Salicyl-aldehyde-4-(dimethyl-amino)-pyridine (1/1).

In the title compound, C(7)H(10)N(2)·C(7)H(6)O(2), the components are linked by an O-H⋯N hydrogen bond. The mean planes of two mol-ecules form a dihedral angle of 78.68 (5)°. The crystal packing exhibits weak non-classical C-H⋯O contacts.

Related literature

For background to hydrogen bonding in crystal engineering, see: Bosch (2010 ▶); Desiraju (1989 ▶); Lehn (1995 ▶). For related structures, see: Bosch (2010 ▶); Vembu et al. (2003 ▶); Lo & Ng (2009 ▶).

Experimental

Crystal data

C7H10N2·C7H6O2

M = 244.29

Triclinic,

a = 7.540 (3) Å

b = 8.473 (3) Å

c = 10.413 (4) Å

α = 85.370 (11)°

β = 77.371 (10)°

γ = 87.203 (10)°

V = 646.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.4 × 0.4 × 0.38 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.967, T max = 0.968

4199 measured reflections

2913 independent reflections

1882 reflections with I > 2σ(I)

R int = 0.02

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.163

S = 1.01

2913 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034185/cv2756sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034185/cv2756Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H10N2·C7H6O2	Z = 2
Mr = 244.29	F(000) = 260
Triclinic, P1	Dx = 1.255 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.540 (3) Å	Cell parameters from 1563 reflections
b = 8.473 (3) Å	θ = 2.8–27.8°
c = 10.413 (4) Å	µ = 0.09 mm−1
α = 85.370 (11)°	T = 296 K
β = 77.371 (10)°	Prism, yellow
γ = 87.203 (10)°	0.4 × 0.4 × 0.38 mm
V = 646.7 (4) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2913 independent reflections
Radiation source: Mo Kα	1882 reflections with I > 2σ(I)
graphite	Rint = 0.02
φ and ω scans	θmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→9
Tmin = 0.967, Tmax = 0.968	k = −5→11
4199 measured reflections	l = −13→13

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0815P)2 + 0.0644P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.163	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.20 e Å−3
2913 reflections	Δρmin = −0.15 e Å−3
166 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.8429 (3)	0.2372 (2)	0.5097 (2)	0.0720 (5)
H1	0.868	0.1401	0.5513	0.086*
C2	0.7810 (3)	0.3587 (2)	0.58701 (17)	0.0638 (5)
H2	0.7635	0.3422	0.6782	0.077*
C3	0.7433 (2)	0.5084 (2)	0.52993 (15)	0.0521 (4)
C4	0.7680 (2)	0.5182 (2)	0.39168 (16)	0.0604 (4)
H4	0.7426	0.6132	0.3469	0.072*
C5	0.8288 (3)	0.3893 (3)	0.32350 (18)	0.0693 (5)
H5	0.8428	0.4003	0.2323	0.083*
C6	0.6562 (3)	0.6217 (3)	0.74452 (19)	0.0879 (7)
H6A	0.5548	0.5552	0.7795	0.132*
H6B	0.6298	0.725	0.777	0.132*
H6C	0.7624	0.5762	0.7717	0.132*
C7	0.6590 (3)	0.7888 (3)	0.5390 (2)	0.0798 (6)
H7A	0.7616	0.8131	0.4686	0.12*
H7B	0.6445	0.8672	0.6024	0.12*
H7C	0.5513	0.7885	0.5041	0.12*
C8	0.9510 (2)	−0.18638 (19)	0.10290 (14)	0.0500 (4)
C9	0.8248 (3)	−0.2663 (2)	0.05460 (16)	0.0603 (5)
H9	0.8641	−0.3511	0.0029	0.072*
C10	0.6437 (3)	−0.2223 (3)	0.08184 (19)	0.0724 (5)
H10	0.5604	−0.2764	0.0493	0.087*
C11	0.5875 (3)	−0.0964 (3)	0.1584 (2)	0.0754 (6)
H11	0.4652	−0.065	0.1763	0.09*
C12	0.7082 (2)	−0.0158 (2)	0.20895 (18)	0.0654 (5)
H12	0.6669	0.0687	0.2605	0.078*
C13	0.8914 (2)	−0.06070 (19)	0.18288 (14)	0.0515 (4)
C14	1.1435 (3)	−0.2309 (2)	0.06846 (17)	0.0631 (5)
H14	1.2235	−0.1669	0.0951	0.076*
N1	0.8703 (2)	0.2475 (2)	0.37777 (17)	0.0724 (5)
N2	0.6887 (2)	0.63491 (19)	0.60206 (13)	0.0636 (4)
O1	1.2084 (2)	−0.34318 (19)	0.00855 (16)	0.0891 (5)
O2	1.01269 (17)	0.01257 (16)	0.23295 (13)	0.0670 (4)
H2A	0.961	0.0844	0.2765	0.101*

	U11	U22	U33	U12	U13	U23
C1	0.0818 (13)	0.0592 (12)	0.0816 (13)	−0.0101 (9)	−0.0299 (10)	−0.0061 (9)
C2	0.0763 (12)	0.0654 (12)	0.0532 (9)	−0.0126 (9)	−0.0203 (8)	−0.0007 (8)
C3	0.0488 (8)	0.0622 (11)	0.0477 (8)	−0.0119 (7)	−0.0121 (7)	−0.0073 (7)
C4	0.0678 (10)	0.0654 (11)	0.0503 (9)	−0.0068 (8)	−0.0163 (8)	−0.0055 (8)
C5	0.0764 (12)	0.0813 (15)	0.0542 (10)	−0.0080 (10)	−0.0162 (9)	−0.0188 (9)
C6	0.1038 (16)	0.1054 (19)	0.0546 (11)	0.0003 (13)	−0.0119 (10)	−0.0232 (11)
C7	0.0877 (14)	0.0677 (14)	0.0813 (13)	0.0053 (10)	−0.0114 (11)	−0.0126 (10)
C8	0.0633 (10)	0.0484 (9)	0.0393 (7)	−0.0072 (7)	−0.0137 (7)	0.0023 (6)
C9	0.0776 (12)	0.0578 (11)	0.0483 (9)	−0.0128 (8)	−0.0154 (8)	−0.0085 (7)
C10	0.0688 (12)	0.0883 (15)	0.0667 (11)	−0.0241 (10)	−0.0209 (9)	−0.0136 (10)
C11	0.0588 (11)	0.0952 (16)	0.0755 (12)	−0.0095 (10)	−0.0163 (9)	−0.0173 (11)
C12	0.0636 (11)	0.0681 (12)	0.0668 (11)	−0.0022 (9)	−0.0141 (8)	−0.0187 (9)
C13	0.0615 (10)	0.0502 (9)	0.0455 (8)	−0.0089 (7)	−0.0170 (7)	−0.0008 (7)
C14	0.0698 (11)	0.0637 (12)	0.0600 (10)	−0.0001 (9)	−0.0218 (8)	−0.0105 (8)
N1	0.0745 (10)	0.0704 (12)	0.0794 (11)	−0.0065 (8)	−0.0232 (8)	−0.0264 (8)
N2	0.0734 (9)	0.0667 (10)	0.0507 (8)	−0.0049 (7)	−0.0103 (7)	−0.0114 (7)
O1	0.0889 (10)	0.0822 (11)	0.1002 (11)	0.0161 (8)	−0.0239 (8)	−0.0325 (8)
O2	0.0665 (8)	0.0665 (9)	0.0756 (8)	−0.0047 (6)	−0.0244 (6)	−0.0235 (6)

C1—N1	1.340 (3)	C7—H7B	0.96
C1—C2	1.359 (3)	C7—H7C	0.96
C1—H1	0.93	C8—C9	1.394 (2)
C2—C3	1.400 (3)	C8—C13	1.401 (2)
C2—H2	0.93	C8—C14	1.455 (3)
C3—N2	1.355 (2)	C9—C10	1.372 (3)
C3—C4	1.407 (2)	C9—H9	0.93
C4—C5	1.357 (3)	C10—C11	1.378 (3)
C4—H4	0.93	C10—H10	0.93
C5—N1	1.339 (3)	C11—C12	1.378 (3)
C5—H5	0.93	C11—H11	0.93
C6—N2	1.446 (2)	C12—C13	1.389 (3)
C6—H6A	0.96	C12—H12	0.93
C6—H6B	0.96	C13—O2	1.3452 (18)
C6—H6C	0.96	C14—O1	1.205 (2)
C7—N2	1.442 (3)	C14—H14	0.93
C7—H7A	0.96	O2—H2A	0.82
N1—C1—C2	124.69 (19)	C9—C8—C13	119.44 (16)
N1—C1—H1	117.7	C9—C8—C14	120.36 (16)
C2—C1—H1	117.7	C13—C8—C14	120.19 (14)
C1—C2—C3	120.29 (17)	C10—C9—C8	121.25 (17)
C1—C2—H2	119.9	C10—C9—H9	119.4
C3—C2—H2	119.9	C8—C9—H9	119.4
N2—C3—C2	122.62 (15)	C9—C10—C11	118.68 (17)
N2—C3—C4	122.36 (16)	C9—C10—H10	120.7
C2—C3—C4	115.02 (16)	C11—C10—H10	120.7
C5—C4—C3	120.10 (18)	C10—C11—C12	121.63 (19)
C5—C4—H4	120	C10—C11—H11	119.2
C3—C4—H4	120	C12—C11—H11	119.2
N1—C5—C4	124.86 (17)	C11—C12—C13	119.98 (18)
N1—C5—H5	117.6	C11—C12—H12	120
C4—C5—H5	117.6	C13—C12—H12	120
N2—C6—H6A	109.5	O2—C13—C12	121.78 (16)
N2—C6—H6B	109.5	O2—C13—C8	119.24 (15)
H6A—C6—H6B	109.5	C12—C13—C8	118.99 (15)
N2—C6—H6C	109.5	O1—C14—C8	125.87 (17)
H6A—C6—H6C	109.5	O1—C14—H14	117.1
H6B—C6—H6C	109.5	C8—C14—H14	117.1
N2—C7—H7A	109.5	C5—N1—C1	114.99 (16)
N2—C7—H7B	109.5	C3—N2—C7	120.92 (15)
H7A—C7—H7B	109.5	C3—N2—C6	121.81 (17)
N2—C7—H7C	109.5	C7—N2—C6	117.26 (16)
H7A—C7—H7C	109.5	C13—O2—H2A	109.5
H7B—C7—H7C	109.5
N1—C1—C2—C3	−1.0 (3)	C9—C8—C13—O2	177.74 (14)
C1—C2—C3—N2	−177.17 (16)	C14—C8—C13—O2	−3.5 (2)
C1—C2—C3—C4	2.3 (2)	C9—C8—C13—C12	−1.9 (2)
N2—C3—C4—C5	177.77 (16)	C14—C8—C13—C12	176.90 (16)
C2—C3—C4—C5	−1.7 (2)	C9—C8—C14—O1	−6.8 (3)
C3—C4—C5—N1	−0.3 (3)	C13—C8—C14—O1	174.44 (18)
C13—C8—C9—C10	1.3 (2)	C4—C5—N1—C1	1.7 (3)
C14—C8—C9—C10	−177.51 (16)	C2—C1—N1—C5	−1.1 (3)
C8—C9—C10—C11	0.1 (3)	C2—C3—N2—C7	177.21 (17)
C9—C10—C11—C12	−0.8 (3)	C4—C3—N2—C7	−2.2 (3)
C10—C11—C12—C13	0.2 (3)	C2—C3—N2—C6	−3.3 (3)
C11—C12—C13—O2	−178.43 (16)	C4—C3—N2—C6	177.28 (17)
C11—C12—C13—C8	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1	0.82	1.82	2.637 (2)	174
C9—H9···O1i	0.93	2.69	3.456 (3)	140
C5—H5···O1ii	0.93	2.7	3.583 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1	0.82	1.82	2.637 (2)	174
C9—H9⋯O1i	0.93	2.69	3.456 (3)	140
C5—H5⋯O1ii	0.93	2.7	3.583 (3)	158

Symmetry codes: (i) ; (ii) .