#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:36:42 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179486 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/83/4338382.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_4338382
loop_
_publ_author_name
'Abrahams, Brendan F.'
'Dharma, A. David'
'Grannas, Martin J.'
'Hudson, Timothy A.'
'Maynard-Casely, Helen E'
'Oliver, Graham R.'
'Robson, Richard'
'White, Keith F.'
_publ_section_title
;
 Isomeric Ionic Lithium Isonicotinate Three-Dimensional Networks and
 Single-Crystal-to-Single-Crystal Rearrangements Generating Microporous
 Materials.
;
_journal_issue                   10
_journal_name_full               'Inorganic chemistry'
_journal_page_first              4956
_journal_page_last               4969
_journal_paper_doi               10.1021/ic403134c
_journal_volume                  53
_journal_year                    2014
_chemical_formula_sum            'C17 H13 Li2 N3 O4'
_chemical_formula_weight         337.18
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 102.790(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.4241(4)
_cell_length_b                   13.8293(9)
_cell_length_c                   11.1181(9)
_cell_measurement_reflns_used    1512
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      74.85
_cell_measurement_theta_min      3.19
_cell_volume                     813.29(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3080
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.943
_diffrn_reflns_theta_min         5.184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.3329
_exptl_crystal_size_mid          0.0406
_exptl_crystal_size_min          0.0387
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0601
_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)+(0.1318P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.1825
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1235
_reflns_number_total             1540
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic403134c_si_002.cif
_cod_data_source_block           Li_inic_pyridine
_cod_depositor_comments
'Adding full bibliography for 4338378--4338389.cif.'
_cod_database_code               4338382
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-1
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.8239(2) 0.04677(10) 0.40884(12) 0.0221(4) Uani 1 1 d . . . . .
N1 N 0.6770(3) 0.31769(12) 0.09896(16) 0.0265(5) Uani 1 1 d . . . . .
O1 O 0.4195(3) 0.08635(12) 0.38962(16) 0.0331(5) Uani 1 1 d . . . . .
C6 C 0.6306(3) 0.09647(14) 0.36576(17) 0.0211(4) Uani 1 1 d . . . . .
C3 C 0.6532(3) 0.17512(14) 0.27395(17) 0.0213(5) Uani 1 1 d . . . . .
C2 C 0.8392(4) 0.17284(15) 0.20564(19) 0.0250(5) Uani 1 1 d . . . . .
H2 H 0.9634 0.1232 0.2186 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5018(4) 0.32024(14) 0.1674(2) 0.0285(5) Uani 1 1 d . . . . .
H5 H 0.3849 0.3724 0.1553 0.034 Uiso 1 1 calc R U . . .
C1 C 0.8397(4) 0.24413(15) 0.11856(19) 0.0267(5) Uani 1 1 d . . . . .
H1 H 0.9631 0.2405 0.0699 0.032 Uiso 1 1 calc R U . . .
C4 C 0.4827(4) 0.25137(15) 0.25404(19) 0.0256(5) Uani 1 1 d . . . . .
H4 H 0.3544 0.2559 0.2997 0.031 Uiso 1 1 calc R U . . .
Li2 Li 1.1829(6) 0.0656(2) 0.4850(3) 0.0214(7) Uani 1 1 d . . . . .
N3S_a N 0.3381(5) -0.0056(3) 1.0764(3) 0.0595(8) Uani 0.5 1 d . . P A 1
C3S_b C 0.3381(5) -0.0056(3) 1.0764(3) 0.0595(8) Uani 0.5 1 d . . P B 2
H3S_b H 0.2266 -0.0107 1.1311 0.071 Uiso 0.5 1 calc R U P B 2
C2S_b C 0.4678(6) 0.0709(2) 0.9156(3) 0.0533(8) Uani 1 1 d . . . B 2
H2S_b H 0.4479 0.1206 0.8553 0.064 Uiso 1 1 calc R U . B 2
C1S_b C 0.3046(5) 0.0661(2) 0.9912(3) 0.0488(7) Uani 1 1 d . . . B 2
H1S_b H 0.1708 0.1114 0.9849 0.059 Uiso 1 1 calc R U . B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C6 O2 Li2 122.60(15) . 3_756
C6 O2 Li2 139.21(16) . .
Li2 O2 Li2 89.67(14) 3_756 .
C1 N1 C5 116.97(17) . .
C1 N1 Li2 126.84(16) . 4_565
C5 N1 Li2 115.98(16) . 4_565
C6 O1 Li2 157.95(19) . 1_455
O1 C6 O2 126.11(18) . .
O1 C6 C3 116.21(17) . .
O2 C6 C3 117.67(16) . .
C4 C3 C2 117.94(17) . .
C4 C3 C6 120.17(16) . .
C2 C3 C6 121.88(17) . .
C1 C2 C3 118.73(18) . .
N1 C5 C4 123.46(18) . .
N1 C1 C2 123.69(18) . .
C5 C4 C3 119.16(18) . .
O1 Li2 O2 125.05(17) 1_655 3_756
O1 Li2 O2 121.30(19) 1_655 .
O2 Li2 O2 90.33(14) 3_756 .
O1 Li2 N1 109.69(17) 1_655 4_666
O2 Li2 N1 104.26(16) 3_756 4_666
O2 Li2 N1 102.74(15) . 4_666
O1 Li2 Li2 140.9(2) 1_655 3_756
O2 Li2 Li2 45.22(10) 3_756 3_756
O2 Li2 Li2 45.10(10) . 3_756
N1 Li2 Li2 109.33(18) 4_666 3_756
C1S_b C2S_b C3S_b 121.7(3) . 3_657
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C6 1.256(2) .
O2 Li2 1.957(3) 3_756
O2 Li2 1.961(3) .
N1 C1 1.333(3) .
N1 C5 1.343(3) .
N1 Li2 2.057(4) 4_565
O1 C6 1.239(2) .
O1 Li2 1.859(3) 1_455
C6 C3 1.515(3) .
C3 C4 1.388(3) .
C3 C2 1.391(3) .
C2 C1 1.382(3) .
C5 C4 1.375(3) .
Li2 O1 1.859(3) 1_655
Li2 O2 1.957(3) 3_756
Li2 N1 2.057(4) 4_666
Li2 Li2 2.762(6) 3_756
C2S_b C1S_b 1.351(5) .
C2S_b C3S_b 1.375(4) 3_657
