An exploration of O—H...O and C—H...π inter­actions in a long-chain-ester-substituted phenyl­phenol: methyl 10-[4-(4-hydroxyphenyl)phenoxy]decanoate

The superstructure of 4-(9-methyl­oxycarbonyl­non­yloxy)phenyl­phenol is dominated by O—H...O and C—H...O hydrogen-bonding and C—H...π inter­actions. Hirshfeld surface, fingerprint plot, inter­action energy and energy framework analyses were used to explore the nature and strength of the inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.044
• wR factor = 0.122
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C22 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.005 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23A     ..O3               2.74 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3       ..O2               2.82 Ang.
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         65 %
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          6 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Methyl 10-[4-(4-hydroxyphenyl)phenoxy]decanoate

Crystal data

C23H30O4	F(000) = 800
Mr = 370.47	Dx = 1.192 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 42.287 (9) Å	Cell parameters from 122 reflections
b = 7.2848 (15) Å	θ = 3.1–19.4°
c = 6.7006 (13) Å	µ = 0.08 mm^−1
β = 91.226 (12)°	T = 200 K
V = 2063.7 (7) Å^3	Plate, clear colorless
Z = 4	0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART X2S benchtop diffractometer	3095 independent reflections
Radiation source: sealed microfocus tube	2363 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.060
Detector resolution: 8.3330 pixels mm^-1	θmax = 25.3°, θmin = 2.8°
ω scans	h = −44→50
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −8→8
Tmin = 0.64, Tmax = 0.98	l = −8→8
10387 measured reflections

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)] = 0.044	Hydrogen site location: mixed
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.063P)^2 + 0.2432P] where P = (Fo^2 + 2Fc^2)/3
3095 reflections	(Δ/σ)max < 0.001
249 parameters	Δρmax = 0.12 e Å^−3
2 restraints	Δρmin = −0.18 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
O1	0.73167 (7)	0.2440 (4)	−0.5378 (5)	0.0736 (9)
H1	0.7463 (10)	0.294 (5)	−0.458 (7)	0.077 (14)*
O2	0.51725 (5)	0.2275 (3)	0.0196 (3)	0.0512 (7)
O3	0.28496 (7)	0.1690 (4)	1.2022 (5)	0.0826 (9)
O4	0.29945 (7)	0.3224 (4)	1.4752 (4)	0.0800 (9)
C1	0.60847 (8)	0.2531 (4)	−0.2156 (5)	0.0383 (8)
C2	0.58278 (8)	0.1710 (5)	−0.3145 (5)	0.0442 (8)
H2	0.5858	0.1167	−0.4415	0.053*
C3	0.55318 (8)	0.1662 (5)	−0.2339 (5)	0.0447 (8)
H3	0.5364	0.108	−0.3058	0.054*
C4	0.54735 (8)	0.2444 (5)	−0.0505 (5)	0.0401 (9)
C5	0.57240 (9)	0.3313 (5)	0.0505 (5)	0.0508 (9)
H5	0.569	0.3892	0.1753	0.061*
C6	0.60217 (8)	0.3326 (4)	−0.0319 (6)	0.0499 (9)
H6	0.619	0.3903	0.0402	0.06*
C7	0.64072 (7)	0.2542 (4)	−0.3000 (5)	0.0392 (8)
C8	0.64804 (9)	0.1590 (5)	−0.4734 (6)	0.0600 (10)
H8	0.6317	0.0942	−0.5427	0.072*
C9	0.67810 (9)	0.1556 (5)	−0.5479 (6)	0.0662 (11)
H9	0.6822	0.0868	−0.665	0.079*
C10	0.70209 (8)	0.2498 (4)	−0.4554 (6)	0.0522 (10)
C11	0.69596 (9)	0.3481 (5)	−0.2861 (6)	0.0600 (10)
H11	0.7124	0.4153	−0.2207	0.072*
C12	0.66573 (8)	0.3490 (5)	−0.2107 (5)	0.0552 (10)
H12	0.6619	0.4174	−0.0929	0.066*
C13	0.51112 (8)	0.2887 (5)	0.2186 (5)	0.0469 (9)
H13A	0.5118	0.4244	0.2255	0.056*
H13B	0.5272	0.2385	0.3135	0.056*
C14	0.47868 (8)	0.2203 (5)	0.2700 (6)	0.0483 (9)
H14A	0.4788	0.0844	0.2685	0.058*
H14B	0.4633	0.2624	0.1663	0.058*
C15	0.46794 (8)	0.2860 (4)	0.4725 (5)	0.0437 (8)
H15A	0.4682	0.4219	0.4748	0.052*
H15B	0.4831	0.2421	0.5766	0.052*
C16	0.43495 (8)	0.2191 (4)	0.5219 (5)	0.0426 (8)
H16A	0.4199	0.2639	0.4178	0.051*
H16B	0.4348	0.0832	0.5171	0.051*
C17	0.42356 (8)	0.2799 (4)	0.7235 (5)	0.0429 (8)
H17A	0.424	0.4157	0.7289	0.052*
H17B	0.4385	0.2338	0.8276	0.052*
C18	0.39041 (9)	0.2150 (4)	0.7728 (5)	0.0448 (8)
H18A	0.3754	0.261	0.6691	0.054*
H18B	0.3899	0.0792	0.7683	0.054*
C19	0.37950 (8)	0.2779 (4)	0.9753 (5)	0.0442 (8)
H19A	0.3811	0.4134	0.9811	0.053*
H19B	0.3942	0.2279	1.0785	0.053*
C20	0.34601 (8)	0.2228 (5)	1.0281 (5)	0.0469 (9)
H20A	0.331	0.2703	0.9249	0.056*
H20B	0.3444	0.0873	1.0291	0.056*
C21	0.33705 (9)	0.2965 (5)	1.2292 (6)	0.0546 (10)
H21A	0.3522	0.2475	1.3304	0.066*
H21B	0.3396	0.4316	1.2272	0.066*
C22	0.30427 (9)	0.2536 (5)	1.2951 (6)	0.0529 (9)
C23	0.26842 (13)	0.2933 (7)	1.5605 (9)	0.0984 (18)
H23A	0.2635	0.1618	1.5605	0.148*
H23B	0.2524	0.3589	1.4805	0.148*
H23C	0.2685	0.3397	1.6978	0.148*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0492 (17)	0.092 (2)	0.080 (2)	−0.0003 (13)	0.0247 (15)	−0.0105 (16)
O2	0.0425 (14)	0.0684 (17)	0.0429 (15)	−0.0038 (12)	0.0052 (12)	−0.0054 (12)
O3	0.0494 (15)	0.109 (2)	0.090 (2)	−0.0115 (16)	0.0097 (14)	−0.0197 (19)
O4	0.076 (2)	0.100 (2)	0.0656 (19)	−0.0162 (16)	0.0320 (16)	−0.0190 (17)
C1	0.046 (2)	0.0295 (16)	0.040 (2)	0.0002 (12)	0.0028 (15)	0.0012 (13)
C2	0.048 (2)	0.0502 (19)	0.0340 (19)	−0.0005 (15)	0.0007 (15)	−0.0056 (15)
C3	0.0430 (18)	0.049 (2)	0.042 (2)	−0.0037 (14)	−0.0013 (15)	−0.0019 (15)
C4	0.0399 (19)	0.0411 (19)	0.040 (2)	0.0010 (14)	0.0033 (16)	0.0048 (15)
C5	0.054 (2)	0.052 (2)	0.047 (2)	−0.0067 (16)	0.0087 (17)	−0.0128 (17)
C6	0.045 (2)	0.0500 (18)	0.055 (2)	−0.0121 (14)	0.0052 (15)	−0.0159 (16)
C7	0.045 (2)	0.0299 (16)	0.043 (2)	0.0006 (12)	0.0043 (16)	−0.0003 (13)
C8	0.055 (2)	0.066 (2)	0.060 (2)	−0.0132 (16)	0.0147 (18)	−0.0250 (19)
C9	0.061 (2)	0.071 (2)	0.066 (3)	−0.0080 (19)	0.021 (2)	−0.0298 (19)
C10	0.048 (2)	0.049 (2)	0.060 (3)	0.0047 (15)	0.0116 (18)	0.0014 (17)
C11	0.047 (2)	0.069 (2)	0.064 (3)	−0.0045 (16)	0.0020 (19)	−0.012 (2)
C12	0.048 (2)	0.067 (2)	0.051 (2)	−0.0021 (16)	0.0061 (18)	−0.0191 (17)
C13	0.047 (2)	0.053 (2)	0.040 (2)	−0.0002 (15)	0.0056 (16)	−0.0014 (16)
C14	0.048 (2)	0.051 (2)	0.046 (2)	−0.0051 (15)	0.0042 (16)	−0.0068 (17)
C15	0.0403 (18)	0.051 (2)	0.040 (2)	0.0011 (15)	0.0004 (15)	−0.0007 (16)
C16	0.0392 (18)	0.0465 (19)	0.042 (2)	−0.0024 (14)	0.0000 (15)	−0.0047 (16)
C17	0.0442 (19)	0.0486 (19)	0.0359 (19)	0.0004 (15)	−0.0003 (15)	0.0005 (16)
C18	0.0471 (19)	0.047 (2)	0.040 (2)	0.0001 (15)	−0.0005 (14)	−0.0055 (17)
C19	0.044 (2)	0.0509 (19)	0.0374 (19)	−0.0005 (15)	−0.0007 (16)	0.0000 (16)
C20	0.045 (2)	0.052 (2)	0.043 (2)	−0.0011 (15)	0.0009 (16)	−0.0029 (17)
C21	0.050 (2)	0.070 (3)	0.043 (2)	−0.0068 (17)	0.0075 (17)	−0.0075 (18)
C22	0.049 (2)	0.055 (2)	0.056 (3)	0.0026 (17)	0.0095 (18)	0.002 (2)
C23	0.090 (4)	0.100 (4)	0.108 (5)	−0.009 (3)	0.061 (3)	−0.008 (3)

Geometric parameters (Å, º)

O1—C10	1.378 (4)	C13—H13A	0.99
O1—H1	0.89 (4)	C13—H13B	0.99
O2—C4	1.372 (4)	C14—C15	1.518 (5)
O2—C13	1.435 (4)	C14—H14A	0.99
O3—C22	1.188 (5)	C14—H14B	0.99
O4—C22	1.327 (5)	C15—C16	1.521 (4)
O4—C23	1.458 (5)	C15—H15A	0.99
C1—C6	1.391 (5)	C15—H15B	0.99
C1—C2	1.395 (4)	C16—C17	1.511 (4)
C1—C7	1.487 (3)	C16—H16A	0.99
C2—C3	1.374 (4)	C16—H16B	0.99
C2—H2	0.95	C17—C18	1.522 (4)
C3—C4	1.381 (5)	C17—H17A	0.99
C3—H3	0.95	C17—H17B	0.99
C4—C5	1.396 (5)	C18—C19	1.514 (5)
C5—C6	1.385 (5)	C18—H18A	0.99
C5—H5	0.95	C18—H18B	0.99
C6—H6	0.95	C19—C20	1.521 (4)
C7—C12	1.388 (4)	C19—H19A	0.99
C7—C8	1.394 (5)	C19—H19B	0.99
C8—C9	1.376 (5)	C20—C21	1.506 (5)
C8—H8	0.95	C20—H20A	0.99
C9—C10	1.363 (5)	C20—H20B	0.99
C9—H9	0.95	C21—C22	1.497 (5)
C10—C11	1.371 (5)	C21—H21A	0.99
C11—C12	1.385 (5)	C21—H21B	0.99
C11—H11	0.95	C23—H23A	0.98
C12—H12	0.95	C23—H23B	0.98
C13—C14	1.506 (4)	C23—H23C	0.98
C10—O1—H1	112 (3)	C14—C15—C16	112.8 (3)
C4—O2—C13	118.5 (2)	C14—C15—H15A	109.0
C22—O4—C23	117.3 (3)	C16—C15—H15A	109.0
C6—C1—C2	115.9 (3)	C14—C15—H15B	109.0
C6—C1—C7	121.9 (3)	C16—C15—H15B	109.0
C2—C1—C7	122.2 (3)	H15A—C15—H15B	107.8
C3—C2—C1	122.1 (3)	C17—C16—C15	114.3 (2)
C3—C2—H2	119.0	C17—C16—H16A	108.7
C1—C2—H2	119.0	C15—C16—H16A	108.7
C2—C3—C4	121.4 (3)	C17—C16—H16B	108.7
C2—C3—H3	119.3	C15—C16—H16B	108.7
C4—C3—H3	119.3	H16A—C16—H16B	107.6
O2—C4—C3	116.9 (3)	C16—C17—C18	114.6 (2)
O2—C4—C5	125.1 (3)	C16—C17—H17A	108.6
C3—C4—C5	118.0 (3)	C18—C17—H17A	108.6
C6—C5—C4	119.7 (3)	C16—C17—H17B	108.6
C6—C5—H5	120.1	C18—C17—H17B	108.6
C4—C5—H5	120.1	H17A—C17—H17B	107.6
C5—C6—C1	122.9 (3)	C19—C18—C17	113.6 (3)
C5—C6—H6	118.6	C19—C18—H18A	108.9
C1—C6—H6	118.6	C17—C18—H18A	108.9
C12—C7—C8	115.2 (3)	C19—C18—H18B	108.9
C12—C7—C1	122.3 (3)	C17—C18—H18B	108.9
C8—C7—C1	122.4 (3)	H18A—C18—H18B	107.7
C9—C8—C7	122.3 (3)	C18—C19—C20	115.6 (3)
C9—C8—H8	118.8	C18—C19—H19A	108.4
C7—C8—H8	118.8	C20—C19—H19A	108.4
C10—C9—C8	120.7 (3)	C18—C19—H19B	108.4
C10—C9—H9	119.6	C20—C19—H19B	108.4
C8—C9—H9	119.6	H19A—C19—H19B	107.4
C9—C10—C11	119.1 (3)	C21—C20—C19	111.5 (3)
C9—C10—O1	118.4 (3)	C21—C20—H20A	109.3
C11—C10—O1	122.5 (3)	C19—C20—H20A	109.3
C10—C11—C12	119.8 (3)	C21—C20—H20B	109.3
C10—C11—H11	120.1	C19—C20—H20B	109.3
C12—C11—H11	120.1	H20A—C20—H20B	108.0
C11—C12—C7	122.8 (3)	C22—C21—C20	116.2 (3)
C11—C12—H12	118.6	C22—C21—H21A	108.2
C7—C12—H12	118.6	C20—C21—H21A	108.2
O2—C13—C14	107.0 (3)	C22—C21—H21B	108.2
O2—C13—H13A	110.3	C20—C21—H21B	108.2
C14—C13—H13A	110.3	H21A—C21—H21B	107.4
O2—C13—H13B	110.3	O3—C22—O4	123.7 (4)
C14—C13—H13B	110.3	O3—C22—C21	125.7 (4)
H13A—C13—H13B	108.6	O4—C22—C21	110.5 (3)
C13—C14—C15	113.0 (3)	O4—C23—H23A	109.5
C13—C14—H14A	109.0	O4—C23—H23B	109.5
C15—C14—H14A	109.0	H23A—C23—H23B	109.5
C13—C14—H14B	109.0	O4—C23—H23C	109.5
C15—C14—H14B	109.0	H23A—C23—H23C	109.5
H14A—C14—H14B	107.8	H23B—C23—H23C	109.5
C6—C1—C2—C3	−1.0 (4)	C8—C9—C10—O1	−179.0 (3)
C7—C1—C2—C3	178.3 (3)	C9—C10—C11—C12	0.6 (5)
C1—C2—C3—C4	0.5 (5)	O1—C10—C11—C12	179.8 (3)
C13—O2—C4—C3	173.2 (3)	C10—C11—C12—C7	−0.3 (6)
C13—O2—C4—C5	−5.6 (5)	C8—C7—C12—C11	−0.8 (5)
C2—C3—C4—O2	−178.1 (3)	C1—C7—C12—C11	178.8 (3)
C2—C3—C4—C5	0.8 (5)	C4—O2—C13—C14	−169.0 (3)
O2—C4—C5—C6	177.1 (3)	O2—C13—C14—C15	−176.1 (3)
C3—C4—C5—C6	−1.7 (5)	C13—C14—C15—C16	179.1 (3)
C4—C5—C6—C1	1.2 (5)	C14—C15—C16—C17	179.3 (3)
C2—C1—C6—C5	0.2 (5)	C15—C16—C17—C18	179.4 (3)
C7—C1—C6—C5	−179.2 (3)	C16—C17—C18—C19	−179.9 (3)
C6—C1—C7—C12	−6.3 (4)	C17—C18—C19—C20	177.7 (2)
C2—C1—C7—C12	174.4 (3)	C18—C19—C20—C21	−178.3 (3)
C6—C1—C7—C8	173.2 (3)	C19—C20—C21—C22	178.9 (3)
C2—C1—C7—C8	−6.1 (4)	C23—O4—C22—O3	−0.9 (6)
C12—C7—C8—C9	1.6 (5)	C23—O4—C22—C21	179.6 (4)
C1—C7—C8—C9	−178.0 (3)	C20—C21—C22—O3	−0.8 (6)
C7—C8—C9—C10	−1.4 (6)	C20—C21—C22—O4	178.8 (3)
C8—C9—C10—C11	0.2 (6)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of rings C1–C6 and C7–C12, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.89 (4)	1.96 (4)	2.813 (5)	162 (4)
C23—H23C···O1^ii	0.98	2.46	3.149 (5)	127
C23—H23A···O3^iii	0.98	2.74	3.564 (6)	142
C3—H3···O2^iv	0.95	2.82	3.627 (4)	143
C2—H2···Cg1^iv	0.95	2.98	3.737 (4)	138
C9—H9···Cg1^iv	0.95	2.89	3.716 (4)	146
C5—H5···Cg2^v	0.95	2.95	3.722 (4)	139
C12—H12···Cg2^v	0.95	2.83	3.661 (4)	147

Symmetry codes: (i) x+1/2, −y+1/2, z−3/2; (ii) x−1/2, −y+1/2, z+5/2; (iii) x, −y, z+1/2; (iv) x, −y, z−1/2; (v) x, −y+1, z+1/2.