
# ol991038n.cif

data_brnn

_audit_creation_method            SHELXL
_chemical_name_systematic
rel-(1S,2R,3S,6R)-6-Azido-2-bromo-4-cyclohexene-1,3-diol
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C6 H8 Br N3 O2'
_chemical_formula_weight          234.05
_chemical_melting_point           97 - 98
_chemical_compound_source         ?

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)/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                    17.6335(11)
_cell_length_b                    11.7727(8)
_cell_length_c                    8.5975(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  100.718(2)
_cell_angle_gamma                 90.00
_cell_volume                      1753.7(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     295(2)
_cell_measurement_reflns_used     4382
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        'plate'
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.40
_exptl_crystal_size_min           0.16
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.773
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              928
_exptl_absorpt_coefficient_mu     4.652
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
 ?
;

_diffrn_ambient_temperature       295(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        'Bruker P4/CCD'
_diffrn_measurement_method        'SMART CCD'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             99388
_diffrn_reflns_av_R_equivalents   0.096
_diffrn_reflns_av_sigmaI/netI     0.1313
_diffrn_reflns_limit_h_min        -22
_diffrn_reflns_limit_h_max        21
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          1.18
_diffrn_reflns_theta_max          28.20
_reflns_number_total              3718
_reflns_number_observed           2120
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        'Bruker SMART'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics     SHELXTL-Plus
_computing_publication_material   SHELXL-93

_refine_special_details
;
 Refinement on F² for ALL reflections except for 2 with very negative F²
 or flagged by the user for potential systematic errors.  Weighted R-factors
 wR and all goodnesses of fit S are based on F², conventional R-factors R
 are based on F, with F set to zero for negative F². The observed criterion
 of F² > 2sigma(F²) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     ?
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        0.0004(3)
_refine_ls_number_reflns          3716
_refine_ls_number_parameters      261
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0988
_refine_ls_R_factor_obs           0.0553
_refine_ls_wR_factor_all          0.1252
_refine_ls_wR_factor_obs          0.1155
_refine_ls_goodness_of_fit_all    0.906
_refine_ls_goodness_of_fit_obs    1.149
_refine_ls_restrained_S_all       0.917
_refine_ls_restrained_S_obs       1.149
_refine_ls_shift/esd_max          0.007
_refine_ls_shift/esd_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_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
Br1 Br 0.10321(4) 0.04124(5) 0.17727(7) 0.0411(2) Uani 1 d . .
C1 C 0.1856(4) 0.0601(4) 0.3643(7) 0.0289(14) Uani 1 d . .
C2 C 0.1689(4) 0.1651(5) 0.4580(7) 0.0327(14) Uani 1 d . .
C3 C 0.1127(4) 0.1405(5) 0.5658(7) 0.0360(15) Uani 1 d . .
C4 C 0.0918(3) 0.0377(5) 0.5996(7) 0.0335(14) Uani 1 d . .
C5 C 0.1206(4) -0.0689(4) 0.5312(7) 0.0303(14) Uani 1 d . .
C6 C 0.1927(3) -0.0464(4) 0.4652(7) 0.0251(13) Uani 1 d . .
O1 O 0.2393(3) 0.2016(4) 0.5559(5) 0.0421(12) Uani 1 d . .
N1 N 0.1405(3) -0.1581(4) 0.6562(6) 0.051(2) Uani 1 d . .
N2 N 0.0844(4) -0.1990(5) 0.6969(9) 0.084(3) Uani 1 d . .
N3 N 0.0370(5) -0.2444(8) 0.7439(15) 0.182(6) Uani 1 d . .
O2 O 0.2125(3) -0.1391(3) 0.3750(4) 0.0387(11) Uani 1 d . .
H02 H 0.2321(30) -0.1897(20) 0.4348(5) 0.046 Uiso 1 calc R .
Br2 Br 0.38662(4) 0.40138(5) 0.71162(7) 0.0408(2) Uani 1 d . .
C7 C 0.3125(4) 0.4983(5) 0.5696(6) 0.0298(13) Uani 1 d . .
C8 C 0.3287(4) 0.6221(5) 0.6160(7) 0.0341(14) Uani 1 d . .
C9 C 0.3864(4) 0.6757(5) 0.5293(7) 0.039(2) Uani 1 d . .
C10 C 0.4156(4) 0.6260(5) 0.4186(7) 0.037(2) Uani 1 d . .
C11 C 0.3938(3) 0.5068(5) 0.3623(6) 0.0288(13) Uani 1 d . .
C12 C 0.3161(3) 0.4747(5) 0.3974(7) 0.0286(13) Uani 1 d . .
O3 O 0.2581(3) 0.6841(4) 0.5741(6) 0.056(2) Uani 1 d . .
N4 N 0.3891(3) 0.5012(5) 0.1862(5) 0.0409(13) Uani 1 d . .
N5 N 0.4337(3) 0.4317(4) 0.1435(6) 0.0420(13) Uani 1 d . .
N6 N 0.4719(4) 0.3719(5) 0.0913(7) 0.074(2) Uani 1 d . .
O4 O 0.2970(3) 0.3586(3) 0.3618(5) 0.0437(11) Uani 1 d . .
H04 H 0.3107(32) 0.3198(8) 0.4412(20) 0.052 Uiso 1 calc R .
H1 H 0.2312(31) 0.0731(40) 0.3158(65) 0.030 Uiso 1 d . .
H2 H 0.1520(25) 0.2325(39) 0.3780(57) 0.021 Uiso 1 d . .
H3 H 0.0853(31) 0.2110(48) 0.6012(66) 0.044 Uiso 1 d . .
H4 H 0.0544(35) 0.0306(48) 0.6719(77) 0.053 Uiso 1 d . .
H5 H 0.0745(30) -0.0950(42) 0.4280(66) 0.035 Uiso 1 d . .
H6 H 0.2321(35) -0.0372(48) 0.5384(79) 0.044 Uiso 1 d . .
H01 H 0.2640(33) 0.2369(49) 0.5083(71) 0.034 Uiso 1 d . .
H7 H 0.2602(26) 0.4744(34) 0.5878(49) 0.005 Uiso 1 d . .
H8 H 0.3515(35) 0.6315(53) 0.7387(85) 0.066 Uiso 1 d . .
H9 H 0.4024(28) 0.7530(44) 0.5596(62) 0.036 Uiso 1 d . .
H10 H 0.4557(32) 0.6662(44) 0.3905(64) 0.036 Uiso 1 d . .
H11 H 0.4343(31) 0.4527(42) 0.4082(66) 0.031 Uiso 1 d . .
H12 H 0.2779(34) 0.5267(49) 0.3355(76) 0.050 Uiso 1 d . .
H03 H 0.2312(42) 0.6683(62) 0.6171(82) 0.051 Uiso 1 d . .


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

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Br1 C1 1.969(6) . ?
C1 C6 1.517(7) . ?
C1 C2 1.534(7) . ?
C2 O1 1.430(7) . ?
C2 C3 1.506(8) . ?
C3 C4 1.313(8) . ?
C4 C5 1.512(7) . ?
C5 N1 1.497(7) . ?
C5 C6 1.508(8) . ?
C6 O2 1.419(6) . ?
N1 N2 1.209(8) . ?
N2 N3 1.128(9) . ?
Br2 C7 1.977(5) . ?
C7 C12 1.519(7) . ?
C7 C8 1.523(8) . ?
C8 O3 1.430(8) . ?
C8 C9 1.508(8) . ?
C9 C10 1.303(8) . ?
C10 C11 1.511(8) . ?
C11 N4 1.502(7) . ?
C11 C12 1.504(8) . ?
C12 O4 1.427(6) . ?
N4 N5 1.237(7) . ?
N5 N6 1.124(7) . ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C6 C1 C2 111.7(4) . . ?
C6 C1 Br1 110.1(4) . . ?
C2 C1 Br1 109.6(4) . . ?
O1 C2 C3 107.1(5) . . ?
O1 C2 C1 108.7(5) . . ?
C3 C2 C1 112.4(5) . . ?
C4 C3 C2 123.9(5) . . ?
C3 C4 C5 123.4(5) . . ?
N1 C5 C6 107.0(5) . . ?
N1 C5 C4 110.7(5) . . ?
C6 C5 C4 111.6(5) . . ?
O2 C6 C5 112.4(4) . . ?
O2 C6 C1 109.0(4) . . ?
C5 C6 C1 112.0(5) . . ?
N2 N1 C5 113.2(6) . . ?
N3 N2 N1 173.1(8) . . ?
C12 C7 C8 113.0(5) . . ?
C12 C7 Br2 110.7(4) . . ?
C8 C7 Br2 108.7(4) . . ?
O3 C8 C9 107.3(5) . . ?
O3 C8 C7 108.1(5) . . ?
C9 C8 C7 112.4(5) . . ?
C10 C9 C8 124.6(6) . . ?
C9 C10 C11 122.7(6) . . ?
N4 C11 C12 108.1(5) . . ?
N4 C11 C10 109.0(4) . . ?
C12 C11 C10 110.9(4) . . ?
O4 C12 C11 112.6(4) . . ?
O4 C12 C7 109.5(4) . . ?
C11 C12 C7 110.8(5) . . ?
N5 N4 C11 114.1(5) . . ?
N6 N5 N4 173.8(6) . . ?

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
 C6 C1 C2 O1 78.4(6) . . . . ?
 Br1 C1 C2 O1 -159.3(3) . . . . ?
 C6 C1 C2 C3 -40.0(7) . . . . ?
 Br1 C1 C2 C3 82.3(5) . . . . ?
 O1 C2 C3 C4 -106.9(7) . . . . ?
 C1 C2 C3 C4 12.4(9) . . . . ?
 C2 C3 C4 C5 -1.4(10) . . . . ?
 C3 C4 C5 N1 137.3(6) . . . . ?
 C3 C4 C5 C6 18.2(9) . . . . ?
 N1 C5 C6 O2 69.7(6) . . . . ?
 C4 C5 C6 O2 -169.1(5) . . . . ?
 N1 C5 C6 C1 -167.2(5) . . . . ?
 C4 C5 C6 C1 -46.0(7) . . . . ?
 C2 C1 C6 O2 -176.7(5) . . . . ?
 Br1 C1 C6 O2 61.4(5) . . . . ?
 C2 C1 C6 C5 58.3(7) . . . . ?
 Br1 C1 C6 C5 -63.6(5) . . . . ?
 C6 C5 N1 N2 -166.7(6) . . . . ?
 C4 C5 N1 N2 71.5(8) . . . . ?
 C5 N1 N2 N3 175.1(86) . . . . ?
 C12 C7 C8 O3 84.6(6) . . . . ?
 Br2 C7 C8 O3 -152.1(4) . . . . ?
 C12 C7 C8 C9 -33.6(7) . . . . ?
 Br2 C7 C8 C9 89.7(5) . . . . ?
 O3 C8 C9 C10 -114.0(7) . . . . ?
 C7 C8 C9 C10 4.7(9) . . . . ?
 C8 C9 C10 C11 0.6(11) . . . . ?
 C9 C10 C11 N4 141.8(6) . . . . ?
 C9 C10 C11 C12 22.9(9) . . . . ?
 N4 C11 C12 O4 66.9(6) . . . . ?
 C10 C11 C12 O4 -173.7(4) . . . . ?
 N4 C11 C12 C7 -170.1(5) . . . . ?
 C10 C11 C12 C7 -50.7(6) . . . . ?
 C8 C7 C12 O4 -177.4(5) . . . . ?
 Br2 C7 C12 O4 60.4(6) . . . . ?
 C8 C7 C12 C11 57.8(6) . . . . ?
 Br2 C7 C12 C11 -64.4(5) . . . . ?
 C12 C11 N4 N5 -119.0(6) . . . . ?
 C10 C11 N4 N5 120.5(6) . . . . ?
 C11 N4 N5 N6 -176.8(65) . . . . ?

_refine_diff_density_max    1.608
_refine_diff_density_min   -1.018
_refine_diff_density_rms    0.169

#===END

data_benk

_audit_creation_method            SHELXL
_chemical_name_systematic
rel-(1S,2S,3S,4R,5S,6S)-4-Azido-2-bromo-5,6-epoxycyclohexane-1,3-diol
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C6 H8 Br N3 O3'
_chemical_formula_weight          250.05
_chemical_melting_point           131 -132
_chemical_compound_source         ?

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)/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                    17.4244(10)
_cell_length_b                    11.7782(6)
_cell_length_c                    8.6105(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.5310(10)
_cell_angle_gamma                 90.00
_cell_volume                      1765.4(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     295(2)
_cell_measurement_reflns_used     3601
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        'cut fragment'
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.22
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.882
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              992
_exptl_absorpt_coefficient_mu     4.636
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
 ?
;

_diffrn_ambient_temperature       295(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        'Bruker P4/CCD'
_diffrn_measurement_method        'SMART CCD'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             9747
_diffrn_reflns_av_R_equivalents   0.045
_diffrn_reflns_av_sigmaI/netI     0.0564
_diffrn_reflns_limit_h_min        -21
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          1.17
_diffrn_reflns_theta_max          28.25
_reflns_number_total              3794
_reflns_number_observed           2814
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        'Bruker SMART'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics     SHELXTL-Plus
_computing_publication_material   SHELXL-93

_refine_special_details
;
 Refinement on F² for ALL reflections except for 2 with very negative F²
 or flagged by the user for potential systematic errors.  Weighted R-factors
 wR and all goodnesses of fit S are based on F², conventional R-factors R
 are based on F, with F set to zero for negative F². The observed criterion
 of F² > 2sigma(F²) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     ?
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0000(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3792
_refine_ls_number_parameters      300
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0562
_refine_ls_R_factor_obs           0.0347
_refine_ls_wR_factor_all          0.0794
_refine_ls_wR_factor_obs          0.0731
_refine_ls_goodness_of_fit_all    0.940
_refine_ls_goodness_of_fit_obs    1.027
_refine_ls_restrained_S_all       0.948
_refine_ls_restrained_S_obs       1.027
_refine_ls_shift/esd_max          -5.688
_refine_ls_shift/esd_mean         0.019

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_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
Br1 Br 0.11445(2) 0.09760(3) 0.25258(3) 0.03563(12) Uani 1 d . .
C1 C 0.1906(2) 0.0115(2) 0.1378(3) 0.0244(6) Uani 1 d . .
C2 C 0.1822(2) 0.0355(2) -0.0342(3) 0.0241(6) Uani 1 d . .
C3 C 0.1047(2) -0.0030(3) -0.1031(3) 0.0285(7) Uani 1 d . .
C4 C 0.0886(2) -0.1245(3) -0.0598(4) 0.0350(8) Uani 1 d . .
C5 C 0.1266(2) -0.1777(3) 0.0755(4) 0.0372(8) Uani 1 d . .
C6 C 0.1836(2) -0.1142(3) 0.1804(4) 0.0302(7) Uani 1 d . .
O1 O 0.19141(15) 0.1539(2) -0.0598(3) 0.0337(6) Uani 1 d . .
N1 N 0.1059(2) 0.0024(3) -0.2757(3) 0.0428(7) Uani 1 d . .
N2 N 0.0621(2) 0.0731(3) -0.3364(3) 0.0405(7) Uani 1 d . .
N3 N 0.0242(3) 0.1324(3) -0.4055(4) 0.0731(12) Uani 1 d . .
O2 O 0.15188(14) -0.2007(2) -0.0774(3) 0.0445(6) Uani 1 d . .
O3 O 0.2560(2) -0.1681(2) 0.1695(3) 0.0407(6) Uani 1 d . .
Br2 Br 0.39501(2) 0.04209(3) 0.35020(4) 0.03853(12) Uani 1 d . .
C7 C 0.3144(2) 0.0562(3) 0.5032(3) 0.0263(7) Uani 1 d . .
C8 C 0.3118(2) -0.0510(2) 0.5992(3) 0.0256(7) Uani 1 d . .
C9 C 0.3861(2) -0.0689(3) 0.6935(4) 0.0279(7) Uani 1 d . .
C10 C 0.4143(2) 0.0351(3) 0.7779(4) 0.0304(7) Uani 1 d . .
C11 C 0.3863(2) 0.1487(3) 0.7313(4) 0.0344(8) Uani 1 d . .
C12 C 0.3282(2) 0.1650(3) 0.5980(4) 0.0308(7) Uani 1 d . .
O4 O 0.2951(2) -0.1435(2) 0.4982(3) 0.0362(6) Uani 1 d . .
N4 N 0.3713(2) -0.1633(2) 0.8038(3) 0.0465(8) Uani 1 d . .
N5 N 0.4239(2) -0.1855(3) 0.8956(4) 0.0515(9) Uani 1 d . .
N6 N 0.4687(3) -0.2125(4) 0.9867(5) 0.099(2) Uani 1 d . .
O5 O 0.35710(14) 0.0922(2) 0.8658(2) 0.0384(6) Uani 1 d . .
O6 O 0.2583(2) 0.2008(2) 0.6611(3) 0.0414(6) Uani 1 d . .
H1 H 0.2391(18) 0.0365(24) 0.1829(32) 0.023(8) Uiso 1 d . .
H2 H 0.2187(15) 0.0002(22) -0.0802(28) 0.004(6) Uiso 1 d . .
H3 H 0.0654(17) 0.0434(24) -0.0659(32) 0.018(7) Uiso 1 d . .
H4 H 0.0430(19) -0.1500(26) -0.1029(35) 0.030(9) Uiso 1 d . .
H5 H 0.1008(20) -0.2375(33) 0.1162(41) 0.050(11) Uiso 1 d . .
H6 H 0.1695(18) -0.1218(25) 0.2772(36) 0.027(8) Uiso 1 d . .
H01 H 0.2119(20) 0.1652(29) -0.1299(38) 0.030(11) Uiso 1 d . .
H03 H 0.2769(24) -0.1601(36) 0.2422(43) 0.050(14) Uiso 1 d . .
H7 H 0.2668(18) 0.0641(24) 0.4421(33) 0.022(8) Uiso 1 d . .
H8 H 0.2704(17) -0.0411(22) 0.6727(32) 0.018(7) Uiso 1 d . .
H9 H 0.4260(16) -0.0889(22) 0.6285(31) 0.012(7) Uiso 1 d . .
H10 H 0.4636(18) 0.0284(23) 0.8307(32) 0.021(8) Uiso 1 d . .
H11 H 0.4220(19) 0.2086(29) 0.7538(36) 0.037(9) Uiso 1 d . .
H12 H 0.3473(16) 0.2127(25) 0.5384(32) 0.017(8) Uiso 1 d . .
H04 H 0.2784(23) -0.1874(33) 0.5443(42) 0.044(13) Uiso 1 d . .
H06 H 0.2344(21) 0.2317(31) 0.5999(41) 0.036(11) Uiso 1 d . .


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

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Br1 C1 1.971(3) . ?
C1 C2 1.508(4) . ?
C1 C6 1.532(4) . ?
C2 O1 1.422(4) . ?
C2 C3 1.520(4) . ?
C3 N1 1.488(4) . ?
C3 C4 1.509(5) . ?
C4 O2 1.435(4) . ?
C4 C5 1.457(5) . ?
C5 O2 1.433(4) . ?
C5 C6 1.510(5) . ?
C6 O3 1.420(4) . ?
N1 N2 1.230(4) . ?
N2 N3 1.116(4) . ?
Br2 C7 1.974(3) . ?
C7 C8 1.511(4) . ?
C7 C12 1.533(4) . ?
C8 O4 1.416(4) . ?
C8 C9 1.513(4) . ?
C9 N4 1.492(4) . ?
C9 C10 1.496(4) . ?
C10 O5 1.444(4) . ?
C10 C11 1.474(5) . ?
C11 O5 1.447(4) . ?
C11 C12 1.509(5) . ?
C12 O6 1.419(4) . ?
N4 N5 1.213(4) . ?
N5 N6 1.127(4) . ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 C6 114.3(2) . . ?
C2 C1 Br1 110.9(2) . . ?
C6 C1 Br1 108.3(2) . . ?
O1 C2 C1 109.2(2) . . ?
O1 C2 C3 109.7(3) . . ?
C1 C2 C3 112.0(3) . . ?
N1 C3 C4 107.3(3) . . ?
N1 C3 C2 109.0(3) . . ?
C4 C3 C2 111.0(3) . . ?
O2 C4 C5 59.4(2) . . ?
O2 C4 C3 114.5(3) . . ?
C5 C4 C3 121.5(3) . . ?
O2 C5 C4 59.6(2) . . ?
O2 C5 C6 115.0(3) . . ?
C4 C5 C6 121.9(3) . . ?
O3 C6 C5 107.6(3) . . ?
O3 C6 C1 109.6(3) . . ?
C5 C6 C1 113.2(3) . . ?
N2 N1 C3 114.6(3) . . ?
N3 N2 N1 172.9(4) . . ?
C5 O2 C4 61.1(2) . . ?
C8 C7 C12 114.5(2) . . ?
C8 C7 Br2 109.6(2) . . ?
C12 C7 Br2 109.0(2) . . ?
O4 C8 C7 108.5(2) . . ?
O4 C8 C9 111.7(3) . . ?
C7 C8 C9 111.4(3) . . ?
N4 C9 C10 111.3(3) . . ?
N4 C9 C8 106.1(3) . . ?
C10 C9 C8 113.7(3) . . ?
O5 C10 C11 59.4(2) . . ?
O5 C10 C9 114.6(3) . . ?
C11 C10 C9 120.9(3) . . ?
O5 C11 C10 59.3(2) . . ?
O5 C11 C12 114.8(3) . . ?
C10 C11 C12 121.7(3) . . ?
O6 C12 C11 107.7(3) . . ?
O6 C12 C7 109.6(3) . . ?
C11 C12 C7 112.5(3) . . ?
N5 N4 C9 115.4(3) . . ?
N6 N5 N4 174.1(4) . . ?
C10 O5 C11 61.3(2) . . ?

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
 C6 C1 C2 O1 -178.7(3) . . . . ?
 Br1 C1 C2 O1 58.5(3) . . . . ?
 C6 C1 C2 C3 59.6(4) . . . . ?
 Br1 C1 C2 C3 -63.2(3) . . . . ?
 O1 C2 C3 N1 69.5(3) . . . . ?
 C1 C2 C3 N1 -169.1(3) . . . . ?
 O1 C2 C3 C4 -172.5(2) . . . . ?
 C1 C2 C3 C4 -51.1(3) . . . . ?
 N1 C3 C4 O2 73.4(3) . . . . ?
 C2 C3 C4 O2 -45.6(4) . . . . ?
 N1 C3 C4 C5 141.3(3) . . . . ?
 C2 C3 C4 C5 22.3(4) . . . . ?
 O2 C4 C5 O2 0.0 . . . . ?
 C3 C4 C5 O2 -101.7(3) . . . . ?
 O2 C4 C5 C6 102.2(4) . . . . ?
 C3 C4 C5 C6 0.5(5) . . . . ?
 O2 C5 C6 O3 -47.6(4) . . . . ?
 C4 C5 C6 O3 -116.0(3) . . . . ?
 O2 C5 C6 C1 73.6(4) . . . . ?
 C4 C5 C6 C1 5.2(5) . . . . ?
 C2 C1 C6 O3 85.3(3) . . . . ?
 Br1 C1 C6 O3 -150.5(2) . . . . ?
 C2 C1 C6 C5 -34.7(4) . . . . ?
 Br1 C1 C6 C5 89.5(3) . . . . ?
 C4 C3 N1 N2 125.6(3) . . . . ?
 C2 C3 N1 N2 -114.2(3) . . . . ?
 C3 N1 N2 N3 -171.0(32) . . . . ?
 C4 C5 O2 C4 0.0 . . . . ?
 C6 C5 O2 C4 -113.8(3) . . . . ?
 C5 C4 O2 C5 0.0 . . . . ?
 C3 C4 O2 C5 113.4(3) . . . . ?
 C12 C7 C8 O4 177.2(3) . . . . ?
 Br2 C7 C8 O4 -59.9(3) . . . . ?
 C12 C7 C8 C9 -59.4(4) . . . . ?
 Br2 C7 C8 C9 63.4(3) . . . . ?
 O4 C8 C9 N4 -68.9(3) . . . . ?
 C7 C8 C9 N4 169.6(3) . . . . ?
 O4 C8 C9 C10 168.5(3) . . . . ?
 C7 C8 C9 C10 47.0(4) . . . . ?
 N4 C9 C10 O5 -70.7(4) . . . . ?
 C8 C9 C10 O5 49.1(4) . . . . ?
 N4 C9 C10 C11 -138.5(3) . . . . ?
 C8 C9 C10 C11 -18.8(4) . . . . ?
 O5 C10 C11 O5 0.000(1) . . . . ?
 C9 C10 C11 O5 102.2(3) . . . . ?
 O5 C10 C11 C12 -101.9(3) . . . . ?
 C9 C10 C11 C12 0.2(5) . . . . ?
 O5 C11 C12 O6 42.6(4) . . . . ?
 C10 C11 C12 O6 110.6(3) . . . . ?
 O5 C11 C12 C7 -78.2(3) . . . . ?
 C10 C11 C12 C7 -10.3(4) . . . . ?
 C8 C7 C12 O6 -80.0(3) . . . . ?
 Br2 C7 C12 O6 156.8(2) . . . . ?
 C8 C7 C12 C11 39.8(4) . . . . ?
 Br2 C7 C12 C11 -83.4(3) . . . . ?
 C10 C9 N4 N5 -52.0(4) . . . . ?
 C8 C9 N4 N5 -176.1(3) . . . . ?
 C9 N4 N5 N6 173.9(45) . . . . ?
 C11 C10 O5 C11 0.000(1) . . . . ?
 C9 C10 O5 C11 -112.6(3) . . . . ?
 C10 C11 O5 C10 0.0 . . . . ?
 C12 C11 O5 C10 113.5(3) . . . . ?

_refine_diff_density_max    0.935
_refine_diff_density_min   -0.392
_refine_diff_density_rms    0.107

#===END

