#------------------------------------------------------------------------------ #$Date: 2017-05-31 07:50:14 +0300 (Wed, 31 May 2017) $ #$Revision: 197067 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/83/7228347.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_7228347 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 'C18 H27 N5 O' _chemical_formula_sum 'C18 H27 N5 O' _chemical_formula_weight 329.44 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2016-03-31 _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 114.6840(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.2517(5) _cell_length_b 12.3383(4) _cell_length_c 12.0306(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 1787.31(11) _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 0.998 _diffrn_measured_fraction_theta_max 0.994 _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 0.0656 _diffrn_reflns_av_unetI/netI 0.0621 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 14520 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.562 _diffrn_reflns_theta_min 2.363 _diffrn_source 'X-ray tube' _diffrn_source_target Mo _diffrn_source_type 'Siemens KFF Mo 2K-180' _exptl_absorpt_coefficient_mu 0.079 _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 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 712 _exptl_crystal_recrystallization_method 'The material was recrystallised from hexane by slow evaporation' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.176 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 226 _refine_ls_number_reflns 4104 _refine_ls_number_restraints 24 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.1066 _refine_ls_R_factor_gt 0.0507 _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^)+(0.0412P)^2^+0.4008P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1009 _refine_ls_wR_factor_ref 0.1180 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2485 _reflns_number_total 4104 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 07ns401.res created by SHELXL-2014/7 TITL 07ns401 in P 21/a New: P21/c CELL 0.71073 13.2517 12.3383 12.0306 90 114.684 90 ZERR 4 0.0005 0.0004 0.0004 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 72 108 20 4 EQIV $1 1-X,-Y,1-Z RIGU L.S. 10 PLAN 20 SIZE 0.1 0.1 0.2 TEMP -158(2) HTAB N2 N3 HTAB N3 N2_$1 HTAB N4 N1 HTAB N4 N3 HTAB 2.00000 BOND $H MORE -1 CONF fmap 2 acta MERG 2 OMIT 1 0 0 OMIT -1 1 1 OMIT 0 1 1 OMIT -7 0 4 OMIT 0 0 6 REM REM REM WGHT 0.041200 0.400800 FVAR 0.44699 C1 1 0.245436 -0.196150 0.270407 11.00000 0.03372 0.03378 = 0.03609 -0.00765 0.01407 -0.00411 AFIX 23 H1A 2 0.276178 -0.173296 0.211915 11.00000 -1.20000 H1B 2 0.184635 -0.248254 0.227840 11.00000 -1.20000 AFIX 0 C2 1 0.335671 -0.252631 0.377761 11.00000 0.03977 0.03148 = 0.03936 -0.00077 0.02027 -0.00226 AFIX 23 H2A 2 0.302704 -0.285513 0.430018 11.00000 -1.20000 H2B 2 0.367745 -0.311710 0.347017 11.00000 -1.20000 AFIX 0 C3 1 0.506390 -0.232927 0.557765 11.00000 0.03431 0.04667 = 0.04826 0.01511 0.01382 0.00634 AFIX 23 H3A 2 0.550828 -0.282241 0.530925 11.00000 -1.20000 H3B 2 0.467944 -0.277557 0.596614 11.00000 -1.20000 AFIX 0 C4 1 0.583755 -0.154438 0.651499 11.00000 0.02652 0.05871 = 0.04163 0.01844 0.00751 0.00200 AFIX 23 H4A 2 0.616079 -0.104885 0.610312 11.00000 -1.20000 H4B 2 0.645533 -0.195850 0.713754 11.00000 -1.20000 AFIX 0 C5 1 0.527864 -0.087306 0.715585 11.00000 0.03580 0.05800 = 0.03294 0.01131 0.00633 -0.00860 AFIX 23 H5A 2 0.481829 -0.135407 0.741476 11.00000 -1.20000 H5B 2 0.585510 -0.054233 0.789981 11.00000 -1.20000 AFIX 0 C6 1 0.392117 0.057542 0.689189 11.00000 0.04751 0.04807 = 0.02582 -0.00429 0.00929 -0.00912 AFIX 23 H6A 2 0.391578 0.135695 0.670311 11.00000 -1.20000 H6B 2 0.426919 0.049061 0.779244 11.00000 -1.20000 AFIX 0 C7 1 0.273870 0.015782 0.638904 11.00000 0.04220 0.05375 = 0.02735 -0.00301 0.01404 -0.00008 AFIX 23 H7A 2 0.274318 -0.063911 0.648675 11.00000 -1.20000 H7B 2 0.234682 0.048097 0.685180 11.00000 -1.20000 AFIX 0 C8 1 0.119850 -0.024980 0.441097 11.00000 0.02833 0.07535 = 0.03459 -0.01112 0.01653 -0.00060 AFIX 13 H8 2 0.084646 -0.046056 0.497018 11.00000 -1.20000 AFIX 0 C9 1 0.152149 -0.128538 0.394516 11.00000 0.03029 0.05703 = 0.03937 -0.01004 0.01825 -0.01557 AFIX 23 H9A 2 0.207506 -0.169348 0.464144 11.00000 -1.20000 H9B 2 0.085857 -0.175024 0.354187 11.00000 -1.20000 AFIX 0 C10 1 0.034614 0.037123 0.334151 11.00000 0.03186 0.11638 = 0.03839 -0.01648 0.01101 0.02327 AFIX 23 H10A 2 -0.037360 -0.001647 0.302249 11.00000 -1.20000 H10B 2 0.023381 0.110071 0.361360 11.00000 -1.20000 AFIX 0 C11 1 0.112178 -0.049329 0.198318 11.00000 0.02093 0.04875 = 0.02928 -0.01267 0.00567 -0.00159 AFIX 13 H11 2 0.049197 -0.100792 0.157095 11.00000 -1.20000 AFIX 0 C12 1 0.097363 0.140961 0.195850 11.00000 0.03654 0.05770 = 0.03557 -0.01469 -0.01028 0.02465 C13 1 0.144493 0.109618 0.108657 11.00000 0.02891 0.03740 = 0.03286 -0.00696 -0.00683 0.00769 C14 1 0.150654 -0.002071 0.106572 11.00000 0.01996 0.03833 = 0.02647 -0.00619 0.00144 0.00078 C15 1 0.183491 -0.051411 0.023312 11.00000 0.03276 0.03584 = 0.03210 -0.00250 0.00932 0.00280 AFIX 43 H15 2 0.184726 -0.128158 0.017656 11.00000 -1.20000 AFIX 0 C16 1 0.214460 0.013293 -0.051459 11.00000 0.03771 0.05159 = 0.03641 0.00582 0.01248 0.00555 AFIX 43 H16 2 0.238449 -0.019984 -0.107464 11.00000 -1.20000 AFIX 0 C17 1 0.211249 0.124140 -0.046406 11.00000 0.03892 0.05196 = 0.04359 0.01078 0.00389 -0.00275 AFIX 43 H17 2 0.234137 0.166468 -0.097735 11.00000 -1.20000 AFIX 0 C18 1 0.174963 0.174965 0.032805 11.00000 0.03951 0.03469 = 0.04675 0.00317 -0.00959 0.00146 AFIX 43 H18 2 0.170898 0.251728 0.035533 11.00000 -1.20000 AFIX 0 N1 3 0.199561 -0.100858 0.306274 11.00000 0.02220 0.03743 = 0.02804 -0.00651 0.01076 -0.00112 N2 3 0.423387 -0.178444 0.450618 11.00000 0.02757 0.03243 = 0.03703 0.00582 0.01143 0.00196 AFIX 2 H2 2 0.397988 -0.123029 0.477401 11.00000 -1.20000 AFIX 0 N3 3 0.457376 -0.001121 0.636601 11.00000 0.03229 0.04333 = 0.03025 0.00533 0.00910 -0.00939 AFIX 2 H3 2 0.498435 0.046794 0.617230 11.00000 -1.20000 AFIX 0 N4 3 0.215858 0.043813 0.509807 11.00000 0.03541 0.04921 = 0.02670 -0.00500 0.01220 0.00509 AFIX 2 H4 2 0.264378 0.032832 0.475820 11.00000 -1.20000 AFIX 0 N5 3 0.073877 0.046791 0.239125 11.00000 0.03159 0.06803 = 0.03139 -0.01155 0.00541 0.02073 O1 4 0.079854 0.233247 0.222742 11.00000 0.07142 0.06726 = 0.05213 -0.02243 -0.00920 0.04447 HKLF 4 1 0 0 1 0 -1 0 1 0 0 REM 07ns401 in P 21/a New: P21/c REM R1 = 0.0507 for 2485 Fo > 4sig(Fo) and 0.1066 for all 4104 data REM 226 parameters refined using 192 restraints END WGHT 0.0412 0.4008 REM Instructions for potential hydrogen bonds EQIV $2 -x, y-1/2, -z+1/2 HTAB C9 O1_$2 HTAB N2 N3 HTAB N3 N2_$1 HTAB N4 N1 HTAB N4 N3 REM Highest difference peak 0.176, deepest hole -0.184, 1-sigma level 0.038 Q1 1 0.0253 0.2203 0.2711 11.00000 0.05 0.18 Q2 1 0.4349 -0.0407 0.5454 11.00000 0.05 0.16 Q3 1 0.0534 0.1600 0.3629 11.00000 0.05 0.15 Q4 1 0.0992 -0.2163 0.3801 11.00000 0.05 0.14 Q5 1 0.0614 0.2314 -0.0855 11.00000 0.05 0.14 Q6 1 0.1442 0.1294 0.0566 11.00000 0.05 0.14 Q7 1 0.1388 0.1290 0.6533 11.00000 0.05 0.12 Q8 1 0.0786 -0.1987 -0.0755 11.00000 0.05 0.12 Q9 1 0.1571 -0.0651 0.2608 11.00000 0.05 0.12 Q10 1 0.1376 0.2335 0.0778 11.00000 0.05 0.12 Q11 1 0.1232 -0.1271 -0.0113 11.00000 0.05 0.12 Q12 1 0.2420 -0.0502 0.3589 11.00000 0.05 0.12 Q13 1 0.1240 -0.2428 0.1834 11.00000 0.05 0.12 Q14 1 0.1156 0.2687 0.3226 11.00000 0.05 0.11 Q15 1 0.6192 -0.2872 0.4213 11.00000 0.05 0.11 Q16 1 0.3235 -0.1327 0.7397 11.00000 0.05 0.11 Q17 1 0.2279 -0.0660 0.1339 11.00000 0.05 0.11 Q18 1 0.3049 -0.0583 0.1131 11.00000 0.05 0.11 Q19 1 0.1330 0.2077 0.3411 11.00000 0.05 0.11 Q20 1 -0.0440 -0.0697 0.3044 11.00000 0.05 0.11 REM The information below was added by Olex2. REM REM R1 = 0.0507 for 2485 Fo > 4sig(Fo) and 0.1066 for all 14910 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.18, deepest hole -0.18 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1066 REM R1_gt = 0.0507 REM wR_ref = 0.1180 REM GOOF = 1.022 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 14910 REM Reflections_gt = 2485 REM Parameters = n/a REM Hole = -0.18 REM Peak = 0.18 REM Flack = n/a ; _cod_data_source_file c7ra04218c2.cif _cod_data_source_block compound_12 _cod_database_code 7228347 _publcif_datablock.id {2dce831f-99e8-4974-ad19-540f259f3a8c} _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 0.992 _shelx_estimated_absorpt_t_min 0.984 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2. Rigid body (RIGU) restrains All non-hydrogen atoms with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 3.a Fixed occupancy and ADP/Uiso: H2, H3, H4 3.b Ternary CH refined with riding coordinates: C8(H8), C11(H11) 3.c 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), C9(H9A,H9B), C10(H10A,H10B) 3.d Aromatic/amide H refined with riding coordinates: C15(H15), C16(H16), C17(H17), C18(H18) ; _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 oil' _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp C1 C 0.24544(13) -0.19615(14) 0.27041(15) 0.0347(4) Uani 1 1 d . U H1A H 0.2762 -0.1733 0.2119 0.042 Uiso 1 1 calc R . H1B H 0.1846 -0.2483 0.2278 0.042 Uiso 1 1 calc R . C2 C 0.33567(13) -0.25263(14) 0.37776(15) 0.0356(4) Uani 1 1 d . U H2A H 0.3027 -0.2855 0.4300 0.043 Uiso 1 1 calc R . H2B H 0.3677 -0.3117 0.3470 0.043 Uiso 1 1 calc R . C3 C 0.50639(14) -0.23293(15) 0.55777(17) 0.0442(5) Uani 1 1 d . U H3A H 0.5508 -0.2822 0.5309 0.053 Uiso 1 1 calc R . H3B H 0.4679 -0.2776 0.5966 0.053 Uiso 1 1 calc R . C4 C 0.58375(14) -0.15444(16) 0.65150(16) 0.0445(5) Uani 1 1 d . U H4A H 0.6161 -0.1049 0.6103 0.053 Uiso 1 1 calc R . H4B H 0.6455 -0.1958 0.7138 0.053 Uiso 1 1 calc R . C5 C 0.52786(15) -0.08731(16) 0.71558(16) 0.0450(5) Uani 1 1 d . U H5A H 0.4818 -0.1354 0.7415 0.054 Uiso 1 1 calc R . H5B H 0.5855 -0.0542 0.7900 0.054 Uiso 1 1 calc R . C6 C 0.39212(15) 0.05754(16) 0.68919(16) 0.0425(5) Uani 1 1 d . U H6A H 0.3916 0.1357 0.6703 0.051 Uiso 1 1 calc R . H6B H 0.4269 0.0491 0.7792 0.051 Uiso 1 1 calc R . C7 C 0.27387(15) 0.01578(16) 0.63890(15) 0.0413(5) Uani 1 1 d . U H7A H 0.2743 -0.0639 0.6487 0.050 Uiso 1 1 calc R . H7B H 0.2347 0.0481 0.6852 0.050 Uiso 1 1 calc R . C8 C 0.11985(14) -0.02498(17) 0.44110(17) 0.0449(5) Uani 1 1 d . U H8 H 0.0846 -0.0461 0.4970 0.054 Uiso 1 1 calc R . C9 C 0.15215(14) -0.12854(15) 0.39452(16) 0.0410(5) Uani 1 1 d . U H9A H 0.2075 -0.1693 0.4641 0.049 Uiso 1 1 calc R . H9B H 0.0859 -0.1750 0.3542 0.049 Uiso 1 1 calc R . C10 C 0.03461(16) 0.0371(2) 0.33415(17) 0.0634(7) Uani 1 1 d . U H10A H -0.0374 -0.0016 0.3022 0.076 Uiso 1 1 calc R . H10B H 0.0234 0.1101 0.3614 0.076 Uiso 1 1 calc R . C11 C 0.11218(13) -0.04933(15) 0.19832(15) 0.0346(4) Uani 1 1 d . U H11 H 0.0492 -0.1008 0.1571 0.042 Uiso 1 1 calc R . C12 C 0.09736(15) 0.14096(19) 0.19585(17) 0.0518(6) Uani 1 1 d . U C13 C 0.14449(14) 0.10962(15) 0.10866(16) 0.0397(5) Uani 1 1 d . U C14 C 0.15065(12) -0.00207(14) 0.10657(14) 0.0310(4) Uani 1 1 d . U C15 C 0.18349(13) -0.05141(14) 0.02331(15) 0.0350(4) Uani 1 1 d . U H15 H 0.1847 -0.1282 0.0177 0.042 Uiso 1 1 calc R . C16 C 0.21446(15) 0.01329(16) -0.05146(16) 0.0429(5) Uani 1 1 d . U H16 H 0.2384 -0.0200 -0.1075 0.051 Uiso 1 1 calc R . C17 C 0.21125(15) 0.12414(17) -0.04641(18) 0.0493(5) Uani 1 1 d . U H17 H 0.2341 0.1665 -0.0977 0.059 Uiso 1 1 calc R . C18 C 0.17496(15) 0.17496(16) 0.03281(18) 0.0496(5) Uani 1 1 d . U H18 H 0.1709 0.2517 0.0355 0.060 Uiso 1 1 calc R . N1 N 0.19956(10) -0.10086(11) 0.30627(12) 0.0291(3) Uani 1 1 d . U N2 N 0.42339(11) -0.17844(12) 0.45062(13) 0.0330(3) Uani 1 1 d . U H2 H 0.3980(14) -0.1230(14) 0.4774(16) 0.040 Uiso 1 1 d . . N3 N 0.45738(12) -0.00112(13) 0.63660(12) 0.0366(4) Uani 1 1 d . U H3 H 0.4984(15) 0.0468(14) 0.6172(16) 0.044 Uiso 1 1 d . . N4 N 0.21586(12) 0.04381(12) 0.50981(13) 0.0374(4) Uani 1 1 d . U H4 H 0.2644(15) 0.0328(14) 0.4758(16) 0.045 Uiso 1 1 d . . N5 N 0.07388(12) 0.04679(15) 0.23912(13) 0.0463(4) Uani 1 1 d . U O1 O 0.07985(12) 0.23325(12) 0.22274(13) 0.0754(5) Uani 1 1 d . U 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 C1 0.0337(9) 0.0338(10) 0.0361(10) -0.0076(8) 0.0141(8) -0.0041(8) C2 0.0398(10) 0.0315(10) 0.0394(10) -0.0008(8) 0.0203(8) -0.0023(8) C3 0.0343(9) 0.0467(12) 0.0483(11) 0.0151(9) 0.0138(9) 0.0063(9) C4 0.0265(9) 0.0587(13) 0.0416(11) 0.0184(9) 0.0075(8) 0.0020(9) C5 0.0358(10) 0.0580(13) 0.0329(10) 0.0113(9) 0.0063(8) -0.0086(9) C6 0.0475(11) 0.0481(12) 0.0258(9) -0.0043(8) 0.0093(8) -0.0091(9) C7 0.0422(10) 0.0538(12) 0.0273(9) -0.0030(9) 0.0140(8) -0.0001(9) C8 0.0283(9) 0.0753(14) 0.0346(10) -0.0111(9) 0.0165(8) -0.0006(9) C9 0.0303(9) 0.0570(12) 0.0394(10) -0.0100(9) 0.0182(8) -0.0156(9) C10 0.0319(10) 0.116(2) 0.0384(11) -0.0165(12) 0.0110(9) 0.0233(12) C11 0.0209(8) 0.0487(11) 0.0293(9) -0.0127(8) 0.0057(7) -0.0016(8) C12 0.0365(10) 0.0577(13) 0.0356(11) -0.0147(10) -0.0103(8) 0.0246(10) C13 0.0289(9) 0.0374(11) 0.0329(10) -0.0070(8) -0.0068(8) 0.0077(8) C14 0.0200(8) 0.0383(10) 0.0265(9) -0.0062(8) 0.0014(7) 0.0008(7) C15 0.0328(9) 0.0358(10) 0.0321(9) -0.0025(8) 0.0093(8) 0.0028(8) C16 0.0377(10) 0.0516(12) 0.0364(10) 0.0058(9) 0.0125(9) 0.0056(9) C17 0.0389(11) 0.0520(13) 0.0436(12) 0.0108(10) 0.0039(9) -0.0028(9) C18 0.0395(10) 0.0347(11) 0.0467(12) 0.0032(9) -0.0096(9) 0.0015(9) N1 0.0222(6) 0.0374(8) 0.0280(7) -0.0065(6) 0.0108(6) -0.0011(6) N2 0.0276(7) 0.0324(8) 0.0370(8) 0.0058(7) 0.0114(6) 0.0020(6) N3 0.0323(8) 0.0433(9) 0.0302(8) 0.0053(7) 0.0091(7) -0.0094(7) N4 0.0354(8) 0.0492(10) 0.0267(8) -0.0050(7) 0.0122(7) 0.0051(7) N5 0.0316(8) 0.0680(12) 0.0314(9) -0.0115(8) 0.0054(7) 0.0207(8) O1 0.0714(10) 0.0673(10) 0.0521(9) -0.0224(8) -0.0092(7) 0.0445(8) 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 H1A C1 H1B 107.7 C2 C1 H1A 108.9 C2 C1 H1B 108.9 N1 C1 H1A 108.9 N1 C1 H1B 108.9 N1 C1 C2 113.21(13) C1 C2 H2A 109.2 C1 C2 H2B 109.2 H2A C2 H2B 107.9 N2 C2 C1 111.89(14) N2 C2 H2A 109.2 N2 C2 H2B 109.2 H3A C3 H3B 107.8 C4 C3 H3A 109.0 C4 C3 H3B 109.0 N2 C3 H3A 109.0 N2 C3 H3B 109.0 N2 C3 C4 112.85(15) C3 C4 H4A 108.8 C3 C4 H4B 108.8 C3 C4 C5 113.87(14) H4A C4 H4B 107.7 C5 C4 H4A 108.8 C5 C4 H4B 108.8 C4 C5 H5A 109.1 C4 C5 H5B 109.1 H5A C5 H5B 107.9 N3 C5 C4 112.27(15) N3 C5 H5A 109.1 N3 C5 H5B 109.1 H6A C6 H6B 108.0 C7 C6 H6A 109.4 C7 C6 H6B 109.4 N3 C6 H6A 109.4 N3 C6 H6B 109.4 N3 C6 C7 111.08(14) C6 C7 H7A 109.7 C6 C7 H7B 109.7 H7A C7 H7B 108.2 N4 C7 C6 110.00(15) N4 C7 H7A 109.7 N4 C7 H7B 109.7 C9 C8 H8 108.1 C10 C8 H8 108.1 C10 C8 C9 109.56(15) N4 C8 H8 108.1 N4 C8 C9 112.44(14) N4 C8 C10 110.45(17) C8 C9 H9A 109.7 C8 C9 H9B 109.7 H9A C9 H9B 108.2 N1 C9 C8 109.75(15) N1 C9 H9A 109.7 N1 C9 H9B 109.7 C8 C10 H10A 109.9 C8 C10 H10B 109.9 H10A C10 H10B 108.3 N5 C10 C8 109.02(14) N5 C10 H10A 109.9 N5 C10 H10B 109.9 C14 C11 H11 110.4 N1 C11 H11 110.4 N1 C11 C14 115.39(12) N5 C11 H11 110.4 N5 C11 C14 101.75(15) N5 C11 N1 108.10(13) N5 C12 C13 106.25(16) O1 C12 C13 127.6(2) O1 C12 N5 126.2(2) C14 C13 C12 108.63(18) C14 C13 C18 121.89(18) C18 C13 C12 129.42(18) C13 C14 C11 109.32(15) C13 C14 C15 119.29(17) C15 C14 C11 131.31(16) C14 C15 H15 120.6 C16 C15 C14 118.84(17) C16 C15 H15 120.6 C15 C16 H16 119.2 C17 C16 C15 121.51(18) C17 C16 H16 119.2 C16 C17 H17 119.7 C16 C17 C18 120.59(19) C18 C17 H17 119.7 C13 C18 H18 121.1 C17 C18 C13 117.80(18) C17 C18 H18 121.1 C1 N1 C9 112.17(13) C1 N1 C11 110.82(12) C11 N1 C9 108.56(12) C2 N2 C3 111.12(14) C2 N2 H2 112.2(11) C3 N2 H2 107.2(11) C5 N3 H3 110.7(11) C6 N3 C5 114.20(14) C6 N3 H3 108.6(12) C7 N4 C8 114.28(15) C7 N4 H4 106.7(11) C8 N4 H4 105.8(11) C10 N5 C11 119.45(18) C12 N5 C10 126.04(17) C12 N5 C11 113.54(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 H1A 0.9900 C1 H1B 0.9900 C1 C2 1.514(2) C1 N1 1.469(2) C2 H2A 0.9900 C2 H2B 0.9900 C2 N2 1.451(2) C3 H3A 0.9900 C3 H3B 0.9900 C3 C4 1.515(3) C3 N2 1.463(2) C4 H4A 0.9900 C4 H4B 0.9900 C4 C5 1.519(3) C5 H5A 0.9900 C5 H5B 0.9900 C5 N3 1.471(2) C6 H6A 0.9900 C6 H6B 0.9900 C6 C7 1.515(2) C6 N3 1.459(2) C7 H7A 0.9900 C7 H7B 0.9900 C7 N4 1.458(2) C8 H8 1.0000 C8 C9 1.526(3) C8 C10 1.518(3) C8 N4 1.464(2) C9 H9A 0.9900 C9 H9B 0.9900 C9 N1 1.482(2) C10 H10A 0.9900 C10 H10B 0.9900 C10 N5 1.445(2) C11 H11 1.0000 C11 C14 1.513(2) C11 N1 1.475(2) C11 N5 1.454(2) C12 C13 1.479(3) C12 N5 1.361(3) C12 O1 1.232(2) C13 C14 1.381(2) C13 C18 1.398(3) C14 C15 1.388(2) C15 H15 0.9500 C15 C16 1.387(2) C16 H16 0.9500 C16 C17 1.370(3) C17 H17 0.9500 C17 C18 1.384(3) C18 H18 0.9500 N2 H2 0.880(18) N3 H3 0.898(18) N4 H4 0.905(19) 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 N2 H2 N3 0.880(18) 2.300(18) 3.026(2) 139.7(15) . N3 H3 N2 0.898(18) 2.255(19) 3.145(2) 171.3(16) 3_656 N4 H4 N1 0.905(19) 2.481(18) 2.9643(19) 113.8(14) . N4 H4 N3 0.905(19) 2.515(18) 2.966(2) 111.3(13) . 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 C1 C2 N2 C3 176.66(14) C2 C1 N1 C9 -58.42(17) C2 C1 N1 C11 -179.93(13) C3 C4 C5 N3 -74.80(19) C4 C3 N2 C2 -166.31(15) C4 C5 N3 C6 173.36(14) C6 C7 N4 C8 157.60(15) C7 C6 N3 C5 -99.23(17) C8 C9 N1 C1 172.59(13) C8 C9 N1 C11 -64.62(16) C8 C10 N5 C11 50.2(2) C8 C10 N5 C12 -117.7(2) C9 C8 C10 N5 -49.4(2) C9 C8 N4 C7 -85.34(18) C10 C8 C9 N1 59.61(18) C10 C8 N4 C7 151.93(15) C11 C14 C15 C16 179.56(15) C12 C13 C14 C11 -2.68(17) C12 C13 C14 C15 174.48(14) C12 C13 C18 C17 -176.16(16) C13 C12 N5 C10 174.73(14) C13 C12 N5 C11 6.22(18) C13 C14 C15 C16 3.1(2) C14 C11 N1 C1 -64.38(18) C14 C11 N1 C9 172.01(14) C14 C11 N5 C10 -176.87(14) C14 C11 N5 C12 -7.53(17) C14 C13 C18 C17 0.5(2) C14 C15 C16 C17 -1.3(3) C15 C16 C17 C18 -1.1(3) C16 C17 C18 C13 1.4(3) C18 C13 C14 C11 -179.95(14) C18 C13 C14 C15 -2.8(2) N1 C1 C2 N2 -53.79(18) N1 C11 C14 C13 -110.80(15) N1 C11 C14 C15 72.5(2) N1 C11 N5 C10 -54.96(19) N1 C11 N5 C12 114.38(15) N2 C3 C4 C5 68.6(2) N3 C6 C7 N4 -68.4(2) N4 C8 C9 N1 -63.62(19) N4 C8 C10 N5 74.9(2) N5 C11 C14 C13 5.94(16) N5 C11 C14 C15 -170.76(16) N5 C11 N1 C1 -177.47(14) N5 C11 N1 C9 58.92(17) N5 C12 C13 C14 -1.99(18) N5 C12 C13 C18 175.01(16) O1 C12 C13 C14 179.59(17) O1 C12 C13 C18 -3.4(3) O1 C12 N5 C10 -6.8(3) O1 C12 N5 C11 -175.34(16)