#------------------------------------------------------------------------------ #$Date: 2019-10-08 10:00:35 +0300 (Tue, 08 Oct 2019) $ #$Revision: 219153 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234454.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_7234454 loop_ _publ_author_name 'F. Grepioni' 'S. d'Agostino' 'D. Braga' 'A. Bertocco' 'L. Catalano' 'B. Ventura' _publ_section_title ; Fluorescent crystals and co-crystals of 1,8-naphthalimide derivatives: synthesis, structure determination and photophysical characterization ; _journal_name_full 'Journal of Materials Chemistry C' _journal_page_first 9425 _journal_page_last 9434 _journal_paper_doi 10.1039/C5TC01518A _journal_volume 3 _journal_year 2015 _chemical_formula_moiety 'C23 H21 N3 O2' _chemical_formula_sum 'C23 H21 N3 O2' _chemical_formula_weight 371.43 _space_group_IT_number 14 _space_group_name_Hall '-P 2yab' _space_group_name_H-M_alt 'P 1 21/a 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 93.08(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.4142(19) _cell_length_b 16.069(4) _cell_length_c 15.802(5) _cell_measurement_reflns_used 513 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.3978 _cell_measurement_theta_min 2.7457 _cell_volume 1879.9(9) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'Sir-92 (altomare, giacovazzo, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.1340 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.831 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 38.00 68.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 19.1580 179.0000 -150.0000 30 #__ type_ start__ end____ width___ exp.time_ 2 omega -26.00 88.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 19.1580 0.0000 -60.0000 114 #__ type_ start__ end____ width___ exp.time_ 3 omega 4.00 81.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 19.1580 38.0000 0.0000 77 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method 'omega scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0911 _diffrn_reflns_av_sigmaI/netI 0.2298 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 8601 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.46 _diffrn_reflns_theta_min 2.84 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92348 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.196 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.044 _refine_ls_extinction_coef 0.0012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 4343 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.2948 _refine_ls_R_factor_gt 0.1117 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0080P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0936 _refine_ls_wR_factor_ref 0.1365 _reflns_number_gt 1546 _reflns_number_total 4343 _reflns_threshold_expression >2\s(I) _cod_data_source_file J-Mater-Chem-C-2015-3-9425.cif _cod_data_source_block 4_2 _cod_original_cell_volume 1879.8(9) _cod_original_sg_symbol_H-M P21/a _cod_database_code 7234454 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0572(6) 0.0350(3) -0.1870(3) 0.0426(14) Uani 1 1 d . . . H1 H 0.0083 -0.0106 -0.2163 0.051 Uiso 1 1 calc R . . C2 C 0.1322(6) 0.0233(3) -0.1056(3) 0.0400(14) Uani 1 1 d . . . H2 H 0.1308 -0.0292 -0.0810 0.048 Uiso 1 1 calc R . . C3 C 0.2082(6) 0.0889(3) -0.0614(3) 0.0302(12) Uani 1 1 d . . . C4 C 0.1971(5) 0.1695(3) -0.0956(3) 0.0267(12) Uani 1 1 d . . . C5 C 0.1134(5) 0.1824(3) -0.1773(3) 0.0293(12) Uani 1 1 d . . . C6 C 0.0525(6) 0.1118(3) -0.2263(3) 0.0350(13) Uani 1 1 d . . . C7 C 0.0848(6) 0.2652(3) -0.2045(3) 0.0377(13) Uani 1 1 d . . . H7 H 0.0254 0.2751 -0.2569 0.045 Uiso 1 1 calc R . . C8 C 0.1426(6) 0.3314(3) -0.1555(3) 0.0366(13) Uani 1 1 d . . . H8 H 0.1202 0.3854 -0.1742 0.044 Uiso 1 1 calc R . . C9 C 0.2351(5) 0.3176(3) -0.0776(3) 0.0325(12) Uani 1 1 d . . . H9 H 0.2796 0.3625 -0.0457 0.039 Uiso 1 1 calc R . . C10 C 0.2607(6) 0.2382(3) -0.0478(3) 0.0279(12) Uani 1 1 d . . . C11 C 0.3022(6) 0.0746(3) 0.0216(3) 0.0377(13) Uani 1 1 d . . . C12 C 0.3611(6) 0.2265(3) 0.0351(3) 0.0319(12) Uani 1 1 d . . . C13 C 0.5023(6) 0.1288(3) 0.1372(3) 0.0453(14) Uani 1 1 d . . . H13A H 0.6009 0.1685 0.1375 0.054 Uiso 1 1 calc R . . H13B H 0.5540 0.0736 0.1326 0.054 Uiso 1 1 calc R . . C14 C 0.4142(7) 0.1349(3) 0.2200(3) 0.0373(13) Uani 1 1 d . . . C15 C 0.2423(7) 0.1628(3) 0.2296(3) 0.0482(15) Uani 1 1 d . . . H15 H 0.1694 0.1778 0.1823 0.058 Uiso 1 1 calc R . . C16 C 0.5143(8) 0.1144(4) 0.2932(4) 0.076(2) Uani 1 1 d . . . H16 H 0.6323 0.0955 0.2903 0.092 Uiso 1 1 calc R . . C17 C 0.4396(10) 0.1221(5) 0.3696(4) 0.099(3) Uani 1 1 d . . . H17 H 0.5095 0.1066 0.4177 0.119 Uiso 1 1 calc R . . C18 C 0.1771(8) 0.1689(3) 0.3098(4) 0.0697(19) Uani 1 1 d . . . H18 H 0.0591 0.1872 0.3145 0.084 Uiso 1 1 calc R . . C19 C -0.1306(6) 0.0592(3) -0.3478(3) 0.0557(16) Uani 1 1 d . . . H19A H -0.2142 0.0388 -0.3074 0.067 Uiso 1 1 calc R . . H19B H -0.0543 0.0131 -0.3632 0.067 Uiso 1 1 calc R . . C20 C -0.2359(7) 0.0915(3) -0.4267(3) 0.0655(18) Uani 1 1 d . . . H20A H -0.3210 0.1336 -0.4104 0.079 Uiso 1 1 calc R . . H20B H -0.3039 0.0462 -0.4535 0.079 Uiso 1 1 calc R . . C21 C -0.1088(8) 0.1286(3) -0.4896(3) 0.0724(19) Uani 1 1 d . . . H21A H -0.0367 0.0846 -0.5128 0.087 Uiso 1 1 calc R . . H21B H -0.1791 0.1544 -0.5360 0.087 Uiso 1 1 calc R . . C22 C 0.0148(7) 0.1929(3) -0.4468(3) 0.0588(16) Uani 1 1 d . . . H22A H 0.1027 0.2114 -0.4859 0.071 Uiso 1 1 calc R . . H22B H -0.0556 0.2407 -0.4309 0.071 Uiso 1 1 calc R . . C23 C 0.1118(6) 0.1561(3) -0.3683(3) 0.0510(15) Uani 1 1 d . . . H23A H 0.1890 0.1108 -0.3848 0.061 Uiso 1 1 calc R . . H23B H 0.1876 0.1983 -0.3406 0.061 Uiso 1 1 calc R . . N1 N 0.2734(8) 0.1501(4) 0.3804(3) 0.0855(19) Uani 1 1 d . . . N2 N 0.3826(5) 0.1441(2) 0.0618(2) 0.0312(10) Uani 1 1 d . . . N3 N -0.0192(5) 0.1250(2) -0.3088(2) 0.0415(11) Uani 1 1 d . . . O1 O 0.3141(5) 0.00678(18) 0.0558(2) 0.0590(11) Uani 1 1 d . . . O2 O 0.4238(4) 0.28242(18) 0.0780(2) 0.0436(10) 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 C1 0.054(4) 0.027(3) 0.047(4) -0.009(3) 0.004(3) -0.003(3) C2 0.050(4) 0.028(3) 0.044(4) 0.006(3) 0.014(3) 0.002(3) C3 0.034(3) 0.021(3) 0.036(3) 0.000(3) 0.007(2) 0.000(2) C4 0.023(3) 0.030(3) 0.027(3) -0.002(2) 0.006(2) 0.003(2) C5 0.024(3) 0.029(3) 0.035(3) -0.001(2) 0.005(2) -0.003(2) C6 0.027(3) 0.042(3) 0.037(3) -0.008(3) 0.005(2) -0.004(3) C7 0.044(3) 0.041(3) 0.028(3) 0.000(3) 0.006(3) 0.002(3) C8 0.040(3) 0.030(3) 0.040(4) 0.005(3) 0.008(3) 0.003(3) C9 0.032(3) 0.030(3) 0.036(3) -0.007(3) 0.002(2) -0.007(3) C10 0.030(3) 0.029(3) 0.025(3) -0.002(2) 0.009(2) 0.000(2) C11 0.037(3) 0.035(3) 0.042(4) 0.005(3) 0.004(3) 0.006(3) C12 0.026(3) 0.032(3) 0.038(3) 0.000(3) 0.007(2) -0.002(3) C13 0.034(3) 0.052(3) 0.050(4) 0.001(3) -0.002(3) 0.002(3) C14 0.042(3) 0.036(3) 0.034(3) 0.006(3) -0.005(3) -0.007(3) C15 0.062(4) 0.046(3) 0.038(4) 0.004(3) 0.012(3) 0.009(3) C16 0.066(4) 0.120(6) 0.040(4) 0.027(4) -0.012(4) -0.017(4) C17 0.086(6) 0.151(7) 0.058(5) 0.038(5) -0.031(5) -0.046(6) C18 0.083(5) 0.069(4) 0.059(5) -0.007(4) 0.023(4) -0.006(4) C19 0.061(4) 0.058(4) 0.048(4) -0.012(3) -0.003(3) -0.015(3) C20 0.080(5) 0.064(4) 0.051(4) -0.005(3) -0.017(4) -0.013(4) C21 0.099(5) 0.074(4) 0.042(4) -0.008(4) -0.009(4) -0.003(4) C22 0.072(4) 0.069(4) 0.037(4) -0.005(3) 0.011(3) -0.010(3) C23 0.055(4) 0.056(4) 0.043(4) -0.005(3) 0.006(3) -0.002(3) N1 0.106(5) 0.108(5) 0.043(4) -0.003(3) 0.007(4) -0.036(4) N2 0.031(2) 0.033(2) 0.029(2) -0.003(2) -0.0004(19) -0.002(2) N3 0.047(3) 0.048(3) 0.029(3) -0.005(2) 0.002(2) -0.014(2) O1 0.078(3) 0.035(2) 0.063(3) 0.018(2) -0.012(2) -0.004(2) O2 0.048(2) 0.036(2) 0.046(2) -0.0080(18) -0.0077(18) -0.0050(18) 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' O O 0.0106 0.0060 '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 C6 C1 C2 122.5(4) . . C3 C2 C1 120.2(4) . . C2 C3 C4 120.0(4) . . C2 C3 C11 119.9(4) . . C4 C3 C11 120.1(4) . . C10 C4 C3 120.5(4) . . C10 C4 C5 119.5(4) . . C3 C4 C5 119.9(4) . . C7 C5 C4 117.8(4) . . C7 C5 C6 122.9(4) . . C4 C5 C6 119.1(4) . . C1 C6 N3 123.7(4) . . C1 C6 C5 117.7(4) . . N3 C6 C5 118.5(4) . . C8 C7 C5 121.4(4) . . C7 C8 C9 120.0(4) . . C10 C9 C8 120.2(4) . . C9 C10 C4 120.8(4) . . C9 C10 C12 118.3(4) . . C4 C10 C12 120.9(4) . . O1 C11 N2 119.5(4) . . O1 C11 C3 123.7(5) . . N2 C11 C3 116.8(4) . . O2 C12 N2 120.3(5) . . O2 C12 C10 124.3(4) . . N2 C12 C10 115.5(4) . . N2 C13 C14 115.2(4) . . C15 C14 C16 116.6(5) . . C15 C14 C13 124.9(4) . . C16 C14 C13 118.5(5) . . C14 C15 C18 119.9(5) . . C17 C16 C14 119.8(6) . . N1 C17 C16 124.5(6) . . N1 C18 C15 123.7(6) . . N3 C19 C20 110.6(4) . . C19 C20 C21 111.0(4) . . C22 C21 C20 110.8(4) . . C23 C22 C21 110.3(4) . . N3 C23 C22 110.6(4) . . C18 N1 C17 115.5(6) . . C12 N2 C11 125.4(4) . . C12 N2 C13 117.3(4) . . C11 N2 C13 117.3(4) . . C6 N3 C19 117.5(4) . . C6 N3 C23 114.6(4) . . C19 N3 C23 110.7(4) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 C6 1.381(5) . C1 C2 1.386(5) . C2 C3 1.369(5) . C3 C4 1.405(5) . C3 C11 1.470(6) . C4 C10 1.404(5) . C4 C5 1.417(5) . C5 C7 1.411(5) . C5 C6 1.434(5) . C6 N3 1.397(5) . C7 C8 1.371(5) . C8 C9 1.394(5) . C9 C10 1.370(5) . C10 C12 1.484(5) . C11 O1 1.218(5) . C11 N2 1.401(5) . C12 O2 1.204(5) . C12 N2 1.396(5) . C13 N2 1.468(5) . C13 C14 1.497(6) . C14 C15 1.368(6) . C14 C16 1.380(6) . C15 C18 1.384(6) . C16 C17 1.360(7) . C17 N1 1.332(7) . C18 N1 1.326(6) . C19 N3 1.458(5) . C19 C20 1.526(5) . C20 C21 1.527(6) . C21 C22 1.516(6) . C22 C23 1.518(5) . C23 N3 1.475(5) .