#------------------------------------------------------------------------------ #$Date: 2016-05-12 09:31:33 +0300 (Thu, 12 May 2016) $ #$Revision: 182904 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225218.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_7225218 loop_ _publ_author_name 'Cacciarini, Martina' 'Jevric, Martyn' 'Elm, Jonas' 'Petersen, Anne U.' 'Mikkelsen, Kurt V.' 'Nielsen, Mogens Brondsted' _publ_section_title ; Fine-tuning the lifetimes and energy storage capacities of meta-stable vinylheptafulvenes via substitution at the vinyl position ; _journal_name_full 'RSC Adv.' _journal_paper_doi 10.1039/C6RA06045E _journal_year 2016 _chemical_formula_moiety 'C24 H18 N2 O, C3 H6 O' _chemical_formula_sum 'C27 H24 N2 O2' _chemical_formula_weight 408.4988 _chemical_melting_point 193.5(15) _chemical_name_systematic '(1S,8aR or 1R,8aS)-1-cyano-2,3-diphenyl-1,8a-dihydroazulene-1-carboxamide' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2016-02-19 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2016-02-19 deposited with the CCDC. 2016-05-10 downloaded from the CCDC. ; _cell_angle_alpha 99.022(3) _cell_angle_beta 106.294(3) _cell_angle_gamma 98.866(3) _cell_formula_units_Z 2 _cell_length_a 9.0724(7) _cell_length_b 11.2010(8) _cell_length_c 11.4779(8) _cell_measurement_reflns_used 9989 _cell_measurement_temperature 122 _cell_measurement_theta_max 32.81 _cell_measurement_theta_min 2.54 _cell_volume 1081.27(14) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _diffrn_ambient_temperature 122 _diffrn_measured_fraction_theta_full 0.899 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_unetI/netI 0.0266 _diffrn_reflns_Laue_measured_fraction_full 0.899 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 21261 _diffrn_reflns_point_group_measured_fraction_full 0.899 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 25.026 _diffrn_reflns_theta_min 2.370 _diffrn_source 'sealed X-ray tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max 0.7466 _exptl_absorpt_correction_T_min 0.6959 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0934 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.9321. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.255 _exptl_crystal_description prism _exptl_crystal_F_000 432 _exptl_crystal_size_max 0.670 _exptl_crystal_size_mid 0.346 _exptl_crystal_size_min 0.189 _refine_diff_density_max 0.233 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 354 _refine_ls_number_reflns 3826 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0368 _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^)+(0.0469P)^2^+0.4398P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0916 _refine_ls_wR_factor_ref 0.0969 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3319 _reflns_number_total 3826 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ra06045e2.cif _cod_data_source_block mo_d8v1282_0ma _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '192-195' was changed to '193.5(15)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas ; _cod_database_code 7225218 _shelxl_version_number 2014/6 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.5 times of: All C(H,H,H) groups 2.a Idealised Me refined as rotating group: C30(H30A,H30B,H30C), C31(H31A,H31B,H31C) ; _shelx_res_file ; TITL mo_D8V1282_0ma in P-1 #2 REM reset to P-1 #2 CELL 0.71073 9.0724 11.201 11.4779 99.022 106.2937 98.8663 ZERR 2 0.0007 0.0008 0.0008 0.0026 0.0026 0.0027 LATT 1 SFAC C H N O UNIT 48 36 4 2 L.S. 8 0 0 PLAN 20 TEMP 0 BOND MORE -1 BOND $H CONF fmap 2 53 acta 52 REM REM REM WGHT 0.046900 0.439800 FVAR 0.26598 O1 4 0.364184 0.427493 0.343738 11.00000 0.02566 0.01476 = 0.02375 0.00570 0.00169 0.00858 N2 3 0.417778 0.628933 0.438330 11.00000 0.01967 0.01434 = 0.01847 0.00423 0.00161 0.00685 N4 3 0.137649 0.382667 0.044115 11.00000 0.03233 0.02117 = 0.02196 0.00200 0.00724 0.00301 C5 1 0.139330 0.755707 0.248587 11.00000 0.01490 0.01529 = 0.01514 0.00319 0.00023 0.00192 C6 1 0.168876 0.457749 0.132107 11.00000 0.01804 0.01525 = 0.01982 0.00854 0.00537 0.00401 C7 1 0.202743 0.556990 0.243009 11.00000 0.01646 0.01338 = 0.01559 0.00402 0.00389 0.00362 C8 1 0.040601 0.689062 0.307638 11.00000 0.01521 0.01796 = 0.01768 0.00519 0.00113 0.00457 C9 1 0.466107 0.651824 0.144410 11.00000 0.02189 0.02131 = 0.02313 0.00924 0.00671 0.00533 C10 1 0.127730 0.884229 0.234326 11.00000 0.02140 0.01460 = 0.01923 0.00409 0.00748 0.00563 C11 1 0.339655 0.532686 0.346931 11.00000 0.01438 0.01565 = 0.01638 0.00641 0.00638 0.00448 C12 1 0.341509 0.712854 0.139586 11.00000 0.01706 0.01502 = 0.01537 0.00187 0.00161 0.00028 C13 1 0.231431 0.684675 0.209543 11.00000 0.01477 0.01308 = 0.01458 0.00408 -0.00043 0.00200 C14 1 0.553383 0.766742 0.007554 11.00000 0.02447 0.03187 = 0.02272 0.00627 0.00955 -0.00156 C15 1 0.059019 0.556828 0.294251 11.00000 0.01657 0.01694 = 0.01865 0.00712 0.00526 0.00475 C16 1 0.570303 0.678368 0.079575 11.00000 0.02064 0.03201 = 0.02701 0.00814 0.00871 0.00651 C17 1 0.429581 0.827278 0.000676 11.00000 0.03458 0.02435 = 0.02265 0.01129 0.00835 0.00289 C18 1 -0.013814 0.904424 0.162365 11.00000 0.02405 0.02078 = 0.02840 0.00832 0.00566 0.00797 C19 1 0.324130 0.800371 0.064453 11.00000 0.02610 0.02184 = 0.02096 0.00711 0.00547 0.00760 C20 1 -0.096736 0.477942 0.213007 11.00000 0.02005 0.01888 = 0.02593 0.00730 0.00340 0.00165 C21 1 0.252765 0.984385 0.291178 11.00000 0.02778 0.01887 = 0.03155 0.00326 0.00379 0.00215 C22 1 -0.028303 1.022614 0.145955 11.00000 0.04075 0.02968 = 0.03861 0.01741 0.01123 0.01984 C23 1 -0.222303 0.470393 0.252673 11.00000 0.01821 0.02682 = 0.03712 0.01402 0.00503 0.00164 C24 1 -0.155210 0.659984 0.418651 11.00000 0.02724 0.03696 = 0.03507 0.01454 0.01783 0.01580 C25 1 -0.050134 0.734323 0.371276 11.00000 0.02559 0.02257 = 0.02993 0.00885 0.01085 0.01059 C26 1 -0.230435 0.541997 0.366263 11.00000 0.02119 0.03707 = 0.04035 0.02229 0.01550 0.01117 C27 1 0.236748 1.102464 0.274268 11.00000 0.04453 0.01631 = 0.04296 0.00363 0.01172 -0.00080 C28 1 0.097163 1.121590 0.201626 11.00000 0.05918 0.01693 = 0.04323 0.01423 0.02369 0.01526 O3 4 0.386803 0.874109 0.527075 11.00000 0.03585 0.02418 = 0.03986 -0.00381 0.00370 0.00795 C29 1 0.318341 0.902936 0.600543 11.00000 0.03637 0.03050 = 0.02704 -0.00269 -0.00312 0.00906 C30 1 0.308031 1.034483 0.637280 11.00000 0.06687 0.04376 = 0.09074 -0.01057 0.02518 0.02633 AFIX 137 H30A 2 0.368157 1.066105 0.723032 11.00000 -1.50000 H30B 2 0.200297 1.039351 0.625642 11.00000 -1.50000 H30C 2 0.349009 1.082609 0.586797 11.00000 -1.50000 AFIX 0 C31 1 0.246756 0.808664 0.656810 11.00000 0.11795 0.05740 = 0.03539 0.00961 0.02821 0.00709 AFIX 137 H31A 2 0.229279 0.728184 0.605505 11.00000 -1.50000 H31B 2 0.148422 0.825352 0.663431 11.00000 -1.50000 H31C 2 0.316147 0.811325 0.737980 11.00000 -1.50000 AFIX 0 H15 2 0.081247 0.530534 0.375477 11.00000 0.02147 H20 2 -0.102792 0.431372 0.130510 11.00000 0.03231 H9 2 0.482850 0.591018 0.196216 11.00000 0.02635 H18 2 -0.097596 0.836441 0.124417 11.00000 0.02963 H19 2 0.232728 0.839951 0.053843 11.00000 0.02431 H17 2 0.414240 0.888954 -0.048282 11.00000 0.03247 H21 2 0.351877 0.971167 0.344683 11.00000 0.04182 H25 2 -0.047365 0.822536 0.383583 11.00000 0.02838 H14 2 0.626406 0.783418 -0.038957 11.00000 0.03026 H16 2 0.653296 0.633271 0.083514 11.00000 0.03951 H2A 2 0.393868 0.700917 0.440302 11.00000 0.02566 H2B 2 0.488222 0.615112 0.502935 11.00000 0.02585 H23 2 -0.319777 0.411993 0.199866 11.00000 0.03618 H24 2 -0.180845 0.702749 0.490501 11.00000 0.03963 H28 2 0.087371 1.202402 0.190264 11.00000 0.04619 H22 2 -0.130430 1.032863 0.094243 11.00000 0.04850 H26 2 -0.307889 0.506022 0.399858 11.00000 0.03705 H27 2 0.326323 1.171113 0.312891 11.00000 0.05406 HKLF 4 REM mo_D8V1282_0ma in P-1 #2 REM R1 = 0.0368 for 3319 Fo > 4sig(Fo) and 0.0439 for all 3826 data REM 354 parameters refined using 0 restraints END WGHT 0.0469 0.4397 REM Highest difference peak 0.233, deepest hole -0.220, 1-sigma level 0.040 Q1 1 0.2902 1.0647 0.5591 11.00000 0.05 0.23 Q2 1 0.2699 0.5420 0.2903 11.00000 0.05 0.22 Q3 1 0.2259 0.6202 0.2243 11.00000 0.05 0.21 Q4 1 0.0503 0.6263 0.3063 11.00000 0.05 0.20 Q5 1 0.2279 0.8234 0.7428 11.00000 0.05 0.18 Q6 1 0.1268 0.5509 0.2611 11.00000 0.05 0.18 Q7 1 0.2131 0.9940 0.6037 11.00000 0.05 0.17 Q8 1 -0.0912 0.4614 0.3916 11.00000 0.05 0.17 Q9 1 0.2421 1.0450 0.7145 11.00000 0.05 0.16 Q10 1 0.2525 1.0401 0.2355 11.00000 0.05 0.16 Q11 1 0.0398 0.7184 0.3802 11.00000 0.05 0.16 Q12 1 0.1908 0.8872 0.6646 11.00000 0.05 0.15 Q13 1 0.3721 0.8598 0.7005 11.00000 0.05 0.15 Q14 1 0.2661 0.6834 0.1565 11.00000 0.05 0.15 Q15 1 0.1067 0.7343 0.2972 11.00000 0.05 0.14 Q16 1 0.2013 0.9198 0.2270 11.00000 0.05 0.14 Q17 1 0.0105 0.4600 0.3378 11.00000 0.05 0.14 Q18 1 0.1369 0.8224 0.2418 11.00000 0.05 0.13 Q19 1 -0.0153 0.5188 0.2481 11.00000 0.05 0.13 Q20 1 0.2389 0.7401 0.2718 11.00000 0.05 0.13 ; _shelx_res_checksum 15258 _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 O1 O 0.36418(11) 0.42749(8) 0.34374(9) 0.0220(2) Uani 1 1 d . N2 N 0.41778(13) 0.62893(11) 0.43833(11) 0.0180(2) Uani 1 1 d . N4 N 0.13765(15) 0.38267(11) 0.04411(11) 0.0260(3) Uani 1 1 d . C5 C 0.13933(15) 0.75571(12) 0.24859(12) 0.0162(3) Uani 1 1 d . C6 C 0.16888(15) 0.45775(12) 0.13211(12) 0.0172(3) Uani 1 1 d . C7 C 0.20274(15) 0.55699(11) 0.24301(11) 0.0152(3) Uani 1 1 d . C8 C 0.04060(15) 0.68906(12) 0.30764(12) 0.0175(3) Uani 1 1 d . C9 C 0.46611(16) 0.65182(13) 0.14441(13) 0.0216(3) Uani 1 1 d . C10 C 0.12773(16) 0.88423(12) 0.23433(12) 0.0179(3) Uani 1 1 d . C11 C 0.33966(14) 0.53269(11) 0.34693(12) 0.0146(3) Uani 1 1 d . C12 C 0.34151(15) 0.71285(12) 0.13959(12) 0.0171(3) Uani 1 1 d . C13 C 0.23143(15) 0.68467(11) 0.20954(11) 0.0152(3) Uani 1 1 d . C14 C 0.55338(17) 0.76674(14) 0.00755(13) 0.0267(3) Uani 1 1 d . C15 C 0.05902(15) 0.55683(12) 0.29425(12) 0.0169(3) Uani 1 1 d . C16 C 0.57030(17) 0.67837(14) 0.07957(14) 0.0259(3) Uani 1 1 d . C17 C 0.42958(18) 0.82728(14) 0.00068(14) 0.0270(3) Uani 1 1 d . C18 C -0.01381(18) 0.90442(14) 0.16237(14) 0.0242(3) Uani 1 1 d . C19 C 0.32413(17) 0.80037(13) 0.06445(13) 0.0228(3) Uani 1 1 d . C20 C -0.09674(16) 0.47794(13) 0.21301(14) 0.0224(3) Uani 1 1 d . C21 C 0.25276(18) 0.98438(13) 0.29118(15) 0.0278(3) Uani 1 1 d . C22 C -0.0283(2) 1.02261(15) 0.14596(16) 0.0340(4) Uani 1 1 d . C23 C -0.22230(17) 0.47039(14) 0.25267(15) 0.0277(3) Uani 1 1 d . C24 C -0.15521(18) 0.65998(15) 0.41865(15) 0.0295(4) Uani 1 1 d . C25 C -0.05013(17) 0.73432(14) 0.37128(14) 0.0246(3) Uani 1 1 d . C26 C -0.23043(17) 0.54200(15) 0.36626(15) 0.0294(4) Uani 1 1 d . C27 C 0.2367(2) 1.10246(14) 0.27427(17) 0.0361(4) Uani 1 1 d . C28 C 0.0972(2) 1.12159(14) 0.20163(16) 0.0364(4) Uani 1 1 d . O3 O 0.38680(13) 0.87411(10) 0.52707(11) 0.0360(3) Uani 1 1 d . C29 C 0.3183(2) 0.90294(15) 0.60054(15) 0.0348(4) Uani 1 1 d . C30 C 0.3080(3) 1.0345(2) 0.6373(3) 0.0682(7) Uani 1 1 d . H30A H 0.3682 1.0661 0.7230 0.102 Uiso 1 1 calc GR H30B H 0.2003 1.0394 0.6256 0.102 Uiso 1 1 calc GR H30C H 0.3490 1.0826 0.5868 0.102 Uiso 1 1 calc GR C31 C 0.2468(4) 0.8087(2) 0.6568(2) 0.0706(7) Uani 1 1 d . H31A H 0.2293 0.7282 0.6055 0.106 Uiso 1 1 calc GR H31B H 0.1484 0.8254 0.6634 0.106 Uiso 1 1 calc GR H31C H 0.3161 0.8113 0.7380 0.106 Uiso 1 1 calc GR H15 H 0.0812(18) 0.5305(14) 0.3755(15) 0.021(4) Uiso 1 1 d . H20 H -0.103(2) 0.4314(16) 0.1305(17) 0.032(4) Uiso 1 1 d . H9 H 0.4829(19) 0.5910(15) 0.1962(15) 0.026(4) Uiso 1 1 d . H18 H -0.098(2) 0.8364(16) 0.1244(15) 0.030(4) Uiso 1 1 d . H19 H 0.2327(19) 0.8400(14) 0.0538(14) 0.024(4) Uiso 1 1 d . H17 H 0.414(2) 0.8890(16) -0.0483(16) 0.032(4) Uiso 1 1 d . H21 H 0.352(2) 0.9712(17) 0.3447(17) 0.042(5) Uiso 1 1 d . H25 H -0.0474(19) 0.8225(16) 0.3836(15) 0.028(4) Uiso 1 1 d . H14 H 0.626(2) 0.7834(15) -0.0390(15) 0.030(4) Uiso 1 1 d . H16 H 0.653(2) 0.6333(17) 0.0835(17) 0.040(5) Uiso 1 1 d . H2A H 0.3939(19) 0.7009(16) 0.4403(15) 0.026(4) Uiso 1 1 d . H2B H 0.488(2) 0.6151(15) 0.5029(16) 0.026(4) Uiso 1 1 d . H23 H -0.320(2) 0.4120(16) 0.1999(16) 0.036(5) Uiso 1 1 d . H24 H -0.181(2) 0.7027(17) 0.4905(18) 0.040(5) Uiso 1 1 d . H28 H 0.087(2) 1.2024(18) 0.1903(18) 0.046(5) Uiso 1 1 d . H22 H -0.130(2) 1.0329(18) 0.0942(19) 0.048(5) Uiso 1 1 d . H26 H -0.308(2) 0.5060(16) 0.3999(16) 0.037(5) Uiso 1 1 d . H27 H 0.326(3) 1.171(2) 0.3129(19) 0.054(6) 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 0.0257(5) 0.0148(5) 0.0237(5) 0.0057(4) 0.0017(4) 0.0086(4) N2 0.0197(6) 0.0143(6) 0.0185(6) 0.0042(5) 0.0016(5) 0.0068(5) N4 0.0323(7) 0.0212(6) 0.0220(6) 0.0020(5) 0.0072(5) 0.0030(5) C5 0.0149(6) 0.0153(6) 0.0151(6) 0.0032(5) 0.0002(5) 0.0019(5) C6 0.0180(7) 0.0153(6) 0.0198(7) 0.0085(6) 0.0054(5) 0.0040(5) C7 0.0165(6) 0.0134(6) 0.0156(6) 0.0040(5) 0.0039(5) 0.0036(5) C8 0.0152(6) 0.0180(7) 0.0177(6) 0.0052(5) 0.0011(5) 0.0046(5) C9 0.0219(7) 0.0213(7) 0.0231(7) 0.0092(6) 0.0067(6) 0.0053(6) C10 0.0214(7) 0.0146(6) 0.0192(7) 0.0041(5) 0.0075(5) 0.0056(5) C11 0.0144(6) 0.0157(6) 0.0164(6) 0.0064(5) 0.0064(5) 0.0045(5) C12 0.0171(6) 0.0150(6) 0.0154(6) 0.0019(5) 0.0016(5) 0.0003(5) C13 0.0148(6) 0.0131(6) 0.0146(6) 0.0041(5) -0.0004(5) 0.0020(5) C14 0.0245(8) 0.0319(8) 0.0227(7) 0.0063(6) 0.0095(6) -0.0016(6) C15 0.0166(7) 0.0169(7) 0.0187(7) 0.0071(5) 0.0053(5) 0.0048(5) C16 0.0206(7) 0.0320(8) 0.0270(8) 0.0081(6) 0.0087(6) 0.0065(6) C17 0.0346(8) 0.0243(7) 0.0227(7) 0.0113(6) 0.0084(6) 0.0029(6) C18 0.0240(8) 0.0208(7) 0.0284(8) 0.0083(6) 0.0057(6) 0.0080(6) C19 0.0261(8) 0.0218(7) 0.0210(7) 0.0071(6) 0.0055(6) 0.0076(6) C20 0.0200(7) 0.0189(7) 0.0259(8) 0.0073(6) 0.0034(6) 0.0017(5) C21 0.0278(8) 0.0189(7) 0.0315(8) 0.0033(6) 0.0038(7) 0.0021(6) C22 0.0408(10) 0.0297(9) 0.0386(9) 0.0174(7) 0.0112(8) 0.0198(7) C23 0.0182(7) 0.0268(8) 0.0371(9) 0.0140(7) 0.0050(6) 0.0016(6) C24 0.0272(8) 0.0370(9) 0.0351(9) 0.0145(7) 0.0178(7) 0.0158(7) C25 0.0256(8) 0.0226(8) 0.0299(8) 0.0088(6) 0.0109(6) 0.0106(6) C26 0.0212(7) 0.0371(9) 0.0403(9) 0.0223(7) 0.0155(7) 0.0112(7) C27 0.0445(10) 0.0163(8) 0.0430(10) 0.0036(7) 0.0117(8) -0.0008(7) C28 0.0592(11) 0.0169(8) 0.0432(10) 0.0142(7) 0.0237(9) 0.0153(7) O3 0.0358(6) 0.0242(6) 0.0399(7) -0.0038(5) 0.0037(5) 0.0080(5) C29 0.0364(9) 0.0305(9) 0.0270(8) -0.0027(7) -0.0031(7) 0.0091(7) C30 0.0669(15) 0.0438(12) 0.0907(17) -0.0106(11) 0.0252(13) 0.0263(11) C31 0.118(2) 0.0574(14) 0.0354(11) 0.0096(10) 0.0282(13) 0.0071(14) 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 C11 N2 H2A 122.1(11) C11 N2 H2B 117.4(10) H2A N2 H2B 120.1(15) C8 C5 C10 120.46(11) C13 C5 C8 111.18(11) C13 C5 C10 128.34(12) N4 C6 C7 177.33(14) C6 C7 C11 107.69(10) C6 C7 C13 110.31(10) C6 C7 C15 112.31(10) C11 C7 C15 107.01(10) C13 C7 C11 115.33(10) C13 C7 C15 104.23(10) C5 C8 C15 109.66(11) C25 C8 C5 127.80(12) C25 C8 C15 122.48(12) C12 C9 H9 120.1(9) C16 C9 C12 121.44(13) C16 C9 H9 118.5(9) C18 C10 C5 118.63(12) C21 C10 C5 122.32(12) C21 C10 C18 119.05(13) O1 C11 N2 124.26(12) O1 C11 C7 119.67(11) N2 C11 C7 115.96(11) C9 C12 C13 121.17(12) C9 C12 C19 117.55(12) C19 C12 C13 121.28(12) C5 C13 C7 110.33(11) C5 C13 C12 129.14(12) C12 C13 C7 120.48(11) C16 C14 C17 118.99(14) C16 C14 H14 119.5(10) C17 C14 H14 121.5(10) C7 C15 H15 111.0(9) C8 C15 C7 103.44(10) C8 C15 H15 111.7(9) C20 C15 C7 117.43(11) C20 C15 C8 106.97(10) C20 C15 H15 106.3(9) C9 C16 C14 120.36(14) C9 C16 H16 119.2(11) C14 C16 H16 120.4(11) C14 C17 H17 121.3(10) C19 C17 C14 120.93(13) C19 C17 H17 117.8(10) C10 C18 H18 118.5(10) C22 C18 C10 120.19(14) C22 C18 H18 121.3(10) C12 C19 H19 119.4(9) C17 C19 C12 120.71(13) C17 C19 H19 119.8(9) C15 C20 H20 118.2(10) C23 C20 C15 120.47(14) C23 C20 H20 121.3(10) C10 C21 H21 119.4(11) C27 C21 C10 120.23(15) C27 C21 H21 120.3(11) C18 C22 H22 117.6(11) C28 C22 C18 120.43(15) C28 C22 H22 122.0(11) C20 C23 C26 125.98(14) C20 C23 H23 118.0(10) C26 C23 H23 116.0(10) C25 C24 H24 116.3(11) C26 C24 C25 125.12(15) C26 C24 H24 118.3(11) C8 C25 C24 124.45(14) C8 C25 H25 117.8(10) C24 C25 H25 117.8(10) C23 C26 H26 116.2(11) C24 C26 C23 125.83(14) C24 C26 H26 117.3(11) C21 C27 H27 119.1(12) C28 C27 C21 120.44(15) C28 C27 H27 120.4(12) C22 C28 H28 120.5(12) C27 C28 C22 119.64(14) C27 C28 H28 119.9(12) O3 C29 C30 120.34(18) O3 C29 C31 120.50(17) C31 C29 C30 119.15(19) C29 C30 H30A 109.5 C29 C30 H30B 109.5 C29 C30 H30C 109.5 H30A C30 H30B 109.5 H30A C30 H30C 109.5 H30B C30 H30C 109.5 C29 C31 H31A 109.5 C29 C31 H31B 109.5 C29 C31 H31C 109.5 H31A C31 H31B 109.5 H31A C31 H31C 109.5 H31B C31 H31C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C11 1.2292(15) N2 C11 1.3258(17) N2 H2A 0.865(18) N2 H2B 0.885(18) N4 C6 1.1433(18) C5 C8 1.4533(18) C5 C10 1.4904(17) C5 C13 1.3547(18) C6 C7 1.4771(18) C7 C11 1.5539(17) C7 C13 1.5409(17) C7 C15 1.5736(18) C8 C15 1.5049(18) C8 C25 1.348(2) C9 C12 1.4011(19) C9 C16 1.383(2) C9 H9 0.974(16) C10 C18 1.391(2) C10 C21 1.391(2) C12 C13 1.4744(18) C12 C19 1.4021(19) C14 C16 1.385(2) C14 C17 1.389(2) C14 H14 0.975(18) C15 C20 1.5048(19) C15 H15 0.998(16) C16 H16 0.964(19) C17 C19 1.384(2) C17 H17 0.959(17) C18 C22 1.387(2) C18 H18 0.938(18) C19 H19 0.986(16) C20 C23 1.336(2) C20 H20 0.989(18) C21 C27 1.390(2) C21 H21 0.98(2) C22 C28 1.383(3) C22 H22 0.98(2) C23 C26 1.447(2) C23 H23 0.987(19) C24 C25 1.444(2) C24 C26 1.348(2) C24 H24 0.991(19) C25 H25 0.971(17) C26 H26 0.958(19) C27 C28 1.375(3) C27 H27 0.97(2) C28 H28 0.95(2) O3 C29 1.213(2) C29 C30 1.492(2) C29 C31 1.480(3) C30 H30A 0.9600 C30 H30B 0.9600 C30 H30C 0.9600 C31 H31A 0.9600 C31 H31B 0.9600 C31 H31C 0.9600 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 C5 C8 C15 C7 10.25(13) C5 C8 C15 C20 -114.38(12) C5 C8 C25 C24 174.63(13) C5 C10 C18 C22 -179.29(13) C5 C10 C21 C27 179.45(14) C6 C7 C11 O1 -23.52(16) C6 C7 C11 N2 160.07(11) C6 C7 C13 C5 128.07(12) C6 C7 C13 C12 -49.45(15) C6 C7 C15 C8 -129.68(11) C6 C7 C15 C20 -12.15(15) C7 C15 C20 C23 177.75(12) C8 C5 C10 C18 -62.26(17) C8 C5 C10 C21 117.19(15) C8 C5 C13 C7 -1.00(14) C8 C5 C13 C12 176.24(12) C8 C15 C20 C23 -66.64(16) C9 C12 C13 C5 156.84(13) C9 C12 C13 C7 -26.16(18) C9 C12 C19 C17 -1.8(2) C10 C5 C8 C15 172.14(11) C10 C5 C8 C25 -10.9(2) C10 C5 C13 C7 -179.19(12) C10 C5 C13 C12 -1.9(2) C10 C18 C22 C28 -0.5(2) C10 C21 C27 C28 0.2(3) C11 C7 C13 C5 -109.67(12) C11 C7 C13 C12 72.80(14) C11 C7 C15 C8 112.36(11) C11 C7 C15 C20 -130.12(11) C12 C9 C16 C14 -0.1(2) C13 C5 C8 C15 -6.21(15) C13 C5 C8 C25 170.71(14) C13 C5 C10 C18 115.78(16) C13 C5 C10 C21 -64.8(2) C13 C7 C11 O1 -147.16(12) C13 C7 C11 N2 36.42(16) C13 C7 C15 C8 -10.26(12) C13 C7 C15 C20 107.27(12) C13 C12 C19 C17 179.06(12) C14 C17 C19 C12 1.2(2) C15 C7 C11 O1 97.43(13) C15 C7 C11 N2 -78.99(13) C15 C7 C13 C5 7.31(13) C15 C7 C13 C12 -170.21(11) C15 C8 C25 C24 -8.8(2) C15 C20 C23 C26 6.5(2) C16 C9 C12 C13 -179.62(13) C16 C9 C12 C19 1.3(2) C16 C14 C17 C19 0.0(2) C17 C14 C16 C9 -0.6(2) C18 C10 C21 C27 -1.1(2) C18 C22 C28 C27 -0.4(3) C19 C12 C13 C5 -24.1(2) C19 C12 C13 C7 152.94(12) C20 C23 C26 C24 34.4(2) C21 C10 C18 C22 1.2(2) C21 C27 C28 C22 0.5(3) C25 C8 C15 C7 -166.87(13) C25 C8 C15 C20 68.50(17) C25 C24 C26 C23 -1.5(2) C26 C24 C25 C8 -30.8(2)