#------------------------------------------------------------------------------ #$Date: 2025-08-19 20:30:04 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301811 $ #$URL: svn://www.crystallography.net/cod/cif/4/00/07/4000710.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_4000710 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 H25 Cl2 N3' _chemical_formula_sum 'C23 H25 Cl2 N3' _chemical_formula_weight 414.38 _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 09-05-26 _audit_creation_method CRYSTALS_ver_12.85 _cell_angle_alpha 70.273(5) _cell_angle_beta 70.515(5) _cell_angle_gamma 65.327(5) _cell_formula_units_Z 2 _cell_length_a 9.244(5) _cell_length_b 10.877(5) _cell_length_c 13.234(5) _cell_measurement_reflns_used 0 _cell_measurement_temperature 293 _cell_measurement_theta_max 0 _cell_measurement_theta_min 0 _cell_volume 1108.9(9) _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 0.990 _diffrn_measured_fraction_theta_max 0.812 _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 0.041 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 8519 _diffrn_reflns_theta_full 25.118 _diffrn_reflns_theta_max 29.550 _diffrn_reflns_theta_min 3.301 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.306 _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 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 436 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.86 _refine_diff_density_min -0.63 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.8807 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 5044 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1061 _refine_ls_R_factor_gt 0.0753 _refine_ls_shift/su_max 0.000136 _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 0.2491 _refine_ls_wR_factor_gt 0.2331 _refine_ls_wR_factor_ref 0.2491 _reflns_limit_h_max 12 _reflns_limit_h_min -11 _reflns_limit_k_max 14 _reflns_limit_k_min -13 _reflns_limit_l_max 16 _reflns_limit_l_min 0 _reflns_number_gt 2819 _reflns_number_total 5052 _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 0.1061 _oxford_refine_ls_scale 6.4(3) _oxford_reflns_number_all 5044 _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _oxford_structure_analysis_title 'jm114c in P -1' _cod_data_source_file cm102165r_si_009.cif _cod_data_source_block JMdiCl _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 4000710 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 Cl1 Cl -0.41414(12) 0.53726(11) 0.32246(9) 0.0870 1.0000 Uani Cl2 Cl 0.19735(15) 0.80060(12) 0.19579(10) 0.1002 1.0000 Uani C3 C 0.0256(3) 0.4448(2) 0.1989(2) 0.0429 1.0000 Uani C4 C 0.4298(3) 0.0353(2) -0.1539(2) 0.0410 1.0000 Uani C5 C 0.1280(3) 0.4723(2) 0.0952(2) 0.0449 1.0000 Uani N6 N -0.0470(3) 0.5399(2) 0.26383(18) 0.0481 1.0000 Uani C7 C 0.2017(3) 0.3779(3) 0.0300(2) 0.0458 1.0000 Uani C8 C 0.5428(3) 0.0444(2) -0.2504(2) 0.0431 1.0000 Uani C9 C 0.3630(3) 0.1445(3) -0.0960(2) 0.0431 1.0000 Uani C10 C 0.6153(3) -0.0603(2) -0.3115(2) 0.0439 1.0000 Uani C11 C -0.0125(4) 0.6679(3) 0.2298(2) 0.0509 1.0000 Uani C12 C 0.0767(3) 0.2233(3) 0.1668(2) 0.0457 1.0000 Uani C13 C 0.2546(3) 0.1437(3) 0.0009(2) 0.0452 1.0000 Uani C14 C 0.1805(3) 0.2491(2) 0.0642(2) 0.0423 1.0000 Uani C15 C 0.0001(3) 0.3174(3) 0.2327(2) 0.0476 1.0000 Uani C16 C 0.3778(4) -0.0892(3) -0.1080(2) 0.0506 1.0000 Uani C17 C 0.7218(4) -0.0443(3) -0.4108(2) 0.0503 1.0000 Uani C18 C -0.1373(4) 0.5081(3) 0.3773(2) 0.0560 1.0000 Uani C19 C 0.4014(3) -0.1658(3) -0.1924(2) 0.0493 1.0000 Uani C20 C 0.5743(3) -0.1908(3) -0.2630(2) 0.0490 1.0000 Uani C21 C 0.1487(4) 0.6457(3) 0.2524(3) 0.0624 1.0000 Uani C22 C 0.7928(4) -0.1493(3) -0.4726(2) 0.0620 1.0000 Uani C23 C 0.7683(4) 0.0763(3) -0.4597(2) 0.0648 1.0000 Uani N24 N 0.8467(5) -0.2338(3) -0.5202(3) 0.0888 1.0000 Uani C25 C 0.3772(5) -0.3062(3) -0.1334(3) 0.0731 1.0000 Uani N26 N 0.8025(5) 0.1735(3) -0.4990(3) 0.0957 1.0000 Uani C27 C -0.3195(4) 0.5850(4) 0.3938(3) 0.0687 1.0000 Uani C28 C 0.2763(4) -0.0806(4) -0.2640(3) 0.0729 1.0000 Uani H51 H 0.1405 0.5608 0.0676 0.0533 1.0000 Uiso H71 H 0.2705 0.4005 -0.0388 0.0515 1.0000 Uiso H81 H 0.5750 0.1179 -0.2778 0.0521 1.0000 Uiso H91 H 0.4029 0.2170 -0.1265 0.0531 1.0000 Uiso H112 H -0.1017 0.7383 0.2691 0.0634 1.0000 Uiso H111 H -0.0131 0.7111 0.1511 0.0628 1.0000 Uiso H121 H 0.0619 0.1307 0.1952 0.0561 1.0000 Uiso H131 H 0.2170 0.0663 0.0319 0.0555 1.0000 Uiso H151 H -0.0690 0.2938 0.3004 0.0556 1.0000 Uiso H161 H 0.4381 -0.1541 -0.0512 0.0640 1.0000 Uiso H162 H 0.2610 -0.0600 -0.0719 0.0652 1.0000 Uiso H181 H -0.0954 0.5386 0.4238 0.0639 1.0000 Uiso H182 H -0.1155 0.4072 0.4033 0.0640 1.0000 Uiso H202 H 0.5841 -0.2306 -0.3211 0.0576 1.0000 Uiso H201 H 0.6488 -0.2603 -0.2153 0.0569 1.0000 Uiso H211 H 0.1476 0.6187 0.3334 0.0778 1.0000 Uiso H212 H 0.2407 0.5759 0.2144 0.0768 1.0000 Uiso H251 H 0.3960 -0.3620 -0.1852 0.1183 1.0000 Uiso H252 H 0.4499 -0.3599 -0.0847 0.1175 1.0000 Uiso H253 H 0.2723 -0.2983 -0.0868 0.1172 1.0000 Uiso H271 H -0.3341 0.6898 0.3622 0.0785 1.0000 Uiso H272 H -0.3757 0.5724 0.4786 0.0798 1.0000 Uiso H282 H 0.2923 -0.1344 -0.3166 0.1137 1.0000 Uiso H281 H 0.2916 0.0077 -0.3070 0.1141 1.0000 Uiso H283 H 0.1648 -0.0585 -0.2227 0.1151 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 Cl1 0.0834(7) 0.0945(7) 0.0861(7) -0.0168(6) -0.0101(5) -0.0436(6) Cl2 0.1288(9) 0.0964(8) 0.1030(8) -0.0066(6) -0.0237(7) -0.0793(7) C3 0.0475(14) 0.0373(12) 0.0403(13) -0.0120(10) -0.0038(10) -0.0136(11) C4 0.0503(14) 0.0395(12) 0.0388(13) -0.0110(10) -0.0123(11) -0.0173(11) C5 0.0588(15) 0.0323(11) 0.0409(14) -0.0099(10) -0.0034(11) -0.0179(11) N6 0.0594(13) 0.0420(11) 0.0431(12) -0.0179(10) 0.0019(10) -0.0219(10) C7 0.0548(15) 0.0437(14) 0.0346(12) -0.0096(11) -0.0016(11) -0.0191(12) C8 0.0577(15) 0.0366(12) 0.0380(13) -0.0131(10) -0.0032(11) -0.0215(11) C9 0.0538(15) 0.0420(13) 0.0398(13) -0.0145(11) -0.0074(11) -0.0208(12) C10 0.0580(16) 0.0382(12) 0.0362(13) -0.0101(10) -0.0116(11) -0.0154(12) C11 0.0645(17) 0.0378(13) 0.0489(15) -0.0160(12) -0.0040(13) -0.0182(12) C12 0.0518(15) 0.0417(13) 0.0450(14) -0.0159(11) 0.0027(11) -0.0235(12) C13 0.0527(15) 0.0432(13) 0.0433(14) -0.0173(11) -0.0044(11) -0.0190(12) C14 0.0465(14) 0.0399(13) 0.0415(13) -0.0150(11) -0.0059(11) -0.0145(11) C15 0.0539(15) 0.0448(14) 0.0437(14) -0.0163(11) 0.0058(11) -0.0249(12) C16 0.0626(17) 0.0502(14) 0.0435(14) -0.0175(12) 0.0020(12) -0.0294(13) C17 0.0691(18) 0.0427(13) 0.0361(13) -0.0131(11) -0.0035(12) -0.0199(13) C18 0.0711(19) 0.0474(15) 0.0445(15) -0.0173(12) 0.0014(13) -0.0217(14) C19 0.0643(17) 0.0476(14) 0.0460(15) -0.0137(12) -0.0070(12) -0.0305(13) C20 0.0657(17) 0.0402(13) 0.0439(14) -0.0153(11) -0.0078(12) -0.0197(13) C21 0.075(2) 0.0573(17) 0.0599(19) -0.0139(14) -0.0104(15) -0.0312(16) C22 0.089(2) 0.0509(16) 0.0422(15) -0.0169(13) -0.0052(14) -0.0235(16) C23 0.089(2) 0.0591(18) 0.0415(15) -0.0192(14) 0.0076(15) -0.0322(17) N24 0.125(3) 0.0748(19) 0.0630(18) -0.0382(16) -0.0015(18) -0.0287(19) C25 0.100(3) 0.0622(19) 0.073(2) -0.0202(17) -0.0024(19) -0.0527(19) N26 0.142(3) 0.075(2) 0.068(2) -0.0145(16) 0.0185(19) -0.069(2) C27 0.074(2) 0.0699(19) 0.0593(19) -0.0296(16) 0.0103(15) -0.0299(17) C28 0.079(2) 0.074(2) 0.082(2) -0.0178(18) -0.0318(18) -0.0317(19) 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 '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 C5 C3 N6 121.1(2) yes C5 C3 C15 117.0(2) yes N6 C3 C15 121.9(2) yes C8 C4 C9 119.8(2) yes C8 C4 C16 119.6(2) yes C9 C4 C16 120.6(2) yes C3 C5 C7 121.6(2) yes C3 C5 H51 118.9 no C7 C5 H51 119.4 no C3 N6 C11 121.0(2) yes C3 N6 C18 122.5(2) yes C11 N6 C18 115.6(2) yes C5 C7 C14 121.8(2) yes C5 C7 H71 118.6 no C14 C7 H71 119.6 no C4 C8 C10 122.9(2) yes C4 C8 H81 120.0 no C10 C8 H81 117.1 no C4 C9 C13 124.5(2) yes C4 C9 H91 116.9 no C13 C9 H91 118.6 no C8 C10 C17 121.2(2) yes C8 C10 C20 118.4(2) yes C17 C10 C20 120.4(2) yes N6 C11 C21 111.9(2) yes N6 C11 H112 110.2 no C21 C11 H112 108.8 no N6 C11 H111 110.9 no C21 C11 H111 110.5 no H112 C11 H111 104.2 no C14 C12 C15 122.7(2) yes C14 C12 H121 118.5 no C15 C12 H121 118.7 no C9 C13 C14 128.1(2) yes C9 C13 H131 117.1 no C14 C13 H131 114.8 no C13 C14 C7 125.2(2) yes C13 C14 C12 118.5(2) yes C7 C14 C12 116.3(2) yes C3 C15 C12 120.6(2) yes C3 C15 H151 121.1 no C12 C15 H151 118.3 no C4 C16 C19 114.9(2) yes C4 C16 H161 108.9 no C19 C16 H161 109.0 no C4 C16 H162 109.0 no C19 C16 H162 107.5 no H161 C16 H162 107.4 no C10 C17 C22 121.0(2) yes C10 C17 C23 122.8(2) yes C22 C17 C23 116.2(2) yes N6 C18 C27 113.9(3) yes N6 C18 H181 106.9 no C27 C18 H181 107.2 no N6 C18 H182 110.0 no C27 C18 H182 109.8 no H181 C18 H182 109.0 no C16 C19 C20 108.6(2) yes C16 C19 C25 109.7(2) yes C20 C19 C25 109.3(2) yes C16 C19 C28 110.1(2) yes C20 C19 C28 110.6(2) yes C25 C19 C28 108.5(2) yes C19 C20 C10 112.6(2) yes C19 C20 H202 107.8 no C10 C20 H202 109.9 no C19 C20 H201 106.9 no C10 C20 H201 111.0 no H202 C20 H201 108.5 no C11 C21 Cl2 110.4(2) yes C11 C21 H211 113.4 no Cl2 C21 H211 106.8 no C11 C21 H212 111.0 no Cl2 C21 H212 104.6 no H211 C21 H212 110.2 no C17 C22 N24 178.5(4) yes C17 C23 N26 178.7(4) yes C19 C25 H251 112.8 no C19 C25 H252 110.5 no H251 C25 H252 108.2 no C19 C25 H253 113.7 no H251 C25 H253 107.4 no H252 C25 H253 103.8 no C18 C27 Cl1 113.0(2) yes C18 C27 H271 106.0 no Cl1 C27 H271 108.6 no C18 C27 H272 110.5 no Cl1 C27 H272 111.4 no H271 C27 H272 107.1 no C19 C28 H282 108.3 no C19 C28 H281 111.4 no H282 C28 H281 107.7 no C19 C28 H283 113.7 no H282 C28 H283 108.7 no H281 C28 H283 106.8 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C27 1.786(4) yes Cl2 C21 1.778(3) yes C3 C5 1.400(3) yes C3 N6 1.377(3) yes C3 C15 1.400(3) yes C4 C8 1.358(3) yes C4 C9 1.437(3) yes C4 C16 1.492(3) yes C5 C7 1.373(3) yes C5 H51 0.949 no N6 C11 1.447(3) yes N6 C18 1.458(3) yes C7 C14 1.396(3) yes C7 H71 0.942 no C8 C10 1.422(3) yes C8 H81 0.889 no C9 C13 1.338(4) yes C9 H91 0.922 no C10 C17 1.361(4) yes C10 C20 1.497(3) yes C11 C21 1.522(5) yes C11 H112 0.996 no C11 H111 0.988 no C12 C14 1.393(3) yes C12 C15 1.376(4) yes C12 H121 1.000 no C13 C14 1.447(3) yes C13 H131 0.955 no C15 H151 0.937 no C16 C19 1.518(4) yes C16 H161 0.983 no C16 H162 0.984 no C17 C22 1.432(4) yes C17 C23 1.427(4) yes C18 C27 1.511(5) yes C18 H181 1.022 no C18 H182 0.985 no C19 C20 1.521(4) yes C19 C25 1.534(4) yes C19 C28 1.529(4) yes C20 H202 0.967 no C20 H201 0.988 no C21 H211 1.008 no C21 H212 0.993 no C22 N24 1.136(4) yes C23 N26 1.135(4) yes C25 H251 0.991 no C25 H252 0.957 no C25 H253 0.947 no C27 H271 1.039 no C27 H272 1.056 no C28 H282 0.991 no C28 H281 0.978 no C28 H283 0.961 no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30656415 2 PubChem 139080301