# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Show-Jen Chiou.'
'Han-Hun Chang.'
'Yun-Lung Ho.'
'Hung-Jen Huang.'
'Wei-Ning Huang.'
'Yu-Der Wen.'

_publ_contact_author_name        'Show-Jen Chiou'
_publ_contact_author_email       GENECHIOU@MAIL.NCYU.EDU.TW

_publ_section_title              
;
The Water-Soluble Roussin's Red Ester Acting
as the Potential Photochemical NO-delivery agent:
Photolysis Reactions, DNA Cleavage and Anticancer Activity
;

# Attachment '8246.cif'

data_8246
_database_code_depnum_ccdc_archive 'CCDC 719803'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H25 O3 P1 S1'
_chemical_formula_sum            'C23 H25 O3 P S'
_chemical_formula_weight         412.46

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.00660(10)
_cell_length_b                   34.1821(7)
_cell_length_c                   9.0994(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.9130(10)
_cell_angle_gamma                90.00
_cell_volume                     2007.35(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    17310
_cell_measurement_theta_min      2.037
_cell_measurement_theta_max      25.35

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9211
_exptl_absorpt_correction_T_max  1.018
_exptl_absorpt_process_details   
;
?
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14233
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3677
_reflns_number_gt                2820
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.0775P)^2^+0.9187P] 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    fixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3677
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.77444(12) 0.14880(2) 0.85480(9) 0.0281(3) Uani 1 1 d . . .
P1 P 0.85035(13) 0.22433(2) 0.59861(9) 0.0274(3) Uani 1 1 d . . .
O1 O 0.5911(4) 0.27854(7) 0.6183(3) 0.0420(6) Uani 1 1 d . . .
H1' H 0.4696 0.2759 0.6298 0.050 Uiso 1 1 d R . .
O2 O 1.2203(3) 0.26448(7) 0.6800(3) 0.0384(6) Uani 1 1 d . . .
H2' H 1.2092 0.2760 0.7591 0.046 Uiso 1 1 d R . .
O3 O 0.6955(4) 0.20876(7) 0.4442(2) 0.0354(6) Uani 1 1 d . . .
C1 C 0.7249(5) 0.24897(9) 0.7136(4) 0.0325(7) Uani 1 1 d . . .
H1A H 0.6459 0.2303 0.7470 0.039 Uiso 1 1 calc R . .
H1B H 0.8287 0.2606 0.8083 0.039 Uiso 1 1 calc R . .
C2 C 1.0228(5) 0.25901(11) 0.5592(4) 0.0382(8) Uani 1 1 d . . .
H2A H 1.0408 0.2505 0.4637 0.046 Uiso 1 1 calc R . .
H2B H 0.9538 0.2842 0.5357 0.046 Uiso 1 1 calc R . .
C3 C 1.0169(5) 0.18758(9) 0.7263(4) 0.0297(7) Uani 1 1 d . . .
H3A H 1.1337 0.1837 0.6960 0.036 Uiso 1 1 calc R . .
H3B H 1.0707 0.1972 0.8352 0.036 Uiso 1 1 calc R . .
C4 C 0.9114(5) 0.14793(9) 0.7215(4) 0.0305(7) Uani 1 1 d . . .
H4A H 1.0149 0.1273 0.7537 0.037 Uiso 1 1 calc R . .
H4B H 0.8147 0.1425 0.6135 0.037 Uiso 1 1 calc R . .
C5 C 0.6054(5) 0.10471(8) 0.7932(3) 0.0257(7) Uani 1 1 d . . .
C6 C 0.4050(5) 0.11231(9) 0.6456(3) 0.0251(7) Uani 1 1 d . . .
C7 C 0.3775(5) 0.14409(9) 0.5438(4) 0.0316(7) Uani 1 1 d . . .
H7 H 0.4832 0.1623 0.5647 0.038 Uiso 1 1 calc R . .
C8 C 0.1932(5) 0.14885(10) 0.4111(4) 0.0357(8) Uani 1 1 d . . .
H8 H 0.1775 0.1703 0.3444 0.043 Uiso 1 1 calc R . .
C9 C 0.0335(5) 0.12227(11) 0.3770(4) 0.0391(9) Uani 1 1 d . . .
H9 H -0.0895 0.1256 0.2884 0.047 Uiso 1 1 calc R . .
C10 C 0.0596(5) 0.09058(10) 0.4769(4) 0.0350(8) Uani 1 1 d . . .
H10 H -0.0461 0.0723 0.4546 0.042 Uiso 1 1 calc R . .
C11 C 0.2410(5) 0.08578(9) 0.6096(4) 0.0306(7) Uani 1 1 d . . .
H11 H 0.2545 0.0645 0.6765 0.037 Uiso 1 1 calc R . .
C12 C 0.7314(5) 0.07053(9) 0.7673(4) 0.0257(7) Uani 1 1 d . . .
C13 C 0.6628(5) 0.04800(9) 0.6297(4) 0.0311(7) Uani 1 1 d . . .
H13 H 0.5378 0.0541 0.5470 0.037 Uiso 1 1 calc R . .
C14 C 0.7773(6) 0.01648(10) 0.6132(4) 0.0375(8) Uani 1 1 d . . .
H14 H 0.7275 0.0017 0.5202 0.045 Uiso 1 1 calc R . .
C15 C 0.9635(5) 0.00685(10) 0.7328(4) 0.0389(8) Uani 1 1 d . . .
H15 H 1.0387 -0.0146 0.7223 0.047 Uiso 1 1 calc R . .
C16 C 1.0372(5) 0.02965(10) 0.8693(4) 0.0362(8) Uani 1 1 d . . .
H16 H 1.1641 0.0237 0.9503 0.043 Uiso 1 1 calc R . .
C17 C 0.9238(5) 0.06103(9) 0.8859(4) 0.0299(7) Uani 1 1 d . . .
H17 H 0.9763 0.0762 0.9779 0.036 Uiso 1 1 calc R . .
C18 C 0.5473(5) 0.09806(9) 0.9386(3) 0.0264(7) Uani 1 1 d . . .
C19 C 0.5829(5) 0.06318(9) 1.0243(4) 0.0323(7) Uani 1 1 d . . .
H19 H 0.6450 0.0422 0.9948 0.039 Uiso 1 1 calc R . .
C20 C 0.5258(5) 0.05965(11) 1.1543(4) 0.0405(9) Uani 1 1 d . . .
H20 H 0.5512 0.0363 1.2113 0.049 Uiso 1 1 calc R . .
C21 C 0.4324(6) 0.09008(11) 1.1994(4) 0.0422(9) Uani 1 1 d . . .
H21 H 0.3945 0.0874 1.2861 0.051 Uiso 1 1 calc R . .
C22 C 0.3952(6) 0.12484(11) 1.1145(4) 0.0420(9) Uani 1 1 d . . .
H22 H 0.3333 0.1457 1.1445 0.050 Uiso 1 1 calc R . .
C23 C 0.4503(5) 0.12838(10) 0.9853(4) 0.0333(8) Uani 1 1 d . . .
H23 H 0.4221 0.1516 0.9278 0.040 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
S1 0.0298(5) 0.0262(4) 0.0308(4) -0.0024(3) 0.0144(3) -0.0016(3)
P1 0.0261(5) 0.0303(5) 0.0253(4) 0.0016(3) 0.0096(3) -0.0007(3)
O1 0.0389(14) 0.0409(14) 0.0476(15) 0.0090(11) 0.0183(12) 0.0121(11)
O2 0.0316(13) 0.0499(15) 0.0323(12) -0.0039(11) 0.0108(10) -0.0053(11)
O3 0.0335(13) 0.0425(13) 0.0253(11) -0.0005(10) 0.0060(10) -0.0039(11)
C1 0.0330(18) 0.0307(17) 0.0336(18) 0.0030(14) 0.0127(15) 0.0058(14)
C2 0.038(2) 0.046(2) 0.0277(17) 0.0051(15) 0.0090(15) -0.0064(16)
C3 0.0241(16) 0.0348(17) 0.0326(17) 0.0016(14) 0.0135(13) -0.0014(14)
C4 0.0280(17) 0.0308(17) 0.0347(17) 0.0002(14) 0.0144(14) 0.0019(14)
C5 0.0261(16) 0.0240(15) 0.0278(16) 0.0022(13) 0.0113(13) 0.0008(13)
C6 0.0252(16) 0.0279(16) 0.0249(15) -0.0012(13) 0.0125(13) 0.0041(13)
C7 0.0336(18) 0.0312(17) 0.0336(17) 0.0014(14) 0.0169(15) 0.0020(14)
C8 0.0369(19) 0.041(2) 0.0278(17) 0.0067(15) 0.0105(15) 0.0100(16)
C9 0.0304(19) 0.056(2) 0.0281(18) -0.0026(16) 0.0079(14) 0.0093(17)
C10 0.0276(17) 0.040(2) 0.0383(18) -0.0086(16) 0.0144(15) -0.0030(15)
C11 0.0310(17) 0.0316(17) 0.0310(17) 0.0012(14) 0.0140(14) 0.0010(14)
C12 0.0266(16) 0.0233(15) 0.0300(16) 0.0051(13) 0.0139(13) 0.0018(13)
C13 0.0299(17) 0.0319(17) 0.0312(17) 0.0011(14) 0.0117(14) 0.0044(14)
C14 0.045(2) 0.0321(18) 0.0391(19) -0.0050(15) 0.0210(17) 0.0032(16)
C15 0.038(2) 0.0289(18) 0.055(2) 0.0052(16) 0.0237(18) 0.0095(15)
C16 0.0286(18) 0.0318(18) 0.048(2) 0.0071(16) 0.0151(15) 0.0068(15)
C17 0.0283(17) 0.0288(17) 0.0313(17) 0.0002(14) 0.0102(14) -0.0003(14)
C18 0.0220(15) 0.0303(16) 0.0267(15) 0.0002(13) 0.0093(13) 0.0007(13)
C19 0.0335(18) 0.0312(18) 0.0346(18) 0.0064(14) 0.0161(15) 0.0054(15)
C20 0.041(2) 0.045(2) 0.0346(18) 0.0135(16) 0.0128(16) 0.0029(17)
C21 0.041(2) 0.061(2) 0.0280(17) 0.0058(17) 0.0170(15) 0.0039(18)
C22 0.046(2) 0.046(2) 0.041(2) -0.0025(16) 0.0244(17) 0.0071(17)
C23 0.0338(19) 0.0343(18) 0.0327(17) 0.0035(14) 0.0140(15) 0.0053(15)

_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
S1 C4 1.816(3) . ?
S1 C5 1.863(3) . ?
P1 O3 1.499(2) . ?
P1 C3 1.798(3) . ?
P1 C1 1.814(3) . ?
P1 C2 1.825(3) . ?
O1 C1 1.421(4) . ?
O1 H1' 0.9016 . ?
O2 C2 1.405(4) . ?
O2 H2' 0.8499 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.536(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C12 1.537(4) . ?
C5 C18 1.545(4) . ?
C5 C6 1.541(4) . ?
C6 C7 1.391(4) . ?
C6 C11 1.399(4) . ?
C7 C8 1.392(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.386(4) . ?
C12 C17 1.398(4) . ?
C13 C14 1.385(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.393(4) . ?
C18 C19 1.393(4) . ?
C19 C20 1.394(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9300 . ?
C23 H23 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
C4 S1 C5 103.00(14) . . ?
O3 P1 C3 114.09(14) . . ?
O3 P1 C1 111.64(15) . . ?
C3 P1 C1 106.84(14) . . ?
O3 P1 C2 109.85(14) . . ?
C3 P1 C2 105.55(15) . . ?
C1 P1 C2 108.55(16) . . ?
C1 O1 H1' 106.7 . . ?
C2 O2 H2' 109.7 . . ?
O1 C1 P1 109.3(2) . . ?
O1 C1 H1A 109.8 . . ?
P1 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
P1 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
O2 C2 P1 117.3(2) . . ?
O2 C2 H2A 108.0 . . ?
P1 C2 H2A 108.0 . . ?
O2 C2 H2B 108.0 . . ?
P1 C2 H2B 108.0 . . ?
H2A C2 H2B 107.2 . . ?
C4 C3 P1 114.5(2) . . ?
C4 C3 H3A 108.6 . . ?
P1 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
P1 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 S1 109.9(2) . . ?
C3 C4 H4A 109.7 . . ?
S1 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
S1 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C12 C5 C18 112.2(2) . . ?
C12 C5 C6 112.2(2) . . ?
C18 C5 C6 108.4(2) . . ?
C12 C5 S1 109.0(2) . . ?
C18 C5 S1 102.12(19) . . ?
C6 C5 S1 112.5(2) . . ?
C7 C6 C11 117.5(3) . . ?
C7 C6 C5 123.7(3) . . ?
C11 C6 C5 118.8(3) . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 118.8(3) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C6 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C13 C12 C17 117.3(3) . . ?
C13 C12 C5 122.9(3) . . ?
C17 C12 C5 119.8(3) . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 118.9(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 121.3(3) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
C23 C18 C19 117.9(3) . . ?
C23 C18 C5 118.3(3) . . ?
C19 C18 C5 123.8(3) . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C18 121.8(3) . . ?
C22 C23 H23 119.1 . . ?
C18 C23 H23 119.1 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.141