# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_exp_281
_database_code_depnum_ccdc_archive 'CCDC 1887247'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2018-12-25 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3-{[2-(Dimethylamino)ethyl]amino}-5-hydroxy-5-(trifluoromethyl)cyclohex-2-en-1-one
_chemical_name_common            ?
_chemical_melting_point          459-461
_chemical_formula_moiety         'C11 H17 F3 N2 O2'
_chemical_formula_sum            'C11 H17 F3 N2 O2'
_chemical_formula_weight         266.27

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0958(6)
_cell_length_b                   8.4262(7)
_cell_length_c                   11.3160(8)
_cell_angle_alpha                87.424(6)
_cell_angle_beta                 82.903(6)
_cell_angle_gamma                75.668(7)
_cell_volume                     650.44(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    145(2)
_cell_measurement_reflns_used    1200
_cell_measurement_theta_min      3.6450
_cell_measurement_theta_max      30.0160

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_min  0.85675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      145(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       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.5253
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5313
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0908
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         30.80
_reflns_number_total             3488
_reflns_number_gt                2016
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0900P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3488
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.2089
_refine_ls_wR_factor_gt          0.1552
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.0923(3) 0.3142(2) 0.71486(16) 0.0288(4) Uani 1 1 d . . .
F1 F 0.1245(3) 0.07011(19) 0.55528(14) 0.0429(5) Uani 1 1 d . . .
N1 N 0.2796(3) 0.4908(2) 1.30560(18) 0.0285(5) Uani 1 1 d . . .
C1 C 0.1158(4) 0.1494(3) 0.7551(2) 0.0245(5) Uani 1 1 d . . .
F2 F 0.4005(2) 0.0695(2) 0.61607(14) 0.0429(4) Uani 1 1 d . . .
N2 N 0.2479(3) 0.2618(2) 1.03627(18) 0.0257(5) Uani 1 1 d . . .
O2 O -0.3591(3) 0.2053(2) 0.93420(18) 0.0377(5) Uani 1 1 d . . .
C2 C -0.0791(4) 0.1076(3) 0.7970(2) 0.0275(5) Uani 1 1 d . . .
H2A H -0.1660 0.1412 0.7358 0.033 Uiso 1 1 calc R . .
H2B H -0.0569 -0.0102 0.8074 0.033 Uiso 1 1 calc R . .
F3 F 0.2521(3) -0.11833(18) 0.67730(15) 0.0448(5) Uani 1 1 d . . .
C3 C -0.1782(3) 0.1886(3) 0.9125(2) 0.0267(5) Uani 1 1 d . . .
C4 C -0.0648(4) 0.2399(3) 0.9908(2) 0.0254(5) Uani 1 1 d . . .
C5 C 0.1348(3) 0.2148(3) 0.9659(2) 0.0223(5) Uani 1 1 d . . .
C6 C 0.2426(3) 0.1210(3) 0.8573(2) 0.0244(5) Uani 1 1 d . . .
H6A H 0.2783 0.0050 0.8769 0.029 Uiso 1 1 calc R . .
H6B H 0.3621 0.1559 0.8326 0.029 Uiso 1 1 calc R . .
C7 C 0.2232(4) 0.0433(3) 0.6510(2) 0.0320(6) Uani 1 1 d . . .
C8 C 0.1742(4) 0.3480(3) 1.1468(2) 0.0264(5) Uani 1 1 d . . .
H8A H 0.1201 0.2776 1.2044 0.032 Uiso 1 1 calc R . .
H8B H 0.0713 0.4445 1.1330 0.032 Uiso 1 1 calc R . .
C9 C 0.3431(4) 0.3981(3) 1.1944(2) 0.0267(5) Uani 1 1 d . . .
H9A H 0.4443 0.3006 1.2087 0.032 Uiso 1 1 calc R . .
H9B H 0.3994 0.4648 1.1347 0.032 Uiso 1 1 calc R . .
C10 C 0.4400(4) 0.5619(3) 1.3320(3) 0.0386(7) Uani 1 1 d . . .
H10A H 0.3989 0.6265 1.4025 0.058 Uiso 1 1 calc R . .
H10B H 0.4726 0.6300 1.2662 0.058 Uiso 1 1 calc R . .
H10C H 0.5528 0.4753 1.3443 0.058 Uiso 1 1 calc R . .
C11 C 0.2333(4) 0.3838(3) 1.4053(2) 0.0391(7) Uani 1 1 d . . .
H11A H 0.1234 0.3432 1.3908 0.059 Uiso 1 1 calc R . .
H11B H 0.2018 0.4449 1.4777 0.059 Uiso 1 1 calc R . .
H11C H 0.3445 0.2935 1.4125 0.059 Uiso 1 1 calc R . .
H4 H -0.128(4) 0.291(3) 1.061(3) 0.033(7) Uiso 1 1 d . . .
H2 H 0.380(5) 0.248(3) 1.009(2) 0.033(7) Uiso 1 1 d . . .
H17 H -0.039(6) 0.370(4) 0.706(3) 0.060(10) Uiso 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 C1 1.418(3) . ?
O1 H17 0.95(4) . ?
F1 C7 1.342(3) . ?
N1 C11 1.468(3) . ?
N1 C9 1.474(3) . ?
N1 C10 1.477(3) . ?
C1 C7 1.518(3) . ?
C1 C2 1.525(3) . ?
C1 C6 1.527(3) . ?
F2 C7 1.340(3) . ?
N2 C5 1.333(3) . ?
N2 C8 1.448(3) . ?
N2 H2 0.93(3) . ?
O2 C3 1.250(3) . ?
C2 C3 1.511(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
F3 C7 1.351(3) . ?
C3 C4 1.415(3) . ?
C4 C5 1.374(3) . ?
C4 H4 0.93(3) . ?
C5 C6 1.509(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.528(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C1 O1 H17 114.1(19) . . ?
C11 N1 C9 111.00(19) . . ?
C11 N1 C10 109.2(2) . . ?
C9 N1 C10 108.4(2) . . ?
O1 C1 C7 106.42(19) . . ?
O1 C1 C2 112.6(2) . . ?
C7 C1 C2 110.54(19) . . ?
O1 C1 C6 108.50(18) . . ?
C7 C1 C6 109.2(2) . . ?
C2 C1 C6 109.5(2) . . ?
C5 N2 C8 123.9(2) . . ?
C5 N2 H2 118.1(17) . . ?
C8 N2 H2 117.6(17) . . ?
C3 C2 C1 113.23(19) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
O2 C3 C4 123.2(2) . . ?
O2 C3 C2 117.3(2) . . ?
C4 C3 C2 119.5(2) . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 H4 119.7(18) . . ?
C3 C4 H4 118.6(18) . . ?
N2 C5 C4 124.0(2) . . ?
N2 C5 C6 115.2(2) . . ?
C4 C5 C6 120.7(2) . . ?
C5 C6 C1 110.89(19) . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
F2 C7 F1 106.8(2) . . ?
F2 C7 F3 106.3(2) . . ?
F1 C7 F3 106.37(19) . . ?
F2 C7 C1 112.3(2) . . ?
F1 C7 C1 112.2(2) . . ?
F3 C7 C1 112.3(2) . . ?
N2 C8 C9 108.6(2) . . ?
N2 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N2 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.3 . . ?
N1 C9 C8 112.2(2) . . ?
N1 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O1 C1 C2 C3 -70.5(3) . . . . ?
C7 C1 C2 C3 170.6(2) . . . . ?
C6 C1 C2 C3 50.2(3) . . . . ?
C1 C2 C3 O2 157.9(2) . . . . ?
C1 C2 C3 C4 -22.8(3) . . . . ?
O2 C3 C4 C5 177.8(2) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C8 N2 C5 C4 -1.2(4) . . . . ?
C8 N2 C5 C6 -177.8(2) . . . . ?
C3 C4 C5 N2 179.5(2) . . . . ?
C3 C4 C5 C6 -4.1(4) . . . . ?
N2 C5 C6 C1 -150.3(2) . . . . ?
C4 C5 C6 C1 33.0(3) . . . . ?
O1 C1 C6 C5 68.6(2) . . . . ?
C7 C1 C6 C5 -175.74(19) . . . . ?
C2 C1 C6 C5 -54.6(2) . . . . ?
O1 C1 C7 F2 61.2(3) . . . . ?
C2 C1 C7 F2 -176.3(2) . . . . ?
C6 C1 C7 F2 -55.8(3) . . . . ?
O1 C1 C7 F1 -59.2(3) . . . . ?
C2 C1 C7 F1 63.4(3) . . . . ?
C6 C1 C7 F1 -176.11(19) . . . . ?
O1 C1 C7 F3 -178.9(2) . . . . ?
C2 C1 C7 F3 -56.4(3) . . . . ?
C6 C1 C7 F3 64.1(3) . . . . ?
C5 N2 C8 C9 -173.5(2) . . . . ?
C11 N1 C9 C8 71.1(3) . . . . ?
C10 N1 C9 C8 -168.9(2) . . . . ?
N2 C8 C9 N1 178.49(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.856
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_dc
_database_code_depnum_ccdc_archive 'CCDC 1887248'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2018-12-25 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Pyrrolidinium 5-Hydroxy-2-propyl-5-(trifluoromethyl)cyclohex-1-one-3-olate'
_chemical_name_common            ?
_chemical_melting_point          442-444
_chemical_formula_moiety         'C4 H10 N, C10 H12 F3 O3'
_chemical_formula_sum            'C14 H22 F3 N O3'
_chemical_formula_weight         309.33

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                   9.1257(9)
_cell_length_b                   21.064(2)
_cell_length_c                   8.9372(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.891(14)
_cell_angle_gamma                90.00
_cell_volume                     1518.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1840
_cell_measurement_theta_min      3.8960
_cell_measurement_theta_max      28.2840

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_min  0.82049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.5253
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9806
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         30.93
_reflns_number_total             4151
_reflns_number_gt                2105
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1100P)²+0.2800P] 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       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4151
_refine_ls_number_parameters     228
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.2429
_refine_ls_wR_factor_gt          0.1804
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.018
_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
O2 O 0.18036(18) 0.54046(9) 0.2549(2) 0.0631(5) Uani 1 1 d . . .
C6 C 0.0422(2) 0.52856(12) 0.2534(3) 0.0543(6) Uani 1 1 d . . .
O1 O -0.2927(2) 0.49253(10) -0.0356(2) 0.0651(5) Uani 1 1 d . . .
C7 C -0.0403(3) 0.57221(13) 0.3039(3) 0.0578(6) Uani 1 1 d . B .
O3 O -0.2607(2) 0.59137(12) 0.3617(3) 0.0891(7) Uani 1 1 d . . .
F1 F -0.2310(3) 0.36190(9) -0.0161(3) 0.0977(6) Uani 1 1 d . . .
N1 N -0.5240(3) 0.60842(11) -0.5900(3) 0.0604(6) Uani 1 1 d . . .
F2 F -0.4402(2) 0.38815(11) 0.0170(3) 0.1128(8) Uani 1 1 d . . .
C10 C -0.2148(3) 0.45994(14) 0.1204(3) 0.0611(7) Uani 1 1 d . . .
C9 C -0.2670(3) 0.49164(15) 0.2410(3) 0.0693(8) Uani 1 1 d . . .
H9A H -0.3866 0.4965 0.1837 0.083 Uiso 1 1 calc R . .
H9B H -0.2384 0.4638 0.3373 0.083 Uiso 1 1 calc R . .
C11 C -0.0257(3) 0.46275(13) 0.1975(3) 0.0594(6) Uani 1 1 d . . .
H11A H 0.0228 0.4344 0.2941 0.071 Uiso 1 1 calc R . .
H11B H 0.0067 0.4479 0.1145 0.071 Uiso 1 1 calc R . .
F3 F -0.2192(3) 0.35741(11) 0.2279(3) 0.1114(8) Uani 1 1 d . . .
C8 C -0.1899(3) 0.55497(15) 0.3043(3) 0.0659(7) Uani 1 1 d . . .
C1 C -0.2754(4) 0.39265(17) 0.0885(4) 0.0789(9) Uani 1 1 d . . .
C2 C -0.4560(4) 0.58645(16) -0.4125(4) 0.0785(8) Uani 1 1 d . . .
H2A H -0.5433 0.5689 -0.3920 0.094 Uiso 1 1 calc R . .
H2B H -0.3721 0.5541 -0.3880 0.094 Uiso 1 1 calc R . .
C12 C 0.0233(4) 0.63775(15) 0.3536(4) 0.0758(8) Uani 1 1 d D . .
H12A H 0.1370 0.6400 0.3729 0.091 Uiso 1 1 calc R A 1
H12B H 0.0219 0.6489 0.4582 0.091 Uiso 1 1 calc R A 1
C4 C -0.4918(6) 0.6961(2) -0.4111(7) 0.1195(15) Uani 1 1 d . . .
H4A H -0.4352 0.7366 -0.3771 0.143 Uiso 1 1 calc R . .
H4B H -0.5935 0.6980 -0.4018 0.143 Uiso 1 1 calc R . .
C5 C -0.5268(4) 0.67881(15) -0.5890(5) 0.0824(9) Uani 1 1 d . . .
H5A H -0.6343 0.6948 -0.6714 0.099 Uiso 1 1 calc R . .
H5B H -0.4424 0.6961 -0.6145 0.099 Uiso 1 1 calc R . .
C3 C -0.3831(5) 0.6431(2) -0.3069(5) 0.1142(14) Uani 1 1 d . . .
H3A H -0.2696 0.6494 -0.2851 0.137 Uiso 1 1 calc R . .
H3B H -0.3853 0.6396 -0.1997 0.137 Uiso 1 1 calc R . .
C13 C -0.0854(16) 0.6855(7) 0.2121(18) 0.124(3) Uani 0.50 1 d PDU B 1
H13A H -0.1219 0.6640 0.1046 0.148 Uiso 0.50 1 calc PR B 1
H13B H -0.1837 0.6938 0.2245 0.148 Uiso 0.50 1 calc PR B 1
C14 C -0.019(4) 0.7462(10) 0.199(3) 0.108(4) Uani 0.30 1 d PDU B 1
H14A H -0.1028 0.7700 0.1073 0.163 Uiso 0.30 1 calc PR B 1
H14B H 0.0742 0.7398 0.1783 0.163 Uiso 0.30 1 calc PR B 1
H14C H 0.0162 0.7693 0.3028 0.163 Uiso 0.30 1 calc PR B 1
C14A C -0.016(4) 0.7464(9) 0.253(3) 0.108(4) Uani 0.30 1 d PDU B 2
H14D H -0.0717 0.7735 0.1566 0.163 Uiso 0.30 1 calc PR B 2
H14E H 0.0986 0.7588 0.3152 0.163 Uiso 0.30 1 calc PR B 2
H14F H -0.0672 0.7500 0.3251 0.163 Uiso 0.30 1 calc PR B 2
C13A C -0.0255(16) 0.6810(7) 0.1976(17) 0.124(3) Uani 0.50 1 d PDU B 2
H13C H 0.0495 0.6743 0.1500 0.148 Uiso 0.50 1 calc PR B 2
H13D H -0.1373 0.6714 0.1114 0.148 Uiso 0.50 1 calc PR B 2
C14B C -0.174(2) 0.7123(10) 0.132(3) 0.102(5) Uani 0.20 1 d PDU C 3
H14G H -0.1894 0.7365 0.0346 0.153 Uiso 0.20 1 d PR C 3
H14H H -0.2623 0.6823 0.1003 0.153 Uiso 0.20 1 d PR C 3
H14I H -0.1724 0.7404 0.2172 0.153 Uiso 0.20 1 d PR C 3
C14C C -0.070(3) 0.7071(13) 0.076(3) 0.125(7) Uani 0.20 1 d PDU D 4
H14J H -0.1573 0.7362 0.0104 0.188 Uiso 0.20 1 d PR D 4
H14K H -0.0735 0.6716 0.0069 0.188 Uiso 0.20 1 d PR D 4
H14L H 0.0353 0.7283 0.1165 0.188 Uiso 0.20 1 d PR D 4
H1N H -0.626(5) 0.5876(15) -0.652(4) 0.089(10) Uiso 1 1 d . . .
H2N H -0.445(4) 0.5934(15) -0.638(4) 0.092(10) Uiso 1 1 d . . .
H1 H -0.239(5) 0.4835(16) -0.094(5) 0.101(11) Uiso 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
O2 C6 1.280(2) . ?
C6 C7 1.390(3) . ?
C6 C11 1.505(4) . ?
O1 C10 1.411(3) . ?
O1 H1 0.89(4) . ?
C7 C8 1.415(3) . ?
C7 C12 1.483(4) . ?
O3 C8 1.256(3) . ?
F1 C1 1.346(4) . ?
N1 C2 1.482(4) . ?
N1 C5 1.483(4) . ?
N1 H1N 0.94(4) . ?
N1 H2N 1.04(3) . ?
F2 C1 1.334(3) . ?
C10 C1 1.499(4) . ?
C10 C9 1.522(4) . ?
C10 C11 1.530(3) . ?
C9 C8 1.491(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
F3 C1 1.330(4) . ?
C2 C3 1.474(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C12 C13A 1.546(12) . ?
C12 C13 1.556(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C4 C3 1.494(6) . ?
C4 C5 1.513(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C13 C14 1.444(17) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14A C13A 1.452(16) . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 0.9600 . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C14B H14G 0.9600 . ?
C14B H14H 0.9600 . ?
C14B H14I 0.9600 . ?
C14C H14J 0.9599 . ?
C14C H14K 0.9601 . ?
C14C H14L 0.9599 . ?

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 C6 C7 123.2(2) . . ?
O2 C6 C11 115.8(2) . . ?
C7 C6 C11 121.04(19) . . ?
C10 O1 H1 108(3) . . ?
C6 C7 C8 120.0(2) . . ?
C6 C7 C12 121.2(2) . . ?
C8 C7 C12 118.8(2) . . ?
C2 N1 C5 107.8(2) . . ?
C2 N1 H1N 107(2) . . ?
C5 N1 H1N 117.1(19) . . ?
C2 N1 H2N 108.6(19) . . ?
C5 N1 H2N 108.8(17) . . ?
H1N N1 H2N 108(3) . . ?
O1 C10 C1 107.5(2) . . ?
O1 C10 C9 107.8(2) . . ?
C1 C10 C9 109.8(2) . . ?
O1 C10 C11 111.54(19) . . ?
C1 C10 C11 111.1(2) . . ?
C9 C10 C11 108.9(2) . . ?
C8 C9 C10 114.4(2) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C6 C11 C10 112.8(2) . . ?
C6 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C6 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O3 C8 C7 121.7(3) . . ?
O3 C8 C9 117.3(2) . . ?
C7 C8 C9 120.9(2) . . ?
F3 C1 F2 105.2(2) . . ?
F3 C1 F1 105.8(3) . . ?
F2 C1 F1 105.7(3) . . ?
F3 C1 C10 113.8(2) . . ?
F2 C1 C10 113.0(3) . . ?
F1 C1 C10 112.5(2) . . ?
C3 C2 N1 105.7(3) . . ?
C3 C2 H2A 110.6 . . ?
N1 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
N1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C7 C12 C13A 111.8(6) . . ?
C7 C12 C13 110.3(7) . . ?
C13A C12 C13 23.2(6) . . ?
C7 C12 H12A 109.6 . . ?
C13A C12 H12A 88.0 . . ?
C13 C12 H12A 109.6 . . ?
C7 C12 H12B 109.6 . . ?
C13A C12 H12B 126.7 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C3 C4 C5 103.2(3) . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
C5 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 C4 104.5(3) . . ?
N1 C5 H5A 110.8 . . ?
C4 C5 H5A 110.8 . . ?
N1 C5 H5B 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C2 C3 C4 103.7(3) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C14 C13 C12 120.4(15) . . ?
C14 C13 H13A 107.2 . . ?
C12 C13 H13A 107.2 . . ?
C14 C13 H13B 107.2 . . ?
C12 C13 H13B 107.2 . . ?
H13A C13 H13B 106.9 . . ?
C14 C13 H14H 111.1 . . ?
C12 C13 H14H 127.7 . . ?
H13A C13 H14H 62.6 . . ?
H13B C13 H14H 45.2 . . ?
C14 C13 H14I 62.8 . . ?
C12 C13 H14I 131.0 . . ?
H13A C13 H14I 118.4 . . ?
H13B C13 H14I 44.5 . . ?
H14H C13 H14I 66.4 . . ?
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 C14 H14G 72.0 . . ?
H14A C14 H14G 39.3 . . ?
H14B C14 H14G 112.3 . . ?
H14C C14 H14G 134.7 . . ?
C13 C14 H14I 57.7 . . ?
H14A C14 H14I 73.8 . . ?
H14B C14 H14I 166.4 . . ?
H14C C14 H14I 80.9 . . ?
H14G C14 H14I 61.4 . . ?
C13 C14 H14J 79.1 . . ?
H14A C14 H14J 40.3 . . ?
H14B C14 H14J 96.5 . . ?
H14C C14 H14J 147.0 . . ?
H14G C14 H14J 16.0 . . ?
H14I C14 H14J 77.4 . . ?
C13 C14 H14L 94.9 . . ?
H14A C14 H14L 92.0 . . ?
H14B C14 H14L 29.4 . . ?
H14C C14 H14L 138.8 . . ?
H14G C14 H14L 83.7 . . ?
H14I C14 H14L 140.0 . . ?
H14J C14 H14L 68.5 . . ?
C13A C14A H14D 109.5 . . ?
C13A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
C13A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C13A C14A H14I 86.5 . . ?
H14D C14A H14I 77.1 . . ?
H14E C14A H14I 158.4 . . ?
H14F C14A H14I 49.9 . . ?
C13A C14A H14L 59.2 . . ?
H14D C14A H14L 70.4 . . ?
H14E C14A H14L 82.9 . . ?
H14F C14A H14L 166.3 . . ?
H14I C14A H14L 118.5 . . ?
C14A C13A C12 107.7(13) . . ?
C14A C13A H13C 110.2 . . ?
C12 C13A H13C 110.2 . . ?
C14A C13A H13D 110.2 . . ?
C12 C13A H13D 110.2 . . ?
H13C C13A H13D 108.5 . . ?
C14A C13A H14K 115.8 . . ?
C12 C13A H14K 136.5 . . ?
H13C C13A H14K 53.0 . . ?
H13D C13A H14K 56.8 . . ?
C14A C13A H14L 63.5 . . ?
C12 C13A H14L 145.1 . . ?
H13C C13A H14L 51.8 . . ?
H13D C13A H14L 104.3 . . ?
H14K C13A H14L 61.9 . . ?
H14G C14B H14H 109.5 . . ?
H14G C14B H14I 109.5 . . ?
H14H C14B H14I 109.5 . . ?
H14G C14B H14J 16.2 . . ?
H14H C14B H14J 115.4 . . ?
H14I C14B H14J 118.3 . . ?
H14G C14C H14J 21.4 . . ?
H14G C14C H14K 117.7 . . ?
H14J C14C H14K 109.5 . . ?
H14G C14C H14L 119.9 . . ?
H14J C14C H14L 109.5 . . ?
H14K C14C H14L 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
O2 C6 C7 C8 -177.8(2) . . . . ?
C11 C6 C7 C8 0.4(3) . . . . ?
O2 C6 C7 C12 3.8(4) . . . . ?
C11 C6 C7 C12 -177.9(2) . . . . ?
O1 C10 C9 C8 -72.8(3) . . . . ?
C1 C10 C9 C8 170.3(2) . . . . ?
C11 C10 C9 C8 48.4(3) . . . . ?
O2 C6 C11 C10 -153.3(2) . . . . ?
C7 C6 C11 C10 28.3(3) . . . . ?
O1 C10 C11 C6 67.9(3) . . . . ?
C1 C10 C11 C6 -172.2(2) . . . . ?
C9 C10 C11 C6 -51.0(3) . . . . ?
C6 C7 C8 O3 174.3(2) . . . . ?
C12 C7 C8 O3 -7.3(4) . . . . ?
C6 C7 C8 C9 -3.8(4) . . . . ?
C12 C7 C8 C9 174.6(2) . . . . ?
C10 C9 C8 O3 159.6(2) . . . . ?
C10 C9 C8 C7 -22.2(4) . . . . ?
O1 C10 C1 F3 -176.0(2) . . . . ?
C9 C10 C1 F3 -58.9(3) . . . . ?
C11 C10 C1 F3 61.7(3) . . . . ?
O1 C10 C1 F2 -56.0(3) . . . . ?
C9 C10 C1 F2 61.1(3) . . . . ?
C11 C10 C1 F2 -178.3(2) . . . . ?
O1 C10 C1 F1 63.7(3) . . . . ?
C9 C10 C1 F1 -179.3(2) . . . . ?
C11 C10 C1 F1 -58.6(3) . . . . ?
C5 N1 C2 C3 -13.2(3) . . . . ?
C6 C7 C12 C13A 81.1(5) . . . . ?
C8 C7 C12 C13A -97.3(5) . . . . ?
C6 C7 C12 C13 105.9(5) . . . . ?
C8 C7 C12 C13 -72.4(6) . . . . ?
C2 N1 C5 C4 -11.2(3) . . . . ?
C3 C4 C5 N1 30.9(4) . . . . ?
N1 C2 C3 C4 32.6(4) . . . . ?
C5 C4 C3 C2 -39.3(4) . . . . ?
C7 C12 C13 C14 -157.2(13) . . . . ?
C13A C12 C13 C14 -59(3) . . . . ?
C7 C12 C13A C14A 158.9(13) . . . . ?
C13 C12 C13A C14A 68(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.864
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044

