# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_DR-43-17
_database_code_depnum_ccdc_archive 'CCDC 1894204'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Dept. of Chemistry, Louisiana State University
United States of America
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2020-03-25 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         'C15 H14 Br F7 N2 O2'
_chemical_formula_sum            'C15 H14 Br F7 N2 O2'
_chemical_formula_weight         467.19

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.880(2)
_cell_length_b                   9.530(2)
_cell_length_c                   11.618(3)
_cell_angle_alpha                78.310(5)
_cell_angle_beta                 89.388(5)
_cell_angle_gamma                67.959(5)
_cell_volume                     890.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    4848
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      34.73
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    2.392
_shelx_estimated_absorpt_T_min   0.353
_shelx_estimated_absorpt_T_max   0.609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.326
_exptl_absorpt_correction_T_max  0.609
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12204
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.795
_diffrn_reflns_theta_max         35.041
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             7202
_reflns_number_gt                5646
_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 APEX3'
_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    ?
_computing_publication_material  ?
_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)+(0.0603P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7202
_refine_ls_number_parameters     253
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.33435(2) 0.31380(2) 0.95102(2) 0.02007(6) Uani 1 1 d . . . . .
F1 F 0.83872(16) -0.05801(12) 0.37464(11) 0.0224(2) Uani 1 1 d . . . . .
F2 F 0.98159(14) 0.08648(15) 0.36800(11) 0.0228(2) Uani 1 1 d . . . . .
F3 F 0.76683(19) 0.31042(13) 0.20362(11) 0.0314(3) Uani 1 1 d . . . . .
F4 F 0.59970(15) 0.18969(17) 0.22363(11) 0.0318(3) Uani 1 1 d . . . . .
F5 F 0.99902(19) 0.0466(3) 0.14088(15) 0.0521(5) Uani 1 1 d . . . . .
F6 F 0.8119(2) -0.04312(17) 0.13919(14) 0.0464(4) Uani 1 1 d . . . . .
F7 F 0.78077(19) 0.17371(16) 0.02787(11) 0.0338(3) Uani 1 1 d . . . . .
O1 O 0.30387(16) 0.21210(14) 0.42225(12) 0.0154(2) Uani 1 1 d . . . . .
O2 O 0.72830(17) 0.30229(14) 0.45333(12) 0.0175(3) Uani 1 1 d . . . . .
N1 N 0.36289(18) 0.39169(15) 0.49290(13) 0.0116(2) Uani 1 1 d D . . . .
H1N H 0.335(3) 0.4857(19) 0.489(2) 0.014 Uiso 1 1 d D U . . .
N2 N 0.64675(18) 0.09947(16) 0.51603(13) 0.0117(2) Uani 1 1 d D . . . .
H2N H 0.666(3) 0.0087(19) 0.513(2) 0.014 Uiso 1 1 d D U . . .
C1 C 0.43266(19) 0.29354(17) 0.60382(14) 0.0099(3) Uani 1 1 d . . . . .
C2 C 0.3663(2) 0.34177(18) 0.70515(15) 0.0117(3) Uani 1 1 d . . . . .
H2 H 0.2793 0.4394 0.6991 0.014 Uiso 1 1 calc R U . . .
C3 C 0.4279(2) 0.24646(19) 0.81450(15) 0.0137(3) Uani 1 1 d . . . . .
C4 C 0.5543(2) 0.10201(19) 0.82670(16) 0.0152(3) Uani 1 1 d . . . . .
H4 H 0.5929 0.0365 0.9023 0.018 Uiso 1 1 calc R U . . .
C5 C 0.6224(2) 0.05594(19) 0.72603(15) 0.0138(3) Uani 1 1 d . . . . .
H5 H 0.7094 -0.0419 0.7328 0.017 Uiso 1 1 calc R U . . .
C6 C 0.5649(2) 0.15154(18) 0.61477(15) 0.0110(3) Uani 1 1 d . . . . .
C7 C 0.29231(19) 0.34673(17) 0.41122(14) 0.0104(3) Uani 1 1 d . . . . .
C8 C 0.1951(2) 0.47504(18) 0.30602(15) 0.0118(3) Uani 1 1 d . . . . .
C9 C 0.3001(2) 0.5611(2) 0.24555(18) 0.0220(4) Uani 1 1 d . . . . .
H9A H 0.3982 0.4869 0.2203 0.033 Uiso 1 1 calc R U . . .
H9B H 0.3315 0.6119 0.3011 0.033 Uiso 1 1 calc R U . . .
H9C H 0.2376 0.6393 0.1767 0.033 Uiso 1 1 calc R U . . .
C10 C 0.1395(3) 0.4010(2) 0.21885(17) 0.0210(4) Uani 1 1 d . . . . .
H10A H 0.2349 0.3246 0.1928 0.032 Uiso 1 1 calc R U . . .
H10B H 0.0785 0.4813 0.1506 0.032 Uiso 1 1 calc R U . . .
H10C H 0.0695 0.3495 0.2572 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0458(2) 0.5902(2) 0.35064(18) 0.0213(4) Uani 1 1 d . . . . .
H11A H -0.0213 0.6686 0.2835 0.032 Uiso 1 1 calc R U . . .
H11B H 0.0817 0.6409 0.4040 0.032 Uiso 1 1 calc R U . . .
H11C H -0.0184 0.5347 0.3929 0.032 Uiso 1 1 calc R U . . .
C12 C 0.7269(2) 0.17553(18) 0.44888(15) 0.0119(3) Uani 1 1 d . . . . .
C13 C 0.8283(2) 0.09009(19) 0.35724(16) 0.0136(3) Uani 1 1 d . . . . .
C14 C 0.7581(2) 0.1704(2) 0.22949(16) 0.0149(3) Uani 1 1 d . . . . .
C15 C 0.8407(3) 0.0847(2) 0.13271(18) 0.0218(4) 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 C3 1.8979(18) . ?
F1 C13 1.3522(19) . ?
F2 C13 1.355(2) . ?
F3 C14 1.338(2) . ?
F4 C14 1.349(2) . ?
F5 C15 1.313(3) . ?
F6 C15 1.323(2) . ?
F7 C15 1.320(2) . ?
O1 C7 1.2280(19) . ?
O2 C12 1.224(2) . ?
N1 C7 1.362(2) . ?
N1 C1 1.419(2) . ?
N1 H1N 0.828(15) . ?
N2 C12 1.337(2) . ?
N2 C6 1.426(2) . ?
N2 H2N 0.825(15) . ?
C1 C2 1.395(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.383(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(2) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.536(2) . ?
C8 C10 1.526(2) . ?
C8 C11 1.535(3) . ?
C8 C9 1.537(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.545(2) . ?
C13 C14 1.542(2) . ?
C14 C15 1.541(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
C7 N1 C1 122.45(13) . . ?
C7 N1 H1N 118.0(16) . . ?
C1 N1 H1N 115.7(16) . . ?
C12 N2 C6 122.11(14) . . ?
C12 N2 H2N 118.8(17) . . ?
C6 N2 H2N 116.8(17) . . ?
C2 C1 C6 119.37(14) . . ?
C2 C1 N1 118.10(14) . . ?
C6 C1 N1 122.52(15) . . ?
C3 C2 C1 119.55(15) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.80(17) . . ?
C2 C3 Br1 118.78(13) . . ?
C4 C3 Br1 119.41(13) . . ?
C5 C4 C3 118.50(16) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 120.80(15) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.87(16) . . ?
C5 C6 N2 117.45(14) . . ?
C1 C6 N2 122.68(14) . . ?
O1 C7 N1 121.85(15) . . ?
O1 C7 C8 122.18(14) . . ?
N1 C7 C8 115.96(13) . . ?
C10 C8 C11 109.59(15) . . ?
C10 C8 C7 108.47(13) . . ?
C11 C8 C7 108.77(14) . . ?
C10 C8 C9 109.95(16) . . ?
C11 C8 C9 109.31(15) . . ?
C7 C8 C9 110.74(13) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 N2 127.11(17) . . ?
O2 C12 C13 118.10(15) . . ?
N2 C12 C13 114.79(14) . . ?
F1 C13 F2 107.69(14) . . ?
F1 C13 C14 107.53(14) . . ?
F2 C13 C14 108.24(14) . . ?
F1 C13 C12 112.02(14) . . ?
F2 C13 C12 108.55(14) . . ?
C14 C13 C12 112.62(14) . . ?
F3 C14 F4 108.32(15) . . ?
F3 C14 C15 107.21(16) . . ?
F4 C14 C15 107.83(15) . . ?
F3 C14 C13 109.31(14) . . ?
F4 C14 C13 107.58(15) . . ?
C15 C14 C13 116.35(15) . . ?
F5 C15 F7 108.99(19) . . ?
F5 C15 F6 108.3(2) . . ?
F7 C15 F6 107.02(17) . . ?
F5 C15 C14 111.45(16) . . ?
F7 C15 C14 109.76(16) . . ?
F6 C15 C14 111.15(17) . . ?

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
C7 N1 C1 C2 -118.27(18) . . . . ?
C7 N1 C1 C6 61.9(2) . . . . ?
C6 C1 C2 C3 -2.3(2) . . . . ?
N1 C1 C2 C3 177.86(15) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C2 C3 Br1 -179.46(12) . . . . ?
C2 C3 C4 C5 2.0(3) . . . . ?
Br1 C3 C4 C5 -179.11(13) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 -2.4(3) . . . . ?
C4 C5 C6 N2 176.87(15) . . . . ?
C2 C1 C6 C5 3.8(2) . . . . ?
N1 C1 C6 C5 -176.41(15) . . . . ?
C2 C1 C6 N2 -175.40(14) . . . . ?
N1 C1 C6 N2 4.4(2) . . . . ?
C12 N2 C6 C5 -115.91(18) . . . . ?
C12 N2 C6 C1 63.3(2) . . . . ?
C1 N1 C7 O1 -9.8(3) . . . . ?
C1 N1 C7 C8 169.09(15) . . . . ?
O1 C7 C8 C10 -6.5(2) . . . . ?
N1 C7 C8 C10 174.62(16) . . . . ?
O1 C7 C8 C11 112.65(18) . . . . ?
N1 C7 C8 C11 -66.25(19) . . . . ?
O1 C7 C8 C9 -127.21(18) . . . . ?
N1 C7 C8 C9 53.9(2) . . . . ?
C6 N2 C12 O2 -7.9(3) . . . . ?
C6 N2 C12 C13 171.63(14) . . . . ?
O2 C12 C13 F1 169.49(15) . . . . ?
N2 C12 C13 F1 -10.1(2) . . . . ?
O2 C12 C13 F2 50.7(2) . . . . ?
N2 C12 C13 F2 -128.90(15) . . . . ?
O2 C12 C13 C14 -69.1(2) . . . . ?
N2 C12 C13 C14 111.27(16) . . . . ?
F1 C13 C14 F3 -171.55(15) . . . . ?
F2 C13 C14 F3 -55.46(19) . . . . ?
C12 C13 C14 F3 64.55(19) . . . . ?
F1 C13 C14 F4 71.04(17) . . . . ?
F2 C13 C14 F4 -172.88(14) . . . . ?
C12 C13 C14 F4 -52.86(18) . . . . ?
F1 C13 C14 C15 -50.0(2) . . . . ?
F2 C13 C14 C15 66.10(19) . . . . ?
C12 C13 C14 C15 -173.89(15) . . . . ?
F3 C14 C15 F5 70.4(2) . . . . ?
F4 C14 C15 F5 -173.14(18) . . . . ?
C13 C14 C15 F5 -52.2(2) . . . . ?
F3 C14 C15 F7 -50.4(2) . . . . ?
F4 C14 C15 F7 66.0(2) . . . . ?
C13 C14 C15 F7 -173.08(16) . . . . ?
F3 C14 C15 F6 -168.61(17) . . . . ?
F4 C14 C15 F6 -52.2(2) . . . . ?
C13 C14 C15 F6 68.7(2) . . . . ?

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 H1N O2 0.828(15) 2.127(17) 2.9166(19) 159(2) 2_666
N2 H2N F1 0.825(15) 2.23(2) 2.6222(19) 109.6(19) .
N2 H2N O1 0.825(15) 2.002(17) 2.7731(19) 155(2) 2_656

_refine_diff_density_max         1.604
_refine_diff_density_min         -1.559
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_DR-42-39
_database_code_depnum_ccdc_archive 'CCDC 1894205'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Dept. of Chemistry, Louisiana State University
United States of America
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2020-03-25 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         'C10 H8 Br Cl F2 N2 O2'
_chemical_formula_sum            'C10 H8 Br Cl F2 N2 O2'
_chemical_formula_weight         341.54

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.038(3)
_cell_length_b                   17.636(6)
_cell_length_c                   8.445(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1197.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    6938
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      33.19
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.677
_shelx_estimated_absorpt_T_min   0.512
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29698
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.310
_diffrn_reflns_theta_max         33.312
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4519
_reflns_number_gt                3858
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.982

_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 APEX3'
_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    ?
_computing_publication_material  ?
_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)+(0.0187P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1594 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4519
_refine_ls_number_parameters     170
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0471
_refine_ls_wR_factor_gt          0.0457
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.95377(3) 0.22192(2) 0.03812(3) 0.01842(6) Uani 1 1 d . . . . .
Cl1 Cl 0.73814(12) 0.47962(6) 0.96058(9) 0.0621(3) Uani 1 1 d . . . . .
F1 F 0.5913(2) 0.56889(8) 0.7779(2) 0.0320(4) Uani 1 1 d . . . . .
F2 F 0.4752(2) 0.46175(10) 0.8062(2) 0.0369(4) Uani 1 1 d . . . . .
O1 O 0.85473(18) 0.17137(9) 0.63821(18) 0.0148(3) Uani 1 1 d . . . . .
O2 O 0.8399(2) 0.50531(10) 0.6027(2) 0.0234(4) Uani 1 1 d . . . . .
N1 N 0.6328(2) 0.24256(10) 0.57085(19) 0.0112(4) Uani 1 1 d D . . . .
H1N H 0.537(3) 0.2528(16) 0.590(3) 0.013 Uiso 1 1 d D U . . .
N2 N 0.6679(2) 0.40184(10) 0.5863(2) 0.0127(4) Uani 1 1 d D . . . .
H2N H 0.580(3) 0.3849(15) 0.623(3) 0.015 Uiso 1 1 d D U . . .
C1 C 0.7202(2) 0.28321(12) 0.4527(2) 0.0103(4) Uani 1 1 d . . . . .
C2 C 0.7840(3) 0.24244(12) 0.3259(3) 0.0119(4) Uani 1 1 d . . . . .
H2 H 0.7645 0.1895 0.3179 0.014 Uiso 1 1 calc R U . . .
C3 C 0.8760(3) 0.27934(13) 0.2117(2) 0.0133(4) Uani 1 1 d . . . . .
C4 C 0.9076(3) 0.35572(14) 0.2219(3) 0.0146(4) Uani 1 1 d . . . . .
H4 H 0.9758 0.3799 0.1452 0.018 Uiso 1 1 calc R U . . .
C5 C 0.8391(3) 0.39713(13) 0.3453(3) 0.0155(5) Uani 1 1 d . . . . .
H5 H 0.8575 0.4503 0.3511 0.019 Uiso 1 1 calc R U . . .
C6 C 0.7436(3) 0.36145(13) 0.4605(3) 0.0124(4) Uani 1 1 d . . . . .
C7 C 0.7039(3) 0.18513(12) 0.6508(3) 0.0111(4) Uani 1 1 d . . . . .
C8 C 0.5927(3) 0.13772(13) 0.7511(3) 0.0154(4) Uani 1 1 d . . . . .
H8A H 0.5712 0.0894 0.6977 0.023 Uiso 1 1 calc R U . . .
H8B H 0.4873 0.1644 0.7682 0.023 Uiso 1 1 calc R U . . .
H8C H 0.6464 0.1282 0.8533 0.023 Uiso 1 1 calc R U . . .
C9 C 0.7211(3) 0.46765(13) 0.6455(3) 0.0152(4) Uani 1 1 d . . . . .
C10 C 0.6227(3) 0.49559(12) 0.7897(3) 0.0158(4) 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 C3 1.888(2) . ?
Cl1 C10 1.739(2) . ?
F1 C10 1.321(3) . ?
F2 C10 1.335(3) . ?
O1 C7 1.241(2) . ?
O2 C9 1.218(3) . ?
N1 C7 1.345(3) . ?
N1 C1 1.415(3) . ?
N1 H1N 0.81(2) . ?
N2 C9 1.334(3) . ?
N2 C6 1.416(3) . ?
N2 H2N 0.827(19) . ?
C1 C2 1.388(3) . ?
C1 C6 1.394(3) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(3) . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.488(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.533(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
C7 N1 C1 121.64(18) . . ?
C7 N1 H1N 118(2) . . ?
C1 N1 H1N 120(2) . . ?
C9 N2 C6 125.5(2) . . ?
C9 N2 H2N 116.5(19) . . ?
C6 N2 H2N 117.9(19) . . ?
C2 C1 C6 120.0(2) . . ?
C2 C1 N1 117.72(19) . . ?
C6 C1 N1 122.32(19) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 Br1 120.90(17) . . ?
C2 C3 Br1 117.87(16) . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 N2 122.3(2) . . ?
C1 C6 N2 118.40(19) . . ?
O1 C7 N1 121.3(2) . . ?
O1 C7 C8 121.7(2) . . ?
N1 C7 C8 116.97(19) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 N2 127.9(2) . . ?
O2 C9 C10 117.7(2) . . ?
N2 C9 C10 114.3(2) . . ?
F1 C10 F2 106.0(2) . . ?
F1 C10 C9 110.70(19) . . ?
F2 C10 C9 113.43(18) . . ?
F1 C10 Cl1 108.84(16) . . ?
F2 C10 Cl1 108.37(17) . . ?
C9 C10 Cl1 109.36(16) . . ?

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
C7 N1 C1 C2 57.6(3) . . . . ?
C7 N1 C1 C6 -122.2(2) . . . . ?
C6 C1 C2 C3 2.6(3) . . . . ?
N1 C1 C2 C3 -177.2(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 Br1 -177.95(16) . . . . ?
C2 C3 C4 C5 -3.1(3) . . . . ?
Br1 C3 C4 C5 175.62(17) . . . . ?
C3 C4 C5 C6 2.0(3) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C5 C6 N2 -178.4(2) . . . . ?
C2 C1 C6 C5 -3.6(3) . . . . ?
N1 C1 C6 C5 176.2(2) . . . . ?
C2 C1 C6 N2 176.11(19) . . . . ?
N1 C1 C6 N2 -4.1(3) . . . . ?
C9 N2 C6 C5 -25.9(3) . . . . ?
C9 N2 C6 C1 154.4(2) . . . . ?
C1 N1 C7 O1 8.9(3) . . . . ?
C1 N1 C7 C8 -169.41(18) . . . . ?
C6 N2 C9 O2 1.3(4) . . . . ?
C6 N2 C9 C10 -175.64(19) . . . . ?
O2 C9 C10 F1 46.5(3) . . . . ?
N2 C9 C10 F1 -136.3(2) . . . . ?
O2 C9 C10 F2 165.5(2) . . . . ?
N2 C9 C10 F2 -17.3(3) . . . . ?
O2 C9 C10 Cl1 -73.5(2) . . . . ?
N2 C9 C10 Cl1 103.8(2) . . . . ?

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 H1N O1 0.81(2) 2.02(2) 2.761(2) 151(3) 4_455
N2 H2N F2 0.827(19) 2.22(3) 2.639(3) 111(2) .
N2 H2N O1 0.827(19) 2.07(2) 2.863(3) 160(3) 4_455

_refine_diff_density_max         0.707
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_DL-13-80-2
_database_code_depnum_ccdc_archive 'CCDC 1953041'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Department of Chemistry  Louisiana State University
United States of America
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-03-25 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         'C10 H7 Br2 F3 N2 O2'
_chemical_formula_sum            'C10 H7 Br2 F3 N2 O2'
_chemical_formula_weight         404.00

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   14.7917(11)
_cell_length_b                   4.5444(3)
_cell_length_c                   18.3744(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.065(3)
_cell_angle_gamma                90
_cell_volume                     1235.12(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9126
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      32.90
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.173
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    6.600
_shelx_estimated_absorpt_T_min   0.155
_shelx_estimated_absorpt_T_max   0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_T_max  0.778
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33678
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.766
_diffrn_reflns_theta_max         33.209
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8104
_reflns_number_gt                7660
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    1.000

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component pseudomerohedral twin. The
BASF parameter refined to 0.1073(10).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.1932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2638 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8104
_refine_ls_number_parameters     419
_refine_ls_number_restraints     92
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0552
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.71049(3) 1.16033(11) 0.49751(2) 0.02535(10) Uani 1 1 d . . . . .
Br2 Br 0.91532(3) 1.46272(9) 0.46230(2) 0.02104(9) Uani 1 1 d . . . . .
F1 F 0.55401(17) 0.2709(8) 0.17175(16) 0.0275(7) Uani 0.882(4) 1 d D . P A 1
F2 F 0.63754(19) 0.5567(7) 0.10832(13) 0.0239(6) Uani 0.882(4) 1 d D . P A 1
F3 F 0.69445(17) 0.1670(7) 0.15693(14) 0.0197(6) Uani 0.882(4) 1 d D . P A 1
F1A F 0.9281(11) 0.809(5) 0.0496(9) 0.018(4) Uani 0.118(4) 1 d D U P A 2
F2A F 1.0172(12) 1.171(4) 0.0727(10) 0.018(4) Uani 0.118(4) 1 d D U P A 2
F3A F 1.0436(11) 0.758(5) 0.1232(10) 0.018(4) Uani 0.118(4) 1 d D U P A 2
O1 O 0.59378(19) 0.6823(10) 0.26651(16) 0.0332(9) Uani 1 1 d . . . . .
O2 O 0.88344(16) 1.2869(7) 0.16254(14) 0.0173(5) Uani 1 1 d . . . . .
N1 N 0.74527(19) 0.6034(7) 0.24782(16) 0.0146(6) Uani 1 1 d D . . . .
H1N H 0.782(3) 0.521(11) 0.219(2) 0.017 Uiso 1 1 d D U . . .
N2 N 0.9150(2) 0.8586(9) 0.22024(17) 0.0170(6) Uani 1 1 d D . . . .
H2N H 0.936(3) 0.687(7) 0.218(3) 0.020 Uiso 1 1 d D U . . .
C1 C 0.7744(2) 1.0767(9) 0.41118(18) 0.0168(7) Uani 1 1 d . . . . .
C2 C 0.8574(3) 1.2016(9) 0.39697(19) 0.0176(7) Uani 1 1 d . . . . .
C3 C 0.9033(3) 1.1294(10) 0.3333(2) 0.0172(7) Uani 1 1 d . . . . .
H3 H 0.9603 1.2165 0.3232 0.021 Uiso 1 1 calc R U . . .
C4 C 0.8660(2) 0.9316(9) 0.28493(19) 0.0156(7) Uani 1 1 d . . . . .
C5 C 0.7819(2) 0.8034(9) 0.29885(18) 0.0146(7) Uani 1 1 d . . . . .
C6 C 0.7361(2) 0.8753(9) 0.36278(18) 0.0162(7) Uani 1 1 d . . . . .
H6 H 0.6792 0.7879 0.3733 0.019 Uiso 1 1 calc R U . . .
C7 C 0.6565(2) 0.5679(10) 0.23431(19) 0.0182(8) Uani 1 1 d . . . . .
C8 C 0.6364(2) 0.3787(10) 0.16713(19) 0.0181(8) Uani 1 1 d D . . . .
H8A H 0.5970 0.2144 0.1809 0.027 Uiso 0.118(4) 1 calc R U P A 2
H8B H 0.6931 0.3018 0.1473 0.027 Uiso 0.118(4) 1 calc R U P A 2
H8C H 0.6060 0.4990 0.1302 0.027 Uiso 0.118(4) 1 calc R U P A 2
C9 C 0.9206(2) 1.0467(10) 0.16336(18) 0.0131(6) Uani 1 1 d . . . . .
C10 C 0.9750(2) 0.9337(10) 0.1002(2) 0.0176(7) Uani 1 1 d D . . . .
H10A H 0.9352 0.8289 0.0664 0.026 Uiso 0.882(4) 1 calc R U P A 1
H10B H 1.0218 0.7992 0.1181 0.026 Uiso 0.882(4) 1 calc R U P A 1
H10C H 1.0036 1.0995 0.0751 0.026 Uiso 0.882(4) 1 calc R U P A 1
Br3 Br 0.19718(2) -0.16547(11) 0.00276(2) 0.02210(9) Uani 1 1 d . . . . .
Br4 Br 0.40361(2) -0.46265(8) 0.03391(2) 0.01769(8) Uani 1 1 d . . . . .
F4 F 0.0568(4) 0.7579(16) 0.3264(4) 0.0308(16) Uani 0.433(4) 1 d D . P B 1
F5 F 0.1982(3) 0.8369(15) 0.3421(3) 0.0210(12) Uani 0.433(4) 1 d D . P B 1
F6 F 0.1351(4) 0.4528(15) 0.3877(3) 0.0265(14) Uani 0.433(4) 1 d D . P B 1
F4A F 0.5412(3) 0.2459(11) 0.3691(2) 0.0215(10) Uani 0.567(4) 1 d D . P B 2
F5A F 0.4298(3) 0.1885(14) 0.4431(2) 0.0251(11) Uani 0.567(4) 1 d D . P B 2
F6A F 0.5197(3) -0.1744(10) 0.4214(2) 0.0202(9) Uani 0.567(4) 1 d D . P B 2
O3 O 0.08758(18) 0.3807(9) 0.22666(16) 0.0281(8) Uani 1 1 d . . . . .
O4 O 0.3788(2) -0.2869(7) 0.33512(15) 0.0235(7) Uani 1 1 d . . . . .
N3 N 0.23959(19) 0.3994(8) 0.25091(16) 0.0148(6) Uani 1 1 d D . . . .
H3N H 0.276(3) 0.470(11) 0.280(2) 0.018 Uiso 1 1 d D U . . .
N4 N 0.4084(2) 0.1383(9) 0.27635(16) 0.0165(6) Uani 1 1 d D . . . .
H4N H 0.438(3) 0.293(8) 0.274(3) 0.020 Uiso 1 1 d D U . . .
C11 C 0.2633(2) -0.0804(9) 0.08802(18) 0.0166(7) Uani 1 1 d . . . . .
C12 C 0.3475(2) -0.2048(9) 0.10019(18) 0.0148(7) Uani 1 1 d . . . . .
C13 C 0.3942(2) -0.1304(10) 0.16334(18) 0.0157(7) Uani 1 1 d . . . . .
H13 H 0.4516 -0.2162 0.1729 0.019 Uiso 1 1 calc R U . . .
C14 C 0.3576(2) 0.0682(9) 0.21253(19) 0.0155(7) Uani 1 1 d . . . . .
C15 C 0.2731(2) 0.1952(9) 0.19991(18) 0.0140(7) Uani 1 1 d . . . . .
C16 C 0.2257(2) 0.1190(9) 0.13695(18) 0.0156(7) Uani 1 1 d . . . . .
H16 H 0.1680 0.2027 0.1275 0.019 Uiso 1 1 calc R U . . .
C17 C 0.1510(2) 0.4737(11) 0.26173(19) 0.0196(8) Uani 1 1 d D . . . .
C18 C 0.1366(10) 0.639(3) 0.3328(5) 0.023(2) Uani 0.433(4) 1 d D . P B 1
C18A C 0.1358(9) 0.701(3) 0.3214(5) 0.023(2) Uani 0.567(4) 1 d D . P B 2
H18A H 0.1018 0.8679 0.3015 0.034 Uiso 0.567(4) 1 calc R U P B 2
H18B H 0.1943 0.7699 0.3397 0.034 Uiso 0.567(4) 1 calc R U P B 2
H18C H 0.1015 0.6115 0.3612 0.034 Uiso 0.567(4) 1 calc R U P B 2
C19 C 0.4164(2) -0.0487(10) 0.33171(18) 0.0136(7) Uani 1 1 d . . . . .
C20 C 0.4767(2) 0.0562(9) 0.39400(18) 0.0160(7) Uani 1 1 d D . . . .
H20A H 0.4396 0.1532 0.4311 0.024 Uiso 0.433(4) 1 calc R U P B 1
H20B H 0.5216 0.1956 0.3752 0.024 Uiso 0.433(4) 1 calc R U P B 1
H20C H 0.5078 -0.1130 0.4157 0.024 Uiso 0.433(4) 1 calc R U P B 1


_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 1.886(3) . ?
Br2 C2 1.893(4) . ?
F1 C8 1.316(4) . ?
F2 C8 1.350(5) . ?
F3 C8 1.304(5) . ?
F1A C10 1.293(13) . ?
F2A C10 1.344(14) . ?
F3A C10 1.356(13) . ?
O1 C7 1.217(5) . ?
O2 C9 1.222(5) . ?
N1 C7 1.346(5) . ?
N1 C5 1.414(5) . ?
N1 H1N 0.84(3) . ?
N2 C9 1.353(5) . ?
N2 C4 1.432(4) . ?
N2 H2N 0.84(3) . ?
C1 C2 1.378(6) . ?
C1 C6 1.396(5) . ?
C2 C3 1.392(5) . ?
C3 C4 1.379(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(5) . ?
C5 C6 1.396(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.533(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.503(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
Br3 C11 1.886(3) . ?
Br4 C12 1.883(4) . ?
F4 C18 1.303(15) . ?
F5 C18 1.293(14) . ?
F6 C18 1.317(14) . ?
F4A C20 1.365(5) . ?
F5A C20 1.287(5) . ?
F6A C20 1.324(6) . ?
O3 C17 1.214(4) . ?
O4 C19 1.219(5) . ?
N3 C17 1.367(5) . ?
N3 C15 1.409(5) . ?
N3 H3N 0.83(3) . ?
N4 C19 1.330(5) . ?
N4 C14 1.427(4) . ?
N4 H4N 0.83(3) . ?
C11 C12 1.385(5) . ?
C11 C16 1.393(5) . ?
C12 C13 1.391(5) . ?
C13 C14 1.387(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(5) . ?
C15 C16 1.396(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.521(7) . ?
C17 C18A 1.523(7) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19 C20 1.527(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C7 N1 C5 124.9(3) . . ?
C7 N1 H1N 117(3) . . ?
C5 N1 H1N 117(3) . . ?
C9 N2 C4 121.8(4) . . ?
C9 N2 H2N 122(3) . . ?
C4 N2 H2N 116(3) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 Br1 121.6(3) . . ?
C6 C1 Br1 117.7(3) . . ?
C1 C2 C3 119.9(4) . . ?
C1 C2 Br2 122.8(3) . . ?
C3 C2 Br2 117.3(3) . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 N2 118.9(3) . . ?
C5 C4 N2 120.5(3) . . ?
C6 C5 C4 119.3(4) . . ?
C6 C5 N1 121.5(3) . . ?
C4 C5 N1 119.2(3) . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O1 C7 N1 127.1(4) . . ?
O1 C7 C8 118.9(3) . . ?
N1 C7 C8 113.8(3) . . ?
F3 C8 F1 110.2(4) . . ?
F3 C8 F2 108.5(3) . . ?
F1 C8 F2 106.7(3) . . ?
F3 C8 C7 113.7(3) . . ?
F1 C8 C7 109.6(3) . . ?
F2 C8 C7 107.8(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 N2 123.1(3) . . ?
O2 C9 C10 122.5(3) . . ?
N2 C9 C10 114.4(4) . . ?
F1A C10 F2A 109.3(12) . . ?
F1A C10 F3A 111.5(14) . . ?
F2A C10 F3A 104.0(12) . . ?
F1A C10 C9 114.7(8) . . ?
F2A C10 C9 105.4(9) . . ?
F3A C10 C9 111.2(8) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C17 N3 C15 126.6(3) . . ?
C17 N3 H3N 116(3) . . ?
C15 N3 H3N 117(3) . . ?
C19 N4 C14 122.1(4) . . ?
C19 N4 H4N 123(3) . . ?
C14 N4 H4N 115(3) . . ?
C12 C11 C16 121.4(3) . . ?
C12 C11 Br3 121.0(3) . . ?
C16 C11 Br3 117.5(3) . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 Br4 123.1(3) . . ?
C13 C12 Br4 118.2(3) . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 N4 118.4(3) . . ?
C15 C14 N4 120.9(3) . . ?
C16 C15 C14 119.0(3) . . ?
C16 C15 N3 122.5(3) . . ?
C14 C15 N3 118.5(3) . . ?
C11 C16 C15 119.7(3) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
O3 C17 N3 125.3(4) . . ?
O3 C17 C18 121.2(7) . . ?
N3 C17 C18 112.5(6) . . ?
O3 C17 C18A 120.2(6) . . ?
N3 C17 C18A 114.5(6) . . ?
F5 C18 F4 111.1(10) . . ?
F5 C18 F6 110.9(10) . . ?
F4 C18 F6 108.7(11) . . ?
F5 C18 C17 110.9(9) . . ?
F4 C18 C17 104.9(9) . . ?
F6 C18 C17 110.1(8) . . ?
C17 C18A H18A 109.5 . . ?
C17 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
O4 C19 N4 124.5(3) . . ?
O4 C19 C20 120.3(3) . . ?
N4 C19 C20 115.2(4) . . ?
F5A C20 F6A 111.2(4) . . ?
F5A C20 F4A 108.4(4) . . ?
F6A C20 F4A 107.0(3) . . ?
F5A C20 C19 110.8(3) . . ?
F6A C20 C19 108.5(4) . . ?
F4A C20 C19 110.8(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C6 C1 C2 C3 0.8(6) . . . . ?
Br1 C1 C2 C3 178.6(3) . . . . ?
C6 C1 C2 Br2 -177.2(3) . . . . ?
Br1 C1 C2 Br2 0.7(5) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
Br2 C2 C3 C4 177.5(3) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C2 C3 C4 N2 -179.3(4) . . . . ?
C9 N2 C4 C3 -75.0(5) . . . . ?
C9 N2 C4 C5 105.3(5) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
N2 C4 C5 C6 179.2(4) . . . . ?
C3 C4 C5 N1 179.4(4) . . . . ?
N2 C4 C5 N1 -0.8(6) . . . . ?
C7 N1 C5 C6 32.3(6) . . . . ?
C7 N1 C5 C4 -147.7(4) . . . . ?
C2 C1 C6 C5 -0.9(6) . . . . ?
Br1 C1 C6 C5 -178.9(3) . . . . ?
C4 C5 C6 C1 0.8(6) . . . . ?
N1 C5 C6 C1 -179.2(3) . . . . ?
C5 N1 C7 O1 -5.8(7) . . . . ?
C5 N1 C7 C8 169.4(3) . . . . ?
O1 C7 C8 F3 -149.9(4) . . . . ?
N1 C7 C8 F3 34.4(5) . . . . ?
O1 C7 C8 F1 -26.1(6) . . . . ?
N1 C7 C8 F1 158.2(4) . . . . ?
O1 C7 C8 F2 89.7(5) . . . . ?
N1 C7 C8 F2 -86.0(4) . . . . ?
C4 N2 C9 O2 -1.3(5) . . . . ?
C4 N2 C9 C10 179.8(3) . . . . ?
O2 C9 C10 F1A -83.9(13) . . . . ?
N2 C9 C10 F1A 95.0(13) . . . . ?
O2 C9 C10 F2A 36.4(10) . . . . ?
N2 C9 C10 F2A -144.7(10) . . . . ?
O2 C9 C10 F3A 148.5(11) . . . . ?
N2 C9 C10 F3A -32.7(12) . . . . ?
C16 C11 C12 C13 0.9(6) . . . . ?
Br3 C11 C12 C13 178.8(3) . . . . ?
C16 C11 C12 Br4 -177.3(3) . . . . ?
Br3 C11 C12 Br4 0.6(5) . . . . ?
C11 C12 C13 C14 -1.0(6) . . . . ?
Br4 C12 C13 C14 177.3(3) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C12 C13 C14 N4 -179.7(4) . . . . ?
C19 N4 C14 C13 -74.1(5) . . . . ?
C19 N4 C14 C15 105.7(5) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
N4 C14 C15 C16 -179.7(4) . . . . ?
C13 C14 C15 N3 -178.9(4) . . . . ?
N4 C14 C15 N3 1.3(6) . . . . ?
C17 N3 C15 C16 23.6(6) . . . . ?
C17 N3 C15 C14 -157.4(4) . . . . ?
C12 C11 C16 C15 -0.3(6) . . . . ?
Br3 C11 C16 C15 -178.3(3) . . . . ?
C14 C15 C16 C11 -0.2(6) . . . . ?
N3 C15 C16 C11 178.8(3) . . . . ?
C15 N3 C17 O3 -2.8(7) . . . . ?
C15 N3 C17 C18 165.3(7) . . . . ?
C15 N3 C17 C18A 179.7(6) . . . . ?
O3 C17 C18 F5 -147.4(8) . . . . ?
N3 C17 C18 F5 44.0(12) . . . . ?
O3 C17 C18 F4 -27.3(13) . . . . ?
N3 C17 C18 F4 164.1(8) . . . . ?
O3 C17 C18 F6 89.5(11) . . . . ?
N3 C17 C18 F6 -79.2(11) . . . . ?
C14 N4 C19 O4 -3.6(6) . . . . ?
C14 N4 C19 C20 177.2(3) . . . . ?
O4 C19 C20 F5A -86.7(5) . . . . ?
N4 C19 C20 F5A 92.6(5) . . . . ?
O4 C19 C20 F6A 35.8(5) . . . . ?
N4 C19 C20 F6A -145.0(4) . . . . ?
O4 C19 C20 F4A 152.9(4) . . . . ?
N4 C19 C20 F4A -27.8(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 H1N O2 0.84(3) 2.12(3) 2.951(4) 171(4) 1_545
N2 H2N O2 0.84(3) 2.23(4) 2.845(5) 130(4) 1_545
N2 H2N O3 0.84(3) 2.64(3) 3.354(5) 144(4) 1_655
N3 H3N O4 0.83(3) 2.13(3) 2.942(4) 167(5) 1_565
N4 H4N F1 0.83(3) 2.54(5) 2.951(4) 112(4) .
N4 H4N O4 0.83(3) 2.39(5) 2.861(5) 117(4) 1_565

_refine_diff_density_max         0.820
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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_DR-43-53
_database_code_depnum_ccdc_archive 'CCDC 1894208'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Dept. of Chemistry, Louisiana State University
United States of America
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2020-03-25 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         'C15 H10 Br F3 N2 O2'
_chemical_formula_sum            'C15 H10 Br F3 N2 O2'
_chemical_formula_weight         387.16

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'
Br Br -0.2901 2.4595 '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                   4.7893(2)
_cell_length_b                   15.1129(6)
_cell_length_c                   20.3712(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.856(3)
_cell_angle_gamma                90
_cell_volume                     1473.70(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    3419
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      26.83
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.833
_shelx_estimated_absorpt_T_min   0.446
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17123
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.678
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4466
_reflns_number_gt                3057
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0579P)²+1.3213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4466
_refine_ls_number_parameters     224
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.031
_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
Br1 Br 0.06860(8) 0.60330(3) 0.44128(2) 0.02316(13) Uani 0.9544(18) 1 d . . P A
1
Br1A Br 0.393(2) 0.3855(7) 0.4653(4) 0.031(3) Uani 0.0456(18) 1 d . U P A 2
F1 F 1.2195(5) 0.22665(17) 0.20882(14) 0.0365(6) Uani 1 1 d . . . . .
F2 F 0.9610(5) 0.30476(19) 0.14318(12) 0.0360(6) Uani 1 1 d . . . . .
F3 F 1.3183(5) 0.36316(16) 0.19200(12) 0.0285(5) Uani 1 1 d . . . . .
O1 O 0.1244(5) 0.54787(18) 0.18284(12) 0.0198(5) Uani 1 1 d . . . . .
O2 O 0.8080(6) 0.27062(19) 0.28656(14) 0.0305(7) Uani 1 1 d . . . . .
N1 N 0.5749(6) 0.5671(2) 0.21736(14) 0.0151(6) Uani 1 1 d D . . . .
H1N H 0.746(5) 0.575(3) 0.2034(19) 0.018 Uiso 1 1 d D U . . .
N2 N 0.8749(6) 0.4176(2) 0.26169(15) 0.0172(6) Uani 1 1 d D . . . .
H2N H 0.965(8) 0.453(2) 0.2356(17) 0.021 Uiso 1 1 d D U . . .
C1 C 0.5347(7) 0.5327(2) 0.28176(17) 0.0164(7) Uani 1 1 d . . . . .
C2 C 0.3524(7) 0.5757(2) 0.32260(17) 0.0172(7) Uani 1 1 d . . . . .
H2 H 0.2598 0.6282 0.3083 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3061(7) 0.5413(3) 0.38461(17) 0.0189(7) Uani 1 1 d . . . . .
H3 H 0.1819 0.5707 0.4127 0.023 Uiso 0.0456(18) 1 calc R U P A 2
C4 C 0.4392(8) 0.4644(3) 0.40592(18) 0.0225(8) Uani 1 1 d . . . . .
H4 H 0.4024 0.4404 0.4479 0.027 Uiso 0.9544(18) 1 calc R U P A 1
C5 C 0.6261(8) 0.4231(3) 0.36554(18) 0.0216(8) Uani 1 1 d . . . . .
H5 H 0.7203 0.3712 0.3803 0.026 Uiso 1 1 calc R U . . .
C6 C 0.6771(7) 0.4570(2) 0.30367(17) 0.0169(7) Uani 1 1 d . . . . .
C7 C 0.3626(7) 0.5748(2) 0.17232(17) 0.0153(7) Uani 1 1 d . . . . .
C8 C 0.4337(7) 0.6151(3) 0.10881(18) 0.0194(7) Uani 1 1 d . . . . .
C9 C 0.6345(9) 0.6811(3) 0.1044(2) 0.0309(9) Uani 1 1 d . . . . .
H9 H 0.7335 0.7009 0.1428 0.037 Uiso 1 1 calc R U . . .
C10 C 0.6908(11) 0.7185(4) 0.0434(2) 0.0397(11) Uani 1 1 d . . . . .
H10 H 0.8276 0.7637 0.0404 0.048 Uiso 1 1 calc R U . . .
C11 C 0.5480(10) 0.6897(4) -0.0121(2) 0.0406(12) Uani 1 1 d . . . . .
H11 H 0.5848 0.7154 -0.0535 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3502(12) 0.6231(4) -0.0080(2) 0.0486(14) Uani 1 1 d . . . . .
H12 H 0.2565 0.6021 -0.0467 0.058 Uiso 1 1 calc R U . . .
C13 C 0.2881(10) 0.5868(4) 0.0526(2) 0.0390(12) Uani 1 1 d . . . . .
H13 H 0.1470 0.5429 0.0555 0.047 Uiso 1 1 calc R U . . .
C14 C 0.9141(8) 0.3302(3) 0.25562(18) 0.0204(7) Uani 1 1 d . . . . .
C15 C 1.1085(7) 0.3060(2) 0.20014(19) 0.0195(7) 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 C3 1.895(4) . ?
Br1A C4 1.718(10) . ?
F1 C15 1.321(4) . ?
F2 C15 1.339(4) . ?
F3 C15 1.340(4) . ?
O1 C7 1.236(4) . ?
O2 C14 1.220(5) . ?
N1 C7 1.352(4) . ?
N1 C1 1.430(4) . ?
N1 H1N 0.885(19) . ?
N2 C14 1.340(5) . ?
N2 C6 1.427(5) . ?
N2 H2N 0.881(19) . ?
C1 C2 1.387(5) . ?
C1 C6 1.398(5) . ?
C2 C3 1.390(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(5) . ?
C5 H5 0.9500 . ?
C7 C8 1.479(5) . ?
C8 C13 1.388(6) . ?
C8 C9 1.392(6) . ?
C9 C10 1.398(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.532(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
C7 N1 C1 122.2(3) . . ?
C7 N1 H1N 117(3) . . ?
C1 N1 H1N 120(3) . . ?
C14 N2 C6 124.4(3) . . ?
C14 N2 H2N 118(3) . . ?
C6 N2 H2N 117(3) . . ?
C2 C1 C6 120.1(3) . . ?
C2 C1 N1 119.1(3) . . ?
C6 C1 N1 120.7(3) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 Br1 120.1(3) . . ?
C2 C3 Br1 119.0(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 Br1A 101.9(4) . . ?
C3 C4 Br1A 137.1(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 N2 122.0(3) . . ?
C1 C6 N2 118.5(3) . . ?
O1 C7 N1 122.1(3) . . ?
O1 C7 C8 121.8(3) . . ?
N1 C7 C8 116.1(3) . . ?
C13 C8 C9 119.8(4) . . ?
C13 C8 C7 118.1(3) . . ?
C9 C8 C7 122.1(3) . . ?
C8 C9 C10 120.1(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 119.9(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.4(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 119.6(5) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
O2 C14 N2 128.1(4) . . ?
O2 C14 C15 118.6(3) . . ?
N2 C14 C15 113.2(3) . . ?
F1 C15 F2 107.6(3) . . ?
F1 C15 F3 107.6(3) . . ?
F2 C15 F3 106.2(3) . . ?
F1 C15 C14 111.7(3) . . ?
F2 C15 C14 109.0(3) . . ?
F3 C15 C14 114.4(3) . . ?

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
C7 N1 C1 C2 -60.2(5) . . . . ?
C7 N1 C1 C6 120.0(4) . . . . ?
C6 C1 C2 C3 -2.0(5) . . . . ?
N1 C1 C2 C3 178.2(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C2 C3 Br1 177.4(3) . . . . ?
C2 C3 C4 C5 1.8(6) . . . . ?
Br1 C3 C4 C5 -175.8(3) . . . . ?
C2 C3 C4 Br1A -160.7(6) . . . . ?
C3 C4 C5 C6 -1.2(6) . . . . ?
Br1A C4 C5 C6 166.8(4) . . . . ?
C4 C5 C6 C1 -1.0(5) . . . . ?
C4 C5 C6 N2 178.0(3) . . . . ?
C2 C1 C6 C5 2.6(5) . . . . ?
N1 C1 C6 C5 -177.6(3) . . . . ?
C2 C1 C6 N2 -176.5(3) . . . . ?
N1 C1 C6 N2 3.4(5) . . . . ?
C14 N2 C6 C5 38.4(5) . . . . ?
C14 N2 C6 C1 -142.6(3) . . . . ?
C1 N1 C7 O1 -4.3(5) . . . . ?
C1 N1 C7 C8 177.4(3) . . . . ?
O1 C7 C8 C13 -30.2(5) . . . . ?
N1 C7 C8 C13 148.0(4) . . . . ?
O1 C7 C8 C9 148.1(4) . . . . ?
N1 C7 C8 C9 -33.7(5) . . . . ?
C13 C8 C9 C10 -0.5(6) . . . . ?
C7 C8 C9 C10 -178.7(4) . . . . ?
C8 C9 C10 C11 -0.2(7) . . . . ?
C9 C10 C11 C12 -0.6(7) . . . . ?
C10 C11 C12 C13 2.0(8) . . . . ?
C9 C8 C13 C12 1.9(7) . . . . ?
C7 C8 C13 C12 -179.8(4) . . . . ?
C11 C12 C13 C8 -2.7(8) . . . . ?
C6 N2 C14 O2 -5.4(6) . . . . ?
C6 N2 C14 C15 171.7(3) . . . . ?
O2 C14 C15 F1 -24.3(5) . . . . ?
N2 C14 C15 F1 158.3(3) . . . . ?
O2 C14 C15 F2 94.5(4) . . . . ?
N2 C14 C15 F2 -82.9(4) . . . . ?
O2 C14 C15 F3 -146.8(3) . . . . ?
N2 C14 C15 F3 35.7(4) . . . . ?

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 H1N O1 0.885(19) 1.92(2) 2.761(4) 158(4) 1_655
N2 H2N O1 0.881(19) 1.96(2) 2.830(4) 171(4) 1_655

_refine_diff_density_max         1.815
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.122

####################################################################### 
# 
# 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_DR-43-04
_database_code_depnum_ccdc_archive 'CCDC 1894206'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Dept. of Chemistry, Louisiana State University
United States of America
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2020-03-25 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         'C14 H14 Br F5 N2 O3'
_chemical_formula_sum            'C14 H14 Br F5 N2 O3'
_chemical_formula_weight         433.18

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'
Br Br -0.2901 2.4595 '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                   14.831(9)
_cell_length_b                   13.573(9)
_cell_length_c                   8.294(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.675(18)
_cell_angle_gamma                90
_cell_volume                     1668.8(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    2812
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      26.21
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.532
_shelx_estimated_absorpt_T_min   0.326
_shelx_estimated_absorpt_T_max   0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_T_max  0.823
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15382
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.374
_diffrn_reflns_theta_max         30.627
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5076
_reflns_number_gt                3680
_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 APEX3'
_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    ?
_computing_publication_material  ?
_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)+(0.0506P)²+11.1368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5076
_refine_ls_number_parameters     235
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1744
_refine_ls_wR_factor_gt          0.1621
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.61912(3) 0.56937(4) 0.11256(6) 0.02040(14) Uani 1 1 d . . . . .
F1 F 0.1942(2) 0.9688(2) 0.4993(4) 0.0283(7) Uani 1 1 d . . . . .
F2 F 0.2190(2) 0.8627(2) 0.6924(3) 0.0204(6) Uani 1 1 d . . . . .
F3 F 0.0787(2) 0.8444(4) 0.3518(4) 0.0451(11) Uani 1 1 d . . . . .
F4 F 0.0485(2) 0.8579(4) 0.6010(5) 0.0464(11) Uani 1 1 d . . . . .
F5 F 0.1151(3) 0.7271(3) 0.5154(5) 0.0427(9) Uani 1 1 d . . . . .
O1 O 0.2312(2) 0.4611(3) 0.5346(4) 0.0189(7) Uani 1 1 d . . . . .
O2 O 0.3244(2) 0.4323(3) 0.3248(4) 0.0227(7) Uani 1 1 d . . . . .
O3 O 0.2716(2) 0.8393(3) 0.2867(4) 0.0177(7) Uani 1 1 d . . . . .
N1 N 0.3387(3) 0.5669(3) 0.4916(4) 0.0172(8) Uani 1 1 d D . . . .
H1N H 0.316(4) 0.591(4) 0.574(5) 0.021 Uiso 1 1 d D U . . .
N2 N 0.3369(3) 0.7717(3) 0.5122(4) 0.0153(8) Uani 1 1 d D . . . .
H2N H 0.329(4) 0.764(4) 0.612(3) 0.018 Uiso 1 1 d D U . . .
C1 C 0.4054(3) 0.6214(3) 0.4133(5) 0.0132(8) Uani 1 1 d . . . . .
C2 C 0.4709(3) 0.5740(4) 0.3202(5) 0.0163(8) Uani 1 1 d . . . . .
H2 H 0.4716 0.5043 0.3099 0.020 Uiso 1 1 calc R U . . .
C3 C 0.5341(3) 0.6317(4) 0.2442(5) 0.0158(9) Uani 1 1 d . . . . .
C4 C 0.5367(3) 0.7337(4) 0.2606(5) 0.0165(9) Uani 1 1 d . . . . .
H4 H 0.5817 0.7715 0.2099 0.020 Uiso 1 1 calc R U . . .
C5 C 0.4721(3) 0.7785(4) 0.3526(5) 0.0168(9) Uani 1 1 d . . . . .
H5 H 0.4726 0.8480 0.3655 0.020 Uiso 1 1 calc R U . . .
C6 C 0.4065(3) 0.7228(4) 0.4262(5) 0.0139(8) Uani 1 1 d . . . . .
C7 C 0.2997(3) 0.4799(4) 0.4373(5) 0.0157(9) Uani 1 1 d . . . . .
C8 C 0.1706(3) 0.3765(4) 0.5031(6) 0.0195(9) Uani 1 1 d . . . . .
C9 C 0.1057(4) 0.3860(5) 0.6418(7) 0.0274(12) Uani 1 1 d . . . . .
H9A H 0.1398 0.3839 0.7448 0.041 Uiso 1 1 calc R U . . .
H9B H 0.0624 0.3315 0.6371 0.041 Uiso 1 1 calc R U . . .
H9C H 0.0732 0.4487 0.6325 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1207(4) 0.3922(5) 0.3426(7) 0.0260(11) Uani 1 1 d . . . . .
H10A H 0.0959 0.4591 0.3384 0.039 Uiso 1 1 calc R U . . .
H10B H 0.0714 0.3443 0.3314 0.039 Uiso 1 1 calc R U . . .
H10C H 0.1625 0.3832 0.2544 0.039 Uiso 1 1 calc R U . . .
C11 C 0.2219(4) 0.2808(4) 0.5104(7) 0.0258(11) Uani 1 1 d . . . . .
H11A H 0.2608 0.2761 0.4172 0.039 Uiso 1 1 calc R U . . .
H11B H 0.1792 0.2257 0.5087 0.039 Uiso 1 1 calc R U . . .
H11C H 0.2590 0.2784 0.6100 0.039 Uiso 1 1 calc R U . . .
C12 C 0.2748(3) 0.8256(4) 0.4318(5) 0.0143(8) Uani 1 1 d . . . . .
C13 C 0.2010(3) 0.8716(4) 0.5333(5) 0.0167(9) Uani 1 1 d . . . . .
C14 C 0.1080(4) 0.8249(5) 0.4979(6) 0.0294(12) 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 C3 1.892(5) . ?
F1 C13 1.352(6) . ?
F2 C13 1.344(5) . ?
F3 C14 1.303(7) . ?
F4 C14 1.324(6) . ?
F5 C14 1.338(8) . ?
O1 C7 1.340(5) . ?
O1 C8 1.477(6) . ?
O2 C7 1.201(6) . ?
O3 C12 1.217(5) . ?
N1 C7 1.384(6) . ?
N1 C1 1.409(6) . ?
N2 C12 1.339(6) . ?
N2 C6 1.435(6) . ?
C1 C6 1.380(7) . ?
C1 C2 1.413(6) . ?
C2 C3 1.387(7) . ?
C3 C4 1.391(7) . ?
C4 C5 1.384(6) . ?
C5 C6 1.387(6) . ?
C8 C11 1.505(8) . ?
C8 C10 1.519(7) . ?
C8 C9 1.527(7) . ?
C12 C13 1.534(6) . ?
C13 C14 1.538(7) . ?

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 O1 C8 120.6(4) . . ?
C7 N1 C1 126.2(4) . . ?
C12 N2 C6 120.0(4) . . ?
C6 C1 N1 119.7(4) . . ?
C6 C1 C2 119.3(4) . . ?
N1 C1 C2 121.1(4) . . ?
C3 C2 C1 118.4(5) . . ?
C2 C3 C4 122.3(4) . . ?
C2 C3 Br1 118.7(4) . . ?
C4 C3 Br1 119.0(3) . . ?
C5 C4 C3 118.2(4) . . ?
C4 C5 C6 120.6(5) . . ?
C1 C6 C5 121.1(4) . . ?
C1 C6 N2 119.5(4) . . ?
C5 C6 N2 119.4(4) . . ?
O2 C7 O1 128.2(5) . . ?
O2 C7 N1 125.3(4) . . ?
O1 C7 N1 106.5(4) . . ?
O1 C8 C11 111.1(4) . . ?
O1 C8 C10 109.0(4) . . ?
C11 C8 C10 112.9(4) . . ?
O1 C8 C9 101.3(4) . . ?
C11 C8 C9 111.8(4) . . ?
C10 C8 C9 110.3(4) . . ?
O3 C12 N2 125.6(4) . . ?
O3 C12 C13 118.2(4) . . ?
N2 C12 C13 116.1(4) . . ?
F2 C13 F1 107.7(4) . . ?
F2 C13 C12 112.2(4) . . ?
F1 C13 C12 109.4(4) . . ?
F2 C13 C14 107.6(4) . . ?
F1 C13 C14 107.6(4) . . ?
C12 C13 C14 112.2(4) . . ?
F3 C14 F4 108.7(5) . . ?
F3 C14 F5 109.0(5) . . ?
F4 C14 F5 108.6(5) . . ?
F3 C14 C13 111.5(5) . . ?
F4 C14 C13 110.3(5) . . ?
F5 C14 C13 108.7(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
C7 N1 C1 C6 146.8(5) . . . . ?
C7 N1 C1 C2 -32.6(7) . . . . ?
C6 C1 C2 C3 -0.2(6) . . . . ?
N1 C1 C2 C3 179.2(4) . . . . ?
C1 C2 C3 C4 1.9(7) . . . . ?
C1 C2 C3 Br1 -177.6(3) . . . . ?
C2 C3 C4 C5 -1.8(7) . . . . ?
Br1 C3 C4 C5 177.7(3) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
N1 C1 C6 C5 179.0(4) . . . . ?
C2 C1 C6 C5 -1.6(6) . . . . ?
N1 C1 C6 N2 -3.3(6) . . . . ?
C2 C1 C6 N2 176.1(4) . . . . ?
C4 C5 C6 C1 1.7(7) . . . . ?
C4 C5 C6 N2 -176.0(4) . . . . ?
C12 N2 C6 C1 -109.6(5) . . . . ?
C12 N2 C6 C5 68.1(6) . . . . ?
C8 O1 C7 O2 -4.6(8) . . . . ?
C8 O1 C7 N1 175.6(4) . . . . ?
C1 N1 C7 O2 9.1(8) . . . . ?
C1 N1 C7 O1 -171.1(4) . . . . ?
C7 O1 C8 C11 61.3(6) . . . . ?
C7 O1 C8 C10 -63.7(6) . . . . ?
C7 O1 C8 C9 -179.9(4) . . . . ?
C6 N2 C12 O3 -1.1(7) . . . . ?
C6 N2 C12 C13 177.6(4) . . . . ?
O3 C12 C13 F2 -171.4(4) . . . . ?
N2 C12 C13 F2 9.8(6) . . . . ?
O3 C12 C13 F1 -51.9(6) . . . . ?
N2 C12 C13 F1 129.3(4) . . . . ?
O3 C12 C13 C14 67.4(6) . . . . ?
N2 C12 C13 C14 -111.4(5) . . . . ?
F2 C13 C14 F3 169.6(5) . . . . ?
F1 C13 C14 F3 53.8(6) . . . . ?
C12 C13 C14 F3 -66.6(6) . . . . ?
F2 C13 C14 F4 48.7(6) . . . . ?
F1 C13 C14 F4 -67.1(6) . . . . ?
C12 C13 C14 F4 172.5(5) . . . . ?
F2 C13 C14 F5 -70.3(5) . . . . ?
F1 C13 C14 F5 174.0(4) . . . . ?
C12 C13 C14 F5 53.6(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 H1N O3 0.834(19) 2.13(2) 2.958(5) 174(6) 4_576
N2 H2N F2 0.840(19) 2.23(6) 2.640(5) 110(5) .
N2 H2N O3 0.840(19) 2.21(4) 2.919(5) 142(5) 4_576

_refine_diff_density_max         2.111
_refine_diff_density_min         -1.192
_refine_diff_density_rms         0.156

####################################################################### 
# 
# 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_DL-13-65
_database_code_depnum_ccdc_archive 'CCDC 1953042'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Department of Chemistry  Louisiana State University
United States of America
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_DL-13-65            
;
PROBLEM: Check Calcd Resid. Dens.  0.74A   From Br1             4.22 eA-3
RESPONSE: Residual peaks are near the heaviest atom positions and are reflective of the less than optimal crystal quality. They do not represent missing or misidentified atoms.
;
_vrf_PLAT971_DL-13-65_2          
;
PROBLEM: Check Calcd Resid. Dens.  0.83A   From Br1             4.13 eA-3
RESPONSE: Residual peaks are near the heaviest atom positions and are reflective of the less than optimal crystal quality. They do not represent missing or misidentified atoms.
;
# Added during the CSD deposition process: Wednesday 11 September 2019 07:13 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 Br F3 N2 O2'
_chemical_formula_sum            'C10 H8 Br F3 N2 O2'
_chemical_formula_weight         325.09

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   4.8818(4)
_cell_length_b                   8.8702(11)
_cell_length_c                   13.4150(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.293(6)
_cell_angle_gamma                90
_cell_volume                     580.90(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    2343
_cell_measurement_theta_min      4.17
_cell_measurement_theta_max      28.15
_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.573
_shelx_estimated_absorpt_T_min   0.309
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14035
_diffrn_reflns_av_unetI/netI     0.0854
_diffrn_reflns_av_R_equivalents  0.1107
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         1.518
_diffrn_reflns_theta_max         28.347
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2842
_reflns_number_gt                2571
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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 APEX3'
_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    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1628P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.29(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2842
_refine_ls_number_parameters     171
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2096
_refine_ls_wR_factor_gt          0.2053
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.073
_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
Br1 Br 0.93587(15) 0.51290(15) 0.55033(6) 0.0289(3) Uani 1 1 d . . . . .
F1 F -0.4047(14) 0.3791(10) 0.0713(6) 0.0458(19) Uani 1 1 d . . . . .
F2 F -0.0549(16) 0.4395(13) -0.0156(6) 0.057(2) Uani 1 1 d . . . . .
F3 F -0.2667(19) 0.6039(10) 0.0739(7) 0.049(2) Uani 1 1 d . . . . .
O1 O 0.0544(18) 0.2852(9) 0.1689(8) 0.0374(19) Uani 1 1 d . . . . .
O2 O 0.8686(13) 0.8358(9) 0.2295(6) 0.0254(14) Uani 1 1 d . . . . .
N1 N 0.1186(16) 0.5345(10) 0.2066(6) 0.0249(18) Uani 1 1 d D U . . .
H1N H 0.11(3) 0.627(4) 0.212(10) 0.030 Uiso 1 1 d D U . . .
N2 N 0.4205(15) 0.7910(9) 0.2594(6) 0.0201(14) Uani 1 1 d D U . . .
H2N H 0.288(18) 0.846(13) 0.252(9) 0.024 Uiso 1 1 d D U . . .
C1 C 0.3167(15) 0.5229(15) 0.2844(6) 0.0220(16) Uani 1 1 d . U . . .
C2 C 0.370(2) 0.3887(12) 0.3334(7) 0.0242(19) Uani 1 1 d . U . . .
H2A H 0.2768 0.2993 0.3138 0.029 Uiso 1 1 calc R U . . .
C3 C 0.559(2) 0.3842(13) 0.4112(8) 0.027(2) Uani 1 1 d . U . . .
H3 H 0.5943 0.2922 0.4452 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6964(16) 0.5149(16) 0.4386(6) 0.0238(15) Uani 1 1 d . U . . .
C5 C 0.649(2) 0.6490(12) 0.3893(7) 0.0218(18) Uani 1 1 d . U . . .
H5 H 0.7437 0.7379 0.4089 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4621(18) 0.6532(11) 0.3106(7) 0.0212(18) Uani 1 1 d . U . . .
C7 C 0.0121(19) 0.4158(12) 0.1563(8) 0.0259(19) Uani 1 1 d . U . . .
C8 C -0.182(2) 0.4631(13) 0.0704(8) 0.028(2) Uani 1 1 d . U . . .
C9 C 0.6277(18) 0.8765(11) 0.2245(7) 0.0210(17) Uani 1 1 d . U . . .
C10 C 0.5505(19) 1.0268(17) 0.1820(8) 0.030(2) Uani 1 1 d . U . . .
H10A H 0.6125 1.1068 0.2271 0.044 Uiso 1 1 calc R U . . .
H10B H 0.3510 1.0323 0.1742 0.044 Uiso 1 1 calc R U . . .
H10C H 0.6374 1.0395 0.1168 0.044 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
Br1 C4 1.896(8) . ?
F1 C8 1.319(12) . ?
F2 C8 1.329(13) . ?
F3 C8 1.317(15) . ?
O1 C7 1.188(14) . ?
O2 C9 1.231(11) . ?
N1 C7 1.353(14) . ?
N1 C1 1.423(11) . ?
N1 H1N 0.82(3) . ?
N2 C9 1.350(11) . ?
N2 C6 1.416(13) . ?
N2 H2N 0.82(3) . ?
C1 C2 1.384(16) . ?
C1 C6 1.400(16) . ?
C2 C3 1.390(15) . ?
C2 H2A 0.9500 . ?
C3 C4 1.388(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(16) . ?
C5 C6 1.394(14) . ?
C5 H5 0.9500 . ?
C7 C8 1.546(16) . ?
C9 C10 1.497(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C7 N1 C1 124.6(10) . . ?
C7 N1 H1N 144(10) . . ?
C1 N1 H1N 92(10) . . ?
C9 N2 C6 123.2(8) . . ?
C9 N2 H2N 103(9) . . ?
C6 N2 H2N 133(9) . . ?
C2 C1 C6 119.8(8) . . ?
C2 C1 N1 122.4(11) . . ?
C6 C1 N1 117.8(11) . . ?
C1 C2 C3 120.2(10) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C4 C3 C2 119.6(10) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.9(8) . . ?
C5 C4 Br1 119.2(9) . . ?
C3 C4 Br1 119.8(9) . . ?
C4 C5 C6 119.6(9) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.8(9) . . ?
C5 C6 N2 118.8(9) . . ?
C1 C6 N2 121.3(9) . . ?
O1 C7 N1 128.5(10) . . ?
O1 C7 C8 118.4(10) . . ?
N1 C7 C8 113.1(9) . . ?
F3 C8 F1 106.0(9) . . ?
F3 C8 F2 109.2(10) . . ?
F1 C8 F2 107.9(10) . . ?
F3 C8 C7 115.0(10) . . ?
F1 C8 C7 110.0(9) . . ?
F2 C8 C7 108.6(9) . . ?
O2 C9 N2 122.2(9) . . ?
O2 C9 C10 121.3(9) . . ?
N2 C9 C10 116.4(8) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C7 N1 C1 C2 -16.6(13) . . . . ?
C7 N1 C1 C6 162.8(9) . . . . ?
C6 C1 C2 C3 2.6(14) . . . . ?
N1 C1 C2 C3 -177.9(9) . . . . ?
C1 C2 C3 C4 -0.6(15) . . . . ?
C2 C3 C4 C5 -0.5(15) . . . . ?
C2 C3 C4 Br1 175.7(7) . . . . ?
C3 C4 C5 C6 -0.3(14) . . . . ?
Br1 C4 C5 C6 -176.5(7) . . . . ?
C4 C5 C6 C1 2.2(13) . . . . ?
C4 C5 C6 N2 -178.7(8) . . . . ?
C2 C1 C6 C5 -3.4(14) . . . . ?
N1 C1 C6 C5 177.1(8) . . . . ?
C2 C1 C6 N2 177.5(7) . . . . ?
N1 C1 C6 N2 -2.0(12) . . . . ?
C9 N2 C6 C5 49.6(13) . . . . ?
C9 N2 C6 C1 -131.4(9) . . . . ?
C1 N1 C7 O1 2.5(17) . . . . ?
C1 N1 C7 C8 -175.5(8) . . . . ?
O1 C7 C8 F3 165.8(11) . . . . ?
N1 C7 C8 F3 -15.9(13) . . . . ?
O1 C7 C8 F1 46.3(14) . . . . ?
N1 C7 C8 F1 -135.4(9) . . . . ?
O1 C7 C8 F2 -71.6(13) . . . . ?
N1 C7 C8 F2 106.7(11) . . . . ?
C6 N2 C9 O2 4.5(15) . . . . ?
C6 N2 C9 C10 -173.6(9) . . . . ?

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 H1N O2 0.82(3) 2.21(8) 2.955(12) 150(13) 1_455
N2 H2N O2 0.82(3) 2.07(9) 2.751(10) 141(13) 1_455

_refine_diff_density_max         4.056
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.257

####################################################################### 
# 
# 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_DR-47-25
_database_code_depnum_ccdc_archive 'CCDC 1953043'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Department of Chemistry  Louisiana State University
United States of America
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-03-25 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         'C10 H7 Br F3 N O3'
_chemical_formula_sum            'C10 H7 Br F3 N O3'
_chemical_formula_weight         326.08

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.7597(15)
_cell_length_b                   9.284(2)
_cell_length_c                   15.944(3)
_cell_angle_alpha                88.246(12)
_cell_angle_beta                 81.445(14)
_cell_angle_gamma                88.157(14)
_cell_volume                     1134.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    2155
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      29.31
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.662
_shelx_estimated_absorpt_T_min   0.711
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  0.838
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18073
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.348
_diffrn_reflns_theta_max         33.251
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             11681
_reflns_number_gt                7917
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refined as a 2-component twin by 180 degree rotation about 
reciprocal 0 1 0. Refinement was vs. and hkl5 file prepared by 
TWINABS. The refined BASF parameter was 0.1974(12).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11681
_refine_ls_number_parameters     334
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.90945(4) 0.71827(4) 0.56632(2) 0.01865(9) Uani 1 1 d . . . . .
F1 F 0.7527(3) 0.7711(3) 0.02535(13) 0.0354(6) Uani 1 1 d . . . . .
F2 F 0.5612(3) 0.9220(3) 0.08435(12) 0.0262(5) Uani 1 1 d . . . . .
F3 F 0.8015(3) 0.9965(3) 0.01528(13) 0.0380(6) Uani 1 1 d . . . . .
O1 O 0.7432(3) 0.5199(3) 0.28552(14) 0.0156(5) Uani 1 1 d . . . . .
O2 O 1.0253(3) 0.4846(3) 0.23268(18) 0.0326(7) Uani 1 1 d . . . . .
O3 O 0.9432(3) 0.9547(3) 0.15393(14) 0.0219(6) Uani 1 1 d . . . . .
N1 N 0.7440(4) 0.7873(3) 0.20617(16) 0.0150(6) Uani 1 1 d D . . . .
H1N H 0.674(4) 0.733(4) 0.191(2) 0.018 Uiso 1 1 d D U . . .
C1 C 0.7895(4) 0.6380(4) 0.3287(2) 0.0139(7) Uani 1 1 d . . . . .
C2 C 0.8252(4) 0.6190(4) 0.41125(19) 0.0154(7) Uani 1 1 d . . . . .
H2 H 0.8235 0.5262 0.4381 0.018 Uiso 1 1 calc R U . . .
C3 C 0.8631(4) 0.7395(4) 0.45294(18) 0.0144(7) Uani 1 1 d . . . . .
C4 C 0.8648(4) 0.8753(4) 0.41519(19) 0.0148(7) Uani 1 1 d . . . . .
H4 H 0.8918 0.9565 0.4452 0.018 Uiso 1 1 calc R U . . .
C5 C 0.8265(4) 0.8924(4) 0.33289(19) 0.0158(7) Uani 1 1 d . . . . .
H5 H 0.8267 0.9855 0.3064 0.019 Uiso 1 1 calc R U . . .
C6 C 0.7881(4) 0.7727(4) 0.28972(19) 0.0137(7) Uani 1 1 d . . . . .
C7 C 0.8769(5) 0.4521(4) 0.2342(2) 0.0190(7) Uani 1 1 d . . . . .
C8 C 0.8098(5) 0.3409(4) 0.1835(2) 0.0245(8) Uani 1 1 d . . . . .
H8A H 0.7330 0.3869 0.1465 0.037 Uiso 1 1 calc R U . . .
H8B H 0.7444 0.2706 0.2218 0.037 Uiso 1 1 calc R U . . .
H8C H 0.9079 0.2917 0.1489 0.037 Uiso 1 1 calc R U . . .
C9 C 0.8185(4) 0.8817(4) 0.14826(19) 0.0152(7) Uani 1 1 d . . . . .
C10 C 0.7334(5) 0.8936(4) 0.0664(2) 0.0194(7) Uani 1 1 d . . . . .
Br2 Br 0.41058(4) 0.77992(4) 0.55780(2) 0.01763(9) Uani 1 1 d . . . . .
F4 F 0.1130(3) 0.7076(3) 0.05700(13) 0.0303(6) Uani 1 1 d . . . . .
F5 F 0.3768(3) 0.7017(3) -0.00683(12) 0.0343(6) Uani 1 1 d . . . . .
F6 F 0.2568(3) 0.5057(3) 0.04255(15) 0.0356(6) Uani 1 1 d . . . . .
O4 O 0.2492(3) 1.0087(3) 0.27224(14) 0.0169(5) Uani 1 1 d . . . . .
O5 O 0.5243(3) 1.0848(3) 0.26016(16) 0.0271(6) Uani 1 1 d . . . . .
O6 O 0.4783(3) 0.5968(3) 0.14932(14) 0.0202(5) Uani 1 1 d . . . . .
N2 N 0.2494(4) 0.7469(3) 0.19730(17) 0.0155(6) Uani 1 1 d D . . . .
H2N H 0.174(4) 0.803(4) 0.184(2) 0.019 Uiso 1 1 d D U . . .
C11 C 0.2919(4) 0.8869(4) 0.31859(19) 0.0136(6) Uani 1 1 d . . . . .
C12 C 0.3281(4) 0.8958(4) 0.40127(19) 0.0146(7) Uani 1 1 d . . . . .
H12 H 0.3293 0.9867 0.4269 0.018 Uiso 1 1 calc R U . . .
C13 C 0.3619(4) 0.7706(4) 0.44525(19) 0.0148(7) Uani 1 1 d . . . . .
C14 C 0.3593(4) 0.6362(4) 0.4094(2) 0.0168(7) Uani 1 1 d . . . . .
H14 H 0.3832 0.5509 0.4406 0.020 Uiso 1 1 calc R U . . .
C15 C 0.3213(4) 0.6285(4) 0.3273(2) 0.0162(7) Uani 1 1 d . . . . .
H15 H 0.3174 0.5374 0.3022 0.019 Uiso 1 1 calc R U . . .
C16 C 0.2890(4) 0.7535(4) 0.28201(19) 0.0147(7) Uani 1 1 d . . . . .
C17 C 0.3796(5) 1.1013(4) 0.2422(2) 0.0185(7) Uani 1 1 d . . . . .
C18 C 0.3151(5) 1.2164(5) 0.1868(2) 0.0271(8) Uani 1 1 d . . . . .
H18A H 0.4131 1.2737 0.1599 0.041 Uiso 1 1 calc R U . . .
H18B H 0.2297 1.2789 0.2210 0.041 Uiso 1 1 calc R U . . .
H18C H 0.2598 1.1723 0.1428 0.041 Uiso 1 1 calc R U . . .
C19 C 0.3417(4) 0.6613(4) 0.1408(2) 0.0162(7) Uani 1 1 d . . . . .
C20 C 0.2692(5) 0.6441(4) 0.0577(2) 0.0210(8) 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 C3 1.898(3) . ?
F1 C10 1.322(4) . ?
F2 C10 1.344(4) . ?
F3 C10 1.309(4) . ?
O1 C7 1.371(4) . ?
O1 C1 1.397(4) . ?
O2 C7 1.196(4) . ?
O3 C9 1.215(4) . ?
N1 C9 1.334(4) . ?
N1 C6 1.425(4) . ?
N1 H1N 0.82(2) . ?
C1 C6 1.380(5) . ?
C1 C2 1.390(4) . ?
C2 C3 1.380(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(5) . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(5) . ?
C5 H5 0.9500 . ?
C7 C8 1.483(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.548(4) . ?
Br2 C13 1.893(3) . ?
F4 C20 1.331(4) . ?
F5 C20 1.335(4) . ?
F6 C20 1.324(4) . ?
O4 C17 1.371(4) . ?
O4 C11 1.390(4) . ?
O5 C17 1.203(4) . ?
O6 C19 1.223(4) . ?
N2 C19 1.331(4) . ?
N2 C16 1.432(4) . ?
N2 H2N 0.82(2) . ?
C11 C16 1.387(5) . ?
C11 C12 1.393(4) . ?
C12 C13 1.378(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(5) . ?
C14 C15 1.389(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(5) . ?
C15 H15 0.9500 . ?
C17 C18 1.488(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.530(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
C7 O1 C1 115.7(3) . . ?
C9 N1 C6 123.0(3) . . ?
C9 N1 H1N 117(3) . . ?
C6 N1 H1N 120(3) . . ?
C6 C1 C2 121.6(3) . . ?
C6 C1 O1 118.7(3) . . ?
C2 C1 O1 119.6(3) . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 Br1 119.0(3) . . ?
C4 C3 Br1 119.1(3) . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 N1 119.5(3) . . ?
C5 C6 N1 120.9(3) . . ?
O2 C7 O1 121.7(3) . . ?
O2 C7 C8 127.4(3) . . ?
O1 C7 C8 110.9(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 N1 126.7(3) . . ?
O3 C9 C10 119.2(3) . . ?
N1 C9 C10 114.1(3) . . ?
F3 C10 F1 108.5(3) . . ?
F3 C10 F2 107.8(3) . . ?
F1 C10 F2 106.9(3) . . ?
F3 C10 C9 111.4(3) . . ?
F1 C10 C9 111.0(3) . . ?
F2 C10 C9 111.1(3) . . ?
C17 O4 C11 118.0(3) . . ?
C19 N2 C16 121.0(3) . . ?
C19 N2 H2N 122(3) . . ?
C16 N2 H2N 117(3) . . ?
C16 C11 O4 118.2(3) . . ?
C16 C11 C12 120.1(3) . . ?
O4 C11 C12 121.6(3) . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 121.6(3) . . ?
C12 C13 Br2 119.7(3) . . ?
C14 C13 Br2 118.7(3) . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.3(3) . . ?
C15 C16 N2 120.5(3) . . ?
C11 C16 N2 119.1(3) . . ?
O5 C17 O4 121.7(3) . . ?
O5 C17 C18 127.7(4) . . ?
O4 C17 C18 110.7(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 . . ?
O6 C19 N2 126.1(3) . . ?
O6 C19 C20 117.8(3) . . ?
N2 C19 C20 116.2(3) . . ?
F6 C20 F4 108.2(3) . . ?
F6 C20 F5 107.6(3) . . ?
F4 C20 F5 107.2(3) . . ?
F6 C20 C19 110.0(3) . . ?
F4 C20 C19 113.6(3) . . ?
F5 C20 C19 110.0(3) . . ?

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
C7 O1 C1 C6 88.8(4) . . . . ?
C7 O1 C1 C2 -95.2(4) . . . . ?
C6 C1 C2 C3 -1.3(5) . . . . ?
O1 C1 C2 C3 -177.3(3) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C1 C2 C3 Br1 179.2(2) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
Br1 C3 C4 C5 -178.4(2) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
O1 C1 C6 C5 177.3(3) . . . . ?
C2 C1 C6 N1 -177.5(3) . . . . ?
O1 C1 C6 N1 -1.6(4) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C4 C5 C6 N1 178.4(3) . . . . ?
C9 N1 C6 C1 -144.1(3) . . . . ?
C9 N1 C6 C5 37.0(5) . . . . ?
C1 O1 C7 O2 6.4(5) . . . . ?
C1 O1 C7 C8 -172.9(3) . . . . ?
C6 N1 C9 O3 8.7(6) . . . . ?
C6 N1 C9 C10 -172.1(3) . . . . ?
O3 C9 C10 F3 -6.4(5) . . . . ?
N1 C9 C10 F3 174.3(3) . . . . ?
O3 C9 C10 F1 114.6(4) . . . . ?
N1 C9 C10 F1 -64.7(4) . . . . ?
O3 C9 C10 F2 -126.6(3) . . . . ?
N1 C9 C10 F2 54.1(4) . . . . ?
C17 O4 C11 C16 -110.2(3) . . . . ?
C17 O4 C11 C12 73.1(4) . . . . ?
C16 C11 C12 C13 0.5(5) . . . . ?
O4 C11 C12 C13 177.1(3) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C11 C12 C13 Br2 -179.8(2) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
Br2 C13 C14 C15 179.1(2) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
C14 C15 C16 C11 -0.9(5) . . . . ?
C14 C15 C16 N2 -179.9(3) . . . . ?
O4 C11 C16 C15 -176.5(3) . . . . ?
C12 C11 C16 C15 0.2(5) . . . . ?
O4 C11 C16 N2 2.5(4) . . . . ?
C12 C11 C16 N2 179.2(3) . . . . ?
C19 N2 C16 C15 -45.1(5) . . . . ?
C19 N2 C16 C11 135.8(3) . . . . ?
C11 O4 C17 O5 -5.4(5) . . . . ?
C11 O4 C17 C18 174.0(3) . . . . ?
C16 N2 C19 O6 -10.4(6) . . . . ?
C16 N2 C19 C20 170.1(3) . . . . ?
O6 C19 C20 F6 53.0(4) . . . . ?
N2 C19 C20 F6 -127.5(3) . . . . ?
O6 C19 C20 F4 174.4(3) . . . . ?
N2 C19 C20 F4 -6.1(5) . . . . ?
O6 C19 C20 F5 -65.4(4) . . . . ?
N2 C19 C20 F5 114.1(4) . . . . ?

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 H1N O6 0.82(2) 2.20(2) 3.015(4) 177(4) .
N2 H2N O3 0.82(2) 2.34(2) 3.156(4) 176(4) 1_455

_refine_diff_density_max         1.279
_refine_diff_density_min         -1.029
_refine_diff_density_rms         0.143

####################################################################### 
# 
# 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_DL-13-67B
_database_code_depnum_ccdc_archive 'CCDC 1953046'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Department of Chemistry  Louisiana State University
United States of America
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-03-25 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         'C9 H6 Br2 F3 N O2'
_chemical_formula_sum            'C9 H6 Br2 F3 N O2'
_chemical_formula_weight         376.97

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'
Br Br -0.2901 2.4595 '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                   9.1288(5)
_cell_length_b                   13.8359(7)
_cell_length_c                   9.7608(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.206(2)
_cell_angle_gamma                90
_cell_volume                     1195.14(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    7452
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      33.05
_exptl_crystal_description       'lath fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.095
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    6.810
_shelx_estimated_absorpt_T_min   0.212
_shelx_estimated_absorpt_T_max   0.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.265
_exptl_absorpt_correction_T_max  0.471
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14068
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.301
_diffrn_reflns_theta_max         33.179
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4538
_reflns_number_gt                3699
_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 APEX3'
_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    ?
_computing_publication_material  ?
_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)+(0.0207P)²+1.7755P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4538
_refine_ls_number_parameters     175
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_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
Br2 Br 0.96074(3) 0.55127(2) 0.69013(3) 0.02699(8) Uani 1 1 d . . . . .
F1 F 0.25502(19) 0.09984(11) 0.47614(18) 0.0318(4) Uani 1 1 d . . . . .
F2 F 0.12009(19) 0.18376(12) 0.30679(16) 0.0346(4) Uani 1 1 d . . . . .
F3 F 0.12902(18) 0.22158(13) 0.52151(18) 0.0331(4) Uani 1 1 d . . . . .
O1 O 0.37801(18) 0.27669(11) 0.32587(16) 0.0170(3) Uani 1 1 d . . . . .
N1 N 0.4246(2) 0.27820(14) 0.56580(19) 0.0164(4) Uani 1 1 d . . . . .
H1N H 0.385(3) 0.269(2) 0.632(3) 0.020 Uiso 1 1 d . U . . .
C1 C 0.5530(2) 0.33942(16) 0.5921(2) 0.0150(4) Uani 1 1 d . . . . .
C2 C 0.6879(3) 0.31418(16) 0.5606(2) 0.0166(4) Uani 1 1 d D . . . .
C3 C 0.8117(2) 0.37617(16) 0.5880(2) 0.0181(4) Uani 1 1 d . . . . .
H3 H 0.9030 0.3592 0.5637 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7965(2) 0.46344(16) 0.6519(2) 0.0173(4) Uani 1 1 d . . . . .
C5 C 0.6659(2) 0.49104(15) 0.6892(2) 0.0153(4) Uani 1 1 d . . . . .
H5 H 0.6602 0.5512 0.7346 0.018 Uiso 1 1 calc R U . . .
C6 C 0.5435(2) 0.42849(15) 0.6584(2) 0.0142(4) Uani 1 1 d D . . . .
C7 C 0.3472(2) 0.25415(15) 0.4360(2) 0.0141(4) Uani 1 1 d . . . . .
C8 C 0.2093(3) 0.18920(16) 0.4340(2) 0.0188(4) Uani 1 1 d . . . . .
Br1 Br 0.71295(3) 0.19252(2) 0.47977(3) 0.01967(8) Uani 0.9063(13) 1 d . . P A
1
O2 O 0.4097(2) 0.44503(15) 0.6881(2) 0.0165(3) Uani 0.9063(13) 1 d D . P A 1
C9 C 0.3972(3) 0.5316(2) 0.7662(3) 0.0189(5) Uani 0.9063(13) 1 d D . P A 1
H9A H 0.4747 0.5312 0.8556 0.028 Uiso 0.9063(13) 1 calc R U P A 1
H9B H 0.2968 0.5344 0.7855 0.028 Uiso 0.9063(13) 1 calc R U P A 1
H9C H 0.4114 0.5882 0.7105 0.028 Uiso 0.9063(13) 1 calc R U P A 1
Br1A Br 0.3625(4) 0.4806(2) 0.7124(3) 0.0240(8) Uani 0.0937(13) 1 d . . P A 2
O2A O 0.6550(18) 0.2205(10) 0.5089(16) 0.013(2) Uiso 0.0937(13) 1 d D U P A 2
C9A C 0.792(2) 0.1870(16) 0.476(2) 0.013(2) Uiso 0.0937(13) 1 d D U P A 2
H9A1 H 0.7767 0.1210 0.4386 0.019 Uiso 0.0937(13) 1 calc R U P A 2
H9A2 H 0.8172 0.2295 0.4048 0.019 Uiso 0.0937(13) 1 calc R U P A 2
H9A3 H 0.8744 0.1876 0.5617 0.019 Uiso 0.0937(13) 1 calc R U P A 2


_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
Br2 C4 1.894(2) . ?
F1 C8 1.337(3) . ?
F2 C8 1.309(3) . ?
F3 C8 1.332(3) . ?
O1 C7 1.217(3) . ?
N1 C7 1.333(3) . ?
N1 C1 1.417(3) . ?
N1 H1N 0.82(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.392(3) . ?
C2 O2A 1.396(13) . ?
C2 Br1 1.897(2) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 O2 1.342(3) . ?
C6 Br1A 1.988(4) . ?
C7 C8 1.543(3) . ?
O2 C9 1.439(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O2A C9A 1.441(18) . ?
C9A H9A1 0.9800 . ?
C9A H9A2 0.9800 . ?
C9A H9A3 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
C7 N1 C1 122.95(18) . . ?
C7 N1 H1N 118(2) . . ?
C1 N1 H1N 117(2) . . ?
C2 C1 C6 118.83(19) . . ?
C2 C1 N1 123.3(2) . . ?
C6 C1 N1 117.8(2) . . ?
C1 C2 C3 121.8(2) . . ?
C1 C2 O2A 101.0(7) . . ?
C3 C2 O2A 137.2(7) . . ?
C1 C2 Br1 121.38(16) . . ?
C3 C2 Br1 116.84(17) . . ?
C4 C3 C2 117.3(2) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 123.3(2) . . ?
C3 C4 Br2 119.17(17) . . ?
C5 C4 Br2 117.56(16) . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
O2 C6 C5 125.1(2) . . ?
O2 C6 C1 114.29(19) . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 Br1A 113.21(18) . . ?
C1 C6 Br1A 126.13(18) . . ?
O1 C7 N1 126.3(2) . . ?
O1 C7 C8 120.18(19) . . ?
N1 C7 C8 113.48(18) . . ?
F2 C8 F3 108.4(2) . . ?
F2 C8 F1 108.24(19) . . ?
F3 C8 F1 107.03(19) . . ?
F2 C8 C7 111.18(19) . . ?
F3 C8 C7 111.81(18) . . ?
F1 C8 C7 110.05(19) . . ?
C6 O2 C9 116.79(18) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 O2A C9A 105.0(13) . . ?
O2A C9A H9A1 109.5 . . ?
O2A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
O2A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 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
C7 N1 C1 C2 -66.5(3) . . . . ?
C7 N1 C1 C6 116.0(2) . . . . ?
C6 C1 C2 C3 -2.5(3) . . . . ?
N1 C1 C2 C3 180.0(2) . . . . ?
C6 C1 C2 O2A 175.2(7) . . . . ?
N1 C1 C2 O2A -2.3(7) . . . . ?
C6 C1 C2 Br1 176.83(15) . . . . ?
N1 C1 C2 Br1 -0.7(3) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
O2A C2 C3 C4 -174.9(10) . . . . ?
Br1 C2 C3 C4 -177.57(16) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 Br2 -179.43(16) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
Br2 C4 C5 C6 178.36(16) . . . . ?
C4 C5 C6 O2 179.9(2) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 Br1A -177.94(18) . . . . ?
C2 C1 C6 O2 -178.19(19) . . . . ?
N1 C1 C6 O2 -0.6(3) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
N1 C1 C6 C5 178.99(19) . . . . ?
C2 C1 C6 Br1A 179.49(18) . . . . ?
N1 C1 C6 Br1A -2.9(3) . . . . ?
C1 N1 C7 O1 3.4(4) . . . . ?
C1 N1 C7 C8 -178.3(2) . . . . ?
O1 C7 C8 F2 -14.6(3) . . . . ?
N1 C7 C8 F2 167.0(2) . . . . ?
O1 C7 C8 F3 -135.9(2) . . . . ?
N1 C7 C8 F3 45.7(3) . . . . ?
O1 C7 C8 F1 105.3(2) . . . . ?
N1 C7 C8 F1 -73.1(2) . . . . ?
C5 C6 O2 C9 -4.3(3) . . . . ?
C1 C6 O2 C9 175.20(19) . . . . ?
C1 C2 O2A C9A -178.7(11) . . . . ?
C3 C2 O2A C9A -1.6(18) . . . . ?

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 H1N O1 0.82(3) 2.01(3) 2.781(2) 156(3) 4_566

_refine_diff_density_max         1.026
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_DR-47-30
_database_code_depnum_ccdc_archive 'CCDC 1953044'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Department of Chemistry  Louisiana State University
United States of America
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-03-25 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         'C12 H7 Br F7 N O3'
_chemical_formula_sum            'C12 H7 Br F7 N O3'
_chemical_formula_weight         426.10

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'
Br Br -0.2901 2.4595 '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                   30.172(3)
_cell_length_b                   10.9003(12)
_cell_length_c                   9.0237(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.774(5)
_cell_angle_gamma                90
_cell_volume                     2940.4(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      31.48
_exptl_crystal_description       'needle fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.889
_shelx_estimated_absorpt_T_min   0.610
_shelx_estimated_absorpt_T_max   0.742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_T_max  0.742
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40703
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.362
_diffrn_reflns_theta_max         31.537
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9681
_reflns_number_gt                7940
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0290P)²+2.2479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9681
_refine_ls_number_parameters     441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.30282(2) 0.69052(2) 0.45607(2) 0.02136(5) Uani 1 1 d . . . . .
F1 F 0.45638(4) 0.10851(10) 0.11547(11) 0.0260(2) Uani 1 1 d . . . . .
F2 F 0.49372(3) 0.07425(9) 0.33603(12) 0.0226(2) Uani 1 1 d . . . . .
F3 F 0.43511(4) -0.09340(10) 0.39829(12) 0.0262(2) Uani 1 1 d . . . . .
F4 F 0.38912(3) -0.04574(10) 0.19940(14) 0.0301(3) Uani 1 1 d . . . . .
F5 F 0.43745(4) -0.25756(10) 0.18612(16) 0.0360(3) Uani 1 1 d . . . . .
F6 F 0.49849(4) -0.15364(11) 0.21220(16) 0.0332(3) Uani 1 1 d . . . . .
F7 F 0.44915(5) -0.12339(13) 0.02273(14) 0.0441(3) Uani 1 1 d . . . . .
O1 O 0.28201(4) 0.19213(12) 0.22752(14) 0.0254(3) Uani 1 1 d . . . . .
O2 O 0.33390(4) 0.22092(10) 0.42905(13) 0.0154(2) Uani 1 1 d . . . . .
O3 O 0.42570(4) 0.16718(11) 0.46756(12) 0.0166(2) Uani 1 1 d . . . . .
N1 N 0.40118(4) 0.25204(12) 0.23845(15) 0.0131(2) Uani 1 1 d . . . . .
H1N H 0.4070(7) 0.2603(19) 0.153(2) 0.016 Uiso 1 1 d . U . . .
C1 C 0.34352(5) 0.33705(14) 0.37825(17) 0.0129(3) Uani 1 1 d . . . . .
C2 C 0.32078(5) 0.43623(15) 0.42720(18) 0.0147(3) Uani 1 1 d . . . . .
H2 H 0.2985 0.4246 0.4910 0.018 Uiso 1 1 calc R U . . .
C3 C 0.33108(5) 0.55254(14) 0.38139(18) 0.0147(3) Uani 1 1 d . . . . .
C4 C 0.36292(5) 0.57127(15) 0.28584(19) 0.0168(3) Uani 1 1 d . . . . .
H4 H 0.3688 0.6515 0.2523 0.020 Uiso 1 1 calc R U . . .
C5 C 0.38595(5) 0.47095(15) 0.24020(18) 0.0157(3) Uani 1 1 d . . . . .
H5 H 0.4081 0.4828 0.1760 0.019 Uiso 1 1 calc R U . . .
C6 C 0.37695(5) 0.35292(14) 0.28751(17) 0.0123(3) Uani 1 1 d . . . . .
C7 C 0.30023(5) 0.15691(15) 0.34554(19) 0.0175(3) Uani 1 1 d . . . . .
C8 C 0.29171(7) 0.04123(18) 0.4256(3) 0.0326(4) Uani 1 1 d . . . . .
H8A H 0.2668 -0.0033 0.3684 0.049 Uiso 1 1 calc R U . . .
H8B H 0.2841 0.0611 0.5250 0.049 Uiso 1 1 calc R U . . .
H8C H 0.3186 -0.0101 0.4359 0.049 Uiso 1 1 calc R U . . .
C9 C 0.42439(5) 0.17287(14) 0.33249(17) 0.0125(3) Uani 1 1 d . . . . .
C10 C 0.45239(5) 0.07791(14) 0.25811(17) 0.0133(3) Uani 1 1 d . . . . .
C11 C 0.43260(5) -0.05217(14) 0.25773(18) 0.0149(3) Uani 1 1 d . . . . .
C12 C 0.45505(5) -0.14850(15) 0.1669(2) 0.0196(3) Uani 1 1 d . . . . .
Br2 Br 0.21170(2) 0.65125(2) 0.13583(2) 0.02779(5) Uani 1 1 d . . . . .
F8 F 0.00375(3) 0.05800(9) -0.15948(11) 0.0190(2) Uani 1 1 d . . . . .
F9 F 0.03904(3) 0.10501(9) -0.34806(10) 0.0189(2) Uani 1 1 d . . . . .
F10 F 0.06923(4) -0.09757(10) -0.05033(11) 0.0252(2) Uani 1 1 d . . . . .
F11 F 0.11065(3) -0.03769(10) -0.21683(12) 0.0233(2) Uani 1 1 d . . . . .
F12 F 0.06889(4) -0.25963(10) -0.26645(14) 0.0304(3) Uani 1 1 d . . . . .
F13 F 0.05026(4) -0.12661(11) -0.43889(13) 0.0337(3) Uani 1 1 d . . . . .
F14 F 0.00472(4) -0.17049(11) -0.28403(16) 0.0365(3) Uani 1 1 d . . . . .
O4 O 0.16200(4) 0.19393(11) 0.06377(13) 0.0164(2) Uani 1 1 d . . . . .
O5 O 0.21780(4) 0.17406(13) -0.07738(15) 0.0253(3) Uani 1 1 d . . . . .
O6 O 0.06926(4) 0.16306(10) 0.03264(12) 0.0149(2) Uani 1 1 d . . . . .
N2 N 0.09440(4) 0.24750(12) -0.17385(15) 0.0127(2) Uani 1 1 d . . . . .
H2N H 0.0887(6) 0.2544(19) -0.267(2) 0.015 Uiso 1 1 d . U . . .
C13 C 0.15577(5) 0.31479(14) 0.01501(17) 0.0136(3) Uani 1 1 d . . . . .
C14 C 0.18299(5) 0.40589(15) 0.08475(18) 0.0165(3) Uani 1 1 d . . . . .
H14 H 0.2063 0.3866 0.1631 0.020 Uiso 1 1 calc R U . . .
C15 C 0.17543(5) 0.52564(15) 0.03734(19) 0.0175(3) Uani 1 1 d . . . . .
C16 C 0.14209(5) 0.55574(15) -0.07779(19) 0.0187(3) Uani 1 1 d . . . . .
H16 H 0.1379 0.6384 -0.1099 0.022 Uiso 1 1 calc R U . . .
C17 C 0.11495(5) 0.46329(15) -0.14552(18) 0.0161(3) Uani 1 1 d . . . . .
H17 H 0.0918 0.4829 -0.2240 0.019 Uiso 1 1 calc R U . . .
C18 C 0.12141(5) 0.34205(14) -0.09936(17) 0.0125(3) Uani 1 1 d . . . . .
C19 C 0.19552(5) 0.13031(16) 0.00863(19) 0.0176(3) Uani 1 1 d . . . . .
C20 C 0.19812(6) 0.00252(17) 0.0701(2) 0.0271(4) Uani 1 1 d . . . . .
H20A H 0.1701 -0.0409 0.0361 0.041 Uiso 1 1 calc R U . . .
H20B H 0.2028 0.0058 0.1796 0.041 Uiso 1 1 calc R U . . .
H20C H 0.2231 -0.0409 0.0348 0.041 Uiso 1 1 calc R U . . .
C21 C 0.07096(5) 0.16852(13) -0.10138(17) 0.0116(3) Uani 1 1 d . . . . .
C22 C 0.04451(5) 0.07124(14) -0.20220(17) 0.0123(3) Uani 1 1 d . . . . .
C23 C 0.06817(5) -0.05431(14) -0.18962(17) 0.0139(3) Uani 1 1 d . . . . .
C24 C 0.04736(5) -0.15481(15) -0.2979(2) 0.0185(3) 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 C3 1.8971(15) . ?
F1 C10 1.3507(17) . ?
F2 C10 1.3469(18) . ?
F3 C11 1.3381(19) . ?
F4 C11 1.3478(17) . ?
F5 C12 1.323(2) . ?
F6 C12 1.3204(19) . ?
F7 C12 1.318(2) . ?
O1 C7 1.194(2) . ?
O2 C7 1.3710(19) . ?
O2 C1 1.3902(18) . ?
O3 C9 1.2158(19) . ?
N1 C9 1.340(2) . ?
N1 C6 1.4239(19) . ?
N1 H1N 0.82(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.393(2) . ?
C2 C3 1.382(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(2) . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.493(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.545(2) . ?
C10 C11 1.538(2) . ?
C11 C12 1.544(2) . ?
Br2 C15 1.8971(16) . ?
F8 C22 1.3457(17) . ?
F9 C22 1.3551(17) . ?
F10 C23 1.3387(18) . ?
F11 C23 1.3493(17) . ?
F12 C24 1.3259(19) . ?
F13 C24 1.323(2) . ?
F14 C24 1.3204(19) . ?
O4 C19 1.374(2) . ?
O4 C13 1.3936(19) . ?
O5 C19 1.193(2) . ?
O6 C21 1.2188(19) . ?
N2 C21 1.339(2) . ?
N2 C18 1.4247(19) . ?
N2 H2N 0.84(2) . ?
C13 C14 1.384(2) . ?
C13 C18 1.393(2) . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(2) . ?
C17 H17 0.9500 . ?
C19 C20 1.497(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.547(2) . ?
C22 C23 1.541(2) . ?
C23 C24 1.544(2) . ?

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 O2 C1 117.03(12) . . ?
C9 N1 C6 123.16(13) . . ?
C9 N1 H1N 120.5(15) . . ?
C6 N1 H1N 113.1(15) . . ?
C2 C1 O2 118.11(13) . . ?
C2 C1 C6 121.33(14) . . ?
O2 C1 C6 120.46(13) . . ?
C3 C2 C1 118.67(14) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.50(14) . . ?
C2 C3 Br1 119.41(12) . . ?
C4 C3 Br1 119.05(12) . . ?
C5 C4 C3 118.96(15) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.69(14) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.77(14) . . ?
C1 C6 N1 121.99(14) . . ?
C5 C6 N1 119.22(13) . . ?
O1 C7 O2 122.97(15) . . ?
O1 C7 C8 127.94(16) . . ?
O2 C7 C8 109.10(15) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 N1 127.68(14) . . ?
O3 C9 C10 117.11(13) . . ?
N1 C9 C10 115.21(13) . . ?
F2 C10 F1 108.01(12) . . ?
F2 C10 C11 107.79(12) . . ?
F1 C10 C11 108.07(13) . . ?
F2 C10 C9 108.35(12) . . ?
F1 C10 C9 111.89(12) . . ?
C11 C10 C9 112.55(12) . . ?
F3 C11 F4 108.35(13) . . ?
F3 C11 C10 109.59(13) . . ?
F4 C11 C10 108.06(12) . . ?
F3 C11 C12 107.58(13) . . ?
F4 C11 C12 107.57(13) . . ?
C10 C11 C12 115.48(13) . . ?
F7 C12 F6 108.06(15) . . ?
F7 C12 F5 108.23(15) . . ?
F6 C12 F5 108.70(14) . . ?
F7 C12 C11 111.87(14) . . ?
F6 C12 C11 110.68(14) . . ?
F5 C12 C11 109.22(14) . . ?
C19 O4 C13 115.93(12) . . ?
C21 N2 C18 122.72(13) . . ?
C21 N2 H2N 119.8(14) . . ?
C18 N2 H2N 115.8(14) . . ?
C14 C13 C18 121.35(15) . . ?
C14 C13 O4 119.22(14) . . ?
C18 C13 O4 119.39(13) . . ?
C15 C14 C13 118.26(15) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C16 121.91(15) . . ?
C14 C15 Br2 118.41(12) . . ?
C16 C15 Br2 119.67(13) . . ?
C15 C16 C17 118.96(15) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C18 120.51(15) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 118.98(14) . . ?
C17 C18 N2 119.86(14) . . ?
C13 C18 N2 121.09(14) . . ?
O5 C19 O4 122.76(16) . . ?
O5 C19 C20 127.37(16) . . ?
O4 C19 C20 109.86(14) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 C21 N2 127.72(14) . . ?
O6 C21 C22 117.54(13) . . ?
N2 C21 C22 114.70(13) . . ?
F8 C22 F9 108.14(11) . . ?
F8 C22 C23 108.42(12) . . ?
F9 C22 C23 107.90(12) . . ?
F8 C22 C21 108.90(12) . . ?
F9 C22 C21 111.74(12) . . ?
C23 C22 C21 111.63(12) . . ?
F10 C23 F11 108.39(12) . . ?
F10 C23 C22 109.51(12) . . ?
F11 C23 C22 108.01(12) . . ?
F10 C23 C24 107.48(13) . . ?
F11 C23 C24 107.17(12) . . ?
C22 C23 C24 116.04(13) . . ?
F14 C24 F13 108.24(15) . . ?
F14 C24 F12 108.88(14) . . ?
F13 C24 F12 108.17(14) . . ?
F14 C24 C23 110.49(14) . . ?
F13 C24 C23 111.69(14) . . ?
F12 C24 C23 109.30(13) . . ?

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
C7 O2 C1 C2 89.74(17) . . . . ?
C7 O2 C1 C6 -93.82(17) . . . . ?
O2 C1 C2 C3 177.92(14) . . . . ?
C6 C1 C2 C3 1.5(2) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C1 C2 C3 Br1 -176.44(11) . . . . ?
C2 C3 C4 C5 -2.4(2) . . . . ?
Br1 C3 C4 C5 175.25(12) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C2 C1 C6 C5 -3.0(2) . . . . ?
O2 C1 C6 C5 -179.29(13) . . . . ?
C2 C1 C6 N1 178.86(14) . . . . ?
O2 C1 C6 N1 2.5(2) . . . . ?
C4 C5 C6 C1 1.7(2) . . . . ?
C4 C5 C6 N1 179.95(14) . . . . ?
C9 N1 C6 C1 -57.2(2) . . . . ?
C9 N1 C6 C5 124.59(16) . . . . ?
C1 O2 C7 O1 6.4(2) . . . . ?
C1 O2 C7 C8 -174.14(14) . . . . ?
C6 N1 C9 O3 6.5(3) . . . . ?
C6 N1 C9 C10 -173.86(13) . . . . ?
O3 C9 C10 F2 -47.52(18) . . . . ?
N1 C9 C10 F2 132.80(14) . . . . ?
O3 C9 C10 F1 -166.49(14) . . . . ?
N1 C9 C10 F1 13.83(19) . . . . ?
O3 C9 C10 C11 71.58(18) . . . . ?
N1 C9 C10 C11 -108.10(15) . . . . ?
F2 C10 C11 F3 53.23(15) . . . . ?
F1 C10 C11 F3 169.73(12) . . . . ?
C9 C10 C11 F3 -66.20(16) . . . . ?
F2 C10 C11 F4 171.11(12) . . . . ?
F1 C10 C11 F4 -72.39(15) . . . . ?
C9 C10 C11 F4 51.68(17) . . . . ?
F2 C10 C11 C12 -68.42(17) . . . . ?
F1 C10 C11 C12 48.08(17) . . . . ?
C9 C10 C11 C12 172.15(13) . . . . ?
F3 C11 C12 F7 171.88(14) . . . . ?
F4 C11 C12 F7 55.35(18) . . . . ?
C10 C11 C12 F7 -65.39(19) . . . . ?
F3 C11 C12 F6 -67.55(17) . . . . ?
F4 C11 C12 F6 175.91(14) . . . . ?
C10 C11 C12 F6 55.18(19) . . . . ?
F3 C11 C12 F5 52.09(17) . . . . ?
F4 C11 C12 F5 -64.45(18) . . . . ?
C10 C11 C12 F5 174.82(14) . . . . ?
C19 O4 C13 C14 -82.15(18) . . . . ?
C19 O4 C13 C18 99.95(17) . . . . ?
C18 C13 C14 C15 -0.4(2) . . . . ?
O4 C13 C14 C15 -178.24(14) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C13 C14 C15 Br2 178.49(11) . . . . ?
C14 C15 C16 C17 1.3(3) . . . . ?
Br2 C15 C16 C17 -177.99(12) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C16 C17 C18 C13 -0.5(2) . . . . ?
C16 C17 C18 N2 -177.56(14) . . . . ?
C14 C13 C18 C17 1.0(2) . . . . ?
O4 C13 C18 C17 178.89(13) . . . . ?
C14 C13 C18 N2 178.02(14) . . . . ?
O4 C13 C18 N2 -4.1(2) . . . . ?
C21 N2 C18 C17 -125.70(16) . . . . ?
C21 N2 C18 C13 57.3(2) . . . . ?
C13 O4 C19 O5 -1.0(2) . . . . ?
C13 O4 C19 C20 -179.81(14) . . . . ?
C18 N2 C21 O6 -1.1(2) . . . . ?
C18 N2 C21 C22 -178.88(13) . . . . ?
O6 C21 C22 F8 44.12(18) . . . . ?
N2 C21 C22 F8 -137.82(13) . . . . ?
O6 C21 C22 F9 163.51(13) . . . . ?
N2 C21 C22 F9 -18.43(18) . . . . ?
O6 C21 C22 C23 -75.55(17) . . . . ?
N2 C21 C22 C23 102.51(15) . . . . ?
F8 C22 C23 F10 -55.57(15) . . . . ?
F9 C22 C23 F10 -172.46(12) . . . . ?
C21 C22 C23 F10 64.39(15) . . . . ?
F8 C22 C23 F11 -173.42(11) . . . . ?
F9 C22 C23 F11 69.68(14) . . . . ?
C21 C22 C23 F11 -53.47(16) . . . . ?
F8 C22 C23 C24 66.29(17) . . . . ?
F9 C22 C23 C24 -50.61(17) . . . . ?
C21 C22 C23 C24 -173.76(13) . . . . ?
F10 C23 C24 F14 67.64(17) . . . . ?
F11 C23 C24 F14 -176.03(14) . . . . ?
C22 C23 C24 F14 -55.28(19) . . . . ?
F10 C23 C24 F13 -171.81(13) . . . . ?
F11 C23 C24 F13 -55.48(17) . . . . ?
C22 C23 C24 F13 65.27(18) . . . . ?
F10 C23 C24 F12 -52.15(17) . . . . ?
F11 C23 C24 F12 64.18(17) . . . . ?
C22 C23 C24 F12 -175.07(13) . . . . ?

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 H1N O3 0.82(2) 2.00(2) 2.7904(17) 162(2) 4_565
N2 H2N O6 0.84(2) 2.03(2) 2.8279(17) 158(2) 4_565

_refine_diff_density_max         1.170
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_DR-43-19
_database_code_depnum_ccdc_archive 'CCDC 1894207'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Dept. of Chemistry, Louisiana State University
United States of America
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2020-03-25 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         'C13 H15 Br Cl2 N2 O2'
_chemical_formula_sum            'C13 H15 Br Cl2 N2 O2'
_chemical_formula_weight         382.08

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.492(6)
_cell_length_b                   9.523(8)
_cell_length_c                   9.612(8)
_cell_angle_alpha                78.64(6)
_cell_angle_beta                 78.51(5)
_cell_angle_gamma                79.45(6)
_cell_volume                     738.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    926
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      23.89
_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.147
_shelx_estimated_absorpt_T_min   0.507
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2017
_diffrn_reflns_av_unetI/netI     0.1584
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.193
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measured_fraction_theta_full 0.822
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_Laue_measured_fraction_full 0.822
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_point_group_measured_fraction_full 0.822
_reflns_number_total             2017
_reflns_number_gt                1270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] 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         2017
_refine_ls_number_parameters     182
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.1599
_refine_ls_R_factor_gt           0.1042
_refine_ls_wR_factor_ref         0.3029
_refine_ls_wR_factor_gt          0.2645
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.024
_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
Br1 Br -0.0965(2) 0.5707(3) 0.7730(2) 0.0249(7) Uani 1 1 d . . . . .
Cl1 Cl 0.9770(6) 0.1680(6) 0.5598(6) 0.0272(14) Uani 1 1 d . . . . .
Cl2 Cl 0.8400(6) 0.0189(7) 0.8367(6) 0.0347(16) Uani 1 1 d . . . . .
O1 O 0.4123(14) 0.1321(17) 0.4042(13) 0.018(3) Uani 1 1 d . U . . .
O2 O 0.6622(15) 0.3285(18) 0.6794(14) 0.022(3) Uani 1 1 d . U . . .
N1 N 0.4186(16) 0.3595(18) 0.4321(14) 0.011(3) Uani 1 1 d . U . . .
H1N H 0.4599 0.4401 0.3972 0.013 Uiso 1 1 calc R U . . .
N2 N 0.5231(18) 0.152(2) 0.6589(15) 0.016(4) Uani 1 1 d . U . . .
H2N H 0.5308 0.0627 0.6434 0.019 Uiso 1 1 calc R U . . .
C1 C 0.316(2) 0.349(2) 0.5668(19) 0.013(4) Uani 1 1 d . U . . .
C2 C 0.178(2) 0.449(3) 0.596(2) 0.024(5) Uani 1 1 d . U . . .
H2A H 0.1470 0.5263 0.5236 0.029 Uiso 1 1 calc R U . . .
C3 C 0.086(2) 0.434(3) 0.731(2) 0.017(4) Uani 1 1 d . U . . .
C4 C 0.124(3) 0.320(3) 0.841(2) 0.029(5) Uani 1 1 d . U . . .
H4 H 0.0524 0.3042 0.9301 0.035 Uiso 1 1 calc R U . . .
C5 C 0.279(2) 0.225(2) 0.8118(18) 0.014(4) Uani 1 1 d . U . . .
H5 H 0.3189 0.1545 0.8863 0.017 Uiso 1 1 calc R U . . .
C6 C 0.365(2) 0.241(2) 0.6771(18) 0.015(4) Uani 1 1 d . U . . .
C7 C 0.456(2) 0.251(2) 0.3546(18) 0.015(4) Uani 1 1 d . U . . .
C8 C 0.577(2) 0.276(2) 0.2092(19) 0.018(4) Uani 1 1 d . U . . .
C9 C 0.738(2) 0.182(2) 0.237(2) 0.022(5) Uani 1 1 d . U . . .
H9A H 0.7206 0.0815 0.2727 0.032 Uiso 1 1 calc R U . . .
H9B H 0.8167 0.1867 0.1469 0.032 Uiso 1 1 calc R U . . .
H9C H 0.7804 0.2183 0.3086 0.032 Uiso 1 1 calc R U . . .
C10 C 0.503(2) 0.218(2) 0.0974(18) 0.015(4) Uani 1 1 d . U . . .
H10A H 0.4864 0.1168 0.1338 0.023 Uiso 1 1 calc R U . . .
H10B H 0.3978 0.2771 0.0838 0.023 Uiso 1 1 calc R U . . .
H10C H 0.5771 0.2232 0.0051 0.023 Uiso 1 1 calc R U . . .
C11 C 0.602(3) 0.432(3) 0.153(2) 0.024(5) Uani 1 1 d . U . . .
H11A H 0.4984 0.4913 0.1360 0.036 Uiso 1 1 calc R U . . .
H11B H 0.6441 0.4691 0.2249 0.036 Uiso 1 1 calc R U . . .
H11C H 0.6804 0.4376 0.0632 0.036 Uiso 1 1 calc R U . . .
C12 C 0.655(2) 0.203(3) 0.6652(19) 0.019(5) Uani 1 1 d . U . . .
C13 C 0.805(2) 0.092(2) 0.6586(19) 0.019(5) Uani 1 1 d . U . . .
H13 H 0.7880 0.0123 0.6116 0.022 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
Br1 C3 1.87(2) . ?
Cl1 C13 1.77(2) . ?
Cl2 C13 1.778(19) . ?
O1 C7 1.24(2) . ?
O2 C12 1.25(3) . ?
N1 C7 1.34(3) . ?
N1 C1 1.41(2) . ?
N2 C12 1.32(3) . ?
N2 C6 1.45(2) . ?
C1 C2 1.39(3) . ?
C1 C6 1.39(3) . ?
C2 C3 1.37(3) . ?
C3 C4 1.40(3) . ?
C4 C5 1.46(3) . ?
C5 C6 1.35(2) . ?
C7 C8 1.56(2) . ?
C8 C11 1.52(3) . ?
C8 C9 1.53(2) . ?
C8 C10 1.58(3) . ?
C12 C13 1.50(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
C7 N1 C1 122.5(17) . . ?
C12 N2 C6 120.8(19) . . ?
C2 C1 C6 119.4(18) . . ?
C2 C1 N1 122.4(18) . . ?
C6 C1 N1 117.9(17) . . ?
C3 C2 C1 119(2) . . ?
C2 C3 C4 123(2) . . ?
C2 C3 Br1 119.5(17) . . ?
C4 C3 Br1 118.0(15) . . ?
C3 C4 C5 116.9(19) . . ?
C6 C5 C4 118.4(18) . . ?
C5 C6 C1 122.8(19) . . ?
C5 C6 N2 115.3(17) . . ?
C1 C6 N2 121.4(15) . . ?
O1 C7 N1 121.1(16) . . ?
O1 C7 C8 121.3(18) . . ?
N1 C7 C8 117.1(19) . . ?
C11 C8 C9 110.1(17) . . ?
C11 C8 C7 114.8(17) . . ?
C9 C8 C7 105.8(15) . . ?
C11 C8 C10 109.8(16) . . ?
C9 C8 C10 110.9(17) . . ?
C7 C8 C10 105.4(15) . . ?
O2 C12 N2 126.2(19) . . ?
O2 C12 C13 120.2(19) . . ?
N2 C12 C13 114(2) . . ?
C12 C13 Cl1 111.5(16) . . ?
C12 C13 Cl2 109.1(13) . . ?
Cl1 C13 Cl2 109.0(10) . . ?

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
C7 N1 C1 C2 -125(2) . . . . ?
C7 N1 C1 C6 61(2) . . . . ?
C6 C1 C2 C3 -4(3) . . . . ?
N1 C1 C2 C3 -178.1(18) . . . . ?
C1 C2 C3 C4 -1(3) . . . . ?
C1 C2 C3 Br1 178.2(17) . . . . ?
C2 C3 C4 C5 8(3) . . . . ?
Br1 C3 C4 C5 -171.9(16) . . . . ?
C3 C4 C5 C6 -9(3) . . . . ?
C4 C5 C6 C1 4(3) . . . . ?
C4 C5 C6 N2 175.4(19) . . . . ?
C2 C1 C6 C5 3(3) . . . . ?
N1 C1 C6 C5 177.1(19) . . . . ?
C2 C1 C6 N2 -168(2) . . . . ?
N1 C1 C6 N2 6(3) . . . . ?
C12 N2 C6 C5 -95(2) . . . . ?
C12 N2 C6 C1 77(2) . . . . ?
C1 N1 C7 O1 -6(3) . . . . ?
C1 N1 C7 C8 -177.6(16) . . . . ?
O1 C7 C8 C11 172.7(17) . . . . ?
N1 C7 C8 C11 -16(2) . . . . ?
O1 C7 C8 C9 -66(2) . . . . ?
N1 C7 C8 C9 106(2) . . . . ?
O1 C7 C8 C10 52(2) . . . . ?
N1 C7 C8 C10 -136.7(17) . . . . ?
C6 N2 C12 O2 -4(3) . . . . ?
C6 N2 C12 C13 174.3(14) . . . . ?
O2 C12 C13 Cl1 -38(2) . . . . ?
N2 C12 C13 Cl1 143.3(15) . . . . ?
O2 C12 C13 Cl2 82(2) . . . . ?
N2 C12 C13 Cl2 -96.2(18) . . . . ?

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 H1N O2 0.88 2.30 2.96(2) 131.1 2_666
N2 H2N O1 0.88 1.95 2.82(2) 170.0 2_656

_refine_diff_density_max         2.010
_refine_diff_density_min         -1.205
_refine_diff_density_rms         0.326

####################################################################### 
# 
# 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_DD-13-64
_database_code_depnum_ccdc_archive 'CCDC 1953045'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Department of Chemistry  Louisiana State University
United States of America
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-03-25 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         'C10 H7 Br2 F3 N2 O2'
_chemical_formula_sum            'C10 H7 Br2 F3 N2 O2'
_chemical_formula_weight         404.00

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'
Br Br -0.2901 2.4595 '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                   18.0451(7)
_cell_length_b                   9.1927(3)
_cell_length_c                   7.8491(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.5410(15)
_cell_angle_gamma                90
_cell_volume                     1284.02(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    3506
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      30.98
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.090
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    6.348
_shelx_estimated_absorpt_T_min   0.260
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14117
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.494
_diffrn_reflns_theta_max         33.333
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4955
_reflns_number_gt                3732
_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 APEX3'
_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    ?
_computing_publication_material  ?
_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)+(0.0393P)²+1.2978P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4955
_refine_ls_number_parameters     179
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.68816(2) 0.35974(3) 0.54213(4) 0.01796(7) Uani 1 1 d . . . . .
Br2 Br 0.49259(2) 0.82719(4) 0.34205(4) 0.02344(8) Uani 1 1 d . . . . .
F1 F 0.91404(10) 0.4989(2) 0.9175(2) 0.0277(4) Uani 1 1 d . . . . .
F2 F 0.97656(10) 0.6700(2) 0.8189(2) 0.0252(4) Uani 1 1 d . . . . .
F3 F 0.95871(11) 0.4667(2) 0.6830(2) 0.0316(4) Uani 1 1 d . . . . .
O1 O 0.86165(11) 0.6900(2) 0.5309(2) 0.0167(4) Uani 1 1 d . . . . .
O2 O 0.75841(12) 1.0683(2) 0.5001(2) 0.0175(4) Uani 1 1 d . . . . .
N1 N 0.79120(12) 0.6007(2) 0.7227(3) 0.0114(4) Uani 1 1 d D . . . .
H1N H 0.7887(18) 0.546(3) 0.805(3) 0.014 Uiso 1 1 d D U . . .
N2 N 0.76348(13) 0.8992(2) 0.7126(3) 0.0132(4) Uani 1 1 d D . . . .
H2N H 0.7893(17) 0.871(4) 0.800(3) 0.016 Uiso 1 1 d D U . . .
C1 C 0.72171(14) 0.6549(3) 0.6331(3) 0.0110(4) Uani 1 1 d . . . . .
C2 C 0.70831(14) 0.8051(3) 0.6253(3) 0.0121(4) Uani 1 1 d . . . . .
C3 C 0.63997(14) 0.8587(3) 0.5363(3) 0.0141(4) Uani 1 1 d . . . . .
H3 H 0.6306 0.9603 0.5283 0.017 Uiso 1 1 calc R U . . .
C4 C 0.58658(14) 0.7603(3) 0.4606(3) 0.0158(5) Uani 1 1 d . . . . .
C5 C 0.59793(15) 0.6117(3) 0.4663(3) 0.0162(5) Uani 1 1 d . . . . .
H5 H 0.5600 0.5467 0.4135 0.019 Uiso 1 1 calc R U . . .
C6 C 0.66666(14) 0.5603(3) 0.5517(3) 0.0135(4) Uani 1 1 d . . . . .
C7 C 0.85557(14) 0.6254(3) 0.6632(3) 0.0123(4) Uani 1 1 d . . . . .
C8 C 0.92709(15) 0.5639(3) 0.7738(4) 0.0166(5) Uani 1 1 d . . . . .
C9 C 0.78559(15) 1.0264(3) 0.6462(3) 0.0142(5) Uani 1 1 d . . . . .
C10 C 0.84414(17) 1.1118(3) 0.7624(4) 0.0199(5) Uani 1 1 d . . . . .
H10A H 0.8731 1.1703 0.6923 0.030 Uiso 1 1 calc R U . . .
H10B H 0.8779 1.0448 0.8350 0.030 Uiso 1 1 calc R U . . .
H10C H 0.8197 1.1760 0.8359 0.030 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
Br1 C6 1.888(3) . ?
Br2 C4 1.897(3) . ?
F1 C8 1.331(3) . ?
F2 C8 1.330(3) . ?
F3 C8 1.329(3) . ?
O1 C7 1.217(3) . ?
O2 C9 1.232(3) . ?
N1 C7 1.341(3) . ?
N1 C1 1.422(3) . ?
N1 H1N 0.826(17) . ?
N2 C9 1.367(3) . ?
N2 C2 1.408(3) . ?
N2 H2N 0.805(18) . ?
C1 C6 1.393(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.402(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.539(4) . ?
C9 C10 1.498(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C7 N1 C1 120.8(2) . . ?
C7 N1 H1N 122(2) . . ?
C1 N1 H1N 116(2) . . ?
C9 N2 C2 124.6(2) . . ?
C9 N2 H2N 116(2) . . ?
C2 N2 H2N 119(2) . . ?
C6 C1 C2 119.3(2) . . ?
C6 C1 N1 120.8(2) . . ?
C2 C1 N1 119.9(2) . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 N2 118.7(2) . . ?
C3 C2 N2 121.3(2) . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 123.0(2) . . ?
C5 C4 Br2 116.9(2) . . ?
C3 C4 Br2 120.1(2) . . ?
C4 C5 C6 117.8(2) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C5 C6 C1 121.3(2) . . ?
C5 C6 Br1 119.0(2) . . ?
C1 C6 Br1 119.48(19) . . ?
O1 C7 N1 125.9(2) . . ?
O1 C7 C8 118.4(2) . . ?
N1 C7 C8 115.8(2) . . ?
F3 C8 F2 107.9(2) . . ?
F3 C8 F1 107.7(2) . . ?
F2 C8 F1 108.0(2) . . ?
F3 C8 C7 109.8(2) . . ?
F2 C8 C7 110.1(2) . . ?
F1 C8 C7 113.2(2) . . ?
O2 C9 N2 121.8(2) . . ?
O2 C9 C10 122.3(2) . . ?
N2 C9 C10 115.9(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C7 N1 C1 C6 112.0(3) . . . . ?
C7 N1 C1 C2 -67.6(3) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
N1 C1 C2 C3 179.7(2) . . . . ?
C6 C1 C2 N2 178.1(2) . . . . ?
N1 C1 C2 N2 -2.3(3) . . . . ?
C9 N2 C2 C1 137.0(3) . . . . ?
C9 N2 C2 C3 -45.0(4) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
N2 C2 C3 C4 -176.8(2) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C2 C3 C4 Br2 178.97(18) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
Br2 C4 C5 C6 179.64(18) . . . . ?
C4 C5 C6 C1 1.7(4) . . . . ?
C4 C5 C6 Br1 -173.63(19) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
N1 C1 C6 C5 178.9(2) . . . . ?
C2 C1 C6 Br1 173.73(18) . . . . ?
N1 C1 C6 Br1 -5.9(3) . . . . ?
C1 N1 C7 O1 -1.9(4) . . . . ?
C1 N1 C7 C8 178.7(2) . . . . ?
O1 C7 C8 F3 -61.3(3) . . . . ?
N1 C7 C8 F3 118.1(2) . . . . ?
O1 C7 C8 F2 57.3(3) . . . . ?
N1 C7 C8 F2 -123.3(2) . . . . ?
O1 C7 C8 F1 178.3(2) . . . . ?
N1 C7 C8 F1 -2.3(3) . . . . ?
C2 N2 C9 O2 -0.7(4) . . . . ?
C2 N2 C9 C10 178.8(2) . . . . ?

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 H1N O2 0.826(17) 2.007(19) 2.817(3) 166(3) 4_576
N2 H2N O1 0.805(18) 2.126(18) 2.930(3) 176(3) 4_576

_refine_diff_density_max         1.807
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.147

