#------------------------------------------------------------------------------ #$Date: 2016-03-26 22:34:52 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180511 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/80/7218004.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_7218004 loop_ _publ_author_name 'Tumanova, Natalia' 'Tumanov, Nikolay' 'Robeyns, Koen' 'Filinchuk, Yaroslav' 'Wouters, Johan' 'Leyssens, Tom' _publ_section_title ; Structural insight into cocrystallization with zwitterionic co-formers: cocrystals of S-naproxen ; _journal_issue 35 _journal_name_full CrystEngComm _journal_page_first 8185 _journal_paper_doi 10.1039/C4CE00353E _journal_volume 16 _journal_year 2014 _chemical_absolute_configuration syn _chemical_formula_moiety 'C14 H14 O3, C3 H7 N O2' _chemical_formula_sum 'C17 H21 N O5' _chemical_formula_weight 319.35 _chemical_name_common 'S-naproxen L-alanine' _chemical_name_systematic ; (+)-(S)-2-(6-methoxynaphthalen-2-yl) propanoic acid (S)-2-Aminopropionic acid ; _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2013 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.05836(11) _cell_length_b 7.1121(3) _cell_length_c 45.2723(17) _cell_measurement_reflns_used 9136 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 32.3580 _cell_measurement_theta_min 2.5950 _cell_volume 1628.70(10) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies,Version 1.171.36.28 ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies,Version 1.171.36.28 ; _computing_molecular_graphics 'Mercury 3.1' _computing_publication_material enCIFer _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 5.814 _diffrn_measured_fraction_theta_full 0.969 _diffrn_measured_fraction_theta_max 0.833 _diffrn_measurement_device_type 'Pilatus 2M' _diffrn_measurement_method '720 images, \D\F 0.5\%' _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.68239 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_unetI/netI 0.0326 _diffrn_reflns_Laue_measured_fraction_full 0.969 _diffrn_reflns_Laue_measured_fraction_max 0.833 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 70 _diffrn_reflns_limit_l_min -70 _diffrn_reflns_number 14337 _diffrn_reflns_point_group_measured_fraction_full 0.973 _diffrn_reflns_point_group_measured_fraction_max 0.828 _diffrn_reflns_theta_full 24.169 _diffrn_reflns_theta_max 32.392 _diffrn_reflns_theta_min 1.728 _diffrn_source synchrotron _diffrn_source_type 'ESRF beamline SNBL BM01A' _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.82103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.411 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.066 _refine_ls_abs_structure_details ; Flack x determined using 2094 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.2(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 231 _refine_ls_number_reflns 5462 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.096 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0500 _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^)+(0.0736P)^2^+0.3919P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1338 _refine_ls_wR_factor_ref 0.1349 _reflns_Friedel_coverage 0.708 _reflns_Friedel_fraction_full 0.979 _reflns_Friedel_fraction_max 0.822 _reflns_number_gt 5314 _reflns_number_total 5462 _reflns_threshold_expression 'I > 2\s(I)' _cod_duplicate_entry 7215887 _cod_data_source_file c4ce00353e5.cif _cod_data_source_block S-naproxen_L-alanine _cod_original_cell_volume 1628.69(10) _cod_database_code 7218004 #BEGIN Tags that were not found in dictionaries: _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_min 0.987 _shelx_estimated_absorpt_t_max 0.998 _shelxl_version_number 2013-4 _shelx_res_file ; TITL NT_sc1_100K in P212121 #19 CELL 0.68239 5.058363 7.112081 45.272263 90 90 90 ZERR 4 0.000106 0.000295 0.00165 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N O DISP C 0.003 0.001 10.646 DISP H -0 0 0.622 DISP N 0.006 0.003 17.944 DISP O 0.011 0.006 29.475 UNIT 68 84 4 20 L.S. 10 0 0 PLAN 20 SIZE 0.15 0.13 0.02 TEMP -173 LIST 4 CONF BOND $H BOND fmap 2 53 acta OMIT 3 2 0 OMIT 6 2 0 OMIT 7 4 0 WGHT 0.073600 0.391900 FVAR 6.33645 0.02916 O1 4 0.674785 0.526235 0.166802 11.00000 0.02494 0.03066 = 0.02103 0.00080 0.00200 -0.01232 C1 1 0.855439 0.637497 0.162227 11.00000 0.01610 0.01568 = 0.01925 0.00135 0.00027 0.00085 O2 4 0.967253 0.740556 0.182571 11.00000 0.02903 0.02544 = 0.02197 -0.00607 0.00405 -0.00915 H2 2 0.899476 0.727679 0.202377 11.00000 0.05404 C2 1 1.063422 0.474699 0.119512 11.00000 0.02133 0.01850 = 0.02430 0.00033 0.00294 0.00379 AFIX 137 H2A 2 1.205595 0.425238 0.131996 11.00000 -1.50000 H2B 2 1.128239 0.489655 0.099248 11.00000 -1.50000 H2C 2 0.914052 0.386950 0.119657 11.00000 -1.50000 AFIX 0 O4 4 0.230675 0.233106 0.266183 11.00000 0.01538 0.02687 = 0.02004 0.00440 0.00040 0.00163 C4 1 0.768748 0.767216 0.112617 11.00000 0.01808 0.01501 = 0.01800 0.00099 0.00193 -0.00062 N1 3 0.415990 0.438008 0.220568 11.00000 0.01394 0.01386 = 0.01962 0.00025 0.00078 -0.00266 H1A 2 0.471672 0.460688 0.203208 11.00000 21.00000 H1B 2 0.540540 0.367984 0.231830 11.00000 21.00000 H1C 2 0.372585 0.539633 0.230267 11.00000 21.00000 C15 1 0.069868 0.250600 0.244944 11.00000 0.01309 0.01476 = 0.02290 0.00421 0.00106 0.00130 C17 1 0.275701 0.141197 0.197299 11.00000 0.04137 0.02094 = 0.02570 -0.00511 0.00506 -0.00712 AFIX 137 H17A 2 0.123706 0.059068 0.193597 11.00000 0.04658 H17B 2 0.410632 0.071744 0.208356 11.00000 0.05343 H17C 2 0.349777 0.183382 0.178427 11.00000 0.03822 AFIX 0 C16 1 0.186813 0.311763 0.215257 11.00000 0.01480 0.01549 = 0.01965 0.00255 -0.00058 -0.00494 AFIX 13 H16 2 0.049141 0.381829 0.203849 11.00000 -1.20000 AFIX 0 O3 4 -0.127887 1.067276 0.022997 11.00000 0.02267 0.02358 = 0.02483 0.00192 -0.00387 0.00281 C3 1 0.973220 0.666082 0.131462 11.00000 0.01788 0.01631 = 0.01729 0.00130 0.00192 -0.00080 AFIX 13 H3 2 1.131968 0.749030 0.133330 11.00000 -1.20000 AFIX 0 O5 4 -0.173517 0.218288 0.245754 11.00000 0.01286 0.02792 = 0.03420 0.01238 0.00058 -0.00239 C5 1 0.691979 0.952026 0.121064 11.00000 0.02225 0.01755 = 0.02183 -0.00276 -0.00190 0.00006 AFIX 43 H5 2 0.773210 1.008886 0.137742 11.00000 -1.20000 AFIX 0 C6 1 0.503413 1.049880 0.105673 11.00000 0.02525 0.01579 = 0.02350 -0.00292 -0.00239 0.00106 AFIX 43 H6 2 0.455581 1.172820 0.111899 11.00000 -1.20000 AFIX 0 C7 1 0.378157 0.969481 0.080438 11.00000 0.01895 0.01785 = 0.01889 0.00052 0.00088 -0.00130 C8 1 0.180636 1.068262 0.064319 11.00000 0.02041 0.01705 = 0.02261 0.00094 -0.00019 0.00119 AFIX 43 H8 2 0.128984 1.191035 0.070238 11.00000 -1.20000 AFIX 0 C10 1 -0.209181 1.251633 0.031441 11.00000 0.02673 0.02429 = 0.02938 0.00364 -0.00307 0.00503 AFIX 137 H10A 2 -0.347482 1.295767 0.017960 11.00000 0.02841 H10B 2 -0.057503 1.337157 0.030511 11.00000 0.02927 H10C 2 -0.278413 1.248642 0.051653 11.00000 0.02151 AFIX 0 C9 1 0.064576 0.985010 0.040077 11.00000 0.01818 0.02173 = 0.02046 0.00311 -0.00031 -0.00071 C11 1 0.142032 0.802553 0.030926 11.00000 0.02375 0.02330 = 0.02079 -0.00090 -0.00176 -0.00045 AFIX 43 H11 2 0.061207 0.746652 0.014143 11.00000 -1.20000 AFIX 0 C12 1 0.333061 0.706435 0.046191 11.00000 0.02187 0.01805 = 0.02157 -0.00258 -0.00091 0.00034 AFIX 43 H12 2 0.383934 0.584507 0.039777 11.00000 -1.20000 AFIX 0 C13 1 0.456578 0.786522 0.071534 11.00000 0.01906 0.01803 = 0.01755 0.00009 0.00096 -0.00056 C14 1 0.651247 0.688123 0.088093 11.00000 0.01990 0.01444 = 0.01964 -0.00071 0.00135 -0.00068 AFIX 43 H14 2 0.701516 0.565140 0.082133 11.00000 -1.20000 AFIX 0 HKLF 4 REM NT_sc1_100K in P212121 #19 REM R1 = 0.0500 for 5314 Fo > 4sig(Fo) and 0.0512 for all 5462 data REM 231 parameters refined using 0 restraints END WGHT 0.0736 0.4018 REM Highest difference peak 0.411, deepest hole -0.280, 1-sigma level 0.066 Q1 1 0.3716 0.7418 0.0601 11.00000 0.05 0.41 Q2 1 0.7317 0.7332 0.1005 11.00000 0.05 0.39 Q3 1 0.5427 0.7381 0.0787 11.00000 0.05 0.35 Q4 1 0.2180 0.7581 0.0392 11.00000 0.05 0.32 Q5 1 0.2488 0.2418 0.2779 11.00000 0.05 0.32 Q6 1 0.0986 0.2278 0.2624 11.00000 0.05 0.32 Q7 1 0.3909 0.9799 0.0996 11.00000 0.05 0.31 Q8 1 0.0838 0.9961 0.0591 11.00000 0.05 0.31 Q9 1 -0.0701 1.0555 0.0391 11.00000 0.05 0.31 Q10 1 0.8418 0.6978 0.1185 11.00000 0.05 0.31 Q11 1 0.6651 0.4952 0.1799 11.00000 0.05 0.30 Q12 1 0.2400 1.0242 0.0796 11.00000 0.05 0.30 Q13 1 0.5776 1.0002 0.1189 11.00000 0.05 0.27 Q14 1 -0.1712 0.2180 0.2570 11.00000 0.05 0.27 Q15 1 0.1721 1.0549 0.0431 11.00000 0.05 0.24 Q16 1 0.8714 0.6674 0.1805 11.00000 0.05 0.23 Q17 1 0.6655 0.9941 0.1030 11.00000 0.05 0.23 Q18 1 0.2333 0.2515 0.1985 11.00000 0.05 0.22 Q19 1 0.8891 0.6337 0.1398 11.00000 0.05 0.21 Q20 1 0.3015 0.3814 0.2202 11.00000 0.05 0.21 ; _shelx_res_checksum 62789 #END Tags that were not found in dictionaries loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -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 O1 O 0.6748(3) 0.5262(2) 0.16680(3) 0.0255(3) Uani 1 1 d . . C1 C 0.8554(3) 0.6375(3) 0.16223(4) 0.0170(3) Uani 1 1 d . . O2 O 0.9673(3) 0.7406(2) 0.18257(3) 0.0255(3) Uani 1 1 d . . H2 H 0.899(8) 0.728(5) 0.2024(8) 0.054(10) Uiso 1 1 d . . C2 C 1.0634(4) 0.4747(3) 0.11951(4) 0.0214(4) Uani 1 1 d . . H2A H 1.2056 0.4252 0.1320 0.032 Uiso 1 1 calc R U H2B H 1.1282 0.4897 0.0992 0.032 Uiso 1 1 calc R U H2C H 0.9141 0.3870 0.1197 0.032 Uiso 1 1 calc R U O4 O 0.2307(2) 0.2331(2) 0.26618(3) 0.0208(3) Uani 1 1 d . . C4 C 0.7687(3) 0.7672(3) 0.11262(4) 0.0170(3) Uani 1 1 d . . N1 N 0.4160(3) 0.4380(2) 0.22057(3) 0.0158(3) Uani 1 1 d . . H1A H 0.472(6) 0.461(4) 0.2032(7) 0.029(4) Uiso 1 1 d . U H1B H 0.541(6) 0.368(4) 0.2318(7) 0.029(4) Uiso 1 1 d . U H1C H 0.373(6) 0.540(5) 0.2303(7) 0.029(4) Uiso 1 1 d . U C15 C 0.0699(3) 0.2506(3) 0.24494(4) 0.0169(3) Uani 1 1 d . . C17 C 0.2757(5) 0.1412(4) 0.19730(5) 0.0293(5) Uani 1 1 d . . H17A H 0.1237 0.0591 0.1936 0.047(9) Uiso 1 1 calc R . H17B H 0.4106 0.0717 0.2084 0.053(11) Uiso 1 1 calc R . H17C H 0.3498 0.1834 0.1784 0.038(8) Uiso 1 1 calc R . C16 C 0.1868(3) 0.3118(3) 0.21526(4) 0.0166(3) Uani 1 1 d . . H16 H 0.0491 0.3818 0.2038 0.020 Uiso 1 1 calc R U O3 O -0.1279(3) 1.0673(2) 0.02300(3) 0.0237(3) Uani 1 1 d . . C3 C 0.9732(3) 0.6661(3) 0.13146(4) 0.0172(3) Uani 1 1 d . . H3 H 1.1320 0.7490 0.1333 0.021 Uiso 1 1 calc R U O5 O -0.1735(3) 0.2183(2) 0.24575(3) 0.0250(3) Uani 1 1 d . . C5 C 0.6920(4) 0.9520(3) 0.12106(4) 0.0205(4) Uani 1 1 d . . H5 H 0.7732 1.0089 0.1377 0.025 Uiso 1 1 calc R U C6 C 0.5034(4) 1.0499(3) 0.10567(4) 0.0215(4) Uani 1 1 d . . H6 H 0.4556 1.1728 0.1119 0.026 Uiso 1 1 calc R U C7 C 0.3782(4) 0.9695(3) 0.08044(4) 0.0186(4) Uani 1 1 d . . C8 C 0.1806(4) 1.0683(3) 0.06432(4) 0.0200(4) Uani 1 1 d . . H8 H 0.1290 1.1910 0.0702 0.024 Uiso 1 1 calc R U C10 C -0.2092(4) 1.2516(3) 0.03144(5) 0.0268(4) Uani 1 1 d . . H10A H -0.3475 1.2958 0.0180 0.028(7) Uiso 1 1 calc R . H10B H -0.0575 1.3372 0.0305 0.029(7) Uiso 1 1 calc R . H10C H -0.2784 1.2486 0.0517 0.022(6) Uiso 1 1 calc R . C9 C 0.0646(4) 0.9850(3) 0.04008(4) 0.0201(4) Uani 1 1 d . . C11 C 0.1420(4) 0.8026(3) 0.03093(4) 0.0226(4) Uani 1 1 d . . H11 H 0.0612 0.7467 0.0141 0.027 Uiso 1 1 calc R U C12 C 0.3331(4) 0.7064(3) 0.04619(4) 0.0205(4) Uani 1 1 d . . H12 H 0.3839 0.5845 0.0398 0.025 Uiso 1 1 calc R U C13 C 0.4566(4) 0.7865(3) 0.07153(4) 0.0182(3) Uani 1 1 d . . C14 C 0.6512(4) 0.6881(3) 0.08809(4) 0.0180(3) Uani 1 1 d . . H14 H 0.7015 0.5651 0.0821 0.022 Uiso 1 1 calc R 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 O1 0.0249(6) 0.0307(9) 0.0210(6) 0.0008(6) 0.0020(5) -0.0123(6) C1 0.0161(7) 0.0157(10) 0.0192(7) 0.0013(6) 0.0003(5) 0.0008(6) O2 0.0290(7) 0.0254(9) 0.0220(6) -0.0061(5) 0.0041(5) -0.0091(6) C2 0.0213(7) 0.0185(11) 0.0243(7) 0.0003(7) 0.0029(6) 0.0038(7) O4 0.0154(5) 0.0269(9) 0.0200(5) 0.0044(5) 0.0004(4) 0.0016(5) C4 0.0181(6) 0.0150(10) 0.0180(6) 0.0010(6) 0.0019(5) -0.0006(6) N1 0.0139(5) 0.0139(9) 0.0196(6) 0.0003(5) 0.0008(5) -0.0027(5) C15 0.0131(6) 0.0148(10) 0.0229(7) 0.0042(6) 0.0011(5) 0.0013(6) C17 0.0414(12) 0.0209(13) 0.0257(8) -0.0051(7) 0.0051(8) -0.0071(9) C16 0.0148(6) 0.0155(10) 0.0197(6) 0.0026(6) -0.0006(5) -0.0049(6) O3 0.0227(6) 0.0236(9) 0.0248(6) 0.0019(5) -0.0039(5) 0.0028(6) C3 0.0179(7) 0.0163(10) 0.0173(6) 0.0013(6) 0.0019(5) -0.0008(6) O5 0.0129(5) 0.0279(9) 0.0342(7) 0.0124(6) 0.0006(5) -0.0024(6) C5 0.0222(7) 0.0175(11) 0.0218(7) -0.0028(6) -0.0019(6) 0.0001(7) C6 0.0253(8) 0.0158(11) 0.0235(7) -0.0029(7) -0.0024(6) 0.0011(7) C7 0.0189(7) 0.0179(10) 0.0189(6) 0.0005(6) 0.0009(5) -0.0013(6) C8 0.0204(7) 0.0171(11) 0.0226(7) 0.0009(6) -0.0002(6) 0.0012(7) C10 0.0267(9) 0.0243(12) 0.0294(8) 0.0036(8) -0.0031(7) 0.0050(8) C9 0.0182(7) 0.0217(11) 0.0205(7) 0.0031(6) -0.0003(5) -0.0007(7) C11 0.0238(8) 0.0233(12) 0.0208(7) -0.0009(7) -0.0018(6) -0.0004(7) C12 0.0219(7) 0.0181(11) 0.0216(7) -0.0026(6) -0.0009(6) 0.0003(7) C13 0.0191(7) 0.0180(10) 0.0176(6) 0.0001(6) 0.0010(5) -0.0006(6) C14 0.0199(7) 0.0144(10) 0.0196(6) -0.0007(6) 0.0013(5) -0.0007(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 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 O1 C1 O2 124.45(16) O1 C1 C3 122.02(17) O2 C1 C3 113.53(16) C1 O2 H2 117(2) C3 C2 H2A 109.5 C3 C2 H2B 109.5 H2A C2 H2B 109.5 C3 C2 H2C 109.5 H2A C2 H2C 109.5 H2B C2 H2C 109.5 C14 C4 C5 118.39(17) C14 C4 C3 123.47(18) C5 C4 C3 118.13(16) C16 N1 H1A 103(2) C16 N1 H1B 106.7(19) H1A N1 H1B 112(3) C16 N1 H1C 113(2) H1A N1 H1C 113(3) H1B N1 H1C 109(3) O5 C15 O4 126.25(17) O5 C15 C16 117.21(15) O4 C15 C16 116.51(14) C16 C17 H17A 109.5 C16 C17 H17B 109.5 H17A C17 H17B 109.5 C16 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 N1 C16 C17 109.65(16) N1 C16 C15 109.33(14) C17 C16 C15 110.80(17) N1 C16 H16 109.0 C17 C16 H16 109.0 C15 C16 H16 109.0 C9 O3 C10 116.42(16) C4 C3 C1 107.99(14) C4 C3 C2 115.08(15) C1 C3 C2 108.62(16) C4 C3 H3 108.3 C1 C3 H3 108.3 C2 C3 H3 108.3 C6 C5 C4 121.48(17) C6 C5 H5 119.3 C4 C5 H5 119.3 C5 C6 C7 120.8(2) C5 C6 H6 119.6 C7 C6 H6 119.6 C13 C7 C8 120.23(16) C13 C7 C6 118.11(17) C8 C7 C6 121.66(19) C9 C8 C7 119.70(19) C9 C8 H8 120.2 C7 C8 H8 120.2 O3 C10 H10A 109.5 O3 C10 H10B 109.5 H10A C10 H10B 109.5 O3 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 O3 C9 C8 124.54(19) O3 C9 C11 114.91(16) C8 C9 C11 120.55(17) C12 C11 C9 120.27(17) C12 C11 H11 119.9 C9 C11 H11 119.9 C11 C12 C13 121.04(19) C11 C12 H12 119.5 C13 C12 H12 119.5 C7 C13 C14 119.69(16) C7 C13 C12 118.21(17) C14 C13 C12 122.10(18) C4 C14 C13 121.48(18) C4 C14 H14 119.3 C13 C14 H14 119.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.226(2) C1 O2 1.306(2) C1 C3 1.528(2) O2 H2 0.96(4) C2 C3 1.534(3) C2 H2A 0.9800 C2 H2B 0.9800 C2 H2C 0.9800 O4 C15 1.266(2) C4 C14 1.379(2) C4 C5 1.423(3) C4 C3 1.522(3) N1 C16 1.486(2) N1 H1A 0.85(3) N1 H1B 0.95(3) N1 H1C 0.87(3) C15 O5 1.253(2) C15 C16 1.532(2) C17 C16 1.528(3) C17 H17A 0.9800 C17 H17B 0.9800 C17 H17C 0.9800 C16 H16 1.0000 O3 C9 1.374(2) O3 C10 1.426(3) C3 H3 1.0000 C5 C6 1.371(3) C5 H5 0.9500 C6 C7 1.426(3) C6 H6 0.9500 C7 C13 1.419(3) C7 C8 1.423(3) C8 C9 1.378(3) C8 H8 0.9500 C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 C9 C11 1.417(3) C11 C12 1.371(3) C11 H11 0.9500 C12 C13 1.425(2) C12 H12 0.9500 C13 C14 1.422(3) C14 H14 0.9500 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1A O1 1_555 0.85(3) 2.00(3) 2.834(2) 168(3) N1 H1B O5 1_655 0.95(3) 1.90(3) 2.838(2) 167(3) N1 H1C O4 4_655 0.88(3) 2.44(3) 2.8211(19) 107(2) N1 H1C O5 4_555 0.88(3) 1.95(3) 2.794(2) 161(3) O2 H2 O4 4_655 0.97(4) 1.57(4) 2.5277(19) 172(4) 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 O5 C15 C16 N1 149.27(19) O4 C15 C16 N1 -32.4(2) O5 C15 C16 C17 -89.8(2) O4 C15 C16 C17 88.5(2) C14 C4 C3 C1 -115.45(19) C5 C4 C3 C1 63.5(2) C14 C4 C3 C2 6.1(2) C5 C4 C3 C2 -174.98(16) O1 C1 C3 C4 70.4(2) O2 C1 C3 C4 -110.21(19) O1 C1 C3 C2 -55.0(2) O2 C1 C3 C2 124.36(18) C14 C4 C5 C6 0.9(3) C3 C4 C5 C6 -178.11(17) C4 C5 C6 C7 -0.3(3) C5 C6 C7 C13 -0.8(3) C5 C6 C7 C8 179.51(18) C13 C7 C8 C9 0.3(3) C6 C7 C8 C9 -179.92(18) C10 O3 C9 C8 0.0(3) C10 O3 C9 C11 -179.53(17) C7 C8 C9 O3 179.88(17) C7 C8 C9 C11 -0.6(3) O3 C9 C11 C12 179.83(18) C8 C9 C11 C12 0.2(3) C9 C11 C12 C13 0.3(3) C8 C7 C13 C14 -179.03(17) C6 C7 C13 C14 1.2(3) C8 C7 C13 C12 0.2(3) C6 C7 C13 C12 -179.55(18) C11 C12 C13 C7 -0.5(3) C11 C12 C13 C14 178.68(18) C5 C4 C14 C13 -0.4(3) C3 C4 C14 C13 178.56(16) C7 C13 C14 C4 -0.7(3) C12 C13 C14 C4 -179.86(17)