N-[(Pyridin-2-yl)meth­yl]thio­phene-2-carboxamide

In the title compound, C₁₁H₁₀N₂OS, the dihedral angle between the thio­phene and pyridine rings is 77.79 (8)°. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generate R₂²(10) loops. The dimers are reinforced by pairs of C—H...N inter­actions and C—H...O inter­actions link the dimers into [010] chains.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.098
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.267 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         15 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         26 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 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
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 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, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

N-[(Pyridin-2-yl)methyl]thiophene-2-carboxamide

Crystal data

C11H10N2OS	F(000) = 456
Mr = 218.27	Dx = 1.426 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.681 (3) Å	Cell parameters from 4931 reflections
b = 8.088 (3) Å	θ = 2.4–27.5°
c = 14.875 (6) Å	µ = 0.29 mm^−1
β = 103.175 (4)°	T = 110 K
V = 1016.8 (7) Å^3	Black, colourless
Z = 4	0.57 × 0.57 × 0.56 mm

Data collection

Bruker APEXII CCD diffractometer	2058 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.041
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 27.6°, θmin = 2.4°
Tmin = 0.539, Tmax = 0.746	h = −11→11
11046 measured reflections	k = −10→10
2319 independent reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0462P)^2 + 0.5739P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2319 reflections	Δρmax = 0.29 e Å^−3
136 parameters	Δρmin = −0.35 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	0.48410 (5)	1.06177 (5)	0.27924 (3)	0.02145 (13)
O1	0.27142 (13)	0.92442 (13)	0.38710 (8)	0.0201 (3)
N1	0.25034 (15)	0.41563 (15)	0.44501 (9)	0.0164 (3)
N2	0.44226 (14)	0.74541 (15)	0.47523 (9)	0.0149 (3)
H2	0.5392	0.7058	0.4897	0.018*
C1	0.20492 (17)	0.57130 (18)	0.45674 (10)	0.0138 (3)
C2	0.05897 (18)	0.63262 (19)	0.41132 (11)	0.0195 (3)
H2A	0.0290	0.7424	0.4224	0.023*
C3	−0.04294 (19)	0.5317 (2)	0.34950 (12)	0.0245 (4)
H3	−0.1432	0.5714	0.3169	0.029*
C4	0.00436 (19)	0.3724 (2)	0.33628 (12)	0.0238 (4)
H4	−0.0625	0.3006	0.2941	0.029*
C5	0.15017 (19)	0.3193 (2)	0.38527 (11)	0.0210 (3)
H5	0.1814	0.2091	0.3763	0.025*
C6	0.32272 (17)	0.68000 (18)	0.52048 (10)	0.0162 (3)
H6A	0.2661	0.7731	0.5418	0.019*
H6B	0.3754	0.6152	0.5754	0.019*
C7	0.40555 (17)	0.86572 (17)	0.41170 (10)	0.0143 (3)
C8	0.53409 (18)	0.92391 (17)	0.36918 (10)	0.0141 (3)
C9	0.69193 (18)	0.88705 (19)	0.38810 (11)	0.0176 (3)
H9	0.7421	0.8136	0.4357	0.021*
C10	0.77229 (19)	0.9712 (2)	0.32843 (11)	0.0213 (3)
H10	0.8824	0.9607	0.3317	0.026*
C11	0.6740 (2)	1.0683 (2)	0.26630 (11)	0.0208 (3)
H11	0.7072	1.1326	0.2207	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0171 (2)	0.0242 (2)	0.0209 (2)	−0.00174 (15)	−0.00019 (15)	0.00863 (15)
O1	0.0139 (5)	0.0177 (6)	0.0278 (6)	0.0023 (4)	0.0029 (5)	0.0045 (4)
N1	0.0146 (6)	0.0150 (6)	0.0199 (7)	0.0009 (5)	0.0046 (5)	0.0026 (5)
N2	0.0101 (6)	0.0151 (6)	0.0194 (6)	−0.0001 (5)	0.0029 (5)	0.0018 (5)
C1	0.0124 (7)	0.0155 (7)	0.0149 (7)	−0.0001 (5)	0.0061 (5)	0.0032 (5)
C2	0.0132 (7)	0.0178 (7)	0.0283 (9)	0.0020 (6)	0.0065 (6)	0.0048 (6)
C3	0.0112 (7)	0.0306 (9)	0.0296 (9)	−0.0014 (6)	0.0003 (6)	0.0080 (7)
C4	0.0194 (8)	0.0268 (9)	0.0236 (8)	−0.0102 (7)	0.0018 (6)	0.0008 (6)
C5	0.0223 (8)	0.0166 (7)	0.0252 (8)	−0.0024 (6)	0.0074 (7)	−0.0013 (6)
C6	0.0158 (7)	0.0168 (7)	0.0172 (7)	−0.0009 (6)	0.0063 (6)	0.0009 (6)
C7	0.0148 (7)	0.0110 (6)	0.0169 (7)	−0.0012 (5)	0.0032 (6)	−0.0025 (5)
C8	0.0175 (7)	0.0112 (6)	0.0131 (7)	−0.0001 (5)	0.0023 (5)	−0.0002 (5)
C9	0.0176 (8)	0.0168 (7)	0.0197 (8)	0.0027 (6)	0.0069 (6)	0.0033 (6)
C10	0.0197 (8)	0.0223 (8)	0.0249 (8)	0.0026 (6)	0.0110 (6)	0.0030 (6)
C11	0.0225 (8)	0.0226 (8)	0.0187 (8)	−0.0036 (6)	0.0075 (6)	0.0030 (6)

Geometric parameters (Å, º)

S1—C8	1.7195 (16)	C3—C4	1.380 (3)
S1—C11	1.7031 (18)	C4—H4	0.9500
O1—C7	1.2331 (18)	C4—C5	1.377 (2)
N1—C1	1.3425 (19)	C5—H5	0.9500
N1—C5	1.342 (2)	C6—H6A	0.9900
N2—H2	0.8800	C6—H6B	0.9900
N2—C6	1.4587 (18)	C7—C8	1.479 (2)
N2—C7	1.3431 (19)	C8—C9	1.367 (2)
C1—C2	1.385 (2)	C9—H9	0.9500
C1—C6	1.509 (2)	C9—C10	1.421 (2)
C2—H2A	0.9500	C10—H10	0.9500
C2—C3	1.387 (2)	C10—C11	1.356 (2)
C3—H3	0.9500	C11—H11	0.9500
C11—S1—C8	91.66 (8)	N2—C6—H6A	109.2
C5—N1—C1	117.73 (13)	N2—C6—H6B	109.2
C6—N2—H2	119.7	C1—C6—H6A	109.2
C7—N2—H2	119.7	C1—C6—H6B	109.2
C7—N2—C6	120.51 (13)	H6A—C6—H6B	107.9
N1—C1—C2	122.39 (14)	O1—C7—N2	122.98 (13)
N1—C1—C6	116.81 (13)	O1—C7—C8	120.25 (13)
C2—C1—C6	120.77 (14)	N2—C7—C8	116.75 (13)
C1—C2—H2A	120.4	C7—C8—S1	117.25 (11)
C1—C2—C3	119.16 (15)	C9—C8—S1	111.40 (11)
C3—C2—H2A	120.4	C9—C8—C7	131.35 (14)
C2—C3—H3	120.7	C8—C9—H9	123.9
C4—C3—C2	118.57 (15)	C8—C9—C10	112.24 (14)
C4—C3—H3	120.7	C10—C9—H9	123.9
C3—C4—H4	120.6	C9—C10—H10	123.8
C5—C4—C3	118.90 (15)	C11—C10—C9	112.37 (15)
C5—C4—H4	120.6	C11—C10—H10	123.8
N1—C5—C4	123.23 (15)	S1—C11—H11	123.8
N1—C5—H5	118.4	C10—C11—S1	112.33 (12)
C4—C5—H5	118.4	C10—C11—H11	123.8
N2—C6—C1	111.90 (12)
S1—C8—C9—C10	−0.32 (17)	C5—N1—C1—C2	1.5 (2)
O1—C7—C8—S1	−5.13 (19)	C5—N1—C1—C6	−176.95 (13)
O1—C7—C8—C9	175.25 (15)	C6—N2—C7—O1	−1.4 (2)
N1—C1—C2—C3	−1.8 (2)	C6—N2—C7—C8	−179.75 (12)
N1—C1—C6—N2	79.64 (16)	C6—C1—C2—C3	176.59 (14)
N2—C7—C8—S1	173.26 (11)	C7—N2—C6—C1	73.47 (17)
N2—C7—C8—C9	−6.4 (2)	C7—C8—C9—C10	179.31 (15)
C1—N1—C5—C4	−0.2 (2)	C8—S1—C11—C10	−0.70 (13)
C1—C2—C3—C4	0.8 (2)	C8—C9—C10—C11	−0.2 (2)
C2—C1—C6—N2	−98.81 (16)	C9—C10—C11—S1	0.64 (19)
C2—C3—C4—C5	0.4 (2)	C11—S1—C8—C7	−179.12 (12)
C3—C4—C5—N1	−0.7 (2)	C11—S1—C8—C9	0.58 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1^i	0.88	2.11	2.963 (2)	164
C5—H5···O1^ii	0.95	2.43	3.361 (2)	168
C9—H9···N1^i	0.95	2.56	3.441 (2)	155

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