#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:13:09 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257328 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557973.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_1557973 loop_ _publ_author_name 'Singh, Bara' 'Bankar, Siddheshwar K.' 'Kumar, Ketan' 'Ramasastry, S. S. V.' _publ_section_title ; Palladium-catalysed 5-endo-trig allylic (hetero)arylation ; _journal_issue 19 _journal_name_full 'Chemical Science' _journal_page_first 4948 _journal_page_last 4953 _journal_paper_doi 10.1039/D0SC01932A _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C18 H20 S' _chemical_formula_sum 'C18 H20 S' _chemical_formula_weight 268.40 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-11-11 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-11-13 deposited with the CCDC. 2020-04-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.646(12) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.0379(13) _cell_length_b 9.5393(9) _cell_length_c 16.2242(19) _cell_measurement_reflns_used 1209 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.8790 _cell_measurement_theta_min 2.8670 _cell_volume 1503.1(3) _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 0.998 _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 55.00 82.00 0.50 20.00 -- 29.89 54.00-150.00 54 2 \w 35.00 62.00 0.50 20.00 -- 29.89 54.00 150.00 54 3 \w -65.00 119.00 0.50 20.00 -- 29.89 54.00 30.00 368 ; _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 -0.0174177000 _diffrn_orient_matrix_UB_12 -0.0699828000 _diffrn_orient_matrix_UB_13 -0.0132301000 _diffrn_orient_matrix_UB_21 -0.0636976000 _diffrn_orient_matrix_UB_22 0.0071290000 _diffrn_orient_matrix_UB_23 0.0110870000 _diffrn_orient_matrix_UB_31 -0.0315146000 _diffrn_orient_matrix_UB_32 0.0238313000 _diffrn_orient_matrix_UB_33 -0.0417411000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_unetI/netI 0.0719 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 5289 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 24.996 _diffrn_reflns_theta_max 24.996 _diffrn_reflns_theta_min 2.498 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.28278 _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_density_diffrn 1.186 _exptl_crystal_F_000 576 _refine_diff_density_max 1.078 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.086 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 2636 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.094 _refine_ls_R_factor_all 0.1534 _refine_ls_R_factor_gt 0.1084 _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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2911 _refine_ls_wR_factor_ref 0.3453 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1545 _reflns_number_total 2636 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL sb08sbc_a.res in P2(1)/c sb08sbc.res created by SHELXL-2017/1 at 14:59:22 on 11-Nov-2019 REM Old TITL sb 08 sbc in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.279, Rweak 0.443, Alpha 0.037, Orientation as input REM Formula found by SHELXT: C17 N Cl CELL 0.71073 10.0379 9.5393 16.2242 90 104.646 90 ZERR 4 0.0013 0.0009 0.0019 0 0.012 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H S UNIT 72 80 4 L.S. 4 0 0 PLAN 20 BOND $H LIST 6 fmap 2 53 acta 50 OMIT -2 50 OMIT -1 0 2 OMIT -2 2 1 OMIT 2 2 1 REM REM REM WGHT 0.200000 FVAR 0.62793 S1 3 0.751508 0.809713 0.462033 11.00000 0.09203 0.05199 = 0.07574 0.00501 0.02957 0.00282 C002 1 0.761602 0.554449 0.517919 11.00000 0.05920 0.05548 = 0.05626 0.00248 0.02770 -0.00165 C003 1 0.805139 0.640363 0.592858 11.00000 0.06501 0.06327 = 0.05433 -0.00312 0.02706 0.00544 C004 1 0.731686 0.630908 0.445565 11.00000 0.06270 0.05545 = 0.06076 0.00177 0.02518 0.00211 C005 1 0.694203 0.409761 0.397203 11.00000 0.06722 0.06026 = 0.05814 -0.00015 0.02441 0.00517 C006 1 0.746426 0.402592 0.495664 11.00000 0.06911 0.05665 = 0.05362 0.00868 0.02363 0.00610 C007 1 0.803037 0.780320 0.571500 11.00000 0.06509 0.05981 = 0.06756 -0.01051 0.02836 0.00236 C008 1 0.689086 0.542634 0.371536 11.00000 0.08072 0.06114 = 0.05672 0.00446 0.02546 -0.00035 AFIX 43 H008 2 0.662513 0.573277 0.315339 11.00000 -1.20000 AFIX 0 C009 1 0.842113 0.601828 0.680212 11.00000 0.07743 0.08677 = 0.05571 -0.00629 0.02264 0.00026 AFIX 43 H009 2 0.843332 0.507847 0.695630 11.00000 -1.20000 AFIX 0 C00A 1 0.883441 0.325659 0.523411 11.00000 0.07995 0.06939 = 0.08824 0.00747 0.02773 0.02235 AFIX 137 H00A 2 0.950587 0.371956 0.500081 11.00000 -1.50000 H00B 2 0.872112 0.230744 0.503177 11.00000 -1.50000 H00C 2 0.913987 0.325784 0.584465 11.00000 -1.50000 AFIX 0 C00B 1 0.652299 0.279729 0.344864 11.00000 0.09072 0.06426 = 0.07448 -0.01170 0.03548 -0.00733 C00C 1 0.839039 0.882925 0.636013 11.00000 0.08434 0.06675 = 0.09883 -0.02214 0.03542 -0.00361 AFIX 43 H00D 2 0.837959 0.977376 0.621656 11.00000 -1.20000 AFIX 0 C00D 1 0.637796 0.327961 0.532716 11.00000 0.08604 0.08055 = 0.09241 0.02130 0.03337 -0.00838 AFIX 23 H00E 2 0.555539 0.385011 0.524835 11.00000 -1.20000 H00F 2 0.674121 0.310281 0.593113 11.00000 -1.20000 AFIX 0 C00E 1 0.875679 0.702261 0.741199 11.00000 0.08925 0.11067 = 0.06386 -0.00866 0.03046 0.00600 AFIX 43 H00G 2 0.899069 0.675785 0.798220 11.00000 -1.20000 AFIX 0 C00F 1 0.875990 0.842507 0.720789 11.00000 0.09186 0.10016 = 0.07346 -0.02762 0.02569 -0.00596 AFIX 43 H00H 2 0.900808 0.909483 0.763585 11.00000 -1.20000 AFIX 0 C00G 1 0.546165 0.199056 0.378660 11.00000 0.08954 0.07679 = 0.11590 -0.00146 0.04522 -0.00647 AFIX 23 H00I 2 0.530900 0.107384 0.352068 11.00000 -1.20000 H00J 2 0.459330 0.249295 0.365396 11.00000 -1.20000 AFIX 0 C00H 1 0.774601 0.184713 0.347040 11.00000 0.14089 0.06516 = 0.22986 -0.01067 0.11124 0.00712 AFIX 137 H00K 2 0.834797 0.228962 0.317394 11.00000 -1.50000 H00L 2 0.742611 0.097195 0.319977 11.00000 -1.50000 H00M 2 0.823679 0.167942 0.405125 11.00000 -1.50000 AFIX 0 C00I 1 0.585064 0.320668 0.252367 11.00000 0.20272 0.11668 = 0.06525 -0.02201 0.03348 -0.05259 AFIX 137 H00N 2 0.513871 0.388425 0.251127 11.00000 -1.50000 H00O 2 0.545919 0.238917 0.220911 11.00000 -1.50000 H00P 2 0.653278 0.360310 0.227113 11.00000 -1.50000 AFIX 0 C00J 1 0.603332 0.182223 0.481058 11.00000 0.14131 0.09848 = 0.17452 0.00787 0.09437 -0.01554 AFIX 23 H00Q 2 0.535231 0.131797 0.502555 11.00000 -1.20000 H00R 2 0.686222 0.125538 0.492691 11.00000 -1.20000 AFIX 0 HKLF 4 REM sb08sbc_a.res in P2(1)/c REM R1 = 0.1084 for 1545 Fo > 4sig(Fo) and 0.1534 for all 2636 data REM 175 parameters refined using 0 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 1.078, deepest hole -0.505, 1-sigma level 0.086 Q1 1 0.8464 0.1754 0.4767 11.00000 0.05 1.08 Q2 1 0.7180 0.6972 0.4404 11.00000 0.05 0.40 Q3 1 0.6843 0.7113 0.4202 11.00000 0.05 0.34 Q4 1 0.8199 0.8020 0.5973 11.00000 0.05 0.33 Q5 1 0.7436 0.9223 0.4590 11.00000 0.05 0.25 Q6 1 0.8592 0.8043 0.7228 11.00000 0.05 0.24 Q7 1 0.7206 0.3174 0.2587 11.00000 0.05 0.23 Q8 1 0.7753 0.1179 0.3457 11.00000 0.05 0.23 Q9 1 0.6205 0.3589 0.2336 11.00000 0.05 0.21 Q10 1 0.4397 0.2661 0.3394 11.00000 0.05 0.20 Q11 1 0.9220 0.3676 0.5350 11.00000 0.05 0.20 Q12 1 0.8163 0.4103 0.6656 11.00000 0.05 0.19 Q13 1 0.8082 0.9615 0.6169 11.00000 0.05 0.19 Q14 1 0.7816 0.0405 0.5149 11.00000 0.05 0.19 Q15 1 0.9432 0.4003 0.5512 11.00000 0.05 0.18 Q16 1 0.7600 0.2210 0.3238 11.00000 0.05 0.18 Q17 1 0.6812 0.9026 0.4196 11.00000 0.05 0.18 Q18 1 0.8420 0.8817 0.5062 11.00000 0.05 0.18 Q19 1 0.5016 0.3486 0.4805 11.00000 0.05 0.17 Q20 1 0.6938 0.0816 0.2826 11.00000 0.05 0.17 REM The information below was added by Olex2. REM REM R1 = 0.1084 for 1545 Fo > 4sig(Fo) and 0.1534 for all 8774 data REM n/a parameters refined using n/a restraints REM Highest difference peak 1.08, deepest hole -0.50 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1534 REM R1_gt = 0.1084 REM wR_ref = 0.3453 REM GOOF = 1.094 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 8774 REM Reflections_gt = 1545 REM Parameters = n/a REM Hole = -0.50 REM Peak = 1.08 REM Flack = n/a ; _cod_data_source_file d0sc01932a2.cif _cod_data_source_block sb08sbc _cod_depositor_comments ;Adding full bibliography for 1557972--1557973.cif. Adding full bibliography for 1557972--1557973.cif. ; _cod_database_code 1557973 _shelx_shelxl_version_number 2017/1 _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 99.82 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 24.97 _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 Secondary CH2 refined with riding coordinates: C00D(H00E,H00F), C00G(H00I,H00J), C00J(H00Q,H00R) 2.b Aromatic/amide H refined with riding coordinates: C008(H008), C009(H009), C00C(H00D), C00E(H00G), C00F(H00H) 2.c Idealised Me refined as rotating group: C00A(H00A,H00B,H00C), C00H(H00K,H00L,H00M), C00I(H00N,H00O,H00P) ; _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 2.440 _oxdiff_exptl_absorpt_empirical_full_min 0.539 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.75151(15) 0.80971(15) 0.46203(8) 0.0717(6) Uani 1 1 d . . . . . C002 C 0.7616(4) 0.5544(5) 0.5179(3) 0.0546(12) Uani 1 1 d . . . . . C003 C 0.8051(5) 0.6404(5) 0.5929(3) 0.0587(12) Uani 1 1 d . . . . . C004 C 0.7317(5) 0.6309(5) 0.4456(3) 0.0579(12) Uani 1 1 d . . . . . C005 C 0.6942(5) 0.4098(5) 0.3972(3) 0.0603(12) Uani 1 1 d . . . . . C006 C 0.7464(5) 0.4026(5) 0.4957(3) 0.0583(12) Uani 1 1 d . . . . . C007 C 0.8030(5) 0.7803(5) 0.5715(3) 0.0621(13) Uani 1 1 d . . . . . C008 C 0.6891(5) 0.5426(5) 0.3715(3) 0.0647(13) Uani 1 1 d . . . . . H008 H 0.662513 0.573277 0.315339 0.078 Uiso 1 1 calc R . . . . C009 C 0.8421(5) 0.6018(7) 0.6802(3) 0.0723(14) Uani 1 1 d . . . . . H009 H 0.843332 0.507847 0.695630 0.087 Uiso 1 1 calc R . . . . C00A C 0.8834(6) 0.3257(6) 0.5234(4) 0.0780(16) Uani 1 1 d . . . . . H00A H 0.950587 0.371956 0.500081 0.117 Uiso 1 1 calc GR . . . . H00B H 0.872112 0.230744 0.503177 0.117 Uiso 1 1 calc GR . . . . H00C H 0.913987 0.325784 0.584465 0.117 Uiso 1 1 calc GR . . . . C00B C 0.6523(6) 0.2797(6) 0.3449(3) 0.0739(15) Uani 1 1 d . . . . . C00C C 0.8390(6) 0.8829(6) 0.6360(4) 0.0811(17) Uani 1 1 d . . . . . H00D H 0.837959 0.977376 0.621656 0.097 Uiso 1 1 calc R . . . . C00D C 0.6378(6) 0.3280(6) 0.5327(4) 0.0844(17) Uani 1 1 d . . . . . H00E H 0.555539 0.385011 0.524835 0.101 Uiso 1 1 calc R . . . . H00F H 0.674121 0.310281 0.593113 0.101 Uiso 1 1 calc R . . . . C00E C 0.8757(6) 0.7023(8) 0.7412(3) 0.0859(18) Uani 1 1 d . . . . . H00G H 0.899069 0.675785 0.798220 0.103 Uiso 1 1 calc R . . . . C00F C 0.8760(6) 0.8425(8) 0.7208(4) 0.0876(18) Uani 1 1 d . . . . . H00H H 0.900808 0.909483 0.763585 0.105 Uiso 1 1 calc R . . . . C00G C 0.5462(6) 0.1991(7) 0.3787(4) 0.0906(18) Uani 1 1 d . . . . . H00I H 0.530900 0.107384 0.352068 0.109 Uiso 1 1 calc R . . . . H00J H 0.459330 0.249295 0.365396 0.109 Uiso 1 1 calc R . . . . C00H C 0.7746(8) 0.1847(7) 0.3470(6) 0.134(3) Uani 1 1 d . . . . . H00K H 0.834797 0.228962 0.317394 0.201 Uiso 1 1 calc GR . . . . H00L H 0.742611 0.097195 0.319977 0.201 Uiso 1 1 calc GR . . . . H00M H 0.823679 0.167942 0.405125 0.201 Uiso 1 1 calc GR . . . . C00I C 0.5851(10) 0.3207(8) 0.2524(4) 0.128(3) Uani 1 1 d . . . . . H00N H 0.513871 0.388425 0.251127 0.192 Uiso 1 1 calc GR . . . . H00O H 0.545919 0.238917 0.220911 0.192 Uiso 1 1 calc GR . . . . H00P H 0.653278 0.360310 0.227113 0.192 Uiso 1 1 calc GR . . . . C00J C 0.6033(9) 0.1822(8) 0.4811(6) 0.128(3) Uani 1 1 d . . . . . H00Q H 0.535231 0.131797 0.502555 0.154 Uiso 1 1 calc R . . . . H00R H 0.686222 0.125538 0.492691 0.154 Uiso 1 1 calc R . . . . 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 S1 0.0920(12) 0.0520(10) 0.0757(10) 0.0050(5) 0.0296(8) 0.0028(6) C002 0.059(3) 0.055(3) 0.056(2) 0.0025(19) 0.028(2) -0.002(2) C003 0.065(3) 0.063(3) 0.054(2) -0.0031(19) 0.027(2) 0.005(2) C004 0.063(3) 0.055(3) 0.061(3) 0.002(2) 0.025(2) 0.002(2) C005 0.067(3) 0.060(3) 0.058(3) 0.000(2) 0.024(2) 0.005(2) C006 0.069(3) 0.057(3) 0.054(2) 0.009(2) 0.024(2) 0.006(2) C007 0.065(3) 0.060(3) 0.068(3) -0.011(2) 0.028(2) 0.002(2) C008 0.081(3) 0.061(3) 0.057(3) 0.004(2) 0.025(2) 0.000(3) C009 0.077(3) 0.087(4) 0.056(3) -0.006(2) 0.023(2) 0.000(3) C00A 0.080(4) 0.069(4) 0.088(4) 0.007(3) 0.028(3) 0.022(3) C00B 0.091(4) 0.064(3) 0.074(3) -0.012(2) 0.035(3) -0.007(3) C00C 0.084(4) 0.067(4) 0.099(4) -0.022(3) 0.035(3) -0.004(3) C00D 0.086(4) 0.081(4) 0.092(4) 0.021(3) 0.033(3) -0.008(3) C00E 0.089(4) 0.111(5) 0.064(3) -0.009(3) 0.030(3) 0.006(3) C00F 0.092(4) 0.100(5) 0.073(4) -0.028(3) 0.026(3) -0.006(4) C00G 0.090(4) 0.077(4) 0.116(5) -0.001(3) 0.045(4) -0.006(3) C00H 0.141(6) 0.065(5) 0.230(10) -0.011(5) 0.111(7) 0.007(4) C00I 0.203(9) 0.117(6) 0.065(4) -0.022(3) 0.033(4) -0.053(6) C00J 0.141(7) 0.098(6) 0.175(8) 0.008(5) 0.094(6) -0.016(5) 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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C004 S1 C007 89.5(2) . . ? C003 C002 C006 138.4(4) . . ? C004 C002 C003 112.3(5) . . ? C004 C002 C006 109.1(4) . . ? C007 C003 C002 110.9(4) . . ? C007 C003 C009 119.0(5) . . ? C009 C003 C002 130.0(5) . . ? C002 C004 S1 114.0(4) . . ? C002 C004 C008 111.3(5) . . ? C008 C004 S1 134.7(4) . . ? C008 C005 C006 109.9(4) . . ? C008 C005 C00B 128.8(4) . . ? C00B C005 C006 121.3(4) . . ? C002 C006 C005 101.2(4) . . ? C002 C006 C00A 111.5(4) . . ? C002 C006 C00D 113.1(4) . . ? C00A C006 C005 111.7(4) . . ? C00A C006 C00D 109.6(4) . . ? C00D C006 C005 109.4(4) . . ? C003 C007 S1 113.2(3) . . ? C003 C007 C00C 120.0(5) . . ? C00C C007 S1 126.8(4) . . ? C004 C008 H008 125.8 . . ? C005 C008 C004 108.4(4) . . ? C005 C008 H008 125.8 . . ? C003 C009 H009 120.0 . . ? C00E C009 C003 119.9(6) . . ? C00E C009 H009 120.0 . . ? C006 C00A H00A 109.5 . . ? C006 C00A H00B 109.5 . . ? C006 C00A H00C 109.5 . . ? H00A C00A H00B 109.5 . . ? H00A C00A H00C 109.5 . . ? H00B C00A H00C 109.5 . . ? C005 C00B C00G 109.6(4) . . ? C005 C00B C00H 111.7(5) . . ? C005 C00B C00I 109.5(5) . . ? C00G C00B C00I 107.8(5) . . ? C00H C00B C00G 108.9(5) . . ? C00H C00B C00I 109.2(6) . . ? C007 C00C H00D 120.1 . . ? C00F C00C C007 119.8(6) . . ? C00F C00C H00D 120.1 . . ? C006 C00D H00E 110.6 . . ? C006 C00D H00F 110.6 . . ? C006 C00D C00J 105.9(5) . . ? H00E C00D H00F 108.7 . . ? C00J C00D H00E 110.6 . . ? C00J C00D H00F 110.6 . . ? C009 C00E H00G 119.2 . . ? C009 C00E C00F 121.7(5) . . ? C00F C00E H00G 119.2 . . ? C00C C00F H00H 120.3 . . ? C00E C00F C00C 119.5(5) . . ? C00E C00F H00H 120.3 . . ? C00B C00G H00I 110.0 . . ? C00B C00G H00J 110.0 . . ? C00B C00G C00J 108.7(5) . . ? H00I C00G H00J 108.3 . . ? C00J C00G H00I 110.0 . . ? C00J C00G H00J 110.0 . . ? C00B C00H H00K 109.5 . . ? C00B C00H H00L 109.5 . . ? C00B C00H H00M 109.5 . . ? H00K C00H H00L 109.5 . . ? H00K C00H H00M 109.5 . . ? H00L C00H H00M 109.5 . . ? C00B C00I H00N 109.5 . . ? C00B C00I H00O 109.5 . . ? C00B C00I H00P 109.5 . . ? H00N C00I H00O 109.5 . . ? H00N C00I H00P 109.5 . . ? H00O C00I H00P 109.5 . . ? C00D C00J C00G 114.8(6) . . ? C00D C00J H00Q 108.6 . . ? C00D C00J H00R 108.6 . . ? C00G C00J H00Q 108.6 . . ? C00G C00J H00R 108.6 . . ? H00Q C00J H00R 107.5 . . ? 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 S1 C004 1.730(5) . ? S1 C007 1.742(5) . ? C002 C003 1.440(6) . ? C002 C004 1.350(6) . ? C002 C006 1.491(7) . ? C003 C007 1.378(7) . ? C003 C009 1.420(6) . ? C004 C008 1.440(6) . ? C005 C006 1.552(6) . ? C005 C008 1.331(7) . ? C005 C00B 1.502(7) . ? C006 C00A 1.523(7) . ? C006 C00D 1.546(7) . ? C007 C00C 1.412(7) . ? C008 H008 0.9300 . ? C009 H009 0.9300 . ? C009 C00E 1.357(8) . ? C00A H00A 0.9600 . ? C00A H00B 0.9600 . ? C00A H00C 0.9600 . ? C00B C00G 1.524(8) . ? C00B C00H 1.519(9) . ? C00B C00I 1.532(8) . ? C00C H00D 0.9300 . ? C00C C00F 1.386(8) . ? C00D H00E 0.9700 . ? C00D H00F 0.9700 . ? C00D C00J 1.615(10) . ? C00E H00G 0.9300 . ? C00E C00F 1.378(9) . ? C00F H00H 0.9300 . ? C00G H00I 0.9700 . ? C00G H00J 0.9700 . ? C00G C00J 1.623(10) . ? C00H H00K 0.9600 . ? C00H H00L 0.9600 . ? C00H H00M 0.9600 . ? C00I H00N 0.9600 . ? C00I H00O 0.9600 . ? C00I H00P 0.9600 . ? C00J H00Q 0.9700 . ? C00J H00R 0.9700 . ?