data_03src0294
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H21 I4 N4 S3'
_chemical_formula_weight          909.18
 
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            Triclinic
_symmetry_space_group_name_H-M    P-1
_symmetry_space_group_name_hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    9.14320(10)
_cell_length_b                    9.9264(2)
_cell_length_c                    16.5802(3)
_cell_angle_alpha                 100.0980(10)
_cell_angle_beta                  95.7330(10)
_cell_angle_gamma                 110.7060(10)
_cell_volume                      1364.22(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     16740
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             dark
_exptl_crystal_size_max           0.14
_exptl_crystal_size_mid           0.13
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     2.213
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              846
_exptl_absorpt_coefficient_mu     4.812
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5523
_exptl_absorpt_correction_T_max   0.8308
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             11625
_diffrn_reflns_av_R_equivalents   0.0264
_diffrn_reflns_av_sigmaI/netI     0.0412
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          27.49
_reflns_number_total              6195
_reflns_number_gt                 5457
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_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)+(0.0478P)²+3.5475P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0023(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          6195
_refine_ls_number_parameters      280
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0422
_refine_ls_R_factor_gt            0.0367
_refine_ls_wR_factor_ref          0.0970
_refine_ls_wR_factor_gt           0.0925
_refine_ls_goodness_of_fit_ref    1.027
_refine_ls_restrained_S_all       1.027
_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
C13 C 0.1820(6) 0.5236(5) 0.4610(3) 0.0316(10) Uani 1 1 d . . .
H13 H 0.2253 0.5073 0.5112 0.038 Uiso 1 1 calc R . .
C14 C 0.2046(6) 0.6598(5) 0.4470(3) 0.0316(10) Uani 1 1 d . . .
H14 H 0.2653 0.7495 0.4864 0.038 Uiso 1 1 calc R . .
C15 C 0.1279(5) 0.6532(5) 0.3675(3) 0.0263(9) Uani 1 1 d . . .
H15 H 0.1309 0.7379 0.3475 0.032 Uiso 1 1 calc R . .
C16 C 0.0487(5) 0.5113(4) 0.3226(2) 0.0200(8) Uani 1 1 d . . .
C17 C -0.0467(4) 0.4657(4) 0.2399(2) 0.0179(7) Uani 1 1 d . . .
C18 C -0.2263(5) 0.3219(4) 0.1224(2) 0.0236(8) Uani 1 1 d . . .
H18A H -0.3401 0.2918 0.1269 0.028 Uiso 1 1 calc R . .
H18B H -0.2142 0.2530 0.0751 0.028 Uiso 1 1 calc R . .
C19 C -0.1557(5) 0.4828(5) 0.1132(3) 0.0283(9) Uani 1 1 d . . .
H19A H -0.0880 0.4925 0.0699 0.034 Uiso 1 1 calc R . .
H19B H -0.2403 0.5197 0.0992 0.034 Uiso 1 1 calc R . .
N3 N -0.1297(4) 0.3283(3) 0.2005(2) 0.0198(7) Uani 1 1 d D . .
N4 N -0.0614(4) 0.5619(4) 0.1959(2) 0.0210(7) Uani 1 1 d D . .
H3N H -0.132(8) 0.248(5) 0.224(4) 0.053(18) Uiso 1 1 d D . .
H4N H 0.005(4) 0.6632(16) 0.208(3) 0.013(10) Uiso 1 1 d D . .
C1 C 0.4384(6) 0.6994(5) 0.0719(3) 0.0323(10) Uani 1 1 d . . .
H1 H 0.4679 0.6178 0.0541 0.039 Uiso 1 1 calc R . .
C2 C 0.5135(5) 0.8347(5) 0.0591(3) 0.0289(9) Uani 1 1 d . . .
H2 H 0.6017 0.8589 0.0310 0.035 Uiso 1 1 calc R . .
C3 C 0.4476(5) 0.9393(4) 0.0921(2) 0.0217(8) Uani 1 1 d . . .
H3 H 0.4865 1.0403 0.0892 0.026 Uiso 1 1 calc R . .
C4 C 0.3185(4) 0.8722(4) 0.1290(2) 0.0184(7) Uani 1 1 d . . .
C5 C 0.2297(5) 0.9484(4) 0.1732(2) 0.0185(7) Uani 1 1 d . . .
H5 H 0.2607 1.0515 0.1765 0.022 Uiso 1 1 calc R . .
C6 C 0.0395(5) 0.9834(4) 0.2480(2) 0.0218(8) Uani 1 1 d . . .
H6A H 0.1097 1.0881 0.2544 0.026 Uiso 1 1 calc R . .
H6B H 0.0241 0.9658 0.3041 0.026 Uiso 1 1 calc R . .
C7 C -0.1197(5) 0.9519(4) 0.1954(2) 0.0207(8) Uani 1 1 d . . .
H7A H -0.1029 0.9794 0.1415 0.025 Uiso 1 1 calc R . .
H7B H -0.1853 0.8449 0.1840 0.025 Uiso 1 1 calc R . .
C8 C -0.3125(5) 0.9640(4) 0.2748(2) 0.0185(7) Uani 1 1 d . . .
H8 H -0.3318 0.8622 0.2707 0.022 Uiso 1 1 calc R . .
C9 C -0.4087(5) 1.0254(4) 0.3211(2) 0.0178(7) Uani 1 1 d . . .
C10 C -0.5161(5) 0.9531(4) 0.3671(3) 0.0241(8) Uani 1 1 d . . .
H10 H -0.5351 0.8551 0.3729 0.029 Uiso 1 1 calc R . .
C11 C -0.5949(5) 1.0408(5) 0.4046(3) 0.0268(9) Uani 1 1 d . . .
H11 H -0.6720 1.0086 0.4387 0.032 Uiso 1 1 calc R . .
C12 C -0.5475(5) 1.1767(5) 0.3861(3) 0.0245(8) Uani 1 1 d . . .
H12 H -0.5888 1.2495 0.4054 0.029 Uiso 1 1 calc R . .
N1 N 0.1139(4) 0.8861(3) 0.2076(2) 0.0189(6) Uani 1 1 d . . .
N2 N -0.2034(4) 1.0365(4) 0.2389(2) 0.0182(6) Uani 1 1 d . . .
S1 S 0.28334(15) 0.68996(12) 0.12379(8) 0.0353(3) Uani 1 1 d . . .
S2 S -0.40522(12) 1.20139(10) 0.32425(6) 0.0208(2) Uani 1 1 d . . .
S3 S 0.06683(14) 0.38478(12) 0.37803(7) 0.0295(2) Uani 1 1 d . . .
I1 I 0.35740(3) 0.39171(3) 0.191454(18) 0.02834(10) Uani 1 1 d . . .
I2 I 0.12818(4) 0.23004(4) 0.042970(19) 0.03543(11) Uani 1 1 d . . .
I3 I 0.58271(5) 0.56909(4) 0.34761(3) 0.05666(14) Uani 1 1 d . . .
I4 I 0.88114(4) 0.86880(3) 0.456525(18) 0.03158(10) 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
C13 C14 1.359(7) . ?
C13 S3 1.708(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.409(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.366(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.452(5) . ?
C16 S3 1.724(4) . ?
C17 N3 1.312(5) . ?
C17 N4 1.334(5) . ?
C18 N3 1.471(5) . ?
C18 C19 1.538(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N4 1.465(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
N3 H3N 0.946(10) . ?
N4 H4N 0.944(10) . ?
C1 C2 1.340(7) . ?
C1 S1 1.714(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.431(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.458(6) . ?
C4 S1 1.707(4) . ?
C5 N1 1.269(5) . ?
C5 H5 0.9500 . ?
C6 N1 1.474(5) . ?
C6 C7 1.520(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.471(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.275(5) . ?
C8 C9 1.444(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(6) . ?
C9 S2 1.728(4) . ?
C10 C11 1.418(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.364(6) . ?
C11 H11 0.9500 . ?
C12 S2 1.713(4) . ?
C12 H12 0.9500 . ?
I1 I2 2.8695(4) . ?
I1 I3 2.9696(5) . ?
I4 I4 2.7642(6) 2_776 ?
 
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
C14 C13 S3 112.4(3) . . ?
C14 C13 H13 123.8 . . ?
S3 C13 H13 123.8 . . ?
C13 C14 C15 112.5(4) . . ?
C13 C14 H14 123.8 . . ?
C15 C14 H14 123.8 . . ?
C16 C15 C14 112.5(4) . . ?
C16 C15 H15 123.8 . . ?
C14 C15 H15 123.8 . . ?
C15 C16 C17 126.5(4) . . ?
C15 C16 S3 111.6(3) . . ?
C17 C16 S3 121.9(3) . . ?
N3 C17 N4 112.2(3) . . ?
N3 C17 C16 125.0(3) . . ?
N4 C17 C16 122.7(3) . . ?
N3 C18 C19 102.0(3) . . ?
N3 C18 H18A 111.4 . . ?
C19 C18 H18A 111.4 . . ?
N3 C18 H18B 111.4 . . ?
C19 C18 H18B 111.4 . . ?
H18A C18 H18B 109.2 . . ?
N4 C19 C18 102.8(3) . . ?
N4 C19 H19A 111.2 . . ?
C18 C19 H19A 111.2 . . ?
N4 C19 H19B 111.2 . . ?
C18 C19 H19B 111.2 . . ?
H19A C19 H19B 109.1 . . ?
C17 N3 C18 110.8(3) . . ?
C17 N3 H3N 122(4) . . ?
C18 N3 H3N 127(4) . . ?
C17 N4 C19 110.0(3) . . ?
C17 N4 H4N 124(3) . . ?
C19 N4 H4N 123(3) . . ?
C2 C1 S1 112.5(3) . . ?
C2 C1 H1 123.7 . . ?
S1 C1 H1 123.7 . . ?
C1 C2 C3 113.3(4) . . ?
C1 C2 H2 123.3 . . ?
C3 C2 H2 123.3 . . ?
C4 C3 C2 110.6(4) . . ?
C4 C3 H3 124.7 . . ?
C2 C3 H3 124.7 . . ?
C3 C4 C5 125.1(3) . . ?
C3 C4 S1 112.0(3) . . ?
C5 C4 S1 122.7(3) . . ?
N1 C5 C4 124.3(3) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N1 C6 C7 109.5(3) . . ?
N1 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C6 110.3(3) . . ?
N2 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C9 124.7(4) . . ?
N2 C8 H8 117.7 . . ?
C9 C8 H8 117.7 . . ?
C10 C9 C8 125.5(4) . . ?
C10 C9 S2 111.0(3) . . ?
C8 C9 S2 123.4(3) . . ?
C9 C10 C11 112.7(4) . . ?
C9 C10 H10 123.7 . . ?
C11 C10 H10 123.7 . . ?
C12 C11 C10 112.3(4) . . ?
C12 C11 H11 123.9 . . ?
C10 C11 H11 123.9 . . ?
C11 C12 S2 112.4(3) . . ?
C11 C12 H12 123.8 . . ?
S2 C12 H12 123.8 . . ?
C5 N1 C6 115.5(3) . . ?
C8 N2 C7 115.5(3) . . ?
C4 S1 C1 91.6(2) . . ?
C12 S2 C9 91.6(2) . . ?
C13 S3 C16 91.1(2) . . ?
I2 I1 I3 176.618(14) . . ?
 
_diffrn_measured_fraction_theta_max    0.990
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.990
_refine_diff_density_max    1.283
_refine_diff_density_min   -1.559
_refine_diff_density_rms    0.158
