2-(5-Formyl-2-methoxy­phen­oxy)acetonitrile

The title compound, C₁₀H₉NO₃, crystallizes with two mol­ecules in the asymmetric unit. Inter­molecular C—H...O and C—H...(O,O) inter­actions help to consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.130
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C8      ..       5.65 su
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C19     ..       2.98 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   2 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
   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 (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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: SHELXTL.

2-(5-Formyl-2-methoxyphenoxy)acetonitrile

Crystal data

C10H9NO3	Z = 4
Mr = 191.18	F(000) = 400
Triclinic, P1	Dx = 1.331 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.428 (2) Å	Cell parameters from 1562 reflections
b = 10.138 (3) Å	θ = 2.6–26.1°
c = 12.629 (3) Å	µ = 0.10 mm^−1
α = 69.136 (4)°	T = 294 K
β = 84.967 (4)°	Block, colorless
γ = 71.163 (4)°	0.26 × 0.24 × 0.14 mm
V = 953.9 (4) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3322 independent reflections
Radiation source: fine-focus sealed tube	2166 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.958, Tmax = 0.986	k = −12→7
4846 measured reflections	l = −15→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 0.1537P] where P = (Fo^2 + 2Fc^2)/3
3322 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.21 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 > 2σ(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
O1	1.04852 (18)	0.18351 (15)	0.25628 (12)	0.0553 (4)
O2	0.86130 (18)	0.30631 (15)	0.38656 (11)	0.0520 (4)
O3	0.9003 (2)	−0.30154 (18)	0.33447 (15)	0.0757 (5)
O4	0.14123 (18)	0.46534 (15)	1.10577 (11)	0.0555 (4)
O5	0.28560 (18)	0.36657 (15)	0.95150 (11)	0.0522 (4)
O6	0.2227 (3)	0.98548 (19)	0.99402 (16)	0.0892 (6)
N1	1.4131 (3)	−0.0869 (3)	0.2701 (2)	0.0946 (8)
N2	0.3138 (3)	0.4593 (3)	1.3368 (2)	0.1039 (9)
C1	0.9493 (2)	0.1050 (2)	0.32319 (15)	0.0414 (5)
C2	0.9429 (2)	−0.0277 (2)	0.32364 (15)	0.0439 (5)
H2	1.0123	−0.0740	0.2772	0.053*
C3	0.8322 (2)	−0.0938 (2)	0.39386 (16)	0.0437 (5)
C4	0.7324 (3)	−0.0260 (2)	0.46263 (17)	0.0498 (5)
H4	0.6599	−0.0712	0.5102	0.060*
C5	0.7373 (3)	0.1085 (2)	0.46277 (16)	0.0486 (5)
H5	0.6674	0.1542	0.5093	0.058*
C6	0.8458 (2)	0.1747 (2)	0.39403 (15)	0.0416 (5)
C7	0.7596 (3)	0.3815 (2)	0.4572 (2)	0.0641 (6)
H7A	0.6434	0.4053	0.4383	0.096*
H7B	0.7850	0.4713	0.4455	0.096*
H7C	0.7820	0.3183	0.5352	0.096*
C8	0.8215 (3)	−0.2342 (2)	0.39333 (19)	0.0576 (6)
H8	0.7474	−0.2751	0.4427	0.069*
C9	1.1454 (3)	0.1277 (2)	0.17515 (17)	0.0552 (6)
H9A	1.1776	0.2069	0.1172	0.066*
H9B	1.0785	0.0930	0.1389	0.066*
C10	1.2959 (3)	0.0055 (3)	0.2283 (2)	0.0626 (6)
C11	0.2136 (2)	0.5577 (2)	1.02507 (15)	0.0413 (5)
C12	0.2131 (2)	0.6939 (2)	1.02180 (16)	0.0460 (5)
H12	0.1595	0.7313	1.0774	0.055*
C13	0.2931 (3)	0.7770 (2)	0.93486 (16)	0.0456 (5)
C14	0.3736 (3)	0.7200 (2)	0.85452 (16)	0.0485 (5)
H14	0.4292	0.7745	0.7977	0.058*
C15	0.3739 (2)	0.5835 (2)	0.85621 (16)	0.0463 (5)
H15	0.4278	0.5468	0.8003	0.056*
C16	0.2940 (2)	0.5018 (2)	0.94114 (15)	0.0410 (5)
C17	0.3681 (3)	0.3024 (3)	0.86972 (19)	0.0608 (6)
H17A	0.3189	0.3649	0.7958	0.091*
H17B	0.3560	0.2058	0.8882	0.091*
H17C	0.4851	0.2933	0.8701	0.091*
C18	0.2893 (3)	0.9246 (3)	0.9287 (2)	0.0629 (6)
H18	0.3435	0.9759	0.8687	0.075*
C19	0.0745 (3)	0.5062 (3)	1.20008 (17)	0.0540 (6)
H19A	0.0018	0.4482	1.2396	0.065*
H19B	0.0077	0.6103	1.1743	0.065*
C20	0.2076 (3)	0.4816 (3)	1.2773 (2)	0.0669 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0623 (10)	0.0494 (9)	0.0606 (9)	−0.0257 (7)	0.0292 (7)	−0.0256 (7)
O2	0.0655 (10)	0.0448 (8)	0.0527 (8)	−0.0218 (7)	0.0161 (7)	−0.0245 (7)
O3	0.0896 (13)	0.0658 (11)	0.0915 (13)	−0.0331 (9)	0.0272 (10)	−0.0483 (10)
O4	0.0741 (10)	0.0565 (9)	0.0501 (8)	−0.0348 (8)	0.0261 (7)	−0.0278 (7)
O5	0.0624 (9)	0.0507 (9)	0.0533 (9)	−0.0219 (7)	0.0140 (7)	−0.0284 (7)
O6	0.1348 (18)	0.0684 (12)	0.0850 (13)	−0.0476 (12)	0.0337 (12)	−0.0436 (10)
N1	0.0684 (16)	0.117 (2)	0.0784 (16)	−0.0035 (15)	0.0156 (13)	−0.0368 (15)
N2	0.0786 (18)	0.166 (3)	0.0658 (15)	−0.0277 (17)	0.0108 (13)	−0.0495 (16)
C1	0.0423 (11)	0.0412 (11)	0.0388 (11)	−0.0130 (9)	0.0058 (9)	−0.0129 (9)
C2	0.0455 (12)	0.0432 (12)	0.0414 (11)	−0.0091 (9)	0.0055 (9)	−0.0180 (9)
C3	0.0468 (12)	0.0395 (11)	0.0451 (11)	−0.0137 (9)	0.0035 (9)	−0.0154 (9)
C4	0.0519 (13)	0.0528 (13)	0.0485 (12)	−0.0237 (10)	0.0146 (10)	−0.0187 (10)
C5	0.0500 (12)	0.0515 (13)	0.0451 (12)	−0.0135 (10)	0.0122 (10)	−0.0226 (10)
C6	0.0452 (12)	0.0408 (12)	0.0376 (11)	−0.0121 (9)	0.0023 (9)	−0.0138 (9)
C7	0.0816 (17)	0.0539 (14)	0.0667 (15)	−0.0215 (12)	0.0199 (13)	−0.0362 (12)
C8	0.0625 (15)	0.0551 (14)	0.0605 (14)	−0.0248 (11)	0.0098 (12)	−0.0227 (12)
C9	0.0620 (14)	0.0539 (14)	0.0495 (12)	−0.0206 (11)	0.0230 (11)	−0.0203 (11)
C10	0.0586 (16)	0.0777 (18)	0.0545 (14)	−0.0210 (14)	0.0240 (12)	−0.0318 (13)
C11	0.0435 (11)	0.0446 (12)	0.0387 (11)	−0.0179 (9)	0.0061 (9)	−0.0154 (9)
C12	0.0503 (12)	0.0519 (13)	0.0392 (11)	−0.0153 (10)	0.0060 (9)	−0.0214 (10)
C13	0.0515 (12)	0.0445 (12)	0.0396 (11)	−0.0169 (10)	0.0017 (9)	−0.0115 (9)
C14	0.0528 (13)	0.0527 (13)	0.0384 (11)	−0.0220 (10)	0.0068 (9)	−0.0101 (10)
C15	0.0455 (12)	0.0545 (13)	0.0394 (11)	−0.0136 (10)	0.0059 (9)	−0.0198 (10)
C16	0.0397 (11)	0.0459 (12)	0.0383 (11)	−0.0126 (9)	0.0016 (9)	−0.0165 (9)
C17	0.0675 (15)	0.0612 (15)	0.0659 (15)	−0.0187 (12)	0.0131 (12)	−0.0401 (12)
C18	0.0800 (17)	0.0567 (15)	0.0572 (14)	−0.0319 (13)	0.0072 (12)	−0.0178 (12)
C19	0.0592 (14)	0.0639 (14)	0.0483 (12)	−0.0278 (11)	0.0220 (11)	−0.0274 (11)
C20	0.0665 (17)	0.0882 (19)	0.0468 (14)	−0.0235 (14)	0.0210 (13)	−0.0297 (13)

Geometric parameters (Å, º)

O1—C1	1.369 (2)	C7—H7B	0.9600
O1—C9	1.416 (2)	C7—H7C	0.9600
O2—C6	1.351 (2)	C8—H8	0.9300
O2—C7	1.428 (2)	C9—C10	1.461 (3)
O3—C8	1.200 (2)	C9—H9A	0.9700
O4—C11	1.366 (2)	C9—H9B	0.9700
O4—C19	1.411 (2)	C11—C12	1.365 (3)
O5—C16	1.355 (2)	C11—C16	1.399 (3)
O5—C17	1.426 (2)	C12—C13	1.396 (3)
O6—C18	1.198 (3)	C12—H12	0.9300
N1—C10	1.129 (3)	C13—C14	1.367 (3)
N2—C20	1.133 (3)	C13—C18	1.460 (3)
C1—C2	1.361 (3)	C14—C15	1.375 (3)
C1—C6	1.406 (3)	C14—H14	0.9300
C2—C3	1.394 (3)	C15—C16	1.375 (3)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.363 (3)	C17—H17A	0.9600
C3—C8	1.458 (3)	C17—H17B	0.9600
C4—C5	1.378 (3)	C17—H17C	0.9600
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.372 (3)	C19—C20	1.453 (4)
C5—H5	0.9300	C19—H19A	0.9700
C7—H7A	0.9600	C19—H19B	0.9700
C1—O1—C9	117.65 (16)	H9A—C9—H9B	108.0
C6—O2—C7	117.76 (16)	N1—C10—C9	178.6 (3)
C11—O4—C19	117.71 (15)	C12—C11—O4	125.63 (17)
C16—O5—C17	117.86 (15)	C12—C11—C16	119.96 (18)
C2—C1—O1	125.67 (17)	O4—C11—C16	114.42 (17)
C2—C1—C6	120.26 (17)	C11—C12—C13	119.94 (18)
O1—C1—C6	114.06 (17)	C11—C12—H12	120.0
C1—C2—C3	119.79 (18)	C13—C12—H12	120.0
C1—C2—H2	120.1	C14—C13—C12	119.51 (19)
C3—C2—H2	120.1	C14—C13—C18	120.05 (19)
C4—C3—C2	119.76 (18)	C12—C13—C18	120.43 (19)
C4—C3—C8	119.89 (18)	C13—C14—C15	121.17 (19)
C2—C3—C8	120.34 (18)	C13—C14—H14	119.4
C3—C4—C5	121.00 (18)	C15—C14—H14	119.4
C3—C4—H4	119.5	C14—C15—C16	119.52 (19)
C5—C4—H4	119.5	C14—C15—H15	120.2
C6—C5—C4	119.81 (19)	C16—C15—H15	120.2
C6—C5—H5	120.1	O5—C16—C15	124.84 (17)
C4—C5—H5	120.1	O5—C16—C11	115.28 (16)
O2—C6—C5	125.13 (17)	C15—C16—C11	119.88 (19)
O2—C6—C1	115.50 (16)	O5—C17—H17A	109.5
C5—C6—C1	119.36 (19)	O5—C17—H17B	109.5
O2—C7—H7A	109.5	H17A—C17—H17B	109.5
O2—C7—H7B	109.5	O5—C17—H17C	109.5
H7A—C7—H7B	109.5	H17A—C17—H17C	109.5
O2—C7—H7C	109.5	H17B—C17—H17C	109.5
H7A—C7—H7C	109.5	O6—C18—C13	125.8 (2)
H7B—C7—H7C	109.5	O6—C18—H18	117.1
O3—C8—C3	125.5 (2)	C13—C18—H18	117.1
O3—C8—H8	117.3	O4—C19—C20	110.88 (18)
C3—C8—H8	117.3	O4—C19—H19A	109.5
O1—C9—C10	110.99 (17)	C20—C19—H19A	109.5
O1—C9—H9A	109.4	O4—C19—H19B	109.5
C10—C9—H9A	109.4	C20—C19—H19B	109.5
O1—C9—H9B	109.4	H19A—C19—H19B	108.1
C10—C9—H9B	109.4	N2—C20—C19	178.2 (3)
C9—O1—C1—C2	4.3 (3)	C19—O4—C11—C12	−6.7 (3)
C9—O1—C1—C6	−174.45 (17)	C19—O4—C11—C16	172.93 (17)
O1—C1—C2—C3	−178.07 (18)	O4—C11—C12—C13	179.46 (18)
C6—C1—C2—C3	0.6 (3)	C16—C11—C12—C13	−0.1 (3)
C1—C2—C3—C4	−0.8 (3)	C11—C12—C13—C14	−1.0 (3)
C1—C2—C3—C8	178.65 (18)	C11—C12—C13—C18	178.25 (18)
C2—C3—C4—C5	1.0 (3)	C12—C13—C14—C15	1.6 (3)
C8—C3—C4—C5	−178.49 (19)	C18—C13—C14—C15	−177.69 (19)
C3—C4—C5—C6	−1.0 (3)	C13—C14—C15—C16	−1.0 (3)
C7—O2—C6—C5	1.3 (3)	C17—O5—C16—C15	1.2 (3)
C7—O2—C6—C1	−179.69 (17)	C17—O5—C16—C11	−178.76 (17)
C4—C5—C6—O2	179.70 (18)	C14—C15—C16—O5	179.88 (17)
C4—C5—C6—C1	0.8 (3)	C14—C15—C16—C11	−0.2 (3)
C2—C1—C6—O2	−179.65 (16)	C12—C11—C16—O5	−179.33 (16)
O1—C1—C6—O2	−0.8 (2)	O4—C11—C16—O5	1.0 (2)
C2—C1—C6—C5	−0.6 (3)	C12—C11—C16—C15	0.7 (3)
O1—C1—C6—C5	178.22 (17)	O4—C11—C16—C15	−178.93 (17)
C4—C3—C8—O3	178.2 (2)	C14—C13—C18—O6	179.9 (2)
C2—C3—C8—O3	−1.3 (3)	C12—C13—C18—O6	0.7 (4)
C1—O1—C9—C10	−79.0 (2)	C11—O4—C19—C20	−74.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O2^i	0.97	2.39	3.330 (2)	162
C19—H19A···O1^i	0.97	2.52	3.168 (3)	125
C9—H9A···O5^ii	0.97	2.46	3.410 (2)	168
C9—H9A···O4^ii	0.97	2.49	3.206 (3)	131
C19—H19B···O3^iii	0.97	2.48	2.985 (3)	112
C9—H9B···O6^iv	0.97	2.49	3.036 (3)	116

Symmetry codes: (i) x−1, y, z+1; (ii) x+1, y, z−1; (iii) x−1, y+1, z+1; (iv) x+1, y−1, z−1.