#------------------------------------------------------------------------------ #$Date: 2020-05-23 07:18:32 +0300 (Sat, 23 May 2020) $ #$Revision: 252308 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240581.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_7240581 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_formula_moiety 'C27 H21 CL2 N5 O3' _chemical_formula_sum 'C27 H21 Cl2 N5 O3' _chemical_formula_weight 534.39 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-01-16 deposited with the CCDC. 2020-05-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.750(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.6991(4) _cell_length_b 15.1736(7) _cell_length_c 18.5825(9) _cell_measurement_reflns_used 4865 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.1 _cell_measurement_theta_min 2.1 _cell_volume 2677.5(2) _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 'ORTEP3 MERCURY AND PLATON' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (SHELDRICK,2018)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'BRUKER D8 VENTURE,PHOTON-200' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_unetI/netI 0.0183 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 32350 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.098 _diffrn_reflns_theta_min 2.145 _diffrn_source 'FINE FOCUS SEALED TUBE' _exptl_absorpt_coefficient_mu 0.280 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS-2016/2 _exptl_crystal_colour COLURLESS _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_meas 1.3 _exptl_crystal_density_method 'NOT MEASURED' _exptl_crystal_description 'BLOCK TYPE' _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.456 _exptl_crystal_size_mid 0.359 _exptl_crystal_size_min 0.348 _exptl_transmission_factor_max 0.7455 _exptl_transmission_factor_min 0.5925 _refine_diff_density_max 7.932 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.200 _refine_ls_extinction_coef 0.000(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 2.792 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 335 _refine_ls_number_reflns 5870 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 2.792 _refine_ls_R_factor_all 0.1904 _refine_ls_R_factor_gt 0.1802 _refine_ls_shift/su_max 0.593 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.5419 _refine_ls_wR_factor_ref 0.5603 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4865 _reflns_number_total 5870 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02990d2.cif _cod_data_source_block shelx_CCDC1 _cod_depositor_comments ; The following automatic conversions were performed: 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_sg_symbol_H-M 'P 21/c' _cod_database_code 7240581 _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 DB_1 in P2(1)/c shelx.res created by SHELXL-2018/3 at 15:45:55 on 16-Jan-2020 CELL 0.71073 9.6991 15.1736 18.5825 90.000 101.750 90.000 ZERR 4.00 0.0004 0.0007 0.0009 0.000 0.002 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O CL UNIT 108 84 20 12 8 MERG 2 FMAP 2 PLAN 20 ACTA BOND L.S. 4 TEMP 20.00 WGHT 0.200000 EXTI 0.000000 FVAR 2.48006 MOLE 1 CL1 5 0.570792 0.726190 0.119359 11.00000 0.03446 0.15440 = 0.06424 -0.02092 -0.00915 0.02491 CL2 5 1.729620 1.060655 0.448232 11.00000 0.09047 0.06324 = 0.10163 -0.02045 0.01103 -0.04145 O1 4 1.218265 0.742863 0.403399 11.00000 0.04194 0.04813 = 0.03700 0.01229 0.01034 0.00331 C9 1 1.189185 0.782132 0.345173 11.00000 0.02443 0.03021 = 0.03850 0.00660 0.00233 -0.00263 C7 1 1.417511 0.741524 0.304843 11.00000 0.02307 0.03188 = 0.03555 0.00215 0.00472 0.00052 AFIX 13 H7 2 1.451996 0.734988 0.259089 11.00000 -1.20000 AFIX 0 C8 1 1.255615 0.758705 0.280936 11.00000 0.02655 0.03226 = 0.03510 0.00378 -0.00032 0.00766 C6 1 1.494227 0.821901 0.343685 11.00000 0.02951 0.02859 = 0.03903 0.00701 0.00501 -0.00094 O3 4 1.294488 0.821788 0.169512 11.00000 0.05085 0.07066 = 0.04126 0.01905 0.01520 0.01146 N1 3 1.086814 0.846552 0.334725 11.00000 0.03694 0.03853 = 0.04486 -0.00277 0.01334 0.00753 C24 1 1.613103 0.550960 0.422557 11.00000 0.03059 0.03925 = 0.03937 0.00655 0.00581 0.01022 N3 3 1.213915 0.600523 0.297986 11.00000 0.03451 0.03001 = 0.05376 0.00043 -0.00472 -0.00205 AFIX 43 H3 2 1.146047 0.568287 0.306462 11.00000 -1.20000 AFIX 0 C20 1 1.188099 0.669165 0.244194 11.00000 0.03284 0.03234 = 0.03956 -0.00334 0.00179 0.00328 AFIX 13 H20 2 1.235411 0.653654 0.204097 11.00000 -1.20000 AFIX 0 C19 1 1.032046 0.679373 0.212494 11.00000 0.03128 0.03723 = 0.03515 -0.00798 -0.00065 -0.00016 O2 4 0.948471 0.944955 0.263521 11.00000 0.06789 0.07385 = 0.08319 0.02871 0.02247 0.04523 N5 3 1.748446 0.551712 0.459963 11.00000 0.03407 0.05085 = 0.04312 0.01331 0.00482 0.01620 AFIX 43 H5 2 1.788839 0.508124 0.485446 11.00000 -1.20000 AFIX 0 N2 3 1.125176 0.885932 0.217298 11.00000 0.04755 0.03942 = 0.04677 0.01562 0.00978 0.01245 C27 1 1.449613 0.654928 0.345279 11.00000 0.03054 0.02863 = 0.03208 0.00011 0.00403 -0.00021 C1 1 1.507500 0.837945 0.418022 11.00000 0.04221 0.03459 = 0.04495 0.00367 0.01269 -0.00730 AFIX 43 H1 2 1.469480 0.798357 0.446878 11.00000 -1.20000 AFIX 0 C22 1 1.384134 0.502891 0.371107 11.00000 0.03795 0.03058 = 0.05217 0.00340 0.00442 -0.00215 AFIX 43 H22 2 1.315181 0.459366 0.364007 11.00000 -1.20000 AFIX 0 C25 1 1.716361 0.679673 0.408484 11.00000 0.02590 0.04084 = 0.04323 0.00205 0.00086 -0.00046 AFIX 43 H25 2 1.733994 0.736158 0.393147 11.00000 -1.20000 AFIX 0 C16 1 0.749956 0.706753 0.153990 11.00000 0.03120 0.08621 = 0.04755 -0.00969 -0.00242 0.00490 C3 1 1.635218 0.969285 0.408073 11.00000 0.05032 0.03784 = 0.06600 -0.00289 -0.00053 -0.01560 C21 1 1.352449 0.586880 0.336671 11.00000 0.03222 0.02837 = 0.04212 -0.00119 -0.00082 0.00147 N4 3 1.811837 0.628888 0.452376 11.00000 0.02997 0.05713 = 0.04405 0.00778 0.00023 0.00426 C11 1 1.046967 0.894669 0.271769 11.00000 0.04335 0.03638 = 0.05516 0.00502 0.00604 0.00974 C13 1 1.232309 0.825083 0.218201 11.00000 0.02729 0.04238 = 0.03902 0.00637 0.00497 0.00416 C26 1 1.585020 0.635489 0.388696 11.00000 0.02356 0.03215 = 0.03516 0.00624 0.00310 0.00223 C5 1 1.552995 0.881455 0.301413 11.00000 0.04661 0.04527 = 0.04226 0.00447 0.01447 -0.01656 AFIX 43 H5A 2 1.543536 0.871472 0.251266 11.00000 -1.20000 AFIX 0 C23 1 1.511867 0.485030 0.413784 11.00000 0.04935 0.02858 = 0.05055 0.00670 0.00791 0.01019 AFIX 43 H23 2 1.531018 0.430469 0.436411 11.00000 -1.20000 AFIX 0 C18 1 0.933249 0.668361 0.255671 11.00000 0.03947 0.05298 = 0.04067 -0.00499 -0.00162 -0.00026 AFIX 43 H18 2 0.962090 0.652041 0.304670 11.00000 -1.20000 AFIX 0 C2 1 1.577023 0.912565 0.449997 11.00000 0.04909 0.04976 = 0.04827 -0.00929 0.00127 -0.01082 AFIX 43 H2 2 1.583723 0.923661 0.499810 11.00000 -1.20000 AFIX 0 C14 1 0.984724 0.702133 0.138453 11.00000 0.03723 0.07380 = 0.03578 -0.00134 -0.00058 0.01062 AFIX 43 H14 2 1.049691 0.707385 0.108154 11.00000 -1.20000 AFIX 0 C4 1 1.625910 0.955933 0.333025 11.00000 0.05487 0.04365 = 0.06593 0.00631 0.01514 -0.01813 AFIX 43 H4 2 1.666708 0.995131 0.305026 11.00000 -1.20000 AFIX 0 C15 1 0.843651 0.716958 0.109429 11.00000 0.04288 0.08011 = 0.03694 -0.00318 -0.00348 0.01077 AFIX 43 H15 2 0.813720 0.733521 0.060555 11.00000 -1.20000 AFIX 0 C17 1 0.789379 0.681589 0.226255 11.00000 0.03227 0.07550 = 0.05008 -0.01437 0.00101 -0.00557 AFIX 43 H17 2 0.722429 0.673489 0.255062 11.00000 -1.20000 AFIX 0 C10 1 1.008690 0.860982 0.393511 11.00000 0.05404 0.07886 = 0.05065 -0.00716 0.02005 0.01476 AFIX 33 H10A 2 1.046247 0.823659 0.434541 11.00000 -1.50000 H10B 2 1.017608 0.921523 0.408754 11.00000 -1.50000 H10C 2 0.911098 0.847205 0.375703 11.00000 -1.50000 AFIX 0 C12 1 1.085468 0.940910 0.151634 11.00000 0.07561 0.08169 = 0.07212 0.04275 0.02225 0.03023 AFIX 33 H12A 2 1.010821 0.980047 0.157574 11.00000 -1.50000 H12B 2 1.165426 0.974728 0.144743 11.00000 -1.50000 H12C 2 1.054110 0.904018 0.109511 11.00000 -1.50000 AFIX 0 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM DB_1 in P2(1)/c REM wR2 = 0.5603, GooF = S = 2.792, Restrained GooF = 2.792 for all data REM R1 = 0.1802 for 4865 Fo > 4sig(Fo) and 0.1904 for all 5870 data REM 335 parameters refined using 0 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 7.932, deepest hole -0.650, 1-sigma level 0.200 Q1 1 1.8944 0.4092 0.5345 11.00000 0.05 7.93 Q2 1 0.5696 0.6656 0.1263 11.00000 0.05 0.62 Q3 1 1.5861 0.9048 0.3135 11.00000 0.05 0.58 Q4 1 1.0133 0.6813 0.1491 11.00000 0.05 0.51 Q5 1 1.7828 1.0245 0.4715 11.00000 0.05 0.50 Q6 1 1.1431 0.9629 0.1581 11.00000 0.05 0.46 Q7 1 1.5918 0.6143 0.4014 11.00000 0.05 0.44 Q8 1 1.7458 1.0362 0.4823 11.00000 0.05 0.43 Q9 1 0.8589 0.6782 0.1137 11.00000 0.05 0.37 Q10 1 0.8213 0.7897 0.0495 11.00000 0.05 0.36 Q11 1 1.4465 0.9054 0.1641 11.00000 0.05 0.36 Q12 1 1.1768 0.5508 0.2733 11.00000 0.05 0.36 Q13 1 1.1552 0.9138 0.1172 11.00000 0.05 0.35 Q14 1 0.8402 0.6627 0.1231 11.00000 0.05 0.35 Q15 1 1.1096 1.0243 0.1603 11.00000 0.05 0.33 Q16 1 0.9582 0.8001 0.4005 11.00000 0.05 0.32 Q17 1 1.6209 0.9008 0.6006 11.00000 0.05 0.31 Q18 1 1.6473 0.6607 0.3974 11.00000 0.05 0.31 Q19 1 1.1065 0.8973 0.4612 11.00000 0.05 0.30 Q20 1 1.0062 0.8022 0.0465 11.00000 0.05 0.29 ; _shelx_res_checksum 81970 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.57079(16) 0.7262(2) 0.11936(11) 0.0871(10) Uani 1 1 d . . . . . Cl2 Cl 1.7296(3) 1.06066(14) 0.44823(14) 0.0863(9) Uani 1 1 d . . . . . O1 O 1.2183(4) 0.7429(3) 0.4034(2) 0.0420(10) Uani 1 1 d . . . . . C9 C 1.1892(5) 0.7821(3) 0.3452(3) 0.0316(11) Uani 1 1 d . . . . . C7 C 1.4175(4) 0.7415(3) 0.3048(3) 0.0303(11) Uani 1 1 d . . . . . H7 H 1.451996 0.734988 0.259089 0.036 Uiso 1 1 calc R U . . . C8 C 1.2556(5) 0.7587(3) 0.2809(3) 0.0322(11) Uani 1 1 d . . . . . C6 C 1.4942(5) 0.8219(3) 0.3437(3) 0.0327(11) Uani 1 1 d . . . . . O3 O 1.2945(4) 0.8218(3) 0.1695(2) 0.0534(12) Uani 1 1 d . . . . . N1 N 1.0868(4) 0.8466(3) 0.3347(3) 0.0394(11) Uani 1 1 d . . . . . C24 C 1.6131(5) 0.5510(3) 0.4226(3) 0.0366(12) Uani 1 1 d . . . . . N3 N 1.2139(5) 0.6005(3) 0.2980(3) 0.0414(11) Uani 1 1 d . . . . . H3 H 1.146047 0.568287 0.306462 0.050 Uiso 1 1 calc R U . . . C20 C 1.1881(5) 0.6692(3) 0.2442(3) 0.0357(11) Uani 1 1 d . . . . . H20 H 1.235411 0.653654 0.204097 0.043 Uiso 1 1 calc R U . . . C19 C 1.0320(5) 0.6794(3) 0.2125(3) 0.0356(11) Uani 1 1 d . . . . . O2 O 0.9485(6) 0.9450(4) 0.2635(3) 0.0740(17) Uani 1 1 d . . . . . N5 N 1.7484(5) 0.5517(3) 0.4600(3) 0.0431(12) Uani 1 1 d . . . . . H5 H 1.788839 0.508124 0.485446 0.052 Uiso 1 1 calc R U . . . N2 N 1.1252(5) 0.8859(3) 0.2173(3) 0.0446(12) Uani 1 1 d . . . . . C27 C 1.4496(5) 0.6549(3) 0.3453(3) 0.0307(10) Uani 1 1 d . . . . . C1 C 1.5075(5) 0.8379(3) 0.4180(3) 0.0400(12) Uani 1 1 d . . . . . H1 H 1.469480 0.798357 0.446878 0.048 Uiso 1 1 calc R U . . . C22 C 1.3841(6) 0.5029(3) 0.3711(3) 0.0409(12) Uani 1 1 d . . . . . H22 H 1.315181 0.459366 0.364007 0.049 Uiso 1 1 calc R U . . . C25 C 1.7164(5) 0.6797(4) 0.4085(3) 0.0375(12) Uani 1 1 d . . . . . H25 H 1.733994 0.736158 0.393147 0.045 Uiso 1 1 calc R U . . . C16 C 0.7500(6) 0.7068(5) 0.1540(4) 0.0565(17) Uani 1 1 d . . . . . C3 C 1.6352(7) 0.9693(4) 0.4081(4) 0.0531(15) Uani 1 1 d . . . . . C21 C 1.3524(5) 0.5869(3) 0.3367(3) 0.0354(11) Uani 1 1 d . . . . . N4 N 1.8118(4) 0.6289(3) 0.4524(3) 0.0448(12) Uani 1 1 d . . . . . C11 C 1.0470(6) 0.8947(4) 0.2718(3) 0.0455(14) Uani 1 1 d . . . . . C13 C 1.2323(5) 0.8251(4) 0.2182(3) 0.0365(12) Uani 1 1 d . . . . . C26 C 1.5850(4) 0.6355(3) 0.3887(3) 0.0307(11) Uani 1 1 d . . . . . C5 C 1.5530(6) 0.8815(4) 0.3014(3) 0.0439(13) Uani 1 1 d . . . . . H5A H 1.543536 0.871472 0.251266 0.053 Uiso 1 1 calc R U . . . C23 C 1.5119(6) 0.4850(3) 0.4138(3) 0.0431(13) Uani 1 1 d . . . . . H23 H 1.531018 0.430469 0.436411 0.052 Uiso 1 1 calc R U . . . C18 C 0.9332(6) 0.6684(4) 0.2557(3) 0.0458(13) Uani 1 1 d . . . . . H18 H 0.962090 0.652041 0.304670 0.055 Uiso 1 1 calc R U . . . C2 C 1.5770(6) 0.9126(4) 0.4500(4) 0.0503(14) Uani 1 1 d . . . . . H2 H 1.583723 0.923661 0.499810 0.060 Uiso 1 1 calc R U . . . C14 C 0.9847(6) 0.7021(5) 0.1385(3) 0.0501(15) Uani 1 1 d . . . . . H14 H 1.049691 0.707385 0.108154 0.060 Uiso 1 1 calc R U . . . C4 C 1.6259(7) 0.9559(4) 0.3330(4) 0.0544(16) Uani 1 1 d . . . . . H4 H 1.666708 0.995131 0.305026 0.065 Uiso 1 1 calc R U . . . C15 C 0.8437(6) 0.7170(5) 0.1094(3) 0.0550(16) Uani 1 1 d . . . . . H15 H 0.813720 0.733521 0.060555 0.066 Uiso 1 1 calc R U . . . C17 C 0.7894(6) 0.6816(5) 0.2263(4) 0.0537(16) Uani 1 1 d . . . . . H17 H 0.722429 0.673489 0.255062 0.064 Uiso 1 1 calc R U . . . C10 C 1.0087(7) 0.8610(5) 0.3935(4) 0.0599(17) Uani 1 1 d . . . . . H10A H 1.046247 0.823659 0.434541 0.090 Uiso 1 1 calc R U . . . H10B H 1.017608 0.921523 0.408754 0.090 Uiso 1 1 calc R U . . . H10C H 0.911098 0.847205 0.375703 0.090 Uiso 1 1 calc R U . . . C12 C 1.0855(9) 0.9409(6) 0.1516(5) 0.075(2) Uani 1 1 d . . . . . H12A H 1.010821 0.980047 0.157574 0.113 Uiso 1 1 calc R U . . . H12B H 1.165426 0.974728 0.144743 0.113 Uiso 1 1 calc R U . . . H12C H 1.054110 0.904018 0.109511 0.113 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 Cl1 0.0345(10) 0.154(2) 0.0642(13) -0.0209(12) -0.0091(8) 0.0249(10) Cl2 0.0905(16) 0.0632(13) 0.1016(18) -0.0205(10) 0.0110(12) -0.0414(10) O1 0.042(2) 0.048(2) 0.037(2) 0.0123(15) 0.0103(16) 0.0033(15) C9 0.024(2) 0.030(2) 0.039(3) 0.0066(18) 0.0023(18) -0.0026(16) C7 0.023(2) 0.032(2) 0.036(2) 0.0022(17) 0.0047(17) 0.0005(16) C8 0.027(2) 0.032(2) 0.035(3) 0.0038(17) -0.0003(18) 0.0077(16) C6 0.030(2) 0.029(2) 0.039(3) 0.0070(18) 0.0050(18) -0.0009(17) O3 0.051(2) 0.071(3) 0.041(2) 0.0190(19) 0.0152(18) 0.011(2) N1 0.037(2) 0.039(2) 0.045(3) -0.0028(18) 0.0133(18) 0.0075(17) C24 0.031(2) 0.039(3) 0.039(3) 0.0065(19) 0.0058(19) 0.0102(19) N3 0.035(2) 0.030(2) 0.054(3) 0.0004(17) -0.0047(18) -0.0020(16) C20 0.033(2) 0.032(2) 0.040(3) -0.0033(18) 0.0018(19) 0.0033(18) C19 0.031(2) 0.037(2) 0.035(3) -0.0080(19) -0.0006(19) -0.0002(18) O2 0.068(3) 0.074(3) 0.083(4) 0.029(3) 0.022(3) 0.045(3) N5 0.034(2) 0.051(3) 0.043(2) 0.013(2) 0.0048(18) 0.0162(19) N2 0.048(3) 0.039(2) 0.047(3) 0.0156(19) 0.010(2) 0.0125(19) C27 0.031(2) 0.029(2) 0.032(2) 0.0001(16) 0.0040(17) -0.0002(17) C1 0.042(3) 0.035(2) 0.045(3) 0.004(2) 0.013(2) -0.007(2) C22 0.038(2) 0.031(2) 0.052(3) 0.003(2) 0.004(2) -0.0021(19) C25 0.026(2) 0.041(3) 0.043(3) 0.002(2) 0.0009(19) -0.0005(18) C16 0.031(3) 0.086(5) 0.048(3) -0.010(3) -0.002(2) 0.005(3) C3 0.050(3) 0.038(3) 0.066(4) -0.003(3) -0.001(3) -0.016(2) C21 0.032(2) 0.028(2) 0.042(3) -0.0012(18) -0.0008(19) 0.0015(18) N4 0.030(2) 0.057(3) 0.044(3) 0.008(2) 0.0002(18) 0.0043(19) C11 0.043(3) 0.036(3) 0.055(3) 0.005(2) 0.006(2) 0.010(2) C13 0.027(2) 0.042(3) 0.039(3) 0.006(2) 0.0050(19) 0.0042(18) C26 0.024(2) 0.032(2) 0.035(2) 0.0062(18) 0.0031(17) 0.0022(17) C5 0.047(3) 0.045(3) 0.042(3) 0.004(2) 0.014(2) -0.017(2) C23 0.049(3) 0.029(2) 0.051(3) 0.007(2) 0.008(2) 0.010(2) C18 0.039(3) 0.053(3) 0.041(3) -0.005(2) -0.002(2) 0.000(2) C2 0.049(3) 0.050(3) 0.048(3) -0.009(2) 0.001(2) -0.011(3) C14 0.037(3) 0.074(4) 0.036(3) -0.001(3) -0.001(2) 0.011(3) C4 0.055(3) 0.044(3) 0.066(4) 0.006(3) 0.015(3) -0.018(3) C15 0.043(3) 0.080(4) 0.037(3) -0.003(3) -0.003(2) 0.011(3) C17 0.032(3) 0.075(4) 0.050(3) -0.014(3) 0.001(2) -0.006(3) C10 0.054(3) 0.079(4) 0.051(4) -0.007(3) 0.020(3) 0.015(3) C12 0.076(5) 0.082(5) 0.072(5) 0.043(4) 0.022(4) 0.030(4) 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' Cl Cl 0.1484 0.1585 '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 O1 C9 N1 120.1(5) . . ? O1 C9 C8 121.9(4) . . ? N1 C9 C8 117.8(4) . . ? C27 C7 C6 115.2(4) . . ? C27 C7 C8 112.2(4) . . ? C6 C7 C8 111.4(4) . . ? C9 C8 C13 115.4(4) . . ? C9 C8 C7 112.3(4) . . ? C13 C8 C7 108.2(4) . . ? C9 C8 C20 109.5(4) . . ? C13 C8 C20 104.5(4) . . ? C7 C8 C20 106.2(4) . . ? C1 C6 C5 118.9(5) . . ? C1 C6 C7 123.3(4) . . ? C5 C6 C7 117.8(5) . . ? C11 N1 C9 124.7(5) . . ? C11 N1 C10 117.3(5) . . ? C9 N1 C10 117.9(5) . . ? N5 C24 C23 130.9(5) . . ? N5 C24 C26 107.2(4) . . ? C23 C24 C26 121.9(4) . . ? C21 N3 C20 118.6(4) . . ? N3 C20 C19 111.4(4) . . ? N3 C20 C8 108.8(4) . . ? C19 C20 C8 111.6(4) . . ? C18 C19 C14 118.2(5) . . ? C18 C19 C20 121.2(5) . . ? C14 C19 C20 120.5(5) . . ? N4 N5 C24 111.7(4) . . ? C13 N2 C11 125.0(4) . . ? C13 N2 C12 117.3(5) . . ? C11 N2 C12 117.6(5) . . ? C21 C27 C26 116.0(4) . . ? C21 C27 C7 121.6(4) . . ? C26 C27 C7 122.2(4) . . ? C6 C1 C2 120.6(5) . . ? C23 C22 C21 121.8(5) . . ? N4 C25 C26 110.9(5) . . ? C15 C16 C17 122.7(5) . . ? C15 C16 Cl1 119.6(5) . . ? C17 C16 Cl1 117.7(5) . . ? C2 C3 C4 122.1(5) . . ? C2 C3 Cl2 120.1(5) . . ? C4 C3 Cl2 117.7(5) . . ? C27 C21 N3 120.5(4) . . ? C27 C21 C22 122.2(4) . . ? N3 C21 C22 117.1(4) . . ? N5 N4 C25 106.8(4) . . ? O2 C11 N1 121.7(6) . . ? O2 C11 N2 120.2(5) . . ? N1 C11 N2 118.1(4) . . ? O3 C13 N2 121.0(5) . . ? O3 C13 C8 122.5(5) . . ? N2 C13 C8 116.3(4) . . ? C25 C26 C27 136.3(4) . . ? C25 C26 C24 103.2(4) . . ? C27 C26 C24 120.4(4) . . ? C6 C5 C4 121.2(5) . . ? C22 C23 C24 117.7(5) . . ? C19 C18 C17 120.6(5) . . ? C3 C2 C1 119.6(6) . . ? C15 C14 C19 121.5(6) . . ? C3 C4 C5 117.5(5) . . ? C16 C15 C14 118.4(6) . . ? C16 C17 C18 118.5(6) . . ? 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 Cl1 C16 1.751(6) . ? Cl2 C3 1.743(6) . ? O1 C9 1.217(6) . ? C9 N1 1.379(6) . ? C9 C8 1.510(7) . ? C7 C27 1.514(6) . ? C7 C6 1.531(6) . ? C7 C8 1.564(6) . ? C8 C13 1.522(7) . ? C8 C20 1.600(7) . ? C6 C1 1.383(7) . ? C6 C5 1.393(7) . ? O3 C13 1.186(7) . ? N1 C11 1.366(7) . ? N1 C10 1.467(8) . ? C24 N5 1.355(7) . ? C24 C23 1.388(8) . ? C24 C26 1.430(6) . ? N3 C21 1.404(6) . ? N3 C20 1.430(7) . ? C20 C19 1.516(6) . ? C19 C18 1.379(8) . ? C19 C14 1.402(8) . ? O2 C11 1.208(7) . ? N5 N4 1.343(7) . ? N2 C13 1.388(7) . ? N2 C11 1.389(8) . ? N2 C12 1.463(8) . ? C27 C21 1.385(7) . ? C27 C26 1.425(6) . ? C1 C2 1.388(7) . ? C22 C23 1.355(8) . ? C22 C21 1.431(7) . ? C25 N4 1.345(6) . ? C25 C26 1.420(6) . ? C16 C15 1.357(10) . ? C16 C17 1.373(10) . ? C3 C2 1.358(9) . ? C3 C4 1.394(10) . ? C5 C4 1.398(8) . ? C18 C17 1.406(8) . ? C14 C15 1.383(8) . ?