#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/44/2204436.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2204436
loop_
_publ_author_name
'Clegg, William'
'Liddle, Stephen T.'
_publ_section_title
;
 Bis[μ-2-(phenylamido)pyridine]bis{[2-(phenylamino)pyridine]lithium(I)}
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1587
_journal_page_last               m1589
_journal_paper_doi               10.1107/S1600536804024766
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '[Li2 (C11 H9 N2)2 (C11 H10 N2)2]'
_chemical_formula_moiety         'C44 H38 Li2 N8'
_chemical_formula_sum            'C44 H38 Li2 N8'
_chemical_formula_weight         692.70
_chemical_name_systematic
;
Bis[μ-2-(phenylamido)pyridine]bis{[2-(phenylamino)pyridine]lithium(I)}
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                116.715(2)
_cell_angle_beta                 92.739(2)
_cell_angle_gamma                91.216(2)
_cell_formula_units_Z            1
_cell_length_a                   8.7031(8)
_cell_length_b                   10.3718(10)
_cell_length_c                   11.5289(11)
_cell_measurement_reflns_used    3543
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.54
_cell_measurement_theta_min      2.20
_cell_volume                     927.46(15)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2001)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type  'Bruker SMART 1K CCD'
_diffrn_measurement_method       'thin-slice ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5683
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.59
_diffrn_reflns_theta_min         1.98
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.198
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0563P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                2868
_reflns_number_total             4165
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6534.cif
_cod_data_source_block           I
_cod_database_code               2204436
_cod_database_fobs_code          2204436
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
Li 0.3855(3) 0.5671(3) 0.5221(2) 0.0406(6) Uani d 1 Li
N1 0.27806(13) 0.42171(12) 0.56848(11) 0.0317(3) Uani d 1 N
N2 0.52228(12) 0.50692(11) 0.65280(10) 0.0264(2) Uani d 1 N
C1 0.14004(17) 0.36108(15) 0.56935(15) 0.0357(3) Uani d 1 C
H1 0.0743(18) 0.3379(16) 0.4933(15) 0.044(4) Uiso d 1 H
C2 0.09729(17) 0.33301(16) 0.66845(15) 0.0372(3) Uani d 1 C
H2 -0.0035(19) 0.2903(16) 0.6635(15) 0.045(4) Uiso d 1 H
C3 0.20271(18) 0.36851(16) 0.77320(15) 0.0395(4) Uani d 1 C
H3 0.1773(19) 0.3497(17) 0.8474(16) 0.056(5) Uiso d 1 H
C4 0.34521(17) 0.42868(15) 0.77534(14) 0.0338(3) Uani d 1 C
H4 0.4166(18) 0.4513(16) 0.8458(14) 0.040(4) Uiso d 1 H
C5 0.38331(15) 0.45526(13) 0.67015(12) 0.0253(3) Uani d 1 C
C6 0.62527(15) 0.58820(13) 0.76016(12) 0.0251(3) Uani d 1 C
C7 0.58101(17) 0.68904(15) 0.88262(13) 0.0327(3) Uani d 1 C
H7 0.4730(19) 0.7012(16) 0.8940(14) 0.043(4) Uiso d 1 H
C8 0.68913(18) 0.76838(16) 0.98206(14) 0.0386(4) Uani d 1 C
H8 0.6545(18) 0.8382(17) 1.0639(15) 0.048(4) Uiso d 1 H
C9 0.84486(18) 0.75217(16) 0.96387(14) 0.0381(4) Uani d 1 C
H9 0.9204(17) 0.8091(15) 1.0341(14) 0.038(4) Uiso d 1 H
C10 0.89026(17) 0.65500(15) 0.84356(14) 0.0355(3) Uani d 1 C
H10 1.0009(19) 0.6393(16) 0.8305(15) 0.047(4) Uiso d 1 H
C11 0.78262(16) 0.57577(14) 0.74348(13) 0.0293(3) Uani d 1 C
H11 0.8158(19) 0.5099(17) 0.6655(16) 0.051(5) Uiso d 1 H
N3 0.28231(13) 0.75574(11) 0.59060(11) 0.0314(3) Uani d 1 N
N4 0.33760(14) 0.79794(13) 0.41807(11) 0.0323(3) Uani d 1 N
H4N 0.3784(19) 0.7106(17) 0.3870(15) 0.046(4) Uiso d 1 H
C12 0.20863(18) 0.78881(16) 0.69984(14) 0.0370(3) Uani d 1 C
H12 0.2276(17) 0.7254(16) 0.7419(14) 0.042(4) Uiso d 1 H
C13 0.11184(19) 0.90076(15) 0.75203(14) 0.0385(4) Uani d 1 C
H13 0.065(2) 0.9179(17) 0.8293(16) 0.051(5) Uiso d 1 H
C14 0.09143(18) 0.98592(15) 0.68881(14) 0.0370(3) Uani d 1 C
H14 0.0199(19) 1.0660(17) 0.7219(15) 0.047(4) Uiso d 1 H
C15 0.16715(16) 0.95821(14) 0.57888(14) 0.0333(3) Uani d 1 C
H15 0.1526(17) 1.0182(16) 0.5340(14) 0.041(4) Uiso d 1 H
C16 0.26182(15) 0.84025(13) 0.53066(12) 0.0278(3) Uani d 1 C
C17 0.31804(15) 0.85230(14) 0.32528(13) 0.0306(3) Uani d 1 C
C18 0.34383(18) 0.99792(17) 0.35960(17) 0.0407(4) Uani d 1 C
H18 0.3774(18) 1.0631(17) 0.4482(15) 0.044(4) Uiso d 1 H
C19 0.3265(2) 1.0454(2) 0.2653(2) 0.0527(5) Uani d 1 C
H19 0.347(2) 1.144(2) 0.2929(18) 0.074(6) Uiso d 1 H
C20 0.2847(2) 0.9495(2) 0.13783(19) 0.0540(5) Uani d 1 C
H20 0.271(2) 0.9811(19) 0.0716(18) 0.066(5) Uiso d 1 H
C21 0.26074(18) 0.8049(2) 0.10362(17) 0.0455(4) Uani d 1 C
H21 0.229(2) 0.7353(18) 0.0125(17) 0.056(5) Uiso d 1 H
C22 0.27653(16) 0.75598(17) 0.19709(14) 0.0354(3) Uani d 1 C
H22 0.2593(18) 0.6514(17) 0.1689(15) 0.047(4) Uiso d 1 H
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'
Li Li -0.0003 0.0001 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Li N2 . . 65.19(8) yes
N1 Li N2 . 2_666 118.30(13) yes
N1 Li N3 . . 112.43(13) yes
N2 Li N2 . 2_666 110.67(12) yes
N2 Li N3 . . 120.85(13) yes
N2 Li N3 2_666 . 118.54(12) yes
Li N1 C1 . . 143.87(12) ?
Li N1 C5 . . 90.45(11) ?
C1 N1 C5 . . 119.05(12) ?
Li N2 Li . 2_666 69.33(12) ?
Li N2 C5 . . 84.03(10) ?
Li N2 C5 2_666 . 123.09(12) ?
Li N2 C6 . . 131.59(11) ?
Li N2 C6 2_666 . 114.85(11) ?
C5 N2 C6 . . 120.29(10) ?
N1 C1 H1 . . 113.8(9) ?
N1 C1 C2 . . 123.67(14) ?
H1 C1 C2 . . 122.5(9) ?
C1 C2 H2 . . 119.6(9) ?
C1 C2 C3 . . 117.76(14) ?
H2 C2 C3 . . 122.7(9) ?
C2 C3 H3 . . 120.8(9) ?
C2 C3 C4 . . 120.40(14) ?
H3 C3 C4 . . 118.8(10) ?
C3 C4 H4 . . 120.1(9) ?
C3 C4 C5 . . 119.42(13) ?
H4 C4 C5 . . 120.5(9) ?
N1 C5 N2 . . 113.04(11) ?
N1 C5 C4 . . 119.68(12) ?
N2 C5 C4 . . 127.20(12) ?
N2 C6 C7 . . 124.44(12) ?
N2 C6 C11 . . 118.43(11) ?
C7 C6 C11 . . 117.00(12) ?
C6 C7 H7 . . 117.7(9) ?
C6 C7 C8 . . 121.09(14) ?
H7 C7 C8 . . 121.2(9) ?
C7 C8 H8 . . 118.7(10) ?
C7 C8 C9 . . 120.83(14) ?
H8 C8 C9 . . 120.4(10) ?
C8 C9 H9 . . 120.4(9) ?
C8 C9 C10 . . 118.78(14) ?
H9 C9 C10 . . 120.8(9) ?
C9 C10 H10 . . 119.5(9) ?
C9 C10 C11 . . 120.66(14) ?
H10 C10 C11 . . 119.8(9) ?
C6 C11 C10 . . 121.60(13) ?
C6 C11 H11 . . 119.4(10) ?
C10 C11 H11 . . 118.9(10) ?
Li N3 C12 . . 114.62(11) ?
Li N3 C16 . . 127.06(11) ?
C12 N3 C16 . . 117.65(12) ?
H4N N4 C16 . . 116.2(10) ?
H4N N4 C17 . . 114.3(10) ?
C16 N4 C17 . . 126.39(12) ?
N3 C12 H12 . . 115.4(9) ?
N3 C12 C13 . . 124.16(13) ?
H12 C12 C13 . . 120.4(9) ?
C12 C13 H13 . . 119.4(10) ?
C12 C13 C14 . . 117.42(14) ?
H13 C13 C14 . . 123.2(10) ?
C13 C14 H14 . . 119.8(9) ?
C13 C14 C15 . . 120.38(14) ?
H14 C14 C15 . . 119.8(9) ?
C14 C15 H15 . . 120.4(9) ?
C14 C15 C16 . . 118.60(13) ?
H15 C15 C16 . . 120.9(9) ?
N3 C16 N4 . . 114.41(12) ?
N3 C16 C15 . . 121.77(12) ?
N4 C16 C15 . . 123.79(12) ?
N4 C17 C18 . . 121.58(13) ?
N4 C17 C22 . . 118.64(12) ?
C18 C17 C22 . . 119.76(13) ?
C17 C18 H18 . . 119.0(9) ?
C17 C18 C19 . . 119.53(16) ?
H18 C18 C19 . . 121.4(9) ?
C18 C19 H19 . . 116.3(11) ?
C18 C19 C20 . . 120.70(16) ?
H19 C19 C20 . . 123.0(11) ?
C19 C20 H20 . . 121.6(11) ?
C19 C20 C21 . . 119.73(15) ?
H20 C20 C21 . . 118.6(11) ?
C20 C21 H21 . . 120.4(10) ?
C20 C21 C22 . . 120.21(16) ?
H21 C21 C22 . . 119.3(10) ?
C17 C22 C21 . . 120.07(15) ?
C17 C22 H22 . . 122.0(9) ?
C21 C22 H22 . . 118.0(9) ?
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
Li N1 . 2.036(3) yes
Li N2 . 2.187(3) yes
Li N2 2_666 2.022(3) yes
Li N3 . 2.002(3) yes
N1 C1 . 1.3466(18) ?
N1 C5 . 1.3606(16) ?
N2 Li 2_666 2.022(3) ?
N2 C5 . 1.3718(17) ?
N2 C6 . 1.4035(15) ?
C1 H1 . 0.954(15) ?
C1 C2 . 1.365(2) ?
C2 H2 . 0.962(16) ?
C2 C3 . 1.384(2) ?
C3 H3 . 0.992(17) ?
C3 C4 . 1.371(2) ?
C4 H4 . 0.936(15) ?
C4 C5 . 1.4113(18) ?
C6 C7 . 1.4061(18) ?
C6 C11 . 1.3926(18) ?
C7 H7 . 0.959(17) ?
C7 C8 . 1.376(2) ?
C8 H8 . 0.963(17) ?
C8 C9 . 1.384(2) ?
C9 H9 . 0.969(14) ?
C9 C10 . 1.381(2) ?
C10 H10 . 0.988(17) ?
C10 C11 . 1.3768(19) ?
C11 H11 . 0.916(17) ?
N3 C12 . 1.3465(18) ?
N3 C16 . 1.3481(16) ?
N4 H4N . 0.900(16) ?
N4 C16 . 1.3764(17) ?
N4 C17 . 1.4213(16) ?
C12 H12 . 0.989(14) ?
C12 C13 . 1.372(2) ?
C13 H13 . 0.942(17) ?
C13 C14 . 1.384(2) ?
C14 H14 . 0.991(17) ?
C14 C15 . 1.372(2) ?
C15 H15 . 0.978(14) ?
C15 C16 . 1.3999(18) ?
C17 C18 . 1.3885(19) ?
C17 C22 . 1.385(2) ?
C18 H18 . 0.963(15) ?
C18 C19 . 1.384(2) ?
C19 H19 . 0.934(19) ?
C19 C20 . 1.379(3) ?
C20 H20 . 0.961(18) ?
C20 C21 . 1.378(2) ?
C21 H21 . 0.992(17) ?
C21 C22 . 1.385(2) ?
C22 H22 . 0.988(16) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N4 H4N N2 2_666 0.900(16) 2.288(17) 3.1763(16) 169.1(13) 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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
N2 Li N1 C1 . . 162.8(2)
N2 Li N1 C1 2_666 . -96.1(2)
N2 Li N1 C5 . . 16.23(8)
N2 Li N1 C5 2_666 . 117.34(14)
N3 Li N1 C1 . . 47.9(3)
N3 Li N1 C5 . . -98.63(14)
N1 Li N2 Li . 2_666 112.58(14)
N1 Li N2 C5 . . -16.18(8)
N1 Li N2 C6 . . -142.01(12)
N2 Li N2 Li 2_666 2_666 0.0
N2 Li N2 C5 2_666 . -128.76(14)
N2 Li N2 C6 2_666 . 105.42(15)
N3 Li N2 Li . 2_666 -145.1(2)
N3 Li N2 C5 . . 86.15(15)
N3 Li N2 C6 . . -39.7(2)
Li N1 C1 C2 . . -139.68(19)
C5 N1 C1 C2 . . 1.2(2)
N1 C1 C2 C3 . . -0.3(2)
C1 C2 C3 C4 . . -0.5(2)
C2 C3 C4 C5 . . 0.5(2)
Li N1 C5 N2 . . -26.08(12)
Li N1 C5 C4 . . 156.96(13)
C1 N1 C5 N2 . . 175.75(12)
C1 N1 C5 C4 . . -1.21(19)
Li N2 C5 N1 . . 24.30(12)
Li N2 C5 N1 2_666 . -36.25(17)
Li N2 C5 C4 . . -159.01(15)
Li N2 C5 C4 2_666 . 140.44(14)
C6 N2 C5 N1 . . 159.69(10)
C6 N2 C5 C4 . . -23.63(19)
C3 C4 C5 N1 . . 0.4(2)
C3 C4 C5 N2 . . -176.10(14)
Li N2 C6 C7 . . 73.60(18)
Li N2 C6 C7 2_666 . 157.34(13)
Li N2 C6 C11 . . -102.27(15)
Li N2 C6 C11 2_666 . -18.53(15)
C5 N2 C6 C7 . . -37.35(18)
C5 N2 C6 C11 . . 146.78(12)
N2 C6 C7 C8 . . -177.74(12)
C11 C6 C7 C8 . . -1.82(19)
C6 C7 C8 C9 . . 0.7(2)
C7 C8 C9 C10 . . 0.2(2)
C8 C9 C10 C11 . . 0.1(2)
C9 C10 C11 C6 . . -1.3(2)
N2 C6 C11 C10 . . 178.31(11)
C7 C6 C11 C10 . . 2.13(19)
N1 Li N3 C12 . . 28.69(19)
N1 Li N3 C16 . . -141.62(13)
N2 Li N3 C12 . . -44.9(2)
N2 Li N3 C12 2_666 . 172.62(14)
N2 Li N3 C16 . . 144.76(13)
N2 Li N3 C16 2_666 . 2.3(2)
Li N3 C12 C13 . . -169.80(15)
C16 N3 C12 C13 . . 1.5(2)
N3 C12 C13 C14 . . -1.1(2)
C12 C13 C14 C15 . . -0.5(2)
C13 C14 C15 C16 . . 1.6(2)
Li N3 C16 N4 . . -8.5(2)
Li N3 C16 C15 . . 169.81(14)
C12 N3 C16 N4 . . -178.51(12)
C12 N3 C16 C15 . . -0.25(19)
C17 N4 C16 N3 . . 169.57(12)
C17 N4 C16 C15 . . -8.6(2)
C14 C15 C16 N3 . . -1.3(2)
C14 C15 C16 N4 . . 176.84(13)
C16 N4 C17 C18 . . 58.73(19)
C16 N4 C17 C22 . . -123.15(15)
N4 C17 C18 C19 . . 178.61(14)
C22 C17 C18 C19 . . 0.5(2)
C17 C18 C19 C20 . . -0.3(2)
C18 C19 C20 C21 . . -0.4(3)
C19 C20 C21 C22 . . 0.8(2)
C20 C21 C22 C17 . . -0.6(2)
N4 C17 C22 C21 . . -178.20(13)
C18 C17 C22 C21 . . 0.0(2)
