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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_10348
_audit_block_doi                 10.5517/ccdc.csd.cc22hz5r
_database_code_depnum_ccdc_archive 'CCDC 1921974'
loop_
_audit_author_name
_audit_author_address
'Wenting Zhang'
;FUzhou University
China
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 F6 N2 O4'
_chemical_formula_weight         486.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   6.9606(6)
_cell_length_b                   15.3498(10)
_cell_length_c                   9.8404(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.958(8)
_cell_angle_gamma                90.00
_cell_volume                     1048.87(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2049
_cell_measurement_theta_min      0.764
_cell_measurement_theta_max      0.861

_exptl_crystal_description       Bulk
_exptl_crystal_colour            transparnet
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_T_max  71.387
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6045
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.35
_diffrn_reflns_theta_max         71.39
_reflns_number_total             2016
_reflns_number_gt                1323
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0826P)²+0.0482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2016
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1735
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2411(3) 0.58341(10) 0.63061(18) 0.0554(5) Uani 1 1 d . . .
N1 N 0.2213(3) 0.62699(14) 0.4117(2) 0.0569(6) Uani 1 1 d . . .
C3 C 0.2247(4) 0.64953(16) 0.5366(3) 0.0563(7) Uani 1 1 d . . .
C9 C 0.7271(4) 0.57665(16) 0.4069(3) 0.0576(7) Uani 1 1 d . . .
C6 C 0.7523(4) 0.52501(18) 0.6864(3) 0.0628(7) Uani 1 1 d . . .
H6 H 0.7610 0.5084 0.7775 0.075 Uiso 1 1 calc R . .
C7 C 0.7308(4) 0.61147(18) 0.6487(3) 0.0687(8) Uani 1 1 d . . .
H7 H 0.7240 0.6539 0.7157 0.082 Uiso 1 1 calc R . .
C1 C 0.2520(3) 0.50954(15) 0.5513(3) 0.0494(6) Uani 1 1 d . . .
C2 C 0.2396(3) 0.53579(16) 0.4172(3) 0.0523(6) Uani 1 1 d . . .
O2 O 0.6900(5) 0.68492(15) 0.2398(3) 0.1250(12) Uani 1 1 d . . .
C8 C 0.7194(4) 0.63593(17) 0.5135(3) 0.0672(8) Uani 1 1 d . . .
H8 H 0.7060 0.6948 0.4925 0.081 Uiso 1 1 calc R . .
C11 C 0.7257(5) 0.5454(2) 0.1501(3) 0.0858(10) Uani 1 1 d . . .
H11A H 0.8453 0.5142 0.1617 0.129 Uiso 1 1 calc R . .
H11B H 0.7199 0.5762 0.0650 0.129 Uiso 1 1 calc R . .
H11C H 0.6204 0.5051 0.1503 0.129 Uiso 1 1 calc R . .
C10 C 0.7128(5) 0.60841(18) 0.2633(3) 0.0729(8) Uani 1 1 d . . .
F3 F 0.0542(4) 0.80711(13) 0.4098(2) 0.1025(7) Uani 1 1 d . . .
F1 F 0.3590(3) 0.81252(12) 0.4240(2) 0.0976(7) Uani 1 1 d . . .
C4 C 0.2139(5) 0.73758(17) 0.5989(3) 0.0706(9) Uani 1 1 d . . .
H4A H 0.3258 0.7459 0.6619 0.085 Uiso 1 1 calc R . .
H4B H 0.1007 0.7403 0.6509 0.085 Uiso 1 1 calc R . .
C5 C 0.2051(6) 0.81011(18) 0.4980(3) 0.0754(10) Uani 1 1 d . . .
F2 F 0.2003(4) 0.88656(11) 0.5621(2) 0.1176(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0766(12) 0.0343(9) 0.0551(10) 0.0046(7) 0.0030(8) 0.0000(7)
N1 0.0801(15) 0.0362(11) 0.0542(13) 0.0003(9) 0.0021(10) 0.0020(9)
C3 0.0799(18) 0.0353(13) 0.0538(15) 0.0045(11) 0.0059(12) 0.0012(11)
C9 0.0616(16) 0.0365(13) 0.0736(18) 0.0059(12) -0.0023(13) -0.0030(11)
C6 0.0772(18) 0.0466(15) 0.0642(16) -0.0074(12) 0.0009(13) -0.0018(13)
C7 0.085(2) 0.0429(15) 0.078(2) -0.0134(14) -0.0019(15) 0.0005(13)
C1 0.0483(13) 0.0362(12) 0.0632(15) 0.0009(10) 0.0000(10) -0.0026(9)
C2 0.0525(14) 0.0398(13) 0.0643(16) 0.0005(11) 0.0015(11) 0.0004(10)
O2 0.233(3) 0.0404(13) 0.099(2) 0.0199(12) -0.011(2) 0.0052(16)
C8 0.0762(19) 0.0322(13) 0.092(2) -0.0013(13) -0.0047(16) -0.0028(12)
C11 0.128(3) 0.059(2) 0.070(2) 0.0154(16) 0.0051(19) 0.0049(18)
C10 0.096(2) 0.0405(15) 0.081(2) 0.0140(14) -0.0032(16) -0.0019(14)
F3 0.150(2) 0.0767(13) 0.0773(13) 0.0066(10) -0.0161(13) 0.0350(12)
F1 0.1563(19) 0.0610(12) 0.0777(13) 0.0045(9) 0.0240(13) -0.0204(11)
C4 0.123(3) 0.0381(15) 0.0507(16) 0.0015(11) 0.0068(16) 0.0052(15)
C5 0.143(3) 0.0355(14) 0.0475(15) -0.0024(11) 0.0073(18) 0.0038(16)
F2 0.249(3) 0.0344(9) 0.0697(12) -0.0044(8) 0.0154(14) 0.0104(12)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.372(3) . ?
O1 C1 1.382(3) . ?
N1 C3 1.276(3) . ?
N1 C2 1.406(3) . ?
C3 C4 1.488(3) . ?
C9 C1 1.390(3) 3_666 ?
C9 C8 1.392(4) . ?
C9 C10 1.492(4) . ?
C6 C7 1.384(4) . ?
C6 C2 1.386(4) 3_666 ?
C7 C8 1.379(4) . ?
C1 C2 1.376(4) . ?
C1 C9 1.390(3) 3_666 ?
C2 C6 1.386(4) 3_666 ?
O2 C10 1.205(3) . ?
C11 C10 1.482(4) . ?
F3 C5 1.316(4) . ?
F1 C5 1.336(4) . ?
C4 C5 1.490(4) . ?
C5 F2 1.334(3) . ?

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 O1 C1 103.38(19) . . ?
C3 N1 C2 103.7(2) . . ?
N1 C3 O1 116.3(2) . . ?
N1 C3 C4 130.2(2) . . ?
O1 C3 C4 113.5(2) . . ?
C1 C9 C8 114.1(3) 3_666 . ?
C1 C9 C10 126.2(3) 3_666 . ?
C8 C9 C10 119.8(2) . . ?
C7 C6 C2 117.2(3) . 3_666 ?
C8 C7 C6 121.2(3) . . ?
C2 C1 O1 107.4(2) . . ?
C2 C1 C9 124.1(2) . 3_666 ?
O1 C1 C9 128.5(2) . 3_666 ?
C1 C2 C6 120.3(2) . 3_666 ?
C1 C2 N1 109.1(2) . . ?
C6 C2 N1 130.5(2) 3_666 . ?
C7 C8 C9 123.1(3) . . ?
O2 C10 C11 120.4(3) . . ?
O2 C10 C9 119.9(3) . . ?
C11 C10 C9 119.7(2) . . ?
C3 C4 C5 113.9(2) . . ?
F3 C5 F2 107.3(3) . . ?
F3 C5 F1 106.0(2) . . ?
F2 C5 F1 106.3(3) . . ?
F3 C5 C4 114.0(3) . . ?
F2 C5 C4 110.1(2) . . ?
F1 C5 C4 112.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        71.39
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.073
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_10350
_audit_block_doi                 10.5517/ccdc.csd.cc22j2h6
_database_code_depnum_ccdc_archive 'CCDC 1922077'
loop_
_audit_author_name
_audit_author_address
'Wenting Zhang'
;FUzhou University
China
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8 Br F3 N2 S'
_chemical_formula_weight         313.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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

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

_cell_length_a                   8.8272(17)
_cell_length_b                   5.0631(10)
_cell_length_c                   12.707(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.248(16)
_cell_angle_gamma                90.00
_cell_volume                     566.36(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2214
_cell_measurement_theta_min      0.127
_cell_measurement_theta_max      0.254

_exptl_crystal_description       bulk
_exptl_crystal_colour            transparent
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    6.859
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.022
_exptl_absorpt_correction_T_max  71.250
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            3342
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0831
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.49
_diffrn_reflns_theta_max         71.25
_reflns_number_total             1796
_reflns_number_gt                1161
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.1190P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(8)
_refine_ls_number_reflns         1796
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.2252
_refine_ls_wR_factor_gt          0.1797
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.994
_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
Br1 Br 0.77314(18) 0.2649(4) 0.31561(9) 0.0901(7) Uani 1 1 d . . .
F1 F 0.8198(8) 0.7350(19) 1.1002(5) 0.083(2) Uani 1 1 d . . .
F2 F 0.7368(11) 0.3560(16) 1.0484(6) 0.093(3) Uani 1 1 d . . .
N2 N 0.9173(11) 0.228(2) 0.7235(7) 0.066(3) Uani 1 1 d . . .
H2A H 0.9104 0.3192 0.7814 0.079 Uiso 1 1 d R . .
H2B H 0.8783 0.0721 0.7334 0.079 Uiso 1 1 d R . .
N1 N 0.7416(11) 0.6893(19) 0.7590(7) 0.059(2) Uani 1 1 d . . .
H1 H 0.7933 0.8292 0.7755 0.071 Uiso 1 1 calc R . .
C5 C 0.8388(11) 0.362(2) 0.6384(8) 0.050(3) Uani 1 1 d . . .
C6 C 0.8450(12) 0.275(3) 0.5367(8) 0.063(3) Uani 1 1 d . . .
H6 H 0.9042 0.1285 0.5237 0.075 Uiso 1 1 calc R . .
C1 C 0.7668(13) 0.398(2) 0.4536(8) 0.055(3) Uani 1 1 d . . .
C4 C 0.7476(13) 0.584(2) 0.6548(8) 0.051(3) Uani 1 1 d . . .
C2 C 0.6762(14) 0.618(2) 0.4704(8) 0.061(3) Uani 1 1 d . . .
H2 H 0.6228 0.7010 0.4138 0.073 Uiso 1 1 calc R . .
C3 C 0.6667(13) 0.713(3) 0.5726(9) 0.067(3) Uani 1 1 d . . .
H3 H 0.6071 0.8589 0.5853 0.080 Uiso 1 1 calc R . .
C9 C 0.7863(14) 0.586(3) 1.0139(9) 0.063(3) Uani 1 1 d . . .
C8 C 0.6775(14) 0.722(3) 0.9386(8) 0.069(3) Uani 1 1 d . . .
H8A H 0.7123 0.9014 0.9281 0.082 Uiso 1 1 calc R . .
H8B H 0.5795 0.7319 0.9682 0.082 Uiso 1 1 calc R . .
F3 F 0.9174(10) 0.533(2) 0.9740(7) 0.108(3) Uani 1 1 d . . .
C7 C 0.6594(14) 0.581(2) 0.8318(8) 0.055(3) Uani 1 1 d . . .
S1AA S 0.5511(4) 0.3160(7) 0.8130(2) 0.0652(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.1129(12) 0.1100(14) 0.0458(6) -0.0078(8) -0.0041(6) -0.0287(11)
F1 0.094(5) 0.091(6) 0.059(3) -0.010(4) -0.021(3) -0.013(5)
F2 0.135(7) 0.070(6) 0.069(5) 0.016(4) -0.034(4) -0.014(5)
N2 0.085(6) 0.051(6) 0.056(5) 0.003(5) -0.025(4) 0.012(6)
N1 0.070(6) 0.051(6) 0.055(5) 0.001(4) -0.008(4) -0.002(5)
C5 0.047(5) 0.051(6) 0.050(5) 0.007(4) -0.008(4) -0.004(5)
C6 0.072(7) 0.060(7) 0.053(5) -0.011(6) -0.014(5) 0.012(7)
C1 0.072(7) 0.060(7) 0.034(5) -0.002(5) -0.001(5) -0.016(6)
C4 0.062(6) 0.047(6) 0.041(5) 0.004(4) -0.013(4) -0.001(5)
C2 0.083(8) 0.052(7) 0.044(6) 0.017(5) -0.022(5) -0.017(6)
C3 0.082(8) 0.049(8) 0.066(7) 0.005(6) -0.021(6) 0.007(6)
C9 0.066(7) 0.071(9) 0.048(6) -0.004(6) -0.017(5) -0.001(6)
C8 0.095(8) 0.060(7) 0.046(5) -0.020(5) -0.025(5) 0.022(7)
F3 0.072(5) 0.155(9) 0.094(6) -0.020(6) -0.014(4) 0.024(6)
C7 0.082(8) 0.044(6) 0.037(5) -0.004(4) -0.008(5) 0.018(5)
S1AA 0.0750(18) 0.064(2) 0.0546(14) 0.0049(14) -0.0069(12) -0.0056(17)

_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 C1 1.884(10) . ?
F1 C9 1.345(13) . ?
F2 C9 1.331(15) . ?
N2 C5 1.413(12) . ?
N1 C7 1.336(15) . ?
N1 C4 1.432(13) . ?
C5 C6 1.371(14) . ?
C5 C4 1.406(15) . ?
C6 C1 1.368(15) . ?
C1 C2 1.396(17) . ?
C4 C3 1.384(14) . ?
C2 C3 1.392(16) . ?
C9 F3 1.325(15) . ?
C9 C8 1.475(15) . ?
C8 C7 1.533(13) . ?
C7 S1AA 1.653(12) . ?

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
C7 N1 C4 123.1(10) . . ?
C6 C5 C4 117.3(10) . . ?
C6 C5 N2 121.1(10) . . ?
C4 C5 N2 121.5(10) . . ?
C1 C6 C5 121.9(12) . . ?
C6 C1 C2 120.5(10) . . ?
C6 C1 Br1 120.4(10) . . ?
C2 C1 Br1 119.0(8) . . ?
C3 C4 C5 122.2(11) . . ?
C3 C4 N1 118.1(11) . . ?
C5 C4 N1 119.7(9) . . ?
C3 C2 C1 119.4(9) . . ?
C4 C3 C2 118.7(12) . . ?
F3 C9 F2 105.4(12) . . ?
F3 C9 F1 106.3(10) . . ?
F2 C9 F1 106.2(10) . . ?
F3 C9 C8 113.1(11) . . ?
F2 C9 C8 114.2(11) . . ?
F1 C9 C8 111.1(11) . . ?
C9 C8 C7 112.1(10) . . ?
N1 C7 C8 113.2(11) . . ?
N1 C7 S1AA 124.9(8) . . ?
C8 C7 S1AA 121.9(10) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        71.25
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.123
