#------------------------------------------------------------------------------ #$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $ #$Revision: 288505 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/22/7222298.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_7222298 loop_ _publ_author_name 'Camus, Nathalie' 'Halme, Zakaria' 'Nathalie, Le Bris' 'Bernard, H\'el\`ene' 'Beyler, Maryline' 'Platas-Iglesias, Carlos' 'Tripier, Raphael' _publ_section_title ; A [Two-Steps / One Week] Synthesis of C-Functionalized Homocyclens and Cyclams. Application to the Preparation of Conjugable BCAs without Chelating Properties Alteration ; _journal_name_full 'RSC Adv.' _journal_paper_doi 10.1039/C5RA17133D _journal_year 2015 _chemical_formula_moiety 'C16 H28 N4 O2' _chemical_formula_sum 'C16 H28 N4 O2' _chemical_formula_weight 308.42 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2012-05-24T15:05:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2015-07-13 deposited with the CCDC. 2015-09-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.795(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.9879(5) _cell_length_b 19.2936(13) _cell_length_c 13.5403(9) _cell_measurement_reflns_used 2114 _cell_measurement_temperature 170(2) _cell_measurement_theta_max 31.6457 _cell_measurement_theta_min 3.0021 _cell_volume 1564.1(2) _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX (Farrugia, 1999) PLATON (Spek, 1990-2003) PARST (Nardelli, 1999) enCIFer (Allen et al., 2004) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 170(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.3622 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'Kappa-geometry diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0136334901 _diffrn_orient_matrix_UB_12 0.0284068581 _diffrn_orient_matrix_UB_13 0.0326144649 _diffrn_orient_matrix_UB_21 0.0131611421 _diffrn_orient_matrix_UB_22 0.0233566082 _diffrn_orient_matrix_UB_23 -0.0399587035 _diffrn_orient_matrix_UB_31 -0.1169603847 _diffrn_orient_matrix_UB_32 -0.0006575053 _diffrn_orient_matrix_UB_33 -0.0090785539 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0925 _diffrn_reflns_av_unetI/netI 0.1378 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 13412 _diffrn_reflns_theta_full 28.27 _diffrn_reflns_theta_max 28.27 _diffrn_reflns_theta_min 3.19 _diffrn_source 'sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 0.9982 _exptl_absorpt_correction_T_min 0.9772 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.31 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'planar // (0 1 0)' _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.201 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 204 _refine_ls_number_reflns 3861 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.842 _refine_ls_R_factor_all 0.1647 _refine_ls_R_factor_gt 0.0534 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0289P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.0903 _reflns_number_gt 1649 _reflns_number_total 3861 _reflns_threshold_expression >2\s(I) _iucr_refine_instructions_details ; TITL NC193ter-b at 170 K in P2(1)/n (#14 in standard setting) CELL 0.71073 5.9879 19.2936 13.5403 90.000 90.795 90.000 ZERR 4.00 0.0005 0.0013 0.0009 0.000 0.007 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 64 112 16 8 MERG 2 OMIT 0 0 2 SHEL 13 0.75 EQIV $1 -x+1, -y, -z+1 HTAB O2 O1_$1 FMAP 2 PLAN 20 SIZE 0.02 0.29 0.29 ACTA BOND $H L.S. 4 TEMP -103.00 WGHT 0.027600 FVAR 0.56802 MOLE 1 C1 1 0.250655 0.117997 0.503604 11.00000 0.01988 0.02747 = 0.02821 0.00450 0.00201 -0.00211 C2 1 0.217113 0.092993 0.398090 11.00000 0.03166 0.02588 = 0.02351 0.00000 0.00159 -0.00055 AFIX 13 H2 2 0.359686 0.102580 0.363003 11.00000 -1.20000 AFIX 0 C3 1 0.034068 0.132671 0.342639 11.00000 0.03995 0.03040 = 0.02659 -0.00313 -0.00513 0.00144 AFIX 23 H3A 2 0.053784 0.126017 0.270788 11.00000 -1.20000 H3B 2 -0.112812 0.112980 0.360183 11.00000 -1.20000 AFIX 0 C4 1 0.231987 0.239786 0.323280 11.00000 0.03675 0.03310 = 0.01579 0.00222 0.00245 0.00442 AFIX 23 H4A 2 0.238528 0.230142 0.251566 11.00000 -1.20000 H4B 2 0.367526 0.219948 0.355010 11.00000 -1.20000 AFIX 0 C5 1 0.227826 0.316556 0.339756 11.00000 0.02713 0.03672 = 0.02308 0.00436 0.00185 0.00185 AFIX 23 H5A 2 0.365029 0.337762 0.313174 11.00000 -1.20000 H5B 2 0.097508 0.337083 0.304756 11.00000 -1.20000 AFIX 0 C6 1 0.232118 0.405859 0.462090 11.00000 0.02954 0.02895 = 0.03637 0.00123 0.00188 0.00044 AFIX 23 H6A 2 0.111187 0.429918 0.425139 11.00000 -1.20000 H6B 2 0.376682 0.422598 0.436695 11.00000 -1.20000 AFIX 0 C7 1 0.216307 0.423534 0.571135 11.00000 0.04694 0.02625 = 0.04262 -0.00678 0.00139 -0.00017 AFIX 23 H7A 2 0.198116 0.474240 0.578825 11.00000 -1.20000 H7B 2 0.356452 0.409774 0.605478 11.00000 -1.20000 AFIX 0 C8 1 0.019872 0.386538 0.618185 11.00000 0.04944 0.03609 = 0.03931 -0.00956 0.00813 0.00379 AFIX 23 H8A 2 0.027460 0.393240 0.690642 11.00000 -1.20000 H8B 2 -0.121199 0.407503 0.593608 11.00000 -1.20000 AFIX 0 C9 1 0.210304 0.278612 0.643482 11.00000 0.03695 0.03858 = 0.01744 -0.00347 0.00211 -0.00320 AFIX 23 H9A 2 0.214280 0.290659 0.714556 11.00000 -1.20000 H9B 2 0.349113 0.296184 0.613488 11.00000 -1.20000 AFIX 0 C10 1 0.200052 0.201752 0.632305 11.00000 0.03529 0.03557 = 0.01777 -0.00021 -0.00027 -0.00030 AFIX 23 H10A 2 0.335656 0.180608 0.662166 11.00000 -1.20000 H10B 2 0.068492 0.183550 0.667400 11.00000 -1.20000 AFIX 0 C11 1 0.006188 0.219536 0.469202 11.00000 0.02152 0.02710 = 0.02296 -0.00062 -0.00137 0.00158 C12 1 0.011865 0.299987 0.488709 11.00000 0.01866 0.02969 = 0.02450 -0.00092 0.00252 0.00345 C13 1 0.180875 0.014910 0.393483 11.00000 0.03980 0.02872 = 0.03331 -0.00424 0.00464 -0.00071 AFIX 23 H13A 2 0.271957 -0.007439 0.446096 11.00000 -1.20000 H13B 2 0.021999 0.004779 0.406721 11.00000 -1.20000 AFIX 0 C14 1 0.241644 -0.016305 0.294905 11.00000 0.06164 0.03324 = 0.03997 -0.00329 -0.00048 0.00622 AFIX 23 H14A 2 0.199149 -0.065893 0.294412 11.00000 -1.20000 H14B 2 0.154702 0.007212 0.241979 11.00000 -1.20000 AFIX 0 C15 1 -0.218089 0.190377 0.503539 11.00000 0.02396 0.03576 = 0.04259 0.00050 0.00340 -0.00187 AFIX 137 H15A 2 -0.255062 0.210462 0.567748 11.00000 -1.50000 H15B 2 -0.207289 0.139873 0.509681 11.00000 -1.50000 H15C 2 -0.335185 0.202167 0.455122 11.00000 -1.50000 AFIX 0 C16 1 -0.205369 0.330353 0.444736 11.00000 0.02356 0.03191 = 0.05226 0.00064 -0.00006 0.00283 AFIX 137 H16A 2 -0.328574 0.321806 0.490046 11.00000 -1.50000 H16B 2 -0.238333 0.308210 0.381049 11.00000 -1.50000 H16C 2 -0.187536 0.380380 0.435112 11.00000 -1.50000 AFIX 0 N1 3 0.184131 0.183041 0.527461 11.00000 0.02359 0.02523 = 0.01721 -0.00081 -0.00083 0.00112 N2 3 0.033577 0.206825 0.364168 11.00000 0.02977 0.02543 = 0.02160 -0.00169 -0.00402 0.00020 N3 3 0.213792 0.330602 0.445135 11.00000 0.02250 0.02146 = 0.02335 0.00026 0.00144 -0.00030 N4 3 0.018012 0.311724 0.596195 11.00000 0.03145 0.02733 = 0.02902 -0.00487 0.00703 0.00318 O1 4 0.348789 0.081183 0.564376 11.00000 0.04760 0.03481 = 0.03279 0.00638 -0.00787 0.00956 O2 4 0.472492 -0.010534 0.274279 11.00000 0.06779 0.05131 = 0.03448 0.01187 0.01243 0.02264 H2O 2 0.550735 -0.035004 0.323303 11.00000 -1.50000 HKLF 4 REM NC193ter-b at 170 K in P2(1)/n (#14 in standard setting) REM R1 = 0.0534 for 1649 Fo > 4sig(Fo) and 0.1648 for all 3861 data REM 204 parameters refined using 0 restraints END WGHT 0.0275 0.0000 REM Highest difference peak 0.201, deepest hole -0.183, 1-sigma level 0.041 Q1 1 0.0029 0.2609 0.4714 11.00000 0.05 0.20 Q2 1 0.2777 0.2986 0.4961 11.00000 0.05 0.20 Q3 1 -0.0860 0.2820 0.6408 11.00000 0.05 0.17 Q4 1 0.1735 0.1021 0.4546 11.00000 0.05 0.16 Q5 1 -0.0025 0.3579 0.7013 11.00000 0.05 0.16 Q6 1 0.2238 0.2020 0.5670 11.00000 0.05 0.16 Q7 1 0.1438 0.1098 0.3799 11.00000 0.05 0.15 Q8 1 0.3432 0.5014 0.6040 11.00000 0.05 0.15 Q9 1 0.2535 0.0683 0.4471 11.00000 0.05 0.14 Q10 1 0.0961 0.3148 0.4558 11.00000 0.05 0.14 Q11 1 -0.1036 0.1207 0.2938 11.00000 0.05 0.14 Q12 1 -0.0948 0.3074 0.4637 11.00000 0.05 0.14 Q13 1 0.2686 0.1608 0.4988 11.00000 0.05 0.14 Q14 1 0.5021 0.4055 0.3584 11.00000 0.05 0.13 Q15 1 0.0806 0.2022 0.5031 11.00000 0.05 0.13 Q16 1 0.3946 0.0374 0.5725 11.00000 0.05 0.13 Q17 1 0.4317 0.3475 0.3391 11.00000 0.05 0.13 Q18 1 -0.0547 0.2106 0.3219 11.00000 0.05 0.13 Q19 1 0.2987 0.4554 0.5827 11.00000 0.05 0.13 Q20 1 0.0544 0.2993 0.5324 11.00000 0.05 0.13 ; _cod_data_source_file c5ra17133d2.cif _cod_data_source_block nc193ter-b _cod_depositor_comments ; The following automatic conversions were performed: '_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius The following automatic conversions were performed: data name '_iucr_refine_instruction_details' was replaced with '_iucr_refine_instructions_details' as specified in the replacement file 'data/replacement-values/replacement_tags.lst'. Automatic conversion script Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas ; _cod_original_sg_symbol_Hall -P2yn _cod_original_sg_symbol_H-M P21/n _cod_database_code 7222298 loop_ _symmetry_equiv_pos_as_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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags C1 C 0.2507(3) 0.11799(10) 0.50360(15) 0.0251(5) Uani 1 1 d . C2 C 0.2171(3) 0.09299(9) 0.39808(14) 0.0270(5) Uani 1 1 d . H2 H 0.3597 0.1026 0.363 0.032 Uiso 1 1 calc R C3 C 0.0341(4) 0.13267(10) 0.34263(15) 0.0323(5) Uani 1 1 d . H3A H 0.0538 0.126 0.2708 0.039 Uiso 1 1 calc R H3B H -0.1128 0.113 0.3602 0.039 Uiso 1 1 calc R C4 C 0.2320(3) 0.23979(10) 0.32328(13) 0.0285(5) Uani 1 1 d . H4A H 0.2386 0.2301 0.2516 0.034 Uiso 1 1 calc R H4B H 0.3676 0.22 0.355 0.034 Uiso 1 1 calc R C5 C 0.2278(3) 0.31655(10) 0.33975(13) 0.0289(5) Uani 1 1 d . H5A H 0.365 0.3378 0.3132 0.035 Uiso 1 1 calc R H5B H 0.0975 0.3371 0.3047 0.035 Uiso 1 1 calc R C6 C 0.2321(4) 0.40586(10) 0.46210(14) 0.0316(5) Uani 1 1 d . H6A H 0.1112 0.4299 0.4251 0.038 Uiso 1 1 calc R H6B H 0.3767 0.4226 0.4367 0.038 Uiso 1 1 calc R C7 C 0.2163(4) 0.42353(10) 0.57114(15) 0.0386(6) Uani 1 1 d . H7A H 0.1981 0.4742 0.5788 0.046 Uiso 1 1 calc R H7B H 0.3565 0.4098 0.6055 0.046 Uiso 1 1 calc R C8 C 0.0199(4) 0.38655(11) 0.61818(17) 0.0415(6) Uani 1 1 d . H8A H 0.0275 0.3933 0.6906 0.05 Uiso 1 1 calc R H8B H -0.1212 0.4075 0.5936 0.05 Uiso 1 1 calc R C9 C 0.2103(3) 0.27862(10) 0.64348(14) 0.0309(5) Uani 1 1 d . H9A H 0.2143 0.2907 0.7146 0.037 Uiso 1 1 calc R H9B H 0.3491 0.2962 0.6135 0.037 Uiso 1 1 calc R C10 C 0.2001(4) 0.20175(10) 0.63231(13) 0.0295(5) Uani 1 1 d . H10A H 0.3357 0.1806 0.6622 0.035 Uiso 1 1 calc R H10B H 0.0685 0.1836 0.6674 0.035 Uiso 1 1 calc R C11 C 0.0062(3) 0.21954(10) 0.46921(14) 0.0239(5) Uani 1 1 d . C12 C 0.0119(3) 0.29999(10) 0.48871(14) 0.0242(5) Uani 1 1 d . C13 C 0.1809(4) 0.01490(10) 0.39347(15) 0.0339(5) Uani 1 1 d . H13A H 0.272 -0.0074 0.4461 0.041 Uiso 1 1 calc R H13B H 0.022 0.0048 0.4067 0.041 Uiso 1 1 calc R C14 C 0.2417(4) -0.01630(12) 0.29491(15) 0.0449(6) Uani 1 1 d . H14A H 0.1992 -0.0659 0.2944 0.054 Uiso 1 1 calc R H14B H 0.1547 0.0072 0.242 0.054 Uiso 1 1 calc R C15 C -0.2181(3) 0.19037(10) 0.50354(15) 0.0340(5) Uani 1 1 d . H15A H -0.2551 0.2105 0.5677 0.051 Uiso 1 1 calc R H15B H -0.2073 0.1399 0.5097 0.051 Uiso 1 1 calc R H15C H -0.3352 0.2022 0.4551 0.051 Uiso 1 1 calc R C16 C -0.2054(3) 0.33035(10) 0.44473(16) 0.0359(6) Uani 1 1 d . H16A H -0.3286 0.3218 0.49 0.054 Uiso 1 1 calc R H16B H -0.2383 0.3082 0.381 0.054 Uiso 1 1 calc R H16C H -0.1876 0.3804 0.4351 0.054 Uiso 1 1 calc R N1 N 0.1841(3) 0.18304(8) 0.52747(11) 0.0220(4) Uani 1 1 d . N2 N 0.0336(3) 0.20682(8) 0.36417(11) 0.0256(4) Uani 1 1 d . N3 N 0.2138(3) 0.33060(8) 0.44513(11) 0.0224(4) Uani 1 1 d . N4 N 0.0180(3) 0.31173(8) 0.59620(12) 0.0292(4) Uani 1 1 d . O1 O 0.3488(2) 0.08118(7) 0.56437(10) 0.0385(4) Uani 1 1 d . O2 O 0.4725(3) -0.01054(8) 0.27428(11) 0.0510(5) Uani 1 1 d . H2O H 0.551(4) -0.0350(13) 0.3234(18) 0.077 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 C1 0.0199(11) 0.0274(12) 0.0282(12) 0.0045(10) 0.0020(10) -0.0021(10) C2 0.0317(13) 0.0259(12) 0.0235(11) 0.0000(10) 0.0016(10) -0.0006(10) C3 0.0399(14) 0.0304(13) 0.0266(12) -0.0031(10) -0.0052(11) 0.0014(11) C4 0.0367(13) 0.0331(13) 0.0158(10) 0.0022(10) 0.0024(10) 0.0044(11) C5 0.0271(12) 0.0367(13) 0.0230(12) 0.0044(10) 0.0018(10) 0.0019(11) C6 0.0296(13) 0.0289(12) 0.0363(13) 0.0012(11) 0.0019(10) 0.0005(11) C7 0.0470(15) 0.0262(12) 0.0426(14) -0.0068(12) 0.0014(12) -0.0002(12) C8 0.0494(16) 0.0360(14) 0.0393(13) -0.0096(12) 0.0081(12) 0.0037(12) C9 0.0368(14) 0.0386(13) 0.0174(11) -0.0035(10) 0.0021(10) -0.0032(11) C10 0.0353(14) 0.0355(13) 0.0178(11) -0.0002(10) -0.0003(10) -0.0003(11) C11 0.0215(11) 0.0271(11) 0.0230(11) -0.0006(10) -0.0014(9) 0.0016(10) C12 0.0186(11) 0.0297(12) 0.0245(11) -0.0009(10) 0.0026(9) 0.0034(10) C13 0.0397(14) 0.0287(12) 0.0333(12) -0.0042(11) 0.0046(11) -0.0007(11) C14 0.0616(18) 0.0332(14) 0.0399(15) -0.0033(12) -0.0004(13) 0.0062(13) C15 0.0239(12) 0.0357(13) 0.0426(13) 0.0005(11) 0.0034(10) -0.0019(11) C16 0.0235(12) 0.0319(12) 0.0522(15) 0.0006(12) 0.0000(11) 0.0028(11) N1 0.0236(10) 0.0253(9) 0.0172(9) -0.0008(8) -0.0008(7) 0.0011(8) N2 0.0298(10) 0.0254(10) 0.0216(9) -0.0017(8) -0.0040(8) 0.0002(8) N3 0.0225(10) 0.0214(9) 0.0234(9) 0.0003(8) 0.0014(8) -0.0003(8) N4 0.0314(11) 0.0273(10) 0.0290(10) -0.0048(9) 0.0070(8) 0.0032(9) O1 0.0476(10) 0.0348(8) 0.0328(9) 0.0064(8) -0.0079(8) 0.0095(8) O2 0.0678(13) 0.0512(11) 0.0344(9) 0.0119(8) 0.0125(9) 0.0226(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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.01 0 -1 0 0.01 0 0 1 0.14 0 0 -1 0.15 1 0 0 0.135 -1 0 0 0.155 -1 0 -3 0.18 1 0 8 0.15 -1 0 -1 0.16 1 2 -20 0.15 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 C1 N1 120.91(18) O1 C1 C2 120.11(17) N1 C1 C2 118.83(17) C1 C2 C3 112.85(16) C1 C2 C13 111.69(16) C3 C2 C13 112.03(17) C1 C2 H2 106.6 C3 C2 H2 106.6 C13 C2 H2 106.6 N2 C3 C2 113.38(16) N2 C3 H3A 108.9 C2 C3 H3A 108.9 N2 C3 H3B 108.9 C2 C3 H3B 108.9 H3A C3 H3B 107.7 N2 C4 C5 110.98(16) N2 C4 H4A 109.4 C5 C4 H4A 109.4 N2 C4 H4B 109.4 C5 C4 H4B 109.4 H4A C4 H4B 108 N3 C5 C4 109.35(16) N3 C5 H5A 109.8 C4 C5 H5A 109.8 N3 C5 H5B 109.8 C4 C5 H5B 109.8 H5A C5 H5B 108.3 N3 C6 C7 111.53(16) N3 C6 H6A 109.3 C7 C6 H6A 109.3 N3 C6 H6B 109.3 C7 C6 H6B 109.3 H6A C6 H6B 108 C6 C7 C8 111.11(18) C6 C7 H7A 109.4 C8 C7 H7A 109.4 C6 C7 H7B 109.4 C8 C7 H7B 109.4 H7A C7 H7B 108 N4 C8 C7 112.22(17) N4 C8 H8A 109.2 C7 C8 H8A 109.2 N4 C8 H8B 109.2 C7 C8 H8B 109.2 H8A C8 H8B 107.9 N4 C9 C10 111.11(17) N4 C9 H9A 109.4 C10 C9 H9A 109.4 N4 C9 H9B 109.4 C10 C9 H9B 109.4 H9A C9 H9B 108 N1 C10 C9 110.17(16) N1 C10 H10A 109.6 C9 C10 H10A 109.6 N1 C10 H10B 109.6 C9 C10 H10B 109.6 H10A C10 H10B 108.1 N2 C11 N1 110.34(15) N2 C11 C15 110.21(16) N1 C11 C15 106.75(15) N2 C11 C12 109.13(15) N1 C11 C12 111.26(15) C15 C11 C12 109.13(16) N4 C12 N3 108.91(15) N4 C12 C16 109.47(16) N3 C12 C16 112.68(16) N4 C12 C11 108.51(15) N3 C12 C11 110.08(15) C16 C12 C11 107.10(16) C14 C13 C2 113.19(18) C14 C13 H13A 108.9 C2 C13 H13A 108.9 C14 C13 H13B 108.9 C2 C13 H13B 108.9 H13A C13 H13B 107.8 O2 C14 C13 112.92(19) O2 C14 H14A 109 C13 C14 H14A 109 O2 C14 H14B 109 C13 C14 H14B 109 H14A C14 H14B 107.8 C11 C15 H15A 109.5 C11 C15 H15B 109.5 H15A C15 H15B 109.5 C11 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C12 C16 H16A 109.5 C12 C16 H16B 109.5 H16A C16 H16B 109.5 C12 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C1 N1 C10 116.28(16) C1 N1 C11 121.33(15) C10 N1 C11 115.57(15) C11 N2 C3 111.17(15) C11 N2 C4 113.57(15) C3 N2 C4 110.26(16) C5 N3 C6 109.33(15) C5 N3 C12 112.09(15) C6 N3 C12 113.05(15) C9 N4 C12 112.06(15) C9 N4 C8 109.69(16) C12 N4 C8 110.50(16) C14 O2 H2O 107.5(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.230(2) C1 N1 1.357(2) C1 C2 1.519(3) C2 C3 1.526(3) C2 C13 1.523(3) C2 H2 1 C3 N2 1.460(2) C3 H3A 0.99 C3 H3B 0.99 C4 N2 1.463(2) C4 C5 1.498(3) C4 H4A 0.99 C4 H4B 0.99 C5 N3 1.456(2) C5 H5A 0.99 C5 H5B 0.99 C6 N3 1.474(2) C6 C7 1.520(3) C6 H6A 0.99 C6 H6B 0.99 C7 C8 1.523(3) C7 H7A 0.99 C7 H7B 0.99 C8 N4 1.474(2) C8 H8A 0.99 C8 H8B 0.99 C9 N4 1.457(2) C9 C10 1.492(3) C9 H9A 0.99 C9 H9B 0.99 C10 N1 1.467(2) C10 H10A 0.99 C10 H10B 0.99 C11 N2 1.455(2) C11 N1 1.493(2) C11 C15 1.534(3) C11 C12 1.575(3) C12 N4 1.473(2) C12 N3 1.476(2) C12 C16 1.539(3) C13 C14 1.513(3) C13 H13A 0.99 C13 H13B 0.99 C14 O2 1.418(3) C14 H14A 0.99 C14 H14B 0.99 C15 H15A 0.98 C15 H15B 0.98 C15 H15C 0.98 C16 H16A 0.98 C16 H16B 0.98 C16 H16C 0.98 O2 H2O 0.93(2) 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 O2 H2O O1 0.93(2) 1.86(2) 2.777(2) 168(2) 3_656