# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_214LR
_database_code_depnum_ccdc_archive 'CCDC 817642'
_audit_update_record             
;
2011-03-16 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;
#TrackingRef '214LR.Cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N2 O3 P'
_chemical_formula_sum            'C17 H15 N2 O3 P'
_chemical_formula_weight         326.28

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.2009(8)
_cell_length_b                   8.7089(8)
_cell_length_c                   11.2790(11)
_cell_angle_alpha                78.414(2)
_cell_angle_beta                 83.899(3)
_cell_angle_gamma                73.626(2)
_cell_volume                     756.08(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2365
_cell_measurement_theta_min      3
_cell_measurement_theta_max      28

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(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 area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8362
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         28.99
_reflns_number_total             3992
_reflns_number_gt                3052
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'

_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 > 2sigma(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)+(0.0725P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3992
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
P1 P 0.25560(4) 0.91445(4) 0.36132(3) 0.01747(11) Uani 1 1 d . . .
O1 O 0.15801(12) 0.81532(12) 0.44682(9) 0.0216(2) Uani 1 1 d . . .
O3 O 0.14738(15) 1.38238(13) 0.18947(11) 0.0303(3) Uani 1 1 d . . .
O4 O -0.27863(14) 1.35725(14) 0.26765(10) 0.0292(3) Uani 1 1 d . . .
N1 N 0.21170(15) 1.11200(14) 0.36316(11) 0.0204(3) Uani 1 1 d . . .
H1N H 0.2545 1.1469 0.4258 0.059(7) Uiso 1 1 d R . .
N2 N 0.04545(15) 1.20349(15) 0.33420(11) 0.0219(3) Uani 1 1 d . . .
H2N H -0.0372 1.1955 0.3923 0.026 Uiso 1 1 d R . .
C1 C 0.02863(19) 1.33603(17) 0.24449(13) 0.0223(3) Uani 1 1 d . . .
C2 C -0.14824(19) 1.42002(18) 0.21186(14) 0.0240(3) Uani 1 1 d . . .
C3 C -0.2081(2) 1.5508(2) 0.12620(16) 0.0306(4) Uani 1 1 d . . .
H3A H -0.1432 1.6149 0.0748 0.037 Uiso 1 1 calc R . .
C4 C -0.3859(2) 1.5743(2) 0.12746(16) 0.0361(4) Uani 1 1 d . . .
H4A H -0.4638 1.6576 0.0776 0.043 Uiso 1 1 calc R . .
C5 C -0.4234(2) 1.4554(2) 0.21328(16) 0.0340(4) Uani 1 1 d . . .
H5A H -0.5344 1.4413 0.2334 0.041 Uiso 1 1 calc R . .
C6 C 0.23149(17) 0.90464(17) 0.20674(13) 0.0178(3) Uani 1 1 d . . .
C7 C 0.27264(19) 1.01837(18) 0.11015(13) 0.0214(3) Uani 1 1 d . . .
H7A H 0.3073 1.1076 0.1255 0.026 Uiso 1 1 calc R . .
C8 C 0.2626(2) 1.00027(19) -0.00810(14) 0.0251(3) Uani 1 1 d . . .
H8A H 0.2897 1.0778 -0.0738 0.030 Uiso 1 1 calc R . .
C9 C 0.2132(2) 0.86947(19) -0.03088(14) 0.0261(3) Uani 1 1 d . . .
H9A H 0.2065 0.8579 -0.1121 0.031 Uiso 1 1 calc R . .
C10 C 0.17380(19) 0.75598(19) 0.06412(14) 0.0253(3) Uani 1 1 d . . .
H10A H 0.1404 0.6664 0.0482 0.030 Uiso 1 1 calc R . .
C11 C 0.18304(18) 0.77295(17) 0.18289(13) 0.0211(3) Uani 1 1 d . . .
H11A H 0.1563 0.6947 0.2481 0.025 Uiso 1 1 calc R . .
C12 C 0.47855(17) 0.84667(17) 0.38691(12) 0.0179(3) Uani 1 1 d . . .
C13 C 0.59571(19) 0.93110(18) 0.32904(13) 0.0223(3) Uani 1 1 d . . .
H13A H 0.5569 1.0362 0.2814 0.027 Uiso 1 1 calc R . .
C14 C 0.76883(19) 0.8607(2) 0.34149(14) 0.0252(3) Uani 1 1 d . . .
H14A H 0.8483 0.9186 0.3034 0.030 Uiso 1 1 calc R . .
C15 C 0.82622(18) 0.70585(19) 0.40937(14) 0.0237(3) Uani 1 1 d . . .
H15A H 0.9449 0.6568 0.4151 0.028 Uiso 1 1 calc R . .
C16 C 0.71152(19) 0.62296(18) 0.46848(15) 0.0250(3) Uani 1 1 d . . .
H16A H 0.7509 0.5178 0.5159 0.030 Uiso 1 1 calc R . .
C17 C 0.53722(19) 0.69463(18) 0.45805(14) 0.0227(3) Uani 1 1 d . . .
H17A H 0.4581 0.6388 0.5001 0.027 Uiso 1 1 calc R . .


_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
P1 O1 1.4855(10) . ?
P1 N1 1.6594(12) . ?
P1 C12 1.7916(14) . ?
P1 C6 1.7969(14) . ?
O3 C1 1.2202(18) . ?
O4 C2 1.3735(18) . ?
O4 C5 1.374(2) . ?
N1 N2 1.4065(16) . ?
N1 H1N 0.9552 . ?
N2 C1 1.3587(19) . ?
N2 H2N 0.8980 . ?
C1 C2 1.477(2) . ?
C2 C3 1.347(2) . ?
C3 C4 1.413(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.348(3) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
C6 C11 1.396(2) . ?
C6 C7 1.399(2) . ?
C7 C8 1.388(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.388(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.382(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C17 1.387(2) . ?
C12 C13 1.4008(19) . ?
C13 C14 1.389(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.381(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.396(2) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?

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 P1 N1 118.78(6) . . ?
O1 P1 C12 111.80(6) . . ?
N1 P1 C12 102.25(6) . . ?
O1 P1 C6 111.27(6) . . ?
N1 P1 C6 104.28(6) . . ?
C12 P1 C6 107.51(6) . . ?
C2 O4 C5 105.60(13) . . ?
N2 N1 P1 115.72(9) . . ?
N2 N1 H1N 113.1 . . ?
P1 N1 H1N 119.0 . . ?
C1 N2 N1 117.33(12) . . ?
C1 N2 H2N 121.5 . . ?
N1 N2 H2N 116.7 . . ?
O3 C1 N2 124.51(14) . . ?
O3 C1 C2 120.57(14) . . ?
N2 C1 C2 114.86(13) . . ?
C3 C2 O4 110.46(14) . . ?
C3 C2 C1 129.86(15) . . ?
O4 C2 C1 119.54(13) . . ?
C2 C3 C4 106.80(15) . . ?
C2 C3 H3A 126.6 . . ?
C4 C3 H3A 126.6 . . ?
C5 C4 C3 106.61(15) . . ?
C5 C4 H4A 126.7 . . ?
C3 C4 H4A 126.7 . . ?
C4 C5 O4 110.54(15) . . ?
C4 C5 H5A 124.7 . . ?
O4 C5 H5A 124.7 . . ?
C11 C6 C7 119.54(13) . . ?
C11 C6 P1 118.69(11) . . ?
C7 C6 P1 121.58(11) . . ?
C8 C7 C6 119.70(14) . . ?
C8 C7 H7A 120.2 . . ?
C6 C7 H7A 120.2 . . ?
C9 C8 C7 120.33(14) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C10 C9 C8 120.25(14) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 119.95(14) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C10 C11 C6 120.23(14) . . ?
C10 C11 H11A 119.9 . . ?
C6 C11 H11A 119.9 . . ?
C17 C12 C13 119.37(13) . . ?
C17 C12 P1 117.02(11) . . ?
C13 C12 P1 123.25(11) . . ?
C14 C13 C12 119.79(13) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C15 C14 C13 120.26(14) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C16 C15 C14 120.31(14) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C17 119.59(14) . . ?
C15 C16 H16A 120.2 . . ?
C17 C16 H16A 120.2 . . ?
C12 C17 C16 120.61(14) . . ?
C12 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?

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
O1 P1 N1 N2 -61.95(12) . . . . ?
C12 P1 N1 N2 174.48(9) . . . . ?
C6 P1 N1 N2 62.58(11) . . . . ?
P1 N1 N2 C1 -126.56(12) . . . . ?
N1 N2 C1 O3 -1.5(2) . . . . ?
N1 N2 C1 C2 175.62(12) . . . . ?
C5 O4 C2 C3 -0.27(18) . . . . ?
C5 O4 C2 C1 -176.37(13) . . . . ?
O3 C1 C2 C3 -1.0(3) . . . . ?
N2 C1 C2 C3 -178.26(16) . . . . ?
O3 C1 C2 O4 174.25(13) . . . . ?
N2 C1 C2 O4 -3.0(2) . . . . ?
O4 C2 C3 C4 0.47(19) . . . . ?
C1 C2 C3 C4 176.05(15) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 O4 0.3(2) . . . . ?
C2 O4 C5 C4 -0.05(18) . . . . ?
O1 P1 C6 C11 -22.00(13) . . . . ?
N1 P1 C6 C11 -151.21(11) . . . . ?
C12 P1 C6 C11 100.74(12) . . . . ?
O1 P1 C6 C7 163.00(11) . . . . ?
N1 P1 C6 C7 33.79(13) . . . . ?
C12 P1 C6 C7 -74.26(13) . . . . ?
C11 C6 C7 C8 0.9(2) . . . . ?
P1 C6 C7 C8 175.83(11) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C6 0.2(2) . . . . ?
C7 C6 C11 C10 -0.8(2) . . . . ?
P1 C6 C11 C10 -175.86(11) . . . . ?
O1 P1 C12 C17 14.98(14) . . . . ?
N1 P1 C12 C17 143.11(11) . . . . ?
C6 P1 C12 C17 -107.43(12) . . . . ?
O1 P1 C12 C13 -171.89(11) . . . . ?
N1 P1 C12 C13 -43.76(13) . . . . ?
C6 P1 C12 C13 65.71(13) . . . . ?
C17 C12 C13 C14 1.3(2) . . . . ?
P1 C12 C13 C14 -171.72(11) . . . . ?
C12 C13 C14 C15 1.1(2) . . . . ?
C13 C14 C15 C16 -2.3(2) . . . . ?
C14 C15 C16 C17 1.0(2) . . . . ?
C13 C12 C17 C16 -2.5(2) . . . . ?
P1 C12 C17 C16 170.93(11) . . . . ?
C15 C16 C17 C12 1.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2N O1 2_576 0.90 1.97 2.8332(16) 160 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_s201
_database_code_depnum_ccdc_archive 'CCDC 985968'
_audit_update_record             
;
2014-02-10 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H14 N3 O3 P S'
_chemical_formula_sum            'C5 H14 N3 O3 P S'
_chemical_formula_weight         227.22

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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'
'-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                   9.0600(5)
_cell_length_b                   9.2136(5)
_cell_length_c                   25.3700(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2117.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1631
_cell_measurement_theta_min      3
_cell_measurement_theta_max      28

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_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 DUO CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23476
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         28.99
_reflns_number_total             2822
_reflns_number_gt                2623
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.0429P)²+4.1055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2822
_refine_ls_number_parameters     135
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
P1 P 0.04543(5) 0.89779(5) 0.382549(18) 0.01055(12) Uani 1 1 d D . .
S1 S 0.04075(5) 0.68785(5) 0.384758(18) 0.01349(12) Uani 1 1 d . A .
O1 O 0.12913(16) 1.30908(15) 0.27515(6) 0.0161(3) Uani 1 1 d . . .
N1 N 0.12296(17) 0.95311(17) 0.32701(6) 0.0115(3) Uani 1 1 d . A .
H1N H 0.1977 0.9009 0.3134 0.030(8) Uiso 1 1 d R . .
N2 N 0.14481(18) 1.10387(17) 0.32307(6) 0.0133(3) Uani 1 1 d . . .
H2N H 0.2220 1.1443 0.3399 0.013(6) Uiso 1 1 d R A .
N3 N 0.0021(2) 1.10882(18) 0.24760(7) 0.0176(3) Uani 1 1 d . . .
H3NB H -0.0166 1.0131 0.2501 0.030(7) Uiso 1 1 d R A .
H3NA H -0.0232 1.1568 0.2181 0.029(7) Uiso 1 1 d R . .
O2 O -0.10760(15) 0.97772(15) 0.38612(5) 0.0141(3) Uani 1 1 d . A .
O3 O 0.1330(6) 0.9787(5) 0.42723(19) 0.0162(12) Uani 0.697(3) 1 d PD A 2
O3' O 0.1150(18) 0.9684(14) 0.4332(6) 0.0162(12) Uani 0.303(3) 1 d PD A 1
C1 C 0.0933(2) 1.1793(2) 0.28048(7) 0.0120(3) Uani 1 1 d . A .
C2 C -0.2283(2) 0.9388(2) 0.35030(8) 0.0171(4) Uani 1 1 d . . .
H2A H -0.1901 0.8772 0.3214 0.020 Uiso 1 1 calc R A .
H2B H -0.2711 1.0277 0.3346 0.020 Uiso 1 1 calc R . .
C3 C -0.3454(2) 0.8577(3) 0.38049(10) 0.0266(5) Uani 1 1 d . A .
H3A H -0.4261 0.8316 0.3566 0.040 Uiso 1 1 calc R . .
H3B H -0.3834 0.9194 0.4089 0.040 Uiso 1 1 calc R . .
H3C H -0.3026 0.7693 0.3956 0.040 Uiso 1 1 calc R . .
C4' C 0.2568(8) 0.9123(8) 0.4530(2) 0.0217(6) Uani 0.303(3) 1 d PD A 1
H4'A H 0.3253 0.9935 0.4603 0.026 Uiso 0.303(3) 1 calc PR A 1
H4'B H 0.3027 0.8478 0.4264 0.026 Uiso 0.303(3) 1 calc PR A 1
C4 C 0.1631(3) 0.9163(4) 0.47959(11) 0.0217(6) Uani 0.697(3) 1 d PD A 2
H4A H 0.0954 0.8339 0.4863 0.026 Uiso 0.697(3) 1 calc PR A 2
H4B H 0.1463 0.9905 0.5072 0.026 Uiso 0.697(3) 1 calc PR A 2
C5' C 0.2262(10) 0.8300(10) 0.5024(3) 0.0333(8) Uani 0.303(3) 1 d PD A 1
H5'A H 0.3186 0.7897 0.5161 0.050 Uiso 0.303(3) 1 calc PR A 1
H5'B H 0.1571 0.7509 0.4948 0.050 Uiso 0.303(3) 1 calc PR A 1
H5'C H 0.1829 0.8954 0.5286 0.050 Uiso 0.303(3) 1 calc PR A 1
C5 C 0.3191(4) 0.8651(4) 0.48161(15) 0.0333(8) Uani 0.697(3) 1 d PD A 2
H5A H 0.3397 0.8244 0.5165 0.050 Uiso 0.697(3) 1 calc PR A 2
H5B H 0.3855 0.9470 0.4749 0.050 Uiso 0.697(3) 1 calc PR A 2
H5C H 0.3345 0.7903 0.4547 0.050 Uiso 0.697(3) 1 calc PR A 2


_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
P1 O3' 1.572(3) . ?
P1 O3 1.5718(19) . ?
P1 O2 1.5725(14) . ?
P1 N1 1.6548(16) . ?
P1 S1 1.9356(7) . ?
O1 C1 1.247(2) . ?
N1 N2 1.407(2) . ?
N1 H1N 0.9000 . ?
N2 C1 1.367(2) . ?
N2 H2N 0.9000 . ?
N3 C1 1.341(3) . ?
N3 H3NB 0.9001 . ?
N3 H3NA 0.9001 . ?
O2 C2 1.466(2) . ?
O3 C4 1.473(6) . ?
O3' C4' 1.473(6) . ?
C2 C3 1.507(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4' C5' 1.490(5) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C4 C5 1.491(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5' H5'A 0.9800 . ?
C5' H5'B 0.9800 . ?
C5' H5'C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

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
O3' P1 O2 96.5(4) . . ?
O3 P1 O2 100.45(18) . . ?
O3' P1 N1 113.4(9) . . ?
O3 P1 N1 104.7(3) . . ?
O2 P1 N1 106.20(8) . . ?
O3' P1 S1 113.5(5) . . ?
O3 P1 S1 117.66(19) . . ?
O2 P1 S1 116.56(6) . . ?
N1 P1 S1 109.98(6) . . ?
N2 N1 P1 115.12(12) . . ?
N2 N1 H1N 113.2 . . ?
P1 N1 H1N 118.9 . . ?
C1 N2 N1 120.67(15) . . ?
C1 N2 H2N 115.4 . . ?
N1 N2 H2N 119.0 . . ?
C1 N3 H3NB 123.1 . . ?
C1 N3 H3NA 115.9 . . ?
H3NB N3 H3NA 119.5 . . ?
C2 O2 P1 120.48(12) . . ?
C4 O3 P1 123.9(4) . . ?
C4' O3' P1 118.9(6) . . ?
O1 C1 N3 123.86(18) . . ?
O1 C1 N2 118.97(17) . . ?
N3 C1 N2 117.13(17) . . ?
O2 C2 C3 109.36(17) . . ?
O2 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
O2 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O3' C4' C5' 107.7(11) . . ?
O3' C4' H4'A 110.2 . . ?
C5' C4' H4'A 110.2 . . ?
O3' C4' H4'B 110.2 . . ?
C5' C4' H4'B 110.2 . . ?
H4'A C4' H4'B 108.5 . . ?
O3 C4 C5 109.3(4) . . ?
O3 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
O3 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
C4' C5' H5'A 109.5 . . ?
C4' C5' H5'B 109.5 . . ?
H5'A C5' H5'B 109.5 . . ?
C4' C5' H5'C 109.5 . . ?
H5'A C5' H5'C 109.5 . . ?
H5'B C5' H5'C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
O3' P1 N1 N2 -46.1(4) . . . . ?
O3 P1 N1 N2 -47.13(19) . . . . ?
O2 P1 N1 N2 58.62(14) . . . . ?
S1 P1 N1 N2 -174.43(11) . . . . ?
P1 N1 N2 C1 -126.95(16) . . . . ?
O3' P1 O2 C2 -172.8(8) . . . . ?
O3 P1 O2 C2 179.2(3) . . . . ?
N1 P1 O2 C2 70.44(15) . . . . ?
S1 P1 O2 C2 -52.46(15) . . . . ?
O3' P1 O3 C4 40(3) . . . . ?
O2 P1 O3 C4 103.7(4) . . . . ?
N1 P1 O3 C4 -146.3(4) . . . . ?
S1 P1 O3 C4 -23.9(5) . . . . ?
O3 P1 O3' C4' -72(3) . . . . ?
O2 P1 O3' C4' 170.9(14) . . . . ?
N1 P1 O3' C4' -78.2(15) . . . . ?
S1 P1 O3' C4' 48.2(18) . . . . ?
N1 N2 C1 O1 -171.73(17) . . . . ?
N1 N2 C1 N3 10.4(3) . . . . ?
P1 O2 C2 C3 107.87(17) . . . . ?
P1 O3' C4' C5' -107.8(15) . . . . ?
P1 O3 C4 C5 102.5(5) . . . . ?

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
_geom_hbond_publ_flag
N3 H3NB O1 0.90 2.23 3.062(2) 153 3_545 ?
N1 H1N O1 0.90 2.03 2.922(2) 171 8_655 ?
N3 H3NA S1 0.90 2.63 3.4579(19) 154 3_555 ?
N2 H2N S1 0.90 2.47 3.3413(17) 165 8_665 ?



_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.069





