#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/22/7222256.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7222256
loop_
_publ_author_name
'Silberstein, Katharine E.'
'Pastore, James P.'
'Zhou, Weidong'
'Potash, Rebecca A.'
'Hernández-Burgos, Kenneth'
'Lobkovsky, Emil B.'
'Abruña, Héctor D'
_publ_section_title
;
 Electrochemical lithiation-induced polymorphism of anthraquinone
 derivatives observed by operando X-ray diffraction.
;
_journal_issue                   41
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              27665
_journal_page_last               27671
_journal_paper_doi               10.1039/c5cp04201a
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C16 H8 O6, 2(C3 H7 N O)'
_chemical_formula_sum            'C22 H22 N2 O8'
_chemical_formula_weight         442.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-17 deposited with the CCDC.
2015-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.490(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.8170(11)
_cell_length_b                   7.3554(6)
_cell_length_c                   11.1126(8)
_cell_measurement_reflns_used    3344
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.97
_cell_measurement_theta_min      3.20
_cell_volume                     1036.15(14)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9942
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         3.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.2763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2023
_reflns_number_total             2563
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cp04201a1.cif
_cod_data_source_block           wz5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7222256.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7222256
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.20305(7) 0.00564(13) 0.46548(9) 0.0325(2) Uani 1 1 d
O2 O 0.25576(7) 0.39650(14) 0.46651(9) 0.0312(2) Uani 1 1 d
O3 O 0.21211(8) 0.33843(15) 0.26745(9) 0.0335(2) Uani 1 1 d
H3O H 0.2846(18) 0.367(3) 0.2640(19) 0.074(7) Uiso 1 1 d
C1 C 0.11175(9) 0.00704(16) 0.48474(11) 0.0208(2) Uani 1 1 d
C2 C 0.04015(9) 0.16122(16) 0.44355(10) 0.0195(2) Uani 1 1 d
C3 C -0.06761(9) 0.15007(16) 0.45425(10) 0.0197(2) Uani 1 1 d
C4 C -0.13634(10) 0.28901(18) 0.40926(11) 0.0239(3) Uani 1 1 d
H4 H -0.2105(12) 0.279(2) 0.4191(14) 0.028(4) Uiso 1 1 d
C5 C -0.09921(10) 0.43839(18) 0.35249(12) 0.0262(3) Uani 1 1 d
H5 H -0.1446(12) 0.535(2) 0.3204(14) 0.032(4) Uiso 1 1 d
C6 C 0.00733(10) 0.45067(18) 0.34228(11) 0.0244(3) Uani 1 1 d
H6 H 0.0346(12) 0.556(2) 0.3052(14) 0.030(4) Uiso 1 1 d
C7 C 0.07778(9) 0.31476(17) 0.38840(11) 0.0207(3) Uani 1 1 d
C8 C 0.19289(9) 0.34919(16) 0.37998(11) 0.0224(3) Uani 1 1 d
O1S O 0.59701(8) 0.91143(16) 0.25584(10) 0.0388(3) Uani 1 1 d
N1S N 0.47443(8) 0.83079(16) 0.37355(10) 0.0276(3) Uani 1 1 d
C1S C 0.57200(11) 0.84106(19) 0.34943(13) 0.0297(3) Uani 1 1 d
H1S H 0.6247(12) 0.784(2) 0.4133(14) 0.030(4) Uiso 1 1 d
C2S C 0.44988(14) 0.7412(2) 0.48315(15) 0.0372(4) Uani 1 1 d
H2SC H 0.4085(14) 0.633(3) 0.4642(16) 0.049(5) Uiso 1 1 d
H2SB H 0.4107(16) 0.829(3) 0.5281(18) 0.062(6) Uiso 1 1 d
H2SA H 0.5159(16) 0.705(3) 0.5343(18) 0.053(5) Uiso 1 1 d
C3S C 0.38567(13) 0.8965(3) 0.28829(16) 0.0463(4) Uani 1 1 d
H3SC H 0.4088(15) 0.945(3) 0.2129(19) 0.056(5) Uiso 1 1 d
H3SB H 0.3449(19) 0.986(3) 0.323(2) 0.078(7) Uiso 1 1 d
H3SA H 0.338(2) 0.789(4) 0.263(3) 0.101(9) Uiso 1 1 d
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
O1 C1 C2 121.09(11) .
O1 C1 C3 120.70(11) 3_556
C2 C1 C3 118.16(10) 3_556
C7 C2 C3 119.27(10) .
C7 C2 C1 120.76(10) .
C3 C2 C1 119.90(10) .
C4 C3 C2 120.26(11) .
C4 C3 C1 117.97(10) 3_556
C2 C3 C1 121.76(10) 3_556
C5 C4 C3 120.24(11) .
C4 C5 C6 119.75(12) .
C5 C6 C7 120.97(12) .
C6 C7 C2 119.48(11) .
C6 C7 C8 116.24(11) .
C2 C7 C8 124.22(11) .
O2 C8 O3 125.28(11) .
O2 C8 C7 122.65(11) .
O3 C8 C7 111.76(10) .
C1S N1S C3S 121.56(12) .
C1S N1S C2S 121.54(12) .
C3S N1S C2S 116.76(13) .
O1S C1S N1S 124.20(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2204(14) .
O2 C8 1.2108(15) .
O3 C8 1.3122(15) .
C1 C2 1.4878(16) .
C1 C3 1.4928(16) 3_556
C2 C7 1.4040(17) .
C2 C3 1.4060(15) .
C3 C4 1.3929(17) .
C3 C1 1.4928(16) 3_556
C4 C5 1.3858(19) .
C5 C6 1.3898(18) .
C6 C7 1.3930(17) .
C7 C8 1.5134(16) .
O1S C1S 1.2453(17) .
N1S C1S 1.3192(17) .
N1S C3S 1.4516(19) .
N1S C2S 1.4593(18) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O1S 0.96(2) 1.60(2) 2.5550(13) 174(2) 2_645
