#------------------------------------------------------------------------------ #$Date: 2020-05-04 12:32:27 +0300 (Mon, 04 May 2020) $ #$Revision: 251492 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126492.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_7126492 loop_ _publ_author_name 'Levine, Andrew M.' 'Bu, Guanhong' 'Biswas, Sankarsan' 'Tsai, Esther H. R.' 'Braunschweig, Adam B.' 'Nannenga, Brent L.' _publ_section_title ; Crystal structure and orientation of organic semiconductor thin films by microcrystal electron diffraction and grazing-incidence wide-angle X-ray scattering. ; _journal_issue 30 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 4204 _journal_page_last 4207 _journal_paper_doi 10.1039/d0cc00119h _journal_volume 56 _journal_year 2020 _chemical_formula_sum 'C32 H8 N8 O8 S0' _chemical_formula_weight 632.46 _chemical_name_common 'dCN NDI' _chemical_name_systematic 'dicyano naphthalene diimide' _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 difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-11-05 deposited with the CCDC. 2020-03-13 downloaded from the CCDC. ; _cell_angle_alpha 90.00(3) _cell_angle_beta 104.71(3) _cell_angle_gamma 90.00(3) _cell_formula_units_Z 1 _cell_length_a 8.090(2) _cell_length_b 6.390(2) _cell_length_c 11.630(2) _cell_measurement_temperature 77 _cell_volume 581.5(3) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 77 _diffrn_measured_fraction_theta_full 0.755 _diffrn_measured_fraction_theta_max 0.735 _diffrn_measurement_device_type Titan_Krios _diffrn_radiation_type electron _diffrn_radiation_wavelength 1.000 _diffrn_reflns_av_R_equivalents 0.1843 _diffrn_reflns_av_unetI/netI 0.0974 _diffrn_reflns_Laue_measured_fraction_full 0.755 _diffrn_reflns_Laue_measured_fraction_max 0.735 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 26791 _diffrn_reflns_point_group_measured_fraction_full 0.755 _diffrn_reflns_point_group_measured_fraction_max 0.735 _diffrn_reflns_theta_full 36.870 _diffrn_reflns_theta_max 61.207 _diffrn_reflns_theta_min 3.664 _exptl_absorpt_coefficient_mu 0.000 _exptl_crystal_density_diffrn 1.806 _exptl_crystal_description Micro/Nanocrystals _exptl_crystal_F_000 118 _refine_diff_density_max 0.187 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef 3.5(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 118 _refine_ls_number_reflns 2413 _refine_ls_number_restraints 81 _refine_ls_restrained_S_all 1.122 _refine_ls_R_factor_all 0.1690 _refine_ls_R_factor_gt 0.1376 _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^)+(0.1745P)^2^+0.0515P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3719 _refine_ls_wR_factor_ref 0.3919 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1654 _reflns_number_total 2413 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc00119h2.cif _cod_data_source_block dCN_NDI_merged_small_a _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7126492 _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. ; _shelx_res_file ; TITL dCN_NDI_merged_small_a.res in P2(1)/c dCN_NDI_merged_small_a.res created by SHELXL-2018/3 at 20:20:13 on 12-Sep-2019 REM Old TITL all merge REM SHELXT solution in P2(1)/c: R1 0.344, Rweak 0.609, Alpha 0.135 REM 3.801 for 55 systematic absences, Orientation as input REM Formula found by SHELXT: C9 N O2 CELL 1 8.0900 6.3900 11.6300 90.000 104.711 90.000 ZERR 1.000 0.0020 0.0020 0.0020 0.030 0.030 0.030 LATT 1 SYMM -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 SFAC N 0.216 0.843 0.649 4.055 0.968 12.693 0.345 36.058 0.032 = 0.0 0.0 0.000 0.700 14.007 SFAC O 0.308 1.088 0.733 4.593 0.710 13.052 0.185 33.768 0.048 = 0.0 0.0 0.000 0.660 15.999 SFAC S 0.610 1.173 1.367 6.371 2.268 18.858 0.808 49.703 0.108 = 0.0 0.0 0.000 1.030 32.060 UNIT 8 32 8 8 0 ACTA L.S. 100 BOND LIST 6 FMAP 2 PLAN 20 RIGU WGHT 0.174500 0.051500 EXTI 3.479617 FVAR 5.30649 O001 4 0.998412 0.346704 0.680539 11.00000 0.01216 0.02350 = 0.05253 0.00048 -0.00143 -0.00259 C002 2 0.846280 0.320796 0.648580 11.00000 0.01235 0.01657 = 0.04756 0.00522 -0.00044 -0.00222 O003 4 0.553761 -0.053771 0.698012 11.00000 0.01946 0.01966 = 0.05941 0.01223 0.00128 -0.00366 N4 3 0.772553 0.146806 0.682398 11.00000 0.01659 0.01921 = 0.05338 0.00157 0.00016 -0.00235 H4 1 0.852392 0.043759 0.735023 11.00000 0.03178 C005 2 0.794473 0.645737 0.530704 11.00000 0.01279 0.01495 = 0.05465 0.00235 0.00175 -0.00496 H5 1 0.938968 0.686617 0.560432 11.00000 0.04249 C006 2 0.602767 0.101248 0.659014 11.00000 0.01726 0.01639 = 0.04016 0.00319 0.00360 -0.00211 C007 2 0.685098 0.786623 0.454461 11.00000 0.01570 0.01256 = 0.04378 0.00046 0.00242 -0.00816 C008 2 0.730046 0.469692 0.570831 11.00000 0.01185 0.01595 = 0.04515 0.00262 0.00085 -0.00393 N009 3 0.838432 1.110131 0.403640 11.00000 0.02796 0.02556 = 0.06760 0.00831 0.00517 -0.01355 C00A 2 0.554173 0.429264 0.538133 11.00000 0.01327 0.01419 = 0.03944 0.00123 0.00212 -0.00139 C00B 2 0.487397 0.249309 0.579116 11.00000 0.01414 0.01408 = 0.04626 0.00054 0.00179 -0.00338 C00C 2 0.763013 0.967282 0.418870 11.00000 0.02292 0.01730 = 0.06744 0.00735 0.01022 -0.00288 HKLF 4 REM dCN_NDI_merged_small_a.res in P2(1)/c REM wR2 = 0.3919, GooF = S = 1.141, Restrained GooF = 1.122 for all data REM R1 = 0.1376 for 1654 Fo > 4sig(Fo) and 0.1690 for all 2413 data REM 118 parameters refined using 81 restraints END WGHT 0.1617 0.0460 REM Highest difference peak 0.187, deepest hole -0.194, 1-sigma level 0.049 Q1 1 0.5314 0.4807 0.5844 11.00000 0.05 0.19 Q2 1 0.6910 0.9678 0.4596 11.00000 0.05 0.16 Q3 1 0.5626 -0.0253 0.6228 11.00000 0.05 0.14 Q4 1 0.8525 0.0322 0.8662 11.00000 0.05 0.14 Q5 1 0.4234 0.3194 0.4738 11.00000 0.05 0.14 Q6 1 0.8695 0.7576 0.4584 11.00000 0.05 0.13 Q7 1 0.6415 0.5107 0.4742 11.00000 0.05 0.13 Q8 1 0.8600 0.2645 0.6199 11.00000 0.05 0.13 Q9 1 0.9040 1.2046 0.4445 11.00000 0.05 0.13 Q10 1 0.5687 0.1389 0.6948 11.00000 0.05 0.12 Q11 1 0.8435 0.3544 0.7306 11.00000 0.05 0.12 Q12 1 0.9409 0.6565 0.5076 11.00000 0.05 0.12 Q13 1 0.7150 0.4462 0.5042 11.00000 0.05 0.12 Q14 1 0.8812 1.0199 0.5539 11.00000 0.05 0.12 Q15 1 0.7002 1.2608 0.3948 11.00000 0.05 0.11 Q16 1 0.7995 0.6951 0.6013 11.00000 0.05 0.11 Q17 1 0.8641 0.2445 0.7933 11.00000 0.05 0.11 Q18 1 0.7374 0.1870 0.7437 11.00000 0.05 0.11 Q19 1 0.5269 0.3834 0.4019 11.00000 0.05 0.11 Q20 1 0.6739 -0.0371 0.6629 11.00000 0.05 0.11 ; _shelx_res_checksum 3123 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 O001 O 0.9984(3) 0.3467(4) 0.6805(4) 0.0311(10) Uani 1 1 d . . . . . C002 C 0.8463(4) 0.3208(4) 0.6486(4) 0.0270(11) Uani 1 1 d . . . . . O003 O 0.5538(3) -0.0538(4) 0.6980(4) 0.0344(10) Uani 1 1 d . . . . . N4 N 0.7726(3) 0.1468(4) 0.6824(4) 0.0313(11) Uani 1 1 d . . . . . H4 H 0.852(2) 0.044(3) 0.735(2) 0.032(4) Uiso 1 1 d . . . . . C005 C 0.7945(4) 0.6457(4) 0.5307(5) 0.0287(11) Uani 1 1 d . . . . . H5 H 0.939(3) 0.687(3) 0.560(3) 0.042(5) Uiso 1 1 d . . . . . C006 C 0.6028(4) 0.1012(5) 0.6590(4) 0.0253(11) Uani 1 1 d . . . . . C007 C 0.6851(4) 0.7866(4) 0.4545(4) 0.0249(10) Uani 1 1 d . . . . . C008 C 0.7300(4) 0.4697(4) 0.5708(4) 0.0255(10) Uani 1 1 d . . . . . N009 N 0.8384(4) 1.1101(5) 0.4036(5) 0.0416(14) Uani 1 1 d . . . . . C00A C 0.5542(3) 0.4293(4) 0.5381(4) 0.0231(10) Uani 1 1 d . . . . . C00B C 0.4874(4) 0.2493(4) 0.5791(4) 0.0259(11) Uani 1 1 d . . . . . C00C C 0.7630(4) 0.9673(5) 0.4189(5) 0.0361(13) 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 O001 0.0122(9) 0.0235(11) 0.053(3) 0.0005(11) -0.0014(10) -0.0026(7) C002 0.0124(11) 0.0166(12) 0.048(3) 0.0052(13) -0.0004(13) -0.0022(8) O003 0.0195(10) 0.0197(10) 0.059(3) 0.0122(12) 0.0013(12) -0.0037(8) N4 0.0166(10) 0.0192(11) 0.053(3) 0.0016(12) 0.0002(12) -0.0024(8) C005 0.0128(11) 0.0149(12) 0.055(4) 0.0024(13) 0.0018(13) -0.0050(8) C006 0.0173(12) 0.0164(12) 0.040(3) 0.0032(12) 0.0036(13) -0.0021(9) C007 0.0157(11) 0.0126(11) 0.044(3) 0.0005(12) 0.0024(13) -0.0082(8) C008 0.0119(10) 0.0159(12) 0.045(3) 0.0026(12) 0.0009(12) -0.0039(8) N009 0.0280(14) 0.0256(14) 0.068(4) 0.0083(16) 0.0052(16) -0.0136(11) C00A 0.0133(10) 0.0142(11) 0.039(3) 0.0012(12) 0.0021(12) -0.0014(8) C00B 0.0141(11) 0.0141(11) 0.046(3) 0.0005(12) 0.0018(13) -0.0034(8) C00C 0.0229(14) 0.0173(13) 0.067(4) 0.0074(16) 0.0102(17) -0.0029(10) 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' N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.0000 0.0000 '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 O001 C002 N4 120.7(3) . . ? O001 C002 C008 122.9(3) . . ? N4 C002 C008 116.4(3) . . ? C006 N4 C002 127.5(3) . . ? C008 C005 C007 120.5(3) . . ? O003 C006 N4 121.0(3) . . ? O003 C006 C00B 123.4(3) . . ? N4 C006 C00B 115.6(3) . . ? C00B C007 C005 120.3(3) 3_666 . ? C00B C007 C00C 123.1(3) 3_666 . ? C005 C007 C00C 116.6(3) . . ? C005 C008 C00A 120.5(3) . . ? C005 C008 C002 120.0(3) . . ? C00A C008 C002 119.5(3) . . ? C008 C00A C00B 120.7(3) . . ? C008 C00A C00A 118.7(4) . 3_666 ? C00B C00A C00A 120.6(3) . 3_666 ? C007 C00B C00A 119.5(3) 3_666 . ? C007 C00B C006 120.4(3) 3_666 . ? C00A C00B C006 120.1(3) . . ? N009 C00C C007 171.8(5) . . ? 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 O001 C002 1.203(4) . ? C002 N4 1.366(4) . ? C002 C008 1.475(5) . ? O003 C006 1.198(4) . ? N4 C006 1.362(4) . ? C005 C008 1.371(5) . ? C005 C007 1.408(5) . ? C006 C00B 1.480(5) . ? C007 C00B 1.370(4) 3_666 ? C007 C00C 1.426(5) . ? C008 C00A 1.400(4) . ? N009 C00C 1.137(4) . ? C00A C00B 1.404(5) . ? C00A C00A 1.406(6) 3_666 ?