#------------------------------------------------------------------------------ #$Date: 2019-11-17 08:30:10 +0200 (Sun, 17 Nov 2019) $ #$Revision: 228865 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/89/1548989.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_1548989 loop_ _publ_author_name 'Rosenberg, M.' 'Rostgaard, K. R.' 'Liao, Z.' 'Madsen, A \/O' 'Martinez, K. L.' 'Vosch, T.' 'Laursen, B. W.' _publ_section_title ; Design, synthesis, and time-gated cell imaging of carbon-bridged triangulenium dyes with long fluorescence lifetime and red emission. ; _journal_issue 12 _journal_name_full 'Chemical science' _journal_page_first 3122 _journal_page_last 3130 _journal_paper_doi 10.1039/c8sc00089a _journal_volume 9 _journal_year 2018 _chemical_formula_moiety 'F6 P, C21 H15 N2 O' _chemical_formula_sum 'C21 H15 F6 N2 O P' _chemical_formula_weight 456.32 _chemical_name_systematic '4,8-dimethyl-4,8-diaza-12-oxatriangulenium hexafluorophosphate' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_date 2016-05-03 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2017-06-21 deposited with the CCDC. 2018-02-16 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 96.101(14) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.861(3) _cell_length_b 10.695(4) _cell_length_c 23.818(10) _cell_measurement_reflns_used 3743 _cell_measurement_temperature 123 _cell_measurement_theta_max 29.87 _cell_measurement_theta_min 3.44 _cell_volume 1737.8(12) _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 'ShelXL (Sheldrick, 2015)' _computing_structure_solution ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 123 _diffrn_detector 'Bruker Photon 100 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CMOS area detector' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'four-circle kappa-geometry diffractometer' _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_unetI/netI 0.0924 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1546 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 3.44 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_T_max 0.7466 _exptl_absorpt_correction_T_min 0.5720 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/3 (Bruker,2014) was used for absorption correction. wR2(int) was 0.1594 before and 0.0787 after correction. The Ratio of minimum to maximum transmission is 0.7661. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear red' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.744 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 928 _exptl_crystal_recrystallization_method CH3CN/2-propanol _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.466 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.087 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.228 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 1546 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.228 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0695 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2257 _refine_ls_wR_factor_ref 0.2350 _reflns_number_gt 944 _reflns_number_total 1546 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL MO_D8V1234_0MA OLEX2: imported from CIF CELL 0.71073 6.861 10.695 23.818 90 96.101 90 ZERR 4 0.003 0.004 0.01 0 0.014 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H F N O P UNIT 84 60 24 8 4 4 L.S. 16 0 0 PLAN 20 MORE -1 BOND $H CONF fmap 2 53 acta 52 SHEL 100 0.84 OMIT 1 1 3 OMIT -1 1 5 REM REM REM WGHT 0.100000 FVAR 0.06886 P1 6 1.000000 0.500000 0.500000 10.50000 0.02723 0.01338 = 0.01611 0.00207 0.00545 0.00196 F8 3 0.973915 0.506354 0.432015 11.00000 0.04934 0.02362 = 0.01440 0.00047 0.00127 -0.00495 F9 3 0.833664 0.604176 0.501693 11.00000 0.03973 0.02754 = 0.03042 0.00657 0.01027 0.01517 F11 3 0.837523 0.392699 0.498315 11.00000 0.03742 0.03222 = 0.03129 0.00245 0.00316 -0.01074 O13 5 0.500000 0.248765 0.250000 10.50000 0.03307 0.01662 = 0.02101 0.00000 0.00127 0.00000 N3 4 0.529696 0.639552 0.149334 11.00000 0.02076 0.01915 = 0.01875 0.00241 0.00325 -0.00075 C2 1 0.500000 0.643327 0.250000 10.50000 0.02017 0.01004 = 0.02470 0.00000 0.00411 0.00000 C3 1 0.500000 0.511368 0.250000 10.50000 0.00987 0.01451 = 0.01701 0.00000 0.00150 0.00000 C5 1 0.483509 0.444873 0.300458 11.00000 0.01479 0.01485 = 0.02853 0.00141 0.00233 0.00224 C8 1 0.500000 0.899908 0.250000 10.50000 0.01483 0.01567 = 0.03556 0.00000 0.00341 0.00000 AFIX 43 H8 2 0.499999 0.986864 0.250000 10.50000 -1.20000 AFIX 0 C11 1 0.488088 0.312612 0.300427 11.00000 0.01738 0.01488 = 0.02532 -0.00301 0.00147 0.00339 C15 1 0.470088 0.509055 0.351534 11.00000 0.01707 0.02045 = 0.01639 0.00116 0.00326 -0.00133 C1 1 0.515035 0.708333 0.198979 11.00000 0.01615 0.02059 = 0.01306 0.00186 0.00156 -0.00533 C10 1 0.457998 0.310911 0.397231 11.00000 0.02843 0.02612 = 0.02110 0.01159 0.00481 -0.00125 AFIX 43 H10 2 0.447538 0.265738 0.430140 11.00000 -1.20000 AFIX 0 C12 1 0.515645 0.838159 0.199750 11.00000 0.01997 0.02500 = 0.02020 0.00440 0.00072 -0.00171 AFIX 43 H12 2 0.526471 0.883045 0.166783 11.00000 -1.20000 AFIX 0 C0AA 1 0.457934 0.439775 0.400505 11.00000 0.02534 0.02708 = 0.02040 0.00130 0.00278 0.00224 AFIX 43 H0AA 2 0.449899 0.479657 0.434879 11.00000 -1.20000 AFIX 0 C21 1 0.472856 0.244330 0.347379 11.00000 0.02637 0.01405 = 0.03257 0.00537 -0.00014 -0.00308 AFIX 43 H21 2 0.472271 0.157390 0.346613 11.00000 -1.20000 AFIX 0 C26 1 0.536014 0.705480 0.094599 11.00000 0.04541 0.02797 = 0.01575 0.00841 0.00565 0.00509 AFIX 137 H26A 2 0.648320 0.677885 0.077151 11.00000 -1.50000 H26B 2 0.544815 0.793984 0.101101 11.00000 -1.50000 H26C 2 0.418986 0.687138 0.070205 11.00000 -1.50000 HKLF 4 REM MO_D8V1234_0MA OLEX2: imported from CIF REM R1 = 0.0695 for 944 Fo > 4sig(Fo) and 0.1018 for all 1546 data REM 145 parameters refined using 0 restraints END WGHT 0.0126 12.9219 REM Highest difference peak 0.466, deepest hole -0.421, 1-sigma level 0.087 Q1 1 0.5059 0.6190 0.0029 11.00000 0.05 0.47 Q2 1 0.6387 0.4844 0.4997 11.00000 0.05 0.36 Q3 1 0.5903 1.0989 0.2437 11.00000 0.05 0.29 Q4 1 0.4561 0.8733 0.1380 11.00000 0.05 0.26 Q5 1 0.7523 0.4535 0.4023 11.00000 0.05 0.26 Q6 1 0.5420 0.1041 0.3475 11.00000 0.05 0.26 Q7 1 0.6576 0.5086 0.2425 11.00000 0.05 0.24 Q8 1 0.5921 0.7520 0.2030 11.00000 0.05 0.23 Q9 1 0.2868 0.1455 0.3537 11.00000 0.05 0.23 Q10 1 0.6802 0.2536 0.2496 11.00000 0.05 0.23 Q11 1 0.6876 0.3165 0.3060 11.00000 0.05 0.22 Q12 1 0.3504 0.4805 0.4365 11.00000 0.05 0.22 Q13 1 0.4479 0.1799 0.4561 11.00000 0.05 0.22 Q14 1 0.5000 0.3982 0.2500 10.50000 0.05 0.22 Q15 1 1.1065 0.5398 0.3983 11.00000 0.05 0.21 Q16 1 0.8872 0.5008 0.3991 11.00000 0.05 0.20 Q17 1 0.6280 0.2010 0.3961 11.00000 0.05 0.20 Q18 1 0.3245 0.6853 0.2024 11.00000 0.05 0.20 Q19 1 0.3469 0.7864 0.1411 11.00000 0.05 0.20 Q20 1 0.8693 0.3624 0.5490 11.00000 0.05 0.19 REM The information below was added by Olex2. REM REM R1 = 0.0695 for 944 Fo > 4sig(Fo) and 0.1018 for all 2718 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.47, deepest hole -0.42 REM Mean Shift 0, Max Shift -0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1018 REM R1_gt = 0.0695 REM wR_ref = GooF REM GOOF = Restrained REM Shift_max = -0.000 REM Shift_mean = 0 REM Reflections_all = 2718 REM Reflections_gt = 944 REM Parameters = n/a REM Hole = -0.42 REM Peak = 0.47 REM Flack = n/a ; _cod_data_source_file c8sc00089a2.cif _cod_data_source_block mo_d8v1234_0ma _cod_depositor_comments 'Adding full bibliography for 1548989--1548992.cif.' _cod_database_code 1548989 _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: C8(H8), C10(H10), C12(H12), C0AA(H0AA), C21(H21) 2.b Idealised Me refined as rotating group: C26(H26A,H26B,H26C) ; _olex2_exptl_crystal_mounting_method 'on kapton loop' _olex2_submission_original_sample_id D8V1234 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_site_symmetry_order _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy P1 P 1.0000 0.5000 0.5000 0.0187(6) Uani 1 2 d 2 S T P F8 F 0.9739(5) 0.5064(3) 0.43201(12) 0.0293(9) Uani 1 1 d 1 . . . F9 F 0.8337(5) 0.6042(3) 0.50169(13) 0.0321(10) Uani 1 1 d 1 . . . F11 F 0.8375(5) 0.3927(3) 0.49832(14) 0.0337(10) Uani 1 1 d 1 . . . O13 O 0.5000 0.2488(5) 0.2500 0.0237(13) Uani 1 2 d 2 S T P N3 N 0.5297(6) 0.6396(4) 0.14933(18) 0.0195(11) Uani 1 1 d 1 . . . C2 C 0.5000 0.6433(7) 0.2500 0.0182(17) Uani 1 2 d 2 S T P C3 C 0.5000 0.5114(7) 0.2500 0.0138(16) Uani 1 2 d 2 S T P C5 C 0.4835(8) 0.4449(5) 0.3005(2) 0.0194(12) Uani 1 1 d 1 . . . C8 C 0.5000 0.8999(8) 0.2500 0.0220(19) Uani 1 2 d 2 S T P H8 H 0.5000 0.9869 0.2500 0.026 Uiso 1 2 calc 2 RS T P C11 C 0.4881(8) 0.3126(5) 0.3004(2) 0.0193(13) Uani 1 1 d 1 . . . C15 C 0.4701(7) 0.5091(5) 0.3515(2) 0.0179(12) Uani 1 1 d 1 . . . C1 C 0.5150(8) 0.7083(5) 0.1990(2) 0.0166(12) Uani 1 1 d 1 . . . C10 C 0.4580(8) 0.3109(6) 0.3972(2) 0.0251(15) Uani 1 1 d 1 . . . H10 H 0.4475 0.2657 0.4301 0.030 Uiso 1 1 calc 1 R . . C12 C 0.5156(7) 0.8382(5) 0.1997(2) 0.0218(13) Uani 1 1 d 1 . . . H12 H 0.5265 0.8830 0.1668 0.026 Uiso 1 1 calc 1 R . . C0AA C 0.4579(8) 0.4398(6) 0.4005(2) 0.0242(13) Uani 1 1 d 1 . . . H0AA H 0.4499 0.4797 0.4349 0.029 Uiso 1 1 calc 1 R . . C21 C 0.4729(8) 0.2443(6) 0.3474(2) 0.0246(14) Uani 1 1 d 1 . . . H21 H 0.4723 0.1574 0.3466 0.029 Uiso 1 1 calc 1 R . . C26 C 0.5360(9) 0.7055(6) 0.0946(2) 0.0295(16) Uani 1 1 d 1 . . . H26A H 0.6483 0.6779 0.0772 0.044 Uiso 1 1 calc 1 GR . . H26B H 0.5448 0.7940 0.1011 0.044 Uiso 1 1 calc 1 GR . . H26C H 0.4190 0.6871 0.0702 0.044 Uiso 1 1 calc 1 GR . . 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 P1 0.0272(11) 0.0134(10) 0.0161(11) 0.0021(9) 0.0054(8) 0.0020(10) F8 0.049(2) 0.0236(18) 0.0144(17) 0.0005(16) 0.0013(14) -0.0050(18) F9 0.040(2) 0.028(2) 0.030(2) 0.0066(15) 0.0103(16) 0.0152(17) F11 0.037(2) 0.032(2) 0.031(2) 0.0025(16) 0.0032(16) -0.0107(18) O13 0.033(3) 0.017(3) 0.021(3) 0.000 0.001(2) 0.000 N3 0.021(2) 0.019(3) 0.019(3) 0.002(2) 0.0032(19) -0.001(2) C2 0.020(4) 0.010(4) 0.025(4) 0.000 0.004(3) 0.000 C3 0.010(3) 0.015(4) 0.017(4) 0.000 0.002(3) 0.000 C5 0.015(3) 0.015(3) 0.029(3) 0.001(3) 0.002(2) 0.002(2) C8 0.015(4) 0.016(4) 0.036(5) 0.000 0.003(3) 0.000 C11 0.017(3) 0.015(3) 0.025(3) -0.003(3) 0.001(2) 0.003(3) C15 0.017(3) 0.020(3) 0.016(3) 0.001(2) 0.003(2) -0.001(3) C1 0.016(3) 0.021(3) 0.013(3) 0.002(2) 0.002(2) -0.005(3) C10 0.028(3) 0.026(4) 0.021(3) 0.012(3) 0.005(3) -0.001(3) C12 0.020(3) 0.025(3) 0.020(3) 0.004(3) 0.001(2) -0.002(3) C0AA 0.025(3) 0.027(3) 0.020(3) 0.001(3) 0.003(2) 0.002(3) C21 0.026(3) 0.014(3) 0.033(4) 0.005(3) -0.000(3) -0.003(3) C26 0.045(4) 0.028(4) 0.016(3) 0.008(3) 0.006(3) 0.005(3) 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' F F 0.0171 0.0103 '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' P P 0.1023 0.0942 '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 F8 P1 F8 180.00(2) . 5_766 F9 P1 F8 90.42(17) 5_766 . F9 P1 F8 89.58(17) 5_766 5_766 F9 P1 F8 90.42(17) . 5_766 F9 P1 F8 89.58(17) . . F9 P1 F9 180.0(3) 5_766 . F11 P1 F8 90.13(17) 5_766 5_766 F11 P1 F8 89.87(17) 5_766 . F11 P1 F8 89.86(17) . 5_766 F11 P1 F8 90.14(17) . . F11 P1 F9 90.18(18) 5_766 5_766 F11 P1 F9 90.18(18) . . F11 P1 F9 89.82(18) 5_766 . F11 P1 F9 89.82(18) . 5_766 F11 P1 F11 180.0 5_766 . C11 O13 C11 121.2(6) 2_655 . C15 N3 C1 122.4(4) 2_655 . C15 N3 C26 117.5(5) 2_655 . C1 N3 C26 120.1(5) . . C3 C2 C1 119.5(4) . 2_655 C3 C2 C1 119.5(4) . . C1 C2 C1 121.1(7) . 2_655 C2 C3 C5 120.3(4) . . C2 C3 C5 120.3(4) . 2_655 C5 C3 C5 119.5(8) 2_655 . C3 C5 C11 120.0(6) . . C15 C5 C3 120.6(6) . . C15 C5 C11 119.4(5) . . C12 C8 H8 118.6 . . C12 C8 H8 118.6 2_655 . C12 C8 C12 122.9(8) . 2_655 O13 C11 C5 119.6(5) . . C21 C11 O13 117.8(5) . . C21 C11 C5 122.5(5) . . N3 C15 C5 118.3(5) 2_655 . C0AA C15 N3 123.0(5) . 2_655 C0AA C15 C5 118.7(6) . . N3 C1 C2 119.0(5) . . C12 C1 N3 122.3(5) . . C12 C1 C2 118.7(5) . . C0AA C10 H10 118.1 . . C0AA C10 C21 123.9(5) . . C21 C10 H10 118.1 . . C8 C12 C1 119.3(5) . . C8 C12 H12 120.4 . . C1 C12 H12 120.4 . . C15 C0AA H0AA 120.5 . . C10 C0AA C15 118.9(5) . . C10 C0AA H0AA 120.5 . . C11 C21 C10 116.6(6) . . C11 C21 H21 121.7 . . C10 C21 H21 121.7 . . N3 C26 H26A 109.5 . . N3 C26 H26B 109.5 . . N3 C26 H26C 109.5 . . H26A C26 H26B 109.5 . . H26A C26 H26C 109.5 . . H26B C26 H26C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 P1 F8 1.612(3) 5_766 P1 F8 1.612(3) . P1 F9 1.598(3) 5_766 P1 F9 1.598(3) . P1 F11 1.597(3) . P1 F11 1.597(3) 5_766 O13 C11 1.391(6) 2_655 O13 C11 1.392(6) . N3 C15 1.396(7) 2_655 N3 C1 1.405(7) . N3 C26 1.487(7) . C2 C3 1.411(10) . C2 C1 1.413(6) 2_655 C2 C1 1.413(6) . C3 C5 1.411(7) 2_655 C3 C5 1.411(7) . C5 C11 1.415(8) . C5 C15 1.408(8) . C8 H8 0.9300 . C8 C12 1.381(7) . C8 C12 1.381(7) 2_655 C11 C21 1.349(8) . C15 N3 1.396(7) 2_655 C15 C0AA 1.392(8) . C1 C12 1.389(8) . C10 H10 0.9300 . C10 C0AA 1.380(9) . C10 C21 1.397(8) . C12 H12 0.9300 . C0AA H0AA 0.9300 . C21 H21 0.9300 . C26 H26A 0.9600 . C26 H26B 0.9600 . C26 H26C 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_4 O13 C11 C21 C10 -179.0(4) . . N3 C15 C0AA C10 179.8(5) 2_655 . N3 C1 C12 C8 179.8(4) . . C2 C3 C5 C11 -178.6(4) . . C2 C3 C5 C15 -1.0(5) . . C2 C1 C12 C8 -0.5(7) . . C3 C2 C1 N3 -0.0(5) . . C3 C2 C1 C12 -179.7(4) . . C3 C5 C11 O13 -2.9(8) . . C3 C5 C11 C21 -180.0(4) . . C3 C5 C15 N3 1.0(7) . 2_655 C3 C5 C15 C0AA -178.7(4) . . C5 C3 C5 C11 1.4(4) 2_655 . C5 C3 C5 C15 179.0(5) 2_655 . C5 C11 C21 C10 -1.9(8) . . C5 C15 C0AA C10 -0.5(8) . . C11 O13 C11 C5 1.4(4) 2_655 . C11 O13 C11 C21 178.7(6) 2_655 . C11 C5 C15 N3 178.6(5) . 2_655 C11 C5 C15 C0AA -1.2(7) . . C15 N3 C1 C2 0.0(7) 2_655 . C15 N3 C1 C12 179.7(5) 2_655 . C15 C5 C11 O13 179.6(4) . . C15 C5 C11 C21 2.5(9) . . C1 C2 C3 C5 0.5(3) . 2_655 C1 C2 C3 C5 -179.5(3) 2_655 2_655 C1 C2 C3 C5 -179.5(3) . . C1 C2 C3 C5 0.5(3) 2_655 . C1 C2 C1 N3 180.0(5) 2_655 . C1 C2 C1 C12 0.3(4) 2_655 . C12 C8 C12 C1 0.3(4) 2_655 . C0AA C10 C21 C11 0.1(9) . . C21 C10 C0AA C15 1.1(9) . . C26 N3 C1 C2 177.1(4) . . C26 N3 C1 C12 -3.2(7) . .