#------------------------------------------------------------------------------ #$Date: 2013-12-29 11:49:26 +0000 (Sun, 29 Dec 2013) $ #$Revision: 91935 $ #$URL: svn://www.crystallography.net/cod/cif/4/00/07/4000708.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_4000708 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_volume 23 _journal_year 2011 _chemical_formula_moiety 'C23 H25 N9' _chemical_formula_sum 'C23 H25 N9' _chemical_formula_weight 427.51 _space_group_IT_number 14 _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 geom _atom_sites_solution_primary direct _audit_creation_date 09-05-20 _audit_creation_method CRYSTALS_ver_12.86 _cell_angle_alpha 90 _cell_angle_beta 106.259(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.920(5) _cell_length_b 14.000(5) _cell_length_c 15.753(5) _cell_measurement_reflns_used 0 _cell_measurement_temperature 293 _cell_measurement_theta_max 0 _cell_measurement_theta_min 0 _cell_volume 2312.0(15) _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 0.996 _diffrn_measured_fraction_theta_max 0.891 _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 0.175 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 25229 _diffrn_reflns_theta_full 26.428 _diffrn_reflns_theta_max 29.365 _diffrn_reflns_theta_min 3.197 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.079 _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 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 904 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.79 _refine_diff_density_min -0.72 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.1518 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 5650 _refine_ls_number_restraints 62 _refine_ls_R_factor_all 0.1901 _refine_ls_R_factor_gt 0.1265 _refine_ls_shift/su_max 0.053728 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.20P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.3538 _refine_ls_wR_factor_gt 0.3209 _refine_ls_wR_factor_ref 0.3538 _reflns_limit_h_max 14 _reflns_limit_h_min -14 _reflns_limit_k_max 18 _reflns_limit_k_min 0 _reflns_limit_l_max 21 _reflns_limit_l_min 0 _reflns_number_gt 2344 _reflns_number_total 5664 _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 0.1901 _oxford_refine_ls_scale 4.3(2) _oxford_reflns_number_all 5650 _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _oxford_structure_analysis_title 'jm114a in P 1 21/c 1' _[local]_cod_data_source_file cm102165r_si_007.cif _[local]_cod_data_source_block JMdiazide _[local]_cod_cif_authors_sg_H-M 'P 1 21/c 1 ' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_database_code 4000708 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 C1 C 0.7164(3) 0.4634(2) 0.0233(2) 0.0536 1.0000 Uani . . C2 C 1.0604(3) 0.8002(2) -0.0323(3) 0.0546 1.0000 Uani . . C3 C 0.5224(4) 0.3240(3) -0.0036(3) 0.0646 1.0000 Uani . . C4 C 1.0466(3) 0.6570(2) 0.0964(3) 0.0568 1.0000 Uani . U C5 C 0.9484(3) 0.6652(2) 0.0090(3) 0.0543 1.0000 Uani . . C6 C 1.0594(4) 0.8750(3) -0.0873(3) 0.0638 1.0000 Uani . . C7 C 0.8411(3) 0.5999(2) -0.0131(3) 0.0549 1.0000 Uani . . N8 N 0.4296(4) 0.2533(3) -0.0175(3) 0.0880 1.0000 Uani D U C9 C 0.8197(4) 0.5325(2) 0.0406(3) 0.0595 1.0000 Uani . . C10 C 0.5292(4) 0.3854(3) -0.0707(3) 0.0614 1.0000 Uani . . C11 C 0.9580(3) 0.7333(2) -0.0487(3) 0.0585 1.0000 Uani . . C12 C 1.1233(3) 0.7488(2) 0.1257(3) 0.0592 1.0000 Uani . . C13 C 0.6234(4) 0.4542(2) -0.0567(3) 0.0599 1.0000 Uani . . C14 C 1.1678(3) 0.7860(3) 0.0499(3) 0.0651 1.0000 Uani . U C16 C 0.7079(4) 0.4029(3) 0.0896(3) 0.0747 1.0000 Uani . . C17 C 0.6122(5) 0.3350(3) 0.0772(3) 0.0843 1.0000 Uani . . C20 C 1.2384(4) 0.7250(3) 0.2052(3) 0.0803 1.0000 Uani . U C26 C 1.0422(4) 0.8210(3) 0.1572(4) 0.0815 1.0000 Uani . U C15 C 0.3378(4) 0.2375(3) -0.1017(3) 0.0788 1.0000 Uani . U N4 N 0.2264(5) 0.0966(3) -0.2491(3) 0.1030 1.0000 Uani . . N5 N 0.8787(5) 0.8993(3) -0.2286(3) 0.1022 1.0000 Uani . U N6 N 0.4568(7) 0.1088(5) 0.1876(4) 0.1608 1.0000 Uani . U N7 N 0.3023(6) 0.1594(4) -0.2443(3) 0.1271 1.0000 Uani . U C18 C 0.3921(5) 0.1781(4) -0.1616(5) 0.1056 1.0000 Uani . U N9 N 1.2397(5) 0.9999(3) -0.0514(4) 0.1213 1.0000 Uani . U N18 N 0.1503(7) 0.0411(5) -0.2657(4) 0.1427 1.0000 Uani . U N32 N 0.4100(5) 0.0365(4) 0.1860(4) 0.1098 1.0000 Uani . . C21 C 0.9599(5) 0.8888(3) -0.1661(3) 0.0732 1.0000 Uani . U C8 C 1.1611(4) 0.9439(3) -0.0671(4) 0.0845 1.0000 Uani . U N1 N 0.3677(7) -0.0309(5) 0.1982(5) 0.1486 1.0000 Uani . U C23 C 0.4734(7) 0.1466(6) 0.0694(6) 0.1496 1.0000 Uani D U C24 C 0.3994(6) 0.2033(6) 0.0830(6) 0.1528 1.0000 Uani D U H41 H 1.1075 0.6075 0.0919 0.0391 1.0000 Uiso R . H42 H 1.0037 0.6386 0.1396 0.0391 1.0000 Uiso R . H71 H 0.7806 0.6083 -0.0708 0.0335 1.0000 Uiso R . H91 H 0.8790 0.5285 0.0937 0.0360 1.0000 Uiso R . H101 H 0.4702 0.3811 -0.1267 0.0433 1.0000 Uiso R . H111 H 0.8931 0.7385 -0.1009 0.0359 1.0000 Uiso R . H131 H 0.6246 0.4955 -0.1043 0.0403 1.0000 Uiso R . H141 H 1.2111 0.8467 0.0673 0.0483 1.0000 Uiso R . H142 H 1.2270 0.7409 0.0366 0.0482 1.0000 Uiso R . H161 H 0.7646 0.4087 0.1470 0.0555 1.0000 Uiso R . H171 H 0.6093 0.2957 0.1253 0.0642 1.0000 Uiso R . H203 H 1.2764 0.7825 0.2353 0.0731 1.0000 Uiso R . H202 H 1.3006 0.6916 0.1811 0.0732 1.0000 Uiso R . H201 H 1.2141 0.6844 0.2476 0.0733 1.0000 Uiso R . H261 H 1.0952 0.8690 0.1927 0.0770 1.0000 Uiso R . H262 H 0.9816 0.8510 0.1079 0.0774 1.0000 Uiso R . H263 H 0.9948 0.7906 0.1938 0.0769 1.0000 Uiso R . H181 H 0.4686 0.2065 -0.1690 0.0849 1.0000 Uiso R . H182 H 0.4153 0.1168 -0.1337 0.0849 1.0000 Uiso R . H151 H 0.3116 0.2965 -0.1325 0.0676 1.0000 Uiso R . H152 H 0.2633 0.2066 -0.0941 0.0676 1.0000 Uiso R . H241 H 0.4192 0.2435 0.1334 0.1118 1.0000 Uiso R . H242 H 0.3117 0.1809 0.0739 0.1118 1.0000 Uiso R . H231 H 0.5567 0.1623 0.0747 0.1092 1.0000 Uiso R . H232 H 0.4466 0.0934 0.0292 0.1092 1.0000 Uiso R . 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 0.0561(19) 0.0470(18) 0.050(2) -0.0032(16) 0.0027(17) -0.0149(15) C2 0.0495(19) 0.0486(19) 0.059(2) -0.0011(17) 0.0041(17) -0.0081(15) C3 0.059(2) 0.058(2) 0.066(3) 0.0035(18) 0.0001(19) -0.0248(17) C4 0.056(2) 0.0459(18) 0.061(2) 0.0004(16) 0.0058(18) -0.0121(15) C5 0.0505(19) 0.0402(17) 0.064(2) -0.0061(16) 0.0030(17) -0.0093(14) C6 0.057(2) 0.054(2) 0.072(3) 0.005(2) 0.004(2) -0.0149(17) C7 0.056(2) 0.0455(18) 0.053(2) -0.0027(16) -0.0011(17) -0.0152(15) N8 0.091(2) 0.088(2) 0.073(2) 0.0123(19) 0.003(2) -0.052(2) C9 0.057(2) 0.0495(19) 0.061(2) -0.0049(17) -0.0021(18) -0.0124(16) C10 0.057(2) 0.056(2) 0.058(2) 0.0005(18) -0.0058(18) -0.0125(17) C11 0.054(2) 0.0495(19) 0.058(2) 0.0021(17) -0.0070(17) -0.0130(16) C12 0.056(2) 0.0489(19) 0.061(2) -0.0046(17) -0.0032(18) -0.0093(16) C13 0.066(2) 0.048(2) 0.059(2) 0.0049(17) 0.0076(19) -0.0131(16) C14 0.0478(19) 0.052(2) 0.086(3) 0.0011(19) 0.003(2) -0.0133(16) C16 0.078(3) 0.073(3) 0.055(2) 0.010(2) -0.012(2) -0.034(2) C17 0.091(3) 0.082(3) 0.061(3) 0.018(2) -0.010(2) -0.044(2) C20 0.066(2) 0.076(3) 0.078(3) 0.006(2) -0.013(2) -0.016(2) C26 0.071(3) 0.064(2) 0.101(3) -0.018(2) 0.011(2) -0.011(2) C15 0.056(2) 0.078(3) 0.096(3) -0.001(2) 0.011(2) -0.029(2) N4 0.131(4) 0.088(3) 0.085(3) -0.020(2) 0.021(3) -0.037(3) N5 0.101(3) 0.093(3) 0.094(3) 0.028(2) -0.003(3) -0.013(2) N6 0.188(5) 0.153(5) 0.108(4) 0.034(3) -0.013(4) -0.097(4) N7 0.165(5) 0.114(4) 0.087(3) -0.015(3) 0.011(3) -0.074(3) C18 0.086(3) 0.092(3) 0.134(5) -0.026(3) 0.024(3) -0.033(3) N9 0.111(3) 0.100(3) 0.125(4) 0.032(3) -0.012(3) -0.053(3) N18 0.164(4) 0.134(4) 0.123(4) -0.016(3) 0.028(4) -0.071(4) N32 0.128(4) 0.086(3) 0.116(4) -0.001(3) 0.035(3) -0.041(3) C21 0.075(3) 0.060(2) 0.076(3) 0.018(2) 0.008(2) -0.012(2) C8 0.076(3) 0.064(2) 0.099(3) 0.021(2) 0.002(3) -0.023(2) N1 0.166(5) 0.117(4) 0.164(5) -0.001(4) 0.049(4) -0.037(4) C23 0.090(4) 0.135(5) 0.224(7) -0.098(5) 0.045(4) -0.049(4) C24 0.074(3) 0.132(5) 0.225(7) -0.073(5) -0.003(4) -0.022(4) 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 C13 124.4(3) yes C9 C1 C16 119.0(3) yes C13 C1 C16 116.6(3) yes C6 C2 C11 121.8(3) yes C6 C2 C14 121.3(3) yes C11 C2 C14 116.9(3) yes N8 C3 C10 121.1(4) yes N8 C3 C17 121.6(4) yes C10 C3 C17 117.3(3) yes C5 C4 C12 113.8(3) yes C5 C4 H41 108.3 no C12 C4 H41 106.9 no C5 C4 H42 107.9 no C12 C4 H42 110.1 no H41 C4 H42 109.8 no C4 C5 C7 119.7(3) yes C4 C5 C11 120.5(3) yes C7 C5 C11 119.8(3) yes C2 C6 C21 122.2(3) yes C2 C6 C8 120.6(4) yes C21 C6 C8 117.3(3) yes C5 C7 C9 124.6(4) yes C5 C7 H71 116.2 no C9 C7 H71 119.2 no C3 N8 C15 123.0(3) yes C3 N8 C24 115.7(4) yes C15 N8 C24 119.1(3) yes C1 C9 C7 128.2(4) yes C1 C9 H91 116.7 no C7 C9 H91 115.1 no C3 C10 C13 120.7(4) yes C3 C10 H101 120.6 no C13 C10 H101 118.7 no C2 C11 C5 123.4(3) yes C2 C11 H111 118.3 no C5 C11 H111 118.2 no C4 C12 C14 108.8(3) yes C4 C12 C20 108.4(3) yes C14 C12 C20 110.4(3) yes C4 C12 C26 109.7(3) yes C14 C12 C26 112.2(3) yes C20 C12 C26 107.2(4) yes C1 C13 C10 122.2(3) yes C1 C13 H131 119.5 no C10 C13 H131 118.3 no C12 C14 C2 112.6(3) yes C12 C14 H141 108.6 no C2 C14 H141 109.2 no C12 C14 H142 109.3 no C2 C14 H142 108.0 no H141 C14 H142 109.2 no C1 C16 C17 121.8(4) yes C1 C16 H161 120.7 no C17 C16 H161 117.4 no C16 C17 C3 121.3(4) yes C16 C17 H171 118.7 no C3 C17 H171 120.0 no C12 C20 H203 111.0 no C12 C20 H202 106.4 no H203 C20 H202 109.6 no C12 C20 H201 111.7 no H203 C20 H201 108.3 no H202 C20 H201 109.8 no C12 C26 H261 110.2 no C12 C26 H262 111.0 no H261 C26 H262 109.2 no C12 C26 H263 111.1 no H261 C26 H263 107.2 no H262 C26 H263 108.0 no N8 C15 C18 111.7(4) yes N8 C15 H151 111.5 no C18 C15 H151 105.8 no N8 C15 H152 110.6 no C18 C15 H152 109.1 no H151 C15 H152 107.9 no N7 N4 N18 170.3(6) yes N4 N7 C18 118.9(5) yes C15 C18 N7 112.7(5) yes C15 C18 H181 110.9 no N7 C18 H181 111.5 no C15 C18 H182 107.8 no N7 C18 H182 106.3 no H181 C18 H182 107.3 no N6 N32 N1 168.8(7) yes C6 C21 N5 178.8(5) yes C6 C8 N9 178.6(5) yes C24 C23 H231 121.9 no C24 C23 H232 122.2 no H231 C23 H232 110.7 no N8 C24 C23 78.8(7) yes N8 C24 H241 116.2 no C23 C24 H241 122.5 no N8 C24 H242 113.5 no C23 C24 H242 116.4 no H241 C24 H242 107.3 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C9 1.452(5) yes C1 C13 1.386(5) yes C1 C16 1.367(5) yes C2 C6 1.357(5) yes C2 C11 1.426(4) yes C2 C14 1.498(5) yes C3 N8 1.389(5) yes C3 C10 1.380(5) yes C3 C17 1.381(6) yes C4 C5 1.494(5) yes C4 C12 1.534(5) yes C4 H41 0.977 no C4 H42 0.962 no C5 C7 1.450(5) yes C5 C11 1.341(5) yes C6 C21 1.415(6) yes C6 C8 1.438(5) yes C7 C9 1.332(5) yes C7 H71 0.970 no N8 C15 1.438(6) yes N8 C24 1.844(10) yes C9 H91 0.905 no C10 C13 1.381(5) yes C10 H101 0.938 no C11 H111 0.926 no C12 C14 1.503(6) yes C12 C20 1.542(6) yes C12 C26 1.515(6) yes C13 H131 0.949 no C14 H141 0.974 no C14 H142 0.968 no C16 C17 1.385(5) yes C16 H161 0.946 no C17 H171 0.944 no C20 H203 0.967 no C20 H202 0.986 no C20 H201 0.970 no C26 H261 0.958 no C26 H262 0.964 no C26 H263 0.974 no C15 C18 1.500(7) yes C15 H151 0.960 no C15 H152 0.958 no N4 N7 1.196(6) yes N4 N18 1.114(6) yes N5 C21 1.136(6) yes N6 N32 1.130(6) yes N7 C18 1.419(7) yes C18 H181 0.960 no C18 H182 0.966 no N9 C8 1.137(5) yes N32 N1 1.092(6) yes C23 C24 1.194(8) yes C23 H231 0.916 no C23 H232 0.969 no C24 H241 0.947 no C24 H242 0.979 no _journal_paper_doi 10.1021/cm102165r