# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2007

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Christopher Moody'
'Howard D. Beall'
'Kurtis C. Bray'
'Mary Hassani'
'Jeffrey J. Newsome'
'A. Slawin'
'Elizabeth Swann'

_publ_contact_author_name        'Christopher Moody'
_publ_contact_author_address     
;
School of Chemistry
University of Nottingham
University Park
Nottingham
NG7 2RD
UNITED KINGDOM
;

_publ_contact_author_email       C.J.MOODY@NOTTINGHAM.AC.UK

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Indolequinone Antitumour Agents: Correlation between
Quinone Structure and Rate of Metabolism by Recombinant Human NAD(P)H:
Quinone Oxidoreductase. Part 3
;

data_37
_database_code_depnum_ccdc_archive 'CCDC 639563'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 O4'
_chemical_formula_sum            'C14 H16 N2 O4'
_chemical_formula_weight         276.29

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5254(16)
_cell_length_b                   8.6886(16)
_cell_length_c                   10.3659(19)
_cell_angle_alpha                97.728(3)
_cell_angle_beta                 94.587(2)
_cell_angle_gamma                117.361(3)
_cell_volume                     666.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      12
_cell_measurement_theta_max      28

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.728237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3238
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         23.25
_reflns_number_total             1831
_reflns_number_gt                1193
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.050(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1831
_refine_ls_number_parameters     193
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_restrained_S_all      0.892
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.002

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
N1 N 0.2144(2) 0.5124(2) 0.40412(17) 0.0581(5) Uani 1 1 d . . .
C1 C 0.0737(3) 0.4237(3) 0.2873(2) 0.0759(8) Uani 1 1 d . . .
H1A H -0.0276 0.3261 0.3087 0.114 Uiso 1 1 calc R . .
H1B H 0.1189 0.3812 0.2169 0.114 Uiso 1 1 calc R . .
H1C H 0.0380 0.5059 0.2603 0.114 Uiso 1 1 calc R . .
C2 C 0.3729(3) 0.6672(3) 0.42400(19) 0.0536(6) Uani 1 1 d . . .
C3 C 0.4643(3) 0.6952(3) 0.5508(2) 0.0517(6) Uani 1 1 d . . .
C3A C 0.3547(3) 0.5495(3) 0.60988(19) 0.0495(6) Uani 1 1 d . . .
C4 C 0.3733(3) 0.4989(3) 0.7321(2) 0.0529(6) Uani 1 1 d . . .
N4 N 0.5195(3) 0.5987(3) 0.82940(19) 0.0741(6) Uani 1 1 d D . .
H4A H 0.616(2) 0.7041(19) 0.807(2) 0.092(8) Uiso 1 1 d D . .
H4B H 0.538(4) 0.547(3) 0.9040(17) 0.100(9) Uiso 1 1 d D . .
C5 C 0.2357(3) 0.3418(3) 0.7521(2) 0.0582(6) Uani 1 1 d . . .
O5 O 0.2625(2) 0.3013(2) 0.87431(14) 0.0726(5) Uani 1 1 d . . .
C6 C 0.0852(3) 0.2360(3) 0.6573(2) 0.0670(7) Uani 1 1 d . . .
H6A H -0.0036 0.1317 0.6750 0.080 Uiso 1 1 calc R . .
C7 C 0.0648(3) 0.2821(3) 0.5380(2) 0.0653(7) Uani 1 1 d . . .
H7A H -0.0358 0.2112 0.4743 0.078 Uiso 1 1 calc R . .
C7A C 0.2005(3) 0.4388(3) 0.5167(2) 0.0530(6) Uani 1 1 d . . .
C8 C 0.4335(3) 0.7816(3) 0.3258(2) 0.0627(6) Uani 1 1 d . . .
O8 O 0.5722(3) 0.9179(3) 0.34387(17) 0.0950(6) Uani 1 1 d . . .
O9 O 0.3219(2) 0.7214(2) 0.21352(16) 0.0825(6) Uani 1 1 d . . .
C9 C 0.3739(4) 0.8227(4) 0.1091(2) 0.0825(8) Uani 1 1 d . . .
H9A H 0.4850 0.8316 0.0852 0.099 Uiso 1 1 calc R . .
H9B H 0.3910 0.9410 0.1384 0.099 Uiso 1 1 calc R . .
C10 C 0.2281(4) 0.7288(4) -0.0054(3) 0.0981(10) Uani 1 1 d . . .
H10A H 0.2097 0.6107 -0.0315 0.147 Uiso 1 1 calc R . .
H10B H 0.2601 0.7901 -0.0774 0.147 Uiso 1 1 calc R . .
H10C H 0.1199 0.7247 0.0185 0.147 Uiso 1 1 calc R . .
C11 C 0.6391(3) 0.8425(3) 0.6013(2) 0.0657(7) Uani 1 1 d . . .
H11A H 0.6905 0.9225 0.5464 0.079 Uiso 1 1 calc R . .
O11 O 0.7261(2) 0.8721(2) 0.70991(16) 0.0816(6) Uani 1 1 d . . .
C12 C 0.1507(3) 0.1283(3) 0.8919(3) 0.0853(9) Uani 1 1 d . . .
H12A H 0.0296 0.1081 0.8864 0.128 Uiso 1 1 calc R . .
H12B H 0.1893 0.1139 0.9770 0.128 Uiso 1 1 calc R . .
H12C H 0.1570 0.0450 0.8245 0.128 Uiso 1 1 calc R . .

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
N1 0.0540(11) 0.0616(12) 0.0499(11) 0.0098(9) -0.0009(8) 0.0218(10)
C1 0.0672(15) 0.0814(17) 0.0578(14) 0.0120(12) -0.0109(12) 0.0213(13)
C2 0.0545(13) 0.0549(14) 0.0503(13) 0.0113(10) 0.0069(11) 0.0251(12)
C3 0.0483(13) 0.0511(14) 0.0525(13) 0.0085(10) 0.0053(10) 0.0219(11)
C3A 0.0464(12) 0.0490(13) 0.0485(13) 0.0088(10) 0.0063(10) 0.0193(10)
C4 0.0473(12) 0.0519(13) 0.0499(13) 0.0065(10) 0.0025(10) 0.0175(11)
N4 0.0534(12) 0.0750(15) 0.0611(12) 0.0213(11) -0.0083(10) 0.0039(11)
C5 0.0547(13) 0.0561(14) 0.0536(13) 0.0122(10) 0.0033(11) 0.0183(11)
O5 0.0709(10) 0.0613(11) 0.0598(10) 0.0246(7) -0.0003(8) 0.0084(8)
C6 0.0536(14) 0.0585(15) 0.0674(16) 0.0136(12) -0.0002(12) 0.0099(12)
C7 0.0504(13) 0.0600(15) 0.0620(15) 0.0081(11) -0.0069(11) 0.0102(12)
C7A 0.0498(12) 0.0527(13) 0.0481(13) 0.0081(10) 0.0000(10) 0.0191(11)
C8 0.0666(16) 0.0619(16) 0.0586(15) 0.0127(12) 0.0068(12) 0.0300(14)
O8 0.0961(14) 0.0829(13) 0.0736(12) 0.0317(9) -0.0004(10) 0.0134(12)
O9 0.0802(11) 0.0895(13) 0.0595(10) 0.0286(9) -0.0006(9) 0.0233(10)
C9 0.0928(19) 0.0915(19) 0.0612(15) 0.0353(14) 0.0133(14) 0.0365(16)
C10 0.101(2) 0.122(2) 0.0679(17) 0.0338(16) 0.0047(16) 0.0477(19)
C11 0.0572(14) 0.0619(15) 0.0619(15) 0.0193(11) 0.0094(13) 0.0131(12)
O11 0.0596(10) 0.0765(12) 0.0685(11) 0.0211(8) -0.0090(9) 0.0000(9)
C12 0.0700(16) 0.0782(19) 0.0844(18) 0.0380(14) 0.0048(14) 0.0112(14)

_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
N1 C2 1.374(3) . ?
N1 C7A 1.392(3) . ?
N1 C1 1.471(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.404(3) . ?
C2 C8 1.475(3) . ?
C3 C11 1.441(3) . ?
C3 C3A 1.436(3) . ?
C3A C7A 1.404(3) . ?
C3A C4 1.416(3) . ?
C4 N4 1.376(3) . ?
C4 C5 1.387(3) . ?
N4 H4A 0.9799(11) . ?
N4 H4B 0.9799(11) . ?
C5 C6 1.389(3) . ?
C5 O5 1.389(3) . ?
O5 C12 1.409(3) . ?
C6 C7 1.372(3) . ?
C6 H6A 0.9300 . ?
C7 C7A 1.384(3) . ?
C7 H7A 0.9300 . ?
C8 O8 1.206(3) . ?
C8 O9 1.317(3) . ?
O9 C9 1.455(3) . ?
C9 C10 1.480(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O11 1.223(3) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C2 N1 C7A 109.13(16) . . ?
C2 N1 C1 129.86(19) . . ?
C7A N1 C1 121.01(19) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 108.71(18) . . ?
N1 C2 C8 124.46(19) . . ?
C3 C2 C8 126.83(19) . . ?
C2 C3 C11 123.1(2) . . ?
C2 C3 C3A 107.04(16) . . ?
C11 C3 C3A 129.84(19) . . ?
C7A C3A C4 118.64(19) . . ?
C7A C3A C3 106.80(17) . . ?
C4 C3A C3 134.54(18) . . ?
N4 C4 C5 119.93(19) . . ?
N4 C4 C3A 122.8(2) . . ?
C5 C4 C3A 117.28(17) . . ?
C4 N4 H4A 116.2(14) . . ?
C4 N4 H4B 119.5(17) . . ?
H4A N4 H4B 122(2) . . ?
C4 C5 C6 122.3(2) . . ?
C4 C5 O5 114.08(17) . . ?
C6 C5 O5 123.6(2) . . ?
C5 O5 C12 117.53(16) . . ?
C7 C6 C5 121.4(2) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C7A 117.01(19) . . ?
C6 C7 H7A 121.5 . . ?
C7A C7 H7A 121.5 . . ?
C7 C7A N1 128.29(18) . . ?
C7 C7A C3A 123.36(19) . . ?
N1 C7A C3A 108.33(19) . . ?
O8 C8 O9 121.8(2) . . ?
O8 C8 C2 124.3(2) . . ?
O9 C8 C2 113.9(2) . . ?
C8 O9 C9 117.7(2) . . ?
O9 C9 C10 107.3(2) . . ?
O9 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O9 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O11 C11 C3 125.9(2) . . ?
O11 C11 H11A 117.0 . . ?
C3 C11 H11A 117.0 . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C7A N1 C2 C3 0.2(2) . . . . ?
C1 N1 C2 C3 -178.7(2) . . . . ?
C7A N1 C2 C8 179.9(2) . . . . ?
C1 N1 C2 C8 1.0(4) . . . . ?
N1 C2 C3 C11 177.4(2) . . . . ?
C8 C2 C3 C11 -2.3(3) . . . . ?
N1 C2 C3 C3A 0.0(2) . . . . ?
C8 C2 C3 C3A -179.7(2) . . . . ?
C2 C3 C3A C7A -0.2(2) . . . . ?
C11 C3 C3A C7A -177.3(2) . . . . ?
C2 C3 C3A C4 178.1(2) . . . . ?
C11 C3 C3A C4 0.9(4) . . . . ?
C7A C3A C4 N4 -180.0(2) . . . . ?
C3 C3A C4 N4 1.9(4) . . . . ?
C7A C3A C4 C5 -0.3(3) . . . . ?
C3 C3A C4 C5 -178.5(2) . . . . ?
N4 C4 C5 C6 -180.0(2) . . . . ?
C3A C4 C5 C6 0.4(3) . . . . ?
N4 C4 C5 O5 0.1(3) . . . . ?
C3A C4 C5 O5 -179.60(18) . . . . ?
C4 C5 O5 C12 -166.5(2) . . . . ?
C6 C5 O5 C12 13.6(3) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
O5 C5 C6 C7 179.9(2) . . . . ?
C5 C6 C7 C7A -0.2(4) . . . . ?
C6 C7 C7A N1 178.2(2) . . . . ?
C6 C7 C7A C3A 0.2(3) . . . . ?
C2 N1 C7A C7 -178.6(2) . . . . ?
C1 N1 C7A C7 0.4(4) . . . . ?
C2 N1 C7A C3A -0.3(2) . . . . ?
C1 N1 C7A C3A 178.68(18) . . . . ?
C4 C3A C7A C7 0.1(3) . . . . ?
C3 C3A C7A C7 178.7(2) . . . . ?
C4 C3A C7A N1 -178.26(19) . . . . ?
C3 C3A C7A N1 0.3(2) . . . . ?
N1 C2 C8 O8 179.6(2) . . . . ?
C3 C2 C8 O8 -0.8(4) . . . . ?
N1 C2 C8 O9 -0.8(3) . . . . ?
C3 C2 C8 O9 178.8(2) . . . . ?
O8 C8 O9 C9 1.8(4) . . . . ?
C2 C8 O9 C9 -177.9(2) . . . . ?
C8 O9 C9 C10 180.0(2) . . . . ?
C2 C3 C11 O11 -178.8(2) . . . . ?
C3A C3 C11 O11 -2.0(4) . . . . ?

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
N4 H4A O11 0.9799(11) 1.823(10) 2.752(3) 157(2) .
N4 H4B O5 0.9799(11) 2.30(3) 2.641(3) 99.4(17) .
N4 H4B O5 0.9799(11) 2.53(2) 3.245(2) 130(2) 2_667

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.102
_refine_diff_density_rms         0.027