#------------------------------------------------------------------------------ #$Date: 2026-03-27 01:45:35 +0000 (Fri, 27 Mar 2026) $ #$Revision: 305194 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064355.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_7064355 loop_ _publ_author_name 'Kumari, Sonu' 'Biswas, Napur' 'Thirumoorthi, Ramalingam' 'Roy, Bibhisan' 'Rajagopala Reddy, S.' 'Bhanuchandra, M.' 'Bhanuchandra, M.' _publ_section_title ; 4-Arylpyrazole-Decorated Dibenzofuran: Synthesis, Characterization, Optical Studies and Computational Analysis ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D6NJ00832A _journal_year 2026 _chemical_formula_moiety 'C30 H20 N4 O' _chemical_formula_sum 'C30 H20 N4 O' _chemical_formula_weight 452.50 _chemical_name_systematic '4-phenylpyrazole-dibenzofuran 6a' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/4 _audit_update_record ; 2025-07-19 deposited with the CCDC. 2026-03-25 downloaded from the CCDC. ; _cell_angle_alpha 83.04 _cell_angle_beta 69.0690(10) _cell_angle_gamma 69.0030(10) _cell_formula_units_Z 2 _cell_length_a 9.40300(10) _cell_length_b 10.11640(10) _cell_length_c 13.04550(10) _cell_measurement_reflns_used 33299 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 74.0460 _cell_measurement_theta_min 3.6050 _cell_volume 1082.06(2) _computing_cell_refinement 'CrysAlisPro 1.171.43.108a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro 1.171.43.108a (Rigaku OD, 2024)' _computing_data_reduction 'CrysAlisPro 1.171.43.108a (Rigaku OD, 2024)' _computing_structure_refinement 'SHELXL-2016/4 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.946 _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_unetI/netI 0.0052 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.946 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 38993 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.946 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.751 _diffrn_reflns_theta_min 3.628 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.685 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.389 _exptl_crystal_description Needle _exptl_crystal_F_000 472 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.140 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.090 _refine_diff_density_max 0.188 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 316 _refine_ls_number_reflns 4211 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0329 _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^)+(0.0370P)^2^+0.3969P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0807 _refine_ls_wR_factor_ref 0.0809 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4151 _reflns_number_total 4211 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj00832a2.cif _cod_data_source_block shelx _cod_database_code 7064355 _shelx_shelxl_version_number 2016/4 _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 0.910 _shelx_estimated_absorpt_t_max 0.941 _shelx_res_file ; TITL sj-205-3_auto_a.res in P-1 shelx.res created by SHELXL-2016/4 at 12:20:58 on 18-Feb-2025 CELL 1.54184 9.4030 10.1164 13.0455 83.044 69.069 69.003 ZERR 2.00 0.0001 0.0001 0.0001 0.000 0.001 0.001 LATT 1 SFAC C H N O UNIT 60 40 8 2 MERG 2 FMAP 2 PLAN 1 SIZE 0.14 0.12 0.09 BOND $H CONF ACTA L.S. 4 TEMP -173.00 WGHT 0.037000 0.396900 FVAR 0.42300 C1 1 0.166510 0.504121 0.578771 11.00000 0.02614 0.02049 = 0.02663 -0.00063 -0.00966 -0.00931 C2 1 0.278933 0.554300 0.497846 11.00000 0.02175 0.02049 = 0.02247 -0.00019 -0.00814 -0.00572 C3 1 0.316012 0.665931 0.522640 11.00000 0.02215 0.02168 = 0.02346 0.00028 -0.00769 -0.00789 AFIX 43 H3 2 0.393584 0.700920 0.469471 11.00000 -1.20000 AFIX 0 C4 1 0.235745 0.723961 0.627509 11.00000 0.02272 0.02034 = 0.02457 -0.00067 -0.00946 -0.00713 C5 1 0.123200 0.671588 0.707287 11.00000 0.02655 0.02597 = 0.02279 -0.00291 -0.00532 -0.00949 AFIX 43 H5 2 0.071060 0.713205 0.778520 11.00000 -1.20000 AFIX 0 C6 1 0.086939 0.560127 0.683782 11.00000 0.02724 0.02668 = 0.02456 -0.00010 -0.00454 -0.01231 AFIX 43 H6 2 0.010936 0.523843 0.737315 11.00000 -1.20000 AFIX 0 C7 1 0.329725 0.468726 0.400830 11.00000 0.02232 0.01951 = 0.02561 -0.00055 -0.01017 -0.00590 C8 1 0.244028 0.374176 0.432982 11.00000 0.02476 0.02302 = 0.02386 -0.00121 -0.00640 -0.00834 C9 1 0.258495 0.273360 0.363995 11.00000 0.03045 0.02499 = 0.03105 -0.00202 -0.00801 -0.01418 AFIX 43 H9 2 0.198688 0.210424 0.388342 11.00000 -1.20000 AFIX 0 C10 1 0.364222 0.268479 0.257802 11.00000 0.02948 0.02408 = 0.02771 -0.00464 -0.00882 -0.01033 AFIX 43 H10 2 0.379306 0.199688 0.207829 11.00000 -1.20000 AFIX 0 C11 1 0.449704 0.363775 0.222692 11.00000 0.02168 0.02269 = 0.02339 -0.00092 -0.00818 -0.00603 C12 1 0.434745 0.464524 0.292827 11.00000 0.02238 0.02083 = 0.02523 -0.00023 -0.00919 -0.00752 AFIX 43 H12 2 0.493638 0.528165 0.268340 11.00000 -1.20000 AFIX 0 C13 1 0.348186 1.016515 0.629808 11.00000 0.02776 0.02730 = 0.02487 -0.00216 -0.00544 -0.01454 AFIX 43 H13 2 0.396926 1.085320 0.595299 11.00000 -1.20000 AFIX 0 C14 1 0.267874 1.012577 0.743972 11.00000 0.02122 0.02160 = 0.02395 -0.00083 -0.00772 -0.00682 C15 1 0.216988 0.897913 0.756555 11.00000 0.02437 0.02193 = 0.02076 -0.00093 -0.00698 -0.00742 AFIX 43 H15 2 0.158312 0.864751 0.823826 11.00000 -1.20000 AFIX 0 C16 1 0.240127 1.107922 0.830998 11.00000 0.01831 0.02386 = 0.02387 -0.00252 -0.00626 -0.00689 C17 1 0.240832 1.246225 0.807703 11.00000 0.02322 0.02659 = 0.02443 -0.00045 -0.00674 -0.01150 AFIX 43 H17 2 0.262351 1.278415 0.734060 11.00000 -1.20000 AFIX 0 C18 1 0.210580 1.337580 0.890443 11.00000 0.02430 0.02514 = 0.03274 -0.00317 -0.00809 -0.01192 AFIX 43 H18 2 0.211060 1.431414 0.873145 11.00000 -1.20000 AFIX 0 C19 1 0.179641 1.291575 0.998456 11.00000 0.02150 0.03085 = 0.02888 -0.00923 -0.00741 -0.00826 AFIX 43 H19 2 0.157876 1.354026 1.055257 11.00000 -1.20000 AFIX 0 C20 1 0.180725 1.153699 1.022893 11.00000 0.02582 0.03148 = 0.02322 -0.00168 -0.00817 -0.00737 AFIX 43 H20 2 0.161445 1.121347 1.096430 11.00000 -1.20000 AFIX 0 C21 1 0.209902 1.063080 0.940161 11.00000 0.02663 0.02335 = 0.02621 -0.00012 -0.00867 -0.00723 AFIX 43 H21 2 0.209350 0.969329 0.957866 11.00000 -1.20000 AFIX 0 C22 1 0.547959 0.297036 0.025842 11.00000 0.02290 0.02630 = 0.02520 -0.00426 -0.00918 -0.00872 AFIX 43 H22 2 0.459977 0.271704 0.025785 11.00000 -1.20000 AFIX 0 C23 1 0.687637 0.285114 -0.061644 11.00000 0.02295 0.01965 = 0.02423 0.00070 -0.00979 -0.00698 C24 1 0.775890 0.338165 -0.019505 11.00000 0.02664 0.02667 = 0.02395 0.00138 -0.00836 -0.01375 AFIX 43 H24 2 0.878952 0.344934 -0.061380 11.00000 -1.20000 AFIX 0 C25 1 0.736093 0.219459 -0.169004 11.00000 0.02254 0.01924 = 0.02314 0.00076 -0.00947 -0.00584 C26 1 0.641454 0.151539 -0.188291 11.00000 0.02325 0.02649 = 0.02504 -0.00101 -0.00611 -0.01044 AFIX 43 H26 2 0.544134 0.150184 -0.132073 11.00000 -1.20000 AFIX 0 C27 1 0.687991 0.086439 -0.288184 11.00000 0.02836 0.02656 = 0.02925 -0.00201 -0.01126 -0.01191 AFIX 43 H27 2 0.621475 0.042428 -0.300375 11.00000 -1.20000 AFIX 0 C28 1 0.831191 0.085104 -0.370574 11.00000 0.02925 0.02773 = 0.02360 -0.00379 -0.00876 -0.00804 AFIX 43 H28 2 0.863871 0.039067 -0.438643 11.00000 -1.20000 AFIX 0 C29 1 0.926061 0.151533 -0.352644 11.00000 0.02452 0.03485 = 0.02536 -0.00176 -0.00468 -0.01109 AFIX 43 H29 2 1.024322 0.150900 -0.408689 11.00000 -1.20000 AFIX 0 C30 1 0.878401 0.219097 -0.253188 11.00000 0.02475 0.02876 = 0.02759 0.00009 -0.00974 -0.01216 AFIX 43 H30 2 0.943638 0.265651 -0.242414 11.00000 -1.20000 AFIX 0 N1 3 0.265611 0.840944 0.655826 11.00000 0.02364 0.02182 = 0.02185 -0.00104 -0.00609 -0.00927 N2 3 0.347918 0.913082 0.576036 11.00000 0.02820 0.02932 = 0.02325 -0.00147 -0.00365 -0.01593 N3 3 0.557722 0.351177 0.112070 11.00000 0.02268 0.02302 = 0.02372 -0.00190 -0.00829 -0.00866 N4 3 0.698721 0.377649 0.085387 11.00000 0.02826 0.02714 = 0.02546 0.00088 -0.00939 -0.01550 O1 4 0.144137 0.393507 0.541476 11.00000 0.03209 0.02577 = 0.02506 -0.00314 -0.00468 -0.01518 HKLF 4 REM sj-205-3_auto_a.res in P-1 REM R1 = 0.0329 for 4151 Fo > 4sig(Fo) and 0.0333 for all 4211 data REM 316 parameters refined using 0 restraints END WGHT 0.0370 0.3969 REM Highest difference peak 0.188, deepest hole -0.243, 1-sigma level 0.041 Q1 1 0.7101 0.2503 -0.1169 11.00000 0.05 0.19 ; _shelx_res_checksum 35092 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 C1 C 0.16651(13) 0.50412(11) 0.57877(9) 0.0237(2) Uani 1 1 d . . . . . C2 C 0.27893(12) 0.55430(11) 0.49785(8) 0.0218(2) Uani 1 1 d . . . . . C3 C 0.31601(12) 0.66593(11) 0.52264(9) 0.0223(2) Uani 1 1 d . . . . . H3 H 0.393584 0.700920 0.469471 0.027 Uiso 1 1 calc R U . . . C4 C 0.23575(12) 0.72396(11) 0.62751(9) 0.0221(2) Uani 1 1 d . . . . . C5 C 0.12320(13) 0.67159(11) 0.70729(9) 0.0255(2) Uani 1 1 d . . . . . H5 H 0.071060 0.713205 0.778520 0.031 Uiso 1 1 calc R U . . . C6 C 0.08694(13) 0.56013(12) 0.68378(9) 0.0264(2) Uani 1 1 d . . . . . H6 H 0.010936 0.523843 0.737315 0.032 Uiso 1 1 calc R U . . . C7 C 0.32972(12) 0.46873(11) 0.40083(9) 0.0222(2) Uani 1 1 d . . . . . C8 C 0.24403(13) 0.37418(11) 0.43298(9) 0.0242(2) Uani 1 1 d . . . . . C9 C 0.25850(14) 0.27336(12) 0.36399(9) 0.0279(2) Uani 1 1 d . . . . . H9 H 0.198688 0.210424 0.388342 0.034 Uiso 1 1 calc R U . . . C10 C 0.36422(14) 0.26848(11) 0.25780(9) 0.0265(2) Uani 1 1 d . . . . . H10 H 0.379306 0.199688 0.207829 0.032 Uiso 1 1 calc R U . . . C11 C 0.44970(12) 0.36378(11) 0.22269(9) 0.0228(2) Uani 1 1 d . . . . . C12 C 0.43474(12) 0.46452(11) 0.29283(9) 0.0224(2) Uani 1 1 d . . . . . H12 H 0.493638 0.528165 0.268340 0.027 Uiso 1 1 calc R U . . . C13 C 0.34819(13) 1.01652(12) 0.62981(9) 0.0259(2) Uani 1 1 d . . . . . H13 H 0.396926 1.085320 0.595299 0.031 Uiso 1 1 calc R U . . . C14 C 0.26787(12) 1.01258(11) 0.74397(9) 0.0223(2) Uani 1 1 d . . . . . C15 C 0.21699(13) 0.89791(11) 0.75655(8) 0.0226(2) Uani 1 1 d . . . . . H15 H 0.158312 0.864751 0.823826 0.027 Uiso 1 1 calc R U . . . C16 C 0.24013(12) 1.10792(11) 0.83100(9) 0.0221(2) Uani 1 1 d . . . . . C17 C 0.24083(13) 1.24623(11) 0.80770(9) 0.0242(2) Uani 1 1 d . . . . . H17 H 0.262351 1.278415 0.734060 0.029 Uiso 1 1 calc R U . . . C18 C 0.21058(13) 1.33758(12) 0.89044(9) 0.0265(2) Uani 1 1 d . . . . . H18 H 0.211060 1.431414 0.873145 0.032 Uiso 1 1 calc R U . . . C19 C 0.17964(13) 1.29157(12) 0.99846(9) 0.0267(2) Uani 1 1 d . . . . . H19 H 0.157876 1.354026 1.055257 0.032 Uiso 1 1 calc R U . . . C20 C 0.18073(13) 1.15370(12) 1.02289(9) 0.0274(2) Uani 1 1 d . . . . . H20 H 0.161445 1.121347 1.096430 0.033 Uiso 1 1 calc R U . . . C21 C 0.20990(13) 1.06308(11) 0.94016(9) 0.0258(2) Uani 1 1 d . . . . . H21 H 0.209350 0.969329 0.957866 0.031 Uiso 1 1 calc R U . . . C22 C 0.54796(13) 0.29704(11) 0.02584(9) 0.0240(2) Uani 1 1 d . . . . . H22 H 0.459977 0.271704 0.025785 0.029 Uiso 1 1 calc R U . . . C23 C 0.68764(12) 0.28511(11) -0.06164(9) 0.0219(2) Uani 1 1 d . . . . . C24 C 0.77589(13) 0.33817(11) -0.01951(9) 0.0246(2) Uani 1 1 d . . . . . H24 H 0.878952 0.344934 -0.061380 0.029 Uiso 1 1 calc R U . . . C25 C 0.73609(12) 0.21946(10) -0.16900(8) 0.0216(2) Uani 1 1 d . . . . . C26 C 0.64145(13) 0.15154(11) -0.18829(9) 0.0248(2) Uani 1 1 d . . . . . H26 H 0.544134 0.150184 -0.132073 0.030 Uiso 1 1 calc R U . . . C27 C 0.68799(13) 0.08644(12) -0.28818(9) 0.0267(2) Uani 1 1 d . . . . . H27 H 0.621475 0.042428 -0.300375 0.032 Uiso 1 1 calc R U . . . C28 C 0.83119(14) 0.08510(12) -0.37057(9) 0.0270(2) Uani 1 1 d . . . . . H28 H 0.863871 0.039067 -0.438643 0.032 Uiso 1 1 calc R U . . . C29 C 0.92606(14) 0.15153(12) -0.35264(9) 0.0289(2) Uani 1 1 d . . . . . H29 H 1.024322 0.150900 -0.408689 0.035 Uiso 1 1 calc R U . . . C30 C 0.87840(13) 0.21910(12) -0.25319(9) 0.0259(2) Uani 1 1 d . . . . . H30 H 0.943638 0.265651 -0.242414 0.031 Uiso 1 1 calc R U . . . N1 N 0.26561(11) 0.84094(9) 0.65583(7) 0.02234(19) Uani 1 1 d . . . . . N2 N 0.34792(11) 0.91308(10) 0.57604(7) 0.0264(2) Uani 1 1 d . . . . . N3 N 0.55772(11) 0.35118(9) 0.11207(7) 0.02256(19) Uani 1 1 d . . . . . N4 N 0.69872(11) 0.37765(10) 0.08539(7) 0.0252(2) Uani 1 1 d . . . . . O1 O 0.14414(9) 0.39351(8) 0.54148(6) 0.02722(18) Uani 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 C1 0.0261(5) 0.0205(5) 0.0266(5) -0.0006(4) -0.0097(4) -0.0093(4) C2 0.0217(5) 0.0205(5) 0.0225(5) -0.0002(4) -0.0081(4) -0.0057(4) C3 0.0222(5) 0.0217(5) 0.0235(5) 0.0003(4) -0.0077(4) -0.0079(4) C4 0.0227(5) 0.0203(5) 0.0246(5) -0.0007(4) -0.0095(4) -0.0071(4) C5 0.0266(5) 0.0260(5) 0.0228(5) -0.0029(4) -0.0053(4) -0.0095(4) C6 0.0272(5) 0.0267(5) 0.0246(5) -0.0001(4) -0.0045(4) -0.0123(4) C7 0.0223(5) 0.0195(5) 0.0256(5) -0.0006(4) -0.0102(4) -0.0059(4) C8 0.0248(5) 0.0230(5) 0.0239(5) -0.0012(4) -0.0064(4) -0.0083(4) C9 0.0305(6) 0.0250(5) 0.0310(6) -0.0020(4) -0.0080(5) -0.0142(5) C10 0.0295(6) 0.0241(5) 0.0277(6) -0.0046(4) -0.0088(5) -0.0103(4) C11 0.0217(5) 0.0227(5) 0.0234(5) -0.0009(4) -0.0082(4) -0.0060(4) C12 0.0224(5) 0.0208(5) 0.0252(5) -0.0002(4) -0.0092(4) -0.0075(4) C13 0.0278(5) 0.0273(5) 0.0249(5) -0.0022(4) -0.0054(4) -0.0145(4) C14 0.0212(5) 0.0216(5) 0.0240(5) -0.0008(4) -0.0077(4) -0.0068(4) C15 0.0244(5) 0.0219(5) 0.0208(5) -0.0009(4) -0.0070(4) -0.0074(4) C16 0.0183(5) 0.0239(5) 0.0239(5) -0.0025(4) -0.0063(4) -0.0069(4) C17 0.0232(5) 0.0266(5) 0.0244(5) -0.0004(4) -0.0067(4) -0.0115(4) C18 0.0243(5) 0.0251(5) 0.0327(6) -0.0032(4) -0.0081(4) -0.0119(4) C19 0.0215(5) 0.0309(6) 0.0289(6) -0.0092(4) -0.0074(4) -0.0083(4) C20 0.0258(5) 0.0315(6) 0.0232(5) -0.0017(4) -0.0082(4) -0.0074(4) C21 0.0266(5) 0.0234(5) 0.0262(5) -0.0001(4) -0.0087(4) -0.0072(4) C22 0.0229(5) 0.0263(5) 0.0252(5) -0.0043(4) -0.0092(4) -0.0087(4) C23 0.0230(5) 0.0196(5) 0.0242(5) 0.0007(4) -0.0098(4) -0.0070(4) C24 0.0266(5) 0.0267(5) 0.0239(5) 0.0014(4) -0.0084(4) -0.0138(4) C25 0.0225(5) 0.0192(5) 0.0231(5) 0.0008(4) -0.0095(4) -0.0058(4) C26 0.0232(5) 0.0265(5) 0.0250(5) -0.0010(4) -0.0061(4) -0.0104(4) C27 0.0284(5) 0.0266(5) 0.0292(6) -0.0020(4) -0.0113(5) -0.0119(4) C28 0.0292(6) 0.0277(5) 0.0236(5) -0.0038(4) -0.0088(4) -0.0080(4) C29 0.0245(5) 0.0349(6) 0.0254(5) -0.0018(5) -0.0047(4) -0.0111(5) C30 0.0248(5) 0.0288(5) 0.0276(6) 0.0001(4) -0.0097(4) -0.0122(4) N1 0.0236(4) 0.0218(4) 0.0218(4) -0.0010(3) -0.0061(3) -0.0093(3) N2 0.0282(5) 0.0293(5) 0.0233(5) -0.0015(4) -0.0037(4) -0.0159(4) N3 0.0227(4) 0.0230(4) 0.0237(4) -0.0019(3) -0.0083(4) -0.0087(3) N4 0.0283(5) 0.0271(5) 0.0255(5) 0.0009(4) -0.0094(4) -0.0155(4) O1 0.0321(4) 0.0258(4) 0.0251(4) -0.0031(3) -0.0047(3) -0.0152(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 O1 C1 C6 124.39(10) . . ? O1 C1 C2 112.27(9) . . ? C6 C1 C2 123.34(10) . . ? C1 C2 C3 119.42(10) . . ? C1 C2 C7 105.29(9) . . ? C3 C2 C7 135.29(10) . . ? C4 C3 C2 117.78(10) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C3 C4 C5 121.65(10) . . ? C3 C4 N1 119.92(9) . . ? C5 C4 N1 118.42(9) . . ? C6 C5 C4 120.96(10) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C1 C6 C5 116.85(10) . . ? C1 C6 H6 121.6 . . ? C5 C6 H6 121.6 . . ? C12 C7 C8 119.36(9) . . ? C12 C7 C2 135.32(10) . . ? C8 C7 C2 105.32(9) . . ? C9 C8 O1 124.27(10) . . ? C9 C8 C7 123.63(10) . . ? O1 C8 C7 112.10(9) . . ? C8 C9 C10 116.70(10) . . ? C8 C9 H9 121.7 . . ? C10 C9 H9 121.7 . . ? C9 C10 C11 120.90(10) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C12 C11 C10 121.96(10) . . ? C12 C11 N3 120.45(9) . . ? C10 C11 N3 117.56(9) . . ? C11 C12 C7 117.43(10) . . ? C11 C12 H12 121.3 . . ? C7 C12 H12 121.3 . . ? N2 C13 C14 112.40(9) . . ? N2 C13 H13 123.8 . . ? C14 C13 H13 123.8 . . ? C15 C14 C13 103.80(9) . . ? C15 C14 C16 126.86(10) . . ? C13 C14 C16 129.34(10) . . ? N1 C15 C14 107.71(9) . . ? N1 C15 H15 126.1 . . ? C14 C15 H15 126.1 . . ? C17 C16 C21 118.07(10) . . ? C17 C16 C14 121.14(10) . . ? C21 C16 C14 120.78(9) . . ? C18 C17 C16 121.15(10) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C17 119.99(10) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 119.63(10) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C21 C20 C19 120.21(10) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C16 120.94(10) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? N3 C22 C23 108.06(9) . . ? N3 C22 H22 126.0 . . ? C23 C22 H22 126.0 . . ? C22 C23 C24 103.45(9) . . ? C22 C23 C25 126.89(10) . . ? C24 C23 C25 129.42(10) . . ? N4 C24 C23 112.58(9) . . ? N4 C24 H24 123.7 . . ? C23 C24 H24 123.7 . . ? C30 C25 C26 118.06(10) . . ? C30 C25 C23 121.51(9) . . ? C26 C25 C23 120.40(9) . . ? C27 C26 C25 120.88(10) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C26 C27 C28 120.39(10) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C29 C28 C27 119.37(10) . . ? C29 C28 H28 120.3 . . ? C27 C28 H28 120.3 . . ? C28 C29 C30 120.42(10) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C29 C30 C25 120.87(10) . . ? C29 C30 H30 119.6 . . ? C25 C30 H30 119.6 . . ? C15 N1 N2 111.74(8) . . ? C15 N1 C4 128.00(9) . . ? N2 N1 C4 120.23(8) . . ? C13 N2 N1 104.35(9) . . ? C22 N3 N4 111.67(9) . . ? C22 N3 C11 126.80(9) . . ? N4 N3 C11 121.01(8) . . ? C24 N4 N3 104.22(8) . . ? C1 O1 C8 105.02(8) . . ? 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 C1 O1 1.3809(12) . ? C1 C6 1.3818(15) . ? C1 C2 1.3954(15) . ? C2 C3 1.3974(14) . ? C2 C7 1.4548(14) . ? C3 C4 1.3875(15) . ? C3 H3 0.9500 . ? C4 C5 1.4018(15) . ? C4 N1 1.4262(13) . ? C5 C6 1.3841(15) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.3973(15) . ? C7 C8 1.3978(15) . ? C8 C9 1.3799(15) . ? C8 O1 1.3818(13) . ? C9 C10 1.3811(16) . ? C9 H9 0.9500 . ? C10 C11 1.4038(15) . ? C10 H10 0.9500 . ? C11 C12 1.3881(14) . ? C11 N3 1.4265(14) . ? C12 H12 0.9500 . ? C13 N2 1.3296(14) . ? C13 C14 1.4119(15) . ? C13 H13 0.9500 . ? C14 C15 1.3773(15) . ? C14 C16 1.4699(14) . ? C15 N1 1.3540(13) . ? C15 H15 0.9500 . ? C16 C17 1.3972(15) . ? C16 C21 1.4005(15) . ? C17 C18 1.3907(15) . ? C17 H17 0.9500 . ? C18 C19 1.3900(16) . ? C18 H18 0.9500 . ? C19 C20 1.3898(16) . ? C19 H19 0.9500 . ? C20 C21 1.3887(15) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 N3 1.3538(13) . ? C22 C23 1.3751(15) . ? C22 H22 0.9500 . ? C23 C24 1.4126(14) . ? C23 C25 1.4707(14) . ? C24 N4 1.3318(14) . ? C24 H24 0.9500 . ? C25 C30 1.3943(15) . ? C25 C26 1.4026(15) . ? C26 C27 1.3847(15) . ? C26 H26 0.9500 . ? C27 C28 1.3874(16) . ? C27 H27 0.9500 . ? C28 C29 1.3852(16) . ? C28 H28 0.9500 . ? C29 C30 1.3897(15) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? N1 N2 1.3639(12) . ? N3 N4 1.3612(12) . ? 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 C1 C2 C3 -179.67(9) . . . . ? C6 C1 C2 C3 0.62(16) . . . . ? O1 C1 C2 C7 0.84(12) . . . . ? C6 C1 C2 C7 -178.87(10) . . . . ? C1 C2 C3 C4 -1.19(15) . . . . ? C7 C2 C3 C4 178.11(11) . . . . ? C2 C3 C4 C5 1.17(15) . . . . ? C2 C3 C4 N1 -178.06(9) . . . . ? C3 C4 C5 C6 -0.55(16) . . . . ? N1 C4 C5 C6 178.69(10) . . . . ? O1 C1 C6 C5 -179.65(10) . . . . ? C2 C1 C6 C5 0.03(16) . . . . ? C4 C5 C6 C1 -0.07(16) . . . . ? C1 C2 C7 C12 178.48(11) . . . . ? C3 C2 C7 C12 -0.9(2) . . . . ? C1 C2 C7 C8 -0.55(11) . . . . ? C3 C2 C7 C8 -179.91(12) . . . . ? C12 C7 C8 C9 1.03(16) . . . . ? C2 C7 C8 C9 -179.76(10) . . . . ? C12 C7 C8 O1 -179.12(9) . . . . ? C2 C7 C8 O1 0.09(12) . . . . ? O1 C8 C9 C10 -179.95(10) . . . . ? C7 C8 C9 C10 -0.12(17) . . . . ? C8 C9 C10 C11 -1.03(16) . . . . ? C9 C10 C11 C12 1.31(17) . . . . ? C9 C10 C11 N3 179.45(10) . . . . ? C10 C11 C12 C7 -0.37(15) . . . . ? N3 C11 C12 C7 -178.46(9) . . . . ? C8 C7 C12 C11 -0.75(15) . . . . ? C2 C7 C12 C11 -179.67(11) . . . . ? N2 C13 C14 C15 -0.23(13) . . . . ? N2 C13 C14 C16 -179.20(10) . . . . ? C13 C14 C15 N1 0.00(11) . . . . ? C16 C14 C15 N1 179.01(9) . . . . ? C15 C14 C16 C17 -155.46(11) . . . . ? C13 C14 C16 C17 23.30(17) . . . . ? C15 C14 C16 C21 23.63(16) . . . . ? C13 C14 C16 C21 -157.61(11) . . . . ? C21 C16 C17 C18 -0.74(15) . . . . ? C14 C16 C17 C18 178.38(10) . . . . ? C16 C17 C18 C19 0.29(16) . . . . ? C17 C18 C19 C20 0.62(16) . . . . ? C18 C19 C20 C21 -1.06(16) . . . . ? C19 C20 C21 C16 0.60(16) . . . . ? C17 C16 C21 C20 0.30(16) . . . . ? C14 C16 C21 C20 -178.82(9) . . . . ? N3 C22 C23 C24 -0.85(12) . . . . ? N3 C22 C23 C25 173.97(9) . . . . ? C22 C23 C24 N4 0.83(12) . . . . ? C25 C23 C24 N4 -173.81(10) . . . . ? C22 C23 C25 C30 177.28(10) . . . . ? C24 C23 C25 C30 -9.24(17) . . . . ? C22 C23 C25 C26 -4.52(16) . . . . ? C24 C23 C25 C26 168.96(11) . . . . ? C30 C25 C26 C27 -0.18(16) . . . . ? C23 C25 C26 C27 -178.44(10) . . . . ? C25 C26 C27 C28 1.17(16) . . . . ? C26 C27 C28 C29 -1.03(17) . . . . ? C27 C28 C29 C30 -0.08(17) . . . . ? C28 C29 C30 C25 1.08(17) . . . . ? C26 C25 C30 C29 -0.94(16) . . . . ? C23 C25 C30 C29 177.30(10) . . . . ? C14 C15 N1 N2 0.22(12) . . . . ? C14 C15 N1 C4 -177.57(10) . . . . ? C3 C4 N1 C15 -169.92(10) . . . . ? C5 C4 N1 C15 10.82(16) . . . . ? C3 C4 N1 N2 12.46(14) . . . . ? C5 C4 N1 N2 -166.80(9) . . . . ? C14 C13 N2 N1 0.35(12) . . . . ? C15 N1 N2 C13 -0.35(12) . . . . ? C4 N1 N2 C13 177.63(9) . . . . ? C23 C22 N3 N4 0.65(12) . . . . ? C23 C22 N3 C11 -171.18(9) . . . . ? C12 C11 N3 C22 -155.77(10) . . . . ? C10 C11 N3 C22 26.05(15) . . . . ? C12 C11 N3 N4 33.09(14) . . . . ? C10 C11 N3 N4 -145.09(10) . . . . ? C23 C24 N4 N3 -0.45(12) . . . . ? C22 N3 N4 C24 -0.12(11) . . . . ? C11 N3 N4 C24 172.25(9) . . . . ? C6 C1 O1 C8 178.93(10) . . . . ? C2 C1 O1 C8 -0.79(12) . . . . ? C9 C8 O1 C1 -179.75(10) . . . . ? C7 C8 O1 C1 0.41(11) . . . . ?