#------------------------------------------------------------------------------ #$Date: 2016-03-20 23:21:50 +0000 (Sun, 20 Mar 2016) $ #$Revision: 178377 $ #$URL: svn://www.crystallography.net/cod/cif/4/00/07/4000707.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_4000707 loop_ _publ_author_name 'Massin, Julien' 'Dayoub, Wissam' 'Mulatier, Jean-Christophe' 'Aronica, Christophe' 'Bretonni\`ere, Yann' 'Andraud, Chantal' _publ_section_title ; Near-Infrared Solid-State Emitters Based on Isophorone: Synthesis, Crystal Structure and Spectroscopic Properties.† ; _journal_issue 3 _journal_name_full 'Chemistry of Materials' _journal_page_first 862 _journal_paper_doi 10.1021/cm102165r _journal_volume 23 _journal_year 2011 _chemical_formula_moiety 'C23 H26 N6' _chemical_formula_sum 'C23 H26 N6' _chemical_formula_weight 386.50 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 09-04-01 _audit_creation_method CRYSTALS_ver_12.86 _cell_angle_alpha 96.328(5) _cell_angle_beta 93.545(5) _cell_angle_gamma 95.462(5) _cell_formula_units_Z 2 _cell_length_a 7.671(5) _cell_length_b 8.752(5) _cell_length_c 16.741(5) _cell_measurement_reflns_used 0 _cell_measurement_temperature 293 _cell_measurement_theta_max 0 _cell_measurement_theta_min 0 _cell_volume 1109.0(10) _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _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 'SHELXS 86 (Sheldrick, 1986)' _diffrn_ambient_temperature 293 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.821 _diffrn_measurement_device Unknown _diffrn_measurement_device_type Serial _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 8444 _diffrn_reflns_theta_full 25.442 _diffrn_reflns_theta_max 29.584 _diffrn_reflns_theta_min 3.377 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 412 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.61 _refine_diff_density_min -0.32 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.7382 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 1997 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1441 _refine_ls_R_factor_gt 0.0870 _refine_ls_shift/su_max 0.000116 _refine_ls_structure_factor_coef F _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: 16.4 6.61 11.3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1088 _refine_ls_wR_factor_gt 0.0992 _refine_ls_wR_factor_ref 0.0989 _reflns_limit_h_max 9 _reflns_limit_h_min -10 _reflns_limit_k_max 11 _reflns_limit_k_min -11 _reflns_limit_l_max 22 _reflns_limit_l_min 0 _reflns_number_gt 2317 _reflns_number_total 5118 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _oxford_refine_ls_r_factor_ref 0.0827 _oxford_refine_ls_scale 6.40(3) _oxford_reflns_number_all 5110 _oxford_reflns_threshold_expression_ref I>3.0\s(I) _oxford_structure_analysis_title 'jm78 in P -1' _cod_data_source_file cm102165r_si_006.cif _cod_data_source_block JMazide _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P -1 ' _cod_database_code 4000707 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-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 C1 C 0.0873(5) 0.2619(5) 0.5452(2) 0.0514 1.0000 Uani C2 C -0.2888(6) 0.2856(5) 0.1803(2) 0.0561 1.0000 Uani N3 N -0.3814(5) 0.2702(5) 0.1064(2) 0.0693 1.0000 Uani C4 C 0.0119(5) 0.3146(5) 0.4061(2) 0.0554 1.0000 Uani C5 C 0.1369(5) 0.2053(5) 0.6838(2) 0.0609 1.0000 Uani C6 C -0.0954(5) 0.3061(5) 0.3317(2) 0.0528 1.0000 Uani C7 C -0.2637(6) 0.2265(5) 0.3175(2) 0.0591 1.0000 Uani C8 C -0.1231(6) 0.3690(5) 0.1946(2) 0.0627 1.0000 Uani C9 C -0.0275(5) 0.2511(5) 0.4732(2) 0.0573 1.0000 Uani C10 C 0.3974(5) 0.2970(5) 0.6113(2) 0.0519 1.0000 Uani C11 C 0.2666(5) 0.3489(5) 0.5498(2) 0.0542 1.0000 Uani C12 C -0.3574(6) 0.2143(5) 0.2444(3) 0.0604 1.0000 Uani C13 C 0.0317(5) 0.1962(5) 0.6099(3) 0.0628 1.0000 Uani C14 C -0.0304(5) 0.3781(5) 0.2679(2) 0.0597 1.0000 Uani C15 C 0.3136(6) 0.2959(6) 0.6912(3) 0.0664 1.0000 Uani C16 C 0.5648(6) 0.4108(6) 0.6220(3) 0.0770 1.0000 Uani C17 C 0.4483(6) 0.1379(6) 0.5812(3) 0.0714 1.0000 Uani C18 C 0.0775(7) 0.1389(7) 0.7474(3) 0.0788 1.0000 Uani C19 C -0.5426(6) 0.1653(6) 0.0886(3) 0.0755 1.0000 Uani C20 C -0.3173(7) 0.3550(6) 0.0419(3) 0.0756 1.0000 Uani C21 C 0.1819(8) 0.1477(8) 0.8224(4) 0.0993 1.0000 Uani C22 C -0.1874(8) 0.2698(8) -0.0058(3) 0.0984 1.0000 Uani C23 C -0.0932(9) 0.0547(9) 0.7430(4) 0.1089 1.0000 Uani N24 N -0.2292(9) -0.0094(10) 0.7380(5) 0.1734 1.0000 Uani N25 N 0.2644(9) 0.1570(9) 0.8809(3) 0.1451 1.0000 Uani C26 C -0.7049(8) 0.2387(9) 0.1090(4) 0.1143 1.0000 Uani N27 N -0.1287(8) 0.3602(8) -0.0712(4) 0.1354 1.0000 Uani N28 N -0.2299(10) 0.3525(9) -0.1305(4) 0.1443 1.0000 Uani N29 N -0.3148(15) 0.3671(13) -0.1816(5) 0.2521 1.0000 Uani H41 H 0.1251 0.3721 0.4082 0.0669 1.0000 Uiso H71 H -0.3161 0.1779 0.3598 0.0717 1.0000 Uiso H81 H -0.0729 0.4194 0.1523 0.0766 1.0000 Uiso H91 H -0.1402 0.1925 0.4732 0.0683 1.0000 Uiso H112 H 0.2532 0.4586 0.5636 0.0689 1.0000 Uiso H111 H 0.3116 0.3350 0.4960 0.0687 1.0000 Uiso H121 H -0.4708 0.1574 0.2368 0.0735 1.0000 Uiso H131 H -0.0809 0.1421 0.6052 0.0774 1.0000 Uiso H141 H 0.0814 0.4364 0.2767 0.0716 1.0000 Uiso H151 H 0.3906 0.2539 0.7307 0.0818 1.0000 Uiso H152 H 0.3003 0.4053 0.7132 0.0818 1.0000 Uiso H161 H 0.6547 0.3767 0.6580 0.1130 1.0000 Uiso H162 H 0.5370 0.5135 0.6428 0.1132 1.0000 Uiso H163 H 0.6138 0.4164 0.5690 0.1133 1.0000 Uiso H172 H 0.5223 0.0975 0.6204 0.1094 1.0000 Uiso H171 H 0.3443 0.0616 0.5688 0.1091 1.0000 Uiso H173 H 0.5120 0.1415 0.5338 0.1094 1.0000 Uiso H192 H -0.5378 0.0733 0.1184 0.0917 1.0000 Uiso H191 H -0.5525 0.1295 0.0314 0.0915 1.0000 Uiso H201 H -0.4168 0.3677 0.0056 0.0954 1.0000 Uiso H202 H -0.2614 0.4600 0.0641 0.0956 1.0000 Uiso H221 H -0.2495 0.1695 -0.0312 0.1248 1.0000 Uiso H222 H -0.0876 0.2496 0.0294 0.1241 1.0000 Uiso H262 H -0.8096 0.1722 0.0911 0.1751 1.0000 Uiso H261 H -0.7044 0.2627 0.1675 0.1751 1.0000 Uiso H263 H -0.7118 0.3418 0.0874 0.1743 1.0000 Uiso 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 0.046(2) 0.060(3) 0.048(2) 0.0103(18) -0.0026(18) -0.0020(18) C2 0.057(2) 0.064(3) 0.046(2) 0.0069(19) -0.0033(19) 0.001(2) N3 0.062(2) 0.092(3) 0.052(2) 0.0193(19) -0.0069(18) -0.005(2) C4 0.050(2) 0.060(3) 0.053(2) 0.0100(19) -0.0035(19) -0.0091(18) C5 0.051(2) 0.085(3) 0.050(2) 0.018(2) 0.009(2) 0.012(2) C6 0.049(2) 0.061(3) 0.046(2) 0.0094(18) -0.0009(19) -0.0062(19) C7 0.057(3) 0.067(3) 0.053(3) 0.021(2) 0.000(2) -0.012(2) C8 0.058(3) 0.080(3) 0.048(2) 0.017(2) 0.003(2) -0.009(2) C9 0.049(2) 0.067(3) 0.053(3) 0.011(2) -0.003(2) -0.0066(19) C10 0.044(2) 0.062(3) 0.048(2) 0.0109(18) -0.0002(17) -0.0033(18) C11 0.049(2) 0.061(3) 0.051(2) 0.0128(19) -0.0035(18) -0.0050(19) C12 0.055(2) 0.068(3) 0.055(3) 0.012(2) -0.007(2) -0.011(2) C13 0.047(2) 0.085(3) 0.057(3) 0.025(2) 0.002(2) -0.004(2) C14 0.049(2) 0.076(3) 0.050(2) 0.010(2) -0.0012(19) -0.018(2) C15 0.061(3) 0.088(3) 0.049(2) 0.008(2) -0.005(2) 0.005(2) C16 0.059(3) 0.091(4) 0.076(3) 0.014(3) -0.014(2) -0.017(2) C17 0.061(3) 0.072(3) 0.083(3) 0.015(2) 0.013(2) 0.008(2) C18 0.065(3) 0.122(4) 0.059(3) 0.038(3) 0.012(2) 0.021(3) C19 0.065(3) 0.103(4) 0.055(3) 0.009(2) -0.012(2) 0.004(3) C20 0.068(3) 0.108(4) 0.053(3) 0.025(3) -0.005(2) 0.002(3) C21 0.093(4) 0.155(6) 0.062(3) 0.039(3) 0.015(3) 0.038(4) C22 0.088(4) 0.144(5) 0.064(3) 0.016(3) 0.006(3) 0.013(4) C23 0.074(4) 0.170(6) 0.100(4) 0.085(4) 0.021(3) 0.011(4) N24 0.086(4) 0.260(9) 0.197(7) 0.161(7) 0.011(4) -0.025(5) N25 0.158(6) 0.231(7) 0.059(3) 0.040(4) -0.005(3) 0.069(5) C26 0.073(4) 0.158(6) 0.119(5) 0.045(5) 0.004(4) 0.019(4) N27 0.104(4) 0.198(7) 0.099(4) 0.028(4) 0.005(4) -0.021(4) N28 0.125(5) 0.206(7) 0.089(4) 0.021(4) -0.016(4) -0.042(5) N29 0.273(12) 0.319(13) 0.138(7) 0.113(8) -0.122(8) -0.118(10) 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 0.0033 0.0016 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 0.0061 0.0033 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_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C9 C1 C11 120.4(3) yes C9 C1 C13 119.8(4) yes C11 C1 C13 119.9(3) yes N3 C2 C8 122.1(4) yes N3 C2 C12 120.5(4) yes C8 C2 C12 117.4(4) yes C2 N3 C19 121.7(4) yes C2 N3 C20 120.5(4) yes C19 N3 C20 117.7(4) yes C6 C4 C9 127.8(4) yes C6 C4 H41 116.3 no C9 C4 H41 115.9 no C13 C5 C15 118.6(4) yes C13 C5 C18 121.4(4) yes C15 C5 C18 119.9(4) yes C4 C6 C7 124.3(4) yes C4 C6 C14 119.5(4) yes C7 C6 C14 116.2(4) yes C6 C7 C12 122.4(4) yes C6 C7 H71 119.7 no C12 C7 H71 117.9 no C2 C8 C14 121.0(4) yes C2 C8 H81 119.5 no C14 C8 H81 119.5 no C1 C9 C4 125.0(4) yes C1 C9 H91 116.9 no C4 C9 H91 118.0 no C11 C10 C15 108.4(3) yes C11 C10 C16 109.5(3) yes C15 C10 C16 109.5(4) yes C11 C10 C17 110.0(3) yes C15 C10 C17 111.4(4) yes C16 C10 C17 108.0(4) yes C10 C11 C1 113.8(3) yes C10 C11 H112 109.6 no C1 C11 H112 107.6 no C10 C11 H111 109.3 no C1 C11 H111 108.0 no H112 C11 H111 108.5 no C2 C12 C7 120.6(4) yes C2 C12 H121 119.4 no C7 C12 H121 119.9 no C5 C13 C1 122.8(4) yes C5 C13 H131 119.2 no C1 C13 H131 118.0 no C6 C14 C8 122.3(4) yes C6 C14 H141 117.8 no C8 C14 H141 119.9 no C10 C15 C5 113.0(3) yes C10 C15 H151 110.3 no C5 C15 H151 109.1 no C10 C15 H152 108.7 no C5 C15 H152 108.5 no H151 C15 H152 107.1 no C10 C16 H161 111.5 no C10 C16 H162 110.0 no H161 C16 H162 109.9 no C10 C16 H163 109.0 no H161 C16 H163 107.5 no H162 C16 H163 108.8 no C10 C17 H172 112.2 no C10 C17 H171 111.6 no H172 C17 H171 106.2 no C10 C17 H173 111.0 no H172 C17 H173 106.8 no H171 C17 H173 108.7 no C5 C18 C21 122.0(5) yes C5 C18 C23 121.4(5) yes C21 C18 C23 116.6(5) yes N3 C19 C26 113.5(5) yes N3 C19 H192 110.7 no C26 C19 H192 107.9 no N3 C19 H191 108.2 no C26 C19 H191 108.5 no H192 C19 H191 107.8 no N3 C20 C22 112.1(5) yes N3 C20 H201 108.2 no C22 C20 H201 108.4 no N3 C20 H202 110.6 no C22 C20 H202 109.4 no H201 C20 H202 108.0 no C18 C21 N25 178.9(8) yes C20 C22 N27 109.7(6) yes C20 C22 H221 107.7 no N27 C22 H221 108.1 no C20 C22 H222 110.9 no N27 C22 H222 111.3 no H221 C22 H222 109.0 no C18 C23 N24 178.1(6) yes C19 C26 H262 112.2 no C19 C26 H261 109.5 no H262 C26 H261 107.6 no C19 C26 H263 113.2 no H262 C26 H263 109.3 no H261 C26 H263 104.7 no C22 N27 N28 116.3(6) yes N27 N28 N29 170.1(11) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C9 1.438(5) yes C1 C11 1.501(5) yes C1 C13 1.353(6) yes C2 N3 1.374(5) yes C2 C8 1.398(6) yes C2 C12 1.405(6) yes N3 C19 1.462(6) yes N3 C20 1.461(6) yes C4 C6 1.441(5) yes C4 C9 1.345(6) yes C4 H41 0.958 no C5 C13 1.425(6) yes C5 C15 1.494(6) yes C5 C18 1.351(6) yes C6 C7 1.401(6) yes C6 C14 1.393(6) yes C7 C12 1.369(6) yes C7 H71 0.955 no C8 C14 1.371(6) yes C8 H81 0.955 no C9 H91 0.963 no C10 C11 1.528(5) yes C10 C15 1.520(6) yes C10 C16 1.537(6) yes C10 C17 1.523(6) yes C11 H112 0.979 no C11 H111 0.985 no C12 H121 0.954 no C13 H131 0.939 no C14 H141 0.949 no C15 H151 0.984 no C15 H152 1.004 no C16 H161 0.978 no C16 H162 0.975 no C16 H163 0.988 no C17 H172 0.960 no C17 H171 0.987 no C17 H173 0.959 no C18 C21 1.438(8) yes C18 C23 1.434(9) yes C19 C26 1.495(8) yes C19 H192 0.996 no C19 H191 0.969 no C20 C22 1.515(8) yes C20 H201 0.968 no C20 H202 0.998 no C21 N25 1.124(7) yes C22 N27 1.487(8) yes C22 H221 0.995 no C22 H222 0.979 no C23 N24 1.130(8) yes C26 H262 0.958 no C26 H261 0.979 no C26 H263 1.013 no N27 N28 1.214(8) yes N28 N29 1.068(9) yes