#------------------------------------------------------------------------------ #$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $ #$Revision: 176453 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/10/18/7101845.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_7101845 loop_ _publ_author_name 'Ashley, Andrew E' 'Cowley, Andrew R' 'O'Hare, Dermot' _publ_section_title ; The hexamethylpentalene dianion and other reagents for organometallic pentalene chemistry. ; _journal_issue 15 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 1512 _journal_page_last 1514 _journal_paper_doi 10.1039/b702150j _journal_year 2007 _chemical_compound_source ; synthesis as described ; _chemical_formula_moiety ' C26 H50 Li2 N4 ' _chemical_formula_sum 'C26 H50 Li2 N4' _chemical_formula_weight 432.58 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _cell_angle_alpha 90 _cell_angle_beta 90.8093(7) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.8575(2) _cell_length_b 9.3133(2) _cell_length_c 14.1063(3) _cell_measurement_reflns_used 14757 _cell_measurement_temperature 150 _cell_measurement_theta_max 28 _cell_measurement_theta_min 5 _cell_volume 1426.27(5) _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 14757 _diffrn_reflns_theta_full 27.475 _diffrn_reflns_theta_max 27.475 _diffrn_reflns_theta_min 5.186 _diffrn_standards_decay_% 0.00 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.058 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_crystal_colour ' orange ' _exptl_crystal_density_diffrn 1.007 _exptl_crystal_description ' prism ' _exptl_crystal_F_000 480 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_thermal_history ; The material was crystallised at ambient temperature. A suitable crystal was cooled rapidly to 150K for single-crystal X-ray diffraction analysis. ; _refine_diff_density_max 0.63 _refine_diff_density_min -0.35 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0173 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2297 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0934 _refine_ls_R_factor_gt 0.0709 _refine_ls_shift/su_max 0.017615 _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: 1.85 1.58 1.10 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1117 _refine_ls_wR_factor_gt 0.0961 _refine_ls_wR_factor_ref 0.0961 _reflns_limit_h_max 14 _reflns_limit_h_min -14 _reflns_limit_k_max 12 _reflns_limit_k_min 0 _reflns_limit_l_max 18 _reflns_limit_l_min 0 _reflns_number_gt 2297 _reflns_number_total 3232 _reflns_threshold_expression I>3.00u(I) _cod_data_source_file b702150j.txt _cod_data_source_block arc1441 _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_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_original_sg_symbol_H-M 'P 1 21/n 1 ' _cod_original_formula_sum ' C26 H50 Li2 N4 ' _cod_database_code 7101845 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-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 Li1 Li 0.6378(3) 0.3415(3) 0.4736(2) 0.0319 1.0000 Uani . C1 C 0.55369(18) 0.4159(2) 0.60785(12) 0.0332 1.0000 Uani D C2 C 0.66283(17) 0.4958(2) 0.59147(14) 0.0359 1.0000 Uani D C3 C 0.65313(16) 0.57397(19) 0.50548(14) 0.0324 1.0000 Uani D C4 C 0.53071(15) 0.54889(17) 0.46832(12) 0.0265 1.0000 Uani . C5 C 0.5270(3) 0.3246(3) 0.69310(16) 0.0521 1.0000 Uani D C6 C 0.7717(2) 0.5054(3) 0.65888(19) 0.0587 1.0000 Uani D C7 C 0.7487(2) 0.6734(3) 0.4665(2) 0.0519 1.0000 Uani D N1 N 0.79323(15) 0.19223(19) 0.48149(13) 0.0422 1.0000 Uani . C8 C 0.7645(2) 0.0775(3) 0.4135(2) 0.0613 1.0000 Uani . C9 C 0.6999(2) 0.1280(3) 0.32726(19) 0.0574 1.0000 Uani . N2 N 0.59175(15) 0.21698(18) 0.34904(12) 0.0388 1.0000 Uani . C10 C 0.9004(2) 0.2734(4) 0.4538(3) 0.0698 1.0000 Uani . C11 C 0.8119(3) 0.1264(3) 0.5745(2) 0.0662 1.0000 Uani . C12 C 0.4838(3) 0.1358(3) 0.37551(18) 0.0573 1.0000 Uani . C13 C 0.5605(3) 0.3002(3) 0.26447(17) 0.0569 1.0000 Uani . H51 H 0.474(3) 0.378(3) 0.741(2) 0.087(10) 1.0000 Uiso D H52 H 0.602(3) 0.288(4) 0.722(2) 0.101(12) 1.0000 Uiso D H53 H 0.481(3) 0.242(3) 0.678(2) 0.076(10) 1.0000 Uiso D H61 H 0.768(3) 0.592(4) 0.699(3) 0.112(14) 1.0000 Uiso D H62 H 0.853(3) 0.503(3) 0.6259(19) 0.063(8) 1.0000 Uiso D H63 H 0.768(3) 0.426(4) 0.705(3) 0.106(14) 1.0000 Uiso D H71 H 0.761(3) 0.756(4) 0.509(2) 0.087(11) 1.0000 Uiso D H72 H 0.718(3) 0.716(4) 0.403(2) 0.099(12) 1.0000 Uiso D H73 H 0.830(3) 0.627(4) 0.459(3) 0.131(16) 1.0000 Uiso D H81 H 0.8434 0.0311 0.3945 0.0734 1.0000 Uiso . H82 H 0.7112 0.0051 0.4455 0.0734 1.0000 Uiso . H91 H 0.7584 0.1862 0.2889 0.0688 1.0000 Uiso . H92 H 0.6721 0.0427 0.2896 0.0688 1.0000 Uiso . H101 H 0.9173 0.3504 0.5017 0.0840 1.0000 Uiso . H102 H 0.9732 0.2078 0.4505 0.0840 1.0000 Uiso . H103 H 0.8850 0.3179 0.3903 0.0840 1.0000 Uiso . H111 H 0.8317 0.2026 0.6223 0.0793 1.0000 Uiso . H112 H 0.8817 0.0565 0.5717 0.0793 1.0000 Uiso . H113 H 0.7352 0.0750 0.5933 0.0793 1.0000 Uiso . H121 H 0.4147 0.2034 0.3891 0.0688 1.0000 Uiso . H122 H 0.5030 0.0776 0.4334 0.0688 1.0000 Uiso . H123 H 0.4591 0.0705 0.3223 0.0688 1.0000 Uiso . H131 H 0.4872 0.3618 0.2773 0.0683 1.0000 Uiso . H132 H 0.6319 0.3624 0.2474 0.0683 1.0000 Uiso . H133 H 0.5411 0.2334 0.2108 0.0683 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 Li1 0.0315(14) 0.0324(15) 0.0319(14) -0.0032(12) 0.0003(11) 0.0015(12) C1 0.0385(9) 0.0351(9) 0.0261(8) -0.0004(7) 0.0007(7) 0.0095(7) C2 0.0310(9) 0.0404(10) 0.0361(9) -0.0104(8) -0.0068(7) 0.0068(7) C3 0.0267(8) 0.0303(9) 0.0403(9) -0.0056(7) 0.0020(7) -0.0009(6) C4 0.0254(8) 0.0264(8) 0.0276(7) 0.0000(7) 0.0026(6) 0.0029(6) C5 0.0671(15) 0.0548(14) 0.0347(10) 0.0146(10) 0.0094(10) 0.0188(12) C6 0.0458(13) 0.0760(18) 0.0536(13) -0.0276(13) -0.0222(11) 0.0175(12) C7 0.0384(11) 0.0428(12) 0.0750(16) -0.0066(11) 0.0143(11) -0.0115(9) N1 0.0366(9) 0.0466(10) 0.0432(9) -0.0096(7) -0.0061(7) 0.0109(7) C8 0.0602(14) 0.0575(14) 0.0657(15) -0.0243(12) -0.0177(12) 0.0272(12) C9 0.0529(13) 0.0613(15) 0.0577(13) -0.0218(12) -0.0080(11) 0.0179(11) N2 0.0362(8) 0.0394(9) 0.0406(9) -0.0112(7) -0.0056(7) 0.0066(6) C10 0.0441(13) 0.0727(18) 0.093(2) -0.0188(16) 0.0138(13) 0.0012(12) C11 0.0776(17) 0.0639(16) 0.0567(14) 0.0013(13) -0.0100(13) 0.0248(14) C12 0.0681(15) 0.0504(13) 0.0536(13) -0.0055(11) 0.0051(11) -0.0133(12) C13 0.0700(16) 0.0602(15) 0.0405(12) -0.0037(11) 0.0048(10) 0.0049(12) 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_IV_Table_2.2B '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_IV_Table_2.2B 'Li ' -0.0003 0.0001 1.1282 3.9546 0.7508 1.0524 0.6175 85.3905 0.4653 168.2610 0.0377 International_Tables_Vol_IV_Table_2.2B '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_IV_Table_2.2B loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . Li1 C2 . 37.38(9) yes C1 . Li1 C3 . 63.52(11) yes C2 . Li1 C3 . 37.34(9) yes C1 . Li1 C4 . 62.88(10) yes C2 . Li1 C4 . 61.72(10) yes C3 . Li1 C4 . 37.59(8) yes C1 . Li1 C4 2_666 37.47(8) yes C2 . Li1 C4 2_666 61.67(10) yes C3 . Li1 C4 2_666 62.89(10) yes C4 . Li1 C4 2_666 37.36(9) yes C1 . Li1 N1 . 118.69(15) yes C2 . Li1 N1 . 106.74(14) yes C3 . Li1 N1 . 123.66(15) yes C4 . Li1 N1 . 160.51(17) yes C4 2_666 Li1 N1 . 153.73(16) yes C1 . Li1 N2 . 140.12(16) yes C2 . Li1 N2 . 170.39(17) yes C3 . Li1 N2 . 134.89(16) yes C4 . Li1 N2 . 108.67(14) yes C4 2_666 Li1 N2 . 111.03(14) yes N1 . Li1 N2 . 82.49(12) yes Li1 . C1 C2 . 70.82(13) yes Li1 . C1 C4 2_666 72.56(12) yes C2 . C1 C4 2_666 106.41(16) yes Li1 . C1 C5 . 126.24(16) yes C2 . C1 C5 . 126.63(18) yes C4 2_666 C1 C5 . 126.68(19) yes Li1 . C2 C1 . 71.80(13) yes Li1 . C2 C3 . 71.54(13) yes C1 . C2 C3 . 110.87(16) yes Li1 . C2 C6 . 126.83(16) yes C1 . C2 C6 . 125.2(2) yes C3 . C2 C6 . 123.8(2) yes Li1 . C3 C2 . 71.12(13) yes Li1 . C3 C4 . 72.64(12) yes C2 . C3 C4 . 106.56(15) yes Li1 . C3 C7 . 125.35(16) yes C2 . C3 C7 . 125.96(19) yes C4 . C3 C7 . 127.27(19) yes Li1 . C4 Li1 2_666 142.64(9) yes Li1 . C4 C1 2_666 122.84(14) yes Li1 2_666 C4 C1 2_666 69.97(12) yes Li1 . C4 C3 . 69.78(12) yes Li1 2_666 C4 C3 . 122.85(14) yes C1 2_666 C4 C3 . 143.94(17) yes Li1 . C4 C4 2_666 71.46(14) yes Li1 2_666 C4 C4 2_666 71.18(14) yes C1 2_666 C4 C4 2_666 108.10(18) yes C3 . C4 C4 2_666 107.96(18) yes C1 . C5 H51 . 112.0(17) no C1 . C5 H52 . 111.6(19) no H51 . C5 H52 . 111(2) no C1 . C5 H53 . 113.0(18) no H51 . C5 H53 . 104(2) no H52 . C5 H53 . 105(2) no C2 . C6 H61 . 112(2) no C2 . C6 H62 . 113.1(16) no H61 . C6 H62 . 109(2) no C2 . C6 H63 . 109(2) no H61 . C6 H63 . 103(2) no H62 . C6 H63 . 109(2) no C3 . C7 H71 . 110.4(18) no C3 . C7 H72 . 109.9(19) no H71 . C7 H72 . 105(2) no C3 . C7 H73 . 113(2) no H71 . C7 H73 . 107(3) no H72 . C7 H73 . 110(3) no Li1 . N1 C8 . 105.85(15) yes Li1 . N1 C10 . 106.12(17) yes C8 . N1 C10 . 111.7(2) yes Li1 . N1 C11 . 114.19(17) yes C8 . N1 C11 . 107.9(2) yes C10 . N1 C11 . 111.1(2) yes N1 . C8 C9 . 113.7(2) yes N1 . C8 H81 . 108.406 no C9 . C8 H81 . 108.406 no N1 . C8 H82 . 108.405 no C9 . C8 H82 . 108.405 no H81 . C8 H82 . 109.466 no C8 . C9 N2 . 112.3(2) yes C8 . C9 H91 . 108.770 no N2 . C9 H91 . 108.770 no C8 . C9 H92 . 108.772 no N2 . C9 H92 . 108.771 no H91 . C9 H92 . 109.466 no Li1 . N2 C9 . 107.22(15) yes Li1 . N2 C12 . 104.44(15) yes C9 . N2 C12 . 114.3(2) yes Li1 . N2 C13 . 115.40(16) yes C9 . N2 C13 . 107.76(19) yes C12 . N2 C13 . 107.98(18) yes N1 . C10 H101 . 109.466 no N1 . C10 H102 . 109.467 no H101 . C10 H102 . 109.475 no N1 . C10 H103 . 109.467 no H101 . C10 H103 . 109.475 no H102 . C10 H103 . 109.477 no N1 . C11 H111 . 109.467 no N1 . C11 H112 . 109.466 no H111 . C11 H112 . 109.476 no N1 . C11 H113 . 109.467 no H111 . C11 H113 . 109.476 no H112 . C11 H113 . 109.476 no N2 . C12 H121 . 109.467 no N2 . C12 H122 . 109.466 no H121 . C12 H122 . 109.475 no N2 . C12 H123 . 109.467 no H121 . C12 H123 . 109.476 no H122 . C12 H123 . 109.476 no N2 . C13 H131 . 109.467 no N2 . C13 H132 . 109.467 no H131 . C13 H132 . 109.476 no N2 . C13 H133 . 109.467 no H131 . C13 H133 . 109.475 no H132 . C13 H133 . 109.476 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Li1 C1 . 2.224(3) yes Li1 C2 . 2.211(3) yes Li1 C3 . 2.217(4) yes Li1 C4 . 2.255(3) yes Li1 C4 2_666 2.258(3) yes Li1 N1 . 2.189(3) yes Li1 N2 . 2.158(3) yes C1 C2 . 1.421(3) yes C1 C4 2_666 1.440(2) yes C1 C5 . 1.504(3) yes C2 C3 . 1.417(3) yes C2 C6 . 1.509(3) yes C3 C4 . 1.441(2) yes C3 C7 . 1.501(3) yes C4 C4 2_666 1.446(3) yes C5 H51 . 1.02(3) no C5 H52 . 0.97(3) no C5 H53 . 0.94(3) no C6 H61 . 0.99(3) no C6 H62 . 1.00(3) no C6 H63 . 0.99(3) no C7 H71 . 0.98(3) no C7 H72 . 1.03(3) no C7 H73 . 0.99(4) no N1 C8 . 1.466(3) yes N1 C10 . 1.446(3) yes N1 C11 . 1.460(3) yes C8 C9 . 1.473(4) yes C8 H81 . 1.000 no C8 H82 . 1.000 no C9 N2 . 1.474(3) yes C9 H91 . 1.000 no C9 H92 . 1.000 no N2 C12 . 1.448(3) yes N2 C13 . 1.459(3) yes C10 H101 . 1.000 no C10 H102 . 1.000 no C10 H103 . 1.000 no C11 H111 . 1.000 no C11 H112 . 1.000 no C11 H113 . 1.000 no C12 H121 . 1.000 no C12 H122 . 1.000 no C12 H123 . 1.000 no C13 H131 . 1.000 no C13 H132 . 1.000 no C13 H133 . 1.000 no