#------------------------------------------------------------------------------ #$Date: 2019-04-16 00:44:58 +0300 (Tue, 16 Apr 2019) $ #$Revision: 214635 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/08/1550883.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_1550883 loop_ _publ_author_name 'Almeida, Renata G.' 'Carvalho, Renato' 'Nunes, Mateus P.' 'Gomes, Roberto' 'Pedrosa, Leandro' 'Simone, Carlos' 'Elumalai, Gopi' 'Geertsen, Valerie' 'Gravel, Edmond' 'Doris, Eric' 'da Silva J\'unior, Eufr\^anio N.' _publ_section_title ; Carbon nanotube-ruthenium hybrid towards mild oxidation of sulfides to sulfones: Efficient synthesis of diverse sulfonyl compounds ; _journal_name_full 'Catalysis Science & Technology' _journal_paper_doi 10.1039/C9CY00384C _journal_year 2019 _chemical_formula_moiety 'C32 H29 B F2 N2 O S2' _chemical_formula_sum 'C32 H29 B F2 N2 O S2' _chemical_formula_weight 570.50 _chemical_name_systematic 'Carbon nanotube-ruthenium hybrids towards mild oxidation of sulfides to sulfones: Efficient synthesis of sulfonyl compounds with potential biological aplications.' _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'I -2ya' _space_group_name_H-M_alt 'I 1 a 1' _symmetry_space_group_name_Hall 'I -2ya' _symmetry_space_group_name_H-M 'I 1 a 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-02-11 _audit_creation_method ; Olex2 1.2-ac3 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2019-02-12 deposited with the CCDC. 2019-04-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.631(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.217(3) _cell_length_b 7.6976(8) _cell_length_c 20.1851(17) _cell_measurement_reflns_used 1624 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.9400 _cell_measurement_theta_min 3.2590 _cell_volume 2798.4(6) _computing_cell_refinement 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.884 _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 -67.00 118.00 1.00 131.51 -- 27.63 54.00 0.00 185 2 \w -68.00 -35.00 1.00 131.51 -- 27.63 54.00 120.00 33 ; _diffrn_measurement_device 'two-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Mini (ROW)' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0390699000 _diffrn_orient_matrix_UB_12 0.0077837000 _diffrn_orient_matrix_UB_13 -0.0090893000 _diffrn_orient_matrix_UB_21 0.0030563000 _diffrn_orient_matrix_UB_22 -0.0285300000 _diffrn_orient_matrix_UB_23 -0.0328503000 _diffrn_orient_matrix_UB_31 -0.0044425000 _diffrn_orient_matrix_UB_32 -0.0871669000 _diffrn_orient_matrix_UB_33 0.0100178000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_unetI/netI 0.0541 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.884 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 7979 _diffrn_reflns_point_group_measured_fraction_full 0.537 _diffrn_reflns_point_group_measured_fraction_max 0.461 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 34.500 _diffrn_reflns_theta_min 2.810 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.42410 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017) 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 1.354 _exptl_crystal_description block _exptl_crystal_F_000 1192 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.655 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.073 _refine_ls_abs_structure_details ; Classical Flack method preferred over Parsons because s.u. lower. ; _refine_ls_abs_structure_Flack 0.04(13) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 366 _refine_ls_number_reflns 5467 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all 0.1333 _refine_ls_R_factor_gt 0.0736 _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^)+(0.1319P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1863 _refine_ls_wR_factor_ref 0.2429 _reflns_Friedel_coverage 0.043 _reflns_Friedel_fraction_full 0.075 _reflns_Friedel_fraction_max 0.038 _reflns_number_gt 2881 _reflns_number_total 5467 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cy00384c2.cif _cod_data_source_block ensj787 _cod_database_code 1550883 _shelx_shelxl_version_number 2017/1 _chemical_oxdiff_formula 'C32 H29 B F2 N2 O S2' _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 0.961 _shelx_estimated_absorpt_t_min 0.944 _reflns_odcompleteness_completeness 99.74 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C009(H009), C00B(H00B), C00M(H00M), C00N(H00N), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00W(H00W), C00X(H00X), C00Z(H00Z), C010(H010), C012(H012), C013(H013) 2.b Idealised Me refined as rotating group: C00G(H00A,H00C,H00D), C00I(H00E,H00F,H00G), C00Y(H00H,H00I,H00J), C011(H01A, H01B,H01C), C014(H01D,H01E,H01F) ; _shelx_res_file ; TITL ensj787_b.res in Ia ensj787.res created by SHELXL-2017/1 at 09:42:15 on 11-Feb-2019 REM Old TITL ENSJ787 in I2/a REM SHELXT solution in Ia REM R1 0.183, Rweak 0.047, Alpha 0.003, Orientation as input REM Flack x = 0.415 ( 0.134 ) from Parsons' quotients REM Formula found by SHELXT: C31 N5 O2 S2 CELL 0.71073 18.2165 7.6976 20.1851 90 98.631 90 ZERR 4 0.0029 0.0008 0.0017 0 0.011 0 LATT -2 SYMM 0.5+X,-Y,+Z SFAC C H B F N O S UNIT 128 116 4 8 8 4 8 L.S. 10 PLAN 20 SIZE 0.25 0.2 0.17 TEMP 20(2) BOND $H LIST 6 fmap 2 acta REM REM REM WGHT 0.131900 FVAR 0.40725 S001 7 0.472572 0.661488 0.261524 11.00000 0.07187 0.07171 = 0.03919 0.00080 0.01744 -0.01031 S002 7 0.424316 0.341488 0.741537 11.00000 0.07081 0.07382 = 0.03552 -0.00075 0.01810 -0.01212 F003 4 0.394267 0.806151 0.523789 11.00000 0.11568 0.05294 = 0.08243 -0.00162 0.05115 0.00241 F004 4 0.312520 0.605132 0.478730 11.00000 0.05591 0.09869 = 0.06207 0.01598 0.01542 0.01078 C005 1 0.487444 0.480034 0.445403 11.00000 0.04610 0.04630 = 0.03868 -0.00345 0.01657 -0.01050 C006 1 0.469425 0.392438 0.558351 11.00000 0.04756 0.04207 = 0.04477 0.00071 0.02152 -0.00121 C007 1 0.513223 0.484957 0.383798 11.00000 0.05505 0.06263 = 0.03355 -0.00721 0.01504 -0.01353 C008 1 0.473034 0.615039 0.346288 11.00000 0.06650 0.06342 = 0.03820 0.00082 0.02160 -0.01081 C009 1 0.686403 0.115838 0.503952 11.00000 0.06797 0.06490 = 0.05317 -0.00132 0.00444 0.00410 AFIX 43 H009 2 0.737020 0.136837 0.506458 11.00000 -1.20000 AFIX 0 N00A 5 0.432604 0.607920 0.445309 11.00000 0.06118 0.05447 = 0.03952 0.00155 0.01775 -0.01171 C00B 1 0.307778 0.131438 0.685430 11.00000 0.08209 0.06753 = 0.05102 -0.00893 0.02362 -0.01152 AFIX 43 H00B 2 0.322502 0.149305 0.643793 11.00000 -1.20000 AFIX 0 O00C 6 0.700034 -0.194531 0.497571 11.00000 0.10324 0.07206 = 0.11027 -0.00507 0.02127 0.02508 C00D 1 0.345722 0.204112 0.741498 11.00000 0.05827 0.05350 = 0.04887 0.00801 0.01822 0.00849 N00E 5 0.413951 0.513996 0.558327 11.00000 0.05531 0.06339 = 0.03852 -0.00319 0.02085 -0.00386 C00F 1 0.481364 0.307285 0.620257 11.00000 0.05510 0.06004 = 0.04208 -0.00459 0.02013 -0.00983 C00G 1 0.370110 0.828257 0.366161 11.00000 0.11759 0.06225 = 0.07086 0.01400 0.04437 0.01547 AFIX 137 H00A 2 0.380415 0.883553 0.325930 11.00000 -1.50000 H00C 2 0.373700 0.912182 0.401681 11.00000 -1.50000 H00D 2 0.320898 0.780394 0.358663 11.00000 -1.50000 AFIX 0 C00H 1 0.561216 0.225337 0.501309 11.00000 0.05046 0.05198 = 0.04289 -0.00369 0.01573 -0.00658 C00I 1 0.570542 0.374895 0.358678 11.00000 0.06899 0.09486 = 0.04141 -0.00060 0.02148 0.00589 AFIX 137 H00E 2 0.617142 0.388317 0.387504 11.00000 -1.50000 H00F 2 0.575895 0.410179 0.314037 11.00000 -1.50000 H00G 2 0.555488 0.255340 0.358322 11.00000 -1.50000 AFIX 0 C00J 1 0.505972 0.372268 0.502056 11.00000 0.04776 0.04889 = 0.04107 -0.00066 0.01475 -0.00635 B00K 3 0.386434 0.638763 0.502065 11.00000 0.04609 0.04731 = 0.04429 -0.00110 0.01687 0.00095 C00L 1 0.424094 0.688616 0.384820 11.00000 0.07287 0.04875 = 0.04921 0.00625 0.02151 -0.00401 C00M 1 0.583869 -0.079367 0.494568 11.00000 0.07479 0.05553 = 0.07715 -0.00591 0.01611 -0.00357 AFIX 43 H00M 2 0.565429 -0.192126 0.490337 11.00000 -1.20000 AFIX 0 C00N 1 0.536250 0.057407 0.496787 11.00000 0.05989 0.06679 = 0.06911 -0.00518 0.01672 -0.00581 AFIX 43 H00N 2 0.485791 0.035720 0.495185 11.00000 -1.20000 AFIX 0 C00O 1 0.428938 0.380382 0.657133 11.00000 0.05980 0.05833 = 0.04000 -0.00143 0.02133 -0.00896 C00P 1 0.388214 0.508941 0.618869 11.00000 0.05549 0.06463 = 0.04214 -0.00106 0.01957 -0.00820 C00Q 1 0.225448 -0.004932 0.751947 11.00000 0.06890 0.08136 = 0.10054 0.01637 0.02558 -0.00190 AFIX 43 H00Q 2 0.184392 -0.074251 0.755443 11.00000 -1.20000 AFIX 0 C00R 1 0.245715 0.028567 0.691897 11.00000 0.06767 0.08390 = 0.08581 -0.01420 0.01404 -0.01843 AFIX 43 H00R 2 0.217825 -0.017727 0.653597 11.00000 -1.20000 AFIX 0 C00S 1 0.635958 0.255772 0.505620 11.00000 0.05074 0.06463 = 0.05424 -0.00287 0.01290 -0.00384 AFIX 43 H00S 2 0.653755 0.369105 0.509673 11.00000 -1.20000 AFIX 0 C00T 1 0.571470 0.818801 0.195948 11.00000 0.08658 0.09082 = 0.06030 0.01751 0.03552 0.00905 AFIX 43 H00T 2 0.543389 0.771731 0.157899 11.00000 -1.20000 AFIX 0 C00U 1 0.659561 -0.050159 0.498614 11.00000 0.07152 0.06451 = 0.05535 -0.00201 0.01353 0.01004 C00V 1 0.551907 0.790392 0.259658 11.00000 0.06420 0.04981 = 0.04715 0.00428 0.02693 0.00732 C00W 1 0.325528 0.173372 0.803441 11.00000 0.07362 0.06354 = 0.04168 0.00671 0.02301 0.00091 AFIX 43 H00W 2 0.351272 0.224727 0.841735 11.00000 -1.20000 AFIX 0 C00X 1 0.633604 0.918625 0.191122 11.00000 0.10937 0.08139 = 0.08677 0.01731 0.06369 0.00054 AFIX 43 H00X 2 0.647956 0.935551 0.149281 11.00000 -1.20000 AFIX 0 C00Y 1 0.328917 0.617327 0.636912 11.00000 0.06770 0.10207 = 0.04850 0.00733 0.02075 0.01421 AFIX 137 H00H 2 0.334188 0.733347 0.620825 11.00000 -1.50000 H00I 2 0.331608 0.619264 0.684770 11.00000 -1.50000 H00J 2 0.281799 0.570942 0.617056 11.00000 -1.50000 AFIX 0 C00Z 1 0.653402 0.967608 0.308081 11.00000 0.08900 0.08620 = 0.08181 -0.00121 0.02565 -0.00941 AFIX 43 H00Z 2 0.679698 1.020130 0.345864 11.00000 -1.20000 AFIX 0 C010 1 0.266269 0.064717 0.807378 11.00000 0.07275 0.11100 = 0.07259 0.03111 0.03379 -0.00238 AFIX 43 H010 2 0.253852 0.038275 0.849266 11.00000 -1.20000 AFIX 0 C011 1 0.537510 0.173984 0.645775 11.00000 0.08295 0.07614 = 0.06676 0.01239 0.02837 0.01224 AFIX 137 H01A 2 0.516723 0.060257 0.636877 11.00000 -1.50000 H01B 2 0.551723 0.188620 0.693196 11.00000 -1.50000 H01C 2 0.580374 0.186918 0.623743 11.00000 -1.50000 AFIX 0 C012 1 0.594643 0.866861 0.314898 11.00000 0.06809 0.07761 = 0.06204 -0.00079 0.02547 -0.00950 AFIX 43 H012 2 0.582350 0.847962 0.357398 11.00000 -1.20000 AFIX 0 C013 1 0.675396 0.994733 0.247393 11.00000 0.07401 0.08405 = 0.11113 0.01584 0.04619 -0.00794 AFIX 43 H013 2 0.716973 1.061873 0.243483 11.00000 -1.20000 AFIX 0 C014 1 0.778372 -0.168940 0.490125 11.00000 0.10739 0.13986 = 0.09953 0.02086 0.04068 0.06524 AFIX 137 H01D 2 0.781283 -0.115490 0.447627 11.00000 -1.50000 H01E 2 0.803163 -0.279309 0.492398 11.00000 -1.50000 H01F 2 0.801815 -0.095313 0.525488 11.00000 -1.50000 AFIX 0 HKLF 4 REM ensj787_b.res in Ia REM R1 = 0.0736 for 2881 Fo > 4sig(Fo) and 0.1333 for all 5467 data REM 366 parameters refined using 2 restraints END WGHT 0.1319 0.0000 REM Highest difference peak 0.655, deepest hole -0.398, 1-sigma level 0.073 Q1 1 0.5783 0.3975 0.5212 11.00000 0.05 0.66 Q2 1 0.5033 0.2052 0.4755 11.00000 0.05 0.61 Q3 1 0.7522 0.2513 0.4913 11.00000 0.05 0.47 Q4 1 0.3225 0.7731 0.4914 11.00000 0.05 0.47 Q5 1 0.7063 0.1310 0.4999 11.00000 0.05 0.36 Q6 1 0.7266 -0.0508 0.5026 11.00000 0.05 0.34 Q7 1 0.3572 0.9544 0.5112 11.00000 0.05 0.34 Q8 1 0.4728 0.3445 0.5906 11.00000 0.05 0.30 Q9 1 0.5019 0.5056 0.3723 11.00000 0.05 0.30 Q10 1 0.4360 0.3288 0.6554 11.00000 0.05 0.30 Q11 1 0.5582 0.8023 0.2285 11.00000 0.05 0.27 Q12 1 0.4358 0.4798 0.7493 11.00000 0.05 0.27 Q13 1 0.4755 0.6215 0.3030 11.00000 0.05 0.27 Q14 1 0.4096 0.7184 0.3779 11.00000 0.05 0.27 Q15 1 0.4422 0.4197 0.5521 11.00000 0.05 0.26 Q16 1 0.4233 0.6751 0.4153 11.00000 0.05 0.25 Q17 1 0.6106 -0.1856 0.5117 11.00000 0.05 0.24 Q18 1 0.6325 0.0837 0.4962 11.00000 0.05 0.23 Q19 1 0.4648 0.6660 0.3508 11.00000 0.05 0.23 Q20 1 0.6997 -0.3288 0.4997 11.00000 0.05 0.22 ; _shelx_res_checksum 83995 _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 1.763 _oxdiff_exptl_absorpt_empirical_full_min 0.686 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y, z' 'x+1/2, y+1/2, z+1/2' 'x+1, -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 S001 S 0.47257(7) 0.6615(2) 0.26152(6) 0.0600(4) Uani 1 1 d . S002 S 0.42432(7) 0.3415(2) 0.74154(6) 0.0590(4) Uani 1 1 d . F003 F 0.3943(3) 0.8062(4) 0.5238(2) 0.0800(11) Uani 1 1 d . F004 F 0.3125(2) 0.6051(5) 0.47873(18) 0.0716(9) Uani 1 1 d . C005 C 0.4874(3) 0.4800(7) 0.4454(2) 0.0427(10) Uani 1 1 d . C006 C 0.4694(3) 0.3924(6) 0.5584(3) 0.0433(10) Uani 1 1 d . C007 C 0.5132(3) 0.4850(7) 0.3838(2) 0.0495(12) Uani 1 1 d . C008 C 0.4730(3) 0.6150(8) 0.3463(3) 0.0546(14) Uani 1 1 d . C009 C 0.6864(4) 0.1158(7) 0.5040(4) 0.0625(15) Uani 1 1 d . H009 H 0.737020 0.136837 0.506458 0.075 Uiso 1 1 calc R N00A N 0.4326(3) 0.6079(6) 0.4453(2) 0.0507(11) Uani 1 1 d . C00B C 0.3078(4) 0.1314(9) 0.6854(3) 0.0655(17) Uani 1 1 d . H00B H 0.322502 0.149305 0.643793 0.079 Uiso 1 1 calc R O00C O 0.7000(4) -0.1945(6) 0.4976(4) 0.0947(15) Uani 1 1 d . C00D C 0.3457(3) 0.2041(8) 0.7415(3) 0.0525(13) Uani 1 1 d . N00E N 0.4140(2) 0.5140(7) 0.5583(2) 0.0510(11) Uani 1 1 d . C00F C 0.4814(3) 0.3073(8) 0.6203(3) 0.0511(13) Uani 1 1 d . C00G C 0.3701(5) 0.8283(9) 0.3662(4) 0.080(2) Uani 1 1 d . H00A H 0.380415 0.883553 0.325930 0.121 Uiso 1 1 calc GR H00C H 0.373700 0.912182 0.401681 0.121 Uiso 1 1 calc GR H00D H 0.320898 0.780394 0.358663 0.121 Uiso 1 1 calc GR C00H C 0.5612(3) 0.2253(6) 0.5013(2) 0.0475(10) Uani 1 1 d . C00I C 0.5705(4) 0.3749(11) 0.3587(3) 0.0671(17) Uani 1 1 d . H00E H 0.617142 0.388317 0.387504 0.101 Uiso 1 1 calc GR H00F H 0.575895 0.410179 0.314037 0.101 Uiso 1 1 calc GR H00G H 0.555488 0.255340 0.358322 0.101 Uiso 1 1 calc GR C00J C 0.5060(3) 0.3723(7) 0.5021(3) 0.0451(11) Uani 1 1 d . B00K B 0.3864(4) 0.6388(8) 0.5021(3) 0.0449(13) Uani 1 1 d . C00L C 0.4241(4) 0.6886(7) 0.3848(3) 0.0557(14) Uani 1 1 d . C00M C 0.5839(4) -0.0794(8) 0.4946(3) 0.0687(15) Uani 1 1 d . H00M H 0.565429 -0.192126 0.490337 0.082 Uiso 1 1 calc R C00N C 0.5363(4) 0.0574(8) 0.4968(3) 0.0645(14) Uani 1 1 d . H00N H 0.485791 0.035720 0.495185 0.077 Uiso 1 1 calc R C00O C 0.4289(3) 0.3804(8) 0.6571(3) 0.0513(13) Uani 1 1 d . C00P C 0.3882(3) 0.5089(8) 0.6189(3) 0.0528(13) Uani 1 1 d . C00Q C 0.2254(4) -0.0049(12) 0.7519(4) 0.082(2) Uani 1 1 d . H00Q H 0.184392 -0.074251 0.755443 0.099 Uiso 1 1 calc R C00R C 0.2457(4) 0.0286(10) 0.6919(4) 0.079(2) Uani 1 1 d . H00R H 0.217825 -0.017727 0.653597 0.095 Uiso 1 1 calc R C00S C 0.6360(3) 0.2558(8) 0.5056(3) 0.0560(12) Uani 1 1 d . H00S H 0.653755 0.369105 0.509673 0.067 Uiso 1 1 calc R C00T C 0.5715(5) 0.8188(11) 0.1959(4) 0.077(2) Uani 1 1 d . H00T H 0.543389 0.771731 0.157899 0.092 Uiso 1 1 calc R C00U C 0.6596(4) -0.0502(8) 0.4986(3) 0.0634(14) Uani 1 1 d . C00V C 0.5519(3) 0.7904(8) 0.2597(3) 0.0518(13) Uani 1 1 d . C00W C 0.3255(4) 0.1734(8) 0.8034(3) 0.0581(14) Uani 1 1 d . H00W H 0.351272 0.224727 0.841735 0.070 Uiso 1 1 calc R C00X C 0.6336(5) 0.9186(10) 0.1911(5) 0.087(2) Uani 1 1 d . H00X H 0.647956 0.935551 0.149281 0.105 Uiso 1 1 calc R C00Y C 0.3289(4) 0.6173(11) 0.6369(3) 0.0715(18) Uani 1 1 d . H00H H 0.334188 0.733347 0.620825 0.107 Uiso 1 1 calc GR H00I H 0.331608 0.619264 0.684770 0.107 Uiso 1 1 calc GR H00J H 0.281799 0.570942 0.617056 0.107 Uiso 1 1 calc GR C00Z C 0.6534(5) 0.9676(11) 0.3081(4) 0.084(2) Uani 1 1 d . H00Z H 0.679698 1.020130 0.345864 0.101 Uiso 1 1 calc R C010 C 0.2663(4) 0.0647(12) 0.8074(4) 0.083(2) Uani 1 1 d . H010 H 0.253852 0.038275 0.849266 0.100 Uiso 1 1 calc R C011 C 0.5375(5) 0.1740(9) 0.6458(4) 0.0735(18) Uani 1 1 d . H01A H 0.516723 0.060257 0.636877 0.110 Uiso 1 1 calc GR H01B H 0.551723 0.188620 0.693196 0.110 Uiso 1 1 calc GR H01C H 0.580374 0.186918 0.623743 0.110 Uiso 1 1 calc GR C012 C 0.5946(4) 0.8669(10) 0.3149(4) 0.0676(17) Uani 1 1 d . H012 H 0.582350 0.847962 0.357398 0.081 Uiso 1 1 calc R C013 C 0.6754(5) 0.9947(13) 0.2474(5) 0.086(2) Uani 1 1 d . H013 H 0.716973 1.061873 0.243483 0.104 Uiso 1 1 calc R C014 C 0.7784(6) -0.1689(14) 0.4901(5) 0.113(3) Uani 1 1 d . H01D H 0.781283 -0.115490 0.447627 0.170 Uiso 1 1 calc GR H01E H 0.803163 -0.279309 0.492398 0.170 Uiso 1 1 calc GR H01F H 0.801815 -0.095313 0.525488 0.170 Uiso 1 1 calc GR 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 S001 0.0719(9) 0.0717(9) 0.0392(6) 0.0008(6) 0.0174(6) -0.0103(7) S002 0.0708(9) 0.0738(10) 0.0355(6) -0.0007(6) 0.0181(5) -0.0121(7) F003 0.116(3) 0.0529(18) 0.082(2) -0.0016(17) 0.051(2) 0.002(2) F004 0.0559(18) 0.099(2) 0.0621(19) 0.0160(18) 0.0154(14) 0.0108(18) C005 0.046(2) 0.046(3) 0.039(2) -0.003(2) 0.0166(18) -0.010(2) C006 0.048(3) 0.042(3) 0.045(3) 0.001(2) 0.022(2) -0.001(2) C007 0.055(3) 0.063(3) 0.034(2) -0.007(2) 0.0150(19) -0.014(3) C008 0.067(4) 0.063(3) 0.038(3) 0.001(2) 0.022(2) -0.011(3) C009 0.068(4) 0.065(3) 0.053(3) -0.001(3) 0.004(3) 0.004(3) N00A 0.061(3) 0.054(3) 0.040(2) 0.002(2) 0.0178(19) -0.012(2) C00B 0.082(5) 0.068(4) 0.051(3) -0.009(3) 0.024(3) -0.012(3) O00C 0.103(4) 0.072(2) 0.110(4) -0.005(4) 0.021(3) 0.025(4) C00D 0.058(3) 0.053(3) 0.049(3) 0.008(3) 0.018(2) 0.008(3) N00E 0.055(3) 0.063(3) 0.039(2) -0.003(2) 0.0208(18) -0.004(2) C00F 0.055(3) 0.060(3) 0.042(3) -0.005(2) 0.020(2) -0.010(2) C00G 0.118(6) 0.062(4) 0.071(4) 0.014(3) 0.044(4) 0.015(4) C00H 0.050(2) 0.052(2) 0.043(2) -0.004(2) 0.0157(17) -0.007(2) C00I 0.069(4) 0.095(5) 0.041(3) -0.001(3) 0.021(2) 0.006(3) C00J 0.048(3) 0.049(3) 0.041(2) -0.001(2) 0.015(2) -0.006(2) B00K 0.046(3) 0.047(3) 0.044(3) -0.001(2) 0.017(2) 0.001(2) C00L 0.073(4) 0.049(3) 0.049(3) 0.006(3) 0.022(3) -0.004(3) C00M 0.075(4) 0.056(3) 0.077(4) -0.006(3) 0.016(3) -0.004(3) C00N 0.060(3) 0.067(3) 0.069(3) -0.005(3) 0.017(3) -0.006(3) C00O 0.060(3) 0.058(3) 0.040(3) -0.001(2) 0.021(2) -0.009(3) C00P 0.055(3) 0.065(3) 0.042(2) -0.001(3) 0.020(2) -0.008(3) C00Q 0.069(4) 0.081(5) 0.101(6) 0.016(4) 0.026(4) -0.002(4) C00R 0.068(4) 0.084(5) 0.086(5) -0.014(4) 0.014(4) -0.018(4) C00S 0.051(3) 0.065(3) 0.054(3) -0.003(2) 0.013(2) -0.004(2) C00T 0.087(5) 0.091(5) 0.060(4) 0.018(4) 0.036(4) 0.009(4) C00U 0.072(4) 0.065(3) 0.055(3) -0.002(3) 0.014(2) 0.010(3) C00V 0.064(3) 0.050(3) 0.047(3) 0.004(2) 0.027(2) 0.007(3) C00W 0.074(4) 0.064(3) 0.042(3) 0.007(2) 0.023(3) 0.001(3) C00X 0.109(6) 0.081(5) 0.087(5) 0.017(4) 0.064(5) 0.001(5) C00Y 0.068(4) 0.102(5) 0.048(3) 0.007(3) 0.021(3) 0.014(4) C00Z 0.089(5) 0.086(5) 0.082(5) -0.001(4) 0.026(4) -0.009(5) C010 0.073(4) 0.111(6) 0.073(4) 0.031(4) 0.034(3) -0.002(4) C011 0.083(5) 0.076(4) 0.067(4) 0.012(3) 0.028(3) 0.012(3) C012 0.068(4) 0.078(4) 0.062(4) -0.001(3) 0.025(3) -0.009(3) C013 0.074(4) 0.084(5) 0.111(7) 0.016(5) 0.046(4) -0.008(4) C014 0.107(7) 0.140(8) 0.100(6) 0.021(6) 0.041(5) 0.065(6) 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' B B 0.0013 0.0007 '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' 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 C008 S001 C00V 104.7(3) C00O S002 C00D 105.0(3) C007 C005 N00A 108.4(4) C007 C005 C00J 131.8(5) N00A C005 C00J 119.8(4) N00E C006 C00F 109.5(4) N00E C006 C00J 120.7(5) C00F C006 C00J 129.8(5) C005 C007 C008 106.5(5) C005 C007 C00I 129.4(5) C008 C007 C00I 124.1(5) C007 C008 S001 127.1(5) C00L C008 S001 123.8(5) C00L C008 C007 108.5(5) C00S C009 H009 120.5 C00U C009 H009 120.5 C00U C009 C00S 119.1(6) C005 N00A B00K 125.2(4) C00L N00A C005 107.9(5) C00L N00A B00K 126.7(5) C00D C00B H00B 120.9 C00D C00B C00R 118.2(6) C00R C00B H00B 120.9 C00U O00C C014 115.9(6) C00B C00D S002 123.7(5) C00B C00D C00W 121.0(6) C00W C00D S002 115.3(5) C006 N00E B00K 126.3(4) C00P N00E C006 109.2(5) C00P N00E B00K 124.5(5) C006 C00F C00O 104.9(5) C006 C00F C011 129.8(5) C00O C00F C011 125.3(5) H00A C00G H00C 109.5 H00A C00G H00D 109.5 H00C C00G H00D 109.5 C00L C00G H00A 109.5 C00L C00G H00C 109.5 C00L C00G H00D 109.5 C00N C00H C00J 119.4(5) C00N C00H C00S 118.8(5) C00S C00H C00J 121.8(5) C007 C00I H00E 109.5 C007 C00I H00F 109.5 C007 C00I H00G 109.5 H00E C00I H00F 109.5 H00E C00I H00G 109.5 H00F C00I H00G 109.5 C005 C00J C00H 120.6(4) C006 C00J C005 120.3(5) C006 C00J C00H 119.0(5) F003 B00K F004 109.7(5) F003 B00K N00A 110.1(5) F003 B00K N00E 110.6(5) F004 B00K N00A 109.3(5) F004 B00K N00E 109.4(5) N00E B00K N00A 107.7(5) C008 C00L C00G 128.1(6) N00A C00L C008 108.7(5) N00A C00L C00G 123.2(6) C00N C00M H00M 119.9 C00N C00M C00U 120.2(6) C00U C00M H00M 119.9 C00H C00N C00M 121.5(6) C00H C00N H00N 119.2 C00M C00N H00N 119.2 C00F C00O S002 125.6(5) C00P C00O S002 124.2(4) C00P C00O C00F 109.6(5) N00E C00P C00O 106.7(5) N00E C00P C00Y 124.9(5) C00O C00P C00Y 128.4(5) C00R C00Q H00Q 120.8 C00R C00Q C010 118.5(7) C010 C00Q H00Q 120.8 C00B C00R H00R 119.1 C00Q C00R C00B 121.8(7) C00Q C00R H00R 119.1 C009 C00S H00S 119.7 C00H C00S C009 120.6(5) C00H C00S H00S 119.7 C00V C00T H00T 120.8 C00X C00T H00T 120.8 C00X C00T C00V 118.3(8) C009 C00U C00M 119.8(6) O00C C00U C009 126.0(7) O00C C00U C00M 114.2(6) C00T C00V S001 115.5(6) C012 C00V S001 125.8(4) C012 C00V C00T 118.7(7) C00D C00W H00W 120.8 C00D C00W C010 118.4(7) C010 C00W H00W 120.8 C00T C00X H00X 119.1 C00T C00X C013 121.8(7) C013 C00X H00X 119.1 C00P C00Y H00H 109.5 C00P C00Y H00I 109.5 C00P C00Y H00J 109.5 H00H C00Y H00I 109.5 H00H C00Y H00J 109.5 H00I C00Y H00J 109.5 C012 C00Z H00Z 119.1 C012 C00Z C013 121.8(9) C013 C00Z H00Z 119.1 C00Q C010 C00W 122.0(7) C00Q C010 H010 119.0 C00W C010 H010 119.0 C00F C011 H01A 109.5 C00F C011 H01B 109.5 C00F C011 H01C 109.5 H01A C011 H01B 109.5 H01A C011 H01C 109.5 H01B C011 H01C 109.5 C00V C012 H012 119.3 C00Z C012 C00V 121.3(7) C00Z C012 H012 119.3 C00X C013 H013 121.0 C00Z C013 C00X 118.0(8) C00Z C013 H013 121.0 O00C C014 H01D 109.5 O00C C014 H01E 109.5 O00C C014 H01F 109.5 H01D C014 H01E 109.5 H01D C014 H01F 109.5 H01E C014 H01F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S001 C008 1.747(6) S001 C00V 1.758(6) S002 C00D 1.780(6) S002 C00O 1.744(5) F003 B00K 1.362(7) F004 B00K 1.383(8) C005 C007 1.394(7) C005 N00A 1.402(7) C005 C00J 1.412(7) C006 N00E 1.377(7) C006 C00F 1.399(8) C006 C00J 1.409(7) C007 C008 1.395(9) C007 C00I 1.491(9) C008 C00L 1.389(9) C009 H009 0.9300 C009 C00S 1.420(8) C009 C00U 1.367(8) N00A B00K 1.538(8) N00A C00L 1.358(8) C00B H00B 0.9300 C00B C00D 1.355(9) C00B C00R 1.402(9) O00C C00U 1.336(8) O00C C014 1.470(13) C00D C00W 1.376(8) N00E B00K 1.514(8) N00E C00P 1.374(6) C00F C00O 1.413(8) C00F C011 1.485(9) C00G H00A 0.9600 C00G H00C 0.9600 C00G H00D 0.9600 C00G C00L 1.467(10) C00H C00J 1.515(8) C00H C00N 1.369(8) C00H C00S 1.371(7) C00I H00E 0.9600 C00I H00F 0.9600 C00I H00G 0.9600 C00M H00M 0.9300 C00M C00N 1.369(9) C00M C00U 1.387(10) C00N H00N 0.9300 C00O C00P 1.398(8) C00P C00Y 1.454(9) C00Q H00Q 0.9300 C00Q C00R 1.344(11) C00Q C010 1.357(12) C00R H00R 0.9300 C00S H00S 0.9300 C00T H00T 0.9300 C00T C00V 1.402(9) C00T C00X 1.384(12) C00V C012 1.391(10) C00W H00W 0.9300 C00W C010 1.377(10) C00X H00X 0.9300 C00X C013 1.398(14) C00Y H00H 0.9600 C00Y H00I 0.9600 C00Y H00J 0.9600 C00Z H00Z 0.9300 C00Z C012 1.345(10) C00Z C013 1.361(12) C010 H010 0.9300 C011 H01A 0.9600 C011 H01B 0.9600 C011 H01C 0.9600 C012 H012 0.9300 C013 H013 0.9300 C014 H01D 0.9600 C014 H01E 0.9600 C014 H01F 0.9600