# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_8ba
_database_code_depnum_ccdc_archive 'CCDC 1446158'
_audit_update_record             
;
2016-01-08 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Rac-(2R,4R,5R)-tert-butyl 2-(4-chlorophenyl)-4-fluoro-5-hydroxypiperidine-1-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          '108--109 ?C'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 Cl F N O3'
_chemical_formula_weight         329.79

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'
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'
N N 0.0061 0.0033 '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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.2113(8)
_cell_length_b                   10.8594(9)
_cell_length_c                   15.4503(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.9460(10)
_cell_angle_gamma                90.00
_cell_volume                     1669.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5654
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9378
_exptl_absorpt_correction_T_max  0.9706
_exptl_absorpt_process_details   ?

_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            12506
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3084
_reflns_number_gt                2514
_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)+(0.0592P)²+0.7813P] 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     SHELXL
_refine_ls_extinction_coef       0.0020(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3084
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.004
_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 0.29284(7) 0.37102(8) -0.00528(4) 0.0846(3) Uani 1 1 d . . .
C5 C 0.59816(17) 0.56114(17) 0.20983(12) 0.0410(4) Uani 1 1 d . . .
C6 C 0.4919(2) 0.62569(19) 0.15774(13) 0.0494(5) Uani 1 1 d . . .
H6 H 0.4831 0.7094 0.1679 0.059 Uiso 1 1 calc R . .
C7 C 0.3990(2) 0.5685(2) 0.09127(14) 0.0557(5) Uani 1 1 d . . .
H7 H 0.3281 0.6130 0.0571 0.067 Uiso 1 1 calc R . .
C2 C 0.4127(2) 0.4450(2) 0.07619(13) 0.0556(5) Uani 1 1 d . . .
C3 C 0.5189(2) 0.3795(2) 0.12414(15) 0.0594(6) Uani 1 1 d . . .
H3 H 0.5289 0.2965 0.1122 0.071 Uiso 1 1 calc R . .
C4 C 0.6109(2) 0.43784(19) 0.19028(14) 0.0521(5) Uani 1 1 d . . .
H4 H 0.6834 0.3933 0.2226 0.063 Uiso 1 1 calc R . .
C8 C 0.70020(18) 0.62847(16) 0.28106(13) 0.0442(4) Uani 1 1 d . . .
H8 H 0.7443 0.6893 0.2503 0.053 Uiso 1 1 calc R . .
N1 N 0.80664(15) 0.54796(15) 0.33071(11) 0.0470(4) Uani 1 1 d . . .
C11 C 0.6021(2) 0.6239(2) 0.41953(15) 0.0611(6) Uani 1 1 d . . .
H11 H 0.5717 0.6778 0.4620 0.073 Uiso 1 1 calc R . .
C12 C 0.6356(2) 0.70055(19) 0.34655(14) 0.0552(5) Uani 1 1 d . . .
H12A H 0.6966 0.7656 0.3731 0.066 Uiso 1 1 calc R . .
H12B H 0.5539 0.7392 0.3136 0.066 Uiso 1 1 calc R . .
C9 C 0.7750(2) 0.47270(19) 0.40198(14) 0.0534(5) Uani 1 1 d . . .
H9A H 0.8554 0.4300 0.4328 0.064 Uiso 1 1 calc R . .
H9B H 0.7086 0.4112 0.3765 0.064 Uiso 1 1 calc R . .
C10 C 0.7216(2) 0.5503(2) 0.46743(14) 0.0593(6) Uani 1 1 d . . .
H10 H 0.6947 0.4967 0.5115 0.071 Uiso 1 1 calc R . .
F1 F 0.49943(12) 0.53969(15) 0.38378(9) 0.0735(4) Uani 1 1 d . . .
C13 C 0.92678(18) 0.53339(18) 0.30933(13) 0.0462(5) Uani 1 1 d . . .
O1 O 1.00928(14) 0.45631(15) 0.34373(11) 0.0658(5) Uani 1 1 d . . .
O2 O 0.94468(12) 0.61197(13) 0.24657(9) 0.0518(4) Uani 1 1 d . . .
C14 C 1.0702(2) 0.6107(2) 0.21288(15) 0.0553(5) Uani 1 1 d . . .
C17 C 1.1911(2) 0.6346(3) 0.28714(19) 0.0809(8) Uani 1 1 d . . .
H17A H 1.2680 0.6500 0.2627 0.121 Uiso 1 1 calc R . .
H17B H 1.2078 0.5639 0.3253 0.121 Uiso 1 1 calc R . .
H17C H 1.1743 0.7049 0.3207 0.121 Uiso 1 1 calc R . .
C16 C 1.0490(3) 0.7185(3) 0.14935(18) 0.0788(8) Uani 1 1 d . . .
H16A H 0.9694 0.7050 0.1037 0.118 Uiso 1 1 calc R . .
H16B H 1.1251 0.7263 0.1228 0.118 Uiso 1 1 calc R . .
H16C H 1.0389 0.7926 0.1811 0.118 Uiso 1 1 calc R . .
C15 C 1.0774(3) 0.4913(3) 0.1644(2) 0.0941(10) Uani 1 1 d . . .
H15A H 1.1484 0.4958 0.1330 0.141 Uiso 1 1 calc R . .
H15B H 0.9935 0.4772 0.1230 0.141 Uiso 1 1 calc R . .
H15C H 1.0948 0.4248 0.2064 0.141 Uiso 1 1 calc R . .
O3 O 0.8173(2) 0.63698(16) 0.51127(13) 0.0831(6) Uani 1 1 d . . .
H3A H 0.7952 0.7062 0.4923 0.125 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
Cl1 C2 1.743(2) . ?
C5 C4 1.385(3) . ?
C5 C6 1.387(3) . ?
C5 C8 1.522(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
C7 C2 1.374(3) . ?
C7 H7 0.9300 . ?
C2 C3 1.368(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C8 N1 1.470(2) . ?
C8 C12 1.540(3) . ?
C8 H8 0.9800 . ?
N1 C13 1.349(2) . ?
N1 C9 1.464(2) . ?
C11 F1 1.407(3) . ?
C11 C12 1.502(3) . ?
C11 C10 1.507(3) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 C10 1.509(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O3 1.416(3) . ?
C10 H10 0.9800 . ?
C13 O1 1.222(2) . ?
C13 O2 1.335(2) . ?
O2 C14 1.488(2) . ?
C14 C15 1.508(3) . ?
C14 C17 1.507(3) . ?
C14 C16 1.511(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O3 H3A 0.8200 . ?

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
C4 C5 C6 117.48(18) . . ?
C4 C5 C8 122.64(17) . . ?
C6 C5 C8 119.76(17) . . ?
C7 C6 C5 121.50(19) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C2 C7 C6 119.11(19) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C3 C2 C7 120.9(2) . . ?
C3 C2 Cl1 119.66(18) . . ?
C7 C2 Cl1 119.40(18) . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 121.62(19) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
N1 C8 C5 113.45(15) . . ?
N1 C8 C12 109.57(16) . . ?
C5 C8 C12 113.25(15) . . ?
N1 C8 H8 106.7 . . ?
C5 C8 H8 106.7 . . ?
C12 C8 H8 106.7 . . ?
C13 N1 C9 118.98(16) . . ?
C13 N1 C8 123.27(15) . . ?
C9 N1 C8 117.55(15) . . ?
F1 C11 C12 109.92(18) . . ?
F1 C11 C10 107.36(19) . . ?
C12 C11 C10 111.52(18) . . ?
F1 C11 H11 109.3 . . ?
C12 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
C11 C12 C8 114.52(17) . . ?
C11 C12 H12A 108.6 . . ?
C8 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C8 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
N1 C9 C10 111.48(17) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
O3 C10 C11 106.20(19) . . ?
O3 C10 C9 112.15(19) . . ?
C11 C10 C9 109.97(18) . . ?
O3 C10 H10 109.5 . . ?
C11 C10 H10 109.5 . . ?
C9 C10 H10 109.5 . . ?
O1 C13 O2 124.12(18) . . ?
O1 C13 N1 123.37(18) . . ?
O2 C13 N1 112.51(16) . . ?
C13 O2 C14 121.16(15) . . ?
O2 C14 C15 108.86(18) . . ?
O2 C14 C17 110.78(18) . . ?
C15 C14 C17 113.8(2) . . ?
O2 C14 C16 102.17(17) . . ?
C15 C14 C16 111.1(2) . . ?
C17 C14 C16 109.6(2) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 O3 H3A 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
C4 C5 C6 C7 2.6(3) . . . . ?
C8 C5 C6 C7 178.60(17) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C6 C7 C2 C3 -2.0(3) . . . . ?
C6 C7 C2 Cl1 177.98(15) . . . . ?
C7 C2 C3 C4 2.0(3) . . . . ?
Cl1 C2 C3 C4 -177.99(17) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C6 C5 C4 C3 -2.6(3) . . . . ?
C8 C5 C4 C3 -178.50(19) . . . . ?
C4 C5 C8 N1 -4.3(3) . . . . ?
C6 C5 C8 N1 179.97(16) . . . . ?
C4 C5 C8 C12 -129.98(19) . . . . ?
C6 C5 C8 C12 54.3(2) . . . . ?
C5 C8 N1 C13 94.6(2) . . . . ?
C12 C8 N1 C13 -137.79(19) . . . . ?
C5 C8 N1 C9 -80.2(2) . . . . ?
C12 C8 N1 C9 47.5(2) . . . . ?
F1 C11 C12 C8 -66.7(2) . . . . ?
C10 C11 C12 C8 52.3(2) . . . . ?
N1 C8 C12 C11 -46.1(2) . . . . ?
C5 C8 C12 C11 81.6(2) . . . . ?
C13 N1 C9 C10 131.29(19) . . . . ?
C8 N1 C9 C10 -53.8(2) . . . . ?
F1 C11 C10 O3 -173.39(18) . . . . ?
C12 C11 C10 O3 66.1(2) . . . . ?
F1 C11 C10 C9 65.1(2) . . . . ?
C12 C11 C10 C9 -55.4(2) . . . . ?
N1 C9 C10 O3 -62.8(2) . . . . ?
N1 C9 C10 C11 55.2(2) . . . . ?
C9 N1 C13 O1 3.4(3) . . . . ?
C8 N1 C13 O1 -171.25(19) . . . . ?
C9 N1 C13 O2 -176.82(17) . . . . ?
C8 N1 C13 O2 8.5(3) . . . . ?
O1 C13 O2 C14 0.2(3) . . . . ?
N1 C13 O2 C14 -179.54(17) . . . . ?
C13 O2 C14 C15 66.2(3) . . . . ?
C13 O2 C14 C17 -59.6(3) . . . . ?
C13 O2 C14 C16 -176.26(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_aaa
_database_code_depnum_ccdc_archive 'CCDC 1446172'
_audit_update_record             
;
2016-01-08 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Rac-(2R,4R,5R)-tert-butyl 4-fluoro-5-hydroxy-2-(p-tolyl)piperidine-1-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         102-104
_chemical_formula_sum            'C17 H24 F N O3'
_chemical_formula_weight         309.37

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)/n

loop_
_symmetry_equiv_pos_as_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                   10.0718(18)
_cell_length_b                   10.9443(19)
_cell_length_c                   15.782(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.965(2)
_cell_angle_gamma                90.00
_cell_volume                     1695.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3343
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      28.03

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9771
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_process_details   ?

_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            12730
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3159
_reflns_number_gt                2250
_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)+(0.0687P)²+0.2015P] 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_number_reflns         3159
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.001

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
C4 C 0.89814(15) 0.06665(14) 0.28370(10) 0.0393(4) Uani 1 1 d . . .
C5 C 1.00518(17) 0.13001(16) 0.33574(11) 0.0475(4) Uani 1 1 d . . .
H5 H 1.0167 0.2125 0.3252 0.057 Uiso 1 1 calc R . .
C1 C 1.08255(18) -0.04961(18) 0.42057(11) 0.0535(5) Uani 1 1 d . . .
C3 C 0.88293(18) -0.05449(16) 0.30379(11) 0.0497(4) Uani 1 1 d . . .
H3 H 0.8102 -0.0988 0.2715 0.060 Uiso 1 1 calc R . .
C6 C 1.09492(18) 0.07280(19) 0.40282(11) 0.0550(5) Uani 1 1 d . . .
H6 H 1.1655 0.1178 0.4369 0.066 Uiso 1 1 calc R . .
C2 C 0.9735(2) -0.11111(18) 0.37084(12) 0.0567(5) Uani 1 1 d . . .
H2 H 0.9604 -0.1929 0.3827 0.068 Uiso 1 1 calc R . .
C7 C 0.79884(15) 0.13320(14) 0.21200(11) 0.0425(4) Uani 1 1 d . . .
H7 H 0.7544 0.1956 0.2406 0.051 Uiso 1 1 calc R . .
C10 C 0.90058(19) 0.12233(19) 0.07781(12) 0.0617(5) Uani 1 1 d . . .
H10 H 0.9336 0.1742 0.0363 0.074 Uiso 1 1 calc R . .
C8 C 0.72047(18) -0.02204(16) 0.09443(12) 0.0528(5) Uani 1 1 d . . .
H8A H 0.6377 -0.0622 0.0638 0.063 Uiso 1 1 calc R . .
H8B H 0.7854 -0.0848 0.1198 0.063 Uiso 1 1 calc R . .
C11 C 0.86688(18) 0.20076(17) 0.14817(11) 0.0540(5) Uani 1 1 d . . .
H11A H 0.8069 0.2661 0.1212 0.065 Uiso 1 1 calc R . .
H11B H 0.9503 0.2380 0.1806 0.065 Uiso 1 1 calc R . .
C9 C 0.7784(2) 0.05238(18) 0.03089(12) 0.0596(5) Uani 1 1 d . . .
H9 H 0.8046 -0.0022 -0.0118 0.072 Uiso 1 1 calc R . .
N1 N 0.69009(13) 0.05433(13) 0.16372(9) 0.0453(4) Uani 1 1 d . . .
C12 C 0.56988(16) 0.03917(15) 0.18616(11) 0.0467(4) Uani 1 1 d . . .
O2 O 0.55622(11) 0.11423(11) 0.25058(8) 0.0527(3) Uani 1 1 d . . .
O1 O 0.48419(13) -0.03480(13) 0.15237(9) 0.0690(4) Uani 1 1 d . . .
C13 C 0.42975(17) 0.11493(17) 0.28373(12) 0.0545(5) Uani 1 1 d . . .
C14 C 0.3093(2) 0.1481(2) 0.21300(16) 0.0812(7) Uani 1 1 d . . .
H14A H 0.3273 0.2233 0.1863 0.122 Uiso 1 1 calc R . .
H14B H 0.2306 0.1580 0.2372 0.122 Uiso 1 1 calc R . .
H14C H 0.2927 0.0844 0.1701 0.122 Uiso 1 1 calc R . .
C16 C 0.4589(2) 0.2160(2) 0.35073(14) 0.0815(7) Uani 1 1 d . . .
H16A H 0.5410 0.1976 0.3929 0.122 Uiso 1 1 calc R . .
H16B H 0.3844 0.2226 0.3792 0.122 Uiso 1 1 calc R . .
H16C H 0.4696 0.2919 0.3226 0.122 Uiso 1 1 calc R . .
C15 C 0.4146(3) -0.0061(2) 0.3260(2) 0.0958(8) Uani 1 1 d . . .
H15A H 0.3957 -0.0687 0.2824 0.144 Uiso 1 1 calc R . .
H15B H 0.3410 -0.0015 0.3554 0.144 Uiso 1 1 calc R . .
H15C H 0.4976 -0.0253 0.3673 0.144 Uiso 1 1 calc R . .
O3 O 0.68511(17) 0.14091(13) -0.01285(10) 0.0842(5) Uani 1 1 d . . .
H3A H 0.6291 0.1078 -0.0519 0.126 Uiso 1 1 calc R . .
F1 F 1.00172(11) 0.03744(12) 0.11376(8) 0.0757(4) Uani 1 1 d . . .
C17 C 1.1837(2) -0.1121(2) 0.49163(13) 0.0781(7) Uani 1 1 d . . .
H17A H 1.2687 -0.1211 0.4743 0.117 Uiso 1 1 calc R . .
H17B H 1.1497 -0.1913 0.5023 0.117 Uiso 1 1 calc R . .
H17C H 1.1975 -0.0640 0.5437 0.117 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
C4 C3 1.380(2) . ?
C4 C5 1.386(2) . ?
C4 C7 1.518(2) . ?
C5 C6 1.379(2) . ?
C5 H5 0.9300 . ?
C1 C6 1.380(3) . ?
C1 C2 1.374(3) . ?
C1 C17 1.501(3) . ?
C3 C2 1.379(2) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C7 N1 1.467(2) . ?
C7 C11 1.530(2) . ?
C7 H7 0.9800 . ?
C10 F1 1.401(2) . ?
C10 C9 1.497(3) . ?
C10 C11 1.501(3) . ?
C10 H10 0.9800 . ?
C8 N1 1.462(2) . ?
C8 C9 1.507(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C9 O3 1.417(2) . ?
C9 H9 0.9800 . ?
N1 C12 1.346(2) . ?
C12 O1 1.216(2) . ?
C12 O2 1.338(2) . ?
O2 C13 1.4817(18) . ?
C13 C14 1.498(3) . ?
C13 C15 1.506(3) . ?
C13 C16 1.512(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O3 H3A 0.8200 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C3 C4 C5 117.16(15) . . ?
C3 C4 C7 122.95(14) . . ?
C5 C4 C7 119.78(14) . . ?
C6 C5 C4 121.11(17) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C6 C1 C2 117.16(17) . . ?
C6 C1 C17 121.16(19) . . ?
C2 C1 C17 121.69(19) . . ?
C2 C3 C4 121.31(16) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C1 C6 C5 121.56(17) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C3 C2 C1 121.62(18) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
N1 C7 C4 113.29(13) . . ?
N1 C7 C11 109.57(13) . . ?
C4 C7 C11 113.91(13) . . ?
N1 C7 H7 106.5 . . ?
C4 C7 H7 106.5 . . ?
C11 C7 H7 106.5 . . ?
F1 C10 C9 107.68(16) . . ?
F1 C10 C11 110.12(15) . . ?
C9 C10 C11 111.16(15) . . ?
F1 C10 H10 109.3 . . ?
C9 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
N1 C8 C9 111.46(15) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C11 C7 114.82(15) . . ?
C10 C11 H11A 108.6 . . ?
C7 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C7 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
O3 C9 C10 105.84(16) . . ?
O3 C9 C8 112.38(16) . . ?
C10 C9 C8 110.20(15) . . ?
O3 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C12 N1 C8 118.54(14) . . ?
C12 N1 C7 123.16(13) . . ?
C8 N1 C7 117.89(12) . . ?
O1 C12 N1 123.97(16) . . ?
O1 C12 O2 123.94(15) . . ?
N1 C12 O2 112.09(14) . . ?
C12 O2 C13 120.97(13) . . ?
O2 C13 C14 110.79(15) . . ?
O2 C13 C15 109.41(15) . . ?
C14 C13 C15 113.46(19) . . ?
O2 C13 C16 101.74(14) . . ?
C14 C13 C16 109.95(17) . . ?
C15 C13 C16 110.87(19) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 O3 H3A 109.5 . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C3 C4 C5 C6 2.1(2) . . . . ?
C7 C4 C5 C6 178.29(14) . . . . ?
C5 C4 C3 C2 -2.3(2) . . . . ?
C7 C4 C3 C2 -178.39(15) . . . . ?
C2 C1 C6 C5 -2.7(2) . . . . ?
C17 C1 C6 C5 177.73(15) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C6 C1 C2 C3 2.4(3) . . . . ?
C17 C1 C2 C3 -177.96(16) . . . . ?
C3 C4 C7 N1 -3.0(2) . . . . ?
C5 C4 C7 N1 -179.00(12) . . . . ?
C3 C4 C7 C11 -129.17(16) . . . . ?
C5 C4 C7 C11 54.86(19) . . . . ?
F1 C10 C11 C7 -66.55(19) . . . . ?
C9 C10 C11 C7 52.7(2) . . . . ?
N1 C7 C11 C10 -45.93(19) . . . . ?
C4 C7 C11 C10 82.14(18) . . . . ?
F1 C10 C9 O3 -173.26(14) . . . . ?
C11 C10 C9 O3 66.04(19) . . . . ?
F1 C10 C9 C8 64.99(18) . . . . ?
C11 C10 C9 C8 -55.7(2) . . . . ?
N1 C8 C9 O3 -62.84(19) . . . . ?
N1 C8 C9 C10 54.9(2) . . . . ?
C9 C8 N1 C12 134.41(16) . . . . ?
C9 C8 N1 C7 -52.7(2) . . . . ?
C4 C7 N1 C12 90.72(18) . . . . ?
C11 C7 N1 C12 -140.87(16) . . . . ?
C4 C7 N1 C8 -81.85(17) . . . . ?
C11 C7 N1 C8 46.56(19) . . . . ?
C8 N1 C12 O1 0.2(3) . . . . ?
C7 N1 C12 O1 -172.35(17) . . . . ?
C8 N1 C12 O2 179.58(14) . . . . ?
C7 N1 C12 O2 7.1(2) . . . . ?
O1 C12 O2 C13 -2.2(3) . . . . ?
N1 C12 O2 C13 178.36(14) . . . . ?
C12 O2 C13 C14 -60.4(2) . . . . ?
C12 O2 C13 C15 65.4(2) . . . . ?
C12 O2 C13 C16 -177.26(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
