Impact of the anion and chalcogen on the crystal structure and properties of 4,6-dimethyl-2-pyrimido(thio)­nium halides

By the reaction of urea or thio­urea, acetyl­acetone and hydrogen halide (HF, HBr or HI), we have obtained seven new 4,6-dimethyl-2-pyrimido(thio)­nium salts, which were characterized by single-crystal X-ray diffraction, namely, 4,6-dimethyl-2-oxo-2,3-di­hydro­pyrimidin-1-ium bifluoride, C₆H₉N₂O⁺·HF₂⁻ or (dmpH)F₂H, 4,6-dimethyl-2-oxo-2,3-di­hydro­pyrimidin-1-ium bromide, C₆H₉N₂O⁺·Br⁻ or (dmpH)Br, 4,6-dimethyl-2-oxo-2,3-di­hydro­pyrimidin-1-ium iodide, C₆H₉N₂O⁺·I⁻ or (dmpH)I, 4,6-dimethyl-2-oxo-2,3-di­hydro­pyrimidin-1-ium iodide–urea (1/1), C₆H₉N₂O⁺·I⁻·CH₄N₂O or (dmpH)I·ur, 4,6-dimethyl-2-sul­fan­yl­idene-2,3-di­hydro­pyrimidin-1-ium bifluoride–thio­urea (1/1), C₆H₉N₂S⁺·HF₂⁻·CH₄N₂S or (dmptH)F₂H·tu, 4,6-dimethyl-2-sulfanyl­idene-2,3-di­hydro­pyrimidin-1-ium bromide, C₆H₉N₂S⁺·Br⁻ or (dmptH)Br, and 4,6-dimethyl-2-sulfanyl­idene-2,3-di­hydro­pyrimidin-1-ium iodide, C₆H₉N₂S⁺·I⁻ or (dmptH)I. Three HCl derivatives were described previously in the literature, namely, 4,6-dimethyl-2-oxo-2,3-di­hydro­pyrimidin-1-ium chloride, (dmpH)Cl, 4,6-dimethyl-2-sulfanyl­idene-2,3-di­hydro­pyrimidin-1-ium chloride monohydrate, (dmptH)Cl·H₂O, and 4,6-dimethyl-2-sulfanyl­idene-2,3-di­hydro­pyrimidin-1-ium chloride–thio­urea (1/1), (dmptH)Cl·tu. Structural analysis shows that in 9 out of 10 of these com­pounds, the ions form one-dimensional chains or ribbons stabilized by hydrogen bonds. Only in one com­pound are parallel planes present. In all the structures, there are charge-assisted N⁺—H...X⁻ hydrogen bonds, as well as weaker C_Ar⁺—H...X⁻ and π⁺...X⁻ inter­actions. The structures can be divided into five types according to their hydrogen-bond patterns. All the com­pounds undergo thermal decom­position at relatively high temperatures (150–300 °C) without melting. Four oxopyrimidinium salts containing a π⁺...X⁻...π⁺ sandwich-like structural motif exhibit luminescent properties.

Computing details

For all structures, data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

4,6-Dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium bifluoride (1)

Crystal data

C6H9N2O^+·HF2^−	F(000) = 172
Mr = 164.16	Dx = 1.484 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
a = 7.9253 (16) Å	Cell parameters from 1096 reflections
b = 5.9962 (14) Å	θ = 3.0–29.4°
c = 8.433 (2) Å	µ = 0.14 mm^−1
β = 113.551 (18)°	T = 120 K
V = 367.39 (16) Å^3	Block, colourless
Z = 2	0.25 × 0.04 × 0.04 mm

Data collection

Stoe IPDS 2T diffractometer	1075 independent reflections
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2	1009 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromator	Rint = 0.028
Detector resolution: 6.67 pixels mm^-1	θmax = 29.3°, θmin = 4.3°
rotation method scans	h = −10→10
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)]	k = −8→8
Tmin = 0.949, Tmax = 0.983	l = −11→11
6035 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 0.1674P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1075 reflections	Δρmax = 0.39 e Å^−3
84 parameters	Δρmin = −0.32 e Å^−3
1 restraint

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.71017 (14)	0.250000	0.91063 (13)	0.0205 (2)
N2	0.72246 (15)	0.250000	0.64423 (14)	0.0140 (2)
H2	0.601583	0.250000	0.592192	0.017*
N6	0.99054 (14)	0.250000	0.89619 (14)	0.0137 (2)
H6	1.046662	0.250000	1.009730	0.016*
C1	0.80061 (17)	0.250000	0.82331 (16)	0.0140 (3)
C3	0.81877 (18)	0.250000	0.54510 (16)	0.0142 (3)
C4	1.00892 (18)	0.250000	0.62426 (16)	0.0155 (3)
H4	1.080338	0.250000	0.556716	0.019*
C5	1.09434 (17)	0.250000	0.80387 (17)	0.0142 (3)
C7	0.7107 (2)	0.250000	0.35340 (17)	0.0196 (3)
C8	1.29731 (18)	0.250000	0.90421 (19)	0.0192 (3)
F1	0.36129 (11)	0.250000	0.50873 (11)	0.0214 (2)
H1	0.255 (2)	0.250000	0.3699 (12)	0.064 (9)*
F2	0.13833 (15)	0.250000	0.23660 (11)	0.0316 (3)
H7A	0.790 (3)	0.250000	0.294 (3)	0.030 (5)*
H8A	1.362 (3)	0.250000	0.827 (3)	0.032 (6)*
H8B	1.331 (2)	0.120 (3)	0.9768 (18)	0.031 (4)*
H7B	0.631 (2)	0.121 (3)	0.3222 (19)	0.033 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0167 (5)	0.0302 (6)	0.0178 (5)	0.000	0.0102 (4)	0.000
N2	0.0121 (5)	0.0156 (5)	0.0135 (5)	0.000	0.0044 (4)	0.000
N6	0.0122 (5)	0.0164 (5)	0.0120 (4)	0.000	0.0041 (4)	0.000
C1	0.0134 (6)	0.0147 (6)	0.0144 (6)	0.000	0.0059 (4)	0.000
C3	0.0184 (6)	0.0111 (5)	0.0138 (5)	0.000	0.0071 (5)	0.000
C4	0.0172 (6)	0.0159 (6)	0.0164 (6)	0.000	0.0100 (5)	0.000
C5	0.0136 (5)	0.0122 (5)	0.0175 (6)	0.000	0.0071 (5)	0.000
C7	0.0244 (7)	0.0204 (6)	0.0122 (6)	0.000	0.0055 (5)	0.000
C8	0.0123 (6)	0.0229 (7)	0.0218 (6)	0.000	0.0062 (5)	0.000
F1	0.0143 (4)	0.0300 (5)	0.0168 (4)	0.000	0.0029 (3)	0.000
F2	0.0386 (6)	0.0322 (5)	0.0140 (4)	0.000	0.0001 (4)	0.000

Geometric parameters (Å, º)

O1—C1	1.2156 (16)	C4—C5	1.3904 (18)
N2—H2	0.8800	C5—C8	1.4886 (18)
N2—C1	1.3846 (16)	C7—H7A	0.95 (2)
N2—C3	1.3385 (16)	C7—H7B	0.967 (16)
N6—H6	0.8800	C7—H7B^i	0.967 (16)
N6—C1	1.3800 (16)	C8—H8A	0.98 (2)
N6—C5	1.3396 (16)	C8—H8B	0.962 (16)
C3—C4	1.3831 (18)	C8—H8B^i	0.962 (16)
C3—C7	1.4968 (18)	F1—H1	1.1360 (15)
C4—H4	0.9500	F2—H1	1.1360 (15)
C1—N2—H2	117.9	N6—C5—C4	119.24 (12)
C3—N2—H2	117.9	N6—C5—C8	116.40 (12)
C3—N2—C1	124.28 (11)	C4—C5—C8	124.36 (12)
C1—N6—H6	118.1	C3—C7—H7A	111.2 (13)
C5—N6—H6	118.1	C3—C7—H7B	108.9 (9)
C5—N6—C1	123.71 (11)	C3—C7—H7B^i	108.9 (9)
O1—C1—N2	123.07 (12)	H7A—C7—H7B	110.5 (11)
O1—C1—N6	122.18 (12)	H7A—C7—H7B^i	110.5 (11)
N6—C1—N2	114.75 (11)	H7B—C7—H7B^i	106.7 (18)
N2—C3—C4	118.80 (12)	C5—C8—H8A	111.1 (13)
N2—C3—C7	116.86 (12)	C5—C8—H8B^i	109.1 (9)
C4—C3—C7	124.34 (12)	C5—C8—H8B	109.1 (9)
C3—C4—H4	120.4	H8A—C8—H8B^i	109.5 (11)
C3—C4—C5	119.22 (12)	H8A—C8—H8B	109.5 (11)
C5—C4—H4	120.4	H8B—C8—H8B^i	108.5 (17)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F1	0.88	1.75	2.6240 (15)	175

4,6-Dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium bromide (3)

Crystal data

C6H9N2O^+·Br^−	Dx = 1.723 Mg m^−3
Mr = 205.06	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 16240 reflections
a = 14.4984 (18) Å	θ = 3.8–29.7°
b = 6.722 (2) Å	µ = 5.13 mm^−1
c = 8.113 (7) Å	T = 120 K
V = 790.6 (7) Å^3	Plate, colourless
Z = 4	0.35 × 0.20 × 0.03 mm
F(000) = 408

Data collection

Stoe IPDS 2T diffractometer	1130 independent reflections
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2	971 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromator	Rint = 0.050
Detector resolution: 6.67 pixels mm^-1	θmax = 29.0°, θmin = 3.8°
rotation method scans	h = −19→19
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)]	k = −9→8
Tmin = 0.639, Tmax = 0.905	l = −11→11
10482 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0666P)^2 + 0.2083P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
1130 reflections	Δρmax = 0.74 e Å^−3
75 parameters	Δρmin = −0.59 e Å^−3
12 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.35196 (2)	0.250000	0.50127 (2)	0.02388 (16)
O1	0.58317 (14)	0.250000	0.8135 (2)	0.0371 (5)
N2	0.57782 (16)	0.250000	0.5322 (3)	0.0226 (4)
H2	0.517129	0.250000	0.532890	0.027*
N6	0.71848 (15)	0.250000	0.6681 (3)	0.0248 (4)
H6	0.751254	0.250000	0.759377	0.030*
C3	0.6210 (2)	0.250000	0.3855 (3)	0.0245 (5)
C5	0.7641 (2)	0.250000	0.5243 (3)	0.0242 (5)
C4	0.71538 (19)	0.250000	0.3791 (3)	0.0254 (5)
H4	0.746603	0.250000	0.276126	0.031*
C1	0.62334 (19)	0.250000	0.6826 (3)	0.0266 (5)
C7	0.5611 (2)	0.250000	0.2362 (3)	0.0326 (6)
C8	0.8668 (2)	0.250000	0.5294 (4)	0.0360 (7)
H7A	0.5971 (13)	0.250000	0.1340 (16)	0.049 (12)*
H7B	0.5221 (2)	0.13098 (8)	0.2398 (17)	0.068 (8)*
H8A	0.8902 (18)	0.250000	0.6427 (11)	0.057 (11)*
H8B	0.8890 (9)	0.13099 (8)	0.4719 (10)	0.054 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0223 (2)	0.0298 (2)	0.0195 (2)	0.000	−0.00044 (6)	0.000
O1	0.0251 (9)	0.0693 (15)	0.0169 (9)	0.000	0.0028 (7)	0.000
N2	0.0199 (10)	0.0304 (11)	0.0176 (7)	0.000	0.0006 (8)	0.000
N6	0.0217 (9)	0.0374 (12)	0.0151 (8)	0.000	−0.0005 (7)	0.000
C3	0.0306 (13)	0.0276 (12)	0.0152 (10)	0.000	0.0005 (10)	0.000
C5	0.0230 (13)	0.0293 (12)	0.0204 (9)	0.000	0.0048 (9)	0.000
C4	0.0272 (12)	0.0328 (13)	0.0163 (10)	0.000	0.0024 (9)	0.000
C1	0.0243 (11)	0.0367 (14)	0.0188 (11)	0.000	−0.0009 (10)	0.000
C7	0.0327 (14)	0.0472 (16)	0.0179 (11)	0.000	−0.0034 (10)	0.000
C8	0.0241 (12)	0.057 (2)	0.0273 (11)	0.000	0.0020 (12)	0.000

Geometric parameters (Å, º)

O1—C1	1.211 (3)	C5—C4	1.373 (4)
N2—H2	0.8800	C5—C8	1.490 (4)
N2—C3	1.345 (3)	C4—H4	0.9500
N2—C1	1.387 (3)	C7—H7A	0.9799 (12)
N6—H6	0.8800	C7—H7B^i	0.9800 (8)
N6—C5	1.340 (3)	C7—H7B	0.9800 (8)
N6—C1	1.384 (3)	C8—H8A	0.9802 (12)
C3—C4	1.369 (3)	C8—H8B^i	0.9802 (8)
C3—C7	1.490 (4)	C8—H8B	0.9802 (8)
C3—N2—H2	118.1	O1—C1—N2	122.8 (3)
C3—N2—C1	123.9 (2)	O1—C1—N6	123.6 (3)
C1—N2—H2	118.1	N6—C1—N2	113.5 (2)
C5—N6—H6	117.8	C3—C7—H7A	112.1 (14)
C5—N6—C1	124.4 (2)	C3—C7—H7B	108.2 (7)
C1—N6—H6	117.8	C3—C7—H7B^i	108.2 (7)
N2—C3—C4	119.9 (2)	H7A—C7—H7B	109.44 (13)
N2—C3—C7	116.6 (3)	H7A—C7—H7B^i	109.44 (13)
C4—C3—C7	123.5 (2)	H7B—C7—H7B^i	109.43 (16)
N6—C5—C4	119.5 (3)	C5—C8—H8A	111.8 (16)
N6—C5—C8	118.0 (3)	C5—C8—H8B^i	108.4 (8)
C4—C5—C8	122.5 (2)	C5—C8—H8B	108.4 (8)
C3—C4—C5	118.8 (2)	H8A—C8—H8B^i	109.39 (13)
C3—C4—H4	120.6	H8A—C8—H8B	109.39 (13)
C5—C4—H4	120.6	H8B—C8—H8B^i	109.40 (16)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Br1	0.88	2.41	3.284 (2)	174
N6—H6···Br1^ii	0.88	2.43	3.308 (3)	176

Symmetry code: (ii) x+1/2, y, −z+3/2.

4,6-Dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium iodide (4)

Crystal data

C6H9N2O^+·I^−	F(000) = 240
Mr = 252.05	Dx = 1.899 Mg m^−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.1803 (10) Å	Cell parameters from 1779 reflections
b = 7.2139 (18) Å	θ = 3.4–27.7°
c = 8.6574 (12) Å	µ = 3.57 mm^−1
β = 100.603 (11)°	T = 120 K
V = 440.78 (14) Å^3	Needles, colourless
Z = 2	0.66 × 0.37 × 0.14 mm

Data collection

Stoe IPDS 2T diffractometer	1166 independent reflections
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2	1143 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromator	Rint = 0.066
Detector resolution: 6.67 pixels mm^-1	θmax = 29.0°, θmin = 3.4°
rotation method scans	h = −9→9
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)]	k = −9→9
Tmin = 0.274, Tmax = 0.624	l = −10→11
5622 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.0966P)^2 + 2.7212P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1166 reflections	Δρmax = 1.55 e Å^−3
49 parameters	Δρmin = −1.29 e Å^−3

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.250000	0.36113 (8)	0.750000	0.0398 (3)
C1	0.250000	0.4775 (14)	0.250000	0.0394 (19)
C3	0.2593 (9)	0.7723 (10)	0.3881 (9)	0.0394 (13)
N2	0.2632 (9)	0.5837 (9)	0.3837 (7)	0.0411 (12)
H2	0.275074	0.524688	0.473976	0.049*
C7	0.2664 (18)	0.8639 (11)	0.5416 (12)	0.056 (2)
H7A	0.143381	0.851002	0.574207	0.085*
H7B	0.295644	0.995667	0.532394	0.085*
H7C	0.364872	0.805749	0.620039	0.085*
O1	0.250000	0.3089 (13)	0.250000	0.058 (2)
C4	0.250000	0.8710 (12)	0.250000	0.041 (2)
H4	0.249999	1.002703	0.250000	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0384 (4)	0.0395 (4)	0.0419 (4)	0.000	0.0083 (2)	0.000
C1	0.038 (4)	0.031 (4)	0.048 (5)	0.000	0.006 (4)	0.000
C3	0.034 (3)	0.033 (3)	0.049 (3)	−0.003 (2)	0.003 (2)	0.003 (3)
N2	0.042 (3)	0.042 (3)	0.039 (3)	0.006 (2)	0.005 (2)	0.001 (2)
C7	0.074 (6)	0.045 (5)	0.050 (5)	−0.006 (3)	0.008 (4)	−0.003 (3)
O1	0.089 (7)	0.033 (4)	0.056 (5)	0.000	0.021 (4)	0.000
C4	0.042 (5)	0.025 (4)	0.053 (6)	0.000	0.004 (4)	0.000

Geometric parameters (Å, º)

C1—N2	1.377 (8)	N2—H2	0.8800
C1—N2^i	1.377 (8)	C7—H7A	0.9800
C1—O1	1.216 (14)	C7—H7B	0.9800
C3—N2	1.362 (9)	C7—H7C	0.9800
C3—C7	1.477 (12)	C4—H4	0.9500
C3—C4	1.382 (8)
N2^i—C1—N2	112.4 (9)	C3—C7—H7A	109.5
O1—C1—N2^i	123.8 (4)	C3—C7—H7B	109.5
O1—C1—N2	123.8 (4)	C3—C7—H7C	109.5
N2—C3—C7	118.3 (7)	H7A—C7—H7B	109.5
N2—C3—C4	119.3 (7)	H7A—C7—H7C	109.5
C4—C3—C7	122.4 (7)	H7B—C7—H7C	109.5
C1—N2—H2	117.3	C3^i—C4—C3	118.0 (9)
C3—N2—C1	125.5 (7)	C3—C4—H4	121.0
C3—N2—H2	117.3	C3^i—C4—H4	121.0

Symmetry code: (i) −x+1/2, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···I1	0.88	2.70	3.571 (7)	170

4,6-Dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium iodide–urea (1/1) (5)

Crystal data

C6H9N2O^+·I^−·CH4N2O	F(000) = 608
Mr = 312.11	Dx = 1.829 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.772 (1) Å	Cell parameters from 3188 reflections
b = 11.5579 (10) Å	θ = 3.0–29.4°
c = 14.0700 (16) Å	µ = 2.81 mm^−1
β = 127.378 (7)°	T = 120 K
V = 1133.6 (2) Å^3	Prism, colourless
Z = 4	0.49 × 0.42 × 0.19 mm

Data collection

Stoe IPDS 2T diffractometer	2995 independent reflections
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2	2800 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromator	Rint = 0.050
Detector resolution: 6.67 pixels mm^-1	θmax = 29.0°, θmin = 3.4°
rotation method scans	h = −11→11
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)]	k = −15→15
Tmin = 0.258, Tmax = 0.579	l = −19→19
16324 measured reflections

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)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.6546P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2995 reflections	Δρmax = 0.84 e Å^−3
129 parameters	Δρmin = −1.25 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.83377 (2)	0.74469 (2)	0.35562 (2)	0.02789 (9)
O1U	0.5613 (2)	0.14468 (14)	0.46992 (15)	0.0333 (3)
O1	0.6489 (3)	0.44215 (14)	0.44055 (16)	0.0342 (4)
N2	0.7967 (3)	0.44561 (16)	0.35149 (17)	0.0288 (4)
H2	0.809381	0.521263	0.359539	0.035*
N6	0.6879 (3)	0.27280 (16)	0.37324 (18)	0.0269 (4)
H6	0.627973	0.233371	0.395104	0.032*
N1U	0.4346 (3)	0.29408 (18)	0.5062 (2)	0.0337 (4)
H1UA	0.485102	0.345600	0.486678	0.040*
H1UB	0.365183	0.316836	0.528741	0.040*
C1	0.7072 (3)	0.39069 (18)	0.39252 (19)	0.0274 (4)
C5	0.7551 (3)	0.21480 (19)	0.32306 (19)	0.0279 (4)
C3	0.8663 (3)	0.39169 (18)	0.29974 (19)	0.0281 (4)
C1U	0.4631 (4)	0.1814 (2)	0.5016 (2)	0.0303 (5)
N2U	0.3831 (3)	0.10581 (18)	0.5326 (2)	0.0411 (5)
H2UA	0.399411	0.030962	0.530629	0.049*
H2UB	0.314446	0.131331	0.554735	0.049*
C4	0.8454 (4)	0.2744 (2)	0.2849 (2)	0.0297 (4)
H4	0.892487	0.234216	0.248637	0.036*
C8	0.7286 (4)	0.08672 (19)	0.3136 (2)	0.0347 (5)
H8A	0.844970	0.049635	0.382072	0.052*
H8B	0.703908	0.059710	0.239327	0.052*
H8C	0.619515	0.066691	0.313008	0.052*
C7	0.9637 (4)	0.4651 (2)	0.2641 (2)	0.0354 (5)
H7A	0.877315	0.527494	0.211581	0.053*
H7B	0.997284	0.417626	0.221505	0.053*
H7C	1.080603	0.498420	0.335673	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.03397 (14)	0.01755 (12)	0.03683 (14)	0.00064 (4)	0.02392 (11)	0.00024 (4)
O1U	0.0442 (9)	0.0230 (8)	0.0462 (9)	0.0034 (6)	0.0344 (8)	0.0025 (6)
O1	0.0461 (9)	0.0230 (8)	0.0480 (9)	0.0021 (6)	0.0360 (8)	−0.0009 (6)
N2	0.0394 (9)	0.0168 (8)	0.0387 (10)	0.0001 (7)	0.0282 (8)	−0.0003 (6)
N6	0.0320 (9)	0.0184 (7)	0.0359 (9)	−0.0007 (7)	0.0235 (8)	0.0006 (7)
N1U	0.0496 (12)	0.0185 (9)	0.0459 (11)	0.0028 (8)	0.0358 (10)	0.0011 (8)
C1	0.0304 (9)	0.0197 (9)	0.0350 (10)	0.0006 (7)	0.0215 (8)	0.0004 (7)
C5	0.0337 (10)	0.0193 (9)	0.0329 (10)	0.0011 (8)	0.0214 (9)	−0.0012 (8)
C3	0.0335 (10)	0.0221 (10)	0.0328 (10)	0.0011 (7)	0.0223 (8)	−0.0001 (7)
C1U	0.0362 (11)	0.0247 (11)	0.0363 (11)	0.0012 (8)	0.0253 (9)	0.0013 (8)
N2U	0.0621 (14)	0.0225 (9)	0.0674 (14)	−0.0010 (9)	0.0542 (12)	−0.0022 (9)
C4	0.0385 (12)	0.0209 (9)	0.0370 (11)	0.0014 (9)	0.0267 (10)	−0.0025 (9)
C8	0.0476 (13)	0.0187 (10)	0.0486 (13)	−0.0008 (9)	0.0348 (11)	−0.0020 (8)
C7	0.0512 (13)	0.0225 (10)	0.0482 (12)	−0.0027 (9)	0.0382 (11)	−0.0019 (9)

Geometric parameters (Å, º)

O1U—C1U	1.260 (3)	C3—C4	1.367 (3)
O1—C1	1.221 (3)	C3—C7	1.491 (3)
N2—H2	0.8800	C1U—N2U	1.348 (3)
N2—C1	1.379 (3)	N2U—H2UA	0.8800
N2—C3	1.353 (3)	N2U—H2UB	0.8800
N6—H6	0.8800	C4—H4	0.9500
N6—C1	1.379 (3)	C8—H8A	0.9800
N6—C5	1.342 (3)	C8—H8B	0.9800
N1U—H1UA	0.8800	C8—H8C	0.9800
N1U—H1UB	0.8800	C7—H7A	0.9800
N1U—C1U	1.336 (3)	C7—H7B	0.9800
C5—C4	1.381 (3)	C7—H7C	0.9800
C5—C8	1.492 (3)
C1—N2—H2	117.6	N1U—C1U—N2U	117.8 (2)
C3—N2—H2	117.6	C1U—N2U—H2UA	120.0
C3—N2—C1	124.78 (19)	C1U—N2U—H2UB	120.0
C1—N6—H6	118.1	H2UA—N2U—H2UB	120.0
C5—N6—H6	118.1	C5—C4—H4	120.3
C5—N6—C1	123.8 (2)	C3—C4—C5	119.4 (2)
H1UA—N1U—H1UB	120.0	C3—C4—H4	120.3
C1U—N1U—H1UA	120.0	C5—C8—H8A	109.5
C1U—N1U—H1UB	120.0	C5—C8—H8B	109.5
O1—C1—N2	122.90 (19)	C5—C8—H8C	109.5
O1—C1—N6	123.1 (2)	H8A—C8—H8B	109.5
N2—C1—N6	113.95 (18)	H8A—C8—H8C	109.5
N6—C5—C4	119.6 (2)	H8B—C8—H8C	109.5
N6—C5—C8	116.7 (2)	C3—C7—H7A	109.5
C4—C5—C8	123.7 (2)	C3—C7—H7B	109.5
N2—C3—C4	118.4 (2)	C3—C7—H7C	109.5
N2—C3—C7	117.21 (19)	H7A—C7—H7B	109.5
C4—C3—C7	124.4 (2)	H7A—C7—H7C	109.5
O1U—C1U—N1U	122.3 (2)	H7B—C7—H7C	109.5
O1U—C1U—N2U	119.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···I1	0.88	2.59	3.4692 (19)	173
N6—H6···O1U	0.88	1.80	2.666 (3)	167
N1U—H1UA···O1	0.88	2.21	3.070 (3)	167
N1U—H1UB···I1^i	0.88	3.11	3.883 (2)	148
N2U—H2UA···O1U^ii	0.88	2.06	2.940 (3)	179
N2U—H2UB···I1^i	0.88	2.71	3.565 (2)	166

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1.

4,6-Dimethyl-2-sulfanylidene-2,3-dihydropyrimidin-1-ium bifluoride–thiourea (1/1) (6)

Crystal data

C6H9N2S^+·F2H^−·CH4N2S	F(000) = 268
Mr = 256.34	Dx = 1.457 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
a = 6.3876 (11) Å	Cell parameters from 1229 reflections
b = 8.8268 (13) Å	θ = 3.1–28.7°
c = 10.500 (2) Å	µ = 0.46 mm^−1
β = 99.355 (15)°	T = 120 K
V = 584.15 (17) Å^3	Plate, yellow
Z = 2	0.32 × 0.2 × 0.07 mm

Data collection

Stoe IPDS 2T diffractometer	1532 independent reflections
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2	1375 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromator	Rint = 0.047
Detector resolution: 6.67 pixels mm^-1	θmax = 28.4°, θmin = 3.9°
rotation method scans	h = −7→8
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)]	k = −10→11
Tmin = 0.853, Tmax = 0.967	l = −13→13
3316 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.220	w = 1/[σ^2(Fo^2) + (0.0998P)^2 + 1.0253P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max < 0.001
1532 reflections	Δρmax = 0.55 e Å^−3
80 parameters	Δρmin = −0.49 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1T	0.5456 (2)	0.750000	1.04796 (11)	0.0367 (4)
S1	0.3578 (2)	0.250000	0.63525 (12)	0.0424 (4)
F1	0.2389 (4)	0.6231 (2)	0.5513 (2)	0.0494 (6)
N1T	0.4051 (4)	0.6196 (3)	0.8226 (3)	0.0321 (6)
H1TA	0.355387	0.620829	0.739409	0.038*
H1TB	0.429412	0.532580	0.863319	0.038*
N2	0.2256 (4)	0.3803 (3)	0.4084 (3)	0.0343 (6)
H2	0.252236	0.466934	0.449253	0.041*
C1T	0.4438 (6)	0.750000	0.8874 (4)	0.0281 (8)
C4	0.1035 (6)	0.250000	0.2147 (4)	0.0299 (9)
H4	0.046347	0.250000	0.125352	0.036*
C3	0.1457 (5)	0.3849 (4)	0.2805 (3)	0.0312 (7)
C7	0.1049 (5)	0.5375 (4)	0.2222 (4)	0.0377 (7)
H7A	−0.001766	0.589839	0.263414	0.056*
H7B	0.052706	0.527184	0.129569	0.056*
H7C	0.236850	0.596255	0.235186	0.056*
C1	0.2672 (7)	0.250000	0.4777 (5)	0.0357 (10)
H1	0.261 (15)	0.750000	0.545 (8)	0.08 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1T	0.0486 (7)	0.0226 (6)	0.0379 (6)	0.000	0.0044 (5)	0.000
S1	0.0433 (7)	0.0448 (8)	0.0376 (6)	0.000	0.0023 (5)	0.000
F1	0.0736 (16)	0.0302 (11)	0.0444 (12)	−0.0082 (11)	0.0092 (10)	−0.0031 (9)
N1T	0.0333 (13)	0.0207 (12)	0.0411 (14)	−0.0006 (10)	0.0031 (10)	−0.0007 (10)
N2	0.0333 (13)	0.0276 (14)	0.0421 (14)	−0.0011 (10)	0.0066 (11)	−0.0023 (10)
C1T	0.0260 (18)	0.0223 (19)	0.035 (2)	0.000	0.0037 (15)	0.000
C4	0.0264 (18)	0.024 (2)	0.039 (2)	0.000	0.0062 (16)	0.000
C3	0.0273 (13)	0.0259 (15)	0.0414 (16)	−0.0020 (11)	0.0083 (11)	0.0001 (11)
C7	0.0381 (16)	0.0232 (15)	0.0515 (19)	−0.0008 (12)	0.0068 (13)	0.0017 (13)
C1	0.033 (2)	0.036 (2)	0.038 (2)	0.000	0.0056 (17)	0.000

Geometric parameters (Å, º)

S1T—C1T	1.706 (4)	N2—C1	1.363 (4)
S1—C1	1.662 (5)	C4—H4	0.9500
F1—H1	1.132 (14)	C4—C3^i	1.381 (4)
N1T—H1TA	0.8800	C4—C3	1.381 (4)
N1T—H1TB	0.8800	C3—C7	1.485 (4)
N1T—C1T	1.340 (3)	C7—H7A	0.9800
N2—H2	0.8800	C7—H7B	0.9800
N2—C3	1.357 (4)	C7—H7C	0.9800
H1TA—N1T—H1TB	120.0	N2—C3—C4	118.7 (3)
C1T—N1T—H1TA	120.0	N2—C3—C7	116.6 (3)
C1T—N1T—H1TB	120.0	C4—C3—C7	124.7 (3)
C3—N2—H2	117.9	C3—C7—H7A	109.5
C3—N2—C1	124.2 (3)	C3—C7—H7B	109.5
C1—N2—H2	117.9	C3—C7—H7C	109.5
N1T—C1T—S1T	120.7 (2)	H7A—C7—H7B	109.5
N1T^ii—C1T—S1T	120.7 (2)	H7A—C7—H7C	109.5
N1T^ii—C1T—N1T	118.5 (4)	H7B—C7—H7C	109.5
C3^i—C4—H4	120.4	N2^i—C1—S1	122.5 (2)
C3—C4—H4	120.4	N2—C1—S1	122.5 (2)
C3^i—C4—C3	119.1 (4)	N2—C1—N2^i	115.0 (4)

Symmetry codes: (i) x, −y+1/2, z; (ii) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1T—H1TA···F1	0.88	1.99	2.874 (4)	179
N1T—H1TB···S1T^iii	0.88	2.66	3.528 (3)	170
N2—H2···F1	0.88	1.76	2.610 (4)	163

Symmetry code: (iii) −x+1, −y+1, −z+2.

4,6-Dimethyl-2-sulfanylidene-2,3-dihydropyrimidin-1-ium bromide (9)

Crystal data

C6H9N2S^+·Br^−	F(000) = 440
Mr = 221.12	Dx = 1.725 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.4675 (11) Å	Cell parameters from 2102 reflections
b = 14.9142 (19) Å	θ = 3.8–28.8°
c = 6.8814 (9) Å	µ = 5.02 mm^−1
β = 101.575 (10)°	T = 120 K
V = 851.35 (19) Å^3	Prism, yellow
Z = 4	0.21 × 0.14 × 0.04 mm

Data collection

Stoe IPDS 2T diffractometer	933 independent reflections
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2	871 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromator	Rint = 0.118
Detector resolution: 6.67 pixels mm^-1	θmax = 27.0°, θmin = 3.8°
rotation method scans	h = −10→10
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)]	k = −18→18
Tmin = 0.262, Tmax = 0.740	l = −8→8
5070 measured reflections

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)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.1393P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
933 reflections	Δρmax = 2.21 e Å^−3
49 parameters	Δρmin = −1.62 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.000000	0.19294 (3)	0.250000	0.0325 (3)
S1	0.500000	0.12830 (11)	0.250000	0.0368 (5)
N2	0.3645 (5)	0.2889 (2)	0.2528 (6)	0.0310 (8)
H2	0.273349	0.259950	0.248504	0.037*
C1	0.500000	0.2400 (4)	0.250000	0.0296 (12)
C3	0.3622 (5)	0.3795 (3)	0.2619 (5)	0.0307 (8)
C4	0.500000	0.4264 (4)	0.250000	0.0327 (12)
H4	0.500001	0.490054	0.249997	0.039*
C7	0.2091 (6)	0.4223 (3)	0.2835 (7)	0.0381 (9)
H7A	0.126072	0.410019	0.165295	0.057*
H7B	0.224963	0.487166	0.298873	0.057*
H7C	0.174921	0.397957	0.400812	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0298 (5)	0.0429 (5)	0.0265 (5)	0.000	0.0095 (3)	0.000
S1	0.0363 (8)	0.0359 (9)	0.0419 (9)	0.000	0.0168 (7)	0.000
N2	0.0274 (17)	0.0390 (16)	0.0292 (19)	0.0001 (15)	0.0117 (15)	0.0000 (14)
C1	0.026 (2)	0.033 (3)	0.032 (3)	0.000	0.011 (2)	0.000
C3	0.0262 (17)	0.041 (2)	0.0255 (18)	0.0037 (16)	0.0081 (14)	−0.0010 (15)
C4	0.035 (3)	0.039 (3)	0.025 (3)	0.000	0.008 (2)	0.000
C7	0.031 (2)	0.046 (2)	0.039 (2)	0.0046 (17)	0.0114 (19)	−0.0009 (17)

Geometric parameters (Å, º)

S1—C1	1.665 (6)	C3—C7	1.479 (6)
N2—H2	0.8800	C4—H4	0.9500
N2—C1	1.363 (5)	C7—H7A	0.9800
N2—C3	1.352 (5)	C7—H7B	0.9800
C3—C4	1.377 (5)	C7—H7C	0.9800
C1—N2—H2	118.1	C3^i—C4—C3	119.0 (6)
C3—N2—H2	118.1	C3—C4—H4	120.5
C3—N2—C1	123.8 (4)	C3^i—C4—H4	120.5
N2—C1—S1	122.4 (3)	C3—C7—H7A	109.5
N2^i—C1—S1	122.4 (3)	C3—C7—H7B	109.5
N2—C1—N2^i	115.2 (5)	C3—C7—H7C	109.5
N2—C3—C4	118.9 (4)	H7A—C7—H7B	109.5
N2—C3—C7	117.2 (4)	H7A—C7—H7C	109.5
C4—C3—C7	123.9 (4)	H7B—C7—H7C	109.5

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Br1	0.88	2.52	3.399 (4)	174

4,6-Dimethyl-2-sulfanylidene-2,3-dihydropyrimidin-1-ium iodide (10)

Crystal data

C6H9N2S^+·I^−	Dx = 1.913 Mg m^−3
Mr = 268.11	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Cmcm	Cell parameters from 1294 reflections
a = 8.7198 (14) Å	θ = 3.9–26.7°
b = 15.095 (3) Å	µ = 3.60 mm^−1
c = 7.0716 (11) Å	T = 120 K
V = 930.8 (3) Å^3	Plate, yellow
Z = 4	0.17 × 0.12 × 0.05 mm
F(000) = 512

Data collection

Stoe IPDS 2T diffractometer	708 independent reflections
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2	661 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromator	Rint = 0.058
Detector resolution: 6.67 pixels mm^-1	θmax = 28.9°, θmin = 4.0°
rotation method scans	h = −11→11
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), analogous to Coppens (1970)]	k = −20→20
Tmin = 0.520, Tmax = 0.837	l = −9→9
7434 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.060	w = 1/[σ^2(Fo^2) + (0.0431P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
708 reflections	Δρmax = 1.10 e Å^−3
42 parameters	Δρmin = −0.88 e Å^−3
6 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.000000	0.18528 (2)	0.750000	0.02004 (12)
S1	0.500000	0.12787 (8)	0.750000	0.0258 (3)
N2	0.3682 (3)	0.28725 (19)	0.750000	0.0195 (6)
H2	0.280127	0.258795	0.750000	0.023*
C1	0.500000	0.2378 (3)	0.750000	0.0198 (9)
C4	0.500000	0.4226 (3)	0.750000	0.0201 (9)
H4	0.499999	0.485535	0.750000	0.024*
C3	0.3643 (4)	0.3766 (2)	0.750000	0.0201 (6)
C7	0.2109 (5)	0.4189 (2)	0.750000	0.0298 (8)
H7A	0.220 (4)	0.4836 (3)	0.750000	0.062 (18)*
H7B	0.1549 (12)	0.3999 (11)	0.63687 (7)	0.049 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01939 (17)	0.01578 (17)	0.02494 (19)	0.000	0.000	0.000
S1	0.0231 (6)	0.0113 (5)	0.0429 (8)	0.000	0.000	0.000
N2	0.0177 (12)	0.0140 (12)	0.0267 (15)	−0.0014 (10)	0.000	0.000
C1	0.021 (2)	0.015 (2)	0.024 (2)	0.000	0.000	0.000
C4	0.020 (2)	0.014 (2)	0.026 (3)	0.000	0.000	0.000
C3	0.0229 (15)	0.0128 (14)	0.0246 (17)	0.0039 (12)	0.000	0.000
C7	0.0262 (17)	0.0175 (15)	0.046 (3)	0.0071 (13)	0.000	0.000

Geometric parameters (Å, º)

S1—C1	1.659 (5)	C4—C3^i	1.372 (4)
N2—H2	0.8800	C3—C7	1.482 (5)
N2—C1	1.371 (4)	C7—H7A	0.9800 (11)
N2—C3	1.350 (4)	C7—H7B	0.9800 (7)
C4—H4	0.9500	C7—H7B^ii	0.9800 (7)
C4—C3	1.372 (4)
C1—N2—H2	117.8	N2—C3—C4	118.9 (3)
C3—N2—H2	117.8	N2—C3—C7	117.0 (3)
C3—N2—C1	124.5 (3)	C4—C3—C7	124.1 (3)
N2^i—C1—S1	123.0 (2)	C3—C7—H7A	111 (2)
N2—C1—S1	123.0 (2)	C3—C7—H7B	108.9 (10)
N2^i—C1—N2	113.9 (4)	C3—C7—H7B^ii	108.9 (10)
C3—C4—H4	120.4	H7A—C7—H7B	109.43 (13)
C3^i—C4—H4	120.4	H7A—C7—H7B^ii	109.43 (13)
C3—C4—C3^i	119.2 (4)	H7B—C7—H7B^ii	109.43 (16)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···I1	0.88	2.68	3.561 (3)	175