#------------------------------------------------------------------------------ #$Date: 2017-05-31 07:50:14 +0300 (Wed, 31 May 2017) $ #$Revision: 197067 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/83/7228348.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_7228348 loop_ _publ_author_name 'Sok, Nicolas' 'Baglin, Isabelle' 'Basset, Christelle' 'Fakkor, Fatima' 'Kohli, Evelyne' 'Rousselin, Yoann' 'Bernhard, Claire' 'Boschetti, Fr\'ed\'eric' 'Goze, Christine' 'Denat, Franck' _publ_section_title ; Straightforward synthesis of bis-tetraazacycloalkanes: towards new potential CXCR4 antagonists? ; _journal_issue 45 _journal_name_full 'RSC Adv.' _journal_page_first 28291 _journal_paper_doi 10.1039/C7RA04218C _journal_volume 7 _journal_year 2017 _chemical_formula_moiety 'C28 H52 N10, H2 O ' _chemical_formula_sum 'C28 H54 N10 O' _chemical_formula_weight 546.81 _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' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2016-04-01 _audit_creation_method ; Olex2 1.2 (compiled Feb 16 2016 13:09:46 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2016-04-26 deposited with the CCDC. 2017-05-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.3720(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.4792(3) _cell_length_b 15.0992(4) _cell_length_c 17.6024(4) _cell_measurement_reflns_used 28874 _cell_measurement_temperature 115(2) _cell_measurement_theta_max 27.485 _cell_measurement_theta_min 0.998 _cell_volume 3050.90(13) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _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 'SIR97 (Burla et al., 2007)' _diffrn_ambient_temperature 115(2) _diffrn_detector 'CCD Plate' _diffrn_detector_area_resol_mean 9 _diffrn_detector_type CCD _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f and \w scans'' _diffrn_orient_matrix_type 'Nonius Collect from scalepack cell' _diffrn_radiation_collimation '0.6 mm' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_unetI/netI 0.0525 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 12417 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.502 _diffrn_reflns_theta_min 1.777 _diffrn_source 'X-ray tube' _diffrn_source_target Mo _diffrn_source_type 'Siemens KFF Mo 2K-180' _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 1200 _exptl_crystal_recrystallization_method 'The material was recrystallised from diethyl ether by slow evaporation' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.726 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 355 _refine_ls_number_reflns 6959 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.1043 _refine_ls_R_factor_gt 0.0713 _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^)+(0.0923P)^2^+2.7095P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1799 _refine_ls_wR_factor_ref 0.1991 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4919 _reflns_number_total 6959 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 07ns343.res created by SHELXL-2014/7 TITL 07ns343 in P 21/n CELL 0.71073 11.4792 15.0992 17.6024 90 90.372 90 ZERR 4 0.0003 0.0004 0.0004 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 112 216 40 4 EQIV $1 -1+X,+Y,+Z L.S. 10 PLAN -10 SIZE 0.2 0.32 0.27 TEMP -158 HTAB O1 N2_$1 HTAB O1 N7 HTAB N2 N3 HTAB N7 N8 BOND $H HTAB MORE -1 CONF fmap 2 acta MERG 2 OMIT 1 0 1 OMIT 0 0 2 OMIT 1 1 1 OMIT -1 0 1 OMIT 1 1 0 OMIT -1 1 1 OMIT 0 1 2 OMIT -2 2 2 OMIT -4 3 8 OMIT 3 0 9 OMIT 3 5 7 OMIT 4 1 2 OMIT -3 4 3 OMIT -4 4 2 OMIT -5 5 1 OMIT -4 6 1 OMIT 3 2 6 OMIT 2 6 4 OMIT 1 8 4 REM REM REM WGHT 0.092300 2.709500 FVAR 0.51672 AFIX 6 O1 4 0.108540 0.242592 0.413703 11.00000 0.02648 0.07399 = 0.02838 0.00916 0.00163 0.00526 H1C 2 0.050593 0.263439 0.387177 11.00000 -1.50000 H1D 2 0.161369 0.221934 0.383379 11.00000 -1.50000 AFIX 0 N1 3 0.808289 0.153134 0.300174 11.00000 0.02873 0.03324 = 0.02877 -0.00188 0.00280 0.00563 N2 3 0.925460 0.318656 0.328550 11.00000 0.03089 0.03101 = 0.03618 0.00023 -0.00388 0.00180 N10 3 0.564548 0.455784 0.321441 11.00000 0.02989 0.02471 = 0.03020 -0.00223 0.00371 -0.00361 AFIX 3 0.8700 H2 2 0.861437 0.302344 0.351361 11.00000 -1.20000 AFIX 0 N3 3 0.768938 0.359540 0.461094 11.00000 0.03131 0.05784 = 0.03902 -0.01273 -0.00468 0.01214 AFIX 3 0.8700 H3 2 0.698858 0.361480 0.479564 11.00000 -1.20000 AFIX 0 N4 3 0.744715 0.163956 0.460551 11.00000 0.02820 0.05381 = 0.03235 0.01058 0.00179 0.00370 AFIX 3 0.8700 H4 2 0.728565 0.199536 0.423061 11.00000 -1.20000 AFIX 0 N5 3 0.631506 0.077339 0.295878 11.00000 0.03381 0.02860 = 0.03725 -0.00219 0.00297 0.00461 AFIX 3 0.8700 H5 2 0.595086 0.116559 0.323038 11.00000 -1.20000 AFIX 0 N6 3 0.395403 0.370215 0.312868 11.00000 0.02272 0.02611 = 0.02541 0.00135 0.00491 0.00054 N7 3 0.293834 0.192916 0.317569 11.00000 0.02967 0.02942 = 0.02595 -0.00112 -0.00368 -0.00511 AFIX 3 0.8700 H7 2 0.356014 0.202626 0.344839 11.00000 -1.20000 AFIX 0 N8 3 0.449374 0.131497 0.443699 11.00000 0.02660 0.03390 = 0.03347 0.00483 0.00114 0.00246 AFIX 3 0.8700 H8 2 0.521664 0.127717 0.458489 11.00000 -1.20000 AFIX 0 N9 3 0.465696 0.326226 0.468112 11.00000 0.02557 0.03620 = 0.02561 -0.00528 0.00509 -0.00118 AFIX 3 0.8700 H9 2 0.479696 0.299466 0.425362 11.00000 -1.20000 AFIX 3 0.8700 H10 2 0.607517 0.414786 0.342592 11.00000 -1.20000 AFIX 0 C1 1 0.913942 0.179707 0.260280 11.00000 0.02734 0.04377 = 0.03104 -0.00689 0.00470 0.00364 AFIX 23 H1A 2 0.914153 0.152570 0.209082 11.00000 -1.20000 H1B 2 0.982963 0.157506 0.288405 11.00000 -1.20000 AFIX 0 C2 1 0.922113 0.279069 0.252724 11.00000 0.02805 0.04548 = 0.02734 0.00640 0.00545 0.00224 AFIX 23 H2A 2 0.993438 0.295133 0.224568 11.00000 -1.20000 H2B 2 0.853912 0.301771 0.224047 11.00000 -1.20000 AFIX 0 C3 1 0.927166 0.415110 0.328680 11.00000 0.04457 0.03125 = 0.04739 0.00226 -0.00300 0.00272 AFIX 23 H3A 2 0.856261 0.437579 0.302812 11.00000 -1.20000 H3B 2 0.995669 0.436160 0.299962 11.00000 -1.20000 AFIX 0 C4 1 0.932423 0.451457 0.408251 11.00000 0.03764 0.03153 = 0.05744 -0.00337 -0.00784 0.00257 AFIX 23 H4A 2 0.959920 0.513525 0.405726 11.00000 -1.20000 H4B 2 0.991317 0.417319 0.437321 11.00000 -1.20000 AFIX 0 C5 1 0.819431 0.449712 0.451798 11.00000 0.04417 0.04089 = 0.04671 -0.01674 -0.00819 0.01082 AFIX 23 H5A 2 0.833083 0.475627 0.502746 11.00000 -1.20000 H5B 2 0.761893 0.487579 0.425093 11.00000 -1.20000 AFIX 0 C6 1 0.835213 0.305218 0.513708 11.00000 0.04222 0.05225 = 0.03769 -0.00907 -0.00633 0.00823 AFIX 23 H6A 2 0.847207 0.338072 0.561799 11.00000 -1.20000 H6B 2 0.912680 0.292370 0.491908 11.00000 -1.20000 AFIX 0 C7 1 0.773439 0.219918 0.529814 11.00000 0.02773 0.07721 = 0.02480 0.00485 0.00171 0.00138 AFIX 23 H7A 2 0.699984 0.233575 0.556547 11.00000 -1.20000 H7B 2 0.822486 0.184308 0.564765 11.00000 -1.20000 AFIX 0 C8 1 0.843265 0.112997 0.435034 11.00000 0.03896 0.04295 = 0.04021 0.00955 0.00264 0.00581 AFIX 23 H8A 2 0.856620 0.062709 0.470113 11.00000 -1.20000 H8B 2 0.913855 0.150665 0.435680 11.00000 -1.20000 AFIX 0 C9 1 0.822742 0.078413 0.355994 11.00000 0.03933 0.02775 = 0.04511 0.00392 0.00233 0.01162 AFIX 13 H9A 2 0.890235 0.040750 0.340581 11.00000 -1.20000 AFIX 0 C10 1 0.707771 0.024805 0.346090 11.00000 0.04358 0.02528 = 0.04496 0.00313 -0.00120 0.00112 AFIX 23 H10A 2 0.723986 -0.033718 0.323107 11.00000 -1.20000 H10B 2 0.670238 0.015463 0.395929 11.00000 -1.20000 AFIX 0 C11 1 0.712181 0.126823 0.248534 11.00000 0.02820 0.03052 = 0.02997 -0.00698 0.00166 0.00470 AFIX 13 H11 2 0.743874 0.086203 0.208841 11.00000 -1.20000 AFIX 0 C12 1 0.655471 0.205114 0.209636 11.00000 0.02051 0.03148 = 0.02529 -0.00491 0.00237 -0.00323 C13 1 0.650775 0.212349 0.130771 11.00000 0.02523 0.03733 = 0.02661 -0.00978 0.00736 -0.00717 AFIX 43 H13 2 0.683841 0.166920 0.100428 11.00000 -1.20000 AFIX 0 C14 1 0.598985 0.284280 0.095891 11.00000 0.02827 0.04145 = 0.01936 -0.00191 0.00139 -0.01311 AFIX 43 H14 2 0.597942 0.288627 0.042050 11.00000 -1.20000 AFIX 0 C15 1 0.548356 0.350348 0.139657 11.00000 0.02524 0.03223 = 0.02332 0.00344 -0.00066 -0.00760 AFIX 43 H15 2 0.512930 0.399939 0.115643 11.00000 -1.20000 AFIX 0 C16 1 0.549400 0.344064 0.218818 11.00000 0.02123 0.02782 = 0.02169 0.00072 0.00164 -0.00556 C17 1 0.604129 0.271867 0.252674 11.00000 0.02311 0.03093 = 0.02036 -0.00238 0.00238 0.00048 AFIX 43 H17 2 0.606593 0.267933 0.306525 11.00000 -1.20000 AFIX 0 C18 1 0.487829 0.411542 0.267188 11.00000 0.02328 0.02362 = 0.02670 0.00460 0.00359 0.00022 AFIX 13 H18 2 0.451820 0.457180 0.233221 11.00000 -1.20000 AFIX 0 C19 1 0.484437 0.491018 0.379072 11.00000 0.04694 0.02423 = 0.03836 -0.00568 0.01375 -0.00655 AFIX 23 H19A 2 0.462202 0.552690 0.366553 11.00000 -1.20000 H19B 2 0.522113 0.490514 0.429822 11.00000 -1.20000 AFIX 0 C20 1 0.375523 0.430412 0.378646 11.00000 0.03588 0.02502 = 0.03622 -0.00035 0.01238 0.00446 AFIX 13 H20 2 0.304157 0.466868 0.369201 11.00000 -1.20000 AFIX 0 C21 1 0.360586 0.376721 0.451137 11.00000 0.02970 0.02871 = 0.03132 -0.00483 0.00588 0.00021 AFIX 23 H21A 2 0.343519 0.417106 0.493952 11.00000 -1.20000 H21B 2 0.293867 0.335723 0.445082 11.00000 -1.20000 AFIX 0 C22 1 0.445976 0.259198 0.528521 11.00000 0.02758 0.04779 = 0.02237 0.00097 -0.00016 0.00146 AFIX 23 H22A 2 0.400070 0.287207 0.569433 11.00000 -1.20000 H22B 2 0.522490 0.242556 0.550519 11.00000 -1.20000 AFIX 0 C23 1 0.384317 0.175809 0.504055 11.00000 0.03226 0.03727 = 0.02837 0.00805 0.00514 0.00081 AFIX 23 H23A 2 0.376620 0.135453 0.548065 11.00000 -1.20000 H23B 2 0.305091 0.190594 0.485470 11.00000 -1.20000 AFIX 0 C24 1 0.401499 0.043635 0.424041 11.00000 0.04334 0.02879 = 0.04380 0.00421 0.00172 0.00092 AFIX 23 H24A 2 0.389832 0.009487 0.471397 11.00000 -1.20000 H24B 2 0.459151 0.011358 0.392930 11.00000 -1.20000 AFIX 0 C25 1 0.286528 0.047790 0.380594 11.00000 0.04697 0.02728 = 0.04866 0.00055 -0.00185 -0.01053 AFIX 23 H25A 2 0.227944 0.077085 0.413090 11.00000 -1.20000 H25B 2 0.259364 -0.013454 0.371020 11.00000 -1.20000 AFIX 0 C26 1 0.291627 0.096753 0.304940 11.00000 0.04246 0.03263 = 0.03914 -0.00742 -0.00553 -0.00911 AFIX 23 H26A 2 0.362339 0.078608 0.277052 11.00000 -1.20000 H26B 2 0.222790 0.080971 0.273587 11.00000 -1.20000 AFIX 0 C27 1 0.292106 0.245569 0.248347 11.00000 0.02521 0.04166 = 0.02352 0.00383 -0.00119 -0.00566 AFIX 23 H27A 2 0.221708 0.231344 0.217937 11.00000 -1.20000 H27B 2 0.361530 0.231947 0.217383 11.00000 -1.20000 AFIX 0 C28 1 0.291788 0.343914 0.269919 11.00000 0.02285 0.04022 = 0.03521 0.01336 -0.00077 0.00035 AFIX 23 H28A 2 0.286698 0.379931 0.223018 11.00000 -1.20000 H28B 2 0.221801 0.356587 0.300639 11.00000 -1.20000 AFIX 0 HKLF 4 REM 07ns343 in P 21/n REM R1 = 0.0713 for 4919 Fo > 4sig(Fo) and 0.1043 for all 6959 data REM 355 parameters refined using 0 restraints END WGHT 0.0923 2.7098 REM Instructions for potential hydrogen bonds HTAB O1 N2_$1 HTAB O1 N7 HTAB N2 N3 HTAB N4 N1 HTAB N4 N3 HTAB N7 N8 HTAB N8 N4 HTAB N9 N6 HTAB C21 O1 REM Highest difference peak 0.726, deepest hole -0.326, 1-sigma level 0.061 Q1 1 0.8343 0.1660 0.5028 11.00000 0.05 0.73 Q2 1 0.8942 0.1298 0.3321 11.00000 0.05 0.55 Q3 1 0.7533 0.3021 0.5015 11.00000 0.05 0.53 Q4 1 0.4129 0.4365 0.4230 11.00000 0.05 0.50 Q5 1 0.8602 0.3708 0.3452 11.00000 0.05 0.50 Q6 1 0.8297 0.2081 0.2833 11.00000 0.05 0.50 Q7 1 0.3813 0.3144 0.5022 11.00000 0.05 0.48 Q8 1 0.7556 0.1231 0.4334 11.00000 0.05 0.45 Q9 1 0.7835 0.0673 0.4060 11.00000 0.05 0.42 Q10 1 0.8370 0.3941 0.5121 11.00000 0.05 0.41 REM The information below was added by Olex2. REM REM R1 = 0.0713 for 4919 Fo > 4sig(Fo) and 0.1043 for all 12727 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.73, deepest hole -0.33 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1043 REM R1_gt = 0.0713 REM wR_ref = 0.1991 REM GOOF = 1.028 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 12727 REM Reflections_gt = 4919 REM Parameters = n/a REM Hole = -0.33 REM Peak = 0.73 REM Flack = n/a ; _cod_data_source_file c7ra04218c2.cif _cod_data_source_block Compound_3 _cod_database_code 7228348 _publcif_datablock.id {64343868-cd66-4bf2-8930-ef488cc57d34} _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 0.985 _shelx_estimated_absorpt_t_min 0.976 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups At 1.5 times of: All O(H,H) groups 2.a Riding coordinates: N10(H2), N3(H3), N4(H4), N5(H5), N7(H7), N8(H8), N9(H9), N9(H10) 2.b Free rotating group: O1(H1C,H1D) 2.c Ternary CH refined with riding coordinates: C9(H9A), C11(H11), C18(H18), C20(H20) 2.d Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B) 2.e Aromatic/amide H refined with riding coordinates: C13(H13), C14(H14), C15(H15), C17(H17) ; _shelx_shelxl_version_number 2014/7 _olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems' _olex2_exptl_crystal_mounting_method 'The crystal was mounted on a glass fibre with grease' _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 O1 O 0.10854(16) 0.24259(15) 0.41370(10) 0.0429(5) Uani 1 1 d . H1C H 0.0506 0.2634 0.3872 0.064 Uiso 1 1 d G H1D H 0.1614 0.2219 0.3834 0.064 Uiso 1 1 d G N1 N 0.80829(18) 0.15313(13) 0.30017(11) 0.0302(5) Uani 1 1 d . N2 N 0.92546(18) 0.31866(14) 0.32855(12) 0.0327(5) Uani 1 1 d . N10 N 0.56455(17) 0.45578(12) 0.32144(11) 0.0283(4) Uani 1 1 d . H2 H 0.8614 0.3023 0.3514 0.034 Uiso 1 1 d R N3 N 0.7689(2) 0.35954(16) 0.46109(13) 0.0427(6) Uani 1 1 d . H3 H 0.6989 0.3615 0.4796 0.051 Uiso 1 1 d R N4 N 0.74472(18) 0.16396(16) 0.46055(12) 0.0381(5) Uani 1 1 d . H4 H 0.7286 0.1995 0.4231 0.046 Uiso 1 1 d R N5 N 0.63151(18) 0.07734(13) 0.29588(12) 0.0332(5) Uani 1 1 d . H5 H 0.5951 0.1166 0.3230 0.040 Uiso 1 1 d R N6 N 0.39540(16) 0.37021(12) 0.31287(10) 0.0247(4) Uani 1 1 d . N7 N 0.29383(18) 0.19292(13) 0.31757(10) 0.0284(4) Uani 1 1 d . H7 H 0.3560 0.2026 0.3448 0.034 Uiso 1 1 d R N8 N 0.44937(18) 0.13150(13) 0.44370(11) 0.0313(5) Uani 1 1 d . H8 H 0.5217 0.1277 0.4585 0.038 Uiso 1 1 d R N9 N 0.46570(17) 0.32623(14) 0.46811(11) 0.0291(4) Uani 1 1 d . H9 H 0.4797 0.2995 0.4254 0.035 Uiso 1 1 d R H10 H 0.6075 0.4148 0.3426 0.035 Uiso 1 1 d R C1 C 0.9139(2) 0.17971(18) 0.26028(14) 0.0340(6) Uani 1 1 d . H1A H 0.9142 0.1526 0.2091 0.041 Uiso 1 1 calc R H1B H 0.9830 0.1575 0.2884 0.041 Uiso 1 1 calc R C2 C 0.9221(2) 0.27907(17) 0.25272(13) 0.0336(6) Uani 1 1 d . H2A H 0.9934 0.2951 0.2246 0.040 Uiso 1 1 calc R H2B H 0.8539 0.3018 0.2240 0.040 Uiso 1 1 calc R C3 C 0.9272(3) 0.41511(17) 0.32868(16) 0.0411(6) Uani 1 1 d . H3A H 0.8563 0.4376 0.3028 0.049 Uiso 1 1 calc R H3B H 0.9957 0.4362 0.3000 0.049 Uiso 1 1 calc R C4 C 0.9324(2) 0.45146(18) 0.40825(17) 0.0422(6) Uani 1 1 d . H4A H 0.9599 0.5135 0.4057 0.051 Uiso 1 1 calc R H4B H 0.9913 0.4173 0.4373 0.051 Uiso 1 1 calc R C5 C 0.8194(3) 0.44971(19) 0.45180(16) 0.0440(7) Uani 1 1 d . H5A H 0.8331 0.4756 0.5027 0.053 Uiso 1 1 calc R H5B H 0.7619 0.4876 0.4251 0.053 Uiso 1 1 calc R C6 C 0.8352(3) 0.3052(2) 0.51371(16) 0.0441(7) Uani 1 1 d . H6A H 0.8472 0.3381 0.5618 0.053 Uiso 1 1 calc R H6B H 0.9127 0.2924 0.4919 0.053 Uiso 1 1 calc R C7 C 0.7734(2) 0.2199(2) 0.52981(14) 0.0432(7) Uani 1 1 d . H7A H 0.7000 0.2336 0.5565 0.052 Uiso 1 1 calc R H7B H 0.8225 0.1843 0.5648 0.052 Uiso 1 1 calc R C8 C 0.8433(3) 0.11300(19) 0.43503(15) 0.0407(6) Uani 1 1 d . H8A H 0.8566 0.0627 0.4701 0.049 Uiso 1 1 calc R H8B H 0.9139 0.1507 0.4357 0.049 Uiso 1 1 calc R C9 C 0.8227(2) 0.07841(17) 0.35599(15) 0.0374(6) Uani 1 1 d . H9A H 0.8902 0.0407 0.3406 0.045 Uiso 1 1 calc R C10 C 0.7078(2) 0.02480(16) 0.34609(16) 0.0379(6) Uani 1 1 d . H10A H 0.7240 -0.0337 0.3231 0.046 Uiso 1 1 calc R H10B H 0.6702 0.0155 0.3959 0.046 Uiso 1 1 calc R C11 C 0.7122(2) 0.12682(16) 0.24853(13) 0.0296(5) Uani 1 1 d . H11 H 0.7439 0.0862 0.2088 0.035 Uiso 1 1 calc R C12 C 0.65547(19) 0.20511(16) 0.20964(12) 0.0258(5) Uani 1 1 d . C13 C 0.6508(2) 0.21235(17) 0.13077(13) 0.0297(5) Uani 1 1 d . H13 H 0.6838 0.1669 0.1004 0.036 Uiso 1 1 calc R C14 C 0.5990(2) 0.28428(17) 0.09589(12) 0.0297(5) Uani 1 1 d . H14 H 0.5979 0.2886 0.0421 0.036 Uiso 1 1 calc R C15 C 0.5484(2) 0.35035(16) 0.13966(12) 0.0269(5) Uani 1 1 d . H15 H 0.5129 0.3999 0.1156 0.032 Uiso 1 1 calc R C16 C 0.54940(19) 0.34406(15) 0.21882(12) 0.0236(5) Uani 1 1 d . C17 C 0.60413(19) 0.27187(15) 0.25267(12) 0.0248(5) Uani 1 1 d . H17 H 0.6066 0.2679 0.3065 0.030 Uiso 1 1 calc R C18 C 0.48783(19) 0.41154(15) 0.26719(12) 0.0245(5) Uani 1 1 d . H18 H 0.4518 0.4572 0.2332 0.029 Uiso 1 1 calc R C19 C 0.4844(2) 0.49102(16) 0.37907(15) 0.0365(6) Uani 1 1 d . H19A H 0.4622 0.5527 0.3666 0.044 Uiso 1 1 calc R H19B H 0.5221 0.4905 0.4298 0.044 Uiso 1 1 calc R C20 C 0.3755(2) 0.43041(16) 0.37865(14) 0.0323(5) Uani 1 1 d . H20 H 0.3042 0.4669 0.3692 0.039 Uiso 1 1 calc R C21 C 0.3606(2) 0.37672(16) 0.45114(13) 0.0299(5) Uani 1 1 d . H21A H 0.3435 0.4171 0.4940 0.036 Uiso 1 1 calc R H21B H 0.2939 0.3357 0.4451 0.036 Uiso 1 1 calc R C22 C 0.4460(2) 0.25920(17) 0.52852(13) 0.0326(6) Uani 1 1 d . H22A H 0.4001 0.2872 0.5694 0.039 Uiso 1 1 calc R H22B H 0.5225 0.2426 0.5505 0.039 Uiso 1 1 calc R C23 C 0.3843(2) 0.17581(17) 0.50406(13) 0.0326(5) Uani 1 1 d . H23A H 0.3766 0.1355 0.5481 0.039 Uiso 1 1 calc R H23B H 0.3051 0.1906 0.4855 0.039 Uiso 1 1 calc R C24 C 0.4015(2) 0.04363(17) 0.42404(16) 0.0386(6) Uani 1 1 d . H24A H 0.3898 0.0095 0.4714 0.046 Uiso 1 1 calc R H24B H 0.4592 0.0114 0.3929 0.046 Uiso 1 1 calc R C25 C 0.2865(3) 0.04779(17) 0.38059(16) 0.0410(6) Uani 1 1 d . H25A H 0.2279 0.0771 0.4131 0.049 Uiso 1 1 calc R H25B H 0.2594 -0.0135 0.3710 0.049 Uiso 1 1 calc R C26 C 0.2916(3) 0.09675(17) 0.30494(15) 0.0381(6) Uani 1 1 d . H26A H 0.3623 0.0786 0.2771 0.046 Uiso 1 1 calc R H26B H 0.2228 0.0810 0.2736 0.046 Uiso 1 1 calc R C27 C 0.2921(2) 0.24557(16) 0.24835(13) 0.0301(5) Uani 1 1 d . H27A H 0.2217 0.2313 0.2179 0.036 Uiso 1 1 calc R H27B H 0.3615 0.2319 0.2174 0.036 Uiso 1 1 calc R C28 C 0.2918(2) 0.34391(17) 0.26992(14) 0.0328(5) Uani 1 1 d . H28A H 0.2867 0.3799 0.2230 0.039 Uiso 1 1 calc R H28B H 0.2218 0.3566 0.3006 0.039 Uiso 1 1 calc R 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 0.0265(10) 0.0740(14) 0.0284(9) 0.0092(9) 0.0016(7) 0.0053(9) N1 0.0287(11) 0.0332(11) 0.0288(10) -0.0019(8) 0.0028(8) 0.0056(9) N2 0.0309(11) 0.0310(11) 0.0362(11) 0.0002(9) -0.0039(9) 0.0018(9) N10 0.0299(11) 0.0247(10) 0.0302(10) -0.0022(8) 0.0037(8) -0.0036(8) N3 0.0313(12) 0.0578(15) 0.0390(12) -0.0127(11) -0.0047(9) 0.0121(11) N4 0.0282(12) 0.0538(14) 0.0323(11) 0.0106(10) 0.0018(9) 0.0037(10) N5 0.0338(12) 0.0286(10) 0.0372(11) -0.0022(9) 0.0030(9) 0.0046(9) N6 0.0227(10) 0.0261(9) 0.0254(9) 0.0013(8) 0.0049(7) 0.0005(8) N7 0.0297(11) 0.0294(10) 0.0259(9) -0.0011(8) -0.0037(8) -0.0051(8) N8 0.0266(11) 0.0339(11) 0.0335(10) 0.0048(9) 0.0011(8) 0.0025(8) N9 0.0256(11) 0.0362(11) 0.0256(9) -0.0053(8) 0.0051(8) -0.0012(8) C1 0.0273(13) 0.0438(14) 0.0310(12) -0.0069(11) 0.0047(10) 0.0036(11) C2 0.0281(13) 0.0455(15) 0.0273(12) 0.0064(11) 0.0055(9) 0.0022(11) C3 0.0446(16) 0.0313(13) 0.0474(15) 0.0023(12) -0.0030(12) 0.0027(12) C4 0.0376(15) 0.0315(13) 0.0574(17) -0.0034(12) -0.0078(13) 0.0026(11) C5 0.0442(17) 0.0409(15) 0.0467(15) -0.0167(13) -0.0082(13) 0.0108(13) C6 0.0422(17) 0.0523(17) 0.0377(14) -0.0091(13) -0.0063(12) 0.0082(13) C7 0.0277(14) 0.077(2) 0.0248(12) 0.0049(13) 0.0017(10) 0.0014(13) C8 0.0390(15) 0.0429(15) 0.0402(14) 0.0096(12) 0.0026(11) 0.0058(12) C9 0.0393(15) 0.0278(13) 0.0451(14) 0.0039(11) 0.0023(12) 0.0116(11) C10 0.0436(16) 0.0253(12) 0.0450(15) 0.0031(11) -0.0012(12) 0.0011(11) C11 0.0282(12) 0.0305(12) 0.0300(11) -0.0070(10) 0.0017(9) 0.0047(10) C12 0.0205(11) 0.0315(12) 0.0253(11) -0.0049(9) 0.0024(8) -0.0032(9) C13 0.0252(12) 0.0373(13) 0.0266(11) -0.0098(10) 0.0074(9) -0.0072(10) C14 0.0283(12) 0.0415(14) 0.0194(10) -0.0019(10) 0.0014(9) -0.0131(10) C15 0.0252(12) 0.0322(12) 0.0233(10) 0.0034(9) -0.0007(9) -0.0076(10) C16 0.0212(11) 0.0278(11) 0.0217(10) 0.0007(9) 0.0016(8) -0.0056(9) C17 0.0231(11) 0.0309(12) 0.0204(10) -0.0024(9) 0.0024(8) 0.0005(9) C18 0.0233(11) 0.0236(11) 0.0267(11) 0.0046(9) 0.0036(9) 0.0002(9) C19 0.0469(16) 0.0242(12) 0.0384(13) -0.0057(10) 0.0138(12) -0.0066(11) C20 0.0359(14) 0.0250(11) 0.0362(13) -0.0003(10) 0.0124(10) 0.0045(10) C21 0.0297(13) 0.0287(12) 0.0313(12) -0.0048(10) 0.0059(10) 0.0002(10) C22 0.0276(13) 0.0478(15) 0.0224(11) 0.0010(10) -0.0002(9) 0.0015(11) C23 0.0323(13) 0.0373(13) 0.0284(12) 0.0080(10) 0.0051(10) 0.0008(11) C24 0.0433(16) 0.0288(13) 0.0438(15) 0.0042(11) 0.0017(12) 0.0009(11) C25 0.0470(17) 0.0273(13) 0.0487(15) 0.0005(11) -0.0019(13) -0.0105(12) C26 0.0425(16) 0.0326(13) 0.0391(14) -0.0074(11) -0.0055(11) -0.0091(11) C27 0.0252(12) 0.0417(14) 0.0235(11) 0.0038(10) -0.0012(9) -0.0057(10) C28 0.0229(12) 0.0402(14) 0.0352(12) 0.0134(11) -0.0008(10) 0.0003(10) 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 H1C O1 H1D 109.6 C1 N1 C9 115.5(2) C1 N1 C11 113.35(19) C11 N1 C9 106.17(19) C2 N2 H2 106.6 C3 N2 H2 107.0 C3 N2 C2 114.2(2) C18 N10 H10 107.0 C18 N10 C19 103.86(18) C19 N10 H10 108.4 C5 N3 H3 111.8 C6 N3 H3 105.3 C6 N3 C5 112.6(2) C7 N4 H4 108.0 C8 N4 H4 104.9 C8 N4 C7 112.4(2) C10 N5 H5 108.8 C11 N5 H5 106.0 C11 N5 C10 104.01(19) C18 N6 C20 106.26(17) C28 N6 C18 114.80(17) C28 N6 C20 116.08(19) C26 N7 H7 105.3 C27 N7 H7 112.1 C27 N7 C26 114.41(19) C23 N8 H8 107.6 C23 N8 C24 112.9(2) C24 N8 H8 111.4 C21 N9 H9 102.9 C21 N9 C22 111.92(18) C22 N9 H9 109.4 N1 C1 H1A 109.3 N1 C1 H1B 109.3 N1 C1 C2 111.6(2) H1A C1 H1B 108.0 C2 C1 H1A 109.3 C2 C1 H1B 109.3 N2 C2 C1 109.09(19) N2 C2 H2A 109.9 N2 C2 H2B 109.9 C1 C2 H2A 109.9 C1 C2 H2B 109.9 H2A C2 H2B 108.3 N2 C3 H3A 109.3 N2 C3 H3B 109.3 N2 C3 C4 111.5(2) H3A C3 H3B 108.0 C4 C3 H3A 109.3 C4 C3 H3B 109.3 C3 C4 H4A 108.3 C3 C4 H4B 108.3 C3 C4 C5 115.9(2) H4A C4 H4B 107.4 C5 C4 H4A 108.3 C5 C4 H4B 108.3 N3 C5 C4 114.1(2) N3 C5 H5A 108.7 N3 C5 H5B 108.7 C4 C5 H5A 108.7 C4 C5 H5B 108.7 H5A C5 H5B 107.6 N3 C6 H6A 109.4 N3 C6 H6B 109.4 N3 C6 C7 111.1(2) H6A C6 H6B 108.0 C7 C6 H6A 109.4 C7 C6 H6B 109.4 N4 C7 H7A 108.5 N4 C7 H7B 108.5 C6 C7 N4 115.3(2) C6 C7 H7A 108.5 C6 C7 H7B 108.5 H7A C7 H7B 107.5 N4 C8 H8A 109.5 N4 C8 H8B 109.5 N4 C8 C9 110.8(2) H8A C8 H8B 108.1 C9 C8 H8A 109.5 C9 C8 H8B 109.5 N1 C9 H9A 109.4 N1 C9 C10 103.1(2) C8 C9 N1 111.1(2) C8 C9 H9A 109.4 C8 C9 C10 114.3(2) C10 C9 H9A 109.4 N5 C10 C9 106.7(2) N5 C10 H10A 110.4 N5 C10 H10B 110.4 C9 C10 H10A 110.4 C9 C10 H10B 110.4 H10A C10 H10B 108.6 N1 C11 H11 108.7 N1 C11 C12 112.68(19) N5 C11 N1 105.11(19) N5 C11 H11 108.7 N5 C11 C12 112.76(19) C12 C11 H11 108.7 C13 C12 C11 121.8(2) C13 C12 C17 118.1(2) C17 C12 C11 120.1(2) C12 C13 H13 119.4 C14 C13 C12 121.2(2) C14 C13 H13 119.4 C13 C14 H14 120.0 C13 C14 C15 119.9(2) C15 C14 H14 120.0 C14 C15 H15 119.9 C14 C15 C16 120.2(2) C16 C15 H15 119.9 C15 C16 C18 121.1(2) C17 C16 C15 118.8(2) C17 C16 C18 120.02(18) C12 C17 H17 119.2 C16 C17 C12 121.7(2) C16 C17 H17 119.2 N10 C18 N6 105.71(17) N10 C18 C16 113.37(18) N10 C18 H18 108.8 N6 C18 C16 111.34(18) N6 C18 H18 108.8 C16 C18 H18 108.8 N10 C19 H19A 110.3 N10 C19 H19B 110.3 N10 C19 C20 106.90(19) H19A C19 H19B 108.6 C20 C19 H19A 110.3 C20 C19 H19B 110.3 N6 C20 C19 103.67(18) N6 C20 H20 109.6 N6 C20 C21 110.18(18) C19 C20 H20 109.6 C21 C20 C19 113.9(2) C21 C20 H20 109.6 N9 C21 C20 110.67(19) N9 C21 H21A 109.5 N9 C21 H21B 109.5 C20 C21 H21A 109.5 C20 C21 H21B 109.5 H21A C21 H21B 108.1 N9 C22 H22A 108.3 N9 C22 H22B 108.3 N9 C22 C23 115.99(19) H22A C22 H22B 107.4 C23 C22 H22A 108.3 C23 C22 H22B 108.3 N8 C23 C22 110.4(2) N8 C23 H23A 109.6 N8 C23 H23B 109.6 C22 C23 H23A 109.6 C22 C23 H23B 109.6 H23A C23 H23B 108.1 N8 C24 H24A 108.8 N8 C24 H24B 108.8 N8 C24 C25 113.6(2) H24A C24 H24B 107.7 C25 C24 H24A 108.8 C25 C24 H24B 108.8 C24 C25 H25A 108.5 C24 C25 H25B 108.5 C24 C25 C26 114.9(2) H25A C25 H25B 107.5 C26 C25 H25A 108.5 C26 C25 H25B 108.5 N7 C26 C25 110.4(2) N7 C26 H26A 109.6 N7 C26 H26B 109.6 C25 C26 H26A 109.6 C25 C26 H26B 109.6 H26A C26 H26B 108.1 N7 C27 H27A 109.9 N7 C27 H27B 109.9 N7 C27 C28 108.78(19) H27A C27 H27B 108.3 C28 C27 H27A 109.9 C28 C27 H27B 109.9 N6 C28 C27 112.9(2) N6 C28 H28A 109.0 N6 C28 H28B 109.0 C27 C28 H28A 109.0 C27 C28 H28B 109.0 H28A C28 H28B 107.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 H1C 0.8692 O1 H1D 0.8684 N1 C1 1.462(3) N1 C9 1.505(3) N1 C11 1.479(3) N2 H2 0.8751 N2 C2 1.463(3) N2 C3 1.457(3) N10 H10 0.8733 N10 C18 1.457(3) N10 C19 1.473(3) N3 H3 0.8701 N3 C5 1.489(4) N3 C6 1.449(4) N4 H4 0.8700 N4 C7 1.518(4) N4 C8 1.442(3) N5 H5 0.8698 N5 C10 1.472(3) N5 C11 1.456(3) N6 C18 1.474(3) N6 C20 1.491(3) N6 C28 1.460(3) N7 H7 0.8700 N7 C26 1.469(3) N7 C27 1.455(3) N8 H8 0.8700 N8 C23 1.464(3) N8 C24 1.476(3) N9 H9 0.8700 N9 C21 1.457(3) N9 C22 1.486(3) C1 H1A 0.9900 C1 H1B 0.9900 C1 C2 1.509(4) C2 H2A 0.9900 C2 H2B 0.9900 C3 H3A 0.9900 C3 H3B 0.9900 C3 C4 1.505(4) C4 H4A 0.9900 C4 H4B 0.9900 C4 C5 1.511(4) C5 H5A 0.9900 C5 H5B 0.9900 C6 H6A 0.9900 C6 H6B 0.9900 C6 C7 1.498(4) C7 H7A 0.9900 C7 H7B 0.9900 C8 H8A 0.9900 C8 H8B 0.9900 C8 C9 1.503(4) C9 H9A 1.0000 C9 C10 1.557(4) C10 H10A 0.9900 C10 H10B 0.9900 C11 H11 1.0000 C11 C12 1.511(3) C12 C13 1.393(3) C12 C17 1.394(3) C13 H13 0.9500 C13 C14 1.380(4) C14 H14 0.9500 C14 C15 1.390(3) C15 H15 0.9500 C15 C16 1.397(3) C16 C17 1.390(3) C16 C18 1.507(3) C17 H17 0.9500 C18 H18 1.0000 C19 H19A 0.9900 C19 H19B 0.9900 C19 C20 1.549(4) C20 H20 1.0000 C20 C21 1.522(3) C21 H21A 0.9900 C21 H21B 0.9900 C22 H22A 0.9900 C22 H22B 0.9900 C22 C23 1.506(4) C23 H23A 0.9900 C23 H23B 0.9900 C24 H24A 0.9900 C24 H24B 0.9900 C24 C25 1.522(4) C25 H25A 0.9900 C25 H25B 0.9900 C25 C26 1.525(4) C26 H26A 0.9900 C26 H26B 0.9900 C27 H27A 0.9900 C27 H27B 0.9900 C27 C28 1.533(4) C28 H28A 0.9900 C28 H28B 0.9900 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1C N2 0.87 1.95 2.818(3) 175.9 1_455 O1 H1D N7 0.87 1.97 2.828(3) 171.0 . N2 H2 N3 0.88 2.37 3.018(3) 130.7 . N7 H7 N8 0.87 2.30 2.988(3) 135.6 . 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 N1 C1 C2 N2 60.7(3) N1 C9 C10 N5 -7.9(3) N1 C11 C12 C13 121.7(2) N1 C11 C12 C17 -59.5(3) N2 C3 C4 C5 -77.0(3) N10 C19 C20 N6 -6.8(3) N10 C19 C20 C21 113.0(2) N3 C6 C7 N4 56.7(3) N4 C8 C9 N1 62.1(3) N4 C8 C9 C10 -54.1(3) N5 C11 C12 C13 -119.5(2) N5 C11 C12 C17 59.3(3) N6 C20 C21 N9 62.0(3) N7 C27 C28 N6 61.5(3) N8 C24 C25 C26 60.0(3) N9 C22 C23 N8 58.4(3) C1 N1 C9 C8 94.7(3) C1 N1 C9 C10 -142.4(2) C1 N1 C11 N5 162.50(19) C1 N1 C11 C12 -74.3(2) C2 N2 C3 C4 -179.1(2) C3 N2 C2 C1 -176.9(2) C3 C4 C5 N3 59.1(3) C5 N3 C6 C7 172.2(2) C6 N3 C5 C4 71.2(3) C7 N4 C8 C9 -164.6(2) C8 N4 C7 C6 80.6(3) C8 C9 C10 N5 112.9(2) C9 N1 C1 C2 -139.5(2) C9 N1 C11 N5 34.6(2) C9 N1 C11 C12 157.77(19) C10 N5 C11 N1 -39.2(2) C10 N5 C11 C12 -162.35(19) C11 N1 C1 C2 97.7(2) C11 N1 C9 C8 -138.7(2) C11 N1 C9 C10 -15.8(2) C11 N5 C10 C9 28.8(2) C11 C12 C13 C14 -179.8(2) C11 C12 C17 C16 -178.9(2) C12 C13 C14 C15 -1.2(3) C13 C12 C17 C16 0.0(3) C13 C14 C15 C16 -0.2(3) C14 C15 C16 C17 1.5(3) C14 C15 C16 C18 -175.7(2) C15 C16 C17 C12 -1.4(3) C15 C16 C18 N10 -122.2(2) C15 C16 C18 N6 118.7(2) C17 C12 C13 C14 1.3(3) C17 C16 C18 N10 60.7(3) C17 C16 C18 N6 -58.4(3) C18 N10 C19 C20 27.0(2) C18 N6 C20 C19 -15.9(2) C18 N6 C20 C21 -138.2(2) C18 N6 C28 C27 97.5(2) C18 C16 C17 C12 175.8(2) C19 N10 C18 N6 -37.4(2) C19 N10 C18 C16 -159.64(18) C19 C20 C21 N9 -54.0(3) C20 N6 C18 N10 33.6(2) C20 N6 C18 C16 157.15(18) C20 N6 C28 C27 -137.8(2) C21 N9 C22 C23 78.1(3) C22 N9 C21 C20 -167.97(19) C23 N8 C24 C25 72.4(3) C24 N8 C23 C22 172.7(2) C24 C25 C26 N7 -76.7(3) C26 N7 C27 C28 178.7(2) C27 N7 C26 C25 -176.7(2) C28 N6 C18 N10 163.37(18) C28 N6 C18 C16 -73.1(2) C28 N6 C20 C19 -144.9(2) C28 N6 C20 C21 92.8(2)