N-Iodosaccharin–pyridine co-crystal system under pressure: experimental evidence of reversible twinning

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 B2₁/e). The unconventional setting of the space group is adopted (the conventional setting is P2₁/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_sac...I...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 B2₁/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.

Computing details

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)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.15 × 0.12 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.019	H-atom parameters constrained
wR(F^2) = 0.050	w = 1/[σ^2(Fo^2) + (0.021P)^2 + 3.1655P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.15 × 0.12 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.015	H-atom parameters constrained
wR(F^2) = 0.038	w = 1/[σ^2(Fo^2) + (0.0114P)^2 + 7.3244P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0411P)^2 + 9.578P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_0.00_d_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 19.6592P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_0.05_d_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0332P)^2 + 36.6993P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_0.20_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0489P)^2 + 9.4112P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_0.4_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0536P)^2 + 2.7067P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_0.5_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0402P)^2 + 16.5567P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_0.5_d_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0416P)^2 + 22.312P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_0.8_d_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0423P)^2 + 29.2986P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_0.9_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0368P)^2 + 25.1886P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_1.3_d_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0253P)^2 + 80.1818P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_1.5_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0269P)^2 + 58.096P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_1.9_d_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.014P)^2 + 86.6837P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_2.0_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0196P)^2 + 88.6924P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_2.4_d_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + 65.621P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_3.3_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.020	H-atom parameters constrained
wR(F^2) = 0.038	w = 1/[σ^2(Fo^2) + (0.0102P)^2 + 7.7918P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(dac_4.5_GPa)

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.049	w = 1/[σ^2(Fo^2) + 18.6464P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

Crystal data

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) Å^3	Plate, orange
Z = 8	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.155	w = 1/[σ^2(Fo^2) + (0.0572P)^2 + 59.271P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)