1,4-Bis(3,5-di-tert-butyl-2-hydroxy­benzyl­idene­amino­methyl)­benzene

The title compound, C₃₈H₅₂N₂O₂, has been obtained by a Schiff base reaction of 3,5-di-tert-butyl­salic­aldehyde and p-xyl­enedi­amine in methanol. The mol­ecule is located on a crystallographic inversion centre, and the hydrogen bonding is exclusively intramolecular.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.047
• wR factor = 0.115
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.850     1.000
            Tmin' and Tmax expected:      0.975     0.994
            RR' =      0.867
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    -   C18     ..       5.35 su

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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: COLLECT (Nonius, 2002); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

1,4-Bis(3,5-di-tert-butyl-2-hydroxybenzylideneaminomethyl)benzene

Crystal data

C38H52N2O2	F(000) = 620
Mr = 568.82	Accurate unit cell determined from phi-chi data using DIRAX (Duisenberg, 1992).
Monoclinic, P21/c	Dx = 1.138 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.8792 (18) Å	Cell parameters from 46 reflections
b = 10.4601 (11) Å	θ = 5.5–20.5°
c = 10.4395 (15) Å	µ = 0.07 mm^−1
β = 106.856 (10)°	T = 150 K
V = 1659.5 (4) Å^3	Block, yellow
Z = 2	0.36 × 0.25 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	3791 independent reflections
Radiation source: Rotating anode	2661 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Wide–angle φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −20→20
Tmin = 0.850, Tmax = 1.000	k = −13→13
43559 measured reflections	l = −13→13

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 0.5767P] where P = (Fo^2 + 2Fc^2)/3
3791 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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
O30	0.14240 (7)	−0.00435 (10)	0.50563 (11)	0.0302 (3)
N20	0.08326 (8)	0.16781 (12)	0.32842 (11)	0.0256 (4)
C1	−0.05226 (10)	0.10706 (15)	−0.02303 (14)	0.0288 (5)
C2	0.01496 (9)	0.09803 (14)	0.09648 (14)	0.0238 (4)
C3	0.06685 (10)	−0.01058 (15)	0.11775 (14)	0.0287 (5)
C4	0.02961 (10)	0.20704 (15)	0.19587 (14)	0.0264 (5)
C5	0.13754 (9)	0.24683 (14)	0.40117 (14)	0.0233 (4)
C6	0.19586 (9)	0.21098 (14)	0.53204 (14)	0.0214 (4)
C7	0.25310 (9)	0.30177 (14)	0.60838 (14)	0.0220 (4)
C8	0.31309 (9)	0.27112 (13)	0.72957 (14)	0.0206 (4)
C9	0.31548 (9)	0.14393 (14)	0.77053 (13)	0.0215 (4)
C10	0.26079 (9)	0.04827 (13)	0.69890 (13)	0.0210 (4)
C11	0.19869 (9)	0.08399 (14)	0.57852 (13)	0.0218 (4)
C12	0.26954 (10)	−0.09143 (14)	0.74628 (14)	0.0247 (4)
C13	0.34254 (11)	−0.10899 (15)	0.87761 (15)	0.0312 (5)
C14	0.18354 (11)	−0.13670 (16)	0.77040 (16)	0.0337 (5)
C15	0.29201 (12)	−0.17506 (15)	0.63962 (16)	0.0344 (5)
C16	0.37666 (10)	0.37241 (14)	0.81026 (14)	0.0234 (4)
C17	0.42833 (12)	0.32403 (17)	0.94876 (16)	0.0405 (6)
C18	0.32464 (12)	0.48989 (16)	0.83023 (18)	0.0382 (6)
C19	0.44122 (11)	0.41042 (18)	0.73364 (16)	0.0388 (6)
H1	−0.08880	0.18070	−0.04000	0.0350*
H3	0.11320	−0.01910	0.19860	0.0340*
H4A	0.05910	0.27850	0.16380	0.0320*
H4B	−0.02800	0.23830	0.20180	0.0320*
H5	0.14010	0.33140	0.36940	0.0280*
H7	0.25080	0.38710	0.57630	0.0260*
H9	0.35720	0.12110	0.85270	0.0260*
H13A	0.39860	−0.08000	0.86620	0.0470*
H13B	0.34700	−0.19960	0.90270	0.0470*
H13C	0.32880	−0.05870	0.94820	0.0470*
H14A	0.17270	−0.08750	0.84400	0.0510*
H14B	0.18820	−0.22770	0.79370	0.0510*
H14C	0.13470	−0.12380	0.68890	0.0510*
H15A	0.24480	−0.16850	0.55520	0.0520*
H15B	0.29820	−0.26430	0.66960	0.0520*
H15C	0.34740	−0.14570	0.62600	0.0520*
H17A	0.46530	0.25170	0.93930	0.0610*
H17B	0.38720	0.29630	0.99750	0.0610*
H17C	0.46560	0.39290	0.99840	0.0610*
H18A	0.36530	0.55510	0.88030	0.0570*
H18B	0.28360	0.46560	0.88040	0.0570*
H18C	0.29160	0.52430	0.74280	0.0570*
H19A	0.48120	0.47640	0.78370	0.0580*
H19B	0.40860	0.44390	0.64550	0.0580*
H19C	0.47540	0.33540	0.72240	0.0580*
H30	0.1066 (14)	0.042 (2)	0.427 (2)	0.065 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O30	0.0344 (6)	0.0244 (6)	0.0260 (6)	−0.0102 (5)	−0.0002 (5)	−0.0028 (5)
N20	0.0239 (7)	0.0305 (7)	0.0204 (6)	−0.0036 (5)	0.0033 (5)	−0.0009 (5)
C1	0.0264 (8)	0.0319 (9)	0.0244 (8)	0.0031 (7)	0.0017 (6)	0.0026 (7)
C2	0.0197 (7)	0.0310 (8)	0.0197 (7)	−0.0045 (6)	0.0042 (6)	0.0019 (6)
C3	0.0224 (8)	0.0379 (9)	0.0199 (7)	0.0020 (7)	−0.0031 (6)	0.0016 (7)
C4	0.0227 (8)	0.0304 (8)	0.0234 (8)	−0.0010 (6)	0.0024 (6)	0.0016 (6)
C5	0.0228 (7)	0.0235 (7)	0.0240 (7)	0.0004 (6)	0.0076 (6)	0.0001 (6)
C6	0.0198 (7)	0.0241 (7)	0.0206 (7)	−0.0006 (6)	0.0062 (6)	−0.0012 (6)
C7	0.0248 (8)	0.0183 (7)	0.0233 (7)	−0.0010 (6)	0.0074 (6)	−0.0003 (6)
C8	0.0215 (7)	0.0202 (7)	0.0202 (7)	−0.0019 (6)	0.0064 (6)	−0.0016 (6)
C9	0.0223 (7)	0.0226 (7)	0.0187 (7)	0.0001 (6)	0.0047 (6)	−0.0002 (6)
C10	0.0243 (7)	0.0196 (7)	0.0208 (7)	−0.0012 (6)	0.0094 (6)	−0.0014 (6)
C11	0.0229 (7)	0.0230 (7)	0.0201 (7)	−0.0054 (6)	0.0074 (6)	−0.0053 (6)
C12	0.0326 (8)	0.0181 (7)	0.0239 (7)	−0.0035 (6)	0.0092 (6)	−0.0012 (6)
C13	0.0412 (9)	0.0225 (8)	0.0287 (8)	0.0009 (7)	0.0083 (7)	0.0054 (6)
C14	0.0400 (10)	0.0289 (9)	0.0337 (9)	−0.0106 (7)	0.0129 (7)	0.0004 (7)
C15	0.0522 (11)	0.0214 (8)	0.0315 (9)	0.0022 (7)	0.0153 (8)	−0.0005 (7)
C16	0.0272 (8)	0.0204 (7)	0.0200 (7)	−0.0059 (6)	0.0027 (6)	−0.0016 (6)
C17	0.0480 (11)	0.0340 (9)	0.0279 (9)	−0.0163 (8)	−0.0074 (8)	0.0013 (7)
C18	0.0417 (10)	0.0271 (9)	0.0444 (10)	−0.0083 (7)	0.0101 (8)	−0.0120 (8)
C19	0.0359 (9)	0.0484 (11)	0.0316 (9)	−0.0195 (8)	0.0092 (7)	−0.0095 (8)

Geometric parameters (Å, º)

O30—C11	1.3555 (18)	C3—H3	0.9500
O30—H30	0.98 (2)	C4—H4A	0.9900
N20—C5	1.2741 (19)	C4—H4B	0.9900
N20—C4	1.4578 (18)	C5—H5	0.9500
C1—C2	1.390 (2)	C7—H7	0.9500
C1—C3^i	1.385 (2)	C9—H9	0.9500
C2—C3	1.383 (2)	C13—H13A	0.9800
C2—C4	1.514 (2)	C13—H13B	0.9800
C5—C6	1.460 (2)	C13—H13C	0.9800
C6—C11	1.410 (2)	C14—H14A	0.9800
C6—C7	1.394 (2)	C14—H14B	0.9800
C7—C8	1.383 (2)	C14—H14C	0.9800
C8—C9	1.395 (2)	C15—H15A	0.9800
C8—C16	1.536 (2)	C15—H15B	0.9800
C9—C10	1.392 (2)	C15—H15C	0.9800
C10—C11	1.4045 (19)	C17—H17A	0.9800
C10—C12	1.536 (2)	C17—H17B	0.9800
C12—C14	1.534 (2)	C17—H17C	0.9800
C12—C15	1.537 (2)	C18—H18A	0.9800
C12—C13	1.528 (2)	C18—H18B	0.9800
C16—C18	1.528 (2)	C18—H18C	0.9800
C16—C19	1.525 (2)	C19—H19A	0.9800
C16—C17	1.527 (2)	C19—H19B	0.9800
C1—H1	0.9500	C19—H19C	0.9800
O30···N20	2.5573 (16)	H13A···C9	2.7300
O30···C14	2.989 (2)	H13A···H9	2.2000
O30···C15	2.977 (2)	H13A···H15C	2.5000
O30···H14C	2.3200	H13A···C19^ix	3.0200
O30···H15A	2.3200	H13A···H19C^ix	2.5900
N20···O30	2.5573 (16)	H13B···H14B	2.4600
N20···H3	2.5000	H13B···H15B	2.4300
N20···H30	1.65 (2)	H13C···C9	2.7800
C2···C5^ii	3.589 (2)	H13C···H9	2.2300
C4···C14^iii	3.579 (2)	H13C···H14A	2.4200
C5···C2^iv	3.589 (2)	H13C···H19B^iv	2.4000
C14···O30	2.989 (2)	H14A···H13C	2.4200
C14···C4^iii	3.579 (2)	H14A···C1^iii	3.0400
C15···O30	2.977 (2)	H14B···H13B	2.4600
C1···H14A^iii	3.0400	H14B···H15B	2.4900
C4···H30	2.93 (2)	H14B···H4B^iii	2.5600
C5···H30	2.23 (2)	H14C···O30	2.3200
C6···H18B^ii	3.0200	H14C···C11	2.7900
C6···H4A^iv	2.8900	H14C···H15A	2.5800
C7···H19B	2.8100	H14C···H1^v	2.5400
C7···H18C	2.7000	H14C···H4B^iii	2.5900
C7···H17B^ii	2.8900	H15A···O30	2.3200
C8···H17B^ii	3.0700	H15A···C11	2.7700
C9···H13A	2.7300	H15A···H14C	2.5800
C9···H13C	2.7800	H15B···C18^x	3.0300
C9···H17B	2.8100	H15B···H13B	2.4300
C9···H17A	2.7600	H15B···H14B	2.4900
C11···H15A	2.7700	H15B···H18C^x	2.3500
C11···H18B^ii	2.8300	H15C···H13A	2.5000
C11···H14C	2.7900	H17A···C9	2.7600
C11···H4A^iv	2.9900	H17A···H9	2.1700
C13···H9	2.4400	H17A···H19C	2.4800
C14···H4B^iii	2.7800	H17B···C9	2.8100
C14···H1^v	3.1000	H17B···H9	2.3400
C17···H9	2.4800	H17B···H18B	2.4800
C18···H7	2.7800	H17B···C7^iv	2.8900
C18···H15B^vi	3.0300	H17B···C8^iv	3.0700
C19···H7	3.0000	H17C···H18A	2.4100
C19···H13A^vii	3.0200	H17C···H19A	2.4800
H1···H4B	2.5000	H17C···H17C^xi	2.4900
H1···C14^viii	3.1000	H17C···H19A^xi	2.5800
H1···H14C^viii	2.5400	H18A···H17C	2.4100
H3···N20	2.5000	H18A···H19A	2.4800
H3···H30	2.5000	H18B···H17B	2.4800
H4A···H5	2.2300	H18B···C6^iv	3.0200
H4A···C6^ii	2.8900	H18B···C11^iv	2.8300
H4A···C11^ii	2.9900	H18C···C7	2.7000
H4B···H1	2.5000	H18C···H7	2.2000
H4B···C14^iii	2.7800	H18C···H15B^vi	2.3500
H4B···H14B^iii	2.5600	H18C···H19B	2.5100
H4B···H14C^iii	2.5900	H19A···H17C	2.4800
H5···H4A	2.2300	H19A···H18A	2.4800
H5···H7	2.4300	H19A···H17C^xi	2.5800
H7···C18	2.7800	H19B···C7	2.8100
H7···C19	3.0000	H19B···H7	2.4700
H7···H5	2.4300	H19B···H18C	2.5100
H7···H18C	2.2000	H19B···H13C^ii	2.4000
H7···H19B	2.4700	H19C···H17A	2.4800
H9···C13	2.4400	H19C···H13A^vii	2.5900
H9···C17	2.4800	H30···N20	1.65 (2)
H9···H13A	2.2000	H30···C4	2.93 (2)
H9···H13C	2.2300	H30···C5	2.23 (2)
H9···H17A	2.1700	H30···H3	2.5000
H9···H17B	2.3400
C11—O30—H30	105.1 (12)	H4A—C4—H4B	108.00
C4—N20—C5	119.43 (13)	N20—C5—H5	119.00
C2—C1—C3^i	121.16 (14)	C6—C5—H5	119.00
C1—C2—C3	117.81 (13)	C6—C7—H7	119.00
C3—C2—C4	122.87 (13)	C8—C7—H7	119.00
C1—C2—C4	119.30 (13)	C8—C9—H9	118.00
C1^i—C3—C2	121.03 (14)	C10—C9—H9	118.00
N20—C4—C2	111.72 (12)	C12—C13—H13A	109.00
N20—C5—C6	121.81 (13)	C12—C13—H13B	109.00
C5—C6—C7	119.45 (13)	C12—C13—H13C	109.00
C7—C6—C11	119.64 (13)	H13A—C13—H13B	110.00
C5—C6—C11	120.81 (13)	H13A—C13—H13C	109.00
C6—C7—C8	121.81 (13)	H13B—C13—H13C	109.00
C7—C8—C16	120.72 (12)	C12—C14—H14A	109.00
C9—C8—C16	122.34 (12)	C12—C14—H14B	110.00
C7—C8—C9	116.87 (13)	C12—C14—H14C	109.00
C8—C9—C10	124.31 (13)	H14A—C14—H14B	109.00
C9—C10—C12	121.79 (12)	H14A—C14—H14C	109.00
C11—C10—C12	121.04 (12)	H14B—C14—H14C	109.00
C9—C10—C11	117.14 (13)	C12—C15—H15A	110.00
O30—C11—C10	119.90 (13)	C12—C15—H15B	109.00
C6—C11—C10	120.16 (13)	C12—C15—H15C	109.00
O30—C11—C6	119.92 (12)	H15A—C15—H15B	109.00
C10—C12—C13	112.18 (12)	H15A—C15—H15C	109.00
C10—C12—C14	110.18 (13)	H15B—C15—H15C	109.00
C13—C12—C14	107.19 (12)	C16—C17—H17A	109.00
C13—C12—C15	107.85 (13)	C16—C17—H17B	109.00
C10—C12—C15	109.05 (12)	C16—C17—H17C	109.00
C14—C12—C15	110.37 (13)	H17A—C17—H17B	109.00
C8—C16—C18	109.53 (13)	H17A—C17—H17C	109.00
C8—C16—C19	109.10 (12)	H17B—C17—H17C	110.00
C8—C16—C17	112.21 (13)	C16—C18—H18A	110.00
C17—C16—C19	108.95 (14)	C16—C18—H18B	109.00
C18—C16—C19	109.52 (13)	C16—C18—H18C	109.00
C17—C16—C18	107.49 (13)	H18A—C18—H18B	109.00
C2—C1—H1	119.00	H18A—C18—H18C	109.00
C3^i—C1—H1	119.00	H18B—C18—H18C	109.00
C2—C3—H3	119.00	C16—C19—H19A	110.00
C1^i—C3—H3	119.00	C16—C19—H19B	109.00
N20—C4—H4A	109.00	C16—C19—H19C	110.00
N20—C4—H4B	109.00	H19A—C19—H19B	109.00
C2—C4—H4A	109.00	H19A—C19—H19C	109.00
C2—C4—H4B	109.00	H19B—C19—H19C	109.00
C5—N20—C4—C2	144.47 (14)	C7—C8—C16—C18	52.91 (18)
C4—N20—C5—C6	−177.07 (13)	C7—C8—C9—C10	−1.2 (2)
C3^i—C1—C2—C3	0.0 (2)	C16—C8—C9—C10	−178.22 (14)
C3^i—C1—C2—C4	178.79 (14)	C7—C8—C16—C17	172.21 (14)
C2—C1—C3^i—C2^i	0.0 (2)	C9—C8—C16—C17	−10.9 (2)
C4—C2—C3—C1^i	−178.74 (15)	C9—C8—C16—C18	−130.22 (15)
C1—C2—C4—N20	163.11 (14)	C9—C8—C16—C19	109.92 (16)
C1—C2—C3—C1^i	0.0 (2)	C8—C9—C10—C12	177.16 (14)
C3—C2—C4—N20	−18.2 (2)	C8—C9—C10—C11	−0.9 (2)
N20—C5—C6—C11	4.7 (2)	C9—C10—C11—C6	2.5 (2)
N20—C5—C6—C7	−179.07 (14)	C12—C10—C11—O30	3.3 (2)
C5—C6—C11—O30	−4.7 (2)	C9—C10—C11—O30	−178.69 (13)
C5—C6—C11—C10	174.11 (14)	C11—C10—C12—C14	−62.09 (17)
C7—C6—C11—O30	179.11 (13)	C11—C10—C12—C15	59.18 (19)
C7—C6—C11—C10	−2.1 (2)	C12—C10—C11—C6	−175.52 (13)
C5—C6—C7—C8	−176.36 (14)	C9—C10—C12—C13	0.7 (2)
C11—C6—C7—C8	−0.1 (2)	C9—C10—C12—C14	119.97 (15)
C6—C7—C8—C16	178.75 (14)	C9—C10—C12—C15	−118.76 (15)
C6—C7—C8—C9	1.7 (2)	C11—C10—C12—C13	178.58 (14)
C7—C8—C16—C19	−66.96 (18)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O30—H30···N20	0.98 (2)	1.65 (2)	2.5573 (16)	152.9 (19)
C3—H3···N20	0.95	2.5	2.8380 (19)	101
C14—H14C···O30	0.98	2.32	2.989 (2)	125
C15—H15A···O30	0.98	2.32	2.977 (2)	124