#------------------------------------------------------------------------------ #$Date: 2020-05-30 07:11:14 +0300 (Sat, 30 May 2020) $ #$Revision: 252476 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240591.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_7240591 loop_ _publ_author_name 'Mousavi, S. Hekmat' 'Mohammadizadeh, Mohammad Reza' 'Arimitsu, Satoru' 'Saberi, Dariush' 'Poorsadeghi, Samira' 'Genta, Kojya' _publ_section_title ; Metal-free syntheses of new azocines via addition reactions of enaminones with acenaphthoquinone followed by oxidative cleavages of the corresponding vicinal diols ; _journal_issue 35 _journal_name_full 'RSC Advances' _journal_page_first 20552 _journal_paper_doi 10.1039/D0RA02852E _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C27 H23 N O4' _chemical_formula_sum 'C27 H23 N O4' _chemical_formula_weight 425.46 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-10-16 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2020-01-09 deposited with the CCDC. 2020-05-22 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.347(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.4024(2) _cell_length_b 11.0210(3) _cell_length_c 17.2462(3) _cell_measurement_reflns_used 13381 _cell_measurement_temperature 113 _cell_measurement_theta_max 31.0980 _cell_measurement_theta_min 1.7900 _cell_volume 2167.22(8) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _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_temperature 113 _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.937 _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 -110.00 70.00 0.50 32.00 -- -20.00 45.00 0.00 360 2 \w -110.00 70.00 0.50 32.00 -- -20.00 45.00 90.00 360 3 \w -110.00 70.00 0.50 32.00 -- -20.00 45.00 45.00 360 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'Rigaku Saturn724Plus with AFC10' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0162647000 _diffrn_orient_matrix_UB_12 -0.0444085000 _diffrn_orient_matrix_UB_13 0.0276924000 _diffrn_orient_matrix_UB_21 0.0470844000 _diffrn_orient_matrix_UB_22 0.0184996000 _diffrn_orient_matrix_UB_23 0.0243300000 _diffrn_orient_matrix_UB_31 -0.0372500000 _diffrn_orient_matrix_UB_32 0.0427680000 _diffrn_orient_matrix_UB_33 0.0182344000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_unetI/netI 0.0507 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.937 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 30540 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.937 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.162 _diffrn_reflns_theta_min 1.786 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.78766 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.304 _exptl_crystal_description prism _exptl_crystal_F_000 896 _exptl_crystal_preparation 'It has been crysalized from a acetonitrile solusion' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.322 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 292 _refine_ls_number_reflns 6555 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0546 _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^)+(0.0400P)^2^+0.9820P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1084 _refine_ls_wR_factor_ref 0.1215 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4869 _reflns_number_total 6555 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02852e2.cif _cod_data_source_block 191008irai _cod_database_code 7240591 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C27 H23 N1 O4' _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 93.63 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.09 _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), C11(H11A,H11B) 2.b Aromatic/amide H refined with riding coordinates: C15(H15), C6(H6), C1(H1), C19(H19), C4(H4), C3(H3), C2(H2), C17(H17), C18(H18), C5(H5) 2.c Idealised Me refined as rotating group: C26(H26A,H26B,H26C), C25(H25A,H25B,H25C), C24(H24A,H24B,H24C) ; _shelx_res_file ; TITL 191008irai_a.res in P2(1)/c 191008irai.res created by SHELXL-2018/3 at 10:14:46 on 16-Oct-2019 REM Old TITL 191008irai in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.141, Rweak 0.020, Alpha 0.026 REM 0.626 for 248 systematic absences, Orientation as input REM Formula found by SHELXT: C27 N2 O3 CELL 0.71073 11.4024 11.021 17.2462 90 90.347 90 ZERR 4 0.0002 0.0003 0.0003 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 108 92 4 16 L.S. 20 PLAN 20 BOND list 4 fmap 2 acta REM REM REM WGHT 0.040000 0.982000 FVAR 0.49217 O21 4 0.508717 0.374682 0.345217 11.00000 0.02318 0.02888 = 0.02139 0.00611 -0.00282 0.00495 O23 4 0.228566 0.283016 0.185427 11.00000 0.02244 0.02328 = 0.02837 0.00050 0.00083 -0.00455 O22 4 0.169366 0.507187 0.068916 11.00000 0.02673 0.03436 = 0.01789 -0.00213 -0.00472 0.00312 O20 4 0.046157 0.310394 0.465572 11.00000 0.02998 0.08138 = 0.01913 0.00792 -0.00053 -0.02709 N8 3 0.349982 0.490789 0.316577 11.00000 0.01690 0.02227 = 0.01466 0.00142 -0.00049 0.00189 C7 1 0.458384 0.442434 0.300027 11.00000 0.01659 0.01805 = 0.01672 -0.00114 -0.00284 -0.00153 C13A 1 0.408600 0.355193 0.132134 11.00000 0.01905 0.01546 = 0.01893 0.00208 -0.00030 0.00255 C12 1 0.199630 0.560928 0.127629 11.00000 0.01564 0.02593 = 0.01609 0.00223 0.00124 0.00173 C6A 1 0.521259 0.484288 0.227771 11.00000 0.01479 0.01861 = 0.01855 0.00243 -0.00101 0.00231 C13 1 0.295364 0.366982 0.174009 11.00000 0.01727 0.02156 = 0.01492 0.00082 -0.00276 -0.00047 C3A 1 0.598228 0.443905 0.098121 11.00000 0.02066 0.02137 = 0.01964 0.00405 0.00268 0.00483 C15 1 0.196483 0.401588 0.395544 11.00000 0.01997 0.02996 = 0.01402 -0.00233 -0.00199 -0.00122 AFIX 43 H15 2 0.165411 0.366184 0.350990 11.00000 -1.20000 AFIX 0 C9 1 0.240597 0.677306 0.278231 11.00000 0.02278 0.02034 = 0.02014 -0.00152 -0.00123 0.00137 AFIX 23 H9A 2 0.306765 0.732508 0.276189 11.00000 -1.20000 H9B 2 0.210792 0.678114 0.330789 11.00000 -1.20000 AFIX 0 C10 1 0.144256 0.723018 0.222808 11.00000 0.01948 0.02016 = 0.02106 0.00031 -0.00058 0.00349 C6 1 0.610846 0.565534 0.239884 11.00000 0.01937 0.02420 = 0.02198 -0.00001 -0.00139 -0.00198 AFIX 43 H6 2 0.617339 0.604757 0.287462 11.00000 -1.20000 AFIX 0 C1 1 0.407206 0.293002 0.062865 11.00000 0.02676 0.01687 = 0.02337 -0.00247 -0.00194 0.00193 AFIX 43 H1 2 0.343170 0.244324 0.050450 11.00000 -1.20000 AFIX 0 C16 1 0.141824 0.384468 0.466999 11.00000 0.01850 0.03766 = 0.01825 0.00233 -0.00061 -0.00147 C11 1 0.182754 0.694406 0.139752 11.00000 0.02704 0.02327 = 0.02081 0.00538 -0.00057 0.00365 AFIX 23 H11A 2 0.123890 0.724068 0.103605 11.00000 -1.20000 H11B 2 0.255689 0.736328 0.129065 11.00000 -1.20000 AFIX 0 C19 1 0.344366 0.525228 0.457217 11.00000 0.02675 0.02129 = 0.01972 -0.00140 -0.00342 -0.00321 AFIX 43 H19 2 0.412797 0.570862 0.454239 11.00000 -1.20000 AFIX 0 C4 1 0.689920 0.527309 0.113262 11.00000 0.01934 0.03153 = 0.02740 0.00706 0.00519 0.00009 AFIX 43 H4 2 0.748316 0.539170 0.076619 11.00000 -1.20000 AFIX 0 C3 1 0.592408 0.377612 0.027631 11.00000 0.02778 0.02713 = 0.02053 0.00272 0.00669 0.00625 AFIX 43 H3 2 0.652694 0.386006 -0.008051 11.00000 -1.20000 AFIX 0 C2 1 0.501014 0.301889 0.010594 11.00000 0.03463 0.02252 = 0.01940 -0.00230 0.00257 0.00750 AFIX 43 H2 2 0.500809 0.256784 -0.034981 11.00000 -1.20000 AFIX 0 C17 1 0.186863 0.440192 0.533050 11.00000 0.02606 0.03232 = 0.01499 0.00142 0.00162 0.00703 AFIX 43 H17 2 0.149746 0.431021 0.580560 11.00000 -1.20000 AFIX 0 C18 1 0.287985 0.509742 0.527219 11.00000 0.03415 0.02395 = 0.01578 -0.00383 -0.00448 0.00378 AFIX 43 H18 2 0.318446 0.546730 0.571428 11.00000 -1.20000 AFIX 0 C5 1 0.693143 0.590386 0.181267 11.00000 0.01965 0.02677 = 0.03135 0.00319 -0.00042 -0.00510 AFIX 43 H5 2 0.749774 0.649963 0.189015 11.00000 -1.20000 AFIX 0 C26 1 0.027537 0.659885 0.239070 11.00000 0.01874 0.03477 = 0.03431 -0.00237 0.00376 0.00431 AFIX 137 H26A 2 0.038977 0.573588 0.239358 11.00000 -1.50000 H26B 2 -0.028305 0.680999 0.199433 11.00000 -1.50000 H26C 2 -0.001335 0.685437 0.288629 11.00000 -1.50000 AFIX 0 C25 1 0.129029 0.859947 0.231502 11.00000 0.04151 0.02321 = 0.03723 -0.00255 -0.00522 0.00800 AFIX 137 H25A 2 0.107370 0.878527 0.283879 11.00000 -1.50000 H25B 2 0.068671 0.887545 0.196690 11.00000 -1.50000 H25C 2 0.201470 0.899880 0.219402 11.00000 -1.50000 AFIX 0 C24 1 -0.004214 0.278129 0.538867 11.00000 0.03286 0.09280 = 0.02312 0.01635 0.00044 -0.02389 AFIX 137 H24A 2 -0.065845 0.220068 0.530773 11.00000 -1.50000 H24B 2 -0.035668 0.349361 0.563113 11.00000 -1.50000 H24C 2 0.055203 0.243394 0.571703 11.00000 -1.50000 AFIX 0 C14 1 0.296796 0.471278 0.391391 11.00000 0.01930 0.01994 = 0.01457 0.00087 -0.00028 0.00266 C3A1 1 0.507588 0.427769 0.153745 11.00000 0.01838 0.01528 = 0.01798 0.00328 0.00050 0.00428 C12A 1 0.260217 0.495952 0.191632 11.00000 0.01378 0.01987 = 0.01834 0.00129 0.00142 0.00027 C8A 1 0.281974 0.551825 0.259272 11.00000 0.01524 0.02077 = 0.01597 0.00330 0.00053 0.00009 HKLF 4 REM 191008irai_a.res in P2(1)/c REM wR2 = 0.1215, GooF = S = 1.035, Restrained GooF = 1.035 for all data REM R1 = 0.0546 for 4869 Fo > 4sig(Fo) and 0.0827 for all 6555 data REM 292 parameters refined using 0 restraints END WGHT 0.0398 0.9917 REM Highest difference peak 0.322, deepest hole -0.266, 1-sigma level 0.060 Q1 1 0.1866 0.6946 0.2510 11.00000 0.05 0.32 Q2 1 0.2349 0.4604 0.3902 11.00000 0.05 0.30 Q3 1 0.2360 0.5271 0.1659 11.00000 0.05 0.29 Q4 1 0.5801 0.5019 0.2355 11.00000 0.05 0.28 Q5 1 0.5601 0.4211 0.1305 11.00000 0.05 0.28 Q6 1 0.1809 0.3673 0.4391 11.00000 0.05 0.27 Q7 1 0.2718 0.5283 0.2211 11.00000 0.05 0.26 Q8 1 0.4800 0.2835 0.0470 11.00000 0.05 0.25 Q9 1 0.6421 0.5831 0.2000 11.00000 0.05 0.25 Q10 1 0.5468 0.4492 0.1221 11.00000 0.05 0.24 Q11 1 0.4831 0.4584 0.2566 11.00000 0.05 0.24 Q12 1 -0.0420 0.7211 0.2641 11.00000 0.05 0.24 Q13 1 0.1789 0.3980 0.5005 11.00000 0.05 0.23 Q14 1 0.2431 0.4472 0.5312 11.00000 0.05 0.22 Q15 1 -0.0148 0.1615 0.5149 11.00000 0.05 0.22 Q16 1 0.2732 0.4450 0.1870 11.00000 0.05 0.22 Q17 1 0.7961 0.6467 0.2124 11.00000 0.05 0.22 Q18 1 0.4661 0.3825 0.1496 11.00000 0.05 0.21 Q19 1 0.3015 0.5170 0.4178 11.00000 0.05 0.21 Q20 1 0.1545 0.7169 0.1791 11.00000 0.05 0.21 ; _shelx_res_checksum 27127 _olex2_date_sample_data_collection 2019-10-08 _olex2_date_sample_submission 2019-10-08 _olex2_exptl_crystal_mounting_method 'Mitegen Micromount' _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 1.144 _oxdiff_exptl_absorpt_empirical_full_min 0.843 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O21 O 0.50872(9) 0.37468(10) 0.34522(6) 0.0245(2) Uani 1 1 d . . . . . O23 O 0.22857(9) 0.28302(9) 0.18543(6) 0.0247(2) Uani 1 1 d . . . . . O22 O 0.16937(9) 0.50719(10) 0.06892(6) 0.0263(2) Uani 1 1 d . . . . . O20 O 0.04616(10) 0.31039(14) 0.46557(6) 0.0435(4) Uani 1 1 d . . . . . N8 N 0.34998(10) 0.49079(11) 0.31658(6) 0.0179(2) Uani 1 1 d . . . . . C7 C 0.45838(11) 0.44243(13) 0.30003(8) 0.0171(3) Uani 1 1 d . . . . . C13A C 0.40860(12) 0.35519(12) 0.13213(8) 0.0178(3) Uani 1 1 d . . . . . C12 C 0.19963(11) 0.56093(14) 0.12763(8) 0.0192(3) Uani 1 1 d . . . . . C6A C 0.52126(11) 0.48429(13) 0.22777(8) 0.0173(3) Uani 1 1 d . . . . . C13 C 0.29536(12) 0.36698(13) 0.17401(7) 0.0179(3) Uani 1 1 d . . . . . C3A C 0.59823(12) 0.44391(13) 0.09812(8) 0.0205(3) Uani 1 1 d . . . . . C15 C 0.19648(12) 0.40159(14) 0.39554(8) 0.0213(3) Uani 1 1 d . . . . . H15 H 0.165411 0.366184 0.350990 0.026 Uiso 1 1 calc R . . . . C9 C 0.24060(12) 0.67731(13) 0.27823(8) 0.0211(3) Uani 1 1 d . . . . . H9A H 0.306765 0.732508 0.276189 0.025 Uiso 1 1 calc R . . . . H9B H 0.210792 0.678114 0.330789 0.025 Uiso 1 1 calc R . . . . C10 C 0.14426(12) 0.72302(13) 0.22281(8) 0.0202(3) Uani 1 1 d . . . . . C6 C 0.61085(12) 0.56553(14) 0.23988(8) 0.0219(3) Uani 1 1 d . . . . . H6 H 0.617339 0.604757 0.287462 0.026 Uiso 1 1 calc R . . . . C1 C 0.40721(13) 0.29300(13) 0.06287(8) 0.0223(3) Uani 1 1 d . . . . . H1 H 0.343170 0.244324 0.050450 0.027 Uiso 1 1 calc R . . . . C16 C 0.14182(12) 0.38447(15) 0.46700(8) 0.0248(3) Uani 1 1 d . . . . . C11 C 0.18275(13) 0.69441(14) 0.13975(8) 0.0237(3) Uani 1 1 d . . . . . H11A H 0.123890 0.724068 0.103605 0.028 Uiso 1 1 calc R . . . . H11B H 0.255689 0.736328 0.129065 0.028 Uiso 1 1 calc R . . . . C19 C 0.34437(13) 0.52523(13) 0.45722(8) 0.0226(3) Uani 1 1 d . . . . . H19 H 0.412797 0.570862 0.454239 0.027 Uiso 1 1 calc R . . . . C4 C 0.68992(13) 0.52731(15) 0.11326(9) 0.0261(3) Uani 1 1 d . . . . . H4 H 0.748316 0.539170 0.076619 0.031 Uiso 1 1 calc R . . . . C3 C 0.59241(13) 0.37761(14) 0.02763(8) 0.0251(3) Uani 1 1 d . . . . . H3 H 0.652694 0.386006 -0.008051 0.030 Uiso 1 1 calc R . . . . C2 C 0.50101(14) 0.30189(14) 0.01059(8) 0.0255(3) Uani 1 1 d . . . . . H2 H 0.500809 0.256784 -0.034981 0.031 Uiso 1 1 calc R . . . . C17 C 0.18686(13) 0.44019(14) 0.53305(8) 0.0244(3) Uani 1 1 d . . . . . H17 H 0.149746 0.431021 0.580560 0.029 Uiso 1 1 calc R . . . . C18 C 0.28798(14) 0.50974(14) 0.52722(8) 0.0246(3) Uani 1 1 d . . . . . H18 H 0.318446 0.546730 0.571428 0.030 Uiso 1 1 calc R . . . . C5 C 0.69314(13) 0.59039(14) 0.18127(9) 0.0259(3) Uani 1 1 d . . . . . H5 H 0.749774 0.649963 0.189015 0.031 Uiso 1 1 calc R . . . . C26 C 0.02754(13) 0.65989(16) 0.23907(10) 0.0293(3) Uani 1 1 d . . . . . H26A H 0.038977 0.573588 0.239358 0.044 Uiso 1 1 calc GR . . . . H26B H -0.028305 0.680999 0.199433 0.044 Uiso 1 1 calc GR . . . . H26C H -0.001335 0.685437 0.288629 0.044 Uiso 1 1 calc GR . . . . C25 C 0.12903(16) 0.85995(15) 0.23150(10) 0.0340(4) Uani 1 1 d . . . . . H25A H 0.107370 0.878527 0.283879 0.051 Uiso 1 1 calc GR . . . . H25B H 0.068671 0.887545 0.196690 0.051 Uiso 1 1 calc GR . . . . H25C H 0.201470 0.899880 0.219402 0.051 Uiso 1 1 calc GR . . . . C24 C -0.00421(16) 0.2781(2) 0.53887(10) 0.0496(6) Uani 1 1 d . . . . . H24A H -0.065845 0.220068 0.530773 0.074 Uiso 1 1 calc GR . . . . H24B H -0.035668 0.349361 0.563113 0.074 Uiso 1 1 calc GR . . . . H24C H 0.055203 0.243394 0.571703 0.074 Uiso 1 1 calc GR . . . . C14 C 0.29680(12) 0.47128(13) 0.39139(7) 0.0179(3) Uani 1 1 d . . . . . C3A1 C 0.50759(12) 0.42777(12) 0.15375(8) 0.0172(3) Uani 1 1 d . . . . . C12A C 0.26022(11) 0.49595(13) 0.19163(8) 0.0173(3) Uani 1 1 d . . . . . C8A C 0.28197(11) 0.55182(13) 0.25927(7) 0.0173(3) Uani 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 O21 0.0232(5) 0.0289(6) 0.0214(5) 0.0061(4) -0.0028(4) 0.0050(4) O23 0.0224(5) 0.0233(6) 0.0284(5) 0.0005(4) 0.0008(4) -0.0046(4) O22 0.0267(5) 0.0344(6) 0.0179(5) -0.0021(4) -0.0047(4) 0.0031(5) O20 0.0300(6) 0.0814(10) 0.0191(5) 0.0079(6) -0.0005(5) -0.0271(6) N8 0.0169(5) 0.0223(6) 0.0147(5) 0.0014(5) -0.0005(4) 0.0019(4) C7 0.0166(6) 0.0180(7) 0.0167(6) -0.0011(5) -0.0028(5) -0.0015(5) C13A 0.0190(6) 0.0155(7) 0.0189(6) 0.0021(5) -0.0003(5) 0.0025(5) C12 0.0156(6) 0.0259(8) 0.0161(6) 0.0022(5) 0.0012(5) 0.0017(5) C6A 0.0148(6) 0.0186(7) 0.0186(6) 0.0024(5) -0.0010(5) 0.0023(5) C13 0.0173(6) 0.0216(7) 0.0149(6) 0.0008(5) -0.0028(5) -0.0005(5) C3A 0.0207(6) 0.0214(8) 0.0196(6) 0.0040(5) 0.0027(5) 0.0048(5) C15 0.0200(6) 0.0300(8) 0.0140(6) -0.0023(6) -0.0020(5) -0.0012(6) C9 0.0228(7) 0.0203(8) 0.0201(7) -0.0015(6) -0.0012(5) 0.0014(5) C10 0.0195(6) 0.0202(8) 0.0211(7) 0.0003(5) -0.0006(5) 0.0035(5) C6 0.0194(6) 0.0242(8) 0.0220(7) 0.0000(6) -0.0014(5) -0.0020(5) C1 0.0268(7) 0.0169(7) 0.0234(7) -0.0025(6) -0.0019(5) 0.0019(6) C16 0.0185(6) 0.0377(9) 0.0183(7) 0.0023(6) -0.0006(5) -0.0015(6) C11 0.0270(7) 0.0233(8) 0.0208(7) 0.0054(6) -0.0006(5) 0.0036(6) C19 0.0267(7) 0.0213(8) 0.0197(7) -0.0014(6) -0.0034(5) -0.0032(6) C4 0.0193(7) 0.0315(9) 0.0274(7) 0.0071(6) 0.0052(5) 0.0001(6) C3 0.0278(7) 0.0271(8) 0.0205(7) 0.0027(6) 0.0067(6) 0.0062(6) C2 0.0346(8) 0.0225(8) 0.0194(7) -0.0023(6) 0.0026(6) 0.0075(6) C17 0.0261(7) 0.0323(9) 0.0150(6) 0.0014(6) 0.0016(5) 0.0070(6) C18 0.0341(8) 0.0240(8) 0.0158(6) -0.0038(6) -0.0045(6) 0.0038(6) C5 0.0196(7) 0.0268(9) 0.0314(8) 0.0032(6) -0.0004(6) -0.0051(6) C26 0.0187(7) 0.0348(9) 0.0343(8) -0.0024(7) 0.0038(6) 0.0043(6) C25 0.0415(10) 0.0232(9) 0.0372(9) -0.0026(7) -0.0052(7) 0.0080(7) C24 0.0329(9) 0.0928(17) 0.0231(8) 0.0163(9) 0.0004(7) -0.0239(10) C14 0.0193(6) 0.0199(7) 0.0146(6) 0.0009(5) -0.0003(5) 0.0027(5) C3A1 0.0184(6) 0.0153(7) 0.0180(6) 0.0033(5) 0.0005(5) 0.0043(5) C12A 0.0138(6) 0.0199(7) 0.0183(6) 0.0013(5) 0.0014(5) 0.0003(5) C8A 0.0152(6) 0.0208(7) 0.0160(6) 0.0033(5) 0.0005(5) 0.0001(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 _geom_angle_publ_flag C16 O20 C24 117.18(13) . . ? C7 N8 C14 120.62(11) . . ? C7 N8 C8A 121.69(11) . . ? C8A N8 C14 117.45(11) . . ? O21 C7 N8 121.57(12) . . ? O21 C7 C6A 119.28(12) . . ? N8 C7 C6A 118.87(11) . . ? C1 C13A C13 117.30(12) . . ? C1 C13A C3A1 120.60(13) . . ? C3A1 C13A C13 120.65(12) . . ? O22 C12 C11 123.78(13) . . ? O22 C12 C12A 120.73(13) . . ? C12A C12 C11 115.46(12) . . ? C6 C6A C7 115.41(12) . . ? C6 C6A C3A1 119.83(12) . . ? C3A1 C6A C7 123.60(12) . . ? O23 C13 C13A 123.94(13) . . ? O23 C13 C12A 121.16(12) . . ? C13A C13 C12A 114.35(11) . . ? C4 C3A C3 121.53(13) . . ? C4 C3A C3A1 119.65(13) . . ? C3 C3A C3A1 118.80(13) . . ? C14 C15 C16 119.69(13) . . ? C8A C9 C10 113.07(11) . . ? C11 C10 C9 107.82(11) . . ? C26 C10 C9 110.88(12) . . ? C26 C10 C11 109.40(12) . . ? C25 C10 C9 110.14(12) . . ? C25 C10 C11 109.17(12) . . ? C25 C10 C26 109.40(13) . . ? C6A C6 C5 121.00(14) . . ? C13A C1 C2 121.10(14) . . ? O20 C16 C15 115.23(13) . . ? O20 C16 C17 124.85(13) . . ? C17 C16 C15 119.91(14) . . ? C12 C11 C10 111.71(12) . . ? C18 C19 C14 118.67(14) . . ? C5 C4 C3A 120.39(13) . . ? C2 C3 C3A 122.03(13) . . ? C3 C2 C1 119.14(14) . . ? C18 C17 C16 119.17(13) . . ? C19 C18 C17 121.49(13) . . ? C4 C5 C6 120.19(14) . . ? C15 C14 N8 118.79(12) . . ? C15 C14 C19 121.03(13) . . ? C19 C14 N8 120.14(12) . . ? C6A C3A1 C13A 123.94(12) . . ? C3A C3A1 C13A 117.93(12) . . ? C3A C3A1 C6A 118.13(12) . . ? C12 C12A C13 115.36(11) . . ? C8A C12A C12 120.58(13) . . ? C8A C12A C13 124.06(12) . . ? N8 C8A C9 117.15(11) . . ? C12A C8A N8 118.99(13) . . ? C12A C8A C9 123.85(12) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O21 C7 1.2202(16) . ? O23 C13 1.2153(16) . ? O22 C12 1.2210(17) . ? O20 C16 1.3626(18) . ? O20 C24 1.4363(18) . ? N8 C7 1.3775(17) . ? N8 C14 1.4451(17) . ? N8 C8A 1.4217(17) . ? C7 C6A 1.5134(18) . ? C13A C13 1.4889(18) . ? C13A C1 1.3773(19) . ? C13A C3A1 1.4309(19) . ? C12 C11 1.498(2) . ? C12 C12A 1.4830(18) . ? C6A C6 1.3734(19) . ? C6A C3A1 1.4282(19) . ? C13 C12A 1.508(2) . ? C3A C4 1.415(2) . ? C3A C3 1.420(2) . ? C3A C3A1 1.4255(18) . ? C15 C16 1.3971(19) . ? C15 C14 1.3800(19) . ? C9 C10 1.5367(19) . ? C9 C8A 1.498(2) . ? C10 C11 1.5335(19) . ? C10 C26 1.529(2) . ? C10 C25 1.527(2) . ? C6 C5 1.410(2) . ? C1 C2 1.406(2) . ? C16 C17 1.390(2) . ? C19 C18 1.382(2) . ? C19 C14 1.3889(19) . ? C4 C5 1.364(2) . ? C3 C2 1.366(2) . ? C17 C18 1.389(2) . ? C12A C8A 1.3409(19) . ?