2-Hydr-oxy-N'-(4-isopropyl-cyclo-hexyl-carbon-yl)-3-methyl-benzohydrazide.

The crystal structure of the title compound, C(18)H(26)N(2)O(3), is stabilized by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds. One of the methyl groups is disordered with occupancies of 0.51 (3):0.49 (3).

Related literature

For the properties of metallocrowns, see: Alexiou et al. (2002 ▶); Gaynor et al. (2002 ▶); Lah & Pecoraro (1989 ▶); Lehaire et al. (2002 ▶); Liu et al. (2001 ▶, 2008 ▶); Saalfrank et al. (2001 ▶).

Experimental

Crystal data

C18H26N2O3

M = 318.41

Monoclinic,

a = 16.193 (5) Å

b = 16.194 (5) Å

c = 6.856 (2) Å

β = 97.892 (4)°

V = 1780.8 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.43 × 0.26 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none T min = 0.970, T max = 0.983

8728 measured reflections

6453 independent reflections

3925 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.211

S = 1.05

6453 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900556X/jh2073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900556X/jh2073Isup2.hkl

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

C18H26N2O3	F(000) = 688
Mr = 318.41	Dx = 1.188 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5099 reflections
a = 16.193 (5) Å	θ = 2.5–26.2°
b = 16.194 (5) Å	µ = 0.08 mm−1
c = 6.856 (2) Å	T = 296 K
β = 97.892 (4)°	Block, colourless
V = 1780.8 (9) Å3	0.43 × 0.26 × 0.22 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3925 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 32.5°, θmin = 1.8°
φ and ω scans	h = −16→24
8728 measured reflections	k = −17→24
6453 independent reflections	l = −7→10

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)] = 0.080	H-atom parameters constrained
wR(F2) = 0.211	w = 1/[σ2(Fo2) + (0.0912P)2 + 2.6628P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
6453 reflections	Δρmax = 0.40 e Å−3
217 parameters	Δρmin = −0.60 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (5)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.26649 (17)	0.4109 (2)	0.1034 (4)	0.0739 (9)
H1B	0.2257	0.4290	0.1481	0.111*
O2	−0.02604 (18)	0.29519 (17)	0.2523 (4)	0.0721 (9)
O3	0.10747 (16)	0.44725 (15)	0.0967 (4)	0.0527 (7)
N1	0.01874 (18)	0.36122 (18)	−0.0854 (5)	0.0512 (9)
H1A	0.0117	0.3227	−0.1724	0.061*
N2	−0.04755 (18)	0.38761 (18)	0.0058 (5)	0.0513 (8)
H2A	−0.0782	0.4274	−0.0462	0.062*
C1	−0.458 (2)	0.3768 (18)	0.388 (6)	0.056 (4)	0.49 (3)
H1C	−0.4868	0.4194	0.3090	0.084*	0.49 (3)
H1D	−0.4921	0.3564	0.4804	0.084*	0.49 (3)
H1E	−0.4444	0.3325	0.3043	0.084*	0.49 (3)
C1'	−0.454 (2)	0.3490 (17)	0.412 (6)	0.056 (4)	0.51 (3)
H1'A	−0.5058	0.3693	0.4471	0.084*	0.51 (3)
H1'B	−0.4431	0.2950	0.4669	0.084*	0.51 (3)
H1'C	−0.4580	0.3460	0.2709	0.084*	0.51 (3)
C2	0.3959 (3)	0.3661 (4)	−0.0978 (10)	0.106 (2)
H2B	0.4317	0.3483	−0.1904	0.159*
H2C	0.4051	0.3319	0.0176	0.159*
H2D	0.4082	0.4225	−0.0618	0.159*
C3	−0.3787 (3)	0.4114 (4)	0.4969 (7)	0.0834 (15)
H3A	−0.3790	0.4699	0.4600	0.100*
C4	−0.2983 (3)	0.3734 (3)	0.2158 (6)	0.0757 (14)
H4A	−0.3073	0.4287	0.1626	0.091*
H4B	−0.3448	0.3394	0.1591	0.091*
C5	−0.3791 (4)	0.4114 (5)	0.7111 (8)	0.119 (2)
H5A	−0.4301	0.4355	0.7407	0.179*
H5B	−0.3326	0.4430	0.7733	0.179*
H5C	−0.3748	0.3556	0.7591	0.179*
C6	−0.2185 (2)	0.3391 (3)	0.1563 (6)	0.0697 (12)
H6A	−0.2224	0.3394	0.0138	0.084*
H6B	−0.2116	0.2824	0.2005	0.084*
C7	0.2006 (3)	0.3240 (3)	−0.4629 (6)	0.0659 (12)
H7A	0.1872	0.3061	−0.5923	0.079*
C8	0.2827 (3)	0.3312 (3)	−0.3797 (7)	0.0722 (13)
H8A	0.3242	0.3168	−0.4546	0.087*
C9	−0.2194 (3)	0.4244 (3)	0.5271 (6)	0.0668 (12)
H9A	−0.2261	0.4820	0.4885	0.080*
H9B	−0.2155	0.4219	0.6694	0.080*
C10	0.3056 (3)	0.3589 (3)	−0.1909 (7)	0.0667 (12)
C11	−0.1385 (2)	0.3919 (3)	0.4654 (6)	0.0639 (11)
H11A	−0.0927	0.4272	0.5202	0.077*
H11B	−0.1278	0.3368	0.5182	0.077*
C12	−0.2964 (2)	0.3765 (3)	0.4368 (6)	0.0594 (11)
H12A	−0.2903	0.3197	0.4858	0.071*
C13	0.1385 (3)	0.3435 (2)	−0.3521 (5)	0.0519 (10)
H13A	0.0829	0.3375	−0.4057	0.062*
C14	−0.0656 (2)	0.3531 (2)	0.1735 (5)	0.0489 (9)
C15	0.2426 (2)	0.3815 (2)	−0.0817 (6)	0.0525 (10)
C16	−0.1424 (2)	0.3893 (2)	0.2434 (5)	0.0491 (9)
H16A	−0.1494	0.4459	0.1934	0.059*
C17	0.1590 (2)	0.3722 (2)	−0.1597 (5)	0.0438 (9)
C18	0.0941 (2)	0.3959 (2)	−0.0379 (5)	0.0432 (9)

	U11	U22	U33	U12	U13	U23
O1	0.0567 (17)	0.097 (2)	0.0653 (19)	−0.0119 (16)	0.0002 (14)	−0.0117 (16)
O2	0.078 (2)	0.0557 (17)	0.084 (2)	0.0235 (15)	0.0142 (16)	0.0192 (15)
O3	0.0640 (16)	0.0435 (14)	0.0507 (15)	−0.0001 (12)	0.0089 (12)	−0.0073 (12)
N1	0.0474 (18)	0.0430 (17)	0.065 (2)	−0.0004 (14)	0.0150 (15)	−0.0112 (14)
N2	0.0483 (18)	0.0446 (17)	0.063 (2)	0.0103 (14)	0.0156 (15)	0.0052 (15)
C1	0.052 (4)	0.062 (15)	0.054 (8)	0.001 (11)	0.007 (5)	−0.002 (10)
C1'	0.052 (4)	0.062 (15)	0.054 (8)	0.001 (11)	0.007 (5)	−0.002 (10)
C2	0.049 (3)	0.133 (5)	0.137 (5)	−0.003 (3)	0.021 (3)	0.000 (4)
C3	0.066 (3)	0.111 (4)	0.078 (3)	0.003 (3)	0.026 (2)	−0.003 (3)
C4	0.052 (2)	0.114 (4)	0.060 (3)	0.003 (2)	0.005 (2)	−0.012 (2)
C5	0.089 (4)	0.182 (7)	0.091 (4)	−0.019 (4)	0.029 (3)	−0.020 (4)
C6	0.055 (2)	0.094 (3)	0.060 (2)	−0.002 (2)	0.0059 (19)	−0.022 (2)
C7	0.091 (3)	0.052 (2)	0.060 (2)	−0.007 (2)	0.028 (2)	−0.0087 (19)
C8	0.077 (3)	0.061 (3)	0.087 (3)	0.001 (2)	0.041 (3)	−0.007 (2)
C9	0.066 (3)	0.080 (3)	0.056 (2)	−0.004 (2)	0.013 (2)	−0.015 (2)
C10	0.052 (2)	0.064 (3)	0.087 (3)	−0.0014 (19)	0.021 (2)	0.004 (2)
C11	0.055 (2)	0.079 (3)	0.057 (2)	−0.007 (2)	0.0021 (19)	−0.006 (2)
C12	0.059 (2)	0.062 (2)	0.058 (2)	−0.0005 (19)	0.0116 (19)	0.0021 (19)
C13	0.062 (2)	0.042 (2)	0.052 (2)	−0.0038 (17)	0.0107 (18)	−0.0033 (16)
C14	0.050 (2)	0.039 (2)	0.058 (2)	0.0026 (17)	0.0056 (17)	0.0026 (17)
C15	0.051 (2)	0.049 (2)	0.058 (2)	−0.0037 (17)	0.0101 (18)	0.0030 (17)
C16	0.052 (2)	0.043 (2)	0.053 (2)	0.0033 (16)	0.0103 (17)	0.0060 (16)
C17	0.049 (2)	0.0339 (18)	0.050 (2)	−0.0022 (15)	0.0113 (16)	0.0022 (15)
C18	0.052 (2)	0.0313 (17)	0.046 (2)	0.0023 (15)	0.0077 (16)	0.0037 (16)

O1—C15	1.360 (5)	C4—H4B	0.9700
O1—H1B	0.8200	C5—H5A	0.9600
O2—C14	1.220 (4)	C5—H5B	0.9600
O3—C18	1.239 (4)	C5—H5C	0.9600
N1—C18	1.342 (5)	C6—C16	1.527 (6)
N1—N2	1.382 (4)	C6—H6A	0.9700
N1—H1A	0.8600	C6—H6B	0.9700
N2—C14	1.346 (5)	C7—C13	1.376 (6)
N2—H2A	0.8600	C7—C8	1.378 (7)
C1—C3	1.50 (4)	C7—H7A	0.9300
C1—H1C	0.9600	C8—C10	1.372 (6)
C1—H1D	0.9600	C8—H8A	0.9300
C1—H1E	0.9600	C9—C11	1.525 (6)
C1'—C3	1.63 (4)	C9—C12	1.526 (6)
C1'—H1'A	0.9600	C9—H9A	0.9700
C1'—H1'B	0.9600	C9—H9B	0.9700
C1'—H1'C	0.9600	C10—C15	1.394 (6)
C2—C10	1.518 (7)	C11—C16	1.515 (5)
C2—H2B	0.9600	C11—H11A	0.9700
C2—H2C	0.9600	C11—H11B	0.9700
C2—H2D	0.9600	C12—H12A	0.9800
C3—C5	1.469 (7)	C13—C17	1.395 (5)
C3—C12	1.554 (6)	C13—H13A	0.9300
C3—H3A	0.9800	C14—C16	1.511 (5)
C4—C12	1.512 (6)	C15—C17	1.395 (5)
C4—C6	1.514 (6)	C16—H16A	0.9800
C4—H4A	0.9700	C17—C18	1.479 (5)
C15—O1—H1B	109.5	H6A—C6—H6B	107.9
C18—N1—N2	119.8 (3)	C13—C7—C8	119.2 (4)
C18—N1—H1A	120.1	C13—C7—H7A	120.4
N2—N1—H1A	120.1	C8—C7—H7A	120.4
C14—N2—N1	122.1 (3)	C10—C8—C7	122.6 (4)
C14—N2—H2A	118.9	C10—C8—H8A	118.7
N1—N2—H2A	118.9	C7—C8—H8A	118.7
C3—C1—H1C	109.5	C11—C9—C12	113.4 (3)
C3—C1—H1D	109.5	C11—C9—H9A	108.9
C3—C1—H1E	109.5	C12—C9—H9A	108.9
C3—C1'—H1'A	109.5	C11—C9—H9B	108.9
C3—C1'—H1'B	109.5	C12—C9—H9B	108.9
H1'A—C1'—H1'B	109.5	H9A—C9—H9B	107.7
C3—C1'—H1'C	109.5	C8—C10—C15	118.0 (4)
H1'A—C1'—H1'C	109.5	C8—C10—C2	122.8 (4)
H1'B—C1'—H1'C	109.5	C15—C10—C2	119.2 (4)
C10—C2—H2B	109.5	C16—C11—C9	111.7 (3)
C10—C2—H2C	109.5	C16—C11—H11A	109.3
H2B—C2—H2C	109.5	C9—C11—H11A	109.3
C10—C2—H2D	109.5	C16—C11—H11B	109.3
H2B—C2—H2D	109.5	C9—C11—H11B	109.3
H2C—C2—H2D	109.5	H11A—C11—H11B	107.9
C5—C3—C1	112.2 (16)	C4—C12—C9	109.0 (4)
C5—C3—C12	112.8 (4)	C4—C12—C3	112.2 (4)
C1—C3—C12	115.8 (16)	C9—C12—C3	112.9 (4)
C5—C3—C1'	104.6 (14)	C4—C12—H12A	107.5
C1—C3—C1'	17.0 (13)	C9—C12—H12A	107.5
C12—C3—C1'	107.9 (14)	C3—C12—H12A	107.5
C5—C3—H3A	104.9	C7—C13—C17	120.1 (4)
C1—C3—H3A	104.9	C7—C13—H13A	119.9
C12—C3—H3A	104.9	C17—C13—H13A	119.9
C1'—C3—H3A	121.9	O2—C14—N2	122.3 (3)
C12—C4—C6	112.4 (4)	O2—C14—C16	124.3 (3)
C12—C4—H4A	109.1	N2—C14—C16	113.3 (3)
C6—C4—H4A	109.1	O1—C15—C10	117.2 (4)
C12—C4—H4B	109.1	O1—C15—C17	122.1 (3)
C6—C4—H4B	109.1	C10—C15—C17	120.6 (4)
H4A—C4—H4B	107.8	C14—C16—C11	114.0 (3)
C3—C5—H5A	109.5	C14—C16—C6	108.9 (3)
C3—C5—H5B	109.5	C11—C16—C6	109.1 (3)
H5A—C5—H5B	109.5	C14—C16—H16A	108.2
C3—C5—H5C	109.5	C11—C16—H16A	108.2
H5A—C5—H5C	109.5	C6—C16—H16A	108.2
H5B—C5—H5C	109.5	C15—C17—C13	119.4 (3)
C4—C6—C16	111.9 (4)	C15—C17—C18	118.9 (3)
C4—C6—H6A	109.2	C13—C17—C18	121.7 (3)
C16—C6—H6A	109.2	O3—C18—N1	121.5 (3)
C4—C6—H6B	109.2	O3—C18—C17	122.0 (3)
C16—C6—H6B	109.2	N1—C18—C17	116.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.05	2.821 (4)	149
O1—H1B···O3	0.82	1.92	2.636 (4)	145
N2—H2A···O3ii	0.86	2.10	2.898 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.05	2.821 (4)	149
O1—H1B⋯O3	0.82	1.92	2.636 (4)	145
N2—H2A⋯O3ii	0.86	2.10	2.898 (4)	154

Symmetry codes: (i) ; (ii) .