#------------------------------------------------------------------------------ #$Date: 2016-03-26 14:45:17 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180275 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/61/7116127.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_7116127 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 '2(C12 H10 N2), 3(C6 H6 O2)' _chemical_formula_sum 'C42 H38 N4 O6' _chemical_formula_weight 694.76 _chemical_name_common 'catechol, 2,2'-tpcb' _chemical_name_systematic ; 1,2-dihydroxybenzene, rctt-tetrakis(2-pyridyl)cyclobutane ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2014-09-18 _audit_creation_method ; Olex2 1.2 (compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874) ; _cell_angle_alpha 109.918(5) _cell_angle_beta 103.137(5) _cell_angle_gamma 102.958(5) _cell_formula_units_Z 2 _cell_length_a 11.9841(12) _cell_length_b 12.6106(13) _cell_length_c 13.7902(14) _cell_measurement_reflns_used 5559 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.11 _cell_measurement_theta_min 1.00 _cell_volume 1801.6(3) _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)' _diffrn_ambient_temperature 293.15 _diffrn_measured_fraction_theta_full 0.874 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_unetI/netI 0.0337 _diffrn_reflns_Laue_measured_fraction_full 0.874 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9665 _diffrn_reflns_point_group_measured_fraction_full 0.874 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 24.096 _diffrn_reflns_theta_min 1.665 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.281 _exptl_crystal_description plate _exptl_crystal_F_000 732 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Nitromethane' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.294 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.100 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 493 _refine_ls_number_reflns 5711 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.139 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0512 _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^)+(0.1084P)^2^+0.0953P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1451 _refine_ls_wR_factor_ref 0.1776 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4235 _reflns_number_total 5711 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c4cc07747d2.cif _cod_data_source_block mcg1323 _cod_database_code 7116127 #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 0.990 _shelx_estimated_absorpt_t_min 0.972 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2. Restrained distances O1-H1A 0.84 with sigma of 0.02 O2-H2A 0.84 with sigma of 0.02 O3-H3A 0.84 with sigma of 0.02 O4-H4A 0.84 with sigma of 0.02 O5-H5 0.84 with sigma of 0.02 O6-H6A 0.84 with sigma of 0.02 3.a Ternary CH refined with riding coordinates: C18(H18), C19(H19), C7(H7), C6(H6) 3.b Aromatic/amide H refined with riding coordinates: C16(H16), C21(H21), C4(H4), C9(H9), C27(H27), C30(H30), C28(H28), C29(H29), C15(H15), C14(H14), C13(H13), C42(H42), C24(H24), C39(H39), C23(H23), C22(H22), C41(H41), C40(H40), C36(H36), C35(H35), C12(H12), C11(H11), C10(H10), C3(H3), C1(H1), C2(H2), C34(H34), C33(H33) ; _shelx_res_file ; TITL 3(cat).(2,2'-tpcb) in P-1 CELL 0.71073 11.9841 12.6106 13.7902 109.918 103.137 102.958 ZERR 2 0.0012 0.0013 0.0014 0.005 0.005 0.005 LATT 1 SFAC C H N O UNIT 84 76 8 12 EQIV $1 -1+X,+Y,+Z EQIV $2 -1+X,-1+Y,+Z EQIV $3 +X,1+Y,+Z EQIV $4 +X,-1+Y,+Z DFIX 0.84 O1 H1a DFIX 0.84 O2 H2a DFIX 0.84 O3 H3a DFIX 0.84 O4 H4a DFIX 0.84 O5 H5 DFIX 0.84 O6 H6a L.S. 10 PLAN 20 SIZE 0.12 0.3 0.33 TEMP 20 HTAB O4 N3_$1 HTAB O1 N2_$2 HTAB O3 O1 HTAB O6 O3_$3 HTAB O2 O5_$4 BOND fmap 2 acta MERG 2 OMIT -2 50.1 REM /Users/Jake/Documents/Research/Working%20Structures/from%20WinGX/mcg1 REM 3-23/mcg1323.hkl WGHT 0.108400 0.095300 FVAR 0.45174 N1 3 1.509904 0.806561 0.129996 11.00000 0.05304 0.05249 = 0.04794 0.02079 0.02182 0.02199 N2 3 1.427744 1.073863 0.225875 11.00000 0.05088 0.06608 = 0.04533 0.01691 0.02207 0.01895 C16 1 1.326370 0.799159 0.012099 11.00000 0.04557 0.05125 = 0.05086 0.01629 0.01633 0.01472 AFIX 43 H16 2 1.287292 0.828133 -0.034457 11.00000 -1.20000 AFIX 0 C21 1 1.292186 1.086652 0.079148 11.00000 0.05675 0.08443 = 0.05999 0.03184 0.02748 0.03779 AFIX 43 H21 2 1.275840 1.090692 0.011505 11.00000 -1.20000 AFIX 0 N4 3 1.367315 0.305285 0.531462 11.00000 0.05906 0.05993 = 0.06215 0.02956 0.02265 0.01553 C4 1 1.376433 0.415380 0.238513 11.00000 0.06808 0.07806 = 0.05357 0.02119 0.02124 0.02231 AFIX 43 H4 2 1.308282 0.415120 0.260043 11.00000 -1.20000 AFIX 0 N3 3 1.582528 0.424899 0.281781 11.00000 0.06968 0.05758 = 0.06177 0.01789 0.03808 0.01921 C9 1 1.192054 0.351823 0.462564 11.00000 0.04456 0.07381 = 0.05935 0.02701 0.01689 0.01158 AFIX 43 H9 2 1.158790 0.399708 0.434899 11.00000 -1.20000 AFIX 0 H6A 2 0.890326 1.015700 0.176661 11.00000 0.10637 H5 2 0.675288 0.867873 0.196741 11.00000 0.09565 H2A 2 0.811056 0.018268 0.372983 11.00000 0.11212 H1A 2 0.583089 0.079394 0.305358 11.00000 0.09211 H4A 2 0.721240 0.377221 0.340890 11.00000 0.10497 H3A 2 0.778691 0.157634 0.271460 11.00000 0.10038 O1 4 0.656250 0.080778 0.329411 11.00000 0.05410 0.07757 = 0.04809 0.02174 0.01719 0.02831 O2 4 0.859480 0.053231 0.435369 11.00000 0.05597 0.08781 = 0.06868 0.02539 0.01551 0.03099 C25 1 0.794479 0.107573 0.492896 11.00000 0.04870 0.05598 = 0.05393 0.02214 0.01509 0.01172 C26 1 0.690720 0.123965 0.441069 11.00000 0.05062 0.05870 = 0.04704 0.02124 0.01517 0.01497 C27 1 0.629789 0.182780 0.502078 11.00000 0.07103 0.10271 = 0.05710 0.02564 0.02134 0.04219 AFIX 43 H27 2 0.561083 0.195611 0.467549 11.00000 -1.20000 AFIX 0 C30 1 0.834501 0.147892 0.605007 11.00000 0.06336 0.09039 = 0.06216 0.03333 0.00916 0.02228 AFIX 43 H30 2 0.904123 0.136860 0.640185 11.00000 -1.20000 AFIX 0 C28 1 0.669882 0.222623 0.613658 11.00000 0.09090 0.13010 = 0.05877 0.02219 0.03047 0.04915 AFIX 43 H28 2 0.628137 0.262005 0.654631 11.00000 -1.20000 AFIX 0 C29 1 0.771265 0.204446 0.664691 11.00000 0.08769 0.12017 = 0.05202 0.02383 0.01926 0.03354 AFIX 43 H29 2 0.797559 0.230544 0.740292 11.00000 -1.20000 AFIX 0 O5 4 0.752529 0.897695 0.217047 11.00000 0.04742 0.05887 = 0.07289 0.01523 0.02273 0.01959 C20 1 1.401792 1.077790 0.127509 11.00000 0.04453 0.04182 = 0.04480 0.01148 0.01700 0.01404 C18 1 1.527784 0.946323 0.044871 11.00000 0.03763 0.04666 = 0.04193 0.01494 0.01362 0.01554 AFIX 13 H18 2 1.614264 0.961750 0.079317 11.00000 -1.20000 AFIX 0 O6 4 0.935398 0.975698 0.149606 11.00000 0.05756 0.06507 = 0.10334 0.03751 0.03753 0.02455 C17 1 1.451755 0.847156 0.062580 11.00000 0.04541 0.04600 = 0.03845 0.01280 0.01805 0.01866 C19 1 1.498632 1.067315 0.075219 11.00000 0.03933 0.04295 = 0.04221 0.01313 0.01526 0.01284 AFIX 13 H19 2 1.573612 1.134189 0.121915 11.00000 -1.20000 AFIX 0 C37 1 0.904029 0.861893 0.141854 11.00000 0.04423 0.05874 = 0.05620 0.02085 0.01281 0.01834 C38 1 0.809445 0.818426 0.175185 11.00000 0.04445 0.05723 = 0.04487 0.01399 0.01023 0.01994 C15 1 1.260587 0.708810 0.031335 11.00000 0.05097 0.05707 = 0.06253 0.01415 0.02409 0.01103 AFIX 43 H15 2 1.176861 0.675596 -0.002280 11.00000 -1.20000 AFIX 0 C14 1 1.320581 0.668477 0.100982 11.00000 0.07266 0.05752 = 0.07090 0.02731 0.03758 0.01411 AFIX 43 H14 2 1.278263 0.607952 0.116026 11.00000 -1.20000 AFIX 0 C13 1 1.443758 0.718998 0.147818 11.00000 0.06948 0.06117 = 0.06321 0.03317 0.02980 0.02384 AFIX 43 H13 2 1.483846 0.690942 0.194703 11.00000 -1.20000 AFIX 0 C42 1 0.966851 0.788037 0.099824 11.00000 0.05822 0.07900 = 0.07518 0.02705 0.03023 0.03139 AFIX 43 H42 2 1.029789 0.816167 0.076579 11.00000 -1.20000 AFIX 0 C24 1 1.343222 1.076326 0.274594 11.00000 0.05894 0.08168 = 0.05077 0.01751 0.02775 0.01685 AFIX 43 H24 2 1.360672 1.072723 0.342418 11.00000 -1.20000 AFIX 0 C39 1 0.780715 0.703957 0.168675 11.00000 0.06495 0.05920 = 0.05661 0.02057 0.02010 0.01840 AFIX 43 H39 2 0.718350 0.675389 0.192329 11.00000 -1.20000 AFIX 0 C23 1 1.232293 1.083866 0.230123 11.00000 0.05685 0.08921 = 0.06704 0.01623 0.03619 0.02058 AFIX 43 H23 2 1.175853 1.085092 0.266605 11.00000 -1.20000 AFIX 0 C22 1 1.207209 1.089490 0.131332 11.00000 0.05667 0.10047 = 0.07570 0.03070 0.03222 0.03972 AFIX 43 H22 2 1.132980 1.095228 0.099138 11.00000 -1.20000 AFIX 0 C41 1 0.936221 0.673049 0.092428 11.00000 0.07050 0.07193 = 0.07500 0.01889 0.02516 0.03895 AFIX 43 H41 2 0.978276 0.623482 0.063710 11.00000 -1.20000 AFIX 0 C40 1 0.844396 0.631179 0.127004 11.00000 0.07827 0.05606 = 0.06977 0.02065 0.01782 0.02725 AFIX 43 H40 2 0.824731 0.553601 0.122488 11.00000 -1.20000 AFIX 0 O3 4 0.824182 0.148822 0.228959 11.00000 0.06638 0.05894 = 0.07833 0.02619 0.03434 0.02541 C8 1 1.315961 0.371648 0.490708 11.00000 0.04832 0.05350 = 0.04179 0.01665 0.01808 0.01174 C5 1 1.483522 0.425961 0.310624 11.00000 0.05839 0.03992 = 0.05185 0.01352 0.02624 0.01206 C7 1 1.399207 0.468355 0.475479 11.00000 0.04468 0.05394 = 0.05069 0.02502 0.02014 0.01730 AFIX 13 H7 2 1.352476 0.503741 0.435230 11.00000 -1.20000 AFIX 0 C31 1 0.884803 0.262035 0.243153 11.00000 0.04814 0.05963 = 0.05227 0.02428 0.01369 0.02256 C6 1 1.493533 0.431614 0.422691 11.00000 0.04890 0.04476 = 0.05220 0.01977 0.02382 0.01506 AFIX 13 H6 2 1.494283 0.353903 0.422251 11.00000 -1.20000 AFIX 0 O4 4 0.762143 0.332030 0.340006 11.00000 0.12838 0.09113 = 0.13993 0.06624 0.09884 0.06790 C36 1 0.973561 0.278118 0.196895 11.00000 0.05643 0.08404 = 0.08345 0.04107 0.03287 0.03341 AFIX 43 H36 2 0.992940 0.212860 0.157483 11.00000 -1.20000 AFIX 0 C32 1 0.853392 0.357301 0.299091 11.00000 0.07354 0.06694 = 0.07402 0.03163 0.03758 0.03285 C35 1 1.034127 0.390825 0.208692 11.00000 0.05554 0.10776 = 0.10020 0.06255 0.03244 0.02809 AFIX 43 H35 2 1.094438 0.401725 0.177414 11.00000 -1.20000 AFIX 0 C12 1 1.293325 0.217116 0.543505 11.00000 0.08301 0.06472 = 0.07148 0.03640 0.03143 0.01824 AFIX 43 H12 2 1.327592 0.169733 0.571135 11.00000 -1.20000 AFIX 0 C11 1 1.170240 0.192690 0.517522 11.00000 0.07630 0.07047 = 0.07632 0.02859 0.03573 -0.00102 AFIX 43 H11 2 1.122878 0.131009 0.528064 11.00000 -1.20000 AFIX 0 C10 1 1.118834 0.260633 0.475969 11.00000 0.05127 0.08267 = 0.07658 0.02691 0.02492 0.00271 AFIX 43 H10 2 1.035474 0.245635 0.456929 11.00000 -1.20000 AFIX 0 C3 1 1.370614 0.405257 0.135142 11.00000 0.10051 0.08635 = 0.05313 0.02388 0.02252 0.03384 AFIX 43 H3 2 1.298328 0.396476 0.085678 11.00000 -1.20000 AFIX 0 C1 1 1.574434 0.417287 0.180243 11.00000 0.10319 0.06631 = 0.07527 0.02252 0.05986 0.02493 AFIX 43 H1 2 1.643208 0.418289 0.159602 11.00000 -1.20000 AFIX 0 C2 1 1.471603 0.408208 0.105909 11.00000 0.12781 0.07077 = 0.05105 0.02126 0.03771 0.02911 AFIX 43 H2 2 1.470829 0.404159 0.037138 11.00000 -1.20000 AFIX 0 C34 1 1.005427 0.486087 0.266228 11.00000 0.08402 0.07593 = 0.11282 0.04991 0.03088 0.01491 AFIX 43 H34 2 1.047345 0.562553 0.275870 11.00000 -1.20000 AFIX 0 C33 1 0.914313 0.468922 0.310029 11.00000 0.12109 0.06356 = 0.11079 0.03591 0.06076 0.03607 AFIX 43 H33 2 0.893598 0.534021 0.347702 11.00000 -1.20000 AFIX 0 HKLF 4 REM 3(cat).(2,2'-tpcb) in P-1 REM R1 = 0.0512 for 4235 Fo > 4sig(Fo) and 0.0779 for all 5711 data REM 493 parameters refined using 6 restraints END WGHT 0.1084 0.0953 REM Highest difference peak 0.294, deepest hole -0.425, 1-sigma level 0.100 Q1 1 0.6524 0.1424 0.6209 11.00000 0.05 0.29 Q2 1 0.5963 0.0979 0.5003 11.00000 0.05 0.23 Q3 1 0.7370 0.1199 0.6494 11.00000 0.05 0.23 Q4 1 1.0000 0.5000 0.0000 10.50000 0.05 0.22 Q5 1 1.0013 0.5953 -0.0295 11.00000 0.05 0.22 Q6 1 1.0328 0.5174 0.0840 11.00000 0.05 0.21 Q7 1 1.0204 0.6619 0.0326 11.00000 0.05 0.21 Q8 1 0.9075 0.5805 -0.0428 11.00000 0.05 0.21 Q9 1 0.9760 0.5779 0.0354 11.00000 0.05 0.21 Q10 1 1.0543 0.5371 -0.0837 11.00000 0.05 0.21 Q11 1 0.5848 0.2069 0.6543 11.00000 0.05 0.21 Q12 1 1.0701 0.3813 0.0929 11.00000 0.05 0.20 Q13 1 0.9789 0.5028 0.3880 11.00000 0.05 0.20 Q14 1 1.0227 0.6048 0.1300 11.00000 0.05 0.20 Q15 1 0.8448 0.3002 0.7666 11.00000 0.05 0.20 Q16 1 1.0537 0.6685 0.1228 11.00000 0.05 0.20 Q17 1 1.1579 0.5876 0.2127 11.00000 0.05 0.20 Q18 1 1.0918 0.6039 0.0568 11.00000 0.05 0.20 Q19 1 0.6014 0.0387 0.5314 11.00000 0.05 0.20 Q20 1 0.8996 0.4855 0.0180 11.00000 0.05 0.20 ; _shelx_res_checksum 35709 _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, -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 N1 N 1.50990(16) 0.80656(16) 0.13000(14) 0.0493(5) Uani 1 1 d . N2 N 1.42774(16) 1.07386(17) 0.22587(14) 0.0548(5) Uani 1 1 d . C16 C 1.3264(2) 0.7992(2) 0.01210(18) 0.0508(5) Uani 1 1 d . H16 H 1.2873 0.8281 -0.0345 0.061 Uiso 1 1 calc R C21 C 1.2922(2) 1.0867(2) 0.0791(2) 0.0623(7) Uani 1 1 d . H21 H 1.2758 1.0907 0.0115 0.075 Uiso 1 1 calc R N4 N 1.36731(18) 0.30528(18) 0.53146(16) 0.0594(5) Uani 1 1 d . C4 C 1.3764(3) 0.4154(2) 0.2385(2) 0.0684(7) Uani 1 1 d . H4 H 1.3083 0.4151 0.2600 0.082 Uiso 1 1 calc R N3 N 1.58253(19) 0.42490(18) 0.28178(16) 0.0622(5) Uani 1 1 d . C9 C 1.1921(2) 0.3518(2) 0.46256(19) 0.0609(6) Uani 1 1 d . H9 H 1.1588 0.3997 0.4349 0.073 Uiso 1 1 calc R H6A H 0.890(3) 1.016(3) 0.177(3) 0.106(11) Uiso 1 1 d D H5 H 0.6753(17) 0.868(3) 0.197(3) 0.096(11) Uiso 1 1 d D H2A H 0.811(3) 0.018(3) 0.3730(18) 0.112(13) Uiso 1 1 d D H1A H 0.5831(18) 0.079(3) 0.305(2) 0.092(10) Uiso 1 1 d D H4A H 0.721(3) 0.377(3) 0.341(3) 0.105(12) Uiso 1 1 d D H3A H 0.779(3) 0.158(3) 0.271(2) 0.100(11) Uiso 1 1 d D O1 O 0.65625(15) 0.08078(15) 0.32941(12) 0.0599(4) Uani 1 1 d D O2 O 0.85948(16) 0.05323(18) 0.43537(16) 0.0724(5) Uani 1 1 d D C25 C 0.7945(2) 0.1076(2) 0.49290(18) 0.0544(6) Uani 1 1 d . C26 C 0.6907(2) 0.1240(2) 0.44107(18) 0.0530(6) Uani 1 1 d . C27 C 0.6298(3) 0.1828(3) 0.5021(2) 0.0766(8) Uani 1 1 d . H27 H 0.5611 0.1956 0.4675 0.092 Uiso 1 1 calc R C30 C 0.8345(3) 0.1479(3) 0.6050(2) 0.0742(8) Uani 1 1 d . H30 H 0.9041 0.1369 0.6402 0.089 Uiso 1 1 calc R C28 C 0.6699(3) 0.2226(3) 0.6137(2) 0.0947(10) Uani 1 1 d . H28 H 0.6281 0.2620 0.6546 0.114 Uiso 1 1 calc R C29 C 0.7713(3) 0.2044(3) 0.6647(2) 0.0909(10) Uani 1 1 d . H29 H 0.7976 0.2305 0.7403 0.109 Uiso 1 1 calc R O5 O 0.75253(16) 0.89770(15) 0.21705(14) 0.0623(5) Uani 1 1 d D C20 C 1.40179(19) 1.07779(18) 0.12751(17) 0.0452(5) Uani 1 1 d . C18 C 1.52778(19) 0.94632(18) 0.04487(16) 0.0427(5) Uani 1 1 d . H18 H 1.6143 0.9618 0.0793 0.051 Uiso 1 1 calc R O6 O 0.93540(16) 0.97570(16) 0.14961(17) 0.0717(5) Uani 1 1 d D C17 C 1.45176(19) 0.84716(18) 0.06258(16) 0.0432(5) Uani 1 1 d . C19 C 1.49863(18) 1.06732(18) 0.07522(16) 0.0426(5) Uani 1 1 d . H19 H 1.5736 1.1342 0.1219 0.051 Uiso 1 1 calc R C37 C 0.9040(2) 0.8619(2) 0.14185(18) 0.0543(6) Uani 1 1 d . C38 C 0.8094(2) 0.8184(2) 0.17518(17) 0.0512(6) Uani 1 1 d . C15 C 1.2606(2) 0.7088(2) 0.0313(2) 0.0601(6) Uani 1 1 d . H15 H 1.1769 0.6756 -0.0023 0.072 Uiso 1 1 calc R C14 C 1.3206(3) 0.6685(2) 0.1010(2) 0.0656(7) Uani 1 1 d . H14 H 1.2783 0.6080 0.1160 0.079 Uiso 1 1 calc R C13 C 1.4438(2) 0.7190(2) 0.1478(2) 0.0606(6) Uani 1 1 d . H13 H 1.4838 0.6909 0.1947 0.073 Uiso 1 1 calc R C42 C 0.9669(2) 0.7880(3) 0.0998(2) 0.0691(7) Uani 1 1 d . H42 H 1.0298 0.8162 0.0766 0.083 Uiso 1 1 calc R C24 C 1.3432(2) 1.0763(2) 0.2746(2) 0.0660(7) Uani 1 1 d . H24 H 1.3607 1.0727 0.3424 0.079 Uiso 1 1 calc R C39 C 0.7807(2) 0.7040(2) 0.16868(19) 0.0616(6) Uani 1 1 d . H39 H 0.7184 0.6754 0.1923 0.074 Uiso 1 1 calc R C23 C 1.2323(2) 1.0839(3) 0.2301(2) 0.0734(8) Uani 1 1 d . H23 H 1.1759 1.0851 0.2666 0.088 Uiso 1 1 calc R C22 C 1.2072(2) 1.0895(3) 0.1313(2) 0.0748(8) Uani 1 1 d . H22 H 1.1330 1.0952 0.0991 0.090 Uiso 1 1 calc R C41 C 0.9362(3) 0.6730(3) 0.0924(2) 0.0727(8) Uani 1 1 d . H41 H 0.9783 0.6235 0.0637 0.087 Uiso 1 1 calc R C40 C 0.8444(3) 0.6312(2) 0.1270(2) 0.0699(7) Uani 1 1 d . H40 H 0.8247 0.5536 0.1225 0.084 Uiso 1 1 calc R O3 O 0.82418(16) 0.14882(15) 0.22896(15) 0.0657(5) Uani 1 1 d D C8 C 1.3160(2) 0.3716(2) 0.49071(17) 0.0491(5) Uani 1 1 d . C5 C 1.4835(2) 0.42596(19) 0.31062(18) 0.0509(6) Uani 1 1 d . C7 C 1.39921(19) 0.4684(2) 0.47548(17) 0.0478(5) Uani 1 1 d . H7 H 1.3525 0.5037 0.4352 0.057 Uiso 1 1 calc R C31 C 0.8848(2) 0.2620(2) 0.24315(18) 0.0527(6) Uani 1 1 d . C6 C 1.49353(19) 0.43161(19) 0.42269(17) 0.0474(5) Uani 1 1 d . H6 H 1.4943 0.3539 0.4223 0.057 Uiso 1 1 calc R O4 O 0.7621(2) 0.3320(2) 0.3400(2) 0.0985(8) Uani 1 1 d D C36 C 0.9736(2) 0.2781(3) 0.1969(2) 0.0691(7) Uani 1 1 d . H36 H 0.9929 0.2129 0.1575 0.083 Uiso 1 1 calc R C32 C 0.8534(2) 0.3573(2) 0.2991(2) 0.0666(7) Uani 1 1 d . C35 C 1.0341(2) 0.3908(3) 0.2087(3) 0.0807(9) Uani 1 1 d . H35 H 1.0944 0.4017 0.1774 0.097 Uiso 1 1 calc R C12 C 1.2933(3) 0.2171(2) 0.5435(2) 0.0707(7) Uani 1 1 d . H12 H 1.3276 0.1697 0.5711 0.085 Uiso 1 1 calc R C11 C 1.1702(3) 0.1927(3) 0.5175(2) 0.0775(8) Uani 1 1 d . H11 H 1.1229 0.1310 0.5281 0.093 Uiso 1 1 calc R C10 C 1.1188(2) 0.2606(3) 0.4760(2) 0.0747(8) Uani 1 1 d . H10 H 1.0355 0.2456 0.4569 0.090 Uiso 1 1 calc R C3 C 1.3706(3) 0.4053(3) 0.1351(2) 0.0814(8) Uani 1 1 d . H3 H 1.2983 0.3965 0.0857 0.098 Uiso 1 1 calc R C1 C 1.5744(3) 0.4173(2) 0.1802(3) 0.0784(8) Uani 1 1 d . H1 H 1.6432 0.4183 0.1596 0.094 Uiso 1 1 calc R C2 C 1.4716(4) 0.4082(3) 0.1059(2) 0.0835(9) Uani 1 1 d . H2 H 1.4708 0.4042 0.0371 0.100 Uiso 1 1 calc R C34 C 1.0054(3) 0.4861(3) 0.2662(3) 0.0902(9) Uani 1 1 d . H34 H 1.0473 0.5626 0.2759 0.108 Uiso 1 1 calc R C33 C 0.9143(3) 0.4689(3) 0.3100(3) 0.0933(10) Uani 1 1 d . H33 H 0.8936 0.5340 0.3477 0.112 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 N1 0.0530(11) 0.0525(11) 0.0479(10) 0.0208(9) 0.0218(9) 0.0220(9) N2 0.0509(11) 0.0661(12) 0.0453(10) 0.0169(9) 0.0221(9) 0.0190(9) C16 0.0456(13) 0.0512(13) 0.0509(12) 0.0163(10) 0.0163(10) 0.0147(11) C21 0.0568(15) 0.0844(17) 0.0600(14) 0.0318(13) 0.0275(12) 0.0378(13) N4 0.0591(12) 0.0599(12) 0.0621(12) 0.0296(10) 0.0226(10) 0.0155(10) C4 0.0681(17) 0.0781(18) 0.0536(15) 0.0212(13) 0.0212(13) 0.0223(14) N3 0.0697(14) 0.0576(12) 0.0618(13) 0.0179(10) 0.0381(11) 0.0192(10) C9 0.0446(14) 0.0738(16) 0.0594(14) 0.0270(12) 0.0169(11) 0.0116(12) O1 0.0541(11) 0.0776(11) 0.0481(9) 0.0217(8) 0.0172(8) 0.0283(9) O2 0.0560(11) 0.0878(13) 0.0687(12) 0.0254(10) 0.0155(10) 0.0310(10) C25 0.0487(13) 0.0560(13) 0.0539(13) 0.0221(11) 0.0151(11) 0.0117(11) C26 0.0506(13) 0.0587(14) 0.0470(13) 0.0212(10) 0.0152(11) 0.0150(11) C27 0.0710(18) 0.103(2) 0.0571(16) 0.0256(15) 0.0213(13) 0.0422(16) C30 0.0634(17) 0.090(2) 0.0622(16) 0.0333(15) 0.0092(14) 0.0223(15) C28 0.091(2) 0.130(3) 0.0588(17) 0.0222(17) 0.0305(16) 0.049(2) C29 0.088(2) 0.120(3) 0.0520(16) 0.0238(16) 0.0193(16) 0.034(2) O5 0.0474(10) 0.0589(10) 0.0729(11) 0.0152(8) 0.0227(9) 0.0196(9) C20 0.0445(12) 0.0418(11) 0.0448(12) 0.0115(9) 0.0170(10) 0.0140(9) C18 0.0376(11) 0.0467(12) 0.0419(11) 0.0149(9) 0.0136(9) 0.0155(9) O6 0.0576(11) 0.0651(12) 0.1033(14) 0.0375(10) 0.0375(10) 0.0246(9) C17 0.0454(12) 0.0460(12) 0.0384(10) 0.0128(9) 0.0181(9) 0.0187(10) C19 0.0393(11) 0.0430(11) 0.0422(11) 0.0131(9) 0.0153(9) 0.0128(9) C37 0.0442(13) 0.0587(14) 0.0562(13) 0.0208(11) 0.0128(11) 0.0183(11) C38 0.0444(13) 0.0572(14) 0.0449(12) 0.0140(10) 0.0102(10) 0.0199(11) C15 0.0510(14) 0.0571(14) 0.0625(15) 0.0142(12) 0.0241(12) 0.0110(12) C14 0.0727(18) 0.0575(14) 0.0709(16) 0.0273(13) 0.0376(14) 0.0141(13) C13 0.0695(17) 0.0612(15) 0.0632(15) 0.0332(12) 0.0298(13) 0.0238(13) C42 0.0582(16) 0.0790(19) 0.0752(17) 0.0271(14) 0.0302(13) 0.0314(14) C24 0.0589(16) 0.0817(18) 0.0508(13) 0.0175(12) 0.0278(12) 0.0169(14) C39 0.0650(16) 0.0592(15) 0.0566(14) 0.0206(12) 0.0201(12) 0.0184(12) C23 0.0568(16) 0.0892(19) 0.0670(17) 0.0162(14) 0.0362(14) 0.0206(14) C22 0.0567(16) 0.100(2) 0.0757(18) 0.0307(15) 0.0322(14) 0.0397(15) C41 0.0705(18) 0.0719(18) 0.0750(18) 0.0189(14) 0.0252(15) 0.0390(15) C40 0.0783(19) 0.0561(15) 0.0698(16) 0.0207(13) 0.0178(14) 0.0272(14) O3 0.0664(11) 0.0589(10) 0.0783(12) 0.0262(9) 0.0343(10) 0.0254(9) C8 0.0483(13) 0.0535(13) 0.0418(11) 0.0166(10) 0.0181(10) 0.0117(11) C5 0.0584(14) 0.0399(11) 0.0519(13) 0.0135(10) 0.0262(11) 0.0121(10) C7 0.0447(12) 0.0539(13) 0.0507(12) 0.0250(10) 0.0201(10) 0.0173(10) C31 0.0481(13) 0.0596(15) 0.0523(13) 0.0243(11) 0.0137(11) 0.0226(11) C6 0.0489(13) 0.0448(12) 0.0522(12) 0.0198(10) 0.0238(10) 0.0151(10) O4 0.1284(19) 0.0911(15) 0.140(2) 0.0662(15) 0.0988(17) 0.0679(15) C36 0.0564(15) 0.0840(19) 0.0834(18) 0.0411(15) 0.0329(14) 0.0334(14) C32 0.0735(17) 0.0669(17) 0.0740(16) 0.0316(14) 0.0376(14) 0.0329(14) C35 0.0555(17) 0.108(3) 0.100(2) 0.063(2) 0.0324(16) 0.0281(17) C12 0.083(2) 0.0647(16) 0.0715(17) 0.0364(13) 0.0314(15) 0.0182(15) C11 0.076(2) 0.0705(18) 0.0763(18) 0.0286(15) 0.0357(15) -0.0010(15) C10 0.0513(15) 0.0827(19) 0.0766(18) 0.0269(15) 0.0249(13) 0.0027(14) C3 0.101(2) 0.086(2) 0.0531(16) 0.0239(14) 0.0225(16) 0.0338(17) C1 0.103(2) 0.0663(17) 0.0753(19) 0.0225(14) 0.0599(19) 0.0249(16) C2 0.128(3) 0.0708(18) 0.0510(16) 0.0213(13) 0.0377(19) 0.0291(18) C34 0.084(2) 0.076(2) 0.113(2) 0.0499(19) 0.031(2) 0.0149(17) C33 0.121(3) 0.0636(18) 0.111(3) 0.0359(17) 0.061(2) 0.0361(18) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C13 N1 C17 118.0(2) . . C24 N2 C20 118.0(2) . . C15 C16 C17 119.7(2) . . C22 C21 C20 119.7(2) . . C8 N4 C12 117.0(2) . . C3 C4 C5 120.0(3) . . C5 N3 C1 117.0(2) . . C10 C9 C8 119.4(3) . . O2 C25 C26 121.3(2) . . O2 C25 C30 118.9(2) . . C30 C25 C26 119.8(2) . . O1 C26 C25 116.4(2) . . O1 C26 C27 123.9(2) . . C27 C26 C25 119.7(2) . . C28 C27 C26 120.3(3) . . C29 C30 C25 119.8(3) . . C29 C28 C27 120.0(3) . . C28 C29 C30 120.4(3) . . N2 C20 C21 120.97(19) . . N2 C20 C19 114.76(18) . . C21 C20 C19 124.2(2) . . C17 C18 C19 118.09(16) . . C17 C18 C19 116.52(16) . 2_875 C19 C18 C19 89.21(14) 2_875 . N1 C17 C16 121.1(2) . . N1 C17 C18 117.04(18) . . C16 C17 C18 121.90(19) . . C20 C19 C18 119.51(17) . 2_875 C20 C19 C18 117.27(17) . . C18 C19 C18 90.79(14) 2_875 . O6 C37 C38 120.9(2) . . O6 C37 C42 119.7(2) . . C42 C37 C38 119.4(2) . . O5 C38 C37 115.9(2) . . C39 C38 O5 124.1(2) . . C39 C38 C37 120.0(2) . . C14 C15 C16 118.8(2) . . C13 C14 C15 118.7(2) . . N1 C13 C14 123.7(2) . . C41 C42 C37 120.0(3) . . N2 C24 C23 123.6(2) . . C38 C39 C40 120.0(3) . . C22 C23 C24 118.1(2) . . C23 C22 C21 119.6(3) . . C40 C41 C42 120.4(2) . . C41 C40 C39 120.1(3) . . N4 C8 C9 122.1(2) . . N4 C8 C7 116.56(19) . . C9 C8 C7 121.3(2) . . C4 C5 C6 122.3(2) . . N3 C5 C4 121.5(2) . . N3 C5 C6 116.1(2) . . C8 C7 C6 119.03(17) . 2_866 C8 C7 C6 115.43(18) . . C6 C7 C6 88.90(15) . 2_866 C36 C31 O3 119.2(2) . . C36 C31 C32 120.4(2) . . C32 C31 O3 120.3(2) . . C5 C6 C7 119.91(18) . 2_866 C5 C6 C7 119.51(18) . . C7 C6 C7 91.10(15) . 2_866 C31 C36 C35 120.1(3) . . O4 C32 C31 116.1(2) . . O4 C32 C33 125.0(3) . . C33 C32 C31 118.8(3) . . C34 C35 C36 119.8(3) . . N4 C12 C11 123.9(3) . . C10 C11 C12 118.6(3) . . C11 C10 C9 119.0(3) . . C2 C3 C4 119.2(3) . . N3 C1 C2 124.1(3) . . C3 C2 C1 118.2(3) . . C35 C34 C33 119.8(3) . . C32 C33 C34 121.1(3) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 C17 1.342(3) . N1 C13 1.338(3) . N2 C20 1.342(3) . N2 C24 1.337(3) . C16 C17 1.392(3) . C16 C15 1.374(3) . C21 C20 1.379(3) . C21 C22 1.374(4) . N4 C8 1.338(3) . N4 C12 1.342(3) . C4 C5 1.381(3) . C4 C3 1.371(4) . N3 C5 1.336(3) . N3 C1 1.350(4) . C9 C8 1.387(3) . C9 C10 1.376(4) . O1 C26 1.370(3) . O2 C25 1.362(3) . C25 C26 1.383(3) . C25 C30 1.377(3) . C26 C27 1.374(3) . C27 C28 1.371(4) . C30 C29 1.373(4) . C28 C29 1.368(4) . O5 C38 1.375(3) . C20 C19 1.506(3) . C18 C17 1.501(3) . C18 C19 1.554(3) 2_875 C18 C19 1.580(3) . O6 C37 1.359(3) . C19 C18 1.554(3) 2_875 C37 C38 1.388(3) . C37 C42 1.384(3) . C38 C39 1.373(3) . C15 C14 1.372(4) . C14 C13 1.366(4) . C42 C41 1.375(4) . C24 C23 1.370(4) . C39 C40 1.382(4) . C23 C22 1.357(4) . C41 C40 1.366(4) . O3 C31 1.373(3) . C8 C7 1.500(3) . C5 C6 1.498(3) . C7 C6 1.550(3) . C7 C6 1.569(3) 2_866 C31 C36 1.371(3) . C31 C32 1.372(3) . C6 C7 1.569(3) 2_866 O4 C32 1.365(3) . C36 C35 1.378(4) . C32 C33 1.372(4) . C35 C34 1.360(4) . C12 C11 1.371(4) . C11 C10 1.361(4) . C3 C2 1.357(4) . C1 C2 1.366(4) . C34 C33 1.374(4) . 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 O6 H6A O3 0.878(18) 2.00(2) 2.843(2) 161(3) 1_565 O2 H2A O5 0.819(18) 2.01(2) 2.766(3) 153(3) 1_545 O1 H1A N2 0.858(18) 1.906(19) 2.752(2) 169(3) 1_445 O4 H4A N3 0.830(18) 1.99(2) 2.763(3) 155(3) 1_455 O3 H3A O1 0.884(18) 2.04(2) 2.830(2) 149(3) .