#------------------------------------------------------------------------------ #$Date: 2016-02-13 12:50:18 +0000 (Sat, 13 Feb 2016) $ #$Revision: 176428 $ #$URL: svn://www.crystallography.net/cod/cif/4/06/05/4060521.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_4060521 loop_ _publ_author_name 'Liddle, Stephen T.' 'Arnold, Polly L.' _publ_section_title ; Synthesis of Heteroleptic Cerium(III) Anionic Amido-Tethered N-Heterocyclic Carbene Complexes ; _journal_issue 11 _journal_name_full Organometallics _journal_page_first 2597 _journal_page_last 2605 _journal_paper_doi 10.1021/om050061b _journal_volume 24 _journal_year 2005 _chemical_absolute_configuration ad _chemical_formula_moiety 'C10 H21 N3, 2(Br)' _chemical_formula_sum 'C10 H21 Br2 N3' _chemical_formula_weight 343.12 _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _cell_angle_alpha 90.00 _cell_angle_beta 94.608(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 5.9163(4) _cell_length_b 11.0261(8) _cell_length_c 11.0801(8) _cell_measurement_reflns_used 5024 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.53 _cell_measurement_theta_min 2.61 _cell_volume 720.46(9) _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2000)' _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_av_sigmaI/netI 0.041 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5078 _diffrn_reflns_theta_full 24.98 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_min 2.61 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count . _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 5.604 _exptl_absorpt_correction_T_max 0.400 _exptl_absorpt_correction_T_min 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.31 _refine_diff_density_min -0.42 _refine_diff_density_rms 0.05 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.027(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.89 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 2486 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.89 _refine_ls_R_factor_all 0.0164 _refine_ls_R_factor_gt 0.0159 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0397 _reflns_number_gt 2430 _reflns_number_total 2486 _reflns_threshold_expression I>2\s(I) _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 21' _cod_database_code 4060521 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 N1 0.0121(10) 0.0103(10) 0.0143(10) 0.0007(8) 0.0000(7) 0.0001(8) N2 0.0200(9) 0.0123(10) 0.0159(9) -0.0036(7) 0.0057(7) 0.0000(8) N3 0.0236(11) 0.0116(10) 0.0192(11) -0.0032(9) 0.0036(8) -0.0005(9) C1 0.0221(13) 0.0111(12) 0.0221(13) -0.0032(10) 0.0080(10) -0.0006(10) C2 0.0252(13) 0.0183(13) 0.0213(13) -0.0047(10) 0.0084(10) -0.0056(10) C3 0.0334(14) 0.0142(13) 0.0212(13) -0.0017(10) 0.0108(11) -0.0049(11) C4 0.0246(13) 0.0250(15) 0.0302(15) -0.0010(12) -0.0062(11) 0.0054(12) C5 0.0293(14) 0.0210(14) 0.0201(13) -0.0017(11) 0.0040(10) 0.0106(11) C6 0.0171(12) 0.0260(14) 0.0188(13) -0.0013(11) 0.0011(10) 0.0051(11) C7 0.0164(11) 0.0116(12) 0.0151(11) -0.0028(9) -0.0006(9) -0.0007(10) C8 0.0240(13) 0.0280(14) 0.0214(14) -0.0051(11) 0.0087(11) 0.0006(11) C9 0.0272(14) 0.0234(15) 0.0156(13) 0.0013(10) -0.0041(10) 0.0002(11) C10 0.0265(13) 0.0148(15) 0.0244(13) -0.0012(11) 0.0013(10) -0.0047(10) Br1 0.0210(1) 0.0131(1) 0.0344(2) 0.0047(1) -0.0013(1) -0.0013(1) Br2 0.0164(1) 0.0170(1) 0.0212(1) 0.0061(1) 0.0018(1) 0.0034(1) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N1 N Uani 0.9715(3) 0.61566(18) 0.26913(18) 1.000 0.0123(6) . . N2 N Uani 1.0089(4) 0.53988(19) -0.0031(2) 1.000 0.0158(5) . . N3 N Uani 0.7859(3) 0.57408(18) -0.16310(17) 1.000 0.0180(6) . . C1 C Uani 0.8121(4) 0.5096(2) -0.0618(2) 1.000 0.0181(7) . . C2 C Uani 1.1106(4) 0.6275(2) -0.0694(2) 1.000 0.0213(8) . . C3 C Uani 0.9708(4) 0.6489(2) -0.1690(2) 1.000 0.0225(8) . . C4 C Uani 0.5889(4) 0.5690(3) -0.2526(2) 1.000 0.0271(8) . . C5 C Uani 1.1061(4) 0.4820(3) 0.1083(2) 1.000 0.0234(8) . . C6 C Uani 1.1714(4) 0.5698(3) 0.2090(2) 1.000 0.0207(8) . . C7 C Uani 1.0251(4) 0.6887(2) 0.38523(19) 1.000 0.0145(7) . . C8 C Uani 0.7964(4) 0.7216(2) 0.4318(2) 1.000 0.0241(8) . . C9 C Uani 1.1601(4) 0.6079(2) 0.4776(2) 1.000 0.0224(8) . . C10 C Uani 1.1549(4) 0.8015(2) 0.3546(2) 1.000 0.0219(8) . . Br1 Br Uani 0.66099(4) 0.37932(2) 0.30984(2) 1.000 0.0230(1) . . Br2 Br Uani 0.62468(3) 0.77901(2) 0.08985(2) 1.000 0.0182(1) . . H1A H Uiso 0.70780 0.45160 -0.03560 1.000 0.0220 calc R H1N H Uiso 0.882(4) 0.555(3) 0.284(2) 1.000 0.0150 . . H2A H Uiso 1.25240 0.66560 -0.04870 1.000 0.0260 calc R H2N H Uiso 0.881(4) 0.661(2) 0.213(2) 1.000 0.0150 . . H3A H Uiso 0.99530 0.70500 -0.23170 1.000 0.0270 calc R H4A H Uiso 0.48460 0.50560 -0.22950 1.000 0.0410 calc R H4B H Uiso 0.63990 0.55040 -0.33250 1.000 0.0410 calc R H4C H Uiso 0.51100 0.64750 -0.25540 1.000 0.0410 calc R H5A H Uiso 1.24220 0.43550 0.08980 1.000 0.0280 calc R H5B H Uiso 0.99440 0.42370 0.13650 1.000 0.0280 calc R H6A H Uiso 1.27690 0.52920 0.27010 1.000 0.0250 calc R H6B H Uiso 1.25230 0.63940 0.17590 1.000 0.0250 calc R H8A H Uiso 0.82150 0.76400 0.50940 1.000 0.0360 calc R H8B H Uiso 0.70910 0.64740 0.44280 1.000 0.0360 calc R H8C H Uiso 0.71210 0.77440 0.37300 1.000 0.0360 calc R H9A H Uiso 1.18270 0.65070 0.55520 1.000 0.0340 calc R H9B H Uiso 1.30790 0.58880 0.44810 1.000 0.0340 calc R H9C H Uiso 1.07630 0.53260 0.48850 1.000 0.0340 calc R H10A H Uiso 1.18730 0.85020 0.42800 1.000 0.0330 calc R H10B H Uiso 1.06370 0.84930 0.29410 1.000 0.0330 calc R H10C H Uiso 1.29770 0.77810 0.32200 1.000 0.0330 calc R loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 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_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C7 115.85(18) . . . yes C1 N2 C2 108.5(2) . . . yes C1 N2 C5 124.9(2) . . . yes C2 N2 C5 126.5(2) . . . yes C1 N3 C3 108.79(19) . . . yes C1 N3 C4 125.6(2) . . . yes C3 N3 C4 125.6(2) . . . yes H1N N1 H2N 102(2) . . . no C6 N1 H1N 109.7(19) . . . no C6 N1 H2N 108.5(14) . . . no C7 N1 H1N 109.3(15) . . . no C7 N1 H2N 110.4(14) . . . no N2 C1 N3 108.5(2) . . . yes N2 C2 C3 107.1(2) . . . yes N3 C3 C2 107.1(2) . . . yes N2 C5 C6 113.9(3) . . . yes N1 C6 C5 112.58(19) . . . yes C8 C7 C10 111.04(18) . . . no C9 C7 C10 112.38(19) . . . no N1 C7 C8 106.22(18) . . . yes N1 C7 C9 108.51(17) . . . yes N1 C7 C10 108.58(17) . . . yes C8 C7 C9 109.89(18) . . . no N2 C1 H1A 126.00 . . . no N3 C1 H1A 126.00 . . . no N2 C2 H2A 127.00 . . . no C3 C2 H2A 126.00 . . . no N3 C3 H3A 126.00 . . . no C2 C3 H3A 126.00 . . . no N3 C4 H4A 109.00 . . . no N3 C4 H4B 109.00 . . . no N3 C4 H4C 109.00 . . . no H4A C4 H4B 109.00 . . . no H4A C4 H4C 110.00 . . . no H4B C4 H4C 110.00 . . . no N2 C5 H5A 109.00 . . . no N2 C5 H5B 109.00 . . . no C6 C5 H5A 109.00 . . . no C6 C5 H5B 109.00 . . . no H5A C5 H5B 108.00 . . . no N1 C6 H6A 109.00 . . . no N1 C6 H6B 109.00 . . . no C5 C6 H6A 109.00 . . . no C5 C6 H6B 109.00 . . . no H6A C6 H6B 108.00 . . . no C7 C8 H8A 109.00 . . . no C7 C8 H8B 109.00 . . . no C7 C8 H8C 109.00 . . . no H8A C8 H8B 109.00 . . . no H8A C8 H8C 109.00 . . . no H8B C8 H8C 109.00 . . . no C7 C9 H9A 109.00 . . . no C7 C9 H9B 109.00 . . . no C7 C9 H9C 109.00 . . . no H9A C9 H9B 109.00 . . . no H9A C9 H9C 110.00 . . . no H9B C9 H9C 109.00 . . . no C7 C10 H10A 109.00 . . . no C7 C10 H10B 109.00 . . . no C7 C10 H10C 110.00 . . . no H10A C10 H10B 109.00 . . . no H10A C10 H10C 109.00 . . . no H10B C10 H10C 109.00 . . . no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.492(3) . . yes N1 C7 1.529(3) . . yes N2 C1 1.330(3) . . yes N2 C2 1.381(3) . . yes N2 C5 1.465(3) . . yes N3 C1 1.327(3) . . yes N3 C3 1.376(3) . . yes N3 C4 1.469(3) . . yes N1 H2N 0.93(2) . . no N1 H1N 0.88(3) . . no C2 C3 1.346(3) . . no C5 C6 1.504(4) . . no C7 C10 1.515(3) . . no C7 C8 1.530(3) . . no C7 C9 1.532(3) . . no C1 H1A 0.9500 . . no C2 H2A 0.9500 . . no C3 H3A 0.9500 . . no C4 H4A 0.9800 . . no C4 H4B 0.9800 . . no C4 H4C 0.9800 . . no C5 H5A 0.9900 . . no C5 H5B 0.9900 . . no C6 H6A 0.9900 . . no C6 H6B 0.9900 . . no C8 H8A 0.9800 . . no C8 H8B 0.9800 . . no C8 H8C 0.9800 . . no C9 H9A 0.9800 . . no C9 H9B 0.9800 . . no C9 H9C 0.9800 . . no C10 H10A 0.9800 . . no C10 H10B 0.9800 . . no C10 H10C 0.9800 . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1N Br1 0.88(3) 2.37(3) 3.2407(19) 174(2) . yes N1 H2N Br2 0.93(2) 2.35(2) 3.2780(19) 173(2) . yes C1 H1A Br2 0.9500 2.7700 3.621(2) 150.00 2_645 yes C2 H2A Br2 0.9500 2.8700 3.781(2) 161.00 1_655 yes C4 H4C Br1 0.9800 2.8000 3.761(3) 167.00 2_655 yes C5 H5A Br2 0.9900 2.7900 3.596(3) 138.00 2_745 yes C5 H5B Br1 0.9900 2.9000 3.761(2) 146.00 . yes C6 H6A Br1 0.9900 2.8200 3.678(3) 146.00 1_655 yes C6 H6B Br2 0.9900 2.9100 3.850(3) 159.00 1_655 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C6 C5 170.3(2) . . . . no C6 N1 C7 C8 -178.1(2) . . . . no C6 N1 C7 C9 -60.0(3) . . . . no C6 N1 C7 C10 62.4(3) . . . . no C2 N2 C1 N3 0.4(3) . . . . no C5 N2 C1 N3 -175.3(2) . . . . no C1 N2 C2 C3 -0.1(3) . . . . no C5 N2 C2 C3 175.5(2) . . . . no C1 N2 C5 C6 -127.4(3) . . . . no C2 N2 C5 C6 57.7(3) . . . . no C3 N3 C1 N2 -0.6(3) . . . . no C4 N3 C1 N2 -179.0(2) . . . . no C1 N3 C3 C2 0.5(3) . . . . no C4 N3 C3 C2 178.9(2) . . . . no N2 C2 C3 N3 -0.3(3) . . . . no N2 C5 C6 N1 76.4(3) . . . . no