 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C9.50 H10.50 I1.50 N2 S1.50'
_chemical_formula_weight          391.14
 
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            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/n
_symmetry_space_group_name_hall   '-P 2yn'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    9.8236(2)
_cell_length_b                    27.4206(9)
_cell_length_c                    10.3335(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  111.113(2)
_cell_angle_gamma                 90.00
_cell_volume                      2596.67(13)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     11695
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        rod
_exptl_crystal_colour             orange
_exptl_crystal_size_max           0.60
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     2.001
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1480
_exptl_absorpt_coefficient_mu     3.866
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.2051
_exptl_absorpt_correction_T_max   0.7473
_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             22393
_diffrn_reflns_av_R_equivalents   0.0459
_diffrn_reflns_av_sigmaI/netI     0.0322
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -35
_diffrn_reflns_limit_k_max        35
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.97
_diffrn_reflns_theta_max          27.49
_reflns_number_total              5629
_reflns_number_gt                 4658
_reflns_threshold_expression      >2σ(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 > 2σ(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)+(0.0238P)²+2.0734P] 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        0.00052(8)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5629
_refine_ls_number_parameters      263
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0374
_refine_ls_R_factor_gt            0.0270
_refine_ls_wR_factor_ref          0.0633
_refine_ls_wR_factor_gt           0.0594
_refine_ls_goodness_of_fit_ref    1.046
_refine_ls_restrained_S_all       1.046
_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
N3 N 0.0914(3) 0.10320(10) 0.8091(3) 0.0354(6) Uani 1 1 d . . .
H31 H 0.0029 0.1118 0.8028 0.042 Uiso 1 1 calc R . .
C17 C 0.1233(3) 0.06487(13) 0.7269(3) 0.0383(8) Uani 1 1 d . . .
H17A H 0.0899 0.0740 0.6276 0.046 Uiso 1 1 calc R . .
H17B H 0.0768 0.0337 0.7363 0.046 Uiso 1 1 calc R . .
C18 C 0.2899(4) 0.06123(15) 0.7900(4) 0.0488(9) Uani 1 1 d . . .
H18A H 0.3211 0.0297 0.8385 0.059 Uiso 1 1 calc R . .
H18B H 0.3338 0.0648 0.7180 0.059 Uiso 1 1 calc R . .
N4 N 0.3295(3) 0.10178(10) 0.8870(3) 0.0353(6) Uani 1 1 d . . .
H32 H 0.4197 0.1108 0.9346 0.042 Uiso 1 1 calc R . .
C19 C 0.2127(3) 0.12334(11) 0.8945(3) 0.0319(7) Uani 1 1 d . . .
C1 C -0.1327(4) 0.20276(13) 0.3866(4) 0.0422(8) Uani 1 1 d . . .
H1 H -0.0662 0.2175 0.3507 0.051 Uiso 1 1 calc R . .
C2 C -0.2786(4) 0.20388(13) 0.3221(4) 0.0432(8) Uani 1 1 d . . .
H2 H -0.3265 0.2198 0.2359 0.052 Uiso 1 1 calc R . .
C3 C -0.3528(4) 0.17889(12) 0.3959(3) 0.0383(7) Uani 1 1 d . . .
H3 H -0.4559 0.1758 0.3644 0.046 Uiso 1 1 calc R . .
C4 C -0.2604(3) 0.15958(11) 0.5180(3) 0.0318(7) Uani 1 1 d . . .
C5 C -0.3037(3) 0.13451(11) 0.6195(3) 0.0326(7) Uani 1 1 d . . .
H5 H -0.4043 0.1272 0.5958 0.039 Uiso 1 1 calc R . .
C6 C -0.2824(4) 0.09895(13) 0.8307(3) 0.0382(7) Uani 1 1 d . . .
H6A H -0.2195 0.0720 0.8828 0.046 Uiso 1 1 calc R . .
H6B H -0.3790 0.0852 0.7750 0.046 Uiso 1 1 calc R . .
C7 C -0.2996(4) 0.13657(12) 0.9315(3) 0.0370(7) Uani 1 1 d . . .
H7A H -0.2036 0.1513 0.9847 0.044 Uiso 1 1 calc R . .
H7B H -0.3659 0.1629 0.8797 0.044 Uiso 1 1 calc R . .
C8 C -0.2680(3) 0.09801(12) 1.1422(3) 0.0348(7) Uani 1 1 d . . .
H8 H -0.1674 0.1047 1.1632 0.042 Uiso 1 1 calc R . .
C9 C -0.3103(3) 0.07159(12) 1.2422(3) 0.0350(7) Uani 1 1 d . . .
C10 C -0.2125(4) 0.05275(11) 1.3731(3) 0.0356(7) Uani 1 1 d . . .
H10 H -0.1091 0.0553 1.4078 0.043 Uiso 1 1 calc R . .
C11 C -0.2984(4) 0.02966(14) 1.4412(4) 0.0515(10) Uani 1 1 d . . .
H11 H -0.2567 0.0150 1.5301 0.062 Uiso 1 1 calc R . .
C12 C -0.4439(4) 0.03025(14) 1.3692(4) 0.0483(9) Uani 1 1 d . . .
H12 H -0.5134 0.0160 1.4022 0.058 Uiso 1 1 calc R . .
C13 C 0.1658(4) 0.22965(13) 1.1197(4) 0.0444(8) Uani 1 1 d . . .
H13 H 0.1248 0.2539 1.1603 0.053 Uiso 1 1 calc R . .
C14 C 0.3103(4) 0.22184(12) 1.1576(4) 0.0419(8) Uani 1 1 d . . .
H14 H 0.3815 0.2401 1.2280 0.050 Uiso 1 1 calc R . .
C15 C 0.3459(3) 0.18373(11) 1.0825(3) 0.0297(6) Uani 1 1 d . . .
H15 H 0.4424 0.1735 1.0958 0.036 Uiso 1 1 calc R . .
C16 C 0.2197(3) 0.16341(11) 0.9863(3) 0.0319(7) Uani 1 1 d . . .
N1 N -0.2169(3) 0.12156(10) 0.7383(3) 0.0338(6) Uani 1 1 d . . .
N2 N -0.3596(3) 0.11289(10) 1.0266(3) 0.0332(6) Uani 1 1 d . . .
S1 S -0.08047(9) 0.17170(3) 0.54091(9) 0.03727(19) Uani 1 1 d . . .
S2 S -0.48970(10) 0.05928(4) 1.21336(10) 0.0462(2) Uani 1 1 d . . .
S3 S 0.06544(10) 0.19180(3) 0.99200(10) 0.0443(2) Uani 1 1 d . . .
I1 I 0.21056(2) 0.115741(8) 0.36998(2) 0.03601(7) Uani 1 1 d . . .
I2 I 0.11365(2) 0.039102(8) 0.16224(2) 0.04076(8) Uani 1 1 d . . .
I3 I 0.30509(3) 0.195254(10) 0.57462(3) 0.05214(9) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N3 C19 1.322(4) . ?
N3 C17 1.455(4) . ?
N3 H31 0.8800 . ?
C17 C18 1.531(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N4 1.453(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N4 C19 1.318(4) . ?
N4 H32 0.8800 . ?
C19 C16 1.437(5) . ?
C1 C2 1.346(5) . ?
C1 S1 1.715(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.408(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.368(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.441(4) . ?
C4 S1 1.729(3) . ?
C5 N1 1.267(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.466(4) . ?
C6 C7 1.518(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.467(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.276(4) . ?
C8 C9 1.440(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.443(5) . ?
C9 S2 1.712(3) . ?
C10 C11 1.427(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.353(5) . ?
C11 H11 0.9500 . ?
C12 S2 1.705(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.346(5) . ?
C13 S3 1.689(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.419(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(4) . ?
C15 H15 0.9500 . ?
C16 S3 1.724(3) . ?
I1 I2 2.9084(3) . ?
I1 I3 2.9450(3) . ?
 
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
C19 N3 C17 111.1(3) . . ?
C19 N3 H31 124.5 . . ?
C17 N3 H31 124.5 . . ?
N3 C17 C18 102.7(3) . . ?
N3 C17 H17A 111.2 . . ?
C18 C17 H17A 111.2 . . ?
N3 C17 H17B 111.2 . . ?
C18 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
N4 C18 C17 102.9(3) . . ?
N4 C18 H18A 111.2 . . ?
C17 C18 H18A 111.2 . . ?
N4 C18 H18B 111.2 . . ?
C17 C18 H18B 111.2 . . ?
H18A C18 H18B 109.1 . . ?
C19 N4 C18 111.2(3) . . ?
C19 N4 H32 124.4 . . ?
C18 N4 H32 124.4 . . ?
N4 C19 N3 111.6(3) . . ?
N4 C19 C16 123.1(3) . . ?
N3 C19 C16 125.3(3) . . ?
C2 C1 S1 112.4(3) . . ?
C2 C1 H1 123.8 . . ?
S1 C1 H1 123.8 . . ?
C1 C2 C3 112.8(3) . . ?
C1 C2 H2 123.6 . . ?
C3 C2 H2 123.6 . . ?
C4 C3 C2 112.8(3) . . ?
C4 C3 H3 123.6 . . ?
C2 C3 H3 123.6 . . ?
C3 C4 C5 125.8(3) . . ?
C3 C4 S1 111.0(2) . . ?
C5 C4 S1 123.2(2) . . ?
N1 C5 C4 124.5(3) . . ?
N1 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
N1 C6 C7 110.0(3) . . ?
N1 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C6 109.2(3) . . ?
N2 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
N2 C8 C9 123.0(3) . . ?
N2 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
C8 C9 C10 125.9(3) . . ?
C8 C9 S2 121.3(2) . . ?
C10 C9 S2 112.9(2) . . ?
C11 C10 C9 108.0(3) . . ?
C11 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
C12 C11 C10 114.8(3) . . ?
C12 C11 H11 122.6 . . ?
C10 C11 H11 122.6 . . ?
C11 C12 S2 113.1(3) . . ?
C11 C12 H12 123.5 . . ?
S2 C12 H12 123.5 . . ?
C14 C13 S3 112.8(3) . . ?
C14 C13 H13 123.6 . . ?
S3 C13 H13 123.6 . . ?
C13 C14 C15 113.6(3) . . ?
C13 C14 H14 123.2 . . ?
C15 C14 H14 123.2 . . ?
C16 C15 C14 110.7(3) . . ?
C16 C15 H15 124.7 . . ?
C14 C15 H15 124.7 . . ?
C15 C16 C19 126.5(3) . . ?
C15 C16 S3 111.2(2) . . ?
C19 C16 S3 122.3(2) . . ?
C5 N1 C6 116.7(3) . . ?
C8 N2 C7 116.8(3) . . ?
C1 S1 C4 91.10(16) . . ?
C12 S2 C9 91.31(18) . . ?
C13 S3 C16 91.77(17) . . ?
I2 I1 I3 178.496(11) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C19 N3 C17 C18 6.2(4) . . . . ?
N3 C17 C18 N4 -6.6(4) . . . . ?
C17 C18 N4 C19 5.5(4) . . . . ?
C18 N4 C19 N3 -1.8(4) . . . . ?
C18 N4 C19 C16 177.6(3) . . . . ?
C17 N3 C19 N4 -3.1(4) . . . . ?
C17 N3 C19 C16 177.5(3) . . . . ?
S1 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 176.3(3) . . . . ?
C2 C3 C4 S1 -0.7(4) . . . . ?
C3 C4 C5 N1 -172.0(3) . . . . ?
S1 C4 C5 N1 4.6(5) . . . . ?
N1 C6 C7 N2 -177.7(2) . . . . ?
N2 C8 C9 C10 178.5(3) . . . . ?
N2 C8 C9 S2 -1.4(5) . . . . ?
C8 C9 C10 C11 179.2(3) . . . . ?
S2 C9 C10 C11 -1.0(3) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 S2 -0.5(5) . . . . ?
S3 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C19 -178.3(3) . . . . ?
C14 C15 C16 S3 0.3(3) . . . . ?
N4 C19 C16 C15 -2.9(5) . . . . ?
N3 C19 C16 C15 176.5(3) . . . . ?
N4 C19 C16 S3 178.7(2) . . . . ?
N3 C19 C16 S3 -1.9(5) . . . . ?
C4 C5 N1 C6 176.5(3) . . . . ?
C7 C6 N1 C5 -98.1(3) . . . . ?
C9 C8 N2 C7 -176.2(3) . . . . ?
C6 C7 N2 C8 94.2(3) . . . . ?
C2 C1 S1 C4 0.2(3) . . . . ?
C3 C4 S1 C1 0.3(3) . . . . ?
C5 C4 S1 C1 -176.8(3) . . . . ?
C11 C12 S2 C9 0.0(3) . . . . ?
C8 C9 S2 C12 -179.6(3) . . . . ?
C10 C9 S2 C12 0.6(3) . . . . ?
C14 C13 S3 C16 0.2(3) . . . . ?
C15 C16 S3 C13 -0.2(3) . . . . ?
C19 C16 S3 C13 178.4(3) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.944
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.944
_refine_diff_density_max    0.736
_refine_diff_density_min   -0.722
_refine_diff_density_rms    0.089
