#------------------------------------------------------------------------------ #$Date: 2019-04-16 00:44:58 +0300 (Tue, 16 Apr 2019) $ #$Revision: 214635 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/08/1550882.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_1550882 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_sum 'C20 H11 Br O2 S' _chemical_formula_weight 395.26 _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 triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-02-20 deposited with the CCDC. 2019-04-15 downloaded from the CCDC. ; _cell_angle_alpha 106.280(10) _cell_angle_beta 102.659(10) _cell_angle_gamma 90.396(8) _cell_formula_units_Z 2 _cell_length_a 8.0446(8) _cell_length_b 9.3059(9) _cell_length_c 11.5017(15) _cell_measurement_reflns_used 1973 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 31.6 _cell_measurement_theta_min 3.31 _cell_volume 804.28(16) _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 0.851 _diffrn_measurement_device 'two-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Mini (ROW)' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_unetI/netI 0.0518 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.851 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 7235 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.851 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 34.472 _diffrn_reflns_theta_min 2.602 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 2.694 _exptl_absorpt_correction_T_max 1.39 _exptl_absorpt_correction_T_min 0.85 _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 colorless _exptl_crystal_density_diffrn 1.632 _exptl_crystal_description prism _exptl_crystal_F_000 396 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.442 _refine_diff_density_min -0.545 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 5790 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.1078 _refine_ls_R_factor_gt 0.0510 _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^)+(0.0586P)^2^+0.0697P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1194 _refine_ls_wR_factor_ref 0.1548 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3064 _reflns_number_total 5790 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cy00384c2.cif _cod_data_source_block C3265-2-R _cod_database_code 1550882 _shelx_shelxl_version_number 2014/7 _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 ; shelx.res created by SHELXL-2014/7 TITL c3265-2-r_a.res in P-1 CELL 0.71073 8.0446 9.3059 11.5017 106.280 102.659 90.396 ZERR 2.00 0.0008 0.0009 0.0015 0.010 0.010 0.008 LATT 1 SFAC C H O S BR UNIT 40 22 4 2 2 MERG 2 FMAP 2 ACTA PLAN 20 BOND $H LIST 6 L.S. 10 WGHT 0.058600 0.069700 FVAR 0.96431 BR 5 0.277953 1.124488 0.393481 11.00000 0.08122 0.09769 = 0.13427 0.08215 0.04346 0.01307 S 4 0.115100 0.664057 0.684554 11.00000 0.04044 0.05648 = 0.06734 0.03510 0.01456 0.00743 O2 3 0.046547 0.477621 0.807598 11.00000 0.03194 0.06908 = 0.06845 0.03597 0.01283 0.00555 O1 3 0.660150 0.266855 0.918186 11.00000 0.04103 0.09844 = 0.11147 0.06457 0.02262 0.02396 C2 1 0.329226 0.475413 0.784184 11.00000 0.03064 0.04013 = 0.04083 0.01256 0.00691 -0.00020 C4 1 0.217497 0.328659 0.912023 11.00000 0.03879 0.04027 = 0.04030 0.01210 0.00748 -0.00158 C14 1 0.307872 0.574072 0.710574 11.00000 0.03486 0.03939 = 0.04829 0.01385 0.00934 -0.00041 C3 1 0.187762 0.432306 0.833370 11.00000 0.03289 0.04039 = 0.04292 0.01368 0.00774 -0.00058 C9 1 0.377416 0.272111 0.941019 11.00000 0.03959 0.04106 = 0.04155 0.01281 0.00664 0.00110 C1 1 0.488834 0.414521 0.810756 11.00000 0.03230 0.04174 = 0.04542 0.01107 0.00858 0.00112 C13 1 0.443056 0.602951 0.659517 11.00000 0.04464 0.05337 = 0.05924 0.02587 0.01902 0.00203 AFIX 43 H13 2 0.428773 0.664630 0.607442 11.00000 -1.20000 AFIX 0 C10 1 0.519806 0.314598 0.892059 11.00000 0.03705 0.04828 = 0.05207 0.01622 0.00977 0.00513 C5 1 0.085025 0.286385 0.958605 11.00000 0.04256 0.05722 = 0.05425 0.02235 0.01506 -0.00011 AFIX 43 H5 2 -0.021257 0.324439 0.941401 11.00000 -1.20000 AFIX 0 C15 1 0.166866 0.790007 0.604091 11.00000 0.04310 0.04385 = 0.05243 0.02052 0.00941 0.00168 C8 1 0.401494 0.175522 1.014428 11.00000 0.05506 0.05171 = 0.05304 0.02155 0.01095 0.00937 AFIX 43 H8 2 0.508317 0.139524 1.034662 11.00000 -1.20000 AFIX 0 C11 1 0.621254 0.449654 0.762241 11.00000 0.03622 0.05297 = 0.06564 0.01905 0.01915 0.00611 AFIX 43 H11 2 0.726878 0.411300 0.781636 11.00000 -1.20000 AFIX 0 C6 1 0.110789 0.188667 1.029880 11.00000 0.06415 0.06697 = 0.06452 0.03058 0.02616 -0.00113 AFIX 43 H6 2 0.021176 0.160118 1.059713 11.00000 -1.20000 AFIX 0 C17 1 0.154783 0.849770 0.413051 11.00000 0.06818 0.06232 = 0.04842 0.02309 0.01047 0.00532 AFIX 43 H17 2 0.123899 0.822768 0.326572 11.00000 -1.20000 AFIX 0 C16 1 0.122387 0.749766 0.475574 11.00000 0.05798 0.04724 = 0.05424 0.01672 0.00451 -0.00092 AFIX 43 H16 2 0.070381 0.654862 0.430995 11.00000 -1.20000 AFIX 0 C7 1 0.268400 0.132324 1.057736 11.00000 0.07613 0.06072 = 0.06069 0.03521 0.01809 0.00919 AFIX 43 H7 2 0.284472 0.065597 1.105472 11.00000 -1.20000 AFIX 0 C12 1 0.597518 0.540716 0.685730 11.00000 0.04194 0.06324 = 0.07487 0.02949 0.02762 0.00429 AFIX 43 H12 2 0.685997 0.560890 0.651096 11.00000 -1.20000 AFIX 0 C20 1 0.242064 0.930923 0.668654 11.00000 0.08075 0.05264 = 0.05023 0.01477 0.00407 -0.00898 AFIX 43 H20 2 0.270304 0.959580 0.755204 11.00000 -1.20000 AFIX 0 C18 1 0.232310 0.988361 0.478751 11.00000 0.04538 0.05528 = 0.07344 0.03678 0.01950 0.00832 C19 1 0.275994 1.030068 0.606469 11.00000 0.08151 0.04401 = 0.07659 0.01776 0.00890 -0.01014 AFIX 43 H19 2 0.328301 1.124960 0.650718 11.00000 -1.20000 AFIX 0 HKLF 4 REM c3265-2-r_a.res in P-1 REM R1 = 0.0510 for 3064 Fo > 4sig(Fo) and 0.1078 for all 5790 data REM 217 parameters refined using 0 restraints END WGHT 0.0574 0.0752 REM Highest difference peak 0.442, deepest hole -0.545, 1-sigma level 0.062 Q1 1 0.2969 1.1551 0.4849 11.00000 0.05 0.44 Q2 1 0.4442 0.2947 0.9175 11.00000 0.05 0.38 Q3 1 0.3293 1.0333 0.3617 11.00000 0.05 0.37 Q4 1 0.2749 0.4547 0.8142 11.00000 0.05 0.34 Q5 1 0.3899 0.4582 0.7983 11.00000 0.05 0.30 Q6 1 0.2743 1.0353 0.4254 11.00000 0.05 0.29 Q7 1 0.2126 0.3973 0.8911 11.00000 0.05 0.26 Q8 1 0.3724 0.5836 0.6898 11.00000 0.05 0.26 Q9 1 0.1368 0.7512 0.6468 11.00000 0.05 0.26 Q10 1 0.1956 0.1751 1.0532 11.00000 0.05 0.25 Q11 1 0.2433 0.5923 0.6881 11.00000 0.05 0.25 Q12 1 0.5474 0.4178 0.7806 11.00000 0.05 0.25 Q13 1 0.5938 0.4778 0.7072 11.00000 0.05 0.24 Q14 1 0.0687 0.8780 0.6091 11.00000 0.05 0.24 Q15 1 0.6538 0.3155 0.9362 11.00000 0.05 0.23 Q16 1 0.3154 0.2806 0.9242 11.00000 0.05 0.23 Q17 1 0.4459 0.1814 1.0313 11.00000 0.05 0.23 Q18 1 0.1825 0.9959 0.4736 11.00000 0.05 0.23 Q19 1 0.1596 0.3170 0.9515 11.00000 0.05 0.22 Q20 1 0.1141 0.8218 0.4521 11.00000 0.05 0.22 ; _shelx_res_checksum 55167 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 _atom_site_refinement_flags_adp Br Br 0.27795(5) 1.12449(5) 0.39348(5) 0.0912(2) Uani 1 1 d . . S S 0.11510(8) 0.66406(9) 0.68455(7) 0.0508(2) Uani 1 1 d . . O2 O 0.0465(2) 0.4776(2) 0.8076(2) 0.0529(5) Uani 1 1 d . . O1 O 0.6602(3) 0.2669(3) 0.9182(3) 0.0756(7) Uani 1 1 d . . C2 C 0.3292(3) 0.4754(3) 0.7842(2) 0.0372(5) Uani 1 1 d . . C4 C 0.2175(3) 0.3287(3) 0.9120(2) 0.0400(5) Uani 1 1 d . . C14 C 0.3079(3) 0.5741(3) 0.7106(2) 0.0406(5) Uani 1 1 d . . C3 C 0.1878(3) 0.4323(3) 0.8334(2) 0.0386(5) Uani 1 1 d . . C9 C 0.3774(3) 0.2721(3) 0.9410(2) 0.0410(5) Uani 1 1 d . . C1 C 0.4888(3) 0.4145(3) 0.8108(2) 0.0402(5) Uani 1 1 d . . C13 C 0.4431(3) 0.6030(3) 0.6595(3) 0.0493(6) Uani 1 1 d . . H13 H 0.4288 0.6646 0.6074 0.059 Uiso 1 1 calc R U C10 C 0.5198(3) 0.3146(3) 0.8921(3) 0.0455(6) Uani 1 1 d . . C5 C 0.0850(4) 0.2864(3) 0.9586(3) 0.0494(6) Uani 1 1 d . . H5 H -0.0213 0.3244 0.9414 0.059 Uiso 1 1 calc R U C15 C 0.1669(3) 0.7900(3) 0.6041(3) 0.0453(6) Uani 1 1 d . . C8 C 0.4015(4) 0.1755(3) 1.0144(3) 0.0521(7) Uani 1 1 d . . H8 H 0.5083 0.1395 1.0347 0.063 Uiso 1 1 calc R U C11 C 0.6213(3) 0.4497(3) 0.7622(3) 0.0500(7) Uani 1 1 d . . H11 H 0.7269 0.4113 0.7816 0.060 Uiso 1 1 calc R U C6 C 0.1108(4) 0.1887(4) 1.0299(3) 0.0610(8) Uani 1 1 d . . H6 H 0.0212 0.1601 1.0597 0.073 Uiso 1 1 calc R U C17 C 0.1548(4) 0.8498(4) 0.4131(3) 0.0586(8) Uani 1 1 d . . H17 H 0.1239 0.8228 0.3266 0.070 Uiso 1 1 calc R U C16 C 0.1224(4) 0.7498(4) 0.4756(3) 0.0541(7) Uani 1 1 d . . H16 H 0.0704 0.6549 0.4310 0.065 Uiso 1 1 calc R U C7 C 0.2684(4) 0.1323(4) 1.0577(3) 0.0618(8) Uani 1 1 d . . H7 H 0.2845 0.0656 1.1055 0.074 Uiso 1 1 calc R U C12 C 0.5975(4) 0.5407(4) 0.6857(3) 0.0557(7) Uani 1 1 d . . H12 H 0.6860 0.5609 0.6511 0.067 Uiso 1 1 calc R U C20 C 0.2421(5) 0.9309(4) 0.6687(3) 0.0631(8) Uani 1 1 d . . H20 H 0.2703 0.9596 0.7552 0.076 Uiso 1 1 calc R U C18 C 0.2323(4) 0.9884(4) 0.4788(3) 0.0533(7) Uani 1 1 d . . C19 C 0.2760(5) 1.0301(4) 0.6065(4) 0.0689(9) Uani 1 1 d . . H19 H 0.3283 1.1250 0.6507 0.083 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 Br 0.0812(3) 0.0977(4) 0.1343(4) 0.0821(3) 0.0435(3) 0.0131(2) S 0.0404(3) 0.0565(4) 0.0673(5) 0.0351(4) 0.0146(3) 0.0074(3) O2 0.0319(9) 0.0691(14) 0.0685(13) 0.0360(11) 0.0128(9) 0.0055(8) O1 0.0410(11) 0.0984(19) 0.111(2) 0.0646(16) 0.0226(12) 0.0240(11) C2 0.0306(11) 0.0401(13) 0.0408(13) 0.0126(11) 0.0069(10) -0.0002(9) C4 0.0388(12) 0.0403(14) 0.0403(13) 0.0121(11) 0.0075(10) -0.0016(10) C14 0.0349(11) 0.0394(14) 0.0483(15) 0.0139(11) 0.0093(11) -0.0004(10) C3 0.0329(11) 0.0404(13) 0.0429(14) 0.0137(11) 0.0077(10) -0.0006(9) C9 0.0396(12) 0.0411(14) 0.0416(14) 0.0128(11) 0.0066(11) 0.0011(10) C1 0.0323(11) 0.0417(14) 0.0454(14) 0.0111(11) 0.0086(10) 0.0011(10) C13 0.0446(14) 0.0534(17) 0.0592(17) 0.0259(14) 0.0190(13) 0.0020(12) C10 0.0371(12) 0.0483(16) 0.0521(16) 0.0162(13) 0.0098(11) 0.0051(11) C5 0.0426(14) 0.0572(17) 0.0542(17) 0.0223(14) 0.0151(12) -0.0001(12) C15 0.0431(13) 0.0439(15) 0.0524(16) 0.0205(13) 0.0094(12) 0.0017(11) C8 0.0551(16) 0.0517(17) 0.0530(17) 0.0216(14) 0.0109(14) 0.0094(13) C11 0.0362(13) 0.0530(17) 0.0656(19) 0.0190(14) 0.0191(13) 0.0061(12) C6 0.0642(18) 0.067(2) 0.065(2) 0.0306(17) 0.0262(16) -0.0011(16) C17 0.0682(19) 0.062(2) 0.0484(17) 0.0231(15) 0.0105(15) 0.0053(16) C16 0.0580(17) 0.0472(17) 0.0542(18) 0.0167(13) 0.0045(14) -0.0009(13) C7 0.076(2) 0.061(2) 0.0607(19) 0.0352(16) 0.0181(16) 0.0092(16) C12 0.0419(14) 0.0632(19) 0.075(2) 0.0295(16) 0.0276(14) 0.0043(13) C20 0.081(2) 0.0526(19) 0.0502(18) 0.0148(14) 0.0041(16) -0.0090(16) C18 0.0454(14) 0.0553(18) 0.073(2) 0.0368(16) 0.0195(14) 0.0083(13) C19 0.082(2) 0.0440(18) 0.077(2) 0.0178(17) 0.0089(19) -0.0101(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Br Br -0.2901 2.4595 '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 C14 S C15 101.88(12) C14 C2 C1 119.4(2) C14 C2 C3 121.3(2) C1 C2 C3 119.3(2) C5 C4 C9 118.9(2) C5 C4 C3 119.9(2) C9 C4 C3 121.2(2) C2 C14 C13 118.8(2) C2 C14 S 120.87(18) C13 C14 S 120.4(2) O2 C3 C2 120.9(2) O2 C3 C4 119.9(2) C2 C3 C4 119.2(2) C8 C9 C4 120.0(2) C8 C9 C10 120.1(2) C4 C9 C10 119.9(2) C11 C1 C2 120.2(2) C11 C1 C10 118.4(2) C2 C1 C10 121.4(2) C12 C13 C14 120.7(3) C12 C13 H13 119.6 C14 C13 H13 119.6 O1 C10 C9 120.2(3) O1 C10 C1 120.9(2) C9 C10 C1 118.9(2) C6 C5 C4 120.2(3) C6 C5 H5 119.9 C4 C5 H5 119.9 C20 C15 C16 119.2(3) C20 C15 S 120.6(2) C16 C15 S 120.1(2) C7 C8 C9 120.5(3) C7 C8 H8 119.8 C9 C8 H8 119.8 C12 C11 C1 120.3(2) C12 C11 H11 119.9 C1 C11 H11 119.9 C5 C6 C7 120.7(3) C5 C6 H6 119.6 C7 C6 H6 119.6 C18 C17 C16 119.6(3) C18 C17 H17 120.2 C16 C17 H17 120.2 C17 C16 C15 120.3(3) C17 C16 H16 119.8 C15 C16 H16 119.8 C8 C7 C6 119.6(3) C8 C7 H7 120.2 C6 C7 H7 120.2 C11 C12 C13 120.6(3) C11 C12 H12 119.7 C13 C12 H12 119.7 C15 C20 C19 120.6(3) C15 C20 H20 119.7 C19 C20 H20 119.7 C17 C18 C19 120.6(3) C17 C18 Br 119.7(2) C19 C18 Br 119.7(3) C18 C19 C20 119.7(3) C18 C19 H19 120.2 C20 C19 H19 120.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br C18 1.884(3) S C14 1.775(3) S C15 1.782(3) O2 C3 1.219(3) O1 C10 1.223(3) C2 C14 1.401(3) C2 C1 1.414(3) C2 C3 1.476(3) C4 C5 1.393(3) C4 C9 1.401(3) C4 C3 1.484(3) C14 C13 1.401(3) C9 C8 1.384(4) C9 C10 1.479(4) C1 C11 1.382(4) C1 C10 1.480(4) C13 C12 1.383(4) C13 H13 0.9300 C5 C6 1.374(4) C5 H5 0.9300 C15 C20 1.372(4) C15 C16 1.382(4) C8 C7 1.377(4) C8 H8 0.9300 C11 C12 1.370(4) C11 H11 0.9300 C6 C7 1.382(5) C6 H6 0.9300 C17 C18 1.364(5) C17 C16 1.380(4) C17 H17 0.9300 C16 H16 0.9300 C7 H7 0.9300 C12 H12 0.9300 C20 C19 1.375(5) C20 H20 0.9300 C18 C19 1.373(5) C19 H19 0.9300