#------------------------------------------------------------------------------
#$Date: 2022-09-21 18:44:46 +0300 (Wed, 21 Sep 2022) $
#$Revision: 278046 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/37/7223763.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_7223763
loop_
_publ_author_name
'Tominaka, Satoshi'
'Yeung, Hamish H.-M.'
'Henke, Sebastian'
'Cheetham, Anthony K.'
_publ_section_title
;
 Coordination environments and π-conjugation in dense lithium
 coordination polymers
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              398
_journal_paper_doi               10.1039/C5CE01658D
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H8 Li N O6'
_chemical_formula_sum            'C14 H8 Li N O6'
_chemical_formula_weight         293.16
_chemical_name_systematic        'Lithium 1-hydroxy-4-nitroanthraquinone'
_chemical_properties_physical
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8535(3)
_cell_length_b                   13.0952(10)
_cell_length_c                   18.9644(12)
_cell_measurement_reflns_used    1526
_cell_measurement_temperature    120
_cell_measurement_theta_max      61.1950
_cell_measurement_theta_min      4.1025
_cell_volume                     1205.33(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega -110.00  -62.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -      -31.9956  178.0000 -120.0000 48

  2 omega -110.00  -81.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -      -31.9956 -178.0000   90.0000 29

  3 omega   57.00   87.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -       31.9956   57.0000   30.0000 30

  4 omega   -6.00   52.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -       31.9956  -57.0000   60.0000 58

  5 omega -133.00 -105.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -      -75.0000 -111.0000  120.0000 28

  6 omega   19.00   61.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  -30.0000  -30.0000 42

  7 omega   97.00  124.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  111.0000   90.0000 27

  8 omega   53.00   84.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  -94.0000  -90.0000 31

  9 omega   17.00   49.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  -94.0000  -90.0000 32

 10 omega   22.00  110.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  -61.0000   30.0000 88

 11 omega   45.00   77.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  -94.0000 -150.0000 32

 12 omega   10.00  101.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -       31.9956   57.0000 -150.0000 91

 13 omega    5.00  105.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -       31.9956   37.0000  120.0000 100

 14 omega   10.00  101.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -       31.9956   57.0000  -30.0000 91

 15 omega   58.00  100.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409   77.0000  -30.0000 42
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0722835000
_diffrn_orient_matrix_UB_12      -0.0934764000
_diffrn_orient_matrix_UB_13      0.0457931000
_diffrn_orient_matrix_UB_21      -0.1631037000
_diffrn_orient_matrix_UB_22      -0.0692716000
_diffrn_orient_matrix_UB_23      -0.0504951000
_diffrn_orient_matrix_UB_31      0.2626732000
_diffrn_orient_matrix_UB_32      -0.0174677000
_diffrn_orient_matrix_UB_33      -0.0441221000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3296
_diffrn_reflns_theta_full        61.20
_diffrn_reflns_theta_max         61.20
_diffrn_reflns_theta_min         4.10
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.6154
_exptl_crystal_description       needle
_exptl_crystal_F_000             602.2935
_exptl_crystal_size_max          0.5977
_exptl_crystal_size_mid          0.0244
_exptl_crystal_size_min          0.0143
_refine_diff_density_max         0.4194
_refine_diff_density_min         -0.3751
_refine_diff_density_rms         0.0559
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_d_res_high            0.8798
_refine_ls_d_res_low             10.7758
_refine_ls_goodness_of_fit_ref   1.0713
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    15
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0713
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0754P)²+0.7875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.700
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              21
_reflns_limit_l_min              -20
_reflns_number_gt                1486
_reflns_number_total             1625
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ce01658d2.cif
_cod_data_source_block           6_Li-14hnaq_120K
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7223763
_chemical_oxdiff_formula         'Li C14 O6 N H8'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.2(3) -0.2(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Riding coordinates:
 O6(H6a,H6b)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C12(H12), C11(H11), C13(H13), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,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_refinement_flags_posn
O5 O 0.4779(5) 0.29502(17) 0.55535(11) 0.0252(6) Uani 1.000000 .
O4 O 0.9141(5) 0.40486(18) 0.50671(12) 0.0277(6) Uani 1.000000 .
O3 O 0.9803(8) 0.5966(2) 0.75600(15) 0.0529(8) Uani 1.000000 .
O6 O 0.4172(5) 0.34949(19) 0.40260(12) 0.0315(6) Uani 1.000000 .
H6a H 0.4823(5) 0.40059(19) 0.38050(12) 0.0473(9) Uiso 1.000000 R
H6b H 0.2710(5) 0.36709(19) 0.42410(12) 0.0473(9) Uiso 1.000000 R
O1 O 0.8699(10) 0.4302(3) 0.84979(18) 0.0758(12) Uani 1.000000 .
O2 O 0.5089(8) 0.5213(6) 0.8453(3) 0.151(3) Uani 1.000000 .
N1 N 0.6674(7) 0.4652(3) 0.81919(19) 0.0445(9) Uani 1.000000 .
C6 C 0.9145(6) 0.4487(3) 0.56481(18) 0.0227(7) Uani 1.000000 .
C5 C 1.1121(6) 0.5350(3) 0.57416(18) 0.0233(7) Uani 1.000000 .
C8 C 0.7346(6) 0.4184(2) 0.62290(17) 0.0210(7) Uani 1.000000 .
C1 C 0.6192(7) 0.4308(3) 0.74636(18) 0.0255(7) Uani 1.000000 .
C4 C 1.1386(7) 0.5835(3) 0.63952(19) 0.0271(8) Uani 1.000000 .
C3 C 0.9688(7) 0.5509(3) 0.69996(19) 0.0287(8) Uani 1.000000 .
C10 C 0.4108(6) 0.3577(3) 0.73896(18) 0.0257(8) Uani 1.000000 .
H10 H 0.3008(6) 0.3387(3) 0.77825(18) 0.0308(9) Uiso 1.000000 R
C9 C 0.3679(7) 0.3143(3) 0.67454(17) 0.0254(8) Uani 1.000000 .
H9 H 0.2265(7) 0.2646(3) 0.66977(17) 0.0304(9) Uiso 1.000000 R
C12 C 1.4612(7) 0.6454(3) 0.52593(19) 0.0299(8) Uani 1.000000 .
H12 H 1.5723(7) 0.6665(3) 0.48732(19) 0.0358(9) Uiso 1.000000 R
C7 C 0.5281(7) 0.3407(2) 0.61381(17) 0.0233(7) Uani 1.000000 .
C2 C 0.7740(7) 0.4642(3) 0.69030(18) 0.0248(7) Uani 1.000000 .
C11 C 1.2748(7) 0.5662(3) 0.51774(19) 0.0276(8) Uani 1.000000 .
H11 H 1.2580(7) 0.5331(3) 0.47338(19) 0.0331(9) Uiso 1.000000 R
C13 C 1.4857(8) 0.6945(3) 0.5914(2) 0.0331(8) Uani 1.000000 .
H13 H 1.6120(8) 0.7493(3) 0.5969(2) 0.0398(10) Uiso 1.000000 R
C14 C 1.3273(7) 0.6633(3) 0.64760(18) 0.0306(8) Uani 1.000000 .
H14 H 1.3462(7) 0.6962(3) 0.69201(18) 0.0368(10) Uiso 1.000000 R
Li1 Li 0.6842(12) 0.3021(4) 0.4698(3) 0.0304(13) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32300 0.14000 0.04100 10.51100 26.12600 3.14200
57.80000 0.003 'Custom 4-Gaussian' custom
C 0.01800 0.00900 2.31000 1.02000 1.58900 0.86500 20.84400 10.20800 0.56900
51.65100 0.216 'Custom 4-Gaussian' custom
Li 0.00100 0.00000 1.12800 0.75100 0.61800 0.46500 3.95500 1.05200 85.39100
168.26100 0.038 'Custom 4-Gaussian' custom
O 0.04900 0.03200 3.04900 2.28700 1.54600 0.86700 13.27700 5.70100 0.32400
32.90900 0.251 'Custom 4-Gaussian' custom
N 0.03100 0.01800 12.21300 3.13200 2.01300 1.16600 0.00600 9.89300 28.99800
0.58300 -11.529 'Custom 4-Gaussian' custom
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 8 -4 0.0198 0.0015 7.9954 -3.9893 -0.9300 -0.3527 0.0367
0 -8 4 0.0010 -0.0015 -7.9954 3.9893 0.9300 0.3527 -0.0367
0 -1 -12 0.0125 0.0057 -1.0038 -11.9927 -0.4549 0.6742 0.5482
3 -1 0 0.3214 3.0020 -1.0008 0.0002 0.3106 -0.4203 0.8060
-3 1 0 0.2684 -3.0020 1.0008 -0.0002 -0.3106 0.4203 -0.8060
0 1 12 0.0018 -0.0057 1.0038 11.9927 0.4549 -0.6742 -0.5482
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
Li1 O5 C7 130.4(3) 2_456 .
Li1 O5 C7 127.8(3) . .
Li1 O4 C6 131.4(3) . .
H6b O6 H6a 109.5 . .
Li1 O6 H6a 109.3 . .
Li1 O6 H6b 109.4 . .
O2 N1 O1 123.9(4) . .
C1 N1 O1 117.1(4) . .
C1 N1 O2 118.9(4) . .
C5 C6 O4 117.1(3) . .
C8 C6 O4 122.9(3) . .
C8 C6 C5 120.0(3) . .
C4 C5 C6 120.5(3) . .
C11 C5 C6 119.8(3) . .
C11 C5 C4 119.7(3) . .
C7 C8 C6 121.2(3) . .
C2 C8 C6 118.8(3) . .
C2 C8 C7 119.9(3) . .
C10 C1 N1 114.7(3) . .
C2 C1 N1 122.9(3) . .
C2 C1 C10 122.4(3) . .
C3 C4 C5 120.4(3) . .
C14 C4 C5 119.8(3) . .
C14 C4 C3 119.8(3) . .
C4 C3 O3 120.6(3) . .
C2 C3 O3 120.7(3) . .
C2 C3 C4 118.7(3) . .
H10 C10 C1 120.5(2) . .
C9 C10 C1 119.0(3) . .
C9 C10 H10 120.5(2) . .
H9 C9 C10 118.8(2) . .
C7 C9 C10 122.5(3) . .
C7 C9 H9 118.77(18) . .
C11 C12 H12 120.1(2) . .
C13 C12 H12 120.1(2) . .
C13 C12 C11 119.8(3) . .
C8 C7 O5 124.4(3) . .
C9 C7 O5 118.6(3) . .
C9 C7 C8 116.9(3) . .
C1 C2 C8 119.1(3) . .
C3 C2 C8 121.1(3) . .
C3 C2 C1 119.7(3) . .
C12 C11 C5 120.3(3) . .
H11 C11 C5 119.8(2) . .
H11 C11 C12 119.8(2) . .
H13 C13 C12 119.9(2) . .
C14 C13 C12 120.2(3) . .
C14 C13 H13 119.9(2) . .
C13 C14 C4 120.2(3) . .
H14 C14 C4 119.9(2) . .
H14 C14 C13 119.9(2) . .
O4 Li1 O5 97.0(3) . 2_556
O4 Li1 O5 91.7(3) . .
O6 Li1 O5 122.5(3) . 2_556
O6 Li1 O5 103.0(3) . .
O6 Li1 O4 114.6(3) . .
Li1 Li1 O5 112.5(3) 2_456 2_556
Li1 Li1 O5 39.79(18) 2_456 .
Li1 Li1 O5 94.4(3) 2_556 .
Li1 Li1 O5 38.35(13) 2_556 2_556
Li1 Li1 O4 72.8(2) 2_556 .
Li1 Li1 O4 131.3(4) 2_456 .
Li1 Li1 O6 160.6(4) 2_556 .
Li1 Li1 O6 81.66(16) 2_456 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O5 C7 1.283(4) .
O5 Li1 1.969(6) 2_456
O5 Li1 1.909(6) .
O4 C6 1.242(4) .
O4 Li1 1.883(6) .
O3 C3 1.221(4) .
O6 H6a 0.8505 .
O6 H6b 0.8502 .
O6 Li1 1.920(6) .
O1 N1 1.230(5) .
O2 N1 1.174(5) .
N1 C1 1.471(5) .
C6 C5 1.493(5) .
C6 C8 1.461(5) .
C5 C4 1.399(5) .
C5 C11 1.391(5) .
C8 C7 1.439(5) .
C8 C2 1.425(5) .
C1 C10 1.400(5) .
C1 C2 1.373(5) .
C4 C3 1.475(5) .
C4 C14 1.399(5) .
C3 C2 1.488(5) .
C10 H10 0.9500 .
C10 C9 1.364(5) .
C9 H9 0.9500 .
C9 C7 1.432(5) .
C12 H12 0.9500 .
C12 C11 1.385(5) .
C12 C13 1.402(5) .
C11 H11 0.9500 .
C13 H13 0.9500 .
C13 C14 1.377(5) .
C14 H14 0.9500 .
Li1 Li1 3.011(7) 2_456
Li1 Li1 3.011(7) 2_556
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.2(3)
2 -0.2(3)
