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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_x1773

_audit_creation_date             2013-11-07T15:30:05-00:00
_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            'C19 H23 N P2 S2'
_chemical_formula_weight         391.44

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6302(2)
_cell_length_b                   8.7719(3)
_cell_length_c                   15.6426(6)
_cell_angle_alpha                102.400(3)
_cell_angle_beta                 94.431(3)
_cell_angle_gamma                104.341(3)
_cell_volume                     981.23(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.03
_diffrn_reflns_number            14414
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4010
_reflns_number_gt                3438
_reflns_threshold_expression     >2σ(I)

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

_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)+(0.0395P)²+0.4810P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4010
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.051

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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
S1 S 0.91434(7) 0.24778(6) 0.11104(3) 0.03025(13) Uani 1 1 d . . .
S2 S 0.66164(7) -0.14985(6) 0.39085(3) 0.02976(13) Uani 1 1 d . . .
P1 P 0.86883(6) 0.45369(6) 0.16598(3) 0.02341(12) Uani 1 1 d . . .
P2 P 0.56255(6) 0.02233(5) 0.36365(3) 0.02161(12) Uani 1 1 d . . .
N1 N 0.8575(2) 0.38784(17) 0.35600(10) 0.0223(3) Uani 1 1 d . . .
C1 C 0.6400(3) 0.4529(2) 0.18226(13) 0.0267(4) Uani 1 1 d . . .
C2 C 0.5865(3) 0.5568(2) 0.14224(13) 0.0270(4) Uani 1 1 d . . .
C3 C 0.7292(3) 0.6424(2) 0.09510(12) 0.0265(4) Uani 1 1 d . . .
C4 C 0.8848(3) 0.5993(2) 0.10067(12) 0.0262(4) Uani 1 1 d . . .
C5 C 0.4032(3) 0.5891(3) 0.14193(18) 0.0375(5) Uani 1 1 d . . .
C6 C 0.6942(4) 0.7647(3) 0.04747(16) 0.0353(5) Uani 1 1 d . . .
C7 C 1.0123(3) 0.5644(2) 0.27114(13) 0.0268(4) Uani 1 1 d . . .
C8 C 1.0197(2) 0.4613(2) 0.33624(12) 0.0235(4) Uani 1 1 d . . .
C9 C 1.1838(3) 0.4480(2) 0.37436(13) 0.0274(4) Uani 1 1 d . . .
C10 C 1.1793(3) 0.3559(2) 0.43617(13) 0.0286(4) Uani 1 1 d . . .
C11 C 1.0129(3) 0.2799(2) 0.45767(13) 0.0263(4) Uani 1 1 d . . .
C12 C 0.8551(2) 0.2997(2) 0.41650(12) 0.0222(4) Uani 1 1 d . . .
C13 C 0.6683(3) 0.2238(2) 0.43595(13) 0.0241(4) Uani 1 1 d . . .
C14 C 0.3220(2) -0.0061(2) 0.35956(13) 0.0237(4) Uani 1 1 d . . .
C15 C 0.2515(2) 0.0056(2) 0.28084(12) 0.0241(4) Uani 1 1 d . . .
C16 C 0.3893(3) 0.0340(2) 0.21884(12) 0.0244(4) Uani 1 1 d . . .
C17 C 0.5601(3) 0.0479(2) 0.25336(12) 0.0233(4) Uani 1 1 d . . .
C18 C 0.0565(3) -0.0025(3) 0.25501(15) 0.0303(4) Uani 1 1 d . . .
C19 C 0.3329(3) 0.0437(3) 0.12701(14) 0.0340(5) Uani 1 1 d . . .
H1 H 0.570(3) 0.389(3) 0.2151(14) 0.031(5) Uiso 1 1 d . . .
H4 H 0.987(3) 0.640(3) 0.0738(14) 0.032(6) Uiso 1 1 d . . .
H5A H 0.322(4) 0.508(3) 0.1630(18) 0.059(8) Uiso 1 1 d . . .
H5B H 0.412(3) 0.691(3) 0.1811(17) 0.044(7) Uiso 1 1 d . . .
H5C H 0.352(3) 0.589(3) 0.0848(18) 0.051(7) Uiso 1 1 d . . .
H6A H 0.795(4) 0.802(3) 0.0171(18) 0.060(8) Uiso 1 1 d . . .
H6B H 0.588(4) 0.721(3) 0.0071(18) 0.055(8) Uiso 1 1 d . . .
H6C H 0.675(3) 0.854(3) 0.0900(18) 0.052(7) Uiso 1 1 d . . .
H7A H 1.128(3) 0.607(2) 0.2589(13) 0.026(5) Uiso 1 1 d . . .
H7B H 0.958(3) 0.651(2) 0.2938(14) 0.027(5) Uiso 1 1 d . . .
H9 H 1.294(3) 0.501(3) 0.3590(14) 0.032(6) Uiso 1 1 d . . .
H10 H 1.287(3) 0.346(2) 0.4637(14) 0.026(5) Uiso 1 1 d . . .
H11 H 1.006(3) 0.221(2) 0.5008(14) 0.026(5) Uiso 1 1 d . . .
H13A H 0.668(3) 0.214(2) 0.4947(15) 0.028(5) Uiso 1 1 d . . .
H13B H 0.583(3) 0.282(2) 0.4252(14) 0.027(5) Uiso 1 1 d . . .
H14 H 0.258(3) -0.021(2) 0.4036(14) 0.029(5) Uiso 1 1 d . . .
H17 H 0.658(3) 0.071(2) 0.2270(14) 0.027(5) Uiso 1 1 d . . .
H18A H 0.048(3) 0.100(3) 0.2474(15) 0.039(6) Uiso 1 1 d . . .
H18B H 0.010(3) -0.080(3) 0.2020(17) 0.045(7) Uiso 1 1 d . . .
H18C H -0.015(3) -0.027(3) 0.2982(16) 0.039(6) Uiso 1 1 d . . .
H19A H 0.438(3) 0.071(3) 0.1002(16) 0.044(7) Uiso 1 1 d . . .
H19B H 0.265(3) 0.123(3) 0.1277(16) 0.043(7) Uiso 1 1 d . . .
H19C H 0.253(3) -0.055(3) 0.0960(15) 0.032(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 1.9523(7) . ?
S2 P2 1.9560(7) . ?
P1 C1 1.7823(19) . ?
P1 C4 1.7870(19) . ?
P1 C7 1.832(2) . ?
P2 C14 1.7839(19) . ?
P2 C17 1.7862(19) . ?
P2 C13 1.8296(19) . ?
N1 C8 1.339(2) . ?
N1 C12 1.343(2) . ?
C1 C2 1.334(3) . ?
C1 H1 0.94(2) . ?
C2 C5 1.494(3) . ?
C2 C3 1.500(3) . ?
C3 C4 1.334(3) . ?
C3 C6 1.494(3) . ?
C4 H4 0.94(2) . ?
C5 H5A 0.96(3) . ?
C5 H5B 0.95(3) . ?
C5 H5C 0.95(3) . ?
C6 H6A 0.96(3) . ?
C6 H6B 0.93(3) . ?
C6 H6C 0.96(3) . ?
C7 C8 1.507(3) . ?
C7 H7A 0.92(2) . ?
C7 H7B 0.97(2) . ?
C8 C9 1.387(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.93(2) . ?
C10 C11 1.383(3) . ?
C10 H10 0.93(2) . ?
C11 C12 1.388(3) . ?
C11 H11 0.93(2) . ?
C12 C13 1.501(2) . ?
C13 H13A 0.94(2) . ?
C13 H13B 0.95(2) . ?
C14 C15 1.340(3) . ?
C14 H14 0.89(2) . ?
C15 C18 1.491(3) . ?
C15 C16 1.497(3) . ?
C16 C17 1.337(3) . ?
C16 C19 1.494(3) . ?
C17 H17 0.88(2) . ?
C18 H18A 0.95(2) . ?
C18 H18B 0.93(3) . ?
C18 H18C 0.93(2) . ?
C19 H19A 0.94(2) . ?
C19 H19B 0.96(2) . ?
C19 H19C 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
C1 P1 C4 92.53(9) . . ?
C1 P1 C7 106.50(9) . . ?
C4 P1 C7 105.04(9) . . ?
C1 P1 S1 117.72(7) . . ?
C4 P1 S1 116.70(7) . . ?
C7 P1 S1 115.43(7) . . ?
C14 P2 C17 92.59(9) . . ?
C14 P2 C13 105.86(9) . . ?
C17 P2 C13 105.93(9) . . ?
C14 P2 S2 117.50(6) . . ?
C17 P2 S2 117.54(6) . . ?
C13 P2 S2 114.68(7) . . ?
C8 N1 C12 118.06(16) . . ?
C2 C1 P1 110.02(14) . . ?
C2 C1 H1 126.0(13) . . ?
P1 C1 H1 124.0(13) . . ?
C1 C2 C5 125.20(19) . . ?
C1 C2 C3 113.77(17) . . ?
C5 C2 C3 121.04(18) . . ?
C4 C3 C6 124.82(19) . . ?
C4 C3 C2 113.93(17) . . ?
C6 C3 C2 121.25(18) . . ?
C3 C4 P1 109.75(14) . . ?
C3 C4 H4 124.7(13) . . ?
P1 C4 H4 125.6(13) . . ?
C2 C5 H5A 109.2(16) . . ?
C2 C5 H5B 110.3(14) . . ?
H5A C5 H5B 107(2) . . ?
C2 C5 H5C 112.2(15) . . ?
H5A C5 H5C 109(2) . . ?
H5B C5 H5C 109(2) . . ?
C3 C6 H6A 110.8(16) . . ?
C3 C6 H6B 110.8(16) . . ?
H6A C6 H6B 109(2) . . ?
C3 C6 H6C 108.3(15) . . ?
H6A C6 H6C 111(2) . . ?
H6B C6 H6C 107(2) . . ?
C8 C7 P1 113.57(13) . . ?
C8 C7 H7A 110.1(13) . . ?
P1 C7 H7A 107.7(13) . . ?
C8 C7 H7B 110.8(12) . . ?
P1 C7 H7B 104.3(12) . . ?
H7A C7 H7B 110.2(17) . . ?
N1 C8 C9 122.92(17) . . ?
N1 C8 C7 115.10(16) . . ?
C9 C8 C7 121.96(17) . . ?
C10 C9 C8 118.41(18) . . ?
C10 C9 H9 121.2(13) . . ?
C8 C9 H9 120.4(13) . . ?
C11 C10 C9 119.40(19) . . ?
C11 C10 H10 120.1(13) . . ?
C9 C10 H10 120.5(13) . . ?
C10 C11 C12 118.49(18) . . ?
C10 C11 H11 121.3(12) . . ?
C12 C11 H11 120.1(12) . . ?
N1 C12 C11 122.71(17) . . ?
N1 C12 C13 114.73(16) . . ?
C11 C12 C13 122.56(17) . . ?
C12 C13 P2 113.03(13) . . ?
C12 C13 H13A 112.7(12) . . ?
P2 C13 H13A 107.3(12) . . ?
C12 C13 H13B 112.5(12) . . ?
P2 C13 H13B 102.8(12) . . ?
H13A C13 H13B 107.9(17) . . ?
C15 C14 P2 109.87(14) . . ?
C15 C14 H14 124.3(13) . . ?
P2 C14 H14 125.8(13) . . ?
C14 C15 C18 125.17(18) . . ?
C14 C15 C16 113.72(17) . . ?
C18 C15 C16 121.08(17) . . ?
C17 C16 C19 125.17(18) . . ?
C17 C16 C15 114.03(16) . . ?
C19 C16 C15 120.79(17) . . ?
C16 C17 P2 109.75(14) . . ?
C16 C17 H17 125.5(13) . . ?
P2 C17 H17 124.7(13) . . ?
C15 C18 H18A 109.2(14) . . ?
C15 C18 H18B 109.9(15) . . ?
H18A C18 H18B 109(2) . . ?
C15 C18 H18C 111.8(14) . . ?
H18A C18 H18C 107.2(19) . . ?
H18B C18 H18C 110(2) . . ?
C16 C19 H19A 108.5(15) . . ?
C16 C19 H19B 110.7(15) . . ?
H19A C19 H19B 110(2) . . ?
C16 C19 H19C 109.3(13) . . ?
H19A C19 H19C 112.1(19) . . ?
H19B C19 H19C 106.0(19) . . ?
_database_code_depnum_ccdc_archive 'CCDC 981040'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_x1458fin

_audit_creation_date             2013-06-09T14:48:25-00:00
_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            'C26 H35 O3 P S'
_chemical_formula_weight         458.57
_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                   7.5433(2)
_cell_length_b                   14.0457(3)
_cell_length_c                   24.3817(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2583.26(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    6453
_cell_measurement_theta_min      2.8209
_cell_measurement_theta_max      30.4507

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

_exptl_crystal_description       'thin needles'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.96262
_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      0.0283761
_diffrn_orient_matrix_ub_12      0.0475477
_diffrn_orient_matrix_ub_13      -0.0043518
_diffrn_orient_matrix_ub_21      -0.0010391
_diffrn_orient_matrix_ub_22      -0.007769
_diffrn_orient_matrix_ub_23      -0.0287553
_diffrn_orient_matrix_ub_31      -0.0896056
_diffrn_orient_matrix_ub_32      0.0151337
_diffrn_orient_matrix_ub_33      -0.0010543
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_number            23054
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             5288
_reflns_number_gt                4767
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_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)+(0.0454P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5288
_refine_ls_number_parameters     420
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0823
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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(6)
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   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 -0.04866(7) 0.53904(4) 0.38873(2) 0.02511(13) Uani 1 1 d . . .
P1 P 0.12690(7) 0.51311(3) 0.44535(2) 0.01942(12) Uani 1 1 d . . .
O1 O 0.3139(2) 0.18808(11) 0.44488(7) 0.0373(4) Uani 1 1 d . . .
O2 O 0.5111(2) 0.27941(10) 0.40222(6) 0.0283(4) Uani 1 1 d . . .
O3 O 0.50695(19) 0.34347(10) 0.31445(5) 0.0244(3) Uani 1 1 d . . .
C1 C 0.3449(3) 0.42047(14) 0.38373(8) 0.0207(4) Uani 1 1 d . . .
C2 C 0.2251(3) 0.34540(14) 0.41152(9) 0.0235(4) Uani 1 1 d . . .
C3 C 0.1631(3) 0.38857(14) 0.46764(8) 0.0222(4) Uani 1 1 d . . .
C4 C 0.3257(3) 0.40331(14) 0.50305(8) 0.0221(4) Uani 1 1 d . . .
C5 C 0.4363(3) 0.46641(14) 0.48009(7) 0.0212(4) Uani 1 1 d . . .
C6 C 0.3645(3) 0.50248(13) 0.42583(8) 0.0201(4) Uani 1 1 d . . .
C7 C 0.3471(3) 0.26136(15) 0.42174(8) 0.0277(5) Uani 1 1 d . . .
C8 C 0.5147(3) 0.36639(15) 0.36973(8) 0.0234(4) Uani 1 1 d . . .
C9 C 0.3445(3) 0.35304(18) 0.55691(10) 0.0313(5) Uani 1 1 d . . .
C10 C 0.6034(3) 0.50577(18) 0.50355(9) 0.0295(5) Uani 1 1 d . . .
C11 C 0.6565(3) 0.29007(14) 0.29272(8) 0.0241(5) Uani 1 1 d . . .
C12 C 0.5828(3) 0.22600(15) 0.24750(8) 0.0248(5) Uani 1 1 d . . .
C13 C 0.7367(3) 0.17634(17) 0.21829(11) 0.0351(6) Uani 1 1 d . . .
C14 C 0.8734(4) 0.24684(19) 0.19661(10) 0.0402(6) Uani 1 1 d . . .
C15 C 0.9487(3) 0.30923(17) 0.24241(10) 0.0348(5) Uani 1 1 d . . .
C16 C 0.7951(3) 0.35918(16) 0.27174(10) 0.0285(5) Uani 1 1 d . . .
C17 C 0.4354(3) 0.15871(15) 0.26816(9) 0.0300(5) Uani 1 1 d . . .
C18 C 0.3307(4) 0.11528(19) 0.22094(11) 0.0390(6) Uani 1 1 d . . .
C19 C 0.5004(5) 0.0804(2) 0.30659(12) 0.0479(7) Uani 1 1 d . . .
C20 C 1.0828(4) 0.3815(2) 0.22122(15) 0.0522(8) Uani 1 1 d . . .
C21 C 0.1158(3) 0.58994(14) 0.50452(8) 0.0219(4) Uani 1 1 d . . .
C22 C 0.0240(3) 0.56415(15) 0.55138(9) 0.0272(5) Uani 1 1 d . . .
C23 C 0.0132(4) 0.62653(17) 0.59531(9) 0.0378(6) Uani 1 1 d . . .
C24 C 0.0960(4) 0.71455(18) 0.59232(10) 0.0411(7) Uani 1 1 d . . .
C25 C 0.1905(4) 0.74050(17) 0.54651(11) 0.0392(6) Uani 1 1 d . . .
C26 C 0.1984(3) 0.67897(16) 0.50182(10) 0.0307(5) Uani 1 1 d . . .
H22 H -0.032(3) 0.5073(17) 0.5535(9) 0.030(6) Uiso 1 1 d . . .
H8 H 0.625(3) 0.3980(14) 0.3798(8) 0.019(5) Uiso 1 1 d . . .
H2 H 0.123(3) 0.3261(16) 0.3871(9) 0.032(6) Uiso 1 1 d . . .
H12 H 0.531(3) 0.2694(14) 0.2219(7) 0.015(5) Uiso 1 1 d . . .
H26 H 0.258(3) 0.6937(15) 0.4711(9) 0.020(6) Uiso 1 1 d . . .
H1 H 0.296(3) 0.4442(15) 0.3506(9) 0.026(6) Uiso 1 1 d . . .
H3 H 0.069(3) 0.3570(16) 0.4846(8) 0.027(6) Uiso 1 1 d . . .
H6 H 0.409(3) 0.5564(16) 0.4110(8) 0.027(6) Uiso 1 1 d . . .
H18C H 0.281(3) 0.1651(19) 0.1981(10) 0.040(7) Uiso 1 1 d . . .
H11 H 0.705(3) 0.2511(13) 0.3242(8) 0.011(5) Uiso 1 1 d . . .
H13A H 0.797(3) 0.1353(18) 0.2414(10) 0.036(7) Uiso 1 1 d . . .
H14A H 0.973(4) 0.2188(18) 0.1783(9) 0.039(7) Uiso 1 1 d . . .
H18A H 0.407(4) 0.0682(19) 0.2002(10) 0.052(8) Uiso 1 1 d . . .
H18B H 0.233(4) 0.078(2) 0.2383(11) 0.053(8) Uiso 1 1 d . . .
H20B H 1.127(4) 0.418(2) 0.2487(12) 0.063(10) Uiso 1 1 d . . .
H16A H 0.841(3) 0.3972(17) 0.3035(10) 0.038(7) Uiso 1 1 d . . .
H20A H 1.026(4) 0.426(2) 0.1924(11) 0.060(9) Uiso 1 1 d . . .
H13B H 0.689(3) 0.1336(17) 0.1880(10) 0.038(7) Uiso 1 1 d . . .
H20C H 1.180(4) 0.3511(18) 0.2024(10) 0.039(7) Uiso 1 1 d . . .
H14B H 0.811(3) 0.2910(17) 0.1653(10) 0.042(7) Uiso 1 1 d . . .
H16B H 0.733(3) 0.4010(15) 0.2470(9) 0.025(6) Uiso 1 1 d . . .
H17 H 0.353(3) 0.1953(18) 0.2892(9) 0.038(7) Uiso 1 1 d . . .
H9B H 0.458(4) 0.3611(17) 0.5713(10) 0.040(7) Uiso 1 1 d . . .
H9C H 0.258(4) 0.374(2) 0.5818(11) 0.049(8) Uiso 1 1 d . . .
H15 H 1.009(3) 0.2647(17) 0.2711(9) 0.036(7) Uiso 1 1 d . . .
H24 H 0.094(4) 0.7558(19) 0.6225(11) 0.046(8) Uiso 1 1 d . . .
H23 H -0.058(4) 0.612(2) 0.6284(11) 0.058(8) Uiso 1 1 d . . .
H9A H 0.327(4) 0.286(2) 0.5507(11) 0.051(8) Uiso 1 1 d . . .
H25 H 0.246(4) 0.801(2) 0.5444(11) 0.048(8) Uiso 1 1 d . . .
H10A H 0.696(3) 0.5056(17) 0.4785(9) 0.034(6) Uiso 1 1 d . . .
H10C H 0.589(3) 0.5714(19) 0.5125(9) 0.036(7) Uiso 1 1 d . . .
H10B H 0.640(3) 0.4717(18) 0.5357(10) 0.042(7) Uiso 1 1 d . . .
H19B H 0.387(4) 0.048(2) 0.3217(11) 0.060(9) Uiso 1 1 d . . .
H19A H 0.570(4) 0.036(2) 0.2887(11) 0.061(10) Uiso 1 1 d . . .
H19C H 0.559(4) 0.102(2) 0.3383(12) 0.062(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
S1 P1 1.9474(7) . ?
P1 C21 1.804(2) . ?
P1 C3 1.852(2) . ?
P1 C6 1.860(2) . ?
O1 C7 1.200(3) . ?
O2 C7 1.349(3) . ?
O2 C8 1.456(2) . ?
O3 C8 1.387(2) . ?
O3 C11 1.455(2) . ?
C1 C8 1.528(3) . ?
C1 C2 1.545(3) . ?
C1 C6 1.550(3) . ?
C1 H1 0.95(2) . ?
C2 C7 1.517(3) . ?
C2 C3 1.568(3) . ?
C2 H2 1.01(2) . ?
C3 C4 1.514(3) . ?
C3 H3 0.93(2) . ?
C4 C5 1.340(3) . ?
C4 C9 1.498(3) . ?
C5 C10 1.490(3) . ?
C5 C6 1.517(3) . ?
C6 H6 0.90(2) . ?
C8 H8 0.97(2) . ?
C9 H9B 0.93(3) . ?
C9 H9C 0.94(3) . ?
C9 H9A 0.96(3) . ?
C10 H10A 0.93(3) . ?
C10 H10C 0.95(3) . ?
C10 H10B 0.96(2) . ?
C11 C16 1.516(3) . ?
C11 C12 1.528(3) . ?
C11 H11 1.013(19) . ?
C12 C13 1.530(3) . ?
C12 C17 1.544(3) . ?
C12 H12 0.96(2) . ?
C13 C14 1.524(4) . ?
C13 H13A 0.93(3) . ?
C13 H13B 1.02(3) . ?
C14 C15 1.529(3) . ?
C14 H14A 0.96(3) . ?
C14 H14B 1.09(3) . ?
C15 C20 1.523(4) . ?
C15 C16 1.532(3) . ?
C15 H15 1.04(2) . ?
C16 H16A 1.00(2) . ?
C16 H16B 0.96(2) . ?
C17 C18 1.524(3) . ?
C17 C19 1.526(3) . ?
C17 H17 0.96(3) . ?
C18 H18C 0.97(3) . ?
C18 H18A 1.01(3) . ?
C18 H18B 1.00(3) . ?
C19 H19B 1.03(3) . ?
C19 H19A 0.92(3) . ?
C19 H19C 0.94(3) . ?
C20 H20B 0.91(3) . ?
C20 H20A 1.03(3) . ?
C20 H20C 0.97(3) . ?
C21 C22 1.385(3) . ?
C21 C26 1.398(3) . ?
C22 C23 1.386(3) . ?
C22 H22 0.91(2) . ?
C23 C24 1.387(4) . ?
C23 H23 0.99(3) . ?
C24 C25 1.374(4) . ?
C24 H24 0.94(3) . ?
C25 C26 1.392(3) . ?
C25 H25 0.94(3) . ?
C26 H26 0.90(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
C21 P1 C3 109.71(9) . . ?
C21 P1 C6 107.29(9) . . ?
C3 P1 C6 81.80(9) . . ?
C21 P1 S1 115.07(7) . . ?
C3 P1 S1 119.01(7) . . ?
C6 P1 S1 119.26(7) . . ?
C7 O2 C8 111.52(15) . . ?
C8 O3 C11 116.16(15) . . ?
C8 C1 C2 104.42(16) . . ?
C8 C1 C6 115.95(17) . . ?
C2 C1 C6 105.82(15) . . ?
C8 C1 H1 108.0(13) . . ?
C2 C1 H1 112.8(14) . . ?
C6 C1 H1 109.8(13) . . ?
C7 C2 C1 104.37(17) . . ?
C7 C2 C3 109.77(17) . . ?
C1 C2 C3 107.05(16) . . ?
C7 C2 H2 110.5(13) . . ?
C1 C2 H2 111.7(13) . . ?
C3 C2 H2 113.1(13) . . ?
C4 C3 C2 107.99(17) . . ?
C4 C3 P1 99.07(13) . . ?
C2 C3 P1 98.80(13) . . ?
C4 C3 H3 115.3(13) . . ?
C2 C3 H3 115.5(13) . . ?
P1 C3 H3 117.9(14) . . ?
C5 C4 C9 128.3(2) . . ?
C5 C4 C3 110.90(17) . . ?
C9 C4 C3 120.81(18) . . ?
C4 C5 C10 127.72(19) . . ?
C4 C5 C6 111.27(18) . . ?
C10 C5 C6 120.86(18) . . ?
C5 C6 C1 111.31(15) . . ?
C5 C6 P1 98.50(12) . . ?
C1 C6 P1 97.89(13) . . ?
C5 C6 H6 119.7(14) . . ?
C1 C6 H6 113.2(13) . . ?
P1 C6 H6 113.1(14) . . ?
O1 C7 O2 121.2(2) . . ?
O1 C7 C2 128.1(2) . . ?
O2 C7 C2 110.60(17) . . ?
O3 C8 O2 109.45(16) . . ?
O3 C8 C1 107.28(16) . . ?
O2 C8 C1 106.24(16) . . ?
O3 C8 H8 112.8(12) . . ?
O2 C8 H8 105.2(12) . . ?
C1 C8 H8 115.6(12) . . ?
C4 C9 H9B 111.1(15) . . ?
C4 C9 H9C 110.8(16) . . ?
H9B C9 H9C 111(2) . . ?
C4 C9 H9A 108.0(17) . . ?
H9B C9 H9A 108(2) . . ?
H9C C9 H9A 108(2) . . ?
C5 C10 H10A 112.5(15) . . ?
C5 C10 H10C 110.4(15) . . ?
H10A C10 H10C 104(2) . . ?
C5 C10 H10B 111.7(16) . . ?
H10A C10 H10B 109(2) . . ?
H10C C10 H10B 109(2) . . ?
O3 C11 C16 109.14(16) . . ?
O3 C11 C12 106.52(17) . . ?
C16 C11 C12 112.64(18) . . ?
O3 C11 H11 106.5(11) . . ?
C16 C11 H11 110.6(11) . . ?
C12 C11 H11 111.2(10) . . ?
C11 C12 C13 109.17(19) . . ?
C11 C12 C17 112.78(17) . . ?
C13 C12 C17 114.79(18) . . ?
C11 C12 H12 104.1(12) . . ?
C13 C12 H12 107.3(12) . . ?
C17 C12 H12 107.9(13) . . ?
C14 C13 C12 112.24(19) . . ?
C14 C13 H13A 106.6(16) . . ?
C12 C13 H13A 111.9(15) . . ?
C14 C13 H13B 111.8(14) . . ?
C12 C13 H13B 109.7(14) . . ?
H13A C13 H13B 104(2) . . ?
C13 C14 C15 111.7(2) . . ?
C13 C14 H14A 115.2(15) . . ?
C15 C14 H14A 106.5(15) . . ?
C13 C14 H14B 108.6(14) . . ?
C15 C14 H14B 110.2(12) . . ?
H14A C14 H14B 104.3(18) . . ?
C20 C15 C14 112.4(2) . . ?
C20 C15 C16 110.8(2) . . ?
C14 C15 C16 108.8(2) . . ?
C20 C15 H15 109.8(14) . . ?
C14 C15 H15 107.9(13) . . ?
C16 C15 H15 106.9(13) . . ?
C11 C16 C15 112.71(19) . . ?
C11 C16 H16A 108.4(14) . . ?
C15 C16 H16A 110.3(14) . . ?
C11 C16 H16B 105.5(13) . . ?
C15 C16 H16B 110.7(13) . . ?
H16A C16 H16B 109.0(18) . . ?
C18 C17 C19 110.0(2) . . ?
C18 C17 C12 111.83(19) . . ?
C19 C17 C12 114.2(2) . . ?
C18 C17 H17 106.3(15) . . ?
C19 C17 H17 105.5(14) . . ?
C12 C17 H17 108.4(15) . . ?
C17 C18 H18C 110.2(15) . . ?
C17 C18 H18A 110.3(15) . . ?
H18C C18 H18A 114(2) . . ?
C17 C18 H18B 105.9(16) . . ?
H18C C18 H18B 110(2) . . ?
H18A C18 H18B 107(2) . . ?
C17 C19 H19B 105.4(16) . . ?
C17 C19 H19A 112.2(18) . . ?
H19B C19 H19A 111(2) . . ?
C17 C19 H19C 114.8(18) . . ?
H19B C19 H19C 104(2) . . ?
H19A C19 H19C 110(3) . . ?
C15 C20 H20B 111.7(19) . . ?
C15 C20 H20A 111.1(17) . . ?
H20B C20 H20A 108(2) . . ?
C15 C20 H20C 111.8(15) . . ?
H20B C20 H20C 109(2) . . ?
H20A C20 H20C 105(2) . . ?
C22 C21 C26 119.7(2) . . ?
C22 C21 P1 121.78(16) . . ?
C26 C21 P1 118.48(16) . . ?
C21 C22 C23 120.1(2) . . ?
C21 C22 H22 120.8(14) . . ?
C23 C22 H22 119.1(14) . . ?
C22 C23 C24 119.8(2) . . ?
C22 C23 H23 122.1(16) . . ?
C24 C23 H23 118.0(16) . . ?
C25 C24 C23 120.9(2) . . ?
C25 C24 H24 118.8(16) . . ?
C23 C24 H24 120.3(16) . . ?
C24 C25 C26 119.6(2) . . ?
C24 C25 H25 120.7(17) . . ?
C26 C25 H25 119.6(17) . . ?
C25 C26 C21 120.0(2) . . ?
C25 C26 H26 122.2(14) . . ?
C21 C26 H26 117.9(14) . . ?
_database_code_depnum_ccdc_archive 'CCDC 981041'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_x1893

_audit_creation_date             2013-10-29T13:55:25-00:00
_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            'C27 H37 O3 P S'
_chemical_formula_weight         472.6
_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                   9.899(5)
_cell_length_b                   13.280(5)
_cell_length_c                   19.567(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_volume                     2572.3(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    23889
_cell_measurement_theta_min      3.302
_cell_measurement_theta_max      32.231

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.22
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.214
_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  0.9538
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      293(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      0.0713664
_diffrn_orient_matrix_ub_12      0.0039489
_diffrn_orient_matrix_ub_13      -0.0017494
_diffrn_orient_matrix_ub_21      0.0034612
_diffrn_orient_matrix_ub_22      0.0004797
_diffrn_orient_matrix_ub_23      0.0362047
_diffrn_orient_matrix_ub_31      0.0053155
_diffrn_orient_matrix_ub_32      -0.0532718
_diffrn_orient_matrix_ub_33      0.0002043
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_number            57680
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.93
_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             7832
_reflns_number_gt                7251
_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)+(0.0406P)²+0.0968P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7832
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0645
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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   -0.01(4)
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   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 0.83373(3) 0.83153(2) 0.505077(14) 0.02501(6) Uani 1 1 d . . .
P1 P 0.88927(3) 0.70046(2) 0.538644(13) 0.01610(5) Uani 1 1 d . . .
O1 O 1.04184(9) 0.72882(8) 0.77118(5) 0.0307(2) Uani 1 1 d . . .
O2 O 0.83392(8) 0.66676(7) 0.76828(4) 0.02272(16) Uani 1 1 d . . .
O3 O 0.61335(8) 0.71811(6) 0.75056(4) 0.01888(15) Uani 1 1 d . . .
C1 C 0.76236(10) 0.70675(8) 0.65464(5) 0.01601(18) Uani 1 1 d . . .
C2 C 0.90676(10) 0.74639(7) 0.66718(5) 0.01645(18) Uani 1 1 d . . .
C3 C 1.00048(10) 0.69308(8) 0.61445(5) 0.01818(19) Uani 1 1 d . . .
C4 C 0.99478(12) 0.58131(8) 0.62749(5) 0.0205(2) Uani 1 1 d . . .
C5 C 0.86951(11) 0.54521(8) 0.61732(5) 0.0198(2) Uani 1 1 d . . .
C6 C 0.77441(10) 0.62888(8) 0.59569(5) 0.01692(18) Uani 1 1 d . . .
C7 C 0.93934(11) 0.71544(8) 0.74001(5) 0.0197(2) Uani 1 1 d . . .
C8 C 0.71776(10) 0.66164(8) 0.72317(5) 0.01762(18) Uani 1 1 d . . .
C9 C 1.12074(16) 0.52544(12) 0.64546(8) 0.0359(3) Uani 1 1 d . . .
C10 C 0.82396(16) 0.43800(9) 0.62210(7) 0.0302(3) Uani 1 1 d . . .
C11 C 0.55006(11) 0.67093(8) 0.80946(5) 0.01769(19) Uani 1 1 d . . .
C12 C 0.50390(11) 0.75327(8) 0.85834(6) 0.0200(2) Uani 1 1 d . . .
C13 C 0.43008(13) 0.70350(11) 0.91860(6) 0.0279(2) Uani 1 1 d . . .
C14 C 0.31240(12) 0.63788(10) 0.89532(6) 0.0265(2) Uani 1 1 d . . .
C15 C 0.36002(11) 0.55695(8) 0.84590(6) 0.0209(2) Uani 1 1 d . . .
C16 C 0.43274(12) 0.60567(8) 0.78565(6) 0.0200(2) Uani 1 1 d . . .
C17 C 0.61802(12) 0.82460(9) 0.88138(6) 0.0251(2) Uani 1 1 d . . .
C18 C 0.72617(15) 0.77363(12) 0.92431(8) 0.0366(3) Uani 1 1 d . . .
C19 C 0.56006(18) 0.91604(13) 0.91875(11) 0.0453(4) Uani 1 1 d . . .
C20 C 0.24216(16) 0.49126(11) 0.82352(7) 0.0315(3) Uani 1 1 d . . .
C21 C 0.95492(11) 0.61817(9) 0.47155(6) 0.0220(2) Uani 1 1 d . . .
C22 C 0.85092(11) 0.59995(8) 0.41671(5) 0.0193(2) Uani 1 1 d . . .
C23 C 0.85731(12) 0.65157(9) 0.35488(6) 0.0234(2) Uani 1 1 d . . .
C24 C 0.76106(13) 0.63438(10) 0.30473(6) 0.0263(2) Uani 1 1 d . . .
C25 C 0.65816(13) 0.56582(9) 0.31536(6) 0.0260(2) Uani 1 1 d . . .
C26 C 0.65015(13) 0.51452(9) 0.37696(7) 0.0270(2) Uani 1 1 d . . .
C27 C 0.74654(13) 0.53162(9) 0.42710(6) 0.0246(2) Uani 1 1 d . . .
H1 H 0.7033(14) 0.7607(10) 0.6418(7) 0.017(3) Uiso 1 1 d . . .
H2 H 0.9138(15) 0.8197(11) 0.6627(7) 0.021(3) Uiso 1 1 d . . .
H3 H 1.0897(15) 0.7235(11) 0.6111(8) 0.024(3) Uiso 1 1 d . . .
H6 H 0.6856(13) 0.6092(9) 0.5773(6) 0.014(3) Uiso 1 1 d . . .
H8 H 0.6919(13) 0.5881(10) 0.7202(7) 0.014(3) Uiso 1 1 d . . .
H9A H 1.164(2) 0.5563(15) 0.6809(11) 0.058(6) Uiso 1 1 d . . .
H9B H 1.191(2) 0.5246(18) 0.6079(13) 0.074(7) Uiso 1 1 d . . .
H9C H 1.107(2) 0.4558(17) 0.6581(11) 0.060(6) Uiso 1 1 d . . .
H10A H 0.7441(19) 0.4320(14) 0.6523(10) 0.044(5) Uiso 1 1 d . . .
H10B H 0.7935(17) 0.4120(13) 0.5770(9) 0.036(4) Uiso 1 1 d . . .
H10C H 0.894(2) 0.3919(17) 0.6398(11) 0.064(6) Uiso 1 1 d . . .
H11 H 0.6169(16) 0.6296(11) 0.8328(7) 0.025(4) Uiso 1 1 d . . .
H12 H 0.4407(15) 0.7962(12) 0.8349(7) 0.023(3) Uiso 1 1 d . . .
H13A H 0.4924(15) 0.6603(11) 0.9440(8) 0.023(3) Uiso 1 1 d . . .
H13B H 0.3962(17) 0.7583(13) 0.9507(9) 0.040(4) Uiso 1 1 d . . .
H14A H 0.2726(17) 0.6023(13) 0.9363(9) 0.037(4) Uiso 1 1 d . . .
H14B H 0.2414(18) 0.6826(13) 0.8748(9) 0.039(4) Uiso 1 1 d . . .
H15 H 0.4218(15) 0.5143(12) 0.8695(8) 0.026(4) Uiso 1 1 d . . .
H16A H 0.4593(14) 0.5510(11) 0.7519(7) 0.024(4) Uiso 1 1 d . . .
H16B H 0.3676(15) 0.6501(12) 0.7609(8) 0.031(4) Uiso 1 1 d . . .
H17 H 0.6608(15) 0.8480(11) 0.8372(7) 0.025(4) Uiso 1 1 d . . .
H18A H 0.6890(17) 0.7495(13) 0.9673(9) 0.040(4) Uiso 1 1 d . . .
H18B H 0.7655(17) 0.7116(14) 0.9049(9) 0.040(4) Uiso 1 1 d . . .
H18C H 0.8043(19) 0.8240(14) 0.9311(9) 0.049(5) Uiso 1 1 d . . .
H19A H 0.514(2) 0.8973(17) 0.9597(12) 0.066(6) Uiso 1 1 d . . .
H19B H 0.626(2) 0.9612(16) 0.9348(10) 0.057(6) Uiso 1 1 d . . .
H19C H 0.495(2) 0.9470(16) 0.8934(11) 0.063(7) Uiso 1 1 d . . .
H20A H 0.168(2) 0.5334(15) 0.8012(10) 0.052(5) Uiso 1 1 d . . .
H20B H 0.2765(18) 0.4421(14) 0.7912(9) 0.040(5) Uiso 1 1 d . . .
H20C H 0.2000(15) 0.4563(11) 0.8625(8) 0.028(4) Uiso 1 1 d . . .
H21A H 1.0348(16) 0.6498(11) 0.4557(8) 0.030(4) Uiso 1 1 d . . .
H21B H 0.9793(14) 0.5516(11) 0.4931(7) 0.025(4) Uiso 1 1 d . . .
H23 H 0.9279(16) 0.6981(12) 0.3474(7) 0.027(4) Uiso 1 1 d . . .
H24 H 0.7649(14) 0.6681(11) 0.2629(8) 0.024(3) Uiso 1 1 d . . .
H25 H 0.5966(17) 0.5539(12) 0.2801(9) 0.035(4) Uiso 1 1 d . . .
H26 H 0.5836(15) 0.4657(11) 0.3817(8) 0.025(4) Uiso 1 1 d . . .
H27 H 0.7432(17) 0.4936(12) 0.4712(9) 0.034(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 1.9400(7) . ?
P1 C21 1.8276(12) . ?
P1 C3 1.8497(11) . ?
P1 C6 1.8553(11) . ?
O1 C7 1.1971(14) . ?
O2 C7 1.3464(14) . ?
O2 C8 1.4513(14) . ?
O3 C8 1.3849(13) . ?
O3 C11 1.4537(12) . ?
C1 C8 1.5335(14) . ?
C1 C2 1.5429(16) . ?
C1 C6 1.5538(15) . ?
C1 H1 0.958(14) . ?
C2 C7 1.5178(15) . ?
C2 C3 1.5577(15) . ?
C2 H2 0.980(15) . ?
C3 C4 1.5071(16) . ?
C3 H3 0.973(15) . ?
C4 C5 1.3444(17) . ?
C4 C9 1.4929(18) . ?
C5 C10 1.4963(17) . ?
C5 C6 1.5165(15) . ?
C6 H6 0.986(13) . ?
C8 H8 1.011(13) . ?
C9 H9A 0.91(2) . ?
C9 H9B 1.01(2) . ?
C9 H9C 0.97(2) . ?
C10 H10A 0.990(19) . ?
C10 H10B 0.994(17) . ?
C10 H10C 0.99(2) . ?
C11 C16 1.5221(16) . ?
C11 C12 1.5229(15) . ?
C11 H11 0.974(15) . ?
C12 C13 1.5366(16) . ?
C12 C17 1.5416(16) . ?
C12 H12 0.963(15) . ?
C13 C14 1.5244(17) . ?
C13 H13A 0.978(15) . ?
C13 H13B 1.018(17) . ?
C14 C15 1.5206(17) . ?
C14 H14A 1.011(17) . ?
C14 H14B 1.004(18) . ?
C15 C20 1.5212(18) . ?
C15 C16 1.5253(15) . ?
C15 H15 0.953(16) . ?
C16 H16A 1.016(14) . ?
C16 H16B 0.999(16) . ?
C17 C18 1.520(2) . ?
C17 C19 1.5293(19) . ?
C17 H17 1.011(15) . ?
C18 H18A 0.973(19) . ?
C18 H18B 0.988(18) . ?
C18 H18C 1.03(2) . ?
C19 H19A 0.96(2) . ?
C19 H19B 0.94(2) . ?
C19 H19C 0.91(2) . ?
C20 H20A 1.02(2) . ?
C20 H20B 0.970(18) . ?
C20 H20C 0.985(16) . ?
C21 C22 1.5065(16) . ?
C21 H21A 0.948(15) . ?
C21 H21B 1.009(14) . ?
C22 C27 1.3901(17) . ?
C22 C23 1.3921(16) . ?
C23 C24 1.3867(17) . ?
C23 H23 0.944(16) . ?
C24 C25 1.3819(19) . ?
C24 H24 0.933(15) . ?
C25 C26 1.3868(19) . ?
C25 H25 0.934(17) . ?
C26 C27 1.3872(18) . ?
C26 H26 0.929(15) . ?
C27 H27 1.001(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
C21 P1 C3 109.44(5) . . ?
C21 P1 C6 110.10(6) . . ?
C3 P1 C6 81.67(5) . . ?
C21 P1 S1 113.21(4) . . ?
C3 P1 S1 119.19(4) . . ?
C6 P1 S1 119.32(4) . . ?
C7 O2 C8 112.75(8) . . ?
C8 O3 C11 113.27(8) . . ?
C8 C1 C2 105.13(8) . . ?
C8 C1 C6 114.28(9) . . ?
C2 C1 C6 105.90(8) . . ?
C8 C1 H1 110.2(8) . . ?
C2 C1 H1 110.6(8) . . ?
C6 C1 H1 110.5(8) . . ?
C7 C2 C1 104.70(8) . . ?
C7 C2 C3 111.86(9) . . ?
C1 C2 C3 106.94(8) . . ?
C7 C2 H2 109.8(8) . . ?
C1 C2 H2 113.0(9) . . ?
C3 C2 H2 110.5(8) . . ?
C4 C3 C2 108.25(9) . . ?
C4 C3 P1 99.54(7) . . ?
C2 C3 P1 98.78(7) . . ?
C4 C3 H3 117.0(9) . . ?
C2 C3 H3 113.3(9) . . ?
P1 C3 H3 117.6(9) . . ?
C5 C4 C9 128.90(12) . . ?
C5 C4 C3 111.14(9) . . ?
C9 C4 C3 119.88(12) . . ?
C4 C5 C10 127.45(11) . . ?
C4 C5 C6 110.64(10) . . ?
C10 C5 C6 121.84(11) . . ?
C5 C6 C1 109.16(9) . . ?
C5 C6 P1 99.38(7) . . ?
C1 C6 P1 98.78(7) . . ?
C5 C6 H6 117.5(7) . . ?
C1 C6 H6 112.3(7) . . ?
P1 C6 H6 117.6(7) . . ?
O1 C7 O2 121.26(10) . . ?
O1 C7 C2 128.18(10) . . ?
O2 C7 C2 110.55(9) . . ?
O3 C8 O2 109.29(9) . . ?
O3 C8 C1 109.99(9) . . ?
O2 C8 C1 106.58(8) . . ?
O3 C8 H8 110.8(7) . . ?
O2 C8 H8 106.3(8) . . ?
C1 C8 H8 113.6(7) . . ?
C4 C9 H9A 110.6(13) . . ?
C4 C9 H9B 114.2(13) . . ?
H9A C9 H9B 103.2(18) . . ?
C4 C9 H9C 114.7(13) . . ?
H9A C9 H9C 107.5(17) . . ?
H9B C9 H9C 105.8(18) . . ?
C5 C10 H10A 110.7(11) . . ?
C5 C10 H10B 111.4(10) . . ?
H10A C10 H10B 105.0(14) . . ?
C5 C10 H10C 113.5(13) . . ?
H10A C10 H10C 107.7(16) . . ?
H10B C10 H10C 108.0(16) . . ?
O3 C11 C16 109.37(8) . . ?
O3 C11 C12 108.52(9) . . ?
C16 C11 C12 111.85(9) . . ?
O3 C11 H11 108.8(9) . . ?
C16 C11 H11 109.9(9) . . ?
C12 C11 H11 108.3(9) . . ?
C11 C12 C13 108.41(10) . . ?
C11 C12 C17 113.89(9) . . ?
C13 C12 C17 112.86(9) . . ?
C11 C12 H12 108.7(9) . . ?
C13 C12 H12 108.2(9) . . ?
C17 C12 H12 104.6(9) . . ?
C14 C13 C12 112.33(10) . . ?
C14 C13 H13A 107.4(9) . . ?
C12 C13 H13A 110.0(9) . . ?
C14 C13 H13B 110.0(10) . . ?
C12 C13 H13B 108.8(10) . . ?
H13A C13 H13B 108.3(13) . . ?
C15 C14 C13 110.92(10) . . ?
C15 C14 H14A 107.1(9) . . ?
C13 C14 H14A 109.2(10) . . ?
C15 C14 H14B 112.4(10) . . ?
C13 C14 H14B 108.4(10) . . ?
H14A C14 H14B 108.7(14) . . ?
C14 C15 C20 110.52(10) . . ?
C14 C15 C16 109.76(10) . . ?
C20 C15 C16 112.50(10) . . ?
C14 C15 H15 108.1(9) . . ?
C20 C15 H15 106.9(9) . . ?
C16 C15 H15 108.9(9) . . ?
C11 C16 C15 111.41(9) . . ?
C11 C16 H16A 114.1(8) . . ?
C15 C16 H16A 108.7(8) . . ?
C11 C16 H16B 107.7(9) . . ?
C15 C16 H16B 108.7(9) . . ?
H16A C16 H16B 105.9(12) . . ?
C18 C17 C19 110.70(13) . . ?
C18 C17 C12 113.84(11) . . ?
C19 C17 C12 110.66(11) . . ?
C18 C17 H17 108.3(9) . . ?
C19 C17 H17 108.8(8) . . ?
C12 C17 H17 104.2(8) . . ?
C17 C18 H18A 111.0(10) . . ?
C17 C18 H18B 115.9(10) . . ?
H18A C18 H18B 102.0(15) . . ?
C17 C18 H18C 108.1(10) . . ?
H18A C18 H18C 112.7(14) . . ?
H18B C18 H18C 107.1(14) . . ?
C17 C19 H19A 112.0(13) . . ?
C17 C19 H19B 113.9(12) . . ?
H19A C19 H19B 102.7(17) . . ?
C17 C19 H19C 111.3(14) . . ?
H19A C19 H19C 103.6(18) . . ?
H19B C19 H19C 112.6(18) . . ?
C15 C20 H20A 111.2(11) . . ?
C15 C20 H20B 107.8(11) . . ?
H20A C20 H20B 110.0(15) . . ?
C15 C20 H20C 111.9(9) . . ?
H20A C20 H20C 106.4(14) . . ?
H20B C20 H20C 109.6(14) . . ?
C22 C21 P1 111.39(8) . . ?
C22 C21 H21A 114.1(10) . . ?
P1 C21 H21A 105.4(9) . . ?
C22 C21 H21B 108.7(8) . . ?
P1 C21 H21B 107.9(8) . . ?
H21A C21 H21B 109.0(12) . . ?
C27 C22 C23 118.84(10) . . ?
C27 C22 C21 120.58(10) . . ?
C23 C22 C21 120.59(10) . . ?
C24 C23 C22 120.18(11) . . ?
C24 C23 H23 120.5(9) . . ?
C22 C23 H23 119.3(9) . . ?
C25 C24 C23 120.56(11) . . ?
C25 C24 H24 118.5(9) . . ?
C23 C24 H24 120.9(9) . . ?
C24 C25 C26 119.77(11) . . ?
C24 C25 H25 118.8(10) . . ?
C26 C25 H25 121.4(10) . . ?
C25 C26 C27 119.67(12) . . ?
C25 C26 H26 118.0(9) . . ?
C27 C26 H26 122.1(9) . . ?
C26 C27 C22 120.98(11) . . ?
C26 C27 H27 120.3(10) . . ?
C22 C27 H27 118.7(10) . . ?
_database_code_depnum_ccdc_archive 'CCDC 981042'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_x1657

_audit_creation_date             2013-06-11T14:43:07-00:00
_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            'C26 H36 N O3 P S'
_chemical_formula_weight         473.59
_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                   9.9928(2)
_cell_length_b                   13.3160(2)
_cell_length_c                   19.1769(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2551.76(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    15073
_cell_measurement_theta_min      2.9383
_cell_measurement_theta_max      32.6369

#----------------------------------------------------------------------------#
#                   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    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.216
_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  0.98635
_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      -0.0573981
_diffrn_orient_matrix_ub_12      0.0172017
_diffrn_orient_matrix_ub_13      -0.0181849
_diffrn_orient_matrix_ub_21      -0.0346606
_diffrn_orient_matrix_ub_22      0.0053016
_diffrn_orient_matrix_ub_23      0.0320809
_diffrn_orient_matrix_ub_31      0.0233181
_diffrn_orient_matrix_ub_32      0.0501255
_diffrn_orient_matrix_ub_33      0.0028597
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_number            51223
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.94
_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             7775
_reflns_number_gt                6951
_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)+(0.0338P)²+0.2843P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7775
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.044
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0743
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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   -0.01(5)
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   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'
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
S1 S 0.16136(4) 0.16504(3) 0.50126(2) 0.02949(9) Uani 1 1 d . . .
P1 P 0.10970(4) 0.29786(3) 0.533149(17) 0.01847(7) Uani 1 1 d . . .
O1 O -0.03363(12) 0.28012(10) 0.77191(6) 0.0357(3) Uani 1 1 d . . .
O2 O 0.17233(10) 0.34212(8) 0.76567(5) 0.0252(2) Uani 1 1 d . . .
O3 O 0.38937(10) 0.28818(7) 0.74665(5) 0.02024(19) Uani 1 1 d . . .
N1 N 0.24494(14) 0.46026(10) 0.42741(7) 0.0288(3) Uani 1 1 d . . .
C1 C 0.23948(13) 0.29685(11) 0.65020(6) 0.0174(2) Uani 1 1 d . . .
C2 C 0.09633(14) 0.25851(10) 0.66511(7) 0.0182(3) Uani 1 1 d . . .
C3 C 0.00284(14) 0.31039(10) 0.61133(7) 0.0196(3) Uani 1 1 d . . .
C4 C 0.01105(15) 0.42252(11) 0.62144(7) 0.0215(3) Uani 1 1 d . . .
C5 C 0.13451(15) 0.45634(10) 0.60848(7) 0.0215(3) Uani 1 1 d . . .
C6 C 0.22681(14) 0.37095(11) 0.58801(7) 0.0189(3) Uani 1 1 d . . .
C7 C 0.06703(14) 0.29245(12) 0.73879(7) 0.0228(3) Uani 1 1 d . . .
C8 C 0.28587(13) 0.34482(10) 0.71848(7) 0.0188(3) Uani 1 1 d . . .
C9 C -0.1118(2) 0.48106(16) 0.63881(10) 0.0374(4) Uani 1 1 d . . .
C10 C 0.1823(2) 0.56295(12) 0.60674(10) 0.0344(4) Uani 1 1 d . . .
C11 C 0.45219(14) 0.33480(11) 0.80688(7) 0.0192(3) Uani 1 1 d . . .
C12 C 0.49601(14) 0.25204(11) 0.85679(7) 0.0209(3) Uani 1 1 d . . .
C13 C 0.56972(17) 0.30063(14) 0.91840(8) 0.0299(3) Uani 1 1 d . . .
C14 C 0.68730(17) 0.36485(13) 0.89514(9) 0.0290(3) Uani 1 1 d . . .
C15 C 0.64311(15) 0.44616(11) 0.84430(7) 0.0228(3) Uani 1 1 d . . .
C16 C 0.57003(15) 0.39837(11) 0.78298(7) 0.0216(3) Uani 1 1 d . . .
C17 C 0.38126(15) 0.18231(11) 0.87983(8) 0.0257(3) Uani 1 1 d . . .
C18 C 0.2772(2) 0.23398(16) 0.92512(10) 0.0388(4) Uani 1 1 d . . .
C19 C 0.4365(2) 0.08917(16) 0.91615(13) 0.0445(5) Uani 1 1 d . . .
C20 C 0.7615(2) 0.50960(14) 0.82176(9) 0.0343(4) Uani 1 1 d . . .
C21 C 0.04335(15) 0.37658(12) 0.46353(8) 0.0240(3) Uani 1 1 d . . .
C22 C 0.14909(15) 0.39492(11) 0.40923(7) 0.0213(3) Uani 1 1 d . . .
C23 C 0.14707(16) 0.34616(12) 0.34530(7) 0.0259(3) Uani 1 1 d . . .
C24 C 0.24870(17) 0.36510(13) 0.29837(8) 0.0306(3) Uani 1 1 d . . .
C25 C 0.34763(18) 0.43262(12) 0.31603(8) 0.0301(3) Uani 1 1 d . . .
C26 C 0.34180(18) 0.47769(13) 0.38091(9) 0.0317(3) Uani 1 1 d . . .
H1 H 0.2972(16) 0.2424(12) 0.6390(8) 0.015(4) Uiso 1 1 d . . .
H2 H 0.0872(16) 0.1856(12) 0.6626(8) 0.020(4) Uiso 1 1 d . . .
H3 H -0.0819(19) 0.2804(14) 0.6117(10) 0.033(5) Uiso 1 1 d . . .
H6 H 0.3108(19) 0.3882(13) 0.5693(9) 0.030(5) Uiso 1 1 d . . .
H8 H 0.3113(15) 0.4176(12) 0.7146(8) 0.016(4) Uiso 1 1 d . . .
H9A H -0.094(2) 0.5496(18) 0.6514(11) 0.049(6) Uiso 1 1 d . . .
H9B H -0.177(3) 0.4831(18) 0.6024(14) 0.064(7) Uiso 1 1 d . . .
H9C H -0.153(3) 0.4546(17) 0.6759(13) 0.060(7) Uiso 1 1 d . . .
H10A H 0.214(2) 0.5825(14) 0.5590(11) 0.039(5) Uiso 1 1 d . . .
H10B H 0.259(2) 0.5719(16) 0.6377(12) 0.052(6) Uiso 1 1 d . . .
H10C H 0.115(3) 0.6126(19) 0.6190(12) 0.066(7) Uiso 1 1 d . . .
H11 H 0.3869(18) 0.3812(13) 0.8297(9) 0.027(4) Uiso 1 1 d . . .
H12 H 0.5603(17) 0.2098(13) 0.8299(9) 0.028(4) Uiso 1 1 d . . .
H13A H 0.5112(18) 0.3440(13) 0.9435(9) 0.025(4) Uiso 1 1 d . . .
H13B H 0.600(2) 0.2477(15) 0.9509(11) 0.044(5) Uiso 1 1 d . . .
H14A H 0.729(2) 0.3990(14) 0.9400(10) 0.038(5) Uiso 1 1 d . . .
H14B H 0.755(2) 0.3212(17) 0.8729(11) 0.051(6) Uiso 1 1 d . . .
H15 H 0.5783(18) 0.4919(13) 0.8680(9) 0.023(4) Uiso 1 1 d . . .
H16A H 0.5446(17) 0.4521(13) 0.7492(9) 0.028(5) Uiso 1 1 d . . .
H16B H 0.6298(19) 0.3587(14) 0.7571(10) 0.037(5) Uiso 1 1 d . . .
H17 H 0.3355(18) 0.1598(13) 0.8358(9) 0.029(4) Uiso 1 1 d . . .
H18A H 0.241(2) 0.2954(17) 0.9034(11) 0.047(6) Uiso 1 1 d . . .
H18B H 0.204(2) 0.1863(17) 0.9313(11) 0.058(7) Uiso 1 1 d . . .
H18C H 0.313(2) 0.2504(18) 0.9703(13) 0.059(7) Uiso 1 1 d . . .
H19A H 0.369(2) 0.0439(17) 0.9293(11) 0.055(6) Uiso 1 1 d . . .
H19B H 0.501(2) 0.0548(17) 0.8869(12) 0.054(7) Uiso 1 1 d . . .
H19C H 0.480(2) 0.1095(18) 0.9566(13) 0.060(7) Uiso 1 1 d . . .
H20A H 0.828(2) 0.4681(17) 0.7981(11) 0.049(6) Uiso 1 1 d . . .
H20B H 0.730(2) 0.5622(16) 0.7897(11) 0.045(6) Uiso 1 1 d . . .
H20C H 0.802(2) 0.5463(14) 0.8630(10) 0.038(5) Uiso 1 1 d . . .
H21A H 0.0143(16) 0.4410(13) 0.4831(8) 0.023(4) Uiso 1 1 d . . .
H21B H -0.0301(18) 0.3444(13) 0.4462(9) 0.028(5) Uiso 1 1 d . . .
H23 H 0.0784(17) 0.3009(13) 0.3357(9) 0.025(4) Uiso 1 1 d . . .
H24 H 0.2495(19) 0.3308(15) 0.2519(10) 0.038(5) Uiso 1 1 d . . .
H25 H 0.417(2) 0.4477(15) 0.2847(11) 0.046(6) Uiso 1 1 d . . .
H26 H 0.404(2) 0.5225(15) 0.3938(10) 0.036(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 1.9414(5) . ?
P1 C21 1.8222(15) . ?
P1 C3 1.8482(14) . ?
P1 C6 1.8503(14) . ?
O1 C7 1.2009(17) . ?
O2 C7 1.3455(18) . ?
O2 C8 1.4517(17) . ?
O3 C8 1.3894(16) . ?
O3 C11 1.4538(15) . ?
N1 C26 1.336(2) . ?
N1 C22 1.340(2) . ?
C1 C8 1.5289(18) . ?
C1 C2 1.5456(19) . ?
C1 C6 1.5530(19) . ?
C1 H1 0.951(16) . ?
C2 C7 1.5120(19) . ?
C2 C3 1.5537(19) . ?
C2 H2 0.976(16) . ?
C3 C4 1.508(2) . ?
C3 H3 0.936(19) . ?
C4 C5 1.337(2) . ?
C4 C9 1.492(2) . ?
C5 C10 1.498(2) . ?
C5 C6 1.516(2) . ?
C6 H6 0.941(19) . ?
C8 H8 1.005(16) . ?
C9 H9A 0.96(2) . ?
C9 H9B 0.95(3) . ?
C9 H9C 0.89(2) . ?
C10 H10A 1.00(2) . ?
C10 H10B 0.98(2) . ?
C10 H10C 0.97(3) . ?
C11 C16 1.521(2) . ?
C11 C12 1.5240(19) . ?
C11 H11 0.999(18) . ?
C12 C13 1.535(2) . ?
C12 C17 1.540(2) . ?
C12 H12 0.997(18) . ?
C13 C14 1.520(2) . ?
C13 H13A 0.953(18) . ?
C13 H13B 0.99(2) . ?
C14 C15 1.523(2) . ?
C14 H14A 1.06(2) . ?
C14 H14B 0.99(2) . ?
C15 C20 1.517(2) . ?
C15 C16 1.5234(19) . ?
C15 H15 0.998(18) . ?
C16 H16A 0.998(17) . ?
C16 H16B 0.94(2) . ?
C17 C18 1.520(2) . ?
C17 C19 1.526(2) . ?
C17 H17 1.007(18) . ?
C18 H18A 0.99(2) . ?
C18 H18B 0.98(2) . ?
C18 H18C 0.96(2) . ?
C19 H19A 0.94(2) . ?
C19 H19B 0.97(2) . ?
C19 H19C 0.93(3) . ?
C20 H20A 0.98(2) . ?
C20 H20B 0.99(2) . ?
C20 H20C 1.01(2) . ?
C21 C22 1.503(2) . ?
C21 H21A 0.980(17) . ?
C21 H21B 0.912(18) . ?
C22 C23 1.3874(19) . ?
C23 C24 1.380(2) . ?
C23 H23 0.932(18) . ?
C24 C25 1.379(3) . ?
C24 H24 1.001(19) . ?
C25 C26 1.383(2) . ?
C25 H25 0.94(2) . ?
C26 H26 0.89(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
C21 P1 C3 109.41(7) . . ?
C21 P1 C6 110.13(7) . . ?
C3 P1 C6 81.76(6) . . ?
C21 P1 S1 112.95(5) . . ?
C3 P1 S1 119.43(5) . . ?
C6 P1 S1 119.35(5) . . ?
C7 O2 C8 112.62(10) . . ?
C8 O3 C11 113.49(10) . . ?
C26 N1 C22 117.18(14) . . ?
C8 C1 C2 105.08(10) . . ?
C8 C1 C6 114.64(12) . . ?
C2 C1 C6 106.05(10) . . ?
C8 C1 H1 109.2(9) . . ?
C2 C1 H1 110.6(9) . . ?
C6 C1 H1 111.1(9) . . ?
C7 C2 C1 104.68(11) . . ?
C7 C2 C3 111.77(11) . . ?
C1 C2 C3 106.67(11) . . ?
C7 C2 H2 109.0(9) . . ?
C1 C2 H2 114.0(10) . . ?
C3 C2 H2 110.6(10) . . ?
C4 C3 C2 108.80(11) . . ?
C4 C3 P1 99.33(9) . . ?
C2 C3 P1 98.68(9) . . ?
C4 C3 H3 118.0(11) . . ?
C2 C3 H3 110.4(12) . . ?
P1 C3 H3 119.4(11) . . ?
C5 C4 C9 128.69(15) . . ?
C5 C4 C3 111.10(12) . . ?
C9 C4 C3 120.08(15) . . ?
C4 C5 C10 128.14(14) . . ?
C4 C5 C6 110.92(12) . . ?
C10 C5 C6 120.73(14) . . ?
C5 C6 C1 109.11(11) . . ?
C5 C6 P1 99.03(9) . . ?
C1 C6 P1 98.86(9) . . ?
C5 C6 H6 117.3(11) . . ?
C1 C6 H6 112.0(11) . . ?
P1 C6 H6 118.4(11) . . ?
O1 C7 O2 121.31(13) . . ?
O1 C7 C2 127.99(14) . . ?
O2 C7 C2 110.70(12) . . ?
O3 C8 O2 109.02(10) . . ?
O3 C8 C1 109.38(11) . . ?
O2 C8 C1 106.65(10) . . ?
O3 C8 H8 111.4(9) . . ?
O2 C8 H8 105.5(9) . . ?
C1 C8 H8 114.6(9) . . ?
C4 C9 H9A 113.7(14) . . ?
C4 C9 H9B 114.3(15) . . ?
H9A C9 H9B 106.3(19) . . ?
C4 C9 H9C 110.6(16) . . ?
H9A C9 H9C 105.1(19) . . ?
H9B C9 H9C 106(2) . . ?
C5 C10 H10A 111.5(11) . . ?
C5 C10 H10B 110.6(13) . . ?
H10A C10 H10B 106.0(17) . . ?
C5 C10 H10C 114.7(15) . . ?
H10A C10 H10C 105.2(18) . . ?
H10B C10 H10C 108.2(18) . . ?
O3 C11 C16 109.43(10) . . ?
O3 C11 C12 108.32(11) . . ?
C16 C11 C12 111.67(11) . . ?
O3 C11 H11 109.3(10) . . ?
C16 C11 H11 107.1(10) . . ?
C12 C11 H11 111.0(10) . . ?
C11 C12 C13 108.44(12) . . ?
C11 C12 C17 113.72(12) . . ?
C13 C12 C17 112.99(12) . . ?
C11 C12 H12 105.6(10) . . ?
C13 C12 H12 109.0(10) . . ?
C17 C12 H12 106.7(10) . . ?
C14 C13 C12 112.47(12) . . ?
C14 C13 H13A 106.4(11) . . ?
C12 C13 H13A 110.5(10) . . ?
C14 C13 H13B 110.2(12) . . ?
C12 C13 H13B 109.5(12) . . ?
H13A C13 H13B 107.6(15) . . ?
C13 C14 C15 111.33(13) . . ?
C13 C14 H14A 108.1(11) . . ?
C15 C14 H14A 109.2(10) . . ?
C13 C14 H14B 109.1(13) . . ?
C15 C14 H14B 109.9(12) . . ?
H14A C14 H14B 109.1(16) . . ?
C20 C15 C14 110.62(14) . . ?
C20 C15 C16 112.75(13) . . ?
C14 C15 C16 109.65(12) . . ?
C20 C15 H15 107.2(10) . . ?
C14 C15 H15 109.3(10) . . ?
C16 C15 H15 107.1(10) . . ?
C11 C16 C15 111.78(11) . . ?
C11 C16 H16A 113.4(10) . . ?
C15 C16 H16A 108.9(10) . . ?
C11 C16 H16B 109.8(12) . . ?
C15 C16 H16B 109.8(11) . . ?
H16A C16 H16B 102.9(14) . . ?
C18 C17 C19 110.78(16) . . ?
C18 C17 C12 113.61(13) . . ?
C19 C17 C12 110.57(13) . . ?
C18 C17 H17 107.7(10) . . ?
C19 C17 H17 107.8(10) . . ?
C12 C17 H17 106.1(10) . . ?
C17 C18 H18A 112.6(12) . . ?
C17 C18 H18B 106.8(13) . . ?
H18A C18 H18B 108.5(17) . . ?
C17 C18 H18C 111.2(14) . . ?
H18A C18 H18C 109.2(19) . . ?
H18B C18 H18C 108.6(19) . . ?
C17 C19 H19A 112.5(14) . . ?
C17 C19 H19B 111.1(13) . . ?
H19A C19 H19B 109.2(19) . . ?
C17 C19 H19C 108.2(15) . . ?
H19A C19 H19C 107.3(19) . . ?
H19B C19 H19C 108.3(19) . . ?
C15 C20 H20A 110.4(13) . . ?
C15 C20 H20B 108.7(13) . . ?
H20A C20 H20B 109.5(17) . . ?
C15 C20 H20C 110.9(11) . . ?
H20A C20 H20C 111.4(17) . . ?
H20B C20 H20C 105.8(16) . . ?
C22 C21 P1 110.20(10) . . ?
C22 C21 H21A 109.4(10) . . ?
P1 C21 H21A 109.3(9) . . ?
C22 C21 H21B 112.9(11) . . ?
P1 C21 H21B 106.8(11) . . ?
H21A C21 H21B 108.2(14) . . ?
N1 C22 C23 122.96(14) . . ?
N1 C22 C21 115.32(13) . . ?
C23 C22 C21 121.72(14) . . ?
C24 C23 C22 118.69(15) . . ?
C24 C23 H23 122.1(11) . . ?
C22 C23 H23 119.2(11) . . ?
C25 C24 C23 119.11(15) . . ?
C25 C24 H24 120.7(11) . . ?
C23 C24 H24 120.2(11) . . ?
C24 C25 C26 118.30(16) . . ?
C24 C25 H25 120.8(13) . . ?
C26 C25 H25 121.0(13) . . ?
N1 C26 C25 123.75(16) . . ?
N1 C26 H26 115.6(13) . . ?
C25 C26 H26 120.7(13) . . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 981043'
