#------------------------------------------------------------------------------ #$Date: 2020-02-11 04:11:12 +0200 (Tue, 11 Feb 2020) $ #$Revision: 248018 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557287.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_1557287 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_absolute_configuration unk _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 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2018-07-05 _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 95.822(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.0919(5) _cell_length_b 9.9836(5) _cell_length_c 11.7719(5) _cell_measurement_reflns_used 2764 _cell_measurement_temperature 296.6(3) _cell_measurement_theta_max 72.8930 _cell_measurement_theta_min 4.8790 _cell_volume 1063.02(9) _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 296.6(3) _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 0.974 _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 -108.00 -7.00 1.00 1.48 -- -36.42 -19.00 150.00 101 2 \w -90.00 -2.00 1.00 1.48 -- -36.42 125.00 150.00 88 3 \w -104.00 -20.00 1.00 1.48 -- -36.42 -57.00 -90.00 84 4 \w 20.00 104.00 1.00 1.48 -- 36.42 57.00 -60.00 84 5 \w 100.00 178.00 1.00 5.92 -- 108.71 111.00-180.00 78 6 \w 39.00 109.00 1.00 5.92 -- 108.71 -94.00-180.00 70 7 \w 91.00 177.00 1.00 5.92 -- 108.71 45.00 90.00 86 8 \w 40.00 126.00 1.00 5.92 -- 108.71 -45.00 120.00 86 9 \w 39.00 178.00 1.00 5.92 -- 108.71 0.00-150.00 139 10 \w 41.00 135.00 1.00 5.92 -- 108.71 -77.00-120.00 94 11 \w -55.00 33.00 1.00 1.48 -- -36.42 38.00 -30.00 88 12 \w 10.00 104.00 1.00 1.48 -- 36.42 77.00 60.00 94 13 \w 23.00 90.00 1.00 1.48 -- 36.42-125.00 60.00 67 14 \w 70.00 102.00 1.00 5.92 -- 108.71 15.00 30.00 32 15 \w 91.00 176.00 1.00 5.92 -- 108.71 61.00 -90.00 85 ; _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 0.1614292000 _diffrn_orient_matrix_UB_12 -0.0464816000 _diffrn_orient_matrix_UB_13 0.0263175000 _diffrn_orient_matrix_UB_21 0.0223890000 _diffrn_orient_matrix_UB_22 0.0106066000 _diffrn_orient_matrix_UB_23 -0.1276711000 _diffrn_orient_matrix_UB_31 0.0495260000 _diffrn_orient_matrix_UB_32 0.1467540000 _diffrn_orient_matrix_UB_33 0.0175693000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_unetI/netI 0.0365 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6415 _diffrn_reflns_point_group_measured_fraction_full 0.822 _diffrn_reflns_point_group_measured_fraction_max 0.788 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.916 _diffrn_reflns_theta_min 3.774 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.662 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.77038 _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 1.245 _exptl_crystal_description plate _exptl_crystal_F_000 420 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.242 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.059 _refine_ls_abs_structure_details ; Flack x determined using 1007 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 3358 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0549 _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^)+(0.1012P)^2^+0.0769P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1433 _refine_ls_wR_factor_ref 0.1472 _reflns_Friedel_coverage 0.525 _reflns_Friedel_fraction_full 0.621 _reflns_Friedel_fraction_max 0.578 _reflns_number_gt 3152 _reflns_number_total 3358 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06377c2.cif _cod_data_source_block lq-zx-180704 _cod_original_cell_volume 1063.02(10) _cod_database_code 1557287 _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 99.90 _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: C9(H9A,H9B), C13(H13A,H13B), C14(H14A,H14B), C24(H24A,H24B) 2.b Aromatic/amide H refined with riding coordinates: C8(H8), C1(H1), C18(H18), C2(H2), C3(H3), C22(H22), C19(H19), C5(H5), C20(H20), C4(H4), C21(H21) 2.c Idealised Me refined as rotating group: C25(H25A,H25B,H25C) ; _shelx_res_file ; lq-zx-180704.res created by SHELXL-2014/7 TITL lq-zx-180704_a.res in P2(1) REM Old TITL lq-zx-180704 in P21 #4 REM SHELXT solution in P2(1) REM R1 0.130, Rweak 0.040, Alpha 0.004, Orientation as input REM Flack x = -0.156 ( 0.408 ) from Parsons' quotients REM Formula found by SHELXT: C25 N3 O2 CELL 1.54184 9.091931 9.983553 11.771921 90 95.8216 90 ZERR 2 0.000505 0.000538 0.000544 0 0.0046 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O UNIT 50 44 4 6 L.S. 10 PLAN 20 BOND $H LIST 6 fmap 2 acta REM REM REM WGHT 0.101200 0.076900 FVAR 11.04379 O1 4 0.689287 0.611874 0.821548 11.00000 0.05598 0.04216 = 0.05356 -0.01124 -0.01022 0.00730 O2 4 0.408179 0.725374 0.628580 11.00000 0.08793 0.05412 = 0.05253 0.01523 0.01260 0.01212 O3 4 0.329190 0.715734 0.799373 11.00000 0.11411 0.07545 = 0.05317 0.00853 0.02598 0.05284 C7 1 0.839793 0.426668 0.763609 11.00000 0.04223 0.04080 = 0.03792 -0.00023 0.00226 0.00130 C6 1 0.973083 0.423556 0.849887 11.00000 0.03685 0.04960 = 0.04019 0.00200 0.00278 -0.00321 C17 1 0.300311 0.443536 0.569113 11.00000 0.04190 0.04296 = 0.04111 0.00776 -0.00438 -0.00140 N2 3 0.522785 0.178089 0.878547 11.00000 0.07053 0.06608 = 0.05358 0.02068 0.00152 0.00791 C23 1 0.393567 0.665453 0.713050 11.00000 0.05012 0.04665 = 0.03759 0.00017 -0.00012 0.01095 C12 1 0.453023 0.527272 0.739995 11.00000 0.04330 0.04191 = 0.03173 0.00247 0.00284 0.00919 N1 3 0.335892 0.102755 0.563656 11.00000 0.06643 0.05276 = 0.06857 -0.00202 -0.01202 -0.01311 C8 1 0.779210 0.313631 0.720424 11.00000 0.04030 0.04171 = 0.04249 -0.00357 0.00190 0.00578 AFIX 43 H8 2 0.820979 0.234546 0.750395 11.00000 -1.20000 AFIX 0 C9 1 0.651778 0.297873 0.629308 11.00000 0.04620 0.04248 = 0.03809 -0.00761 -0.00056 0.00236 AFIX 23 H9A 2 0.667377 0.217467 0.585852 11.00000 -1.20000 H9B 2 0.651644 0.373368 0.577430 11.00000 -1.20000 AFIX 0 C11 1 0.416641 0.426228 0.668471 11.00000 0.03931 0.04414 = 0.03077 0.00502 0.00091 0.00186 C13 1 0.568338 0.528603 0.842514 11.00000 0.05384 0.05003 = 0.03419 -0.00530 -0.00479 0.01098 AFIX 23 H13A 2 0.524161 0.561272 0.908837 11.00000 -1.20000 H13B 2 0.603383 0.438137 0.858612 11.00000 -1.20000 AFIX 0 C15 1 0.402755 0.186477 0.609057 11.00000 0.04819 0.04248 = 0.04889 0.00374 -0.00612 -0.00183 C16 1 0.510137 0.229863 0.792755 11.00000 0.04447 0.04405 = 0.04479 0.00637 -0.00387 0.00494 C1 1 1.065476 0.312657 0.860976 11.00000 0.04735 0.05206 = 0.06243 -0.00080 -0.00394 0.00025 AFIX 43 H1 2 1.045097 0.238777 0.813880 11.00000 -1.20000 AFIX 0 C10 1 0.494422 0.288611 0.675818 11.00000 0.04362 0.04160 = 0.03492 0.00041 -0.00450 -0.00024 C14 1 0.773067 0.561253 0.733726 11.00000 0.05101 0.04130 = 0.04513 0.00237 -0.00561 -0.00325 AFIX 23 H14A 2 0.851324 0.624110 0.721626 11.00000 -1.20000 H14B 2 0.708999 0.554074 0.662910 11.00000 -1.20000 AFIX 0 C18 1 0.331095 0.418811 0.458165 11.00000 0.06417 0.04690 = 0.03966 0.00201 -0.00616 -0.00031 AFIX 43 H18 2 0.424400 0.389192 0.443781 11.00000 -1.20000 AFIX 0 C2 1 1.188682 0.310794 0.942063 11.00000 0.04715 0.06933 = 0.07402 0.01652 -0.00659 0.00432 AFIX 43 H2 2 1.247714 0.234639 0.950239 11.00000 -1.20000 AFIX 0 C3 1 1.223082 0.419718 1.009309 11.00000 0.04646 0.09504 = 0.06492 0.00802 -0.01589 -0.00733 AFIX 43 H3 2 1.304970 0.418069 1.063478 11.00000 -1.20000 AFIX 0 C22 1 0.160283 0.485855 0.589598 11.00000 0.04337 0.09531 = 0.06099 0.01731 0.00151 0.00578 AFIX 43 H22 2 0.138156 0.500596 0.663996 11.00000 -1.20000 AFIX 0 C19 1 0.221648 0.438566 0.368585 11.00000 0.09508 0.06535 = 0.04260 0.00366 -0.01894 -0.01411 AFIX 43 H19 2 0.241681 0.421737 0.293993 11.00000 -1.20000 AFIX 0 C5 1 1.009675 0.533153 0.918698 11.00000 0.04967 0.06081 = 0.06426 -0.01114 -0.01019 0.00209 AFIX 43 H5 2 0.949424 0.608629 0.913088 11.00000 -1.20000 AFIX 0 C20 1 0.083533 0.482970 0.389654 11.00000 0.06903 0.09568 = 0.08014 0.03729 -0.04011 -0.02132 AFIX 43 H20 2 0.010909 0.497129 0.329345 11.00000 -1.20000 AFIX 0 C4 1 1.135829 0.531739 0.996345 11.00000 0.05920 0.08776 = 0.07037 -0.02169 -0.01680 -0.00867 AFIX 43 H4 2 1.161155 0.607585 1.039864 11.00000 -1.20000 AFIX 0 C21 1 0.053596 0.506064 0.498865 11.00000 0.04010 0.12358 = 0.09546 0.03302 -0.01201 0.00385 AFIX 43 H21 2 -0.039865 0.535839 0.512680 11.00000 -1.20000 AFIX 0 C25 1 0.211621 0.896528 0.879108 11.00000 0.18793 0.08481 = 0.10154 -0.01708 0.01233 0.05307 AFIX 137 H25A 2 0.115762 0.855954 0.878030 11.00000 -1.50000 H25B 2 0.201253 0.992203 0.876509 11.00000 -1.50000 H25C 2 0.271098 0.871268 0.947822 11.00000 -1.50000 AFIX 0 C24 1 0.278572 0.853795 0.785971 11.00000 0.18262 0.08935 = 0.09760 0.01291 0.03371 0.07907 AFIX 23 H24A 2 0.362211 0.911326 0.775814 11.00000 -1.20000 H24B 2 0.209085 0.860894 0.718054 11.00000 -1.20000 AFIX 0 HKLF 4 REM lq-zx-180704_a.res in P2(1) REM R1 = 0.0549 for 3152 Fo > 4sig(Fo) and 0.0573 for all 3358 data REM 272 parameters refined using 1 restraints END WGHT 0.1012 0.0769 REM Highest difference peak 0.242, deepest hole -0.291, 1-sigma level 0.059 Q1 1 0.3171 0.9261 0.8458 11.00000 0.05 0.24 Q2 1 0.2603 0.6513 0.7965 11.00000 0.05 0.21 Q3 1 0.1916 0.7980 0.7884 11.00000 0.05 0.20 Q4 1 0.5499 0.4456 0.3611 11.00000 0.05 0.19 Q5 1 0.3113 0.1336 0.6190 11.00000 0.05 0.15 Q6 1 0.1756 0.4558 0.2053 11.00000 0.05 0.15 Q7 1 0.7088 0.7133 0.8153 11.00000 0.05 0.15 Q8 1 0.8349 0.2056 0.7209 11.00000 0.05 0.15 Q9 1 0.5537 0.4250 0.8769 11.00000 0.05 0.15 Q10 1 0.0422 0.7782 0.8690 11.00000 0.05 0.15 Q11 1 -0.0770 0.7995 0.8022 11.00000 0.05 0.15 Q12 1 0.8902 0.2246 0.5668 11.00000 0.05 0.14 Q13 1 0.5173 0.2648 0.8639 11.00000 0.05 0.14 Q14 1 0.0825 0.7597 0.9299 11.00000 0.05 0.14 Q15 1 0.3330 0.9227 0.6804 11.00000 0.05 0.14 Q16 1 0.0715 0.3045 0.6451 11.00000 0.05 0.14 Q17 1 0.6861 0.3962 0.9313 11.00000 0.05 0.14 Q18 1 0.7442 0.1394 0.5172 11.00000 0.05 0.14 Q19 1 0.3554 0.3260 0.2345 11.00000 0.05 0.13 Q20 1 0.4270 0.8355 0.6161 11.00000 0.05 0.13 ; _shelx_res_checksum 68595 _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 1.268 _oxdiff_exptl_absorpt_empirical_full_min 0.726 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 O1 O 0.6893(3) 0.6119(3) 0.8215(2) 0.0516(6) Uani 1 1 d . O2 O 0.4082(3) 0.7254(3) 0.6286(2) 0.0645(7) Uani 1 1 d . O3 O 0.3292(4) 0.7157(4) 0.7994(2) 0.0797(10) Uani 1 1 d . C7 C 0.8398(3) 0.4267(3) 0.7636(2) 0.0404(6) Uani 1 1 d . C6 C 0.9731(3) 0.4236(4) 0.8499(2) 0.0423(6) Uani 1 1 d . C17 C 0.3003(3) 0.4435(4) 0.5691(2) 0.0426(6) Uani 1 1 d . N2 N 0.5228(4) 0.1781(4) 0.8785(3) 0.0637(9) Uani 1 1 d . C23 C 0.3936(4) 0.6655(4) 0.7131(2) 0.0451(7) Uani 1 1 d . C12 C 0.4530(3) 0.5273(3) 0.7400(2) 0.0390(6) Uani 1 1 d . N1 N 0.3359(4) 0.1028(4) 0.5637(3) 0.0639(8) Uani 1 1 d . C8 C 0.7792(3) 0.3136(3) 0.7204(2) 0.0417(6) Uani 1 1 d . H8 H 0.8210 0.2345 0.7504 0.050 Uiso 1 1 calc R C9 C 0.6518(3) 0.2979(3) 0.6293(2) 0.0426(7) Uani 1 1 d . H9A H 0.6674 0.2175 0.5859 0.051 Uiso 1 1 calc R H9B H 0.6516 0.3734 0.5774 0.051 Uiso 1 1 calc R C11 C 0.4166(3) 0.4262(3) 0.6685(2) 0.0383(6) Uani 1 1 d . C13 C 0.5683(4) 0.5286(4) 0.8425(2) 0.0467(7) Uani 1 1 d . H13A H 0.5242 0.5613 0.9088 0.056 Uiso 1 1 calc R H13B H 0.6034 0.4381 0.8586 0.056 Uiso 1 1 calc R C15 C 0.4028(4) 0.1865(4) 0.6091(3) 0.0473(7) Uani 1 1 d . C16 C 0.5101(3) 0.2299(4) 0.7928(3) 0.0450(7) Uani 1 1 d . C1 C 1.0655(4) 0.3127(4) 0.8610(3) 0.0546(8) Uani 1 1 d . H1 H 1.0451 0.2388 0.8139 0.066 Uiso 1 1 calc R C10 C 0.4944(3) 0.2886(3) 0.6758(2) 0.0406(6) Uani 1 1 d . C14 C 0.7731(4) 0.5613(4) 0.7337(3) 0.0465(7) Uani 1 1 d . H14A H 0.8513 0.6241 0.7216 0.056 Uiso 1 1 calc R H14B H 0.7090 0.5541 0.6629 0.056 Uiso 1 1 calc R C18 C 0.3311(4) 0.4188(4) 0.4582(2) 0.0510(8) Uani 1 1 d . H18 H 0.4244 0.3892 0.4438 0.061 Uiso 1 1 calc R C2 C 1.1887(4) 0.3108(5) 0.9421(4) 0.0644(10) Uani 1 1 d . H2 H 1.2477 0.2346 0.9502 0.077 Uiso 1 1 calc R C3 C 1.2231(4) 0.4197(6) 1.0093(3) 0.0703(12) Uani 1 1 d . H3 H 1.3050 0.4181 1.0635 0.084 Uiso 1 1 calc R C22 C 0.1603(4) 0.4859(5) 0.5896(3) 0.0668(12) Uani 1 1 d . H22 H 0.1382 0.5006 0.6640 0.080 Uiso 1 1 calc R C19 C 0.2216(5) 0.4386(5) 0.3686(3) 0.0694(11) Uani 1 1 d . H19 H 0.2417 0.4217 0.2940 0.083 Uiso 1 1 calc R C5 C 1.0097(4) 0.5332(5) 0.9187(3) 0.0593(9) Uani 1 1 d . H5 H 0.9494 0.6086 0.9131 0.071 Uiso 1 1 calc R C20 C 0.0835(5) 0.4830(6) 0.3897(4) 0.0849(16) Uani 1 1 d . H20 H 0.0109 0.4971 0.3293 0.102 Uiso 1 1 calc R C4 C 1.1358(5) 0.5317(6) 0.9963(4) 0.0740(12) Uani 1 1 d . H4 H 1.1612 0.6076 1.0399 0.089 Uiso 1 1 calc R C21 C 0.0536(4) 0.5061(7) 0.4989(5) 0.0877(17) Uani 1 1 d . H21 H -0.0399 0.5358 0.5127 0.105 Uiso 1 1 calc R C25 C 0.2116(11) 0.8965(8) 0.8791(6) 0.125(3) Uani 1 1 d . H25A H 0.1158 0.8560 0.8780 0.187 Uiso 1 1 calc GR H25B H 0.2013 0.9922 0.8765 0.187 Uiso 1 1 calc GR H25C H 0.2711 0.8713 0.9478 0.187 Uiso 1 1 calc GR C24 C 0.2786(10) 0.8538(7) 0.7860(5) 0.122(3) Uani 1 1 d . H24A H 0.3622 0.9113 0.7758 0.146 Uiso 1 1 calc R H24B H 0.2091 0.8609 0.7181 0.146 Uiso 1 1 calc R 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 0.0560(12) 0.0422(13) 0.0536(11) -0.0112(10) -0.0102(9) 0.0073(10) O2 0.0879(18) 0.0541(16) 0.0525(13) 0.0152(12) 0.0126(12) 0.0121(14) O3 0.114(2) 0.075(2) 0.0532(13) 0.0085(14) 0.0260(14) 0.0528(19) C7 0.0422(13) 0.0408(17) 0.0379(11) -0.0002(13) 0.0023(10) 0.0013(12) C6 0.0368(13) 0.0496(19) 0.0402(12) 0.0020(14) 0.0028(10) -0.0032(12) C17 0.0419(14) 0.0430(17) 0.0411(13) 0.0078(13) -0.0044(10) -0.0014(12) N2 0.0705(19) 0.066(2) 0.0536(15) 0.0207(16) 0.0015(13) 0.0079(16) C23 0.0501(16) 0.0467(18) 0.0376(13) 0.0002(13) -0.0001(11) 0.0109(13) C12 0.0433(14) 0.0419(16) 0.0317(12) 0.0025(11) 0.0028(10) 0.0092(12) N1 0.0664(19) 0.0528(19) 0.0686(18) -0.0020(16) -0.0120(15) -0.0131(16) C8 0.0403(13) 0.0417(16) 0.0425(13) -0.0036(12) 0.0019(10) 0.0058(12) C9 0.0462(14) 0.0425(17) 0.0381(12) -0.0076(12) -0.0006(11) 0.0024(13) C11 0.0393(13) 0.0441(16) 0.0308(10) 0.0050(12) 0.0009(9) 0.0019(12) C13 0.0538(16) 0.0500(19) 0.0342(12) -0.0053(13) -0.0048(11) 0.0110(14) C15 0.0482(16) 0.0425(18) 0.0489(15) 0.0037(14) -0.0061(12) -0.0018(13) C16 0.0445(14) 0.0441(17) 0.0448(15) 0.0064(14) -0.0039(11) 0.0049(13) C1 0.0474(16) 0.052(2) 0.0624(18) -0.0008(16) -0.0039(13) 0.0003(15) C10 0.0436(14) 0.0416(17) 0.0349(12) 0.0004(12) -0.0045(10) -0.0002(12) C14 0.0510(16) 0.0413(17) 0.0451(15) 0.0024(13) -0.0056(12) -0.0032(13) C18 0.0642(18) 0.0469(19) 0.0397(13) 0.0020(14) -0.0062(12) -0.0003(15) C2 0.0472(17) 0.069(3) 0.074(2) 0.017(2) -0.0066(15) 0.0043(18) C3 0.0465(17) 0.095(4) 0.0649(19) 0.008(2) -0.0159(15) -0.007(2) C22 0.0434(17) 0.095(4) 0.061(2) 0.017(2) 0.0015(14) 0.0058(19) C19 0.095(3) 0.065(3) 0.0426(15) 0.0037(18) -0.0189(17) -0.014(2) C5 0.0497(17) 0.061(2) 0.0643(19) -0.0111(18) -0.0102(14) 0.0021(16) C20 0.069(3) 0.096(4) 0.080(3) 0.037(3) -0.040(2) -0.021(2) C4 0.059(2) 0.088(3) 0.070(2) -0.022(2) -0.0168(18) -0.009(2) C21 0.0401(18) 0.124(5) 0.095(3) 0.033(3) -0.0120(18) 0.004(2) C25 0.188(8) 0.085(5) 0.102(4) -0.017(4) 0.012(4) 0.053(5) C24 0.183(7) 0.089(5) 0.098(4) 0.013(3) 0.034(4) 0.079(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 C13 O1 C14 113.3(2) C23 O3 C24 115.8(4) C6 C7 C14 117.2(3) C8 C7 C6 121.0(3) C8 C7 C14 121.8(2) C1 C6 C7 121.3(3) C5 C6 C7 120.7(3) C5 C6 C1 118.0(3) C18 C17 C11 121.3(3) C18 C17 C22 119.7(3) C22 C17 C11 119.0(3) O2 C23 O3 123.5(3) O2 C23 C12 125.1(3) O3 C23 C12 111.3(3) C23 C12 C13 111.4(3) C11 C12 C23 120.0(2) C11 C12 C13 128.0(3) C7 C8 H8 115.9 C7 C8 C9 128.2(3) C9 C8 H8 115.9 C8 C9 H9A 108.6 C8 C9 H9B 108.6 C8 C9 C10 114.6(2) H9A C9 H9B 107.6 C10 C9 H9A 108.6 C10 C9 H9B 108.6 C17 C11 C10 115.3(3) C12 C11 C17 120.9(3) C12 C11 C10 123.7(2) O1 C13 C12 110.6(3) O1 C13 H13A 109.5 O1 C13 H13B 109.5 C12 C13 H13A 109.5 C12 C13 H13B 109.5 H13A C13 H13B 108.1 N1 C15 C10 175.5(3) N2 C16 C10 175.9(4) C6 C1 H1 119.6 C6 C1 C2 120.7(4) C2 C1 H1 119.6 C11 C10 C9 110.7(2) C15 C10 C9 109.5(2) C15 C10 C11 110.6(2) C15 C10 C16 102.4(3) C16 C10 C9 109.7(2) C16 C10 C11 113.7(2) O1 C14 C7 112.2(3) O1 C14 H14A 109.2 O1 C14 H14B 109.2 C7 C14 H14A 109.2 C7 C14 H14B 109.2 H14A C14 H14B 107.9 C17 C18 H18 120.2 C17 C18 C19 119.5(4) C19 C18 H18 120.2 C1 C2 H2 119.8 C3 C2 C1 120.5(4) C3 C2 H2 119.8 C2 C3 H3 120.3 C2 C3 C4 119.4(3) C4 C3 H3 120.3 C17 C22 H22 120.2 C21 C22 C17 119.7(4) C21 C22 H22 120.2 C18 C19 H19 119.8 C20 C19 C18 120.3(4) C20 C19 H19 119.8 C6 C5 H5 119.7 C6 C5 C4 120.7(4) C4 C5 H5 119.7 C19 C20 H20 120.1 C21 C20 C19 119.9(3) C21 C20 H20 120.1 C3 C4 C5 120.7(4) C3 C4 H4 119.7 C5 C4 H4 119.7 C22 C21 H21 119.6 C20 C21 C22 120.9(4) C20 C21 H21 119.6 H25A C25 H25B 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 C24 C25 H25A 109.5 C24 C25 H25B 109.5 C24 C25 H25C 109.5 O3 C24 H24A 109.3 O3 C24 H24B 109.3 C25 C24 O3 111.6(6) C25 C24 H24A 109.3 C25 C24 H24B 109.3 H24A C24 H24B 108.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C13 1.420(5) O1 C14 1.437(4) O2 C23 1.179(4) O3 C23 1.322(4) O3 C24 1.457(6) C7 C6 1.500(4) C7 C8 1.334(5) C7 C14 1.501(5) C6 C1 1.388(5) C6 C5 1.382(5) C17 C11 1.505(3) C17 C18 1.385(4) C17 C22 1.386(5) N2 C16 1.130(4) C23 C12 1.504(5) C12 C11 1.334(4) C12 C13 1.516(3) N1 C15 1.135(5) C8 H8 0.9300 C8 C9 1.505(4) C9 H9A 0.9700 C9 H9B 0.9700 C9 C10 1.586(4) C11 C10 1.544(4) C13 H13A 0.9700 C13 H13B 0.9700 C15 C10 1.490(4) C16 C10 1.490(4) C1 H1 0.9300 C1 C2 1.396(5) C14 H14A 0.9700 C14 H14B 0.9700 C18 H18 0.9300 C18 C19 1.389(5) C2 H2 0.9300 C2 C3 1.363(7) C3 H3 0.9300 C3 C4 1.371(7) C22 H22 0.9300 C22 C21 1.383(5) C19 H19 0.9300 C19 C20 1.378(8) C5 H5 0.9300 C5 C4 1.392(5) C20 H20 0.9300 C20 C21 1.361(8) C4 H4 0.9300 C21 H21 0.9300 C25 H25A 0.9600 C25 H25B 0.9600 C25 H25C 0.9600 C25 C24 1.375(9) C24 H24A 0.9700 C24 H24B 0.9700