#------------------------------------------------------------------------------ #$Date: 2021-11-04 03:32:32 +0200 (Thu, 04 Nov 2021) $ #$Revision: 270288 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061041.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_7061041 loop_ _publ_author_name 'Bhuin, Shouvik' 'Bhattacharya, Suman' 'Chakravarty, Manab' _publ_section_title ; Acceptor--donor--acceptor-linked triphenylamine and phenothiazine motifs as cousin molecules: the methyl effect on stimuli-responsiveness, crystallochromism, and dual-state emission ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ04190H _journal_year 2021 _chemical_formula_moiety 'C26 H18 N4' _chemical_formula_sum 'C26 H18 N4' _chemical_formula_weight 386.44 _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 mixed _atom_sites_solution_primary direct _audit_creation_date 2020-06-01 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-02-12 deposited with the CCDC. 2021-10-22 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.9384(18) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 17.0172(3) _cell_length_b 14.7978(3) _cell_length_c 8.29705(16) _cell_measurement_reflns_used 4711 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 78.4190 _cell_measurement_theta_min 5.2470 _cell_volume 2063.97(7) _computing_cell_refinement 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _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 293(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.973 _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 13.00 89.00 0.50 12.00 -- 0.00 57.00 60.00 152 2 \w -29.00 26.00 0.50 12.00 -- 0.00 77.00 120.00 110 3 \w -88.00 -8.00 0.50 12.00 -- 0.00 -37.00 -60.00 160 4 \w 104.00 138.00 0.50 48.00 -- 107.20 -77.00-180.00 68 5 \w 50.00 137.00 0.50 48.00 -- 107.20 -82.00-120.00 174 6 \w 28.00 73.00 0.50 48.00 -- 107.20 -77.00-180.00 90 7 \w 58.00 124.00 0.50 48.00 -- 107.20 -30.00 90.00 132 8 \w 19.00 44.00 0.50 48.00 -- 107.20 -30.00 90.00 50 9 \w 21.00 53.00 0.50 48.00 -- 107.20 -82.00 -60.00 64 10 \w 80.00 114.00 0.50 48.00 -- 107.20 -82.00 -60.00 68 11 \w 42.00 132.00 0.50 48.00 -- 107.20 -61.00 0.00 180 12 \w 61.00 115.00 0.50 48.00 -- 107.20 -82.00 0.00 108 13 \w 91.00 197.00 0.50 48.00 -- 107.20 45.00 120.00 212 14 \w 88.00 186.00 0.50 48.00 -- 107.20 45.00 150.00 196 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa dual home/near' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0326279000 _diffrn_orient_matrix_UB_12 0.0963339000 _diffrn_orient_matrix_UB_13 0.0347406000 _diffrn_orient_matrix_UB_21 -0.0855989000 _diffrn_orient_matrix_UB_22 0.0372864000 _diffrn_orient_matrix_UB_23 -0.0262733000 _diffrn_orient_matrix_UB_31 -0.0038008000 _diffrn_orient_matrix_UB_32 -0.0129690000 _diffrn_orient_matrix_UB_33 0.1827699000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_unetI/netI 0.0410 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.973 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 12949 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.973 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.613 _diffrn_reflns_theta_min 3.980 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.589 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59328 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.244 _exptl_crystal_description needle _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.737 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.043 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 4377 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0841 _refine_ls_R_factor_gt 0.0670 _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^)+(0.0985P)^2^+0.6480P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1902 _refine_ls_wR_factor_ref 0.2056 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3233 _reflns_number_total 4377 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj04190h2.cif _cod_data_source_block exp_400-sbamact _cod_original_cell_volume 2063.96(7) _cod_database_code 7061041 _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. ; _reflns_odcompleteness_completeness 99.65 _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 N(H,H) groups 2.a Rotating group: N2(H2A,H2B) 2.b Aromatic/amide H refined with riding coordinates: C10(H10), C11(H11), C14(H14), C13(H13), C3(H3), C2(H2), C22(H22), C23(H23), C18(H18), C16(H16), C26(H26), C17(H17), C19(H19), C20(H20), C25(H25), C24(H24) ; _shelx_res_file ; TITL exp_400-SB AMACT in P21/c #14 exp_400-sbamact.res created by SHELXL-2018/3 at 23:22:31 on 01-Jun-2020 REM reset to P21/c #14 CELL 1.54184 17.017186 14.797765 8.297051 90 98.9384 90 ZERR 4 0.000337 0.000321 0.000159 0 0.0018 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N UNIT 104 72 16 L.S. 4 0 0 PLAN 1 BOND fmap 2 53 acta REM REM REM WGHT 0.098500 0.648000 FVAR 1.43758 C4 1 0.501130 0.292525 -0.159644 11.00000 0.04211 0.06012 = 0.05486 -0.00779 0.01514 -0.00242 C12 1 0.728866 0.383762 0.086348 11.00000 0.04374 0.05949 = 0.05923 -0.00178 0.00908 -0.00684 C10 1 0.585658 0.397215 0.031113 11.00000 0.04751 0.05169 = 0.05407 -0.00199 0.01090 0.00454 AFIX 43 H10 2 0.539613 0.426559 0.049930 11.00000 -1.20000 AFIX 0 C5 1 0.482992 0.200097 -0.164844 11.00000 0.04375 0.06110 = 0.05884 -0.00823 0.01644 -0.00493 C11 1 0.658200 0.426880 0.110835 11.00000 0.05113 0.05231 = 0.05581 -0.00512 0.00791 -0.00037 AFIX 43 H11 2 0.660340 0.475914 0.181495 11.00000 -1.20000 AFIX 0 C9 1 0.579395 0.324908 -0.076276 11.00000 0.04154 0.05322 = 0.05466 -0.00272 0.01161 -0.00279 N4 3 0.802489 0.410241 0.171344 11.00000 0.04327 0.08418 = 0.06960 -0.01537 0.00773 -0.00938 C8 1 0.534703 0.134639 -0.076542 11.00000 0.05176 0.06028 = 0.07147 -0.00793 0.02044 -0.00862 C14 1 0.649939 0.284974 -0.106506 11.00000 0.04413 0.06143 = 0.07406 -0.02002 0.01726 -0.00489 AFIX 43 H14 2 0.647661 0.237950 -0.181452 11.00000 -1.20000 AFIX 0 C6 1 0.410723 0.167043 -0.252892 11.00000 0.05038 0.07531 = 0.06422 -0.01707 0.02029 -0.01680 C13 1 0.722794 0.313695 -0.027783 11.00000 0.04141 0.06751 = 0.08258 -0.01915 0.01685 -0.00247 AFIX 43 H13 2 0.768806 0.285986 -0.050942 11.00000 -1.20000 AFIX 0 N3 3 0.571127 0.077580 -0.007321 11.00000 0.06329 0.06816 = 0.10454 0.00298 0.01945 -0.00181 C3 1 0.444844 0.352560 -0.237642 11.00000 0.04967 0.06844 = 0.06648 -0.00275 0.00962 0.00279 AFIX 43 H3 2 0.455201 0.414283 -0.232051 11.00000 -1.20000 AFIX 0 C1 1 0.357139 0.230548 -0.333649 11.00000 0.04296 0.09685 = 0.06151 -0.00901 0.01006 -0.00884 C15 1 0.874308 0.386356 0.111842 11.00000 0.04292 0.07538 = 0.06864 -0.00761 0.00745 -0.01000 C2 1 0.373824 0.321876 -0.323241 11.00000 0.04646 0.09261 = 0.06582 -0.00173 0.00768 0.00360 AFIX 43 H2 2 0.336855 0.363091 -0.374395 11.00000 -1.20000 AFIX 0 C21 1 0.809962 0.462611 0.316917 11.00000 0.05386 0.07189 = 0.06119 -0.00361 0.00551 -0.01340 N2 3 0.395820 0.075989 -0.262651 11.00000 0.07247 0.08417 = 0.09803 -0.01415 0.01079 -0.02766 AFIX 7 H2A 2 0.414640 0.050978 -0.171182 11.00000 -1.20000 H2B 2 0.345249 0.067419 -0.282939 11.00000 -1.20000 AFIX 0 C7 1 0.284196 0.197718 -0.422842 11.00000 0.05451 0.13602 = 0.07857 -0.01474 0.00679 -0.02100 C22 1 0.769115 0.440404 0.443113 11.00000 0.05859 0.09048 = 0.06433 0.00141 0.00631 -0.01555 AFIX 43 H22 2 0.735632 0.390376 0.433253 11.00000 -1.20000 AFIX 0 C23 1 0.777550 0.491465 0.582525 11.00000 0.07654 0.14204 = 0.05940 -0.00566 0.01020 -0.02344 AFIX 43 H23 2 0.749384 0.476016 0.666004 11.00000 -1.20000 AFIX 0 C18 1 1.014576 0.345517 0.000277 11.00000 0.04993 0.10542 = 0.10840 -0.02106 0.02077 -0.00798 AFIX 43 H18 2 1.061858 0.331657 -0.037337 11.00000 -1.20000 AFIX 0 C16 1 0.929841 0.332806 0.201407 11.00000 0.06846 0.10358 = 0.08267 0.01026 0.01246 0.00973 AFIX 43 H16 2 0.920412 0.309259 0.300554 11.00000 -1.20000 AFIX 0 C26 1 0.859634 0.536603 0.334974 11.00000 0.10902 0.10243 = 0.08005 -0.01918 0.03342 -0.04883 AFIX 43 H26 2 0.887038 0.553063 0.250869 11.00000 -1.20000 AFIX 0 C17 1 1.000636 0.313355 0.144563 11.00000 0.06274 0.11269 = 0.10370 -0.00164 0.00638 0.01370 AFIX 43 H17 2 1.038769 0.277671 0.207152 11.00000 -1.20000 AFIX 0 C19 1 0.958838 0.398775 -0.091041 11.00000 0.06862 0.12866 = 0.09227 0.00623 0.02992 -0.01073 AFIX 43 H19 2 0.968176 0.420966 -0.191212 11.00000 -1.20000 AFIX 0 C20 1 0.888672 0.419720 -0.034908 11.00000 0.05696 0.10591 = 0.08337 0.01222 0.01679 0.00066 AFIX 43 H20 2 0.851180 0.456487 -0.096791 11.00000 -1.20000 AFIX 0 N1 3 0.226373 0.169114 -0.492417 11.00000 0.06814 0.18195 = 0.12370 -0.02999 -0.00570 -0.03535 C25 1 0.868947 0.586430 0.477188 11.00000 0.15032 0.12471 = 0.09552 -0.03440 0.03068 -0.07420 AFIX 43 H25 2 0.904009 0.635038 0.489741 11.00000 -1.20000 AFIX 0 C24 1 0.826951 0.564912 0.600230 11.00000 0.11514 0.13768 = 0.07614 -0.03442 0.01952 -0.04115 AFIX 43 H24 2 0.831996 0.599810 0.694495 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_400-SB AMACT in P21/c #14 REM wR2 = 0.2056, GooF = S = 1.059, Restrained GooF = 1.059 for all data REM R1 = 0.0670 for 3233 Fo > 4sig(Fo) and 0.0841 for all 4377 data REM 272 parameters refined using 0 restraints END WGHT 0.0985 0.6481 REM Highest difference peak 0.737, deepest hole -0.192, 1-sigma level 0.043 Q1 1 0.3124 0.3648 -0.4058 11.00000 0.05 0.74 ; _shelx_res_checksum 19093 _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 1.736 _oxdiff_exptl_absorpt_empirical_full_min 0.425 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 C4 C 0.50113(12) 0.29252(15) -0.1596(2) 0.0516(5) Uani 1 1 d . . . . . C12 C 0.72887(12) 0.38376(15) 0.0863(3) 0.0540(5) Uani 1 1 d . . . . . C10 C 0.58566(12) 0.39722(14) 0.0311(2) 0.0508(5) Uani 1 1 d . . . . . H10 H 0.539613 0.426559 0.049930 0.061 Uiso 1 1 calc R . . . . C5 C 0.48299(12) 0.20010(15) -0.1648(3) 0.0537(5) Uani 1 1 d . . . . . C11 C 0.65820(12) 0.42688(15) 0.1108(3) 0.0531(5) Uani 1 1 d . . . . . H11 H 0.660340 0.475914 0.181495 0.064 Uiso 1 1 calc R . . . . C9 C 0.57939(11) 0.32491(14) -0.0763(2) 0.0494(5) Uani 1 1 d . . . . . N4 N 0.80249(11) 0.41024(15) 0.1713(2) 0.0658(5) Uani 1 1 d . . . . . C8 C 0.53470(14) 0.13464(17) -0.0765(3) 0.0600(6) Uani 1 1 d . . . . . C14 C 0.64994(12) 0.28497(16) -0.1065(3) 0.0590(6) Uani 1 1 d . . . . . H14 H 0.647661 0.237950 -0.181452 0.071 Uiso 1 1 calc R . . . . C6 C 0.41072(13) 0.16704(18) -0.2529(3) 0.0621(6) Uani 1 1 d . . . . . C13 C 0.72279(13) 0.31370(17) -0.0278(3) 0.0631(6) Uani 1 1 d . . . . . H13 H 0.768806 0.285986 -0.050942 0.076 Uiso 1 1 calc R . . . . N3 N 0.57113(14) 0.07758(16) -0.0073(3) 0.0780(6) Uani 1 1 d . . . . . C3 C 0.44484(13) 0.35256(17) -0.2376(3) 0.0615(6) Uani 1 1 d . . . . . H3 H 0.455201 0.414283 -0.232051 0.074 Uiso 1 1 calc R . . . . C1 C 0.35714(13) 0.2305(2) -0.3336(3) 0.0669(7) Uani 1 1 d . . . . . C15 C 0.87431(13) 0.38636(18) 0.1118(3) 0.0624(6) Uani 1 1 d . . . . . C2 C 0.37382(14) 0.3219(2) -0.3232(3) 0.0684(7) Uani 1 1 d . . . . . H2 H 0.336855 0.363091 -0.374395 0.082 Uiso 1 1 calc R . . . . C21 C 0.80996(14) 0.46261(17) 0.3169(3) 0.0627(6) Uani 1 1 d . . . . . N2 N 0.39582(15) 0.07599(17) -0.2627(3) 0.0852(7) Uani 1 1 d . . . . . H2A H 0.414640 0.050978 -0.171182 0.102 Uiso 1 1 d GR . . . . H2B H 0.345249 0.067419 -0.282939 0.102 Uiso 1 1 d GR . . . . C7 C 0.28420(16) 0.1977(3) -0.4228(4) 0.0901(9) Uani 1 1 d . . . . . C22 C 0.76912(15) 0.4404(2) 0.4431(3) 0.0715(7) Uani 1 1 d . . . . . H22 H 0.735632 0.390376 0.433253 0.086 Uiso 1 1 calc R . . . . C23 C 0.77755(18) 0.4915(3) 0.5825(3) 0.0927(10) Uani 1 1 d . . . . . H23 H 0.749384 0.476016 0.666004 0.111 Uiso 1 1 calc R . . . . C18 C 1.01458(16) 0.3455(2) 0.0003(4) 0.0870(9) Uani 1 1 d . . . . . H18 H 1.061858 0.331657 -0.037337 0.104 Uiso 1 1 calc R . . . . C16 C 0.92984(17) 0.3328(2) 0.2014(4) 0.0848(8) Uani 1 1 d . . . . . H16 H 0.920412 0.309259 0.300554 0.102 Uiso 1 1 calc R . . . . C26 C 0.8596(2) 0.5366(2) 0.3350(4) 0.0952(10) Uani 1 1 d . . . . . H26 H 0.887038 0.553063 0.250869 0.114 Uiso 1 1 calc R . . . . C17 C 1.00064(18) 0.3134(2) 0.1446(5) 0.0937(9) Uani 1 1 d . . . . . H17 H 1.038769 0.277671 0.207152 0.112 Uiso 1 1 calc R . . . . C19 C 0.95884(18) 0.3988(3) -0.0910(4) 0.0947(10) Uani 1 1 d . . . . . H19 H 0.968176 0.420966 -0.191212 0.114 Uiso 1 1 calc R . . . . C20 C 0.88867(16) 0.4197(2) -0.0349(4) 0.0815(8) Uani 1 1 d . . . . . H20 H 0.851180 0.456487 -0.096791 0.098 Uiso 1 1 calc R . . . . N1 N 0.22637(17) 0.1691(3) -0.4924(4) 0.1268(12) Uani 1 1 d . . . . . C25 C 0.8689(3) 0.5864(3) 0.4772(5) 0.1223(15) Uani 1 1 d . . . . . H25 H 0.904009 0.635038 0.489741 0.147 Uiso 1 1 calc R . . . . C24 C 0.8270(2) 0.5649(3) 0.6002(4) 0.1092(12) Uani 1 1 d . . . . . H24 H 0.831996 0.599810 0.694495 0.131 Uiso 1 1 calc R . . . . 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 C4 0.0421(10) 0.0601(12) 0.0549(11) -0.0078(9) 0.0151(8) -0.0024(9) C12 0.0437(10) 0.0595(12) 0.0592(12) -0.0018(9) 0.0091(9) -0.0068(9) C10 0.0475(10) 0.0517(11) 0.0541(11) -0.0020(9) 0.0109(8) 0.0045(8) C5 0.0438(10) 0.0611(13) 0.0588(11) -0.0082(10) 0.0164(9) -0.0049(9) C11 0.0511(11) 0.0523(11) 0.0558(11) -0.0051(9) 0.0079(9) -0.0004(9) C9 0.0415(10) 0.0532(11) 0.0547(11) -0.0027(8) 0.0116(8) -0.0028(8) N4 0.0433(10) 0.0842(14) 0.0696(12) -0.0154(10) 0.0077(8) -0.0094(9) C8 0.0518(12) 0.0603(13) 0.0715(14) -0.0079(11) 0.0204(10) -0.0086(11) C14 0.0441(11) 0.0614(13) 0.0741(13) -0.0200(11) 0.0173(9) -0.0049(9) C6 0.0504(12) 0.0753(15) 0.0642(13) -0.0171(11) 0.0203(10) -0.0168(11) C13 0.0414(10) 0.0675(14) 0.0826(15) -0.0192(12) 0.0169(10) -0.0025(10) N3 0.0633(13) 0.0682(13) 0.1045(17) 0.0030(12) 0.0194(12) -0.0018(11) C3 0.0497(12) 0.0684(14) 0.0665(13) -0.0028(11) 0.0096(10) 0.0028(10) C1 0.0430(11) 0.0968(19) 0.0615(13) -0.0090(12) 0.0101(9) -0.0088(12) C15 0.0429(11) 0.0754(15) 0.0686(13) -0.0076(11) 0.0075(9) -0.0100(10) C2 0.0465(12) 0.0926(19) 0.0658(14) -0.0017(12) 0.0077(10) 0.0036(12) C21 0.0539(12) 0.0719(15) 0.0612(12) -0.0036(11) 0.0055(10) -0.0134(11) N2 0.0725(15) 0.0842(16) 0.0980(17) -0.0141(13) 0.0108(12) -0.0277(12) C7 0.0545(14) 0.136(3) 0.0786(17) -0.0147(18) 0.0068(13) -0.0210(16) C22 0.0586(14) 0.0905(19) 0.0643(14) 0.0014(13) 0.0063(11) -0.0156(13) C23 0.0765(18) 0.142(3) 0.0594(15) -0.0057(16) 0.0102(13) -0.0234(19) C18 0.0499(14) 0.105(2) 0.108(2) -0.0211(19) 0.0208(14) -0.0080(14) C16 0.0685(17) 0.104(2) 0.0827(18) 0.0103(16) 0.0125(14) 0.0097(15) C26 0.109(2) 0.102(2) 0.0800(18) -0.0192(16) 0.0334(17) -0.0488(19) C17 0.0627(16) 0.113(3) 0.104(2) -0.0016(19) 0.0064(15) 0.0137(16) C19 0.0686(18) 0.129(3) 0.092(2) 0.0062(19) 0.0299(16) -0.0107(18) C20 0.0570(14) 0.106(2) 0.0834(18) 0.0122(16) 0.0168(13) 0.0007(14) N1 0.0681(17) 0.182(4) 0.124(2) -0.030(2) -0.0057(16) -0.035(2) C25 0.150(4) 0.125(3) 0.096(2) -0.034(2) 0.031(2) -0.074(3) C24 0.115(3) 0.138(3) 0.0761(19) -0.034(2) 0.0195(18) -0.041(2) 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' 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 C5 C4 C9 120.51(19) . . ? C3 C4 C5 118.5(2) . . ? C3 C4 C9 121.0(2) . . ? N4 C12 C11 121.4(2) . . ? N4 C12 C13 121.1(2) . . ? C13 C12 C11 117.43(19) . . ? C11 C10 C9 121.87(19) . . ? C4 C5 C8 121.99(19) . . ? C4 C5 C6 121.5(2) . . ? C6 C5 C8 116.5(2) . . ? C10 C11 C12 120.6(2) . . ? C10 C9 C4 121.57(18) . . ? C10 C9 C14 117.40(18) . . ? C14 C9 C4 121.01(19) . . ? C12 N4 C15 120.27(19) . . ? C12 N4 C21 122.44(19) . . ? C21 N4 C15 117.28(18) . . ? N3 C8 C5 174.6(2) . . ? C13 C14 C9 121.4(2) . . ? C1 C6 C5 117.5(2) . . ? N2 C6 C5 120.5(2) . . ? N2 C6 C1 121.9(2) . . ? C14 C13 C12 121.2(2) . . ? C2 C3 C4 120.9(2) . . ? C6 C1 C7 117.8(3) . . ? C2 C1 C6 120.9(2) . . ? C2 C1 C7 121.3(3) . . ? C16 C15 N4 120.8(2) . . ? C16 C15 C20 119.3(2) . . ? C20 C15 N4 119.8(2) . . ? C3 C2 C1 120.6(2) . . ? C22 C21 N4 121.6(2) . . ? C26 C21 N4 119.8(2) . . ? C26 C21 C22 118.6(2) . . ? N1 C7 C1 178.1(4) . . ? C23 C22 C21 120.6(3) . . ? C24 C23 C22 120.7(3) . . ? C17 C18 C19 119.6(3) . . ? C15 C16 C17 120.0(3) . . ? C21 C26 C25 120.3(3) . . ? C18 C17 C16 120.8(3) . . ? C18 C19 C20 120.2(3) . . ? C15 C20 C19 120.1(3) . . ? C24 C25 C26 120.6(3) . . ? C23 C24 C25 119.2(3) . . ? 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 C4 C5 1.401(3) . ? C4 C9 1.482(3) . ? C4 C3 1.390(3) . ? C12 C11 1.404(3) . ? C12 N4 1.395(3) . ? C12 C13 1.397(3) . ? C10 C11 1.379(3) . ? C10 C9 1.386(3) . ? C5 C8 1.431(3) . ? C5 C6 1.416(3) . ? C9 C14 1.395(3) . ? N4 C15 1.432(3) . ? N4 C21 1.424(3) . ? C8 N3 1.147(3) . ? C14 C13 1.376(3) . ? C6 C1 1.405(4) . ? C6 N2 1.371(3) . ? C3 C2 1.380(3) . ? C1 C2 1.381(4) . ? C1 C7 1.428(3) . ? C15 C16 1.362(4) . ? C15 C20 1.371(4) . ? C21 C22 1.383(3) . ? C21 C26 1.377(4) . ? C7 N1 1.142(4) . ? C22 C23 1.370(4) . ? C23 C24 1.368(5) . ? C18 C17 1.343(5) . ? C18 C19 1.368(5) . ? C16 C17 1.390(4) . ? C26 C25 1.379(5) . ? C19 C20 1.383(4) . ? C25 C24 1.372(5) . ?