# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Li2aqdc_120K(compound1)
_database_code_depnum_ccdc_archive 'CCDC 1419034'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        'Li2 anthraquinone-dicarboxylate'
_chemical_formula_moiety         'C16 H8 Li2 O7'
_chemical_formula_sum            'C16 H8 Li2 O7'
_chemical_formula_weight         326.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Li2 C16 H8 O7'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   18.9997(7)
_cell_length_b                   9.4546(3)
_cell_length_c                   7.4275(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.743(4)
_cell_angle_gamma                90.00
_cell_volume                     1327.55(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2420
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      30.4910
_cell_measurement_theta_min      4.2610
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.966
_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            'light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.1679
_exptl_crystal_size_min          0.0612
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8508
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         3.23
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9980
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0331436000
_diffrn_orient_matrix_UB_12      -0.0352355000
_diffrn_orient_matrix_UB_13      0.0079685000
_diffrn_orient_matrix_UB_21      -0.0161002000
_diffrn_orient_matrix_UB_22      -0.0602331000
_diffrn_orient_matrix_UB_23      -0.0434809000
_diffrn_orient_matrix_UB_31      0.0071216000
_diffrn_orient_matrix_UB_32      0.0274916000
_diffrn_orient_matrix_UB_33      -0.0851854000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2556
_reflns_number_total             3278
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_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  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.3540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1193
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
H2A H 0.0490(13) 0.856(3) -0.005(4) 0.044(7) Uiso 1 1 d . . .
H2B H 0.0292(15) 0.792(3) 0.160(4) 0.067(9) Uiso 1 1 d . . .
H9 H 0.2837 1.0611 0.4948 0.018 Uiso 1 1 calc R . .
H12 H 0.1448 1.4434 0.6282 0.016 Uiso 1 1 calc R . .
H20 H 0.3289 1.7746 0.4658 0.023 Uiso 1 1 calc R . .
H21 H 0.4605 1.3966 0.2797 0.026 Uiso 1 1 calc R . .
H22 H 0.4313 1.8146 0.3278 0.028 Uiso 1 1 calc R . .
H23 H 0.4969 1.6270 0.2348 0.029 Uiso 1 1 calc R . .
Li2 Li 0.15587(16) 0.7966(3) 0.2305(4) 0.0194(6) Uani 1 1 d . . .
Li3 Li -0.04700(15) 0.9992(3) 0.6538(4) 0.0185(6) Uani 1 1 d . . .
C8 C 0.28135(8) 1.27516(16) 0.5041(2) 0.0141(3) Uani 1 1 d . . .
C9 C 0.25566(8) 1.13779(16) 0.5201(2) 0.0148(3) Uani 1 1 d . . .
C10 C 0.16380(8) 0.96210(15) 0.5859(2) 0.0133(3) Uani 1 1 d . . .
C11 C 0.18833(8) 1.11446(15) 0.5738(2) 0.0126(3) Uani 1 1 d . . .
C12 C 0.17240(8) 1.36670(16) 0.6001(2) 0.0134(3) Uani 1 1 d . . .
C13 C 0.26737(8) 1.53688(16) 0.5452(2) 0.0141(3) Uani 1 1 d . . .
C14 C 0.14573(8) 1.23024(16) 0.6100(2) 0.0126(3) Uani 1 1 d . . .
C15 C 0.07021(8) 1.21019(15) 0.6521(2) 0.0128(3) Uani 1 1 d . . .
C16 C 0.35141(9) 1.29694(17) 0.4329(2) 0.0171(3) Uani 1 1 d . . .
C17 C 0.24003(8) 1.38979(15) 0.5484(2) 0.0129(3) Uani 1 1 d . . .
C18 C 0.33327(8) 1.56025(17) 0.4566(2) 0.0162(3) Uani 1 1 d . . .
C19 C 0.37306(8) 1.44627(17) 0.4028(2) 0.0167(3) Uani 1 1 d . . .
C20 C 0.35518(9) 1.69874(18) 0.4290(2) 0.0196(4) Uani 1 1 d . . .
C21 C 0.43430(9) 1.47202(19) 0.3179(2) 0.0219(4) Uani 1 1 d . . .
C22 C 0.41650(10) 1.72239(19) 0.3461(3) 0.0237(4) Uani 1 1 d . . .
C23 C 0.45595(9) 1.60997(19) 0.2904(3) 0.0245(4) Uani 1 1 d . . .
O1 O 0.13946(6) 0.90614(11) 0.43771(15) 0.0157(3) Uani 1 1 d . . .
O2 O 0.05908(6) 0.85317(12) 0.11677(17) 0.0173(3) Uani 1 1 d . . .
O3 O 0.23849(6) 1.63480(11) 0.61579(16) 0.0177(3) Uani 1 1 d . . .
O4 O 0.03977(6) 1.31107(11) 0.72613(16) 0.0156(3) Uani 1 1 d . . .
O5 O 0.04114(6) 1.09447(11) 0.60681(15) 0.0151(3) Uani 1 1 d . . .
O6 O 0.38843(7) 1.19677(13) 0.39805(19) 0.0263(3) Uani 1 1 d . . .
O7 O 0.17184(6) 0.90400(11) 0.73646(16) 0.0189(3) 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
Li2 Li3 3.017(4) 3_576 ?
Li2 C10 2.682(3) 4_575 ?
Li2 O3 1.969(3) 4_585 ?
Li2 O7 1.921(3) 4_575 ?
Li3 Li2 3.017(4) 3_576 ?
Li3 Li3 3.037(6) 3_576 ?
Li3 C10 2.727(3) 3_576 ?
Li3 O1 2.027(3) 3_576 ?
Li3 O2 2.232(3) 3_576 ?
Li3 O4 1.988(3) 2_546 ?
Li3 O5 2.142(3) 3_576 ?
C8 C9 1.397(2) . ?
C8 C16 1.495(2) . ?
C8 C17 1.397(2) . ?
C9 C11 1.395(2) . ?
C10 Li2 2.682(3) 4_576 ?
C10 Li3 2.727(3) 3_576 ?
C10 C11 1.520(2) . ?
C11 C14 1.403(2) . ?
C12 C14 1.391(2) . ?
C12 C17 1.395(2) . ?
C13 C17 1.486(2) . ?
C13 C18 1.488(2) . ?
C14 C15 1.511(2) . ?
C16 C19 1.494(2) . ?
C18 C19 1.397(2) . ?
C18 C20 1.395(2) . ?
C19 C21 1.399(2) . ?
C20 C22 1.389(2) . ?
C21 C23 1.389(2) . ?
C22 C23 1.387(3) . ?
O1 Li2 1.906(3) . ?
O1 Li3 2.027(3) 3_576 ?
O1 C10 1.2664(19) . ?
O2 Li2 2.018(3) . ?
O2 Li3 2.232(3) 3_576 ?
O3 Li2 1.969(3) 4_586 ?
O3 C13 1.2210(19) . ?
O4 Li3 1.988(3) 2_556 ?
O4 C15 1.2689(18) . ?
O5 Li3 2.142(3) 3_576 ?
O5 Li3 1.963(3) . ?
O5 C15 1.2562(18) . ?
O6 C16 1.2229(19) . ?
O7 Li2 1.921(3) 4_576 ?
O7 C10 1.2414(19) . ?

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
C10 Li2 Li3 139.94(13) 4_575 3_576 ?
O1 Li2 Li3 41.42(9) . 3_576 ?
O1 Li2 C10 147.04(15) . 4_575 ?
O1 Li2 O2 88.75(12) . . ?
O1 Li2 O3 111.85(15) . 4_585 ?
O1 Li2 O7 123.79(16) . 4_575 ?
O2 Li2 Li3 47.73(9) . 3_576 ?
O2 Li2 C10 99.17(12) . 4_575 ?
O3 Li2 Li3 120.76(13) 4_585 3_576 ?
O3 Li2 C10 92.75(11) 4_585 4_575 ?
O3 Li2 O2 117.66(15) 4_585 . ?
O7 Li2 Li3 137.45(14) 4_575 3_576 ?
O7 Li2 C10 24.96(6) 4_575 4_575 ?
O7 Li2 O2 113.99(15) 4_575 . ?
O7 Li2 O3 101.78(14) 4_575 4_585 ?
Li2 Li3 Li3 133.04(15) 3_576 3_576 ?
C10 Li3 Li2 64.14(9) 3_576 3_576 ?
C10 Li3 Li3 90.55(13) 3_576 3_576 ?
O1 Li3 Li2 38.47(8) 3_576 3_576 ?
O1 Li3 Li3 107.49(16) 3_576 3_576 ?
O1 Li3 C10 25.94(6) 3_576 3_576 ?
O1 Li3 O2 80.10(11) 3_576 3_576 ?
O1 Li3 O5 90.07(12) 3_576 3_576 ?
O2 Li3 Li2 41.98(8) 3_576 3_576 ?
O2 Li3 Li3 133.16(17) 3_576 3_576 ?
O2 Li3 C10 105.99(11) 3_576 3_576 ?
O4 Li3 Li2 117.60(13) 2_546 3_576 ?
O4 Li3 Li3 108.81(15) 2_546 3_576 ?
O4 Li3 C10 115.35(13) 2_546 3_576 ?
O4 Li3 O1 124.34(15) 2_546 3_576 ?
O4 Li3 O2 102.99(13) 2_546 3_576 ?
O4 Li3 O5 91.61(12) 2_546 3_576 ?
O5 Li3 Li2 128.41(13) 3_576 3_576 ?
O5 Li3 Li2 112.23(13) . 3_576 ?
O5 Li3 Li3 40.06(8) 3_576 3_576 ?
O5 Li3 Li3 44.58(8) . 3_576 ?
O5 Li3 C10 118.37(13) . 3_576 ?
O5 Li3 C10 65.03(9) 3_576 3_576 ?
O5 Li3 O1 117.63(14) . 3_576 ?
O5 Li3 O2 90.19(12) . 3_576 ?
O5 Li3 O2 165.27(15) 3_576 3_576 ?
O5 Li3 O4 117.92(14) . 2_546 ?
O5 Li3 O5 84.64(11) . 3_576 ?
C9 C8 C16 119.29(14) . . ?
C9 C8 C17 119.48(14) . . ?
C17 C8 C16 121.18(14) . . ?
C11 C9 C8 120.63(14) . . ?
Li2 C10 Li3 108.01(10) 4_576 3_576 ?
C11 C10 Li2 156.68(13) . 4_576 ?
C11 C10 Li3 93.92(11) . 3_576 ?
O1 C10 Li2 86.38(11) . 4_576 ?
O1 C10 Li3 44.44(9) . 3_576 ?
O1 C10 C11 115.59(13) . . ?
O7 C10 Li2 40.75(9) . 4_576 ?
O7 C10 Li3 131.77(12) . 3_576 ?
O7 C10 C11 117.53(14) . . ?
O7 C10 O1 126.83(14) . . ?
C9 C11 C10 117.54(13) . . ?
C9 C11 C14 119.63(13) . . ?
C14 C11 C10 122.81(14) . . ?
C14 C12 C17 120.69(14) . . ?
C17 C13 C18 117.20(14) . . ?
O3 C13 C17 122.01(14) . . ?
O3 C13 C18 120.77(14) . . ?
C11 C14 C15 121.32(13) . . ?
C12 C14 C11 119.56(14) . . ?
C12 C14 C15 119.08(14) . . ?
O4 C15 C14 118.61(13) . . ?
O5 C15 C14 117.07(13) . . ?
O5 C15 O4 124.29(14) . . ?
C19 C16 C8 116.84(14) . . ?
O6 C16 C8 121.31(14) . . ?
O6 C16 C19 121.83(14) . . ?
C8 C17 C13 121.13(14) . . ?
C12 C17 C8 119.90(14) . . ?
C12 C17 C13 118.96(14) . . ?
C19 C18 C13 121.00(14) . . ?
C20 C18 C13 118.74(15) . . ?
C20 C18 C19 120.26(15) . . ?
C18 C19 C16 121.41(14) . . ?
C18 C19 C21 119.52(15) . . ?
C21 C19 C16 119.07(15) . . ?
C22 C20 C18 119.46(16) . . ?
C23 C21 C19 120.09(16) . . ?
C23 C22 C20 120.73(16) . . ?
C22 C23 C21 119.93(16) . . ?
Li2 O1 Li3 100.10(13) . 3_576 ?
C10 O1 Li2 148.62(14) . . ?
C10 O1 Li3 109.62(12) . 3_576 ?
Li2 O2 Li3 90.29(12) . 3_576 ?
C13 O3 Li2 147.94(13) . 4_586 ?
C15 O4 Li3 148.51(13) . 2_556 ?
Li3 O5 Li3 95.36(11) . 3_576 ?
C15 O5 Li3 122.74(12) . 3_576 ?
C15 O5 Li3 135.40(13) . . ?
C10 O7 Li2 114.29(13) . 4_576 ?

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
-26 2 0 0.0602 -26.0018 1.9789 0.0301 -0.9313 0.2981 -0.1333
26 -2 0 0.0010 26.0018 -1.9789 -0.0301 0.9313 -0.2981 0.1333
3 -13 0 0.0938 3.0216 -12.9295 -0.0018 0.5557 0.7302 -0.3338
-3 13 0 0.0518 -3.0216 12.9295 0.0018 -0.5557 -0.7302 0.3338
-9 8 8 0.1634 -8.9996 7.9467 7.9605 -0.5149 -0.6799 -0.5237
9 -8 -8 0.2384 8.9996 -7.9467 -7.9605 0.5149 0.6799 0.5237
6 7 -9 0.2639 5.9730 6.9731 -8.9529 -0.1191 -0.1269 0.9969
-6 -7 9 0.2639 -5.9730 -6.9731 8.9529 0.1191 0.1269 -0.9969

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Li2aqdc_RT
_database_code_depnum_ccdc_archive 'CCDC 1419035'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        'Lithium anthraquinone dicarboxylate'
_chemical_formula_moiety         'C16 H8 Li2 O7'
_chemical_formula_sum            'C16 H8 Li2 O7'
_chemical_formula_weight         326.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Li2 C16 O7 H8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0010 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   19.0868(8)
_cell_length_b                   9.4849(4)
_cell_length_c                   7.4588(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.757(4)
_cell_angle_gamma                90.00
_cell_volume                     1345.66(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2411
_cell_measurement_temperature    302.3(6)
_cell_measurement_theta_max      67.2730
_cell_measurement_theta_min      2.3090
_exptl_absorpt_coefficient_mu    1.065
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.729
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.4527
_exptl_crystal_size_mid          0.2122
_exptl_crystal_size_min          0.0508
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4826
_diffrn_reflns_theta_full        67.40
_diffrn_reflns_theta_max         67.40
_diffrn_reflns_theta_min         2.32
_diffrn_ambient_temperature      302.3(6)
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   37.00   96.00   1.0000    1.7000
omega____ theta____ kappa____ phi______ frames
    -       25.9162   57.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega   42.00   69.00   1.0000    1.7000
omega____ theta____ kappa____ phi______ frames
    -       25.9162 -178.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00  119.00   1.0000    1.7000
omega____ theta____ kappa____ phi______ frames
    -       25.9162  178.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
  4 omega   -8.00   36.00   1.0000    1.7000
omega____ theta____ kappa____ phi______ frames
    -       25.9162   57.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega -136.00 -109.00   1.0000    6.8000
omega____ theta____ kappa____ phi______ frames
    -      -67.7081 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega -145.00   10.00   1.0000    6.8000
omega____ theta____ kappa____ phi______ frames
    -      -67.7081  -15.0000  -60.0000 155

#__ type_ start__ end____ width___ exp.time_
  7 omega -134.00 -104.00   1.0000    6.8000
omega____ theta____ kappa____ phi______ frames
    -      -67.7081 -111.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega -145.00 -117.00   1.0000    6.8000
omega____ theta____ kappa____ phi______ frames
    -      -67.7081 -111.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  9 omega -150.00 -118.00   1.0000    6.8000
omega____ theta____ kappa____ phi______ frames
    -      -67.7081 -111.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 10 omega -142.00 -106.00   1.0000    6.8000
omega____ theta____ kappa____ phi______ frames
    -      -67.7081 -111.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
 11 omega -150.00 -113.00   1.0000    6.8000
omega____ theta____ kappa____ phi______ frames
    -      -67.7081 -114.0000 -135.0000 37

#__ type_ start__ end____ width___ exp.time_
 12 omega -143.00 -101.00   1.0000    6.8000
omega____ theta____ kappa____ phi______ frames
    -      -67.7081  -94.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
 13 omega  -14.00   16.00   1.0000    6.8000
omega____ theta____ kappa____ phi______ frames
    -       67.7081  -30.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
 14 omega   44.00   69.00   1.0000    6.8000
omega____ theta____ kappa____ phi______ frames
    -       67.7081  -30.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   50.00   86.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega  133.00  173.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -32.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 17 omega   30.00   75.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -43.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 18 omega   35.00   69.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -65.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
 19 omega   83.00  117.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 20 omega   37.00   64.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -43.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega  146.00  173.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   92.00  123.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 23 omega   25.00   85.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
 24 omega  134.00  162.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -32.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 25 omega   30.00   72.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -43.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
 26 omega   40.00   67.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -43.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 27 omega   96.00  126.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -65.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 28 omega   67.00  109.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  138.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
 29 omega  123.00  157.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  104.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 30 omega   79.00  116.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  104.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 31 omega  106.00  153.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 32 omega  133.00  175.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -32.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
 33 omega  135.00  173.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -32.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
 34 omega   50.00   77.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000  -60.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0002757000
_diffrn_orient_matrix_UB_12      -0.1434751000
_diffrn_orient_matrix_UB_13      0.0971515000
_diffrn_orient_matrix_UB_21      0.0798528000
_diffrn_orient_matrix_UB_22      -0.0119345000
_diffrn_orient_matrix_UB_23      -0.0130470000
_diffrn_orient_matrix_UB_31      0.0131862000
_diffrn_orient_matrix_UB_32      0.0752779000
_diffrn_orient_matrix_UB_33      0.1827274000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2167
_reflns_number_total             2407
_reflns_odcompleteness_completeness 93.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_threshold_expression     >2sigma(I)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.2674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.11342(6) 0.69390(13) 0.6097(2) 0.0556(4) Uani 1 d . . .
O2 O 0.26239(5) 1.12992(10) 0.38858(15) 0.0362(3) Uani 1 d . . .
O3 O 0.43974(5) 1.14419(11) 0.38884(14) 0.0366(3) Uani 1 d . . .
H3A H 0.4450 1.1350 0.5120 0.055 Uiso 1 d . . R
H3B H 0.4747 1.2060 0.3520 0.055 Uiso 1 d . . R
O4 O 0.45919(5) 0.59376(10) 0.39054(13) 0.0296(2) Uani 1 d . . .
O5 O 0.45933(5) 0.80797(10) 0.26953(13) 0.0312(2) Uani 1 d . . .
O6 O 0.36171(5) 0.40571(10) 0.56456(13) 0.0308(2) Uani 1 d . . .
O7 O 0.32905(6) 0.40168(11) 0.27082(14) 0.0393(3) Uani 1 d . . .
C1 C 0.14991(7) 0.79340(16) 0.5723(2) 0.0343(3) Uani 1 d . . .
C2 C 0.21981(7) 0.77129(15) 0.50122(17) 0.0275(3) Uani 1 d . . .
C3 C 0.26093(7) 0.88630(14) 0.45521(17) 0.0255(3) Uani 1 d . . .
C4 C 0.23341(7) 1.03213(14) 0.45912(17) 0.0277(3) Uani 1 d . . .
C5 C 0.16744(7) 1.05541(16) 0.54702(18) 0.0317(3) Uani 1 d . . .
C6 C 0.12764(7) 0.94156(17) 0.6016(2) 0.0344(3) Uani 1 d . . .
C7 C 0.06629(8) 0.9674(2) 0.6852(2) 0.0474(4) Uani 1 d . . .
H7 H 0.0398 0.8923 0.7227 0.057 Uiso 1 calc . . R
C8 C 0.04457(9) 1.1046(2) 0.7127(3) 0.0546(5) Uani 1 d . . .
H8 H 0.0036 1.1215 0.7684 0.065 Uiso 1 calc . . R
C9 C 0.08389(9) 1.2164(2) 0.6572(3) 0.0523(4) Uani 1 d . . .
H9 H 0.0690 1.3083 0.6752 0.063 Uiso 1 calc . . R
C10 C 0.14519(8) 1.19287(18) 0.5752(2) 0.0425(4) Uani 1 d . . .
H10 H 0.1715 1.2687 0.5390 0.051 Uiso 1 calc . . R
C11 C 0.32779(7) 0.86284(13) 0.40175(17) 0.0255(3) Uani 1 d . . .
H11 H 0.3551 0.9393 0.3724 0.031 Uiso 1 calc . . R
C12 C 0.35484(6) 0.72748(13) 0.39105(16) 0.0236(3) Uani 1 d . . .
C13 C 0.42992(6) 0.70831(13) 0.34549(16) 0.0238(3) Uani 1 d . . .
C14 C 0.31269(7) 0.61224(14) 0.43001(16) 0.0247(3) Uani 1 d . . .
C15 C 0.33716(7) 0.46043(13) 0.41849(17) 0.0260(3) Uani 1 d . . .
C16 C 0.24565(7) 0.63508(14) 0.48448(18) 0.0285(3) Uani 1 d . . .
H16 H 0.2178 0.5584 0.5100 0.034 Uiso 1 calc . . R
Li1 Li 0.34443(13) 1.2018(2) 0.2733(3) 0.0339(5) Uani 1 d . . .
Li2 Li 0.54656(12) 0.4964(3) 0.3462(3) 0.0325(5) Uani 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 C1 1.2188(19) . ?
O2 C4 1.2212(17) . ?
O3 H3A 0.9198 . ?
O3 H3B 0.9456 . ?
O4 C13 1.2547(16) . ?
O5 C13 1.2579(16) . ?
O6 C15 1.2615(16) . ?
O7 C15 1.2326(17) . ?
C1 C2 1.4907(18) . ?
C1 C6 1.490(2) . ?
C2 C3 1.4030(19) . ?
C2 C16 1.3922(19) . ?
C3 C4 1.4807(18) . ?
C3 C11 1.3862(18) . ?
C4 C5 1.4834(18) . ?
C5 C6 1.400(2) . ?
C5 C10 1.393(2) . ?
C6 C7 1.393(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.3886(18) . ?
C12 C13 1.5110(17) . ?
C12 C14 1.4018(18) . ?
C14 C15 1.5184(18) . ?
C14 C16 1.3913(19) . ?
C16 H16 0.9300 . ?

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
H3A O3 H3B 109.2 . . ?
O1 C1 C2 121.18(14) . . ?
O1 C1 C6 121.43(13) . . ?
C6 C1 C2 117.36(12) . . ?
C3 C2 C1 120.86(12) . . ?
C16 C2 C1 119.77(12) . . ?
C16 C2 C3 119.34(12) . . ?
C2 C3 C4 120.99(11) . . ?
C11 C3 C2 119.51(12) . . ?
C11 C3 C4 119.49(12) . . ?
O2 C4 C3 121.79(12) . . ?
O2 C4 C5 120.58(12) . . ?
C3 C4 C5 117.59(12) . . ?
C6 C5 C4 120.98(13) . . ?
C10 C5 C4 119.13(14) . . ?
C10 C5 C6 119.89(13) . . ?
C5 C6 C1 121.10(12) . . ?
C7 C6 C1 119.50(14) . . ?
C7 C6 C5 119.40(15) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.27(17) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.97(15) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.62(16) . . ?
C10 C9 H9 119.7 . . ?
C5 C10 H10 120.1 . . ?
C9 C10 C5 119.85(16) . . ?
C9 C10 H10 120.1 . . ?
C3 C11 H11 119.3 . . ?
C3 C11 C12 121.37(12) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 119.23(11) . . ?
C11 C12 C14 119.11(11) . . ?
C14 C12 C13 121.61(11) . . ?
O4 C13 O5 124.47(11) . . ?
O4 C13 C12 116.97(11) . . ?
O5 C13 C12 118.55(11) . . ?
C12 C14 C15 122.90(11) . . ?
C16 C14 C12 119.78(12) . . ?
C16 C14 C15 117.31(11) . . ?
O6 C15 C14 115.80(11) . . ?
O7 C15 O6 126.58(12) . . ?
O7 C15 C14 117.57(11) . . ?
C2 C16 H16 119.6 . . ?
C14 C16 C2 120.79(12) . . ?
C14 C16 H16 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.75(14) . . . . ?
O1 C1 C2 C16 -3.0(2) . . . . ?
O1 C1 C6 C5 -175.55(15) . . . . ?
O1 C1 C6 C7 4.6(2) . . . . ?
O2 C4 C5 C6 169.31(13) . . . . ?
O2 C4 C5 C10 -10.7(2) . . . . ?
C1 C2 C3 C4 -5.95(19) . . . . ?
C1 C2 C3 C11 175.38(12) . . . . ?
C1 C2 C16 C14 -175.64(12) . . . . ?
C1 C6 C7 C8 -179.64(16) . . . . ?
C2 C1 C6 C5 6.5(2) . . . . ?
C2 C1 C6 C7 -173.36(14) . . . . ?
C2 C3 C4 O2 -166.07(13) . . . . ?
C2 C3 C4 C5 11.90(18) . . . . ?
C2 C3 C11 C12 0.61(19) . . . . ?
C3 C2 C16 C14 2.7(2) . . . . ?
C3 C4 C5 C6 -8.68(19) . . . . ?
C3 C4 C5 C10 171.26(13) . . . . ?
C3 C11 C12 C13 -175.47(11) . . . . ?
C3 C11 C12 C14 1.95(19) . . . . ?
C4 C3 C11 C12 -178.08(11) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 C7 179.44(14) . . . . ?
C4 C5 C10 C9 -179.91(15) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C6 C1 C2 C3 -3.27(19) . . . . ?
C6 C1 C2 C16 175.02(12) . . . . ?
C6 C5 C10 C9 0.0(2) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
C10 C5 C6 C1 179.66(14) . . . . ?
C10 C5 C6 C7 -0.5(2) . . . . ?
C11 C3 C4 O2 12.60(19) . . . . ?
C11 C3 C4 C5 -169.43(12) . . . . ?
C11 C12 C13 O4 158.41(12) . . . . ?
C11 C12 C13 O5 -20.01(17) . . . . ?
C11 C12 C14 C15 178.79(11) . . . . ?
C11 C12 C14 C16 -2.19(18) . . . . ?
C12 C14 C15 O6 96.45(15) . . . . ?
C12 C14 C15 O7 -85.96(16) . . . . ?
C12 C14 C16 C2 -0.12(19) . . . . ?
C13 C12 C14 C15 -3.85(18) . . . . ?
C13 C12 C14 C16 175.17(11) . . . . ?
C14 C12 C13 O4 -18.94(17) . . . . ?
C14 C12 C13 O5 162.64(12) . . . . ?
C15 C14 C16 C2 178.95(11) . . . . ?
C16 C2 C3 C4 175.75(12) . . . . ?
C16 C2 C3 C11 -2.91(19) . . . . ?
C16 C14 C15 O6 -82.59(14) . . . . ?
C16 C14 C15 O7 94.99(15) . . . . ?

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
-2 6 0 0.1005 -1.9972 6.0049 0.0015 -0.8620 -0.2312 0.4260
2 -6 0 0.1005 1.9972 -6.0049 -0.0015 0.8620 0.2312 -0.4260
-2 0 -5 0.2561 -1.9948 0.0007 -4.9976 -0.4862 -0.0941 -0.9395
2 0 5 0.1721 1.9948 -0.0007 4.9976 0.4862 0.0941 0.9395
-12 0 0 0.0498 -11.9996 0.0005 -0.0023 -0.0036 -0.9582 -0.1586
12 0 0 0.0010 11.9996 -0.0005 0.0023 0.0036 0.9582 0.1586

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_description       block
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_Li-H-aqdc_120K
_database_code_depnum_ccdc_archive 'CCDC 1419036'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        'Lithium anthraquinonedicarboxylate'
_chemical_formula_moiety         'C16 H7 Li O6'
_chemical_formula_sum            'C16 H7 Li O6'
_chemical_formula_weight         302.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Li1 C16 O6 H7'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0010 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.0799(2)
_cell_length_b                   10.6463(2)
_cell_length_c                   14.6639(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.507(2)
_cell_angle_gamma                90.00
_cell_volume                     1231.47(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14169
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0063
_cell_measurement_theta_min      3.0869
_exptl_absorpt_coefficient_mu    1.063
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_correction_T_min  0.855
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.2714
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.1942
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29952
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.00
_diffrn_reflns_theta_min         5.18
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -33.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   95.0000  -13.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -23.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega -116.00  -30.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -77.0000  -90.0000 86

#__ type_ start__ end____ width___ exp.time_
  5 omega  -68.00   -7.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -54.7500   57.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
  6 omega   73.00   99.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -       54.7500  125.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   81.00  127.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -       54.7500   95.0000  166.0000 46

#__ type_ start__ end____ width___ exp.time_
  8 omega   74.00  116.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -       54.7500  125.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega -147.00 -105.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -75.0000 -111.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
 10 omega   44.00   88.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  150.0000 44

#__ type_ start__ end____ width___ exp.time_
 11 omega   53.00   96.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  178.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
 12 omega   58.00   86.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   80.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 14 omega   46.00   74.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -63.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00   82.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00   72.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 17 omega   86.00  144.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 18 omega   46.00   71.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   36.00   72.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 20 omega   37.00   69.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 21 omega   37.00   62.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   54.00   80.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   44.00   84.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -63.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
 24 omega   97.00  123.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -63.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   45.00   91.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -63.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
 26 omega   38.00   64.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega   98.00  124.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   37.00   62.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega   46.00   71.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 30 omega   86.00  112.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -63.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   35.00   72.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  150.0000 37

#__ type_ start__ end____ width___ exp.time_
 32 omega  110.00  135.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -70.0000 -103.4428 25

#__ type_ start__ end____ width___ exp.time_
 33 omega   63.00   88.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 34 omega  -25.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
 35 omega  -22.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 91

#__ type_ start__ end____ width___ exp.time_
 36 omega -126.00  -23.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -77.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
 37 omega -113.00  -18.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  125.0000 -150.0000 95

#__ type_ start__ end____ width___ exp.time_
 38 omega -126.00  -23.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -77.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 39 omega   33.00  124.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -       54.7500   57.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
 40 omega   33.00  124.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -       54.7500   57.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
 41 omega  -14.00   76.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -       54.7500  -57.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 42 omega -146.00  -43.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
 43 omega -146.00  -43.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000    0.0000 103

#__ type_ start__ end____ width___ exp.time_
 44 omega -146.00  -43.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000  -60.0000 103

#__ type_ start__ end____ width___ exp.time_
 45 omega -146.00  -43.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000 -120.0000 103

#__ type_ start__ end____ width___ exp.time_
 46 omega -146.00  -43.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
 47 omega   85.00  177.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   63.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
 48 omega   36.00   90.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
 49 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -150.0000 100

#__ type_ start__ end____ width___ exp.time_
 50 omega   36.00   90.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
 51 omega   70.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   25.0000  -60.0000 108

#__ type_ start__ end____ width___ exp.time_
 52 omega   35.00   72.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 53 omega   37.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   12.0000  150.0000 141

#__ type_ start__ end____ width___ exp.time_
 54 omega   36.00   90.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000   90.0000 54

#__ type_ start__ end____ width___ exp.time_
 55 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   60.0000 100

#__ type_ start__ end____ width___ exp.time_
 56 omega   82.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   37.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
 57 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
 58 omega  -20.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -105.0000  157.0000 67

#__ type_ start__ end____ width___ exp.time_
 59 omega  -69.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -150.0000 91

#__ type_ start__ end____ width___ exp.time_
 60 omega -126.00  -23.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 61 omega -126.00  -23.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -77.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
 62 omega -126.00  -23.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -77.0000  -60.0000 103

#__ type_ start__ end____ width___ exp.time_
 63 omega  -96.00    8.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -54.7500   95.0000  166.0000 104

#__ type_ start__ end____ width___ exp.time_
 64 omega   23.00  126.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000   90.0000 103

#__ type_ start__ end____ width___ exp.time_
 65 omega   23.00  126.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 66 omega -146.00  -43.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
 67 omega -146.00  -42.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -79.0000  177.7498 104

#__ type_ start__ end____ width___ exp.time_
 68 omega -146.00  -43.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 69 omega -146.00  -43.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 70 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
 71 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 72 omega   37.00  149.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
 73 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
 74 omega   37.00  149.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000  150.0000 112

#__ type_ start__ end____ width___ exp.time_
 75 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  150.0000 100

#__ type_ start__ end____ width___ exp.time_
 76 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 77 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 78 omega   37.00  149.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000 -150.0000 112

#__ type_ start__ end____ width___ exp.time_
 79 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
 80 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
 81 omega   78.00  178.00   1.0000    2.2800
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
 82 omega  -69.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000    0.0000 83
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1088223000
_diffrn_orient_matrix_UB_12      -0.0490349000
_diffrn_orient_matrix_UB_13      -0.0926405000
_diffrn_orient_matrix_UB_21      0.0228125000
_diffrn_orient_matrix_UB_22      0.1262135000
_diffrn_orient_matrix_UB_23      -0.0472132000
_diffrn_orient_matrix_UB_31      0.1604715000
_diffrn_orient_matrix_UB_32      -0.0510455000
_diffrn_orient_matrix_UB_33      -0.0278269000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2170
_reflns_number_total             2333
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_threshold_expression     >2sigma(I)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0609P)²+0.2365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0938
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.88526(11) -0.05861(8) 0.35367(6) 0.0249(2) Uani 1 d . . .
O2 O 0.70249(10) 0.25934(7) 0.60013(6) 0.0218(2) Uani 1 d . . .
O3 O 0.49968(11) -0.08494(7) 0.75718(5) 0.0226(2) Uani 1 d . . .
O4 O 0.58223(12) -0.28024(7) 0.74960(6) 0.0264(2) Uani 1 d . . .
H4 H 0.6300 -0.3434 0.7055 0.040 Uiso 1 d . . R
O5 O 0.66236(11) -0.41733(7) 0.63200(5) 0.0216(2) Uani 1 d . . .
O6 O 0.61841(11) -0.39978(7) 0.47795(5) 0.0225(2) Uani 1 d . . .
C1 C 0.83388(13) 0.01450(10) 0.40519(7) 0.0182(2) Uani 1 d . . .
C2 C 0.75875(13) -0.03225(10) 0.48322(7) 0.0169(2) Uani 1 d . . .
C3 C 0.71914(13) 0.04908(10) 0.55039(7) 0.0169(2) Uani 1 d . . .
C4 C 0.74205(13) 0.18757(10) 0.54292(7) 0.0178(2) Uani 1 d . . .
C5 C 0.80936(14) 0.23471(10) 0.46276(8) 0.0192(2) Uani 1 d . . .
C6 C 0.84948(14) 0.15257(10) 0.39561(7) 0.0193(2) Uani 1 d . . .
C7 C 0.90853(15) 0.20062(11) 0.32040(8) 0.0226(3) Uani 1 d . . .
H7 H 0.9347 0.1463 0.2759 0.027 Uiso 1 calc . . R
C8 C 0.92856(15) 0.32911(12) 0.31142(8) 0.0267(3) Uani 1 d . . .
H8 H 0.9677 0.3609 0.2609 0.032 Uiso 1 calc . . R
C9 C 0.89004(17) 0.41006(11) 0.37796(9) 0.0284(3) Uani 1 d . . .
H9 H 0.9039 0.4962 0.3719 0.034 Uiso 1 calc . . R
C10 C 0.83105(16) 0.36372(11) 0.45340(8) 0.0253(3) Uani 1 d . . .
H10 H 0.8059 0.4187 0.4978 0.030 Uiso 1 calc . . R
C11 C 0.65528(13) 0.00000(10) 0.62355(7) 0.0174(2) Uani 1 d . . .
H11 H 0.6267 0.0543 0.6674 0.021 Uiso 1 calc . . R
C12 C 0.63297(13) -0.12970(10) 0.63273(7) 0.0170(2) Uani 1 d . . .
C13 C 0.56566(14) -0.16607(10) 0.71793(7) 0.0183(2) Uani 1 d . . .
C14 C 0.64625(14) -0.35299(10) 0.55707(7) 0.0183(2) Uani 1 d . . .
C15 C 0.66908(13) -0.21131(10) 0.56338(7) 0.0169(2) Uani 1 d . . .
C16 C 0.73015(13) -0.16002(10) 0.48957(7) 0.0177(2) Uani 1 d . . .
H16 H 0.7523 -0.2131 0.4433 0.021 Uiso 1 calc . . R
Li1 Li 0.4307(3) -0.41079(17) 0.37411(13) 0.0228(4) Uani 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 C1 1.2185(13) . ?
O2 C4 1.2272(14) . ?
O3 C13 1.2224(14) . ?
O4 H4 1.0619 . ?
O4 C13 1.2977(14) . ?
O5 H4 1.4042 . ?
O5 C14 1.2773(13) . ?
O6 C14 1.2377(13) . ?
C1 C2 1.4921(15) . ?
C1 C6 1.4846(15) . ?
C2 C3 1.3996(15) . ?
C2 C16 1.3863(15) . ?
C3 C4 1.4929(15) . ?
C3 C11 1.3893(15) . ?
C4 C5 1.4854(15) . ?
C5 C6 1.4063(16) . ?
C5 C10 1.3951(16) . ?
C6 C7 1.3905(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.3871(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.3868(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.3867(17) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.4028(15) . ?
C12 C13 1.5170(15) . ?
C12 C15 1.4151(15) . ?
C14 C15 1.5200(14) . ?
C15 C16 1.3944(15) . ?
C16 H16 0.9300 . ?

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
C13 O4 H4 113.5 . . ?
C14 O5 H4 111.0 . . ?
O1 C1 C2 120.81(10) . . ?
O1 C1 C6 121.77(10) . . ?
C6 C1 C2 117.37(9) . . ?
C3 C2 C1 121.76(10) . . ?
C16 C2 C1 118.70(10) . . ?
C16 C2 C3 119.53(10) . . ?
C2 C3 C4 120.56(10) . . ?
C11 C3 C2 119.38(10) . . ?
C11 C3 C4 120.05(10) . . ?
O2 C4 C3 120.66(10) . . ?
O2 C4 C5 121.65(10) . . ?
C5 C4 C3 117.66(10) . . ?
C6 C5 C4 121.56(10) . . ?
C10 C5 C4 119.07(10) . . ?
C10 C5 C6 119.37(10) . . ?
C5 C6 C1 120.82(10) . . ?
C7 C6 C1 119.34(10) . . ?
C7 C6 C5 119.82(10) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.35(11) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.83(11) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.56(11) . . ?
C10 C9 H9 119.7 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.06(11) . . ?
C9 C10 H10 120.0 . . ?
C3 C11 H11 119.3 . . ?
C3 C11 C12 121.41(10) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 113.99(9) . . ?
C11 C12 C15 118.99(10) . . ?
C15 C12 C13 126.99(10) . . ?
O3 C13 O4 121.00(10) . . ?
O3 C13 C12 118.56(9) . . ?
O4 C13 C12 120.41(10) . . ?
O5 C14 C15 119.43(9) . . ?
O6 C14 O5 123.67(10) . . ?
O6 C14 C15 116.85(9) . . ?
C12 C15 C14 127.73(10) . . ?
C16 C15 C12 118.68(10) . . ?
C16 C15 C14 113.58(9) . . ?
C2 C16 C15 121.91(10) . . ?
C2 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 171.61(10) . . . . ?
O1 C1 C2 C16 -7.44(16) . . . . ?
O1 C1 C6 C5 -171.85(10) . . . . ?
O1 C1 C6 C7 6.57(16) . . . . ?
O2 C4 C5 C6 -177.92(10) . . . . ?
O2 C4 C5 C10 1.23(16) . . . . ?
O5 C14 C15 C12 -30.91(16) . . . . ?
O5 C14 C15 C16 150.38(10) . . . . ?
O6 C14 C15 C12 151.55(11) . . . . ?
O6 C14 C15 C16 -27.15(14) . . . . ?
C1 C2 C3 C4 3.49(15) . . . . ?
C1 C2 C3 C11 -177.61(9) . . . . ?
C1 C2 C16 C15 176.41(10) . . . . ?
C1 C6 C7 C8 -178.23(10) . . . . ?
C2 C1 C6 C5 5.72(15) . . . . ?
C2 C1 C6 C7 -175.87(9) . . . . ?
C2 C3 C4 O2 177.74(10) . . . . ?
C2 C3 C4 C5 -0.57(15) . . . . ?
C2 C3 C11 C12 1.38(16) . . . . ?
C3 C2 C16 C15 -2.66(16) . . . . ?
C3 C4 C5 C6 0.38(15) . . . . ?
C3 C4 C5 C10 179.52(10) . . . . ?
C3 C11 C12 C13 178.71(9) . . . . ?
C3 C11 C12 C15 -2.97(16) . . . . ?
C4 C3 C11 C12 -179.72(9) . . . . ?
C4 C5 C6 C1 -3.08(16) . . . . ?
C4 C5 C6 C7 178.52(10) . . . . ?
C4 C5 C10 C9 -178.53(10) . . . . ?
C5 C6 C7 C8 0.20(17) . . . . ?
C6 C1 C2 C3 -5.98(15) . . . . ?
C6 C1 C2 C16 174.97(9) . . . . ?
C6 C5 C10 C9 0.64(17) . . . . ?
C6 C7 C8 C9 0.22(18) . . . . ?
C7 C8 C9 C10 -0.20(19) . . . . ?
C8 C9 C10 C5 -0.23(19) . . . . ?
C10 C5 C6 C1 177.78(10) . . . . ?
C10 C5 C6 C7 -0.63(16) . . . . ?
C11 C3 C4 O2 -1.15(16) . . . . ?
C11 C3 C4 C5 -179.46(9) . . . . ?
C11 C12 C13 O3 17.18(15) . . . . ?
C11 C12 C13 O4 -161.01(10) . . . . ?
C11 C12 C15 C14 -176.91(10) . . . . ?
C11 C12 C15 C16 1.74(15) . . . . ?
C12 C15 C16 C2 1.05(16) . . . . ?
C13 C12 C15 C14 1.17(17) . . . . ?
C13 C12 C15 C16 179.82(10) . . . . ?
C14 C15 C16 C2 179.88(9) . . . . ?
C15 C12 C13 O3 -160.98(11) . . . . ?
C15 C12 C13 O4 20.82(16) . . . . ?
C16 C2 C3 C4 -177.47(9) . . . . ?
C16 C2 C3 C11 1.43(15) . . . . ?

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
-5 0 3 0.0971 -5.0000 -0.0000 3.0002 0.2662 -0.2557 -0.8858
5 0 -3 0.0971 5.0000 0.0000 -3.0002 -0.2662 0.2557 0.8858
-3 -5 -1 0.1297 -3.0000 -5.0000 -1.0000 0.6643 -0.6523 -0.1984
3 5 1 0.1297 3.0000 5.0000 1.0000 -0.6643 0.6523 0.1984
-3 5 5 0.1151 -3.0000 4.9999 5.0003 -0.3819 0.3265 -0.8758
3 -5 -5 0.1151 3.0000 -4.9999 -5.0003 0.3819 -0.3265 0.8758
1 6 -5 0.1463 1.0000 6.0001 -4.9998 0.0602 1.0162 -0.0067
-1 -6 5 0.0973 -1.0000 -6.0001 4.9998 -0.0602 -1.0162 0.0067
-2 6 -1 0.1266 -2.0000 6.0000 -0.9997 0.0161 0.7589 -0.5994
2 -6 1 0.1046 2.0000 -6.0000 0.9997 -0.0161 -0.7589 0.5994
4 1 -7 0.1351 4.0000 1.0001 -7.0001 0.1642 0.5480 0.7856
-4 -1 7 0.1351 -4.0000 -1.0001 7.0001 -0.1642 -0.5480 -0.7856
0 2 9 0.1173 0.0000 1.9999 9.0001 -0.9318 -0.1725 -0.3525
0 -2 -9 0.0973 -0.0000 -1.9999 -9.0001 0.9318 0.1725 0.3525
4 -1 3 0.1288 4.0000 -1.0000 2.9998 -0.6642 -0.1766 0.6095
-4 1 -3 0.0888 -4.0000 1.0000 -2.9998 0.6642 0.1766 -0.6095

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Li-H-aqdc_RT
_database_code_depnum_ccdc_archive 'CCDC 1419037'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H7 Li O6'
_chemical_formula_sum            'C16 H7 Li O6'
_chemical_formula_weight         302.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 O6 Li1 H5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0010 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.1681(4)
_cell_length_b                   10.6558(5)
_cell_length_c                   14.7002(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.680(5)
_cell_angle_gamma                90.00
_cell_volume                     1252.98(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2533
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3850
_cell_measurement_theta_min      5.1490
_exptl_absorpt_coefficient_mu    1.045
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.873
_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            'clear light yellow'
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.1601
_exptl_crystal_size_mid          0.1359
_exptl_crystal_size_min          0.0713
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5094
_diffrn_reflns_theta_full        70.68
_diffrn_reflns_theta_max         70.68
_diffrn_reflns_theta_min         5.16
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   33.00   58.00   1.0000    1.9800
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   48.00   76.00   1.0000    1.9800
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   19.00   44.00   1.0000    1.9800
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -24.00    3.00   1.0000    1.9800
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -42.00   18.00   1.0000    7.9200
omega____ theta____ kappa____ phi______ frames
    -      -54.7500    0.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega    7.00   78.00   1.0000    7.9200
omega____ theta____ kappa____ phi______ frames
    -       54.7500  -99.0000  -90.0000 71

#__ type_ start__ end____ width___ exp.time_
  7 omega   75.00  126.00   1.0000    7.9200
omega____ theta____ kappa____ phi______ frames
    -       54.7500  125.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega   76.00  102.00   1.0000    7.9200
omega____ theta____ kappa____ phi______ frames
    -       54.7500  125.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  -14.00   63.00   1.0000    7.9200
omega____ theta____ kappa____ phi______ frames
    -       54.7500  -37.0000  -90.0000 77

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00   70.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
 11 omega  144.00  178.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   12.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00  130.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   12.0000    0.0000 92

#__ type_ start__ end____ width___ exp.time_
 13 omega   60.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega   43.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 15 omega   43.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   36.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 17 omega   36.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
 18 omega   53.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
 20 omega   41.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -112.0000  -19.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   41.00   67.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   41.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 23 omega   45.00   70.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   35.00   63.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 25 omega   39.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   38.00   63.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   38.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
 28 omega   36.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000 -150.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1007518000
_diffrn_orient_matrix_UB_12      0.0492911000
_diffrn_orient_matrix_UB_13      -0.0931432000
_diffrn_orient_matrix_UB_21      0.0367410000
_diffrn_orient_matrix_UB_22      -0.1224635000
_diffrn_orient_matrix_UB_23      -0.0480421000
_diffrn_orient_matrix_UB_31      -0.1598341000
_diffrn_orient_matrix_UB_32      -0.0591555000
_diffrn_orient_matrix_UB_33      0.0216230000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2065
_reflns_number_total             2369
_reflns_odcompleteness_completeness 99.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_threshold_expression     >2sigma(I)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.1922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0993
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.61387(15) 0.55749(11) 0.64568(7) 0.0503(3) Uani 1 d . . .
O2 O 0.79910(14) 0.24020(9) 0.40076(7) 0.0430(3) Uani 1 d . . .
O3 O 0.99831(15) 0.58467(9) 0.24214(7) 0.0449(3) Uani 1 d . . .
O4 O 0.91741(16) 0.77874(10) 0.25077(7) 0.0538(3) Uani 1 d . . .
H4 H 0.8740 0.8420 0.2959 0.081 Uiso 1 d . . R
O5 O 0.84144(14) 0.91590(9) 0.36938(7) 0.0417(3) Uani 1 d . . .
O6 O 0.88256(14) 0.89746(9) 0.52192(7) 0.0441(3) Uani 1 d . . .
C1 C 0.66537(16) 0.48431(13) 0.59454(8) 0.0328(3) Uani 1 d . . .
C2 C 0.74107(15) 0.53144(12) 0.51667(8) 0.0288(3) Uani 1 d . . .
C3 C 0.78130(15) 0.44987(12) 0.44988(8) 0.0286(3) Uani 1 d . . .
C4 C 0.75921(16) 0.31177(12) 0.45769(9) 0.0315(3) Uani 1 d . . .
C5 C 0.69123(16) 0.26454(13) 0.53761(10) 0.0345(3) Uani 1 d . . .
C6 C 0.65003(16) 0.34692(13) 0.60409(9) 0.0335(3) Uani 1 d . . .
C7 C 0.58994(18) 0.29855(16) 0.67896(10) 0.0436(3) Uani 1 d . . .
H7 H 0.5625 0.3526 0.7232 0.052 Uiso 1 calc . . R
C8 C 0.5707(2) 0.17052(17) 0.68788(11) 0.0526(4) Uani 1 d . . .
H8 H 0.5310 0.1388 0.7382 0.063 Uiso 1 calc . . R
C9 C 0.6104(2) 0.08974(16) 0.62229(13) 0.0572(4) Uani 1 d . . .
H9 H 0.5970 0.0037 0.6285 0.069 Uiso 1 calc . . R
C10 C 0.6702(2) 0.13594(15) 0.54717(12) 0.0488(4) Uani 1 d . . .
H10 H 0.6963 0.0810 0.5031 0.059 Uiso 1 calc . . R
C11 C 0.84540(15) 0.49931(12) 0.37691(8) 0.0299(3) Uani 1 d . . .
H11 H 0.8744 0.4451 0.3332 0.036 Uiso 1 calc . . R
C12 C 0.86743(15) 0.62865(12) 0.36748(8) 0.0285(3) Uani 1 d . . .
C13 C 0.93367(17) 0.66527(12) 0.28201(9) 0.0331(3) Uani 1 d . . .
C14 C 0.85532(17) 0.85150(12) 0.44338(9) 0.0329(3) Uani 1 d . . .
C15 C 0.83103(15) 0.71003(12) 0.43667(8) 0.0286(3) Uani 1 d . . .
C16 C 0.76949(16) 0.65877(12) 0.51025(8) 0.0308(3) Uani 1 d . . .
H16 H 0.7468 0.7118 0.5564 0.037 Uiso 1 calc . . R
Li1 Li 1.0665(3) 0.9120(2) 0.62478(16) 0.0401(5) Uani 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 C1 1.2159(16) . ?
O2 C4 1.2242(16) . ?
O3 C13 1.2187(16) . ?
O4 H4 1.0563 . ?
O4 C13 1.2906(17) . ?
O5 H4 1.4049 . ?
O5 C14 1.2717(16) . ?
O6 C14 1.2323(16) . ?
C1 C2 1.4939(16) . ?
C1 C6 1.4785(19) . ?
C2 C3 1.3993(17) . ?
C2 C16 1.3830(18) . ?
C3 C4 1.4898(17) . ?
C3 C11 1.3892(17) . ?
C4 C5 1.4852(18) . ?
C5 C6 1.4042(19) . ?
C5 C10 1.392(2) . ?
C6 C7 1.3917(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.4004(18) . ?
C12 C13 1.5162(16) . ?
C12 C15 1.4132(17) . ?
C14 C15 1.5210(17) . ?
C15 C16 1.3933(17) . ?
C16 H16 0.9300 . ?

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
C13 O4 H4 113.4 . . ?
C14 O5 H4 110.9 . . ?
O1 C1 C2 120.45(12) . . ?
O1 C1 C6 122.00(12) . . ?
C6 C1 C2 117.51(11) . . ?
C3 C2 C1 121.41(12) . . ?
C16 C2 C1 118.90(11) . . ?
C16 C2 C3 119.68(11) . . ?
C2 C3 C4 120.68(11) . . ?
C11 C3 C2 119.01(12) . . ?
C11 C3 C4 120.30(11) . . ?
O2 C4 C3 120.63(12) . . ?
O2 C4 C5 121.57(12) . . ?
C5 C4 C3 117.78(11) . . ?
C6 C5 C4 121.29(12) . . ?
C10 C5 C4 119.15(13) . . ?
C10 C5 C6 119.56(13) . . ?
C5 C6 C1 121.07(11) . . ?
C7 C6 C1 119.48(13) . . ?
C7 C6 C5 119.44(14) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.36(15) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.15(14) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.41(16) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.08(16) . . ?
C9 C10 H10 120.0 . . ?
C3 C11 H11 119.1 . . ?
C3 C11 C12 121.72(11) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C13 114.19(11) . . ?
C11 C12 C15 118.86(11) . . ?
C15 C12 C13 126.92(11) . . ?
O3 C13 O4 120.82(12) . . ?
O3 C13 C12 118.63(12) . . ?
O4 C13 C12 120.51(12) . . ?
O5 C14 C15 119.44(11) . . ?
O6 C14 O5 123.71(12) . . ?
O6 C14 C15 116.82(11) . . ?
C12 C15 C14 127.67(11) . . ?
C16 C15 C12 118.66(11) . . ?
C16 C15 C14 113.64(11) . . ?
C2 C16 C15 121.97(11) . . ?
C2 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -171.63(13) . . . . ?
O1 C1 C2 C16 7.48(19) . . . . ?
O1 C1 C6 C5 172.04(13) . . . . ?
O1 C1 C6 C7 -6.4(2) . . . . ?
O2 C4 C5 C6 178.22(13) . . . . ?
O2 C4 C5 C10 -0.9(2) . . . . ?
O5 C14 C15 C12 31.2(2) . . . . ?
O5 C14 C15 C16 -150.57(12) . . . . ?
O6 C14 C15 C12 -151.05(13) . . . . ?
O6 C14 C15 C16 27.16(17) . . . . ?
C1 C2 C3 C4 -3.73(19) . . . . ?
C1 C2 C3 C11 177.51(11) . . . . ?
C1 C2 C16 C15 -176.38(11) . . . . ?
C1 C6 C7 C8 178.39(13) . . . . ?
C2 C1 C6 C5 -5.57(18) . . . . ?
C2 C1 C6 C7 176.02(12) . . . . ?
C2 C3 C4 O2 -177.81(12) . . . . ?
C2 C3 C4 C5 0.84(18) . . . . ?
C2 C3 C11 C12 -1.35(19) . . . . ?
C3 C2 C16 C15 2.74(19) . . . . ?
C3 C4 C5 C6 -0.42(19) . . . . ?
C3 C4 C5 C10 -179.58(13) . . . . ?
C3 C11 C12 C13 -178.18(11) . . . . ?
C3 C11 C12 C15 3.15(19) . . . . ?
C4 C3 C11 C12 179.89(11) . . . . ?
C4 C5 C6 C1 2.9(2) . . . . ?
C4 C5 C6 C7 -178.67(12) . . . . ?
C4 C5 C10 C9 178.58(15) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C1 C2 C3 6.02(18) . . . . ?
C6 C1 C2 C16 -174.87(11) . . . . ?
C6 C5 C10 C9 -0.6(2) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?
C10 C5 C6 C1 -177.93(13) . . . . ?
C10 C5 C6 C7 0.5(2) . . . . ?
C11 C3 C4 O2 0.93(19) . . . . ?
C11 C3 C4 C5 179.58(11) . . . . ?
C11 C12 C13 O3 -17.03(18) . . . . ?
C11 C12 C13 O4 161.01(13) . . . . ?
C11 C12 C15 C14 176.13(12) . . . . ?
C11 C12 C15 C16 -2.00(18) . . . . ?
C12 C15 C16 C2 -0.91(19) . . . . ?
C13 C12 C15 C14 -2.4(2) . . . . ?
C13 C12 C15 C16 179.52(12) . . . . ?
C14 C15 C16 C2 -179.29(12) . . . . ?
C15 C12 C13 O3 161.50(13) . . . . ?
C15 C12 C13 O4 -20.5(2) . . . . ?
C16 C2 C3 C4 177.16(11) . . . . ?
C16 C2 C3 C11 -1.60(19) . . . . ?

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 0 -9 0.0446 -0.0041 0.0046 -8.9893 0.8379 0.4312 -0.1940
0 0 9 0.0266 0.0041 -0.0046 8.9893 -0.8379 -0.4312 0.1940
-5 0 0 0.0679 -4.9985 0.0005 0.0066 0.5030 -0.1840 0.7991
5 0 0 0.0509 4.9985 -0.0005 -0.0066 -0.5030 0.1840 -0.7991
0 5 6 0.0695 0.0027 4.9918 5.9928 -0.3124 -0.8991 -0.1661
0 -5 -6 0.0695 -0.0027 -4.9918 -5.9928 0.3124 0.8991 0.1661
0 7 -2 0.0768 -0.0009 6.9939 -1.9978 0.5309 -0.7606 -0.4568
0 -7 2 0.0738 0.0009 -6.9939 1.9978 -0.5309 0.7606 0.4568

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_description       block
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3_Li2-15dhaq_120K
_database_code_depnum_ccdc_archive 'CCDC 1419038'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        'Dilithium 1,5-dihydroxyanthraquinone'
_chemical_formula_moiety         'C14 H10 Li2 O6'
_chemical_formula_sum            'C14 H10 Li2 O6'
_chemical_formula_weight         288.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Li2 C14 O6 H8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0010 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.0703(3)
_cell_length_b                   5.1497(2)
_cell_length_c                   14.7759(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.073(3)
_cell_angle_gamma                90.00
_cell_volume                     611.68(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4744
_cell_measurement_temperature    121(2)
_cell_measurement_theta_max      67.5890
_cell_measurement_theta_min      5.4580
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  0.866
_exptl_absorpt_correction_T_min  0.843
_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            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.1954
_exptl_crystal_size_mid          0.1792
_exptl_crystal_size_min          0.1761
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7318
_diffrn_reflns_theta_full        67.88
_diffrn_reflns_theta_max         67.88
_diffrn_reflns_theta_min         5.50
_diffrn_ambient_temperature      121(2)
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   39.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -1.4687  178.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega   35.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -1.4687  178.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        1.4687   57.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   36.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        1.4687  178.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
  5 omega  -84.00  -39.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  -61.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
  6 omega  -40.00  -10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  -86.0000  142.7899 30

#__ type_ start__ end____ width___ exp.time_
  7 omega -129.00  -45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  -61.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  8 omega  -85.00   19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844   61.0000   30.0000 104

#__ type_ start__ end____ width___ exp.time_
  9 omega   -3.00   22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844   45.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega  -64.00  -23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844   45.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
 11 omega  -65.00  -28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  -61.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 12 omega -128.00  -93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  -61.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
 13 omega  -96.00   25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844   77.0000 -150.0000 121

#__ type_ start__ end____ width___ exp.time_
 14 omega  -49.00    3.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844   61.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 15 omega -101.00  -62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  125.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
 16 omega  -90.00  -53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844   61.0000  150.0000 37

#__ type_ start__ end____ width___ exp.time_
 17 omega   63.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.4844   45.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.4844  -30.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega  123.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -21.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 20 omega  127.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   43.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
 21 omega   80.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   43.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 22 omega   91.00  135.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   43.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
 23 omega   51.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
 24 omega  112.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -21.0000  150.0000 65

#__ type_ start__ end____ width___ exp.time_
 25 omega   43.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -43.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 26 omega   28.00   57.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -32.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
 27 omega   30.00   68.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -32.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 28 omega   74.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   54.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
 29 omega   56.00  120.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -92.0000   17.8799 64

#__ type_ start__ end____ width___ exp.time_
 30 omega   26.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
 31 omega  127.00  172.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  104.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 32 omega   36.00   79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -54.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
 33 omega   77.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   43.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 34 omega   82.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   65.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
 35 omega   28.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
 36 omega   48.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -54.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 37 omega   27.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
 38 omega   75.00  161.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   54.0000   60.0000 86

#__ type_ start__ end____ width___ exp.time_
 39 omega   68.00  135.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   43.0000 -180.0000 67

#__ type_ start__ end____ width___ exp.time_
 40 omega   28.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 41 omega   51.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -54.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega   26.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
 43 omega  128.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   43.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
 44 omega  -82.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -1.4687  -77.0000 -120.0000 121

#__ type_ start__ end____ width___ exp.time_
 45 omega  -51.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -1.4687   37.0000    0.0000 129

#__ type_ start__ end____ width___ exp.time_
 46 omega  -33.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        1.4687   57.0000   60.0000 108

#__ type_ start__ end____ width___ exp.time_
 47 omega -136.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  -77.0000  -90.0000 121

#__ type_ start__ end____ width___ exp.time_
 48 omega -136.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  -77.0000 -120.0000 121

#__ type_ start__ end____ width___ exp.time_
 49 omega -130.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  -61.0000   90.0000 109

#__ type_ start__ end____ width___ exp.time_
 50 omega  -69.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844   30.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
 51 omega -122.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  125.0000 -180.0000 104

#__ type_ start__ end____ width___ exp.time_
 52 omega -136.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  -77.0000   60.0000 121

#__ type_ start__ end____ width___ exp.time_
 53 omega -136.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -55.4844  -77.0000    0.0000 121

#__ type_ start__ end____ width___ exp.time_
 54 omega   15.00  136.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.4844   77.0000    0.0000 121

#__ type_ start__ end____ width___ exp.time_
 55 omega   15.00  136.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.4844   77.0000 -120.0000 121

#__ type_ start__ end____ width___ exp.time_
 56 omega   -3.00   96.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.4844 -125.0000 -180.0000 99

#__ type_ start__ end____ width___ exp.time_
 57 omega   14.00  133.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.4844   45.0000  -30.0000 119

#__ type_ start__ end____ width___ exp.time_
 58 omega   73.00  136.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.4844  125.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
 59 omega   74.00  137.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   54.0000  -90.0000 63

#__ type_ start__ end____ width___ exp.time_
 60 omega   26.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000 -150.0000 61

#__ type_ start__ end____ width___ exp.time_
 61 omega   69.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   60.0000 109

#__ type_ start__ end____ width___ exp.time_
 62 omega   69.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -60.0000 109

#__ type_ start__ end____ width___ exp.time_
 63 omega   74.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   54.0000  150.0000 104

#__ type_ start__ end____ width___ exp.time_
 64 omega   69.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -180.0000 109

#__ type_ start__ end____ width___ exp.time_
 65 omega   74.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   65.0000   30.0000 104

#__ type_ start__ end____ width___ exp.time_
 66 omega   26.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
 67 omega   69.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -30.0000 109

#__ type_ start__ end____ width___ exp.time_
 68 omega   79.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  104.0000  -90.0000 99

#__ type_ start__ end____ width___ exp.time_
 69 omega   74.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   65.0000 -150.0000 16
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1421061000
_diffrn_orient_matrix_UB_12      0.1629321000
_diffrn_orient_matrix_UB_13      0.0339387000
_diffrn_orient_matrix_UB_21      0.0227248000
_diffrn_orient_matrix_UB_22      0.2034375000
_diffrn_orient_matrix_UB_23      -0.0743343000
_diffrn_orient_matrix_UB_31      -0.1264482000
_diffrn_orient_matrix_UB_32      -0.1466790000
_diffrn_orient_matrix_UB_33      -0.0655168000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1065
_reflns_number_total             1111
_reflns_odcompleteness_completeness 98.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0428P)²+0.2787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0812
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.66774(10) 0.55601(17) 0.49996(5) 0.0193(2) Uani 1 d . . .
O2 O 0.62523(10) 0.19556(17) 0.36342(6) 0.0193(2) Uani 1 d . . .
O3 O 0.45023(11) 0.74108(17) 0.32535(6) 0.0227(2) Uani 1 d . . .
H3A H 0.4300 0.7310 0.2640 0.034 Uiso 1 d . . R
H3B H 0.5110 0.8930 0.3385 0.034 Uiso 1 d . . R
C1 C 0.82087(14) 0.5282(2) 0.49602(8) 0.0158(3) Uani 1 d . . .
C2 C 0.88945(14) 0.3396(2) 0.43709(8) 0.0156(3) Uani 1 d . . .
C3 C 0.78633(14) 0.1736(2) 0.37791(8) 0.0166(3) Uani 1 d . . .
C4 C 0.86753(15) -0.0261(2) 0.33155(8) 0.0184(3) Uani 1 d . . .
H4 H 0.8021 -0.1426 0.2935 0.022 Uiso 1 calc . . R
C5 C 1.03685(15) -0.0549(2) 0.34025(8) 0.0194(3) Uani 1 d . . .
H5 H 1.0866 -0.1895 0.3081 0.023 Uiso 1 calc . . R
C6 C 1.13731(14) 0.1121(2) 0.39606(8) 0.0185(3) Uani 1 d . . .
H6 H 1.2547 0.0914 0.4013 0.022 Uiso 1 calc . . R
C7 C 1.06551(14) 0.3066(2) 0.44352(8) 0.0161(3) Uani 1 d . . .
Li1 Li 0.4957(2) 0.4607(4) 0.40814(14) 0.0210(4) Uani 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 C1 1.2506(15) . ?
O2 C3 1.3038(14) . ?
O3 H3A 0.9083 . ?
O3 H3B 0.9346 . ?
C1 C2 1.4469(17) . ?
C1 C7 1.4893(17) 3_766 ?
C2 C3 1.4348(17) . ?
C2 C7 1.4258(16) . ?
C3 C4 1.4267(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3692(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3993(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3794(17) . ?
C7 C1 1.4892(17) 3_766 ?

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
H3A O3 H3B 107.5 . . ?
O1 C1 C2 122.48(11) . . ?
O1 C1 C7 117.73(11) . 3_766 ?
C2 C1 C7 119.78(11) . 3_766 ?
C3 C2 C1 122.31(11) . . ?
C7 C2 C1 118.15(11) . . ?
C7 C2 C3 119.38(11) . . ?
O2 C3 C2 124.38(11) . . ?
O2 C3 C4 118.51(11) . . ?
C4 C3 C2 117.11(11) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.00(11) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.67(11) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.88(11) . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C1 121.94(11) . 3_766 ?
C6 C7 C1 117.12(11) . 3_766 ?
C6 C7 C2 120.90(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 0.96(18) . . . . ?
O1 C1 C2 C7 -174.43(10) . . . . ?
O2 C3 C4 C5 177.25(11) . . . . ?
C1 C2 C3 O2 8.32(18) . . . . ?
C1 C2 C3 C4 -172.39(10) . . . . ?
C1 C2 C7 C1 -4.19(18) . . . 3_766 ?
C1 C2 C7 C6 173.33(10) . . . . ?
C2 C3 C4 C5 -2.09(17) . . . . ?
C3 C2 C7 C1 -179.73(10) . . . 3_766 ?
C3 C2 C7 C6 -2.21(17) . . . . ?
C3 C4 C5 C6 0.36(18) . . . . ?
C4 C5 C6 C7 0.52(18) . . . . ?
C5 C6 C7 C1 178.06(10) . . . 3_766 ?
C5 C6 C7 C2 0.43(18) . . . . ?
C7 C1 C2 C3 179.49(10) 3_766 . . . ?
C7 C1 C2 C7 4.10(18) 3_766 . . . ?
C7 C2 C3 O2 -176.34(10) . . . . ?
C7 C2 C3 C4 2.96(16) . . . . ?

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
-5 0 0 0.0896 -5.0035 0.0034 0.0014 0.7116 -0.1131 0.6321
5 0 0 0.0896 5.0035 -0.0034 -0.0014 -0.7116 0.1131 -0.6321
0 -2 -7 0.0837 0.0049 -1.9983 -6.9937 -0.5637 0.1134 0.7507
0 0 -10 0.0761 0.0045 0.0010 -9.9952 -0.3397 0.7433 0.6541
0 0 10 0.1001 -0.0045 -0.0010 9.9952 0.3397 -0.7433 -0.6541
-1 -3 4 0.0897 -0.9998 -2.9982 4.0028 -0.2106 -0.9302 0.3039
1 3 -4 0.0897 0.9998 2.9982 -4.0028 0.2106 0.9302 -0.3039
0 3 1 0.0918 -0.0032 2.9984 0.9951 0.5228 0.5360 -0.5046
0 -3 -1 0.0918 0.0032 -2.9984 -0.9951 -0.5228 -0.5360 0.5046

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3_Li2-15dhaq_120K
_database_code_depnum_ccdc_archive 'CCDC 1419039'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        '1,5-Dihydroxyanthraquinone dilithium hydrate'
_chemical_formula_moiety         'C7 H5 Li O3'
_chemical_formula_sum            'C7 H5 Li O3'
_chemical_formula_weight         144.05
_chemical_melting_point          ?
_chemical_oxdiff_formula         'O3 Li C7 H5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0010 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.0719(3)
_cell_length_b                   5.1821(2)
_cell_length_c                   14.8188(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.926(3)
_cell_angle_gamma                90.00
_cell_volume                     617.57(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    302
_cell_measurement_theta_max      70.4890
_cell_measurement_theta_min      5.4420
_exptl_absorpt_coefficient_mu    1.004
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.690
_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            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.6061
_exptl_crystal_size_mid          0.2495
_exptl_crystal_size_min          0.0144
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3334
_diffrn_reflns_theta_full        70.65
_diffrn_reflns_theta_max         70.65
_diffrn_reflns_theta_min         5.50
_diffrn_ambient_temperature      302
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   34.00   60.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   11.00   38.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   38.00   73.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega  -88.00  -29.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -77.0000  -30.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega  -92.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  125.0000    0.0000 49

#__ type_ start__ end____ width___ exp.time_
  6 omega -119.00  -38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -57.0000  -90.0000 81

#__ type_ start__ end____ width___ exp.time_
  7 omega    1.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7500 -125.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega   75.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7500  125.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
  9 omega   91.00  121.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7500  125.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00   73.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
 11 omega   42.00   71.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 12 omega   86.00  128.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 13 omega   46.00  111.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000    0.0000 65

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00   87.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
 15 omega   37.00   74.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
 16 omega  107.00  176.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   63.0000 -120.0000 69

#__ type_ start__ end____ width___ exp.time_
 17 omega   51.00   77.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00   66.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   65.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00   67.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 21 omega   38.00   70.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
 22 omega  122.00  175.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   63.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 23 omega   35.00   60.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   37.00   70.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
 25 omega  -22.00   69.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 91

#__ type_ start__ end____ width___ exp.time_
 26 omega  -22.00   69.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
 27 omega -126.00  -23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -77.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 28 omega  -76.00   14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7500   57.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 29 omega -126.00  -23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 30 omega -124.00  -33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -57.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
 31 omega -126.00  -54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -77.0000  150.0000 72
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0060940000
_diffrn_orient_matrix_UB_12      0.2888212000
_diffrn_orient_matrix_UB_13      0.0240445000
_diffrn_orient_matrix_UB_21      -0.1811052000
_diffrn_orient_matrix_UB_22      0.0140701000
_diffrn_orient_matrix_UB_23      -0.0419092000
_diffrn_orient_matrix_UB_31      -0.0620256000
_diffrn_orient_matrix_UB_32      -0.0689786000
_diffrn_orient_matrix_UB_33      0.0925028000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1047
_reflns_number_total             1166
_reflns_odcompleteness_completeness 98.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_threshold_expression     >2sigma(I)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0616P)²+0.1037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1017
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.33184(10) 1.05471(19) 0.49968(6) 0.0283(3) Uani 1 d . . .
O2 O 0.37339(11) 0.69727(18) 0.63604(6) 0.0283(3) Uani 1 d . . .
O3 O 0.54687(13) 1.24058(19) 0.67456(7) 0.0366(3) Uani 1 d . . .
H3A H 0.5710 1.2360 0.7366 0.055 Uiso 1 d . . R
H3B H 0.4850 1.3940 0.6607 0.055 Uiso 1 d . . R
C1 C 0.17904(15) 1.0271(2) 0.50392(8) 0.0205(3) Uani 1 d . . .
C2 C 0.11000(14) 0.8414(2) 0.56268(8) 0.0199(3) Uani 1 d . . .
C3 C 0.21289(15) 0.6761(2) 0.62189(8) 0.0219(3) Uani 1 d . . .
C4 C 0.13083(17) 0.4791(3) 0.66818(9) 0.0266(3) Uani 1 d . . .
H4 H 0.1944 0.3660 0.7056 0.032 Uiso 1 calc . . R
C5 C -0.03763(17) 0.4507(3) 0.65949(9) 0.0285(3) Uani 1 d . . .
H5 H -0.0865 0.3196 0.6909 0.034 Uiso 1 calc . . R
C6 C -0.13775(16) 0.6162(3) 0.60390(9) 0.0265(3) Uani 1 d . . .
H6 H -0.2527 0.5966 0.5990 0.032 Uiso 1 calc . . R
C7 C -0.06567(15) 0.8085(2) 0.55643(8) 0.0207(3) Uani 1 d . . .
Li1 Li 0.5030(3) 0.9616(5) 0.59187(15) 0.0289(5) Uani 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 C1 1.2486(15) . ?
O2 C3 1.2992(15) . ?
O3 H3A 0.9235 . ?
O3 H3B 0.9517 . ?
C1 C2 1.4414(17) . ?
C1 C7 1.4909(17) 3_576 ?
C2 C3 1.4382(17) . ?
C2 C7 1.4233(16) . ?
C3 C4 1.4246(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.3628(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.3976(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.3771(18) . ?
C7 C1 1.4910(17) 3_576 ?

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
H3A O3 H3B 107.4 . . ?
O1 C1 C2 122.81(11) . . ?
O1 C1 C7 117.54(11) . 3_576 ?
C2 C1 C7 119.64(11) . 3_576 ?
C3 C2 C1 122.22(11) . . ?
C7 C2 C1 118.39(11) . . ?
C7 C2 C3 119.22(11) . . ?
O2 C3 C2 124.32(11) . . ?
O2 C3 C4 118.77(11) . . ?
C4 C3 C2 116.91(11) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.23(12) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.74(12) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.80(12) . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C1 121.82(11) . 3_576 ?
C6 C7 C1 117.10(11) . 3_576 ?
C6 C7 C2 121.05(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 0.87(19) . . . . ?
O1 C1 C2 C7 -174.31(11) . . . . ?
O2 C3 C4 C5 177.52(12) . . . . ?
C1 C2 C3 O2 8.32(19) . . . . ?
C1 C2 C3 C4 -172.38(11) . . . . ?
C1 C2 C7 C1 -4.46(19) . . . 3_576 ?
C1 C2 C7 C6 173.27(11) . . . . ?
C2 C3 C4 C5 -1.82(19) . . . . ?
C3 C2 C7 C1 -179.78(11) . . . 3_576 ?
C3 C2 C7 C6 -2.05(18) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C5 C6 C7 C1 178.08(11) . . . 3_576 ?
C5 C6 C7 C2 0.25(19) . . . . ?
C7 C1 C2 C3 179.54(11) 3_576 . . . ?
C7 C1 C2 C7 4.37(19) 3_576 . . . ?
C7 C2 C3 O2 -176.55(11) . . . . ?
C7 C2 C3 C4 2.76(17) . . . . ?

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
-2 0 9 0.1165 -1.9986 0.0006 9.0032 0.2288 -0.0153 0.9567
2 0 -9 0.1165 1.9986 -0.0006 -9.0032 -0.2288 0.0153 -0.9567
0 3 0 0.2692 0.0058 3.0000 0.0041 0.8665 0.0410 -0.2069
-1 -3 3 0.3118 -1.0053 -2.9997 2.9971 -0.7882 0.0142 0.5465
1 -3 -3 0.3148 0.9937 -3.0003 -3.0053 -0.9449 -0.0962 -0.1327
-5 0 0 0.0062 -4.9989 0.0009 0.0022 0.0308 0.9052 0.3102
5 0 0 0.0082 4.9989 -0.0009 -0.0022 -0.0308 -0.9052 -0.3102

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_description       hexagonal
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_st345-Cu-120K_abs3
_database_code_depnum_ccdc_archive 'CCDC 1419040'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        'Dilithium quinizarin'
_chemical_formula_moiety         '0.5(C28 H20 Li4 O12)'
_chemical_formula_sum            'C14 H10 Li2 O6'
_chemical_formula_weight         288.11
_chemical_oxdiff_formula         'Li2 C14 O6 H10'
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
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
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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z+1/2
3 -x,y+1/2,-z
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z-1/2
7 x,-y-1/2,z
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      62
_cell_length_a                   7.1641(3)
_cell_length_b                   16.1044(9)
_cell_length_c                   10.7351(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1238.55(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    121.7(9)
_cell_measurement_theta_max      61.8650
_cell_measurement_theta_min      4.9170
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.851
_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            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.5450
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             594.1934
_exptl_crystal_size_max          0.2504
_exptl_crystal_size_mid          0.2244
_exptl_crystal_size_min          0.1173
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5661
_diffrn_reflns_theta_full        61.83
_diffrn_reflns_theta_max         61.83
_diffrn_reflns_theta_min         4.95
_diffrn_ambient_temperature      121.7(9)
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9980
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   10.00   35.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -      -33.4680    0.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
  2 omega -108.00  -69.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -      -33.4680 -178.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   55.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       33.4680   77.0000   60.0000 102

#__ type_ start__ end____ width___ exp.time_
  4 omega   57.00  104.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       33.4680   77.0000   60.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega   28.00   78.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
  6 omega   45.00   73.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
  7 omega   28.00   68.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
  8 omega   31.00   66.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   20.00   56.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  150.0000 72

#__ type_ start__ end____ width___ exp.time_
 10 omega   26.00   67.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
 11 omega   82.00  140.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   60.0000 116

#__ type_ start__ end____ width___ exp.time_
 12 omega   30.00   56.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -33.0000  -34.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega -106.00   -8.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -      -33.4680  -37.0000  -60.0000 196

#__ type_ start__ end____ width___ exp.time_
 14 omega -102.00  -12.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -      -33.4680  -57.0000 -120.0000 180

#__ type_ start__ end____ width___ exp.time_
 15 omega  -39.00   59.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       33.4680  -37.0000  -60.0000 196

#__ type_ start__ end____ width___ exp.time_
 16 omega   61.00  163.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000 -180.0000 204

#__ type_ start__ end____ width___ exp.time_
 17 omega   61.00  163.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  -30.0000 204

#__ type_ start__ end____ width___ exp.time_
 18 omega   69.00  159.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000   30.0000 180

#__ type_ start__ end____ width___ exp.time_
 19 omega   69.00   97.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
 20 omega   18.00   69.00   0.5000    1.4700
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000    0.0000 102
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1962226000
_diffrn_orient_matrix_UB_12      0.0284075000
_diffrn_orient_matrix_UB_13      -0.0405400000
_diffrn_orient_matrix_UB_21      0.0804906000
_diffrn_orient_matrix_UB_22      -0.0311554000
_diffrn_orient_matrix_UB_23      0.1245866000
_diffrn_orient_matrix_UB_31      0.0356416000
_diffrn_orient_matrix_UB_32      -0.0859161000
_diffrn_orient_matrix_UB_33      -0.0583630000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              0
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                948
_reflns_number_total             1008
_reflns_odcompleteness_completeness 98.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_reflns_threshold_expression     I>=2u(I)
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.2102
_refine_diff_density_min         -0.2433
_refine_diff_density_rms         0.0668
_refine_ls_d_res_high            0.8745
_refine_ls_d_res_low             8.9324
_refine_ls_goodness_of_fit_ref   1.0348
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    9
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.0348
_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)+(0.0480P)²+2.4823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1375
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O3(H3a,H3b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C7(H7)
;
_atom_sites_solution_primary     iterative
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 0.4753(3) 0.58214(12) 0.4713(2) 0.0439(6) Uani 1.000000 .
O2 O 0.7936(3) 0.58037(12) 0.6029(2) 0.0394(6) Uani 1.000000 .
O3 O 0.8485(3) 0.48350(15) 0.3438(2) 0.0546(7) Uani 1.000000 .
H3a H 0.9599(3) 0.45602(15) 0.3599(2) 0.0820(10) Uiso 1.000000 R
H3b H 0.8119(3) 0.46902(15) 0.2619(2) 0.0820(10) Uiso 1.000000 R
C1 C 0.4772(4) 0.65993(17) 0.4842(3) 0.0324(7) Uani 1.000000 .
C2 C 0.6294(3) 0.70458(16) 0.5398(2) 0.0290(6) Uani 1.000000 .
C3 C 0.7755(4) 0.65999(17) 0.6006(3) 0.0324(7) Uani 1.000000 .
C4 C 0.9109(4) 0.70864(18) 0.6667(3) 0.0394(7) Uani 1.000000 .
H4 H 1.0050(4) 0.68053(18) 0.7127(3) 0.0472(9) Uiso 1.000000 R
C5 C 0.3125(4) 0.70679(17) 0.4412(3) 0.0323(7) Uani 1.000000 .
C6 C 0.1583(4) 0.6638(2) 0.3935(3) 0.0394(7) Uani 1.000000 .
H6 H 0.1583(4) 0.6048(2) 0.3923(3) 0.0473(9) Uiso 1.000000 R
C7 C 0.0059(4) 0.7072(2) 0.3481(3) 0.0429(8) Uani 1.000000 .
H7 H -0.0992(4) 0.6778(2) 0.3168(3) 0.0514(9) Uiso 1.000000 R
Li1 Li 0.6853(7) 0.5103(3) 0.4805(6) 0.0465(13) Uani 1.000000 .


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 C1 1.260(3) . ?
O1 Li1 1.952(6) 5_666 ?
O1 Li1 1.900(5) . ?
O2 C3 1.289(3) . ?
O2 Li1 1.897(6) . ?
O3 H3a 0.9288 . ?
O3 H3b 0.9466 . ?
O3 Li1 1.925(6) . ?
C1 C2 1.436(4) . ?
C1 C5 1.475(4) . ?
C2 C2 1.463(5) 7_575 ?
C2 C3 1.427(4) . ?
C3 C4 1.435(4) . ?
C4 C4 1.332(6) 7_575 ?
C4 H4 0.9500 . ?
C5 C5 1.392(5) 7_575 ?
C5 C6 1.401(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(4) . ?
C7 C7 1.380(6) 7_575 ?
C7 H7 0.9500 . ?
Li1 Li1 2.709(10) 5_666 ?

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
Li1 O1 C1 137.4(2) 5_666 . ?
Li1 O1 C1 126.2(2) . . ?
Li1 O2 C3 122.5(2) . . ?
H3b O3 H3a 107.1 . . ?
Li1 O3 H3a 119.1 . . ?
Li1 O3 H3b 126.5 . . ?
C2 C1 O1 123.5(2) . . ?
C5 C1 O1 117.7(2) . . ?
C5 C1 C2 118.8(2) . . ?
C2 C2 C1 120.07(16) 7_575 . ?
C3 C2 C1 119.7(2) . . ?
C2 C3 O2 125.7(2) . . ?
C4 C3 O2 117.7(2) . . ?
C4 C3 C2 116.6(3) . . ?
C4 C4 C3 123.09(16) 7_575 . ?
H4 C4 C3 118.46(16) . . ?
C5 C5 C1 120.78(15) 7_575 . ?
C6 C5 C1 119.5(3) . . ?
H6 C6 C5 119.94(17) . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 119.94(18) . . ?
C7 C7 C6 120.27(18) 7_575 . ?
H7 C7 C6 119.87(18) . . ?
O2 Li1 O1 120.8(3) . 5_666 ?
O2 Li1 O1 89.9(2) . . ?
O3 Li1 O1 112.9(3) . 5_666 ?
O3 Li1 O1 125.3(3) . . ?
O3 Li1 O2 114.4(3) . . ?
Li1 Li1 O1 44.54(16) 5_666 5_666 ?
Li1 Li1 O1 46.10(16) 5_666 . ?
Li1 Li1 O2 111.6(3) 5_666 . ?
Li1 Li1 O3 133.2(4) 5_666 . ?

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
-1 8 -4 0.0586 -0.9939 8.0044 -4.0120 0.1950 -0.8292 -0.4890
1 -8 4 0.0586 0.9939 -8.0044 4.0120 -0.1950 0.8292 0.4890
4 -4 -2 0.0732 3.9951 -4.0001 -1.9893 0.7509 0.1983 0.6022
-4 4 2 0.1012 -3.9951 4.0001 1.9893 -0.7509 -0.1983 -0.6022
1 10 3 0.0710 1.0154 9.9971 2.9714 0.3628 0.1405 -0.9961
-4 -7 -1 0.0815 -4.0113 -6.9975 -0.9803 -0.9461 -0.2270 0.5154
2 -9 -3 0.0656 1.9871 -8.9985 -2.9751 0.2549 0.0696 1.0176

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_st345-hex_Cu_RT_red2_abs_centro
_database_code_depnum_ccdc_archive 'CCDC 1419041'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        '1,4-dihydroxyanthraquinone dilithium hydrate'
_chemical_formula_moiety         'C7 H5 Li O3'
_chemical_formula_sum            'C7 H5 Li O3'
_chemical_formula_weight         144.06
_chemical_oxdiff_formula         'C14 O6 Li2 H10'
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
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
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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z+1/2
3 -x,y+1/2,-z
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z-1/2
7 x,-y-1/2,z
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      62
_cell_length_a                   7.1681(3)
_cell_length_b                   16.0902(6)
_cell_length_c                   10.7456(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1239.36(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3608
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.4890
_cell_measurement_theta_min      4.9200
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.795
_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            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.5440
_exptl_crystal_F_000             594.1934
_exptl_crystal_size_max          0.3522
_exptl_crystal_size_mid          0.2578
_exptl_crystal_size_min          0.1832
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5756
_diffrn_reflns_theta_full        70.8452
_diffrn_reflns_theta_max         70.85
_diffrn_reflns_theta_min         4.95
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.9871
_diffrn_measured_fraction_theta_max 0.9871
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   32.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   38.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -30.00   11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   84.0000 -124.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega -127.00   -2.00   1.0000    1.1400
omega____ theta____ kappa____ phi______ frames
    -      -54.7500    0.0000   30.0000 125

#__ type_ start__ end____ width___ exp.time_
  5 omega   86.00  122.00   1.0000    1.1400
omega____ theta____ kappa____ phi______ frames
    -       54.7500  125.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega   81.00  106.00   1.0000    1.1400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   86.0000  -19.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   74.00  114.00   1.0000    1.1400
omega____ theta____ kappa____ phi______ frames
    -       54.7500  125.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  8 omega   -5.00   76.00   1.0000    1.1400
omega____ theta____ kappa____ phi______ frames
    -       54.7500  -57.0000 -120.0000 81

#__ type_ start__ end____ width___ exp.time_
  9 omega  107.00  133.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   95.00  164.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000   63.0000    0.0000 69

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   62.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   43.00   69.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   69.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
 14 omega   73.00  132.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -63.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
 15 omega   43.00   71.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
 16 omega   58.00   87.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 17 omega   60.00   86.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   40.00   71.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
 19 omega   38.00   65.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   88.00  129.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -63.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   66.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 22 omega   39.00   64.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   49.00   78.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
 24 omega   63.00   90.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   40.00   76.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
 26 omega   36.00   67.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 27 omega   78.00  105.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -63.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 28 omega  109.00  134.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -63.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega  126.00  177.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000   50.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
 30 omega   40.00   80.00   1.0000   20.4300
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
 31 omega   32.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
 32 omega  -27.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 33 omega -124.00  -37.00   1.0000    1.1400
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -57.0000  -90.0000 87
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1007037000
_diffrn_orient_matrix_UB_12      -0.0831408000
_diffrn_orient_matrix_UB_13      0.0236480000
_diffrn_orient_matrix_UB_21      -0.0966833000
_diffrn_orient_matrix_UB_22      0.0071467000
_diffrn_orient_matrix_UB_23      -0.1275083000
_diffrn_orient_matrix_UB_31      0.1633933000
_diffrn_orient_matrix_UB_32      -0.0469478000
_diffrn_orient_matrix_UB_33      -0.0611312000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              0
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1189
_reflns_number_total             1226
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_threshold_expression     I>=2u(I)
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.2427
_refine_diff_density_min         -0.2073
_refine_diff_density_rms         0.0573
_refine_ls_d_res_high            0.8161
_refine_ls_d_res_low             8.9361
_refine_ls_goodness_of_fit_ref   1.0463
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    9
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.0463
_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)+(0.0426P)²+1.7571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1305
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O3(H3a,H3b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C4(H4)
;
_atom_sites_solution_primary     iterative
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
O2 O 0.7064(2) 0.58042(9) 0.60302(16) 0.0375(4) Uani 1.000000 .
O1 O 1.0248(2) 0.58223(10) 0.47127(17) 0.0420(5) Uani 1.000000 .
O3 O 0.6515(2) 0.48339(13) 0.34404(17) 0.0532(5) Uani 1.000000 .
H3a H 0.6960(2) 0.46901(13) 0.26505(17) 0.0799(8) Uiso 1.000000 R
H3b H 0.5350(2) 0.46101(13) 0.36003(17) 0.0799(8) Uiso 1.000000 R
C3 C 0.7248(3) 0.66001(14) 0.60046(19) 0.0305(5) Uani 1.000000 .
C1 C 1.0227(3) 0.66008(14) 0.4843(2) 0.0309(5) Uani 1.000000 .
C2 C 0.8706(3) 0.70454(12) 0.53988(19) 0.0278(5) Uani 1.000000 .
C5 C 1.1874(3) 0.70662(13) 0.4412(2) 0.0306(5) Uani 1.000000 .
C6 C 1.3416(3) 0.66406(16) 0.3933(2) 0.0371(5) Uani 1.000000 .
H6 H 1.3415(3) 0.60627(16) 0.3920(2) 0.0445(6) Uiso 1.000000 R
C7 C 1.4933(3) 0.70673(16) 0.3482(2) 0.0418(6) Uani 1.000000 .
H7 H 1.5959(3) 0.67781(16) 0.3177(2) 0.0501(7) Uiso 1.000000 R
C4 C 0.5894(3) 0.70851(15) 0.6670(2) 0.0392(6) Uani 1.000000 .
H4 H 0.4976(3) 0.68089(15) 0.7121(2) 0.0470(7) Uiso 1.000000 R
Li1 Li 0.8140(5) 0.5103(3) 0.4804(4) 0.0420(10) Uani 1.000000 .


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
O2 C3 1.288(3) . ?
O2 Li1 1.898(5) . ?
O1 C1 1.260(3) . ?
O1 Li1 1.906(4) . ?
O1 Li1 1.955(4) 5_766 ?
O3 H3a 0.9358 . ?
O3 H3b 0.9255 . ?
O3 Li1 1.921(5) . ?
C3 C2 1.424(3) . ?
C3 C4 1.436(3) . ?
C1 C2 1.434(3) . ?
C1 C5 1.473(3) . ?
C2 C2 1.463(4) 7_575 ?
C5 C5 1.396(4) 7_575 ?
C5 C6 1.398(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(3) . ?
C7 C7 1.393(5) 7_575 ?
C7 H7 0.9300 . ?
C4 C4 1.335(5) 7_575 ?
C4 H4 0.9300 . ?
Li1 Li1 2.720(8) 5_766 ?

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
Li1 O2 C3 122.32(19) . . ?
Li1 O1 C1 137.3(2) 5_766 . ?
Li1 O1 C1 126.01(19) . . ?
H3b O3 H3a 112.3 . . ?
Li1 O3 H3a 122.7 . . ?
Li1 O3 H3b 119.5 . . ?
C2 C3 O2 125.82(19) . . ?
C4 C3 O2 117.40(19) . . ?
C4 C3 C2 116.8(2) . . ?
C2 C1 O1 123.5(2) . . ?
C5 C1 O1 117.43(19) . . ?
C5 C1 C2 119.1(2) . . ?
C1 C2 C3 119.80(19) . . ?
C2 C2 C3 120.20(12) 7_575 . ?
C2 C2 C1 119.92(12) 7_575 . ?
C5 C5 C1 120.57(12) 7_575 . ?
C6 C5 C1 120.0(2) . . ?
H6 C6 C5 119.65(14) . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.65(15) . . ?
C7 C7 C6 119.97(15) 7_575 . ?
H7 C7 C6 120.01(15) . . ?
C4 C4 C3 122.91(12) 7_575 . ?
H4 C4 C3 118.55(13) . . ?
O1 Li1 O2 120.6(2) 5_766 . ?
O1 Li1 O2 89.83(19) . . ?
O3 Li1 O2 114.6(2) . . ?
O3 Li1 O1 112.9(2) . 5_766 ?
O3 Li1 O1 125.3(3) . . ?
Li1 Li1 O2 111.3(3) 5_766 . ?
Li1 Li1 O1 44.49(13) 5_766 5_766 ?
Li1 Li1 O1 45.94(13) 5_766 . ?
Li1 Li1 O3 133.2(3) 5_766 . ?

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 0 -7 0.1238 -0.0026 0.0156 -6.9939 -0.1664 0.8921 0.4264
0 0 7 0.1438 0.0026 -0.0156 6.9939 0.1664 -0.8921 -0.4264
-4 2 -4 0.1291 -4.0071 2.0101 -3.9932 0.1420 0.9110 -0.5050
4 -2 4 0.1291 4.0071 -2.0101 3.9932 -0.1420 -0.9110 0.5050
4 0 -4 0.1029 4.0045 0.0027 -3.9986 -0.4981 0.1227 0.8986
-4 0 4 0.1549 -4.0045 -0.0027 3.9986 0.4981 -0.1227 -0.8986
0 10 -1 0.0916 0.0009 9.9775 -0.9929 -0.8531 0.1978 -0.4076
0 -10 1 0.0916 -0.0009 -9.9775 0.9929 0.8531 -0.1978 0.4076

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_description       hexagonal
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5_Li-H-14dhaq_120K
_database_code_depnum_ccdc_archive 'CCDC 1419042'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        '1,4-dihydroxyanthraquinone lithium hydrate'
_chemical_formula_moiety         'C14 H9 Li O5'
_chemical_formula_sum            'C14 H9 Li O5'
_chemical_formula_weight         264.15
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 O5 Li H9'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0010 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   3.8011(2)
_cell_length_b                   15.9753(11)
_cell_length_c                   18.0272(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1094.68(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1322
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      60.9910
_cell_measurement_theta_min      3.7050
_exptl_absorpt_coefficient_mu    1.020
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.762
_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            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.7928
_exptl_crystal_size_mid          0.0293
_exptl_crystal_size_min          0.0239
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3502
_diffrn_reflns_theta_full        61.10
_diffrn_reflns_theta_max         61.10
_diffrn_reflns_theta_min         3.70
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -105.00  -53.00   1.0000   11.4100
omega____ theta____ kappa____ phi______ frames
    -      -32.2456  178.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega -107.00  -61.00   1.0000   11.4100
omega____ theta____ kappa____ phi______ frames
    -      -32.2456 -178.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega   56.00  107.00   1.0000   11.4100
omega____ theta____ kappa____ phi______ frames
    -       32.2456  178.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
  4 omega  -47.00   -4.00   1.0000   45.6400
omega____ theta____ kappa____ phi______ frames
    -      -75.0000   45.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega  110.00  143.00   1.0000   45.6400
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega   42.00  128.00   1.0000   45.6400
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -87.0000   -4.9788 86

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00   71.00   1.0000   45.6400
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   81.00  156.00   1.0000   45.6400
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000   60.0000 75

#__ type_ start__ end____ width___ exp.time_
  9 omega   66.00  144.00   1.0000   45.6400
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000  -90.0000 78

#__ type_ start__ end____ width___ exp.time_
 10 omega   61.00   89.00   1.0000   45.6400
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 11 omega   -3.00   24.00   1.0000   11.4100
omega____ theta____ kappa____ phi______ frames
    -       32.2456   84.0000  174.1209 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   11.00  101.00   1.0000   11.4100
omega____ theta____ kappa____ phi______ frames
    -       32.2456   57.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 13 omega   69.00  160.00   1.0000   45.6400
omega____ theta____ kappa____ phi______ frames
    -       90.5000   56.0000  -35.0000 91

#__ type_ start__ end____ width___ exp.time_
 14 omega   67.00  112.00   1.0000   45.6400
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  150.0000 45
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.2500557000
_diffrn_orient_matrix_UB_12      -0.0196852000
_diffrn_orient_matrix_UB_13      0.0650367000
_diffrn_orient_matrix_UB_21      0.2724089000
_diffrn_orient_matrix_UB_22      0.0617015000
_diffrn_orient_matrix_UB_23      -0.0318485000
_diffrn_orient_matrix_UB_31      -0.1665659000
_diffrn_orient_matrix_UB_32      0.0713276000
_diffrn_orient_matrix_UB_33      0.0454201000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1439
_reflns_number_total             1622
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_threshold_expression     >2sigma(I)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1622
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1017P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1488
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(4) 0.1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3.a Riding coordinates:
 O2(H2), O5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.3949(7) 0.53782(15) 0.22224(12) 0.0401(7) Uani 1 d . . .
O2 O 0.0925(8) 0.41495(15) 0.16560(12) 0.0409(7) Uani 1 d . . .
H2 H 0.2308 0.4659 0.1710 0.061 Uiso 1 d . . R
O3 O -0.1306(7) 0.28148(14) 0.44112(12) 0.0343(6) Uani 1 d . . .
O4 O 0.2679(7) 0.40893(14) 0.49839(12) 0.0344(6) Uani 1 d . . .
O5 O -0.2474(7) 0.36997(15) 0.61178(12) 0.0374(7) Uani 1 d . . .
H5A H -0.4180 0.3970 0.5821 0.056 Uiso 1 d . . R
H5B H -0.1600 0.4080 0.6474 0.056 Uiso 1 d . . R
C1 C 0.3474(9) 0.5090(2) 0.28613(17) 0.0304(8) Uani 1 d . . .
C2 C 0.1701(9) 0.4298(2) 0.29744(18) 0.0282(7) Uani 1 d . . .
C3 C 0.0467(9) 0.3869(2) 0.23524(18) 0.0316(8) Uani 1 d . . .
C4 C -0.1325(9) 0.3104(2) 0.24356(17) 0.0308(8) Uani 1 d . . .
H4 H -0.2181 0.2818 0.2010 0.037 Uiso 1 calc . . R
C5 C -0.1841(9) 0.2770(2) 0.31208(18) 0.0314(8) Uani 1 d . . .
H5 H -0.3062 0.2253 0.3162 0.038 Uiso 1 calc . . R
C6 C -0.0598(9) 0.3174(2) 0.37888(17) 0.0282(8) Uani 1 d . . .
C7 C 0.2678(9) 0.4374(2) 0.43410(17) 0.0279(8) Uani 1 d . . .
C8 C 0.1242(9) 0.3947(2) 0.37074(18) 0.0285(7) Uani 1 d . . .
C9 C 0.4275(10) 0.5218(2) 0.42262(19) 0.0303(8) Uani 1 d . . .
C10 C 0.4686(9) 0.5564(2) 0.35096(17) 0.0289(8) Uani 1 d . . .
C11 C 0.6164(10) 0.6354(2) 0.3431(2) 0.0343(8) Uani 1 d . . .
H11 H 0.6472 0.6584 0.2950 0.041 Uiso 1 calc . . R
C12 C 0.7189(10) 0.6808(2) 0.4043(2) 0.0370(9) Uani 1 d . . .
H12 H 0.8149 0.7353 0.3984 0.044 Uiso 1 calc . . R
C13 C 0.6815(10) 0.6467(2) 0.4748(2) 0.0375(9) Uani 1 d . . .
H13 H 0.7538 0.6779 0.5170 0.045 Uiso 1 calc . . R
C14 C 0.5405(10) 0.5681(2) 0.48376(19) 0.0334(8) Uani 1 d . . .
H14 H 0.5198 0.5450 0.5321 0.040 Uiso 1 calc . . R
Li1 Li 0.0426(19) 0.3099(4) 0.5368(3) 0.0424(15) Uani 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 C1 1.253(4) . ?
O2 H2 0.9741 . ?
O2 C3 1.344(4) . ?
O3 C6 1.289(4) . ?
O4 C7 1.245(4) . ?
O5 H5A 0.9452 . ?
O5 H5B 0.9437 . ?
C1 C2 1.448(5) . ?
C1 C10 1.467(5) . ?
C2 C3 1.395(5) . ?
C2 C8 1.446(4) . ?
C3 C4 1.408(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.360(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.446(5) . ?
C6 C8 1.426(5) . ?
C7 C8 1.438(5) . ?
C7 C9 1.492(5) . ?
C9 C10 1.414(4) . ?
C9 C14 1.395(5) . ?
C10 C11 1.389(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(5) . ?
C14 H14 0.9500 . ?

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
C3 O2 H2 104.8 . . ?
H5A O5 H5B 109.5 . . ?
O1 C1 C2 121.2(3) . . ?
O1 C1 C10 119.8(3) . . ?
C2 C1 C10 119.0(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 C8 120.2(3) . . ?
C8 C2 C1 121.6(3) . . ?
O2 C3 C2 122.9(3) . . ?
O2 C3 C4 116.9(3) . . ?
C2 C3 C4 120.2(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.3(3) . . ?
C6 C5 H5 118.8 . . ?
O3 C6 C5 117.3(3) . . ?
O3 C6 C8 125.3(3) . . ?
C8 C6 C5 117.4(3) . . ?
O4 C7 C8 124.4(3) . . ?
O4 C7 C9 117.3(3) . . ?
C8 C7 C9 118.2(3) . . ?
C6 C8 C2 119.3(3) . . ?
C6 C8 C7 121.0(3) . . ?
C7 C8 C2 119.7(3) . . ?
C10 C9 C7 121.7(3) . . ?
C14 C9 C7 119.6(3) . . ?
C14 C9 C10 118.7(3) . . ?
C9 C10 C1 119.4(3) . . ?
C11 C10 C1 121.0(3) . . ?
C11 C10 C9 119.5(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.8(3) . . ?
C13 C14 H14 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -1.2(5) . . . . ?
O1 C1 C2 C8 177.9(3) . . . . ?
O1 C1 C10 C9 -177.3(3) . . . . ?
O1 C1 C10 C11 4.0(5) . . . . ?
O2 C3 C4 C5 178.8(3) . . . . ?
O3 C6 C8 C2 -177.0(3) . . . . ?
O3 C6 C8 C7 3.8(5) . . . . ?
O4 C7 C8 C2 -173.7(3) . . . . ?
O4 C7 C8 C6 5.5(5) . . . . ?
O4 C7 C9 C10 174.3(3) . . . . ?
O4 C7 C9 C14 -5.6(5) . . . . ?
C1 C2 C3 O2 1.6(5) . . . . ?
C1 C2 C3 C4 -178.9(3) . . . . ?
C1 C2 C8 C6 178.5(3) . . . . ?
C1 C2 C8 C7 -2.2(5) . . . . ?
C1 C10 C11 C12 177.8(3) . . . . ?
C2 C1 C10 C9 3.5(5) . . . . ?
C2 C1 C10 C11 -175.2(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C2 C8 C6 -2.3(5) . . . . ?
C3 C2 C8 C7 176.9(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 O3 178.3(3) . . . . ?
C4 C5 C6 C8 -0.3(5) . . . . ?
C5 C6 C8 C2 1.5(5) . . . . ?
C5 C6 C8 C7 -177.7(3) . . . . ?
C7 C9 C10 C1 0.8(5) . . . . ?
C7 C9 C10 C11 179.5(3) . . . . ?
C7 C9 C14 C13 -178.6(3) . . . . ?
C8 C2 C3 O2 -177.6(3) . . . . ?
C8 C2 C3 C4 1.9(5) . . . . ?
C8 C7 C9 C10 -5.8(5) . . . . ?
C8 C7 C9 C14 174.3(3) . . . . ?
C9 C7 C8 C2 6.4(5) . . . . ?
C9 C7 C8 C6 -174.4(3) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C10 C1 C2 C3 178.0(3) . . . . ?
C10 C1 C2 C8 -2.8(5) . . . . ?
C10 C9 C14 C13 1.5(5) . . . . ?
C10 C11 C12 C13 1.4(6) . . . . ?
C11 C12 C13 C14 -0.5(6) . . . . ?
C12 C13 C14 C9 -1.0(6) . . . . ?
C14 C9 C10 C1 -179.3(3) . . . . ?
C14 C9 C10 C11 -0.6(5) . . . . ?

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 -7 0.0147 -0.0009 -8.0096 -6.9854 -0.2969 -0.2720 -0.8884
0 8 7 0.0147 0.0009 8.0096 6.9854 0.2969 0.2720 0.8884
-2 1 -1 0.4266 -1.9965 0.9952 -1.0052 -0.5842 -0.4505 0.3579
2 -1 1 0.3526 1.9965 -0.9952 1.0052 0.5842 0.4505 -0.3579
0 7 -9 0.0010 0.0092 7.0179 -8.9915 -0.7206 0.7219 0.0906
0 -7 9 0.0229 -0.0092 -7.0179 8.9915 0.7206 -0.7219 -0.0906

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(4)
2 0.1(4)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2013ncs0810
_database_code_depnum_ccdc_archive 'CCDC 1419043'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        '1,4-dihydroxyanthraquinone lithium hydrate'
_chemical_formula_moiety         'C14 H7.4 Li O4.2'
_chemical_formula_sum            'C14 H7.50 Li O4.25'
_chemical_formula_weight         250.64
_chemical_absolute_configuration unk
_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 0.0030 0.0020 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   3.6746(2)
_cell_length_b                   16.1112(11)
_cell_length_c                   18.1111(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1072.22(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0.0
_cell_measurement_theta_max      0.0
_cell_measurement_temperature    293.15
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'blackish red'
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             514
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.1279
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5632
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.25
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'fine-focus sealed tube'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                982
_reflns_number_total             2266
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1969
_refine_ls_R_factor_gt           0.0829
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0892P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1803
_refine_ls_wR_factor_ref         0.2168
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 3.08928 -2.08928
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Others
 Fixed Sof: O5(0.2) H5A(0.2) H5B(0.2)
 Fixed k1: basf(-2.08928)
4.a Riding coordinates:
 O2(H2), O5(H5A,H5B)
4.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C12(H12), C4(H4), C14(H14), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O4 O 0.2676(17) 0.4008(2) 0.4998(2) 0.0789(18) Uani 1 d . . .
O3 O 0.0335(16) 0.2606(2) 0.4352(2) 0.0845(18) Uani 1 d . . .
O1 O 0.3541(14) 0.5497(2) 0.2333(2) 0.0682(15) Uani 1 d . . .
O2 O 0.0881(16) 0.4237(2) 0.17015(18) 0.0711(16) Uani 1 d . . .
H2 H 0.2623 0.4554 0.1676 0.107 Uiso 1 d . . R
C10 C 0.4608(17) 0.5553(3) 0.3610(3) 0.0396(14) Uani 1 d . . .
C2 C 0.2019(17) 0.4287(3) 0.3009(3) 0.0404(15) Uani 1 d . . .
C9 C 0.4508(18) 0.5154(3) 0.4291(3) 0.0403(15) Uani 1 d . . .
C8 C 0.1864(18) 0.3862(3) 0.3706(3) 0.0389(15) Uani 1 d . . .
C7 C 0.2963(18) 0.4297(3) 0.4365(3) 0.0473(17) Uani 1 d . . .
C1 C 0.3381(17) 0.5133(3) 0.2945(3) 0.0433(16) Uani 1 d . . .
C6 C 0.049(2) 0.3055(3) 0.3747(3) 0.0552(19) Uani 1 d . . .
C11 C 0.6014(18) 0.6357(3) 0.3574(3) 0.0527(18) Uani 1 d . . .
H11 H 0.6178 0.6626 0.3121 0.063 Uiso 1 calc . . R
C5 C -0.066(2) 0.2676(3) 0.3073(3) 0.0563(19) Uani 1 d . . .
H5 H -0.1487 0.2130 0.3083 0.068 Uiso 1 calc . . R
C12 C 0.716(2) 0.6755(4) 0.4210(4) 0.066(2) Uani 1 d . . .
H12 H 0.8071 0.7293 0.4184 0.079 Uiso 1 calc . . R
C4 C -0.060(2) 0.3087(3) 0.2419(3) 0.0529(18) Uani 1 d . . .
H4 H -0.1497 0.2831 0.1996 0.063 Uiso 1 calc . . R
C14 C 0.5685(19) 0.5568(4) 0.4924(3) 0.0583(19) Uani 1 d . . .
H14 H 0.5596 0.5303 0.5380 0.070 Uiso 1 calc . . R
C3 C 0.0795(18) 0.3883(3) 0.2372(3) 0.0436(17) Uani 1 d . . .
C13 C 0.696(2) 0.6358(5) 0.4874(4) 0.067(2) Uani 1 d . . .
H13 H 0.7712 0.6632 0.5299 0.080 Uiso 1 calc . . R
Li1 Li 0.079(4) 0.2987(6) 0.5332(6) 0.078(4) Uani 1 d . . .
O5 O -0.140(7) 0.3660(12) 0.6059(9) 0.068(7) Uani 0.20 d . . .
H5A H -0.0319 0.4232 0.6191 0.103 Uiso 0.20 d . . R
H5B H -0.4036 0.3854 0.6004 0.103 Uiso 0.20 d . . R


_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
O4 C7 1.242(6) . ?
O3 C6 1.314(6) . ?
O1 C1 1.255(6) . ?
O2 H2 0.8201 . ?
O2 C3 1.341(6) . ?
C10 C9 1.391(7) . ?
C10 C1 1.454(7) . ?
C10 C11 1.395(7) . ?
C2 C8 1.438(7) . ?
C2 C1 1.456(7) . ?
C2 C3 1.400(7) . ?
C9 C7 1.499(7) . ?
C9 C14 1.396(7) . ?
C8 C7 1.442(7) . ?
C8 C6 1.396(7) . ?
C6 C5 1.430(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(9) . ?
C5 H5 0.9300 . ?
C5 C4 1.358(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(9) . ?
C4 H4 0.9300 . ?
C4 C3 1.383(8) . ?
C14 H14 0.9300 . ?
C14 C13 1.360(10) . ?
C13 H13 0.9300 . ?
O5 H5A 1.0318 . ?
O5 H5B 1.0227 . ?

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
C3 O2 H2 109.5 . . ?
C9 C10 C1 120.6(5) . . ?
C9 C10 C11 118.7(5) . . ?
C11 C10 C1 120.6(5) . . ?
C8 C2 C1 122.0(5) . . ?
C3 C2 C8 119.4(5) . . ?
C3 C2 C1 118.7(5) . . ?
C10 C9 C7 121.1(5) . . ?
C10 C9 C14 119.9(5) . . ?
C14 C9 C7 118.9(5) . . ?
C2 C8 C7 119.0(4) . . ?
C6 C8 C2 120.3(5) . . ?
C6 C8 C7 120.7(5) . . ?
O4 C7 C9 117.4(5) . . ?
O4 C7 C8 124.0(5) . . ?
C8 C7 C9 118.6(5) . . ?
O1 C1 C10 119.9(5) . . ?
O1 C1 C2 121.6(5) . . ?
C10 C1 C2 118.5(5) . . ?
O3 C6 C8 124.9(5) . . ?
O3 C6 C5 117.6(5) . . ?
C8 C6 C5 117.4(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(6) . . ?
C12 C11 H11 119.9 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.0(5) . . ?
C4 C5 H5 119.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(6) . . ?
C13 C12 H12 120.0 . . ?
C5 C4 H4 119.6 . . ?
C5 C4 C3 120.9(5) . . ?
C3 C4 H4 119.6 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.0(6) . . ?
C13 C14 H14 120.0 . . ?
O2 C3 C2 122.8(5) . . ?
O2 C3 C4 117.3(5) . . ?
C4 C3 C2 119.9(5) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.1(6) . . ?
C14 C13 H13 119.5 . . ?
H5A O5 H5B 96.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C6 C5 C4 -179.8(7) . . . . ?
C10 C9 C7 O4 -173.9(6) . . . . ?
C10 C9 C7 C8 5.3(8) . . . . ?
C10 C9 C14 C13 -0.7(10) . . . . ?
C10 C11 C12 C13 0.7(11) . . . . ?
C2 C8 C7 O4 174.4(6) . . . . ?
C2 C8 C7 C9 -4.8(8) . . . . ?
C2 C8 C6 O3 177.9(6) . . . . ?
C2 C8 C6 C5 1.1(9) . . . . ?
C9 C10 C1 O1 -178.9(6) . . . . ?
C9 C10 C1 C2 0.5(8) . . . . ?
C9 C10 C11 C12 -2.2(9) . . . . ?
C9 C14 C13 C12 -0.8(11) . . . . ?
C8 C2 C1 O1 179.3(6) . . . . ?
C8 C2 C1 C10 -0.1(8) . . . . ?
C8 C2 C3 O2 -179.5(6) . . . . ?
C8 C2 C3 C4 0.9(9) . . . . ?
C8 C6 C5 C4 -2.8(11) . . . . ?
C7 C9 C14 C13 -177.4(7) . . . . ?
C7 C8 C6 O3 -5.4(11) . . . . ?
C7 C8 C6 C5 177.8(6) . . . . ?
C1 C10 C9 C7 -3.1(9) . . . . ?
C1 C10 C9 C14 -179.8(6) . . . . ?
C1 C10 C11 C12 179.7(7) . . . . ?
C1 C2 C8 C7 2.3(8) . . . . ?
C1 C2 C8 C6 179.1(6) . . . . ?
C1 C2 C3 O2 1.2(9) . . . . ?
C1 C2 C3 C4 -178.4(6) . . . . ?
C6 C8 C7 O4 -2.3(10) . . . . ?
C6 C8 C7 C9 178.5(6) . . . . ?
C6 C5 C4 C3 3.6(11) . . . . ?
C11 C10 C9 C7 178.8(6) . . . . ?
C11 C10 C9 C14 2.1(9) . . . . ?
C11 C10 C1 O1 -0.8(9) . . . . ?
C11 C10 C1 C2 178.5(6) . . . . ?
C11 C12 C13 C14 0.8(12) . . . . ?
C5 C4 C3 O2 177.8(7) . . . . ?
C5 C4 C3 C2 -2.6(10) . . . . ?
C14 C9 C7 O4 2.8(9) . . . . ?
C14 C9 C7 C8 -178.0(6) . . . . ?
C3 C2 C8 C7 -177.0(6) . . . . ?
C3 C2 C8 C6 -0.2(9) . . . . ?
C3 C2 C1 O1 -1.4(9) . . . . ?
C3 C2 C1 C10 179.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 3.08928
2 -2.08928

_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6_Li-14hnaq_120K
_database_code_depnum_ccdc_archive 'CCDC 1419044'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        'Lithium 1-hydroxy-4-nitroanthraquinone'
_chemical_formula_moiety         'C14 H8 Li N O6'
_chemical_formula_sum            'C14 H8 Li N O6'
_chemical_formula_weight         293.16
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'Li C14 O6 N H8'
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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
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

_symmetry_Int_Tables_number      19
_cell_length_a                   4.8535(3)
_cell_length_b                   13.0952(10)
_cell_length_c                   18.9644(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1205.33(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1526
_cell_measurement_temperature    120
_cell_measurement_theta_max      61.1950
_cell_measurement_theta_min      4.1025
_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
_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_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      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -110.00  -62.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -      -31.9956  178.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega -110.00  -81.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -      -31.9956 -178.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega   57.00   87.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -       31.9956   57.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega   -6.00   52.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -       31.9956  -57.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega -133.00 -105.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -      -75.0000 -111.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega   19.00   61.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  -30.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  7 omega   97.00  124.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  111.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   53.00   84.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  -94.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
  9 omega   17.00   49.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  -94.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
 10 omega   22.00  110.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  -61.0000   30.0000 88

#__ type_ start__ end____ width___ exp.time_
 11 omega   45.00   77.00   1.0000  186.5600
omega____ theta____ kappa____ phi______ frames
    -       89.8409  -94.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega   10.00  101.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -       31.9956   57.0000 -150.0000 91

#__ type_ start__ end____ width___ exp.time_
 13 omega    5.00  105.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -       31.9956   37.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 14 omega   10.00  101.00   1.0000    5.3400
omega____ theta____ kappa____ phi______ frames
    -       31.9956   57.0000  -30.0000 91

#__ type_ start__ end____ width___ exp.time_
 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_source                   'Enhance Ultra (Cu) X-ray Source'
_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_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_reflns_threshold_expression     I>=2u(I)
_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)'
_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_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.0713
_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
_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)
;
_atom_sites_solution_primary     direct
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_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_
_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
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_
_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

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.2(3)
2 -0.2(3)

_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2013ncs0809
_database_code_depnum_ccdc_archive 'CCDC 1419045'

_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             13-12-03
_audit_creation_method           
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_chemical_name_systematic        'Lithium 1-Hydroxy-4-nitroanthraquinone'
_chemical_formula_moiety         'C14 H8 Li N O6'
_chemical_formula_sum            'C14 H8 Li N O6'
_chemical_formula_weight         293.16
_chemical_absolute_configuration ad
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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
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

_symmetry_Int_Tables_number      19
_cell_length_a                   4.8953(4)
_cell_length_b                   13.2668(10)
_cell_length_c                   19.1081(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1240.97(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293.15
_cell_measurement_reflns_used    6750
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      27.5
_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
_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
_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
_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)
_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)'
_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_R_factor_all          0.1606
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      1.0796
_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
_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)
;
_atom_sites_solution_primary     direct
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_
_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 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_
_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
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 . ?
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 2.5(12)
2 -1.5(12)

_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_st237_cu_st_re_abs2
_database_code_depnum_ccdc_archive 'CCDC 1419046'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        '1,5-dihydroxyanthraquinone lithium salt'
_chemical_formula_moiety         '2(C7 H7 Li O4), H2 O'
_chemical_formula_sum            'C14 H16 Li2 O9'
_chemical_formula_weight         342.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H16 Li2 O9'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0010 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.0112(2)
_cell_length_b                   7.5031(4)
_cell_length_c                   21.0358(8)
_cell_angle_alpha                97.619(4)
_cell_angle_beta                 91.892(4)
_cell_angle_gamma                108.338(5)
_cell_volume                     741.79(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6099
_cell_measurement_temperature    121(3)
_cell_measurement_theta_max      62.8550
_cell_measurement_theta_min      4.2460
_exptl_absorpt_coefficient_mu    1.083
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.877
_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            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.4764
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.0183
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14922
_diffrn_reflns_theta_full        63.05
_diffrn_reflns_theta_max         63.05
_diffrn_reflns_theta_min         4.25
_diffrn_ambient_temperature      121(3)
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00  -17.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -      -34.0930  124.0000  -36.0000 73

#__ type_ start__ end____ width___ exp.time_
  2 omega   38.00  102.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.0930   57.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega   38.00  107.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.0930  178.0000  -90.0000 69

#__ type_ start__ end____ width___ exp.time_
  4 omega   14.00   96.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.0930   57.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega  -31.00   49.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.0930  -37.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega   25.00  126.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -91.0000  -97.6489 101

#__ type_ start__ end____ width___ exp.time_
  7 omega   74.00  101.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  128.6218 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   20.00   47.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000   36.9144 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   18.00   44.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -17.0000  -18.3117 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   20.00  111.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -84.0000   62.1541 91

#__ type_ start__ end____ width___ exp.time_
 11 omega   56.00  109.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -17.0000  -18.3117 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   54.00  101.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   22.0000   -1.0367 47

#__ type_ start__ end____ width___ exp.time_
 13 omega  108.00  159.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   22.0000   -1.0367 51

#__ type_ start__ end____ width___ exp.time_
 14 omega   59.00  121.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
 15 omega   21.00   47.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  128.6218 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   42.00   89.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
 17 omega   21.00   68.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 18 omega   71.00   97.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000   97.6845 26

#__ type_ start__ end____ width___ exp.time_
 19 omega  111.00  137.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   26.00   74.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
 21 omega   33.00   76.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
 22 omega   18.00   66.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   18.00  123.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000    0.0000  150.0000 105

#__ type_ start__ end____ width___ exp.time_
 24 omega  133.00  159.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000    0.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   25.00   74.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 26 omega   23.00   60.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 27 omega   42.00   79.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 28 omega   20.00   55.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
 29 omega   76.00  101.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 30 omega   27.00   54.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 31 omega   23.00   51.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 32 omega   24.00   49.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 33 omega   19.00   44.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -15.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 34 omega  112.00  143.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -15.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 35 omega   29.00   54.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000   97.6845 25

#__ type_ start__ end____ width___ exp.time_
 36 omega   29.00   55.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   75.00  105.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000   36.9144 30

#__ type_ start__ end____ width___ exp.time_
 38 omega  137.00  162.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 39 omega   42.00   98.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  -24.9581 56

#__ type_ start__ end____ width___ exp.time_
 40 omega   98.00  123.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 41 omega   71.00  100.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000 -136.7190 29

#__ type_ start__ end____ width___ exp.time_
 42 omega  -54.00   35.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -      -34.0930   57.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
 43 omega -110.00  -57.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -      -34.0930 -178.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 44 omega    4.00  104.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.0930   77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 45 omega   14.00  103.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.0930   57.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 46 omega   14.00  103.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.0930   57.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
 47 omega   35.00  110.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.0930  178.0000  150.0000 75

#__ type_ start__ end____ width___ exp.time_
 48 omega    4.00  104.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.0930   77.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
 49 omega -134.00  -34.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 50 omega -134.00  -34.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
 51 omega -134.00  -34.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 52 omega -134.00  -35.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -76.0000   77.3344 99

#__ type_ start__ end____ width___ exp.time_
 53 omega -134.00  -34.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
 54 omega   60.00  161.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -150.0000 101

#__ type_ start__ end____ width___ exp.time_
 55 omega   60.00  161.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   90.0000 101

#__ type_ start__ end____ width___ exp.time_
 56 omega   60.00  137.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
 57 omega   60.00  161.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 58 omega   60.00  161.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
 59 omega   60.00  161.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
 60 omega   67.00  162.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
 61 omega   60.00  161.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
 62 omega   60.00  161.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
 63 omega   60.00  161.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 64 omega   60.00  161.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -90.0000 101

#__ type_ start__ end____ width___ exp.time_
 65 omega   61.00  163.00   1.0000    8.6300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000 -150.0000 102
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.3044655000
_diffrn_orient_matrix_UB_12      -0.0349541000
_diffrn_orient_matrix_UB_13      0.0190334000
_diffrn_orient_matrix_UB_21      -0.1102161000
_diffrn_orient_matrix_UB_22      -0.0609734000
_diffrn_orient_matrix_UB_23      -0.0713845000
_diffrn_orient_matrix_UB_31      -0.0266829000
_diffrn_orient_matrix_UB_32      -0.2072117000
_diffrn_orient_matrix_UB_33      0.0059994000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2115
_reflns_number_total             2377
_reflns_odcompleteness_completeness 97.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_reflns_threshold_expression     >2sigma(I)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0603P)²+0.2080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1022
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O3(H3A,H3B), O4(H4A,H4B), O7(H7A,H7B), O8(H8A,H8B), O9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.0565(2) 0.71681(16) 0.17659(5) 0.0235(3) Uani 1 d . . .
O2 O 0.2610(2) 0.45929(16) 0.10904(5) 0.0233(3) Uani 1 d . . .
O3 O 0.6266(2) 0.66597(17) 0.25193(5) 0.0250(3) Uani 1 d . . .
H3A H 0.7790 0.6780 0.2255 0.037 Uiso 1 d . . R
H3B H 0.6480 0.5780 0.2775 0.037 Uiso 1 d . . R
O4 O 0.0509(2) 0.36362(17) 0.24028(5) 0.0273(3) Uani 1 d . . .
H4A H -0.0440 0.3871 0.2771 0.041 Uiso 1 d . . R
H4B H 0.1160 0.2591 0.2451 0.041 Uiso 1 d . . R
O5 O 0.2838(2) 0.58198(16) 0.66985(5) 0.0245(3) Uani 1 d . . .
O6 O 0.2888(2) 0.22885(16) 0.39660(5) 0.0241(3) Uani 1 d . . .
O7 O 0.7164(2) 0.00478(17) 0.33964(6) 0.0299(3) Uani 1 d . . .
H7A H 0.8980 0.0601 0.3562 0.045 Uiso 1 d . . R
H7B H 0.6990 -0.1059 0.3128 0.045 Uiso 1 d . . R
O8 O 0.2925(2) 0.07426(17) 0.24136(5) 0.0283(3) Uani 1 d . . .
H8A H 0.4051 0.1271 0.2087 0.042 Uiso 1 d . . R
H8B H 0.2021 -0.0529 0.2237 0.042 Uiso 1 d . . R
O9 O -0.4130(3) 0.24373(18) 0.14965(6) 0.0313(3) Uani 1 d . . .
H9A H -0.2309 0.3090 0.1717 0.047 Uiso 1 d . . R
H9B H -0.4939 0.3290 0.1332 0.047 Uiso 1 d . . R
C1 C -0.0404(3) 0.7315(2) 0.11920(7) 0.0210(4) Uani 1 d . . .
C2 C -0.0171(3) 0.6168(2) 0.06102(7) 0.0189(3) Uani 1 d . . .
C3 C 0.1332(3) 0.4793(2) 0.05983(7) 0.0197(3) Uani 1 d . . .
C4 C 0.1406(3) 0.3595(2) -0.00198(7) 0.0199(4) Uani 1 d . . .
C5 C -0.1814(3) 0.8664(2) 0.11490(8) 0.0236(4) Uani 1 d . . .
H5 H -0.1996 0.9435 0.1531 0.028 Uiso 1 calc . . R
C6 C -0.2924(3) 0.8890(2) 0.05733(8) 0.0257(4) Uani 1 d . . .
H6 H -0.3831 0.9823 0.0560 0.031 Uiso 1 calc . . R
C7 C -0.2729(3) 0.7756(2) 0.00063(8) 0.0238(4) Uani 1 d . . .
H7 H -0.3513 0.7917 -0.0391 0.029 Uiso 1 calc . . R
C8 C 0.1914(3) 0.4727(2) 0.61449(7) 0.0211(4) Uani 1 d . . .
C9 C -0.0722(3) 0.3264(2) 0.61016(8) 0.0234(4) Uani 1 d . . .
H9 H -0.1778 0.3138 0.6469 0.028 Uiso 1 calc . . R
C10 C -0.1788(3) 0.2028(2) 0.55450(8) 0.0238(4) Uani 1 d . . .
H10 H -0.3579 0.1080 0.5529 0.029 Uiso 1 calc . . R
C11 C -0.0261(3) 0.2156(2) 0.50026(7) 0.0218(4) Uani 1 d . . .
H11 H -0.0989 0.1272 0.4622 0.026 Uiso 1 calc . . R
C12 C 0.2316(3) 0.3566(2) 0.50159(7) 0.0196(3) Uani 1 d . . .
C13 C 0.3886(3) 0.3596(2) 0.44267(7) 0.0197(4) Uani 1 d . . .
C14 C 0.6557(3) 0.5100(2) 0.44172(7) 0.0193(3) Uani 1 d . . .
Li1 Li 0.2714(6) 0.5678(4) 0.19737(13) 0.0264(6) Uani 1 d . . .
Li2 Li 0.4914(6) 0.1627(4) 0.32503(13) 0.0273(6) Uani 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 C1 1.3176(19) . ?
O1 Li1 1.859(3) . ?
O2 C3 1.2496(19) . ?
O3 H3A 0.9479 . ?
O3 H3B 0.9334 . ?
O4 H4A 0.9472 . ?
O4 H4B 0.9550 . ?
O5 C8 1.3096(19) . ?
O6 C13 1.2486(19) . ?
O7 H7A 0.9082 . ?
O7 H7B 0.9181 . ?
O8 H8A 0.9509 . ?
O8 H8B 0.9363 . ?
O9 H9A 0.9582 . ?
O9 H9B 0.9517 . ?
C1 C2 1.430(2) . ?
C1 C5 1.415(2) . ?
C2 C3 1.455(2) . ?
C2 C4 1.426(2) 2_565 ?
C3 C4 1.488(2) . ?
C4 C2 1.426(2) 2_565 ?
C4 C7 1.378(2) 2_565 ?
C5 H5 0.9500 . ?
C5 C6 1.369(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(2) . ?
C7 C4 1.378(2) 2_565 ?
C7 H7 0.9500 . ?
C8 C9 1.418(2) . ?
C8 C14 1.428(2) 2_666 ?
C9 H9 0.9500 . ?
C9 C10 1.370(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(2) . ?
C12 C13 1.489(2) . ?
C12 C14 1.423(2) 2_666 ?
C13 C14 1.457(2) . ?
C14 C8 1.428(2) 2_666 ?
C14 C12 1.423(2) 2_666 ?

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
C1 O1 Li1 128.29(13) . . ?
H3A O3 H3B 102.3 . . ?
H4A O4 H4B 108.0 . . ?
H7A O7 H7B 109.9 . . ?
H8A O8 H8B 104.5 . . ?
H9A O9 H9B 111.8 . . ?
O1 C1 C2 124.06(15) . . ?
O1 C1 C5 118.06(14) . . ?
C5 C1 C2 117.87(14) . . ?
C1 C2 C3 122.21(14) . . ?
C4 C2 C1 118.96(15) 2_565 . ?
C4 C2 C3 118.82(14) 2_565 . ?
O2 C3 C2 122.25(14) . . ?
O2 C3 C4 118.30(14) . . ?
C2 C3 C4 119.44(14) . . ?
C2 C4 C3 121.65(15) 2_565 . ?
C7 C4 C2 120.59(15) 2_565 2_565 ?
C7 C4 C3 117.76(14) 2_565 . ?
C1 C5 H5 119.1 . . ?
C6 C5 C1 121.90(15) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.31(15) . . ?
C7 C6 H6 119.8 . . ?
C4 C7 C6 120.33(15) 2_565 . ?
C4 C7 H7 119.8 2_565 . ?
C6 C7 H7 119.8 . . ?
O5 C8 C9 118.48(14) . . ?
O5 C8 C14 123.59(14) . 2_666 ?
C9 C8 C14 117.92(14) . 2_666 ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 121.91(15) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.29(15) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.27(15) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 117.74(14) . . ?
C11 C12 C14 120.65(15) . 2_666 ?
C14 C12 C13 121.59(14) 2_666 . ?
O6 C13 C12 118.20(14) . . ?
O6 C13 C14 122.65(14) . . ?
C14 C13 C12 119.11(14) . . ?
C8 C14 C13 121.89(14) 2_666 . ?
C12 C14 C8 118.92(14) 2_666 2_666 ?
C12 C14 C13 119.19(14) 2_666 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -3.8(2) . . . . ?
O1 C1 C2 C4 177.43(14) . . . 2_565 ?
O1 C1 C5 C6 -178.99(15) . . . . ?
O2 C3 C4 C2 -175.52(14) . . . 2_565 ?
O2 C3 C4 C7 4.1(2) . . . 2_565 ?
O5 C8 C9 C10 -177.99(15) . . . . ?
O6 C13 C14 C8 5.9(2) . . . 2_666 ?
O6 C13 C14 C12 -173.94(14) . . . 2_666 ?
C1 C2 C3 O2 -3.2(2) . . . . ?
C1 C2 C3 C4 177.80(14) . . . . ?
C1 C5 C6 C7 1.1(3) . . . . ?
C2 C1 C5 C6 -0.3(2) . . . . ?
C2 C3 C4 C2 3.5(2) . . . 2_565 ?
C2 C3 C4 C7 -176.82(14) . . . 2_565 ?
C4 C2 C3 O2 175.58(14) 2_565 . . . ?
C4 C2 C3 C4 -3.4(2) 2_565 . . . ?
C5 C1 C2 C3 177.54(14) . . . . ?
C5 C1 C2 C4 -1.2(2) . . . 2_565 ?
C5 C6 C7 C4 -0.3(3) . . . 2_565 ?
C8 C9 C10 C11 1.3(3) . . . . ?
C9 C10 C11 C12 -1.8(2) . . . . ?
C10 C11 C12 C13 178.36(14) . . . . ?
C10 C11 C12 C14 0.2(2) . . . 2_666 ?
C11 C12 C13 O6 -4.2(2) . . . . ?
C11 C12 C13 C14 177.90(14) . . . . ?
C12 C13 C14 C8 -176.36(13) . . . 2_666 ?
C12 C13 C14 C12 3.8(2) . . . 2_666 ?
C14 C8 C9 C10 0.7(2) 2_666 . . . ?
C14 C12 C13 O6 173.94(14) 2_666 . . . ?
C14 C12 C13 C14 -3.9(2) 2_666 . . . ?
Li1 O1 C1 C2 6.3(2) . . . . ?
Li1 O1 C1 C5 -175.07(15) . . . . ?

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 -5 3 0.0420 -0.0028 -4.9864 3.0101 0.2324 0.0895 1.0514
0 5 -3 0.0560 0.0028 4.9864 -3.0101 -0.2324 -0.0895 -1.0514
3 -1 0 0.2316 2.9933 -0.9971 0.0274 -0.8760 -0.2711 0.1269
-3 1 0 0.2316 -2.9933 0.9971 -0.0274 0.8760 0.2711 -0.1269
0 0 -13 0.0057 0.0119 -0.0006 -12.9604 -0.2503 0.9239 -0.0779
0 0 13 0.0127 -0.0119 0.0006 12.9604 0.2503 -0.9239 0.0779

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_description       plate
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_st298-b-cu-120k_abs
_database_code_depnum_ccdc_archive 'CCDC 1419047'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        1-Hyrdoxy-4-nitiroanthraquinone
_chemical_formula_moiety         'C14 H7 N O5'
_chemical_formula_sum            'C14 H7 N O5'
_chemical_formula_weight         269.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 O5 N H5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3423(2)
_cell_length_b                   10.0879(2)
_cell_length_c                   14.4961(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 89.137(2)
_cell_angle_gamma                90.00
_cell_volume                     1073.58(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12235
_cell_measurement_temperature    120
_cell_measurement_theta_max      71.1520
_cell_measurement_theta_min      5.3160
_exptl_absorpt_coefficient_mu    1.101
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.738
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.4737
_exptl_crystal_size_mid          0.1084
_exptl_crystal_size_min          0.0722
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23531
_diffrn_reflns_theta_full        71.21
_diffrn_reflns_theta_max         71.21
_diffrn_reflns_theta_min         5.34
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -4.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -69.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -85.00  -26.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  125.0000    0.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega    8.00  120.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   19.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
  6 omega  128.00  173.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   25.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega   92.00  177.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   63.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   71.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega   70.00  101.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   66.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   90.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
 12 omega   43.00   76.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00   72.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 14 omega   36.00   61.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   32.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
 16 omega  -22.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 91

#__ type_ start__ end____ width___ exp.time_
 17 omega -125.00  -77.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -54.7500 -153.0000  132.0000 48

#__ type_ start__ end____ width___ exp.time_
 18 omega   23.00  126.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000    0.0000 103

#__ type_ start__ end____ width___ exp.time_
 19 omega   23.00  126.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
 20 omega   23.00  126.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000   90.0000 103

#__ type_ start__ end____ width___ exp.time_
 21 omega -148.00 -100.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -91.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
 22 omega   39.00   83.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
 23 omega   37.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   12.0000   90.0000 141

#__ type_ start__ end____ width___ exp.time_
 24 omega   37.00  149.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
 25 omega   39.00   83.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000  150.0000 44

#__ type_ start__ end____ width___ exp.time_
 26 omega   35.00   72.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 27 omega   82.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   37.0000  150.0000 96

#__ type_ start__ end____ width___ exp.time_
 28 omega   86.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   50.0000 -120.0000 92

#__ type_ start__ end____ width___ exp.time_
 29 omega  -27.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
 30 omega  -25.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
 31 omega -125.00  -77.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -54.7500 -153.0000 -173.0000 48

#__ type_ start__ end____ width___ exp.time_
 32 omega -126.00  -23.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -77.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
 33 omega   33.00  124.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   57.0000   60.0000 91

#__ type_ start__ end____ width___ exp.time_
 34 omega  -18.00   85.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500  -99.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
 35 omega -146.00  -43.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 36 omega -145.00  -46.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -73.0000 -108.8823 99

#__ type_ start__ end____ width___ exp.time_
 37 omega -146.00  -43.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
 38 omega   37.00   71.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
 39 omega   78.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 40 omega   85.00  177.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   63.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
 41 omega   78.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
 42 omega   78.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
 43 omega   32.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
 44 omega  -69.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
 45 omega -122.00  -29.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  141.0000  -88.0000 93

#__ type_ start__ end____ width___ exp.time_
 46 omega   23.00  126.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 47 omega   73.00  127.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500  125.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
 48 omega   23.00  126.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 49 omega -146.00  -43.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 50 omega -146.00  -42.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -79.0000   86.4654 104

#__ type_ start__ end____ width___ exp.time_
 51 omega   78.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
 52 omega   35.00   72.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 53 omega   37.00  149.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
 54 omega   37.00  149.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000 -180.0000 112

#__ type_ start__ end____ width___ exp.time_
 55 omega   78.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 56 omega   78.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  150.0000 100

#__ type_ start__ end____ width___ exp.time_
 57 omega  -73.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
 58 omega  -71.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 59 omega   23.00  126.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000  -60.0000 103

#__ type_ start__ end____ width___ exp.time_
 60 omega   23.00  126.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
 61 omega   23.00  126.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
 62 omega   23.00  126.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000 -120.0000 103

#__ type_ start__ end____ width___ exp.time_
 63 omega -146.00  -43.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 64 omega -146.00  -43.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -77.0000  -60.0000 103

#__ type_ start__ end____ width___ exp.time_
 65 omega -146.00  -42.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -79.0000  111.0374 104

#__ type_ start__ end____ width___ exp.time_
 66 omega   78.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
 67 omega   78.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 68 omega   78.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   60.0000 100

#__ type_ start__ end____ width___ exp.time_
 69 omega   78.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
 70 omega   85.00  177.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      109.5000   63.0000 -150.0000 92
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0144582000
_diffrn_orient_matrix_UB_12      -0.1347774000
_diffrn_orient_matrix_UB_13      0.0493371000
_diffrn_orient_matrix_UB_21      -0.0189044000
_diffrn_orient_matrix_UB_22      0.0700905000
_diffrn_orient_matrix_UB_23      0.0940754000
_diffrn_orient_matrix_UB_31      -0.2084915000
_diffrn_orient_matrix_UB_32      -0.0156101000
_diffrn_orient_matrix_UB_33      -0.0035112000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1876
_reflns_number_total             2061
_reflns_odcompleteness_completeness 93.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2061
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0964P)²+0.2599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1398
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.23723(15) 0.94194(10) 0.78852(6) 0.0279(3) Uani 1 d . . .
O2 O 0.53108(15) 0.92530(10) 0.78713(7) 0.0306(3) Uani 1 d . . .
O3 O 0.32134(16) 1.13407(9) 0.65401(7) 0.0275(3) Uani 1 d . . .
O4 O 0.20038(15) 0.85563(9) 0.34450(6) 0.0255(3) Uani 1 d . . .
O5 O 0.32950(15) 0.64427(9) 0.41821(6) 0.0261(3) Uani 1 d . . .
H5 H 0.2879 0.6903 0.3769 0.039 Uiso 1 d . . R
N1 N 0.38242(16) 0.91462(10) 0.75108(7) 0.0200(3) Uani 1 d . . .
C1 C 0.37730(19) 0.85445(13) 0.65857(8) 0.0177(3) Uani 1 d . . .
C2 C 0.31757(19) 0.92350(13) 0.58231(9) 0.0175(3) Uani 1 d . . .
C3 C 0.28187(19) 1.06983(13) 0.58604(9) 0.0191(3) Uani 1 d . . .
C4 C 0.20518(18) 1.13369(13) 0.50308(9) 0.0179(3) Uani 1 d . . .
C5 C 0.17941(19) 1.06169(14) 0.42122(9) 0.0186(3) Uani 1 d . . .
C6 C 0.22618(18) 0.91865(13) 0.41622(8) 0.0186(3) Uani 1 d . . .
C7 C 0.29921(18) 0.85308(13) 0.49853(9) 0.0178(3) Uani 1 d . . .
C8 C 0.34683(19) 0.71732(13) 0.49467(9) 0.0197(3) Uani 1 d . . .
C9 C 0.4135(2) 0.65386(13) 0.57285(9) 0.0208(3) Uani 1 d . . .
H9 H 0.4474 0.5652 0.5696 0.025 Uiso 1 calc . . R
C10 C 0.42912(19) 0.72168(13) 0.65460(9) 0.0199(3) Uani 1 d . . .
H10 H 0.4738 0.6795 0.7066 0.024 Uiso 1 calc . . R
C11 C 0.11238(19) 1.12535(14) 0.34352(9) 0.0206(3) Uani 1 d . . .
H11 H 0.0969 1.0782 0.2891 0.025 Uiso 1 calc . . R
C12 C 0.0686(2) 1.25920(14) 0.34729(9) 0.0225(3) Uani 1 d . . .
H12 H 0.0225 1.3013 0.2956 0.027 Uiso 1 calc . . R
C13 C 0.09378(19) 1.33044(14) 0.42847(9) 0.0225(3) Uani 1 d . . .
H13 H 0.0648 1.4201 0.4306 0.027 Uiso 1 calc . . R
C14 C 0.1618(2) 1.26829(14) 0.50608(9) 0.0213(3) Uani 1 d . . .
H14 H 0.1785 1.3163 0.5601 0.026 Uiso 1 calc . . R


_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 N1 1.2205(16) . ?
O2 N1 1.2220(16) . ?
O3 C3 1.2178(16) . ?
O4 C6 1.2356(16) . ?
O5 H5 0.8204 . ?
O5 C8 1.3387(15) . ?
N1 C1 1.4730(16) . ?
C1 C2 1.3835(18) . ?
C1 C10 1.3934(19) . ?
C2 C3 1.5001(19) . ?
C2 C7 1.4152(18) . ?
C3 C4 1.4829(18) . ?
C4 C5 1.4065(18) . ?
C4 C14 1.3951(19) . ?
C5 C6 1.4847(19) . ?
C5 C11 1.3928(18) . ?
C6 C7 1.4724(18) . ?
C7 C8 1.4143(19) . ?
C8 C9 1.3965(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.3747(18) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.3935(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.3875(18) . ?
C14 H14 0.9300 . ?

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 O5 H5 109.5 . . ?
O1 N1 O2 124.73(11) . . ?
O1 N1 C1 117.63(11) . . ?
O2 N1 C1 117.45(11) . . ?
C2 C1 N1 122.19(11) . . ?
C2 C1 C10 122.73(12) . . ?
C10 C1 N1 115.02(11) . . ?
C1 C2 C3 121.60(12) . . ?
C1 C2 C7 117.93(12) . . ?
C7 C2 C3 120.40(11) . . ?
O3 C3 C2 120.61(12) . . ?
O3 C3 C4 121.52(12) . . ?
C4 C3 C2 117.81(11) . . ?
C5 C4 C3 121.16(12) . . ?
C14 C4 C3 119.13(12) . . ?
C14 C4 C5 119.69(12) . . ?
C4 C5 C6 120.60(12) . . ?
C11 C5 C4 119.85(13) . . ?
C11 C5 C6 119.53(12) . . ?
O4 C6 C5 120.19(12) . . ?
O4 C6 C7 120.86(12) . . ?
C7 C6 C5 118.94(11) . . ?
C2 C7 C6 120.70(12) . . ?
C8 C7 C2 119.56(12) . . ?
C8 C7 C6 119.72(12) . . ?
O5 C8 C7 122.63(12) . . ?
O5 C8 C9 117.28(12) . . ?
C9 C8 C7 120.08(12) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.42(12) . . ?
C10 C9 H9 119.8 . . ?
C1 C10 H10 120.4 . . ?
C9 C10 C1 119.19(12) . . ?
C9 C10 H10 120.4 . . ?
C5 C11 H11 120.0 . . ?
C12 C11 C5 120.05(13) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.08(12) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.36(13) . . ?
C14 C13 H13 119.8 . . ?
C4 C14 H14 120.0 . . ?
C13 C14 C4 119.96(13) . . ?
C13 C14 H14 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 67.19(17) . . . . ?
O1 N1 C1 C10 -110.06(14) . . . . ?
O2 N1 C1 C2 -117.58(14) . . . . ?
O2 N1 C1 C10 65.17(16) . . . . ?
O3 C3 C4 C5 172.64(13) . . . . ?
O3 C3 C4 C14 -5.9(2) . . . . ?
O4 C6 C7 C2 -175.90(12) . . . . ?
O4 C6 C7 C8 2.3(2) . . . . ?
O5 C8 C9 C10 -177.85(12) . . . . ?
N1 C1 C2 C3 9.7(2) . . . . ?
N1 C1 C2 C7 -173.36(11) . . . . ?
N1 C1 C10 C9 174.35(12) . . . . ?
C1 C2 C3 O3 7.1(2) . . . . ?
C1 C2 C3 C4 -175.57(12) . . . . ?
C1 C2 C7 C6 176.41(11) . . . . ?
C1 C2 C7 C8 -1.8(2) . . . . ?
C2 C1 C10 C9 -2.9(2) . . . . ?
C2 C3 C4 C5 -4.7(2) . . . . ?
C2 C3 C4 C14 176.75(12) . . . . ?
C2 C7 C8 O5 178.68(12) . . . . ?
C2 C7 C8 C9 -0.7(2) . . . . ?
C3 C2 C7 C6 -6.6(2) . . . . ?
C3 C2 C7 C8 175.18(12) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C3 C4 C5 C11 -178.01(12) . . . . ?
C3 C4 C14 C13 178.55(12) . . . . ?
C4 C5 C6 O4 178.84(12) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C4 C5 C11 C12 -0.9(2) . . . . ?
C5 C4 C14 C13 -0.1(2) . . . . ?
C5 C6 C7 C2 2.6(2) . . . . ?
C5 C6 C7 C8 -179.15(12) . . . . ?
C5 C11 C12 C13 0.8(2) . . . . ?
C6 C5 C11 C12 -179.82(12) . . . . ?
C6 C7 C8 O5 0.4(2) . . . . ?
C6 C7 C8 C9 -178.98(12) . . . . ?
C7 C2 C3 O3 -169.80(13) . . . . ?
C7 C2 C3 C4 7.5(2) . . . . ?
C7 C8 C9 C10 1.6(2) . . . . ?
C8 C9 C10 C1 0.2(2) . . . . ?
C10 C1 C2 C3 -173.29(13) . . . . ?
C10 C1 C2 C7 3.7(2) . . . . ?
C11 C5 C6 O4 -2.3(2) . . . . ?
C11 C5 C6 C7 179.19(12) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C4 -0.1(2) . . . . ?
C14 C4 C5 C6 179.46(13) . . . . ?
C14 C4 C5 C11 0.6(2) . . . . ?

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 -4 7 0.0161 0.0049 -3.9979 6.9969 0.8841 0.3779 0.0368
0 4 -7 0.0561 -0.0049 3.9979 -6.9969 -0.8841 -0.3779 -0.0368
0 5 7 0.0662 -0.0062 5.0004 7.0014 -0.3286 1.0093 -0.1013
0 -5 -7 0.0422 0.0062 -5.0004 -7.0014 0.3286 -1.0093 0.1013
5 0 -1 0.2283 5.0022 0.0016 -0.9945 0.0230 -0.1880 -1.0394
-5 0 1 0.2283 -5.0022 -0.0016 0.9945 -0.0230 0.1880 1.0394

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_st298-Cu-300K_3_abs
_database_code_depnum_ccdc_archive 'CCDC 1419048'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        1-Hydroxy-4-Nitroanthraquinone
_chemical_formula_moiety         'C14 H7 N O5'
_chemical_formula_sum            'C14 H7 N O5'
_chemical_formula_weight         269.22
_chemical_oxdiff_formula         'C14 O5 N1 H7'
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
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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.4696(3)
_cell_length_b                   10.1464(4)
_cell_length_c                   14.5732(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.118(4)
_cell_angle_gamma                90
_cell_volume                     1104.49(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1971
_cell_measurement_theta_max      70.9600
_cell_measurement_theta_min      6.6480
_exptl_absorpt_coefficient_mu    1.071
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.754
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.6189
_exptl_crystal_description       block
_exptl_crystal_F_000             554.0933
_exptl_crystal_size_max          0.4342
_exptl_crystal_size_mid          0.1232
_exptl_crystal_size_min          0.0895
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5794
_diffrn_reflns_theta_full        71.0374
_diffrn_reflns_theta_max         71.04
_diffrn_reflns_theta_min         5.31
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.9421
_diffrn_measured_fraction_theta_max 0.9421
_cell_measurement_temperature    300
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   33.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega    7.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -120.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega -127.00  -62.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -54.7500  -37.0000  120.0000 65

#__ type_ start__ end____ width___ exp.time_
  5 omega  -15.00   34.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       54.7500  -37.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   83.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       54.7500  -99.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega   44.00   80.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -50.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
  8 omega   40.00   66.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -37.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   44.00   72.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00   64.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   81.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
 12 omega   53.00   79.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -120.0000   -9.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   79.00  135.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000   25.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
 14 omega  138.00  172.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000   25.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
 15 omega   53.00   79.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   37.00   71.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00  133.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -93.0000   65.8840 96

#__ type_ start__ end____ width___ exp.time_
 18 omega  -71.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
 19 omega  -71.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
 20 omega  -14.00   76.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       54.7500  -57.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 21 omega   23.00  126.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
 22 omega   23.00  126.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       54.7500   77.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 23 omega   27.00  127.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       54.7500   37.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
 24 omega  -71.00   -2.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -75.0000   37.0000 -180.0000 69

#__ type_ start__ end____ width___ exp.time_
 25 omega   35.00   72.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
 26 omega   37.00  149.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -91.0000 -150.0000 112

#__ type_ start__ end____ width___ exp.time_
 27 omega   70.00  178.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000   25.0000   60.0000 108

#__ type_ start__ end____ width___ exp.time_
 28 omega   35.00   72.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -25.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 29 omega   86.00  178.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000   50.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
 30 omega   86.00  103.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      109.5000   50.0000 -180.0000 17
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0273392000
_diffrn_orient_matrix_UB_12      0.1489661000
_diffrn_orient_matrix_UB_13      0.0146612000
_diffrn_orient_matrix_UB_21      0.0390394000
_diffrn_orient_matrix_UB_22      -0.0170694000
_diffrn_orient_matrix_UB_23      0.1031549000
_diffrn_orient_matrix_UB_31      0.2007124000
_diffrn_orient_matrix_UB_32      0.0236005000
_diffrn_orient_matrix_UB_33      -0.0179115000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -7
_reflns_number_gt                1358
_reflns_number_total             2018
_reflns_odcompleteness_completeness 88.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     I>=2u(I)
_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)'
_refine_diff_density_max         0.4555
_refine_diff_density_min         -0.5854
_refine_diff_density_rms         0.1386
_refine_ls_d_res_high            0.8152
_refine_ls_d_res_low             8.3269
_refine_ls_goodness_of_fit_ref   1.1051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.1051
_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)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1919
_refine_ls_wR_factor_ref         0.2836
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_primary     direct
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 0.2439(4) 0.4402(3) 0.21278(16) 0.0607(8) Uani 1.000000 .
O2 O 0.5297(4) 0.4283(3) 0.21535(19) 0.0719(9) Uani 1.000000 .
O3 O 0.3223(4) 0.6309(2) 0.34772(17) 0.0649(9) Uani 1.000000 .
O4 O 0.1984(4) 0.3532(2) 0.65449(16) 0.0566(7) Uani 1.000000 .
O5 O 0.3263(4) 0.1434(2) 0.57994(16) 0.0597(8) Uani 1.000000 .
H5 H 0.2812(4) 0.1887(2) 0.62040(16) 0.0896(12) Uiso 1.000000 R
N1 N 0.3869(4) 0.4149(2) 0.25031(16) 0.0428(7) Uani 1.000000 .
C1 C 0.3778(4) 0.3540(3) 0.34220(19) 0.0343(7) Uani 1.000000 .
C2 C 0.3179(4) 0.4219(3) 0.41781(18) 0.0312(7) Uani 1.000000 .
C3 C 0.2833(4) 0.5674(3) 0.41501(19) 0.0355(7) Uani 1.000000 .
C4 C 0.2059(4) 0.6295(3) 0.49786(19) 0.0348(7) Uani 1.000000 .
C5 C 0.1803(4) 0.5582(3) 0.5792(2) 0.0360(7) Uani 1.000000 .
C6 C 0.2261(4) 0.4160(3) 0.58332(19) 0.0370(7) Uani 1.000000 .
C7 C 0.2976(4) 0.3514(3) 0.50132(18) 0.0334(7) Uani 1.000000 .
C8 C 0.3458(4) 0.2162(3) 0.5035(2) 0.0395(7) Uani 1.000000 .
C9 C 0.4098(4) 0.1542(3) 0.4260(2) 0.0437(8) Uani 1.000000 .
H9 H 0.4417(4) 0.0656(3) 0.4287(2) 0.0524(10) Uiso 1.000000 R
C10 C 0.4268(4) 0.2217(3) 0.3451(2) 0.0407(8) Uani 1.000000 .
H10 H 0.4705(4) 0.1798(3) 0.2929(2) 0.0489(9) Uiso 1.000000 R
C11 C 0.1114(4) 0.6203(3) 0.6568(2) 0.0418(8) Uani 1.000000 .
H11 H 0.0926(4) 0.5727(3) 0.7105(2) 0.0501(9) Uiso 1.000000 R
C12 C 0.0711(4) 0.7537(3) 0.6535(2) 0.0464(8) Uani 1.000000 .
H12 H 0.0272(4) 0.7959(3) 0.7055(2) 0.0556(10) Uiso 1.000000 R
C13 C 0.0958(5) 0.8242(3) 0.5736(2) 0.0487(9) Uani 1.000000 .
H13 H 0.0660(5) 0.9132(3) 0.5718(2) 0.0584(10) Uiso 1.000000 R
C14 C 0.1648(4) 0.7639(3) 0.4959(2) 0.0428(8) Uani 1.000000 .
H14 H 0.1836(4) 0.8126(3) 0.4427(2) 0.0514(9) Uiso 1.000000 R


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 N1 1.226(4) . ?
O2 N1 1.191(4) . ?
O3 C3 1.210(3) . ?
O4 C6 1.235(3) . ?
O5 H5 0.8205 . ?
O5 C8 1.344(3) . ?
N1 C1 1.476(3) . ?
C1 C2 1.375(4) . ?
C1 C10 1.393(4) . ?
C2 C3 1.499(4) . ?
C2 C7 1.420(4) . ?
C3 C4 1.481(4) . ?
C4 C5 1.402(4) . ?
C4 C14 1.397(4) . ?
C5 C6 1.484(4) . ?
C5 C11 1.395(4) . ?
C6 C7 1.465(4) . ?
C7 C8 1.419(4) . ?
C8 C9 1.379(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.388(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(4) . ?
C14 H14 0.9300 . ?

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 O5 H5 109.5 . . ?
O2 N1 O1 124.4(3) . . ?
C1 N1 O1 116.8(3) . . ?
C1 N1 O2 118.6(3) . . ?
C2 C1 N1 122.2(2) . . ?
C10 C1 N1 114.7(2) . . ?
C10 C1 C2 123.0(3) . . ?
C3 C2 C1 121.9(2) . . ?
C7 C2 C1 118.0(2) . . ?
C7 C2 C3 120.0(2) . . ?
C2 C3 O3 120.3(2) . . ?
C4 C3 O3 122.0(3) . . ?
C4 C3 C2 117.7(2) . . ?
C5 C4 C3 121.6(3) . . ?
C14 C4 C3 119.0(3) . . ?
C14 C4 C5 119.4(3) . . ?
C6 C5 C4 120.3(2) . . ?
C11 C5 C4 120.2(3) . . ?
C11 C5 C6 119.5(3) . . ?
C5 C6 O4 119.8(3) . . ?
C7 C6 O4 121.1(3) . . ?
C7 C6 C5 119.1(2) . . ?
C6 C7 C2 120.9(2) . . ?
C8 C7 C2 118.6(3) . . ?
C8 C7 C6 120.5(3) . . ?
C7 C8 O5 121.5(3) . . ?
C9 C8 O5 117.8(3) . . ?
C9 C8 C7 120.7(3) . . ?
H9 C9 C8 119.68(17) . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.68(17) . . ?
C9 C10 C1 118.9(3) . . ?
H10 C10 C1 120.55(17) . . ?
H10 C10 C9 120.55(17) . . ?
H11 C11 C5 120.22(18) . . ?
C12 C11 C5 119.6(3) . . ?
C12 C11 H11 120.22(18) . . ?
H12 C12 C11 119.82(18) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.82(18) . . ?
H13 C13 C12 119.65(18) . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.65(19) . . ?
C13 C14 C4 119.7(3) . . ?
H14 C14 C4 120.14(17) . . ?
H14 C14 C13 120.14(19) . . ?

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 3 -8 0.0447 -0.0004 3.0038 -7.9952 0.3303 -0.8760 0.2140
0 -6 -2 0.0476 0.0010 -5.9996 -2.0019 -0.9231 -0.1041 -0.1055
0 6 2 0.0476 -0.0010 5.9996 2.0019 0.9231 0.1041 0.1055
-5 0 0 0.2170 -5.0008 -0.0048 0.0004 0.1360 -0.1951 -1.0038
0 -3 8 0.0447 0.0004 -3.0038 7.9952 -0.3303 0.8760 -0.2140
5 0 0 0.2170 5.0008 0.0048 -0.0004 -0.1360 0.1951 1.0038

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_st95-mo-120k_2_abs2
_database_code_depnum_ccdc_archive 'CCDC 1419049'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        'Lithium formate anhydrous'
_chemical_formula_moiety         'C4 H4 Li4 O8'
_chemical_formula_sum            'C4 H4 Li4 O8'
_chemical_formula_weight         207.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C4 O8 Li4 H4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.0297(5)
_cell_length_b                   12.0413(6)
_cell_length_c                   13.5174(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.597(4)
_cell_angle_gamma                90.00
_cell_volume                     1924.64(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10263
_cell_measurement_temperature    121(1)
_cell_measurement_theta_max      28.8400
_cell_measurement_theta_min      3.5880
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.959
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4923
_exptl_crystal_size_mid          0.2056
_exptl_crystal_size_min          0.1085
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33409
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         3.03
_diffrn_ambient_temperature      121(1)
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00   60.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379  -99.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00   42.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379  -99.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -84.00  -39.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -      -18.9754  178.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega  -80.00   53.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -      -18.9754    0.0000 -120.0000 133

#__ type_ start__ end____ width___ exp.time_
  5 omega  -52.00   48.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379  -77.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
  6 omega  -27.00   19.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379  106.0000   41.0000 46

#__ type_ start__ end____ width___ exp.time_
  7 omega  -39.00   50.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -      -18.9754   57.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
  8 omega  -95.00  -35.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -      -18.9754 -178.0000 -120.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega  -88.00    2.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -      -18.9754  -57.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
 10 omega  -91.00    7.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -      -18.9754  -37.0000   90.0000 98

#__ type_ start__ end____ width___ exp.time_
 11 omega   -4.00   60.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379  -99.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
 12 omega   -4.00   60.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379  -99.0000  -60.0000 64

#__ type_ start__ end____ width___ exp.time_
 13 omega   -3.00   87.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379   57.0000  120.0000 90

#__ type_ start__ end____ width___ exp.time_
 14 omega  -19.00   37.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379   90.0000  -47.0000 56

#__ type_ start__ end____ width___ exp.time_
 15 omega  -39.00   50.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -      -18.9754   57.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
 16 omega  -89.00   11.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -      -18.9754  -77.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 17 omega    3.00   63.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379 -106.0000  121.0000 60

#__ type_ start__ end____ width___ exp.time_
 18 omega  -12.00   88.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379   77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 19 omega  -12.00   88.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379   77.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
 20 omega   -4.00   60.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379  -99.0000   90.0000 64

#__ type_ start__ end____ width___ exp.time_
 21 omega  -64.00   19.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -      -18.9754  106.0000 -138.0000 83

#__ type_ start__ end____ width___ exp.time_
 22 omega  -56.00   37.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -      -18.9754   90.0000  132.0000 93

#__ type_ start__ end____ width___ exp.time_
 23 omega  -55.00    6.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -       18.0379    0.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
 24 omega  -39.00   50.00   1.0000   10.5100
omega____ theta____ kappa____ phi______ frames
    -      -18.9754   57.0000 -150.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0121136000
_diffrn_orient_matrix_UB_12      -0.0562296000
_diffrn_orient_matrix_UB_13      0.0134426000
_diffrn_orient_matrix_UB_21      0.0168706000
_diffrn_orient_matrix_UB_22      -0.0089612000
_diffrn_orient_matrix_UB_23      -0.0469230000
_diffrn_orient_matrix_UB_31      0.0562796000
_diffrn_orient_matrix_UB_32      0.0151003000
_diffrn_orient_matrix_UB_33      0.0215863000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1991
_reflns_number_total             2285
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_reflns_threshold_expression     >2sigma(I)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0614P)²+1.3013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1088
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.07147(7) 0.46458(8) 0.15013(7) 0.0261(2) Uani 1 d . . .
O2 O 0.01635(8) 0.32944(8) 0.03978(6) 0.0259(2) Uani 1 d . . .
O3 O 0.31983(7) 0.55186(8) 0.21437(6) 0.0267(2) Uani 1 d . . .
O4 O 0.43947(7) 0.59888(8) 0.11382(7) 0.0261(2) Uani 1 d . . .
O5 O 0.35097(7) 0.60218(8) 0.44075(7) 0.0269(2) Uani 1 d . . .
O6 O 0.16544(7) 0.57797(8) 0.39023(6) 0.0265(2) Uani 1 d . . .
O7 O 0.09489(8) 0.68948(8) 0.17960(7) 0.0266(2) Uani 1 d . . .
O8 O 0.06673(8) 0.86526(8) 0.13049(7) 0.0275(2) Uani 1 d . . .
C1 C 0.05468(10) 0.36533(11) 0.12651(9) 0.0249(3) Uani 1 d . . .
H1 H 0.0725 0.3119 0.1788 0.030 Uiso 1 calc . . R
C2 C 0.34372(11) 0.59207(11) 0.13522(9) 0.0252(3) Uani 1 d . . .
H2 H 0.2826 0.6200 0.0870 0.030 Uiso 1 calc . . R
C3 C 0.25138(11) 0.60509(11) 0.45343(9) 0.0258(3) Uani 1 d . . .
H3 H 0.2389 0.6303 0.5171 0.031 Uiso 1 calc . . R
C4 C 0.10865(11) 0.79107(12) 0.19147(9) 0.0265(3) Uani 1 d . . .
H4 H 0.1552 0.8150 0.2523 0.032 Uiso 1 calc . . R
Li1 Li 0.00306(19) 0.17137(18) 0.00759(16) 0.0262(4) Uani 1 d . . .
Li2 Li 0.16886(18) 0.55972(19) 0.24685(16) 0.0262(4) Uani 1 d . . .
Li3 Li 0.41907(18) 0.52205(19) 0.34048(16) 0.0259(4) Uani 1 d . . .
Li4 Li -0.01005(18) 0.59575(19) 0.08809(16) 0.0262(5) Uani 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 C1 1.2439(16) . ?
O2 C1 1.2550(15) . ?
O3 C2 1.2549(16) . ?
O4 C2 1.2409(16) . ?
O5 C3 1.2417(16) . ?
O6 C3 1.2571(15) . ?
O7 C4 1.2410(17) . ?
O8 C4 1.2565(16) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?

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
O1 C1 O2 125.81(12) . . ?
O1 C1 H1 117.1 . . ?
O2 C1 H1 117.1 . . ?
O3 C2 H2 116.8 . . ?
O4 C2 O3 126.31(11) . . ?
O4 C2 H2 116.8 . . ?
O5 C3 O6 126.35(12) . . ?
O5 C3 H3 116.8 . . ?
O6 C3 H3 116.8 . . ?
O7 C4 O8 126.02(12) . . ?
O7 C4 H4 117.0 . . ?
O8 C4 H4 117.0 . . ?

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
7 2 -18 0.1133 7.0025 2.0013 -18.0047 -0.2697 0.9450 0.0357
-7 -2 18 0.0923 -7.0025 -2.0013 18.0047 0.2697 -0.9450 -0.0357
16 5 1 0.1932 16.0003 5.0008 0.9971 -0.0740 0.1783 0.9975
-16 -5 -1 0.1932 -16.0003 -5.0008 -0.9971 0.0740 -0.1783 -0.9975
0 17 3 0.0847 0.0041 16.9969 3.0002 -0.9154 -0.2930 0.3216
0 -17 -3 0.0237 -0.0041 -16.9969 -3.0002 0.9154 0.2930 -0.3216
-6 16 1 0.1230 -5.9956 15.9965 1.0009 -0.9587 -0.2915 -0.0743

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_st95-mo-300k_2_abs
_database_code_depnum_ccdc_archive 'CCDC 1419050'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        'Lithium formate anhydrous'
_chemical_formula_moiety         'C4 H4 Li4 O8'
_chemical_formula_sum            'C4 H4 Li4 O8'
_chemical_formula_weight         207.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C4 O8 H4 Li4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.0519(3)
_cell_length_b                   12.0497(3)
_cell_length_c                   13.5108(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.003(3)
_cell_angle_gamma                90.00
_cell_volume                     1925.99(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3901
_cell_measurement_temperature    300.00(14)
_cell_measurement_theta_max      28.9200
_cell_measurement_theta_min      4.1670
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.958
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.2502
_exptl_crystal_size_min          0.1015
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12605
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         3.03
_diffrn_ambient_temperature      300.00(14)
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   18.00   1.0000   14.0900
omega____ theta____ kappa____ phi______ frames
    -       18.0379   90.0000  -47.0000 32

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   34.00   1.0000   14.0900
omega____ theta____ kappa____ phi______ frames
    -       18.0379  -99.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega  -81.00   22.00   1.0000   14.0900
omega____ theta____ kappa____ phi______ frames
    -      -18.9754  -19.0000 -120.0000 103

#__ type_ start__ end____ width___ exp.time_
  4 omega  -36.00   36.00   1.0000   14.0900
omega____ theta____ kappa____ phi______ frames
    -      -18.9754   57.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega   -4.00   60.00   1.0000   14.0900
omega____ theta____ kappa____ phi______ frames
    -       18.0379  -99.0000  -30.0000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega  -51.00  -26.00   1.0000   14.0900
omega____ theta____ kappa____ phi______ frames
    -       18.0379  -57.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -88.00    2.00   1.0000   14.0900
omega____ theta____ kappa____ phi______ frames
    -      -18.9754  -57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
  8 omega  -39.00   50.00   1.0000   14.0900
omega____ theta____ kappa____ phi______ frames
    -      -18.9754   57.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
  9 omega  -89.00   11.00   1.0000   14.0900
omega____ theta____ kappa____ phi______ frames
    -      -18.9754  -77.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
 10 omega  -95.00  -35.00   1.0000   14.0900
omega____ theta____ kappa____ phi______ frames
    -      -18.9754 -178.0000 -180.0000 60
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0100948000
_diffrn_orient_matrix_UB_12      -0.0564085000
_diffrn_orient_matrix_UB_13      -0.0137859000
_diffrn_orient_matrix_UB_21      -0.0181642000
_diffrn_orient_matrix_UB_22      -0.0101281000
_diffrn_orient_matrix_UB_23      0.0461423000
_diffrn_orient_matrix_UB_31      -0.0562336000
_diffrn_orient_matrix_UB_32      0.0133892000
_diffrn_orient_matrix_UB_33      -0.0232846000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1871
_reflns_number_total             2266
_reflns_odcompleteness_completeness 98.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_reflns_threshold_expression     >2sigma(I)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.6317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0843
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.33343(6) 0.42165(7) 0.61072(6) 0.0396(2) Uani 1 d . . .
O2 O 0.14891(7) 0.39820(7) 0.56014(6) 0.0410(2) Uani 1 d . . .
O3 O 0.59433(7) 0.30961(6) 0.67850(6) 0.0403(2) Uani 1 d . . .
O4 O 0.56701(7) 0.13495(7) 0.63021(6) 0.0417(2) Uani 1 d . . .
O5 O 0.56016(7) 0.09956(7) 0.38588(6) 0.0386(2) Uani 1 d . . .
O6 O 0.67930(7) 0.05380(7) 0.28653(6) 0.0403(2) Uani 1 d . . .
O7 O 0.57180(7) 0.53436(7) 0.64944(6) 0.0393(2) Uani 1 d . . .
O8 O 0.51846(7) 0.66977(6) 0.54035(6) 0.0396(2) Uani 1 d . . .
C1 C 0.24765(10) 0.39564(11) 0.54785(9) 0.0383(3) Uani 1 d . . .
H1 H 0.2593 0.3718 0.4852 0.046 Uiso 1 calc . . R
C2 C 0.60833(10) 0.20876(10) 0.69020(9) 0.0397(3) Uani 1 d . . .
H2 H 0.6544 0.1857 0.7499 0.048 Uiso 1 calc . . R
C3 C 0.65504(10) 0.09418(10) 0.36441(9) 0.0379(3) Uani 1 d . . .
H3 H 0.7145 0.1233 0.4113 0.045 Uiso 1 calc . . R
C4 C 0.55590(10) 0.63313(10) 0.62597(8) 0.0369(3) Uani 1 d . . .
H4 H 0.5738 0.6849 0.6776 0.044 Uiso 1 calc . . R
Li1 Li 0.33021(16) 0.43867(16) 0.75426(14) 0.0355(4) Uani 1 d . . .
Li2 Li 0.48819(16) 0.40404(16) 0.58801(14) 0.0363(4) Uani 1 d . . .
Li3 Li 0.49655(16) 0.17155(15) 0.49153(14) 0.0355(4) Uani 1 d . . .
Li4 Li 0.58084(16) 0.02173(16) 0.16011(14) 0.0363(4) Uani 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 C1 1.2464(14) . ?
O2 C1 1.2328(14) . ?
O3 C2 1.2329(14) . ?
O4 C2 1.2416(14) . ?
O5 C3 1.2338(14) . ?
O6 C3 1.2437(14) . ?
O7 C4 1.2372(14) . ?
O8 C4 1.2399(14) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?

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
O1 C1 H1 116.6 . . ?
O2 C1 O1 126.75(11) . . ?
O2 C1 H1 116.6 . . ?
O3 C2 O4 126.46(11) . . ?
O3 C2 H2 116.8 . . ?
O4 C2 H2 116.8 . . ?
O5 C3 O6 126.70(11) . . ?
O5 C3 H3 116.7 . . ?
O6 C3 H3 116.7 . . ?
O7 C4 O8 126.34(11) . . ?
O7 C4 H4 116.8 . . ?
O8 C4 H4 116.8 . . ?

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
1 17 -4 0.0633 1.0086 17.0090 -3.9984 -0.9145 -0.3751 0.2641
-1 -17 4 0.0383 -1.0086 -17.0090 3.9984 0.9145 0.3751 -0.2641
-12 3 -11 0.2389 -12.0106 3.0049 -10.9960 0.1033 -0.3197 0.9717
12 -3 11 0.2389 12.0106 -3.0049 10.9960 -0.1033 0.3197 -0.9717
15 -5 -10 0.0971 14.9952 -4.9909 -9.9848 0.2678 -0.6825 -0.6776
-15 5 10 0.2331 -14.9952 4.9909 9.9848 -0.2678 0.6825 0.6776
-5 3 19 0.1251 -4.9862 2.9871 18.9815 -0.3798 0.9362 -0.1216
5 -3 -19 0.1251 4.9862 -2.9871 -18.9815 0.3798 -0.9362 0.1216
-12 -12 0 0.2015 -12.0124 -12.0077 -0.0034 0.7986 0.3397 0.5148
12 12 0 0.2015 12.0124 12.0077 0.0034 -0.7986 -0.3397 -0.5148

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
