Triclinic polymorph of 4-[4-(4-formyl-phen-oxy)but-oxy]benzaldehyde.

The title compound, C18H18O4, is a triclinic polymorph of the previously reported monoclinic polymorph [Han & Zhen (2005 ▶). Acta Cryst. E61, o4358-o4359]. In the crystal of the triclinic polymorph, molecules are linked by two pairs of C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (102), and enclosing loops with graph set motifs of R2(2)(8) and R2(2)(6).

Related literature

For the monoclinic polymorph, see: Han & Zhen (2005 ▶). For related structures and the synthesis of similar compounds, see: Balić et al. (2012 ▶); Ma & Cao (2011 ▶); Dehno Khalaji et al. (2011 ▶); Narasimha Moorthy et al. (2005 ▶); Ilhan et al. (2007 ▶). For graph-set analysis of hydrogen bonds, see Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H18O4

M = 298.32

Triclinic,

a = 4.4969 (2) Å

b = 7.9507 (6) Å

c = 11.0679 (8) Å

α = 73.854 (6)°

β = 84.788 (5)°

γ = 80.903 (5)°

V = 374.86 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.09 mm−1

T = 190 K

0.59 × 0.35 × 0.21 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.683, T max = 1.000

2235 measured reflections

1473 independent reflections

1272 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.04

1473 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶), PARST97 (Nardelli, 1995 ▶) and Mercury (Macrae et al., 2006 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050994/ng5308sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050994/ng5308Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050994/ng5308Isup3.cml

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

C18H18O4	Z = 1
Mr = 298.32	F(000) = 158
Triclinic, P1	Dx = 1.321 Mg m−3
a = 4.4969 (2) Å	Mo Kα radiation, λ = 0.7107 Å
b = 7.9507 (6) Å	Cell parameters from 1657 reflections
c = 11.0679 (8) Å	θ = 4.6–28.5°
α = 73.854 (6)°	µ = 0.09 mm−1
β = 84.788 (5)°	T = 190 K
γ = 80.903 (5)°	Block, colourless
V = 374.86 (4) Å3	0.59 × 0.35 × 0.21 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1473 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1272 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
Detector resolution: 16.3426 pixels mm-1	θmax = 26.0°, θmin = 4.6°
ω scans	h = −5→4
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→9
Tmin = 0.683, Tmax = 1.000	l = −13→13
2235 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0676P)2 + 0.0807P] where P = (Fo2 + 2Fc2)/3
1473 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. (CrysAlis PRO RED; Oxford Diffraction, 2009)

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	0.2410 (3)	−0.49759 (14)	0.85962 (11)	0.0490 (4)
O2	0.8584 (2)	0.19238 (11)	0.61242 (8)	0.0289 (3)
C1	0.2367 (3)	−0.3608 (2)	0.88964 (14)	0.0377 (4)
H1	0.1248	−0.3496	0.9647	0.045*
C2	0.3920 (3)	−0.21240 (17)	0.81809 (13)	0.0283 (3)
C3	0.3932 (3)	−0.06701 (18)	0.86379 (12)	0.0308 (3)
H3	0.2870	−0.0627	0.9413	0.037*
C4	0.5460 (3)	0.07238 (17)	0.79893 (12)	0.0280 (3)
H4	0.5453	0.1711	0.8315	0.034*
C5	0.7004 (3)	0.06505 (16)	0.68513 (12)	0.0242 (3)
C6	0.6963 (3)	−0.07927 (18)	0.63690 (13)	0.0292 (3)
H6	0.7991	−0.0831	0.5586	0.035*
C7	0.5437 (3)	−0.21533 (17)	0.70273 (13)	0.0305 (3)
H7	0.5410	−0.3130	0.6694	0.037*
C8	0.8898 (3)	0.33927 (16)	0.65981 (12)	0.0268 (3)
H8A	0.9914	0.2970	0.7406	0.032*
H8B	0.6892	0.4045	0.6742	0.032*
C9	1.0762 (3)	0.45809 (17)	0.56216 (12)	0.0276 (3)
H9A	1.2708	0.3883	0.5457	0.033*
H9B	1.1206	0.5532	0.5967	0.033*

	U11	U22	U33	U12	U13	U23
O1	0.0659 (8)	0.0366 (7)	0.0488 (7)	−0.0282 (5)	0.0138 (6)	−0.0119 (5)
O2	0.0378 (5)	0.0208 (5)	0.0297 (5)	−0.0128 (4)	0.0082 (4)	−0.0076 (4)
C1	0.0431 (8)	0.0373 (8)	0.0326 (8)	−0.0182 (6)	0.0064 (6)	−0.0048 (6)
C2	0.0292 (7)	0.0262 (7)	0.0282 (7)	−0.0087 (5)	−0.0004 (5)	−0.0026 (5)
C3	0.0335 (7)	0.0356 (8)	0.0233 (6)	−0.0095 (6)	0.0045 (5)	−0.0072 (6)
C4	0.0337 (7)	0.0255 (7)	0.0271 (7)	−0.0079 (5)	0.0007 (5)	−0.0094 (5)
C5	0.0245 (6)	0.0211 (6)	0.0257 (6)	−0.0057 (5)	0.0005 (5)	−0.0032 (5)
C6	0.0342 (7)	0.0254 (7)	0.0291 (7)	−0.0087 (5)	0.0073 (5)	−0.0095 (6)
C7	0.0352 (7)	0.0235 (7)	0.0346 (7)	−0.0101 (5)	0.0047 (6)	−0.0094 (6)
C8	0.0309 (7)	0.0215 (7)	0.0301 (7)	−0.0083 (5)	−0.0009 (5)	−0.0080 (5)
C9	0.0275 (6)	0.0230 (7)	0.0328 (7)	−0.0086 (5)	−0.0023 (5)	−0.0051 (6)

O1—C1	1.2196 (18)	C5—C6	1.3969 (18)
O2—C5	1.3593 (15)	C6—C7	1.3704 (18)
O2—C8	1.4372 (15)	C6—H6	0.9500
C1—C2	1.4652 (18)	C7—H7	0.9500
C1—H1	0.9500	C8—C9	1.5105 (17)
C2—C3	1.3857 (19)	C8—H8A	0.9900
C2—C7	1.396 (2)	C8—H8B	0.9900
C3—C4	1.3871 (18)	C9—C9i	1.525 (3)
C3—H3	0.9500	C9—H9A	0.9900
C4—C5	1.3933 (18)	C9—H9B	0.9900
C4—H4	0.9500
C5—O2—C8	118.23 (10)	C7—C6—H6	120.1
O1—C1—C2	124.62 (14)	C5—C6—H6	120.1
O1—C1—H1	117.7	C6—C7—C2	120.93 (13)
C2—C1—H1	117.7	C6—C7—H7	119.5
C3—C2—C7	118.64 (12)	C2—C7—H7	119.5
C3—C2—C1	120.77 (13)	O2—C8—C9	107.25 (10)
C7—C2—C1	120.58 (13)	O2—C8—H8A	110.3
C2—C3—C4	121.52 (12)	C9—C8—H8A	110.3
C2—C3—H3	119.2	O2—C8—H8B	110.3
C4—C3—H3	119.2	C9—C8—H8B	110.3
C3—C4—C5	118.82 (12)	H8A—C8—H8B	108.5
C3—C4—H4	120.6	C8—C9—C9i	113.78 (13)
C5—C4—H4	120.6	C8—C9—H9A	108.8
O2—C5—C4	124.74 (12)	C9i—C9—H9A	108.8
O2—C5—C6	115.04 (11)	C8—C9—H9B	108.8
C4—C5—C6	120.22 (12)	C9i—C9—H9B	108.8
C7—C6—C5	119.85 (12)	H9A—C9—H9B	107.7
O1—C1—C2—C3	−175.28 (14)	C3—C4—C5—C6	1.0 (2)
O1—C1—C2—C7	4.3 (2)	O2—C5—C6—C7	179.96 (11)
C7—C2—C3—C4	−1.3 (2)	C4—C5—C6—C7	−1.0 (2)
C1—C2—C3—C4	178.22 (12)	C5—C6—C7—C2	−0.2 (2)
C2—C3—C4—C5	0.2 (2)	C3—C2—C7—C6	1.4 (2)
C8—O2—C5—C4	5.11 (18)	C1—C2—C7—C6	−178.21 (12)
C8—O2—C5—C6	−175.90 (10)	C5—O2—C8—C9	179.31 (10)
C3—C4—C5—O2	179.95 (11)	O2—C8—C9—C9i	64.84 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ii	0.95	2.58	3.4985 (16)	162
C1—H1···O1iii	0.95	2.59	3.3953 (18)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.95	2.58	3.4985 (16)	162
C1—H1⋯O1ii	0.95	2.59	3.3953 (18)	143

Symmetry codes: (i) ; (ii) .