tert-Butyl N-(4-hy-droxy-benz-yl)-N-[4-(prop-2-yn-yloxy)benz-yl]carbamate.

In the crystal structure of the title compound, C(22)H(25)NO(4), inter-molecular O-H⋯O hydrogen bonds involving the hy-droxy group of the 4-(amimometh-yl)phenol fragment and the C=O group connect the mol-ecules into infinite chains along the c axis. Two C atoms of the propyne group are disordered over two sites with occupancy factors of 0.53 (2) and 0.47 (2).

Related literature

For applications of the title compound, see: Späth & König (2010 ▶); Juríček et al. (2011 ▶). For the synthesis of the title compound, see: Kim et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H25NO4

M = 367.43

Monoclinic,

a = 18.6904 (8) Å

b = 6.2611 (4) Å

c = 17.3567 (7) Å

β = 96.791 (1)°

V = 2016.87 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.41 × 0.37 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.957, T max = 0.976

15741 measured reflections

3750 independent reflections

2099 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.149

S = 1.00

3750 reflections

268 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.19 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681103683X/kj2185sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103683X/kj2185Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103683X/kj2185Isup3.cml

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

C22H25NO4	F(000) = 784
Mr = 367.43	Dx = 1.210 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9726 reflections
a = 18.6904 (8) Å	θ = 3.0–27.4°
b = 6.2611 (4) Å	µ = 0.08 mm−1
c = 17.3567 (7) Å	T = 296 K
β = 96.791 (1)°	Chunk, colorless
V = 2016.87 (18) Å3	0.41 × 0.37 × 0.29 mm
Z = 4

Rigaku R-AXIS RAPID/ZJUG diffractometer	3750 independent reflections
Radiation source: rolling anode	2099 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 10.00 pixels mm-1	θmax = 25.5°, θmin = 3.0°
ω scans	h = −22→22
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −7→7
Tmin = 0.957, Tmax = 0.976	l = −21→19
15741 measured reflections

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0635P)2 + 0.6687P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3750 reflections	Δρmax = 0.26 e Å−3
268 parameters	Δρmin = −0.19 e Å−3
4 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: 0.0155 (18)

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	0.17241 (12)	0.2936 (3)	0.76205 (9)	0.0818 (6)
H1	0.1833	0.3985	0.7892	0.123*
O2	0.43006 (9)	0.6806 (3)	0.13104 (10)	0.0726 (5)
O3	0.13748 (8)	0.5836 (3)	0.40395 (8)	0.0592 (5)
O4	0.19445 (10)	0.8841 (3)	0.36950 (9)	0.0695 (5)
N1	0.25604 (11)	0.6051 (3)	0.42845 (10)	0.0605 (5)
C1	0.19319 (13)	0.3250 (4)	0.68966 (12)	0.0564 (6)
C2	0.22502 (14)	0.5106 (4)	0.66891 (13)	0.0643 (7)
H2	0.2334	0.6214	0.7046	0.077*
C3	0.24466 (15)	0.5329 (4)	0.59494 (13)	0.0664 (7)
H3	0.2663	0.6593	0.5816	0.080*
C4	0.23302 (11)	0.3722 (4)	0.54024 (12)	0.0513 (6)
C5	0.20066 (14)	0.1883 (4)	0.56236 (13)	0.0648 (7)
H5	0.1919	0.0776	0.5268	0.078*
C6	0.18094 (15)	0.1640 (4)	0.63598 (14)	0.0712 (7)
H6	0.1592	0.0378	0.6493	0.085*
C7	0.25534 (14)	0.3881 (4)	0.45966 (13)	0.0633 (7)
H7A	0.3032	0.3276	0.4604	0.076*
H7B	0.2227	0.3019	0.4248	0.076*
C8	0.32381 (13)	0.7155 (5)	0.42417 (13)	0.0712 (8)
H8A	0.3601	0.6535	0.4622	0.085*
H8B	0.3180	0.8639	0.4382	0.085*
C9	0.35077 (12)	0.7072 (4)	0.34535 (12)	0.0584 (6)
C10	0.39496 (15)	0.8655 (5)	0.32395 (15)	0.0776 (8)
H10	0.4067	0.9780	0.3581	0.093*
C11	0.42283 (15)	0.8647 (5)	0.25335 (15)	0.0762 (8)
H11	0.4527	0.9746	0.2404	0.091*
C12	0.40561 (12)	0.6991 (4)	0.20300 (13)	0.0579 (6)
C13	0.36058 (13)	0.5388 (4)	0.22214 (14)	0.0649 (7)
H13	0.3485	0.4271	0.1877	0.078*
C14	0.33342 (13)	0.5442 (4)	0.29254 (14)	0.0652 (7)
H14	0.3027	0.4359	0.3049	0.078*
C15	0.48249 (14)	0.8306 (4)	0.11323 (15)	0.0756 (8)
H15A	0.5194	0.8459	0.1571	0.091*
H15	0.4601	0.9688	0.1024	0.091*	0.532 (4)
H15B	0.5046	0.7474	0.0752	0.091*	0.468 (4)
C16A	0.5155 (2)	0.7544 (7)	0.0443 (2)	0.0661 (14)	0.532 (4)
C17A	0.5407 (3)	0.6902 (8)	−0.0069 (2)	0.0760 (17)	0.532 (4)
H17A	0.5615	0.6372	−0.0491	0.091*	0.532 (4)
C16B	0.4509 (3)	1.0432 (7)	0.0868 (3)	0.0689 (17)	0.468 (4)
C17B	0.4307 (4)	1.2108 (7)	0.0727 (4)	0.086 (2)	0.468 (4)
H17B	0.4141	1.3484	0.0611	0.103*	0.468 (4)
C18	0.19532 (13)	0.7046 (4)	0.39779 (12)	0.0566 (6)
C19	0.06391 (13)	0.6547 (4)	0.37645 (14)	0.0623 (6)
C20	0.05670 (17)	0.6953 (5)	0.28996 (16)	0.0932 (10)
H20A	0.0806	0.8265	0.2800	0.140*
H20B	0.0066	0.7054	0.2703	0.140*
H20C	0.0783	0.5797	0.2647	0.140*
C21	0.01977 (15)	0.4612 (5)	0.39359 (16)	0.0809 (8)
H21A	0.0320	0.3431	0.3624	0.121*
H21B	−0.0306	0.4932	0.3818	0.121*
H21C	0.0299	0.4245	0.4475	0.121*
C22	0.04566 (18)	0.8454 (5)	0.4239 (2)	0.1049 (11)
H22A	0.0587	0.8160	0.4780	0.157*
H22B	−0.0051	0.8734	0.4144	0.157*
H22C	0.0718	0.9680	0.4093	0.157*

	U11	U22	U33	U12	U13	U23
O1	0.1286 (16)	0.0695 (13)	0.0529 (10)	−0.0072 (12)	0.0346 (10)	0.0001 (9)
O2	0.0827 (12)	0.0748 (13)	0.0651 (11)	−0.0114 (10)	0.0292 (9)	−0.0031 (9)
O3	0.0653 (10)	0.0561 (10)	0.0566 (9)	0.0006 (8)	0.0088 (7)	0.0070 (8)
O4	0.0927 (13)	0.0557 (11)	0.0608 (10)	−0.0063 (9)	0.0113 (9)	0.0095 (8)
N1	0.0651 (12)	0.0708 (14)	0.0463 (10)	0.0014 (11)	0.0101 (9)	0.0085 (10)
C1	0.0717 (15)	0.0532 (15)	0.0454 (12)	0.0012 (12)	0.0109 (11)	0.0046 (11)
C2	0.0915 (18)	0.0562 (16)	0.0455 (13)	−0.0079 (14)	0.0090 (12)	−0.0060 (11)
C3	0.0921 (18)	0.0566 (16)	0.0522 (14)	−0.0155 (13)	0.0155 (13)	−0.0014 (12)
C4	0.0559 (13)	0.0566 (15)	0.0412 (11)	0.0052 (11)	0.0046 (9)	0.0014 (10)
C5	0.0825 (17)	0.0591 (16)	0.0529 (14)	−0.0081 (13)	0.0089 (12)	−0.0107 (12)
C6	0.102 (2)	0.0533 (16)	0.0612 (15)	−0.0136 (14)	0.0206 (14)	−0.0054 (12)
C7	0.0765 (16)	0.0657 (17)	0.0485 (13)	0.0155 (13)	0.0105 (11)	0.0065 (11)
C8	0.0694 (16)	0.093 (2)	0.0519 (13)	−0.0119 (15)	0.0077 (12)	−0.0025 (13)
C9	0.0558 (13)	0.0720 (17)	0.0475 (12)	−0.0059 (12)	0.0061 (10)	0.0016 (12)
C10	0.0908 (19)	0.087 (2)	0.0562 (15)	−0.0329 (17)	0.0127 (14)	−0.0139 (14)
C11	0.0831 (18)	0.084 (2)	0.0631 (16)	−0.0333 (16)	0.0160 (13)	−0.0054 (14)
C12	0.0586 (13)	0.0661 (16)	0.0506 (13)	0.0006 (12)	0.0131 (11)	0.0036 (12)
C13	0.0726 (16)	0.0621 (16)	0.0632 (15)	−0.0091 (13)	0.0215 (12)	−0.0066 (12)
C14	0.0676 (15)	0.0668 (17)	0.0636 (15)	−0.0105 (13)	0.0179 (12)	0.0011 (13)
C15	0.0773 (18)	0.078 (2)	0.0759 (17)	−0.0071 (15)	0.0281 (14)	0.0091 (15)
C16A	0.074 (3)	0.065 (3)	0.059 (3)	−0.008 (3)	0.006 (2)	0.015 (2)
C17A	0.099 (4)	0.082 (4)	0.052 (3)	0.004 (3)	0.032 (3)	0.003 (3)
C16B	0.078 (4)	0.074 (4)	0.058 (3)	−0.014 (3)	0.022 (3)	−0.009 (3)
C17B	0.124 (6)	0.056 (4)	0.083 (4)	−0.005 (4)	0.030 (4)	−0.002 (3)
C18	0.0739 (16)	0.0567 (16)	0.0407 (12)	−0.0044 (13)	0.0126 (11)	−0.0007 (11)
C19	0.0630 (14)	0.0604 (16)	0.0641 (14)	0.0043 (12)	0.0096 (12)	−0.0031 (12)
C20	0.100 (2)	0.100 (2)	0.0728 (17)	−0.0091 (19)	−0.0149 (16)	0.0252 (17)
C21	0.0818 (18)	0.080 (2)	0.0820 (19)	−0.0154 (16)	0.0134 (15)	0.0000 (15)
C22	0.091 (2)	0.078 (2)	0.150 (3)	0.0079 (17)	0.034 (2)	−0.037 (2)

O1—C1	1.372 (3)	C10—H10	0.9300
O1—H1	0.8200	C11—C12	1.369 (3)
O2—C12	1.385 (3)	C11—H11	0.9300
O2—C15	1.417 (3)	C12—C13	1.376 (3)
O3—C18	1.335 (3)	C13—C14	1.378 (3)
O3—C19	1.470 (3)	C13—H13	0.9300
O4—C18	1.226 (3)	C14—H14	0.9300
N1—C18	1.348 (3)	C15—C16A	1.488 (3)
N1—C8	1.452 (3)	C15—C16B	1.506 (3)
N1—C7	1.464 (3)	C15—H15A	0.9700
C1—C2	1.373 (3)	C15—H15	0.9700
C1—C6	1.374 (3)	C15—H15B	0.9700
C2—C3	1.383 (3)	C16A—C17A	1.128 (3)
C2—H2	0.9300	C16A—H15B	0.5978
C3—C4	1.383 (3)	C17A—H17A	0.9300
C3—H3	0.9300	C16B—C17B	1.132 (3)
C4—C5	1.376 (3)	C17B—H17B	0.9300
C4—C7	1.509 (3)	C19—C22	1.512 (4)
C5—C6	1.379 (3)	C19—C20	1.513 (4)
C5—H5	0.9300	C19—C21	1.515 (4)
C6—H6	0.9300	C20—H20A	0.9600
C7—H7A	0.9700	C20—H20B	0.9600
C7—H7B	0.9700	C20—H20C	0.9600
C8—C9	1.514 (3)	C21—H21A	0.9600
C8—H8A	0.9700	C21—H21B	0.9600
C8—H8B	0.9700	C21—H21C	0.9600
C9—C10	1.369 (3)	C22—H22A	0.9600
C9—C14	1.384 (3)	C22—H22B	0.9600
C10—C11	1.387 (3)	C22—H22C	0.9600
C1—O1—H1	109.5	C14—C13—H13	120.1
C12—O2—C15	116.86 (19)	C13—C14—C9	121.6 (2)
C18—O3—C19	122.50 (19)	C13—C14—H14	119.2
C18—N1—C8	117.3 (2)	C9—C14—H14	119.2
C18—N1—C7	122.1 (2)	O2—C15—C16A	109.0 (3)
C8—N1—C7	120.4 (2)	O2—C15—C16B	113.3 (3)
C2—C1—O1	122.7 (2)	C16A—C15—C16B	102.9 (3)
C2—C1—C6	119.1 (2)	O2—C15—H15A	109.9
O1—C1—C6	118.3 (2)	C16A—C15—H15A	109.9
C1—C2—C3	120.0 (2)	C16B—C15—H15A	111.6
C1—C2—H2	120.0	O2—C15—H15	109.9
C3—C2—H2	120.0	C16A—C15—H15	109.9
C4—C3—C2	121.8 (2)	H15A—C15—H15	108.3
C4—C3—H3	119.1	O2—C15—H15B	98.9
C2—C3—H3	119.1	C16B—C15—H15B	116.8
C5—C4—C3	117.1 (2)	H15A—C15—H15B	105.5
C5—C4—C7	119.5 (2)	H15—C15—H15B	123.8
C3—C4—C7	123.4 (2)	C17A—C16A—C15	177.7 (5)
C4—C5—C6	121.7 (2)	C17A—C16A—H15B	154.1
C4—C5—H5	119.2	C16A—C17A—H17A	180.0
C6—C5—H5	119.2	C17B—C16B—C15	173.8 (6)
C1—C6—C5	120.4 (2)	C16B—C17B—H17B	180.0
C1—C6—H6	119.8	O4—C18—O3	125.5 (2)
C5—C6—H6	119.8	O4—C18—N1	123.5 (2)
N1—C7—C4	114.8 (2)	O3—C18—N1	111.0 (2)
N1—C7—H7A	108.6	O3—C19—C22	109.0 (2)
C4—C7—H7A	108.6	O3—C19—C20	110.1 (2)
N1—C7—H7B	108.6	C22—C19—C20	114.1 (3)
C4—C7—H7B	108.6	O3—C19—C21	101.8 (2)
H7A—C7—H7B	107.5	C22—C19—C21	111.2 (2)
N1—C8—C9	114.55 (19)	C20—C19—C21	110.0 (2)
N1—C8—H8A	108.6	C19—C20—H20A	109.5
C9—C8—H8A	108.6	C19—C20—H20B	109.5
N1—C8—H8B	108.6	H20A—C20—H20B	109.5
C9—C8—H8B	108.6	C19—C20—H20C	109.5
H8A—C8—H8B	107.6	H20A—C20—H20C	109.5
C10—C9—C14	117.1 (2)	H20B—C20—H20C	109.5
C10—C9—C8	119.8 (2)	C19—C21—H21A	109.5
C14—C9—C8	123.1 (2)	C19—C21—H21B	109.5
C9—C10—C11	122.6 (2)	H21A—C21—H21B	109.5
C9—C10—H10	118.7	C19—C21—H21C	109.5
C11—C10—H10	118.7	H21A—C21—H21C	109.5
C12—C11—C10	118.8 (2)	H21B—C21—H21C	109.5
C12—C11—H11	120.6	C19—C22—H22A	109.5
C10—C11—H11	120.6	C19—C22—H22B	109.5
C11—C12—C13	120.2 (2)	H22A—C22—H22B	109.5
C11—C12—O2	124.1 (2)	C19—C22—H22C	109.5
C13—C12—O2	115.7 (2)	H22A—C22—H22C	109.5
C12—C13—C14	119.7 (2)	H22B—C22—H22C	109.5
C12—C13—H13	120.1
O1—C1—C2—C3	−179.9 (2)	C10—C11—C12—C13	0.9 (4)
C6—C1—C2—C3	−0.4 (4)	C10—C11—C12—O2	−180.0 (2)
C1—C2—C3—C4	0.1 (4)	C15—O2—C12—C11	7.5 (4)
C2—C3—C4—C5	0.2 (4)	C15—O2—C12—C13	−173.4 (2)
C2—C3—C4—C7	−178.4 (2)	C11—C12—C13—C14	−0.6 (4)
C3—C4—C5—C6	−0.4 (4)	O2—C12—C13—C14	−179.8 (2)
C7—C4—C5—C6	178.3 (2)	C12—C13—C14—C9	−0.5 (4)
C2—C1—C6—C5	0.3 (4)	C10—C9—C14—C13	1.3 (4)
O1—C1—C6—C5	179.8 (2)	C8—C9—C14—C13	−178.2 (2)
C4—C5—C6—C1	0.1 (4)	C12—O2—C15—C16A	165.7 (3)
C18—N1—C7—C4	−79.6 (3)	C12—O2—C15—C16B	−80.4 (3)
C8—N1—C7—C4	105.1 (2)	C19—O3—C18—O4	0.1 (3)
C5—C4—C7—N1	151.9 (2)	C19—O3—C18—N1	178.88 (18)
C3—C4—C7—N1	−29.5 (3)	C8—N1—C18—O4	−2.7 (3)
C18—N1—C8—C9	−77.4 (3)	C7—N1—C18—O4	−178.1 (2)
C7—N1—C8—C9	98.1 (3)	C8—N1—C18—O3	178.44 (18)
N1—C8—C9—C10	154.0 (3)	C7—N1—C18—O3	3.0 (3)
N1—C8—C9—C14	−26.5 (4)	C18—O3—C19—C22	−64.6 (3)
C14—C9—C10—C11	−1.1 (4)	C18—O3—C19—C20	61.2 (3)
C8—C9—C10—C11	178.5 (3)	C18—O3—C19—C21	177.9 (2)
C9—C10—C11—C12	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	1.94	2.745 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.82	1.94	2.745 (2)	167

Symmetry code: (i) .