# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_gf50m2
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H27 F N O2 P S'
_chemical_formula_weight         347.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P21212

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                   34.891(4)
_cell_length_b                   6.7332(7)
_cell_length_c                   7.8957(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1854.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6948
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.61

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8744
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10363
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4198
_reflns_number_gt                4016
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0560P)²+0.3109P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_number_reflns         4198
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.186
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.85133(5) 0.0973(3) 1.0923(2) 0.0240(4) Uani 1 1 d . . .
H1A H 0.8687 0.0254 1.1682 0.029 Uiso 1 1 calc R . .
C2 C 0.81493(5) 0.1500(3) 1.1894(2) 0.0253(4) Uani 1 1 d . . .
H2A H 0.7978 0.2185 1.1101 0.030 Uiso 1 1 calc R . .
C3 C 0.79525(6) -0.0461(3) 1.2388(3) 0.0339(4) Uani 1 1 d . . .
H3A H 0.8115 -0.1179 1.3173 0.041 Uiso 1 1 calc R . .
H3B H 0.7713 -0.0169 1.2961 0.041 Uiso 1 1 calc R . .
C4 C 0.78714(6) -0.1770(3) 1.0853(3) 0.0365(5) Uani 1 1 d . . .
H4A H 0.7692 -0.1096 1.0110 0.044 Uiso 1 1 calc R . .
H4B H 0.7753 -0.2998 1.1226 0.044 Uiso 1 1 calc R . .
C5 C 0.82382(6) -0.2246(3) 0.9868(3) 0.0328(4) Uani 1 1 d . . .
H5A H 0.8411 -0.2983 1.0620 0.039 Uiso 1 1 calc R . .
C6 C 0.84344(6) -0.0307(3) 0.9380(3) 0.0314(4) Uani 1 1 d . . .
H6A H 0.8674 -0.0599 0.8810 0.038 Uiso 1 1 calc R . .
H6B H 0.8272 0.0419 0.8597 0.038 Uiso 1 1 calc R . .
O1 O 0.86944(4) 0.2829(2) 1.04202(18) 0.0319(3) Uani 1 1 d . . .
P1 P 0.913178(13) 0.29848(8) 0.99146(6) 0.02869(12) Uani 1 1 d . . .
S1 S 0.946644(15) 0.12364(11) 1.12082(7) 0.04393(16) Uani 1 1 d . . .
F1 F 0.91895(4) 0.5189(2) 1.0508(2) 0.0546(4) Uani 1 1 d . . .
O2 O 0.91817(4) 0.3016(3) 0.80445(18) 0.0385(4) Uani 1 1 d . . .
C7 C 0.82217(6) 0.2925(3) 1.3385(2) 0.0321(4) Uani 1 1 d . . .
H7A H 0.8344 0.4114 1.2914 0.039 Uiso 1 1 calc R . .
C8 C 0.78435(7) 0.3598(4) 1.4186(3) 0.0495(6) Uani 1 1 d . . .
H8A H 0.7673 0.4055 1.3316 0.074 Uiso 1 1 calc R . .
H8B H 0.7892 0.4658 1.4970 0.074 Uiso 1 1 calc R . .
H8C H 0.7728 0.2503 1.4775 0.074 Uiso 1 1 calc R . .
C9 C 0.84942(8) 0.2097(4) 1.4723(3) 0.0479(6) Uani 1 1 d . . .
H9A H 0.8517 0.3030 1.5637 0.072 Uiso 1 1 calc R . .
H9B H 0.8742 0.1876 1.4225 0.072 Uiso 1 1 calc R . .
H9C H 0.8395 0.0864 1.5148 0.072 Uiso 1 1 calc R . .
C10 C 0.81578(7) -0.3535(4) 0.8314(3) 0.0486(6) Uani 1 1 d . . .
H10A H 0.8015 -0.2780 0.7498 0.073 Uiso 1 1 calc R . .
H10B H 0.8012 -0.4679 0.8647 0.073 Uiso 1 1 calc R . .
H10C H 0.8396 -0.3956 0.7822 0.073 Uiso 1 1 calc R . .
N1 N 0.98624(4) 0.2469(2) 0.6785(2) 0.0282(3) Uani 1 1 d . . .
H1B H 0.9640 0.2452 0.7254 0.034 Uiso 1 1 calc R . .
C11 C 0.98884(5) 0.2538(3) 0.5099(3) 0.0295(4) Uani 1 1 d . . .
H11A H 0.9666 0.2543 0.4448 0.035 Uiso 1 1 calc R . .
C12 C 1.02400(6) 0.2603(3) 0.4316(3) 0.0320(4) Uani 1 1 d . . .
H12A H 1.0256 0.2635 0.3141 0.038 Uiso 1 1 calc R . .
C13 C 1.05729(5) 0.2620(3) 0.5294(3) 0.0297(4) Uani 1 1 d . . .
C14 C 1.05339(6) 0.2488(3) 0.7042(3) 0.0333(4) Uani 1 1 d . . .
H14A H 1.0751 0.2443 0.7726 0.040 Uiso 1 1 calc R . .
C15 C 1.01764(6) 0.2425(3) 0.7758(3) 0.0345(4) Uani 1 1 d . . .
H15A H 1.0152 0.2351 0.8929 0.041 Uiso 1 1 calc R . .
C16 C 1.09580(7) 0.2838(4) 0.4474(4) 0.0501(6) Uani 1 1 d . . .
H16A H 1.1014 0.4221 0.4320 0.075 Uiso 1 1 calc R . .
H16B H 1.0956 0.2184 0.3393 0.075 Uiso 1 1 calc R . .
H16C H 1.1150 0.2246 0.5184 0.075 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.455(2) . ?
C1 C6 1.518(3) . ?
C1 C2 1.525(2) . ?
C1 H1A 0.9800 . ?
C2 C3 1.538(3) . ?
C2 C7 1.540(3) . ?
C2 H2A 0.9800 . ?
C3 C4 1.525(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.531(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.523(3) . ?
C5 C10 1.529(3) . ?
C5 H5A 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O1 P1 1.5809(14) . ?
P1 O2 1.4869(14) . ?
P1 F1 1.5694(15) . ?
P1 S1 1.9475(8) . ?
C7 C9 1.527(3) . ?
C7 C8 1.532(3) . ?
C7 H7A 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 C11 1.335(3) . ?
N1 C15 1.339(3) . ?
N1 H1B 0.8600 . ?
C11 C12 1.374(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.395(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.390(3) . ?
C13 C16 1.499(3) . ?
C14 C15 1.370(3) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 110.33(15) . . ?
O1 C1 C2 107.39(14) . . ?
C6 C1 C2 112.61(15) . . ?
O1 C1 H1A 108.8 . . ?
C6 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
C1 C2 C3 107.42(15) . . ?
C1 C2 C7 113.12(15) . . ?
C3 C2 C7 114.47(16) . . ?
C1 C2 H2A 107.1 . . ?
C3 C2 H2A 107.1 . . ?
C7 C2 H2A 107.1 . . ?
C4 C3 C2 112.15(17) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 C5 111.69(16) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C10 111.45(19) . . ?
C6 C5 C4 108.93(17) . . ?
C10 C5 C4 111.90(17) . . ?
C6 C5 H5A 108.1 . . ?
C10 C5 H5A 108.1 . . ?
C4 C5 H5A 108.1 . . ?
C1 C6 C5 111.40(16) . . ?
C1 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C1 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C1 O1 P1 123.04(11) . . ?
O2 P1 F1 105.57(10) . . ?
O2 P1 O1 111.39(8) . . ?
F1 P1 O1 96.39(8) . . ?
O2 P1 S1 117.33(7) . . ?
F1 P1 S1 109.76(7) . . ?
O1 P1 S1 113.96(6) . . ?
C9 C7 C8 111.04(19) . . ?
C9 C7 C2 113.79(18) . . ?
C8 C7 C2 111.02(17) . . ?
C9 C7 H7A 106.9 . . ?
C8 C7 H7A 106.9 . . ?
C2 C7 H7A 106.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 N1 C15 121.18(16) . . ?
C11 N1 H1B 119.4 . . ?
C15 N1 H1B 119.4 . . ?
N1 C11 C12 120.68(18) . . ?
N1 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C13 119.64(18) . . ?
C11 C12 H12A 120.2 . . ?
C13 C12 H12A 120.2 . . ?
C14 C13 C12 117.89(19) . . ?
C14 C13 C16 121.5(2) . . ?
C12 C13 C16 120.56(19) . . ?
C15 C14 C13 120.07(19) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
N1 C15 C14 120.48(18) . . ?
N1 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.63(15) . . . . ?
C6 C1 C2 C3 57.0(2) . . . . ?
O1 C1 C2 C7 -54.1(2) . . . . ?
C6 C1 C2 C7 -175.72(17) . . . . ?
C1 C2 C3 C4 -56.1(2) . . . . ?
C7 C2 C3 C4 177.35(17) . . . . ?
C2 C3 C4 C5 57.6(2) . . . . ?
C3 C4 C5 C6 -55.6(2) . . . . ?
C3 C4 C5 C10 -179.2(2) . . . . ?
O1 C1 C6 C5 -179.01(15) . . . . ?
C2 C1 C6 C5 -59.0(2) . . . . ?
C10 C5 C6 C1 179.88(18) . . . . ?
C4 C5 C6 C1 55.9(2) . . . . ?
C6 C1 O1 P1 -76.83(18) . . . . ?
C2 C1 O1 P1 160.10(12) . . . . ?
C1 O1 P1 O2 99.95(16) . . . . ?
C1 O1 P1 F1 -150.54(15) . . . . ?
C1 O1 P1 S1 -35.58(16) . . . . ?
C1 C2 C7 C9 -60.5(2) . . . . ?
C3 C2 C7 C9 63.0(2) . . . . ?
C1 C2 C7 C8 173.36(19) . . . . ?
C3 C2 C7 C8 -63.1(2) . . . . ?
C15 N1 C11 C12 -1.2(3) . . . . ?
N1 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 2.6(3) . . . . ?
C11 C12 C13 C16 -175.6(2) . . . . ?
C12 C13 C14 C15 -2.5(3) . . . . ?
C16 C13 C14 C15 175.6(2) . . . . ?
C11 N1 C15 C14 1.2(3) . . . . ?
C13 C14 C15 N1 0.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.129
_database_code_depnum_ccdc_archive 'CCDC 1012135'
