N-(4-Butyl­phenyl)­salicyl­ald­imine at 160 K

In the title compound, C₁₇H₁₉NO, which is a Schiff base, an intramolecular O—H...N hydrogen bond involving the hydroxy group forms a six-membered ring with a graph-set motif of S(6). Several intermolecular C—H...π interactions occur between adjacent mol­ecules which are arranged perpendicular to one another.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.112
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               1917
           Count of symmetry unique reflns         1923
           Completeness (_total/calc)             99.69%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

N-(4-Butylphenyl)salicylaldimine

Crystal data

C17H19NO	Dx = 1.189 Mg m^−3
Mr = 253.33	Melting point: 311 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1931 reflections
a = 5.5848 (1) Å	θ = 2.0–27.5°
b = 8.0987 (2) Å	µ = 0.07 mm^−1
c = 31.2943 (6) Å	T = 160 K
V = 1415.43 (5) Å^3	Prism, colourless
Z = 4	0.25 × 0.23 × 0.18 mm
F(000) = 544

Data collection

Nonius KappaCCD diffractometer	1474 reflections with I > 2σ(I)
Radiation source: Nonius FR591 sealed tube generator	Rint = 0.058
Horizontally mounted graphite crystal monochromator	θmax = 27.5°, θmin = 2.6°
Detector resolution: 9 pixels mm^-1	h = −7→7
φ and ω scans with κ offsets	k = −8→10
18762 measured reflections	l = −40→40
1917 independent reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0691P)^2] where P = (Fo^2 + 2Fc^2)/3
1917 reflections	(Δ/σ)max = 0.001
177 parameters	Δρmax = 0.16 e Å^−3
1 restraint	Δρmin = −0.13 e Å^−3

Special details

Experimental. Solvent used: ethanol Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.767 (1) Frames collected: 1388 Seconds exposure per frame: 30 Degrees rotation per frame: 0.5 Crystal-Detector distance (mm): 47.0

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
C1	0.6563 (3)	0.1739 (2)	0.81104 (5)	0.0374 (4)
C2	0.4466 (3)	0.0781 (2)	0.81200 (6)	0.0406 (5)
O2	0.3714 (3)	−0.00536 (17)	0.77711 (4)	0.0523 (4)
H2	0.469 (4)	0.014 (3)	0.7547 (6)	0.076 (7)*
C3	0.3120 (4)	0.0683 (2)	0.84937 (6)	0.0457 (5)
H3	0.1698	0.0040	0.8500	0.055*
C4	0.3849 (4)	0.1519 (2)	0.88543 (6)	0.0471 (5)
H4	0.2928	0.1440	0.9109	0.057*
C5	0.5914 (4)	0.2474 (3)	0.88508 (6)	0.0469 (5)
H5	0.6404	0.3048	0.9101	0.056*
C6	0.7244 (4)	0.2581 (2)	0.84803 (5)	0.0438 (5)
H6	0.8651	0.3240	0.8477	0.053*
C7	0.7988 (3)	0.1899 (2)	0.77251 (5)	0.0388 (4)
H7	0.9331	0.2619	0.7725	0.047*
N8	0.7479 (3)	0.10898 (19)	0.73838 (5)	0.0396 (4)
C9	0.8772 (3)	0.1325 (2)	0.69986 (6)	0.0380 (4)
C10	1.0970 (3)	0.2135 (2)	0.69660 (6)	0.0428 (5)
H10	1.1744	0.2535	0.7216	0.051*
C11	1.2021 (4)	0.2354 (2)	0.65683 (5)	0.0441 (5)
H11	1.3516	0.2908	0.6550	0.053*
C12	1.0947 (3)	0.1785 (2)	0.61965 (6)	0.0421 (5)
C13	0.8793 (3)	0.0942 (2)	0.62330 (6)	0.0450 (5)
H13	0.8037	0.0521	0.5984	0.054*
C14	0.7727 (3)	0.0707 (2)	0.66295 (6)	0.0421 (5)
H14	0.6263	0.0115	0.6648	0.050*
C15	1.2052 (4)	0.2143 (2)	0.57678 (5)	0.0501 (5)
H151	1.1660	0.1235	0.5568	0.060*
H152	1.3815	0.2189	0.5798	0.060*
C16	1.1156 (4)	0.3775 (2)	0.55820 (5)	0.0471 (5)
H161	0.9408	0.3691	0.5534	0.057*
H162	1.1426	0.4661	0.5795	0.057*
C17	1.2355 (4)	0.4261 (3)	0.51658 (6)	0.0597 (6)
H171	1.2162	0.3354	0.4956	0.072*
H172	1.4090	0.4416	0.5216	0.072*
C18	1.1318 (6)	0.5838 (3)	0.49793 (6)	0.0752 (8)
H181	0.9611	0.5679	0.4920	0.113*
H182	1.2156	0.6109	0.4713	0.113*
H183	1.1520	0.6742	0.5184	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0371 (10)	0.0351 (9)	0.0402 (9)	0.0019 (9)	−0.0015 (8)	0.0040 (8)
C2	0.0400 (11)	0.0384 (10)	0.0433 (10)	−0.0014 (9)	−0.0012 (9)	0.0007 (9)
O2	0.0503 (9)	0.0572 (9)	0.0494 (9)	−0.0155 (8)	0.0031 (7)	−0.0073 (7)
C3	0.0407 (10)	0.0449 (11)	0.0516 (11)	−0.0029 (10)	0.0044 (9)	0.0034 (9)
C4	0.0501 (12)	0.0457 (11)	0.0456 (11)	0.0054 (11)	0.0086 (10)	0.0049 (9)
C5	0.0508 (12)	0.0485 (11)	0.0415 (10)	0.0014 (11)	−0.0043 (9)	−0.0009 (9)
C6	0.0420 (11)	0.0423 (10)	0.0472 (10)	−0.0017 (10)	−0.0021 (9)	0.0031 (8)
C7	0.0358 (10)	0.0347 (9)	0.0458 (10)	−0.0001 (9)	−0.0011 (8)	0.0026 (8)
N8	0.0381 (9)	0.0380 (8)	0.0426 (8)	0.0002 (8)	0.0009 (7)	0.0010 (7)
C9	0.0369 (10)	0.0334 (9)	0.0436 (9)	0.0038 (9)	0.0006 (8)	−0.0001 (8)
C10	0.0382 (11)	0.0440 (10)	0.0461 (10)	−0.0028 (10)	−0.0024 (8)	−0.0022 (9)
C11	0.0377 (10)	0.0443 (11)	0.0502 (10)	−0.0012 (10)	0.0031 (9)	0.0008 (9)
C12	0.0404 (10)	0.0412 (10)	0.0446 (10)	0.0102 (10)	0.0028 (9)	−0.0013 (8)
C13	0.0399 (11)	0.0511 (12)	0.0438 (10)	0.0046 (11)	−0.0038 (9)	−0.0055 (9)
C14	0.0347 (10)	0.0431 (11)	0.0484 (10)	−0.0006 (10)	−0.0015 (8)	−0.0045 (9)
C15	0.0474 (12)	0.0573 (12)	0.0457 (10)	0.0098 (11)	0.0066 (9)	−0.0012 (9)
C16	0.0503 (12)	0.0483 (11)	0.0428 (10)	0.0017 (11)	0.0031 (9)	−0.0030 (8)
C17	0.0684 (16)	0.0656 (14)	0.0452 (11)	−0.0037 (14)	0.0036 (10)	0.0028 (10)
C18	0.110 (2)	0.0649 (15)	0.0507 (13)	−0.0112 (17)	−0.0040 (13)	0.0087 (11)

Geometric parameters (Å, º)

C1—C6	1.396 (2)	C11—C12	1.388 (2)
C1—C2	1.405 (2)	C11—H11	0.95
C1—C7	1.451 (2)	C12—C13	1.388 (3)
C2—O2	1.351 (2)	C12—C15	1.505 (2)
C2—C3	1.393 (2)	C13—C14	1.389 (2)
O2—H2	0.903 (16)	C13—H13	0.95
C3—C4	1.377 (3)	C14—H14	0.95
C3—H3	0.95	C15—C16	1.528 (3)
C4—C5	1.389 (3)	C15—H151	0.99
C4—H4	0.95	C15—H152	0.99
C5—C6	1.380 (3)	C16—C17	1.517 (2)
C5—H5	0.95	C16—H161	0.99
C6—H6	0.95	C16—H162	0.99
C7—N8	1.285 (2)	C17—C18	1.519 (3)
C7—H7	0.95	C17—H171	0.99
N8—C9	1.418 (2)	C17—H172	0.99
C9—C14	1.387 (2)	C18—H181	0.98
C9—C10	1.395 (3)	C18—H182	0.98
C10—C11	1.387 (2)	C18—H183	0.98
C10—H10	0.95
C6—C1—C2	118.61 (16)	C11—C12—C15	120.43 (18)
C6—C1—C7	119.76 (16)	C13—C12—C15	121.56 (17)
C2—C1—C7	121.61 (15)	C12—C13—C14	120.79 (17)
O2—C2—C3	118.82 (16)	C12—C13—H13	119.6
O2—C2—C1	121.21 (16)	C14—C13—H13	119.6
C3—C2—C1	119.97 (16)	C9—C14—C13	120.95 (16)
C2—O2—H2	110.6 (16)	C9—C14—H14	119.5
C4—C3—C2	120.02 (18)	C13—C14—H14	119.5
C4—C3—H3	120.0	C12—C15—C16	111.82 (15)
C2—C3—H3	120.0	C12—C15—H151	109.3
C3—C4—C5	120.85 (17)	C16—C15—H151	109.3
C3—C4—H4	119.6	C12—C15—H152	109.3
C5—C4—H4	119.6	C16—C15—H152	109.3
C6—C5—C4	119.24 (17)	H151—C15—H152	107.9
C6—C5—H5	120.4	C17—C16—C15	113.99 (17)
C4—C5—H5	120.4	C17—C16—H161	108.8
C5—C6—C1	121.30 (18)	C15—C16—H161	108.8
C5—C6—H6	119.4	C17—C16—H162	108.8
C1—C6—H6	119.4	C15—C16—H162	108.8
N8—C7—C1	121.62 (17)	H161—C16—H162	107.7
N8—C7—H7	119.2	C16—C17—C18	112.3 (2)
C1—C7—H7	119.2	C16—C17—H171	109.1
C7—N8—C9	121.71 (16)	C18—C17—H171	109.1
C14—C9—C10	118.58 (16)	C16—C17—H172	109.1
C14—C9—N8	116.45 (15)	C18—C17—H172	109.1
C10—C9—N8	124.96 (16)	H171—C17—H172	107.9
C11—C10—C9	119.87 (17)	C17—C18—H181	109.5
C11—C10—H10	120.1	C17—C18—H182	109.5
C9—C10—H10	120.1	H181—C18—H182	109.5
C10—C11—C12	121.78 (18)	C17—C18—H183	109.5
C10—C11—H11	119.1	H181—C18—H183	109.5
C12—C11—H11	119.1	H182—C18—H183	109.5
C11—C12—C13	117.97 (17)
C6—C1—C2—O2	179.68 (18)	C7—N8—C9—C10	14.6 (3)
C7—C1—C2—O2	1.1 (2)	C14—C9—C10—C11	2.1 (3)
C6—C1—C2—C3	−0.2 (3)	N8—C9—C10—C11	−177.19 (17)
C7—C1—C2—C3	−178.77 (17)	C9—C10—C11—C12	−0.1 (3)
O2—C2—C3—C4	179.83 (17)	C10—C11—C12—C13	−1.6 (3)
C1—C2—C3—C4	−0.3 (3)	C10—C11—C12—C15	175.86 (18)
C2—C3—C4—C5	0.4 (3)	C11—C12—C13—C14	1.3 (3)
C3—C4—C5—C6	−0.1 (3)	C15—C12—C13—C14	−176.18 (17)
C4—C5—C6—C1	−0.4 (3)	C10—C9—C14—C13	−2.5 (3)
C2—C1—C6—C5	0.6 (3)	N8—C9—C14—C13	176.89 (16)
C7—C1—C6—C5	179.16 (17)	C12—C13—C14—C9	0.8 (3)
C6—C1—C7—N8	177.01 (18)	C11—C12—C15—C16	−89.0 (2)
C2—C1—C7—N8	−4.4 (3)	C13—C12—C15—C16	88.4 (2)
C1—C7—N8—C9	175.77 (15)	C12—C15—C16—C17	175.56 (17)
C7—N8—C9—C14	−164.77 (17)	C15—C16—C17—C18	176.81 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N8	0.90 (2)	1.81 (2)	2.598 (2)	144 (2)
C11—H11···Cg1^i	0.95	3.10	3.7998 (19)	132
C14—H14···Cg1^ii	0.95	2.97	3.7003 (18)	135
C3—H3···Cg2^ii	0.95	2.98	3.7585 (19)	140
C6—H6···Cg2^i	0.95	2.81	3.5976 (19)	141

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2.