# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H21 N4 O2 P S2'
_chemical_formula_sum            'C12 H21 N4 O2 P S2'
_chemical_formula_weight         348.42

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   17.145(3)
_cell_length_b                   14.7090(18)
_cell_length_c                   7.0193(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.319(15)
_cell_angle_gamma                90.00
_cell_volume                     1767.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2476
_cell_measurement_theta_min      2.7464
_cell_measurement_theta_max      21.2246

_exptl_crystal_description       block
_exptl_crystal_colour            yellow-brown
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.400
_exptl_absorpt_correction_T_min  0.57057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
Data cut-off 1A
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '122 images, ΔΦ 2.5°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1396
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         18.84
_reflns_number_total             1396
_reflns_number_gt                1244
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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 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)+(0.0541P)²+41.3103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1396
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.1307
_refine_ls_wR_factor_ref         0.3384
_refine_ls_wR_factor_gt          0.3356
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_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 0.3251(4) -0.0497(4) 0.6321(8) 0.0698(19) Uani 1 1 d . . .
P1 P 0.2851(3) 0.0144(3) 0.4043(7) 0.0458(16) Uani 1 1 d . . .
O1 O 0.2700(7) -0.0445(8) 0.2199(19) 0.061(4) Uani 1 1 d . . .
C2 C 0.2673(11) -0.1445(11) 0.206(3) 0.061(6) Uani 1 1 d . . .
H2 H 0.2586 -0.1686 0.3336 0.073 Uiso 1 1 calc R . .
C4 C 0.3464(13) -0.1755(13) 0.152(3) 0.077(7) Uani 1 1 d . . .
H4B H 0.3547 -0.1563 0.0242 0.116 Uiso 1 1 calc R . .
H4C H 0.3493 -0.2406 0.1595 0.116 Uiso 1 1 calc R . .
H4A H 0.3859 -0.1494 0.2381 0.116 Uiso 1 1 calc R . .
C3 C 0.2012(12) -0.1690(14) 0.081(3) 0.074(7) Uani 1 1 d . . .
H3A H 0.1550 -0.1408 0.1250 0.112 Uiso 1 1 calc R . .
H3B H 0.1949 -0.2339 0.0817 0.112 Uiso 1 1 calc R . .
H3C H 0.2096 -0.1488 -0.0457 0.112 Uiso 1 1 calc R . .
O2 O 0.3370(7) 0.0957(7) 0.342(2) 0.062(4) Uani 1 1 d . . .
C5 C 0.4210(11) 0.0840(13) 0.321(4) 0.073(7) Uani 1 1 d . . .
H5 H 0.4368 0.0238 0.3685 0.088 Uiso 1 1 calc R . .
C7 C 0.4359(15) 0.0895(19) 0.114(4) 0.118(10) Uani 1 1 d . . .
H7A H 0.4144 0.0369 0.0490 0.178 Uiso 1 1 calc R . .
H7B H 0.4912 0.0919 0.0987 0.178 Uiso 1 1 calc R . .
H7C H 0.4117 0.1433 0.0598 0.178 Uiso 1 1 calc R . .
C6 C 0.4616(14) 0.1532(18) 0.438(4) 0.118(10) Uani 1 1 d . . .
H6C H 0.5169 0.1425 0.4397 0.177 Uiso 1 1 calc R . .
H6A H 0.4444 0.1504 0.5652 0.177 Uiso 1 1 calc R . .
H6B H 0.4502 0.2122 0.3846 0.177 Uiso 1 1 calc R . .
N1 N 0.2052(8) 0.0778(9) 0.422(2) 0.051(4) Uani 1 1 d . . .
H1N H 0.2093 0.1339 0.3895 0.061 Uiso 1 1 calc R . .
C1 C 0.1341(12) 0.0517(13) 0.481(3) 0.060(6) Uani 1 1 d . . .
S2 S 0.1120(3) -0.0609(3) 0.5033(10) 0.070(2) Uani 1 1 d . . .
N2 N 0.0798(8) 0.1126(10) 0.504(2) 0.047(4) Uani 1 1 d . . .
H2N H 0.0345 0.0909 0.5241 0.057 Uiso 1 1 calc R . .
C11 C 0.0844(11) 0.2127(11) 0.500(2) 0.041(5) Uani 1 1 d . . .
C16 C 0.0209(11) 0.2619(15) 0.543(3) 0.069(7) Uani 1 1 d . . .
H16 H -0.0263 0.2343 0.5682 0.082 Uiso 1 1 calc R . .
C15 C 0.0301(13) 0.3552(13) 0.549(3) 0.069(7) Uani 1 1 d . . .
H15 H -0.0096 0.3930 0.5866 0.083 Uiso 1 1 calc R . .
C14 C 0.0983(14) 0.3892(14) 0.497(3) 0.061(6) Uani 1 1 d . . .
H14 H 0.1038 0.4520 0.4909 0.074 Uiso 1 1 calc R . .
C13 C 0.1589(13) 0.3371(14) 0.453(3) 0.056(6) Uani 1 1 d . . .
N12 N 0.1529(9) 0.2444(10) 0.456(2) 0.048(4) Uani 1 1 d . . .
N3 N 0.2304(11) 0.3681(11) 0.399(3) 0.080(6) Uani 1 1 d . . .
H3NA H 0.2390 0.4255 0.3919 0.096 Uiso 1 1 calc R . .
H3NB H 0.2663 0.3300 0.3733 0.096 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
S1 P1 1.947(7) . ?
P1 O1 1.567(13) . ?
P1 O2 1.569(12) . ?
P1 N1 1.667(14) . ?
O1 C2 1.47(2) . ?
C2 C3 1.44(3) . ?
C2 C4 1.50(3) . ?
C2 H2 0.9800 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 H4A 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
O2 C5 1.47(2) . ?
C5 C6 1.46(3) . ?
C5 C7 1.49(3) . ?
C5 H5 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 H6C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
N1 C1 1.37(2) . ?
N1 H1N 0.8600 . ?
C1 N2 1.31(2) . ?
C1 S2 1.709(19) . ?
N2 C11 1.48(2) . ?
N2 H2N 0.8600 . ?
C11 N12 1.32(2) . ?
C11 C16 1.36(2) . ?
C16 C15 1.38(3) . ?
C16 H16 0.9300 . ?
C15 C14 1.34(3) . ?
C15 H15 0.9300 . ?
C14 C13 1.34(3) . ?
C14 H14 0.9300 . ?
C13 N12 1.37(2) . ?
C13 N3 1.38(2) . ?
N3 H3NA 0.8600 . ?
N3 H3NB 0.8600 . ?

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 O2 105.1(7) . . ?
O1 P1 N1 105.9(7) . . ?
O2 P1 N1 94.3(7) . . ?
O1 P1 S1 116.4(5) . . ?
O2 P1 S1 114.8(6) . . ?
N1 P1 S1 117.6(6) . . ?
C2 O1 P1 127.4(13) . . ?
C3 C2 O1 108.1(16) . . ?
C3 C2 C4 117.4(19) . . ?
O1 C2 C4 107.1(14) . . ?
C3 C2 H2 108.0 . . ?
O1 C2 H2 108.0 . . ?
C4 C2 H2 108.0 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
H4B C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
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 . . ?
C5 O2 P1 121.1(11) . . ?
C6 C5 O2 107.5(17) . . ?
C6 C5 C7 114(2) . . ?
O2 C5 C7 108(2) . . ?
C6 C5 H5 108.9 . . ?
O2 C5 H5 108.9 . . ?
C7 C5 H5 108.9 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C6 H6C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
H6C C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6C C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 N1 P1 128.1(13) . . ?
C1 N1 H1N 116.0 . . ?
P1 N1 H1N 116.0 . . ?
N2 C1 N1 119.9(17) . . ?
N2 C1 S2 119.3(15) . . ?
N1 C1 S2 120.4(14) . . ?
C1 N2 C11 130.0(16) . . ?
C1 N2 H2N 115.0 . . ?
C11 N2 H2N 115.0 . . ?
N12 C11 C16 127.1(16) . . ?
N12 C11 N2 114.0(15) . . ?
C16 C11 N2 118.9(17) . . ?
C11 C16 C15 116.3(19) . . ?
C11 C16 H16 121.8 . . ?
C15 C16 H16 121.8 . . ?
C14 C15 C16 117.6(19) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
C15 C14 C13 123.3(19) . . ?
C15 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
C14 C13 N12 120.3(19) . . ?
C14 C13 N3 125.9(19) . . ?
N12 C13 N3 113.8(18) . . ?
C11 N12 C13 115.2(16) . . ?
C13 N3 H3NA 120.0 . . ?
C13 N3 H3NB 120.0 . . ?
H3NA N3 H3NB 120.0 . . ?

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
O2 P1 O1 C2 141.6(14) . . . . ?
N1 P1 O1 C2 -119.3(15) . . . . ?
S1 P1 O1 C2 13.4(17) . . . . ?
P1 O1 C2 C3 135.8(15) . . . . ?
P1 O1 C2 C4 -96.9(19) . . . . ?
O1 P1 O2 C5 -78.3(16) . . . . ?
N1 P1 O2 C5 173.9(16) . . . . ?
S1 P1 O2 C5 50.8(16) . . . . ?
P1 O2 C5 C6 -126.0(18) . . . . ?
P1 O2 C5 C7 110.3(19) . . . . ?
O1 P1 N1 C1 76.2(18) . . . . ?
O2 P1 N1 C1 -176.7(17) . . . . ?
S1 P1 N1 C1 -55.8(18) . . . . ?
P1 N1 C1 N2 173.3(14) . . . . ?
P1 N1 C1 S2 -13(3) . . . . ?
N1 C1 N2 C11 -9(3) . . . . ?
S2 C1 N2 C11 177.2(14) . . . . ?
C1 N2 C11 N12 4(3) . . . . ?
C1 N2 C11 C16 -175(2) . . . . ?
N12 C11 C16 C15 -3(3) . . . . ?
N2 C11 C16 C15 176.3(18) . . . . ?
C11 C16 C15 C14 5(3) . . . . ?
C16 C15 C14 C13 -4(3) . . . . ?
C15 C14 C13 N12 1(3) . . . . ?
C15 C14 C13 N3 -180(2) . . . . ?
C16 C11 N12 C13 -1(3) . . . . ?
N2 C11 N12 C13 -179.5(15) . . . . ?
C14 C13 N12 C11 1(3) . . . . ?
N3 C13 N12 C11 -177.8(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        18.84
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.133
_database_code_depnum_ccdc_archive 'CCDC 980848'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H25 N4 O3 P S2, C7 H6 O2'
_chemical_formula_sum            'C26 H31 N4 O5 P S2'
_chemical_formula_weight         574.64

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           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                   6.8774(5)
_cell_length_b                   14.6409(14)
_cell_length_c                   15.1569(12)
_cell_angle_alpha                70.775(8)
_cell_angle_beta                 89.447(6)
_cell_angle_gamma                83.841(7)
_cell_volume                     1432.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4828
_cell_measurement_theta_min      2.3653
_cell_measurement_theta_max      25.6671

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_min  0.90780
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '160 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12647
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.34
_reflns_number_total             4893
_reflns_number_gt                3840
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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 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)+(0.0726P)²+1.0595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4893
_refine_ls_number_parameters     337
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.49308(11) 0.84181(6) 0.73088(6) 0.0393(2) Uani 1 1 d . . .
P1 P 0.27564(11) 0.78090(5) 0.79753(5) 0.0283(2) Uani 1 1 d . . .
O2 O 0.0799(3) 0.80247(14) 0.73803(13) 0.0326(5) Uani 1 1 d . . .
C5 C 0.0525(5) 0.8635(2) 0.63990(19) 0.0359(7) Uani 1 1 d . . .
H5 H 0.1823 0.8699 0.6095 0.043 Uiso 1 1 calc R . .
C7 C -0.0401(5) 0.9622(2) 0.6377(2) 0.0460(8) Uani 1 1 d . . .
H7B H -0.1573 0.9547 0.6757 0.069 Uiso 1 1 calc R . .
H7C H -0.0767 1.0021 0.5731 0.069 Uiso 1 1 calc R . .
H7A H 0.0532 0.9939 0.6630 0.069 Uiso 1 1 calc R . .
C6 C -0.0721(5) 0.8119(3) 0.5942(2) 0.0463(8) Uani 1 1 d . . .
H6A H -0.0032 0.7484 0.5983 0.069 Uiso 1 1 calc R . .
H6B H -0.0975 0.8512 0.5284 0.069 Uiso 1 1 calc R . .
H6C H -0.1965 0.8026 0.6263 0.069 Uiso 1 1 calc R . .
O1 O 0.2167(3) 0.80545(14) 0.88904(13) 0.0334(5) Uani 1 1 d . . .
C2 C 0.1947(5) 0.9067(2) 0.8893(2) 0.0377(7) Uani 1 1 d . . .
H2 H 0.2214 0.9514 0.8256 0.045 Uiso 1 1 calc R . .
C3 C -0.0151(5) 0.9294(2) 0.9128(2) 0.0478(9) Uani 1 1 d . . .
H3A H -0.0425 0.8847 0.9746 0.072 Uiso 1 1 calc R . .
H3B H -0.1030 0.9219 0.8658 0.072 Uiso 1 1 calc R . .
H3C H -0.0358 0.9965 0.9134 0.072 Uiso 1 1 calc R . .
C4 C 0.3437(6) 0.9133(3) 0.9582(3) 0.0547(10) Uani 1 1 d . . .
H4A H 0.3311 0.9795 0.9611 0.082 Uiso 1 1 calc R . .
H4B H 0.4753 0.8973 0.9383 0.082 Uiso 1 1 calc R . .
H4C H 0.3218 0.8672 1.0201 0.082 Uiso 1 1 calc R . .
N1 N 0.3010(3) 0.65992(17) 0.85121(16) 0.0293(5) Uani 1 1 d . . .
H1N H 0.3003 0.6393 0.9127 0.035 Uiso 1 1 calc R . .
C1 C 0.3225(4) 0.5906(2) 0.8092(2) 0.0296(6) Uani 1 1 d . . .
S2 S 0.35037(13) 0.61364(6) 0.69425(5) 0.0393(2) Uani 1 1 d . . .
N2 N 0.3191(3) 0.49675(17) 0.86671(16) 0.0299(5) Uani 1 1 d . . .
H2N H 0.3501 0.4524 0.8399 0.036 Uiso 1 1 calc R . .
C11 C 0.2743(4) 0.4594(2) 0.96177(19) 0.0286(6) Uani 1 1 d . . .
C16 C 0.2529(4) 0.3599(2) 0.9991(2) 0.0311(6) Uani 1 1 d . . .
H16 H 0.2732 0.3184 0.9622 0.037 Uiso 1 1 calc R . .
C15 C 0.2013(4) 0.3244(2) 1.0913(2) 0.0339(7) Uani 1 1 d . . .
H15 H 0.1853 0.2574 1.1192 0.041 Uiso 1 1 calc R . .
C14 C 0.1727(4) 0.3866(2) 1.1434(2) 0.0322(6) Uani 1 1 d . . .
H14 H 0.1354 0.3630 1.2068 0.039 Uiso 1 1 calc R . .
C13 C 0.1997(4) 0.4837(2) 1.1014(2) 0.0287(6) Uani 1 1 d . . .
N12 N 0.2499(3) 0.52022(16) 1.01082(16) 0.0276(5) Uani 1 1 d . . .
N3 N 0.1708(4) 0.55571(18) 1.14528(16) 0.0312(5) Uani 1 1 d . . .
C8 C 0.1706(4) 0.5316(2) 1.2356(2) 0.0330(7) Uani 1 1 d . . .
H8 H 0.1953 0.4649 1.2727 0.040 Uiso 1 1 calc R . .
C21 C 0.1332(4) 0.6046(2) 1.2811(2) 0.0329(7) Uani 1 1 d . . .
C26 C 0.1318(5) 0.5753(3) 1.3794(2) 0.0394(7) Uani 1 1 d . . .
H26 H 0.1545 0.5081 1.4148 0.047 Uiso 1 1 calc R . .
C25 C 0.0981(5) 0.6429(3) 1.4252(2) 0.0448(8) Uani 1 1 d . . .
H25 H 0.0971 0.6222 1.4916 0.054 Uiso 1 1 calc R . .
C24 C 0.0657(5) 0.7411(3) 1.3735(2) 0.0440(8) Uani 1 1 d . . .
H24 H 0.0433 0.7876 1.4049 0.053 Uiso 1 1 calc R . .
C23 C 0.0655(5) 0.7723(2) 1.2770(2) 0.0407(8) Uani 1 1 d . . .
H23 H 0.0433 0.8398 1.2426 0.049 Uiso 1 1 calc R . .
C22 C 0.0978(4) 0.7048(2) 1.2298(2) 0.0360(7) Uani 1 1 d . . .
O3 O 0.0961(4) 0.73796(16) 1.13571(15) 0.0456(6) Uani 1 1 d . . .
H3 H 0.1102 0.6906 1.1157 0.068 Uiso 1 1 calc R . .
O4 O 0.5719(4) 0.84693(18) 0.18775(17) 0.0589(7) Uani 1 1 d . . .
H4 H 0.5859 0.7973 0.1711 0.088 Uiso 1 1 calc R . .
C31 C 0.5584(3) 0.81932(15) 0.28225(11) 0.0412(8) Uani 1 1 d G . .
C32 C 0.5279(4) 0.89257(11) 0.32200(14) 0.0495(9) Uani 1 1 d G . .
H32 H 0.5170 0.9589 0.2833 0.059 Uiso 1 1 calc R . .
C33 C 0.5132(4) 0.86877(14) 0.41831(15) 0.0481(9) Uani 1 1 d G . .
H33 H 0.4923 0.9188 0.4455 0.058 Uiso 1 1 calc R . .
C34 C 0.5290(3) 0.77172(17) 0.47486(11) 0.0463(8) Uani 1 1 d G . .
H34 H 0.5190 0.7555 0.5407 0.056 Uiso 1 1 calc R . .
C35 C 0.5596(3) 0.69847(12) 0.43510(13) 0.0465(8) Uani 1 1 d GU . .
H35 H 0.5704 0.6321 0.4738 0.056 Uiso 1 1 calc R . .
C36 C 0.5743(3) 0.72227(13) 0.33880(14) 0.0370(7) Uani 1 1 d GU . .
C37 C 0.6081(5) 0.6449(2) 0.2981(3) 0.0463(8) Uani 1 1 d U . .
H37 H 0.6189 0.5796 0.3394 0.056 Uiso 1 1 calc R . .
O5 O 0.6238(3) 0.65839(17) 0.21319(16) 0.0452(6) Uani 1 1 d U . .


_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 P1 1.9277(11) . ?
P1 O2 1.571(2) . ?
P1 O1 1.582(2) . ?
P1 N1 1.678(2) . ?
O2 C5 1.463(3) . ?
C5 C7 1.505(4) . ?
C5 C6 1.510(4) . ?
C5 H5 1.0000 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7A 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
O1 C2 1.476(3) . ?
C2 C4 1.502(5) . ?
C2 C3 1.512(5) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N1 C1 1.360(4) . ?
N1 H1N 0.8800 . ?
C1 N2 1.366(4) . ?
C1 S2 1.675(3) . ?
N2 C11 1.407(4) . ?
N2 H2N 0.8800 . ?
C11 N12 1.333(4) . ?
C11 C16 1.402(4) . ?
C16 C15 1.380(4) . ?
C16 H16 0.9500 . ?
C15 C14 1.387(4) . ?
C15 H15 0.9500 . ?
C14 C13 1.386(4) . ?
C14 H14 0.9500 . ?
C13 N12 1.355(4) . ?
C13 N3 1.417(4) . ?
N3 C8 1.297(4) . ?
C8 C21 1.451(4) . ?
C8 H8 0.9500 . ?
C21 C26 1.408(4) . ?
C21 C22 1.412(4) . ?
C26 C25 1.384(5) . ?
C26 H26 0.9500 . ?
C25 C24 1.388(5) . ?
C25 H25 0.9500 . ?
C24 C23 1.381(5) . ?
C24 H24 0.9500 . ?
C23 C22 1.398(4) . ?
C23 H23 0.9500 . ?
C22 O3 1.346(4) . ?
O3 H3 0.8400 . ?
O4 C31 1.359(3) . ?
O4 H4 0.8400 . ?
C31 C32 1.3900 . ?
C31 C36 1.3900 . ?
C32 C33 1.3900 . ?
C32 H32 0.9500 . ?
C33 C34 1.3900 . ?
C33 H33 0.9500 . ?
C34 C35 1.3900 . ?
C34 H34 0.9500 . ?
C35 C36 1.3900 . ?
C35 H35 0.9500 . ?
C36 C37 1.455(4) . ?
C37 O5 1.242(4) . ?
C37 H37 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
O2 P1 O1 104.79(11) . . ?
O2 P1 N1 104.67(12) . . ?
O1 P1 N1 94.50(11) . . ?
O2 P1 S1 114.75(9) . . ?
O1 P1 S1 116.40(9) . . ?
N1 P1 S1 119.03(10) . . ?
C5 O2 P1 125.74(18) . . ?
O2 C5 C7 107.5(2) . . ?
O2 C5 C6 106.5(2) . . ?
C7 C5 C6 113.9(3) . . ?
O2 C5 H5 109.6 . . ?
C7 C5 H5 109.6 . . ?
C6 C5 H5 109.6 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 O1 P1 121.09(18) . . ?
O1 C2 C4 107.4(3) . . ?
O1 C2 C3 107.0(3) . . ?
C4 C2 C3 114.4(3) . . ?
O1 C2 H2 109.3 . . ?
C4 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
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 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 N1 P1 126.5(2) . . ?
C1 N1 H1N 116.8 . . ?
P1 N1 H1N 116.8 . . ?
N1 C1 N2 116.0(2) . . ?
N1 C1 S2 124.4(2) . . ?
N2 C1 S2 119.6(2) . . ?
C1 N2 C11 130.6(2) . . ?
C1 N2 H2N 114.7 . . ?
C11 N2 H2N 114.7 . . ?
N12 C11 C16 123.6(3) . . ?
N12 C11 N2 118.7(2) . . ?
C16 C11 N2 117.7(2) . . ?
C15 C16 C11 117.4(3) . . ?
C15 C16 H16 121.3 . . ?
C11 C16 H16 121.3 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N12 C13 C14 122.3(3) . . ?
N12 C13 N3 112.9(2) . . ?
C14 C13 N3 124.8(3) . . ?
C11 N12 C13 117.9(2) . . ?
C8 N3 C13 120.8(3) . . ?
N3 C8 C21 121.2(3) . . ?
N3 C8 H8 119.4 . . ?
C21 C8 H8 119.4 . . ?
C26 C21 C22 118.5(3) . . ?
C26 C21 C8 119.5(3) . . ?
C22 C21 C8 122.0(3) . . ?
C25 C26 C21 121.1(3) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C26 C25 C24 119.4(3) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C23 C24 C25 121.0(3) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
O3 C22 C23 118.5(3) . . ?
O3 C22 C21 121.8(3) . . ?
C23 C22 C21 119.7(3) . . ?
C22 O3 H3 109.5 . . ?
C31 O4 H4 109.5 . . ?
O4 C31 C32 117.41(17) . . ?
O4 C31 C36 122.59(17) . . ?
C32 C31 C36 120.0 . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 C35 120.0 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C31 120.0 . . ?
C35 C36 C37 119.5(2) . . ?
C31 C36 C37 120.5(2) . . ?
O5 C37 C36 124.5(3) . . ?
O5 C37 H37 117.8 . . ?
C36 C37 H37 117.8 . . ?

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 O2 C5 128.5(2) . . . . ?
N1 P1 O2 C5 -132.7(2) . . . . ?
S1 P1 O2 C5 -0.4(2) . . . . ?
P1 O2 C5 C7 -98.5(3) . . . . ?
P1 O2 C5 C6 139.0(2) . . . . ?
O2 P1 O1 C2 -80.5(2) . . . . ?
N1 P1 O1 C2 173.0(2) . . . . ?
S1 P1 O1 C2 47.4(2) . . . . ?
P1 O1 C2 C4 -118.1(3) . . . . ?
P1 O1 C2 C3 118.7(2) . . . . ?
O2 P1 N1 C1 62.4(3) . . . . ?
O1 P1 N1 C1 169.0(2) . . . . ?
S1 P1 N1 C1 -67.4(3) . . . . ?
P1 N1 C1 N2 -173.1(2) . . . . ?
P1 N1 C1 S2 6.5(4) . . . . ?
N1 C1 N2 C11 8.4(4) . . . . ?
S2 C1 N2 C11 -171.1(2) . . . . ?
C1 N2 C11 N12 -8.4(4) . . . . ?
C1 N2 C11 C16 170.1(3) . . . . ?
N12 C11 C16 C15 0.9(4) . . . . ?
N2 C11 C16 C15 -177.5(2) . . . . ?
C11 C16 C15 C14 0.0(4) . . . . ?
C16 C15 C14 C13 -0.9(4) . . . . ?
C15 C14 C13 N12 1.1(4) . . . . ?
C15 C14 C13 N3 178.3(3) . . . . ?
C16 C11 N12 C13 -0.7(4) . . . . ?
N2 C11 N12 C13 177.6(2) . . . . ?
C14 C13 N12 C11 -0.3(4) . . . . ?
N3 C13 N12 C11 -177.8(2) . . . . ?
N12 C13 N3 C8 -162.7(2) . . . . ?
C14 C13 N3 C8 19.9(4) . . . . ?
C13 N3 C8 C21 -177.5(3) . . . . ?
N3 C8 C21 C26 179.2(3) . . . . ?
N3 C8 C21 C22 -0.8(5) . . . . ?
C22 C21 C26 C25 -0.5(5) . . . . ?
C8 C21 C26 C25 179.5(3) . . . . ?
C21 C26 C25 C24 -0.2(5) . . . . ?
C26 C25 C24 C23 0.4(5) . . . . ?
C25 C24 C23 C22 0.1(5) . . . . ?
C24 C23 C22 O3 179.9(3) . . . . ?
C24 C23 C22 C21 -0.8(5) . . . . ?
C26 C21 C22 O3 -179.7(3) . . . . ?
C8 C21 C22 O3 0.3(5) . . . . ?
C26 C21 C22 C23 0.9(4) . . . . ?
C8 C21 C22 C23 -179.0(3) . . . . ?
O4 C31 C32 C33 -179.9(2) . . . . ?
C36 C31 C32 C33 0.0 . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C31 0.0 . . . . ?
C34 C35 C36 C37 179.4(2) . . . . ?
O4 C31 C36 C35 179.9(2) . . . . ?
C32 C31 C36 C35 0.0 . . . . ?
O4 C31 C36 C37 0.5(3) . . . . ?
C32 C31 C36 C37 -179.4(2) . . . . ?
C35 C36 C37 O5 -179.9(3) . . . . ?
C31 C36 C37 O5 -0.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.933
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.933
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 980849'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 Cl N4 O3 P S2'
_chemical_formula_sum            'C19 H24 Cl N4 O3 P S2'
_chemical_formula_weight         486.96

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'
Cl Cl 0.1484 0.1585 '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                   8.5874(7)
_cell_length_b                   11.9114(14)
_cell_length_c                   12.8574(15)
_cell_angle_alpha                98.428(10)
_cell_angle_beta                 109.104(9)
_cell_angle_gamma                96.547(8)
_cell_volume                     1210.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5765
_cell_measurement_theta_min      2.1926
_cell_measurement_theta_max      25.7288

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_T_min  0.76019
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '120 images, ΔΦ 2.0°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10918
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.78
_reflns_number_total             4261
_reflns_number_gt                3525
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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 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)+(0.0545P)²+0.7010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4261
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.52280(10) 0.17644(6) 0.27090(6) 0.0597(2) Uani 1 1 d . . .
P1 P 0.34010(8) 0.19862(5) 0.14500(5) 0.04015(18) Uani 1 1 d . . .
O2 O 0.3577(2) 0.17803(15) 0.02680(15) 0.0497(4) Uani 1 1 d . . .
C5 C 0.5159(4) 0.2105(3) 0.0092(3) 0.0663(8) Uani 1 1 d . . .
H5 H 0.6084 0.1950 0.0711 0.080 Uiso 1 1 calc R . .
C6 C 0.5431(6) 0.3355(4) 0.0051(4) 0.1115(17) Uani 1 1 d . . .
H6B H 0.4486 0.3520 -0.0517 0.167 Uiso 1 1 calc R . .
H6C H 0.6422 0.3544 -0.0124 0.167 Uiso 1 1 calc R . .
H6A H 0.5560 0.3805 0.0766 0.167 Uiso 1 1 calc R . .
C7 C 0.5021(7) 0.1344(4) -0.0972(4) 0.1142(18) Uani 1 1 d . . .
H7A H 0.4758 0.0553 -0.0921 0.171 Uiso 1 1 calc R . .
H7B H 0.6065 0.1468 -0.1097 0.171 Uiso 1 1 calc R . .
H7C H 0.4151 0.1518 -0.1586 0.171 Uiso 1 1 calc R . .
O1 O 0.1689(2) 0.11841(15) 0.11437(14) 0.0480(4) Uani 1 1 d . . .
C2 C 0.0973(4) 0.0948(3) 0.2001(3) 0.0592(7) Uani 1 1 d . . .
H2 H 0.1591 0.1485 0.2713 0.071 Uiso 1 1 calc R . .
C4 C 0.1146(6) -0.0264(4) 0.2142(4) 0.1048(15) Uani 1 1 d . . .
H4B H 0.0499 -0.0787 0.1451 0.157 Uiso 1 1 calc R . .
H4C H 0.0748 -0.0438 0.2727 0.157 Uiso 1 1 calc R . .
H4A H 0.2301 -0.0344 0.2338 0.157 Uiso 1 1 calc R . .
C3 C -0.0800(5) 0.1121(4) 0.1582(4) 0.0924(13) Uani 1 1 d . . .
H3A H -0.0838 0.1888 0.1438 0.139 Uiso 1 1 calc R . .
H3B H -0.1298 0.1015 0.2137 0.139 Uiso 1 1 calc R . .
H3C H -0.1407 0.0573 0.0901 0.139 Uiso 1 1 calc R . .
N1 N 0.3128(3) 0.33621(16) 0.17305(16) 0.0414(5) Uani 1 1 d . . .
H1N H 0.3781 0.3755 0.2373 0.050 Uiso 1 1 calc R . .
C1 C 0.2033(3) 0.3943(2) 0.1096(2) 0.0418(6) Uani 1 1 d . . .
S2 S 0.05476(10) 0.33306(6) -0.01367(6) 0.0629(2) Uani 1 1 d . . .
N2 N 0.2201(3) 0.50863(16) 0.14994(16) 0.0420(5) Uani 1 1 d . . .
H2N H 0.1493 0.5428 0.1073 0.050 Uiso 1 1 calc R . .
C11 C 0.3317(3) 0.5810(2) 0.24847(19) 0.0403(5) Uani 1 1 d . . .
C16 C 0.3071(4) 0.6944(2) 0.2700(2) 0.0506(6) Uani 1 1 d . . .
H16 H 0.2208 0.7209 0.2198 0.061 Uiso 1 1 calc R . .
C15 C 0.4131(4) 0.7656(2) 0.3667(2) 0.0586(7) Uani 1 1 d . . .
H15 H 0.3997 0.8418 0.3831 0.070 Uiso 1 1 calc R . .
C14 C 0.5408(4) 0.7241(2) 0.4405(2) 0.0561(7) Uani 1 1 d . . .
H14 H 0.6125 0.7712 0.5073 0.067 Uiso 1 1 calc R . .
C13 C 0.5588(3) 0.6113(2) 0.4123(2) 0.0431(6) Uani 1 1 d . . .
N12 N 0.4552(3) 0.53941(17) 0.31725(16) 0.0405(5) Uani 1 1 d . . .
N3 N 0.6893(3) 0.57155(19) 0.48801(17) 0.0468(5) Uani 1 1 d . . .
C8 C 0.7275(3) 0.4730(2) 0.4638(2) 0.0478(6) Uani 1 1 d . . .
H8 H 0.6687 0.4267 0.3937 0.057 Uiso 1 1 calc R . .
C21 C 0.8613(3) 0.4317(2) 0.5438(2) 0.0484(6) Uani 1 1 d . . .
C22 C 0.9564(4) 0.4984(3) 0.6500(2) 0.0537(7) Uani 1 1 d . . .
C23 C 1.0788(4) 0.4537(3) 0.7253(2) 0.0709(9) Uani 1 1 d . . .
H23 H 1.1411 0.4978 0.7959 0.085 Uiso 1 1 calc R . .
C24 C 1.1081(4) 0.3446(4) 0.6957(3) 0.0732(9) Uani 1 1 d . . .
H24 H 1.1894 0.3147 0.7463 0.088 Uiso 1 1 calc R . .
C25 C 1.0168(4) 0.2799(3) 0.5909(3) 0.0637(8) Uani 1 1 d . . .
C26 C 0.8957(4) 0.3222(3) 0.5155(2) 0.0562(7) Uani 1 1 d . . .
H26 H 0.8359 0.2774 0.4448 0.067 Uiso 1 1 calc R . .
O3 O 0.9310(3) 0.6055(2) 0.68230(16) 0.0690(6) Uani 1 1 d . . .
H3 H 0.8568 0.6223 0.6311 0.104 Uiso 1 1 calc R . .
Cl1 Cl 1.05589(14) 0.14221(9) 0.55394(11) 0.0962(3) Uani 1 1 d . . .


_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 P1 1.9259(10) . ?
P1 O1 1.5557(18) . ?
P1 O2 1.5628(18) . ?
P1 N1 1.6855(19) . ?
O2 C5 1.468(3) . ?
C5 C7 1.488(5) . ?
C5 C6 1.492(5) . ?
C5 H5 0.9800 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C6 H6A 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O1 C2 1.472(3) . ?
C2 C3 1.489(5) . ?
C2 C4 1.500(5) . ?
C2 H2 0.9800 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 H4A 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
N1 C1 1.357(3) . ?
N1 H1N 0.8600 . ?
C1 N2 1.357(3) . ?
C1 S2 1.672(2) . ?
N2 C11 1.401(3) . ?
N2 H2N 0.8600 . ?
C11 N12 1.337(3) . ?
C11 C16 1.392(3) . ?
C16 C15 1.368(4) . ?
C16 H16 0.9300 . ?
C15 C14 1.388(4) . ?
C15 H15 0.9300 . ?
C14 C13 1.379(4) . ?
C14 H14 0.9300 . ?
C13 N12 1.351(3) . ?
C13 N3 1.404(3) . ?
N3 C8 1.276(3) . ?
C8 C21 1.458(4) . ?
C8 H8 0.9300 . ?
C21 C26 1.393(4) . ?
C21 C22 1.403(4) . ?
C22 O3 1.347(4) . ?
C22 C23 1.392(4) . ?
C23 C24 1.374(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.375(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.370(4) . ?
C25 Cl1 1.740(3) . ?
C26 H26 0.9300 . ?
O3 H3 0.8200 . ?

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 O2 98.35(10) . . ?
O1 P1 N1 108.34(10) . . ?
O2 P1 N1 107.15(10) . . ?
O1 P1 S1 117.27(8) . . ?
O2 P1 S1 117.93(8) . . ?
N1 P1 S1 107.08(8) . . ?
C5 O2 P1 123.06(18) . . ?
O2 C5 C7 105.7(3) . . ?
O2 C5 C6 110.2(3) . . ?
C7 C5 C6 113.0(3) . . ?
O2 C5 H5 109.3 . . ?
C7 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
H6B C6 H6A 109.5 . . ?
H6C C6 H6A 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 O1 P1 121.98(17) . . ?
O1 C2 C3 106.8(3) . . ?
O1 C2 C4 106.9(3) . . ?
C3 C2 C4 113.2(3) . . ?
O1 C2 H2 110.0 . . ?
C3 C2 H2 110.0 . . ?
C4 C2 H2 110.0 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
H4B C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
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 . . ?
C1 N1 P1 129.77(17) . . ?
C1 N1 H1N 115.1 . . ?
P1 N1 H1N 115.1 . . ?
N1 C1 N2 116.7(2) . . ?
N1 C1 S2 123.57(18) . . ?
N2 C1 S2 119.77(18) . . ?
C1 N2 C11 131.7(2) . . ?
C1 N2 H2N 114.1 . . ?
C11 N2 H2N 114.1 . . ?
N12 C11 C16 123.0(2) . . ?
N12 C11 N2 119.5(2) . . ?
C16 C11 N2 117.5(2) . . ?
C15 C16 C11 118.2(3) . . ?
C15 C16 H16 120.9 . . ?
C11 C16 H16 120.9 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C13 C14 C15 118.3(2) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
N12 C13 C14 122.7(2) . . ?
N12 C13 N3 120.1(2) . . ?
C14 C13 N3 117.2(2) . . ?
C11 N12 C13 117.8(2) . . ?
C8 N3 C13 121.8(2) . . ?
N3 C8 C21 121.3(2) . . ?
N3 C8 H8 119.3 . . ?
C21 C8 H8 119.3 . . ?
C26 C21 C22 118.3(3) . . ?
C26 C21 C8 119.6(2) . . ?
C22 C21 C8 122.0(3) . . ?
O3 C22 C23 118.5(3) . . ?
O3 C22 C21 121.5(3) . . ?
C23 C22 C21 120.0(3) . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.7(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 Cl1 119.7(3) . . ?
C24 C25 Cl1 119.3(3) . . ?
C25 C26 C21 120.7(3) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C22 O3 H3 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
O1 P1 O2 C5 -164.8(2) . . . . ?
N1 P1 O2 C5 83.0(2) . . . . ?
S1 P1 O2 C5 -37.8(2) . . . . ?
P1 O2 C5 C7 155.7(3) . . . . ?
P1 O2 C5 C6 -81.9(3) . . . . ?
O2 P1 O1 C2 173.52(19) . . . . ?
N1 P1 O1 C2 -75.2(2) . . . . ?
S1 P1 O1 C2 46.1(2) . . . . ?
P1 O1 C2 C3 131.6(2) . . . . ?
P1 O1 C2 C4 -107.0(3) . . . . ?
O1 P1 N1 C1 -54.6(2) . . . . ?
O2 P1 N1 C1 50.6(2) . . . . ?
S1 P1 N1 C1 178.0(2) . . . . ?
P1 N1 C1 N2 -174.17(18) . . . . ?
P1 N1 C1 S2 4.9(3) . . . . ?
N1 C1 N2 C11 -0.5(4) . . . . ?
S2 C1 N2 C11 -179.7(2) . . . . ?
C1 N2 C11 N12 4.9(4) . . . . ?
C1 N2 C11 C16 -174.9(3) . . . . ?
N12 C11 C16 C15 -0.9(4) . . . . ?
N2 C11 C16 C15 178.9(3) . . . . ?
C11 C16 C15 C14 -0.2(4) . . . . ?
C16 C15 C14 C13 1.2(4) . . . . ?
C15 C14 C13 N12 -1.4(4) . . . . ?
C15 C14 C13 N3 179.7(2) . . . . ?
C16 C11 N12 C13 0.8(4) . . . . ?
N2 C11 N12 C13 -179.0(2) . . . . ?
C14 C13 N12 C11 0.4(4) . . . . ?
N3 C13 N12 C11 179.3(2) . . . . ?
N12 C13 N3 C8 8.9(4) . . . . ?
C14 C13 N3 C8 -172.1(3) . . . . ?
C13 N3 C8 C21 -178.9(2) . . . . ?
N3 C8 C21 C26 178.0(3) . . . . ?
N3 C8 C21 C22 -1.1(4) . . . . ?
C26 C21 C22 O3 179.2(2) . . . . ?
C8 C21 C22 O3 -1.7(4) . . . . ?
C26 C21 C22 C23 -1.5(4) . . . . ?
C8 C21 C22 C23 177.6(3) . . . . ?
O3 C22 C23 C24 179.8(3) . . . . ?
C21 C22 C23 C24 0.5(5) . . . . ?
C22 C23 C24 C25 0.5(5) . . . . ?
C23 C24 C25 C26 -0.5(5) . . . . ?
C23 C24 C25 Cl1 179.6(3) . . . . ?
C24 C25 C26 C21 -0.6(5) . . . . ?
Cl1 C25 C26 C21 179.4(2) . . . . ?
C22 C21 C26 C25 1.6(4) . . . . ?
C8 C21 C26 C25 -177.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.915
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.934
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 980850'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 Br N4 O3 P S2'
_chemical_formula_sum            'C19 H24 Br N4 O3 P S2'
_chemical_formula_weight         531.42

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'
Br Br -0.2901 2.4595 '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                   8.5957(13)
_cell_length_b                   11.821(2)
_cell_length_c                   12.807(2)
_cell_angle_alpha                98.558(15)
_cell_angle_beta                 108.643(15)
_cell_angle_gamma                97.790(15)
_cell_volume                     1195.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2742
_cell_measurement_theta_min      1.7110
_cell_measurement_theta_max      25.2389

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow-orange
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    1.987
_exptl_absorpt_correction_T_min  0.70214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku Ultra 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '79 images, ΔΦ 3.0°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8518
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.29
_reflns_number_total             4077
_reflns_number_gt                3618
_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 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)+(0.0562P)²+1.0846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4077
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Br1 Br -0.55991(5) 0.85434(3) 0.45156(4) 0.04739(15) Uani 1 1 d . . .
C25 C -0.5145(4) 0.7049(3) 0.4098(3) 0.0320(7) Uani 1 1 d . . .
C24 C -0.6059(4) 0.6370(3) 0.3039(3) 0.0375(8) Uani 1 1 d . . .
H24 H -0.6904 0.6653 0.2522 0.045 Uiso 1 1 calc R . .
C23 C -0.5733(4) 0.5284(3) 0.2743(3) 0.0369(8) Uani 1 1 d . . .
H23 H -0.6366 0.4814 0.2022 0.044 Uiso 1 1 calc R . .
C22 C -0.4483(4) 0.4865(3) 0.3491(2) 0.0294(7) Uani 1 1 d . . .
C21 C -0.3532(4) 0.5570(3) 0.4561(2) 0.0241(6) Uani 1 1 d . . .
C26 C -0.3906(4) 0.6658(3) 0.4851(3) 0.0278(7) Uani 1 1 d . . .
H26 H -0.3301 0.7132 0.5575 0.033 Uiso 1 1 calc R . .
O3 O -0.4203(3) 0.3807(2) 0.31629(18) 0.0354(5) Uani 1 1 d . . .
H3 H -0.3442 0.3649 0.3689 0.053 Uiso 1 1 calc R . .
C8 C -0.2185(4) 0.5187(3) 0.5353(2) 0.0261(6) Uani 1 1 d . . .
H8 H -0.1580 0.5675 0.6070 0.031 Uiso 1 1 calc R . .
N3 N -0.1797(3) 0.4190(2) 0.50971(19) 0.0246(5) Uani 1 1 d . . .
C13 C -0.0487(4) 0.3821(3) 0.5856(2) 0.0232(6) Uani 1 1 d . . .
C14 C -0.0265(4) 0.2694(3) 0.5558(2) 0.0281(7) Uani 1 1 d . . .
H14 H -0.0972 0.2206 0.4862 0.034 Uiso 1 1 calc R . .
C15 C 0.1003(4) 0.2290(3) 0.6290(3) 0.0296(7) Uani 1 1 d . . .
H15 H 0.1160 0.1515 0.6108 0.036 Uiso 1 1 calc R . .
C16 C 0.2033(4) 0.3017(3) 0.7283(2) 0.0260(6) Uani 1 1 d . . .
H16 H 0.2911 0.2759 0.7799 0.031 Uiso 1 1 calc R . .
C11 C 0.1748(4) 0.4148(2) 0.7509(2) 0.0195(6) Uani 1 1 d . . .
N12 N 0.0513(3) 0.4544(2) 0.68256(19) 0.0216(5) Uani 1 1 d . . .
N2 N 0.2832(3) 0.4882(2) 0.85122(19) 0.0226(5) Uani 1 1 d . . .
H2N H 0.3562 0.4542 0.8945 0.027 Uiso 1 1 calc R . .
C1 C 0.2956(4) 0.6030(2) 0.8935(2) 0.0221(6) Uani 1 1 d . . .
S2 S 0.44106(11) 0.66586(7) 1.01889(6) 0.0342(2) Uani 1 1 d . . .
N1 N 0.1856(3) 0.6595(2) 0.83051(19) 0.0221(5) Uani 1 1 d . . .
H1N H 0.1172 0.6176 0.7652 0.027 Uiso 1 1 calc R . .
P1 P 0.16054(9) 0.79882(6) 0.85902(6) 0.02011(18) Uani 1 1 d . . .
S1 S -0.01969(10) 0.81971(7) 0.73216(6) 0.0296(2) Uani 1 1 d . . .
O2 O 0.3334(3) 0.88041(17) 0.89099(16) 0.0238(4) Uani 1 1 d . . .
C5 C 0.4079(4) 0.9028(3) 0.8053(3) 0.0303(7) Uani 1 1 d . . .
H5 H 0.3461 0.8448 0.7335 0.036 Uiso 1 1 calc R . .
C7 C 0.3880(6) 1.0237(3) 0.7867(4) 0.0502(10) Uani 1 1 d . . .
H7A H 0.2688 1.0269 0.7591 0.075 Uiso 1 1 calc R . .
H7B H 0.4380 1.0426 0.7310 0.075 Uiso 1 1 calc R . .
H7C H 0.4444 1.0801 0.8579 0.075 Uiso 1 1 calc R . .
C6 C 0.5844(5) 0.8870(3) 0.8496(3) 0.0448(9) Uani 1 1 d . . .
H6B H 0.6453 0.9446 0.9195 0.067 Uiso 1 1 calc R . .
H6C H 0.6379 0.8977 0.7938 0.067 Uiso 1 1 calc R . .
H6A H 0.5862 0.8082 0.8648 0.067 Uiso 1 1 calc R . .
O1 O 0.1403(3) 0.82026(18) 0.97729(16) 0.0257(4) Uani 1 1 d . . .
C2 C -0.0192(4) 0.7865(3) 0.9929(3) 0.0336(7) Uani 1 1 d . . .
H2 H -0.1122 0.7988 0.9275 0.040 Uiso 1 1 calc R . .
C4 C -0.0095(7) 0.8671(4) 1.0980(4) 0.0645(14) Uani 1 1 d . . .
H4B H 0.0767 0.8516 1.1629 0.097 Uiso 1 1 calc R . .
H4C H -0.1180 0.8541 1.1086 0.097 Uiso 1 1 calc R . .
H4A H 0.0192 0.9482 1.0913 0.097 Uiso 1 1 calc R . .
C3 C -0.0454(6) 0.6608(3) 1.0005(4) 0.0525(10) Uani 1 1 d . . .
H3A H -0.0491 0.6125 0.9302 0.079 Uiso 1 1 calc R . .
H3B H -0.1513 0.6391 1.0128 0.079 Uiso 1 1 calc R . .
H3C H 0.0471 0.6483 1.0634 0.079 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
Br1 C25 1.897(3) . ?
C25 C26 1.374(5) . ?
C25 C24 1.388(5) . ?
C24 C23 1.374(5) . ?
C24 H24 0.9500 . ?
C23 C22 1.394(5) . ?
C23 H23 0.9500 . ?
C22 O3 1.338(4) . ?
C22 C21 1.414(4) . ?
C21 C26 1.394(4) . ?
C21 C8 1.450(4) . ?
C26 H26 0.9500 . ?
O3 H3 0.8400 . ?
C8 N3 1.291(4) . ?
C8 H8 0.9500 . ?
N3 C13 1.401(4) . ?
C13 N12 1.346(4) . ?
C13 C14 1.387(4) . ?
C14 C15 1.384(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9500 . ?
C16 C11 1.397(4) . ?
C16 H16 0.9500 . ?
C11 N12 1.332(4) . ?
C11 N2 1.398(4) . ?
N2 C1 1.362(4) . ?
N2 H2N 0.8800 . ?
C1 N1 1.355(4) . ?
C1 S2 1.674(3) . ?
N1 P1 1.690(2) . ?
N1 H1N 0.8800 . ?
P1 O2 1.553(2) . ?
P1 O1 1.567(2) . ?
P1 S1 1.9273(11) . ?
O2 C5 1.475(4) . ?
C5 C6 1.489(5) . ?
C5 C7 1.506(5) . ?
C5 H5 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C6 H6A 0.9800 . ?
O1 C2 1.459(4) . ?
C2 C3 1.496(5) . ?
C2 C4 1.501(5) . ?
C2 H2 1.0000 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 H4A 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 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
C26 C25 C24 121.0(3) . . ?
C26 C25 Br1 119.3(3) . . ?
C24 C25 Br1 119.7(3) . . ?
C23 C24 C25 119.5(3) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
O3 C22 C23 118.6(3) . . ?
O3 C22 C21 121.8(3) . . ?
C23 C22 C21 119.6(3) . . ?
C26 C21 C22 118.7(3) . . ?
C26 C21 C8 119.7(3) . . ?
C22 C21 C8 121.6(3) . . ?
C25 C26 C21 120.5(3) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C22 O3 H3 109.5 . . ?
N3 C8 C21 120.9(3) . . ?
N3 C8 H8 119.6 . . ?
C21 C8 H8 119.6 . . ?
C8 N3 C13 121.1(2) . . ?
N12 C13 C14 122.1(3) . . ?
N12 C13 N3 120.8(3) . . ?
C14 C13 N3 117.1(3) . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 117.8(3) . . ?
C15 C16 H16 121.1 . . ?
C11 C16 H16 121.1 . . ?
N12 C11 C16 123.4(3) . . ?
N12 C11 N2 119.7(2) . . ?
C16 C11 N2 116.9(3) . . ?
C11 N12 C13 118.1(2) . . ?
C1 N2 C11 131.2(3) . . ?
C1 N2 H2N 114.4 . . ?
C11 N2 H2N 114.4 . . ?
N1 C1 N2 116.9(3) . . ?
N1 C1 S2 123.8(2) . . ?
N2 C1 S2 119.3(2) . . ?
C1 N1 P1 129.5(2) . . ?
C1 N1 H1N 115.3 . . ?
P1 N1 H1N 115.3 . . ?
O2 P1 O1 98.33(11) . . ?
O2 P1 N1 108.11(12) . . ?
O1 P1 N1 107.44(12) . . ?
O2 P1 S1 117.54(9) . . ?
O1 P1 S1 117.70(9) . . ?
N1 P1 S1 107.02(9) . . ?
C5 O2 P1 121.58(18) . . ?
O2 C5 C6 106.5(3) . . ?
O2 C5 C7 106.9(3) . . ?
C6 C5 C7 114.8(3) . . ?
O2 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
C7 C5 H5 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
H6B C6 H6A 109.5 . . ?
H6C C6 H6A 109.5 . . ?
C2 O1 P1 122.70(19) . . ?
O1 C2 C3 109.8(3) . . ?
O1 C2 C4 105.7(3) . . ?
C3 C2 C4 113.0(3) . . ?
O1 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C4 C2 H2 109.4 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
H4B C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
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 . . ?

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
C26 C25 C24 C23 0.7(5) . . . . ?
Br1 C25 C24 C23 -179.5(2) . . . . ?
C25 C24 C23 C22 -0.7(5) . . . . ?
C24 C23 C22 O3 -179.6(3) . . . . ?
C24 C23 C22 C21 -0.5(5) . . . . ?
O3 C22 C21 C26 -179.2(3) . . . . ?
C23 C22 C21 C26 1.8(4) . . . . ?
O3 C22 C21 C8 1.0(4) . . . . ?
C23 C22 C21 C8 -178.1(3) . . . . ?
C24 C25 C26 C21 0.6(5) . . . . ?
Br1 C25 C26 C21 -179.2(2) . . . . ?
C22 C21 C26 C25 -1.8(4) . . . . ?
C8 C21 C26 C25 178.0(3) . . . . ?
C26 C21 C8 N3 -178.9(3) . . . . ?
C22 C21 C8 N3 1.0(4) . . . . ?
C21 C8 N3 C13 179.4(2) . . . . ?
C8 N3 C13 N12 -7.0(4) . . . . ?
C8 N3 C13 C14 173.7(3) . . . . ?
N12 C13 C14 C15 1.4(4) . . . . ?
N3 C13 C14 C15 -179.3(3) . . . . ?
C13 C14 C15 C16 -1.3(5) . . . . ?
C14 C15 C16 C11 -0.1(4) . . . . ?
C15 C16 C11 N12 1.5(4) . . . . ?
C15 C16 C11 N2 -178.7(3) . . . . ?
C16 C11 N12 C13 -1.4(4) . . . . ?
N2 C11 N12 C13 178.7(2) . . . . ?
C14 C13 N12 C11 0.0(4) . . . . ?
N3 C13 N12 C11 -179.3(2) . . . . ?
N12 C11 N2 C1 -4.8(4) . . . . ?
C16 C11 N2 C1 175.3(3) . . . . ?
C11 N2 C1 N1 0.3(4) . . . . ?
C11 N2 C1 S2 179.6(2) . . . . ?
N2 C1 N1 P1 177.4(2) . . . . ?
S2 C1 N1 P1 -1.8(4) . . . . ?
C1 N1 P1 O2 52.7(3) . . . . ?
C1 N1 P1 O1 -52.5(3) . . . . ?
C1 N1 P1 S1 -179.8(2) . . . . ?
O1 P1 O2 C5 -174.0(2) . . . . ?
N1 P1 O2 C5 74.5(2) . . . . ?
S1 P1 O2 C5 -46.7(2) . . . . ?
P1 O2 C5 C6 -132.0(2) . . . . ?
P1 O2 C5 C7 104.9(3) . . . . ?
O2 P1 O1 C2 165.1(2) . . . . ?
N1 P1 O1 C2 -82.8(2) . . . . ?
S1 P1 O1 C2 37.9(2) . . . . ?
P1 O1 C2 C3 83.8(3) . . . . ?
P1 O1 C2 C4 -154.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.933
_diffrn_reflns_theta_full        25.29
_diffrn_measured_fraction_theta_full 0.933
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.077
_database_code_depnum_ccdc_archive 'CCDC 980851'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 Cl2 N4 O3 P S2'
_chemical_formula_sum            'C19 H23 Cl2 N4 O3 P S2'
_chemical_formula_weight         521.40

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'
Cl Cl 0.1484 0.1585 '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           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                   9.0052(8)
_cell_length_b                   11.7572(10)
_cell_length_c                   12.3225(11)
_cell_angle_alpha                98.558(7)
_cell_angle_beta                 106.445(7)
_cell_angle_gamma                97.060(7)
_cell_volume                     1218.47(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    27751
_cell_measurement_theta_min      3.375
_cell_measurement_theta_max      26.825

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8317
_exptl_absorpt_correction_T_max  0.9537
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
;
 ;
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator  'Genix 3D multilayer optics'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23183
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         26.46
_reflns_number_total             4997
_reflns_number_gt                4205
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL97

_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)+(0.0507P)²+0.7299P] 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         4997
_refine_ls_number_parameters     291
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.100
_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
P1 P 0.31375(8) 0.19311(5) 0.63652(5) 0.02625(16) Uani 1 1 d . . .
S1 S 0.47934(8) 0.16991(6) 0.76518(6) 0.03705(18) Uani 1 1 d . . .
O1 O 0.1499(2) 0.11529(14) 0.60816(15) 0.0310(4) Uani 1 1 d . . .
C2 C 0.0778(3) 0.0962(2) 0.6992(2) 0.0372(6) Uani 1 1 d D . .
H2 H 0.1367 0.1531 0.7721 0.045 Uiso 1 1 calc R . .
C3 C -0.0880(4) 0.1168(3) 0.6580(3) 0.0536(8) Uani 1 1 d D . .
H3A H -0.0877 0.1979 0.6475 0.080 Uiso 1 1 calc R . .
H3B H -0.1411 0.1023 0.7152 0.080 Uiso 1 1 calc R . .
H3C H -0.1438 0.0638 0.5844 0.080 Uiso 1 1 calc R . .
C4 C 0.0900(5) -0.0260(3) 0.7177(3) 0.0566(9) Uani 1 1 d D . .
H4A H 0.2010 -0.0338 0.7438 0.085 Uiso 1 1 calc R . .
H4B H 0.0363 -0.0813 0.6452 0.085 Uiso 1 1 calc R . .
H4C H 0.0406 -0.0427 0.7763 0.085 Uiso 1 1 calc R . .
O2 O 0.3361(2) 0.16753(15) 0.51439(15) 0.0324(4) Uani 1 1 d . A .
C5 C 0.4813(4) 0.2167(3) 0.4927(3) 0.0481(7) Uani 1 1 d D . .
H5 H 0.5709 0.2222 0.5642 0.058 Uiso 0.659(13) 1 calc PR A 1
H5' H 0.5529 0.2676 0.5657 0.058 Uiso 0.341(13) 1 calc PR A 2
C6 C 0.4830(7) 0.3311(4) 0.4641(5) 0.0465(16) Uiso 0.659(13) 1 d PD A 1
H6A H 0.4742 0.3866 0.5287 0.070 Uiso 0.659(13) 1 calc PR A 1
H6B H 0.3943 0.3286 0.3953 0.070 Uiso 0.659(13) 1 calc PR A 1
H6C H 0.5818 0.3560 0.4487 0.070 Uiso 0.659(13) 1 calc PR A 1
C7 C 0.4976(11) 0.1205(6) 0.3994(7) 0.075(2) Uiso 0.659(13) 1 d PD A 1
H7A H 0.5002 0.0469 0.4277 0.113 Uiso 0.659(13) 1 calc PR A 1
H7B H 0.5952 0.1430 0.3815 0.113 Uiso 0.659(13) 1 calc PR A 1
H7C H 0.4078 0.1103 0.3295 0.113 Uiso 0.659(13) 1 calc PR A 1
C6' C 0.417(2) 0.2961(16) 0.4060(16) 0.094(5) Uiso 0.341(13) 1 d PD A 2
H6'1 H 0.3629 0.3517 0.4403 0.142 Uiso 0.341(13) 1 calc PR A 2
H6'2 H 0.3436 0.2476 0.3349 0.142 Uiso 0.341(13) 1 calc PR A 2
H6'3 H 0.5050 0.3388 0.3880 0.142 Uiso 0.341(13) 1 calc PR A 2
C7' C 0.5664(14) 0.1362(8) 0.4501(11) 0.049(3) Uiso 0.341(13) 1 d PD A 2
H7'1 H 0.5202 0.0566 0.4512 0.074 Uiso 0.341(13) 1 calc PR A 2
H7'2 H 0.6763 0.1536 0.4989 0.074 Uiso 0.341(13) 1 calc PR A 2
H7'3 H 0.5613 0.1430 0.3709 0.074 Uiso 0.341(13) 1 calc PR A 2
N1 N 0.2939(3) 0.33401(18) 0.66359(18) 0.0275(4) Uani 1 1 d . . .
H1N H 0.358(4) 0.372(3) 0.717(3) 0.041(9) Uiso 1 1 d . . .
C1 C 0.1896(3) 0.3920(2) 0.6017(2) 0.0262(5) Uani 1 1 d . . .
S2 S 0.05078(8) 0.32967(5) 0.47888(6) 0.03728(18) Uani 1 1 d . . .
N2 N 0.2037(2) 0.50792(17) 0.64442(18) 0.0263(4) Uani 1 1 d . . .
H2N H 0.140(3) 0.539(2) 0.609(3) 0.028(7) Uiso 1 1 d . . .
C11 C 0.3117(3) 0.58188(19) 0.74077(19) 0.0234(5) Uani 1 1 d . . .
N12 N 0.4287(2) 0.54016(16) 0.80644(16) 0.0230(4) Uani 1 1 d . . .
C13 C 0.5313(3) 0.6147(2) 0.8982(2) 0.0245(5) Uani 1 1 d . . .
C14 C 0.5200(3) 0.7307(2) 0.9265(2) 0.0300(5) Uani 1 1 d . . .
H14 H 0.5945 0.7807 0.9919 0.036 Uiso 1 1 calc R . .
C15 C 0.3973(3) 0.7722(2) 0.8570(2) 0.0327(6) Uani 1 1 d . . .
H15 H 0.3870 0.8518 0.8742 0.039 Uiso 1 1 calc R . .
C16 C 0.2907(3) 0.6985(2) 0.7634(2) 0.0283(5) Uani 1 1 d . . .
H16 H 0.2050 0.7253 0.7153 0.034 Uiso 1 1 calc R . .
N3 N 0.6565(2) 0.57410(17) 0.97062(17) 0.0255(4) Uani 1 1 d . . .
C8 C 0.6859(3) 0.4714(2) 0.9445(2) 0.0267(5) Uani 1 1 d . . .
H8 H 0.6205 0.4205 0.8758 0.032 Uiso 1 1 calc R . .
Cl1 Cl 1.17351(8) 0.55557(7) 1.30807(6) 0.04286(19) Uani 1 1 d . . .
Cl2 Cl 1.01627(10) 0.14596(6) 1.01026(7) 0.0487(2) Uani 1 1 d . . .
O3 O 0.8936(2) 0.61306(15) 1.15636(16) 0.0316(4) Uani 1 1 d . . .
H3 H 0.820(5) 0.624(3) 1.105(3) 0.058(11) Uiso 1 1 d . . .
C21 C 0.8173(3) 0.4319(2) 1.0183(2) 0.0266(5) Uani 1 1 d . . .
C22 C 0.9167(3) 0.5052(2) 1.1205(2) 0.0268(5) Uani 1 1 d . . .
C23 C 1.0447(3) 0.4638(2) 1.1867(2) 0.0301(5) Uani 1 1 d . . .
C24 C 1.0727(3) 0.3532(2) 1.1539(2) 0.0334(6) Uani 1 1 d . . .
H24 H 1.1590 0.3256 1.2005 0.040 Uiso 1 1 calc R . .
C25 C 0.9747(3) 0.2831(2) 1.0531(2) 0.0329(6) Uani 1 1 d . . .
C26 C 0.8492(3) 0.3211(2) 0.9850(2) 0.0300(5) Uani 1 1 d . . .
H26 H 0.7839 0.2720 0.9151 0.036 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 1.5549(19) . ?
P1 O2 1.5646(19) . ?
P1 N1 1.682(2) . ?
P1 S1 1.9240(9) . ?
O1 C2 1.476(3) . ?
C2 C3 1.498(4) . ?
C2 C4 1.501(4) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
O2 C5 1.474(4) . ?
C5 C7' 1.419(9) . ?
C5 C6 1.440(5) . ?
C5 C7 1.541(7) . ?
C5 C6' 1.557(11) . ?
C5 H5 1.0000 . ?
C5 H5' 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6' H6'1 0.9800 . ?
C6' H6'2 0.9800 . ?
C6' H6'3 0.9800 . ?
C7' H7'1 0.9800 . ?
C7' H7'2 0.9800 . ?
C7' H7'3 0.9800 . ?
N1 C1 1.354(3) . ?
N1 H1N 0.77(3) . ?
C1 N2 1.363(3) . ?
C1 S2 1.663(2) . ?
N2 C11 1.394(3) . ?
N2 H2N 0.78(3) . ?
C11 N12 1.330(3) . ?
C11 C16 1.404(3) . ?
N12 C13 1.347(3) . ?
C13 C14 1.380(3) . ?
C13 N3 1.408(3) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.369(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N3 C8 1.282(3) . ?
C8 C21 1.447(3) . ?
C8 H8 0.9500 . ?
Cl1 C23 1.725(3) . ?
Cl2 C25 1.740(3) . ?
O3 C22 1.340(3) . ?
O3 H3 0.82(4) . ?
C21 C26 1.395(3) . ?
C21 C22 1.408(3) . ?
C22 C23 1.398(3) . ?
C23 C24 1.378(4) . ?
C24 C25 1.378(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.371(4) . ?
C26 H26 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 O2 98.45(10) . . ?
O1 P1 N1 108.61(11) . . ?
O2 P1 N1 107.54(11) . . ?
O1 P1 S1 117.37(8) . . ?
O2 P1 S1 117.44(8) . . ?
N1 P1 S1 106.83(8) . . ?
C2 O1 P1 121.58(16) . . ?
O1 C2 C3 107.0(2) . . ?
O1 C2 C4 107.1(2) . . ?
C3 C2 C4 113.6(3) . . ?
O1 C2 H2 109.7 . . ?
C3 C2 H2 109.7 . . ?
C4 C2 H2 109.7 . . ?
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 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 O2 P1 121.81(17) . . ?
C7' C5 C6 121.4(5) . . ?
C7' C5 O2 117.1(5) . . ?
C6 C5 O2 114.8(3) . . ?
C6 C5 C7 115.2(4) . . ?
O2 C5 C7 102.9(4) . . ?
C7' C5 C6' 112.6(8) . . ?
O2 C5 C6' 101.1(7) . . ?
C6 C5 H5 107.8 . . ?
O2 C5 H5 107.8 . . ?
C7 C5 H5 107.8 . . ?
C7' C5 H5' 108.5 . . ?
O2 C5 H5' 108.5 . . ?
C6' C5 H5' 108.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C6' H6'1 109.5 . . ?
C5 C6' H6'2 109.5 . . ?
H6'1 C6' H6'2 109.5 . . ?
C5 C6' H6'3 109.5 . . ?
H6'1 C6' H6'3 109.5 . . ?
H6'2 C6' H6'3 109.5 . . ?
C5 C7' H7'1 109.5 . . ?
C5 C7' H7'2 109.5 . . ?
H7'1 C7' H7'2 109.5 . . ?
C5 C7' H7'3 109.5 . . ?
H7'1 C7' H7'3 109.5 . . ?
H7'2 C7' H7'3 109.5 . . ?
C1 N1 P1 129.62(18) . . ?
C1 N1 H1N 115(2) . . ?
P1 N1 H1N 115(2) . . ?
N1 C1 N2 116.5(2) . . ?
N1 C1 S2 123.64(18) . . ?
N2 C1 S2 119.84(17) . . ?
C1 N2 C11 131.6(2) . . ?
C1 N2 H2N 115(2) . . ?
C11 N2 H2N 113(2) . . ?
N12 C11 N2 119.4(2) . . ?
N12 C11 C16 123.1(2) . . ?
N2 C11 C16 117.5(2) . . ?
C11 N12 C13 117.6(2) . . ?
N12 C13 C14 123.2(2) . . ?
N12 C13 N3 119.5(2) . . ?
C14 C13 N3 117.3(2) . . ?
C13 C14 C15 118.3(2) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 118.0(2) . . ?
C15 C16 H16 121.0 . . ?
C11 C16 H16 121.0 . . ?
C8 N3 C13 121.5(2) . . ?
N3 C8 C21 120.9(2) . . ?
N3 C8 H8 119.5 . . ?
C21 C8 H8 119.5 . . ?
C22 O3 H3 105(3) . . ?
C26 C21 C22 119.7(2) . . ?
C26 C21 C8 119.3(2) . . ?
C22 C21 C8 121.0(2) . . ?
O3 C22 C23 119.0(2) . . ?
O3 C22 C21 122.5(2) . . ?
C23 C22 C21 118.5(2) . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 Cl1 119.82(19) . . ?
C22 C23 Cl1 119.0(2) . . ?
C25 C24 C23 119.4(2) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C26 C25 C24 121.2(2) . . ?
C26 C25 Cl2 120.0(2) . . ?
C24 C25 Cl2 118.8(2) . . ?
C25 C26 C21 120.0(2) . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?

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
O2 P1 O1 C2 173.04(18) . . . . ?
N1 P1 O1 C2 -75.2(2) . . . . ?
S1 P1 O1 C2 46.1(2) . . . . ?
P1 O1 C2 C3 131.7(2) . . . . ?
P1 O1 C2 C4 -106.2(2) . . . . ?
O1 P1 O2 C5 -177.0(2) . . . . ?
N1 P1 O2 C5 70.4(2) . . . . ?
S1 P1 O2 C5 -50.0(2) . . . . ?
P1 O2 C5 C7' 121.1(6) . . . . ?
P1 O2 C5 C6 -87.1(4) . . . . ?
P1 O2 C5 C7 147.0(4) . . . . ?
P1 O2 C5 C6' -116.2(8) . . . . ?
O1 P1 N1 C1 -49.6(3) . . . . ?
O2 P1 N1 C1 56.0(3) . . . . ?
S1 P1 N1 C1 -177.1(2) . . . . ?
P1 N1 C1 N2 -178.82(19) . . . . ?
P1 N1 C1 S2 0.5(4) . . . . ?
N1 C1 N2 C11 2.6(4) . . . . ?
S2 C1 N2 C11 -176.8(2) . . . . ?
C1 N2 C11 N12 2.1(4) . . . . ?
C1 N2 C11 C16 -178.1(3) . . . . ?
N2 C11 N12 C13 179.5(2) . . . . ?
C16 C11 N12 C13 -0.4(4) . . . . ?
C11 N12 C13 C14 0.1(4) . . . . ?
C11 N12 C13 N3 179.6(2) . . . . ?
N12 C13 C14 C15 0.0(4) . . . . ?
N3 C13 C14 C15 -179.6(2) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
N12 C11 C16 C15 0.7(4) . . . . ?
N2 C11 C16 C15 -179.2(2) . . . . ?
N12 C13 N3 C8 7.9(3) . . . . ?
C14 C13 N3 C8 -172.6(2) . . . . ?
C13 N3 C8 C21 178.4(2) . . . . ?
N3 C8 C21 C26 -177.7(2) . . . . ?
N3 C8 C21 C22 -0.2(4) . . . . ?
C26 C21 C22 O3 179.1(2) . . . . ?
C8 C21 C22 O3 1.7(4) . . . . ?
C26 C21 C22 C23 -0.6(4) . . . . ?
C8 C21 C22 C23 -178.1(2) . . . . ?
O3 C22 C23 C24 179.5(2) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
O3 C22 C23 Cl1 -3.2(3) . . . . ?
C21 C22 C23 Cl1 176.58(19) . . . . ?
C22 C23 C24 C25 1.2(4) . . . . ?
Cl1 C23 C24 C25 -176.1(2) . . . . ?
C23 C24 C25 C26 -0.3(4) . . . . ?
C23 C24 C25 Cl2 177.5(2) . . . . ?
C24 C25 C26 C21 -1.1(4) . . . . ?
Cl2 C25 C26 C21 -178.9(2) . . . . ?
C22 C21 C26 C25 1.5(4) . . . . ?
C8 C21 C26 C25 179.0(2) . . . . ?

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
N1 H1N N12 0.77(3) 2.04(3) 2.691(3) 142(3) .
N2 H2N S2 0.78(3) 2.57(3) 3.343(2) 171(3) 2_566
O3 H3 N3 0.82(4) 1.83(4) 2.586(3) 152(4) .

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 980852'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6

# start Validation Reply Form
_vrf_PLAT413_I                   
;
PROBLEM: Short Inter XH3 .. XHn     H2L3   ..  H15     ..       1.80 Ang. 
RESPONSE: There is an ethanol molecule disordered 
about a two-fold rotation axis.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C19 H23 Br2 N4 O3 P S2), C H3 O0.5'
_chemical_formula_sum            'C20 H26 Br2 N4 O3.5 P S2'
_chemical_formula_weight         633.36

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'
Br Br -0.2901 2.4595 '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                   25.4932(13)
_cell_length_b                   8.2482(5)
_cell_length_c                   25.1957(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.280(4)
_cell_angle_gamma                90.00
_cell_volume                     5195.6(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17752
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      26.4

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2552
_exptl_absorpt_coefficient_mu    3.374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5108
_exptl_absorpt_correction_T_max  0.7511
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
;
 ;
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator  'Genix 3D multilayer optics'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29742
_diffrn_reflns_av_R_equivalents  0.1051
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4580
_reflns_number_gt                3458
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL97

_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)+(0.0747P)²+0.0000P] 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         4580
_refine_ls_number_parameters     304
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.028
_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
Br1 Br 0.09465(2) 0.80277(8) 0.50531(2) 0.04089(19) Uani 1 1 d . . .
Br2 Br 0.16948(3) 0.85950(9) 0.30848(2) 0.0570(2) Uani 1 1 d . . .
P1 P 0.37128(5) 0.27146(18) 0.34691(5) 0.0279(3) Uani 1 1 d . . .
S1 S 0.30594(6) 0.3942(2) 0.33246(5) 0.0383(4) Uani 1 1 d . . .
S2 S 0.47077(6) 0.0438(2) 0.41578(5) 0.0372(4) Uani 1 1 d . . .
N1 N 0.38280(16) 0.2231(6) 0.41307(16) 0.0287(10) Uani 1 1 d D . .
H1N H 0.3599(19) 0.262(7) 0.434(2) 0.042(17) Uiso 1 1 d D . .
N2 N 0.42658(17) 0.1319(6) 0.49683(16) 0.0269(10) Uani 1 1 d D . .
H2N H 0.4556(12) 0.087(6) 0.5183(16) 0.019(13) Uiso 1 1 d D . .
N3 N 0.27337(16) 0.4323(5) 0.51777(16) 0.0262(9) Uani 1 1 d . . .
O2 O 0.37353(14) 0.1156(5) 0.31264(13) 0.0314(9) Uani 1 1 d . . .
O1 O 0.42288(15) 0.3561(5) 0.33572(14) 0.0327(9) Uani 1 1 d . . .
O3 O 0.18864(15) 0.5794(5) 0.53207(14) 0.0312(8) Uani 1 1 d D . .
H3 H 0.208(3) 0.496(6) 0.535(3) 0.08(3) Uiso 1 1 d D . .
C1 C 0.4246(2) 0.1379(7) 0.4424(2) 0.0292(12) Uani 1 1 d . . .
C2 C 0.4375(3) 0.5211(8) 0.3538(3) 0.0440(15) Uani 1 1 d . . .
H2 H 0.4053 0.5757 0.3628 0.053 Uiso 1 1 calc R . .
C4 C 0.4535(5) 0.6084(12) 0.3078(4) 0.089(3) Uani 1 1 d . . .
H4A H 0.4237 0.6076 0.2766 0.133 Uiso 1 1 calc R . .
H4B H 0.4846 0.5545 0.2980 0.133 Uiso 1 1 calc R . .
H4C H 0.4628 0.7207 0.3184 0.133 Uiso 1 1 calc R . .
C3 C 0.4807(3) 0.5167(10) 0.4039(3) 0.0570(18) Uani 1 1 d . . .
H3A H 0.4677 0.4586 0.4327 0.086 Uiso 1 1 calc R . .
H3B H 0.4904 0.6277 0.4158 0.086 Uiso 1 1 calc R . .
H3C H 0.5122 0.4609 0.3959 0.086 Uiso 1 1 calc R . .
C5 C 0.3285(2) 0.0048(8) 0.2960(2) 0.0427(15) Uani 1 1 d . . .
H5 H 0.2946 0.0688 0.2867 0.051 Uiso 1 1 calc R . .
C6 C 0.3246(4) -0.1092(11) 0.3405(3) 0.085(3) Uani 1 1 d . . .
H6A H 0.3177 -0.0484 0.3718 0.127 Uiso 1 1 calc R . .
H6B H 0.3583 -0.1691 0.3506 0.127 Uiso 1 1 calc R . .
H6C H 0.2953 -0.1856 0.3284 0.127 Uiso 1 1 calc R . .
C7 C 0.3390(3) -0.0789(9) 0.2461(3) 0.0503(17) Uani 1 1 d . . .
H7A H 0.3405 0.0018 0.2179 0.075 Uiso 1 1 calc R . .
H7B H 0.3102 -0.1563 0.2331 0.075 Uiso 1 1 calc R . .
H7C H 0.3732 -0.1368 0.2547 0.075 Uiso 1 1 calc R . .
C8 C 0.2668(2) 0.4937(6) 0.4697(2) 0.0275(11) Uani 1 1 d . . .
H8 H 0.2920 0.4701 0.4475 0.033 Uiso 1 1 calc R . .
C11 C 0.3926(2) 0.1933(6) 0.52954(19) 0.0253(11) Uani 1 1 d . . .
N12 N 0.35033(16) 0.2825(5) 0.50696(15) 0.0237(9) Uani 1 1 d . . .
C13 C 0.31808(19) 0.3350(6) 0.53894(19) 0.0237(11) Uani 1 1 d . . .
C14 C 0.3260(2) 0.3000(7) 0.5934(2) 0.0303(12) Uani 1 1 d . . .
H14 H 0.3012 0.3356 0.6146 0.036 Uiso 1 1 calc R . .
C15 C 0.3709(2) 0.2116(7) 0.6166(2) 0.0326(12) Uani 1 1 d . . .
H15 H 0.3783 0.1897 0.6544 0.039 Uiso 1 1 calc R . .
C16 C 0.4045(2) 0.1564(7) 0.5844(2) 0.0301(12) Uani 1 1 d . . .
H16 H 0.4352 0.0941 0.5992 0.036 Uiso 1 1 calc R . .
C21 C 0.2221(2) 0.5970(6) 0.4495(2) 0.0260(11) Uani 1 1 d . . .
C22 C 0.1847(2) 0.6375(7) 0.4822(2) 0.0263(11) Uani 1 1 d . . .
C23 C 0.1432(2) 0.7415(7) 0.4606(2) 0.0307(12) Uani 1 1 d . . .
C24 C 0.1377(2) 0.8057(7) 0.4098(2) 0.0353(13) Uani 1 1 d . . .
H24 H 0.1088 0.8764 0.3961 0.042 Uiso 1 1 calc R . .
C25 C 0.1749(2) 0.7658(7) 0.3785(2) 0.0372(13) Uani 1 1 d . . .
C26 C 0.2165(2) 0.6649(7) 0.3975(2) 0.0329(13) Uani 1 1 d . . .
H26 H 0.2418 0.6401 0.3756 0.040 Uiso 1 1 calc R . .
O2L O 0.0363(6) 0.6861(16) 0.2970(6) 0.116(5) Uiso 0.50 1 d PD . .
H1L H 0.0674 0.7270 0.2997 0.174 Uiso 0.50 1 d PR . .
C1L C 0.0133(4) 0.5547(12) 0.2662(4) 0.040(3) Uiso 0.50 1 d PD . .
H1L1 H 0.0202 0.5663 0.2291 0.048 Uiso 0.50 1 calc PR . .
H1L2 H -0.0259 0.5594 0.2637 0.048 Uiso 0.50 1 calc PR . .
C2L C 0.0325(7) 0.3916(16) 0.2873(7) 0.080(5) Uiso 0.50 1 d PD . .
H2L1 H 0.0156 0.3079 0.2620 0.120 Uiso 0.50 1 calc PR . .
H2L2 H 0.0230 0.3742 0.3227 0.120 Uiso 0.50 1 calc PR . .
H2L3 H 0.0714 0.3858 0.2909 0.120 Uiso 0.50 1 calc PR . .


_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
Br1 C23 1.896(5) . ?
Br2 C25 1.906(5) . ?
P1 O2 1.556(4) . ?
P1 O1 1.563(4) . ?
P1 N1 1.683(4) . ?
P1 S1 1.9221(19) . ?
S2 C1 1.657(5) . ?
N1 C1 1.367(7) . ?
N1 H1N 0.912(10) . ?
N2 C1 1.363(6) . ?
N2 C11 1.402(6) . ?
N2 H2N 0.906(10) . ?
N3 C8 1.292(7) . ?
N3 C13 1.411(7) . ?
O2 C5 1.463(7) . ?
O1 C2 1.460(8) . ?
O3 C22 1.330(6) . ?
O3 H3 0.839(10) . ?
C2 C4 1.489(10) . ?
C2 C3 1.505(9) . ?
C2 H2 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C5 C6 1.480(10) . ?
C5 C7 1.505(8) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C21 1.434(7) . ?
C8 H8 0.9500 . ?
C11 N12 1.337(7) . ?
C11 C16 1.390(7) . ?
N12 C13 1.331(6) . ?
C13 C14 1.379(7) . ?
C14 C15 1.387(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.367(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.406(7) . ?
C21 C22 1.417(7) . ?
C22 C23 1.388(8) . ?
C23 C24 1.368(8) . ?
C24 C25 1.387(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.358(8) . ?
C26 H26 0.9500 . ?
O2L C1L 1.393(3) . ?
O2L H1L 0.8514 . ?
C1L C2L 1.492(3) . ?
C1L H1L1 0.9900 . ?
C1L H1L2 0.9900 . ?
C2L H2L1 0.9800 . ?
C2L H2L2 0.9800 . ?
C2L H2L3 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
O2 P1 O1 98.4(2) . . ?
O2 P1 N1 109.6(2) . . ?
O1 P1 N1 107.1(2) . . ?
O2 P1 S1 117.04(16) . . ?
O1 P1 S1 117.34(17) . . ?
N1 P1 S1 106.81(16) . . ?
C1 N1 P1 128.6(3) . . ?
C1 N1 H1N 113(4) . . ?
P1 N1 H1N 118(4) . . ?
C1 N2 C11 132.3(4) . . ?
C1 N2 H2N 119(3) . . ?
C11 N2 H2N 109(3) . . ?
C8 N3 C13 121.6(4) . . ?
C5 O2 P1 124.2(3) . . ?
C2 O1 P1 122.2(3) . . ?
C22 O3 H3 108(6) . . ?
N2 C1 N1 115.7(4) . . ?
N2 C1 S2 120.1(4) . . ?
N1 C1 S2 124.2(4) . . ?
O1 C2 C4 107.4(6) . . ?
O1 C2 C3 109.9(5) . . ?
C4 C2 C3 113.5(6) . . ?
O1 C2 H2 108.6 . . ?
C4 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
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 . . ?
O2 C5 C6 110.2(6) . . ?
O2 C5 C7 105.5(4) . . ?
C6 C5 C7 112.9(6) . . ?
O2 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C7 C5 H5 109.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C21 120.9(4) . . ?
N3 C8 H8 119.6 . . ?
C21 C8 H8 119.6 . . ?
N12 C11 C16 123.0(4) . . ?
N12 C11 N2 119.2(4) . . ?
C16 C11 N2 117.8(5) . . ?
C13 N12 C11 117.6(4) . . ?
N12 C13 C14 123.2(5) . . ?
N12 C13 N3 120.4(4) . . ?
C14 C13 N3 116.4(4) . . ?
C13 C14 C15 118.5(5) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C16 C15 C14 119.1(5) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 118.5(5) . . ?
C15 C16 H16 120.7 . . ?
C11 C16 H16 120.7 . . ?
C26 C21 C22 119.3(5) . . ?
C26 C21 C8 119.8(4) . . ?
C22 C21 C8 120.8(4) . . ?
O3 C22 C23 120.2(4) . . ?
O3 C22 C21 121.9(5) . . ?
C23 C22 C21 117.8(5) . . ?
C24 C23 C22 122.4(5) . . ?
C24 C23 Br1 119.6(4) . . ?
C22 C23 Br1 117.9(4) . . ?
C23 C24 C25 119.0(5) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C26 C25 C24 121.2(5) . . ?
C26 C25 Br2 119.0(4) . . ?
C24 C25 Br2 119.7(4) . . ?
C25 C26 C21 120.2(5) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C1L O2L H1L 129.7 . . ?
O2L C1L C2L 115.5(13) . . ?
O2L C1L H1L1 108.4 . . ?
C2L C1L H1L1 108.4 . . ?
O2L C1L H1L2 108.4 . . ?
C2L C1L H1L2 108.4 . . ?
H1L1 C1L H1L2 107.5 . . ?
C1L C2L H2L1 109.5 . . ?
C1L C2L H2L2 109.5 . . ?
H2L1 C2L H2L2 109.5 . . ?
C1L C2L H2L3 109.5 . . ?
H2L1 C2L H2L3 109.5 . . ?
H2L2 C2L H2L3 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
O2 P1 N1 C1 52.9(6) . . . . ?
O1 P1 N1 C1 -52.8(6) . . . . ?
S1 P1 N1 C1 -179.3(5) . . . . ?
O1 P1 O2 C5 -164.2(4) . . . . ?
N1 P1 O2 C5 84.2(5) . . . . ?
S1 P1 O2 C5 -37.6(5) . . . . ?
O2 P1 O1 C2 172.9(4) . . . . ?
N1 P1 O1 C2 -73.5(4) . . . . ?
S1 P1 O1 C2 46.5(4) . . . . ?
C11 N2 C1 N1 2.2(9) . . . . ?
C11 N2 C1 S2 -177.2(5) . . . . ?
P1 N1 C1 N2 173.2(4) . . . . ?
P1 N1 C1 S2 -7.5(8) . . . . ?
P1 O1 C2 C4 -134.5(6) . . . . ?
P1 O1 C2 C3 101.6(5) . . . . ?
P1 O2 C5 C6 -82.3(7) . . . . ?
P1 O2 C5 C7 155.5(4) . . . . ?
C13 N3 C8 C21 -177.8(5) . . . . ?
C1 N2 C11 N12 -3.4(9) . . . . ?
C1 N2 C11 C16 175.9(6) . . . . ?
C16 C11 N12 C13 -1.1(8) . . . . ?
N2 C11 N12 C13 178.1(5) . . . . ?
C11 N12 C13 C14 -0.9(8) . . . . ?
C11 N12 C13 N3 178.8(5) . . . . ?
C8 N3 C13 N12 -10.8(8) . . . . ?
C8 N3 C13 C14 168.9(5) . . . . ?
N12 C13 C14 C15 2.8(8) . . . . ?
N3 C13 C14 C15 -176.8(5) . . . . ?
C13 C14 C15 C16 -2.8(9) . . . . ?
C14 C15 C16 C11 1.0(9) . . . . ?
N12 C11 C16 C15 1.0(8) . . . . ?
N2 C11 C16 C15 -178.2(5) . . . . ?
N3 C8 C21 C26 178.8(5) . . . . ?
N3 C8 C21 C22 1.5(8) . . . . ?
C26 C21 C22 O3 -178.7(5) . . . . ?
C8 C21 C22 O3 -1.4(8) . . . . ?
C26 C21 C22 C23 1.0(8) . . . . ?
C8 C21 C22 C23 178.3(5) . . . . ?
O3 C22 C23 C24 179.4(5) . . . . ?
C21 C22 C23 C24 -0.4(8) . . . . ?
O3 C22 C23 Br1 2.2(7) . . . . ?
C21 C22 C23 Br1 -177.5(4) . . . . ?
C22 C23 C24 C25 -0.1(9) . . . . ?
Br1 C23 C24 C25 177.0(4) . . . . ?
C23 C24 C25 C26 0.0(9) . . . . ?
C23 C24 C25 Br2 -177.8(4) . . . . ?
C24 C25 C26 C21 0.7(9) . . . . ?
Br2 C25 C26 C21 178.5(4) . . . . ?
C22 C21 C26 C25 -1.2(8) . . . . ?
C8 C21 C26 C25 -178.5(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
N1 H1N N12 0.912(10) 1.92(4) 2.700(5) 143(5) .
N2 H2N S2 0.906(10) 2.495(12) 3.397(4) 174(4) 5_656
O3 H3 N3 0.839(10) 1.88(6) 2.564(5) 138(8) .
O2L H1L Br2 0.85 2.79 3.642(14) 179.6 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.451
_refine_diff_density_min         -1.176
_refine_diff_density_rms         0.099
_database_code_depnum_ccdc_archive 'CCDC 980853'
