# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Chemical Science'
_journal_coden_cambridge         1475
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Mohammad Movassaghi'
_publ_contact_author_email       movassag@MIT.EDU
loop_
_publ_author_name
N.Boyer
M.Movassaghi

data_x8_11110
_database_code_depnum_ccdc_archive 'CCDC 866659'
#TrackingRef '05-GlioB.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N4 O2 S2'
_chemical_formula_weight         464.59
_chemical_absolute_configuration rmad

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.5206(13)
_cell_length_b                   13.968(2)
_cell_length_c                   18.439(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2194.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9049
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      30.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9349
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
'Bruker three-circle diffractometer, Bruker APEX CCD'
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28691
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         29.80
_reflns_number_total             6251
_reflns_number_gt                5833
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0393P)^2^+0.5995P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_number_reflns         6251
_refine_ls_number_parameters     298
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.88471(4) 0.28061(2) 0.134122(19) 0.01463(8) Uani 1 1 d . . .
S2 S 1.11876(5) 0.42327(3) 0.02642(2) 0.01935(8) Uani 1 1 d . . .
O1 O 1.22916(14) 0.16801(8) 0.17283(6) 0.0186(2) Uani 1 1 d . . .
O2 O 1.17571(13) 0.54303(7) 0.18553(6) 0.0182(2) Uani 1 1 d . . .
N1 N 0.84976(15) 0.48636(9) 0.26258(7) 0.0151(2) Uani 1 1 d D . .
H1N H 0.849(2) 0.5478(11) 0.2734(10) 0.018 Uiso 1 1 d D . .
C2 C 0.98887(16) 0.43063(10) 0.27868(8) 0.0121(3) Uani 1 1 d . . .
H2 H 1.0620 0.4667 0.3111 0.015 Uiso 1 1 calc R . .
C3 C 0.93326(17) 0.33462(10) 0.31510(8) 0.0118(3) Uani 1 1 d . . .
C4 C 0.75639(17) 0.34009(11) 0.30189(8) 0.0130(3) Uani 1 1 d . . .
C5 C 0.64166(18) 0.27307(11) 0.31660(8) 0.0172(3) Uani 1 1 d . . .
H5 H 0.6688 0.2098 0.3307 0.021 Uiso 1 1 calc R . .
C6 C 0.48393(19) 0.30070(13) 0.31018(9) 0.0223(3) Uani 1 1 d . . .
H6 H 0.4029 0.2557 0.3196 0.027 Uiso 1 1 calc R . .
C7 C 0.44588(19) 0.39416(13) 0.29005(9) 0.0220(3) Uani 1 1 d . . .
H7 H 0.3386 0.4126 0.2881 0.026 Uiso 1 1 calc R . .
C8 C 0.56031(18) 0.46079(12) 0.27280(8) 0.0185(3) Uani 1 1 d . . .
H8 H 0.5333 0.5238 0.2580 0.022 Uiso 1 1 calc R . .
C9 C 0.71674(17) 0.43206(11) 0.27800(8) 0.0143(3) Uani 1 1 d . . .
N10 N 1.06948(15) 0.39785(9) 0.21225(6) 0.0129(2) Uani 1 1 d . . .
C11 C 1.05104(17) 0.29605(10) 0.19800(8) 0.0122(3) Uani 1 1 d . . .
C12 C 1.02018(16) 0.25471(10) 0.27373(8) 0.0122(3) Uani 1 1 d . . .
H12A H 1.1201 0.2384 0.2982 0.015 Uiso 1 1 calc R . .
H12B H 0.9546 0.1963 0.2706 0.015 Uiso 1 1 calc R . .
C13 C 1.19658(17) 0.25300(11) 0.16276(8) 0.0139(3) Uani 1 1 d . . .
N14 N 1.28378(15) 0.31183(9) 0.12094(7) 0.0155(2) Uani 1 1 d . . .
C15 C 1.24268(17) 0.41149(11) 0.10820(8) 0.0152(3) Uani 1 1 d . . .
H15 H 1.3421 0.4477 0.0994 0.018 Uiso 1 1 calc R . .
C16 C 1.15967(17) 0.45771(10) 0.17195(8) 0.0141(3) Uani 1 1 d . . .
C17 C 1.42151(19) 0.27436(12) 0.08244(10) 0.0227(3) Uani 1 1 d . . .
H17A H 1.4296 0.2052 0.0906 0.034 Uiso 1 1 calc R . .
H17B H 1.5164 0.3060 0.1006 0.034 Uiso 1 1 calc R . .
H17C H 1.4105 0.2869 0.0304 0.034 Uiso 1 1 calc R . .
C18 C 1.1765(2) 0.54001(13) -0.00547(11) 0.0320(4) Uani 1 1 d . . .
H18A H 1.1641 0.5868 0.0337 0.048 Uiso 1 1 calc R . .
H18B H 1.1103 0.5585 -0.0466 0.048 Uiso 1 1 calc R . .
H18C H 1.2866 0.5383 -0.0209 0.048 Uiso 1 1 calc R . .
C19 C 0.8485(2) 0.15363(11) 0.13902(10) 0.0230(3) Uani 1 1 d . . .
H19A H 0.9455 0.1188 0.1281 0.034 Uiso 1 1 calc R . .
H19B H 0.7676 0.1361 0.1037 0.034 Uiso 1 1 calc R . .
H19C H 0.8126 0.1369 0.1879 0.034 Uiso 1 1 calc R . .
N1' N 1.03657(18) 0.27646(10) 0.50650(7) 0.0212(3) Uani 1 1 d D . .
H1'N H 1.072(2) 0.2393(13) 0.5390(10) 0.025 Uiso 1 1 d D . .
C2' C 1.04145(19) 0.25862(11) 0.43297(8) 0.0178(3) Uani 1 1 d . . .
H2' H 1.0915 0.2052 0.4111 0.021 Uiso 1 1 calc R . .
C3' C 0.96320(17) 0.32960(10) 0.39598(8) 0.0132(3) Uani 1 1 d . . .
C4' C 0.90595(17) 0.39575(11) 0.45033(8) 0.0142(3) Uani 1 1 d . . .
C5' C 0.82246(18) 0.48301(11) 0.44754(9) 0.0168(3) Uani 1 1 d . . .
H5' H 0.7888 0.5086 0.4024 0.020 Uiso 1 1 calc R . .
C6' C 0.79055(19) 0.53060(12) 0.51154(9) 0.0208(3) Uani 1 1 d . . .
H6' H 0.7357 0.5898 0.5099 0.025 Uiso 1 1 calc R . .
C7' C 0.8377(2) 0.49320(12) 0.57927(9) 0.0211(3) Uani 1 1 d . . .
H7' H 0.8117 0.5267 0.6225 0.025 Uiso 1 1 calc R . .
C8' C 0.92090(19) 0.40868(12) 0.58364(8) 0.0198(3) Uani 1 1 d . . .
H8' H 0.9545 0.3840 0.6291 0.024 Uiso 1 1 calc R . .
C9' C 0.95435(18) 0.36027(11) 0.51873(8) 0.0163(3) 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
S1 0.01563(15) 0.01497(15) 0.01330(15) 0.00007(13) -0.00208(13) -0.00056(13)
S2 0.02188(17) 0.02182(18) 0.01435(16) 0.00195(14) 0.00040(15) -0.00257(15)
O1 0.0199(5) 0.0134(5) 0.0225(6) 0.0002(4) 0.0043(5) 0.0022(4)
O2 0.0223(5) 0.0123(5) 0.0200(5) -0.0001(4) 0.0036(4) -0.0017(4)
N1 0.0143(6) 0.0137(5) 0.0174(6) 0.0008(5) 0.0029(5) 0.0023(4)
C2 0.0131(6) 0.0120(6) 0.0113(6) -0.0010(5) 0.0015(5) 0.0002(5)
C3 0.0124(6) 0.0131(6) 0.0100(6) -0.0004(5) 0.0002(5) 0.0014(5)
C4 0.0135(6) 0.0159(7) 0.0098(6) -0.0005(5) 0.0001(5) 0.0011(5)
C5 0.0162(7) 0.0193(7) 0.0162(6) 0.0016(6) -0.0002(5) -0.0006(6)
C6 0.0137(7) 0.0304(9) 0.0226(8) 0.0040(7) -0.0005(6) -0.0037(6)
C7 0.0144(7) 0.0334(9) 0.0183(7) 0.0034(7) -0.0027(6) 0.0035(6)
C8 0.0189(7) 0.0219(7) 0.0146(7) 0.0030(6) -0.0006(6) 0.0064(6)
C9 0.0154(6) 0.0175(7) 0.0099(6) 0.0005(5) 0.0002(5) 0.0012(5)
N10 0.0154(5) 0.0114(5) 0.0119(5) -0.0018(4) 0.0025(5) 0.0000(4)
C11 0.0128(6) 0.0124(6) 0.0113(6) -0.0018(5) 0.0004(5) -0.0002(5)
C12 0.0135(6) 0.0128(6) 0.0104(6) 0.0000(5) -0.0002(5) 0.0011(5)
C13 0.0139(6) 0.0146(6) 0.0130(6) -0.0028(5) -0.0006(5) -0.0002(5)
N14 0.0157(6) 0.0137(6) 0.0170(6) -0.0013(5) 0.0050(5) 0.0020(5)
C15 0.0167(6) 0.0138(7) 0.0151(6) 0.0000(5) 0.0026(5) -0.0019(5)
C16 0.0141(6) 0.0147(6) 0.0136(6) 0.0007(5) -0.0008(5) 0.0004(5)
C17 0.0192(7) 0.0206(8) 0.0282(8) -0.0007(7) 0.0114(6) 0.0027(6)
C18 0.0414(10) 0.0241(8) 0.0304(9) 0.0108(7) -0.0041(8) -0.0056(8)
C19 0.0286(8) 0.0158(7) 0.0246(8) -0.0006(6) -0.0085(7) -0.0064(6)
N1' 0.0312(7) 0.0191(6) 0.0133(6) 0.0016(5) -0.0038(5) 0.0073(6)
C2' 0.0243(7) 0.0156(7) 0.0133(7) -0.0022(5) -0.0024(6) 0.0045(6)
C3' 0.0132(6) 0.0143(7) 0.0122(6) 0.0000(5) -0.0010(5) -0.0007(5)
C4' 0.0143(6) 0.0165(6) 0.0117(6) -0.0001(5) -0.0001(5) -0.0006(5)
C5' 0.0175(7) 0.0186(7) 0.0143(7) 0.0000(6) -0.0014(6) 0.0026(6)
C6' 0.0212(7) 0.0208(8) 0.0203(8) -0.0044(6) -0.0018(6) 0.0062(6)
C7' 0.0246(8) 0.0240(8) 0.0147(7) -0.0063(6) 0.0012(6) 0.0018(6)
C8' 0.0257(8) 0.0226(8) 0.0111(6) -0.0003(6) -0.0029(6) 0.0004(6)
C9' 0.0181(7) 0.0171(7) 0.0138(7) -0.0002(6) -0.0006(6) 0.0012(5)

_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 C19 1.8026(16) . ?
S1 C11 1.8553(15) . ?
S2 C18 1.8019(19) . ?
S2 C15 1.8481(16) . ?
O1 C13 1.2332(19) . ?
O2 C16 1.2255(18) . ?
N1 C9 1.3932(19) . ?
N1 C2 1.4488(18) . ?
C2 N10 1.4771(18) . ?
C2 C3 1.573(2) . ?
C3 C3' 1.515(2) . ?
C3 C4 1.529(2) . ?
C3 C12 1.5415(19) . ?
C4 C5 1.380(2) . ?
C4 C9 1.399(2) . ?
C5 C6 1.403(2) . ?
C6 C7 1.395(2) . ?
C7 C8 1.385(2) . ?
C8 C9 1.395(2) . ?
N10 C16 1.3570(19) . ?
N10 C11 1.4546(18) . ?
C11 C13 1.524(2) . ?
C11 C12 1.534(2) . ?
C13 N14 1.3499(19) . ?
N14 C15 1.4545(19) . ?
N14 C17 1.4680(19) . ?
C15 C16 1.516(2) . ?
N1' C2' 1.379(2) . ?
N1' C9' 1.383(2) . ?
C2' C3' 1.376(2) . ?
C3' C4' 1.448(2) . ?
C4' C5' 1.412(2) . ?
C4' C9' 1.417(2) . ?
C5' C6' 1.381(2) . ?
C6' C7' 1.412(2) . ?
C7' C8' 1.380(2) . ?
C8' C9' 1.404(2) . ?

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
C19 S1 C11 102.32(7) . . ?
C18 S2 C15 101.00(8) . . ?
C9 N1 C2 109.34(12) . . ?
N1 C2 N10 112.14(12) . . ?
N1 C2 C3 107.41(11) . . ?
N10 C2 C3 103.29(11) . . ?
C3' C3 C4 108.98(12) . . ?
C3' C3 C12 111.89(12) . . ?
C4 C3 C12 115.53(12) . . ?
C3' C3 C2 114.15(12) . . ?
C4 C3 C2 100.74(11) . . ?
C12 C3 C2 105.15(11) . . ?
C5 C4 C9 120.89(13) . . ?
C5 C4 C3 129.28(13) . . ?
C9 C4 C3 109.51(12) . . ?
C4 C5 C6 118.37(14) . . ?
C7 C6 C5 120.15(15) . . ?
C8 C7 C6 121.75(15) . . ?
C7 C8 C9 117.61(15) . . ?
N1 C9 C8 127.34(14) . . ?
N1 C9 C4 111.57(13) . . ?
C8 C9 C4 121.08(14) . . ?
C16 N10 C11 124.37(12) . . ?
C16 N10 C2 121.77(12) . . ?
C11 N10 C2 113.74(11) . . ?
N10 C11 C13 112.02(12) . . ?
N10 C11 C12 102.83(11) . . ?
C13 C11 C12 112.28(12) . . ?
N10 C11 S1 108.11(10) . . ?
C13 C11 S1 107.77(10) . . ?
C12 C11 S1 113.78(10) . . ?
C11 C12 C3 105.09(11) . . ?
O1 C13 N14 123.23(14) . . ?
O1 C13 C11 119.94(13) . . ?
N14 C13 C11 116.83(13) . . ?
C13 N14 C15 122.84(12) . . ?
C13 N14 C17 119.95(13) . . ?
C15 N14 C17 117.10(13) . . ?
N14 C15 C16 113.24(12) . . ?
N14 C15 S2 110.77(10) . . ?
C16 C15 S2 109.16(10) . . ?
O2 C16 N10 123.40(14) . . ?
O2 C16 C15 121.36(13) . . ?
N10 C16 C15 115.24(12) . . ?
C2' N1' C9' 109.18(13) . . ?
C3' C2' N1' 110.04(13) . . ?
C2' C3' C4' 106.26(13) . . ?
C2' C3' C3 127.10(13) . . ?
C4' C3' C3 126.53(13) . . ?
C5' C4' C9' 118.75(13) . . ?
C5' C4' C3' 134.05(14) . . ?
C9' C4' C3' 107.16(13) . . ?
C6' C5' C4' 118.90(14) . . ?
C5' C6' C7' 121.44(15) . . ?
C8' C7' C6' 120.96(14) . . ?
C7' C8' C9' 117.82(14) . . ?
N1' C9' C8' 130.52(14) . . ?
N1' C9' C4' 107.36(13) . . ?
C8' C9' C4' 122.10(14) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.80
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.049