#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:06:36 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247601 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/57/7125703.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_7125703 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 'C22 H22 N2 O4' _chemical_formula_sum 'C22 H22 N2 O4' _chemical_formula_weight 378.41 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _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 102.505(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.7113(9) _cell_length_b 9.7397(5) _cell_length_c 14.7226(8) _cell_measurement_reflns_used 1701 _cell_measurement_temperature 293.1(2) _cell_measurement_theta_max 25.8460 _cell_measurement_theta_min 4.4520 _cell_volume 1919.5(2) _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 0.833 _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 -38.00 25.00 1.00 7.50 -- 15.49 -38.00 30.00 63 2 \w -14.00 59.00 1.00 7.50 -- 15.49 19.00 -90.00 73 3 \w -36.00 -9.00 1.00 7.50 -- 15.49 -57.00 -90.00 27 4 \w 37.00 82.00 1.00 7.50 -- 15.49 178.00-150.00 45 ; _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 -0.0206557000 _diffrn_orient_matrix_UB_12 -0.0516707000 _diffrn_orient_matrix_UB_13 -0.0324728000 _diffrn_orient_matrix_UB_21 0.0479229000 _diffrn_orient_matrix_UB_22 -0.0127100000 _diffrn_orient_matrix_UB_23 -0.0090568000 _diffrn_orient_matrix_UB_31 0.0092259000 _diffrn_orient_matrix_UB_32 -0.0497067000 _diffrn_orient_matrix_UB_33 0.0360569000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_unetI/netI 0.0600 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.833 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 8543 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.833 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.326 _diffrn_reflns_theta_min 3.523 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83895 _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 1.309 _exptl_crystal_description plate _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.211 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 261 _refine_ls_number_reflns 4391 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.1199 _refine_ls_R_factor_gt 0.0629 _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^)+(0.0580P)^2^+0.1125P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1194 _refine_ls_wR_factor_ref 0.1471 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2512 _reflns_number_total 4391 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc07372h2.cif _cod_data_source_block syn-3a _cod_depositor_comments 'Adding full bibliography for 7125703--7125707.cif.' _cod_database_code 7125703 _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 99.66 _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 2.a Ternary CH refined with riding coordinates: C21(H21), C18(H18) 2.b Secondary CH2 refined with riding coordinates: C00I(H00A,H00B), C22(H22A,H22B) 2.c Aromatic/amide H refined with riding coordinates: C6(H6), C3(H3), C5(H5), C13(H13), C16(H16), C4(H4), C9(H9), C19(H19), C14(H14), C15(H15) 2.d X=CH2 refined with riding coordinates: C20(H20A,H20B), C10(H10A,H10B) ; _shelx_res_file ; TITL exp_6063_a.res in P2(1)/n syn-3a.res created by SHELXL-2018/1 at 14:40:29 on 02-Nov-2019 REM Old TITL exp_6063 in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.191, Rweak 0.566, Alpha 0.029, Orientation as input REM Formula found by SHELXT: C21 N2 O5 CELL 0.71073 13.7113 9.7397 14.7226 90 102.505 90 ZERR 4 0.0009 0.0005 0.0008 0 0.006 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 88 88 8 16 L.S. 10 PLAN 2 TEMP 20.0(2) BOND $H list 4 fmap 2 acta REM REM REM WGHT 0.058000 0.112500 FVAR 0.66176 O1 4 0.721071 0.781118 0.390226 11.00000 0.05551 0.04844 = 0.04012 0.00225 0.00513 0.00603 O3 4 0.792657 0.296744 0.582762 11.00000 0.04684 0.05120 = 0.04756 0.00703 -0.00184 -0.00218 O2 4 0.859481 0.651124 0.425448 11.00000 0.05860 0.05807 = 0.04529 0.00150 0.01773 0.01185 O4 4 0.818861 0.354386 0.442342 11.00000 0.04735 0.06431 = 0.05003 -0.00008 0.01210 0.00794 N1 3 0.885614 0.559907 0.604107 11.00000 0.06321 0.04553 = 0.03644 0.00059 0.01392 0.01073 N2 3 0.659934 0.498278 0.340093 11.00000 0.04205 0.04825 = 0.05119 0.00780 0.00640 0.00435 C12 1 0.651888 0.334561 0.463048 11.00000 0.04203 0.03931 = 0.03941 -0.00824 0.00472 -0.00054 C1 1 0.850131 0.686578 0.620260 11.00000 0.03360 0.03950 = 0.04311 -0.00326 0.00835 -0.00368 C2 1 0.808147 0.774968 0.545998 11.00000 0.03855 0.04006 = 0.03928 -0.00061 0.01019 -0.00194 C21 1 0.914170 0.452336 0.672402 11.00000 0.04308 0.04609 = 0.04040 0.00259 0.00619 0.00261 AFIX 13 H21 2 0.870583 0.458165 0.716955 11.00000 -1.20000 AFIX 0 C11 1 0.605366 0.419224 0.387752 11.00000 0.04212 0.03989 = 0.04146 -0.00678 0.00431 0.00151 C6 1 0.850645 0.731260 0.710706 11.00000 0.04172 0.04597 = 0.03944 -0.00138 0.00723 -0.00177 AFIX 43 H6 2 0.876865 0.674642 0.760926 11.00000 -1.20000 AFIX 0 C17 1 0.761446 0.329645 0.491721 11.00000 0.04790 0.03233 = 0.04022 -0.00425 0.00355 0.00383 C7 1 0.801211 0.729614 0.449702 11.00000 0.04730 0.03754 = 0.04306 0.00512 0.01302 -0.00168 C3 1 0.771364 0.902922 0.564627 11.00000 0.05235 0.04165 = 0.04998 0.00124 0.00928 0.00343 AFIX 43 H3 2 0.743985 0.960676 0.515394 11.00000 -1.20000 AFIX 0 C5 1 0.812970 0.857509 0.726250 11.00000 0.04842 0.05383 = 0.04622 -0.01176 0.01505 -0.00405 AFIX 43 H5 2 0.813238 0.884479 0.786900 11.00000 -1.20000 AFIX 0 C18 1 0.620954 0.617705 0.284700 11.00000 0.04763 0.05000 = 0.04088 0.00327 0.00517 0.00729 AFIX 13 H18 2 0.565215 0.653805 0.309407 11.00000 -1.20000 AFIX 0 C00I 1 0.897557 0.313776 0.624491 11.00000 0.04635 0.04636 = 0.05236 0.00408 -0.00504 0.00737 AFIX 23 H00A 2 0.936446 0.307880 0.576876 11.00000 -1.20000 H00B 2 0.919406 0.241212 0.669415 11.00000 -1.20000 AFIX 0 C13 1 0.592954 0.260022 0.511774 11.00000 0.05664 0.04873 = 0.04386 -0.00184 0.00852 -0.00614 AFIX 43 H13 2 0.623788 0.205331 0.561526 11.00000 -1.20000 AFIX 0 C16 1 0.500693 0.420889 0.365036 11.00000 0.04278 0.05524 = 0.05663 0.00107 0.00116 0.00238 AFIX 43 H16 2 0.468243 0.473970 0.315058 11.00000 -1.20000 AFIX 0 C22 1 0.699902 0.729055 0.295623 11.00000 0.06398 0.05418 = 0.03566 0.00557 0.00721 0.00236 AFIX 23 H22A 2 0.760483 0.692049 0.281239 11.00000 -1.20000 H22B 2 0.676496 0.803320 0.252508 11.00000 -1.20000 AFIX 0 C4 1 0.774696 0.945260 0.653719 11.00000 0.05930 0.04072 = 0.05856 -0.00669 0.01556 0.00849 AFIX 43 H4 2 0.751530 1.031867 0.665289 11.00000 -1.20000 AFIX 0 C9 1 1.020378 0.466103 0.725343 11.00000 0.04993 0.05538 = 0.05654 -0.00006 0.00215 0.00072 AFIX 43 H9 2 1.069035 0.479173 0.690901 11.00000 -1.20000 AFIX 0 C19 1 0.582249 0.589062 0.183265 11.00000 0.06405 0.06398 = 0.04859 0.00108 0.00178 0.00697 AFIX 43 H19 2 0.558867 0.663544 0.145228 11.00000 -1.20000 AFIX 0 C14 1 0.490315 0.265465 0.488006 11.00000 0.05662 0.06546 = 0.06071 -0.00651 0.01824 -0.01291 AFIX 43 H14 2 0.452028 0.215133 0.521147 11.00000 -1.20000 AFIX 0 C15 1 0.445069 0.347101 0.413959 11.00000 0.04144 0.07061 = 0.07047 -0.00839 0.00985 -0.00272 AFIX 43 H15 2 0.375734 0.351672 0.397351 11.00000 -1.20000 AFIX 0 C20 1 0.578579 0.471484 0.144562 11.00000 0.08961 0.08701 = 0.06085 -0.01421 0.00844 0.00953 AFIX 93 H20A 2 0.601187 0.394201 0.180005 11.00000 -1.20000 H20B 2 0.553295 0.463019 0.080894 11.00000 -1.20000 AFIX 0 C10 1 1.049735 0.461288 0.814779 11.00000 0.07995 0.08584 = 0.06962 0.01752 -0.01808 -0.02032 AFIX 93 H10A 2 1.003429 0.448365 0.851751 11.00000 -1.20000 H10B 2 1.117177 0.470744 0.842200 11.00000 -1.20000 AFIX 0 H1 2 0.893759 0.546143 0.552999 11.00000 0.03529 H2 2 0.726474 0.488553 0.354980 11.00000 0.06421 HKLF 4 REM exp_6063_a.res in P2(1)/n REM R1 = 0.0629 for 2512 Fo > 4sig(Fo) and 0.1199 for all 4391 data REM 261 parameters refined using 0 restraints END WGHT 0.0580 0.1125 REM Highest difference peak 0.211, deepest hole -0.224, 1-sigma level 0.049 Q1 1 0.9635 0.5943 0.5143 11.00000 0.05 0.21 Q2 1 0.5316 0.8463 0.0730 11.00000 0.05 0.17 ; _shelx_res_checksum 9097 _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 1.217 _oxdiff_exptl_absorpt_empirical_full_min 0.906 loop_ _space_group_symop_operation_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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn O1 O 0.72107(12) 0.78112(15) 0.39023(9) 0.0488(4) Uani 1 1 d . O3 O 0.79266(11) 0.29674(15) 0.58276(10) 0.0504(4) Uani 1 1 d . O2 O 0.85948(12) 0.65112(16) 0.42545(10) 0.0530(4) Uani 1 1 d . O4 O 0.81886(12) 0.35439(16) 0.44234(10) 0.0537(4) Uani 1 1 d . N1 N 0.88561(15) 0.55991(19) 0.60411(14) 0.0479(5) Uani 1 1 d . N2 N 0.65993(16) 0.4983(2) 0.34009(13) 0.0477(5) Uani 1 1 d . C12 C 0.65189(16) 0.3346(2) 0.46305(13) 0.0409(5) Uani 1 1 d . C1 C 0.85013(15) 0.6866(2) 0.62026(14) 0.0387(5) Uani 1 1 d . C2 C 0.80815(15) 0.7750(2) 0.54600(13) 0.0390(5) Uani 1 1 d . C21 C 0.91417(16) 0.4523(2) 0.67240(14) 0.0436(5) Uani 1 1 d . H21 H 0.870583 0.458165 0.716955 0.052 Uiso 1 1 calc R C11 C 0.60537(16) 0.4192(2) 0.38775(14) 0.0419(5) Uani 1 1 d . C6 C 0.85065(16) 0.7313(2) 0.71071(14) 0.0426(5) Uani 1 1 d . H6 H 0.876865 0.674642 0.760926 0.051 Uiso 1 1 calc R C17 C 0.76145(17) 0.3296(2) 0.49172(14) 0.0411(5) Uani 1 1 d . C7 C 0.80121(17) 0.7296(2) 0.44970(14) 0.0421(5) Uani 1 1 d . C3 C 0.77136(17) 0.9029(2) 0.56463(15) 0.0483(6) Uani 1 1 d . H3 H 0.743985 0.960676 0.515394 0.058 Uiso 1 1 calc R C5 C 0.81297(17) 0.8575(2) 0.72625(15) 0.0488(6) Uani 1 1 d . H5 H 0.813238 0.884479 0.786900 0.059 Uiso 1 1 calc R C18 C 0.62095(17) 0.6177(2) 0.28470(14) 0.0468(6) Uani 1 1 d . H18 H 0.565215 0.653805 0.309407 0.056 Uiso 1 1 calc R C00I C 0.89756(17) 0.3138(2) 0.62449(16) 0.0507(6) Uani 1 1 d . H00A H 0.936446 0.307880 0.576876 0.061 Uiso 1 1 calc R H00B H 0.919406 0.241212 0.669415 0.061 Uiso 1 1 calc R C13 C 0.59295(19) 0.2600(2) 0.51177(15) 0.0501(6) Uani 1 1 d . H13 H 0.623788 0.205331 0.561526 0.060 Uiso 1 1 calc R C16 C 0.50069(18) 0.4209(2) 0.36504(16) 0.0530(6) Uani 1 1 d . H16 H 0.468243 0.473970 0.315058 0.064 Uiso 1 1 calc R C22 C 0.69990(19) 0.7291(2) 0.29562(13) 0.0518(6) Uani 1 1 d . H22A H 0.760483 0.692049 0.281239 0.062 Uiso 1 1 calc R H22B H 0.676496 0.803320 0.252508 0.062 Uiso 1 1 calc R C4 C 0.77470(18) 0.9453(2) 0.65372(16) 0.0524(6) Uani 1 1 d . H4 H 0.751530 1.031867 0.665289 0.063 Uiso 1 1 calc R C9 C 1.02038(19) 0.4661(2) 0.72534(16) 0.0554(6) Uani 1 1 d . H9 H 1.069035 0.479173 0.690901 0.066 Uiso 1 1 calc R C19 C 0.58225(19) 0.5891(3) 0.18327(16) 0.0605(7) Uani 1 1 d . H19 H 0.558867 0.663544 0.145228 0.073 Uiso 1 1 calc R C14 C 0.4903(2) 0.2655(3) 0.48801(17) 0.0601(7) Uani 1 1 d . H14 H 0.452028 0.215133 0.521147 0.072 Uiso 1 1 calc R C15 C 0.44507(19) 0.3471(3) 0.41396(17) 0.0612(7) Uani 1 1 d . H15 H 0.375734 0.351672 0.397351 0.073 Uiso 1 1 calc R C20 C 0.5786(2) 0.4715(3) 0.14456(19) 0.0803(9) Uani 1 1 d . H20A H 0.601187 0.394201 0.180005 0.096 Uiso 1 1 calc R H20B H 0.553295 0.463019 0.080894 0.096 Uiso 1 1 calc R C10 C 1.0497(2) 0.4613(3) 0.81478(19) 0.0837(10) Uani 1 1 d . H10A H 1.003429 0.448365 0.851751 0.100 Uiso 1 1 calc R H10B H 1.117177 0.470744 0.842200 0.100 Uiso 1 1 calc R H1 H 0.8938(15) 0.546(2) 0.5530(14) 0.035(6) Uiso 1 1 d . H2 H 0.726(2) 0.489(3) 0.3550(16) 0.064(8) 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 0.0555(10) 0.0484(9) 0.0401(8) 0.0023(7) 0.0051(7) 0.0060(8) O3 0.0468(9) 0.0512(10) 0.0476(8) 0.0070(7) -0.0018(7) -0.0022(8) O2 0.0586(10) 0.0581(10) 0.0453(8) 0.0015(8) 0.0177(7) 0.0119(9) O4 0.0474(10) 0.0643(11) 0.0500(9) -0.0001(8) 0.0121(8) 0.0079(8) N1 0.0632(14) 0.0455(12) 0.0364(11) 0.0006(10) 0.0139(9) 0.0107(10) N2 0.0420(12) 0.0483(12) 0.0512(11) 0.0078(9) 0.0064(9) 0.0044(10) C12 0.0420(12) 0.0393(12) 0.0394(11) -0.0082(10) 0.0047(9) -0.0005(10) C1 0.0336(11) 0.0395(12) 0.0431(11) -0.0033(10) 0.0084(9) -0.0037(10) C2 0.0385(12) 0.0401(12) 0.0393(11) -0.0006(10) 0.0102(9) -0.0019(10) C21 0.0431(13) 0.0461(13) 0.0404(11) 0.0026(10) 0.0062(9) 0.0026(11) C11 0.0421(13) 0.0399(12) 0.0415(11) -0.0068(10) 0.0043(10) 0.0015(11) C6 0.0417(12) 0.0460(13) 0.0394(11) -0.0014(10) 0.0072(9) -0.0018(11) C17 0.0479(13) 0.0323(12) 0.0402(12) -0.0042(10) 0.0036(10) 0.0038(10) C7 0.0473(13) 0.0375(12) 0.0431(12) 0.0051(10) 0.0130(10) -0.0017(11) C3 0.0523(15) 0.0417(13) 0.0500(13) 0.0012(11) 0.0093(11) 0.0034(11) C5 0.0484(14) 0.0538(15) 0.0462(12) -0.0118(12) 0.0150(11) -0.0041(12) C18 0.0476(14) 0.0500(14) 0.0409(11) 0.0033(11) 0.0052(10) 0.0073(12) C00I 0.0464(14) 0.0464(13) 0.0524(13) 0.0041(11) -0.0050(10) 0.0074(12) C13 0.0566(16) 0.0487(14) 0.0439(12) -0.0018(11) 0.0085(11) -0.0061(12) C16 0.0428(14) 0.0552(15) 0.0566(14) 0.0011(12) 0.0012(11) 0.0024(12) C22 0.0640(16) 0.0542(14) 0.0357(11) 0.0056(11) 0.0072(10) 0.0024(13) C4 0.0593(16) 0.0407(13) 0.0586(14) -0.0067(12) 0.0156(12) 0.0085(12) C9 0.0499(15) 0.0554(15) 0.0565(14) -0.0001(12) 0.0022(11) 0.0007(12) C19 0.0641(17) 0.0640(17) 0.0486(14) 0.0011(13) 0.0018(12) 0.0070(14) C14 0.0566(17) 0.0655(17) 0.0607(15) -0.0065(13) 0.0182(13) -0.0129(14) C15 0.0414(14) 0.0706(17) 0.0705(16) -0.0084(15) 0.0098(12) -0.0027(14) C20 0.090(2) 0.087(2) 0.0609(16) -0.0142(16) 0.0084(16) 0.0095(18) C10 0.080(2) 0.086(2) 0.0696(18) 0.0175(16) -0.0181(15) -0.0203(18) 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 117.38(17) C17 O3 C00I 117.74(17) C1 N1 C21 125.90(19) C1 N1 H1 116.4(15) C21 N1 H1 117.6(15) C11 N2 C18 124.2(2) C11 N2 H2 117.1(16) C18 N2 H2 116.9(16) C11 C12 C17 120.1(2) C13 C12 C11 119.5(2) C13 C12 C17 120.3(2) N1 C1 C2 121.10(18) N1 C1 C6 121.20(19) C6 C1 C2 117.66(19) C1 C2 C7 119.63(19) C3 C2 C1 119.79(18) C3 C2 C7 120.56(19) N1 C21 H21 108.1 N1 C21 C00I 109.29(17) N1 C21 C9 112.48(19) C00I C21 H21 108.1 C9 C21 H21 108.1 C9 C21 C00I 110.61(18) N2 C11 C12 121.7(2) N2 C11 C16 121.1(2) C16 C11 C12 117.2(2) C1 C6 H6 119.6 C5 C6 C1 120.9(2) C5 C6 H6 119.6 O3 C17 C12 112.09(19) O4 C17 O3 122.4(2) O4 C17 C12 125.46(19) O1 C7 C2 112.92(19) O2 C7 O1 122.70(19) O2 C7 C2 124.4(2) C2 C3 H3 119.3 C4 C3 C2 121.4(2) C4 C3 H3 119.3 C6 C5 H5 119.3 C6 C5 C4 121.33(19) C4 C5 H5 119.3 N2 C18 H18 107.5 N2 C18 C22 110.21(18) N2 C18 C19 114.69(19) C22 C18 H18 107.5 C19 C18 H18 107.5 C19 C18 C22 109.24(19) O3 C00I C21 109.57(18) O3 C00I H00A 109.8 O3 C00I H00B 109.8 C21 C00I H00A 109.8 C21 C00I H00B 109.8 H00A C00I H00B 108.2 C12 C13 H13 119.2 C14 C13 C12 121.6(2) C14 C13 H13 119.2 C11 C16 H16 119.0 C15 C16 C11 122.0(2) C15 C16 H16 119.0 O1 C22 C18 109.97(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 C3 C4 C5 119.0(2) C3 C4 H4 120.5 C5 C4 H4 120.5 C21 C9 H9 117.3 C10 C9 C21 125.4(3) C10 C9 H9 117.3 C18 C19 H19 117.1 C20 C19 C18 125.7(2) C20 C19 H19 117.1 C13 C14 H14 120.6 C13 C14 C15 118.8(2) C15 C14 H14 120.6 C16 C15 C14 120.9(2) C16 C15 H15 119.6 C14 C15 H15 119.6 C19 C20 H20A 120.0 C19 C20 H20B 120.0 H20A C20 H20B 120.0 C9 C10 H10A 120.0 C9 C10 H10B 120.0 H10A C10 H10B 120.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C7 1.345(2) O1 C22 1.451(2) O3 C17 1.354(2) O3 C00I 1.446(2) O2 C7 1.214(2) O4 C17 1.206(2) N1 C1 1.366(3) N1 C21 1.446(3) N1 H1 0.80(2) N2 C11 1.368(3) N2 C18 1.454(3) N2 H2 0.90(3) C12 C11 1.418(3) C12 C17 1.471(3) C12 C13 1.395(3) C1 C2 1.413(3) C1 C6 1.399(3) C2 C7 1.468(3) C2 C3 1.394(3) C21 H21 0.9800 C21 C00I 1.517(3) C21 C9 1.502(3) C11 C16 1.401(3) C6 H6 0.9300 C6 C5 1.372(3) C3 H3 0.9300 C3 C4 1.366(3) C5 H5 0.9300 C5 C4 1.380(3) C18 H18 0.9800 C18 C22 1.516(3) C18 C19 1.499(3) C00I H00A 0.9700 C00I H00B 0.9700 C13 H13 0.9300 C13 C14 1.376(3) C16 H16 0.9300 C16 C15 1.362(3) C22 H22A 0.9700 C22 H22B 0.9700 C4 H4 0.9300 C9 H9 0.9300 C9 C10 1.292(3) C19 H19 0.9300 C19 C20 1.275(3) C14 H14 0.9300 C14 C15 1.383(3) C15 H15 0.9300 C20 H20A 0.9300 C20 H20B 0.9300 C10 H10A 0.9300 C10 H10B 0.9300