2-Furan­carboxanilide

In the title compound, N-phenyl­furan-2-carbox­amide, C₁₁H₉NO₂, the C=O group is anti in relation to the amide NH group. The phenyl ring is twisted by 147.67 (14)° about the C(phenyl)—N bond with respect to the planar 2-fur­amide fragment. The amide H atom is the donor in a bifurcated hydrogen bond involving an intramolecular N—H...O [2.682 (2) Å] interaction with the furan O atom and an intermolecular N—H...O hydrogen bond [3.084 (2) Å] with the amide O atom. According to the graph-set assignment, the intramolecular hydrogen-bond pattern is of the S(5) type. The intermolecular N—H...O hydrogen bond links the mol­ecules into infinite C(4) chains along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.050
• wR factor = 0.130
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.64 mm
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON98 (Spek, 1998); software used to prepare material for publication: SHELXL97.

N-phenylfuran-2-carboxamide

Crystal data

C11H9NO2	Dx = 1.318 Mg m^−3
Mr = 187.19	Melting point = 396–397 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5046 reflections
a = 8.699 (2) Å	θ = 15–27°
b = 12.983 (2) Å	µ = 0.09 mm^−1
c = 16.712 (2) Å	T = 296 K
V = 1887.4 (5) Å^3	Prism, colourless
Z = 8	0.64 × 0.51 × 0.42 mm
F(000) = 784

Data collection

Oxford Diffraction Xcalibur2 diffractometer with Sapphire 3 CCD detector	1758 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite parallel monochromator	θmax = 26.5°, θmin = 4.6°
φ and ω scans	h = −10→10
32112 measured reflections	k = −16→16
1903 independent reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: geom & difmap
wR(F^2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0753P)^2 + 0.0157P] where P = (Fo^2 + 2Fc^2)/3
1903 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.01579 (12)	0.23504 (9)	0.17519 (6)	0.0489 (3)
O2	0.39457 (12)	0.13439 (10)	0.16041 (7)	0.0551 (4)
N	0.20672 (15)	0.10881 (10)	0.25433 (7)	0.0425 (3)
H1N	0.116 (2)	0.1250 (14)	0.2682 (11)	0.054 (5)*
C1	0.15826 (16)	0.21861 (11)	0.14299 (9)	0.0399 (4)
C2	0.17223 (19)	0.27172 (14)	0.07415 (10)	0.0527 (4)
H2	0.2577	0.2735	0.0407	0.063*
C3	0.0314 (2)	0.32436 (14)	0.06263 (10)	0.0570 (5)
H3	0.0063	0.3674	0.0201	0.068*
C4	−0.0578 (2)	0.30038 (13)	0.12434 (10)	0.0538 (4)
H4	−0.1573	0.3249	0.1318	0.065*
C5	0.26397 (17)	0.14961 (11)	0.18630 (8)	0.0402 (4)
C6	0.28327 (16)	0.04057 (11)	0.30710 (9)	0.0397 (4)
C7	0.24840 (18)	0.04681 (12)	0.38803 (9)	0.0483 (4)
H7	0.1769	0.0949	0.4058	0.058*
C8	0.3190 (2)	−0.01771 (15)	0.44211 (11)	0.0577 (5)
H8	0.2948	−0.0133	0.4962	0.069*
C9	0.4255 (2)	−0.08887 (14)	0.41620 (11)	0.0609 (5)
H9	0.4746	−0.1316	0.4528	0.073*
C10	0.4590 (2)	−0.09649 (14)	0.33579 (11)	0.0577 (5)
H10	0.5302	−0.1450	0.3184	0.069*
C11	0.38778 (18)	−0.03252 (12)	0.28042 (11)	0.0492 (4)
H11	0.4098	−0.0386	0.2262	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0375 (6)	0.0579 (7)	0.0513 (7)	0.0089 (5)	0.0039 (4)	0.0106 (5)
O2	0.0359 (6)	0.0736 (8)	0.0558 (7)	0.0095 (5)	0.0076 (5)	0.0099 (5)
N	0.0312 (7)	0.0512 (8)	0.0451 (7)	0.0068 (5)	0.0030 (5)	0.0046 (5)
C1	0.0317 (7)	0.0449 (8)	0.0432 (8)	−0.0011 (6)	−0.0006 (6)	−0.0030 (6)
C2	0.0443 (9)	0.0667 (10)	0.0472 (9)	0.0021 (7)	0.0051 (7)	0.0093 (7)
C3	0.0541 (10)	0.0638 (11)	0.0530 (9)	0.0072 (8)	−0.0018 (8)	0.0150 (8)
C4	0.0428 (9)	0.0583 (10)	0.0604 (10)	0.0114 (7)	−0.0027 (7)	0.0098 (8)
C5	0.0341 (8)	0.0446 (8)	0.0418 (7)	0.0004 (6)	−0.0012 (6)	−0.0026 (6)
C6	0.0326 (7)	0.0420 (7)	0.0444 (8)	−0.0023 (6)	−0.0028 (6)	0.0012 (6)
C7	0.0449 (8)	0.0531 (9)	0.0470 (9)	−0.0009 (7)	−0.0029 (6)	−0.0039 (7)
C8	0.0570 (10)	0.0687 (11)	0.0475 (9)	−0.0080 (9)	−0.0104 (7)	0.0038 (8)
C9	0.0514 (10)	0.0630 (11)	0.0684 (11)	−0.0034 (8)	−0.0202 (9)	0.0165 (9)
C10	0.0447 (9)	0.0517 (9)	0.0767 (12)	0.0085 (8)	−0.0040 (8)	0.0064 (8)
C11	0.0443 (8)	0.0493 (8)	0.0540 (9)	0.0053 (7)	0.0017 (7)	0.0010 (7)

Geometric parameters (Å, º)

O1—C4	1.361 (2)	C4—H4	0.9300
O1—C1	1.368 (2)	C6—C11	1.388 (2)
O2—C5	1.232 (2)	C6—C7	1.388 (2)
N—C5	1.349 (2)	C7—C8	1.377 (2)
N—C6	1.416 (2)	C7—H7	0.9300
N—H1N	0.85 (2)	C8—C9	1.378 (3)
C1—C2	1.347 (2)	C8—H8	0.9300
C1—C5	1.474 (2)	C9—C10	1.379 (3)
C2—C3	1.416 (3)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.389 (2)
C3—C4	1.328 (2)	C10—H10	0.9300
C3—H3	0.9300	C11—H11	0.9300
C4—O1—C1	106.14 (12)	C11—C6—C7	119.74 (15)
C5—N—C6	126.6 (2)	C11—C6—N	122.38 (14)
C5—N—H1N	118.4 (12)	C7—C6—N	117.87 (13)
C6—N—H1N	114.9 (12)	C8—C7—C6	120.43 (16)
C2—C1—O1	109.75 (13)	C8—C7—H7	119.8
C2—C1—C5	132.42 (14)	C6—C7—H7	119.8
O1—C1—C5	117.83 (12)	C7—C8—C9	120.09 (16)
C1—C2—C3	106.58 (14)	C7—C8—H8	120.0
C1—C2—H2	126.7	C9—C8—H8	120.0
C3—C2—H2	126.7	C8—C9—C10	119.77 (16)
C4—C3—C2	106.68 (14)	C8—C9—H9	120.1
C4—C3—H3	126.7	C10—C9—H9	120.1
C2—C3—H3	126.7	C9—C10—C11	120.80 (17)
C3—C4—O1	110.85 (14)	C9—C10—H10	119.6
C3—C4—H4	124.6	C11—C10—H10	119.6
O1—C4—H4	124.6	C6—C11—C10	119.14 (16)
O2—C5—N	124.98 (14)	C6—C11—H11	120.4
O2—C5—C1	120.04 (13)	C10—C11—H11	120.4
N—C5—C1	114.97 (13)
C4—O1—C1—C2	−0.28 (17)	O1—C1—C5—N	0.40 (19)
C4—O1—C1—C5	−179.91 (13)	C5—N—C6—C11	−33.7 (2)
O1—C1—C2—C3	0.13 (18)	C5—N—C6—C7	147.67 (14)
C5—C1—C2—C3	179.69 (16)	C11—C6—C7—C8	1.2 (2)
C1—C2—C3—C4	0.1 (2)	N—C6—C7—C8	179.86 (14)
C2—C3—C4—O1	−0.3 (2)	C6—C7—C8—C9	0.3 (2)
C1—O1—C4—C3	0.33 (19)	C7—C8—C9—C10	−1.2 (3)
C6—N—C5—O2	−1.2 (2)	C8—C9—C10—C11	0.6 (3)
C6—N—C5—C1	−179.99 (13)	C7—C6—C11—C10	−1.8 (2)
C2—C1—C5—O2	2.0 (3)	N—C6—C11—C10	179.67 (14)
O1—C1—C5—O2	−178.42 (13)	C9—C10—C11—C6	0.8 (3)
C2—C1—C5—N	−179.13 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H1N···O1	0.85 (2)	2.28 (2)	2.682 (2)	109 (2)
N—H1N···O2^i	0.85 (2)	2.27 (2)	3.084 (2)	161 (2)

Symmetry code: (i) x−1/2, y, −z+1/2.