#------------------------------------------------------------------------------ #$Date: 2013-12-29 13:49:26 +0200 (Sun, 29 Dec 2013) $ #$Revision: 91935 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/06/33/4063339.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_4063339 loop_ _publ_author_name 'Merle Arrowsmith' 'Michael S. Hill' 'Gabriele Kociok-K\"hon' _publ_section_title ; Dearomatization and C--H Deprotonation with Heavier Group 2 Alkyls: Does Size Matter? ; _journal_issue 19 _journal_name_full Organometallics _journal_page_first 4203 _journal_page_last 4206 _journal_volume 29 _journal_year 2010 _chemical_formula_moiety 'C41 H57 Ca N3 O2' _chemical_formula_sum 'C41 H57 Ca N3 O2' _chemical_formula_weight 663.98 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 102.483(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.5654(3) _cell_length_b 17.1777(5) _cell_length_c 19.9552(6) _cell_measurement_reflns_used 36478 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.485 _cell_measurement_theta_min 2.910 _cell_volume 3870.72(19) _computing_cell_refinement 'HKL Scalepack (Otwinski & Minor, 1997)' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_data_reduction ; DENZO-SCALEPACK Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press. ; _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _computing_structure_refinement ; SHELXL97 -Program for Crystal Structure Analysis (Release 97-2). Sheldrick, G.M., Instit\"ut f\"ur Anorganische Chemie der Universit\"at, Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998 ; _computing_structure_solution ; SIR2004- Version 1.0 Burla M.C., Caliandro R., Camalli M., Carrazzoni B., Cascarano G.L., De Caro L., Giacovazzo C. , Polidori G., Spagna R. ; _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '198 1.5 degree images with \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1412 _diffrn_reflns_av_sigmaI/netI 0.0816 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 45280 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 5.40 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.199 _exptl_absorpt_correction_T_max 0.9428 _exptl_absorpt_correction_T_min 0.9107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.139 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1440 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.543 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 425 _refine_ls_number_reflns 8750 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0565 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+1.4613P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1251 _refine_ls_wR_factor_ref 0.1522 _reflns_number_gt 5376 _reflns_number_total 8750 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file om100649z_si_002.cif _[local]_cod_data_source_block h09msh8 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 4063339 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ca Ca 0.87611(4) 0.19202(3) 0.79072(2) 0.02968(13) Uani 1 1 d . . . N1 N 0.95676(17) 0.24126(11) 0.70261(10) 0.0325(4) Uani 1 1 d . . . N2 N 0.75491(16) 0.28976(10) 0.72712(9) 0.0270(4) Uani 1 1 d . . . N3 N 0.73836(17) 0.23893(11) 0.85079(9) 0.0309(4) Uani 1 1 d . . . C1 C 1.0746(2) 0.22319(14) 0.69897(12) 0.0324(5) Uani 1 1 d . . . C2 C 1.1691(2) 0.26422(15) 0.74072(13) 0.0394(6) Uani 1 1 d . . . C3 C 1.1463(3) 0.33709(18) 0.77925(16) 0.0542(7) Uani 1 1 d . . . H3 H 1.0600 0.3392 0.7796 0.065 Uiso 1 1 calc R . . C4 C 1.2168(5) 0.3381(3) 0.8539(2) 0.1004(14) Uani 1 1 d . . . H4A H 1.1987 0.3859 0.8764 0.151 Uiso 1 1 calc R . . H4B H 1.3017 0.3363 0.8545 0.151 Uiso 1 1 calc R . . H4C H 1.1949 0.2928 0.8783 0.151 Uiso 1 1 calc R . . C5 C 1.1777(4) 0.4095(2) 0.7432(2) 0.0802(11) Uani 1 1 d . . . H5A H 1.1335 0.4095 0.6954 0.120 Uiso 1 1 calc R . . H5B H 1.2629 0.4096 0.7443 0.120 Uiso 1 1 calc R . . H5C H 1.1571 0.4559 0.7666 0.120 Uiso 1 1 calc R . . C6 C 1.2848(2) 0.23851(18) 0.74557(14) 0.0465(7) Uani 1 1 d . . . H6 H 1.3482 0.2654 0.7746 0.056 Uiso 1 1 calc R . . C7 C 1.3089(2) 0.17470(18) 0.70904(15) 0.0500(7) Uani 1 1 d . . . H7 H 1.3882 0.1571 0.7137 0.060 Uiso 1 1 calc R . . C8 C 1.2177(3) 0.13663(16) 0.66586(15) 0.0469(7) Uani 1 1 d . . . H8 H 1.2353 0.0936 0.6399 0.056 Uiso 1 1 calc R . . C9 C 1.1002(2) 0.15955(15) 0.65920(13) 0.0389(6) Uani 1 1 d . . . C10 C 1.0021(3) 0.11659(17) 0.61033(15) 0.0509(7) Uani 1 1 d . . . H10 H 0.9253 0.1413 0.6137 0.061 Uiso 1 1 calc R . . C11 C 1.0144(3) 0.1238(2) 0.53592(17) 0.0725(10) Uani 1 1 d . . . H11A H 1.0178 0.1789 0.5239 0.109 Uiso 1 1 calc R . . H11B H 0.9461 0.0993 0.5056 0.109 Uiso 1 1 calc R . . H11C H 1.0872 0.0977 0.5305 0.109 Uiso 1 1 calc R . . C12 C 0.9967(4) 0.0313(2) 0.6305(2) 0.0819(11) Uani 1 1 d . . . H12A H 0.9325 0.0053 0.5981 0.123 Uiso 1 1 calc R . . H12B H 0.9821 0.0278 0.6769 0.123 Uiso 1 1 calc R . . H12C H 1.0722 0.0059 0.6292 0.123 Uiso 1 1 calc R . . C13 C 0.8913(2) 0.28659(13) 0.65195(12) 0.0323(5) Uani 1 1 d . . . C14 C 0.9248(2) 0.31607(16) 0.59594(13) 0.0433(6) Uani 1 1 d . . . H14A H 1.0019 0.3057 0.5887 0.052 Uiso 1 1 calc R . . H14B H 0.8712 0.3470 0.5640 0.052 Uiso 1 1 calc R . . C15 C 0.7712(2) 0.30515(13) 0.66375(11) 0.0296(5) Uani 1 1 d . . . C16 C 0.6775(2) 0.33536(15) 0.61432(12) 0.0383(6) Uani 1 1 d . . . H16 H 0.6875 0.3462 0.5692 0.046 Uiso 1 1 calc R . . C17 C 0.5700(2) 0.34932(15) 0.63195(13) 0.0418(6) Uani 1 1 d . . . H17 H 0.5051 0.3685 0.5984 0.050 Uiso 1 1 calc R . . C18 C 0.5568(2) 0.33557(14) 0.69788(12) 0.0350(5) Uani 1 1 d . . . H18 H 0.4836 0.3460 0.7104 0.042 Uiso 1 1 calc R . . C19 C 0.65261(19) 0.30612(13) 0.74594(11) 0.0280(5) Uani 1 1 d . . . C20 C 0.65171(19) 0.29010(13) 0.81964(11) 0.0291(5) Uani 1 1 d . . . C21 C 0.5723(2) 0.32842(14) 0.84861(13) 0.0377(6) Uani 1 1 d . . . H21A H 0.5727 0.3211 0.8959 0.045 Uiso 1 1 calc R . . H21B H 0.5162 0.3625 0.8216 0.045 Uiso 1 1 calc R . . C22 C 0.7420(2) 0.22414(13) 0.92134(11) 0.0295(5) Uani 1 1 d . . . C23 C 0.6752(2) 0.16308(14) 0.94157(11) 0.0321(5) Uani 1 1 d . . . C24 C 0.5897(2) 0.11495(15) 0.88945(13) 0.0420(6) Uani 1 1 d . . . H24 H 0.5988 0.1309 0.8427 0.050 Uiso 1 1 calc R . . C25 C 0.4626(3) 0.1303(2) 0.89380(17) 0.0626(9) Uani 1 1 d . . . H25A H 0.4094 0.0988 0.8594 0.094 Uiso 1 1 calc R . . H25B H 0.4443 0.1856 0.8851 0.094 Uiso 1 1 calc R . . H25C H 0.4517 0.1166 0.9397 0.094 Uiso 1 1 calc R . . C26 C 0.6165(3) 0.02826(18) 0.89751(19) 0.0693(9) Uani 1 1 d . . . H26A H 0.6987 0.0188 0.8943 0.104 Uiso 1 1 calc R . . H26B H 0.5631 -0.0005 0.8611 0.104 Uiso 1 1 calc R . . H26C H 0.6050 0.0107 0.9423 0.104 Uiso 1 1 calc R . . C27 C 0.6844(2) 0.14793(14) 1.01118(12) 0.0349(5) Uani 1 1 d . . . H27 H 0.6394 0.1067 1.0246 0.042 Uiso 1 1 calc R . . C28 C 0.7578(2) 0.19186(16) 1.06113(12) 0.0393(6) Uani 1 1 d . . . H28 H 0.7629 0.1812 1.1084 0.047 Uiso 1 1 calc R . . C29 C 0.8234(2) 0.25110(16) 1.04159(12) 0.0403(6) Uani 1 1 d . . . H29 H 0.8742 0.2808 1.0760 0.048 Uiso 1 1 calc R . . C30 C 0.8172(2) 0.26874(14) 0.97290(12) 0.0365(5) Uani 1 1 d . . . C31 C 0.8887(3) 0.33699(17) 0.95488(14) 0.0486(7) Uani 1 1 d . . . H31 H 0.8748 0.3401 0.9037 0.058 Uiso 1 1 calc R . . C32 C 0.8493(3) 0.41314(19) 0.9806(2) 0.0724(10) Uani 1 1 d . . . H32A H 0.8967 0.4558 0.9680 0.109 Uiso 1 1 calc R . . H32B H 0.8602 0.4111 1.0307 0.109 Uiso 1 1 calc R . . H32C H 0.7655 0.4219 0.9599 0.109 Uiso 1 1 calc R . . C33 C 1.0217(3) 0.3244(2) 0.9829(3) 0.0867(12) Uani 1 1 d . . . H33A H 1.0658 0.3688 0.9702 0.130 Uiso 1 1 calc R . . H33B H 1.0469 0.2766 0.9634 0.130 Uiso 1 1 calc R . . H33C H 1.0374 0.3199 1.0330 0.130 Uiso 1 1 calc R . . O1 O 0.76655(17) 0.08622(10) 0.73384(10) 0.0503(5) Uani 1 1 d . . . C34 C 0.7716(3) 0.00426(18) 0.7488(2) 0.0660(9) Uani 1 1 d . . . H34A H 0.7860 -0.0043 0.7990 0.079 Uiso 1 1 calc R . . H34B H 0.8367 -0.0204 0.7314 0.079 Uiso 1 1 calc R . . C35 C 0.6555(3) -0.03011(19) 0.7143(2) 0.0725(10) Uani 1 1 d . . . H35A H 0.6661 -0.0679 0.6787 0.087 Uiso 1 1 calc R . . H35B H 0.6181 -0.0570 0.7481 0.087 Uiso 1 1 calc R . . C36 C 0.5822(3) 0.03665(19) 0.6830(2) 0.0807(12) Uani 1 1 d . . . H36A H 0.5345 0.0226 0.6372 0.097 Uiso 1 1 calc R . . H36B H 0.5283 0.0537 0.7125 0.097 Uiso 1 1 calc R . . C37 C 0.6685(4) 0.0985(2) 0.6773(2) 0.0821(12) Uani 1 1 d . . . H37A H 0.6940 0.0944 0.6332 0.099 Uiso 1 1 calc R . . H37B H 0.6333 0.1506 0.6802 0.099 Uiso 1 1 calc R . . O2 O 1.02464(16) 0.11869(13) 0.86166(10) 0.0549(5) Uani 1 1 d . . . C38 C 1.0136(3) 0.0809(2) 0.92434(16) 0.0697(10) Uani 1 1 d . . . H38A H 0.9426 0.0470 0.9163 0.084 Uiso 1 1 calc R . . H38B H 1.0064 0.1200 0.9597 0.084 Uiso 1 1 calc R . . C39 C 1.1228(3) 0.0337(2) 0.94704(16) 0.0713(10) Uani 1 1 d . . . H39A H 1.1042 -0.0168 0.9663 0.086 Uiso 1 1 calc R . . H39B H 1.1812 0.0618 0.9823 0.086 Uiso 1 1 calc R . . C40 C 1.1700(3) 0.0213(2) 0.88312(17) 0.0611(8) Uani 1 1 d . . . H40A H 1.2573 0.0160 0.8942 0.073 Uiso 1 1 calc R . . H40B H 1.1347 -0.0255 0.8578 0.073 Uiso 1 1 calc R . . C41 C 1.1329(3) 0.0925(3) 0.8435(2) 0.0981(16) Uani 1 1 d . . . H41A H 1.1950 0.1329 0.8549 0.118 Uiso 1 1 calc R . . H41B H 1.1189 0.0815 0.7937 0.118 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 Ca 0.0302(2) 0.0333(2) 0.0264(2) 0.00600(19) 0.00815(17) 0.0052(2) N1 0.0302(10) 0.0369(11) 0.0322(10) 0.0077(8) 0.0109(8) 0.0046(8) N2 0.0287(9) 0.0272(10) 0.0260(9) 0.0013(7) 0.0079(7) -0.0012(7) N3 0.0320(10) 0.0357(10) 0.0253(9) 0.0039(8) 0.0067(8) 0.0023(8) C1 0.0350(12) 0.0341(12) 0.0314(12) 0.0100(9) 0.0145(10) 0.0036(10) C2 0.0376(13) 0.0471(15) 0.0373(13) 0.0036(11) 0.0167(11) 0.0010(11) C3 0.0412(15) 0.0620(18) 0.0638(19) -0.0209(15) 0.0214(14) -0.0105(13) C4 0.145(4) 0.109(3) 0.054(2) -0.024(2) 0.038(2) -0.009(3) C5 0.111(3) 0.051(2) 0.078(3) -0.0113(17) 0.019(2) 0.006(2) C6 0.0338(14) 0.0639(18) 0.0431(15) 0.0072(13) 0.0114(11) 0.0017(12) C7 0.0403(15) 0.0657(19) 0.0477(16) 0.0176(14) 0.0175(13) 0.0190(13) C8 0.0566(17) 0.0435(15) 0.0480(16) 0.0086(12) 0.0277(13) 0.0154(13) C9 0.0460(14) 0.0372(13) 0.0384(13) 0.0065(10) 0.0197(11) 0.0036(11) C10 0.0543(17) 0.0475(16) 0.0560(17) -0.0105(13) 0.0227(14) -0.0040(13) C11 0.087(3) 0.081(2) 0.0506(19) -0.0156(17) 0.0186(17) -0.015(2) C12 0.104(3) 0.050(2) 0.100(3) -0.0053(18) 0.039(2) -0.0191(19) C13 0.0362(13) 0.0327(12) 0.0293(12) 0.0036(9) 0.0102(10) 0.0010(9) C14 0.0442(14) 0.0497(16) 0.0405(14) 0.0151(12) 0.0191(11) 0.0071(12) C15 0.0333(11) 0.0280(11) 0.0276(11) 0.0028(9) 0.0068(9) -0.0017(9) C16 0.0424(14) 0.0435(14) 0.0282(12) 0.0093(10) 0.0060(10) 0.0011(11) C17 0.0381(14) 0.0485(15) 0.0350(13) 0.0121(11) -0.0004(11) 0.0047(11) C18 0.0296(12) 0.0382(13) 0.0364(13) 0.0068(10) 0.0056(10) 0.0028(10) C19 0.0281(11) 0.0262(11) 0.0293(11) 0.0018(9) 0.0055(9) -0.0007(9) C20 0.0266(11) 0.0321(12) 0.0289(11) 0.0005(9) 0.0064(9) -0.0017(9) C21 0.0383(13) 0.0419(14) 0.0345(13) 0.0013(10) 0.0112(10) 0.0066(10) C22 0.0298(11) 0.0342(12) 0.0247(11) 0.0026(9) 0.0068(9) 0.0043(9) C23 0.0312(12) 0.0371(12) 0.0283(11) 0.0022(9) 0.0070(9) 0.0036(10) C24 0.0486(15) 0.0461(15) 0.0314(13) 0.0020(11) 0.0091(11) -0.0122(12) C25 0.0474(17) 0.076(2) 0.0595(19) 0.0041(16) 0.0002(14) -0.0120(15) C26 0.085(2) 0.0504(18) 0.068(2) -0.0156(15) 0.0065(18) -0.0067(17) C27 0.0364(13) 0.0394(13) 0.0307(12) 0.0064(10) 0.0112(10) 0.0027(10) C28 0.0432(14) 0.0511(15) 0.0245(11) 0.0050(11) 0.0091(10) 0.0033(12) C29 0.0417(14) 0.0506(15) 0.0279(12) -0.0047(10) 0.0055(10) -0.0019(11) C30 0.0418(14) 0.0398(13) 0.0284(12) -0.0011(10) 0.0087(10) -0.0010(11) C31 0.0571(17) 0.0538(16) 0.0352(14) -0.0029(12) 0.0104(12) -0.0184(13) C32 0.083(2) 0.0519(19) 0.087(3) -0.0035(17) 0.027(2) -0.0185(17) C33 0.058(2) 0.090(3) 0.120(3) 0.007(2) 0.038(2) -0.019(2) O1 0.0640(12) 0.0325(9) 0.0479(11) 0.0017(8) -0.0020(9) -0.0011(8) C34 0.069(2) 0.0414(16) 0.085(2) 0.0119(15) 0.0104(18) 0.0022(15) C35 0.089(3) 0.0455(18) 0.076(2) -0.0022(16) 0.000(2) -0.0094(17) C36 0.069(2) 0.0502(19) 0.109(3) -0.0104(19) -0.010(2) 0.0046(17) C37 0.095(3) 0.056(2) 0.073(2) 0.0120(17) -0.032(2) -0.0128(19) O2 0.0424(10) 0.0771(14) 0.0466(11) 0.0286(10) 0.0130(9) 0.0214(10) C38 0.073(2) 0.096(3) 0.0422(17) 0.0254(17) 0.0167(15) 0.0240(19) C39 0.103(3) 0.060(2) 0.0408(17) 0.0031(14) -0.0057(17) 0.0260(19) C40 0.0551(18) 0.063(2) 0.066(2) 0.0213(16) 0.0152(15) 0.0070(15) C41 0.068(2) 0.125(4) 0.116(3) 0.074(3) 0.052(2) 0.055(2) 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.2262 0.3064 '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' 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 N1 Ca N3 133.94(7) . . ? N1 Ca O2 106.94(7) . . ? N3 Ca O2 111.58(7) . . ? N1 Ca O1 100.26(7) . . ? N3 Ca O1 99.07(7) . . ? O2 Ca O1 97.11(7) . . ? N1 Ca N2 67.94(6) . . ? N3 Ca N2 68.93(6) . . ? O2 Ca N2 167.20(7) . . ? O1 Ca N2 95.39(6) . . ? N1 Ca C19 89.88(6) . . ? N3 Ca C19 48.31(6) . . ? O2 Ca C19 159.49(7) . . ? O1 Ca C19 91.15(6) . . ? N2 Ca C19 21.95(6) . . ? N1 Ca C15 47.76(6) . . ? N3 Ca C15 90.73(6) . . ? O2 Ca C15 154.62(7) . . ? O1 Ca C15 90.83(6) . . ? N2 Ca C15 21.85(6) . . ? C19 Ca C15 42.97(6) . . ? C13 N1 C1 118.20(19) . . ? C13 N1 Ca 121.23(15) . . ? C1 N1 Ca 120.55(14) . . ? C15 N2 C19 122.11(18) . . ? C15 N2 Ca 117.11(14) . . ? C19 N2 Ca 116.87(13) . . ? C20 N3 C22 115.08(19) . . ? C20 N3 Ca 119.98(14) . . ? C22 N3 Ca 124.69(14) . . ? C2 C1 N1 119.5(2) . . ? C2 C1 C9 119.1(2) . . ? N1 C1 C9 121.1(2) . . ? C6 C2 C1 119.5(2) . . ? C6 C2 C3 119.6(2) . . ? C1 C2 C3 120.9(2) . . ? C5 C3 C2 110.4(3) . . ? C5 C3 C4 108.6(3) . . ? C2 C3 C4 112.7(3) . . ? C5 C3 H3 108.3 . . ? C2 C3 H3 108.3 . . ? C4 C3 H3 108.3 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C2 121.1(3) . . ? C7 C6 H6 119.4 . . ? C2 C6 H6 119.4 . . ? C8 C7 C6 119.6(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 121.7(3) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C8 C9 C1 118.8(2) . . ? C8 C9 C10 120.1(2) . . ? C1 C9 C10 121.1(2) . . ? C9 C10 C12 111.4(3) . . ? C9 C10 C11 111.9(2) . . ? C12 C10 C11 110.6(3) . . ? C9 C10 H10 107.6 . . ? C12 C10 H10 107.6 . . ? C11 C10 H10 107.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 N1 127.6(2) . . ? C14 C13 C15 119.4(2) . . ? N1 C13 C15 112.98(19) . . ? C13 C14 H14A 120.0 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? N2 C15 C16 119.5(2) . . ? N2 C15 C13 115.51(18) . . ? C16 C15 C13 125.0(2) . . ? N2 C15 Ca 41.04(10) . . ? C16 C15 Ca 152.04(16) . . ? C13 C15 Ca 77.86(12) . . ? C17 C16 C15 119.1(2) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C18 C17 C16 120.3(2) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 118.9(2) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? N2 C19 C18 120.0(2) . . ? N2 C19 C20 115.37(18) . . ? C18 C19 C20 124.7(2) . . ? N2 C19 Ca 41.19(10) . . ? C18 C19 Ca 152.20(16) . . ? C20 C19 Ca 77.93(12) . . ? C21 C20 N3 127.7(2) . . ? C21 C20 C19 118.6(2) . . ? N3 C20 C19 113.68(19) . . ? C20 C21 H21A 120.0 . . ? C20 C21 H21B 120.0 . . ? H21A C21 H21B 120.0 . . ? C23 C22 C30 118.7(2) . . ? C23 C22 N3 121.0(2) . . ? C30 C22 N3 120.2(2) . . ? C27 C23 C22 119.7(2) . . ? C27 C23 C24 118.6(2) . . ? C22 C23 C24 121.7(2) . . ? C25 C24 C23 111.3(2) . . ? C25 C24 C26 110.0(3) . . ? C23 C24 C26 111.9(2) . . ? C25 C24 H24 107.8 . . ? C23 C24 H24 107.8 . . ? C26 C24 H24 107.8 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C23 121.2(2) . . ? C28 C27 H27 119.4 . . ? C23 C27 H27 119.4 . . ? C29 C28 C27 119.3(2) . . ? C29 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? C28 C29 C30 121.8(2) . . ? C28 C29 H29 119.1 . . ? C30 C29 H29 119.1 . . ? C29 C30 C22 119.3(2) . . ? C29 C30 C31 119.1(2) . . ? C22 C30 C31 121.6(2) . . ? C32 C31 C30 111.5(3) . . ? C32 C31 C33 110.5(3) . . ? C30 C31 C33 111.0(3) . . ? C32 C31 H31 107.9 . . ? C30 C31 H31 107.9 . . ? C33 C31 H31 107.9 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C37 O1 C34 107.3(2) . . ? C37 O1 Ca 121.08(17) . . ? C34 O1 Ca 131.32(17) . . ? O1 C34 C35 107.4(3) . . ? O1 C34 H34A 110.2 . . ? C35 C34 H34A 110.2 . . ? O1 C34 H34B 110.2 . . ? C35 C34 H34B 110.2 . . ? H34A C34 H34B 108.5 . . ? C36 C35 C34 105.3(3) . . ? C36 C35 H35A 110.7 . . ? C34 C35 H35A 110.7 . . ? C36 C35 H35B 110.7 . . ? C34 C35 H35B 110.7 . . ? H35A C35 H35B 108.8 . . ? C37 C36 C35 104.8(3) . . ? C37 C36 H36A 110.8 . . ? C35 C36 H36A 110.8 . . ? C37 C36 H36B 110.8 . . ? C35 C36 H36B 110.8 . . ? H36A C36 H36B 108.9 . . ? O1 C37 C36 105.4(3) . . ? O1 C37 H37A 110.7 . . ? C36 C37 H37A 110.7 . . ? O1 C37 H37B 110.7 . . ? C36 C37 H37B 110.7 . . ? H37A C37 H37B 108.8 . . ? C38 O2 C41 108.7(2) . . ? C38 O2 Ca 125.21(17) . . ? C41 O2 Ca 125.20(18) . . ? O2 C38 C39 106.4(3) . . ? O2 C38 H38A 110.5 . . ? C39 C38 H38A 110.5 . . ? O2 C38 H38B 110.5 . . ? C39 C38 H38B 110.5 . . ? H38A C38 H38B 108.6 . . ? C38 C39 C40 105.0(2) . . ? C38 C39 H39A 110.8 . . ? C40 C39 H39A 110.8 . . ? C38 C39 H39B 110.8 . . ? C40 C39 H39B 110.8 . . ? H39A C39 H39B 108.8 . . ? C41 C40 C39 102.8(3) . . ? C41 C40 H40A 111.2 . . ? C39 C40 H40A 111.2 . . ? C41 C40 H40B 111.2 . . ? C39 C40 H40B 111.2 . . ? H40A C40 H40B 109.1 . . ? O2 C41 C40 107.0(3) . . ? O2 C41 H41A 110.3 . . ? C40 C41 H41A 110.3 . . ? O2 C41 H41B 110.3 . . ? C40 C41 H41B 110.3 . . ? H41A C41 H41B 108.6 . . ? 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 Ca N1 2.321(2) . ? Ca N3 2.334(2) . ? Ca O2 2.3432(17) . ? Ca O1 2.3612(18) . ? Ca N2 2.3718(18) . ? Ca C19 3.213(2) . ? Ca C15 3.215(2) . ? N1 C13 1.368(3) . ? N1 C1 1.415(3) . ? N2 C15 1.344(3) . ? N2 C19 1.346(3) . ? N3 C20 1.376(3) . ? N3 C22 1.422(3) . ? C1 C2 1.411(4) . ? C1 C9 1.419(4) . ? C2 C6 1.393(4) . ? C2 C3 1.521(4) . ? C3 C5 1.519(5) . ? C3 C4 1.535(5) . ? C3 H3 1.0000 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.378(4) . ? C6 H6 0.9500 . ? C7 C8 1.375(4) . ? C7 H7 0.9500 . ? C8 C9 1.394(4) . ? C8 H8 0.9500 . ? C9 C10 1.518(4) . ? C10 C12 1.525(4) . ? C10 C11 1.527(4) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.358(3) . ? C13 C15 1.493(3) . ? C14 H14A 0.9500 . ? C14 H14B 0.9500 . ? C15 C16 1.398(3) . ? C16 C17 1.384(4) . ? C16 H16 0.9500 . ? C17 C18 1.377(4) . ? C17 H17 0.9500 . ? C18 C19 1.394(3) . ? C18 H18 0.9500 . ? C19 C20 1.499(3) . ? C20 C21 1.357(3) . ? C21 H21A 0.9500 . ? C21 H21B 0.9500 . ? C22 C23 1.412(3) . ? C22 C30 1.419(3) . ? C23 C27 1.395(3) . ? C23 C24 1.516(3) . ? C24 C25 1.515(4) . ? C24 C26 1.522(4) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.385(3) . ? C27 H27 0.9500 . ? C28 C29 1.374(4) . ? C28 H28 0.9500 . ? C29 C30 1.390(3) . ? C29 H29 0.9500 . ? C30 C31 1.522(4) . ? C31 C32 1.511(5) . ? C31 C33 1.535(5) . ? C31 H31 1.0000 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? O1 C37 1.432(4) . ? O1 C34 1.438(3) . ? C34 C35 1.492(5) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.482(5) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.479(5) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? O2 C38 1.439(3) . ? O2 C41 1.448(4) . ? C38 C39 1.486(4) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.507(5) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.469(4) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? _journal_paper_doi 10.1021/om100649z