#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:06:36 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247601 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/57/7125707.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_7125707 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 '2(C11 H11 N O2)' _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 99.915(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.5996(10) _cell_length_b 8.1161(5) _cell_length_c 16.4481(14) _cell_measurement_reflns_used 2229 _cell_measurement_temperature 293.1(2) _cell_measurement_theta_max 25.1780 _cell_measurement_theta_min 3.7760 _cell_volume 1919.9(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 0.997 _diffrn_measured_fraction_theta_max 0.855 _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 -51.00 -20.00 1.00 7.50 -- -16.12 -57.00 -30.00 31 2 \w -84.00 52.00 1.00 7.50 -- -16.12 0.00 0.00 136 3 \w -10.00 36.00 1.00 7.50 -- 15.49 -77.00 150.00 46 4 \w 11.00 51.00 1.00 7.50 -- -16.12 57.00-180.00 40 ; _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 0.0064892000 _diffrn_orient_matrix_UB_12 0.0143595000 _diffrn_orient_matrix_UB_13 0.0431566000 _diffrn_orient_matrix_UB_21 -0.0413373000 _diffrn_orient_matrix_UB_22 -0.0444118000 _diffrn_orient_matrix_UB_23 0.0022615000 _diffrn_orient_matrix_UB_31 0.0261086000 _diffrn_orient_matrix_UB_32 -0.0738517000 _diffrn_orient_matrix_UB_33 0.0070485000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_unetI/netI 0.0686 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.855 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 10170 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.855 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.332 _diffrn_reflns_theta_min 3.449 _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 0.43188 _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 prism _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.32 _refine_diff_density_max 0.207 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 280 _refine_ls_number_reflns 4506 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 0.992 _refine_ls_R_factor_all 0.1374 _refine_ls_R_factor_gt 0.0564 _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^)+(0.0508P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1107 _refine_ls_wR_factor_ref 0.1421 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2192 _reflns_number_total 4506 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc07372h2.cif _cod_data_source_block anti-3a _cod_depositor_comments 'Adding full bibliography for 7125703--7125707.cif.' _cod_database_code 7125707 _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 99.60 _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. Restrained distances C21B-C20B \\sim C21-C20 with sigma of 0.01 C20-C19 \\sim C20B-C19 with sigma of 0.01 3. Others Sof(H19A)=Sof(C20B)=Sof(H20B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=1-FVAR(1) Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21A)=Sof(H21B)=FVAR(1) 4.a Ternary CH refined with riding coordinates: C8(H8), C19(H19), C19(H19A) 4.b Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C22(H22A,H22B) 4.c Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C20B(H20B) 4.d X=CH2 refined with riding coordinates: C10(H10A,H10B), C21(H21A,H21B), C21B(H21C,H21D) ; _shelx_res_file ; TITL exp_6064_a.res in P2(1)/n anti-3a.res created by SHELXL-2018/1 at 14:32:54 on 02-Nov-2019 REM Old TITL exp_6064 in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.223, Rweak 0.426, Alpha 0.038, Orientation as input REM Formula found by SHELXT: C20 N2 O6 CELL 0.71073 14.5996 8.1161 16.4481 90 99.915 90 ZERR 4 0.001 0.0005 0.0014 0 0.007 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 88 88 8 16 SADI 0.01 C21B C20B C21 C20 SADI 0.01 C20 C19 C20B C19 L.S. 10 PLAN 4 TEMP 20.0(2) BOND $H list 4 fmap 2 acta REM REM REM WGHT 0.050800 FVAR 0.45835 0.64920 O1 4 0.668499 0.551679 0.479772 11.00000 0.04432 0.05583 = 0.05136 0.00552 0.00119 -0.00418 O2 4 0.546364 0.409140 0.414614 11.00000 0.05624 0.03856 = 0.08523 -0.00601 -0.00145 -0.00009 N1 3 0.387221 0.586559 0.372666 11.00000 0.04118 0.04617 = 0.05972 0.00349 0.00962 0.00281 H1 2 0.415123 0.500461 0.386050 11.00000 0.04106 C1 1 0.445554 0.721877 0.386619 11.00000 0.05421 0.04055 = 0.03689 0.00296 0.00894 0.00020 C2 1 0.542588 0.702761 0.411423 11.00000 0.05114 0.03516 = 0.03743 0.00341 0.01029 -0.00261 C3 1 0.599952 0.842178 0.420164 11.00000 0.06532 0.04998 = 0.04461 0.00019 0.01065 -0.01500 AFIX 43 H3 2 0.663788 0.829128 0.436250 11.00000 -1.20000 AFIX 0 C4 1 0.564123 0.996897 0.405564 11.00000 0.10112 0.04511 = 0.05510 0.00046 0.01395 -0.01603 AFIX 43 H4 2 0.603118 1.088252 0.409956 11.00000 -1.20000 AFIX 0 C5 1 0.469507 1.015268 0.384281 11.00000 0.11812 0.03398 = 0.06108 0.00646 0.01680 0.00738 AFIX 43 H5 2 0.444556 1.120634 0.376244 11.00000 -1.20000 AFIX 0 C6 1 0.410993 0.881984 0.374608 11.00000 0.07404 0.05100 = 0.05440 0.00865 0.00904 0.01257 AFIX 43 H6 2 0.347263 0.898490 0.359810 11.00000 -1.20000 AFIX 0 C7 1 0.583424 0.540717 0.433490 11.00000 0.04138 0.04571 = 0.04510 -0.00165 0.01105 -0.00445 C8 1 0.292698 0.586152 0.389552 11.00000 0.04159 0.06631 = 0.05370 0.01043 0.00443 0.00876 AFIX 13 H8 2 0.260993 0.683670 0.363119 11.00000 -1.20000 AFIX 0 C9 1 0.241118 0.436902 0.352186 11.00000 0.04487 0.11228 = 0.05364 -0.00274 0.00311 -0.01726 AFIX 43 H9 2 0.180448 0.425687 0.361681 11.00000 -1.20000 AFIX 0 C10 1 0.269989 0.322516 0.308731 11.00000 0.08174 0.09204 = 0.06372 -0.00258 0.00311 -0.03880 AFIX 93 H10A 2 0.330048 0.326597 0.297048 11.00000 -1.20000 H10B 2 0.230806 0.235724 0.288992 11.00000 -1.20000 AFIX 0 C11 1 0.711263 0.404701 0.518762 11.00000 0.04636 0.06237 = 0.06276 0.00250 0.01094 0.01325 AFIX 23 H11A 2 0.775365 0.397331 0.510578 11.00000 -1.20000 H11B 2 0.678339 0.307763 0.494726 11.00000 -1.20000 AFIX 0 O3 4 0.429313 0.192953 -0.115915 11.00000 0.06739 0.07544 = 0.05052 -0.00051 0.00194 0.01024 O4 4 0.567255 0.115394 -0.043762 11.00000 0.04874 0.07516 = 0.05781 -0.00367 0.01590 0.00399 N2 3 0.589689 0.161322 0.120993 11.00000 0.05402 0.07913 = 0.05001 -0.00893 0.00790 0.00818 H2 2 0.608708 0.122164 0.081978 11.00000 0.04592 C12 1 0.512593 0.257941 0.103424 11.00000 0.04329 0.05236 = 0.06201 -0.00550 0.01562 -0.00736 C13 1 0.466098 0.281629 0.021508 11.00000 0.04444 0.04674 = 0.05973 -0.00313 0.01376 -0.01081 C14 1 0.391615 0.393241 0.005786 11.00000 0.05485 0.04872 = 0.07526 0.00731 0.01389 -0.00412 AFIX 43 H14 2 0.361631 0.409355 -0.048257 11.00000 -1.20000 AFIX 0 C15 1 0.361994 0.479331 0.068586 11.00000 0.06297 0.05425 = 0.09416 0.00226 0.03173 0.00360 AFIX 43 H15 2 0.313217 0.554143 0.057219 11.00000 -1.20000 AFIX 0 C16 1 0.405609 0.452829 0.147996 11.00000 0.07803 0.06308 = 0.08958 -0.01184 0.03889 0.00129 AFIX 43 H16 2 0.385596 0.509947 0.190724 11.00000 -1.20000 AFIX 0 C17 1 0.478353 0.343732 0.166164 11.00000 0.07034 0.06905 = 0.06302 -0.00783 0.02052 -0.00261 AFIX 43 H17 2 0.505385 0.326391 0.220942 11.00000 -1.20000 AFIX 0 C18 1 0.494557 0.190223 -0.047143 11.00000 0.04835 0.05480 = 0.05249 0.00189 0.01238 -0.00572 C19 1 0.611815 0.057559 0.194099 11.00000 0.07165 0.08936 = 0.05141 -0.01290 -0.00553 0.01346 PART 1 AFIX 13 H19 2 0.599248 0.120065 0.241957 21.00000 -1.20000 AFIX 13 PART 0 PART 2 H19A 2 0.591082 0.120772 0.238347 -21.00000 -1.20000 AFIX 0 PART 0 C22 1 0.446428 0.098318 -0.186511 11.00000 0.08160 0.09482 = 0.04641 0.00419 0.00882 0.00833 AFIX 23 H22A 2 0.511828 0.069892 -0.179854 11.00000 -1.20000 H22B 2 0.430574 0.163694 -0.236317 11.00000 -1.20000 AFIX 0 PART 1 C20 1 0.716431 0.030096 0.203396 21.00000 0.05572 0.10931 = 0.05771 0.02280 -0.00645 0.00685 AFIX 43 H20 2 0.738044 0.003800 0.155013 21.00000 -1.20000 AFIX 0 C21 1 0.776820 0.037875 0.266408 21.00000 0.06981 0.15826 = 0.10142 0.01511 -0.01817 -0.00913 AFIX 93 H21A 2 0.760094 0.063604 0.316973 21.00000 -1.20000 H21B 2 0.838791 0.017973 0.263053 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C20B 1 0.706628 -0.007054 0.231601 -21.00000 0.10307 0.07834 = 0.05402 0.02210 -0.00554 -0.03050 AFIX 43 H20B 2 0.716599 -0.089509 0.271407 -21.00000 -1.20000 AFIX 0 C21B 1 0.769133 0.062217 0.203300 -21.00000 0.07438 0.19054 = 0.06533 0.01078 0.02116 0.01532 AFIX 93 H21C 2 0.754742 0.143943 0.163519 -21.00000 -1.20000 H21D 2 0.830801 0.032887 0.221675 -21.00000 -1.20000 AFIX 0 HKLF 4 REM exp_6064_a.res in P2(1)/n REM R1 = 0.0564 for 2192 Fo > 4sig(Fo) and 0.1374 for all 4506 data REM 280 parameters refined using 2 restraints END WGHT 0.0508 0.0000 REM Highest difference peak 0.207, deepest hole -0.158, 1-sigma level 0.037 Q1 1 0.4328 0.1136 0.0397 11.00000 0.05 0.21 Q2 1 0.5017 0.3242 -0.1571 11.00000 0.05 0.15 Q3 1 0.4984 0.1780 0.0542 11.00000 0.05 0.15 Q4 1 0.4781 0.6455 0.1574 11.00000 0.05 0.15 ; _shelx_res_checksum 96324 _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 2.216 _oxdiff_exptl_absorpt_empirical_full_min 0.562 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.66850(10) 0.55168(18) 0.47977(9) 0.0513(4) Uani 1 1 d . . . . O2 O 0.54636(10) 0.40914(19) 0.41461(10) 0.0616(5) Uani 1 1 d . . . . N1 N 0.38722(13) 0.5866(3) 0.37267(12) 0.0489(5) Uani 1 1 d . . . . H1 H 0.4151(14) 0.500(2) 0.3860(12) 0.041(7) Uiso 1 1 d . . . . C1 C 0.44555(15) 0.7219(3) 0.38662(12) 0.0438(5) Uani 1 1 d . . . . C2 C 0.54259(14) 0.7028(2) 0.41142(12) 0.0409(5) Uani 1 1 d . . . . C3 C 0.59995(16) 0.8422(3) 0.42016(13) 0.0532(6) Uani 1 1 d . . . . H3 H 0.663788 0.829128 0.436250 0.064 Uiso 1 1 calc R . . . C4 C 0.5641(2) 0.9969(3) 0.40556(15) 0.0670(7) Uani 1 1 d . . . . H4 H 0.603118 1.088252 0.409956 0.080 Uiso 1 1 calc R . . . C5 C 0.4695(2) 1.0153(3) 0.38428(15) 0.0709(8) Uani 1 1 d . . . . H5 H 0.444556 1.120634 0.376244 0.085 Uiso 1 1 calc R . . . C6 C 0.41099(18) 0.8820(3) 0.37461(14) 0.0601(7) Uani 1 1 d . . . . H6 H 0.347263 0.898490 0.359810 0.072 Uiso 1 1 calc R . . . C7 C 0.58342(15) 0.5407(3) 0.43349(13) 0.0436(5) Uani 1 1 d . . . . C8 C 0.29270(15) 0.5862(3) 0.38955(14) 0.0543(6) Uani 1 1 d . . . . H8 H 0.260993 0.683670 0.363119 0.065 Uiso 1 1 calc R . . . C9 C 0.24112(17) 0.4369(4) 0.35219(15) 0.0709(8) Uani 1 1 d . . . . H9 H 0.180448 0.425687 0.361681 0.085 Uiso 1 1 calc R . . . C10 C 0.2700(2) 0.3225(4) 0.30873(17) 0.0803(8) Uani 1 1 d . . . . H10A H 0.330048 0.326597 0.297048 0.096 Uiso 1 1 calc R . . . H10B H 0.230806 0.235724 0.288992 0.096 Uiso 1 1 calc R . . . C11 C 0.71126(15) 0.4047(3) 0.51876(15) 0.0570(6) Uani 1 1 d . . . . H11A H 0.775365 0.397331 0.510578 0.068 Uiso 1 1 calc R . . . H11B H 0.678339 0.307763 0.494726 0.068 Uiso 1 1 calc R . . . O3 O 0.42931(11) 0.1930(2) -0.11592(9) 0.0654(5) Uani 1 1 d . . . . O4 O 0.56726(11) 0.1154(2) -0.04376(9) 0.0598(5) Uani 1 1 d . . . . N2 N 0.58969(14) 0.1613(3) 0.12099(13) 0.0612(6) Uani 1 1 d . . . . H2 H 0.6087(14) 0.122(3) 0.0820(13) 0.046(7) Uiso 1 1 d . . . . C12 C 0.51259(15) 0.2579(3) 0.10342(14) 0.0518(6) Uani 1 1 d . . . . C13 C 0.46610(15) 0.2816(3) 0.02151(14) 0.0497(6) Uani 1 1 d . . . . C14 C 0.39161(16) 0.3932(3) 0.00579(16) 0.0593(7) Uani 1 1 d . . . . H14 H 0.361631 0.409355 -0.048257 0.071 Uiso 1 1 calc R . . . C15 C 0.36199(18) 0.4793(3) 0.06859(19) 0.0683(7) Uani 1 1 d . . . . H15 H 0.313217 0.554143 0.057219 0.082 Uiso 1 1 calc R . . . C16 C 0.4056(2) 0.4528(3) 0.1480(2) 0.0740(8) Uani 1 1 d . . . . H16 H 0.385596 0.509947 0.190724 0.089 Uiso 1 1 calc R . . . C17 C 0.47835(18) 0.3437(3) 0.16616(16) 0.0664(7) Uani 1 1 d . . . . H17 H 0.505385 0.326391 0.220942 0.080 Uiso 1 1 calc R . . . C18 C 0.49456(16) 0.1902(3) -0.04714(14) 0.0514(6) Uani 1 1 d . . . . C19 C 0.61181(19) 0.0576(4) 0.19410(16) 0.0727(8) Uani 1 1 d D . . . H19 H 0.599248 0.120065 0.241957 0.087 Uiso 0.649(10) 1 calc R P A 1 H19A H 0.591082 0.120772 0.238347 0.087 Uiso 0.351(10) 1 calc R P A 2 C22 C 0.44643(19) 0.0983(4) -0.18651(15) 0.0745(8) Uani 1 1 d . . . . H22A H 0.511828 0.069892 -0.179854 0.089 Uiso 1 1 calc R . . . H22B H 0.430574 0.163694 -0.236317 0.089 Uiso 1 1 calc R . . . C20 C 0.7164(4) 0.0301(13) 0.2034(5) 0.076(3) Uani 0.649(10) 1 d D P A 1 H20 H 0.738044 0.003800 0.155013 0.091 Uiso 0.649(10) 1 calc R P A 1 C21 C 0.7768(4) 0.0379(8) 0.2664(5) 0.114(3) Uani 0.649(10) 1 d D P A 1 H21A H 0.760094 0.063604 0.316973 0.136 Uiso 0.649(10) 1 calc R P A 1 H21B H 0.838791 0.017973 0.263053 0.136 Uiso 0.649(10) 1 calc R P A 1 C20B C 0.7066(6) -0.0071(18) 0.2316(8) 0.081(5) Uani 0.351(10) 1 d D P A 2 H20B H 0.716599 -0.089509 0.271407 0.097 Uiso 0.351(10) 1 calc R P A 2 C21B C 0.7691(11) 0.062(2) 0.2033(9) 0.109(5) Uani 0.351(10) 1 d D P A 2 H21C H 0.754742 0.143943 0.163519 0.131 Uiso 0.351(10) 1 calc R P A 2 H21D H 0.830801 0.032887 0.221675 0.131 Uiso 0.351(10) 1 calc R P A 2 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 0.0443(9) 0.0558(10) 0.0514(9) 0.0055(8) 0.0012(7) -0.0042(7) O2 0.0562(10) 0.0386(9) 0.0852(12) -0.0060(8) -0.0015(8) -0.0001(8) N1 0.0412(12) 0.0462(12) 0.0597(12) 0.0035(10) 0.0096(9) 0.0028(11) C1 0.0542(14) 0.0406(13) 0.0369(11) 0.0030(10) 0.0089(10) 0.0002(12) C2 0.0511(13) 0.0352(12) 0.0374(11) 0.0034(10) 0.0103(9) -0.0026(11) C3 0.0653(15) 0.0500(15) 0.0446(12) 0.0002(11) 0.0106(11) -0.0150(13) C4 0.101(2) 0.0451(16) 0.0551(15) 0.0005(13) 0.0140(15) -0.0160(16) C5 0.118(3) 0.0340(14) 0.0611(17) 0.0065(12) 0.0168(17) 0.0074(17) C6 0.0740(17) 0.0510(15) 0.0544(14) 0.0087(12) 0.0090(12) 0.0126(14) C7 0.0414(13) 0.0457(14) 0.0451(12) -0.0016(11) 0.0110(10) -0.0044(11) C8 0.0416(13) 0.0663(16) 0.0537(14) 0.0104(13) 0.0044(11) 0.0088(12) C9 0.0449(15) 0.112(2) 0.0536(15) -0.0027(17) 0.0031(12) -0.0173(15) C10 0.082(2) 0.092(2) 0.0637(17) -0.0026(17) 0.0031(14) -0.0388(18) C11 0.0464(13) 0.0624(15) 0.0628(15) 0.0025(13) 0.0109(11) 0.0132(12) O3 0.0674(11) 0.0754(12) 0.0505(9) -0.0005(9) 0.0019(8) 0.0102(9) O4 0.0487(10) 0.0752(12) 0.0578(10) -0.0037(9) 0.0159(8) 0.0040(9) N2 0.0540(13) 0.0791(16) 0.0500(12) -0.0089(12) 0.0079(10) 0.0082(12) C12 0.0433(14) 0.0524(14) 0.0620(15) -0.0055(13) 0.0156(11) -0.0074(12) C13 0.0444(13) 0.0467(13) 0.0597(14) -0.0031(12) 0.0138(11) -0.0108(11) C14 0.0549(15) 0.0487(14) 0.0753(17) 0.0073(13) 0.0139(13) -0.0041(13) C15 0.0630(17) 0.0543(16) 0.094(2) 0.0023(16) 0.0317(16) 0.0036(14) C16 0.078(2) 0.0631(18) 0.090(2) -0.0118(17) 0.0389(17) 0.0013(16) C17 0.0703(17) 0.0691(17) 0.0630(16) -0.0078(14) 0.0205(13) -0.0026(15) C18 0.0484(14) 0.0548(15) 0.0525(13) 0.0019(12) 0.0124(11) -0.0057(12) C19 0.0717(19) 0.089(2) 0.0514(15) -0.0129(15) -0.0055(13) 0.0135(16) C22 0.0816(19) 0.095(2) 0.0464(14) 0.0042(15) 0.0088(13) 0.0083(17) C20 0.056(5) 0.109(7) 0.058(5) 0.023(4) -0.006(3) 0.007(5) C21 0.070(4) 0.158(6) 0.101(6) 0.015(5) -0.018(4) -0.009(4) C20B 0.103(11) 0.078(8) 0.054(8) 0.022(6) -0.006(7) -0.030(6) C21B 0.074(9) 0.191(15) 0.065(8) 0.011(8) 0.021(8) 0.015(10) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C7 O1 C11 118.93(18) . . C1 N1 H1 111.6(14) . . C1 N1 C8 123.2(2) . . C8 N1 H1 113.0(14) . . N1 C1 C2 121.2(2) . . N1 C1 C6 121.2(2) . . C6 C1 C2 117.6(2) . . C1 C2 C7 121.02(19) . . C3 C2 C1 119.5(2) . . C3 C2 C7 119.3(2) . . C2 C3 H3 119.3 . . C4 C3 C2 121.4(2) . . C4 C3 H3 119.3 . . C3 C4 H4 120.6 . . C3 C4 C5 118.9(2) . . C5 C4 H4 120.6 . . C4 C5 H5 119.2 . . C6 C5 C4 121.6(2) . . C6 C5 H5 119.2 . . C1 C6 H6 119.5 . . C5 C6 C1 121.0(2) . . C5 C6 H6 119.5 . . O1 C7 C2 112.2(2) . . O2 C7 O1 122.1(2) . . O2 C7 C2 125.6(2) . . N1 C8 H8 107.7 . . N1 C8 C9 110.5(2) . . N1 C8 C11 112.87(18) . 3_666 C9 C8 H8 107.7 . . C9 C8 C11 110.08(19) . 3_666 C11 C8 H8 107.7 3_666 . C8 C9 H9 115.8 . . C10 C9 C8 128.4(2) . . C10 C9 H9 115.8 . . C9 C10 H10A 120.0 . . C9 C10 H10B 120.0 . . H10A C10 H10B 120.0 . . O1 C11 C8 108.22(17) . 3_666 O1 C11 H11A 110.1 . . O1 C11 H11B 110.1 . . C8 C11 H11A 110.1 3_666 . C8 C11 H11B 110.1 3_666 . H11A C11 H11B 108.4 . . C18 O3 C22 117.99(19) . . C12 N2 H2 116.3(15) . . C12 N2 C19 124.4(2) . . C19 N2 H2 111.8(15) . . N2 C12 C13 121.6(2) . . N2 C12 C17 121.0(2) . . C17 C12 C13 117.3(2) . . C12 C13 C18 120.7(2) . . C14 C13 C12 119.5(2) . . C14 C13 C18 119.8(2) . . C13 C14 H14 119.3 . . C15 C14 C13 121.5(2) . . C15 C14 H14 119.3 . . C14 C15 H15 120.6 . . C16 C15 C14 118.8(3) . . C16 C15 H15 120.6 . . C15 C16 H16 119.2 . . C15 C16 C17 121.6(3) . . C17 C16 H16 119.2 . . C12 C17 H17 119.4 . . C16 C17 C12 121.2(2) . . C16 C17 H17 119.4 . . O3 C18 C13 112.6(2) . . O4 C18 O3 122.1(2) . . O4 C18 C13 125.2(2) . . N2 C19 H19 108.5 . . N2 C19 H19A 104.9 . . N2 C19 C22 111.9(2) . 3_655 N2 C19 C20 104.1(4) . . N2 C19 C20B 126.5(5) . . C22 C19 H19 108.5 3_655 . C22 C19 H19A 104.9 3_655 . C22 C19 C20 115.1(4) 3_655 . C20 C19 H19 108.5 . . C20B C19 H19A 104.9 . . C20B C19 C22 101.9(6) . 3_655 O3 C22 C19 109.6(2) . 3_655 O3 C22 H22A 109.7 . . O3 C22 H22B 109.7 . . C19 C22 H22A 109.7 3_655 . C19 C22 H22B 109.7 3_655 . H22A C22 H22B 108.2 . . C19 C20 H20 115.4 . . C21 C20 C19 129.2(9) . . C21 C20 H20 115.4 . . C20 C21 H21A 120.0 . . C20 C21 H21B 120.0 . . H21A C21 H21B 120.0 . . C19 C20B H20B 124.0 . . C21B C20B C19 112.0(11) . . C21B C20B H20B 124.0 . . C20B C21B H21C 120.0 . . C20B C21B H21D 120.0 . . H21C C21B H21D 120.0 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C7 1.343(2) . O1 C11 1.444(2) . O2 C7 1.213(2) . N1 H1 0.820(19) . N1 C1 1.384(3) . N1 C8 1.454(3) . C1 C2 1.414(3) . C1 C6 1.396(3) . C2 C3 1.400(3) . C2 C7 1.464(3) . C3 H3 0.9300 . C3 C4 1.366(3) . C4 H4 0.9300 . C4 C5 1.373(4) . C5 H5 0.9300 . C5 C6 1.371(3) . C6 H6 0.9300 . C8 H8 0.9800 . C8 C9 1.501(4) . C8 C11 1.521(3) 3_666 C9 H9 0.9300 . C9 C10 1.286(3) . C10 H10A 0.9300 . C10 H10B 0.9300 . C11 H11A 0.9700 . C11 H11B 0.9700 . O3 C18 1.348(3) . O3 C22 1.449(3) . O4 C18 1.216(2) . N2 H2 0.81(2) . N2 C12 1.361(3) . N2 C19 1.458(3) . C12 C13 1.414(3) . C12 C17 1.406(3) . C13 C14 1.405(3) . C13 C18 1.470(3) . C14 H14 0.9300 . C14 C15 1.377(3) . C15 H15 0.9300 . C15 C16 1.368(4) . C16 H16 0.9300 . C16 C17 1.375(3) . C17 H17 0.9300 . C19 H19 0.9800 . C19 H19A 0.9800 . C19 C22 1.517(4) 3_655 C19 C20 1.525(6) . C19 C20B 1.509(8) . C22 H22A 0.9700 . C22 H22B 0.9700 . C20 H20 0.9300 . C20 C21 1.241(7) . C21 H21A 0.9300 . C21 H21B 0.9300 . C20B H20B 0.9300 . C20B C21B 1.230(9) . C21B H21C 0.9300 . C21B H21D 0.9300 .