#------------------------------------------------------------------------------ #$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $ #$Revision: 288505 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/22/7222299.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_7222299 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 'C15 H26 N4 O2' _chemical_formula_sum 'C15 H26 N4 O2' _chemical_formula_weight 294.4 _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 2012-10-15T18:04:01-00:00 _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 97.971(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.7908(8) _cell_length_b 10.4516(8) _cell_length_c 12.3326(8) _cell_measurement_reflns_used 2384 _cell_measurement_temperature 170(2) _cell_measurement_theta_max 31.6801 _cell_measurement_theta_min 2.9591 _cell_volume 1505.10(18) _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) enCIFer (Allen et al., 2004) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR-92 (Altomare et al., 1992)' _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 0.0157469091 _diffrn_orient_matrix_UB_12 -0.0375286364 _diffrn_orient_matrix_UB_13 -0.0433735937 _diffrn_orient_matrix_UB_21 0.0536520374 _diffrn_orient_matrix_UB_22 0.0315500391 _diffrn_orient_matrix_UB_23 0.0050501106 _diffrn_orient_matrix_UB_31 0.0235632541 _diffrn_orient_matrix_UB_32 -0.0467715848 _diffrn_orient_matrix_UB_33 0.038188314 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0622 _diffrn_reflns_av_unetI/netI 0.0875 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 10760 _diffrn_reflns_theta_full 25.68 _diffrn_reflns_theta_max 25.68 _diffrn_reflns_theta_min 2.97 _diffrn_source 'sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_correction_T_min 0.9795 _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 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangles, hygroscopic' _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.156 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.805 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 193 _refine_ls_number_reflns 2854 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.805 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0383 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.0701 _reflns_number_gt 1598 _reflns_number_total 2854 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL NC281-c at 170 K in P2(1)/n CELL 0.71073 11.7908 10.4516 12.3326 90.000 97.971 90.000 ZERR 4.00 0.0008 0.0008 0.0008 0.000 0.006 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 60 104 16 8 MERG 2 SHEL 15 0.82 EQIV $1 x+1/2, -y+1/2, z-1/2 HTAB O2 N4_$1 FMAP 2 PLAN 25 SIZE 0.05 0.08 0.19 ACTA BOND $H L.S. 10 TEMP -103.00 WGHT 0.028100 FVAR 0.64049 MOLE 1 C1 1 0.325804 0.398493 0.349738 11.00000 0.02142 0.01877 = 0.02427 -0.00054 0.00123 -0.00028 C2 1 0.424717 0.351162 0.293603 11.00000 0.01779 0.02668 = 0.02115 0.00392 0.00344 0.00148 AFIX 13 H2 2 0.488951 0.413166 0.312838 11.00000 -1.20000 AFIX 0 C3 1 0.469530 0.220364 0.335143 11.00000 0.02317 0.02692 = 0.02506 0.00109 0.00853 0.00372 AFIX 23 H3A 2 0.418076 0.153195 0.299509 11.00000 -1.20000 H3B 2 0.546286 0.206781 0.313226 11.00000 -1.20000 AFIX 0 C4 1 0.572754 0.283020 0.509771 11.00000 0.01737 0.03113 = 0.03178 0.00453 0.00350 -0.00044 AFIX 23 H4A 2 0.558248 0.374659 0.492881 11.00000 -1.20000 H4B 2 0.644706 0.258520 0.482272 11.00000 -1.20000 AFIX 0 C5 1 0.586014 0.263452 0.632045 11.00000 0.02012 0.02983 = 0.02951 0.00275 -0.00085 0.00032 AFIX 23 H5A 2 0.605145 0.173144 0.650660 11.00000 -1.20000 H5B 2 0.647759 0.318720 0.669083 11.00000 -1.20000 AFIX 0 C6 1 0.468231 0.298080 0.782848 11.00000 0.03603 0.03428 = 0.02256 -0.00231 -0.00140 0.00433 AFIX 23 H6A 2 0.494483 0.380646 0.816825 11.00000 -1.20000 H6B 2 0.513565 0.227803 0.821330 11.00000 -1.20000 AFIX 0 C7 1 0.338991 0.278287 0.785026 11.00000 0.03621 0.03358 = 0.02012 -0.00175 0.00422 0.00332 AFIX 23 H7A 2 0.325339 0.198985 0.825171 11.00000 -1.20000 H7B 2 0.306404 0.351452 0.821294 11.00000 -1.20000 AFIX 0 C8 1 0.254860 0.399344 0.628439 11.00000 0.02391 0.02549 = 0.02565 -0.00503 0.00618 0.00485 AFIX 23 H8A 2 0.320217 0.457689 0.650133 11.00000 -1.20000 H8B 2 0.189065 0.430372 0.662980 11.00000 -1.20000 AFIX 0 C9 1 0.224112 0.401781 0.506373 11.00000 0.02388 0.02605 = 0.02649 -0.00230 0.00500 0.00689 AFIX 23 H9A 2 0.157173 0.345720 0.484465 11.00000 -1.20000 H9B 2 0.203150 0.489941 0.481959 11.00000 -1.20000 AFIX 0 C10 1 0.366731 0.228709 0.489835 11.00000 0.01836 0.01570 = 0.02022 -0.00048 0.00091 -0.00014 C11 1 0.382150 0.216972 0.615881 11.00000 0.01904 0.01922 = 0.02396 -0.00203 0.00412 0.00032 C12 1 0.395156 0.354176 0.169081 11.00000 0.02386 0.03959 = 0.02507 0.00290 0.00522 0.00209 AFIX 23 H12A 2 0.330459 0.295097 0.146907 11.00000 -1.20000 H12B 2 0.369721 0.441527 0.146113 11.00000 -1.20000 AFIX 0 C13 1 0.494656 0.316756 0.110059 11.00000 0.02618 0.04880 = 0.02526 0.00165 0.00560 0.00451 AFIX 23 H13A 2 0.513259 0.225284 0.123683 11.00000 -1.20000 H13B 2 0.473091 0.328751 0.030233 11.00000 -1.20000 AFIX 0 C14 1 0.280132 0.127987 0.437702 11.00000 0.02520 0.02817 = 0.02469 -0.00547 0.00594 -0.00541 AFIX 137 H14A 2 0.253467 0.151601 0.361526 11.00000 -1.50000 H14B 2 0.214708 0.124457 0.478710 11.00000 -1.50000 H14C 2 0.317234 0.043949 0.439766 11.00000 -1.50000 AFIX 0 C15 1 0.398040 0.074866 0.647285 11.00000 0.03367 0.02518 = 0.02347 0.00378 0.00815 0.00037 AFIX 137 H15A 2 0.433551 0.068020 0.723759 11.00000 -1.50000 H15B 2 0.447412 0.033841 0.599789 11.00000 -1.50000 H15C 2 0.323269 0.032292 0.638294 11.00000 -1.50000 AFIX 0 N1 3 0.321192 0.357751 0.454221 11.00000 0.01731 0.02032 = 0.02184 0.00199 0.00489 0.00328 N2 3 0.477676 0.206082 0.454046 11.00000 0.01689 0.02265 = 0.02012 0.00170 0.00421 0.00083 N3 3 0.477195 0.297347 0.665636 11.00000 0.01767 0.02701 = 0.01822 -0.00248 -0.00010 -0.00017 N4 3 0.285841 0.268679 0.668234 11.00000 0.02494 0.02442 = 0.01717 -0.00141 0.00519 0.00278 O1 4 0.257500 0.478166 0.305870 11.00000 0.03099 0.03241 = 0.02903 0.00830 0.00421 0.01211 O2 4 0.592313 0.393073 0.147456 11.00000 0.02689 0.04050 = 0.05676 0.00108 0.01733 0.00359 AFIX 147 H2O 2 0.651366 0.347205 0.153878 11.00000 -1.50000 HKLF 4 REM NC281-c at 170 K in P2(1)/n REM R1 = 0.0383 for 1598 Fo > 4sig(Fo) and 0.0896 for all 2854 data REM 193 parameters refined using 0 restraints END WGHT 0.0282 0.0000 REM Highest difference peak 0.156, deepest hole -0.162, 1-sigma level 0.036 Q1 1 0.3822 0.1591 0.6322 11.00000 0.05 0.16 Q2 1 0.4436 0.2278 0.6367 11.00000 0.05 0.15 Q3 1 0.3071 0.2212 0.6116 11.00000 0.05 0.15 Q4 1 0.3781 0.2410 0.5556 11.00000 0.05 0.15 Q5 1 0.3416 0.2997 0.4763 11.00000 0.05 0.14 Q6 1 0.2325 0.2080 0.6799 11.00000 0.05 0.14 Q7 1 0.3036 0.2684 0.7140 11.00000 0.05 0.13 Q8 1 0.4942 0.1315 0.5035 11.00000 0.05 0.13 Q9 1 0.2413 0.2907 0.6406 11.00000 0.05 0.12 Q10 1 0.4652 0.3096 0.3145 11.00000 0.05 0.12 Q11 1 0.6571 0.3864 0.6635 11.00000 0.05 0.12 Q12 1 0.3871 0.3583 0.3383 11.00000 0.05 0.12 Q13 1 0.5276 0.5225 0.4259 11.00000 0.05 0.12 Q14 1 0.5190 0.2815 0.6478 11.00000 0.05 0.12 Q15 1 0.3948 0.3244 0.2411 11.00000 0.05 0.11 Q16 1 0.3292 0.1999 0.4635 11.00000 0.05 0.11 Q17 1 0.4280 0.1262 0.2877 11.00000 0.05 0.11 Q18 1 0.3220 0.3240 0.8245 11.00000 0.05 0.11 Q19 1 0.3451 0.2002 0.2377 11.00000 0.05 0.11 Q20 1 0.2990 0.3320 0.4026 11.00000 0.05 0.11 Q21 1 0.2621 0.4757 0.2303 11.00000 0.05 0.11 Q22 1 0.2728 0.2834 0.8395 11.00000 0.05 0.11 Q23 1 0.2840 0.1158 0.7968 11.00000 0.05 0.11 Q24 1 0.0884 0.2681 0.4806 11.00000 0.05 0.10 Q25 1 0.3430 0.3611 0.2842 11.00000 0.05 0.10 ; _cod_data_source_file c5ra17133d2.cif _cod_data_source_block nc281-c _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 7222299 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 0.32580(15) 0.39849(16) 0.34974(14) 0.0217(4) Uani 1 1 d . C2 C 0.42472(14) 0.35116(16) 0.29360(13) 0.0218(4) Uani 1 1 d . H2 H 0.489 0.4132 0.3128 0.026 Uiso 1 1 calc R C3 C 0.46953(14) 0.22036(16) 0.33514(13) 0.0246(4) Uani 1 1 d . H3A H 0.4181 0.1532 0.2995 0.029 Uiso 1 1 calc R H3B H 0.5463 0.2068 0.3132 0.029 Uiso 1 1 calc R C4 C 0.57275(14) 0.28302(17) 0.50977(14) 0.0267(4) Uani 1 1 d . H4A H 0.5582 0.3747 0.4929 0.032 Uiso 1 1 calc R H4B H 0.6447 0.2585 0.4823 0.032 Uiso 1 1 calc R C5 C 0.58601(14) 0.26345(17) 0.63204(14) 0.0269(5) Uani 1 1 d . H5A H 0.6051 0.1731 0.6507 0.032 Uiso 1 1 calc R H5B H 0.6478 0.3187 0.6691 0.032 Uiso 1 1 calc R C6 C 0.46823(15) 0.29808(18) 0.78285(14) 0.0315(5) Uani 1 1 d . H6A H 0.4945 0.3806 0.8168 0.038 Uiso 1 1 calc R H6B H 0.5136 0.2278 0.8213 0.038 Uiso 1 1 calc R C7 C 0.33899(15) 0.27829(18) 0.78503(13) 0.0299(5) Uani 1 1 d . H7A H 0.3253 0.199 0.8252 0.036 Uiso 1 1 calc R H7B H 0.3064 0.3515 0.8213 0.036 Uiso 1 1 calc R C8 C 0.25486(15) 0.39934(16) 0.62844(13) 0.0248(4) Uani 1 1 d . H8A H 0.3202 0.4577 0.6501 0.03 Uiso 1 1 calc R H8B H 0.1891 0.4304 0.663 0.03 Uiso 1 1 calc R C9 C 0.22411(14) 0.40178(17) 0.50637(13) 0.0253(4) Uani 1 1 d . H9A H 0.1572 0.3457 0.4845 0.03 Uiso 1 1 calc R H9B H 0.2032 0.4899 0.482 0.03 Uiso 1 1 calc R C10 C 0.36673(13) 0.22871(15) 0.48984(13) 0.0183(4) Uani 1 1 d . C11 C 0.38215(14) 0.21697(16) 0.61588(13) 0.0206(4) Uani 1 1 d . C12 C 0.39516(15) 0.35418(18) 0.16908(13) 0.0293(5) Uani 1 1 d . H12A H 0.3305 0.2951 0.1469 0.035 Uiso 1 1 calc R H12B H 0.3697 0.4415 0.1461 0.035 Uiso 1 1 calc R C13 C 0.49466(15) 0.31676(18) 0.11006(14) 0.0332(5) Uani 1 1 d . H13A H 0.5133 0.2253 0.1237 0.04 Uiso 1 1 calc R H13B H 0.4731 0.3288 0.0302 0.04 Uiso 1 1 calc R C14 C 0.28013(14) 0.12799(15) 0.43770(13) 0.0258(5) Uani 1 1 d . H14A H 0.2535 0.1516 0.3615 0.039 Uiso 1 1 calc R H14B H 0.2147 0.1245 0.4787 0.039 Uiso 1 1 calc R H14C H 0.3172 0.0439 0.4398 0.039 Uiso 1 1 calc R C15 C 0.39804(15) 0.07487(16) 0.64729(14) 0.0270(5) Uani 1 1 d . H15A H 0.4336 0.068 0.7238 0.041 Uiso 1 1 calc R H15B H 0.4474 0.0338 0.5998 0.041 Uiso 1 1 calc R H15C H 0.3233 0.0323 0.6383 0.041 Uiso 1 1 calc R N1 N 0.32119(11) 0.35775(13) 0.45422(11) 0.0196(3) Uani 1 1 d . N2 N 0.47768(11) 0.20608(12) 0.45405(11) 0.0197(3) Uani 1 1 d . N3 N 0.47719(11) 0.29735(13) 0.66564(11) 0.0212(4) Uani 1 1 d . N4 N 0.28584(11) 0.26868(13) 0.66823(11) 0.0220(4) Uani 1 1 d . O1 O 0.25750(10) 0.47817(11) 0.30587(10) 0.0308(3) Uani 1 1 d . O2 O 0.59231(10) 0.39307(11) 0.14746(11) 0.0403(4) Uani 1 1 d . H2O H 0.6514 0.3472 0.1539 0.06 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 C1 0.0214(10) 0.0188(10) 0.0243(11) -0.0005(8) 0.0012(8) -0.0003(8) C2 0.0178(10) 0.0267(11) 0.0211(11) 0.0039(8) 0.0034(8) 0.0015(8) C3 0.0232(11) 0.0269(11) 0.0251(11) 0.0011(9) 0.0085(8) 0.0037(8) C4 0.0174(10) 0.0311(11) 0.0318(12) 0.0045(9) 0.0035(8) -0.0004(9) C5 0.0201(10) 0.0298(11) 0.0295(12) 0.0028(9) -0.0008(8) 0.0003(9) C6 0.0360(12) 0.0343(12) 0.0226(11) -0.0023(9) -0.0014(9) 0.0043(9) C7 0.0362(12) 0.0336(12) 0.0201(11) -0.0018(9) 0.0042(9) 0.0033(9) C8 0.0239(11) 0.0255(11) 0.0256(12) -0.0050(8) 0.0062(8) 0.0049(9) C9 0.0239(11) 0.0260(11) 0.0265(11) -0.0023(8) 0.0050(8) 0.0069(8) C10 0.0184(10) 0.0157(10) 0.0202(10) -0.0005(8) 0.0009(8) -0.0001(8) C11 0.0190(10) 0.0192(10) 0.0240(11) -0.0020(8) 0.0041(8) 0.0003(8) C12 0.0239(11) 0.0396(12) 0.0251(12) 0.0029(9) 0.0052(8) 0.0021(9) C13 0.0262(12) 0.0488(14) 0.0253(12) 0.0016(9) 0.0056(9) 0.0045(10) C14 0.0252(11) 0.0282(11) 0.0247(11) -0.0055(9) 0.0059(8) -0.0054(9) C15 0.0337(12) 0.0252(11) 0.0235(11) 0.0038(8) 0.0082(9) 0.0004(9) N1 0.0173(8) 0.0203(8) 0.0218(9) 0.0020(7) 0.0049(6) 0.0033(7) N2 0.0169(8) 0.0226(8) 0.0201(9) 0.0017(7) 0.0042(6) 0.0008(7) N3 0.0177(9) 0.0270(9) 0.0182(9) -0.0025(7) -0.0001(6) -0.0002(7) N4 0.0249(9) 0.0244(9) 0.0172(9) -0.0014(6) 0.0052(6) 0.0028(7) O1 0.0310(8) 0.0324(8) 0.0290(8) 0.0083(6) 0.0042(6) 0.0121(6) O2 0.0269(8) 0.0405(9) 0.0568(10) 0.0011(7) 0.0173(7) 0.0036(7) 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 1 0 1 0.03 -1 0 -1 0.02 1 0 -1 0.04 -1 0 1 0.04 0 -1 0 0.095 0 1 0 0.095 -4 1 17 0.03 8 1 1 0.03 9 4 13 0.035 1 -1 -3 0.055 -17 -1 2 0.03 -1 0 -8 0.025 -1 -2 -2 0.07 2 -1 1 0.06 1 -3 3 0.08 -3 -3 1 0.08 1 2 -1 0.085 -3 3 1 0.075 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 C1 N1 121.11(16) O1 C1 C2 121.13(16) N1 C1 C2 117.52(15) C1 C2 C12 111.65(14) C1 C2 C3 112.96(14) C12 C2 C3 112.06(15) C1 C2 H2 106.6 C12 C2 H2 106.6 C3 C2 H2 106.6 N2 C3 C2 113.49(14) 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 111.08(14) 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 106.27(13) N3 C5 H5A 110.5 C4 C5 H5A 110.5 N3 C5 H5B 110.5 C4 C5 H5B 110.5 H5A C5 H5B 108.7 N3 C6 C7 102.91(13) N3 C6 H6A 111.2 C7 C6 H6A 111.2 N3 C6 H6B 111.2 C7 C6 H6B 111.2 H6A C6 H6B 109.1 N4 C7 C6 106.02(13) N4 C7 H7A 110.5 C6 C7 H7A 110.5 N4 C7 H7B 110.5 C6 C7 H7B 110.5 H7A C7 H7B 108.7 N4 C8 C9 111.28(14) N4 C8 H8A 109.4 C9 C8 H8A 109.4 N4 C8 H8B 109.4 C9 C8 H8B 109.4 H8A C8 H8B 108 N1 C9 C8 109.95(14) N1 C9 H9A 109.7 C8 C9 H9A 109.7 N1 C9 H9B 109.7 C8 C9 H9B 109.7 H9A C9 H9B 108.2 N2 C10 N1 111.01(13) N2 C10 C14 109.46(13) N1 C10 C14 107.64(13) N2 C10 C11 107.86(13) N1 C10 C11 110.77(13) C14 C10 C11 110.11(14) N3 C11 N4 101.30(13) N3 C11 C15 112.85(14) N4 C11 C15 108.40(14) N3 C11 C10 110.63(13) N4 C11 C10 114.74(13) C15 C11 C10 108.84(13) C13 C12 C2 113.19(14) C13 C12 H12A 108.9 C2 C12 H12A 108.9 C13 C12 H12B 108.9 C2 C12 H12B 108.9 H12A C12 H12B 107.8 O2 C13 C12 110.18(15) O2 C13 H13A 109.6 C12 C13 H13A 109.6 O2 C13 H13B 109.6 C12 C13 H13B 109.6 H13A C13 H13B 108.1 C10 C14 H14A 109.5 C10 C14 H14B 109.5 H14A C14 H14B 109.5 C10 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 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 C1 N1 C9 116.93(13) C1 N1 C10 119.93(13) C9 N1 C10 115.20(13) C10 N2 C3 110.49(13) C10 N2 C4 115.35(13) C3 N2 C4 110.63(13) C5 N3 C6 118.20(13) C5 N3 C11 113.39(13) C6 N3 C11 105.11(12) C8 N4 C11 111.13(13) C8 N4 C7 108.02(13) C11 N4 C7 101.55(12) C13 O2 H2O 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.2304(19) C1 N1 1.3653(19) C1 C2 1.519(2) C2 C12 1.527(2) C2 C3 1.528(2) C2 H2 1 C3 N2 1.4638(19) C3 H3A 0.99 C3 H3B 0.99 C4 N2 1.470(2) C4 C5 1.508(2) C4 H4A 0.99 C4 H4B 0.99 C5 N3 1.4460(19) C5 H5A 0.99 C5 H5B 0.99 C6 N3 1.464(2) C6 C7 1.542(2) C6 H6A 0.99 C6 H6B 0.99 C7 N4 1.492(2) C7 H7A 0.99 C7 H7B 0.99 C8 N4 1.480(2) C8 C9 1.499(2) C8 H8A 0.99 C8 H8B 0.99 C9 N1 1.4628(19) C9 H9A 0.99 C9 H9B 0.99 C10 N2 1.4567(19) C10 N1 1.495(2) C10 C14 1.543(2) C10 C11 1.545(2) C11 N3 1.465(2) C11 N4 1.484(2) C11 C15 1.540(2) C12 C13 1.515(2) C12 H12A 0.99 C12 H12B 0.99 C13 O2 1.424(2) C13 H13A 0.99 C13 H13B 0.99 C14 H14A 0.98 C14 H14B 0.98 C14 H14C 0.98 C15 H15A 0.98 C15 H15B 0.98 C15 H15C 0.98 O2 H2O 0.84 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 N4 0.84 1.98 2.8228(18) 177.2 4_665