data_2009src0924

#Dr. P. J. Holliman
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H16 I N'
_chemical_formula_weight          301.16
 
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'
 '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                    6.95290(10)
_cell_length_b                    11.4620(3)
_cell_length_c                    15.7644(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1256.33(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     1635
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Blade
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.22
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.592
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              592
_exptl_absorpt_coefficient_mu     2.514
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6077
_exptl_absorpt_correction_T_max   0.8638
_exptl_absorpt_process_details       'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details
;
SADABS was used to perform the Absorption correction
Estimated minimum and maximum transmission: 0.6078 0.7456
The given Tmin and Tmax were generated using the SHELX SIZE command
;

_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 Roper 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             9836
_diffrn_reflns_av_R_equivalents   0.0396
_diffrn_reflns_av_sigmaI/netI     0.0462
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.14
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2843
_reflns_number_gt                 2723
_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, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX (Farrugia, 1999)'
 
_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)+(0.0079P)²+0.6432P] 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        0.0025(4)
_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    0.01(3)
_refine_ls_number_reflns          2843
_refine_ls_number_parameters      132
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0282
_refine_ls_R_factor_gt            0.0261
_refine_ls_wR_factor_ref          0.0520
_refine_ls_wR_factor_gt           0.0509
_refine_ls_goodness_of_fit_ref    1.074
_refine_ls_restrained_S_all       1.074
_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 0.0836(5) 0.5685(3) 0.1785(2) 0.0155(7) Uani 1 1 d . . .
C2 C 0.1518(5) 0.5795(3) 0.0881(2) 0.0160(7) Uani 1 1 d . . .
C3 C 0.0182(5) 0.4965(3) 0.0431(2) 0.0157(7) Uani 1 1 d . . .
C4 C -0.1036(5) 0.4456(3) 0.1021(2) 0.0148(7) Uani 1 1 d . . .
C5 C -0.2375(5) 0.3608(3) 0.0832(2) 0.0180(7) Uani 1 1 d . . .
H5 H -0.3189 0.3278 0.1253 0.022 Uiso 1 1 calc R . .
C6 C -0.2461(5) 0.3262(3) -0.0019(2) 0.0239(9) Uani 1 1 d . . .
H6 H -0.3343 0.2671 -0.0183 0.029 Uiso 1 1 calc R . .
C7 C -0.1283(5) 0.3767(3) -0.0626(2) 0.0246(9) Uani 1 1 d . . .
H7 H -0.1379 0.3520 -0.1200 0.029 Uiso 1 1 calc R . .
C8 C 0.0038(5) 0.4630(3) -0.0411(2) 0.0219(8) Uani 1 1 d . . .
H8 H 0.0825 0.4981 -0.0832 0.026 Uiso 1 1 calc R . .
C9 C -0.1619(6) 0.4649(3) 0.2610(2) 0.0205(8) Uani 1 1 d . . .
H9A H -0.0911 0.4040 0.2915 0.031 Uiso 1 1 calc R . .
H9B H -0.2905 0.4362 0.2464 0.031 Uiso 1 1 calc R . .
H9C H -0.1735 0.5341 0.2972 0.031 Uiso 1 1 calc R . .
C10 C 0.1647(6) 0.6304(3) 0.2518(2) 0.0192(7) Uani 1 1 d . . .
H10A H 0.0669 0.6819 0.2762 0.029 Uiso 1 1 calc R . .
H10B H 0.2755 0.6769 0.2335 0.029 Uiso 1 1 calc R . .
H10C H 0.2061 0.5736 0.2946 0.029 Uiso 1 1 calc R . .
C11 C 0.3634(5) 0.5402(3) 0.0790(2) 0.0232(8) Uani 1 1 d . . .
H11A H 0.3766 0.4598 0.0993 0.035 Uiso 1 1 calc R . .
H11B H 0.4462 0.5916 0.1126 0.035 Uiso 1 1 calc R . .
H11C H 0.4015 0.5442 0.0192 0.035 Uiso 1 1 calc R . .
C12 C 0.1294(5) 0.7076(3) 0.0576(2) 0.0232(8) Uani 1 1 d . . .
H12A H 0.1494 0.7113 -0.0039 0.035 Uiso 1 1 calc R . .
H12B H 0.2249 0.7567 0.0862 0.035 Uiso 1 1 calc R . .
H12C H -0.0001 0.7356 0.0713 0.035 Uiso 1 1 calc R . .
N1 N -0.0588(4) 0.4953(2) 0.18375(17) 0.0140(6) Uani 1 1 d . . .
I1 I 0.67406(3) 0.799047(17) 0.217956(14) 0.01805(8) Uani 1 1 d . . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.0131(17) 0.0128(16) 0.0206(19) 0.0036(14) -0.0010(13) 0.0060(12)
C2 0.0162(18) 0.0158(15) 0.0160(17) 0.0004(13) 0.0017(15) 0.0009(14)
C3 0.0146(18) 0.0165(16) 0.0162(18) 0.0009(14) -0.0007(14) 0.0046(14)
C4 0.0145(17) 0.0150(15) 0.0148(18) 0.0015(13) -0.0008(13) 0.0043(12)
C5 0.0141(18) 0.0159(16) 0.024(2) 0.0021(15) -0.0040(14) 0.0005(12)
C6 0.024(2) 0.021(2) 0.027(2) -0.0031(16) -0.0111(16) -0.0015(14)
C7 0.031(2) 0.0227(18) 0.0201(19) -0.0051(15) -0.0085(16) 0.0041(15)
C8 0.029(2) 0.0205(18) 0.0165(19) -0.0003(14) 0.0028(17) 0.0051(15)
C9 0.0210(19) 0.0212(16) 0.0192(19) 0.0003(13) 0.0041(16) 0.0019(16)
C10 0.0198(19) 0.0171(15) 0.0208(17) -0.0020(13) -0.0007(15) 0.0010(15)
C11 0.021(2) 0.0209(17) 0.028(2) -0.0008(15) 0.0028(16) -0.0001(15)
C12 0.030(2) 0.0156(16) 0.0245(19) 0.0043(16) 0.0060(15) -0.0018(16)
N1 0.0136(15) 0.0134(13) 0.0152(14) 0.0007(11) -0.0004(10) 0.0030(11)
I1 0.01660(12) 0.01745(11) 0.02009(13) 0.00199(9) 0.00018(9) -0.00017(9)
 
_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 N1 1.300(4) . ?
C1 C10 1.468(5) . ?
C1 C2 1.508(5) . ?
C2 C3 1.508(4) . ?
C2 C11 1.545(5) . ?
C2 C12 1.552(4) . ?
C3 C8 1.385(5) . ?
C3 C4 1.387(5) . ?
C4 C5 1.379(5) . ?
C4 N1 1.441(4) . ?
C5 C6 1.400(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N1 1.456(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
 
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
N1 C1 C10 123.7(3) . . ?
N1 C1 C2 110.7(3) . . ?
C10 C1 C2 125.6(3) . . ?
C3 C2 C1 101.4(3) . . ?
C3 C2 C11 111.0(3) . . ?
C1 C2 C11 111.3(3) . . ?
C3 C2 C12 112.9(3) . . ?
C1 C2 C12 109.9(3) . . ?
C11 C2 C12 110.0(3) . . ?
C8 C3 C4 118.8(3) . . ?
C8 C3 C2 132.1(3) . . ?
C4 C3 C2 109.0(3) . . ?
C5 C4 C3 124.3(3) . . ?
C5 C4 N1 128.1(3) . . ?
C3 C4 N1 107.5(3) . . ?
C4 C5 C6 115.8(3) . . ?
C4 C5 H5 122.1 . . ?
C6 C5 H5 122.1 . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 121.2(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 118.6(3) . . ?
C3 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 C4 111.3(3) . . ?
C1 N1 C9 125.6(3) . . ?
C4 N1 C9 123.1(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.827
_refine_diff_density_min   -0.503
_refine_diff_density_rms    0.094
