#------------------------------------------------------------------------------ #$Date: 2020-05-20 07:20:51 +0300 (Wed, 20 May 2020) $ #$Revision: 252204 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240561.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_7240561 loop_ _publ_author_name 'Bakthadoss, Manickam' 'Surendar, Manickam' _publ_section_title ; Cascade annulation reaction (CAR): highly diastereoselective synthesis of pyranopyrazole scaffolds ; _journal_issue 32 _journal_name_full 'RSC Advances' _journal_page_first 19003 _journal_paper_doi 10.1039/D0RA03400B _journal_volume 10 _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 mixed _atom_sites_solution_primary direct _audit_creation_date 2020-01-13 _audit_creation_method ; Olex2 1.3-alpha (compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938) ; _audit_update_record ; 2020-01-13 deposited with the CCDC. 2020-05-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.498(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.2883(4) _cell_length_b 9.8313(4) _cell_length_c 18.7276(7) _cell_measurement_reflns_used 3809 _cell_measurement_temperature 298 _cell_measurement_theta_max 29.1062 _cell_measurement_theta_min 3.9153 _cell_volume 2036.65(14) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'ShelXS n/a (Sheldrick, 2008)' _diffrn_ambient_temperature 298 _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.880 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -89.00 -64.00 1.0000 10.5300 omega____ theta____ kappa____ phi______ frames - -17.5741 -37.0000 -30.0000 25 #__ type_ start__ end____ width___ exp.time_ 2 omega -94.00 -45.00 1.0000 10.5300 omega____ theta____ kappa____ phi______ frames - -17.5741 178.0000 -150.0000 49 #__ type_ start__ end____ width___ exp.time_ 3 omega -23.00 2.00 1.0000 10.5300 omega____ theta____ kappa____ phi______ frames - -17.5741 -99.0000 60.0000 25 #__ type_ start__ end____ width___ exp.time_ 4 omega -25.00 17.00 1.0000 10.5300 omega____ theta____ kappa____ phi______ frames - -17.5741 -99.0000 30.0000 42 #__ type_ start__ end____ width___ exp.time_ 5 omega 28.00 55.00 1.0000 10.5300 omega____ theta____ kappa____ phi______ frames - -17.5741 0.0000 30.0000 27 #__ type_ start__ end____ width___ exp.time_ 6 omega -87.00 7.00 1.0000 10.5300 omega____ theta____ kappa____ phi______ frames - -17.5741 -37.0000 -120.0000 94 #__ type_ start__ end____ width___ exp.time_ 7 omega -80.00 -54.00 1.0000 10.5300 omega____ theta____ kappa____ phi______ frames - -17.5741 -57.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega -25.00 1.00 1.0000 10.5300 omega____ theta____ kappa____ phi______ frames - -17.5741 -57.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 9 omega 6.00 42.00 1.0000 10.5300 omega____ theta____ kappa____ phi______ frames - -17.5741 73.0000 -6.0000 36 #__ type_ start__ end____ width___ exp.time_ 10 omega -82.00 -56.00 1.0000 10.5300 omega____ theta____ kappa____ phi______ frames - -17.5741 0.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 11 omega 15.00 49.00 1.0000 10.5300 omega____ theta____ kappa____ phi______ frames - 19.3710 -77.0000 90.0000 34 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0620127000 _diffrn_orient_matrix_UB_12 -0.0176198000 _diffrn_orient_matrix_UB_13 0.0101764000 _diffrn_orient_matrix_UB_21 -0.0064626000 _diffrn_orient_matrix_UB_22 -0.0453764000 _diffrn_orient_matrix_UB_23 -0.0299709000 _diffrn_orient_matrix_UB_31 0.0149881000 _diffrn_orient_matrix_UB_32 0.0532575000 _diffrn_orient_matrix_UB_33 -0.0221666000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_unetI/netI 0.0329 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.880 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 15572 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.880 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 29.171 _diffrn_reflns_theta_min 3.923 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.97088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) 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 1.299 _exptl_crystal_description block _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.42 _refine_diff_density_max 0.175 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 277 _refine_ls_number_reflns 4848 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0497 _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^)+(0.0560P)^2^+0.3832P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1155 _refine_ls_wR_factor_ref 0.1334 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3259 _reflns_number_total 4848 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03400b2.cif _cod_data_source_block mb-msp-aa-ss _cod_original_cell_volume 2036.66(14) _cod_database_code 7240561 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C25 H22 N2 O3' _chemical_oxdiff_usercomment 'COLOURLESS BLOCK, 298K, 0.7 0.52 0.42' _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 99.41 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C4(H4), C6(H6) 2.b Aromatic/amide H refined with riding coordinates: C11(H11), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30) 2.c Idealised Me refined as rotating group: C23(H23a,H23b,H23c) 2.d Idealised tetrahedral OH refined as rotating group: O3(H3) ; _shelx_res_file ; TITL MB-MSP-AA-SS in P21/n #14 mb-msp-aa-ss.res created by SHELXL-2018/3 at 22:57:37 on 13-Jan-2020 REM reset to P21/n #14 CELL 0.71073 11.288349 9.83126 18.727629 90 101.4982 90 ZERR 4 0.000446 0.000351 0.000739 0 0.0039 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. 5 PLAN 1 TEMP 24.85 CONF BOND $H HTAB MORE -1 fmap 2 acta 50 REM REM REM WGHT 0.056000 0.383200 FVAR 6.46158 O1 4 0.485547 0.642865 0.138540 11.00000 0.04430 0.05546 = 0.04134 0.01406 0.00867 0.00420 O2 4 0.240760 0.780842 0.229737 11.00000 0.07426 0.03605 = 0.04676 -0.00785 0.00999 0.00959 O3 4 0.332069 0.548684 0.286750 11.00000 0.06156 0.04127 = 0.03686 0.00256 0.01428 -0.00005 AFIX 147 H3 2 0.314555 0.468962 0.292307 11.00000 -1.50000 AFIX 0 C4 1 0.342232 0.570068 0.213529 11.00000 0.04480 0.03178 = 0.03464 -0.00091 0.00949 -0.00023 AFIX 13 H4 2 0.329812 0.483468 0.187182 11.00000 -1.20000 AFIX 0 N5 3 0.395145 0.757641 0.030646 11.00000 0.05679 0.05216 = 0.03782 0.01042 0.00688 0.00424 C6 1 0.470391 0.622146 0.213193 11.00000 0.04730 0.03562 = 0.03539 0.00307 0.00603 -0.00156 AFIX 13 H6 2 0.483215 0.708564 0.239692 11.00000 -1.20000 AFIX 0 C7 1 0.242304 0.671850 0.178439 11.00000 0.04772 0.03302 = 0.03827 -0.00400 0.00862 0.00428 C8 1 0.566131 0.522329 0.247053 11.00000 0.03923 0.04024 = 0.04128 0.00688 0.00463 -0.00504 N9 3 0.285718 0.819041 0.001366 11.00000 0.06465 0.05777 = 0.04324 0.01057 0.00255 0.01160 C10 1 0.120992 0.596712 0.162669 11.00000 0.04471 0.04425 = 0.04415 -0.00057 0.00919 0.00596 C11 1 0.599457 0.416349 0.206365 11.00000 0.05184 0.04995 = 0.04781 0.00421 0.01002 0.00467 AFIX 43 H11 2 0.563976 0.408064 0.157292 11.00000 -1.20000 AFIX 0 C12 1 0.389828 0.705194 0.097072 11.00000 0.04861 0.03770 = 0.03722 0.00528 0.00523 0.00152 C13 1 0.278253 0.727628 0.111720 11.00000 0.04857 0.03696 = 0.04037 0.00228 0.00512 0.00432 C14 1 0.216826 0.800788 0.050261 11.00000 0.05829 0.04718 = 0.04269 0.00310 0.00182 0.00898 C15 1 0.494483 0.766994 -0.005268 11.00000 0.06371 0.04999 = 0.03594 -0.00216 0.01265 -0.00594 C16 1 0.619654 0.532391 0.320156 11.00000 0.05570 0.05431 = 0.04518 0.00290 0.00000 -0.00646 AFIX 43 H16 2 0.598843 0.603685 0.347892 11.00000 -1.20000 AFIX 0 C17 1 0.703707 0.437238 0.352103 11.00000 0.05595 0.07664 = 0.05751 0.01737 -0.01024 -0.00588 AFIX 43 H17 2 0.737746 0.443698 0.401473 11.00000 -1.20000 AFIX 0 C18 1 0.685326 0.322871 0.238526 11.00000 0.05726 0.05913 = 0.07869 0.01242 0.02434 0.01454 AFIX 43 H18 2 0.708173 0.252644 0.210861 11.00000 -1.20000 AFIX 0 C19 1 0.495130 0.866499 -0.057494 11.00000 0.09464 0.05912 = 0.04948 0.00727 0.02321 -0.00053 AFIX 43 H19 2 0.428908 0.923867 -0.070843 11.00000 -1.20000 AFIX 0 C20 1 0.592233 0.680602 0.012479 11.00000 0.07744 0.07378 = 0.04754 0.00659 0.02119 0.00978 AFIX 43 H20 2 0.591670 0.610685 0.045859 11.00000 -1.20000 AFIX 0 C21 1 0.036764 0.609601 0.205618 11.00000 0.07361 0.06179 = 0.08035 -0.01425 0.03951 -0.00573 AFIX 43 H21 2 0.049686 0.670959 0.244187 11.00000 -1.20000 AFIX 0 C22 1 0.737242 0.333572 0.311649 11.00000 0.04534 0.07547 = 0.08458 0.02831 0.00316 0.01053 AFIX 43 H22 2 0.794761 0.270521 0.333264 11.00000 -1.20000 AFIX 0 C23 1 0.093228 0.861225 0.038470 11.00000 0.07107 0.08116 = 0.05888 0.00755 -0.00077 0.03159 AFIX 137 H23A 2 0.092570 0.935088 0.071918 11.00000 -1.50000 H23B 2 0.036395 0.793075 0.046503 11.00000 -1.50000 H23C 2 0.071184 0.894403 -0.010599 11.00000 -1.50000 AFIX 0 C24 1 0.594533 0.880372 -0.089770 11.00000 0.11780 0.07359 = 0.05647 0.00269 0.03791 -0.02098 AFIX 43 H24 2 0.594619 0.947386 -0.124808 11.00000 -1.20000 AFIX 0 C25 1 -0.090227 0.442358 0.136146 11.00000 0.05379 0.08019 = 0.09722 -0.00040 0.01584 -0.01444 AFIX 43 H25 2 -0.160760 0.390883 0.127312 11.00000 -1.20000 AFIX 0 C26 1 0.096837 0.505778 0.106647 11.00000 0.06616 0.11454 = 0.07696 -0.04983 0.03295 -0.03282 AFIX 43 H26 2 0.152460 0.494896 0.076534 11.00000 -1.20000 AFIX 0 C27 1 0.692062 0.797410 -0.070976 11.00000 0.09438 0.10848 = 0.06064 -0.01156 0.03750 -0.01655 AFIX 43 H27 2 0.758732 0.807657 -0.092736 11.00000 -1.20000 AFIX 0 C28 1 -0.007924 0.429436 0.093413 11.00000 0.08566 0.12808 = 0.09072 -0.05222 0.02461 -0.04649 AFIX 43 H28 2 -0.021821 0.368525 0.054646 11.00000 -1.20000 AFIX 0 C29 1 0.690982 0.698922 -0.019805 11.00000 0.08365 0.11627 = 0.05692 -0.00184 0.03171 0.01441 AFIX 43 H29 2 0.758128 0.642923 -0.006363 11.00000 -1.20000 AFIX 0 C30 1 -0.068246 0.531374 0.191932 11.00000 0.06905 0.07958 = 0.12221 -0.00888 0.05329 -0.00919 AFIX 43 H30 2 -0.124277 0.540784 0.221892 11.00000 -1.20000 AFIX 0 H2 2 0.248608 0.742506 0.272793 11.00000 0.09381 HKLF 4 REM MB-MSP-AA-SS in P21/n #14 REM wR2 = 0.1334, GooF = S = 1.035, Restrained GooF = 1.035 for all data REM R1 = 0.0497 for 3259 Fo > 4sig(Fo) and 0.0809 for all 4848 data REM 277 parameters refined using 0 restraints END WGHT 0.0560 0.3832 REM Instructions for potential hydrogen bonds EQIV $1 -x+1/2, y-1/2, -z+1/2 HTAB O3 O2_$1 HTAB C20 O1 HTAB O2 O3 REM Highest difference peak 0.175, deepest hole -0.172, 1-sigma level 0.041 Q1 1 0.1259 0.5708 0.0578 11.00000 0.05 0.18 ; _shelx_res_checksum 92039 _olex2_submission_special_instructions 'No special instructions were received' 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_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.48555(9) 0.64287(12) 0.13854(6) 0.0470(3) Uani 1 1 d . . . . . O2 O 0.24076(11) 0.78084(11) 0.22974(7) 0.0526(3) Uani 1 1 d . . . . . O3 O 0.33207(11) 0.54868(11) 0.28675(5) 0.0459(3) Uani 1 1 d . . . . . H3 H 0.314555 0.468962 0.292307 0.069 Uiso 1 1 calc R U . . . C4 C 0.34223(13) 0.57007(14) 0.21353(7) 0.0369(3) Uani 1 1 d . . . . . H4 H 0.329812 0.483468 0.187182 0.044 Uiso 1 1 calc R U . . . N5 N 0.39514(13) 0.75764(14) 0.03065(7) 0.0493(3) Uani 1 1 d . . . . . C6 C 0.47039(13) 0.62215(15) 0.21319(8) 0.0397(3) Uani 1 1 d . . . . . H6 H 0.483215 0.708564 0.239692 0.048 Uiso 1 1 calc R U . . . C7 C 0.24230(13) 0.67185(15) 0.17844(8) 0.0397(3) Uani 1 1 d . . . . . C8 C 0.56613(13) 0.52233(15) 0.24705(8) 0.0407(3) Uani 1 1 d . . . . . N9 N 0.28572(14) 0.81904(16) 0.00137(8) 0.0564(4) Uani 1 1 d . . . . . C10 C 0.12099(14) 0.59671(16) 0.16267(9) 0.0443(4) Uani 1 1 d . . . . . C11 C 0.59946(15) 0.41635(17) 0.20636(9) 0.0499(4) Uani 1 1 d . . . . . H11 H 0.563976 0.408064 0.157292 0.060 Uiso 1 1 calc R U . . . C12 C 0.38983(14) 0.70519(15) 0.09707(8) 0.0416(3) Uani 1 1 d . . . . . C13 C 0.27825(14) 0.72763(15) 0.11172(8) 0.0425(4) Uani 1 1 d . . . . . C14 C 0.21683(16) 0.80079(17) 0.05026(9) 0.0505(4) Uani 1 1 d . . . . . C15 C 0.49448(16) 0.76699(17) -0.00527(8) 0.0495(4) Uani 1 1 d . . . . . C16 C 0.61965(16) 0.53239(19) 0.32016(9) 0.0531(4) Uani 1 1 d . . . . . H16 H 0.598843 0.603685 0.347892 0.064 Uiso 1 1 calc R U . . . C17 C 0.70371(17) 0.4372(2) 0.35210(11) 0.0663(5) Uani 1 1 d . . . . . H17 H 0.737746 0.443698 0.401473 0.080 Uiso 1 1 calc R U . . . C18 C 0.68533(16) 0.3229(2) 0.23853(12) 0.0635(5) Uani 1 1 d . . . . . H18 H 0.708173 0.252644 0.210861 0.076 Uiso 1 1 calc R U . . . C19 C 0.4951(2) 0.8665(2) -0.05749(10) 0.0665(5) Uani 1 1 d . . . . . H19 H 0.428908 0.923867 -0.070843 0.080 Uiso 1 1 calc R U . . . C20 C 0.59223(19) 0.6806(2) 0.01248(10) 0.0650(5) Uani 1 1 d . . . . . H20 H 0.591670 0.610685 0.045859 0.078 Uiso 1 1 calc R U . . . C21 C 0.03676(19) 0.6096(2) 0.20562(12) 0.0686(6) Uani 1 1 d . . . . . H21 H 0.049686 0.670959 0.244187 0.082 Uiso 1 1 calc R U . . . C22 C 0.73724(16) 0.3336(2) 0.31165(13) 0.0698(6) Uani 1 1 d . . . . . H22 H 0.794761 0.270521 0.333264 0.084 Uiso 1 1 calc R U . . . C23 C 0.09323(18) 0.8612(2) 0.03847(11) 0.0723(6) Uani 1 1 d . . . . . H23A H 0.092570 0.935088 0.071918 0.108 Uiso 1 1 calc R U . . . H23B H 0.036395 0.793075 0.046503 0.108 Uiso 1 1 calc R U . . . H23C H 0.071184 0.894403 -0.010599 0.108 Uiso 1 1 calc R U . . . C24 C 0.5945(3) 0.8804(2) -0.08977(12) 0.0798(7) Uani 1 1 d . . . . . H24 H 0.594619 0.947386 -0.124808 0.096 Uiso 1 1 calc R U . . . C25 C -0.09023(19) 0.4424(2) 0.13615(14) 0.0770(6) Uani 1 1 d . . . . . H25 H -0.160760 0.390883 0.127312 0.092 Uiso 1 1 calc R U . . . C26 C 0.09684(19) 0.5058(3) 0.10665(12) 0.0833(7) Uani 1 1 d . . . . . H26 H 0.152460 0.494896 0.076534 0.100 Uiso 1 1 calc R U . . . C27 C 0.6921(2) 0.7974(3) -0.07098(12) 0.0848(7) Uani 1 1 d . . . . . H27 H 0.758732 0.807657 -0.092736 0.102 Uiso 1 1 calc R U . . . C28 C -0.0079(2) 0.4294(3) 0.09341(14) 0.1005(9) Uani 1 1 d . . . . . H28 H -0.021821 0.368525 0.054646 0.121 Uiso 1 1 calc R U . . . C29 C 0.6910(2) 0.6989(3) -0.01981(11) 0.0832(7) Uani 1 1 d . . . . . H29 H 0.758128 0.642923 -0.006363 0.100 Uiso 1 1 calc R U . . . C30 C -0.0682(2) 0.5314(3) 0.19193(15) 0.0855(7) Uani 1 1 d . . . . . H30 H -0.124277 0.540784 0.221892 0.103 Uiso 1 1 calc R U . . . H2 H 0.249(2) 0.743(3) 0.2728(13) 0.094(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 0.0443(6) 0.0555(7) 0.0413(6) 0.0141(5) 0.0087(5) 0.0042(5) O2 0.0743(8) 0.0360(6) 0.0468(7) -0.0079(5) 0.0100(6) 0.0096(6) O3 0.0616(7) 0.0413(6) 0.0369(6) 0.0026(5) 0.0143(5) 0.0000(5) C4 0.0448(8) 0.0318(7) 0.0346(7) -0.0009(6) 0.0095(6) -0.0002(6) N5 0.0568(8) 0.0522(8) 0.0378(7) 0.0104(6) 0.0069(6) 0.0042(7) C6 0.0473(8) 0.0356(8) 0.0354(7) 0.0031(6) 0.0060(6) -0.0016(7) C7 0.0477(8) 0.0330(7) 0.0383(8) -0.0040(6) 0.0086(6) 0.0043(6) C8 0.0392(8) 0.0402(8) 0.0413(8) 0.0069(7) 0.0046(6) -0.0050(7) N9 0.0647(9) 0.0578(9) 0.0432(8) 0.0106(7) 0.0025(7) 0.0116(7) C10 0.0447(8) 0.0443(8) 0.0441(8) -0.0006(7) 0.0092(7) 0.0060(7) C11 0.0518(9) 0.0499(9) 0.0478(9) 0.0042(8) 0.0100(7) 0.0047(8) C12 0.0486(9) 0.0377(8) 0.0372(8) 0.0053(7) 0.0052(6) 0.0015(7) C13 0.0486(9) 0.0370(8) 0.0404(8) 0.0023(7) 0.0051(7) 0.0043(7) C14 0.0583(10) 0.0472(9) 0.0427(9) 0.0031(7) 0.0018(8) 0.0090(8) C15 0.0637(10) 0.0500(9) 0.0359(8) -0.0022(7) 0.0126(7) -0.0059(8) C16 0.0557(10) 0.0543(10) 0.0452(9) 0.0029(8) 0.0000(7) -0.0065(8) C17 0.0560(11) 0.0766(14) 0.0575(11) 0.0174(11) -0.0102(9) -0.0059(10) C18 0.0573(11) 0.0591(11) 0.0787(13) 0.0124(10) 0.0243(10) 0.0145(9) C19 0.0946(15) 0.0591(11) 0.0495(10) 0.0073(9) 0.0232(10) -0.0005(11) C20 0.0774(13) 0.0738(13) 0.0475(10) 0.0066(10) 0.0212(9) 0.0098(11) C21 0.0736(13) 0.0618(12) 0.0803(14) -0.0142(10) 0.0395(11) -0.0057(10) C22 0.0453(10) 0.0755(14) 0.0846(15) 0.0283(12) 0.0032(10) 0.0105(10) C23 0.0711(12) 0.0812(14) 0.0589(11) 0.0075(11) -0.0008(10) 0.0316(11) C24 0.1178(19) 0.0736(14) 0.0565(12) 0.0027(11) 0.0379(13) -0.0210(14) C25 0.0538(12) 0.0802(15) 0.0972(16) -0.0004(14) 0.0158(11) -0.0144(11) C26 0.0662(12) 0.1145(18) 0.0770(14) -0.0498(14) 0.0329(11) -0.0328(13) C27 0.0944(17) 0.1085(19) 0.0606(13) -0.0116(13) 0.0375(12) -0.0165(16) C28 0.0857(16) 0.128(2) 0.0907(17) -0.0522(17) 0.0246(14) -0.0465(16) C29 0.0836(15) 0.1163(19) 0.0569(12) -0.0018(13) 0.0317(11) 0.0144(14) C30 0.0691(14) 0.0796(15) 0.122(2) -0.0089(15) 0.0533(14) -0.0092(12) 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 C12 O1 C6 112.53(11) . . ? C7 O2 H2 106.3(16) . . ? C4 O3 H3 109.5 . . ? O3 C4 H4 109.1 . . ? O3 C4 C6 108.18(11) . . ? O3 C4 C7 108.28(11) . . ? C6 C4 H4 109.1 . . ? C6 C4 C7 112.89(12) . . ? C7 C4 H4 109.1 . . ? N9 N5 C15 120.65(13) . . ? C12 N5 N9 109.20(13) . . ? C12 N5 C15 129.86(14) . . ? O1 C6 C4 109.97(11) . . ? O1 C6 H6 109.3 . . ? O1 C6 C8 106.50(12) . . ? C4 C6 H6 109.3 . . ? C8 C6 C4 112.29(12) . . ? C8 C6 H6 109.3 . . ? O2 C7 C4 107.54(11) . . ? O2 C7 C10 110.97(12) . . ? O2 C7 C13 109.04(12) . . ? C10 C7 C4 108.48(12) . . ? C13 C7 C4 107.17(12) . . ? C13 C7 C10 113.42(12) . . ? C11 C8 C6 120.65(14) . . ? C16 C8 C6 120.36(15) . . ? C16 C8 C11 118.96(15) . . ? C14 N9 N5 105.48(13) . . ? C21 C10 C7 122.77(15) . . ? C26 C10 C7 119.89(15) . . ? C26 C10 C21 117.20(17) . . ? C8 C11 H11 119.9 . . ? C18 C11 C8 120.22(16) . . ? C18 C11 H11 119.9 . . ? O1 C12 N5 121.61(14) . . ? O1 C12 C13 128.83(14) . . ? N5 C12 C13 109.57(13) . . ? C12 C13 C7 121.78(13) . . ? C12 C13 C14 103.99(14) . . ? C14 C13 C7 134.12(15) . . ? N9 C14 C13 111.74(15) . . ? N9 C14 C23 120.24(15) . . ? C13 C14 C23 127.93(16) . . ? C19 C15 N5 119.73(17) . . ? C20 C15 N5 120.99(15) . . ? C20 C15 C19 119.25(17) . . ? C8 C16 H16 119.8 . . ? C17 C16 C8 120.42(18) . . ? C17 C16 H16 119.8 . . ? C16 C17 H17 119.8 . . ? C22 C17 C16 120.46(18) . . ? C22 C17 H17 119.8 . . ? C11 C18 H18 119.9 . . ? C22 C18 C11 120.18(19) . . ? C22 C18 H18 119.9 . . ? C15 C19 H19 120.1 . . ? C24 C19 C15 119.8(2) . . ? C24 C19 H19 120.1 . . ? C15 C20 H20 120.3 . . ? C15 C20 C29 119.38(19) . . ? C29 C20 H20 120.3 . . ? C10 C21 H21 119.8 . . ? C10 C21 C30 120.41(19) . . ? C30 C21 H21 119.8 . . ? C17 C22 C18 119.74(18) . . ? C17 C22 H22 120.1 . . ? C18 C22 H22 120.1 . . ? C14 C23 H23A 109.5 . . ? C14 C23 H23B 109.5 . . ? C14 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 C24 H24 119.6 . . ? C27 C24 C19 120.9(2) . . ? C27 C24 H24 119.6 . . ? C28 C25 H25 120.7 . . ? C30 C25 H25 120.7 . . ? C30 C25 C28 118.7(2) . . ? C10 C26 H26 119.1 . . ? C10 C26 C28 121.81(19) . . ? C28 C26 H26 119.1 . . ? C24 C27 H27 120.4 . . ? C24 C27 C29 119.2(2) . . ? C29 C27 H27 120.4 . . ? C25 C28 C26 120.6(2) . . ? C25 C28 H28 119.7 . . ? C26 C28 H28 119.7 . . ? C20 C29 H29 119.3 . . ? C27 C29 C20 121.4(2) . . ? C27 C29 H29 119.3 . . ? C21 C30 H30 119.3 . . ? C25 C30 C21 121.3(2) . . ? C25 C30 H30 119.3 . . ? 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 O1 C6 1.4563(17) . ? O1 C12 1.3459(18) . ? O2 C7 1.4415(17) . ? O2 H2 0.88(2) . ? O3 H3 0.8200 . ? O3 C4 1.4144(16) . ? C4 H4 0.9800 . ? C4 C6 1.536(2) . ? C4 C7 1.552(2) . ? N5 N9 1.3859(19) . ? N5 C12 1.3590(19) . ? N5 C15 1.421(2) . ? C6 H6 0.9800 . ? C6 C8 1.503(2) . ? C7 C10 1.532(2) . ? C7 C13 1.493(2) . ? C8 C11 1.386(2) . ? C8 C16 1.385(2) . ? N9 C14 1.326(2) . ? C10 C21 1.368(2) . ? C10 C26 1.364(2) . ? C11 H11 0.9300 . ? C11 C18 1.384(2) . ? C12 C13 1.359(2) . ? C13 C14 1.416(2) . ? C14 C23 1.492(2) . ? C15 C19 1.384(2) . ? C15 C20 1.380(3) . ? C16 H16 0.9300 . ? C16 C17 1.381(3) . ? C17 H17 0.9300 . ? C17 C22 1.368(3) . ? C18 H18 0.9300 . ? C18 C22 1.382(3) . ? C19 H19 0.9300 . ? C19 C24 1.383(3) . ? C20 H20 0.9300 . ? C20 C29 1.382(3) . ? C21 H21 0.9300 . ? C21 C30 1.393(3) . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24 0.9300 . ? C24 C27 1.359(3) . ? C25 H25 0.9300 . ? C25 C28 1.348(3) . ? C25 C30 1.347(3) . ? C26 H26 0.9300 . ? C26 C28 1.381(3) . ? C27 H27 0.9300 . ? C27 C29 1.364(3) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C6 C8 C11 -36.38(18) . . . . ? O1 C6 C8 C16 145.72(15) . . . . ? O1 C12 C13 C7 -5.3(3) . . . . ? O1 C12 C13 C14 178.07(15) . . . . ? O2 C7 C10 C21 -15.6(2) . . . . ? O2 C7 C10 C26 168.89(18) . . . . ? O2 C7 C13 C12 105.75(16) . . . . ? O2 C7 C13 C14 -78.8(2) . . . . ? O3 C4 C6 O1 178.83(11) . . . . ? O3 C4 C6 C8 60.42(15) . . . . ? O3 C4 C7 O2 44.64(15) . . . . ? O3 C4 C7 C10 -75.44(14) . . . . ? O3 C4 C7 C13 161.75(12) . . . . ? C4 C6 C8 C11 84.04(17) . . . . ? C4 C6 C8 C16 -93.85(17) . . . . ? C4 C7 C10 C21 102.36(18) . . . . ? C4 C7 C10 C26 -73.2(2) . . . . ? C4 C7 C13 C12 -10.37(19) . . . . ? C4 C7 C13 C14 165.09(17) . . . . ? N5 N9 C14 C13 -0.24(19) . . . . ? N5 N9 C14 C23 176.58(16) . . . . ? N5 C12 C13 C7 175.14(14) . . . . ? N5 C12 C13 C14 -1.50(18) . . . . ? N5 C15 C19 C24 176.61(17) . . . . ? N5 C15 C20 C29 -175.38(18) . . . . ? C6 O1 C12 N5 166.89(14) . . . . ? C6 O1 C12 C13 -12.6(2) . . . . ? C6 C4 C7 O2 -75.11(15) . . . . ? C6 C4 C7 C10 164.81(12) . . . . ? C6 C4 C7 C13 42.00(15) . . . . ? C6 C8 C11 C18 -178.25(15) . . . . ? C6 C8 C16 C17 177.11(15) . . . . ? C7 C4 C6 O1 -61.37(15) . . . . ? C7 C4 C6 C8 -179.77(12) . . . . ? C7 C10 C21 C30 -175.26(18) . . . . ? C7 C10 C26 C28 175.8(2) . . . . ? C7 C13 C14 N9 -174.94(16) . . . . ? C7 C13 C14 C23 8.5(3) . . . . ? C8 C11 C18 C22 0.8(3) . . . . ? C8 C16 C17 C22 1.5(3) . . . . ? N9 N5 C12 O1 -178.16(13) . . . . ? N9 N5 C12 C13 1.45(18) . . . . ? N9 N5 C15 C19 18.0(2) . . . . ? N9 N5 C15 C20 -163.73(16) . . . . ? C10 C7 C13 C12 -130.07(15) . . . . ? C10 C7 C13 C14 45.4(2) . . . . ? C10 C21 C30 C25 -0.6(4) . . . . ? C10 C26 C28 C25 -0.2(4) . . . . ? C11 C8 C16 C17 -0.8(2) . . . . ? C11 C18 C22 C17 -0.2(3) . . . . ? C12 O1 C6 C4 43.92(16) . . . . ? C12 O1 C6 C8 165.83(12) . . . . ? C12 N5 N9 C14 -0.72(18) . . . . ? C12 N5 C15 C19 -155.06(17) . . . . ? C12 N5 C15 C20 23.2(3) . . . . ? C12 C13 C14 N9 1.08(19) . . . . ? C12 C13 C14 C23 -175.43(18) . . . . ? C13 C7 C10 C21 -138.69(17) . . . . ? C13 C7 C10 C26 45.8(2) . . . . ? C15 N5 N9 C14 -175.12(15) . . . . ? C15 N5 C12 O1 -4.4(3) . . . . ? C15 N5 C12 C13 175.17(16) . . . . ? C15 C19 C24 C27 0.0(3) . . . . ? C15 C20 C29 C27 -2.5(3) . . . . ? C16 C8 C11 C18 -0.3(2) . . . . ? C16 C17 C22 C18 -0.9(3) . . . . ? C19 C15 C20 C29 2.9(3) . . . . ? C19 C24 C27 C29 0.3(4) . . . . ? C20 C15 C19 C24 -1.6(3) . . . . ? C21 C10 C26 C28 0.0(4) . . . . ? C24 C27 C29 C20 0.9(4) . . . . ? C26 C10 C21 C30 0.4(3) . . . . ? C28 C25 C30 C21 0.3(4) . . . . ? C30 C25 C28 C26 0.1(4) . . . . ?