# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_d-hnsf-15
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'Br2 C4 O2, C4 H Br2 O2, C6 H6 N3'
_chemical_formula_sum            'C14 H7 Br4 N3 O4'
_chemical_formula_weight         600.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 O1 Cd1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.5626(5)
_cell_length_b                   13.4148(4)
_cell_length_c                   11.3223(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.498(5)
_cell_angle_gamma                90
_cell_volume                     1726.81(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3151
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3790
_cell_measurement_theta_min      2.7620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.0758 before and 0.0334 after
correction. The Ratio of minimum to maximum transmission is 0.33472.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8218
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.495
_diffrn_reflns_theta_min         2.348
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   55.00  101.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.5341    0.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega  -29.00   -3.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.5341   19.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   23.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.5341   19.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   51.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.5341    0.0000   30.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0195510000
_diffrn_orient_matrix_UB_12      0.0273291000
_diffrn_orient_matrix_UB_13      -0.0535762000
_diffrn_orient_matrix_UB_21      -0.0574278000
_diffrn_orient_matrix_UB_22      -0.0196270000
_diffrn_orient_matrix_UB_23      -0.0031105000
_diffrn_orient_matrix_UB_31      -0.0145302000
_diffrn_orient_matrix_UB_32      0.0407510000
_diffrn_orient_matrix_UB_33      0.0344249000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2662
_reflns_number_total             3579
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.749
_refine_diff_density_min         -1.067
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.011
_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)+(0.0300P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0760
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.28354(4) 0.10283(3) 0.60621(4) 0.03307(14) Uani 1 1 d . . . . .
Br2 Br 0.30207(4) -0.14410(3) 0.58359(4) 0.03352(14) Uani 1 1 d . . . . .
Br3 Br -0.01068(5) 0.25715(3) 0.50992(5) 0.04997(18) Uani 1 1 d . . . . .
Br4 Br -0.19987(5) 0.39576(4) 0.62896(5) 0.05393(19) Uani 1 1 d . . . . .
O3 O 0.5177(3) 0.25445(19) 0.6164(3) 0.0396(9) Uani 1 1 d . . . . .
O4 O 0.4386(3) 0.26029(18) 0.4201(3) 0.0323(8) Uani 1 1 d . . . . .
O1 O 0.2628(3) 0.3693(2) 0.4623(3) 0.0423(9) Uani 1 1 d . . . . .
O2 O 0.1328(3) 0.3431(2) 0.2929(3) 0.0450(9) Uani 1 1 d . . . . .
N3 N -0.4422(4) 0.4142(3) 0.3307(3) 0.0332(10) Uani 1 1 d . . . . .
C10 C 0.4168(4) -0.0599(3) 0.5373(3) 0.0178(9) Uani 1 1 d . . . . .
N2 N -0.5026(4) 0.4913(2) 0.3564(3) 0.0344(10) Uani 1 1 d . . . . .
C12 C 0.4068(4) 0.0430(3) 0.5448(3) 0.0176(9) Uani 1 1 d . . . . .
C13 C -0.0062(4) 0.3974(3) 0.5037(3) 0.0243(10) Uani 1 1 d . . . . .
N1 N -0.4451(4) 0.5693(2) 0.3312(3) 0.0309(9) Uani 1 1 d . . . . .
C15 C -0.1676(5) 0.5480(4) 0.2195(4) 0.0473(14) Uani 1 1 d . . . . .
H15 H -0.1060 0.5824 0.1956 0.057 Uiso 1 1 calc R . . . .
C16 C -0.2566(5) 0.6003(3) 0.2542(4) 0.0396(12) Uani 1 1 d . . . . .
H16 H -0.2577 0.6696 0.2544 0.048 Uiso 1 1 calc R . . . .
C17 C 0.4822(4) 0.2163(3) 0.5156(4) 0.0257(10) Uani 1 1 d . . . . .
C18 C -0.2537(5) 0.3877(3) 0.2527(4) 0.0406(13) Uani 1 1 d . . . . .
H18 H -0.2523 0.3184 0.2519 0.049 Uiso 1 1 calc R . . . .
C19 C -0.0844(4) 0.4550(3) 0.5544(3) 0.0228(9) Uani 1 1 d . . . . .
C20 C 0.0778(4) 0.4418(3) 0.4485(3) 0.0226(9) Uani 1 1 d . . . . .
C21 C -0.3446(4) 0.4406(3) 0.2886(3) 0.0283(11) Uani 1 1 d . . . . .
C22 C 0.4915(4) 0.1036(3) 0.5079(3) 0.0195(9) Uani 1 1 d . . . . .
C23 C -0.1666(5) 0.4429(4) 0.2188(4) 0.0483(14) Uani 1 1 d . . . . .
H23 H -0.1042 0.4102 0.1943 0.058 Uiso 1 1 calc R . . . .
C24 C 0.1611(5) 0.3788(3) 0.3923(4) 0.0284(11) Uani 1 1 d . . . . .
C25 C -0.3454(4) 0.5446(3) 0.2893(3) 0.0271(10) Uani 1 1 d . . . . .
H3 H -0.468(5) 0.358(4) 0.343(5) 0.069(19) Uiso 1 1 d . . . . .
H1 H -0.476(5) 0.637(4) 0.349(5) 0.081(18) Uiso 1 1 d . . . . .
H1A H 0.325(6) 0.328(4) 0.439(5) 0.082(19) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.876(4) . ?
Br2 C10 1.887(4) . ?
Br3 C13 1.884(4) . ?
Br4 C19 1.880(4) . ?
O3 C17 1.250(5) . ?
O4 C17 1.254(5) . ?
O1 C24 1.299(6) . ?
O2 C24 1.211(5) . ?
N3 N2 1.311(5) . ?
N3 C21 1.349(6) . ?
C10 C12 1.390(5) . ?
C10 C22 1.389(5) 3_656 ?
N2 N1 1.299(5) . ?
C12 C22 1.393(5) . ?
C13 C19 1.391(5) . ?
C13 C20 1.381(5) . ?
N1 C25 1.364(5) . ?
C15 C16 1.361(7) . ?
C15 C23 1.409(7) . ?
C16 C25 1.385(6) . ?
C17 C22 1.519(5) . ?
C18 C21 1.389(6) . ?
C18 C23 1.360(7) . ?
C19 C20 1.388(5) 3_566 ?
C20 C19 1.388(5) 3_566 ?
C20 C24 1.507(6) . ?
C21 C25 1.396(5) . ?
C22 C10 1.389(5) 3_656 ?

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
N2 N3 C21 112.7(3) . . ?
C12 C10 Br2 120.5(3) . . ?
C22 C10 Br2 118.2(3) 3_656 . ?
C22 C10 C12 121.2(3) 3_656 . ?
N1 N2 N3 105.8(4) . . ?
C10 C12 Br1 121.6(3) . . ?
C10 C12 C22 119.4(3) . . ?
C22 C12 Br1 119.0(3) . . ?
C19 C13 Br3 121.0(3) . . ?
C20 C13 Br3 118.3(3) . . ?
C20 C13 C19 120.8(3) . . ?
N2 N1 C25 112.3(3) . . ?
C16 C15 C23 121.6(5) . . ?
C15 C16 C25 116.4(4) . . ?
O3 C17 O4 127.5(3) . . ?
O3 C17 C22 116.4(4) . . ?
O4 C17 C22 116.1(4) . . ?
C23 C18 C21 116.3(4) . . ?
C13 C19 Br4 121.3(3) . . ?
C20 C19 Br4 118.6(3) 3_566 . ?
C20 C19 C13 120.1(3) 3_566 . ?
C13 C20 C19 119.1(3) . 3_566 ?
C13 C20 C24 120.4(3) . . ?
C19 C20 C24 120.5(4) 3_566 . ?
N3 C21 C18 134.0(4) . . ?
N3 C21 C25 104.7(4) . . ?
C18 C21 C25 121.3(4) . . ?
C10 C22 C12 119.4(3) 3_656 . ?
C10 C22 C17 120.5(3) 3_656 . ?
C12 C22 C17 120.1(3) . . ?
C18 C23 C15 122.4(5) . . ?
O1 C24 C20 112.0(4) . . ?
O2 C24 O1 126.1(4) . . ?
O2 C24 C20 121.9(5) . . ?
N1 C25 C16 133.3(4) . . ?
N1 C25 C21 104.6(4) . . ?
C16 C25 C21 122.1(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1016043'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_w1
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'Br2 C4 O2, C4 H Br2 O2, H2 O, C7 H7 N2'
_chemical_formula_sum            'C15 H10 Br4 N2 O5'
_chemical_formula_weight         617.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.9459(10)
_cell_length_b                   9.0271(9)
_cell_length_c                   12.5435(11)
_cell_angle_alpha                72.408(9)
_cell_angle_beta                 87.358(9)
_cell_angle_gamma                73.572(10)
_cell_volume                     925.31(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2474
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4790
_cell_measurement_theta_min      2.8720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.728
_exptl_absorpt_correction_T_max  0.8611
_exptl_absorpt_correction_T_min  0.6359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.087 before and 0.026 after
correction. The Ratio of minimum to maximum transmission is 0.738474.
The λ/2 correction factor is 0.0015
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6459
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_min         2.376
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                2976
_reflns_number_total             3834
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.851
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.041
_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)+(0.0362P)²+0.4815P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C13(H13), N1(H1), C18(H18), C24(H24), C25(H25), C26(H26)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 -0.37817(6) 0.15624(5) 0.48781(4) 0.03747(15) Uani 1 1 d . . . . .
Br2 Br -0.13817(6) 0.39547(5) 0.42789(5) 0.04273(16) Uani 1 1 d . . . . .
Br3 Br 0.04148(7) 0.81306(7) 0.26896(4) 0.04363(16) Uani 1 1 d . . . . .
Br4 Br 0.13199(7) 1.31558(6) -0.10130(4) 0.04478(16) Uani 1 1 d . . . . .
O2 O 0.2322(4) 0.2565(4) 0.3377(2) 0.0356(8) Uani 1 1 d . . . . .
O1 O 0.2683(4) 0.2412(4) 0.5148(2) 0.0317(8) Uani 1 1 d . . . . .
O4 O 0.0733(4) 1.2021(4) 0.1959(3) 0.0375(8) Uani 1 1 d . . . . .
H4 H 0.1264 1.2264 0.2359 0.056 Uiso 1 1 calc GR . . . .
C4 C 0.0753(5) 1.0526(5) 0.0704(3) 0.0249(10) Uani 1 1 d . . . . .
C5 C -0.0594(5) 0.1669(5) 0.4665(3) 0.0213(9) Uani 1 1 d . . . . .
C6 C 0.0568(5) 1.1327(5) -0.0440(3) 0.0241(9) Uani 1 1 d . . . . .
O3 O 0.3041(4) 1.0562(5) 0.1569(3) 0.0491(10) Uani 1 1 d . . . . .
C8 C 0.2096(5) 0.2088(5) 0.4412(3) 0.0217(9) Uani 1 1 d . . . . .
C9 C -0.1597(5) 0.0677(5) 0.4934(3) 0.0221(9) Uani 1 1 d . . . . .
O5 O 0.6007(5) 0.9019(4) 0.2683(3) 0.0455(9) Uani 1 1 d . . . . .
H5A H 0.5173 0.9700 0.2775 0.068 Uiso 1 1 d G . . . .
H5B H 0.6553 0.8593 0.3293 0.068 Uiso 1 1 d G . . . .
C11 C 0.1008(5) 0.1002(5) 0.4732(3) 0.0197(9) Uani 1 1 d . . . . .
N2 N 0.4796(5) 0.6874(5) 0.2135(4) 0.0428(11) Uani 1 1 d . . . . .
H2 H 0.5282 0.7523 0.2233 0.051 Uiso 1 1 calc R . . . .
C13 C 0.2831(6) 0.5318(6) 0.0523(4) 0.0389(12) Uani 1 1 d . . . . .
H13 H 0.2409 0.4448 0.0679 0.047 Uiso 1 1 calc R . . . .
C14 C 0.0181(5) 0.9200(5) 0.1133(3) 0.0257(10) Uani 1 1 d . . . . .
N1 N 0.3770(5) 0.4878(5) 0.2500(3) 0.0385(10) Uani 1 1 d . . . . .
H1 H 0.3485 0.4038 0.2867 0.046 Uiso 1 1 calc R . . . .
C18 C 0.2785(7) 0.6342(6) -0.0536(4) 0.0430(13) Uani 1 1 d . . . . .
H18 H 0.2311 0.6170 -0.1115 0.052 Uiso 1 1 calc R . . . .
C19 C 0.1639(6) 1.1039(6) 0.1468(4) 0.0305(11) Uani 1 1 d . . . . .
C20 C 0.3537(5) 0.5642(5) 0.1355(4) 0.0311(11) Uani 1 1 d . . . . .
C23 C 0.4195(6) 0.6931(5) 0.1118(4) 0.0313(11) Uani 1 1 d . . . . .
C24 C 0.3432(7) 0.7649(6) -0.0778(4) 0.0439(14) Uani 1 1 d . . . . .
H24 H 0.3370 0.8322 -0.1511 0.053 Uiso 1 1 calc R . . . .
C25 C 0.4154(7) 0.7956(6) 0.0038(4) 0.0430(13) Uani 1 1 d . . . . .
H25 H 0.4595 0.8812 -0.0125 0.052 Uiso 1 1 calc R . . . .
C26 C 0.4499(6) 0.5658(6) 0.2926(4) 0.0418(13) Uani 1 1 d . . . . .
H26 H 0.4768 0.5390 0.3682 0.050 Uiso 1 1 calc R . . . .


_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 C9 1.887(4) . ?
Br2 C5 1.896(4) . ?
Br3 C14 1.890(4) . ?
Br4 C6 1.887(4) . ?
O2 C8 1.264(5) . ?
O1 C8 1.228(5) . ?
O4 C19 1.304(6) . ?
C4 C6 1.391(6) . ?
C4 C14 1.384(6) . ?
C4 C19 1.520(6) . ?
C5 C9 1.401(6) . ?
C5 C11 1.384(6) . ?
C6 C14 1.383(6) 2_575 ?
O3 C19 1.205(6) . ?
C8 C11 1.528(6) . ?
C9 C11 1.392(6) 2_556 ?
C11 C9 1.392(6) 2_556 ?
N2 C23 1.389(6) . ?
N2 C26 1.320(6) . ?
C13 C18 1.365(7) . ?
C13 C20 1.386(7) . ?
C14 C6 1.383(6) 2_575 ?
N1 C20 1.389(6) . ?
N1 C26 1.314(6) . ?
C18 C24 1.404(7) . ?
C20 C23 1.397(6) . ?
C23 C25 1.386(7) . ?
C24 C25 1.369(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C4 C19 120.8(4) . . ?
C14 C4 C6 119.1(4) . . ?
C14 C4 C19 120.1(4) . . ?
C9 C5 Br2 121.1(3) . . ?
C11 C5 Br2 118.0(3) . . ?
C11 C5 C9 120.9(4) . . ?
C4 C6 Br4 118.7(3) . . ?
C14 C6 Br4 121.1(3) 2_575 . ?
C14 C6 C4 120.1(4) 2_575 . ?
O2 C8 C11 115.0(3) . . ?
O1 C8 O2 125.6(4) . . ?
O1 C8 C11 119.5(4) . . ?
C5 C9 Br1 121.5(3) . . ?
C11 C9 Br1 117.7(3) 2_556 . ?
C11 C9 C5 120.9(4) 2_556 . ?
C5 C11 C8 120.7(4) . . ?
C5 C11 C9 118.3(4) . 2_556 ?
C9 C11 C8 121.0(4) 2_556 . ?
C26 N2 C23 108.7(4) . . ?
C18 C13 C20 116.6(5) . . ?
C4 C14 Br3 118.9(3) . . ?
C6 C14 Br3 120.3(3) 2_575 . ?
C6 C14 C4 120.8(4) 2_575 . ?
C26 N1 C20 108.4(4) . . ?
C13 C18 C24 122.0(5) . . ?
O4 C19 C4 113.2(4) . . ?
O3 C19 O4 126.0(4) . . ?
O3 C19 C4 120.8(4) . . ?
C13 C20 N1 131.8(4) . . ?
C13 C20 C23 121.7(4) . . ?
N1 C20 C23 106.5(4) . . ?
N2 C23 C20 105.7(4) . . ?
C25 C23 N2 133.0(5) . . ?
C25 C23 C20 121.2(5) . . ?
C25 C24 C18 121.6(5) . . ?
C24 C25 C23 116.9(5) . . ?
N1 C26 N2 110.7(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1016044'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_d-hnsf-16
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(Br2 C4 O2), 3(H2 O), 2(C9 H8 N O)'
_chemical_formula_sum            'C26 H22 Br4 N2 O9'
_chemical_formula_weight         826.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 O1 Cd1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.2368(6)
_cell_length_b                   11.7277(7)
_cell_length_c                   12.9747(7)
_cell_angle_alpha                72.509(5)
_cell_angle_beta                 86.189(5)
_cell_angle_gamma                73.802(5)
_cell_volume                     1426.42(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3707
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6010
_cell_measurement_theta_min      3.1550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.1079 before and 0.0236 after
correction. The Ratio of minimum to maximum transmission is 0.42976.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.989
_diffrn_reflns_theta_min         2.396
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   77.00   1.0000    4.3500
omega____ theta____ kappa____ phi______ frames
    -       11.5341   57.0000   90.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega  -61.00   36.00   1.0000    4.3500
omega____ theta____ kappa____ phi______ frames
    -       11.5341  -57.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -91.00   15.00   1.0000    4.3500
omega____ theta____ kappa____ phi______ frames
    -      -13.1747  -77.0000 -180.0000 106
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0347639000
_diffrn_orient_matrix_UB_12      0.0394932000
_diffrn_orient_matrix_UB_13      0.0309378000
_diffrn_orient_matrix_UB_21      0.0175810000
_diffrn_orient_matrix_UB_22      0.0510074000
_diffrn_orient_matrix_UB_23      -0.0378471000
_diffrn_orient_matrix_UB_31      -0.0607482000
_diffrn_orient_matrix_UB_32      0.0134665000
_diffrn_orient_matrix_UB_33      -0.0299501000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4535
_reflns_number_total             6630
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6630
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0310P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0812
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29), C31(H31),
 C33(H33), C34(H34), C37(H37), C38(H38), C40(H40)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.60987(4) 0.36249(4) -0.25017(3) 0.04368(11) Uani 1 1 d . . . . .
Br2 Br 0.40149(4) 0.25718(3) -0.35758(3) 0.04501(12) Uani 1 1 d . . . . .
Br3 Br 0.39174(5) 0.07093(4) 0.22137(3) 0.05325(13) Uani 1 1 d . . . . .
Br4 Br 0.19632(4) -0.01849(4) 0.08327(4) 0.05784(13) Uani 1 1 d . . . . .
O8 O 0.1173(3) 0.6701(3) -0.2803(2) 0.0378(6) Uani 1 1 d . . . . .
O5 O 0.1533(3) 0.3733(2) 0.21326(17) 0.0430(6) Uani 1 1 d . . . . .
H5 H 0.2176 0.3625 0.2529 0.065 Uiso 1 1 calc GR . . . .
O6 O -0.0909(3) 0.0737(2) 0.2718(2) 0.0476(7) Uani 1 1 d . . . . .
H6 H -0.1447 0.0507 0.2441 0.071 Uiso 1 1 calc GR . . . .
O9 O 0.3742(3) 0.6877(3) -0.2593(3) 0.0592(8) Uani 1 1 d . . . . .
H9A H 0.3653 0.7271 -0.2128 0.089 Uiso 1 1 d G . . . .
H9B H 0.4567 0.6706 -0.2785 0.089 Uiso 1 1 d G . . . .
N2 N -0.0024(3) 0.3234(3) 0.0838(2) 0.0339(7) Uani 1 1 d . . . . .
O4 O 0.8106(3) 0.5607(2) -0.43638(18) 0.0407(6) Uani 1 1 d . . . . .
C11 C 0.1539(4) 0.3499(3) -0.0600(3) 0.0375(9) Uani 1 1 d . . . . .
O3 O 0.6460(2) 0.6467(2) -0.34024(18) 0.0431(6) Uani 1 1 d . . . . .
C13 C 0.1149(4) 0.3512(3) 0.0455(2) 0.0292(8) Uani 1 1 d . . . . .
C14 C 0.1978(4) 0.3786(3) 0.1122(3) 0.0331(8) Uani 1 1 d . . . . .
C15 C 0.0961(3) -0.0007(3) 0.3904(2) 0.0282(7) Uani 1 1 d . . . . .
C16 C 0.2046(4) -0.2200(3) 0.4625(3) 0.0458(10) Uani 1 1 d . . . . .
H16 H 0.2706 -0.2856 0.5058 0.055 Uiso 1 1 calc R . . . .
O2 O 0.6546(3) 0.1956(2) 0.0956(2) 0.0511(7) Uani 1 1 d . . . . .
C18 C 0.1992(4) -0.0967(3) 0.4553(2) 0.0328(8) Uani 1 1 d . . . . .
O7 O 0.0837(4) 0.4931(3) -0.3678(2) 0.0492(8) Uani 1 1 d . . . . .
C20 C 0.4562(3) 0.3993(3) -0.4382(2) 0.0282(7) Uani 1 1 d . . . . .
C21 C 0.3723(3) -0.0083(3) 0.0362(3) 0.0307(8) Uani 1 1 d . . . . .
C22 C 0.1126(4) -0.2423(3) 0.4056(3) 0.0496(10) Uani 1 1 d . . . . .
H22 H 0.1173 -0.3241 0.4106 0.060 Uiso 1 1 calc R . . . .
C23 C 0.2887(4) -0.0625(4) 0.5096(3) 0.0449(10) Uani 1 1 d . . . . .
H23 H 0.3583 -0.1239 0.5529 0.054 Uiso 1 1 calc R . . . .
C24 C 0.5813(3) 0.0385(3) 0.0577(2) 0.0304(8) Uani 1 1 d . . . . .
C25 C 0.2752(4) 0.3789(4) -0.0988(3) 0.0539(11) Uani 1 1 d . . . . .
H25 H 0.3023 0.3797 -0.1688 0.065 Uiso 1 1 calc R . . . .
C26 C -0.0833(4) 0.2943(3) 0.0261(3) 0.0445(10) Uani 1 1 d . . . . .
H26 H -0.1631 0.2762 0.0556 0.053 Uiso 1 1 calc R . . . .
O1 O 0.7433(3) -0.0008(3) 0.1927(2) 0.0732(10) Uani 1 1 d . . . . .
N1 N 0.0851(3) 0.1194(3) 0.3858(2) 0.0315(7) Uani 1 1 d . . . . .
C29 C 0.0667(5) 0.3187(3) -0.1217(3) 0.0496(11) Uani 1 1 d . . . . .
H29 H 0.0889 0.3173 -0.1920 0.060 Uiso 1 1 calc R . . . .
C30 C 0.0005(4) -0.0246(3) 0.3310(2) 0.0324(8) Uani 1 1 d . . . . .
C31 C 0.1706(4) 0.1490(3) 0.4386(3) 0.0379(9) Uani 1 1 d . . . . .
H31 H 0.1596 0.2318 0.4341 0.046 Uiso 1 1 calc R . . . .
C32 C 0.5896(3) 0.5433(3) -0.4546(2) 0.0294(8) Uani 1 1 d . . . . .
C33 C 0.3142(4) 0.4070(3) 0.0720(3) 0.0454(10) Uani 1 1 d . . . . .
H33 H 0.3684 0.4271 0.1147 0.054 Uiso 1 1 calc R . . . .
C34 C 0.2760(4) 0.0582(4) 0.5001(3) 0.0475(10) Uani 1 1 d . . . . .
H34 H 0.3379 0.0797 0.5350 0.057 Uiso 1 1 calc R . . . .
C35 C 0.6914(4) 0.5876(3) -0.4064(3) 0.0313(8) Uani 1 1 d . . . . .
C36 C 0.5442(3) 0.4429(3) -0.3938(2) 0.0295(8) Uani 1 1 d . . . . .
C37 C 0.3535(4) 0.4061(4) -0.0332(3) 0.0573(11) Uani 1 1 d . . . . .
H37 H 0.4345 0.4245 -0.0589 0.069 Uiso 1 1 calc R . . . .
C38 C -0.0488(5) 0.2911(4) -0.0779(3) 0.0511(11) Uani 1 1 d . . . . .
H38 H -0.1050 0.2699 -0.1182 0.061 Uiso 1 1 calc R . . . .
C39 C 0.4533(4) 0.0302(3) 0.0929(2) 0.0307(8) Uani 1 1 d . . . . .
C40 C 0.0113(4) -0.1468(3) 0.3399(3) 0.0432(9) Uani 1 1 d . . . . .
H40 H -0.0494 -0.1661 0.3019 0.052 Uiso 1 1 calc R . . . .
C41 C 0.6685(4) 0.0826(4) 0.1204(3) 0.0435(10) Uani 1 1 d . . . . .
H8A H 0.114(4) 0.619(3) -0.302(3) 0.038(12) Uiso 1 1 d . . . . .
H2 H -0.034(4) 0.325(3) 0.149(3) 0.057(12) Uiso 1 1 d . . . . .
H8B H 0.191(5) 0.679(4) -0.287(3) 0.057(15) Uiso 1 1 d . . . . .
H1 H 0.025(4) 0.181(3) 0.349(3) 0.049(12) Uiso 1 1 d . . . . .
H7A H 0.017(4) 0.513(4) -0.382(3) 0.039(14) Uiso 1 1 d . . . . .
H7B H 0.124(5) 0.475(4) -0.423(4) 0.075(16) Uiso 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 C36 1.889(3) . ?
Br2 C20 1.892(3) . ?
Br3 C39 1.890(3) . ?
Br4 C21 1.887(3) . ?
O5 C14 1.349(4) . ?
O6 C30 1.325(4) . ?
N2 C13 1.355(4) . ?
N2 C26 1.325(4) . ?
O4 C35 1.239(4) . ?
C11 C13 1.403(4) . ?
C11 C25 1.401(5) . ?
C11 C29 1.422(5) . ?
O3 C35 1.249(4) . ?
C13 C14 1.410(4) . ?
C14 C33 1.354(5) . ?
C15 C18 1.406(4) . ?
C15 N1 1.365(4) . ?
C15 C30 1.419(4) . ?
C16 C18 1.406(4) . ?
C16 C22 1.358(5) . ?
O2 C41 1.235(4) . ?
C18 C23 1.399(5) . ?
C20 C32 1.398(4) 2_664 ?
C20 C36 1.381(4) . ?
C21 C24 1.388(4) 2_655 ?
C21 C39 1.387(4) . ?
C22 C40 1.397(5) . ?
C23 C34 1.354(5) . ?
C24 C21 1.388(4) 2_655 ?
C24 C39 1.379(5) . ?
C24 C41 1.527(4) . ?
C25 C37 1.366(5) . ?
C26 C38 1.382(5) . ?
O1 C41 1.245(4) . ?
N1 C31 1.321(4) . ?
C29 C38 1.356(6) . ?
C30 C40 1.376(4) . ?
C31 C34 1.377(5) . ?
C32 C20 1.398(4) 2_664 ?
C32 C35 1.526(4) . ?
C32 C36 1.388(4) . ?
C33 C37 1.399(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
C26 N2 C13 123.0(3) . . ?
C13 C11 C29 117.5(4) . . ?
C25 C11 C13 118.8(3) . . ?
C25 C11 C29 123.7(3) . . ?
N2 C13 C11 119.3(3) . . ?
N2 C13 C14 120.0(3) . . ?
C11 C13 C14 120.7(3) . . ?
O5 C14 C13 115.9(3) . . ?
O5 C14 C33 125.1(3) . . ?
C33 C14 C13 119.0(3) . . ?
C18 C15 C30 122.1(3) . . ?
N1 C15 C18 119.3(3) . . ?
N1 C15 C30 118.6(3) . . ?
C22 C16 C18 119.4(3) . . ?
C16 C18 C15 118.2(3) . . ?
C23 C18 C15 117.3(3) . . ?
C23 C18 C16 124.5(3) . . ?
C32 C20 Br2 118.8(2) 2_664 . ?
C36 C20 Br2 120.8(2) . . ?
C36 C20 C32 120.4(3) . 2_664 ?
C24 C21 Br4 118.5(2) 2_655 . ?
C39 C21 Br4 121.1(3) . . ?
C39 C21 C24 120.4(3) . 2_655 ?
C16 C22 C40 122.4(3) . . ?
C34 C23 C18 121.2(3) . . ?
C21 C24 C41 121.0(3) 2_655 . ?
C39 C24 C21 118.8(3) . 2_655 ?
C39 C24 C41 120.2(3) . . ?
C37 C25 C11 119.6(4) . . ?
N2 C26 C38 119.8(4) . . ?
C31 N1 C15 122.1(3) . . ?
C38 C29 C11 120.0(3) . . ?
O6 C30 C15 116.5(3) . . ?
O6 C30 C40 126.2(3) . . ?
C40 C30 C15 117.3(3) . . ?
N1 C31 C34 120.6(3) . . ?
C20 C32 C35 120.7(3) 2_664 . ?
C36 C32 C20 118.8(3) . 2_664 ?
C36 C32 C35 120.5(3) . . ?
C14 C33 C37 120.6(3) . . ?
C23 C34 C31 119.5(3) . . ?
O4 C35 O3 126.6(3) . . ?
O4 C35 C32 116.8(3) . . ?
O3 C35 C32 116.5(3) . . ?
C20 C36 Br1 120.3(2) . . ?
C20 C36 C32 120.8(3) . . ?
C32 C36 Br1 118.8(2) . . ?
C25 C37 C33 121.2(4) . . ?
C29 C38 C26 120.4(3) . . ?
C21 C39 Br3 120.8(3) . . ?
C24 C39 Br3 118.3(2) . . ?
C24 C39 C21 120.8(3) . . ?
C30 C40 C22 120.6(3) . . ?
O2 C41 C24 116.9(3) . . ?
O2 C41 O1 127.8(3) . . ?
O1 C41 C24 115.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1016045'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_w1
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H7 N3 O2, 0.5(C8 H2 Br4 O4)'
_chemical_formula_sum            'C16 H8 Br2 N3 O4'
_chemical_formula_weight         466.05
_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 0.0030 0.0020 '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 -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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                   17.4367(5)
_cell_length_b                   11.5949(2)
_cell_length_c                   18.1466(11)
_cell_angle_alpha                90
_cell_angle_beta                 121.166(3)
_cell_angle_gamma                90
_cell_volume                     3139.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9393
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5000
_cell_measurement_theta_min      2.8380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.193
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.1079 before and 0.0236 after
correction. The Ratio of minimum to maximum transmission is 0.42976.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.058 before and 0.039 after
correction. The Ratio of minimum to maximum transmission is 0.2798.
The λ/2 correction factor is 0.0015
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32815
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.192
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                4898
_reflns_number_total             6842
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6842
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.020
_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)+(0.0348P)²+6.0422P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.1032
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2.a Riding coordinates:
 O1(H1A), O4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C15(H15), C30(H30), C32(H32), C34(H34), C41(H41), C51(H51), C1(H1),
 C24(H24), C33(H33), C38(H38), C40(H40), C46(H46), C50(H50)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O5 O -0.4963(3) -0.0085(4) -0.3216(3) 0.0831(13) Uani 1 1 d . . . . .
O6 O -0.3953(4) -0.0543(6) -0.1933(4) 0.128(2) Uani 1 1 d . . . . .
N2 N -0.4197(4) -0.0292(4) -0.2676(4) 0.0739(14) Uani 1 1 d . . . . .
N5 N -0.1028(2) -0.0351(3) -0.2035(2) 0.0496(9) Uani 1 1 d . . . . .
N6 N -0.1663(2) 0.0416(3) -0.3653(2) 0.0396(8) Uani 1 1 d . . . . .
C9 C -0.1290(5) -0.1149(4) -0.0968(3) 0.0715(17) Uani 1 1 d . . . . .
H9 H -0.1048 -0.1487 -0.0427 0.086 Uiso 1 1 calc R . . . .
C12 C -0.2252(3) 0.0228(3) -0.3401(2) 0.0337(8) Uani 1 1 d . . . . .
C15 C -0.3464(3) 0.0858(4) -0.4791(3) 0.0549(12) Uani 1 1 d . . . . .
H15 H -0.4066 0.1031 -0.5167 0.066 Uiso 1 1 calc R . . . .
C19 C -0.2550(3) -0.0483(3) -0.2284(3) 0.0459(11) Uani 1 1 d . . . . .
C22 C -0.3177(3) 0.0454(3) -0.3957(3) 0.0414(10) Uani 1 1 d . . . . .
C27 C -0.1927(3) -0.0213(3) -0.2541(3) 0.0381(9) Uani 1 1 d . . . . .
C30 C -0.0734(4) -0.0795(4) -0.1268(3) 0.0659(15) Uani 1 1 d . . . . .
H30 H -0.0119 -0.0880 -0.0903 0.079 Uiso 1 1 calc R . . . .
C32 C -0.3774(3) 0.0256(4) -0.3671(3) 0.0508(11) Uani 1 1 d . . . . .
H32 H -0.4378 0.0436 -0.4029 0.061 Uiso 1 1 calc R . . . .
C34 C -0.2869(4) 0.0992(4) -0.5043(3) 0.0610(13) Uani 1 1 d . . . . .
H34 H -0.3054 0.1221 -0.5602 0.073 Uiso 1 1 calc R . . . .
C35 C -0.3491(3) -0.0185(4) -0.2894(3) 0.0490(12) Uani 1 1 d . . . . .
C41 C -0.1973(3) 0.0781(4) -0.4453(3) 0.0526(11) Uani 1 1 d . . . . .
H41 H -0.1563 0.0903 -0.4626 0.063 Uiso 1 1 calc R . . . .
C51 C -0.2185(5) -0.0991(4) -0.1476(4) 0.0657(15) Uani 1 1 d . . . . .
H51 H -0.2562 -0.1224 -0.1282 0.079 Uiso 1 1 calc R . . . .
O7 O 0.1314(3) -0.3267(4) -0.4203(2) 0.0910(13) Uani 1 1 d . . . . .
O8 O 0.0350(2) -0.2218(4) -0.4149(2) 0.0767(11) Uani 1 1 d . . . . .
N1 N 0.1111(2) -0.2593(3) -0.3831(2) 0.0462(9) Uani 1 1 d . . . . .
N3 N 0.4222(2) -0.1874(3) -0.1440(2) 0.0450(8) Uani 1 1 d . . . . .
N4 N 0.3578(2) -0.1161(3) -0.0444(2) 0.0373(7) Uani 1 1 d . . . . .
C1 C 0.3260(3) -0.0783(4) 0.0032(3) 0.0454(10) Uani 1 1 d . . . . .
H1 H 0.3666 -0.0542 0.0590 0.054 Uiso 1 1 calc R . . . .
C13 C 0.2728(3) -0.2243(3) -0.2653(2) 0.0332(8) Uani 1 1 d . . . . .
C14 C 0.1783(3) -0.2218(3) -0.2954(2) 0.0357(9) Uani 1 1 d . . . . .
C17 C 0.2982(2) -0.1506(3) -0.1260(2) 0.0320(8) Uani 1 1 d . . . . .
C21 C 0.2055(3) -0.1484(3) -0.1596(2) 0.0343(8) Uani 1 1 d . . . . .
C24 C 0.1463(3) -0.1859(3) -0.2461(3) 0.0396(9) Uani 1 1 d . . . . .
H24 H 0.0848 -0.1855 -0.2686 0.047 Uiso 1 1 calc R . . . .
C26 C 0.3322(2) -0.1888(3) -0.1803(2) 0.0335(8) Uani 1 1 d . . . . .
C33 C 0.1740(3) -0.1088(4) -0.1069(3) 0.0450(10) Uani 1 1 d . . . . .
H33 H 0.1129 -0.1074 -0.1270 0.054 Uiso 1 1 calc R . . . .
C38 C 0.3112(3) -0.2564(4) -0.3145(3) 0.0447(10) Uani 1 1 d . . . . .
H38 H 0.2749 -0.2812 -0.3711 0.054 Uiso 1 1 calc R . . . .
C40 C 0.4543(3) -0.2173(4) -0.1929(3) 0.0525(11) Uani 1 1 d . . . . .
H40 H 0.5161 -0.2160 -0.1687 0.063 Uiso 1 1 calc R . . . .
C46 C 0.4016(3) -0.2507(4) -0.2782(3) 0.0501(11) Uani 1 1 d . . . . .
H46 H 0.4277 -0.2690 -0.3102 0.060 Uiso 1 1 calc R . . . .
C50 C 0.2347(3) -0.0726(4) -0.0257(3) 0.0488(11) Uani 1 1 d . . . . .
H50 H 0.2156 -0.0443 0.0101 0.059 Uiso 1 1 calc R . . . .
Br1 Br -0.35504(3) -0.41468(4) -0.21479(3) 0.05583(14) Uani 1 1 d . . . . .
Br2 Br -0.13173(3) -0.43950(4) -0.09839(3) 0.05833(15) Uani 1 1 d . . . . .
Br3 Br -0.10956(3) -0.27093(5) -0.37750(3) 0.06210(15) Uani 1 1 d . . . . .
Br4 Br -0.32985(3) -0.23810(4) -0.49146(3) 0.06048(15) Uani 1 1 d . . . . .
O1 O -0.01327(18) -0.4669(2) -0.2174(2) 0.0505(8) Uani 1 1 d . . . . .
H1A H 0.0412 -0.4665 -0.1963 0.061 Uiso 1 1 d R . . . .
O2 O 0.0107(2) -0.2985(3) -0.1490(3) 0.0831(13) Uani 1 1 d . . . . .
O3 O -0.4635(2) -0.2370(3) -0.3855(3) 0.0717(11) Uani 1 1 d . . . . .
O4 O -0.46328(18) -0.3976(2) -0.45281(19) 0.0475(7) Uani 1 1 d . . . . .
H4 H -0.5174 -0.3885 -0.4810 0.057 Uiso 1 1 d R . . . .
C5 C -0.1814(3) -0.3125(3) -0.3315(3) 0.0404(9) Uani 1 1 d . . . . .
C6 C -0.1390(3) -0.3562(3) -0.2484(3) 0.0387(9) Uani 1 1 d . . . . .
C7 C -0.2735(3) -0.2992(3) -0.3790(2) 0.0373(9) Uani 1 1 d . . . . .
C8 C -0.2835(3) -0.3718(3) -0.2608(3) 0.0360(9) Uani 1 1 d . . . . .
C10 C -0.1908(3) -0.3848(3) -0.2131(2) 0.0377(9) Uani 1 1 d . . . . .
C16 C -0.0379(3) -0.3709(4) -0.1982(3) 0.0464(10) Uani 1 1 d . . . . .
C18 C -0.3252(2) -0.3298(3) -0.3438(3) 0.0356(9) Uani 1 1 d . . . . .
C25 C -0.4265(3) -0.3154(3) -0.3975(3) 0.0423(10) 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
O5 N2 1.203(6) . ?
O6 N2 1.222(6) . ?
N2 C35 1.481(6) . ?
N5 C27 1.355(5) . ?
N5 C30 1.315(6) . ?
N6 C12 1.341(5) . ?
N6 C41 1.328(5) . ?
C9 H9 0.9300 . ?
C9 C30 1.395(8) . ?
C9 C51 1.354(8) . ?
C12 C22 1.415(5) . ?
C12 C27 1.449(5) . ?
C15 H15 0.9300 . ?
C15 C22 1.405(6) . ?
C15 C34 1.343(7) . ?
C19 C27 1.422(6) . ?
C19 C35 1.468(7) . ?
C19 C51 1.392(7) . ?
C22 C32 1.402(6) . ?
C30 H30 0.9300 . ?
C32 H32 0.9300 . ?
C32 C35 1.331(7) . ?
C34 H34 0.9300 . ?
C34 C41 1.384(7) . ?
C41 H41 0.9300 . ?
C51 H51 0.9300 . ?
O7 N1 1.199(5) . ?
O8 N1 1.220(5) . ?
N1 C14 1.470(5) . ?
N3 C26 1.352(5) . ?
N3 C40 1.317(5) . ?
N4 C1 1.320(5) . ?
N4 C17 1.356(5) . ?
C1 H1 0.9300 . ?
C1 C50 1.397(6) . ?
C13 C14 1.443(5) . ?
C13 C26 1.403(5) . ?
C13 C38 1.415(5) . ?
C14 C24 1.342(5) . ?
C17 C21 1.402(5) . ?
C17 C26 1.457(5) . ?
C21 C24 1.429(5) . ?
C21 C33 1.404(5) . ?
C24 H24 0.9300 . ?
C33 H33 0.9300 . ?
C33 C50 1.361(6) . ?
C38 H38 0.9300 . ?
C38 C46 1.360(6) . ?
C40 H40 0.9300 . ?
C40 C46 1.384(6) . ?
C46 H46 0.9300 . ?
C50 H50 0.9300 . ?
Br1 C8 1.892(4) . ?
Br2 C10 1.891(4) . ?
Br3 C5 1.891(4) . ?
Br4 C7 1.886(4) . ?
O1 H1A 0.8201 . ?
O1 C16 1.303(5) . ?
O2 C16 1.199(5) . ?
O3 C25 1.198(5) . ?
O4 H4 0.8140 . ?
O4 C25 1.288(5) . ?
C5 C6 1.387(6) . ?
C5 C7 1.384(5) . ?
C6 C10 1.391(6) . ?
C6 C16 1.518(5) . ?
C7 C18 1.393(5) . ?
C8 C10 1.392(5) . ?
C8 C18 1.379(6) . ?
C18 C25 1.522(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
O5 N2 O6 123.5(5) . . ?
O5 N2 C35 119.5(5) . . ?
O6 N2 C35 116.9(5) . . ?
C30 N5 C27 116.4(4) . . ?
C41 N6 C12 118.3(4) . . ?
C30 C9 H9 120.5 . . ?
C51 C9 H9 120.5 . . ?
C51 C9 C30 118.9(5) . . ?
N6 C12 C22 121.2(4) . . ?
N6 C12 C27 118.9(3) . . ?
C22 C12 C27 120.0(4) . . ?
C22 C15 H15 120.1 . . ?
C34 C15 H15 120.1 . . ?
C34 C15 C22 119.8(4) . . ?
C27 C19 C35 116.4(4) . . ?
C51 C19 C27 115.4(5) . . ?
C51 C19 C35 128.1(4) . . ?
C15 C22 C12 118.0(4) . . ?
C32 C22 C12 119.7(4) . . ?
C32 C22 C15 122.2(4) . . ?
N5 C27 C12 116.2(3) . . ?
N5 C27 C19 124.3(4) . . ?
C19 C27 C12 119.5(4) . . ?
N5 C30 C9 124.0(5) . . ?
N5 C30 H30 118.0 . . ?
C9 C30 H30 118.0 . . ?
C22 C32 H32 119.5 . . ?
C35 C32 C22 121.0(4) . . ?
C35 C32 H32 119.5 . . ?
C15 C34 H34 120.7 . . ?
C15 C34 C41 118.5(4) . . ?
C41 C34 H34 120.7 . . ?
C19 C35 N2 122.5(5) . . ?
C32 C35 N2 114.2(5) . . ?
C32 C35 C19 123.2(4) . . ?
N6 C41 C34 124.1(5) . . ?
N6 C41 H41 118.0 . . ?
C34 C41 H41 118.0 . . ?
C9 C51 C19 120.8(5) . . ?
C9 C51 H51 119.6 . . ?
C19 C51 H51 119.6 . . ?
O7 N1 O8 122.1(4) . . ?
O7 N1 C14 120.0(4) . . ?
O8 N1 C14 117.9(4) . . ?
C40 N3 C26 117.3(4) . . ?
C1 N4 C17 117.9(3) . . ?
N4 C1 H1 118.1 . . ?
N4 C1 C50 123.7(4) . . ?
C50 C1 H1 118.1 . . ?
C26 C13 C14 117.4(3) . . ?
C26 C13 C38 116.7(4) . . ?
C38 C13 C14 125.9(4) . . ?
C13 C14 N1 121.2(3) . . ?
C24 C14 N1 116.1(4) . . ?
C24 C14 C13 122.7(4) . . ?
N4 C17 C21 122.0(3) . . ?
N4 C17 C26 118.5(3) . . ?
C21 C17 C26 119.5(3) . . ?
C17 C21 C24 119.1(3) . . ?
C17 C21 C33 118.6(4) . . ?
C33 C21 C24 122.3(4) . . ?
C14 C24 C21 120.9(4) . . ?
C14 C24 H24 119.5 . . ?
C21 C24 H24 119.5 . . ?
N3 C26 C13 123.4(4) . . ?
N3 C26 C17 116.3(3) . . ?
C13 C26 C17 120.3(3) . . ?
C21 C33 H33 120.7 . . ?
C50 C33 C21 118.7(4) . . ?
C50 C33 H33 120.7 . . ?
C13 C38 H38 120.3 . . ?
C46 C38 C13 119.4(4) . . ?
C46 C38 H38 120.3 . . ?
N3 C40 H40 118.0 . . ?
N3 C40 C46 124.0(4) . . ?
C46 C40 H40 118.0 . . ?
C38 C46 C40 119.2(4) . . ?
C38 C46 H46 120.4 . . ?
C40 C46 H46 120.4 . . ?
C1 C50 H50 120.4 . . ?
C33 C50 C1 119.2(4) . . ?
C33 C50 H50 120.4 . . ?
C16 O1 H1A 109.5 . . ?
C25 O4 H4 110.0 . . ?
C6 C5 Br3 118.1(3) . . ?
C7 C5 Br3 121.2(3) . . ?
C7 C5 C6 120.7(4) . . ?
C5 C6 C10 118.8(4) . . ?
C5 C6 C16 119.6(4) . . ?
C10 C6 C16 121.6(4) . . ?
C5 C7 Br4 120.1(3) . . ?
C5 C7 C18 120.3(4) . . ?
C18 C7 Br4 119.6(3) . . ?
C10 C8 Br1 121.0(3) . . ?
C18 C8 Br1 118.6(3) . . ?
C18 C8 C10 120.3(4) . . ?
C6 C10 Br2 118.3(3) . . ?
C6 C10 C8 120.6(4) . . ?
C8 C10 Br2 121.1(3) . . ?
O1 C16 C6 112.1(3) . . ?
O2 C16 O1 126.3(4) . . ?
O2 C16 C6 121.5(4) . . ?
C7 C18 C25 119.4(4) . . ?
C8 C18 C7 119.3(4) . . ?
C8 C18 C25 121.3(4) . . ?
O3 C25 O4 127.3(4) . . ?
O3 C25 C18 121.5(4) . . ?
O4 C25 C18 111.2(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1016046'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_w1
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C4 H Br2 O2, C4 H4 N2 O2, H2 O'
_chemical_formula_sum            'C8 H7 Br2 N2 O5'
_chemical_formula_weight         370.98
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8320(4)
_cell_length_b                   16.5732(7)
_cell_length_c                   8.9252(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.132(4)
_cell_angle_gamma                90
_cell_volume                     1140.44(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1903
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5350
_cell_measurement_theta_min      3.3760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.119
_exptl_absorpt_correction_T_max  0.9687
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.1079 before and 0.0236 after
correction. The Ratio of minimum to maximum transmission is 0.42976.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.161
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.042 before and 0.029 after
correction. The Ratio of minimum to maximum transmission is 0.684628.
The λ/2 correction factor is 0.0015
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5363
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_min         2.458
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                1928
_reflns_number_total             2365
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.062
_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)+(0.0348P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0762
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C11(H11), C20(H20)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.33505(5) 0.18154(2) 0.48944(5) 0.03654(13) Uani 1 1 d . . . . .
Br2 Br 0.25015(5) 0.06171(2) 0.18757(4) 0.03485(13) Uani 1 1 d . . . . .
O5 O 0.1058(3) 0.02635(15) -0.3260(3) 0.0312(6) Uani 1 1 d . . . . .
C2 C 0.3910(4) 0.0262(2) 0.3687(4) 0.0242(8) Uani 1 1 d . . . . .
C3 C 0.3271(4) -0.1568(2) -0.1904(4) 0.0227(7) Uani 1 1 d . . . . .
N1 N 0.2717(3) -0.20109(17) -0.3235(3) 0.0253(7) Uani 1 1 d . . . . .
H1 H 0.3060 -0.2501 -0.3287 0.030 Uiso 1 1 calc R . . . .
O2 O 0.5194(3) -0.10843(17) 0.1496(3) 0.0330(6) Uani 1 1 d . . . . .
H2A H 0.4928 -0.1438 0.0855 0.049 Uiso 1 1 calc GR . . . .
C6 C 0.4307(4) 0.0772(2) 0.4936(4) 0.0236(8) Uani 1 1 d . . . . .
N2 N 0.1133(3) -0.09540(17) -0.4390(3) 0.0245(6) Uani 1 1 d . . . . .
H2 H 0.0450 -0.0773 -0.5179 0.029 Uiso 1 1 calc R . . . .
C9 C 0.1608(4) -0.0436(2) -0.3138(4) 0.0226(7) Uani 1 1 d . . . . .
O4 O 0.4260(3) -0.19330(14) -0.0852(3) 0.0314(6) Uani 1 1 d . . . . .
C11 C 0.1682(4) -0.1694(2) -0.4408(4) 0.0276(8) Uani 1 1 d . . . . .
H11 H 0.1334 -0.2008 -0.5273 0.033 Uiso 1 1 calc R . . . .
C13 C 0.4592(4) -0.0514(2) 0.3748(4) 0.0239(8) Uani 1 1 d . . . . .
O3 O 0.0956(3) 0.15207(16) -0.1257(3) 0.0383(7) Uani 1 1 d . . . . .
H3A H 0.1270 0.1148 -0.1804 0.058 Uiso 1 1 d G . . . .
H3B H -0.0136 0.1585 -0.1485 0.058 Uiso 1 1 d G . . . .
O1 O 0.2775(3) -0.14716(18) 0.2289(3) 0.0456(7) Uani 1 1 d . . . . .
C18 C 0.4092(4) -0.1081(2) 0.2424(4) 0.0269(8) Uani 1 1 d . . . . .
C20 C 0.2686(4) -0.0783(2) -0.1894(4) 0.0271(8) Uani 1 1 d . . . . .
H20 H 0.3024 -0.0473 -0.1024 0.033 Uiso 1 1 calc R . . . .


_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 1.882(3) . ?
Br2 C2 1.884(3) . ?
O5 C9 1.235(4) . ?
C2 C6 1.390(5) . ?
C2 C13 1.390(5) . ?
C3 N1 1.398(4) . ?
C3 O4 1.262(4) . ?
C3 C20 1.380(5) . ?
N1 C11 1.316(4) . ?
O2 C18 1.297(4) . ?
C6 C13 1.396(5) 3_656 ?
N2 C9 1.406(4) . ?
N2 C11 1.301(4) . ?
C9 C20 1.395(4) . ?
C13 C6 1.396(5) 3_656 ?
C13 C18 1.506(5) . ?
O1 C18 1.205(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
C6 C2 Br2 120.8(3) . . ?
C6 C2 C13 120.1(3) . . ?
C13 C2 Br2 119.0(3) . . ?
O4 C3 N1 116.0(3) . . ?
O4 C3 C20 127.4(3) . . ?
C20 C3 N1 116.5(3) . . ?
C11 N1 C3 121.5(3) . . ?
C2 C6 Br1 120.7(2) . . ?
C2 C6 C13 120.4(3) . 3_656 ?
C13 C6 Br1 118.8(3) 3_656 . ?
C11 N2 C9 122.9(3) . . ?
O5 C9 N2 117.6(3) . . ?
O5 C9 C20 127.6(3) . . ?
C20 C9 N2 114.8(3) . . ?
N2 C11 N1 121.6(3) . . ?
C2 C13 C6 119.5(3) . 3_656 ?
C2 C13 C18 120.1(3) . . ?
C6 C13 C18 120.4(3) 3_656 . ?
O2 C18 C13 113.1(3) . . ?
O1 C18 O2 126.0(3) . . ?
O1 C18 C13 120.9(3) . . ?
C3 C20 C9 122.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1016047'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_w1
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C8 H2 Br4 O4), Br4 C8 O4, 2(C5 H9 N2)'
_chemical_formula_sum            'C34 H22 Br12 N4 O12'
_chemical_formula_weight         1637.36
_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 0.0030 0.0020 '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 -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0669(4)
_cell_length_b                   11.1569(4)
_cell_length_c                   12.8684(4)
_cell_angle_alpha                106.546(3)
_cell_angle_beta                 106.524(4)
_cell_angle_gamma                100.289(4)
_cell_volume                     1147.58(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3545
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4580
_cell_measurement_theta_min      2.4250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.533
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.1079 before and 0.0236 after
correction. The Ratio of minimum to maximum transmission is 0.42976.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             770
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.093 before and 0.032 after
correction. The Ratio of minimum to maximum transmission is 0.5278.
The λ/2 correction factor is 0.0015
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8458
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.443
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                3503
_reflns_number_total             4508
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0164P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0631
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O6(H6), O3(H3), N1(H1), N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Br3 Br 0.77649(6) 0.40714(5) 0.40692(4) 0.04242(14) Uani 1 1 d . . . . .
Br6 Br 0.40446(7) 0.21121(5) 0.30216(4) 0.04537(15) Uani 1 1 d . . . . .
O5 O 0.9240(4) 0.6499(4) 0.6784(2) 0.0566(10) Uani 1 1 d . . . . .
O6 O 0.8678(4) 0.7532(3) 0.5566(2) 0.0432(9) Uani 1 1 d . . . . .
H6 H 0.7928 0.7426 0.4982 0.052 Uiso 1 1 d R . . . .
C9 C 0.6571(5) 0.5809(4) 0.5462(3) 0.0266(10) Uani 1 1 d . . . . .
C14 C 0.4602(6) 0.3792(4) 0.4145(3) 0.0290(11) Uani 1 1 d . . . . .
C15 C 0.6167(5) 0.4596(4) 0.4597(3) 0.0276(10) Uani 1 1 d . . . . .
C26 C 0.8291(6) 0.6651(5) 0.6010(3) 0.0341(11) Uani 1 1 d . . . . .
Br4 Br 1.00544(7) 0.08616(5) -0.22175(3) 0.04382(15) Uani 1 1 d . . . . .
Br5 Br 1.26304(7) -0.06853(5) -0.11981(4) 0.04618(15) Uani 1 1 d . . . . .
O3 O 0.6485(4) 0.0655(3) -0.1637(2) 0.0411(9) Uani 1 1 d . . . . .
H3 H 0.5912 0.1103 -0.1831 0.049 Uiso 1 1 d R . . . .
O4 O 0.8197(4) 0.2591(3) -0.0431(2) 0.0401(8) Uani 1 1 d . . . . .
C6 C 0.8953(5) 0.0666(4) -0.0414(3) 0.0263(10) Uani 1 1 d . . . . .
C7 C 1.1113(5) -0.0288(4) -0.0518(3) 0.0286(10) Uani 1 1 d . . . . .
C10 C 0.7833(6) 0.1406(4) -0.0833(3) 0.0300(11) Uani 1 1 d . . . . .
C11 C 1.0039(5) 0.0360(4) -0.0941(3) 0.0284(11) Uani 1 1 d . . . . .
Br1 Br 0.83561(6) 0.07621(5) 0.45535(4) 0.04020(13) Uani 1 1 d . . . . .
Br2 Br 0.74781(6) 0.29038(4) 0.64981(3) 0.03799(13) Uani 1 1 d . . . . .
O1 O 0.5295(4) -0.1966(3) 0.22823(19) 0.0355(8) Uani 1 1 d . . . . .
O2 O 0.6466(4) -0.2674(3) 0.36465(19) 0.0352(8) Uani 1 1 d . . . . .
C2 C 0.6047(5) 0.1222(4) 0.5624(3) 0.0210(9) Uani 1 1 d . . . . .
C4 C 0.6432(5) 0.0320(4) 0.4826(3) 0.0213(9) Uani 1 1 d . . . . .
C8 C 0.5764(5) -0.1923(4) 0.3316(3) 0.0270(10) Uani 1 1 d . . . . .
C13 C 0.5370(5) -0.0908(4) 0.4194(3) 0.0199(9) Uani 1 1 d . . . . .
N1 N 0.5544(5) 0.4996(3) 0.1716(3) 0.0353(10) Uani 1 1 d . . . . .
H1 H 0.5704 0.5652 0.2324 0.042 Uiso 1 1 d R . . . .
N2 N 0.5972(5) 0.3625(4) 0.0404(3) 0.0421(11) Uani 1 1 d . . . . .
H2 H 0.6452 0.3217 -0.0006 0.050 Uiso 1 1 d R . . . .
C18 C 0.6686(6) 0.4675(4) 0.1346(3) 0.0365(12) Uani 1 1 d . . . . .
C20 C 0.4053(6) 0.4139(4) 0.0995(3) 0.0374(12) Uani 1 1 d . . . . .
C21 C 0.4355(7) 0.3278(4) 0.0175(4) 0.0431(13) Uani 1 1 d . . . . .
H21 H 0.3599 0.2569 -0.0442 0.052 Uiso 1 1 calc R . . . .
C24 C 0.8398(7) 0.5364(5) 0.1875(4) 0.0535(15) Uani 1 1 d . . . . .
H24A H 0.8597 0.6051 0.2591 0.080 Uiso 1 1 calc GR . . . .
H24B H 0.8724 0.5728 0.1357 0.080 Uiso 1 1 calc GR . . . .
H24C H 0.8996 0.4765 0.2026 0.080 Uiso 1 1 calc GR . . . .
C27 C 0.2528(7) 0.4259(5) 0.1162(4) 0.0575(16) Uani 1 1 d . . . . .
H27A H 0.2338 0.5051 0.1078 0.086 Uiso 1 1 calc GR . . . .
H27B H 0.2595 0.4274 0.1924 0.086 Uiso 1 1 calc GR . . . .
H27C H 0.1662 0.3529 0.0591 0.086 Uiso 1 1 calc GR . . . .


_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
Br3 C15 1.881(4) . ?
Br6 C14 1.887(4) . ?
O5 C26 1.193(5) . ?
O6 H6 0.8199 . ?
O6 C26 1.313(5) . ?
C9 C14 1.391(6) 2_666 ?
C9 C15 1.392(5) . ?
C9 C26 1.512(6) . ?
C14 C9 1.391(6) 2_666 ?
C14 C15 1.391(6) . ?
Br4 C11 1.884(4) . ?
Br5 C7 1.880(4) . ?
O3 H3 0.8201 . ?
O3 C10 1.299(5) . ?
O4 C10 1.217(5) . ?
C6 C7 1.392(5) 2_755 ?
C6 C10 1.499(5) . ?
C6 C11 1.384(6) . ?
C7 C6 1.392(5) 2_755 ?
C7 C11 1.393(6) . ?
Br1 C4 1.884(4) . ?
Br2 C2 1.889(4) . ?
O1 C8 1.260(4) . ?
O2 C8 1.236(4) . ?
C2 C4 1.390(5) . ?
C2 C13 1.373(6) 2_656 ?
C4 C13 1.383(5) . ?
C8 C13 1.527(5) . ?
C13 C2 1.373(6) 2_656 ?
N1 H1 0.8600 . ?
N1 C18 1.320(6) . ?
N1 C20 1.387(6) . ?
N2 H2 0.8600 . ?
N2 C18 1.317(5) . ?
N2 C21 1.369(6) . ?
C18 C24 1.462(7) . ?
C20 C21 1.339(6) . ?
C20 C27 1.481(7) . ?
C21 H21 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 O6 H6 109.4 . . ?
C14 C9 C15 119.5(4) 2_666 . ?
C14 C9 C26 120.4(4) 2_666 . ?
C15 C9 C26 120.0(4) . . ?
C9 C14 Br6 118.6(3) 2_666 . ?
C9 C14 C15 120.7(4) 2_666 . ?
C15 C14 Br6 120.6(3) . . ?
C9 C15 Br3 119.0(3) . . ?
C14 C15 Br3 121.2(3) . . ?
C14 C15 C9 119.8(4) . . ?
O5 C26 O6 122.4(4) . . ?
O5 C26 C9 121.4(4) . . ?
O6 C26 C9 116.1(4) . . ?
C10 O3 H3 109.4 . . ?
C7 C6 C10 119.0(4) 2_755 . ?
C11 C6 C7 120.3(4) . 2_755 ?
C11 C6 C10 120.8(4) . . ?
C6 C7 Br5 119.4(3) 2_755 . ?
C6 C7 C11 119.4(4) 2_755 . ?
C11 C7 Br5 121.2(3) . . ?
O3 C10 C6 113.1(4) . . ?
O4 C10 O3 125.5(4) . . ?
O4 C10 C6 121.4(4) . . ?
C6 C11 Br4 118.7(3) . . ?
C6 C11 C7 120.3(4) . . ?
C7 C11 Br4 121.0(3) . . ?
C4 C2 Br2 120.6(3) . . ?
C13 C2 Br2 118.5(3) 2_656 . ?
C13 C2 C4 120.9(4) 2_656 . ?
C2 C4 Br1 120.9(3) . . ?
C13 C4 Br1 119.3(3) . . ?
C13 C4 C2 119.8(4) . . ?
O1 C8 C13 117.1(3) . . ?
O2 C8 O1 124.1(3) . . ?
O2 C8 C13 118.7(3) . . ?
C2 C13 C4 119.3(3) 2_656 . ?
C2 C13 C8 119.7(4) 2_656 . ?
C4 C13 C8 121.0(4) . . ?
C18 N1 H1 124.4 . . ?
C18 N1 C20 111.1(3) . . ?
C20 N1 H1 124.4 . . ?
C18 N2 H2 125.0 . . ?
C18 N2 C21 110.0(4) . . ?
C21 N2 H2 125.0 . . ?
N1 C18 C24 126.5(4) . . ?
N2 C18 N1 106.3(4) . . ?
N2 C18 C24 127.2(5) . . ?
N1 C20 C27 124.1(4) . . ?
C21 C20 N1 104.6(5) . . ?
C21 C20 C27 131.3(5) . . ?
N2 C21 H21 126.0 . . ?
C20 C21 N2 107.9(4) . . ?
C20 C21 H21 126.0 . . ?
C18 C24 H24A 109.5 . . ?
C18 C24 H24B 109.5 . . ?
C18 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C27 H27A 109.5 . . ?
C20 C27 H27B 109.5 . . ?
C20 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1016048'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_w1
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'Br2 C4 O2, C5 H9 N2'
_chemical_formula_sum            'C9 H8 Br2 N2 O2'
_chemical_formula_weight         335.99
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.1803(8)
_cell_length_b                   8.7685(7)
_cell_length_c                   8.9983(10)
_cell_angle_alpha                115.443(10)
_cell_angle_beta                 102.074(9)
_cell_angle_gamma                91.498(8)
_cell_volume                     565.01(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1787
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1560
_cell_measurement_theta_min      2.5770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.155
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.1079 before and 0.0236 after
correction. The Ratio of minimum to maximum transmission is 0.42976.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.082 before and 0.0229 after
correction. The Ratio of minimum to maximum transmission is 0.9377.
The λ/2 correction factor is 0.0015
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3905
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.990
_diffrn_reflns_theta_min         2.568
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                1913
_reflns_number_total             2429
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.063
_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)+(0.0327P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0800
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C17(H17)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.51016(6) 0.72985(4) 0.16383(5) 0.03574(14) Uani 1 1 d . . . . .
Br2 Br 0.43255(6) 1.12789(4) 0.37813(5) 0.03488(14) Uani 1 1 d . . . . .
O1 O 0.5584(4) 1.4569(3) 0.2865(3) 0.0341(7) Uani 1 1 d . . . . .
C4 C 0.4332(5) 1.3496(4) 0.1919(4) 0.0240(8) Uani 1 1 d . . . . .
O2 O 0.2835(4) 1.3747(3) 0.1684(3) 0.0361(7) Uani 1 1 d . . . . .
C6 C 0.4708(4) 1.0525(4) 0.1595(4) 0.0208(7) Uani 1 1 d . . . . .
C7 C 0.5043(5) 0.8872(4) 0.0704(4) 0.0221(8) Uani 1 1 d . . . . .
C8 C 0.4680(4) 1.1676(4) 0.0903(4) 0.0203(7) Uani 1 1 d . . . . .
N2 N 0.8177(4) 1.3578(4) 0.4394(4) 0.0355(8) Uani 1 1 d . . . . .
H2 H 0.7504 1.4055 0.3907 0.043 Uiso 1 1 calc R . . . .
N1 N 0.8367(5) 1.3827(4) 0.5995(5) 0.0370(9) Uani 1 1 d . . . . .
C11 C 0.9511(6) 1.2896(5) 0.6331(5) 0.0420(11) Uani 1 1 d . . . . .
C13 C 0.9192(5) 1.2475(5) 0.3666(5) 0.0372(10) Uani 1 1 d . . . . .
C14 C 0.9233(6) 1.1918(6) 0.1874(6) 0.0569(13) Uani 1 1 d . . . . .
H14A H 0.8812 1.0728 0.1230 0.085 Uiso 1 1 calc GR . . . .
H14B H 1.0372 1.2105 0.1809 0.085 Uiso 1 1 calc GR . . . .
H14C H 0.8541 1.2560 0.1420 0.085 Uiso 1 1 calc GR . . . .
C17 C 1.0062(6) 1.2039(5) 0.4885(6) 0.0464(12) Uani 1 1 d . . . . .
H17 H 1.0874 1.1300 0.4751 0.056 Uiso 1 1 calc R . . . .
C19 C 0.9977(8) 1.2908(7) 0.8024(6) 0.0708(17) Uani 1 1 d . . . . .
H19A H 1.0934 1.3752 0.8727 0.106 Uiso 1 1 calc GR . . . .
H19B H 1.0255 1.1807 0.7892 0.106 Uiso 1 1 calc GR . . . .
H19C H 0.9044 1.3171 0.8545 0.106 Uiso 1 1 calc GR . . . .
H1 H 0.786(5) 1.456(5) 0.672(5) 0.041(12) Uiso 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 C7 1.896(3) . ?
Br2 C6 1.886(3) . ?
O1 C4 1.247(5) . ?
C4 O2 1.240(4) . ?
C4 C8 1.531(4) . ?
C6 C7 1.391(4) . ?
C6 C8 1.394(4) . ?
C7 C8 1.385(5) 2_675 ?
C8 C7 1.385(5) 2_675 ?
N2 N1 1.335(5) . ?
N2 C13 1.333(5) . ?
N1 C11 1.330(5) . ?
C11 C17 1.373(6) . ?
C11 C19 1.486(7) . ?
C13 C14 1.479(6) . ?
C13 C17 1.380(6) . ?

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 C4 C8 116.6(3) . . ?
O2 C4 O1 127.2(3) . . ?
O2 C4 C8 116.2(3) . . ?
C7 C6 Br2 121.0(2) . . ?
C7 C6 C8 120.6(3) . . ?
C8 C6 Br2 118.4(2) . . ?
C6 C7 Br1 121.0(3) . . ?
C8 C7 Br1 118.2(2) 2_675 . ?
C8 C7 C6 120.7(3) 2_675 . ?
C6 C8 C4 119.6(3) . . ?
C7 C8 C4 121.7(3) 2_675 . ?
C7 C8 C6 118.6(3) 2_675 . ?
C13 N2 N1 109.6(3) . . ?
C11 N1 N2 109.3(4) . . ?
N1 C11 C17 107.1(4) . . ?
N1 C11 C19 121.3(4) . . ?
C17 C11 C19 131.6(4) . . ?
N2 C13 C14 122.0(4) . . ?
N2 C13 C17 106.5(4) . . ?
C17 C13 C14 131.4(4) . . ?
C11 C17 C13 107.5(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1016049'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_w1
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H2 Br4 O4, C20 H10 Br4 N4 O4'
_chemical_formula_sum            'C28 H10 Br8 N4 O8'
_chemical_formula_weight         1169.60
_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 0.0030 0.0020 '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 -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8990(5)
_cell_length_b                   9.0236(7)
_cell_length_c                   12.0472(8)
_cell_angle_alpha                105.180(7)
_cell_angle_beta                 109.306(6)
_cell_angle_gamma                96.573(6)
_cell_volume                     859.41(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2200
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2140
_cell_measurement_theta_min      2.5750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.386
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.1079 before and 0.0236 after
correction. The Ratio of minimum to maximum transmission is 0.42976.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             550
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.083 before and 0.042 after
correction. The Ratio of minimum to maximum transmission is 0.5284.
The λ/2 correction factor is 0.0015
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6165
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         2.486
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                2594
_reflns_number_total             3556
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         2.085
_refine_diff_density_min         -1.939
_refine_diff_density_rms         0.280
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3556
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.042
_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)+(0.0841P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1581
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C30(H30), C31(H31), C32(H32)
2.b Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Br2 Br 0.83775(10) 0.78289(10) -0.07903(7) 0.0331(3) Uani 1 1 d . . . . .
Br4 Br 0.66426(10) 0.40755(11) -0.24702(7) 0.0333(3) Uani 1 1 d . . . . .
O3 O 1.2426(8) 0.9103(7) 0.1330(6) 0.0451(17) Uani 1 1 d . . . . .
O4 O 1.0780(7) 0.8676(7) 0.2322(5) 0.0361(15) Uani 1 1 d . . . . .
H4 H 1.1236 0.9577 0.2782 0.054 Uiso 1 1 calc GR . . . .
C7 C 0.8579(8) 0.4631(9) -0.1046(6) 0.0200(16) Uani 1 1 d . . . . .
C9 C 0.9283(9) 0.6194(9) -0.0331(6) 0.0188(15) Uani 1 1 d . . . . .
C12 C 1.0690(9) 0.6548(10) 0.0711(6) 0.0247(18) Uani 1 1 d . . . . .
C24 C 1.1439(10) 0.8269(10) 0.1499(7) 0.0267(18) Uani 1 1 d . . . . .
Br1 Br 0.54928(10) 0.28414(10) 0.38520(8) 0.0328(3) Uani 1 1 d . . . . .
Br3 Br 0.80609(9) 0.04071(11) 0.41055(8) 0.0331(3) Uani 1 1 d . . . . .
O1 O 0.1442(6) 0.1503(7) 0.3717(5) 0.0282(13) Uani 1 1 d . . . . .
O2 O 0.3016(6) 0.3351(7) 0.5509(5) 0.0321(14) Uani 1 1 d . . . . .
C3 C 0.3920(8) 0.1019(8) 0.4888(6) 0.0161(15) Uani 1 1 d . . . . .
C5 C 0.6276(8) 0.0186(9) 0.4613(6) 0.0181(15) Uani 1 1 d . . . . .
C6 C 0.5214(8) 0.1180(8) 0.4485(6) 0.0150(14) Uani 1 1 d . . . . .
C8 C 0.2738(8) 0.2096(9) 0.4727(6) 0.0155(15) Uani 1 1 d . . . . .
N1 N 0.9632(8) 0.3347(9) 0.2972(6) 0.0312(16) Uani 1 1 d . . . . .
N2 N 0.6138(11) 0.7043(13) 0.1042(8) 0.063(3) Uani 1 1 d . . . . .
C13 C 0.7821(10) 0.5235(12) 0.2011(8) 0.033(2) Uani 1 1 d . . . . .
C21 C 1.0102(10) 0.4888(11) 0.3531(7) 0.0313(19) Uani 1 1 d . . . . .
H21 H 1.1045 0.5301 0.4244 0.038 Uiso 1 1 calc R . . . .
C27 C 0.6850(12) 0.6207(13) 0.1455(9) 0.045(2) Uani 1 1 d . . . . .
C30 C 0.9212(10) 0.5870(11) 0.3068(7) 0.033(2) Uani 1 1 d . . . . .
H30 H 0.9538 0.6953 0.3460 0.039 Uiso 1 1 calc R . . . .
C31 C 0.8279(11) 0.2743(12) 0.1955(8) 0.042(2) Uani 1 1 d . . . . .
H31 H 0.7982 0.1657 0.1579 0.050 Uiso 1 1 calc R . . . .
C32 C 0.7315(10) 0.3636(12) 0.1443(8) 0.041(2) Uani 1 1 d . . . . .
H32 H 0.6360 0.3190 0.0743 0.050 Uiso 1 1 calc R . . . .
H1 H 1.064(10) 0.272(11) 0.342(7) 0.04(2) Uiso 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
Br2 C9 1.880(7) . ?
Br4 C7 1.887(7) . ?
O3 C24 1.194(10) . ?
O4 H4 0.8200 . ?
O4 C24 1.306(9) . ?
C7 C9 1.389(10) . ?
C7 C12 1.389(11) 2_765 ?
C9 C12 1.381(10) . ?
C12 C7 1.389(11) 2_765 ?
C12 C24 1.526(11) . ?
Br1 C6 1.879(7) . ?
Br3 C5 1.890(7) . ?
O1 C8 1.299(8) . ?
O2 C8 1.206(8) . ?
C3 C5 1.393(10) 2_656 ?
C3 C6 1.396(10) . ?
C3 C8 1.512(9) . ?
C5 C3 1.393(10) 2_656 ?
C5 C6 1.375(10) . ?
N1 C21 1.323(11) . ?
N1 C31 1.331(11) . ?
N1 H1 1.17(9) . ?
N2 C27 1.147(12) . ?
C13 C27 1.437(13) . ?
C13 C30 1.377(12) . ?
C13 C32 1.372(14) . ?
C21 H21 0.9300 . ?
C21 C30 1.361(12) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.355(13) . ?
C32 H32 0.9300 . ?

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
C24 O4 H4 109.5 . . ?
C9 C7 Br4 121.2(6) . . ?
C12 C7 Br4 119.2(5) 2_765 . ?
C12 C7 C9 119.6(7) 2_765 . ?
C7 C9 Br2 120.9(5) . . ?
C12 C9 Br2 119.8(6) . . ?
C12 C9 C7 119.3(7) . . ?
C7 C12 C24 120.1(7) 2_765 . ?
C9 C12 C7 121.1(7) . 2_765 ?
C9 C12 C24 118.8(7) . . ?
O3 C24 O4 126.6(8) . . ?
O3 C24 C12 123.7(7) . . ?
O4 C24 C12 109.6(7) . . ?
C5 C3 C6 118.3(6) 2_656 . ?
C5 C3 C8 121.8(6) 2_656 . ?
C6 C3 C8 119.8(6) . . ?
C3 C5 Br3 117.5(5) 2_656 . ?
C6 C5 Br3 120.7(6) . . ?
C6 C5 C3 121.8(6) . 2_656 ?
C3 C6 Br1 117.7(5) . . ?
C5 C6 Br1 122.2(5) . . ?
C5 C6 C3 119.9(7) . . ?
O1 C8 C3 113.4(6) . . ?
O2 C8 O1 126.0(7) . . ?
O2 C8 C3 120.6(6) . . ?
C21 N1 C31 120.3(8) . . ?
C21 N1 H1 110(4) . . ?
C31 N1 H1 129(4) . . ?
C30 C13 C27 121.8(9) . . ?
C32 C13 C27 117.4(8) . . ?
C32 C13 C30 120.9(8) . . ?
N1 C21 H21 119.8 . . ?
N1 C21 C30 120.3(8) . . ?
C30 C21 H21 119.8 . . ?
N2 C27 C13 176.7(13) . . ?
C13 C30 H30 120.5 . . ?
C21 C30 C13 118.9(9) . . ?
C21 C30 H30 120.5 . . ?
N1 C31 H31 118.5 . . ?
N1 C31 C32 123.1(10) . . ?
C32 C31 H31 118.5 . . ?
C13 C32 H32 121.8 . . ?
C31 C32 C13 116.5(8) . . ?
C31 C32 H32 121.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1016050'
