# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 990785'
_audit_update_record             
;
2014-03-09 deposited with the CCDC.
2015-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 F3 N O4 P S'
_chemical_formula_weight         477.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.5794(6)
_cell_length_b                   12.6291(16)
_cell_length_c                   22.1208(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.615(7)
_cell_angle_gamma                90
_cell_volume                     2395.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2213
_cell_measurement_theta_min      3.4968
_cell_measurement_theta_max      41.5269

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.277
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.78642
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_detector_area_resol_mean 5.2679
_diffrn_measurement_method       '/w scan'
_diffrn_reflns_number            19491
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.998
_diffrn_reflns_theta_max         75.836
_diffrn_reflns_theta_full        70.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4918
_reflns_number_gt                4091
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0762P)²+0.8478P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4918
_refine_ls_number_parameters     290
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.040
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8530(2) 0.62752(17) 0.48134(9) 0.0469(4) Uani 1 1 d . . . . .
H1A H 0.8217 0.5636 0.4590 0.056 Uiso 1 1 calc R U . . .
O1 O 0.90758(19) 0.59949(15) 0.54020(7) 0.0576(4) Uani 1 1 d . . . . .
H11 H 0.879(3) 0.543(3) 0.5458(13) 0.069(9) Uiso 1 1 d . . . . .
P1 P 1.02627(6) 0.68429(4) 0.44845(3) 0.05107(17) Uani 1 1 d . . . . .
O11 O 1.15904(17) 0.61099(14) 0.44653(8) 0.0656(4) Uani 1 1 d . . . . .
O12 O 0.96462(18) 0.72575(16) 0.38561(8) 0.0682(5) Uani 1 1 d . . . . .
C121 C 1.0668(4) 0.7637(4) 0.34107(16) 0.1092(13) Uani 1 1 d D . . . .
H12B H 1.1072 0.7049 0.3181 0.131 Uiso 1 1 calc R U . . .
H12A H 1.1540 0.8008 0.3602 0.131 Uiso 1 1 calc R U . . .
C122 C 0.9753(5) 0.8387(4) 0.2992(2) 0.1294(17) Uani 1 1 d D . . . .
H12E H 0.9288 0.8936 0.3228 0.194 Uiso 1 1 calc R U . . .
H12D H 0.8951 0.8000 0.2777 0.194 Uiso 1 1 calc R U . . .
H12C H 1.0446 0.8698 0.2709 0.194 Uiso 1 1 calc R U . . .
O13 O 1.06093(19) 0.78978(14) 0.48316(9) 0.0675(4) Uani 1 1 d . . . . .
C131 C 1.1499(4) 0.7911(3) 0.53960(17) 0.0976(10) Uani 1 1 d D . . . .
H13B H 1.2584 0.7749 0.5326 0.117 Uiso 1 1 calc R U . . .
H13A H 1.1096 0.7386 0.5671 0.117 Uiso 1 1 calc R U . . .
C132 C 1.1355(10) 0.9017(4) 0.5668(3) 0.220(4) Uani 1 1 d D . . . .
H13E H 1.0291 0.9145 0.5769 0.330 Uiso 1 1 calc R U . . .
H13D H 1.1677 0.9535 0.5379 0.330 Uiso 1 1 calc R U . . .
H13C H 1.2008 0.9066 0.6027 0.330 Uiso 1 1 calc R U . . .
C2 C 0.7142(2) 0.70616(16) 0.48265(9) 0.0453(4) Uani 1 1 d . . . . .
H2A H 0.7555 0.7775 0.4900 0.054 Uiso 1 1 calc R U . . .
S2 S 0.58333(6) 0.67272(5) 0.54351(2) 0.05860(18) Uani 1 1 d . . . . .
C21 C 0.6568(3) 0.7578(2) 0.60177(10) 0.0591(6) Uani 1 1 d . . . . .
C22 C 0.6340(4) 0.8652(3) 0.59948(14) 0.0848(9) Uani 1 1 d . . . . .
H22 H 0.5794 0.8949 0.5667 0.102 Uiso 1 1 calc R U . . .
C23 C 0.6916(5) 0.9301(3) 0.64564(17) 0.1037(12) Uani 1 1 d . . . . .
H23 H 0.6773 1.0030 0.6431 0.124 Uiso 1 1 calc R U . . .
C24 C 0.7687(4) 0.8880(3) 0.69450(15) 0.0892(9) Uani 1 1 d . . . . .
H24 H 0.8070 0.9317 0.7253 0.107 Uiso 1 1 calc R U . . .
C25 C 0.7896(4) 0.7802(3) 0.69795(13) 0.0786(8) Uani 1 1 d . . . . .
H25 H 0.8407 0.7507 0.7316 0.094 Uiso 1 1 calc R U . . .
C26 C 0.7351(3) 0.7156(2) 0.65171(11) 0.0680(6) Uani 1 1 d . . . . .
H26 H 0.7511 0.6429 0.6541 0.082 Uiso 1 1 calc R U . . .
C3 C 0.6247(2) 0.70571(16) 0.42136(9) 0.0470(4) Uani 1 1 d . . . . .
H3 H 0.7032 0.6964 0.3905 0.056 Uiso 1 1 calc R U . . .
C31 C 0.5451(3) 0.8106(2) 0.40769(12) 0.0633(6) Uani 1 1 d . . . . .
F31A F 0.6425(2) 0.89205(13) 0.41333(12) 0.1106(7) Uani 1 1 d . . . . .
F31B F 0.4253(2) 0.83191(16) 0.44149(10) 0.1046(7) Uani 1 1 d . . . . .
F31C F 0.4899(2) 0.81537(14) 0.35085(8) 0.0920(6) Uani 1 1 d . . . . .
N3 N 0.5219(2) 0.61530(15) 0.41613(8) 0.0525(4) Uani 1 1 d . . . . .
H3N H 0.430(4) 0.625(2) 0.4383(14) 0.079(8) Uiso 1 1 d . . . . .
C4 C 0.4870(3) 0.5748(2) 0.35525(11) 0.0636(6) Uani 1 1 d . . . . .
H4B H 0.4383 0.6302 0.3309 0.076 Uiso 1 1 calc R U . . .
H4A H 0.4138 0.5165 0.3576 0.076 Uiso 1 1 calc R U . . .
C41 C 0.6327(3) 0.5375(2) 0.32535(10) 0.0623(6) Uani 1 1 d . . . . .
C42 C 0.6859(4) 0.5850(3) 0.27372(12) 0.0781(8) Uani 1 1 d . . . . .
H42 H 0.6299 0.6407 0.2563 0.094 Uiso 1 1 calc R U . . .
C43 C 0.8212(4) 0.5507(3) 0.24757(14) 0.0961(10) Uani 1 1 d . . . . .
H43 H 0.8556 0.5832 0.2126 0.115 Uiso 1 1 calc R U . . .
C44 C 0.9053(4) 0.4686(3) 0.27324(15) 0.0953(10) Uani 1 1 d . . . . .
H44 H 0.9963 0.4454 0.2556 0.114 Uiso 1 1 calc R U . . .
C45 C 0.8554(4) 0.4213(3) 0.32437(16) 0.0903(9) Uani 1 1 d . . . . .
H45 H 0.9125 0.3663 0.3420 0.108 Uiso 1 1 calc R U . . .
C46 C 0.7190(3) 0.4554(2) 0.35013(13) 0.0748(7) Uani 1 1 d . . . . .
H46 H 0.6849 0.4222 0.3849 0.090 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.416(2) . ?
C1 C2 1.551(3) . ?
C1 P1 1.820(2) . ?
C1 H1A 0.9800 . ?
O1 H11 0.77(3) . ?
P1 O11 1.4694(16) . ?
P1 O13 1.5619(18) . ?
P1 O12 1.5637(17) . ?
O12 C121 1.420(3) . ?
C121 C122 1.5258(19) . ?
C121 H12B 0.9700 . ?
C121 H12A 0.9700 . ?
C122 H12E 0.9600 . ?
C122 H12D 0.9600 . ?
C122 H12C 0.9600 . ?
O13 C131 1.445(4) . ?
C131 C132 1.527(2) . ?
C131 H13B 0.9700 . ?
C131 H13A 0.9700 . ?
C132 H13E 0.9600 . ?
C132 H13D 0.9600 . ?
C132 H13C 0.9600 . ?
C2 C3 1.539(3) . ?
C2 S2 1.827(2) . ?
C2 H2A 0.9800 . ?
S2 C21 1.780(2) . ?
C21 C22 1.371(4) . ?
C21 C26 1.383(3) . ?
C22 C23 1.390(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.360(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.375(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.379(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C3 N3 1.445(3) . ?
C3 C31 1.517(3) . ?
C3 H3 0.9800 . ?
C31 F31B 1.316(3) . ?
C31 F31A 1.328(3) . ?
C31 F31C 1.333(3) . ?
N3 C4 1.464(3) . ?
N3 H3N 0.95(3) . ?
C4 C41 1.507(4) . ?
C4 H4B 0.9700 . ?
C4 H4A 0.9700 . ?
C41 C46 1.378(4) . ?
C41 C42 1.379(4) . ?
C42 C43 1.381(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.377(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.359(5) . ?
C44 H44 0.9300 . ?
C45 C46 1.384(4) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?

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 C2 112.15(17) . . ?
O1 C1 P1 102.32(13) . . ?
C2 C1 P1 113.02(14) . . ?
O1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
P1 C1 H1A 109.7 . . ?
C1 O1 H11 106(2) . . ?
O11 P1 O13 114.49(10) . . ?
O11 P1 O12 115.35(11) . . ?
O13 P1 O12 101.91(11) . . ?
O11 P1 C1 113.95(10) . . ?
O13 P1 C1 106.61(10) . . ?
O12 P1 C1 103.16(9) . . ?
C121 O12 P1 122.00(16) . . ?
O12 C121 C122 108.3(3) . . ?
O12 C121 H12B 110.0 . . ?
C122 C121 H12B 110.0 . . ?
O12 C121 H12A 110.0 . . ?
C122 C121 H12A 110.0 . . ?
H12B C121 H12A 108.4 . . ?
C121 C122 H12E 109.5 . . ?
C121 C122 H12D 109.5 . . ?
H12E C122 H12D 109.5 . . ?
C121 C122 H12C 109.5 . . ?
H12E C122 H12C 109.5 . . ?
H12D C122 H12C 109.5 . . ?
C131 O13 P1 121.55(19) . . ?
O13 C131 C132 107.7(3) . . ?
O13 C131 H13B 110.2 . . ?
C132 C131 H13B 110.2 . . ?
O13 C131 H13A 110.2 . . ?
C132 C131 H13A 110.2 . . ?
H13B C131 H13A 108.5 . . ?
C131 C132 H13E 109.5 . . ?
C131 C132 H13D 109.5 . . ?
H13E C132 H13D 109.5 . . ?
C131 C132 H13C 109.5 . . ?
H13E C132 H13C 109.5 . . ?
H13D C132 H13C 109.5 . . ?
C3 C2 C1 110.21(16) . . ?
C3 C2 S2 110.26(13) . . ?
C1 C2 S2 110.72(14) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
S2 C2 H2A 108.5 . . ?
C21 S2 C2 100.44(10) . . ?
C22 C21 C26 118.5(2) . . ?
C22 C21 S2 121.55(19) . . ?
C26 C21 S2 120.0(2) . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.4(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.7(3) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
N3 C3 C31 113.83(18) . . ?
N3 C3 C2 111.20(16) . . ?
C31 C3 C2 112.51(19) . . ?
N3 C3 H3 106.2 . . ?
C31 C3 H3 106.2 . . ?
C2 C3 H3 106.2 . . ?
F31B C31 F31A 106.7(2) . . ?
F31B C31 F31C 105.3(2) . . ?
F31A C31 F31C 105.1(2) . . ?
F31B C31 C3 114.8(2) . . ?
F31A C31 C3 112.3(2) . . ?
F31C C31 C3 111.9(2) . . ?
C3 N3 C4 117.28(18) . . ?
C3 N3 H3N 111.7(18) . . ?
C4 N3 H3N 111.6(18) . . ?
N3 C4 C41 111.25(18) . . ?
N3 C4 H4B 109.4 . . ?
C41 C4 H4B 109.4 . . ?
N3 C4 H4A 109.4 . . ?
C41 C4 H4A 109.4 . . ?
H4B C4 H4A 108.0 . . ?
C46 C41 C42 118.0(3) . . ?
C46 C41 C4 120.3(2) . . ?
C42 C41 C4 121.7(3) . . ?
C41 C42 C43 120.8(3) . . ?
C41 C42 H42 119.6 . . ?
C43 C42 H42 119.6 . . ?
C44 C43 C42 120.0(3) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C45 C44 C43 120.0(3) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 119.7(3) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C41 C46 C45 121.4(3) . . ?
C41 C46 H46 119.3 . . ?
C45 C46 H46 119.3 . . ?

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 P1 O11 59.44(17) . . . . ?
C2 C1 P1 O11 -179.76(14) . . . . ?
O1 C1 P1 O13 -67.84(15) . . . . ?
C2 C1 P1 O13 52.95(16) . . . . ?
O1 C1 P1 O12 -174.75(14) . . . . ?
C2 C1 P1 O12 -53.96(17) . . . . ?
O11 P1 O12 C121 -46.4(3) . . . . ?
O13 P1 O12 C121 78.3(3) . . . . ?
C1 P1 O12 C121 -171.3(3) . . . . ?
P1 O12 C121 C122 -156.1(3) . . . . ?
O11 P1 O13 C131 -42.1(3) . . . . ?
O12 P1 O13 C131 -167.3(2) . . . . ?
C1 P1 O13 C131 84.9(2) . . . . ?
P1 O13 C131 C132 -169.5(4) . . . . ?
O1 C1 C2 C3 -161.13(17) . . . . ?
P1 C1 C2 C3 83.84(18) . . . . ?
O1 C1 C2 S2 -38.9(2) . . . . ?
P1 C1 C2 S2 -153.90(11) . . . . ?
C3 C2 S2 C21 -142.81(15) . . . . ?
C1 C2 S2 C21 94.96(16) . . . . ?
C2 S2 C21 C22 71.9(2) . . . . ?
C2 S2 C21 C26 -110.1(2) . . . . ?
C26 C21 C22 C23 1.6(5) . . . . ?
S2 C21 C22 C23 179.6(3) . . . . ?
C21 C22 C23 C24 -1.4(6) . . . . ?
C22 C23 C24 C25 0.1(6) . . . . ?
C23 C24 C25 C26 1.1(5) . . . . ?
C24 C25 C26 C21 -0.9(5) . . . . ?
C22 C21 C26 C25 -0.4(4) . . . . ?
S2 C21 C26 C25 -178.5(2) . . . . ?
C1 C2 C3 N3 79.1(2) . . . . ?
S2 C2 C3 N3 -43.4(2) . . . . ?
C1 C2 C3 C31 -151.86(18) . . . . ?
S2 C2 C3 C31 85.61(19) . . . . ?
N3 C3 C31 F31B 57.4(3) . . . . ?
C2 C3 C31 F31B -70.3(3) . . . . ?
N3 C3 C31 F31A 179.5(2) . . . . ?
C2 C3 C31 F31A 51.9(3) . . . . ?
N3 C3 C31 F31C -62.6(3) . . . . ?
C2 C3 C31 F31C 169.76(19) . . . . ?
C31 C3 N3 C4 79.9(3) . . . . ?
C2 C3 N3 C4 -151.77(19) . . . . ?
C3 N3 C4 C41 61.5(3) . . . . ?
N3 C4 C41 C46 61.9(3) . . . . ?
N3 C4 C41 C42 -116.6(3) . . . . ?
C46 C41 C42 C43 0.3(4) . . . . ?
C4 C41 C42 C43 178.9(3) . . . . ?
C41 C42 C43 C44 -0.3(5) . . . . ?
C42 C43 C44 C45 -0.1(6) . . . . ?
C43 C44 C45 C46 0.6(6) . . . . ?
C42 C41 C46 C45 0.2(4) . . . . ?
C4 C41 C46 C45 -178.4(3) . . . . ?
C44 C45 C46 C41 -0.7(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H11 O11 0.77(3) 1.98(3) 2.736(3) 169(3) 3_766
C131 H13A O1 0.97 2.53 3.191(4) 125.6 .
C131 H13B F31B 0.97 2.61 3.294(5) 128.1 1_655
C2 H2A O13 0.98 2.63 3.156(2) 113.6 .
C3 H3 O12 0.98 2.28 3.054(2) 135.2 .
N3 H3N O11 0.95(3) 2.34(3) 3.204(2) 151(2) 1_455
C4 H4B F31C 0.97 2.42 3.040(3) 121.5 .

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 990788'
_audit_update_record             
;
2014-03-09 deposited with the CCDC.
2015-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H21 F3 N O4 P'
_chemical_formula_sum            'C15 H21 F3 N O4 P'
_chemical_formula_weight         367.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.654(4)
_cell_length_b                   5.0589(13)
_cell_length_c                   21.395(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.15(2)
_cell_angle_gamma                90
_cell_volume                     1797.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    867
_cell_measurement_theta_min      4.2690
_cell_measurement_theta_max      22.4190

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.55442
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       '/w scan'
_d_diffrn_reflns_number          10939
_diffrn_reflns_av_unetI/netI     0.1808
_diffrn_reflns_av_R_equivalents  0.1354
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.997
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3136
_reflns_number_gt                1151
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0870P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3136
_refine_ls_number_parameters     220
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2337
_refine_ls_R_factor_gt           0.0810
_refine_ls_wR_factor_ref         0.2214
_refine_ls_wR_factor_gt          0.1727
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.883
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7158(3) -0.0308(11) 0.2257(3) 0.0476(15) Uani 1 1 d . . . . .
H1A H 0.7395 0.1047 0.1999 0.057 Uiso 1 1 calc R U . . .
O1 O 0.6665(2) 0.0881(8) 0.26973(19) 0.0636(13) Uani 1 1 d . . . . .
H H 0.6450 0.2209 0.2542 0.095 Uiso 1 1 calc R U . . .
P1 P 0.65004(10) -0.2438(3) 0.17766(8) 0.0574(6) Uani 1 1 d . . . . .
O11 O 0.6192(2) -0.4693(8) 0.2113(2) 0.0697(13) Uani 1 1 d . . . . .
O12 O 0.5825(2) -0.0631(7) 0.14609(19) 0.0593(12) Uani 1 1 d . . . . .
C121 C 0.5067(4) -0.0353(14) 0.1741(3) 0.086(2) Uani 1 1 d D . . . .
H12B H 0.5136 0.0760 0.2110 0.104 Uiso 1 1 calc R U . . .
H12A H 0.4879 -0.2071 0.1868 0.104 Uiso 1 1 calc R U . . .
C122 C 0.4450(5) 0.089(3) 0.1262(4) 0.177(5) Uani 1 1 d D . . . .
H12E H 0.4340 -0.0308 0.0919 0.265 Uiso 1 1 calc R U . . .
H12D H 0.4662 0.2513 0.1109 0.265 Uiso 1 1 calc R U . . .
H12C H 0.3961 0.1249 0.1459 0.265 Uiso 1 1 calc R U . . .
O13 O 0.7036(2) -0.3086(8) 0.1229(2) 0.0698(13) Uani 1 1 d . . . . .
C131 C 0.6865(5) -0.5213(15) 0.0795(3) 0.099(3) Uani 1 1 d D . . . .
H13B H 0.6636 -0.6682 0.1013 0.119 Uiso 1 1 calc R U . . .
H13A H 0.7364 -0.5812 0.0634 0.119 Uiso 1 1 calc R U . . .
C132 C 0.6277(6) -0.4374(19) 0.0245(4) 0.142(4) Uani 1 1 d D . . . .
H13E H 0.6443 -0.2705 0.0084 0.212 Uiso 1 1 calc R U . . .
H13D H 0.5746 -0.4210 0.0386 0.212 Uiso 1 1 calc R U . . .
H13C H 0.6275 -0.5683 -0.0080 0.212 Uiso 1 1 calc R U . . .
C2 C 0.7816(3) -0.1857(11) 0.2630(3) 0.0516(16) Uani 1 1 d . . . . .
H2 H 0.7615 -0.3126 0.2928 0.062 Uiso 1 1 calc R U . . .
C3 C 0.8603(4) -0.2521(12) 0.2414(3) 0.0547(16) Uani 1 1 d . . . . .
H3 H 0.8833 -0.4150 0.2599 0.066 Uiso 1 1 calc R U . . .
C31 C 0.8948(4) -0.1762(16) 0.1833(4) 0.074(2) Uani 1 1 d . . . . .
F31A F 0.8859(3) -0.3616(9) 0.1393(2) 0.1024(15) Uani 1 1 d . . . . .
F31B F 0.8639(2) 0.0451(8) 0.15668(19) 0.0933(13) Uani 1 1 d . . . . .
F31C F 0.9740(3) -0.1331(9) 0.1918(2) 0.1100(16) Uani 1 1 d . . . . .
N3 N 0.8528(3) -0.0396(9) 0.2869(2) 0.0544(14) Uani 1 1 d . . . . .
C4 C 0.8852(4) -0.1074(13) 0.3513(3) 0.0690(19) Uani 1 1 d . . . . .
H4B H 0.9434 -0.1211 0.3521 0.083 Uiso 1 1 calc R U . . .
H4A H 0.8644 -0.2784 0.3628 0.083 Uiso 1 1 calc R U . . .
C41 C 0.8632(4) 0.0954(12) 0.3987(3) 0.0590(17) Uani 1 1 d . . . . .
C42 C 0.7890(4) 0.2105(15) 0.3966(3) 0.076(2) Uani 1 1 d . . . . .
H42 H 0.7508 0.1691 0.3642 0.091 Uiso 1 1 calc R U . . .
C43 C 0.7704(5) 0.3870(17) 0.4420(4) 0.093(2) Uani 1 1 d . . . . .
H43 H 0.7199 0.4660 0.4400 0.112 Uiso 1 1 calc R U . . .
C44 C 0.8263(5) 0.4483(15) 0.4909(3) 0.082(2) Uani 1 1 d . . . . .
H44 H 0.8137 0.5678 0.5217 0.099 Uiso 1 1 calc R U . . .
C45 C 0.8983(5) 0.3334(19) 0.4930(4) 0.101(3) Uani 1 1 d . . . . .
H45 H 0.9354 0.3689 0.5265 0.121 Uiso 1 1 calc R U . . .
C46 C 0.9193(5) 0.1619(15) 0.4463(4) 0.089(2) Uani 1 1 d . . . . .
H46 H 0.9711 0.0923 0.4472 0.106 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.427(6) . ?
C1 C2 1.525(7) . ?
C1 P1 1.804(5) . ?
C1 H1A 0.9800 . ?
O1 H 0.8200 . ?
P1 O11 1.462(4) . ?
P1 O13 1.558(4) . ?
P1 O12 1.564(4) . ?
O12 C121 1.443(7) . ?
C121 C122 1.534(2) . ?
C121 H12B 0.9700 . ?
C121 H12A 0.9700 . ?
C122 H12E 0.9600 . ?
C122 H12D 0.9600 . ?
C122 H12C 0.9600 . ?
O13 C131 1.436(7) . ?
C131 C132 1.536(2) . ?
C131 H13B 0.9700 . ?
C131 H13A 0.9700 . ?
C132 H13E 0.9600 . ?
C132 H13D 0.9600 . ?
C132 H13C 0.9600 . ?
C2 N3 1.459(7) . ?
C2 C3 1.461(8) . ?
C2 H2 0.9800 . ?
C3 C31 1.458(9) . ?
C3 N3 1.461(7) . ?
C3 H3 0.9800 . ?
C31 F31A 1.331(7) . ?
C31 F31C 1.335(7) . ?
C31 F31B 1.342(8) . ?
N3 C4 1.484(7) . ?
C4 C41 1.506(8) . ?
C4 H4B 0.9700 . ?
C4 H4A 0.9700 . ?
C41 C42 1.364(8) . ?
C41 C46 1.372(8) . ?
C42 C43 1.372(9) . ?
C42 H42 0.9300 . ?
C43 C44 1.383(9) . ?
C43 H43 0.9300 . ?
C44 C45 1.331(9) . ?
C44 H44 0.9300 . ?
C45 C46 1.387(10) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?

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 C2 107.3(5) . . ?
O1 C1 P1 105.9(4) . . ?
C2 C1 P1 112.0(4) . . ?
O1 C1 H1A 110.5 . . ?
C2 C1 H1A 110.5 . . ?
P1 C1 H1A 110.5 . . ?
C1 O1 H 109.5 . . ?
O11 P1 O13 116.5(3) . . ?
O11 P1 O12 113.7(2) . . ?
O13 P1 O12 103.4(2) . . ?
O11 P1 C1 114.0(3) . . ?
O13 P1 C1 101.4(3) . . ?
O12 P1 C1 106.5(2) . . ?
C121 O12 P1 120.1(4) . . ?
O12 C121 C122 109.1(6) . . ?
O12 C121 H12B 109.9 . . ?
C122 C121 H12B 109.9 . . ?
O12 C121 H12A 109.9 . . ?
C122 C121 H12A 109.9 . . ?
H12B C121 H12A 108.3 . . ?
C121 C122 H12E 109.5 . . ?
C121 C122 H12D 109.5 . . ?
H12E C122 H12D 109.5 . . ?
C121 C122 H12C 109.5 . . ?
H12E C122 H12C 109.5 . . ?
H12D C122 H12C 109.5 . . ?
C131 O13 P1 123.2(4) . . ?
O13 C131 C132 112.0(6) . . ?
O13 C131 H13B 109.2 . . ?
C132 C131 H13B 109.2 . . ?
O13 C131 H13A 109.2 . . ?
C132 C131 H13A 109.2 . . ?
H13B C131 H13A 107.9 . . ?
C131 C132 H13E 109.5 . . ?
C131 C132 H13D 109.5 . . ?
H13E C132 H13D 109.5 . . ?
C131 C132 H13C 109.5 . . ?
H13E C132 H13C 109.5 . . ?
H13D C132 H13C 109.5 . . ?
N3 C2 C3 60.1(4) . . ?
N3 C2 C1 117.3(5) . . ?
C3 C2 C1 125.5(5) . . ?
N3 C2 H2 114.3 . . ?
C3 C2 H2 114.3 . . ?
C1 C2 H2 114.3 . . ?
C31 C3 C2 128.8(6) . . ?
C31 C3 N3 115.6(6) . . ?
C2 C3 N3 59.9(4) . . ?
C31 C3 H3 113.5 . . ?
C2 C3 H3 113.5 . . ?
N3 C3 H3 113.5 . . ?
F31A C31 F31C 105.7(6) . . ?
F31A C31 F31B 105.5(6) . . ?
F31C C31 F31B 105.4(6) . . ?
F31A C31 C3 112.8(6) . . ?
F31C C31 C3 112.0(6) . . ?
F31B C31 C3 114.8(6) . . ?
C2 N3 C3 60.0(4) . . ?
C2 N3 C4 116.1(5) . . ?
C3 N3 C4 113.9(5) . . ?
N3 C4 C41 112.2(5) . . ?
N3 C4 H4B 109.2 . . ?
C41 C4 H4B 109.2 . . ?
N3 C4 H4A 109.2 . . ?
C41 C4 H4A 109.2 . . ?
H4B C4 H4A 107.9 . . ?
C42 C41 C46 119.1(7) . . ?
C42 C41 C4 122.2(6) . . ?
C46 C41 C4 118.7(7) . . ?
C41 C42 C43 120.3(7) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C42 C43 C44 120.5(7) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 H43 119.7 . . ?
C45 C44 C43 118.9(8) . . ?
C45 C44 H44 120.6 . . ?
C43 C44 H44 120.6 . . ?
C44 C45 C46 121.5(7) . . ?
C44 C45 H45 119.3 . . ?
C46 C45 H45 119.3 . . ?
C41 C46 C45 119.6(7) . . ?
C41 C46 H46 120.2 . . ?
C45 C46 H46 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A F31B 0.98 2.35 2.990(7) 122.3 .
O1 H O11 0.82 1.85 2.655(5) 166.7 1_565
C131 H13B O12 0.97 2.63 3.592(9) 170.7 1_545

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-4

