(E)-1-(5-Methyl­thio­phen-2-yl)-N-(4-nitro­phen­yl)methanimine

The title compound, C₁₂H₁₀N₂O₂S, was synthesized via the acid-catalyzed condensation of 4-nitro­aniline and 5-methyl-2-thio­phene­carboxaldehyde in a methanol–water solution. The dihedral angle between the benzene and thio­phene rings is 54.62 (3)°. No directional inter­actions could be identified in the extended structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.123
• Data-to-parameter ratio = 27.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.532 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).         10 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          3 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        290 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: OLEX2 (Bourhis et al., 2015).

(E)-1-(5-Methylthiophen-2-yl)-N-(4-nitrophenyl)methanimine

Crystal data

C12H10N2O2S	Dx = 1.416 Mg m^−3
Mr = 246.28	Melting point: 429 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.5979 (7) Å	Cell parameters from 8567 reflections
b = 7.3148 (3) Å	θ = 4.5–32.7°
c = 12.5931 (6) Å	µ = 0.27 mm^−1
β = 112.763 (5)°	T = 293 K
V = 1155.04 (9) Å^3	Plate, yellow
Z = 4	0.34 × 0.32 × 0.19 mm
F(000) = 512

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4318 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3467 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 16.1790 pixels mm^-1	θmax = 33.7°, θmin = 4.3°
ω scans	h = −20→21
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→11
Tmin = 0.796, Tmax = 1.000	l = −19→19
28914 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.056P)^2 + 0.2252P] where P = (Fo^2 + 2Fc^2)/3
4318 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.33 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

H atoms were included in calculated positions with C—H distances of 0.93 Å and 0.96 Å based upon type of carbon atom and were included in the refinement in riding motion approximation with U_iso = 1.2U_eq(carrier) or 1.5U_eq(methyl carrier).

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

	x	y	z	Uiso*/Ueq
C1	0.86901 (12)	0.5813 (3)	0.40834 (15)	0.0629 (4)
H1A	0.9087	0.6247	0.4850	0.094*
H1B	0.9003	0.6280	0.3574	0.094*
H1C	0.8706	0.4501	0.4077	0.094*
C2	0.75619 (10)	0.64523 (16)	0.36931 (11)	0.0420 (2)
C3	0.70532 (11)	0.71403 (19)	0.43482 (11)	0.0472 (3)
H3	0.7381	0.7283	0.5142	0.057*
C4	0.59850 (11)	0.76142 (18)	0.37063 (11)	0.0454 (3)
H4	0.5532	0.8095	0.4031	0.054*
C5	0.56820 (9)	0.72928 (16)	0.25515 (10)	0.0383 (2)
C6	0.46547 (10)	0.76359 (16)	0.16459 (11)	0.0399 (2)
H6	0.4091	0.8003	0.1840	0.048*
C7	0.34681 (10)	0.76957 (16)	−0.02564 (10)	0.0387 (2)
C8	0.25773 (11)	0.68505 (19)	−0.01918 (11)	0.0450 (3)
H8	0.2649	0.6153	0.0452	0.054*
C9	0.15877 (11)	0.7036 (2)	−0.10729 (12)	0.0485 (3)
H9	0.0991	0.6471	−0.1031	0.058*
C10	0.15028 (11)	0.80772 (18)	−0.20170 (11)	0.0449 (3)
C11	0.23669 (12)	0.89611 (19)	−0.20981 (11)	0.0485 (3)
H11	0.2285	0.9684	−0.2734	0.058*
C12	0.33524 (11)	0.87551 (18)	−0.12212 (12)	0.0465 (3)
H12	0.3945	0.9324	−0.1271	0.056*
N1	0.44994 (9)	0.74494 (15)	0.05856 (9)	0.0433 (2)
N2	0.04664 (11)	0.8230 (2)	−0.29732 (11)	0.0588 (3)
O1	0.04178 (11)	0.9053 (2)	−0.38389 (10)	0.0808 (4)
O2	−0.03044 (10)	0.7504 (3)	−0.28855 (12)	0.0869 (4)
S1	0.67202 (2)	0.63767 (4)	0.22616 (3)	0.04172 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0446 (7)	0.0756 (10)	0.0608 (9)	0.0099 (7)	0.0119 (6)	0.0015 (8)
C2	0.0425 (6)	0.0397 (6)	0.0415 (6)	−0.0008 (4)	0.0138 (5)	0.0025 (4)
C3	0.0525 (7)	0.0503 (7)	0.0366 (6)	−0.0037 (5)	0.0149 (5)	−0.0031 (5)
C4	0.0483 (6)	0.0487 (6)	0.0429 (6)	−0.0010 (5)	0.0217 (5)	−0.0063 (5)
C5	0.0395 (5)	0.0359 (5)	0.0411 (5)	−0.0014 (4)	0.0173 (4)	−0.0012 (4)
C6	0.0392 (5)	0.0362 (5)	0.0448 (6)	−0.0008 (4)	0.0167 (5)	−0.0014 (4)
C7	0.0429 (6)	0.0353 (5)	0.0384 (5)	0.0025 (4)	0.0163 (4)	0.0003 (4)
C8	0.0466 (6)	0.0471 (6)	0.0396 (6)	−0.0020 (5)	0.0150 (5)	0.0058 (5)
C9	0.0444 (6)	0.0545 (7)	0.0451 (6)	−0.0036 (5)	0.0154 (5)	0.0009 (6)
C10	0.0472 (6)	0.0467 (6)	0.0360 (5)	0.0078 (5)	0.0108 (5)	−0.0034 (5)
C11	0.0618 (8)	0.0446 (6)	0.0391 (6)	0.0066 (6)	0.0196 (6)	0.0059 (5)
C12	0.0517 (7)	0.0456 (6)	0.0450 (6)	−0.0013 (5)	0.0218 (5)	0.0047 (5)
N1	0.0415 (5)	0.0451 (5)	0.0427 (5)	0.0026 (4)	0.0157 (4)	0.0029 (4)
N2	0.0564 (7)	0.0685 (8)	0.0422 (6)	0.0143 (6)	0.0088 (5)	−0.0060 (6)
O1	0.0834 (9)	0.0975 (10)	0.0456 (6)	0.0223 (7)	0.0075 (6)	0.0146 (6)
O2	0.0499 (7)	0.1314 (13)	0.0642 (8)	0.0002 (8)	0.0054 (6)	0.0030 (8)
S1	0.04364 (17)	0.04606 (17)	0.03761 (15)	0.00209 (12)	0.01807 (12)	−0.00092 (11)

Geometric parameters (Å, º)

C1—H1A	0.9600	C7—C8	1.3901 (18)
C1—H1B	0.9600	C7—C12	1.3977 (17)
C1—H1C	0.9600	C7—N1	1.4045 (16)
C1—C2	1.4935 (19)	C8—H8	0.9300
C2—C3	1.3616 (19)	C8—C9	1.3801 (18)
C2—S1	1.7222 (13)	C9—H9	0.9300
C3—H3	0.9300	C9—C10	1.3788 (19)
C3—C4	1.405 (2)	C10—C11	1.379 (2)
C4—H4	0.9300	C10—N2	1.4612 (18)
C4—C5	1.3698 (17)	C11—H11	0.9300
C5—C6	1.4429 (17)	C11—C12	1.376 (2)
C5—S1	1.7246 (12)	C12—H12	0.9300
C6—H6	0.9300	N2—O1	1.2247 (19)
C6—N1	1.2760 (17)	N2—O2	1.218 (2)
H1A—C1—H1B	109.5	C8—C7—N1	122.47 (11)
H1A—C1—H1C	109.5	C12—C7—N1	118.10 (11)
H1B—C1—H1C	109.5	C7—C8—H8	119.7
C2—C1—H1A	109.5	C9—C8—C7	120.66 (12)
C2—C1—H1B	109.5	C9—C8—H8	119.7
C2—C1—H1C	109.5	C8—C9—H9	120.7
C1—C2—S1	121.10 (11)	C10—C9—C8	118.54 (12)
C3—C2—C1	127.90 (13)	C10—C9—H9	120.7
C3—C2—S1	111.01 (10)	C9—C10—C11	122.24 (12)
C2—C3—H3	123.3	C9—C10—N2	119.02 (13)
C2—C3—C4	113.39 (12)	C11—C10—N2	118.73 (13)
C4—C3—H3	123.3	C10—C11—H11	120.6
C3—C4—H4	123.6	C12—C11—C10	118.84 (12)
C5—C4—C3	112.81 (12)	C12—C11—H11	120.6
C5—C4—H4	123.6	C7—C12—H12	119.8
C4—C5—C6	127.64 (12)	C11—C12—C7	120.37 (13)
C4—C5—S1	110.91 (10)	C11—C12—H12	119.8
C6—C5—S1	121.45 (9)	C6—N1—C7	119.28 (11)
C5—C6—H6	119.1	O1—N2—C10	118.28 (15)
N1—C6—C5	121.75 (11)	O2—N2—C10	118.78 (14)
N1—C6—H6	119.1	O2—N2—O1	122.91 (14)
C8—C7—C12	119.33 (11)	C2—S1—C5	91.88 (6)