#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:06:36 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247601 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/57/7125706.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_7125706 loop_ _publ_author_name 'Fu, Wei' 'Wang, Lianhui' 'Yang, Zi' 'Shen, Jiang-Shan' 'Tang, Fei' 'Zhang, Jiayi' 'Cui, Xiuling' _publ_section_title ; Facile access to versatile aza-macrolides through iridium-catalysed cascade allyl-amination/macrolactonization. ; _journal_issue 6 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 960 _journal_page_last 963 _journal_paper_doi 10.1039/c9cc07372h _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C24 H26 N2 O6' _chemical_formula_sum 'C24 H26 N2 O6' _chemical_formula_weight 438.47 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens mixed _audit_creation_date 2019-11-02 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2019-11-04 deposited with the CCDC. 2019-12-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 11.5668(5) _cell_length_b 17.1785(9) _cell_length_c 23.0513(10) _cell_measurement_reflns_used 4025 _cell_measurement_temperature 293.1(2) _cell_measurement_theta_max 24.7610 _cell_measurement_theta_min 3.7180 _cell_volume 4580.3(4) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _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 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293.1(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.1213 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.875 _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 3.00 83.00 0.80 5.00 -- 15.49 57.00 -60.00 100 2 \w 37.00 72.20 0.80 5.00 -- 15.49 178.00 0.00 44 3 \w -21.00 22.20 0.80 5.00 -- -16.28 -99.00 120.00 54 4 \w 56.00 80.80 0.80 5.00 -- 15.49-147.00 71.00 31 5 \w -2.00 50.00 0.80 5.00 -- 15.49-124.00-123.00 65 6 \w -21.00 9.40 0.80 5.00 -- -16.28 -99.00-120.00 38 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0224015000 _diffrn_orient_matrix_UB_12 -0.0382268000 _diffrn_orient_matrix_UB_13 0.0032334000 _diffrn_orient_matrix_UB_21 -0.0024509000 _diffrn_orient_matrix_UB_22 -0.0052846000 _diffrn_orient_matrix_UB_23 -0.0304831000 _diffrn_orient_matrix_UB_31 0.0569943000 _diffrn_orient_matrix_UB_32 0.0147763000 _diffrn_orient_matrix_UB_33 -0.0025919000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_unetI/netI 0.0506 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.875 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 25391 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.875 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.492 _diffrn_reflns_theta_min 3.443 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.36759 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.272 _exptl_crystal_description prism _exptl_crystal_F_000 1856 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.290 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 299 _refine_ls_number_reflns 5572 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.1159 _refine_ls_R_factor_gt 0.0608 _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^)+(0.0680P)^2^+0.9273P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1341 _refine_ls_wR_factor_ref 0.1672 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3156 _reflns_number_total 5572 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc07372h2.cif _cod_data_source_block syn-3g _cod_depositor_comments 'Adding full bibliography for 7125703--7125707.cif.' _cod_database_code 7125706 _shelx_shelxl_version_number 2018/1 _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 99.62 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _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. Uiso/Uaniso restraints and constraints Uanis(C23) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 3.a Ternary CH refined with riding coordinates: C8(H8), C18(H18) 3.b Secondary CH2 refined with riding coordinates: C21(H21A,H21B), C22(H22A,H22B) 3.c Aromatic/amide H refined with riding coordinates: C3(H3), C5(H5), C6(H6), C9(H9), C13(H13), C15(H15), C16(H16), C19(H19) 3.d X=CH2 refined with riding coordinates: C10(H10A,H10B), C20(H20A,H20B) 3.e Idealised Me refined as rotating group: C23(H23A,H23B,H23C), C24(H24A,H24B,H24C) ; _shelx_res_file ; TITL exp_7054_a.res in Pbca syn-3g.res created by SHELXL-2018/1 at 14:57:58 on 02-Nov-2019 REM Old TITL exp_7054 in Pbca REM SHELXT solution in Pbca REM R1 0.208, Rweak 0.344, Alpha 0.023, Orientation as input REM Formula found by SHELXT: C20 N4 O6 CELL 0.71073 11.5668 17.1785 23.0513 90 90 90 ZERR 8 0.0005 0.0009 0.001 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 192 208 16 48 ISOR 0.005 0.01 C23 L.S. 10 PLAN 5 TEMP 20.0(2) BOND $H list 4 fmap 2 acta REM REM REM WGHT 0.068000 0.927300 FVAR 0.41042 O1 4 0.795320 0.683553 0.568502 11.00000 0.05137 0.04620 = 0.05706 0.01709 -0.00659 -0.00903 O2 4 0.690394 0.593918 0.520703 11.00000 0.07061 0.05970 = 0.04235 0.00694 -0.00655 -0.00691 O3 4 0.374892 0.570723 0.626517 11.00000 0.05462 0.03782 = 0.04999 -0.00500 0.00946 -0.00401 O4 4 0.443978 0.615746 0.541627 11.00000 0.05833 0.05117 = 0.03815 -0.00450 -0.00128 -0.00046 O5 4 0.995077 0.529119 0.725825 11.00000 0.06906 0.05812 = 0.08406 0.01286 -0.03571 -0.00856 O6 4 0.288528 0.805121 0.746373 11.00000 0.11354 0.06413 = 0.08466 -0.03183 0.04392 -0.00794 N1 3 0.589457 0.490567 0.598768 11.00000 0.04582 0.05344 = 0.04248 0.01114 -0.00181 -0.00881 N2 3 0.565612 0.753328 0.552952 11.00000 0.05002 0.04991 = 0.05157 -0.00185 0.00396 -0.00832 C1 1 0.691241 0.502317 0.628092 11.00000 0.04074 0.03652 = 0.03776 -0.00215 0.00084 0.00162 C2 1 0.771360 0.560796 0.612605 11.00000 0.04329 0.03618 = 0.03886 0.00094 0.00160 0.00106 C3 1 0.873074 0.571686 0.645068 11.00000 0.04547 0.03813 = 0.05428 0.00285 -0.00248 -0.00353 AFIX 43 H3 2 0.924933 0.610598 0.634597 11.00000 -1.20000 AFIX 0 C4 1 0.896372 0.524981 0.692356 11.00000 0.05106 0.03967 = 0.05274 -0.00105 -0.01382 0.00343 C5 1 0.818282 0.467877 0.707651 11.00000 0.05626 0.04547 = 0.04899 0.00770 -0.00494 0.00588 AFIX 43 H5 2 0.833656 0.436458 0.739588 11.00000 -1.20000 AFIX 0 C6 1 0.718910 0.456545 0.676867 11.00000 0.04867 0.04126 = 0.05117 0.01035 0.00310 -0.00211 AFIX 43 H6 2 0.668085 0.417554 0.688399 11.00000 -1.20000 AFIX 0 C7 1 0.748202 0.612106 0.562504 11.00000 0.04011 0.04588 = 0.04286 0.00504 0.00535 -0.00118 C8 1 0.489624 0.451134 0.623398 11.00000 0.04749 0.04349 = 0.04186 -0.00084 0.00369 -0.00727 AFIX 13 H8 2 0.494860 0.453907 0.665780 11.00000 -1.20000 AFIX 0 C9 1 0.484149 0.366710 0.605812 11.00000 0.06371 0.04438 = 0.06098 -0.00227 0.00746 -0.00423 AFIX 43 H9 2 0.490788 0.355576 0.566471 11.00000 -1.20000 AFIX 0 C10 1 0.471189 0.309169 0.640239 11.00000 0.15134 0.05583 = 0.10581 0.00627 0.01968 -0.01244 AFIX 93 H10A 2 0.464203 0.317683 0.679927 11.00000 -1.20000 H10B 2 0.468733 0.258730 0.625634 11.00000 -1.20000 AFIX 0 C11 1 0.492121 0.763784 0.599490 11.00000 0.04225 0.04135 = 0.04528 0.00121 -0.00384 -0.00147 C12 1 0.418797 0.703943 0.620281 11.00000 0.04019 0.03968 = 0.04208 -0.00413 -0.00283 0.00067 C13 1 0.350871 0.716758 0.669871 11.00000 0.05005 0.04565 = 0.05298 -0.00730 0.00915 -0.00390 AFIX 43 H13 2 0.304248 0.676924 0.683982 11.00000 -1.20000 AFIX 0 C14 1 0.352439 0.787527 0.697844 11.00000 0.06294 0.05025 = 0.06003 -0.01769 0.01053 -0.00081 C15 1 0.421748 0.846871 0.676568 11.00000 0.07256 0.04222 = 0.07472 -0.01783 0.00326 -0.00410 AFIX 43 H15 2 0.422001 0.895007 0.695031 11.00000 -1.20000 AFIX 0 C16 1 0.489764 0.835513 0.628761 11.00000 0.05859 0.03855 = 0.06587 -0.00060 0.00132 -0.00835 AFIX 43 H16 2 0.535510 0.876217 0.615321 11.00000 -1.20000 AFIX 0 C17 1 0.414396 0.627641 0.591546 11.00000 0.03494 0.04047 = 0.04171 -0.00422 -0.00310 -0.00033 C18 1 0.673785 0.795971 0.547000 11.00000 0.04968 0.04676 = 0.05270 0.01236 0.00047 -0.00719 AFIX 13 H18 2 0.696748 0.812513 0.586022 11.00000 -1.20000 AFIX 0 C19 1 0.667303 0.868257 0.510132 11.00000 0.06853 0.06592 = 0.07696 0.02490 0.00694 0.00064 AFIX 43 H19 2 0.734278 0.898032 0.507704 11.00000 -1.20000 AFIX 0 C20 1 0.581457 0.892605 0.482388 11.00000 0.11806 0.09998 = 0.10756 0.04752 -0.02515 -0.00096 AFIX 93 H20A 2 0.512284 0.865038 0.483324 11.00000 -1.20000 H20B 2 0.586913 0.938243 0.460861 11.00000 -1.20000 AFIX 0 C21 1 0.378353 0.491624 0.604278 11.00000 0.04809 0.03905 = 0.05652 -0.00950 0.00253 -0.00717 AFIX 23 H21A 2 0.374420 0.492579 0.562250 11.00000 -1.20000 H21B 2 0.312093 0.462824 0.618582 11.00000 -1.20000 AFIX 0 C22 1 0.768168 0.741842 0.524720 11.00000 0.05239 0.05411 = 0.05846 0.02314 0.00487 -0.00697 AFIX 23 H22A 2 0.742307 0.716368 0.489479 11.00000 -1.20000 H22B 2 0.836949 0.771775 0.515669 11.00000 -1.20000 AFIX 0 C23 1 1.073366 0.587938 0.714641 11.00000 0.11124 0.10043 = 0.20424 0.07043 -0.09994 -0.05275 AFIX 137 H23A 2 1.111009 0.578221 0.678238 11.00000 -1.50000 H23B 2 1.130052 0.589599 0.745035 11.00000 -1.50000 H23C 2 1.033456 0.636880 0.712876 11.00000 -1.50000 AFIX 0 C24 1 0.232877 0.745945 0.776092 11.00000 0.11260 0.07753 = 0.08133 -0.02078 0.04575 -0.00745 AFIX 137 H24A 2 0.171946 0.725159 0.752434 11.00000 -1.50000 H24B 2 0.200844 0.766184 0.811427 11.00000 -1.50000 H24C 2 0.287254 0.705462 0.785020 11.00000 -1.50000 AFIX 0 H2 2 0.559612 0.709690 0.536351 11.00000 0.05259 H1 2 0.581794 0.515772 0.568608 11.00000 0.05090 HKLF 4 REM exp_7054_a.res in Pbca REM R1 = 0.0608 for 3156 Fo > 4sig(Fo) and 0.1159 for all 5572 data REM 299 parameters refined using 6 restraints END WGHT 0.0680 0.9273 REM Highest difference peak 0.290, deepest hole -0.304, 1-sigma level 0.063 Q1 1 0.6653 0.9236 0.4936 11.00000 0.05 0.29 Q2 1 0.6386 0.8350 0.4745 11.00000 0.05 0.26 Q3 1 0.2794 0.6685 0.6676 11.00000 0.05 0.19 Q4 1 0.6066 0.8828 0.6199 11.00000 0.05 0.18 Q5 1 0.5954 0.4223 0.7002 11.00000 0.05 0.17 ; _shelx_res_checksum 82436 _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 2.169 _oxdiff_exptl_absorpt_empirical_full_min 0.646 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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 O1 O 0.79532(12) 0.68355(9) 0.56850(6) 0.0515(4) Uani 1 1 d . . O2 O 0.69039(14) 0.59392(10) 0.52070(6) 0.0576(4) Uani 1 1 d . . O3 O 0.37489(12) 0.57072(8) 0.62652(6) 0.0475(4) Uani 1 1 d . . O4 O 0.44398(12) 0.61575(9) 0.54163(6) 0.0492(4) Uani 1 1 d . . O5 O 0.99508(15) 0.52912(11) 0.72583(8) 0.0704(5) Uani 1 1 d . . O6 O 0.28853(19) 0.80512(12) 0.74637(8) 0.0874(7) Uani 1 1 d . . N1 N 0.58946(15) 0.49057(12) 0.59877(8) 0.0472(5) Uani 1 1 d . . N2 N 0.56561(16) 0.75333(13) 0.55295(8) 0.0505(5) Uani 1 1 d . . C1 C 0.69124(16) 0.50232(12) 0.62809(8) 0.0383(5) Uani 1 1 d . . C2 C 0.77136(17) 0.56080(12) 0.61261(8) 0.0394(5) Uani 1 1 d . . C3 C 0.87307(17) 0.57169(12) 0.64507(9) 0.0460(5) Uani 1 1 d . . H3 H 0.924933 0.610598 0.634597 0.055 Uiso 1 1 calc R . C4 C 0.89637(18) 0.52498(13) 0.69236(9) 0.0478(5) Uani 1 1 d . . C5 C 0.81828(19) 0.46788(13) 0.70765(9) 0.0502(6) Uani 1 1 d . . H5 H 0.833656 0.436458 0.739588 0.060 Uiso 1 1 calc R . C6 C 0.71891(18) 0.45654(13) 0.67687(9) 0.0470(5) Uani 1 1 d . . H6 H 0.668085 0.417554 0.688399 0.056 Uiso 1 1 calc R . C7 C 0.74820(17) 0.61211(13) 0.56250(9) 0.0430(5) Uani 1 1 d . . C8 C 0.48962(17) 0.45113(12) 0.62340(9) 0.0443(5) Uani 1 1 d . . H8 H 0.494860 0.453907 0.665780 0.053 Uiso 1 1 calc R . C9 C 0.4841(2) 0.36671(14) 0.60581(11) 0.0564(6) Uani 1 1 d . . H9 H 0.490788 0.355576 0.566471 0.068 Uiso 1 1 calc R . C10 C 0.4712(3) 0.30917(19) 0.64024(16) 0.1043(11) Uani 1 1 d . . H10A H 0.464203 0.317683 0.679927 0.125 Uiso 1 1 calc R . H10B H 0.468733 0.258730 0.625634 0.125 Uiso 1 1 calc R . C11 C 0.49212(17) 0.76378(13) 0.59949(9) 0.0430(5) Uani 1 1 d . . C12 C 0.41880(16) 0.70394(12) 0.62028(8) 0.0406(5) Uani 1 1 d . . C13 C 0.35087(18) 0.71676(13) 0.66987(9) 0.0496(5) Uani 1 1 d . . H13 H 0.304248 0.676924 0.683982 0.059 Uiso 1 1 calc R . C14 C 0.3524(2) 0.78753(14) 0.69784(10) 0.0577(6) Uani 1 1 d . . C15 C 0.4217(2) 0.84687(14) 0.67657(11) 0.0632(7) Uani 1 1 d . . H15 H 0.422001 0.895007 0.695031 0.076 Uiso 1 1 calc R . C16 C 0.4898(2) 0.83551(14) 0.62876(10) 0.0543(6) Uani 1 1 d . . H16 H 0.535510 0.876217 0.615321 0.065 Uiso 1 1 calc R . C17 C 0.41440(16) 0.62764(12) 0.59155(9) 0.0390(5) Uani 1 1 d . . C18 C 0.67378(18) 0.79597(13) 0.54700(10) 0.0497(6) Uani 1 1 d . . H18 H 0.696748 0.812513 0.586022 0.060 Uiso 1 1 calc R . C19 C 0.6673(2) 0.86826(16) 0.51013(12) 0.0705(8) Uani 1 1 d . . H19 H 0.734278 0.898032 0.507704 0.085 Uiso 1 1 calc R . C20 C 0.5815(3) 0.8926(2) 0.48239(16) 0.1085(12) Uani 1 1 d . . H20A H 0.512284 0.865038 0.483324 0.130 Uiso 1 1 calc R . H20B H 0.586913 0.938243 0.460861 0.130 Uiso 1 1 calc R . C21 C 0.37835(18) 0.49162(12) 0.60428(10) 0.0479(5) Uani 1 1 d . . H21A H 0.374420 0.492579 0.562250 0.057 Uiso 1 1 calc R . H21B H 0.312093 0.462824 0.618582 0.057 Uiso 1 1 calc R . C22 C 0.76817(19) 0.74184(14) 0.52472(10) 0.0550(6) Uani 1 1 d . . H22A H 0.742307 0.716368 0.489479 0.066 Uiso 1 1 calc R . H22B H 0.836949 0.771775 0.515669 0.066 Uiso 1 1 calc R . C23 C 1.0734(3) 0.5879(2) 0.7146(2) 0.1386(18) Uani 1 1 d . U H23A H 1.111009 0.578221 0.678238 0.208 Uiso 1 1 calc GR . H23B H 1.130052 0.589599 0.745035 0.208 Uiso 1 1 calc GR . H23C H 1.033456 0.636880 0.712876 0.208 Uiso 1 1 calc GR . C24 C 0.2329(3) 0.74595(19) 0.77609(13) 0.0905(10) Uani 1 1 d . . H24A H 0.171946 0.725159 0.752434 0.136 Uiso 1 1 calc GR . H24B H 0.200844 0.766184 0.811427 0.136 Uiso 1 1 calc GR . H24C H 0.287254 0.705462 0.785020 0.136 Uiso 1 1 calc GR . H2 H 0.560(2) 0.7097(15) 0.5364(10) 0.053(7) Uiso 1 1 d . . H1 H 0.5818(18) 0.5158(14) 0.5686(10) 0.051(7) 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 O1 0.0514(8) 0.0462(9) 0.0571(9) 0.0171(7) -0.0066(7) -0.0090(7) O2 0.0706(10) 0.0597(11) 0.0424(9) 0.0069(7) -0.0066(8) -0.0069(9) O3 0.0546(9) 0.0378(9) 0.0500(9) -0.0050(6) 0.0095(7) -0.0040(7) O4 0.0583(9) 0.0512(10) 0.0381(8) -0.0045(7) -0.0013(7) -0.0005(8) O5 0.0691(11) 0.0581(11) 0.0841(12) 0.0129(9) -0.0357(9) -0.0086(9) O6 0.1135(15) 0.0641(13) 0.0847(13) -0.0318(10) 0.0439(12) -0.0079(12) N1 0.0458(10) 0.0534(12) 0.0425(11) 0.0111(9) -0.0018(8) -0.0088(9) N2 0.0500(11) 0.0499(13) 0.0516(11) -0.0018(10) 0.0040(9) -0.0083(10) C1 0.0407(10) 0.0365(11) 0.0378(11) -0.0021(8) 0.0008(8) 0.0016(9) C2 0.0433(11) 0.0362(11) 0.0389(11) 0.0009(8) 0.0016(8) 0.0011(9) C3 0.0455(11) 0.0381(12) 0.0543(13) 0.0028(10) -0.0025(10) -0.0035(10) C4 0.0511(12) 0.0397(12) 0.0527(13) -0.0011(10) -0.0138(10) 0.0034(11) C5 0.0563(13) 0.0455(13) 0.0490(13) 0.0077(10) -0.0049(10) 0.0059(11) C6 0.0487(12) 0.0413(12) 0.0512(13) 0.0104(10) 0.0031(10) -0.0021(10) C7 0.0401(10) 0.0459(13) 0.0429(12) 0.0050(10) 0.0054(9) -0.0012(10) C8 0.0475(11) 0.0435(13) 0.0419(11) -0.0008(9) 0.0037(9) -0.0073(10) C9 0.0637(15) 0.0444(14) 0.0610(14) -0.0023(11) 0.0075(11) -0.0042(12) C10 0.151(3) 0.056(2) 0.106(3) 0.0063(18) 0.020(2) -0.012(2) C11 0.0422(11) 0.0413(12) 0.0453(12) 0.0012(9) -0.0038(9) -0.0015(10) C12 0.0402(10) 0.0397(12) 0.0421(11) -0.0041(9) -0.0028(8) 0.0007(9) C13 0.0500(12) 0.0456(13) 0.0530(13) -0.0073(10) 0.0092(10) -0.0039(11) C14 0.0629(14) 0.0502(15) 0.0600(15) -0.0177(12) 0.0105(12) -0.0008(13) C15 0.0726(16) 0.0422(14) 0.0747(17) -0.0178(12) 0.0033(13) -0.0041(13) C16 0.0586(14) 0.0385(13) 0.0659(15) -0.0006(11) 0.0013(12) -0.0083(11) C17 0.0349(10) 0.0405(12) 0.0417(12) -0.0042(9) -0.0031(8) -0.0003(9) C18 0.0497(12) 0.0468(13) 0.0527(13) 0.0124(10) 0.0005(10) -0.0072(11) C19 0.0685(16) 0.0659(18) 0.0770(18) 0.0249(14) 0.0069(14) 0.0006(15) C20 0.118(3) 0.100(3) 0.108(3) 0.048(2) -0.025(2) -0.001(2) C21 0.0481(12) 0.0390(12) 0.0565(13) -0.0095(10) 0.0025(10) -0.0072(10) C22 0.0524(13) 0.0541(15) 0.0585(14) 0.0231(11) 0.0049(11) -0.0070(12) C23 0.111(3) 0.100(3) 0.204(4) 0.070(3) -0.100(3) -0.053(2) C24 0.113(2) 0.078(2) 0.081(2) -0.0208(17) 0.0457(19) -0.0074(19) 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 C7 O1 C22 117.85(17) C17 O3 C21 117.28(16) C4 O5 C23 118.4(2) C14 O6 C24 119.4(2) C1 N1 C8 123.87(18) C1 N1 H1 115.5(16) C8 N1 H1 119.3(16) C11 N2 C18 122.5(2) C11 N2 H2 114.6(16) C18 N2 H2 118.3(16) N1 C1 C2 122.88(18) N1 C1 C6 120.39(19) C6 C1 C2 116.72(18) C1 C2 C7 120.19(18) C3 C2 C1 120.58(18) C3 C2 C7 119.22(18) C2 C3 H3 119.8 C4 C3 C2 120.4(2) C4 C3 H3 119.8 O5 C4 C3 125.0(2) C5 C4 O5 115.82(19) C5 C4 C3 119.2(2) C4 C5 H5 119.3 C6 C5 C4 121.3(2) C6 C5 H5 119.3 C1 C6 H6 119.1 C5 C6 C1 121.8(2) C5 C6 H6 119.1 O1 C7 C2 112.90(17) O2 C7 O1 122.53(19) O2 C7 C2 124.5(2) N1 C8 H8 108.5 N1 C8 C9 112.12(18) N1 C8 C21 110.13(18) C9 C8 H8 108.5 C9 C8 C21 108.97(18) C21 C8 H8 108.5 C8 C9 H9 117.2 C10 C9 C8 125.7(3) C10 C9 H9 117.2 C9 C10 H10A 120.0 C9 C10 H10B 120.0 H10A C10 H10B 120.0 N2 C11 C12 122.5(2) N2 C11 C16 119.9(2) C16 C11 C12 117.54(19) C11 C12 C17 121.04(18) C13 C12 C11 119.78(19) C13 C12 C17 119.16(19) C12 C13 H13 119.6 C14 C13 C12 120.8(2) C14 C13 H13 119.6 O6 C14 C13 124.6(2) O6 C14 C15 115.9(2) C13 C14 C15 119.4(2) C14 C15 H15 119.6 C16 C15 C14 120.8(2) C16 C15 H15 119.6 C11 C16 H16 119.2 C15 C16 C11 121.5(2) C15 C16 H16 119.2 O3 C17 C12 112.92(17) O4 C17 O3 122.61(19) O4 C17 C12 124.46(19) N2 C18 H18 107.0 N2 C18 C19 115.1(2) N2 C18 C22 109.91(19) C19 C18 H18 107.0 C19 C18 C22 110.40(19) C22 C18 H18 107.0 C18 C19 H19 116.5 C20 C19 C18 127.0(3) C20 C19 H19 116.5 C19 C20 H20A 120.0 C19 C20 H20B 120.0 H20A C20 H20B 120.0 O3 C21 C8 110.32(16) O3 C21 H21A 109.6 O3 C21 H21B 109.6 C8 C21 H21A 109.6 C8 C21 H21B 109.6 H21A C21 H21B 108.1 O1 C22 C18 109.92(17) O1 C22 H22A 109.7 O1 C22 H22B 109.7 C18 C22 H22A 109.7 C18 C22 H22B 109.7 H22A C22 H22B 108.2 O5 C23 H23A 109.5 O5 C23 H23B 109.5 O5 C23 H23C 109.5 H23A C23 H23B 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 O6 C24 H24A 109.5 O6 C24 H24B 109.5 O6 C24 H24C 109.5 H24A C24 H24B 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C7 1.350(3) O1 C22 1.456(2) O2 C7 1.214(2) O3 C17 1.347(2) O3 C21 1.453(2) O4 C17 1.218(2) O5 C4 1.380(2) O5 C23 1.381(4) O6 C14 1.374(3) O6 C24 1.385(3) N1 C1 1.373(3) N1 C8 1.454(3) N1 H1 0.82(2) N2 C11 1.380(3) N2 C18 1.456(3) N2 H2 0.84(2) C1 C2 1.413(3) C1 C6 1.409(3) C2 C3 1.407(3) C2 C7 1.477(3) C3 H3 0.9300 C3 C4 1.380(3) C4 C5 1.379(3) C5 H5 0.9300 C5 C6 1.365(3) C6 H6 0.9300 C8 H8 0.9800 C8 C9 1.507(3) C8 C21 1.528(3) C9 H9 0.9300 C9 C10 1.276(4) C10 H10A 0.9300 C10 H10B 0.9300 C11 C12 1.416(3) C11 C16 1.405(3) C12 C13 1.404(3) C12 C17 1.470(3) C13 H13 0.9300 C13 C14 1.376(3) C14 C15 1.387(3) C15 H15 0.9300 C15 C16 1.368(3) C16 H16 0.9300 C18 H18 0.9800 C18 C19 1.507(3) C18 C22 1.523(3) C19 H19 0.9300 C19 C20 1.253(4) C20 H20A 0.9300 C20 H20B 0.9300 C21 H21A 0.9700 C21 H21B 0.9700 C22 H22A 0.9700 C22 H22B 0.9700 C23 H23A 0.9600 C23 H23B 0.9600 C23 H23C 0.9600 C24 H24A 0.9600 C24 H24B 0.9600 C24 H24C 0.9600