# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_test0_a
_database_code_depnum_ccdc_archive 'CCDC 1959494'
loop_
_audit_author_name
_audit_author_address
'Davi Fernando Back' 'Federal University of Santa Maria'
_audit_update_record             
;
2019-10-15 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;

_audit_creation_date             2019-10-15T14:59:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
1-(4-bromophenyl)-2-((tert-butylamino)methylene)-4,4,4-trifluorobutane-1,3-dione
;
_chemical_name_common            trifluoro-4-terc-butilamio-3-buten-2-ona
_chemical_formula_moiety         'C15 H15 Br F3 N O2'
_chemical_formula_sum            'C15 H15 Br F3 N O2'
_chemical_formula_weight         378.19
_chemical_melting_point          none
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  -P2ybc


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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                   16.298(10)
_cell_length_b                   8.588(6)
_cell_length_c                   12.152(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.311(17)
_cell_angle_gamma                90
_cell_volume                     1655.2(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1116
_cell_measurement_theta_min      2.697
_cell_measurement_theta_max      18.468

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.5932
_exptl_absorpt_correction_T_max  0.8736

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.1146
_diffrn_reflns_av_unetI/netI     0.2593
_diffrn_reflns_number            11802
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.7
_diffrn_reflns_theta_max         29.26
_diffrn_reflns_theta_full        29.26
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             4500
_reflns_number_gt                2034
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2008 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond (version 3.2i); Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0590P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         4500
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2237
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.1782
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_restrained_S_all      0.893
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Br51 Br 0.38155(5) 0.36948(11) 0.37029(7) 0.1228(5) Uani 1 1 d . . .
F42 F 0.8420(3) 0.2571(4) 0.0258(3) 0.0981(12) Uani 1 1 d . . .
F43 F 0.7901(3) 0.1267(4) 0.1439(3) 0.0961(12) Uani 1 1 d . . .
F41 F 0.9236(3) 0.1520(4) 0.1669(3) 0.1079(13) Uani 1 1 d . . .
O51 O 0.6815(3) 0.3670(5) 0.0643(3) 0.0893(15) Uani 1 1 d . . .
N1 N 0.8532(3) 0.6259(5) 0.3632(4) 0.0579(12) Uani 1 1 d . . .
H1 H 0.8999 0.5906 0.3516 0.069 Uiso 1 1 calc R . .
O31 O 0.9241(3) 0.4288(5) 0.2413(4) 0.0855(14) Uani 1 1 d . . .
C2 C 0.7778(4) 0.4340(6) 0.2296(4) 0.0516(15) Uani 1 1 d . . .
C51 C 0.6199(4) 0.3950(6) 0.2199(5) 0.0539(15) Uani 1 1 d . . .
C3 C 0.8530(4) 0.3765(7) 0.2066(4) 0.0582(16) Uani 1 1 d . . .
C1 C 0.7843(4) 0.5555(7) 0.3090(5) 0.0527(15) Uani 1 1 d . . .
H1A H 0.734 0.5897 0.3248 0.063 Uiso 1 1 calc R . .
C56 C 0.6260(4) 0.3487(6) 0.3302(5) 0.0625(16) Uani 1 1 d . . .
H56 H 0.6785 0.3224 0.3752 0.075 Uiso 1 1 calc R . .
C5 C 0.6913(4) 0.3945(7) 0.1639(5) 0.0615(16) Uani 1 1 d . . .
C11 C 0.8598(4) 0.7587(7) 0.4418(5) 0.0585(16) Uani 1 1 d . . .
C54 C 0.4780(4) 0.3829(7) 0.3099(6) 0.0687(17) Uani 1 1 d . . .
C55 C 0.5563(4) 0.3409(7) 0.3744(5) 0.0728(18) Uani 1 1 d . . .
H55 H 0.5616 0.3071 0.4485 0.087 Uiso 1 1 calc R . .
C4 C 0.8513(5) 0.2244(8) 0.1362(6) 0.0695(18) Uani 1 1 d . . .
C52 C 0.5415(4) 0.4332(7) 0.1570(5) 0.080(2) Uani 1 1 d . . .
H52 H 0.5361 0.4633 0.0822 0.096 Uiso 1 1 calc R . .
C53 C 0.4700(4) 0.4290(8) 0.1997(6) 0.089(2) Uani 1 1 d . . .
H53 H 0.4177 0.4567 0.1549 0.106 Uiso 1 1 calc R . .
C13 C 0.9363(5) 0.7263(8) 0.5383(6) 0.126(3) Uani 1 1 d . . .
H13A H 0.9857 0.7169 0.5084 0.189 Uiso 1 1 calc R . .
H13B H 0.9277 0.631 0.5754 0.189 Uiso 1 1 calc R . .
H13C H 0.9437 0.8104 0.5916 0.189 Uiso 1 1 calc R . .
C12 C 0.8794(5) 0.8999(7) 0.3794(6) 0.130(3) Uani 1 1 d . . .
H12A H 0.9297 0.8814 0.3529 0.195 Uiso 1 1 calc R . .
H12B H 0.8878 0.9881 0.4293 0.195 Uiso 1 1 calc R . .
H12C H 0.8333 0.9203 0.3161 0.195 Uiso 1 1 calc R . .
C14 C 0.7837(5) 0.7759(10) 0.4875(7) 0.146(4) Uani 1 1 d . . .
H14A H 0.7757 0.6832 0.5279 0.219 Uiso 1 1 calc R . .
H14B H 0.7354 0.7922 0.4264 0.219 Uiso 1 1 calc R . .
H14C H 0.7905 0.8636 0.5378 0.219 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Br51 C54 1.885(6) . ?
F42 C4 1.345(7) . ?
F43 C4 1.323(7) . ?
F41 C4 1.308(7) . ?
O51 C5 1.207(6) . ?
N1 C1 1.311(6) . ?
N1 C11 1.476(6) . ?
O31 C3 1.223(6) . ?
C2 C3 1.409(7) . ?
C2 C1 1.409(7) . ?
C2 C5 1.490(8) . ?
C51 C52 1.369(7) . ?
C51 C56 1.380(7) . ?
C51 C5 1.476(7) . ?
C3 C4 1.558(8) . ?
C56 C55 1.366(7) . ?
C11 C14 1.477(8) . ?
C11 C12 1.504(8) . ?
C11 C13 1.528(8) . ?
C54 C53 1.374(8) . ?
C54 C55 1.384(8) . ?
C52 C53 1.380(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 127.4(5) . . ?
C3 C2 C1 117.7(5) . . ?
C3 C2 C5 125.0(5) . . ?
C1 C2 C5 116.6(6) . . ?
C52 C51 C56 117.4(5) . . ?
C52 C51 C5 118.5(5) . . ?
C56 C51 C5 123.9(5) . . ?
O31 C3 C2 126.9(6) . . ?
O31 C3 C4 113.2(6) . . ?
C2 C3 C4 119.8(6) . . ?
N1 C1 C2 127.3(5) . . ?
C55 C56 C51 121.1(5) . . ?
O51 C5 C51 121.7(5) . . ?
O51 C5 C2 118.1(5) . . ?
C51 C5 C2 120.1(5) . . ?
N1 C11 C14 112.2(5) . . ?
N1 C11 C12 106.8(4) . . ?
C14 C11 C12 113.8(6) . . ?
N1 C11 C13 106.3(5) . . ?
C14 C11 C13 109.8(6) . . ?
C12 C11 C13 107.6(6) . . ?
C53 C54 C55 119.7(6) . . ?
C53 C54 Br51 119.8(6) . . ?
C55 C54 Br51 120.5(5) . . ?
C56 C55 C54 120.5(5) . . ?
F41 C4 F43 108.8(6) . . ?
F41 C4 F42 105.8(6) . . ?
F43 C4 F42 106.8(6) . . ?
F41 C4 C3 109.9(6) . . ?
F43 C4 C3 114.3(6) . . ?
F42 C4 C3 110.9(5) . . ?
C51 C52 C53 123.0(6) . . ?
C54 C53 C52 118.4(6) . . ?

# END of CIF
####################################################################### 
# 
# 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-1_a
_database_code_depnum_ccdc_archive 'CCDC 1959495'
loop_
_audit_author_name
_audit_author_address
'Davi Fernando Back' 'Federal University of Santa Maria'
_audit_update_record             
;
2019-10-15 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;

_audit_creation_date             2018-07-09T13:19:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
1-Phenyl-3-trifluormethyl-4-(methyl-(2-methoxyphenyl)imin)-5-(4-fluorphenyl)-1H-
;
_chemical_name_common            
'Phenyl trifluormethyl (methyl methoxyphenyl)imin fluorphenyl pyrazol'
_chemical_formula_moiety         'C24 H17 F4 N3 O'
_chemical_formula_sum            'C24 H17 F4 N3 O'
_chemical_formula_weight         439.41
_chemical_melting_point          none
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1



#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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

_cell_length_a                   9.0678(4)
_cell_length_b                   10.6289(5)
_cell_length_c                   11.4690(6)
_cell_angle_alpha                103.200(2)
_cell_angle_beta                 92.950(2)
_cell_angle_gamma                110.440(2)
_cell_volume                     997.94(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9721
_cell_measurement_theta_min      2.415
_cell_measurement_theta_max      29.172

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.9503
_exptl_absorpt_correction_T_max  0.9804

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_number            51922
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_full        29.19
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             5396
_reflns_number_gt                4849
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2008 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond (version 3.2i); Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0475P)²+0.4512P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         5396
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
F32 F 0.54381(7) 0.61754(7) 0.70451(6) 0.01923(14) Uani 1 1 d . . .
F33 F 0.36665(8) 0.70562(7) 0.74796(6) 0.02027(14) Uani 1 1 d . . .
F31 F 0.29960(8) 0.48335(7) 0.68951(6) 0.02283(15) Uani 1 1 d . . .
F51 F 0.58577(9) 0.88340(8) -0.01749(6) 0.02834(17) Uani 1 1 d . . .
O41 O 0.79231(9) 1.07832(8) 0.49881(7) 0.01834(16) Uani 1 1 d . . .
N1 N 0.24729(10) 0.54206(8) 0.36218(7) 0.01287(16) Uani 1 1 d . . .
N41 N 0.65406(10) 0.88584(8) 0.63574(8) 0.01390(16) Uani 1 1 d . . .
N2 N 0.23919(10) 0.50893(9) 0.47002(7) 0.01399(16) Uani 1 1 d . . .
C3 C 0.36582(11) 0.60684(10) 0.54209(9) 0.01244(17) Uani 1 1 d . . .
C51 C 0.42303(11) 0.71302(10) 0.26081(9) 0.01238(17) Uani 1 1 d . . .
C4 C 0.45824(11) 0.70333(10) 0.48271(8) 0.01209(17) Uani 1 1 d . . .
C5 C 0.37773(11) 0.65665(10) 0.36508(9) 0.01203(17) Uani 1 1 d . . .
C42 C 0.80608(11) 0.99409(10) 0.67130(9) 0.01286(18) Uani 1 1 d . . .
C43 C 0.88067(11) 1.08656(10) 0.60223(9) 0.01379(18) Uani 1 1 d . . .
C41 C 0.60995(11) 0.81967(10) 0.52402(9) 0.01281(18) Uani 1 1 d . . .
H41 H 0.6778 0.8471 0.4665 0.015 Uiso 1 1 calc R . .
C11 C 0.12342(11) 0.45808(10) 0.26338(9) 0.01335(18) Uani 1 1 d . . .
C56 C 0.47145(12) 0.85649(10) 0.27534(9) 0.01534(19) Uani 1 1 d . . .
H56 H 0.4682 0.9149 0.3506 0.018 Uiso 1 1 calc R . .
C52 C 0.42588(12) 0.62739(10) 0.14902(9) 0.01468(18) Uani 1 1 d . . .
H52 H 0.3904 0.5295 0.1376 0.018 Uiso 1 1 calc R . .
C16 C 0.04409(12) 0.52126(11) 0.20388(9) 0.01684(19) Uani 1 1 d . . .
H16 H 0.0715 0.6192 0.2281 0.02 Uiso 1 1 calc R . .
C12 C 0.08512(12) 0.31532(11) 0.22982(9) 0.01658(19) Uani 1 1 d . . .
H12 H 0.1404 0.2737 0.2715 0.02 Uiso 1 1 calc R . .
C53 C 0.48030(12) 0.68463(11) 0.05459(9) 0.0175(2) Uani 1 1 d . . .
H53 H 0.4834 0.6271 -0.0212 0.021 Uiso 1 1 calc R . .
C47 C 0.88390(12) 1.01129(10) 0.78521(9) 0.01616(19) Uani 1 1 d . . .
H47 H 0.831 0.9557 0.8357 0.019 Uiso 1 1 calc R . .
C54 C 0.52987(12) 0.82730(12) 0.07369(9) 0.0184(2) Uani 1 1 d . . .
C46 C 1.03783(13) 1.10853(11) 0.82636(10) 0.0191(2) Uani 1 1 d . . .
H46 H 1.0903 1.1174 0.9034 0.023 Uiso 1 1 calc R . .
C55 C 0.52433(13) 0.91485(11) 0.18099(10) 0.0185(2) Uani 1 1 d . . .
H55 H 0.5557 1.0121 0.1903 0.022 Uiso 1 1 calc R . .
C31 C 0.39379(11) 0.60371(10) 0.67068(9) 0.01428(18) Uani 1 1 d . . .
C45 C 1.11361(12) 1.19200(11) 0.75430(10) 0.0192(2) Uani 1 1 d . . .
H45 H 1.2201 1.2559 0.7806 0.023 Uiso 1 1 calc R . .
C15 C -0.07612(12) 0.43843(12) 0.10824(10) 0.0196(2) Uani 1 1 d . . .
H15 H -0.1319 0.48 0.0669 0.024 Uiso 1 1 calc R . .
C44 C 1.03499(12) 1.18310(10) 0.64338(10) 0.0169(2) Uani 1 1 d . . .
H44 H 1.0867 1.243 0.5956 0.02 Uiso 1 1 calc R . .
C14 C -0.11525(12) 0.29573(12) 0.07274(10) 0.0207(2) Uani 1 1 d . . .
H14 H -0.1964 0.24 0.0065 0.025 Uiso 1 1 calc R . .
C13 C -0.03579(13) 0.23424(11) 0.13402(10) 0.0201(2) Uani 1 1 d . . .
H13 H -0.0642 0.1362 0.1104 0.024 Uiso 1 1 calc R . .
C48 C 0.86820(14) 1.16725(12) 0.42557(10) 0.0220(2) Uani 1 1 d . . .
H48A H 0.7928 1.1517 0.3545 0.033 Uiso 1 1 calc R . .
H48B H 0.9602 1.1465 0.3992 0.033 Uiso 1 1 calc R . .
H48C H 0.9036 1.2646 0.4727 0.033 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
F32 C31 1.3426(11) . ?
F33 C31 1.3378(12) . ?
F31 C31 1.3397(11) . ?
F51 C54 1.3544(12) . ?
O41 C43 1.3646(12) . ?
O41 C48 1.4284(12) . ?
N1 N2 1.3599(11) . ?
N1 C5 1.3619(12) . ?
N1 C11 1.4315(12) . ?
N41 C41 1.2788(13) . ?
N41 C42 1.4179(12) . ?
N2 C3 1.3265(12) . ?
C3 C4 1.4126(13) . ?
C3 C31 1.4934(13) . ?
C51 C56 1.3981(13) . ?
C51 C52 1.3999(13) . ?
C51 C5 1.4709(13) . ?
C4 C5 1.3925(13) . ?
C4 C41 1.4572(13) . ?
C42 C47 1.3943(14) . ?
C42 C43 1.4133(13) . ?
C43 C44 1.3935(13) . ?
C11 C12 1.3866(14) . ?
C11 C16 1.3893(14) . ?
C56 C55 1.3921(14) . ?
C52 C53 1.3902(14) . ?
C16 C15 1.3900(14) . ?
C12 C13 1.3913(14) . ?
C53 C54 1.3826(15) . ?
C47 C46 1.3932(14) . ?
C54 C55 1.3780(15) . ?
C46 C45 1.3820(16) . ?
C45 C44 1.3928(15) . ?
C15 C14 1.3855(16) . ?
C14 C13 1.3881(16) . ?

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
C43 O41 C48 117.31(8) . . ?
N2 N1 C5 112.69(8) . . ?
N2 N1 C11 118.79(8) . . ?
C5 N1 C11 128.52(8) . . ?
C41 N41 C42 119.12(8) . . ?
C3 N2 N1 104.18(8) . . ?
N2 C3 C4 112.72(8) . . ?
N2 C3 C31 118.81(8) . . ?
C4 C3 C31 128.47(9) . . ?
C56 C51 C52 119.19(9) . . ?
C56 C51 C5 119.13(9) . . ?
C52 C51 C5 121.61(9) . . ?
C5 C4 C3 104.01(8) . . ?
C5 C4 C41 124.71(9) . . ?
C3 C4 C41 131.09(9) . . ?
N1 C5 C4 106.38(8) . . ?
N1 C5 C51 125.17(8) . . ?
C4 C5 C51 128.42(9) . . ?
C47 C42 C43 118.50(9) . . ?
C47 C42 N41 116.32(9) . . ?
C43 C42 N41 125.15(9) . . ?
O41 C43 C44 123.48(9) . . ?
O41 C43 C42 116.69(8) . . ?
C44 C43 C42 119.79(9) . . ?
N41 C41 C4 121.66(9) . . ?
C12 C11 C16 121.62(9) . . ?
C12 C11 N1 119.04(9) . . ?
C16 C11 N1 119.33(9) . . ?
C55 C56 C51 120.89(9) . . ?
C53 C52 C51 120.44(9) . . ?
C11 C16 C15 118.72(10) . . ?
C11 C12 C13 118.75(10) . . ?
C54 C53 C52 118.41(9) . . ?
C46 C47 C42 121.24(10) . . ?
F51 C54 C55 118.55(10) . . ?
F51 C54 C53 118.44(10) . . ?
C55 C54 C53 123.01(10) . . ?
C45 C46 C47 119.49(10) . . ?
C54 C55 C56 118.01(9) . . ?
F33 C31 F31 106.99(8) . . ?
F33 C31 F32 106.71(8) . . ?
F31 C31 F32 106.35(8) . . ?
F33 C31 C3 112.33(8) . . ?
F31 C31 C3 111.78(8) . . ?
F32 C31 C3 112.28(8) . . ?
C46 C45 C44 120.45(9) . . ?
C14 C15 C16 120.50(10) . . ?
C45 C44 C43 120.20(10) . . ?
C15 C14 C13 119.97(10) . . ?
C14 C13 C12 120.41(10) . . ?

# END of CIF
####################################################################### 
# 
# 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_dfbkibri_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1959496'
loop_
_audit_author_name
_audit_author_address
'Davi Fernando Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2019-10-15 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;

_audit_creation_date             2019-10-15T14:35:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
3-trifluormethyl-4-(2-methoxyphenyl)iminomethyl-5-(4-bromophenyl)-isoxal
;
_chemical_name_common            
'trifluormethyl methoxyphenyl iminomethyl bromophenyl isoxal'
_chemical_formula_moiety         'C18 H12 Br F3 N2 O2'
_chemical_formula_sum            'C18 H12 Br F3 N2 O2'
_chemical_formula_weight         425.21
_chemical_melting_point          none
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn



#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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                   12.889(2)
_cell_length_b                   5.2686(10)
_cell_length_c                   25.153(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.851(6)
_cell_angle_gamma                90
_cell_volume                     1692.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3977
_cell_measurement_theta_min      2.737
_cell_measurement_theta_max      26.751

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.5753
_exptl_absorpt_correction_T_max  0.7177

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_number            14746
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         27.2
_diffrn_reflns_theta_full        27.2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             3750
_reflns_number_gt                2246
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2008 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond (version 3.2i); Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0545P)²+0.8323P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3750
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Br51 Br 0.18041(3) 0.70048(10) 0.297832(18) 0.0869(2) Uani 1 1 d . . .
O41 O 0.63754(15) 1.1490(4) 0.32186(8) 0.0536(6) Uani 1 1 d . . .
O1 O 0.56875(18) 0.2176(4) 0.47664(10) 0.0601(6) Uani 1 1 d . . .
F31 F 0.87202(19) 0.5062(5) 0.54447(10) 0.0981(8) Uani 1 1 d . . .
N41 N 0.72155(19) 0.7907(5) 0.38713(11) 0.0524(7) Uani 1 1 d . . .
F32 F 0.90553(19) 0.2447(6) 0.48713(10) 0.1121(10) Uani 1 1 d . . .
C42 C 0.7899(2) 0.9589(5) 0.36532(11) 0.0397(7) Uani 1 1 d . . .
N2 N 0.6618(2) 0.1573(6) 0.50852(11) 0.0621(8) Uani 1 1 d . . .
C51 C 0.4886(2) 0.4849(6) 0.40777(11) 0.0432(7) Uani 1 1 d . . .
C43 C 0.7440(2) 1.1454(5) 0.33020(10) 0.0396(7) Uani 1 1 d . . .
F33 F 0.8505(2) 0.1196(6) 0.55816(12) 0.1308(12) Uani 1 1 d . . .
C4 C 0.6876(2) 0.4796(5) 0.45189(11) 0.0401(6) Uani 1 1 d . . .
C5 C 0.5837(2) 0.4113(6) 0.44272(11) 0.0433(7) Uani 1 1 d . . .
C47 C 0.8982(2) 0.9446(7) 0.37488(12) 0.0528(8) Uani 1 1 d . . .
H47 H 0.9295 0.8188 0.3976 0.063 Uiso 1 1 calc R . .
C41 C 0.7497(2) 0.6650(6) 0.42725(12) 0.0496(8) Uani 1 1 d . . .
H41 H 0.818 0.6904 0.4438 0.06 Uiso 1 1 calc R . .
C56 C 0.4840(2) 0.6991(6) 0.37583(13) 0.0502(8) Uani 1 1 d . . .
H56 H 0.5427 0.8023 0.3766 0.06 Uiso 1 1 calc R . .
C54 C 0.3063(2) 0.6087(7) 0.34232(13) 0.0542(8) Uani 1 1 d . . .
C46 C 0.9606(2) 1.1118(7) 0.35160(13) 0.0555(8) Uani 1 1 d . . .
H46 H 1.0332 1.0998 0.3587 0.067 Uiso 1 1 calc R . .
C55 C 0.3930(2) 0.7609(7) 0.34287(14) 0.0560(8) Uani 1 1 d . . .
H55 H 0.3904 0.9044 0.3212 0.067 Uiso 1 1 calc R . .
C44 C 0.8069(3) 1.3123(6) 0.30666(13) 0.0508(8) Uani 1 1 d . . .
H44 H 0.7766 1.4363 0.2832 0.061 Uiso 1 1 calc R . .
C45 C 0.9151(3) 1.2953(6) 0.31799(14) 0.0562(8) Uani 1 1 d . . .
H45 H 0.9569 1.4101 0.3025 0.067 Uiso 1 1 calc R . .
C3 C 0.7301(3) 0.3114(6) 0.49362(12) 0.0488(7) Uani 1 1 d . . .
C52 C 0.3992(3) 0.3359(6) 0.40680(14) 0.0578(9) Uani 1 1 d . . .
H52 H 0.4006 0.1934 0.4287 0.069 Uiso 1 1 calc R . .
C53 C 0.3085(3) 0.3978(7) 0.37360(15) 0.0639(9) Uani 1 1 d . . .
H53 H 0.2493 0.296 0.3726 0.077 Uiso 1 1 calc R . .
C48 C 0.5883(3) 1.3332(7) 0.28528(13) 0.0579(8) Uani 1 1 d . . .
H48A H 0.5136 1.3165 0.2828 0.087 Uiso 1 1 calc R . .
H48B H 0.6092 1.3068 0.2505 0.087 Uiso 1 1 calc R . .
H48C H 0.6087 1.5002 0.2978 0.087 Uiso 1 1 calc R . .
C31 C 0.8393(3) 0.2940(8) 0.52056(15) 0.0635(9) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Br51 C54 1.903(3) . ?
O41 C43 1.359(3) . ?
O41 C48 1.425(4) . ?
O1 C5 1.361(4) . ?
O1 N2 1.386(4) . ?
F31 C31 1.311(4) . ?
N41 C41 1.220(4) . ?
N41 C42 1.412(4) . ?
F32 C31 1.303(4) . ?
C42 C47 1.386(4) . ?
C42 C43 1.398(4) . ?
N2 C3 1.290(4) . ?
C51 C56 1.382(4) . ?
C51 C52 1.392(4) . ?
C51 C5 1.460(4) . ?
C43 C44 1.383(4) . ?
F33 C31 1.312(4) . ?
C4 C5 1.376(4) . ?
C4 C3 1.425(4) . ?
C4 C41 1.455(4) . ?
C47 C46 1.377(4) . ?
C56 C55 1.380(4) . ?
C54 C53 1.360(5) . ?
C54 C55 1.374(5) . ?
C46 C45 1.363(5) . ?
C44 C45 1.387(5) . ?
C3 C31 1.479(5) . ?
C52 C53 1.380(5) . ?

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
C43 O41 C48 117.4(2) . . ?
C5 O1 N2 110.5(2) . . ?
C41 N41 C42 122.1(3) . . ?
C47 C42 C43 118.5(3) . . ?
C47 C42 N41 124.4(3) . . ?
C43 C42 N41 117.0(2) . . ?
C3 N2 O1 105.0(2) . . ?
C56 C51 C52 118.8(3) . . ?
C56 C51 C5 122.2(3) . . ?
C52 C51 C5 119.0(3) . . ?
O41 C43 C44 124.3(3) . . ?
O41 C43 C42 116.0(2) . . ?
C44 C43 C42 119.7(3) . . ?
C5 C4 C3 103.2(3) . . ?
C5 C4 C41 133.2(3) . . ?
C3 C4 C41 123.6(3) . . ?
O1 C5 C4 108.0(3) . . ?
O1 C5 C51 113.5(3) . . ?
C4 C5 C51 138.5(3) . . ?
C46 C47 C42 121.6(3) . . ?
N41 C41 C4 126.7(3) . . ?
C55 C56 C51 120.5(3) . . ?
C53 C54 C55 121.2(3) . . ?
C53 C54 Br51 119.8(3) . . ?
C55 C54 Br51 119.0(3) . . ?
C45 C46 C47 119.4(3) . . ?
C54 C55 C56 119.5(3) . . ?
C43 C44 C45 120.2(3) . . ?
C46 C45 C44 120.6(3) . . ?
N2 C3 C4 113.3(3) . . ?
N2 C3 C31 118.2(3) . . ?
C4 C3 C31 128.5(3) . . ?
C53 C52 C51 120.5(3) . . ?
C54 C53 C52 119.5(3) . . ?
F32 C31 F31 105.6(3) . . ?
F32 C31 F33 108.0(3) . . ?
F31 C31 F33 105.6(3) . . ?
F32 C31 C3 112.5(3) . . ?
F31 C31 C3 112.5(3) . . ?
F33 C31 C3 112.2(3) . . ?

# END of CIF
