tert-Butyl N-{2-[bis-(prop-2-yn-1-yl)amino]-phen-yl}carbamate.

In the crystal of the title compound, C(17)H(20)N(2)O(2), the molecules are linked by C-H⋯O interactions. Intra-molecular C-H⋯O and N-H⋯N hydrogen bonds also occur.

Related literature

For applications of alkyne scaffolds in biology, medicinal and materials chemistry, see: Diederich et al. (2005 ▶); Stang & Diederich (1995 ▶); Lam et al. (1988 ▶); Patai (1994 ▶). For background to click chemistry, which involves 1,3-dipolar cyclo­addition of an alkyne with an azide and is an efficient and highly versatile tool that has allowed the preparation of a variety of macromolecule conjugates such as sugars, peptides or proteins and DNA, see: Rostovtsev et al. (2002 ▶). For the synthesis, see: Lilienkampf et al. (2009 ▶). For inter­molecular inter­actions, see: Steiner & Desiraju (1998 ▶). For intra­molecular C—H⋯O hydrogen bonds, see: Smith et al. (1993 ▶).

Experimental

Crystal data

C17H20N2O2

M = 284.35

Monoclinic,

a = 19.1936 (12) Å

b = 8.7181 (4) Å

c = 19.7619 (9) Å

β = 99.513 (5)°

V = 3261.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.40 × 0.39 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.953, T max = 1.000

6969 measured reflections

4389 independent reflections

2427 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.156

S = 0.96

4389 reflections

194 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016862/zj2008sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016862/zj2008Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016862/zj2008Isup3.cml

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

C17H20N2O2	F(000) = 1216.0
Mr = 284.35	Dx = 1.158 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4389 reflections
a = 19.1936 (12) Å	θ = 3.2–29.0°
b = 8.7181 (4) Å	µ = 0.08 mm−1
c = 19.7619 (9) Å	T = 293 K
β = 99.513 (5)°	Block, colourless
V = 3261.3 (3) Å3	0.40 × 0.39 × 0.38 mm
Z = 8

Oxford Diffraction Xcalibur Eos diffractometer	4389 independent reflections
Radiation source: fine-focus sealed tube	2427 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 29.1°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −24→7
Tmin = 0.953, Tmax = 1.000	k = −10→10
6969 measured reflections	l = −23→26

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0754P)2 + 1.325P] where P = (Fo2 + 2Fc2)/3
4389 reflections	(Δ/σ)max = 0.05
194 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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
HN1	0.1292 (11)	0.706 (2)	0.4601 (9)	0.038 (5)*
N1	0.13858 (9)	0.78587 (19)	0.47962 (8)	0.0397 (4)
O2	0.05794 (7)	0.71231 (15)	0.53892 (6)	0.0505 (4)
N2	0.17096 (8)	0.68525 (17)	0.35922 (7)	0.0399 (4)
C1	0.18983 (9)	0.8707 (2)	0.45262 (8)	0.0362 (4)
O1	0.11848 (8)	0.93110 (16)	0.57014 (6)	0.0548 (4)
C13	0.10630 (10)	0.8202 (2)	0.53354 (8)	0.0380 (4)
C6	0.20658 (10)	0.8197 (2)	0.38966 (8)	0.0383 (4)
C2	0.22421 (11)	0.9975 (2)	0.48421 (10)	0.0454 (5)
H2	0.2130	1.0324	0.5256	0.055*
C11	0.19018 (12)	0.4288 (3)	0.31791 (9)	0.0510 (5)
C5	0.25792 (11)	0.8980 (2)	0.36113 (10)	0.0507 (5)
H5	0.2691	0.8655	0.3194	0.061*
C10	0.21577 (11)	0.5866 (2)	0.32379 (9)	0.0476 (5)
H10A	0.2168	0.6274	0.2783	0.057*
H10B	0.2637	0.5879	0.3489	0.057*
C8	0.10589 (12)	0.7963 (3)	0.25187 (10)	0.0586 (6)
C3	0.27519 (12)	1.0729 (2)	0.45480 (11)	0.0544 (5)
H3	0.2980	1.1581	0.4765	0.065*
C7	0.10173 (11)	0.7167 (2)	0.31671 (9)	0.0491 (5)
H7A	0.0771	0.6202	0.3064	0.059*
H7B	0.0739	0.7786	0.3431	0.059*
C14	0.00843 (11)	0.7249 (2)	0.58831 (9)	0.0484 (5)
C4	0.29225 (12)	1.0225 (2)	0.39370 (12)	0.0576 (6)
H4	0.3270	1.0727	0.3744	0.069*
C12	0.17318 (14)	0.2999 (3)	0.31334 (12)	0.0681 (7)
H12	0.1597	0.1974	0.3097	0.082*
C15	−0.03735 (16)	0.5849 (3)	0.57144 (14)	0.0852 (9)
H15A	−0.0629	0.5935	0.5255	0.128*
H15B	−0.0701	0.5772	0.6031	0.128*
H15C	−0.0081	0.4949	0.5750	0.128*
C9	0.11141 (16)	0.8551 (4)	0.20009 (13)	0.0838 (8)
H9	0.1158	0.9020	0.1587	0.101*
C16	0.04878 (15)	0.7145 (4)	0.66033 (11)	0.0833 (9)
H16A	0.0750	0.6203	0.6656	0.125*
H16B	0.0163	0.7169	0.6924	0.125*
H16C	0.0808	0.7996	0.6689	0.125*
C17	−0.03353 (15)	0.8709 (3)	0.57635 (15)	0.0854 (9)
H17A	−0.0585	0.8727	0.5300	0.128*
H17B	−0.0021	0.9572	0.5837	0.128*
H17C	−0.0668	0.8759	0.6076	0.128*

	U11	U22	U33	U12	U13	U23
N1	0.0456 (10)	0.0393 (9)	0.0381 (8)	−0.0030 (7)	0.0187 (7)	−0.0042 (7)
O2	0.0517 (9)	0.0599 (8)	0.0465 (7)	−0.0109 (7)	0.0271 (6)	−0.0086 (6)
N2	0.0396 (9)	0.0496 (9)	0.0328 (7)	0.0035 (7)	0.0129 (6)	0.0014 (6)
C1	0.0340 (10)	0.0386 (9)	0.0379 (9)	0.0065 (8)	0.0118 (7)	0.0075 (7)
O1	0.0565 (9)	0.0634 (9)	0.0486 (7)	−0.0082 (7)	0.0212 (6)	−0.0186 (7)
C13	0.0358 (10)	0.0462 (10)	0.0332 (8)	0.0030 (8)	0.0094 (7)	0.0006 (7)
C6	0.0362 (10)	0.0424 (10)	0.0386 (9)	0.0062 (8)	0.0126 (7)	0.0083 (7)
C2	0.0431 (11)	0.0422 (10)	0.0530 (11)	0.0036 (9)	0.0133 (8)	−0.0008 (8)
C11	0.0530 (13)	0.0616 (14)	0.0412 (10)	0.0101 (11)	0.0160 (9)	−0.0043 (9)
C5	0.0506 (13)	0.0553 (12)	0.0518 (11)	0.0017 (10)	0.0250 (9)	0.0092 (9)
C10	0.0457 (12)	0.0610 (13)	0.0391 (9)	0.0088 (10)	0.0155 (8)	−0.0007 (8)
C8	0.0522 (14)	0.0731 (15)	0.0499 (12)	0.0075 (12)	0.0066 (9)	0.0173 (10)
C3	0.0455 (13)	0.0434 (11)	0.0756 (14)	−0.0007 (10)	0.0141 (10)	0.0011 (10)
C7	0.0418 (12)	0.0638 (13)	0.0432 (10)	0.0022 (10)	0.0113 (8)	0.0076 (9)
C14	0.0456 (12)	0.0621 (12)	0.0435 (10)	0.0018 (10)	0.0247 (8)	0.0024 (9)
C4	0.0466 (13)	0.0529 (12)	0.0794 (14)	−0.0020 (10)	0.0287 (11)	0.0122 (11)
C12	0.0762 (18)	0.0616 (15)	0.0727 (15)	0.0037 (13)	0.0307 (13)	−0.0087 (11)
C15	0.081 (2)	0.095 (2)	0.0936 (18)	−0.0271 (16)	0.0533 (15)	−0.0110 (15)
C9	0.081 (2)	0.108 (2)	0.0634 (15)	0.0147 (17)	0.0150 (13)	0.0378 (15)
C16	0.086 (2)	0.121 (2)	0.0472 (13)	0.0107 (18)	0.0253 (12)	0.0175 (13)
C17	0.0630 (17)	0.093 (2)	0.110 (2)	0.0268 (15)	0.0427 (15)	0.0300 (16)

N1—C13	1.352 (2)	C8—C7	1.471 (3)
N1—C1	1.404 (2)	C3—C4	1.374 (3)
N1—HN1	0.801 (19)	C3—H3	0.9300
O2—C13	1.338 (2)	C7—H7A	0.9700
O2—C14	1.475 (2)	C7—H7B	0.9700
N2—C6	1.438 (2)	C14—C17	1.504 (3)
N2—C7	1.476 (2)	C14—C16	1.507 (3)
N2—C10	1.472 (2)	C14—C15	1.509 (3)
C1—C2	1.382 (3)	C4—H4	0.9300
C1—C6	1.407 (2)	C12—H12	0.9300
O1—C13	1.207 (2)	C15—H15A	0.9600
C6—C5	1.392 (3)	C15—H15B	0.9600
C2—C3	1.384 (3)	C15—H15C	0.9600
C2—H2	0.9300	C9—H9	0.9300
C11—C12	1.170 (3)	C16—H16A	0.9600
C11—C10	1.459 (3)	C16—H16B	0.9600
C5—C4	1.374 (3)	C16—H16C	0.9600
C5—H5	0.9300	C17—H17A	0.9600
C10—H10A	0.9700	C17—H17B	0.9600
C10—H10B	0.9700	C17—H17C	0.9600
C8—C9	1.164 (3)
C13—N1—C1	128.60 (16)	C8—C7—H7A	108.7
C13—N1—HN1	118.4 (14)	N2—C7—H7A	108.7
C1—N1—HN1	113.0 (14)	C8—C7—H7B	108.7
C13—O2—C14	122.13 (14)	N2—C7—H7B	108.7
C6—N2—C7	114.07 (15)	H7A—C7—H7B	107.6
C6—N2—C10	113.60 (15)	O2—C14—C17	110.24 (16)
C7—N2—C10	112.31 (14)	O2—C14—C16	109.50 (18)
C2—C1—C6	119.35 (16)	C17—C14—C16	112.2 (2)
C2—C1—N1	124.15 (16)	O2—C14—C15	102.07 (16)
C6—C1—N1	116.50 (16)	C17—C14—C15	111.9 (2)
O1—C13—O2	125.71 (16)	C16—C14—C15	110.5 (2)
O1—C13—N1	125.54 (17)	C5—C4—C3	119.92 (19)
O2—C13—N1	108.74 (15)	C5—C4—H4	120.0
C5—C6—C1	118.91 (18)	C3—C4—H4	120.0
C5—C6—N2	123.34 (16)	C11—C12—H12	180.0
C1—C6—N2	117.72 (15)	C14—C15—H15A	109.5
C3—C2—C1	120.53 (18)	C14—C15—H15B	109.5
C3—C2—H2	119.7	H15A—C15—H15B	109.5
C1—C2—H2	119.7	C14—C15—H15C	109.5
C12—C11—C10	176.5 (2)	H15A—C15—H15C	109.5
C4—C5—C6	120.96 (19)	H15B—C15—H15C	109.5
C4—C5—H5	119.5	C8—C9—H9	180.0
C6—C5—H5	119.5	C14—C16—H16A	109.5
C11—C10—N2	111.90 (16)	C14—C16—H16B	109.5
C11—C10—H10A	109.2	H16A—C16—H16B	109.5
N2—C10—H10A	109.2	C14—C16—H16C	109.5
C11—C10—H10B	109.2	H16A—C16—H16C	109.5
N2—C10—H10B	109.2	H16B—C16—H16C	109.5
H10A—C10—H10B	107.9	C14—C17—H17A	109.5
C9—C8—C7	177.1 (3)	C14—C17—H17B	109.5
C4—C3—C2	120.3 (2)	H17A—C17—H17B	109.5
C4—C3—H3	119.8	C14—C17—H17C	109.5
C2—C3—H3	119.8	H17A—C17—H17C	109.5
C8—C7—N2	114.21 (17)	H17B—C17—H17C	109.5
C13—N1—C1—C2	10.1 (3)	N1—C1—C2—C3	178.67 (18)
C13—N1—C1—C6	−170.50 (17)	C1—C6—C5—C4	0.4 (3)
C14—O2—C13—O1	5.5 (3)	N2—C6—C5—C4	−177.51 (18)
C14—O2—C13—N1	−173.54 (16)	C12—C11—C10—N2	−149 (4)
C1—N1—C13—O1	−2.8 (3)	C6—N2—C10—C11	157.11 (15)
C1—N1—C13—O2	176.26 (16)	C7—N2—C10—C11	−71.6 (2)
C2—C1—C6—C5	0.5 (3)	C1—C2—C3—C4	0.0 (3)
N1—C1—C6—C5	−178.92 (16)	C9—C8—C7—N2	46 (6)
C2—C1—C6—N2	178.52 (16)	C6—N2—C7—C8	70.5 (2)
N1—C1—C6—N2	−0.9 (2)	C10—N2—C7—C8	−60.6 (2)
C7—N2—C6—C5	−96.4 (2)	C13—O2—C14—C17	57.2 (3)
C10—N2—C6—C5	34.0 (2)	C13—O2—C14—C16	−66.8 (2)
C7—N2—C6—C1	85.68 (18)	C13—O2—C14—C15	176.18 (18)
C10—N2—C6—C1	−143.86 (16)	C6—C5—C4—C3	−1.1 (3)
C6—C1—C2—C3	−0.7 (3)	C2—C3—C4—C5	0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1i	0.97	2.55	3.512 (2)	171
C9—H9···O1ii	0.93	2.28	3.194 (3)	166
C2—H2···O1	0.93	2.32	2.911 (3)	121
N1—HN1···N2	0.810 (19)	2.28 (2)	2.703 (2)	114 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1i	0.97	2.55	3.512 (2)	171
C9—H9⋯O1ii	0.93	2.28	3.194 (3)	166
C2—H2⋯O1	0.93	2.32	2.911 (3)	121
N1—HN1⋯N2	0.810 (19)	2.28 (2)	2.703 (2)	114 (2)

Symmetry codes: (i) ; (ii) .