#------------------------------------------------------------------------------ #$Date: 2018-01-11 04:50:34 +0200 (Thu, 11 Jan 2018) $ #$Revision: 205058 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229941.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_7229941 loop_ _publ_author_name 'Nisar, Madiha' 'Sung, Herman H-Y.' 'Puschmann, Horst' 'Lakerveld, Richard' 'Haynes, Richard' 'Williams, Ian Duncan' _publ_section_title ; 11-Azaartemisinin cocrystals with preserved lactam: acid heterosynthons ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C7CE01875D _journal_year 2018 _chemical_absolute_configuration ad _chemical_formula_moiety 'C15 H23 N O4, C7 H6 O3' _chemical_formula_sum 'C22 H29 N O7' _chemical_formula_weight 419.46 _chemical_name_common 11-Aza:Sal _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2017-07-17 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2017-08-15 deposited with the CCDC. 2018-01-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.3070(12) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.79451(14) _cell_length_b 9.30687(13) _cell_length_c 11.51291(16) _cell_measurement_reflns_used 6402 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 75.2640 _cell_measurement_theta_min 3.8220 _cell_volume 1048.62(3) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3577 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -35.00 36.00 1.00 1.00 -- 40.45 -37.00 0.00 71 2 \w 15.00 68.00 1.00 1.00 -- 40.45 37.00-120.00 53 3 \w 29.00 92.00 1.00 1.00 -- 40.45 57.00 -90.00 63 4 \w 145.00 176.00 1.00 2.00 -- 110.57 125.00 -90.00 31 5 \w 121.00 148.00 1.00 2.00 -- 110.57 45.00-180.00 27 6 \w 95.00 140.00 1.00 2.00 -- 110.57 125.00 -90.00 45 7 \w 83.00 112.00 1.00 2.00 -- 110.57 45.00-180.00 29 8 \w 85.00 119.00 1.00 2.00 -- 110.57 30.00-150.00 34 9 \w 86.00 173.00 1.00 2.00 -- 110.57 30.00 -90.00 87 10 \w 132.00 159.00 1.00 2.00 -- 110.57 61.00 90.00 27 11 \w 121.00 174.00 1.00 2.00 -- 110.57 77.00 120.00 53 12 \w 112.00 174.00 1.00 2.00 -- 110.57 77.00 90.00 62 13 \w 87.00 116.00 1.00 1.00 -- 40.45 37.00 150.00 29 14 \w 78.00 104.00 1.00 2.00 -- 110.57 77.00 60.00 26 15 \w 77.00 104.00 1.00 2.00 -- 110.57 77.00 90.00 27 16 \w 77.00 104.00 1.00 2.00 -- 110.57 77.00 120.00 27 17 \w 84.00 109.00 1.00 2.00 -- 110.57 45.00 150.00 25 18 \w 83.00 109.00 1.00 2.00 -- 110.57 45.00 120.00 26 19 \w 82.00 110.00 1.00 2.00 -- 110.57 61.00 150.00 28 20 \w 86.00 117.00 1.00 2.00 -- 110.57 30.00 120.00 31 21 \w 81.00 107.00 1.00 2.00 -- 110.57 61.00 60.00 26 22 \w 80.00 106.00 1.00 2.00 -- 110.57 61.00 90.00 26 23 \w 80.00 107.00 1.00 2.00 -- 110.57 61.00 120.00 27 24 \w 77.00 104.00 1.00 2.00 -- 110.57 77.00 150.00 27 25 \w 19.00 79.00 1.00 1.00 -- 40.45 37.00 150.00 60 26 \w 28.00 106.00 1.00 2.00 -- 110.57 -94.00 30.00 78 27 \w 37.00 109.00 1.00 2.00 -- 110.57-125.00 -90.00 72 28 \w 12.00 56.00 1.00 1.00 -- 40.45 57.00-150.00 44 29 \w 77.00 160.00 1.00 2.00 -- 110.57 77.00-180.00 83 30 \w 80.00 107.00 1.00 2.00 -- 110.57 61.00-180.00 27 31 \w -61.00 21.00 1.00 1.00 -- -40.45 37.00 30.00 82 32 \w -67.00 28.00 1.00 1.00 -- -40.45 57.00 120.00 95 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0349412000 _diffrn_orient_matrix_UB_12 0.0492318000 _diffrn_orient_matrix_UB_13 -0.1229416000 _diffrn_orient_matrix_UB_21 0.1497918000 _diffrn_orient_matrix_UB_22 -0.0454822000 _diffrn_orient_matrix_UB_23 0.0238388000 _diffrn_orient_matrix_UB_31 -0.0336577000 _diffrn_orient_matrix_UB_32 -0.1514253000 _diffrn_orient_matrix_UB_33 -0.0472241000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_unetI/netI 0.0283 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 8079 _diffrn_reflns_point_group_measured_fraction_full 0.962 _diffrn_reflns_point_group_measured_fraction_max 0.962 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 66.996 _diffrn_reflns_theta_min 3.843 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 0.80 _diffrn_source_power 0.040 _diffrn_source_target Cu _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 0.820 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.40396 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.158 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.034 _refine_ls_abs_structure_details ; Flack x determined using 1534 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.06(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 286 _refine_ls_number_reflns 3602 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.004 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0273 _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^)+(0.0400P)^2^+0.1300P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.0680 _reflns_Friedel_coverage 0.813 _reflns_Friedel_fraction_full 0.925 _reflns_Friedel_fraction_max 0.926 _reflns_number_gt 3518 _reflns_number_total 3602 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce01875d2.cif _cod_data_source_block cpd3_madiha26cult _cod_database_code 7229941 _shelx_shelxl_version_number 2014/7 _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. ; _reflns_odcompleteness_completeness 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12) 2.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B) 2.c Aromatic/amide H refined with riding coordinates: C23(H23), C24(H24), C25(H25), C26(H26) 2.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C) ; _shelx_res_file ; madiha26cult.res created by SHELXL-2014/7 TITL madiha26CuLT in P21 #4 REM reset to P21 #4 CELL 1.54184 9.79451 9.30687 11.51291 90 92.307 90 ZERR 2 0.00014 0.00013 0.00016 0 0.0012 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O UNIT 44 58 2 14 L.S. 8 PLAN 20 TEMP -173 HTAB N11 O20 HTAB O21 O10 HTAB O22 O20 CONF BOND fmap 2 acta 133 OMIT 0 134 OMIT -9 -4 4 OMIT -2 0 6 OMIT -5 9 3 OMIT -9 0 5 OMIT -4 -10 3 OMIT -3 0 1 OMIT -6 9 4 OMIT -1 2 6 OMIT -8 1 6 OMIT -4 -3 5 OMIT -10 0 6 OMIT -5 9 2 OMIT 3 -10 4 OMIT -9 0 6 OMIT -3 3 3 OMIT -6 1 3 OMIT 5 6 6 OMIT 0 -3 1 OMIT -7 8 4 OMIT -8 -1 6 OMIT -4 10 1 OMIT -4 3 5 OMIT 5 -6 6 OMIT 2 -5 8 OMIT -8 -2 5 OMIT -3 -3 3 OMIT -9 -2 4 OMIT -8 2 5 REM REM REM WGHT 0.040000 0.130000 FVAR 9.13420 O1 4 0.444061 0.879910 0.342349 11.00000 0.01572 0.01143 = 0.02495 0.00208 -0.00076 -0.00013 O2 4 0.589437 0.892862 0.380226 11.00000 0.01534 0.01566 = 0.02545 -0.00358 0.00095 -0.00172 O3 4 0.628829 0.648947 0.392906 11.00000 0.01577 0.01500 = 0.02022 -0.00004 0.00115 0.00191 O10 4 0.398969 0.778317 0.712644 11.00000 0.02234 0.02449 = 0.01684 -0.00176 -0.00043 0.00550 N11 3 0.494690 0.694622 0.551642 11.00000 0.01450 0.01557 = 0.01722 0.00085 -0.00144 0.00267 H11 2 0.567637 0.668153 0.594801 11.00000 0.03543 C1 1 0.393654 0.733105 0.354687 11.00000 0.01829 0.00837 = 0.01727 0.00125 -0.00151 -0.00031 C2 1 0.493970 0.646261 0.431540 11.00000 0.01531 0.01321 = 0.01603 0.00004 -0.00094 0.00104 AFIX 13 H2 2 0.462542 0.544025 0.429895 11.00000 -1.20000 AFIX 0 C3 1 0.661447 0.777249 0.330614 11.00000 0.01812 0.01343 = 0.02406 -0.00260 0.00470 0.00073 C4 1 0.624978 0.761036 0.200550 11.00000 0.02462 0.02059 = 0.02049 0.00027 0.00556 -0.00097 AFIX 23 H4A 2 0.593606 0.855161 0.169584 11.00000 -1.20000 H4B 2 0.708478 0.734253 0.159963 11.00000 -1.20000 AFIX 0 C5 1 0.514458 0.649043 0.172790 11.00000 0.02539 0.01650 = 0.01625 -0.00090 -0.00029 0.00086 AFIX 23 H5A 2 0.551564 0.553447 0.194733 11.00000 -1.20000 H5B 2 0.496173 0.648368 0.087591 11.00000 -1.20000 AFIX 0 C6 1 0.296780 0.526243 0.230500 11.00000 0.02266 0.01592 = 0.02099 -0.00190 -0.00497 0.00020 AFIX 13 H6 2 0.353093 0.453215 0.274477 11.00000 -1.20000 AFIX 0 C7 1 0.162269 0.543061 0.291101 11.00000 0.02034 0.01927 = 0.02832 -0.00240 -0.00459 -0.00256 AFIX 23 H7A 2 0.117053 0.448160 0.295175 11.00000 -1.20000 H7B 2 0.101368 0.607603 0.244383 11.00000 -1.20000 AFIX 0 C8 1 0.181638 0.604076 0.413899 11.00000 0.01713 0.01821 = 0.02422 0.00042 -0.00026 -0.00226 AFIX 23 H8A 2 0.235094 0.535420 0.463155 11.00000 -1.20000 H8B 2 0.091315 0.616831 0.448129 11.00000 -1.20000 AFIX 0 C9 1 0.275563 0.821918 0.531816 11.00000 0.01590 0.01478 = 0.01906 0.00026 -0.00020 0.00144 AFIX 13 H9 2 0.301395 0.923667 0.515474 11.00000 -1.20000 AFIX 0 C10 1 0.393322 0.759999 0.605229 11.00000 0.01623 0.01311 = 0.01879 0.00036 0.00101 -0.00123 C11 1 0.377338 0.668220 0.231543 11.00000 0.01989 0.01619 = 0.01683 0.00039 -0.00271 0.00207 AFIX 13 H11A 2 0.322381 0.738187 0.183154 11.00000 -1.20000 AFIX 0 C12 1 0.256244 0.748973 0.412261 11.00000 0.01590 0.01279 = 0.01840 0.00126 -0.00218 0.00154 AFIX 13 H12 2 0.199007 0.815033 0.362078 11.00000 -1.20000 AFIX 0 C13 1 0.810694 0.808272 0.358371 11.00000 0.02026 0.02510 = 0.03183 -0.00746 0.00480 -0.00291 AFIX 137 H13A 2 0.824964 0.822943 0.442274 11.00000 -1.50000 H13B 2 0.837793 0.895105 0.317014 11.00000 -1.50000 H13C 2 0.866091 0.726884 0.333820 11.00000 -1.50000 AFIX 0 C14 1 0.271088 0.470348 0.106736 11.00000 0.02904 0.02050 = 0.02535 -0.00331 -0.00757 -0.00027 AFIX 137 H14A 2 0.222653 0.543679 0.059949 11.00000 -1.50000 H14B 2 0.215507 0.382882 0.108580 11.00000 -1.50000 H14C 2 0.358629 0.448641 0.072313 11.00000 -1.50000 AFIX 0 C15 1 0.145399 0.830156 0.600260 11.00000 0.01849 0.03414 = 0.02428 -0.00336 0.00087 0.00420 AFIX 137 H15A 2 0.070480 0.867427 0.549922 11.00000 -1.50000 H15B 2 0.160412 0.894336 0.667040 11.00000 -1.50000 H15C 2 0.121792 0.733991 0.627733 11.00000 -1.50000 AFIX 0 O20 4 0.719246 0.659402 0.722667 11.00000 0.02211 0.01868 = 0.02083 0.00102 -0.00216 -0.00029 O21 4 0.554379 0.630494 0.849444 11.00000 0.02044 0.02533 = 0.02109 -0.00081 0.00006 0.00566 H21 2 0.501966 0.685670 0.793915 11.00000 0.05032 O22 4 0.953949 0.539823 0.761824 11.00000 0.01880 0.02995 = 0.02549 0.00607 0.00157 0.00123 H22 2 0.891479 0.588667 0.729772 11.00000 0.03573 C20 1 0.676884 0.606157 0.813225 11.00000 0.02107 0.01481 = 0.01859 -0.00679 -0.00330 -0.00049 C21 1 0.763309 0.510459 0.887148 11.00000 0.02067 0.01497 = 0.01827 -0.00530 -0.00316 -0.00114 C22 1 0.897504 0.480281 0.856024 11.00000 0.02131 0.01836 = 0.01847 -0.00271 -0.00176 -0.00272 C23 1 0.977537 0.385325 0.923740 11.00000 0.01844 0.02743 = 0.02575 -0.00166 -0.00272 0.00237 AFIX 43 H23 2 1.068312 0.364367 0.903022 11.00000 -1.20000 AFIX 0 C24 1 0.924830 0.321918 1.020734 11.00000 0.02727 0.02547 = 0.02454 0.00247 -0.00788 0.00363 AFIX 43 H24 2 0.980024 0.257740 1.066397 11.00000 -1.20000 AFIX 0 C25 1 0.791605 0.350841 1.052577 11.00000 0.03036 0.02514 = 0.01698 -0.00010 -0.00144 -0.00085 AFIX 43 H25 2 0.756036 0.306955 1.119448 11.00000 -1.20000 AFIX 0 C26 1 0.712270 0.444126 0.985515 11.00000 0.02192 0.02218 = 0.01829 -0.00501 -0.00012 0.00140 AFIX 43 H26 2 0.621318 0.463673 1.006519 11.00000 -1.20000 AFIX 0 HKLF 4 REM madiha26CuLT in P21 #4 REM R1 = 0.0273 for 3518 Fo > 4sig(Fo) and 0.0280 for all 3602 data REM 286 parameters refined using 1 restraints END WGHT 0.0419 0.0893 REM Highest difference peak 0.158, deepest hole -0.175, 1-sigma level 0.034 Q1 1 0.3225 0.7396 0.3870 11.00000 0.05 0.16 Q2 1 0.4391 0.6855 0.3978 11.00000 0.05 0.15 Q3 1 0.4390 0.6638 0.2002 11.00000 0.05 0.14 Q4 1 0.3834 0.6884 0.2976 11.00000 0.05 0.14 Q5 1 0.2612 0.7793 0.4740 11.00000 0.05 0.13 Q6 1 0.3393 0.7968 0.5604 11.00000 0.05 0.11 Q7 1 0.2263 0.6759 0.4129 11.00000 0.05 0.11 Q8 1 0.6008 0.6803 0.9669 11.00000 0.05 0.10 Q9 1 0.7409 0.7944 0.3479 11.00000 0.05 0.10 Q10 1 0.6451 0.7578 0.2591 11.00000 0.05 0.10 Q11 1 0.2340 0.5337 0.2641 11.00000 0.05 0.10 Q12 1 0.9121 0.7126 0.6365 11.00000 0.05 0.10 Q13 1 0.2855 0.4994 0.1699 11.00000 0.05 0.10 Q14 1 0.8403 0.6944 0.3414 11.00000 0.05 0.10 Q15 1 0.6433 0.8322 0.5049 11.00000 0.05 0.10 Q16 1 0.0776 0.5622 0.6430 11.00000 0.05 0.09 Q17 1 0.1682 0.5610 0.3554 11.00000 0.05 0.09 Q18 1 0.5068 0.3685 0.1137 11.00000 0.05 0.09 Q19 1 0.0646 0.2803 0.2224 11.00000 0.05 0.09 Q20 1 0.6976 0.2217 0.9834 11.00000 0.05 0.09 ; _shelx_res_checksum 62364 _olex2_date_sample_data_collection 2017-05-10 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.758 _oxdiff_exptl_absorpt_empirical_full_min 0.386 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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 0.44406(13) 0.87991(15) 0.34235(12) 0.0174(3) Uani 1 1 d . O2 O 0.58944(13) 0.89286(15) 0.38023(12) 0.0188(3) Uani 1 1 d . O3 O 0.62883(13) 0.64895(15) 0.39291(11) 0.0170(3) Uani 1 1 d . O10 O 0.39897(14) 0.77832(16) 0.71264(11) 0.0213(3) Uani 1 1 d . N11 N 0.49469(16) 0.69462(18) 0.55164(14) 0.0158(3) Uani 1 1 d . H11 H 0.568(3) 0.668(3) 0.595(2) 0.035(7) Uiso 1 1 d . C1 C 0.39365(19) 0.7331(2) 0.35469(16) 0.0147(4) Uani 1 1 d . C2 C 0.49397(18) 0.6463(2) 0.43154(15) 0.0149(4) Uani 1 1 d . H2 H 0.4625 0.5440 0.4299 0.018 Uiso 1 1 calc R C3 C 0.6614(2) 0.7772(2) 0.33061(17) 0.0184(4) Uani 1 1 d . C4 C 0.6250(2) 0.7610(2) 0.20055(17) 0.0218(4) Uani 1 1 d . H4A H 0.5936 0.8552 0.1696 0.026 Uiso 1 1 calc R H4B H 0.7085 0.7343 0.1600 0.026 Uiso 1 1 calc R C5 C 0.5145(2) 0.6490(2) 0.17279(16) 0.0194(4) Uani 1 1 d . H5A H 0.5516 0.5534 0.1947 0.023 Uiso 1 1 calc R H5B H 0.4962 0.6484 0.0876 0.023 Uiso 1 1 calc R C6 C 0.2968(2) 0.5262(2) 0.23050(17) 0.0200(4) Uani 1 1 d . H6 H 0.3531 0.4532 0.2745 0.024 Uiso 1 1 calc R C7 C 0.1623(2) 0.5431(2) 0.29110(18) 0.0228(4) Uani 1 1 d . H7A H 0.1171 0.4482 0.2952 0.027 Uiso 1 1 calc R H7B H 0.1014 0.6076 0.2444 0.027 Uiso 1 1 calc R C8 C 0.1816(2) 0.6041(2) 0.41390(17) 0.0199(4) Uani 1 1 d . H8A H 0.2351 0.5354 0.4632 0.024 Uiso 1 1 calc R H8B H 0.0913 0.6168 0.4481 0.024 Uiso 1 1 calc R C9 C 0.27556(19) 0.8219(2) 0.53182(17) 0.0166(4) Uani 1 1 d . H9 H 0.3014 0.9237 0.5155 0.020 Uiso 1 1 calc R C10 C 0.39332(19) 0.7600(2) 0.60523(16) 0.0160(4) Uani 1 1 d . C11 C 0.3773(2) 0.6682(2) 0.23154(16) 0.0177(4) Uani 1 1 d . H11A H 0.3224 0.7382 0.1832 0.021 Uiso 1 1 calc R C12 C 0.25624(19) 0.7490(2) 0.41226(16) 0.0158(4) Uani 1 1 d . H12 H 0.1990 0.8150 0.3621 0.019 Uiso 1 1 calc R C13 C 0.8107(2) 0.8083(2) 0.3584(2) 0.0256(5) Uani 1 1 d . H13A H 0.8250 0.8229 0.4423 0.038 Uiso 1 1 calc GR H13B H 0.8378 0.8951 0.3170 0.038 Uiso 1 1 calc GR H13C H 0.8661 0.7269 0.3338 0.038 Uiso 1 1 calc GR C14 C 0.2711(2) 0.4703(2) 0.10674(18) 0.0252(5) Uani 1 1 d . H14A H 0.2227 0.5437 0.0599 0.038 Uiso 1 1 calc GR H14B H 0.2155 0.3829 0.1086 0.038 Uiso 1 1 calc GR H14C H 0.3586 0.4486 0.0723 0.038 Uiso 1 1 calc GR C15 C 0.1454(2) 0.8302(3) 0.60026(19) 0.0256(5) Uani 1 1 d . H15A H 0.0705 0.8674 0.5499 0.038 Uiso 1 1 calc GR H15B H 0.1604 0.8943 0.6670 0.038 Uiso 1 1 calc GR H15C H 0.1218 0.7340 0.6277 0.038 Uiso 1 1 calc GR O20 O 0.71925(14) 0.65940(16) 0.72267(11) 0.0206(3) Uani 1 1 d . O21 O 0.55438(14) 0.63049(16) 0.84944(12) 0.0223(3) Uani 1 1 d . H21 H 0.502(3) 0.686(4) 0.794(3) 0.050(9) Uiso 1 1 d . O22 O 0.95395(15) 0.53982(18) 0.76182(13) 0.0247(3) Uani 1 1 d . H22 H 0.891(3) 0.589(3) 0.730(2) 0.036(8) Uiso 1 1 d . C20 C 0.6769(2) 0.6062(2) 0.81323(16) 0.0183(4) Uani 1 1 d . C21 C 0.7633(2) 0.5105(2) 0.88715(17) 0.0181(4) Uani 1 1 d . C22 C 0.8975(2) 0.4803(2) 0.85602(17) 0.0194(4) Uani 1 1 d . C23 C 0.9775(2) 0.3853(3) 0.92374(18) 0.0240(4) Uani 1 1 d . H23 H 1.0683 0.3644 0.9030 0.029 Uiso 1 1 calc R C24 C 0.9248(2) 0.3219(2) 1.02073(19) 0.0260(5) Uani 1 1 d . H24 H 0.9800 0.2577 1.0664 0.031 Uiso 1 1 calc R C25 C 0.7916(2) 0.3508(2) 1.05258(18) 0.0242(5) Uani 1 1 d . H25 H 0.7560 0.3070 1.1194 0.029 Uiso 1 1 calc R C26 C 0.7123(2) 0.4441(2) 0.98551(17) 0.0208(4) Uani 1 1 d . H26 H 0.6213 0.4637 1.0065 0.025 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 0.0157(6) 0.0114(7) 0.0249(7) 0.0021(5) -0.0008(5) -0.0001(5) O2 0.0153(6) 0.0157(7) 0.0254(7) -0.0036(5) 0.0009(5) -0.0017(5) O3 0.0158(6) 0.0150(7) 0.0202(6) 0.0000(5) 0.0011(5) 0.0019(5) O10 0.0223(7) 0.0245(8) 0.0168(7) -0.0018(6) -0.0004(5) 0.0055(6) N11 0.0145(8) 0.0156(9) 0.0172(8) 0.0008(6) -0.0014(6) 0.0027(6) C1 0.0183(9) 0.0084(9) 0.0173(9) 0.0012(6) -0.0015(7) -0.0003(7) C2 0.0153(9) 0.0132(10) 0.0160(8) 0.0000(7) -0.0009(7) 0.0010(7) C3 0.0181(9) 0.0134(10) 0.0241(10) -0.0026(8) 0.0047(7) 0.0007(8) C4 0.0246(10) 0.0206(11) 0.0205(10) 0.0003(8) 0.0056(7) -0.0010(8) C5 0.0254(10) 0.0165(10) 0.0162(9) -0.0009(7) -0.0003(7) 0.0009(8) C6 0.0227(10) 0.0159(10) 0.0210(10) -0.0019(7) -0.0050(8) 0.0002(8) C7 0.0203(10) 0.0193(11) 0.0283(11) -0.0024(8) -0.0046(8) -0.0026(8) C8 0.0171(9) 0.0182(10) 0.0242(10) 0.0004(8) -0.0003(7) -0.0023(8) C9 0.0159(9) 0.0148(10) 0.0191(9) 0.0003(7) -0.0002(7) 0.0014(7) C10 0.0162(9) 0.0131(10) 0.0188(9) 0.0004(7) 0.0010(7) -0.0012(7) C11 0.0199(9) 0.0162(10) 0.0168(9) 0.0004(7) -0.0027(7) 0.0021(7) C12 0.0159(9) 0.0128(10) 0.0184(9) 0.0013(7) -0.0022(7) 0.0015(7) C13 0.0203(11) 0.0251(12) 0.0318(11) -0.0075(9) 0.0048(8) -0.0029(8) C14 0.0290(11) 0.0205(11) 0.0254(11) -0.0033(8) -0.0076(8) -0.0003(9) C15 0.0185(10) 0.0341(13) 0.0243(11) -0.0034(8) 0.0009(8) 0.0042(9) O20 0.0221(7) 0.0187(7) 0.0208(7) 0.0010(5) -0.0022(5) -0.0003(6) O21 0.0204(7) 0.0253(9) 0.0211(7) -0.0008(6) 0.0001(5) 0.0057(6) O22 0.0188(7) 0.0300(9) 0.0255(8) 0.0061(6) 0.0016(6) 0.0012(6) C20 0.0211(10) 0.0148(10) 0.0186(9) -0.0068(7) -0.0033(7) -0.0005(7) C21 0.0207(10) 0.0150(10) 0.0183(9) -0.0053(7) -0.0032(7) -0.0011(7) C22 0.0213(10) 0.0184(11) 0.0185(9) -0.0027(7) -0.0018(7) -0.0027(8) C23 0.0184(10) 0.0274(12) 0.0257(10) -0.0017(9) -0.0027(8) 0.0024(9) C24 0.0273(11) 0.0255(12) 0.0245(11) 0.0025(8) -0.0079(9) 0.0036(9) C25 0.0304(11) 0.0251(12) 0.0170(10) -0.0001(8) -0.0014(8) -0.0009(9) C26 0.0219(10) 0.0222(11) 0.0183(9) -0.0050(8) -0.0001(7) 0.0014(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C1 O1 O2 111.90(13) C3 O2 O1 107.94(13) C2 O3 C3 113.72(14) C10 N11 C2 127.21(16) O1 C1 C2 109.82(15) O1 C1 C11 107.42(15) O1 C1 C12 104.96(14) C2 C1 C11 111.44(15) C2 C1 C12 110.89(15) C12 C1 C11 112.03(15) O3 C2 N11 109.00(14) O3 C2 C1 113.37(15) N11 C2 C1 111.45(15) O2 C3 O3 107.78(14) O2 C3 C4 111.58(16) O2 C3 C13 105.20(16) O3 C3 C4 111.00(16) O3 C3 C13 106.62(16) C13 C3 C4 114.25(16) C5 C4 C3 114.01(16) C4 C5 C11 116.92(16) C7 C6 C11 111.15(16) C7 C6 C14 110.43(17) C14 C6 C11 111.39(17) C6 C7 C8 112.61(16) C7 C8 C12 110.90(16) C10 C9 C12 113.22(16) C10 C9 C15 111.32(16) C15 C9 C12 114.10(16) O10 C10 N11 121.05(18) O10 C10 C9 120.21(17) N11 C10 C9 118.58(16) C5 C11 C1 112.92(15) C5 C11 C6 110.70(16) C6 C11 C1 112.16(16) C1 C12 C8 110.36(15) C1 C12 C9 110.55(15) C8 C12 C9 114.71(15) O20 C20 O21 122.80(18) O20 C20 C21 121.49(18) O21 C20 C21 115.71(18) C22 C21 C20 119.65(18) C26 C21 C20 121.18(18) C26 C21 C22 119.12(18) O22 C22 C21 122.57(19) O22 C22 C23 117.84(18) C23 C22 C21 119.58(19) C24 C23 C22 120.10(19) C23 C24 C25 120.9(2) C26 C25 C24 119.1(2) C25 C26 C21 121.24(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 O2 1.4772(18) O1 C1 1.462(2) O2 C3 1.419(2) O3 C2 1.411(2) O3 C3 1.436(2) O10 C10 1.247(2) N11 C2 1.454(2) N11 C10 1.336(3) C1 C2 1.527(2) C1 C11 1.543(3) C1 C12 1.531(3) C3 C4 1.533(3) C3 C13 1.512(3) C4 C5 1.527(3) C5 C11 1.538(3) C6 C7 1.523(3) C6 C11 1.539(3) C6 C14 1.528(3) C7 C8 1.528(3) C8 C12 1.534(3) C9 C10 1.516(3) C9 C12 1.540(3) C9 C15 1.527(3) O20 C20 1.241(2) O21 C20 1.306(2) O22 C22 1.355(3) C20 C21 1.475(3) C21 C22 1.405(3) C21 C26 1.400(3) C22 C23 1.398(3) C23 C24 1.381(3) C24 C25 1.396(3) C25 C26 1.380(3) 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 N11 H11 O20 0.89(3) 2.05(3) 2.911(2) 163(3) O21 H21 O10 0.95(4) 1.60(4) 2.5490(19) 173(3) O22 H22 O20 0.84(3) 1.81(3) 2.577(2) 152(3) 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 O1 O2 C3 O3 -74.26(16) O1 O2 C3 C4 47.85(19) O1 O2 C3 C13 172.26(14) O1 C1 C2 O3 -54.1(2) O1 C1 C2 N11 69.29(19) O1 C1 C11 C5 66.16(19) O1 C1 C11 C6 -167.93(15) O1 C1 C12 C8 171.55(15) O1 C1 C12 C9 -60.48(18) O2 O1 C1 C2 14.66(19) O2 O1 C1 C11 -106.70(15) O2 O1 C1 C12 133.91(13) O2 C3 C4 C5 -96.2(2) O3 C3 C4 C5 24.0(2) C1 O1 O2 C3 46.36(17) C2 O3 C3 O2 34.0(2) C2 O3 C3 C4 -88.51(18) C2 O3 C3 C13 146.48(15) C2 N11 C10 O10 169.84(19) C2 N11 C10 C9 -14.7(3) C2 C1 C11 C5 -54.2(2) C2 C1 C11 C6 71.7(2) C2 C1 C12 C8 -69.92(19) C2 C1 C12 C9 58.1(2) C3 O3 C2 N11 -96.23(17) C3 O3 C2 C1 28.5(2) C3 C4 C5 C11 56.3(2) C4 C5 C11 C1 -33.9(2) C4 C5 C11 C6 -160.56(17) C6 C7 C8 C12 56.7(2) C7 C6 C11 C1 51.5(2) C7 C6 C11 C5 178.62(16) C7 C8 C12 C1 -56.6(2) C7 C8 C12 C9 177.72(16) C10 N11 C2 O3 151.69(18) C10 N11 C2 C1 25.8(3) C10 C9 C12 C1 -46.2(2) C10 C9 C12 C8 79.4(2) C11 C1 C2 O3 64.8(2) C11 C1 C2 N11 -171.80(15) C11 C1 C12 C8 55.29(19) C11 C1 C12 C9 -176.73(15) C11 C6 C7 C8 -53.7(2) C12 C1 C2 O3 -169.68(14) C12 C1 C2 N11 -46.3(2) C12 C1 C11 C5 -179.08(15) C12 C1 C11 C6 -53.2(2) C12 C9 C10 O10 -160.19(17) C12 C9 C10 N11 24.4(2) C13 C3 C4 C5 144.59(18) C14 C6 C7 C8 -177.87(18) C14 C6 C11 C1 175.12(16) C14 C6 C11 C5 -57.8(2) C15 C9 C10 O10 -30.1(3) C15 C9 C10 N11 154.46(18) C15 C9 C12 C1 -174.86(16) C15 C9 C12 C8 -49.3(2) O20 C20 C21 C22 1.1(3) O20 C20 C21 C26 -176.24(18) O21 C20 C21 C22 -178.88(17) O21 C20 C21 C26 3.8(3) O22 C22 C23 C24 179.9(2) C20 C21 C22 O22 2.4(3) C20 C21 C22 C23 -177.60(18) C20 C21 C26 C25 177.83(19) C21 C22 C23 C24 -0.1(3) C22 C21 C26 C25 0.5(3) C22 C23 C24 C25 0.2(3) C23 C24 C25 C26 0.1(3) C24 C25 C26 C21 -0.4(3) C26 C21 C22 O22 179.75(18) C26 C21 C22 C23 -0.2(3)