data_s93
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. A. K. Croft
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C17 H13 Br N2 O4'
_chemical_formula_weight          389.20
 
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    C2/c
_symmetry_space_group_name_hall   '-C 2yc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    18.884(5)
_cell_length_b                    9.725(3)
_cell_length_c                    18.447(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  112.90(3)
_cell_angle_gamma                 90.00
_cell_volume                      3120.7(14)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     6953
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Blade
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.657
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1568
_exptl_absorpt_coefficient_mu     2.659
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7769
_exptl_absorpt_correction_T_max   0.9245
_exptl_absorpt_process_details       'SADABS V2.10 (Sheldrick, G.M., 2003)'

_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             30574
_diffrn_reflns_av_R_equivalents   0.0859
_diffrn_reflns_av_sigmaI/netI     0.0626
_diffrn_reflns_limit_h_min        -24
_diffrn_reflns_limit_h_max        24
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.05
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3570
_reflns_number_gt                 2200
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   ?
 
_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)+(0.0401P)²+19.1312P] 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          3570
_refine_ls_number_parameters      236
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1506
_refine_ls_R_factor_gt            0.0898
_refine_ls_wR_factor_ref          0.1940
_refine_ls_wR_factor_gt           0.1724
_refine_ls_goodness_of_fit_ref    1.169
_refine_ls_restrained_S_all       1.169
_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
C1 C 0.1129(3) 0.3671(7) 0.1393(4) 0.0588(17) Uani 1 1 d . . .
H1 H 0.1050 0.4470 0.1029 0.071 Uiso 1 1 calc R A 1
C2 C 0.0519(3) 0.2574(6) 0.1050(3) 0.0470(14) Uani 1 1 d . C .
C3 C -0.0072(4) 0.2587(7) 0.0314(4) 0.0540(16) Uani 1 1 d . . .
H3 H -0.0118 0.3313 -0.0046 0.065 Uiso 1 1 calc R C .
C4 C -0.0595(3) 0.1516(7) 0.0116(3) 0.0527(16) Uani 1 1 d . C .
C5 C -0.0541(4) 0.0409(6) 0.0605(4) 0.0531(15) Uani 1 1 d . . .
H5 H -0.0908 -0.0314 0.0446 0.064 Uiso 1 1 calc R C .
C6 C 0.0072(3) 0.0384(6) 0.1345(4) 0.0483(14) Uani 1 1 d . C .
H6 H 0.0131 -0.0371 0.1690 0.058 Uiso 1 1 calc R . .
C7 C 0.0591(3) 0.1460(6) 0.1568(3) 0.0463(14) Uani 1 1 d . . .
C8 C 0.1260(3) 0.1613(6) 0.2334(4) 0.0524(15) Uani 1 1 d . C .
H8 H 0.1291 0.0835 0.2699 0.063 Uiso 1 1 calc R . .
C9 C 0.1171(3) 0.2971(7) 0.2676(4) 0.0543(16) Uani 1 1 d . . .
C10 C 0.1171(4) 0.3160(8) 0.3425(4) 0.0668(19) Uani 1 1 d . C .
H10 H 0.1248 0.2401 0.3771 0.080 Uiso 1 1 calc R . .
C11 C 0.1056(4) 0.4464(8) 0.3658(5) 0.0679(19) Uani 1 1 d . . .
H11 H 0.1036 0.4606 0.4159 0.081 Uiso 1 1 calc R C .
C12 C 0.0971(3) 0.5544(7) 0.3158(4) 0.0587(17) Uani 1 1 d . C .
C13 C 0.0998(3) 0.5408(7) 0.2406(4) 0.0612(18) Uani 1 1 d . . .
H13 H 0.0959 0.6186 0.2081 0.073 Uiso 1 1 calc R C .
C14 C 0.1087(3) 0.4083(6) 0.2160(4) 0.0531(16) Uani 1 1 d . C .
C16 C 0.2003(3) 0.1724(7) 0.2161(4) 0.0552(16) Uani 1 1 d . . .
H16A H 0.2078 0.0866 0.1911 0.066 Uiso 1 1 calc R B 1
H16B H 0.2456 0.1857 0.2659 0.066 Uiso 1 1 calc R B 1
N1 N -0.1245(4) 0.1541(7) -0.0655(4) 0.0702(16) Uani 1 1 d . . .
N11 N 0.0840(3) 0.6950(7) 0.3408(5) 0.079(2) Uani 1 1 d . . .
O1 O -0.1766(4) 0.0739(6) -0.0782(3) 0.0837(16) Uani 1 1 d . C .
O2 O -0.1236(3) 0.2416(7) -0.1136(3) 0.101(2) Uani 1 1 d . C .
O11 O 0.0732(3) 0.7045(6) 0.4023(4) 0.0923(18) Uani 1 1 d . C .
O12 O 0.0844(3) 0.7926(6) 0.2977(4) 0.0984(19) Uani 1 1 d . C .
C15 C 0.1922(4) 0.2980(8) 0.1596(5) 0.075(2) Uani 0.607(9) 1 d P C 1
H15 H 0.2302 0.3671 0.1928 0.090 Uiso 0.607(9) 1 calc PR C 1
C17 C 0.2151(5) 0.2701(10) 0.0985(5) 0.047(3) Uani 0.607(9) 1 d P C 1
H17A H 0.1737 0.2185 0.0572 0.057 Uiso 0.607(9) 1 calc PR C 1
H17B H 0.2611 0.2102 0.1183 0.057 Uiso 0.607(9) 1 calc PR C 1
Br1 Br 0.23940(13) 0.4346(4) 0.0508(2) 0.0614(9) Uani 0.607(9) 1 d P C 1
C20 C 0.1922(4) 0.2980(8) 0.1596(5) 0.075(2) Uani 0.393(9) 1 d P C 2
H20 H 0.1849 0.2508 0.1090 0.090 Uiso 0.393(9) 1 calc PR C 2
C21 C 0.2491(9) 0.3729(17) 0.1696(9) 0.054(4) Uani 0.393(9) 1 d P C 2
H21A H 0.2946 0.3125 0.1830 0.065 Uiso 0.393(9) 1 calc PR C 2
H21B H 0.2576 0.4316 0.2161 0.065 Uiso 0.393(9) 1 calc PR C 2
Br21 Br 0.24596(16) 0.4971(8) 0.0803(3) 0.0757(14) Uani 0.393(9) 1 d P C 2
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C14 1.502(9) . ?
C1 C2 1.516(9) . ?
C1 C15 1.549(9) . ?
C1 H1 1.0000 . ?
C2 C3 1.382(9) . ?
C2 C7 1.415(8) . ?
C3 C4 1.382(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(9) . ?
C4 N1 1.475(8) . ?
C5 C6 1.404(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.492(8) . ?
C8 C9 1.501(9) . ?
C8 C16 1.558(8) . ?
C8 H8 1.0000 . ?
C9 C10 1.394(9) . ?
C9 C14 1.407(9) . ?
C10 C11 1.383(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.365(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.416(9) . ?
C12 N11 1.493(9) . ?
C13 C14 1.397(9) . ?
C13 H13 0.9500 . ?
C16 C15 1.574(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N1 O1 1.205(8) . ?
N1 O2 1.234(8) . ?
N11 O11 1.232(8) . ?
N11 O12 1.240(9) . ?
C15 C17 1.382(11) . ?
C15 H15 1.0000 . ?
C17 Br1 1.963(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C21 Br21 2.024(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
 
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
C14 C1 C2 105.7(4) . . ?
C14 C1 C15 106.8(6) . . ?
C2 C1 C15 107.6(6) . . ?
C14 C1 H1 112.1 . . ?
C2 C1 H1 112.1 . . ?
C15 C1 H1 112.1 . . ?
C3 C2 C7 119.9(6) . . ?
C3 C2 C1 126.5(5) . . ?
C7 C2 C1 113.5(5) . . ?
C2 C3 C4 118.2(6) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 123.4(6) . . ?
C5 C4 N1 117.7(6) . . ?
C3 C4 N1 118.9(6) . . ?
C4 C5 C6 118.0(6) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C7 C6 C5 119.8(6) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 120.5(5) . . ?
C6 C7 C8 126.7(5) . . ?
C2 C7 C8 112.7(5) . . ?
C7 C8 C9 107.1(5) . . ?
C7 C8 C16 108.2(5) . . ?
C9 C8 C16 106.3(5) . . ?
C7 C8 H8 111.7 . . ?
C9 C8 H8 111.7 . . ?
C16 C8 H8 111.7 . . ?
C10 C9 C14 121.6(6) . . ?
C10 C9 C8 125.2(6) . . ?
C14 C9 C8 113.2(5) . . ?
C11 C10 C9 119.4(7) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 119.1(7) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 123.4(6) . . ?
C11 C12 N11 119.1(7) . . ?
C13 C12 N11 117.4(7) . . ?
C14 C13 C12 117.3(6) . . ?
C14 C13 H13 121.4 . . ?
C12 C13 H13 121.4 . . ?
C13 C14 C9 119.1(6) . . ?
C13 C14 C1 127.5(6) . . ?
C9 C14 C1 113.4(5) . . ?
C8 C16 C15 109.0(5) . . ?
C8 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
C8 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O1 N1 O2 123.1(7) . . ?
O1 N1 C4 119.2(6) . . ?
O2 N1 C4 117.7(7) . . ?
O11 N11 O12 125.3(7) . . ?
O11 N11 C12 117.3(7) . . ?
O12 N11 C12 117.5(7) . . ?
C17 C15 C1 118.0(7) . . ?
C17 C15 C16 114.0(7) . . ?
C1 C15 C16 109.4(5) . . ?
C17 C15 H15 104.7 . . ?
C1 C15 H15 104.7 . . ?
C16 C15 H15 104.7 . . ?
C15 C17 Br1 114.0(7) . . ?
C15 C17 H17A 108.8 . . ?
Br1 C17 H17A 108.8 . . ?
C15 C17 H17B 108.8 . . ?
Br1 C17 H17B 108.8 . . ?
H17A C17 H17B 107.6 . . ?
Br21 C21 H21A 107.7 . . ?
Br21 C21 H21B 107.7 . . ?
H21A C21 H21B 107.1 . . ?
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.520
_refine_diff_density_min   -0.304
_refine_diff_density_rms    0.070
