o-(2-Bromo­eth­oxy)benzaldehyde

Mol­ecules of the title compound, C₉H₉BrO₂, form a chain, via π–π stacking inter­actions, which runs along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.038
• wR factor = 0.100
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   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
   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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker,1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

o-(2-Bromoethoxy)benzaldehyde

Crystal data

C9H9BrO2	Dx = 1.663 Mg m^−3
Mr = 229.07	Melting point: 51 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.7453 (9) Å	Cell parameters from 3002 reflections
b = 16.2325 (19) Å	θ = 2.7–28.2°
c = 7.3667 (9) Å	µ = 4.45 mm^−1
β = 98.908 (2)°	T = 296 K
V = 915.01 (19) Å^3	Pillar, colorless
Z = 4	0.20 × 0.15 × 0.10 mm
F(000) = 456

Data collection

Bruker SMART APEX-II CCD diffractometer	1697 independent reflections
Radiation source: fine-focus sealed tube	1494 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.470, Tmax = 0.665	k = −19→16
4818 measured reflections	l = −8→8

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0484P)^2 + 0.8593P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
1697 reflections	Δρmax = 0.69 e Å^−3
110 parameters	Δρmin = −0.48 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

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 > 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
Br1	0.05900 (5)	0.65867 (3)	−0.06453 (5)	0.0692 (2)
C2	0.2713 (4)	0.49752 (19)	0.4071 (4)	0.0435 (6)
C1	0.3212 (4)	0.41640 (18)	0.3741 (4)	0.0444 (7)
C7	0.3927 (4)	0.3950 (2)	0.2068 (5)	0.0539 (8)
H7	0.3945	0.4358	0.1185	0.065*
C6	0.3097 (5)	0.3565 (2)	0.5069 (5)	0.0563 (8)
H6	0.3400	0.3023	0.4850	0.068*
C3	0.2187 (4)	0.5175 (2)	0.5727 (4)	0.0512 (7)
H3	0.1890	0.5715	0.5964	0.061*
C5	0.2539 (5)	0.3762 (2)	0.6700 (5)	0.0641 (9)
H5	0.2457	0.3356	0.7572	0.077*
C4	0.2104 (5)	0.4565 (2)	0.7032 (5)	0.0609 (9)
H4	0.1751	0.4701	0.8145	0.073*
O1	0.4493 (4)	0.32785 (15)	0.1762 (4)	0.0743 (8)
O2	0.2786 (3)	0.55232 (13)	0.2680 (3)	0.0533 (6)
C8	0.2426 (4)	0.63677 (18)	0.3007 (5)	0.0487 (7)
H8A	0.3269	0.6580	0.4009	0.058*
H8B	0.1267	0.6424	0.3336	0.058*
C9	0.2543 (5)	0.6835 (2)	0.1281 (5)	0.0540 (8)
H9A	0.3629	0.6697	0.0852	0.065*
H9B	0.2556	0.7421	0.1541	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0732 (3)	0.0767 (3)	0.0574 (3)	−0.00283 (18)	0.00945 (19)	0.01047 (17)
C2	0.0390 (14)	0.0448 (15)	0.0455 (15)	−0.0021 (12)	0.0030 (12)	0.0006 (12)
C1	0.0397 (15)	0.0429 (16)	0.0483 (16)	−0.0012 (12)	−0.0007 (12)	−0.0011 (13)
C7	0.0584 (19)	0.0459 (18)	0.0562 (19)	0.0000 (14)	0.0055 (15)	−0.0056 (14)
C6	0.0510 (18)	0.0477 (18)	0.067 (2)	−0.0030 (14)	0.0002 (16)	0.0067 (15)
C3	0.0514 (17)	0.0539 (19)	0.0484 (17)	0.0010 (14)	0.0086 (14)	−0.0014 (14)
C5	0.062 (2)	0.065 (2)	0.064 (2)	−0.0026 (17)	0.0076 (17)	0.0226 (18)
C4	0.058 (2)	0.076 (2)	0.0489 (19)	0.0010 (17)	0.0104 (15)	0.0069 (16)
O1	0.088 (2)	0.0513 (15)	0.087 (2)	0.0089 (13)	0.0236 (16)	−0.0144 (13)
O2	0.0750 (15)	0.0389 (11)	0.0489 (12)	0.0088 (10)	0.0189 (11)	0.0023 (9)
C8	0.0557 (18)	0.0370 (15)	0.0546 (18)	0.0018 (13)	0.0119 (14)	−0.0043 (13)
C9	0.061 (2)	0.0417 (16)	0.062 (2)	−0.0048 (14)	0.0171 (16)	0.0008 (14)

Geometric parameters (Å, º)

Br1—C9	1.949 (4)	C3—H3	0.9300
C2—O2	1.365 (4)	C5—C4	1.379 (6)
C2—C3	1.383 (4)	C5—H5	0.9300
C2—C1	1.404 (4)	C4—H4	0.9300
C1—C6	1.392 (5)	O2—C8	1.427 (4)
C1—C7	1.469 (4)	C8—C9	1.495 (5)
C7—O1	1.209 (4)	C8—H8A	0.9700
C7—H7	0.9300	C8—H8B	0.9700
C6—C5	1.376 (6)	C9—H9A	0.9700
C6—H6	0.9300	C9—H9B	0.9700
C3—C4	1.388 (5)
O2—C2—C3	124.2 (3)	C4—C5—H5	120.2
O2—C2—C1	115.9 (3)	C5—C4—C3	120.8 (3)
C3—C2—C1	119.9 (3)	C5—C4—H4	119.6
C6—C1—C2	119.0 (3)	C3—C4—H4	119.6
C6—C1—C7	119.9 (3)	C2—O2—C8	117.9 (2)
C2—C1—C7	121.1 (3)	O2—C8—C9	107.8 (3)
O1—C7—C1	124.3 (3)	O2—C8—H8A	110.2
O1—C7—H7	117.8	C9—C8—H8A	110.2
C1—C7—H7	117.8	O2—C8—H8B	110.2
C5—C6—C1	120.9 (3)	C9—C8—H8B	110.2
C5—C6—H6	119.5	H8A—C8—H8B	108.5
C1—C6—H6	119.5	C8—C9—Br1	111.9 (2)
C2—C3—C4	119.7 (3)	C8—C9—H9A	109.2
C2—C3—H3	120.1	Br1—C9—H9A	109.2
C4—C3—H3	120.1	C8—C9—H9B	109.2
C6—C5—C4	119.6 (3)	Br1—C9—H9B	109.2
C6—C5—H5	120.2	H9A—C9—H9B	107.9
O2—C2—C1—C6	−177.2 (3)	C1—C2—C3—C4	−2.0 (5)
C3—C2—C1—C6	2.7 (4)	C1—C6—C5—C4	−0.6 (5)
O2—C2—C1—C7	5.7 (4)	C6—C5—C4—C3	1.3 (6)
C3—C2—C1—C7	−174.4 (3)	C2—C3—C4—C5	0.0 (5)
C6—C1—C7—O1	−2.5 (5)	C3—C2—O2—C8	5.1 (4)
C2—C1—C7—O1	174.6 (3)	C1—C2—O2—C8	−175.1 (3)
C2—C1—C6—C5	−1.4 (5)	C2—O2—C8—C9	−178.6 (3)
C7—C1—C6—C5	175.7 (3)	O2—C8—C9—Br1	71.2 (3)
O2—C2—C3—C4	177.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2	0.93	2.43	2.762 (4)	101
C9—H9A···O1^i	0.97	2.59	3.453 (5)	149

Symmetry code: (i) −x+1, −y+1, −z.