# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

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#
#                 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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 Br2 N2 O2'
_chemical_formula_weight         391.09

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'

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

_cell_length_a                   7.3552(5)
_cell_length_b                   18.8781(8)
_cell_length_c                   21.2531(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2951.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2772
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.094
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544
_exptl_absorpt_coefficient_mu    5.493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  'Xcalibur, Onyx'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.2634
_diffrn_standards_number         0
_diffrn_reflns_number            39506
_diffrn_reflns_av_R_equivalents  0.1230
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.08
_diffrn_reflns_theta_max         24.84
_reflns_number_total             5091
_reflns_number_gt                4786
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX  (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0470P)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   -0.013(8)
_refine_ls_number_reflns         5091
_refine_ls_number_parameters     343
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.002
_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
Br1A Br 0.88658(6) 0.90441(3) 0.93972(2) 0.03268(13) Uani 1 1 d . . .
Br2A Br 0.75282(7) 0.82460(2) 1.07673(3) 0.03651(13) Uani 1 1 d . . .
O1A O 0.5339(4) 0.99631(14) 1.23891(13) 0.0227(7) Uani 1 1 d . . .
N1A N 0.6001(4) 1.05876(18) 1.22916(15) 0.0150(7) Uani 1 1 d . . .
N2A N 0.7279(4) 1.1521(2) 1.18458(17) 0.0202(8) Uani 1 1 d . . .
C1A C 0.5621(5) 1.1176(2) 1.27576(18) 0.0181(8) Uani 1 1 d . . .
C2A C 0.6961(5) 1.1761(2) 1.2515(2) 0.0193(9) Uani 1 1 d . . .
C3A C 0.3591(5) 1.1375(2) 1.2679(2) 0.0268(11) Uani 1 1 d . . .
H3A1 H 0.3375 1.1526 1.2254 0.040 Uiso 1 1 calc R . .
H3A2 H 0.3291 1.1752 1.2963 0.040 Uiso 1 1 calc R . .
H3A3 H 0.2848 1.0970 1.2770 0.040 Uiso 1 1 calc R . .
C4A C 0.5969(6) 1.0916(3) 1.3428(2) 0.0310(11) Uani 1 1 d . . .
H4A1 H 0.5114 1.0549 1.3531 0.047 Uiso 1 1 calc R . .
H4A2 H 0.5829 1.1303 1.3717 0.047 Uiso 1 1 calc R . .
H4A3 H 0.7183 1.0731 1.3458 0.047 Uiso 1 1 calc R . .
C5A C 0.6223(6) 1.2511(2) 1.2513(2) 0.0291(10) Uani 1 1 d . . .
H5A1 H 0.5033 1.2514 1.2327 0.044 Uiso 1 1 calc R . .
H5A2 H 0.7018 1.2810 1.2273 0.044 Uiso 1 1 calc R . .
H5A3 H 0.6151 1.2684 1.2937 0.044 Uiso 1 1 calc R . .
C6A C 0.8847(5) 1.1737(3) 1.2838(2) 0.0296(11) Uani 1 1 d . . .
H6A1 H 0.9282 1.1258 1.2846 0.044 Uiso 1 1 calc R . .
H6A2 H 0.8742 1.1911 1.3261 0.044 Uiso 1 1 calc R . .
H6A3 H 0.9686 1.2028 1.2608 0.044 Uiso 1 1 calc R . .
C7A C 0.6847(5) 1.0821(2) 1.17575(19) 0.0169(9) Uani 1 1 d . . .
C8A C 0.7301(5) 1.0394(2) 1.12012(19) 0.0163(9) Uani 1 1 d . . .
C9A C 0.7882(5) 1.0718(2) 1.06310(19) 0.0209(9) Uani 1 1 d . . .
H9A H 0.7955 1.1209 1.0606 0.025 Uiso 1 1 calc R . .
C10A C 0.8345(5) 1.0305(2) 1.01079(19) 0.0230(9) Uani 1 1 d . . .
H10A H 0.8726 1.0524 0.9739 0.028 Uiso 1 1 calc R . .
C11A C 0.8242(5) 0.9572(2) 1.01332(19) 0.0228(9) Uani 1 1 d . . .
C12A C 0.7691(5) 0.9243(2) 1.0701(2) 0.0216(9) Uani 1 1 d . . .
C13A C 0.7201(5) 0.9646(2) 1.12233(19) 0.0203(9) Uani 1 1 d . . .
H13A H 0.6807 0.9423 1.1588 0.024 Uiso 1 1 calc R . .
Br1B Br 0.80813(6) 0.69433(2) 0.86338(3) 0.03422(13) Uani 1 1 d . . .
Br2B Br 0.84752(7) 0.63071(3) 0.71308(2) 0.04662(16) Uani 1 1 d . . .
O1B O 0.8500(5) 0.32742(18) 0.89593(17) 0.0377(8) Uani 1 1 d . . .
N1B N 0.7704(4) 0.36185(19) 0.94107(17) 0.0208(8) Uani 1 1 d . . .
N2B N 0.6330(4) 0.44635(18) 0.99483(15) 0.0175(7) Uani 1 1 d . . .
C1B C 0.7557(5) 0.3297(2) 1.0064(2) 0.0209(9) Uani 1 1 d . . .
C2B C 0.6310(5) 0.3854(2) 1.0408(2) 0.0204(9) Uani 1 1 d . . .
C3B C 0.9516(6) 0.3255(2) 1.0321(2) 0.0308(11) Uani 1 1 d . . .
H3B1 H 1.0000 0.3725 1.0363 0.046 Uiso 1 1 calc R . .
H3B2 H 1.0258 0.2988 1.0035 0.046 Uiso 1 1 calc R . .
H3B3 H 0.9508 0.3027 1.0725 0.046 Uiso 1 1 calc R . .
C4B C 0.6759(6) 0.2556(2) 1.0005(2) 0.0283(10) Uani 1 1 d . . .
H4B1 H 0.5548 0.2586 0.9838 0.043 Uiso 1 1 calc R . .
H4B2 H 0.6726 0.2335 1.0412 0.043 Uiso 1 1 calc R . .
H4B3 H 0.7501 0.2278 0.9726 0.043 Uiso 1 1 calc R . .
C5B C 0.7040(7) 0.4131(3) 1.1046(2) 0.0309(11) Uani 1 1 d . . .
H5B1 H 0.8291 0.4266 1.1000 0.046 Uiso 1 1 calc R . .
H5B2 H 0.6944 0.3763 1.1357 0.046 Uiso 1 1 calc R . .
H5B3 H 0.6338 0.4533 1.1177 0.046 Uiso 1 1 calc R . .
C6B C 0.4298(5) 0.3634(2) 1.0479(2) 0.0244(10) Uani 1 1 d . . .
H6B1 H 0.3853 0.3459 1.0084 0.037 Uiso 1 1 calc R . .
H6B2 H 0.3591 0.4036 1.0607 0.037 Uiso 1 1 calc R . .
H6B3 H 0.4201 0.3268 1.0792 0.037 Uiso 1 1 calc R . .
C7B C 0.7086(5) 0.4296(2) 0.9385(2) 0.0164(8) Uani 1 1 d . . .
C8B C 0.7317(5) 0.4779(2) 0.88378(19) 0.0177(9) Uani 1 1 d . . .
C9B C 0.7489(6) 0.4515(2) 0.8226(2) 0.0251(9) Uani 1 1 d . . .
H9B H 0.7403 0.4030 0.8152 0.030 Uiso 1 1 calc R . .
C10B C 0.7793(6) 0.4985(3) 0.7723(2) 0.0311(12) Uani 1 1 d . . .
H10B H 0.7887 0.4809 0.7315 0.037 Uiso 1 1 calc R . .
C11B C 0.7953(6) 0.5703(3) 0.7829(2) 0.0270(10) Uani 1 1 d . . .
C12B C 0.7763(5) 0.5964(2) 0.8448(2) 0.0244(10) Uani 1 1 d . . .
C13B C 0.7428(5) 0.5509(2) 0.89455(19) 0.0190(9) Uani 1 1 d . . .
H13B H 0.7278 0.5688 0.9350 0.023 Uiso 1 1 calc R . .
O2B O 0.5558(4) 0.50574(14) 1.00911(13) 0.0261(7) Uani 1 1 d . . .
O2A O 0.8083(5) 1.19295(17) 1.14462(16) 0.0355(8) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1A C11A 1.910(4) . ?
Br2A C12A 1.892(4) . ?
O1A N1A 1.292(4) . ?
N1A C7A 1.368(5) . ?
N1A C1A 1.514(5) . ?
N2A O2A 1.291(5) . ?
N2A C7A 1.371(6) . ?
N2A C2A 1.512(6) . ?
C1A C4A 1.529(6) . ?
C1A C3A 1.549(5) . ?
C1A C2A 1.567(6) . ?
C2A C5A 1.517(6) . ?
C2A C6A 1.549(6) . ?
C3A H3A1 0.9600 . ?
C3A H3A2 0.9600 . ?
C3A H3A3 0.9600 . ?
C4A H4A1 0.9600 . ?
C4A H4A2 0.9600 . ?
C4A H4A3 0.9600 . ?
C5A H5A1 0.9600 . ?
C5A H5A2 0.9600 . ?
C5A H5A3 0.9600 . ?
C6A H6A1 0.9600 . ?
C6A H6A2 0.9600 . ?
C6A H6A3 0.9600 . ?
C7A C8A 1.470(6) . ?
C8A C13A 1.414(6) . ?
C8A C9A 1.423(6) . ?
C9A C10A 1.400(6) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.386(7) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.415(6) . ?
C12A C13A 1.394(6) . ?
C13A H13A 0.9300 . ?
Br1B C12B 1.905(5) . ?
Br2B C11B 1.910(4) . ?
O1B N1B 1.298(5) . ?
N1B C7B 1.358(5) . ?
N1B C1B 1.520(6) . ?
N2B O2B 1.293(4) . ?
N2B C7B 1.357(5) . ?
N2B C2B 1.510(5) . ?
C1B C4B 1.522(6) . ?
C1B C3B 1.543(6) . ?
C1B C2B 1.576(6) . ?
C2B C6B 1.544(6) . ?
C2B C5B 1.549(6) . ?
C3B H3B1 0.9600 . ?
C3B H3B2 0.9600 . ?
C3B H3B3 0.9600 . ?
C4B H4B1 0.9600 . ?
C4B H4B2 0.9600 . ?
C4B H4B3 0.9600 . ?
C5B H5B1 0.9600 . ?
C5B H5B2 0.9600 . ?
C5B H5B3 0.9600 . ?
C6B H6B1 0.9600 . ?
C6B H6B2 0.9600 . ?
C6B H6B3 0.9600 . ?
C7B C8B 1.487(6) . ?
C8B C9B 1.398(6) . ?
C8B C13B 1.401(6) . ?
C9B C10B 1.408(6) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.379(7) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.412(6) . ?
C12B C13B 1.384(6) . ?
C13B H13B 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
O1A N1A C7A 126.8(3) . . ?
O1A N1A C1A 119.7(3) . . ?
C7A N1A C1A 113.0(3) . . ?
O2A N2A C7A 126.3(4) . . ?
O2A N2A C2A 120.7(3) . . ?
C7A N2A C2A 112.4(3) . . ?
N1A C1A C4A 110.1(3) . . ?
N1A C1A C3A 106.5(3) . . ?
C4A C1A C3A 109.9(4) . . ?
N1A C1A C2A 100.7(3) . . ?
C4A C1A C2A 115.3(3) . . ?
C3A C1A C2A 113.6(4) . . ?
N2A C2A C5A 109.4(4) . . ?
N2A C2A C6A 105.7(3) . . ?
C5A C2A C6A 110.4(4) . . ?
N2A C2A C1A 101.3(3) . . ?
C5A C2A C1A 115.7(3) . . ?
C6A C2A C1A 113.4(4) . . ?
C1A C3A H3A1 109.5 . . ?
C1A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C1A C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
C1A C4A H4A1 109.5 . . ?
C1A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C1A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C2A C5A H5A1 109.5 . . ?
C2A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
C2A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
C2A C6A H6A1 109.5 . . ?
C2A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
C2A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?
N1A C7A N2A 107.6(4) . . ?
N1A C7A C8A 126.4(4) . . ?
N2A C7A C8A 125.9(4) . . ?
C13A C8A C9A 118.2(4) . . ?
C13A C8A C7A 120.6(4) . . ?
C9A C8A C7A 121.2(4) . . ?
C10A C9A C8A 120.7(4) . . ?
C10A C9A H9A 119.7 . . ?
C8A C9A H9A 119.7 . . ?
C11A C10A C9A 120.8(4) . . ?
C11A C10A H10A 119.6 . . ?
C9A C10A H10A 119.6 . . ?
C10A C11A C12A 119.1(4) . . ?
C10A C11A Br1A 118.4(3) . . ?
C12A C11A Br1A 122.5(3) . . ?
C13A C12A C11A 120.9(4) . . ?
C13A C12A Br2A 117.9(3) . . ?
C11A C12A Br2A 121.2(3) . . ?
C12A C13A C8A 120.3(4) . . ?
C12A C13A H13A 119.8 . . ?
C8A C13A H13A 119.8 . . ?
O1B N1B C7B 126.3(4) . . ?
O1B N1B C1B 120.5(3) . . ?
C7B N1B C1B 112.9(3) . . ?
O2B N2B C7B 126.1(3) . . ?
O2B N2B C2B 120.3(3) . . ?
C7B N2B C2B 113.4(3) . . ?
N1B C1B C4B 108.6(4) . . ?
N1B C1B C3B 106.1(3) . . ?
C4B C1B C3B 110.1(4) . . ?
N1B C1B C2B 101.4(3) . . ?
C4B C1B C2B 115.3(3) . . ?
C3B C1B C2B 114.4(4) . . ?
N2B C2B C6B 106.2(3) . . ?
N2B C2B C5B 107.8(3) . . ?
C6B C2B C5B 109.7(4) . . ?
N2B C2B C1B 101.7(3) . . ?
C6B C2B C1B 115.0(4) . . ?
C5B C2B C1B 115.4(4) . . ?
C1B C3B H3B1 109.5 . . ?
C1B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C1B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
C1B C4B H4B1 109.5 . . ?
C1B C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
C1B C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
C2B C5B H5B1 109.5 . . ?
C2B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
C2B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
C2B C6B H6B1 109.5 . . ?
C2B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 109.5 . . ?
C2B C6B H6B3 109.5 . . ?
H6B1 C6B H6B3 109.5 . . ?
H6B2 C6B H6B3 109.5 . . ?
N2B C7B N1B 108.7(4) . . ?
N2B C7B C8B 126.4(4) . . ?
N1B C7B C8B 124.8(4) . . ?
C9B C8B C13B 119.9(4) . . ?
C9B C8B C7B 121.3(4) . . ?
C13B C8B C7B 118.8(4) . . ?
C8B C9B C10B 119.8(4) . . ?
C8B C9B H9B 120.1 . . ?
C10B C9B H9B 120.1 . . ?
C11B C10B C9B 120.6(4) . . ?
C11B C10B H10B 119.7 . . ?
C9B C10B H10B 119.7 . . ?
C10B C11B C12B 119.1(4) . . ?
C10B C11B Br2B 118.5(3) . . ?
C12B C11B Br2B 122.3(4) . . ?
C13B C12B C11B 120.9(4) . . ?
C13B C12B Br1B 117.7(3) . . ?
C11B C12B Br1B 121.4(3) . . ?
C12B C13B C8B 119.7(4) . . ?
C12B C13B H13B 120.1 . . ?
C8B C13B H13B 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.84
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.084
_database_code_depnum_ccdc_archive 'CCDC 996671'
#######################################################################
#
#                 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_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 Br2 N2 O'
_chemical_formula_weight         375.09

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'

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

_cell_length_a                   7.3060(4)
_cell_length_b                   18.7395(9)
_cell_length_c                   20.9306(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2865.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2438
_cell_measurement_theta_min      3
_cell_measurement_theta_max      28

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1480
_exptl_absorpt_coefficient_mu    5.648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5966
_exptl_absorpt_correction_T_max  0.6363
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  'Xcalibur, Onyx'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.2634
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39962
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.09
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5086
_reflns_number_gt                4278
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX  (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0427P)²+1.9124P] 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   -0.001(10)
_refine_ls_number_reflns         5086
_refine_ls_number_parameters     334
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1A Br 0.12556(8) 0.10062(3) 0.06122(3) 0.05151(18) Uani 1 1 d . . .
Br2A Br 0.26533(10) 0.17959(3) -0.07553(4) 0.05616(19) Uani 1 1 d . . .
O1A O 0.4554(6) 0.0026(2) -0.24204(19) 0.0501(10) Uani 1 1 d . . .
N1A N 0.3873(5) -0.05704(19) -0.23056(17) 0.0215(8) Uani 1 1 d . . .
N2A N 0.2514(6) -0.1475(2) -0.1794(2) 0.0318(10) Uani 1 1 d . . .
C1A C 0.4191(7) -0.1177(3) -0.2741(2) 0.0305(12) Uani 1 1 d . . .
C2A C 0.2841(7) -0.1735(3) -0.2449(3) 0.0304(12) Uani 1 1 d . . .
C3A C 0.6191(6) -0.1389(3) -0.2674(3) 0.0380(13) Uani 1 1 d . . .
H3A1 H 0.6438 -0.1527 -0.2231 0.057 Uiso 1 1 calc R . .
H3A2 H 0.6972 -0.0985 -0.2792 0.057 Uiso 1 1 calc R . .
H3A3 H 0.6451 -0.1794 -0.2957 0.057 Uiso 1 1 calc R . .
C4A C 0.3817(9) -0.0950(4) -0.3427(3) 0.0539(17) Uani 1 1 d . . .
H4A1 H 0.2535 -0.0803 -0.3468 0.081 Uiso 1 1 calc R . .
H4A2 H 0.4058 -0.1352 -0.3715 0.081 Uiso 1 1 calc R . .
H4A3 H 0.4616 -0.0549 -0.3540 0.081 Uiso 1 1 calc R . .
C5A C 0.3546(9) -0.2489(3) -0.2421(3) 0.0531(17) Uani 1 1 d . . .
H5A1 H 0.4745 -0.2494 -0.2212 0.080 Uiso 1 1 calc R . .
H5A2 H 0.3664 -0.2677 -0.2856 0.080 Uiso 1 1 calc R . .
H5A3 H 0.2688 -0.2785 -0.2178 0.080 Uiso 1 1 calc R . .
C6A C 0.0965(7) -0.1734(3) -0.2778(3) 0.0450(15) Uani 1 1 d . . .
H6A1 H 0.0499 -0.1244 -0.2801 0.067 Uiso 1 1 calc R . .
H6A2 H 0.0110 -0.2029 -0.2533 0.067 Uiso 1 1 calc R . .
H6A3 H 0.1088 -0.1926 -0.3211 0.067 Uiso 1 1 calc R . .
C7A C 0.3019(6) -0.0799(2) -0.1758(2) 0.0217(11) Uani 1 1 d . . .
C8A C 0.2679(6) -0.0351(2) -0.1192(2) 0.0228(10) Uani 1 1 d . . .
C9A C 0.2120(6) -0.0667(3) -0.0630(2) 0.0306(12) Uani 1 1 d . . .
H9A H 0.2007 -0.1171 -0.0608 0.037 Uiso 1 1 calc R . .
C10A C 0.1724(7) -0.0258(3) -0.0101(2) 0.0363(13) Uani 1 1 d . . .
H10A H 0.1357 -0.0481 0.0286 0.044 Uiso 1 1 calc R . .
C11A C 0.1862(7) 0.0474(3) -0.0136(2) 0.0314(12) Uani 1 1 d . . .
C12A C 0.2405(7) 0.0799(2) -0.0693(3) 0.0321(12) Uani 1 1 d . . .
C13A C 0.2828(6) 0.0393(3) -0.1223(2) 0.0243(11) Uani 1 1 d . . .
H13A H 0.3218 0.0617 -0.1607 0.029 Uiso 1 1 calc R . .
Br1B Br 0.21546(9) 0.30582(3) 0.13630(3) 0.05524(19) Uani 1 1 d . . .
Br2B Br 0.17118(10) 0.37158(4) 0.28582(3) 0.0694(2) Uani 1 1 d . . .
O1B O 0.1726(10) 0.6745(4) 0.0985(4) 0.0388(18) Uani 0.50 1 d P . .
N1B N 0.2311(6) 0.6378(2) 0.0549(2) 0.0367(11) Uani 1 1 d . . .
N2B N 0.3635(5) 0.5487(2) 0.00126(19) 0.0269(9) Uani 1 1 d . . .
C1B C 0.2386(7) 0.6644(3) -0.0125(3) 0.0354(13) Uani 1 1 d . . .
C2B C 0.3671(7) 0.6097(3) -0.0440(2) 0.0327(12) Uani 1 1 d . . .
C3B C 0.0396(8) 0.6606(4) -0.0364(3) 0.065(2) Uani 1 1 d . . .
H3B1 H -0.0034 0.6112 -0.0346 0.098 Uiso 1 1 calc R . .
H3B2 H 0.0337 0.6779 -0.0806 0.098 Uiso 1 1 calc R . .
H3B3 H -0.0383 0.6906 -0.0093 0.098 Uiso 1 1 calc R . .
C4B C 0.3033(9) 0.7413(3) -0.0135(4) 0.065(2) Uani 1 1 d . . .
H4B1 H 0.2123 0.7716 0.0076 0.097 Uiso 1 1 calc R . .
H4B2 H 0.3190 0.7569 -0.0578 0.097 Uiso 1 1 calc R . .
H4B3 H 0.4204 0.7450 0.0091 0.097 Uiso 1 1 calc R . .
C5B C 0.3080(9) 0.5813(3) -0.1097(3) 0.0511(17) Uani 1 1 d . . .
H5B1 H 0.1807 0.5649 -0.1076 0.077 Uiso 1 1 calc R . .
H5B2 H 0.3871 0.5414 -0.1220 0.077 Uiso 1 1 calc R . .
H5B3 H 0.3184 0.6195 -0.1415 0.077 Uiso 1 1 calc R . .
C6B C 0.5656(7) 0.6344(3) -0.0478(3) 0.0390(13) Uani 1 1 d . . .
H6B1 H 0.6048 0.6520 -0.0058 0.058 Uiso 1 1 calc R . .
H6B2 H 0.5761 0.6729 -0.0793 0.058 Uiso 1 1 calc R . .
H6B3 H 0.6435 0.5944 -0.0606 0.058 Uiso 1 1 calc R . .
C7B C 0.2911(6) 0.5695(2) 0.0567(2) 0.0247(10) Uani 1 1 d . . .
C8B C 0.2709(6) 0.5230(3) 0.1125(2) 0.0259(11) Uani 1 1 d . . .
C9B C 0.2502(8) 0.5503(3) 0.1738(3) 0.0387(12) Uani 1 1 d . . .
H9B H 0.2545 0.6003 0.1809 0.046 Uiso 1 1 calc R . .
C10B C 0.2233(8) 0.5043(4) 0.2245(3) 0.0498(16) Uani 1 1 d . . .
H10B H 0.2098 0.5231 0.2664 0.060 Uiso 1 1 calc R . .
C11B C 0.2159(7) 0.4313(3) 0.2152(3) 0.0398(14) Uani 1 1 d . . .
C12B C 0.2362(6) 0.4045(3) 0.1539(2) 0.0299(12) Uani 1 1 d . . .
C13B C 0.2660(6) 0.4494(3) 0.1030(2) 0.0276(11) Uani 1 1 d . . .
H13B H 0.2831 0.4304 0.0613 0.033 Uiso 1 1 calc R . .
O2B O 0.4407(13) 0.4970(4) -0.0120(4) 0.058(2) Uani 0.50 1 d P . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1A C11A 1.908(5) . ?
Br2A C12A 1.881(5) . ?
O1A N1A 1.247(5) . ?
N1A C7A 1.373(6) . ?
N1A C1A 1.475(6) . ?
N2A C7A 1.321(6) . ?
N2A C2A 1.474(7) . ?
C1A C3A 1.521(7) . ?
C1A C4A 1.521(8) . ?
C1A C2A 1.563(7) . ?
C2A C5A 1.505(7) . ?
C2A C6A 1.534(7) . ?
C3A H3A1 0.9800 . ?
C3A H3A2 0.9800 . ?
C3A H3A3 0.9800 . ?
C4A H4A1 0.9800 . ?
C4A H4A2 0.9800 . ?
C4A H4A3 0.9800 . ?
C5A H5A1 0.9800 . ?
C5A H5A2 0.9800 . ?
C5A H5A3 0.9800 . ?
C6A H6A1 0.9800 . ?
C6A H6A2 0.9800 . ?
C6A H6A3 0.9800 . ?
C7A C8A 1.474(7) . ?
C8A C9A 1.378(7) . ?
C8A C13A 1.399(7) . ?
C9A C10A 1.377(7) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.378(8) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.375(8) . ?
C12A C13A 1.381(7) . ?
C13A H13A 0.9500 . ?
Br1B C12B 1.891(5) . ?
Br2B C11B 1.881(5) . ?
O1B N1B 1.220(8) . ?
N1B C7B 1.354(6) . ?
N1B C1B 1.496(7) . ?
N2B O2B 1.155(8) . ?
N2B C7B 1.332(6) . ?
N2B C2B 1.484(6) . ?
C1B C4B 1.517(8) . ?
C1B C2B 1.539(8) . ?
C1B C3B 1.540(8) . ?
C2B C6B 1.525(7) . ?
C2B C5B 1.537(8) . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C3B H3B3 0.9800 . ?
C4B H4B1 0.9800 . ?
C4B H4B2 0.9800 . ?
C4B H4B3 0.9800 . ?
C5B H5B1 0.9800 . ?
C5B H5B2 0.9800 . ?
C5B H5B3 0.9800 . ?
C6B H6B1 0.9800 . ?
C6B H6B2 0.9800 . ?
C6B H6B3 0.9800 . ?
C7B C8B 1.465(7) . ?
C8B C9B 1.390(8) . ?
C8B C13B 1.394(7) . ?
C9B C10B 1.381(8) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.383(9) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.387(8) . ?
C12B C13B 1.376(7) . ?
C13B H13B 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
O1A N1A C7A 128.4(4) . . ?
O1A N1A C1A 120.6(4) . . ?
C7A N1A C1A 110.3(4) . . ?
C7A N2A C2A 108.9(4) . . ?
N1A C1A C3A 107.2(4) . . ?
N1A C1A C4A 109.9(4) . . ?
C3A C1A C4A 109.4(5) . . ?
N1A C1A C2A 100.0(4) . . ?
C3A C1A C2A 113.2(4) . . ?
C4A C1A C2A 116.3(5) . . ?
N2A C2A C5A 109.3(5) . . ?
N2A C2A C6A 105.9(4) . . ?
C5A C2A C6A 108.9(5) . . ?
N2A C2A C1A 104.2(4) . . ?
C5A C2A C1A 115.3(4) . . ?
C6A C2A C1A 112.7(4) . . ?
C1A C3A H3A1 109.5 . . ?
C1A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C1A C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
C1A C4A H4A1 109.5 . . ?
C1A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C1A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C2A C5A H5A1 109.5 . . ?
C2A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
C2A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
C2A C6A H6A1 109.5 . . ?
C2A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
C2A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?
N2A C7A N1A 112.3(4) . . ?
N2A C7A C8A 123.0(4) . . ?
N1A C7A C8A 124.7(4) . . ?
C9A C8A C13A 119.4(5) . . ?
C9A C8A C7A 119.4(4) . . ?
C13A C8A C7A 121.1(5) . . ?
C10A C9A C8A 120.6(5) . . ?
C10A C9A H9A 119.7 . . ?
C8A C9A H9A 119.7 . . ?
C11A C10A C9A 119.7(5) . . ?
C11A C10A H10A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
C12A C11A C10A 120.5(5) . . ?
C12A C11A Br1A 122.1(4) . . ?
C10A C11A Br1A 117.4(4) . . ?
C11A C12A C13A 120.1(4) . . ?
C11A C12A Br2A 121.8(4) . . ?
C13A C12A Br2A 118.1(4) . . ?
C12A C13A C8A 119.6(5) . . ?
C12A C13A H13A 120.2 . . ?
C8A C13A H13A 120.2 . . ?
O1B N1B C7B 128.8(5) . . ?
O1B N1B C1B 122.0(5) . . ?
C7B N1B C1B 109.1(4) . . ?
O2B N2B C7B 130.4(6) . . ?
O2B N2B C2B 118.9(5) . . ?
C7B N2B C2B 109.7(4) . . ?
N1B C1B C4B 109.9(5) . . ?
N1B C1B C2B 101.8(4) . . ?
C4B C1B C2B 115.9(5) . . ?
N1B C1B C3B 104.9(4) . . ?
C4B C1B C3B 109.4(5) . . ?
C2B C1B C3B 114.0(5) . . ?
N2B C2B C6B 106.5(4) . . ?
N2B C2B C5B 107.5(4) . . ?
C6B C2B C5B 109.0(5) . . ?
N2B C2B C1B 103.2(4) . . ?
C6B C2B C1B 113.5(4) . . ?
C5B C2B C1B 116.3(5) . . ?
C1B C3B H3B1 109.5 . . ?
C1B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C1B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
C1B C4B H4B1 109.5 . . ?
C1B C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
C1B C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
C2B C5B H5B1 109.5 . . ?
C2B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
C2B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
C2B C6B H6B1 109.5 . . ?
C2B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 109.5 . . ?
C2B C6B H6B3 109.5 . . ?
H6B1 C6B H6B3 109.5 . . ?
H6B2 C6B H6B3 109.5 . . ?
N2B C7B N1B 112.4(4) . . ?
N2B C7B C8B 124.1(4) . . ?
N1B C7B C8B 123.4(5) . . ?
C9B C8B C13B 119.6(5) . . ?
C9B C8B C7B 122.0(4) . . ?
C13B C8B C7B 118.4(5) . . ?
C10B C9B C8B 119.7(5) . . ?
C10B C9B H9B 120.1 . . ?
C8B C9B H9B 120.1 . . ?
C11B C10B C9B 121.0(5) . . ?
C11B C10B H10B 119.5 . . ?
C9B C10B H10B 119.5 . . ?
C10B C11B C12B 119.0(5) . . ?
C10B C11B Br2B 119.0(5) . . ?
C12B C11B Br2B 122.0(4) . . ?
C13B C12B C11B 120.8(5) . . ?
C13B C12B Br1B 117.4(4) . . ?
C11B C12B Br1B 121.7(4) . . ?
C12B C13B C8B 119.9(5) . . ?
C12B C13B H13B 120.0 . . ?
C8B C13B H13B 120.0 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.079
_database_code_depnum_ccdc_archive 'CCDC 996672'
#######################################################################
#
#                 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_4'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Br N3 O2'
_chemical_formula_weight         337.20

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   'P 21/c'

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

_cell_length_a                   7.4256(10)
_cell_length_b                   16.678(3)
_cell_length_c                   11.512(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.259(3)
_cell_angle_gamma                90.00
_cell_volume                     1398.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2887
_cell_measurement_theta_min      3.2910
_cell_measurement_theta_max      26.2960

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.639
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.058
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684
_exptl_absorpt_coefficient_mu    2.945
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  'Xcalibur, Onyx'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.2634
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12503
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3159
_reflns_number_gt                2748
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX  (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0383P)²+1.5220P] 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_number_reflns         3159
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2899(3) 0.01724(11) 0.07725(18) 0.0298(4) Uani 1 1 d . . .
O2 O 0.1943(3) -0.17469(11) 0.35092(16) 0.0342(5) Uani 1 1 d . . .
N1 N 0.2562(3) -0.04802(12) 0.12629(18) 0.0197(4) Uani 1 1 d . . .
N2 N 0.2059(3) -0.13845(12) 0.25496(18) 0.0210(4) Uani 1 1 d . . .
N3 N 0.3348(4) 0.23183(15) 0.6657(2) 0.0333(6) Uani 1 1 d . . .
C1 C 0.2411(3) -0.12554(14) 0.0576(2) 0.0197(5) Uani 1 1 d . . .
C2 C 0.1436(4) -0.17857(15) 0.1368(2) 0.0209(5) Uani 1 1 d . . .
C3 C 0.4364(4) -0.15121(17) 0.0530(3) 0.0292(6) Uani 1 1 d . . .
H3A H 0.5043 -0.1592 0.1320 0.044 Uiso 1 1 calc R . .
H3B H 0.4946 -0.1103 0.0147 0.044 Uiso 1 1 calc R . .
H3C H 0.4333 -0.2004 0.0092 0.044 Uiso 1 1 calc R . .
C4 C 0.1307(4) -0.11246(18) -0.0670(2) 0.0310(6) Uani 1 1 d . . .
H4A H 0.0081 -0.0963 -0.0626 0.047 Uiso 1 1 calc R . .
H4B H 0.1265 -0.1615 -0.1112 0.047 Uiso 1 1 calc R . .
H4C H 0.1879 -0.0714 -0.1056 0.047 Uiso 1 1 calc R . .
C5 C -0.0660(4) -0.17013(18) 0.1094(2) 0.0304(6) Uani 1 1 d . . .
H5A H -0.0983 -0.1143 0.1058 0.046 Uiso 1 1 calc R . .
H5B H -0.1163 -0.1958 0.1706 0.046 Uiso 1 1 calc R . .
H5C H -0.1145 -0.1950 0.0346 0.046 Uiso 1 1 calc R . .
C6 C 0.2005(5) -0.26622(16) 0.1432(3) 0.0317(6) Uani 1 1 d . . .
H6A H 0.3321 -0.2699 0.1604 0.048 Uiso 1 1 calc R . .
H6B H 0.1536 -0.2917 0.0686 0.048 Uiso 1 1 calc R . .
H6C H 0.1518 -0.2925 0.2045 0.048 Uiso 1 1 calc R . .
C7 C 0.2482(3) -0.06047(14) 0.2416(2) 0.0184(5) Uani 1 1 d . . .
C8 C 0.2720(3) 0.00118(14) 0.3343(2) 0.0181(5) Uani 1 1 d . . .
C9 C 0.3103(3) 0.08086(15) 0.3086(2) 0.0211(5) Uani 1 1 d . . .
H9 H 0.3244 0.0947 0.2326 0.025 Uiso 1 1 calc R . .
C10 C 0.3268(4) 0.13862(15) 0.3954(2) 0.0232(5) Uani 1 1 d . . .
H10 H 0.3530 0.1912 0.3775 0.028 Uiso 1 1 calc R . .
C11 C 0.3050(3) 0.11945(15) 0.5100(2) 0.0205(5) Uani 1 1 d . . .
C12 C 0.2676(3) 0.04017(15) 0.5353(2) 0.0186(5) Uani 1 1 d . . .
C13 C 0.2513(3) -0.01886(14) 0.4493(2) 0.0200(5) Uani 1 1 d . . .
H13 H 0.2268 -0.0715 0.4677 0.024 Uiso 1 1 calc R . .
C14 C 0.3223(3) 0.18253(16) 0.6002(2) 0.0228(5) Uani 1 1 d . . .
Br1 Br 0.24038(4) 0.011591(16) 0.68953(2) 0.02645(11) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.273(3) . ?
O2 N2 1.277(3) . ?
N1 C7 1.356(3) . ?
N1 C1 1.508(3) . ?
N2 C7 1.354(3) . ?
N2 C2 1.506(3) . ?
N3 C14 1.107(3) . ?
C1 C4 1.522(3) . ?
C1 C3 1.523(4) . ?
C1 C2 1.548(3) . ?
C2 C6 1.520(3) . ?
C2 C5 1.533(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.468(3) . ?
C8 C9 1.403(3) . ?
C8 C13 1.402(4) . ?
C9 C10 1.376(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.397(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(3) . ?
C11 C14 1.467(4) . ?
C12 C13 1.385(4) . ?
C12 Br1 1.887(2) . ?
C13 H13 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
O1 N1 C7 127.9(2) . . ?
O1 N1 C1 120.1(2) . . ?
C7 N1 C1 111.65(19) . . ?
O2 N2 C7 127.6(2) . . ?
O2 N2 C2 120.7(2) . . ?
C7 N2 C2 111.17(19) . . ?
N1 C1 C4 110.0(2) . . ?
N1 C1 C3 106.6(2) . . ?
C4 C1 C3 110.4(2) . . ?
N1 C1 C2 100.16(18) . . ?
C4 C1 C2 114.1(2) . . ?
C3 C1 C2 114.7(2) . . ?
N2 C2 C6 110.5(2) . . ?
N2 C2 C5 105.4(2) . . ?
C6 C2 C5 111.1(2) . . ?
N2 C2 C1 100.47(18) . . ?
C6 C2 C1 114.9(2) . . ?
C5 C2 C1 113.5(2) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 N1 108.3(2) . . ?
N2 C7 C8 126.0(2) . . ?
N1 C7 C8 125.6(2) . . ?
C9 C8 C13 119.3(2) . . ?
C9 C8 C7 120.7(2) . . ?
C13 C8 C7 120.0(2) . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 C14 121.7(2) . . ?
C10 C11 C14 119.6(2) . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 Br1 118.87(19) . . ?
C11 C12 Br1 119.94(19) . . ?
C12 C13 C8 119.7(2) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
N3 C14 C11 177.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.096
_database_code_depnum_ccdc_archive 'CCDC 996673'
#######################################################################
#
#                 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_8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H27 N2 O3'
_chemical_formula_weight         331.43

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   6.177(5)
_cell_length_b                   13.704(5)
_cell_length_c                   21.888(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 94.245(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1847.7(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2354
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.089
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Onyx'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.2634
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10869
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         29.48
_reflns_number_total             4391
_reflns_number_gt                3178
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX  (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0971P)²+0.5963P] 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_number_reflns         4391
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1876
_refine_ls_wR_factor_gt          0.1676
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1791(2) 0.10000(11) 0.23204(6) 0.0428(4) Uani 1 1 d . . .
N2 N -0.0028(3) 0.18120(12) 0.30044(7) 0.0512(4) Uani 1 1 d . . .
O1 O 0.3030(3) 0.03601(12) 0.21158(7) 0.0696(5) Uani 1 1 d . . .
O2 O 0.4459(3) -0.24692(10) 0.45562(6) 0.0633(4) Uani 1 1 d . . .
O3 O 0.2992(4) -0.15879(12) 0.53029(7) 0.0958(7) Uani 1 1 d . . .
C1 C 0.0255(3) 0.16048(13) 0.19200(8) 0.0451(4) Uani 1 1 d . . .
C2 C -0.0498(3) 0.23263(14) 0.24083(8) 0.0473(4) Uani 1 1 d . . .
C3 C -0.1522(4) 0.09144(18) 0.16626(11) 0.0702(6) Uani 1 1 d . . .
H3A H -0.2259 0.0639 0.1993 0.105 Uiso 1 1 calc R . .
H3B H -0.0885 0.0400 0.1438 0.105 Uiso 1 1 calc R . .
H3C H -0.2541 0.1269 0.1395 0.105 Uiso 1 1 calc R . .
C4 C 0.1421(4) 0.20367(19) 0.13962(10) 0.0664(6) Uani 1 1 d . . .
H4A H 0.2539 0.2472 0.1557 0.100 Uiso 1 1 calc R . .
H4B H 0.0402 0.2389 0.1127 0.100 Uiso 1 1 calc R . .
H4C H 0.2059 0.1521 0.1173 0.100 Uiso 1 1 calc R . .
C5 C 0.0830(4) 0.32683(15) 0.24511(12) 0.0698(7) Uani 1 1 d . . .
H5A H 0.2349 0.3112 0.2496 0.105 Uiso 1 1 calc R . .
H5B H 0.0448 0.3639 0.2799 0.105 Uiso 1 1 calc R . .
H5C H 0.0529 0.3645 0.2085 0.105 Uiso 1 1 calc R . .
C6 C -0.2901(4) 0.2582(2) 0.23372(12) 0.0709(7) Uani 1 1 d . . .
H6A H -0.3744 0.1993 0.2311 0.106 Uiso 1 1 calc R . .
H6B H -0.3197 0.2959 0.1971 0.106 Uiso 1 1 calc R . .
H6C H -0.3277 0.2956 0.2685 0.106 Uiso 1 1 calc R . .
C7 C 0.1299(3) 0.11125(12) 0.29294(7) 0.0394(4) Uani 1 1 d . . .
C8 C 0.2169(3) 0.04479(12) 0.34187(7) 0.0395(4) Uani 1 1 d . . .
C9 C 0.4231(3) 0.00387(13) 0.34293(8) 0.0464(4) Uani 1 1 d . . .
H9 H 0.5137 0.0185 0.3121 0.056 Uiso 1 1 calc R . .
C10 C 0.4934(3) -0.05877(13) 0.38995(9) 0.0490(4) Uani 1 1 d . . .
H10 H 0.6329 -0.0845 0.3911 0.059 Uiso 1 1 calc R . .
C11 C 0.3583(3) -0.08355(12) 0.43532(8) 0.0446(4) Uani 1 1 d . . .
C12 C 0.1539(3) -0.04251(14) 0.43443(8) 0.0505(5) Uani 1 1 d . . .
H12 H 0.0624 -0.0586 0.4648 0.061 Uiso 1 1 calc R . .
C13 C 0.0842(3) 0.02250(14) 0.38854(8) 0.0484(4) Uani 1 1 d . . .
H13 H -0.0520 0.0513 0.3890 0.058 Uiso 1 1 calc R . .
C14 C 0.4368(4) -0.15630(13) 0.48364(9) 0.0517(5) Uani 1 1 d . . .
H14 H 0.5826 -0.1378 0.5004 0.062 Uiso 1 1 calc R . .
C15 C 0.5292(5) -0.31889(19) 0.49889(12) 0.0822(8) Uani 1 1 d . . .
H15A H 0.6772 -0.3021 0.5128 0.099 Uiso 1 1 calc R . .
H15B H 0.5319 -0.3818 0.4787 0.099 Uiso 1 1 calc R . .
C16 C 0.3958(3) -0.32669(14) 0.55336(8) 0.0503(5) Uani 1 1 d . . .
C17 C 0.3783(6) -0.22578(18) 0.57774(10) 0.0913(10) Uani 1 1 d . . .
H17A H 0.2803 -0.2256 0.6104 0.110 Uiso 1 1 calc R . .
H17B H 0.5197 -0.2044 0.5948 0.110 Uiso 1 1 calc R . .
C18 C 0.1779(6) -0.3695(4) 0.5335(2) 0.151(2) Uani 1 1 d . . .
H18A H 0.1968 -0.4343 0.5181 0.227 Uiso 1 1 calc R . .
H18B H 0.1076 -0.3296 0.5020 0.227 Uiso 1 1 calc R . .
H18C H 0.0902 -0.3720 0.5679 0.227 Uiso 1 1 calc R . .
C19 C 0.5108(5) -0.39188(19) 0.60229(10) 0.0766(7) Uani 1 1 d . . .
H19A H 0.5226 -0.4569 0.5865 0.115 Uiso 1 1 calc R . .
H19B H 0.4289 -0.3932 0.6379 0.115 Uiso 1 1 calc R . .
H19C H 0.6533 -0.3665 0.6132 0.115 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.267(2) . ?
N1 C7 1.397(2) . ?
N1 C1 1.494(2) . ?
N2 C7 1.280(2) . ?
N2 C2 1.492(2) . ?
O2 C14 1.388(2) . ?
O2 C15 1.436(3) . ?
O3 C14 1.377(3) . ?
O3 C17 1.444(3) . ?
C1 C4 1.519(3) . ?
C1 C3 1.525(3) . ?
C1 C2 1.552(3) . ?
C2 C6 1.522(3) . ?
C2 C5 1.529(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.477(2) . ?
C8 C13 1.390(2) . ?
C8 C9 1.390(3) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(3) . ?
C11 C14 1.507(2) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 0.9800 . ?
C15 C16 1.502(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.489(3) . ?
C16 C18 1.502(4) . ?
C16 C19 1.529(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O1 N1 C7 126.38(15) . . ?
O1 N1 C1 123.40(14) . . ?
C7 N1 C1 108.96(14) . . ?
C7 N2 C2 109.05(15) . . ?
C14 O2 C15 110.32(17) . . ?
C14 O3 C17 110.76(19) . . ?
N1 C1 C4 110.05(16) . . ?
N1 C1 C3 106.32(16) . . ?
C4 C1 C3 109.37(17) . . ?
N1 C1 C2 99.14(13) . . ?
C4 C1 C2 117.03(17) . . ?
C3 C1 C2 113.93(18) . . ?
N2 C2 C6 108.86(17) . . ?
N2 C2 C5 106.05(16) . . ?
C6 C2 C5 109.06(18) . . ?
N2 C2 C1 104.62(14) . . ?
C6 C2 C1 114.58(17) . . ?
C5 C2 C1 113.16(18) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 N1 113.06(15) . . ?
N2 C7 C8 124.83(15) . . ?
N1 C7 C8 122.05(15) . . ?
C13 C8 C9 119.23(16) . . ?
C13 C8 C7 117.77(16) . . ?
C9 C8 C7 123.00(15) . . ?
C10 C9 C8 119.92(17) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.79(18) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.25(16) . . ?
C12 C11 C14 121.72(17) . . ?
C10 C11 C14 119.02(17) . . ?
C11 C12 C13 120.41(17) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.33(18) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O3 C14 O2 110.66(17) . . ?
O3 C14 C11 110.63(17) . . ?
O2 C14 C11 107.64(15) . . ?
O3 C14 H14 109.3 . . ?
O2 C14 H14 109.3 . . ?
C11 C14 H14 109.3 . . ?
O2 C15 C16 112.42(19) . . ?
O2 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
O2 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 106.09(19) . . ?
C17 C16 C18 112.3(3) . . ?
C15 C16 C18 109.3(3) . . ?
C17 C16 C19 109.51(18) . . ?
C15 C16 C19 110.10(19) . . ?
C18 C16 C19 109.5(2) . . ?
O3 C17 C16 111.24(18) . . ?
O3 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
O3 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.854
_diffrn_reflns_theta_full        29.48
_diffrn_measured_fraction_theta_full 0.854
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.072
_database_code_depnum_ccdc_archive 'CCDC 996674'
