# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1572250'
_audit_update_record             
;
2017-09-02 deposited with the CCDC.
2017-10-02 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C13 H12 F3 N O2'

_chemical_formula_weight         271.24



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                   8.3643(6)

_cell_length_b                   11.0918(9)

_cell_length_c                   14.0147(11)

_cell_angle_alpha                90.00

_cell_angle_beta                 107.36

_cell_angle_gamma                90.00

_cell_volume                     1240.98(17)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    1203

_cell_measurement_theta_min      3.56

_cell_measurement_theta_max      25.49



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.45

_exptl_crystal_size_mid          0.32

_exptl_crystal_size_min          0.25

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.452

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             560

_exptl_absorpt_coefficient_mu    0.128

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9448

_exptl_absorpt_correction_T_max  0.9688

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      293(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  'multiwire proportional'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            3439

_diffrn_reflns_av_R_equivalents  0.0977

_diffrn_reflns_av_sigmaI/netI    0.1073

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -13

_diffrn_reflns_limit_k_max       8

_diffrn_reflns_limit_l_min       -11

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_theta_min         3.56

_diffrn_reflns_theta_max         25.49

_reflns_number_total             2044

_reflns_number_gt                1172

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker FRAMBO'

_computing_cell_refinement       'Bruker FRAMBO'

_computing_data_reduction        'Bruker SAINT'

_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)+(0.1335P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         2044

_refine_ls_number_parameters     174

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1219

_refine_ls_R_factor_gt           0.0967

_refine_ls_wR_factor_ref         0.2635

_refine_ls_wR_factor_gt          0.2413

_refine_ls_goodness_of_fit_ref   0.982

_refine_ls_restrained_S_all      0.982

_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































F1 F 0.9992(4) 0.0115(2) 0.1145(2) 0.0952(10) Uani 1 1 d . . .
F2 F 0.9902(5) 0.3248(3) 0.4719(2) 0.1220(13) Uani 1 1 d . . .
F3 F 1.1351(4) 0.4184(3) 0.3903(2) 0.1086(11) Uani 1 1 d . . .
N1 N 1.0443(4) 0.5799(2) 0.1655(2) 0.0489(8) Uani 1 1 d . . .
O1 O 0.8660(4) 0.6190(2) 0.2524(3) 0.0907(13) Uani 1 1 d . . .
O2 O 1.2513(4) 0.5404(3) 0.0978(3) 0.0806(10) Uani 1 1 d . . .
C1 C 1.1384(5) 0.5002(3) 0.1275(3) 0.0526(10) Uani 1 1 d . . .
C2 C 1.0983(4) 0.3723(3) 0.1258(2) 0.0460(9) Uani 1 1 d . . .
C3 C 0.9699(5) 0.3290(3) 0.1606(3) 0.0503(10) Uani 1 1 d . . .
C4 C 0.8662(5) 0.4143(3) 0.2031(3) 0.0533(10) Uani 1 1 d . . .
C5 C 0.9276(5) 0.5444(3) 0.2114(3) 0.0592(11) Uani 1 1 d . . .
C6 C 1.1906(5) 0.2915(4) 0.0860(3) 0.0551(10) Uani 1 1 d . . .
H6 H 1.2751 0.3207 0.0617 0.066 Uiso 1 1 calc R . .
C7 C 1.1585(5) 0.1706(4) 0.0822(3) 0.0623(11) Uani 1 1 d . . .
H7 H 1.2212 0.1173 0.0567 0.075 Uiso 1 1 calc R . .
C8 C 1.0312(5) 0.1299(3) 0.1170(3) 0.0621(11) Uani 1 1 d . . .
C9 C 0.9355(5) 0.2065(3) 0.1557(3) 0.0651(12) Uani 1 1 d . . .
H9 H 0.8494 0.1762 0.1782 0.078 Uiso 1 1 calc R . .
C10 C 0.6843(5) 0.4186(4) 0.1300(3) 0.0754(14) Uani 1 1 d . . .
H10A H 0.6168 0.4709 0.1567 0.113 Uiso 1 1 calc R . .
H10B H 0.6372 0.3389 0.1221 0.113 Uiso 1 1 calc R . .
H10C H 0.6869 0.4486 0.0662 0.113 Uiso 1 1 calc R . .
C11 C 0.8539(5) 0.3739(3) 0.3052(3) 0.0591(11) Uani 1 1 d . . .
H11A H 0.8058 0.4394 0.3334 0.071 Uiso 1 1 calc R . .
H11B H 0.7765 0.3066 0.2948 0.071 Uiso 1 1 calc R . .
C12 C 1.0144(6) 0.3368(5) 0.3806(3) 0.0756(13) Uani 1 1 d . . .
H12 H 1.0512 0.2594 0.3606 0.091 Uiso 1 1 calc R . .
C13 C 1.0818(6) 0.7096(3) 0.1636(3) 0.0654(11) Uani 1 1 d . . .
H13A H 1.1777 0.7289 0.2191 0.098 Uiso 1 1 calc R . .
H13B H 0.9872 0.7557 0.1682 0.098 Uiso 1 1 calc R . .
H13C H 1.1050 0.7288 0.1023 0.098 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 C8 1.338(4) . ?
F2 C12 1.360(4) . ?
F3 C12 1.333(5) . ?
N1 C5 1.377(4) . ?
N1 C1 1.391(4) . ?
N1 C13 1.475(4) . ?
O1 C5 1.207(4) . ?
O2 C1 1.224(4) . ?
C1 C2 1.456(5) . ?
C2 C3 1.391(4) . ?
C2 C6 1.403(5) . ?
C3 C9 1.386(5) . ?
C3 C4 1.521(4) . ?
C4 C5 1.524(5) . ?
C4 C11 1.531(5) . ?
C4 C10 1.561(6) . ?
C6 C7 1.365(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(5) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.497(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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

























































C5 N1 C1 124.0(3) . . ?
C5 N1 C13 118.2(3) . . ?
C1 N1 C13 117.7(3) . . ?
O2 C1 N1 118.8(3) . . ?
O2 C1 C2 123.1(3) . . ?
N1 C1 C2 118.1(3) . . ?
C3 C2 C6 119.5(3) . . ?
C3 C2 C1 121.9(3) . . ?
C6 C2 C1 118.6(3) . . ?
C9 C3 C2 119.5(3) . . ?
C9 C3 C4 119.6(3) . . ?
C2 C3 C4 120.8(3) . . ?
C3 C4 C5 113.6(3) . . ?
C3 C4 C11 112.9(3) . . ?
C5 C4 C11 108.7(3) . . ?
C3 C4 C10 108.7(3) . . ?
C5 C4 C10 105.2(3) . . ?
C11 C4 C10 107.4(3) . . ?
O1 C5 N1 119.3(3) . . ?
O1 C5 C4 120.2(3) . . ?
N1 C5 C4 120.3(3) . . ?
C7 C6 C2 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C2 C6 H6 119.4 . . ?
C6 C7 C8 118.3(3) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
F1 C8 C7 119.0(3) . . ?
F1 C8 C9 118.5(3) . . ?
C7 C8 C9 122.5(4) . . ?
C8 C9 C3 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C3 C9 H9 120.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C4 116.4(3) . . ?
C12 C11 H11A 108.2 . . ?
C4 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C4 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
F3 C12 F2 106.9(4) . . ?
F3 C12 C11 112.2(4) . . ?
F2 C12 C11 109.7(3) . . ?
F3 C12 H12 109.3 . . ?
F2 C12 H12 109.3 . . ?
C11 C12 H12 109.3 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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










































C5 N1 C1 O2 -172.3(4) . . . . ?
C13 N1 C1 O2 2.6(6) . . . . ?
C5 N1 C1 C2 7.2(5) . . . . ?
C13 N1 C1 C2 -177.8(3) . . . . ?
O2 C1 C2 C3 179.6(4) . . . . ?
N1 C1 C2 C3 0.1(5) . . . . ?
O2 C1 C2 C6 -1.6(6) . . . . ?
N1 C1 C2 C6 178.9(3) . . . . ?
C6 C2 C3 C9 0.3(6) . . . . ?
C1 C2 C3 C9 179.0(3) . . . . ?
C6 C2 C3 C4 -179.3(3) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C9 C3 C4 C5 175.3(4) . . . . ?
C2 C3 C4 C5 -5.1(6) . . . . ?
C9 C3 C4 C11 51.0(5) . . . . ?
C2 C3 C4 C11 -129.5(4) . . . . ?
C9 C3 C4 C10 -68.0(5) . . . . ?
C2 C3 C4 C10 111.5(4) . . . . ?
C1 N1 C5 O1 171.4(4) . . . . ?
C13 N1 C5 O1 -3.5(6) . . . . ?
C1 N1 C5 C4 -13.6(6) . . . . ?
C13 N1 C5 C4 171.5(4) . . . . ?
C3 C4 C5 O1 -173.2(4) . . . . ?
C11 C4 C5 O1 -46.6(5) . . . . ?
C10 C4 C5 O1 68.2(5) . . . . ?
C3 C4 C5 N1 11.9(6) . . . . ?
C11 C4 C5 N1 138.5(4) . . . . ?
C10 C4 C5 N1 -106.8(4) . . . . ?
C3 C2 C6 C7 -1.1(6) . . . . ?
C1 C2 C6 C7 -179.9(3) . . . . ?
C2 C6 C7 C8 1.0(6) . . . . ?
C6 C7 C8 F1 -179.4(3) . . . . ?
C6 C7 C8 C9 -0.2(7) . . . . ?
F1 C8 C9 C3 178.7(4) . . . . ?
C7 C8 C9 C3 -0.6(7) . . . . ?
C2 C3 C9 C8 0.6(6) . . . . ?
C4 C3 C9 C8 -179.9(4) . . . . ?
C3 C4 C11 C12 46.9(5) . . . . ?
C5 C4 C11 C12 -80.1(4) . . . . ?
C10 C4 C11 C12 166.7(4) . . . . ?
C4 C11 C12 F3 50.2(5) . . . . ?
C4 C11 C12 F2 168.9(3) . . . . ?



_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        25.49

_diffrn_measured_fraction_theta_full 0.887

_refine_diff_density_max         0.301

_refine_diff_density_min         -0.355

_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 1572251'
_audit_update_record             
;
2017-09-02 deposited with the CCDC.
2017-10-02 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C14 H15 F2 N O3'

_chemical_formula_weight         283.27



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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P21/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                   7.9457(7)

_cell_length_b                   19.7796(15)

_cell_length_c                   8.9411(8)

_cell_angle_alpha                90.00

_cell_angle_beta                 107.130(9)

_cell_angle_gamma                90.00

_cell_volume                     1342.9(2)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    1402

_cell_measurement_theta_min      3.38

_cell_measurement_theta_max      25.50



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.54

_exptl_crystal_size_mid          0.40

_exptl_crystal_size_min          0.32

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.401

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             592

_exptl_absorpt_coefficient_mu    0.116

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9399

_exptl_absorpt_correction_T_max  0.9637

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      293(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  'multiwire proportional'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            7298

_diffrn_reflns_av_R_equivalents  0.0235

_diffrn_reflns_av_sigmaI/netI    0.0297

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -23

_diffrn_reflns_limit_k_max       17

_diffrn_reflns_limit_l_min       -8

_diffrn_reflns_limit_l_max       10

_diffrn_reflns_theta_min         3.38

_diffrn_reflns_theta_max         25.50

_reflns_number_total             2461

_reflns_number_gt                1883

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker FRAMBO'

_computing_cell_refinement       'Bruker FRAMBO'

_computing_data_reduction        'Bruker SAINT'

_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)+(0.0568P)²+0.8805P] 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         2461

_refine_ls_number_parameters     184

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0794

_refine_ls_R_factor_gt           0.0613

_refine_ls_wR_factor_ref         0.1553

_refine_ls_wR_factor_gt          0.1443

_refine_ls_goodness_of_fit_ref   1.074

_refine_ls_restrained_S_all      1.074

_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



































C1 C 0.6139(3) 0.15539(13) 0.3623(3) 0.0440(6) Uani 1 1 d . . .
C2 C 0.4456(3) 0.13268(12) 0.2551(3) 0.0404(6) Uani 1 1 d . . .
C3 C 0.2894(3) 0.13679(12) 0.2931(3) 0.0376(6) Uani 1 1 d . . .
C4 C 0.2867(3) 0.16342(12) 0.4519(3) 0.0378(6) Uani 1 1 d . . .
C5 C 0.4684(4) 0.17935(14) 0.5633(3) 0.0469(7) Uani 1 1 d . . .
C6 C 0.4439(4) 0.10840(14) 0.1074(3) 0.0511(7) Uani 1 1 d . . .
H6 H 0.5488 0.1053 0.0816 0.061 Uiso 1 1 calc R . .
C7 C 0.2901(4) 0.08923(15) 0.0011(3) 0.0544(7) Uani 1 1 d . . .
H7 H 0.2906 0.0725 -0.0959 0.065 Uiso 1 1 calc R . .
C8 C 0.1332(4) 0.09470(14) 0.0378(3) 0.0474(7) Uani 1 1 d . . .
C9 C 0.1321(3) 0.11790(13) 0.1833(3) 0.0414(6) Uani 1 1 d . . .
H9 H 0.0265 0.1209 0.2079 0.050 Uiso 1 1 calc R . .
C10 C 0.1859(4) 0.23091(13) 0.4294(3) 0.0514(7) Uani 1 1 d . . .
H10A H 0.2439 0.2631 0.3811 0.077 Uiso 1 1 calc R . .
H10B H 0.1834 0.2478 0.5294 0.077 Uiso 1 1 calc R . .
H10C H 0.0676 0.2240 0.3638 0.077 Uiso 1 1 calc R . .
C11 C 0.7822(4) 0.20270(19) 0.6145(4) 0.0714(10) Uani 1 1 d . . .
H11A H 0.7601 0.2307 0.6944 0.107 Uiso 1 1 calc R . .
H11B H 0.8438 0.2284 0.5560 0.107 Uiso 1 1 calc R . .
H11C H 0.8525 0.1646 0.6622 0.107 Uiso 1 1 calc R . .
C12 C -0.1779(4) 0.08203(19) -0.0474(4) 0.0711(9) Uani 1 1 d . . .
H12A H -0.1769 0.0551 0.0421 0.107 Uiso 1 1 calc R . .
H12B H -0.2697 0.0665 -0.1367 0.107 Uiso 1 1 calc R . .
H12C H -0.1986 0.1285 -0.0271 0.107 Uiso 1 1 calc R . .
C13 C 0.1943(3) 0.11268(13) 0.5329(3) 0.0437(6) Uani 1 1 d . . .
H13A H 0.2042 0.1292 0.6373 0.052 Uiso 1 1 calc R . .
H13B H 0.0701 0.1114 0.4753 0.052 Uiso 1 1 calc R . .
C14 C 0.2656(4) 0.04214(15) 0.5456(3) 0.0596(8) Uani 1 1 d . . .
H14 H 0.2470 0.0226 0.4413 0.071 Uiso 1 1 calc R . .
F1 F 0.1844(3) 0.00399(10) 0.6299(2) 0.0971(8) Uani 1 1 d . . .
F2 F 0.4391(3) 0.04120(11) 0.6265(3) 0.0945(7) Uani 1 1 d . . .
N1 N 0.6134(3) 0.17875(11) 0.5085(3) 0.0480(6) Uani 1 1 d . . .
O1 O 0.7515(2) 0.15414(11) 0.3274(2) 0.0610(6) Uani 1 1 d . . .
O2 O 0.4831(3) 0.19571(12) 0.6974(2) 0.0681(7) Uani 1 1 d . . .
O3 O -0.0133(3) 0.07620(12) -0.0778(2) 0.0651(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




































C1 O1 1.222(3) . ?
C1 N1 1.388(3) . ?
C1 C2 1.467(4) . ?
C2 C3 1.383(3) . ?
C2 C6 1.402(4) . ?
C3 C9 1.394(3) . ?
C3 C4 1.520(3) . ?
C4 C5 1.526(4) . ?
C4 C10 1.539(3) . ?
C4 C13 1.544(3) . ?
C5 O2 1.214(3) . ?
C5 N1 1.378(3) . ?
C6 C7 1.362(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(4) . ?
C7 H7 0.9300 . ?
C8 O3 1.359(3) . ?
C8 C9 1.382(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N1 1.474(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O3 1.417(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.498(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 F2 1.355(4) . ?
C14 F1 1.356(4) . ?
C14 H14 0.9800 . ?



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
































































O1 C1 N1 119.9(2) . . ?
O1 C1 C2 122.6(2) . . ?
N1 C1 C2 117.5(2) . . ?
C3 C2 C6 119.4(2) . . ?
C3 C2 C1 122.2(2) . . ?
C6 C2 C1 118.3(2) . . ?
C2 C3 C9 119.7(2) . . ?
C2 C3 C4 120.7(2) . . ?
C9 C3 C4 119.6(2) . . ?
C3 C4 C5 114.2(2) . . ?
C3 C4 C10 109.2(2) . . ?
C5 C4 C10 105.2(2) . . ?
C3 C4 C13 110.6(2) . . ?
C5 C4 C13 108.5(2) . . ?
C10 C4 C13 108.9(2) . . ?
O2 C5 N1 120.4(2) . . ?
O2 C5 C4 119.8(2) . . ?
N1 C5 C4 119.7(2) . . ?
C7 C6 C2 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C2 C6 H6 119.7 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
O3 C8 C9 124.3(3) . . ?
O3 C8 C7 115.4(2) . . ?
C9 C8 C7 120.3(2) . . ?
C8 C9 C3 119.9(2) . . ?
C8 C9 H9 120.0 . . ?
C3 C9 H9 120.0 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 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 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C4 114.8(2) . . ?
C14 C13 H13A 108.6 . . ?
C4 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C4 C13 H13B 108.6 . . ?
H13A C13 H13B 107.5 . . ?
F2 C14 F1 105.7(2) . . ?
F2 C14 C13 110.9(2) . . ?
F1 C14 C13 109.2(3) . . ?
F2 C14 H14 110.3 . . ?
F1 C14 H14 110.3 . . ?
C13 C14 H14 110.3 . . ?
C5 N1 C1 124.9(2) . . ?
C5 N1 C11 117.8(2) . . ?
C1 N1 C11 117.3(2) . . ?
C8 O3 C12 117.7(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












































O1 C1 C2 C3 -177.4(2) . . . . ?
N1 C1 C2 C3 2.9(4) . . . . ?
O1 C1 C2 C6 0.3(4) . . . . ?
N1 C1 C2 C6 -179.5(2) . . . . ?
C6 C2 C3 C9 -1.1(4) . . . . ?
C1 C2 C3 C9 176.5(2) . . . . ?
C6 C2 C3 C4 -179.5(2) . . . . ?
C1 C2 C3 C4 -1.9(4) . . . . ?
C2 C3 C4 C5 -4.1(3) . . . . ?
C9 C3 C4 C5 177.5(2) . . . . ?
C2 C3 C4 C10 113.3(3) . . . . ?
C9 C3 C4 C10 -65.1(3) . . . . ?
C2 C3 C4 C13 -126.8(2) . . . . ?
C9 C3 C4 C13 54.8(3) . . . . ?
C3 C4 C5 O2 -174.1(2) . . . . ?
C10 C4 C5 O2 66.2(3) . . . . ?
C13 C4 C5 O2 -50.2(3) . . . . ?
C3 C4 C5 N1 9.6(3) . . . . ?
C10 C4 C5 N1 -110.1(3) . . . . ?
C13 C4 C5 N1 133.5(2) . . . . ?
C3 C2 C6 C7 0.3(4) . . . . ?
C1 C2 C6 C7 -177.4(3) . . . . ?
C2 C6 C7 C8 1.1(4) . . . . ?
C6 C7 C8 O3 178.1(3) . . . . ?
C6 C7 C8 C9 -1.7(4) . . . . ?
O3 C8 C9 C3 -178.9(2) . . . . ?
C7 C8 C9 C3 0.9(4) . . . . ?
C2 C3 C9 C8 0.5(4) . . . . ?
C4 C3 C9 C8 178.9(2) . . . . ?
C3 C4 C13 C14 53.2(3) . . . . ?
C5 C4 C13 C14 -72.8(3) . . . . ?
C10 C4 C13 C14 173.2(2) . . . . ?
C4 C13 C14 F2 58.8(3) . . . . ?
C4 C13 C14 F1 174.9(2) . . . . ?
O2 C5 N1 C1 174.1(3) . . . . ?
C4 C5 N1 C1 -9.6(4) . . . . ?
O2 C5 N1 C11 -3.9(4) . . . . ?
C4 C5 N1 C11 172.4(3) . . . . ?
O1 C1 N1 C5 -176.6(3) . . . . ?
C2 C1 N1 C5 3.1(4) . . . . ?
O1 C1 N1 C11 1.4(4) . . . . ?
C2 C1 N1 C11 -178.9(2) . . . . ?
C9 C8 O3 C12 0.9(4) . . . . ?
C7 C8 O3 C12 -178.8(3) . . . . ?



_diffrn_measured_fraction_theta_max 0.982

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.982

_refine_diff_density_max         0.339

_refine_diff_density_min         -0.244

_refine_diff_density_rms         0.042

