#------------------------------------------------------------------------------ #$Date: 2019-10-11 11:06:48 +0300 (Fri, 11 Oct 2019) $ #$Revision: 219284 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/45/7234545.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_7234545 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 'C19 H15 N3 O2' _chemical_formula_sum 'C19 H15 N3 O2' _chemical_formula_weight 317.34 _space_group_IT_number 11 _space_group_name_Hall '-P 2yb' _space_group_name_H-M_alt 'P 1 21/m 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary other _cell_angle_alpha 90 _cell_angle_beta 101.360(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.0110(9) _cell_length_b 6.9999(6) _cell_length_c 11.5760(10) _cell_measurement_reflns_used 5464 _cell_measurement_temperature 100 _cell_measurement_theta_max 66.3129 _cell_measurement_theta_min 3.8918 _cell_volume 795.31(12) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _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 'Superflip (Palatinus & Chapuis, 2007)' _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 10.4685 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.045 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 8943 _diffrn_reflns_theta_full 66.416 _diffrn_reflns_theta_max 66.416 _diffrn_reflns_theta_min 3.895 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.715 _exptl_absorpt_correction_T_max 0.933 _exptl_absorpt_correction_T_min 0.742 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) 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 brown _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 332 _exptl_crystal_preparation Luminescent _exptl_crystal_size_max 0.511 _exptl_crystal_size_mid 0.345 _exptl_crystal_size_min 0.094 _refine_diff_density_max 0.69 _refine_diff_density_min -0.29 _refine_ls_extinction_coef 15.9(6) _refine_ls_extinction_method 'Larson (1970), Equation 22' _refine_ls_goodness_of_fit_ref 0.9391 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 150 _refine_ls_number_reflns 1533 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0448 _refine_ls_shift/su_max 0.0032352 _refine_ls_shift/su_mean 0.0000351 _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: 0.147E+04 0.247E+04 0.147E+04 588. 127. ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1059 _refine_ls_wR_factor_gt 0.1043 _refine_ls_wR_factor_ref 0.1059 _reflns_limit_h_max 11 _reflns_limit_h_min -11 _reflns_limit_k_max 8 _reflns_limit_k_min 0 _reflns_limit_l_max 13 _reflns_limit_l_min 0 _reflns_number_gt 1448 _reflns_number_total 1533 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 1.41 _oxford_diffrn_Wilson_scale 0.03 _oxford_refine_ls_r_factor_ref 0.0465 _oxford_refine_ls_scale 6.2(2) _oxford_reflns_number_all 1533 _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 1 _cod_depositor_comments ; The following automatic conversions were performed: data item '_atom_sites_solution_primary' value 'Other' was changed to 'other' in accordance with the built-in table derived from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated on 2014-11-21. Automatic conversion script Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas ; _cod_original_sg_symbol_H-M 'P 21/m ' _cod_database_code 7234545 _iucr_refine_instruction_details_constraints ; # # Punched on 29/05/12 at 14:27:26 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE C ( 6,X'S) H ( 63,X'S) H ( 62,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 14,X'S) H ( 142,X'S) H ( 143,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 29/05/12 at 14:27:26 # #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 -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 0.47818(14) 0.7500 -0.30866(12) 0.0201 1.0000 Uani S T . . . . C2 C 0.6051(2) 0.7500 -0.24536(18) 0.0179 1.0000 Uani S T . . . . C3 C 0.6011(2) 0.7500 -0.12130(17) 0.0190 1.0000 Uani S T . . . . C4 C 0.4686(2) 0.7500 -0.10764(17) 0.0192 1.0000 Uani S T . . . . C5 C 0.3778(2) 0.7500 -0.22930(17) 0.0191 1.0000 Uani S T . . . . C6 C 0.29319(14) 0.5696(2) -0.25790(12) 0.0233 1.0000 Uani . . . . . . H63 H 0.3490 0.4570 -0.2374 0.0344 1.0000 Uiso R . . . . . H62 H 0.2549 0.5675 -0.3420 0.0327 1.0000 Uiso R . . . . . H61 H 0.2207 0.5685 -0.2132 0.0331 1.0000 Uiso R . . . . . C7 C 0.4303(2) 0.750000(7) 0.00545(19) 0.0242 1.0000 Uani S T . . . . C8 C 0.3023(2) 0.750000(7) 0.02493(19) 0.0235 1.0000 Uani S T . . . . C9 C 0.2634(2) 0.7500 0.14032(19) 0.0237 1.0000 Uani S T . . . . C10 C 0.3574(2) 0.750000(7) 0.2489(2) 0.0241 1.0000 Uani S T . . . . C11 C 0.3138(2) 0.750000(7) 0.35523(19) 0.0218 1.0000 Uani S T . . . . C12 C 0.1741(2) 0.7500 0.35490(17) 0.0192 1.0000 Uani S T . . . . O13 O 0.13804(14) 0.7500 0.46261(12) 0.0227 1.0000 Uani S T . . . . C14 C -0.0039(2) 0.750000(7) 0.4652(2) 0.0288 1.0000 Uani S T . . . . H142 H -0.0462 0.6356 0.4268 0.0418 1.0000 Uiso R . . . . . H143 H -0.0130 0.7500 0.5480 0.0431 1.0000 Uiso RS . . . . . C15 C 0.0805(2) 0.750000(7) 0.24810(18) 0.0234 1.0000 Uani S T . . . . C16 C 0.1260(2) 0.750000(7) 0.14316(19) 0.0262 1.0000 Uani S T . . . . H161 H 0.0603 0.7500 0.0703 0.0317 1.0000 Uiso RS . . . . . H151 H -0.0159 0.7500 0.2477 0.0290 1.0000 Uiso RS . . . . . H111 H 0.3742 0.7500 0.4278 0.0254 1.0000 Uiso RS . . . . . H101 H 0.4527 0.7500 0.2529 0.0295 1.0000 Uiso RS . . . . . H81 H 0.2305 0.7500 -0.0449 0.0285 1.0000 Uiso RS . . . . . H71 H 0.5018 0.7500 0.0763 0.0297 1.0000 Uiso RS . . . . . C17 C 0.7156(2) 0.7500 -0.02614(18) 0.0226 1.0000 Uani S T . . . . N18 N 0.80148(19) 0.7500 0.05570(16) 0.0316 1.0000 Uani S T . . . . C19 C 0.7135(2) 0.7500 -0.30124(18) 0.0196 1.0000 Uani S T . . . . C20 C 0.6894(2) 0.7500 -0.42745(18) 0.0216 1.0000 Uani S T . . . . N21 N 0.6689(2) 0.7500 -0.52900(17) 0.0311 1.0000 Uani S T . . . . C22 C 0.8519(2) 0.7500 -0.23959(18) 0.0214 1.0000 Uani S T . . . . N23 N 0.96503(19) 0.7500 -0.19418(18) 0.0301 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 0.0165(7) 0.0283(8) 0.0158(7) 0.0000 0.0039(5) 0.0000 C2 0.0189(10) 0.0151(9) 0.0196(10) 0.0000 0.0039(8) 0.0000 C3 0.0199(10) 0.0186(10) 0.0179(10) 0.0000 0.0025(8) 0.0000 C4 0.0227(10) 0.0152(9) 0.0201(10) 0.0000 0.0052(8) 0.0000 C5 0.0166(9) 0.0231(10) 0.0191(10) 0.0000 0.0071(8) 0.0000 C6 0.0220(7) 0.0246(8) 0.0243(7) -0.0017(6) 0.0070(6) -0.0014(6) C7 0.0289(12) 0.0241(11) 0.0204(10) 0.0000 0.0066(9) 0.0000 C8 0.0246(11) 0.0217(10) 0.0236(11) 0.0000 0.0029(9) 0.0000 C9 0.0321(12) 0.0172(10) 0.0223(10) 0.0000 0.0064(9) 0.0000 C10 0.0220(10) 0.0186(10) 0.0349(12) 0.0000 0.0135(9) 0.0000 C11 0.0203(10) 0.0218(10) 0.0238(11) 0.0000 0.0055(8) 0.0000 C12 0.0236(10) 0.0180(10) 0.0177(10) 0.0000 0.0085(8) 0.0000 O13 0.0179(7) 0.0356(9) 0.0154(7) 0.0000 0.0053(5) 0.0000 C14 0.0187(11) 0.0427(13) 0.0272(11) 0.0000 0.0099(9) 0.0000 C15 0.0244(11) 0.0252(11) 0.0202(10) 0.0000 0.0035(8) 0.0000 C16 0.0299(11) 0.0274(11) 0.0206(10) 0.0000 0.0036(9) 0.0000 C17 0.0231(11) 0.0241(11) 0.0216(10) 0.0000 0.0071(9) 0.0000 N18 0.0247(10) 0.0463(12) 0.0225(10) 0.0000 0.0011(8) 0.0000 C19 0.0191(10) 0.0183(10) 0.0216(10) 0.0000 0.0048(8) 0.0000 C20 0.0201(10) 0.0224(10) 0.0242(11) 0.0000 0.0090(8) 0.0000 N21 0.0328(11) 0.0368(11) 0.0270(11) 0.0000 0.0139(8) 0.0000 C22 0.0226(12) 0.0191(10) 0.0247(11) 0.0000 0.0096(9) 0.0000 N23 0.0205(10) 0.0325(11) 0.0374(11) 0.0000 0.0063(8) 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' 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' 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' 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 . 110.25(15) yes O1 . C2 . C3 . 109.61(17) yes O1 . C2 . C19 . 119.85(18) yes C3 . C2 . C19 . 130.53(19) yes C2 . C3 . C4 . 109.44(17) yes C2 . C3 . C17 . 126.35(18) yes C4 . C3 . C17 . 124.20(19) yes C3 . C4 . C5 . 108.09(17) yes C3 . C4 . C7 . 123.07(19) yes C5 . C4 . C7 . 128.84(19) yes C6 3_565 C5 . C4 . 114.09(10) yes C6 3_565 C5 . O1 . 106.28(10) yes C4 . C5 . O1 . 102.61(15) yes C6 3_565 C5 . C6 . 112.34(16) yes C4 . C5 . C6 . 114.09(10) yes O1 . C5 . C6 . 106.28(10) yes C5 . C6 . H63 . 110.6 no C5 . C6 . H62 . 108.8 no H63 . C6 . H62 . 109.1 no C5 . C6 . H61 . 109.5 no H63 . C6 . H61 . 108.6 no H62 . C6 . H61 . 110.2 no C4 . C7 . C8 . 126.0(2) yes C4 . C7 . H71 . 118.8 no C8 . C7 . H71 . 115.1 no C7 . C8 . C9 . 126.0(2) yes C7 . C8 . H81 . 115.8 no C9 . C8 . H81 . 118.3 no C8 . C9 . C10 . 124.1(2) yes C8 . C9 . C16 . 117.8(2) yes C10 . C9 . C16 . 118.0(2) yes C9 . C10 . C11 . 121.3(2) yes C9 . C10 . H101 . 122.1 no C11 . C10 . H101 . 116.6 no C10 . C11 . C12 . 119.21(19) yes C10 . C11 . H111 . 122.6 no C12 . C11 . H111 . 118.2 no C11 . C12 . O13 . 116.24(17) yes C11 . C12 . C15 . 119.95(19) yes O13 . C12 . C15 . 123.81(19) yes C12 . O13 . C14 . 117.58(16) yes O13 . C14 . H142 3_565 109.6 no O13 . C14 . H142 . 109.6 no H142 3_565 C14 . H142 . 111.0 no O13 . C14 . H143 . 107.7 no H142 3_565 C14 . H143 . 109.4 no H142 . C14 . H143 . 109.4 no C12 . C15 . C16 . 119.9(2) yes C12 . C15 . H151 . 120.1 no C16 . C15 . H151 . 120.0 no C9 . C16 . C15 . 121.6(2) yes C9 . C16 . H161 . 119.4 no C15 . C16 . H161 . 119.0 no C3 . C17 . N18 . 175.2(2) yes C2 . C19 . C20 . 119.46(19) yes C2 . C19 . C22 . 123.05(19) yes C20 . C19 . C22 . 117.49(18) yes C19 . C20 . N21 . 179.5(2) yes C19 . C22 . N23 . 177.3(2) 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 . 1.336(2) yes O1 . C5 . 1.489(2) yes C2 . C3 . 1.445(3) yes C2 . C19 . 1.369(3) yes C3 . C4 . 1.366(3) yes C3 . C17 . 1.425(3) yes C4 . C5 . 1.519(3) yes C4 . C7 . 1.435(3) yes C5 . C6 3_565 1.5202(18) yes C5 . C6 . 1.5202(18) yes C6 . H63 . 0.968 no C6 . H62 . 0.974 no C6 . H61 . 0.970 no C7 . C8 . 1.344(3) yes C7 . H71 . 0.976 no C8 . C9 . 1.463(3) yes C8 . H81 . 0.971 no C9 . C10 . 1.414(3) yes C9 . C16 . 1.382(3) yes C10 . C11 . 1.385(3) yes C10 . H101 . 0.947 no C11 . C12 . 1.397(3) yes C11 . H111 . 0.933 no C12 . O13 . 1.365(2) yes C12 . C15 . 1.397(3) yes O13 . C14 . 1.428(2) yes C14 . H142 3_565 0.972 no C14 . H142 . 0.972 no C14 . H143 . 0.980 no C15 . C16 . 1.379(3) yes C15 . H151 . 0.964 no C16 . H161 . 0.962 no C17 . N18 . 1.147(3) yes C19 . C20 . 1.433(3) yes C19 . C22 . 1.428(3) yes C20 . N21 . 1.153(3) yes C22 . N23 . 1.151(3) 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 C16 . H161 . N18 1_455 124.40(7) 0.962 2.563 3.207(2) yes C15 . H151 . N18 1_455 122.79(7) 0.964 2.585 3.211(2) yes