#------------------------------------------------------------------------------ #$Date: 2019-10-11 11:06:48 +0300 (Fri, 11 Oct 2019) $ #$Revision: 219284 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/45/7234548.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_7234548 loop_ _publ_author_name 'Martin Ipuy' 'Yuan-Yuan Liao' 'Erwann Jeanneau' 'Patrice L. Baldeck' 'Yann Bretonniere' 'Chantal Andraud' _publ_section_title ; Solid state red biphotonic excited emission from small dipolar fluorophores ; _journal_name_full 'Journal of Materials Chemistry C' _journal_page_first 766 _journal_page_last 779 _journal_paper_doi 10.1039/C5TC03465E _journal_volume 4 _journal_year 2016 _chemical_absolute_configuration . _chemical_formula_moiety 'C20 H17 N3 O3' _chemical_formula_sum 'C20 H17 N3 O3' _chemical_formula_weight 347.37 _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _cell_angle_alpha 90 _cell_angle_beta 94.990(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.397(2) _cell_length_b 9.8280(10) _cell_length_c 17.179(2) _cell_measurement_reflns_used 4290 _cell_measurement_temperature 150 _cell_measurement_theta_max 66.8020 _cell_measurement_theta_min 4.1730 _cell_volume 1748.7(4) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 150 _diffrn_detector_area_resol_mean 10.4678 _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method \w _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.091 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 13075 _diffrn_reflns_theta_full 67.676 _diffrn_reflns_theta_max 67.856 _diffrn_reflns_theta_min 4.268 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.741 _exptl_absorpt_correction_T_max 0.946 _exptl_absorpt_correction_T_min 0.824 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 728 _exptl_crystal_preparation Luminescent _exptl_crystal_size_max 0.456 _exptl_crystal_size_mid 0.125 _exptl_crystal_size_min 0.084 _refine_diff_density_max 0.33 _refine_diff_density_min -0.42 _refine_ls_extinction_coef 36(4) _refine_ls_extinction_method 'Larson (1970), Equation 22' _refine_ls_goodness_of_fit_ref 0.9987 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3091 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0837 _refine_ls_R_factor_gt 0.0661 _refine_ls_shift/su_max 0.0001793 _refine_ls_shift/su_mean 0.0000250 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.274E+04 0.457E+04 0.276E+04 0.109E+04 220. ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.2043 _refine_ls_wR_factor_gt 0.1605 _refine_ls_wR_factor_ref 0.2043 _reflns_limit_h_max 12 _reflns_limit_h_min -12 _reflns_limit_k_max 11 _reflns_limit_k_min 0 _reflns_limit_l_max 20 _reflns_limit_l_min 0 _reflns_number_gt 2401 _reflns_number_total 3103 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 3.46 _oxford_diffrn_Wilson_scale 0.03 _oxford_refine_ls_r_factor_ref 0.0837 _oxford_refine_ls_scale 5.7(3) _oxford_reflns_number_all 3091 _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _cod_data_source_file J-Mater-Chem-C-2016-4-766.cif _cod_data_source_block 4 _cod_original_sg_symbol_H-M 'P 1 21/c 1 ' _cod_database_code 7234548 _iucr_refine_instruction_details_constraints ; # # Punched on 22/11/13 at 14:37:36 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) H ( 83,X'S) RIDE C ( 9,X'S) H ( 91,X'S) H ( 92,X'S) H ( 93,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 152,X'S) H ( 153,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 21,X'S) H ( 212,X'S) H ( 213,X'S) H ( 211,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 22/11/13 at 14:37:36 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.40874(19) 0.2726(2) 0.33411(10) 0.0397 1.0000 Uani . . . . . . C2 C 0.3831(2) 0.3286(3) 0.40173(15) 0.0353 1.0000 Uani . . . . . . C3 C 0.4652(3) 0.2702(3) 0.46434(15) 0.0354 1.0000 Uani . . . . . . C4 C 0.4664(3) 0.3022(3) 0.54541(16) 0.0392 1.0000 Uani . . . . . . N5 N 0.4730(3) 0.3244(3) 0.61074(15) 0.0567 1.0000 Uani . . . . . . C6 C 0.5468(3) 0.1784(3) 0.43435(15) 0.0358 1.0000 Uani . . . . . . C7 C 0.5190(3) 0.1779(3) 0.34648(15) 0.0361 1.0000 Uani . . . . . . C8 C 0.6285(3) 0.2406(3) 0.30571(16) 0.0406 1.0000 Uani . . . . . . H81 H 0.7025 0.1813 0.3099 0.0617 1.0000 Uiso R . . . . . H82 H 0.6011 0.2521 0.2502 0.0614 1.0000 Uiso R . . . . . H83 H 0.6520 0.3284 0.3284 0.0619 1.0000 Uiso R . . . . . C9 C 0.4721(3) 0.0431(3) 0.31137(16) 0.0423 1.0000 Uani . . . . . . H91 H 0.5428 -0.0220 0.3153 0.0634 1.0000 Uiso R . . . . . H92 H 0.4408 0.0573 0.2577 0.0636 1.0000 Uiso R . . . . . H93 H 0.4024 0.0092 0.3405 0.0634 1.0000 Uiso R . . . . . C10 C 0.6437(3) 0.1047(3) 0.48061(16) 0.0391 1.0000 Uani . . . . . . C11 C 0.7215(3) 0.0094(3) 0.45265(16) 0.0382 1.0000 Uani . . . . . . C12 C 0.8197(3) -0.0723(3) 0.49546(15) 0.0363 1.0000 Uani . . . . . . C13 C 0.8688(3) -0.0509(3) 0.57333(16) 0.0382 1.0000 Uani . . . . . . O14 O 0.81975(19) 0.0586(2) 0.60975(11) 0.0430 1.0000 Uani . . . . . . C15 C 0.8727(3) 0.0923(3) 0.68625(17) 0.0470 1.0000 Uani . . . . . . H151 H 0.8341 0.1776 0.7006 0.0717 1.0000 Uiso R . . . . . H152 H 0.8519 0.0213 0.7217 0.0719 1.0000 Uiso R . . . . . H153 H 0.9653 0.1005 0.6859 0.0719 1.0000 Uiso R . . . . . C16 C 0.9631(3) -0.1351(3) 0.60964(18) 0.0450 1.0000 Uani . . . . . . C17 C 1.0090(3) -0.2422(3) 0.56766(19) 0.0481 1.0000 Uani . . . . . . C18 C 0.9645(3) -0.2667(3) 0.49104(19) 0.0456 1.0000 Uani . . . . . . C19 C 0.8712(3) -0.1827(3) 0.45486(17) 0.0414 1.0000 Uani . . . . . . O20 O 0.8222(2) -0.1962(2) 0.37906(12) 0.0494 1.0000 Uani . . . . . . C21 C 0.8514(4) -0.3152(3) 0.33745(19) 0.0545 1.0000 Uani . . . . . . H212 H 0.8066 -0.3100 0.2852 0.0815 1.0000 Uiso R . . . . . H213 H 0.8218 -0.3956 0.3646 0.0813 1.0000 Uiso R . . . . . H211 H 0.9439 -0.3213 0.3346 0.0819 1.0000 Uiso R . . . . . H181 H 0.9975 -0.3394 0.4640 0.0560 1.0000 Uiso R . . . . . H171 H 1.0723 -0.3000 0.5924 0.0573 1.0000 Uiso R . . . . . H161 H 0.9954 -0.1180 0.6614 0.0542 1.0000 Uiso R . . . . . H111 H 0.7101 -0.0055 0.3981 0.0469 1.0000 Uiso R . . . . . H101 H 0.6512 0.1251 0.5340 0.0467 1.0000 Uiso R . . . . . C22 C 0.2916(3) 0.4276(3) 0.40347(15) 0.0375 1.0000 Uani . . . . . . C23 C 0.2196(3) 0.4732(3) 0.33414(17) 0.0410 1.0000 Uani . . . . . . N24 N 0.1599(3) 0.5140(3) 0.28017(17) 0.0559 1.0000 Uani . . . . . . C25 C 0.2687(3) 0.4955(3) 0.47377(17) 0.0402 1.0000 Uani . . . . . . N26 N 0.2507(3) 0.5549(3) 0.52974(16) 0.0515 1.0000 Uani . . . . . . 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 O1 0.0431(11) 0.0470(11) 0.0293(10) -0.0012(7) 0.0047(8) 0.0080(8) C2 0.0350(13) 0.0372(14) 0.0344(13) -0.0016(10) 0.0074(10) 0.0002(10) C3 0.0381(14) 0.0376(14) 0.0312(13) 0.0007(10) 0.0067(10) 0.0016(10) C4 0.0416(15) 0.0437(14) 0.0331(15) 0.0010(11) 0.0077(11) 0.0078(11) N5 0.0651(18) 0.0698(19) 0.0356(14) -0.0024(12) 0.0069(12) 0.0121(14) C6 0.0384(14) 0.0370(14) 0.0327(13) 0.0026(10) 0.0073(10) 0.0028(11) C7 0.0391(14) 0.0386(14) 0.0315(13) -0.0019(10) 0.0077(10) 0.0061(11) C8 0.0415(15) 0.0447(16) 0.0364(14) 0.0024(11) 0.0083(11) 0.0006(11) C9 0.0447(15) 0.0421(15) 0.0400(15) -0.0002(12) 0.0033(12) -0.0024(12) C10 0.0387(14) 0.0443(16) 0.0349(14) 0.0041(11) 0.0071(11) 0.0050(11) C11 0.0395(14) 0.0385(14) 0.0375(13) 0.0031(11) 0.0081(11) 0.0034(11) C12 0.0340(13) 0.0378(14) 0.0385(14) 0.0007(11) 0.0112(11) 0.0006(10) C13 0.0381(13) 0.0357(13) 0.0421(14) 0.0027(11) 0.0104(11) 0.0033(11) O14 0.0430(11) 0.0482(12) 0.0383(10) -0.0019(8) 0.0056(8) 0.0100(8) C15 0.0458(16) 0.0500(17) 0.0451(16) -0.0021(13) 0.0035(12) 0.0027(13) C16 0.0424(15) 0.0437(16) 0.0488(16) 0.0025(12) 0.0040(12) 0.0030(12) C17 0.0425(16) 0.0438(16) 0.0581(19) 0.0033(13) 0.0042(13) 0.0071(12) C18 0.0439(16) 0.0378(15) 0.0565(18) -0.0010(13) 0.0114(13) 0.0062(12) C19 0.0415(15) 0.0389(15) 0.0450(15) 0.0005(11) 0.0109(12) 0.0021(11) O20 0.0584(13) 0.0479(12) 0.0429(11) -0.0046(9) 0.0091(9) 0.0130(10) C21 0.069(2) 0.0453(18) 0.0514(18) -0.0087(14) 0.0175(15) 0.0067(15) C22 0.0373(14) 0.0380(14) 0.0376(14) 0.0000(11) 0.0051(11) 0.0017(11) C23 0.0399(14) 0.0397(15) 0.0436(15) 0.0007(12) 0.0047(12) 0.0030(11) N24 0.0561(16) 0.0570(17) 0.0533(16) 0.0041(13) -0.0031(13) 0.0061(13) C25 0.0369(14) 0.0388(15) 0.0456(16) 0.0011(12) 0.0069(11) 0.0057(11) N26 0.0535(15) 0.0480(15) 0.0542(16) -0.0062(12) 0.0111(12) 0.0080(12) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C7 . 110.28(19) yes O1 . C2 . C3 . 109.7(2) yes O1 . C2 . C22 . 120.5(2) yes C3 . C2 . C22 . 129.9(2) yes C2 . C3 . C4 . 126.7(2) yes C2 . C3 . C6 . 109.2(2) yes C4 . C3 . C6 . 124.0(3) yes C3 . C4 . N5 . 176.6(3) yes C3 . C6 . C7 . 107.9(2) yes C3 . C6 . C10 . 123.8(2) yes C7 . C6 . C10 . 128.3(2) yes C6 . C7 . O1 . 102.71(19) yes C6 . C7 . C8 . 111.9(2) yes O1 . C7 . C8 . 106.3(2) yes C6 . C7 . C9 . 115.3(2) yes O1 . C7 . C9 . 105.9(2) yes C8 . C7 . C9 . 113.5(2) yes C7 . C8 . H81 . 110.3 no C7 . C8 . H82 . 109.3 no H81 . C8 . H82 . 107.8 no C7 . C8 . H83 . 110.4 no H81 . C8 . H83 . 109.7 no H82 . C8 . H83 . 109.4 no C7 . C9 . H91 . 109.4 no C7 . C9 . H92 . 109.0 no H91 . C9 . H92 . 110.7 no C7 . C9 . H93 . 108.7 no H91 . C9 . H93 . 109.3 no H92 . C9 . H93 . 109.7 no C6 . C10 . C11 . 124.7(3) yes C6 . C10 . H101 . 115.6 no C11 . C10 . H101 . 119.7 no C10 . C11 . C12 . 128.3(3) yes C10 . C11 . H111 . 115.6 no C12 . C11 . H111 . 116.1 no C11 . C12 . C13 . 125.6(2) yes C11 . C12 . C19 . 117.0(3) yes C13 . C12 . C19 . 117.4(3) yes C12 . C13 . O14 . 115.8(2) yes C12 . C13 . C16 . 121.5(3) yes O14 . C13 . C16 . 122.7(3) yes C13 . O14 . C15 . 118.6(2) yes O14 . C15 . H151 . 107.6 no O14 . C15 . H152 . 109.1 no H151 . C15 . H152 . 110.1 no O14 . C15 . H153 . 108.6 no H151 . C15 . H153 . 111.3 no H152 . C15 . H153 . 110.1 no C13 . C16 . C17 . 118.7(3) yes C13 . C16 . H161 . 120.0 no C17 . C16 . H161 . 121.3 no C16 . C17 . C18 . 121.9(3) yes C16 . C17 . H171 . 118.9 no C18 . C17 . H171 . 119.2 no C17 . C18 . C19 . 119.4(3) yes C17 . C18 . H181 . 120.1 no C19 . C18 . H181 . 120.6 no C12 . C19 . C18 . 121.1(3) yes C12 . C19 . O20 . 114.7(3) yes C18 . C19 . O20 . 124.2(3) yes C19 . O20 . C21 . 118.9(3) yes O20 . C21 . H212 . 108.3 no O20 . C21 . H213 . 109.6 no H212 . C21 . H213 . 109.6 no O20 . C21 . H211 . 109.5 no H212 . C21 . H211 . 110.7 no H213 . C21 . H211 . 109.1 no C2 . C22 . C23 . 121.6(2) yes C2 . C22 . C25 . 121.6(2) yes C23 . C22 . C25 . 116.7(2) yes C22 . C23 . N24 . 177.3(3) yes C22 . C25 . N26 . 177.7(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.333(3) yes O1 . C7 . 1.477(3) yes C2 . C3 . 1.434(4) yes C2 . C22 . 1.362(4) yes C3 . C4 . 1.427(4) yes C3 . C6 . 1.370(4) yes C4 . N5 . 1.139(4) yes C6 . C7 . 1.512(4) yes C6 . C10 . 1.426(4) yes C7 . C8 . 1.518(4) yes C7 . C9 . 1.518(4) yes C8 . H81 . 0.963 no C8 . H82 . 0.978 no C8 . H83 . 0.970 no C9 . H91 . 0.972 no C9 . H92 . 0.961 no C9 . H93 . 0.975 no C10 . C11 . 1.352(4) yes C10 . H101 . 0.936 no C11 . C12 . 1.448(4) yes C11 . H111 . 0.946 no C12 . C13 . 1.406(4) yes C12 . C19 . 1.419(4) yes C13 . O14 . 1.365(3) yes C13 . C16 . 1.389(4) yes O14 . C15 . 1.419(3) yes C15 . H151 . 0.971 no C15 . H152 . 0.963 no C15 . H153 . 0.966 no C16 . C17 . 1.384(4) yes C16 . H161 . 0.939 no C17 . C18 . 1.378(5) yes C17 . H171 . 0.943 no C18 . C19 . 1.380(4) yes C18 . H181 . 0.934 no C19 . O20 . 1.363(4) yes O20 . C21 . 1.418(4) yes C21 . H212 . 0.976 no C21 . H213 . 0.980 no C21 . H211 . 0.969 no C22 . C23 . 1.423(4) yes C22 . C25 . 1.418(4) yes C23 . N24 . 1.142(4) yes C25 . N26 . 1.154(4) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C21 . H213 . N26 2_656 162.55(9) 0.980 2.560 3.507(4) yes C10 . H101 . O14 . 121.00 0.936 2.190 2.787(4) yes