data_pna21
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          
 'C11 H14 N S, I'
_chemical_formula_sum
 'C11 H14 I N S'
_chemical_formula_weight          319.19
 
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'
 'S'  'S'   0.1246   0.1234
 '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    Pna2(1)
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 '-x+1/2, y+1/2, z+1/2'
 'x+1/2, -y+1/2, z'
 
_cell_length_a                    17.471(3)
_cell_length_b                    13.112(2)
_cell_length_c                    5.2955(9)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1213.1(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     5645
_cell_measurement_theta_min       2.33
_cell_measurement_theta_max       28.26
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.30
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.748
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              624
_exptl_absorpt_coefficient_mu     2.775
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   0.343
_exptl_absorpt_correction_T_max   0.574
_exptl_absorpt_process_details    'SADABS'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       173(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   'CCD area detector'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             12793
_diffrn_reflns_av_R_equivalents   0.0868
_diffrn_reflns_av_sigmaI/netI     0.0642
_diffrn_reflns_limit_h_min        -22
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -6
_diffrn_reflns_limit_l_max        6
_diffrn_reflns_theta_min          1.94
_diffrn_reflns_theta_max          28.09
_reflns_number_total              2771
_reflns_number_gt                 2186
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Bruker SMART'
_computing_cell_refinement        'Bruker SMART'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'Bruker SHELXTL'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
 
_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)+(0.0642P)²+0.5090P] 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      none
_refine_ls_extinction_coef        ?
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.03(6)
_refine_ls_number_reflns          2771
_refine_ls_number_parameters      127
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0782
_refine_ls_R_factor_gt            0.0526
_refine_ls_wR_factor_ref          0.1402
_refine_ls_wR_factor_gt           0.1198
_refine_ls_goodness_of_fit_ref    1.226
_refine_ls_restrained_S_all       1.226
_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
C1 C 0.1324(5) 0.9539(6) 0.7800(18) 0.022(2) Uani 1 1 d . . .
H1 H 0.1495 1.0027 0.6656 0.026 Uiso 1 1 calc R . .
C2 C 0.0617(5) 0.8424(7) 1.0609(18) 0.0224(19) Uani 1 1 d . . .
C3 C 0.0125(5) 0.7866(7) 1.217(3) 0.030(2) Uani 1 1 d . . .
H3 H -0.0403 0.7897 1.1968 0.036 Uiso 1 1 calc R . .
C4 C 0.0456(6) 0.7268(8) 1.4007(19) 0.031(2) Uani 1 1 d . . .
H4 H 0.0139 0.6895 1.5075 0.037 Uiso 1 1 calc R . .
C5 C 0.1241(6) 0.7199(7) 1.4331(19) 0.028(2) Uani 1 1 d . . .
H5 H 0.1442 0.6791 1.5604 0.033 Uiso 1 1 calc R . .
C6 C 0.1731(5) 0.7746(6) 1.273(2) 0.025(3) Uani 1 1 d . . .
H6 H 0.2260 0.7691 1.2892 0.030 Uiso 1 1 calc R . .
C7 C 0.1413(5) 0.8357(7) 1.0954(18) 0.0203(18) Uani 1 1 d . . .
C21 C 0.2627(5) 0.9155(7) 0.9316(17) 0.0222(19) Uani 1 1 d . . .
H21A H 0.2868 0.8497 0.9584 0.027 Uiso 1 1 calc R . .
H21B H 0.2755 0.9587 1.0740 0.027 Uiso 1 1 calc R . .
C22 C 0.2947(5) 0.9629(7) 0.6912(15) 0.025(2) Uani 1 1 d . . .
H22A H 0.2787 0.9233 0.5458 0.030 Uiso 1 1 calc R . .
H22B H 0.2752 1.0317 0.6719 0.030 Uiso 1 1 calc R . .
C23 C 0.3816(5) 0.9652(7) 0.705(2) 0.027(2) Uani 1 1 d . . .
H23A H 0.3971 1.0044 0.8520 0.033 Uiso 1 1 calc R . .
H23B H 0.4006 0.8962 0.7259 0.033 Uiso 1 1 calc R . .
C24 C 0.4163(6) 1.0116(10) 0.472(2) 0.044(3) Uani 1 1 d . . .
H24A H 0.4710 1.0126 0.4884 0.066 Uiso 1 1 calc R . .
H24B H 0.3977 1.0800 0.4518 0.066 Uiso 1 1 calc R . .
H24C H 0.4023 0.9717 0.3273 0.066 Uiso 1 1 calc R . .
N N 0.1793(4) 0.9016(6) 0.9233(14) 0.0217(17) Uani 1 1 d . . .
S S 0.03859(13) 0.92624(19) 0.8182(4) 0.0255(5) Uani 1 1 d . . .
I I 0.16275(3) 0.14917(4) 0.23848(18) 0.02741(18) 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 0.020(4) 0.028(4) 0.018(6) 0.006(4) -0.002(4) 0.002(4)
C2 0.015(4) 0.023(5) 0.030(5) -0.007(4) 0.001(4) 0.003(4)
C3 0.016(4) 0.034(4) 0.041(6) -0.002(6) -0.010(5) -0.003(3)
C4 0.030(5) 0.029(5) 0.035(6) 0.000(4) 0.005(4) -0.012(5)
C5 0.030(6) 0.021(5) 0.033(5) 0.002(4) 0.001(4) 0.003(4)
C6 0.024(4) 0.019(4) 0.031(8) -0.005(5) 0.003(5) 0.002(3)
C7 0.018(4) 0.020(4) 0.023(5) -0.003(4) -0.002(4) 0.001(4)
C21 0.018(5) 0.025(5) 0.024(5) 0.002(4) -0.003(4) -0.002(4)
C22 0.033(5) 0.032(5) 0.009(6) 0.001(4) 0.001(4) -0.005(4)
C23 0.022(4) 0.032(4) 0.027(7) 0.000(5) -0.001(5) 0.001(3)
C24 0.022(6) 0.069(8) 0.041(6) 0.013(6) 0.002(5) -0.007(6)
N 0.024(4) 0.020(4) 0.020(4) -0.005(3) -0.001(3) 0.002(3)
S 0.0144(10) 0.0288(11) 0.0333(13) 0.0029(9) -0.0019(8) 0.0019(9)
I 0.0235(3) 0.0238(3) 0.0349(3) -0.0003(4) 0.0018(4) -0.0014(2)
 
_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 N 1.311(12) . ?
C1 S 1.691(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(14) . ?
C2 C7 1.406(12) . ?
C2 S 1.738(10) . ?
C3 C4 1.378(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.357(14) . ?
C6 H6 0.9300 . ?
C7 N 1.421(13) . ?
C21 N 1.468(11) . ?
C21 C22 1.523(12) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.519(13) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.504(14) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
 
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
N C1 S 115.1(7) . . ?
N C1 H1 122.5 . . ?
S C1 H1 122.5 . . ?
C3 C2 C7 119.9(9) . . ?
C3 C2 S 128.7(7) . . ?
C7 C2 S 111.4(7) . . ?
C4 C3 C2 117.3(8) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 122.7(9) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C6 119.8(10) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 118.1(8) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C2 122.2(9) . . ?
C6 C7 N 127.8(8) . . ?
C2 C7 N 109.9(8) . . ?
N C21 C22 113.0(8) . . ?
N C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C21 109.5(8) . . ?
C23 C22 H22A 109.8 . . ?
C21 C22 H22A 109.8 . . ?
C23 C22 H22B 109.8 . . ?
C21 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
C24 C23 C22 111.7(8) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N C7 113.4(8) . . ?
C1 N C21 124.9(8) . . ?
C7 N C21 121.3(7) . . ?
C1 S C2 90.0(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.963
_diffrn_reflns_theta_full              28.09
_diffrn_measured_fraction_theta_full   0.963
_refine_diff_density_max    2.193
_refine_diff_density_min   -1.079
_refine_diff_density_rms    0.260
