data_Li(paa)DMF
_audit_creation_date               2019-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C8 H6 Li N O2'
_chemical_formula_sum              'C8 H6 Li N O2'
_chemical_formula_weight           155.08
_chemical_absolute_configuration   ?
_chemical_melting_point            ?
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'

_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.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             33
_space_group_name_H-M_alt          'P n a 21'
_space_group_name_Hall             'P 2c -2n'
loop_
  _space_group_symop_operation_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'

_cell_length_a                     11.751(4)
_cell_length_b                     18.685(2)
_cell_length_c                     4.9656(4)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1090.3(4)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      1107
_cell_measurement_temperature      130.01(10)
_cell_measurement_theta_max        71.0130
_cell_measurement_theta_min        4.4440
_shelx_estimated_absorpt_T_max     0.982
_shelx_estimated_absorpt_T_min     0.680
_exptl_absorpt_coefficient_mu      0.554
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.11751
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      0.945
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               320
_exptl_crystal_size_max            0.753
_exptl_crystal_size_mid            0.041
_exptl_crystal_size_min            0.033
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.1130
_diffrn_reflns_av_unetI/netI       0.0698
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.991
_diffrn_reflns_limit_h_max         14
_diffrn_reflns_limit_h_min         -13
_diffrn_reflns_limit_k_max         23
_diffrn_reflns_limit_k_min         -23
_diffrn_reflns_limit_l_max         6
_diffrn_reflns_limit_l_min         -3
_diffrn_reflns_number              8252
_diffrn_reflns_point_group_measured_fraction_full  0.836
_diffrn_reflns_point_group_measured_fraction_max  0.813
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           73.954
_diffrn_reflns_theta_min           4.445
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        130.01(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   10.2273
_diffrn_detector_type              Atlas
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -31.00   6.00   1.00   30.00    --  -41.87 112.00  65.00   37
  2  ω    -66.00  32.00   1.00   30.00    --  -41.87  38.00   0.00   98
  3  ω    -63.00  31.00   1.00   30.00    --  -41.87  38.00  60.00   94
  4  ω     17.00 116.00   1.00   30.00    --   41.87  38.00  30.00   99
  5  ω     61.00  88.00   1.00   30.00    --   41.87-125.00  30.00   27
  6  ω     18.00  80.00   1.00   30.00    --   41.87 -99.00 150.00   62
  7  ω     86.00 116.00   1.00   30.00    --  105.57-125.00 120.00   30
  8  ω     57.00 109.00   1.00   30.00    --  105.57 -94.00 -30.00   52
  9  ω     69.00 172.00   1.00   30.00    --  105.57  15.00 -60.00  103
 10  ω    130.00 158.00   1.00   30.00    --  105.57 -15.00   0.00   28
 11  ω     86.00 154.00   1.00   30.00    --  105.57  45.00-150.00   68
 12  ω     56.00 122.00   1.00   30.00    --  105.57-125.00 -90.00   66
 13  ω     34.00 103.00   1.00   30.00    --  105.57 -61.00   0.00   69
 14  ω     32.00  59.00   1.00   30.00    --  105.57 -30.00-120.00   27
 15  ω     24.00  75.00   1.00   30.00    --  105.57 -15.00   0.00   51
 16  ω     82.00 128.00   1.00   30.00    --  105.57 -30.00-120.00   46
 17  ω     29.00 132.00   1.00   30.00    --  105.57 -30.00  90.00  103
 18  ω     82.00 109.00   1.00   30.00    --  105.57 -15.00   0.00   27
 19  ω     27.00  92.00   1.00   30.00    --  105.57 -94.00 -90.00   65
 20  ω     38.00  71.00   1.00   30.00    --  105.57 -45.00 -90.00   33
 21  ω     29.00 127.00   1.00   30.00    --  105.57 -77.00  90.00   98
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0389861000
_diffrn_orient_matrix_UB_12        0.0102474000
_diffrn_orient_matrix_UB_13        0.0764039000
_diffrn_orient_matrix_UB_21        0.1234692000
_diffrn_orient_matrix_UB_22        -0.0039635000
_diffrn_orient_matrix_UB_23        0.0267252000
_diffrn_orient_matrix_UB_31        0.0209538000
_diffrn_orient_matrix_UB_32        0.0428908000
_diffrn_orient_matrix_UB_33        -0.0158470000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage           0.463
_reflns_Friedel_fraction_full      0.625
_reflns_Friedel_fraction_max       0.586
_reflns_number_gt                  843
_reflns_number_total               1797
_reflns_odcompleteness_completeness  97.97
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       66.97
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection         'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction          'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.135
_refine_diff_density_min           -0.289
_refine_diff_density_rms           0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 165 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.3(9)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     0.965
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       109
_refine_ls_number_reflns           1797
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.1468
_refine_ls_R_factor_gt             0.0980
_refine_ls_restrained_S_all        0.964
_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)+(0.1895P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.2710
_refine_ls_wR_factor_ref           0.3242
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C2(H2), C1(H1), C3(H3)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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
 O1 O 0.5812(5) 0.47285(19) 0.6676(10) 0.0897(17) Uani 1 1 d . . . . .
 O2 O 0.6154(6) 0.4199(3) 0.2770(10) 0.115(3) Uani 1 1 d . . . . .
 N1 N 0.9110(9) 0.1348(3) 0.8987(17) 0.120(3) Uani 1 1 d . . . . .
 C8 C 0.6244(8) 0.4220(3) 0.5281(14) 0.086(2) Uani 1 1 d . . . . .
 C7 C 0.6876(9) 0.3674(4) 0.6698(17) 0.107(3) Uani 1 1 d . . . . .
 H7 H 0.7096 0.3758 0.8469 0.128 Uiso 1 1 calc R . . . .
 C4 C 0.7812(10) 0.2465(3) 0.6777(16) 0.110(3) Uani 1 1 d . . . . .
 C6 C 0.7160(10) 0.3035(4) 0.5515(13) 0.114(4) Uani 1 1 d . . . . .
 H6 H 0.6916 0.2960 0.3756 0.137 Uiso 1 1 calc R . . . .
 C5 C 0.8511(12) 0.2568(4) 0.885(2) 0.152(5) Uani 1 1 d . . . . .
 H5 H 0.8574 0.3020 0.9625 0.183 Uiso 1 1 calc R . . . .
 C2 C 0.8419(13) 0.1241(5) 0.691(3) 0.175(7) Uani 1 1 d . . . . .
 H2 H 0.8347 0.0780 0.6225 0.209 Uiso 1 1 calc R . . . .
 C1 C 0.9167(13) 0.1982(4) 0.989(2) 0.145(5) Uani 1 1 d . . . . .
 H1 H 0.9663 0.2072 1.1310 0.174 Uiso 1 1 calc R . . . .
 C3 C 0.7779(14) 0.1805(5) 0.568(2) 0.158(6) Uani 1 1 d . . . . .
 H3 H 0.7347 0.1717 0.4140 0.190 Uiso 1 1 calc R . . . .
 Li1 Li 0.5111(17) 0.4526(6) 0.020(2) 0.102(5) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
 O1 C8 1.281(8) . ?
 O1 Li1 1.912(14) 2_665 ?
 O1 Li1 1.970(14) 1_556 ?
 O2 C8 1.252(8) . ?
 O2 Li1 1.872(16) . ?
 N1 C2 1.328(16) . ?
 N1 C1 1.269(10) . ?
 N1 Li1 2.101(16) 3_556 ?
 C8 C7 1.445(11) . ?
 C7 H7 0.9300 . ?
 C7 C6 1.372(10) . ?
 C4 C6 1.453(10) . ?
 C4 C5 1.331(14) . ?
 C4 C3 1.351(11) . ?
 C6 H6 0.9300 . ?
 C5 H5 0.9300 . ?
 C5 C1 1.436(12) . ?
 C2 H2 0.9300 . ?
 C2 C3 1.431(15) . ?
 C1 H1 0.9300 . ?
 C3 H3 0.9300 . ?
 Li1 O1 1.912(14) 2_664 ?
 Li1 O1 1.970(14) 1_554 ?
 Li1 N1 2.101(16) 3_454 ?
 Li1 Li1 3.061(12) 2_665 ?
 Li1 Li1 3.061(12) 2_664 ?

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
 C8 O1 Li1 123.9(6) . 2_665 ?
 C8 O1 Li1 120.3(5) . 1_556 ?
 Li1 O1 Li1 104.1(4) 2_665 1_556 ?
 C8 O2 Li1 136.4(7) . . ?
 C2 N1 Li1 116.7(6) . 3_556 ?
 C1 N1 C2 116.6(8) . . ?
 C1 N1 Li1 126.5(9) . 3_556 ?
 O1 C8 C7 117.6(7) . . ?
 O2 C8 O1 121.9(7) . . ?
 O2 C8 C7 120.4(7) . . ?
 C8 C7 H7 119.0 . . ?
 C6 C7 C8 122.1(8) . . ?
 C6 C7 H7 119.0 . . ?
 C5 C4 C6 123.6(7) . . ?
 C5 C4 C3 117.6(8) . . ?
 C3 C4 C6 118.6(9) . . ?
 C7 C6 C4 125.5(7) . . ?
 C7 C6 H6 117.2 . . ?
 C4 C6 H6 117.2 . . ?
 C4 C5 H5 120.0 . . ?
 C4 C5 C1 120.0(8) . . ?
 C1 C5 H5 120.0 . . ?
 N1 C2 H2 118.5 . . ?
 N1 C2 C3 122.9(9) . . ?
 C3 C2 H2 118.5 . . ?
 N1 C1 C5 123.8(11) . . ?
 N1 C1 H1 118.1 . . ?
 C5 C1 H1 118.1 . . ?
 C4 C3 C2 118.9(11) . . ?
 C4 C3 H3 120.5 . . ?
 C2 C3 H3 120.5 . . ?
 O1 Li1 O1 116.0(6) 2_664 1_554 ?
 O1 Li1 N1 111.0(10) 2_664 3_454 ?
 O1 Li1 N1 97.4(5) 1_554 3_454 ?
 O1 Li1 Li1 80.9(6) 2_664 2_664 ?
 O1 Li1 Li1 130.2(8) 1_554 2_665 ?
 O1 Li1 Li1 38.6(4) 2_664 2_665 ?
 O1 Li1 Li1 37.3(3) 1_554 2_664 ?
 O2 Li1 O1 113.2(10) . 1_554 ?
 O2 Li1 O1 110.3(5) . 2_664 ?
 O2 Li1 N1 107.9(6) . 3_454 ?
 O2 Li1 Li1 72.0(4) . 2_665 ?
 O2 Li1 Li1 142.9(12) . 2_664 ?
 N1 Li1 Li1 99.8(6) 3_454 2_664 ?
 N1 Li1 Li1 129.3(10) 3_454 2_665 ?
 Li1 Li1 Li1 108.4(6) 2_664 2_665 ?

_smtbx_masks_special_details       ?
loop_
  _smtbx_masks_void_nr
  _smtbx_masks_void_average_x
  _smtbx_masks_void_average_y
  _smtbx_masks_void_average_z
  _smtbx_masks_void_volume
  _smtbx_masks_void_count_electrons
  _smtbx_masks_void_content
 1 0.000 0.500 -0.397 212.7 64.9 ?
 2 0.500 1.000 -0.462 212.7 64.9 ?

_olex2_date_sample_data_collection  2016-05-13
_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  8.345
_oxdiff_exptl_absorpt_empirical_full_min  0.296
