# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_20150722_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nfk4s
_database_code_depnum_ccdc_archive 'CCDC 1532365'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2018-02-12 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)/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                   7.8606(2)
_cell_length_b                   8.5158(2)
_cell_length_c                   18.6068(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.7710(10)
_cell_angle_gamma                90.00
_cell_volume                     1230.96(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    8006
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.22

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9314
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(1)
_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            19921
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3068
_reflns_number_gt                2366
_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)+(0.0516P)²+0.2559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3068
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
F1A F 0.2379(15) 0.5183(5) 0.5251(3) 0.132(2) Uani 0.453(10) 1 d P A 1
F2A F 0.4023(9) 0.4050(13) 0.6027(5) 0.163(4) Uani 0.453(10) 1 d P A 1
F3A F 0.2195(9) 0.3483(7) 0.63852(19) 0.102(2) Uani 0.453(10) 1 d P A 1
F1B F 0.1478(9) 0.5054(6) 0.5517(4) 0.122(2) Uani 0.547(10) 1 d P A 2
F2B F 0.4043(6) 0.4442(7) 0.5843(4) 0.116(2) Uani 0.547(10) 1 d P A 2
F3B F 0.1489(11) 0.4040(10) 0.6142(6) 0.172(4) Uani 0.547(10) 1 d P A 2
O1 O 0.85117(12) 0.00525(13) 0.25064(6) 0.0630(3) Uani 1 1 d . . .
O2 O 0.08770(13) 0.17107(12) 0.52217(6) 0.0629(3) Uani 1 1 d . . .
N1 N 0.21195(14) -0.00898(13) 0.42195(6) 0.0515(3) Uani 1 1 d . . .
H1A H 0.1303 0.0066 0.4471 0.062 Uiso 1 1 calc R . .
C1 C 0.34280(16) 0.09080(14) 0.42931(6) 0.0433(3) Uani 1 1 d . . .
C2 C 0.2000(2) -0.14369(18) 0.37327(9) 0.0618(4) Uani 1 1 d . . .
H2A H 0.0814 -0.1788 0.3627 0.074 Uiso 1 1 calc R . .
H2B H 0.2690 -0.2294 0.3964 0.074 Uiso 1 1 calc R . .
C3 C 0.26326(18) -0.0985(2) 0.30379(8) 0.0612(4) Uani 1 1 d . . .
H3A H 0.2678 -0.1909 0.2736 0.073 Uiso 1 1 calc R . .
H3B H 0.1842 -0.0240 0.2771 0.073 Uiso 1 1 calc R . .
C4 C 0.56176(17) -0.04890(16) 0.27523(7) 0.0501(3) Uani 1 1 d . . .
H4A H 0.5357 -0.1100 0.2336 0.060 Uiso 1 1 calc R . .
C5 C 0.72261(16) 0.01947(16) 0.29180(7) 0.0478(3) Uani 1 1 d . . .
C6 C 0.76127(17) 0.11120(16) 0.35385(7) 0.0506(3) Uani 1 1 d . . .
H6A H 0.8693 0.1573 0.3650 0.061 Uiso 1 1 calc R . .
C7 C 0.64027(17) 0.13392(15) 0.39872(7) 0.0471(3) Uani 1 1 d . . .
H7A H 0.6675 0.1952 0.4403 0.057 Uiso 1 1 calc R . .
C8 C 0.47683(15) 0.06650(14) 0.38301(6) 0.0420(3) Uani 1 1 d . . .
C9 C 0.43933(16) -0.02654(15) 0.32051(7) 0.0463(3) Uani 1 1 d . . .
C10 C 0.35034(17) 0.21684(15) 0.47810(7) 0.0483(3) Uani 1 1 d . . .
H10A H 0.4448 0.2839 0.4823 0.058 Uiso 1 1 calc R . .
C11 C 0.22237(18) 0.24590(15) 0.52051(7) 0.0494(3) Uani 1 1 d . A .
C12 C 0.2487(2) 0.39026(19) 0.57053(10) 0.0669(4) Uani 1 1 d . . .
C13 C 0.8209(2) -0.0921(2) 0.18789(10) 0.0786(5) Uani 1 1 d . . .
H13A H 0.9211 -0.0926 0.1642 0.118 Uiso 1 1 calc R . .
H13B H 0.7243 -0.0523 0.1551 0.118 Uiso 1 1 calc R . .
H13C H 0.7967 -0.1972 0.2021 0.118 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
F1A C12 1.374(5) . ?
F2A C12 1.270(6) . ?
F3A C12 1.367(4) . ?
F1B C12 1.277(4) . ?
F2B C12 1.295(4) . ?
F3B C12 1.218(4) . ?
O1 C5 1.3633(15) . ?
O1 C13 1.4222(19) . ?
O2 C11 1.2400(16) . ?
N1 C1 1.3251(16) . ?
N1 C2 1.4557(17) . ?
N1 H1A 0.8600 . ?
C1 C10 1.4012(18) . ?
C1 C8 1.4738(17) . ?
C2 C3 1.504(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C9 1.5023(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.3834(18) . ?
C4 C9 1.3854(18) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3887(19) . ?
C6 C7 1.3716(18) . ?
C6 H6A 0.9300 . ?
C7 C8 1.3968(17) . ?
C7 H7A 0.9300 . ?
C8 C9 1.4009(17) . ?
C10 C11 1.3920(18) . ?
C10 H10A 0.9300 . ?
C11 C12 1.537(2) . ?
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 O1 C13 117.86(11) . . ?
C1 N1 C2 123.03(11) . . ?
C1 N1 H1A 118.5 . . ?
C2 N1 H1A 118.5 . . ?
N1 C1 C10 120.91(12) . . ?
N1 C1 C8 117.54(11) . . ?
C10 C1 C8 121.53(11) . . ?
N1 C2 C3 109.57(12) . . ?
N1 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C9 C3 C2 109.95(12) . . ?
C9 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C9 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C9 120.17(12) . . ?
C5 C4 H4A 119.9 . . ?
C9 C4 H4A 119.9 . . ?
O1 C5 C4 124.61(12) . . ?
O1 C5 C6 115.47(12) . . ?
C4 C5 C6 119.92(12) . . ?
C7 C6 C5 120.08(12) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C6 C7 C8 121.04(12) . . ?
C6 C7 H7A 119.5 . . ?
C8 C7 H7A 119.5 . . ?
C7 C8 C9 118.47(11) . . ?
C7 C8 C1 122.46(11) . . ?
C9 C8 C1 119.08(11) . . ?
C4 C9 C8 120.32(11) . . ?
C4 C9 C3 121.43(11) . . ?
C8 C9 C3 118.25(11) . . ?
C11 C10 C1 122.73(12) . . ?
C11 C10 H10A 118.6 . . ?
C1 C10 H10A 118.6 . . ?
O2 C11 C10 128.04(12) . . ?
O2 C11 C12 115.64(12) . . ?
C10 C11 C12 116.30(12) . . ?
F3B C12 F2A 109.8(8) . . ?
F3B C12 F1B 70.9(9) . . ?
F2A C12 F1B 124.1(5) . . ?
F3B C12 F2B 121.2(5) . . ?
F2A C12 F2B 21.5(7) . . ?
F1B C12 F2B 108.1(4) . . ?
F3B C12 F3A 36.1(5) . . ?
F2A C12 F3A 82.6(7) . . ?
F1B C12 F3A 105.6(6) . . ?
F2B C12 F3A 101.3(4) . . ?
F3B C12 F1A 110.4(9) . . ?
F2A C12 F1A 100.2(5) . . ?
F1B C12 F1A 40.9(2) . . ?
F2B C12 F1A 79.0(4) . . ?
F3A C12 F1A 140.6(5) . . ?
F3B C12 C11 116.1(2) . . ?
F2A C12 C11 113.3(4) . . ?
F1B C12 C11 115.3(2) . . ?
F2B C12 C11 116.1(2) . . ?
F3A C12 C11 109.0(3) . . ?
F1A C12 C11 105.8(3) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 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
C2 N1 C1 C10 -178.58(13) . . . . ?
C2 N1 C1 C8 3.00(19) . . . . ?
C1 N1 C2 C3 -39.35(19) . . . . ?
N1 C2 C3 C9 52.85(17) . . . . ?
C13 O1 C5 C4 -2.9(2) . . . . ?
C13 O1 C5 C6 177.71(14) . . . . ?
C9 C4 C5 O1 -179.63(13) . . . . ?
C9 C4 C5 C6 -0.2(2) . . . . ?
O1 C5 C6 C7 179.52(12) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C9 0.60(19) . . . . ?
C6 C7 C8 C1 -178.89(12) . . . . ?
N1 C1 C8 C7 -162.05(12) . . . . ?
C10 C1 C8 C7 19.54(19) . . . . ?
N1 C1 C8 C9 18.47(18) . . . . ?
C10 C1 C8 C9 -159.94(12) . . . . ?
C5 C4 C9 C8 0.6(2) . . . . ?
C5 C4 C9 C3 179.68(13) . . . . ?
C7 C8 C9 C4 -0.75(19) . . . . ?
C1 C8 C9 C4 178.75(12) . . . . ?
C7 C8 C9 C3 -179.89(12) . . . . ?
C1 C8 C9 C3 -0.39(18) . . . . ?
C2 C3 C9 C4 145.49(14) . . . . ?
C2 C3 C9 C8 -35.38(18) . . . . ?
N1 C1 C10 C11 -0.8(2) . . . . ?
C8 C1 C10 C11 177.57(12) . . . . ?
C1 C10 C11 O2 -0.5(2) . . . . ?
C1 C10 C11 C12 -179.18(13) . . . . ?
O2 C11 C12 F3B 10.3(8) . . . . ?
C10 C11 C12 F3B -170.9(8) . . . . ?
O2 C11 C12 F2A 138.7(7) . . . . ?
C10 C11 C12 F2A -42.4(7) . . . . ?
O2 C11 C12 F1B -69.8(6) . . . . ?
C10 C11 C12 F1B 109.0(5) . . . . ?
O2 C11 C12 F2B 162.2(4) . . . . ?
C10 C11 C12 F2B -18.9(4) . . . . ?
O2 C11 C12 F3A 48.7(4) . . . . ?
C10 C11 C12 F3A -132.4(3) . . . . ?
O2 C11 C12 F1A -112.5(5) . . . . ?
C10 C11 C12 F1A 66.4(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.86 2.42 3.0465(15) 130.3 3_556

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_20150901lt_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1nfk5t
_database_code_depnum_ccdc_archive 'CCDC 1532366'
_audit_update_record             
;
2017-02-13 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 F3 N2 O'
_chemical_formula_weight         296.29

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)/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                   6.9263(1)
_cell_length_b                   8.7238(1)
_cell_length_c                   22.5349(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.292(1)
_cell_angle_gamma                90.00
_cell_volume                     1355.84(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      30.47

_exptl_crystal_description       block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(1)
_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            2669
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2669
_reflns_number_gt                2421
_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)+(0.0373P)²+0.9104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2669
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.63850(12) 0.07315(10) 0.14735(4) 0.0246(2) Uani 1 1 d . . .
F2 F 0.79966(11) -0.00533(11) 0.22781(4) 0.0270(2) Uani 1 1 d . . .
F3 F 0.62260(13) -0.16415(10) 0.17351(4) 0.0256(2) Uani 1 1 d . . .
O1 O 0.48732(13) 0.16695(10) 0.25305(4) 0.0162(2) Uani 1 1 d . . .
H1A H 0.4881 0.2302 0.2250 0.024 Uiso 1 1 calc R . .
N1 N 0.14273(16) -0.10546(13) 0.32162(5) 0.0147(2) Uani 1 1 d . . .
N2 N 0.54039(16) 0.14868(13) 0.38021(5) 0.0155(2) Uani 1 1 d . . .
H2A H 0.6285 0.1552 0.3546 0.019 Uiso 1 1 calc R . .
C1 C 0.31243(19) -0.04294(14) 0.32543(6) 0.0134(3) Uani 1 1 d . . .
C2 C 0.00231(19) -0.04567(16) 0.36136(6) 0.0158(3) Uani 1 1 d . . .
H2B H -0.1030 -0.1218 0.3631 0.019 Uiso 1 1 calc R . .
H2C H -0.0563 0.0491 0.3435 0.019 Uiso 1 1 calc R . .
C3 C 0.08607(19) -0.00980(16) 0.42505(6) 0.0162(3) Uani 1 1 d . . .
H3A H -0.0083 0.0504 0.4459 0.019 Uiso 1 1 calc R . .
H3B H 0.1141 -0.1061 0.4474 0.019 Uiso 1 1 calc R . .
C4 C 0.3621(2) 0.22231(16) 0.52214(6) 0.0189(3) Uani 1 1 d . . .
H4A H 0.2527 0.1925 0.5419 0.023 Uiso 1 1 calc R . .
C5 C 0.5038(2) 0.31479(17) 0.55018(6) 0.0210(3) Uani 1 1 d . . .
H5A H 0.4918 0.3483 0.5898 0.025 Uiso 1 1 calc R . .
C6 C 0.6657(2) 0.36052(16) 0.52133(6) 0.0205(3) Uani 1 1 d . . .
H6A H 0.7599 0.4255 0.5417 0.025 Uiso 1 1 calc R . .
C7 C 0.6911(2) 0.31321(16) 0.46401(6) 0.0183(3) Uani 1 1 d . . .
H7A H 0.8006 0.3447 0.4446 0.022 Uiso 1 1 calc R . .
C8 C 0.36746(18) 0.06767(15) 0.37213(6) 0.0142(3) Uani 1 1 d . . .
C9 C 0.26856(19) 0.08010(15) 0.42180(6) 0.0150(3) Uani 1 1 d . . .
C10 C 0.38270(19) 0.17298(15) 0.46361(6) 0.0157(3) Uani 1 1 d . . .
C11 C 0.54945(19) 0.21723(15) 0.43571(6) 0.0155(3) Uani 1 1 d . . .
C12 C 0.45596(18) -0.09300(15) 0.28282(6) 0.0139(3) Uani 1 1 d . . .
H12A H 0.4221 -0.1972 0.2679 0.017 Uiso 1 1 calc R . .
H12B H 0.5874 -0.0971 0.3041 0.017 Uiso 1 1 calc R . .
C13 C 0.45617(18) 0.01852(14) 0.22961(6) 0.0133(3) Uani 1 1 d . . .
C14 C 0.6298(2) -0.01932(16) 0.19483(6) 0.0177(3) Uani 1 1 d . . .
C15 C 0.27071(19) 0.00504(16) 0.18781(6) 0.0176(3) Uani 1 1 d . . .
H15A H 0.2757 0.0773 0.1547 0.026 Uiso 1 1 calc R . .
H15B H 0.1586 0.0288 0.2097 0.026 Uiso 1 1 calc R . .
H15C H 0.2586 -0.0996 0.1721 0.026 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 C14 1.3456(16) . ?
F2 C14 1.3377(16) . ?
F3 C14 1.3510(16) . ?
O1 C13 1.4075(15) . ?
O1 H1A 0.8400 . ?
N1 C1 1.2914(17) . ?
N1 C2 1.4767(16) . ?
N2 C11 1.3826(17) . ?
N2 C8 1.3882(17) . ?
N2 H2A 0.8800 . ?
C1 C8 1.4525(18) . ?
C1 C12 1.5091(17) . ?
C2 C3 1.5300(18) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C3 C9 1.4950(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.378(2) . ?
C4 C10 1.4071(19) . ?
C4 H4A 0.9500 . ?
C5 C6 1.405(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.383(2) . ?
C6 H6A 0.9500 . ?
C7 C11 1.3983(19) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3694(18) . ?
C9 C10 1.4256(18) . ?
C10 C11 1.4186(19) . ?
C12 C13 1.5441(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.5258(17) . ?
C13 C14 1.5311(18) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C13 O1 H1A 109.5 . . ?
C1 N1 C2 117.18(11) . . ?
C11 N2 C8 107.78(11) . . ?
C11 N2 H2A 126.1 . . ?
C8 N2 H2A 126.1 . . ?
N1 C1 C8 120.34(12) . . ?
N1 C1 C12 118.98(11) . . ?
C8 C1 C12 120.60(11) . . ?
N1 C2 C3 115.29(11) . . ?
N1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
N1 C2 H2C 108.5 . . ?
C3 C2 H2C 108.5 . . ?
H2B C2 H2C 107.5 . . ?
C9 C3 C2 108.08(11) . . ?
C9 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C9 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C5 C4 C10 118.62(13) . . ?
C5 C4 H4A 120.7 . . ?
C10 C4 H4A 120.7 . . ?
C4 C5 C6 121.28(13) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C7 C6 C5 121.57(13) . . ?
C7 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
C6 C7 C11 117.41(13) . . ?
C6 C7 H7A 121.3 . . ?
C11 C7 H7A 121.3 . . ?
C9 C8 N2 110.07(11) . . ?
C9 C8 C1 121.81(12) . . ?
N2 C8 C1 126.78(11) . . ?
C8 C9 C10 107.25(12) . . ?
C8 C9 C3 119.17(12) . . ?
C10 C9 C3 133.28(12) . . ?
C4 C10 C11 119.31(12) . . ?
C4 C10 C9 134.05(13) . . ?
C11 C10 C9 106.63(11) . . ?
N2 C11 C7 130.02(12) . . ?
N2 C11 C10 108.21(11) . . ?
C7 C11 C10 121.77(12) . . ?
C1 C12 C13 111.08(10) . . ?
C1 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C1 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O1 C13 C15 113.19(10) . . ?
O1 C13 C14 106.85(10) . . ?
C15 C13 C14 108.89(11) . . ?
O1 C13 C12 107.42(10) . . ?
C15 C13 C12 111.71(11) . . ?
C14 C13 C12 108.58(10) . . ?
F2 C14 F1 106.60(11) . . ?
F2 C14 F3 106.55(11) . . ?
F1 C14 F3 106.31(11) . . ?
F2 C14 C13 112.83(11) . . ?
F1 C14 C13 111.87(11) . . ?
F3 C14 C13 112.24(11) . . ?
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 . . ?

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
C2 N1 C1 C8 7.44(18) . . . . ?
C2 N1 C1 C12 -175.89(11) . . . . ?
C1 N1 C2 C3 -40.90(16) . . . . ?
N1 C2 C3 C9 47.18(15) . . . . ?
C10 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C7 -0.9(2) . . . . ?
C5 C6 C7 C11 -0.2(2) . . . . ?
C11 N2 C8 C9 -1.45(15) . . . . ?
C11 N2 C8 C1 -168.33(12) . . . . ?
N1 C1 C8 C9 17.52(19) . . . . ?
C12 C1 C8 C9 -159.09(12) . . . . ?
N1 C1 C8 N2 -177.01(12) . . . . ?
C12 C1 C8 N2 6.4(2) . . . . ?
N2 C8 C9 C10 -0.03(15) . . . . ?
C1 C8 C9 C10 167.61(12) . . . . ?
N2 C8 C9 C3 -174.62(11) . . . . ?
C1 C8 C9 C3 -6.98(19) . . . . ?
C2 C3 C9 C8 -23.83(16) . . . . ?
C2 C3 C9 C10 163.27(14) . . . . ?
C5 C4 C10 C11 1.1(2) . . . . ?
C5 C4 C10 C9 -179.65(14) . . . . ?
C8 C9 C10 C4 -177.84(15) . . . . ?
C3 C9 C10 C4 -4.3(3) . . . . ?
C8 C9 C10 C11 1.45(15) . . . . ?
C3 C9 C10 C11 174.97(14) . . . . ?
C8 N2 C11 C7 -178.38(14) . . . . ?
C8 N2 C11 C10 2.35(14) . . . . ?
C6 C7 C11 N2 -177.40(13) . . . . ?
C6 C7 C11 C10 1.8(2) . . . . ?
C4 C10 C11 N2 177.07(12) . . . . ?
C9 C10 C11 N2 -2.35(14) . . . . ?
C4 C10 C11 C7 -2.3(2) . . . . ?
C9 C10 C11 C7 178.30(12) . . . . ?
N1 C1 C12 C13 97.48(14) . . . . ?
C8 C1 C12 C13 -85.86(14) . . . . ?
C1 C12 C13 O1 53.83(13) . . . . ?
C1 C12 C13 C15 -70.85(13) . . . . ?
C1 C12 C13 C14 169.05(11) . . . . ?
O1 C13 C14 F2 55.36(14) . . . . ?
C15 C13 C14 F2 177.94(11) . . . . ?
C12 C13 C14 F2 -60.23(14) . . . . ?
O1 C13 C14 F1 -64.83(13) . . . . ?
C15 C13 C14 F1 57.75(14) . . . . ?
C12 C13 C14 F1 179.58(10) . . . . ?
O1 C13 C14 F3 175.76(10) . . . . ?
C15 C13 C14 F3 -61.66(14) . . . . ?
C12 C13 C14 F3 60.17(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N1 0.84 1.95 2.7028(14) 148.6 2
N2 H2A O1 0.88 2.41 2.8596(14) 112.4 .
N2 H2A F3 0.88 2.46 3.1782(14) 139.0 2_655

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_20170922
_audit_block_doi                 10.5517/ccdc.csd.cc1z25w3
_database_code_depnum_ccdc_archive 'CCDC 1819355'
_audit_update_record             
;
2018-01-25 deposited with the CCDC.
2018-02-12 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   C2/c

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

_cell_length_a                   17.9537(9)
_cell_length_b                   7.1369(3)
_cell_length_c                   21.8227(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.706(3)
_cell_angle_gamma                90.00
_cell_volume                     2579.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    5784
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      29.74

_exptl_crystal_description       block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9411
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(1)
_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            3711
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         29.89
_reflns_number_total             3711
_reflns_number_gt                2516
_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)+(0.1027P)²+0.5825P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3711
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1903
_refine_ls_wR_factor_gt          0.1685
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
F1A F 1.0016(2) 0.2262(10) 0.1695(6) 0.154(3) Uani 0.486(9) 1 d P A 1
F2A F 0.9777(3) 0.0753(17) 0.0829(2) 0.151(4) Uani 0.486(9) 1 d P A 1
F3A F 0.9917(3) 0.027(2) 0.1856(2) 0.156(4) Uani 0.486(9) 1 d P A 1
F1B F 0.9922(3) 0.2124(13) 0.1140(6) 0.180(4) Uani 0.514(9) 1 d P A 2
F2B F 0.9559(4) -0.0572(15) 0.0886(4) 0.189(4) Uani 0.514(9) 1 d P A 2
F3B F 0.9802(5) -0.0523(11) 0.1675(5) 0.150(3) Uani 0.514(9) 1 d P A 2
O1 O 0.82905(7) 0.1833(2) 0.05141(5) 0.0759(4) Uani 1 1 d . . .
O2 O 0.79979(10) 0.1727(2) 0.37965(6) 0.0913(5) Uani 1 1 d . . .
N1 N 0.70102(7) 0.1924(2) 0.08690(6) 0.0611(3) Uani 1 1 d . . .
H1A H 0.7180 0.1990 0.0551 0.073 Uiso 1 1 calc R . .
C1 C 0.95447(11) 0.0863(3) 0.12899(9) 0.0792(5) Uani 1 1 d . . .
C2 C 0.86557(8) 0.1350(2) 0.11016(7) 0.0534(3) Uani 1 1 d . A .
C3 C 0.83488(8) 0.1180(2) 0.15920(6) 0.0516(3) Uani 1 1 d . . .
H3A H 0.8696 0.0836 0.2018 0.062 Uiso 1 1 calc R A .
C4 C 0.75349(8) 0.15088(19) 0.14701(6) 0.0503(3) Uani 1 1 d . A .
C5 C 0.61529(9) 0.2277(3) 0.07146(9) 0.0743(5) Uani 1 1 d . . .
H5A H 0.5844 0.2091 0.0244 0.089 Uiso 1 1 calc R . .
H5B H 0.6077 0.3561 0.0825 0.089 Uiso 1 1 calc R . .
C6 C 0.58637(10) 0.0945(3) 0.11127(9) 0.0757(5) Uani 1 1 d . . .
H6A H 0.5311 0.1242 0.1048 0.091 Uiso 1 1 calc R . .
H6B H 0.5877 -0.0330 0.0963 0.091 Uiso 1 1 calc R . .
C7 C 0.63963(10) 0.1107(2) 0.18340(8) 0.0636(4) Uani 1 1 d . A .
C8 C 0.61186(12) 0.1001(3) 0.23435(10) 0.0780(5) Uani 1 1 d . . .
H8A H 0.5571 0.0804 0.2237 0.094 Uiso 1 1 calc R . .
C9 C 0.66240(13) 0.1177(3) 0.30002(10) 0.0791(5) Uani 1 1 d . . .
H9A H 0.6419 0.1091 0.3331 0.095 Uiso 1 1 calc R . .
C10 C 0.74370(12) 0.1482(2) 0.31662(8) 0.0680(4) Uani 1 1 d . . .
C11 C 0.77414(10) 0.1570(2) 0.26674(7) 0.0593(4) Uani 1 1 d . A .
H11A H 0.8291 0.1748 0.2778 0.071 Uiso 1 1 calc R . .
C12 C 0.72247(9) 0.13913(19) 0.20065(7) 0.0540(3) Uani 1 1 d . . .
C13 C 0.77252(17) 0.1791(3) 0.43302(10) 0.1050(8) Uani 1 1 d . . .
H13A H 0.8179 0.1960 0.4742 0.158 Uiso 1 1 calc R . .
H13B H 0.7457 0.0638 0.4344 0.158 Uiso 1 1 calc R . .
H13C H 0.7356 0.2817 0.4263 0.158 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
F1A C1 1.384(5) . ?
F2A C1 1.232(4) . ?
F3A C1 1.231(5) . ?
F1B C1 1.243(5) . ?
F2B C1 1.359(5) . ?
F3B C1 1.265(5) . ?
O1 C2 1.2423(16) . ?
O2 C10 1.367(2) . ?
O2 C13 1.428(2) . ?
N1 C4 1.3198(17) . ?
N1 C5 1.465(2) . ?
N1 H1A 0.8600 . ?
C1 C2 1.527(2) . ?
C2 C3 1.3853(18) . ?
C3 C4 1.4003(19) . ?
C3 H3A 0.9300 . ?
C4 C12 1.4800(17) . ?
C5 C6 1.509(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.498(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.385(2) . ?
C7 C12 1.401(2) . ?
C8 C9 1.374(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.379(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.395(2) . ?
C11 C12 1.387(2) . ?
C11 H11A 0.9300 . ?
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
C10 O2 C13 118.27(18) . . ?
C4 N1 C5 123.42(12) . . ?
C4 N1 H1A 118.3 . . ?
C5 N1 H1A 118.3 . . ?
F3A C1 F2A 125.0(4) . . ?
F3A C1 F1B 111.9(7) . . ?
F2A C1 F1B 56.0(4) . . ?
F3A C1 F3B 31.3(6) . . ?
F2A C1 F3B 110.0(6) . . ?
F1B C1 F3B 130.2(5) . . ?
F3A C1 F2B 104.6(8) . . ?
F2A C1 F2B 47.5(4) . . ?
F1B C1 F2B 103.1(5) . . ?
F3B C1 F2B 75.4(8) . . ?
F3A C1 F1A 69.3(8) . . ?
F2A C1 F1A 104.5(5) . . ?
F1B C1 F1A 52.0(4) . . ?
F3B C1 F1A 99.4(7) . . ?
F2B C1 F1A 143.0(4) . . ?
F3A C1 C2 117.1(3) . . ?
F2A C1 C2 116.3(2) . . ?
F1B C1 C2 112.5(3) . . ?
F3B C1 C2 115.6(4) . . ?
F2B C1 C2 106.1(3) . . ?
F1A C1 C2 109.0(3) . . ?
O1 C2 C3 127.78(13) . . ?
O1 C2 C1 114.92(12) . . ?
C3 C2 C1 117.29(13) . . ?
C2 C3 C4 122.39(12) . . ?
C2 C3 H3A 118.8 . . ?
C4 C3 H3A 118.8 . . ?
N1 C4 C3 121.24(12) . . ?
N1 C4 C12 117.16(12) . . ?
C3 C4 C12 121.60(12) . . ?
N1 C5 C6 108.88(14) . . ?
N1 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
N1 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C7 C6 C5 109.53(14) . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C12 117.77(16) . . ?
C8 C7 C6 123.89(16) . . ?
C12 C7 C6 118.33(13) . . ?
C9 C8 C7 122.33(17) . . ?
C9 C8 H8A 118.8 . . ?
C7 C8 H8A 118.8 . . ?
C8 C9 C10 119.62(14) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
O2 C10 C9 125.36(14) . . ?
O2 C10 C11 114.90(16) . . ?
C9 C10 C11 119.73(16) . . ?
C12 C11 C10 120.06(16) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C11 C12 C7 120.48(13) . . ?
C11 C12 C4 120.82(13) . . ?
C7 C12 C4 118.70(13) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 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
F3A C1 C2 O1 -175.7(8) . . . . ?
F2A C1 C2 O1 -9.4(7) . . . . ?
F1B C1 C2 O1 52.5(7) . . . . ?
F3B C1 C2 O1 -140.7(6) . . . . ?
F2B C1 C2 O1 -59.5(6) . . . . ?
F1A C1 C2 O1 108.4(6) . . . . ?
F3A C1 C2 C3 3.4(8) . . . . ?
F2A C1 C2 C3 169.7(7) . . . . ?
F1B C1 C2 C3 -128.4(7) . . . . ?
F3B C1 C2 C3 38.3(6) . . . . ?
F2B C1 C2 C3 119.6(6) . . . . ?
F1A C1 C2 C3 -72.6(6) . . . . ?
O1 C2 C3 C4 1.8(2) . . . . ?
C1 C2 C3 C4 -177.15(15) . . . . ?
C5 N1 C4 C3 179.91(15) . . . . ?
C5 N1 C4 C12 0.4(2) . . . . ?
C2 C3 C4 N1 2.9(2) . . . . ?
C2 C3 C4 C12 -177.62(13) . . . . ?
C4 N1 C5 C6 -38.3(2) . . . . ?
N1 C5 C6 C7 53.96(19) . . . . ?
C5 C6 C7 C8 142.50(17) . . . . ?
C5 C6 C7 C12 -37.2(2) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
C6 C7 C8 C9 -179.25(16) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C13 O2 C10 C9 -4.1(3) . . . . ?
C13 O2 C10 C11 175.57(16) . . . . ?
C8 C9 C10 O2 178.28(17) . . . . ?
C8 C9 C10 C11 -1.3(2) . . . . ?
O2 C10 C11 C12 -178.26(13) . . . . ?
C9 C10 C11 C12 1.4(2) . . . . ?
C10 C11 C12 C7 -0.5(2) . . . . ?
C10 C11 C12 C4 179.10(13) . . . . ?
C8 C7 C12 C11 -0.4(2) . . . . ?
C6 C7 C12 C11 179.33(14) . . . . ?
C8 C7 C12 C4 179.99(14) . . . . ?
C6 C7 C12 C4 -0.3(2) . . . . ?
N1 C4 C12 C11 -158.98(14) . . . . ?
C3 C4 C12 C11 21.5(2) . . . . ?
N1 C4 C12 C7 20.64(19) . . . . ?
C3 C4 C12 C7 -158.88(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.86 2.30 2.9886(16) 136.7 7_655

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.89
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.058
