 
data_2005slh0246
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H13 Br2 I N6'
_chemical_formula_weight          600.06
 
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            Orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    10.9213(8)
_cell_length_b                    11.8985(7)
_cell_length_c                    14.8920(11)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1935.2(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2500
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             orange
_exptl_crystal_size_max           0.60
_exptl_crystal_size_mid           0.46
_exptl_crystal_size_min           0.25
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     2.060
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1144
_exptl_absorpt_coefficient_mu     5.801
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.1285
_exptl_absorpt_correction_T_max   0.3249
_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             21807
_diffrn_reflns_av_R_equivalents   0.0343
_diffrn_reflns_av_sigmaI/netI     0.0332
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          3.31
_diffrn_reflns_theta_max          27.49
_reflns_number_total              4405
_reflns_number_gt                 4005
_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     ?
_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)+(0.0631P)²+13.6957P] 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        0.0045(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.12(2)
_refine_ls_number_reflns          4405
_refine_ls_number_parameters      245
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0498
_refine_ls_R_factor_gt            0.0441
_refine_ls_wR_factor_ref          0.1303
_refine_ls_wR_factor_gt           0.1264
_refine_ls_goodness_of_fit_ref    1.102
_refine_ls_restrained_S_all       1.102
_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 0.2953(7) -0.1655(6) -0.0673(5) 0.0159(14) Uani 1 1 d . . .
C2 C 0.2310(6) -0.2737(6) 0.0475(5) 0.0170(13) Uani 1 1 d . . .
C3 C 0.1712(7) -0.3122(6) -0.0934(5) 0.0143(13) Uani 1 1 d . . .
C4 C 0.3633(6) -0.0671(5) -0.1028(4) 0.0153(13) Uani 1 1 d . . .
C5 C 0.3494(7) -0.0260(6) -0.1881(5) 0.0201(15) Uani 1 1 d . . .
H5 H 0.2958 -0.0627 -0.2288 0.024 Uiso 1 1 calc R . .
C6 C 0.4136(7) 0.0695(6) -0.2154(5) 0.0188(14) Uani 1 1 d . . .
H6 H 0.4017 0.0990 -0.2741 0.023 Uiso 1 1 calc R . .
C7 C 0.4947(8) 0.1215(7) -0.1568(5) 0.0235(16) Uani 1 1 d . . .
H7 H 0.5387 0.1870 -0.1738 0.028 Uiso 1 1 calc R . .
C8 C 0.5090(7) 0.0739(6) -0.0726(5) 0.0191(14) Uani 1 1 d . . .
H8 H 0.5657 0.1066 -0.0318 0.023 Uiso 1 1 calc R . .
C9 C 0.2336(7) -0.2996(6) 0.1459(4) 0.0162(14) Uani 1 1 d . . .
C10 C 0.1543(7) -0.3773(7) 0.1746(4) 0.0188(16) Uani 1 1 d . . .
H10 H 0.0994 -0.4144 0.1349 0.023 Uiso 1 1 calc R . .
C11 C 0.1571(8) -0.3995(8) 0.2639(5) 0.0303(19) Uani 1 1 d . . .
H11 H 0.1024 -0.4546 0.2867 0.036 Uiso 1 1 calc R . .
C12 C 0.2347(8) -0.3468(7) 0.3233(5) 0.0255(17) Uani 1 1 d . . .
H12 H 0.2337 -0.3664 0.3851 0.031 Uiso 1 1 calc R . .
C13 C 0.3119(8) -0.2674(7) 0.2929(5) 0.0270(17) Uani 1 1 d . . .
H13 H 0.3653 -0.2294 0.3330 0.032 Uiso 1 1 calc R . .
C14 C 0.1072(6) -0.3857(6) -0.1592(5) 0.0149(14) Uani 1 1 d . . .
C15 C 0.0243(6) -0.4581(5) -0.1259(4) 0.0081(11) Uani 1 1 d . . .
H15 H 0.0071 -0.4606 -0.0634 0.010 Uiso 1 1 calc R . .
C16 C -0.0336(7) -0.5271(7) -0.1837(6) 0.0216(15) Uani 1 1 d . . .
H16 H -0.0926 -0.5783 -0.1610 0.026 Uiso 1 1 calc R . .
C17 C -0.0100(7) -0.5259(7) -0.2748(5) 0.0229(16) Uani 1 1 d . . .
H17 H -0.0511 -0.5767 -0.3137 0.027 Uiso 1 1 calc R . .
C18 C 0.0727(8) -0.4512(6) -0.3082(5) 0.0229(16) Uani 1 1 d . . .
H18 H 0.0879 -0.4476 -0.3710 0.027 Uiso 1 1 calc R . .
N1 N 0.2332(6) -0.2242(5) -0.1277(4) 0.0153(12) Uani 1 1 d . . .
N2 N 0.3015(6) -0.1851(5) 0.0193(4) 0.0150(12) Uani 1 1 d . . .
N3 N 0.1662(6) -0.3381(5) -0.0065(4) 0.0157(12) Uani 1 1 d . . .
N4 N 0.4449(5) -0.0170(5) -0.0467(4) 0.0176(11) Uani 1 1 d . . .
H4 H 0.4561 -0.0445 0.0075 0.021 Uiso 0.33 1 calc PR . .
N5 N 0.3124(7) -0.2421(7) 0.2032(5) 0.0340(17) Uani 1 1 d . . .
H5A H 0.3619 -0.1901 0.1821 0.041 Uiso 0.33 1 calc PR . .
N6 N 0.1348(7) -0.3802(6) -0.2495(5) 0.0307(16) Uani 1 1 d . . .
H6A H 0.1903 -0.3329 -0.2695 0.037 Uiso 0.33 1 calc PR . .
Br2 Br -0.02334(7) -0.08901(8) 0.03991(7) 0.0351(2) Uani 1 1 d . . .
Br1 Br 0.29145(9) 0.24996(8) 0.04814(7) 0.0422(2) Uani 1 1 d . . .
I1 I 0.12956(4) 0.08322(4) 0.04421(3) 0.01854(15) Uani 1 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
C1 N2 1.312(9) . ?
C1 N1 1.326(9) . ?
C1 C4 1.483(9) . ?
C2 N3 1.316(9) . ?
C2 N2 1.372(9) . ?
C2 C9 1.497(10) . ?
C3 N3 1.331(9) . ?
C3 N1 1.348(9) . ?
C3 C14 1.488(10) . ?
C4 N4 1.359(9) . ?
C4 C5 1.369(10) . ?
C5 C6 1.396(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(10) . ?
C7 H7 0.9500 . ?
C8 N4 1.344(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.337(11) . ?
C9 N5 1.393(10) . ?
C10 C11 1.357(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.346(12) . ?
C12 H12 0.9500 . ?
C13 N5 1.368(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.344(9) . ?
C14 N6 1.379(10) . ?
C15 C16 1.347(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.361(11) . ?
C17 H17 0.9500 . ?
C18 N6 1.392(11) . ?
C18 H18 0.9500 . ?
N4 H4 0.8800 . ?
N5 H5A 0.8800 . ?
N6 H6A 0.8800 . ?
Br2 I1 2.6442(10) . ?
Br1 I1 2.6582(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
N2 C1 N1 126.8(7) . . ?
N2 C1 C4 117.7(6) . . ?
N1 C1 C4 115.5(6) . . ?
N3 C2 N2 124.2(7) . . ?
N3 C2 C9 119.2(6) . . ?
N2 C2 C9 116.6(6) . . ?
N3 C3 N1 124.7(7) . . ?
N3 C3 C14 119.0(7) . . ?
N1 C3 C14 116.3(6) . . ?
N4 C4 C5 119.1(6) . . ?
N4 C4 C1 117.1(6) . . ?
C5 C4 C1 123.8(6) . . ?
C4 C5 C6 120.4(7) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 119.9(7) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 117.3(7) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
N4 C8 C7 122.0(7) . . ?
N4 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C10 C9 N5 123.0(7) . . ?
C10 C9 C2 116.3(6) . . ?
N5 C9 C2 120.7(7) . . ?
C9 C10 C11 115.7(7) . . ?
C9 C10 H10 122.1 . . ?
C11 C10 H10 122.1 . . ?
C10 C11 C12 123.7(8) . . ?
C10 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C13 C12 C11 119.3(7) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 N5 119.0(8) . . ?
C12 C13 H13 120.5 . . ?
N5 C13 H13 120.5 . . ?
C15 C14 N6 122.5(6) . . ?
C15 C14 C3 116.7(6) . . ?
N6 C14 C3 120.8(7) . . ?
C14 C15 C16 118.1(6) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C15 C16 C17 122.3(7) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C18 C17 C16 119.3(7) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 N6 119.3(7) . . ?
C17 C18 H18 120.4 . . ?
N6 C18 H18 120.4 . . ?
C1 N1 C3 114.1(6) . . ?
C1 N2 C2 114.2(6) . . ?
C2 N3 C3 115.9(7) . . ?
C8 N4 C4 121.2(6) . . ?
C8 N4 H4 119.4 . . ?
C4 N4 H4 119.4 . . ?
C13 N5 C9 119.2(8) . . ?
C13 N5 H5A 120.4 . . ?
C9 N5 H5A 120.4 . . ?
C14 N6 C18 118.5(7) . . ?
C14 N6 H6A 120.7 . . ?
C18 N6 H6A 120.7 . . ?
Br2 I1 Br1 177.47(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    1.368
_refine_diff_density_min   -1.934
_refine_diff_density_rms    0.202
