#------------------------------------------------------------------------------ #$Date: 2024-11-07 03:50:03 +0200 (Thu, 07 Nov 2024) $ #$Revision: 295815 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160208.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_7160208 loop_ _publ_author_name 'He, Kun' 'Zeng, Weikun' 'Yu, Xianglin' 'Zhou, Jun' 'Jin, Yi' _publ_section_title ; Direct synthesis of Enone-Hydrazones under solvent free and additives free conditions ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01578A _journal_year 2024 _chemical_formula_moiety 'C24 H22 N2 O' _chemical_formula_sum 'C24 H22 N2 O' _chemical_formula_weight 354.43 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2021-12-16 _audit_creation_method ; Olex2 1.2 (compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874) ; _audit_update_record ; 2022-07-15 deposited with the CCDC. 2024-11-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.555(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.550(19) _cell_length_b 6.415(9) _cell_length_c 21.40(3) _cell_measurement_reflns_used 602 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 16.89 _cell_measurement_theta_min 2.85 _cell_volume 1964(5) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1497 _diffrn_reflns_av_unetI/netI 0.1862 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 14294 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.250 _diffrn_reflns_theta_min 1.862 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.199 _exptl_crystal_description block _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.183 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 250 _refine_ls_number_reflns 3558 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.014 _refine_ls_R_factor_all 0.2217 _refine_ls_R_factor_gt 0.0824 _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^)+(0.0400P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1761 _refine_ls_wR_factor_ref 0.2388 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1281 _reflns_number_total 3558 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01578a2.cif _cod_data_source_block hs _cod_database_code 7160208 _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 0.996 _shelx_estimated_absorpt_t_min 0.987 _olex2_refinement_description ; 1. Others Fixed Uiso: H1(0.099) H2(0.116) H3(0.12) H4(0.116) H5(0.099) H8(0.085) H9(0.089) H12(0.079) H13(0.092) H14(0.098) H15(0.094) H16(0.082) H18(0.085) H21(0.093) H22(0.083) H23A(0.163) H23B(0.163) H23C(0.163) H24A(0.145) H24B(0.145) H24C(0.145) Fixed X: H1(0.325949) H2(0.270416) H3(0.112509) H4(0.010048) H5(0.063167) H8(0.364449) H9(0.422017) H12(0.236005) H13(0.086306) H14(-0.028659) H15(0.004742) H16(0.153207) H18(0.285716) H21(0.506962) H22(0.439166) H23A(0.398334) H23B(0.313861) H23C(0.301664) H24A(0.530786) H24B(0.437295) H24C(0.513453) Fixed Y: H1(1.208115) H2(1.489413) H3(1.537809) H4(1.309826) H5(1.035367) H8(0.893183) H9(0.628082) H12(0.649167) H13(0.720954) H14(0.470461) H15(0.150887) H16(0.072852) H18(0.127131) H21(-0.239326) H22(0.047012) H23A(- 0.192765) H23B(-0.316497) H23C(-0.081984) H24A(-0.476618) H24B(-0.529431) H24C(-0.392423) Fixed Z: H1(-0.147684) H2(-0.211414) H3(-0.24337) H4(-0.211583) H5(-0.144936) H8(-0.11942) H9(-0.056043) H12(0.092148) H13(0.108394) H14(0.086353) H15(0.048056) H16(0.03347) H18(0.161349) H21(0.080396) H22(0.026838) H23A(0.273363) H23B(0.23451) H23C(0.251912) H24A(0.163753) H24B(0.186906) H24C(0.229382) ; _shelx_res_file ; TITL HS_a.res in P-1 New:P21/n hs.res created by SHELXL-2016/6 at 10:18:05 on 16-Dec-2021 CELL 0.71073 14.5500 6.4150 21.4000 90.000 100.555 90.000 ZERR 4 0.0190 0.0090 0.0300 0.000 0.011 0.000 LATT 1 SYMM 0.50000 - X , 0.50000 + Y , 0.50000 - Z SFAC C H N O UNIT 96 88 8 4 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP 23 L.S. 5 FMAP 2 OMIT -3 50.5 PLAN -20 ACTA SIZE 0.18 0.15 0.06 BOND $H CONF REM RESI 0 WGHT 0.040000 FVAR 0.49250 O1 4 0.177745 0.824316 -0.067755 11.00000 0.06495 0.08118 = 0.10391 0.01479 0.03031 0.00487 N1 3 0.311479 0.557280 -0.020862 11.00000 0.06388 0.05606 = 0.09157 0.01117 0.01231 0.00194 N2 3 0.355433 0.395901 0.015725 11.00000 0.06309 0.05274 = 0.09309 0.00535 0.02435 0.00264 C1 1 0.261845 1.227760 -0.159911 11.00000 0.07984 0.07034 = 0.09236 0.01106 0.00595 0.00333 AFIX 43 H1 2 0.325949 1.208115 -0.147684 11.00000 -1.20000 AFIX 0 C2 1 0.228542 1.396454 -0.198499 11.00000 0.10810 0.06901 = 0.11093 0.02109 0.01391 -0.00669 AFIX 43 H2 2 0.270416 1.489413 -0.211414 11.00000 -1.20000 AFIX 0 C3 1 0.134680 1.425669 -0.217393 11.00000 0.12122 0.07205 = 0.10229 0.00920 0.01068 0.03181 AFIX 43 H3 2 0.112509 1.537809 -0.243370 11.00000 -1.20000 AFIX 0 C4 1 0.073981 1.290746 -0.198168 11.00000 0.09559 0.09633 = 0.09254 0.00290 0.00313 0.02239 AFIX 43 H4 2 0.010048 1.309826 -0.211583 11.00000 -1.20000 AFIX 0 C5 1 0.105933 1.124158 -0.158664 11.00000 0.07310 0.08143 = 0.09355 0.00486 0.01536 0.00909 AFIX 43 H5 2 0.063167 1.035367 -0.144936 11.00000 -1.20000 AFIX 0 C6 1 0.200624 1.088967 -0.139543 11.00000 0.06413 0.06393 = 0.06618 -0.00320 0.01493 0.00154 C7 1 0.233426 0.904557 -0.098716 11.00000 0.06343 0.05803 = 0.07240 -0.00882 0.02054 -0.00632 C8 1 0.325848 0.829133 -0.095000 11.00000 0.06812 0.05961 = 0.08811 0.01372 0.02366 0.00474 AFIX 43 H8 2 0.364449 0.893183 -0.119420 11.00000 -1.20000 AFIX 0 C9 1 0.360128 0.666330 -0.056975 11.00000 0.06339 0.06519 = 0.09869 0.00558 0.02532 -0.00711 AFIX 43 H9 2 0.422017 0.628082 -0.056043 11.00000 -1.20000 AFIX 0 C10 1 0.307516 0.300300 0.052454 11.00000 0.06073 0.05104 = 0.07290 -0.00657 0.01150 -0.00364 C11 1 0.210814 0.354854 0.060358 11.00000 0.05744 0.05215 = 0.07117 0.00034 0.01600 -0.00200 C12 1 0.189679 0.547978 0.083266 11.00000 0.06809 0.05513 = 0.07722 -0.00442 0.02180 -0.00243 AFIX 43 H12 2 0.236005 0.649167 0.092148 11.00000 -1.20000 AFIX 0 C13 1 0.100053 0.591237 0.093014 11.00000 0.07490 0.06296 = 0.09828 -0.00788 0.02889 0.01048 AFIX 43 H13 2 0.086306 0.720954 0.108394 11.00000 -1.20000 AFIX 0 C14 1 0.031539 0.441730 0.079868 11.00000 0.05719 0.09737 = 0.09294 -0.00238 0.02052 -0.00392 AFIX 43 H14 2 -0.028659 0.470461 0.086353 11.00000 -1.20000 AFIX 0 C15 1 0.051699 0.250538 0.057243 11.00000 0.06761 0.07450 = 0.09344 -0.00320 0.01847 -0.01120 AFIX 43 H15 2 0.004742 0.150887 0.048056 11.00000 -1.20000 AFIX 0 C16 1 0.140115 0.204254 0.047978 11.00000 0.06190 0.05906 = 0.08531 -0.00622 0.01986 -0.00151 AFIX 43 H16 2 0.153207 0.072852 0.033470 11.00000 -1.20000 AFIX 0 C17 1 0.354158 0.119355 0.087740 11.00000 0.05385 0.04831 = 0.07400 0.00097 0.01501 -0.00479 C18 1 0.331175 0.053781 0.145058 11.00000 0.07236 0.05374 = 0.08944 -0.01253 0.02170 -0.00296 AFIX 43 H18 2 0.285716 0.127131 0.161349 11.00000 -1.20000 AFIX 0 C19 1 0.373494 -0.117261 0.179021 11.00000 0.08138 0.06052 = 0.07308 0.00354 0.01013 -0.01109 C20 1 0.440060 -0.230601 0.154214 11.00000 0.07203 0.05141 = 0.08211 0.00798 -0.00323 -0.00586 C21 1 0.462454 -0.164891 0.097340 11.00000 0.06317 0.06059 = 0.10700 0.00582 0.01350 0.00916 AFIX 43 H21 2 0.506962 -0.239326 0.080396 11.00000 -1.20000 AFIX 0 C22 1 0.421349 0.006983 0.064653 11.00000 0.06289 0.06305 = 0.08499 0.00487 0.01977 -0.00024 AFIX 43 H22 2 0.439166 0.047012 0.026838 11.00000 -1.20000 AFIX 0 C23 1 0.344162 -0.183136 0.240291 11.00000 0.14647 0.09632 = 0.08780 0.01597 0.03262 0.00326 AFIX 137 H23A 2 0.398334 -0.192765 0.273363 11.00000 -1.50000 H23B 2 0.313861 -0.316497 0.234510 11.00000 -1.50000 H23C 2 0.301664 -0.081984 0.251912 11.00000 -1.50000 AFIX 0 C24 1 0.484451 -0.425017 0.186512 11.00000 0.09488 0.06937 = 0.11863 0.02178 0.00201 -0.00206 AFIX 137 H24A 2 0.530786 -0.476618 0.163753 11.00000 -1.50000 H24B 2 0.437295 -0.529431 0.186906 11.00000 -1.50000 H24C 2 0.513453 -0.392423 0.229382 11.00000 -1.50000 REM ##### AFIX 0 H1D 2 0.250348 0.588706 -0.026212 11.00000 0.11335 HKLF 4 1 0.0000 1.0000 0.0000 1.0000 0.0000 0.0000 0.0000 0.0000 -1.0000 REM HS_a.res in P-1 New:P21/n REM R1 = 0.0824 for 1281 Fo > 4sig(Fo) and 0.2217 for all 3558 data REM 250 parameters refined using 0 restraints END WGHT 0.0995 0.0000 REM Highest difference peak 0.183, deepest hole -0.238, 1-sigma level 0.055 Q1 1 0.4000 0.7459 -0.1382 11.00000 0.05 0.18 Q2 1 0.2246 0.1563 0.1356 11.00000 0.05 0.18 Q3 1 0.4199 0.7964 -0.1297 11.00000 0.05 0.17 Q4 1 0.3291 0.6547 0.0974 11.00000 0.05 0.17 Q5 1 0.4123 0.0380 0.0047 11.00000 0.05 0.16 Q6 1 0.3390 1.2800 -0.0979 11.00000 0.05 0.16 Q7 1 0.3030 1.3811 -0.2782 11.00000 0.05 0.15 Q8 1 0.4016 0.0885 0.2422 11.00000 0.05 0.15 Q9 1 0.1379 0.7973 0.0305 11.00000 0.05 0.15 Q10 1 0.3141 0.3405 0.3319 11.00000 0.05 0.15 Q11 1 0.2596 1.2119 -0.2509 11.00000 0.05 0.15 Q12 1 0.1628 0.9785 0.0022 11.00000 0.05 0.15 Q13 1 0.3549 0.1157 0.2737 11.00000 0.05 0.15 Q14 1 0.3216 1.0402 -0.1942 11.00000 0.05 0.15 Q15 1 0.1178 0.6703 -0.0261 11.00000 0.05 0.15 Q16 1 0.3732 0.1544 -0.0196 11.00000 0.05 0.14 Q17 1 0.3052 0.2631 0.2482 11.00000 0.05 0.14 Q18 1 0.2839 0.2520 0.1700 11.00000 0.05 0.14 Q19 1 0.5170 -0.1850 0.2167 11.00000 0.05 0.14 Q20 1 0.1663 1.4570 -0.1374 11.00000 0.05 0.14 ; _shelx_res_checksum 33580 _shelx_shelxl_version_number 2016/6 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 0.1777(2) 0.8243(5) -0.06776(17) 0.0815(10) Uani 1 1 d . . . . . N1 N 0.3115(3) 0.5573(6) -0.0209(2) 0.0707(12) Uani 1 1 d . . . . . N2 N 0.3554(3) 0.3959(6) 0.0157(2) 0.0684(11) Uani 1 1 d . . . . . C1 C 0.2618(4) 1.2278(8) -0.1599(3) 0.0821(16) Uani 1 1 d . . . . . H1 H 0.325949 1.208115 -0.147684 0.099 Uiso 1 1 calc R U . . . C2 C 0.2285(5) 1.3965(8) -0.1985(3) 0.0968(18) Uani 1 1 d . . . . . H2 H 0.270416 1.489413 -0.211414 0.116 Uiso 1 1 calc R U . . . C3 C 0.1347(6) 1.4257(9) -0.2174(3) 0.0998(19) Uani 1 1 d . . . . . H3 H 0.112509 1.537809 -0.243370 0.120 Uiso 1 1 calc R U . . . C4 C 0.0740(5) 1.2907(10) -0.1982(3) 0.0966(19) Uani 1 1 d . . . . . H4 H 0.010048 1.309826 -0.211583 0.116 Uiso 1 1 calc R U . . . C5 C 0.1059(4) 1.1242(8) -0.1587(3) 0.0827(16) Uani 1 1 d . . . . . H5 H 0.063167 1.035367 -0.144936 0.099 Uiso 1 1 calc R U . . . C6 C 0.2006(3) 1.0890(7) -0.1395(2) 0.0644(13) Uani 1 1 d . . . . . C7 C 0.2334(3) 0.9046(7) -0.0987(2) 0.0636(13) Uani 1 1 d . . . . . C8 C 0.3258(3) 0.8291(7) -0.0950(2) 0.0708(14) Uani 1 1 d . . . . . H8 H 0.364449 0.893183 -0.119420 0.085 Uiso 1 1 calc R U . . . C9 C 0.3601(4) 0.6663(8) -0.0570(3) 0.0744(14) Uani 1 1 d . . . . . H9 H 0.422017 0.628082 -0.056043 0.089 Uiso 1 1 calc R U . . . C10 C 0.3075(3) 0.3003(7) 0.0525(2) 0.0616(13) Uani 1 1 d . . . . . C11 C 0.2108(3) 0.3549(7) 0.0604(2) 0.0597(12) Uani 1 1 d . . . . . C12 C 0.1897(3) 0.5480(7) 0.0833(2) 0.0657(13) Uani 1 1 d . . . . . H12 H 0.236005 0.649167 0.092148 0.079 Uiso 1 1 calc R U . . . C13 C 0.1001(4) 0.5912(8) 0.0930(2) 0.0771(15) Uani 1 1 d . . . . . H13 H 0.086306 0.720954 0.108394 0.092 Uiso 1 1 calc R U . . . C14 C 0.0315(3) 0.4417(9) 0.0799(2) 0.0816(16) Uani 1 1 d . . . . . H14 H -0.028659 0.470461 0.086353 0.098 Uiso 1 1 calc R U . . . C15 C 0.0517(4) 0.2505(9) 0.0572(2) 0.0780(15) Uani 1 1 d . . . . . H15 H 0.004742 0.150887 0.048056 0.094 Uiso 1 1 calc R U . . . C16 C 0.1401(3) 0.2043(7) 0.0480(2) 0.0679(14) Uani 1 1 d . . . . . H16 H 0.153207 0.072852 0.033470 0.082 Uiso 1 1 calc R U . . . C17 C 0.3542(3) 0.1194(7) 0.0877(2) 0.0583(12) Uani 1 1 d . . . . . C18 C 0.3312(3) 0.0538(7) 0.1451(3) 0.0710(14) Uani 1 1 d . . . . . H18 H 0.285716 0.127131 0.161349 0.085 Uiso 1 1 calc R U . . . C19 C 0.3735(4) -0.1173(8) 0.1790(2) 0.0722(14) Uani 1 1 d . . . . . C20 C 0.4401(4) -0.2306(7) 0.1542(3) 0.0707(15) Uani 1 1 d . . . . . C21 C 0.4625(3) -0.1649(8) 0.0973(3) 0.0772(15) Uani 1 1 d . . . . . H21 H 0.506962 -0.239326 0.080396 0.093 Uiso 1 1 calc R U . . . C22 C 0.4213(3) 0.0070(7) 0.0647(2) 0.0695(14) Uani 1 1 d . . . . . H22 H 0.439166 0.047012 0.026838 0.083 Uiso 1 1 calc R U . . . C23 C 0.3442(4) -0.1831(9) 0.2403(3) 0.109(2) Uani 1 1 d . . . . . H23A H 0.398334 -0.192765 0.273363 0.163 Uiso 1 1 calc R U . . . H23B H 0.313861 -0.316497 0.234510 0.163 Uiso 1 1 calc R U . . . H23C H 0.301664 -0.081984 0.251912 0.163 Uiso 1 1 calc R U . . . C24 C 0.4845(4) -0.4250(7) 0.1865(3) 0.0965(19) Uani 1 1 d . . . . . H24A H 0.530786 -0.476618 0.163753 0.145 Uiso 1 1 calc R U . . . H24B H 0.437295 -0.529431 0.186906 0.145 Uiso 1 1 calc R U . . . H24C H 0.513453 -0.392423 0.229382 0.145 Uiso 1 1 calc R U . . . H1D H 0.250(4) 0.589(8) -0.026(3) 0.11(2) Uiso 1 1 d . . . . . 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 0.065(2) 0.081(2) 0.104(3) 0.015(2) 0.030(2) 0.0049(19) N1 0.064(3) 0.056(3) 0.092(3) 0.011(2) 0.012(3) 0.002(2) N2 0.063(3) 0.053(2) 0.093(3) 0.005(2) 0.024(2) 0.003(2) C1 0.080(4) 0.070(4) 0.092(4) 0.011(3) 0.006(3) 0.003(3) C2 0.108(5) 0.069(4) 0.111(5) 0.021(3) 0.014(4) -0.007(4) C3 0.121(6) 0.072(4) 0.102(5) 0.009(4) 0.011(4) 0.032(4) C4 0.096(5) 0.096(5) 0.093(4) 0.003(4) 0.003(4) 0.022(4) C5 0.073(4) 0.081(4) 0.094(4) 0.005(3) 0.015(3) 0.009(3) C6 0.064(3) 0.064(3) 0.066(3) -0.003(3) 0.015(3) 0.002(3) C7 0.063(3) 0.058(3) 0.072(3) -0.009(3) 0.021(3) -0.006(3) C8 0.068(3) 0.060(3) 0.088(4) 0.014(3) 0.024(3) 0.005(3) C9 0.063(3) 0.065(3) 0.099(4) 0.006(3) 0.025(3) -0.007(3) C10 0.061(3) 0.051(3) 0.073(3) -0.007(3) 0.012(3) -0.004(3) C11 0.057(3) 0.052(3) 0.071(3) 0.000(2) 0.016(2) -0.002(3) C12 0.068(3) 0.055(3) 0.077(3) -0.004(3) 0.022(3) -0.002(3) C13 0.075(4) 0.063(3) 0.098(4) -0.008(3) 0.029(3) 0.010(3) C14 0.057(3) 0.097(4) 0.093(4) -0.002(3) 0.021(3) -0.004(3) C15 0.068(4) 0.074(4) 0.093(4) -0.003(3) 0.018(3) -0.011(3) C16 0.062(3) 0.059(3) 0.085(4) -0.006(3) 0.020(3) -0.002(3) C17 0.054(3) 0.048(3) 0.074(3) 0.001(3) 0.015(3) -0.005(2) C18 0.072(3) 0.054(3) 0.089(4) -0.013(3) 0.022(3) -0.003(3) C19 0.081(4) 0.061(3) 0.073(4) 0.004(3) 0.010(3) -0.011(3) C20 0.072(4) 0.051(3) 0.082(4) 0.008(3) -0.003(3) -0.006(3) C21 0.063(3) 0.061(3) 0.107(4) 0.006(3) 0.013(3) 0.009(3) C22 0.063(3) 0.063(3) 0.085(4) 0.005(3) 0.020(3) 0.000(3) C23 0.146(6) 0.096(4) 0.088(4) 0.016(3) 0.033(4) 0.003(4) C24 0.095(4) 0.069(4) 0.119(5) 0.022(3) 0.002(4) -0.002(3) 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 N2 N1 H1D 126(4) . . ? C9 N1 N2 118.7(5) . . ? C9 N1 H1D 115(4) . . ? C10 N2 N1 117.0(4) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C6 C1 C2 120.8(5) . . ? C1 C2 H2 119.9 . . ? C3 C2 C1 120.2(6) . . ? C3 C2 H2 119.9 . . ? C2 C3 H3 120.1 . . ? C4 C3 C2 119.7(6) . . ? C4 C3 H3 120.1 . . ? C3 C4 H4 119.6 . . ? C3 C4 C5 120.9(6) . . ? C5 C4 H4 119.6 . . ? C4 C5 H5 119.7 . . ? C6 C5 C4 120.7(5) . . ? C6 C5 H5 119.7 . . ? C1 C6 C7 122.5(4) . . ? C5 C6 C1 117.7(5) . . ? C5 C6 C7 119.7(5) . . ? O1 C7 C6 117.9(4) . . ? O1 C7 C8 122.1(5) . . ? C8 C7 C6 120.0(5) . . ? C7 C8 H8 118.8 . . ? C9 C8 C7 122.4(5) . . ? C9 C8 H8 118.8 . . ? N1 C9 C8 124.9(5) . . ? N1 C9 H9 117.6 . . ? C8 C9 H9 117.6 . . ? N2 C10 C11 125.6(4) . . ? N2 C10 C17 115.7(4) . . ? C17 C10 C11 118.7(4) . . ? C12 C11 C10 121.7(4) . . ? C12 C11 C16 118.7(4) . . ? C16 C11 C10 119.5(4) . . ? C11 C12 H12 119.7 . . ? C13 C12 C11 120.5(4) . . ? C13 C12 H12 119.7 . . ? C12 C13 H13 120.1 . . ? C14 C13 C12 119.8(5) . . ? C14 C13 H13 120.1 . . ? C13 C14 H14 119.9 . . ? C15 C14 C13 120.2(5) . . ? C15 C14 H14 119.9 . . ? C14 C15 H15 119.6 . . ? C16 C15 C14 120.9(5) . . ? C16 C15 H15 119.6 . . ? C11 C16 H16 120.0 . . ? C15 C16 C11 120.0(5) . . ? C15 C16 H16 120.0 . . ? C18 C17 C10 121.6(5) . . ? C22 C17 C10 121.1(5) . . ? C22 C17 C18 117.3(4) . . ? C17 C18 H18 118.6 . . ? C17 C18 C19 122.8(5) . . ? C19 C18 H18 118.6 . . ? C18 C19 C23 120.3(5) . . ? C20 C19 C18 118.9(5) . . ? C20 C19 C23 120.8(5) . . ? C19 C20 C24 121.7(5) . . ? C21 C20 C19 118.0(5) . . ? C21 C20 C24 120.3(5) . . ? C20 C21 H21 118.7 . . ? C22 C21 C20 122.6(5) . . ? C22 C21 H21 118.7 . . ? C17 C22 C21 120.4(5) . . ? C17 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 C7 1.248(5) . ? N1 N2 1.382(5) . ? N1 C9 1.337(6) . ? N1 H1D 0.90(5) . ? N2 C10 1.296(5) . ? C1 H1 0.9300 . ? C1 C2 1.393(7) . ? C1 C6 1.385(6) . ? C2 H2 0.9300 . ? C2 C3 1.364(8) . ? C3 H3 0.9300 . ? C3 C4 1.353(8) . ? C4 H4 0.9300 . ? C4 C5 1.389(7) . ? C5 H5 0.9300 . ? C5 C6 1.382(6) . ? C6 C7 1.496(6) . ? C7 C8 1.418(6) . ? C8 H8 0.9300 . ? C8 C9 1.361(6) . ? C9 H9 0.9300 . ? C10 C11 1.489(6) . ? C10 C17 1.480(6) . ? C11 C12 1.387(6) . ? C11 C16 1.401(6) . ? C12 H12 0.9300 . ? C12 C13 1.386(6) . ? C13 H13 0.9300 . ? C13 C14 1.375(6) . ? C14 H14 0.9300 . ? C14 C15 1.370(6) . ? C15 H15 0.9300 . ? C15 C16 1.370(6) . ? C16 H16 0.9300 . ? C17 C18 1.394(6) . ? C17 C22 1.377(6) . ? C18 H18 0.9300 . ? C18 C19 1.395(6) . ? C19 C20 1.392(7) . ? C19 C23 1.512(7) . ? C20 C21 1.382(7) . ? C20 C24 1.512(6) . ? C21 H21 0.9300 . ? C21 C22 1.382(6) . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 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 O1 C7 C8 C9 -0.8(7) . . . . ? N1 N2 C10 C11 -2.5(7) . . . . ? N1 N2 C10 C17 176.0(4) . . . . ? N2 N1 C9 C8 -179.7(4) . . . . ? N2 C10 C11 C12 -61.0(6) . . . . ? N2 C10 C11 C16 122.7(5) . . . . ? N2 C10 C17 C18 154.3(4) . . . . ? N2 C10 C17 C22 -26.6(6) . . . . ? C1 C2 C3 C4 0.4(9) . . . . ? C1 C6 C7 O1 159.6(5) . . . . ? C1 C6 C7 C8 -19.1(7) . . . . ? C2 C1 C6 C5 -0.2(8) . . . . ? C2 C1 C6 C7 179.3(5) . . . . ? C2 C3 C4 C5 0.9(9) . . . . ? C3 C4 C5 C6 -1.9(9) . . . . ? C4 C5 C6 C1 1.5(8) . . . . ? C4 C5 C6 C7 -178.0(5) . . . . ? C5 C6 C7 O1 -21.0(7) . . . . ? C5 C6 C7 C8 160.4(5) . . . . ? C6 C1 C2 C3 -0.8(9) . . . . ? C6 C7 C8 C9 177.8(4) . . . . ? C7 C8 C9 N1 1.9(8) . . . . ? C9 N1 N2 C10 176.7(4) . . . . ? C10 C11 C12 C13 -176.9(4) . . . . ? C10 C11 C16 C15 177.7(4) . . . . ? C10 C17 C18 C19 179.5(4) . . . . ? C10 C17 C22 C21 -178.3(4) . . . . ? C11 C10 C17 C18 -27.1(6) . . . . ? C11 C10 C17 C22 152.0(4) . . . . ? C11 C12 C13 C14 0.0(7) . . . . ? C12 C11 C16 C15 1.4(7) . . . . ? C12 C13 C14 C15 0.0(8) . . . . ? C13 C14 C15 C16 0.7(8) . . . . ? C14 C15 C16 C11 -1.4(7) . . . . ? C16 C11 C12 C13 -0.7(7) . . . . ? C17 C10 C11 C12 120.5(5) . . . . ? C17 C10 C11 C16 -55.8(6) . . . . ? C17 C18 C19 C20 -1.4(7) . . . . ? C17 C18 C19 C23 -178.8(4) . . . . ? C18 C17 C22 C21 0.8(6) . . . . ? C18 C19 C20 C21 1.3(7) . . . . ? C18 C19 C20 C24 -176.3(4) . . . . ? C19 C20 C21 C22 -0.2(7) . . . . ? C20 C21 C22 C17 -1.0(7) . . . . ? C22 C17 C18 C19 0.3(7) . . . . ? C23 C19 C20 C21 178.7(5) . . . . ? C23 C19 C20 C24 1.0(7) . . . . ? C24 C20 C21 C22 177.5(4) . . . . ?