3,5-Di-tert-butyl-2-hydroxy­benzoic acid

The title compound, C₁₅H₂₂O₃, is a charge-control agent used in electrophotography. There are two independent mol­ecules A and B in the asymmetric unit. The mol­ecules form centrosymmetric dimers A–A and B–B via pairs of O—H...O hydrogen bonds between the carboxyl groups.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.104
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.90

Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           68.25
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               4803
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5350
           Completeness (_total/calc)             89.78%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.90

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.688     0.939
            Tmin' and Tmax expected:      0.820     0.939
            RR' =      0.839
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.83
PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Expl ....       P -1
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O6     -   H7       =       1.07 Ang.

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 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
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEP-III (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.

(I)

Crystal data

C15H22O3	Z = 4
Mr = 250.34	F(000) = 544.0
Triclinic, P1	Dx = 1.140 Mg m^−3
Hall symbol: P -1	Cu Kα radiation, λ = 1.5418 Å
a = 9.597 (2) Å	Cell parameters from 1379 reflections
b = 9.828 (2) Å	θ = 6.9–65.2°
c = 17.783 (3) Å	µ = 0.63 mm^−1
α = 74.16 (1)°	T = 93 K
β = 78.85 (1)°	Block, colorless
γ = 65.11 (1)°	0.30 × 0.10 × 0.10 mm
V = 1457.9 (5) Å^3

Data collection

Rigaku R-AXIS RAPID Imaging Plate diffractometer	3053 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.037
48 frames, delta ω = 15 deg scans	θmax = 68.3°
Absorption correction: multi-scan (ABscor; Higashi, 1995)	h = −11→11
Tmin = 0.688, Tmax = 0.939	k = −11→11
13032 measured reflections	l = −21→20
4803 independent reflections

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.05(Max(Fo^2,0) + 2Fc^2)/3)^2]
wR(F^2) = 0.104	(Δ/σ)max = 0.050
S = 0.95	Δρmax = 0.33 e Å^−3
4766 reflections	Δρmin = −0.20 e Å^−3
337 parameters

Special details

Refinement. Refinement using reflections with F² > -3.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	0.4572 (1)	0.1777 (2)	0.00417 (8)	0.0358 (4)
O2	0.3077 (2)	0.0455 (2)	0.05222 (8)	0.0368 (4)
O3	0.3638 (2)	0.4535 (2)	0.02968 (8)	0.0348 (4)
O4	0.1728 (1)	0.8709 (2)	0.50130 (8)	0.0374 (4)
O5	0.0898 (2)	1.0827 (2)	0.54981 (9)	0.0430 (5)
O6	0.4470 (2)	0.6653 (2)	0.52306 (8)	0.0392 (4)
C1	0.2202 (2)	0.2925 (2)	0.0791 (1)	0.0278 (5)
C2	0.2388 (2)	0.4301 (2)	0.0709 (1)	0.0283 (5)
C3	0.1259 (2)	0.5498 (2)	0.1069 (1)	0.0269 (5)
C4	0.0032 (2)	0.5196 (2)	0.1513 (1)	0.0288 (5)
C5	−0.0173 (2)	0.3820 (2)	0.1622 (1)	0.0276 (5)
C6	0.0925 (2)	0.2703 (2)	0.1252 (1)	0.0284 (5)
C7	0.3366 (2)	0.1700 (2)	0.0423 (1)	0.0305 (6)
C8	0.1433 (2)	0.7024 (2)	0.0982 (1)	0.0302 (6)
C9	0.1495 (2)	0.7827 (2)	0.0110 (1)	0.0358 (6)
C10	0.2905 (2)	0.6709 (2)	0.1337 (1)	0.0359 (6)
C11	0.0071 (2)	0.8142 (2)	0.1409 (1)	0.0383 (6)
C12	−0.1571 (2)	0.3616 (2)	0.2149 (1)	0.0305 (6)
C13	−0.1562 (2)	0.3814 (2)	0.2975 (1)	0.0354 (6)
C14	−0.3053 (2)	0.4836 (3)	0.1784 (1)	0.0405 (6)
C15	−0.1566 (2)	0.2032 (3)	0.2216 (1)	0.0398 (7)
C16	0.3429 (2)	0.8994 (2)	0.5720 (1)	0.0302 (6)
C17	0.4616 (2)	0.7555 (2)	0.5647 (1)	0.0286 (5)
C18	0.5985 (2)	0.7002 (2)	0.6019 (1)	0.0278 (5)
C19	0.6069 (2)	0.7944 (2)	0.6456 (1)	0.0300 (6)
C20	0.4920 (2)	0.9385 (2)	0.6541 (1)	0.0285 (5)
C21	0.3607 (2)	0.9890 (2)	0.6160 (1)	0.0312 (6)
C22	0.1974 (2)	0.9495 (2)	0.5377 (1)	0.0322 (6)
C23	0.7294 (2)	0.5428 (2)	0.5952 (1)	0.0293 (5)
C24	0.6712 (2)	0.4137 (2)	0.6310 (1)	0.0346 (6)
C25	0.7865 (2)	0.5395 (2)	0.5085 (1)	0.0344 (6)
C26	0.8669 (2)	0.5100 (2)	0.6385 (1)	0.0336 (6)
C27	0.5075 (2)	1.0273 (2)	0.7089 (1)	0.0307 (6)
C28	0.6744 (2)	1.0107 (3)	0.7058 (1)	0.0405 (7)
C29	0.4061 (3)	1.1990 (3)	0.6871 (1)	0.0436 (7)
C30	0.4562 (3)	0.9628 (3)	0.7935 (1)	0.0433 (7)
H1	0.0812	0.1764	0.1310	0.0340*
H2	−0.0725	0.5973	0.1764	0.0347*
H3	0.424 (3)	0.364 (3)	0.012 (1)	0.0541*
H4	0.392 (3)	−0.034 (3)	0.030 (1)	0.0541*
H5	0.2808	1.0861	0.6197	0.0377*
H6	0.6974	0.7585	0.6718	0.0361*
H7	0.334 (3)	0.735 (3)	0.505 (1)	0.0541*
H8	−0.002 (3)	1.100 (2)	0.533 (1)	0.0541*
H9	−0.0857	0.8379	0.1193	0.0461*
H10	−0.0006	0.7681	0.1952	0.0461*
H11	0.0230	0.9059	0.1348	0.0461*
H12	−0.1563	0.4796	0.2942	0.0425*
H13	0.0554	0.8065	−0.0094	0.0432*
H14	0.1639	0.8749	0.0058	0.0432*
H15	0.2327	0.7167	−0.0175	0.0432*
H16	0.2821	0.6274	0.1883	0.0434*
H17	0.3035	0.7645	0.1263	0.0434*
H18	0.3770	0.6013	0.1086	0.0434*
H19	−0.2451	0.1950	0.2540	0.0477*
H20	−0.0662	0.1265	0.2442	0.0477*
H21	−0.1584	0.1902	0.1709	0.0477*
H22	−0.3070	0.4686	0.1282	0.0488*
H23	−0.3927	0.4740	0.2114	0.0488*
H24	−0.3074	0.5831	0.1735	0.0488*
H25	−0.2456	0.3733	0.3291	0.0425*
H26	−0.0667	0.3039	0.3205	0.0425*
H27	0.7395	0.9050	0.7191	0.0488*
H28	0.7062	1.0541	0.6543	0.0488*
H29	0.6811	1.0627	0.7420	0.0488*
H30	0.4397	1.2415	0.6358	0.0525*
H31	0.4142	1.2499	0.7236	0.0525*
H32	0.3018	1.2122	0.6886	0.0525*
H33	0.5212	0.8574	0.8086	0.0525*
H34	0.3526	0.9726	0.7963	0.0525*
H35	0.4630	1.0184	0.8277	0.0525*
H36	0.7512	0.3180	0.6246	0.0416*
H37	0.5852	0.4313	0.6053	0.0416*
H38	0.6413	0.4113	0.6853	0.0416*
H39	0.8637	0.4409	0.5048	0.0414*
H40	0.7027	0.5600	0.4804	0.0414*
H41	0.8286	0.6151	0.4868	0.0414*
H42	0.9457	0.4136	0.6323	0.0406*
H43	0.8351	0.5075	0.6927	0.0406*
H44	0.9056	0.5885	0.6174	0.0406*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0296 (8)	0.0322 (8)	0.0412 (9)	−0.0111 (7)	0.0101 (6)	−0.0118 (7)
O2	0.0314 (8)	0.0285 (8)	0.0496 (9)	−0.0108 (7)	0.0101 (7)	−0.0181 (7)
O3	0.0298 (8)	0.0328 (9)	0.0392 (9)	−0.0134 (7)	0.0086 (6)	−0.0099 (7)
O4	0.0286 (8)	0.0448 (9)	0.0415 (9)	−0.0078 (7)	−0.0064 (6)	−0.0219 (7)
O5	0.0280 (8)	0.0444 (10)	0.056 (1)	−0.0041 (8)	−0.0120 (7)	−0.0206 (8)
O6	0.0311 (8)	0.0458 (10)	0.0433 (9)	−0.0098 (7)	−0.0051 (7)	−0.0209 (8)
C1	0.026 (1)	0.027 (1)	0.028 (1)	−0.0081 (9)	0.0021 (8)	−0.0082 (9)
C2	0.0226 (10)	0.032 (1)	0.026 (1)	−0.0086 (9)	−0.0008 (8)	−0.0044 (9)
C3	0.0251 (10)	0.027 (1)	0.026 (1)	−0.0068 (9)	−0.0015 (8)	−0.0060 (9)
C4	0.0235 (10)	0.029 (1)	0.030 (1)	−0.0051 (9)	−0.0020 (8)	−0.0100 (9)
C5	0.0225 (10)	0.031 (1)	0.028 (1)	−0.0079 (9)	−0.0013 (8)	−0.0097 (9)
C6	0.026 (1)	0.030 (1)	0.029 (1)	−0.0110 (9)	−0.0023 (8)	−0.0072 (9)
C7	0.028 (1)	0.029 (1)	0.031 (1)	−0.0071 (9)	−0.0019 (9)	−0.0069 (10)
C8	0.032 (1)	0.028 (1)	0.030 (1)	−0.0115 (9)	0.0005 (9)	−0.0082 (9)
C9	0.040 (1)	0.033 (1)	0.034 (1)	−0.015 (1)	−0.0039 (9)	−0.0037 (10)
C10	0.042 (1)	0.040 (1)	0.029 (1)	−0.021 (1)	−0.0009 (9)	−0.0057 (10)
C11	0.043 (1)	0.030 (1)	0.042 (1)	−0.015 (1)	0.005 (1)	−0.012 (1)
C12	0.0243 (10)	0.037 (1)	0.033 (1)	−0.0142 (9)	0.0040 (8)	−0.0126 (10)
C13	0.032 (1)	0.042 (1)	0.035 (1)	−0.017 (1)	0.0040 (9)	−0.014 (1)
C14	0.026 (1)	0.057 (2)	0.039 (1)	−0.016 (1)	0.0032 (9)	−0.015 (1)
C15	0.037 (1)	0.052 (1)	0.040 (1)	−0.027 (1)	0.0118 (10)	−0.021 (1)
C16	0.025 (1)	0.034 (1)	0.030 (1)	−0.0097 (9)	−0.0002 (8)	−0.0087 (9)
C17	0.027 (1)	0.034 (1)	0.028 (1)	−0.0123 (9)	0.0012 (8)	−0.0123 (10)
C18	0.0241 (10)	0.033 (1)	0.026 (1)	−0.0111 (9)	−0.0013 (8)	−0.0065 (9)
C19	0.025 (1)	0.038 (1)	0.028 (1)	−0.0131 (10)	−0.0018 (8)	−0.0065 (10)
C20	0.0256 (10)	0.031 (1)	0.028 (1)	−0.0118 (9)	−0.0010 (8)	−0.0051 (9)
C21	0.029 (1)	0.032 (1)	0.033 (1)	−0.0105 (9)	−0.0010 (9)	−0.0097 (10)
C22	0.024 (1)	0.038 (1)	0.031 (1)	−0.0068 (10)	−0.0023 (9)	−0.012 (1)
C23	0.0250 (10)	0.032 (1)	0.031 (1)	−0.0084 (9)	−0.0035 (8)	−0.0095 (9)
C24	0.037 (1)	0.036 (1)	0.032 (1)	−0.015 (1)	−0.0015 (9)	−0.0103 (10)
C25	0.025 (1)	0.041 (1)	0.035 (1)	−0.0088 (10)	−0.0006 (9)	−0.011 (1)
C26	0.028 (1)	0.036 (1)	0.034 (1)	−0.0097 (9)	−0.0036 (9)	−0.0084 (10)
C27	0.030 (1)	0.034 (1)	0.031 (1)	−0.0114 (9)	−0.0037 (9)	−0.0107 (10)
C28	0.039 (1)	0.046 (1)	0.045 (1)	−0.019 (1)	−0.004 (1)	−0.018 (1)
C29	0.048 (1)	0.039 (1)	0.049 (1)	−0.015 (1)	−0.013 (1)	−0.016 (1)
C30	0.050 (1)	0.055 (2)	0.036 (1)	−0.028 (1)	0.000 (1)	−0.017 (1)

Geometric parameters (Å, º)

O1—C7	1.243 (2)	C14—H23	0.951
O2—C7	1.324 (2)	C14—H24	0.949
O2—H4	0.97 (2)	C15—H19	0.950
O3—C2	1.353 (2)	C15—H20	0.949
O3—H3	0.93 (2)	C15—H21	0.949
O4—C22	1.248 (2)	C16—C17	1.415 (3)
O5—C22	1.325 (2)	C16—C21	1.403 (3)
O5—H8	0.92 (2)	C16—C22	1.466 (3)
O6—C17	1.364 (2)	C17—C18	1.413 (3)
O6—H7	1.07 (2)	C18—C19	1.396 (3)
C1—C2	1.402 (3)	C18—C23	1.547 (3)
C1—C6	1.400 (3)	C19—C20	1.407 (3)
C1—C7	1.464 (3)	C19—H6	0.951
C2—C3	1.428 (3)	C20—C21	1.383 (3)
C3—C4	1.380 (3)	C20—C27	1.538 (3)
C3—C8	1.541 (3)	C21—H5	0.950
C4—C5	1.404 (3)	C23—C24	1.532 (3)
C4—H2	0.950	C23—C25	1.537 (3)
C5—C6	1.379 (3)	C23—C26	1.530 (3)
C5—C12	1.535 (3)	C24—H36	0.951
C6—H1	0.950	C24—H37	0.950
C8—C9	1.539 (3)	C24—H38	0.949
C8—C10	1.537 (3)	C25—H39	0.951
C8—C11	1.535 (3)	C25—H40	0.950
C9—H13	0.951	C25—H41	0.949
C9—H14	0.950	C26—H42	0.951
C9—H15	0.950	C26—H43	0.949
C10—H16	0.950	C26—H44	0.950
C10—H17	0.950	C27—C28	1.531 (3)
C10—H18	0.950	C27—C29	1.534 (3)
C11—H9	0.950	C27—C30	1.537 (3)
C11—H10	0.951	C28—H27	0.950
C11—H11	0.950	C28—H28	0.950
C12—C13	1.535 (3)	C28—H29	0.950
C12—C14	1.542 (3)	C29—H30	0.950
C12—C15	1.527 (3)	C29—H31	0.951
C13—H12	0.951	C29—H32	0.949
C13—H25	0.951	C30—H33	0.950
C13—H26	0.950	C30—H34	0.951
C14—H22	0.949	C30—H35	0.949
C7—O2—H4	111 (1)	H19—C15—H21	109.6
C2—O3—H3	105 (1)	H20—C15—H21	109.6
C22—O5—H8	110 (1)	C17—C16—C21	120.1 (2)
C17—O6—H7	99 (1)	C17—C16—C22	119.6 (2)
C2—C1—C6	119.7 (2)	C21—C16—C22	120.2 (2)
C2—C1—C7	120.3 (2)	O6—C17—C16	121.4 (2)
C6—C1—C7	120.0 (2)	O6—C17—C18	118.1 (2)
O3—C2—C1	121.6 (2)	C16—C17—C18	120.5 (2)
O3—C2—C3	117.8 (2)	C17—C18—C19	116.1 (2)
C1—C2—C3	120.6 (2)	C17—C18—C23	121.4 (2)
C2—C3—C4	116.3 (2)	C19—C18—C23	122.5 (2)
C2—C3—C8	121.5 (2)	C18—C19—C20	125.2 (2)
C4—C3—C8	122.1 (2)	C18—C19—H6	117.4
C3—C4—C5	124.6 (2)	C20—C19—H6	117.4
C3—C4—H2	117.7	C19—C20—C21	116.7 (2)
C5—C4—H2	117.7	C19—C20—C27	120.9 (2)
C4—C5—C6	117.4 (2)	C21—C20—C27	122.2 (2)
C4—C5—C12	119.3 (2)	C16—C21—C20	121.3 (2)
C6—C5—C12	123.4 (2)	C16—C21—H5	119.3
C1—C6—C5	121.4 (2)	C20—C21—H5	119.3
C1—C6—H1	119.3	O4—C22—O5	121.2 (2)
C5—C6—H1	119.3	O4—C22—C16	122.9 (2)
O1—C7—O2	120.4 (2)	O5—C22—C16	115.9 (2)
O1—C7—C1	123.7 (2)	C18—C23—C24	110.2 (2)
O2—C7—C1	115.9 (2)	C18—C23—C25	110.1 (2)
C3—C8—C9	109.9 (2)	C18—C23—C26	111.7 (2)
C3—C8—C10	109.5 (2)	C24—C23—C25	109.1 (2)
C3—C8—C11	112.2 (2)	C24—C23—C26	107.6 (2)
C9—C8—C10	110.4 (2)	C25—C23—C26	108.1 (2)
C9—C8—C11	107.1 (2)	C23—C24—H36	109.4
C10—C8—C11	107.5 (2)	C23—C24—H37	109.5
C8—C9—H13	109.5	C23—C24—H38	109.5
C8—C9—H14	109.5	H36—C24—H37	109.4
C8—C9—H15	109.6	H36—C24—H38	109.5
H13—C9—H14	109.4	H37—C24—H38	109.6
H13—C9—H15	109.4	C23—C25—H39	109.5
H14—C9—H15	109.5	C23—C25—H40	109.5
C8—C10—H16	109.4	C23—C25—H41	109.5
C8—C10—H17	109.5	H39—C25—H40	109.4
C8—C10—H18	109.5	H39—C25—H41	109.4
H16—C10—H17	109.5	H40—C25—H41	109.5
H16—C10—H18	109.5	C23—C26—H42	109.4
H17—C10—H18	109.5	C23—C26—H43	109.5
C8—C11—H9	109.6	C23—C26—H44	109.4
C8—C11—H10	109.5	H42—C26—H43	109.5
C8—C11—H11	109.6	H42—C26—H44	109.4
H9—C11—H10	109.4	H43—C26—H44	109.5
H9—C11—H11	109.5	C20—C27—C28	111.5 (2)
H10—C11—H11	109.4	C20—C27—C29	111.4 (2)
C5—C12—C13	110.0 (2)	C20—C27—C30	108.7 (2)
C5—C12—C14	108.6 (2)	C28—C27—C29	108.0 (2)
C5—C12—C15	111.5 (2)	C28—C27—C30	108.6 (2)
C13—C12—C14	109.8 (2)	C29—C27—C30	108.6 (2)
C13—C12—C15	108.7 (2)	C27—C28—H27	109.5
C14—C12—C15	108.2 (2)	C27—C28—H28	109.5
C12—C13—H12	109.6	C27—C28—H29	109.5
C12—C13—H25	109.5	H27—C28—H28	109.5
C12—C13—H26	109.6	H27—C28—H29	109.5
H12—C13—H25	109.3	H28—C28—H29	109.4
H12—C13—H26	109.4	C27—C29—H30	109.5
H25—C13—H26	109.4	C27—C29—H31	109.4
C12—C14—H22	109.5	C27—C29—H32	109.6
C12—C14—H23	109.3	H30—C29—H31	109.4
C12—C14—H24	109.4	H30—C29—H32	109.5
H22—C14—H23	109.5	H31—C29—H32	109.4
H22—C14—H24	109.6	C27—C30—H33	109.4
H23—C14—H24	109.5	C27—C30—H34	109.4
C12—C15—H19	109.3	C27—C30—H35	109.5
C12—C15—H20	109.4	H33—C30—H34	109.4
C12—C15—H21	109.4	H33—C30—H35	109.6
H19—C15—H20	109.5	H34—C30—H35	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.93 (2)	1.76 (2)	2.613 (2)	151 (2)
O6—H7···O4	1.07 (2)	1.56 (2)	2.579 (2)	158 (2)
O2—H4···O1^i	0.97 (2)	1.69 (2)	2.659 (2)	177 (2)
O5—H8···O4^ii	0.92 (2)	1.74 (2)	2.661 (2)	179 (2)

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