# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p2
#TrackingRef 'p2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 N5 O2 S'
_chemical_formula_weight         399.51

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           ?
_symmetry_space_group_name_H-M   'P 21 21 21'

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                   8.7524(4)
_cell_length_b                   15.1376(7)
_cell_length_c                   15.8697(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2102.58(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5437
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3517
_reflns_number_gt                3201
_reflns_threshold_expression     >2sigma(I)

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

_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^)+(0.1000P)^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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_number_reflns         3517
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_restrained_S_all      0.814
_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 0.46172(8) 0.97282(4) 1.06929(4) 0.0426(2) Uani 1 1 d . . .
O1 O 0.56008(16) 0.73368(11) 0.92908(10) 0.0323(4) Uani 1 1 d . . .
O2 O 0.14489(17) 0.74067(11) 0.83820(10) 0.0328(4) Uani 1 1 d . . .
N2 N 0.39152(19) 0.80723(13) 1.05293(12) 0.0283(4) Uani 1 1 d . . .
H2A H 0.4328 0.8014 1.1018 0.034 Uiso 1 1 calc R . .
C14 C 0.3692(2) 0.62522(15) 0.89455(13) 0.0261(5) Uani 1 1 d . . .
H14A H 0.2696 0.6084 0.9177 0.031 Uiso 1 1 calc R . .
N3 N 0.3473(2) 0.73219(12) 1.00910(11) 0.0256(4) Uani 1 1 d . . .
H3A H 0.2642 0.7052 1.0224 0.031 Uiso 1 1 calc R . .
N1 N 0.27585(19) 0.89509(12) 0.95464(12) 0.0273(4) Uani 1 1 d . . .
H1A H 0.2348 0.8457 0.9403 0.033 Uiso 1 1 calc R . .
N4 N 0.3501(2) 0.65578(13) 0.80864(11) 0.0281(4) Uani 1 1 d . . .
H4A H 0.4120 0.6372 0.7705 0.034 Uiso 1 1 calc R . .
C1 C 0.2312(2) 0.96856(15) 0.90426(14) 0.0278(5) Uani 1 1 d . . .
C16 C 0.4349(2) 0.70168(15) 0.94562(13) 0.0244(4) Uani 1 1 d . . .
C13 C 0.4772(3) 0.54552(16) 0.89743(15) 0.0319(5) Uani 1 1 d . . .
H13A H 0.5777 0.5634 0.8783 0.038 Uiso 1 1 calc R . .
H13B H 0.4866 0.5252 0.9552 0.038 Uiso 1 1 calc R . .
C15 C 0.3715(2) 0.89001(15) 1.02085(13) 0.0267(5) Uani 1 1 d . . .
C6 C 0.1149(2) 0.95265(16) 0.84648(15) 0.0334(5) Uani 1 1 d . . .
H6A H 0.0662 0.8981 0.8458 0.040 Uiso 1 1 calc R . .
C12 C 0.4205(2) 0.47076(15) 0.84315(14) 0.0293(5) Uani 1 1 d . . .
C11 C 0.2923(3) 0.42201(16) 0.86669(16) 0.0344(6) Uani 1 1 d . . .
H11A H 0.2446 0.4337 0.9178 0.041 Uiso 1 1 calc R . .
C4 C 0.1415(3) 1.09901(18) 0.79106(17) 0.0426(6) Uani 1 1 d . . .
H4B H 0.1122 1.1425 0.7530 0.051 Uiso 1 1 calc R . .
C17 C 0.2391(2) 0.71181(15) 0.78699(14) 0.0277(5) Uani 1 1 d . . .
N5 N 0.3366(2) 0.69056(16) 0.64125(12) 0.0390(5) Uani 1 1 d . . .
C18 C 0.2376(3) 0.74222(18) 0.69678(15) 0.0363(6) Uani 1 1 d . . .
H18A H 0.1337 0.7391 0.6757 0.044 Uiso 1 1 calc R . .
H18B H 0.2694 0.8036 0.6948 0.044 Uiso 1 1 calc R . .
C5 C 0.0716(3) 1.01698(18) 0.79058(17) 0.0416(6) Uani 1 1 d . . .
H5A H -0.0056 1.0054 0.7519 0.050 Uiso 1 1 calc R . .
C8 C 0.4343(3) 0.38527(19) 0.71619(17) 0.0508(7) Uani 1 1 d . . .
H8A H 0.4837 0.3726 0.6657 0.061 Uiso 1 1 calc R . .
C10 C 0.2352(3) 0.35631(17) 0.81465(18) 0.0402(6) Uani 1 1 d . . .
H10A H 0.1495 0.3243 0.8309 0.048 Uiso 1 1 calc R . .
C3 C 0.2537(3) 1.11472(17) 0.8483(2) 0.0462(7) Uani 1 1 d . . .
H3B H 0.3014 1.1696 0.8487 0.055 Uiso 1 1 calc R . .
C9 C 0.3053(3) 0.33837(18) 0.73889(18) 0.0446(7) Uani 1 1 d . . .
H9A H 0.2661 0.2951 0.7033 0.053 Uiso 1 1 calc R . .
C7 C 0.4901(3) 0.45065(18) 0.76795(17) 0.0434(6) Uani 1 1 d . . .
H7A H 0.5768 0.4819 0.7517 0.052 Uiso 1 1 calc R . .
C2 C 0.2989(3) 1.05133(17) 0.90604(17) 0.0408(6) Uani 1 1 d . . .
H2B H 0.3740 1.0642 0.9457 0.049 Uiso 1 1 calc R . .
C19 C 0.2618(3) 0.6096(2) 0.61415(18) 0.0501(7) Uani 1 1 d . . .
H19A H 0.2287 0.5769 0.6626 0.075 Uiso 1 1 calc R . .
H19B H 0.3324 0.5746 0.5821 0.075 Uiso 1 1 calc R . .
H19C H 0.1750 0.6240 0.5798 0.075 Uiso 1 1 calc R . .
C20 C 0.3865(3) 0.7423(3) 0.56968(18) 0.0621(9) Uani 1 1 d . . .
H20A H 0.4353 0.7953 0.5892 0.093 Uiso 1 1 calc R . .
H20B H 0.2998 0.7575 0.5356 0.093 Uiso 1 1 calc R . .
H20C H 0.4575 0.7084 0.5368 0.093 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 0.0574(4) 0.0309(3) 0.0393(3) -0.0052(3) -0.0148(3) -0.0084(3)
O1 0.0275(7) 0.0349(9) 0.0346(8) -0.0014(7) 0.0016(7) -0.0071(7)
O2 0.0347(7) 0.0303(9) 0.0332(8) 0.0012(7) 0.0062(7) 0.0048(7)
N2 0.0324(9) 0.0276(10) 0.0249(9) -0.0034(8) -0.0061(7) -0.0019(8)
C14 0.0257(10) 0.0273(12) 0.0251(10) 0.0001(9) 0.0002(9) -0.0011(9)
N3 0.0276(8) 0.0246(10) 0.0246(9) -0.0023(8) 0.0013(7) -0.0048(8)
N1 0.0277(8) 0.0222(9) 0.0319(10) 0.0003(8) -0.0042(8) -0.0034(8)
N4 0.0280(8) 0.0318(10) 0.0244(9) -0.0031(8) 0.0021(8) 0.0025(8)
C1 0.0267(10) 0.0277(12) 0.0291(11) 0.0009(10) 0.0047(8) 0.0035(10)
C16 0.0282(10) 0.0237(11) 0.0213(10) 0.0057(9) -0.0034(8) 0.0034(9)
C13 0.0335(11) 0.0280(12) 0.0343(12) -0.0013(10) -0.0033(10) 0.0051(10)
C15 0.0252(10) 0.0320(13) 0.0229(10) -0.0030(10) 0.0032(9) 0.0015(10)
C6 0.0357(11) 0.0306(13) 0.0339(12) -0.0019(11) -0.0028(10) 0.0019(10)
C12 0.0325(10) 0.0223(11) 0.0332(11) 0.0003(10) 0.0013(9) 0.0042(10)
C11 0.0393(12) 0.0293(13) 0.0347(13) 0.0007(11) 0.0083(10) 0.0054(11)
C4 0.0476(14) 0.0370(14) 0.0431(14) 0.0095(13) 0.0006(12) 0.0125(12)
C17 0.0300(11) 0.0244(12) 0.0287(11) -0.0023(10) -0.0021(9) -0.0025(10)
N5 0.0363(10) 0.0529(13) 0.0278(10) -0.0019(10) 0.0018(8) -0.0010(10)
C18 0.0380(12) 0.0395(14) 0.0314(12) 0.0012(11) -0.0033(10) 0.0065(11)
C5 0.0437(13) 0.0442(15) 0.0369(13) 0.0035(12) -0.0057(11) 0.0054(12)
C8 0.0706(17) 0.0408(15) 0.0410(14) -0.0130(13) 0.0206(14) -0.0076(15)
C10 0.0396(12) 0.0261(12) 0.0549(16) 0.0017(12) 0.0079(12) -0.0054(11)
C3 0.0513(15) 0.0282(14) 0.0592(17) 0.0073(13) -0.0028(14) -0.0023(12)
C9 0.0554(15) 0.0316(14) 0.0467(15) -0.0087(12) -0.0021(13) -0.0071(12)
C7 0.0472(13) 0.0340(14) 0.0489(15) -0.0057(12) 0.0159(12) -0.0094(12)
C2 0.0414(13) 0.0308(13) 0.0500(15) 0.0037(12) -0.0078(11) -0.0025(11)
C19 0.0453(15) 0.069(2) 0.0360(14) -0.0151(14) 0.0003(11) -0.0010(15)
C20 0.0587(17) 0.087(2) 0.0403(15) 0.0108(17) 0.0121(14) -0.0007(18)

_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 C15 1.669(2) . ?
O1 C16 1.227(3) . ?
O2 C17 1.238(3) . ?
N2 C15 1.364(3) . ?
N2 N3 1.387(3) . ?
C14 N4 1.449(3) . ?
C14 C16 1.525(3) . ?
C14 C13 1.533(3) . ?
N3 C16 1.348(3) . ?
N1 C15 1.345(3) . ?
N1 C1 1.424(3) . ?
N4 C17 1.334(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.391(3) . ?
C13 C12 1.506(3) . ?
C6 C5 1.371(4) . ?
C12 C7 1.374(3) . ?
C12 C11 1.394(3) . ?
C11 C10 1.386(4) . ?
C4 C3 1.359(4) . ?
C4 C5 1.384(4) . ?
C17 C18 1.504(3) . ?
N5 C20 1.447(4) . ?
N5 C19 1.454(4) . ?
N5 C18 1.462(3) . ?
C8 C7 1.376(4) . ?
C8 C9 1.382(4) . ?
C10 C9 1.377(4) . ?
C3 C2 1.384(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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N2 N3 121.95(17) . . ?
N4 C14 C16 107.53(18) . . ?
N4 C14 C13 110.51(18) . . ?
C16 C14 C13 110.42(17) . . ?
C16 N3 N2 119.77(18) . . ?
C15 N1 C1 130.81(19) . . ?
C17 N4 C14 121.95(18) . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 N1 125.3(2) . . ?
C6 C1 N1 115.8(2) . . ?
O1 C16 N3 122.2(2) . . ?
O1 C16 C14 121.51(19) . . ?
N3 C16 C14 116.28(18) . . ?
C12 C13 C14 111.79(17) . . ?
N1 C15 N2 115.10(19) . . ?
N1 C15 S1 127.67(18) . . ?
N2 C15 S1 117.20(16) . . ?
C5 C6 C1 120.4(2) . . ?
C7 C12 C11 118.2(2) . . ?
C7 C12 C13 121.1(2) . . ?
C11 C12 C13 120.6(2) . . ?
C10 C11 C12 120.7(2) . . ?
C3 C4 C5 118.7(2) . . ?
O2 C17 N4 122.7(2) . . ?
O2 C17 C18 120.7(2) . . ?
N4 C17 C18 116.50(19) . . ?
C20 N5 C19 111.1(2) . . ?
C20 N5 C18 111.3(2) . . ?
C19 N5 C18 111.2(2) . . ?
N5 C18 C17 113.9(2) . . ?
C6 C5 C4 120.8(2) . . ?
C7 C8 C9 120.3(2) . . ?
C9 C10 C11 120.1(2) . . ?
C4 C3 C2 121.9(2) . . ?
C10 C9 C8 119.4(2) . . ?
C12 C7 C8 121.4(2) . . ?
C3 C2 C1 119.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.035



_database_code_depnum_ccdc_archive 'CCDC 914552'