#------------------------------------------------------------------------------ #$Date: 2020-04-22 23:50:13 +0300 (Wed, 22 Apr 2020) $ #$Revision: 251054 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557859.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_1557859 loop_ _publ_author_name 'Yuan, Jie' 'Wang, Yongrong' 'Li, Ling' 'Wang, Shuang' 'Tang, Xingxing' 'Wang, Honglei' 'Li, Mingguang' 'Zheng, Chao' 'Chen, Runfeng' _publ_section_title ; Activating Intersystem Crossing and Aggregation Coupling by CN-Substitution for Efficient Organic Ultralong Room Temperature Phosphorescence ; _journal_name_full 'The Journal of Physical Chemistry C' _journal_paper_doi 10.1021/acs.jpcc.0c01762 _journal_year 2020 _chemical_formula_moiety 'C8 H4 N2' _chemical_formula_sum 'C8 H4 N2' _chemical_formula_weight 128.13 _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 _atom_sites_solution_primary dual _audit_creation_date 2018-05-24 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324) ; _cell_angle_alpha 89.88(4) _cell_angle_beta 85.59(3) _cell_angle_gamma 89.86(3) _cell_formula_units_Z 4 _cell_length_a 3.909(4) _cell_length_b 11.970(13) _cell_length_c 14.614(14) _cell_measurement_reflns_used 150 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 0.925 _cell_measurement_theta_min 0.911 _cell_volume 681.8(12) _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 297.2 _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_unetI/netI 0.0568 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 5958 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.071 _diffrn_reflns_theta_min 1.398 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _exptl_absorpt_coefficient_mu 0.078 _exptl_crystal_density_diffrn 1.248 _exptl_crystal_description block _exptl_crystal_F_000 264 _exptl_crystal_size_max 1 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.6 _refine_diff_density_max 0.150 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.053 _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 181 _refine_ls_number_reflns 3257 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.1167 _refine_ls_R_factor_gt 0.0568 _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^)+(0.0618P)^2^+0.0268P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1177 _refine_ls_wR_factor_ref 0.1433 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1806 _reflns_number_total 3257 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jp0c01762_si_002.cif _cod_data_source_block 1 _cod_original_cell_volume 681.9(12) _cod_database_code 1557859 _shelx_shelxl_version_number 2014/7 _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 0.926 _shelx_estimated_absorpt_t_min 0.744 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C006(H006), C008(H008) ; _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1_a.res in P-1 REM Old TITL 1 in P-1 REM SHELXT solution in P-1 REM R1 0.146, Rweak 0.009, Alpha 0.029, Orientation as input REM Formula found by SHELXT: C16 N4 CELL 0.71073 3.9094 11.9701 14.6142 89.876 85.592 89.855 ZERR 4 0.0039 0.0128 0.0135 0.037 0.026 0.026 LATT 1 SFAC C H N UNIT 32 16 8 L.S. 10 PLAN 20 SIZE 1 1 4 TEMP 24.05 BOND $H list 4 fmap 2 ACTA REM REM REM WGHT 0.061800 0.026800 FVAR 1.47066 C00B 1 0.848179 0.033039 0.378969 11.00000 0.04781 0.04847 = 0.05481 -0.00418 -0.00611 -0.00181 C00C 1 0.848413 0.467278 -0.120928 11.00000 0.04820 0.04882 = 0.05548 0.00702 -0.00559 0.00083 C00D 1 0.376660 0.348893 0.358566 11.00000 0.05142 0.04504 = 0.06171 0.00853 -0.00630 0.00037 AFIX 43 H00D 2 0.272801 0.418430 0.353810 11.00000 -1.20000 AFIX 0 C00E 1 0.376442 0.150813 -0.141111 11.00000 0.05157 0.04655 = 0.06190 -0.00726 -0.00505 -0.00252 AFIX 43 H00E 2 0.273400 0.081301 -0.145599 11.00000 -1.20000 AFIX 0 C00F 1 0.289640 0.138690 0.026953 11.00000 0.05246 0.04847 = 0.05861 0.00152 -0.00114 -0.00239 C00G 1 0.290469 0.361169 0.526856 11.00000 0.05104 0.04768 = 0.05801 -0.00166 0.00016 0.00016 C00H 1 0.646535 0.187670 0.286671 11.00000 0.05496 0.06062 = 0.04723 -0.00485 -0.00006 -0.00067 AFIX 43 H00H 2 0.723307 0.149295 0.233727 11.00000 -1.20000 AFIX 0 C00I 1 0.647216 0.312176 -0.213376 11.00000 0.05495 0.06148 = 0.04632 0.00610 0.00049 -0.00269 AFIX 43 H00I 2 0.724741 0.350444 -0.266385 11.00000 -1.20000 AFIX 0 C00J 1 0.491369 0.208826 -0.219617 11.00000 0.06977 0.06566 = 0.04845 -0.01115 -0.00600 -0.00410 AFIX 43 H00J 2 0.463756 0.178189 -0.277002 11.00000 -1.20000 AFIX 0 C00K 1 0.491342 0.291051 0.280318 11.00000 0.06825 0.06372 = 0.04806 0.01106 -0.00637 0.00273 AFIX 43 H00K 2 0.463879 0.321939 0.222890 11.00000 -1.20000 AFIX 0 C002 1 0.687508 0.141192 0.372638 11.00000 0.03720 0.04223 = 0.04911 -0.00105 -0.00421 -0.00479 C004 1 0.687400 0.358552 -0.127539 11.00000 0.03668 0.04079 = 0.05042 0.00177 -0.00397 0.00363 C005 1 0.417478 0.302446 0.444714 11.00000 0.03692 0.04183 = 0.05011 -0.00024 -0.00173 -0.00413 C006 1 0.573767 0.198562 0.452263 11.00000 0.04024 0.04432 = 0.04523 0.00293 -0.00501 -0.00619 AFIX 43 H006 2 0.602006 0.167785 0.509688 11.00000 -1.20000 AFIX 0 C007 1 0.416581 0.197505 -0.055441 11.00000 0.03787 0.04320 = 0.04906 0.00018 -0.00007 0.00336 C008 1 0.574212 0.301695 -0.047837 11.00000 0.04124 0.04306 = 0.04533 -0.00354 -0.00411 0.00366 AFIX 43 H008 2 0.602679 0.332314 0.009507 11.00000 -1.20000 AFIX 0 N00A 3 0.183691 0.092884 0.092175 11.00000 0.08501 0.06783 = 0.06710 0.01074 0.00820 -0.01147 N001 3 0.974223 -0.053393 0.384244 11.00000 0.07415 0.05730 = 0.07554 -0.00660 -0.00926 0.00790 N003 3 0.975169 0.553463 -0.116004 11.00000 0.07430 0.05475 = 0.07704 0.00875 -0.01044 -0.01084 N009 3 0.184283 0.406991 0.592223 11.00000 0.08545 0.06858 = 0.06795 -0.00905 0.00670 0.00962 HKLF 4 REM 1_a.res in P-1 REM R1 = 0.0568 for 1806 Fo > 4sig(Fo) and 0.1167 for all 3257 data REM 181 parameters refined using 0 restraints END WGHT 0.0618 0.0268 REM Highest difference peak 0.150, deepest hole -0.244, 1-sigma level 0.053 Q1 1 0.6892 0.3883 0.5528 11.00000 0.05 0.15 Q2 1 1.0330 0.3273 -0.0266 11.00000 0.05 0.14 Q3 1 0.2582 0.1808 -0.2838 11.00000 0.05 0.14 Q4 1 0.0008 0.2231 -0.0836 11.00000 0.05 0.14 Q5 1 0.5942 0.1202 0.0799 11.00000 0.05 0.14 Q6 1 0.0688 0.2681 0.4179 11.00000 0.05 0.14 Q7 1 0.1735 0.2022 0.1749 11.00000 0.05 0.13 Q8 1 0.0170 0.2593 0.1154 11.00000 0.05 0.13 Q9 1 0.7402 0.2330 0.0931 11.00000 0.05 0.13 Q10 1 0.5762 0.4199 0.6006 11.00000 0.05 0.13 Q11 1 0.5577 0.5794 -0.0968 11.00000 0.05 0.13 Q12 1 0.3959 0.0377 0.2044 11.00000 0.05 0.13 Q13 1 -0.1747 0.3045 0.5588 11.00000 0.05 0.13 Q14 1 0.5551 0.0415 0.0725 11.00000 0.05 0.13 Q15 1 0.9721 0.2364 -0.1009 11.00000 0.05 0.13 Q16 1 0.2241 0.3217 0.2095 11.00000 0.05 0.13 Q17 1 0.1553 0.1975 -0.3474 11.00000 0.05 0.13 Q18 1 -0.2040 0.1758 0.0263 11.00000 0.05 0.12 Q19 1 -0.2239 0.0837 0.0573 11.00000 0.05 0.12 Q20 1 0.1289 0.2823 0.1594 11.00000 0.05 0.12 ; _shelx_res_checksum 71914 _shelx_hkl_file ; 1 1 0 79.99 4.10 -1 -1 0 75.39 3.70 -2 -2 0 183.38 7.50 -2 -2 0 180.68 8.60 -3 -3 0 5.80 3.30 -3 -3 0 1.20 2.50 -4 -4 0 -9.20 3.80 -4 -5 0 18.50 4.60 -3 -4 0 221.38 9.70 -2 -3 0 2.40 1.50 -1 -2 0 9999.00 288.07 1 2 0 9682.23 288.07 1 2 0 9499.95 288.57 0 -1 0 -0.10 0.20 0 -1 0 0.90 0.30 0 1 0 0.10 0.20 1 0 0 4507.95 134.39 -1 0 0 4501.15 134.29 2 1 0 58.89 4.60 -3 -2 0 31.00 4.70 -3 -2 0 33.00 4.70 -4 -3 0 -2.50 3.80 -4 -6 0 29.20 4.80 -3 -5 0 5.10 2.50 -2 -4 0 846.02 27.10 -1 -3 0 732.13 22.70 0 -2 0 2220.58 65.99 0 2 0 2222.68 65.99 1 -1 0 74.49 3.80 -1 1 0 81.19 3.60 -1 1 0 72.59 3.50 2 0 0 1.00 2.20 3 1 0 6.10 4.00 -4 -2 0 -4.80 4.90 -4 -2 0 3.20 4.00 -5 -3 0 2.80 7.20 -5 -3 0 1.20 8.90 -4 -7 0 0.80 4.50 -3 -6 0 111.59 6.50 -2 -5 0 0.40 1.70 -1 -4 0 138.39 5.40 0 -3 0 1.50 0.60 0 3 0 1.00 0.50 1 -2 0 9131.39 277.37 -1 2 0 9640.34 277.17 -1 2 0 9449.65 277.17 -1 2 0 9199.48 277.17 2 -1 0 61.39 4.60 -2 1 0 60.19 4.30 3 0 0 83.99 8.10 -4 -1 0 9.00 5.30 -4 -1 0 7.20 4.00 -5 -2 0 -10.60 6.90 -5 -2 0 2.40 6.90 -5 -2 0 4.90 8.40 -4 -8 0 4.60 4.50 -3 -7 0 -3.30 2.50 -2 -6 0 5.20 2.20 -1 -5 0 23.20 2.10 0 -4 0 1611.54 48.40 1 -3 0 708.13 23.00 -1 3 0 747.13 22.90 2 -2 0 171.28 7.80 -2 2 0 167.58 7.10 3 -1 0 -2.30 3.60 -3 1 0 2.60 3.00 4 0 0 42.40 6.10 -4 0 0 38.30 6.70 -5 -1 0 14.40 7.60 -5 -1 0 8.00 6.50 -5 -1 0 11.80 8.30 -4 -9 0 -1.80 7.40 -4 -9 0 0.20 5.00 -3 -8 0 3.90 2.80 -2 -7 0 34.90 3.50 -1 -6 0 1176.98 36.30 0 -5 0 0.30 0.80 1 -4 0 129.39 5.50 -1 4 0 134.99 5.50 2 -3 0 1.70 2.20 -2 3 0 1.50 1.80 3 -2 0 30.20 4.30 -3 2 0 30.50 3.70 4 -1 0 13.90 5.50 -4 1 0 11.60 5.10 -5 0 0 3.10 9.80 -5 0 0 -3.10 5.90 -5 0 0 -14.10 7.50 -5 0 0 6.80 7.60 -4 -10 0 -13.30 8.00 -3 -9 0 1.20 3.00 -2 -8 0 297.27 11.20 -1 -7 0 352.86 12.10 0 -6 0 1051.49 32.40 0 -6 0 1048.10 32.70 1 -5 0 20.00 2.50 -1 5 0 22.70 2.40 2 -4 0 807.62 27.20 -2 4 0 823.32 26.30 3 -3 0 1.90 3.20 -3 3 0 -1.40 2.50 4 -2 0 8.10 5.50 -4 2 0 10.30 4.40 5 -1 0 3.70 11.30 -5 1 0 -0.30 5.80 -5 1 0 2.10 7.80 -3 -10 0 76.19 6.30 -2 -9 0 135.29 6.40 -1 -8 0 65.09 3.90 0 -7 0 -0.80 1.80 0 -7 0 0.80 1.20 1 -6 0 1186.68 37.00 -1 6 0 1166.08 36.80 2 -5 0 6.50 2.90 -2 5 0 3.90 1.90 3 -4 0 179.18 10.10 -3 4 0 200.18 8.90 4 -3 0 -0.10 5.40 -4 3 0 -3.00 4.10 -4 3 0 -7.20 4.60 5 -2 0 3.00 11.50 -5 2 0 1.60 5.70 -3 -11 0 3.00 3.70 -3 -11 0 6.80 5.80 -2 -10 0 46.10 4.40 -1 -9 0 20.10 2.70 0 -8 0 540.05 18.40 0 -8 0 574.94 19.00 1 -7 0 369.26 13.50 -1 7 0 369.36 13.30 2 -6 0 4.90 2.20 -2 6 0 11.20 2.40 3 -5 0 -3.00 3.40 -3 5 0 -1.70 2.60 -3 5 0 1.00 2.80 4 -4 0 5.90 5.70 -4 4 0 4.90 3.60 -4 4 0 -0.40 6.10 5 -3 0 5.70 11.30 -5 3 0 -0.10 5.40 -3 -12 0 3.40 4.30 -3 -12 0 -7.10 6.70 -2 -11 0 4.30 4.70 -2 -11 0 3.70 2.60 -1 -10 0 162.18 9.10 -1 -10 0 158.78 7.10 0 -9 0 -3.50 2.40 0 -9 0 -2.50 1.40 1 -8 0 65.79 4.20 -1 8 0 56.79 4.40 2 -7 0 28.90 3.50 -2 7 0 32.10 4.00 3 -6 0 104.29 8.10 -3 6 0 95.99 7.60 4 -5 0 15.20 6.30 -4 5 0 10.60 3.80 -2 -12 0 19.40 5.60 -2 -12 0 36.00 5.40 -1 -11 0 23.40 5.50 -1 -11 0 28.90 3.80 0 -10 0 0.10 2.90 0 -10 0 1.60 1.80 1 -9 0 17.80 2.50 2 -8 0 274.07 11.60 -2 8 0 266.47 11.70 3 -7 0 -6.20 3.80 -3 7 0 -1.50 3.10 4 -6 0 28.10 7.10 -4 6 0 24.40 4.20 -2 -13 0 2.50 6.30 -2 -13 0 2.00 3.80 -1 -12 0 11.50 5.90 -1 -12 0 6.30 2.70 0 -11 0 -1.50 2.10 0 -11 0 2.90 3.40 1 -10 0 162.48 7.90 2 -9 0 144.79 8.40 -2 9 0 144.39 8.00 3 -8 0 -0.40 4.30 -3 8 0 8.60 3.30 4 -7 0 6.60 7.20 -4 7 0 8.20 4.10 -2 -14 0 -9.70 4.20 -2 -14 0 6.70 7.60 -1 -13 0 1.80 3.20 -1 -13 0 7.40 5.50 0 -12 0 170.38 8.50 0 -12 0 167.78 9.30 1 -11 0 23.10 3.40 2 -10 0 53.29 6.70 -2 10 0 48.80 5.40 3 -9 0 9.40 4.80 -3 9 0 4.70 3.40 4 -8 0 7.90 8.60 -4 8 0 5.00 4.40 -1 -14 0 29.80 5.40 -1 -14 0 33.20 7.20 0 -13 0 6.30 3.60 0 -13 0 -3.20 4.10 1 -12 0 22.40 3.90 2 -11 0 2.30 4.20 -2 11 0 10.90 3.40 3 -10 0 76.59 9.60 -3 10 0 77.19 6.80 4 -9 0 2.80 8.70 -4 9 0 2.20 4.60 -1 -15 0 9.60 5.00 -1 -15 0 19.50 7.30 0 -14 0 13.60 5.00 1 -13 0 7.30 4.50 2 -12 0 17.30 5.30 3 -11 0 8.10 7.40 -3 11 0 6.50 4.60 0 -15 0 2.60 5.40 1 -14 0 36.10 7.50 3 -12 0 -3.50 7.30 -3 12 0 -9.30 5.00 1 -15 0 1.40 6.80 2 -14 -1 2.90 7.20 1 -15 -1 -0.70 6.60 3 -12 -1 41.50 8.80 2 -13 -1 -2.50 6.40 1 -14 -1 20.40 6.60 0 -15 -1 0.70 5.80 -3 11 1 5.70 4.60 3 -11 -1 4.40 7.20 2 -12 -1 0.70 5.10 1 -13 -1 11.10 4.70 0 -14 -1 -2.10 4.70 -1 -15 -1 11.60 6.80 -1 -15 -1 -5.60 4.90 -4 9 1 1.10 4.60 4 -9 -1 -1.90 8.50 -3 10 1 7.90 4.10 3 -10 -1 -0.70 5.50 2 -11 -1 14.40 4.40 1 -12 -1 -1.20 3.60 0 -13 -1 25.70 4.50 0 -13 -1 30.40 4.70 -1 -14 -1 5.60 5.90 -1 -14 -1 -2.80 4.10 -4 8 1 17.00 4.50 4 -8 -1 8.50 8.80 -3 9 1 0.10 3.20 3 -9 -1 -4.90 4.80 -2 10 1 22.70 3.50 2 -10 -1 22.40 4.00 1 -11 -1 106.49 7.30 0 -12 -1 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-3 3 -16 -16.40 8.90 -3 3 -16 9.00 6.10 0 -7 16 1.80 3.40 0 7 -16 1.70 12.60 0 7 -16 -2.00 4.40 -1 6 -16 5.70 4.80 -1 6 -16 -9.50 10.80 -2 5 -16 7.30 5.00 -2 5 -16 5.10 9.90 0 -8 16 4.00 4.00 0 8 -16 5.10 4.90 0 8 -16 -7.90 13.70 -1 7 -16 -6.50 11.90 -1 7 -16 2.50 5.00 -2 6 -16 -5.40 5.10 -2 6 -16 6.20 11.30 -1 8 -16 17.60 14.10 -1 8 -16 0.80 5.40 -2 7 -16 4.40 5.80 0 -7 -17 33.20 10.00 1 -5 -17 10.60 11.70 0 -6 -17 -11.70 8.40 -1 -7 -17 47.10 9.40 1 -4 -17 -16.80 9.40 0 -5 -17 21.00 8.40 -1 -6 -17 6.10 7.40 -1 3 17 10.70 5.70 1 -3 -17 -8.50 9.30 -1 -5 -17 17.70 7.20 -2 1 17 2.50 8.60 -2 1 17 -1.50 8.40 -1 2 17 6.20 5.30 -1 2 17 6.60 5.90 1 -2 -17 -0.40 9.90 0 -3 -17 5.20 7.40 -1 -4 -17 -8.50 6.50 -2 -5 -17 9.40 7.80 -2 0 17 -2.30 8.20 -2 0 17 -1.50 8.10 -1 1 17 4.60 5.70 -1 1 17 3.60 4.90 1 -1 -17 8.40 9.50 0 -2 -17 -0.60 7.50 -1 -3 -17 -0.10 6.60 -2 -4 -17 1.50 6.60 -2 -1 17 -8.20 7.70 -1 0 17 -6.60 4.50 1 0 -17 18.20 9.70 0 -1 -17 50.29 9.70 -1 -2 -17 8.50 5.80 -1 -2 -17 1.40 6.70 -2 -3 -17 1.50 6.80 -1 -1 17 3.80 4.70 1 1 -17 8.90 10.60 0 0 -17 -14.40 8.00 -1 -1 -17 -10.20 7.00 -1 -1 -17 -2.00 5.20 -2 -2 -17 12.50 7.00 -2 -2 -17 -2.80 6.00 -1 -2 17 7.30 4.80 1 2 -17 -14.90 10.40 0 1 -17 35.80 9.40 -1 0 -17 2.40 5.10 -1 0 -17 5.40 7.40 -2 -1 -17 4.10 6.90 -2 -1 -17 1.10 5.90 -1 -3 17 2.90 4.50 1 3 -17 1.10 12.30 0 2 -17 5.90 9.70 -1 1 -17 -12.40 7.80 -1 1 -17 -3.50 4.90 -2 0 -17 -10.20 7.40 -2 0 -17 -3.80 5.70 1 4 -17 19.60 13.50 0 3 -17 25.30 11.30 -1 2 -17 -5.90 8.60 -1 2 -17 9.00 5.00 -2 1 -17 8.70 7.90 -2 1 -17 8.00 5.70 -1 -5 17 3.30 4.90 1 5 -17 7.20 14.50 0 4 -17 0.60 11.30 -1 3 -17 1.40 4.60 -1 3 -17 10.70 9.40 -2 2 -17 11.50 8.30 -2 2 -17 9.30 5.70 -1 -6 17 5.90 5.10 0 5 -17 2.40 12.30 -1 4 -17 7.40 4.70 -1 4 -17 4.40 9.80 -2 3 -17 22.10 9.60 -2 3 -17 9.00 6.00 0 6 -17 -1.60 13.60 -1 5 -17 7.10 11.60 -2 4 -17 -1.20 5.50 -2 4 -17 6.60 10.30 0 7 -17 0.00 14.70 -1 6 -17 4.90 12.70 -1 6 -17 12.90 5.40 -2 5 -17 8.30 6.00 -2 5 -17 18.70 11.90 -1 7 -17 35.10 6.40 0 -5 -18 1.10 10.40 1 -3 -18 23.80 12.70 0 -4 -18 44.30 10.80 -1 -5 -18 -0.10 8.50 1 -2 -18 42.20 13.60 0 -3 -18 29.10 10.10 -1 -4 -18 -0.90 8.30 1 -1 -18 -4.30 11.50 0 -2 -18 21.40 9.80 -1 -3 -18 2.80 6.30 -1 -3 -18 9.60 7.70 1 0 -18 5.40 12.60 0 -1 -18 18.00 9.40 -1 -2 -18 7.00 6.30 -1 -2 -18 19.40 8.40 -1 -1 18 0.10 8.10 1 1 -18 -0.30 12.20 0 0 -18 22.70 10.60 -1 -1 -18 34.80 9.70 -1 -1 -18 33.70 6.40 -2 -2 -18 1.10 8.50 -2 -2 -18 4.20 7.20 -1 -2 18 37.00 6.20 1 2 -18 22.30 14.20 -1 0 -18 18.10 9.70 -1 0 -18 7.10 5.70 -2 -1 -18 23.90 9.10 -2 -1 -18 14.60 7.30 -1 -3 18 10.40 5.10 1 3 -18 -8.90 14.70 0 2 -18 15.50 11.60 -1 1 -18 19.40 5.80 -1 1 -18 40.40 10.10 -2 0 -18 4.20 6.90 -2 0 -18 14.90 9.10 0 3 -18 9.10 11.90 -1 2 -18 13.30 10.00 -1 2 -18 4.10 5.60 -2 1 -18 -0.90 9.60 -2 1 -18 3.80 6.60 0 4 -18 44.00 13.50 -1 3 -18 1.60 10.90 -1 3 -18 2.30 5.20 -2 2 -18 2.80 10.50 -2 2 -18 2.80 6.50 0 5 -18 -24.30 13.50 -1 4 -18 3.70 5.40 -1 4 -18 -13.60 11.50 -1 5 -18 6.80 12.90 -1 5 -18 1.40 5.50 0 -1 -19 12.00 12.40 -1 -2 -19 4.10 10.40 0 0 -19 7.80 12.60 -1 -1 -19 -0.80 11.10 -1 -1 -19 2.60 6.50 0 1 -19 14.40 14.10 -1 0 -19 -12.90 11.40 -1 0 -19 6.60 6.40 -1 1 -19 24.40 12.40 -1 1 -19 7.30 6.40 -1 2 -19 9.20 5.70 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 50027 _olex2_submission_special_instructions 'No special instructions were received' 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 C00B C 0.8482(5) 0.03304(15) 0.37897(13) 0.0502(5) Uani 1 1 d . . . . . C00C C 0.8484(5) 0.46728(15) -0.12093(13) 0.0508(5) Uani 1 1 d . . . . . C00D C 0.3767(5) 0.34889(15) 0.35857(14) 0.0526(5) Uani 1 1 d . . . . . H00D H 0.2728 0.4184 0.3538 0.063 Uiso 1 1 calc R . . . . C00E C 0.3764(5) 0.15081(15) -0.14111(14) 0.0533(5) Uani 1 1 d . . . . . H00E H 0.2734 0.0813 -0.1456 0.064 Uiso 1 1 calc R . . . . C00F C 0.2896(5) 0.13869(15) 0.02695(14) 0.0533(5) Uani 1 1 d . . . . . C00G C 0.2905(5) 0.36117(15) 0.52686(14) 0.0525(5) Uani 1 1 d . . . . . C00H C 0.6465(5) 0.18767(16) 0.28667(13) 0.0545(5) Uani 1 1 d . . . . . H00H H 0.7233 0.1493 0.2337 0.065 Uiso 1 1 calc R . . . . C00I C 0.6472(5) 0.31218(16) -0.21338(13) 0.0545(5) Uani 1 1 d . . . . . H00I H 0.7247 0.3504 -0.2664 0.065 Uiso 1 1 calc R . . . . C00J C 0.4914(6) 0.20883(16) -0.21962(14) 0.0612(5) Uani 1 1 d . . . . . H00J H 0.4638 0.1782 -0.2770 0.073 Uiso 1 1 calc R . . . . C00K C 0.4913(5) 0.29105(16) 0.28032(14) 0.0599(5) Uani 1 1 d . . . . . H00K H 0.4639 0.3219 0.2229 0.072 Uiso 1 1 calc R . . . . C002 C 0.6875(4) 0.14119(13) 0.37264(12) 0.0428(4) Uani 1 1 d . . . . . C004 C 0.6874(4) 0.35855(13) -0.12754(12) 0.0426(4) Uani 1 1 d . . . . . C005 C 0.4175(4) 0.30245(13) 0.44471(12) 0.0430(4) Uani 1 1 d . . . . . C006 C 0.5738(4) 0.19856(13) 0.45226(12) 0.0432(4) Uani 1 1 d . . . . . H006 H 0.6020 0.1678 0.5097 0.052 Uiso 1 1 calc R . . . . C007 C 0.4166(4) 0.19750(13) -0.05544(12) 0.0436(4) Uani 1 1 d . . . . . C008 C 0.5742(4) 0.30169(13) -0.04784(12) 0.0432(4) Uani 1 1 d . . . . . H008 H 0.6027 0.3323 0.0095 0.052 Uiso 1 1 calc R . . . . N00A N 0.1837(5) 0.09288(14) 0.09218(13) 0.0740(5) Uani 1 1 d . . . . . N001 N 0.9742(5) -0.05339(14) 0.38424(13) 0.0688(5) Uani 1 1 d . . . . . N003 N 0.9752(5) 0.55346(14) -0.11600(13) 0.0685(5) Uani 1 1 d . . . . . N009 N 0.1843(5) 0.40699(15) 0.59222(14) 0.0746(5) 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 C00B 0.0478(11) 0.0485(11) 0.0548(12) -0.0042(8) -0.0061(9) -0.0018(8) C00C 0.0482(11) 0.0488(11) 0.0555(12) 0.0070(8) -0.0056(9) 0.0008(8) C00D 0.0514(11) 0.0450(10) 0.0617(13) 0.0085(9) -0.0063(10) 0.0004(8) C00E 0.0516(12) 0.0465(10) 0.0619(13) -0.0073(9) -0.0050(10) -0.0025(8) C00F 0.0525(12) 0.0485(10) 0.0586(13) 0.0015(9) -0.0011(10) -0.0024(8) C00G 0.0510(12) 0.0477(10) 0.0580(13) -0.0017(9) 0.0002(10) 0.0002(8) C00H 0.0550(12) 0.0606(12) 0.0472(11) -0.0048(9) -0.0001(9) -0.0007(9) C00I 0.0550(12) 0.0615(12) 0.0463(11) 0.0061(9) 0.0005(9) -0.0027(9) C00J 0.0698(14) 0.0657(12) 0.0485(12) -0.0112(9) -0.0060(10) -0.0041(10) C00K 0.0682(14) 0.0637(12) 0.0481(12) 0.0111(9) -0.0064(10) 0.0027(10) C002 0.0372(9) 0.0422(9) 0.0491(11) -0.0010(7) -0.0042(8) -0.0048(7) C004 0.0367(9) 0.0408(9) 0.0504(11) 0.0018(7) -0.0040(8) 0.0036(7) C005 0.0369(9) 0.0418(9) 0.0501(11) -0.0002(7) -0.0017(8) -0.0041(7) C006 0.0402(10) 0.0443(9) 0.0452(10) 0.0029(7) -0.0050(8) -0.0062(7) C007 0.0379(9) 0.0432(9) 0.0491(11) 0.0002(8) -0.0001(8) 0.0034(7) C008 0.0412(10) 0.0431(9) 0.0453(10) -0.0035(7) -0.0041(8) 0.0037(7) N00A 0.0850(14) 0.0678(11) 0.0671(12) 0.0107(9) 0.0082(10) -0.0115(10) N001 0.0741(13) 0.0573(10) 0.0755(13) -0.0066(8) -0.0093(10) 0.0079(9) N003 0.0743(13) 0.0547(10) 0.0770(13) 0.0087(8) -0.0104(10) -0.0108(9) N009 0.0855(14) 0.0686(12) 0.0680(13) -0.0090(9) 0.0067(10) 0.0096(10) 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' 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 N001 C00B C002 179.6(2) . . ? N003 C00C C004 179.7(2) . . ? C00K C00D H00D 120.2 . . ? C00K C00D C005 119.68(18) . . ? C005 C00D H00D 120.2 . . ? C00J C00E H00E 120.3 . . ? C00J C00E C007 119.41(18) . . ? C007 C00E H00E 120.3 . . ? N00A C00F C007 178.8(2) . . ? N009 C00G C005 178.9(2) . . ? C00K C00H H00H 120.1 . . ? C00K C00H C002 119.79(18) . . ? C002 C00H H00H 120.1 . . ? C00J C00I H00I 120.1 . . ? C00J C00I C004 119.86(17) . . ? C004 C00I H00I 120.1 . . ? C00E C00J C00I 120.57(19) . . ? C00E C00J H00J 119.7 . . ? C00I C00J H00J 119.7 . . ? C00D C00K C00H 120.59(18) . . ? C00D C00K H00K 119.7 . . ? C00H C00K H00K 119.7 . . ? C00H C002 C00B 119.62(17) . . ? C00H C002 C006 120.33(17) . . ? C006 C002 C00B 120.05(16) . . ? C00I C004 C00C 119.90(16) . . ? C008 C004 C00C 119.58(16) . . ? C008 C004 C00I 120.52(17) . . ? C00D C005 C00G 120.01(17) . . ? C006 C005 C00D 120.41(17) . . ? C006 C005 C00G 119.56(16) . . ? C002 C006 H006 120.4 . . ? C005 C006 C002 119.19(16) . . ? C005 C006 H006 120.4 . . ? C00E C007 C00F 119.78(17) . . ? C00E C007 C008 120.79(17) . . ? C008 C007 C00F 119.42(17) . . ? C004 C008 C007 118.85(17) . . ? C004 C008 H008 120.6 . . ? C007 C008 H008 120.6 . . ? 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 C00B C002 1.443(3) . ? C00B N001 1.150(2) . ? C00C C004 1.454(3) . ? C00C N003 1.150(2) . ? C00D H00D 0.9300 . ? C00D C00K 1.382(3) . ? C00D C005 1.395(3) . ? C00E H00E 0.9300 . ? C00E C00J 1.385(3) . ? C00E C007 1.392(3) . ? C00F C007 1.448(3) . ? C00F N00A 1.148(3) . ? C00G C005 1.446(3) . ? C00G N009 1.151(3) . ? C00H H00H 0.9300 . ? C00H C00K 1.383(3) . ? C00H C002 1.393(3) . ? C00I H00I 0.9300 . ? C00I C00J 1.387(3) . ? C00I C004 1.393(3) . ? C00J H00J 0.9300 . ? C00K H00K 0.9300 . ? C002 C006 1.395(3) . ? C004 C008 1.391(3) . ? C005 C006 1.392(3) . ? C006 H006 0.9300 . ? C007 C008 1.401(3) . ? C008 H008 0.9300 . ?