#------------------------------------------------------------------------------ #$Date: 2024-07-05 20:57:25 +0300 (Fri, 05 Jul 2024) $ #$Revision: 293258 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159920.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_7159920 loop_ _publ_author_name 'Gallardo-Rosas, D' 'Guevara-Vela, J M' 'Rocha-Rinza, T' 'Toscano, R. A.' 'López-Cortés, J G' 'Ortega-Alfaro, M C' _publ_section_title ; Structure and isomerization behavior relationships of new push-pull azo-pyrrole photoswitches. ; _journal_issue 20 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4123 _journal_page_last 4134 _journal_paper_doi 10.1039/d4ob00417e _journal_volume 22 _journal_year 2024 _chemical_absolute_configuration unk _chemical_formula_moiety 'C18 H16 N4' _chemical_formula_sum 'C18 H16 N4' _chemical_formula_weight 288.35 _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2019/2 _audit_update_record ; 2022-07-11 deposited with the CCDC. 2024-04-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.582(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.0543(16) _cell_length_b 7.6061(11) _cell_length_c 18.348(3) _cell_measurement_reflns_used 6064 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.60 _cell_measurement_theta_min 2.24 _cell_volume 1529.2(4) _computing_cell_refinement 'APEX3 v2019.1-0(Bruker, 2019)' _computing_data_collection 'APEX3 v2019.1-0(Bruker, 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker, 2014)' _computing_molecular_graphics 'SHELXLe (H\"ubschle et al, 2011)' _computing_publication_material 'CIFTAB V 2013/2 (Sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS-2012 (Bruker, 2013)' _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 8.333 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker Smart Apex CCD diffractometer 01-670-01' _diffrn_measurement_method \w-scans _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_unetI/netI 0.0740 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 27078 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.574 _diffrn_reflns_theta_min 2.293 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_correction_T_min 0.6411 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Sheldrick, 2012)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.252 _exptl_crystal_description plate _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.410 _exptl_crystal_size_mid 0.270 _exptl_crystal_size_min 0.096 _refine_diff_density_max 0.140 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; ? ; _refine_ls_extinction_coef 0.0070(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 400 _refine_ls_number_reflns 8575 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.998 _refine_ls_R_factor_all 0.1416 _refine_ls_R_factor_gt 0.0604 _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^)+(0.0569P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1182 _refine_ls_wR_factor_ref 0.1567 _reflns_Friedel_coverage 0.865 _reflns_Friedel_fraction_full 0.998 _reflns_Friedel_fraction_max 0.996 _reflns_number_gt 4185 _reflns_number_total 8575 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00417e2.cif _cod_data_source_block Compuesto_3b _cod_depositor_comments 'Adding full bibliography for 7159920.cif.' _cod_original_cell_volume 1529.3(4) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7159920 _shelx_shelxl_version_number 2019/2 _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 0.969 _shelx_estimated_absorpt_t_max 0.993 _shelx_res_file ; TITL Compuesto_3b Compuesto_3b.res created by SHELXL-2019/2 at 14:37:09 on 25-Jun-2022 CELL 0.71073 11.0543 7.6061 18.3485 90.000 97.582 90.000 ZERR 4.000 0.0016 0.0011 0.0027 0.000 0.003 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H N UNIT 72 64 16 OMIT 1 1 0 OMIT 0 0 1 OMIT -1 0 1 OMIT 0 0 2 OMIT 6 -8 1 OMIT 1 -1 0 OMIT 1 0 2 TEMP 25.000 SIZE 0.096 0.270 0.410 L.S. 20 ACTA CONF EQIV $1 x, y, z-1 HTAB C5 N17_$1 EQIV $2 x, y, z+1 HTAB C25 N37_$2 BOND $H LIST 4 FMAP 2 PLAN 5 WGHT 0.056900 EXTI 0.006954 FVAR 0.41900 N1 3 0.843272 0.787483 0.068352 11.00000 0.05999 0.05641 = 0.04279 -0.00045 0.01034 0.00185 N2 3 0.890572 0.759168 0.196811 11.00000 0.05800 0.05220 = 0.04154 -0.00190 0.00591 -0.00138 N3 3 0.967153 0.698045 0.248503 11.00000 0.05401 0.06451 = 0.04425 0.00460 0.00623 0.00031 C1 1 0.726767 0.872376 0.072384 11.00000 0.07376 0.08882 = 0.06013 -0.00476 0.00331 0.02965 AFIX 137 H1A 2 0.668836 0.786704 0.084490 11.00000 -1.50000 H1B 2 0.697762 0.924729 0.025734 11.00000 -1.50000 H1C 2 0.736637 0.961853 0.109595 11.00000 -1.50000 AFIX 0 C2 1 0.923051 0.729169 0.127536 11.00000 0.05260 0.04985 = 0.04345 0.00288 0.00717 -0.00050 C3 1 1.018828 0.646640 0.100919 11.00000 0.05581 0.07085 = 0.05689 0.00504 0.01095 0.00759 AFIX 43 H3 2 1.085901 0.595048 0.128771 11.00000 -1.20000 AFIX 0 C4 1 0.996872 0.654610 0.024975 11.00000 0.07279 0.07279 = 0.05435 -0.00238 0.02536 0.00447 AFIX 43 H4 2 1.046537 0.608955 -0.007561 11.00000 -1.20000 AFIX 0 C5 1 0.889280 0.741478 0.006438 11.00000 0.07750 0.06264 = 0.03824 -0.00034 0.01561 -0.00203 AFIX 43 H5 2 0.853308 0.765258 -0.041259 11.00000 -1.20000 AFIX 0 C6 1 0.878943 0.750174 0.464409 11.00000 0.04843 0.04727 = 0.03921 -0.00049 0.00208 -0.00188 C7 1 0.803446 0.826234 0.406119 11.00000 0.05588 0.06196 = 0.04638 -0.00023 0.00691 0.00981 AFIX 43 H7 2 0.734099 0.886720 0.415614 11.00000 -1.20000 AFIX 0 C8 1 0.828832 0.814208 0.334647 11.00000 0.05402 0.07056 = 0.04252 0.00630 0.00125 0.00697 AFIX 43 H8 2 0.776800 0.866061 0.296726 11.00000 -1.20000 AFIX 0 C9 1 0.932048 0.724706 0.319303 11.00000 0.05127 0.05352 = 0.03683 -0.00086 0.00516 -0.00216 C10 1 1.009787 0.653925 0.377282 11.00000 0.04962 0.06032 = 0.04776 0.00343 0.00735 0.00638 AFIX 43 H10 2 1.080984 0.598058 0.367946 11.00000 -1.20000 AFIX 0 C11 1 0.983750 0.664666 0.448245 11.00000 0.05352 0.05473 = 0.04260 0.00276 -0.00020 0.00446 AFIX 43 H11 2 1.036750 0.614209 0.486069 11.00000 -1.20000 AFIX 0 C12 1 0.845932 0.761009 0.538809 11.00000 0.05483 0.05269 = 0.04193 -0.00366 0.00527 -0.00044 AFIX 43 H12 2 0.774387 0.821460 0.543869 11.00000 -1.20000 AFIX 0 C13 1 0.905862 0.694947 0.599733 11.00000 0.05830 0.05342 = 0.04569 0.00108 0.00902 0.00294 AFIX 43 H13 2 0.976100 0.630905 0.595080 11.00000 -1.20000 AFIX 0 C14 1 0.872009 0.713133 0.674054 11.00000 0.05788 0.04817 = 0.03937 -0.00084 0.00520 -0.00595 C15 1 0.951389 0.660878 0.734573 11.00000 0.06125 0.07769 = 0.04453 0.00345 0.00395 0.01093 AFIX 43 H15 2 1.027058 0.613195 0.728915 11.00000 -1.20000 AFIX 0 C16 1 0.916581 0.680576 0.803720 11.00000 0.06832 0.09755 = 0.04593 0.00037 -0.00276 0.01051 AFIX 43 H16 2 0.971894 0.644884 0.843599 11.00000 -1.20000 AFIX 0 N17 3 0.811511 0.745735 0.818060 11.00000 0.07163 0.09160 = 0.04581 -0.00182 0.00864 0.00533 C18 1 0.736686 0.795085 0.759378 11.00000 0.06380 0.09018 = 0.05410 0.00628 0.01760 0.00817 AFIX 43 H18 2 0.661523 0.841575 0.766922 11.00000 -1.20000 AFIX 0 C19 1 0.761390 0.782977 0.688485 11.00000 0.05937 0.08360 = 0.04508 0.01132 0.00685 0.00435 AFIX 43 H19 2 0.704312 0.821385 0.649983 11.00000 -1.20000 AFIX 0 N21 3 0.428501 0.743306 0.901733 11.00000 0.05568 0.06089 = 0.04280 -0.00043 0.01073 -0.00046 N22 3 0.380619 0.744510 0.772865 11.00000 0.05920 0.05032 = 0.04334 0.00363 0.00539 -0.00105 N23 3 0.300875 0.790308 0.719662 11.00000 0.05666 0.05701 = 0.04713 -0.00034 0.00761 0.00475 C21 1 0.549219 0.674755 0.901373 11.00000 0.06460 0.10705 = 0.05478 0.00361 0.00569 0.01726 AFIX 137 H21A 2 0.603811 0.768953 0.893476 11.00000 -1.50000 H21B 2 0.548673 0.589792 0.862641 11.00000 -1.50000 H21C 2 0.576014 0.619613 0.947762 11.00000 -1.50000 AFIX 0 C22 1 0.345409 0.778434 0.840730 11.00000 0.05480 0.05163 = 0.04271 0.00178 0.00987 -0.00087 C23 1 0.242612 0.848512 0.864200 11.00000 0.06656 0.05921 = 0.06120 0.00010 0.01279 0.00677 AFIX 43 H23 2 0.172375 0.884756 0.834454 11.00000 -1.20000 AFIX 0 C24 1 0.262756 0.855213 0.939988 11.00000 0.07631 0.07255 = 0.06314 -0.00850 0.02838 0.00194 AFIX 43 H24 2 0.208096 0.896014 0.970534 11.00000 -1.20000 AFIX 0 C25 1 0.377539 0.791121 0.962288 11.00000 0.07810 0.06637 = 0.04762 -0.00502 0.01353 -0.00698 AFIX 43 H25 2 0.414400 0.781875 1.010712 11.00000 -1.20000 AFIX 0 C26 1 0.388187 0.720640 0.504534 11.00000 0.05045 0.04777 = 0.04528 -0.00116 0.00559 -0.00246 C27 1 0.464750 0.651196 0.564538 11.00000 0.05054 0.05597 = 0.05357 0.00104 0.00652 0.00831 AFIX 43 H27 2 0.534609 0.590729 0.555943 11.00000 -1.20000 AFIX 0 C28 1 0.440316 0.669235 0.635569 11.00000 0.05302 0.05310 = 0.04823 0.00286 0.00261 0.00549 AFIX 43 H28 2 0.492636 0.620790 0.674216 11.00000 -1.20000 AFIX 0 C29 1 0.336745 0.760492 0.649288 11.00000 0.05100 0.04863 = 0.04281 0.00172 0.00366 0.00100 C30 1 0.259992 0.829200 0.590816 11.00000 0.05079 0.06622 = 0.05480 0.00199 0.00602 0.01288 AFIX 43 H30 2 0.189866 0.888759 0.599579 11.00000 -1.20000 AFIX 0 C31 1 0.285191 0.811284 0.520248 11.00000 0.05860 0.06389 = 0.04686 0.00710 0.00031 0.00815 AFIX 43 H31 2 0.232548 0.860572 0.481958 11.00000 -1.20000 AFIX 0 C32 1 0.418970 0.697306 0.430424 11.00000 0.05767 0.05270 = 0.05358 0.00121 0.00910 0.00141 AFIX 43 H32 2 0.490918 0.636971 0.426279 11.00000 -1.20000 AFIX 0 C33 1 0.355528 0.752779 0.367868 11.00000 0.05405 0.06264 = 0.05098 -0.00105 0.00630 -0.00380 AFIX 43 H33 2 0.281806 0.808634 0.371733 11.00000 -1.20000 AFIX 0 C34 1 0.389212 0.735371 0.293928 11.00000 0.05494 0.05670 = 0.04705 0.00001 0.00506 -0.00518 C35 1 0.305955 0.775952 0.233527 11.00000 0.05778 0.09588 = 0.05263 0.00997 0.00693 0.00165 AFIX 43 H35 2 0.227858 0.813519 0.239618 11.00000 -1.20000 AFIX 0 C36 1 0.339206 0.760486 0.164426 11.00000 0.07219 0.12809 = 0.05084 0.02068 -0.00064 -0.01375 AFIX 43 H36 2 0.280651 0.787119 0.124782 11.00000 -1.20000 AFIX 0 N37 3 0.448174 0.710594 0.149706 11.00000 0.08463 0.09675 = 0.05092 0.00713 0.01551 -0.00357 C38 1 0.528637 0.673676 0.208437 11.00000 0.07526 0.07330 = 0.06038 0.00552 0.01898 0.00346 AFIX 43 H38 2 0.606437 0.638453 0.200582 11.00000 -1.20000 AFIX 0 C39 1 0.504229 0.684225 0.279477 11.00000 0.06138 0.06431 = 0.05463 0.00391 0.00527 0.00292 AFIX 43 H39 2 0.564641 0.657154 0.318065 11.00000 -1.20000 AFIX 0 HKLF 4 REM Compuesto_3b REM wR2 = 0.1567, GooF = S = 0.998, Restrained GooF = 0.998 for all data REM R1 = 0.0604 for 4185 Fo > 4sig(Fo) and 0.1416 for all 8575 data REM 400 parameters refined using 1 restraints END WGHT 0.0569 0.0000 REM Highest difference peak 0.140, deepest hole -0.188, 1-sigma level 0.035 Q1 1 0.4732 0.7373 1.0170 11.00000 0.05 0.14 Q2 1 0.2307 0.9137 0.4682 11.00000 0.05 0.14 Q3 1 0.1878 0.9870 0.5950 11.00000 0.05 0.14 Q4 1 0.5207 0.6417 0.2904 11.00000 0.05 0.13 Q5 1 0.7844 0.8888 0.2403 11.00000 0.05 0.13 ; _shelx_res_checksum 59128 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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.8433(3) 0.7875(4) 0.06835(15) 0.0527(8) Uani 1 1 d . . . . . N2 N 0.8906(3) 0.7592(4) 0.19681(15) 0.0506(7) Uani 1 1 d . . . . . N3 N 0.9672(3) 0.6980(4) 0.24850(15) 0.0543(8) Uani 1 1 d . . . . . C1 C 0.7268(4) 0.8724(6) 0.0724(2) 0.0747(13) Uani 1 1 d . . . . . H1A H 0.668836 0.786704 0.084490 0.112 Uiso 1 1 calc R U . . . H1B H 0.697762 0.924729 0.025734 0.112 Uiso 1 1 calc R U . . . H1C H 0.736637 0.961853 0.109595 0.112 Uiso 1 1 calc R U . . . C2 C 0.9231(3) 0.7292(5) 0.12754(17) 0.0486(9) Uani 1 1 d . . . . . C3 C 1.0188(3) 0.6466(6) 0.10092(19) 0.0609(10) Uani 1 1 d . . . . . H3 H 1.085901 0.595048 0.128771 0.073 Uiso 1 1 calc R U . . . C4 C 0.9969(4) 0.6546(6) 0.02498(19) 0.0651(11) Uani 1 1 d . . . . . H4 H 1.046537 0.608955 -0.007561 0.078 Uiso 1 1 calc R U . . . C5 C 0.8893(3) 0.7415(6) 0.00644(18) 0.0587(10) Uani 1 1 d . . . . . H5 H 0.853308 0.765258 -0.041259 0.070 Uiso 1 1 calc R U . . . C6 C 0.8789(3) 0.7502(5) 0.46441(17) 0.0453(8) Uani 1 1 d . . . . . C7 C 0.8034(3) 0.8262(5) 0.40612(18) 0.0547(10) Uani 1 1 d . . . . . H7 H 0.734099 0.886720 0.415614 0.066 Uiso 1 1 calc R U . . . C8 C 0.8288(3) 0.8142(6) 0.33465(18) 0.0562(10) Uani 1 1 d . . . . . H8 H 0.776800 0.866061 0.296726 0.067 Uiso 1 1 calc R U . . . C9 C 0.9320(3) 0.7247(5) 0.31930(17) 0.0473(9) Uani 1 1 d . . . . . C10 C 1.0098(3) 0.6539(5) 0.37728(18) 0.0525(9) Uani 1 1 d . . . . . H10 H 1.080984 0.598058 0.367946 0.063 Uiso 1 1 calc R U . . . C11 C 0.9838(3) 0.6647(5) 0.44824(17) 0.0509(9) Uani 1 1 d . . . . . H11 H 1.036750 0.614209 0.486069 0.061 Uiso 1 1 calc R U . . . C12 C 0.8459(3) 0.7610(5) 0.53881(17) 0.0499(9) Uani 1 1 d . . . . . H12 H 0.774387 0.821460 0.543869 0.060 Uiso 1 1 calc R U . . . C13 C 0.9059(3) 0.6949(5) 0.59973(18) 0.0523(10) Uani 1 1 d . . . . . H13 H 0.976100 0.630905 0.595080 0.063 Uiso 1 1 calc R U . . . C14 C 0.8720(3) 0.7131(5) 0.67405(17) 0.0486(9) Uani 1 1 d . . . . . C15 C 0.9514(3) 0.6609(6) 0.73457(18) 0.0614(11) Uani 1 1 d . . . . . H15 H 1.027058 0.613195 0.728915 0.074 Uiso 1 1 calc R U . . . C16 C 0.9166(4) 0.6806(6) 0.8037(2) 0.0715(12) Uani 1 1 d . . . . . H16 H 0.971894 0.644884 0.843599 0.086 Uiso 1 1 calc R U . . . N17 N 0.8115(3) 0.7457(5) 0.81806(16) 0.0696(10) Uani 1 1 d . . . . . C18 C 0.7367(4) 0.7951(6) 0.7594(2) 0.0685(13) Uani 1 1 d . . . . . H18 H 0.661523 0.841575 0.766922 0.082 Uiso 1 1 calc R U . . . C19 C 0.7614(3) 0.7830(6) 0.68849(19) 0.0627(12) Uani 1 1 d . . . . . H19 H 0.704312 0.821385 0.649983 0.075 Uiso 1 1 calc R U . . . N21 N 0.4285(3) 0.7433(4) 0.90173(15) 0.0527(7) Uani 1 1 d . . . . . N22 N 0.3806(3) 0.7445(4) 0.77286(15) 0.0511(8) Uani 1 1 d . . . . . N23 N 0.3009(3) 0.7903(4) 0.71966(15) 0.0535(8) Uani 1 1 d . . . . . C21 C 0.5492(3) 0.6748(6) 0.9014(2) 0.0757(13) Uani 1 1 d . . . . . H21A H 0.603811 0.768953 0.893476 0.114 Uiso 1 1 calc R U . . . H21B H 0.548673 0.589792 0.862641 0.114 Uiso 1 1 calc R U . . . H21C H 0.576014 0.619613 0.947762 0.114 Uiso 1 1 calc R U . . . C22 C 0.3454(3) 0.7784(5) 0.84073(18) 0.0494(9) Uani 1 1 d . . . . . C23 C 0.2426(4) 0.8485(5) 0.8642(2) 0.0619(10) Uani 1 1 d . . . . . H23 H 0.172375 0.884756 0.834454 0.074 Uiso 1 1 calc R U . . . C24 C 0.2628(4) 0.8552(6) 0.9400(2) 0.0690(11) Uani 1 1 d . . . . . H24 H 0.208096 0.896014 0.970534 0.083 Uiso 1 1 calc R U . . . C25 C 0.3775(4) 0.7911(6) 0.9623(2) 0.0636(11) Uani 1 1 d . . . . . H25 H 0.414400 0.781875 1.010712 0.076 Uiso 1 1 calc R U . . . C26 C 0.3882(3) 0.7206(5) 0.50453(17) 0.0479(9) Uani 1 1 d . . . . . C27 C 0.4648(3) 0.6512(5) 0.56454(19) 0.0534(9) Uani 1 1 d . . . . . H27 H 0.534609 0.590729 0.555943 0.064 Uiso 1 1 calc R U . . . C28 C 0.4403(3) 0.6692(5) 0.63557(18) 0.0518(9) Uani 1 1 d . . . . . H28 H 0.492636 0.620790 0.674216 0.062 Uiso 1 1 calc R U . . . C29 C 0.3367(3) 0.7605(5) 0.64929(18) 0.0477(9) Uani 1 1 d . . . . . C30 C 0.2600(3) 0.8292(6) 0.59082(19) 0.0574(10) Uani 1 1 d . . . . . H30 H 0.189866 0.888759 0.599579 0.069 Uiso 1 1 calc R U . . . C31 C 0.2852(3) 0.8113(5) 0.52025(19) 0.0570(10) Uani 1 1 d . . . . . H31 H 0.232548 0.860572 0.481958 0.068 Uiso 1 1 calc R U . . . C32 C 0.4190(3) 0.6973(5) 0.43042(19) 0.0545(10) Uani 1 1 d . . . . . H32 H 0.490918 0.636971 0.426279 0.065 Uiso 1 1 calc R U . . . C33 C 0.3555(3) 0.7528(6) 0.36787(19) 0.0559(10) Uani 1 1 d . . . . . H33 H 0.281806 0.808634 0.371733 0.067 Uiso 1 1 calc R U . . . C34 C 0.3892(3) 0.7354(5) 0.29393(18) 0.0530(9) Uani 1 1 d . . . . . C35 C 0.3060(4) 0.7760(6) 0.2335(2) 0.0688(13) Uani 1 1 d . . . . . H35 H 0.227858 0.813519 0.239618 0.083 Uiso 1 1 calc R U . . . C36 C 0.3392(4) 0.7605(8) 0.1644(2) 0.0845(15) Uani 1 1 d . . . . . H36 H 0.280651 0.787119 0.124782 0.101 Uiso 1 1 calc R U . . . N37 N 0.4482(3) 0.7106(6) 0.14971(17) 0.0768(11) Uani 1 1 d . . . . . C38 C 0.5286(4) 0.6737(6) 0.2084(2) 0.0687(12) Uani 1 1 d . . . . . H38 H 0.606437 0.638453 0.200582 0.082 Uiso 1 1 calc R U . . . C39 C 0.5042(3) 0.6842(5) 0.2795(2) 0.0603(10) Uani 1 1 d . . . . . H39 H 0.564641 0.657154 0.318065 0.072 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 N1 0.0600(18) 0.056(2) 0.0428(16) -0.0004(14) 0.0103(13) 0.0019(16) N2 0.0580(18) 0.0522(19) 0.0415(16) -0.0019(15) 0.0059(13) -0.0014(17) N3 0.0540(17) 0.065(2) 0.0442(16) 0.0046(16) 0.0062(14) 0.0003(17) C1 0.074(3) 0.089(3) 0.060(3) -0.005(2) 0.003(2) 0.030(3) C2 0.053(2) 0.050(2) 0.0434(19) 0.0029(17) 0.0072(16) -0.0005(18) C3 0.056(2) 0.071(3) 0.057(2) 0.005(2) 0.0110(18) 0.008(2) C4 0.073(3) 0.073(3) 0.054(2) -0.002(2) 0.0254(19) 0.004(2) C5 0.078(3) 0.063(3) 0.0382(19) -0.0003(18) 0.0156(18) -0.002(2) C6 0.0484(19) 0.047(2) 0.0392(18) -0.0005(17) 0.0021(15) -0.0019(18) C7 0.056(2) 0.062(3) 0.046(2) -0.0002(19) 0.0069(17) 0.010(2) C8 0.054(2) 0.071(3) 0.043(2) 0.0063(19) 0.0013(16) 0.007(2) C9 0.051(2) 0.054(2) 0.0368(18) -0.0009(17) 0.0052(15) -0.0022(19) C10 0.050(2) 0.060(2) 0.048(2) 0.0034(18) 0.0073(16) 0.0064(19) C11 0.054(2) 0.055(2) 0.0426(18) 0.0028(18) -0.0002(15) 0.0045(19) C12 0.055(2) 0.053(2) 0.0419(18) -0.0037(18) 0.0053(15) -0.0004(19) C13 0.058(2) 0.053(2) 0.0457(19) 0.0011(18) 0.0090(17) 0.0029(19) C14 0.058(2) 0.048(2) 0.0394(18) -0.0008(16) 0.0052(16) -0.0059(18) C15 0.061(2) 0.078(3) 0.045(2) 0.003(2) 0.0039(17) 0.011(2) C16 0.068(3) 0.098(4) 0.046(2) 0.000(2) -0.0028(18) 0.011(3) N17 0.072(2) 0.092(3) 0.0458(18) -0.0018(19) 0.0086(16) 0.005(2) C18 0.064(3) 0.090(4) 0.054(2) 0.006(2) 0.018(2) 0.008(2) C19 0.059(2) 0.084(3) 0.045(2) 0.011(2) 0.0068(17) 0.004(2) N21 0.0557(17) 0.061(2) 0.0428(16) -0.0004(15) 0.0107(13) -0.0005(17) N22 0.0592(18) 0.0503(19) 0.0433(16) 0.0036(15) 0.0054(14) -0.0010(16) N23 0.0567(18) 0.057(2) 0.0471(17) -0.0003(15) 0.0076(14) 0.0048(17) C21 0.065(2) 0.107(4) 0.055(2) 0.004(2) 0.0057(19) 0.017(3) C22 0.055(2) 0.052(2) 0.0427(19) 0.0018(17) 0.0099(16) -0.0009(19) C23 0.067(3) 0.059(2) 0.061(2) 0.000(2) 0.013(2) 0.007(2) C24 0.076(3) 0.073(3) 0.063(3) -0.009(2) 0.028(2) 0.002(2) C25 0.078(3) 0.066(3) 0.048(2) -0.0050(19) 0.0135(19) -0.007(2) C26 0.050(2) 0.048(2) 0.045(2) -0.0012(17) 0.0056(15) -0.0025(18) C27 0.051(2) 0.056(2) 0.054(2) 0.0010(19) 0.0065(17) 0.008(2) C28 0.053(2) 0.053(2) 0.048(2) 0.0029(18) 0.0026(16) 0.0055(19) C29 0.051(2) 0.049(2) 0.0428(19) 0.0017(18) 0.0037(15) 0.001(2) C30 0.051(2) 0.066(3) 0.055(2) 0.002(2) 0.0060(17) 0.013(2) C31 0.059(2) 0.064(3) 0.047(2) 0.007(2) 0.0003(17) 0.008(2) C32 0.058(2) 0.053(2) 0.054(2) 0.0012(19) 0.0091(17) 0.001(2) C33 0.054(2) 0.063(3) 0.051(2) -0.001(2) 0.0063(17) -0.004(2) C34 0.055(2) 0.057(2) 0.047(2) 0.000(2) 0.0051(17) -0.005(2) C35 0.058(2) 0.096(4) 0.053(2) 0.010(2) 0.0069(18) 0.002(3) C36 0.072(3) 0.128(5) 0.051(2) 0.021(3) -0.001(2) -0.014(3) N37 0.085(3) 0.097(3) 0.051(2) 0.007(2) 0.0155(18) -0.004(2) C38 0.075(3) 0.073(3) 0.060(2) 0.006(2) 0.019(2) 0.003(2) C39 0.061(2) 0.064(3) 0.055(2) 0.004(2) 0.0053(18) 0.003(2) 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' 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 C5 N1 C2 107.8(3) . . ? C5 N1 C1 126.4(3) . . ? C2 N1 C1 125.6(3) . . ? N3 N2 C2 113.3(3) . . ? N2 N3 C9 113.2(3) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 N1 108.0(3) . . ? C3 C2 N2 135.0(3) . . ? N1 C2 N2 117.0(3) . . ? C2 C3 C4 107.3(3) . . ? C2 C3 H3 126.4 . . ? C4 C3 H3 126.4 . . ? C5 C4 C3 107.7(3) . . ? C5 C4 H4 126.2 . . ? C3 C4 H4 126.2 . . ? N1 C5 C4 109.2(3) . . ? N1 C5 H5 125.4 . . ? C4 C5 H5 125.4 . . ? C7 C6 C11 117.5(3) . . ? C7 C6 C12 119.7(3) . . ? C11 C6 C12 122.8(3) . . ? C8 C7 C6 121.7(3) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 120.0(3) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 118.5(3) . . ? C10 C9 N3 115.5(3) . . ? C8 C9 N3 125.9(3) . . ? C11 C10 C9 121.3(3) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C6 120.9(3) . . ? C10 C11 H11 119.5 . . ? C6 C11 H11 119.5 . . ? C13 C12 C6 127.6(3) . . ? C13 C12 H12 116.2 . . ? C6 C12 H12 116.2 . . ? C12 C13 C14 126.1(4) . . ? C12 C13 H13 116.9 . . ? C14 C13 H13 116.9 . . ? C15 C14 C19 116.0(3) . . ? C15 C14 C13 120.5(3) . . ? C19 C14 C13 123.5(3) . . ? C14 C15 C16 118.9(4) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? N17 C16 C15 125.6(4) . . ? N17 C16 H16 117.2 . . ? C15 C16 H16 117.2 . . ? C16 N17 C18 114.6(3) . . ? N17 C18 C19 125.0(4) . . ? N17 C18 H18 117.5 . . ? C19 C18 H18 117.5 . . ? C18 C19 C14 119.9(3) . . ? C18 C19 H19 120.1 . . ? C14 C19 H19 120.1 . . ? C25 N21 C22 108.0(3) . . ? C25 N21 C21 126.0(3) . . ? C22 N21 C21 126.0(3) . . ? N23 N22 C22 113.1(3) . . ? N22 N23 C29 113.9(3) . . ? N21 C21 H21A 109.5 . . ? N21 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N21 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 N22 134.4(3) . . ? C23 C22 N21 108.1(3) . . ? N22 C22 N21 117.4(3) . . ? C22 C23 C24 107.4(4) . . ? C22 C23 H23 126.3 . . ? C24 C23 H23 126.3 . . ? C25 C24 C23 107.9(4) . . ? C25 C24 H24 126.0 . . ? C23 C24 H24 126.0 . . ? N21 C25 C24 108.6(3) . . ? N21 C25 H25 125.7 . . ? C24 C25 H25 125.7 . . ? C31 C26 C27 116.7(3) . . ? C31 C26 C32 123.5(3) . . ? C27 C26 C32 119.8(3) . . ? C28 C27 C26 122.3(3) . . ? C28 C27 H27 118.8 . . ? C26 C27 H27 118.8 . . ? C27 C28 C29 119.5(3) . . ? C27 C28 H28 120.3 . . ? C29 C28 H28 120.3 . . ? C30 C29 C28 119.0(3) . . ? C30 C29 N23 115.5(3) . . ? C28 C29 N23 125.5(3) . . ? C31 C30 C29 121.2(4) . . ? C31 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? C30 C31 C26 121.3(3) . . ? C30 C31 H31 119.3 . . ? C26 C31 H31 119.3 . . ? C33 C32 C26 127.2(4) . . ? C33 C32 H32 116.4 . . ? C26 C32 H32 116.4 . . ? C32 C33 C34 127.0(4) . . ? C32 C33 H33 116.5 . . ? C34 C33 H33 116.5 . . ? C35 C34 C39 116.1(3) . . ? C35 C34 C33 120.1(3) . . ? C39 C34 C33 123.7(3) . . ? C36 C35 C34 119.5(4) . . ? C36 C35 H35 120.3 . . ? C34 C35 H35 120.3 . . ? N37 C36 C35 125.1(4) . . ? N37 C36 H36 117.4 . . ? C35 C36 H36 117.4 . . ? C36 N37 C38 115.0(3) . . ? N37 C38 C39 124.3(4) . . ? N37 C38 H38 117.9 . . ? C39 C38 H38 117.9 . . ? C38 C39 C34 119.9(4) . . ? C38 C39 H39 120.0 . . ? C34 C39 H39 120.0 . . ? 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 N1 C5 1.351(4) . ? N1 C2 1.379(4) . ? N1 C1 1.451(5) . ? N2 N3 1.273(3) . ? N2 C2 1.385(4) . ? N3 C9 1.419(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.375(5) . ? C3 C4 1.384(5) . ? C3 H3 0.9300 . ? C4 C5 1.364(5) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.393(4) . ? C6 C11 1.394(4) . ? C6 C12 1.461(4) . ? C7 C8 1.380(4) . ? C7 H7 0.9300 . ? C8 C9 1.389(5) . ? C8 H8 0.9300 . ? C9 C10 1.385(4) . ? C10 C11 1.373(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.321(4) . ? C12 H12 0.9300 . ? C13 C14 1.467(4) . ? C13 H13 0.9300 . ? C14 C15 1.380(4) . ? C14 C19 1.390(5) . ? C15 C16 1.382(5) . ? C15 H15 0.9300 . ? C16 N17 1.321(5) . ? C16 H16 0.9300 . ? N17 C18 1.323(4) . ? C18 C19 1.367(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? N21 C25 1.360(4) . ? N21 C22 1.377(4) . ? N21 C21 1.434(4) . ? N22 N23 1.274(3) . ? N22 C22 1.377(4) . ? N23 C29 1.418(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.375(5) . ? C23 C24 1.380(5) . ? C23 H23 0.9300 . ? C24 C25 1.370(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C31 1.393(5) . ? C26 C27 1.401(4) . ? C26 C32 1.455(4) . ? C27 C28 1.372(4) . ? C27 H27 0.9300 . ? C28 C29 1.390(5) . ? C28 H28 0.9300 . ? C29 C30 1.380(4) . ? C30 C31 1.367(5) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 C33 1.332(4) . ? C32 H32 0.9300 . ? C33 C34 1.459(5) . ? C33 H33 0.9300 . ? C34 C35 1.379(5) . ? C34 C39 1.388(5) . ? C35 C36 1.371(5) . ? C35 H35 0.9300 . ? C36 N37 1.324(5) . ? C36 H36 0.9300 . ? N37 C38 1.334(5) . ? C38 C39 1.368(5) . ? C38 H38 0.9300 . ? C39 H39 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 _geom_hbond_publ_flag C5 H5 N17 0.93 2.57 3.450(5) 159.0 1_554 yes C25 H25 N37 0.93 2.59 3.479(5) 161.1 1_556 yes 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 C2 N2 N3 C9 -178.4(3) . . . . ? C5 N1 C2 C3 0.0(4) . . . . ? C1 N1 C2 C3 176.2(4) . . . . ? C5 N1 C2 N2 -178.2(3) . . . . ? C1 N1 C2 N2 -2.1(6) . . . . ? N3 N2 C2 C3 0.8(6) . . . . ? N3 N2 C2 N1 178.4(3) . . . . ? N1 C2 C3 C4 -0.1(5) . . . . ? N2 C2 C3 C4 177.7(4) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C2 N1 C5 C4 0.1(4) . . . . ? C1 N1 C5 C4 -176.0(4) . . . . ? C3 C4 C5 N1 -0.2(5) . . . . ? C11 C6 C7 C8 1.7(6) . . . . ? C12 C6 C7 C8 -177.8(3) . . . . ? C6 C7 C8 C9 -0.1(6) . . . . ? C7 C8 C9 C10 -2.1(6) . . . . ? C7 C8 C9 N3 178.1(4) . . . . ? N2 N3 C9 C10 177.4(3) . . . . ? N2 N3 C9 C8 -2.8(6) . . . . ? C8 C9 C10 C11 2.7(6) . . . . ? N3 C9 C10 C11 -177.5(3) . . . . ? C9 C10 C11 C6 -1.1(6) . . . . ? C7 C6 C11 C10 -1.1(5) . . . . ? C12 C6 C11 C10 178.4(3) . . . . ? C7 C6 C12 C13 179.1(4) . . . . ? C11 C6 C12 C13 -0.3(6) . . . . ? C6 C12 C13 C14 177.9(3) . . . . ? C12 C13 C14 C15 -170.2(4) . . . . ? C12 C13 C14 C19 9.4(6) . . . . ? C19 C14 C15 C16 0.1(6) . . . . ? C13 C14 C15 C16 179.8(4) . . . . ? C14 C15 C16 N17 0.3(7) . . . . ? C15 C16 N17 C18 -0.3(7) . . . . ? C16 N17 C18 C19 -0.1(7) . . . . ? N17 C18 C19 C14 0.5(7) . . . . ? C15 C14 C19 C18 -0.5(6) . . . . ? C13 C14 C19 C18 179.9(4) . . . . ? C22 N22 N23 C29 178.5(3) . . . . ? N23 N22 C22 C23 1.1(6) . . . . ? N23 N22 C22 N21 -176.2(3) . . . . ? C25 N21 C22 C23 0.0(4) . . . . ? C21 N21 C22 C23 -177.8(4) . . . . ? C25 N21 C22 N22 178.0(3) . . . . ? C21 N21 C22 N22 0.2(6) . . . . ? N22 C22 C23 C24 -177.8(4) . . . . ? N21 C22 C23 C24 -0.4(5) . . . . ? C22 C23 C24 C25 0.6(5) . . . . ? C22 N21 C25 C24 0.3(4) . . . . ? C21 N21 C25 C24 178.1(4) . . . . ? C23 C24 C25 N21 -0.5(5) . . . . ? C31 C26 C27 C28 0.5(6) . . . . ? C32 C26 C27 C28 180.0(3) . . . . ? C26 C27 C28 C29 -0.5(6) . . . . ? C27 C28 C29 C30 0.8(5) . . . . ? C27 C28 C29 N23 -179.5(3) . . . . ? N22 N23 C29 C30 -171.9(3) . . . . ? N22 N23 C29 C28 8.4(5) . . . . ? C28 C29 C30 C31 -1.0(6) . . . . ? N23 C29 C30 C31 179.2(3) . . . . ? C29 C30 C31 C26 1.0(6) . . . . ? C27 C26 C31 C30 -0.7(6) . . . . ? C32 C26 C31 C30 179.8(4) . . . . ? C31 C26 C32 C33 -1.5(6) . . . . ? C27 C26 C32 C33 179.1(4) . . . . ? C26 C32 C33 C34 177.3(4) . . . . ? C32 C33 C34 C35 170.4(4) . . . . ? C32 C33 C34 C39 -11.7(6) . . . . ? C39 C34 C35 C36 1.4(7) . . . . ? C33 C34 C35 C36 179.4(4) . . . . ? C34 C35 C36 N37 -0.9(8) . . . . ? C35 C36 N37 C38 0.1(8) . . . . ? C36 N37 C38 C39 0.2(7) . . . . ? N37 C38 C39 C34 0.3(7) . . . . ? C35 C34 C39 C38 -1.1(6) . . . . ? C33 C34 C39 C38 -179.1(4) . . . . ?