#------------------------------------------------------------------------------ #$Date: 2020-04-22 23:50:41 +0300 (Wed, 22 Apr 2020) $ #$Revision: 251056 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557861.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_1557861 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 monoclinic _space_group_IT_number 7 _space_group_name_Hall 'P -2yac' _space_group_name_H-M_alt 'P 1 n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-03-22 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324) ; _cell_angle_alpha 90 _cell_angle_beta 119.046(17) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.125(14) _cell_length_b 3.844(4) _cell_length_c 14.305(15) _cell_measurement_reflns_used 150 _cell_measurement_temperature 101(2) _cell_measurement_theta_max 0.992 _cell_measurement_theta_min 0.991 _cell_volume 679.0(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 100.99 _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.971 _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 0.0459 _diffrn_reflns_av_unetI/netI 0.0814 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.971 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2735 _diffrn_reflns_point_group_measured_fraction_full 0.799 _diffrn_reflns_point_group_measured_fraction_max 0.782 _diffrn_reflns_theta_full 24.992 _diffrn_reflns_theta_max 24.992 _diffrn_reflns_theta_min 1.662 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _exptl_absorpt_coefficient_mu 0.079 _exptl_crystal_density_diffrn 1.253 _exptl_crystal_description needle _exptl_crystal_F_000 264 _exptl_crystal_size_max 1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.559 _refine_diff_density_min -0.536 _refine_diff_density_rms 0.105 _refine_ls_abs_structure_details ; Flack x determined using 215 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -3.0(10) _refine_ls_extinction_coef 0.26(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 1547 _refine_ls_number_restraints 122 _refine_ls_restrained_S_all 1.161 _refine_ls_R_factor_all 0.1345 _refine_ls_R_factor_gt 0.1100 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1573P)^2^+1.9785P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3139 _refine_ls_wR_factor_ref 0.3359 _reflns_Friedel_coverage 0.607 _reflns_Friedel_fraction_full 0.604 _reflns_Friedel_fraction_max 0.592 _reflns_number_gt 1211 _reflns_number_total 1547 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jp0c01762_si_003.cif _cod_data_source_block 1 _cod_database_code 1557861 _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 0.992 _shelx_estimated_absorpt_t_min 0.925 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.670(7) 0.330(7) 2. Fixed Uiso At 1.2 times of: All C(H) groups 3. Uiso/Uaniso restraints and constraints All non-hydrogen atoms restrained to be isotropic: with sigma of 0.003 and sigma for terminal atoms of 0.006 4.a Aromatic/amide H refined with riding coordinates: C00A(H00A), C00E(H00E), C00F(H00F), C008(H008), C00B(H00B), C00I(H00I), C00J(H00J), C009(H009) ; _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1_a.res in Pn REM Old TITL 1_a.res in Pn REM SHELXT solution in Pn REM R1 0.297, Rweak 0.045, Alpha 0.070, Orientation as input REM Flack x = -0.367 ( 2.319 ) from Parsons' quotients REM Formula found by SHELXT: C16 N6 CELL 0.71073 14.1254 3.8437 14.3046 90 119.046 90 ZERR 4 0.0143 0.004 0.0151 0 0.017 0 LATT -1 SYMM 0.5+X,-Y,0.5+Z SFAC C H N UNIT 32 16 8 ISOR 0.003 0.006 L.S. 4 PLAN 20 SIZE 0.1 0.1 1 TEMP -172.16 BOND $H list 4 fmap 2 acta TWIN -0.025 0 0.975 0 -1 0 1.025 0 0.025 2 OMIT 0 50 REM REM REM WGHT 0.157300 1.978500 EXTI 0.255374 BASF 0.32982 FVAR 2.06005 C00A 1 -0.684010 -0.070540 -0.891653 11.00000 0.05064 0.04673 = 0.04937 -0.00027 0.02663 0.00328 AFIX 43 H00A 2 -0.723259 -0.088132 -0.967393 11.00000 -1.20000 AFIX 0 C00E 1 -0.736051 0.083682 -0.838706 11.00000 0.05801 0.05859 = 0.06018 0.00087 0.03241 -0.00041 AFIX 43 H00E 2 -0.804417 0.195591 -0.876289 11.00000 -1.20000 AFIX 0 C00F 1 -0.575953 -0.059877 -0.674019 11.00000 0.04022 0.02998 = 0.03485 0.00241 0.02067 -0.00051 AFIX 43 H00F 2 -0.539385 -0.058051 -0.598060 11.00000 -1.20000 AFIX 0 C00G 1 -0.414735 -0.305807 -0.670807 11.00000 0.04754 0.04144 = 0.04325 -0.00374 0.02529 0.00202 C001 1 -0.580110 -0.195807 -0.839593 11.00000 0.04419 0.04087 = 0.04322 0.00070 0.02637 0.00002 C002 1 -0.526916 -0.341005 -0.896342 11.00000 0.04537 0.03434 = 0.03793 0.00101 0.02213 -0.00141 C005 1 -0.521734 -0.183482 -0.725797 11.00000 0.03453 0.01966 = 0.03000 0.00148 0.01814 0.00120 C008 1 -0.679871 0.059546 -0.727691 11.00000 0.03857 0.02890 = 0.03583 -0.00233 0.02079 0.00328 AFIX 43 H008 2 -0.714828 0.128077 -0.688230 11.00000 -1.20000 AFIX 0 N003 3 -0.486541 -0.461961 -0.943060 11.00000 0.05691 0.04261 = 0.05485 0.00352 0.03492 0.00330 N007 3 -0.325381 -0.453567 -0.623721 11.00000 0.06587 0.06238 = 0.06671 -0.00716 0.04051 0.00162 C00B 1 -0.734077 -1.062563 -0.338010 11.00000 0.03614 0.02948 = 0.04044 0.00083 0.01652 0.00180 AFIX 43 H00B 2 -0.808411 -1.125863 -0.375491 11.00000 -1.20000 AFIX 0 C00C 1 -0.523660 -0.794193 -0.227683 11.00000 0.03581 0.02825 = 0.03693 -0.00140 0.02061 0.00325 C00D 1 -0.414443 -0.632043 -0.171000 11.00000 0.03467 0.02800 = 0.02866 -0.00148 0.01857 0.00003 C00H 1 -0.527543 -0.656405 -0.396962 11.00000 0.03962 0.03172 = 0.03355 -0.00302 0.01894 0.00144 C00I 1 -0.685942 -0.951168 -0.393109 11.00000 0.03488 0.02340 = 0.03455 -0.00335 0.01338 -0.00135 AFIX 43 H00I 2 -0.722955 -0.972246 -0.468798 11.00000 -1.20000 AFIX 0 C00J 1 -0.679787 -1.087052 -0.230908 11.00000 0.05231 0.05331 = 0.05608 -0.00146 0.03256 0.00110 AFIX 43 H00J 2 -0.711407 -1.201594 -0.193932 11.00000 -1.20000 AFIX 0 C00K 1 -0.579945 -0.800915 -0.340677 11.00000 0.02954 0.01651 = 0.02793 0.00136 0.01522 -0.00068 C009 1 -0.571101 -0.935022 -0.171584 11.00000 0.05257 0.05109 = 0.05289 -0.00142 0.02880 -0.00168 AFIX 43 H009 2 -0.533867 -0.933475 -0.095619 11.00000 -1.20000 AFIX 0 N004 3 -0.327839 -0.534860 -0.125971 11.00000 0.05131 0.02482 = 0.04174 -0.00342 0.02400 -0.00225 N006 3 -0.487249 -0.549758 -0.444169 11.00000 0.05088 0.04610 = 0.04784 0.00561 0.03099 -0.00842 HKLF 4 REM 1_a.res in Pn REM R1 = 0.1100 for 1211 Fo > 4sig(Fo) and 0.1345 for all 1547 data REM 183 parameters refined using 122 restraints END WGHT 0.1573 1.9785 REM Highest difference peak 0.559, deepest hole -0.536, 1-sigma level 0.105 Q1 1 -0.5461 -0.7817 -0.2858 11.00000 0.05 0.56 Q2 1 -0.5464 -0.1967 -0.7783 11.00000 0.05 0.47 Q3 1 -0.7176 -1.0736 -0.2878 11.00000 0.05 0.44 Q4 1 -0.6937 -0.4423 -0.8232 11.00000 0.05 0.42 Q5 1 -0.4159 -0.0422 -0.6683 11.00000 0.05 0.40 Q6 1 -0.7141 0.0779 -0.7819 11.00000 0.05 0.37 Q7 1 -0.6857 -1.4175 -0.2259 11.00000 0.05 0.35 Q8 1 -0.6434 -0.4515 -0.7428 11.00000 0.05 0.34 Q9 1 -0.6973 -1.5480 -0.2180 11.00000 0.05 0.34 Q10 1 -0.4260 -0.9498 -0.1259 11.00000 0.05 0.34 Q11 1 -0.4315 -0.0459 -0.4948 11.00000 0.05 0.33 Q12 1 -0.4583 -0.0157 -0.6034 11.00000 0.05 0.33 Q13 1 -0.6983 0.5050 -0.7458 11.00000 0.05 0.32 Q14 1 -0.5208 -0.4977 -0.2283 11.00000 0.05 0.32 Q15 1 -0.6007 -0.4007 -0.7885 11.00000 0.05 0.32 Q16 1 -0.4115 -0.3953 -0.1828 11.00000 0.05 0.31 Q17 1 -0.3864 -1.0253 -0.0520 11.00000 0.05 0.30 Q18 1 -0.4514 -0.2980 -0.7214 11.00000 0.05 0.30 Q19 1 -0.5855 -1.2671 -0.1715 11.00000 0.05 0.29 Q20 1 -0.4657 -1.0186 -0.0810 11.00000 0.05 0.29 ; _shelx_res_checksum 35799 _shelx_hkl_file ; -2 0 0 6599.34 544.85 3 0 0 13.40 1.90 4 0 0 8332.07 686.73 5 0 0 4.00 1.50 6 0 0 3298.27 272.07 7 0 0 0.40 1.80 8 0 0 751.52 62.29 9 0 0 -0.80 2.50 10 0 0 243.58 20.70 11 0 0 -0.50 4.00 12 0 0 470.95 39.70 13 0 0 4.70 4.20 14 0 0 64.09 8.10 15 0 0 -2.80 6.10 16 0 0 -1.10 6.90 0 -1 0 2302.07 189.88 1 -1 0 3493.15 302.07 -1 1 0 3828.82 302.07 -2 1 0 6939.71 572.34 3 -1 0 672.13 51.99 3 -1 0 600.04 51.69 3 1 0 602.64 51.89 4 -1 0 962.50 80.19 4 -1 0 990.10 80.49 4 1 0 959.90 80.39 5 -1 0 691.43 53.69 5 -1 0 664.43 53.99 5 1 0 589.04 53.79 6 -1 0 3443.56 289.57 6 -1 0 3764.92 289.87 6 1 0 3326.47 289.67 7 -1 0 5.60 3.30 7 -1 0 3.50 2.10 7 1 0 1.00 2.10 8 -1 0 401.26 35.10 8 -1 0 428.46 34.50 8 1 0 410.26 34.60 9 -1 0 16.40 5.10 9 -1 0 18.30 3.40 9 1 0 8.90 3.50 10 -1 0 236.18 24.30 10 -1 0 304.37 23.70 10 1 0 292.47 23.90 11 -1 0 4.70 3.70 11 -1 0 15.70 6.20 11 1 0 5.50 3.70 12 -1 0 80.39 9.60 12 1 0 86.19 8.60 13 -1 0 7.50 4.90 14 -1 0 39.50 11.10 14 -1 0 48.60 8.30 14 1 0 61.09 7.70 15 -1 0 0.50 6.20 15 1 0 -1.50 5.30 16 -1 0 50.39 10.50 16 1 0 49.99 9.10 1 -2 0 258.77 22.10 2 -2 0 1485.45 126.29 2 2 0 1567.24 126.29 3 -2 0 166.98 14.90 3 2 0 167.58 14.60 4 -2 0 672.13 54.59 4 2 0 635.44 54.49 5 -2 0 14.20 3.80 5 2 0 5.40 3.10 6 -2 0 646.54 54.89 6 -2 0 668.53 55.19 6 2 0 663.53 55.09 7 -2 0 61.09 6.70 7 -2 0 57.49 7.00 7 2 0 55.79 7.30 8 -2 0 379.76 35.90 8 -2 0 414.96 35.50 8 2 0 469.65 35.70 9 -2 0 6.00 4.40 9 2 0 6.10 3.30 10 -2 0 61.89 9.30 10 -2 0 59.89 7.60 11 -2 0 4.80 5.10 11 2 0 5.20 4.20 12 -2 0 58.59 11.80 12 -2 0 62.69 9.90 13 -2 0 -7.00 10.90 13 -2 0 8.10 6.50 13 2 0 0.80 5.60 14 -2 0 40.70 7.90 14 -2 0 28.50 14.40 15 -2 0 27.90 15.50 15 2 0 14.20 7.50 1 3 0 16.80 4.10 2 -3 0 50.49 7.10 2 3 0 40.20 5.80 3 -3 0 817.22 64.49 3 3 0 722.53 64.29 4 -3 0 559.54 45.20 4 3 0 509.55 45.10 5 -3 0 38.60 6.30 6 -3 0 222.08 20.10 6 3 0 226.18 19.90 7 -3 0 363.46 28.30 7 3 0 283.87 27.90 8 -3 0 525.15 42.70 8 3 0 471.05 42.20 9 3 0 119.89 12.20 10 3 0 180.88 17.00 11 -3 0 63.29 13.20 12 -3 0 32.50 12.80 12 3 0 29.30 7.70 13 -3 0 18.50 15.50 13 3 0 16.30 8.90 0 4 0 25.10 4.90 1 4 0 66.99 7.90 -1 4 0 68.89 8.10 2 4 0 6.50 4.00 3 -4 0 113.59 12.50 3 4 0 116.69 11.50 4 -4 0 51.89 8.60 4 4 0 56.69 7.60 5 -4 0 164.58 15.60 5 4 0 144.99 14.80 6 -4 0 56.29 10.00 6 4 0 67.19 9.10 7 -4 0 94.09 12.30 7 4 0 85.79 11.20 8 -4 0 75.29 12.40 8 4 0 58.89 10.50 9 4 0 453.15 39.60 10 -4 0 52.89 13.40 10 4 0 29.50 9.90 0 5 0 0.10 5.80 1 5 0 6.00 5.60 1 5 0 0.90 11.10 -1 5 0 7.10 14.60 -1 5 0 6.30 5.80 -2 5 0 121.49 13.00 2 5 0 106.49 12.60 3 5 0 35.20 7.00 16 0 -1 3.60 6.30 15 0 -1 -1.10 5.30 14 0 -1 0.90 4.70 13 0 -1 11.70 4.60 12 0 -1 11.20 4.80 11 0 -1 1.60 3.00 10 0 -1 3.70 2.70 9 0 -1 0.50 3.00 9 0 -1 1.70 2.30 8 0 -1 6.30 2.10 7 0 -1 2.90 2.00 7 0 -1 11.30 2.20 6 0 -1 5.30 1.60 6 0 -1 0.30 1.80 5 0 -1 8.50 1.70 4 0 -1 -1.40 1.00 4 0 -1 -2.10 1.10 -4 0 1 -3.10 0.80 3 0 -1 -2.50 0.80 -3 0 1 -1.90 0.60 3 0 -1 -1.30 0.80 -2 0 1 -6.20 0.80 2 0 -1 -6.20 0.90 2 0 -1 -5.60 0.90 -2 0 1 -6.50 0.80 1 0 -1 5.00 0.60 -1 0 -1 -7.70 0.70 1 0 1 -7.50 0.80 2 0 1 -2.80 0.80 3 0 1 3.70 1.50 4 0 1 2.20 1.30 5 0 1 53.89 5.00 6 0 1 1.80 1.80 7 0 1 1.80 1.90 8 0 1 15.10 3.00 9 0 1 0.40 2.80 10 0 1 -1.50 3.50 11 0 1 0.60 4.10 12 0 1 6.70 4.00 13 0 1 2.80 4.50 14 0 1 9.50 5.50 15 0 1 8.40 6.60 16 -1 -1 62.79 8.90 16 -1 -1 32.20 15.30 16 1 -1 48.00 8.70 15 -1 -1 10.20 5.90 15 -1 -1 -13.10 11.30 15 1 -1 1.10 5.50 14 -1 -1 27.70 6.10 14 -1 -1 30.70 9.70 14 1 -1 27.00 5.60 13 -1 -1 4.00 7.50 13 -1 -1 3.20 5.30 13 1 -1 6.20 4.40 12 -1 -1 143.29 13.70 12 1 -1 159.68 13.70 11 -1 -1 9.80 5.30 11 -1 -1 17.30 3.90 11 1 -1 16.00 4.20 10 -1 -1 20.80 4.90 10 -1 -1 28.60 4.10 10 1 -1 23.80 4.60 9 -1 -1 22.50 3.60 9 -1 -1 17.00 4.30 9 1 -1 20.90 3.60 8 -1 -1 231.98 19.60 8 -1 -1 238.58 20.40 8 1 -1 229.98 19.90 7 -1 -1 79.69 6.80 7 1 -1 70.29 7.10 6 -1 -1 34.80 3.70 6 -1 -1 34.20 4.70 6 1 -1 40.50 4.20 5 -1 -1 245.28 19.40 5 1 -1 211.28 19.30 4 -1 -1 576.34 49.40 4 1 -1 612.34 49.40 3 -1 -1 357.66 27.50 3 1 -1 299.67 27.50 -2 1 1 9634.14 794.52 1 1 -1 949.60 78.79 0 -1 1 6074.89 493.65 0 1 -1 5897.41 493.55 1 -1 1 1826.02 135.99 -1 1 -1 1394.76 135.99 1 1 1 1714.03 135.99 2 -1 1 2030.90 177.68 2 -1 1 2267.87 177.78 2 1 1 2157.68 177.78 3 -1 1 85.49 7.70 3 -1 1 88.69 7.30 3 1 1 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17.80 0 2 15 48.50 11.20 0 2 15 27.80 18.60 -10 3 15 45.90 21.20 9 3 -15 2.30 5.00 -9 3 15 11.60 19.40 8 3 -15 27.80 6.10 -8 3 15 38.20 18.80 -7 3 15 14.30 16.60 7 3 -15 0.90 5.20 -6 3 15 42.70 17.30 5 3 -15 -1.80 5.50 -5 3 15 1.50 16.70 -4 3 15 -3.10 17.10 16 0 -16 3.80 8.50 15 0 -16 -2.70 7.30 14 0 -16 125.39 14.30 13 0 -16 6.60 6.60 12 0 -16 42.30 7.90 11 0 -16 0.20 5.40 10 0 -16 25.90 5.90 9 0 -16 55.79 7.90 -6 0 16 348.17 32.10 -5 0 16 0.90 9.10 -4 0 16 59.29 11.10 -3 0 16 17.30 9.50 -2 0 16 53.69 11.50 -1 0 16 22.10 10.30 0 0 16 33.80 10.80 1 0 16 9.90 11.90 15 -1 -16 57.29 12.40 15 1 -16 76.09 10.40 14 -1 -16 19.20 8.80 14 1 -16 30.10 6.90 13 -1 -16 15.40 7.70 13 1 -16 4.70 6.00 12 -1 -16 218.38 21.80 12 1 -16 250.67 21.30 11 -1 -16 66.49 9.70 11 1 -16 49.40 8.00 10 1 -16 31.80 6.20 -10 1 16 17.50 13.90 9 1 -16 43.00 6.70 -9 1 16 34.80 14.00 -7 1 16 38.60 13.60 -7 1 16 23.40 15.90 7 1 -16 15.20 4.70 -6 1 16 99.29 13.90 -6 1 16 91.99 19.40 6 1 -16 104.49 10.60 -5 1 16 26.00 9.40 5 1 -16 6.20 5.00 -5 1 16 9.70 16.90 -4 -1 16 135.99 19.30 4 1 -16 161.38 14.90 -3 -1 16 24.40 10.40 -3 1 16 -0.20 8.40 -2 -1 16 29.40 12.30 -2 1 16 34.80 9.40 -1 -1 16 7.40 11.50 -1 1 16 5.10 9.80 0 -1 16 72.09 14.10 0 1 16 73.19 12.90 13 -2 -16 33.50 11.50 13 2 -16 48.40 8.30 -13 2 16 20.40 19.20 -12 2 16 60.69 18.10 12 2 -16 62.69 8.70 -11 2 16 13.70 17.10 11 2 -16 38.30 7.40 10 2 -16 142.39 13.80 -10 2 16 142.99 22.70 -9 2 16 78.29 19.30 9 2 -16 95.09 10.20 8 2 -16 136.49 12.60 -8 2 16 100.99 20.00 -7 2 16 1.90 15.80 -6 2 16 28.60 17.10 6 2 -16 56.19 7.90 -5 2 16 24.20 16.80 -4 2 16 13.20 11.10 -4 2 16 32.00 17.00 4 2 -16 48.90 8.20 3 2 -16 14.40 6.30 -3 2 16 37.00 18.60 -3 2 16 20.50 11.20 2 2 -16 20.00 7.10 -2 2 16 21.70 10.40 -2 2 16 1.60 18.90 15 0 -17 -8.00 8.20 14 0 -17 -0.50 7.80 13 0 -17 4.60 7.30 12 0 -17 -0.90 7.10 11 0 -17 -3.20 6.10 10 0 -17 -2.90 5.70 8 0 -17 4.80 5.90 -6 0 17 -8.60 13.10 -5 0 17 7.70 13.40 -4 0 17 9.70 12.60 -3 0 17 1.00 11.00 -2 0 17 1.80 13.30 -1 0 17 21.70 13.20 14 -1 -17 38.10 9.90 14 1 -17 30.40 8.10 13 -1 -17 1.90 9.10 13 1 -17 -0.80 6.30 12 -1 -17 38.00 9.40 12 1 -17 40.30 8.00 11 1 -17 1.70 5.80 -11 1 17 7.10 15.50 10 1 -17 96.39 11.10 -9 1 17 -11.50 15.80 9 1 -17 4.40 5.60 8 1 -17 68.69 9.20 -8 1 17 57.19 19.90 -7 1 17 -3.80 16.90 -7 1 17 8.10 18.40 7 1 -17 9.10 5.10 6 1 -17 155.78 13.40 -6 1 17 110.09 25.70 -6 1 17 97.69 16.60 -5 1 17 6.10 11.70 -4 1 17 51.99 11.70 -3 -1 17 -9.90 11.90 -2 -1 17 44.20 16.00 -2 1 17 37.10 11.80 -11 2 17 3.80 18.50 11 2 -17 0.40 6.30 10 2 -17 47.30 8.20 -10 2 17 45.20 19.80 9 2 -17 17.60 6.20 -9 2 17 13.50 18.80 8 2 -17 185.88 17.60 -7 2 17 -6.20 18.20 7 2 -17 11.50 5.70 6 2 -17 12.80 5.70 -6 2 17 -4.80 18.80 5 2 -17 1.00 5.60 -5 2 17 -3.10 19.10 13 0 -18 31.20 9.20 12 0 -18 505.65 43.60 11 0 -18 17.30 8.00 10 0 -18 125.49 14.60 9 0 -18 8.50 7.40 -5 0 18 41.70 18.00 -4 0 18 101.29 17.10 12 -1 -18 25.00 10.50 12 1 -18 20.80 7.20 11 1 -18 2.50 6.50 -11 1 18 -3.10 18.50 10 1 -18 215.98 20.30 -9 1 18 23.00 19.60 9 1 -18 18.10 7.00 -8 1 18 93.29 24.70 8 1 -18 145.09 14.60 -7 1 18 32.30 22.90 7 1 -18 20.30 7.20 -6 1 18 26.50 25.10 -5 1 18 15.70 13.40 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 60661 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y, 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 C00A C -0.6840(14) -0.071(4) -0.8917(13) 0.048(4) Uani 1 1 d . . . . . H00A H -0.7233 -0.0881 -0.9674 0.058 Uiso 1 1 calc R . . . . C00E C -0.7361(15) 0.084(4) -0.8387(14) 0.057(4) Uani 1 1 d . . . . . H00E H -0.8044 0.1956 -0.8763 0.069 Uiso 1 1 calc R . . . . C00F C -0.5760(11) -0.060(3) -0.6740(10) 0.034(3) Uani 1 1 d . . . . . H00F H -0.5394 -0.0581 -0.5981 0.041 Uiso 1 1 calc R . . . . C00G C -0.4147(12) -0.306(4) -0.6708(11) 0.043(3) Uani 1 1 d . . . . . C001 C -0.5801(12) -0.196(3) -0.8396(11) 0.041(3) Uani 1 1 d . . . . . C002 C -0.5269(11) -0.341(4) -0.8963(10) 0.038(3) Uani 1 1 d . . . . . C005 C -0.5217(10) -0.183(3) -0.7258(10) 0.027(3) Uani 1 1 d . . . . . C008 C -0.6799(11) 0.060(3) -0.7277(10) 0.033(3) Uani 1 1 d . . . . . H008 H -0.7148 0.1281 -0.6882 0.040 Uiso 1 1 calc R . . . . N003 N -0.4865(11) -0.462(4) -0.9431(10) 0.048(3) Uani 1 1 d . . . . . N007 N -0.3254(14) -0.454(5) -0.6237(13) 0.061(4) Uani 1 1 d . . . . . C00B C -0.7341(12) -1.063(3) -0.3380(11) 0.036(3) Uani 1 1 d . . . . . H00B H -0.8084 -1.1259 -0.3755 0.043 Uiso 1 1 calc R . . . . C00C C -0.5237(11) -0.794(3) -0.2277(11) 0.032(3) Uani 1 1 d . . . . . C00D C -0.4144(10) -0.632(3) -0.1710(10) 0.029(2) Uani 1 1 d . . . . . C00H C -0.5275(10) -0.656(3) -0.3970(10) 0.034(3) Uani 1 1 d . . . . . C00I C -0.6859(11) -0.951(3) -0.3931(10) 0.032(3) Uani 1 1 d . . . . . H00I H -0.7230 -0.9722 -0.4688 0.039 Uiso 1 1 calc R . . . . C00J C -0.6798(14) -1.087(4) -0.2309(13) 0.051(4) Uani 1 1 d . . . . . H00J H -0.7114 -1.2016 -0.1939 0.062 Uiso 1 1 calc R . . . . C00K C -0.5799(9) -0.801(2) -0.3407(9) 0.024(2) Uani 1 1 d . . . . . C009 C -0.5711(13) -0.935(4) -0.1716(13) 0.051(4) Uani 1 1 d . . . . . H009 H -0.5339 -0.9335 -0.0956 0.061 Uiso 1 1 calc R . . . . N004 N -0.3278(11) -0.535(3) -0.1260(10) 0.039(3) Uani 1 1 d . . . . . N006 N -0.4872(10) -0.550(4) -0.4442(10) 0.045(3) 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 C00A 0.051(5) 0.047(5) 0.049(5) 0.000(3) 0.027(3) 0.003(3) C00E 0.058(5) 0.059(5) 0.060(5) 0.001(3) 0.032(4) 0.000(3) C00F 0.040(4) 0.030(4) 0.035(4) 0.002(3) 0.021(3) -0.001(3) C00G 0.048(4) 0.041(4) 0.043(4) -0.004(3) 0.025(3) 0.002(3) C001 0.044(4) 0.041(4) 0.043(4) 0.001(3) 0.026(3) 0.000(3) C002 0.045(4) 0.034(4) 0.038(4) 0.001(3) 0.022(3) -0.001(3) C005 0.035(4) 0.020(4) 0.030(4) 0.001(3) 0.018(3) 0.001(3) C008 0.039(4) 0.029(4) 0.036(4) -0.002(3) 0.021(3) 0.003(3) N003 0.057(6) 0.043(5) 0.055(6) 0.004(5) 0.035(5) 0.003(5) N007 0.066(6) 0.062(7) 0.067(7) -0.007(5) 0.041(5) 0.002(5) C00B 0.036(4) 0.029(4) 0.040(4) 0.001(3) 0.017(3) 0.002(3) C00C 0.036(4) 0.028(4) 0.037(4) -0.001(3) 0.021(3) 0.003(3) C00D 0.035(4) 0.028(3) 0.029(4) -0.001(3) 0.019(3) 0.000(3) C00H 0.040(4) 0.032(4) 0.034(4) -0.003(3) 0.019(3) 0.001(3) C00I 0.035(4) 0.023(4) 0.035(4) -0.003(3) 0.013(3) -0.001(3) C00J 0.052(5) 0.053(6) 0.056(5) -0.001(3) 0.033(4) 0.001(3) C00K 0.030(4) 0.017(3) 0.028(4) 0.001(3) 0.015(3) -0.001(3) C009 0.053(5) 0.051(5) 0.053(5) -0.001(3) 0.029(4) -0.002(3) N004 0.051(5) 0.025(4) 0.042(5) -0.003(4) 0.024(4) -0.002(4) N006 0.051(5) 0.046(6) 0.048(5) 0.006(5) 0.031(4) -0.008(5) 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 C00E C00A H00A 118.2 . . ? C001 C00A H00A 118.2 . . ? C001 C00A C00E 123.6(15) . . ? C00A C00E H00E 122.4 . . ? C008 C00E C00A 115.2(15) . . ? C008 C00E H00E 122.4 . . ? C005 C00F H00F 118.7 . . ? C008 C00F H00F 118.7 . . ? C008 C00F C005 122.6(12) . . ? N007 C00G C005 172.3(16) . . ? C00A C001 C002 122.5(13) . . ? C00A C001 C005 118.8(12) . . ? C005 C001 C002 118.7(11) . . ? N003 C002 C001 178.4(15) . . ? C00F C005 C00G 122.7(12) . . ? C00F C005 C001 117.4(11) . . ? C00G C005 C001 119.9(11) . . ? C00E C008 H008 119.1 . . ? C00F C008 C00E 121.8(13) . . ? C00F C008 H008 119.1 . . ? C00I C00B H00B 119.2 . . ? C00I C00B C00J 121.5(14) . . ? C00J C00B H00B 119.2 . . ? C00K C00C C00D 119.3(11) . . ? C009 C00C C00D 121.0(13) . . ? C009 C00C C00K 119.7(12) . . ? N004 C00D C00C 174.5(13) . . ? N006 C00H C00K 177.8(14) . . ? C00B C00I H00I 119.2 . . ? C00B C00I C00K 121.5(12) . . ? C00K C00I H00I 119.2 . . ? C00B C00J H00J 120.3 . . ? C00B C00J C009 119.3(15) . . ? C009 C00J H00J 120.3 . . ? C00C C00K C00H 118.3(10) . . ? C00C C00K C00I 118.1(10) . . ? C00I C00K C00H 123.5(11) . . ? C00C C009 C00J 119.1(14) . . ? C00C C009 H009 120.4 . . ? C00J C009 H009 120.4 . . ? 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 C00A H00A 0.9500 . ? C00A C00E 1.42(2) . ? C00A C001 1.37(2) . ? C00E H00E 0.9500 . ? C00E C008 1.39(2) . ? C00F H00F 0.9500 . ? C00F C005 1.383(16) . ? C00F C008 1.364(19) . ? C00G C005 1.40(2) . ? C00G N007 1.24(2) . ? C001 C002 1.459(18) . ? C001 C005 1.424(16) . ? C002 N003 1.165(17) . ? C008 H008 0.9500 . ? C00B H00B 0.9500 . ? C00B C00I 1.337(18) . ? C00B C00J 1.34(2) . ? C00C C00D 1.487(19) . ? C00C C00K 1.413(15) . ? C00C C009 1.38(2) . ? C00D N004 1.134(17) . ? C00H C00K 1.443(16) . ? C00H N006 1.149(16) . ? C00I H00I 0.9500 . ? C00I C00K 1.431(17) . ? C00J H00J 0.9500 . ? C00J C009 1.47(2) . ? C009 H009 0.9500 . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.670(7) 2 0.330(7)