#------------------------------------------------------------------------------ #$Date: 2013-12-29 11:49:26 +0000 (Sun, 29 Dec 2013) $ #$Revision: 91935 $ #$URL: svn://www.crystallography.net/cod/cif/4/00/07/4000709.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_4000709 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 H26 Cl1 N3' _chemical_formula_sum 'C23 H26 Cl N3' _chemical_formula_weight 379.93 _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 09-05-13 _audit_creation_method CRYSTALS_ver_12.85 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.7228(18) _cell_length_b 11.5429(12) _cell_length_c 23.123(3) _cell_measurement_reflns_used 0 _cell_measurement_temperature 293 _cell_measurement_theta_max 0 _cell_measurement_theta_min 0 _cell_volume 4196.5(8) _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 0.71073 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 25330 _diffrn_reflns_theta_full 26.550 _diffrn_reflns_theta_max 29.500 _diffrn_reflns_theta_min 3.257 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.194 _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 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1616 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.84 _refine_diff_density_min -0.80 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.8155 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 244 _refine_ls_number_reflns 5194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1447 _refine_ls_R_factor_gt 0.0553 _refine_ls_shift/su_max 0.104303 _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: 542. 719. 238. 0.00 -14.4 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1472 _refine_ls_wR_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1472 _reflns_limit_h_max 21 _reflns_limit_h_min 0 _reflns_limit_k_max 15 _reflns_limit_k_min 0 _reflns_limit_l_max 29 _reflns_limit_l_min 0 _reflns_number_gt 2017 _reflns_number_total 5202 _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 0.1447 _oxford_refine_ls_scale 2.153(15) _oxford_reflns_number_all 5194 _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _oxford_structure_analysis_title 'jmcl in P b c a' _[local]_cod_data_source_file cm102165r_si_008.cif _[local]_cod_data_source_block JMCl _[local]_cod_cif_authors_sg_H-M 'P b c a ' _[local]_cod_chemical_formula_sum_orig 'C23 H26 Cl1 N3' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_cell_volume 4196.6(9) _cod_database_code 4000709 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-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 Cl1 Cl 0.21874(9) 1.00354(15) 0.29509(6) 0.0855 1.0000 Uani C2 C 0.1046(3) 0.2664(4) 0.01506(17) 0.0431 1.0000 Uani C3 C 0.1665(3) 0.0767(4) -0.05457(17) 0.0429 1.0000 Uani C4 C 0.0977(3) 0.5254(3) 0.11945(16) 0.0410 1.0000 Uani C5 C 0.0737(3) 0.1077(3) -0.05191(17) 0.0407 1.0000 Uani C6 C 0.0144(3) 0.5645(4) 0.12553(18) 0.0457 1.0000 Uani C7 C 0.2250(2) 0.1797(4) -0.04277(18) 0.0425 1.0000 Uani C8 C 0.1235(3) 0.4298(4) 0.08344(18) 0.0439 1.0000 Uani C9 C 0.0494(3) 0.2033(4) -0.01649(18) 0.0438 1.0000 Uani N10 N 0.0343(3) 0.8077(4) 0.22768(19) 0.0733 1.0000 Uani C11 C 0.1586(3) 0.5847(4) 0.1514(2) 0.0557 1.0000 Uani C12 C 0.0163(3) 0.0412(4) -0.08145(18) 0.0439 1.0000 Uani C13 C 0.0750(3) 0.3610(4) 0.04993(19) 0.0459 1.0000 Uani N14 N -0.1442(3) 0.0789(4) -0.0792(2) 0.0760 1.0000 Uani C15 C 0.0413(3) -0.0556(4) -0.1149(2) 0.0585 1.0000 Uani C16 C 0.0550(3) 0.7141(4) 0.19320(19) 0.0509 1.0000 Uani C17 C -0.0066(3) 0.6547(4) 0.16159(18) 0.0476 1.0000 Uani C18 C 0.3163(3) 0.1354(5) -0.0372(2) 0.0650 1.0000 Uani C19 C -0.0732(3) 0.0639(4) -0.0798(2) 0.0540 1.0000 Uani C20 C 0.1976(3) 0.2370(4) 0.01349(19) 0.0506 1.0000 Uani C21 C 0.2205(3) 0.2671(4) -0.0924(2) 0.0561 1.0000 Uani N22 N 0.0609(3) -0.1336(5) -0.1414(2) 0.0961 1.0000 Uani C23 C 0.1392(3) 0.6752(5) 0.1872(2) 0.0667 1.0000 Uani C24 C -0.1056(4) 0.7830(5) 0.2759(3) 0.0849 1.0000 Uani C25 C -0.0531(3) 0.8508(4) 0.2332(2) 0.0659 1.0000 Uani C26 C 0.1391(5) 0.9432(5) 0.2423(3) 0.1015 1.0000 Uani C27 C 0.1005(5) 0.8536(5) 0.2736(2) 0.0863 1.0000 Uani H61 H -0.0303 0.5288 0.1046 0.0531 1.0000 Uiso H81 H 0.1816 0.4109 0.0832 0.0519 1.0000 Uiso H111 H 0.2154 0.5609 0.1484 0.0651 1.0000 Uiso H131 H 0.0164 0.3765 0.0499 0.0530 1.0000 Uiso H171 H -0.0635 0.6778 0.1640 0.0559 1.0000 Uiso H181 H 0.3525 0.2001 -0.0319 0.0971 1.0000 Uiso H182 H 0.3313 0.0968 -0.0729 0.0970 1.0000 Uiso H183 H 0.3212 0.0815 -0.0050 0.0966 1.0000 Uiso H212 H 0.2620 0.3251 -0.0847 0.0839 1.0000 Uiso H211 H 0.2323 0.2279 -0.1283 0.0842 1.0000 Uiso H213 H 0.1654 0.3025 -0.0930 0.0841 1.0000 Uiso H231 H 0.1821 0.7102 0.2077 0.0793 1.0000 Uiso H241 H -0.1596 0.8222 0.2812 0.1232 1.0000 Uiso H243 H -0.0768 0.7838 0.3133 0.1230 1.0000 Uiso H242 H -0.1137 0.7030 0.2636 0.1233 1.0000 Uiso H251 H -0.0509 0.9313 0.2477 0.0782 1.0000 Uiso H252 H -0.0813 0.8510 0.1949 0.0780 1.0000 Uiso H261 H 0.0972 1.0020 0.2317 0.1228 1.0000 Uiso H262 H 0.1666 0.9136 0.2078 0.1229 1.0000 Uiso H272 H 0.0719 0.8841 0.3089 0.1040 1.0000 Uiso H271 H 0.1427 0.7954 0.2859 0.1041 1.0000 Uiso H32 H 0.1800 0.0439 -0.0938 0.0508 1.0000 Uiso H31 H 0.1788 0.0143 -0.0251 0.0504 1.0000 Uiso H91 H -0.0106 0.2227 -0.0155 0.0520 1.0000 Uiso H201 H 0.2308 0.3101 0.0175 0.0626 1.0000 Uiso H202 H 0.2103 0.1842 0.0468 0.0627 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 0.0828(9) 0.0863(10) 0.0872(10) -0.0198(9) -0.0210(8) -0.0152(9) C2 0.043(2) 0.043(2) 0.044(2) -0.0098(18) 0.0040(19) -0.0034(19) C3 0.043(2) 0.039(2) 0.046(2) -0.0028(18) 0.0048(19) 0.0005(18) C4 0.049(2) 0.040(2) 0.034(2) -0.0039(17) -0.0012(17) -0.0028(19) C5 0.042(2) 0.041(2) 0.040(2) 0.0016(17) 0.0088(17) -0.0058(18) C6 0.046(2) 0.050(2) 0.042(2) -0.0106(19) -0.0038(19) -0.005(2) C7 0.0346(19) 0.045(2) 0.048(2) -0.0043(19) -0.0046(17) 0.0024(18) C8 0.044(2) 0.047(2) 0.041(2) -0.0039(19) 0.0016(18) -0.0033(19) C9 0.0358(19) 0.047(2) 0.049(2) -0.0127(19) 0.0093(18) 0.0004(18) N10 0.056(3) 0.073(3) 0.090(3) -0.048(3) -0.009(2) -0.001(2) C11 0.043(2) 0.057(3) 0.067(3) -0.016(2) -0.008(2) 0.006(2) C12 0.042(2) 0.045(2) 0.045(2) -0.0063(18) 0.0080(19) -0.0074(19) C13 0.038(2) 0.049(2) 0.051(2) -0.008(2) 0.0061(18) -0.0036(19) N14 0.049(2) 0.093(4) 0.086(3) -0.016(3) 0.007(2) -0.006(2) C15 0.051(3) 0.055(3) 0.070(3) -0.021(2) -0.003(2) -0.010(2) C16 0.053(3) 0.048(3) 0.051(3) -0.020(2) -0.004(2) -0.001(2) C17 0.046(2) 0.053(3) 0.044(2) -0.011(2) -0.0071(19) 0.006(2) C18 0.042(2) 0.076(4) 0.077(3) -0.010(3) -0.008(2) 0.017(3) C19 0.056(3) 0.057(3) 0.049(3) -0.014(2) 0.005(2) -0.013(2) C20 0.048(2) 0.057(3) 0.047(2) -0.013(2) -0.008(2) 0.001(2) C21 0.041(2) 0.059(3) 0.068(3) 0.007(2) 0.001(2) -0.001(2) N22 0.086(4) 0.084(4) 0.118(4) -0.052(3) -0.004(3) 0.000(3) C23 0.047(3) 0.067(3) 0.086(4) -0.038(3) -0.014(3) -0.004(2) C24 0.093(4) 0.076(4) 0.086(4) -0.013(3) 0.011(4) 0.010(4) C25 0.069(3) 0.056(3) 0.072(4) -0.020(3) -0.003(3) 0.008(3) C26 0.151(7) 0.070(4) 0.083(4) 0.014(3) 0.021(5) 0.019(4) C27 0.129(5) 0.065(4) 0.066(4) 0.003(3) 0.030(4) 0.015(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' 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 C9 C2 C13 120.5(4) yes C9 C2 C20 119.5(4) yes C13 C2 C20 120.0(4) yes C5 C3 C7 113.1(3) yes C5 C3 H32 109.4 no C7 C3 H32 109.0 no C5 C3 H31 109.2 no C7 C3 H31 108.6 no H32 C3 H31 107.5 no C6 C4 C8 124.8(4) yes C6 C4 C11 115.8(4) yes C8 C4 C11 119.4(4) yes C3 C5 C9 117.9(4) yes C3 C5 C12 119.1(4) yes C9 C5 C12 122.9(4) yes C4 C6 C17 122.2(4) yes C4 C6 H61 120.4 no C17 C6 H61 117.4 no C3 C7 C18 108.7(4) yes C3 C7 C20 108.7(3) yes C18 C7 C20 109.8(4) yes C3 C7 C21 110.6(3) yes C18 C7 C21 109.1(4) yes C20 C7 C21 110.0(4) yes C4 C8 C13 128.7(4) yes C4 C8 H81 117.1 no C13 C8 H81 114.2 no C5 C9 C2 123.8(4) yes C5 C9 H91 117.0 no C2 C9 H91 119.2 no C16 N10 C25 122.4(4) yes C16 N10 C27 119.7(4) yes C25 N10 C27 116.5(4) yes C4 C11 C23 123.0(4) yes C4 C11 H111 118.3 no C23 C11 H111 118.7 no C5 C12 C15 122.2(4) yes C5 C12 C19 122.2(4) yes C15 C12 C19 115.6(4) yes C2 C13 C8 126.1(4) yes C2 C13 H131 117.6 no C8 C13 H131 116.3 no C12 C15 N22 179.4(6) yes N10 C16 C17 121.6(4) yes N10 C16 C23 121.9(4) yes C17 C16 C23 116.5(4) yes C16 C17 C6 121.6(4) yes C16 C17 H171 119.6 no C6 C17 H171 118.8 no C7 C18 H181 108.1 no C7 C18 H182 108.1 no H181 C18 H182 109.1 no C7 C18 H183 110.6 no H181 C18 H183 111.2 no H182 C18 H183 109.7 no C12 C19 N14 178.0(5) yes C7 C20 C2 113.3(3) yes C7 C20 H201 107.3 no C2 C20 H201 108.5 no C7 C20 H202 109.6 no C2 C20 H202 108.3 no H201 C20 H202 109.8 no C7 C21 H212 107.0 no C7 C21 H211 109.1 no H212 C21 H211 111.0 no C7 C21 H213 109.5 no H212 C21 H213 108.9 no H211 C21 H213 111.2 no C16 C23 C11 120.9(4) yes C16 C23 H231 120.0 no C11 C23 H231 119.1 no C25 C24 H241 108.6 no C25 C24 H243 108.7 no H241 C24 H243 106.9 no C25 C24 H242 111.8 no H241 C24 H242 111.5 no H243 C24 H242 109.1 no C24 C25 N10 113.2(5) yes C24 C25 H251 106.5 no N10 C25 H251 108.3 no C24 C25 H252 110.0 no N10 C25 H252 110.1 no H251 C25 H252 108.5 no Cl1 C26 C27 103.1(5) yes Cl1 C26 H261 110.8 no C27 C26 H261 110.5 no Cl1 C26 H262 111.6 no C27 C26 H262 110.9 no H261 C26 H262 109.9 no N10 C27 C26 100.7(5) yes N10 C27 H272 111.9 no C26 C27 H272 111.0 no N10 C27 H271 114.2 no C26 C27 H271 111.2 no H272 C27 H271 107.9 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C26 1.882(8) yes C2 C9 1.348(5) yes C2 C13 1.435(5) yes C2 C20 1.502(6) yes C3 C5 1.503(5) yes C3 C7 1.528(5) yes C3 H32 1.006 no C3 H31 1.010 no C4 C6 1.392(5) yes C4 C8 1.441(5) yes C4 C11 1.390(6) yes C5 C9 1.426(5) yes C5 C12 1.368(5) yes C6 C17 1.374(5) yes C6 H61 0.947 no C7 C18 1.529(5) yes C7 C20 1.522(5) yes C7 C21 1.529(6) yes C8 C13 1.346(5) yes C8 H81 0.938 no C9 H91 0.970 no N10 C16 1.381(5) yes N10 C25 1.468(6) yes N10 C27 1.578(7) yes C11 C23 1.367(6) yes C11 H111 0.936 no C12 C15 1.414(6) yes C12 C19 1.431(6) yes C13 H131 0.939 no N14 C19 1.131(6) yes C15 N22 1.133(6) yes C16 C17 1.394(5) yes C16 C23 1.405(6) yes C17 H171 0.935 no C18 H181 0.946 no C18 H182 0.968 no C18 H183 0.973 no C20 H201 0.997 no C20 H202 1.002 no C21 H212 0.951 no C21 H211 0.964 no C21 H213 0.958 no C23 H231 0.918 no C24 C25 1.507(7) yes C24 H241 0.969 no C24 H243 0.976 no C24 H242 0.974 no C25 H251 0.989 no C25 H252 0.989 no C26 C27 1.401(8) yes C26 H261 0.977 no C26 H262 0.969 no C27 H272 0.996 no C27 H271 0.987 no _journal_paper_doi 10.1021/cm102165r