N-(4-Chloro­phen­yl)picolinamide

The title mol­ecule, C₁₂H₉ClN₂O, is almost planar. Inter­molecular C—H...O hydrogen bonds link the mol­ecules into chains along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.125
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

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Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

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

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

N-(4-Chlorophenyl)picolinamide

Crystal data

C12H9ClN2O	Z = 2
Mr = 232.66	F(000) = 240
Triclinic, P1	Dx = 1.416 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.308 (3) Å	Cell parameters from 1672 reflections
b = 8.251 (3) Å	θ = 2.5–27.9°
c = 10.766 (4) Å	µ = 0.33 mm^−1
α = 87.358 (4)°	T = 291 K
β = 86.463 (4)°	Block, colourless
γ = 77.518 (4)°	0.50 × 0.40 × 0.26 mm
V = 545.8 (4) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	1940 independent reflections
Radiation source: fine-focus sealed tube	1294 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.853, Tmax = 0.921	k = −9→9
3842 measured reflections	l = −12→13

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0698P)^2] where P = (Fo^2 + 2Fc^2)/3
1940 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.12203 (12)	1.25338 (9)	0.01215 (6)	0.0827 (3)
O1	0.7745 (3)	0.7569 (2)	0.43248 (15)	0.0620 (5)
N1	0.4036 (3)	0.8162 (2)	0.44913 (16)	0.0467 (5)
H1N	0.2962	0.7968	0.4963	0.056*
N2	0.4052 (3)	0.6279 (2)	0.65694 (18)	0.0536 (5)
C1	0.4042 (4)	0.5333 (3)	0.7615 (2)	0.0626 (7)
H1	0.2707	0.5281	0.8015	0.075*
C2	0.5884 (5)	0.4440 (3)	0.8127 (2)	0.0639 (7)
H2	0.5792	0.3792	0.8851	0.077*
C3	0.7869 (4)	0.4514 (3)	0.7559 (2)	0.0616 (6)
H3	0.9144	0.3915	0.7889	0.074*
C4	0.7944 (4)	0.5493 (3)	0.6489 (2)	0.0526 (6)
H4	0.9267	0.5573	0.6087	0.063*
C5	0.6001 (3)	0.6353 (2)	0.60292 (18)	0.0426 (5)
C6	0.6036 (3)	0.7419 (2)	0.48680 (19)	0.0437 (5)
C7	0.3465 (3)	0.9203 (2)	0.34434 (19)	0.0418 (5)
C8	0.1255 (4)	0.9765 (3)	0.3257 (2)	0.0521 (6)
H8	0.0229	0.9453	0.3823	0.063*
C9	0.0580 (4)	1.0777 (3)	0.2245 (2)	0.0578 (6)
H9	−0.0896	1.1147	0.2127	0.069*
C10	0.2095 (4)	1.1244 (3)	0.1401 (2)	0.0503 (6)
C11	0.4282 (4)	1.0693 (3)	0.1566 (2)	0.0523 (6)
H11	0.5297	1.1005	0.0993	0.063*
C12	0.4970 (4)	0.9681 (3)	0.2579 (2)	0.0493 (5)
H12	0.6450	0.9313	0.2688	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0812 (5)	0.0987 (6)	0.0619 (4)	−0.0084 (4)	−0.0165 (3)	0.0312 (4)
O1	0.0402 (9)	0.0773 (11)	0.0657 (10)	−0.0126 (8)	0.0019 (8)	0.0209 (8)
N1	0.0365 (10)	0.0522 (11)	0.0505 (10)	−0.0118 (8)	0.0026 (8)	0.0122 (8)
N2	0.0490 (11)	0.0564 (11)	0.0556 (11)	−0.0156 (9)	0.0011 (9)	0.0106 (9)
C1	0.0609 (16)	0.0689 (16)	0.0587 (14)	−0.0215 (13)	0.0054 (12)	0.0154 (12)
C2	0.0834 (19)	0.0601 (15)	0.0513 (13)	−0.0247 (13)	−0.0089 (13)	0.0161 (11)
C3	0.0636 (16)	0.0604 (15)	0.0603 (15)	−0.0109 (12)	−0.0189 (12)	0.0127 (12)
C4	0.0468 (13)	0.0574 (14)	0.0528 (13)	−0.0095 (10)	−0.0060 (10)	0.0050 (11)
C5	0.0450 (12)	0.0408 (11)	0.0428 (11)	−0.0113 (9)	−0.0014 (9)	−0.0002 (9)
C6	0.0403 (12)	0.0421 (12)	0.0479 (12)	−0.0084 (9)	0.0011 (9)	0.0011 (9)
C7	0.0391 (11)	0.0437 (12)	0.0438 (11)	−0.0131 (9)	−0.0007 (9)	0.0026 (9)
C8	0.0370 (12)	0.0609 (14)	0.0587 (13)	−0.0146 (10)	0.0015 (10)	0.0096 (11)
C9	0.0411 (13)	0.0671 (15)	0.0635 (14)	−0.0092 (11)	−0.0089 (11)	0.0111 (12)
C10	0.0530 (14)	0.0532 (13)	0.0453 (12)	−0.0126 (10)	−0.0082 (10)	0.0060 (10)
C11	0.0495 (14)	0.0631 (14)	0.0461 (12)	−0.0193 (11)	−0.0011 (10)	0.0102 (11)
C12	0.0367 (11)	0.0577 (13)	0.0529 (12)	−0.0114 (10)	−0.0007 (9)	0.0077 (10)

Geometric parameters (Å, º)

Cl1—C10	1.743 (2)	C4—C5	1.385 (3)
O1—C6	1.222 (3)	C4—H4	0.93
N1—C6	1.356 (3)	C5—C6	1.497 (3)
N1—C7	1.402 (3)	C7—C12	1.393 (3)
N1—H1N	0.86	C7—C8	1.395 (3)
N2—C5	1.340 (3)	C8—C9	1.373 (3)
N2—C1	1.341 (3)	C8—H8	0.93
C1—C2	1.366 (4)	C9—C10	1.381 (3)
C1—H1	0.93	C9—H9	0.93
C2—C3	1.372 (4)	C10—C11	1.376 (3)
C2—H2	0.93	C11—C12	1.376 (3)
C3—C4	1.380 (3)	C11—H11	0.93
C3—H3	0.93	C12—H12	0.93
C6—N1—C7	129.36 (17)	O1—C6—C5	121.45 (19)
C6—N1—H1N	115.3	N1—C6—C5	114.05 (18)
C7—N1—H1N	115.3	C12—C7—C8	118.7 (2)
C5—N2—C1	116.7 (2)	C12—C7—N1	123.87 (19)
N2—C1—C2	123.7 (2)	C8—C7—N1	117.46 (18)
N2—C1—H1	118.2	C9—C8—C7	120.5 (2)
C2—C1—H1	118.2	C9—C8—H8	119.7
C1—C2—C3	119.0 (2)	C7—C8—H8	119.7
C1—C2—H2	120.5	C8—C9—C10	120.0 (2)
C3—C2—H2	120.5	C8—C9—H9	120.0
C2—C3—C4	118.9 (2)	C10—C9—H9	120.0
C2—C3—H3	120.5	C11—C10—C9	120.2 (2)
C4—C3—H3	120.5	C11—C10—Cl1	120.17 (17)
C3—C4—C5	118.4 (2)	C9—C10—Cl1	119.60 (18)
C3—C4—H4	120.8	C10—C11—C12	120.1 (2)
C5—C4—H4	120.8	C10—C11—H11	120.0
N2—C5—C4	123.2 (2)	C12—C11—H11	120.0
N2—C5—C6	117.29 (19)	C11—C12—C7	120.5 (2)
C4—C5—C6	119.47 (19)	C11—C12—H12	119.8
O1—C6—N1	124.5 (2)	C7—C12—H12	119.8
C5—N2—C1—C2	−1.3 (4)	C4—C5—C6—N1	178.33 (17)
N2—C1—C2—C3	0.7 (4)	C6—N1—C7—C12	−1.0 (3)
C1—C2—C3—C4	0.2 (4)	C6—N1—C7—C8	178.18 (19)
C2—C3—C4—C5	−0.4 (3)	C12—C7—C8—C9	−0.3 (3)
C1—N2—C5—C4	1.0 (3)	N1—C7—C8—C9	−179.48 (19)
C1—N2—C5—C6	−179.37 (19)	C7—C8—C9—C10	0.0 (4)
C3—C4—C5—N2	−0.2 (3)	C8—C9—C10—C11	0.3 (4)
C3—C4—C5—C6	−179.81 (18)	C8—C9—C10—Cl1	−179.80 (18)
C7—N1—C6—O1	0.9 (4)	C9—C10—C11—C12	−0.4 (3)
C7—N1—C6—C5	−178.50 (17)	Cl1—C10—C11—C12	179.73 (16)
N2—C5—C6—O1	179.22 (19)	C10—C11—C12—C7	0.1 (3)
C4—C5—C6—O1	−1.1 (3)	C8—C7—C12—C11	0.2 (3)
N2—C5—C6—N1	−1.3 (3)	N1—C7—C12—C11	179.36 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2	0.86	2.22	2.664 (3)	112
C8—H8···O1^i	0.93	2.46	3.276 (3)	147

Symmetry code: (i) x−1, y, z.