Crystal structure and Hirshfeld surface analysis of a new di­thio­glycoluril: 1,4-bis­(4-meth­oxy­phen­yl)-3a-methyl­tetra­hydro­imidazo[4,5-d]imidazole-2,5(1H,3H)-di­thione

In the title di­thio­glycoluril derivative, there is a difference in the torsion angles between the thio­imidazole moiety and the meth­oxy­phenyl groups on either side of the mol­ecule [C—N—C_ar—C_ar = 116.9 (2) and −86.1 (3)°]. The N—C—N bond angle on one side of the di­thio­glycoluril moiety is slightly smaller than the one on the opposite side [110.9 (2)° cf. 112.0 (2)°], probably as a result of the steric effect of the methyl group.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.156
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.990 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT793_ALERT_4_G Model has Chirality at C2          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         46 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1,4-Bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione

Crystal data

C19H20N4O2S2	F(000) = 840
Mr = 400.51	Dx = 1.398 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.1955 (3) Å	Cell parameters from 11825 reflections
b = 10.0157 (2) Å	θ = 3.4–73.8°
c = 14.5476 (3) Å	µ = 2.73 mm^−1
β = 98.329 (2)°	T = 100 K
V = 1902.36 (7) Å^3	Plate, clear colourless
Z = 4	0.12 × 0.05 × 0.01 mm

Data collection

Rigaku Oxford Diffraction XtaLAB Synergy, Dualflex, Pilatus 200K diffractometer	3824 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3267 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.053
ω scans	θmax = 74.2°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	h = −16→15
Tmin = 0.735, Tmax = 1.000	k = −12→12
25390 measured reflections	l = −18→15

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.156	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.22	(Δ/σ)max = 0.001
3824 reflections	Δρmax = 0.63 e Å^−3
247 parameters	Δρmin = −0.53 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
S2	0.42015 (4)	0.63758 (5)	0.56357 (4)	0.02883 (19)
S1	0.69303 (4)	0.64039 (6)	0.20550 (4)	0.03272 (19)
O2	0.05235 (12)	0.52239 (19)	0.24656 (13)	0.0411 (4)
O1	1.06251 (13)	0.6869 (2)	0.55605 (14)	0.0501 (5)
N3	0.42969 (13)	0.73812 (19)	0.39262 (13)	0.0282 (4)
N1	0.66847 (13)	0.76111 (19)	0.36715 (13)	0.0282 (4)
N4	0.56744 (13)	0.7746 (2)	0.49428 (13)	0.0302 (4)
H4	0.607926	0.773181	0.546222	0.036*
N2	0.52813 (13)	0.7489 (2)	0.26451 (13)	0.0321 (4)
H2	0.488712	0.728354	0.214118	0.039*
C6	0.33311 (15)	0.6860 (2)	0.35217 (14)	0.0278 (4)
C5	0.47370 (15)	0.7169 (2)	0.48150 (15)	0.0269 (4)
C13	0.77144 (15)	0.7412 (2)	0.41232 (15)	0.0285 (5)
C2	0.49454 (16)	0.8198 (2)	0.34048 (15)	0.0288 (5)
H2A	0.462130	0.905134	0.320659	0.035*
C9	0.14274 (16)	0.5846 (2)	0.27955 (16)	0.0326 (5)
C1	0.62924 (16)	0.7179 (2)	0.28148 (15)	0.0290 (4)
C3	0.59244 (16)	0.8391 (2)	0.41109 (16)	0.0294 (5)
C11	0.31898 (16)	0.5490 (2)	0.34585 (16)	0.0326 (5)
H11	0.373181	0.491552	0.365398	0.039*
C10	0.22374 (17)	0.4982 (2)	0.31029 (17)	0.0355 (5)
H10	0.213660	0.406289	0.306848	0.043*
C8	0.15769 (17)	0.7205 (3)	0.28276 (17)	0.0346 (5)
H8	0.104211	0.778010	0.261024	0.041*
C7	0.25360 (17)	0.7716 (3)	0.31882 (17)	0.0345 (5)
H7	0.264271	0.863400	0.320503	0.041*
C14	0.84562 (18)	0.8354 (3)	0.40334 (17)	0.0370 (5)
H14	0.829035	0.910173	0.366309	0.044*
C16	0.96858 (17)	0.7111 (3)	0.50581 (18)	0.0383 (6)
C15	0.94482 (18)	0.8197 (3)	0.44908 (17)	0.0393 (6)
H15	0.994904	0.882321	0.441325	0.047*
C18	0.79544 (19)	0.6308 (2)	0.4673 (2)	0.0383 (6)
H18	0.745801	0.566657	0.473044	0.046*
C4	0.62578 (19)	0.9834 (3)	0.42760 (19)	0.0391 (6)
H4A	0.685302	0.986734	0.474091	0.059*
H4B	0.571319	1.033392	0.448355	0.059*
H4C	0.641782	1.021121	0.370769	0.059*
C12	−0.03793 (18)	0.6032 (3)	0.2306 (2)	0.0427 (6)
H12A	−0.033051	0.663519	0.180189	0.064*
H12B	−0.044452	0.653243	0.285733	0.064*
H12C	−0.096868	0.546930	0.215268	0.064*
C17	0.8940 (2)	0.6156 (3)	0.5143 (2)	0.0432 (6)
H17	0.910343	0.541071	0.551726	0.052*
C19	1.14391 (19)	0.7756 (4)	0.5431 (2)	0.0588 (9)
H19A	1.151078	0.778830	0.478399	0.088*
H19B	1.206604	0.744313	0.578239	0.088*
H19C	1.128777	0.863354	0.563931	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S2	0.0231 (3)	0.0352 (3)	0.0281 (3)	−0.00311 (18)	0.0035 (2)	0.00066 (19)
S1	0.0274 (3)	0.0385 (3)	0.0323 (3)	0.0050 (2)	0.0046 (2)	−0.0049 (2)
O2	0.0238 (8)	0.0425 (10)	0.0540 (11)	0.0022 (7)	−0.0052 (7)	−0.0128 (8)
O1	0.0242 (8)	0.0612 (13)	0.0617 (12)	0.0036 (8)	−0.0043 (8)	−0.0093 (10)
N3	0.0207 (8)	0.0359 (10)	0.0283 (9)	−0.0014 (7)	0.0043 (7)	0.0021 (7)
N1	0.0203 (8)	0.0334 (10)	0.0313 (9)	0.0005 (7)	0.0049 (7)	−0.0038 (7)
N4	0.0218 (8)	0.0410 (11)	0.0281 (9)	−0.0041 (7)	0.0050 (7)	−0.0020 (8)
N2	0.0223 (8)	0.0439 (11)	0.0298 (10)	0.0034 (8)	0.0028 (7)	−0.0014 (8)
C6	0.0218 (10)	0.0368 (12)	0.0245 (10)	0.0012 (8)	0.0031 (8)	−0.0011 (9)
C5	0.0219 (9)	0.0290 (10)	0.0299 (10)	0.0014 (8)	0.0037 (8)	−0.0034 (8)
C13	0.0230 (10)	0.0336 (11)	0.0294 (11)	−0.0037 (8)	0.0055 (8)	−0.0073 (9)
C2	0.0253 (10)	0.0321 (11)	0.0298 (11)	0.0019 (8)	0.0069 (8)	0.0021 (9)
C9	0.0251 (11)	0.0397 (12)	0.0319 (11)	0.0037 (9)	0.0006 (8)	−0.0074 (9)
C1	0.0279 (10)	0.0298 (10)	0.0295 (11)	−0.0001 (8)	0.0055 (8)	0.0012 (8)
C3	0.0261 (10)	0.0322 (11)	0.0318 (11)	−0.0005 (8)	0.0101 (8)	−0.0035 (9)
C11	0.0248 (10)	0.0362 (12)	0.0349 (12)	0.0074 (9)	−0.0020 (8)	−0.0034 (9)
C10	0.0291 (11)	0.0322 (12)	0.0430 (13)	0.0016 (9)	−0.0027 (9)	−0.0046 (10)
C8	0.0251 (10)	0.0397 (13)	0.0378 (12)	0.0081 (9)	0.0012 (9)	0.0006 (10)
C7	0.0286 (11)	0.0341 (12)	0.0397 (12)	0.0022 (9)	0.0010 (9)	0.0007 (10)
C14	0.0289 (11)	0.0451 (13)	0.0368 (12)	−0.0083 (10)	0.0041 (9)	0.0045 (10)
C16	0.0259 (11)	0.0487 (14)	0.0395 (13)	0.0019 (10)	0.0018 (9)	−0.0091 (11)
C15	0.0282 (11)	0.0519 (15)	0.0387 (13)	−0.0098 (10)	0.0074 (9)	−0.0026 (11)
C18	0.0281 (11)	0.0340 (12)	0.0517 (15)	−0.0039 (9)	0.0020 (10)	−0.0011 (10)
C4	0.0382 (12)	0.0334 (12)	0.0478 (14)	−0.0015 (10)	0.0128 (10)	−0.0048 (10)
C12	0.0240 (11)	0.0507 (15)	0.0518 (15)	0.0035 (10)	0.0002 (10)	−0.0070 (12)
C17	0.0343 (13)	0.0375 (13)	0.0557 (16)	0.0026 (10)	−0.0005 (11)	0.0040 (11)
C19	0.0237 (12)	0.103 (3)	0.0501 (16)	−0.0083 (14)	0.0054 (11)	−0.0106 (16)

Geometric parameters (Å, º)

S2—C5	1.674 (2)	C9—C8	1.375 (4)
S1—C1	1.674 (2)	C3—C4	1.520 (3)
O2—C9	1.370 (3)	C11—H11	0.9300
O2—C12	1.431 (3)	C11—C10	1.385 (3)
O1—C16	1.366 (3)	C10—H10	0.9300
O1—C19	1.427 (4)	C8—H8	0.9300
N3—C6	1.423 (3)	C8—C7	1.395 (3)
N3—C5	1.355 (3)	C7—H7	0.9300
N3—C2	1.472 (3)	C14—H14	0.9300
N1—C13	1.435 (3)	C14—C15	1.389 (3)
N1—C1	1.350 (3)	C16—C15	1.374 (4)
N1—C3	1.487 (3)	C16—C17	1.391 (4)
N4—H4	0.8600	C15—H15	0.9300
N4—C5	1.353 (3)	C18—H18	0.9300
N4—C3	1.451 (3)	C18—C17	1.388 (4)
N2—H2	0.8600	C4—H4A	0.9600
N2—C2	1.437 (3)	C4—H4B	0.9600
N2—C1	1.357 (3)	C4—H4C	0.9600
C6—C11	1.386 (3)	C12—H12A	0.9600
C6—C7	1.387 (3)	C12—H12B	0.9600
C13—C14	1.379 (3)	C12—H12C	0.9600
C13—C18	1.374 (3)	C17—H17	0.9300
C2—H2A	0.9800	C19—H19A	0.9600
C2—C3	1.542 (3)	C19—H19B	0.9600
C9—C10	1.398 (3)	C19—H19C	0.9600
C9—O2—C12	117.5 (2)	C10—C11—H11	120.2
C16—O1—C19	117.4 (2)	C9—C10—H10	119.9
C6—N3—C2	122.93 (17)	C11—C10—C9	120.1 (2)
C5—N3—C6	124.84 (18)	C11—C10—H10	119.9
C5—N3—C2	112.21 (17)	C9—C8—H8	120.2
C13—N1—C3	121.96 (18)	C9—C8—C7	119.6 (2)
C1—N1—C13	126.11 (18)	C7—C8—H8	120.2
C1—N1—C3	111.89 (17)	C6—C7—C8	120.3 (2)
C5—N4—H4	123.6	C6—C7—H7	119.9
C5—N4—C3	112.89 (18)	C8—C7—H7	119.9
C3—N4—H4	123.6	C13—C14—H14	119.7
C2—N2—H2	123.9	C13—C14—C15	120.6 (2)
C1—N2—H2	123.9	C15—C14—H14	119.7
C1—N2—C2	112.18 (18)	O1—C16—C15	124.9 (2)
C11—C6—N3	119.63 (19)	O1—C16—C17	115.4 (2)
C11—C6—C7	120.1 (2)	C15—C16—C17	119.7 (2)
C7—C6—N3	120.3 (2)	C14—C15—H15	120.2
N3—C5—S2	126.03 (16)	C16—C15—C14	119.7 (2)
N4—C5—S2	125.21 (16)	C16—C15—H15	120.2
N4—C5—N3	108.73 (19)	C13—C18—H18	120.1
C14—C13—N1	119.9 (2)	C13—C18—C17	119.7 (2)
C18—C13—N1	120.11 (19)	C17—C18—H18	120.1
C18—C13—C14	119.9 (2)	C3—C4—H4A	109.5
N3—C2—H2A	112.0	C3—C4—H4B	109.5
N3—C2—C3	102.70 (17)	C3—C4—H4C	109.5
N2—C2—N3	112.86 (19)	H4A—C4—H4B	109.5
N2—C2—H2A	112.0	H4A—C4—H4C	109.5
N2—C2—C3	104.61 (17)	H4B—C4—H4C	109.5
C3—C2—H2A	112.0	O2—C12—H12A	109.5
O2—C9—C10	114.6 (2)	O2—C12—H12B	109.5
O2—C9—C8	125.1 (2)	O2—C12—H12C	109.5
C8—C9—C10	120.2 (2)	H12A—C12—H12B	109.5
N1—C1—S1	126.59 (16)	H12A—C12—H12C	109.5
N1—C1—N2	109.29 (19)	H12B—C12—H12C	109.5
N2—C1—S1	124.11 (17)	C16—C17—H17	119.8
N1—C3—C2	101.56 (17)	C18—C17—C16	120.3 (2)
N1—C3—C4	111.68 (18)	C18—C17—H17	119.8
N4—C3—N1	111.96 (19)	O1—C19—H19A	109.5
N4—C3—C2	103.31 (17)	O1—C19—H19B	109.5
N4—C3—C4	112.76 (19)	O1—C19—H19C	109.5
C4—C3—C2	114.8 (2)	H19A—C19—H19B	109.5
C6—C11—H11	120.2	H19A—C19—H19C	109.5
C10—C11—C6	119.7 (2)	H19B—C19—H19C	109.5

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S2^i	0.86	2.62	3.265 (2)	133
N4—H4···S1^ii	0.86	2.57	3.382 (2)	157
C7—H7···S1^iii	0.93	2.87	3.786 (3)	170
C12—H12B···Cg^iv	0.96	2.99	3.893 (3)	157

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