#------------------------------------------------------------------------------ #$Date: 2020-05-23 07:18:32 +0300 (Sat, 23 May 2020) $ #$Revision: 252308 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240580.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_7240580 loop_ _publ_author_name 'Patel, Divyang M.' 'Patel, Hetal J.' 'Padr\'on, Jos\'e M.' 'Patel, Hitendra M.' _publ_section_title ; A novel substrate directed multicomponent reaction for the syntheses of tetrahydro-spiro[pyrazolo[4,3-f]quinoline]-8,5′-pyrimidines and tetrahydro-pyrazolo[4,3-f]pyrimido[4,5-b]quinolines via selective multiple C--C bond formation under metal-free conditions ; _journal_issue 33 _journal_name_full 'RSC Advances' _journal_page_first 19600 _journal_paper_doi 10.1039/D0RA02990D _journal_volume 10 _journal_year 2020 _chemical_absolute_configuration unk _chemical_formula_moiety 'C29 H27 N5 O5' _chemical_formula_sum 'C29 H27 N5 O5' _chemical_formula_weight 525.55 _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 geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-01-29 deposited with the CCDC. 2020-05-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.2814(14) _cell_length_b 12.4871(16) _cell_length_c 16.249(2) _cell_measurement_reflns_used 4174 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.3 _cell_measurement_theta_min 2.3 _cell_volume 2491.9(5) _computing_cell_refinement 'SAINT V8.38A (BRUKER AXS INC.,2017)' _computing_data_collection 'APEX3 INC. BRUKER SOFTWARE PACKAGE' _computing_data_reduction 'SAINT V8.38A (BRUKER AXS INC.,2017)' _computing_molecular_graphics 'ORTEP,MERCURY AND PLATON' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXLT-2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'BRUKER D8 VENTURE PHOTON-200' _diffrn_measurement_method 'PHI AND OMEGA SCAN' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_unetI/netI 0.0411 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 24215 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.342 _diffrn_reflns_theta_min 2.326 _diffrn_source 'FINE FOCUS SEALED TUBE' _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS-2016/2 _exptl_crystal_colour WHITE _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_meas 1.4 _exptl_crystal_density_method 'NOT MEASURED' _exptl_crystal_description 'BLOCK TYPE' _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.396 _exptl_crystal_size_mid 0.356 _exptl_crystal_size_min 0.316 _exptl_transmission_factor_max 0.7454 _exptl_transmission_factor_min 0.5287 _refine_diff_density_max 0.561 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.046 _refine_ls_abs_structure_details ; Flack x determined using 1587 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.6(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 352 _refine_ls_number_reflns 5062 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0517 _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^)+(0.0801P)^2^+0.6253P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1406 _refine_ls_wR_factor_ref 0.1520 _reflns_Friedel_coverage 0.772 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.995 _reflns_number_gt 4174 _reflns_number_total 5062 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02990d2.cif _cod_data_source_block shelx _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_absolute_configuration' value 'UNK' was changed to 'unk' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. data item '_exptl_absorpt_correction_type' value 'MULTI SCAN' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_cell_volume 2492.0(5) _cod_database_code 7240580 _shelx_shelxl_version_number 2018/3 _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_res_file ; TITL SIR97 run in space group P 21 21 21 shelx.res created by SHELXL-2018/3 at 16:18:37 on 29-Jan-2020 CELL 0.71073 12.2814 12.4871 16.2494 90.000 90.000 90.000 ZERR 4.00 0.0014 0.0016 0.0021 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 116 108 20 20 MERG 2 FMAP 2 PLAN 25 ACTA BOND $H CONF L.S. 10 TEMP 20.00 WGHT 0.080100 0.625300 FVAR 0.18985 N5 3 0.341370 0.075819 0.920992 11.00000 0.04346 0.04192 = 0.05390 -0.01101 -0.00473 0.00390 O4 4 0.300918 -0.101148 0.917504 11.00000 0.08069 0.03532 = 0.08443 -0.00009 -0.00607 0.01078 O5 4 0.019173 0.129878 0.929892 11.00000 0.04151 0.05468 = 0.06547 0.00635 0.00057 -0.00267 O3 4 0.382085 0.251311 0.913846 11.00000 0.04777 0.04572 = 0.07002 0.00203 -0.00200 -0.00719 N4 3 0.160333 0.014474 0.922781 11.00000 0.05068 0.03364 = 0.04809 0.00076 -0.00179 -0.00696 C6 1 0.178297 0.258972 1.021644 11.00000 0.05260 0.03557 = 0.03130 0.00098 -0.00259 0.00450 AFIX 13 H6 2 0.100418 0.273367 1.028734 11.00000 -1.20000 AFIX 0 C7 1 0.196051 0.409298 0.889462 11.00000 0.04908 0.03031 = 0.04307 0.00200 -0.00037 0.00497 C8 1 0.311962 0.183174 0.920075 11.00000 0.04537 0.03780 = 0.03465 -0.00195 -0.00450 -0.00194 C9 1 0.152754 0.297806 0.870204 11.00000 0.04294 0.03557 = 0.03510 0.00442 -0.00065 0.00329 AFIX 13 H9 2 0.074209 0.302434 0.880227 11.00000 -1.20000 AFIX 0 N3 3 0.233933 0.359128 1.029884 11.00000 0.08045 0.03501 = 0.03605 0.00001 -0.01246 -0.00081 AFIX 43 H3 2 0.269194 0.372377 1.074461 11.00000 -1.20000 AFIX 0 C11 1 0.232432 0.435092 0.968023 11.00000 0.05635 0.03130 = 0.04408 -0.00101 -0.00353 0.00340 C12 1 0.117026 0.116179 0.926896 11.00000 0.04584 0.03987 = 0.03513 0.00245 -0.00466 -0.00003 C13 1 0.269130 -0.009108 0.920640 11.00000 0.05898 0.03227 = 0.04141 0.00035 -0.00342 0.00365 C14 1 0.193987 0.210473 0.931142 11.00000 0.04340 0.02990 = 0.03591 0.00108 -0.00059 0.00093 O1 4 0.083632 -0.012641 1.228118 11.00000 0.06727 0.08423 = 0.06834 0.02915 -0.00054 -0.01357 C16 1 0.071060 0.224093 0.740804 11.00000 0.06697 0.04603 = 0.04720 -0.00358 -0.00985 0.00543 AFIX 43 H16 2 0.005300 0.220030 0.769010 11.00000 -1.20000 AFIX 0 N1 3 0.187025 0.601475 0.717264 11.00000 0.07965 0.05179 = 0.06087 0.01837 -0.00223 0.00546 C18 1 0.130015 0.122400 1.126585 11.00000 0.04833 0.05148 = 0.04134 0.00212 -0.00321 0.00448 AFIX 43 H18 2 0.057675 0.131518 1.111187 11.00000 -1.20000 AFIX 0 N2 3 0.225410 0.657123 0.782072 11.00000 0.07225 0.04016 = 0.06739 0.01988 -0.00045 0.00300 AFIX 43 H2 2 0.243524 0.723591 0.779914 11.00000 -1.20000 AFIX 0 C20 1 0.232324 0.595934 0.851737 11.00000 0.05786 0.03569 = 0.05783 0.00800 0.00305 0.00649 N21 1 0.158035 0.048560 1.187606 11.00000 0.05354 0.04636 = 0.04253 0.00369 0.00044 -0.00203 N22 1 0.319125 0.169653 1.111835 11.00000 0.04954 0.03836 = 0.04359 0.00264 -0.00421 -0.00314 AFIX 43 H22 2 0.373269 0.210569 1.087091 11.00000 -1.20000 AFIX 0 N23 1 0.345446 0.094311 1.172799 11.00000 0.04832 0.04967 = 0.05099 0.00113 -0.01200 0.00198 AFIX 43 H23 2 0.417676 0.084738 1.188331 11.00000 -1.20000 AFIX 0 N24 1 0.196365 0.493456 0.830513 11.00000 0.05043 0.03561 = 0.04414 0.00582 0.00006 0.00514 C25 1 0.162836 0.261221 0.781104 11.00000 0.05863 0.03143 = 0.03789 0.00300 -0.00016 0.00443 C26 1 0.211642 0.181942 1.089281 11.00000 0.05228 0.03368 = 0.03539 -0.00132 -0.00073 0.00321 C27 1 0.262406 0.265598 0.739803 11.00000 0.07149 0.03961 = 0.05335 0.00663 0.01322 0.00421 AFIX 43 H27 2 0.325159 0.289302 0.766151 11.00000 -1.20000 AFIX 0 C28 1 0.168560 0.503945 0.745287 11.00000 0.06523 0.04598 = 0.05072 0.01385 -0.00628 0.00605 AFIX 43 H28 2 0.140732 0.448480 0.713403 11.00000 -1.20000 AFIX 0 C29 1 0.267178 0.621060 0.931389 11.00000 0.08445 0.02826 = 0.06375 -0.00082 -0.00398 -0.00105 AFIX 43 H29 2 0.288810 0.690022 0.945526 11.00000 -1.20000 AFIX 0 O2 4 0.354938 0.229748 0.610450 11.00000 0.13980 0.08931 = 0.10948 0.00462 0.06525 0.00072 C31 1 0.264580 0.232879 0.656846 11.00000 0.10923 0.05094 = 0.05469 0.01310 0.03479 0.01912 C32 1 0.457538 0.050644 0.921183 11.00000 0.04650 0.05699 = 0.11652 -0.02410 -0.01216 0.01474 AFIX 33 H32A 2 0.498841 0.115914 0.921423 11.00000 -1.50000 H32B 2 0.474873 0.009548 0.969363 11.00000 -1.50000 H32C 2 0.475235 0.009927 0.872888 11.00000 -1.50000 AFIX 0 C33 1 0.267931 0.539884 0.987166 11.00000 0.08304 0.03697 = 0.05038 -0.00464 -0.00264 0.00032 AFIX 43 H33 2 0.292844 0.553881 1.040132 11.00000 -1.20000 AFIX 0 C34 1 0.075689 0.192618 0.658385 11.00000 0.09260 0.05988 = 0.04772 -0.00460 -0.01247 0.01258 AFIX 43 H34 2 0.013283 0.168678 0.631693 11.00000 -1.20000 AFIX 0 C35 1 0.172304 0.197272 0.617443 11.00000 0.12494 0.05831 = 0.04277 -0.00502 -0.00016 0.01173 AFIX 43 H35 2 0.175920 0.176284 0.562598 11.00000 -1.20000 AFIX 0 C36 1 0.265035 0.034609 1.209662 11.00000 0.06233 0.04375 = 0.04533 0.00720 -0.00467 0.00402 AFIX 43 H36 2 0.283192 -0.015475 1.249736 11.00000 -1.20000 AFIX 0 C37 1 0.083645 -0.076864 0.923005 11.00000 0.07515 0.04291 = 0.08797 0.00327 -0.00678 -0.01723 AFIX 33 H37A 2 0.010252 -0.050484 0.924574 11.00000 -1.50000 H37B 2 0.094011 -0.118721 0.874073 11.00000 -1.50000 H37C 2 0.096898 -0.120666 0.970512 11.00000 -1.50000 AFIX 0 C38 1 -0.025595 -0.010311 1.199090 11.00000 0.06589 0.11546 = 0.09428 0.03485 -0.00379 -0.02849 AFIX 33 H38A 2 -0.069794 -0.056431 1.232531 11.00000 -1.50000 H38B 2 -0.053042 0.061565 1.202114 11.00000 -1.50000 H38C 2 -0.027674 -0.034496 1.143033 11.00000 -1.50000 AFIX 0 C39 1 0.448694 0.278251 0.645045 11.00000 0.14149 0.11476 = 0.20094 -0.03324 0.10394 -0.03130 AFIX 33 H39A 2 0.508540 0.271828 0.607363 11.00000 -1.50000 H39B 2 0.434315 0.352610 0.655390 11.00000 -1.50000 H39C 2 0.466731 0.243170 0.695816 11.00000 -1.50000 AFIX 0 HKLF 4 REM SIR97 run in space group P 21 21 21 REM wR2 = 0.1520, GooF = S = 1.075, Restrained GooF = 1.075 for all data REM R1 = 0.0517 for 4174 Fo > 4sig(Fo) and 0.0661 for all 5062 data REM 352 parameters refined using 0 restraints END WGHT 0.0804 0.6183 REM Highest difference peak 0.561, deepest hole -0.228, 1-sigma level 0.046 Q1 1 0.0048 0.1349 0.5426 11.00000 0.05 0.37 Q2 1 0.2155 -0.1084 0.9221 11.00000 0.05 0.20 Q3 1 0.0363 -0.0738 0.8691 11.00000 0.05 0.18 Q4 1 0.3028 0.3197 0.8603 11.00000 0.05 0.17 Q5 1 0.4964 0.0825 0.9815 11.00000 0.05 0.17 Q6 1 0.2749 0.4037 0.8826 11.00000 0.05 0.17 Q7 1 0.0728 0.1557 0.5743 11.00000 0.05 0.16 Q8 1 0.4582 -0.0394 0.9221 11.00000 0.05 0.16 Q9 1 0.0414 0.0970 1.0918 11.00000 0.05 0.14 Q10 1 0.4820 0.0966 0.8737 11.00000 0.05 0.14 Q11 1 0.3052 0.0320 0.9156 11.00000 0.05 0.14 Q12 1 0.2561 0.5165 0.7327 11.00000 0.05 0.13 Q13 1 0.4219 -0.0808 0.9283 11.00000 0.05 0.13 Q14 1 0.4784 0.0919 1.1310 11.00000 0.05 0.13 Q15 1 0.2034 -0.1099 1.2908 11.00000 0.05 0.13 Q16 1 0.0214 0.1111 1.1065 11.00000 0.05 0.13 Q17 1 0.3952 0.4113 0.9742 11.00000 0.05 0.13 Q18 1 0.3145 0.3592 1.0211 11.00000 0.05 0.13 Q19 1 0.2710 0.1629 1.0759 11.00000 0.05 0.13 Q20 1 0.1366 -0.1514 0.9193 11.00000 0.05 0.13 Q21 1 0.2377 0.4598 1.0919 11.00000 0.05 0.13 Q22 1 0.3222 -0.0593 1.2210 11.00000 0.05 0.13 Q23 1 0.2823 0.1336 0.7216 11.00000 0.05 0.12 Q24 1 0.0983 0.2342 0.9269 11.00000 0.05 0.12 Q25 1 0.2679 0.5934 0.7208 11.00000 0.05 0.12 ; _shelx_res_checksum 96368 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 N5 N 0.3414(3) 0.0758(2) 0.9210(2) 0.0464(8) Uani 1 1 d . . . . . O4 O 0.3009(3) -0.1011(2) 0.9175(2) 0.0668(9) Uani 1 1 d . . . . . O5 O 0.0192(2) 0.1299(2) 0.9299(2) 0.0539(7) Uani 1 1 d . . . . . O3 O 0.3821(2) 0.2513(2) 0.9138(2) 0.0545(7) Uani 1 1 d . . . . . N4 N 0.1603(3) 0.0145(2) 0.9228(2) 0.0441(7) Uani 1 1 d . . . . . C6 C 0.1783(3) 0.2590(3) 1.0216(2) 0.0398(8) Uani 1 1 d . . . . . H6 H 0.100418 0.273367 1.028734 0.048 Uiso 1 1 calc R U . . . C7 C 0.1961(3) 0.4093(3) 0.8895(2) 0.0408(8) Uani 1 1 d . . . . . C8 C 0.3120(3) 0.1832(3) 0.9201(2) 0.0393(8) Uani 1 1 d . . . . . C9 C 0.1528(3) 0.2978(3) 0.8702(2) 0.0379(8) Uani 1 1 d . . . . . H9 H 0.074209 0.302434 0.880227 0.045 Uiso 1 1 calc R U . . . N3 N 0.2339(3) 0.3591(2) 1.0299(2) 0.0505(8) Uani 1 1 d . . . . . H3 H 0.269194 0.372377 1.074461 0.061 Uiso 1 1 calc R U . . . C11 C 0.2324(3) 0.4351(3) 0.9680(2) 0.0439(9) Uani 1 1 d . . . . . C12 C 0.1170(3) 0.1162(3) 0.9269(2) 0.0403(8) Uani 1 1 d . . . . . C13 C 0.2691(3) -0.0091(3) 0.9206(2) 0.0442(8) Uani 1 1 d . . . . . C14 C 0.1940(3) 0.2105(3) 0.9311(2) 0.0364(7) Uani 1 1 d . . . . . O1 O 0.0836(3) -0.0126(3) 1.2281(2) 0.0733(10) Uani 1 1 d . . . . . C16 C 0.0711(4) 0.2241(3) 0.7408(3) 0.0534(10) Uani 1 1 d . . . . . H16 H 0.005300 0.220030 0.769010 0.064 Uiso 1 1 calc R U . . . N1 N 0.1870(3) 0.6015(3) 0.7173(3) 0.0641(10) Uani 1 1 d . . . . . C18 C 0.1300(3) 0.1224(3) 1.1266(2) 0.0470(9) Uani 1 1 d . . . . . H18 H 0.057675 0.131518 1.111187 0.056 Uiso 1 1 calc R U . . . N2 N 0.2254(3) 0.6571(3) 0.7821(2) 0.0599(10) Uani 1 1 d . . . . . H2 H 0.243524 0.723591 0.779914 0.072 Uiso 1 1 calc R U . . . C20 C 0.2323(4) 0.5959(3) 0.8517(3) 0.0505(10) Uani 1 1 d . . . . . N21 C 0.1580(3) 0.0486(3) 1.1876(2) 0.0475(9) Uani 1 1 d . . . . . N22 C 0.3191(3) 0.1697(3) 1.1118(2) 0.0438(9) Uani 1 1 d . . . . . H22 H 0.373269 0.210569 1.087091 0.053 Uiso 1 1 calc R U . . . N23 C 0.3454(3) 0.0943(3) 1.1728(3) 0.0497(9) Uani 1 1 d . . . . . H23 H 0.417676 0.084738 1.188331 0.060 Uiso 1 1 calc R U . . . N24 C 0.1964(3) 0.4935(3) 0.8305(2) 0.0434(8) Uani 1 1 d . . . . . C25 C 0.1628(3) 0.2612(3) 0.7811(2) 0.0426(8) Uani 1 1 d . . . . . C26 C 0.2116(3) 0.1819(3) 1.0893(2) 0.0405(8) Uani 1 1 d . . . . . C27 C 0.2624(4) 0.2656(3) 0.7398(3) 0.0548(10) Uani 1 1 d . . . . . H27 H 0.325159 0.289302 0.766151 0.066 Uiso 1 1 calc R U . . . C28 C 0.1686(4) 0.5039(3) 0.7453(3) 0.0540(10) Uani 1 1 d . . . . . H28 H 0.140732 0.448480 0.713403 0.065 Uiso 1 1 calc R U . . . C29 C 0.2672(4) 0.6211(3) 0.9314(3) 0.0588(11) Uani 1 1 d . . . . . H29 H 0.288810 0.690022 0.945526 0.071 Uiso 1 1 calc R U . . . O2 O 0.3549(5) 0.2297(4) 0.6105(3) 0.1129(17) Uani 1 1 d . . . . . C31 C 0.2646(5) 0.2329(4) 0.6568(3) 0.0716(15) Uani 1 1 d . . . . . C32 C 0.4575(4) 0.0506(4) 0.9212(4) 0.0733(15) Uani 1 1 d . . . . . H32A H 0.498841 0.115914 0.921423 0.110 Uiso 1 1 calc R U . . . H32B H 0.474873 0.009548 0.969363 0.110 Uiso 1 1 calc R U . . . H32C H 0.475235 0.009927 0.872888 0.110 Uiso 1 1 calc R U . . . C33 C 0.2679(4) 0.5399(3) 0.9872(3) 0.0568(11) Uani 1 1 d . . . . . H33 H 0.292844 0.553881 1.040132 0.068 Uiso 1 1 calc R U . . . C34 C 0.0757(5) 0.1926(4) 0.6584(3) 0.0667(13) Uani 1 1 d . . . . . H34 H 0.013283 0.168678 0.631693 0.080 Uiso 1 1 calc R U . . . C35 C 0.1723(6) 0.1973(4) 0.6174(3) 0.0753(15) Uani 1 1 d . . . . . H35 H 0.175920 0.176284 0.562598 0.090 Uiso 1 1 calc R U . . . C36 C 0.2650(4) 0.0346(3) 1.2097(3) 0.0505(10) Uani 1 1 d . . . . . H36 H 0.283192 -0.015475 1.249736 0.061 Uiso 1 1 calc R U . . . C37 C 0.0836(4) -0.0769(3) 0.9230(4) 0.0687(13) Uani 1 1 d . . . . . H37A H 0.010252 -0.050484 0.924574 0.103 Uiso 1 1 calc R U . . . H37B H 0.094011 -0.118721 0.874073 0.103 Uiso 1 1 calc R U . . . H37C H 0.096898 -0.120666 0.970512 0.103 Uiso 1 1 calc R U . . . C38 C -0.0256(5) -0.0103(6) 1.1991(4) 0.092(2) Uani 1 1 d . . . . . H38A H -0.069794 -0.056431 1.232531 0.138 Uiso 1 1 calc R U . . . H38B H -0.053042 0.061565 1.202114 0.138 Uiso 1 1 calc R U . . . H38C H -0.027674 -0.034496 1.143033 0.138 Uiso 1 1 calc R U . . . C39 C 0.4487(8) 0.2783(8) 0.6450(6) 0.152(4) Uani 1 1 d . . . . . H39A H 0.508540 0.271828 0.607363 0.229 Uiso 1 1 calc R U . . . H39B H 0.434315 0.352610 0.655390 0.229 Uiso 1 1 calc R U . . . H39C H 0.466731 0.243170 0.695816 0.229 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 N5 0.0435(17) 0.0419(16) 0.0539(19) -0.0110(15) -0.0047(15) 0.0039(13) O4 0.081(2) 0.0353(14) 0.084(2) -0.0001(15) -0.0061(19) 0.0108(15) O5 0.0415(15) 0.0547(15) 0.0655(19) 0.0063(14) 0.0006(13) -0.0027(13) O3 0.0478(15) 0.0457(14) 0.0700(19) 0.0020(14) -0.0020(14) -0.0072(13) N4 0.0507(18) 0.0336(14) 0.0481(18) 0.0008(14) -0.0018(15) -0.0070(13) C6 0.053(2) 0.0356(16) 0.0313(17) 0.0010(15) -0.0026(15) 0.0045(16) C7 0.049(2) 0.0303(16) 0.043(2) 0.0020(15) -0.0004(16) 0.0050(15) C8 0.0454(19) 0.0378(17) 0.0346(18) -0.0019(15) -0.0045(15) -0.0019(16) C9 0.0429(19) 0.0356(17) 0.0351(18) 0.0044(14) -0.0007(14) 0.0033(14) N3 0.080(2) 0.0350(15) 0.0361(16) 0.0000(13) -0.0125(16) -0.0008(16) C11 0.056(2) 0.0313(17) 0.044(2) -0.0010(15) -0.0035(17) 0.0034(16) C12 0.046(2) 0.0399(17) 0.0351(18) 0.0025(15) -0.0047(16) 0.0000(15) C13 0.059(2) 0.0323(16) 0.041(2) 0.0003(15) -0.0034(18) 0.0037(16) C14 0.0434(19) 0.0299(15) 0.0359(18) 0.0011(13) -0.0006(15) 0.0009(14) O1 0.067(2) 0.084(2) 0.068(2) 0.0291(19) -0.0005(17) -0.0136(18) C16 0.067(3) 0.046(2) 0.047(2) -0.0036(17) -0.0099(19) 0.0054(19) N1 0.080(3) 0.052(2) 0.061(2) 0.0184(19) -0.002(2) 0.005(2) C18 0.048(2) 0.051(2) 0.041(2) 0.0021(17) -0.0032(16) 0.0045(18) N2 0.072(2) 0.0402(17) 0.067(2) 0.0199(18) 0.000(2) 0.0030(17) C20 0.058(2) 0.0357(18) 0.058(2) 0.0080(17) 0.0031(19) 0.0065(18) N21 0.054(2) 0.046(2) 0.043(2) 0.0037(17) 0.0004(17) -0.0020(18) N22 0.050(2) 0.0384(18) 0.044(2) 0.0026(16) -0.0042(16) -0.0031(16) N23 0.048(2) 0.050(2) 0.051(2) 0.0011(18) -0.0120(18) 0.0020(18) N24 0.050(2) 0.0356(18) 0.044(2) 0.0058(15) 0.0001(16) 0.0051(17) C25 0.059(2) 0.0314(16) 0.0379(18) 0.0030(15) -0.0002(16) 0.0044(16) C26 0.052(2) 0.0337(16) 0.0354(18) -0.0013(14) -0.0007(15) 0.0032(15) C27 0.071(3) 0.0396(19) 0.053(2) 0.0066(18) 0.013(2) 0.0042(19) C28 0.065(3) 0.046(2) 0.051(2) 0.0138(18) -0.0063(19) 0.0060(19) C29 0.084(3) 0.0283(17) 0.064(3) -0.0008(18) -0.004(2) -0.0011(19) O2 0.140(4) 0.089(3) 0.109(3) 0.005(3) 0.065(3) 0.001(3) C31 0.109(4) 0.051(2) 0.055(3) 0.013(2) 0.035(3) 0.019(3) C32 0.047(2) 0.057(2) 0.117(4) -0.024(3) -0.012(3) 0.015(2) C33 0.083(3) 0.0370(19) 0.050(2) -0.0046(17) -0.003(2) 0.000(2) C34 0.093(4) 0.060(3) 0.048(3) -0.005(2) -0.012(2) 0.013(3) C35 0.125(5) 0.058(3) 0.043(2) -0.005(2) 0.000(3) 0.012(3) C36 0.062(3) 0.044(2) 0.045(2) 0.0072(17) -0.0047(19) 0.0040(19) C37 0.075(3) 0.043(2) 0.088(4) 0.003(2) -0.007(3) -0.017(2) C38 0.066(3) 0.115(5) 0.094(4) 0.035(4) -0.004(3) -0.028(3) C39 0.141(7) 0.115(6) 0.201(10) -0.033(7) 0.104(7) -0.031(6) 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 _geom_angle_publ_flag C13 N5 C8 125.0(3) . . ? C13 N5 C32 117.5(3) . . ? C8 N5 C32 117.5(3) . . ? C13 N4 C12 125.2(3) . . ? C13 N4 C37 117.1(3) . . ? C12 N4 C37 117.7(3) . . ? N3 C6 C26 110.9(3) . . ? N3 C6 C14 111.0(3) . . ? C26 C6 C14 113.1(3) . . ? N3 C6 H6 107.1 . . ? C26 C6 H6 107.1 . . ? C14 C6 H6 107.1 . . ? C11 C7 N24 116.5(3) . . ? C11 C7 C9 120.8(3) . . ? N24 C7 C9 122.6(3) . . ? O3 C8 N5 119.5(3) . . ? O3 C8 C14 122.4(3) . . ? N5 C8 C14 118.0(3) . . ? C7 C9 C25 116.2(3) . . ? C7 C9 C14 113.3(3) . . ? C25 C9 C14 111.6(3) . . ? C7 C9 H9 104.8 . . ? C25 C9 H9 104.8 . . ? C14 C9 H9 104.8 . . ? C11 N3 C6 121.7(3) . . ? C11 N3 H3 119.2 . . ? C6 N3 H3 119.2 . . ? N3 C11 C7 120.9(3) . . ? N3 C11 C33 118.1(3) . . ? C7 C11 C33 121.0(3) . . ? O5 C12 N4 120.9(3) . . ? O5 C12 C14 120.5(3) . . ? N4 C12 C14 118.6(3) . . ? O4 C13 N4 121.2(4) . . ? O4 C13 N5 121.3(4) . . ? N4 C13 N5 117.5(3) . . ? C8 C14 C12 114.9(3) . . ? C8 C14 C9 113.4(3) . . ? C12 C14 C9 108.2(3) . . ? C8 C14 C6 108.2(3) . . ? C12 C14 C6 105.1(3) . . ? C9 C14 C6 106.2(3) . . ? N21 O1 C38 117.5(4) . . ? C25 C16 C34 121.0(5) . . ? C25 C16 H16 119.5 . . ? C34 C16 H16 119.5 . . ? C28 N1 N2 105.5(4) . . ? C26 C18 N21 119.1(4) . . ? C26 C18 H18 120.5 . . ? N21 C18 H18 120.5 . . ? N1 N2 C20 112.4(3) . . ? N1 N2 H2 123.8 . . ? C20 N2 H2 123.8 . . ? N2 C20 N24 106.7(4) . . ? N2 C20 C29 131.2(4) . . ? N24 C20 C29 122.0(4) . . ? O1 N21 C36 116.4(4) . . ? O1 N21 C18 123.3(4) . . ? C36 N21 C18 120.3(4) . . ? C26 N22 N23 118.9(4) . . ? C26 N22 H22 120.6 . . ? N23 N22 H22 120.6 . . ? C36 N23 N22 120.4(4) . . ? C36 N23 H23 119.8 . . ? N22 N23 H23 119.8 . . ? C20 N24 C7 120.8(4) . . ? C20 N24 C28 103.3(3) . . ? C7 N24 C28 135.9(4) . . ? C16 C25 C27 119.9(4) . . ? C16 C25 C9 119.0(4) . . ? C27 C25 C9 121.1(4) . . ? N22 C26 C18 121.1(3) . . ? N22 C26 C6 121.4(3) . . ? C18 C26 C6 117.5(3) . . ? C25 C27 C31 117.7(5) . . ? C25 C27 H27 121.1 . . ? C31 C27 H27 121.1 . . ? N1 C28 N24 112.1(4) . . ? N1 C28 H28 123.9 . . ? N24 C28 H28 123.9 . . ? C33 C29 C20 116.8(4) . . ? C33 C29 H29 121.6 . . ? C20 C29 H29 121.6 . . ? C31 O2 C39 115.9(6) . . ? O2 C31 C35 114.2(5) . . ? O2 C31 C27 124.2(6) . . ? C35 C31 C27 121.6(5) . . ? N5 C32 H32A 109.5 . . ? N5 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N5 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C29 C33 C11 122.8(4) . . ? C29 C33 H33 118.6 . . ? C11 C33 H33 118.6 . . ? C35 C34 C16 119.5(5) . . ? C35 C34 H34 120.3 . . ? C16 C34 H34 120.3 . . ? C34 C35 C31 120.3(5) . . ? C34 C35 H35 119.9 . . ? C31 C35 H35 119.9 . . ? N21 C36 N23 120.3(4) . . ? N21 C36 H36 119.8 . . ? N23 C36 H36 119.8 . . ? N4 C37 H37A 109.5 . . ? N4 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? N4 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O1 C38 H38A 109.5 . . ? O1 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O1 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O2 C39 H39A 109.5 . . ? O2 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? O2 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? 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 N5 C13 1.383(5) . ? N5 C8 1.388(5) . ? N5 C32 1.461(5) . ? O4 C13 1.215(4) . ? O5 C12 1.215(5) . ? O3 C8 1.215(4) . ? N4 C13 1.369(5) . ? N4 C12 1.379(5) . ? N4 C37 1.479(5) . ? C6 N3 1.431(5) . ? C6 C26 1.517(5) . ? C6 C14 1.602(5) . ? C6 H6 0.9800 . ? C7 C11 1.390(5) . ? C7 N24 1.422(5) . ? C7 C9 1.523(5) . ? C8 C14 1.499(5) . ? C9 C25 1.523(5) . ? C9 C14 1.558(5) . ? C9 H9 0.9800 . ? N3 C11 1.382(5) . ? N3 H3 0.8600 . ? C11 C33 1.414(5) . ? C12 C14 1.511(5) . ? O1 N21 1.361(5) . ? O1 C38 1.422(7) . ? C16 C25 1.384(6) . ? C16 C34 1.397(6) . ? C16 H16 0.9300 . ? N1 C28 1.320(5) . ? N1 N2 1.347(6) . ? C18 C26 1.388(5) . ? C18 N21 1.397(6) . ? C18 H18 0.9300 . ? N2 C20 1.368(5) . ? N2 H2 0.8600 . ? C20 N24 1.397(5) . ? C20 C29 1.399(6) . ? N21 C36 1.373(6) . ? N22 C26 1.379(6) . ? N22 N23 1.404(5) . ? N22 H22 0.9300 . ? N23 C36 1.375(6) . ? N23 H23 0.9300 . ? N24 C28 1.432(6) . ? C25 C27 1.396(6) . ? C27 C31 1.409(6) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C33 1.360(6) . ? C29 H29 0.9300 . ? O2 C31 1.342(6) . ? O2 C39 1.417(11) . ? C31 C35 1.375(8) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33 0.9300 . ? C34 C35 1.362(8) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? 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 C13 N5 C8 O3 -174.1(4) . . . . ? C32 N5 C8 O3 5.0(6) . . . . ? C13 N5 C8 C14 8.9(5) . . . . ? C32 N5 C8 C14 -172.0(4) . . . . ? C11 C7 C9 C25 -153.6(4) . . . . ? N24 C7 C9 C25 29.8(5) . . . . ? C11 C7 C9 C14 -22.4(5) . . . . ? N24 C7 C9 C14 161.0(3) . . . . ? C26 C6 N3 C11 168.2(4) . . . . ? C14 C6 N3 C11 41.5(5) . . . . ? C6 N3 C11 C7 -13.2(6) . . . . ? C6 N3 C11 C33 166.2(4) . . . . ? N24 C7 C11 N3 179.2(4) . . . . ? C9 C7 C11 N3 2.4(6) . . . . ? N24 C7 C11 C33 -0.2(6) . . . . ? C9 C7 C11 C33 -177.0(4) . . . . ? C13 N4 C12 O5 -178.8(4) . . . . ? C37 N4 C12 O5 -0.6(6) . . . . ? C13 N4 C12 C14 -1.3(6) . . . . ? C37 N4 C12 C14 176.9(4) . . . . ? C12 N4 C13 O4 179.6(4) . . . . ? C37 N4 C13 O4 1.3(6) . . . . ? C12 N4 C13 N5 -1.3(6) . . . . ? C37 N4 C13 N5 -179.6(4) . . . . ? C8 N5 C13 O4 176.4(4) . . . . ? C32 N5 C13 O4 -2.7(6) . . . . ? C8 N5 C13 N4 -2.7(6) . . . . ? C32 N5 C13 N4 178.2(4) . . . . ? O3 C8 C14 C12 172.6(3) . . . . ? N5 C8 C14 C12 -10.5(5) . . . . ? O3 C8 C14 C9 47.3(5) . . . . ? N5 C8 C14 C9 -135.8(3) . . . . ? O3 C8 C14 C6 -70.3(4) . . . . ? N5 C8 C14 C6 106.6(3) . . . . ? O5 C12 C14 C8 -175.4(3) . . . . ? N4 C12 C14 C8 7.1(5) . . . . ? O5 C12 C14 C9 -47.5(5) . . . . ? N4 C12 C14 C9 135.0(3) . . . . ? O5 C12 C14 C6 65.8(4) . . . . ? N4 C12 C14 C6 -111.8(4) . . . . ? C7 C9 C14 C8 -71.9(4) . . . . ? C25 C9 C14 C8 61.5(4) . . . . ? C7 C9 C14 C12 159.3(3) . . . . ? C25 C9 C14 C12 -67.3(4) . . . . ? C7 C9 C14 C6 46.8(4) . . . . ? C25 C9 C14 C6 -179.8(3) . . . . ? N3 C6 C14 C8 65.8(4) . . . . ? C26 C6 C14 C8 -59.7(4) . . . . ? N3 C6 C14 C12 -170.9(3) . . . . ? C26 C6 C14 C12 63.6(4) . . . . ? N3 C6 C14 C9 -56.3(4) . . . . ? C26 C6 C14 C9 178.2(3) . . . . ? C28 N1 N2 C20 0.3(5) . . . . ? N1 N2 C20 N24 0.3(5) . . . . ? N1 N2 C20 C29 -180.0(5) . . . . ? C38 O1 N21 C36 -171.8(5) . . . . ? C38 O1 N21 C18 8.2(7) . . . . ? C26 C18 N21 O1 179.4(4) . . . . ? C26 C18 N21 C36 -0.6(6) . . . . ? C26 N22 N23 C36 -0.5(6) . . . . ? N2 C20 N24 C7 178.4(4) . . . . ? C29 C20 N24 C7 -1.3(6) . . . . ? N2 C20 N24 C28 -0.6(5) . . . . ? C29 C20 N24 C28 179.6(4) . . . . ? C11 C7 N24 C20 0.4(6) . . . . ? C9 C7 N24 C20 177.1(4) . . . . ? C11 C7 N24 C28 179.1(5) . . . . ? C9 C7 N24 C28 -4.2(7) . . . . ? C34 C16 C25 C27 -1.3(6) . . . . ? C34 C16 C25 C9 178.1(4) . . . . ? C7 C9 C25 C16 -127.2(4) . . . . ? C14 C9 C25 C16 100.8(4) . . . . ? C7 C9 C25 C27 52.2(5) . . . . ? C14 C9 C25 C27 -79.7(4) . . . . ? N23 N22 C26 C18 0.9(6) . . . . ? N23 N22 C26 C6 -177.7(3) . . . . ? N21 C18 C26 N22 -0.4(6) . . . . ? N21 C18 C26 C6 178.3(3) . . . . ? N3 C6 C26 N22 -44.2(5) . . . . ? C14 C6 C26 N22 81.3(4) . . . . ? N3 C6 C26 C18 137.1(4) . . . . ? C14 C6 C26 C18 -97.3(4) . . . . ? C16 C25 C27 C31 1.0(6) . . . . ? C9 C25 C27 C31 -178.4(3) . . . . ? N2 N1 C28 N24 -0.7(5) . . . . ? C20 N24 C28 N1 0.9(5) . . . . ? C7 N24 C28 N1 -178.0(5) . . . . ? N2 C20 C29 C33 -177.6(5) . . . . ? N24 C20 C29 C33 2.1(7) . . . . ? C39 O2 C31 C35 172.3(6) . . . . ? C39 O2 C31 C27 -10.0(9) . . . . ? C25 C27 C31 O2 -177.9(4) . . . . ? C25 C27 C31 C35 -0.3(6) . . . . ? C20 C29 C33 C11 -1.9(7) . . . . ? N3 C11 C33 C29 -178.4(4) . . . . ? C7 C11 C33 C29 1.0(7) . . . . ? C25 C16 C34 C35 0.9(7) . . . . ? C16 C34 C35 C31 -0.1(7) . . . . ? O2 C31 C35 C34 177.7(5) . . . . ? C27 C31 C35 C34 -0.1(8) . . . . ? O1 N21 C36 N23 -179.0(4) . . . . ? C18 N21 C36 N23 1.0(7) . . . . ? N22 N23 C36 N21 -0.4(6) . . . . ?