#------------------------------------------------------------------------------ #$Date: 2021-10-06 16:48:30 +0300 (Wed, 06 Oct 2021) $ #$Revision: 269621 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/89/7128943.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_7128943 loop_ _publ_author_name 'Yan, Hang' 'Jia, Shi-Kun' 'Geng, Yu-Huan' 'Han, Jiao-Jiao' 'Hua, Yuan-Zhao' 'Wang, Min-Can' _publ_section_title ; Dinuclear zinc-catalyzed asymmetric Friedel-Crafts alkylation/cyclization of 3-aminophenols with \a,\a-dicyanoolefins. ; _journal_issue 77 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 9854 _journal_page_last 9857 _journal_paper_doi 10.1039/d1cc04177k _journal_volume 57 _journal_year 2021 _chemical_formula_sum 'C31 H24 N4 O2' _chemical_formula_weight 484.54 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-01-16 deposited with the CCDC. 2021-08-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.4348(4) _cell_length_b 10.8834(5) _cell_length_c 24.5503(9) _cell_measurement_temperature 293(2) _cell_volume 2520.89(18) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_unetI/netI 0.0270 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 22349 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 67.077 _diffrn_reflns_theta_max 67.077 _diffrn_reflns_theta_min 3.601 _exptl_absorpt_coefficient_mu 0.651 _exptl_crystal_density_diffrn 1.277 _exptl_crystal_F_000 1016 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.139 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.044 _refine_ls_abs_structure_details ; Flack x determined using 1568 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.19(15) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 346 _refine_ls_number_reflns 4490 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0404 _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^)+(0.0582P)^2^+0.1303P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0993 _refine_ls_wR_factor_ref 0.1049 _reflns_Friedel_coverage 0.748 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 3996 _reflns_number_total 4490 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc04177k2.cif _cod_data_source_block 202010225 _cod_depositor_comments 'Adding full bibliography for 7128943.cif.' _cod_database_code 7128943 _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. ; _shelx_estimated_absorpt_t_min 0.909 _shelx_estimated_absorpt_t_max 0.938 _shelx_res_file ; 202010225.res created by SHELXL-2014/7 TITL 202010225 in P212121 #19 REM reset to P212121 #19 CELL 1.54184 9.434752 10.883443 24.550288 90 90 90 ZERR 4 0.000377 0.000513 0.000901 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 UNIT 124 96 16 8 EQIV $1 1-X,-0.5+Y,0.5-Z DFIX 0.87 H1 N1 L.S. 4 0 0 PLAN 20 SIZE 0.15 0.12 0.1 MPLA C1 C2 C3 C4 C5 C6 C7 C8 MPLA C8 C9 C10 C11 C12 C13 C14 C15 C16 MPLA C19 C20 C21 C22 C23 C24 MPLA C26 C27 C28 C29 C30 C31 HTAB N2 O1_$1 HTAB N2 N3 htab BOND $h conf fmap 2 ACTA REM REM REM WGHT 0.058200 0.130300 FVAR 5.88401 O1 4 0.334890 0.491579 0.181736 11.00000 0.06739 0.08603 = 0.04861 0.00293 0.00675 -0.02599 N1 3 0.097707 0.471157 0.166124 11.00000 0.06907 0.06127 = 0.05059 0.01710 -0.00987 -0.00448 H1 2 0.092197 0.517067 0.138998 11.00000 0.07705 C1 1 -0.161409 0.419640 0.178468 11.00000 0.06220 0.07533 = 0.08231 0.00025 -0.02693 0.01178 AFIX 43 H1A 2 -0.193961 0.468373 0.149976 11.00000 -1.20000 AFIX 0 O2 4 0.434063 0.255581 0.298477 11.00000 0.04225 0.05802 = 0.05610 -0.01843 -0.01063 0.00973 N2 3 0.465261 0.097794 0.242784 11.00000 0.05462 0.06111 = 0.06864 -0.02322 -0.01229 0.01441 H2A 2 0.520373 0.073341 0.267783 11.00000 0.07050 H2B 2 0.431786 0.055829 0.213797 11.00000 0.08541 C2 1 -0.254469 0.352827 0.210266 11.00000 0.04160 0.08782 = 0.10013 -0.02303 -0.01133 0.00135 AFIX 43 H2 2 -0.351113 0.357285 0.203079 11.00000 -1.20000 AFIX 0 N3 3 0.192243 0.086437 0.149116 11.00000 0.11303 0.08729 = 0.06867 -0.03024 -0.02782 0.00187 C3 1 -0.207849 0.280426 0.251986 11.00000 0.04840 0.07522 = 0.08033 -0.01743 0.00665 -0.01506 AFIX 43 H3 2 -0.272793 0.236769 0.272903 11.00000 -1.20000 AFIX 0 N4 3 0.387008 0.551940 0.440013 11.00000 0.06579 0.05635 = 0.04831 -0.01567 -0.00967 0.00166 C4 1 -0.064430 0.271583 0.263355 11.00000 0.05433 0.05287 = 0.05341 -0.00383 0.00033 -0.00973 AFIX 43 H4 2 -0.032558 0.221481 0.291492 11.00000 -1.20000 AFIX 0 C5 1 0.030196 0.337791 0.232530 11.00000 0.04261 0.04310 = 0.04300 -0.00588 -0.00413 -0.00055 C6 1 -0.018393 0.411838 0.190300 11.00000 0.05399 0.05140 = 0.05487 -0.00069 -0.01106 0.00110 C7 1 0.221059 0.445861 0.191906 11.00000 0.05601 0.05240 = 0.03645 -0.00329 0.00010 -0.00908 C8 1 0.189413 0.349943 0.237479 11.00000 0.04264 0.04436 = 0.03715 -0.00092 -0.00064 -0.00192 C9 1 0.268066 0.230995 0.226058 11.00000 0.04574 0.05046 = 0.04075 -0.00678 -0.00284 -0.00108 C10 1 0.383991 0.195249 0.254300 11.00000 0.04072 0.04743 = 0.04889 -0.00995 0.00153 -0.00244 C11 1 0.355356 0.354694 0.318569 11.00000 0.03939 0.03912 = 0.04128 -0.00259 0.00098 -0.00277 C12 1 0.238287 0.400493 0.291801 11.00000 0.04105 0.04002 = 0.03602 0.00161 0.00125 -0.00254 C13 1 0.170535 0.498766 0.317041 11.00000 0.05226 0.04546 = 0.04290 0.00261 -0.00393 0.00645 AFIX 43 H13 2 0.090048 0.531805 0.300802 11.00000 -1.20000 AFIX 0 C14 1 0.218253 0.548940 0.365192 11.00000 0.06212 0.04429 = 0.04714 -0.00704 -0.00080 0.00918 AFIX 43 H14 2 0.170237 0.615456 0.380192 11.00000 -1.20000 AFIX 0 C15 1 0.337498 0.501958 0.392046 11.00000 0.05198 0.04324 = 0.03954 -0.00254 -0.00068 -0.00781 C16 1 0.405052 0.400714 0.367525 11.00000 0.04183 0.04718 = 0.04439 -0.00141 -0.00567 -0.00224 AFIX 43 H16 2 0.483155 0.364731 0.384247 11.00000 -1.20000 AFIX 0 C17 1 0.224315 0.153328 0.182973 11.00000 0.05897 0.06198 = 0.05230 -0.01063 -0.00965 0.00434 C18 1 0.306857 0.641428 0.471919 11.00000 0.06737 0.06071 = 0.04163 -0.00920 0.00073 -0.00601 AFIX 23 H18A 2 0.299949 0.612364 0.509175 11.00000 -1.20000 H18B 2 0.211452 0.646757 0.457385 11.00000 -1.20000 AFIX 0 C19 1 0.371754 0.768064 0.472068 11.00000 0.05188 0.05440 = 0.04250 -0.00348 -0.00147 0.00278 C20 1 0.432162 0.821219 0.426400 11.00000 0.09397 0.07814 = 0.04771 -0.00188 0.01164 -0.00375 AFIX 43 H20 2 0.438067 0.777166 0.394020 11.00000 -1.20000 AFIX 0 C21 1 0.484089 0.940918 0.429093 11.00000 0.08496 0.08536 = 0.08040 0.02536 0.02169 -0.00602 AFIX 43 H21 2 0.524333 0.976831 0.398395 11.00000 -1.20000 AFIX 0 C22 1 0.476140 1.005532 0.476504 11.00000 0.06545 0.05753 = 0.09757 -0.00230 0.00316 -0.00260 AFIX 43 H22 2 0.508609 1.086168 0.477712 11.00000 -1.20000 AFIX 0 C23 1 0.421432 0.953339 0.521794 11.00000 0.08542 0.05893 = 0.07266 -0.01662 0.00343 -0.00291 AFIX 43 H23 2 0.419149 0.997078 0.554325 11.00000 -1.20000 AFIX 0 C24 1 0.368896 0.834977 0.519744 11.00000 0.06624 0.05494 = 0.05062 -0.00914 0.00421 0.00003 AFIX 43 H24 2 0.330962 0.799826 0.551043 11.00000 -1.20000 AFIX 0 C25 1 0.513066 0.507123 0.467095 11.00000 0.05818 0.07126 = 0.05260 -0.01861 -0.01067 -0.00875 AFIX 23 H25A 2 0.561083 0.576261 0.483863 11.00000 -1.20000 H25B 2 0.576348 0.473161 0.439837 11.00000 -1.20000 AFIX 0 C26 1 0.487195 0.410241 0.510358 11.00000 0.06718 0.05978 = 0.04702 -0.01659 -0.01115 0.01069 C27 1 0.596139 0.373042 0.544252 11.00000 0.06838 0.11153 = 0.05880 -0.01661 -0.01039 0.02562 AFIX 43 H27 2 0.685992 0.406947 0.540164 11.00000 -1.20000 AFIX 0 C28 1 0.572083 0.284528 0.584756 11.00000 0.11597 0.09861 = 0.05809 -0.00811 -0.02116 0.04815 AFIX 43 H28 2 0.646545 0.259284 0.606913 11.00000 -1.20000 AFIX 0 C29 1 0.441586 0.235536 0.591895 11.00000 0.14313 0.06253 = 0.05702 -0.01020 -0.00861 0.01123 AFIX 43 H29 2 0.426047 0.177972 0.619247 11.00000 -1.20000 AFIX 0 C30 1 0.332664 0.271071 0.558698 11.00000 0.11098 0.06277 = 0.07749 -0.00304 -0.00793 -0.01429 AFIX 43 H30 2 0.242953 0.237217 0.563299 11.00000 -1.20000 AFIX 0 C31 1 0.355878 0.357669 0.518120 11.00000 0.07781 0.05916 = 0.07321 -0.00333 -0.01919 -0.00668 AFIX 43 H31 2 0.281068 0.380708 0.495667 11.00000 -1.20000 AFIX 0 HKLF 4 REM 202010225 in P212121 #19 REM R1 = 0.0404 for 3996 Fo > 4sig(Fo) and 0.0472 for all 4490 data REM 346 parameters refined using 1 restraints END WGHT 0.0582 0.1303 REM Instructions for potential hydrogen bonds HTAB N2 O1_$1 REM Highest difference peak 0.139, deepest hole -0.209, 1-sigma level 0.044 Q1 1 -0.0795 0.3858 0.1130 11.00000 0.05 0.14 Q2 1 0.6894 0.1396 0.6293 11.00000 0.05 0.12 Q3 1 0.6579 0.5382 0.4085 11.00000 0.05 0.12 Q4 1 0.6360 0.4820 0.3931 11.00000 0.05 0.12 Q5 1 0.5625 1.1203 0.4096 11.00000 0.05 0.11 Q6 1 0.2622 0.3400 0.3135 11.00000 0.05 0.11 Q7 1 -0.1545 0.4773 0.0916 11.00000 0.05 0.11 Q8 1 -0.1696 0.4366 0.1317 11.00000 0.05 0.11 Q9 1 0.5665 0.5564 0.3938 11.00000 0.05 0.11 Q10 1 0.6771 0.4240 0.3727 11.00000 0.05 0.11 Q11 1 0.5792 1.0260 0.5845 11.00000 0.05 0.10 Q12 1 0.0599 0.1757 0.3154 11.00000 0.05 0.10 Q13 1 0.6106 0.4817 0.4393 11.00000 0.05 0.10 Q14 1 0.7714 0.5337 0.5687 11.00000 0.05 0.10 Q15 1 0.5024 0.8898 0.3547 11.00000 0.05 0.10 Q16 1 0.4065 0.1511 0.1381 11.00000 0.05 0.10 Q17 1 0.0995 0.2309 0.3200 11.00000 0.05 0.10 Q18 1 0.6361 0.8633 0.3663 11.00000 0.05 0.10 Q19 1 0.7615 0.2353 0.6273 11.00000 0.05 0.10 Q20 1 0.4021 0.7127 0.3738 11.00000 0.05 0.10 ; _shelx_res_checksum 67768 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3349(2) 0.4916(2) 0.18174(8) 0.0673(6) Uani 1 1 d . . . . . N1 N 0.0977(3) 0.4712(2) 0.16612(10) 0.0603(7) Uani 1 1 d D . . . . H1 H 0.092(4) 0.517(3) 0.1390(12) 0.077(12) Uiso 1 1 d D . . . . C1 C -0.1614(4) 0.4196(4) 0.17847(15) 0.0733(9) Uani 1 1 d . . . . . H1A H -0.1940 0.4684 0.1500 0.088 Uiso 1 1 calc R U . . . O2 O 0.43406(19) 0.25558(18) 0.29848(8) 0.0521(5) Uani 1 1 d . . . . . N2 N 0.4653(3) 0.0978(3) 0.24278(12) 0.0615(7) Uani 1 1 d . . . . . H2A H 0.520(4) 0.073(3) 0.2678(15) 0.071(11) Uiso 1 1 d . . . . . H2B H 0.432(4) 0.056(4) 0.2138(17) 0.085(12) Uiso 1 1 d . . . . . C2 C -0.2545(3) 0.3528(4) 0.21027(17) 0.0765(10) Uani 1 1 d . . . . . H2 H -0.3511 0.3573 0.2031 0.092 Uiso 1 1 calc R U . . . N3 N 0.1922(4) 0.0864(3) 0.14912(13) 0.0897(11) Uani 1 1 d . . . . . C3 C -0.2078(3) 0.2804(3) 0.25199(14) 0.0680(9) Uani 1 1 d . . . . . H3 H -0.2728 0.2368 0.2729 0.082 Uiso 1 1 calc R U . . . N4 N 0.3870(3) 0.5519(2) 0.44001(9) 0.0568(6) Uani 1 1 d . . . . . C4 C -0.0644(3) 0.2716(3) 0.26336(12) 0.0535(6) Uani 1 1 d . . . . . H4 H -0.0326 0.2215 0.2915 0.064 Uiso 1 1 calc R U . . . C5 C 0.0302(3) 0.3378(2) 0.23253(10) 0.0429(5) Uani 1 1 d . . . . . C6 C -0.0184(3) 0.4118(3) 0.19030(11) 0.0534(6) Uani 1 1 d . . . . . C7 C 0.2211(3) 0.4459(3) 0.19191(10) 0.0483(6) Uani 1 1 d . . . . . C8 C 0.1894(3) 0.3499(2) 0.23748(10) 0.0414(5) Uani 1 1 d . . . . . C9 C 0.2681(3) 0.2310(2) 0.22606(10) 0.0456(6) Uani 1 1 d . . . . . C10 C 0.3840(3) 0.1952(2) 0.25430(11) 0.0457(6) Uani 1 1 d . . . . . C11 C 0.3554(3) 0.3547(2) 0.31857(9) 0.0399(5) Uani 1 1 d . . . . . C12 C 0.2383(2) 0.4005(2) 0.29180(9) 0.0390(5) Uani 1 1 d . . . . . C13 C 0.1705(3) 0.4988(2) 0.31704(10) 0.0469(6) Uani 1 1 d . . . . . H13 H 0.0900 0.5318 0.3008 0.056 Uiso 1 1 calc R U . . . C14 C 0.2183(3) 0.5489(3) 0.36519(11) 0.0512(6) Uani 1 1 d . . . . . H14 H 0.1702 0.6155 0.3802 0.061 Uiso 1 1 calc R U . . . C15 C 0.3375(3) 0.5020(2) 0.39205(10) 0.0449(6) Uani 1 1 d . . . . . C16 C 0.4051(3) 0.4007(3) 0.36752(10) 0.0445(6) Uani 1 1 d . . . . . H16 H 0.4832 0.3647 0.3842 0.053 Uiso 1 1 calc R U . . . C17 C 0.2243(3) 0.1533(3) 0.18297(12) 0.0577(7) Uani 1 1 d . . . . . C18 C 0.3069(3) 0.6414(3) 0.47192(11) 0.0566(7) Uani 1 1 d . . . . . H18A H 0.2999 0.6124 0.5092 0.068 Uiso 1 1 calc R U . . . H18B H 0.2115 0.6468 0.4574 0.068 Uiso 1 1 calc R U . . . C19 C 0.3718(3) 0.7681(3) 0.47207(10) 0.0496(6) Uani 1 1 d . . . . . C20 C 0.4322(4) 0.8212(4) 0.42640(13) 0.0733(10) Uani 1 1 d . . . . . H20 H 0.4381 0.7772 0.3940 0.088 Uiso 1 1 calc R U . . . C21 C 0.4841(4) 0.9409(4) 0.42909(17) 0.0836(11) Uani 1 1 d . . . . . H21 H 0.5243 0.9768 0.3984 0.100 Uiso 1 1 calc R U . . . C22 C 0.4761(4) 1.0055(3) 0.47650(17) 0.0735(9) Uani 1 1 d . . . . . H22 H 0.5086 1.0862 0.4777 0.088 Uiso 1 1 calc R U . . . C23 C 0.4214(4) 0.9533(3) 0.52179(15) 0.0723(9) Uani 1 1 d . . . . . H23 H 0.4191 0.9971 0.5543 0.087 Uiso 1 1 calc R U . . . C24 C 0.3689(3) 0.8350(3) 0.51974(12) 0.0573(7) Uani 1 1 d . . . . . H24 H 0.3310 0.7998 0.5510 0.069 Uiso 1 1 calc R U . . . C25 C 0.5131(3) 0.5071(3) 0.46709(12) 0.0607(8) Uani 1 1 d . . . . . H25A H 0.5611 0.5763 0.4839 0.073 Uiso 1 1 calc R U . . . H25B H 0.5763 0.4732 0.4398 0.073 Uiso 1 1 calc R U . . . C26 C 0.4872(3) 0.4102(3) 0.51036(11) 0.0580(7) Uani 1 1 d . . . . . C27 C 0.5961(4) 0.3730(4) 0.54425(14) 0.0796(11) Uani 1 1 d . . . . . H27 H 0.6860 0.4069 0.5402 0.095 Uiso 1 1 calc R U . . . C28 C 0.5721(6) 0.2845(4) 0.58476(15) 0.0909(14) Uani 1 1 d . . . . . H28 H 0.6465 0.2593 0.6069 0.109 Uiso 1 1 calc R U . . . C29 C 0.4416(6) 0.2355(4) 0.59189(15) 0.0876(13) Uani 1 1 d . . . . . H29 H 0.4260 0.1780 0.6192 0.105 Uiso 1 1 calc R U . . . C30 C 0.3327(5) 0.2711(4) 0.55870(16) 0.0837(11) Uani 1 1 d . . . . . H30 H 0.2430 0.2372 0.5633 0.100 Uiso 1 1 calc R U . . . C31 C 0.3559(4) 0.3577(3) 0.51812(14) 0.0701(9) Uani 1 1 d . . . . . H31 H 0.2811 0.3807 0.4957 0.084 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 0.0674(14) 0.0860(15) 0.0486(10) 0.0029(10) 0.0067(10) -0.0260(12) N1 0.0691(16) 0.0613(16) 0.0506(13) 0.0171(12) -0.0099(12) -0.0045(13) C1 0.0622(19) 0.075(2) 0.082(2) 0.0002(18) -0.0269(17) 0.0118(16) O2 0.0422(9) 0.0580(11) 0.0561(10) -0.0184(9) -0.0106(8) 0.0097(8) N2 0.0546(14) 0.0611(16) 0.0686(16) -0.0232(13) -0.0123(13) 0.0144(12) C2 0.0416(16) 0.088(2) 0.100(3) -0.023(2) -0.0113(16) 0.0013(16) N3 0.113(3) 0.087(2) 0.0687(17) -0.0302(17) -0.0278(18) 0.002(2) C3 0.0484(15) 0.075(2) 0.080(2) -0.0174(18) 0.0067(15) -0.0151(15) N4 0.0658(15) 0.0564(14) 0.0483(12) -0.0157(10) -0.0097(11) 0.0017(12) C4 0.0543(15) 0.0529(16) 0.0534(14) -0.0038(12) 0.0003(12) -0.0097(12) C5 0.0426(13) 0.0431(13) 0.0430(12) -0.0059(10) -0.0041(10) -0.0006(10) C6 0.0540(15) 0.0514(16) 0.0549(15) -0.0007(12) -0.0111(12) 0.0011(12) C7 0.0560(15) 0.0524(14) 0.0364(12) -0.0033(10) 0.0001(11) -0.0091(12) C8 0.0426(13) 0.0444(13) 0.0371(11) -0.0009(10) -0.0006(10) -0.0019(10) C9 0.0457(13) 0.0505(14) 0.0407(12) -0.0068(10) -0.0028(10) -0.0011(11) C10 0.0407(12) 0.0474(14) 0.0489(13) -0.0099(11) 0.0015(10) -0.0024(10) C11 0.0394(12) 0.0391(12) 0.0413(11) -0.0026(10) 0.0010(10) -0.0028(10) C12 0.0411(12) 0.0400(12) 0.0360(10) 0.0016(9) 0.0012(9) -0.0025(10) C13 0.0523(14) 0.0455(13) 0.0429(12) 0.0026(11) -0.0039(11) 0.0065(11) C14 0.0621(16) 0.0443(14) 0.0471(13) -0.0070(11) -0.0008(12) 0.0092(12) C15 0.0520(14) 0.0432(13) 0.0395(12) -0.0025(10) -0.0007(10) -0.0078(11) C16 0.0418(13) 0.0472(14) 0.0444(13) -0.0014(10) -0.0057(10) -0.0022(11) C17 0.0590(16) 0.0620(17) 0.0523(15) -0.0106(14) -0.0096(13) 0.0043(14) C18 0.0674(18) 0.0607(17) 0.0416(13) -0.0092(12) 0.0007(12) -0.0060(14) C19 0.0519(14) 0.0544(15) 0.0425(13) -0.0035(11) -0.0015(11) 0.0028(12) C20 0.094(3) 0.078(2) 0.0477(16) -0.0019(14) 0.0116(16) -0.004(2) C21 0.085(3) 0.085(3) 0.080(2) 0.025(2) 0.0217(19) -0.006(2) C22 0.065(2) 0.0575(19) 0.098(3) -0.0023(18) 0.0032(19) -0.0026(16) C23 0.085(2) 0.0589(19) 0.073(2) -0.0166(16) 0.0034(18) -0.0029(17) C24 0.0662(17) 0.0549(17) 0.0506(14) -0.0091(12) 0.0042(13) 0.0000(14) C25 0.0582(17) 0.071(2) 0.0526(15) -0.0186(14) -0.0107(13) -0.0088(15) C26 0.0672(18) 0.0598(17) 0.0470(14) -0.0166(12) -0.0112(13) 0.0107(14) C27 0.068(2) 0.112(3) 0.0588(18) -0.0166(19) -0.0104(16) 0.026(2) C28 0.116(3) 0.099(3) 0.058(2) -0.0081(19) -0.021(2) 0.048(3) C29 0.143(4) 0.063(2) 0.0570(19) -0.0102(16) -0.009(2) 0.011(3) C30 0.111(3) 0.063(2) 0.077(2) -0.0030(18) -0.008(2) -0.014(2) C31 0.078(2) 0.0592(18) 0.0732(19) -0.0033(16) -0.0192(17) -0.0067(17) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C6 112.3(2) . . ? C7 N1 H1 123(3) . . ? C6 N1 H1 124(3) . . ? C2 C1 C6 118.0(3) . . ? C2 C1 H1A 121.0 . . ? C6 C1 H1A 121.0 . . ? C10 O2 C11 118.12(19) . . ? C10 N2 H2A 117(3) . . ? C10 N2 H2B 112(3) . . ? H2A N2 H2B 129(4) . . ? C3 C2 C1 121.5(3) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C15 N4 C25 122.5(2) . . ? C15 N4 C18 123.1(3) . . ? C25 N4 C18 113.8(2) . . ? C5 C4 C3 119.2(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 C8 130.3(2) . . ? C6 C5 C8 109.7(2) . . ? C1 C6 C5 120.9(3) . . ? C1 C6 N1 130.1(3) . . ? C5 C6 N1 108.9(2) . . ? O1 C7 N1 125.7(3) . . ? O1 C7 C8 126.4(3) . . ? N1 C7 C8 107.9(2) . . ? C5 C8 C12 113.9(2) . . ? C5 C8 C9 113.3(2) . . ? C12 C8 C9 108.9(2) . . ? C5 C8 C7 101.0(2) . . ? C12 C8 C7 109.3(2) . . ? C9 C8 C7 110.2(2) . . ? C10 C9 C17 116.6(3) . . ? C10 C9 C8 123.1(2) . . ? C17 C9 C8 120.3(2) . . ? N2 C10 C9 125.7(2) . . ? N2 C10 O2 110.7(2) . . ? C9 C10 O2 123.6(2) . . ? C12 C11 C16 123.7(2) . . ? C12 C11 O2 122.4(2) . . ? C16 C11 O2 113.9(2) . . ? C11 C12 C13 115.7(2) . . ? C11 C12 C8 122.2(2) . . ? C13 C12 C8 122.1(2) . . ? C14 C13 C12 122.5(2) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C13 C14 C15 121.4(3) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? N4 C15 C14 122.0(3) . . ? N4 C15 C16 121.4(3) . . ? C14 C15 C16 116.6(2) . . ? C11 C16 C15 120.1(2) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? N3 C17 C9 177.0(4) . . ? N4 C18 C19 113.6(3) . . ? N4 C18 H18A 108.8 . . ? C19 C18 H18A 108.8 . . ? N4 C18 H18B 108.8 . . ? C19 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C24 C19 C20 118.3(3) . . ? C24 C19 C18 118.5(3) . . ? C20 C19 C18 123.2(3) . . ? C19 C20 C21 119.8(3) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 120.3(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C23 C22 C21 120.5(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 120.0(3) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C19 C24 C23 121.1(3) . . ? C19 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? N4 C25 C26 115.1(3) . . ? N4 C25 H25A 108.5 . . ? C26 C25 H25A 108.5 . . ? N4 C25 H25B 108.5 . . ? C26 C25 H25B 108.5 . . ? H25A C25 H25B 107.5 . . ? C31 C26 C27 117.6(3) . . ? C31 C26 C25 122.0(3) . . ? C27 C26 C25 120.4(3) . . ? C26 C27 C28 120.5(4) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C29 C28 C27 120.6(4) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 119.7(4) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? C29 C30 C31 120.1(4) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? C26 C31 C30 121.5(3) . . ? C26 C31 H31 119.2 . . ? C30 C31 H31 119.2 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.210(3) . ? N1 C7 1.353(4) . ? N1 C6 1.403(4) . ? N1 H1 0.83(2) . ? C1 C2 1.382(5) . ? C1 C6 1.383(4) . ? C1 H1A 0.9300 . ? O2 C10 1.353(3) . ? O2 C11 1.399(3) . ? N2 C10 1.339(4) . ? N2 H2A 0.85(4) . ? N2 H2B 0.90(4) . ? C2 C3 1.365(5) . ? C2 H2 0.9300 . ? N3 C17 1.146(4) . ? C3 C4 1.385(4) . ? C3 H3 0.9300 . ? N4 C15 1.379(3) . ? N4 C25 1.447(4) . ? N4 C18 1.461(4) . ? C4 C5 1.374(4) . ? C4 H4 0.9300 . ? C5 C6 1.391(4) . ? C5 C8 1.513(3) . ? C7 C8 1.559(3) . ? C8 C12 1.515(3) . ? C8 C9 1.518(4) . ? C9 C10 1.352(4) . ? C9 C17 1.416(4) . ? C11 C12 1.379(3) . ? C11 C16 1.384(3) . ? C12 C13 1.392(3) . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 C15 1.401(4) . ? C14 H14 0.9300 . ? C15 C16 1.408(4) . ? C16 H16 0.9300 . ? C18 C19 1.508(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C24 1.379(4) . ? C19 C20 1.384(4) . ? C20 C21 1.393(6) . ? C20 H20 0.9300 . ? C21 C22 1.362(6) . ? C21 H21 0.9300 . ? C22 C23 1.351(5) . ? C22 H22 0.9300 . ? C23 C24 1.381(5) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.516(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C31 1.378(5) . ? C26 C27 1.383(5) . ? C27 C28 1.403(6) . ? C27 H27 0.9300 . ? C28 C29 1.353(7) . ? C28 H28 0.9300 . ? C29 C30 1.367(6) . ? C29 H29 0.9300 . ? C30 C31 1.389(5) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? 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 N2 H2A O1 0.85(4) 2.05(4) 2.885(4) 170(4) 4_645 N2 H2B N3 0.90(4) 2.78(4) 3.455(4) 132(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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(6) . . . . ? C1 C2 C3 C4 -0.4(5) . . . . ? C2 C3 C4 C5 0.8(5) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? C3 C4 C5 C8 176.9(3) . . . . ? C2 C1 C6 C5 0.7(5) . . . . ? C2 C1 C6 N1 -178.1(3) . . . . ? C4 C5 C6 C1 -0.3(4) . . . . ? C8 C5 C6 C1 -178.2(3) . . . . ? C4 C5 C6 N1 178.7(2) . . . . ? C8 C5 C6 N1 0.9(3) . . . . ? C7 N1 C6 C1 175.6(3) . . . . ? C7 N1 C6 C5 -3.4(3) . . . . ? C6 N1 C7 O1 -174.6(3) . . . . ? C6 N1 C7 C8 4.3(3) . . . . ? C4 C5 C8 C12 -59.1(4) . . . . ? C6 C5 C8 C12 118.4(2) . . . . ? C4 C5 C8 C9 66.1(3) . . . . ? C6 C5 C8 C9 -116.4(2) . . . . ? C4 C5 C8 C7 -176.1(3) . . . . ? C6 C5 C8 C7 1.4(3) . . . . ? O1 C7 C8 C5 175.5(3) . . . . ? N1 C7 C8 C5 -3.4(3) . . . . ? O1 C7 C8 C12 55.2(4) . . . . ? N1 C7 C8 C12 -123.7(2) . . . . ? O1 C7 C8 C9 -64.4(3) . . . . ? N1 C7 C8 C9 116.7(2) . . . . ? C5 C8 C9 C10 -141.6(3) . . . . ? C12 C8 C9 C10 -13.8(3) . . . . ? C7 C8 C9 C10 106.1(3) . . . . ? C5 C8 C9 C17 40.6(3) . . . . ? C12 C8 C9 C17 168.5(2) . . . . ? C7 C8 C9 C17 -71.7(3) . . . . ? C17 C9 C10 N2 4.6(4) . . . . ? C8 C9 C10 N2 -173.3(3) . . . . ? C17 C9 C10 O2 -176.0(3) . . . . ? C8 C9 C10 O2 6.2(4) . . . . ? C11 O2 C10 N2 -175.3(2) . . . . ? C11 O2 C10 C9 5.2(4) . . . . ? C10 O2 C11 C12 -7.0(3) . . . . ? C10 O2 C11 C16 172.3(2) . . . . ? C16 C11 C12 C13 0.3(4) . . . . ? O2 C11 C12 C13 179.6(2) . . . . ? C16 C11 C12 C8 178.3(2) . . . . ? O2 C11 C12 C8 -2.4(4) . . . . ? C5 C8 C12 C11 139.3(2) . . . . ? C9 C8 C12 C11 11.8(3) . . . . ? C7 C8 C12 C11 -108.6(3) . . . . ? C5 C8 C12 C13 -42.8(3) . . . . ? C9 C8 C12 C13 -170.3(2) . . . . ? C7 C8 C12 C13 69.3(3) . . . . ? C11 C12 C13 C14 1.1(4) . . . . ? C8 C12 C13 C14 -176.9(2) . . . . ? C12 C13 C14 C15 -1.0(4) . . . . ? C25 N4 C15 C14 -177.7(3) . . . . ? C18 N4 C15 C14 11.6(4) . . . . ? C25 N4 C15 C16 2.2(4) . . . . ? C18 N4 C15 C16 -168.5(3) . . . . ? C13 C14 C15 N4 179.5(3) . . . . ? C13 C14 C15 C16 -0.4(4) . . . . ? C12 C11 C16 C15 -1.7(4) . . . . ? O2 C11 C16 C15 178.9(2) . . . . ? N4 C15 C16 C11 -178.2(2) . . . . ? C14 C15 C16 C11 1.7(4) . . . . ? C15 N4 C18 C19 -111.5(3) . . . . ? C25 N4 C18 C19 77.0(3) . . . . ? N4 C18 C19 C24 -141.1(3) . . . . ? N4 C18 C19 C20 40.0(4) . . . . ? C24 C19 C20 C21 -2.0(5) . . . . ? C18 C19 C20 C21 177.0(3) . . . . ? C19 C20 C21 C22 0.3(6) . . . . ? C20 C21 C22 C23 1.8(6) . . . . ? C21 C22 C23 C24 -2.1(6) . . . . ? C20 C19 C24 C23 1.7(5) . . . . ? C18 C19 C24 C23 -177.3(3) . . . . ? C22 C23 C24 C19 0.3(6) . . . . ? C15 N4 C25 C26 -93.1(3) . . . . ? C18 N4 C25 C26 78.4(3) . . . . ? N4 C25 C26 C31 8.1(4) . . . . ? N4 C25 C26 C27 -170.8(3) . . . . ? C31 C26 C27 C28 0.2(5) . . . . ? C25 C26 C27 C28 179.2(3) . . . . ? C26 C27 C28 C29 -1.0(6) . . . . ? C27 C28 C29 C30 1.1(6) . . . . ? C28 C29 C30 C31 -0.4(6) . . . . ? C27 C26 C31 C30 0.5(5) . . . . ? C25 C26 C31 C30 -178.5(3) . . . . ? C29 C30 C31 C26 -0.4(6) . . . . ?