#------------------------------------------------------------------------------ #$Date: 2019-10-11 11:06:48 +0300 (Fri, 11 Oct 2019) $ #$Revision: 219284 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/45/7234550.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_7234550 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 62 _space_group_name_Hall '-P 2ac 2n' _space_group_name_H-M_alt 'P n m a' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_space_group_name_H-M 'P n m 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 4 _cell_length_a 17.1210(10) _cell_length_b 6.9428(5) _cell_length_c 15.4460(10) _cell_measurement_reflns_used 5414 _cell_measurement_temperature 150 _cell_measurement_theta_max 66.9540 _cell_measurement_theta_min 5.1410 _cell_volume 1836.0(2) _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 0.994 _diffrn_measured_fraction_theta_max 0.994 _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 0.063 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 11309 _diffrn_reflns_theta_full 67.001 _diffrn_reflns_theta_max 67.001 _diffrn_reflns_theta_min 3.854 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.706 _exptl_absorpt_correction_T_max 0.903 _exptl_absorpt_correction_T_min 0.762 _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 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 728 _exptl_crystal_preparation Luminescent _exptl_crystal_size_max 0.553 _exptl_crystal_size_mid 0.325 _exptl_crystal_size_min 0.144 _refine_diff_density_max 0.25 _refine_diff_density_min -0.17 _refine_ls_extinction_coef 114(3) _refine_ls_extinction_method 'Larson (1970), Equation 22' _refine_ls_goodness_of_fit_ref 1.0111 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 162 _refine_ls_number_reflns 1761 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0392 _refine_ls_shift/su_max 0.0006934 _refine_ls_shift/su_mean 0.0000383 _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: 0.152E+04 0.257E+04 0.157E+04 646. 143. ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1128 _refine_ls_wR_factor_gt 0.1081 _refine_ls_wR_factor_ref 0.1128 _reflns_limit_h_max 20 _reflns_limit_h_min 0 _reflns_limit_k_max 8 _reflns_limit_k_min 0 _reflns_limit_l_max 18 _reflns_limit_l_min 0 _reflns_number_gt 1599 _reflns_number_total 1772 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 2.19 _oxford_diffrn_Wilson_scale 0.08 _oxford_refine_ls_r_factor_ref 0.0422 _oxford_refine_ls_scale 4.05(11) _oxford_reflns_number_all 1761 _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 6 _cod_original_sg_symbol_H-M 'P n m a ' _cod_database_code 7234550 _iucr_refine_instruction_details_constraints ; # # Punched on 30/10/13 at 17:11:01 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE C ( 3,X'S) H ( 31,X'S) H ( 33,X'S) H ( 32,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 11,X'S) H ( 112,X'S) H ( 113,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 16,X'S) H ( 163,X'S) H ( 162,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 30/10/13 at 17:11:01 # #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+1/2,y+1/2,z+1/2 x+1/2,-y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 -x,y+1/2,-z x,-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 0.54692(6) 0.2500 0.72805(7) 0.0311 1.0000 Uani S T . . . . C2 C 0.47402(9) 0.2500 0.67611(11) 0.0277 1.0000 Uani S T . . . . C3 C 0.42911(7) 0.06902(18) 0.70079(8) 0.0347 1.0000 Uani . . . . . . H31 H 0.3790 0.0682 0.6693 0.0508 1.0000 Uiso R . . . . . H33 H 0.4579 -0.0456 0.6854 0.0519 1.0000 Uiso R . . . . . H32 H 0.4182 0.0710 0.7616 0.0510 1.0000 Uiso R . . . . . C4 C 0.50469(10) 0.2500 0.58430(10) 0.0257 1.0000 Uani S T . . . . C5 C 0.46144(9) 0.250000(7) 0.50485(11) 0.0285 1.0000 Uani S T . . . . C6 C 0.38363(10) 0.250000(7) 0.49438(11) 0.0283 1.0000 Uani S T . . . . C7 C 0.34429(10) 0.2500 0.40987(10) 0.0271 1.0000 Uani S T . . . . C8 C 0.38568(10) 0.250000(7) 0.33229(11) 0.0294 1.0000 Uani S T . . . . C9 C 0.34619(10) 0.2500 0.25320(11) 0.0293 1.0000 Uani S T . . . . O10 O 0.39265(7) 0.2500 0.18178(8) 0.0418 1.0000 Uani S T . . . . C11 C 0.35584(12) 0.250000(7) 0.09847(11) 0.0406 1.0000 Uani S T . . . . H113 H 0.3974 0.2500 0.0565 0.0610 1.0000 Uiso RS . . . . . H112 H 0.3244 0.1350 0.0919 0.0603 1.0000 Uiso R . . . . . C12 C 0.26522(10) 0.250000(7) 0.25152(11) 0.0287 1.0000 Uani S T . . . . C13 C 0.22412(10) 0.2500 0.33006(11) 0.0275 1.0000 Uani S T . . . . C14 C 0.26260(10) 0.250000(7) 0.40915(11) 0.0285 1.0000 Uani S T . . . . H141 H 0.2341 0.2500 0.4612 0.0346 1.0000 Uiso RS . . . . . O15 O 0.14510(7) 0.2500 0.32177(8) 0.0357 1.0000 Uani S T . . . . C16 C 0.09973(11) 0.250000(7) 0.39949(14) 0.0472 1.0000 Uani S T . . . . H162 H 0.0450 0.2500 0.3820 0.0697 1.0000 Uiso RS . . . . . H163 H 0.1121 0.3666 0.4334 0.0703 1.0000 Uiso R . . . . . H121 H 0.2378 0.2500 0.1983 0.0348 1.0000 Uiso RS . . . . . H81 H 0.4409 0.2500 0.3303 0.0356 1.0000 Uiso RS . . . . . H61 H 0.3503 0.2500 0.5448 0.0341 1.0000 Uiso RS . . . . . H51 H 0.4930 0.2500 0.4535 0.0350 1.0000 Uiso RS . . . . . C17 C 0.58414(10) 0.2500 0.58738(10) 0.0255 1.0000 Uani S T . . . . C18 C 0.60942(10) 0.2500 0.67686(10) 0.0257 1.0000 Uani S T . . . . C19 C 0.68327(10) 0.2500 0.71012(10) 0.0284 1.0000 Uani S T . . . . C20 C 0.69587(10) 0.2500 0.80141(12) 0.0346 1.0000 Uani S T . . . . N21 N 0.70891(11) 0.2500 0.87420(11) 0.0508 1.0000 Uani S T . . . . C22 C 0.75106(10) 0.2500 0.65648(11) 0.0308 1.0000 Uani S T . . . . N23 N 0.80748(9) 0.2500 0.61646(11) 0.0427 1.0000 Uani S T . . . . C24 C 0.63295(9) 0.2500 0.51247(11) 0.0290 1.0000 Uani S T . . . . N25 N 0.66693(9) 0.2500 0.44903(10) 0.0421 1.0000 Uani S T . . . . 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 0.0234(6) 0.0468(7) 0.0231(6) 0.0000 -0.0018(4) 0.0000 C2 0.0204(8) 0.0382(9) 0.0244(8) 0.0000 -0.0007(6) 0.0000 C3 0.0307(6) 0.0376(7) 0.0358(6) 0.0036(5) 0.0040(5) -0.0012(5) C4 0.0245(8) 0.0281(8) 0.0245(8) 0.0000 -0.0015(6) 0.0000 C5 0.0248(8) 0.0358(9) 0.0248(8) 0.0000 -0.0023(7) 0.0000 C6 0.0262(9) 0.0316(8) 0.0272(8) 0.0000 -0.0016(7) 0.0000 C7 0.0265(8) 0.0269(8) 0.0279(9) 0.0000 -0.0038(6) 0.0000 C8 0.0209(8) 0.0353(9) 0.0320(9) 0.0000 -0.0024(6) 0.0000 C9 0.0270(9) 0.0340(8) 0.0270(8) 0.0000 0.0002(7) 0.0000 O10 0.0277(7) 0.0700(9) 0.0277(7) 0.0000 0.0002(5) 0.0000 C11 0.0370(10) 0.0592(12) 0.0255(9) 0.0000 -0.0015(7) 0.0000 C12 0.0266(9) 0.0320(8) 0.0275(8) 0.0000 -0.0067(7) 0.0000 C13 0.0240(9) 0.0276(8) 0.0310(8) 0.0000 -0.0045(7) 0.0000 C14 0.0258(9) 0.0318(8) 0.0278(9) 0.0000 -0.0006(6) 0.0000 O15 0.0214(6) 0.0511(8) 0.0346(7) 0.0000 -0.0034(5) 0.0000 C16 0.0234(9) 0.0749(14) 0.0433(10) 0.0000 0.0028(8) 0.0000 C17 0.0240(8) 0.0296(8) 0.0230(8) 0.0000 -0.0005(6) 0.0000 C18 0.0255(9) 0.0285(8) 0.0232(8) 0.0000 -0.0004(6) 0.0000 C19 0.0276(8) 0.0300(8) 0.0275(8) 0.0000 -0.0059(7) 0.0000 C20 0.0302(9) 0.0402(10) 0.0335(10) 0.0000 -0.0080(7) 0.0000 N21 0.0546(11) 0.0634(11) 0.0345(10) 0.0000 -0.0168(8) 0.0000 C22 0.0249(9) 0.0334(9) 0.0341(9) 0.0000 -0.0088(7) 0.0000 N23 0.0281(8) 0.0536(10) 0.0464(9) 0.0000 -0.0025(7) 0.0000 C24 0.0219(8) 0.0376(9) 0.0275(9) 0.0000 -0.0018(7) 0.0000 N25 0.0295(8) 0.0659(11) 0.0308(8) 0.0000 0.0017(7) 0.0000 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 . C18 . 110.81(12) yes C3 8_555 C2 . O1 . 106.84(9) yes C3 8_555 C2 . C3 . 111.33(14) yes O1 . C2 . C3 . 106.84(9) yes C3 8_555 C2 . C4 . 114.23(8) yes O1 . C2 . C4 . 102.41(12) yes C3 . C2 . C4 . 114.23(8) yes C2 . C3 . H31 . 108.7 no C2 . C3 . H33 . 111.1 no H31 . C3 . H33 . 108.5 no C2 . C3 . H32 . 109.4 no H31 . C3 . H32 . 108.3 no H33 . C3 . H32 . 110.6 no C2 . C4 . C5 . 128.57(15) yes C2 . C4 . C17 . 108.32(13) yes C5 . C4 . C17 . 123.11(14) yes C4 . C5 . C6 . 128.02(16) yes C4 . C5 . H51 . 114.6 no C6 . C5 . H51 . 117.4 no C5 . C6 . C7 . 124.21(16) yes C5 . C6 . H61 . 119.3 no C7 . C6 . H61 . 116.5 no C6 . C7 . C8 . 122.11(15) yes C6 . C7 . C14 . 117.74(15) yes C8 . C7 . C14 . 120.15(15) yes C7 . C8 . C9 . 120.43(15) yes C7 . C8 . H81 . 122.4 no C9 . C8 . H81 . 117.1 no C8 . C9 . O10 . 115.24(14) yes C8 . C9 . C12 . 120.04(16) yes O10 . C9 . C12 . 124.72(15) yes C9 . O10 . C11 . 118.11(13) yes O10 . C11 . H112 8_555 109.8 no O10 . C11 . H113 . 106.2 no H112 8_555 C11 . H113 . 109.9 no O10 . C11 . H112 . 109.8 no H112 8_555 C11 . H112 . 111.2 no H113 . C11 . H112 . 109.9 no C9 . C12 . C13 . 119.04(16) yes C9 . C12 . H121 . 120.8 no C13 . C12 . H121 . 120.2 no C12 . C13 . C14 . 121.55(16) yes C12 . C13 . O15 . 114.71(14) yes C14 . C13 . O15 . 123.74(15) yes C7 . C14 . C13 . 118.79(15) yes C7 . C14 . H141 . 120.8 no C13 . C14 . H141 . 120.4 no C13 . O15 . C16 . 117.50(14) yes H163 8_555 C16 . O15 . 109.2 no H163 8_555 C16 . H162 . 110.7 no O15 . C16 . H162 . 106.8 no H163 8_555 C16 . H163 . 110.2 no O15 . C16 . H163 . 109.2 no H162 . C16 . H163 . 110.7 no C4 . C17 . C18 . 109.40(13) yes C4 . C17 . C24 . 123.83(14) yes C18 . C17 . C24 . 126.77(15) yes C17 . C18 . O1 . 109.07(13) yes C17 . C18 . C19 . 129.50(15) yes O1 . C18 . C19 . 121.43(14) yes C18 . C19 . C20 . 120.81(15) yes C18 . C19 . C22 . 122.36(14) yes C20 . C19 . C22 . 116.82(15) yes C19 . C20 . N21 . 177.5(2) yes C19 . C22 . N23 . 177.09(19) yes C17 . C24 . N25 . 174.86(17) 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 . 1.4837(19) yes O1 . C18 . 1.330(2) yes C2 . C3 8_555 1.5216(15) yes C2 . C3 . 1.5216(15) yes C2 . C4 . 1.512(2) yes C3 . H31 . 0.987 no C3 . H33 . 0.966 no C3 . H32 . 0.958 no C4 . C5 . 1.433(2) yes C4 . C17 . 1.361(2) yes C5 . C6 . 1.342(2) yes C5 . H51 . 0.960 no C6 . C7 . 1.469(2) yes C6 . H61 . 0.965 no C7 . C8 . 1.392(2) yes C7 . C14 . 1.399(2) yes C8 . C9 . 1.396(2) yes C8 . H81 . 0.947 no C9 . O10 . 1.360(2) yes C9 . C12 . 1.387(2) yes O10 . C11 . 1.433(2) yes C11 . H112 8_555 0.968 no C11 . H113 . 0.962 no C11 . H112 . 0.968 no C12 . C13 . 1.402(2) yes C12 . H121 . 0.947 no C13 . C14 . 1.388(2) yes C13 . O15 . 1.359(2) yes C14 . H141 . 0.941 no O15 . C16 . 1.430(2) yes C16 . H163 8_555 0.987 no C16 . H162 . 0.976 no C16 . H163 . 0.987 no C17 . C18 . 1.448(2) yes C17 . C24 . 1.427(2) yes C18 . C19 . 1.365(2) yes C19 . C20 . 1.426(2) yes C19 . C22 . 1.426(2) yes C20 . N21 . 1.146(2) yes C22 . N23 . 1.147(2) yes C24 . N25 . 1.140(2) 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 C14 . H141 . N21 4_456 158.32(6) 0.941 2.579 3.4704(16) yes C12 . H121 . N25 4_455 178.35(5) 0.947 2.579 3.5253(16) yes