(2,4-Dichloro­phen­yl)methanol

The title compound, C₇H₆Cl₂O, also known as 2,4-dichloro­benzyl alcohol, has anti­microbial properties and is widely used in pharmaceuticals. It crystallizes with two independent mol­ecules in the asymmetric unit. The packing in the solid is characterized by the presence of ribbons of O—H...O hydrogen-bonded mol­ecules, parallel to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.027
• wR factor = 0.074
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      64.89 Deg.

Author Response: 'see _publ_section_exptl_refinement'

Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5873
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6].....      64.89 Deg.
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.41
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C7 H6 Cl2 O

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.409
            Tmax scaled      0.488 Tmin scaled      0.205

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(2,4-Dichlorophenyl)methanol

Crystal data

C7H6Cl2O	F(000) = 720
Mr = 177.02	Dx = 1.570 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 2776 reflections
a = 4.7361 (4) Å	θ = 8.8–44.5°
b = 12.8179 (13) Å	µ = 7.17 mm^−1
c = 24.853 (2) Å	T = 296 K
β = 96.852 (8)°	Elongated prism, colorless
V = 1498.0 (2) Å^3	0.60 × 0.20 × 0.10 mm
Z = 8

Data collection

Oxford Diffraction Excalibur PX Ultra CCD diffractometer	2543 independent reflections
Radiation source: fine-focus sealed tube	1967 reflections with I > 2σ(I)
Oxford Diffraction, Enhance ULTRA assembly monochromator	Rint = 0.027
ω scans	θmax = 64.9°, θmin = 3.9°
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2006)	h = −5→5
Tmin = 0.502, Tmax = 1.194	k = −15→15
15434 measured reflections	l = −28→28

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + ] where P = (Fo^2 + 2Fc^2)/3
2543 reflections	(Δ/σ)max = 0.001
188 parameters	Δρmax = 0.31 e Å^−3
2 restraints	Δρmin = −0.24 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 > 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
O1	−0.3412 (2)	−0.33182 (9)	0.08544 (6)	0.0332 (3)
H1	−0.199 (4)	−0.3001 (17)	0.0849 (9)	0.050*
C1	−0.0724 (3)	−0.49377 (12)	0.10396 (7)	0.0218 (4)
C2	0.0037 (3)	−0.59531 (13)	0.09104 (7)	0.0218 (4)
C3	0.2162 (3)	−0.65071 (13)	0.12152 (7)	0.0232 (4)
H3	0.2627	−0.7181	0.1118	0.028*
C4	0.3576 (3)	−0.60303 (13)	0.16687 (7)	0.0243 (4)
C5	0.2897 (3)	−0.50290 (13)	0.18159 (7)	0.0265 (4)
H5	0.3866	−0.4717	0.2122	0.032*
C6	0.0750 (3)	−0.44973 (13)	0.15009 (7)	0.0248 (4)
H6	0.0283	−0.3826	0.1601	0.030*
C7	−0.3027 (3)	−0.43578 (12)	0.06862 (8)	0.0260 (4)
H7A	−0.2555	−0.4351	0.0317	0.031*
H7B	−0.4806	−0.4732	0.0687	0.031*
Cl1	−0.17824 (9)	−0.65641 (3)	0.034290 (18)	0.03096 (14)
Cl2	0.62473 (8)	−0.67190 (3)	0.206185 (18)	0.03257 (14)
O2	0.1639 (2)	−0.22837 (9)	0.09230 (5)	0.0291 (3)
H2	0.302 (4)	−0.2614 (16)	0.0895 (9)	0.044*
C8	0.4364 (3)	−0.06667 (12)	0.10795 (7)	0.0213 (4)
C9	0.5049 (3)	0.03553 (13)	0.09494 (7)	0.0210 (4)
C10	0.7181 (3)	0.09214 (13)	0.12465 (7)	0.0230 (4)
H10	0.7607	0.1598	0.1148	0.028*
C11	0.8656 (3)	0.04490 (13)	0.16950 (7)	0.0234 (4)
C12	0.8060 (3)	−0.05590 (13)	0.18422 (7)	0.0261 (4)
H12	0.9085	−0.0868	0.2143	0.031*
C13	0.5905 (3)	−0.11035 (13)	0.15341 (7)	0.0242 (4)
H13	0.5484	−0.1779	0.1635	0.029*
C14	0.2031 (3)	−0.12562 (12)	0.07371 (7)	0.0233 (4)
H14A	0.0261	−0.0875	0.0735	0.028*
H14B	0.2485	−0.1287	0.0367	0.028*
Cl3	0.31036 (9)	0.09630 (3)	0.039398 (17)	0.02877 (13)
Cl4	1.13120 (9)	0.11571 (3)	0.208107 (19)	0.03236 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0187 (7)	0.0205 (6)	0.0604 (10)	0.0008 (5)	0.0048 (6)	−0.0011 (6)
C1	0.0179 (9)	0.0217 (8)	0.0269 (10)	−0.0019 (7)	0.0079 (7)	0.0015 (7)
C2	0.0209 (9)	0.0233 (8)	0.0216 (9)	−0.0034 (7)	0.0048 (7)	−0.0023 (7)
C3	0.0208 (9)	0.0216 (8)	0.0281 (10)	−0.0007 (7)	0.0068 (8)	0.0000 (7)
C4	0.0186 (9)	0.0275 (9)	0.0269 (10)	−0.0014 (7)	0.0038 (7)	0.0047 (7)
C5	0.0266 (9)	0.0280 (9)	0.0251 (10)	−0.0063 (7)	0.0043 (8)	−0.0039 (8)
C6	0.0249 (9)	0.0210 (8)	0.0299 (10)	−0.0020 (7)	0.0086 (7)	−0.0031 (7)
C7	0.0210 (9)	0.0222 (8)	0.0346 (11)	−0.0005 (7)	0.0033 (7)	−0.0002 (8)
Cl1	0.0332 (3)	0.0275 (2)	0.0302 (3)	0.00046 (17)	−0.00469 (19)	−0.00542 (18)
Cl2	0.0256 (3)	0.0349 (3)	0.0354 (3)	0.00205 (17)	−0.0042 (2)	0.00320 (19)
O2	0.0198 (6)	0.0211 (6)	0.0467 (8)	−0.0009 (5)	0.0051 (6)	−0.0021 (6)
C8	0.0172 (8)	0.0235 (8)	0.0245 (10)	0.0013 (6)	0.0073 (7)	−0.0021 (7)
C9	0.0192 (9)	0.0228 (8)	0.0216 (9)	0.0043 (6)	0.0039 (7)	0.0018 (7)
C10	0.0209 (9)	0.0218 (8)	0.0274 (10)	0.0005 (7)	0.0068 (7)	0.0001 (7)
C11	0.0172 (9)	0.0271 (9)	0.0258 (10)	−0.0013 (7)	0.0028 (7)	−0.0052 (7)
C12	0.0241 (9)	0.0303 (9)	0.0237 (10)	0.0054 (7)	0.0019 (7)	0.0016 (8)
C13	0.0246 (9)	0.0210 (8)	0.0281 (10)	0.0003 (7)	0.0076 (8)	0.0011 (7)
C14	0.0191 (9)	0.0240 (8)	0.0270 (10)	0.0000 (7)	0.0039 (7)	−0.0010 (7)
Cl3	0.0292 (3)	0.0283 (2)	0.0276 (3)	0.00328 (17)	−0.00126 (18)	0.00402 (18)
Cl4	0.0238 (3)	0.0354 (3)	0.0361 (3)	−0.00426 (17)	−0.00373 (19)	−0.00466 (19)

Geometric parameters (Å, º)

C7—O1	1.415 (2)	C14—O2	1.415 (2)
O1—H1	0.786 (17)	O2—H2	0.789 (17)
C1—C6	1.389 (2)	C8—C13	1.388 (2)
C1—C2	1.398 (2)	C8—C9	1.397 (2)
C1—C7	1.512 (2)	C8—C14	1.514 (2)
C2—C3	1.382 (2)	C9—C10	1.383 (2)
C2—Cl1	1.7480 (17)	C9—Cl3	1.7487 (16)
C3—C4	1.383 (2)	C10—C11	1.383 (2)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.383 (2)	C11—C12	1.381 (2)
C4—Cl2	1.7434 (17)	C11—Cl4	1.7432 (17)
C5—C6	1.386 (2)	C12—C13	1.389 (2)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—H7A	0.9700	C14—H14A	0.9700
C7—H7B	0.9700	C14—H14B	0.9700
C7—O1—H1	110.0 (17)	C14—O2—H2	109.1 (16)
C6—C1—C2	116.74 (15)	C13—C8—C9	116.91 (15)
C6—C1—C7	122.44 (14)	C13—C8—C14	122.28 (15)
C2—C1—C7	120.82 (15)	C9—C8—C14	120.81 (15)
C3—C2—C1	122.92 (16)	C10—C9—C8	122.92 (15)
C3—C2—Cl1	117.96 (13)	C10—C9—Cl3	118.03 (13)
C1—C2—Cl1	119.12 (13)	C8—C9—Cl3	119.04 (13)
C2—C3—C4	118.03 (15)	C11—C10—C9	117.84 (15)
C2—C3—H3	121.0	C11—C10—H10	121.1
C4—C3—H3	121.0	C9—C10—H10	121.1
C3—C4—C5	121.35 (16)	C12—C11—C10	121.58 (16)
C3—C4—Cl2	118.79 (13)	C12—C11—Cl4	119.87 (13)
C5—C4—Cl2	119.86 (14)	C10—C11—Cl4	118.55 (13)
C4—C5—C6	119.02 (16)	C11—C12—C13	118.95 (16)
C4—C5—H5	120.5	C11—C12—H12	120.5
C6—C5—H5	120.5	C13—C12—H12	120.5
C5—C6—C1	121.93 (15)	C8—C13—C12	121.79 (16)
C5—C6—H6	119.0	C8—C13—H13	119.1
C1—C6—H6	119.0	C12—C13—H13	119.1
O1—C7—C1	113.64 (14)	O2—C14—C8	113.35 (14)
O1—C7—H7A	108.8	O2—C14—H14A	108.9
C1—C7—H7A	108.8	C8—C14—H14A	108.9
O1—C7—H7B	108.8	O2—C14—H14B	108.9
C1—C7—H7B	108.8	C8—C14—H14B	108.9
H7A—C7—H7B	107.7	H14A—C14—H14B	107.7
C6—C1—C2—C3	−0.7 (2)	C13—C8—C9—C10	1.0 (2)
C7—C1—C2—C3	178.80 (15)	C14—C8—C9—C10	−179.32 (14)
C6—C1—C2—Cl1	178.70 (12)	C13—C8—C9—Cl3	−177.95 (12)
C7—C1—C2—Cl1	−1.8 (2)	C14—C8—C9—Cl3	1.8 (2)
C1—C2—C3—C4	0.3 (2)	C8—C9—C10—C11	−0.8 (2)
Cl1—C2—C3—C4	−179.09 (12)	Cl3—C9—C10—C11	178.09 (12)
C2—C3—C4—C5	0.0 (2)	C9—C10—C11—C12	0.7 (2)
C2—C3—C4—Cl2	179.55 (12)	C9—C10—C11—Cl4	−178.97 (12)
C3—C4—C5—C6	0.1 (2)	C10—C11—C12—C13	−0.7 (3)
Cl2—C4—C5—C6	−179.45 (12)	Cl4—C11—C12—C13	178.98 (12)
C4—C5—C6—C1	−0.5 (2)	C9—C8—C13—C12	−0.9 (2)
C2—C1—C6—C5	0.8 (2)	C14—C8—C13—C12	179.36 (15)
C7—C1—C6—C5	−178.70 (15)	C11—C12—C13—C8	0.8 (3)
C6—C1—C7—O1	3.2 (2)	C13—C8—C14—O2	−0.9 (2)
C2—C1—C7—O1	−176.25 (14)	C9—C8—C14—O2	179.35 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.79 (2)	1.94 (2)	2.7228 (16)	173 (2)
O2—H2···O1^i	0.79 (2)	1.93 (2)	2.7158 (16)	175 (2)

Symmetry code: (i) x+1, y, z.