#------------------------------------------------------------------------------
#$Date: 2022-09-21 18:44:46 +0300 (Wed, 21 Sep 2022) $
#$Revision: 278046 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/37/7223764.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_7223764
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 ad
_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             13-12-03
_audit_creation_method
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_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                   4.8953(4)
_cell_length_b                   13.2668(10)
_cell_length_c                   19.1081(14)
_cell_measurement_reflns_used    6750
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.1
_cell_volume                     1240.97(17)
_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      293.15
_diffrn_measured_fraction_theta_full 0.9846
_diffrn_measured_fraction_theta_max 0.9846
_diffrn_measurement_device_type  2013ncs0809_info
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.1106
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8061
_diffrn_reflns_theta_full        27.4783
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.5690
_exptl_crystal_description       needle
_exptl_crystal_F_000             600.4361
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.5264
_refine_diff_density_min         -0.4906
_refine_diff_density_rms         0.1215
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -1.5(12)
_refine_ls_d_res_high            0.7702
_refine_ls_d_res_low             9.5541
_refine_ls_goodness_of_fit_ref   1.0796
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    15
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0796
_refine_ls_R_factor_all          0.1606
_refine_ls_R_factor_gt           0.0700
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0709P)²+0.1768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1745
_reflns_Friedel_coverage         0.970
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              24
_reflns_limit_l_min              -24
_reflns_number_gt                1453
_reflns_number_total             2810
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ce01658d2.cif
_cod_data_source_block           2013ncs0809
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7223764
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 2.5(12) -1.5(12)
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:
 C9(H9), C10(H10), C11(H11), C12(H12), 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
O1 O 0.6476(16) 0.4374(4) 0.1514(2) 0.136(3) Uani 1.000000 .
O2 O 1.0014(12) 0.5238(7) 0.1583(3) 0.221(5) Uani 1.000000 .
O3 O 0.5369(11) 0.5975(3) 0.24574(19) 0.0896(16) Uani 1.000000 .
O4 O 0.5830(7) 0.4029(2) 0.49112(14) 0.0459(9) Uani 1.000000 .
O5 O 1.0146(6) 0.2929(2) 0.44363(12) 0.0379(8) Uani 1.000000 .
O6 O 1.0720(7) 0.3494(2) 0.59652(14) 0.0481(9) Uani 1.000000 .
H6a H 1.0268(7) 0.4116(2) 0.62079(14) 0.0721(14) Uiso 1.000000 R
H6b H 1.2532(7) 0.3648(2) 0.57849(14) 0.0721(14) Uiso 1.000000 R
N1 N 0.8521(12) 0.4695(5) 0.1832(2) 0.0712(16) Uani 1.000000 .
C1 C 0.8877(10) 0.4318(4) 0.2547(2) 0.0385(12) Uani 1.000000 .
C2 C 0.7334(9) 0.4646(3) 0.3103(2) 0.0330(11) Uani 1.000000 .
C3 C 0.5460(11) 0.5518(4) 0.3008(2) 0.0444(13) Uani 1.000000 .
C4 C 0.3771(9) 0.5830(3) 0.3609(2) 0.0369(11) Uani 1.000000 .
C5 C 0.3992(9) 0.5347(3) 0.4250(2) 0.0322(10) Uani 1.000000 .
C6 C 0.5876(9) 0.4471(3) 0.4340(2) 0.0337(11) Uani 1.000000 .
C7 C 0.9694(9) 0.3393(3) 0.3855(2) 0.0313(10) Uani 1.000000 .
C8 C 0.7676(9) 0.4176(3) 0.37649(19) 0.0289(10) Uani 1.000000 .
C9 C 1.1275(9) 0.3134(3) 0.3256(2) 0.0353(11) Uani 1.000000 .
H9 H 1.2631(9) 0.2647(3) 0.3298(2) 0.0423(13) Uiso 1.000000 R
C10 C 1.0863(10) 0.3580(4) 0.2621(2) 0.0400(12) Uani 1.000000 .
H10 H 1.1914(10) 0.3388(4) 0.2238(2) 0.0481(14) Uiso 1.000000 R
C11 C 0.2366(11) 0.5652(3) 0.4811(2) 0.0415(12) Uani 1.000000 .
H11 H 0.2498(11) 0.5320(3) 0.5239(2) 0.0498(14) Uiso 1.000000 R
C12 C 0.0560(11) 0.6444(4) 0.4734(2) 0.0492(13) Uani 1.000000 .
H12 H -0.0535(11) 0.6644(4) 0.5107(2) 0.0591(16) Uiso 1.000000 R
C13 C 0.0389(12) 0.6944(4) 0.4090(2) 0.0552(14) Uani 1.000000 .
H13 H -0.0792(12) 0.7488(4) 0.4038(2) 0.0662(17) Uiso 1.000000 R
C14 C 0.1948(10) 0.6636(4) 0.3538(2) 0.0480(13) Uani 1.000000 .
H14 H 0.1798(10) 0.6966(4) 0.3110(2) 0.0576(16) Uiso 1.000000 R
Li1 Li 0.8067(16) 0.3005(7) 0.5294(4) 0.044(2) 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 0.00300 0.00200 2.31000 1.02000 1.58900 0.86500 20.84400 10.20800 0.56900
51.65100 0.216 'Custom 4-Gaussian' custom
Li -0.00000 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 0.01100 0.00600 3.04900 2.28700 1.54600 0.86700 13.27700 5.70100 0.32400
32.90900 0.251 'Custom 4-Gaussian' custom
N 0.00600 0.00300 12.21300 3.13200 2.01300 1.16600 0.00600 9.89300 28.99800
0.58300 -11.529 'Custom 4-Gaussian' custom
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 O4 C6 132.1(4) . .
Li1 O5 C7 128.0(4) . .
Li1 O5 C7 130.8(3) 2_556 .
H6b O6 H6a 101.4 . .
Li1 O6 H6a 116.6 . .
Li1 O6 H6b 116.6 . .
O2 N1 O1 122.1(6) . .
C1 N1 O1 115.7(6) . .
C1 N1 O2 122.2(6) . .
C2 C1 N1 123.2(4) . .
C10 C1 N1 114.8(4) . .
C10 C1 C2 122.0(4) . .
C3 C2 C1 119.4(4) . .
C8 C2 C1 119.0(4) . .
C8 C2 C3 121.5(4) . .
C2 C3 O3 121.1(4) . .
C4 C3 O3 120.9(5) . .
C4 C3 C2 118.0(4) . .
C5 C4 C3 120.9(4) . .
C14 C4 C3 119.8(4) . .
C14 C4 C5 119.2(4) . .
C6 C5 C4 120.7(4) . .
C11 C5 C4 120.0(4) . .
C11 C5 C6 119.3(4) . .
C5 C6 O4 117.3(4) . .
C8 C6 O4 123.2(4) . .
C8 C6 C5 119.5(3) . .
C8 C7 O5 124.3(4) . .
C9 C7 O5 119.0(4) . .
C9 C7 C8 116.7(3) . .
C6 C8 C2 118.8(4) . .
C7 C8 C2 120.2(4) . .
C7 C8 C6 121.0(3) . .
H9 C9 C7 119.0(2) . .
C10 C9 C7 122.0(4) . .
C10 C9 H9 119.0(3) . .
C9 C10 C1 120.0(4) . .
H10 C10 C1 120.0(2) . .
H10 C10 C9 120.0(3) . .
H11 C11 C5 119.9(3) . .
C12 C11 C5 120.3(4) . .
C12 C11 H11 119.9(3) . .
H12 C12 C11 120.2(3) . .
C13 C12 C11 119.5(5) . .
C13 C12 H12 120.2(3) . .
H13 C13 C12 119.9(3) . .
C14 C13 C12 120.3(5) . .
C14 C13 H13 119.9(3) . .
C13 C14 C4 120.7(4) . .
H14 C14 C4 119.6(3) . .
H14 C14 C13 119.6(3) . .
O5 Li1 O4 90.8(3) . .
O5 Li1 O4 97.7(4) 2_456 .
O6 Li1 O4 113.8(5) . .
O6 Li1 O5 121.8(4) . 2_456
O6 Li1 O5 103.0(4) . .
Li1 Li1 O4 72.8(3) 2_456 .
Li1 Li1 O4 130.2(5) 2_556 .
Li1 Li1 O5 95.1(4) 2_456 .
Li1 Li1 O5 114.2(5) 2_556 2_456
Li1 Li1 O5 39.06(19) 2_456 2_456
Li1 Li1 O5 39.7(2) 2_556 .
Li1 Li1 O6 81.4(2) 2_556 .
Li1 Li1 O6 160.4(5) 2_456 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.246(7) .
O2 N1 1.132(7) .
O3 C3 1.216(5) .
O4 C6 1.239(4) .
O4 Li1 1.892(9) .
O5 C7 1.289(4) .
O5 Li1 1.933(8) .
O5 Li1 1.960(9) 2_556
O6 H6a 0.9722 .
O6 H6b 0.9733 .
O6 Li1 1.937(8) .
N1 C1 1.465(6) .
C1 C2 1.374(6) .
C1 C10 1.388(6) .
C2 C3 1.488(7) .
C2 C8 1.419(5) .
C3 C4 1.473(6) .
C4 C5 1.387(6) .
C4 C14 1.399(6) .
C5 C6 1.493(6) .
C5 C11 1.395(6) .
C6 C8 1.462(5) .
C7 C8 1.445(6) .
C7 C9 1.424(5) .
C9 H9 0.9300 .
C9 C10 1.364(6) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C11 C12 1.382(6) .
C12 H12 0.9300 .
C12 C13 1.400(6) .
C13 H13 0.9300 .
C13 C14 1.364(6) .
C14 H14 0.9300 .
Li1 Li1 3.008(10) 2_456
Li1 Li1 3.008(9) 2_556
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 2.5(12)
2 -1.5(12)
