 
data_2006cgl0741
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H13 Br7 N2'
_chemical_formula_weight          840.69
 
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            Triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.0558(3)
_cell_length_b                    13.6319(3)
_cell_length_c                    14.1191(5)
_cell_angle_alpha                 106.205(2)
_cell_angle_beta                  95.292(2)
_cell_angle_gamma                 104.352(2)
_cell_volume                      1244.22(7)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     5401
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             orange
_exptl_crystal_size_max           0.34
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.16
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     2.244
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              784
_exptl_absorpt_coefficient_mu     11.297
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.1139
_exptl_absorpt_correction_T_max   0.2651
_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             22322
_diffrn_reflns_av_R_equivalents   0.0561
_diffrn_reflns_av_sigmaI/netI     0.0567
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.97
_diffrn_reflns_theta_max          27.50
_reflns_number_total              5676
_reflns_number_gt                 4147
_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)+(0.0313P)²+3.8854P] 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        0.0019(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5676
_refine_ls_number_parameters      263
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0710
_refine_ls_R_factor_gt            0.0402
_refine_ls_wR_factor_ref          0.0895
_refine_ls_wR_factor_gt           0.0795
_refine_ls_goodness_of_fit_ref    1.020
_refine_ls_restrained_S_all       1.020
_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 0.5477(7) 0.0607(4) -0.2365(4) 0.0244(11) Uani 1 1 d . . .
C2 C 0.5113(7) -0.0452(4) -0.2419(4) 0.0238(11) Uani 1 1 d . . .
H2 H 0.4621 -0.0679 -0.1888 0.029 Uiso 1 1 calc R . .
C3 C 0.6183(7) -0.0883(4) -0.3952(4) 0.0266(12) Uani 1 1 d . . .
H3 H 0.6382 -0.1414 -0.4502 0.032 Uiso 1 1 calc R . .
C4 C 0.6666(8) 0.0163(4) -0.3939(4) 0.0290(12) Uani 1 1 d . . .
H4 H 0.7233 0.0369 -0.4464 0.035 Uiso 1 1 calc R . .
C5 C 0.6298(8) 0.0912(4) -0.3132(4) 0.0299(12) Uani 1 1 d . . .
H5 H 0.6613 0.1639 -0.3107 0.036 Uiso 1 1 calc R . .
C6 C 0.5085(8) 0.1364(4) -0.1470(4) 0.0298(12) Uani 1 1 d . . .
C7 C 0.3935(8) 0.1986(4) -0.1468(4) 0.0294(12) Uani 1 1 d . . .
C8 C 0.3595(8) 0.2769(4) -0.0580(4) 0.0273(12) Uani 1 1 d . . .
C9 C 0.1676(8) 0.2681(4) -0.0378(4) 0.0329(13) Uani 1 1 d . . .
H9 H 0.0597 0.2109 -0.0796 0.039 Uiso 1 1 calc R . .
C10 C 0.1337(8) 0.3422(4) 0.0428(4) 0.0273(12) Uani 1 1 d . . .
H10 H 0.0025 0.3357 0.0563 0.033 Uiso 1 1 calc R . .
C11 C 0.2908(7) 0.4268(4) 0.1046(4) 0.0220(10) Uani 1 1 d . . .
C12 C 0.4833(8) 0.4352(4) 0.0857(4) 0.0250(11) Uani 1 1 d . . .
H12 H 0.5913 0.4921 0.1280 0.030 Uiso 1 1 calc R . .
C13 C 0.5169(8) 0.3601(4) 0.0046(4) 0.0278(12) Uani 1 1 d . . .
H13 H 0.6484 0.3656 -0.0082 0.033 Uiso 1 1 calc R . .
C14 C 0.2560(7) 0.5083(4) 0.1906(4) 0.0231(11) Uani 1 1 d . . .
C15 C 0.3531(8) 0.5374(4) 0.2839(4) 0.0242(11) Uani 1 1 d . . .
C16 C 0.4934(8) 0.4834(4) 0.3167(4) 0.0248(11) Uani 1 1 d . . .
C17 C 0.4316(8) 0.3739(4) 0.3012(4) 0.0256(11) Uani 1 1 d . . .
H17 H 0.2979 0.3352 0.2712 0.031 Uiso 1 1 calc R . .
C18 C 0.7428(8) 0.3755(4) 0.3685(4) 0.0332(13) Uani 1 1 d . . .
H18 H 0.8308 0.3378 0.3851 0.040 Uiso 1 1 calc R . .
C19 C 0.8137(9) 0.4838(5) 0.3880(5) 0.0437(16) Uani 1 1 d . . .
H19 H 0.9479 0.5207 0.4185 0.052 Uiso 1 1 calc R . .
C20 C 0.6865(8) 0.5380(4) 0.3625(4) 0.0349(13) Uani 1 1 d . . .
H20 H 0.7321 0.6131 0.3765 0.042 Uiso 1 1 calc R . .
N1 N 0.5440(6) -0.1155(3) -0.3200(3) 0.0224(9) Uani 1 1 d . . .
H1N H 0.5154 -0.1828 -0.3223 0.027 Uiso 1 1 d R . .
N2 N 0.5542(7) 0.3212(3) 0.3271(3) 0.0293(10) Uani 1 1 d . . .
Br1 Br 0.64093(8) 0.13354(4) -0.02404(4) 0.02627(13) Uani 1 1 d . . .
Br2 Br 0.24664(8) 0.19033(4) -0.27146(4) 0.03023(14) Uani 1 1 d . . .
Br3 Br 0.06715(8) 0.57628(4) 0.15611(4) 0.03326(15) Uani 1 1 d . . .
Br4 Br 0.31805(9) 0.65055(4) 0.38752(4) 0.03555(16) Uani 1 1 d . . .
Br5 Br 0.96615(8) 0.19698(4) 0.49223(4) 0.03206(15) Uani 1 1 d . . .
Br6 Br 0.98281(7) 0.13631(4) 0.29953(4) 0.02819(14) Uani 1 1 d . . .
Br7 Br 1.00466(11) 0.07392(6) 0.12145(5) 0.0558(2) 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 C2 1.380(7) . ?
C1 C5 1.389(7) . ?
C1 C6 1.489(7) . ?
C2 N1 1.325(6) . ?
C2 H2 0.9500 . ?
C3 N1 1.328(7) . ?
C3 C4 1.376(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(7) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.311(7) . ?
C6 Br1 1.909(6) . ?
C7 C8 1.485(7) . ?
C7 Br2 1.918(5) . ?
C8 C13 1.392(7) . ?
C8 C9 1.393(7) . ?
C9 C10 1.378(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(7) . ?
C11 C14 1.485(7) . ?
C12 C13 1.390(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.331(7) . ?
C14 Br3 1.902(5) . ?
C15 C16 1.484(7) . ?
C15 Br4 1.891(5) . ?
C16 C20 1.376(7) . ?
C16 C17 1.395(7) . ?
C17 N2 1.339(6) . ?
C17 H17 0.9500 . ?
C18 N2 1.337(7) . ?
C18 C19 1.375(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(8) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
N1 H1N 0.8800 . ?
Br5 Br6 2.6367(8) . ?
Br6 Br7 2.4518(9) . ?
 
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 C5 117.4(5) . . ?
C2 C1 C6 118.7(5) . . ?
C5 C1 C6 123.8(5) . . ?
N1 C2 C1 120.9(5) . . ?
N1 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
N1 C3 C4 120.3(5) . . ?
N1 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 118.0(5) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C1 C5 C4 120.8(5) . . ?
C1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C1 126.6(5) . . ?
C7 C6 Br1 120.6(5) . . ?
C1 C6 Br1 112.8(4) . . ?
C6 C7 C8 126.8(5) . . ?
C6 C7 Br2 119.1(4) . . ?
C8 C7 Br2 114.2(4) . . ?
C13 C8 C9 119.4(5) . . ?
C13 C8 C7 120.8(5) . . ?
C9 C8 C7 119.8(5) . . ?
C10 C9 C8 120.2(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.4(5) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.7(5) . . ?
C12 C11 C14 119.3(4) . . ?
C10 C11 C14 121.0(4) . . ?
C13 C12 C11 119.7(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C8 120.5(5) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C15 C14 C11 124.5(4) . . ?
C15 C14 Br3 121.1(4) . . ?
C11 C14 Br3 114.4(4) . . ?
C14 C15 C16 123.6(4) . . ?
C14 C15 Br4 122.2(4) . . ?
C16 C15 Br4 114.2(4) . . ?
C20 C16 C17 117.7(5) . . ?
C20 C16 C15 122.1(4) . . ?
C17 C16 C15 120.1(5) . . ?
N2 C17 C16 122.3(5) . . ?
N2 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
N2 C18 C19 122.3(5) . . ?
N2 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C20 118.8(5) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C16 C20 C19 120.1(5) . . ?
C16 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C2 N1 C3 122.6(4) . . ?
C2 N1 H1N 118.7 . . ?
C3 N1 H1N 118.7 . . ?
C18 N2 C17 118.8(4) . . ?
Br7 Br6 Br5 177.52(3) . . ?
 
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
N1 H1N N2  0.88 1.81 2.689(6) 177.6 2_655
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    1.353
_refine_diff_density_min   -1.247
_refine_diff_density_rms    0.151
