) C4 C16 C0AA 121.6(8) C0AA C16 C5 118.6(8) I1 C17 H17A 109.0 I1 C17 H17B 109.0 C8 C17 I1 113.1(6) C8 C17 H17A 109.0 C8 C17 H17B 109.0 H17A C17 H17B 107.8 C5 C19 C8 119.2(8) C40 C19 C5 120.2(8) C40 C19 C8 120.5(8) C25 C23 S2 120.5(7) C25 C23 C6AA 118.0(9) C6AA C23 S2 121.5(9) C12 C25 C23 120.8(10) C12 C25 H25 119.6 C23 C25 H25 119.6 C38 N27 S2 119.1(6) C38 N27 C3AA 112.7(7) C3AA N27 S2 115.8(6) H29A C29 H29B 109.5 H29A C29 H29C 109.5 H29B C29 H29C 109.5 C1AA C29 H29A 109.5 C1AA C29 H29B 109.5 C1AA C29 H29C 109.5 C8 C38 H38A 110.2 C8 C38 H38B 110.2 N27 C38 C8 107.7(7) N27 C38 H38A 110.2 N27 C38 H38B 110.2 H38A C38 H38B 108.5 C13 C40 C3AA 117.3(8) C19 C40 C13 119.9(8) C19 C40 C3AA 122.7(8) C15 C3 H3 119.4 C15 C3 C5AA 121.2(10) C5AA C3 H3 119.4 C13 C0AA C16 123.2(8) C13 C0AA H0AA 118.4 C16 C0AA H0AA 118.4 C1AA C2AA H2AA 119.3 C1AA C2AA C6AA 121.4(11) C6AA C2AA H2AA 119.3 C12 C1AA C29 121.8(13) C12 C1AA C2AA 117.5(10) C2AA C1AA C29 120.6(12) C6 C4AA C9AA 119.7(12) C5AA C4AA C6 121.2(11) C5AA C4AA C9AA 119.0(13) C10 C6 C4AA 118.8(10) C10 C6 H6 120.6 C4AA C6 H6 120.6 C3 C5AA H5AA 120.5 C4AA C5AA C3 119.0(11) C4AA C5AA H5AA 120.5 N27 C3AA C40 109.5(7) N27 C3AA H3AA 109.8 N27 C3AA H3AB 109.8 C40 C3AA H3AA 109.8 C40 C3AA H3AB 109.8 H3AA C3AA H3AB 108.2 C23 C6AA H6AA 120.1 C2AA C6AA C23 119.8(12) C2AA C6AA H6AA 120.1 C11 C7AA H7AA 119.9 C11 C7AA C8AA 120.2(9) C8AA C7AA H7AA 119.9 N0BA C9AA C4AA 179(2) C4 C8AA C7AA 119.8(9) C4 C8AA H8AA 120.1 C7AA C8AA H8AA 120.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance I1 C17 2.153(9) S2 C23 1.750(9) S2 N27 1.647(7) S2 O35 1.438(7) S2 O37 1.423(7) C4 H4 0.9300 C4 C16 1.397(12) C4 C8AA 1.369(15) C5 C11 1.394(14) C5 C16 1.414(10) C5 C19 1.457(12) O7 C9 1.214(11) C8 H8 0.9800 C8 C17 1.516(11) C8 C19 1.521(11) C8 C38 1.527(11) C9 C13 1.501(13) C9 C15 1.482(12) C10 H10 0.9300 C10 C15 1.396(12) C10 C6 1.375(17) C11 H11 0.9300 C11 C7AA 1.371(13) C12 H12 0.9300 C12 C25 1.369(12) C12 C1AA 1.362(15) C13 C40 1.440(11) C13 C0AA 1.359(12) C15 C3 1.361(12) C16 C0AA 1.406(12) C17 H17A 0.9700 C17 H17B 0.9700 C19 C40 1.378(13) C23 C25 1.378(13) C23 C6AA 1.397(14) C25 H25 0.9300 N27 C38 1.449(12) N27 C3AA 1.464(11) C29 H29A 0.9600 C29 H29B 0.9600 C29 H29C 0.9600 C29 C1AA 1.495(15) C38 H38A 0.9700 C38 H38B 0.9700 C40 C3AA 1.533(13) C3 H3 0.9300 C3 C5AA 1.378(14) C0AA H0AA 0.9300 C2AA H2AA 0.9300 C2AA C1AA 1.384(17) C2AA C6AA 1.391(15) C4AA C6 1.384(16) C4AA C5AA 1.372(15) C4AA C9AA 1.488(19) C6 H6 0.9300 C5AA H5AA 0.9300 C3AA H3AA 0.9700 C3AA H3AB 0.9700 C6AA H6AA 0.9300 C7AA H7AA 0.9300 C7AA C8AA 1.402(13) C9AA N0BA 1.092(17) C8AA H8AA 0.9300 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 S2 C23 C25 C12 176.6(8) S2 C23 C6AA C2AA -178.5(9) S2 N27 C38 C8 -147.5(5) S2 N27 C3AA C40 170.0(6) C4 C16 C0AA C13 176.1(9) C5 C11 C7AA C8AA 0.6(16) C5 C16 C0AA C13 -3.8(14) C5 C19 C40 C13 -0.7(14) C5 C19 C40 C3AA -179.8(9) O7 C9 C13 C40 -44.2(15) O7 C9 C13 C0AA 133.4(10) O7 C9 C15 C10 -22.7(15) O7 C9 C15 C3 154.6(11) C8 C19 C40 C13 -179.7(8) C8 C19 C40 C3AA 1.2(14) C9 C13 C40 C19 175.3(9) C9 C13 C40 C3AA -5.6(14) C9 C13 C0AA C16 -173.0(9) C9 C15 C3 C5AA -178.1(9) C10 C15 C3 C5AA -0.9(15) C11 C5 C16 C4 -0.3(14) C11 C5 C16 C0AA 179.6(9) C11 C5 C19 C8 1.6(14) C11 C5 C19 C40 -177.4(10) C11 C7AA C8AA C4 -0.6(16) C13 C9 C15 C10 154.5(10) C13 C9 C15 C3 -28.2(14) C13 C40 C3AA N27 -167.8(8) C15 C9 C13 C40 138.6(9) C15 C9 C13 C0AA -43.8(14) C15 C10 C6 C4AA -0.2(18) C15 C3 C5AA C4AA -0.4(16) C16 C4 C8AA C7AA 0.2(16) C16 C5 C11 C7AA -0.2(15) C16 C5 C19 C8 -179.4(8) C16 C5 C19 C40 1.6(14) C17 C8 C19 C5 78.1(11) C17 C8 C19 C40 -102.8(10) C17 C8 C38 N27 68.1(9) C19 C5 C11 C7AA 178.8(9) C19 C5 C16 C4 -179.3(9) C19 C5 C16 C0AA 0.5(13) C19 C8 C17 I1 -172.2(6) C19 C8 C38 N27 -54.0(9) C19 C40 C3AA N27 11.4(13) C23 S2 N27 C38 -73.4(8) C23 S2 N27 C3AA 65.9(8) C25 C12 C1AA C29 179.6(12) C25 C12 C1AA C2AA -1.1(18) C25 C23 C6AA C2AA 1.4(16) N27 S2 C23 C25 81.0(8) N27 S2 C23 C6AA -99.1(9) O35 S2 C23 C25 -32.7(9) O35 S2 C23 C6AA 147.1(9) O35 S2 N27 C38 41.4(8) O35 S2 N27 C3AA -179.3(7) O37 S2 C23 C25 -164.6(8) O37 S2 C23 C6AA 15.2(10) O37 S2 N27 C38 171.7(7) O37 S2 N27 C3AA -48.9(8) C38 C8 C17 I1 66.1(9) C38 C8 C19 C5 -159.0(9) C38 C8 C19 C40 20.0(12) C38 N27 C3AA C40 -48.2(10) C40 C13 C0AA C16 4.7(15) C0AA C13 C40 C19 -2.4(14) C0AA C13 C40 C3AA 176.8(9) C1AA C12 C25 C23 3.3(17) C1AA C2AA C6AA C23 0.7(18) C6 C10 C15 C9 178.6(10) C6 C10 C15 C3 1.2(17) C6 C4AA C5AA C3 1.4(17) C5AA C4AA C6 C10 -1.1(18) C3AA N27 C38 C8 72.1(8) C6AA C23 C25 C12 -3.3(15) C6AA C2AA C1AA C12 -0.9(19) C6AA C2AA C1AA C29 178.4(12) C9AA C4AA C6 C10 178.9(11) C9AA C4AA C5AA C3 -178.6(11) C8AA C4 C16 C5 0.3(15) C8AA C4 C16 C0AA -179.6(9)