#------------------------------------------------------------------------------ #$Date: 2020-10-06 12:14:50 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257582 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240445.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_7240445 loop_ _publ_author_name 'Hadian, Mojgan' 'Shaabani, Shabnam' 'Patil, Pravin' 'Shishkina, Svitlana V.' 'B\"oltz, Harry' 'D\"omling, Alexander' _publ_section_title ; Sustainability by design: automated nanoscale 2,3,4-trisubstituted quinazoline diversity ; _journal_issue 8 _journal_name_full 'Green Chemistry' _journal_page_first 2459 _journal_page_last 2467 _journal_paper_doi 10.1039/D0GC00363H _journal_volume 22 _journal_year 2020 _chemical_formula_sum 'C19 H23 N3 O3' _chemical_formula_weight 341.40 _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-2016/6 _audit_update_record ; 2019-12-17 deposited with the CCDC. 2020-02-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.31(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.864(3) _cell_length_b 11.162(3) _cell_length_c 13.889(5) _cell_measurement_reflns_used 453 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.079 _cell_measurement_theta_min 3.471 _cell_volume 1815.0(9) _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.1827 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1767 _diffrn_reflns_av_unetI/netI 0.1703 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 12145 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 2.972 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.36107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.249 _exptl_crystal_description plate _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.130 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.157 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.884 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 3136 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.884 _refine_ls_R_factor_all 0.2181 _refine_ls_R_factor_gt 0.0746 _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^)+(0.0342P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1287 _refine_ls_wR_factor_ref 0.1705 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1164 _reflns_number_total 3136 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0gc00363h2.cif _cod_data_source_block ad37 _cod_depositor_comments 'Adding full bibliography for 7240443--7240446.cif.' _cod_original_cell_volume 1815.1(10) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240445 _shelx_shelxl_version_number 2016/6 _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 0.989 _shelx_estimated_absorpt_t_max 0.996 _shelx_res_file ; TITL ad37_a.res in P2(1)/c ad37.res created by SHELXL-2016/6 at 11:16:58 on 17-Dec-2019 CELL 0.71073 11.8636 11.162 13.8895 90 99.307 90 ZERR 4 0.0034 0.0034 0.005 0 0.031 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 76 92 12 12 L.S. 4 0 0 PLAN 20 BOND $H list 4 fmap 2 53 acta OMIT 0 50 conf size 0.13 0.12 0.05 temp 20 eqiv $1 1-x,2-y,1-z htab n1 o2_$1 eqiv $2 1-x,-0.5+y,0.5-z htab n3 o2_$2 OMIT -5 3 2 OMIT 4 6 10 OMIT 6 8 5 OMIT -5 10 8 OMIT -9 8 9 OMIT 7 1 9 OMIT -10 8 4 OMIT -3 6 7 OMIT 10 1 0 OMIT -8 4 2 OMIT 2 11 2 OMIT 8 4 8 OMIT -1 0 16 OMIT 13 3 1 OMIT -12 6 4 OMIT 8 0 6 OMIT 7 10 5 OMIT 0 4 14 OMIT -11 7 7 OMIT 9 6 2 OMIT -10 5 8 OMIT 2 10 0 OMIT -7 4 1 OMIT 5 11 2 OMIT 7 3 4 OMIT -7 4 13 OMIT 3 9 0 OMIT -10 6 5 OMIT -6 4 14 OMIT -6 7 1 OMIT 8 7 0 OMIT -7 10 2 OMIT -9 7 2 OMIT 3 4 5 OMIT 12 5 1 OMIT -9 2 7 OMIT 4 5 1 OMIT -7 7 10 OMIT -6 8 4 OMIT 11 1 4 OMIT -12 1 5 OMIT 0 10 2 OMIT -1 5 3 OMIT 0 13 1 OMIT 2 8 8 OMIT 6 5 12 OMIT 6 10 4 OMIT -3 11 8 OMIT -9 6 3 OMIT 3 9 8 OMIT -4 8 6 WGHT 0.034200 FVAR 0.67243 O1 4 0.595298 0.892362 0.601313 11.00000 0.10002 0.09246 = 0.03943 -0.00805 0.01716 -0.00968 O2 4 0.702373 0.992995 0.512996 11.00000 0.06471 0.06052 = 0.08123 0.00220 -0.00259 -0.01178 O3 4 0.177887 0.612472 0.295106 11.00000 0.11469 0.11157 = 0.05911 -0.02333 0.04147 -0.04471 N1 3 0.325251 0.860336 0.312417 11.00000 0.05285 0.06268 = 0.04425 -0.01238 0.00319 0.00839 AFIX 43 H1N 2 0.313309 0.913100 0.354750 11.00000 -1.20000 AFIX 0 N2 3 0.402006 0.679826 0.281242 11.00000 0.06004 0.05230 = 0.03916 -0.00867 0.00269 0.00564 N3 3 0.182126 0.495370 0.162783 11.00000 0.05781 0.05186 = 0.07700 -0.01330 0.01686 -0.00977 AFIX 43 H3N 2 0.216336 0.485659 0.113275 11.00000 -1.20000 AFIX 0 C1 1 0.314490 0.660300 0.193557 11.00000 0.05937 0.05460 = 0.03935 -0.01133 0.00554 -0.00668 AFIX 13 H1 2 0.348755 0.617653 0.143797 11.00000 -1.20000 AFIX 0 C2 1 0.267916 0.779004 0.153441 11.00000 0.05408 0.05323 = 0.04020 -0.00898 0.00529 -0.00317 C3 1 0.220420 0.791113 0.055969 11.00000 0.06089 0.07286 = 0.04802 -0.00614 0.01255 -0.00404 AFIX 43 H3 2 0.219256 0.726571 0.013476 11.00000 -1.20000 AFIX 0 C4 1 0.175188 0.899413 0.022996 11.00000 0.09362 0.08980 = 0.05125 0.00985 -0.00092 0.01775 AFIX 43 H4 2 0.143566 0.908350 -0.042374 11.00000 -1.20000 AFIX 0 C5 1 0.176106 0.994789 0.085504 11.00000 0.08951 0.07098 = 0.06872 0.01017 0.00047 0.01210 AFIX 43 H5 2 0.144496 1.067567 0.062358 11.00000 -1.20000 AFIX 0 C6 1 0.223806 0.983234 0.182766 11.00000 0.06033 0.06680 = 0.07324 -0.01092 0.00723 0.00647 AFIX 43 H6 2 0.225044 1.047587 0.225452 11.00000 -1.20000 AFIX 0 C7 1 0.269595 0.873649 0.214947 11.00000 0.04622 0.05804 = 0.04825 -0.00665 0.00205 0.00062 C8 1 0.394774 0.770247 0.341082 11.00000 0.04442 0.06288 = 0.04584 -0.00283 0.01029 -0.00129 C9 1 0.467249 0.780848 0.438808 11.00000 0.05845 0.06454 = 0.03682 -0.00410 0.00055 -0.00335 AFIX 23 H9A 2 0.482534 0.701409 0.466132 11.00000 -1.20000 H9B 2 0.425821 0.825238 0.481924 11.00000 -1.20000 AFIX 0 C10 1 0.580575 0.843949 0.434148 11.00000 0.06519 0.08968 = 0.04745 -0.00061 0.01181 -0.01325 AFIX 23 H10A 2 0.635930 0.784159 0.422007 11.00000 -1.20000 H10B 2 0.569631 0.898214 0.378874 11.00000 -1.20000 AFIX 0 C11 1 0.630509 0.914332 0.524410 11.00000 0.04783 0.05661 = 0.05451 -0.00533 -0.00140 0.00521 C12 1 0.494140 0.590721 0.301546 11.00000 0.06222 0.06972 = 0.05269 -0.01238 0.00001 0.00533 AFIX 23 H12A 2 0.531712 0.583561 0.244759 11.00000 -1.20000 H12B 2 0.550291 0.618925 0.355384 11.00000 -1.20000 AFIX 0 C13 1 0.453844 0.472924 0.325800 11.00000 0.07719 0.05410 = 0.05758 -0.00605 0.00632 0.00162 C14 1 0.430159 0.376914 0.342670 11.00000 0.09505 0.07031 = 0.06268 0.00810 -0.00523 0.00304 AFIX 163 H14 2 0.410866 0.298710 0.356410 11.00000 -1.20000 AFIX 0 C15 1 0.216605 0.585147 0.222337 11.00000 0.06971 0.05968 = 0.04583 0.00361 -0.00246 -0.00769 C16 1 0.089406 0.409930 0.174109 11.00000 0.07077 0.06219 = 0.10277 -0.01618 0.00609 -0.01998 C17 1 0.115161 0.347542 0.271862 11.00000 0.21341 0.16075 = 0.16192 0.08502 -0.03800 -0.12562 AFIX 137 H17A 2 0.186715 0.306007 0.276713 11.00000 -1.50000 H17B 2 0.055511 0.291206 0.277746 11.00000 -1.50000 H17C 2 0.119604 0.405815 0.323172 11.00000 -1.50000 AFIX 0 C18 1 0.085051 0.320626 0.092346 11.00000 0.12492 0.11760 = 0.25797 -0.10213 0.08343 -0.06406 AFIX 137 H18A 2 0.071444 0.361865 0.030908 11.00000 -1.50000 H18B 2 0.024460 0.264456 0.095430 11.00000 -1.50000 H18C 2 0.156473 0.278617 0.098570 11.00000 -1.50000 AFIX 0 C19 1 -0.023344 0.474343 0.161354 11.00000 0.07009 0.12678 = 0.17484 -0.02031 0.03376 -0.02163 AFIX 137 H19A 2 -0.018834 0.539968 0.206490 11.00000 -1.50000 H19B 2 -0.082049 0.419874 0.173558 11.00000 -1.50000 H19C 2 -0.041136 0.504310 0.095870 11.00000 -1.50000 AFIX 0 HKLF 4 REM ad37_a.res in P2(1)/c REM R1 = 0.0746 for 1164 Fo > 4sig(Fo) and 0.2181 for all 3136 data REM 229 parameters refined using 0 restraints END WGHT 0.0342 0.0000 REM Highest difference peak 0.157, deepest hole -0.189, 1-sigma level 0.045 Q1 1 0.7809 0.9921 0.6105 11.00000 0.05 0.16 Q2 1 0.0187 0.5129 0.2676 11.00000 0.05 0.15 Q3 1 0.4805 0.6301 0.4931 11.00000 0.05 0.15 Q4 1 0.1813 0.2420 0.1658 11.00000 0.05 0.15 Q5 1 0.5326 0.4803 0.4454 11.00000 0.05 0.15 Q6 1 0.0921 0.5576 0.1405 11.00000 0.05 0.15 Q7 1 0.0255 0.5041 0.0525 11.00000 0.05 0.15 Q8 1 0.5690 0.6229 0.4622 11.00000 0.05 0.15 Q9 1 0.1159 0.5417 0.0570 11.00000 0.05 0.15 Q10 1 0.2827 1.0310 -0.0717 11.00000 0.05 0.14 Q11 1 0.1998 0.6237 0.0195 11.00000 0.05 0.14 Q12 1 0.1561 0.3135 0.1608 11.00000 0.05 0.14 Q13 1 0.6541 0.9967 0.4376 11.00000 0.05 0.14 Q14 1 0.0868 0.3043 0.3058 11.00000 0.05 0.14 Q15 1 0.0620 0.2265 0.1498 11.00000 0.05 0.14 Q16 1 0.6044 0.8475 0.3817 11.00000 0.05 0.14 Q17 1 0.7322 0.8219 0.5421 11.00000 0.05 0.14 Q18 1 0.3729 0.9246 0.4828 11.00000 0.05 0.13 Q19 1 0.1617 0.9961 0.2844 11.00000 0.05 0.13 Q20 1 0.6845 0.8985 0.6865 11.00000 0.05 0.13 ; _shelx_res_checksum 27644 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 O1 O 0.5953(3) 0.8924(3) 0.6013(2) 0.0767(11) Uani 1 1 d . . . . . O2 O 0.7024(3) 0.9930(3) 0.5130(2) 0.0704(10) Uani 1 1 d . . . . . O3 O 0.1779(3) 0.6125(3) 0.2951(3) 0.0921(14) Uani 1 1 d . . . . . N1 N 0.3253(3) 0.8603(3) 0.3124(3) 0.0538(10) Uani 1 1 d . . . . . H1N H 0.313309 0.913100 0.354750 0.065 Uiso 1 1 calc R U . . . N2 N 0.4020(3) 0.6798(3) 0.2812(3) 0.0511(10) Uani 1 1 d . . . . . N3 N 0.1821(3) 0.4954(3) 0.1628(3) 0.0616(11) Uani 1 1 d . . . . . H3N H 0.216336 0.485659 0.113275 0.074 Uiso 1 1 calc R U . . . C1 C 0.3145(4) 0.6603(4) 0.1936(3) 0.0514(12) Uani 1 1 d . . . . . H1 H 0.348755 0.617653 0.143797 0.062 Uiso 1 1 calc R U . . . C2 C 0.2679(4) 0.7790(4) 0.1534(3) 0.0494(12) Uani 1 1 d . . . . . C3 C 0.2204(4) 0.7911(5) 0.0560(3) 0.0602(14) Uani 1 1 d . . . . . H3 H 0.219256 0.726571 0.013476 0.072 Uiso 1 1 calc R U . . . C4 C 0.1752(5) 0.8994(5) 0.0230(4) 0.0796(17) Uani 1 1 d . . . . . H4 H 0.143566 0.908350 -0.042374 0.096 Uiso 1 1 calc R U . . . C5 C 0.1761(5) 0.9948(5) 0.0855(4) 0.0778(16) Uani 1 1 d . . . . . H5 H 0.144496 1.067567 0.062358 0.093 Uiso 1 1 calc R U . . . C6 C 0.2238(4) 0.9832(4) 0.1828(4) 0.0672(15) Uani 1 1 d . . . . . H6 H 0.225044 1.047587 0.225452 0.081 Uiso 1 1 calc R U . . . C7 C 0.2696(4) 0.8736(4) 0.2149(3) 0.0515(12) Uani 1 1 d . . . . . C8 C 0.3948(4) 0.7702(4) 0.3411(3) 0.0507(12) Uani 1 1 d . . . . . C9 C 0.4672(4) 0.7808(4) 0.4388(3) 0.0541(13) Uani 1 1 d . . . . . H9A H 0.482534 0.701409 0.466132 0.065 Uiso 1 1 calc R U . . . H9B H 0.425821 0.825238 0.481924 0.065 Uiso 1 1 calc R U . . . C10 C 0.5806(4) 0.8439(5) 0.4341(3) 0.0671(15) Uani 1 1 d . . . . . H10A H 0.635930 0.784159 0.422007 0.081 Uiso 1 1 calc R U . . . H10B H 0.569631 0.898214 0.378874 0.081 Uiso 1 1 calc R U . . . C11 C 0.6305(4) 0.9143(4) 0.5244(4) 0.0541(13) Uani 1 1 d . . . . . C12 C 0.4941(4) 0.5907(4) 0.3015(3) 0.0626(14) Uani 1 1 d . . . . . H12A H 0.531712 0.583561 0.244759 0.075 Uiso 1 1 calc R U . . . H12B H 0.550291 0.618925 0.355384 0.075 Uiso 1 1 calc R U . . . C13 C 0.4538(4) 0.4729(5) 0.3258(4) 0.0635(15) Uani 1 1 d . . . . . C14 C 0.4302(5) 0.3769(5) 0.3427(4) 0.0780(17) Uani 1 1 d . . . . . H14 H 0.410866 0.298710 0.356410 0.094 Uiso 1 1 calc R U . . . C15 C 0.2166(4) 0.5851(4) 0.2223(3) 0.0597(14) Uani 1 1 d . . . . . C16 C 0.0894(5) 0.4099(5) 0.1741(5) 0.0795(17) Uani 1 1 d . . . . . C17 C 0.1152(7) 0.3475(7) 0.2719(6) 0.186(4) Uani 1 1 d . . . . . H17A H 0.186715 0.306007 0.276713 0.279 Uiso 1 1 calc R U . . . H17B H 0.055511 0.291206 0.277746 0.279 Uiso 1 1 calc R U . . . H17C H 0.119604 0.405815 0.323172 0.279 Uiso 1 1 calc R U . . . C18 C 0.0851(6) 0.3206(6) 0.0923(6) 0.161(4) Uani 1 1 d . . . . . H18A H 0.071444 0.361865 0.030908 0.242 Uiso 1 1 calc R U . . . H18B H 0.024460 0.264456 0.095430 0.242 Uiso 1 1 calc R U . . . H18C H 0.156473 0.278617 0.098570 0.242 Uiso 1 1 calc R U . . . C19 C -0.0233(5) 0.4743(5) 0.1614(5) 0.122(3) Uani 1 1 d . . . . . H19A H -0.018834 0.539968 0.206490 0.184 Uiso 1 1 calc R U . . . H19B H -0.082049 0.419874 0.173558 0.184 Uiso 1 1 calc R U . . . H19C H -0.041136 0.504310 0.095870 0.184 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.100(3) 0.092(3) 0.039(2) -0.0081(19) 0.017(2) -0.010(2) O2 0.065(2) 0.061(2) 0.081(3) 0.002(2) -0.0026(19) -0.0118(18) O3 0.115(3) 0.112(3) 0.059(2) -0.023(2) 0.041(2) -0.045(2) N1 0.053(3) 0.063(3) 0.044(3) -0.012(2) 0.003(2) 0.008(2) N2 0.060(3) 0.052(2) 0.039(2) -0.009(2) 0.003(2) 0.006(2) N3 0.058(3) 0.052(2) 0.077(3) -0.013(2) 0.017(2) -0.010(2) C1 0.059(3) 0.055(3) 0.039(3) -0.011(2) 0.006(2) -0.007(3) C2 0.054(3) 0.053(3) 0.040(3) -0.009(3) 0.005(2) -0.003(2) C3 0.061(4) 0.073(4) 0.048(4) -0.006(3) 0.013(3) -0.004(3) C4 0.094(5) 0.090(4) 0.051(4) 0.010(4) -0.001(3) 0.018(4) C5 0.090(5) 0.071(4) 0.069(4) 0.010(3) 0.000(3) 0.012(3) C6 0.060(4) 0.067(4) 0.073(4) -0.011(3) 0.007(3) 0.006(3) C7 0.046(3) 0.058(3) 0.048(3) -0.007(3) 0.002(2) 0.001(2) C8 0.044(3) 0.063(3) 0.046(3) -0.003(3) 0.010(3) -0.001(2) C9 0.058(3) 0.065(3) 0.037(3) -0.004(2) 0.001(2) -0.003(3) C10 0.065(4) 0.090(4) 0.047(3) -0.001(3) 0.012(3) -0.013(3) C11 0.048(3) 0.057(3) 0.055(3) -0.005(3) -0.001(3) 0.005(3) C12 0.062(4) 0.070(4) 0.053(3) -0.012(3) 0.000(3) 0.005(3) C13 0.077(4) 0.054(3) 0.058(4) -0.006(3) 0.006(3) 0.002(3) C14 0.095(5) 0.070(4) 0.063(4) 0.008(3) -0.005(3) 0.003(3) C15 0.070(4) 0.060(3) 0.046(3) 0.004(3) -0.002(3) -0.008(3) C16 0.071(4) 0.062(4) 0.103(5) -0.016(4) 0.006(4) -0.020(3) C17 0.213(10) 0.161(8) 0.162(8) 0.085(7) -0.038(7) -0.126(7) C18 0.125(7) 0.118(6) 0.258(10) -0.102(7) 0.083(7) -0.064(5) C19 0.070(5) 0.127(6) 0.175(7) -0.020(5) 0.034(5) -0.022(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' 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 C8 N1 C7 122.7(4) . . ? C8 N1 H1N 118.6 . . ? C7 N1 H1N 118.6 . . ? C8 N2 C12 121.2(4) . . ? C8 N2 C1 121.4(4) . . ? C12 N2 C1 117.2(4) . . ? C15 N3 C16 125.5(4) . . ? C15 N3 H3N 117.2 . . ? C16 N3 H3N 117.2 . . ? N2 C1 C2 109.9(4) . . ? N2 C1 C15 108.9(3) . . ? C2 C1 C15 109.2(4) . . ? N2 C1 H1 109.6 . . ? C2 C1 H1 109.6 . . ? C15 C1 H1 109.6 . . ? C7 C2 C3 120.1(5) . . ? C7 C2 C1 119.0(4) . . ? C3 C2 C1 120.9(4) . . ? C4 C3 C2 119.2(5) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.7(5) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 120.4(5) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 118.4(5) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C2 C7 C6 121.3(5) . . ? C2 C7 N1 118.5(4) . . ? C6 C7 N1 120.0(4) . . ? N2 C8 N1 119.6(4) . . ? N2 C8 C9 123.2(4) . . ? N1 C8 C9 117.0(4) . . ? C8 C9 C10 112.3(4) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 115.6(4) . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C9 C10 H10B 108.4 . . ? H10A C10 H10B 107.4 . . ? O1 C11 O2 125.6(5) . . ? O1 C11 C10 118.1(4) . . ? O2 C11 C10 116.2(4) . . ? C13 C12 N2 113.1(4) . . ? C13 C12 H12A 108.9 . . ? N2 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? N2 C12 H12B 108.9 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 174.4(6) . . ? C13 C14 H14 180.0 . . ? O3 C15 N3 126.2(5) . . ? O3 C15 C1 118.9(4) . . ? N3 C15 C1 114.9(4) . . ? N3 C16 C19 109.9(5) . . ? N3 C16 C18 106.3(5) . . ? C19 C16 C18 107.8(5) . . ? N3 C16 C17 110.2(5) . . ? C19 C16 C17 111.9(6) . . ? C18 C16 C17 110.5(6) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 O1 C11 1.233(5) . ? O2 C11 1.252(5) . ? O3 C15 1.215(5) . ? N1 C8 1.321(5) . ? N1 C7 1.415(5) . ? N1 H1N 0.8600 . ? N2 C8 1.319(5) . ? N2 C12 1.471(5) . ? N2 C1 1.483(5) . ? N3 C15 1.321(5) . ? N3 C16 1.483(6) . ? N3 H3N 0.8600 . ? C1 C2 1.507(6) . ? C1 C15 1.537(6) . ? C1 H1 0.9800 . ? C2 C7 1.357(6) . ? C2 C3 1.386(6) . ? C3 C4 1.371(6) . ? C3 H3 0.9300 . ? C4 C5 1.373(6) . ? C4 H4 0.9300 . ? C5 C6 1.384(7) . ? C5 H5 0.9300 . ? C6 C7 1.383(6) . ? C6 H6 0.9300 . ? C8 C9 1.489(6) . ? C9 C10 1.528(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.516(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.457(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.142(6) . ? C14 H14 0.9300 . ? C16 C19 1.504(7) . ? C16 C18 1.506(7) . ? C16 C17 1.512(7) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 N1 H1N O2 0.86 2.15 2.987(5) 164.8 3_676 N3 H3N O2 0.86 2.14 2.987(5) 170.4 2_645 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 C8 N2 C1 C2 32.8(5) . . . . ? C12 N2 C1 C2 -150.3(4) . . . . ? C8 N2 C1 C15 -86.8(5) . . . . ? C12 N2 C1 C15 90.1(5) . . . . ? N2 C1 C2 C7 -26.9(6) . . . . ? C15 C1 C2 C7 92.5(5) . . . . ? N2 C1 C2 C3 155.3(4) . . . . ? C15 C1 C2 C3 -85.3(5) . . . . ? C7 C2 C3 C4 -0.2(7) . . . . ? C1 C2 C3 C4 177.6(4) . . . . ? C2 C3 C4 C5 -0.4(8) . . . . ? C3 C4 C5 C6 0.6(9) . . . . ? C4 C5 C6 C7 -0.3(8) . . . . ? C3 C2 C7 C6 0.5(7) . . . . ? C1 C2 C7 C6 -177.4(4) . . . . ? C3 C2 C7 N1 -176.0(4) . . . . ? C1 C2 C7 N1 6.2(6) . . . . ? C5 C6 C7 C2 -0.2(7) . . . . ? C5 C6 C7 N1 176.2(4) . . . . ? C8 N1 C7 C2 14.2(7) . . . . ? C8 N1 C7 C6 -162.3(4) . . . . ? C12 N2 C8 N1 167.2(4) . . . . ? C1 N2 C8 N1 -15.9(6) . . . . ? C12 N2 C8 C9 -8.7(6) . . . . ? C1 N2 C8 C9 168.2(4) . . . . ? C7 N1 C8 N2 -9.5(7) . . . . ? C7 N1 C8 C9 166.7(4) . . . . ? N2 C8 C9 C10 87.8(5) . . . . ? N1 C8 C9 C10 -88.2(5) . . . . ? C8 C9 C10 C11 149.8(4) . . . . ? C9 C10 C11 O1 18.1(7) . . . . ? C9 C10 C11 O2 -159.9(4) . . . . ? C8 N2 C12 C13 111.2(5) . . . . ? C1 N2 C12 C13 -65.8(5) . . . . ? C16 N3 C15 O3 -0.4(8) . . . . ? C16 N3 C15 C1 -179.9(4) . . . . ? N2 C1 C15 O3 46.7(6) . . . . ? C2 C1 C15 O3 -73.3(6) . . . . ? N2 C1 C15 N3 -133.8(4) . . . . ? C2 C1 C15 N3 106.2(5) . . . . ? C15 N3 C16 C19 66.3(7) . . . . ? C15 N3 C16 C18 -177.2(5) . . . . ? C15 N3 C16 C17 -57.5(7) . . . . ?