1-(4-Methoxy­phenyl)but-3-yn-1-ol

Molecules of the title compound, C₁₁H₁₂O₂, are connected by intermolecular O—H...O hydrogen bonds to form helices running in the b direction. These helices are further stabilized by intermolecular C—H...π(phenyl) interactions.

Key indicators

• Single-crystal X-ray study
• T = 144 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.069
• wR factor = 0.139
• Data-to-parameter ratio = 29.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

---

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

1-(4-methoxyphenyl)-but-3-yn-1-ol

Crystal data

C11H12O2	F(000) = 752
Mr = 176.21	Dx = 1.196 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.734 (3) Å	Cell parameters from 155 reflections
b = 6.5429 (9) Å	θ = 3–23°
c = 20.907 (3) Å	µ = 0.08 mm^−1
β = 103.793 (9)°	T = 144 K
V = 1957.4 (6) Å^3	Parallelepiped, pale_yellow
Z = 8	0.45 × 0.27 × 0.14 mm

Data collection

SIEMENS_SMART_CCD diffractometer	7056 independent reflections
Radiation source: normal-focus sealed tube	4779 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ω scans	θmax = 33.0°, θmin = 1.5°
Absorption correction: numerical (SHELXTL; Sheldrick, 1996)	h = −20→22
Tmin = 0.971, Tmax = 0.990	k = −9→10
41566 measured reflections	l = −32→30

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)] = 0.069	H-atom parameters constrained
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.03P)^2 + 1.P] where P = (Fo^2 + 2Fc^2)/3
S = 1.21	(Δ/σ)max < 0.001
7056 reflections	Δρmax = 0.50 e Å^−3
240 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL-97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0034 (9)

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	0.78559 (7)	0.12786 (16)	0.19088 (5)	0.0254 (2)
H01	0.7597	0.2428	0.1838	0.038*
O2	0.82510 (8)	0.51053 (17)	−0.07801 (5)	0.0319 (3)
O3	0.69653 (8)	−0.50391 (18)	0.18246 (5)	0.0324 (3)
H03	0.7016	−0.4653	0.2215	0.049*
O4	0.30739 (7)	−0.12325 (17)	0.19258 (6)	0.0300 (3)
C1	1.07042 (11)	−0.1397 (3)	0.14716 (8)	0.0318 (3)
H1	1.1286	−0.1613	0.1361	0.038*
C2	0.99817 (11)	−0.1128 (2)	0.16093 (8)	0.0273 (3)
C3	0.90586 (11)	−0.0897 (2)	0.17554 (8)	0.0288 (3)
H3A	0.9086	−0.1434	0.2202	0.035*
H3B	0.8596	−0.1721	0.1438	0.035*
C4	0.87349 (10)	0.1322 (2)	0.17187 (7)	0.0245 (3)
H4	0.9194	0.2137	0.2051	0.029*
C5	0.86287 (10)	0.2296 (2)	0.10516 (7)	0.0228 (3)
C6	0.90626 (11)	0.4139 (2)	0.09994 (7)	0.0260 (3)
H6	0.9444	0.4739	0.1384	0.031*
C7	0.89570 (11)	0.5141 (2)	0.03998 (7)	0.0267 (3)
H7	0.9261	0.6410	0.0376	0.032*
C8	0.84032 (11)	0.4268 (2)	−0.01631 (7)	0.0243 (3)
C9	0.79607 (11)	0.2404 (2)	−0.01229 (8)	0.0281 (3)
H9	0.7583	0.1798	−0.0508	0.034*
C10	0.80725 (11)	0.1442 (2)	0.04793 (8)	0.0281 (3)
H10	0.7766	0.0178	0.0504	0.034*
C11	0.86030 (14)	0.7115 (3)	−0.08300 (9)	0.0401 (4)
H11A	0.8311	0.8068	−0.0578	0.060*
H11B	0.8459	0.7534	−0.1293	0.060*
H11C	0.9282	0.7122	−0.0653	0.060*
C12	0.58746 (14)	−0.1397 (3)	−0.02039 (9)	0.0450 (5)
H12	0.5663	−0.0342	−0.0516	0.054*
C13	0.61370 (12)	−0.2708 (3)	0.01842 (8)	0.0336 (4)
C14	0.64659 (12)	−0.4276 (3)	0.06864 (8)	0.0320 (4)
H14A	0.7085	−0.4781	0.0650	0.038*
H14B	0.6026	−0.5444	0.0609	0.038*
C15	0.65432 (11)	−0.3433 (2)	0.13783 (7)	0.0265 (3)
H15	0.6972	−0.2225	0.1447	0.032*
C16	0.56161 (10)	−0.2796 (2)	0.15098 (7)	0.0228 (3)
C17	0.55148 (10)	−0.0884 (2)	0.17688 (7)	0.0241 (3)
H17	0.6023	0.0049	0.1843	0.029*
C18	0.46794 (10)	−0.0301 (2)	0.19228 (7)	0.0243 (3)
H18	0.4624	0.1009	0.2106	0.029*
C19	0.39318 (10)	−0.1653 (2)	0.18057 (7)	0.0232 (3)
C20	0.40190 (11)	−0.3573 (2)	0.15402 (8)	0.0297 (3)
H20	0.3506	−0.4496	0.1457	0.036*
C21	0.48555 (11)	−0.4132 (2)	0.13984 (8)	0.0296 (3)
H21	0.4914	−0.5451	0.1222	0.035*
C22	0.30133 (12)	0.0503 (3)	0.23252 (9)	0.0363 (4)
H22A	0.3475	0.0378	0.2747	0.054*
H22B	0.2385	0.0579	0.2405	0.054*
H22C	0.3138	0.1746	0.2099	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0258 (5)	0.0255 (5)	0.0276 (5)	0.0041 (4)	0.0118 (4)	0.0029 (4)
O2	0.0437 (7)	0.0285 (6)	0.0244 (5)	0.0002 (5)	0.0100 (5)	0.0042 (4)
O3	0.0357 (6)	0.0371 (6)	0.0240 (5)	0.0157 (5)	0.0061 (5)	0.0000 (5)
O4	0.0215 (5)	0.0333 (6)	0.0376 (6)	−0.0013 (4)	0.0114 (5)	−0.0090 (5)
C1	0.0283 (8)	0.0294 (8)	0.0388 (9)	0.0019 (6)	0.0101 (7)	0.0028 (7)
C2	0.0285 (8)	0.0250 (7)	0.0276 (7)	0.0020 (6)	0.0054 (6)	0.0019 (6)
C3	0.0279 (8)	0.0254 (7)	0.0347 (8)	0.0015 (6)	0.0108 (6)	0.0032 (6)
C4	0.0242 (7)	0.0251 (7)	0.0252 (7)	0.0009 (6)	0.0080 (6)	0.0010 (6)
C5	0.0237 (7)	0.0229 (7)	0.0236 (7)	0.0035 (5)	0.0091 (5)	0.0009 (5)
C6	0.0267 (7)	0.0258 (7)	0.0249 (7)	−0.0005 (6)	0.0051 (6)	−0.0024 (6)
C7	0.0288 (8)	0.0228 (7)	0.0292 (7)	−0.0020 (6)	0.0085 (6)	0.0007 (6)
C8	0.0281 (7)	0.0238 (7)	0.0235 (7)	0.0038 (6)	0.0110 (6)	0.0018 (6)
C9	0.0334 (8)	0.0251 (7)	0.0251 (7)	−0.0022 (6)	0.0053 (6)	−0.0034 (6)
C10	0.0328 (8)	0.0213 (7)	0.0306 (8)	−0.0037 (6)	0.0082 (6)	0.0009 (6)
C11	0.0506 (11)	0.0318 (9)	0.0389 (10)	0.0012 (8)	0.0129 (8)	0.0129 (8)
C12	0.0503 (12)	0.0519 (12)	0.0302 (9)	−0.0006 (9)	0.0046 (8)	0.0044 (8)
C13	0.0304 (8)	0.0458 (10)	0.0251 (7)	−0.0008 (7)	0.0075 (6)	−0.0034 (7)
C14	0.0309 (8)	0.0388 (9)	0.0278 (8)	0.0064 (7)	0.0100 (6)	−0.0023 (7)
C15	0.0249 (7)	0.0302 (8)	0.0250 (7)	0.0039 (6)	0.0070 (6)	−0.0008 (6)
C16	0.0213 (7)	0.0268 (7)	0.0201 (6)	0.0029 (6)	0.0047 (5)	0.0009 (5)
C17	0.0204 (7)	0.0254 (7)	0.0255 (7)	−0.0014 (5)	0.0034 (5)	−0.0001 (6)
C18	0.0239 (7)	0.0219 (7)	0.0267 (7)	0.0001 (5)	0.0053 (6)	−0.0019 (6)
C19	0.0199 (7)	0.0264 (7)	0.0237 (7)	0.0020 (5)	0.0061 (5)	−0.0003 (6)
C20	0.0273 (8)	0.0252 (8)	0.0379 (8)	−0.0055 (6)	0.0106 (7)	−0.0068 (6)
C21	0.0319 (8)	0.0234 (7)	0.0347 (8)	0.0007 (6)	0.0107 (7)	−0.0069 (6)
C22	0.0311 (9)	0.0366 (9)	0.0435 (10)	0.0034 (7)	0.0135 (7)	−0.0123 (8)

Geometric parameters (Å, º)

O1—C4	1.4427 (17)	C10—H10	0.9500
O1—H01	0.8400	C11—H11A	0.9800
O2—C8	1.3698 (17)	C11—H11B	0.9800
O2—C11	1.426 (2)	C11—H11C	0.9800
O3—C15	1.4440 (19)	C12—C13	1.181 (3)
O3—H03	0.8400	C12—H12	0.9500
O4—C19	1.3741 (17)	C13—C14	1.465 (2)
O4—C22	1.4248 (19)	C14—C15	1.527 (2)
C1—C2	1.180 (2)	C14—H14A	0.9900
C1—H1	0.9500	C14—H14B	0.9900
C2—C3	1.471 (2)	C15—C16	1.515 (2)
C3—C4	1.524 (2)	C15—H15	1.0000
C3—H3A	0.9900	C16—C17	1.385 (2)
C3—H3B	0.9900	C16—C21	1.397 (2)
C4—C5	1.507 (2)	C17—C18	1.398 (2)
C4—H4	1.0000	C17—H17	0.9500
C5—C6	1.381 (2)	C18—C19	1.388 (2)
C5—C10	1.396 (2)	C18—H18	0.9500
C6—C7	1.390 (2)	C19—C20	1.392 (2)
C6—H6	0.9500	C20—C21	1.384 (2)
C7—C8	1.385 (2)	C20—H20	0.9500
C7—H7	0.9500	C21—H21	0.9500
C8—C9	1.395 (2)	C22—H22A	0.9800
C9—C10	1.382 (2)	C22—H22B	0.9800
C9—H9	0.9500	C22—H22C	0.9800
C4—O1—H01	109.5	H11A—C11—H11C	109.5
C8—O2—C11	117.17 (13)	H11B—C11—H11C	109.5
C15—O3—H03	109.5	C13—C12—H12	180.0
C19—O4—C22	117.10 (12)	C12—C13—C14	177.76 (19)
C2—C1—H1	180.0	C13—C14—C15	111.28 (14)
C1—C2—C3	176.59 (18)	C13—C14—H14A	109.4
C2—C3—C4	112.40 (13)	C15—C14—H14A	109.4
C2—C3—H3A	109.1	C13—C14—H14B	109.4
C4—C3—H3A	109.1	C15—C14—H14B	109.4
C2—C3—H3B	109.1	H14A—C14—H14B	108.0
C4—C3—H3B	109.1	O3—C15—C16	110.56 (12)
H3A—C3—H3B	107.9	O3—C15—C14	105.81 (12)
O1—C4—C5	111.17 (12)	C16—C15—C14	113.87 (13)
O1—C4—C3	104.96 (11)	O3—C15—H15	108.8
C5—C4—C3	114.29 (12)	C16—C15—H15	108.8
O1—C4—H4	108.7	C14—C15—H15	108.8
C5—C4—H4	108.7	C17—C16—C21	118.27 (13)
C3—C4—H4	108.7	C17—C16—C15	120.36 (13)
C6—C5—C10	118.03 (13)	C21—C16—C15	121.33 (14)
C6—C5—C4	119.62 (13)	C16—C17—C18	121.31 (14)
C10—C5—C4	122.30 (13)	C16—C17—H17	119.3
C5—C6—C7	121.92 (14)	C18—C17—H17	119.3
C5—C6—H6	119.0	C19—C18—C17	119.37 (14)
C7—C6—H6	119.0	C19—C18—H18	120.3
C8—C7—C6	119.22 (14)	C17—C18—H18	120.3
C8—C7—H7	120.4	O4—C19—C18	124.47 (13)
C6—C7—H7	120.4	O4—C19—C20	115.47 (13)
O2—C8—C7	124.49 (14)	C18—C19—C20	120.06 (13)
O2—C8—C9	115.62 (14)	C21—C20—C19	119.72 (14)
C7—C8—C9	119.89 (14)	C21—C20—H20	120.1
C10—C9—C8	119.83 (14)	C19—C20—H20	120.1
C10—C9—H9	120.1	C20—C21—C16	121.26 (14)
C8—C9—H9	120.1	C20—C21—H21	119.4
C9—C10—C5	121.11 (14)	C16—C21—H21	119.4
C9—C10—H10	119.4	O4—C22—H22A	109.5
C5—C10—H10	119.4	O4—C22—H22B	109.5
O2—C11—H11A	109.5	H22A—C22—H22B	109.5
O2—C11—H11B	109.5	O4—C22—H22C	109.5
H11A—C11—H11B	109.5	H22A—C22—H22C	109.5
O2—C11—H11C	109.5	H22B—C22—H22C	109.5
C2—C3—C4—O1	−176.93 (12)	C13—C14—C15—O3	−173.95 (13)
C2—C3—C4—C5	61.02 (18)	C13—C14—C15—C16	64.42 (18)
O1—C4—C5—C6	113.50 (15)	O3—C15—C16—C17	111.58 (15)
C3—C4—C5—C6	−127.92 (15)	C14—C15—C16—C17	−129.47 (15)
O1—C4—C5—C10	−63.89 (18)	O3—C15—C16—C21	−65.98 (18)
C3—C4—C5—C10	54.69 (19)	C14—C15—C16—C21	53.0 (2)
C10—C5—C6—C7	0.1 (2)	C21—C16—C17—C18	0.7 (2)
C4—C5—C6—C7	−177.40 (14)	C15—C16—C17—C18	−176.97 (14)
C5—C6—C7—C8	−0.2 (2)	C16—C17—C18—C19	−0.9 (2)
C11—O2—C8—C7	−7.3 (2)	C22—O4—C19—C18	−14.3 (2)
C11—O2—C8—C9	173.04 (14)	C22—O4—C19—C20	166.61 (14)
C6—C7—C8—O2	−179.66 (14)	C17—C18—C19—O4	−178.75 (14)
C6—C7—C8—C9	0.0 (2)	C17—C18—C19—C20	0.3 (2)
O2—C8—C9—C10	−179.99 (14)	O4—C19—C20—C21	179.61 (14)
C7—C8—C9—C10	0.4 (2)	C18—C19—C20—C21	0.5 (2)
C8—C9—C10—C5	−0.5 (2)	C19—C20—C21—C16	−0.7 (2)
C6—C5—C10—C9	0.2 (2)	C17—C16—C21—C20	0.1 (2)
C4—C5—C10—C9	177.66 (14)	C15—C16—C21—C20	177.74 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O3^i	0.84	1.90	2.7290 (17)	170
O3—H03···O1^ii	0.84	1.90	2.7372 (16)	179
C4—H4···Cg2^iii	1.00	2.80	3.704 (2)	151
C11—H11C···Cg1^iv	0.98	3.18	4.138 (2)	165
C12—H12···Cg2^v	0.95	2.86	3.791 (2)	166
C14—H14A···Cg1^vi	0.99	2.58	3.559 (2)	169

Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y, −z; (vi) x, y−1, z.