####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_CUNY2021 _audit_block_doi 10.5517/ccdc.csd.cc2brwww _database_code_depnum_ccdc_archive 'CCDC 2167919' loop_ _audit_author_name _audit_author_address 'Andrey A. Bardin' ;Arizona State University United States of America ; _audit_update_record ; 2022-04-21 deposited with the CCDC. 2022-07-12 downloaded from the CCDC. ; # start Validation Reply Form _vrf_RINTA01_CUNY2021 ; PROBLEM: The value of Rint is greater than 0.25 RESPONSE: electron diffraction data ; _vrf_PLAT020_CUNY2021 ; PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.319 Report RESPONSE: electron diffraction data ; _vrf_PLAT082_CUNY2021 ; PROBLEM: High R1 Value .................................. 0.22 Report RESPONSE: electron diffraction data ; _vrf_PLAT084_CUNY2021 ; PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.47 Report RESPONSE: electron diffraction data ; _vrf_PLAT183_CUNY2021 ; PROBLEM: Missing _cell_measurement_reflns_used Value .... Please Do ! RESPONSE: electron diffraction data ; _vrf_PLAT184_CUNY2021 ; PROBLEM: Missing _cell_measurement_theta_min Value ...... Please Do ! RESPONSE: electron diffraction data ; _vrf_PLAT185_CUNY2021 ; PROBLEM: Missing _cell_measurement_theta_max Value ...... Please Do ! RESPONSE: electron diffraction data ; # Added during the CSD deposition process: Thursday 21 April 2022 11:56 AM # end Validation Reply Form _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H16' _chemical_formula_weight 304.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.720(2) _cell_length_b 4.780(2) _cell_length_c 19.850(4) _cell_angle_alpha 90.00(3) _cell_angle_beta 92.22(3) _cell_angle_gamma 90.00(3) _cell_volume 731.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Micro/Nanocrystals _exptl_crystal_colour ? _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_F_000 137 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_absorpt_coefficient_mu 0.000 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.019687 _diffrn_radiation_type '300 keV electrons' _diffrn_source ? _diffrn_measurement_device_type Titan_Krios _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12893 _diffrn_reflns_av_unetI/netI 0.2345 _diffrn_reflns_av_R_equivalents 0.3186 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.040 _diffrn_reflns_theta_max 38.509 _diffrn_reflns_theta_full 36.870 _diffrn_measured_fraction_theta_max 0.908 _diffrn_measured_fraction_theta_full 0.947 _diffrn_reflns_Laue_measured_fraction_max 0.908 _diffrn_reflns_Laue_measured_fraction_full 0.947 _diffrn_reflns_point_group_measured_fraction_max 0.908 _diffrn_reflns_point_group_measured_fraction_full 0.947 _reflns_number_total 1348 _reflns_number_gt 750 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 1348 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2738 _refine_ls_R_factor_gt 0.2174 _refine_ls_wR_factor_ref 0.4720 _refine_ls_wR_factor_gt 0.4281 _refine_ls_goodness_of_fit_ref 1.376 _refine_ls_restrained_S_all 1.376 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.6381(10) 0.4094(13) 0.3033(5) 0.056(3) Uani 1 1 d . . . . . H1 H 0.743(6) 0.475(9) 0.262(3) 0.084 Uiso 1 1 d . U . . . C2 C 0.0699(9) 0.4971(13) 0.3911(5) 0.052(3) Uani 1 1 d . . . . . C3 C 0.5481(9) 0.1311(12) 0.3940(4) 0.042(2) Uani 1 1 d . . . . . C4 C 0.3653(7) -0.0401(11) 0.4803(4) 0.040(2) Uani 1 1 d . . . . . H2 H 0.302418 -0.217164 0.484159 0.049 Uiso 1 1 calc R U . . . C5 C 0.6750(10) 0.2019(14) 0.3522(5) 0.052(3) Uani 1 1 d . . . . . H3 H 0.800(6) 0.104(10) 0.358(3) 0.078 Uiso 1 1 d . U . . . C6 C 0.1802(10) 0.5876(13) 0.3442(5) 0.051(3) Uani 1 1 d . . . . . H4 H 0.124(7) 0.733(9) 0.302(3) 0.077 Uiso 1 1 d . U . . . C7 C 0.2750(8) 0.1723(12) 0.4371(5) 0.042(2) Uani 1 1 d . . . . . C8 C 0.3906(9) 0.2666(11) 0.3890(5) 0.046(2) Uani 1 1 d . . . . . C9 C 0.5525(8) -0.0702(10) 0.4519(4) 0.035(2) Uani 1 1 d . . . . . H5 H 0.585397 -0.261740 0.440332 0.042 Uiso 1 1 calc R U . . . C10 C 0.3472(10) 0.4709(13) 0.3414(5) 0.055(3) Uani 1 1 d . . . . . C11 C 0.4813(11) 0.5417(14) 0.2978(5) 0.060(3) Uani 1 1 d . . . . . H6 H 0.463(7) 0.696(12) 0.260(4) 0.090 Uiso 1 1 d . U . . . C12 C 0.1146(9) 0.2886(12) 0.4372(5) 0.049(3) Uani 1 1 d . . . . . H7 H 0.004(6) 0.235(8) 0.478(3) 0.074 Uiso 1 1 d . U . . . H8 H -0.063(8) 0.603(11) 0.386(4) 0.097(15) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.065(5) 0.035(3) 0.070(8) 0.006(4) 0.032(5) -0.001(3) C2 0.048(4) 0.038(3) 0.069(8) 0.008(4) 0.005(5) -0.005(3) C3 0.050(4) 0.030(3) 0.048(7) 0.002(3) 0.013(4) 0.001(3) C4 0.034(3) 0.029(3) 0.059(7) 0.010(3) 0.009(4) -0.001(2) C5 0.054(5) 0.047(3) 0.059(7) -0.007(4) 0.033(5) -0.011(3) C6 0.052(4) 0.039(3) 0.062(8) 0.004(4) 0.000(5) 0.003(3) C7 0.039(4) 0.034(3) 0.055(7) 0.005(3) 0.015(4) 0.001(3) C8 0.042(4) 0.030(3) 0.067(7) -0.004(3) 0.013(4) 0.001(2) C9 0.048(4) 0.022(2) 0.034(6) 0.005(3) 0.002(4) 0.001(2) C10 0.063(5) 0.032(3) 0.070(8) 0.007(3) 0.021(5) 0.000(3) C11 0.077(6) 0.032(3) 0.073(8) 0.004(4) 0.027(5) -0.004(3) C12 0.044(4) 0.033(3) 0.072(8) -0.001(3) 0.009(5) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C11 1.367(11) . ? C1 C5 1.409(12) . ? C2 C6 1.357(11) . ? C2 C12 1.387(11) . ? C3 C5 1.351(9) . ? C3 C8 1.378(9) . ? C3 C9 1.499(10) . ? C4 C7 1.486(10) . ? C4 C9 1.557(11) 3_656 ? C4 C9 1.578(8) . ? C6 C10 1.408(10) . ? C7 C12 1.357(9) . ? C7 C8 1.406(9) . ? C8 C10 1.390(12) . ? C10 C11 1.417(11) . ? 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 C11 C1 C5 122.4(7) . . ? C6 C2 C12 122.3(6) . . ? C5 C3 C8 119.8(8) . . ? C5 C3 C9 129.5(7) . . ? C8 C3 C9 110.5(6) . . ? C7 C4 C9 115.7(5) . 3_656 ? C7 C4 C9 105.8(5) . . ? C9 C4 C9 89.5(5) 3_656 . ? C3 C5 C1 117.8(7) . . ? C2 C6 C10 120.0(8) . . ? C12 C7 C8 118.2(8) . . ? C12 C7 C4 133.4(6) . . ? C8 C7 C4 108.4(5) . . ? C3 C8 C10 124.6(7) . . ? C3 C8 C7 112.5(8) . . ? C10 C8 C7 123.0(7) . . ? C3 C9 C4 116.2(5) . 3_656 ? C3 C9 C4 102.8(5) . . ? C4 C9 C4 90.5(5) 3_656 . ? C8 C10 C6 116.7(7) . . ? C8 C10 C11 114.9(7) . . ? C6 C10 C11 128.4(9) . . ? C1 C11 C10 120.4(9) . . ? C7 C12 C2 119.8(7) . . ? _refine_diff_density_max 0.256 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.074 _shelx_res_file ; TITL allmerge_a.res in P2(1)/n CUNY2021.res created by SHELXL-2018/3 at 19:03:13 on 09-Feb-2022 REM Old TITL all merge REM SHELXT solution in P2(1)/n: R1 0.449, Rweak 0.467, Alpha 0.156 REM 0.946 for 141 systematic absences, Orientation as input REM Formula found by SHELXT: C11 N CELL 1.00000 7.7200 4.7800 19.8500 90.000 92.219 90.000 ZERR 1.000 0.0020 0.0020 0.0040 0.030 0.030 0.030 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC H 0.042 0.991 0.103 3.924 0.205 11.597 0.170 31.984 0.006 = 0.0 0.0 0.000 0.310 1.008 SFAC C 0.208 0.922 0.702 5.018 1.144 16.523 0.425 47.300 0.030 = 0.0 0.0 0.000 0.770 12.011 UNIT 32 48 L.S. 50 ACTA BOND LIST 6 FMAP 2 PLAN 20 WGHT 0.200000 FVAR 27.17382 C1 2 0.638134 0.409442 0.303335 11.00000 0.06501 0.03527 = 0.06996 0.00613 0.03176 -0.00133 H1 1 0.743448 0.475187 0.261834 11.00000 -1.50000 C2 2 0.069892 0.497060 0.391140 11.00000 0.04818 0.03798 = 0.06863 0.00758 0.00495 -0.00501 C3 2 0.548096 0.131074 0.393975 11.00000 0.04974 0.02980 = 0.04757 0.00211 0.01282 0.00129 C4 2 0.365286 -0.040112 0.480339 11.00000 0.03412 0.02854 = 0.05927 0.00951 0.00860 -0.00062 AFIX 13 H2 1 0.302418 -0.217164 0.484159 11.00000 -1.20000 AFIX 0 C5 2 0.675019 0.201870 0.352173 11.00000 0.05371 0.04666 = 0.05905 -0.00652 0.03347 -0.01138 H3 1 0.799580 0.103643 0.358367 11.00000 -1.50000 C6 2 0.180153 0.587637 0.344215 11.00000 0.05229 0.03910 = 0.06191 0.00436 -0.00002 0.00254 H4 1 0.124275 0.733061 0.301610 11.00000 -1.50000 C7 2 0.274963 0.172305 0.437123 11.00000 0.03939 0.03421 = 0.05463 0.00457 0.01463 0.00071 C8 2 0.390551 0.266647 0.389003 11.00000 0.04239 0.03013 = 0.06689 -0.00434 0.01281 0.00124 C9 2 0.552485 -0.070169 0.451908 11.00000 0.04845 0.02212 = 0.03436 0.00464 0.00238 0.00082 AFIX 13 H5 1 0.585397 -0.261740 0.440332 11.00000 -1.20000 AFIX 0 C10 2 0.347192 0.470933 0.341446 11.00000 0.06345 0.03223 = 0.06995 0.00696 0.02059 -0.00035 C11 2 0.481311 0.541722 0.297781 11.00000 0.07712 0.03202 = 0.07314 0.00358 0.02667 -0.00357 H6 1 0.462873 0.695934 0.259628 11.00000 -1.50000 C12 2 0.114617 0.288593 0.437207 11.00000 0.04367 0.03334 = 0.07152 -0.00085 0.00928 -0.00371 H7 1 0.004302 0.234696 0.477949 11.00000 -1.50000 H8 1 -0.062574 0.602550 0.385853 11.00000 0.09656 HKLF 4 REM allmerge_a.res in P2(1)/n REM wR2 = 0.4720, GooF = S = 1.376, Restrained GooF = 1.376 for all data REM R1 = 0.2174 for 750 Fo > 4sig(Fo) and 0.2738 for all 1348 data REM 128 parameters refined using 0 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.256, deepest hole -0.241, 1-sigma level 0.074 Q1 1 0.3827 -0.4790 0.5002 11.00000 0.05 0.26 Q2 1 0.3999 0.9889 0.2818 11.00000 0.05 0.23 Q3 1 0.3226 -0.0145 0.3202 11.00000 0.05 0.21 Q4 1 0.1610 0.8998 0.3412 11.00000 0.05 0.21 Q5 1 0.0520 0.8627 0.3822 11.00000 0.05 0.21 Q6 1 0.3797 0.7602 0.3723 11.00000 0.05 0.19 Q7 1 0.3080 0.4545 0.4748 11.00000 0.05 0.19 Q8 1 0.5622 -0.5325 0.4224 11.00000 0.05 0.18 Q9 1 0.3890 -0.0574 0.3949 11.00000 0.05 0.17 Q10 1 0.6239 0.7682 0.3227 11.00000 0.05 0.17 Q11 1 0.2062 1.0189 0.2979 11.00000 0.05 0.17 Q12 1 0.6529 -0.0590 0.3377 11.00000 0.05 0.15 Q13 1 0.1121 0.2381 0.4053 11.00000 0.05 0.14 Q14 1 -0.1355 0.0658 0.4968 11.00000 0.05 0.13 Q15 1 0.3606 0.1480 0.3559 11.00000 0.05 0.13 Q16 1 0.8778 0.5381 0.2403 11.00000 0.05 0.12 Q17 1 0.6654 -0.3448 0.4338 11.00000 0.05 0.12 Q18 1 -0.1406 0.7832 0.4163 11.00000 0.05 0.12 Q19 1 0.6146 -0.3727 0.4432 11.00000 0.05 0.12 Q20 1 0.4926 0.1518 0.2975 11.00000 0.05 0.12 ; _shelx_res_checksum 97906