2-Chloro-3-hydroxy-4-methoxy­benz­aldehyde

The molecule of the title compound, C₈H₇ClO₃, is almost planar, and there are intramolecular O—H...O, C—H...O and C—H...Cl interactions. The mol­ecules are connected by O—H...O and C—H...O interactions, forming two-dimensional networks.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.098
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl     ..  Cl       =       3.28 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 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

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C8H7ClO3	F(000) = 384
Mr = 186.59	Dx = 1.590 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7841 reflections
a = 6.4910 (5) Å	θ = 3.5–27.3°
b = 14.2605 (13) Å	µ = 0.45 mm^−1
c = 8.5148 (9) Å	T = 293 K
β = 98.457 (3)°	Prism, colorless
V = 779.60 (12) Å^3	0.26 × 0.22 × 0.18 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	1391 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.026
ω scans	θmax = 27.3°, θmin = 2.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
Tmin = 0.888, Tmax = 0.923	k = −18→18
3309 measured reflections	l = −10→10
1755 independent reflections

Refinement

Refinement on F^2	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.1956P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.036	(Δ/σ)max < 0.001
wR(F^2) = 0.098	Δρmax = 0.28 e Å^−3
S = 1.01	Δρmin = −0.23 e Å^−3
1755 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
138 parameters	Extinction coefficient: 0.0081 (19)
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl	0.45643 (8)	0.09990 (3)	0.08475 (6)	0.04703 (18)
O1	0.0221 (2)	0.35347 (8)	0.27022 (16)	0.0426 (3)
O2	0.1146 (2)	0.17317 (9)	0.22546 (18)	0.0458 (4)
O3	0.8072 (2)	0.32254 (10)	−0.09200 (17)	0.0508 (4)
C1	0.5252 (3)	0.28639 (12)	0.0432 (2)	0.0333 (4)
C2	0.4010 (3)	0.21799 (11)	0.10152 (19)	0.0315 (4)
C3	0.2322 (3)	0.24144 (11)	0.17545 (19)	0.0323 (4)
C4	0.1883 (3)	0.33706 (11)	0.1944 (2)	0.0331 (4)
C5	0.3100 (3)	0.40532 (12)	0.1387 (2)	0.0408 (4)
C6	0.4749 (3)	0.37954 (13)	0.0640 (2)	0.0408 (4)
C7	0.7016 (3)	0.26397 (14)	−0.0393 (2)	0.0418 (4)
C8	−0.0375 (4)	0.44944 (16)	0.2855 (3)	0.0542 (6)
H2	0.036 (5)	0.1932 (19)	0.277 (3)	0.077 (9)*
H5	0.276 (3)	0.4717 (15)	0.153 (2)	0.052 (6)*
H6	0.551 (3)	0.4274 (14)	0.028 (2)	0.043 (5)*
H7	0.737 (4)	0.2011 (17)	−0.058 (3)	0.063 (7)*
H8A	−0.067 (5)	0.4799 (19)	0.182 (3)	0.082 (9)*
H8B	−0.162 (4)	0.4465 (17)	0.336 (3)	0.063 (7)*
H8C	0.066 (4)	0.4835 (18)	0.349 (3)	0.074 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0513 (3)	0.0316 (2)	0.0625 (3)	0.00517 (19)	0.0229 (2)	−0.00370 (19)
C1	0.0299 (8)	0.0374 (9)	0.0341 (9)	0.0003 (7)	0.0098 (7)	0.0002 (7)
C2	0.0329 (9)	0.0294 (8)	0.0334 (8)	0.0018 (6)	0.0088 (7)	−0.0021 (6)
C3	0.0334 (9)	0.0311 (8)	0.0341 (8)	−0.0014 (6)	0.0105 (7)	−0.0011 (6)
C4	0.0321 (8)	0.0344 (8)	0.0345 (9)	0.0020 (7)	0.0107 (7)	−0.0031 (7)
C5	0.0444 (10)	0.0300 (9)	0.0510 (11)	0.0002 (8)	0.0172 (8)	−0.0023 (7)
C6	0.0407 (10)	0.0349 (9)	0.0504 (11)	−0.0044 (8)	0.0186 (8)	0.0026 (7)
C7	0.0376 (10)	0.0454 (10)	0.0454 (10)	0.0011 (8)	0.0160 (8)	−0.0022 (8)
C8	0.0498 (12)	0.0439 (11)	0.0735 (16)	0.0095 (10)	0.0243 (12)	−0.0115 (11)
O1	0.0406 (7)	0.0394 (7)	0.0528 (8)	0.0053 (6)	0.0238 (6)	−0.0027 (6)
O2	0.0463 (8)	0.0346 (7)	0.0634 (9)	−0.0036 (6)	0.0313 (7)	−0.0014 (6)
O3	0.0414 (8)	0.0579 (8)	0.0584 (9)	−0.0033 (6)	0.0255 (6)	0.0010 (7)

Geometric parameters (Å, º)

Cl—C2	1.7322 (16)	C7—H7	0.94 (2)
C1—C7	1.464 (2)	C8—H8A	0.98 (3)
C2—C3	1.383 (2)	C8—H8B	0.97 (3)
C2—C1	1.402 (2)	C8—H8C	0.93 (3)
C3—C4	1.407 (2)	C8—O1	1.433 (2)
C4—C5	1.381 (2)	O1—C4	1.357 (2)
C5—H5	0.98 (2)	O2—C3	1.344 (2)
C6—C5	1.373 (2)	O2—H2	0.77 (3)
C6—C1	1.385 (2)	O3—C7	1.208 (2)
C6—H6	0.92 (2)
C1—C2—Cl	120.67 (13)	C6—C1—C7	119.09 (16)
C1—C6—H6	121.3 (13)	C6—C5—H5	121.1 (13)
C1—C7—H7	121.0 (15)	O1—C4—C5	125.24 (15)
C2—C1—C7	123.30 (16)	O1—C4—C3	114.20 (14)
C2—C3—C4	118.27 (15)	O1—C8—H8C	111.6 (16)
C3—C2—C1	121.90 (15)	O1—C8—H8A	111.2 (16)
C3—C2—Cl	117.42 (13)	O1—C8—H8B	104.6 (15)
C3—O2—H2	111 (2)	O2—C3—C2	119.60 (15)
C4—C5—H5	119.2 (13)	O2—C3—C4	122.13 (15)
C4—O1—C8	116.88 (15)	O3—C7—C1	123.63 (18)
C5—C4—C3	120.55 (15)	O3—C7—H7	115.3 (15)
C5—C6—C1	122.01 (16)	H8A—C8—H8B	111 (2)
C5—C6—H6	116.7 (13)	H8A—C8—H8C	109 (2)
C6—C1—C2	117.61 (15)	H8B—C8—H8C	110 (2)
C6—C5—C4	119.64 (16)
Cl—C2—C1—C6	−178.51 (14)	C2—C3—C4—C5	0.7 (3)
Cl—C2—C1—C7	2.3 (2)	C2—C3—C4—O1	−179.03 (15)
Cl—C2—C3—C4	178.16 (13)	C3—C2—C1—C6	0.9 (3)
Cl—C2—C3—O2	−2.4 (2)	C3—C2—C1—C7	−178.31 (17)
O1—C4—C5—C6	179.83 (18)	C3—C4—C5—C6	0.1 (3)
O2—C3—C4—O1	1.5 (3)	C5—C6—C1—C2	0.0 (3)
O2—C3—C4—C5	−178.67 (17)	C5—C6—C1—C7	179.21 (18)
C1—C2—C3—O2	178.21 (16)	C6—C1—C7—O3	−0.4 (3)
C1—C2—C3—C4	−1.2 (3)	C8—O1—C4—C5	3.5 (3)
C1—C6—C5—C4	−0.5 (3)	C8—O1—C4—C3	−176.69 (18)
C2—C1—C7—O3	178.81 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.77 (3)	2.29 (3)	2.6802 (18)	113 (2)
O2—H2···O3^i	0.77 (3)	2.00 (3)	2.7044 (18)	152 (3)
C6—H6···O3	0.92 (2)	2.56 (2)	2.814 (2)	96.4 (14)
C7—H7···Cl	0.94 (2)	2.74 (2)	3.101 (2)	103.3 (17)
C7—H7···O1^ii	0.94 (2)	2.64 (2)	3.280 (2)	125.6 (18)
C8—H8A···O2^iii	0.98 (3)	2.90 (3)	3.229 (3)	101.0 (17)

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