#------------------------------------------------------------------------------ #$Date: 2020-02-11 04:11:12 +0200 (Tue, 11 Feb 2020) $ #$Revision: 248018 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557288.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_1557288 loop_ _publ_author_name 'Zhang, Xiang' 'Li, Xiang' 'Li, Jun-Long' 'Wang, Qiwei' 'Zou, Wen-Lin' 'Liu, Yan-Qing' 'Jia, Zhi-Qiang' 'Peng, Fu' 'Han, Bo' _publ_section_title ; Regiodivergent Construction of Medium-Sized Heterocycles from Vinylethylene Carbonates and Allylidenemalononitriles ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC06377C _journal_year 2020 _chemical_formula_moiety 'C25 H22 N2 O3' _chemical_formula_sum 'C25 H22 N2 O3' _chemical_formula_weight 398.44 _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 geom _atom_sites_solution_primary direct _audit_creation_date 2018-07-27 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-07-29 deposited with the CCDC. 2020-02-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.745(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.6576(5) _cell_length_b 13.2796(9) _cell_length_c 17.3578(10) _cell_measurement_reflns_used 3528 _cell_measurement_temperature 295.4(4) _cell_measurement_theta_max 72.3720 _cell_measurement_theta_min 4.1830 _cell_volume 2194.0(2) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (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 (Sheldrick, 2015)' _diffrn_ambient_environment air _diffrn_ambient_temperature 295.4(4) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9595 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.977 _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 -104.00 -20.00 1.00 2.16 -- -36.42 -57.00 -60.00 84 2 \w -104.00 -20.00 1.00 2.16 -- -36.42 -57.00 0.00 84 3 \w -33.00 55.00 1.00 2.16 -- 36.42 -38.00 30.00 88 4 \w -31.00 53.00 1.00 2.16 -- 36.42 -57.00 -90.00 84 5 \w -31.00 53.00 1.00 2.16 -- 36.42 -57.00 150.00 84 6 \w 1.00 75.00 1.00 2.16 -- 36.42 -99.00-120.00 74 7 \w 39.00 109.00 1.00 8.65 -- 108.71 -94.00-150.00 70 8 \w 70.00 178.00 1.00 8.65 -- 108.71 15.00-180.00 108 9 \w 91.00 177.00 1.00 8.65 -- 108.71 45.00-120.00 86 10 \w 82.00 176.00 1.00 8.65 -- 108.71 77.00 0.00 94 11 \w 39.00 109.00 1.00 8.65 -- 108.71 -94.00 120.00 70 12 \w 39.00 109.00 1.00 8.65 -- 108.71 -94.00-120.00 70 13 \w 42.00 127.00 1.00 8.65 -- 108.71 -61.00-120.00 85 14 \w 39.00 115.00 1.00 8.65 -- 108.71-111.00 90.00 76 15 \w -104.00 -20.00 1.00 2.16 -- -36.42 -57.00-180.00 84 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'New Gemini, Dual, Cu at zero, EosS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0691408000 _diffrn_orient_matrix_UB_12 -0.0548264000 _diffrn_orient_matrix_UB_13 -0.0619522000 _diffrn_orient_matrix_UB_21 -0.0490574000 _diffrn_orient_matrix_UB_22 0.0843871000 _diffrn_orient_matrix_UB_23 -0.0591563000 _diffrn_orient_matrix_UB_31 0.1377925000 _diffrn_orient_matrix_UB_32 0.0577319000 _diffrn_orient_matrix_UB_33 0.0278571000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_unetI/netI 0.0183 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 12330 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.063 _diffrn_reflns_theta_min 4.215 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.642 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68574 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.206 _exptl_crystal_description block _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.181 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 4284 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0752 _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^)+(0.1044P)^2^+0.2485P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1748 _refine_ls_wR_factor_ref 0.1940 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3173 _reflns_number_total 4284 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06377c2.cif _cod_data_source_block lq-zx-0727 _cod_database_code 1557288 _shelx_shelxl_version_number 2014/7 _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 99.93 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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.a Secondary CH2 refined with riding coordinates: C5(H5A,H5B), C15(H15A,H15B), C14(H14A,H14B), C2(H2A,H2B) 2.b Aromatic/amide H refined with riding coordinates: C22(H22), C6(H6), C18(H18), C21(H21), C20(H20), C19(H19), C9(H9), C13(H13), C10(H10), C12(H12), C11(H11) 2.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C) ; _shelx_res_file ; lq-zx-0727.res created by SHELXL-2014/7 TITL lq-zx-0727_a.res in P2(1)/n REM Old TITL lq-zx-0727 in P21/n #14 REM SHELXT solution in P2(1)/n REM R1 0.220, Rweak 0.266, Alpha 0.049, Orientation as input REM Formula found by SHELXT: C24 N4 O2 CELL 1.54184 9.657639 13.279562 17.357806 90 99.7448 90 ZERR 4 0.000502 0.000909 0.000998 0 0.0054 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 100 88 8 12 L.S. 10 PLAN 20 BOND $H LIST 6 fmap 2 acta REM REM REM WGHT 0.104400 0.248500 FVAR 0.53683 O3 4 0.938142 0.590060 0.421848 11.00000 0.05531 0.10985 = 0.10932 -0.00119 0.01586 0.01564 O1 4 0.752809 0.861437 0.507239 11.00000 0.10112 0.11581 = 0.11063 -0.03754 0.01150 -0.00793 C17 1 0.494553 0.706768 0.365504 11.00000 0.05272 0.06627 = 0.06842 0.01000 0.01069 0.00659 C16 1 0.632843 0.758253 0.374389 11.00000 0.05739 0.06795 = 0.07109 0.00048 0.01727 0.00257 C22 1 0.404633 0.724367 0.417743 11.00000 0.05796 0.08238 = 0.07853 0.00064 0.01460 0.00547 AFIX 43 H22 2 0.431307 0.767638 0.459763 11.00000 -1.20000 AFIX 0 C23 1 0.642394 0.838640 0.328492 11.00000 0.07193 0.07559 = 0.09329 0.01045 0.02538 -0.00042 C6 1 0.666129 0.538649 0.452012 11.00000 0.07002 0.08197 = 0.07236 0.01814 0.02359 0.01529 AFIX 43 H6 2 0.574364 0.520788 0.455692 11.00000 -1.20000 AFIX 0 C5 1 0.716214 0.637814 0.487379 11.00000 0.06350 0.09511 = 0.06622 0.00478 0.01332 0.01991 AFIX 23 H5A 2 0.796736 0.625689 0.527934 11.00000 -1.20000 H5B 2 0.642521 0.666290 0.512302 11.00000 -1.20000 AFIX 0 C4 1 0.758218 0.716911 0.429826 11.00000 0.05268 0.08448 = 0.07639 -0.00139 0.01336 0.00311 O2 4 0.963427 0.803029 0.496259 11.00000 0.07108 0.18122 = 0.16506 -0.03583 -0.01246 -0.01913 C18 1 0.453562 0.641919 0.303454 11.00000 0.06433 0.09642 = 0.07318 -0.00136 0.01061 0.00051 AFIX 43 H18 2 0.512764 0.630245 0.267353 11.00000 -1.20000 AFIX 0 C7 1 0.737457 0.473210 0.415995 11.00000 0.07291 0.08250 = 0.07128 0.01209 0.01684 0.01873 C21 1 0.274284 0.677617 0.407760 11.00000 0.05838 0.10500 = 0.09243 0.01079 0.02225 0.00370 AFIX 43 H21 2 0.212969 0.690884 0.442447 11.00000 -1.20000 AFIX 0 C8 1 0.675345 0.376011 0.384819 11.00000 0.09590 0.08101 = 0.07773 0.01620 0.02623 0.01750 C15 1 0.856941 0.665891 0.379502 11.00000 0.06000 0.10572 = 0.09388 0.00460 0.02684 0.01008 AFIX 23 H15A 2 0.801121 0.636892 0.333090 11.00000 -1.20000 H15B 2 0.918563 0.716172 0.362915 11.00000 -1.20000 AFIX 0 C25 1 0.766561 0.898220 0.328778 11.00000 0.09512 0.08097 = 0.11139 0.00656 0.03514 -0.01340 N2 3 0.861904 0.947835 0.327743 11.00000 0.12577 0.10883 = 0.15663 -0.00870 0.05519 -0.04217 C14 1 0.885697 0.491633 0.403532 11.00000 0.06913 0.10969 = 0.10532 -0.01394 0.01793 0.02258 AFIX 23 H14A 2 0.946825 0.443887 0.435075 11.00000 -1.20000 H14B 2 0.890806 0.477938 0.349193 11.00000 -1.20000 AFIX 0 C3 1 0.838908 0.798571 0.480940 11.00000 0.07287 0.11044 = 0.09775 -0.01068 0.00463 -0.00795 C20 1 0.235828 0.612464 0.347443 11.00000 0.05800 0.10244 = 0.10411 0.00657 0.00684 -0.01017 AFIX 43 H20 2 0.149291 0.580097 0.341679 11.00000 -1.20000 AFIX 0 C19 1 0.324558 0.594537 0.295206 11.00000 0.07040 0.10347 = 0.09279 -0.01264 0.00037 -0.00841 AFIX 43 H19 2 0.297777 0.550174 0.253914 11.00000 -1.20000 AFIX 0 C9 1 0.532705 0.365684 0.356532 11.00000 0.10204 0.08525 = 0.11357 0.00999 0.02827 0.00152 AFIX 43 H9 2 0.474019 0.421192 0.356627 11.00000 -1.20000 AFIX 0 C24 1 0.520547 0.874056 0.276733 11.00000 0.09051 0.09769 = 0.12591 0.04848 0.03796 0.01540 C13 1 0.758558 0.291288 0.382631 11.00000 0.12589 0.08638 = 0.10645 0.00794 0.03165 0.02874 AFIX 43 H13 2 0.854849 0.295652 0.400151 11.00000 -1.20000 AFIX 0 N1 3 0.424843 0.903008 0.235998 11.00000 0.11118 0.17171 = 0.17970 0.10449 0.03240 0.03730 C10 1 0.476167 0.274724 0.328263 11.00000 0.13026 0.10068 = 0.13875 -0.00121 0.03096 -0.01687 AFIX 43 H10 2 0.380339 0.269955 0.309438 11.00000 -1.20000 AFIX 0 C12 1 0.700632 0.200616 0.354852 11.00000 0.18486 0.08317 = 0.13179 0.00952 0.05719 0.03448 AFIX 43 H12 2 0.758005 0.144433 0.354483 11.00000 -1.20000 AFIX 0 C11 1 0.558534 0.192594 0.327656 11.00000 0.17653 0.09328 = 0.14309 -0.00558 0.05646 -0.01216 AFIX 43 H11 2 0.519756 0.131340 0.309092 11.00000 -1.20000 AFIX 0 C2 1 0.817506 0.941445 0.559411 11.00000 0.17049 0.16007 = 0.16070 -0.08091 -0.00409 -0.02114 AFIX 23 H2A 2 0.852339 0.913205 0.610558 11.00000 -1.20000 H2B 2 0.896847 0.969252 0.539000 11.00000 -1.20000 AFIX 0 C1 1 0.724691 1.016033 0.566572 11.00000 0.24579 0.12743 = 0.20808 -0.07013 -0.02535 0.03003 AFIX 137 H1A 2 0.697436 1.048715 0.516992 11.00000 -1.50000 H1B 2 0.767744 1.064228 0.604419 11.00000 -1.50000 H1C 2 0.643164 0.987975 0.583377 11.00000 -1.50000 AFIX 0 HKLF 4 REM lq-zx-0727_a.res in P2(1)/n REM R1 = 0.0608 for 3173 Fo > 4sig(Fo) and 0.0752 for all 4284 data REM 272 parameters refined using 0 restraints END WGHT 0.1043 0.2487 REM Highest difference peak 0.181, deepest hole -0.221, 1-sigma level 0.040 Q1 1 0.7835 1.0217 0.5098 11.00000 0.05 0.18 Q2 1 0.5002 0.9420 0.2487 11.00000 0.05 0.16 Q3 1 0.6736 0.8411 0.5196 11.00000 0.05 0.16 Q4 1 0.6945 0.8995 0.4622 11.00000 0.05 0.14 Q5 1 0.8576 0.9395 0.5685 11.00000 0.05 0.12 Q6 1 0.6265 1.0235 0.5144 11.00000 0.05 0.12 Q7 1 0.6672 0.6819 0.5239 11.00000 0.05 0.12 Q8 1 0.9159 0.7735 0.5457 11.00000 0.05 0.12 Q9 1 0.4289 0.8022 0.4345 11.00000 0.05 0.11 Q10 1 0.7984 0.5923 0.5195 11.00000 0.05 0.11 Q11 1 0.7347 0.9260 0.5951 11.00000 0.05 0.11 Q12 1 0.8678 0.5198 0.3042 11.00000 0.05 0.11 Q13 1 0.8291 0.6807 0.3178 11.00000 0.05 0.10 Q14 1 0.7750 0.8019 0.5151 11.00000 0.05 0.10 Q15 1 0.9152 0.9168 0.5900 11.00000 0.05 0.10 Q16 1 0.7805 0.6293 0.3152 11.00000 0.05 0.10 Q17 1 0.6980 0.7433 0.4036 11.00000 0.05 0.10 Q18 1 0.4445 0.7443 0.4850 11.00000 0.05 0.10 Q19 1 0.9135 0.4378 0.3643 11.00000 0.05 0.09 Q20 1 0.7528 0.4842 0.5553 11.00000 0.05 0.09 ; _shelx_res_checksum 38242 _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 - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.523 _oxdiff_exptl_absorpt_empirical_full_min 0.790 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 O3 O 0.93814(14) 0.59006(14) 0.42185(10) 0.0913(5) Uani 1 1 d . O1 O 0.7528(2) 0.86144(16) 0.50724(12) 0.1099(6) Uani 1 1 d . C17 C 0.49455(17) 0.70677(14) 0.36550(10) 0.0624(4) Uani 1 1 d . C16 C 0.63284(18) 0.75825(14) 0.37439(11) 0.0647(4) Uani 1 1 d . C22 C 0.40463(19) 0.72437(16) 0.41774(12) 0.0726(5) Uani 1 1 d . H22 H 0.4313 0.7676 0.4598 0.087 Uiso 1 1 calc R C23 C 0.6424(2) 0.83864(17) 0.32849(13) 0.0789(6) Uani 1 1 d . C6 C 0.6661(2) 0.53865(16) 0.45201(11) 0.0734(5) Uani 1 1 d . H6 H 0.5744 0.5208 0.4557 0.088 Uiso 1 1 calc R C5 C 0.7162(2) 0.63781(17) 0.48738(11) 0.0747(5) Uani 1 1 d . H5A H 0.7967 0.6257 0.5279 0.090 Uiso 1 1 calc R H5B H 0.6425 0.6663 0.5123 0.090 Uiso 1 1 calc R C4 C 0.75822(19) 0.71691(16) 0.42983(12) 0.0709(5) Uani 1 1 d . O2 O 0.9634(2) 0.8030(2) 0.49626(15) 0.1429(9) Uani 1 1 d . C18 C 0.4536(2) 0.64192(18) 0.30345(12) 0.0781(6) Uani 1 1 d . H18 H 0.5128 0.6302 0.2674 0.094 Uiso 1 1 calc R C7 C 0.7375(2) 0.47321(17) 0.41599(12) 0.0750(5) Uani 1 1 d . C21 C 0.2743(2) 0.67762(19) 0.40776(14) 0.0842(6) Uani 1 1 d . H21 H 0.2130 0.6909 0.4424 0.101 Uiso 1 1 calc R C8 C 0.6753(3) 0.37601(18) 0.38482(13) 0.0835(6) Uani 1 1 d . C15 C 0.8569(2) 0.6659(2) 0.37950(14) 0.0849(6) Uani 1 1 d . H15A H 0.8011 0.6369 0.3331 0.102 Uiso 1 1 calc R H15B H 0.9186 0.7162 0.3629 0.102 Uiso 1 1 calc R C25 C 0.7666(3) 0.89822(19) 0.32878(16) 0.0938(7) Uani 1 1 d . N2 N 0.8619(3) 0.9478(2) 0.32774(18) 0.1268(9) Uani 1 1 d . C14 C 0.8857(2) 0.4916(2) 0.40353(16) 0.0943(7) Uani 1 1 d . H14A H 0.9468 0.4439 0.4351 0.113 Uiso 1 1 calc R H14B H 0.8908 0.4779 0.3492 0.113 Uiso 1 1 calc R C3 C 0.8389(3) 0.7986(2) 0.48094(16) 0.0948(7) Uani 1 1 d . C20 C 0.2358(2) 0.6125(2) 0.34744(15) 0.0890(7) Uani 1 1 d . H20 H 0.1493 0.5801 0.3417 0.107 Uiso 1 1 calc R C19 C 0.3246(2) 0.5945(2) 0.29521(15) 0.0904(7) Uani 1 1 d . H19 H 0.2978 0.5502 0.2539 0.109 Uiso 1 1 calc R C9 C 0.5327(3) 0.3657(2) 0.35653(17) 0.0991(7) Uani 1 1 d . H9 H 0.4740 0.4212 0.3566 0.119 Uiso 1 1 calc R C24 C 0.5205(3) 0.8741(2) 0.27673(18) 0.1024(8) Uani 1 1 d . C13 C 0.7586(4) 0.2913(2) 0.38263(17) 0.1049(8) Uani 1 1 d . H13 H 0.8548 0.2957 0.4002 0.126 Uiso 1 1 calc R N1 N 0.4248(3) 0.9030(3) 0.2360(2) 0.1533(13) Uani 1 1 d . C10 C 0.4762(4) 0.2747(3) 0.3283(2) 0.1223(10) Uani 1 1 d . H10 H 0.3803 0.2700 0.3094 0.147 Uiso 1 1 calc R C12 C 0.7006(5) 0.2006(2) 0.3549(2) 0.1297(12) Uani 1 1 d . H12 H 0.7580 0.1444 0.3545 0.156 Uiso 1 1 calc R C11 C 0.5585(5) 0.1926(3) 0.3277(2) 0.1342(12) Uani 1 1 d . H11 H 0.5198 0.1313 0.3091 0.161 Uiso 1 1 calc R C2 C 0.8175(5) 0.9414(4) 0.5594(3) 0.1675(18) Uani 1 1 d . H2A H 0.8523 0.9132 0.6106 0.201 Uiso 1 1 calc R H2B H 0.8968 0.9693 0.5390 0.201 Uiso 1 1 calc R C1 C 0.7247(6) 1.0160(3) 0.5666(4) 0.201(3) Uani 1 1 d . H1A H 0.6974 1.0487 0.5170 0.302 Uiso 1 1 calc GR H1B H 0.7677 1.0642 0.6044 0.302 Uiso 1 1 calc GR H1C H 0.6432 0.9880 0.5834 0.302 Uiso 1 1 calc GR 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 O3 0.0553(7) 0.1099(12) 0.1093(11) -0.0012(9) 0.0159(7) 0.0156(8) O1 0.1011(12) 0.1158(14) 0.1106(13) -0.0375(11) 0.0115(10) -0.0079(11) C17 0.0527(9) 0.0663(10) 0.0684(9) 0.0100(8) 0.0107(7) 0.0066(7) C16 0.0574(9) 0.0679(11) 0.0711(10) 0.0005(8) 0.0173(7) 0.0026(8) C22 0.0580(10) 0.0824(13) 0.0785(11) 0.0006(9) 0.0146(8) 0.0055(9) C23 0.0719(12) 0.0756(12) 0.0933(13) 0.0104(11) 0.0254(10) -0.0004(10) C6 0.0700(11) 0.0820(13) 0.0724(11) 0.0181(9) 0.0236(8) 0.0153(10) C5 0.0635(10) 0.0951(14) 0.0662(10) 0.0048(10) 0.0133(8) 0.0199(10) C4 0.0527(9) 0.0845(12) 0.0764(11) -0.0014(9) 0.0134(8) 0.0031(8) O2 0.0711(11) 0.181(2) 0.165(2) -0.0358(18) -0.0125(12) -0.0191(12) C18 0.0643(11) 0.0964(15) 0.0732(11) -0.0014(10) 0.0106(9) 0.0005(10) C7 0.0729(11) 0.0825(13) 0.0713(10) 0.0121(9) 0.0168(9) 0.0187(10) C21 0.0584(10) 0.1050(16) 0.0924(14) 0.0108(13) 0.0223(9) 0.0037(11) C8 0.0959(15) 0.0810(14) 0.0777(12) 0.0162(10) 0.0262(11) 0.0175(12) C15 0.0600(11) 0.1057(16) 0.0939(14) 0.0046(12) 0.0268(10) 0.0101(11) C25 0.0951(16) 0.0810(14) 0.1114(17) 0.0066(13) 0.0351(13) -0.0134(13) N2 0.1258(19) 0.1088(17) 0.157(2) -0.0087(16) 0.0552(17) -0.0422(16) C14 0.0691(12) 0.1097(19) 0.1053(16) -0.0139(14) 0.0179(11) 0.0226(12) C3 0.0729(14) 0.1104(19) 0.0978(16) -0.0107(14) 0.0046(11) -0.0080(13) C20 0.0580(11) 0.1024(17) 0.1041(16) 0.0066(13) 0.0068(10) -0.0102(11) C19 0.0704(12) 0.1035(17) 0.0928(14) -0.0126(13) 0.0004(11) -0.0084(12) C9 0.1020(18) 0.0853(15) 0.1136(18) 0.0100(14) 0.0283(14) 0.0015(13) C24 0.0905(16) 0.0977(18) 0.126(2) 0.0485(16) 0.0380(15) 0.0154(14) C13 0.126(2) 0.0864(17) 0.1065(18) 0.0079(14) 0.0317(15) 0.0287(15) N1 0.1112(18) 0.172(3) 0.180(3) 0.104(2) 0.0324(18) 0.0373(19) C10 0.130(2) 0.101(2) 0.139(3) -0.0012(19) 0.031(2) -0.0169(19) C12 0.185(4) 0.0832(19) 0.132(3) 0.0095(17) 0.057(3) 0.034(2) C11 0.177(4) 0.093(2) 0.143(3) -0.0056(19) 0.056(3) -0.012(2) C2 0.170(4) 0.160(4) 0.161(3) -0.081(3) -0.004(3) -0.021(3) C1 0.246(6) 0.127(3) 0.208(5) -0.070(3) -0.025(4) 0.030(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C15 O3 C14 113.37(18) C3 O1 C2 116.5(3) C22 C17 C16 120.64(18) C22 C17 C18 119.27(18) C18 C17 C16 120.08(16) C17 C16 C4 120.45(16) C23 C16 C17 117.05(17) C23 C16 C4 122.41(18) C17 C22 H22 120.0 C17 C22 C21 120.1(2) C21 C22 H22 120.0 C16 C23 C25 125.2(2) C16 C23 C24 120.03(19) C24 C23 C25 114.7(2) C5 C6 H6 116.2 C7 C6 H6 116.2 C7 C6 C5 127.6(2) C6 C5 H5A 108.4 C6 C5 H5B 108.4 C6 C5 C4 115.66(16) H5A C5 H5B 107.4 C4 C5 H5A 108.4 C4 C5 H5B 108.4 C16 C4 C5 112.73(15) C16 C4 C15 107.53(16) C16 C4 C3 112.67(18) C5 C4 C15 108.62(17) C3 C4 C5 105.66(18) C3 C4 C15 109.55(18) C17 C18 H18 120.1 C19 C18 C17 119.9(2) C19 C18 H18 120.1 C6 C7 C8 122.0(2) C6 C7 C14 122.9(2) C8 C7 C14 115.11(19) C22 C21 H21 119.9 C20 C21 C22 120.3(2) C20 C21 H21 119.9 C9 C8 C7 122.0(2) C13 C8 C7 121.0(2) C13 C8 C9 117.1(3) O3 C15 C4 111.09(18) O3 C15 H15A 109.4 O3 C15 H15B 109.4 C4 C15 H15A 109.4 C4 C15 H15B 109.4 H15A C15 H15B 108.0 N2 C25 C23 177.7(3) O3 C14 C7 115.48(18) O3 C14 H14A 108.4 O3 C14 H14B 108.4 C7 C14 H14A 108.4 C7 C14 H14B 108.4 H14A C14 H14B 107.5 O1 C3 C4 111.23(19) O2 C3 O1 124.5(3) O2 C3 C4 124.2(3) C21 C20 H20 120.0 C21 C20 C19 120.0(2) C19 C20 H20 120.0 C18 C19 H19 119.8 C20 C19 C18 120.4(2) C20 C19 H19 119.8 C8 C9 H9 119.3 C10 C9 C8 121.4(3) C10 C9 H9 119.3 N1 C24 C23 179.3(4) C8 C13 H13 119.5 C12 C13 C8 121.0(3) C12 C13 H13 119.5 C9 C10 H10 119.6 C11 C10 C9 120.7(3) C11 C10 H10 119.6 C13 C12 H12 119.7 C11 C12 C13 120.6(3) C11 C12 H12 119.7 C10 C11 C12 119.2(3) C10 C11 H11 120.4 C12 C11 H11 120.4 O1 C2 H2A 109.3 O1 C2 H2B 109.3 H2A C2 H2B 108.0 C1 C2 O1 111.5(4) C1 C2 H2A 109.3 C1 C2 H2B 109.3 C2 C1 H1A 109.5 C2 C1 H1B 109.5 C2 C1 H1C 109.5 H1A C1 H1B 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O3 C15 1.405(3) O3 C14 1.418(3) O1 C3 1.313(3) O1 C2 1.466(4) C17 C16 1.485(2) C17 C22 1.378(3) C17 C18 1.383(3) C16 C23 1.344(3) C16 C4 1.516(3) C22 H22 0.9300 C22 C21 1.388(3) C23 C25 1.436(3) C23 C24 1.434(3) C6 H6 0.9300 C6 C5 1.498(3) C6 C7 1.329(3) C5 H5A 0.9700 C5 H5B 0.9700 C5 C4 1.550(3) C4 C15 1.553(3) C4 C3 1.529(3) O2 C3 1.188(3) C18 H18 0.9300 C18 C19 1.381(3) C7 C8 1.486(3) C7 C14 1.504(3) C21 H21 0.9300 C21 C20 1.361(3) C8 C9 1.389(4) C8 C13 1.387(3) C15 H15A 0.9700 C15 H15B 0.9700 C25 N2 1.135(3) C14 H14A 0.9700 C14 H14B 0.9700 C20 H20 0.9300 C20 C19 1.370(3) C19 H19 0.9300 C9 H9 0.9300 C9 C10 1.381(4) C24 N1 1.132(3) C13 H13 0.9300 C13 C12 1.380(5) C10 H10 0.9300 C10 C11 1.351(5) C12 H12 0.9300 C12 C11 1.378(5) C11 H11 0.9300 C2 H2A 0.9700 C2 H2B 0.9700 C2 C1 1.356(6) C1 H1A 0.9600 C1 H1B 0.9600 C1 H1C 0.9600