#------------------------------------------------------------------------------ #$Date: 2016-03-26 14:45:17 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180275 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/61/7116125.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_7116125 loop_ _publ_author_name 'Giannis S. Papaefstathiou' 'Andrew J. E. Duncan' 'Leonard R. MacGillivray' _publ_section_title ; Two act as one: unexpected dimers of catechol direct a solid-state [2+2] photodimerization in a six-component hydrogen-bonded assembly ; _journal_name_full Chem.Commun. _journal_page_first 15960 _journal_paper_doi 10.1039/C4cc07747D _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C12 H10 N2, 2(C6 H6 O2)' _chemical_formula_sum 'C24 H22 N2 O4' _chemical_formula_weight 402.43 _chemical_name_common 'catechol, 2,2'-bpe' _chemical_name_systematic ; 1,2-dihydroxybenzene, 1,2-bis(2-pyridyl)ethylene ; _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 2014-09-17 _audit_creation_method ; Olex2 1.2 (compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874) ; _cell_angle_alpha 90 _cell_angle_beta 102.277(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3687(7) _cell_length_b 19.169(2) _cell_length_c 14.7014(15) _cell_measurement_reflns_used 8707 _cell_measurement_temperature 190(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1.00 _cell_volume 2029.1(4) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_data_reduction ; HKL Denzo, 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, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 190.15 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_unetI/netI 0.0370 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 16490 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.241 _diffrn_reflns_theta_max 27.483 _diffrn_reflns_theta_min 1.771 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.317 _exptl_crystal_description needle _exptl_crystal_F_000 848 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Acetonitrile' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.332 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.118 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 287 _refine_ls_number_reflns 4648 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.101 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0425 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0897P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1164 _refine_ls_wR_factor_ref 0.1485 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3329 _reflns_number_total 4648 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c4cc07747d2.cif _cod_data_source_block mcg466 _cod_database_code 7116125 #BEGIN Tags that were not found in dictionaries: _shelxl_version_number 2014/6 _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 0.991 _shelx_estimated_absorpt_t_min 0.966 _olex2_refinement_description ; 1. Others Fixed Uiso: H1(0.044) H2(0.049) H3(0.049) H4(0.042) H6(0.035) H7(0.034) H9(0.036) H10(0.041) H11(0.043) H12(0.042) H15(0.042) H16(0.049) H17(0.049) H18(0.046) H21(0.041) H22(0.048) H23(0.048) H24(0.042) Fixed X: H1(0.2926) H2(0.3399) H3(0.3575) H4(0.3181) H6(0.2244) H7(0.2802) H9(0.1669) H10(0.1176) H11(0.1432) H12(0.2221) H15(-0.0517) H16(-0.0502) H17(0.2329) H18(0.5095) H21(0.9222) H22(1.0142) H23(0.8159) H24(0.5296) Fixed Y: H1(0.1963) H2(0.1333) H3(0.0113) H4(-0.0441) H6(0.0494) H7(-0.0831) H9(0.0164) H10(-0.0322) H11(-0.1539) H12(-0.2214) H15(0.1877) H16(0.1499) H17(0.122) H18(0.1308) H21(0.2815) H22(0.3983) H23(0.484) H24(0.4525) Fixed Z: H1(0.8131) H2(0.6853) H3(0.6955) H4(0.8313) H6(1.0327) H7(0.9697) H9(1.1606) H10(1.2988) H11(1.3205) H12(1.2043) H15(1.1053) H16(1.2561) H17(1.3564) H18(1.3047) H21(0.959) H22(0.9671) H23(1.0034) H24(1.0345) ; _shelx_res_file ; TITL 4(cat).2(2,2'-bpe) P2(1)/c CELL 0.7107 7.3687 19.169 14.7014 90 102.277 90 ZERR 4 0.0007 0.002 0.0015 0 0.005 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 96 88 8 16 EQIV $1 1-X,-Y,2-Z DFIX 0.84 O3 H3a L.S. 4 PLAN 20 SIZE 0.38 0.1 0.1 TEMP -83 HTAB O4 O1 HTAB O1 N1 HTAB O2 O3 HTAB O3 N2_$1 fmap 2 acta MERG 2 REM /Users/Jake/Documents/Research/Working%20Structures/from%20WinGX/mcg4 REM -66/mcg466.hkl WGHT 0.089700 FVAR 0.23365 C1 1 0.297205 0.146814 0.816654 11.00000 0.03566 0.04001 = 0.03320 0.00779 0.00729 -0.00483 AFIX 43 H1 2 0.292620 0.196287 0.813081 11.00000 -1.20000 AFIX 0 C2 1 0.326416 0.109906 0.740407 11.00000 0.03546 0.06007 = 0.02860 0.00859 0.00918 -0.00473 AFIX 43 H2 2 0.339908 0.133310 0.685269 11.00000 -1.20000 AFIX 0 C3 1 0.335489 0.038088 0.746445 11.00000 0.03619 0.05854 = 0.02832 -0.00354 0.01054 0.00086 AFIX 43 H3 2 0.357533 0.011347 0.695471 11.00000 -1.20000 AFIX 0 C4 1 0.312503 0.005335 0.826536 11.00000 0.03240 0.04145 = 0.03111 -0.00268 0.00867 0.00108 AFIX 43 H4 2 0.318098 -0.044074 0.831339 11.00000 -1.20000 AFIX 0 C5 1 0.280885 0.045705 0.900533 11.00000 0.02322 0.03280 = 0.02673 0.00084 0.00460 -0.00138 C6 1 0.250078 0.016732 0.988443 11.00000 0.03097 0.03231 = 0.02594 -0.00259 0.00712 0.00052 AFIX 43 H6 2 0.224361 0.049370 1.032670 11.00000 -1.20000 AFIX 0 C7 1 0.254126 -0.049780 1.012975 11.00000 0.02757 0.03079 = 0.02899 -0.00355 0.00873 -0.00080 AFIX 43 H7 2 0.280155 -0.083114 0.969661 11.00000 -1.20000 AFIX 0 C8 1 0.221506 -0.076022 1.101934 11.00000 0.02198 0.02929 = 0.02839 -0.00108 0.00443 -0.00014 C9 1 0.177054 -0.032601 1.170309 11.00000 0.02985 0.03062 = 0.03053 -0.00118 0.00610 0.00245 AFIX 43 H9 2 0.166912 0.016365 1.160587 11.00000 -1.20000 AFIX 0 C10 1 0.148052 -0.061247 1.251856 11.00000 0.03091 0.04485 = 0.02783 -0.00322 0.00793 0.00184 AFIX 43 H10 2 0.117604 -0.032201 1.298800 11.00000 -1.20000 AFIX 0 C11 1 0.163601 -0.132916 1.265056 11.00000 0.03286 0.04647 = 0.02798 0.00435 0.00765 -0.00425 AFIX 43 H11 2 0.143153 -0.153945 1.320527 11.00000 -1.20000 AFIX 0 C12 1 0.209519 -0.172413 1.195283 11.00000 0.03691 0.03239 = 0.03626 0.00399 0.01088 -0.00164 AFIX 43 H12 2 0.222059 -0.221395 1.204300 11.00000 -1.20000 AFIX 0 C14 1 0.226131 0.181534 1.114042 11.00000 0.03385 0.02790 = 0.02773 -0.00383 0.00912 -0.00152 C15 1 0.062754 0.176028 1.145753 11.00000 0.02920 0.03769 = 0.03858 -0.00295 0.00797 -0.00166 AFIX 43 H15 2 -0.051692 0.187737 1.105256 11.00000 -1.20000 AFIX 0 C16 1 0.063010 0.153776 1.235377 11.00000 0.03981 0.04715 = 0.04050 -0.00566 0.01955 -0.00509 AFIX 43 H16 2 -0.050179 0.149926 1.256137 11.00000 -1.20000 AFIX 0 C17 1 0.231045 0.137123 1.294671 11.00000 0.04978 0.04765 = 0.02793 -0.00505 0.01342 -0.00581 AFIX 43 H17 2 0.232933 0.121964 1.356388 11.00000 -1.20000 AFIX 0 C18 1 0.395363 0.142591 1.263953 11.00000 0.03757 0.04655 = 0.02912 -0.00309 0.00380 -0.00141 AFIX 43 H18 2 0.509529 0.130841 1.304662 11.00000 -1.20000 AFIX 0 C13 1 0.394874 0.164990 1.174588 11.00000 0.03016 0.03314 = 0.03197 -0.00389 0.01036 -0.00065 C20 1 0.668971 0.297797 0.989299 11.00000 0.03421 0.02356 = 0.02512 0.00016 0.00610 0.00118 C21 1 0.841325 0.316408 0.973440 11.00000 0.03331 0.03285 = 0.03704 -0.00169 0.01181 0.00262 AFIX 43 H21 2 0.922193 0.281487 0.958952 11.00000 -1.20000 AFIX 0 C22 1 0.896343 0.385676 0.978601 11.00000 0.03881 0.03799 = 0.04526 -0.00102 0.01434 -0.00757 AFIX 43 H22 2 1.014151 0.398273 0.967138 11.00000 -1.20000 AFIX 0 C23 1 0.779263 0.436387 1.000481 11.00000 0.05063 0.02804 = 0.04424 0.00135 0.01453 -0.00523 AFIX 43 H23 2 0.815870 0.483995 1.003429 11.00000 -1.20000 AFIX 0 C24 1 0.608498 0.417660 1.018096 11.00000 0.04472 0.02611 = 0.03438 0.00257 0.00985 0.00759 AFIX 43 H24 2 0.529564 0.452531 1.034459 11.00000 -1.20000 AFIX 0 C19 1 0.551883 0.349073 1.012156 11.00000 0.03113 0.02918 = 0.02218 0.00329 0.00638 0.00409 N1 3 0.275024 0.116140 0.895441 11.00000 0.03194 0.03489 = 0.02803 0.00204 0.00732 -0.00381 N2 3 0.237632 -0.145595 1.115082 11.00000 0.03240 0.02834 = 0.03149 0.00012 0.00973 -0.00137 O1 4 0.225484 0.205997 1.025665 11.00000 0.03842 0.03158 = 0.02978 0.00234 0.00923 0.00120 O2 4 0.560892 0.170185 1.147617 11.00000 0.03086 0.05671 = 0.04107 0.00834 0.01237 0.00595 O3 4 0.605841 0.230425 0.985433 11.00000 0.04037 0.02520 = 0.04409 -0.00434 0.02156 -0.00108 O4 4 0.382029 0.333699 1.029635 11.00000 0.03619 0.03133 = 0.03999 -0.00237 0.01559 0.00285 H2A 2 0.555031 0.187949 1.090979 11.00000 0.06275 H1A 2 0.243806 0.167452 0.984021 11.00000 0.06961 H4A 2 0.352920 0.287318 1.020338 11.00000 0.07252 H3A 2 0.669637 0.202303 0.953163 11.00000 0.07400 HKLF 4 REM 4(cat).2(2,2'-bpe) P2(1)/c REM R1 = 0.0425 for 3329 Fo > 4sig(Fo) and 0.0739 for all 4648 data REM 287 parameters refined using 1 restraints END WGHT 0.0799 0.0000 REM Highest difference peak 0.332, deepest hole -0.320, 1-sigma level 0.118 Q1 1 -0.0542 0.1076 1.2976 11.00000 0.05 0.33 Q2 1 -0.0214 0.0625 1.3156 11.00000 0.05 0.31 Q3 1 -0.0873 0.0541 1.3213 11.00000 0.05 0.31 Q4 1 0.9951 0.3679 0.8919 11.00000 0.05 0.30 Q5 1 0.9185 0.4037 0.8593 11.00000 0.05 0.30 Q6 1 0.0264 0.0306 1.3549 11.00000 0.05 0.30 Q7 1 0.9482 0.4205 0.8928 11.00000 0.05 0.30 Q8 1 -0.0501 0.0476 1.2626 11.00000 0.05 0.29 Q9 1 -0.0579 -0.0022 1.3069 11.00000 0.05 0.29 Q10 1 0.9979 0.4088 0.8546 11.00000 0.05 0.29 Q11 1 0.9789 0.4566 0.8980 11.00000 0.05 0.28 Q12 1 -0.0756 0.0094 1.3430 11.00000 0.05 0.28 Q13 1 0.1614 0.0965 1.3724 11.00000 0.05 0.28 Q14 1 1.0290 0.5016 1.0785 11.00000 0.05 0.27 Q15 1 1.0003 0.5136 1.0651 11.00000 0.05 0.27 Q16 1 0.1517 0.1313 1.2568 11.00000 0.05 0.27 Q17 1 0.1153 0.0615 1.3072 11.00000 0.05 0.27 Q18 1 0.1110 0.0756 1.3223 11.00000 0.05 0.27 Q19 1 0.0054 0.1605 1.3159 11.00000 0.05 0.27 Q20 1 0.0634 0.0799 1.2513 11.00000 0.05 0.26 ; _shelx_res_checksum 43386 _olex2_submission_special_instructions 'No special instructions were received' #END Tags that were not found in dictionaries 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 C1 C 0.2972(2) 0.14681(9) 0.81665(11) 0.0363(4) Uani 1 1 d . H1 H 0.2926 0.1963 0.8131 0.044 Uiso 1 1 calc R C2 C 0.3264(2) 0.10991(10) 0.74041(11) 0.0410(4) Uani 1 1 d . H2 H 0.3399 0.1333 0.6853 0.049 Uiso 1 1 calc R C3 C 0.3355(2) 0.03809(10) 0.74644(11) 0.0405(4) Uani 1 1 d . H3 H 0.3575 0.0113 0.6955 0.049 Uiso 1 1 calc R C4 C 0.31250(19) 0.00534(9) 0.82654(11) 0.0347(4) Uani 1 1 d . H4 H 0.3181 -0.0441 0.8313 0.042 Uiso 1 1 calc R C5 C 0.28089(19) 0.04571(8) 0.90053(10) 0.0277(3) Uani 1 1 d . C6 C 0.25008(19) 0.01673(8) 0.98844(10) 0.0296(3) Uani 1 1 d . H6 H 0.2244 0.0494 1.0327 0.035 Uiso 1 1 calc R C7 C 0.25413(19) -0.04978(8) 1.01297(10) 0.0287(3) Uani 1 1 d . H7 H 0.2802 -0.0831 0.9697 0.034 Uiso 1 1 calc R C8 C 0.22151(18) -0.07602(8) 1.10193(10) 0.0267(3) Uani 1 1 d . C9 C 0.17705(19) -0.03260(9) 1.17031(10) 0.0304(4) Uani 1 1 d . H9 H 0.1669 0.0164 1.1606 0.036 Uiso 1 1 calc R C10 C 0.1481(2) -0.06125(9) 1.25186(11) 0.0343(4) Uani 1 1 d . H10 H 0.1176 -0.0322 1.2988 0.041 Uiso 1 1 calc R C11 C 0.1636(2) -0.13292(9) 1.26506(11) 0.0356(4) Uani 1 1 d . H11 H 0.1432 -0.1539 1.3205 0.043 Uiso 1 1 calc R C12 C 0.2095(2) -0.17241(9) 1.19528(11) 0.0347(4) Uani 1 1 d . H12 H 0.2221 -0.2214 1.2043 0.042 Uiso 1 1 calc R C14 C 0.2261(2) 0.18153(8) 1.11404(10) 0.0294(3) Uani 1 1 d . C15 C 0.0628(2) 0.17603(8) 1.14575(11) 0.0350(4) Uani 1 1 d . H15 H -0.0517 0.1877 1.1053 0.042 Uiso 1 1 calc R C16 C 0.0630(2) 0.15378(10) 1.23538(12) 0.0409(4) Uani 1 1 d . H16 H -0.0502 0.1499 1.2561 0.049 Uiso 1 1 calc R C17 C 0.2310(2) 0.13712(9) 1.29467(12) 0.0410(4) Uani 1 1 d . H17 H 0.2329 0.1220 1.3564 0.049 Uiso 1 1 calc R C18 C 0.3954(2) 0.14259(9) 1.26395(11) 0.0382(4) Uani 1 1 d . H18 H 0.5095 0.1308 1.3047 0.046 Uiso 1 1 calc R C13 C 0.3949(2) 0.16499(8) 1.17459(11) 0.0312(4) Uani 1 1 d . C20 C 0.6690(2) 0.29780(8) 0.98930(10) 0.0277(3) Uani 1 1 d . C21 C 0.8413(2) 0.31641(9) 0.97344(11) 0.0338(4) Uani 1 1 d . H21 H 0.9222 0.2815 0.9590 0.041 Uiso 1 1 calc R C22 C 0.8963(2) 0.38568(9) 0.97860(12) 0.0399(4) Uani 1 1 d . H22 H 1.0142 0.3983 0.9671 0.048 Uiso 1 1 calc R C23 C 0.7793(2) 0.43639(9) 1.00048(12) 0.0403(4) Uani 1 1 d . H23 H 0.8159 0.4840 1.0034 0.048 Uiso 1 1 calc R C24 C 0.6085(2) 0.41766(8) 1.01810(11) 0.0349(4) Uani 1 1 d . H24 H 0.5296 0.4525 1.0345 0.042 Uiso 1 1 calc R C19 C 0.55188(19) 0.34907(8) 1.01216(10) 0.0274(3) Uani 1 1 d . N1 N 0.27502(17) 0.11614(7) 0.89544(9) 0.0315(3) Uani 1 1 d . N2 N 0.23763(16) -0.14559(7) 1.11508(9) 0.0303(3) Uani 1 1 d . O1 O 0.22548(14) 0.20600(6) 1.02567(7) 0.0330(3) Uani 1 1 d . O2 O 0.56089(14) 0.17018(7) 1.14762(9) 0.0422(3) Uani 1 1 d . O3 O 0.60584(15) 0.23043(6) 0.98543(8) 0.0347(3) Uani 1 1 d D O4 O 0.38203(15) 0.33370(6) 1.02964(8) 0.0347(3) Uani 1 1 d . H2A H 0.555(3) 0.1879(11) 1.0910(16) 0.063(7) Uiso 1 1 d . H1A H 0.244(3) 0.1675(12) 0.9840(16) 0.070(7) Uiso 1 1 d . H4A H 0.353(3) 0.2873(14) 1.0203(16) 0.073(7) Uiso 1 1 d . H3A H 0.670(3) 0.2023(11) 0.9532(15) 0.074(7) Uiso 1 1 d 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 0.0357(9) 0.0400(10) 0.0332(9) 0.0078(7) 0.0073(6) -0.0048(7) C2 0.0355(9) 0.0601(13) 0.0286(9) 0.0086(8) 0.0092(7) -0.0047(8) C3 0.0362(9) 0.0585(12) 0.0283(9) -0.0035(8) 0.0105(6) 0.0009(8) C4 0.0324(8) 0.0415(10) 0.0311(9) -0.0027(7) 0.0087(6) 0.0011(7) C5 0.0232(7) 0.0328(9) 0.0267(8) 0.0008(6) 0.0046(5) -0.0014(6) C6 0.0310(8) 0.0323(9) 0.0259(8) -0.0026(6) 0.0071(6) 0.0005(6) C7 0.0276(8) 0.0308(9) 0.0290(8) -0.0035(6) 0.0087(6) -0.0008(6) C8 0.0220(7) 0.0293(8) 0.0284(8) -0.0011(6) 0.0044(5) -0.0001(6) C9 0.0299(8) 0.0306(9) 0.0305(8) -0.0012(7) 0.0061(6) 0.0025(6) C10 0.0309(8) 0.0448(10) 0.0278(8) -0.0032(7) 0.0079(6) 0.0018(7) C11 0.0329(8) 0.0465(11) 0.0280(8) 0.0043(7) 0.0077(6) -0.0042(7) C12 0.0369(9) 0.0324(9) 0.0363(9) 0.0040(7) 0.0109(7) -0.0016(6) C14 0.0339(8) 0.0279(8) 0.0277(8) -0.0038(6) 0.0091(6) -0.0015(6) C15 0.0292(8) 0.0377(10) 0.0386(9) -0.0030(7) 0.0080(6) -0.0017(6) C16 0.0398(10) 0.0472(11) 0.0405(10) -0.0057(8) 0.0196(7) -0.0051(7) C17 0.0498(10) 0.0476(11) 0.0279(9) -0.0051(7) 0.0134(7) -0.0058(8) C18 0.0376(9) 0.0465(11) 0.0291(9) -0.0031(7) 0.0038(6) -0.0014(7) C13 0.0302(8) 0.0331(9) 0.0320(9) -0.0039(7) 0.0104(6) -0.0007(6) C20 0.0342(8) 0.0236(8) 0.0251(8) 0.0002(6) 0.0061(6) 0.0012(6) C21 0.0333(8) 0.0329(9) 0.0370(9) -0.0017(7) 0.0118(6) 0.0026(7) C22 0.0388(9) 0.0380(10) 0.0453(10) -0.0010(8) 0.0143(7) -0.0076(7) C23 0.0506(10) 0.0280(9) 0.0442(10) 0.0014(7) 0.0145(8) -0.0052(7) C24 0.0447(9) 0.0261(9) 0.0344(9) 0.0026(7) 0.0099(7) 0.0076(7) C19 0.0311(8) 0.0292(8) 0.0222(7) 0.0033(6) 0.0064(6) 0.0041(6) N1 0.0319(7) 0.0349(8) 0.0280(7) 0.0020(6) 0.0073(5) -0.0038(5) N2 0.0324(7) 0.0283(7) 0.0315(7) 0.0001(5) 0.0097(5) -0.0014(5) O1 0.0384(6) 0.0316(6) 0.0298(6) 0.0023(5) 0.0092(4) 0.0012(5) O2 0.0309(6) 0.0567(9) 0.0411(7) 0.0083(6) 0.0124(5) 0.0060(5) O3 0.0404(6) 0.0252(6) 0.0441(7) -0.0043(5) 0.0216(5) -0.0011(4) O4 0.0362(6) 0.0313(7) 0.0400(7) -0.0024(5) 0.0156(5) 0.0029(5) 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 N1 C1 C2 123.08(17) C3 C2 C1 118.21(15) C4 C3 C2 119.80(16) C3 C4 C5 119.06(17) C4 C5 C6 124.03(15) N1 C5 C4 121.30(14) N1 C5 C6 114.67(13) C7 C6 C5 127.27(14) C6 C7 C8 125.06(14) C9 C8 C7 123.02(14) N2 C8 C7 116.12(13) N2 C8 C9 120.86(14) C10 C9 C8 119.53(15) C9 C10 C11 119.54(15) C12 C11 C10 117.83(15) N2 C12 C11 123.60(15) C15 C14 C13 119.08(14) O1 C14 C15 120.91(13) O1 C14 C13 119.95(13) C14 C15 C16 121.24(15) C15 C16 C17 119.20(15) C18 C17 C16 120.15(15) C13 C18 C17 120.57(15) C18 C13 C14 119.76(14) O2 C13 C14 121.76(14) O2 C13 C18 118.48(14) C21 C20 C19 119.66(14) O3 C20 C21 123.44(13) O3 C20 C19 116.89(13) C22 C21 C20 120.36(14) C23 C22 C21 119.79(15) C22 C23 C24 119.87(16) C19 C24 C23 120.72(15) C24 C19 C20 119.57(14) O4 C19 C20 122.21(14) O4 C19 C24 118.22(13) C1 N1 C5 118.54(14) C12 N2 C8 118.63(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.381(2) C1 N1 1.340(2) C2 C3 1.380(3) C3 C4 1.376(2) C4 C5 1.394(2) C5 C6 1.468(2) C5 N1 1.3524(19) C6 C7 1.324(2) C7 C8 1.468(2) C8 C9 1.397(2) C8 N2 1.3492(19) C9 C10 1.376(2) C10 C11 1.389(2) C11 C12 1.374(2) C12 N2 1.342(2) C14 C15 1.384(2) C14 C13 1.403(2) C14 O1 1.3804(18) C15 C16 1.385(2) C16 C17 1.391(2) C17 C18 1.383(2) C18 C13 1.381(2) C13 O2 1.3675(18) C20 C21 1.386(2) C20 C19 1.395(2) C20 O3 1.3697(18) C21 C22 1.386(2) C22 C23 1.382(2) C23 C24 1.385(2) C24 C19 1.376(2) C19 O4 1.3624(18) 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 H2A O3 0.89(2) 1.86(2) 2.7320(17) 165(2) . O1 H1A N1 0.99(2) 1.69(2) 2.6576(17) 167(2) . O4 H4A O1 0.92(3) 1.83(3) 2.7014(17) 158(2) . O3 H3A N2 0.912(16) 1.717(16) 2.6236(16) 173(2) 3_657