# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_GYY4137-3
_database_code_depnum_ccdc_archive 'CCDC 1053548'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N O2 P S2, C4 H10 N O'
_chemical_formula_sum            'C15 H25 N2 O3 P S2'
_chemical_formula_weight         376.46

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'
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'
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   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   24.2051(3)
_cell_length_b                   8.9799(2)
_cell_length_c                   17.2946(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.4120(10)
_cell_angle_gamma                90.00
_cell_volume                     3684.82(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    26732
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    0.391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9260
_exptl_absorpt_correction_T_max  0.9694
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26236
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4230
_reflns_number_gt                3784
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0251P)²+4.9390P] where P=(Fo²+2Fc²)/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_number_reflns         4230
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_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
C1 C 0.92005(9) -0.51445(19) 0.28273(11) 0.0384(4) Uani 1 1 d . . .
H1A H 0.8833 -0.5434 0.2515 0.058 Uiso 1 1 calc R . .
H1B H 0.9284 -0.5749 0.3308 0.058 Uiso 1 1 calc R . .
H1C H 0.9493 -0.5305 0.2517 0.058 Uiso 1 1 calc R . .
C2 C 0.90844(6) -0.25903(17) 0.24406(9) 0.0243(3) Uani 1 1 d . . .
C3 C 0.90623(7) -0.11158(18) 0.26853(9) 0.0290(3) Uani 1 1 d . . .
H3 H 0.9114 -0.0888 0.3231 0.035 Uiso 1 1 calc R . .
C4 C 0.89654(7) 0.00118(18) 0.21341(9) 0.0283(3) Uani 1 1 d . . .
H4 H 0.8951 0.1015 0.2304 0.034 Uiso 1 1 calc R . .
C5 C 0.88882(6) -0.03048(17) 0.13283(9) 0.0228(3) Uani 1 1 d . . .
C6 C 0.89019(6) -0.17809(17) 0.10922(9) 0.0233(3) Uani 1 1 d . . .
H6 H 0.8845 -0.2009 0.0546 0.028 Uiso 1 1 calc R . .
C7 C 0.89979(6) -0.29326(17) 0.16414(9) 0.0243(3) Uani 1 1 d . . .
H7 H 0.9004 -0.3938 0.1473 0.029 Uiso 1 1 calc R . .
C8 C 0.98851(6) 0.16569(17) 0.11259(9) 0.0231(3) Uani 1 1 d . . .
H8A H 0.9887 0.0762 0.1461 0.028 Uiso 1 1 calc R . .
H8B H 0.9841 0.2546 0.1447 0.028 Uiso 1 1 calc R . .
C9 C 1.04350(6) 0.17548(17) 0.08314(9) 0.0241(3) Uani 1 1 d . . .
H9A H 1.0754 0.1795 0.1288 0.029 Uiso 1 1 calc R . .
H9B H 1.0480 0.0851 0.0522 0.029 Uiso 1 1 calc R . .
C10 C 0.94287(6) 0.28782(17) -0.00707(9) 0.0241(3) Uani 1 1 d . . .
H10A H 0.9366 0.3796 0.0218 0.029 Uiso 1 1 calc R . .
H10B H 0.9123 0.2800 -0.0543 0.029 Uiso 1 1 calc R . .
C11 C 0.99933(6) 0.29652(18) -0.03199(9) 0.0263(3) Uani 1 1 d . . .
H11A H 1.0043 0.2076 -0.0638 0.032 Uiso 1 1 calc R . .
H11B H 1.0002 0.3857 -0.0654 0.032 Uiso 1 1 calc R . .
C12 C 0.70025(8) -0.0448(2) 0.05424(10) 0.0343(4) Uani 1 1 d . . .
H12A H 0.7089 -0.0675 0.0019 0.041 Uiso 1 1 calc R . .
H12B H 0.6589 -0.0490 0.0497 0.041 Uiso 1 1 calc R . .
C13 C 0.72820(8) -0.1580(2) 0.11375(12) 0.0396(4) Uani 1 1 d . . .
H13A H 0.7135 -0.2584 0.0974 0.047 Uiso 1 1 calc R . .
H13B H 0.7693 -0.1580 0.1154 0.047 Uiso 1 1 calc R . .
C14 C 0.71497(8) 0.1390(2) 0.16196(10) 0.0348(4) Uani 1 1 d . . .
H14A H 0.6745 0.1479 0.1640 0.042 Uiso 1 1 calc R . .
H14B H 0.7336 0.2347 0.1796 0.042 Uiso 1 1 calc R . .
C15 C 0.74134(8) 0.0152(2) 0.21602(11) 0.0412(4) Uani 1 1 d . . .
H15A H 0.7825 0.0134 0.2178 0.049 Uiso 1 1 calc R . .
H15B H 0.7353 0.0349 0.2701 0.049 Uiso 1 1 calc R . .
N1 N 0.72115(6) 0.10672(16) 0.07967(8) 0.0280(3) Uani 1 1 d . . .
O3 O 0.71797(6) -0.12572(14) 0.19032(8) 0.0395(3) Uani 1 1 d . . .
N3 N 0.94146(5) 0.15710(14) 0.04406(7) 0.0208(2) Uani 1 1 d . . .
O1 O 0.91882(5) -0.36116(12) 0.30341(6) 0.0293(3) Uani 1 1 d . . .
O2 O 1.04474(4) 0.30435(12) 0.03500(6) 0.0245(2) Uani 1 1 d . . .
P1 P 0.876054(16) 0.11871(4) 0.06085(2) 0.02125(10) Uani 1 1 d . . .
S1 S 0.828170(16) 0.04771(4) -0.03927(2) 0.02585(10) Uani 1 1 d . . .
S2 S 0.843178(16) 0.29309(4) 0.10769(2) 0.02669(10) Uani 1 1 d . . .
H4N H 0.7570(10) 0.119(2) 0.0757(12) 0.047(6) Uiso 1 1 d . . .
H3N H 0.7027(9) 0.172(3) 0.0473(13) 0.044(6) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 O1 1.424(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.3623(18) . ?
C2 C7 1.391(2) . ?
C2 C3 1.394(2) . ?
C3 C4 1.379(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 P1 1.8132(15) . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N3 1.4744(18) . ?
C8 C9 1.519(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O2 1.4294(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N3 1.4741(18) . ?
C10 C11 1.514(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O2 1.4323(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N1 1.487(2) . ?
C12 C13 1.508(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O3 1.424(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N1 1.489(2) . ?
C14 C15 1.510(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O3 1.421(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
N1 H4N 0.89(2) . ?
N1 H3N 0.87(2) . ?
N3 P1 1.7003(12) . ?
P1 S1 1.9884(5) . ?
P1 S2 1.9992(5) . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 124.69(14) . . ?
O1 C2 C3 115.03(13) . . ?
C7 C2 C3 120.28(14) . . ?
C4 C3 C2 119.94(15) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.71(15) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.73(14) . . ?
C6 C5 P1 120.92(11) . . ?
C4 C5 P1 120.34(12) . . ?
C5 C6 C7 121.24(14) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 119.07(14) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
N3 C8 C9 108.80(12) . . ?
N3 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N3 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
O2 C9 C8 111.28(12) . . ?
O2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
O2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N3 C10 C11 109.95(12) . . ?
N3 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N3 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O2 C11 C10 111.33(12) . . ?
O2 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
O2 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C12 C13 109.54(15) . . ?
N1 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
N1 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
O3 C13 C12 111.13(15) . . ?
O3 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
O3 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
N1 C14 C15 109.80(15) . . ?
N1 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
N1 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O3 C15 C14 111.61(15) . . ?
O3 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
O3 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C12 N1 C14 111.59(13) . . ?
C12 N1 H4N 111.5(14) . . ?
C14 N1 H4N 109.5(14) . . ?
C12 N1 H3N 109.1(14) . . ?
C14 N1 H3N 110.2(14) . . ?
H4N N1 H3N 104.6(19) . . ?
C15 O3 C13 109.89(14) . . ?
C10 N3 C8 109.55(11) . . ?
C10 N3 P1 113.37(9) . . ?
C8 N3 P1 118.07(10) . . ?
C2 O1 C1 118.13(13) . . ?
C9 O2 C11 109.28(11) . . ?
N3 P1 C5 103.25(6) . . ?
N3 P1 S1 108.56(5) . . ?
C5 P1 S1 110.59(5) . . ?
N3 P1 S2 111.66(5) . . ?
C5 P1 S2 109.14(5) . . ?
S1 P1 S2 113.19(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.051

