#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:35:12 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179797 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/93/7009390.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_7009390
loop_
_publ_author_name
'Clegg, William'
'Horsburgh, Lynne'
'Liddle, Stephen T.'
'Mackenzie, Fiona M.'
'Mulvey, Robert E.'
'Robertson, Alan'
_publ_section_title
;
 The changing structural chemistry of lithium anilide on solvation by
 pyridine, 4-methylpyridine or 4-tert-butylpyridine
;
_journal_issue                   7
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              1225
_journal_paper_doi               10.1039/b000576m
_journal_year                    2000
_chemical_formula_sum            'C32 H32 Li2 N6'
_chemical_formula_weight         514.52
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.104(3)
_cell_length_b                   11.5602(16)
_cell_length_c                   14.2505(19)
_cell_measurement_reflns_used    6745
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      24.45
_cell_measurement_theta_min      2.09
_cell_volume                     2982.4(8)
_computing_cell_refinement       'local programs'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.905
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12310
_diffrn_reflns_theta_full        25.61
_diffrn_reflns_theta_max         25.61
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_coef       0.0060(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4291
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²+1.4354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1594
_reflns_number_gt                3767
_reflns_number_total             4291
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b000576m.txt
_cod_data_source_block           (1)
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7009390
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Li1 Li 0.0844(3) -0.0547(5) 0.2525(4) 0.0528(14) Uani 1 1 d . . .
Li2 Li 0.1980(3) 0.0013(5) 0.1614(4) 0.0476(13) Uani 1 1 d . . .
N1 N 0.1154(2) -0.1056(3) 0.1229(2) 0.0714(10) Uani 1 1 d D . .
H1N H 0.085(2) -0.070(4) 0.082(3) 0.086 Uiso 1 1 d D . .
C1 C 0.1165(2) -0.2125(3) 0.0791(3) 0.0570(10) Uani 1 1 d . . .
C2 C 0.0761(2) -0.2348(3) 0.0005(3) 0.0600(10) Uani 1 1 d . . .
H2 H 0.0463 -0.1745 -0.0243 0.072 Uiso 1 1 calc R . .
C3 C 0.0761(2) -0.3391(4) -0.0445(3) 0.0648(11) Uani 1 1 d . . .
H3 H 0.0474 -0.3482 -0.0998 0.078 Uiso 1 1 calc R . .
C4 C 0.1167(3) -0.4316(4) -0.0118(4) 0.0695(13) Uani 1 1 d . . .
H4 H 0.1159 -0.5047 -0.0422 0.083 Uiso 1 1 calc R . .
C5 C 0.1594(2) -0.4121(4) 0.0689(4) 0.0725(14) Uani 1 1 d . . .
H5 H 0.1892 -0.4722 0.0940 0.087 Uiso 1 1 calc R . .
C6 C 0.1579(2) -0.3035(5) 0.1121(3) 0.0693(13) Uani 1 1 d . . .
H6 H 0.1870 -0.2921 0.1669 0.083 Uiso 1 1 calc R . .
N2 N 0.16217(17) 0.0604(2) 0.28889(19) 0.0511(7) Uani 1 1 d D . .
H2N H 0.1912(17) 0.029(3) 0.3333(19) 0.061 Uiso 1 1 d D . .
C7 C 0.16102(18) 0.1779(3) 0.2995(3) 0.0470(8) Uani 1 1 d . . .
C8 C 0.11967(19) 0.2459(4) 0.2375(4) 0.0718(13) Uani 1 1 d . . .
H8 H 0.0912 0.2089 0.1903 0.086 Uiso 1 1 calc R . .
C9 C 0.1191(3) 0.3653(5) 0.2428(7) 0.117(3) Uani 1 1 d . . .
H9 H 0.0908 0.4086 0.1989 0.140 Uiso 1 1 calc R . .
C10 C 0.1588(5) 0.4218(5) 0.3107(8) 0.134(4) Uani 1 1 d . . .
H10 H 0.1575 0.5038 0.3150 0.161 Uiso 1 1 calc R . .
C11 C 0.2005(4) 0.3579(5) 0.3726(5) 0.111(2) Uani 1 1 d . . .
H11 H 0.2289 0.3965 0.4191 0.134 Uiso 1 1 calc R . .
C12 C 0.2018(3) 0.2383(4) 0.3683(3) 0.0668(11) Uani 1 1 d . . .
H12 H 0.2306 0.1962 0.4123 0.080 Uiso 1 1 calc R . .
N3 N 0.06217(17) -0.1683(3) 0.3609(2) 0.0530(8) Uani 1 1 d . . .
C13 C 0.0627(2) -0.2840(3) 0.3554(3) 0.0647(11) Uani 1 1 d . . .
H13 H 0.0769 -0.3190 0.2978 0.078 Uiso 1 1 calc R . .
C14 C 0.0438(3) -0.3542(4) 0.4293(4) 0.0830(14) Uani 1 1 d . . .
H14 H 0.0465 -0.4360 0.4236 0.100 Uiso 1 1 calc R . .
C15 C 0.0210(4) -0.3045(5) 0.5106(4) 0.1018(19) Uani 1 1 d . . .
H15 H 0.0061 -0.3511 0.5621 0.122 Uiso 1 1 calc R . .
C16 C 0.0199(3) -0.1859(4) 0.5176(3) 0.0920(17) Uani 1 1 d . . .
H16 H 0.0045 -0.1491 0.5738 0.110 Uiso 1 1 calc R . .
C17 C 0.0414(3) -0.1231(4) 0.4425(3) 0.0698(12) Uani 1 1 d . . .
H17 H 0.0416 -0.0413 0.4484 0.084 Uiso 1 1 calc R . .
N4 N 0.20943(16) 0.1136(3) 0.0461(2) 0.0557(8) Uani 1 1 d . . .
C18 C 0.1753(3) 0.1026(4) -0.0331(3) 0.0754(13) Uani 1 1 d . . .
H18 H 0.1432 0.0384 -0.0409 0.091 Uiso 1 1 calc R . .
C19 C 0.1831(4) 0.1792(6) -0.1074(4) 0.112(2) Uani 1 1 d . . .
H19 H 0.1572 0.1662 -0.1644 0.135 Uiso 1 1 calc R . .
C20 C 0.2275(3) 0.2726(4) -0.0984(4) 0.0818(14) Uani 1 1 d . . .
H20 H 0.2334 0.3266 -0.1480 0.098 Uiso 1 1 calc R . .
C21 C 0.2621(3) 0.2854(5) -0.0185(4) 0.0924(17) Uani 1 1 d . . .
H21 H 0.2934 0.3503 -0.0088 0.111 Uiso 1 1 calc R . .
C22 C 0.2529(3) 0.2044(5) 0.0516(4) 0.0967(18) Uani 1 1 d . . .
H22 H 0.2800 0.2151 0.1080 0.116 Uiso 1 1 calc R . .
N5 N 0.30651(16) -0.0537(3) 0.1770(2) 0.0528(8) Uani 1 1 d . . .
C23 C 0.3317(2) -0.1252(3) 0.1118(3) 0.0597(10) Uani 1 1 d . . .
H23 H 0.2968 -0.1674 0.0758 0.072 Uiso 1 1 calc R . .
C24 C 0.4058(2) -0.1419(3) 0.0932(3) 0.0560(10) Uani 1 1 d . . .
H24 H 0.4211 -0.1909 0.0434 0.067 Uiso 1 1 calc R . .
C25 C 0.4564(2) -0.0871(4) 0.1474(3) 0.0592(10) Uani 1 1 d . . .
H25 H 0.5078 -0.0982 0.1377 0.071 Uiso 1 1 calc R . .
C26 C 0.4308(2) -0.0145(4) 0.2172(3) 0.0621(10) Uani 1 1 d . . .
H26 H 0.4646 0.0249 0.2570 0.074 Uiso 1 1 calc R . .
C27 C 0.35635(19) 0.0004(3) 0.2287(3) 0.0553(9) Uani 1 1 d . . .
H27 H 0.3397 0.0519 0.2761 0.066 Uiso 1 1 calc R . .
N6 N -0.02217(16) 0.0058(3) 0.2262(2) 0.0575(8) Uani 1 1 d . . .
C28 C -0.0525(2) 0.0969(4) 0.2695(3) 0.0616(10) Uani 1 1 d . . .
H28 H -0.0221 0.1426 0.3093 0.074 Uiso 1 1 calc R . .
C29 C -0.1254(2) 0.1278(4) 0.2594(3) 0.0690(11) Uani 1 1 d . . .
H29 H -0.1450 0.1935 0.2908 0.083 Uiso 1 1 calc R . .
C30 C -0.1691(2) 0.0608(5) 0.2023(3) 0.0749(13) Uani 1 1 d . . .
H30 H -0.2198 0.0793 0.1946 0.090 Uiso 1 1 calc R . .
C31 C -0.1397(2) -0.0326(4) 0.1567(4) 0.0744(13) Uani 1 1 d . . .
H31 H -0.1692 -0.0790 0.1164 0.089 Uiso 1 1 calc R . .
C32 C -0.0662(2) -0.0572(4) 0.1708(3) 0.0673(11) Uani 1 1 d . . .
H32 H -0.0457 -0.1223 0.1396 0.081 Uiso 1 1 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Li1 N1 103.6(3) . . ?
N2 Li1 N3 111.4(3) . . ?
N1 Li1 N3 123.6(3) . . ?
N2 Li1 N6 118.2(3) . . ?
N1 Li1 N6 101.0(3) . . ?
N3 Li1 N6 99.6(3) . . ?
N1 Li2 N2 102.2(3) . . ?
N1 Li2 N5 122.9(3) . . ?
N2 Li2 N5 107.9(3) . . ?
N1 Li2 N4 103.8(3) . . ?
N2 Li2 N4 121.2(3) . . ?
N5 Li2 N4 100.3(3) . . ?
C1 N1 Li2 131.3(3) . . ?
C1 N1 Li1 132.5(4) . . ?
Li2 N1 Li1 77.2(3) . . ?
C2 C1 C6 115.4(4) . . ?
C2 C1 N1 122.1(4) . . ?
C6 C1 N1 122.4(4) . . ?
C1 C2 C3 123.6(4) . . ?
C2 C3 C4 121.7(4) . . ?
C3 C4 C5 116.4(4) . . ?
C6 C5 C4 119.7(4) . . ?
C1 C6 C5 123.1(4) . . ?
C7 N2 Li1 132.7(3) . . ?
C7 N2 Li2 115.8(3) . . ?
Li1 N2 Li2 76.8(3) . . ?
N2 C7 C8 119.7(4) . . ?
N2 C7 C12 124.1(4) . . ?
C8 C7 C12 116.1(4) . . ?
C9 C8 C7 122.0(6) . . ?
C10 C9 C8 120.7(6) . . ?
C9 C10 C11 119.0(5) . . ?
C10 C11 C12 121.1(7) . . ?
C11 C12 C7 121.1(5) . . ?
C17 N3 C13 116.4(4) . . ?
C17 N3 Li1 117.4(3) . . ?
C13 N3 Li1 126.1(3) . . ?
N3 C13 C14 122.9(4) . . ?
C15 C14 C13 118.7(4) . . ?
C14 C15 C16 119.2(5) . . ?
C17 C16 C15 118.3(4) . . ?
N3 C17 C16 124.3(4) . . ?
C18 N4 C22 114.6(4) . . ?
C18 N4 Li2 125.0(3) . . ?
C22 N4 Li2 120.3(3) . . ?
N4 C18 C19 123.7(5) . . ?
C20 C19 C18 119.8(5) . . ?
C21 C20 C19 117.3(5) . . ?
C20 C21 C22 119.7(5) . . ?
N4 C22 C21 124.8(5) . . ?
C27 N5 C23 116.8(3) . . ?
C27 N5 Li2 124.1(3) . . ?
C23 N5 Li2 116.2(3) . . ?
N5 C23 C24 123.8(4) . . ?
C25 C24 C23 118.8(4) . . ?
C24 C25 C26 117.9(3) . . ?
C27 C26 C25 119.5(4) . . ?
N5 C27 C26 123.1(4) . . ?
C32 N6 C28 117.1(3) . . ?
C32 N6 Li1 118.3(3) . . ?
C28 N6 Li1 124.1(3) . . ?
N6 C28 C29 123.3(4) . . ?
C30 C29 C28 117.9(4) . . ?
C31 C30 C29 120.3(4) . . ?
C30 C31 C32 118.0(4) . . ?
N6 C32 C31 123.4(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Li1 N2 2.005(6) . ?
Li1 N1 2.018(7) . ?
Li1 N3 2.067(7) . ?
Li1 N6 2.087(7) . ?
Li2 N1 2.016(7) . ?
Li2 N2 2.046(7) . ?
Li2 N5 2.076(7) . ?
Li2 N4 2.105(7) . ?
N1 C1 1.385(5) . ?
C1 C2 1.362(6) . ?
C1 C6 1.375(6) . ?
C2 C3 1.366(6) . ?
C3 C4 1.379(6) . ?
C4 C5 1.404(7) . ?
C5 C6 1.398(7) . ?
N2 C7 1.367(4) . ?
C7 C8 1.400(5) . ?
C7 C12 1.412(6) . ?
C8 C9 1.382(8) . ?
C9 C10 1.371(11) . ?
C10 C11 1.377(11) . ?
C11 C12 1.384(7) . ?
N3 C17 1.330(5) . ?
N3 C13 1.340(5) . ?
C13 C14 1.373(6) . ?
C14 C15 1.357(7) . ?
C15 C16 1.375(7) . ?
C16 C17 1.350(6) . ?
N4 C18 1.293(5) . ?
N4 C22 1.314(5) . ?
C18 C19 1.387(7) . ?
C19 C20 1.352(8) . ?
C20 C21 1.307(7) . ?
C21 C22 1.379(7) . ?
N5 C27 1.322(5) . ?
N5 C23 1.324(5) . ?
C23 C24 1.381(5) . ?
C24 C25 1.355(6) . ?
C25 C26 1.382(6) . ?
C26 C27 1.369(5) . ?
N6 C32 1.337(5) . ?
N6 C28 1.339(5) . ?
C28 C29 1.376(6) . ?
C29 C30 1.373(6) . ?
C30 C31 1.367(7) . ?
C31 C32 1.376(6) . ?
