#------------------------------------------------------------------------------ #$Date: 2014-08-18 08:24:34 +0300 (Mon, 18 Aug 2014) $ #$Revision: 122174 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/73/1517396.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_1517396 loop_ _publ_author_name 'Slater, Natasha H.' 'Brown, Natalie J.' 'Elsegood, Mark R. J.' 'Kimber, Marc C.' _publ_section_title ; The Au(I) Catalyzed Activation of Allenamides and Their Subsequent Transformation into Chromanes: A Method for the Regiocontrolled Addition to the \a- and \g-Positions of the Allene Unit. ; _journal_name_full 'Organic letters' _journal_page_first 140814102433005 _journal_paper_doi 10.1021/ol502178v _journal_year 2014 _chemical_formula_moiety 'C13 H15 N O3' _chemical_formula_sum 'C13 H15 N O3' _chemical_formula_weight 233.26 _chemical_name_systematic ; ? ; _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 difmap _atom_sites_solution_primary difmap _audit_creation_method SHELXL-2014 _cell_angle_alpha 69.1857(19) _cell_angle_beta 65.3217(18) _cell_angle_gamma 63.0462(19) _cell_formula_units_Z 4 _cell_length_a 10.7856(14) _cell_length_b 11.0756(15) _cell_length_c 12.1131(16) _cell_measurement_reflns_used 7519 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 31.39 _cell_measurement_theta_min 2.23 _cell_volume 1147.1(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX 2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.945 _diffrn_measurement_device_type 'Bruker APEX 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_unetI/netI 0.0244 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 17838 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.490 _diffrn_reflns_theta_min 1.890 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2012/1, Sheldrick, G.M., (2012)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.351 _exptl_crystal_description block _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.820 _exptl_crystal_size_mid 0.440 _exptl_crystal_size_min 0.290 _refine_diff_density_max 0.357 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 427 _refine_ls_number_reflns 7213 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0409 _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^)+(0.0665P)^2^+0.1874P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1100 _refine_ls_wR_factor_ref 0.1175 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5979 _reflns_number_total 7213 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file ol502178v_si_002.cif _[local]_cod_data_source_block 13 _cod_database_code 1517396 _diffrn_reflns_laue_measured_fraction_full 1.000 _diffrn_reflns_laue_measured_fraction_max 0.945 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.945 _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_min 0.925 _shelx_estimated_absorpt_t_max 0.973 _shelxl_version_number 2014-3 _shelx_res_file ; TITL mck29 in P-1 CELL 0.71073 10.7856 11.0756 12.1131 69.1857 65.3217 63.0462 ZERR 4.00 0.0014 0.0015 0.0016 0.0019 0.0018 0.0019 LATT 1 SFAC C H N O UNIT 52 60 4 12 TEMP -123 SIZE 0.29 0.44 0.82 ACTA CONF WPDB -1 L.S. 6 BOND $H FMAP 2 PLAN 10 REM EXTI 0.0018(16) insig. WGHT 0.066500 0.187400 FVAR 0.20635 N1 3 0.328363 0.651830 0.484152 11.00000 0.03051 0.02265 = 0.02259 0.00070 -0.01293 -0.01383 C1 1 0.343938 0.662167 0.586514 11.00000 0.02162 0.02861 = 0.02349 -0.00508 -0.00908 -0.00773 O1 4 0.395234 0.735852 0.591729 11.00000 0.04528 0.05608 = 0.03459 -0.00955 -0.01431 -0.03125 O2 4 0.293560 0.572523 0.687277 11.00000 0.03120 0.03384 = 0.02136 -0.00152 -0.01017 -0.01268 C2 1 0.251257 0.491141 0.648012 11.00000 0.03492 0.02190 = 0.02779 0.00165 -0.01143 -0.01128 H2A 2 0.328718 0.400777 0.646549 11.00000 0.03672 H2B 2 0.161587 0.480984 0.708160 11.00000 0.03330 C3 1 0.236542 0.571214 0.519988 11.00000 0.04530 0.02747 = 0.02951 0.00387 -0.01819 -0.02340 H3B 2 0.133398 0.635267 0.523141 11.00000 0.04223 H3A 2 0.267270 0.513934 0.463446 11.00000 0.04466 C4 1 0.343745 0.754159 0.372041 11.00000 0.02069 0.01958 = 0.02225 -0.00151 -0.00831 -0.00769 H4 2 0.419740 0.786924 0.362751 11.00000 0.01884 C5 1 0.377141 0.701466 0.259015 11.00000 0.02802 0.02051 = 0.02261 -0.00377 -0.00803 -0.00685 H5A 2 0.465203 0.616950 0.252465 11.00000 0.03695 H5B 2 0.295754 0.678700 0.266229 11.00000 0.03102 C6 1 0.400736 0.813952 0.143334 11.00000 0.02782 0.02227 = 0.02113 -0.00453 -0.00111 -0.00280 H6A 2 0.500360 0.818176 0.120434 11.00000 0.03454 H6B 2 0.395226 0.794987 0.070505 11.00000 0.04357 C7 1 0.287046 0.954630 0.164158 11.00000 0.01893 0.02062 = 0.01946 -0.00479 -0.00405 -0.00604 C8 1 0.196877 0.975412 0.283650 11.00000 0.01828 0.02088 = 0.01730 -0.00243 -0.00587 -0.00809 O3 4 0.206704 0.870885 0.388580 11.00000 0.02094 0.02257 = 0.01741 -0.00199 -0.00445 -0.00628 C9 1 0.090148 1.104574 0.302624 11.00000 0.02056 0.02473 = 0.01948 -0.00741 -0.00432 -0.00596 H9 2 0.031521 1.113307 0.387410 11.00000 0.03420 C10 1 0.076586 1.214960 0.202034 11.00000 0.02312 0.02091 = 0.02494 -0.00648 -0.00818 -0.00344 H10 2 0.003259 1.305226 0.215420 11.00000 0.02824 C11 1 0.166838 1.198777 0.081170 11.00000 0.02345 0.02164 = 0.02190 -0.00255 -0.00921 -0.00719 C12 1 0.269059 1.067546 0.064911 11.00000 0.02279 0.02385 = 0.01705 -0.00376 -0.00377 -0.00801 H12 2 0.329189 1.054298 -0.020679 11.00000 0.02902 C13 1 0.155001 1.319431 -0.027364 11.00000 0.03375 0.02294 = 0.02571 0.00031 -0.01208 -0.00709 H13A 2 0.055967 1.374113 -0.028145 11.00000 0.06605 H13B 2 0.206864 1.292270 -0.108876 11.00000 0.08935 H13C 2 0.198882 1.378289 -0.029932 11.00000 0.06356 N2 3 0.243369 0.120525 0.603676 11.00000 0.02425 0.02339 = 0.01961 0.00018 -0.00937 -0.01220 C14 1 0.263463 0.116764 0.708809 11.00000 0.01900 0.01755 = 0.01897 -0.00409 -0.00615 -0.00301 O4 4 0.340553 0.162635 0.718279 11.00000 0.02819 0.02940 = 0.02492 -0.00876 -0.00837 -0.01172 O5 4 0.183628 0.048632 0.808623 11.00000 0.02973 0.03045 = 0.02006 -0.00006 -0.00804 -0.01484 C15 1 0.116889 -0.007506 0.766000 11.00000 0.03758 0.03666 = 0.02560 0.00532 -0.01324 -0.02373 H15A 2 0.016352 0.010791 0.819641 11.00000 0.05464 H15B 2 0.174986 -0.111213 0.773317 11.00000 0.05067 C16 1 0.131382 0.065640 0.630811 11.00000 0.02868 0.02937 = 0.02600 0.00296 -0.01246 -0.01728 H16A 2 0.043220 0.139230 0.616964 11.00000 0.03376 H16B 2 0.161307 0.001826 0.577405 11.00000 0.04613 C17 1 0.304463 0.194579 0.484012 11.00000 0.01932 0.01844 = 0.01828 -0.00197 -0.00717 -0.00655 H17 2 0.375002 0.219810 0.490475 11.00000 0.01788 C18 1 0.373039 0.112180 0.383148 11.00000 0.02285 0.01902 = 0.02435 -0.00699 -0.00822 -0.00331 H18A 2 0.296981 0.091673 0.375184 11.00000 0.02795 H18B 2 0.449098 0.024317 0.406458 11.00000 0.03240 C19 1 0.438105 0.196993 0.259709 11.00000 0.02073 0.02489 = 0.02039 -0.00879 -0.00442 -0.00036 H19A 2 0.467811 0.150934 0.192191 11.00000 0.03565 H19B 2 0.526168 0.202283 0.261395 11.00000 0.02942 C20 1 0.327631 0.341167 0.236933 11.00000 0.01795 0.02277 = 0.01809 -0.00617 -0.00552 -0.00529 C21 1 0.207820 0.392899 0.335414 11.00000 0.01837 0.02003 = 0.01536 -0.00390 -0.00491 -0.00689 O6 4 0.185121 0.320217 0.457016 11.00000 0.02179 0.01896 = 0.01572 -0.00234 -0.00327 -0.00268 C22 1 0.101758 0.523784 0.314963 11.00000 0.01920 0.02148 = 0.02084 -0.00536 -0.00564 -0.00419 H22 2 0.018295 0.558684 0.386582 11.00000 0.02792 C23 1 0.116508 0.604570 0.195836 11.00000 0.02381 0.02278 = 0.02360 -0.00252 -0.01094 -0.00532 H23 2 0.041102 0.695284 0.181748 11.00000 0.03690 C24 1 0.236496 0.557678 0.094967 11.00000 0.02639 0.02834 = 0.01884 -0.00088 -0.00964 -0.01170 C25 1 0.339071 0.425993 0.118274 11.00000 0.02194 0.02988 = 0.01637 -0.00590 -0.00429 -0.00820 H25 2 0.424082 0.389979 0.047636 11.00000 0.03470 C26 1 0.252287 0.646760 -0.033917 11.00000 0.03786 0.03978 = 0.02077 0.00524 -0.01264 -0.01591 H26A 2 0.175480 0.669853 -0.061782 11.00000 0.08193 H26B 2 0.342594 0.604024 -0.094300 11.00000 0.08230 H26C 2 0.255310 0.736182 -0.038618 11.00000 0.07375 HKLF 4 REM mck29 in P-1 REM R1 = 0.0409 for 5979 Fo > 4sig(Fo) and 0.0502 for all 7213 data REM 427 parameters refined using 0 restraints END WGHT 0.0665 0.1874 REM Highest difference peak 0.357, deepest hole -0.268, 1-sigma level 0.050 Q1 1 0.1246 0.0296 0.7004 11.00000 0.05 0.36 Q2 1 0.3372 0.3852 0.1788 11.00000 0.05 0.35 Q3 1 0.0932 1.1613 0.2494 11.00000 0.05 0.34 Q4 1 0.2747 1.0160 0.1176 11.00000 0.05 0.34 Q5 1 0.1167 0.5608 0.2534 11.00000 0.05 0.33 Q6 1 0.1529 0.4604 0.3229 11.00000 0.05 0.32 Q7 1 0.2176 1.1384 0.0772 11.00000 0.05 0.32 Q8 1 0.2708 0.3650 0.2877 11.00000 0.05 0.32 Q9 1 0.2380 0.1319 0.6523 11.00000 0.05 0.32 Q10 1 0.1252 1.2058 0.1399 11.00000 0.05 0.31 ; _shelx_res_checksum 51953 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 N1 N 0.32836(9) 0.65183(9) 0.48415(8) 0.02337(17) Uani 1 1 d C1 C 0.34394(10) 0.66217(11) 0.58651(9) 0.02439(19) Uani 1 1 d O1 O 0.39523(10) 0.73585(10) 0.59173(8) 0.0392(2) Uani 1 1 d O2 O 0.29356(8) 0.57252(8) 0.68728(7) 0.02888(16) Uani 1 1 d C2 C 0.25126(13) 0.49114(11) 0.64801(10) 0.0292(2) Uani 1 1 d H2A H 0.3287(16) 0.4008(15) 0.6465(14) 0.037(4) Uiso 1 1 d H2B H 0.1616(16) 0.4810(14) 0.7082(13) 0.033(3) Uiso 1 1 d C3 C 0.23654(14) 0.57121(12) 0.51999(11) 0.0304(2) Uani 1 1 d H3B H 0.1334(17) 0.6353(16) 0.5231(14) 0.042(4) Uiso 1 1 d H3A H 0.2673(17) 0.5139(16) 0.4634(15) 0.045(4) Uiso 1 1 d C4 C 0.34375(10) 0.75416(10) 0.37204(9) 0.02087(17) Uani 1 1 d H4 H 0.4197(13) 0.7869(12) 0.3628(11) 0.019(3) Uiso 1 1 d C5 C 0.37714(11) 0.70147(10) 0.25901(9) 0.02458(19) Uani 1 1 d H5A H 0.4652(16) 0.6169(15) 0.2525(14) 0.037(4) Uiso 1 1 d H5B H 0.2958(15) 0.6787(14) 0.2662(13) 0.031(3) Uiso 1 1 d C6 C 0.40074(12) 0.81395(11) 0.14333(10) 0.0286(2) Uani 1 1 d H6A H 0.5004(16) 0.8182(14) 0.1204(13) 0.035(4) Uiso 1 1 d H6B H 0.3952(17) 0.7950(16) 0.0705(15) 0.044(4) Uiso 1 1 d C7 C 0.28705(10) 0.95463(10) 0.16416(8) 0.02058(17) Uani 1 1 d C8 C 0.19688(9) 0.97541(9) 0.28365(8) 0.01870(17) Uani 1 1 d O3 O 0.20670(7) 0.87089(7) 0.38858(6) 0.02211(14) Uani 1 1 d C9 C 0.09015(10) 1.10457(10) 0.30262(9) 0.02228(18) Uani 1 1 d H9 H 0.0315(15) 1.1133(14) 0.3874(14) 0.034(4) Uiso 1 1 d C10 C 0.07659(10) 1.21496(10) 0.20203(9) 0.02398(19) Uani 1 1 d H10 H 0.0033(15) 1.3052(14) 0.2154(12) 0.028(3) Uiso 1 1 d C11 C 0.16684(10) 1.19878(10) 0.08117(9) 0.02246(18) Uani 1 1 d C12 C 0.26906(10) 1.06755(10) 0.06491(9) 0.02238(18) Uani 1 1 d H12 H 0.3292(15) 1.0543(13) -0.0207(13) 0.029(3) Uiso 1 1 d C13 C 0.15500(13) 1.31943(11) -0.02736(10) 0.0293(2) Uani 1 1 d H13A H 0.056(2) 1.374(2) -0.0281(18) 0.066(5) Uiso 1 1 d H13B H 0.207(3) 1.292(2) -0.109(2) 0.089(7) Uiso 1 1 d H13C H 0.199(2) 1.3783(19) -0.0299(17) 0.064(5) Uiso 1 1 d N2 N 0.24337(9) 0.12052(8) 0.60368(7) 0.02136(16) Uani 1 1 d C14 C 0.26346(9) 0.11676(9) 0.70881(8) 0.01974(17) Uani 1 1 d O4 O 0.34055(8) 0.16264(8) 0.71828(7) 0.02589(15) Uani 1 1 d O5 O 0.18363(8) 0.04863(8) 0.80862(6) 0.02652(16) Uani 1 1 d C15 C 0.11689(13) -0.00751(13) 0.76600(10) 0.0313(2) Uani 1 1 d H15A H 0.0164(19) 0.0108(17) 0.8196(16) 0.055(5) Uiso 1 1 d H15B H 0.1750(19) -0.1112(18) 0.7733(15) 0.051(4) Uiso 1 1 d C16 C 0.13138(12) 0.06564(11) 0.63081(10) 0.0264(2) Uani 1 1 d H16A H 0.0432(16) 0.1392(14) 0.6170(13) 0.034(4) Uiso 1 1 d H16B H 0.1613(17) 0.0018(17) 0.5774(15) 0.046(4) Uiso 1 1 d C17 C 0.30446(9) 0.19458(9) 0.48401(8) 0.01880(16) Uani 1 1 d H17 H 0.3750(13) 0.2198(12) 0.4905(11) 0.018(3) Uiso 1 1 d C18 C 0.37304(10) 0.11218(10) 0.38315(9) 0.02266(18) Uani 1 1 d H18A H 0.2970(15) 0.0917(13) 0.3752(12) 0.028(3) Uiso 1 1 d H18B H 0.4491(15) 0.0243(14) 0.4065(13) 0.032(3) Uiso 1 1 d C19 C 0.43810(10) 0.19699(10) 0.25971(9) 0.02464(19) Uani 1 1 d H19A H 0.4678(16) 0.1509(15) 0.1922(13) 0.036(4) Uiso 1 1 d H19B H 0.5262(15) 0.2023(14) 0.2614(12) 0.029(3) Uiso 1 1 d C20 C 0.32763(9) 0.34117(10) 0.23693(8) 0.01983(17) Uani 1 1 d C21 C 0.20782(9) 0.39290(9) 0.33541(8) 0.01794(16) Uani 1 1 d O6 O 0.18512(7) 0.32022(7) 0.45702(6) 0.02201(14) Uani 1 1 d C22 C 0.10176(10) 0.52378(10) 0.31496(9) 0.02166(18) Uani 1 1 d H22 H 0.0183(14) 0.5587(13) 0.3866(12) 0.028(3) Uiso 1 1 d C23 C 0.11651(11) 0.60457(10) 0.19584(9) 0.02398(19) Uani 1 1 d H23 H 0.0411(16) 0.6953(15) 0.1817(13) 0.037(4) Uiso 1 1 d C24 C 0.23650(11) 0.55768(11) 0.09497(9) 0.02398(19) Uani 1 1 d C25 C 0.33907(10) 0.42599(11) 0.11827(9) 0.02342(19) Uani 1 1 d H25 H 0.4241(15) 0.3900(14) 0.0476(13) 0.035(4) Uiso 1 1 d C26 C 0.25229(14) 0.64676(14) -0.03392(10) 0.0342(2) Uani 1 1 d H26A H 0.175(2) 0.670(2) -0.062(2) 0.082(6) Uiso 1 1 d H26B H 0.343(2) 0.604(2) -0.094(2) 0.082(6) Uiso 1 1 d H26C H 0.255(2) 0.736(2) -0.0386(19) 0.074(6) Uiso 1 1 d 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 N1 0.0305(4) 0.0227(4) 0.0226(4) 0.0007(3) -0.0129(3) -0.0138(3) C1 0.0216(4) 0.0286(5) 0.0235(4) -0.0051(4) -0.0091(3) -0.0077(4) O1 0.0453(5) 0.0561(6) 0.0346(4) -0.0096(4) -0.0143(4) -0.0312(4) O2 0.0312(4) 0.0338(4) 0.0214(3) -0.0015(3) -0.0102(3) -0.0127(3) C2 0.0349(5) 0.0219(5) 0.0278(5) 0.0017(4) -0.0114(4) -0.0113(4) C3 0.0453(6) 0.0275(5) 0.0295(5) 0.0039(4) -0.0182(5) -0.0234(5) C4 0.0207(4) 0.0196(4) 0.0222(4) -0.0015(3) -0.0083(3) -0.0077(3) C5 0.0280(4) 0.0205(4) 0.0226(4) -0.0038(3) -0.0080(3) -0.0068(4) C6 0.0278(5) 0.0223(5) 0.0211(4) -0.0045(4) -0.0011(4) -0.0028(4) C7 0.0189(4) 0.0206(4) 0.0195(4) -0.0048(3) -0.0040(3) -0.0060(3) C8 0.0183(4) 0.0209(4) 0.0173(4) -0.0024(3) -0.0059(3) -0.0081(3) O3 0.0209(3) 0.0226(3) 0.0174(3) -0.0020(2) -0.0045(2) -0.0063(3) C9 0.0206(4) 0.0247(4) 0.0195(4) -0.0074(3) -0.0043(3) -0.0060(3) C10 0.0231(4) 0.0209(4) 0.0249(5) -0.0065(3) -0.0082(3) -0.0034(3) C11 0.0234(4) 0.0216(4) 0.0219(4) -0.0026(3) -0.0092(3) -0.0072(3) C12 0.0228(4) 0.0239(4) 0.0170(4) -0.0038(3) -0.0038(3) -0.0080(3) C13 0.0338(5) 0.0229(5) 0.0257(5) 0.0003(4) -0.0121(4) -0.0071(4) N2 0.0242(4) 0.0234(4) 0.0196(4) 0.0002(3) -0.0094(3) -0.0122(3) C14 0.0190(4) 0.0176(4) 0.0190(4) -0.0041(3) -0.0061(3) -0.0030(3) O4 0.0282(3) 0.0294(4) 0.0249(3) -0.0088(3) -0.0084(3) -0.0117(3) O5 0.0297(3) 0.0305(4) 0.0201(3) -0.0001(3) -0.0080(3) -0.0148(3) C15 0.0376(6) 0.0367(6) 0.0256(5) 0.0053(4) -0.0132(4) -0.0237(5) C16 0.0287(5) 0.0294(5) 0.0260(5) 0.0030(4) -0.0125(4) -0.0173(4) C17 0.0193(4) 0.0184(4) 0.0183(4) -0.0020(3) -0.0072(3) -0.0066(3) C18 0.0228(4) 0.0190(4) 0.0243(4) -0.0070(3) -0.0082(3) -0.0033(3) C19 0.0207(4) 0.0249(5) 0.0204(4) -0.0088(4) -0.0044(3) -0.0004(3) C20 0.0179(4) 0.0228(4) 0.0181(4) -0.0062(3) -0.0055(3) -0.0053(3) C21 0.0184(4) 0.0200(4) 0.0154(4) -0.0039(3) -0.0049(3) -0.0069(3) O6 0.0218(3) 0.0190(3) 0.0157(3) -0.0023(2) -0.0033(2) -0.0027(2) C22 0.0192(4) 0.0215(4) 0.0208(4) -0.0054(3) -0.0056(3) -0.0042(3) C23 0.0238(4) 0.0228(4) 0.0236(4) -0.0025(3) -0.0109(3) -0.0053(3) C24 0.0264(4) 0.0283(5) 0.0188(4) -0.0009(3) -0.0096(3) -0.0117(4) C25 0.0219(4) 0.0299(5) 0.0164(4) -0.0059(3) -0.0043(3) -0.0082(4) C26 0.0379(6) 0.0398(6) 0.0208(5) 0.0052(4) -0.0126(4) -0.0159(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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 C4 120.63(8) C1 N1 C3 110.75(8) C4 N1 C3 123.22(8) O1 C1 O2 122.72(9) O1 C1 N1 127.74(10) O2 C1 N1 109.53(8) C1 O2 C2 109.01(8) O2 C2 C3 104.84(8) O2 C2 H2A 106.8(8) C3 C2 H2A 113.1(9) O2 C2 H2B 108.9(8) C3 C2 H2B 113.6(8) H2A C2 H2B 109.3(12) N1 C3 C2 100.38(8) N1 C3 H3B 109.8(9) C2 C3 H3B 112.6(9) N1 C3 H3A 113.4(10) C2 C3 H3A 114.0(9) H3B C3 H3A 106.7(13) N1 C4 O3 106.67(7) N1 C4 C5 112.45(8) O3 C4 C5 110.03(7) N1 C4 H4 108.8(7) O3 C4 H4 106.8(7) C5 C4 H4 111.8(7) C4 C5 C6 108.79(8) C4 C5 H5A 109.9(9) C6 C5 H5A 110.2(9) C4 C5 H5B 110.5(8) C6 C5 H5B 109.4(8) H5A C5 H5B 108.0(11) C7 C6 C5 111.44(8) C7 C6 H6A 108.2(8) C5 C6 H6A 110.0(8) C7 C6 H6B 107.8(9) C5 C6 H6B 111.2(9) H6A C6 H6B 108.1(12) C8 C7 C12 118.08(8) C8 C7 C6 120.76(8) C12 C7 C6 121.15(8) O3 C8 C9 116.49(8) O3 C8 C7 122.75(8) C9 C8 C7 120.76(8) C8 O3 C4 114.55(7) C10 C9 C8 119.60(8) C10 C9 H9 123.1(8) C8 C9 H9 117.2(8) C9 C10 C11 121.26(9) C9 C10 H10 119.6(8) C11 C10 H10 119.1(8) C12 C11 C10 117.70(9) C12 C11 C13 121.07(9) C10 C11 C13 121.22(9) C11 C12 C7 122.54(8) C11 C12 H12 118.1(8) C7 C12 H12 119.4(8) C11 C13 H13A 113.4(11) C11 C13 H13B 113.7(13) H13A C13 H13B 104.9(17) C11 C13 H13C 111.4(11) H13A C13 H13C 108.7(15) H13B C13 H13C 104.0(16) C14 N2 C17 122.78(8) C14 N2 C16 112.09(8) C17 N2 C16 124.05(8) O4 C14 O5 122.24(8) O4 C14 N2 128.20(9) O5 C14 N2 109.55(8) C14 O5 C15 109.13(7) O5 C15 C16 105.51(8) O5 C15 H15A 107.1(10) C16 C15 H15A 113.9(10) O5 C15 H15B 107.4(9) C16 C15 H15B 111.0(9) H15A C15 H15B 111.4(13) N2 C16 C15 100.64(8) N2 C16 H16A 110.8(8) C15 C16 H16A 114.6(8) N2 C16 H16B 112.7(9) C15 C16 H16B 112.3(9) H16A C16 H16B 106.0(12) N2 C17 O6 106.23(7) N2 C17 C18 112.80(8) O6 C17 C18 110.38(7) N2 C17 H17 107.9(7) O6 C17 H17 108.4(7) C18 C17 H17 110.9(7) C17 C18 C19 109.43(8) C17 C18 H18A 109.4(8) C19 C18 H18A 109.0(8) C17 C18 H18B 108.9(8) C19 C18 H18B 110.9(8) H18A C18 H18B 109.1(11) C20 C19 C18 110.27(8) C20 C19 H19A 110.0(8) C18 C19 H19A 109.5(8) C20 C19 H19B 109.7(8) C18 C19 H19B 109.5(8) H19A C19 H19B 107.8(11) C21 C20 C25 117.79(8) C21 C20 C19 120.08(8) C25 C20 C19 122.12(8) O6 C21 C20 123.38(8) O6 C21 C22 115.91(8) C20 C21 C22 120.70(8) C21 O6 C17 116.90(7) C23 C22 C21 119.81(8) C23 C22 H22 121.0(8) C21 C22 H22 119.2(8) C22 C23 C24 121.27(9) C22 C23 H23 119.5(9) C24 C23 H23 119.2(9) C25 C24 C23 117.45(9) C25 C24 C26 121.67(9) C23 C24 C26 120.88(9) C24 C25 C20 122.96(9) C24 C25 H25 118.7(8) C20 C25 H25 118.3(8) C24 C26 H26A 113.1(13) C24 C26 H26B 112.5(13) H26A C26 H26B 108.6(18) C24 C26 H26C 112.4(12) H26A C26 H26C 104.8(17) H26B C26 H26C 104.9(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C1 1.3678(13) N1 C4 1.4299(12) N1 C3 1.4607(13) C1 O1 1.2047(13) C1 O2 1.3582(12) O2 C2 1.4510(14) C2 C3 1.5222(15) C2 H2A 0.971(15) C2 H2B 0.965(14) C3 H3B 1.005(16) C3 H3A 0.954(16) C4 O3 1.4494(11) C4 C5 1.5199(14) C4 H4 0.990(12) C5 C6 1.5262(14) C5 H5A 0.984(15) C5 H5B 0.981(14) C6 C7 1.5113(13) C6 H6A 1.011(14) C6 H6B 1.006(16) C7 C8 1.3972(12) C7 C12 1.3976(13) C8 O3 1.3866(11) C8 C9 1.3944(13) C9 C10 1.3888(14) C9 H9 0.968(15) C10 C11 1.4005(14) C10 H10 0.971(14) C11 C12 1.3915(13) C11 C13 1.5058(14) C12 H12 0.989(14) C13 H13A 0.96(2) C13 H13B 0.99(2) C13 H13C 0.950(19) N2 C14 1.3620(12) N2 C17 1.4337(12) N2 C16 1.4589(12) C14 O4 1.2110(12) C14 O5 1.3579(11) O5 C15 1.4545(13) C15 C16 1.5233(15) C15 H15A 0.972(18) C15 H15B 1.020(17) C16 H16A 0.964(14) C16 H16B 0.983(16) C17 O6 1.4507(11) C17 C18 1.5161(13) C17 H17 0.960(12) C18 C19 1.5277(14) C18 H18A 0.992(13) C18 H18B 0.987(14) C19 C20 1.5107(13) C19 H19A 0.980(15) C19 H19B 0.987(13) C20 C21 1.3959(12) C20 C25 1.4004(13) C21 O6 1.3829(10) C21 C22 1.3962(12) C22 C23 1.3885(13) C22 H22 0.992(13) C23 C24 1.3995(14) C23 H23 0.976(15) C24 C25 1.3915(14) C24 C26 1.5084(14) C25 H25 0.994(14) C26 H26A 0.92(2) C26 H26B 0.97(2) C26 H26C 0.99(2) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C4 N1 C1 O1 -14.27(16) C3 N1 C1 O1 -169.12(11) C4 N1 C1 O2 166.67(8) C3 N1 C1 O2 11.83(11) O1 C1 O2 C2 -175.02(10) N1 C1 O2 C2 4.10(11) C1 O2 C2 C3 -17.32(11) C1 N1 C3 C2 -21.27(11) C4 N1 C3 C2 -175.35(9) O2 C2 C3 N1 22.41(11) C1 N1 C4 O3 -79.91(10) C3 N1 C4 O3 71.72(11) C1 N1 C4 C5 159.39(9) C3 N1 C4 C5 -48.99(13) N1 C4 C5 C6 -176.63(8) O3 C4 C5 C6 64.62(10) C4 C5 C6 C7 -43.86(12) C5 C6 C7 C8 13.10(14) C5 C6 C7 C12 -166.99(9) C12 C7 C8 O3 -179.28(8) C6 C7 C8 O3 0.63(14) C12 C7 C8 C9 1.29(14) C6 C7 C8 C9 -178.79(9) C9 C8 O3 C4 -161.33(8) C7 C8 O3 C4 19.22(12) N1 C4 O3 C8 -174.06(7) C5 C4 O3 C8 -51.83(10) O3 C8 C9 C10 178.38(8) C7 C8 C9 C10 -2.16(14) C8 C9 C10 C11 0.93(15) C9 C10 C11 C12 1.11(15) C9 C10 C11 C13 -178.20(10) C10 C11 C12 C7 -2.02(15) C13 C11 C12 C7 177.30(9) C8 C7 C12 C11 0.84(14) C6 C7 C12 C11 -179.07(9) C17 N2 C14 O4 -6.08(15) C16 N2 C14 O4 -174.65(9) C17 N2 C14 O5 175.12(8) C16 N2 C14 O5 6.56(11) O4 C14 O5 C15 -173.33(9) N2 C14 O5 C15 5.55(11) C14 O5 C15 C16 -14.65(11) C14 N2 C16 C15 -14.78(11) C17 N2 C16 C15 176.83(9) O5 C15 C16 N2 17.00(11) C14 N2 C17 O6 -103.52(9) C16 N2 C17 O6 63.67(11) C14 N2 C17 C18 135.43(9) C16 N2 C17 C18 -57.38(12) N2 C17 C18 C19 -178.80(7) O6 C17 C18 C19 62.54(10) C17 C18 C19 C20 -49.41(10) C18 C19 C20 C21 18.62(12) C18 C19 C20 C25 -160.13(9) C25 C20 C21 O6 -179.10(8) C19 C20 C21 O6 2.10(14) C25 C20 C21 C22 1.38(14) C19 C20 C21 C22 -177.41(9) C20 C21 O6 C17 10.21(13) C22 C21 O6 C17 -170.25(8) N2 C17 O6 C21 -165.04(7) C18 C17 O6 C21 -42.44(10) O6 C21 C22 C23 179.37(8) C20 C21 C22 C23 -1.08(14) C21 C22 C23 C24 -0.23(15) C22 C23 C24 C25 1.14(15) C22 C23 C24 C26 -179.41(10) C23 C24 C25 C20 -0.80(15) C26 C24 C25 C20 179.75(10) C21 C20 C25 C24 -0.44(15) C19 C20 C25 C24 178.34(9)