# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name _publ_author_address 'M. Chavarot' ; UMR 7611 - Chimie Organique Tour 44-45 - 1er etage Case 181 4, place Jussieu F-75252 PARIS Cedex 5 ; 'M. Rivard' ; UMR 7611 - Chimie Organique Tour 44-45 - 1er etage Case 181 4, place Jussieu F-75252 PARIS Cedex 5 ; 'F. Rose-Munch' ; UMR 7611 - Chimie Organique Tour 44-45 - 1er etage Case 181 4, place Jussieu F-75252 PARIS Cedex 5 ; 'E.Rose ' ; UMR 7611 - Chimie Organique Tour 44-45 - 1er etage Case 181 4, place Jussieu F-75252 PARIS Cedex 5 ; S.Py ; UMR 7611 - Chimie Organique Tour 44-45 - 1er etage Case 181 4, place Jussieu F-75252 PARIS Cedex 5 ; _publ_contact_author_address ; UMR 7611 - Chimie Organique Tour 44-45 - 1er etage Case 181 4, place Jussieu F-75252 PARIS Cedex 5 ; _publ_contact_author_email chavarot@ccr.jussieu.fr _publ_contact_author_fax '(33)1 44 27 55 04' _publ_contact_author_phone '(33)1 44 27 34 44' _publ_contact_author_name 'M. Chavarot' _publ_requested_category CO # choose from: FI FM FO CI CM CO AD# _publ_requested_coeditor_name ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; First asymmetric SmI2-induced cross-coupling of Cr(CO)3-complexed nitrones with carbonyl compounds ; data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 233610' _audit_creation_date 04-11-03 _audit_creation_method CRYSTALS_ver_12-03-99 _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment mixed #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 9.2513(18) _cell_angle_alpha 110.720(13) _cell_length_b 9.7274(12) _cell_angle_beta 101.703(19) _cell_length_c 13.164(3) _cell_angle_gamma 100.932(11) _cell_volume 1039.9(4) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'Cr ' 0.3209 0.6236 10.6406 6.1038 7.3537 0.3920 3.3240 20.2626 1.4922 98.7399 1.1832 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C21 H23 Cr1 N1 O6 ' _chemical_formula_moiety ' C21 H23 Cr1 N1 O6 ' _chemical_compound_source ; ? ; _chemical_formula_weight 437.40 _cell_measurement_reflns_used 81 _cell_measurement_theta_min 4.3 _cell_measurement_theta_max 22.6 _cell_measurement_temperature 295 _exptl_crystal_description ' block ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.36 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.587 _diffrn_measurement_device_type ; Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; EvalCCD (Duisenberg & Schreurs 1990-2000) ; _computing_cell_refinement ; Dirax/lsq (Duisenberg & Schreurs, 1989-2000) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; DIFABS (Walker & Stuart, 1983) ; _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.81 # Sheldrick geometric definitions 0.94 0.94 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 295 _diffrn_reflns_number 13582 _reflns_number_total 3934 _diffrn_reflns_av_R_equivalents 0.11 # Number of reflections with Friedels Law is 3934 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4082 _diffrn_reflns_theta_min 2.270 _diffrn_reflns_theta_max 25.997 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 23.917 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _refine_diff_density_min -0.39 _refine_diff_density_max 0.25 _refine_ls_number_reflns 2617 _refine_ls_number_restraints 0 _refine_ls_number_parameters 264 #_refine_ls_R_factor_ref 0.0396 _refine_ls_wR_factor_ref 0.0453 _refine_ls_goodness_of_fit_ref 1.0710 #_reflns_number_all 3931 _refine_ls_R_factor_all 0.0695 _refine_ls_wR_factor_all 0.0658 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 2617 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_gt 0.0453 _refine_ls_shift/su_max 0.000148 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.972 0.347 0.693 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Walker, N., and Stuart, D. Acta Cryst, (1983) A39, 158-166 Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_disorder_assembly _atom_site_refinement_disorder_group _atom_site_attached_hydrogens Cr1 Cr -0.06872(5) -0.41792(5) 0.25080(4) 0.0379 1.0000 Uani . . . . . . O1 O -0.2858(2) -0.1835(2) 0.30190(15) 0.0399 1.0000 Uani . . . . . . O2 O 0.1039(2) -0.14661(19) 0.10064(14) 0.0378 1.0000 Uani . . . . . . O3 O -0.1549(3) 0.0441(2) 0.06515(17) 0.0503 1.0000 Uani . . . . . . O19 O -0.0327(4) -0.6493(4) 0.3473(3) 0.0993 1.0000 Uani . . . . . . O20 O 0.2520(3) -0.3937(3) 0.2340(3) 0.0849 1.0000 Uani . . . . . . O21 O 0.0582(3) -0.1711(3) 0.4869(2) 0.0695 1.0000 Uani . . . . . . N1 N 0.0433(2) -0.0456(2) 0.18012(16) 0.0314 1.0000 Uani . . . . . . C1 C -0.2604(3) -0.3078(3) 0.2287(2) 0.0328 1.0000 Uani . . . . . . C2 C -0.1666(3) -0.2800(3) 0.15976(19) 0.0315 1.0000 Uani . . . . . . C3 C -0.1396(3) -0.4084(3) 0.0827(2) 0.0411 1.0000 Uani . . . . . . C4 C -0.2032(4) -0.5588(3) 0.0700(3) 0.0516 1.0000 Uani . . . . . . C5 C -0.2911(4) -0.5813(3) 0.1402(3) 0.0509 1.0000 Uani . . . . . . C6 C -0.3220(3) -0.4572(3) 0.2185(2) 0.0443 1.0000 Uani . . . . . . C7 C -0.1192(3) -0.1193(3) 0.16324(19) 0.0304 1.0000 Uani . . . . . . C8 C -0.2239(3) -0.1051(3) 0.0599(2) 0.0383 1.0000 Uani . . . . . . C9 C -0.2399(4) -0.2239(4) -0.0566(2) 0.0540 1.0000 Uani . . . . . . C10 C -0.3824(4) -0.1064(4) 0.0765(3) 0.0571 1.0000 Uani . . . . . . C11 C 0.1436(3) -0.0057(3) 0.2942(2) 0.0398 1.0000 Uani . . . . . . C12 C 0.2978(3) 0.1039(3) 0.31982(19) 0.0326 1.0000 Uani . . . . . . C13 C 0.3120(3) 0.2568(3) 0.3424(2) 0.0397 1.0000 Uani . . . . . . C14 C 0.4533(4) 0.3598(3) 0.3713(2) 0.0514 1.0000 Uani . . . . . . C15 C 0.5840(4) 0.3117(4) 0.3787(3) 0.0599 1.0000 Uani . . . . . . C16 C 0.5715(4) 0.1609(5) 0.3557(3) 0.0664 1.0000 Uani . . . . . . C17 C 0.4292(4) 0.0559(4) 0.3249(3) 0.0531 1.0000 Uani . . . . . . C18 C -0.3467(4) -0.1974(4) 0.3904(3) 0.0526 1.0000 Uani . . . . . . C19 C -0.0464(4) -0.5601(4) 0.3098(3) 0.0633 1.0000 Uani . . . . . . C20 C 0.1283(4) -0.4031(4) 0.2397(3) 0.0539 1.0000 Uani . . . . . . C21 C 0.0098(3) -0.2670(4) 0.3964(3) 0.0459 1.0000 Uani . . . . . . H2 H 0.1321 -0.0922 0.0593 0.063(2) 1.0000 Uiso . . . . . . H3 H -0.0568 0.0763 0.1132 0.063(2) 1.0000 Uiso . . . . . . H31 H -0.0723 -0.3920 0.0349 0.063(2) 1.0000 Uiso . . . . . . H41 H -0.1857 -0.6479 0.0116 0.063(2) 1.0000 Uiso . . . . . . H51 H -0.3327 -0.6873 0.1347 0.063(2) 1.0000 Uiso . . . . . . H61 H -0.3878 -0.4751 0.2669 0.063(2) 1.0000 Uiso . . . . . . H71 H -0.1354 -0.0589 0.2371 0.063(2) 1.0000 Uiso . . . . . . H91 H -0.2876 -0.3285 -0.0620 0.063(2) 1.0000 Uiso . . . . . . H92 H -0.3067 -0.2034 -0.1162 0.063(2) 1.0000 Uiso . . . . . . H93 H -0.1358 -0.2183 -0.0683 0.063(2) 1.0000 Uiso . . . . . . H101 H -0.4337 -0.2088 0.0732 0.063(2) 1.0000 Uiso . . . . . . H102 H -0.3710 -0.0247 0.1520 0.063(2) 1.0000 Uiso . . . . . . H103 H -0.4465 -0.0871 0.0149 0.063(2) 1.0000 Uiso . . . . . . H111 H 0.1599 -0.1017 0.3001 0.063(2) 1.0000 Uiso . . . . . . H112 H 0.0918 0.0429 0.3513 0.063(2) 1.0000 Uiso . . . . . . H131 H 0.2176 0.2929 0.3375 0.063(2) 1.0000 Uiso . . . . . . H141 H 0.4611 0.4699 0.3871 0.063(2) 1.0000 Uiso . . . . . . H151 H 0.6872 0.3867 0.4007 0.063(2) 1.0000 Uiso . . . . . . H161 H 0.6664 0.1255 0.3610 0.063(2) 1.0000 Uiso . . . . . . H171 H 0.4218 -0.0546 0.3065 0.063(2) 1.0000 Uiso . . . . . . H181 H -0.3592 -0.0966 0.4375 0.063(2) 1.0000 Uiso . . . . . . H182 H -0.4492 -0.2768 0.3563 0.063(2) 1.0000 Uiso . . . . . . H183 H -0.2745 -0.2288 0.4396 0.063(2) 1.0000 Uiso . . . . . . 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 Cr1 0.0358(2) 0.0354(2) 0.0425(3) 0.01682(19) 0.01106(18) 0.00915(17) O1 0.0451(10) 0.0486(11) 0.0328(9) 0.0189(8) 0.0191(8) 0.0156(8) O2 0.0468(10) 0.0341(9) 0.0317(9) 0.0093(8) 0.0186(8) 0.0101(8) O3 0.0621(13) 0.0453(11) 0.0405(11) 0.0240(9) 0.0050(9) 0.0065(9) O19 0.088(2) 0.108(2) 0.168(3) 0.107(3) 0.054(2) 0.0554(18) O20 0.0459(14) 0.0896(19) 0.110(2) 0.0255(17) 0.0325(14) 0.0176(13) O21 0.0714(16) 0.0787(17) 0.0399(13) 0.0165(13) -0.0007(11) 0.0138(13) N1 0.0336(11) 0.0330(11) 0.0199(10) 0.0058(8) 0.0082(8) 0.0022(8) C1 0.0297(12) 0.0383(13) 0.0248(12) 0.0113(11) 0.0036(10) 0.0054(10) C2 0.0331(12) 0.0331(12) 0.0204(11) 0.0077(10) 0.0037(10) 0.0030(10) C3 0.0442(15) 0.0377(14) 0.0322(14) 0.0061(11) 0.0121(12) 0.0064(11) C4 0.0627(19) 0.0288(13) 0.0446(16) -0.0004(12) 0.0138(14) 0.0039(13) C5 0.0489(16) 0.0357(15) 0.0549(18) 0.0160(14) 0.0064(14) -0.0029(12) C6 0.0355(14) 0.0485(16) 0.0467(17) 0.0240(14) 0.0080(12) 0.0023(12) C7 0.0343(12) 0.0316(12) 0.0186(11) 0.0071(9) 0.0058(9) 0.0029(10) C8 0.0431(14) 0.0382(13) 0.0267(13) 0.0129(11) 0.0028(11) 0.0046(11) C9 0.0652(19) 0.0557(18) 0.0226(14) 0.0093(13) -0.0019(13) 0.0049(15) C10 0.0471(17) 0.071(2) 0.0558(19) 0.0331(17) 0.0060(14) 0.0193(15) C11 0.0402(14) 0.0456(15) 0.0211(12) 0.0109(11) 0.0015(10) -0.0018(12) C12 0.0329(13) 0.0384(13) 0.0183(11) 0.0069(10) 0.0057(10) 0.0031(10) C13 0.0442(15) 0.0416(14) 0.0294(13) 0.0094(11) 0.0125(11) 0.0118(12) C14 0.065(2) 0.0378(15) 0.0365(15) 0.0065(12) 0.0158(14) -0.0034(14) C15 0.0423(17) 0.069(2) 0.0443(18) 0.0114(16) 0.0089(14) -0.0110(15) C16 0.0361(16) 0.083(3) 0.074(2) 0.025(2) 0.0132(16) 0.0183(16) C17 0.0509(17) 0.0456(16) 0.0569(19) 0.0138(14) 0.0128(14) 0.0178(14) C18 0.0560(18) 0.073(2) 0.0427(16) 0.0282(15) 0.0286(14) 0.0252(16) C19 0.0504(18) 0.068(2) 0.094(3) 0.049(2) 0.0296(18) 0.0267(16) C20 0.0482(18) 0.0464(17) 0.062(2) 0.0166(15) 0.0165(15) 0.0118(14) C21 0.0398(15) 0.0560(18) 0.0462(18) 0.0287(16) 0.0063(13) 0.0150(13) _refine_ls_extinction_coef 41 _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cr1 . C21 . 1.843(3) yes Cr1 . C20 . 1.841(3) yes Cr1 . C19 . 1.833(3) yes Cr1 . C6 . 2.227(3) yes Cr1 . C5 . 2.188(3) yes Cr1 . C4 . 2.221(3) yes Cr1 . C3 . 2.217(3) yes Cr1 . C2 . 2.284(2) yes Cr1 . C1 . 2.261(3) yes O1 . C18 . 1.429(3) yes O1 . C1 . 1.350(3) yes O2 . H2 . 0.924 no O2 . N1 . 1.447(3) yes O3 . H3 . 0.917 no O3 . C8 . 1.442(3) yes O19 . C19 . 1.154(4) yes O20 . C20 . 1.150(4) yes O21 . C21 . 1.153(4) yes N1 . C11 . 1.467(3) yes N1 . C7 . 1.472(3) yes C1 . C6 . 1.405(4) yes C1 . C2 . 1.433(3) yes C2 . C7 . 1.522(3) yes C2 . C3 . 1.407(4) yes C3 . H31 . 1.000 no C3 . C4 . 1.405(4) yes C4 . H41 . 1.000 no C4 . C5 . 1.394(5) yes C5 . H51 . 1.001 no C5 . C6 . 1.404(5) yes C6 . H61 . 1.001 no C7 . H71 . 1.000 no C7 . C8 . 1.568(3) yes C8 . C10 . 1.524(4) yes C8 . C9 . 1.516(4) yes C9 . H93 . 1.000 no C9 . H92 . 0.999 no C9 . H91 . 1.001 no C10 . H103 . 0.999 no C10 . H102 . 0.999 no C10 . H101 . 1.001 no C11 . H112 . 1.000 no C11 . H111 . 1.000 no C11 . C12 . 1.503(3) yes C12 . C17 . 1.380(4) yes C12 . C13 . 1.384(4) yes C13 . H131 . 1.000 no C13 . C14 . 1.374(4) yes C14 . H141 . 1.001 no C14 . C15 . 1.374(5) yes C15 . H151 . 1.001 no C15 . C16 . 1.366(5) yes C16 . H161 . 1.001 no C16 . C17 . 1.386(5) yes C17 . H171 . 1.000 no C18 . H183 . 1.001 no C18 . H182 . 1.001 no C18 . H181 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C21 . Cr1 . C20 . 89.68(14) yes C21 . Cr1 . C19 . 88.62(16) yes C20 . Cr1 . C19 . 87.57(15) yes C21 . Cr1 . C6 . 102.96(12) yes C20 . Cr1 . C6 . 166.05(13) yes C19 . Cr1 . C6 . 98.47(13) yes C21 . Cr1 . C5 . 137.63(13) yes C20 . Cr1 . C5 . 131.93(14) yes C19 . Cr1 . C5 . 86.08(14) yes C6 . Cr1 . C5 . 37.08(12) yes C21 . Cr1 . C4 . 164.37(12) yes C20 . Cr1 . C4 . 100.08(14) yes C19 . Cr1 . C4 . 103.86(15) yes C6 . Cr1 . C4 . 66.32(12) yes C5 . Cr1 . C4 . 36.84(12) yes C21 . Cr1 . C3 . 132.21(11) yes C20 . Cr1 . C3 . 89.36(13) yes C19 . Cr1 . C3 . 139.04(15) yes C6 . Cr1 . C3 . 77.81(11) yes C5 . Cr1 . C3 . 66.30(11) yes C21 . Cr1 . C2 . 99.25(10) yes C20 . Cr1 . C2 . 106.22(12) yes C19 . Cr1 . C2 . 164.04(12) yes C6 . Cr1 . C2 . 66.32(9) yes C5 . Cr1 . C2 . 78.73(10) yes C21 . Cr1 . C1 . 86.84(11) yes C20 . Cr1 . C1 . 140.96(12) yes C19 . Cr1 . C1 . 131.13(12) yes C6 . Cr1 . C1 . 36.47(10) yes C5 . Cr1 . C1 . 66.19(10) yes C4 . Cr1 . C3 . 36.91(10) yes C4 . Cr1 . C2 . 66.40(10) yes C3 . Cr1 . C2 . 36.38(9) yes C4 . Cr1 . C1 . 77.87(10) yes C3 . Cr1 . C1 . 65.43(10) yes C2 . Cr1 . C1 . 36.75(9) yes C18 . O1 . C1 . 118.8(2) yes H2 . O2 . N1 . 103.495 no H3 . O3 . C8 . 105.895 no C11 . N1 . C7 . 113.45(18) yes C11 . N1 . O2 . 106.69(19) yes C7 . N1 . O2 . 110.51(17) yes C6 . C1 . C2 . 120.9(2) yes C6 . C1 . O1 . 122.9(2) yes C2 . C1 . O1 . 116.2(2) yes C6 . C1 . Cr1 . 70.47(15) yes C2 . C1 . Cr1 . 72.50(14) yes O1 . C1 . Cr1 . 130.41(16) yes C7 . C2 . C3 . 123.8(2) yes C7 . C2 . C1 . 118.8(2) yes C3 . C2 . C1 . 117.0(2) yes C7 . C2 . Cr1 . 137.35(16) yes C3 . C2 . Cr1 . 69.23(15) yes C1 . C2 . Cr1 . 70.74(13) yes H31 . C3 . C4 . 118.687 no H31 . C3 . C2 . 118.616 no C4 . C3 . C2 . 122.7(3) yes H31 . C3 . Cr1 . 127.462 no C4 . C3 . Cr1 . 71.71(17) yes C2 . C3 . Cr1 . 74.39(14) yes H41 . C4 . C5 . 120.708 no H41 . C4 . C3 . 120.500 no C5 . C4 . C3 . 118.8(3) yes H41 . C4 . Cr1 . 130.192 no C5 . C4 . Cr1 . 70.28(17) yes C3 . C4 . Cr1 . 71.38(16) yes H51 . C5 . C6 . 119.595 no H51 . C5 . C4 . 119.571 no C6 . C5 . C4 . 120.8(3) yes H51 . C5 . Cr1 . 126.434 no C6 . C5 . Cr1 . 72.97(16) yes C4 . C5 . Cr1 . 72.88(17) yes H61 . C6 . C5 . 120.165 no H61 . C6 . C1 . 120.040 no C5 . C6 . C1 . 119.8(3) yes H61 . C6 . Cr1 . 129.216 no C5 . C6 . Cr1 . 69.95(17) yes C1 . C6 . Cr1 . 73.07(15) yes H71 . C7 . C8 . 112.480 no H71 . C7 . N1 . 102.448 no C8 . C7 . N1 . 109.61(19) yes H71 . C7 . C2 . 99.842 no C8 . C7 . C2 . 111.76(19) yes N1 . C7 . C2 . 119.9(2) yes C10 . C8 . C9 . 110.1(2) yes C10 . C8 . O3 . 107.3(2) yes C9 . C8 . O3 . 108.2(2) yes C10 . C8 . C7 . 109.0(2) yes C9 . C8 . C7 . 115.9(2) yes O3 . C8 . C7 . 105.99(19) yes H93 . C9 . H92 . 109.557 no H93 . C9 . H91 . 109.422 no H92 . C9 . H91 . 109.488 no H93 . C9 . C8 . 109.461 no H92 . C9 . C8 . 109.495 no H91 . C9 . C8 . 109.404 no H103 . C10 . H102 . 109.611 no H103 . C10 . H101 . 109.424 no H102 . C10 . H101 . 109.473 no H103 . C10 . C8 . 109.459 no H102 . C10 . C8 . 109.495 no H101 . C10 . C8 . 109.365 no H112 . C11 . H111 . 109.423 no H112 . C11 . C12 . 108.734 no H111 . C11 . C12 . 108.713 no H112 . C11 . N1 . 108.728 no H111 . C11 . N1 . 108.758 no C12 . C11 . N1 . 112.4(2) yes C17 . C12 . C13 . 118.3(2) yes C17 . C12 . C11 . 121.0(3) yes C13 . C12 . C11 . 120.6(2) yes H131 . C13 . C14 . 119.415 no H131 . C13 . C12 . 119.305 no C14 . C13 . C12 . 121.3(3) yes H141 . C14 . C15 . 119.975 no H141 . C14 . C13 . 120.049 no C15 . C14 . C13 . 120.0(3) yes H151 . C15 . C16 . 120.450 no H151 . C15 . C14 . 120.187 no C16 . C15 . C14 . 119.4(3) yes H161 . C16 . C17 . 119.437 no H161 . C16 . C15 . 119.586 no C17 . C16 . C15 . 121.0(3) yes H171 . C17 . C12 . 119.986 no H171 . C17 . C16 . 119.983 no C12 . C17 . C16 . 120.0(3) yes H183 . C18 . H182 . 109.345 no H183 . C18 . H181 . 109.417 no H182 . C18 . H181 . 109.442 no H183 . C18 . O1 . 109.484 no H182 . C18 . O1 . 109.541 no H181 . C18 . O1 . 109.597 no O19 . C19 . Cr1 . 179.7(3) yes O20 . C20 . Cr1 . 179.2(3) yes O21 . C21 . Cr1 . 179.0(3) yes