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

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

data_x1735
_database_code_depnum_ccdc_archive 'CCDC 989748'
_audit_update_record             
;
2014-03-03 deposited with the CCDC.
2015-07-30 downloaded from the CCDC.
;

_audit_creation_date             2014-01-24T13:59:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C10 H17 O2 P S'
_chemical_formula_weight         232.27
_chemical_absolute_configuration rmad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.76820(10)
_cell_length_b                   9.09480(10)
_cell_length_c                   14.4718(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1154.05(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    14867
_cell_measurement_theta_min      2.8093
_cell_measurement_theta_max      37.4907

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

_exptl_crystal_description       'thin needles'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.9912
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.356
_diffrn_orient_matrix_ub_11      -0.0468249
_diffrn_orient_matrix_ub_12      0.0004825
_diffrn_orient_matrix_ub_13      -0.0399771
_diffrn_orient_matrix_ub_21      -0.0647929
_diffrn_orient_matrix_ub_22      0.0142726
_diffrn_orient_matrix_ub_23      0.0279528
_diffrn_orient_matrix_ub_31      0.0123702
_diffrn_orient_matrix_ub_32      0.0766475
_diffrn_orient_matrix_ub_33      -0.0049179
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_number            29094
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3519
_reflns_number_gt                3382
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SIR92 (Giacovazzo 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 for Windows (L. J. Farrugia, 1997)'
_computing_publication_material  'WINGX  (L.J. 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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0332P)²+0.1156P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3519
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.024
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0594
_refine_ls_wR_factor_gt          0.0588
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.004
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   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
S S 0.1246 0.1234 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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 0.34266(4) 0.05052(3) 0.40864(2) 0.03628(9) Uani 1 1 d . . .
P1 P 0.36930(3) 0.26272(3) 0.405076(18) 0.02061(6) Uani 1 1 d . . .
O1 O 0.13678(11) 0.68550(9) 0.26409(7) 0.03125(19) Uani 1 1 d . . .
O2 O -0.02075(10) 0.44210(10) 0.30181(7) 0.03143(19) Uani 1 1 d . . .
C1 C 0.24700(12) 0.37320(10) 0.32804(7) 0.01884(18) Uani 1 1 d . . .
C2 C 0.33672(11) 0.52170(11) 0.32088(7) 0.01762(17) Uani 1 1 d . . .
C3 C 0.47912(11) 0.51162(11) 0.38775(7) 0.01917(18) Uani 1 1 d . . .
C4 C 0.41942(12) 0.50330(11) 0.48703(7) 0.01946(18) Uani 1 1 d . . .
C5 C 0.35703(12) 0.37306(11) 0.50748(7) 0.02162(19) Uani 1 1 d . . .
C6 C 0.54070(13) 0.35567(13) 0.36835(8) 0.0245(2) Uani 1 1 d . . .
C7 C 0.24178(13) 0.65873(12) 0.33753(8) 0.0227(2) Uani 1 1 d . . .
C8 C 0.08400(13) 0.37553(13) 0.36476(8) 0.0251(2) Uani 1 1 d . . .
C9 C 0.59892(13) 0.62888(14) 0.37027(10) 0.0303(3) Uani 1 1 d . . .
C10 C 0.42874(16) 0.63125(13) 0.55148(9) 0.0313(3) Uani 1 1 d . . .
H1 H 0.2446(15) 0.3289(16) 0.2698(10) 0.024(3) Uiso 1 1 d . . .
H2 H 0.3831(16) 0.5293(15) 0.2570(10) 0.021(3) Uiso 1 1 d . . .
H3 H 0.083(2) 0.620(2) 0.2663(13) 0.044(5) Uiso 1 1 d . . .
H4 H -0.068(2) 0.372(2) 0.2721(14) 0.053(5) Uiso 1 1 d . . .
H5 H 0.3030(18) 0.3496(18) 0.5641(11) 0.031(4) Uiso 1 1 d . . .
H6A H 0.5613(17) 0.3390(17) 0.3062(10) 0.029(4) Uiso 1 1 d . . .
H6B H 0.6273(18) 0.3374(18) 0.4087(11) 0.035(4) Uiso 1 1 d . . .
H7A H 0.3029(17) 0.7380(16) 0.3393(9) 0.022(3) Uiso 1 1 d . . .
H7B H 0.1910(15) 0.6527(15) 0.3933(9) 0.017(3) Uiso 1 1 d . . .
H8A H 0.0756(16) 0.4325(15) 0.4220(10) 0.019(3) Uiso 1 1 d . . .
H8B H 0.0510(18) 0.2801(17) 0.3763(11) 0.030(4) Uiso 1 1 d . . .
H9A H 0.402(2) 0.723(2) 0.5224(12) 0.043(5) Uiso 1 1 d . . .
H9B H 0.531(2) 0.644(2) 0.5693(13) 0.048(5) Uiso 1 1 d . . .
H9C H 0.3699(18) 0.6172(19) 0.6048(11) 0.035(4) Uiso 1 1 d . . .
H10A H 0.6313(19) 0.6246(19) 0.3075(12) 0.037(4) Uiso 1 1 d . . .
H10B H 0.5555(17) 0.7292(17) 0.3818(10) 0.027(4) Uiso 1 1 d . . .
H10C H 0.686(2) 0.612(2) 0.4120(12) 0.042(4) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 P1 1.9447(4) . ?
P1 C5 1.7929(11) . ?
P1 C6 1.8044(12) . ?
P1 C1 1.8446(11) . ?
O1 C7 1.4271(13) . ?
O1 H3 0.756(19) . ?
O2 C8 1.4283(14) . ?
O2 H4 0.87(2) . ?
C1 C8 1.5250(15) . ?
C1 C2 1.5664(14) . ?
C1 H1 0.934(14) . ?
C2 C7 1.5180(14) . ?
C2 C3 1.5824(14) . ?
C2 H2 1.012(14) . ?
C3 C9 1.5181(15) . ?
C3 C4 1.5309(14) . ?
C3 C6 1.5433(15) . ?
C4 C5 1.3379(14) . ?
C4 C10 1.4936(15) . ?
C5 H5 0.970(16) . ?
C6 H6A 0.929(15) . ?
C6 H6B 0.973(16) . ?
C7 H7A 0.899(15) . ?
C7 H7B 0.923(13) . ?
C8 H8A 0.980(14) . ?
C8 H8B 0.930(16) . ?
C9 H10A 0.953(17) . ?
C9 H10B 1.003(16) . ?
C9 H10C 0.985(18) . ?
C10 H9A 0.963(18) . ?
C10 H9B 0.937(19) . ?
C10 H9C 0.937(17) . ?

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
C5 P1 C6 91.79(5) . . ?
C5 P1 C1 99.19(5) . . ?
C6 P1 C1 92.92(5) . . ?
C5 P1 S1 121.76(4) . . ?
C6 P1 S1 124.95(4) . . ?
C1 P1 S1 119.13(3) . . ?
C7 O1 H3 103.6(14) . . ?
C8 O2 H4 108.2(13) . . ?
C8 C1 C2 118.80(8) . . ?
C8 C1 P1 109.99(7) . . ?
C2 C1 P1 102.57(6) . . ?
C8 C1 H1 107.4(8) . . ?
C2 C1 H1 108.9(9) . . ?
P1 C1 H1 108.9(9) . . ?
C7 C2 C1 114.96(8) . . ?
C7 C2 C3 112.53(8) . . ?
C1 C2 C3 107.81(8) . . ?
C7 C2 H2 108.0(8) . . ?
C1 C2 H2 108.8(8) . . ?
C3 C2 H2 104.2(8) . . ?
C9 C3 C4 115.32(9) . . ?
C9 C3 C6 111.91(9) . . ?
C4 C3 C6 104.18(8) . . ?
C9 C3 C2 113.79(9) . . ?
C4 C3 C2 107.88(8) . . ?
C6 C3 C2 102.59(8) . . ?
C5 C4 C10 125.03(10) . . ?
C5 C4 C3 113.02(9) . . ?
C10 C4 C3 121.93(9) . . ?
C4 C5 P1 106.75(8) . . ?
C4 C5 H5 125.5(9) . . ?
P1 C5 H5 127.2(9) . . ?
C3 C6 P1 94.91(7) . . ?
C3 C6 H6A 113.2(10) . . ?
P1 C6 H6A 111.8(10) . . ?
C3 C6 H6B 108.7(10) . . ?
P1 C6 H6B 113.2(9) . . ?
H6A C6 H6B 113.7(13) . . ?
O1 C7 C2 112.06(9) . . ?
O1 C7 H7A 105.6(9) . . ?
C2 C7 H7A 109.6(9) . . ?
O1 C7 H7B 110.5(8) . . ?
C2 C7 H7B 110.8(9) . . ?
H7A C7 H7B 108.1(12) . . ?
O2 C8 C1 112.73(9) . . ?
O2 C8 H8A 105.5(8) . . ?
C1 C8 H8A 111.8(8) . . ?
O2 C8 H8B 108.1(10) . . ?
C1 C8 H8B 110.0(10) . . ?
H8A C8 H8B 108.5(12) . . ?
C3 C9 H10A 109.6(10) . . ?
C3 C9 H10B 110.4(9) . . ?
H10A C9 H10B 108.0(13) . . ?
C3 C9 H10C 109.0(10) . . ?
H10A C9 H10C 110.4(14) . . ?
H10B C9 H10C 109.4(13) . . ?
C4 C10 H9A 112.9(11) . . ?
C4 C10 H9B 108.8(12) . . ?
H9A C10 H9B 104.2(15) . . ?
C4 C10 H9C 112.2(10) . . ?
H9A C10 H9C 110.0(15) . . ?
H9B C10 H9C 108.4(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 P1 C1 C8 -64.00(8) . . . . ?
C6 P1 C1 C8 -156.29(7) . . . . ?
S1 P1 C1 C8 70.47(8) . . . . ?
C5 P1 C1 C2 63.33(7) . . . . ?
C6 P1 C1 C2 -28.96(7) . . . . ?
S1 P1 C1 C2 -162.20(5) . . . . ?
C8 C1 C2 C7 -9.32(13) . . . . ?
P1 C1 C2 C7 -130.80(8) . . . . ?
C8 C1 C2 C3 117.08(10) . . . . ?
P1 C1 C2 C3 -4.40(9) . . . . ?
C7 C2 C3 C9 -67.36(11) . . . . ?
C1 C2 C3 C9 164.83(9) . . . . ?
C7 C2 C3 C4 61.93(11) . . . . ?
C1 C2 C3 C4 -65.88(10) . . . . ?
C7 C2 C3 C6 171.56(8) . . . . ?
C1 C2 C3 C6 43.74(10) . . . . ?
C9 C3 C4 C5 -158.58(10) . . . . ?
C6 C3 C4 C5 -35.53(11) . . . . ?
C2 C3 C4 C5 73.00(11) . . . . ?
C9 C3 C4 C10 22.79(14) . . . . ?
C6 C3 C4 C10 145.84(11) . . . . ?
C2 C3 C4 C10 -105.63(11) . . . . ?
C10 C4 C5 P1 177.81(9) . . . . ?
C3 C4 C5 P1 -0.77(11) . . . . ?
C6 P1 C5 C4 29.92(8) . . . . ?
C1 P1 C5 C4 -63.33(8) . . . . ?
S1 P1 C5 C4 163.82(6) . . . . ?
C9 C3 C6 P1 176.44(8) . . . . ?
C4 C3 C6 P1 51.20(8) . . . . ?
C2 C3 C6 P1 -61.19(8) . . . . ?
C5 P1 C6 C3 -46.27(7) . . . . ?
C1 P1 C6 C3 53.03(7) . . . . ?
S1 P1 C6 C3 -177.89(5) . . . . ?
C1 C2 C7 O1 -70.10(12) . . . . ?
C3 C2 C7 O1 165.97(9) . . . . ?
C2 C1 C8 O2 70.42(12) . . . . ?
P1 C1 C8 O2 -171.92(7) . . . . ?
####################################################################### 
# 
# 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_x1746
_database_code_depnum_ccdc_archive 'CCDC 989749'
_audit_update_record             
;
2014-03-03 deposited with the CCDC.
2015-07-30 downloaded from the CCDC.
;

_audit_creation_date             2014-01-24T12:58:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C10 H17 O2 P S'
_chemical_formula_weight         232.27
_chemical_absolute_configuration rmad

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2
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'

_cell_length_a                   14.9910(2)
_cell_length_b                   7.39940(10)
_cell_length_c                   10.5296(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.7460(10)
_cell_angle_gamma                90
_cell_volume                     1165.49(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    13759
_cell_measurement_theta_min      3.0652
_cell_measurement_theta_max      37.4287

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

_exptl_crystal_description       'thin needles'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.98194
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.356
_diffrn_orient_matrix_ub_11      0.0384734
_diffrn_orient_matrix_ub_12      -0.0515469
_diffrn_orient_matrix_ub_13      0.0190434
_diffrn_orient_matrix_ub_21      -0.0273094
_diffrn_orient_matrix_ub_22      -0.076939
_diffrn_orient_matrix_ub_23      0.007766
_diffrn_orient_matrix_ub_31      0.0048863
_diffrn_orient_matrix_ub_32      -0.0245242
_diffrn_orient_matrix_ub_33      -0.0643105
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_number            20098
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3539
_reflns_number_gt                3458
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SIR92 (Giacovazzo 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 for Windows (L. J. Farrugia, 1997)'
_computing_publication_material  'WINGX  (L.J. 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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0343P)²+0.2680P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3539
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0566
_refine_ls_wR_factor_gt          0.0561
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   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
S S 0.1246 0.1234 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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 0.879404(17) 0.40175(4) 0.94876(3) 0.02681(7) Uani 1 1 d . . .
P1 P 0.763423(15) 0.42365(3) 0.85461(2) 0.01769(6) Uani 1 1 d . . .
O1 O 0.62054(5) 0.41064(16) 0.57878(7) 0.02929(17) Uani 1 1 d . . .
O2 O 0.77604(7) 0.85990(12) 0.62581(9) 0.03062(19) Uani 1 1 d . . .
C1 C 0.73519(7) 0.63972(14) 0.77761(10) 0.01745(18) Uani 1 1 d . . .
C2 C 0.63241(7) 0.62376(15) 0.74494(9) 0.01935(18) Uani 1 1 d . . .
C3 C 0.59938(6) 0.44203(15) 0.80088(9) 0.01953(19) Uani 1 1 d . . .
C4 C 0.62974(7) 0.30763(16) 0.69725(11) 0.0238(2) Uani 1 1 d . . .
C5 C 0.73011(8) 0.26390(16) 0.72970(13) 0.0254(2) Uani 1 1 d . . .
C6 C 0.65666(6) 0.40502(16) 0.92446(9) 0.02031(17) Uani 1 1 d . . .
C7 C 0.60543(8) 0.5986(2) 0.60499(11) 0.0281(2) Uani 1 1 d . . .
C8 C 0.79462(7) 0.68128(15) 0.66967(10) 0.02165(19) Uani 1 1 d . . .
C9 C 0.49902(7) 0.4417(2) 0.81822(11) 0.0288(2) Uani 1 1 d . . .
C10 C 0.57492(9) 0.1359(2) 0.67874(15) 0.0363(3) Uani 1 1 d . . .
H1 H 0.7486(10) 0.723(2) 0.8437(14) 0.020(3) Uiso 1 1 d . . .
H2 H 0.6007(10) 0.725(2) 0.7865(14) 0.020(3) Uiso 1 1 d . . .
H5A H 0.7372(11) 0.161(3) 0.7667(16) 0.027(4) Uiso 1 1 d . . .
H5B H 0.7639(14) 0.275(3) 0.6570(19) 0.045(5) Uiso 1 1 d . . .
H6A H 0.6506(10) 0.505(2) 0.9893(15) 0.021(4) Uiso 1 1 d . . .
H6B H 0.6444(10) 0.292(2) 0.9558(14) 0.018(3) Uiso 1 1 d . . .
H7A H 0.5427(12) 0.631(3) 0.5882(17) 0.034(4) Uiso 1 1 d . . .
H7B H 0.6378(11) 0.668(3) 0.5492(16) 0.036(4) Uiso 1 1 d . . .
H8A H 0.7817(11) 0.583(2) 0.5944(15) 0.023(4) Uiso 1 1 d . . .
H8B H 0.8588(10) 0.664(2) 0.7013(14) 0.022(3) Uiso 1 1 d . . .
H9A H 0.4810(12) 0.321(2) 0.8612(17) 0.029(4) Uiso 1 1 d . . .
H9B H 0.4831(13) 0.544(2) 0.8733(19) 0.032(4) Uiso 1 1 d . . .
H9C H 0.4668(12) 0.455(2) 0.7398(18) 0.039(5) Uiso 1 1 d . . .
H10A H 0.5783(17) 0.065(3) 0.760(2) 0.064(7) Uiso 1 1 d . . .
H10B H 0.6010(14) 0.061(3) 0.610(2) 0.050(6) Uiso 1 1 d . . .
H10C H 0.5172(13) 0.166(3) 0.6465(17) 0.038(4) Uiso 1 1 d . . .
H11 H 0.8047(14) 0.884(3) 0.574(2) 0.056(6) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 P1 1.9511(3) . ?
P1 C6 1.8098(9) . ?
P1 C5 1.8140(12) . ?
P1 C1 1.8298(11) . ?
O1 C7 1.4391(18) . ?
O1 C4 1.4607(15) . ?
O2 C8 1.4216(14) . ?
O2 H11 0.74(2) . ?
C1 C8 1.5207(14) . ?
C1 C2 1.5610(15) . ?
C1 H1 0.943(16) . ?
C2 C7 1.5138(15) . ?
C2 C3 1.5616(15) . ?
C2 H2 1.005(15) . ?
C3 C9 1.5274(14) . ?
C3 C6 1.5361(14) . ?
C3 C4 1.5658(14) . ?
C4 C10 1.5186(17) . ?
C4 C5 1.5551(16) . ?
C5 H5A 0.860(19) . ?
C5 H5B 0.95(2) . ?
C6 H6A 1.017(16) . ?
C6 H6B 0.923(16) . ?
C7 H7A 0.975(19) . ?
C7 H7B 0.937(18) . ?
C8 H8A 1.082(16) . ?
C8 H8B 1.005(15) . ?
C9 H9A 1.043(18) . ?
C9 H9B 0.992(19) . ?
C9 H9C 0.934(19) . ?
C10 H10A 1.00(3) . ?
C10 H10B 1.01(2) . ?
C10 H10C 0.94(2) . ?

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
C6 P1 C5 92.07(5) . . ?
C6 P1 C1 93.53(5) . . ?
C5 P1 C1 101.73(6) . . ?
C6 P1 S1 124.72(3) . . ?
C5 P1 S1 120.55(4) . . ?
C1 P1 S1 118.06(4) . . ?
C7 O1 C4 110.36(8) . . ?
C8 O2 H11 110.8(19) . . ?
C8 C1 C2 117.94(9) . . ?
C8 C1 P1 112.21(7) . . ?
C2 C1 P1 103.18(7) . . ?
C8 C1 H1 108.2(9) . . ?
C2 C1 H1 111.8(9) . . ?
P1 C1 H1 102.4(9) . . ?
C7 C2 C1 114.89(9) . . ?
C7 C2 C3 100.97(9) . . ?
C1 C2 C3 108.35(8) . . ?
C7 C2 H2 114.3(9) . . ?
C1 C2 H2 109.6(9) . . ?
C3 C2 H2 108.0(8) . . ?
C9 C3 C6 113.51(8) . . ?
C9 C3 C2 112.68(10) . . ?
C6 C3 C2 107.43(8) . . ?
C9 C3 C4 114.56(9) . . ?
C6 C3 C4 107.78(9) . . ?
C2 C3 C4 99.80(8) . . ?
O1 C4 C10 107.87(10) . . ?
O1 C4 C5 109.41(9) . . ?
C10 C4 C5 111.21(11) . . ?
O1 C4 C3 104.37(9) . . ?
C10 C4 C3 116.19(9) . . ?
C5 C4 C3 107.46(9) . . ?
C4 C5 P1 103.90(7) . . ?
C4 C5 H5A 111.9(12) . . ?
P1 C5 H5A 103.3(12) . . ?
C4 C5 H5B 111.4(12) . . ?
P1 C5 H5B 113.2(13) . . ?
H5A C5 H5B 112.6(17) . . ?
C3 C6 P1 95.88(6) . . ?
C3 C6 H6A 111.7(9) . . ?
P1 C6 H6A 109.7(9) . . ?
C3 C6 H6B 110.6(9) . . ?
P1 C6 H6B 114.6(9) . . ?
H6A C6 H6B 113.2(13) . . ?
O1 C7 C2 105.66(10) . . ?
O1 C7 H7A 111.2(11) . . ?
C2 C7 H7A 109.9(10) . . ?
O1 C7 H7B 108.1(11) . . ?
C2 C7 H7B 115.3(11) . . ?
H7A C7 H7B 106.7(15) . . ?
O2 C8 C1 108.59(9) . . ?
O2 C8 H8A 111.3(8) . . ?
C1 C8 H8A 109.0(9) . . ?
O2 C8 H8B 112.8(9) . . ?
C1 C8 H8B 108.8(9) . . ?
H8A C8 H8B 106.3(12) . . ?
C3 C9 H9A 109.8(10) . . ?
C3 C9 H9B 110.2(11) . . ?
H9A C9 H9B 108.6(12) . . ?
C3 C9 H9C 110.5(11) . . ?
H9A C9 H9C 109.8(16) . . ?
H9B C9 H9C 107.9(16) . . ?
C4 C10 H10A 109.3(14) . . ?
C4 C10 H10B 108.6(12) . . ?
H10A C10 H10B 109.1(19) . . ?
C4 C10 H10C 109.0(13) . . ?
H10A C10 H10C 115.4(18) . . ?
H10B C10 H10C 105.2(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 P1 C1 C8 -160.82(8) . . . . ?
C5 P1 C1 C8 -67.97(8) . . . . ?
S1 P1 C1 C8 66.37(8) . . . . ?
C6 P1 C1 C2 -32.84(7) . . . . ?
C5 P1 C1 C2 60.02(8) . . . . ?
S1 P1 C1 C2 -165.64(5) . . . . ?
C8 C1 C2 C7 16.68(14) . . . . ?
P1 C1 C2 C7 -107.63(10) . . . . ?
C8 C1 C2 C3 128.70(9) . . . . ?
P1 C1 C2 C3 4.39(9) . . . . ?
C7 C2 C3 C9 -79.83(10) . . . . ?
C1 C2 C3 C9 159.10(9) . . . . ?
C7 C2 C3 C6 154.41(8) . . . . ?
C1 C2 C3 C6 33.34(10) . . . . ?
C7 C2 C3 C4 42.13(10) . . . . ?
C1 C2 C3 C4 -78.93(9) . . . . ?
C7 O1 C4 C10 135.45(10) . . . . ?
C7 O1 C4 C5 -103.44(10) . . . . ?
C7 O1 C4 C3 11.31(11) . . . . ?
C9 C3 C4 O1 87.46(11) . . . . ?
C6 C3 C4 O1 -145.16(8) . . . . ?
C2 C3 C4 O1 -33.15(9) . . . . ?
C9 C3 C4 C10 -31.15(15) . . . . ?
C6 C3 C4 C10 96.23(12) . . . . ?
C2 C3 C4 C10 -151.77(11) . . . . ?
C9 C3 C4 C5 -156.42(10) . . . . ?
C6 C3 C4 C5 -29.04(12) . . . . ?
C2 C3 C4 C5 82.96(10) . . . . ?
O1 C4 C5 P1 102.97(9) . . . . ?
C10 C4 C5 P1 -137.97(9) . . . . ?
C3 C4 C5 P1 -9.78(11) . . . . ?
C6 P1 C5 C4 37.24(9) . . . . ?
C1 P1 C5 C4 -56.79(9) . . . . ?
S1 P1 C5 C4 170.33(6) . . . . ?
C9 C3 C6 P1 -179.09(9) . . . . ?
C2 C3 C6 P1 -53.82(8) . . . . ?
C4 C3 C6 P1 52.92(9) . . . . ?
C5 P1 C6 C3 -51.86(8) . . . . ?
C1 P1 C6 C3 50.03(7) . . . . ?
S1 P1 C6 C3 178.06(5) . . . . ?
C4 O1 C7 C2 16.51(11) . . . . ?
C1 C2 C7 O1 79.20(11) . . . . ?
C3 C2 C7 O1 -37.12(10) . . . . ?
C2 C1 C8 O2 67.51(12) . . . . ?
P1 C1 C8 O2 -172.80(8) . . . . ?
####################################################################### 
# 
# 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_x1798
_database_code_depnum_ccdc_archive 'CCDC 989750'
_audit_update_record             
;
2014-03-03 deposited with the CCDC.
2015-07-30 downloaded from the CCDC.
;

_audit_creation_date             2014-01-25T14:14:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C16 H21 O2 P S'
_chemical_formula_weight         308.36
_chemical_absolute_configuration rmad

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

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

_cell_length_a                   8.196(5)
_cell_length_b                   8.334(5)
_cell_length_c                   11.144(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 92.054
_cell_angle_gamma                90.000
_cell_volume                     760.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    7521
_cell_measurement_theta_min      1.818
_cell_measurement_theta_max      34.337

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

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.99464
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.356
_diffrn_orient_matrix_ub_11      -0.0339429
_diffrn_orient_matrix_ub_12      -0.0406898
_diffrn_orient_matrix_ub_13      0.0491324
_diffrn_orient_matrix_ub_21      -0.0722437
_diffrn_orient_matrix_ub_22      -0.0148934
_diffrn_orient_matrix_ub_23      -0.0351464
_diffrn_orient_matrix_ub_31      0.0335503
_diffrn_orient_matrix_ub_32      -0.0732657
_diffrn_orient_matrix_ub_33      -0.02018
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_number            13043
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         30.5
_diffrn_reflns_theta_full        30.5
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             4636
_reflns_number_gt                4363
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR92 (Giacovazzo 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 for Windows (L. J. Farrugia, 1997)'
_computing_publication_material  'WINGX  (L.J. 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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0339P)²+0.0467P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4636
_refine_ls_number_parameters     265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.064
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   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
S S 0.1246 0.1234 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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 0.12372(4) 0.79184(4) 0.38957(4) 0.02589(8) Uani 1 1 d . . .
P1 P 0.20187(4) 0.57774(4) 0.35525(3) 0.01485(7) Uani 1 1 d . . .
O2 O -0.07857(13) 0.41759(13) 0.07013(9) 0.0231(2) Uani 1 1 d . . .
O1 O 0.04445(14) 0.12626(12) 0.12150(10) 0.0241(2) Uani 1 1 d . . .
C1 C 0.06959(15) 0.43826(15) 0.26766(11) 0.0151(2) Uani 1 1 d . . .
C2 C 0.15511(15) 0.27245(14) 0.29126(11) 0.0156(2) Uani 1 1 d . . .
C3 C 0.31269(15) 0.30451(15) 0.37381(11) 0.0159(2) Uani 1 1 d . . .
C4 C 0.43814(15) 0.39763(15) 0.30220(11) 0.0156(2) Uani 1 1 d . . .
C5 C 0.39439(14) 0.55199(14) 0.28248(11) 0.0143(2) Uani 1 1 d . . .
C6 C 0.25221(16) 0.42707(17) 0.46625(11) 0.0184(2) Uani 1 1 d . . .
C7 C 0.19401(17) 0.17409(16) 0.18169(12) 0.0196(3) Uani 1 1 d . . .
C8 C 0.04621(17) 0.49825(16) 0.13933(12) 0.0182(2) Uani 1 1 d . . .
C9 C 0.37921(19) 0.15310(17) 0.43386(14) 0.0240(3) Uani 1 1 d . . .
C10 C 0.58655(17) 0.31634(17) 0.25794(14) 0.0234(3) Uani 1 1 d . . .
C11 C 0.48031(16) 0.67905(14) 0.21728(11) 0.0157(2) Uani 1 1 d . . .
C12 C 0.64498(17) 0.71092(17) 0.24207(13) 0.0202(3) Uani 1 1 d . . .
C13 C 0.72377(19) 0.83599(17) 0.18564(14) 0.0251(3) Uani 1 1 d . . .
C14 C 0.63905(19) 0.92997(18) 0.10171(13) 0.0254(3) Uani 1 1 d . . .
C15 C 0.47636(19) 0.89848(16) 0.07395(13) 0.0235(3) Uani 1 1 d . . .
C16 C 0.39688(17) 0.77542(16) 0.13248(12) 0.0192(2) Uani 1 1 d . . .
H1 H -0.0414(19) 0.438(2) 0.3069(14) 0.017(4) Uiso 1 1 d . . .
H2 H 0.0843(19) 0.210(2) 0.3384(14) 0.015(4) Uiso 1 1 d . . .
H6A H 0.155(2) 0.388(2) 0.5058(16) 0.023(4) Uiso 1 1 d . . .
H6B H 0.340(2) 0.461(2) 0.5238(15) 0.019(4) Uiso 1 1 d . . .
H7A H 0.255(2) 0.081(3) 0.2025(15) 0.024(4) Uiso 1 1 d . . .
H7B H 0.2600(19) 0.234(2) 0.1234(15) 0.017(4) Uiso 1 1 d . . .
H8A H 0.0136(18) 0.6077(19) 0.1403(13) 0.010(3) Uiso 1 1 d . . .
H8B H 0.1478(19) 0.4882(19) 0.1006(14) 0.012(4) Uiso 1 1 d . . .
H9A H 0.294(2) 0.107(2) 0.4729(17) 0.029(5) Uiso 1 1 d . . .
H9B H 0.420(2) 0.071(3) 0.3738(17) 0.035(5) Uiso 1 1 d . . .
H9C H 0.474(2) 0.183(3) 0.4928(19) 0.027(4) Uiso 1 1 d . . .
H10A H 0.660(2) 0.284(3) 0.3252(17) 0.031(5) Uiso 1 1 d . . .
H10B H 0.555(2) 0.219(2) 0.2252(16) 0.026(5) Uiso 1 1 d . . .
H10C H 0.645(2) 0.381(2) 0.2033(17) 0.028(5) Uiso 1 1 d . . .
H12 H 0.701(2) 0.654(2) 0.3010(17) 0.026(5) Uiso 1 1 d . . .
H13 H 0.840(2) 0.851(2) 0.2082(17) 0.029(5) Uiso 1 1 d . . .
H14 H 0.688(2) 1.012(3) 0.0672(18) 0.035(5) Uiso 1 1 d . . .
H15 H 0.4153(19) 0.962(2) 0.0126(15) 0.021(4) Uiso 1 1 d . . .
H16 H 0.293(2) 0.760(2) 0.1187(15) 0.018(4) Uiso 1 1 d . . .
H17 H -0.059(3) 0.321(3) 0.070(2) 0.049(7) Uiso 1 1 d . . .
H18 H 0.068(3) 0.060(3) 0.077(2) 0.040(6) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 P1 1.9385(11) . ?
P1 C6 1.8001(15) . ?
P1 C5 1.8125(15) . ?
P1 C1 1.8449(14) . ?
O2 C8 1.4269(17) . ?
O2 H17 0.82(3) . ?
O1 C7 1.4326(18) . ?
O1 H18 0.77(2) . ?
C1 C8 1.5206(18) . ?
C1 C2 1.5674(19) . ?
C1 H1 1.024(16) . ?
C2 C7 1.5141(19) . ?
C2 C3 1.5813(18) . ?
C2 H2 0.953(17) . ?
C3 C9 1.5202(19) . ?
C3 C4 1.5347(18) . ?
C3 C6 1.5449(19) . ?
C4 C5 1.3514(18) . ?
C4 C10 1.4916(19) . ?
C5 C11 1.4771(18) . ?
C6 H6A 0.977(18) . ?
C6 H6B 0.986(17) . ?
C7 H7A 0.95(2) . ?
C7 H7B 0.993(17) . ?
C8 H8A 0.950(15) . ?
C8 H8B 0.955(16) . ?
C9 H9A 0.92(2) . ?
C9 H9B 1.02(2) . ?
C9 H9C 1.029(19) . ?
C10 H10A 0.98(2) . ?
C10 H10B 0.920(19) . ?
C10 H10C 0.956(19) . ?
C11 C12 1.393(2) . ?
C11 C16 1.3998(18) . ?
C12 C13 1.388(2) . ?
C12 H12 0.916(18) . ?
C13 C14 1.387(2) . ?
C13 H13 0.982(19) . ?
C14 C15 1.383(2) . ?
C14 H14 0.89(2) . ?
C15 C16 1.3900(19) . ?
C15 H15 0.988(17) . ?
C16 H16 0.871(17) . ?

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
C6 P1 C5 92.47(6) . . ?
C6 P1 C1 92.29(7) . . ?
C5 P1 C1 101.14(6) . . ?
C6 P1 S1 125.15(6) . . ?
C5 P1 S1 119.76(4) . . ?
C1 P1 S1 119.49(5) . . ?
C8 O2 H17 108.8(16) . . ?
C7 O1 H18 105.6(16) . . ?
C8 C1 C2 119.22(11) . . ?
C8 C1 P1 110.02(9) . . ?
C2 C1 P1 102.47(9) . . ?
C8 C1 H1 108.7(9) . . ?
C2 C1 H1 108.8(10) . . ?
P1 C1 H1 107.0(9) . . ?
C7 C2 C1 116.60(11) . . ?
C7 C2 C3 111.68(11) . . ?
C1 C2 C3 107.44(10) . . ?
C7 C2 H2 107.3(10) . . ?
C1 C2 H2 107.4(10) . . ?
C3 C2 H2 105.8(9) . . ?
C9 C3 C4 114.34(11) . . ?
C9 C3 C6 111.95(11) . . ?
C4 C3 C6 104.44(10) . . ?
C9 C3 C2 112.86(11) . . ?
C4 C3 C2 109.35(10) . . ?
C6 C3 C2 102.99(10) . . ?
C5 C4 C10 126.40(12) . . ?
C5 C4 C3 112.78(11) . . ?
C10 C4 C3 120.78(11) . . ?
C4 C5 C11 129.35(12) . . ?
C4 C5 P1 105.67(9) . . ?
C11 C5 P1 124.98(9) . . ?
C3 C6 P1 94.25(9) . . ?
C3 C6 H6A 111.4(11) . . ?
P1 C6 H6A 111.9(11) . . ?
C3 C6 H6B 112.3(10) . . ?
P1 C6 H6B 113.0(10) . . ?
H6A C6 H6B 112.7(14) . . ?
O1 C7 C2 109.08(11) . . ?
O1 C7 H7A 108.6(11) . . ?
C2 C7 H7A 111.8(11) . . ?
O1 C7 H7B 108.1(9) . . ?
C2 C7 H7B 113.1(10) . . ?
H7A C7 H7B 106.0(14) . . ?
O2 C8 C1 114.65(11) . . ?
O2 C8 H8A 105.2(9) . . ?
C1 C8 H8A 109.3(9) . . ?
O2 C8 H8B 109.5(9) . . ?
C1 C8 H8B 108.3(9) . . ?
H8A C8 H8B 109.8(13) . . ?
C3 C9 H9A 106.7(12) . . ?
C3 C9 H9B 112.8(12) . . ?
H9A C9 H9B 107.7(17) . . ?
C3 C9 H9C 109.3(12) . . ?
H9A C9 H9C 111.5(17) . . ?
H9B C9 H9C 108.8(15) . . ?
C4 C10 H10A 111.0(11) . . ?
C4 C10 H10B 108.0(11) . . ?
H10A C10 H10B 102.4(16) . . ?
C4 C10 H10C 112.6(11) . . ?
H10A C10 H10C 109.7(15) . . ?
H10B C10 H10C 112.6(16) . . ?
C12 C11 C16 118.08(12) . . ?
C12 C11 C5 120.97(11) . . ?
C16 C11 C5 120.89(12) . . ?
C13 C12 C11 121.08(13) . . ?
C13 C12 H12 118.9(12) . . ?
C11 C12 H12 119.8(12) . . ?
C14 C13 C12 119.97(14) . . ?
C14 C13 H13 123.8(11) . . ?
C12 C13 H13 116.2(11) . . ?
C15 C14 C13 119.94(13) . . ?
C15 C14 H14 120.0(13) . . ?
C13 C14 H14 120.1(13) . . ?
C14 C15 C16 119.95(13) . . ?
C14 C15 H15 120.9(10) . . ?
C16 C15 H15 119.2(10) . . ?
C15 C16 C11 120.95(13) . . ?
C15 C16 H16 119.9(11) . . ?
C11 C16 H16 119.1(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 P1 C1 C8 -159.60(10) . . . . ?
C5 P1 C1 C8 -66.63(10) . . . . ?
S1 P1 C1 C8 67.20(10) . . . . ?
C6 P1 C1 C2 -31.82(9) . . . . ?
C5 P1 C1 C2 61.15(9) . . . . ?
S1 P1 C1 C2 -165.02(6) . . . . ?
C8 C1 C2 C7 -6.05(16) . . . . ?
P1 C1 C2 C7 -127.74(10) . . . . ?
C8 C1 C2 C3 120.14(12) . . . . ?
P1 C1 C2 C3 -1.55(11) . . . . ?
C7 C2 C3 C9 -68.02(14) . . . . ?
C1 C2 C3 C9 162.93(11) . . . . ?
C7 C2 C3 C4 60.45(13) . . . . ?
C1 C2 C3 C4 -68.60(12) . . . . ?
C7 C2 C3 C6 171.07(10) . . . . ?
C1 C2 C3 C6 42.02(12) . . . . ?
C9 C3 C4 C5 -160.33(11) . . . . ?
C6 C3 C4 C5 -37.63(13) . . . . ?
C2 C3 C4 C5 72.03(13) . . . . ?
C9 C3 C4 C10 21.89(16) . . . . ?
C6 C3 C4 C10 144.59(12) . . . . ?
C2 C3 C4 C10 -105.75(13) . . . . ?
C10 C4 C5 C11 -1.9(2) . . . . ?
C3 C4 C5 C11 -179.53(11) . . . . ?
C10 C4 C5 P1 178.61(11) . . . . ?
C3 C4 C5 P1 0.98(12) . . . . ?
C6 P1 C5 C4 29.12(9) . . . . ?
C1 P1 C5 C4 -63.71(10) . . . . ?
S1 P1 C5 C4 162.63(7) . . . . ?
C6 P1 C5 C11 -150.40(11) . . . . ?
C1 P1 C5 C11 116.78(11) . . . . ?
S1 P1 C5 C11 -16.89(12) . . . . ?
C9 C3 C6 P1 176.79(9) . . . . ?
C4 C3 C6 P1 52.55(10) . . . . ?
C2 C3 C6 P1 -61.69(9) . . . . ?
C5 P1 C6 C3 -46.56(8) . . . . ?
C1 P1 C6 C3 54.70(9) . . . . ?
S1 P1 C6 C3 -176.20(5) . . . . ?
C1 C2 C7 O1 -65.56(14) . . . . ?
C3 C2 C7 O1 170.39(10) . . . . ?
C2 C1 C8 O2 73.84(16) . . . . ?
P1 C1 C8 O2 -168.31(9) . . . . ?
C4 C5 C11 C12 -49.96(19) . . . . ?
P1 C5 C11 C12 129.44(12) . . . . ?
C4 C5 C11 C16 132.79(14) . . . . ?
P1 C5 C11 C16 -47.81(16) . . . . ?
C16 C11 C12 C13 0.9(2) . . . . ?
C5 C11 C12 C13 -176.44(12) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C16 1.7(2) . . . . ?
C14 C15 C16 C11 -1.8(2) . . . . ?
C12 C11 C16 C15 0.53(19) . . . . ?
C5 C11 C16 C15 177.86(12) . . . . ?
####################################################################### 
# 
# 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_x1778
_database_code_depnum_ccdc_archive 'CCDC 989751'
_audit_update_record             
;
2014-03-03 deposited with the CCDC.
2015-07-30 downloaded from the CCDC.
;

_audit_creation_date             2014-01-25T14:23:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C16 H21 O2 P S'
_chemical_formula_weight         308.36
_chemical_absolute_configuration rmad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.410(5)
_cell_length_b                   12.953(5)
_cell_length_c                   13.799(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_volume                     1503.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    7109
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      32.223

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

_exptl_crystal_description       'thin needles'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.32
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.8928
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.356
_diffrn_orient_matrix_ub_11      0.0207781
_diffrn_orient_matrix_ub_12      0.0503836
_diffrn_orient_matrix_ub_13      0.0156077
_diffrn_orient_matrix_ub_21      0.0034453
_diffrn_orient_matrix_ub_22      -0.0176814
_diffrn_orient_matrix_ub_23      0.0486082
_diffrn_orient_matrix_ub_31      0.0816612
_diffrn_orient_matrix_ub_32      -0.0121111
_diffrn_orient_matrix_ub_33      -0.0060704
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_number            18990
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         30.5
_diffrn_reflns_theta_full        30.5
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4571
_reflns_number_gt                4237
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SIR92 (Giacovazzo 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 for Windows (L. J. Farrugia, 1997)'
_computing_publication_material  'WINGX  (L.J. 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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0420P)²+0.1239P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4571
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0755
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   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
S S 0.1246 0.1234 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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 0.46279(5) 0.32743(3) 0.61507(3) 0.02674(9) Uani 1 1 d . . .
P1 P 0.43679(4) 0.37466(3) 0.48176(3) 0.01875(8) Uani 1 1 d . . .
O1 O 0.37048(14) 0.55986(8) 0.30101(8) 0.0281(2) Uani 1 1 d . . .
O2 O -0.04161(14) 0.42522(10) 0.44520(10) 0.0365(3) Uani 1 1 d . . .
C1 C 0.23705(17) 0.37521(12) 0.43211(11) 0.0223(3) Uani 1 1 d . . .
C2 C 0.26619(18) 0.39224(12) 0.32205(11) 0.0247(3) Uani 1 1 d . . .
C3 C 0.44788(17) 0.38328(10) 0.30189(9) 0.0203(2) Uani 1 1 d . . .
C4 C 0.50024(18) 0.49567(11) 0.33015(10) 0.0204(3) Uani 1 1 d . . .
C5 C 0.52783(16) 0.49591(10) 0.44323(10) 0.0182(2) Uani 1 1 d . . .
C6 C 0.51649(18) 0.30787(11) 0.37727(11) 0.0220(3) Uani 1 1 d . . .
C7 C 0.2306(2) 0.49953(15) 0.28446(13) 0.0315(4) Uani 1 1 d . . .
C8 C 0.11409(18) 0.44175(12) 0.48354(13) 0.0273(3) Uani 1 1 d . . .
C9 C 0.4830(2) 0.35355(13) 0.19747(12) 0.0289(3) Uani 1 1 d . . .
C10 C 0.6484(2) 0.53641(13) 0.27996(13) 0.0295(3) Uani 1 1 d . . .
C11 C 0.49692(15) 0.59039(10) 0.50544(10) 0.0182(2) Uani 1 1 d . . .
C12 C 0.39222(18) 0.66991(11) 0.48287(11) 0.0242(3) Uani 1 1 d . . .
C13 C 0.3766(2) 0.75463(12) 0.54459(13) 0.0300(3) Uani 1 1 d . . .
C14 C 0.46172(19) 0.76047(11) 0.62970(11) 0.0268(3) Uani 1 1 d . . .
C15 C 0.5636(2) 0.68057(13) 0.65393(11) 0.0280(3) Uani 1 1 d . . .
C16 C 0.58148(18) 0.59683(12) 0.59266(11) 0.0257(3) Uani 1 1 d . . .
H1 H 0.198(2) 0.3023(14) 0.4417(13) 0.019(4) Uiso 1 1 d . . .
H2 H 0.203(2) 0.3433(13) 0.2874(12) 0.016(4) Uiso 1 1 d . . .
H5 H 0.637(2) 0.4800(14) 0.4520(13) 0.024(4) Uiso 1 1 d . . .
H6A H 0.472(2) 0.2432(16) 0.3690(15) 0.034(5) Uiso 1 1 d . . .
H6B H 0.633(2) 0.3041(14) 0.3798(14) 0.024(4) Uiso 1 1 d . . .
H7A H 0.142(3) 0.5273(16) 0.3164(15) 0.032(5) Uiso 1 1 d . . .
H7B H 0.209(3) 0.5028(19) 0.2153(17) 0.045(6) Uiso 1 1 d . . .
H8A H 0.113(2) 0.4221(15) 0.5556(15) 0.031(5) Uiso 1 1 d . . .
H8B H 0.129(3) 0.5151(17) 0.4737(16) 0.045(6) Uiso 1 1 d . . .
H9A H 0.599(3) 0.3520(15) 0.1841(14) 0.031(5) Uiso 1 1 d . . .
H9B H 0.437(3) 0.402(2) 0.152(2) 0.066(8) Uiso 1 1 d . . .
H9C H 0.436(3) 0.2858(17) 0.1823(15) 0.042(6) Uiso 1 1 d . . .
H10A H 0.748(3) 0.4894(18) 0.2963(15) 0.034(5) Uiso 1 1 d . . .
H10B H 0.633(3) 0.5407(18) 0.2126(17) 0.047(6) Uiso 1 1 d . . .
H10C H 0.675(3) 0.6050(17) 0.3075(15) 0.036(5) Uiso 1 1 d . . .
H12 H 0.654(2) 0.5417(15) 0.6104(15) 0.032(5) Uiso 1 1 d . . .
H13 H 0.304(3) 0.808(2) 0.5253(18) 0.057(7) Uiso 1 1 d . . .
H14 H 0.444(2) 0.8189(17) 0.6694(14) 0.033(5) Uiso 1 1 d . . .
H15 H 0.620(2) 0.6831(15) 0.7149(14) 0.027(5) Uiso 1 1 d . . .
H16 H 0.333(2) 0.6695(15) 0.4292(14) 0.028(5) Uiso 1 1 d . . .
H17 H -0.060(3) 0.362(2) 0.4326(18) 0.053(7) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 P1 1.9508(8) . ?
P1 C6 1.8102(15) . ?
P1 C1 1.8141(18) . ?
P1 C5 1.8264(15) . ?
O1 C4 1.4296(19) . ?
O1 C7 1.431(2) . ?
O2 C8 1.429(2) . ?
O2 H17 0.85(2) . ?
C1 C8 1.522(2) . ?
C1 C2 1.554(2) . ?
C1 H1 1.009(18) . ?
C2 C7 1.513(2) . ?
C2 C3 1.557(2) . ?
C2 H2 0.958(17) . ?
C3 C9 1.520(2) . ?
C3 C6 1.539(2) . ?
C3 C4 1.570(2) . ?
C4 C10 1.520(2) . ?
C4 C5 1.5775(19) . ?
C5 C11 1.5172(19) . ?
C5 H5 0.952(19) . ?
C6 H6A 0.92(2) . ?
C6 H6B 0.982(19) . ?
C7 H7A 0.94(2) . ?
C7 H7B 0.97(2) . ?
C8 H8A 1.03(2) . ?
C8 H8B 0.97(2) . ?
C9 H9A 1.00(2) . ?
C9 H9B 0.97(3) . ?
C9 H9C 0.99(2) . ?
C10 H10A 1.06(2) . ?
C10 H10B 0.94(2) . ?
C10 H10C 0.99(2) . ?
C11 C12 1.390(2) . ?
C11 C16 1.400(2) . ?
C12 C13 1.395(2) . ?
C12 H16 0.89(2) . ?
C13 C14 1.378(2) . ?
C13 H13 0.96(3) . ?
C14 C15 1.384(2) . ?
C14 H14 0.95(2) . ?
C15 C16 1.383(2) . ?
C15 H15 0.965(19) . ?
C16 H12 0.97(2) . ?

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
C6 P1 C1 92.52(7) . . ?
C6 P1 C5 91.37(7) . . ?
C1 P1 C5 105.95(7) . . ?
C6 P1 S1 124.04(5) . . ?
C1 P1 S1 117.46(5) . . ?
C5 P1 S1 119.81(5) . . ?
C4 O1 C7 110.79(12) . . ?
C8 O2 H17 112.5(18) . . ?
C8 C1 C2 118.85(13) . . ?
C8 C1 P1 117.08(11) . . ?
C2 C1 P1 102.92(10) . . ?
C8 C1 H1 104.3(10) . . ?
C2 C1 H1 108.2(10) . . ?
P1 C1 H1 104.4(10) . . ?
C7 C2 C1 115.73(14) . . ?
C7 C2 C3 101.62(13) . . ?
C1 C2 C3 108.58(12) . . ?
C7 C2 H2 109.0(10) . . ?
C1 C2 H2 107.8(10) . . ?
C3 C2 H2 114.2(10) . . ?
C9 C3 C6 114.01(12) . . ?
C9 C3 C2 112.26(13) . . ?
C6 C3 C2 107.13(12) . . ?
C9 C3 C4 114.56(12) . . ?
C6 C3 C4 108.38(11) . . ?
C2 C3 C4 99.30(11) . . ?
O1 C4 C10 107.21(12) . . ?
O1 C4 C3 104.79(12) . . ?
C10 C4 C3 116.01(12) . . ?
O1 C4 C5 112.91(11) . . ?
C10 C4 C5 109.23(12) . . ?
C3 C4 C5 106.78(11) . . ?
C11 C5 C4 122.41(11) . . ?
C11 C5 P1 117.20(10) . . ?
C4 C5 P1 102.98(9) . . ?
C11 C5 H5 105.6(11) . . ?
C4 C5 H5 105.6(11) . . ?
P1 C5 H5 100.5(11) . . ?
C3 C6 P1 95.52(9) . . ?
C3 C6 H6A 110.0(13) . . ?
P1 C6 H6A 112.5(13) . . ?
C3 C6 H6B 115.5(11) . . ?
P1 C6 H6B 111.4(11) . . ?
H6A C6 H6B 111.2(17) . . ?
O1 C7 C2 106.50(13) . . ?
O1 C7 H7A 111.8(13) . . ?
C2 C7 H7A 110.4(12) . . ?
O1 C7 H7B 106.8(14) . . ?
C2 C7 H7B 114.4(15) . . ?
H7A C7 H7B 107.0(17) . . ?
O2 C8 C1 111.43(14) . . ?
O2 C8 H8A 108.5(12) . . ?
C1 C8 H8A 108.3(11) . . ?
O2 C8 H8B 102.4(14) . . ?
C1 C8 H8B 113.7(14) . . ?
H8A C8 H8B 112.3(17) . . ?
C3 C9 H9A 111.8(12) . . ?
C3 C9 H9B 112.0(16) . . ?
H9A C9 H9B 106(2) . . ?
C3 C9 H9C 110.4(13) . . ?
H9A C9 H9C 109.8(18) . . ?
H9B C9 H9C 106(2) . . ?
C4 C10 H10A 110.6(12) . . ?
C4 C10 H10B 111.1(15) . . ?
H10A C10 H10B 110.6(18) . . ?
C4 C10 H10C 108.6(12) . . ?
H10A C10 H10C 104.9(17) . . ?
H10B C10 H10C 110.9(19) . . ?
C12 C11 C16 118.03(13) . . ?
C12 C11 C5 125.40(12) . . ?
C16 C11 C5 116.57(12) . . ?
C11 C12 C13 120.37(14) . . ?
C11 C12 H16 122.3(13) . . ?
C13 C12 H16 117.3(13) . . ?
C14 C13 C12 120.97(15) . . ?
C14 C13 H13 121.7(16) . . ?
C12 C13 H13 117.3(16) . . ?
C13 C14 C15 119.11(14) . . ?
C13 C14 H14 117.2(12) . . ?
C15 C14 H14 123.6(12) . . ?
C16 C15 C14 120.39(14) . . ?
C16 C15 H15 120.4(12) . . ?
C14 C15 H15 119.2(12) . . ?
C15 C16 C11 121.10(14) . . ?
C15 C16 H12 119.4(12) . . ?
C11 C16 H12 119.5(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 P1 C1 C8 -169.21(12) . . . . ?
C5 P1 C1 C8 -77.07(13) . . . . ?
S1 P1 C1 C8 59.92(13) . . . . ?
C6 P1 C1 C2 -36.89(11) . . . . ?
C5 P1 C1 C2 55.26(11) . . . . ?
S1 P1 C1 C2 -167.75(8) . . . . ?
C8 C1 C2 C7 26.8(2) . . . . ?
P1 C1 C2 C7 -104.46(13) . . . . ?
C8 C1 C2 C3 140.27(13) . . . . ?
P1 C1 C2 C3 8.99(14) . . . . ?
C7 C2 C3 C9 -81.75(15) . . . . ?
C1 C2 C3 C9 155.80(12) . . . . ?
C7 C2 C3 C6 152.37(12) . . . . ?
C1 C2 C3 C6 29.91(16) . . . . ?
C7 C2 C3 C4 39.73(14) . . . . ?
C1 C2 C3 C4 -82.73(13) . . . . ?
C7 O1 C4 C10 140.18(13) . . . . ?
C7 O1 C4 C3 16.36(16) . . . . ?
C7 O1 C4 C5 -99.47(14) . . . . ?
C9 C3 C4 O1 84.97(16) . . . . ?
C6 C3 C4 O1 -146.47(12) . . . . ?
C2 C3 C4 O1 -34.82(13) . . . . ?
C9 C3 C4 C10 -33.01(19) . . . . ?
C6 C3 C4 C10 95.55(15) . . . . ?
C2 C3 C4 C10 -152.81(13) . . . . ?
C9 C3 C4 C5 -155.01(13) . . . . ?
C6 C3 C4 C5 -26.45(15) . . . . ?
C2 C3 C4 C5 85.19(12) . . . . ?
O1 C4 C5 C11 -33.37(18) . . . . ?
C10 C4 C5 C11 85.81(16) . . . . ?
C3 C4 C5 C11 -148.01(12) . . . . ?
O1 C4 C5 P1 101.21(12) . . . . ?
C10 C4 C5 P1 -139.61(10) . . . . ?
C3 C4 C5 P1 -13.43(12) . . . . ?
C6 P1 C5 C11 178.06(11) . . . . ?
C1 P1 C5 C11 85.05(11) . . . . ?
S1 P1 C5 C11 -50.72(12) . . . . ?
C6 P1 C5 C4 40.60(10) . . . . ?
C1 P1 C5 C4 -52.41(10) . . . . ?
S1 P1 C5 C4 171.81(7) . . . . ?
C9 C3 C6 P1 -178.05(12) . . . . ?
C2 C3 C6 P1 -53.22(12) . . . . ?
C4 C3 C6 P1 53.08(12) . . . . ?
C1 P1 C6 C3 52.23(10) . . . . ?
C5 P1 C6 C3 -53.81(10) . . . . ?
S1 P1 C6 C3 178.15(7) . . . . ?
C4 O1 C7 C2 10.12(18) . . . . ?
C1 C2 C7 O1 85.21(16) . . . . ?
C3 C2 C7 O1 -32.19(16) . . . . ?
C2 C1 C8 O2 62.82(18) . . . . ?
P1 C1 C8 O2 -172.53(11) . . . . ?
C4 C5 C11 C12 25.0(2) . . . . ?
P1 C5 C11 C12 -103.72(15) . . . . ?
C4 C5 C11 C16 -155.15(13) . . . . ?
P1 C5 C11 C16 76.15(15) . . . . ?
C16 C11 C12 C13 1.8(2) . . . . ?
C5 C11 C12 C13 -178.28(14) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C16 1.1(2) . . . . ?
C14 C15 C16 C11 -0.4(2) . . . . ?
C12 C11 C16 C15 -1.0(2) . . . . ?
C5 C11 C16 C15 179.08(14) . . . . ?
####################################################################### 
# 
# 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_x1781
_database_code_depnum_ccdc_archive 'CCDC 989752'
_audit_update_record             
;
2014-03-03 deposited with the CCDC.
2015-07-30 downloaded from the CCDC.
;

_audit_creation_date             2014-01-25T14:25:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C16 H21 O2 P S'
_chemical_formula_weight         308.36
_chemical_absolute_configuration rmad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.123(5)
_cell_length_b                   11.681(5)
_cell_length_c                   14.355(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_volume                     1529.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    10205
_cell_measurement_theta_min      3.478
_cell_measurement_theta_max      32.277

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.99838
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.356
_diffrn_orient_matrix_ub_11      0.0217093
_diffrn_orient_matrix_ub_12      0.0110907
_diffrn_orient_matrix_ub_13      0.0465707
_diffrn_orient_matrix_ub_21      -0.0345472
_diffrn_orient_matrix_ub_22      -0.0513632
_diffrn_orient_matrix_ub_23      0.0146241
_diffrn_orient_matrix_ub_31      0.0661616
_diffrn_orient_matrix_ub_32      -0.0304583
_diffrn_orient_matrix_ub_33      -0.007674
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_number            20682
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4660
_reflns_number_gt                4410
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SIR92 (Giacovazzo 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 for Windows (L. J. Farrugia, 1997)'
_computing_publication_material  'WINGX  (L.J. 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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0318P)²+0.2944P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4660
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(5)
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   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
S S 0.1246 0.1234 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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 0.89793(4) 0.56148(3) 0.54941(3) 0.02788(8) Uani 1 1 d . . .
P1 P 0.72709(3) 0.52822(3) 0.47331(2) 0.01751(7) Uani 1 1 d . . .
O2 O 0.68751(12) 0.26071(9) 0.50325(7) 0.0275(2) Uani 1 1 d . . .
01 O 0.37653(10) 0.40354(7) 0.42189(7) 0.01871(18) Uani 1 1 d . . .
C1 C 0.73783(15) 0.41031(11) 0.39008(9) 0.0203(2) Uani 1 1 d . . .
C2 C 0.59495(15) 0.42326(11) 0.33190(9) 0.0192(2) Uani 1 1 d . . .
C3 C 0.52964(14) 0.54391(10) 0.35322(8) 0.0173(2) Uani 1 1 d . . .
C4 C 0.43762(13) 0.51477(9) 0.44186(8) 0.0155(2) Uani 1 1 d . . .
C5 C 0.54707(13) 0.50426(9) 0.52757(9) 0.0151(2) Uani 1 1 d . . .
C6 C 0.65466(15) 0.62308(11) 0.38381(10) 0.0204(3) Uani 1 1 d . . .
C7 C 0.46862(16) 0.34346(11) 0.35610(10) 0.0210(3) Uani 1 1 d . . .
C8 C 0.77986(17) 0.29308(12) 0.42784(10) 0.0249(3) Uani 1 1 d . . .
C9 C 0.44034(17) 0.59081(12) 0.27223(10) 0.0241(3) Uani 1 1 d . . .
C10 C 0.30970(14) 0.59366(11) 0.46106(10) 0.0206(2) Uani 1 1 d . . .
C11 C 0.51487(13) 0.57942(10) 0.61017(8) 0.0159(2) Uani 1 1 d . . .
C12 C 0.44379(15) 0.53326(11) 0.68699(9) 0.0201(2) Uani 1 1 d . . .
C13 C 0.40613(16) 0.60049(12) 0.76357(10) 0.0230(3) Uani 1 1 d . . .
C14 C 0.43847(15) 0.71603(12) 0.76374(9) 0.0217(3) Uani 1 1 d . . .
C15 C 0.50954(16) 0.76358(11) 0.68795(10) 0.0242(3) Uani 1 1 d . . .
C16 C 0.54793(17) 0.69628(11) 0.61198(10) 0.0225(3) Uani 1 1 d . . .
H1 H 0.8221(19) 0.4357(15) 0.3528(11) 0.024(4) Uiso 1 1 d . . .
H2 H 0.617(2) 0.4144(15) 0.2689(13) 0.026(4) Uiso 1 1 d . . .
H6A H 0.7314(19) 0.6384(14) 0.3331(12) 0.025(4) Uiso 1 1 d . . .
H6B H 0.617(2) 0.6985(16) 0.4064(13) 0.031(5) Uiso 1 1 d . . .
H8A H 0.768(2) 0.2379(14) 0.3787(11) 0.023(4) Uiso 1 1 d . . .
H8B H 0.885(2) 0.2977(14) 0.4505(12) 0.025(4) Uiso 1 1 d . . .
H7A H 0.4134(16) 0.3275(12) 0.2992(11) 0.014(4) Uiso 1 1 d . . .
H9A H 0.504(2) 0.5984(15) 0.2185(13) 0.030(5) Uiso 1 1 d . . .
H9B H 0.364(2) 0.5414(17) 0.2545(13) 0.032(5) Uiso 1 1 d . . .
H9C H 0.4007(19) 0.6642(15) 0.2857(12) 0.027(4) Uiso 1 1 d . . .
H10A H 0.3421(17) 0.6715(13) 0.4686(11) 0.017(4) Uiso 1 1 d . . .
H10B H 0.242(2) 0.5870(15) 0.4113(13) 0.030(5) Uiso 1 1 d . . .
H10C H 0.258(2) 0.5658(16) 0.5157(14) 0.037(5) Uiso 1 1 d . . .
H12 H 0.4162(18) 0.4535(15) 0.6872(11) 0.026(4) Uiso 1 1 d . . .
H13 H 0.356(2) 0.5656(16) 0.8124(14) 0.035(5) Uiso 1 1 d . . .
H14 H 0.4092(19) 0.7655(14) 0.8170(13) 0.027(4) Uiso 1 1 d . . .
H15 H 0.531(2) 0.8496(17) 0.6842(14) 0.037(5) Uiso 1 1 d . . .
H16 H 0.600(2) 0.7308(15) 0.5609(13) 0.032(5) Uiso 1 1 d . . .
H17 H 0.726(2) 0.2047(18) 0.5286(14) 0.043(5) Uiso 1 1 d . . .
H5 H 0.5461(18) 0.4255(14) 0.5442(11) 0.022(4) Uiso 1 1 d . . .
H7B H 0.499(2) 0.2696(15) 0.3830(12) 0.026(4) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 P1 1.9425(9) . ?
P1 C6 1.8208(14) . ?
P1 C1 1.8260(14) . ?
P1 C5 1.8391(15) . ?
O2 C8 1.4230(18) . ?
O2 H17 0.83(2) . ?
01 C4 1.4424(14) . ?
01 C7 1.4458(16) . ?
C1 C8 1.5218(18) . ?
C1 C2 1.555(2) . ?
C1 H1 0.982(17) . ?
C2 C7 1.522(2) . ?
C2 C3 1.5604(18) . ?
C2 H2 0.931(18) . ?
C3 C9 1.5217(18) . ?
C3 C6 1.5326(19) . ?
C3 C4 1.5620(17) . ?
C4 C10 1.5123(18) . ?
C4 C5 1.5894(17) . ?
C5 C11 1.5044(17) . ?
C5 H5 0.950(16) . ?
C6 H6A 1.026(18) . ?
C6 H6B 1.000(19) . ?
C7 H7A 0.977(15) . ?
C7 H7B 0.984(17) . ?
C8 H8A 0.962(17) . ?
C8 H8B 1.010(18) . ?
C9 H9A 0.972(19) . ?
C9 H9B 0.939(19) . ?
C9 H9C 0.950(17) . ?
C10 H10A 0.962(15) . ?
C10 H10B 0.948(19) . ?
C10 H10C 0.97(2) . ?
C11 C12 1.3883(17) . ?
C11 C16 1.3982(18) . ?
C12 C13 1.3940(19) . ?
C12 H12 0.965(17) . ?
C13 C14 1.381(2) . ?
C13 H13 0.93(2) . ?
C14 C15 1.383(2) . ?
C14 H14 0.995(18) . ?
C15 C16 1.3892(19) . ?
C15 H15 1.02(2) . ?
C16 H16 0.964(19) . ?

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
C6 P1 C1 90.96(7) . . ?
C6 P1 C5 93.86(6) . . ?
C1 P1 C5 102.14(6) . . ?
C6 P1 S1 124.49(5) . . ?
C1 P1 S1 118.41(5) . . ?
C5 P1 S1 120.58(5) . . ?
C8 O2 H17 107.0(14) . . ?
C4 01 C7 110.03(10) . . ?
C8 C1 C2 119.33(12) . . ?
C8 C1 P1 117.34(10) . . ?
C2 C1 P1 103.47(8) . . ?
C8 C1 H1 105.6(10) . . ?
C2 C1 H1 109.5(10) . . ?
P1 C1 H1 99.8(10) . . ?
C7 C2 C1 116.89(11) . . ?
C7 C2 C3 102.66(10) . . ?
C1 C2 C3 107.61(10) . . ?
C7 C2 H2 108.4(11) . . ?
C1 C2 H2 109.3(11) . . ?
C3 C2 H2 111.9(11) . . ?
C9 C3 C6 113.58(11) . . ?
C9 C3 C2 112.31(11) . . ?
C6 C3 C2 108.48(11) . . ?
C9 C3 C4 114.40(11) . . ?
C6 C3 C4 107.35(10) . . ?
C2 C3 C4 99.68(9) . . ?
01 C4 C10 106.67(10) . . ?
01 C4 C3 104.01(9) . . ?
C10 C4 C3 115.49(10) . . ?
01 C4 C5 109.09(9) . . ?
C10 C4 C5 113.01(10) . . ?
C3 C4 C5 108.05(10) . . ?
C11 C5 C4 116.26(10) . . ?
C11 C5 P1 114.80(8) . . ?
C4 C5 P1 102.79(8) . . ?
C11 C5 H5 111.4(10) . . ?
C4 C5 H5 105.3(10) . . ?
P1 C5 H5 105.2(10) . . ?
C3 C6 P1 96.03(8) . . ?
C3 C6 H6A 114.2(10) . . ?
P1 C6 H6A 111.0(10) . . ?
C3 C6 H6B 111.5(11) . . ?
P1 C6 H6B 115.6(11) . . ?
H6A C6 H6B 108.3(14) . . ?
01 C7 C2 106.96(10) . . ?
01 C7 H7A 109.8(9) . . ?
C2 C7 H7A 108.4(9) . . ?
01 C7 H7B 109.3(10) . . ?
C2 C7 H7B 114.6(11) . . ?
H7A C7 H7B 107.7(13) . . ?
O2 C8 C1 111.16(11) . . ?
O2 C8 H8A 108.3(10) . . ?
C1 C8 H8A 108.2(10) . . ?
O2 C8 H8B 109.2(10) . . ?
C1 C8 H8B 107.7(10) . . ?
H8A C8 H8B 112.2(15) . . ?
C3 C9 H9A 108.5(11) . . ?
C3 C9 H9B 112.5(11) . . ?
H9A C9 H9B 106.6(15) . . ?
C3 C9 H9C 111.9(11) . . ?
H9A C9 H9C 107.9(14) . . ?
H9B C9 H9C 109.1(15) . . ?
C4 C10 H10A 111.0(9) . . ?
C4 C10 H10B 108.4(11) . . ?
H10A C10 H10B 111.3(14) . . ?
C4 C10 H10C 108.5(11) . . ?
H10A C10 H10C 112.0(15) . . ?
H10B C10 H10C 105.4(15) . . ?
C12 C11 C16 117.72(12) . . ?
C12 C11 C5 119.38(11) . . ?
C16 C11 C5 122.84(11) . . ?
C11 C12 C13 121.51(12) . . ?
C11 C12 H12 119.9(10) . . ?
C13 C12 H12 118.5(10) . . ?
C14 C13 C12 119.94(13) . . ?
C14 C13 H13 122.1(12) . . ?
C12 C13 H13 117.9(12) . . ?
C13 C14 C15 119.41(12) . . ?
C13 C14 H14 120.8(10) . . ?
C15 C14 H14 119.8(10) . . ?
C14 C15 C16 120.56(13) . . ?
C14 C15 H15 121.5(11) . . ?
C16 C15 H15 117.8(11) . . ?
C15 C16 C11 120.84(13) . . ?
C15 C16 H16 119.1(11) . . ?
C11 C16 H16 120.1(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 P1 C1 C8 -173.59(11) . . . . ?
C5 P1 C1 C8 -79.43(12) . . . . ?
S1 P1 C1 C8 55.64(12) . . . . ?
C6 P1 C1 C2 -39.89(9) . . . . ?
C5 P1 C1 C2 54.28(9) . . . . ?
S1 P1 C1 C2 -170.66(7) . . . . ?
C8 C1 C2 C7 31.48(16) . . . . ?
P1 C1 C2 C7 -101.07(11) . . . . ?
C8 C1 C2 C3 146.24(11) . . . . ?
P1 C1 C2 C3 13.69(11) . . . . ?
C7 C2 C3 C9 -84.04(13) . . . . ?
C1 C2 C3 C9 152.07(11) . . . . ?
C7 C2 C3 C6 149.58(10) . . . . ?
C1 C2 C3 C6 25.68(13) . . . . ?
C7 C2 C3 C4 37.50(12) . . . . ?
C1 C2 C3 C4 -86.40(11) . . . . ?
C7 01 C4 C10 148.20(11) . . . . ?
C7 01 C4 C3 25.67(12) . . . . ?
C7 01 C4 C5 -89.43(12) . . . . ?
C9 C3 C4 01 81.25(12) . . . . ?
C6 C3 C4 01 -151.74(9) . . . . ?
C2 C3 C4 01 -38.77(11) . . . . ?
C9 C3 C4 C10 -35.28(15) . . . . ?
C6 C3 C4 C10 91.73(12) . . . . ?
C2 C3 C4 C10 -155.30(10) . . . . ?
C9 C3 C4 C5 -162.92(10) . . . . ?
C6 C3 C4 C5 -35.91(12) . . . . ?
C2 C3 C4 C5 77.06(10) . . . . ?
01 C4 C5 C11 -123.05(11) . . . . ?
C10 C4 C5 C11 -4.57(14) . . . . ?
C3 C4 C5 C11 124.48(11) . . . . ?
01 C4 C5 P1 110.68(8) . . . . ?
C10 C4 C5 P1 -130.84(9) . . . . ?
C3 C4 C5 P1 -1.78(10) . . . . ?
C6 P1 C5 C11 -96.46(10) . . . . ?
C1 P1 C5 C11 171.73(8) . . . . ?
S1 P1 C5 C11 37.91(10) . . . . ?
C6 P1 C5 C4 30.74(8) . . . . ?
C1 P1 C5 C4 -61.07(8) . . . . ?
S1 P1 C5 C4 165.11(5) . . . . ?
C9 C3 C6 P1 -177.46(10) . . . . ?
C2 C3 C6 P1 -51.81(10) . . . . ?
C4 C3 C6 P1 55.05(10) . . . . ?
C1 P1 C6 C3 52.56(9) . . . . ?
C5 P1 C6 C3 -49.67(9) . . . . ?
S1 P1 C6 C3 178.64(6) . . . . ?
C4 01 C7 C2 -0.96(13) . . . . ?
C1 C2 C7 01 93.46(13) . . . . ?
C3 C2 C7 01 -24.03(13) . . . . ?
C2 C1 C8 O2 -72.93(16) . . . . ?
P1 C1 C8 O2 53.32(15) . . . . ?
C4 C5 C11 C12 99.91(13) . . . . ?
P1 C5 C11 C12 -140.10(10) . . . . ?
C4 C5 C11 C16 -77.32(15) . . . . ?
P1 C5 C11 C16 42.67(15) . . . . ?
C16 C11 C12 C13 0.1(2) . . . . ?
C5 C11 C12 C13 -177.30(12) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 C11 0.4(2) . . . . ?
C12 C11 C16 C15 -0.5(2) . . . . ?
C5 C11 C16 C15 176.74(13) . . . . ?
####################################################################### 
# 
# 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_c2
_database_code_depnum_ccdc_archive 'CCDC 989753'
_audit_update_record             
;
2014-03-03 deposited with the CCDC.
2015-07-30 downloaded from the CCDC.
;

_audit_creation_date             2014-01-27T14:22:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C22 H26 O2 P2 S2'
_chemical_formula_weight         448.49
_chemical_absolute_configuration rmad

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2
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'

_cell_length_a                   29.1990(10)
_cell_length_b                   9.1211(2)
_cell_length_c                   18.0309(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.228(3)
_cell_angle_gamma                90
_cell_volume                     4445.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    14660
_cell_measurement_theta_min      3.068
_cell_measurement_theta_max      30.332

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

_exptl_crystal_description       'thin needles'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.34
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.99659
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.356
_diffrn_orient_matrix_ub_11      0.0266864
_diffrn_orient_matrix_ub_12      0.0122938
_diffrn_orient_matrix_ub_13      -0.0144103
_diffrn_orient_matrix_ub_21      0.0305393
_diffrn_orient_matrix_ub_22      -0.0055671
_diffrn_orient_matrix_ub_23      0.0215952
_diffrn_orient_matrix_ub_31      0.0020609
_diffrn_orient_matrix_ub_32      -0.0766172
_diffrn_orient_matrix_ub_33      -0.003883
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.037
_diffrn_reflns_number            36663
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             11014
_reflns_number_gt                10127
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SIR92 (Giacovazzo 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 for Windows (L. J. Farrugia, 1997)'
_computing_publication_material  'WINGX  (L.J. 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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0311P)²+0.7319P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         11014
_refine_ls_number_parameters     713
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0.074
_refine_ls_shift/su_mean         0.009
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   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
S S 0.1246 0.1234 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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 0.739109(18) 0.99145(6) 0.58573(3) 0.02611(10) Uani 1 1 d . . .
S2 S 0.913673(19) 1.11357(5) 0.52782(3) 0.02481(11) Uani 1 1 d . . .
S3 S 0.75266(2) 0.05804(6) 0.12047(3) 0.03312(12) Uani 1 1 d . . .
S4 S 0.58980(2) 0.35660(6) -0.02213(3) 0.02981(12) Uani 1 1 d . . .
P1 P 0.717782(16) 0.99443(5) 0.46953(3) 0.01708(9) Uani 1 1 d . . .
P2 P 0.893811(17) 0.96087(5) 0.44736(3) 0.01671(10) Uani 1 1 d . . .
P3 P 0.778898(18) 0.25627(5) 0.13449(3) 0.02002(10) Uani 1 1 d . . .
P4 P 0.607329(17) 0.50780(5) 0.05877(3) 0.01812(10) Uani 1 1 d . . .
O1 O 0.67654(5) 0.82746(15) 0.27310(8) 0.0246(3) Uani 1 1 d . . .
O2 O 0.83580(4) 0.93473(15) 0.40373(7) 0.0214(3) Uani 1 1 d . . .
O3 O 0.81662(5) 0.58751(16) 0.24041(8) 0.0302(3) Uani 1 1 d . . .
O4 O 0.66530(5) 0.54201(14) 0.10151(8) 0.0239(3) Uani 1 1 d . . .
C5 C 0.67933(7) 0.8472(2) 0.41068(12) 0.0212(4) Uani 1 1 d . . .
C4 C 0.65735(7) 0.9073(2) 0.32295(11) 0.0203(4) Uani 1 1 d . . .
C3 C 0.67854(7) 1.0636(2) 0.32580(10) 0.0187(4) Uani 1 1 d . . .
C2 C 0.73240(7) 1.02426(19) 0.33502(10) 0.0180(4) Uani 1 1 d . . .
C1 C 0.76460(6) 1.0160(2) 0.42600(10) 0.0178(3) Uani 1 1 d . . .
C6 C 0.67986(7) 1.1353(2) 0.40384(11) 0.0192(4) Uani 1 1 d . . .
C7 C 0.72572(7) 0.8807(2) 0.28791(12) 0.0225(4) Uani 1 1 d . . .
C8 C 0.80621(7) 0.9071(2) 0.45166(11) 0.0206(4) Uani 1 1 d . . .
C9 C 0.60145(8) 0.8957(3) 0.28735(15) 0.0321(5) Uani 1 1 d . . .
C10 C 0.65274(9) 1.1542(3) 0.25115(13) 0.0299(5) Uani 1 1 d . . .
C11 C 0.91813(7) 0.78270(19) 0.48686(11) 0.0180(4) Uani 1 1 d . . .
C12 C 0.89277(8) 0.6563(2) 0.45199(12) 0.0247(4) Uani 1 1 d . . .
C13 C 0.91129(9) 0.5198(2) 0.48372(14) 0.0308(5) Uani 1 1 d . . .
C14 C 0.95527(9) 0.5101(3) 0.54919(14) 0.0356(5) Uani 1 1 d . . .
C15 C 0.98063(9) 0.6359(3) 0.58401(13) 0.0323(5) Uani 1 1 d . . .
C16 C 0.96223(8) 0.7730(2) 0.55337(12) 0.0231(4) Uani 1 1 d . . .
C17 C 0.90909(6) 0.9976(2) 0.36152(10) 0.0187(3) Uani 1 1 d . . .
C18 C 0.94777(8) 1.0909(2) 0.36886(13) 0.0275(4) Uani 1 1 d . . .
C19 C 0.96052(8) 1.1184(3) 0.30307(14) 0.0338(5) Uani 1 1 d . . .
C20 C 0.93407(9) 1.0539(3) 0.23068(13) 0.0341(5) Uani 1 1 d . . .
C21 C 0.89511(10) 0.9626(3) 0.22247(13) 0.0367(5) Uani 1 1 d . . .
C22 C 0.88273(9) 0.9309(2) 0.28785(13) 0.0305(5) Uani 1 1 d . . .
C23 C 0.73522(7) 0.4080(2) 0.09735(11) 0.0191(4) Uani 1 1 d . . .
C24 C 0.76953(7) 0.54210(19) 0.10320(11) 0.0194(4) Uani 1 1 d . . .
C25 C 0.82288(6) 0.4834(2) 0.12308(11) 0.0213(4) Uani 1 1 d . . .
C26 C 0.83984(7) 0.4683(2) 0.21561(11) 0.0240(4) Uani 1 1 d . . .
C27 C 0.81902(8) 0.3202(2) 0.23264(12) 0.0248(4) Uani 1 1 d . . .
C28 C 0.81922(8) 0.3286(2) 0.08815(13) 0.0256(4) Uani 1 1 d . . .
C29 C 0.85355(9) 0.5890(3) 0.09544(16) 0.0339(5) Uani 1 1 d . . .
C30 C 0.89524(8) 0.4803(3) 0.26209(14) 0.0377(5) Uani 1 1 d . . .
C31 C 0.77712(8) 0.6459(2) 0.17240(13) 0.0276(4) Uani 1 1 d . . .
C32 C 0.69875(7) 0.4208(2) 0.13755(13) 0.0256(4) Uani 1 1 d . . .
C33 C 0.58809(7) 0.4661(2) 0.14047(11) 0.0205(4) Uani 1 1 d . . .
C34 C 0.61364(9) 0.5244(2) 0.21577(13) 0.0303(5) Uani 1 1 d . . .
C35 C 0.59884(10) 0.4934(3) 0.27862(14) 0.0406(6) Uani 1 1 d . . .
C36 C 0.55823(10) 0.4074(3) 0.26566(16) 0.0442(7) Uani 1 1 d . . .
C37 C 0.53186(9) 0.3496(3) 0.19066(16) 0.0428(6) Uani 1 1 d . . .
C38 C 0.54723(8) 0.3771(2) 0.12800(13) 0.0293(5) Uani 1 1 d . . .
C39 C 0.58440(7) 0.6875(2) 0.02225(11) 0.0200(4) Uani 1 1 d . . .
C40 C 0.60666(8) 0.8146(2) 0.06393(12) 0.0259(4) Uani 1 1 d . . .
C41 C 0.58729(9) 0.9497(2) 0.03388(13) 0.0308(5) Uani 1 1 d . . .
C42 C 0.54606(8) 0.9607(2) -0.03637(13) 0.0307(5) Uani 1 1 d . . .
C43 C 0.52389(8) 0.8362(3) -0.07723(12) 0.0293(5) Uani 1 1 d . . .
C44 C 0.54284(7) 0.6995(2) -0.04816(12) 0.0236(4) Uani 1 1 d . . .
H5A H 0.6549(9) 0.820(3) 0.4301(13) 0.031(6) Uiso 1 1 d . . .
H5B H 0.6972(8) 0.765(2) 0.4156(13) 0.026(6) Uiso 1 1 d . . .
H2 H 0.7448(8) 1.092(2) 0.3133(12) 0.020(5) Uiso 1 1 d . . .
H1 H 0.7785(7) 1.108(2) 0.4433(11) 0.011(5) Uiso 1 1 d . . .
H6A H 0.6942(7) 1.227(2) 0.4095(11) 0.012(5) Uiso 1 1 d . . .
H6B H 0.6468(9) 1.145(3) 0.4058(13) 0.032(6) Uiso 1 1 d . . .
H7A H 0.7463(8) 0.805(2) 0.3152(12) 0.018(5) Uiso 1 1 d . . .
H7B H 0.7254(8) 0.901(2) 0.2351(13) 0.026(5) Uiso 1 1 d . . .
H8A H 0.8281(7) 0.921(2) 0.5089(12) 0.016(5) Uiso 1 1 d . . .
H8B H 0.7951(8) 0.803(2) 0.4453(12) 0.023(5) Uiso 1 1 d . . .
H9A H 0.5871(10) 0.960(3) 0.3152(15) 0.052(8) Uiso 1 1 d . . .
H9B H 0.5886(9) 0.926(3) 0.2359(16) 0.044(7) Uiso 1 1 d . . .
H9C H 0.5928(10) 0.798(3) 0.2952(15) 0.047(7) Uiso 1 1 d . . .
H10A H 0.6179(9) 1.172(3) 0.2445(13) 0.035(6) Uiso 1 1 d . . .
H10B H 0.6699(9) 1.245(3) 0.2531(13) 0.032(6) Uiso 1 1 d . . .
H10C H 0.6527(8) 1.108(3) 0.2044(14) 0.034(6) Uiso 1 1 d . . .
H12 H 0.8640(9) 0.660(3) 0.4080(14) 0.034(6) Uiso 1 1 d . . .
H13 H 0.8955(8) 0.431(3) 0.4637(13) 0.029(6) Uiso 1 1 d . . .
H14 H 0.9654(8) 0.420(3) 0.5688(14) 0.031(6) Uiso 1 1 d . . .
H15 H 1.0110(9) 0.627(3) 0.6289(15) 0.041(7) Uiso 1 1 d . . .
H16 H 0.9794(8) 0.863(3) 0.5764(13) 0.032(6) Uiso 1 1 d . . .
H18 H 0.9642(9) 1.139(3) 0.4189(15) 0.046(8) Uiso 1 1 d . . .
H19 H 0.9869(9) 1.180(3) 0.3106(14) 0.038(7) Uiso 1 1 d . . .
H20 H 0.9419(8) 1.069(2) 0.1897(13) 0.030(6) Uiso 1 1 d . . .
H21 H 0.8781(8) 0.913(3) 0.1718(14) 0.035(6) Uiso 1 1 d . . .
H22 H 0.8594(10) 0.867(3) 0.2835(15) 0.044(7) Uiso 1 1 d . . .
H23 H 0.7178(8) 0.386(2) 0.0411(13) 0.022(5) Uiso 1 1 d . . .
H24 H 0.7563(7) 0.592(2) 0.0510(11) 0.010(4) Uiso 1 1 d . . .
H27A H 0.8447(8) 0.248(3) 0.2524(13) 0.031(6) Uiso 1 1 d . . .
H27B H 0.8041(8) 0.333(2) 0.2691(13) 0.025(6) Uiso 1 1 d . . .
H28A H 0.8051(8) 0.330(2) 0.0329(13) 0.023(5) Uiso 1 1 d . . .
H28B H 0.8502(9) 0.280(2) 0.1041(13) 0.028(6) Uiso 1 1 d . . .
H29A H 0.8551(9) 0.677(3) 0.1201(15) 0.039(7) Uiso 1 1 d . . .
H29B H 0.8891(10) 0.556(3) 0.1154(15) 0.051(8) Uiso 1 1 d . . .
H29C H 0.8401(8) 0.596(3) 0.0387(14) 0.032(6) Uiso 1 1 d . . .
H30A H 0.9028(9) 0.464(3) 0.3193(15) 0.046(7) Uiso 1 1 d . . .
H30B H 0.9071(8) 0.581(3) 0.2570(13) 0.029(6) Uiso 1 1 d . . .
H30C H 0.9150(9) 0.404(3) 0.2429(14) 0.038(7) Uiso 1 1 d . . .
H31 H 0.6383(9) 0.585(3) 0.2201(13) 0.031(6) Uiso 1 1 d . . .
H31A H 0.7866(8) 0.737(3) 0.1601(13) 0.034(6) Uiso 1 1 d . . .
H31B H 0.7488(10) 0.656(3) 0.1844(14) 0.039(7) Uiso 1 1 d . . .
H32A H 0.7132(7) 0.438(2) 0.1934(12) 0.013(5) Uiso 1 1 d . . .
H32B H 0.6811(8) 0.331(3) 0.1329(13) 0.031(6) Uiso 1 1 d . . .
H35 H 0.6194(9) 0.532(3) 0.3310(15) 0.047(7) Uiso 1 1 d . . .
H36 H 0.5456(10) 0.389(3) 0.3053(16) 0.051(8) Uiso 1 1 d . . .
H37 H 0.5024(10) 0.289(3) 0.1828(16) 0.052(8) Uiso 1 1 d . . .
H38 H 0.5307(9) 0.329(3) 0.0766(14) 0.036(6) Uiso 1 1 d . . .
H40 H 0.6358(8) 0.801(2) 0.1157(13) 0.028(6) Uiso 1 1 d . . .
H41 H 0.6011(8) 1.032(3) 0.0615(12) 0.027(6) Uiso 1 1 d . . .
H42 H 0.5329(9) 1.053(3) -0.0571(13) 0.034(6) Uiso 1 1 d . . .
H43 H 0.4955(10) 0.838(3) -0.1300(15) 0.046(7) Uiso 1 1 d . . .
H44 H 0.5278(8) 0.615(3) -0.0749(13) 0.031(6) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 P1 1.9471(6) . ?
S2 P2 1.9350(6) . ?
S3 P3 1.9426(7) . ?
S4 P4 1.9306(7) . ?
P1 C6 1.8130(19) . ?
P1 C5 1.813(2) . ?
P1 C1 1.8263(18) . ?
P2 O2 1.5928(13) . ?
P2 C17 1.7969(17) . ?
P2 C11 1.8083(18) . ?
P3 C28 1.807(2) . ?
P3 C27 1.810(2) . ?
P3 C23 1.8290(19) . ?
P4 O4 1.6031(13) . ?
P4 C39 1.7985(19) . ?
P4 C33 1.8046(18) . ?
O1 C4 1.426(2) . ?
O1 C7 1.442(2) . ?
O2 C8 1.457(2) . ?
O3 C31 1.431(3) . ?
O3 C26 1.439(2) . ?
O4 C32 1.455(2) . ?
C5 C4 1.564(3) . ?
C5 H5A 0.94(2) . ?
C5 H5B 0.90(2) . ?
C4 C9 1.515(3) . ?
C4 C3 1.547(3) . ?
C3 C10 1.515(3) . ?
C3 C6 1.539(2) . ?
C3 C2 1.560(2) . ?
C2 C7 1.533(3) . ?
C2 C1 1.554(2) . ?
C2 H2 0.88(2) . ?
C1 C8 1.501(3) . ?
C1 H1 0.93(2) . ?
C6 H6A 0.92(2) . ?
C6 H6B 0.98(2) . ?
C7 H7A 0.93(2) . ?
C7 H7B 0.97(2) . ?
C8 H8A 0.996(19) . ?
C8 H8B 0.99(2) . ?
C9 H9A 0.97(3) . ?
C9 H9B 0.90(3) . ?
C9 H9C 0.95(3) . ?
C10 H10A 0.99(2) . ?
C10 H10B 0.96(2) . ?
C10 H10C 0.94(2) . ?
C11 C12 1.386(3) . ?
C11 C16 1.391(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.91(2) . ?
C13 C14 1.380(3) . ?
C13 H13 0.93(2) . ?
C14 C15 1.381(3) . ?
C14 H14 0.90(2) . ?
C15 C16 1.390(3) . ?
C15 H15 0.95(2) . ?
C16 H16 0.97(2) . ?
C17 C18 1.380(3) . ?
C17 C22 1.397(3) . ?
C18 C19 1.394(3) . ?
C18 H18 0.95(3) . ?
C19 C20 1.372(3) . ?
C19 H19 0.92(3) . ?
C20 C21 1.372(3) . ?
C20 H20 0.86(2) . ?
C21 C22 1.388(3) . ?
C21 H21 0.97(2) . ?
C22 H22 0.88(3) . ?
C23 C32 1.502(3) . ?
C23 C24 1.559(3) . ?
C23 H23 0.97(2) . ?
C24 C31 1.514(3) . ?
C24 C25 1.555(2) . ?
C24 H24 0.982(18) . ?
C25 C29 1.521(3) . ?
C25 C28 1.534(3) . ?
C25 C26 1.557(3) . ?
C26 C30 1.518(3) . ?
C26 C27 1.558(3) . ?
C27 H27A 0.96(2) . ?
C27 H27B 0.92(2) . ?
C28 H28A 0.92(2) . ?
C28 H28B 0.95(2) . ?
C29 H29A 0.91(3) . ?
C29 H29B 1.01(3) . ?
C29 H29C 0.95(2) . ?
C30 H30A 0.98(2) . ?
C30 H30B 0.99(2) . ?
C30 H30C 1.04(3) . ?
C31 H31A 0.93(3) . ?
C31 H31B 0.93(3) . ?
C32 H32A 0.947(19) . ?
C32 H32B 0.95(2) . ?
C33 C34 1.384(3) . ?
C33 C38 1.389(3) . ?
C34 C35 1.386(3) . ?
C34 H31 0.89(2) . ?
C35 C36 1.366(4) . ?
C35 H35 0.97(3) . ?
C36 C37 1.383(4) . ?
C36 H36 0.94(3) . ?
C37 C38 1.387(3) . ?
C37 H37 0.99(3) . ?
C38 H38 0.97(2) . ?
C39 C44 1.389(3) . ?
C39 C40 1.401(3) . ?
C40 C41 1.378(3) . ?
C40 H40 1.01(2) . ?
C41 C42 1.382(3) . ?
C41 H41 0.91(2) . ?
C42 C43 1.375(3) . ?
C42 H42 0.94(2) . ?
C43 C44 1.384(3) . ?
C43 H43 1.00(3) . ?
C44 H44 0.93(2) . ?

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
C6 P1 C5 93.01(9) . . ?
C6 P1 C1 90.82(9) . . ?
C5 P1 C1 103.10(9) . . ?
C6 P1 S1 125.49(7) . . ?
C5 P1 S1 119.63(7) . . ?
C1 P1 S1 118.51(6) . . ?
O2 P2 C17 99.60(8) . . ?
O2 P2 C11 104.23(8) . . ?
C17 P2 C11 108.55(8) . . ?
O2 P2 S2 116.05(6) . . ?
C17 P2 S2 114.21(7) . . ?
C11 P2 S2 112.95(6) . . ?
C28 P3 C27 92.32(10) . . ?
C28 P3 C23 92.32(9) . . ?
C27 P3 C23 102.57(9) . . ?
C28 P3 S3 125.01(7) . . ?
C27 P3 S3 120.32(7) . . ?
C23 P3 S3 118.09(7) . . ?
O4 P4 C39 100.24(8) . . ?
O4 P4 C33 104.29(8) . . ?
C39 P4 C33 107.65(8) . . ?
O4 P4 S4 115.61(6) . . ?
C39 P4 S4 114.76(7) . . ?
C33 P4 S4 113.00(7) . . ?
C4 O1 C7 108.21(13) . . ?
C8 O2 P2 119.44(11) . . ?
C31 O3 C26 109.67(14) . . ?
C32 O4 P4 118.37(12) . . ?
C4 C5 P1 104.98(12) . . ?
C4 C5 H5A 112.9(14) . . ?
P1 C5 H5A 111.4(14) . . ?
C4 C5 H5B 113.2(14) . . ?
P1 C5 H5B 110.7(14) . . ?
H5A C5 H5B 104(2) . . ?
O1 C4 C9 108.33(16) . . ?
O1 C4 C3 104.12(14) . . ?
C9 C4 C3 115.57(16) . . ?
O1 C4 C5 110.47(15) . . ?
C9 C4 C5 111.61(17) . . ?
C3 C4 C5 106.47(14) . . ?
C10 C3 C6 114.39(16) . . ?
C10 C3 C4 114.52(16) . . ?
C6 C3 C4 107.04(15) . . ?
C10 C3 C2 111.27(16) . . ?
C6 C3 C2 108.96(14) . . ?
C4 C3 C2 99.55(13) . . ?
C7 C2 C1 116.30(15) . . ?
C7 C2 C3 103.04(15) . . ?
C1 C2 C3 107.86(14) . . ?
C7 C2 H2 109.9(13) . . ?
C1 C2 H2 108.6(14) . . ?
C3 C2 H2 111.0(14) . . ?
C8 C1 C2 116.97(15) . . ?
C8 C1 P1 116.53(13) . . ?
C2 C1 P1 101.92(11) . . ?
C8 C1 H1 107.2(12) . . ?
C2 C1 H1 108.7(11) . . ?
P1 C1 H1 104.7(12) . . ?
C3 C6 P1 95.41(12) . . ?
C3 C6 H6A 109.8(12) . . ?
P1 C6 H6A 115.5(12) . . ?
C3 C6 H6B 112.8(13) . . ?
P1 C6 H6B 114.1(13) . . ?
H6A C6 H6B 108.8(18) . . ?
O1 C7 C2 107.43(15) . . ?
O1 C7 H7A 104.3(13) . . ?
C2 C7 H7A 115.0(12) . . ?
O1 C7 H7B 104.1(13) . . ?
C2 C7 H7B 109.6(13) . . ?
H7A C7 H7B 115.4(18) . . ?
O2 C8 C1 107.18(14) . . ?
O2 C8 H8A 107.4(11) . . ?
C1 C8 H8A 111.1(11) . . ?
O2 C8 H8B 109.8(12) . . ?
C1 C8 H8B 113.8(12) . . ?
H8A C8 H8B 107.4(16) . . ?
C4 C9 H9A 110.4(16) . . ?
C4 C9 H9B 112.2(16) . . ?
H9A C9 H9B 105(2) . . ?
C4 C9 H9C 108.0(16) . . ?
H9A C9 H9C 107(2) . . ?
H9B C9 H9C 114(2) . . ?
C3 C10 H10A 109.9(13) . . ?
C3 C10 H10B 111.1(14) . . ?
H10A C10 H10B 111.1(19) . . ?
C3 C10 H10C 112.4(14) . . ?
H10A C10 H10C 108.1(19) . . ?
H10B C10 H10C 104(2) . . ?
C12 C11 C16 119.96(18) . . ?
C12 C11 P2 120.41(15) . . ?
C16 C11 P2 119.62(15) . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 121.7(16) . . ?
C13 C12 H12 118.3(16) . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 116.1(14) . . ?
C12 C13 H13 123.9(14) . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 117.2(15) . . ?
C15 C14 H14 122.7(15) . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 118.7(16) . . ?
C16 C15 H15 120.9(16) . . ?
C15 C16 C11 119.5(2) . . ?
C15 C16 H16 122.0(13) . . ?
C11 C16 H16 118.5(13) . . ?
C18 C17 C22 119.73(18) . . ?
C18 C17 P2 119.54(15) . . ?
C22 C17 P2 120.72(15) . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 118.3(16) . . ?
C19 C18 H18 121.5(16) . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 122.7(15) . . ?
C18 C19 H19 117.5(15) . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 120.7(15) . . ?
C21 C20 H20 118.8(15) . . ?
C20 C21 C22 120.4(2) . . ?
C20 C21 H21 119.5(14) . . ?
C22 C21 H21 119.8(14) . . ?
C21 C22 C17 119.3(2) . . ?
C21 C22 H22 120.3(16) . . ?
C17 C22 H22 120.2(16) . . ?
C32 C23 C24 117.46(16) . . ?
C32 C23 P3 113.92(13) . . ?
C24 C23 P3 103.17(12) . . ?
C32 C23 H23 109.6(12) . . ?
C24 C23 H23 107.7(13) . . ?
P3 C23 H23 104.0(12) . . ?
C31 C24 C25 101.74(15) . . ?
C31 C24 C23 115.86(16) . . ?
C25 C24 C23 107.92(14) . . ?
C31 C24 H24 112.5(11) . . ?
C25 C24 H24 112.2(11) . . ?
C23 C24 H24 106.7(10) . . ?
C29 C25 C28 113.98(17) . . ?
C29 C25 C24 111.67(17) . . ?
C28 C25 C24 108.30(15) . . ?
C29 C25 C26 114.80(17) . . ?
C28 C25 C26 107.63(15) . . ?
C24 C25 C26 99.34(14) . . ?
O3 C26 C30 107.60(16) . . ?
O3 C26 C25 105.64(14) . . ?
C30 C26 C25 115.19(17) . . ?
O3 C26 C27 109.20(16) . . ?
C30 C26 C27 111.58(17) . . ?
C25 C26 C27 107.37(15) . . ?
C26 C27 P3 104.07(13) . . ?
C26 C27 H27A 110.9(14) . . ?
P3 C27 H27A 105.6(14) . . ?
C26 C27 H27B 110.9(14) . . ?
P3 C27 H27B 115.6(13) . . ?
H27A C27 H27B 109.6(19) . . ?
C25 C28 P3 95.90(12) . . ?
C25 C28 H28A 111.1(14) . . ?
P3 C28 H28A 113.7(13) . . ?
C25 C28 H28B 113.4(13) . . ?
P3 C28 H28B 113.7(13) . . ?
H28A C28 H28B 108.6(19) . . ?
C25 C29 H29A 109.0(16) . . ?
C25 C29 H29B 110.3(15) . . ?
H29A C29 H29B 104(2) . . ?
C25 C29 H29C 109.9(14) . . ?
H29A C29 H29C 113(2) . . ?
H29B C29 H29C 111(2) . . ?
C26 C30 H30A 109.8(15) . . ?
C26 C30 H30B 110.5(13) . . ?
H30A C30 H30B 107(2) . . ?
C26 C30 H30C 112.1(13) . . ?
H30A C30 H30C 108(2) . . ?
H30B C30 H30C 109.0(18) . . ?
O3 C31 C24 107.04(16) . . ?
O3 C31 H31A 108.8(14) . . ?
C24 C31 H31A 109.1(14) . . ?
O3 C31 H31B 109.6(15) . . ?
C24 C31 H31B 112.7(15) . . ?
H31A C31 H31B 109(2) . . ?
O4 C32 C23 108.79(15) . . ?
O4 C32 H32A 107.5(11) . . ?
C23 C32 H32A 114.6(12) . . ?
O4 C32 H32B 111.3(14) . . ?
C23 C32 H32B 110.5(14) . . ?
H32A C32 H32B 104.2(17) . . ?
C34 C33 C38 119.64(18) . . ?
C34 C33 P4 120.06(16) . . ?
C38 C33 P4 120.30(15) . . ?
C33 C34 C35 120.3(2) . . ?
C33 C34 H31 116.3(15) . . ?
C35 C34 H31 123.3(15) . . ?
C36 C35 C34 119.7(2) . . ?
C36 C35 H35 123.3(15) . . ?
C34 C35 H35 116.9(15) . . ?
C35 C36 C37 120.8(2) . . ?
C35 C36 H36 122.6(17) . . ?
C37 C36 H36 116.4(17) . . ?
C36 C37 C38 119.7(2) . . ?
C36 C37 H37 119.2(16) . . ?
C38 C37 H37 121.1(16) . . ?
C37 C38 C33 119.8(2) . . ?
C37 C38 H38 119.9(14) . . ?
C33 C38 H38 120.2(14) . . ?
C44 C39 C40 119.50(18) . . ?
C44 C39 P4 118.81(15) . . ?
C40 C39 P4 121.67(14) . . ?
C41 C40 C39 119.40(19) . . ?
C41 C40 H40 123.6(13) . . ?
C39 C40 H40 116.9(13) . . ?
C40 C41 C42 120.7(2) . . ?
C40 C41 H41 119.6(13) . . ?
C42 C41 H41 119.6(13) . . ?
C43 C42 C41 120.1(2) . . ?
C43 C42 H42 119.1(14) . . ?
C41 C42 H42 120.8(14) . . ?
C42 C43 C44 120.08(19) . . ?
C42 C43 H43 123.5(15) . . ?
C44 C43 H43 116.3(16) . . ?
C43 C44 C39 120.2(2) . . ?
C43 C44 H44 120.6(14) . . ?
C39 C44 H44 119.2(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 P2 O2 C8 -177.11(14) . . . . ?
C11 P2 O2 C8 70.82(15) . . . . ?
S2 P2 O2 C8 -54.04(14) . . . . ?
C39 P4 O4 C32 -177.70(13) . . . . ?
C33 P4 O4 C32 70.95(14) . . . . ?
S4 P4 O4 C32 -53.75(14) . . . . ?
C6 P1 C5 C4 29.66(13) . . . . ?
C1 P1 C5 C4 -61.88(14) . . . . ?
S1 P1 C5 C4 164.00(10) . . . . ?
C7 O1 C4 C9 158.98(17) . . . . ?
C7 O1 C4 C3 35.46(18) . . . . ?
C7 O1 C4 C5 -78.49(18) . . . . ?
P1 C5 C4 O1 112.94(14) . . . . ?
P1 C5 C4 C9 -126.47(15) . . . . ?
P1 C5 C4 C3 0.49(17) . . . . ?
O1 C4 C3 C10 76.84(18) . . . . ?
C9 C4 C3 C10 -41.8(2) . . . . ?
C5 C4 C3 C10 -166.39(17) . . . . ?
O1 C4 C3 C6 -155.24(14) . . . . ?
C9 C4 C3 C6 86.1(2) . . . . ?
C5 C4 C3 C6 -38.48(18) . . . . ?
O1 C4 C3 C2 -41.91(16) . . . . ?
C9 C4 C3 C2 -160.59(16) . . . . ?
C5 C4 C3 C2 74.85(16) . . . . ?
C10 C3 C2 C7 -88.46(18) . . . . ?
C6 C3 C2 C7 144.52(15) . . . . ?
C4 C3 C2 C7 32.68(16) . . . . ?
C10 C3 C2 C1 148.00(16) . . . . ?
C6 C3 C2 C1 20.98(19) . . . . ?
C4 C3 C2 C1 -90.86(16) . . . . ?
C7 C2 C1 C8 32.0(2) . . . . ?
C3 C2 C1 C8 147.12(15) . . . . ?
C7 C2 C1 P1 -96.24(16) . . . . ?
C3 C2 C1 P1 18.83(16) . . . . ?
C6 P1 C1 C8 -172.62(14) . . . . ?
C5 P1 C1 C8 -79.33(15) . . . . ?
S1 P1 C1 C8 55.42(15) . . . . ?
C6 P1 C1 C2 -44.05(12) . . . . ?
C5 P1 C1 C2 49.24(13) . . . . ?
S1 P1 C1 C2 -176.00(9) . . . . ?
C10 C3 C6 P1 -175.21(15) . . . . ?
C4 C3 C6 P1 56.80(14) . . . . ?
C2 C3 C6 P1 -49.98(15) . . . . ?
C5 P1 C6 C3 -49.14(12) . . . . ?
C1 P1 C6 C3 54.03(12) . . . . ?
S1 P1 C6 C3 -179.35(8) . . . . ?
C4 O1 C7 C2 -13.50(19) . . . . ?
C1 C2 C7 O1 104.15(17) . . . . ?
C3 C2 C7 O1 -13.61(18) . . . . ?
P2 O2 C8 C1 126.40(13) . . . . ?
C2 C1 C8 O2 53.1(2) . . . . ?
P1 C1 C8 O2 173.99(12) . . . . ?
O2 P2 C11 C12 24.79(17) . . . . ?
C17 P2 C11 C12 -80.66(17) . . . . ?
S2 P2 C11 C12 151.61(14) . . . . ?
O2 P2 C11 C16 -154.29(15) . . . . ?
C17 P2 C11 C16 100.26(16) . . . . ?
S2 P2 C11 C16 -27.46(17) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
P2 C11 C12 C13 -178.78(16) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
P2 C11 C16 C15 179.48(15) . . . . ?
O2 P2 C17 C18 149.14(16) . . . . ?
C11 P2 C17 C18 -102.22(17) . . . . ?
S2 P2 C17 C18 24.78(18) . . . . ?
O2 P2 C17 C22 -31.82(18) . . . . ?
C11 P2 C17 C22 76.82(18) . . . . ?
S2 P2 C17 C22 -156.18(15) . . . . ?
C22 C17 C18 C19 -0.1(3) . . . . ?
P2 C17 C18 C19 178.96(17) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C20 C21 C22 -1.7(4) . . . . ?
C20 C21 C22 C17 2.5(4) . . . . ?
C18 C17 C22 C21 -1.6(3) . . . . ?
P2 C17 C22 C21 179.39(17) . . . . ?
C28 P3 C23 C32 -165.26(15) . . . . ?
C27 P3 C23 C32 -72.36(16) . . . . ?
S3 P3 C23 C32 62.49(16) . . . . ?
C28 P3 C23 C24 -36.82(13) . . . . ?
C27 P3 C23 C24 56.08(14) . . . . ?
S3 P3 C23 C24 -169.07(9) . . . . ?
C32 C23 C24 C31 22.5(2) . . . . ?
P3 C23 C24 C31 -103.70(16) . . . . ?
C32 C23 C24 C25 135.74(16) . . . . ?
P3 C23 C24 C25 9.52(16) . . . . ?
C31 C24 C25 C29 -82.3(2) . . . . ?
C23 C24 C25 C29 155.30(17) . . . . ?
C31 C24 C25 C28 151.37(16) . . . . ?
C23 C24 C25 C28 29.00(19) . . . . ?
C31 C24 C25 C26 39.19(17) . . . . ?
C23 C24 C25 C26 -83.18(16) . . . . ?
C31 O3 C26 C30 140.18(18) . . . . ?
C31 O3 C26 C25 16.7(2) . . . . ?
C31 O3 C26 C27 -98.56(18) . . . . ?
C29 C25 C26 O3 84.4(2) . . . . ?
C28 C25 C26 O3 -147.50(15) . . . . ?
C24 C25 C26 O3 -34.78(17) . . . . ?
C29 C25 C26 C30 -34.1(2) . . . . ?
C28 C25 C26 C30 93.9(2) . . . . ?
C24 C25 C26 C30 -153.38(17) . . . . ?
C29 C25 C26 C27 -159.10(17) . . . . ?
C28 C25 C26 C27 -31.0(2) . . . . ?
C24 C25 C26 C27 81.67(17) . . . . ?
O3 C26 C27 P3 106.53(15) . . . . ?
C30 C26 C27 P3 -134.65(16) . . . . ?
C25 C26 C27 P3 -7.55(18) . . . . ?
C28 P3 C27 C26 35.56(14) . . . . ?
C23 P3 C27 C26 -57.34(15) . . . . ?
S3 P3 C27 C26 169.09(10) . . . . ?
C29 C25 C28 P3 -177.72(15) . . . . ?
C24 C25 C28 P3 -52.78(15) . . . . ?
C26 C25 C28 P3 53.74(15) . . . . ?
C27 P3 C28 C25 -51.30(13) . . . . ?
C23 P3 C28 C25 51.39(13) . . . . ?
S3 P3 C28 C25 178.51(9) . . . . ?
C26 O3 C31 C24 9.6(2) . . . . ?
C25 C24 C31 O3 -31.6(2) . . . . ?
C23 C24 C31 O3 85.2(2) . . . . ?
P4 O4 C32 C23 119.66(15) . . . . ?
C24 C23 C32 O4 60.9(2) . . . . ?
P3 C23 C32 O4 -178.35(12) . . . . ?
O4 P4 C33 C34 26.71(18) . . . . ?
C39 P4 C33 C34 -79.17(18) . . . . ?
S4 P4 C33 C34 153.06(15) . . . . ?
O4 P4 C33 C38 -154.15(15) . . . . ?
C39 P4 C33 C38 99.97(17) . . . . ?
S4 P4 C33 C38 -27.80(17) . . . . ?
C38 C33 C34 C35 0.5(3) . . . . ?
P4 C33 C34 C35 179.60(17) . . . . ?
C33 C34 C35 C36 -1.4(4) . . . . ?
C34 C35 C36 C37 0.6(4) . . . . ?
C35 C36 C37 C38 1.1(4) . . . . ?
C36 C37 C38 C33 -2.0(3) . . . . ?
C34 C33 C38 C37 1.2(3) . . . . ?
P4 C33 C38 C37 -177.95(17) . . . . ?
O4 P4 C39 C44 148.68(15) . . . . ?
C33 P4 C39 C44 -102.62(16) . . . . ?
S4 P4 C39 C44 24.14(17) . . . . ?
O4 P4 C39 C40 -32.84(17) . . . . ?
C33 P4 C39 C40 75.86(18) . . . . ?
S4 P4 C39 C40 -157.39(14) . . . . ?
C44 C39 C40 C41 -0.8(3) . . . . ?
P4 C39 C40 C41 -179.22(17) . . . . ?
C39 C40 C41 C42 0.5(3) . . . . ?
C40 C41 C42 C43 -0.1(3) . . . . ?
C41 C42 C43 C44 -0.1(3) . . . . ?
C42 C43 C44 C39 -0.2(3) . . . . ?
C40 C39 C44 C43 0.6(3) . . . . ?
P4 C39 C44 C43 179.11(15) . . . . ?
####################################################################### 
# 
# 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_x1775
_database_code_depnum_ccdc_archive 'CCDC 989754'
_audit_update_record             
;
2014-03-03 deposited with the CCDC.
2015-07-30 downloaded from the CCDC.
;

_audit_creation_date             2014-03-03T16:50:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C28 H38 O2 P2 S2'
_chemical_formula_weight         532.64
_chemical_absolute_configuration rmad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.4597(2)
_cell_length_b                   14.4132(2)
_cell_length_c                   23.4346(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2857.41(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    20426
_cell_measurement_theta_min      2.958
_cell_measurement_theta_max      31.789

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.95731
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.356
_diffrn_orient_matrix_ub_11      -0.0572038
_diffrn_orient_matrix_ub_12      -0.0340523
_diffrn_orient_matrix_ub_13      0.0071195
_diffrn_orient_matrix_ub_21      -0.0065197
_diffrn_orient_matrix_ub_22      -0.0124078
_diffrn_orient_matrix_ub_23      -0.0292015
_diffrn_orient_matrix_ub_31      0.0609629
_diffrn_orient_matrix_ub_32      -0.033278
_diffrn_orient_matrix_ub_33      0.003591
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_number            54563
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             7094
_reflns_number_gt                6824
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SIR92 (Giacovazzo 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 for Windows (L. J. Farrugia, 1997)'
_computing_publication_material  'WINGX  (L.J. 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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0353P)²+0.5175P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7094
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   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
S S 0.1246 0.1234 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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 0.55480(5) 0.21337(3) 0.445170(16) 0.02986(9) Uani 1 1 d . . .
S2 S 0.29519(5) 0.45271(3) 0.697775(17) 0.02889(9) Uani 1 1 d . . .
P1 P 0.57706(4) 0.17722(3) 0.524831(15) 0.02060(8) Uani 1 1 d . . .
P2 P 0.45500(4) 0.49454(2) 0.644490(14) 0.01758(7) Uani 1 1 d . . .
O1 O 0.44030(15) 0.13822(8) 0.66163(5) 0.0355(3) Uani 1 1 d . . .
O2 O 0.56170(12) 0.41128(6) 0.62072(4) 0.0201(2) Uani 1 1 d . . .
C1 C 0.62088(16) 0.26675(10) 0.57786(6) 0.0189(3) Uani 1 1 d . . .
C2 C 0.67446(18) 0.20972(10) 0.63112(6) 0.0209(3) Uani 1 1 d . . .
C3 C 0.68456(19) 0.10579(10) 0.61344(6) 0.0238(3) Uani 1 1 d . . .
C4 C 0.5050(2) 0.08064(11) 0.61751(7) 0.0296(3) Uani 1 1 d . . .
C5 C 0.4269(2) 0.10826(11) 0.55991(7) 0.0300(3) Uani 1 1 d . . .
C6 C 0.73311(19) 0.10258(10) 0.55037(6) 0.0230(3) Uani 1 1 d . . .
C7 C 0.5555(2) 0.20524(11) 0.67922(6) 0.0290(3) Uani 1 1 d . . .
C8 C 0.49197(17) 0.33798(10) 0.58642(6) 0.0208(3) Uani 1 1 d . . .
C9 C 0.7954(2) 0.05022(11) 0.65170(7) 0.0340(4) Uani 1 1 d . . .
H9A H 0.7593 0.0545 0.6914 0.051 Uiso 1 1 calc R . .
H9B H 0.9027 0.0754 0.6487 0.051 Uiso 1 1 calc R . .
H9C H 0.7954 -0.0149 0.6396 0.051 Uiso 1 1 calc R . .
C10 C 0.4675(3) -0.01973(12) 0.63294(10) 0.0468(5) Uani 1 1 d . . .
H10A H 0.5183 -0.0354 0.6693 0.07 Uiso 1 1 calc R . .
H10B H 0.5073 -0.0609 0.6029 0.07 Uiso 1 1 calc R . .
H10C H 0.3528 -0.0274 0.6365 0.07 Uiso 1 1 calc R . .
C11 C 0.39429(16) 0.55272(10) 0.57828(6) 0.0200(3) Uani 1 1 d . . .
C12 C 0.23713(18) 0.58136(10) 0.56683(7) 0.0257(3) Uani 1 1 d . . .
C13 C 0.2068(2) 0.63269(11) 0.51738(8) 0.0307(3) Uani 1 1 d . . .
C14 C 0.3234(2) 0.65548(11) 0.47873(7) 0.0325(4) Uani 1 1 d . . .
C15 C 0.4758(2) 0.62461(11) 0.48964(7) 0.0298(3) Uani 1 1 d . . .
C16 C 0.51458(18) 0.57368(10) 0.53827(6) 0.0232(3) Uani 1 1 d . . .
C17 C 0.09642(19) 0.56138(14) 0.60415(8) 0.0382(4) Uani 1 1 d . . .
H17A H 0.0022 0.5906 0.5878 0.057 Uiso 1 1 calc R . .
H17B H 0.1153 0.5863 0.6425 0.057 Uiso 1 1 calc R . .
H17C H 0.0802 0.4942 0.6065 0.057 Uiso 1 1 calc R . .
C18 C 0.2873(3) 0.71045(13) 0.42568(8) 0.0463(5) Uani 1 1 d . . .
H18A H 0.256 0.6681 0.395 0.07 Uiso 1 1 calc R . .
H18B H 0.3815 0.7452 0.414 0.07 Uiso 1 1 calc R . .
H18C H 0.2008 0.7539 0.4335 0.07 Uiso 1 1 calc R . .
C19 C 0.68524(18) 0.54455(12) 0.54370(7) 0.0292(3) Uani 1 1 d . . .
H19A H 0.6946 0.478 0.5357 0.044 Uiso 1 1 calc R . .
H19B H 0.7223 0.5571 0.5826 0.044 Uiso 1 1 calc R . .
H19C H 0.7496 0.5796 0.5164 0.044 Uiso 1 1 calc R . .
C20 C 0.60151(16) 0.56799(10) 0.67856(6) 0.0190(3) Uani 1 1 d . . .
C21 C 0.57426(17) 0.66461(9) 0.68275(5) 0.0189(3) Uani 1 1 d . . .
C22 C 0.68831(18) 0.72078(10) 0.70801(6) 0.0233(3) Uani 1 1 d . . .
C23 C 0.82760(18) 0.68526(11) 0.72971(7) 0.0278(3) Uani 1 1 d . . .
C24 C 0.8486(2) 0.58984(12) 0.72812(7) 0.0301(3) Uani 1 1 d . . .
C25 C 0.73844(19) 0.53023(10) 0.70417(7) 0.0269(3) Uani 1 1 d . . .
C26 C 0.42359(19) 0.71155(10) 0.66333(6) 0.0254(3) Uani 1 1 d . . .
H26A H 0.4126 0.7714 0.6828 0.038 Uiso 1 1 calc R . .
H26B H 0.3329 0.6721 0.6726 0.038 Uiso 1 1 calc R . .
H26C H 0.4278 0.7216 0.622 0.038 Uiso 1 1 calc R . .
C27 C 0.9496(2) 0.74811(14) 0.75645(10) 0.0479(5) Uani 1 1 d . . .
H27A H 0.954 0.8067 0.7353 0.072 Uiso 1 1 calc R . .
H27B H 1.0533 0.7179 0.7552 0.072 Uiso 1 1 calc R . .
H27C H 0.9206 0.7605 0.7962 0.072 Uiso 1 1 calc R . .
C28 C 0.7730(3) 0.42761(12) 0.70924(10) 0.0499(6) Uani 1 1 d . . .
H28A H 0.8179 0.4049 0.6733 0.075 Uiso 1 1 calc R . .
H28B H 0.6749 0.3941 0.7175 0.075 Uiso 1 1 calc R . .
H28C H 0.8488 0.4173 0.7402 0.075 Uiso 1 1 calc R . .
H1 H 0.713(2) 0.2971(13) 0.5626(8) 0.033(5) Uiso 1 1 d . . .
H2 H 0.771(2) 0.2299(12) 0.6444(7) 0.023(4) Uiso 1 1 d . . .
H5A H 0.407(2) 0.0541(14) 0.5350(8) 0.042(6) Uiso 1 1 d . . .
H5B H 0.330(2) 0.1402(13) 0.5665(8) 0.028(5) Uiso 1 1 d . . .
H6A H 0.842(2) 0.1318(11) 0.5428(7) 0.021(4) Uiso 1 1 d . . .
H6B H 0.723(2) 0.0425(14) 0.5340(8) 0.036(5) Uiso 1 1 d . . .
H7A H 0.609(2) 0.1842(13) 0.7149(8) 0.029(5) Uiso 1 1 d . . .
H7B H 0.506(2) 0.2642(13) 0.6862(8) 0.031(5) Uiso 1 1 d . . .
H8A H 0.402(2) 0.3144(12) 0.6046(7) 0.023(4) Uiso 1 1 d . . .
H8B H 0.4607(19) 0.3620(11) 0.5502(7) 0.013(4) Uiso 1 1 d . . .
H13 H 0.095(2) 0.6519(14) 0.5095(8) 0.036(5) Uiso 1 1 d . . .
H15 H 0.553(2) 0.6372(12) 0.4661(8) 0.023(4) Uiso 1 1 d . . .
H22 H 0.666(2) 0.7882(13) 0.7115(7) 0.026(4) Uiso 1 1 d . . .
H24 H 0.933(2) 0.5656(13) 0.7457(8) 0.037(5) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 P1 1.9473(5) . ?
S2 P2 1.9366(5) . ?
P1 C6 1.8052(15) . ?
P1 C5 1.8102(17) . ?
P1 C1 1.8295(14) . ?
P2 O2 1.6016(10) . ?
P2 C20 1.8150(14) . ?
P2 C11 1.8369(14) . ?
O1 C4 1.434(2) . ?
O1 C7 1.433(2) . ?
O2 C8 1.4527(16) . ?
C1 C8 1.5111(19) . ?
C1 C2 1.5618(19) . ?
C1 H1 0.97(2) . ?
C2 C7 1.512(2) . ?
C2 C3 1.556(2) . ?
C2 H2 0.919(18) . ?
C3 C9 1.525(2) . ?
C3 C6 1.535(2) . ?
C3 C4 1.564(2) . ?
C4 C10 1.525(2) . ?
C4 C5 1.555(2) . ?
C5 H5A 0.99(2) . ?
C5 H5B 0.950(19) . ?
C6 H6A 1.028(18) . ?
C6 H6B 0.95(2) . ?
C7 H7A 0.996(19) . ?
C7 H7B 0.960(19) . ?
C8 H8A 0.935(18) . ?
C8 H8B 0.955(15) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C16 1.416(2) . ?
C11 C12 1.418(2) . ?
C12 C13 1.399(2) . ?
C12 C17 1.505(2) . ?
C13 C14 1.379(3) . ?
C13 H13 1.00(2) . ?
C14 C15 1.387(3) . ?
C14 C18 1.506(2) . ?
C15 C16 1.395(2) . ?
C15 H15 0.872(19) . ?
C16 C19 1.509(2) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 C25 1.414(2) . ?
C20 C21 1.4150(19) . ?
C21 C22 1.392(2) . ?
C21 C26 1.513(2) . ?
C22 C23 1.382(2) . ?
C22 H22 0.994(18) . ?
C23 C24 1.387(2) . ?
C23 C27 1.509(2) . ?
C24 C25 1.386(2) . ?
C24 H24 0.89(2) . ?
C25 C28 1.512(2) . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 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
C6 P1 C5 92.02(8) . . ?
C6 P1 C1 92.69(7) . . ?
C5 P1 C1 102.76(7) . . ?
C6 P1 S1 123.23(5) . . ?
C5 P1 S1 120.96(6) . . ?
C1 P1 S1 118.82(5) . . ?
O2 P2 C20 101.84(6) . . ?
O2 P2 C11 101.88(6) . . ?
C20 P2 C11 107.23(6) . . ?
O2 P2 S2 112.60(4) . . ?
C20 P2 S2 112.00(5) . . ?
C11 P2 S2 119.44(5) . . ?
C4 O1 C7 109.74(12) . . ?
C8 O2 P2 120.57(9) . . ?
C8 C1 C2 117.46(12) . . ?
C8 C1 P1 115.03(10) . . ?
C2 C1 P1 103.32(9) . . ?
C8 C1 H1 109.0(11) . . ?
C2 C1 H1 107.4(11) . . ?
P1 C1 H1 103.4(11) . . ?
C7 C2 C3 101.18(12) . . ?
C7 C2 C1 115.15(13) . . ?
C3 C2 C1 108.04(11) . . ?
C7 C2 H2 110.5(11) . . ?
C3 C2 H2 110.3(11) . . ?
C1 C2 H2 111.2(11) . . ?
C9 C3 C6 112.70(13) . . ?
C9 C3 C2 112.50(13) . . ?
C6 C3 C2 107.47(12) . . ?
C9 C3 C4 116.06(13) . . ?
C6 C3 C4 108.15(13) . . ?
C2 C3 C4 98.83(12) . . ?
O1 C4 C10 107.37(14) . . ?
O1 C4 C5 108.39(13) . . ?
C10 C4 C5 111.12(15) . . ?
O1 C4 C3 106.29(13) . . ?
C10 C4 C3 115.88(15) . . ?
C5 C4 C3 107.48(13) . . ?
C4 C5 P1 103.69(11) . . ?
C4 C5 H5A 112.5(12) . . ?
P1 C5 H5A 106.5(12) . . ?
C4 C5 H5B 110.4(11) . . ?
P1 C5 H5B 114.2(11) . . ?
H5A C5 H5B 109.3(16) . . ?
C3 C6 P1 96.06(10) . . ?
C3 C6 H6A 113.1(9) . . ?
P1 C6 H6A 110.7(9) . . ?
C3 C6 H6B 113.1(12) . . ?
P1 C6 H6B 110.2(12) . . ?
H6A C6 H6B 112.5(15) . . ?
O1 C7 C2 105.48(12) . . ?
O1 C7 H7A 110.1(11) . . ?
C2 C7 H7A 109.8(10) . . ?
O1 C7 H7B 110.6(11) . . ?
C2 C7 H7B 112.1(11) . . ?
H7A C7 H7B 108.8(15) . . ?
O2 C8 C1 105.93(11) . . ?
O2 C8 H8A 110.0(11) . . ?
C1 C8 H8A 113.6(11) . . ?
O2 C8 H8B 109.9(9) . . ?
C1 C8 H8B 109.2(9) . . ?
H8A C8 H8B 108.2(14) . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 119.09(13) . . ?
C16 C11 P2 117.11(10) . . ?
C12 C11 P2 123.71(11) . . ?
C13 C12 C11 118.89(15) . . ?
C13 C12 C17 115.95(14) . . ?
C11 C12 C17 125.17(14) . . ?
C14 C13 C12 122.59(15) . . ?
C14 C13 H13 119.3(11) . . ?
C12 C13 H13 118.1(11) . . ?
C13 C14 C15 117.88(15) . . ?
C13 C14 C18 121.47(17) . . ?
C15 C14 C18 120.64(18) . . ?
C14 C15 C16 122.53(16) . . ?
C14 C15 H15 120.7(12) . . ?
C16 C15 H15 116.8(12) . . ?
C15 C16 C11 118.97(14) . . ?
C15 C16 C19 116.13(14) . . ?
C11 C16 C19 124.90(13) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.88(13) . . ?
C25 C20 P2 121.45(11) . . ?
C21 C20 P2 119.56(10) . . ?
C22 C21 C20 119.28(13) . . ?
C22 C21 C26 116.87(13) . . ?
C20 C21 C26 123.80(13) . . ?
C23 C22 C21 122.16(14) . . ?
C23 C22 H22 119.6(10) . . ?
C21 C22 H22 118.2(10) . . ?
C22 C23 C24 117.80(14) . . ?
C22 C23 C27 120.90(15) . . ?
C24 C23 C27 121.25(15) . . ?
C25 C24 C23 122.65(15) . . ?
C25 C24 H24 118.7(13) . . ?
C23 C24 H24 118.5(13) . . ?
C24 C25 C20 118.95(14) . . ?
C24 C25 C28 116.38(14) . . ?
C20 C25 C28 124.65(14) . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C20 P2 O2 C8 -175.88(10) . . . . ?
C11 P2 O2 C8 -65.18(11) . . . . ?
S2 P2 O2 C8 64.00(11) . . . . ?
C6 P1 C1 C8 -163.73(12) . . . . ?
C5 P1 C1 C8 -71.05(12) . . . . ?
S1 P1 C1 C8 65.57(12) . . . . ?
C6 P1 C1 C2 -34.42(10) . . . . ?
C5 P1 C1 C2 58.26(11) . . . . ?
S1 P1 C1 C2 -165.12(7) . . . . ?
C8 C1 C2 C7 21.77(18) . . . . ?
P1 C1 C2 C7 -106.04(12) . . . . ?
C8 C1 C2 C3 133.99(13) . . . . ?
P1 C1 C2 C3 6.18(13) . . . . ?
C7 C2 C3 C9 -82.01(16) . . . . ?
C1 C2 C3 C9 156.65(13) . . . . ?
C7 C2 C3 C6 153.35(13) . . . . ?
C1 C2 C3 C6 32.02(16) . . . . ?
C7 C2 C3 C4 41.06(14) . . . . ?
C1 C2 C3 C4 -80.28(13) . . . . ?
C7 O1 C4 C10 132.97(15) . . . . ?
C7 O1 C4 C5 -106.91(15) . . . . ?
C7 O1 C4 C3 8.36(17) . . . . ?
C9 C3 C4 O1 89.43(15) . . . . ?
C6 C3 C4 O1 -142.80(13) . . . . ?
C2 C3 C4 O1 -31.04(14) . . . . ?
C9 C3 C4 C10 -29.7(2) . . . . ?
C6 C3 C4 C10 98.03(17) . . . . ?
C2 C3 C4 C10 -150.21(15) . . . . ?
C9 C3 C4 C5 -154.68(13) . . . . ?
C6 C3 C4 C5 -26.91(16) . . . . ?
C2 C3 C4 C5 84.84(14) . . . . ?
O1 C4 C5 P1 102.72(12) . . . . ?
C10 C4 C5 P1 -139.53(13) . . . . ?
C3 C4 C5 P1 -11.78(14) . . . . ?
C6 P1 C5 C4 38.52(11) . . . . ?
C1 P1 C5 C4 -54.70(12) . . . . ?
S1 P1 C5 C4 169.87(8) . . . . ?
C9 C3 C6 P1 -178.55(11) . . . . ?
C2 C3 C6 P1 -54.03(13) . . . . ?
C4 C3 C6 P1 51.78(12) . . . . ?
C5 P1 C6 C3 -51.97(10) . . . . ?
C1 P1 C6 C3 50.92(10) . . . . ?
S1 P1 C6 C3 178.35(7) . . . . ?
C4 O1 C7 C2 19.19(17) . . . . ?
C3 C2 C7 O1 -38.51(15) . . . . ?
C1 C2 C7 O1 77.69(16) . . . . ?
P2 O2 C8 C1 -173.32(9) . . . . ?
C2 C1 C8 O2 69.14(16) . . . . ?
P1 C1 C8 O2 -168.91(9) . . . . ?
O2 P2 C11 C16 -49.21(12) . . . . ?
C20 P2 C11 C16 57.34(12) . . . . ?
S2 P2 C11 C16 -173.94(9) . . . . ?
O2 P2 C11 C12 134.11(12) . . . . ?
C20 P2 C11 C12 -119.35(12) . . . . ?
S2 P2 C11 C12 9.38(14) . . . . ?
C16 C11 C12 C13 -2.5(2) . . . . ?
P2 C11 C12 C13 174.13(11) . . . . ?
C16 C11 C12 C17 177.79(15) . . . . ?
P2 C11 C12 C17 -5.6(2) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C17 C12 C13 C14 -179.26(15) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C12 C13 C14 C18 179.70(15) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C18 C14 C15 C16 179.87(15) . . . . ?
C14 C15 C16 C11 -0.2(2) . . . . ?
C14 C15 C16 C19 179.52(14) . . . . ?
C12 C11 C16 C15 2.1(2) . . . . ?
P2 C11 C16 C15 -174.74(11) . . . . ?
C12 C11 C16 C19 -177.58(14) . . . . ?
P2 C11 C16 C19 5.6(2) . . . . ?
O2 P2 C20 C25 -31.78(13) . . . . ?
C11 P2 C20 C25 -138.36(12) . . . . ?
S2 P2 C20 C25 88.76(12) . . . . ?
O2 P2 C20 C21 152.07(11) . . . . ?
C11 P2 C20 C21 45.50(13) . . . . ?
S2 P2 C20 C21 -87.38(11) . . . . ?
C25 C20 C21 C22 4.9(2) . . . . ?
P2 C20 C21 C22 -178.86(10) . . . . ?
C25 C20 C21 C26 -172.55(14) . . . . ?
P2 C20 C21 C26 3.70(19) . . . . ?
C20 C21 C22 C23 -0.5(2) . . . . ?
C26 C21 C22 C23 177.07(14) . . . . ?
C21 C22 C23 C24 -3.0(2) . . . . ?
C21 C22 C23 C27 179.52(16) . . . . ?
C22 C23 C24 C25 2.1(3) . . . . ?
C27 C23 C24 C25 179.64(17) . . . . ?
C23 C24 C25 C20 2.2(3) . . . . ?
C23 C24 C25 C28 -176.02(18) . . . . ?
C21 C20 C25 C24 -5.7(2) . . . . ?
P2 C20 C25 C24 178.16(13) . . . . ?
C21 C20 C25 C28 172.37(18) . . . . ?
P2 C20 C25 C28 -3.8(2) . . . . ?
####################################################################### 
# 
# 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_x1930
_database_code_depnum_ccdc_archive 'CCDC 989755'
_audit_update_record             
;
2014-03-03 deposited with the CCDC.
2015-07-30 downloaded from the CCDC.
;

_audit_creation_date             2014-03-03T16:54:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C22 H29 B O P2 S'
_chemical_formula_weight         414.26
_chemical_absolute_configuration rmad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.0643(3)
_cell_length_b                   9.1050(2)
_cell_length_c                   25.6653(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2118.17(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3592
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      31.542

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

_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.95707
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.356
_diffrn_orient_matrix_ub_11      -0.0569414
_diffrn_orient_matrix_ub_12      0.0032209
_diffrn_orient_matrix_ub_13      -0.0189137
_diffrn_orient_matrix_ub_21      -0.0535709
_diffrn_orient_matrix_ub_22      0.0011795
_diffrn_orient_matrix_ub_23      0.0201426
_diffrn_orient_matrix_ub_31      0.0031692
_diffrn_orient_matrix_ub_32      0.077839
_diffrn_orient_matrix_ub_33      0.0004807
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_number            12042
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             4316
_reflns_number_gt                3478
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0545P)²+0.8961P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4316
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.044
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_restrained_S_all      0.865
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   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
S S 0.1246 0.1234 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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
P1 P 0.23999(9) 0.33192(8) 0.22021(3) 0.01387(17) Uani 1 1 d . . .
P2 P 0.32445(8) 0.52520(8) 0.37489(3) 0.01362(17) Uani 1 1 d . . .
S1 S 0.25534(10) 0.12545(7) 0.23872(3) 0.02215(19) Uani 1 1 d . . .
O1 O 0.3857(2) 0.6820(2) 0.18311(9) 0.0188(5) Uani 1 1 d . . .
C6 C 0.0861(3) 0.4158(3) 0.18676(14) 0.0165(7) Uani 1 1 d . . .
H6A H 0.072 0.3761 0.1512 0.02 Uiso 1 1 calc R . .
H6B H -0.007 0.4085 0.2067 0.02 Uiso 1 1 calc R . .
C4 C 0.3050(3) 0.5624(3) 0.16064(13) 0.0163(7) Uani 1 1 d . . .
C9 C 0.0498(3) 0.6871(4) 0.16302(14) 0.0209(7) Uani 1 1 d . . .
H9A H 0.0292 0.6621 0.1266 0.031 Uiso 1 1 calc R . .
H9B H 0.0984 0.7831 0.1646 0.031 Uiso 1 1 calc R . .
H9C H -0.043 0.6908 0.1826 0.031 Uiso 1 1 calc R . .
C2 C 0.1967(3) 0.6119(3) 0.24314(13) 0.0149(7) Uani 1 1 d . . .
H2 H 0.1147 0.6649 0.2611 0.018 Uiso 1 1 calc R . .
C18 C 0.5107(4) 0.6825(3) 0.43946(12) 0.0191(7) Uani 1 1 d . . .
H18 H 0.4235 0.7319 0.4502 0.023 Uiso 1 1 calc R . .
C17 C 0.5022(3) 0.5687(3) 0.40350(12) 0.0147(7) Uani 1 1 d . . .
C3 C 0.1496(3) 0.5719(3) 0.18656(13) 0.0145(7) Uani 1 1 d . . .
C22 C 0.6299(3) 0.4970(3) 0.38859(13) 0.0188(7) Uani 1 1 d . . .
H22 H 0.6248 0.4176 0.3647 0.023 Uiso 1 1 calc R . .
C8 C 0.3657(3) 0.4603(3) 0.30945(12) 0.0151(6) Uani 1 1 d . . .
H8A H 0.4457 0.5213 0.2946 0.018 Uiso 1 1 calc R . .
H8B H 0.4021 0.3579 0.3115 0.018 Uiso 1 1 calc R . .
C19 C 0.6459(4) 0.7241(4) 0.45952(14) 0.0227(8) Uani 1 1 d . . .
H19 H 0.6507 0.8011 0.4844 0.027 Uiso 1 1 calc R . .
C7 C 0.3247(4) 0.7168(3) 0.23331(13) 0.0189(7) Uani 1 1 d . . .
H7A H 0.2894 0.8196 0.2338 0.023 Uiso 1 1 calc R . .
H7B H 0.4007 0.705 0.2607 0.023 Uiso 1 1 calc R . .
C1 C 0.2327(3) 0.4653(3) 0.27292(11) 0.0119(6) Uani 1 1 d . . .
H1 H 0.1439 0.4408 0.2944 0.014 Uiso 1 1 calc R . .
C16 C 0.1414(4) 0.3882(4) 0.44651(13) 0.0230(8) Uani 1 1 d . . .
H16 H 0.1031 0.4841 0.452 0.028 Uiso 1 1 calc R . .
C10 C 0.3067(4) 0.5815(4) 0.10195(13) 0.0216(7) Uani 1 1 d . . .
H10A H 0.2777 0.6822 0.0931 0.032 Uiso 1 1 calc R . .
H10B H 0.2372 0.5123 0.0861 0.032 Uiso 1 1 calc R . .
H10C H 0.4063 0.5623 0.0887 0.032 Uiso 1 1 calc R . .
C12 C 0.3064(4) 0.2257(4) 0.40195(14) 0.0231(8) Uani 1 1 d . . .
H12 H 0.3822 0.2086 0.3771 0.028 Uiso 1 1 calc R . .
C11 C 0.2523(4) 0.3673(3) 0.40992(11) 0.0164(6) Uani 1 1 d . . .
C5 C 0.3744(3) 0.4133(3) 0.17689(13) 0.0168(7) Uani 1 1 d . . .
H5A H 0.4696 0.4286 0.195 0.02 Uiso 1 1 calc R . .
H5B H 0.3911 0.35 0.1461 0.02 Uiso 1 1 calc R . .
C15 C 0.0857(4) 0.2725(4) 0.47495(14) 0.0283(9) Uani 1 1 d . . .
H15 H 0.0104 0.2888 0.5 0.034 Uiso 1 1 calc R . .
C21 C 0.7654(4) 0.5405(4) 0.40839(13) 0.0249(7) Uani 1 1 d . . .
H21 H 0.8529 0.4917 0.3976 0.03 Uiso 1 1 calc R . .
C14 C 0.1401(4) 0.1328(4) 0.46677(15) 0.0285(8) Uani 1 1 d . . .
H14 H 0.1023 0.0525 0.4863 0.034 Uiso 1 1 calc R . .
C20 C 0.7734(4) 0.6553(4) 0.44389(13) 0.0247(8) Uani 1 1 d . . .
H20 H 0.8661 0.6859 0.4573 0.03 Uiso 1 1 calc R . .
C13 C 0.2483(4) 0.1102(3) 0.43060(15) 0.0312(8) Uani 1 1 d . . .
H13 H 0.2845 0.0136 0.425 0.037 Uiso 1 1 calc R . .
B1 B 0.1915(4) 0.6895(4) 0.37604(17) 0.0206(8) Uani 1 1 d . . .
H23 H 0.243(3) 0.777(3) 0.3519(11) 0.011(7) Uiso 1 1 d . . .
H24 H 0.171(3) 0.732(3) 0.4186(13) 0.021(9) Uiso 1 1 d . . .
H25 H 0.089(4) 0.646(3) 0.3601(13) 0.019(9) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C6 1.807(3) . ?
P1 C5 1.808(3) . ?
P1 C1 1.819(3) . ?
P1 S1 1.9440(10) . ?
P2 C17 1.815(3) . ?
P2 C11 1.817(3) . ?
P2 C8 1.819(3) . ?
P2 B1 1.921(3) . ?
O1 C4 1.432(3) . ?
O1 C7 1.437(4) . ?
C6 C3 1.533(4) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C4 C10 1.516(5) . ?
C4 C5 1.553(4) . ?
C4 C3 1.560(4) . ?
C9 C3 1.511(4) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C2 C7 1.524(4) . ?
C2 C3 1.557(4) . ?
C2 C1 1.572(4) . ?
C2 H2 1 . ?
C18 C19 1.382(4) . ?
C18 C17 1.390(4) . ?
C18 H18 0.95 . ?
C17 C22 1.383(4) . ?
C22 C21 1.387(4) . ?
C22 H22 0.95 . ?
C8 C1 1.528(4) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C19 C20 1.375(5) . ?
C19 H19 0.95 . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C1 H1 1 . ?
C16 C15 1.377(5) . ?
C16 C11 1.389(5) . ?
C16 H16 0.95 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C12 C13 1.387(4) . ?
C12 C11 1.394(4) . ?
C12 H12 0.95 . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C15 C14 1.380(5) . ?
C15 H15 0.95 . ?
C21 C20 1.388(4) . ?
C21 H21 0.95 . ?
C14 C13 1.366(5) . ?
C14 H14 0.95 . ?
C20 H20 0.95 . ?
C13 H13 0.95 . ?
B1 H23 1.11(3) . ?
B1 H24 1.18(3) . ?
B1 H25 1.09(3) . ?

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
C6 P1 C5 93.14(15) . . ?
C6 P1 C1 92.46(14) . . ?
C5 P1 C1 102.02(14) . . ?
C6 P1 S1 125.45(11) . . ?
C5 P1 S1 119.89(11) . . ?
C1 P1 S1 117.81(10) . . ?
C17 P2 C11 106.97(14) . . ?
C17 P2 C8 105.19(14) . . ?
C11 P2 C8 105.89(14) . . ?
C17 P2 B1 112.40(16) . . ?
C11 P2 B1 112.49(16) . . ?
C8 P2 B1 113.33(16) . . ?
C4 O1 C7 109.4(2) . . ?
C3 C6 P1 95.94(19) . . ?
C3 C6 H6A 112.6 . . ?
P1 C6 H6A 112.6 . . ?
C3 C6 H6B 112.6 . . ?
P1 C6 H6B 112.6 . . ?
H6A C6 H6B 110.1 . . ?
O1 C4 C10 107.9(3) . . ?
O1 C4 C5 110.5(2) . . ?
C10 C4 C5 111.3(3) . . ?
O1 C4 C3 104.3(2) . . ?
C10 C4 C3 115.2(3) . . ?
C5 C4 C3 107.4(2) . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C2 C3 101.6(2) . . ?
C7 C2 C1 117.0(2) . . ?
C3 C2 C1 108.2(2) . . ?
C7 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120 . . ?
C17 C18 H18 120 . . ?
C22 C17 C18 119.3(3) . . ?
C22 C17 P2 121.9(2) . . ?
C18 C17 P2 118.7(2) . . ?
C9 C3 C6 114.8(3) . . ?
C9 C3 C2 112.0(2) . . ?
C6 C3 C2 108.5(3) . . ?
C9 C3 C4 114.1(3) . . ?
C6 C3 C4 106.8(2) . . ?
C2 C3 C4 99.4(2) . . ?
C21 C22 C17 120.3(3) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
C1 C8 P2 113.2(2) . . ?
C1 C8 H8A 108.9 . . ?
P2 C8 H8A 108.9 . . ?
C1 C8 H8B 108.9 . . ?
P2 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C18 C19 C20 120.8(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
O1 C7 C2 107.6(2) . . ?
O1 C7 H7A 110.2 . . ?
C2 C7 H7A 110.2 . . ?
O1 C7 H7B 110.2 . . ?
C2 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C8 C1 C2 119.2(2) . . ?
C8 C1 P1 114.0(2) . . ?
C2 C1 P1 102.29(19) . . ?
C8 C1 H1 106.9 . . ?
C2 C1 H1 106.9 . . ?
P1 C1 H1 106.9 . . ?
C15 C16 C11 121.3(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C16 C11 C12 118.7(3) . . ?
C16 C11 P2 119.1(2) . . ?
C12 C11 P2 122.2(3) . . ?
C4 C5 P1 104.5(2) . . ?
C4 C5 H5A 110.8 . . ?
P1 C5 H5A 110.8 . . ?
C4 C5 H5B 110.8 . . ?
P1 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
P2 B1 H23 106.5(15) . . ?
P2 B1 H24 111.7(16) . . ?
H23 B1 H24 110(2) . . ?
P2 B1 H25 104.5(16) . . ?
H23 B1 H25 114(2) . . ?
H24 B1 H25 110(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 P1 C6 C3 -49.8(2) . . . . ?
C1 P1 C6 C3 52.3(2) . . . . ?
S1 P1 C6 C3 179.49(15) . . . . ?
C7 O1 C4 C10 148.7(3) . . . . ?
C7 O1 C4 C5 -89.4(3) . . . . ?
C7 O1 C4 C3 25.7(3) . . . . ?
C19 C18 C17 C22 0.6(5) . . . . ?
C19 C18 C17 P2 -176.1(2) . . . . ?
C11 P2 C17 C22 83.7(3) . . . . ?
C8 P2 C17 C22 -28.6(3) . . . . ?
B1 P2 C17 C22 -152.4(3) . . . . ?
C11 P2 C17 C18 -99.7(3) . . . . ?
C8 P2 C17 C18 148.0(2) . . . . ?
B1 P2 C17 C18 24.2(3) . . . . ?
P1 C6 C3 C9 -177.5(2) . . . . ?
P1 C6 C3 C2 -51.4(2) . . . . ?
P1 C6 C3 C4 54.9(3) . . . . ?
C7 C2 C3 C9 -82.4(3) . . . . ?
C1 C2 C3 C9 153.9(3) . . . . ?
C7 C2 C3 C6 149.9(2) . . . . ?
C1 C2 C3 C6 26.1(3) . . . . ?
C7 C2 C3 C4 38.5(3) . . . . ?
C1 C2 C3 C4 -85.3(3) . . . . ?
O1 C4 C3 C9 79.4(3) . . . . ?
C10 C4 C3 C9 -38.7(4) . . . . ?
C5 C4 C3 C9 -163.3(3) . . . . ?
O1 C4 C3 C6 -152.5(3) . . . . ?
C10 C4 C3 C6 89.3(3) . . . . ?
C5 C4 C3 C6 -35.3(3) . . . . ?
O1 C4 C3 C2 -39.9(3) . . . . ?
C10 C4 C3 C2 -158.0(2) . . . . ?
C5 C4 C3 C2 77.4(3) . . . . ?
C18 C17 C22 C21 -1.5(5) . . . . ?
P2 C17 C22 C21 175.1(3) . . . . ?
C17 P2 C8 C1 -161.1(2) . . . . ?
C11 P2 C8 C1 85.8(2) . . . . ?
B1 P2 C8 C1 -38.0(3) . . . . ?
C17 C18 C19 C20 0.8(5) . . . . ?
C4 O1 C7 C2 0.0(3) . . . . ?
C3 C2 C7 O1 -25.4(3) . . . . ?
C1 C2 C7 O1 92.1(3) . . . . ?
P2 C8 C1 C2 85.6(3) . . . . ?
P2 C8 C1 P1 -153.37(15) . . . . ?
C7 C2 C1 C8 25.5(4) . . . . ?
C3 C2 C1 C8 139.4(3) . . . . ?
C7 C2 C1 P1 -101.3(3) . . . . ?
C3 C2 C1 P1 12.6(3) . . . . ?
C6 P1 C1 C8 -169.0(2) . . . . ?
C5 P1 C1 C8 -75.3(2) . . . . ?
S1 P1 C1 C8 58.2(2) . . . . ?
C6 P1 C1 C2 -39.0(2) . . . . ?
C5 P1 C1 C2 54.8(2) . . . . ?
S1 P1 C1 C2 -171.74(14) . . . . ?
C15 C16 C11 C12 0.6(5) . . . . ?
C15 C16 C11 P2 -178.4(3) . . . . ?
C13 C12 C11 C16 0.0(5) . . . . ?
C13 C12 C11 P2 178.9(3) . . . . ?
C17 P2 C11 C16 103.7(3) . . . . ?
C8 P2 C11 C16 -144.5(3) . . . . ?
B1 P2 C11 C16 -20.2(3) . . . . ?
C17 P2 C11 C12 -75.2(3) . . . . ?
C8 P2 C11 C12 36.6(3) . . . . ?
B1 P2 C11 C12 160.9(3) . . . . ?
O1 C4 C5 P1 110.7(2) . . . . ?
C10 C4 C5 P1 -129.5(2) . . . . ?
C3 C4 C5 P1 -2.5(3) . . . . ?
C6 P1 C5 C4 31.6(2) . . . . ?
C1 P1 C5 C4 -61.6(2) . . . . ?
S1 P1 C5 C4 166.18(16) . . . . ?
C11 C16 C15 C14 -0.5(5) . . . . ?
C17 C22 C21 C20 0.8(5) . . . . ?
C16 C15 C14 C13 -0.1(5) . . . . ?
C18 C19 C20 C21 -1.4(5) . . . . ?
C22 C21 C20 C19 0.6(5) . . . . ?
C15 C14 C13 C12 0.6(6) . . . . ?
C11 C12 C13 C14 -0.6(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_x1739
_database_code_depnum_ccdc_archive 'CCDC 990595'
_audit_update_record             
;
2014-03-07 deposited with the CCDC.
2015-07-30 downloaded from the CCDC.
;

_audit_creation_date             2014-01-15T10:47:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C25 H34 N O3 P S'
_chemical_formula_weight         459.56
_chemical_absolute_configuration rmad

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   12.01550(10)
_cell_length_b                   12.26580(10)
_cell_length_c                   16.7128(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2463.13(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    33006
_cell_measurement_theta_min      2.9437
_cell_measurement_theta_max      37.3967

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.98908
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.356
_diffrn_orient_matrix_ub_11      -0.0249247
_diffrn_orient_matrix_ub_12      0.0305254
_diffrn_orient_matrix_ub_13      -0.0312732
_diffrn_orient_matrix_ub_21      -0.0122189
_diffrn_orient_matrix_ub_22      0.0425153
_diffrn_orient_matrix_ub_23      0.0273816
_diffrn_orient_matrix_ub_31      0.0521319
_diffrn_orient_matrix_ub_32      0.0245479
_diffrn_orient_matrix_ub_33      -0.0085488
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_number            55234
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             7533
_reflns_number_gt                7219
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SIR92 (Giacovazzo 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 for Windows (L. J. Farrugia, 1997)'
_computing_publication_material  'WINGX  (L.J. 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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.1921P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7533
_refine_ls_number_parameters     416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0644
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(3)
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   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
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'
O O 0.0106 0.006 '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'
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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.489835(19) 0.723153(18) 0.563558(14) 0.01575(5) Uani 1 1 d . . .
S1 S 0.51986(2) 0.74693(2) 0.675607(14) 0.02578(6) Uani 1 1 d . . .
O1 O 0.53912(8) 0.56829(8) 0.30175(5) 0.0358(2) Uani 1 1 d . . .
O2 O 0.57629(7) 0.50240(6) 0.42345(5) 0.02636(17) Uani 1 1 d . . .
O3 O 0.72446(6) 0.51617(6) 0.51157(5) 0.02128(14) Uani 1 1 d . . .
N1 N 0.20436(7) 0.54687(8) 0.56433(6) 0.02507(18) Uani 1 1 d . . .
C1 C 0.60050(8) 0.66519(7) 0.49941(6) 0.01750(16) Uani 1 1 d . . .
C2 C 0.56165(8) 0.69301(8) 0.41425(6) 0.01942(18) Uani 1 1 d . . .
C3 C 0.44278(8) 0.74801(8) 0.42046(5) 0.01844(16) Uani 1 1 d . . .
C4 C 0.36133(8) 0.66135(8) 0.45157(6) 0.01753(17) Uani 1 1 d . . .
C5 C 0.37343(8) 0.64076(7) 0.53077(6) 0.01690(16) Uani 1 1 d . . .
C6 C 0.45922(8) 0.82733(8) 0.49086(6) 0.01878(17) Uani 1 1 d . . .
C7 C 0.55830(9) 0.58508(9) 0.37114(7) 0.0244(2) Uani 1 1 d . . .
C8 C 0.61336(8) 0.54089(8) 0.50102(6) 0.02006(17) Uani 1 1 d . . .
C9 C 0.40818(11) 0.80426(10) 0.34301(7) 0.0276(2) Uani 1 1 d . . .
C10 C 0.28678(9) 0.60196(10) 0.39490(6) 0.02407(19) Uani 1 1 d . . .
C11 C 0.74941(8) 0.40039(8) 0.51748(7) 0.02111(18) Uani 1 1 d . . .
C12 C 0.86391(9) 0.38338(8) 0.48029(7) 0.02314(19) Uani 1 1 d . . .
C13 C 0.89539(11) 0.26246(10) 0.48953(9) 0.0353(3) Uani 1 1 d . . .
C14 C 0.89384(11) 0.22730(10) 0.57694(9) 0.0378(3) Uani 1 1 d . . .
C15 C 0.78081(11) 0.24601(10) 0.61578(8) 0.0319(2) Uani 1 1 d . . .
C16 C 0.74637(10) 0.36572(9) 0.60486(7) 0.0276(2) Uani 1 1 d . . .
C17 C 0.87364(10) 0.42737(9) 0.39418(7) 0.0280(2) Uani 1 1 d . . .
C18 C 0.99437(13) 0.42682(13) 0.36598(9) 0.0417(3) Uani 1 1 d . . .
C19 C 0.79923(12) 0.36925(13) 0.33371(8) 0.0375(3) Uani 1 1 d . . .
C20 C 0.78091(16) 0.21465(14) 0.70394(10) 0.0476(3) Uani 1 1 d . . .
C21 C 0.31282(8) 0.56218(8) 0.58100(6) 0.01802(17) Uani 1 1 d . . .
C22 C 0.36543(9) 0.50910(8) 0.64442(6) 0.02079(18) Uani 1 1 d . . .
C23 C 0.30512(10) 0.43640(9) 0.69087(6) 0.0243(2) Uani 1 1 d . . .
C24 C 0.19476(10) 0.41882(9) 0.67287(7) 0.0282(2) Uani 1 1 d . . .
C25 C 0.14859(10) 0.47578(10) 0.60982(8) 0.0303(2) Uani 1 1 d . . .
H1 H 0.6703(13) 0.6935(13) 0.5121(9) 0.031(4) Uiso 1 1 d . . .
H2 H 0.6104(12) 0.7456(12) 0.3870(8) 0.023(3) Uiso 1 1 d . . .
H6A H 0.5224(11) 0.8755(11) 0.4822(8) 0.020(3) Uiso 1 1 d . . .
H6B H 0.3879(13) 0.8656(12) 0.5036(9) 0.027(4) Uiso 1 1 d . . .
H8 H 0.5664(11) 0.5022(11) 0.5399(8) 0.019(3) Uiso 1 1 d . . .
H9A H 0.4079(14) 0.7560(14) 0.3009(11) 0.041(4) Uiso 1 1 d . . .
H9B H 0.3361(14) 0.8322(14) 0.3501(10) 0.038(4) Uiso 1 1 d . . .
H9C H 0.4636(13) 0.8601(14) 0.3313(10) 0.035(4) Uiso 1 1 d . . .
H10A H 0.2489(14) 0.5403(14) 0.4187(10) 0.040(4) Uiso 1 1 d . . .
H10B H 0.2305(13) 0.6494(13) 0.3758(9) 0.033(4) Uiso 1 1 d . . .
H10C H 0.3279(13) 0.5746(13) 0.3491(10) 0.030(4) Uiso 1 1 d . . .
H11 H 0.6967(11) 0.3605(11) 0.4845(8) 0.017(3) Uiso 1 1 d . . .
H12 H 0.9177(13) 0.4240(13) 0.5128(10) 0.034(4) Uiso 1 1 d . . .
H13A H 0.8399(16) 0.2187(16) 0.4581(11) 0.053(5) Uiso 1 1 d . . .
H13B H 0.9695(14) 0.2539(13) 0.4675(10) 0.040(4) Uiso 1 1 d . . .
H14A H 0.9510(16) 0.2713(15) 0.6037(11) 0.043(4) Uiso 1 1 d . . .
H14B H 0.9108(15) 0.1500(15) 0.5825(10) 0.040(4) Uiso 1 1 d . . .
H15 H 0.7283(14) 0.2019(14) 0.5856(9) 0.034(4) Uiso 1 1 d . . .
H16A H 0.7976(13) 0.4106(13) 0.6351(9) 0.028(4) Uiso 1 1 d . . .
H16B H 0.6703(13) 0.3774(13) 0.6262(9) 0.029(4) Uiso 1 1 d . . .
H17 H 0.8439(13) 0.5017(13) 0.3960(9) 0.027(4) Uiso 1 1 d . . .
H18A H 1.0459(17) 0.4618(16) 0.4069(12) 0.053(5) Uiso 1 1 d . . .
H18B H 0.9953(18) 0.4649(17) 0.3185(12) 0.057(5) Uiso 1 1 d . . .
H18C H 1.0188(17) 0.3518(17) 0.3582(12) 0.051(5) Uiso 1 1 d . . .
H19A H 0.8043(17) 0.4053(17) 0.2793(12) 0.057(6) Uiso 1 1 d . . .
H19B H 0.8192(16) 0.2911(17) 0.3294(10) 0.049(5) Uiso 1 1 d . . .
H19C H 0.7178(17) 0.3658(16) 0.3513(12) 0.052(5) Uiso 1 1 d . . .
H20A H 0.8022(18) 0.1417(18) 0.7095(12) 0.057(6) Uiso 1 1 d . . .
H20B H 0.8397(19) 0.2603(19) 0.7353(13) 0.068(6) Uiso 1 1 d . . .
H20C H 0.7052(19) 0.2285(19) 0.7326(12) 0.068(6) Uiso 1 1 d . . .
H22 H 0.4434(13) 0.5256(12) 0.6563(9) 0.028(4) Uiso 1 1 d . . .
H23 H 0.3415(13) 0.4059(14) 0.7388(10) 0.033(4) Uiso 1 1 d . . .
H24 H 0.1472(15) 0.3663(15) 0.7030(11) 0.044(5) Uiso 1 1 d . . .
H25 H 0.0705(13) 0.4655(12) 0.5961(9) 0.028(4) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C6 1.8013(10) . ?
P1 C5 1.8105(10) . ?
P1 C1 1.8502(9) . ?
P1 S1 1.9293(3) . ?
O1 C7 1.2002(14) . ?
O2 C7 1.3563(14) . ?
O2 C8 1.4499(13) . ?
O3 C8 1.3802(12) . ?
O3 C11 1.4548(11) . ?
N1 C25 1.3369(14) . ?
N1 C21 1.3459(13) . ?
C1 C8 1.5327(13) . ?
C1 C2 1.5362(14) . ?
C1 H1 0.933(16) . ?
C2 C7 1.5077(14) . ?
C2 C3 1.5830(14) . ?
C2 H2 0.983(14) . ?
C3 C9 1.5246(14) . ?
C3 C4 1.5356(13) . ?
C3 C6 1.5395(13) . ?
C4 C5 1.3554(13) . ?
C4 C10 1.4933(14) . ?
C5 C21 1.4711(13) . ?
C6 H6A 0.973(14) . ?
C6 H6B 1.000(15) . ?
C8 H8 0.983(14) . ?
C9 H9A 0.920(18) . ?
C9 H9B 0.939(17) . ?
C9 H9C 0.975(17) . ?
C10 H10A 0.968(17) . ?
C10 H10B 0.947(16) . ?
C10 H10C 0.971(16) . ?
C11 C16 1.5214(16) . ?
C11 C12 1.5241(14) . ?
C11 H11 0.972(13) . ?
C12 C13 1.5385(15) . ?
C12 C17 1.5414(16) . ?
C12 H12 0.980(16) . ?
C13 C14 1.523(2) . ?
C13 H13A 1.01(2) . ?
C13 H13B 0.969(17) . ?
C14 C15 1.5227(19) . ?
C14 H14A 0.982(19) . ?
C14 H14B 0.974(18) . ?
C15 C20 1.523(2) . ?
C15 C16 1.5365(16) . ?
C15 H15 0.972(17) . ?
C16 H16A 0.968(16) . ?
C16 H16B 0.991(15) . ?
C17 C18 1.5252(19) . ?
C17 C19 1.5260(18) . ?
C17 H17 0.979(16) . ?
C18 H18A 1.02(2) . ?
C18 H18B 0.92(2) . ?
C18 H18C 0.97(2) . ?
C19 H19A 1.01(2) . ?
C19 H19B 0.99(2) . ?
C19 H19C 1.02(2) . ?
C20 H20A 0.94(2) . ?
C20 H20B 1.04(2) . ?
C20 H20C 1.04(2) . ?
C21 C22 1.3952(13) . ?
C22 C23 1.3867(15) . ?
C22 H22 0.979(15) . ?
C23 C24 1.3768(17) . ?
C23 H23 0.986(16) . ?
C24 C25 1.3807(16) . ?
C24 H24 0.998(19) . ?
C25 H25 0.974(16) . ?

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
C6 P1 C5 91.95(4) . . ?
C6 P1 C1 91.64(5) . . ?
C5 P1 C1 99.52(4) . . ?
C6 P1 S1 125.85(3) . . ?
C5 P1 S1 121.51(3) . . ?
C1 P1 S1 119.09(3) . . ?
C7 O2 C8 112.45(8) . . ?
C8 O3 C11 114.98(7) . . ?
C25 N1 C21 117.29(9) . . ?
C8 C1 C2 105.54(8) . . ?
C8 C1 P1 116.39(7) . . ?
C2 C1 P1 103.48(6) . . ?
C8 C1 H1 106.0(10) . . ?
C2 C1 H1 113.7(9) . . ?
P1 C1 H1 111.8(10) . . ?
C7 C2 C1 104.82(8) . . ?
C7 C2 C3 112.42(8) . . ?
C1 C2 C3 107.95(7) . . ?
C7 C2 H2 111.7(8) . . ?
C1 C2 H2 113.2(8) . . ?
C3 C2 H2 106.8(8) . . ?
C9 C3 C4 115.27(9) . . ?
C9 C3 C6 113.44(8) . . ?
C4 C3 C6 105.10(7) . . ?
C9 C3 C2 112.54(8) . . ?
C4 C3 C2 107.59(8) . . ?
C6 C3 C2 101.75(7) . . ?
C5 C4 C10 126.36(9) . . ?
C5 C4 C3 113.03(8) . . ?
C10 C4 C3 120.35(8) . . ?
C4 C5 C21 128.78(9) . . ?
C4 C5 P1 105.93(7) . . ?
C21 C5 P1 125.13(7) . . ?
C3 C6 P1 95.36(6) . . ?
C3 C6 H6A 111.7(8) . . ?
P1 C6 H6A 111.8(8) . . ?
C3 C6 H6B 110.5(9) . . ?
P1 C6 H6B 111.4(9) . . ?
H6A C6 H6B 114.5(12) . . ?
O1 C7 O2 121.68(10) . . ?
O1 C7 C2 128.14(11) . . ?
O2 C7 C2 110.14(9) . . ?
O3 C8 O2 109.87(8) . . ?
O3 C8 C1 108.56(8) . . ?
O2 C8 C1 106.10(8) . . ?
O3 C8 H8 111.4(8) . . ?
O2 C8 H8 104.9(8) . . ?
C1 C8 H8 115.7(8) . . ?
C3 C9 H9A 111.1(11) . . ?
C3 C9 H9B 108.0(10) . . ?
H9A C9 H9B 109.2(15) . . ?
C3 C9 H9C 107.6(9) . . ?
H9A C9 H9C 107.5(14) . . ?
H9B C9 H9C 113.5(14) . . ?
C4 C10 H10A 113.7(10) . . ?
C4 C10 H10B 110.0(9) . . ?
H10A C10 H10B 106.5(14) . . ?
C4 C10 H10C 111.3(9) . . ?
H10A C10 H10C 107.0(14) . . ?
H10B C10 H10C 108.1(13) . . ?
O3 C11 C16 109.46(8) . . ?
O3 C11 C12 106.97(8) . . ?
C16 C11 C12 112.02(9) . . ?
O3 C11 H11 108.6(8) . . ?
C16 C11 H11 112.8(8) . . ?
C12 C11 H11 106.8(8) . . ?
C11 C12 C13 108.24(9) . . ?
C11 C12 C17 113.67(9) . . ?
C13 C12 C17 114.36(10) . . ?
C11 C12 H12 107.4(9) . . ?
C13 C12 H12 105.8(9) . . ?
C17 C12 H12 106.9(10) . . ?
C14 C13 C12 111.48(10) . . ?
C14 C13 H13A 110.0(11) . . ?
C12 C13 H13A 107.4(11) . . ?
C14 C13 H13B 110.2(10) . . ?
C12 C13 H13B 107.0(10) . . ?
H13A C13 H13B 110.7(15) . . ?
C15 C14 C13 112.15(10) . . ?
C15 C14 H14A 110.3(11) . . ?
C13 C14 H14A 105.9(11) . . ?
C15 C14 H14B 107.0(10) . . ?
C13 C14 H14B 111.4(10) . . ?
H14A C14 H14B 110.2(15) . . ?
C20 C15 C14 111.95(12) . . ?
C20 C15 C16 110.89(12) . . ?
C14 C15 C16 109.49(10) . . ?
C20 C15 H15 111.2(9) . . ?
C14 C15 H15 105.9(10) . . ?
C16 C15 H15 107.2(10) . . ?
C11 C16 C15 112.01(10) . . ?
C11 C16 H16A 109.1(9) . . ?
C15 C16 H16A 108.1(9) . . ?
C11 C16 H16B 109.1(9) . . ?
C15 C16 H16B 110.1(9) . . ?
H16A C16 H16B 108.4(13) . . ?
C18 C17 C19 110.52(10) . . ?
C18 C17 C12 111.04(11) . . ?
C19 C17 C12 114.23(10) . . ?
C18 C17 H17 111.2(9) . . ?
C19 C17 H17 104.0(9) . . ?
C12 C17 H17 105.6(9) . . ?
C17 C18 H18A 111.7(11) . . ?
C17 C18 H18B 106.0(14) . . ?
H18A C18 H18B 111.0(17) . . ?
C17 C18 H18C 109.4(12) . . ?
H18A C18 H18C 107.7(16) . . ?
H18B C18 H18C 111.1(17) . . ?
C17 C19 H19A 110.8(12) . . ?
C17 C19 H19B 111.0(11) . . ?
H19A C19 H19B 110.0(15) . . ?
C17 C19 H19C 112.9(11) . . ?
H19A C19 H19C 109.5(16) . . ?
H19B C19 H19C 102.3(15) . . ?
C15 C20 H20A 109.8(13) . . ?
C15 C20 H20B 110.6(12) . . ?
H20A C20 H20B 106.2(18) . . ?
C15 C20 H20C 113.8(12) . . ?
H20A C20 H20C 110.4(18) . . ?
H20B C20 H20C 105.8(17) . . ?
N1 C21 C22 122.06(9) . . ?
N1 C21 C5 116.91(8) . . ?
C22 C21 C5 120.99(9) . . ?
C23 C22 C21 119.25(10) . . ?
C23 C22 H22 121.3(9) . . ?
C21 C22 H22 119.4(9) . . ?
C24 C23 C22 118.80(10) . . ?
C24 C23 H23 123.0(10) . . ?
C22 C23 H23 117.9(10) . . ?
C23 C24 C25 118.33(10) . . ?
C23 C24 H24 122.9(10) . . ?
C25 C24 H24 118.8(11) . . ?
N1 C25 C24 124.25(11) . . ?
N1 C25 H25 115.7(9) . . ?
C24 C25 H25 120.1(9) . . ?

# END of CIF


