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# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  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.
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#  fide research purposes only. It may contain copyright material
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data_121023a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H19 F3 N2 O4 S'
_chemical_formula_weight         332.34

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'
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   P2(1)2(1)2(1)

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

_cell_length_a                   7.76(3)
_cell_length_b                   9.31(3)
_cell_length_c                   21.48(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1552(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2609
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      23.67

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9506
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7836
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2748
_reflns_number_gt                2417
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0466P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0111(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_number_reflns         2748
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 -0.1653(3) 0.0771(2) 0.84339(12) 0.0512(7) Uani 1 1 d . . .
H1A H -0.2666 0.0515 0.8674 0.061 Uiso 1 1 calc R . .
H1B H -0.1956 0.0795 0.7996 0.061 Uiso 1 1 calc R . .
C2 C -0.0210(4) -0.0268(2) 0.85510(12) 0.0509(6) Uani 1 1 d . . .
H2A H -0.0325 -0.1118 0.8293 0.061 Uiso 1 1 calc R . .
H2B H -0.0170 -0.0553 0.8985 0.061 Uiso 1 1 calc R . .
C3 C 0.1367(3) 0.0589(2) 0.83735(12) 0.0481(6) Uani 1 1 d . . .
H3A H 0.1499 0.0637 0.7925 0.058 Uiso 1 1 calc R . .
H3B H 0.2401 0.0177 0.8554 0.058 Uiso 1 1 calc R . .
C4 C 0.0992(3) 0.2072(2) 0.86476(10) 0.0347(5) Uani 1 1 d . . .
H4 H 0.1405 0.2106 0.9079 0.042 Uiso 1 1 calc R . .
C5 C 0.1788(3) 0.3289(2) 0.82835(9) 0.0358(5) Uani 1 1 d . . .
C6 C 0.5076(4) 0.6019(2) 0.85624(10) 0.0450(6) Uani 1 1 d . . .
C7 C 0.5451(4) 0.5428(3) 0.92020(11) 0.0576(7) Uani 1 1 d . . .
H7A H 0.6357 0.4729 0.9175 0.086 Uiso 1 1 calc R . .
H7B H 0.4432 0.4984 0.9366 0.086 Uiso 1 1 calc R . .
H7C H 0.5803 0.6196 0.9472 0.086 Uiso 1 1 calc R . .
C8 C 0.6573(4) 0.6896(3) 0.83156(15) 0.0767(10) Uani 1 1 d . . .
H8A H 0.6656 0.7778 0.8545 0.115 Uiso 1 1 calc R . .
H8B H 0.6388 0.7106 0.7883 0.115 Uiso 1 1 calc R . .
H8C H 0.7622 0.6361 0.8362 0.115 Uiso 1 1 calc R . .
C9 C 0.3394(4) 0.6858(3) 0.85407(12) 0.0589(7) Uani 1 1 d . . .
H9A H 0.3441 0.7635 0.8834 0.088 Uiso 1 1 calc R . .
H9B H 0.2454 0.6232 0.8645 0.088 Uiso 1 1 calc R . .
H9C H 0.3225 0.7236 0.8129 0.088 Uiso 1 1 calc R . .
C10 C -0.0481(3) 0.3604(3) 1.02363(9) 0.0418(6) Uani 1 1 d . . .
C11 C 0.0112(4) 0.5005(3) 0.99495(11) 0.0511(6) Uani 1 1 d . . .
F1 F 0.0189(3) 0.49676(16) 0.93323(7) 0.0846(6) Uani 1 1 d . . .
F2 F -0.0978(3) 0.60697(18) 1.00815(9) 0.0867(6) Uani 1 1 d . . .
F3 F 0.1636(2) 0.5454(2) 1.01479(9) 0.0877(6) Uani 1 1 d . . .
N1 N -0.0936(2) 0.2190(2) 0.86419(8) 0.0358(5) Uani 1 1 d . . .
H1C H -0.1268 0.2890 0.8379 0.043 Uiso 1 1 calc R . .
H1D H -0.1325 0.2406 0.9025 0.043 Uiso 1 1 calc R . .
N2 N 0.3487(2) 0.34716(19) 0.84062(8) 0.0383(4) Uani 1 1 d . . .
H2 H 0.3921 0.3003 0.8713 0.046 Uiso 1 1 calc R . .
O1 O 0.0962(2) 0.39840(18) 0.79114(7) 0.0506(5) Uani 1 1 d . . .
O2 O 0.6473(2) 0.37798(18) 0.79712(7) 0.0508(4) Uani 1 1 d . . .
O3 O -0.0138(3) 0.34889(19) 1.07938(7) 0.0585(5) Uani 1 1 d . . .
O4 O -0.1284(3) 0.27701(18) 0.99025(7) 0.0583(5) Uani 1 1 d . . .
S1 S 0.48092(7) 0.45591(6) 0.79964(2) 0.03841(17) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0400(15) 0.0504(15) 0.0631(16) -0.0163(12) 0.0059(11) -0.0158(13)
C2 0.0538(16) 0.0365(12) 0.0624(15) -0.0078(11) 0.0043(13) -0.0094(15)
C3 0.0413(14) 0.0341(12) 0.0688(16) -0.0037(12) 0.0053(12) 0.0005(13)
C4 0.0303(12) 0.0374(13) 0.0363(12) -0.0004(10) -0.0030(9) -0.0033(11)
C5 0.0404(14) 0.0336(11) 0.0333(10) -0.0049(9) -0.0022(9) -0.0004(11)
C6 0.0461(15) 0.0384(11) 0.0506(12) 0.0003(10) 0.0000(12) -0.0084(13)
C7 0.067(2) 0.0569(15) 0.0487(14) -0.0092(12) -0.0112(12) -0.0089(16)
C8 0.080(2) 0.0635(18) 0.087(2) -0.0020(16) 0.0124(17) -0.0350(19)
C9 0.072(2) 0.0443(14) 0.0606(17) 0.0013(13) 0.0043(14) 0.0091(15)
C10 0.0421(15) 0.0500(14) 0.0333(11) -0.0008(10) 0.0070(10) -0.0060(12)
C11 0.0617(18) 0.0512(14) 0.0405(12) -0.0045(10) 0.0063(13) -0.0047(16)
F1 0.1412(18) 0.0692(10) 0.0434(8) 0.0077(7) 0.0191(10) -0.0249(12)
F2 0.1156(17) 0.0563(10) 0.0881(12) -0.0097(9) 0.0031(11) 0.0149(11)
F3 0.0781(13) 0.0887(13) 0.0961(12) 0.0224(11) -0.0105(10) -0.0415(12)
N1 0.0355(11) 0.0380(11) 0.0340(10) -0.0025(8) 0.0021(7) -0.0007(9)
N2 0.0345(11) 0.0408(10) 0.0396(10) 0.0085(8) -0.0061(8) -0.0064(9)
O1 0.0412(10) 0.0597(10) 0.0510(9) 0.0189(8) -0.0093(8) -0.0010(9)
O2 0.0374(9) 0.0581(10) 0.0570(10) -0.0037(9) 0.0047(8) 0.0050(8)
O3 0.0666(12) 0.0719(11) 0.0370(9) 0.0055(8) 0.0005(8) -0.0228(12)
O4 0.0698(13) 0.0617(12) 0.0434(9) -0.0026(9) -0.0012(8) -0.0222(11)
S1 0.0368(3) 0.0419(3) 0.0366(3) 0.0034(2) -0.0003(2) -0.0026(3)

_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 C2 1.501(5) . ?
C1 N1 1.503(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.510(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.529(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.500(6) . ?
C4 C5 1.509(5) . ?
C4 H4 0.9800 . ?
C5 O1 1.212(4) . ?
C5 N2 1.355(6) . ?
C6 C7 1.508(6) . ?
C6 C8 1.516(5) . ?
C6 C9 1.523(6) . ?
C6 S1 1.835(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
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 O4 1.227(4) . ?
C10 O3 1.231(5) . ?
C10 C11 1.514(6) . ?
C11 F3 1.325(5) . ?
C11 F1 1.328(6) . ?
C11 F2 1.333(5) . ?
N1 H1C 0.9000 . ?
N1 H1D 0.9000 . ?
N2 S1 1.689(4) . ?
N2 H2 0.8600 . ?
O2 S1 1.482(5) . ?

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
C2 C1 N1 103.9(3) . . ?
C2 C1 H1A 111.0 . . ?
N1 C1 H1A 111.0 . . ?
C2 C1 H1B 111.0 . . ?
N1 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C1 C2 C3 102.8(3) . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C2 C3 C4 103.1(3) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C5 110.4(2) . . ?
N1 C4 C3 104.7(2) . . ?
C5 C4 C3 113.6(3) . . ?
N1 C4 H4 109.3 . . ?
C5 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
O1 C5 N2 125.1(2) . . ?
O1 C5 C4 121.8(3) . . ?
N2 C5 C4 113.1(2) . . ?
C7 C6 C8 111.6(3) . . ?
C7 C6 C9 112.3(2) . . ?
C8 C6 C9 111.7(3) . . ?
C7 C6 S1 110.8(3) . . ?
C8 C6 S1 104.7(3) . . ?
C9 C6 S1 105.2(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 O3 128.6(3) . . ?
O4 C10 C11 117.5(3) . . ?
O3 C10 C11 113.9(2) . . ?
F3 C11 F1 106.8(2) . . ?
F3 C11 F2 105.3(3) . . ?
F1 C11 F2 105.1(2) . . ?
F3 C11 C10 114.3(2) . . ?
F1 C11 C10 113.4(2) . . ?
F2 C11 C10 111.2(3) . . ?
C4 N1 C1 107.9(2) . . ?
C4 N1 H1C 110.1 . . ?
C1 N1 H1C 110.1 . . ?
C4 N1 H1D 110.1 . . ?
C1 N1 H1D 110.1 . . ?
H1C N1 H1D 108.4 . . ?
C5 N2 S1 124.4(2) . . ?
C5 N2 H2 117.8 . . ?
S1 N2 H2 117.8 . . ?
O2 S1 N2 104.8(3) . . ?
O2 S1 C6 106.75(18) . . ?
N2 S1 C6 99.6(3) . . ?

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
N1 H1D O4 0.90 1.91 2.774(10) 159.1 .
N1 H1C O2 0.90 2.13 2.883(7) 140.9 1_455
N1 H1C O1 0.90 2.25 2.724(6) 112.9 .
N2 H2 O3 0.86 1.89 2.725(7) 162.3 4_557

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 940363'
