# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1859486'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-08-27 downloaded from the CCDC.
;
_audit_creation_date             2017-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 Br N2 O3'
_chemical_formula_sum            'C19 H15 Br N2 O3'
_chemical_formula_weight         399.24
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.499(3)
_cell_length_b                   20.581(6)
_cell_length_c                   8.367(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.054(3)
_cell_angle_gamma                90
_cell_volume                     1718.9(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1964
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.75
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.830
_shelx_estimated_absorpt_T_min   0.714
_exptl_absorpt_coefficient_mu    2.412
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0675 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.8413.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15229
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         1.977
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2031
_reflns_number_total             3039
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3039
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+0.8078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0814
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.58032(4) 0.41780(2) 0.59094(5) 0.05047(15) Uani 1 1 d . . . . .
C1 C 0.7955(4) 0.5502(2) -0.1392(5) 0.0676(13) Uani 1 1 d . . . . .
H1A H 0.7074 0.5389 -0.2101 0.101 Uiso 1 1 calc GR . . . .
H1B H 0.8592 0.5427 -0.1984 0.101 Uiso 1 1 calc GR . . . .
H1C H 0.7973 0.5953 -0.1089 0.101 Uiso 1 1 calc GR . . . .
C2 C 0.8300(4) 0.5104(2) 0.0126(5) 0.0489(10) Uani 1 1 d . . . . .
C3 C 0.8583(4) 0.47800(19) 0.1338(5) 0.0453(10) Uani 1 1 d . . . . .
C4 C 0.9003(4) 0.43981(18) 0.2889(5) 0.0443(10) Uani 1 1 d . . . . .
H4A H 0.9759 0.4612 0.3687 0.053 Uiso 1 1 calc R . . . .
H4B H 0.9300 0.3974 0.2645 0.053 Uiso 1 1 calc R . . . .
C5 C 0.7863(3) 0.43062(16) 0.3717(4) 0.0361(9) Uani 1 1 d . . . . .
C6 C 0.7452(4) 0.49743(19) 0.3987(4) 0.0370(9) Uani 1 1 d . . . . .
C7 C 0.8402(4) 0.39757(15) 0.5462(4) 0.0342(9) Uani 1 1 d . . . . .
C8 C 0.9715(4) 0.37488(17) 0.6048(4) 0.0392(9) Uani 1 1 d . . . . .
H8 H 1.0275 0.3810 0.5390 0.047 Uiso 1 1 calc R . . . .
C9 C 1.0210(4) 0.34364(16) 0.7572(5) 0.0430(10) Uani 1 1 d . . . . .
H9 H 1.1090 0.3289 0.7948 0.052 Uiso 1 1 calc R . . . .
C10 C 0.9371(4) 0.33504(16) 0.8509(4) 0.0392(9) Uani 1 1 d . . . . .
C11 C 0.8077(4) 0.35725(16) 0.8021(5) 0.0419(9) Uani 1 1 d . . . . .
H11 H 0.7533 0.3512 0.8699 0.050 Uiso 1 1 calc R . . . .
C12 C 0.7600(3) 0.38888(16) 0.6496(4) 0.0355(9) Uani 1 1 d . . . . .
C13 C 0.6719(3) 0.39176(17) 0.2518(4) 0.0355(9) Uani 1 1 d . . . . .
C14 C 0.5703(4) 0.42205(19) 0.1278(4) 0.0483(10) Uani 1 1 d . . . . .
H14 H 0.5690 0.4671 0.1204 0.058 Uiso 1 1 calc R . . . .
C15 C 0.4716(4) 0.38672(19) 0.0156(5) 0.0519(11) Uani 1 1 d . . . . .
H15 H 0.4050 0.4081 -0.0677 0.062 Uiso 1 1 calc R . . . .
C16 C 0.4700(4) 0.31998(19) 0.0250(5) 0.0434(10) Uani 1 1 d . . . . .
C17 C 0.5714(4) 0.28893(18) 0.1461(5) 0.0505(11) Uani 1 1 d . . . . .
H17 H 0.5725 0.2438 0.1533 0.061 Uiso 1 1 calc R . . . .
C18 C 0.6718(4) 0.32515(18) 0.2572(5) 0.0461(10) Uani 1 1 d . . . . .
H18 H 0.7407 0.3038 0.3373 0.055 Uiso 1 1 calc R . . . .
C19 C 0.3501(4) 0.2214(2) -0.0694(6) 0.0693(13) Uani 1 1 d . . . . .
H19A H 0.2664 0.2071 -0.1462 0.104 Uiso 1 1 calc GR . . . .
H19B H 0.3521 0.2120 0.0437 0.104 Uiso 1 1 calc GR . . . .
H19C H 0.4224 0.1990 -0.0935 0.104 Uiso 1 1 calc GR . . . .
N1 N 0.7234(3) 0.55028(17) 0.4207(4) 0.0534(9) Uani 1 1 d . . . . .
N2 N 0.9864(5) 0.30046(16) 1.0127(5) 0.0578(10) Uani 1 1 d . . . . .
O1 O 0.3643(3) 0.28956(13) -0.0877(3) 0.0602(8) Uani 1 1 d . . . . .
O2 O 0.9117(4) 0.29395(17) 1.0959(4) 0.0959(13) Uani 1 1 d . . . . .
O3 O 1.0981(4) 0.27873(19) 1.0528(4) 0.1005(13) 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
Br1 C12 1.892(3) . ?
C1 C2 1.459(5) . ?
C2 C3 1.173(5) . ?
C3 C4 1.463(5) . ?
C4 C5 1.569(5) . ?
C5 C6 1.479(5) . ?
C5 C7 1.550(5) . ?
C5 C13 1.531(5) . ?
C6 N1 1.138(4) . ?
C7 C8 1.392(5) . ?
C7 C12 1.394(5) . ?
C8 C9 1.378(5) . ?
C9 C10 1.359(5) . ?
C10 C11 1.371(5) . ?
C10 N2 1.474(5) . ?
C11 C12 1.380(5) . ?
C13 C14 1.385(5) . ?
C13 C18 1.372(5) . ?
C14 C15 1.372(5) . ?
C15 C16 1.376(5) . ?
C16 C17 1.379(5) . ?
C16 O1 1.365(4) . ?
C17 C18 1.387(5) . ?
C19 O1 1.424(4) . ?
N2 O2 1.206(4) . ?
N2 O3 1.202(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 179.4(5) . . ?
C2 C3 C4 176.8(4) . . ?
C3 C4 C5 113.3(3) . . ?
C6 C5 C4 104.7(3) . . ?
C6 C5 C7 107.6(3) . . ?
C6 C5 C13 112.3(3) . . ?
C7 C5 C4 111.3(3) . . ?
C13 C5 C4 109.0(3) . . ?
C13 C5 C7 111.8(3) . . ?
N1 C6 C5 174.7(4) . . ?
C8 C7 C5 120.8(3) . . ?
C8 C7 C12 117.5(3) . . ?
C12 C7 C5 121.8(3) . . ?
C9 C8 C7 122.0(3) . . ?
C10 C9 C8 117.9(4) . . ?
C9 C10 C11 122.9(3) . . ?
C9 C10 N2 119.2(4) . . ?
C11 C10 N2 117.9(4) . . ?
C10 C11 C12 118.4(3) . . ?
C7 C12 Br1 123.0(3) . . ?
C11 C12 Br1 115.8(3) . . ?
C11 C12 C7 121.2(3) . . ?
C14 C13 C5 121.5(3) . . ?
C18 C13 C5 120.6(3) . . ?
C18 C13 C14 117.8(3) . . ?
C15 C14 C13 121.2(4) . . ?
C14 C15 C16 120.7(4) . . ?
C15 C16 C17 119.0(4) . . ?
O1 C16 C15 116.1(3) . . ?
O1 C16 C17 124.9(3) . . ?
C16 C17 C18 119.8(3) . . ?
C13 C18 C17 121.5(3) . . ?
O2 N2 C10 118.6(4) . . ?
O3 N2 C10 118.0(4) . . ?
O3 N2 O2 123.4(4) . . ?
C16 O1 C19 117.8(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_kl128_a
_database_code_depnum_ccdc_archive 'CCDC 1859487'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 F3 N2 O4'
_chemical_formula_sum            'C18 H13 F3 N2 O4'
_chemical_formula_weight         378.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   18.290(2)
_cell_length_b                   10.7507(14)
_cell_length_c                   9.2330(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.659(2)
_cell_angle_gamma                90
_cell_volume                     1794.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6287
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.73

_exptl_crystal_description       platy
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23928
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.204
_diffrn_reflns_theta_max         33.126
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6515
_reflns_number_gt                3904
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1217P)²+0.3211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6515
_refine_ls_number_parameters     255
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.2452
_refine_ls_wR_factor_gt          0.2152
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.120
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9714(3) 0.6512(5) 0.3697(7) 0.1495(17) Uani 0.639(3) 1 d . U P A 1
F2 F 1.03078(16) 0.5043(5) 0.3085(8) 0.1596(16) Uani 0.639(3) 1 d . U P A 1
F3 F 0.9709(4) 0.6198(7) 0.1504(6) 0.1688(19) Uani 0.639(3) 1 d . U P A 1
F1A F 1.0068(8) 0.5808(14) 0.3772(12) 0.1688(19) Uani 0.361(3) 1 d . U P A 2
F2A F 1.0018(5) 0.5368(10) 0.1529(12) 0.1495(17) Uani 0.361(3) 1 d . U P A 2
F3A F 0.9424(3) 0.6837(9) 0.2247(15) 0.1596(16) Uani 0.361(3) 1 d . U P A 2
O1 O 0.47704(11) 0.74353(19) -0.0672(2) 0.0979(6) Uani 1 1 d . . . . .
O2 O 0.40489(9) 0.6620(2) 0.0652(2) 0.1007(6) Uani 1 1 d . . . . .
O3 O 0.73306(8) 0.67958(12) 0.50575(15) 0.0652(4) Uani 1 1 d . . . . .
O4 O 0.76891(8) 0.51600(14) 0.64818(14) 0.0659(4) Uani 1 1 d . . . . .
N1 N 0.46582(9) 0.67861(14) 0.03376(19) 0.0605(4) Uani 1 1 d . . . . .
N2 N 0.39649(11) 0.4570(3) 0.3082(3) 0.0939(7) Uani 1 1 d . . . . .
C1 C 0.71699(9) 0.47181(14) 0.40570(18) 0.0455(3) Uani 1 1 d . . . . .
H1 H 0.7006 0.3974 0.4532 0.055 Uiso 1 1 calc R U . . .
C2 C 0.78308(9) 0.43543(15) 0.33238(18) 0.0479(3) Uani 1 1 d . . . . .
C3 C 0.78315(13) 0.32105(18) 0.2618(3) 0.0677(5) Uani 1 1 d . . . . .
H3 H 0.7430 0.2677 0.2601 0.081 Uiso 1 1 calc R U . . .
C4 C 0.84268(16) 0.2861(2) 0.1941(3) 0.0847(7) Uani 1 1 d . . . . .
H4 H 0.8420 0.2096 0.1469 0.102 Uiso 1 1 calc R U . . .
C5 C 0.90231(13) 0.3630(2) 0.1958(3) 0.0800(7) Uani 1 1 d . . . . .
H5 H 0.9423 0.3387 0.1510 0.096 Uiso 1 1 calc R U . . .
C6 C 0.90268(11) 0.4758(2) 0.2641(3) 0.0693(5) Uani 1 1 d . . . . .
C7 C 0.84378(10) 0.51299(18) 0.3332(2) 0.0567(4) Uani 1 1 d . . . . .
H7 H 0.8451 0.5898 0.3799 0.068 Uiso 1 1 calc R U . . .
C8 C 0.96731(16) 0.5621(4) 0.2651(4) 0.1054(10) Uani 1 1 d . . . . .
C9 C 0.65171(8) 0.52067(14) 0.30023(17) 0.0439(3) Uani 1 1 d . . . . .
C10 C 0.65993(9) 0.60080(16) 0.18555(19) 0.0529(4) Uani 1 1 d . . . . .
H10 H 0.7072 0.6211 0.1675 0.063 Uiso 1 1 calc R U . . .
C11 C 0.59916(10) 0.65076(16) 0.09810(19) 0.0543(4) Uani 1 1 d . . . . .
H11 H 0.6053 0.7046 0.0220 0.065 Uiso 1 1 calc R U . . .
C12 C 0.52925(9) 0.62003(14) 0.12485(17) 0.0473(3) Uani 1 1 d . . . . .
C13 C 0.51862(9) 0.53795(15) 0.23677(18) 0.0471(3) Uani 1 1 d . . . . .
C14 C 0.58079(9) 0.48878(15) 0.32336(18) 0.0471(3) Uani 1 1 d . . . . .
H14 H 0.5747 0.4335 0.3981 0.057 Uiso 1 1 calc R U . . .
C15 C 0.44812(10) 0.4979(2) 0.2700(2) 0.0625(5) Uani 1 1 d . . . . .
C16 C 0.73950(9) 0.56926(16) 0.52455(18) 0.0498(4) Uani 1 1 d . . . . .
C17 C 0.78947(16) 0.6001(3) 0.7723(2) 0.0874(7) Uani 1 1 d . . . . .
H17A H 0.8331 0.6474 0.7586 0.105 Uiso 1 1 calc R U . . .
H17B H 0.7495 0.6581 0.7791 0.105 Uiso 1 1 calc R U . . .
C18 C 0.8042(3) 0.5286(4) 0.9030(3) 0.1362(15) Uani 1 1 d . . . . .
H18A H 0.7604 0.4840 0.9174 0.204 Uiso 1 1 calc R U . . .
H18B H 0.8188 0.5829 0.9848 0.204 Uiso 1 1 calc R U . . .
H18C H 0.8433 0.4706 0.8949 0.204 Uiso 1 1 calc R U . . .


_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 1.354(5) . ?
F2 C8 1.325(5) . ?
F3 C8 1.238(5) . ?
F1A C8 1.186(10) . ?
F2A C8 1.320(8) . ?
F3A C8 1.415(10) . ?
O1 N1 1.206(2) . ?
O2 N1 1.206(2) . ?
O3 C16 1.202(2) . ?
O4 C16 1.317(2) . ?
O4 C17 1.464(3) . ?
N1 C12 1.468(2) . ?
N2 C15 1.144(3) . ?
C1 C9 1.516(2) . ?
C1 C2 1.523(2) . ?
C1 C16 1.528(2) . ?
C1 H1 0.9800 . ?
C2 C7 1.387(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(3) . ?
C6 C8 1.502(4) . ?
C7 H7 0.9300 . ?
C9 C14 1.389(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.380(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.395(2) . ?
C13 C14 1.392(2) . ?
C13 C15 1.436(2) . ?
C14 H14 0.9300 . ?
C17 C18 1.422(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C16 O4 C17 115.66(16) . . ?
O1 N1 O2 122.82(18) . . ?
O1 N1 C12 118.62(17) . . ?
O2 N1 C12 118.53(17) . . ?
C9 C1 C2 113.86(13) . . ?
C9 C1 C16 108.94(13) . . ?
C2 C1 C16 110.44(12) . . ?
C9 C1 H1 107.8 . . ?
C2 C1 H1 107.8 . . ?
C16 C1 H1 107.8 . . ?
C7 C2 C3 118.46(17) . . ?
C7 C2 C1 122.09(14) . . ?
C3 C2 C1 119.45(16) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 C8 120.1(2) . . ?
C7 C6 C8 118.9(2) . . ?
C2 C7 C6 119.93(18) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
F1A C8 F2A 114.8(8) . . ?
F3 C8 F2 109.6(4) . . ?
F3 C8 F1 104.6(5) . . ?
F2 C8 F1 99.5(4) . . ?
F1A C8 F3A 101.8(8) . . ?
F2A C8 F3A 99.0(7) . . ?
F1A C8 C6 119.0(5) . . ?
F3 C8 C6 116.6(4) . . ?
F2A C8 C6 109.6(4) . . ?
F2 C8 C6 111.4(4) . . ?
F1 C8 C6 113.6(3) . . ?
F3A C8 C6 110.3(3) . . ?
C14 C9 C10 118.72(15) . . ?
C14 C9 C1 118.62(14) . . ?
C10 C9 C1 122.59(14) . . ?
C11 C10 C9 121.10(15) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 119.27(15) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 121.40(15) . . ?
C11 C12 N1 117.95(15) . . ?
C13 C12 N1 120.63(15) . . ?
C14 C13 C12 118.22(14) . . ?
C14 C13 C15 116.47(15) . . ?
C12 C13 C15 125.31(16) . . ?
C9 C14 C13 121.27(15) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
N2 C15 C13 172.0(2) . . ?
O3 C16 O4 124.92(16) . . ?
O3 C16 C1 124.26(15) . . ?
O4 C16 C1 110.79(14) . . ?
C18 C17 O4 108.9(2) . . ?
C18 C17 H17A 109.9 . . ?
O4 C17 H17A 109.9 . . ?
C18 C17 H17B 109.9 . . ?
O4 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.048

