 
data_2005slh0248
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H15 Br8 I5 N6'
_chemical_formula_weight          1589.14
 
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'
 'I'  'I'  -0.4742   1.8119
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.156(2)
_cell_length_b                    14.103(4)
_cell_length_c                    16.380(6)
_cell_angle_alpha                 90.94(2)
_cell_angle_beta                  99.31(2)
_cell_angle_gamma                 100.91(2)
_cell_volume                      1823.5(10)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     8008
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut needle'
_exptl_crystal_colour             orange
_exptl_crystal_size_max           0.46
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     2.894
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1420
_exptl_absorpt_coefficient_mu     13.050
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.0654
_exptl_absorpt_correction_T_max   0.7803
_exptl_absorpt_process_details    
'SADABS V2.10 (Sheldrick, G.M., 2003)' 
 
_exptl_special_details
;
 ?
;
 
_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   graphite
_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             36779
_diffrn_reflns_av_R_equivalents   0.0851
_diffrn_reflns_av_sigmaI/netI     0.0919
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.06
_diffrn_reflns_theta_max          27.50
_reflns_number_total              8316
_reflns_number_gt                 4961
_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, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_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)+(0.0477P)²+10.5782P] 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      SHELXL
_refine_ls_extinction_coef        0.00031(8)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          8316
_refine_ls_number_parameters      338
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1154
_refine_ls_R_factor_gt            0.0517
_refine_ls_wR_factor_ref          0.1239
_refine_ls_wR_factor_gt           0.1027
_refine_ls_goodness_of_fit_ref    1.015
_refine_ls_restrained_S_all       1.015
_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
C1 C 1.0848(11) 0.1998(7) 0.3586(6) 0.027(2) Uani 1 1 d . . .
C2 C 1.0115(11) 0.0594(7) 0.2842(6) 0.024(2) Uani 1 1 d . . .
C3 C 0.9202(11) 0.1918(7) 0.2324(6) 0.023(2) Uani 1 1 d . . .
C4 C 1.1687(11) 0.2544(7) 0.4359(6) 0.025(2) Uani 1 1 d . . .
C5 C 1.2436(13) 0.2081(9) 0.5015(6) 0.037(3) Uani 1 1 d . . .
H5 H 1.2434 0.1407 0.4989 0.044 Uiso 1 1 calc R . .
C6 C 1.3214(15) 0.2689(14) 0.5734(8) 0.070(5) Uani 1 1 d . . .
H6 H 1.3817 0.2427 0.6194 0.084 Uiso 1 1 calc R . .
C7 C 1.3098(16) 0.3665(14) 0.5769(10) 0.072(5) Uani 1 1 d . . .
H7 H 1.3591 0.4059 0.6256 0.086 Uiso 1 1 calc R . .
C8 C 1.2315(19) 0.4031(11) 0.5135(10) 0.070(4) Uani 1 1 d . . .
H8 H 1.2235 0.4694 0.5163 0.084 Uiso 1 1 calc R . .
C9 C 1.0026(11) -0.0464(7) 0.2780(6) 0.022(2) Uani 1 1 d . . .
C10 C 1.0779(12) -0.0955(8) 0.3377(7) 0.032(2) Uani 1 1 d . . .
H10 H 1.1460 -0.0617 0.3858 0.038 Uiso 1 1 calc R . .
C11 C 1.0570(14) -0.1951(9) 0.3296(8) 0.048(3) Uani 1 1 d . . .
H11 H 1.1110 -0.2299 0.3716 0.058 Uiso 1 1 calc R . .
C12 C 0.9547(15) -0.2441(9) 0.2582(9) 0.051(3) Uani 1 1 d . . .
H12 H 0.9388 -0.3124 0.2512 0.062 Uiso 1 1 calc R . .
C13 C 0.8798(15) -0.1927(8) 0.2001(8) 0.046(3) Uani 1 1 d . . .
H13 H 0.8089 -0.2248 0.1520 0.055 Uiso 1 1 calc R . .
C14 C 0.8291(11) 0.2385(7) 0.1667(6) 0.023(2) Uani 1 1 d . . .
C15 C 0.7563(11) 0.1900(7) 0.0920(6) 0.029(2) Uani 1 1 d . . .
H15 H 0.7594 0.1238 0.0827 0.035 Uiso 1 1 calc R . .
C16 C 0.6756(13) 0.2435(13) 0.0287(7) 0.065(5) Uani 1 1 d . . .
H16 H 0.6274 0.2137 -0.0244 0.077 Uiso 1 1 calc R . .
C17 C 0.6693(16) 0.3403(14) 0.0467(12) 0.072(5) Uani 1 1 d . . .
H17 H 0.6161 0.3765 0.0056 0.087 Uiso 1 1 calc R . .
C18 C 0.7359(16) 0.3805(11) 0.1193(11) 0.064(4) Uani 1 1 d . . .
H18 H 0.7268 0.4453 0.1308 0.077 Uiso 1 1 calc R . .
N1 N 0.9975(9) 0.2466(5) 0.3007(5) 0.0230(17) Uani 1 1 d . . .
N2 N 1.0995(9) 0.1072(6) 0.3519(5) 0.0241(18) Uani 1 1 d . . .
N3 N 0.9180(9) 0.0973(5) 0.2209(5) 0.0248(18) Uani 1 1 d . . .
N4 N 1.1612(11) 0.3487(7) 0.4436(6) 0.040(2) Uani 1 1 d . . .
H4 H 1.1086 0.3757 0.4017 0.048 Uiso 1 1 d R . .
N5 N 0.9052(10) -0.0947(6) 0.2100(6) 0.035(2) Uani 1 1 d . . .
H5A H 0.8568 -0.0620 0.1710 0.042 Uiso 1 1 d R . .
N6 N 0.8165(11) 0.3344(6) 0.1783(6) 0.042(2) Uani 1 1 d . . .
H6A H 0.8629 0.3654 0.2260 0.050 Uiso 1 1 d R . .
Br1 Br 0.55535(14) 0.16548(8) 0.77934(7) 0.0405(3) Uani 1 1 d . . .
I1 I 0.58458(8) -0.01552(6) 0.79126(4) 0.0403(2) Uani 1 1 d . . .
Br8 Br 0.78376(13) 0.03883(9) 0.43394(7) 0.0401(3) Uani 1 1 d . . .
I6 I 0.5000 0.0000 0.5000 0.0301(2) Uani 1 2 d S . .
Br2 Br 0.36057(14) 0.22008(10) 0.19131(7) 0.0469(3) Uani 1 1 d . . .
Br3 Br 0.73876(15) 0.33317(10) 0.49485(8) 0.0502(3) Uani 1 1 d . . .
I2 I 0.56138(8) 0.28348(5) 0.34970(5) 0.0383(2) Uani 1 1 d . . .
Br5 Br -0.01684(13) 0.51149(8) 0.33033(7) 0.0374(3) Uani 1 1 d . . .
Br6 Br 0.53488(14) 0.58555(10) 0.17843(8) 0.0506(3) Uani 1 1 d . . .
I4 I 0.26714(8) 0.54617(5) 0.25368(4) 0.03465(19) Uani 1 1 d . . .
Br4 Br 0.99359(14) 0.60835(8) 0.08023(7) 0.0401(3) Uani 1 1 d . . .
I3 I 0.81309(9) 0.67515(6) -0.04475(5) 0.0441(2) Uani 1 1 d . . .
Br7 Br 0.68443(13) 0.93658(8) 0.03119(7) 0.0377(3) Uani 1 1 d . . .
I5 I 1.0000 1.0000 0.0000 0.0322(2) Uani 1 2 d S . .
 
 
_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 N2 1.338(12) . ?
C1 N1 1.350(12) . ?
C1 C4 1.467(13) . ?
C2 N2 1.317(12) . ?
C2 N3 1.363(12) . ?
C2 C9 1.481(13) . ?
C3 N3 1.339(12) . ?
C3 N1 1.343(12) . ?
C3 C14 1.448(13) . ?
C4 N4 1.347(13) . ?
C4 C5 1.385(14) . ?
C5 C6 1.430(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.40(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.30(2) . ?
C7 H7 0.9500 . ?
C8 N4 1.350(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.343(14) . ?
C9 N5 1.349(12) . ?
C10 C11 1.384(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.408(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.344(17) . ?
C12 H12 0.9500 . ?
C13 N5 1.361(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(13) . ?
C14 N6 1.388(12) . ?
C15 C16 1.438(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.40(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.30(2) . ?
C17 H17 0.9500 . ?
C18 N6 1.329(16) . ?
C18 H18 0.9500 . ?
N4 H4 0.8800 . ?
N5 H5A 0.8800 . ?
N6 H6A 0.8800 . ?
Br1 I1 2.6158(16) . ?
Br8 I6 2.6789(12) . ?
I6 Br8 2.6789(12) 2_656 ?
Br2 I2 2.8649(17) . ?
Br3 I2 2.5856(17) . ?
Br5 I4 2.7772(15) . ?
Br6 I4 2.6515(15) . ?
Br4 I3 2.6190(16) . ?
Br7 I5 2.6934(12) . ?
I5 Br7 2.6934(12) 2_775 ?
 
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
N2 C1 N1 125.5(9) . . ?
N2 C1 C4 117.1(9) . . ?
N1 C1 C4 117.4(8) . . ?
N2 C2 N3 126.0(8) . . ?
N2 C2 C9 117.6(8) . . ?
N3 C2 C9 116.3(8) . . ?
N3 C3 N1 125.4(9) . . ?
N3 C3 C14 117.4(8) . . ?
N1 C3 C14 117.1(8) . . ?
N4 C4 C5 120.8(9) . . ?
N4 C4 C1 118.7(9) . . ?
C5 C4 C1 120.3(9) . . ?
C4 C5 C6 115.2(11) . . ?
C4 C5 H5 122.4 . . ?
C6 C5 H5 122.4 . . ?
C7 C6 C5 120.8(12) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 119.8(13) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 N4 121.1(15) . . ?
C7 C8 H8 119.4 . . ?
N4 C8 H8 119.4 . . ?
C10 C9 N5 119.6(9) . . ?
C10 C9 C2 123.6(9) . . ?
N5 C9 C2 116.8(8) . . ?
C9 C10 C11 120.4(10) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.0(11) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 118.9(11) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 N5 120.2(11) . . ?
C12 C13 H13 119.9 . . ?
N5 C13 H13 119.9 . . ?
C15 C14 N6 119.1(9) . . ?
C15 C14 C3 121.3(9) . . ?
N6 C14 C3 119.6(8) . . ?
C14 C15 C16 117.5(11) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
C17 C16 C15 119.0(12) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C18 C17 C16 120.1(13) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 N6 122.5(14) . . ?
C17 C18 H18 118.7 . . ?
N6 C18 H18 118.7 . . ?
C3 N1 C1 114.3(8) . . ?
C2 N2 C1 114.7(8) . . ?
C3 N3 C2 113.9(8) . . ?
C4 N4 C8 122.2(12) . . ?
C4 N4 H4 118.9 . . ?
C8 N4 H4 118.9 . . ?
C9 N5 C13 121.8(9) . . ?
C9 N5 H5A 119.1 . . ?
C13 N5 H5A 119.1 . . ?
C18 N6 C14 121.6(11) . . ?
C18 N6 H6A 119.2 . . ?
C14 N6 H6A 119.2 . . ?
Br8 I6 Br8 180.0 2_656 . ?
Br3 I2 Br2 177.49(5) . . ?
Br6 I4 Br5 177.79(5) . . ?
Br7 I5 Br7 180.0 2_775 . ?
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    2.021
_refine_diff_density_min   -2.051
_refine_diff_density_rms    0.242
