2-((Z)-{3-[(Z)-(2-Hy-droxy-5-methyl-benzyl-idene)amino]-2,2-dimethyl-prop-yl}imino-meth-yl)-4-methyl-phenol.

In the title compound, C(21)H(26)N(2)O(2), the dihedral angle between the two benzene rings is 73.47 (16)°. Strong intra-molecular O-H⋯N hydrogen bonds generate S(6) ring motifs. The substituted benzene rings are twisted around the central quaternary C atom in opposite directions, making a vault geometry.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Kargar et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C21H26N2O2

M = 338.44

Orthorhombic,

a = 5.8950 (3) Å

b = 17.8634 (10) Å

c = 18.2140 (11) Å

V = 1918.02 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.30 × 0.18 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.978, T max = 0.991

16208 measured reflections

2199 independent reflections

1368 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.112

S = 1.03

2199 reflections

231 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051688/gw2096sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051688/gw2096Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H26N2O2	F(000) = 728
Mr = 338.44	Dx = 1.172 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2150 reflections
a = 5.8950 (3) Å	θ = 2.5–29.8°
b = 17.8634 (10) Å	µ = 0.08 mm−1
c = 18.2140 (11) Å	T = 296 K
V = 1918.02 (19) Å3	Plate, yellow
Z = 4	0.30 × 0.18 × 0.12 mm

Bruker SMART APEXII CCD area-detector diffractometer	2199 independent reflections
Radiation source: fine-focus sealed tube	1368 reflections with I > 2σ(I)
graphite	Rint = 0.062
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.978, Tmax = 0.991	k = −22→22
16208 measured reflections	l = −22→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0485P)2 + 0.082P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2199 reflections	Δρmax = 0.15 e Å−3
231 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

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.

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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
O1	0.4633 (4)	0.71477 (13)	0.18637 (14)	0.0691 (7)
H1A	0.3887	0.6786	0.1999	0.104*
O2	−0.1798 (4)	0.44857 (14)	0.02145 (14)	0.0769 (7)
H2A	−0.0936	0.4643	0.0533	0.115*
N1	0.1130 (4)	0.62471 (14)	0.19160 (15)	0.0576 (7)
N2	0.1758 (5)	0.44863 (14)	0.10671 (15)	0.0589 (7)
C1	0.3362 (5)	0.75772 (18)	0.14103 (17)	0.0513 (8)
C2	0.4215 (5)	0.82499 (18)	0.11644 (19)	0.0593 (9)
H2	0.5650	0.8401	0.1316	0.071*
C3	0.2994 (6)	0.87012 (19)	0.07010 (18)	0.0593 (9)
H3	0.3614	0.9153	0.0545	0.071*
C4	0.0828 (5)	0.84926 (18)	0.04596 (18)	0.0558 (9)
C5	−0.0004 (6)	0.78143 (17)	0.07017 (17)	0.0544 (8)
H5	−0.1421	0.7659	0.0537	0.065*
C6	0.1183 (5)	0.73540 (17)	0.11802 (17)	0.0487 (8)
C7	−0.0504 (7)	0.90009 (19)	−0.0039 (2)	0.0777 (11)
H7A	0.0048	0.8952	−0.0533	0.117*
H7B	−0.0332	0.9510	0.0120	0.117*
H7C	−0.2079	0.8865	−0.0023	0.117*
C8	0.0162 (6)	0.66623 (17)	0.14440 (18)	0.0562 (9)
H8	−0.1246	0.6520	0.1261	0.067*
C9	−0.0035 (6)	0.55714 (17)	0.21706 (19)	0.0641 (10)
H9A	−0.1067	0.5401	0.1791	0.077*
H9B	−0.0929	0.5693	0.2601	0.077*
C10	0.1605 (6)	0.49409 (17)	0.23599 (18)	0.0615 (9)
C11	0.3201 (7)	0.5184 (2)	0.2980 (2)	0.0892 (13)
H11A	0.2336	0.5276	0.3417	0.134*
H11B	0.3982	0.5633	0.2838	0.134*
H11C	0.4286	0.4794	0.3072	0.134*
C12	0.0218 (8)	0.4259 (2)	0.2593 (2)	0.0891 (13)
H12A	0.1216	0.3842	0.2673	0.134*
H12B	−0.0850	0.4136	0.2214	0.134*
H12C	−0.0582	0.4370	0.3039	0.134*
C13	0.3085 (6)	0.47518 (18)	0.16952 (19)	0.0640 (10)
H13A	0.3929	0.5194	0.1551	0.077*
H13B	0.4171	0.4369	0.1833	0.077*
C14	0.2562 (6)	0.39671 (18)	0.06619 (18)	0.0571 (9)
H14	0.3962	0.3762	0.0784	0.069*
C15	0.1397 (5)	0.36831 (16)	0.00220 (18)	0.0512 (8)
C16	0.2388 (6)	0.31298 (17)	−0.04090 (17)	0.0542 (8)
H16	0.3790	0.2940	−0.0267	0.065*
C17	0.1400 (6)	0.28490 (17)	−0.10341 (18)	0.0570 (9)
C18	−0.0714 (6)	0.3128 (2)	−0.1220 (2)	0.0638 (10)
H18	−0.1438	0.2943	−0.1636	0.077*
C19	−0.1782 (6)	0.3673 (2)	−0.08042 (19)	0.0648 (9)
H19	−0.3205	0.3850	−0.0941	0.078*
C20	−0.0727 (5)	0.39531 (18)	−0.01880 (19)	0.0542 (9)
C21	0.2588 (7)	0.22644 (19)	−0.14975 (19)	0.0775 (12)
H21A	0.3779	0.2497	−0.1775	0.116*
H21B	0.1517	0.2039	−0.1827	0.116*
H21C	0.3222	0.1886	−0.1184	0.116*

	U11	U22	U33	U12	U13	U23
O1	0.0584 (15)	0.0711 (17)	0.0778 (17)	0.0012 (12)	−0.0145 (14)	0.0031 (14)
O2	0.0690 (16)	0.0818 (17)	0.0798 (19)	0.0272 (15)	0.0009 (14)	−0.0003 (14)
N1	0.0590 (17)	0.0501 (16)	0.0636 (18)	0.0000 (13)	0.0014 (15)	−0.0032 (14)
N2	0.0615 (17)	0.0523 (17)	0.0629 (18)	0.0032 (14)	−0.0008 (16)	0.0023 (15)
C1	0.0439 (18)	0.0545 (19)	0.056 (2)	0.0055 (16)	−0.0042 (16)	−0.0062 (16)
C2	0.0503 (19)	0.060 (2)	0.068 (2)	−0.0066 (17)	−0.0024 (18)	−0.0138 (18)
C3	0.057 (2)	0.056 (2)	0.065 (2)	−0.0064 (17)	0.0018 (18)	−0.0047 (18)
C4	0.056 (2)	0.054 (2)	0.058 (2)	0.0018 (16)	0.0007 (17)	−0.0054 (16)
C5	0.0467 (18)	0.055 (2)	0.061 (2)	−0.0020 (16)	−0.0037 (17)	−0.0096 (17)
C6	0.0423 (17)	0.0497 (18)	0.0540 (19)	−0.0008 (14)	0.0011 (16)	−0.0062 (16)
C7	0.078 (3)	0.070 (2)	0.085 (3)	−0.0059 (19)	−0.015 (2)	0.014 (2)
C8	0.0485 (19)	0.057 (2)	0.063 (2)	−0.0020 (16)	0.0052 (17)	−0.0098 (17)
C9	0.067 (2)	0.061 (2)	0.064 (2)	−0.0107 (19)	0.0100 (19)	−0.0015 (17)
C10	0.072 (2)	0.052 (2)	0.060 (2)	−0.0139 (19)	−0.0039 (19)	0.0081 (17)
C11	0.109 (3)	0.080 (3)	0.079 (3)	−0.012 (2)	−0.027 (3)	−0.002 (2)
C12	0.116 (3)	0.077 (3)	0.074 (3)	−0.032 (3)	−0.009 (3)	0.016 (2)
C13	0.060 (2)	0.052 (2)	0.080 (3)	−0.0010 (17)	−0.006 (2)	−0.0061 (18)
C14	0.0495 (19)	0.054 (2)	0.068 (2)	0.0020 (16)	−0.0012 (18)	0.0062 (18)
C15	0.0506 (19)	0.0491 (18)	0.0538 (19)	0.0021 (15)	0.0049 (17)	0.0105 (16)
C16	0.0496 (19)	0.0534 (19)	0.059 (2)	0.0028 (15)	0.0031 (17)	0.0083 (17)
C17	0.063 (2)	0.055 (2)	0.053 (2)	−0.0015 (17)	0.0069 (18)	0.0096 (17)
C18	0.064 (2)	0.072 (2)	0.055 (2)	−0.0100 (19)	−0.0029 (19)	0.0109 (18)
C19	0.0495 (19)	0.079 (3)	0.066 (2)	0.0022 (19)	−0.002 (2)	0.018 (2)
C20	0.051 (2)	0.0555 (19)	0.057 (2)	0.0067 (16)	0.0082 (17)	0.0106 (17)
C21	0.099 (3)	0.068 (2)	0.065 (2)	0.011 (2)	0.006 (2)	−0.0031 (19)

O1—C1	1.354 (3)	C10—C12	1.527 (5)
O1—H1A	0.8200	C10—C13	1.530 (4)
O2—C20	1.357 (4)	C10—C11	1.533 (5)
O2—H2A	0.8200	C11—H11A	0.9600
N1—C8	1.271 (4)	C11—H11B	0.9600
N1—C9	1.464 (4)	C11—H11C	0.9600
N2—C14	1.276 (4)	C12—H12A	0.9600
N2—C13	1.465 (4)	C12—H12B	0.9600
C1—C2	1.377 (4)	C12—H12C	0.9600
C1—C6	1.409 (4)	C13—H13A	0.9700
C2—C3	1.371 (4)	C13—H13B	0.9700
C2—H2	0.9300	C14—C15	1.445 (4)
C3—C4	1.401 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.391 (4)
C4—C5	1.380 (4)	C15—C20	1.395 (4)
C4—C7	1.506 (4)	C16—C17	1.374 (4)
C5—C6	1.388 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.384 (5)
C6—C8	1.456 (4)	C17—C21	1.515 (4)
C7—H7A	0.9600	C18—C19	1.386 (5)
C7—H7B	0.9600	C18—H18	0.9300
C7—H7C	0.9600	C19—C20	1.377 (4)
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.524 (5)	C21—H21A	0.9600
C9—H9A	0.9700	C21—H21B	0.9600
C9—H9B	0.9700	C21—H21C	0.9600
C1—O1—H1A	109.5	C10—C11—H11B	109.5
C20—O2—H2A	109.5	H11A—C11—H11B	109.5
C8—N1—C9	119.0 (3)	C10—C11—H11C	109.5
C14—N2—C13	119.3 (3)	H11A—C11—H11C	109.5
O1—C1—C2	119.4 (3)	H11B—C11—H11C	109.5
O1—C1—C6	121.7 (3)	C10—C12—H12A	109.5
C2—C1—C6	118.9 (3)	C10—C12—H12B	109.5
C3—C2—C1	121.4 (3)	H12A—C12—H12B	109.5
C3—C2—H2	119.3	C10—C12—H12C	109.5
C1—C2—H2	119.3	H12A—C12—H12C	109.5
C2—C3—C4	121.0 (3)	H12B—C12—H12C	109.5
C2—C3—H3	119.5	N2—C13—C10	112.6 (3)
C4—C3—H3	119.5	N2—C13—H13A	109.1
C5—C4—C3	117.2 (3)	C10—C13—H13A	109.1
C5—C4—C7	122.5 (3)	N2—C13—H13B	109.1
C3—C4—C7	120.3 (3)	C10—C13—H13B	109.1
C4—C5—C6	122.8 (3)	H13A—C13—H13B	107.8
C4—C5—H5	118.6	N2—C14—C15	123.0 (3)
C6—C5—H5	118.6	N2—C14—H14	118.5
C5—C6—C1	118.6 (3)	C15—C14—H14	118.5
C5—C6—C8	120.1 (3)	C16—C15—C20	117.9 (3)
C1—C6—C8	121.3 (3)	C16—C15—C14	120.4 (3)
C4—C7—H7A	109.5	C20—C15—C14	121.7 (3)
C4—C7—H7B	109.5	C17—C16—C15	123.3 (3)
H7A—C7—H7B	109.5	C17—C16—H16	118.3
C4—C7—H7C	109.5	C15—C16—H16	118.3
H7A—C7—H7C	109.5	C16—C17—C18	117.0 (3)
H7B—C7—H7C	109.5	C16—C17—C21	121.2 (3)
N1—C8—C6	122.2 (3)	C18—C17—C21	121.9 (3)
N1—C8—H8	118.9	C17—C18—C19	121.9 (4)
C6—C8—H8	118.9	C17—C18—H18	119.0
N1—C9—C10	112.6 (3)	C19—C18—H18	119.0
N1—C9—H9A	109.1	C20—C19—C18	119.7 (3)
C10—C9—H9A	109.1	C20—C19—H19	120.2
N1—C9—H9B	109.1	C18—C19—H19	120.2
C10—C9—H9B	109.1	O2—C20—C19	119.0 (3)
H9A—C9—H9B	107.8	O2—C20—C15	120.8 (3)
C9—C10—C12	108.2 (3)	C19—C20—C15	120.2 (3)
C9—C10—C13	110.2 (3)	C17—C21—H21A	109.5
C12—C10—C13	110.4 (3)	C17—C21—H21B	109.5
C9—C10—C11	110.3 (3)	H21A—C21—H21B	109.5
C12—C10—C11	110.5 (3)	C17—C21—H21C	109.5
C13—C10—C11	107.2 (3)	H21A—C21—H21C	109.5
C10—C11—H11A	109.5	H21B—C21—H21C	109.5
O1—C1—C2—C3	179.6 (3)	C14—N2—C13—C10	−142.8 (3)
C6—C1—C2—C3	−0.3 (5)	C9—C10—C13—N2	−61.8 (4)
C1—C2—C3—C4	−0.1 (5)	C12—C10—C13—N2	57.8 (4)
C2—C3—C4—C5	−0.6 (5)	C11—C10—C13—N2	178.1 (3)
C2—C3—C4—C7	179.0 (3)	C13—N2—C14—C15	−178.5 (3)
C3—C4—C5—C6	1.7 (5)	N2—C14—C15—C16	178.3 (3)
C7—C4—C5—C6	−177.9 (3)	N2—C14—C15—C20	−1.2 (5)
C4—C5—C6—C1	−2.1 (4)	C20—C15—C16—C17	1.3 (4)
C4—C5—C6—C8	176.9 (3)	C14—C15—C16—C17	−178.3 (3)
O1—C1—C6—C5	−178.6 (3)	C15—C16—C17—C18	−1.7 (5)
C2—C1—C6—C5	1.3 (4)	C15—C16—C17—C21	177.9 (3)
O1—C1—C6—C8	2.4 (4)	C16—C17—C18—C19	1.0 (5)
C2—C1—C6—C8	−177.7 (3)	C21—C17—C18—C19	−178.7 (3)
C9—N1—C8—C6	178.2 (3)	C17—C18—C19—C20	0.2 (5)
C5—C6—C8—N1	−175.7 (3)	C18—C19—C20—O2	−179.8 (3)
C1—C6—C8—N1	3.3 (5)	C18—C19—C20—C15	−0.7 (5)
C8—N1—C9—C10	147.8 (3)	C16—C15—C20—O2	179.1 (3)
N1—C9—C10—C12	−178.1 (3)	C14—C15—C20—O2	−1.3 (5)
N1—C9—C10—C13	−57.2 (4)	C16—C15—C20—C19	0.0 (4)
N1—C9—C10—C11	60.9 (4)	C14—C15—C20—C19	179.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.89	2.620 (3)	147
O2—H2A···N2	0.82	1.88	2.609 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.89	2.620 (3)	147
O2—H2A⋯N2	0.82	1.88	2.609 (4)	147