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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cpd11
_database_code_depnum_ccdc_archive 'CCDC 1467310'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   5.8693(4)
_cell_length_b                   8.7664(8)
_cell_length_c                   18.5843(13)
_cell_angle_alpha                95.209(7)
_cell_angle_beta                 89.257(6)
_cell_angle_gamma                109.426(7)
_cell_volume                     897.90(13)

_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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C14 H19 N4 O2 P1 S2 
# Dc =      1.37 Fooo =    388.00 Mu =      3.99 M =    370.44
# Found Formula = C14 H19 N4 O2 P1 S2 
# Dc =      1.37 FOOO =    388.00 Mu =      3.99 M =    370.44

_chemical_formula_sum            'C14 H19 N4 O2 P1 S2'
_chemical_formula_moiety         'C12 H11 N4 P S2, 2(C H4 O)'
_chemical_compound_source        ?
_chemical_formula_weight         370.44


_cell_measurement_reflns_used    2123
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.399

# Sheldrick geometric approximatio 0.91 0.92 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.92
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'XRED (Stoe & Cie 1996)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      180
_diffrn_reflns_number            8299
_reflns_number_total             4732
_diffrn_reflns_av_R_equivalents  0.052
# Number of reflections without Friedels Law is 6089 
# Number of reflections with Friedels Law is 4732 
# Theoretical number of reflections is about 4803 


_diffrn_reflns_theta_min         3.453
_diffrn_reflns_theta_max         28.998
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        25.808
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              -11
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.32
_refine_diff_density_max         0.42


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_number_parameters     209
_oxford_refine_ls_R_factor_ref   0.0371
_refine_ls_wR_factor_ref         0.0437
_refine_ls_goodness_of_fit_ref   1.0954
_refine_ls_shift/su_max          0.0002290
_refine_ls_shift/su_mean         0.0000223


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4724
_refine_ls_R_factor_all          0.0473
_refine_ls_wR_factor_all         0.0489

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3799
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_gt          0.0452

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.840 0.392 0.410 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
P1 P 0.60779(7) 0.10240(5) 0.14997(2) 0.0173 1.0000 Uani . . . . . .
S1 S 0.05966(7) -0.13928(5) 0.13797(2) 0.0208 1.0000 Uani . . . . . .
S2 S 0.41679(8) -0.05357(6) 0.29606(2) 0.0252 1.0000 Uani . . . . . .
C1 C 0.3618(3) -0.0682(2) 0.11137(9) 0.0178 1.0000 Uani . . . . . .
C2 C 0.3885(3) -0.1699(2) 0.05481(9) 0.0193 1.0000 Uani . . . . . .
C3 C 0.0017(3) -0.29983(19) 0.07048(9) 0.0187 1.0000 Uani . . . . . .
C4 C 0.6446(3) 0.0517(2) 0.23980(9) 0.0186 1.0000 Uani . . . . . .
C5 C 0.8596(3) 0.0933(2) 0.27606(9) 0.0239 1.0000 Uani . . . . . .
C6 C 0.6333(3) -0.0331(3) 0.36301(10) 0.0267 1.0000 Uani . . . . . .
C7 C 0.4694(3) 0.26049(19) 0.16853(9) 0.0179 1.0000 Uani . . . . . .
C8 C 0.2869(3) 0.2725(2) 0.12435(9) 0.0205 1.0000 Uani . . . . . .
C9 C 0.1998(3) 0.4015(2) 0.13570(10) 0.0255 1.0000 Uani . . . . . .
C10 C 0.2975(4) 0.5228(2) 0.19111(11) 0.0314 1.0000 Uani . . . . . .
C11 C 0.4822(4) 0.5143(3) 0.23464(11) 0.0352 1.0000 Uani . . . . . .
C12 C 0.5673(4) 0.3846(2) 0.22385(10) 0.0282 1.0000 Uani . . . . . .
C13 C 0.3841(5) 0.3003(3) 0.42882(14) 0.0470 1.0000 Uani . . . . . .
C15 C -0.0385(6) 0.6069(5) 0.3919(2) 0.0867 1.0000 Uani . . . . . .
N1 N 0.1904(3) -0.29996(17) 0.03135(8) 0.0208 1.0000 Uani . . . . . .
N2 N -0.2197(3) -0.41132(19) 0.05908(9) 0.0257 1.0000 Uani . . . . . .
N3 N 0.8553(3) 0.0473(2) 0.34533(8) 0.0287 1.0000 Uani . . . . . .
N4 N 0.5713(3) -0.0973(3) 0.42585(10) 0.0455 1.0000 Uani . . . . . .
O14 O 0.1844(3) 0.1771(2) 0.45480(8) 0.0450 1.0000 Uani . . . . . .
O16 O 0.0936(4) 0.7107(3) 0.44764(13) 0.0765 1.0000 Uani . . . . . .
H21 H 0.5375 -0.1555 0.0322 0.0241 1.0000 Uiso R . . . . .
H51 H 1.0089 0.1525 0.2558 0.0287 1.0000 Uiso R . . . . .
H81 H 0.2219 0.1918 0.0868 0.0256 1.0000 Uiso R . . . . .
H91 H 0.0765 0.4052 0.1058 0.0308 1.0000 Uiso R . . . . .
H101 H 0.2420 0.6109 0.1980 0.0380 1.0000 Uiso R . . . . .
H111 H 0.5486 0.5970 0.2718 0.0424 1.0000 Uiso R . . . . .
H121 H 0.6914 0.3790 0.2539 0.0345 1.0000 Uiso R . . . . .
H23 H -0.2290 -0.4987 0.0319 0.0315 1.0000 Uiso R . . . . .
H42 H 0.6823 -0.0897 0.4577 0.0540 1.0000 Uiso R . . . . .
H22 H -0.3344 -0.4124 0.0897 0.0326 1.0000 Uiso R . . . . .
H41 H 0.4237 -0.1493 0.4346 0.0545 1.0000 Uiso R . . . . .
H141 H 0.0950 0.1341 0.4212 0.0683 1.0000 Uiso R . . . . .
H161 H 0.0110 0.7384 0.4779 0.1156 1.0000 Uiso R . . . . .
H133 H 0.3376 0.3929 0.4207 0.0709 1.0000 Uiso R . . . . .
H131 H 0.4404 0.2624 0.3841 0.0717 1.0000 Uiso R . . . . .
H153 H -0.1584 0.6481 0.3759 0.1280 1.0000 Uiso R . . . . .
H132 H 0.5153 0.3323 0.4644 0.0718 1.0000 Uiso R . . . . .
H151 H 0.0673 0.5964 0.3537 0.1280 1.0000 Uiso R . . . . .
H152 H -0.1130 0.5035 0.4089 0.1282 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       206(14)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 . C1 . 1.7974(17) yes
P1 . C4 . 1.7999(17) yes
P1 . C7 . 1.8317(17) yes
S1 . C1 . 1.7536(17) yes
S1 . C3 . 1.7441(16) yes
S2 . C4 . 1.7468(17) yes
S2 . C6 . 1.7447(19) yes
C1 . C2 . 1.358(2) yes
C2 . N1 . 1.372(2) yes
C2 . H21 . 0.941 no
C3 . N1 . 1.317(2) yes
C3 . N2 . 1.347(2) yes
C4 . C5 . 1.360(2) yes
C5 . N3 . 1.381(2) yes
C5 . H51 . 0.951 no
C6 . N3 . 1.313(2) yes
C6 . N4 . 1.336(2) yes
C7 . C8 . 1.395(2) yes
C7 . C12 . 1.402(2) yes
C8 . C9 . 1.387(3) yes
C8 . H81 . 0.933 no
C9 . C10 . 1.389(3) yes
C9 . H91 . 0.929 no
C10 . C11 . 1.386(3) yes
C10 . H101 . 0.932 no
C11 . C12 . 1.384(3) yes
C11 . H111 . 0.939 no
C12 . H121 . 0.941 no
C13 . O14 . 1.418(3) yes
C13 . H133 . 0.962 no
C13 . H131 . 0.962 no
C13 . H132 . 0.971 no
C15 . O16 . 1.372(4) yes
C15 . H153 . 0.952 no
C15 . H151 . 0.955 no
C15 . H152 . 0.948 no
N2 . H23 . 0.865 no
N2 . H22 . 0.874 no
N4 . H42 . 0.869 no
N4 . H41 . 0.855 no
O14 . H141 . 0.802 no
O16 . H161 . 0.811 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . P1 . C4 . 104.08(8) yes
C1 . P1 . C7 . 103.11(7) yes
C4 . P1 . C7 . 101.33(8) yes
C1 . S1 . C3 . 89.62(8) yes
C4 . S2 . C6 . 89.78(8) yes
P1 . C1 . S1 . 129.16(9) yes
P1 . C1 . C2 . 122.98(13) yes
S1 . C1 . C2 . 107.83(12) yes
C1 . C2 . N1 . 118.13(15) yes
C1 . C2 . H21 . 122.4 no
N1 . C2 . H21 . 119.4 no
S1 . C3 . N1 . 114.34(12) yes
S1 . C3 . N2 . 122.11(13) yes
N1 . C3 . N2 . 123.54(15) yes
P1 . C4 . S2 . 126.98(10) yes
P1 . C4 . C5 . 124.80(14) yes
S2 . C4 . C5 . 108.21(13) yes
C4 . C5 . N3 . 117.39(16) yes
C4 . C5 . H51 . 122.8 no
N3 . C5 . H51 . 119.8 no
S2 . C6 . N3 . 114.22(14) yes
S2 . C6 . N4 . 121.18(15) yes
N3 . C6 . N4 . 124.60(17) yes
P1 . C7 . C8 . 122.13(13) yes
P1 . C7 . C12 . 119.18(13) yes
C8 . C7 . C12 . 118.28(16) yes
C7 . C8 . C9 . 121.10(16) yes
C7 . C8 . H81 . 119.2 no
C9 . C8 . H81 . 119.7 no
C8 . C9 . C10 . 119.88(17) yes
C8 . C9 . H91 . 119.0 no
C10 . C9 . H91 . 121.1 no
C9 . C10 . C11 . 119.75(17) yes
C9 . C10 . H101 . 119.9 no
C11 . C10 . H101 . 120.3 no
C10 . C11 . C12 . 120.38(18) yes
C10 . C11 . H111 . 119.5 no
C12 . C11 . H111 . 120.1 no
C7 . C12 . C11 . 120.59(17) yes
C7 . C12 . H121 . 119.5 no
C11 . C12 . H121 . 119.9 no
O14 . C13 . H133 . 109.7 no
O14 . C13 . H131 . 111.1 no
H133 . C13 . H131 . 108.6 no
O14 . C13 . H132 . 109.2 no
H133 . C13 . H132 . 109.6 no
H131 . C13 . H132 . 108.6 no
O16 . C15 . H153 . 109.1 no
O16 . C15 . H151 . 109.3 no
H153 . C15 . H151 . 111.3 no
O16 . C15 . H152 . 108.6 no
H153 . C15 . H152 . 110.0 no
H151 . C15 . H152 . 108.5 no
C2 . N1 . C3 . 110.09(14) yes
C3 . N2 . H23 . 116.9 no
C3 . N2 . H22 . 119.7 no
H23 . N2 . H22 . 119.5 no
C5 . N3 . C6 . 110.39(15) yes
C6 . N4 . H42 . 119.9 no
C6 . N4 . H41 . 120.9 no
H42 . N4 . H41 . 119.2 no
C13 . O14 . H141 . 107.8 no
C15 . O16 . H161 . 113.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N2 . H23 . N1 2_545 170.66(6) 0.865 2.105 2.961(3) yes
N4 . H42 . O14 2_656 151.69(7) 0.869 2.121 2.915(3) yes
N4 . H41 . O16 1_545 173.21(11) 0.855 1.944 2.795(3) yes
O14 . H141 . N3 1_455 172.56(8) 0.802 1.920 2.717(3) yes
O16 . H161 . O14 2_566 174.41(10) 0.811 1.946 2.754(3) yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cpd13
_database_code_depnum_ccdc_archive 'CCDC 1467311'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 

Hydrogen atoms could not be located on water molecules
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   15.0238(16)
_cell_length_b                   11.6122(10)
_cell_length_c                   20.9195(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3649.6(3)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  '-P 2ac 2ab '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C9 H14 Cl3 N6 O1 P1 S3 
# Dc =      1.66 Fooo =   1840.00 Mu =      9.43 M =    455.78
# Found Formula = C9 H12 Cl3 N6 O1 P1 S3 
# Dc =      1.65 FOOO =   1840.00 Mu =      9.43 M =    453.76

_chemical_formula_sum            'C9 H14 Cl3 N6 O1 P1 S3'
_chemical_formula_moiety         'C9 H12 N6 P S3, 3(Cl), H2 O'
_chemical_compound_source        ?
_chemical_formula_weight         455.78


_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    150

_exptl_crystal_description       planar
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.080
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.66
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    0.943

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.95
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_method       'φ scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'IPDS (Stoe & Cie, 1996)'
_computing_cell_refinement       'IPDS (Stoe & Cie, 1996)'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            36255
_reflns_number_total             3472
_diffrn_reflns_av_R_equivalents  0.070
# Number of reflections without Friedels Law is 3472 
# Number of reflections with Friedels Law is 0 
# Theoretical number of reflections is about 3581 


_diffrn_reflns_theta_min         2.372
_diffrn_reflns_theta_max         26.001
_diffrn_measured_fraction_theta_max 0.967

_diffrn_reflns_theta_full        25.221
_diffrn_measured_fraction_theta_full 0.972


_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              0
_reflns_limit_h_max              18
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.59
_refine_diff_density_max         2.05


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     0
_refine_ls_number_parameters     190
_oxford_refine_ls_R_factor_ref   0.0583
_refine_ls_wR_factor_ref         0.0697
_refine_ls_goodness_of_fit_ref   1.1163
_refine_ls_shift/su_max          0.0002896
_refine_ls_shift/su_mean         0.0000376


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3472
_refine_ls_R_factor_all          0.0951
_refine_ls_wR_factor_all         0.0933

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1846
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_gt          0.0697

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 1.22 0.656 0.586 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
P1 P 0.47052(10) 0.46040(14) 0.75040(9) 0.0200 1.0000 Uani . . . . . .
S1 S 0.59358(11) 0.62538(15) 0.66612(8) 0.0247 1.0000 Uani . . . . . .
S2 S 0.60544(11) 0.61159(15) 0.83290(8) 0.0239 1.0000 Uani . . . . . .
S3 S 0.35075(11) 0.67099(17) 0.70281(8) 0.0298 1.0000 Uani . . . . . .
C1 C 0.5339(4) 0.4972(6) 0.6809(3) 0.0218 1.0000 Uani . . . . . .
C2 C 0.5346(4) 0.4317(7) 0.6282(3) 0.0278 1.0000 Uani . . . . . .
C3 C 0.6161(4) 0.5810(6) 0.5895(3) 0.0252 1.0000 Uani . . . . . .
C4 C 0.5430(4) 0.4867(6) 0.8177(3) 0.0221 1.0000 Uani . . . . . .
C5 C 0.5406(4) 0.4208(6) 0.8707(3) 0.0228 1.0000 Uani . . . . . .
C6 C 0.6261(5) 0.5644(6) 0.9100(3) 0.0236 1.0000 Uani . . . . . .
C7 C 0.4026(4) 0.5891(6) 0.7624(3) 0.0250 1.0000 Uani . . . . . .
C8 C 0.3774(5) 0.6320(7) 0.8194(3) 0.0326 1.0000 Uani . . . . . .
C9 C 0.3018(4) 0.7577(6) 0.7588(4) 0.0292 1.0000 Uani . . . . . .
N1 N 0.5816(4) 0.4774(5) 0.5782(3) 0.0286 1.0000 Uani . . . . . .
N2 N 0.6623(4) 0.6388(6) 0.5481(3) 0.0366 1.0000 Uani . . . . . .
N3 N 0.5872(4) 0.4650(5) 0.9213(3) 0.0256 1.0000 Uani . . . . . .
N4 N 0.6763(4) 0.6221(6) 0.9507(3) 0.0347 1.0000 Uani . . . . . .
N5 N 0.3246(4) 0.7225(5) 0.8182(3) 0.0289 1.0000 Uani . . . . . .
N6 N 0.2518(4) 0.8481(5) 0.7492(3) 0.0318 1.0000 Uani . . . . . .
O100 O 0.4021(4) 0.5881(5) 0.5497(3) 0.0494 1.0000 Uani . . . . . .
Cl1 Cl 0.30189(12) 0.38732(15) 0.89493(8) 0.0300 1.0000 Uani . . . . . .
Cl2 Cl 0.29955(12) 0.37350(16) 0.60574(8) 0.0332 1.0000 Uani . . . . . .
Cl3 Cl 0.5972(2) 0.1996(2) 0.53048(10) 0.0778 1.0000 Uani . . . . . .
H11 H 0.5887 0.4420 0.5425 0.0334 1.0000 Uiso R . . . . .
H21 H 0.5049 0.3617 0.6256 0.0342 1.0000 Uiso R . . . . .
H22 H 0.6576 0.6231 0.5079 0.0434 1.0000 Uiso R . . . . .
H23 H 0.6869 0.7020 0.5602 0.0432 1.0000 Uiso R . . . . .
H31 H 0.5910 0.4305 0.9576 0.0320 1.0000 Uiso R . . . . .
H41 H 0.6955 0.6896 0.9401 0.0402 1.0000 Uiso R . . . . .
H42 H 0.6739 0.6045 0.9904 0.0403 1.0000 Uiso R . . . . .
H51 H 0.5099 0.3514 0.8729 0.0292 1.0000 Uiso R . . . . .
H52 H 0.3060 0.7562 0.8523 0.0371 1.0000 Uiso R . . . . .
H61 H 0.2423 0.8710 0.7105 0.0374 1.0000 Uiso R . . . . .
H62 H 0.2266 0.8808 0.7815 0.0374 1.0000 Uiso R . . . . .
H81 H 0.3972 0.6010 0.8580 0.0401 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 . C1 . 1.790(7) yes
P1 . C4 . 1.806(7) yes
P1 . C7 . 1.827(7) yes
S1 . C1 . 1.765(7) yes
S1 . C3 . 1.718(7) yes
S2 . C4 . 1.756(7) yes
S2 . C6 . 1.732(6) yes
S3 . C7 . 1.751(6) yes
S3 . C9 . 1.710(7) yes
C1 . C2 . 1.34(1) yes
C2 . N1 . 1.369(9) yes
C2 . H21 . 0.929 no
C3 . N1 . 1.330(9) yes
C3 . N2 . 1.297(9) yes
C4 . C5 . 1.348(10) yes
C5 . N3 . 1.369(9) yes
C5 . H51 . 0.929 no
C6 . N3 . 1.315(9) yes
C6 . N4 . 1.320(9) yes
C7 . C8 . 1.346(9) yes
C8 . N5 . 1.317(9) yes
C8 . H81 . 0.934 no
C9 . N5 . 1.352(9) yes
C9 . N6 . 1.306(9) yes
N1 . H11 . 0.860 no
N2 . H22 . 0.863 no
N2 . H23 . 0.861 no
N3 . H31 . 0.860 no
N4 . H41 . 0.864 no
N4 . H42 . 0.857 no
N5 . H52 . 0.860 no
N6 . H61 . 0.864 no
N6 . H62 . 0.862 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . P1 . C4 . 105.8(3) yes
C1 . P1 . C7 . 102.3(3) yes
C4 . P1 . C7 . 95.2(3) yes
C1 . S1 . C3 . 90.6(3) yes
C4 . S2 . C6 . 90.2(3) yes
C7 . S3 . C9 . 91.3(3) yes
S1 . C1 . P1 . 127.8(4) yes
S1 . C1 . C2 . 109.3(5) yes
P1 . C1 . C2 . 122.5(5) yes
C1 . C2 . N1 . 114.4(6) yes
C1 . C2 . H21 . 122.8 no
N1 . C2 . H21 . 122.8 no
S1 . C3 . N1 . 111.1(5) yes
S1 . C3 . N2 . 125.0(6) yes
N1 . C3 . N2 . 124.0(6) yes
P1 . C4 . S2 . 127.1(4) yes
P1 . C4 . C5 . 122.0(5) yes
S2 . C4 . C5 . 109.5(5) yes
C4 . C5 . N3 . 114.2(6) yes
C4 . C5 . H51 . 123.0 no
N3 . C5 . H51 . 122.7 no
S2 . C6 . N3 . 111.5(5) yes
S2 . C6 . N4 . 122.8(6) yes
N3 . C6 . N4 . 125.7(6) yes
P1 . C7 . S3 . 126.5(4) yes
P1 . C7 . C8 . 125.6(5) yes
S3 . C7 . C8 . 107.7(5) yes
C7 . C8 . N5 . 116.6(7) yes
C7 . C8 . H81 . 122.3 no
N5 . C8 . H81 . 121.1 no
S3 . C9 . N5 . 110.0(5) yes
S3 . C9 . N6 . 128.0(6) yes
N5 . C9 . N6 . 121.9(7) yes
C2 . N1 . C3 . 114.6(6) yes
C2 . N1 . H11 . 122.9 no
C3 . N1 . H11 . 122.5 no
C3 . N2 . H22 . 119.8 no
C3 . N2 . H23 . 118.3 no
H22 . N2 . H23 . 120.2 no
C5 . N3 . C6 . 114.7(6) yes
C5 . N3 . H31 . 122.8 no
C6 . N3 . H31 . 122.6 no
C6 . N4 . H41 . 119.1 no
C6 . N4 . H42 . 118.8 no
H41 . N4 . H42 . 118.6 no
C9 . N5 . C8 . 114.3(6) yes
C9 . N5 . H52 . 122.9 no
C8 . N5 . H52 . 122.8 no
C9 . N6 . H61 . 119.1 no
C9 . N6 . H62 . 119.1 no
H61 . N6 . H62 . 121.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N1 . H11 . O100 2_666 161.4(3) 0.860 1.964 2.793(10) yes


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cpd15
_database_code_depnum_ccdc_archive 'CCDC 1467312'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;

_audit_creation_date             2016-04-21T17:31:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H23 N2 O2 P S'
_chemical_formula_sum            'C21 H23 N2 O2 P S'
_chemical_formula_weight         398.44
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7642(9)
_cell_length_b                   10.8437(11)
_cell_length_c                   12.1558(12)
_cell_angle_alpha                94.396(5)
_cell_angle_beta                 106.808(5)
_cell_angle_gamma                109.396(5)
_cell_volume                     1023.87(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.35
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.125
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.979

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_number            20382
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3739
_reflns_number_gt                3487
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       APEX2
_computing_cell_refinement       'APEX2 and SAINT'
_computing_data_reduction        SAINT
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0350P)²+0.6654P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3739
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.44807(5) 0.04626(4) 0.19529(3) 0.02561(11) Uani 1 1 d . . .
P1 P 0.52208(5) 0.32265(4) 0.34987(3) 0.02348(11) Uani 1 1 d . . .
O2 O 0.86843(15) 0.45441(12) 0.20102(11) 0.0377(3) Uani 1 1 d . . .
O1 O 1.12115(15) 0.52306(13) 0.34868(11) 0.0405(3) Uani 1 1 d . . .
N1 N 0.77430(16) 0.12059(13) 0.23215(11) 0.0258(3) Uani 1 1 d . . .
N2 N 0.6109(2) -0.08566(14) 0.10461(13) 0.0353(3) Uani 1 1 d . . .
C10 C 0.3564(2) 0.33352(15) 0.22209(13) 0.0238(3) Uani 1 1 d . . .
C2 C 0.74816(19) 0.21869(15) 0.29394(13) 0.0226(3) Uani 1 1 d . . .
C4 C 0.90297(19) 0.33847(15) 0.36345(13) 0.0271(3) Uani 1 1 d . . .
H4A H 0.9997 0.3097 0.3974 0.033 Uiso 1 1 calc R . .
H4B H 0.8786 0.3787 0.4291 0.033 Uiso 1 1 calc R . .
C16 C 0.3983(2) 0.24041(16) 0.43957(13) 0.0256(3) Uani 1 1 d . . .
C11 C 0.4134(2) 0.42011(16) 0.15061(15) 0.0315(4) Uani 1 1 d . . .
H11 H 0.5327 0.4693 0.1696 0.038 Uiso 1 1 calc R . .
C3 C 0.6272(2) 0.02334(15) 0.17512(13) 0.0255(3) Uani 1 1 d . . .
C15 C 0.1815(2) 0.26374(17) 0.19360(14) 0.0316(4) Uani 1 1 d . . .
H15 H 0.1405 0.2043 0.2412 0.038 Uiso 1 1 calc R . .
C1 C 0.58408(19) 0.19935(14) 0.28768(13) 0.0224(3) Uani 1 1 d . . .
C5 C 0.9566(2) 0.44296(16) 0.29281(14) 0.0280(3) Uani 1 1 d . . .
C21 C 0.3367(2) 0.31813(17) 0.49863(14) 0.0309(4) Uani 1 1 d . . .
H21 H 0.3533 0.4064 0.4863 0.037 Uiso 1 1 calc R . .
C9 C 0.4479(3) -0.19569(18) 0.05482(18) 0.0458(5) Uani 1 1 d . . .
H9A H 0.4317 -0.2534 0.112 0.069 Uiso 1 1 calc R . .
H9B H 0.4462 -0.2469 -0.0158 0.069 Uiso 1 1 calc R . .
H9C H 0.3551 -0.1614 0.0344 0.069 Uiso 1 1 calc R . .
C20 C 0.2517(2) 0.2680(2) 0.57493(15) 0.0382(4) Uani 1 1 d . . .
H20 H 0.2104 0.322 0.6144 0.046 Uiso 1 1 calc R . .
C12 C 0.2976(3) 0.43507(17) 0.05217(15) 0.0383(4) Uani 1 1 d . . .
H12 H 0.3377 0.4929 0.0032 0.046 Uiso 1 1 calc R . .
C13 C 0.1246(3) 0.3661(2) 0.02562(15) 0.0405(4) Uani 1 1 d . . .
H13 H 0.045 0.3773 -0.0411 0.049 Uiso 1 1 calc R . .
C19 C 0.2266(3) 0.1398(2) 0.59389(16) 0.0431(5) Uani 1 1 d . . .
H19 H 0.1663 0.1048 0.645 0.052 Uiso 1 1 calc R . .
C18 C 0.2900(3) 0.0633(2) 0.53780(17) 0.0452(5) Uani 1 1 d . . .
H18 H 0.2751 -0.0243 0.5517 0.054 Uiso 1 1 calc R . .
C17 C 0.3755(2) 0.11291(18) 0.46129(15) 0.0360(4) Uani 1 1 d . . .
H17 H 0.4188 0.0591 0.4235 0.043 Uiso 1 1 calc R . .
C14 C 0.0664(2) 0.2804(2) 0.09596(16) 0.0409(4) Uani 1 1 d . . .
H14 H -0.0532 0.2327 0.0772 0.049 Uiso 1 1 calc R . .
C8 C 0.7637(3) -0.1062(2) 0.09717(17) 0.0473(5) Uani 1 1 d . . .
H8A H 0.8619 -0.0213 0.1248 0.071 Uiso 1 1 calc R . .
H8B H 0.7454 -0.1411 0.0157 0.071 Uiso 1 1 calc R . .
H8C H 0.7868 -0.1701 0.146 0.071 Uiso 1 1 calc R . .
C6 C 1.1971(2) 0.6288(2) 0.29064(18) 0.0455(5) Uani 1 1 d . . .
H2A H 1.3236 0.6565 0.3197 0.055 Uiso 1 1 calc R . .
H2B H 1.1555 0.5951 0.2052 0.055 Uiso 1 1 calc R . .
C7 C 1.1502(4) 0.7428(2) 0.3142(2) 0.0743(8) Uani 1 1 d . . .
H1A H 1.0262 0.7178 0.2773 0.111 Uiso 1 1 calc R . .
H1B H 1.2112 0.8166 0.2823 0.111 Uiso 1 1 calc R . .
H1C H 1.1819 0.7707 0.399 0.111 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C3 1.7488(16) . ?
S1 C1 1.7503(15) . ?
P1 C1 1.7943(15) . ?
P1 C16 1.8308(16) . ?
P1 C10 1.8363(16) . ?
O2 C5 1.202(2) . ?
O1 C5 1.3442(19) . ?
O1 C6 1.464(2) . ?
N1 C3 1.313(2) . ?
N1 C2 1.3738(19) . ?
N2 C3 1.347(2) . ?
N2 C9 1.445(2) . ?
N2 C8 1.455(2) . ?
C10 C15 1.387(2) . ?
C10 C11 1.397(2) . ?
C2 C1 1.361(2) . ?
C2 C4 1.497(2) . ?
C4 C5 1.507(2) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C16 C17 1.387(2) . ?
C16 C21 1.397(2) . ?
C11 C12 1.387(3) . ?
C11 H11 0.95 . ?
C15 C14 1.386(2) . ?
C15 H15 0.95 . ?
C21 C20 1.385(2) . ?
C21 H21 0.95 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C20 C19 1.382(3) . ?
C20 H20 0.95 . ?
C12 C13 1.374(3) . ?
C12 H12 0.95 . ?
C13 C14 1.383(3) . ?
C13 H13 0.95 . ?
C19 C18 1.379(3) . ?
C19 H19 0.95 . ?
C18 C17 1.389(3) . ?
C18 H18 0.95 . ?
C17 H17 0.95 . ?
C14 H14 0.95 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C6 C7 1.460(3) . ?
C6 H2A 0.99 . ?
C6 H2B 0.99 . ?
C7 H1A 0.98 . ?
C7 H1B 0.98 . ?
C7 H1C 0.98 . ?

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
C3 S1 C1 89.19(7) . . ?
C1 P1 C16 105.74(7) . . ?
C1 P1 C10 101.62(7) . . ?
C16 P1 C10 103.00(7) . . ?
C5 O1 C6 116.77(13) . . ?
C3 N1 C2 110.12(13) . . ?
C3 N2 C9 121.03(15) . . ?
C3 N2 C8 119.69(15) . . ?
C9 N2 C8 118.07(15) . . ?
C15 C10 C11 118.74(15) . . ?
C15 C10 P1 124.66(12) . . ?
C11 C10 P1 116.60(12) . . ?
C1 C2 N1 117.63(13) . . ?
C1 C2 C4 125.09(14) . . ?
N1 C2 C4 117.29(13) . . ?
C2 C4 C5 113.64(13) . . ?
C2 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C2 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C17 C16 C21 118.29(15) . . ?
C17 C16 P1 125.07(12) . . ?
C21 C16 P1 116.35(12) . . ?
C12 C11 C10 120.72(16) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
N1 C3 N2 123.98(15) . . ?
N1 C3 S1 114.68(11) . . ?
N2 C3 S1 121.33(13) . . ?
C14 C15 C10 120.23(16) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C2 C1 S1 108.38(11) . . ?
C2 C1 P1 124.03(11) . . ?
S1 C1 P1 127.13(9) . . ?
O2 C5 O1 124.55(15) . . ?
O2 C5 C4 126.30(14) . . ?
O1 C5 C4 109.15(13) . . ?
C20 C21 C16 120.80(16) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C19 C20 C21 120.33(16) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C13 C12 C11 119.86(16) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.01(16) . . ?
C12 C13 H13 120 . . ?
C14 C13 H13 120 . . ?
C18 C19 C20 119.29(17) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C18 C17 120.68(18) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C16 C17 C18 120.58(16) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C14 C15 120.44(17) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C6 O1 109.91(18) . . ?
C7 C6 H2A 109.7 . . ?
O1 C6 H2A 109.7 . . ?
C7 C6 H2B 109.7 . . ?
O1 C6 H2B 109.7 . . ?
H2A C6 H2B 108.2 . . ?
C6 C7 H1A 109.5 . . ?
C6 C7 H1B 109.5 . . ?
H1A C7 H1B 109.5 . . ?
C6 C7 H1C 109.5 . . ?
H1A C7 H1C 109.5 . . ?
H1B C7 H1C 109.5 . . ?


# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cpd17
_database_code_depnum_ccdc_archive 'CCDC 1467313'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   10.3954(8)
_cell_length_b                   18.9943(19)
_cell_length_c                   8.6719(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.398(9)
_cell_angle_gamma                90
_cell_volume                     1711.8(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C17 H17 N4 P1 S1 
# Dc =      1.32 Fooo =    712.00 Mu =      2.87 M =    340.39
# Found Formula = C17 H17 N4 P1 S1 
# Dc =      1.32 FOOO =    712.00 Mu =      2.87 M =    340.39

_chemical_formula_sum            'C17 H17 N4 P1 S1'
_chemical_formula_moiety         'C17 H17 N4 P1 S1'
_chemical_compound_source        ?
_chemical_formula_weight         340.39


_cell_measurement_reflns_used    7800
_cell_measurement_theta_min      3
_cell_measurement_theta_max      24
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.287

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  1.0
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'IPDS (Stoe & Cie, 1996)'
_computing_cell_refinement       'IPDS (Stoe & Cie, 1996)'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      180
_diffrn_reflns_number            13354
_reflns_number_total             3278
_diffrn_reflns_av_R_equivalents  0.077
# Number of reflections without Friedels Law is 3278 
# Number of reflections with Friedels Law is 0 
# Theoretical number of reflections is about 3369 


_diffrn_reflns_theta_min         2.144
_diffrn_reflns_theta_max         26.050
_diffrn_measured_fraction_theta_max 0.968

_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_full 0.976


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              23
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.73
_refine_diff_density_max         0.91


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>1.3\s(I)
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     0
_refine_ls_number_parameters     208
_oxford_refine_ls_R_factor_ref   0.0853
_refine_ls_wR_factor_ref         0.0720
_refine_ls_goodness_of_fit_ref   0.9735
_refine_ls_shift/su_max          0.0003524
_refine_ls_shift/su_mean         0.0000188


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3266
_refine_ls_R_factor_all          0.1131
_refine_ls_wR_factor_all         0.0784

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1869
_refine_ls_R_factor_gt           0.0811
_refine_ls_wR_factor_gt          0.0693

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 3.18 -0.996 2.41 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
P1 P 0.25085(11) 0.55920(6) 0.97295(14) 0.0313 1.0000 Uani . . . . . .
S1 S 0.08280(12) 0.69907(6) 0.93730(15) 0.0396 1.0000 Uani . . . . . .
C1 C 0.1211(4) 0.6125(2) 0.8931(5) 0.0322 1.0000 Uani . . . . . .
C3 C -0.0365(4) 0.6949(2) 0.7921(5) 0.0291 1.0000 Uani . . . . . .
C5 C -0.1306(4) 0.8031(3) 0.8307(5) 0.0337 1.0000 Uani . . . . . .
C7 C -0.2170(6) 0.9200(3) 0.8794(6) 0.0483 1.0000 Uani . . . . . .
C8 C -0.2524(6) 0.8597(3) 0.6271(6) 0.0462 1.0000 Uani . . . . . .
C9 C 0.3926(4) 0.5998(2) 0.8872(5) 0.0330 1.0000 Uani . . . . . .
C10 C 0.4803(5) 0.5535(3) 0.8244(5) 0.0387 1.0000 Uani . . . . . .
C11 C 0.5895(5) 0.5781(3) 0.7525(6) 0.0420 1.0000 Uani . . . . . .
C12 C 0.6126(5) 0.6489(3) 0.7426(6) 0.0410 1.0000 Uani . . . . . .
C13 C 0.5261(5) 0.6960(3) 0.8043(6) 0.0431 1.0000 Uani . . . . . .
C14 C 0.4163(5) 0.6720(3) 0.8767(6) 0.0422 1.0000 Uani . . . . . .
C15 C 0.2549(4) 0.5891(2) 1.1715(5) 0.0327 1.0000 Uani . . . . . .
C16 C 0.1489(5) 0.5715(3) 1.2618(6) 0.0405 1.0000 Uani . . . . . .
C17 C 0.1488(5) 0.5872(3) 1.4168(6) 0.0472 1.0000 Uani . . . . . .
C18 C 0.2533(6) 0.6185(3) 1.4872(6) 0.0465 1.0000 Uani . . . . . .
C19 C 0.3592(5) 0.6360(3) 1.4013(6) 0.0472 1.0000 Uani . . . . . .
C20 C 0.3593(5) 0.6223(3) 1.2448(6) 0.0390 1.0000 Uani . . . . . .
N1 N -0.0423(4) 0.6336(2) 0.7239(5) 0.0386 1.0000 Uani . . . . . .
N2 N 0.0478(4) 0.5864(2) 0.7834(5) 0.0351 1.0000 Uani . . . . . .
N4 N -0.1158(4) 0.7482(2) 0.7442(4) 0.0340 1.0000 Uani . . . . . .
N6 N -0.1993(4) 0.8580(2) 0.7831(5) 0.0370 1.0000 Uani . . . . . .
H51 H -0.0925 0.8048 0.9302 0.0406 1.0000 Uiso R . . . . .
H73 H -0.1824 0.9605 0.8275 0.0716 1.0000 Uiso R . . . . .
H72 H -0.3074 0.9272 0.8963 0.0719 1.0000 Uiso R . . . . .
H71 H -0.1729 0.9139 0.9783 0.0717 1.0000 Uiso R . . . . .
H81 H -0.3406 0.8752 0.6304 0.0695 1.0000 Uiso R . . . . .
H82 H -0.2494 0.8144 0.5785 0.0695 1.0000 Uiso R . . . . .
H83 H -0.2051 0.8933 0.5674 0.0688 1.0000 Uiso R . . . . .
H101 H 0.4646 0.5042 0.8306 0.0475 1.0000 Uiso R . . . . .
H111 H 0.6471 0.5463 0.7112 0.0510 1.0000 Uiso R . . . . .
H121 H 0.6861 0.6662 0.6948 0.0501 1.0000 Uiso R . . . . .
H131 H 0.5414 0.7439 0.7972 0.0533 1.0000 Uiso R . . . . .
H141 H 0.3577 0.7047 0.9182 0.0509 1.0000 Uiso R . . . . .
H161 H 0.0779 0.5487 1.2165 0.0490 1.0000 Uiso R . . . . .
H171 H 0.0763 0.5767 1.4747 0.0571 1.0000 Uiso R . . . . .
H181 H 0.2544 0.6272 1.5940 0.0560 1.0000 Uiso R . . . . .
H191 H 0.4310 0.6577 1.4489 0.0578 1.0000 Uiso R . . . . .
H201 H 0.4303 0.6347 1.1865 0.0472 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 . C1 . 1.811(5) yes
P1 . C9 . 1.837(5) yes
P1 . C15 . 1.812(5) yes
S1 . C1 . 1.736(5) yes
S1 . C3 . 1.747(4) yes
C1 . N2 . 1.303(6) yes
C3 . N1 . 1.306(6) yes
C3 . N4 . 1.364(6) yes
C5 . N4 . 1.296(6) yes
C5 . N6 . 1.324(6) yes
C5 . H51 . 0.941 no
C7 . N6 . 1.459(6) yes
C7 . H73 . 0.965 no
C7 . H72 . 0.963 no
C7 . H71 . 0.970 no
C8 . N6 . 1.449(6) yes
C8 . H81 . 0.964 no
C8 . H82 . 0.959 no
C8 . H83 . 0.964 no
C9 . C10 . 1.388(6) yes
C9 . C14 . 1.396(7) yes
C10 . C11 . 1.390(7) yes
C10 . H101 . 0.951 no
C11 . C12 . 1.369(7) yes
C11 . H111 . 0.928 no
C12 . C13 . 1.386(7) yes
C12 . H121 . 0.937 no
C13 . C14 . 1.394(7) yes
C13 . H131 . 0.925 no
C14 . H141 . 0.947 no
C15 . C16 . 1.408(7) yes
C15 . C20 . 1.395(6) yes
C16 . C17 . 1.377(7) yes
C16 . H161 . 0.934 no
C17 . C18 . 1.368(8) yes
C17 . H171 . 0.937 no
C18 . C19 . 1.385(8) yes
C18 . H181 . 0.941 no
C19 . C20 . 1.382(7) yes
C19 . H191 . 0.940 no
C20 . H201 . 0.935 no
N1 . N2 . 1.387(5) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . P1 . C9 . 102.0(2) yes
C1 . P1 . C15 . 100.8(2) yes
C9 . P1 . C15 . 104.6(2) yes
C1 . S1 . C3 . 87.7(2) yes
P1 . C1 . S1 . 128.2(3) yes
P1 . C1 . N2 . 118.9(3) yes
S1 . C1 . N2 . 112.9(4) yes
S1 . C3 . N1 . 113.0(3) yes
S1 . C3 . N4 . 126.8(3) yes
N1 . C3 . N4 . 120.2(4) yes
N4 . C5 . N6 . 121.6(4) yes
N4 . C5 . H51 . 120.4 no
N6 . C5 . H51 . 118.0 no
N6 . C7 . H73 . 108.8 no
N6 . C7 . H72 . 109.7 no
H73 . C7 . H72 . 109.6 no
N6 . C7 . H71 . 110.2 no
H73 . C7 . H71 . 109.6 no
H72 . C7 . H71 . 109.0 no
N6 . C8 . H81 . 108.7 no
N6 . C8 . H82 . 112.0 no
H81 . C8 . H82 . 109.2 no
N6 . C8 . H83 . 109.2 no
H81 . C8 . H83 . 108.2 no
H82 . C8 . H83 . 109.6 no
P1 . C9 . C10 . 115.7(3) yes
P1 . C9 . C14 . 125.7(4) yes
C10 . C9 . C14 . 118.6(4) yes
C9 . C10 . C11 . 120.9(5) yes
C9 . C10 . H101 . 119.1 no
C11 . C10 . H101 . 120.0 no
C10 . C11 . C12 . 120.3(5) yes
C10 . C11 . H111 . 119.7 no
C12 . C11 . H111 . 120.0 no
C11 . C12 . C13 . 119.6(5) yes
C11 . C12 . H121 . 121.2 no
C13 . C12 . H121 . 119.2 no
C12 . C13 . C14 . 120.6(5) yes
C12 . C13 . H131 . 119.7 no
C14 . C13 . H131 . 119.7 no
C9 . C14 . C13 . 119.9(5) yes
C9 . C14 . H141 . 120.3 no
C13 . C14 . H141 . 119.8 no
P1 . C15 . C16 . 117.0(3) yes
P1 . C15 . C20 . 125.1(4) yes
C16 . C15 . C20 . 117.7(4) yes
C15 . C16 . C17 . 120.7(5) yes
C15 . C16 . H161 . 119.9 no
C17 . C16 . H161 . 119.4 no
C16 . C17 . C18 . 120.6(5) yes
C16 . C17 . H171 . 119.8 no
C18 . C17 . H171 . 119.5 no
C17 . C18 . C19 . 119.8(5) yes
C17 . C18 . H181 . 120.5 no
C19 . C18 . H181 . 119.7 no
C18 . C19 . C20 . 120.2(5) yes
C18 . C19 . H191 . 120.2 no
C20 . C19 . H191 . 119.6 no
C15 . C20 . C19 . 120.9(5) yes
C15 . C20 . H201 . 118.9 no
C19 . C20 . H201 . 120.2 no
C3 . N1 . N2 . 112.6(4) yes
N1 . N2 . C1 . 113.7(4) yes
C3 . N4 . C5 . 120.0(4) yes
C7 . N6 . C8 . 117.8(4) yes
C7 . N6 . C5 . 122.2(4) yes
C8 . N6 . C5 . 119.9(4) yes


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cpd21
_database_code_depnum_ccdc_archive 'CCDC 1467314'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;

_audit_creation_date             2016-04-21T17:31:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H23 N3 O3 P2 S'
_chemical_formula_sum            'C27 H23 N3 O3 P2 S'
_chemical_formula_weight         531.48
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   13.2093(12)
_cell_length_b                   12.8509(12)
_cell_length_c                   19.0029(14)
_cell_angle_alpha                90
_cell_angle_beta                 126.095(5)
_cell_angle_gamma                90
_cell_volume                     2606.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      30.54
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.960

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_number            24526
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             4755
_reflns_number_gt                4225
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       APEX2
_computing_cell_refinement       'APEX2 and SAINT'
_computing_data_reduction        SAINT
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0401P)²+1.5235P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4755
_refine_ls_number_parameters     378
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.032
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.4
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 1.11108(4) 0.44064(3) 0.73190(3) 0.02728(12) Uani 1 1 d . . .
P1 P 0.74248(4) 0.67150(3) 0.74017(3) 0.01951(12) Uani 1 1 d . . .
P2 P 0.98391(4) 0.58297(3) 0.79155(3) 0.01908(11) Uani 1 1 d . . .
O1 O 0.64628(12) 0.72840(10) 0.64891(8) 0.0300(3) Uani 1 1 d . . .
O3 O 0.75020(13) 0.73417(10) 0.80779(8) 0.0317(3) Uani 1 1 d . . .
N3 N 0.86106(13) 0.64902(12) 0.74309(9) 0.0253(3) Uani 1 1 d . . .
N1 N 0.98441(14) 0.53668(11) 0.58353(9) 0.0236(3) Uani 1 1 d . . .
N2 N 1.12520(16) 0.41236(12) 0.59727(10) 0.0308(4) Uani 1 1 d D . .
C13 C 0.64317(16) 0.71016(15) 0.57484(11) 0.0278(4) Uani 1 1 d . . .
C14 C 0.61547(18) 0.61392(17) 0.53646(12) 0.0357(4) Uani 1 1 d . . .
H14 H 0.6035 0.556 0.5618 0.043 Uiso 1 1 calc R . .
C15 C 0.6053(2) 0.6028(2) 0.45963(14) 0.0482(6) Uani 1 1 d . . .
H15 H 0.5863 0.5365 0.4324 0.058 Uiso 1 1 calc R . .
C16 C 0.6223(2) 0.6865(2) 0.42271(14) 0.0545(7) Uani 1 1 d . . .
H16 H 0.6141 0.6782 0.3699 0.065 Uiso 1 1 calc R . .
C17 C 0.6510(2) 0.7819(2) 0.46233(15) 0.0542(7) Uani 1 1 d . . .
H17 H 0.6637 0.8397 0.4371 0.065 Uiso 1 1 calc R . .
C18 C 0.66189(19) 0.79485(18) 0.53911(14) 0.0417(5) Uani 1 1 d . . .
H18 H 0.6819 0.861 0.5666 0.05 Uiso 1 1 calc R . .
O2 O 0.68073(13) 0.56066(10) 0.73136(9) 0.0317(3) Uani 1 1 d D A .
C7 C 0.60360(18) 0.54086(15) 0.75792(13) 0.0324(4) Uani 1 1 d D . .
C8 C 0.4958(9) 0.5893(7) 0.7301(9) 0.0422(15) Uani 0.59 1 d PDU A 1
H8 H 0.4686 0.6468 0.6916 0.051 Uiso 0.59 1 calc PR A 1
C9 C 0.4229(6) 0.5556(5) 0.7577(5) 0.0477(13) Uani 0.59 1 d PDU A 1
H9 H 0.3461 0.5893 0.7369 0.057 Uiso 0.59 1 calc PR A 1
C10 C 0.4630(6) 0.4746(5) 0.8143(4) 0.0511(12) Uani 0.59 1 d PDU A 1
H10 H 0.4123 0.4501 0.8312 0.061 Uiso 0.59 1 calc PR A 1
C11 C 0.5759(5) 0.4281(5) 0.8471(4) 0.0534(13) Uani 0.59 1 d PDU A 1
H11 H 0.6049 0.3742 0.889 0.064 Uiso 0.59 1 calc PR A 1
C12 C 0.6486(6) 0.4588(6) 0.8197(5) 0.0456(14) Uani 0.59 1 d PDU A 1
H12 H 0.7263 0.4259 0.8418 0.055 Uiso 0.59 1 calc PR A 1
C8' C 0.5026(13) 0.6085(12) 0.7245(13) 0.0422(17) Uani 0.41 1 d PDU A 2
H8' H 0.4919 0.6671 0.6903 0.051 Uiso 0.41 1 calc PR A 2
C9' C 0.4180(9) 0.5863(8) 0.7437(7) 0.0484(17) Uani 0.41 1 d PDU A 2
H9' H 0.3497 0.632 0.7244 0.058 Uiso 0.41 1 calc PR A 2
C10' C 0.4327(8) 0.4997(8) 0.7899(6) 0.0521(16) Uani 0.41 1 d PDU A 2
H10' H 0.3734 0.4852 0.8016 0.063 Uiso 0.41 1 calc PR A 2
C11' C 0.5313(8) 0.4322(8) 0.8202(6) 0.0524(15) Uani 0.41 1 d PDU A 2
H11' H 0.5406 0.3719 0.8524 0.063 Uiso 0.41 1 calc PR A 2
C12' C 0.6170(10) 0.4550(10) 0.8022(8) 0.0471(17) Uani 0.41 1 d PDU A 2
H12' H 0.6851 0.4092 0.8215 0.056 Uiso 0.41 1 calc PR A 2
C25 C 0.98632(17) 0.46925(13) 0.84782(11) 0.0237(4) Uani 1 1 d . . .
C26 C 0.90612(19) 0.38772(15) 0.79782(13) 0.0328(4) Uani 1 1 d . . .
H26 H 0.8548 0.3921 0.7361 0.039 Uiso 1 1 calc R . .
C27 C 0.9013(2) 0.30042(16) 0.83818(15) 0.0427(5) Uani 1 1 d . . .
H27 H 0.8469 0.2445 0.8042 0.051 Uiso 1 1 calc R . .
C28 C 0.9759(2) 0.29446(16) 0.92809(16) 0.0455(6) Uani 1 1 d . . .
H28 H 0.9715 0.2347 0.9556 0.055 Uiso 1 1 calc R . .
C29 C 1.0558(2) 0.37383(18) 0.97781(14) 0.0442(6) Uani 1 1 d . . .
H29 H 1.1073 0.3686 1.0395 0.053 Uiso 1 1 calc R . .
C30 C 1.06191(19) 0.46205(16) 0.93818(12) 0.0336(4) Uani 1 1 d . . .
H30 H 1.1174 0.5172 0.9726 0.04 Uiso 1 1 calc R . .
C19 C 1.11615(16) 0.66354(14) 0.86840(11) 0.0244(4) Uani 1 1 d . . .
C20 C 1.10147(18) 0.73850(15) 0.91423(12) 0.0312(4) Uani 1 1 d . . .
H20 H 1.0241 0.7441 0.9069 0.037 Uiso 1 1 calc R . .
C21 C 1.1990(2) 0.80528(16) 0.97059(13) 0.0401(5) Uani 1 1 d . . .
H21 H 1.1887 0.8558 1.0024 0.048 Uiso 1 1 calc R . .
C22 C 1.3102(2) 0.79870(19) 0.98054(15) 0.0474(6) Uani 1 1 d . . .
H22 H 1.3774 0.8439 1.02 0.057 Uiso 1 1 calc R . .
C23 C 1.3248(2) 0.7270(2) 0.93362(17) 0.0588(7) Uani 1 1 d . . .
H23 H 1.4011 0.7242 0.9391 0.071 Uiso 1 1 calc R . .
C24 C 1.2287(2) 0.65888(19) 0.87840(15) 0.0461(6) Uani 1 1 d . . .
H24 H 1.24 0.6084 0.847 0.055 Uiso 1 1 calc R . .
C1 C 1.00531(16) 0.53716(13) 0.71372(10) 0.0214(3) Uani 1 1 d . . .
C2 C 0.94872(16) 0.57655(13) 0.63243(11) 0.0222(4) Uani 1 1 d . . .
H2 H 0.887 0.6296 0.6105 0.027 Uiso 1 1 calc R . .
C3 C 1.07153(16) 0.46434(13) 0.62756(10) 0.0227(4) Uani 1 1 d . . .
H102 H 1.1755(18) 0.3581(13) 0.6261(13) 0.045(6) Uiso 1 1 d D . .
H202 H 1.099(2) 0.4279(18) 0.5424(8) 0.047(7) Uiso 1 1 d D . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C1 1.7439(17) . ?
S1 C3 1.7540(16) . ?
P1 O3 1.4683(13) . ?
P1 N3 1.5613(15) . ?
P1 O1 1.6000(12) . ?
P1 O2 1.6005(13) . ?
P2 N3 1.5624(15) . ?
P2 C1 1.7626(17) . ?
P2 C25 1.8001(17) . ?
P2 C19 1.8028(18) . ?
O1 C13 1.404(2) . ?
N1 C3 1.324(2) . ?
N1 C2 1.365(2) . ?
N2 C3 1.327(2) . ?
N2 H102 0.894(10) . ?
N2 H202 0.905(10) . ?
C13 C14 1.371(3) . ?
C13 C18 1.380(3) . ?
C14 C15 1.392(3) . ?
C14 H14 0.95 . ?
C15 C16 1.373(4) . ?
C15 H15 0.95 . ?
C16 C17 1.371(4) . ?
C16 H16 0.95 . ?
C17 C18 1.390(3) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
O2 C7 1.401(2) . ?
C7 C12' 1.335(10) . ?
C7 C8 1.344(7) . ?
C7 C8' 1.393(10) . ?
C7 C12 1.422(7) . ?
C8 C9 1.409(8) . ?
C8 H8 0.95 . ?
C9 C10 1.359(6) . ?
C9 H9 0.95 . ?
C10 C11 1.369(7) . ?
C10 H10 0.95 . ?
C11 C12 1.392(7) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C8' C9' 1.395(10) . ?
C8' H8' 0.95 . ?
C9' C10' 1.359(9) . ?
C9' H9' 0.95 . ?
C10' C11' 1.376(10) . ?
C10' H10' 0.95 . ?
C11' C12' 1.393(10) . ?
C11' H11' 0.95 . ?
C12' H12' 0.95 . ?
C25 C30 1.391(2) . ?
C25 C26 1.392(3) . ?
C26 C27 1.381(3) . ?
C26 H26 0.95 . ?
C27 C28 1.383(3) . ?
C27 H27 0.95 . ?
C28 C29 1.369(3) . ?
C28 H28 0.95 . ?
C29 C30 1.389(3) . ?
C29 H29 0.95 . ?
C30 H30 0.95 . ?
C19 C24 1.385(3) . ?
C19 C20 1.387(3) . ?
C20 C21 1.385(3) . ?
C20 H20 0.95 . ?
C21 C22 1.369(3) . ?
C21 H21 0.95 . ?
C22 C23 1.372(3) . ?
C22 H22 0.95 . ?
C23 C24 1.381(3) . ?
C23 H23 0.95 . ?
C24 H24 0.95 . ?
C1 C2 1.357(2) . ?
C2 H2 0.95 . ?

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
C1 S1 C3 88.98(8) . . ?
O3 P1 N3 121.29(8) . . ?
O3 P1 O1 107.41(7) . . ?
N3 P1 O1 105.23(7) . . ?
O3 P1 O2 110.36(7) . . ?
N3 P1 O2 106.13(8) . . ?
O1 P1 O2 105.25(8) . . ?
N3 P2 C1 108.13(8) . . ?
N3 P2 C25 116.10(8) . . ?
C1 P2 C25 105.77(8) . . ?
N3 P2 C19 109.86(8) . . ?
C1 P2 C19 108.29(8) . . ?
C25 P2 C19 108.39(8) . . ?
C13 O1 P1 123.09(11) . . ?
P1 N3 P2 142.51(10) . . ?
C3 N1 C2 110.69(14) . . ?
C3 N2 H102 121.4(15) . . ?
C3 N2 H202 116.4(15) . . ?
H102 N2 H202 121(2) . . ?
C14 C13 C18 121.24(18) . . ?
C14 C13 O1 121.66(17) . . ?
C18 C13 O1 116.99(18) . . ?
C13 C14 C15 118.8(2) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.5(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 119.0(2) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C7 O2 P1 123.91(12) . . ?
C12' C7 C8 110.3(6) . . ?
C12' C7 C8' 122.6(8) . . ?
C12' C7 O2 121.5(6) . . ?
C8 C7 O2 126.9(4) . . ?
C8' C7 O2 115.3(6) . . ?
C8 C7 C12 119.9(6) . . ?
C8' C7 C12 131.4(7) . . ?
O2 C7 C12 113.2(4) . . ?
C7 C8 C9 120.6(6) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 119.8(6) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.4(5) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.8(5) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 118.3(6) . . ?
C11 C12 H12 120.8 . . ?
C7 C12 H12 120.8 . . ?
C7 C8' C9' 117.0(9) . . ?
C7 C8' H8' 121.5 . . ?
C9' C8' H8' 121.5 . . ?
C10' C9' C8' 120.3(9) . . ?
C10' C9' H9' 119.8 . . ?
C8' C9' H9' 119.8 . . ?
C9' C10' C11' 121.8(8) . . ?
C9' C10' H10' 119.1 . . ?
C11' C10' H10' 119.1 . . ?
C10' C11' C12' 118.1(8) . . ?
C10' C11' H11' 121 . . ?
C12' C11' H11' 121 . . ?
C7 C12' C11' 120.2(9) . . ?
C7 C12' H12' 119.9 . . ?
C11' C12' H12' 119.9 . . ?
C30 C25 C26 119.81(17) . . ?
C30 C25 P2 122.41(15) . . ?
C26 C25 P2 117.75(13) . . ?
C27 C26 C25 119.85(19) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 119.9(2) . . ?
C26 C27 H27 120 . . ?
C28 C27 H27 120 . . ?
C29 C28 C27 120.65(19) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.11(19) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 119.7(2) . . ?
C29 C30 H30 120.2 . . ?
C25 C30 H30 120.2 . . ?
C24 C19 C20 118.69(17) . . ?
C24 C19 P2 122.40(14) . . ?
C20 C19 P2 118.71(14) . . ?
C21 C20 C19 120.38(18) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.14(19) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.1(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 120.1(2) . . ?
C22 C23 H23 120 . . ?
C24 C23 H23 120 . . ?
C23 C24 C19 120.5(2) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
C2 C1 S1 109.31(12) . . ?
C2 C1 P2 125.28(13) . . ?
S1 C1 P2 125.26(10) . . ?
C1 C2 N1 117.09(15) . . ?
C1 C2 H2 121.5 . . ?
N1 C2 H2 121.5 . . ?
N1 C3 N2 124.53(15) . . ?
N1 C3 S1 113.91(12) . . ?
N2 C3 S1 121.56(13) . . ?


# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cpd28
_database_code_depnum_ccdc_archive 'CCDC 1467315'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   8.0266(7)
_cell_length_b                   11.3613(9)
_cell_length_c                   17.8128(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.910(9)
_cell_angle_gamma                90
_cell_volume                     1620.6(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Au -2.0133 8.8022 16.8819 0.4611 18.5913 8.6216 25.5582 1.4826 5.8600 36.3956
12.0658 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C15 H13 Au1 Cl1 N2 P1 S1 
# Dc =      2.12 Fooo =    976.00 Mu =     94.63 M =    516.74
# Found Formula = C15 H13 Au1 Cl1 N2 P1 S1 
# Dc =      2.12 FOOO =    976.00 Mu =     94.63 M =    516.74

_chemical_formula_sum            'C15 H13 Au1 Cl1 N2 P1 S1'
_chemical_formula_moiety         'C15 H13 Au1 Cl1 N2 P1 S1'
_chemical_compound_source        ?
_chemical_formula_weight         516.74


_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    2.118
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    9.463

# Sheldrick geometric approximatio 0.39 0.39 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.27
_exptl_absorpt_correction_T_max  0.39
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'IPDS (Stoe & Cie, 1996)'
_computing_cell_refinement       'IPDS (Stoe & Cie, 1996)'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            16072
_reflns_number_total             3180
_diffrn_reflns_av_R_equivalents  0.059
# Number of reflections without Friedels Law is 3180 
# Number of reflections with Friedels Law is 0 
# Theoretical number of reflections is about 3212 


_diffrn_reflns_theta_min         2.292
_diffrn_reflns_theta_max         26.076
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        25.554
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -1.34
_refine_diff_density_max         1.00


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     0
_refine_ls_number_parameters     190
_oxford_refine_ls_R_factor_ref   0.0316
_refine_ls_wR_factor_ref         0.0341
_refine_ls_goodness_of_fit_ref   1.0922
_refine_ls_shift/su_max          0.0014409
_refine_ls_shift/su_mean         0.0000255


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3167
_refine_ls_R_factor_all          0.0438
_refine_ls_wR_factor_all         0.0395

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2401
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_gt          0.0359

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 -1.22 4.39 -1.99 0.734 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.9087(8) 0.4738(6) 0.9022(3) 0.0312 1.0000 Uani . . . . . .
N2 N 1.1102(9) 0.3587(7) 0.9682(4) 0.0408 1.0000 Uani . . . . . .
C1 C 0.8999(9) 0.4143(6) 0.7769(4) 0.0258 1.0000 Uani . . . . . .
C2 C 0.8392(10) 0.4850(7) 0.8300(4) 0.0304 1.0000 Uani . . . . . .
C3 C 1.0234(10) 0.3916(7) 0.9056(4) 0.0311 1.0000 Uani . . . . . .
C4 C 0.7492(9) 0.2669(7) 0.6608(4) 0.0281 1.0000 Uani . . . . . .
C5 C 0.6908(10) 0.1978(7) 0.7185(4) 0.0330 1.0000 Uani . . . . . .
C6 C 0.6239(11) 0.0869(8) 0.7021(5) 0.0423 1.0000 Uani . . . . . .
C7 C 0.6115(11) 0.0468(7) 0.6295(5) 0.0411 1.0000 Uani . . . . . .
C8 C 0.6651(11) 0.1145(8) 0.5720(5) 0.0389 1.0000 Uani . . . . . .
C9 C 0.7358(10) 0.2238(7) 0.5871(4) 0.0309 1.0000 Uani . . . . . .
C10 C 1.0351(9) 0.4053(6) 0.6337(4) 0.0257 1.0000 Uani . . . . . .
C11 C 1.1348(10) 0.3050(7) 0.6388(4) 0.0339 1.0000 Uani . . . . . .
C12 C 1.2888(10) 0.3041(8) 0.6084(5) 0.0385 1.0000 Uani . . . . . .
C13 C 1.3427(10) 0.4023(8) 0.5725(4) 0.0370 1.0000 Uani . . . . . .
C14 C 1.2440(10) 0.5009(8) 0.5660(5) 0.0392 1.0000 Uani . . . . . .
C15 C 1.0918(10) 0.5031(7) 0.5975(4) 0.0330 1.0000 Uani . . . . . .
Au1 Au 0.68532(3) 0.56513(3) 0.643240(16) 0.0247 1.0000 Uani . . . . . .
P1 P 0.8406(2) 0.40960(16) 0.67944(10) 0.0242 1.0000 Uani . . . . . .
S1 S 1.0551(3) 0.32488(18) 0.81960(11) 0.0346 1.0000 Uani . . . . . .
Cl1 Cl 0.5395(2) 0.72962(16) 0.60323(12) 0.0347 1.0000 Uani . . . . . .
H21 H 0.7546 0.5456 0.8210 0.0360 1.0000 Uiso R . . . . .
H51 H 0.6965 0.2152 0.7665 0.0401 1.0000 Uiso R . . . . .
H61 H 0.6002 0.0429 0.7398 0.0500 1.0000 Uiso R . . . . .
H71 H 0.5550 -0.0281 0.6161 0.0500 1.0000 Uiso R . . . . .
H81 H 0.6592 0.0872 0.5259 0.0470 1.0000 Uiso R . . . . .
H91 H 0.7792 0.2621 0.5464 0.0371 1.0000 Uiso R . . . . .
H111 H 1.0932 0.2355 0.6626 0.0410 1.0000 Uiso R . . . . .
H121 H 1.3512 0.2366 0.6125 0.0460 1.0000 Uiso R . . . . .
H131 H 1.4400 0.3987 0.5518 0.0451 1.0000 Uiso R . . . . .
H141 H 1.2804 0.5657 0.5380 0.0470 1.0000 Uiso R . . . . .
H151 H 1.0315 0.5677 0.5930 0.0401 1.0000 Uiso R . . . . .
H22 H 1.0925 0.3915 1.0104 0.0491 1.0000 Uiso R . . . . .
H23 H 1.1839 0.3040 0.9664 0.0491 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.371(10) yes
N1 . C3 . 1.310(10) yes
N2 . C3 . 1.327(10) yes
N2 . H22 . 0.860 no
N2 . H23 . 0.860 no
C1 . C2 . 1.357(11) yes
C1 . P1 . 1.769(7) yes
C1 . S1 . 1.742(7) yes
C2 . H21 . 0.973 no
C3 . S1 . 1.743(8) yes
C4 . C5 . 1.399(11) yes
C4 . C9 . 1.399(11) yes
C4 . P1 . 1.801(8) yes
C5 . C6 . 1.392(12) yes
C5 . H51 . 0.876 no
C6 . C7 . 1.369(13) yes
C6 . H61 . 0.868 no
C7 . C8 . 1.374(13) yes
C7 . H71 . 0.985 no
C8 . C9 . 1.384(11) yes
C8 . H81 . 0.876 no
C9 . H91 . 0.933 no
C10 . C11 . 1.391(11) yes
C10 . C15 . 1.378(11) yes
C10 . P1 . 1.810(8) yes
C11 . C12 . 1.383(11) yes
C11 . H111 . 0.965 no
C12 . C13 . 1.370(12) yes
C12 . H121 . 0.916 no
C13 . C14 . 1.372(12) yes
C13 . H131 . 0.887 no
C14 . C15 . 1.379(12) yes
C14 . H141 . 0.948 no
C15 . H151 . 0.880 no
Au1 . P1 . 2.2323(18) yes
Au1 . Cl1 . 2.2927(18) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C3 . 110.5(7) yes
C3 . N2 . H22 . 120.2 no
C3 . N2 . H23 . 119.8 no
H22 . N2 . H23 . 120.0 no
C2 . C1 . P1 . 128.1(6) yes
C2 . C1 . S1 . 108.7(5) yes
P1 . C1 . S1 . 123.2(4) yes
N1 . C2 . C1 . 117.2(7) yes
N1 . C2 . H21 . 117.1 no
C1 . C2 . H21 . 125.7 no
N2 . C3 . N1 . 124.6(7) yes
N2 . C3 . S1 . 121.1(6) yes
N1 . C3 . S1 . 114.4(6) yes
C5 . C4 . C9 . 118.9(7) yes
C5 . C4 . P1 . 121.5(6) yes
C9 . C4 . P1 . 119.5(6) yes
C4 . C5 . C6 . 119.9(8) yes
C4 . C5 . H51 . 126.3 no
C6 . C5 . H51 . 113.8 no
C5 . C6 . C7 . 120.1(8) yes
C5 . C6 . H61 . 117.5 no
C7 . C6 . H61 . 122.2 no
C6 . C7 . C8 . 120.8(8) yes
C6 . C7 . H71 . 121.2 no
C8 . C7 . H71 . 117.7 no
C7 . C8 . C9 . 120.2(8) yes
C7 . C8 . H81 . 120.1 no
C9 . C8 . H81 . 119.7 no
C4 . C9 . C8 . 120.1(8) yes
C4 . C9 . H91 . 123.8 no
C8 . C9 . H91 . 115.9 no
C11 . C10 . C15 . 119.0(7) yes
C11 . C10 . P1 . 120.2(6) yes
C15 . C10 . P1 . 120.7(6) yes
C10 . C11 . C12 . 120.4(8) yes
C10 . C11 . H111 . 118.9 no
C12 . C11 . H111 . 120.7 no
C11 . C12 . C13 . 119.7(8) yes
C11 . C12 . H121 . 118.2 no
C13 . C12 . H121 . 122.1 no
C12 . C13 . C14 . 120.3(8) yes
C12 . C13 . H131 . 118.1 no
C14 . C13 . H131 . 121.5 no
C13 . C14 . C15 . 120.2(8) yes
C13 . C14 . H141 . 118.8 no
C15 . C14 . H141 . 120.9 no
C14 . C15 . C10 . 120.4(8) yes
C14 . C15 . H151 . 118.3 no
C10 . C15 . H151 . 121.3 no
P1 . Au1 . Cl1 . 176.62(7) yes
C10 . P1 . C4 . 104.2(3) yes
C10 . P1 . C1 . 105.1(3) yes
C4 . P1 . C1 . 106.7(3) yes
C10 . P1 . Au1 . 111.9(2) yes
C4 . P1 . Au1 . 116.5(2) yes
C1 . P1 . Au1 . 111.5(2) yes
C3 . S1 . C1 . 89.3(4) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N2 . H22 . N1 2_767 159.5(3) 0.860 2.184 3.005(11) yes


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cpd29
_database_code_depnum_ccdc_archive 'CCDC 1467316'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          SQUEEZE
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   11.2861(10)
_cell_length_b                   13.7824(13)
_cell_length_c                   20.175(2)
_cell_angle_alpha                82.053(12)
_cell_angle_beta                 82.884(12)
_cell_angle_gamma                88.274(11)
_cell_volume                     3083.9(3)

_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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
Au -2.0133 8.8022 16.8819 0.4611 18.5913 8.6216 25.5582 1.4826 5.8600 36.3956
12.0658 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C27 H27 Au Cl N18 P3 S9'
_chemical_formula_moiety         'C27 H27 Au N18 P3 S9, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         1217.57


_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_max          0.450

_exptl_crystal_density_diffrn    1.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    2.845

# Sheldrick geometric approximatio 0.49 0.49 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_T_max  0.49
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'IPDS (Stoe & Cie, 1996)'
_computing_cell_refinement       'IPDS (Stoe & Cie, 1996)'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      180
_diffrn_reflns_number            11269
_reflns_number_total             11269
_diffrn_reflns_av_R_equivalents  0.066
# Number of reflections without Friedels Law is 11269 
# Number of reflections with Friedels Law is 0 
# Theoretical number of reflections is about 12143 


_diffrn_reflns_theta_min         2.053
_diffrn_reflns_theta_max         26.014
_diffrn_measured_fraction_theta_max 0.930

_diffrn_reflns_theta_full        25.233
_diffrn_measured_fraction_theta_full 0.938


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              -15
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.88
_refine_diff_density_max         1.17


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         8895
_refine_ls_number_restraints     0
_refine_ls_number_parameters     532
_oxford_refine_ls_R_factor_ref   0.0305
_refine_ls_wR_factor_ref         0.0344
_refine_ls_goodness_of_fit_ref   1.1144
_refine_ls_shift/su_max          0.0008505
_refine_ls_shift/su_mean         0.0000378


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        11222
_refine_ls_R_factor_all          0.0372
_refine_ls_wR_factor_all         0.0356

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                9374
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_gt          0.0349

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 4.34 -1.29 3.96 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Au1 Au 0.351109(10) 0.247177(9) 0.718956(6) 0.0233 1.0000 Uani . . . . . .
P1 P 0.35371(7) 0.15623(6) 0.62945(4) 0.0228 1.0000 Uani . . . . . .
P2 P 0.40799(7) 0.20447(6) 0.82783(4) 0.0239 1.0000 Uani . . . . . .
P3 P 0.32967(7) 0.42402(6) 0.69790(4) 0.0242 1.0000 Uani . . . . . .
S1 S 0.61664(7) 0.09468(7) 0.60377(4) 0.0368 1.0000 Uani . . . . . .
S2 S 0.34732(8) -0.05579(6) 0.59405(4) 0.0309 1.0000 Uani . . . . . .
S3 S 0.23018(8) 0.14922(7) 0.49949(4) 0.0353 1.0000 Uani . . . . . .
S4 S 0.56221(9) 0.03022(8) 0.78319(5) 0.0399 1.0000 Uani . . . . . .
S5 S 0.32647(7) 0.07242(7) 0.96223(4) 0.0344 1.0000 Uani . . . . . .
S6 S 0.55110(8) 0.38968(7) 0.83363(4) 0.0331 1.0000 Uani . . . . . .
S7 S 0.52964(9) 0.58374(7) 0.67021(5) 0.0419 1.0000 Uani . . . . . .
S8 S 0.29079(7) 0.50492(7) 0.55131(4) 0.0298 1.0000 Uani . . . . . .
S9 S 0.29523(9) 0.58532(7) 0.79477(4) 0.0371 1.0000 Uani . . . . . .
C1 C 0.4960(3) 0.1658(2) 0.57893(16) 0.0254 1.0000 Uani . . . . . .
C2 C 0.5341(3) 0.2300(3) 0.52408(17) 0.0319 1.0000 Uani . . . . . .
C3 C 0.7069(3) 0.1579(3) 0.53684(17) 0.0320 1.0000 Uani . . . . . .
C4 C 0.3345(3) 0.0280(2) 0.65190(15) 0.0255 1.0000 Uani . . . . . .
C5 C 0.3002(3) -0.0209(3) 0.71350(17) 0.0346 1.0000 Uani . . . . . .
C6 C 0.2989(3) -0.1474(3) 0.65902(18) 0.0332 1.0000 Uani . . . . . .
C7 C 0.2490(3) 0.1980(2) 0.57237(16) 0.0267 1.0000 Uani . . . . . .
C8 C 0.1658(3) 0.2696(3) 0.58101(17) 0.0292 1.0000 Uani . . . . . .
C9 C 0.1116(3) 0.2298(2) 0.48834(16) 0.0258 1.0000 Uani . . . . . .
C10 C 0.5390(3) 0.1275(3) 0.82974(15) 0.0276 1.0000 Uani . . . . . .
C11 C 0.6221(4) 0.1242(3) 0.87212(19) 0.0406 1.0000 Uani . . . . . .
C12 C 0.6836(4) -0.0063(4) 0.8263(2) 0.0547 1.0000 Uani . . . . . .
C13 C 0.2982(3) 0.1359(3) 0.88489(16) 0.0272 1.0000 Uani . . . . . .
C14 C 0.1864(3) 0.1179(3) 0.87459(18) 0.0372 1.0000 Uani . . . . . .
C15 C 0.1825(3) 0.0270(3) 0.97368(19) 0.0382 1.0000 Uani . . . . . .
C16 C 0.4481(3) 0.3008(3) 0.87129(15) 0.0275 1.0000 Uani . . . . . .
C17 C 0.4045(3) 0.3223(3) 0.93347(18) 0.0370 1.0000 Uani . . . . . .
C18 C 0.5268(3) 0.4479(3) 0.90586(18) 0.0355 1.0000 Uani . . . . . .
C19 C 0.4786(3) 0.4658(3) 0.67134(16) 0.0280 1.0000 Uani . . . . . .
C20 C 0.5689(3) 0.4102(3) 0.64643(16) 0.0297 1.0000 Uani . . . . . .
C21 C 0.6702(4) 0.5457(3) 0.63655(19) 0.0404 1.0000 Uani . . . . . .
C22 C 0.2435(3) 0.4922(3) 0.63751(16) 0.0285 1.0000 Uani . . . . . .
C23 C 0.1328(3) 0.5315(3) 0.64738(17) 0.0342 1.0000 Uani . . . . . .
C24 C 0.1540(3) 0.5622(3) 0.53708(17) 0.0307 1.0000 Uani . . . . . .
C25 C 0.2733(3) 0.4693(2) 0.77432(16) 0.0258 1.0000 Uani . . . . . .
C26 C 0.1991(3) 0.4205(3) 0.82391(18) 0.0343 1.0000 Uani . . . . . .
C27 C 0.1997(4) 0.5549(3) 0.86963(19) 0.0406 1.0000 Uani . . . . . .
N1 N 0.6533(3) 0.2261(2) 0.49969(15) 0.0343 1.0000 Uani . . . . . .
N2 N 0.8244(3) 0.1337(3) 0.52679(19) 0.0472 1.0000 Uani . . . . . .
N3 N 0.2808(3) -0.1187(2) 0.71904(15) 0.0401 1.0000 Uani . . . . . .
N4 N 0.2824(3) -0.2387(2) 0.64661(17) 0.0448 1.0000 Uani . . . . . .
N5 N 0.0888(2) 0.2882(2) 0.53400(14) 0.0294 1.0000 Uani . . . . . .
N6 N 0.0456(3) 0.2309(2) 0.43588(15) 0.0323 1.0000 Uani . . . . . .
N7 N 0.7057(4) 0.0515(3) 0.8700(2) 0.0574 1.0000 Uani . . . . . .
N8 N 0.7484(6) -0.0857(4) 0.8149(3) 0.0939 1.0000 Uani . . . . . .
N9 N 0.1192(3) 0.0573(3) 0.92364(17) 0.0459 1.0000 Uani . . . . . .
N10 N 0.1433(3) -0.0347(3) 1.02782(18) 0.0512 1.0000 Uani . . . . . .
N11 N 0.4485(3) 0.4038(3) 0.95306(16) 0.0436 1.0000 Uani . . . . . .
N12 N 0.5850(3) 0.5283(3) 0.91105(17) 0.0472 1.0000 Uani . . . . . .
N13 N 0.6773(3) 0.4537(3) 0.62658(17) 0.0402 1.0000 Uani . . . . . .
N14 N 0.7625(4) 0.6065(3) 0.6223(2) 0.0695 1.0000 Uani . . . . . .
N15 N 0.0812(3) 0.5718(3) 0.59232(15) 0.0396 1.0000 Uani . . . . . .
N16 N 0.1292(3) 0.5924(3) 0.47485(15) 0.0389 1.0000 Uani . . . . . .
N17 N 0.1574(3) 0.4670(3) 0.87791(17) 0.0445 1.0000 Uani . . . . . .
N18 N 0.1784(4) 0.6184(3) 0.9142(2) 0.0653 1.0000 Uani . . . . . .
Cl1 Cl 0.3062(2) 0.19668(12) 0.30872(7) 0.0956 1.0000 Uani . . . . . .
H21 H 0.4826 0.2750 0.5037 0.0394 1.0000 Uiso R . . . . .
H51 H 0.2887 0.0115 0.7508 0.0403 1.0000 Uiso R . . . . .
H81 H 0.1598 0.3030 0.6181 0.0355 1.0000 Uiso R . . . . .
H111 H 0.6220 0.1708 0.9020 0.0503 1.0000 Uiso R . . . . .
H141 H 0.1556 0.1443 0.8355 0.0443 1.0000 Uiso R . . . . .
H171 H 0.3457 0.2839 0.9609 0.0443 1.0000 Uiso R . . . . .
H201 H 0.5588 0.3442 0.6424 0.0373 1.0000 Uiso R . . . . .
H231 H 0.0924 0.5303 0.6907 0.0412 1.0000 Uiso R . . . . .
H261 H 0.1769 0.3554 0.8227 0.0421 1.0000 Uiso R . . . . .
H61 H 0.0024 0.2809 0.4251 0.0386 1.0000 Uiso R . . . . .
H62 H 0.0672 0.1958 0.4040 0.0386 1.0000 Uiso R . . . . .
H161 H 0.0623 0.6213 0.4694 0.0477 1.0000 Uiso R . . . . .
H162 H 0.1814 0.5868 0.4407 0.0477 1.0000 Uiso R . . . . .
H22 H 0.8514 0.0828 0.5496 0.0568 1.0000 Uiso R . . . . .
H23 H 0.8696 0.1665 0.4947 0.0568 1.0000 Uiso R . . . . .
H41 H 0.2637 -0.2838 0.6801 0.0532 1.0000 Uiso R . . . . .
H42 H 0.2961 -0.2519 0.6058 0.0532 1.0000 Uiso R . . . . .
H82 H 0.8179 -0.0925 0.8271 0.1113 1.0000 Uiso R . . . . .
H83 H 0.7244 -0.1254 0.7906 0.1113 1.0000 Uiso R . . . . .
H101 H 0.1832 -0.0442 1.0621 0.0601 1.0000 Uiso R . . . . .
H102 H 0.0689 -0.0494 1.0352 0.0601 1.0000 Uiso R . . . . .
H142 H 0.7535 0.6661 0.6313 0.0802 1.0000 Uiso R . . . . .
H143 H 0.8308 0.5863 0.6050 0.0802 1.0000 Uiso R . . . . .
H121 H 0.5794 0.5501 0.9489 0.0569 1.0000 Uiso R . . . . .
H122 H 0.6358 0.5533 0.8778 0.0569 1.0000 Uiso R . . . . .
H181 H 0.1350 0.6023 0.9519 0.0787 1.0000 Uiso R . . . . .
H182 H 0.1979 0.6791 0.9019 0.0787 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Au1 . P1 . 2.3332(8) yes
Au1 . P2 . 2.3564(8) yes
Au1 . P3 . 2.4256(9) yes
P1 . C1 . 1.790(3) yes
P1 . C4 . 1.776(3) yes
P1 . C7 . 1.780(3) yes
P2 . C10 . 1.795(4) yes
P2 . C13 . 1.781(3) yes
P2 . C16 . 1.787(3) yes
P3 . C19 . 1.787(3) yes
P3 . C22 . 1.799(3) yes
P3 . C25 . 1.780(3) yes
S1 . C1 . 1.737(3) yes
S1 . C3 . 1.734(4) yes
S2 . C4 . 1.743(3) yes
S2 . C6 . 1.737(4) yes
S3 . C7 . 1.737(3) yes
S3 . C9 . 1.729(3) yes
S4 . C10 . 1.736(3) yes
S4 . C12 . 1.738(4) yes
S5 . C13 . 1.741(3) yes
S5 . C15 . 1.736(4) yes
S6 . C16 . 1.743(3) yes
S6 . C18 . 1.747(3) yes
S7 . C19 . 1.737(3) yes
S7 . C21 . 1.742(4) yes
S8 . C22 . 1.741(3) yes
S8 . C24 . 1.750(3) yes
S9 . C25 . 1.738(3) yes
S9 . C27 . 1.752(4) yes
C1 . C2 . 1.351(5) yes
C2 . N1 . 1.376(5) yes
C2 . H21 . 0.926 no
C3 . N1 . 1.302(5) yes
C3 . N2 . 1.355(5) yes
C4 . C5 . 1.346(5) yes
C5 . N3 . 1.360(5) yes
C5 . H51 . 0.921 no
C6 . N3 . 1.315(5) yes
C6 . N4 . 1.339(5) yes
C7 . C8 . 1.355(5) yes
C8 . N5 . 1.359(4) yes
C8 . H81 . 0.927 no
C9 . N5 . 1.303(4) yes
C9 . N6 . 1.366(4) yes
C10 . C11 . 1.340(5) yes
C11 . N7 . 1.357(5) yes
C11 . H111 . 0.939 no
C12 . N7 . 1.316(6) yes
C12 . N8 . 1.328(6) yes
C13 . C14 . 1.339(5) yes
C14 . N9 . 1.370(5) yes
C14 . H141 . 0.925 no
C15 . N9 . 1.322(5) yes
C15 . N10 . 1.326(5) yes
C16 . C17 . 1.358(5) yes
C17 . N11 . 1.368(5) yes
C17 . H171 . 0.936 no
C18 . N11 . 1.312(5) yes
C18 . N12 . 1.328(5) yes
C19 . C20 . 1.346(5) yes
C20 . N13 . 1.368(4) yes
C20 . H201 . 0.936 no
C21 . N13 . 1.310(5) yes
C21 . N14 . 1.335(5) yes
C22 . C23 . 1.349(5) yes
C23 . N15 . 1.361(5) yes
C23 . H231 . 0.933 no
C24 . N15 . 1.320(4) yes
C24 . N16 . 1.328(5) yes
C25 . C26 . 1.340(5) yes
C26 . N17 . 1.367(5) yes
C26 . H261 . 0.943 no
C27 . N17 . 1.297(5) yes
C27 . N18 . 1.336(5) yes
N2 . H22 . 0.854 no
N2 . H23 . 0.857 no
N4 . H41 . 0.863 no
N4 . H42 . 0.861 no
N6 . H61 . 0.850 no
N6 . H62 . 0.864 no
N8 . H82 . 0.849 no
N8 . H83 . 0.855 no
N10 . H101 . 0.865 no
N10 . H102 . 0.860 no
N12 . H121 . 0.852 no
N12 . H122 . 0.865 no
N14 . H142 . 0.866 no
N14 . H143 . 0.861 no
N16 . H161 . 0.856 no
N16 . H162 . 0.860 no
N18 . H181 . 0.857 no
N18 . H182 . 0.866 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
P1 . Au1 . P2 . 130.96(3) yes
P1 . Au1 . P3 . 119.26(3) yes
P2 . Au1 . P3 . 108.32(3) yes
Au1 . P1 . C1 . 110.20(10) yes
Au1 . P1 . C4 . 115.91(10) yes
C1 . P1 . C4 . 103.73(15) yes
Au1 . P1 . C7 . 113.94(11) yes
C1 . P1 . C7 . 104.68(15) yes
C4 . P1 . C7 . 107.32(15) yes
Au1 . P2 . C10 . 113.57(10) yes
Au1 . P2 . C13 . 113.40(10) yes
C10 . P2 . C13 . 103.70(16) yes
Au1 . P2 . C16 . 118.01(11) yes
C10 . P2 . C16 . 101.14(15) yes
C13 . P2 . C16 . 105.36(15) yes
Au1 . P3 . C19 . 104.12(12) yes
Au1 . P3 . C22 . 126.39(12) yes
C19 . P3 . C22 . 103.76(16) yes
Au1 . P3 . C25 . 109.44(11) yes
C19 . P3 . C25 . 109.77(15) yes
C22 . P3 . C25 . 102.71(15) yes
C1 . S1 . C3 . 88.86(17) yes
C4 . S2 . C6 . 89.22(16) yes
C7 . S3 . C9 . 88.73(15) yes
C10 . S4 . C12 . 88.65(19) yes
C13 . S5 . C15 . 89.18(16) yes
C16 . S6 . C18 . 89.49(16) yes
C19 . S7 . C21 . 88.89(17) yes
C22 . S8 . C24 . 88.79(15) yes
C25 . S9 . C27 . 88.71(17) yes
P1 . C1 . S1 . 120.52(19) yes
P1 . C1 . C2 . 130.1(3) yes
S1 . C1 . C2 . 108.9(2) yes
C1 . C2 . N1 . 117.1(3) yes
C1 . C2 . H21 . 121.8 no
N1 . C2 . H21 . 121.0 no
S1 . C3 . N1 . 115.4(3) yes
S1 . C3 . N2 . 119.3(3) yes
N1 . C3 . N2 . 125.3(3) yes
P1 . C4 . S2 . 124.05(18) yes
P1 . C4 . C5 . 127.7(3) yes
S2 . C4 . C5 . 108.1(3) yes
C4 . C5 . N3 . 118.4(3) yes
C4 . C5 . H51 . 120.7 no
N3 . C5 . H51 . 120.9 no
S2 . C6 . N3 . 114.5(3) yes
S2 . C6 . N4 . 120.8(3) yes
N3 . C6 . N4 . 124.7(3) yes
P1 . C7 . S3 . 125.91(19) yes
P1 . C7 . C8 . 125.2(3) yes
S3 . C7 . C8 . 108.8(2) yes
C7 . C8 . N5 . 117.1(3) yes
C7 . C8 . H81 . 121.7 no
N5 . C8 . H81 . 121.1 no
S3 . C9 . N5 . 115.3(2) yes
S3 . C9 . N6 . 122.2(3) yes
N5 . C9 . N6 . 122.5(3) yes
P2 . C10 . S4 . 122.29(18) yes
P2 . C10 . C11 . 127.7(3) yes
S4 . C10 . C11 . 109.3(3) yes
C10 . C11 . N7 . 117.5(4) yes
C10 . C11 . H111 . 120.8 no
N7 . C11 . H111 . 121.7 no
S4 . C12 . N7 . 114.5(3) yes
S4 . C12 . N8 . 122.0(4) yes
N7 . C12 . N8 . 123.6(4) yes
P2 . C13 . S5 . 123.54(18) yes
P2 . C13 . C14 . 127.2(3) yes
S5 . C13 . C14 . 109.0(2) yes
C13 . C14 . N9 . 117.6(3) yes
C13 . C14 . H141 . 121.7 no
N9 . C14 . H141 . 120.7 no
S5 . C15 . N9 . 114.3(3) yes
S5 . C15 . N10 . 121.4(3) yes
N9 . C15 . N10 . 124.3(3) yes
P2 . C16 . S6 . 121.82(18) yes
P2 . C16 . C17 . 129.3(3) yes
S6 . C16 . C17 . 108.8(3) yes
C16 . C17 . N11 . 116.8(3) yes
C16 . C17 . H171 . 121.3 no
N11 . C17 . H171 . 122.0 no
S6 . C18 . N11 . 113.6(3) yes
S6 . C18 . N12 . 121.7(3) yes
N11 . C18 . N12 . 124.7(3) yes
P3 . C19 . S7 . 126.4(2) yes
P3 . C19 . C20 . 124.5(3) yes
S7 . C19 . C20 . 109.0(2) yes
C19 . C20 . N13 . 117.6(3) yes
C19 . C20 . H201 . 121.9 no
N13 . C20 . H201 . 120.5 no
S7 . C21 . N13 . 114.7(3) yes
S7 . C21 . N14 . 121.9(3) yes
N13 . C21 . N14 . 123.4(4) yes
P3 . C22 . S8 . 121.76(19) yes
P3 . C22 . C23 . 129.0(3) yes
S8 . C22 . C23 . 108.8(2) yes
C22 . C23 . N15 . 118.2(3) yes
C22 . C23 . H231 . 120.9 no
N15 . C23 . H231 . 120.9 no
S8 . C24 . N15 . 114.6(3) yes
S8 . C24 . N16 . 120.8(3) yes
N15 . C24 . N16 . 124.6(3) yes
P3 . C25 . S9 . 126.5(2) yes
P3 . C25 . C26 . 124.7(3) yes
S9 . C25 . C26 . 108.6(2) yes
C25 . C26 . N17 . 118.1(3) yes
C25 . C26 . H261 . 121.8 no
N17 . C26 . H261 . 120.1 no
S9 . C27 . N17 . 114.6(3) yes
S9 . C27 . N18 . 120.6(3) yes
N17 . C27 . N18 . 124.8(4) yes
C2 . N1 . C3 . 109.7(3) yes
C3 . N2 . H22 . 120.1 no
C3 . N2 . H23 . 119.3 no
H22 . N2 . H23 . 120.3 no
C5 . N3 . C6 . 109.7(3) yes
C6 . N4 . H41 . 118.9 no
C6 . N4 . H42 . 119.3 no
H41 . N4 . H42 . 121.6 no
C8 . N5 . C9 . 110.1(3) yes
C9 . N6 . H61 . 119.4 no
C9 . N6 . H62 . 120.5 no
H61 . N6 . H62 . 115.4 no
C11 . N7 . C12 . 110.0(3) yes
C12 . N8 . H82 . 119.7 no
C12 . N8 . H83 . 119.8 no
H82 . N8 . H83 . 119.9 no
C14 . N9 . C15 . 109.9(3) yes
C15 . N10 . H101 . 120.4 no
C15 . N10 . H102 . 119.4 no
H101 . N10 . H102 . 116.7 no
C17 . N11 . C18 . 111.4(3) yes
C18 . N12 . H121 . 119.5 no
C18 . N12 . H122 . 119.6 no
H121 . N12 . H122 . 120.3 no
C20 . N13 . C21 . 109.8(3) yes
C21 . N14 . H142 . 119.5 no
C21 . N14 . H143 . 120.3 no
H142 . N14 . H143 . 120.3 no
C23 . N15 . C24 . 109.6(3) yes
C24 . N16 . H161 . 118.9 no
C24 . N16 . H162 . 120.7 no
H161 . N16 . H162 . 120.3 no
C26 . N17 . C27 . 109.9(3) yes
C27 . N18 . H181 . 120.7 no
C27 . N18 . H182 . 119.0 no
H181 . N18 . H182 . 119.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N6 . H61 . N15 2_566 167.23(11) 0.850 2.215 3.050(5) yes
N16 . H161 . N5 2_566 169.02(12) 0.856 2.084 2.929(5) yes
N16 . H162 . N13 2_666 166.44(14) 0.860 2.077 2.920(5) yes
N2 . H23 . N6 1_655 157.54(12) 0.857 2.318 3.128(5) yes
N4 . H42 . N1 2_656 157.66(12) 0.861 2.118 2.933(5) yes
N10 . H101 . N7 2_657 170.14(18) 0.865 1.960 2.816(5) yes
N10 . H102 . N9 2_557 162.84(15) 0.860 2.181 3.013(5) yes
N12 . H121 . N11 2_667 174.72(13) 0.852 2.145 2.994(5) yes

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.002 0.043 0.000 1108 232 ' '
_platon_squeeze_details          
;
;


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cpd23
_database_code_depnum_ccdc_archive 'CCDC 1467317'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;
_audit_creation_date             2016-04-21T17:31:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H22 N4 O3 P2 S'
_chemical_formula_sum            'C26 H22 N4 O3 P2 S'
_chemical_formula_weight         532.48
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1492(3)
_cell_length_b                   11.6047(4)
_cell_length_c                   13.4675(5)
_cell_angle_alpha                65.9950(10)
_cell_angle_beta                 80.8110(10)
_cell_angle_gamma                73.7530(10)
_cell_volume                     1252.34(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8989
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      32.36
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.125
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.993

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_number            15257
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             4538
_reflns_number_gt                4009
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       APEX2
_computing_cell_refinement       'APEX2 and SAINT'
_computing_data_reduction        SAINT
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0432P)²+0.5504P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4538
_refine_ls_number_parameters     333
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.083
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.85188(18) -0.12636(15) 0.31418(13) 0.0187(3) Uani 1 1 d . . .
C3 C 0.98069(18) -0.30114(15) 0.46450(13) 0.0199(3) Uani 1 1 d . . .
C16 C 0.8773(2) 0.38262(16) 0.05926(14) 0.0245(4) Uani 1 1 d . . .
C17 C 1.0054(2) 0.34163(19) 0.00238(16) 0.0317(4) Uani 1 1 d . . .
H17 H 1.0974 0.2929 0.0381 0.038 Uiso 1 1 calc R . .
C18 C 0.9988(2) 0.3723(2) -0.10821(16) 0.0386(5) Uani 1 1 d . . .
H18 H 1.0868 0.3443 -0.1483 0.046 Uiso 1 1 calc R . .
C19 C 0.8655(3) 0.4429(2) -0.15966(16) 0.0429(5) Uani 1 1 d . . .
H19 H 0.8609 0.4633 -0.2351 0.051 Uiso 1 1 calc R . .
C20 C 0.7380(3) 0.4844(2) -0.10119(17) 0.0454(5) Uani 1 1 d . . .
H20 H 0.646 0.5335 -0.1369 0.055 Uiso 1 1 calc R . .
C21 C 0.7429(2) 0.45503(19) 0.00904(16) 0.0352(4) Uani 1 1 d . . .
H21 H 0.6556 0.4842 0.049 0.042 Uiso 1 1 calc R . .
C4 C 0.55095(18) 0.03999(16) 0.27918(13) 0.0211(3) Uani 1 1 d . . .
C5 C 0.5061(2) -0.05588(19) 0.37228(15) 0.0306(4) Uani 1 1 d . . .
H5 H 0.5796 -0.1317 0.4105 0.037 Uiso 1 1 calc R . .
C6 C 0.3542(2) -0.0410(2) 0.40952(16) 0.0391(5) Uani 1 1 d . . .
H6 H 0.3236 -0.107 0.4727 0.047 Uiso 1 1 calc R . .
C7 C 0.2476(2) 0.0697(2) 0.35481(16) 0.0349(5) Uani 1 1 d . . .
H7 H 0.1437 0.0796 0.3805 0.042 Uiso 1 1 calc R . .
C8 C 0.2910(2) 0.1664(2) 0.26271(16) 0.0321(4) Uani 1 1 d . . .
H8 H 0.2172 0.2429 0.2259 0.039 Uiso 1 1 calc R . .
C9 C 0.44199(19) 0.15162(17) 0.22418(15) 0.0252(4) Uani 1 1 d . . .
H9 H 0.4715 0.2174 0.1603 0.03 Uiso 1 1 calc R . .
C10 C 0.74965(18) 0.02248(16) 0.09362(13) 0.0207(3) Uani 1 1 d . . .
C11 C 0.6884(2) -0.06704(19) 0.08043(15) 0.0314(4) Uani 1 1 d . . .
H11 H 0.647 -0.1282 0.1417 0.038 Uiso 1 1 calc R . .
C12 C 0.6882(2) -0.0666(2) -0.02261(17) 0.0388(5) Uani 1 1 d . . .
H12 H 0.6476 -0.1283 -0.0318 0.047 Uiso 1 1 calc R . .
C13 C 0.7464(3) 0.0228(2) -0.11166(16) 0.0424(5) Uani 1 1 d . . .
H13 H 0.7443 0.0236 -0.1822 0.051 Uiso 1 1 calc R . .
C14 C 0.8074(3) 0.1109(2) -0.09869(17) 0.0548(7) Uani 1 1 d . . .
H14 H 0.8487 0.1718 -0.1603 0.066 Uiso 1 1 calc R . .
C15 C 0.8092(3) 0.1114(2) 0.00395(16) 0.0418(5) Uani 1 1 d . . .
H15 H 0.8512 0.1728 0.0126 0.05 Uiso 1 1 calc R . .
C22 C 0.56009(19) 0.41157(16) 0.30156(13) 0.0228(4) Uani 1 1 d . . .
C27 C 0.6184(2) 0.51763(18) 0.27967(16) 0.0323(4) Uani 1 1 d . . .
H27 H 0.7112 0.5264 0.2374 0.039 Uiso 1 1 calc R . .
C26 C 0.5389(2) 0.61130(19) 0.32061(17) 0.0392(5) Uani 1 1 d . . .
H26 H 0.5782 0.6844 0.3067 0.047 Uiso 1 1 calc R . .
C25 C 0.4042(2) 0.5992(2) 0.38103(18) 0.0412(5) Uani 1 1 d . . .
H25 H 0.3498 0.6643 0.4078 0.049 Uiso 1 1 calc R . .
C24 C 0.3480(2) 0.4921(2) 0.40280(17) 0.0406(5) Uani 1 1 d . . .
H24 H 0.2549 0.4837 0.4448 0.049 Uiso 1 1 calc R . .
C23 C 0.4266(2) 0.39649(19) 0.36366(15) 0.0308(4) Uani 1 1 d . . .
H23 H 0.3889 0.3221 0.3795 0.037 Uiso 1 1 calc R . .
N1 N 0.92192(16) -0.34115(13) 0.40332(11) 0.0223(3) Uani 1 1 d . . .
N2 N 1.05280(18) -0.38078(14) 0.55467(12) 0.0270(3) Uani 1 1 d D . .
N3 N 0.84656(16) -0.23884(13) 0.31834(11) 0.0220(3) Uani 1 1 d . . .
N4 N 0.82137(16) 0.13607(13) 0.21867(11) 0.0221(3) Uani 1 1 d . . .
O1 O 0.86477(14) 0.21740(12) 0.36664(9) 0.0263(3) Uani 1 1 d . . .
O2 O 0.62762(13) 0.31753(11) 0.25705(10) 0.0244(3) Uani 1 1 d . . .
O3 O 0.88832(13) 0.35110(11) 0.17076(9) 0.0234(3) Uani 1 1 d . . .
P2 P 0.80524(5) 0.24662(4) 0.26156(3) 0.01830(11) Uani 1 1 d . . .
P1 P 0.74591(5) 0.02782(4) 0.22531(3) 0.01706(11) Uani 1 1 d . . .
S1 S 0.95297(5) -0.13295(4) 0.41604(3) 0.02249(12) Uani 1 1 d . . .
H102 H 1.063(2) -0.4670(10) 0.5750(15) 0.029(5) Uiso 1 1 d D . .
H202 H 1.088(2) -0.345(2) 0.5915(17) 0.048(6) Uiso 1 1 d D . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N3 1.298(2) . ?
C1 S1 1.7388(16) . ?
C1 P1 1.7976(16) . ?
C3 N2 1.329(2) . ?
C3 N1 1.333(2) . ?
C3 S1 1.7433(16) . ?
C16 C17 1.373(3) . ?
C16 C21 1.379(3) . ?
C16 O3 1.407(2) . ?
C17 C18 1.391(3) . ?
C17 H17 0.95 . ?
C18 C19 1.374(3) . ?
C18 H18 0.95 . ?
C19 C20 1.383(3) . ?
C19 H19 0.95 . ?
C20 C21 1.387(3) . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?
C4 C5 1.391(2) . ?
C4 C9 1.398(2) . ?
C4 P1 1.8047(16) . ?
C5 C6 1.388(3) . ?
C5 H5 0.95 . ?
C6 C7 1.379(3) . ?
C6 H6 0.95 . ?
C7 C8 1.384(3) . ?
C7 H7 0.95 . ?
C8 C9 1.385(3) . ?
C8 H8 0.95 . ?
C9 H9 0.95 . ?
C10 C15 1.382(3) . ?
C10 C11 1.390(2) . ?
C10 P1 1.7942(16) . ?
C11 C12 1.386(3) . ?
C11 H11 0.95 . ?
C12 C13 1.375(3) . ?
C12 H12 0.95 . ?
C13 C14 1.372(3) . ?
C13 H13 0.95 . ?
C14 C15 1.387(3) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C22 C23 1.377(2) . ?
C22 C27 1.382(2) . ?
C22 O2 1.403(2) . ?
C27 C26 1.390(3) . ?
C27 H27 0.95 . ?
C26 C25 1.373(3) . ?
C26 H26 0.95 . ?
C25 C24 1.381(3) . ?
C25 H25 0.95 . ?
C24 C23 1.391(3) . ?
C24 H24 0.95 . ?
C23 H23 0.95 . ?
N1 N3 1.3723(19) . ?
N2 H102 0.904(9) . ?
N2 H202 0.900(10) . ?
N4 P1 1.5611(14) . ?
N4 P2 1.5720(13) . ?
O1 P2 1.4720(12) . ?
O2 P2 1.6014(12) . ?
O3 P2 1.5986(12) . ?

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
N3 C1 S1 114.55(12) . . ?
N3 C1 P1 125.31(12) . . ?
S1 C1 P1 119.63(9) . . ?
N2 C3 N1 123.73(15) . . ?
N2 C3 S1 122.55(12) . . ?
N1 C3 S1 113.71(12) . . ?
C17 C16 C21 121.56(17) . . ?
C17 C16 O3 117.76(16) . . ?
C21 C16 O3 120.66(16) . . ?
C16 C17 C18 119.23(19) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 120.20(19) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.74(19) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.7(2) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 118.52(19) . . ?
C16 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C5 C4 C9 119.41(16) . . ?
C5 C4 P1 122.87(13) . . ?
C9 C4 P1 117.72(13) . . ?
C6 C5 C4 120.14(18) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.00(19) . . ?
C7 C6 H6 120 . . ?
C5 C6 H6 120 . . ?
C6 C7 C8 120.44(17) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 119.96(18) . . ?
C7 C8 H8 120 . . ?
C9 C8 H8 120 . . ?
C8 C9 C4 120.05(17) . . ?
C8 C9 H9 120 . . ?
C4 C9 H9 120 . . ?
C15 C10 C11 119.79(16) . . ?
C15 C10 P1 119.51(13) . . ?
C11 C10 P1 120.66(13) . . ?
C12 C11 C10 119.64(18) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.33(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.08(18) . . ?
C14 C13 H13 120 . . ?
C12 C13 H13 120 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.83(18) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C23 C22 C27 121.43(16) . . ?
C23 C22 O2 116.15(15) . . ?
C27 C22 O2 122.32(15) . . ?
C22 C27 C26 118.84(17) . . ?
C22 C27 H27 120.6 . . ?
C26 C27 H27 120.6 . . ?
C25 C26 C27 120.58(18) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C25 C24 119.86(18) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C24 C23 120.49(18) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C22 C23 C24 118.79(18) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C3 N1 N3 111.85(13) . . ?
C3 N2 H102 117.9(12) . . ?
C3 N2 H202 117.9(15) . . ?
H102 N2 H202 124(2) . . ?
C1 N3 N1 113.39(13) . . ?
P1 N4 P2 143.33(10) . . ?
C22 O2 P2 123.85(10) . . ?
C16 O3 P2 121.09(10) . . ?
O1 P2 N4 120.87(7) . . ?
O1 P2 O3 106.88(7) . . ?
N4 P2 O3 106.30(7) . . ?
O1 P2 O2 111.42(7) . . ?
N4 P2 O2 105.11(7) . . ?
O3 P2 O2 105.15(6) . . ?
N4 P1 C10 110.82(8) . . ?
N4 P1 C1 108.61(7) . . ?
C10 P1 C1 108.44(7) . . ?
N4 P1 C4 116.28(7) . . ?
C10 P1 C4 106.78(7) . . ?
C1 P1 C4 105.56(8) . . ?
C1 S1 C3 86.43(8) . . ?


# END of CIF
