This work presents a single-crystal X-ray diffraction study of an organic co-crystal composed of
N-iodosaccharin and pyridine (NISac·py) under hydrostatic pressure ranging from 0.00 (5) GPa to 4.5 (2) GPa. NISac·py crystallizes in the monoclinic system (space group
B2
1/
e). The unconventional setting of the space group is adopted (the conventional setting is
P2
1/
c, No. 14) to emphasise the strongly pseudo-orthorhombic symmetry of the lattice, with a β angle very close to 90°. The crystal structure contains one molecule each of
N-iodosaccharin (NISac) and pyridine (py) in the asymmetric unit (
Z′ = 1), linked via an N
sacI
N′
py halogen-bonding motif. A gradual modification of this motif is observed under pressure as a result of changes in the crystalline environment. Mechanical twinning is observed under compression and the sample splits into two domains, spanning an unequal volume that is mapped by a twofold rotation about the [100] direction of the
B2
1/
e unit cell. The twinning is particularly significant at high pressure, being reversible when the pressure is released. The structure of the twinned sample reveals the continuity of a substantial substructure across the composition plane. The presence of this common substructure in the two orientations of the twinned individuals can be interpreted as a structural reason for the formation of the twin and is the first observed example in a molecular crystal. These results indicate that the anisotropy of intermolecular interactions in the crystal structure results in an anisotropic strain generated upon the action of hydrostatic compression. Periodic density functional theory calculations were carried out by considering an isotropic external pressure, the results showing good agreement with the experimental findings. The bulk modulus of the crystal was obtained from the equations of state, being 7 (1) GPa for experimental data and 6.8 (5) GPa for theoretical data.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520622002542/rm5056sup1.cif Contains datablocks global, NISac_Py_crystal_1_RTP, NISac_Py_crystal_1_100K, dac_0.00_GPa, dac_0.00_d_GPa, dac_0.05_d_GPa, dac_0.20_GPa, dac_0.4_GPa, dac_0.5_GPa, dac_0.5_d_GPa, dac_0.8_d_GPa, dac_0.9_GPa, dac_1.3_d_GPa, dac_1.5_GPa, dac_1.9_d_GPa, dac_2.0_GPa, dac_2.4_d_GPa, dac_3.3_GPa, dac_4.5_GPa, NISac_Py_crystal_2_RTP |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056NISac_Py_crystal_1_RTPsup2.hkl Contains datablock NISac_Py_crystal_1_RTP |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056NISac_Py_crystal_1_100Ksup3.hkl Contains datablock NISac_Py_crystal_1_100K |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_0.00_GPasup4.hkl Contains datablock dac_0.00_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_0.00_d_GPasup5.hkl Contains datablock dac_0.00_d_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_0.05_d_GPasup6.hkl Contains datablock dac_0.05_d_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_0.20_GPasup7.hkl Contains datablock dac_0.20_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_0.4_GPasup8.hkl Contains datablock dac_0.4_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_0.5_GPasup9.hkl Contains datablock dac_0.5_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_0.5_d_GPasup10.hkl Contains datablock dac_0.5_d_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_0.8_d_GPasup11.hkl Contains datablock dac_0.8_d_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_0.9_GPasup12.hkl Contains datablock dac_0.9_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_1.3_d_GPasup13.hkl Contains datablock dac_1.3_d_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_1.5_GPasup14.hkl Contains datablock dac_1.5_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_1.9_d_GPasup15.hkl Contains datablock dac_1.9_d_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_2.0_GPasup16.hkl Contains datablock dac_2.0_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_2.4_d_GPasup17.hkl Contains datablock dac_2.4_d_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_3.3_GPasup18.hkl Contains datablock dac_3.3_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056dac_4.5_GPasup19.hkl Contains datablock dac_4.5_GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002542/rm5056NISac_Py_crystal_2_RTPsup20.hkl Contains datablock NISac_Py_crystal_2_RTP |
| Portable Document Format (PDF) file https://doi.org/10.1107/S2052520622002542/rm5056sup21.pdf Additional tables and figures |
CCDC references: 2156534; 2156535; 2156536; 2156537; 2156538; 2156539; 2156540; 2156541; 2156542; 2156543; 2156544; 2156545; 2156546; 2156547; 2156548; 2156549; 2156550; 2156551; 2156552
For all structures, cell refinement: SAINT V8.40B (?, 2016); data reduction: SAINT V8.40B (?, 2016). Program(s) used to solve structure: XT (Sheldrick, 2015) for NISac_Py_crystal_1_RTP; SHELXT (Sheldrick, 2015) for NISac_Py_crystal_1_100K, dac_0.00_GPa, dac_0.00_d_GPa, dac_0.05_d_GPa, dac_0.20_GPa, dac_0.4_GPa, dac_0.5_GPa, dac_0.5_d_GPa, dac_0.8_d_GPa, dac_0.9_GPa, dac_1.3_d_GPa, dac_1.5_GPa, dac_1.9_d_GPa, dac_2.0_GPa, dac_2.4_d_GPa, dac_3.3_GPa, dac_4.5_GPa, NISac_Py_crystal_2_RTP. For all structures, program(s) used to refine structure: SHELXL 2014/3 (Sheldrick, 2015); molecular graphics: Olex2 1.3 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009).
(NISac_Py_crystal_1_RTP)
top
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 1.922 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 27.234 (3) Å | Cell parameters from 9068 reflections |
b = 7.8058 (7) Å | θ = 3.0–35.3° |
c = 12.6258 (10) Å | µ = 2.55 mm−1 |
β = 88.606 (2)° | T = 296 K |
V = 2683.2 (4) Å3 | Plate, colourless |
Z = 8 | 0.15 × 0.12 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3456 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.034 |
Absorption correction: numerical SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0765 before and 0.0552 after correction.
The Ratio of minimum to maximum transmission is 0.8748.
The λ/2 correction factor is Not present. | θmax = 29.6°, θmin = 1.8° |
Tmin = 0.569, Tmax = 0.650 | h = −37→37 |
109428 measured reflections | k = −10→10 |
3759 independent reflections | l = −17→17 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.019 | H-atom parameters constrained |
wR(F2) = 0.050 | w = 1/[σ2(Fo2) + (0.021P)2 + 3.1655P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
3759 reflections | Δρmax = 0.73 e Å−3 |
173 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28444 (2) | 0.39783 (2) | 0.47942 (2) | 0.03977 (5) | |
S1 | 0.40406 (2) | 0.47307 (7) | 0.44942 (4) | 0.04072 (10) | |
N2 | 0.21598 (6) | 0.3842 (2) | 0.58768 (13) | 0.0402 (3) | |
O3 | 0.32802 (6) | 0.4083 (2) | 0.21415 (13) | 0.0553 (4) | |
O1 | 0.39561 (7) | 0.6158 (2) | 0.51840 (13) | 0.0625 (5) | |
C7 | 0.35993 (7) | 0.4390 (3) | 0.27664 (15) | 0.0383 (4) | |
C4 | 0.48580 (8) | 0.5932 (3) | 0.32890 (19) | 0.0478 (5) | |
H4 | 0.5042 | 0.6114 | 0.3890 | 0.057* | |
C10 | 0.13886 (9) | 0.4130 (3) | 0.73070 (18) | 0.0524 (5) | |
H10 | 0.1129 | 0.4243 | 0.7794 | 0.063* | |
N1 | 0.35443 (6) | 0.4241 (2) | 0.38535 (13) | 0.0423 (4) | |
C12 | 0.22003 (8) | 0.3230 (3) | 0.68637 (17) | 0.0478 (4) | |
H12 | 0.2491 | 0.2702 | 0.7057 | 0.057* | |
C5 | 0.43830 (6) | 0.5306 (2) | 0.33556 (14) | 0.0360 (3) | |
O2 | 0.42466 (6) | 0.3224 (2) | 0.49619 (13) | 0.0601 (4) | |
C6 | 0.41043 (6) | 0.5012 (2) | 0.24767 (14) | 0.0358 (3) | |
C9 | 0.13468 (8) | 0.4724 (3) | 0.62862 (18) | 0.0510 (5) | |
H9 | 0.1056 | 0.5226 | 0.6070 | 0.061* | |
C2 | 0.47715 (9) | 0.5993 (3) | 0.13878 (19) | 0.0557 (6) | |
H2 | 0.4906 | 0.6243 | 0.0721 | 0.067* | |
C8 | 0.17421 (7) | 0.4566 (3) | 0.55872 (16) | 0.0426 (4) | |
H8 | 0.1715 | 0.4974 | 0.4899 | 0.051* | |
C1 | 0.42997 (8) | 0.5343 (3) | 0.14777 (16) | 0.0498 (5) | |
H1 | 0.4118 | 0.5133 | 0.0878 | 0.060* | |
C11 | 0.18199 (9) | 0.3367 (3) | 0.75955 (17) | 0.0519 (5) | |
H11 | 0.1854 | 0.2949 | 0.8279 | 0.062* | |
C3 | 0.50463 (8) | 0.6275 (3) | 0.2281 (2) | 0.0545 (5) | |
H3 | 0.5364 | 0.6703 | 0.2202 | 0.065* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.03320 (7) | 0.04341 (7) | 0.04262 (7) | −0.00149 (4) | 0.00078 (5) | 0.00083 (5) |
S1 | 0.0367 (2) | 0.0537 (3) | 0.0320 (2) | −0.00646 (19) | −0.00651 (16) | 0.00200 (19) |
N2 | 0.0360 (8) | 0.0430 (8) | 0.0415 (8) | −0.0028 (6) | 0.0029 (6) | 0.0001 (6) |
O3 | 0.0387 (7) | 0.0817 (12) | 0.0462 (8) | −0.0091 (7) | −0.0127 (6) | −0.0057 (7) |
O1 | 0.0696 (11) | 0.0758 (12) | 0.0420 (8) | −0.0127 (9) | 0.0034 (7) | −0.0164 (8) |
C7 | 0.0316 (8) | 0.0463 (10) | 0.0371 (9) | 0.0005 (7) | −0.0037 (6) | −0.0033 (7) |
C4 | 0.0363 (10) | 0.0527 (12) | 0.0547 (12) | −0.0087 (8) | −0.0071 (8) | −0.0005 (9) |
C10 | 0.0508 (12) | 0.0609 (13) | 0.0449 (11) | −0.0025 (10) | 0.0129 (9) | −0.0031 (9) |
N1 | 0.0303 (7) | 0.0604 (10) | 0.0363 (8) | −0.0048 (7) | −0.0026 (6) | 0.0014 (7) |
C12 | 0.0471 (11) | 0.0489 (11) | 0.0475 (11) | 0.0012 (9) | −0.0042 (8) | 0.0055 (9) |
C5 | 0.0321 (8) | 0.0395 (9) | 0.0366 (8) | −0.0019 (7) | −0.0037 (6) | 0.0005 (7) |
O2 | 0.0532 (9) | 0.0698 (11) | 0.0580 (9) | −0.0054 (8) | −0.0174 (7) | 0.0227 (8) |
C6 | 0.0302 (8) | 0.0412 (9) | 0.0361 (8) | 0.0020 (7) | −0.0026 (6) | −0.0022 (7) |
C9 | 0.0389 (10) | 0.0636 (13) | 0.0502 (11) | 0.0062 (9) | 0.0024 (8) | −0.0002 (10) |
C2 | 0.0521 (12) | 0.0656 (15) | 0.0488 (12) | −0.0025 (10) | 0.0136 (10) | 0.0070 (10) |
C8 | 0.0370 (9) | 0.0520 (11) | 0.0387 (9) | −0.0010 (8) | 0.0002 (7) | 0.0016 (8) |
C1 | 0.0468 (11) | 0.0663 (14) | 0.0363 (9) | 0.0000 (10) | −0.0005 (8) | −0.0010 (9) |
C11 | 0.0610 (13) | 0.0558 (12) | 0.0387 (10) | −0.0050 (10) | 0.0011 (9) | 0.0062 (9) |
C3 | 0.0390 (10) | 0.0543 (13) | 0.0699 (15) | −0.0101 (9) | 0.0085 (10) | 0.0038 (11) |
Geometric parameters (Å, º) top
I1—N2 | 2.2875 (16) | C10—C9 | 1.377 (3) |
I1—N1 | 2.2305 (16) | C10—C11 | 1.374 (3) |
S1—O1 | 1.4292 (17) | C12—H12 | 0.9300 |
S1—N1 | 1.6371 (16) | C12—C11 | 1.376 (3) |
S1—C5 | 1.7529 (19) | C5—C6 | 1.379 (2) |
S1—O2 | 1.4365 (18) | C6—C1 | 1.381 (3) |
N2—C12 | 1.342 (3) | C9—H9 | 0.9300 |
N2—C8 | 1.329 (3) | C9—C8 | 1.381 (3) |
O3—C7 | 1.212 (2) | C2—H2 | 0.9300 |
C7—N1 | 1.382 (2) | C2—C1 | 1.384 (3) |
C7—C6 | 1.495 (2) | C2—C3 | 1.386 (4) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.384 (3) | C1—H1 | 0.9300 |
C4—C3 | 1.387 (3) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N1—I1—N2 | 174.88 (6) | C4—C5—S1 | 128.20 (15) |
O1—S1—N1 | 111.13 (11) | C6—C5—S1 | 108.97 (13) |
O1—S1—C5 | 111.99 (10) | C6—C5—C4 | 122.83 (18) |
O1—S1—O2 | 116.52 (11) | C5—C6—C7 | 112.23 (16) |
N1—S1—C5 | 94.80 (8) | C5—C6—C1 | 119.76 (17) |
O2—S1—N1 | 110.34 (10) | C1—C6—C7 | 127.99 (17) |
O2—S1—C5 | 109.97 (10) | C10—C9—H9 | 120.4 |
C12—N2—I1 | 119.15 (14) | C10—C9—C8 | 119.2 (2) |
C8—N2—I1 | 120.43 (13) | C8—C9—H9 | 120.4 |
C8—N2—C12 | 119.82 (18) | C1—C2—H2 | 119.7 |
O3—C7—N1 | 124.61 (18) | C1—C2—C3 | 120.7 (2) |
O3—C7—C6 | 125.08 (18) | C3—C2—H2 | 119.7 |
N1—C7—C6 | 110.30 (15) | N2—C8—C9 | 121.41 (19) |
C5—C4—H4 | 121.7 | N2—C8—H8 | 119.3 |
C5—C4—C3 | 116.6 (2) | C9—C8—H8 | 119.3 |
C3—C4—H4 | 121.7 | C6—C1—C2 | 118.7 (2) |
C9—C10—H10 | 120.5 | C6—C1—H1 | 120.7 |
C11—C10—H10 | 120.5 | C2—C1—H1 | 120.7 |
C11—C10—C9 | 119.0 (2) | C10—C11—C12 | 119.4 (2) |
S1—N1—I1 | 117.61 (9) | C10—C11—H11 | 120.3 |
C7—N1—I1 | 127.38 (12) | C12—C11—H11 | 120.3 |
C7—N1—S1 | 113.60 (13) | C4—C3—H3 | 119.3 |
N2—C12—H12 | 119.4 | C2—C3—C4 | 121.4 (2) |
N2—C12—C11 | 121.2 (2) | C2—C3—H3 | 119.3 |
C11—C12—H12 | 119.4 | | |
| | | |
I1—N2—C12—C11 | 169.76 (17) | N1—C7—C6—C1 | −179.1 (2) |
I1—N2—C8—C9 | −170.26 (17) | C12—N2—C8—C9 | 0.8 (3) |
S1—C5—C6—C7 | 2.8 (2) | C5—S1—N1—I1 | −164.79 (10) |
S1—C5—C6—C1 | −178.93 (17) | C5—S1—N1—C7 | 2.66 (16) |
N2—C12—C11—C10 | 0.7 (4) | C5—C4—C3—C2 | −0.3 (3) |
O3—C7—N1—I1 | −14.5 (3) | C5—C6—C1—C2 | −1.0 (3) |
O3—C7—N1—S1 | 179.57 (18) | O2—S1—N1—I1 | 81.83 (13) |
O3—C7—C6—C5 | 178.0 (2) | O2—S1—N1—C7 | −110.72 (16) |
O3—C7—C6—C1 | −0.1 (3) | O2—S1—C5—C4 | −68.5 (2) |
O1—S1—N1—I1 | −48.99 (14) | O2—S1—C5—C6 | 110.52 (15) |
O1—S1—N1—C7 | 118.46 (16) | C6—C7—N1—I1 | 164.55 (13) |
O1—S1—C5—C4 | 62.8 (2) | C6—C7—N1—S1 | −1.4 (2) |
O1—S1—C5—C6 | −118.25 (15) | C9—C10—C11—C12 | 0.6 (4) |
C7—C6—C1—C2 | 176.9 (2) | C8—N2—C12—C11 | −1.4 (3) |
C4—C5—C6—C7 | −178.15 (19) | C1—C2—C3—C4 | −0.6 (4) |
C4—C5—C6—C1 | 0.1 (3) | C11—C10—C9—C8 | −1.2 (4) |
C10—C9—C8—N2 | 0.5 (4) | C3—C4—C5—S1 | 179.41 (18) |
N1—S1—C5—C4 | 177.9 (2) | C3—C4—C5—C6 | 0.6 (3) |
N1—S1—C5—C6 | −3.16 (15) | C3—C2—C1—C6 | 1.2 (4) |
N1—C7—C6—C5 | −1.0 (2) | | |
(NISac_Py_crystal_1_100K)
top
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 1.986 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 27.085 (5) Å | Cell parameters from 9083 reflections |
b = 7.6524 (9) Å | θ = 3.0–39.5° |
c = 12.5325 (14) Å | µ = 2.63 mm−1 |
β = 88.571 (2)° | T = 296 K |
V = 2596.7 (6) Å3 | Plate, colourless |
Z = 8 | 0.15 × 0.12 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | Rint = 0.031 |
φ and ω scans | θmax = 29.6°, θmin = 1.8° |
104622 measured reflections | h = −37→37 |
3643 independent reflections | k = −10→10 |
3587 reflections with I > 2σ(I) | l = −17→17 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.015 | H-atom parameters constrained |
wR(F2) = 0.038 | w = 1/[σ2(Fo2) + (0.0114P)2 + 7.3244P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max = 0.004 |
3643 reflections | Δρmax = 1.04 e Å−3 |
173 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28300 (2) | 0.39845 (2) | 0.47823 (2) | 0.01169 (3) | |
S1 | 0.40329 (2) | 0.47536 (5) | 0.44910 (3) | 0.01222 (7) | |
N2 | 0.21478 (5) | 0.38605 (17) | 0.58721 (11) | 0.0132 (2) | |
O3 | 0.32790 (4) | 0.40777 (17) | 0.20950 (9) | 0.0175 (2) | |
O1 | 0.39427 (5) | 0.62153 (17) | 0.51888 (10) | 0.0197 (2) | |
C7 | 0.35965 (6) | 0.4398 (2) | 0.27347 (12) | 0.0125 (3) | |
C4 | 0.48635 (6) | 0.5980 (2) | 0.33047 (13) | 0.0156 (3) | |
H4 | 0.5043 | 0.6168 | 0.3917 | 0.019* | |
C10 | 0.13715 (6) | 0.4168 (2) | 0.73237 (13) | 0.0170 (3) | |
H10 | 0.1111 | 0.4288 | 0.7815 | 0.020* | |
N1 | 0.35361 (5) | 0.42507 (19) | 0.38311 (10) | 0.0138 (2) | |
C12 | 0.21934 (6) | 0.3238 (2) | 0.68716 (13) | 0.0154 (3) | |
H12 | 0.2487 | 0.2703 | 0.7062 | 0.018* | |
C5 | 0.43843 (5) | 0.5348 (2) | 0.33531 (12) | 0.0120 (3) | |
O2 | 0.42387 (4) | 0.32142 (17) | 0.49739 (10) | 0.0186 (2) | |
C6 | 0.41078 (5) | 0.5040 (2) | 0.24556 (12) | 0.0116 (3) | |
C9 | 0.13275 (6) | 0.4770 (2) | 0.62844 (13) | 0.0162 (3) | |
H9 | 0.1035 | 0.5280 | 0.6068 | 0.019* | |
C2 | 0.47903 (6) | 0.6025 (2) | 0.13742 (14) | 0.0179 (3) | |
H2 | 0.4931 | 0.6268 | 0.0706 | 0.021* | |
C8 | 0.17250 (6) | 0.4601 (2) | 0.55732 (12) | 0.0137 (3) | |
H8 | 0.1698 | 0.5008 | 0.4878 | 0.016* | |
C1 | 0.43103 (6) | 0.5370 (2) | 0.14481 (13) | 0.0155 (3) | |
H1 | 0.4131 | 0.5161 | 0.0838 | 0.019* | |
C11 | 0.18099 (6) | 0.3385 (2) | 0.76177 (13) | 0.0164 (3) | |
H11 | 0.1846 | 0.2964 | 0.8308 | 0.020* | |
C3 | 0.50623 (6) | 0.6319 (2) | 0.22873 (14) | 0.0171 (3) | |
H3 | 0.5383 | 0.6750 | 0.2217 | 0.021* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.01003 (5) | 0.01246 (5) | 0.01256 (5) | −0.00041 (3) | 0.00017 (3) | 0.00047 (3) |
S1 | 0.01159 (15) | 0.01520 (17) | 0.00996 (15) | −0.00183 (13) | −0.00207 (12) | 0.00053 (13) |
N2 | 0.0127 (6) | 0.0132 (6) | 0.0137 (6) | −0.0015 (5) | 0.0008 (5) | −0.0004 (5) |
O3 | 0.0138 (5) | 0.0235 (6) | 0.0153 (5) | −0.0029 (4) | −0.0041 (4) | −0.0011 (4) |
O1 | 0.0228 (6) | 0.0221 (6) | 0.0140 (5) | −0.0034 (5) | 0.0008 (4) | −0.0049 (5) |
C7 | 0.0116 (6) | 0.0130 (6) | 0.0128 (6) | 0.0008 (5) | −0.0005 (5) | −0.0003 (5) |
C4 | 0.0134 (7) | 0.0156 (7) | 0.0180 (7) | −0.0019 (5) | −0.0028 (5) | −0.0010 (6) |
C10 | 0.0181 (7) | 0.0186 (7) | 0.0141 (7) | −0.0016 (6) | 0.0034 (6) | −0.0014 (6) |
N1 | 0.0106 (6) | 0.0197 (6) | 0.0112 (6) | −0.0021 (5) | −0.0007 (4) | 0.0004 (5) |
C12 | 0.0158 (7) | 0.0145 (7) | 0.0159 (7) | −0.0001 (6) | −0.0018 (5) | 0.0012 (6) |
C5 | 0.0117 (6) | 0.0122 (6) | 0.0121 (6) | 0.0002 (5) | −0.0007 (5) | −0.0002 (5) |
O2 | 0.0177 (5) | 0.0199 (6) | 0.0184 (6) | −0.0012 (5) | −0.0058 (4) | 0.0063 (5) |
C6 | 0.0098 (6) | 0.0121 (6) | 0.0128 (6) | 0.0006 (5) | −0.0009 (5) | 0.0003 (5) |
C9 | 0.0134 (7) | 0.0189 (7) | 0.0165 (7) | 0.0020 (6) | −0.0004 (5) | −0.0004 (6) |
C2 | 0.0172 (7) | 0.0188 (8) | 0.0174 (7) | −0.0013 (6) | 0.0042 (6) | 0.0020 (6) |
C8 | 0.0127 (6) | 0.0156 (7) | 0.0129 (6) | −0.0015 (5) | −0.0010 (5) | 0.0006 (5) |
C1 | 0.0152 (7) | 0.0185 (7) | 0.0129 (7) | 0.0000 (6) | −0.0002 (5) | −0.0005 (6) |
C11 | 0.0205 (7) | 0.0163 (7) | 0.0124 (7) | −0.0019 (6) | −0.0003 (6) | 0.0019 (6) |
C3 | 0.0124 (7) | 0.0151 (7) | 0.0238 (8) | −0.0031 (6) | 0.0026 (6) | 0.0001 (6) |
Geometric parameters (Å, º) top
I1—N2 | 2.2722 (14) | C10—C9 | 1.389 (2) |
I1—N1 | 2.2375 (13) | C10—C11 | 1.388 (2) |
S1—O1 | 1.4370 (13) | C12—H12 | 0.9300 |
S1—N1 | 1.6426 (14) | C12—C11 | 1.385 (2) |
S1—C5 | 1.7546 (16) | C5—C6 | 1.387 (2) |
S1—O2 | 1.4428 (12) | C6—C1 | 1.387 (2) |
N2—C12 | 1.348 (2) | C9—H9 | 0.9300 |
N2—C8 | 1.339 (2) | C9—C8 | 1.386 (2) |
O3—C7 | 1.2151 (19) | C2—H2 | 0.9300 |
C7—N1 | 1.3842 (19) | C2—C1 | 1.394 (2) |
C7—C6 | 1.503 (2) | C2—C3 | 1.395 (2) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.385 (2) | C1—H1 | 0.9300 |
C4—C3 | 1.396 (2) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N1—I1—N2 | 174.57 (5) | C4—C5—S1 | 127.94 (12) |
O1—S1—N1 | 111.09 (8) | C4—C5—C6 | 123.24 (14) |
O1—S1—C5 | 111.92 (8) | C6—C5—S1 | 108.80 (11) |
O1—S1—O2 | 116.23 (8) | C5—C6—C7 | 112.33 (13) |
N1—S1—C5 | 94.93 (7) | C5—C6—C1 | 119.86 (14) |
O2—S1—N1 | 110.48 (7) | C1—C6—C7 | 127.79 (14) |
O2—S1—C5 | 110.19 (7) | C10—C9—H9 | 120.4 |
C12—N2—I1 | 118.75 (11) | C8—C9—C10 | 119.25 (15) |
C8—N2—I1 | 120.16 (10) | C8—C9—H9 | 120.4 |
C8—N2—C12 | 120.52 (14) | C1—C2—H2 | 119.5 |
O3—C7—N1 | 124.78 (14) | C1—C2—C3 | 120.95 (15) |
O3—C7—C6 | 125.15 (14) | C3—C2—H2 | 119.5 |
N1—C7—C6 | 110.07 (13) | N2—C8—C9 | 121.01 (14) |
C5—C4—H4 | 121.8 | N2—C8—H8 | 119.5 |
C5—C4—C3 | 116.40 (15) | C9—C8—H8 | 119.5 |
C3—C4—H4 | 121.8 | C6—C1—C2 | 118.22 (15) |
C9—C10—H10 | 120.5 | C6—C1—H1 | 120.9 |
C11—C10—H10 | 120.5 | C2—C1—H1 | 120.9 |
C11—C10—C9 | 119.06 (15) | C10—C11—H11 | 120.4 |
S1—N1—I1 | 116.94 (7) | C12—C11—C10 | 119.21 (15) |
C7—N1—I1 | 127.92 (10) | C12—C11—H11 | 120.4 |
C7—N1—S1 | 113.75 (11) | C4—C3—H3 | 119.3 |
N2—C12—H12 | 119.5 | C2—C3—C4 | 121.32 (15) |
N2—C12—C11 | 120.94 (15) | C2—C3—H3 | 119.3 |
C11—C12—H12 | 119.5 | | |
| | | |
I1—N2—C12—C11 | 169.89 (12) | N1—C7—C6—C1 | −179.41 (16) |
I1—N2—C8—C9 | −170.31 (12) | C12—N2—C8—C9 | 1.0 (2) |
S1—C5—C6—C7 | 2.93 (16) | C5—S1—N1—I1 | −164.71 (8) |
S1—C5—C6—C1 | −178.52 (12) | C5—S1—N1—C7 | 2.91 (13) |
N2—C12—C11—C10 | 0.7 (2) | C5—C4—C3—C2 | −0.3 (2) |
O3—C7—N1—I1 | −14.6 (2) | C5—C6—C1—C2 | −0.6 (2) |
O3—C7—N1—S1 | 179.39 (14) | O2—S1—N1—I1 | 81.58 (9) |
O3—C7—C6—C5 | 177.99 (15) | O2—S1—N1—C7 | −110.80 (12) |
O3—C7—C6—C1 | −0.4 (3) | O2—S1—C5—C4 | −67.73 (16) |
O1—S1—N1—I1 | −48.93 (10) | O2—S1—C5—C6 | 110.58 (12) |
O1—S1—N1—C7 | 118.69 (12) | C6—C7—N1—I1 | 164.36 (10) |
O1—S1—C5—C4 | 63.23 (17) | C6—C7—N1—S1 | −1.62 (17) |
O1—S1—C5—C6 | −118.46 (12) | C9—C10—C11—C12 | 0.6 (2) |
C7—C6—C1—C2 | 177.73 (15) | C8—N2—C12—C11 | −1.5 (2) |
C4—C5—C6—C7 | −178.66 (14) | C1—C2—C3—C4 | −0.4 (3) |
C4—C5—C6—C1 | −0.1 (2) | C11—C10—C9—C8 | −1.1 (2) |
C10—C9—C8—N2 | 0.4 (2) | C3—C4—C5—S1 | 178.63 (13) |
N1—S1—C5—C4 | 178.32 (15) | C3—C4—C5—C6 | 0.5 (2) |
N1—S1—C5—C6 | −3.37 (12) | C3—C2—C1—C6 | 0.8 (3) |
N1—C7—C6—C5 | −1.00 (18) | | |
NISac.Py_0GPa (dac_0.00_GPa)
top
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 1.913 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 27.291 (14) Å | Cell parameters from 3353 reflections |
b = 7.8228 (16) Å | θ = 3.0–20.9° |
c = 12.628 (3) Å | µ = 2.54 mm−1 |
β = 88.579 (11)° | T = 296 K |
V = 2695.1 (16) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 595 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.045 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0620 before and 0.0503 after correction.
The Ratio of minimum to maximum transmission is 0.8187.
The λ/2 correction factor is Not present. | θmax = 23.2°, θmin = 1.8° |
Tmin = 0.461, Tmax = 0.563 | h = −10→10 |
10351 measured reflections | k = −8→8 |
770 independent reflections | l = −14→14 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0411P)2 + 9.578P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
770 reflections | Δρmax = 0.46 e Å−3 |
71 parameters | Δρmin = −0.34 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28458 (5) | 0.39779 (7) | 0.47941 (4) | 0.0474 (9) | |
S1 | 0.40367 (19) | 0.4728 (3) | 0.44916 (15) | 0.047 (3) | |
N2 | 0.2162 (6) | 0.3857 (8) | 0.5884 (5) | 0.044 | |
O3 | 0.3277 (6) | 0.4096 (8) | 0.2142 (5) | 0.058 | |
O1 | 0.3962 (6) | 0.6150 (8) | 0.5179 (4) | 0.066 | |
C7 | 0.3607 (9) | 0.4397 (10) | 0.2769 (6) | 0.041 | |
C4 | 0.4870 (6) | 0.5916 (12) | 0.3292 (7) | 0.051 | |
H4 | 0.5053 | 0.6075 | 0.3896 | 0.061* | |
C10 | 0.1388 (7) | 0.4111 (11) | 0.7304 (7) | 0.054 | |
H10 | 0.1129 | 0.4214 | 0.7791 | 0.065* | |
N1 | 0.3546 (6) | 0.4264 (8) | 0.3848 (5) | 0.045 | |
C12 | 0.2202 (7) | 0.3237 (10) | 0.6863 (6) | 0.053 | |
H12 | 0.2492 | 0.2708 | 0.7055 | 0.063* | |
C5 | 0.4388 (6) | 0.5316 (10) | 0.3349 (6) | 0.038 | |
O2 | 0.4250 (5) | 0.3225 (8) | 0.4960 (4) | 0.061 | |
C6 | 0.4090 (7) | 0.5001 (10) | 0.2480 (5) | 0.037 | |
C9 | 0.1345 (7) | 0.4699 (11) | 0.6280 (7) | 0.053 | |
H9 | 0.1054 | 0.5191 | 0.6063 | 0.064* | |
C2 | 0.4781 (6) | 0.5980 (12) | 0.1396 (7) | 0.058 | |
H2 | 0.4917 | 0.6210 | 0.0728 | 0.070* | |
C8 | 0.1743 (6) | 0.4545 (11) | 0.5576 (6) | 0.039 | |
H8 | 0.1716 | 0.4928 | 0.4883 | 0.047* | |
C1 | 0.4301 (6) | 0.5363 (12) | 0.1474 (6) | 0.052 | |
H1 | 0.4122 | 0.5193 | 0.0866 | 0.062* | |
C11 | 0.1820 (7) | 0.3373 (11) | 0.7589 (7) | 0.052 | |
H11 | 0.1856 | 0.2964 | 0.8275 | 0.062* | |
C3 | 0.5065 (7) | 0.6263 (11) | 0.2284 (6) | 0.057 | |
H3 | 0.5382 | 0.6682 | 0.2203 | 0.068* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.050 (3) | 0.0455 (4) | 0.0462 (4) | −0.0006 (5) | 0.0027 (5) | 0.0007 (2) |
S1 | 0.048 (12) | 0.0565 (14) | 0.0359 (12) | −0.008 (2) | −0.001 (2) | 0.0011 (10) |
N2 | 0.044 | 0.044 | 0.044 | 0.000 | 0.002 | 0.001 |
O3 | 0.045 | 0.079 | 0.049 | 0.000 | 0.000 | 0.000 |
O1 | 0.068 | 0.089 | 0.041 | 0.000 | 0.002 | 0.000 |
C7 | 0.040 | 0.044 | 0.039 | 0.006 | 0.000 | 0.000 |
C4 | 0.037 | 0.060 | 0.056 | 0.000 | 0.000 | 0.000 |
C10 | 0.052 | 0.061 | 0.050 | 0.000 | 0.019 | 0.000 |
N1 | 0.041 | 0.055 | 0.039 | 0.000 | 0.000 | 0.002 |
C12 | 0.066 | 0.043 | 0.048 | 0.000 | 0.000 | 0.005 |
C5 | 0.038 | 0.037 | 0.038 | 0.000 | 0.000 | 0.000 |
O2 | 0.056 | 0.070 | 0.057 | 0.000 | 0.000 | 0.018 |
C6 | 0.027 | 0.043 | 0.040 | 0.007 | 0.000 | 0.000 |
C9 | 0.042 | 0.059 | 0.058 | 0.022 | 0.000 | 0.000 |
C2 | 0.053 | 0.065 | 0.055 | 0.005 | 0.013 | 0.006 |
C8 | 0.026 | 0.053 | 0.039 | 0.000 | 0.000 | 0.006 |
C1 | 0.047 | 0.069 | 0.039 | 0.010 | 0.000 | 0.000 |
C11 | 0.061 | 0.053 | 0.042 | 0.000 | 0.000 | 0.006 |
C3 | 0.037 | 0.057 | 0.076 | 0.000 | 0.011 | 0.004 |
Geometric parameters (Å, º) top
I1—N2 | 2.294 (13) | C10—C9 | 1.381 (11) |
I1—N1 | 2.239 (15) | C10—C11 | 1.369 (18) |
S1—O1 | 1.423 (7) | C12—H12 | 0.9300 |
S1—N1 | 1.625 (16) | C12—C11 | 1.376 (18) |
S1—C5 | 1.773 (12) | C5—C6 | 1.403 (12) |
S1—O2 | 1.445 (8) | C6—C1 | 1.411 (11) |
N2—C12 | 1.335 (9) | C9—H9 | 0.9300 |
N2—C8 | 1.329 (15) | C9—C8 | 1.391 (19) |
O3—C7 | 1.24 (2) | C2—H2 | 0.9300 |
C7—N1 | 1.374 (11) | C2—C1 | 1.397 (14) |
C7—C6 | 1.44 (3) | C2—C3 | 1.396 (12) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.398 (14) | C1—H1 | 0.9300 |
C4—C3 | 1.394 (11) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N1—I1—N2 | 174.4 (3) | C4—C5—S1 | 128.2 (7) |
O1—S1—N1 | 111.9 (8) | C4—C5—C6 | 125.5 (10) |
O1—S1—C5 | 111.1 (5) | C6—C5—S1 | 106.2 (9) |
O1—S1—O2 | 116.1 (4) | C5—C6—C7 | 113.8 (9) |
N1—S1—C5 | 95.0 (5) | C5—C6—C1 | 116.0 (12) |
O2—S1—N1 | 111.6 (5) | C1—C6—C7 | 130.2 (12) |
O2—S1—C5 | 109.2 (6) | C10—C9—H9 | 120.4 |
C12—N2—I1 | 119.0 (10) | C10—C9—C8 | 119.1 (14) |
C8—N2—I1 | 120.0 (6) | C8—C9—H9 | 120.4 |
C8—N2—C12 | 120.7 (12) | C1—C2—H2 | 118.8 |
O3—C7—N1 | 123.3 (18) | C3—C2—H2 | 118.8 |
O3—C7—C6 | 125.3 (9) | C3—C2—C1 | 122.4 (11) |
N1—C7—C6 | 111.4 (15) | N2—C8—C9 | 120.7 (10) |
C5—C4—H4 | 121.6 | N2—C8—H8 | 119.6 |
C3—C4—H4 | 121.6 | C9—C8—H8 | 119.6 |
C3—C4—C5 | 116.7 (11) | C6—C1—H1 | 120.2 |
C9—C10—H10 | 120.6 | C2—C1—C6 | 119.6 (11) |
C11—C10—H10 | 120.6 | C2—C1—H1 | 120.2 |
C11—C10—C9 | 118.7 (15) | C10—C11—C12 | 120.0 (10) |
S1—N1—I1 | 117.3 (4) | C10—C11—H11 | 120.0 |
C7—N1—I1 | 128.2 (13) | C12—C11—H11 | 120.0 |
C7—N1—S1 | 113.5 (13) | C4—C3—C2 | 119.8 (14) |
N2—C12—H12 | 119.7 | C4—C3—H3 | 120.1 |
N2—C12—C11 | 120.7 (13) | C2—C3—H3 | 120.1 |
C11—C12—H12 | 119.7 | | |
| | | |
I1—N2—C12—C11 | 170.4 (7) | N1—C7—C6—C1 | −178.0 (9) |
I1—N2—C8—C9 | −170.9 (7) | C12—N2—C8—C9 | 2.7 (15) |
S1—C5—C6—C7 | 2.4 (11) | C5—S1—N1—I1 | −165.5 (4) |
S1—C5—C6—C1 | −179.2 (8) | C5—S1—N1—C7 | 3.7 (7) |
N2—C12—C11—C10 | 1.7 (15) | C5—C4—C3—C2 | −1.0 (14) |
O3—C7—N1—I1 | −12.3 (12) | C5—C6—C1—C2 | 0.6 (14) |
O3—C7—N1—S1 | 179.9 (8) | O2—S1—N1—I1 | 81.5 (6) |
O3—C7—C6—C5 | 177.2 (9) | O2—S1—N1—C7 | −109.3 (7) |
O3—C7—C6—C1 | −1 (2) | O2—S1—C5—C4 | −66.4 (11) |
O1—S1—N1—I1 | −50.4 (5) | O2—S1—C5—C6 | 111.5 (7) |
O1—S1—N1—C7 | 118.8 (7) | C6—C7—N1—I1 | 165.0 (8) |
O1—S1—C5—C4 | 62.9 (13) | C6—C7—N1—S1 | −2.8 (12) |
O1—S1—C5—C6 | −119.2 (8) | C9—C10—C11—C12 | 0.3 (16) |
C7—C6—C1—C2 | 178.6 (13) | C8—N2—C12—C11 | −3.2 (14) |
C4—C5—C6—C7 | −179.6 (12) | C1—C2—C3—C4 | 0.4 (16) |
C4—C5—C6—C1 | −1.3 (14) | C11—C10—C9—C8 | −0.9 (16) |
C10—C9—C8—N2 | −0.6 (15) | C3—C4—C5—S1 | 179.0 (7) |
N1—S1—C5—C4 | 178.7 (10) | C3—C4—C5—C6 | 1.5 (15) |
N1—S1—C5—C6 | −3.4 (7) | C3—C2—C1—C6 | −0.2 (17) |
N1—C7—C6—C5 | 0.0 (14) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 1.912 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 27.272 (19) Å | Cell parameters from 2343 reflections |
b = 7.834 (2) Å | θ = 3.0–19.1° |
c = 12.630 (4) Å | µ = 2.53 mm−1 |
β = 88.507 (15)° | T = 296 K |
V = 2697 (2) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 545 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.069 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. | θmax = 23.2°, θmin = 1.8° |
Tmin = 0.461, Tmax = 0.563 | h = −12→11 |
8714 measured reflections | k = −8→8 |
830 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.049P)2 + 19.6592P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
830 reflections | Δρmax = 0.38 e Å−3 |
71 parameters | Δρmin = −0.51 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28457 (8) | 0.39800 (11) | 0.47952 (6) | 0.0552 (11) | |
S1 | 0.4038 (3) | 0.4724 (4) | 0.4494 (2) | 0.059 (4) | |
N2 | 0.2177 (8) | 0.3837 (13) | 0.5882 (7) | 0.051 | |
O3 | 0.3287 (7) | 0.4098 (12) | 0.2144 (7) | 0.064 | |
O1 | 0.3960 (8) | 0.6135 (12) | 0.5181 (6) | 0.071 | |
C7 | 0.3598 (12) | 0.4394 (15) | 0.2777 (10) | 0.051 | |
C4 | 0.4872 (8) | 0.5907 (18) | 0.3288 (9) | 0.057 | |
H4 | 0.5061 | 0.6036 | 0.3885 | 0.069* | |
C10 | 0.1386 (9) | 0.4135 (17) | 0.7304 (10) | 0.068 | |
H10 | 0.1129 | 0.4252 | 0.7796 | 0.081* | |
N1 | 0.3545 (9) | 0.4250 (12) | 0.3861 (7) | 0.049 | |
C12 | 0.2204 (10) | 0.3231 (16) | 0.6859 (9) | 0.069 | |
H12 | 0.2491 | 0.2697 | 0.7064 | 0.082* | |
C5 | 0.4386 (8) | 0.5342 (15) | 0.3352 (9) | 0.045 | |
O2 | 0.4252 (7) | 0.3230 (12) | 0.4959 (6) | 0.068 | |
C6 | 0.4092 (10) | 0.4984 (15) | 0.2480 (8) | 0.045 | |
C9 | 0.1336 (10) | 0.4728 (16) | 0.6290 (9) | 0.057 | |
H9 | 0.1046 | 0.5216 | 0.6064 | 0.069* | |
C2 | 0.4774 (7) | 0.5988 (17) | 0.1384 (10) | 0.060 | |
H2 | 0.4908 | 0.6228 | 0.0715 | 0.072* | |
C8 | 0.1755 (9) | 0.4547 (17) | 0.5609 (10) | 0.050 | |
H8 | 0.1733 | 0.4956 | 0.4920 | 0.060* | |
C1 | 0.4296 (8) | 0.5361 (17) | 0.1475 (9) | 0.055 | |
H1 | 0.4113 | 0.5195 | 0.0872 | 0.066* | |
C11 | 0.1810 (9) | 0.3379 (16) | 0.7591 (10) | 0.063 | |
H11 | 0.1840 | 0.2957 | 0.8275 | 0.076* | |
C3 | 0.5056 (9) | 0.6263 (16) | 0.2272 (8) | 0.064 | |
H3 | 0.5373 | 0.6692 | 0.2186 | 0.077* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.056 (4) | 0.0574 (6) | 0.0515 (5) | −0.0010 (8) | −0.0009 (7) | 0.0005 (4) |
S1 | 0.072 (14) | 0.065 (2) | 0.0395 (18) | −0.006 (3) | −0.003 (3) | −0.0004 (15) |
N2 | 0.051 | 0.050 | 0.050 | 0.000 | 0.003 | 0.001 |
O3 | 0.050 | 0.088 | 0.055 | 0.000 | 0.000 | 0.000 |
O1 | 0.073 | 0.095 | 0.045 | 0.000 | 0.002 | 0.000 |
C7 | 0.049 | 0.055 | 0.049 | 0.007 | 0.000 | 0.000 |
C4 | 0.042 | 0.068 | 0.062 | 0.000 | 0.000 | 0.000 |
C10 | 0.065 | 0.075 | 0.061 | 0.000 | 0.023 | 0.000 |
N1 | 0.044 | 0.060 | 0.042 | 0.000 | 0.000 | 0.002 |
C12 | 0.086 | 0.056 | 0.063 | 0.000 | 0.000 | 0.007 |
C5 | 0.046 | 0.044 | 0.045 | 0.000 | 0.000 | 0.000 |
O2 | 0.062 | 0.078 | 0.063 | 0.000 | 0.000 | 0.020 |
C6 | 0.033 | 0.052 | 0.048 | 0.009 | 0.000 | 0.001 |
C9 | 0.046 | 0.064 | 0.063 | 0.023 | 0.000 | 0.000 |
C2 | 0.055 | 0.068 | 0.057 | 0.005 | 0.014 | 0.007 |
C8 | 0.033 | 0.067 | 0.049 | 0.000 | 0.000 | 0.007 |
C1 | 0.049 | 0.073 | 0.041 | 0.011 | 0.000 | 0.000 |
C11 | 0.074 | 0.065 | 0.051 | 0.000 | 0.000 | 0.007 |
C3 | 0.041 | 0.064 | 0.086 | 0.000 | 0.012 | 0.005 |
Geometric parameters (Å, º) top
I1—N2 | 2.257 (18) | C10—C9 | 1.372 (15) |
I1—N1 | 2.23 (2) | C10—C11 | 1.36 (2) |
S1—O1 | 1.418 (10) | C12—H12 | 0.9300 |
S1—N1 | 1.63 (2) | C12—C11 | 1.40 (3) |
S1—C5 | 1.772 (17) | C5—C6 | 1.406 (14) |
S1—O2 | 1.440 (12) | C6—C1 | 1.404 (13) |
N2—C12 | 1.326 (13) | C9—H9 | 0.9300 |
N2—C8 | 1.331 (19) | C9—C8 | 1.42 (3) |
O3—C7 | 1.20 (3) | C2—H2 | 0.9300 |
C7—N1 | 1.377 (15) | C2—C1 | 1.396 (16) |
C7—C6 | 1.46 (4) | C2—C3 | 1.393 (14) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.399 (16) | C1—H1 | 0.9300 |
C4—C3 | 1.394 (13) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N1—I1—N2 | 174.1 (5) | C4—C5—S1 | 128.3 (10) |
O1—S1—N1 | 111.5 (11) | C4—C5—C6 | 125.1 (14) |
O1—S1—C5 | 110.7 (7) | C6—C5—S1 | 106.2 (12) |
O1—S1—O2 | 116.1 (6) | C5—C6—C7 | 113.7 (12) |
N1—S1—C5 | 95.4 (7) | C1—C6—C7 | 129.6 (16) |
O2—S1—N1 | 111.3 (7) | C1—C6—C5 | 116.6 (16) |
O2—S1—C5 | 109.9 (8) | C10—C9—H9 | 122.2 |
C12—N2—I1 | 121.3 (14) | C10—C9—C8 | 115.7 (19) |
C12—N2—C8 | 117.5 (17) | C8—C9—H9 | 122.2 |
C8—N2—I1 | 120.8 (9) | C1—C2—H2 | 119.3 |
O3—C7—N1 | 126 (2) | C3—C2—H2 | 119.3 |
O3—C7—C6 | 123.5 (14) | C3—C2—C1 | 121.5 (15) |
N1—C7—C6 | 111 (2) | N2—C8—C9 | 124.9 (15) |
C5—C4—H4 | 122.1 | N2—C8—H8 | 117.5 |
C3—C4—H4 | 122.1 | C9—C8—H8 | 117.5 |
C3—C4—C5 | 115.8 (16) | C6—C1—H1 | 120.2 |
C9—C10—H10 | 119.9 | C2—C1—C6 | 119.7 (15) |
C11—C10—H10 | 119.9 | C2—C1—H1 | 120.2 |
C11—C10—C9 | 120 (2) | C10—C11—C12 | 120.2 (15) |
S1—N1—I1 | 118.0 (5) | C10—C11—H11 | 119.9 |
C7—N1—I1 | 127.0 (18) | C12—C11—H11 | 119.9 |
C7—N1—S1 | 113.8 (18) | C4—C3—H3 | 119.4 |
N2—C12—H12 | 119.3 | C2—C3—C4 | 121.1 (18) |
N2—C12—C11 | 121.5 (19) | C2—C3—H3 | 119.4 |
C11—C12—H12 | 119.3 | | |
| | | |
I1—N2—C12—C11 | 170.1 (11) | N1—C7—C6—C1 | −177.4 (13) |
I1—N2—C8—C9 | −171.1 (12) | C12—N2—C8—C9 | 1 (2) |
S1—C5—C6—C7 | 5.2 (15) | C5—S1—N1—I1 | −164.2 (6) |
S1—C5—C6—C1 | −179.5 (11) | C5—S1—N1—C7 | 3.8 (11) |
N2—C12—C11—C10 | 1 (2) | C5—C4—C3—C2 | −3 (2) |
O3—C7—N1—I1 | −14.0 (19) | C5—C6—C1—C2 | 3 (2) |
O3—C7—N1—S1 | 179.3 (13) | O2—S1—N1—I1 | 82.0 (9) |
O3—C7—C6—C5 | 176.6 (13) | O2—S1—N1—C7 | −110.0 (10) |
O3—C7—C6—C1 | 2 (3) | O2—S1—C5—C4 | −64.0 (16) |
O1—S1—N1—I1 | −49.4 (7) | O2—S1—C5—C6 | 109.9 (11) |
O1—S1—N1—C7 | 118.6 (11) | C6—C7—N1—I1 | 165.4 (11) |
O1—S1—C5—C4 | 65.6 (18) | C6—C7—N1—S1 | −1.3 (17) |
O1—S1—C5—C6 | −120.6 (11) | C9—C10—C11—C12 | 1 (2) |
C7—C6—C1—C2 | 177.0 (17) | C8—N2—C12—C11 | −2 (2) |
C4—C5—C6—C7 | 179.3 (17) | C1—C2—C3—C4 | 1 (2) |
C4—C5—C6—C1 | −5 (2) | C11—C10—C9—C8 | −2 (2) |
C10—C9—C8—N2 | 1 (2) | C3—C4—C5—S1 | 178.3 (10) |
N1—S1—C5—C4 | −179.0 (15) | C3—C4—C5—C6 | 5 (2) |
N1—S1—C5—C6 | −5.1 (10) | C3—C2—C1—C6 | 0 (2) |
N1—C7—C6—C5 | −2.9 (19) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 1.919 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 27.246 (16) Å | Cell parameters from 2630 reflections |
b = 7.819 (2) Å | θ = 3.0–20.2° |
c = 12.621 (3) Å | µ = 2.54 mm−1 |
β = 88.538 (13)° | T = 296 K |
V = 2687.7 (19) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 583 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.063 |
Absorption correction: numerical SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0628 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.8355.
The λ/2 correction factor is Not present. | θmax = 23.3°, θmin = 1.8° |
Tmin = 0.470, Tmax = 0.563 | h = −11→11 |
10196 measured reflections | k = −8→8 |
817 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0332P)2 + 36.6993P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
817 reflections | Δρmax = 0.45 e Å−3 |
71 parameters | Δρmin = −0.37 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28447 (8) | 0.39795 (10) | 0.47948 (6) | 0.0514 (11) | |
S1 | 0.4036 (3) | 0.4727 (4) | 0.4491 (2) | 0.059 (4) | |
N2 | 0.2174 (8) | 0.3836 (13) | 0.5880 (7) | 0.051 | |
O3 | 0.3288 (7) | 0.4083 (12) | 0.2135 (7) | 0.062 | |
O1 | 0.3963 (7) | 0.6156 (12) | 0.5180 (6) | 0.070 | |
C7 | 0.3603 (11) | 0.4387 (14) | 0.2768 (9) | 0.043 | |
C4 | 0.4873 (8) | 0.5907 (18) | 0.3289 (10) | 0.057 | |
H4 | 0.5059 | 0.6041 | 0.3891 | 0.069* | |
C10 | 0.1380 (9) | 0.4143 (17) | 0.7304 (10) | 0.061 | |
H10 | 0.1120 | 0.4261 | 0.7792 | 0.073* | |
N1 | 0.3534 (9) | 0.4260 (12) | 0.3850 (7) | 0.049 | |
C12 | 0.2203 (9) | 0.3262 (15) | 0.6857 (9) | 0.059 | |
H12 | 0.2494 | 0.2757 | 0.7069 | 0.070* | |
C5 | 0.4382 (8) | 0.5344 (15) | 0.3359 (9) | 0.046 | |
O2 | 0.4251 (7) | 0.3225 (11) | 0.4959 (6) | 0.067 | |
C6 | 0.4080 (10) | 0.5017 (15) | 0.2486 (8) | 0.041 | |
C9 | 0.1336 (10) | 0.4727 (15) | 0.6289 (9) | 0.051 | |
H9 | 0.1046 | 0.5219 | 0.6060 | 0.062* | |
C2 | 0.4783 (8) | 0.5993 (18) | 0.1382 (10) | 0.063 | |
H2 | 0.4915 | 0.6223 | 0.0711 | 0.076* | |
C8 | 0.1753 (8) | 0.4546 (16) | 0.5602 (9) | 0.042 | |
H8 | 0.1731 | 0.4951 | 0.4913 | 0.051* | |
C1 | 0.4300 (8) | 0.5386 (17) | 0.1487 (9) | 0.054 | |
H1 | 0.4119 | 0.5222 | 0.0880 | 0.065* | |
C11 | 0.1806 (9) | 0.3388 (16) | 0.7592 (10) | 0.057 | |
H11 | 0.1835 | 0.2955 | 0.8273 | 0.069* | |
C3 | 0.5070 (10) | 0.6257 (16) | 0.2273 (9) | 0.065 | |
H3 | 0.5389 | 0.6663 | 0.2192 | 0.078* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.050 (4) | 0.0540 (5) | 0.0502 (5) | −0.0016 (8) | 0.0007 (7) | 0.0009 (4) |
S1 | 0.074 (15) | 0.063 (2) | 0.0388 (18) | −0.008 (3) | −0.002 (3) | 0.0017 (15) |
N2 | 0.051 | 0.050 | 0.050 | 0.000 | 0.003 | 0.001 |
O3 | 0.049 | 0.085 | 0.053 | 0.000 | 0.000 | 0.000 |
O1 | 0.072 | 0.094 | 0.044 | 0.000 | 0.002 | 0.000 |
C7 | 0.041 | 0.046 | 0.041 | 0.006 | 0.000 | 0.000 |
C4 | 0.042 | 0.068 | 0.062 | 0.000 | 0.000 | 0.000 |
C10 | 0.058 | 0.067 | 0.055 | 0.000 | 0.021 | 0.000 |
N1 | 0.044 | 0.060 | 0.042 | 0.000 | 0.000 | 0.002 |
C12 | 0.074 | 0.048 | 0.054 | 0.000 | 0.000 | 0.006 |
C5 | 0.046 | 0.045 | 0.045 | 0.000 | 0.000 | 0.000 |
O2 | 0.061 | 0.077 | 0.062 | 0.000 | 0.000 | 0.020 |
C6 | 0.031 | 0.048 | 0.045 | 0.008 | 0.000 | 0.000 |
C9 | 0.041 | 0.057 | 0.056 | 0.021 | 0.000 | 0.000 |
C2 | 0.058 | 0.071 | 0.059 | 0.005 | 0.014 | 0.007 |
C8 | 0.028 | 0.057 | 0.042 | 0.000 | 0.000 | 0.006 |
C1 | 0.049 | 0.072 | 0.041 | 0.010 | 0.000 | 0.000 |
C11 | 0.067 | 0.058 | 0.046 | 0.000 | 0.000 | 0.007 |
C3 | 0.042 | 0.066 | 0.087 | 0.000 | 0.012 | 0.005 |
Geometric parameters (Å, º) top
I1—N2 | 2.258 (18) | C10—C9 | 1.367 (15) |
I1—N1 | 2.21 (2) | C10—C11 | 1.36 (2) |
S1—O1 | 1.427 (10) | C12—H12 | 0.9300 |
S1—N1 | 1.65 (2) | C12—C11 | 1.41 (3) |
S1—C5 | 1.758 (17) | C5—C6 | 1.415 (14) |
S1—O2 | 1.445 (12) | C6—C1 | 1.412 (14) |
N2—C12 | 1.316 (13) | C9—H9 | 0.9300 |
N2—C8 | 1.330 (19) | C9—C8 | 1.42 (3) |
O3—C7 | 1.21 (3) | C2—H2 | 0.9300 |
C7—N1 | 1.377 (15) | C2—C1 | 1.402 (16) |
C7—C6 | 1.42 (4) | C2—C3 | 1.400 (14) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.409 (16) | C1—H1 | 0.9300 |
C4—C3 | 1.404 (14) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N1—I1—N2 | 174.6 (5) | C4—C5—S1 | 128.6 (10) |
O1—S1—N1 | 111.5 (10) | C4—C5—C6 | 125.3 (14) |
O1—S1—C5 | 110.2 (7) | C6—C5—S1 | 105.9 (12) |
O1—S1—O2 | 116.1 (6) | C5—C6—C7 | 114.3 (12) |
N1—S1—C5 | 95.5 (7) | C1—C6—C7 | 131.1 (16) |
O2—S1—N1 | 111.7 (7) | C1—C6—C5 | 114.5 (16) |
O2—S1—C5 | 110.0 (8) | C10—C9—H9 | 121.6 |
C12—N2—I1 | 121.3 (14) | C10—C9—C8 | 116.8 (19) |
C12—N2—C8 | 117.5 (17) | C8—C9—H9 | 121.6 |
C8—N2—I1 | 120.6 (9) | C1—C2—H2 | 119.5 |
O3—C7—N1 | 124 (2) | C3—C2—H2 | 119.5 |
O3—C7—C6 | 124.0 (13) | C3—C2—C1 | 121.0 (15) |
N1—C7—C6 | 112 (2) | N2—C8—C9 | 124.3 (14) |
C5—C4—H4 | 121.4 | N2—C8—H8 | 117.8 |
C3—C4—H4 | 121.4 | C9—C8—H8 | 117.8 |
C3—C4—C5 | 117.3 (16) | C6—C1—H1 | 119.0 |
C9—C10—H10 | 120.3 | C2—C1—C6 | 122.0 (15) |
C11—C10—H10 | 120.3 | C2—C1—H1 | 119.0 |
C11—C10—C9 | 119 (2) | C10—C11—C12 | 120.0 (15) |
S1—N1—I1 | 117.5 (5) | C10—C11—H11 | 120.0 |
C7—N1—I1 | 129.5 (18) | C12—C11—H11 | 120.0 |
C7—N1—S1 | 112.0 (18) | C4—C3—H3 | 120.1 |
N2—C12—H12 | 119.0 | C2—C3—C4 | 119.8 (18) |
N2—C12—C11 | 121.9 (18) | C2—C3—H3 | 120.1 |
C11—C12—H12 | 119.0 | | |
| | | |
I1—N2—C12—C11 | 170.8 (10) | N1—C7—C6—C1 | −178.1 (13) |
I1—N2—C8—C9 | −170.8 (11) | C12—N2—C8—C9 | 0 (2) |
S1—C5—C6—C7 | 2.4 (15) | C5—S1—N1—I1 | −164.7 (6) |
S1—C5—C6—C1 | −178.2 (11) | C5—S1—N1—C7 | 5.2 (10) |
N2—C12—C11—C10 | −1 (2) | C5—C4—C3—C2 | −2 (2) |
O3—C7—N1—I1 | −12.6 (19) | C5—C6—C1—C2 | 1 (2) |
O3—C7—N1—S1 | 179.0 (12) | O2—S1—N1—I1 | 81.3 (9) |
O3—C7—C6—C5 | 177.6 (13) | O2—S1—N1—C7 | −108.8 (10) |
O3—C7—C6—C1 | −2 (3) | O2—S1—C5—C4 | −63.6 (16) |
O1—S1—N1—I1 | −50.5 (7) | O2—S1—C5—C6 | 111.2 (10) |
O1—S1—N1—C7 | 119.5 (10) | C6—C7—N1—I1 | 163.8 (12) |
O1—S1—C5—C4 | 65.6 (17) | C6—C7—N1—S1 | −4.6 (17) |
O1—S1—C5—C6 | −119.6 (11) | C9—C10—C11—C12 | 2 (2) |
C7—C6—C1—C2 | −179.4 (19) | C8—N2—C12—C11 | 0 (2) |
C4—C5—C6—C7 | 177.4 (17) | C1—C2—C3—C4 | 0 (2) |
C4—C5—C6—C1 | −3 (2) | C11—C10—C9—C8 | −2 (2) |
C10—C9—C8—N2 | 1 (2) | C3—C4—C5—S1 | 177.4 (10) |
N1—S1—C5—C4 | −179.1 (15) | C3—C4—C5—C6 | 4 (2) |
N1—S1—C5—C6 | −4.3 (10) | C3—C2—C1—C6 | 0 (2) |
N1—C7—C6—C5 | 1 (2) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 1.946 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 27.185 (16) Å | Cell parameters from 2886 reflections |
b = 7.7444 (19) Å | θ = 3.0–24.9° |
c = 12.593 (3) Å | µ = 2.58 mm−1 |
β = 88.608 (12)° | T = 296 K |
V = 2650.4 (18) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 564 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.071 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. | θmax = 23.3°, θmin = 1.8° |
Tmin = 0.461, Tmax = 0.563 | h = −11→10 |
9901 measured reflections | k = −8→8 |
777 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0489P)2 + 9.4112P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
777 reflections | Δρmax = 0.39 e Å−3 |
71 parameters | Δρmin = −0.47 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28389 (6) | 0.39775 (8) | 0.47914 (5) | 0.0428 (10) | |
S1 | 0.4038 (2) | 0.4736 (4) | 0.44931 (18) | 0.053 (4) | |
N2 | 0.2167 (7) | 0.3847 (10) | 0.5880 (6) | 0.041 | |
O3 | 0.3277 (7) | 0.4079 (10) | 0.2125 (6) | 0.055 | |
O1 | 0.3969 (6) | 0.6194 (9) | 0.5183 (5) | 0.059 | |
C7 | 0.3592 (11) | 0.4386 (13) | 0.2760 (8) | 0.042 | |
C4 | 0.4876 (7) | 0.5929 (15) | 0.3293 (8) | 0.050 | |
H4 | 0.5062 | 0.6077 | 0.3896 | 0.060* | |
C10 | 0.1383 (8) | 0.4145 (14) | 0.7309 (8) | 0.052 | |
H10 | 0.1123 | 0.4259 | 0.7798 | 0.062* | |
N1 | 0.3538 (8) | 0.4256 (10) | 0.3840 (6) | 0.042 | |
C12 | 0.2198 (8) | 0.3241 (13) | 0.6871 (7) | 0.052 | |
H12 | 0.2488 | 0.2710 | 0.7074 | 0.063* | |
C5 | 0.4390 (7) | 0.5355 (12) | 0.3351 (7) | 0.035 | |
O2 | 0.4243 (6) | 0.3217 (10) | 0.4973 (5) | 0.057 | |
C6 | 0.4093 (8) | 0.5010 (13) | 0.2479 (7) | 0.035 | |
C9 | 0.1338 (9) | 0.4742 (14) | 0.6283 (8) | 0.050 | |
H9 | 0.1048 | 0.5249 | 0.6065 | 0.060* | |
C2 | 0.4786 (7) | 0.6011 (15) | 0.1380 (9) | 0.057 | |
H2 | 0.4919 | 0.6266 | 0.0711 | 0.068* | |
C8 | 0.1737 (7) | 0.4567 (13) | 0.5589 (8) | 0.037 | |
H8 | 0.1709 | 0.4960 | 0.4895 | 0.044* | |
C1 | 0.4306 (7) | 0.5375 (14) | 0.1477 (7) | 0.045 | |
H1 | 0.4126 | 0.5190 | 0.0870 | 0.054* | |
C11 | 0.1816 (8) | 0.3379 (13) | 0.7599 (8) | 0.049 | |
H11 | 0.1850 | 0.2956 | 0.8285 | 0.058* | |
C3 | 0.5065 (8) | 0.6266 (13) | 0.2275 (7) | 0.053 | |
H3 | 0.5386 | 0.6671 | 0.2194 | 0.064* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.041 (3) | 0.0432 (5) | 0.0438 (5) | −0.0012 (6) | 0.0021 (6) | 0.0009 (3) |
S1 | 0.075 (14) | 0.0527 (18) | 0.0316 (14) | −0.008 (3) | −0.002 (2) | 0.0029 (13) |
N2 | 0.041 | 0.040 | 0.040 | 0.000 | 0.002 | 0.001 |
O3 | 0.043 | 0.075 | 0.047 | 0.000 | 0.000 | 0.000 |
O1 | 0.061 | 0.079 | 0.037 | 0.000 | 0.002 | 0.000 |
C7 | 0.040 | 0.045 | 0.040 | 0.006 | 0.000 | 0.000 |
C4 | 0.036 | 0.059 | 0.054 | 0.000 | 0.000 | 0.000 |
C10 | 0.050 | 0.058 | 0.047 | 0.000 | 0.018 | 0.000 |
N1 | 0.038 | 0.051 | 0.036 | 0.000 | 0.000 | 0.002 |
C12 | 0.066 | 0.043 | 0.048 | 0.000 | 0.000 | 0.005 |
C5 | 0.036 | 0.034 | 0.035 | 0.000 | 0.000 | 0.000 |
O2 | 0.052 | 0.066 | 0.054 | 0.000 | 0.000 | 0.017 |
C6 | 0.026 | 0.041 | 0.038 | 0.007 | 0.000 | 0.000 |
C9 | 0.040 | 0.055 | 0.054 | 0.020 | 0.000 | 0.000 |
C2 | 0.052 | 0.064 | 0.054 | 0.005 | 0.013 | 0.006 |
C8 | 0.025 | 0.049 | 0.037 | 0.000 | 0.000 | 0.005 |
C1 | 0.041 | 0.060 | 0.034 | 0.009 | 0.000 | 0.000 |
C11 | 0.057 | 0.050 | 0.039 | 0.000 | 0.000 | 0.006 |
C3 | 0.034 | 0.054 | 0.072 | 0.000 | 0.010 | 0.004 |
Geometric parameters (Å, º) top
I1—N2 | 2.260 (15) | C10—C9 | 1.380 (13) |
I1—N1 | 2.231 (18) | C10—C11 | 1.38 (2) |
S1—O1 | 1.434 (8) | C12—H12 | 0.9300 |
S1—N1 | 1.649 (19) | C12—C11 | 1.37 (2) |
S1—C5 | 1.774 (14) | C5—C6 | 1.404 (13) |
S1—O2 | 1.441 (10) | C6—C1 | 1.405 (12) |
N2—C12 | 1.338 (11) | C9—H9 | 0.9300 |
N2—C8 | 1.353 (17) | C9—C8 | 1.38 (2) |
O3—C7 | 1.21 (2) | C2—H2 | 0.9300 |
C7—N1 | 1.368 (13) | C2—C1 | 1.396 (15) |
C7—C6 | 1.48 (3) | C2—C3 | 1.389 (13) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.395 (15) | C1—H1 | 0.9300 |
C4—C3 | 1.394 (12) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N1—I1—N2 | 174.4 (4) | C4—C5—S1 | 128.3 (8) |
O1—S1—N1 | 112.5 (9) | C4—C5—C6 | 125.6 (12) |
O1—S1—C5 | 109.8 (6) | C6—C5—S1 | 105.9 (10) |
O1—S1—O2 | 115.8 (5) | C5—C6—C7 | 114.8 (10) |
N1—S1—C5 | 95.2 (6) | C5—C6—C1 | 115.5 (14) |
O2—S1—N1 | 110.9 (6) | C1—C6—C7 | 129.6 (14) |
O2—S1—C5 | 110.7 (7) | C10—C9—H9 | 120.9 |
C12—N2—I1 | 120.9 (12) | C10—C9—C8 | 118.3 (17) |
C12—N2—C8 | 118.2 (14) | C8—C9—H9 | 120.9 |
C8—N2—I1 | 120.5 (8) | C1—C2—H2 | 119.8 |
O3—C7—N1 | 126 (2) | C3—C2—H2 | 119.8 |
O3—C7—C6 | 124.6 (12) | C3—C2—C1 | 120.5 (13) |
N1—C7—C6 | 109.7 (18) | N2—C8—C9 | 122.5 (12) |
C5—C4—H4 | 122.1 | N2—C8—H8 | 118.8 |
C3—C4—H4 | 122.1 | C9—C8—H8 | 118.8 |
C3—C4—C5 | 115.8 (14) | C6—C1—H1 | 119.5 |
C9—C10—H10 | 120.4 | C2—C1—C6 | 121.0 (13) |
C11—C10—H10 | 120.4 | C2—C1—H1 | 119.5 |
C11—C10—C9 | 119.3 (18) | C10—C11—H11 | 120.2 |
S1—N1—I1 | 117.1 (5) | C12—C11—C10 | 119.6 (12) |
C7—N1—I1 | 127.6 (16) | C12—C11—H11 | 120.2 |
C7—N1—S1 | 114.2 (16) | C4—C3—H3 | 119.3 |
N2—C12—H12 | 118.9 | C2—C3—C4 | 121.5 (16) |
N2—C12—C11 | 122.1 (16) | C2—C3—H3 | 119.3 |
C11—C12—H12 | 118.9 | | |
| | | |
I1—N2—C12—C11 | 170.2 (9) | N1—C7—C6—C1 | −178.2 (11) |
I1—N2—C8—C9 | −170.4 (9) | C12—N2—C8—C9 | 1.9 (18) |
S1—C5—C6—C7 | 3.9 (13) | C5—S1—N1—I1 | −164.7 (5) |
S1—C5—C6—C1 | −178.7 (9) | C5—S1—N1—C7 | 4.2 (9) |
N2—C12—C11—C10 | 0.7 (18) | C5—C4—C3—C2 | −1.1 (17) |
O3—C7—N1—I1 | −13.4 (16) | C5—C6—C1—C2 | 1.0 (17) |
O3—C7—N1—S1 | 179.1 (11) | O2—S1—N1—I1 | 80.7 (7) |
O3—C7—C6—C5 | 177.3 (11) | O2—S1—N1—C7 | −110.4 (9) |
O3—C7—C6—C1 | 0 (2) | O2—S1—C5—C4 | −64.7 (13) |
O1—S1—N1—I1 | −50.8 (6) | O2—S1—C5—C6 | 110.3 (9) |
O1—S1—N1—C7 | 118.1 (9) | C6—C7—N1—I1 | 165.0 (9) |
O1—S1—C5—C4 | 64.4 (15) | C6—C7—N1—S1 | −2.5 (14) |
O1—S1—C5—C6 | −120.7 (10) | C9—C10—C11—C12 | 0.9 (19) |
C7—C6—C1—C2 | 178.0 (15) | C8—N2—C12—C11 | −2.0 (17) |
C4—C5—C6—C7 | 179.0 (14) | C1—C2—C3—C4 | −1.2 (19) |
C4—C5—C6—C1 | −3.6 (17) | C11—C10—C9—C8 | −1.0 (19) |
C10—C9—C8—N2 | −0.4 (18) | C3—C4—C5—S1 | 177.7 (8) |
N1—S1—C5—C4 | −179.5 (12) | C3—C4—C5—C6 | 3.6 (18) |
N1—S1—C5—C6 | −4.5 (8) | C3—C2—C1—C6 | 1 (2) |
N1—C7—C6—C5 | −1.2 (17) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 1.981 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 27.108 (16) Å | Cell parameters from 2326 reflections |
b = 7.6595 (19) Å | θ = 3.1–20.6° |
c = 12.539 (3) Å | µ = 2.63 mm−1 |
β = 88.662 (13)° | T = 296 K |
V = 2602.9 (18) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 536 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.080 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. | θmax = 23.2°, θmin = 1.8° |
Tmin = 0.461, Tmax = 0.563 | h = −11→10 |
8139 measured reflections | k = −8→8 |
761 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0536P)2 + 2.7067P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
761 reflections | Δρmax = 0.51 e Å−3 |
71 parameters | Δρmin = −0.48 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28317 (7) | 0.39782 (10) | 0.47885 (6) | 0.0406 (12) | |
S1 | 0.4032 (3) | 0.4752 (4) | 0.4497 (2) | 0.048 (5) | |
N2 | 0.2161 (8) | 0.3857 (12) | 0.5884 (7) | 0.041 | |
O3 | 0.3284 (8) | 0.4079 (11) | 0.2107 (7) | 0.051 | |
O1 | 0.3956 (8) | 0.6223 (10) | 0.5182 (6) | 0.054 | |
C7 | 0.3578 (12) | 0.4379 (14) | 0.2754 (9) | 0.036 | |
C4 | 0.4884 (8) | 0.5948 (16) | 0.3313 (9) | 0.043 | |
H4 | 0.5068 | 0.6105 | 0.3922 | 0.052* | |
C10 | 0.1371 (9) | 0.4141 (15) | 0.7319 (9) | 0.046 | |
H10 | 0.1109 | 0.4230 | 0.7807 | 0.055* | |
N1 | 0.3521 (9) | 0.4266 (11) | 0.3831 (7) | 0.038 | |
C12 | 0.2196 (9) | 0.3239 (14) | 0.6886 (8) | 0.045 | |
H12 | 0.2486 | 0.2694 | 0.7085 | 0.053* | |
C5 | 0.4392 (8) | 0.5349 (14) | 0.3351 (8) | 0.031 | |
O2 | 0.4235 (7) | 0.3218 (11) | 0.4984 (6) | 0.050 | |
C6 | 0.4084 (10) | 0.5003 (15) | 0.2477 (7) | 0.032 | |
C9 | 0.1320 (9) | 0.4758 (16) | 0.6284 (9) | 0.045 | |
H9 | 0.1029 | 0.5274 | 0.6066 | 0.054* | |
C2 | 0.4788 (7) | 0.5984 (15) | 0.1380 (9) | 0.042 | |
H2 | 0.4925 | 0.6201 | 0.0705 | 0.050* | |
C8 | 0.1725 (8) | 0.4568 (15) | 0.5588 (9) | 0.035 | |
H8 | 0.1696 | 0.4946 | 0.4888 | 0.043* | |
C1 | 0.4300 (8) | 0.5361 (17) | 0.1472 (9) | 0.047 | |
H1 | 0.4120 | 0.5183 | 0.0860 | 0.057* | |
C11 | 0.1812 (9) | 0.3394 (15) | 0.7624 (9) | 0.045 | |
H11 | 0.1849 | 0.3001 | 0.8319 | 0.054* | |
C3 | 0.5074 (10) | 0.6289 (15) | 0.2281 (8) | 0.052 | |
H3 | 0.5393 | 0.6720 | 0.2194 | 0.062* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.041 (4) | 0.0395 (5) | 0.0410 (5) | −0.0010 (7) | 0.0028 (7) | 0.0009 (4) |
S1 | 0.069 (16) | 0.046 (2) | 0.0300 (17) | −0.002 (3) | −0.001 (3) | 0.0007 (14) |
N2 | 0.041 | 0.040 | 0.040 | 0.000 | 0.002 | 0.001 |
O3 | 0.040 | 0.070 | 0.044 | 0.000 | 0.000 | 0.000 |
O1 | 0.056 | 0.073 | 0.034 | 0.000 | 0.001 | 0.000 |
C7 | 0.035 | 0.039 | 0.035 | 0.005 | 0.000 | 0.000 |
C4 | 0.032 | 0.051 | 0.047 | 0.000 | 0.000 | 0.000 |
C10 | 0.044 | 0.051 | 0.042 | 0.000 | 0.016 | 0.000 |
N1 | 0.035 | 0.047 | 0.033 | 0.000 | 0.000 | 0.002 |
C12 | 0.056 | 0.036 | 0.041 | 0.000 | 0.000 | 0.005 |
C5 | 0.032 | 0.031 | 0.031 | 0.000 | 0.000 | 0.000 |
O2 | 0.046 | 0.058 | 0.047 | 0.000 | 0.000 | 0.015 |
C6 | 0.024 | 0.037 | 0.035 | 0.006 | 0.000 | 0.000 |
C9 | 0.036 | 0.050 | 0.049 | 0.018 | 0.000 | 0.000 |
C2 | 0.039 | 0.047 | 0.040 | 0.003 | 0.010 | 0.005 |
C8 | 0.024 | 0.047 | 0.035 | 0.000 | 0.000 | 0.005 |
C1 | 0.043 | 0.063 | 0.036 | 0.009 | 0.000 | 0.000 |
C11 | 0.053 | 0.046 | 0.036 | 0.000 | 0.000 | 0.005 |
C3 | 0.033 | 0.052 | 0.070 | 0.000 | 0.010 | 0.004 |
Geometric parameters (Å, º) top
I1—N2 | 2.256 (18) | C10—C9 | 1.391 (15) |
I1—N1 | 2.21 (2) | C10—C11 | 1.39 (2) |
S1—O1 | 1.429 (9) | C12—H12 | 0.9300 |
S1—N1 | 1.68 (2) | C12—C11 | 1.38 (2) |
S1—C5 | 1.778 (16) | C5—C6 | 1.419 (15) |
S1—O2 | 1.439 (11) | C6—C1 | 1.404 (13) |
N2—C12 | 1.348 (13) | C9—H9 | 0.9300 |
N2—C8 | 1.360 (19) | C9—C8 | 1.39 (2) |
O3—C7 | 1.17 (3) | C2—H2 | 0.9300 |
C7—N1 | 1.358 (15) | C2—C1 | 1.408 (16) |
C7—C6 | 1.49 (4) | C2—C3 | 1.404 (15) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.409 (16) | C1—H1 | 0.9300 |
C4—C3 | 1.407 (13) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N1—I1—N2 | 174.5 (5) | C4—C5—S1 | 127.7 (9) |
O1—S1—N1 | 111.4 (10) | C4—C5—C6 | 127.5 (14) |
O1—S1—C5 | 110.6 (6) | C6—C5—S1 | 104.7 (11) |
O1—S1—O2 | 116.1 (6) | C5—C6—C7 | 115.9 (12) |
N1—S1—C5 | 95.7 (7) | C1—C6—C7 | 129.6 (15) |
O2—S1—N1 | 111.0 (7) | C1—C6—C5 | 114.5 (16) |
O2—S1—C5 | 110.2 (8) | C10—C9—H9 | 121.5 |
C12—N2—I1 | 120.6 (14) | C10—C9—C8 | 117.1 (18) |
C12—N2—C8 | 118.4 (16) | C8—C9—H9 | 121.5 |
C8—N2—I1 | 120.7 (9) | C1—C2—H2 | 119.1 |
O3—C7—N1 | 128 (3) | C3—C2—H2 | 119.1 |
O3—C7—C6 | 122.6 (14) | C3—C2—C1 | 121.7 (14) |
N1—C7—C6 | 110 (2) | N2—C8—C9 | 123.2 (14) |
C5—C4—H4 | 122.6 | N2—C8—H8 | 118.4 |
C3—C4—H4 | 122.6 | C9—C8—H8 | 118.4 |
C3—C4—C5 | 114.7 (15) | C6—C1—C2 | 120.8 (14) |
C9—C10—H10 | 119.9 | C6—C1—H1 | 119.6 |
C11—C10—H10 | 119.9 | C2—C1—H1 | 119.6 |
C11—C10—C9 | 120.1 (19) | C10—C11—H11 | 120.3 |
S1—N1—I1 | 116.7 (5) | C12—C11—C10 | 119.4 (14) |
C7—N1—I1 | 128.5 (19) | C12—C11—H11 | 120.3 |
C7—N1—S1 | 113.9 (19) | C4—C3—H3 | 119.6 |
N2—C12—H12 | 119.1 | C2—C3—C4 | 120.8 (18) |
N2—C12—C11 | 121.7 (17) | C2—C3—H3 | 119.6 |
C11—C12—H12 | 119.1 | | |
| | | |
I1—N2—C12—C11 | 169.9 (10) | N1—C7—C6—C1 | −177.9 (12) |
I1—N2—C8—C9 | −170.4 (11) | C12—N2—C8—C9 | 3 (2) |
S1—C5—C6—C7 | 2.9 (15) | C5—S1—N1—I1 | −166.0 (6) |
S1—C5—C6—C1 | −179.0 (10) | C5—S1—N1—C7 | 4.1 (10) |
N2—C12—C11—C10 | 3 (2) | C5—C4—C3—C2 | −1.9 (18) |
O3—C7—N1—I1 | −12.9 (19) | C5—C6—C1—C2 | 0.9 (19) |
O3—C7—N1—S1 | 178.4 (13) | O2—S1—N1—I1 | 79.9 (8) |
O3—C7—C6—C5 | 178.5 (13) | O2—S1—N1—C7 | −110.1 (10) |
O3—C7—C6—C1 | 1 (3) | O2—S1—C5—C4 | −66.1 (15) |
O1—S1—N1—I1 | −51.2 (7) | O2—S1—C5—C6 | 111.0 (10) |
O1—S1—N1—C7 | 118.8 (10) | C6—C7—N1—I1 | 165.8 (11) |
O1—S1—C5—C4 | 63.7 (17) | C6—C7—N1—S1 | −2.8 (16) |
O1—S1—C5—C6 | −119.3 (11) | C9—C10—C11—C12 | −1 (2) |
C7—C6—C1—C2 | 178.6 (16) | C8—N2—C12—C11 | −3 (2) |
C4—C5—C6—C7 | −180.0 (16) | C1—C2—C3—C4 | 1 (2) |
C4—C5—C6—C1 | −2.0 (19) | C11—C10—C9—C8 | 1 (2) |
C10—C9—C8—N2 | −2 (2) | C3—C4—C5—S1 | 178.9 (10) |
N1—S1—C5—C4 | 179.1 (14) | C3—C4—C5—C6 | 2 (2) |
N1—S1—C5—C6 | −3.8 (9) | C3—C2—C1—C6 | −1 (2) |
N1—C7—C6—C5 | −0.3 (19) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 2.017 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.998 (13) Å | Cell parameters from 3214 reflections |
b = 7.5869 (15) Å | θ = 3.1–21.7° |
c = 12.485 (3) Å | µ = 2.67 mm−1 |
β = 88.802 (11)° | T = 296 K |
V = 2556.7 (14) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 577 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.054 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0782 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.8106.
The λ/2 correction factor is Not present. | θmax = 23.3°, θmin = 1.8° |
Tmin = 0.456, Tmax = 0.563 | h = −10→10 |
9824 measured reflections | k = −8→8 |
738 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0402P)2 + 16.5567P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
738 reflections | Δρmax = 0.53 e Å−3 |
71 parameters | Δρmin = −0.43 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28274 (6) | 0.39800 (8) | 0.47855 (5) | 0.0367 (10) | |
S1 | 0.4030 (2) | 0.4765 (3) | 0.44981 (18) | 0.033 (4) | |
N2 | 0.2164 (7) | 0.3857 (11) | 0.5885 (6) | 0.037 | |
O3 | 0.3285 (7) | 0.4064 (9) | 0.2090 (6) | 0.044 | |
O1 | 0.3946 (7) | 0.6256 (9) | 0.5178 (5) | 0.053 | |
C7 | 0.3599 (10) | 0.4383 (12) | 0.2735 (8) | 0.030 | |
C4 | 0.4878 (7) | 0.5960 (15) | 0.3317 (8) | 0.045 | |
H4 | 0.5062 | 0.6110 | 0.3932 | 0.054* | |
C10 | 0.1370 (8) | 0.4156 (13) | 0.7340 (8) | 0.043 | |
H10 | 0.1110 | 0.4248 | 0.7837 | 0.052* | |
N1 | 0.3520 (8) | 0.4262 (10) | 0.3821 (6) | 0.035 | |
C12 | 0.2208 (8) | 0.3260 (12) | 0.6898 (7) | 0.042 | |
H12 | 0.2504 | 0.2751 | 0.7106 | 0.051* | |
C5 | 0.4386 (7) | 0.5386 (12) | 0.3356 (7) | 0.027 | |
O2 | 0.4225 (6) | 0.3218 (9) | 0.4993 (5) | 0.048 | |
C6 | 0.4086 (9) | 0.5023 (13) | 0.2468 (7) | 0.032 | |
C9 | 0.1317 (8) | 0.4783 (13) | 0.6286 (7) | 0.037 | |
H9 | 0.1027 | 0.5322 | 0.6069 | 0.045* | |
C2 | 0.4800 (7) | 0.5996 (15) | 0.1379 (8) | 0.045 | |
H2 | 0.4940 | 0.6218 | 0.0706 | 0.054* | |
C8 | 0.1718 (7) | 0.4559 (13) | 0.5590 (8) | 0.031 | |
H8 | 0.1683 | 0.4904 | 0.4881 | 0.037* | |
C1 | 0.4311 (7) | 0.5364 (14) | 0.1461 (7) | 0.039 | |
H1 | 0.4134 | 0.5169 | 0.0842 | 0.047* | |
C11 | 0.1819 (8) | 0.3396 (13) | 0.7624 (8) | 0.042 | |
H11 | 0.1857 | 0.2973 | 0.8317 | 0.050* | |
C3 | 0.5076 (9) | 0.6294 (13) | 0.2292 (7) | 0.046 | |
H3 | 0.5397 | 0.6722 | 0.2219 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.037 (3) | 0.0360 (4) | 0.0374 (4) | −0.0011 (6) | 0.0028 (6) | 0.0012 (3) |
S1 | 0.028 (13) | 0.0433 (16) | 0.0279 (14) | −0.003 (2) | 0.003 (2) | 0.0009 (11) |
N2 | 0.037 | 0.037 | 0.037 | 0.000 | 0.002 | 0.001 |
O3 | 0.035 | 0.061 | 0.038 | 0.000 | 0.000 | 0.000 |
O1 | 0.054 | 0.070 | 0.033 | 0.000 | 0.001 | 0.000 |
C7 | 0.029 | 0.032 | 0.028 | 0.004 | 0.000 | 0.000 |
C4 | 0.033 | 0.053 | 0.049 | 0.000 | 0.000 | 0.000 |
C10 | 0.042 | 0.048 | 0.040 | 0.000 | 0.015 | 0.000 |
N1 | 0.031 | 0.043 | 0.030 | 0.000 | 0.000 | 0.002 |
C12 | 0.053 | 0.035 | 0.039 | 0.000 | 0.000 | 0.004 |
C5 | 0.028 | 0.027 | 0.027 | 0.000 | 0.000 | 0.000 |
O2 | 0.044 | 0.055 | 0.045 | 0.000 | 0.000 | 0.014 |
C6 | 0.023 | 0.037 | 0.034 | 0.006 | 0.000 | 0.000 |
C9 | 0.030 | 0.041 | 0.041 | 0.015 | 0.000 | 0.000 |
C2 | 0.042 | 0.051 | 0.043 | 0.004 | 0.010 | 0.005 |
C8 | 0.021 | 0.042 | 0.031 | 0.000 | 0.000 | 0.004 |
C1 | 0.035 | 0.052 | 0.030 | 0.008 | 0.000 | 0.000 |
C11 | 0.049 | 0.043 | 0.034 | 0.000 | 0.000 | 0.005 |
C3 | 0.030 | 0.047 | 0.062 | 0.000 | 0.009 | 0.003 |
Geometric parameters (Å, º) top
I1—N2 | 2.235 (15) | C10—C9 | 1.408 (13) |
I1—N1 | 2.214 (18) | C10—C11 | 1.396 (19) |
S1—O1 | 1.430 (8) | C12—H12 | 0.9300 |
S1—N1 | 1.673 (19) | C12—C11 | 1.38 (2) |
S1—C5 | 1.767 (14) | C5—C6 | 1.415 (14) |
S1—O2 | 1.432 (10) | C6—C1 | 1.409 (12) |
N2—C12 | 1.350 (12) | C9—H9 | 0.9300 |
N2—C8 | 1.375 (18) | C9—C8 | 1.38 (2) |
O3—C7 | 1.21 (2) | C2—H2 | 0.9300 |
C7—N1 | 1.371 (13) | C2—C1 | 1.405 (15) |
C7—C6 | 1.43 (3) | C2—C3 | 1.394 (14) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.399 (15) | C1—H1 | 0.9300 |
C4—C3 | 1.399 (12) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N1—I1—N2 | 174.3 (4) | C4—C5—S1 | 127.7 (8) |
O1—S1—N1 | 111.0 (9) | C4—C5—C6 | 126.4 (12) |
O1—S1—C5 | 110.2 (5) | C6—C5—S1 | 105.6 (10) |
O1—S1—O2 | 116.6 (5) | C5—C6—C7 | 114.9 (11) |
N1—S1—C5 | 95.3 (6) | C1—C6—C7 | 130.3 (14) |
O2—S1—N1 | 110.2 (7) | C1—C6—C5 | 114.8 (14) |
O2—S1—C5 | 111.6 (7) | C10—C9—H9 | 121.5 |
C12—N2—I1 | 120.3 (12) | C8—C9—C10 | 116.9 (16) |
C12—N2—C8 | 118.3 (14) | C8—C9—H9 | 121.5 |
C8—N2—I1 | 121.0 (7) | C1—C2—H2 | 119.6 |
O3—C7—N1 | 123 (2) | C3—C2—H2 | 119.6 |
O3—C7—C6 | 124.5 (11) | C3—C2—C1 | 120.8 (13) |
N1—C7—C6 | 112.0 (17) | N2—C8—C9 | 123.9 (12) |
C5—C4—H4 | 122.2 | N2—C8—H8 | 118.1 |
C5—C4—C3 | 115.6 (14) | C9—C8—H8 | 118.1 |
C3—C4—H4 | 122.2 | C6—C1—H1 | 119.5 |
C9—C10—H10 | 120.6 | C2—C1—C6 | 121.0 (13) |
C11—C10—H10 | 120.6 | C2—C1—H1 | 119.5 |
C11—C10—C9 | 118.8 (17) | C10—C11—H11 | 119.4 |
S1—N1—I1 | 116.2 (4) | C12—C11—C10 | 121.2 (12) |
C7—N1—I1 | 131.0 (16) | C12—C11—H11 | 119.4 |
C7—N1—S1 | 111.9 (16) | C4—C3—H3 | 119.4 |
N2—C12—H12 | 119.6 | C2—C3—C4 | 121.2 (16) |
N2—C12—C11 | 120.8 (15) | C2—C3—H3 | 119.4 |
C11—C12—H12 | 119.6 | | |
| | | |
I1—N2—C12—C11 | 171.3 (8) | N1—C7—C6—C1 | −178.9 (11) |
I1—N2—C8—C9 | −169.2 (9) | C12—N2—C8—C9 | 3.8 (17) |
S1—C5—C6—C7 | 3.0 (13) | C5—S1—N1—I1 | −165.1 (5) |
S1—C5—C6—C1 | −177.6 (9) | C5—S1—N1—C7 | 5.0 (9) |
N2—C12—C11—C10 | −0.2 (18) | C5—C4—C3—C2 | −2.5 (17) |
O3—C7—N1—I1 | −12.6 (15) | C5—C6—C1—C2 | 0.7 (17) |
O3—C7—N1—S1 | 179.2 (10) | O2—S1—N1—I1 | 79.6 (7) |
O3—C7—C6—C5 | 177.2 (11) | O2—S1—N1—C7 | −110.3 (8) |
O3—C7—C6—C1 | −2 (2) | O2—S1—C5—C4 | −64.8 (13) |
O1—S1—N1—I1 | −51.1 (6) | O2—S1—C5—C6 | 109.7 (9) |
O1—S1—N1—C7 | 119.0 (8) | C6—C7—N1—I1 | 164.2 (10) |
O1—S1—C5—C4 | 66.3 (14) | C6—C7—N1—S1 | −4.0 (14) |
O1—S1—C5—C6 | −119.1 (10) | C9—C10—C11—C12 | 0.3 (18) |
C7—C6—C1—C2 | −180.0 (15) | C8—N2—C12—C11 | −1.7 (17) |
C4—C5—C6—C7 | 177.6 (14) | C1—C2—C3—C4 | 0.6 (18) |
C4—C5—C6—C1 | −3.0 (17) | C11—C10—C9—C8 | 1.4 (18) |
C10—C9—C8—N2 | −3.6 (18) | C3—C4—C5—S1 | 177.3 (8) |
N1—S1—C5—C4 | −179.0 (12) | C3—C4—C5—C6 | 3.8 (18) |
N1—S1—C5—C6 | −4.5 (8) | C3—C2—C1—C6 | 0.3 (19) |
N1—C7—C6—C5 | 0.4 (17) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 2.001 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 27.035 (13) Å | Cell parameters from 3073 reflections |
b = 7.6231 (15) Å | θ = 3.1–24.9° |
c = 12.507 (3) Å | µ = 2.65 mm−1 |
β = 88.799 (11)° | T = 296 K |
V = 2577.1 (14) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 603 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.053 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0663 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.8630.
The λ/2 correction factor is Not present. | θmax = 23.2°, θmin = 1.8° |
Tmin = 0.486, Tmax = 0.563 | h = −11→11 |
9685 measured reflections | k = −8→8 |
773 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0416P)2 + 22.312P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
773 reflections | Δρmax = 0.54 e Å−3 |
71 parameters | Δρmin = −0.39 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28293 (7) | 0.39805 (9) | 0.47871 (5) | 0.0428 (10) | |
S1 | 0.4030 (2) | 0.4759 (4) | 0.4496 (2) | 0.043 (4) | |
N2 | 0.2166 (7) | 0.3840 (12) | 0.5893 (6) | 0.042 | |
O3 | 0.3284 (7) | 0.4070 (10) | 0.2097 (6) | 0.050 | |
O1 | 0.3946 (7) | 0.6223 (10) | 0.5178 (5) | 0.055 | |
C7 | 0.3594 (11) | 0.4394 (14) | 0.2748 (9) | 0.039 | |
C4 | 0.4884 (7) | 0.5959 (16) | 0.3303 (8) | 0.045 | |
H4 | 0.5069 | 0.6117 | 0.3913 | 0.054* | |
C10 | 0.1369 (8) | 0.4162 (14) | 0.7328 (8) | 0.043 | |
H10 | 0.1110 | 0.4281 | 0.7824 | 0.052* | |
N1 | 0.3530 (8) | 0.4264 (11) | 0.3829 (7) | 0.039 | |
C12 | 0.2198 (8) | 0.3256 (13) | 0.6880 (7) | 0.045 | |
H12 | 0.2490 | 0.2732 | 0.7091 | 0.054* | |
C5 | 0.4394 (7) | 0.5368 (13) | 0.3352 (7) | 0.032 | |
O2 | 0.4236 (7) | 0.3225 (10) | 0.4988 (5) | 0.050 | |
C6 | 0.4095 (9) | 0.5019 (14) | 0.2469 (7) | 0.034 | |
C9 | 0.1317 (9) | 0.4755 (14) | 0.6293 (8) | 0.043 | |
H9 | 0.1024 | 0.5255 | 0.6060 | 0.052* | |
C2 | 0.4798 (7) | 0.6006 (15) | 0.1375 (9) | 0.045 | |
H2 | 0.4935 | 0.6241 | 0.0702 | 0.054* | |
C8 | 0.1739 (8) | 0.4552 (14) | 0.5605 (8) | 0.035 | |
H8 | 0.1715 | 0.4944 | 0.4904 | 0.042* | |
C1 | 0.4315 (7) | 0.5367 (15) | 0.1463 (8) | 0.038 | |
H1 | 0.4136 | 0.5169 | 0.0848 | 0.046* | |
C11 | 0.1805 (8) | 0.3398 (14) | 0.7623 (9) | 0.047 | |
H11 | 0.1840 | 0.2974 | 0.8314 | 0.057* | |
C3 | 0.5075 (9) | 0.6296 (14) | 0.2279 (7) | 0.051 | |
H3 | 0.5396 | 0.6723 | 0.2201 | 0.061* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.047 (3) | 0.0412 (5) | 0.0399 (5) | −0.0013 (6) | 0.0018 (6) | 0.0016 (3) |
S1 | 0.048 (13) | 0.0496 (18) | 0.0305 (15) | −0.004 (3) | 0.000 (2) | 0.0017 (12) |
N2 | 0.042 | 0.041 | 0.041 | 0.000 | 0.002 | 0.001 |
O3 | 0.039 | 0.068 | 0.043 | 0.000 | 0.000 | 0.000 |
O1 | 0.057 | 0.074 | 0.035 | 0.000 | 0.001 | 0.000 |
C7 | 0.038 | 0.043 | 0.038 | 0.006 | 0.000 | 0.000 |
C4 | 0.032 | 0.053 | 0.049 | 0.000 | 0.000 | 0.000 |
C10 | 0.042 | 0.048 | 0.039 | 0.000 | 0.015 | 0.000 |
N1 | 0.035 | 0.048 | 0.034 | 0.000 | 0.000 | 0.002 |
C12 | 0.057 | 0.037 | 0.041 | 0.000 | 0.000 | 0.005 |
C5 | 0.033 | 0.032 | 0.032 | 0.000 | 0.000 | 0.000 |
O2 | 0.046 | 0.057 | 0.047 | 0.000 | 0.000 | 0.015 |
C6 | 0.025 | 0.040 | 0.037 | 0.007 | 0.000 | 0.000 |
C9 | 0.034 | 0.048 | 0.047 | 0.017 | 0.000 | 0.000 |
C2 | 0.042 | 0.051 | 0.043 | 0.004 | 0.010 | 0.005 |
C8 | 0.023 | 0.046 | 0.034 | 0.000 | 0.000 | 0.005 |
C1 | 0.034 | 0.051 | 0.029 | 0.007 | 0.000 | 0.000 |
C11 | 0.056 | 0.048 | 0.038 | 0.000 | 0.000 | 0.005 |
C3 | 0.033 | 0.051 | 0.068 | 0.000 | 0.009 | 0.004 |
Geometric parameters (Å, º) top
I1—N2 | 2.245 (16) | C10—C9 | 1.382 (14) |
I1—N1 | 2.231 (19) | C10—C11 | 1.37 (2) |
S1—O1 | 1.420 (8) | C12—H12 | 0.9300 |
S1—N1 | 1.65 (2) | C12—C11 | 1.40 (2) |
S1—C5 | 1.780 (15) | C5—C6 | 1.408 (14) |
S1—O2 | 1.440 (10) | C6—C1 | 1.404 (13) |
N2—C12 | 1.317 (12) | C9—H9 | 0.9300 |
N2—C8 | 1.332 (18) | C9—C8 | 1.42 (2) |
O3—C7 | 1.21 (2) | C2—H2 | 0.9300 |
C7—N1 | 1.362 (14) | C2—C1 | 1.397 (15) |
C7—C6 | 1.47 (4) | C2—C3 | 1.388 (14) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.399 (15) | C1—H1 | 0.9300 |
C4—C3 | 1.395 (13) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N1—I1—N2 | 173.9 (5) | C4—C5—S1 | 128.8 (9) |
O1—S1—N1 | 111.2 (9) | C4—C5—C6 | 125.7 (12) |
O1—S1—C5 | 110.9 (6) | C6—C5—S1 | 105.3 (11) |
O1—S1—O2 | 116.1 (5) | C5—C6—C7 | 114.5 (11) |
N1—S1—C5 | 95.6 (7) | C1—C6—C7 | 130.1 (14) |
O2—S1—N1 | 111.1 (7) | C1—C6—C5 | 115.4 (15) |
O2—S1—C5 | 110.0 (8) | C10—C9—H9 | 122.1 |
C12—N2—I1 | 121.8 (13) | C10—C9—C8 | 115.7 (17) |
C12—N2—C8 | 117.7 (15) | C8—C9—H9 | 122.1 |
C8—N2—I1 | 120.0 (8) | C1—C2—H2 | 119.6 |
O3—C7—N1 | 125 (2) | C3—C2—H2 | 119.6 |
O3—C7—C6 | 123.7 (12) | C3—C2—C1 | 120.8 (13) |
N1—C7—C6 | 110.9 (19) | N2—C8—C9 | 124.8 (12) |
C5—C4—H4 | 122.2 | N2—C8—H8 | 117.6 |
C3—C4—H4 | 122.2 | C9—C8—H8 | 117.6 |
C3—C4—C5 | 115.6 (14) | C6—C1—H1 | 119.5 |
C9—C10—H10 | 120.1 | C2—C1—C6 | 120.9 (13) |
C11—C10—H10 | 120.1 | C2—C1—H1 | 119.5 |
C11—C10—C9 | 119.7 (18) | C10—C11—C12 | 119.9 (12) |
S1—N1—I1 | 116.5 (5) | C10—C11—H11 | 120.0 |
C7—N1—I1 | 129.0 (17) | C12—C11—H11 | 120.0 |
C7—N1—S1 | 113.4 (17) | C4—C3—H3 | 119.3 |
N2—C12—H12 | 118.9 | C2—C3—C4 | 121.5 (17) |
N2—C12—C11 | 122.2 (16) | C2—C3—H3 | 119.3 |
C11—C12—H12 | 118.9 | | |
| | | |
I1—N2—C12—C11 | 170.5 (9) | N1—C7—C6—C1 | −178.7 (11) |
I1—N2—C8—C9 | −170.9 (10) | C12—N2—C8—C9 | 1.1 (19) |
S1—C5—C6—C7 | 3.2 (14) | C5—S1—N1—I1 | −165.4 (6) |
S1—C5—C6—C1 | −178.6 (9) | C5—S1—N1—C7 | 3.7 (10) |
N2—C12—C11—C10 | 0.2 (19) | C5—C4—C3—C2 | −1.8 (18) |
O3—C7—N1—I1 | −13.8 (18) | C5—C6—C1—C2 | 0.3 (17) |
O3—C7—N1—S1 | 178.7 (11) | O2—S1—N1—I1 | 80.6 (8) |
O3—C7—C6—C5 | 178.2 (12) | O2—S1—N1—C7 | −110.3 (9) |
O3—C7—C6—C1 | 0 (3) | O2—S1—C5—C4 | −65.1 (14) |
O1—S1—N1—I1 | −50.4 (6) | O2—S1—C5—C6 | 111.0 (9) |
O1—S1—N1—C7 | 118.7 (9) | C6—C7—N1—I1 | 165.1 (10) |
O1—S1—C5—C4 | 64.7 (16) | C6—C7—N1—S1 | −2.3 (15) |
O1—S1—C5—C6 | −119.2 (10) | C9—C10—C11—C12 | 1 (2) |
C7—C6—C1—C2 | 178.2 (16) | C8—N2—C12—C11 | −1.4 (19) |
C4—C5—C6—C7 | 179.5 (15) | C1—C2—C3—C4 | 0.1 (19) |
C4—C5—C6—C1 | −2.3 (18) | C11—C10—C9—C8 | −1.5 (19) |
C10—C9—C8—N2 | 0.3 (19) | C3—C4—C5—S1 | 178.4 (9) |
N1—S1—C5—C4 | −180.0 (13) | C3—C4—C5—C6 | 3.1 (19) |
N1—S1—C5—C6 | −3.8 (8) | C3—C2—C1—C6 | 1 (2) |
N1—C7—C6—C5 | −0.8 (18) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 2.061 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.869 (13) Å | Cell parameters from 3197 reflections |
b = 7.4985 (14) Å | θ = 3.1–22.0° |
c = 12.418 (3) Å | µ = 2.73 mm−1 |
β = 88.952 (10)° | T = 296 K |
V = 2501.5 (14) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 603 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.049 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0633 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.8516.
The λ/2 correction factor is Not present. | θmax = 23.2°, θmin = 1.8° |
Tmin = 0.479, Tmax = 0.563 | h = −11→11 |
9489 measured reflections | k = −8→8 |
759 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0423P)2 + 29.2986P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max < 0.001 |
759 reflections | Δρmax = 0.82 e Å−3 |
71 parameters | Δρmin = −0.49 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28186 (7) | 0.39836 (9) | 0.47820 (5) | 0.0373 (10) | |
S1 | 0.4022 (3) | 0.4777 (4) | 0.4498 (2) | 0.041 (4) | |
N2 | 0.2162 (7) | 0.3846 (12) | 0.5888 (6) | 0.034 | |
O3 | 0.3288 (7) | 0.4043 (11) | 0.2070 (6) | 0.043 | |
O1 | 0.3941 (7) | 0.6278 (10) | 0.5184 (5) | 0.047 | |
C7 | 0.3601 (10) | 0.4379 (13) | 0.2727 (8) | 0.028 | |
C4 | 0.4876 (7) | 0.5971 (16) | 0.3329 (9) | 0.041 | |
H4 | 0.5058 | 0.6122 | 0.3952 | 0.049* | |
C10 | 0.1369 (8) | 0.4165 (14) | 0.7345 (8) | 0.038 | |
H10 | 0.1108 | 0.4270 | 0.7842 | 0.045* | |
N1 | 0.3523 (8) | 0.4281 (12) | 0.3814 (7) | 0.035 | |
C12 | 0.2198 (9) | 0.3253 (14) | 0.6900 (8) | 0.041 | |
H12 | 0.2493 | 0.2720 | 0.7111 | 0.049* | |
C5 | 0.4380 (7) | 0.5395 (14) | 0.3355 (8) | 0.031 | |
O2 | 0.4215 (7) | 0.3211 (10) | 0.5007 (6) | 0.044 | |
C6 | 0.4088 (9) | 0.5040 (14) | 0.2452 (7) | 0.026 | |
C9 | 0.1314 (9) | 0.4772 (14) | 0.6301 (8) | 0.036 | |
H9 | 0.1019 | 0.5284 | 0.6075 | 0.043* | |
C2 | 0.4812 (7) | 0.5981 (17) | 0.1379 (9) | 0.046 | |
H2 | 0.4960 | 0.6178 | 0.0706 | 0.055* | |
C8 | 0.1723 (8) | 0.4578 (15) | 0.5605 (9) | 0.030 | |
H8 | 0.1693 | 0.4977 | 0.4900 | 0.036* | |
C1 | 0.4323 (7) | 0.5357 (15) | 0.1452 (8) | 0.035 | |
H1 | 0.4148 | 0.5149 | 0.0824 | 0.042* | |
C11 | 0.1810 (8) | 0.3410 (15) | 0.7640 (9) | 0.044 | |
H11 | 0.1849 | 0.3001 | 0.8340 | 0.052* | |
C3 | 0.5079 (9) | 0.6307 (15) | 0.2302 (7) | 0.045 | |
H3 | 0.5401 | 0.6759 | 0.2240 | 0.054* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.041 (3) | 0.0354 (4) | 0.0351 (5) | −0.0017 (6) | 0.0003 (6) | 0.0012 (3) |
S1 | 0.059 (12) | 0.0394 (17) | 0.0252 (15) | −0.003 (2) | 0.001 (2) | 0.0013 (12) |
N2 | 0.034 | 0.034 | 0.034 | 0.000 | 0.002 | 0.001 |
O3 | 0.034 | 0.059 | 0.037 | 0.000 | 0.000 | 0.000 |
O1 | 0.048 | 0.063 | 0.029 | 0.000 | 0.001 | 0.000 |
C7 | 0.027 | 0.030 | 0.027 | 0.004 | 0.000 | 0.000 |
C4 | 0.030 | 0.048 | 0.044 | 0.000 | 0.000 | 0.000 |
C10 | 0.036 | 0.042 | 0.034 | 0.000 | 0.013 | 0.000 |
N1 | 0.032 | 0.044 | 0.031 | 0.000 | 0.000 | 0.002 |
C12 | 0.052 | 0.034 | 0.038 | 0.000 | 0.000 | 0.004 |
C5 | 0.031 | 0.030 | 0.031 | 0.000 | 0.000 | 0.000 |
O2 | 0.040 | 0.050 | 0.041 | 0.000 | 0.000 | 0.013 |
C6 | 0.019 | 0.030 | 0.028 | 0.005 | 0.000 | 0.000 |
C9 | 0.029 | 0.040 | 0.039 | 0.015 | 0.000 | 0.000 |
C2 | 0.042 | 0.052 | 0.043 | 0.004 | 0.010 | 0.005 |
C8 | 0.020 | 0.040 | 0.029 | 0.000 | 0.000 | 0.004 |
C1 | 0.032 | 0.047 | 0.027 | 0.007 | 0.000 | 0.000 |
C11 | 0.051 | 0.045 | 0.035 | 0.000 | 0.000 | 0.005 |
C3 | 0.029 | 0.046 | 0.061 | 0.000 | 0.008 | 0.003 |
Geometric parameters (Å, º) top
I1—N2 | 2.219 (16) | C10—C9 | 1.384 (14) |
I1—N1 | 2.233 (19) | C10—C11 | 1.37 (2) |
S1—O1 | 1.427 (8) | C12—H12 | 0.9300 |
S1—N1 | 1.64 (2) | C12—C11 | 1.38 (2) |
S1—C5 | 1.762 (15) | C5—C6 | 1.406 (14) |
S1—O2 | 1.434 (11) | C6—C1 | 1.401 (13) |
N2—C12 | 1.338 (13) | C9—H9 | 0.9300 |
N2—C8 | 1.352 (18) | C9—C8 | 1.39 (2) |
O3—C7 | 1.21 (2) | C2—H2 | 0.9300 |
C7—N1 | 1.365 (14) | C2—C1 | 1.398 (15) |
C7—C6 | 1.44 (3) | C2—C3 | 1.386 (14) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.399 (15) | C1—H1 | 0.9300 |
C4—C3 | 1.401 (13) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N2—I1—N1 | 173.7 (5) | C4—C5—S1 | 127.2 (9) |
O1—S1—N1 | 111.7 (9) | C4—C5—C6 | 125.7 (13) |
O1—S1—C5 | 110.4 (6) | C6—C5—S1 | 106.8 (11) |
O1—S1—O2 | 115.8 (5) | C5—C6—C7 | 113.3 (11) |
N1—S1—C5 | 94.7 (7) | C1—C6—C7 | 131.5 (14) |
O2—S1—N1 | 110.3 (7) | C1—C6—C5 | 115.2 (14) |
O2—S1—C5 | 112.0 (8) | C10—C9—H9 | 121.6 |
C12—N2—I1 | 121.7 (13) | C10—C9—C8 | 116.8 (17) |
C12—N2—C8 | 117.3 (15) | C8—C9—H9 | 121.6 |
C8—N2—I1 | 120.5 (8) | C1—C2—H2 | 119.8 |
O3—C7—N1 | 124 (2) | C3—C2—H2 | 119.8 |
O3—C7—C6 | 123.6 (12) | C3—C2—C1 | 120.4 (14) |
N1—C7—C6 | 112.1 (18) | N2—C8—C9 | 124.2 (12) |
C5—C4—H4 | 122.2 | N2—C8—H8 | 117.9 |
C5—C4—C3 | 115.7 (15) | C9—C8—H8 | 117.9 |
C3—C4—H4 | 122.2 | C6—C1—H1 | 119.3 |
C9—C10—H10 | 120.2 | C2—C1—C6 | 121.4 (13) |
C11—C10—H10 | 120.2 | C2—C1—H1 | 119.3 |
C11—C10—C9 | 119.6 (17) | C10—C11—C12 | 120.2 (13) |
S1—N1—I1 | 115.9 (5) | C10—C11—H11 | 119.9 |
C7—N1—I1 | 130.6 (17) | C12—C11—H11 | 119.9 |
C7—N1—S1 | 112.7 (17) | C4—C3—H3 | 119.3 |
N2—C12—H12 | 119.1 | C2—C3—C4 | 121.4 (17) |
N2—C12—C11 | 121.9 (17) | C2—C3—H3 | 119.3 |
C11—C12—H12 | 119.1 | | |
| | | |
I1—N2—C12—C11 | 170.2 (10) | N1—C7—C6—C1 | −179.7 (12) |
I1—N2—C8—C9 | −170.7 (10) | C12—N2—C8—C9 | 1.0 (19) |
S1—C5—C6—C7 | 2.3 (13) | C5—S1—N1—I1 | −165.5 (6) |
S1—C5—C6—C1 | −176.6 (9) | C5—S1—N1—C7 | 5.6 (9) |
N2—C12—C11—C10 | 1 (2) | C5—C4—C3—C2 | −3.7 (18) |
O3—C7—N1—I1 | −11.9 (17) | C5—C6—C1—C2 | 0.1 (18) |
O3—C7—N1—S1 | 178.8 (11) | O2—S1—N1—I1 | 79.0 (8) |
O3—C7—C6—C5 | 177.7 (12) | O2—S1—N1—C7 | −110.0 (9) |
O3—C7—C6—C1 | −4 (3) | O2—S1—C5—C4 | −64.8 (14) |
O1—S1—N1—I1 | −51.3 (6) | O2—S1—C5—C6 | 109.7 (10) |
O1—S1—N1—C7 | 119.7 (9) | C6—C7—N1—I1 | 164.3 (10) |
O1—S1—C5—C4 | 65.8 (15) | C6—C7—N1—S1 | −5.0 (15) |
O1—S1—C5—C6 | −119.7 (10) | C9—C10—C11—C12 | 0 (2) |
C7—C6—C1—C2 | −178.7 (16) | C8—N2—C12—C11 | −1.4 (19) |
C4—C5—C6—C7 | 177.0 (14) | C1—C2—C3—C4 | 2 (2) |
C4—C5—C6—C1 | −2.0 (18) | C11—C10—C9—C8 | −0.4 (19) |
C10—C9—C8—N2 | −0.1 (19) | C3—C4—C5—S1 | 177.3 (9) |
N1—S1—C5—C4 | −179.0 (13) | C3—C4—C5—C6 | 3.7 (19) |
N1—S1—C5—C6 | −4.4 (9) | C3—C2—C1—C6 | 0 (2) |
N1—C7—C6—C5 | 1.5 (17) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 2.087 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.806 (12) Å | Cell parameters from 3682 reflections |
b = 7.4450 (14) Å | θ = 3.1–24.3° |
c = 12.380 (2) Å | µ = 2.77 mm−1 |
β = 89.057 (10)° | T = 296 K |
V = 2470.4 (13) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 573 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.046 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. | θmax = 23.2°, θmin = 1.8° |
Tmin = 0.461, Tmax = 0.563 | h = −10→10 |
9464 measured reflections | k = −8→8 |
706 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0368P)2 + 25.1886P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max < 0.001 |
706 reflections | Δρmax = 0.82 e Å−3 |
71 parameters | Δρmin = −0.43 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28149 (6) | 0.39844 (9) | 0.47798 (5) | 0.0334 (10) | |
S1 | 0.4022 (2) | 0.4789 (3) | 0.44983 (18) | 0.037 (4) | |
N2 | 0.2165 (7) | 0.3868 (11) | 0.5890 (6) | 0.032 | |
O3 | 0.3292 (7) | 0.4050 (10) | 0.2060 (6) | 0.040 | |
O1 | 0.3931 (7) | 0.6310 (10) | 0.5182 (5) | 0.044 | |
C7 | 0.3602 (10) | 0.4380 (12) | 0.2718 (8) | 0.022 | |
C4 | 0.4869 (7) | 0.5979 (16) | 0.3321 (8) | 0.041 | |
H4 | 0.5050 | 0.6148 | 0.3947 | 0.049* | |
C10 | 0.1374 (8) | 0.4178 (13) | 0.7348 (8) | 0.032 | |
H10 | 0.1116 | 0.4281 | 0.7855 | 0.039* | |
N1 | 0.3512 (8) | 0.4287 (11) | 0.3804 (6) | 0.033 | |
C12 | 0.2209 (8) | 0.3256 (13) | 0.6911 (7) | 0.036 | |
H12 | 0.2505 | 0.2712 | 0.7119 | 0.043* | |
C5 | 0.4376 (7) | 0.5393 (13) | 0.3360 (7) | 0.026 | |
O2 | 0.4214 (6) | 0.3224 (9) | 0.5014 (5) | 0.039 | |
C6 | 0.4096 (9) | 0.5041 (13) | 0.2447 (6) | 0.026 | |
C9 | 0.1297 (8) | 0.4787 (13) | 0.6308 (7) | 0.032 | |
H9 | 0.0998 | 0.5288 | 0.6090 | 0.038* | |
C2 | 0.4814 (7) | 0.5987 (15) | 0.1378 (8) | 0.038 | |
H2 | 0.4963 | 0.6194 | 0.0706 | 0.046* | |
C8 | 0.1714 (7) | 0.4582 (14) | 0.5607 (8) | 0.026 | |
H8 | 0.1679 | 0.4960 | 0.4896 | 0.031* | |
C1 | 0.4326 (7) | 0.5361 (14) | 0.1444 (7) | 0.030 | |
H1 | 0.4151 | 0.5152 | 0.0814 | 0.036* | |
C11 | 0.1814 (8) | 0.3432 (13) | 0.7659 (8) | 0.035 | |
H11 | 0.1852 | 0.3041 | 0.8366 | 0.042* | |
C3 | 0.5078 (9) | 0.6302 (14) | 0.2305 (7) | 0.040 | |
H3 | 0.5402 | 0.6739 | 0.2249 | 0.048* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.038 (3) | 0.0305 (4) | 0.0320 (4) | −0.0012 (6) | 0.0027 (6) | 0.0013 (3) |
S1 | 0.052 (13) | 0.0350 (15) | 0.0233 (13) | −0.004 (2) | 0.001 (2) | 0.0016 (11) |
N2 | 0.032 | 0.032 | 0.032 | 0.000 | 0.002 | 0.001 |
O3 | 0.031 | 0.054 | 0.034 | 0.000 | 0.000 | 0.000 |
O1 | 0.046 | 0.060 | 0.028 | 0.000 | 0.001 | 0.000 |
C7 | 0.022 | 0.024 | 0.021 | 0.003 | 0.000 | 0.000 |
C4 | 0.029 | 0.048 | 0.044 | 0.000 | 0.000 | 0.000 |
C10 | 0.031 | 0.036 | 0.030 | 0.000 | 0.011 | 0.000 |
N1 | 0.030 | 0.040 | 0.028 | 0.000 | 0.000 | 0.002 |
C12 | 0.045 | 0.029 | 0.033 | 0.000 | 0.000 | 0.004 |
C5 | 0.027 | 0.026 | 0.026 | 0.000 | 0.000 | 0.000 |
O2 | 0.035 | 0.045 | 0.036 | 0.000 | 0.000 | 0.012 |
C6 | 0.020 | 0.031 | 0.029 | 0.005 | 0.000 | 0.000 |
C9 | 0.025 | 0.035 | 0.035 | 0.013 | 0.000 | 0.000 |
C2 | 0.035 | 0.043 | 0.036 | 0.003 | 0.009 | 0.004 |
C8 | 0.018 | 0.035 | 0.026 | 0.000 | 0.000 | 0.004 |
C1 | 0.027 | 0.041 | 0.023 | 0.006 | 0.000 | 0.000 |
C11 | 0.041 | 0.036 | 0.028 | 0.000 | 0.000 | 0.004 |
C3 | 0.026 | 0.040 | 0.054 | 0.000 | 0.007 | 0.003 |
Geometric parameters (Å, º) top
I1—N2 | 2.203 (15) | C10—C9 | 1.385 (13) |
I1—N1 | 2.220 (18) | C10—C11 | 1.364 (19) |
S1—O1 | 1.433 (8) | C12—H12 | 0.9300 |
S1—N1 | 1.67 (2) | C12—C11 | 1.40 (2) |
S1—C5 | 1.745 (14) | C5—C6 | 1.393 (14) |
S1—O2 | 1.430 (10) | C6—C1 | 1.398 (13) |
N2—C12 | 1.350 (12) | C9—H9 | 0.9300 |
N2—C8 | 1.373 (18) | C9—C8 | 1.41 (2) |
O3—C7 | 1.20 (2) | C2—H2 | 0.9300 |
C7—N1 | 1.364 (13) | C2—C1 | 1.389 (15) |
C7—C6 | 1.45 (3) | C2—C3 | 1.379 (14) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.392 (15) | C1—H1 | 0.9300 |
C4—C3 | 1.390 (13) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N2—I1—N1 | 173.5 (4) | C4—C5—S1 | 127.8 (8) |
O1—S1—N1 | 110.4 (9) | C4—C5—C6 | 123.7 (13) |
O1—S1—C5 | 111.0 (6) | C6—C5—S1 | 108.3 (11) |
N1—S1—C5 | 94.7 (7) | C5—C6—C7 | 112.3 (11) |
O2—S1—O1 | 116.1 (5) | C5—C6—C1 | 117.0 (14) |
O2—S1—N1 | 110.7 (7) | C1—C6—C7 | 130.8 (13) |
O2—S1—C5 | 112.0 (8) | C10—C9—H9 | 123.0 |
C12—N2—I1 | 121.1 (12) | C10—C9—C8 | 114.1 (16) |
C12—N2—C8 | 117.4 (14) | C8—C9—H9 | 123.0 |
C8—N2—I1 | 121.1 (7) | C1—C2—H2 | 119.8 |
O3—C7—N1 | 123 (2) | C3—C2—H2 | 119.8 |
O3—C7—C6 | 123.6 (11) | C3—C2—C1 | 120.3 (13) |
N1—C7—C6 | 113.1 (17) | N2—C8—C9 | 125.2 (11) |
C5—C4—H4 | 121.5 | N2—C8—H8 | 117.4 |
C3—C4—H4 | 121.5 | C9—C8—H8 | 117.4 |
C3—C4—C5 | 117.0 (14) | C6—C1—H1 | 119.7 |
C9—C10—H10 | 118.7 | C2—C1—C6 | 120.7 (13) |
C11—C10—H10 | 118.7 | C2—C1—H1 | 119.7 |
C11—C10—C9 | 122.6 (16) | C10—C11—C12 | 119.9 (12) |
S1—N1—I1 | 115.6 (4) | C10—C11—H11 | 120.0 |
C7—N1—I1 | 132.4 (16) | C12—C11—H11 | 120.0 |
C7—N1—S1 | 111.3 (16) | C4—C3—H3 | 119.4 |
N2—C12—H12 | 119.7 | C2—C3—C4 | 121.2 (16) |
N2—C12—C11 | 120.7 (15) | C2—C3—H3 | 119.4 |
C11—C12—H12 | 119.7 | | |
| | | |
I1—N2—C12—C11 | 170.5 (9) | N1—C7—C6—C1 | −178.7 (11) |
I1—N2—C8—C9 | −171.1 (9) | C12—N2—C8—C9 | 2.4 (18) |
S1—C5—C6—C7 | 2.7 (13) | C5—S1—N1—I1 | −166.0 (5) |
S1—C5—C6—C1 | −177.1 (9) | C5—S1—N1—C7 | 5.9 (9) |
N2—C12—C11—C10 | 2.0 (18) | C5—C4—C3—C2 | −2.4 (17) |
O3—C7—N1—I1 | −10.9 (16) | C5—C6—C1—C2 | 0.6 (17) |
O3—C7—N1—S1 | 178.9 (10) | O2—S1—N1—I1 | 78.3 (7) |
O3—C7—C6—C5 | 177.3 (11) | O2—S1—N1—C7 | −109.7 (8) |
O3—C7—C6—C1 | −3 (2) | O2—S1—C5—C4 | −65.1 (13) |
O1—S1—N1—I1 | −51.6 (6) | O2—S1—C5—C6 | 109.6 (10) |
O1—S1—N1—C7 | 120.4 (8) | C6—C7—N1—I1 | 164.9 (10) |
O1—S1—C5—C4 | 66.4 (15) | C6—C7—N1—S1 | −5.3 (14) |
O1—S1—C5—C6 | −118.9 (10) | C9—C10—C11—C12 | −0.1 (18) |
C7—C6—C1—C2 | −179.2 (15) | C8—N2—C12—C11 | −3.1 (17) |
C4—C5—C6—C7 | 177.6 (13) | C1—C2—C3—C4 | 1.0 (18) |
C4—C5—C6—C1 | −2.2 (17) | C11—C10—C9—C8 | −0.5 (17) |
C10—C9—C8—N2 | −0.6 (17) | C3—C4—C5—S1 | 177.0 (9) |
N1—S1—C5—C4 | −179.6 (12) | C3—C4—C5—C6 | 3.1 (18) |
N1—S1—C5—C6 | −4.9 (8) | C3—C2—C1—C6 | 0.0 (19) |
N1—C7—C6—C5 | 1.5 (17) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 2.117 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.742 (14) Å | Cell parameters from 3223 reflections |
b = 7.3842 (15) Å | θ = 3.2–25.9° |
c = 12.337 (3) Å | µ = 2.81 mm−1 |
β = 89.154 (11)° | T = 296 K |
V = 2436.0 (15) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 582 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.053 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0628 before and 0.0541 after correction.
The Ratio of minimum to maximum transmission is 0.8665.
The λ/2 correction factor is Not present. | θmax = 23.3°, θmin = 1.8° |
Tmin = 0.488, Tmax = 0.563 | h = −11→11 |
8933 measured reflections | k = −8→8 |
712 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0253P)2 + 80.1818P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max < 0.001 |
712 reflections | Δρmax = 0.72 e Å−3 |
71 parameters | Δρmin = −0.41 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28091 (9) | 0.39881 (12) | 0.47764 (7) | 0.0319 (12) | |
S1 | 0.4016 (3) | 0.4806 (5) | 0.4501 (3) | 0.037 (5) | |
N2 | 0.2164 (9) | 0.3876 (15) | 0.5891 (8) | 0.030 | |
O3 | 0.3286 (9) | 0.4023 (14) | 0.2044 (8) | 0.038 | |
O1 | 0.3938 (9) | 0.6329 (13) | 0.5183 (7) | 0.038 | |
C7 | 0.3598 (13) | 0.4378 (17) | 0.2700 (11) | 0.025 | |
C4 | 0.4869 (9) | 0.600 (2) | 0.3337 (11) | 0.040 | |
H4 | 0.5051 | 0.6168 | 0.3965 | 0.048* | |
C10 | 0.1367 (10) | 0.4178 (19) | 0.7365 (10) | 0.034 | |
H10 | 0.1102 | 0.4246 | 0.7861 | 0.040* | |
N1 | 0.3505 (11) | 0.4296 (15) | 0.3794 (9) | 0.031 | |
C12 | 0.2205 (11) | 0.3260 (18) | 0.6916 (10) | 0.036 | |
H12 | 0.2500 | 0.2699 | 0.7120 | 0.043* | |
C5 | 0.4375 (9) | 0.5401 (17) | 0.3371 (10) | 0.024 | |
O2 | 0.4209 (9) | 0.3224 (13) | 0.5024 (7) | 0.036 | |
C6 | 0.4099 (12) | 0.5059 (18) | 0.2440 (8) | 0.024 | |
C9 | 0.1311 (11) | 0.4819 (18) | 0.6309 (10) | 0.032 | |
H9 | 0.1015 | 0.5358 | 0.6087 | 0.038* | |
C2 | 0.4819 (9) | 0.598 (2) | 0.1379 (11) | 0.039 | |
H2 | 0.4973 | 0.6170 | 0.0707 | 0.046* | |
C8 | 0.1714 (10) | 0.4616 (19) | 0.5609 (11) | 0.026 | |
H8 | 0.1678 | 0.5007 | 0.4898 | 0.032* | |
C1 | 0.4329 (9) | 0.535 (2) | 0.1437 (10) | 0.032 | |
H1 | 0.4155 | 0.5131 | 0.0804 | 0.039* | |
C11 | 0.1824 (10) | 0.3435 (18) | 0.7669 (11) | 0.034 | |
H11 | 0.1871 | 0.3059 | 0.8380 | 0.041* | |
C3 | 0.5076 (12) | 0.6331 (19) | 0.2320 (9) | 0.039 | |
H3 | 0.5398 | 0.6802 | 0.2269 | 0.046* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.034 (4) | 0.0300 (5) | 0.0318 (5) | −0.0013 (8) | 0.0018 (7) | 0.0013 (4) |
S1 | 0.053 (17) | 0.035 (2) | 0.0228 (18) | −0.005 (3) | 0.000 (3) | 0.0017 (15) |
N2 | 0.030 | 0.030 | 0.030 | 0.000 | 0.002 | 0.001 |
O3 | 0.030 | 0.052 | 0.033 | 0.000 | 0.000 | 0.000 |
O1 | 0.039 | 0.051 | 0.024 | 0.000 | 0.001 | 0.000 |
C7 | 0.024 | 0.027 | 0.024 | 0.004 | 0.000 | 0.000 |
C4 | 0.029 | 0.047 | 0.043 | 0.000 | 0.000 | 0.000 |
C10 | 0.032 | 0.037 | 0.031 | 0.000 | 0.012 | 0.000 |
N1 | 0.028 | 0.038 | 0.026 | 0.000 | 0.000 | 0.002 |
C12 | 0.045 | 0.029 | 0.033 | 0.000 | 0.000 | 0.004 |
C5 | 0.024 | 0.023 | 0.024 | 0.000 | 0.000 | 0.000 |
O2 | 0.033 | 0.042 | 0.034 | 0.000 | 0.000 | 0.011 |
C6 | 0.018 | 0.028 | 0.026 | 0.005 | 0.000 | 0.000 |
C9 | 0.025 | 0.035 | 0.035 | 0.013 | 0.000 | 0.000 |
C2 | 0.036 | 0.043 | 0.037 | 0.003 | 0.009 | 0.004 |
C8 | 0.018 | 0.035 | 0.026 | 0.000 | 0.000 | 0.004 |
C1 | 0.029 | 0.043 | 0.025 | 0.006 | 0.000 | 0.000 |
C11 | 0.040 | 0.035 | 0.028 | 0.000 | 0.000 | 0.004 |
C3 | 0.025 | 0.039 | 0.052 | 0.000 | 0.007 | 0.003 |
Geometric parameters (Å, º) top
I1—N2 | 2.192 (19) | C10—C9 | 1.397 (17) |
I1—N1 | 2.22 (2) | C10—C11 | 1.40 (2) |
S1—O1 | 1.419 (10) | C12—H12 | 0.9300 |
S1—N1 | 1.68 (3) | C12—C11 | 1.37 (3) |
S1—C5 | 1.737 (19) | C5—C6 | 1.398 (16) |
S1—O2 | 1.434 (13) | C6—C1 | 1.390 (15) |
N2—C12 | 1.351 (16) | C9—H9 | 0.9300 |
N2—C8 | 1.37 (2) | C9—C8 | 1.38 (3) |
O3—C7 | 1.20 (3) | C2—H2 | 0.9300 |
C7—N1 | 1.370 (18) | C2—C1 | 1.390 (17) |
C7—C6 | 1.46 (4) | C2—C3 | 1.383 (16) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.394 (17) | C1—H1 | 0.9300 |
C4—C3 | 1.384 (15) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N2—I1—N1 | 173.3 (6) | C4—C5—S1 | 128.1 (11) |
O1—S1—N1 | 111.8 (11) | C4—C5—C6 | 123.0 (17) |
O1—S1—C5 | 110.5 (7) | C6—C5—S1 | 108.8 (14) |
O1—S1—O2 | 115.4 (6) | C5—C6—C7 | 112.0 (14) |
N1—S1—C5 | 94.9 (8) | C1—C6—C7 | 129.9 (18) |
O2—S1—N1 | 110.7 (9) | C1—C6—C5 | 118.1 (19) |
O2—S1—C5 | 111.7 (10) | C10—C9—H9 | 121.5 |
C12—N2—I1 | 121.8 (16) | C8—C9—C10 | 117 (2) |
C12—N2—C8 | 117.1 (19) | C8—C9—H9 | 121.5 |
C8—N2—I1 | 120.8 (10) | C1—C2—H2 | 120.1 |
O3—C7—N1 | 122 (3) | C3—C2—H2 | 120.1 |
O3—C7—C6 | 124.8 (15) | C3—C2—C1 | 119.9 (17) |
N1—C7—C6 | 113 (2) | N2—C8—C9 | 124.4 (16) |
C5—C4—H4 | 121.7 | N2—C8—H8 | 117.8 |
C3—C4—H4 | 121.7 | C9—C8—H8 | 117.8 |
C3—C4—C5 | 116.7 (19) | C6—C1—C2 | 120.2 (17) |
C9—C10—H10 | 120.3 | C6—C1—H1 | 119.9 |
C11—C10—H10 | 120.3 | C2—C1—H1 | 119.9 |
C11—C10—C9 | 119 (2) | C10—C11—H11 | 120.1 |
S1—N1—I1 | 115.1 (6) | C12—C11—C10 | 119.9 (16) |
C7—N1—I1 | 133 (2) | C12—C11—H11 | 120.1 |
C7—N1—S1 | 111 (2) | C4—C3—H3 | 119.0 |
N2—C12—H12 | 118.9 | C2—C3—C4 | 122 (2) |
N2—C12—C11 | 122 (2) | C2—C3—H3 | 119.0 |
C11—C12—H12 | 118.9 | | |
| | | |
I1—N2—C12—C11 | 170.0 (13) | N1—C7—C6—C1 | −179.2 (15) |
I1—N2—C8—C9 | −171.0 (13) | C12—N2—C8—C9 | 2 (2) |
S1—C5—C6—C7 | 1.9 (17) | C5—S1—N1—I1 | −166.5 (7) |
S1—C5—C6—C1 | −176.7 (12) | C5—S1—N1—C7 | 6.0 (12) |
N2—C12—C11—C10 | 4 (2) | C5—C4—C3—C2 | −4 (2) |
O3—C7—N1—I1 | −11 (2) | C5—C6—C1—C2 | 0 (2) |
O3—C7—N1—S1 | 178.4 (13) | O2—S1—N1—I1 | 78.1 (10) |
O3—C7—C6—C5 | 178.2 (15) | O2—S1—N1—C7 | −109.4 (12) |
O3—C7—C6—C1 | −3 (3) | O2—S1—C5—C4 | −65.5 (17) |
O1—S1—N1—I1 | −52.1 (8) | O2—S1—C5—C6 | 110.0 (12) |
O1—S1—N1—C7 | 120.4 (11) | C6—C7—N1—I1 | 164.9 (13) |
O1—S1—C5—C4 | 64.5 (19) | C6—C7—N1—S1 | −5.8 (19) |
O1—S1—C5—C6 | −120.0 (13) | C9—C10—C11—C12 | −3 (2) |
C7—C6—C1—C2 | −179 (2) | C8—N2—C12—C11 | −3 (2) |
C4—C5—C6—C7 | 177.7 (18) | C1—C2—C3—C4 | 3 (3) |
C4—C5—C6—C1 | −1 (2) | C11—C10—C9—C8 | 2 (2) |
C10—C9—C8—N2 | −2 (2) | C3—C4—C5—S1 | 177.9 (12) |
N1—S1—C5—C4 | 180.0 (16) | C3—C4—C5—C6 | 3 (2) |
N1—S1—C5—C6 | −4.5 (11) | C3—C2—C1—C6 | −1 (3) |
N1—C7—C6—C5 | 2 (2) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 2.150 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.653 (12) Å | Cell parameters from 3792 reflections |
b = 7.3257 (13) Å | θ = 3.2–23.3° |
c = 12.284 (2) Å | µ = 2.85 mm−1 |
β = 89.236 (10)° | T = 296 K |
V = 2398.2 (12) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 582 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.044 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. | θmax = 23.3°, θmin = 1.8° |
Tmin = 0.461, Tmax = 0.563 | h = −10→10 |
9116 measured reflections | k = −8→8 |
688 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0269P)2 + 58.096P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
688 reflections | Δρmax = 0.85 e Å−3 |
71 parameters | Δρmin = −0.44 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28047 (8) | 0.39904 (10) | 0.47741 (6) | 0.0301 (11) | |
S1 | 0.4016 (3) | 0.4811 (4) | 0.4502 (2) | 0.037 (4) | |
N2 | 0.2163 (8) | 0.3876 (13) | 0.5893 (7) | 0.029 | |
O3 | 0.3285 (8) | 0.4022 (12) | 0.2033 (6) | 0.035 | |
O1 | 0.3925 (8) | 0.6370 (11) | 0.5181 (6) | 0.038 | |
C7 | 0.3598 (12) | 0.4375 (15) | 0.2701 (9) | 0.024 | |
C4 | 0.4876 (8) | 0.5997 (19) | 0.3346 (10) | 0.037 | |
H4 | 0.5056 | 0.6163 | 0.3982 | 0.044* | |
C10 | 0.1370 (8) | 0.4193 (15) | 0.7375 (9) | 0.029 | |
H10 | 0.1109 | 0.4285 | 0.7882 | 0.034* | |
N1 | 0.3510 (9) | 0.4292 (12) | 0.3793 (7) | 0.028 | |
C12 | 0.2209 (10) | 0.3263 (15) | 0.6931 (8) | 0.034 | |
H12 | 0.2506 | 0.2711 | 0.7143 | 0.041* | |
C5 | 0.4380 (8) | 0.5408 (15) | 0.3365 (8) | 0.023 | |
O2 | 0.4200 (7) | 0.3230 (11) | 0.5033 (6) | 0.034 | |
C6 | 0.4103 (10) | 0.5053 (15) | 0.2432 (7) | 0.023 | |
C9 | 0.1302 (9) | 0.4805 (16) | 0.6321 (9) | 0.030 | |
H9 | 0.1001 | 0.5310 | 0.6099 | 0.036* | |
C2 | 0.4826 (8) | 0.5997 (18) | 0.1385 (9) | 0.038 | |
H2 | 0.4981 | 0.6204 | 0.0713 | 0.045* | |
C8 | 0.1707 (8) | 0.4624 (16) | 0.5619 (9) | 0.026 | |
H8 | 0.1670 | 0.5036 | 0.4909 | 0.031* | |
C1 | 0.4333 (8) | 0.5361 (17) | 0.1423 (9) | 0.030 | |
H1 | 0.4160 | 0.5144 | 0.0784 | 0.036* | |
C11 | 0.1821 (9) | 0.3450 (16) | 0.7673 (9) | 0.033 | |
H11 | 0.1865 | 0.3067 | 0.8387 | 0.040* | |
C3 | 0.5089 (10) | 0.6325 (16) | 0.2328 (8) | 0.035 | |
H3 | 0.5415 | 0.6775 | 0.2278 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.033 (4) | 0.0274 (4) | 0.0294 (5) | −0.0001 (7) | 0.0022 (6) | 0.0011 (3) |
S1 | 0.062 (14) | 0.0302 (17) | 0.0198 (15) | −0.004 (3) | 0.002 (3) | 0.0011 (12) |
N2 | 0.029 | 0.029 | 0.029 | 0.000 | 0.002 | 0.001 |
O3 | 0.027 | 0.047 | 0.030 | 0.000 | 0.000 | 0.000 |
O1 | 0.039 | 0.051 | 0.024 | 0.000 | 0.001 | 0.000 |
C7 | 0.024 | 0.026 | 0.023 | 0.003 | 0.000 | 0.000 |
C4 | 0.027 | 0.043 | 0.040 | 0.000 | 0.000 | 0.000 |
C10 | 0.027 | 0.032 | 0.026 | 0.000 | 0.010 | 0.000 |
N1 | 0.025 | 0.034 | 0.024 | 0.000 | 0.000 | 0.001 |
C12 | 0.043 | 0.028 | 0.031 | 0.000 | 0.000 | 0.003 |
C5 | 0.023 | 0.023 | 0.023 | 0.000 | 0.000 | 0.000 |
O2 | 0.031 | 0.040 | 0.032 | 0.000 | 0.000 | 0.010 |
C6 | 0.017 | 0.027 | 0.025 | 0.005 | 0.000 | 0.000 |
C9 | 0.024 | 0.033 | 0.032 | 0.012 | 0.000 | 0.000 |
C2 | 0.035 | 0.042 | 0.036 | 0.003 | 0.009 | 0.004 |
C8 | 0.017 | 0.034 | 0.025 | 0.000 | 0.000 | 0.004 |
C1 | 0.027 | 0.040 | 0.023 | 0.006 | 0.000 | 0.000 |
C11 | 0.039 | 0.034 | 0.027 | 0.000 | 0.000 | 0.004 |
C3 | 0.023 | 0.036 | 0.048 | 0.000 | 0.007 | 0.003 |
Geometric parameters (Å, º) top
I1—N2 | 2.181 (17) | C10—C9 | 1.383 (15) |
I1—N1 | 2.23 (2) | C10—C11 | 1.37 (2) |
S1—O1 | 1.433 (9) | C12—H12 | 0.9300 |
S1—N1 | 1.66 (2) | C12—C11 | 1.37 (2) |
S1—C5 | 1.745 (17) | C5—C6 | 1.396 (15) |
S1—O2 | 1.419 (11) | C6—C1 | 1.393 (14) |
N2—C12 | 1.359 (13) | C9—H9 | 0.9300 |
N2—C8 | 1.380 (19) | C9—C8 | 1.38 (2) |
O3—C7 | 1.21 (3) | C2—H2 | 0.9300 |
C7—N1 | 1.360 (15) | C2—C1 | 1.394 (16) |
C7—C6 | 1.47 (4) | C2—C3 | 1.383 (15) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.391 (16) | C1—H1 | 0.9300 |
C4—C3 | 1.387 (14) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N2—I1—N1 | 172.9 (5) | C4—C5—S1 | 127.5 (9) |
O1—S1—N1 | 110.8 (10) | C4—C5—C6 | 123.8 (14) |
O1—S1—C5 | 110.7 (6) | C6—C5—S1 | 108.5 (12) |
N1—S1—C5 | 94.8 (7) | C5—C6—C7 | 111.7 (12) |
O2—S1—O1 | 116.1 (5) | C1—C6—C7 | 130.3 (15) |
O2—S1—N1 | 110.0 (8) | C1—C6—C5 | 118.0 (16) |
O2—S1—C5 | 112.4 (9) | C10—C9—H9 | 121.8 |
C12—N2—I1 | 121.7 (14) | C8—C9—C10 | 116.4 (18) |
C12—N2—C8 | 116.7 (16) | C8—C9—H9 | 121.8 |
C8—N2—I1 | 121.1 (8) | C1—C2—H2 | 119.4 |
O3—C7—N1 | 123 (2) | C3—C2—H2 | 119.4 |
O3—C7—C6 | 124.0 (13) | C3—C2—C1 | 121.2 (15) |
N1—C7—C6 | 113 (2) | N2—C8—H8 | 117.6 |
C5—C4—H4 | 121.8 | C9—C8—N2 | 124.8 (13) |
C3—C4—H4 | 121.8 | C9—C8—H8 | 117.6 |
C3—C4—C5 | 116.5 (16) | C6—C1—C2 | 119.2 (15) |
C9—C10—H10 | 119.9 | C6—C1—H1 | 120.4 |
C11—C10—H10 | 119.9 | C2—C1—H1 | 120.4 |
C11—C10—C9 | 120.2 (18) | C10—C11—C12 | 121.0 (14) |
S1—N1—I1 | 115.1 (5) | C10—C11—H11 | 119.5 |
C7—N1—I1 | 132.1 (19) | C12—C11—H11 | 119.5 |
C7—N1—S1 | 112.1 (19) | C4—C3—H3 | 119.4 |
N2—C12—H12 | 119.6 | C2—C3—C4 | 121.3 (18) |
N2—C12—C11 | 120.9 (18) | C2—C3—H3 | 119.4 |
C11—C12—H12 | 119.6 | | |
| | | |
I1—N2—C12—C11 | 170.3 (10) | N1—C7—C6—C1 | −178.9 (13) |
I1—N2—C8—C9 | −171.9 (11) | C12—N2—C8—C9 | 1 (2) |
S1—C5—C6—C7 | 2.3 (15) | C5—S1—N1—I1 | −166.3 (6) |
S1—C5—C6—C1 | −177.3 (11) | C5—S1—N1—C7 | 5.5 (10) |
N2—C12—C11—C10 | 3 (2) | C5—C4—C3—C2 | −3 (2) |
O3—C7—N1—I1 | −11.3 (19) | C5—C6—C1—C2 | 0.3 (19) |
O3—C7—N1—S1 | 178.8 (12) | O2—S1—N1—I1 | 77.8 (8) |
O3—C7—C6—C5 | 177.8 (13) | O2—S1—N1—C7 | −110.4 (10) |
O3—C7—C6—C1 | −3 (3) | O2—S1—C5—C4 | −65.4 (14) |
O1—S1—N1—I1 | −52.0 (7) | O2—S1—C5—C6 | 109.6 (11) |
O1—S1—N1—C7 | 119.8 (10) | C6—C7—N1—I1 | 165.0 (11) |
O1—S1—C5—C4 | 66.3 (16) | C6—C7—N1—S1 | −5.0 (16) |
O1—S1—C5—C6 | −118.7 (11) | C9—C10—C11—C12 | −1 (2) |
C7—C6—C1—C2 | −179.1 (17) | C8—N2—C12—C11 | −2.2 (19) |
C4—C5—C6—C7 | 177.5 (15) | C1—C2—C3—C4 | 1 (2) |
C4—C5—C6—C1 | −2.0 (19) | C11—C10—C9—C8 | 0 (2) |
C10—C9—C8—N2 | 0 (2) | C3—C4—C5—S1 | 177.6 (10) |
N1—S1—C5—C4 | −179.4 (13) | C3—C4—C5—C6 | 3 (2) |
N1—S1—C5—C6 | −4.4 (9) | C3—C2—C1—C6 | 0 (2) |
N1—C7—C6—C5 | 1.6 (19) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 2.190 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.581 (13) Å | Cell parameters from 3433 reflections |
b = 7.2485 (14) Å | θ = 3.2–24.6° |
c = 12.220 (2) Å | µ = 2.90 mm−1 |
β = 89.447 (10)° | T = 296 K |
V = 2354.4 (13) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 590 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.047 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. | θmax = 23.2°, θmin = 1.8° |
Tmin = 0.461, Tmax = 0.563 | h = −11→10 |
8768 measured reflections | k = −8→8 |
687 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.014P)2 + 86.6837P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
687 reflections | Δρmax = 0.81 e Å−3 |
71 parameters | Δρmin = −0.43 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.27982 (10) | 0.39972 (12) | 0.47704 (7) | 0.0298 (12) | |
S1 | 0.4010 (4) | 0.4827 (5) | 0.4503 (3) | 0.036 (5) | |
N2 | 0.2162 (9) | 0.3899 (16) | 0.5897 (8) | 0.028 | |
O3 | 0.3275 (9) | 0.4005 (14) | 0.2005 (7) | 0.032 | |
O1 | 0.3924 (9) | 0.6392 (13) | 0.5180 (7) | 0.035 | |
C7 | 0.3580 (14) | 0.4373 (18) | 0.2677 (11) | 0.024 | |
C4 | 0.4885 (10) | 0.599 (2) | 0.3361 (11) | 0.035 | |
H4 | 0.5067 | 0.6134 | 0.4001 | 0.042* | |
C10 | 0.1367 (10) | 0.4216 (18) | 0.7385 (10) | 0.026 | |
H10 | 0.1106 | 0.4332 | 0.7895 | 0.031* | |
N1 | 0.3512 (11) | 0.4305 (15) | 0.3783 (9) | 0.025 | |
C12 | 0.2201 (12) | 0.3253 (18) | 0.6938 (10) | 0.031 | |
H12 | 0.2496 | 0.2663 | 0.7146 | 0.037* | |
C5 | 0.4388 (9) | 0.5419 (18) | 0.3360 (10) | 0.022 | |
O2 | 0.4195 (9) | 0.3245 (12) | 0.5048 (7) | 0.029 | |
C6 | 0.4108 (12) | 0.5051 (18) | 0.2433 (8) | 0.019 | |
C9 | 0.1298 (11) | 0.4814 (19) | 0.6327 (11) | 0.030 | |
H9 | 0.0992 | 0.5289 | 0.6097 | 0.036* | |
C2 | 0.4826 (9) | 0.600 (2) | 0.1387 (11) | 0.032 | |
H2 | 0.4982 | 0.6198 | 0.0713 | 0.038* | |
C8 | 0.1707 (10) | 0.467 (2) | 0.5622 (11) | 0.024 | |
H8 | 0.1673 | 0.5133 | 0.4916 | 0.029* | |
C1 | 0.4332 (9) | 0.536 (2) | 0.1423 (10) | 0.028 | |
H1 | 0.4156 | 0.5150 | 0.0781 | 0.034* | |
C11 | 0.1816 (10) | 0.3451 (18) | 0.7694 (11) | 0.028 | |
H11 | 0.1860 | 0.3065 | 0.8413 | 0.034* | |
C3 | 0.5090 (13) | 0.6335 (19) | 0.2340 (9) | 0.033 | |
H3 | 0.5414 | 0.6807 | 0.2289 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.036 (4) | 0.0253 (5) | 0.0284 (5) | 0.0001 (8) | 0.0020 (8) | 0.0012 (4) |
S1 | 0.061 (17) | 0.030 (2) | 0.0184 (18) | −0.005 (3) | 0.002 (3) | 0.0022 (15) |
N2 | 0.028 | 0.028 | 0.028 | 0.000 | 0.002 | 0.001 |
O3 | 0.025 | 0.043 | 0.027 | 0.000 | 0.000 | 0.000 |
O1 | 0.037 | 0.047 | 0.022 | 0.000 | 0.001 | 0.000 |
C7 | 0.023 | 0.026 | 0.023 | 0.003 | 0.000 | 0.000 |
C4 | 0.025 | 0.042 | 0.038 | 0.000 | 0.000 | 0.000 |
C10 | 0.025 | 0.029 | 0.024 | 0.000 | 0.009 | 0.000 |
N1 | 0.023 | 0.031 | 0.021 | 0.000 | 0.000 | 0.001 |
C12 | 0.039 | 0.025 | 0.029 | 0.000 | 0.000 | 0.003 |
C5 | 0.022 | 0.021 | 0.022 | 0.000 | 0.000 | 0.000 |
O2 | 0.026 | 0.033 | 0.027 | 0.000 | 0.000 | 0.009 |
C6 | 0.014 | 0.022 | 0.020 | 0.004 | 0.000 | 0.000 |
C9 | 0.024 | 0.034 | 0.033 | 0.012 | 0.000 | 0.000 |
C2 | 0.029 | 0.036 | 0.030 | 0.003 | 0.007 | 0.003 |
C8 | 0.016 | 0.032 | 0.024 | 0.000 | 0.000 | 0.003 |
C1 | 0.025 | 0.037 | 0.021 | 0.005 | 0.000 | 0.000 |
C11 | 0.033 | 0.029 | 0.023 | 0.000 | 0.000 | 0.003 |
C3 | 0.022 | 0.034 | 0.045 | 0.000 | 0.006 | 0.002 |
Geometric parameters (Å, º) top
I1—N2 | 2.17 (2) | C10—C9 | 1.378 (17) |
I1—N1 | 2.25 (2) | C10—C11 | 1.37 (2) |
S1—O1 | 1.421 (11) | C12—H12 | 0.9300 |
S1—N1 | 1.64 (3) | C12—C11 | 1.38 (3) |
S1—C5 | 1.77 (2) | C5—C6 | 1.387 (16) |
S1—O2 | 1.416 (13) | C6—C1 | 1.383 (15) |
N2—C12 | 1.360 (16) | C9—H9 | 0.9300 |
N2—C8 | 1.38 (2) | C9—C8 | 1.38 (3) |
O3—C7 | 1.19 (3) | C2—H2 | 0.9300 |
C7—N1 | 1.362 (18) | C2—C1 | 1.393 (17) |
C7—C6 | 1.51 (4) | C2—C3 | 1.387 (16) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.385 (17) | C1—H1 | 0.9300 |
C4—C3 | 1.378 (15) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N2—I1—N1 | 172.2 (6) | C4—C5—S1 | 127.5 (11) |
O1—S1—N1 | 111.7 (12) | C4—C5—C6 | 125.3 (17) |
O1—S1—C5 | 110.7 (8) | C6—C5—S1 | 107.1 (14) |
N1—S1—C5 | 95.0 (8) | C5—C6—C7 | 113.9 (13) |
O2—S1—O1 | 115.3 (6) | C1—C6—C7 | 128.2 (18) |
O2—S1—N1 | 110.6 (9) | C1—C6—C5 | 117.9 (19) |
O2—S1—C5 | 111.7 (10) | C10—C9—H9 | 121.6 |
C12—N2—I1 | 122.5 (16) | C10—C9—C8 | 117 (2) |
C12—N2—C8 | 116.4 (19) | C8—C9—H9 | 121.6 |
C8—N2—I1 | 120.8 (10) | C1—C2—H2 | 119.5 |
O3—C7—N1 | 126 (3) | C3—C2—H2 | 119.5 |
O3—C7—C6 | 125.0 (15) | C3—C2—C1 | 121.1 (17) |
N1—C7—C6 | 109 (2) | N2—C8—C9 | 124.3 (16) |
C5—C4—H4 | 122.5 | N2—C8—H8 | 117.8 |
C3—C4—H4 | 122.5 | C9—C8—H8 | 117.8 |
C3—C4—C5 | 115 (2) | C6—C1—C2 | 118.6 (18) |
C9—C10—H10 | 119.7 | C6—C1—H1 | 120.7 |
C11—C10—H10 | 119.7 | C2—C1—H1 | 120.7 |
C11—C10—C9 | 121 (2) | C10—C11—C12 | 120.0 (16) |
S1—N1—I1 | 114.5 (6) | C10—C11—H11 | 120.0 |
C7—N1—I1 | 130 (2) | C12—C11—H11 | 120.0 |
C7—N1—S1 | 115 (2) | C4—C3—C2 | 122 (2) |
N2—C12—H12 | 119.1 | C4—C3—H3 | 119.0 |
N2—C12—C11 | 122 (2) | C2—C3—H3 | 119.0 |
C11—C12—H12 | 119.1 | | |
| | | |
I1—N2—C12—C11 | 170.2 (13) | N1—C7—C6—C1 | −178.6 (15) |
I1—N2—C8—C9 | −174.1 (13) | C12—N2—C8—C9 | 0 (2) |
S1—C5—C6—C7 | 2.6 (17) | C5—S1—N1—I1 | −166.9 (7) |
S1—C5—C6—C1 | −178.3 (13) | C5—S1—N1—C7 | 4.6 (13) |
N2—C12—C11—C10 | 4 (2) | C5—C4—C3—C2 | −5 (2) |
O3—C7—N1—I1 | −12 (2) | C5—C6—C1—C2 | 1 (2) |
O3—C7—N1—S1 | 178.0 (15) | O2—S1—N1—I1 | 77.6 (10) |
O3—C7—C6—C5 | 178.8 (16) | O2—S1—N1—C7 | −110.9 (12) |
O3—C7—C6—C1 | 0 (3) | O2—S1—C5—C4 | −64.4 (17) |
O1—S1—N1—I1 | −52.3 (8) | O2—S1—C5—C6 | 110.5 (12) |
O1—S1—N1—C7 | 119.2 (12) | C6—C7—N1—I1 | 166.4 (12) |
O1—S1—C5—C4 | 65.6 (19) | C6—C7—N1—S1 | −3.6 (19) |
O1—S1—C5—C6 | −119.5 (13) | C9—C10—C11—C12 | −1 (2) |
C7—C6—C1—C2 | 179.8 (19) | C8—N2—C12—C11 | −3 (2) |
C4—C5—C6—C7 | 177.7 (18) | C1—C2—C3—C4 | 3 (3) |
C4—C5—C6—C1 | −3 (2) | C11—C10—C9—C8 | −3 (2) |
C10—C9—C8—N2 | 3 (2) | C3—C4—C5—S1 | 179.0 (12) |
N1—S1—C5—C4 | −178.9 (16) | C3—C4—C5—C6 | 5 (2) |
N1—S1—C5—C6 | −4.0 (11) | C3—C2—C1—C6 | −1 (3) |
N1—C7—C6—C5 | 0 (2) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 2.199 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.559 (12) Å | Cell parameters from 3772 reflections |
b = 7.2336 (13) Å | θ = 3.2–22.5° |
c = 12.209 (2) Å | µ = 2.91 mm−1 |
β = 89.462 (9)° | T = 296 K |
V = 2345.4 (12) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 580 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.046 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. | θmax = 23.3°, θmin = 1.8° |
Tmin = 0.461, Tmax = 0.563 | h = −10→10 |
8817 measured reflections | k = −8→8 |
675 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0196P)2 + 88.6924P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max < 0.001 |
675 reflections | Δρmax = 0.70 e Å−3 |
71 parameters | Δρmin = −0.41 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.27970 (10) | 0.39989 (12) | 0.47694 (7) | 0.0285 (13) | |
S1 | 0.4009 (4) | 0.4831 (5) | 0.4505 (3) | 0.033 (5) | |
N2 | 0.2172 (9) | 0.3892 (17) | 0.5889 (9) | 0.028 | |
O3 | 0.3273 (10) | 0.3998 (15) | 0.2000 (8) | 0.031 | |
O1 | 0.3927 (9) | 0.6392 (14) | 0.5177 (7) | 0.036 | |
C7 | 0.3585 (15) | 0.4365 (19) | 0.2674 (11) | 0.024 | |
C4 | 0.4890 (10) | 0.601 (2) | 0.3364 (12) | 0.037 | |
H4 | 0.5070 | 0.6190 | 0.4005 | 0.045* | |
C10 | 0.1366 (10) | 0.4203 (19) | 0.7394 (11) | 0.027 | |
H10 | 0.1102 | 0.4280 | 0.7898 | 0.032* | |
N1 | 0.3518 (12) | 0.4304 (16) | 0.3783 (9) | 0.026 | |
C12 | 0.2195 (12) | 0.3244 (19) | 0.6947 (10) | 0.029 | |
H12 | 0.2485 | 0.2620 | 0.7156 | 0.035* | |
C5 | 0.4397 (10) | 0.5412 (18) | 0.3359 (10) | 0.019 | |
O2 | 0.4195 (9) | 0.3233 (13) | 0.5048 (7) | 0.029 | |
C6 | 0.4119 (12) | 0.5057 (19) | 0.2432 (8) | 0.017 | |
C9 | 0.1306 (12) | 0.483 (2) | 0.6325 (11) | 0.033 | |
H9 | 0.1004 | 0.5345 | 0.6095 | 0.039* | |
C2 | 0.4832 (10) | 0.601 (2) | 0.1384 (11) | 0.034 | |
H2 | 0.4988 | 0.6234 | 0.0711 | 0.040* | |
C8 | 0.1704 (10) | 0.467 (2) | 0.5637 (11) | 0.021 | |
H8 | 0.1665 | 0.5127 | 0.4930 | 0.025* | |
C1 | 0.4343 (10) | 0.536 (2) | 0.1427 (10) | 0.027 | |
H1 | 0.4167 | 0.5138 | 0.0785 | 0.032* | |
C11 | 0.1827 (11) | 0.3454 (18) | 0.7693 (11) | 0.025 | |
H11 | 0.1880 | 0.3099 | 0.8415 | 0.030* | |
C3 | 0.5090 (13) | 0.6329 (19) | 0.2340 (9) | 0.031 | |
H3 | 0.5417 | 0.6782 | 0.2290 | 0.037* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.034 (4) | 0.0241 (5) | 0.0273 (5) | −0.0003 (8) | 0.0024 (8) | 0.0015 (4) |
S1 | 0.051 (18) | 0.032 (2) | 0.0174 (18) | −0.004 (3) | 0.004 (3) | 0.0023 (15) |
N2 | 0.028 | 0.028 | 0.028 | 0.000 | 0.002 | 0.001 |
O3 | 0.025 | 0.043 | 0.027 | 0.000 | 0.000 | 0.000 |
O1 | 0.037 | 0.048 | 0.022 | 0.000 | 0.001 | 0.000 |
C7 | 0.023 | 0.026 | 0.023 | 0.003 | 0.000 | 0.000 |
C4 | 0.027 | 0.044 | 0.040 | 0.000 | 0.000 | 0.000 |
C10 | 0.026 | 0.030 | 0.024 | 0.000 | 0.009 | 0.000 |
N1 | 0.023 | 0.031 | 0.022 | 0.000 | 0.000 | 0.001 |
C12 | 0.037 | 0.024 | 0.027 | 0.000 | 0.000 | 0.003 |
C5 | 0.019 | 0.019 | 0.019 | 0.000 | 0.000 | 0.000 |
O2 | 0.026 | 0.033 | 0.027 | 0.000 | 0.000 | 0.009 |
C6 | 0.013 | 0.020 | 0.019 | 0.003 | 0.000 | 0.000 |
C9 | 0.026 | 0.036 | 0.036 | 0.013 | 0.000 | 0.000 |
C2 | 0.031 | 0.038 | 0.032 | 0.003 | 0.008 | 0.004 |
C8 | 0.014 | 0.028 | 0.020 | 0.000 | 0.000 | 0.003 |
C1 | 0.024 | 0.036 | 0.020 | 0.005 | 0.000 | 0.000 |
C11 | 0.029 | 0.025 | 0.020 | 0.000 | 0.000 | 0.003 |
C3 | 0.020 | 0.031 | 0.042 | 0.000 | 0.006 | 0.002 |
Geometric parameters (Å, º) top
I1—N2 | 2.14 (2) | C10—C9 | 1.392 (18) |
I1—N1 | 2.26 (3) | C10—C11 | 1.39 (2) |
S1—O1 | 1.411 (11) | C12—H12 | 0.9300 |
S1—N1 | 1.63 (3) | C12—C11 | 1.34 (3) |
S1—C5 | 1.78 (2) | C5—C6 | 1.381 (16) |
S1—O2 | 1.422 (13) | C6—C1 | 1.377 (16) |
N2—C12 | 1.376 (16) | C9—H9 | 0.9300 |
N2—C8 | 1.40 (2) | C9—C8 | 1.35 (3) |
O3—C7 | 1.20 (3) | C2—H2 | 0.9300 |
C7—N1 | 1.365 (19) | C2—C1 | 1.383 (17) |
C7—C6 | 1.53 (5) | C2—C3 | 1.378 (16) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.379 (17) | C1—H1 | 0.9300 |
C4—C3 | 1.372 (16) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N2—I1—N1 | 171.9 (7) | C4—C5—S1 | 127.8 (11) |
O1—S1—N1 | 112.4 (12) | C4—C5—C6 | 125.3 (17) |
O1—S1—C5 | 110.7 (8) | C6—C5—S1 | 106.9 (14) |
O1—S1—O2 | 115.6 (6) | C5—C6—C7 | 113.9 (14) |
N1—S1—C5 | 95.2 (9) | C1—C6—C7 | 128.1 (18) |
O2—S1—N1 | 110.2 (9) | C1—C6—C5 | 118 (2) |
O2—S1—C5 | 111.0 (10) | C10—C9—H9 | 121.3 |
C12—N2—I1 | 124.7 (17) | C8—C9—C10 | 117 (2) |
C12—N2—C8 | 113 (2) | C8—C9—H9 | 121.3 |
C8—N2—I1 | 121.9 (10) | C1—C2—H2 | 120.1 |
O3—C7—N1 | 126 (3) | C3—C2—H2 | 120.1 |
O3—C7—C6 | 125.7 (16) | C3—C2—C1 | 119.9 (18) |
N1—C7—C6 | 108 (2) | N2—C8—H8 | 117.0 |
C5—C4—H4 | 123.0 | C9—C8—N2 | 126.1 (16) |
C3—C4—H4 | 123.0 | C9—C8—H8 | 117.0 |
C3—C4—C5 | 114 (2) | C6—C1—C2 | 119.1 (19) |
C9—C10—H10 | 120.6 | C6—C1—H1 | 120.5 |
C11—C10—H10 | 120.6 | C2—C1—H1 | 120.5 |
C11—C10—C9 | 119 (2) | C10—C11—H11 | 119.8 |
S1—N1—I1 | 114.4 (6) | C12—C11—C10 | 120.3 (17) |
C7—N1—I1 | 129 (2) | C12—C11—H11 | 119.8 |
C7—N1—S1 | 116 (2) | C4—C3—C2 | 124 (2) |
N2—C12—H12 | 118.0 | C4—C3—H3 | 118.2 |
C11—C12—N2 | 124 (2) | C2—C3—H3 | 118.2 |
C11—C12—H12 | 118.0 | | |
| | | |
I1—N2—C12—C11 | 168.7 (14) | N1—C7—C6—C1 | −178.6 (15) |
I1—N2—C8—C9 | −173.1 (14) | C12—N2—C8—C9 | 1 (2) |
S1—C5—C6—C7 | 1.7 (18) | C5—S1—N1—I1 | −167.2 (7) |
S1—C5—C6—C1 | −178.7 (13) | C5—S1—N1—C7 | 4.1 (13) |
N2—C12—C11—C10 | 7 (3) | C5—C4—C3—C2 | −2 (3) |
O3—C7—N1—I1 | −12 (2) | C5—C6—C1—C2 | 0 (2) |
O3—C7—N1—S1 | 178.7 (15) | O2—S1—N1—I1 | 78.2 (10) |
O3—C7—C6—C5 | 178.7 (17) | O2—S1—N1—C7 | −110.6 (13) |
O3—C7—C6—C1 | −1 (3) | O2—S1—C5—C4 | −66.2 (18) |
O1—S1—N1—I1 | −52.3 (8) | O2—S1—C5—C6 | 110.8 (13) |
O1—S1—N1—C7 | 118.9 (13) | C6—C7—N1—I1 | 166.2 (12) |
O1—S1—C5—C4 | 64 (2) | C6—C7—N1—S1 | −4 (2) |
O1—S1—C5—C6 | −119.5 (14) | C9—C10—C11—C12 | −4 (2) |
C7—C6—C1—C2 | 179 (2) | C8—N2—C12—C11 | −5 (2) |
C4—C5—C6—C7 | 178.8 (19) | C1—C2—C3—C4 | 1 (3) |
C4—C5—C6—C1 | −2 (2) | C11—C10—C9—C8 | 0 (2) |
C10—C9—C8—N2 | 2 (3) | C3—C4—C5—S1 | 179.2 (12) |
N1—S1—C5—C4 | 179.9 (17) | C3—C4—C5—C6 | 3 (3) |
N1—S1—C5—C6 | −3.2 (11) | C3—C2—C1—C6 | 0 (3) |
N1—C7—C6—C5 | 1 (2) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 2.232 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.482 (12) Å | Cell parameters from 3775 reflections |
b = 7.1755 (13) Å | θ = 3.2–22.9° |
c = 12.156 (2) Å | µ = 2.96 mm−1 |
β = 89.626 (10)° | T = 296 K |
V = 2309.9 (12) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 590 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.046 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. | θmax = 23.3°, θmin = 1.8° |
Tmin = 0.461, Tmax = 0.563 | h = −11→10 |
8506 measured reflections | k = −7→7 |
673 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + 65.621P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
673 reflections | Δρmax = 0.34 e Å−3 |
71 parameters | Δρmin = −0.33 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.27921 (9) | 0.40037 (11) | 0.47668 (7) | 0.0282 (11) | |
S1 | 0.4006 (3) | 0.4838 (4) | 0.4506 (2) | 0.021 (4) | |
N2 | 0.2154 (9) | 0.3911 (15) | 0.5892 (8) | 0.025 | |
O3 | 0.3278 (8) | 0.3983 (13) | 0.1977 (7) | 0.030 | |
O1 | 0.3921 (8) | 0.6432 (11) | 0.5177 (6) | 0.033 | |
C7 | 0.3590 (13) | 0.4383 (17) | 0.2652 (10) | 0.023 | |
C4 | 0.4886 (9) | 0.600 (2) | 0.3371 (10) | 0.031 | |
H4 | 0.5062 | 0.6167 | 0.4023 | 0.038* | |
C10 | 0.1351 (9) | 0.4232 (17) | 0.7410 (10) | 0.026 | |
H10 | 0.1091 | 0.4348 | 0.7923 | 0.031* | |
N1 | 0.3511 (10) | 0.4318 (13) | 0.3771 (8) | 0.022 | |
C12 | 0.2190 (11) | 0.3263 (16) | 0.6940 (9) | 0.025 | |
H12 | 0.2485 | 0.2661 | 0.7147 | 0.030* | |
C5 | 0.4390 (9) | 0.5417 (16) | 0.3350 (9) | 0.018 | |
O2 | 0.4196 (8) | 0.3238 (11) | 0.5060 (6) | 0.029 | |
C6 | 0.4111 (11) | 0.5048 (17) | 0.2423 (8) | 0.016 | |
C9 | 0.1292 (10) | 0.4831 (18) | 0.6325 (10) | 0.028 | |
H9 | 0.0987 | 0.5310 | 0.6081 | 0.033* | |
C2 | 0.4837 (9) | 0.599 (2) | 0.1396 (10) | 0.030 | |
H2 | 0.4994 | 0.6210 | 0.0722 | 0.036* | |
C8 | 0.1696 (9) | 0.4691 (17) | 0.5639 (10) | 0.019 | |
H8 | 0.1660 | 0.5167 | 0.4933 | 0.023* | |
C1 | 0.4345 (9) | 0.5353 (18) | 0.1418 (10) | 0.025 | |
H1 | 0.4173 | 0.5133 | 0.0766 | 0.030* | |
C11 | 0.1816 (9) | 0.3453 (16) | 0.7695 (10) | 0.024 | |
H11 | 0.1868 | 0.3059 | 0.8414 | 0.029* | |
C3 | 0.5101 (12) | 0.6309 (17) | 0.2352 (9) | 0.033 | |
H3 | 0.5432 | 0.6743 | 0.2308 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.035 (3) | 0.0239 (4) | 0.0254 (4) | 0.0004 (8) | 0.0024 (7) | 0.0018 (4) |
S1 | 0.015 (15) | 0.0295 (19) | 0.0173 (16) | −0.004 (3) | 0.003 (3) | 0.0019 (14) |
N2 | 0.026 | 0.025 | 0.025 | 0.000 | 0.001 | 0.001 |
O3 | 0.024 | 0.041 | 0.026 | 0.000 | 0.000 | 0.000 |
O1 | 0.034 | 0.044 | 0.020 | 0.000 | 0.001 | 0.000 |
C7 | 0.022 | 0.025 | 0.022 | 0.003 | 0.000 | 0.000 |
C4 | 0.023 | 0.037 | 0.034 | 0.000 | 0.000 | 0.000 |
C10 | 0.025 | 0.029 | 0.023 | 0.000 | 0.009 | 0.000 |
N1 | 0.020 | 0.027 | 0.019 | 0.000 | 0.000 | 0.001 |
C12 | 0.032 | 0.021 | 0.023 | 0.000 | 0.000 | 0.003 |
C5 | 0.018 | 0.018 | 0.018 | 0.000 | 0.000 | 0.000 |
O2 | 0.027 | 0.034 | 0.027 | 0.000 | 0.000 | 0.009 |
C6 | 0.012 | 0.019 | 0.018 | 0.003 | 0.000 | 0.000 |
C9 | 0.022 | 0.031 | 0.030 | 0.011 | 0.000 | 0.000 |
C2 | 0.028 | 0.034 | 0.029 | 0.002 | 0.007 | 0.003 |
C8 | 0.013 | 0.026 | 0.019 | 0.000 | 0.000 | 0.003 |
C1 | 0.023 | 0.033 | 0.019 | 0.005 | 0.000 | 0.000 |
C11 | 0.028 | 0.024 | 0.019 | 0.000 | 0.000 | 0.003 |
C3 | 0.021 | 0.034 | 0.045 | 0.000 | 0.006 | 0.002 |
Geometric parameters (Å, º) top
I1—N2 | 2.168 (19) | C10—C9 | 1.397 (16) |
I1—N1 | 2.26 (2) | C10—C11 | 1.40 (2) |
S1—O1 | 1.422 (9) | C12—H12 | 0.9300 |
S1—N1 | 1.63 (2) | C12—C11 | 1.35 (3) |
S1—C5 | 1.778 (18) | C5—C6 | 1.378 (15) |
S1—O2 | 1.424 (12) | C6—C1 | 1.382 (15) |
N2—C12 | 1.360 (14) | C9—H9 | 0.9300 |
N2—C8 | 1.37 (2) | C9—C8 | 1.36 (3) |
O3—C7 | 1.20 (3) | C2—H2 | 0.9300 |
C7—N1 | 1.375 (17) | C2—C1 | 1.382 (17) |
C7—C6 | 1.49 (4) | C2—C3 | 1.379 (16) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.378 (16) | C1—H1 | 0.9300 |
C4—C3 | 1.379 (15) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N2—I1—N1 | 172.3 (6) | C4—C5—S1 | 126.6 (10) |
O1—S1—N1 | 111.8 (10) | C4—C5—C6 | 126.1 (15) |
O1—S1—C5 | 110.7 (7) | C6—C5—S1 | 107.2 (13) |
O1—S1—O2 | 115.6 (5) | C5—C6—C7 | 114.2 (12) |
N1—S1—C5 | 94.5 (8) | C5—C6—C1 | 117.0 (18) |
O2—S1—N1 | 111.2 (8) | C1—C6—C7 | 128.8 (17) |
O2—S1—C5 | 111.2 (9) | C10—C9—H9 | 121.1 |
C12—N2—I1 | 122.9 (15) | C8—C9—C10 | 117.7 (19) |
C12—N2—C8 | 114.5 (18) | C8—C9—H9 | 121.1 |
C8—N2—I1 | 122.2 (9) | C1—C2—H2 | 119.2 |
O3—C7—N1 | 124 (3) | C3—C2—H2 | 119.2 |
O3—C7—C6 | 126.1 (14) | C3—C2—C1 | 121.5 (16) |
N1—C7—C6 | 109 (2) | N2—C8—H8 | 117.0 |
C5—C4—H4 | 122.5 | C9—C8—N2 | 126.0 (15) |
C5—C4—C3 | 114.9 (18) | C9—C8—H8 | 117.0 |
C3—C4—H4 | 122.5 | C6—C1—H1 | 120.5 |
C9—C10—H10 | 121.3 | C2—C1—C6 | 119.0 (17) |
C11—C10—H10 | 121.3 | C2—C1—H1 | 120.5 |
C11—C10—C9 | 117.5 (19) | C10—C11—H11 | 119.6 |
S1—N1—I1 | 113.9 (5) | C12—C11—C10 | 120.9 (15) |
C7—N1—I1 | 131 (2) | C12—C11—H11 | 119.6 |
C7—N1—S1 | 115 (2) | C4—C3—C2 | 121 (2) |
N2—C12—H12 | 118.4 | C4—C3—H3 | 119.3 |
C11—C12—N2 | 123.1 (19) | C2—C3—H3 | 119.3 |
C11—C12—H12 | 118.4 | | |
| | | |
I1—N2—C12—C11 | 169.9 (12) | N1—C7—C6—C1 | −178.6 (14) |
I1—N2—C8—C9 | −174.2 (12) | C12—N2—C8—C9 | −1 (2) |
S1—C5—C6—C7 | 2.3 (16) | C5—S1—N1—I1 | −167.6 (6) |
S1—C5—C6—C1 | −178.3 (11) | C5—S1—N1—C7 | 4.5 (12) |
N2—C12—C11—C10 | 4 (2) | C5—C4—C3—C2 | −2 (2) |
O3—C7—N1—I1 | −12 (2) | C5—C6—C1—C2 | 0 (2) |
O3—C7—N1—S1 | 177.2 (14) | O2—S1—N1—I1 | 77.7 (9) |
O3—C7—C6—C5 | 179.7 (15) | O2—S1—N1—C7 | −110.2 (11) |
O3—C7—C6—C1 | 0 (3) | O2—S1—C5—C4 | −64.8 (15) |
O1—S1—N1—I1 | −53.2 (7) | O2—S1—C5—C6 | 110.9 (11) |
O1—S1—N1—C7 | 118.9 (11) | C6—C7—N1—I1 | 166.7 (11) |
O1—S1—C5—C4 | 65.1 (17) | C6—C7—N1—S1 | −3.7 (18) |
O1—S1—C5—C6 | −119.2 (12) | C9—C10—C11—C12 | −1 (2) |
C7—C6—C1—C2 | 179.7 (18) | C8—N2—C12—C11 | −3 (2) |
C4—C5—C6—C7 | 178.1 (17) | C1—C2—C3—C4 | 0 (2) |
C4—C5—C6—C1 | −2 (2) | C11—C10—C9—C8 | −3 (2) |
C10—C9—C8—N2 | 4 (2) | C3—C4—C5—S1 | 178.3 (10) |
N1—S1—C5—C4 | −179.6 (14) | C3—C4—C5—C6 | 3 (2) |
N1—S1—C5—C6 | −3.8 (10) | C3—C2—C1—C6 | 1 (2) |
N1—C7—C6—C5 | 1 (2) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 2.309 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.304 (11) Å | Cell parameters from 4330 reflections |
b = 7.0512 (11) Å | θ = 3.3–24.5° |
c = 12.042 (2) Å | µ = 3.06 mm−1 |
β = 89.932 (9)° | T = 296 K |
V = 2233.5 (11) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 590 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.040 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. | θmax = 23.2°, θmin = 1.9° |
Tmin = 0.461, Tmax = 0.563 | h = −11→10 |
8569 measured reflections | k = −7→7 |
656 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.020 | H-atom parameters constrained |
wR(F2) = 0.038 | w = 1/[σ2(Fo2) + (0.0102P)2 + 7.7918P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
656 reflections | Δρmax = 0.22 e Å−3 |
71 parameters | Δρmin = −0.22 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.27803 (5) | 0.40216 (5) | 0.47608 (3) | 0.0270 (5) | |
S1 | 0.39946 (15) | 0.4869 (2) | 0.45071 (12) | 0.025 (2) | |
N2 | 0.2121 (5) | 0.3927 (7) | 0.5911 (4) | 0.021 | |
O3 | 0.3274 (4) | 0.3953 (6) | 0.1941 (3) | 0.026 | |
O1 | 0.3908 (4) | 0.6506 (5) | 0.5176 (3) | 0.029 | |
C7 | 0.3589 (7) | 0.4402 (8) | 0.2627 (5) | 0.020 | |
C4 | 0.4879 (5) | 0.6001 (10) | 0.3392 (5) | 0.025 | |
H4 | 0.5051 | 0.6185 | 0.4059 | 0.030* | |
C10 | 0.1345 (5) | 0.4229 (8) | 0.7438 (5) | 0.024 | |
H10 | 0.1084 | 0.4334 | 0.7956 | 0.029* | |
N1 | 0.3498 (5) | 0.4324 (7) | 0.3763 (4) | 0.020 | |
C12 | 0.2207 (5) | 0.3271 (8) | 0.6956 (4) | 0.029 | |
H12 | 0.2518 | 0.2743 | 0.7154 | 0.035* | |
C5 | 0.4381 (5) | 0.5402 (8) | 0.3377 (5) | 0.019 | |
O2 | 0.4175 (4) | 0.3249 (5) | 0.5097 (3) | 0.026 | |
C6 | 0.4113 (6) | 0.5038 (9) | 0.2408 (4) | 0.017 | |
C9 | 0.1282 (5) | 0.4872 (8) | 0.6358 (4) | 0.024 | |
H9 | 0.0975 | 0.5401 | 0.6131 | 0.028* | |
C2 | 0.4858 (5) | 0.5974 (10) | 0.1400 (5) | 0.027 | |
H2 | 0.5024 | 0.6159 | 0.0726 | 0.032* | |
C8 | 0.1681 (5) | 0.4712 (9) | 0.5631 (5) | 0.019 | |
H8 | 0.1641 | 0.5172 | 0.4913 | 0.023* | |
C1 | 0.4358 (5) | 0.5357 (9) | 0.1405 (5) | 0.022 | |
H1 | 0.4188 | 0.5158 | 0.0739 | 0.027* | |
C11 | 0.1810 (5) | 0.3424 (8) | 0.7721 (5) | 0.022 | |
H11 | 0.1857 | 0.2974 | 0.8439 | 0.027* | |
C3 | 0.5117 (6) | 0.6320 (8) | 0.2384 (5) | 0.030 | |
H3 | 0.5450 | 0.6766 | 0.2366 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0364 (16) | 0.0241 (2) | 0.0206 (2) | −0.0014 (4) | 0.0023 (4) | 0.00113 (19) |
S1 | 0.032 (7) | 0.0262 (9) | 0.0170 (8) | −0.0010 (14) | 0.0020 (14) | 0.0005 (7) |
N2 | 0.022 | 0.021 | 0.021 | 0.000 | 0.001 | 0.001 |
O3 | 0.020 | 0.035 | 0.022 | 0.000 | 0.000 | 0.000 |
O1 | 0.030 | 0.039 | 0.018 | 0.000 | 0.001 | 0.000 |
C7 | 0.019 | 0.022 | 0.019 | 0.003 | 0.000 | 0.000 |
C4 | 0.018 | 0.029 | 0.027 | 0.000 | 0.000 | 0.000 |
C10 | 0.023 | 0.027 | 0.022 | 0.000 | 0.008 | 0.000 |
N1 | 0.018 | 0.024 | 0.017 | 0.000 | 0.000 | 0.001 |
C12 | 0.036 | 0.024 | 0.027 | 0.000 | 0.000 | 0.003 |
C5 | 0.020 | 0.019 | 0.019 | 0.000 | 0.000 | 0.000 |
O2 | 0.024 | 0.030 | 0.024 | 0.000 | 0.000 | 0.008 |
C6 | 0.013 | 0.020 | 0.019 | 0.003 | 0.000 | 0.000 |
C9 | 0.019 | 0.026 | 0.026 | 0.010 | 0.000 | 0.000 |
C2 | 0.025 | 0.030 | 0.025 | 0.002 | 0.006 | 0.003 |
C8 | 0.013 | 0.026 | 0.019 | 0.000 | 0.000 | 0.003 |
C1 | 0.020 | 0.030 | 0.017 | 0.004 | 0.000 | 0.000 |
C11 | 0.026 | 0.023 | 0.018 | 0.000 | 0.000 | 0.003 |
C3 | 0.019 | 0.030 | 0.040 | 0.000 | 0.006 | 0.002 |
Geometric parameters (Å, º) top
I1—N2 | 2.218 (9) | C10—C9 | 1.387 (8) |
I1—N1 | 2.248 (11) | C10—C11 | 1.391 (14) |
S1—O1 | 1.425 (4) | C12—H12 | 0.9300 |
S1—N1 | 1.630 (12) | C12—C11 | 1.397 (14) |
S1—C5 | 1.739 (9) | C5—C6 | 1.388 (10) |
S1—O2 | 1.427 (5) | C6—C1 | 1.387 (10) |
N2—C12 | 1.360 (7) | C9—H9 | 0.9300 |
N2—C8 | 1.329 (13) | C9—C8 | 1.369 (13) |
O3—C7 | 1.213 (15) | C2—H2 | 0.9300 |
C7—N1 | 1.389 (8) | C2—C1 | 1.386 (13) |
C7—C6 | 1.47 (2) | C2—C3 | 1.389 (11) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.378 (12) | C1—H1 | 0.9300 |
C4—C3 | 1.383 (9) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N2—I1—N1 | 172.8 (3) | C4—C5—S1 | 127.7 (6) |
O1—S1—N1 | 112.0 (5) | C4—C5—C6 | 123.6 (8) |
O1—S1—C5 | 111.1 (3) | C6—C5—S1 | 108.7 (8) |
O1—S1—O2 | 114.9 (2) | C5—C6—C7 | 112.5 (7) |
N1—S1—C5 | 95.0 (4) | C1—C6—C7 | 129.8 (9) |
O2—S1—N1 | 110.6 (4) | C1—C6—C5 | 117.7 (10) |
O2—S1—C5 | 111.6 (5) | C10—C9—H9 | 120.7 |
C12—N2—I1 | 117.2 (8) | C8—C9—C10 | 118.7 (10) |
C8—N2—I1 | 120.7 (5) | C8—C9—H9 | 120.7 |
C8—N2—C12 | 121.5 (9) | C1—C2—H2 | 119.4 |
O3—C7—N1 | 123.0 (13) | C1—C2—C3 | 121.2 (8) |
O3—C7—C6 | 126.6 (7) | C3—C2—H2 | 119.4 |
N1—C7—C6 | 110.3 (11) | N2—C8—C9 | 122.7 (7) |
C5—C4—H4 | 121.1 | N2—C8—H8 | 118.7 |
C5—C4—C3 | 117.9 (9) | C9—C8—H8 | 118.7 |
C3—C4—H4 | 121.1 | C6—C1—H1 | 120.1 |
C9—C10—H10 | 121.0 | C2—C1—C6 | 119.7 (9) |
C9—C10—C11 | 117.9 (9) | C2—C1—H1 | 120.1 |
C11—C10—H10 | 121.0 | C10—C11—C12 | 121.9 (7) |
S1—N1—I1 | 113.7 (3) | C10—C11—H11 | 119.1 |
C7—N1—I1 | 132.3 (11) | C12—C11—H11 | 119.1 |
C7—N1—S1 | 113.3 (11) | C4—C3—C2 | 119.9 (11) |
N2—C12—H12 | 121.4 | C4—C3—H3 | 120.0 |
N2—C12—C11 | 117.3 (10) | C2—C3—H3 | 120.0 |
C11—C12—H12 | 121.4 | | |
| | | |
I1—N2—C12—C11 | 172.5 (5) | N1—C7—C6—C1 | −178.3 (7) |
I1—N2—C8—C9 | −172.7 (6) | C12—N2—C8—C9 | −1.7 (12) |
S1—C5—C6—C7 | 2.3 (8) | C5—S1—N1—I1 | −168.4 (3) |
S1—C5—C6—C1 | −179.4 (6) | C5—S1—N1—C7 | 3.0 (6) |
N2—C12—C11—C10 | −0.7 (11) | C5—C4—C3—C2 | −2.2 (11) |
O3—C7—N1—I1 | −14.4 (11) | C5—C6—C1—C2 | 1.5 (11) |
O3—C7—N1—S1 | 176.2 (7) | O2—S1—N1—I1 | 76.3 (4) |
O3—C7—C6—C5 | −178.5 (7) | O2—S1—N1—C7 | −112.3 (5) |
O3—C7—C6—C1 | 3.4 (16) | O2—S1—C5—C4 | −65.6 (8) |
O1—S1—N1—I1 | −53.2 (3) | O2—S1—C5—C6 | 111.5 (6) |
O1—S1—N1—C7 | 118.2 (5) | C6—C7—N1—I1 | 167.2 (6) |
O1—S1—C5—C4 | 64.0 (9) | C6—C7—N1—S1 | −2.1 (9) |
O1—S1—C5—C6 | −118.9 (6) | C9—C10—C11—C12 | 0.6 (11) |
C7—C6—C1—C2 | 179.5 (9) | C8—N2—C12—C11 | 1.2 (11) |
C4—C5—C6—C7 | 179.5 (8) | C1—C2—C3—C4 | 1.7 (11) |
C4—C5—C6—C1 | −2.1 (12) | C11—C10—C9—C8 | −1.0 (11) |
C10—C9—C8—N2 | 1.6 (12) | C3—C4—C5—S1 | 179.1 (5) |
N1—S1—C5—C4 | 179.8 (8) | C3—C4—C5—C6 | 2.4 (12) |
N1—S1—C5—C6 | −3.1 (5) | C3—C2—C1—C6 | −1.4 (12) |
N1—C7—C6—C5 | −0.2 (10) | | |
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 2.385 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.020 (12) Å | Cell parameters from 3659 reflections |
b = 6.9618 (13) Å | θ = 3.3–23.1° |
c = 11.937 (2) Å | µ = 3.16 mm−1 |
β = 89.476 (10)° | T = 296 K |
V = 2162.3 (11) Å3 | Plate, colourless |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 553 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.046 |
Absorption correction: empirical (using intensity measurements) SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0628 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8928.
The λ/2 correction factor is Not present. | θmax = 23.4°, θmin = 1.9° |
Tmin = 0.502, Tmax = 0.563 | h = −11→11 |
7793 measured reflections | k = −7→7 |
635 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.049 | w = 1/[σ2(Fo2) + 18.6464P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max < 0.001 |
635 reflections | Δρmax = 0.29 e Å−3 |
71 parameters | Δρmin = −0.31 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.27674 (7) | 0.40504 (7) | 0.47602 (5) | 0.0274 (7) | |
S1 | 0.3978 (2) | 0.4904 (3) | 0.45065 (17) | 0.025 (3) | |
N2 | 0.2126 (6) | 0.3969 (11) | 0.5922 (5) | 0.022 | |
O3 | 0.3261 (5) | 0.3908 (9) | 0.1901 (4) | 0.025 | |
O1 | 0.3892 (5) | 0.6572 (8) | 0.5165 (4) | 0.029 | |
C7 | 0.3587 (9) | 0.4404 (12) | 0.2607 (7) | 0.022 | |
C4 | 0.4880 (7) | 0.6036 (15) | 0.3427 (7) | 0.027 | |
H4 | 0.5042 | 0.6238 | 0.4108 | 0.032* | |
C10 | 0.1339 (7) | 0.4246 (12) | 0.7459 (7) | 0.020 | |
H10 | 0.1074 | 0.4345 | 0.7985 | 0.024* | |
N1 | 0.3494 (7) | 0.4354 (10) | 0.3742 (5) | 0.019 | |
C12 | 0.2192 (7) | 0.3274 (11) | 0.6981 (6) | 0.027 | |
H12 | 0.2502 | 0.2705 | 0.7181 | 0.033* | |
C5 | 0.4380 (7) | 0.5425 (12) | 0.3369 (6) | 0.019 | |
O2 | 0.4163 (5) | 0.3261 (7) | 0.5120 (4) | 0.025 | |
C6 | 0.4116 (8) | 0.5040 (13) | 0.2394 (6) | 0.016 | |
C9 | 0.1269 (7) | 0.4926 (13) | 0.6390 (7) | 0.026 | |
H9 | 0.0959 | 0.5465 | 0.6170 | 0.032* | |
C2 | 0.4880 (7) | 0.5973 (14) | 0.1415 (7) | 0.023 | |
H2 | 0.5058 | 0.6154 | 0.0743 | 0.028* | |
C8 | 0.1674 (7) | 0.4773 (12) | 0.5666 (7) | 0.019 | |
H8 | 0.1635 | 0.5260 | 0.4947 | 0.022* | |
C1 | 0.4375 (6) | 0.5345 (13) | 0.1392 (7) | 0.024 | |
H1 | 0.4212 | 0.5132 | 0.0713 | 0.028* | |
C11 | 0.1795 (7) | 0.3426 (12) | 0.7751 (7) | 0.023 | |
H11 | 0.1838 | 0.2965 | 0.8475 | 0.027* | |
C3 | 0.5127 (8) | 0.6335 (12) | 0.2413 (6) | 0.030 | |
H3 | 0.5464 | 0.6786 | 0.2402 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.039 (2) | 0.0234 (3) | 0.0197 (3) | −0.0007 (6) | 0.0044 (5) | 0.0011 (3) |
S1 | 0.034 (10) | 0.0236 (13) | 0.0171 (11) | 0.001 (2) | 0.0051 (19) | 0.0010 (10) |
N2 | 0.022 | 0.022 | 0.022 | 0.000 | 0.001 | 0.001 |
O3 | 0.020 | 0.034 | 0.021 | 0.000 | 0.000 | 0.000 |
O1 | 0.030 | 0.039 | 0.018 | 0.000 | 0.001 | 0.000 |
C7 | 0.021 | 0.023 | 0.021 | 0.003 | 0.000 | 0.000 |
C4 | 0.020 | 0.032 | 0.029 | 0.000 | 0.000 | 0.000 |
C10 | 0.019 | 0.022 | 0.018 | 0.000 | 0.007 | 0.000 |
N1 | 0.017 | 0.023 | 0.016 | 0.000 | 0.000 | 0.001 |
C12 | 0.034 | 0.022 | 0.025 | 0.000 | 0.000 | 0.003 |
C5 | 0.019 | 0.019 | 0.019 | 0.000 | 0.000 | 0.000 |
O2 | 0.023 | 0.029 | 0.024 | 0.000 | 0.000 | 0.008 |
C6 | 0.012 | 0.019 | 0.018 | 0.003 | 0.000 | 0.000 |
C9 | 0.021 | 0.029 | 0.029 | 0.011 | 0.000 | 0.000 |
C2 | 0.021 | 0.026 | 0.022 | 0.002 | 0.005 | 0.002 |
C8 | 0.013 | 0.025 | 0.019 | 0.000 | 0.000 | 0.003 |
C1 | 0.021 | 0.032 | 0.018 | 0.005 | 0.000 | 0.000 |
C11 | 0.027 | 0.023 | 0.018 | 0.000 | 0.000 | 0.003 |
C3 | 0.019 | 0.030 | 0.040 | 0.000 | 0.006 | 0.002 |
Geometric parameters (Å, º) top
I1—N2 | 2.162 (13) | C10—C9 | 1.375 (11) |
I1—N1 | 2.249 (16) | C10—C11 | 1.366 (17) |
S1—O1 | 1.419 (6) | C12—H12 | 0.9300 |
S1—N1 | 1.606 (16) | C12—C11 | 1.382 (18) |
S1—C5 | 1.746 (13) | C5—C6 | 1.382 (12) |
S1—O2 | 1.444 (8) | C6—C1 | 1.384 (12) |
N2—C12 | 1.366 (9) | C9—H9 | 0.9300 |
N2—C8 | 1.338 (16) | C9—C8 | 1.361 (18) |
O3—C7 | 1.25 (2) | C2—H2 | 0.9300 |
C7—N1 | 1.375 (12) | C2—C1 | 1.387 (14) |
C7—C6 | 1.47 (3) | C2—C3 | 1.381 (13) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.370 (14) | C1—H1 | 0.9300 |
C4—C3 | 1.382 (11) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N2—I1—N1 | 172.0 (4) | C4—C5—S1 | 126.0 (7) |
O1—S1—N1 | 112.9 (7) | C4—C5—C6 | 125.6 (11) |
O1—S1—C5 | 110.6 (5) | C6—C5—S1 | 108.3 (10) |
O1—S1—O2 | 114.8 (3) | C5—C6—C7 | 112.7 (9) |
N1—S1—C5 | 94.3 (6) | C5—C6—C1 | 117.1 (14) |
O2—S1—N1 | 111.5 (5) | C1—C6—C7 | 130.1 (13) |
O2—S1—C5 | 111.0 (7) | C10—C9—H9 | 121.5 |
C12—N2—I1 | 119.9 (11) | C8—C9—C10 | 117.0 (13) |
C8—N2—I1 | 121.1 (6) | C8—C9—H9 | 121.5 |
C8—N2—C12 | 118.6 (12) | C1—C2—H2 | 119.2 |
O3—C7—N1 | 122.9 (19) | C3—C2—H2 | 119.2 |
O3—C7—C6 | 127.6 (9) | C3—C2—C1 | 121.5 (11) |
N1—C7—C6 | 109.5 (15) | N2—C8—C9 | 124.4 (10) |
C5—C4—H4 | 122.1 | N2—C8—H8 | 117.8 |
C5—C4—C3 | 115.9 (13) | C9—C8—H8 | 117.8 |
C3—C4—H4 | 122.1 | C6—C1—C2 | 119.0 (12) |
C9—C10—H10 | 119.9 | C6—C1—H1 | 120.5 |
C11—C10—H10 | 119.9 | C2—C1—H1 | 120.5 |
C11—C10—C9 | 120.2 (13) | C10—C11—C12 | 120.6 (10) |
S1—N1—I1 | 112.0 (4) | C10—C11—H11 | 119.7 |
C7—N1—I1 | 132.4 (15) | C12—C11—H11 | 119.7 |
C7—N1—S1 | 115.0 (15) | C4—C3—H3 | 119.6 |
N2—C12—H12 | 120.4 | C2—C3—C4 | 120.8 (14) |
N2—C12—C11 | 119.2 (13) | C2—C3—H3 | 119.6 |
C11—C12—H12 | 120.4 | | |
| | | |
I1—N2—C12—C11 | 172.9 (7) | N1—C7—C6—C1 | −178.4 (10) |
I1—N2—C8—C9 | −174.0 (8) | C12—N2—C8—C9 | −1.0 (17) |
S1—C5—C6—C7 | 2.2 (12) | C5—S1—N1—I1 | −169.0 (4) |
S1—C5—C6—C1 | −179.3 (8) | C5—S1—N1—C7 | 3.1 (8) |
N2—C12—C11—C10 | 0.5 (15) | C5—C4—C3—C2 | −1.8 (15) |
O3—C7—N1—I1 | −14.2 (15) | C5—C6—C1—C2 | 1.3 (15) |
O3—C7—N1—S1 | 175.8 (9) | O2—S1—N1—I1 | 76.4 (6) |
O3—C7—C6—C5 | −178.1 (10) | O2—S1—N1—C7 | −111.5 (8) |
O3—C7—C6—C1 | 4 (2) | O2—S1—C5—C4 | −65.6 (11) |
O1—S1—N1—I1 | −54.5 (5) | O2—S1—C5—C6 | 112.0 (8) |
O1—S1—N1—C7 | 117.6 (8) | C6—C7—N1—I1 | 167.8 (8) |
O1—S1—C5—C4 | 63.0 (12) | C6—C7—N1—S1 | −2.2 (13) |
O1—S1—C5—C6 | −119.5 (8) | C9—C10—C11—C12 | 0.2 (16) |
C7—C6—C1—C2 | 179.4 (13) | C8—N2—C12—C11 | −0.1 (15) |
C4—C5—C6—C7 | 179.8 (12) | C1—C2—C3—C4 | 1.6 (16) |
C4—C5—C6—C1 | −1.7 (17) | C11—C10—C9—C8 | −1.3 (16) |
C10—C9—C8—N2 | 1.8 (17) | C3—C4—C5—S1 | 179.1 (7) |
N1—S1—C5—C4 | 179.4 (11) | C3—C4—C5—C6 | 1.9 (17) |
N1—S1—C5—C6 | −3.0 (8) | C3—C2—C1—C6 | −1.3 (17) |
N1—C7—C6—C5 | −0.2 (15) | | |
(NISac_Py_crystal_2_RTP)
top
Crystal data top
C12H9IN2O3S | F(000) = 1504 |
Mr = 388.17 | Dx = 1.918 Mg m−3 |
Monoclinic, ¯B2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 27.272 (5) Å | Cell parameters from 9316 reflections |
b = 7.8156 (9) Å | θ = 3.0–25.7° |
c = 12.6155 (16) Å | µ = 2.54 mm−1 |
β = 88.703 (3)° | T = 296 K |
V = 2688.3 (7) Å3 | Plate, orange |
Z = 8 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 2670 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.049 |
Absorption correction: numerical SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0713 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.8904.
The λ/2 correction factor is Not present. | θmax = 26.4°, θmin = 1.8° |
Tmin = 0.566, Tmax = 0.636 | h = −34→34 |
67239 measured reflections | k = −9→9 |
2738 independent reflections | l = −15→15 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.155 | w = 1/[σ2(Fo2) + (0.0572P)2 + 59.271P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max = 0.001 |
2738 reflections | Δρmax = 2.49 e Å−3 |
173 parameters | Δρmin = −1.41 e Å−3 |
18 restraints | |
Special details top
Geometry. 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.28456 (2) | 0.39789 (7) | 0.47960 (4) | 0.0384 (2) | |
S1 | 0.40403 (8) | 0.4726 (3) | 0.44963 (16) | 0.0397 (5) | |
N2 | 0.2160 (3) | 0.3816 (9) | 0.5873 (6) | 0.0422 (17) | |
O3 | 0.3281 (2) | 0.4086 (10) | 0.2149 (5) | 0.0548 (18) | |
O1 | 0.3959 (3) | 0.6143 (11) | 0.5179 (6) | 0.064 (2) | |
C7 | 0.3601 (3) | 0.4393 (12) | 0.2768 (7) | 0.0384 (18) | |
C4 | 0.4855 (3) | 0.5933 (13) | 0.3284 (7) | 0.050 (2) | |
H4 | 0.5039 | 0.6112 | 0.3886 | 0.060* | |
C10 | 0.1392 (4) | 0.4133 (13) | 0.7307 (7) | 0.054 (2) | |
H10 | 0.1132 | 0.4239 | 0.7793 | 0.064* | |
N1 | 0.3549 (3) | 0.4259 (10) | 0.3854 (6) | 0.0421 (17) | |
C12 | 0.2198 (4) | 0.3229 (13) | 0.6860 (7) | 0.051 (2) | |
H12 | 0.2488 | 0.2695 | 0.7054 | 0.061* | |
C5 | 0.4383 (3) | 0.5312 (11) | 0.3358 (6) | 0.0337 (16) | |
O2 | 0.4245 (3) | 0.3237 (10) | 0.4954 (6) | 0.0580 (18) | |
C6 | 0.4104 (3) | 0.5007 (11) | 0.2480 (6) | 0.0344 (17) | |
C9 | 0.1347 (3) | 0.4722 (14) | 0.6283 (8) | 0.051 (2) | |
H9 | 0.1056 | 0.5215 | 0.6065 | 0.062* | |
C2 | 0.4769 (3) | 0.5993 (14) | 0.1392 (8) | 0.056 (3) | |
H2 | 0.4902 | 0.6234 | 0.0723 | 0.067* | |
C8 | 0.1742 (3) | 0.4566 (12) | 0.5592 (6) | 0.0375 (18) | |
H8 | 0.1717 | 0.4996 | 0.4908 | 0.045* | |
C1 | 0.4300 (3) | 0.5352 (14) | 0.1490 (7) | 0.050 (2) | |
H1 | 0.4117 | 0.5154 | 0.0889 | 0.060* | |
C11 | 0.1822 (4) | 0.3391 (13) | 0.7598 (8) | 0.049 (2) | |
H11 | 0.1860 | 0.3000 | 0.8288 | 0.059* | |
C3 | 0.5045 (4) | 0.6281 (14) | 0.2284 (7) | 0.054 (3) | |
H3 | 0.5361 | 0.6714 | 0.2207 | 0.065* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0310 (3) | 0.0415 (3) | 0.0427 (3) | −0.0016 (2) | 0.0008 (2) | 0.0009 (2) |
S1 | 0.0350 (10) | 0.0547 (13) | 0.0296 (9) | −0.0075 (9) | −0.0075 (8) | 0.0025 (9) |
N2 | 0.044 (4) | 0.039 (4) | 0.043 (4) | −0.004 (3) | 0.001 (3) | 0.006 (3) |
O3 | 0.043 (4) | 0.077 (5) | 0.045 (4) | −0.014 (3) | −0.012 (3) | −0.007 (3) |
O1 | 0.066 (5) | 0.085 (6) | 0.042 (4) | −0.016 (4) | 0.001 (3) | −0.019 (4) |
C7 | 0.035 (4) | 0.044 (5) | 0.036 (4) | 0.003 (4) | −0.005 (3) | −0.001 (4) |
C4 | 0.039 (5) | 0.057 (6) | 0.053 (5) | −0.012 (4) | −0.008 (4) | −0.001 (5) |
C10 | 0.052 (6) | 0.060 (6) | 0.047 (5) | −0.001 (5) | 0.020 (4) | −0.005 (5) |
N1 | 0.037 (4) | 0.053 (5) | 0.037 (4) | −0.005 (3) | −0.003 (3) | 0.001 (3) |
C12 | 0.057 (6) | 0.044 (5) | 0.051 (5) | −0.004 (5) | −0.007 (4) | 0.007 (4) |
C5 | 0.033 (4) | 0.035 (4) | 0.034 (4) | −0.003 (3) | −0.002 (3) | 0.000 (3) |
O2 | 0.053 (4) | 0.069 (5) | 0.052 (4) | −0.005 (4) | −0.013 (3) | 0.018 (4) |
C6 | 0.028 (4) | 0.037 (4) | 0.038 (4) | 0.005 (3) | −0.003 (3) | −0.002 (3) |
C9 | 0.036 (5) | 0.058 (6) | 0.060 (6) | 0.018 (4) | −0.002 (4) | 0.003 (5) |
C2 | 0.054 (6) | 0.064 (7) | 0.049 (5) | 0.002 (5) | 0.015 (5) | 0.009 (5) |
C8 | 0.033 (4) | 0.048 (5) | 0.032 (4) | −0.001 (4) | −0.001 (3) | 0.003 (4) |
C1 | 0.047 (5) | 0.067 (6) | 0.036 (4) | 0.006 (5) | −0.005 (4) | 0.000 (4) |
C11 | 0.057 (6) | 0.049 (5) | 0.042 (5) | −0.010 (5) | 0.001 (4) | 0.006 (4) |
C3 | 0.038 (5) | 0.054 (6) | 0.071 (7) | −0.008 (4) | 0.010 (5) | 0.003 (5) |
Geometric parameters (Å, º) top
I1—N2 | 2.291 (8) | C10—C9 | 1.379 (12) |
I1—N1 | 2.245 (7) | C10—C11 | 1.367 (12) |
S1—O1 | 1.417 (8) | C12—H12 | 0.9300 |
S1—N1 | 1.623 (7) | C12—C11 | 1.376 (12) |
S1—C5 | 1.757 (8) | C5—C6 | 1.378 (9) |
S1—O2 | 1.419 (8) | C6—C1 | 1.374 (9) |
N2—C12 | 1.333 (10) | C9—H9 | 0.9300 |
N2—C8 | 1.337 (10) | C9—C8 | 1.376 (11) |
O3—C7 | 1.208 (10) | C2—H2 | 0.9300 |
C7—N1 | 1.378 (11) | C2—C1 | 1.375 (10) |
C7—C6 | 1.490 (11) | C2—C3 | 1.386 (11) |
C4—H4 | 0.9300 | C8—H8 | 0.9300 |
C4—C5 | 1.378 (9) | C1—H1 | 0.9300 |
C4—C3 | 1.380 (10) | C11—H11 | 0.9300 |
C10—H10 | 0.9300 | C3—H3 | 0.9300 |
| | | |
N1—I1—N2 | 175.1 (3) | C4—C5—S1 | 128.8 (6) |
O1—S1—N1 | 111.1 (5) | C4—C5—C6 | 122.6 (7) |
O1—S1—C5 | 111.5 (4) | C6—C5—S1 | 108.6 (5) |
O1—S1—O2 | 116.8 (5) | C5—C6—C7 | 112.4 (7) |
N1—S1—C5 | 94.6 (4) | C1—C6—C7 | 128.5 (7) |
O2—S1—N1 | 110.8 (4) | C1—C6—C5 | 119.1 (7) |
O2—S1—C5 | 109.8 (4) | C10—C9—H9 | 120.7 |
C12—N2—I1 | 119.5 (6) | C8—C9—C10 | 118.7 (8) |
C12—N2—C8 | 119.0 (8) | C8—C9—H9 | 120.7 |
C8—N2—I1 | 120.5 (5) | C1—C2—H2 | 119.8 |
O3—C7—N1 | 124.6 (8) | C1—C2—C3 | 120.4 (8) |
O3—C7—C6 | 125.5 (8) | C3—C2—H2 | 119.8 |
N1—C7—C6 | 109.9 (7) | N2—C8—C9 | 122.0 (8) |
C5—C4—H4 | 121.3 | N2—C8—H8 | 119.0 |
C5—C4—C3 | 117.4 (8) | C9—C8—H8 | 119.0 |
C3—C4—H4 | 121.3 | C6—C1—C2 | 119.7 (8) |
C9—C10—H10 | 120.4 | C6—C1—H1 | 120.2 |
C11—C10—H10 | 120.4 | C2—C1—H1 | 120.2 |
C11—C10—C9 | 119.2 (9) | C10—C11—C12 | 119.2 (9) |
S1—N1—I1 | 117.6 (4) | C10—C11—H11 | 120.4 |
C7—N1—I1 | 127.0 (6) | C12—C11—H11 | 120.4 |
C7—N1—S1 | 114.3 (6) | C4—C3—C2 | 120.8 (8) |
N2—C12—H12 | 119.1 | C4—C3—H3 | 119.6 |
N2—C12—C11 | 121.8 (9) | C2—C3—H3 | 119.6 |
C11—C12—H12 | 119.1 | | |
| | | |
I1—N2—C12—C11 | 167.9 (7) | N1—C7—C6—C1 | −178.1 (9) |
I1—N2—C8—C9 | −169.8 (8) | C12—N2—C8—C9 | −1.3 (14) |
S1—C5—C6—C7 | 3.4 (9) | C5—S1—N1—I1 | −165.1 (5) |
S1—C5—C6—C1 | −179.2 (7) | C5—S1—N1—C7 | 3.5 (7) |
N2—C12—C11—C10 | 1.8 (16) | C5—C4—C3—C2 | −0.7 (16) |
O3—C7—N1—I1 | −13.4 (14) | C5—C6—C1—C2 | 0.0 (15) |
O3—C7—N1—S1 | 179.3 (8) | O2—S1—N1—I1 | 81.6 (6) |
O3—C7—C6—C5 | 177.6 (9) | O2—S1—N1—C7 | −109.7 (7) |
O3—C7—C6—C1 | 0.6 (16) | O2—S1—C5—C4 | −68.2 (10) |
O1—S1—N1—I1 | −49.9 (6) | O2—S1—C5—C6 | 110.1 (7) |
O1—S1—N1—C7 | 118.7 (7) | C6—C7—N1—I1 | 165.3 (6) |
O1—S1—C5—C4 | 62.9 (10) | C6—C7—N1—S1 | −2.0 (10) |
O1—S1—C5—C6 | −118.8 (7) | C9—C10—C11—C12 | −0.9 (16) |
C7—C6—C1—C2 | 176.9 (9) | C8—N2—C12—C11 | −0.7 (14) |
C4—C5—C6—C7 | −178.1 (9) | C1—C2—C3—C4 | 0.0 (17) |
C4—C5—C6—C1 | −0.8 (14) | C11—C10—C9—C8 | −1.0 (16) |
C10—C9—C8—N2 | 2.1 (16) | C3—C4—C5—S1 | 179.3 (8) |
N1—S1—C5—C4 | 177.7 (9) | C3—C4—C5—C6 | 1.1 (15) |
N1—S1—C5—C6 | −4.0 (7) | C3—C2—C1—C6 | 0.4 (17) |
N1—C7—C6—C5 | −1.1 (10) | | |