#------------------------------------------------------------------------------ #$Date: 2020-03-26 07:14:56 +0200 (Thu, 26 Mar 2020) $ #$Revision: 249729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240204.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_7240204 loop_ _publ_author_name 'Srinivasarao, Singireddi' 'Nandikolla, Adinarayana' 'Suresh, Amaroju' 'Calster, Kevin Van' 'De Voogt, Linda' 'Cappoen, Davie' 'Ghosh, Balaram' 'Aggarwal, Himanshu' 'Murugesan, Sankaranarayanan' 'Chandra Sekhar, Kondapalli Venkata Gowri' _publ_section_title ; Seeking potent anti-tubercular agents: design and synthesis of substituted-N-(6-(4-(pyrazine-2-carbonyl)piperazine/homopiperazine-1-yl)pyridin-3-yl)benzamide derivatives as anti-tubercular agents ; _journal_issue 21 _journal_name_full 'RSC Advances' _journal_page_first 12272 _journal_paper_doi 10.1039/D0RA01348J _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C19 H18 N8 O2' _chemical_formula_sum 'C19 H18 N8 O2' _chemical_formula_weight 390.41 _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 _atom_sites_solution_primary direct _audit_creation_date 2020-01-24 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-01-25 deposited with the CCDC. 2020-03-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.4675(15) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 30.7919(5) _cell_length_b 5.80932(8) _cell_length_c 9.90381(15) _cell_measurement_reflns_used 5983 _cell_measurement_temperature 100 _cell_measurement_theta_max 79.3370 _cell_measurement_theta_min 5.7990 _cell_volume 1760.32(5) _computing_cell_refinement 'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 100 _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -29.00 10.00 0.50 1.64 -- 0.00 77.00 150.00 78 2 \w -28.00 16.00 0.50 1.64 -- 0.00 -37.00 -90.00 88 3 \w -20.00 5.00 0.50 1.64 -- 0.00 -37.00-120.00 50 4 \w -69.00 18.00 0.50 1.64 -- 0.00 -37.00-180.00 174 5 \w -21.00 4.00 0.50 1.64 -- 0.00 77.00-120.00 50 6 \w 44.00 70.00 0.50 6.56 -- 107.20 -82.00 150.00 52 7 \w 35.00 140.00 0.50 6.56 -- 107.20 -82.00-180.00 210 8 \w 19.00 130.00 0.50 6.56 -- 107.20 -61.00-180.00 222 9 \w 81.00 120.00 0.50 6.56 -- 107.20 -82.00 90.00 78 10 \w 27.00 56.00 0.50 6.56 -- 107.20 -77.00-150.00 58 11 \w 95.00 170.00 0.50 6.56 -- 107.20 30.00 -30.00 150 12 \w 20.00 99.00 0.50 6.56 -- 107.20 -15.00-180.00 158 13 \w 158.00 197.00 0.50 6.56 -- 107.20 45.00 150.00 78 14 \w 86.00 111.00 0.50 6.56 -- 107.20 -82.00 150.00 50 15 \w 87.00 142.00 0.50 6.56 -- 107.20 45.00 150.00 110 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Pro: Kappa dual offset/far' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0480496000 _diffrn_orient_matrix_UB_12 -0.0259397000 _diffrn_orient_matrix_UB_13 -0.0606520000 _diffrn_orient_matrix_UB_21 -0.0141578000 _diffrn_orient_matrix_UB_22 -0.0056868000 _diffrn_orient_matrix_UB_23 0.1442598000 _diffrn_orient_matrix_UB_31 -0.0050434000 _diffrn_orient_matrix_UB_32 0.2639391000 _diffrn_orient_matrix_UB_33 -0.0028537000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_unetI/netI 0.0334 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.970 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 9609 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.970 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.603 _diffrn_reflns_theta_min 4.335 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.843 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.80136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'metallic yellowish yellow' _exptl_crystal_colour_lustre metallic _exptl_crystal_colour_modifier yellowish _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.473 _exptl_crystal_description block _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.715 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 316 _refine_ls_number_reflns 3735 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0430 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+1.0885P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1147 _refine_ls_wR_factor_ref 0.1173 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3424 _reflns_number_total 3735 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra01348j2.cif _cod_data_source_block KVGCS_P2 _cod_database_code 7240204 _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_estimated_absorpt_t_max 0.959 _shelx_estimated_absorpt_t_min 0.849 _reflns_odcompleteness_completeness 99.53 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 71.98 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2. Others Fixed Sof: O2A(0.66) C15A(0.66) C19A(0.6) H19A(0.6) N8A(0.6) N7A(0.6) C17A(0.6) H17A(0.6) N7B(0.4) N8B(0.4) C17B(0.4) H17B(0.4) C19B(0.4) H19B(0.4) C15B(0.34) O2B(0.34) 3.a Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B), C14(H14A,H14B) 3.b Aromatic/amide H refined with riding coordinates: N3(H3), C7(H7), C2(H2), C8(H8), C3(H3A), C10(H10), C1(H1), C18(H18), C19A(H19A), C17A(H17A), C17B(H17B), C19B(H19B) ; _shelx_res_file ; TITL exp_544_P_2 in P21/c #14 exp_544_p_2.res created by SHELXL-2018/3 at 20:09:55 on 24-Jan-2020 REM reset to P21/c #14 CELL 1.54184 30.791938 5.809317 9.903814 90 96.4675 90 ZERR 4 0.000482 0.00008 0.000153 0 0.0015 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 76 72 32 8 L.S. 4 0 0 PLAN 20 SIZE 0.05 0.1 0.2 TEMP -173.15 BOND fmap 2 53 acta REM REM REM WGHT 0.052100 1.088500 FVAR 3.11232 N5 3 0.263975 0.509135 0.980235 11.00000 0.01974 0.01425 = 0.01915 0.00296 0.00689 0.00149 O1 4 0.124237 0.092205 1.338625 11.00000 0.02555 0.01651 = 0.02797 -0.00320 0.01131 -0.00071 N4 3 0.226989 0.320491 1.138088 11.00000 0.02216 0.01637 = 0.02582 0.00347 0.01035 0.00186 C9 1 0.231175 0.512152 1.064578 11.00000 0.01810 0.01509 = 0.01607 -0.00094 0.00305 -0.00057 N1 3 0.037148 0.164645 1.624759 11.00000 0.02445 0.01700 = 0.02392 0.00093 0.00936 -0.00061 C5 1 0.116782 0.289043 1.375073 11.00000 0.01708 0.01688 = 0.01899 -0.00025 0.00382 -0.00011 N3 3 0.135117 0.481764 1.330457 11.00000 0.01898 0.01532 = 0.02197 -0.00090 0.00820 0.00002 AFIX 43 H3 2 0.126638 0.614058 1.361944 11.00000 -1.20000 AFIX 0 C6 1 0.166882 0.489535 1.237169 11.00000 0.01729 0.01707 = 0.01775 -0.00120 0.00462 -0.00128 N2 3 0.076312 0.546654 1.512610 11.00000 0.02108 0.01532 = 0.02301 0.00033 0.00744 0.00017 C7 1 0.171132 0.689138 1.161279 11.00000 0.01845 0.01585 = 0.02110 -0.00060 0.00398 0.00190 AFIX 43 H7 2 0.151978 0.815455 1.169061 11.00000 -1.20000 AFIX 0 C2 1 0.029170 0.380522 1.661258 11.00000 0.02112 0.01949 = 0.02202 0.00084 0.00832 0.00113 AFIX 43 H2 2 0.009595 0.405905 1.727358 11.00000 -1.20000 AFIX 0 C11 1 0.275194 0.715107 0.906284 11.00000 0.02314 0.01404 = 0.01908 0.00221 0.00699 0.00195 AFIX 23 H11A 2 0.296388 0.809773 0.964912 11.00000 -1.20000 H11B 2 0.248616 0.808653 0.881486 11.00000 -1.20000 AFIX 0 C8 1 0.203214 0.702502 1.074954 11.00000 0.01980 0.01474 = 0.01879 0.00167 0.00372 0.00074 AFIX 43 H8 2 0.206453 0.837866 1.023206 11.00000 -1.20000 AFIX 0 C4 1 0.084838 0.330273 1.476914 11.00000 0.01739 0.01584 = 0.01850 -0.00059 0.00359 0.00075 N6 3 0.332550 0.493178 0.811334 11.00000 0.02279 0.01930 = 0.02065 0.00464 0.00831 0.00342 C3 1 0.048485 0.569106 1.605969 11.00000 0.02388 0.01673 = 0.02534 -0.00119 0.00960 0.00179 AFIX 43 H3A 2 0.041688 0.719107 1.635504 11.00000 -1.20000 AFIX 0 C10 1 0.195905 0.311031 1.222245 11.00000 0.02199 0.01724 = 0.02522 0.00429 0.00888 0.00092 AFIX 43 H10 2 0.193608 0.175201 1.274382 11.00000 -1.20000 AFIX 0 C1 1 0.065314 0.141987 1.531658 11.00000 0.02362 0.01605 = 0.02378 -0.00070 0.00856 0.00026 AFIX 43 H1 2 0.072123 -0.008054 1.502216 11.00000 -1.20000 AFIX 0 C13 1 0.322012 0.287756 0.888195 11.00000 0.02742 0.01889 = 0.02486 0.00298 0.00937 0.00223 AFIX 23 H13A 2 0.348967 0.197931 0.914427 11.00000 -1.20000 H13B 2 0.301341 0.188951 0.830408 11.00000 -1.20000 AFIX 0 C12 1 0.294948 0.645134 0.778574 11.00000 0.02217 0.01780 = 0.01744 0.00290 0.00564 0.00324 AFIX 23 H12A 2 0.272587 0.565096 0.715824 11.00000 -1.20000 H12B 2 0.304273 0.784511 0.732056 11.00000 -1.20000 AFIX 0 C14 1 0.301906 0.357596 1.013666 11.00000 0.02516 0.01877 = 0.02481 0.00558 0.00965 0.00585 AFIX 23 H14A 2 0.292624 0.218158 1.060219 11.00000 -1.20000 H14B 2 0.324046 0.438462 1.076775 11.00000 -1.20000 AFIX 0 C16 1 0.405636 0.356706 0.782078 11.00000 0.02361 0.03475 = 0.04029 0.01692 0.01536 0.00462 PART 3 O2A 4 0.366387 0.631911 0.635655 10.66000 0.03268 0.03997 = 0.03177 0.01715 0.01758 0.00868 C15A 1 0.365954 0.502767 0.732842 10.66000 0.02317 0.02193 = 0.01953 -0.00049 0.00507 0.00013 PART 0 C18 1 0.473485 0.082613 0.842070 11.00000 0.03238 0.05256 = 0.03229 0.01036 0.00750 0.01818 PART 2 AFIX 43 H18 2 0.495752 -0.027888 0.866235 11.00000 -1.20000 AFIX 0 PART 0 PART 1 C19A 1 0.443959 0.419135 0.877517 10.60000 0.04186 0.05032 = 0.03088 0.00218 0.00007 0.01794 AFIX 43 H19A 2 0.444894 0.565146 0.920943 10.60000 -1.20000 AFIX 0 N8A 3 0.477330 0.274305 0.903961 10.60000 0.04332 0.06079 = 0.03683 0.00211 -0.00560 0.02219 N7A 3 0.402524 0.160750 0.728345 10.60000 0.02509 0.03947 = 0.06882 0.01753 0.00036 0.00129 C17A 1 0.436161 0.015412 0.752699 10.60000 0.03049 0.03846 = 0.04585 0.01139 0.00543 0.00502 AFIX 43 H17A 2 0.435166 -0.131759 0.710644 10.60000 -1.20000 AFIX 0 PART 0 PART 2 N7B 3 0.416942 0.212782 0.677974 10.40000 0.02981 0.03682 = 0.02412 -0.00366 0.00517 0.01090 N8B 3 0.462671 0.242448 0.935944 10.40000 0.03446 0.04173 = 0.03461 0.00175 -0.00872 0.00893 C17B 1 0.452320 0.085437 0.717424 10.40000 0.04069 0.04067 = 0.03564 0.00280 0.01120 0.02030 AFIX 43 H17B 2 0.463166 -0.010512 0.651145 10.40000 -1.20000 AFIX 0 C19B 1 0.426994 0.369869 0.897639 10.40000 0.03539 0.03629 = 0.03576 -0.00886 -0.00347 0.01285 AFIX 43 H19B 2 0.417411 0.475477 0.961270 10.40000 -1.20000 AFIX 0 PART 0 PART 4 C15B 1 0.371834 0.551356 0.778267 10.34000 0.01984 0.02840 = 0.03492 0.01234 0.00510 -0.00367 O2B 4 0.379222 0.737196 0.726152 10.34000 0.02583 0.05403 = 0.13266 0.06554 0.02074 0.00362 HKLF 4 REM exp_544_P_2 in P21/c #14 REM wR2 = 0.1173, GooF = S = 1.028, Restrained GooF = 1.028 for all data REM R1 = 0.0430 for 3424 Fo > 4sig(Fo) and 0.0461 for all 3735 data REM 316 parameters refined using 0 restraints END WGHT 0.0521 1.0884 REM Highest difference peak 0.715, deepest hole -0.300, 1-sigma level 0.048 Q1 1 0.3395 0.3995 0.9602 11.00000 0.05 0.72 Q2 1 0.2865 0.3197 0.9431 11.00000 0.05 0.23 Q3 1 0.0976 0.3156 1.4269 11.00000 0.05 0.22 Q4 1 0.1808 0.6762 1.1073 11.00000 0.05 0.20 Q5 1 0.4047 0.5913 0.4958 11.00000 0.05 0.19 Q6 1 0.3593 0.2419 0.9516 11.00000 0.05 0.18 Q7 1 0.4193 0.4166 0.8245 11.00000 0.05 0.17 Q8 1 0.2805 0.6730 0.8399 11.00000 0.05 0.16 Q9 1 0.1581 0.1012 1.3226 11.00000 0.05 0.14 Q10 1 0.1003 -0.0405 1.3923 11.00000 0.05 0.14 Q11 1 0.2178 0.5816 1.0406 11.00000 0.05 0.14 Q12 1 0.3207 0.7724 0.8708 11.00000 0.05 0.14 Q13 1 0.0419 0.4806 1.6374 11.00000 0.05 0.13 Q14 1 0.2412 0.7510 0.8422 11.00000 0.05 0.13 Q15 1 0.2758 0.2179 0.8768 11.00000 0.05 0.13 Q16 1 0.0396 0.0299 1.7149 11.00000 0.05 0.13 Q17 1 0.2202 0.6588 1.0991 11.00000 0.05 0.13 Q18 1 0.1207 0.0245 1.4520 11.00000 0.05 0.13 Q19 1 0.0775 0.2359 1.5019 11.00000 0.05 0.12 Q20 1 0.2638 0.2590 1.1075 11.00000 0.05 0.12 ; _shelx_res_checksum 66833 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.519 _oxdiff_exptl_absorpt_empirical_full_min 0.627 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 N5 N 0.26398(4) 0.50914(18) 0.98023(11) 0.0174(2) Uani 1 1 d . . . . . O1 O 0.12424(3) 0.09220(16) 1.33863(10) 0.0227(2) Uani 1 1 d . . . . . N4 N 0.22699(4) 0.32049(19) 1.13809(12) 0.0209(2) Uani 1 1 d . . . . . C9 C 0.23118(4) 0.5122(2) 1.06458(12) 0.0163(3) Uani 1 1 d . . . . . N1 N 0.03715(4) 0.16464(19) 1.62476(12) 0.0213(2) Uani 1 1 d . . . . . C5 C 0.11678(4) 0.2890(2) 1.37507(13) 0.0175(3) Uani 1 1 d . . . . . N3 N 0.13512(3) 0.48176(19) 1.33046(11) 0.0183(2) Uani 1 1 d . . . . . H3 H 0.126638 0.614058 1.361944 0.022 Uiso 1 1 calc R . . . . C6 C 0.16688(4) 0.4895(2) 1.23717(13) 0.0172(3) Uani 1 1 d . . . . . N2 N 0.07631(4) 0.54665(19) 1.51261(12) 0.0194(2) Uani 1 1 d . . . . . C7 C 0.17113(4) 0.6891(2) 1.16128(13) 0.0183(3) Uani 1 1 d . . . . . H7 H 0.151978 0.815455 1.169061 0.022 Uiso 1 1 calc R . . . . C2 C 0.02917(4) 0.3805(2) 1.66126(14) 0.0204(3) Uani 1 1 d . . . . . H2 H 0.009595 0.405905 1.727358 0.025 Uiso 1 1 calc R . . . . C11 C 0.27519(4) 0.7151(2) 0.90628(13) 0.0184(3) Uani 1 1 d . . . . . H11A H 0.296388 0.809773 0.964912 0.022 Uiso 1 1 calc R . . . . H11B H 0.248616 0.808653 0.881486 0.022 Uiso 1 1 calc R . . . . C8 C 0.20321(4) 0.7025(2) 1.07495(13) 0.0177(3) Uani 1 1 d . . . . . H8 H 0.206453 0.837866 1.023206 0.021 Uiso 1 1 calc R . . . . C4 C 0.08484(4) 0.3303(2) 1.47691(13) 0.0171(3) Uani 1 1 d . . . . . N6 N 0.33255(4) 0.49318(19) 0.81133(12) 0.0205(2) Uani 1 1 d . . . . . C3 C 0.04848(4) 0.5691(2) 1.60597(14) 0.0215(3) Uani 1 1 d . . . . . H3A H 0.041688 0.719107 1.635504 0.026 Uiso 1 1 calc R . . . . C10 C 0.19591(4) 0.3110(2) 1.22224(14) 0.0210(3) Uani 1 1 d . . . . . H10 H 0.193608 0.175201 1.274382 0.025 Uiso 1 1 calc R . . . . C1 C 0.06531(4) 0.1420(2) 1.53166(14) 0.0207(3) Uani 1 1 d . . . . . H1 H 0.072123 -0.008054 1.502216 0.025 Uiso 1 1 calc R . . . . C13 C 0.32201(5) 0.2878(2) 0.88819(14) 0.0232(3) Uani 1 1 d . . . . . H13A H 0.348967 0.197931 0.914427 0.028 Uiso 1 1 calc R . . . . H13B H 0.301341 0.188951 0.830408 0.028 Uiso 1 1 calc R . . . . C12 C 0.29495(4) 0.6451(2) 0.77857(13) 0.0189(3) Uani 1 1 d . . . . . H12A H 0.272587 0.565096 0.715824 0.023 Uiso 1 1 calc R . . . . H12B H 0.304273 0.784511 0.732056 0.023 Uiso 1 1 calc R . . . . C14 C 0.30191(5) 0.3576(2) 1.01367(14) 0.0224(3) Uani 1 1 d . . . . . H14A H 0.292624 0.218158 1.060219 0.027 Uiso 1 1 calc R . . . . H14B H 0.324046 0.438462 1.076775 0.027 Uiso 1 1 calc R . . . . C16 C 0.40564(5) 0.3567(3) 0.78208(17) 0.0320(4) Uani 1 1 d . . . . . O2A O 0.36639(6) 0.6319(3) 0.63565(19) 0.0337(4) Uani 0.66 1 d . . P A 3 C15A C 0.36595(13) 0.5028(7) 0.7328(3) 0.0213(7) Uani 0.66 1 d . . P A 3 C18 C 0.47349(6) 0.0826(3) 0.84207(17) 0.0388(4) Uani 1 1 d . . . . . H18 H 0.495752 -0.027888 0.866235 0.047 Uiso 1 1 calc R . . B 2 C19A C 0.44396(14) 0.4191(9) 0.8775(4) 0.0413(10) Uani 0.6 1 d . . P A 1 H19A H 0.444894 0.565146 0.920943 0.050 Uiso 0.6 1 calc R . P A 1 N8A N 0.47733(14) 0.2743(10) 0.9040(5) 0.0478(11) Uani 0.6 1 d . . P A 1 N7A N 0.40252(9) 0.1607(5) 0.7283(4) 0.0448(7) Uani 0.6 1 d . . P A 1 C17A C 0.43616(11) 0.0154(6) 0.7527(4) 0.0382(7) Uani 0.6 1 d . . P A 1 H17A H 0.435166 -0.131759 0.710644 0.046 Uiso 0.6 1 calc R . P A 1 N7B N 0.41694(13) 0.2128(7) 0.6780(4) 0.0301(8) Uani 0.4 1 d . . P A 2 N8B N 0.46267(19) 0.2424(12) 0.9359(6) 0.0379(12) Uani 0.4 1 d . . P A 2 C17B C 0.45232(18) 0.0854(9) 0.7174(5) 0.0385(10) Uani 0.4 1 d . . P A 2 H17B H 0.463166 -0.010512 0.651145 0.046 Uiso 0.4 1 calc R . P A 2 C19B C 0.4270(2) 0.3699(11) 0.8976(7) 0.0364(13) Uani 0.4 1 d . . P A 2 H19B H 0.417411 0.475477 0.961270 0.044 Uiso 0.4 1 calc R . P A 2 C15B C 0.3718(2) 0.5514(14) 0.7783(7) 0.0276(15) Uani 0.34 1 d . . P A 4 O2B O 0.37922(13) 0.7372(9) 0.7262(7) 0.0699(18) Uani 0.34 1 d . . P A 4 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 0.0197(5) 0.0142(5) 0.0191(5) 0.0030(4) 0.0069(4) 0.0015(4) O1 0.0256(5) 0.0165(5) 0.0280(5) -0.0032(4) 0.0113(4) -0.0007(4) N4 0.0222(6) 0.0164(5) 0.0258(6) 0.0035(4) 0.0104(5) 0.0019(4) C9 0.0181(6) 0.0151(6) 0.0161(6) -0.0009(5) 0.0031(5) -0.0006(5) N1 0.0244(6) 0.0170(5) 0.0239(6) 0.0009(4) 0.0094(5) -0.0006(4) C5 0.0171(6) 0.0169(6) 0.0190(6) -0.0002(5) 0.0038(5) -0.0001(5) N3 0.0190(5) 0.0153(5) 0.0220(5) -0.0009(4) 0.0082(4) 0.0000(4) C6 0.0173(6) 0.0171(6) 0.0177(6) -0.0012(5) 0.0046(5) -0.0013(5) N2 0.0211(5) 0.0153(5) 0.0230(5) 0.0003(4) 0.0074(4) 0.0002(4) C7 0.0184(6) 0.0158(6) 0.0211(6) -0.0006(5) 0.0040(5) 0.0019(5) C2 0.0211(6) 0.0195(6) 0.0220(6) 0.0008(5) 0.0083(5) 0.0011(5) C11 0.0231(6) 0.0140(6) 0.0191(6) 0.0022(5) 0.0070(5) 0.0020(5) C8 0.0198(6) 0.0147(6) 0.0188(6) 0.0017(5) 0.0037(5) 0.0007(5) C4 0.0174(6) 0.0158(6) 0.0185(6) -0.0006(5) 0.0036(5) 0.0007(5) N6 0.0228(6) 0.0193(6) 0.0206(5) 0.0046(4) 0.0083(4) 0.0034(4) C3 0.0239(6) 0.0167(6) 0.0253(7) -0.0012(5) 0.0096(5) 0.0018(5) C10 0.0220(6) 0.0172(6) 0.0252(6) 0.0043(5) 0.0089(5) 0.0009(5) C1 0.0236(6) 0.0161(6) 0.0238(6) -0.0007(5) 0.0086(5) 0.0003(5) C13 0.0274(7) 0.0189(6) 0.0249(7) 0.0030(5) 0.0094(5) 0.0022(5) C12 0.0222(6) 0.0178(6) 0.0174(6) 0.0029(5) 0.0056(5) 0.0032(5) C14 0.0252(7) 0.0188(6) 0.0248(7) 0.0056(5) 0.0096(5) 0.0058(5) C16 0.0236(7) 0.0348(9) 0.0403(9) 0.0169(7) 0.0154(6) 0.0046(6) O2A 0.0327(9) 0.0400(10) 0.0318(9) 0.0171(8) 0.0176(7) 0.0087(8) C15A 0.0232(15) 0.0219(16) 0.0195(16) -0.0005(11) 0.0051(13) 0.0001(11) C18 0.0324(8) 0.0526(11) 0.0323(8) 0.0104(8) 0.0075(7) 0.0182(8) C19A 0.042(2) 0.050(2) 0.0309(17) 0.0022(16) 0.0001(17) 0.018(2) N8A 0.043(3) 0.061(3) 0.037(2) 0.0021(17) -0.0056(16) 0.022(2) N7A 0.0251(13) 0.0395(16) 0.069(2) 0.0175(14) 0.0004(13) 0.0013(11) C17A 0.0305(16) 0.0385(17) 0.0458(19) 0.0114(14) 0.0054(13) 0.0050(13) N7B 0.0298(19) 0.037(2) 0.0241(17) -0.0037(15) 0.0052(14) 0.0109(16) N8B 0.034(3) 0.042(3) 0.035(3) 0.002(2) -0.009(2) 0.009(2) C17B 0.041(3) 0.041(3) 0.036(2) 0.003(2) 0.011(2) 0.020(2) C19B 0.035(3) 0.036(3) 0.036(3) -0.009(2) -0.003(2) 0.013(2) C15B 0.020(3) 0.028(4) 0.035(4) 0.012(3) 0.005(3) -0.004(2) O2B 0.0258(19) 0.054(3) 0.133(5) 0.066(3) 0.021(3) 0.0036(19) 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 C9 N5 C11 121.45(10) . . ? C9 N5 C14 119.20(10) . . ? C11 N5 C14 112.07(10) . . ? C10 N4 C9 119.33(11) . . ? N5 C9 C8 123.17(11) . . ? N4 C9 N5 115.99(11) . . ? N4 C9 C8 120.84(11) . . ? C2 N1 C1 115.53(11) . . ? O1 C5 N3 125.22(12) . . ? O1 C5 C4 120.19(11) . . ? N3 C5 C4 114.59(11) . . ? C5 N3 C6 125.68(11) . . ? C7 C6 N3 119.34(11) . . ? C10 C6 N3 123.00(12) . . ? C10 C6 C7 117.57(12) . . ? C3 N2 C4 115.74(11) . . ? C8 C7 C6 119.84(12) . . ? N1 C2 C3 122.29(12) . . ? N5 C11 C12 109.69(10) . . ? C7 C8 C9 119.08(12) . . ? N2 C4 C5 119.23(11) . . ? N2 C4 C1 122.01(12) . . ? C1 C4 C5 118.75(11) . . ? C12 N6 C13 112.89(11) . . ? C15A N6 C13 123.69(19) . . ? C15A N6 C12 118.66(19) . . ? C15B N6 C13 126.3(4) . . ? C15B N6 C12 120.7(4) . . ? N2 C3 C2 122.18(12) . . ? N4 C10 C6 123.34(12) . . ? N1 C1 C4 122.23(12) . . ? N6 C13 C14 110.10(11) . . ? N6 C12 C11 110.97(10) . . ? N5 C14 C13 111.45(11) . . ? N7A C16 C19A 120.9(3) . . ? C19B C16 N7B 124.0(3) . . ? N6 C15A C16 115.2(3) . . ? O2A C15A N6 123.5(3) . . ? O2A C15A C16 121.0(3) . . ? N8A C18 C17A 124.4(3) . . ? C17B C18 N8B 119.1(4) . . ? N8A C19A C16 121.1(4) . . ? C18 N8A C19A 115.5(4) . . ? C16 N7A C17A 118.4(3) . . ? N7A C17A C18 119.6(3) . . ? C17B N7B C16 112.1(3) . . ? C19B N8B C18 115.6(5) . . ? C18 C17B N7B 125.1(4) . . ? C16 C19B N8B 123.4(6) . . ? N6 C15B C16 116.1(5) . . ? O2B C15B N6 122.8(7) . . ? O2B C15B C16 120.0(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 N5 C9 1.3814(16) . ? N5 C11 1.4644(16) . ? N5 C14 1.4703(16) . ? O1 C5 1.2285(16) . ? N4 C9 1.3444(16) . ? N4 C10 1.3392(17) . ? C9 C8 1.4123(17) . ? N1 C2 1.3356(17) . ? N1 C1 1.3416(17) . ? C5 N3 1.3504(16) . ? C5 C4 1.5052(17) . ? N3 C6 1.4198(16) . ? C6 C7 1.3960(18) . ? C6 C10 1.3877(18) . ? N2 C4 1.3398(16) . ? N2 C3 1.3359(17) . ? C7 C8 1.3795(18) . ? C2 C3 1.3882(19) . ? C11 C12 1.5193(17) . ? C4 C1 1.3875(18) . ? N6 C13 1.4712(17) . ? N6 C12 1.4630(16) . ? N6 C15A 1.358(4) . ? N6 C15B 1.332(8) . ? C13 C14 1.5051(18) . ? C16 C15A 1.522(4) . ? C16 C19A 1.472(5) . ? C16 N7A 1.256(4) . ? C16 N7B 1.401(4) . ? C16 C19B 1.256(7) . ? C16 C15B 1.534(8) . ? O2A C15A 1.222(4) . ? C18 N8A 1.270(6) . ? C18 C17A 1.424(4) . ? C18 N8B 1.381(7) . ? C18 C17B 1.330(5) . ? C19A N8A 1.331(7) . ? N7A C17A 1.337(4) . ? N7B C17B 1.338(6) . ? N8B C19B 1.343(9) . ? C15B O2B 1.229(9) . ?