Methyl 2-hy­droxy-4-iodo­benzoate

The structure of the title compound, C₈H₇IO₃, at 90 K has monoclinic (P2₁/c) symmetry. The extended structure is layered and displays inter­molecular and intra­molecular hydrogen bonding arising from the same OH group.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.030
• wR factor = 0.057
• Data-to-parameter ratio = 32.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O2       ..O2       .       2.73 Ang.
                                                2-x,1-y,2-z  =      3_767 Check

Alert level C
PLAT354_ALERT_3_C Short  O-H (X0.82,N0.98A)  O3       - H3       .       0.70 Ang.
PLAT411_ALERT_2_C Short Inter H...H Contact  H4       ..H4       .       2.08 Ang.
                                                 -x,1-y,1-z  =      3_566 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.353 Check
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  1.79Ang From I1             -1.99 eA-3
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  1.01Ang From O1      .      -0.47 eA-3

Alert level G
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.80 mm
PLAT795_ALERT_4_G C-Atom in CIF Coordinate List Out-of-Sequence ..         C1 Note
PLAT796_ALERT_4_G O-Atom in CIF Coordinate List Out-of-Sequence ..         O1 Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
                0  2  0,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        122 Note
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       1.51 Note
              Predicted wR2: Based on SigI   2  3.81 or SHELX Weight  5.25       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Methyl 2-hydroxy-4-iodobenzoate

Crystal data

C8H7IO3	F(000) = 528
Mr = 278.04	Dx = 2.156 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.3286 (8) Å	Cell parameters from 6811 reflections
b = 21.334 (4) Å	θ = 2.9–34.1°
c = 9.2941 (16) Å	µ = 3.70 mm^−1
β = 93.744 (4)°	T = 90 K
V = 856.4 (3) Å^3	Plate, pale yellow
Z = 4	0.80 × 0.20 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer	3315 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.049
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 35.1°, θmin = 2.4°
Tmin = 0.564, Tmax = 0.747	h = −6→6
23320 measured reflections	k = −33→34
3651 independent reflections	l = −14→15

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.057	w = 1/[σ^2(Fo^2) + 1.660P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.001
3651 reflections	Δρmax = 1.27 e Å^−3
114 parameters	Δρmin = −1.92 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The O-bound H atom was located in a difference map and its position was freely refined. The C-bound H atoms were geometrically placed (C—H = 0.95–0.98 Å) and refined as riding atoms.

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

	x	y	z	Uiso*/Ueq
I1	0.05964 (3)	0.25795 (2)	0.54095 (2)	0.01430 (4)
O3	0.7859 (4)	0.39459 (9)	0.91310 (18)	0.0170 (3)
O1	0.4603 (4)	0.56516 (8)	0.72915 (18)	0.0180 (3)
O2	0.7790 (4)	0.51960 (9)	0.89865 (19)	0.0212 (4)
C6	0.2313 (5)	0.34266 (10)	0.6295 (2)	0.0127 (4)
C7	0.4516 (5)	0.34172 (10)	0.7453 (2)	0.0128 (4)
H7	0.522507	0.302965	0.785568	0.015*
C8	0.5675 (5)	0.39821 (10)	0.8018 (2)	0.0121 (3)
C1	0.5827 (6)	0.62513 (11)	0.7783 (3)	0.0203 (5)
H1A	0.499780	0.658300	0.713823	0.030*
H1B	0.809060	0.624553	0.777897	0.030*
H1C	0.522278	0.633151	0.876394	0.030*
C5	0.1189 (5)	0.39860 (11)	0.5688 (2)	0.0161 (4)
H5	−0.033554	0.398522	0.490504	0.019*
C3	0.4577 (5)	0.45534 (10)	0.7425 (2)	0.0123 (4)
C2	0.5823 (5)	0.51534 (11)	0.7990 (2)	0.0144 (4)
C4	0.2359 (5)	0.45406 (10)	0.6259 (2)	0.0156 (4)
H4	0.163744	0.492573	0.584857	0.019*
H3	0.836 (8)	0.4252 (17)	0.929 (4)	0.025 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01408 (6)	0.01099 (7)	0.01764 (7)	−0.00031 (5)	−0.00056 (4)	−0.00134 (5)
O3	0.0173 (8)	0.0173 (8)	0.0153 (7)	0.0008 (6)	−0.0061 (6)	−0.0004 (6)
O1	0.0241 (8)	0.0104 (7)	0.0188 (8)	−0.0031 (6)	−0.0048 (6)	0.0007 (6)
O2	0.0210 (8)	0.0204 (9)	0.0211 (8)	−0.0015 (6)	−0.0083 (6)	−0.0031 (6)
C6	0.0114 (8)	0.0128 (9)	0.0138 (9)	−0.0012 (7)	0.0009 (7)	−0.0017 (7)
C7	0.0128 (9)	0.0120 (9)	0.0136 (9)	0.0008 (7)	0.0011 (7)	0.0006 (7)
C8	0.0103 (8)	0.0155 (9)	0.0105 (8)	0.0020 (7)	0.0003 (6)	0.0010 (7)
C1	0.0282 (12)	0.0114 (10)	0.0211 (11)	−0.0062 (8)	0.0005 (9)	−0.0021 (8)
C5	0.0178 (10)	0.0137 (10)	0.0158 (9)	−0.0004 (7)	−0.0061 (7)	0.0005 (7)
C3	0.0132 (9)	0.0108 (9)	0.0128 (9)	0.0003 (7)	−0.0010 (7)	0.0004 (7)
C2	0.0140 (9)	0.0152 (10)	0.0138 (9)	−0.0006 (7)	0.0007 (7)	−0.0011 (7)
C4	0.0179 (10)	0.0104 (9)	0.0177 (10)	0.0002 (7)	−0.0053 (8)	0.0012 (7)

Geometric parameters (Å, º)

I1—C6	2.101 (2)	C8—C3	1.407 (3)
O3—C8	1.357 (3)	C1—H1A	0.9800
O3—H3	0.70 (4)	C1—H1B	0.9800
O1—C1	1.447 (3)	C1—H1C	0.9800
O1—C2	1.336 (3)	C5—H5	0.9500
O2—C2	1.220 (3)	C5—C4	1.379 (3)
C6—C7	1.391 (3)	C3—C2	1.472 (3)
C6—C5	1.394 (3)	C3—C4	1.400 (3)
C7—H7	0.9500	C4—H4	0.9500
C7—C8	1.395 (3)
C8—O3—H3	107 (3)	H1A—C1—H1C	109.5
C2—O1—C1	115.15 (18)	H1B—C1—H1C	109.5
C7—C6—I1	119.85 (16)	C6—C5—H5	121.0
C7—C6—C5	121.9 (2)	C4—C5—C6	118.0 (2)
C5—C6—I1	118.20 (15)	C4—C5—H5	121.0
C6—C7—H7	120.3	C8—C3—C2	120.44 (19)
C6—C7—C8	119.4 (2)	C4—C3—C8	118.89 (19)
C8—C7—H7	120.3	C4—C3—C2	120.63 (19)
O3—C8—C7	116.94 (19)	O1—C2—C3	113.23 (18)
O3—C8—C3	123.3 (2)	O2—C2—O1	122.9 (2)
C7—C8—C3	119.80 (19)	O2—C2—C3	123.8 (2)
O1—C1—H1A	109.5	C5—C4—C3	122.0 (2)
O1—C1—H1B	109.5	C5—C4—H4	119.0
O1—C1—H1C	109.5	C3—C4—H4	119.0
H1A—C1—H1B	109.5
I1—C6—C7—C8	178.99 (15)	C8—C3—C2—O1	178.4 (2)
I1—C6—C5—C4	−179.01 (17)	C8—C3—C2—O2	−1.0 (3)
O3—C8—C3—C2	1.0 (3)	C8—C3—C4—C5	0.9 (3)
O3—C8—C3—C4	178.8 (2)	C1—O1—C2—O2	1.2 (3)
C6—C7—C8—O3	−178.90 (19)	C1—O1—C2—C3	−178.26 (19)
C6—C7—C8—C3	0.9 (3)	C5—C6—C7—C8	−0.8 (3)
C6—C5—C4—C3	−0.9 (4)	C2—C3—C4—C5	178.8 (2)
C7—C6—C5—C4	0.8 (3)	C4—C3—C2—O1	0.6 (3)
C7—C8—C3—C2	−178.8 (2)	C4—C3—C2—O2	−178.8 (2)
C7—C8—C3—C4	−0.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.70 (4)	2.05 (4)	2.670 (3)	149 (4)
O3—H3···O2^i	0.70 (4)	2.53 (4)	3.087 (2)	139 (4)

Symmetry code: (i) −x+2, −y+1, −z+2.