# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 F3 N2 O3 S'
_chemical_formula_weight         386.39

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.555(3)
_cell_length_b                   8.9872(18)
_cell_length_c                   15.716(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.99(3)
_cell_angle_gamma                90.00
_cell_volume                     1762.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.1500
_cell_measurement_reflns_used    4983
_cell_measurement_theta_min      1.63
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .633
_exptl_crystal_size_mid          .441
_exptl_crystal_size_min          .357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  .884
_exptl_absorpt_correction_T_max  .920

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173.1500
_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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            12272
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4033
_reflns_number_gt                3758
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_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)+(0.0803P)²+0.8634P] 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_number_reflns         4033
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.0659
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1576
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_restrained_S_all      1.171
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.13560(4) 0.61939(7) 0.21329(4) 0.03474(19) Uani 1 1 d . . .
O1 O 0.10145(14) 0.5422(2) 0.27714(12) 0.0469(5) Uani 1 1 d . . .
N1 N 0.04420(14) 1.2114(2) 0.11408(12) 0.0298(4) Uani 1 1 d . . .
N2 N 0.18180(14) 1.1608(2) 0.24153(11) 0.0290(4) Uani 1 1 d . . .
F1 F 0.32927(13) 0.5310(2) 0.31691(14) 0.0655(5) Uani 1 1 d . . .
C5 C 0.20967(17) 1.1171(2) 0.16853(14) 0.0283(4) Uani 1 1 d . . .
F2 F 0.32463(14) 0.7158(2) 0.22938(15) 0.0673(5) Uani 1 1 d . . .
C7 C 0.24386(17) 1.1412(2) 0.33823(14) 0.0290(4) Uani 1 1 d . . .
C8 C 0.12183(18) 1.1193(2) 0.00072(15) 0.0335(5) Uani 1 1 d . . .
H8A H 0.0635 1.1418 -0.0534 0.040 Uiso 1 1 calc R . .
C9 C 0.08239(17) 1.2166(2) 0.20508(15) 0.0310(4) Uani 1 1 d . . .
H9A H 0.0453 1.2538 0.2393 0.037 Uiso 1 1 calc R . .
O3 O 0.09057(15) 0.7655(2) 0.18848(14) 0.0527(5) Uani 1 1 d . . .
C11 C 0.12209(16) 1.1502(2) 0.08737(14) 0.0280(4) Uani 1 1 d . . .
O2 O 0.13829(17) 0.5296(2) 0.13860(13) 0.0534(5) Uani 1 1 d . . .
C13 C 0.40853(18) 1.1664(3) 0.46975(15) 0.0369(5) Uani 1 1 d . . .
H13A H 0.4801 1.1950 0.4952 0.044 Uiso 1 1 calc R . .
F3 F 0.29104(15) 0.7461(2) 0.35113(14) 0.0752(6) Uani 1 1 d . . .
C15 C 0.19658(17) 1.0768(3) 0.39284(15) 0.0329(5) Uani 1 1 d . . .
H15A H 0.1256 1.0456 0.3667 0.039 Uiso 1 1 calc R . .
C16 C 0.34957(17) 1.1872(3) 0.37628(15) 0.0340(5) Uani 1 1 d . . .
H16A H 0.3807 1.2317 0.3394 0.041 Uiso 1 1 calc R . .
C17 C 0.30098(17) 1.0487(2) 0.16679(15) 0.0319(5) Uani 1 1 d . . .
H17A H 0.3589 1.0253 0.2211 0.038 Uiso 1 1 calc R . .
C18 C 0.25548(18) 1.0590(3) 0.48655(15) 0.0352(5) Uani 1 1 d . . .
H18A H 0.2234 1.0169 0.5234 0.042 Uiso 1 1 calc R . .
C19 C 0.36250(18) 1.1035(3) 0.52627(15) 0.0344(5) Uani 1 1 d . . .
C20 C -0.05786(17) 1.2738(3) 0.05179(16) 0.0371(5) Uani 1 1 d . . .
H20A H -0.0973 1.3085 0.0871 0.056 Uiso 1 1 calc R . .
H20B H -0.0986 1.1985 0.0093 0.056 Uiso 1 1 calc R . .
H20C H -0.0449 1.3553 0.0181 0.056 Uiso 1 1 calc R . .
C21 C 0.30216(18) 1.0168(3) 0.08103(16) 0.0355(5) Uani 1 1 d . . .
C22 C 0.2770(2) 0.6552(3) 0.28099(18) 0.0435(6) Uani 1 1 d . . .
C23 C 0.21355(19) 1.0530(3) -0.00040(15) 0.0358(5) Uani 1 1 d . . .
H23A H 0.2168 1.0314 -0.0571 0.043 Uiso 1 1 calc R . .
C24 C 0.4260(2) 1.0849(3) 0.62876(17) 0.0486(6) Uani 1 1 d . . .
H24A H 0.4977 1.1209 0.6443 0.073 Uiso 1 1 calc R . .
H24B H 0.4283 0.9815 0.6448 0.073 Uiso 1 1 calc R . .
H24C H 0.3925 1.1405 0.6623 0.073 Uiso 1 1 calc R . .
C25 C 0.3976(2) 0.9388(4) 0.0746(2) 0.0531(7) Uani 1 1 d . . .
H25A H 0.4507 0.9221 0.1357 0.080 Uiso 1 1 calc R . .
H25B H 0.4274 0.9996 0.0404 0.080 Uiso 1 1 calc R . .
H25C H 0.3753 0.8451 0.0437 0.080 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
S1 O2 1.4364(19) . ?
S1 O3 1.436(2) . ?
S1 O1 1.4369(17) . ?
S1 C22 1.821(3) . ?
N1 C9 1.318(3) . ?
N1 C11 1.393(3) . ?
N1 C20 1.459(3) . ?
N2 C9 1.339(3) . ?
N2 C5 1.397(3) . ?
N2 C7 1.432(3) . ?
F1 C22 1.325(3) . ?
C5 C17 1.392(3) . ?
C5 C11 1.394(3) . ?
F2 C22 1.335(3) . ?
C7 C15 1.383(3) . ?
C7 C16 1.383(3) . ?
C8 C23 1.385(3) . ?
C8 C11 1.388(3) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C13 C16 1.384(3) . ?
C13 C19 1.390(3) . ?
C13 H13A 0.9300 . ?
F3 C22 1.325(3) . ?
C15 C18 1.383(3) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C21 1.384(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.395(3) . ?
C18 H18A 0.9300 . ?
C19 C24 1.510(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C23 1.409(3) . ?
C21 C25 1.509(3) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
O2 S1 O3 115.80(13) . . ?
O2 S1 O1 114.68(12) . . ?
O3 S1 O1 114.34(12) . . ?
O2 S1 C22 102.71(12) . . ?
O3 S1 C22 103.63(12) . . ?
O1 S1 C22 103.28(12) . . ?
C9 N1 C11 108.55(17) . . ?
C9 N1 C20 125.62(18) . . ?
C11 N1 C20 125.54(18) . . ?
C9 N2 C5 107.68(17) . . ?
C9 N2 C7 125.19(18) . . ?
C5 N2 C7 127.00(18) . . ?
C17 C5 C11 121.51(19) . . ?
C17 C5 N2 131.91(19) . . ?
C11 C5 N2 106.54(18) . . ?
C15 C7 C16 120.66(19) . . ?
C15 C7 N2 119.19(19) . . ?
C16 C7 N2 120.15(18) . . ?
C23 C8 C11 116.1(2) . . ?
C23 C8 H8A 121.9 . . ?
C11 C8 H8A 121.9 . . ?
N1 C9 N2 110.76(19) . . ?
N1 C9 H9A 124.6 . . ?
N2 C9 H9A 124.6 . . ?
C8 C11 N1 131.51(19) . . ?
C8 C11 C5 122.00(19) . . ?
N1 C11 C5 106.47(18) . . ?
C16 C13 C19 121.1(2) . . ?
C16 C13 H13A 119.5 . . ?
C19 C13 H13A 119.5 . . ?
C7 C15 C18 119.6(2) . . ?
C7 C15 H15A 120.2 . . ?
C18 C15 H15A 120.2 . . ?
C7 C16 C13 119.3(2) . . ?
C7 C16 H16A 120.3 . . ?
C13 C16 H16A 120.3 . . ?
C21 C17 C5 117.3(2) . . ?
C21 C17 H17A 121.3 . . ?
C5 C17 H17A 121.3 . . ?
C15 C18 C19 120.7(2) . . ?
C15 C18 H18A 119.7 . . ?
C19 C18 H18A 119.7 . . ?
C13 C19 C18 118.6(2) . . ?
C13 C19 C24 121.0(2) . . ?
C18 C19 C24 120.4(2) . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 C23 120.4(2) . . ?
C17 C21 C25 119.8(2) . . ?
C23 C21 C25 119.7(2) . . ?
F3 C22 F1 106.6(2) . . ?
F3 C22 F2 107.9(2) . . ?
F1 C22 F2 107.3(2) . . ?
F3 C22 S1 111.84(18) . . ?
F1 C22 S1 111.48(18) . . ?
F2 C22 S1 111.45(19) . . ?
C8 C23 C21 122.6(2) . . ?
C8 C23 H23A 118.7 . . ?
C21 C23 H23A 118.7 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C9 N2 C5 C17 -177.6(2) . . . . ?
C7 N2 C5 C17 -1.6(4) . . . . ?
C9 N2 C5 C11 0.2(2) . . . . ?
C7 N2 C5 C11 176.20(19) . . . . ?
C9 N2 C7 C15 46.4(3) . . . . ?
C5 N2 C7 C15 -128.9(2) . . . . ?
C9 N2 C7 C16 -133.1(2) . . . . ?
C5 N2 C7 C16 51.5(3) . . . . ?
C11 N1 C9 N2 -0.5(2) . . . . ?
C20 N1 C9 N2 -174.61(19) . . . . ?
C5 N2 C9 N1 0.2(2) . . . . ?
C7 N2 C9 N1 -175.89(19) . . . . ?
C23 C8 C11 N1 -178.1(2) . . . . ?
C23 C8 C11 C5 0.3(3) . . . . ?
C9 N1 C11 C8 179.2(2) . . . . ?
C20 N1 C11 C8 -6.8(4) . . . . ?
C9 N1 C11 C5 0.6(2) . . . . ?
C20 N1 C11 C5 174.71(19) . . . . ?
C17 C5 C11 C8 -1.1(3) . . . . ?
N2 C5 C11 C8 -179.19(19) . . . . ?
C17 C5 C11 N1 177.57(19) . . . . ?
N2 C5 C11 N1 -0.5(2) . . . . ?
C16 C7 C15 C18 0.3(3) . . . . ?
N2 C7 C15 C18 -179.2(2) . . . . ?
C15 C7 C16 C13 0.9(3) . . . . ?
N2 C7 C16 C13 -179.5(2) . . . . ?
C19 C13 C16 C7 -1.6(4) . . . . ?
C11 C5 C17 C21 1.0(3) . . . . ?
N2 C5 C17 C21 178.5(2) . . . . ?
C7 C15 C18 C19 -0.9(4) . . . . ?
C16 C13 C19 C18 1.1(4) . . . . ?
C16 C13 C19 C24 -178.2(2) . . . . ?
C15 C18 C19 C13 0.2(4) . . . . ?
C15 C18 C19 C24 179.5(2) . . . . ?
C5 C17 C21 C23 -0.1(3) . . . . ?
C5 C17 C21 C25 -178.3(2) . . . . ?
O2 S1 C22 F3 175.89(19) . . . . ?
O3 S1 C22 F3 55.0(2) . . . . ?
O1 S1 C22 F3 -64.6(2) . . . . ?
O2 S1 C22 F1 -64.9(2) . . . . ?
O3 S1 C22 F1 174.22(19) . . . . ?
O1 S1 C22 F1 54.7(2) . . . . ?
O2 S1 C22 F2 55.0(2) . . . . ?
O3 S1 C22 F2 -65.9(2) . . . . ?
O1 S1 C22 F2 174.52(18) . . . . ?
C11 C8 C23 C21 0.7(3) . . . . ?
C17 C21 C23 C8 -0.8(4) . . . . ?
C25 C21 C23 C8 177.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.162
_database_code_depnum_ccdc_archive 'CCDC 978439'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 F3 N2 O'
_chemical_formula_weight         306.28

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.805(2)
_cell_length_b                   9.3144(19)
_cell_length_c                   15.513(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.91(3)
_cell_angle_gamma                90.00
_cell_volume                     1403.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.1500
_cell_measurement_reflns_used    4270
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      27.44

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          .509
_exptl_crystal_size_mid          .354
_exptl_crystal_size_min          .106
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.987

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173.1500
_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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            9452
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.44
_reflns_number_total             3196
_reflns_number_gt                2883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_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)+(0.0592P)²+0.9874P] 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_number_reflns         3196
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.0784
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.1652
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.83883(17) 0.72216(17) 0.13828(10) 0.0359(4) Uani 1 1 d . . .
N1 N 0.83256(18) 0.27520(19) -0.03704(11) 0.0289(4) Uani 1 1 d . . .
F1 F 0.33934(18) 0.2034(2) -0.33783(11) 0.0714(6) Uani 1 1 d . . .
C4 C 0.6785(2) 0.2221(3) -0.26554(14) 0.0346(5) Uani 1 1 d . . .
H4A H 0.7008 0.1790 -0.3158 0.042 Uiso 1 1 calc R . .
C5 C 0.8172(2) 0.5159(2) 0.04042(13) 0.0273(4) Uani 1 1 d . . .
H5A H 0.7542 0.5607 -0.0014 0.033 Uiso 1 1 calc R . .
N2 N 0.99059(19) 0.1697(2) 0.06203(12) 0.0341(4) Uani 1 1 d . . .
C7 C 0.7378(2) 0.2837(2) -0.11456(13) 0.0269(4) Uani 1 1 d . . .
F2 F 0.49879(19) 0.2335(3) -0.41513(10) 0.0776(7) Uani 1 1 d . . .
C9 C 0.9601(2) 0.3071(2) 0.09081(13) 0.0279(4) Uani 1 1 d . . .
C10 C 0.5512(2) 0.2864(2) -0.26570(14) 0.0318(5) Uani 1 1 d . . .
C11 C 1.0142(2) 0.3787(2) 0.16697(13) 0.0311(5) Uani 1 1 d . . .
H11A H 1.0796 0.3353 0.2078 0.037 Uiso 1 1 calc R . .
C12 C 0.8622(2) 0.3750(2) 0.03005(13) 0.0263(4) Uani 1 1 d . . .
F3 F 0.3999(2) 0.4152(2) -0.36854(12) 0.0731(6) Uani 1 1 d . . .
C14 C 0.8720(2) 0.5846(2) 0.11672(13) 0.0292(5) Uani 1 1 d . . .
C15 C 0.7723(2) 0.2222(2) -0.19034(14) 0.0324(5) Uani 1 1 d . . .
H15A H 0.8586 0.1809 -0.1904 0.039 Uiso 1 1 calc R . .
C16 C 0.7463(2) 0.8015(2) 0.07633(14) 0.0335(5) Uani 1 1 d . . .
H16A H 0.6602 0.7497 0.0621 0.040 Uiso 1 1 calc R . .
H16B H 0.7865 0.8159 0.0233 0.040 Uiso 1 1 calc R . .
C17 C 0.9677(2) 0.5161(2) 0.17977(13) 0.0303(5) Uani 1 1 d . . .
H17A H 1.0001 0.5643 0.2310 0.036 Uiso 1 1 calc R . .
C18 C 0.5170(2) 0.3506(3) -0.19052(14) 0.0349(5) Uani 1 1 d . . .
H18A H 0.4319 0.3949 -0.1913 0.042 Uiso 1 1 calc R . .
C19 C 0.9130(2) 0.1564(2) -0.01305(15) 0.0344(5) Uani 1 1 d . . .
H19A H 0.9122 0.0743 -0.0472 0.041 Uiso 1 1 calc R . .
C20 C 0.6099(2) 0.3486(2) -0.11454(14) 0.0315(5) Uani 1 1 d . . .
H20A H 0.5869 0.3903 -0.0640 0.038 Uiso 1 1 calc R . .
C21 C 0.7214(3) 0.9438(3) 0.11756(17) 0.0443(6) Uani 1 1 d . . .
H21A H 0.6596 1.0002 0.0777 0.066 Uiso 1 1 calc R . .
H21B H 0.8072 0.9938 0.1313 0.066 Uiso 1 1 calc R . .
H21C H 0.6814 0.9280 0.1699 0.066 Uiso 1 1 calc R . .
C22 C 0.4475(3) 0.2855(3) -0.34582(16) 0.0413(6) Uani 1 1 d . . .


_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
O1 C14 1.374(3) . ?
O1 C16 1.433(3) . ?
N1 C19 1.380(3) . ?
N1 C12 1.396(3) . ?
N1 C7 1.417(3) . ?
F1 C22 1.327(3) . ?
C4 C15 1.382(3) . ?
C4 C10 1.384(3) . ?
C4 H4A 0.9300 . ?
C5 C14 1.387(3) . ?
C5 C12 1.401(3) . ?
C5 H5A 0.9300 . ?
N2 C19 1.306(3) . ?
N2 C9 1.401(3) . ?
C7 C15 1.391(3) . ?
C7 C20 1.392(3) . ?
F2 C22 1.339(3) . ?
C9 C11 1.396(3) . ?
C9 C12 1.400(3) . ?
C10 C18 1.392(3) . ?
C10 C22 1.493(3) . ?
C11 C17 1.382(3) . ?
C11 H11A 0.9300 . ?
F3 C22 1.325(3) . ?
C14 C17 1.411(3) . ?
C15 H15A 0.9300 . ?
C16 C21 1.506(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9300 . ?
C18 C20 1.387(3) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C14 O1 C16 117.82(16) . . ?
C19 N1 C12 106.28(17) . . ?
C19 N1 C7 123.89(18) . . ?
C12 N1 C7 129.81(18) . . ?
C15 C4 C10 119.7(2) . . ?
C15 C4 H4A 120.1 . . ?
C10 C4 H4A 120.1 . . ?
C14 C5 C12 116.03(19) . . ?
C14 C5 H5A 122.0 . . ?
C12 C5 H5A 122.0 . . ?
C19 N2 C9 104.32(18) . . ?
C15 C7 C20 120.2(2) . . ?
C15 C7 N1 119.16(19) . . ?
C20 C7 N1 120.63(19) . . ?
C11 C9 C12 119.9(2) . . ?
C11 C9 N2 129.28(19) . . ?
C12 C9 N2 110.79(18) . . ?
C4 C10 C18 120.4(2) . . ?
C4 C10 C22 120.6(2) . . ?
C18 C10 C22 119.0(2) . . ?
C17 C11 C9 118.01(19) . . ?
C17 C11 H11A 121.0 . . ?
C9 C11 H11A 121.0 . . ?
N1 C12 C9 104.70(18) . . ?
N1 C12 C5 132.29(19) . . ?
C9 C12 C5 122.94(19) . . ?
O1 C14 C5 124.10(19) . . ?
O1 C14 C17 114.22(18) . . ?
C5 C14 C17 121.7(2) . . ?
C4 C15 C7 120.2(2) . . ?
C4 C15 H15A 119.9 . . ?
C7 C15 H15A 119.9 . . ?
O1 C16 C21 107.07(18) . . ?
O1 C16 H16A 110.3 . . ?
C21 C16 H16A 110.3 . . ?
O1 C16 H16B 110.3 . . ?
C21 C16 H16B 110.3 . . ?
H16A C16 H16B 108.6 . . ?
C11 C17 C14 121.36(19) . . ?
C11 C17 H17A 119.3 . . ?
C14 C17 H17A 119.3 . . ?
C20 C18 C10 120.0(2) . . ?
C20 C18 H18A 120.0 . . ?
C10 C18 H18A 120.0 . . ?
N2 C19 N1 113.9(2) . . ?
N2 C19 H19A 123.0 . . ?
N1 C19 H19A 123.0 . . ?
C18 C20 C7 119.5(2) . . ?
C18 C20 H20A 120.3 . . ?
C7 C20 H20A 120.3 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F3 C22 F1 107.0(2) . . ?
F3 C22 F2 105.9(2) . . ?
F1 C22 F2 105.0(2) . . ?
F3 C22 C10 113.0(2) . . ?
F1 C22 C10 112.7(2) . . ?
F2 C22 C10 112.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N1 C7 C15 -38.1(3) . . . . ?
C12 N1 C7 C15 144.1(2) . . . . ?
C19 N1 C7 C20 139.8(2) . . . . ?
C12 N1 C7 C20 -38.1(3) . . . . ?
C19 N2 C9 C11 -179.2(2) . . . . ?
C19 N2 C9 C12 -0.3(2) . . . . ?
C15 C4 C10 C18 -0.2(3) . . . . ?
C15 C4 C10 C22 -179.1(2) . . . . ?
C12 C9 C11 C17 0.3(3) . . . . ?
N2 C9 C11 C17 179.1(2) . . . . ?
C19 N1 C12 C9 -0.2(2) . . . . ?
C7 N1 C12 C9 178.0(2) . . . . ?
C19 N1 C12 C5 176.9(2) . . . . ?
C7 N1 C12 C5 -5.0(4) . . . . ?
C11 C9 C12 N1 179.33(19) . . . . ?
N2 C9 C12 N1 0.3(2) . . . . ?
C11 C9 C12 C5 1.9(3) . . . . ?
N2 C9 C12 C5 -177.15(19) . . . . ?
C14 C5 C12 N1 -178.7(2) . . . . ?
C14 C5 C12 C9 -2.1(3) . . . . ?
C16 O1 C14 C5 -2.8(3) . . . . ?
C16 O1 C14 C17 177.69(19) . . . . ?
C12 C5 C14 O1 -179.35(19) . . . . ?
C12 C5 C14 C17 0.1(3) . . . . ?
C10 C4 C15 C7 1.4(3) . . . . ?
C20 C7 C15 C4 -1.5(3) . . . . ?
N1 C7 C15 C4 176.4(2) . . . . ?
C14 O1 C16 C21 177.0(2) . . . . ?
C9 C11 C17 C14 -2.2(3) . . . . ?
O1 C14 C17 C11 -178.46(19) . . . . ?
C5 C14 C17 C11 2.0(3) . . . . ?
C4 C10 C18 C20 -1.0(3) . . . . ?
C22 C10 C18 C20 177.9(2) . . . . ?
C9 N2 C19 N1 0.1(3) . . . . ?
C12 N1 C19 N2 0.0(3) . . . . ?
C7 N1 C19 N2 -178.24(19) . . . . ?
C10 C18 C20 C7 0.9(3) . . . . ?
C15 C7 C20 C18 0.3(3) . . . . ?
N1 C7 C20 C18 -177.5(2) . . . . ?
C4 C10 C22 F3 -127.3(3) . . . . ?
C18 C10 C22 F3 53.8(3) . . . . ?
C4 C10 C22 F1 111.1(3) . . . . ?
C18 C10 C22 F1 -67.8(3) . . . . ?
C4 C10 C22 F2 -7.4(3) . . . . ?
C18 C10 C22 F2 173.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 978438'
