4-(Dimethyl-amino)benzaldehyde.

The title compound, C(9)H(11)NO, crystallizes with two independent but essentially identical mol-ecules in the asymmetric unit, which are linked via a C-H⋯π inter-action. In both mol-ecules, the aldehyde and dimethyl-amine groups are essentially coplanar with the attached benzene ring. In the crystal structure, C-H⋯O hydrogen bonds link one type of independent mol-ecules into a chain along the a axis. In addition, the structure is stabilized by π-π stacking inter-actions involving the benzene rings [centroid-to-centroid distance = 3.697 (2) Å].

Related literature

For synthesis, see: Wu & Zhou (2005 ▶). For general background, see: Kawski et al. (2007 ▶). For related structures, see: Reffner & McCrone (1959 ▶); Dattagupta & Saha (1973 ▶); Herbstein et al. (1984 ▶); Mahadevan et al. (1982 ▶); Habibi et al. (2007 ▶).

Experimental

Crystal data

C9H11NO

M = 149.19

Monoclinic,

a = 10.356 (6) Å

b = 7.686 (4) Å

c = 20.8434 (13) Å

β = 96.808 (13)°

V = 1647.4 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 123 (2) K

0.27 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.979, T max = 0.981

9835 measured reflections

2869 independent reflections

1826 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.160

S = 1.01

2869 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801581X/ci2602sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801581X/ci2602Isup2.hkl

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

C9H11NO	F(000) = 640
Mr = 149.19	Dx = 1.203 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2869 reflections
a = 10.356 (6) Å	θ = 2–25.0°
b = 7.686 (4) Å	µ = 0.08 mm−1
c = 20.8434 (13) Å	T = 123 K
β = 96.808 (13)°	Block, colourless
V = 1647.4 (12) Å3	0.27 × 0.23 × 0.20 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	2869 independent reflections
Radiation source: fine-focus sealed tube	1826 reflections with I > 2σ(I)
graphite	Rint = 0.058
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.979, Tmax = 0.981	k = −9→9
9835 measured reflections	l = −22→24

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0934P)2] where P = (Fo2 + 2Fc2)/3
2869 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	1.26881 (13)	0.5751 (2)	0.18550 (9)	0.1025 (6)
O2	1.37916 (14)	0.2647 (3)	0.04689 (9)	0.1088 (6)
C9	0.57238 (17)	0.7676 (3)	0.21132 (10)	0.0742 (6)
H9A	0.4815	0.7498	0.1976	0.111*
H9B	0.5939	0.8876	0.2055	0.111*
H9C	0.5912	0.7373	0.2561	0.111*
C8	0.57965 (16)	0.5577 (3)	0.12110 (9)	0.0653 (5)
H8A	0.4876	0.5723	0.1213	0.098*
H8B	0.6017	0.4370	0.1271	0.098*
H8C	0.6040	0.5968	0.0805	0.098*
C18	0.69062 (19)	0.0550 (3)	0.08262 (11)	0.0809 (6)
H18A	0.5991	0.0674	0.0694	0.121*
H18B	0.7102	0.0920	0.1267	0.121*
H18C	0.7151	−0.0647	0.0789	0.121*
C17	0.68913 (18)	0.2440 (3)	−0.01380 (10)	0.0776 (6)
H17A	0.5978	0.2267	−0.0120	0.116*
H17B	0.7132	0.1938	−0.0528	0.116*
H17C	0.7079	0.3664	−0.0132	0.116*
C5	0.78138 (15)	0.66025 (19)	0.18319 (8)	0.0453 (4)
C2	1.05546 (16)	0.6610 (2)	0.20311 (9)	0.0524 (5)
N1	0.64859 (12)	0.65921 (18)	0.17319 (7)	0.0542 (4)
C4	0.85497 (16)	0.5535 (2)	0.14644 (8)	0.0508 (4)
H4	0.8126	0.4817	0.1147	0.061*
C3	0.98899 (16)	0.5538 (2)	0.15671 (8)	0.0528 (5)
H3	1.0356	0.4810	0.1322	0.063*
C6	0.84982 (16)	0.7670 (2)	0.23045 (8)	0.0529 (5)
H6	0.8042	0.8385	0.2559	0.063*
C7	0.98356 (16)	0.7666 (2)	0.23942 (8)	0.0559 (5)
H7	1.0268	0.8391	0.2706	0.067*
C1	1.19714 (19)	0.6632 (3)	0.21338 (11)	0.0716 (6)
H1	1.2358	0.7399	0.2444	0.086*
C14	0.89524 (16)	0.1659 (2)	0.05031 (8)	0.0500 (4)
N2	0.76244 (14)	0.1612 (2)	0.04153 (8)	0.0629 (5)
C13	0.96580 (17)	0.2560 (2)	0.00770 (8)	0.0567 (5)
H13	0.9217	0.3114	−0.0281	0.068*
C11	1.16899 (17)	0.1858 (2)	0.07077 (10)	0.0583 (5)
C15	0.96619 (17)	0.0836 (2)	0.10370 (9)	0.0581 (5)
H15	0.9226	0.0210	0.1327	0.070*
C16	1.09953 (17)	0.0953 (2)	0.11309 (9)	0.0609 (5)
H16	1.1446	0.0410	0.1488	0.073*
C12	1.09922 (18)	0.2640 (2)	0.01775 (9)	0.0612 (5)
H12	1.1437	0.3234	−0.0117	0.073*
C10	1.3101 (2)	0.1939 (3)	0.08206 (12)	0.0812 (6)
H10	1.3506	0.1406	0.1192	0.097*

	U11	U22	U33	U12	U13	U23
O1	0.0548 (8)	0.1082 (13)	0.1464 (15)	0.0050 (8)	0.0195 (9)	−0.0127 (11)
O2	0.0684 (10)	0.1282 (15)	0.1327 (15)	−0.0202 (9)	0.0242 (10)	−0.0258 (12)
C9	0.0562 (11)	0.0765 (14)	0.0926 (15)	−0.0019 (10)	0.0201 (11)	−0.0170 (12)
C8	0.0548 (10)	0.0758 (13)	0.0633 (12)	−0.0026 (9)	−0.0012 (9)	−0.0029 (10)
C18	0.0624 (12)	0.0841 (15)	0.0979 (16)	−0.0089 (11)	0.0168 (11)	0.0110 (13)
C17	0.0652 (12)	0.0777 (15)	0.0868 (15)	0.0094 (11)	−0.0045 (11)	0.0036 (12)
C5	0.0497 (10)	0.0397 (9)	0.0472 (10)	−0.0017 (7)	0.0080 (8)	0.0049 (7)
C2	0.0497 (10)	0.0492 (10)	0.0580 (11)	−0.0017 (8)	0.0049 (8)	0.0099 (8)
N1	0.0462 (8)	0.0562 (9)	0.0601 (9)	−0.0013 (6)	0.0062 (7)	−0.0077 (7)
C4	0.0564 (10)	0.0476 (10)	0.0486 (10)	−0.0012 (8)	0.0065 (8)	−0.0038 (8)
C3	0.0554 (10)	0.0489 (10)	0.0562 (11)	0.0040 (8)	0.0159 (8)	0.0011 (8)
C6	0.0556 (10)	0.0487 (10)	0.0548 (11)	0.0015 (8)	0.0084 (8)	−0.0069 (9)
C7	0.0593 (11)	0.0507 (11)	0.0565 (11)	−0.0054 (8)	0.0019 (9)	−0.0047 (9)
C1	0.0550 (12)	0.0716 (14)	0.0876 (15)	−0.0007 (10)	0.0052 (11)	0.0053 (11)
C14	0.0566 (10)	0.0416 (9)	0.0516 (11)	0.0016 (8)	0.0052 (8)	−0.0036 (8)
N2	0.0534 (9)	0.0632 (10)	0.0714 (11)	0.0016 (7)	0.0046 (8)	0.0081 (8)
C13	0.0640 (11)	0.0527 (11)	0.0532 (11)	0.0016 (9)	0.0059 (9)	0.0043 (9)
C11	0.0556 (11)	0.0541 (11)	0.0653 (12)	−0.0026 (8)	0.0073 (9)	−0.0135 (9)
C15	0.0649 (12)	0.0516 (11)	0.0584 (11)	−0.0029 (9)	0.0098 (9)	0.0045 (9)
C16	0.0658 (12)	0.0564 (11)	0.0576 (11)	0.0019 (9)	−0.0045 (9)	0.0019 (9)
C12	0.0679 (12)	0.0585 (12)	0.0601 (12)	−0.0068 (9)	0.0189 (9)	−0.0022 (10)
C10	0.0660 (13)	0.0821 (15)	0.0966 (17)	−0.0098 (11)	0.0147 (12)	−0.0188 (13)

O1—C1	1.204 (2)	C2—C3	1.389 (2)
O2—C10	1.212 (3)	C2—C1	1.457 (3)
C9—N1	1.448 (2)	C4—C3	1.379 (2)
C9—H9A	0.96	C4—H4	0.93
C9—H9B	0.96	C3—H3	0.93
C9—H9C	0.96	C6—C7	1.375 (2)
C8—N1	1.454 (2)	C6—H6	0.93
C8—H8A	0.96	C7—H7	0.93
C8—H8B	0.96	C1—H1	0.93
C8—H8C	0.96	C14—N2	1.366 (2)
C18—N2	1.450 (2)	C14—C13	1.399 (2)
C18—H18A	0.96	C14—C15	1.409 (2)
C18—H18B	0.96	C13—C12	1.374 (3)
C18—H18C	0.96	C13—H13	0.93
C17—N2	1.451 (2)	C11—C12	1.384 (3)
C17—H17A	0.96	C11—C16	1.389 (3)
C17—H17B	0.96	C11—C10	1.454 (3)
C17—H17C	0.96	C15—C16	1.374 (2)
C5—N1	1.366 (2)	C15—H15	0.93
C5—C4	1.407 (2)	C16—H16	0.93
C5—C6	1.407 (2)	C12—H12	0.93
C2—C7	1.386 (2)	C10—H10	0.93
N1—C9—H9A	109.5	C4—C3—C2	121.02 (16)
N1—C9—H9B	109.5	C4—C3—H3	119.5
H9A—C9—H9B	109.5	C2—C3—H3	119.5
N1—C9—H9C	109.5	C7—C6—C5	120.61 (16)
H9A—C9—H9C	109.5	C7—C6—H6	119.7
H9B—C9—H9C	109.5	C5—C6—H6	119.7
N1—C8—H8A	109.5	C6—C7—C2	121.65 (16)
N1—C8—H8B	109.5	C6—C7—H7	119.2
H8A—C8—H8B	109.5	C2—C7—H7	119.2
N1—C8—H8C	109.5	O1—C1—C2	126.2 (2)
H8A—C8—H8C	109.5	O1—C1—H1	116.9
H8B—C8—H8C	109.5	C2—C1—H1	116.9
N2—C18—H18A	109.5	N2—C14—C13	121.43 (16)
N2—C18—H18B	109.5	N2—C14—C15	121.09 (16)
H18A—C18—H18B	109.5	C13—C14—C15	117.46 (16)
N2—C18—H18C	109.5	C14—N2—C18	120.96 (15)
H18A—C18—H18C	109.5	C14—N2—C17	121.23 (15)
H18B—C18—H18C	109.5	C18—N2—C17	117.37 (15)
N2—C17—H17A	109.5	C12—C13—C14	121.13 (17)
N2—C17—H17B	109.5	C12—C13—H13	119.4
H17A—C17—H17B	109.5	C14—C13—H13	119.4
N2—C17—H17C	109.5	C12—C11—C16	117.64 (17)
H17A—C17—H17C	109.5	C12—C11—C10	122.03 (19)
H17B—C17—H17C	109.5	C16—C11—C10	120.32 (19)
N1—C5—C4	120.93 (15)	C16—C15—C14	120.27 (17)
N1—C5—C6	121.63 (15)	C16—C15—H15	119.9
C4—C5—C6	117.44 (15)	C14—C15—H15	119.9
C7—C2—C3	118.28 (16)	C15—C16—C11	121.97 (17)
C7—C2—C1	120.65 (17)	C15—C16—H16	119.0
C3—C2—C1	121.07 (17)	C11—C16—H16	119.0
C5—N1—C9	121.13 (15)	C13—C12—C11	121.50 (17)
C5—N1—C8	120.89 (14)	C13—C12—H12	119.3
C9—N1—C8	117.86 (14)	C11—C12—H12	119.3
C3—C4—C5	120.99 (16)	O2—C10—C11	125.1 (2)
C3—C4—H4	119.5	O2—C10—H10	117.4
C5—C4—H4	119.5	C11—C10—H10	117.4

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.96	2.57	3.459 (3)	155
C3—H3···Cg1	0.93	2.78	3.593 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.96	2.57	3.459 (3)	155
C3—H3⋯Cg1	0.93	2.78	3.593 (3)	146

Symmetry code: (i) .