# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_import
_database_code_depnum_ccdc_archive 'CCDC 1485121'
_audit_update_record             
;
2016-06-13 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;
_audit_creation_date             2013-06-25T17:12:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        5-bromo-4-fluoro-2-nitrobenzaldehyde
_chemical_formula_moiety         'C7 H3 Br1 F1 N1 O3'
_chemical_formula_sum            'C7 H3 Br F N O3'
_chemical_formula_weight         248.01
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_cell_length_a                   4.9191(2)
_cell_length_b                   6.2146(2)
_cell_length_c                   13.1151(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.211(2)
_cell_angle_gamma                90
_cell_volume                     399.27(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    525
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_measurement_wavelength     0.71073
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    5.135
_exptl_absorpt_correction_T_max  0.3427
_exptl_absorpt_correction_T_min  0.2795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.063
_exptl_crystal_density_method    'not measured'
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5492
_diffrn_reflns_theta_full        27.08
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         3.63
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.9901
_diffrn_measured_fraction_theta_max 0.6144
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.2987E-3
_diffrn_orient_matrix_ub_12      0.104744
_diffrn_orient_matrix_ub_13      0.578922E-1
_diffrn_orient_matrix_ub_21      0.204132
_diffrn_orient_matrix_ub_22      0
_diffrn_orient_matrix_ub_23      0.68065E-2
_diffrn_orient_matrix_ub_31      -0.2561E-3
_diffrn_orient_matrix_ub_32      0.122153
_diffrn_orient_matrix_ub_33      -0.496415E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source                   'Enraf Nonius FR590'
_reflns_number_gt                1587
_reflns_number_total             1734
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         2.042
_refine_diff_density_min         -1.353
_refine_diff_density_rms         0.264
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1734
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0658
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1205P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1575
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_atom_sites_solution_hydrogens   geom
#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1119(12) 0.1307(9) 0.1488(4) 0.0236(12) Uani 1 1 d . . .
C2 C -0.0781(11) 0.2478(12) 0.1990(4) 0.0244(10) Uani 1 1 d . . .
H2 H -0.1392 0.383 0.172 0.029 Uiso 1 1 calc R . .
C3 C -0.1800(11) 0.1708(9) 0.2875(4) 0.0206(11) Uani 1 1 d . . .
C4 C -0.0888(11) -0.0332(9) 0.3234(4) 0.0196(11) Uani 1 1 d . . .
C5 C 0.0987(12) -0.1529(10) 0.2748(5) 0.0238(11) Uani 1 1 d . . .
H5 H 0.159 -0.2895 0.3003 0.029 Uiso 1 1 calc R . .
C6 C 0.1947(12) -0.0670(10) 0.1883(5) 0.0253(12) Uani 1 1 d . . .
C7 C -0.3608(13) 0.3179(11) 0.3411(5) 0.0273(13) Uani 1 1 d . . .
H7 H -0.3922 0.2916 0.4104 0.033 Uiso 1 1 calc R . .
Br1 Br 0.26101(11) 0.24058(16) 0.03341(4) 0.0375(3) Uani 1 1 d . . .
F1 F 0.3812(9) -0.1796(8) 0.1403(3) 0.0417(10) Uani 1 1 d . . .
N1 N -0.1909(10) -0.1296(9) 0.4131(4) 0.0255(10) Uani 1 1 d . . .
O1 O -0.0515(9) -0.2672(10) 0.4608(3) 0.0376(10) Uani 1 1 d . . .
O2 O -0.4182(9) -0.0730(8) 0.4362(4) 0.0387(11) Uani 1 1 d . . .
O3 O -0.4664(11) 0.4695(9) 0.2966(4) 0.0480(15) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.023(3) 0.023(3) 0.025(3) 0.003(2) 0.008(2) -0.005(2)
C2 0.026(2) 0.019(2) 0.028(2) -0.005(3) 0.0009(19) 0.001(3)
C3 0.018(2) 0.018(2) 0.026(3) -0.0016(19) 0.002(2) 0.0053(19)
C4 0.017(3) 0.018(2) 0.023(3) 0.001(2) 0.003(2) -0.001(2)
C5 0.021(3) 0.021(3) 0.029(3) -0.003(2) 0.001(2) 0.007(2)
C6 0.018(3) 0.030(3) 0.029(3) -0.004(2) 0.003(2) 0.008(2)
C7 0.026(3) 0.022(3) 0.034(3) -0.004(2) 0.006(3) 0.004(2)
Br1 0.0381(4) 0.0440(4) 0.0320(4) 0.0083(3) 0.0126(2) -0.0023(3)
F1 0.041(2) 0.043(2) 0.043(2) 0.0002(18) 0.0178(18) 0.0191(18)
N1 0.021(2) 0.026(2) 0.030(2) 0.000(2) 0.0040(18) -0.004(2)
O1 0.039(2) 0.038(2) 0.035(2) 0.019(3) -0.0014(17) 0.001(3)
O2 0.029(2) 0.044(3) 0.045(3) 0.002(2) 0.016(2) 0.004(2)
O3 0.056(4) 0.041(3) 0.048(3) 0.003(2) 0.007(2) 0.035(3)

_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
C1 C2 1.395(8) . ?
C1 C6 1.380(8) . ?
C1 Br1 1.870(6) . ?
C2 H2 0.95 . ?
C2 C3 1.391(8) . ?
C3 C4 1.411(8) . ?
C3 C7 1.495(8) . ?
C4 C5 1.385(8) . ?
C4 N1 1.449(8) . ?
C5 H5 0.95 . ?
C5 C6 1.375(9) . ?
C6 F1 1.354(7) . ?
C7 H7 0.95 . ?
C7 O3 1.201(9) . ?
N1 O1 1.231(7) . ?
N1 O2 1.236(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
C2 C1 Br1 121.3(5) . . ?
C6 C1 C2 118.4(6) . . ?
C6 C1 Br1 120.3(5) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(6) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 117.4(5) . . ?
C2 C3 C7 117.2(6) . . ?
C4 C3 C7 125.3(6) . . ?
C3 C4 N1 121.3(5) . . ?
C5 C4 C3 122.2(5) . . ?
C5 C4 N1 116.5(5) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 C4 117.7(6) . . ?
C6 C5 H5 121.2 . . ?
C5 C6 C1 122.9(5) . . ?
F1 C6 C1 118.4(6) . . ?
F1 C6 C5 118.7(5) . . ?
C3 C7 H7 120 . . ?
O3 C7 C3 120.1(6) . . ?
O3 C7 H7 120 . . ?
O1 N1 C4 118.8(5) . . ?
O1 N1 O2 123.2(5) . . ?
O2 N1 C4 118.0(5) . . ?

_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
####################################################################### 
# 
# 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_import
_database_code_depnum_ccdc_archive 'CCDC 1485122'
_audit_update_record             
;
2016-06-13 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT431_import              
;
PROBLEM: Short Inter HL..A  Contact Br1    ..  O3      ..       2.93 Ang.
RESPONSE: Interaction due to packing 
;
# Added during the CSD deposition process: Monday 13 June 2016 02:58 PM
# end Validation Reply Form

_audit_creation_date             2016-06-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        4-bromo-2-fluoro-5-nitrobenzaldehyde
_chemical_formula_moiety         'C7 H3 Br F N O3'
_chemical_formula_sum            'C7 H3 Br F N O3'
_chemical_formula_weight         248.01
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   10.6934(4)
_cell_length_b                   9.7396(3)
_cell_length_c                   7.4999(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.086(2)
_cell_angle_gamma                90
_cell_volume                     776.71(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    548
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.281
_exptl_absorpt_correction_T_max  0.3874
_exptl_absorpt_correction_T_min  0.3254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.121
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10688
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         2.836
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1765
_reflns_number_total             1777
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1765
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.1979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0787
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(O1A)=Sof(O2A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.21251(2) -0.03655(2) 0.47744(3) 0.02886(12) Uani 1 1 d . . . . .
F1 F 0.02088(13) 0.43334(15) 0.3255(2) 0.0308(3) Uani 1 1 d . . . . .
O1 O 0.5396(6) 0.2381(6) 0.665(3) 0.049(2) Uani 0.73(4) 1 d . . P A 1
O2 O 0.4388(7) 0.0527(10) 0.7118(17) 0.0432(18) Uani 0.73(4) 1 d . . P A 1
O3 O 0.15021(18) 0.67335(18) 0.4133(3) 0.0364(4) Uani 1 1 d . . . . .
N1 N 0.44296(18) 0.1669(2) 0.6527(3) 0.0282(4) Uani 1 1 d . . . . .
C1 C 0.2226(2) 0.4464(3) 0.4850(3) 0.0231(5) Uani 1 1 d . . . . .
C2 C 0.3262(2) 0.3732(2) 0.5647(3) 0.0233(5) Uani 1 1 d . . . . .
H2 H 0.3970 0.4219 0.6197 0.028 Uiso 1 1 calc R . . . .
C3 C 0.3277(2) 0.2317(2) 0.5653(3) 0.0222(4) Uani 1 1 d . . . . .
C4 C 0.2237(2) 0.1564(2) 0.4879(3) 0.0211(4) Uani 1 1 d . . . . .
C5 C 0.1200(2) 0.2278(2) 0.4084(3) 0.0233(5) Uani 1 1 d . . . . .
H5 H 0.0485 0.1794 0.3550 0.028 Uiso 1 1 calc R . . . .
C6 C 0.1216(2) 0.3690(2) 0.4076(3) 0.0219(4) Uani 1 1 d . . . . .
C7 C 0.2283(2) 0.5982(3) 0.4863(3) 0.0296(5) Uani 1 1 d . . . . .
H7 H 0.2999 0.6396 0.5504 0.035 Uiso 1 1 calc R . . . .
O1A O 0.513(3) 0.2354(16) 0.747(5) 0.045(6) Uani 0.27(4) 1 d . . P A 2
O2A O 0.4570(18) 0.0425(14) 0.633(7) 0.049(8) Uani 0.27(4) 1 d . . P A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.03914(18) 0.01405(16) 0.03166(18) 0.00040(8) -0.00430(11) 0.00133(9)
F1 0.0276(7) 0.0231(7) 0.0386(9) 0.0036(6) -0.0107(6) 0.0049(6)
O1 0.0243(18) 0.0382(19) 0.081(7) 0.005(2) -0.010(3) 0.0009(14)
O2 0.043(2) 0.034(2) 0.050(4) 0.014(2) -0.010(2) 0.0088(17)
O3 0.0440(10) 0.0164(8) 0.0467(11) 0.0027(8) -0.0054(8) 0.0023(8)
N1 0.0272(10) 0.0281(11) 0.0278(11) 0.0000(9) -0.0043(8) 0.0061(9)
C1 0.0282(12) 0.0160(11) 0.0243(13) 0.0013(8) -0.0015(9) -0.0004(8)
C2 0.0231(10) 0.0209(11) 0.0247(11) -0.0029(9) -0.0025(9) -0.0018(9)
C3 0.0240(10) 0.0195(11) 0.0224(11) 0.0010(8) -0.0014(8) 0.0029(9)
C4 0.0269(11) 0.0150(11) 0.0209(11) 0.0007(8) 0.0012(8) 0.0012(8)
C5 0.0239(11) 0.0199(11) 0.0250(11) -0.0011(9) -0.0031(9) -0.0013(9)
C6 0.0224(10) 0.0190(10) 0.0231(11) 0.0016(8) -0.0035(8) 0.0036(8)
C7 0.0343(13) 0.0179(12) 0.0351(14) -0.0006(9) -0.0026(10) -0.0040(10)
O1A 0.033(7) 0.035(5) 0.061(13) -0.010(6) -0.020(8) 0.003(4)
O2A 0.038(6) 0.019(4) 0.09(2) -0.007(6) -0.016(8) 0.012(3)

_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 1.885(2) . ?
F1 C6 1.338(2) . ?
O1 N1 1.240(6) . ?
O2 N1 1.200(6) . ?
O3 C7 1.198(3) . ?
N1 C3 1.475(3) . ?
N1 O1A 1.178(11) . ?
N1 O2A 1.232(13) . ?
C1 C2 1.397(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.479(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(3) . ?
C3 C4 1.405(3) . ?
C4 C5 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(3) . ?
C7 H7 0.9500 . ?

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
O1 N1 C3 116.5(3) . . ?
O2 N1 O1 123.6(5) . . ?
O2 N1 C3 119.9(4) . . ?
O1A N1 C3 118.0(7) . . ?
O1A N1 O2A 123.6(13) . . ?
O2A N1 C3 118.2(10) . . ?
C2 C1 C7 118.5(2) . . ?
C6 C1 C2 116.5(2) . . ?
C6 C1 C7 125.0(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 N1 116.0(2) . . ?
C2 C3 C4 120.8(2) . . ?
C4 C3 N1 123.3(2) . . ?
C3 C4 Br1 125.56(17) . . ?
C5 C4 Br1 115.91(17) . . ?
C5 C4 C3 118.5(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
F1 C6 C1 119.3(2) . . ?
F1 C6 C5 117.4(2) . . ?
C5 C6 C1 123.3(2) . . ?
O3 C7 C1 125.5(2) . . ?
O3 C7 H7 117.2 . . ?
C1 C7 H7 117.2 . . ?

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
Br1 C4 C5 C6 -178.89(17) . . . . ?
O1 N1 C3 C2 -22.4(11) . . . . ?
O1 N1 C3 C4 158.3(10) . . . . ?
O2 N1 C3 C2 155.4(9) . . . . ?
O2 N1 C3 C4 -23.9(9) . . . . ?
N1 C3 C4 Br1 -1.1(3) . . . . ?
N1 C3 C4 C5 -179.8(2) . . . . ?
C1 C2 C3 N1 179.6(2) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C1 C6 F1 -178.5(2) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C7 O3 174.9(3) . . . . ?
C2 C3 C4 Br1 179.65(17) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 F1 178.3(2) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C1 C7 O3 -4.2(4) . . . . ?
C7 C1 C2 C3 -178.9(2) . . . . ?
C7 C1 C6 F1 0.7(3) . . . . ?
C7 C1 C6 C5 179.7(2) . . . . ?
O1A N1 C3 C2 16(3) . . . . ?
O1A N1 C3 C4 -163(3) . . . . ?
O2A N1 C3 C2 -169(3) . . . . ?
O2A N1 C3 C4 12(3) . . . . ?

_shelx_res_file                  
;
    import.res created by SHELXL-2014/7

TITL import_a.res in P2(1)/c
REM Old TITL import in P21/a #14
REM SHELXT solution in P2(1)/c
REM R1 0.136, Rweak 0.002, Alpha 0.050, Orientation a'=c, b'=-b, c'=a
REM Formula found by SHELXT: C9 Br F O2
CELL 0.71073 10.6934 9.7396 7.4999 90 96.086 90
ZERR 4 0.0004 0.0003 0.0002 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Br F N O
UNIT 28 12 4 4 4 12

L.S. 10
PLAN  5
TEMP -100
BOND $H
LIST 6
fmap 2
MORE -1
ACTA 52
CONF
OMIT 1 0 0
REM <olex2.extras>
REM <HklSrc "%.\\import.hkl">
REM </olex2.extras>

WGHT    0.048000    0.197900
FVAR       0.65461   0.72562
BR1   3    0.212509   -0.036552    0.477439    11.00000    0.03914    0.01405 =
         0.03166    0.00040   -0.00430    0.00133
F1    4    0.020881    0.433336    0.325510    11.00000    0.02765    0.02312 =
         0.03856    0.00362   -0.01067    0.00492
PART 1
O1    6    0.539650    0.238085    0.665303    21.00000    0.02428    0.03816 =
         0.08092    0.00503   -0.00969    0.00089
O2    6    0.438803    0.052688    0.711813    21.00000    0.04289    0.03386 =
         0.04973    0.01358   -0.00998    0.00879
PART 0
O3    6    0.150210    0.673346    0.413298    11.00000    0.04396    0.01640 =
         0.04668    0.00268   -0.00542    0.00232
N1    5    0.442964    0.166948    0.652696    11.00000    0.02724    0.02811 =
         0.02776    0.00002   -0.00434    0.00606
C1    1    0.222631    0.446449    0.484991    11.00000    0.02820    0.01598 =
         0.02428    0.00129   -0.00150   -0.00045
C2    1    0.326197    0.373186    0.564734    11.00000    0.02309    0.02094 =
         0.02470   -0.00293   -0.00252   -0.00183
AFIX  43
H2    2    0.397014    0.421920    0.619702    11.00000   -1.20000
AFIX   0
C3    1    0.327719    0.231665    0.565278    11.00000    0.02396    0.01947 =
         0.02238    0.00099   -0.00139    0.00295
C4    1    0.223731    0.156436    0.487891    11.00000    0.02693    0.01503 =
         0.02092    0.00072    0.00117    0.00117
C5    1    0.120002    0.227802    0.408417    11.00000    0.02393    0.01994 =
         0.02497   -0.00111   -0.00306   -0.00133
AFIX  43
H5    2    0.048461    0.179442    0.355021    11.00000   -1.20000
AFIX   0
C6    1    0.121597    0.369015    0.407573    11.00000    0.02240    0.01898 =
         0.02309    0.00162   -0.00354    0.00356
C7    1    0.228302    0.598208    0.486280    11.00000    0.03433    0.01786 =
         0.03513   -0.00061   -0.00256   -0.00401
AFIX  43
H7    2    0.299935    0.639601    0.550410    11.00000   -1.20000
AFIX   0
PART 2
O1A   6    0.512513    0.235378    0.747200   -21.00000    0.03256    0.03521 =
         0.06147   -0.00989   -0.02030    0.00280
O2A   6    0.457020    0.042521    0.632539   -21.00000    0.03763    0.01889 =
         0.08634   -0.00655   -0.01551    0.01160
HKLF 4

REM  import_a.res in P2(1)/c
REM R1 =  0.0298 for    1571 Fo > 4sig(Fo)  and  0.0347 for all    1765 data
REM    137 parameters refined using      0 restraints

END

WGHT      0.0480      0.1979

REM Highest difference peak  0.964,  deepest hole -0.716,  1-sigma level  0.103
Q1    1   0.2939 -0.0326  0.4594  11.00000  0.05    0.96
Q2    1   0.1284 -0.0256  0.4970  11.00000  0.05    0.79
Q3    1   0.2736  0.4021  0.5172  11.00000  0.05    0.37
Q4    1   0.3759  0.1996  0.5940  11.00000  0.05    0.35
Q5    1   0.1609  0.4171  0.4886  11.00000  0.05    0.34
;
_shelx_res_checksum              73274
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_N018
_database_code_depnum_ccdc_archive 'CCDC 1485123'
_audit_update_record             
;
2016-06-13 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;

_audit_creation_date             2012-12-13T16:33:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        3-bromo-6-fluoro-2-nitrobenzaldehyde
_chemical_formula_moiety         'C7 H3 Br1 F1 N1 O3'
_chemical_formula_sum            'C7 H3 Br F N O3'
_chemical_formula_weight         248.01
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.7733(2)
_cell_length_b                   14.6188(8)
_cell_length_c                   11.7159(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.404(2)
_cell_angle_gamma                90
_cell_volume                     816.09(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2436
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.495
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    5.024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.4693
_exptl_absorpt_correction_T_max  0.5663

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.195543
_diffrn_orient_matrix_ub_12      -0.66234E-2
_diffrn_orient_matrix_ub_13      0.346023E-1
_diffrn_orient_matrix_ub_21      0.737969E-1
_diffrn_orient_matrix_ub_22      0
_diffrn_orient_matrix_ub_23      -0.781181E-1
_diffrn_orient_matrix_ub_31      0.190232E-1
_diffrn_orient_matrix_ub_32      0.680836E-1
_diffrn_orient_matrix_ub_33      0.33662E-2
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_number            11466
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_full        27.13
_reflns_number_total             1790
_reflns_number_gt                1454
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0318P)²+0.2857P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1790
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.078

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1372(5) 0.66769(17) 0.2263(2) 0.0230(5) Uani 1 1 d . . .
C2 C 1.0262(5) 0.58768(17) 0.1799(2) 0.0243(5) Uani 1 1 d . . .
C3 C 1.1234(6) 0.50396(18) 0.2240(2) 0.0288(6) Uani 1 1 d . . .
H3 H 1.0453 0.4485 0.1943 0.035 Uiso 1 1 calc R . .
C4 C 1.3325(6) 0.50148(19) 0.3106(2) 0.0318(6) Uani 1 1 d . . .
H4 H 1.404 0.4448 0.3393 0.038 Uiso 1 1 calc R . .
C5 C 1.4346(6) 0.58298(18) 0.3542(2) 0.0298(6) Uani 1 1 d . . .
C6 C 1.3408(5) 0.66816(18) 0.3165(2) 0.0255(6) Uani 1 1 d . . .
C7 C 1.4450(6) 0.75292(18) 0.3746(2) 0.0309(6) Uani 1 1 d . . .
H7 H 1.6021 0.748 0.428 0.037 Uiso 1 1 calc R . .
Br1 Br 0.74813(5) 0.589472(18) 0.05883(2) 0.02969(11) Uani 1 1 d . . .
F1 F 1.6386(4) 0.58036(11) 0.43913(14) 0.0420(4) Uani 1 1 d . . .
N1 N 1.0412(5) 0.75567(14) 0.1747(2) 0.0274(5) Uani 1 1 d . . .
O1 O 1.3427(4) 0.82749(13) 0.35831(17) 0.0371(5) Uani 1 1 d . . .
O2 O 1.1886(5) 0.79028(13) 0.10605(18) 0.0404(5) Uani 1 1 d . . .
O3 O 0.8179(4) 0.78577(14) 0.2032(2) 0.0434(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0263(13) 0.0177(13) 0.0253(13) 0.0008(11) 0.0044(11) 0.0011(10)
C2 0.0266(13) 0.0235(13) 0.0223(13) -0.0025(11) -0.0011(10) 0.0015(11)
C3 0.0404(15) 0.0193(14) 0.0264(14) -0.0007(11) -0.0003(12) -0.0044(12)
C4 0.0437(17) 0.0212(14) 0.0298(15) 0.0052(12) -0.0030(13) 0.0018(13)
C5 0.0372(15) 0.0261(15) 0.0252(14) 0.0005(12) -0.0056(12) -0.0005(13)
C6 0.0320(14) 0.0200(14) 0.0245(14) -0.0017(11) 0.0023(12) -0.0032(11)
C7 0.0361(15) 0.0249(16) 0.0313(16) -0.0064(13) -0.0012(12) -0.0035(13)
Br1 0.03067(17) 0.02575(17) 0.03157(17) -0.00208(12) -0.00717(11) -0.00012(12)
F1 0.0544(11) 0.0340(10) 0.0350(10) 0.0029(7) -0.0201(8) -0.0005(8)
N1 0.0296(12) 0.0170(11) 0.0351(13) -0.0035(10) -0.0025(10) -0.0008(10)
O1 0.0432(12) 0.0259(11) 0.0416(12) -0.0082(9) -0.0026(10) 0.0005(9)
O2 0.0527(13) 0.0294(12) 0.0402(12) 0.0109(10) 0.0105(11) -0.0012(10)
O3 0.0305(11) 0.0268(11) 0.0733(16) -0.0004(10) 0.0063(11) 0.0050(9)


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

_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
C1 C2 1.382(4) . ?
C1 C6 1.392(4) . ?
C1 N1 1.482(3) . ?
C2 C3 1.397(4) . ?
C2 Br1 1.884(3) . ?
C3 C4 1.381(4) . ?
C3 H3 0.95 . ?
C4 C5 1.374(4) . ?
C4 H4 0.95 . ?
C5 F1 1.350(3) . ?
C5 C6 1.387(4) . ?
C6 C7 1.486(4) . ?
C7 O1 1.205(3) . ?
C7 H7 0.95 . ?
N1 O2 1.211(3) . ?
N1 O3 1.218(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
C2 C1 C6 122.5(2) . . ?
C2 C1 N1 118.1(2) . . ?
C6 C1 N1 119.4(2) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 Br1 121.40(19) . . ?
C3 C2 Br1 119.62(19) . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
F1 C5 C4 118.3(2) . . ?
F1 C5 C6 117.7(2) . . ?
C4 C5 C6 124.0(3) . . ?
C5 C6 C1 115.8(2) . . ?
C5 C6 C7 120.6(2) . . ?
C1 C6 C7 123.5(2) . . ?
O1 C7 C6 124.1(3) . . ?
O1 C7 H7 118 . . ?
C6 C7 H7 118 . . ?
O2 N1 O3 125.7(2) . . ?
O2 N1 C1 117.1(2) . . ?
O3 N1 C1 117.1(2) . . ?

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 -0.6(4) . . . . ?
N1 C1 C2 C3 177.1(2) . . . . ?
C6 C1 C2 Br1 179.38(19) . . . . ?
N1 C1 C2 Br1 -2.8(3) . . . . ?
C1 C2 C3 C4 -1.7(4) . . . . ?
Br1 C2 C3 C4 178.3(2) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
C3 C4 C5 F1 179.8(2) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
F1 C5 C6 C1 177.9(2) . . . . ?
C4 C5 C6 C1 -2.1(4) . . . . ?
F1 C5 C6 C7 -5.1(4) . . . . ?
C4 C5 C6 C7 174.8(3) . . . . ?
C2 C1 C6 C5 2.5(4) . . . . ?
N1 C1 C6 C5 -175.3(2) . . . . ?
C2 C1 C6 C7 -174.4(2) . . . . ?
N1 C1 C6 C7 7.9(4) . . . . ?
C5 C6 C7 O1 -168.1(3) . . . . ?
C1 C6 C7 O1 8.6(4) . . . . ?
C2 C1 N1 O2 -97.4(3) . . . . ?
C6 C1 N1 O2 80.5(3) . . . . ?
C2 C1 N1 O3 81.0(3) . . . . ?
C6 C1 N1 O3 -101.2(3) . . . . ?

# END of CIF
