#------------------------------------------------------------------------------ #$Date: 2020-05-20 07:20:51 +0300 (Wed, 20 May 2020) $ #$Revision: 252204 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240562.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_7240562 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 H18 N2 O3' _chemical_formula_sum 'C25 H18 N2 O3' _chemical_formula_weight 394.41 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date 2020-01-14 _audit_creation_method ; Olex2 1.3-alpha (compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938) ; _audit_update_record ; 2020-01-14 deposited with the CCDC. 2020-05-12 downloaded from the CCDC. ; _cell_angle_alpha 66.900(12) _cell_angle_beta 85.830(10) _cell_angle_gamma 80.391(12) _cell_formula_units_Z 2 _cell_length_a 9.6663(14) _cell_length_b 10.7447(16) _cell_length_c 10.7533(10) _cell_measurement_reflns_used 3906 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.0648 _cell_measurement_theta_min 3.1968 _cell_volume 1012.9(3) _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 ; Superflip n/a (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.865 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 20.00 46.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1835 77.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -46.00 48.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1835 77.0000 120.0000 94 #__ type_ start__ end____ width___ exp.time_ 3 omega -9.00 90.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.8397 77.0000 30.0000 99 #__ type_ start__ end____ width___ exp.time_ 4 omega -10.00 17.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.8397 77.0000 -120.0000 27 #__ type_ start__ end____ width___ exp.time_ 5 omega 49.00 85.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.8397 77.0000 -120.0000 36 #__ type_ start__ end____ width___ exp.time_ 6 omega -10.00 90.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.8397 77.0000 -90.0000 100 #__ type_ start__ end____ width___ exp.time_ 7 omega 35.00 96.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.8397 178.0000 150.0000 61 #__ type_ start__ end____ width___ exp.time_ 8 omega -49.00 41.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.8397 -57.0000 -60.0000 90 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0366611000 _diffrn_orient_matrix_UB_12 0.0568991000 _diffrn_orient_matrix_UB_13 -0.0289094000 _diffrn_orient_matrix_UB_21 -0.0246413000 _diffrn_orient_matrix_UB_22 0.0121762000 _diffrn_orient_matrix_UB_23 -0.0649050000 _diffrn_orient_matrix_UB_31 -0.0598950000 _diffrn_orient_matrix_UB_32 0.0434199000 _diffrn_orient_matrix_UB_33 0.0097125000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_unetI/netI 0.0197 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.865 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 10884 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.865 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 29.127 _diffrn_reflns_theta_min 3.203 _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 0.88672 _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 violet _exptl_crystal_colour_primary violet _exptl_crystal_density_diffrn 1.293 _exptl_crystal_description block _exptl_crystal_F_000 412 _exptl_crystal_size_max 0.82 _exptl_crystal_size_mid 0.72 _exptl_crystal_size_min 0.42 _refine_diff_density_max 0.148 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 4715 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0455 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.1743P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1134 _refine_ls_wR_factor_ref 0.1231 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3745 _reflns_number_total 4715 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03400b2.cif _cod_data_source_block mb-msp-609-s _cod_original_cell_volume 1012.9(2) _cod_database_code 7240562 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C25 H18 N2 O3' _chemical_oxdiff_usercomment 'VIOLET COLOUR BLOCK, 298K, 0.82 0.72 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. ; _shelx_estimated_absorpt_t_max 0.965 _shelx_estimated_absorpt_t_min 0.933 _reflns_odcompleteness_completeness 99.76 _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 2.a Aromatic/amide H refined with riding coordinates: C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D), C1E(H1E), C1F(H1F) 2.b Idealised Me refined as rotating group: C10(H10A,H10B,H10C) ; _shelx_res_file ; TITL CF solution in P-1 mb-msp-609-s.res created by SHELXL-2018/3 at 12:36:39 on 14-Jan-2020 CELL 0.71073 9.666338 10.744741 10.753325 66.9002 85.8299 80.391 ZERR 2 0.001429 0.0016 0.001004 0.0118 0.0101 0.0124 LATT 1 SFAC C H N O UNIT 50 36 4 6 L.S. 4 PLAN 1 SIZE 0.72 0.82 0.42 TEMP 25(2) CONF BOND MORE -1 BOND $H fmap 2 acta 50 OMIT -2 3 3 REM REM REM WGHT 0.055600 0.174300 FVAR 7.96932 O2 4 0.187621 0.164815 1.061828 11.00000 0.06623 0.05482 = 0.06265 -0.01934 0.00813 -0.02318 O3 4 0.498613 0.270081 0.939672 11.00000 0.05546 0.07448 = 0.09259 -0.04398 0.00336 -0.02423 N6 3 0.161802 0.637439 0.707851 11.00000 0.06696 0.03729 = 0.03345 -0.01689 -0.00540 -0.00258 N5 3 0.144423 0.719448 0.784942 11.00000 0.06356 0.04213 = 0.03847 -0.02169 -0.00452 -0.00335 C20 1 0.173536 0.640944 0.909563 11.00000 0.04852 0.04684 = 0.03785 -0.02063 -0.00190 -0.00618 C2 1 0.136897 0.701122 0.566610 11.00000 0.05394 0.04389 = 0.03250 -0.01530 -0.00208 -0.00256 C3 1 0.283932 0.366008 1.168658 11.00000 0.05050 0.04530 = 0.03536 -0.01319 -0.00430 -0.00404 C4 1 0.212156 0.497843 0.925236 11.00000 0.05227 0.04420 = 0.03553 -0.01635 -0.00355 -0.00854 C6 1 0.266959 0.245965 1.008002 11.00000 0.05217 0.04458 = 0.03892 -0.01090 -0.00712 -0.01005 C5 1 0.196700 0.501652 0.786959 11.00000 0.06100 0.04089 = 0.03717 -0.01610 -0.00779 -0.00404 C7 1 0.406254 0.128965 0.851998 11.00000 0.05379 0.03828 = 0.04483 -0.01102 -0.00729 -0.00262 C8 1 0.252006 0.379781 1.030318 11.00000 0.04734 0.04607 = 0.03783 -0.01419 -0.00207 -0.01009 C9 1 0.399674 0.217607 0.929490 11.00000 0.04995 0.04279 = 0.04834 -0.01223 -0.00629 -0.00970 C10 1 0.155732 0.699237 1.016000 11.00000 0.07015 0.06428 = 0.04480 -0.03253 -0.00631 -0.00191 AFIX 137 H10A 2 0.246258 0.700320 1.046504 11.00000 -1.50000 H10B 2 0.103414 0.643932 1.090768 11.00000 -1.50000 H10C 2 0.106077 0.790936 0.979154 11.00000 -1.50000 AFIX 0 C11 1 0.120041 0.841766 0.502846 11.00000 0.07842 0.04454 = 0.04371 -0.01571 -0.00605 -0.01103 AFIX 43 H11 2 0.126219 0.895225 0.551861 11.00000 -1.20000 AFIX 0 C12 1 0.388920 0.430363 1.187790 11.00000 0.06559 0.07278 = 0.04403 -0.02145 -0.00037 -0.02237 AFIX 43 H12 2 0.437518 0.484216 1.113694 11.00000 -1.20000 AFIX 0 C13 1 0.084746 0.826961 0.291312 11.00000 0.08934 0.07302 = 0.03276 -0.01291 -0.00533 -0.00455 AFIX 43 H13 2 0.068591 0.868906 0.198774 11.00000 -1.20000 AFIX 0 C14 1 0.212102 0.286521 1.280906 11.00000 0.05949 0.05780 = 0.04272 -0.01238 -0.00007 -0.01079 AFIX 43 H14 2 0.142220 0.241978 1.269701 11.00000 -1.20000 AFIX 0 C15 1 0.348956 0.335818 1.427534 11.00000 0.08422 0.08478 = 0.03911 -0.02355 -0.01508 0.00480 AFIX 43 H15 2 0.371164 0.325153 1.514203 11.00000 -1.20000 AFIX 0 C16 1 0.291686 0.075729 0.834226 11.00000 0.06398 0.06182 = 0.06552 -0.03035 0.00024 -0.01722 AFIX 43 H16 2 0.205531 0.093984 0.872987 11.00000 -1.20000 AFIX 0 C17 1 0.099801 0.687482 0.355442 11.00000 0.16134 0.07322 = 0.03923 -0.02886 -0.01283 -0.00908 AFIX 43 H17 2 0.092037 0.634969 0.305821 11.00000 -1.20000 AFIX 0 C18 1 0.093742 0.903198 0.364765 11.00000 0.08437 0.05038 = 0.04502 -0.00483 -0.00521 -0.00849 AFIX 43 H18 2 0.082123 0.998086 0.322031 11.00000 -1.20000 AFIX 0 C19 1 0.126357 0.622953 0.492710 11.00000 0.13748 0.04949 = 0.03988 -0.02096 -0.01167 -0.00367 AFIX 43 H19 2 0.136988 0.528043 0.534730 11.00000 -1.20000 AFIX 0 C1A 1 0.244216 0.273521 1.408965 11.00000 0.08086 0.07301 = 0.03728 -0.00933 0.00222 -0.00842 AFIX 43 H1A 2 0.194193 0.221954 1.483251 11.00000 -1.20000 AFIX 0 C1B 1 0.421506 0.414540 1.317122 11.00000 0.07509 0.09223 = 0.05754 -0.03508 -0.01325 -0.01737 AFIX 43 H1B 2 0.492533 0.457138 1.329539 11.00000 -1.20000 AFIX 0 C1C 1 0.305322 -0.004733 0.758720 11.00000 0.09410 0.06252 = 0.06984 -0.03092 -0.01013 -0.02168 AFIX 43 H1C 2 0.228359 -0.040967 0.747687 11.00000 -1.20000 AFIX 0 C1D 1 0.533204 0.102549 0.790661 11.00000 0.05654 0.06565 = 0.06616 -0.02612 -0.00518 -0.00271 AFIX 43 H1D 2 0.610738 0.138564 0.800763 11.00000 -1.20000 AFIX 0 C1E 1 0.431608 -0.031221 0.700201 11.00000 0.10479 0.05647 = 0.06518 -0.03115 -0.01384 0.00775 AFIX 43 H1E 2 0.440404 -0.086150 0.650527 11.00000 -1.20000 AFIX 0 C1F 1 0.544688 0.023172 0.714895 11.00000 0.07560 0.08330 = 0.07389 -0.03966 -0.00264 0.01085 AFIX 43 H1F 2 0.629730 0.006557 0.673602 11.00000 -1.20000 AFIX 0 O1 4 0.212704 0.404472 0.752302 11.00000 0.11216 0.04038 = 0.05061 -0.02231 -0.02419 0.00297 HKLF 4 REM CF solution in P-1 REM wR2 = 0.1231, GooF = S = 1.029, Restrained GooF = 1.029 for all data REM R1 = 0.0455 for 3745 Fo > 4sig(Fo) and 0.0583 for all 4715 data REM 272 parameters refined using 0 restraints END WGHT 0.0556 0.1743 REM Highest difference peak 0.148, deepest hole -0.199, 1-sigma level 0.042 Q1 1 0.3124 0.4373 0.7364 11.00000 0.05 0.15 ; _shelx_res_checksum 67312 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.18762(11) 0.16481(10) 1.06183(11) 0.0610(3) Uani 1 1 d . . . . . O3 O 0.49861(11) 0.27008(12) 0.93967(13) 0.0689(3) Uani 1 1 d . . . . . N6 N 0.16180(12) 0.63744(10) 0.70785(10) 0.0453(3) Uani 1 1 d . . . . . N5 N 0.14442(12) 0.71945(11) 0.78494(11) 0.0465(3) Uani 1 1 d . . . . . C20 C 0.17354(14) 0.64094(13) 0.90956(12) 0.0431(3) Uani 1 1 d . . . . . C2 C 0.13690(14) 0.70112(13) 0.56661(12) 0.0438(3) Uani 1 1 d . . . . . C3 C 0.28393(14) 0.36601(13) 1.16866(12) 0.0447(3) Uani 1 1 d . . . . . C4 C 0.21216(14) 0.49784(13) 0.92524(12) 0.0434(3) Uani 1 1 d . . . . . C6 C 0.26696(14) 0.24596(13) 1.00800(13) 0.0462(3) Uani 1 1 d . . . . . C5 C 0.19670(15) 0.50165(13) 0.78696(13) 0.0461(3) Uani 1 1 d . . . . . C7 C 0.40625(15) 0.12896(13) 0.85200(13) 0.0474(3) Uani 1 1 d . . . . . C8 C 0.25201(14) 0.37978(13) 1.03032(12) 0.0439(3) Uani 1 1 d . . . . . C9 C 0.39967(15) 0.21761(13) 0.92949(14) 0.0481(3) Uani 1 1 d . . . . . C10 C 0.15573(17) 0.69924(16) 1.01600(14) 0.0569(4) Uani 1 1 d . . . . . H10A H 0.246258 0.700320 1.046504 0.085 Uiso 1 1 calc R U . . . H10B H 0.103414 0.643932 1.090768 0.085 Uiso 1 1 calc R U . . . H10C H 0.106077 0.790936 0.979154 0.085 Uiso 1 1 calc R U . . . C11 C 0.12004(17) 0.84177(14) 0.50285(14) 0.0555(4) Uani 1 1 d . . . . . H11 H 0.126219 0.895225 0.551861 0.067 Uiso 1 1 calc R U . . . C12 C 0.38892(17) 0.43036(17) 1.18779(15) 0.0597(4) Uani 1 1 d . . . . . H12 H 0.437518 0.484216 1.113694 0.072 Uiso 1 1 calc R U . . . C13 C 0.0847(2) 0.82696(18) 0.29131(15) 0.0681(4) Uani 1 1 d . . . . . H13 H 0.068591 0.868906 0.198774 0.082 Uiso 1 1 calc R U . . . C14 C 0.21210(16) 0.28652(15) 1.28091(14) 0.0553(4) Uani 1 1 d . . . . . H14 H 0.142220 0.241978 1.269701 0.066 Uiso 1 1 calc R U . . . C15 C 0.3490(2) 0.33582(19) 1.42753(15) 0.0709(5) Uani 1 1 d . . . . . H15 H 0.371164 0.325153 1.514203 0.085 Uiso 1 1 calc R U . . . C16 C 0.29169(18) 0.07573(16) 0.83423(17) 0.0611(4) Uani 1 1 d . . . . . H16 H 0.205531 0.093984 0.872987 0.073 Uiso 1 1 calc R U . . . C17 C 0.0998(3) 0.6875(2) 0.35544(16) 0.0895(7) Uani 1 1 d . . . . . H17 H 0.092037 0.634969 0.305821 0.107 Uiso 1 1 calc R U . . . C18 C 0.09374(19) 0.90320(16) 0.36477(15) 0.0641(4) Uani 1 1 d . . . . . H18 H 0.082123 0.998086 0.322031 0.077 Uiso 1 1 calc R U . . . C19 C 0.1264(2) 0.62295(17) 0.49271(15) 0.0752(5) Uani 1 1 d . . . . . H19 H 0.136988 0.528043 0.534730 0.090 Uiso 1 1 calc R U . . . C1A C 0.2442(2) 0.27352(18) 1.40896(15) 0.0680(4) Uani 1 1 d . . . . . H1A H 0.194193 0.221954 1.483251 0.082 Uiso 1 1 calc R U . . . C1B C 0.4215(2) 0.4145(2) 1.31712(17) 0.0718(5) Uani 1 1 d . . . . . H1B H 0.492533 0.457138 1.329539 0.086 Uiso 1 1 calc R U . . . C1C C 0.3053(2) -0.00473(18) 0.75872(18) 0.0721(5) Uani 1 1 d . . . . . H1C H 0.228359 -0.040967 0.747687 0.087 Uiso 1 1 calc R U . . . C1D C 0.53320(17) 0.10255(17) 0.79066(17) 0.0631(4) Uani 1 1 d . . . . . H1D H 0.610738 0.138564 0.800763 0.076 Uiso 1 1 calc R U . . . C1E C 0.4316(2) -0.03122(18) 0.70020(18) 0.0749(5) Uani 1 1 d . . . . . H1E H 0.440404 -0.086150 0.650527 0.090 Uiso 1 1 calc R U . . . C1F C 0.5447(2) 0.0232(2) 0.71489(19) 0.0774(5) Uani 1 1 d . . . . . H1F H 0.629730 0.006557 0.673602 0.093 Uiso 1 1 calc R U . . . O1 O 0.21270(14) 0.40447(10) 0.75230(10) 0.0668(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 O2 0.0662(7) 0.0548(6) 0.0626(6) -0.0193(5) 0.0081(5) -0.0232(5) O3 0.0555(6) 0.0745(7) 0.0926(9) -0.0440(7) 0.0034(6) -0.0242(5) N6 0.0670(7) 0.0373(5) 0.0335(5) -0.0169(4) -0.0054(5) -0.0026(5) N5 0.0636(7) 0.0421(6) 0.0385(5) -0.0217(5) -0.0045(5) -0.0034(5) C20 0.0485(7) 0.0468(7) 0.0378(6) -0.0206(5) -0.0019(5) -0.0062(5) C2 0.0539(8) 0.0439(7) 0.0325(6) -0.0153(5) -0.0021(5) -0.0026(5) C3 0.0505(7) 0.0453(7) 0.0354(6) -0.0132(5) -0.0043(5) -0.0040(5) C4 0.0523(7) 0.0442(7) 0.0355(6) -0.0163(5) -0.0036(5) -0.0085(5) C6 0.0522(8) 0.0446(7) 0.0389(6) -0.0109(5) -0.0071(5) -0.0100(6) C5 0.0610(8) 0.0409(7) 0.0372(6) -0.0161(5) -0.0078(6) -0.0040(6) C7 0.0538(8) 0.0383(6) 0.0448(7) -0.0110(5) -0.0073(6) -0.0026(5) C8 0.0473(7) 0.0461(7) 0.0378(6) -0.0142(5) -0.0021(5) -0.0101(5) C9 0.0499(8) 0.0428(7) 0.0483(7) -0.0122(6) -0.0063(6) -0.0097(6) C10 0.0701(10) 0.0643(9) 0.0448(7) -0.0325(7) -0.0063(7) -0.0019(7) C11 0.0784(10) 0.0445(7) 0.0437(7) -0.0157(6) -0.0060(7) -0.0110(7) C12 0.0656(10) 0.0728(10) 0.0440(7) -0.0214(7) -0.0004(7) -0.0224(8) C13 0.0893(12) 0.0730(11) 0.0328(7) -0.0129(7) -0.0053(7) -0.0046(9) C14 0.0595(9) 0.0578(8) 0.0427(7) -0.0124(6) -0.0001(6) -0.0108(7) C15 0.0842(12) 0.0848(12) 0.0391(8) -0.0235(8) -0.0151(8) 0.0048(9) C16 0.0640(9) 0.0618(9) 0.0655(9) -0.0304(8) 0.0002(7) -0.0172(7) C17 0.161(2) 0.0732(12) 0.0392(8) -0.0289(8) -0.0128(10) -0.0091(12) C18 0.0844(11) 0.0504(8) 0.0450(8) -0.0048(6) -0.0052(7) -0.0085(8) C19 0.1375(17) 0.0495(8) 0.0399(8) -0.0210(7) -0.0117(9) -0.0037(9) C1A 0.0809(11) 0.0730(11) 0.0373(7) -0.0093(7) 0.0022(7) -0.0084(9) C1B 0.0751(11) 0.0922(13) 0.0575(9) -0.0351(9) -0.0133(8) -0.0174(9) C1C 0.0941(13) 0.0625(10) 0.0698(10) -0.0309(9) -0.0101(9) -0.0217(9) C1D 0.0565(9) 0.0656(10) 0.0662(10) -0.0261(8) -0.0052(7) -0.0027(7) C1E 0.1048(15) 0.0565(9) 0.0652(10) -0.0312(8) -0.0138(10) 0.0077(9) C1F 0.0756(12) 0.0833(12) 0.0739(12) -0.0397(10) -0.0026(9) 0.0109(9) O1 0.1122(9) 0.0404(5) 0.0506(6) -0.0223(5) -0.0242(6) 0.0030(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 N5 N6 C2 118.89(10) . . ? C5 N6 N5 111.79(10) . . ? C5 N6 C2 129.27(10) . . ? C20 N5 N6 108.33(10) . . ? N5 C20 C4 110.98(10) . . ? N5 C20 C10 120.05(12) . . ? C4 C20 C10 128.82(12) . . ? C11 C2 N6 120.07(11) . . ? C11 C2 C19 119.59(12) . . ? C19 C2 N6 120.33(12) . . ? C12 C3 C8 120.06(12) . . ? C12 C3 C14 118.94(12) . . ? C14 C3 C8 120.98(12) . . ? C20 C4 C5 104.04(10) . . ? C8 C4 C20 134.31(12) . . ? C8 C4 C5 121.65(12) . . ? O2 C6 C8 120.79(13) . . ? O2 C6 C9 123.99(12) . . ? C8 C6 C9 114.73(11) . . ? N6 C5 C4 104.72(10) . . ? O1 C5 N6 127.90(12) . . ? O1 C5 C4 127.38(12) . . ? C16 C7 C9 123.31(13) . . ? C16 C7 C1D 118.87(14) . . ? C1D C7 C9 117.79(13) . . ? C3 C8 C6 115.86(11) . . ? C4 C8 C3 125.95(12) . . ? C4 C8 C6 118.19(11) . . ? O3 C9 C6 114.78(12) . . ? O3 C9 C7 123.40(13) . . ? C7 C9 C6 121.78(11) . . ? C20 C10 H10A 109.5 . . ? C20 C10 H10B 109.5 . . ? C20 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C2 C11 H11 120.2 . . ? C2 C11 C18 119.60(13) . . ? C18 C11 H11 120.2 . . ? C3 C12 H12 119.9 . . ? C1B C12 C3 120.15(15) . . ? C1B C12 H12 119.9 . . ? C17 C13 H13 120.5 . . ? C18 C13 H13 120.5 . . ? C18 C13 C17 119.04(14) . . ? C3 C14 H14 119.9 . . ? C1A C14 C3 120.24(15) . . ? C1A C14 H14 119.9 . . ? C1A C15 H15 120.1 . . ? C1A C15 C1B 119.75(14) . . ? C1B C15 H15 120.1 . . ? C7 C16 H16 120.0 . . ? C7 C16 C1C 120.06(16) . . ? C1C C16 H16 120.0 . . ? C13 C17 H17 119.3 . . ? C13 C17 C19 121.35(16) . . ? C19 C17 H17 119.3 . . ? C11 C18 H18 119.4 . . ? C13 C18 C11 121.11(14) . . ? C13 C18 H18 119.4 . . ? C2 C19 C17 119.30(15) . . ? C2 C19 H19 120.4 . . ? C17 C19 H19 120.4 . . ? C14 C1A H1A 119.7 . . ? C15 C1A C14 120.63(15) . . ? C15 C1A H1A 119.7 . . ? C12 C1B H1B 119.9 . . ? C15 C1B C12 120.28(16) . . ? C15 C1B H1B 119.9 . . ? C16 C1C H1C 119.8 . . ? C1E C1C C16 120.39(17) . . ? C1E C1C H1C 119.8 . . ? C7 C1D H1D 119.8 . . ? C1F C1D C7 120.33(16) . . ? C1F C1D H1D 119.8 . . ? C1C C1E H1E 120.0 . . ? C1F C1E C1C 119.99(16) . . ? C1F C1E H1E 120.0 . . ? C1D C1F H1F 119.8 . . ? C1E C1F C1D 120.34(17) . . ? C1E C1F H1F 119.8 . . ? 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 O2 C6 1.2025(16) . ? O3 C9 1.2199(16) . ? N6 N5 1.4126(14) . ? N6 C2 1.4197(16) . ? N6 C5 1.3674(16) . ? N5 C20 1.2943(16) . ? C20 C4 1.4650(18) . ? C20 C10 1.4933(17) . ? C2 C11 1.3789(19) . ? C2 C19 1.3825(19) . ? C3 C8 1.4862(17) . ? C3 C12 1.388(2) . ? C3 C14 1.3913(19) . ? C4 C5 1.4891(17) . ? C4 C8 1.3453(18) . ? C6 C8 1.5304(18) . ? C6 C9 1.538(2) . ? C5 O1 1.2232(15) . ? C7 C9 1.4834(19) . ? C7 C16 1.385(2) . ? C7 C1D 1.391(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11 0.9300 . ? C11 C18 1.391(2) . ? C12 H12 0.9300 . ? C12 C1B 1.387(2) . ? C13 H13 0.9300 . ? C13 C17 1.369(3) . ? C13 C18 1.358(2) . ? C14 H14 0.9300 . ? C14 C1A 1.382(2) . ? C15 H15 0.9300 . ? C15 C1A 1.369(3) . ? C15 C1B 1.381(3) . ? C16 H16 0.9300 . ? C16 C1C 1.386(2) . ? C17 H17 0.9300 . ? C17 C19 1.385(2) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C1A H1A 0.9300 . ? C1B H1B 0.9300 . ? C1C H1C 0.9300 . ? C1C C1E 1.371(3) . ? C1D H1D 0.9300 . ? C1D C1F 1.380(2) . ? C1E H1E 0.9300 . ? C1E C1F 1.368(3) . ? C1F H1F 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 O2 C6 C8 C3 68.16(17) . . . . ? O2 C6 C8 C4 -111.98(15) . . . . ? O2 C6 C9 O3 -144.99(14) . . . . ? O2 C6 C9 C7 32.94(19) . . . . ? N6 N5 C20 C4 -0.46(15) . . . . ? N6 N5 C20 C10 -176.34(12) . . . . ? N6 C2 C11 C18 -179.11(14) . . . . ? N6 C2 C19 C17 178.98(18) . . . . ? N5 N6 C2 C11 11.06(19) . . . . ? N5 N6 C2 C19 -167.53(14) . . . . ? N5 N6 C5 C4 -3.98(15) . . . . ? N5 N6 C5 O1 176.43(15) . . . . ? N5 C20 C4 C5 -1.89(15) . . . . ? N5 C20 C4 C8 179.04(15) . . . . ? C20 C4 C5 N6 3.47(14) . . . . ? C20 C4 C5 O1 -176.95(15) . . . . ? C20 C4 C8 C3 -7.4(3) . . . . ? C20 C4 C8 C6 172.76(14) . . . . ? C2 N6 N5 C20 -179.46(12) . . . . ? C2 N6 C5 C4 178.74(13) . . . . ? C2 N6 C5 O1 -0.8(3) . . . . ? C2 C11 C18 C13 -0.2(3) . . . . ? C3 C12 C1B C15 -0.6(3) . . . . ? C3 C14 C1A C15 -1.5(3) . . . . ? C5 N6 N5 C20 2.95(16) . . . . ? C5 N6 C2 C11 -171.83(14) . . . . ? C5 N6 C2 C19 9.6(2) . . . . ? C5 C4 C8 C3 173.67(12) . . . . ? C5 C4 C8 C6 -6.18(19) . . . . ? C7 C16 C1C C1E -0.6(3) . . . . ? C7 C1D C1F C1E -0.5(3) . . . . ? C8 C3 C12 C1B -178.21(15) . . . . ? C8 C3 C14 C1A 179.24(14) . . . . ? C8 C4 C5 N6 -177.32(12) . . . . ? C8 C4 C5 O1 2.3(2) . . . . ? C8 C6 C9 O3 26.95(17) . . . . ? C8 C6 C9 C7 -155.11(11) . . . . ? C9 C6 C8 C3 -104.07(13) . . . . ? C9 C6 C8 C4 75.79(15) . . . . ? C9 C7 C16 C1C 179.02(14) . . . . ? C9 C7 C1D C1F -178.62(14) . . . . ? C10 C20 C4 C5 173.53(14) . . . . ? C10 C20 C4 C8 -5.5(3) . . . . ? C11 C2 C19 C17 0.4(3) . . . . ? C12 C3 C8 C4 -58.7(2) . . . . ? C12 C3 C8 C6 121.17(15) . . . . ? C12 C3 C14 C1A 0.7(2) . . . . ? C13 C17 C19 C2 0.5(3) . . . . ? C14 C3 C8 C4 122.81(16) . . . . ? C14 C3 C8 C6 -57.34(17) . . . . ? C14 C3 C12 C1B 0.3(2) . . . . ? C16 C7 C9 O3 -176.26(14) . . . . ? C16 C7 C9 C6 6.0(2) . . . . ? C16 C7 C1D C1F -0.8(2) . . . . ? C16 C1C C1E C1F -0.7(3) . . . . ? C17 C13 C18 C11 1.0(3) . . . . ? C18 C13 C17 C19 -1.1(3) . . . . ? C19 C2 C11 C18 -0.5(2) . . . . ? C1A C15 C1B C12 -0.2(3) . . . . ? C1B C15 C1A C14 1.2(3) . . . . ? C1C C1E C1F C1D 1.3(3) . . . . ? C1D C7 C9 O3 1.5(2) . . . . ? C1D C7 C9 C6 -176.29(12) . . . . ? C1D C7 C16 C1C 1.3(2) . . . . ?