data_03sot024
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Phil Gale
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H12 Br3 N3'
_chemical_formula_weight          462.00
 
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'
 '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    P21/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                    17.13(4)
_cell_length_b                    10.965(8)
_cell_length_c                    17.450(15)
_cell_angle_alpha                 90.00
_cell_angle_beta                  114.25(7)
_cell_angle_gamma                 90.00
_cell_volume                      2989(7)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.03
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     2.053
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1776
_exptl_absorpt_coefficient_mu     8.090
_exptl_absorpt_correction_type    Multi-scans
_exptl_absorpt_correction_T_min   0.4984
_exptl_absorpt_correction_T_max   0.7934
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker Nonius Kappa CCD Area detector'
_diffrn_measurement_method        'φ and ω scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean  '9.091 pixels mm^1^'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             13791
_diffrn_reflns_av_R_equivalents   0.0742
_diffrn_reflns_av_sigmaI/netI     0.0810
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        20
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          4.90
_diffrn_reflns_theta_max          25.03
_reflns_number_total              3468
_reflns_number_gt                 2351
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO (Otwinowski and MInor, 1997)'
_computing_data_reduction         'DENZO, COLLECT, MAXUS (Mackay et al., 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)'
 
_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)+(0.0488P)²+2.3714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.00032(17)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3468
_refine_ls_number_parameters      364
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0915
_refine_ls_R_factor_gt            0.0480
_refine_ls_wR_factor_ref          0.1081
_refine_ls_wR_factor_gt           0.0952
_refine_ls_goodness_of_fit_ref    1.043
_refine_ls_restrained_S_all       1.043
_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
Br1 Br 0.09245(7) -0.09399(9) -0.03799(6) 0.0439(3) Uani 1 1 d . . .
Br2 Br 0.09172(7) -0.38805(8) 0.06020(6) 0.0392(3) Uani 1 1 d . . .
Br3 Br 0.13529(6) -0.32371(7) 0.27499(6) 0.0302(3) Uani 1 1 d . . .
N1 N 0.1236(4) -0.0354(6) 0.1292(4) 0.0178(15) Uani 1 1 d . . .
H1 H 0.1256 0.0428 0.1188 0.021 Uiso 1 1 calc R . .
N2 N 0.2206(5) -0.0175(7) 0.4356(5) 0.044(2) Uani 1 1 d . . .
H2 H 0.1827 0.0262 0.4456 0.053 Uiso 1 1 calc R . .
N3 N 0.2358(4) 0.1743(5) 0.2742(4) 0.0208(17) Uani 1 1 d . . .
H3 H 0.2836 0.1319 0.2944 0.025 Uiso 1 1 calc R . .
C1 C 0.1090(5) -0.1256(8) 0.0712(5) 0.027(2) Uani 1 1 d . . .
C2 C 0.1107(5) -0.2338(7) 0.1109(5) 0.021(2) Uani 1 1 d . . .
C3 C 0.1272(5) -0.2060(6) 0.1943(5) 0.0169(18) Uani 1 1 d . . .
C4 C 0.1348(5) -0.0818(7) 0.2051(5) 0.0199(19) Uani 1 1 d . . .
C5 C 0.1436(5) -0.0010(7) 0.2781(5) 0.0201(19) Uani 1 1 d . . .
C6 C 0.0584(5) -0.0138(7) 0.2881(5) 0.027(2) Uani 1 1 d . . .
H6A H 0.0106 0.0091 0.2354 0.040 Uiso 1 1 calc R . .
H6B H 0.0593 0.0399 0.3334 0.040 Uiso 1 1 calc R . .
H6C H 0.0512 -0.0985 0.3020 0.040 Uiso 1 1 calc R . .
C7 C 0.2169(5) -0.0438(7) 0.3573(5) 0.022(2) Uani 1 1 d . . .
C8 C 0.2911(8) -0.0689(10) 0.4948(7) 0.059(3) Uani 1 1 d . . .
H8 H 0.3087 -0.0623 0.5538 0.071 Uiso 1 1 calc R . .
C9 C 0.3319(6) -0.1300(8) 0.4569(7) 0.051(3) Uani 1 1 d . . .
H9 H 0.3824 -0.1770 0.4840 0.061 Uiso 1 1 calc R . .
C10 C 0.2863(5) -0.1129(7) 0.3669(6) 0.030(2) Uani 1 1 d . . .
H10 H 0.3016 -0.1434 0.3240 0.036 Uiso 1 1 calc R . .
C11 C 0.1563(5) 0.1300(7) 0.2602(5) 0.0169(18) Uani 1 1 d . . .
C12 C 0.0990(6) 0.2245(7) 0.2283(5) 0.024(2) Uani 1 1 d . . .
H12 H 0.0389 0.2209 0.2118 0.028 Uiso 1 1 calc R . .
C13 C 0.1467(6) 0.3274(7) 0.2250(5) 0.024(2) Uani 1 1 d . . .
H13 H 0.1243 0.4066 0.2068 0.029 Uiso 1 1 calc R . .
C14 C 0.2294(7) 0.2944(7) 0.2522(5) 0.025(2) Uani 1 1 d . . .
H14 H 0.2754 0.3457 0.2555 0.029 Uiso 1 1 calc R . .
Br4 Br 0.32169(7) -0.07851(10) 0.15017(7) 0.0480(3) Uani 1 1 d . . .
Br5 Br 0.53109(6) -0.08626(8) 0.31463(5) 0.0325(3) Uani 1 1 d . . .
Br6 Br 0.66315(6) 0.11606(8) 0.25310(6) 0.0320(3) Uani 1 1 d . . .
N4 N 0.4986(4) 0.1328(5) 0.1199(4) 0.0201(16) Uani 1 1 d . . .
H4 H 0.5175 0.1832 0.0922 0.024 Uiso 1 1 calc R . .
N5 N 0.1970(4) 0.1852(6) -0.0695(4) 0.0222(18) Uani 1 1 d . . .
H5 H 0.1912 0.1630 -0.1200 0.027 Uiso 1 1 calc R . .
N6 N 0.3897(4) 0.3235(6) -0.0348(4) 0.0234(16) Uani 1 1 d . . .
H6 H 0.3651 0.3636 -0.0070 0.028 Uiso 1 1 calc R . .
C15 C 0.5454(5) 0.0865(7) 0.1968(5) 0.0199(19) Uani 1 1 d . . .
C16 C 0.4955(5) 0.0109(7) 0.2190(5) 0.023(2) Uani 1 1 d . . .
C17 C 0.4135(5) 0.0145(7) 0.1521(5) 0.0200(19) Uani 1 1 d . . .
C18 C 0.4157(5) 0.0880(6) 0.0916(5) 0.0167(18) Uani 1 1 d . . .
C19 C 0.3509(5) 0.1157(6) 0.0016(5) 0.0181(18) Uani 1 1 d . . .
C20 C 0.3283(5) -0.0059(7) -0.0463(5) 0.026(2) Uani 1 1 d . . .
H20A H 0.3070 -0.0633 -0.0163 0.039 Uiso 1 1 calc R . .
H20B H 0.3795 -0.0398 -0.0502 0.039 Uiso 1 1 calc R . .
H20C H 0.2840 0.0078 -0.1030 0.039 Uiso 1 1 calc R . .
C21 C 0.2711(5) 0.1734(7) 0.0031(5) 0.0219(19) Uani 1 1 d . . .
C22 C 0.2546(6) 0.2195(8) 0.0677(6) 0.032(2) Uani 1 1 d . . .
H22 H 0.2939 0.2247 0.1250 0.038 Uiso 1 1 calc R . .
C23 C 0.1673(6) 0.2586(8) 0.0332(5) 0.029(2) Uani 1 1 d . . .
H23 H 0.1372 0.2938 0.0629 0.034 Uiso 1 1 calc R . .
C24 C 0.1357(5) 0.2349(7) -0.0516(5) 0.025(2) Uani 1 1 d . . .
H24 H 0.0791 0.2515 -0.0912 0.030 Uiso 1 1 calc R . .
C25 C 0.3918(5) 0.2007(6) -0.0409(5) 0.0187(19) Uani 1 1 d . . .
C26 C 0.4364(5) 0.1731(7) -0.0870(5) 0.0207(19) Uani 1 1 d . . .
H26 H 0.4487 0.0935 -0.1005 0.025 Uiso 1 1 calc R . .
C27 C 0.4616(5) 0.2847(7) -0.1118(5) 0.029(2) Uani 1 1 d . . .
H27 H 0.4933 0.2937 -0.1452 0.034 Uiso 1 1 calc R . .
C28 C 0.4315(5) 0.3761(7) -0.0785(5) 0.025(2) Uani 1 1 d . . .
H28 H 0.4384 0.4611 -0.0844 0.031 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Br1 C1 1.840(9) . ?
Br2 C2 1.874(7) . ?
Br3 C3 1.873(7) . ?
N1 C4 1.357(10) . ?
N1 C1 1.363(10) . ?
N2 C8 1.349(13) . ?
N2 C7 1.372(10) . ?
N3 C14 1.363(10) . ?
N3 C11 1.369(10) . ?
C1 C2 1.369(10) . ?
C2 C3 1.397(10) . ?
C3 C4 1.374(10) . ?
C4 C5 1.506(11) . ?
C5 C11 1.505(10) . ?
C5 C7 1.511(10) . ?
C5 C6 1.547(11) . ?
C7 C10 1.360(11) . ?
C8 C9 1.323(15) . ?
C9 C10 1.450(13) . ?
C11 C12 1.378(10) . ?
C12 C13 1.408(11) . ?
C13 C14 1.347(12) . ?
Br4 C17 1.864(8) . ?
Br5 C16 1.859(8) . ?
Br6 C15 1.874(9) . ?
N4 C15 1.347(9) . ?
N4 C18 1.388(10) . ?
N5 C24 1.328(10) . ?
N5 C21 1.383(10) . ?
N6 C25 1.352(9) . ?
N6 C28 1.371(10) . ?
C15 C16 1.357(10) . ?
C16 C17 1.411(11) . ?
C17 C18 1.340(10) . ?
C18 C19 1.536(11) . ?
C19 C21 1.517(11) . ?
C19 C25 1.527(10) . ?
C19 C20 1.537(10) . ?
C21 C22 1.367(11) . ?
C22 C23 1.429(12) . ?
C23 C24 1.376(11) . ?
C25 C26 1.353(10) . ?
C26 C27 1.424(11) . ?
C27 C28 1.362(11) . ?
 
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
C4 N1 C1 111.3(7) . . ?
C8 N2 C7 109.6(9) . . ?
C14 N3 C11 109.5(7) . . ?
N1 C1 C2 107.0(7) . . ?
N1 C1 Br1 122.4(6) . . ?
C2 C1 Br1 130.6(6) . . ?
C1 C2 C3 106.9(6) . . ?
C1 C2 Br2 125.4(6) . . ?
C3 C2 Br2 127.7(6) . . ?
C4 C3 C2 109.1(7) . . ?
C4 C3 Br3 127.3(6) . . ?
C2 C3 Br3 123.6(5) . . ?
N1 C4 C3 105.6(7) . . ?
N1 C4 C5 122.0(7) . . ?
C3 C4 C5 132.1(8) . . ?
C11 C5 C4 111.0(7) . . ?
C11 C5 C7 110.4(6) . . ?
C4 C5 C7 110.3(6) . . ?
C11 C5 C6 109.5(6) . . ?
C4 C5 C6 105.8(6) . . ?
C7 C5 C6 109.7(7) . . ?
C10 C7 N2 108.3(8) . . ?
C10 C7 C5 130.0(8) . . ?
N2 C7 C5 121.8(8) . . ?
C9 C8 N2 108.6(10) . . ?
C8 C9 C10 108.4(9) . . ?
C7 C10 C9 105.1(8) . . ?
N3 C11 C12 107.2(7) . . ?
N3 C11 C5 121.4(7) . . ?
C12 C11 C5 131.4(7) . . ?
C11 C12 C13 106.8(8) . . ?
C14 C13 C12 108.3(8) . . ?
C13 C14 N3 108.0(9) . . ?
C15 N4 C18 109.0(6) . . ?
C24 N5 C21 109.9(7) . . ?
C25 N6 C28 109.8(7) . . ?
N4 C15 C16 109.0(7) . . ?
N4 C15 Br6 122.0(6) . . ?
C16 C15 Br6 128.7(6) . . ?
C15 C16 C17 106.1(7) . . ?
C15 C16 Br5 126.4(6) . . ?
C17 C16 Br5 127.3(6) . . ?
C18 C17 C16 109.2(7) . . ?
C18 C17 Br4 127.6(6) . . ?
C16 C17 Br4 123.1(6) . . ?
C17 C18 N4 106.7(7) . . ?
C17 C18 C19 133.1(7) . . ?
N4 C18 C19 119.8(6) . . ?
C21 C19 C25 110.5(6) . . ?
C21 C19 C18 110.0(6) . . ?
C25 C19 C18 109.6(6) . . ?
C21 C19 C20 110.1(6) . . ?
C25 C19 C20 109.2(6) . . ?
C18 C19 C20 107.4(6) . . ?
C22 C21 N5 107.3(8) . . ?
C22 C21 C19 131.4(8) . . ?
N5 C21 C19 121.3(7) . . ?
C21 C22 C23 107.4(8) . . ?
C24 C23 C22 106.1(8) . . ?
N5 C24 C23 109.3(7) . . ?
N6 C25 C26 108.0(7) . . ?
N6 C25 C19 122.5(7) . . ?
C26 C25 C19 129.5(7) . . ?
C25 C26 C27 107.8(7) . . ?
C28 C27 C26 106.7(7) . . ?
C27 C28 N6 107.7(7) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N6 H6 Br5  0.88 3.13 3.646(7) 119.3 2_655
 
_diffrn_measured_fraction_theta_max    0.657
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.657
_refine_diff_density_max    0.626
_refine_diff_density_min   -0.835
_refine_diff_density_rms    0.120
