# 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_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 Cl F N O3'
_chemical_formula_weight         331.72

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'
Cl Cl 0.1484 0.1585 '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                   6.6455(2)
_cell_length_b                   14.0680(5)
_cell_length_c                   15.4102(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1440.68(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8974
_exptl_absorpt_correction_T_max  0.9387
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16806
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2522
_reflns_number_gt                2143
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0286P)²+0.2864P] 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   -0.06(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2522
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0712
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Cl1 Cl 0.96337(12) 0.67555(6) 0.51204(4) 0.0762(2) Uani 1 1 d . . .
O1 O 0.9206(2) 0.77322(11) 0.98904(9) 0.0483(4) Uani 1 1 d . . .
O2 O 1.2336(2) 0.74845(11) 0.85631(9) 0.0458(4) Uani 1 1 d . . .
H2B H 1.2557 0.7502 0.9086 0.069 Uiso 1 1 calc R . .
C17 C 0.8626(3) 0.94396(15) 0.80205(14) 0.0393(5) Uani 1 1 d . . .
F1 F 1.1197(2) 0.93296(10) 0.91082(8) 0.0551(4) Uani 1 1 d . . .
N1 N 0.7234(3) 0.73175(13) 0.87306(11) 0.0418(5) Uani 1 1 d . . .
H1A H 0.6129 0.7203 0.9002 0.050 Uiso 1 1 calc R . .
C1 C 0.7501(3) 0.71794(14) 0.78356(13) 0.0374(5) Uani 1 1 d . . .
C2 C 0.6174(4) 0.68068(16) 0.72395(14) 0.0466(6) Uani 1 1 d . . .
H2A H 0.4869 0.6642 0.7398 0.056 Uiso 1 1 calc R . .
C3 C 0.6844(4) 0.66849(17) 0.63971(15) 0.0516(6) Uani 1 1 d . . .
H3A H 0.5982 0.6437 0.5979 0.062 Uiso 1 1 calc R . .
C4 C 0.8787(4) 0.69295(16) 0.61751(14) 0.0466(6) Uani 1 1 d . . .
C5 C 1.0112(3) 0.73247(14) 0.67702(13) 0.0404(5) Uani 1 1 d . . .
H5A H 1.1411 0.7497 0.6610 0.048 Uiso 1 1 calc R . .
C6 C 0.9437(3) 0.74535(14) 0.76054(13) 0.0352(5) Uani 1 1 d . . .
C7 C 1.0440(3) 0.78845(14) 0.83918(13) 0.0351(5) Uani 1 1 d . . .
C8 C 0.8909(3) 0.76496(15) 0.91127(14) 0.0373(5) Uani 1 1 d . . .
C9 C 0.8853(3) 0.97314(14) 0.71154(13) 0.0372(5) Uani 1 1 d . . .
C10 C 0.7380(4) 1.00276(16) 0.65416(14) 0.0478(6) Uani 1 1 d . . .
H10A H 0.6047 1.0082 0.6719 0.057 Uiso 1 1 calc R . .
C11 C 0.7930(4) 1.02396(17) 0.57051(16) 0.0554(7) Uani 1 1 d . . .
H11A H 0.6959 1.0423 0.5304 0.066 Uiso 1 1 calc R . .
C12 C 0.9926(4) 1.01810(17) 0.54592(15) 0.0540(6) Uani 1 1 d . . .
H12A H 1.0284 1.0343 0.4895 0.065 Uiso 1 1 calc R . .
C13 C 1.1398(4) 0.98877(17) 0.60298(14) 0.0480(6) Uani 1 1 d . . .
H13A H 1.2734 0.9849 0.5853 0.058 Uiso 1 1 calc R . .
C14 C 1.0854(3) 0.96501(14) 0.68735(14) 0.0379(5) Uani 1 1 d . . .
C15 C 1.2154(3) 0.92779(16) 0.75991(13) 0.0419(5) Uani 1 1 d . . .
H15A H 1.3051 0.9768 0.7814 0.050 Uiso 1 1 calc R . .
H15B H 1.2949 0.8739 0.7408 0.050 Uiso 1 1 calc R . .
C16 C 1.0634(3) 0.89821(14) 0.82951(13) 0.0372(5) Uani 1 1 d . . .
O3 O 0.7191(3) 0.95310(12) 0.84965(11) 0.0580(5) 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
Cl1 C4 1.737(2) . ?
O1 C8 1.220(2) . ?
O2 C7 1.405(2) . ?
O2 H2B 0.8200 . ?
C17 O3 1.210(2) . ?
C17 C9 1.462(3) . ?
C17 C16 1.541(3) . ?
F1 C16 1.396(2) . ?
N1 C8 1.343(3) . ?
N1 C1 1.404(3) . ?
N1 H1A 0.8600 . ?
C1 C2 1.377(3) . ?
C1 C6 1.389(3) . ?
C2 C3 1.383(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(3) . ?
C5 C6 1.375(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.510(3) . ?
C7 C8 1.542(3) . ?
C7 C16 1.557(3) . ?
C9 C10 1.384(3) . ?
C9 C14 1.385(3) . ?
C10 C11 1.373(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.382(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.379(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.390(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.507(3) . ?
C15 C16 1.531(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
C7 O2 H2B 109.5 . . ?
O3 C17 C9 129.1(2) . . ?
O3 C17 C16 124.1(2) . . ?
C9 C17 C16 106.84(18) . . ?
C8 N1 C1 111.94(18) . . ?
C8 N1 H1A 124.0 . . ?
C1 N1 H1A 124.0 . . ?
C2 C1 C6 121.9(2) . . ?
C2 C1 N1 128.8(2) . . ?
C6 C1 N1 109.25(19) . . ?
C1 C2 C3 117.8(2) . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 H2A 121.1 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 122.0(2) . . ?
C3 C4 Cl1 120.00(19) . . ?
C5 C4 Cl1 118.00(19) . . ?
C6 C5 C4 117.7(2) . . ?
C6 C5 H5A 121.2 . . ?
C4 C5 H5A 121.2 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 C7 131.31(19) . . ?
C1 C6 C7 108.38(18) . . ?
O2 C7 C6 112.69(17) . . ?
O2 C7 C8 111.74(16) . . ?
C6 C7 C8 101.59(16) . . ?
O2 C7 C16 109.94(17) . . ?
C6 C7 C16 110.98(16) . . ?
C8 C7 C16 109.65(16) . . ?
O1 C8 N1 126.7(2) . . ?
O1 C8 C7 125.50(19) . . ?
N1 C8 C7 107.79(17) . . ?
C10 C9 C14 122.1(2) . . ?
C10 C9 C17 128.4(2) . . ?
C14 C9 C17 109.4(2) . . ?
C11 C10 C9 118.5(2) . . ?
C11 C10 H10A 120.8 . . ?
C9 C10 H10A 120.8 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H12A 119.2 . . ?
C11 C12 H12A 119.2 . . ?
C12 C13 C14 118.9(2) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C9 C14 C13 118.8(2) . . ?
C9 C14 C15 112.30(19) . . ?
C13 C14 C15 128.9(2) . . ?
C14 C15 C16 103.63(17) . . ?
C14 C15 H15A 111.0 . . ?
C16 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
F1 C16 C15 110.91(17) . . ?
F1 C16 C17 109.40(17) . . ?
C15 C16 C17 105.40(16) . . ?
F1 C16 C7 106.48(16) . . ?
C15 C16 C7 113.04(17) . . ?
C17 C16 C7 111.64(17) . . ?

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
C8 N1 C1 C2 176.4(2) . . . . ?
C8 N1 C1 C6 -1.4(2) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
N1 C1 C2 C3 -175.8(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C2 C3 C4 Cl1 178.88(19) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
Cl1 C4 C5 C6 -179.50(16) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 -177.8(2) . . . . ?
C2 C1 C6 C5 -2.5(3) . . . . ?
N1 C1 C6 C5 175.55(18) . . . . ?
C2 C1 C6 C7 176.52(18) . . . . ?
N1 C1 C6 C7 -5.5(2) . . . . ?
C5 C6 C7 O2 -52.3(3) . . . . ?
C1 C6 C7 O2 128.89(17) . . . . ?
C5 C6 C7 C8 -172.0(2) . . . . ?
C1 C6 C7 C8 9.2(2) . . . . ?
C5 C6 C7 C16 71.5(3) . . . . ?
C1 C6 C7 C16 -107.32(19) . . . . ?
C1 N1 C8 O1 -170.8(2) . . . . ?
C1 N1 C8 C7 7.5(2) . . . . ?
O2 C7 C8 O1 48.0(3) . . . . ?
C6 C7 C8 O1 168.4(2) . . . . ?
C16 C7 C8 O1 -74.2(3) . . . . ?
O2 C7 C8 N1 -130.39(19) . . . . ?
C6 C7 C8 N1 -10.0(2) . . . . ?
C16 C7 C8 N1 107.45(19) . . . . ?
O3 C17 C9 C10 -12.6(4) . . . . ?
C16 C17 C9 C10 168.2(2) . . . . ?
O3 C17 C9 C14 168.9(2) . . . . ?
C16 C17 C9 C14 -10.3(2) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
C17 C9 C10 C11 -177.8(2) . . . . ?
C9 C10 C11 C12 -1.8(4) . . . . ?
C10 C11 C12 C13 1.8(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C10 C9 C14 C13 0.9(3) . . . . ?
C17 C9 C14 C13 179.56(19) . . . . ?
C10 C9 C14 C15 -177.7(2) . . . . ?
C17 C9 C14 C15 0.9(2) . . . . ?
C12 C13 C14 C9 -1.0(3) . . . . ?
C12 C13 C14 C15 177.4(2) . . . . ?
C9 C14 C15 C16 8.8(2) . . . . ?
C13 C14 C15 C16 -169.7(2) . . . . ?
C14 C15 C16 F1 -132.53(18) . . . . ?
C14 C15 C16 C17 -14.2(2) . . . . ?
C14 C15 C16 C7 107.97(19) . . . . ?
O3 C17 C16 F1 -44.6(3) . . . . ?
C9 C17 C16 F1 134.63(17) . . . . ?
O3 C17 C16 C15 -163.9(2) . . . . ?
C9 C17 C16 C15 15.3(2) . . . . ?
O3 C17 C16 C7 73.0(3) . . . . ?
C9 C17 C16 C7 -107.78(19) . . . . ?
O2 C7 C16 F1 -66.1(2) . . . . ?
C6 C7 C16 F1 168.55(16) . . . . ?
C8 C7 C16 F1 57.1(2) . . . . ?
O2 C7 C16 C15 55.9(2) . . . . ?
C6 C7 C16 C15 -69.4(2) . . . . ?
C8 C7 C16 C15 179.14(17) . . . . ?
O2 C7 C16 C17 174.56(16) . . . . ?
C6 C7 C16 C17 49.2(2) . . . . ?
C8 C7 C16 C17 -62.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 999612'
#######################################################################
#
#                 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_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 F N O3'
_chemical_formula_weight         299.29

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)

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

_cell_length_a                   8.1719(15)
_cell_length_b                   6.8476(12)
_cell_length_c                   12.493(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.076(7)
_cell_angle_gamma                90.00
_cell_volume                     693.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9705
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8012
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_av_sigmaI/netI    0.1342
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         24.97
_reflns_number_total             2321
_reflns_number_gt                1450
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0424P)²+0.0049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   -0.5(19)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2321
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_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
F1 F 0.7873(3) 0.8171(4) 0.7970(2) 0.0344(7) Uani 1 1 d . . .
O1 O 1.0283(4) 1.1086(4) 0.5407(2) 0.0291(8) Uani 1 1 d . . .
O2 O 0.7561(4) 0.8260(4) 0.5703(2) 0.0301(8) Uani 1 1 d . . .
H2B H 0.8315 0.8016 0.5323 0.036 Uiso 1 1 calc R . .
C1 C 0.6641(5) 1.2949(7) 0.6152(3) 0.0245(11) Uani 1 1 d . . .
O3 O 1.0112(4) 0.5973(5) 0.7214(3) 0.0415(9) Uani 1 1 d . . .
H3B H 0.9429 0.5622 0.7627 0.050 Uiso 1 1 calc R . .
C8 C 0.8964(6) 1.1407(6) 0.5762(4) 0.0265(12) Uani 1 1 d . . .
C12 C 1.0509(5) 0.7967(7) 0.7397(4) 0.0295(12) Uani 1 1 d . . .
H12A H 1.1147 0.8443 0.6814 0.035 Uiso 1 1 calc R . .
N1 N 0.8120(4) 1.3082(6) 0.5686(3) 0.0279(9) Uani 1 1 d . . .
H1A H 0.8450 1.4145 0.5379 0.033 Uiso 1 1 calc R . .
C6 C 0.6481(5) 1.1049(7) 0.6549(3) 0.0259(11) Uani 1 1 d . . .
C14 C 1.2764(6) 0.7293(7) 0.9030(4) 0.0359(13) Uani 1 1 d . . .
H14A H 1.3112 0.6112 0.8728 0.043 Uiso 1 1 calc R . .
C9 C 1.0981(6) 1.0087(7) 0.8912(4) 0.0285(12) Uani 1 1 d . . .
C15 C 1.3522(6) 0.7950(9) 1.0014(4) 0.0390(13) Uani 1 1 d . . .
H15A H 1.4393 0.7216 1.0394 0.047 Uiso 1 1 calc R . .
C5 C 0.5096(6) 1.0602(7) 0.7030(4) 0.0334(13) Uani 1 1 d . . .
H5A H 0.4955 0.9326 0.7303 0.040 Uiso 1 1 calc R . .
C10 C 0.9564(6) 1.0976(7) 0.8186(4) 0.0305(12) Uani 1 1 d . . .
H10A H 0.9936 1.2096 0.7777 0.037 Uiso 1 1 calc R . .
H10B H 0.8681 1.1417 0.8606 0.037 Uiso 1 1 calc R . .
C17 C 1.1737(6) 1.0757(8) 0.9909(4) 0.0354(13) Uani 1 1 d . . .
H17A H 1.1381 1.1933 1.0212 0.043 Uiso 1 1 calc R . .
C4 C 0.3916(6) 1.2020(8) 0.7112(4) 0.0357(13) Uani 1 1 d . . .
H4A H 0.2963 1.1711 0.7444 0.043 Uiso 1 1 calc R . .
C3 C 0.4103(6) 1.3880(7) 0.6719(4) 0.0322(13) Uani 1 1 d . . .
H3A H 0.3277 1.4835 0.6782 0.039 Uiso 1 1 calc R . .
C11 C 0.8978(5) 0.9302(7) 0.7438(4) 0.0254(12) Uani 1 1 d . . .
C2 C 0.5496(6) 1.4376(7) 0.6228(4) 0.0304(12) Uani 1 1 d . . .
H2A H 0.5638 1.5655 0.5959 0.037 Uiso 1 1 calc R . .
C13 C 1.1495(5) 0.8377(7) 0.8489(4) 0.0278(12) Uani 1 1 d . . .
C7 C 0.8001(5) 0.9898(7) 0.6357(4) 0.0248(11) Uani 1 1 d . . .
C16 C 1.3013(6) 0.9677(8) 1.0446(4) 0.0384(14) Uani 1 1 d . . .
H16A H 1.3547 1.0125 1.1120 0.046 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
F1 C11 1.416(5) . ?
O1 C8 1.235(5) . ?
O2 C7 1.408(5) . ?
O2 H2B 0.8400 . ?
C1 C2 1.365(6) . ?
C1 C6 1.405(7) . ?
C1 N1 1.408(5) . ?
O3 C12 1.416(6) . ?
O3 H3B 0.8400 . ?
C8 N1 1.336(6) . ?
C8 C7 1.544(6) . ?
C12 C13 1.523(6) . ?
C12 C11 1.556(6) . ?
C12 H12A 1.0000 . ?
N1 H1A 0.8800 . ?
C6 C5 1.380(6) . ?
C6 C7 1.515(6) . ?
C14 C15 1.382(6) . ?
C14 C13 1.382(6) . ?
C14 H14A 0.9500 . ?
C9 C13 1.372(6) . ?
C9 C17 1.398(6) . ?
C9 C10 1.508(6) . ?
C15 C16 1.385(7) . ?
C15 H15A 0.9500 . ?
C5 C4 1.382(7) . ?
C5 H5A 0.9500 . ?
C10 C11 1.519(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C17 C16 1.383(6) . ?
C17 H17A 0.9500 . ?
C4 C3 1.381(6) . ?
C4 H4A 0.9500 . ?
C3 C2 1.399(7) . ?
C3 H3A 0.9500 . ?
C11 C7 1.537(6) . ?
C2 H2A 0.9500 . ?
C16 H16A 0.9500 . ?

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
C7 O2 H2B 109.5 . . ?
C2 C1 C6 123.0(4) . . ?
C2 C1 N1 127.9(4) . . ?
C6 C1 N1 109.2(4) . . ?
C12 O3 H3B 109.5 . . ?
O1 C8 N1 126.4(4) . . ?
O1 C8 C7 125.0(4) . . ?
N1 C8 C7 108.6(4) . . ?
O3 C12 C13 114.0(4) . . ?
O3 C12 C11 113.7(4) . . ?
C13 C12 C11 101.6(4) . . ?
O3 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C8 N1 C1 112.2(4) . . ?
C8 N1 H1A 123.9 . . ?
C1 N1 H1A 123.9 . . ?
C5 C6 C1 118.5(4) . . ?
C5 C6 C7 133.3(5) . . ?
C1 C6 C7 108.2(4) . . ?
C15 C14 C13 119.1(5) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C13 C9 C17 120.1(5) . . ?
C13 C9 C10 111.2(4) . . ?
C17 C9 C10 128.7(4) . . ?
C14 C15 C16 120.1(5) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C6 C5 C4 119.6(5) . . ?
C6 C5 H5A 120.2 . . ?
C4 C5 H5A 120.2 . . ?
C9 C10 C11 103.0(4) . . ?
C9 C10 H10A 111.2 . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
C11 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
C16 C17 C9 118.7(5) . . ?
C16 C17 H17A 120.6 . . ?
C9 C17 H17A 120.6 . . ?
C3 C4 C5 120.9(5) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
F1 C11 C10 107.1(4) . . ?
F1 C11 C7 105.4(3) . . ?
C10 C11 C7 115.5(4) . . ?
F1 C11 C12 104.9(4) . . ?
C10 C11 C12 105.7(4) . . ?
C7 C11 C12 117.4(4) . . ?
C1 C2 C3 117.3(5) . . ?
C1 C2 H2A 121.3 . . ?
C3 C2 H2A 121.3 . . ?
C9 C13 C14 121.1(5) . . ?
C9 C13 C12 110.4(4) . . ?
C14 C13 C12 128.4(4) . . ?
O2 C7 C6 110.5(4) . . ?
O2 C7 C11 111.5(4) . . ?
C6 C7 C11 110.3(4) . . ?
O2 C7 C8 111.3(4) . . ?
C6 C7 C8 101.8(4) . . ?
C11 C7 C8 111.1(4) . . ?
C17 C16 C15 120.8(5) . . ?
C17 C16 H16A 119.6 . . ?
C15 C16 H16A 119.6 . . ?

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 C8 N1 C1 178.5(4) . . . . ?
C7 C8 N1 C1 -0.5(5) . . . . ?
C2 C1 N1 C8 179.2(5) . . . . ?
C6 C1 N1 C8 -1.0(5) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
N1 C1 C6 C5 -179.3(4) . . . . ?
C2 C1 C6 C7 -178.1(4) . . . . ?
N1 C1 C6 C7 2.1(5) . . . . ?
C13 C14 C15 C16 -0.2(7) . . . . ?
C1 C6 C5 C4 -0.2(7) . . . . ?
C7 C6 C5 C4 178.0(5) . . . . ?
C13 C9 C10 C11 15.5(5) . . . . ?
C17 C9 C10 C11 -162.8(5) . . . . ?
C13 C9 C17 C16 0.7(7) . . . . ?
C10 C9 C17 C16 178.9(5) . . . . ?
C6 C5 C4 C3 0.0(7) . . . . ?
C5 C4 C3 C2 -0.1(8) . . . . ?
C9 C10 C11 F1 84.9(4) . . . . ?
C9 C10 C11 C7 -158.0(4) . . . . ?
C9 C10 C11 C12 -26.5(5) . . . . ?
O3 C12 C11 F1 37.5(5) . . . . ?
C13 C12 C11 F1 -85.5(4) . . . . ?
O3 C12 C11 C10 150.5(4) . . . . ?
C13 C12 C11 C10 27.5(5) . . . . ?
O3 C12 C11 C7 -79.1(5) . . . . ?
C13 C12 C11 C7 157.9(4) . . . . ?
C6 C1 C2 C3 -0.6(7) . . . . ?
N1 C1 C2 C3 179.2(4) . . . . ?
C4 C3 C2 C1 0.4(7) . . . . ?
C17 C9 C13 C14 -0.4(7) . . . . ?
C10 C9 C13 C14 -178.9(4) . . . . ?
C17 C9 C13 C12 -179.2(4) . . . . ?
C10 C9 C13 C12 2.3(5) . . . . ?
C15 C14 C13 C9 0.1(7) . . . . ?
C15 C14 C13 C12 178.7(4) . . . . ?
O3 C12 C13 C9 -141.4(4) . . . . ?
C11 C12 C13 C9 -18.6(5) . . . . ?
O3 C12 C13 C14 39.9(7) . . . . ?
C11 C12 C13 C14 162.7(5) . . . . ?
C5 C6 C7 O2 61.1(7) . . . . ?
C1 C6 C7 O2 -120.5(4) . . . . ?
C5 C6 C7 C11 -62.6(7) . . . . ?
C1 C6 C7 C11 115.8(4) . . . . ?
C5 C6 C7 C8 179.4(5) . . . . ?
C1 C6 C7 C8 -2.3(5) . . . . ?
F1 C11 C7 O2 -64.1(4) . . . . ?
C10 C11 C7 O2 177.9(4) . . . . ?
C12 C11 C7 O2 52.2(5) . . . . ?
F1 C11 C7 C6 59.1(4) . . . . ?
C10 C11 C7 C6 -59.0(5) . . . . ?
C12 C11 C7 C6 175.3(4) . . . . ?
F1 C11 C7 C8 171.2(3) . . . . ?
C10 C11 C7 C8 53.2(5) . . . . ?
C12 C11 C7 C8 -72.5(5) . . . . ?
O1 C8 C7 O2 -59.6(6) . . . . ?
N1 C8 C7 O2 119.4(4) . . . . ?
O1 C8 C7 C6 -177.4(4) . . . . ?
N1 C8 C7 C6 1.7(5) . . . . ?
O1 C8 C7 C11 65.2(6) . . . . ?
N1 C8 C7 C11 -115.7(4) . . . . ?
C9 C17 C16 C15 -0.8(7) . . . . ?
C14 C15 C16 C17 0.6(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 999613'
