# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1854769'
_audit_update_record             
;
2018-07-10 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
N,N?-Dimethyl-2,6-Diaza-9,10-Anthrahydroquinonediium
_chemical_name_common            DAAQH2
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 N2 O2 2+, 2 Cl 1-'
_chemical_formula_sum            'C14 H14 Cl2 N2 O2'
_chemical_formula_weight         313.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.4516(10)
_cell_length_b                   6.7274(16)
_cell_length_c                   11.4945(18)
_cell_angle_alpha                86.957(9)
_cell_angle_beta                 83.772(8)
_cell_angle_gamma                77.680(11)
_cell_volume                     334.16(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1488
_cell_measurement_theta_min      7.66
_cell_measurement_theta_max      73.7

_exptl_crystal_description       lath
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             162
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    4.400
_shelx_estimated_absorpt_T_min   0.418
_shelx_estimated_absorpt_T_max   0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.27t (Agilent, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed microfocus tube'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1304
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         3.870
_diffrn_reflns_theta_max         74.173
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1304
_reflns_number_gt                1282
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;



_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'





_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0987P)²+0.0596P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1304
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8245(3) 0.75876(18) 0.58886(11) 0.0158(3) Uani 1 1 d . . . . .
H1O H 0.8863 0.7376 0.6622 0.024 Uiso 1 1 d R U . . .
N1 N 0.5424(3) 0.2779(2) 0.79702(14) 0.0134(4) Uani 1 1 d . . . . .
C1 C 0.6655(4) 0.6311(3) 0.55030(15) 0.0130(4) Uani 1 1 d . . . . .
C2 C 0.5678(4) 0.4686(3) 0.61617(15) 0.0129(4) Uani 1 1 d . . . . .
C3 C 0.6259(4) 0.4314(3) 0.73519(15) 0.0136(4) Uani 1 1 d . . . . .
H3 H 0.7272 0.5191 0.7711 0.016 Uiso 1 1 calc R U . . .
C4 C 0.3896(4) 0.1469(3) 0.75063(16) 0.0155(4) Uani 1 1 d . . . . .
H4 H 0.3342 0.0370 0.7974 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3186(4) 0.1750(3) 0.63833(16) 0.0143(4) Uani 1 1 d . . . . .
H5 H 0.2099 0.0861 0.6073 0.017 Uiso 1 1 calc R U . . .
C6 C 0.4058(4) 0.3376(3) 0.56604(16) 0.0134(4) Uani 1 1 d . . . . .
C13 C 0.6083(5) 0.2451(3) 0.92116(16) 0.0188(4) Uani 1 1 d . . . . .
H13A H 0.7242 0.3450 0.9412 0.028 Uiso 1 1 calc R U . . .
H13B H 0.7310 0.1074 0.9326 0.028 Uiso 1 1 calc R U . . .
H13C H 0.4133 0.2613 0.9718 0.028 Uiso 1 1 calc R U . . .
Cl1 Cl 1.02914(8) 0.74617(5) 0.83154(3) 0.0160(2) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0168(6) 0.0135(7) 0.0202(7) -0.0013(5) -0.0054(5) -0.0080(5)
N1 0.0101(7) 0.0122(7) 0.0178(8) -0.0023(6) -0.0010(5) -0.0017(6)
C1 0.0073(7) 0.0113(8) 0.0206(9) -0.0038(6) -0.0015(6) -0.0011(6)
C2 0.0080(7) 0.0102(8) 0.0198(8) -0.0030(7) -0.0001(6) -0.0003(6)
C3 0.0087(8) 0.0120(8) 0.0202(9) -0.0046(7) -0.0009(6) -0.0014(6)
C4 0.0110(8) 0.0127(9) 0.0230(9) -0.0009(7) -0.0013(7) -0.0031(7)
C5 0.0093(8) 0.0106(8) 0.0235(9) -0.0020(7) -0.0011(7) -0.0033(7)
C6 0.0076(8) 0.0109(8) 0.0205(9) -0.0026(7) 0.0008(6) 0.0004(6)
C13 0.0214(10) 0.0172(9) 0.0179(8) -0.0018(7) -0.0027(7) -0.0034(8)
Cl1 0.0146(3) 0.0145(3) 0.0206(3) -0.00351(19) -0.0033(2) -0.0057(2)

_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 1.343(2) . ?
O1 H1O 0.9096 . ?
N1 C3 1.319(2) . ?
N1 C4 1.382(2) . ?
N1 C13 1.483(2) . ?
C1 C6 1.402(3) 2_666 ?
C1 C2 1.415(3) . ?
C2 C3 1.419(2) . ?
C2 C6 1.430(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.356(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.433(3) . ?
C5 H5 0.9500 . ?
C6 C1 1.402(3) 2_666 ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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 H1O 118.8 . . ?
C3 N1 C4 122.14(16) . . ?
C3 N1 C13 119.52(15) . . ?
C4 N1 C13 118.32(16) . . ?
O1 C1 C6 116.40(16) . 2_666 ?
O1 C1 C2 125.75(16) . . ?
C6 C1 C2 117.84(17) 2_666 . ?
C1 C2 C3 120.77(17) . . ?
C1 C2 C6 121.49(17) . . ?
C3 C2 C6 117.73(16) . . ?
N1 C3 C2 121.50(16) . . ?
N1 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C5 C4 N1 120.01(16) . . ?
C5 C4 H4 120.0 . . ?
N1 C4 H4 120.0 . . ?
C4 C5 C6 120.63(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C2 120.66(17) 2_666 . ?
C1 C6 C5 121.38(17) 2_666 . ?
C2 C6 C5 117.96(17) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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 2.2(3) . . . . ?
C6 C1 C2 C3 -178.51(14) 2_666 . . . ?
O1 C1 C2 C6 -178.36(16) . . . . ?
C6 C1 C2 C6 1.0(3) 2_666 . . . ?
C4 N1 C3 C2 -1.1(3) . . . . ?
C13 N1 C3 C2 179.97(15) . . . . ?
C1 C2 C3 N1 -178.49(15) . . . . ?
C6 C2 C3 N1 2.0(2) . . . . ?
C3 N1 C4 C5 -0.5(3) . . . . ?
C13 N1 C4 C5 178.37(16) . . . . ?
N1 C4 C5 C6 1.2(3) . . . . ?
C1 C2 C6 C1 -1.0(3) . . . 2_666 ?
C3 C2 C6 C1 178.50(14) . . . 2_666 ?
C1 C2 C6 C5 179.23(15) . . . . ?
C3 C2 C6 C5 -1.3(2) . . . . ?
C4 C5 C6 C1 179.94(16) . . . 2_666 ?
C4 C5 C6 C2 -0.3(3) . . . . ?

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
O1 H1O Cl1 0.91 2.12 3.0185(14) 169.5 .
C3 H3 Cl1 0.95 2.41 3.3519(18) 170.7 .
C4 H4 Cl1 0.95 2.60 3.4586(19) 150.4 1_445
C13 H13A Cl1 0.98 2.93 3.427(2) 112.6 2_767
C13 H13B Cl1 0.98 2.76 3.620(2) 147.1 1_545
C13 H13C Cl1 0.98 2.84 3.786(2) 162.8 2_667

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.112

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7

TITL shelx     P -1         R =  New: P-1  red laths
CELL  1.54184   4.4516   6.7274  11.4945   86.957   83.772   77.68
ZERR     1.00   0.0010   0.0016   0.0018    0.009    0.008    0.011
LATT   1
SFAC  C    H    CL   N    O
UNIT  14   14   2    2    2
MERG   2
rem rigu
HTAB O1 Cl1
HTAB C3 Cl1
EQIV $1 x-1, y-1, z
HTAB C4 Cl1_$1
EQIV $2 -x+2, -y+1, -z+2
HTAB C13 Cl1_$2
EQIV $3 x, y-1, z
HTAB C13 Cl1_$3
EQIV $4 -x+1, -y+1, -z+2
HTAB C13 Cl1_$4
FMAP   2
ACTA
size .032 .13 .24
HTAB    2.00000
BOND   $H
CONF
LIST   4
L.S.  10
TEMP  -173.00
WGHT    0.098700    0.059600
FVAR       0.34097
O1    5    0.824550    0.758761    0.588855    11.00000    0.01681    0.01350 =
         0.02017   -0.00132   -0.00537   -0.00799
AFIX   3
H1O   2    0.886298    0.737611    0.662195    11.00000   -1.50000
AFIX   0
N1    4    0.542423    0.277873    0.797017    11.00000    0.01008    0.01224 =
         0.01780   -0.00227   -0.00098   -0.00168
C1    1    0.665461    0.631146    0.550297    11.00000    0.00733    0.01129 =
         0.02056   -0.00383   -0.00153   -0.00115
C2    1    0.567808    0.468591    0.616174    11.00000    0.00798    0.01018 =
         0.01981   -0.00301   -0.00013   -0.00032
C3    1    0.625896    0.431407    0.735194    11.00000    0.00874    0.01197 =
         0.02017   -0.00461   -0.00089   -0.00143
AFIX  43
H3    2    0.727230    0.519134    0.771143    11.00000   -1.20000
AFIX   0
C4    1    0.389588    0.146857    0.750628    11.00000    0.01098    0.01271 =
         0.02298   -0.00088   -0.00133   -0.00308
AFIX  43
H4    2    0.334243    0.037020    0.797399    11.00000   -1.20000
AFIX   0
C5    1    0.318562    0.175027    0.638331    11.00000    0.00933    0.01057 =
         0.02351   -0.00202   -0.00107   -0.00327
AFIX  43
H5    2    0.209906    0.086111    0.607306    11.00000   -1.20000
AFIX   0
C6    1    0.405842    0.337620    0.566037    11.00000    0.00761    0.01093 =
         0.02047   -0.00257    0.00079    0.00042
C13   1    0.608321    0.245138    0.921159    11.00000    0.02143    0.01720 =
         0.01790   -0.00175   -0.00270   -0.00335
AFIX 137
H13A  2    0.724185    0.345018    0.941161    11.00000   -1.50000
H13B  2    0.730969    0.107423    0.932565    11.00000   -1.50000
H13C  2    0.413342    0.261350    0.971763    11.00000   -1.50000
AFIX   0
CL1   3    1.029139    0.746166    0.831538    11.00000    0.01460    0.01453 =
         0.02063   -0.00351   -0.00333   -0.00573
HKLF    4

REM  shelx     P -1         R =  New: P-1  red laths
REM R1 =  0.0429 for    1282 Fo > 4sig(Fo)  and  0.0431 for all    1304 data
REM     92 parameters refined using      0 restraints

END

WGHT      0.0964      0.0875

REM Instructions for potential hydrogen bonds
HTAB O1 Cl1
HTAB C3 Cl1
HTAB C4 Cl1_$1
HTAB C13 Cl1_$2
HTAB C13 Cl1_$3
HTAB C13 Cl1_$4

REM Highest difference peak  0.459,  deepest hole -0.573,  1-sigma level  0.112
Q1    1   0.9932  0.8492  0.8975  11.00000  0.05    0.46
Q2    1   1.0437  0.6401  0.7741  11.00000  0.05    0.41
Q3    1   1.2426  0.6435  0.8001  11.00000  0.05    0.39
Q4    1   0.8045  0.7253  0.8254  11.00000  0.05    0.38
Q5    1   0.7915  0.8356  0.8737  11.00000  0.05    0.36
Q6    1   0.4824  0.5806  0.8163  11.00000  0.05    0.35
Q7    1   1.2905  0.5090  0.8789  11.00000  0.05    0.34
Q8    1   0.5609  0.7811  0.7866  11.00000  0.05    0.32
Q9    1   0.6879  1.0062  0.6405  11.00000  0.05    0.32
Q10   1   1.2623  0.7615  0.8369  11.00000  0.05    0.32
Q11   1   0.2575  0.5249  0.6987  11.00000  0.05    0.32
Q12   1   0.0600  0.4827  0.5543  11.00000  0.05    0.30
Q13   1   0.7618 -0.0189  0.8977  11.00000  0.05    0.29
Q14   1   0.8365  0.0052  0.8804  11.00000  0.05    0.29
Q15   1   0.5706  0.3597  0.5816  11.00000  0.05    0.29
Q16   1   0.8857  0.6980  0.9506  11.00000  0.05    0.29
Q17   1   0.5899  0.5189  0.9806  11.00000  0.05    0.28
Q18   1   0.5613 -0.0007  0.5637  11.00000  0.05    0.28
Q19   1   0.1339  0.4149  0.8035  11.00000  0.05    0.28
Q20   1   0.3417  0.7993  0.5407  11.00000  0.05    0.28
;
_shelx_res_checksum              41748

_chemical_properties_physical    Air-sensitive,Oxygen-sensitive
