Crystal structure of N,N′-bis­[3-(methyl­sulfan­yl)prop­yl]-1,8:4,5-naphthalene­tetra­carb­oxy­lic di­imide

The title compound was synthesized from naphthalene di­imide and methyl­thio­propi­amine. The asymmetric unit consists of half of the total mol­ecule as the mol­ecule lies on an inversion center. Intra­molecular C—H...O and C—H...S hydrogen bonds cause the mol­ecule to have an anti conformation. In the crystal, C—H...O and C—H...S hydrogen bonds and π–π inter­actions lead to the formation of a two-dimensional network structure parallel to (110). Hirshfeld surface analysis confirmed the inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.101
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.346 Check

Alert level G
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        56% Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 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
   3 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

N,N'-Bis[3-(methylsulfanyl)propyl]-1,8:4,5-naphthalenetetracarboxylic diimide

Crystal data

C22H22N2O4S2	F(000) = 464
Mr = 442.53	Dx = 1.485 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0500 (2) Å	Cell parameters from 1676 reflections
b = 4.9407 (1) Å	θ = 3.1–26.1°
c = 24.9626 (7) Å	µ = 0.30 mm^−1
β = 94.333 (2)°	T = 173 K
V = 989.99 (4) Å^3	Rod, yellow
Z = 2	0.23 × 0.05 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer	1360 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.046
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θmax = 25.0°, θmin = 1.6°
Tmin = 0.676, Tmax = 0.746	h = −9→9
5641 measured reflections	k = −5→5
1732 independent reflections	l = −29→25

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0403P)^2 + 0.3426P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1732 reflections	Δρmax = 0.25 e Å^−3
137 parameters	Δρmin = −0.26 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
S1	0.25895 (9)	0.32924 (13)	0.17605 (3)	0.0356 (2)
O1	0.5336 (2)	0.2804 (3)	0.04996 (7)	0.0310 (4)
O2	0.8407 (2)	0.9669 (3)	0.12693 (6)	0.0326 (5)
N1	0.6852 (2)	0.6297 (4)	0.08708 (8)	0.0243 (5)
C1	0.0764 (4)	0.4611 (6)	0.20299 (12)	0.0458 (8)
H1A	0.0888	0.4506	0.2423	0.069*
H1B	−0.0207	0.3548	0.1895	0.069*
H1C	0.0609	0.6503	0.1919	0.069*
C2	0.4130 (3)	0.5621 (5)	0.20506 (10)	0.0273 (6)
H2A	0.3685	0.7488	0.2024	0.033*
H2B	0.4374	0.5191	0.2436	0.033*
C3	0.5728 (3)	0.5448 (5)	0.17623 (9)	0.0276 (6)
H3A	0.6650	0.6315	0.1985	0.033*
H3B	0.6023	0.3526	0.1710	0.033*
C4	0.5500 (3)	0.6857 (5)	0.12200 (10)	0.0274 (6)
H4A	0.4431	0.6269	0.1035	0.033*
H4B	0.5434	0.8834	0.1279	0.033*
C5	0.6592 (3)	0.4151 (4)	0.05056 (9)	0.0243 (6)
C6	0.7912 (3)	0.3668 (4)	0.01356 (9)	0.0214 (5)
C7	0.9374 (3)	0.5241 (4)	0.01778 (8)	0.0200 (5)
C8	0.9613 (3)	0.7304 (4)	0.05690 (9)	0.0228 (5)
C9	0.8287 (3)	0.7878 (4)	0.09317 (9)	0.0249 (6)
C10	0.7698 (3)	0.1661 (4)	−0.02484 (9)	0.0234 (5)
H10	0.6712	0.0598	−0.0273	0.028*
C11	1.1054 (3)	0.8802 (4)	0.06017 (9)	0.0242 (6)
H11	1.1210	1.0173	0.0868	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0366 (5)	0.0304 (4)	0.0400 (4)	−0.0049 (3)	0.0038 (3)	−0.0064 (3)
O1	0.0268 (11)	0.0293 (9)	0.0371 (10)	−0.0088 (8)	0.0036 (8)	−0.0010 (8)
O2	0.0372 (11)	0.0284 (9)	0.0322 (10)	−0.0041 (8)	0.0025 (8)	−0.0113 (8)
N1	0.0252 (12)	0.0200 (10)	0.0273 (11)	−0.0021 (9)	0.0009 (9)	−0.0004 (8)
C1	0.0360 (19)	0.0483 (17)	0.0541 (19)	−0.0024 (14)	0.0104 (14)	0.0018 (15)
C2	0.0320 (16)	0.0220 (12)	0.0276 (13)	−0.0002 (11)	−0.0003 (11)	−0.0003 (10)
C3	0.0292 (15)	0.0272 (13)	0.0260 (13)	0.0017 (11)	−0.0011 (11)	−0.0019 (10)
C4	0.0254 (15)	0.0255 (13)	0.0314 (14)	0.0034 (11)	0.0038 (11)	0.0005 (11)
C5	0.0275 (15)	0.0199 (12)	0.0247 (13)	−0.0006 (11)	−0.0034 (10)	0.0039 (10)
C6	0.0237 (14)	0.0150 (11)	0.0248 (13)	0.0001 (10)	−0.0031 (10)	0.0028 (9)
C7	0.0226 (14)	0.0152 (11)	0.0214 (12)	−0.0006 (10)	−0.0037 (9)	0.0028 (9)
C8	0.0253 (14)	0.0178 (11)	0.0246 (13)	−0.0015 (10)	−0.0026 (10)	0.0028 (9)
C9	0.0284 (15)	0.0211 (12)	0.0246 (13)	0.0008 (10)	−0.0021 (10)	0.0034 (10)
C10	0.0220 (14)	0.0198 (12)	0.0273 (13)	−0.0028 (10)	−0.0065 (10)	0.0044 (10)
C11	0.0302 (15)	0.0177 (11)	0.0236 (13)	−0.0019 (10)	−0.0045 (10)	−0.0018 (9)

Geometric parameters (Å, º)

S1—C1	1.785 (3)	C3—H3B	0.9900
S1—C2	1.803 (2)	C4—H4A	0.9900
O1—C5	1.210 (3)	C4—H4B	0.9900
O2—C9	1.221 (3)	C5—C6	1.479 (3)
N1—C9	1.394 (3)	C6—C10	1.381 (3)
N1—C5	1.404 (3)	C6—C7	1.408 (3)
N1—C4	1.471 (3)	C7—C7^i	1.413 (4)
C1—H1A	0.9800	C7—C8	1.415 (3)
C1—H1B	0.9800	C8—C11	1.373 (3)
C1—H1C	0.9800	C8—C9	1.478 (3)
C2—C3	1.523 (3)	C10—C11^i	1.404 (3)
C2—H2A	0.9900	C10—H10	0.9500
C2—H2B	0.9900	C11—C10^i	1.404 (3)
C3—C4	1.521 (3)	C11—H11	0.9500
C3—H3A	0.9900
C1—S1—C2	100.17 (12)	N1—C4—H4B	108.9
C9—N1—C5	125.2 (2)	C3—C4—H4B	108.9
C9—N1—C4	118.31 (19)	H4A—C4—H4B	107.7
C5—N1—C4	116.52 (19)	O1—C5—N1	120.4 (2)
S1—C1—H1A	109.5	O1—C5—C6	122.9 (2)
S1—C1—H1B	109.5	N1—C5—C6	116.7 (2)
H1A—C1—H1B	109.5	C10—C6—C7	120.5 (2)
S1—C1—H1C	109.5	C10—C6—C5	119.5 (2)
H1A—C1—H1C	109.5	C7—C6—C5	120.0 (2)
H1B—C1—H1C	109.5	C6—C7—C7^i	119.5 (2)
C3—C2—S1	110.75 (16)	C6—C7—C8	121.3 (2)
C3—C2—H2A	109.5	C7^i—C7—C8	119.3 (3)
S1—C2—H2A	109.5	C11—C8—C7	120.0 (2)
C3—C2—H2B	109.5	C11—C8—C9	120.4 (2)
S1—C2—H2B	109.5	C7—C8—C9	119.6 (2)
H2A—C2—H2B	108.1	O2—C9—N1	120.2 (2)
C4—C3—C2	110.2 (2)	O2—C9—C8	122.6 (2)
C4—C3—H3A	109.6	N1—C9—C8	117.2 (2)
C2—C3—H3A	109.6	C6—C10—C11^i	119.7 (2)
C4—C3—H3B	109.6	C6—C10—H10	120.1
C2—C3—H3B	109.6	C11^i—C10—H10	120.1
H3A—C3—H3B	108.1	C8—C11—C10^i	121.1 (2)
N1—C4—C3	113.37 (19)	C8—C11—H11	119.5
N1—C4—H4A	108.9	C10^i—C11—H11	119.5
C3—C4—H4A	108.9
C1—S1—C2—C3	−163.99 (17)	C6—C7—C8—C11	179.8 (2)
S1—C2—C3—C4	75.4 (2)	C7^i—C7—C8—C11	−0.3 (4)
C9—N1—C4—C3	−84.9 (2)	C6—C7—C8—C9	−1.7 (3)
C5—N1—C4—C3	94.0 (2)	C7^i—C7—C8—C9	178.1 (2)
C2—C3—C4—N1	−167.95 (19)	C5—N1—C9—O2	−178.5 (2)
C9—N1—C5—O1	176.4 (2)	C4—N1—C9—O2	0.3 (3)
C4—N1—C5—O1	−2.5 (3)	C5—N1—C9—C8	2.2 (3)
C9—N1—C5—C6	−4.1 (3)	C4—N1—C9—C8	−178.94 (19)
C4—N1—C5—C6	177.07 (18)	C11—C8—C9—O2	0.0 (3)
O1—C5—C6—C10	2.3 (3)	C7—C8—C9—O2	−178.4 (2)
N1—C5—C6—C10	−177.28 (19)	C11—C8—C9—N1	179.24 (19)
O1—C5—C6—C7	−177.5 (2)	C7—C8—C9—N1	0.8 (3)
N1—C5—C6—C7	3.0 (3)	C7—C6—C10—C11^i	−0.4 (3)
C10—C6—C7—C7^i	0.2 (4)	C5—C6—C10—C11^i	179.8 (2)
C5—C6—C7—C7^i	179.9 (2)	C7—C8—C11—C10^i	0.5 (3)
C10—C6—C7—C8	−179.9 (2)	C9—C8—C11—C10^i	−177.9 (2)
C5—C6—C7—C8	−0.2 (3)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···S1	0.99	2.84	3.300 (2)	109
C4—H4A···O1	0.99	2.32	2.688 (3)	101
C10—H10···O1^ii	0.95	2.39	3.316 (3)	164
C11—H11···S1^iii	0.95	2.86	3.779 (2)	162

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