#------------------------------------------------------------------------------ #$Date: 2019-10-11 11:06:48 +0300 (Fri, 11 Oct 2019) $ #$Revision: 219284 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/45/7234547.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_7234547 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 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 13.854(2) _cell_length_b 15.110(2) _cell_length_c 16.697(3) _cell_measurement_reflns_used 4972 _cell_measurement_temperature 150 _cell_measurement_theta_max 66.9630 _cell_measurement_theta_min 4.9480 _cell_volume 3495.2(9) _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 0.980 _diffrn_measured_fraction_theta_max 0.980 _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 0.079 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 16513 _diffrn_reflns_theta_full 67.889 _diffrn_reflns_theta_max 67.889 _diffrn_reflns_theta_min 5.077 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.742 _exptl_absorpt_correction_T_max 0.924 _exptl_absorpt_correction_T_min 0.825 _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 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1456 _exptl_crystal_preparation Luminescent _exptl_crystal_size_max 0.338 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.134 _refine_diff_density_max 0.32 _refine_diff_density_min -0.28 _refine_ls_extinction_coef 33.4(6) _refine_ls_extinction_method 'Larson (1970), Equation 22' _refine_ls_goodness_of_fit_ref 1.0253 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3095 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0621 _refine_ls_shift/su_max 0.0004325 _refine_ls_shift/su_mean 0.0000981 _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: 494. 773. 367. 82.7 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1105 _refine_ls_wR_factor_gt 0.0947 _refine_ls_wR_factor_ref 0.1105 _reflns_limit_h_max 16 _reflns_limit_h_min 0 _reflns_limit_k_max 17 _reflns_limit_k_min 0 _reflns_limit_l_max 19 _reflns_limit_l_min 0 _reflns_number_gt 2377 _reflns_number_total 3110 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 3.20 _oxford_diffrn_Wilson_scale 0.47 _oxford_refine_ls_r_factor_ref 0.0755 _oxford_refine_ls_scale 1.564(13) _oxford_reflns_number_all 3095 _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 3 _cod_original_sg_symbol_H-M 'P b c a ' _cod_database_code 7234547 _iucr_refine_instruction_details_constraints ; # # Punched on 13/11/13 at 09:54:14 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE C ( 6,X'S) H ( 61,X'S) H ( 62,X'S) H ( 63,X'S) RIDE C ( 7,X'S) H ( 71,X'S) H ( 72,X'S) H ( 73,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S) H ( 133,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 17,X'S) H ( 171,X'S) H ( 173,X'S) H ( 172,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 13/11/13 at 09:54:14 # #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 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 x+1/2,-y+1/2,-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_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 0.86765(13) 0.65499(11) 0.87586(11) 0.0468 1.0000 Uani . . . . . . C2 C 0.87199(15) 0.57313(15) 0.90451(15) 0.0390 1.0000 Uani . . . . . . C3 C 0.87504(15) 0.51121(16) 0.83977(14) 0.0385 1.0000 Uani . . . . . . C4 C 0.87312(15) 0.55568(16) 0.76849(15) 0.0391 1.0000 Uani . . . . . . C5 C 0.87033(17) 0.65414(15) 0.78701(14) 0.0407 1.0000 Uani . . . . . . C6 C 0.96238(19) 0.70088(15) 0.76344(16) 0.0505 1.0000 Uani . . . . . . H61 H 0.9645 0.7084 0.7050 0.0753 1.0000 Uiso R . . . . . H62 H 1.0175 0.6672 0.7834 0.0746 1.0000 Uiso R . . . . . H63 H 0.9618 0.7583 0.7892 0.0738 1.0000 Uiso R . . . . . C7 C 0.77967(19) 0.70083(14) 0.75954(16) 0.0487 1.0000 Uani . . . . . . H71 H 0.7832 0.7132 0.7020 0.0735 1.0000 Uiso R . . . . . H72 H 0.7232 0.6651 0.7714 0.0725 1.0000 Uiso R . . . . . H73 H 0.7767 0.7562 0.7898 0.0730 1.0000 Uiso R . . . . . C8 C 0.87416(16) 0.51590(17) 0.69140(15) 0.0415 1.0000 Uani . . . . . . C9 C 0.86983(16) 0.56215(16) 0.62199(16) 0.0424 1.0000 Uani . . . . . . C10 C 0.87070(15) 0.53271(16) 0.54038(15) 0.0389 1.0000 Uani . . . . . . C11 C 0.87793(15) 0.44405(16) 0.51398(16) 0.0392 1.0000 Uani . . . . . . O12 O 0.88122(13) 0.38192(11) 0.57176(11) 0.0511 1.0000 Uani . . . . . . C13 C 0.8882(2) 0.29104(17) 0.5490(2) 0.0627 1.0000 Uani . . . . . . H131 H 0.8878 0.2559 0.5981 0.0930 1.0000 Uiso R . . . . . H132 H 0.8345 0.2741 0.5142 0.0922 1.0000 Uiso R . . . . . H133 H 0.9489 0.2815 0.5213 0.0920 1.0000 Uiso R . . . . . C14 C 0.88074(17) 0.42509(17) 0.43287(16) 0.0419 1.0000 Uani . . . . . . C15 C 0.87586(16) 0.49267(17) 0.37738(16) 0.0421 1.0000 Uani . . . . . . O16 O 0.87913(13) 0.46669(12) 0.29921(11) 0.0523 1.0000 Uani . . . . . . C17 C 0.87566(19) 0.53362(19) 0.23949(17) 0.0563 1.0000 Uani . . . . . . H171 H 0.8787 0.5049 0.1874 0.0836 1.0000 Uiso R . . . . . H173 H 0.8151 0.5667 0.2430 0.0836 1.0000 Uiso R . . . . . H172 H 0.9298 0.5735 0.2451 0.0835 1.0000 Uiso R . . . . . C18 C 0.86771(17) 0.58012(17) 0.40090(16) 0.0462 1.0000 Uani . . . . . . C19 C 0.86510(18) 0.59806(16) 0.48172(16) 0.0461 1.0000 Uani . . . . . . H191 H 0.8584 0.6566 0.4973 0.0552 1.0000 Uiso R . . . . . H181 H 0.8626 0.6268 0.3636 0.0550 1.0000 Uiso R . . . . . H141 H 0.8866 0.3671 0.4166 0.0494 1.0000 Uiso R . . . . . H91 H 0.8665 0.6239 0.6280 0.0501 1.0000 Uiso R . . . . . H81 H 0.8777 0.4543 0.6893 0.0495 1.0000 Uiso R . . . . . C20 C 0.88089(17) 0.41746(16) 0.84834(16) 0.0428 1.0000 Uani . . . . . . N21 N 0.88599(18) 0.34196(14) 0.85163(17) 0.0612 1.0000 Uani . . . . . . C22 C 0.87215(16) 0.56133(15) 0.98566(16) 0.0405 1.0000 Uani . . . . . . C23 C 0.87942(17) 0.47612(16) 1.02250(16) 0.0425 1.0000 Uani . . . . . . N24 N 0.8857(2) 0.41155(16) 1.05626(16) 0.0618 1.0000 Uani . . . . . . C25 C 0.86951(18) 0.63554(18) 1.03846(16) 0.0467 1.0000 Uani . . . . . . N26 N 0.86775(19) 0.69494(15) 1.08071(16) 0.0650 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 0.0748(12) 0.0279(9) 0.0377(9) -0.0015(7) 0.0027(7) 0.0023(7) C2 0.0438(11) 0.0299(12) 0.0432(13) 0.0030(10) 0.0010(9) -0.0009(8) C3 0.0486(13) 0.0297(11) 0.0373(13) 0.0004(10) 0.0029(9) -0.0012(9) C4 0.0443(12) 0.0309(12) 0.0421(14) -0.0027(10) 0.0016(9) 0.0004(8) C5 0.0617(14) 0.0294(12) 0.0309(12) -0.0019(9) 0.0034(9) 0.0010(9) C6 0.0602(15) 0.0367(13) 0.0546(15) -0.0027(11) 0.0040(12) -0.0065(10) C7 0.0624(16) 0.0343(12) 0.0492(14) 0.0020(11) 0.0037(11) 0.0074(10) C8 0.0511(13) 0.0308(12) 0.0426(14) -0.0038(10) 0.0016(9) 0.0002(9) C9 0.0537(13) 0.0293(13) 0.0443(14) -0.0033(9) -0.0012(10) -0.0017(9) C10 0.0441(12) 0.0317(13) 0.0411(13) -0.0043(10) 0.0007(9) -0.0024(9) C11 0.0436(11) 0.0325(13) 0.0416(13) -0.0033(10) -0.0007(10) 0.0002(8) O12 0.0795(13) 0.0265(9) 0.0475(11) 0.0014(7) -0.0023(8) 0.0014(7) C13 0.093(2) 0.0263(13) 0.0692(19) -0.0027(12) -0.0055(15) 0.0033(12) C14 0.0488(13) 0.0319(12) 0.0452(14) -0.0057(11) -0.0021(10) 0.0003(9) C15 0.0461(13) 0.0403(13) 0.0400(13) -0.0056(11) -0.0020(9) -0.0022(9) O16 0.0737(12) 0.0445(11) 0.0388(10) -0.0091(8) 0.0012(8) -0.0006(8) C17 0.078(2) 0.0504(17) 0.0406(15) 0.0029(12) 0.0041(12) -0.0006(11) C18 0.0575(14) 0.0338(13) 0.0474(15) 0.0027(11) 0.0009(11) -0.0007(10) C19 0.0608(14) 0.0294(13) 0.0479(15) -0.0047(11) 0.0002(11) 0.0001(10) C20 0.0514(13) 0.0324(13) 0.0446(14) 0.0005(11) -0.0022(10) 0.0005(9) N21 0.0832(17) 0.0286(12) 0.0718(17) -0.0059(11) -0.0028(12) 0.0022(9) C22 0.0511(13) 0.0301(13) 0.0403(13) 0.0000(9) -0.0001(10) 0.0011(9) C23 0.0541(14) 0.0319(13) 0.0414(13) -0.0019(10) 0.0009(10) -0.0005(9) N24 0.0896(18) 0.0333(13) 0.0626(15) 0.0048(11) -0.0050(12) 0.0012(11) C25 0.0635(15) 0.0333(13) 0.0434(14) 0.0040(11) -0.0022(10) 0.0023(10) N26 0.106(2) 0.0361(13) 0.0525(14) -0.0077(11) -0.0011(13) 0.0058(11) 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 . C5 . 110.55(18) yes O1 . C2 . C3 . 109.8(2) yes O1 . C2 . C22 . 118.6(2) yes C3 . C2 . C22 . 131.6(2) yes C2 . C3 . C4 . 109.6(2) yes C2 . C3 . C20 . 125.1(2) yes C4 . C3 . C20 . 125.2(2) yes C3 . C4 . C5 . 107.7(2) yes C3 . C4 . C8 . 125.5(2) yes C5 . C4 . C8 . 126.8(2) yes C4 . C5 . O1 . 102.27(19) yes C4 . C5 . C6 . 112.53(19) yes O1 . C5 . C6 . 106.1(2) yes C4 . C5 . C7 . 114.6(2) yes O1 . C5 . C7 . 106.17(19) yes C6 . C5 . C7 . 113.9(2) yes C5 . C6 . H61 . 109.7 no C5 . C6 . H62 . 109.2 no H61 . C6 . H62 . 112.0 no C5 . C6 . H63 . 107.2 no H61 . C6 . H63 . 109.8 no H62 . C6 . H63 . 108.7 no C5 . C7 . H71 . 110.2 no C5 . C7 . H72 . 110.4 no H71 . C7 . H72 . 110.3 no C5 . C7 . H73 . 106.1 no H71 . C7 . H73 . 110.2 no H72 . C7 . H73 . 109.7 no C4 . C8 . C9 . 123.8(2) yes C4 . C8 . H81 . 117.1 no C9 . C8 . H81 . 119.1 no C8 . C9 . C10 . 130.8(2) yes C8 . C9 . H91 . 115.0 no C10 . C9 . H91 . 114.2 no C9 . C10 . C11 . 126.2(2) yes C9 . C10 . C19 . 116.6(2) yes C11 . C10 . C19 . 117.2(2) yes C10 . C11 . O12 . 116.1(2) yes C10 . C11 . C14 . 120.2(2) yes O12 . C11 . C14 . 123.7(2) yes C11 . O12 . C13 . 118.8(2) yes O12 . C13 . H131 . 107.4 no O12 . C13 . H132 . 111.0 no H131 . C13 . H132 . 110.6 no O12 . C13 . H133 . 109.2 no H131 . C13 . H133 . 108.9 no H132 . C13 . H133 . 109.7 no C11 . C14 . C15 . 120.1(2) yes C11 . C14 . H141 . 119.2 no C15 . C14 . H141 . 120.7 no C14 . C15 . O16 . 115.3(2) yes C14 . C15 . C18 . 121.3(2) yes O16 . C15 . C18 . 123.3(3) yes C15 . O16 . C17 . 117.7(2) yes O16 . C17 . H171 . 107.9 no O16 . C17 . H173 . 110.5 no H171 . C17 . H173 . 108.6 no O16 . C17 . H172 . 110.5 no H171 . C17 . H172 . 109.4 no H173 . C17 . H172 . 109.9 no C15 . C18 . C19 . 117.9(2) yes C15 . C18 . H181 . 122.2 no C19 . C18 . H181 . 119.9 no C10 . C19 . C18 . 123.2(2) yes C10 . C19 . H191 . 119.0 no C18 . C19 . H191 . 117.7 no C3 . C20 . N21 . 177.0(3) yes C2 . C22 . C23 . 122.9(2) yes C2 . C22 . C25 . 120.7(2) yes C23 . C22 . C25 . 116.3(2) yes C22 . C23 . N24 . 175.5(3) yes C22 . C25 . N26 . 179.8(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 . 1.328(3) yes O1 . C5 . 1.484(3) yes C2 . C3 . 1.430(3) yes C2 . C22 . 1.367(3) yes C3 . C4 . 1.367(3) yes C3 . C20 . 1.426(3) yes C4 . C5 . 1.520(3) yes C4 . C8 . 1.421(3) yes C5 . C6 . 1.510(3) yes C5 . C7 . 1.512(3) yes C6 . H61 . 0.984 no C6 . H62 . 0.976 no C6 . H63 . 0.969 no C7 . H71 . 0.981 no C7 . H72 . 0.971 no C7 . H73 . 0.977 no C8 . C9 . 1.355(4) yes C8 . H81 . 0.932 no C9 . C10 . 1.433(3) yes C9 . H91 . 0.940 no C10 . C11 . 1.414(3) yes C10 . C19 . 1.393(3) yes C11 . O12 . 1.347(3) yes C11 . C14 . 1.385(4) yes O12 . C13 . 1.428(3) yes C13 . H131 . 0.976 no C13 . H132 . 0.978 no C13 . H133 . 0.970 no C14 . C15 . 1.380(4) yes C14 . H141 . 0.921 no C15 . O16 . 1.364(3) yes C15 . C18 . 1.383(4) yes O16 . C17 . 1.421(3) yes C17 . H171 . 0.973 no C17 . H173 . 0.978 no C17 . H172 . 0.966 no C18 . C19 . 1.377(4) yes C18 . H181 . 0.943 no C19 . H191 . 0.927 no C20 . N21 . 1.144(3) yes C22 . C23 . 1.430(3) yes C22 . C25 . 1.427(3) yes C23 . N24 . 1.130(3) yes C25 . N26 . 1.142(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 C7 . H72 . O16 5_665 160.40(7) 0.971 2.489 3.418(4) yes C8 . H81 . O12 . 121.00 0.932 2.248 2.846(4) yes