# 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.
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data_mo_dm13008_0m
#TrackingRef 'mo_dm13008_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Br N O4'
_chemical_formula_weight         340.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   6.2427(12)
_cell_length_b                   19.473(4)
_cell_length_c                   11.986(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.370(3)
_cell_angle_gamma                90.00
_cell_volume                     1411.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    4821
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      30.13

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4741
_exptl_absorpt_correction_T_max  0.8920
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13762
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0683
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         30.60
_reflns_number_total             6804
_reflns_number_gt                5512
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0295P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6804
_refine_ls_number_parameters     361
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.45960(7) 1.132859(19) 1.24708(3) 0.04794(11) Uani 1 1 d . . .
Br2 Br -0.15054(8) 0.364215(18) 0.77979(3) 0.05137(12) Uani 1 1 d . . .
N1 N -0.0477(5) 0.95125(13) 0.9433(2) 0.0278(5) Uani 1 1 d . . .
H1 H -0.0812 0.9074 0.9441 0.033 Uiso 1 1 calc R . .
N2 N 0.1530(5) 0.55929(13) 0.4549(2) 0.0286(5) Uani 1 1 d . . .
H2 H 0.0942 0.6005 0.4520 0.034 Uiso 1 1 calc R . .
O1 O -0.1116(4) 0.68311(14) 0.4622(2) 0.0446(6) Uani 1 1 d . . .
O2 O -0.1488(5) 0.74278(18) 0.6135(3) 0.0651(9) Uani 1 1 d . . .
O3 O 0.1529(4) 0.91387(10) 0.82771(16) 0.0273(4) Uani 1 1 d . . .
O4 O 0.1420(5) 1.02773(11) 0.8593(2) 0.0413(6) Uani 1 1 d . . .
O5 O 0.7811(3) 0.80567(11) -0.05755(19) 0.0305(5) Uani 1 1 d . . .
O6 O 0.9102(3) 0.72367(11) 0.07223(19) 0.0277(4) Uani 1 1 d . . .
O7 O 0.3194(3) 0.60733(10) 0.33308(16) 0.0259(4) Uani 1 1 d . . .
O8 O 0.3790(4) 0.49429(12) 0.3724(2) 0.0385(6) Uani 1 1 d . . .
C1 C -0.0458(6) 0.72862(19) 0.5311(3) 0.0353(7) Uani 1 1 d . . .
C2 C 0.1466(6) 0.77384(18) 0.5425(3) 0.0343(7) Uani 1 1 d . . .
C3 C 0.1245(6) 0.83127(18) 0.6228(3) 0.0364(7) Uani 1 1 d . . .
H3 H 0.0403 0.8694 0.5755 0.044 Uiso 1 1 calc R . .
C4 C -0.0296(7) 0.7967(3) 0.6891(4) 0.0586(13) Uani 1 1 d . . .
H4A H 0.0578 0.7767 0.7622 0.070 Uiso 1 1 calc R . .
H4B H -0.1345 0.8306 0.7069 0.070 Uiso 1 1 calc R . .
C5 C 0.3009(7) 0.7639(2) 0.4847(3) 0.0445(9) Uani 1 1 d . . .
H5A H 0.2891 0.7261 0.4334 0.053 Uiso 1 1 calc R . .
H5B H 0.4226 0.7945 0.4949 0.053 Uiso 1 1 calc R . .
C6 C 0.3343(5) 0.86081(18) 0.6960(3) 0.0320(6) Uani 1 1 d . . .
H6A H 0.4390 0.8687 0.6473 0.038 Uiso 1 1 calc R . .
H6B H 0.4022 0.8268 0.7558 0.038 Uiso 1 1 calc R . .
C7 C 0.3020(6) 0.92733(16) 0.7540(3) 0.0313(6) Uani 1 1 d . . .
H7A H 0.4457 0.9445 0.8005 0.038 Uiso 1 1 calc R . .
H7B H 0.2376 0.9625 0.6956 0.038 Uiso 1 1 calc R . .
C8 C 0.0855(5) 0.96997(15) 0.8752(2) 0.0256(6) Uani 1 1 d . . .
C9 C -0.1385(5) 0.99523(15) 1.0133(2) 0.0242(6) Uani 1 1 d . . .
C10 C -0.0522(6) 1.05947(17) 1.0481(3) 0.0325(7) Uani 1 1 d . . .
H10 H 0.0716 1.0760 1.0234 0.039 Uiso 1 1 calc R . .
C11 C -0.1459(6) 1.09964(18) 1.1188(3) 0.0362(7) Uani 1 1 d . . .
H11 H -0.0850 1.1434 1.1437 0.043 Uiso 1 1 calc R . .
C12 C -0.3276(6) 1.07597(18) 1.1527(2) 0.0327(7) Uani 1 1 d . . .
C13 C -0.4174(6) 1.01297(18) 1.1190(3) 0.0334(7) Uani 1 1 d . . .
H13 H -0.5428 0.9972 1.1431 0.040 Uiso 1 1 calc R . .
C14 C -0.3223(6) 0.97251(16) 1.0489(3) 0.0290(6) Uani 1 1 d . . .
H14 H -0.3835 0.9287 1.0250 0.035 Uiso 1 1 calc R . .
C15 C 0.5368(5) 0.74471(15) 0.0379(2) 0.0238(6) Uani 1 1 d . . .
C16 C 0.7461(4) 0.76351(15) 0.0092(2) 0.0229(6) Uani 1 1 d . . .
C17 C 0.5805(5) 0.68121(14) 0.1103(2) 0.0213(5) Uani 1 1 d . . .
H17 H 0.5489 0.6402 0.0587 0.026 Uiso 1 1 calc R . .
C18 C 0.8294(5) 0.68654(15) 0.1597(2) 0.0250(6) Uani 1 1 d . . .
H18A H 0.8638 0.7121 0.2334 0.030 Uiso 1 1 calc R . .
H18B H 0.8972 0.6403 0.1730 0.030 Uiso 1 1 calc R . .
C19 C 0.3551(5) 0.78303(17) 0.0034(3) 0.0317(7) Uani 1 1 d . . .
H19A H 0.3585 0.8234 -0.0406 0.038 Uiso 1 1 calc R . .
H19B H 0.2223 0.7699 0.0229 0.038 Uiso 1 1 calc R . .
C20 C 0.4458(5) 0.67537(16) 0.2008(3) 0.0269(6) Uani 1 1 d . . .
H20A H 0.4986 0.7103 0.2615 0.032 Uiso 1 1 calc R . .
H20B H 0.2886 0.6852 0.1640 0.032 Uiso 1 1 calc R . .
C21 C 0.4637(5) 0.60483(16) 0.2559(2) 0.0247(6) Uani 1 1 d . . .
H21A H 0.4153 0.5688 0.1968 0.030 Uiso 1 1 calc R . .
H21B H 0.6179 0.5952 0.2988 0.030 Uiso 1 1 calc R . .
C22 C 0.2919(5) 0.54775(15) 0.3859(2) 0.0245(6) Uani 1 1 d . . .
C23 C 0.0936(5) 0.51181(16) 0.5308(2) 0.0254(6) Uani 1 1 d . . .
C24 C -0.0965(6) 0.52710(19) 0.5688(3) 0.0351(7) Uani 1 1 d . . .
H24 H -0.1784 0.5675 0.5423 0.042 Uiso 1 1 calc R . .
C25 C -0.1646(6) 0.4842(2) 0.6437(3) 0.0368(8) Uani 1 1 d . . .
H25 H -0.2917 0.4953 0.6702 0.044 Uiso 1 1 calc R . .
C26 C -0.0473(6) 0.42460(18) 0.6806(3) 0.0360(8) Uani 1 1 d . . .
C27 C 0.1422(6) 0.40882(18) 0.6463(3) 0.0367(8) Uani 1 1 d . . .
H27 H 0.2239 0.3685 0.6738 0.044 Uiso 1 1 calc R . .
C28 C 0.2127(6) 0.45322(16) 0.5701(3) 0.0294(7) Uani 1 1 d . . .
H28 H 0.3427 0.4429 0.5457 0.035 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 C12 1.910(3) . ?
Br2 C26 1.895(3) . ?
N1 C8 1.352(4) . ?
N1 C9 1.412(4) . ?
N1 H1 0.8800 . ?
N2 C22 1.358(4) . ?
N2 C23 1.410(4) . ?
N2 H2 0.8800 . ?
O1 C1 1.211(4) . ?
O2 C1 1.334(4) . ?
O2 C4 1.463(5) . ?
O3 C8 1.347(3) . ?
O3 C7 1.458(4) . ?
O4 C8 1.208(4) . ?
O5 C16 1.203(3) . ?
O6 C16 1.356(4) . ?
O6 C18 1.462(3) . ?
O7 C22 1.353(3) . ?
O7 C21 1.443(3) . ?
O8 C22 1.203(4) . ?
C1 C2 1.468(5) . ?
C2 C5 1.333(5) . ?
C2 C3 1.504(4) . ?
C3 C6 1.499(5) . ?
C3 C4 1.547(6) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C6 C7 1.507(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.385(5) . ?
C9 C14 1.392(4) . ?
C10 C11 1.385(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.368(5) . ?
C13 C14 1.388(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C19 1.335(4) . ?
C15 C16 1.477(4) . ?
C15 C17 1.497(4) . ?
C17 C18 1.523(4) . ?
C17 C20 1.533(4) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?
C20 C21 1.516(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 C28 1.379(5) . ?
C23 C24 1.404(4) . ?
C24 C25 1.369(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.381(5) . ?
C27 C28 1.405(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C9 126.3(2) . . ?
C8 N1 H1 116.8 . . ?
C9 N1 H1 116.8 . . ?
C22 N2 C23 126.5(3) . . ?
C22 N2 H2 116.7 . . ?
C23 N2 H2 116.7 . . ?
C1 O2 C4 110.0(3) . . ?
C8 O3 C7 115.1(2) . . ?
C16 O6 C18 109.6(2) . . ?
C22 O7 C21 116.3(2) . . ?
O1 C1 O2 120.8(3) . . ?
O1 C1 C2 129.3(3) . . ?
O2 C1 C2 109.9(3) . . ?
C5 C2 C1 123.0(3) . . ?
C5 C2 C3 129.3(4) . . ?
C1 C2 C3 107.6(3) . . ?
C6 C3 C2 117.0(3) . . ?
C6 C3 C4 115.5(3) . . ?
C2 C3 C4 99.9(3) . . ?
C6 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
C4 C3 H3 107.9 . . ?
O2 C4 C3 106.3(3) . . ?
O2 C4 H4A 110.5 . . ?
C3 C4 H4A 110.5 . . ?
O2 C4 H4B 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C2 C5 H5A 120.0 . . ?
C2 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
C3 C6 C7 113.7(3) . . ?
C3 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
C3 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O3 C7 C6 107.7(2) . . ?
O3 C7 H7A 110.2 . . ?
C6 C7 H7A 110.2 . . ?
O3 C7 H7B 110.2 . . ?
C6 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
O4 C8 O3 123.7(3) . . ?
O4 C8 N1 126.4(3) . . ?
O3 C8 N1 109.9(2) . . ?
C10 C9 C14 118.9(3) . . ?
C10 C9 N1 122.9(3) . . ?
C14 C9 N1 118.2(3) . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 Br1 119.3(3) . . ?
C11 C12 Br1 119.3(3) . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C9 120.9(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C19 C15 C16 121.5(3) . . ?
C19 C15 C17 131.3(3) . . ?
C16 C15 C17 107.2(2) . . ?
O5 C16 O6 121.6(2) . . ?
O5 C16 C15 129.9(3) . . ?
O6 C16 C15 108.5(2) . . ?
C15 C17 C18 101.0(2) . . ?
C15 C17 C20 114.8(2) . . ?
C18 C17 C20 114.6(2) . . ?
C15 C17 H17 108.7 . . ?
C18 C17 H17 108.7 . . ?
C20 C17 H17 108.7 . . ?
O6 C18 C17 104.8(2) . . ?
O6 C18 H18A 110.8 . . ?
C17 C18 H18A 110.8 . . ?
O6 C18 H18B 110.8 . . ?
C17 C18 H18B 110.8 . . ?
H18A C18 H18B 108.9 . . ?
C15 C19 H19A 120.0 . . ?
C15 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C21 C20 C17 112.4(2) . . ?
C21 C20 H20A 109.1 . . ?
C17 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C17 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
O7 C21 C20 105.0(2) . . ?
O7 C21 H21A 110.8 . . ?
C20 C21 H21A 110.8 . . ?
O7 C21 H21B 110.8 . . ?
C20 C21 H21B 110.8 . . ?
H21A C21 H21B 108.8 . . ?
O8 C22 O7 124.4(2) . . ?
O8 C22 N2 127.1(3) . . ?
O7 C22 N2 108.5(2) . . ?
C28 C23 C24 119.5(3) . . ?
C28 C23 N2 123.9(3) . . ?
C24 C23 N2 116.7(3) . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 121.0(3) . . ?
C27 C26 Br2 119.9(3) . . ?
C25 C26 Br2 119.1(3) . . ?
C26 C27 C28 119.1(3) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C23 C28 C27 120.1(3) . . ?
C23 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O2 C1 O1 176.5(4) . . . . ?
C4 O2 C1 C2 -2.1(4) . . . . ?
O1 C1 C2 C5 -10.1(6) . . . . ?
O2 C1 C2 C5 168.4(4) . . . . ?
O1 C1 C2 C3 167.1(3) . . . . ?
O2 C1 C2 C3 -14.4(4) . . . . ?
C5 C2 C3 C6 -34.6(5) . . . . ?
C1 C2 C3 C6 148.4(3) . . . . ?
C5 C2 C3 C4 -160.1(4) . . . . ?
C1 C2 C3 C4 22.9(4) . . . . ?
C1 O2 C4 C3 17.2(5) . . . . ?
C6 C3 C4 O2 -150.4(3) . . . . ?
C2 C3 C4 O2 -23.9(4) . . . . ?
C2 C3 C6 C7 167.3(3) . . . . ?
C4 C3 C6 C7 -75.5(4) . . . . ?
C8 O3 C7 C6 -172.3(2) . . . . ?
C3 C6 C7 O3 60.2(3) . . . . ?
C7 O3 C8 O4 0.0(4) . . . . ?
C7 O3 C8 N1 -178.8(2) . . . . ?
C9 N1 C8 O4 -3.2(5) . . . . ?
C9 N1 C8 O3 175.5(3) . . . . ?
C8 N1 C9 C10 -19.9(5) . . . . ?
C8 N1 C9 C14 160.3(3) . . . . ?
C14 C9 C10 C11 1.1(5) . . . . ?
N1 C9 C10 C11 -178.7(3) . . . . ?
C9 C10 C11 C12 -1.1(5) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C10 C11 C12 Br1 -178.5(2) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
Br1 C12 C13 C14 179.0(2) . . . . ?
C12 C13 C14 C9 0.0(5) . . . . ?
C10 C9 C14 C13 -0.5(5) . . . . ?
N1 C9 C14 C13 179.2(3) . . . . ?
C18 O6 C16 O5 169.9(3) . . . . ?
C18 O6 C16 C15 -10.5(3) . . . . ?
C19 C15 C16 O5 -11.7(5) . . . . ?
C17 C15 C16 O5 170.3(3) . . . . ?
C19 C15 C16 O6 168.7(3) . . . . ?
C17 C15 C16 O6 -9.3(3) . . . . ?
C19 C15 C17 C18 -154.1(3) . . . . ?
C16 C15 C17 C18 23.7(3) . . . . ?
C19 C15 C17 C20 -30.2(4) . . . . ?
C16 C15 C17 C20 147.5(3) . . . . ?
C16 O6 C18 C17 25.8(3) . . . . ?
C15 C17 C18 O6 -29.3(3) . . . . ?
C20 C17 C18 O6 -153.2(2) . . . . ?
C15 C17 C20 C21 169.2(2) . . . . ?
C18 C17 C20 C21 -74.5(3) . . . . ?
C22 O7 C21 C20 174.5(2) . . . . ?
C17 C20 C21 O7 -177.0(2) . . . . ?
C21 O7 C22 O8 0.1(4) . . . . ?
C21 O7 C22 N2 179.8(2) . . . . ?
C23 N2 C22 O8 4.4(5) . . . . ?
C23 N2 C22 O7 -175.3(3) . . . . ?
C22 N2 C23 C28 18.9(5) . . . . ?
C22 N2 C23 C24 -162.3(3) . . . . ?
C28 C23 C24 C25 -0.4(5) . . . . ?
N2 C23 C24 C25 -179.2(3) . . . . ?
C23 C24 C25 C26 -1.2(5) . . . . ?
C24 C25 C26 C27 2.3(5) . . . . ?
C24 C25 C26 Br2 -177.7(2) . . . . ?
C25 C26 C27 C28 -1.8(5) . . . . ?
Br2 C26 C27 C28 178.2(2) . . . . ?
C24 C23 C28 C27 0.9(4) . . . . ?
N2 C23 C28 C27 179.6(3) . . . . ?
C26 C27 C28 C23 0.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        30.60
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 934198'
#######################################################################
#
#                 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_mo_dm13009_0m
#TrackingRef 'mo_dm13009_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Br N O4'
_chemical_formula_weight         340.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   6.2368(15)
_cell_length_b                   19.469(5)
_cell_length_c                   11.972(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.381(4)
_cell_angle_gamma                90.00
_cell_volume                     1408.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    2681
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      23.07

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4734
_exptl_absorpt_correction_T_max  0.8918
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13779
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.1051
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         30.62
_reflns_number_total             6929
_reflns_number_gt                4445
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6929
_refine_ls_number_parameters     361
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.46113(9) -0.13256(3) -0.24682(4) 0.05021(15) Uani 1 1 d . . .
Br2 Br 1.14903(9) 0.63560(2) 0.21954(4) 0.05224(16) Uani 1 1 d . . .
N1 N 0.0492(6) 0.04869(16) 0.0575(3) 0.0283(7) Uani 1 1 d . . .
H1 H 0.0836 0.0925 0.0575 0.034 Uiso 1 1 calc R . .
N2 N 0.8456(5) 0.44087(17) 0.5450(3) 0.0276(7) Uani 1 1 d . . .
H2 H 0.9039 0.3996 0.5480 0.033 Uiso 1 1 calc R . .
O1 O 0.1113(5) 0.31675(16) 0.5385(3) 0.0438(8) Uani 1 1 d . . .
O2 O 0.1499(6) 0.2560(2) 0.3878(3) 0.0703(13) Uani 1 1 d . . .
O3 O -0.1522(5) 0.08602(13) 0.1724(2) 0.0291(6) Uani 1 1 d . . .
O4 O -0.1415(6) -0.02795(14) 0.1408(3) 0.0420(8) Uani 1 1 d . . .
O5 O 0.2205(4) 0.19418(14) 1.0590(2) 0.0316(6) Uani 1 1 d . . .
O6 O 0.0904(4) 0.27643(14) 0.9291(2) 0.0287(6) Uani 1 1 d . . .
O7 O 0.6806(4) 0.39263(13) 0.6667(2) 0.0275(6) Uani 1 1 d . . .
O8 O 0.6189(5) 0.50523(15) 0.6266(3) 0.0385(7) Uani 1 1 d . . .
C1 C 0.0459(7) 0.2716(2) 0.4692(4) 0.0359(10) Uani 1 1 d . . .
C2 C -0.1467(8) 0.2264(2) 0.4579(4) 0.0384(10) Uani 1 1 d . . .
C3 C -0.1247(8) 0.1691(2) 0.3767(4) 0.0392(11) Uani 1 1 d . . .
H3 H -0.0402 0.1311 0.4243 0.047 Uiso 1 1 calc R . .
C4 C 0.0300(9) 0.2029(3) 0.3114(5) 0.0605(17) Uani 1 1 d . . .
H4A H 0.1342 0.1687 0.2935 0.073 Uiso 1 1 calc R . .
H4B H -0.0562 0.2234 0.2383 0.073 Uiso 1 1 calc R . .
C5 C -0.2978(9) 0.2355(2) 0.5164(4) 0.0425(11) Uani 1 1 d . . .
H5A H -0.2848 0.2728 0.5689 0.051 Uiso 1 1 calc R . .
H5B H -0.4195 0.2048 0.5061 0.051 Uiso 1 1 calc R . .
C6 C -0.3338(7) 0.1388(2) 0.3040(3) 0.0346(9) Uani 1 1 d . . .
H6A H -0.4027 0.1724 0.2438 0.042 Uiso 1 1 calc R . .
H6B H -0.4380 0.1310 0.3531 0.042 Uiso 1 1 calc R . .
C7 C -0.3020(7) 0.0724(2) 0.2468(4) 0.0344(10) Uani 1 1 d . . .
H7A H -0.2372 0.0374 0.3055 0.041 Uiso 1 1 calc R . .
H7B H -0.4459 0.0551 0.2004 0.041 Uiso 1 1 calc R . .
C8 C -0.0854(7) 0.0296(2) 0.1244(3) 0.0284(9) Uani 1 1 d . . .
C9 C 0.1394(6) 0.0048(2) -0.0125(3) 0.0258(8) Uani 1 1 d . . .
C10 C 0.0535(7) -0.0596(2) -0.0485(3) 0.0322(9) Uani 1 1 d . . .
H10 H -0.0718 -0.0761 -0.0250 0.039 Uiso 1 1 calc R . .
C11 C 0.1487(7) -0.0999(2) -0.1182(4) 0.0362(10) Uani 1 1 d . . .
H11 H 0.0891 -0.1439 -0.1429 0.043 Uiso 1 1 calc R . .
C12 C 0.3305(7) -0.0758(2) -0.1514(3) 0.0347(10) Uani 1 1 d . . .
C13 C 0.4181(8) -0.0127(2) -0.1182(4) 0.0344(10) Uani 1 1 d . . .
H13 H 0.5424 0.0034 -0.1431 0.041 Uiso 1 1 calc R . .
C14 C 0.3240(7) 0.0277(2) -0.0478(3) 0.0307(9) Uani 1 1 d . . .
H14 H 0.3858 0.0714 -0.0234 0.037 Uiso 1 1 calc R . .
C15 C 0.4646(6) 0.2552(2) 0.9625(3) 0.0261(9) Uani 1 1 d . . .
C16 C 0.2535(6) 0.23678(19) 0.9909(3) 0.0251(8) Uani 1 1 d . . .
C17 C 0.4188(6) 0.3186(2) 0.8892(3) 0.0228(8) Uani 1 1 d . . .
H17 H 0.4502 0.3597 0.9407 0.027 Uiso 1 1 calc R . .
C18 C 0.1700(6) 0.31309(19) 0.8402(3) 0.0260(8) Uani 1 1 d . . .
H18A H 0.1018 0.3592 0.8262 0.031 Uiso 1 1 calc R . .
H18B H 0.1353 0.2871 0.7668 0.031 Uiso 1 1 calc R . .
C19 C 0.6430(7) 0.2170(2) 0.9960(4) 0.0331(9) Uani 1 1 d . . .
H19A H 0.6387 0.1764 1.0395 0.040 Uiso 1 1 calc R . .
H19B H 0.7761 0.2299 0.9766 0.040 Uiso 1 1 calc R . .
C20 C 0.5528(7) 0.3245(2) 0.7986(3) 0.0274(9) Uani 1 1 d . . .
H20A H 0.7099 0.3139 0.8350 0.033 Uiso 1 1 calc R . .
H20B H 0.4983 0.2900 0.7373 0.033 Uiso 1 1 calc R . .
C21 C 0.5376(6) 0.3954(2) 0.7445(3) 0.0253(8) Uani 1 1 d . . .
H21A H 0.3834 0.4058 0.7021 0.030 Uiso 1 1 calc R . .
H21B H 0.5884 0.4310 0.8042 0.030 Uiso 1 1 calc R . .
C22 C 0.7062(6) 0.45228(19) 0.6133(3) 0.0237(8) Uani 1 1 d . . .
C23 C 0.9077(7) 0.4885(2) 0.4692(3) 0.0268(9) Uani 1 1 d . . .
C24 C 1.0960(7) 0.4726(2) 0.4319(4) 0.0355(10) Uani 1 1 d . . .
H24 H 1.1774 0.4320 0.4580 0.043 Uiso 1 1 calc R . .
C25 C 1.1637(7) 0.5163(2) 0.3568(3) 0.0378(11) Uani 1 1 d . . .
H25 H 1.2926 0.5057 0.3314 0.045 Uiso 1 1 calc R . .
C26 C 1.0459(8) 0.5750(2) 0.3184(3) 0.0365(11) Uani 1 1 d . . .
C27 C 0.8563(8) 0.5909(2) 0.3535(3) 0.0357(10) Uani 1 1 d . . .
H27 H 0.7744 0.6313 0.3265 0.043 Uiso 1 1 calc R . .
C28 C 0.7875(7) 0.5466(2) 0.4294(3) 0.0309(10) Uani 1 1 d . . .
H28 H 0.6569 0.5566 0.4536 0.037 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 C12 1.911(4) . ?
Br2 C26 1.892(4) . ?
N1 C8 1.348(5) . ?
N1 C9 1.408(5) . ?
N1 H1 0.8800 . ?
N2 C22 1.352(5) . ?
N2 C23 1.417(5) . ?
N2 H2 0.8800 . ?
O1 C1 1.208(5) . ?
O2 C1 1.333(5) . ?
O2 C4 1.458(6) . ?
O3 C8 1.353(5) . ?
O3 C7 1.466(5) . ?
O4 C8 1.204(5) . ?
O5 C16 1.216(4) . ?
O6 C16 1.344(5) . ?
O6 C18 1.466(4) . ?
O7 C22 1.354(4) . ?
O7 C21 1.442(4) . ?
O8 C22 1.195(5) . ?
C1 C2 1.468(7) . ?
C2 C5 1.318(6) . ?
C2 C3 1.508(6) . ?
C3 C6 1.497(6) . ?
C3 C4 1.534(7) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C6 C7 1.499(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.391(6) . ?
C9 C14 1.394(6) . ?
C10 C11 1.382(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.362(6) . ?
C13 C14 1.386(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C19 1.315(5) . ?
C15 C16 1.483(5) . ?
C15 C17 1.500(5) . ?
C17 C18 1.520(5) . ?
C17 C20 1.530(5) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?
C20 C21 1.519(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 C28 1.376(6) . ?
C23 C24 1.391(6) . ?
C24 C25 1.378(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.376(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.385(6) . ?
C27 C28 1.395(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C9 125.9(3) . . ?
C8 N1 H1 117.1 . . ?
C9 N1 H1 117.1 . . ?
C22 N2 C23 126.8(3) . . ?
C22 N2 H2 116.6 . . ?
C23 N2 H2 116.6 . . ?
C1 O2 C4 110.7(4) . . ?
C8 O3 C7 114.9(3) . . ?
C16 O6 C18 109.5(3) . . ?
C22 O7 C21 115.9(3) . . ?
O1 C1 O2 121.7(4) . . ?
O1 C1 C2 129.0(4) . . ?
O2 C1 C2 109.4(4) . . ?
C5 C2 C1 123.1(5) . . ?
C5 C2 C3 129.3(5) . . ?
C1 C2 C3 107.5(4) . . ?
C6 C3 C2 117.4(4) . . ?
C6 C3 C4 116.1(4) . . ?
C2 C3 C4 100.4(4) . . ?
C6 C3 H3 107.4 . . ?
C2 C3 H3 107.4 . . ?
C4 C3 H3 107.4 . . ?
O2 C4 C3 105.9(4) . . ?
O2 C4 H4A 110.6 . . ?
C3 C4 H4A 110.6 . . ?
O2 C4 H4B 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
C2 C5 H5A 120.0 . . ?
C2 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
C3 C6 C7 114.2(4) . . ?
C3 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C3 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
O3 C7 C6 107.3(3) . . ?
O3 C7 H7A 110.2 . . ?
C6 C7 H7A 110.2 . . ?
O3 C7 H7B 110.2 . . ?
C6 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
O4 C8 N1 127.1(4) . . ?
O4 C8 O3 123.6(4) . . ?
N1 C8 O3 109.3(3) . . ?
C10 C9 C14 118.5(4) . . ?
C10 C9 N1 123.5(4) . . ?
C14 C9 N1 118.0(4) . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 119.3(4) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 121.6(4) . . ?
C13 C12 Br1 119.8(3) . . ?
C11 C12 Br1 118.7(4) . . ?
C12 C13 C14 119.3(4) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C9 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C19 C15 C16 121.7(4) . . ?
C19 C15 C17 131.9(3) . . ?
C16 C15 C17 106.4(3) . . ?
O5 C16 O6 122.1(3) . . ?
O5 C16 C15 128.8(4) . . ?
O6 C16 C15 109.2(3) . . ?
C15 C17 C18 101.3(3) . . ?
C15 C17 C20 114.7(3) . . ?
C18 C17 C20 114.6(3) . . ?
C15 C17 H17 108.6 . . ?
C18 C17 H17 108.6 . . ?
C20 C17 H17 108.6 . . ?
O6 C18 C17 104.5(3) . . ?
O6 C18 H18A 110.8 . . ?
C17 C18 H18A 110.8 . . ?
O6 C18 H18B 110.8 . . ?
C17 C18 H18B 110.8 . . ?
H18A C18 H18B 108.9 . . ?
C15 C19 H19A 120.0 . . ?
C15 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C21 C20 C17 112.5(3) . . ?
C21 C20 H20A 109.1 . . ?
C17 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C17 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
O7 C21 C20 105.0(3) . . ?
O7 C21 H21A 110.8 . . ?
C20 C21 H21A 110.8 . . ?
O7 C21 H21B 110.8 . . ?
C20 C21 H21B 110.8 . . ?
H21A C21 H21B 108.8 . . ?
O8 C22 N2 127.2(3) . . ?
O8 C22 O7 124.5(3) . . ?
N2 C22 O7 108.3(3) . . ?
C28 C23 C24 120.2(4) . . ?
C28 C23 N2 123.2(4) . . ?
C24 C23 N2 116.6(4) . . ?
C25 C24 C23 119.5(4) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C26 C25 C24 120.4(4) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 120.6(4) . . ?
C25 C26 Br2 119.4(3) . . ?
C27 C26 Br2 120.0(4) . . ?
C26 C27 C28 119.0(4) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C23 C28 C27 120.3(4) . . ?
C23 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O2 C1 O1 -176.4(5) . . . . ?
C4 O2 C1 C2 3.7(6) . . . . ?
O1 C1 C2 C5 9.3(8) . . . . ?
O2 C1 C2 C5 -170.8(5) . . . . ?
O1 C1 C2 C3 -167.1(4) . . . . ?
O2 C1 C2 C3 12.8(5) . . . . ?
C5 C2 C3 C6 34.8(7) . . . . ?
C1 C2 C3 C6 -149.0(4) . . . . ?
C5 C2 C3 C4 161.6(5) . . . . ?
C1 C2 C3 C4 -22.2(5) . . . . ?
C1 O2 C4 C3 -18.3(6) . . . . ?
C6 C3 C4 O2 151.7(4) . . . . ?
C2 C3 C4 O2 24.0(5) . . . . ?
C2 C3 C6 C7 -166.5(4) . . . . ?
C4 C3 C6 C7 74.8(5) . . . . ?
C8 O3 C7 C6 172.7(3) . . . . ?
C3 C6 C7 O3 -60.0(5) . . . . ?
C9 N1 C8 O4 4.4(7) . . . . ?
C9 N1 C8 O3 -175.5(3) . . . . ?
C7 O3 C8 O4 -0.5(6) . . . . ?
C7 O3 C8 N1 179.4(3) . . . . ?
C8 N1 C9 C10 19.6(6) . . . . ?
C8 N1 C9 C14 -160.8(4) . . . . ?
C14 C9 C10 C11 -0.3(6) . . . . ?
N1 C9 C10 C11 179.3(4) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C10 C11 C12 Br1 179.5(3) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
Br1 C12 C13 C14 -179.2(3) . . . . ?
C12 C13 C14 C9 -1.0(6) . . . . ?
C10 C9 C14 C13 0.6(6) . . . . ?
N1 C9 C14 C13 -179.0(4) . . . . ?
C18 O6 C16 O5 -169.5(4) . . . . ?
C18 O6 C16 C15 11.3(4) . . . . ?
C19 C15 C16 O5 12.4(7) . . . . ?
C17 C15 C16 O5 -170.4(4) . . . . ?
C19 C15 C16 O6 -168.5(4) . . . . ?
C17 C15 C16 O6 8.6(4) . . . . ?
C19 C15 C17 C18 153.2(5) . . . . ?
C16 C15 C17 C18 -23.5(4) . . . . ?
C19 C15 C17 C20 29.2(6) . . . . ?
C16 C15 C17 C20 -147.6(3) . . . . ?
C16 O6 C18 C17 -26.5(4) . . . . ?
C15 C17 C18 O6 29.7(4) . . . . ?
C20 C17 C18 O6 153.8(3) . . . . ?
C15 C17 C20 C21 -167.9(3) . . . . ?
C18 C17 C20 C21 75.5(4) . . . . ?
C22 O7 C21 C20 -175.7(3) . . . . ?
C17 C20 C21 O7 177.2(3) . . . . ?
C23 N2 C22 O8 -4.1(7) . . . . ?
C23 N2 C22 O7 176.3(3) . . . . ?
C21 O7 C22 O8 -0.3(5) . . . . ?
C21 O7 C22 N2 179.4(3) . . . . ?
C22 N2 C23 C28 -19.6(6) . . . . ?
C22 N2 C23 C24 162.8(4) . . . . ?
C28 C23 C24 C25 1.4(6) . . . . ?
N2 C23 C24 C25 179.1(4) . . . . ?
C23 C24 C25 C26 -0.3(6) . . . . ?
C24 C25 C26 C27 -0.7(6) . . . . ?
C24 C25 C26 Br2 177.8(3) . . . . ?
C25 C26 C27 C28 0.5(6) . . . . ?
Br2 C26 C27 C28 -177.9(3) . . . . ?
C24 C23 C28 C27 -1.6(6) . . . . ?
N2 C23 C28 C27 -179.1(4) . . . . ?
C26 C27 C28 C23 0.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.62
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 934199'
