2-[(Phenyl-carbamo-yl)amino]-butyl N-phenyl-carbamate.

In the title compound, C(18)H(21)N(3)O(3), the terminal phenyl rings make a dihedral angle of 86.3 (5)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into chains along [001], forming parallel C(4) and R(1) (2)(6) graph-set motifs.

Related literature

For pharmaceutical properties of carbamates and carbamide compounds, see: Li et al. (2009 ▶); Gisbert & Pajares (2004 ▶); Metcalf (2002 ▶); Ray & Chaturvedi (2004 ▶). For a related structure, see: Ghalib et al. (2010 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H21N3O3

M = 327.38

Monoclinic,

a = 10.722 (5) Å

b = 22.297 (3) Å

c = 9.109 (3) Å

β = 123.570 (6)°

V = 1814.5 (11) Å3

Z = 4

Cu Kα radiation

μ = 0.68 mm−1

T = 293 K

0.14 × 0.12 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer

2915 measured reflections

1676 independent reflections

1264 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.155

S = 1.05

1676 reflections

231 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.22 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038081/hg5248sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038081/hg5248Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038081/hg5248Isup3.cml

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

C18H21N3O3	F(000) = 696
Mr = 327.38	Dx = 1.198 Mg m−3
Monoclinic, Cc	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: C -2yc	Cell parameters from 838 reflections
a = 10.722 (5) Å	θ = 4.0–72.5°
b = 22.297 (3) Å	µ = 0.68 mm−1
c = 9.109 (3) Å	T = 293 K
β = 123.570 (6)°	Plate, colourless
V = 1814.5 (11) Å3	0.14 × 0.12 × 0.07 mm
Z = 4

Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer	1264 reflections with I > 2σ(I)
Radiation source: Enhance (Cu) X-ray Source	Rint = 0.024
Graphite monochromator	θmax = 72.7°, θmin = 4.0°
Detector resolution: 16.3280 pixels mm-1	h = −10→13
ω scans	k = −26→27
2915 measured reflections	l = −11→8
1676 independent 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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0822P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1676 reflections	Δρmax = 0.22 e Å−3
231 parameters	Δρmin = −0.22 e Å−3
5 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: 0.0019 (5)

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 F2 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 F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.2114 (5)	0.75128 (17)	0.7981 (6)	0.1177 (16)
O2	−0.0009 (4)	0.69881 (13)	0.6486 (4)	0.0788 (10)
O3	0.0605 (5)	0.51102 (14)	0.6398 (5)	0.0941 (16)
N1	0.0064 (5)	0.78786 (17)	0.5510 (5)	0.0734 (14)
N2	0.0156 (6)	0.55146 (15)	0.8323 (5)	0.0847 (18)
N3	0.1249 (6)	0.45933 (16)	0.8872 (6)	0.0886 (18)
C1	0.0557 (6)	0.84566 (19)	0.5415 (6)	0.0722 (16)
C2	−0.0217 (7)	0.8733 (2)	0.3778 (8)	0.092 (2)
C3	0.0180 (10)	0.9309 (3)	0.3609 (11)	0.124 (3)
C4	0.1309 (10)	0.9615 (3)	0.5060 (12)	0.123 (3)
C5	0.2039 (8)	0.9341 (3)	0.6652 (11)	0.110 (3)
C6	0.1700 (7)	0.8764 (2)	0.6871 (8)	0.088 (2)
C7	0.0846 (6)	0.74643 (18)	0.6781 (6)	0.0704 (16)
C8	0.0670 (7)	0.6502 (2)	0.7745 (7)	0.0822 (18)
C9	−0.0553 (6)	0.60516 (19)	0.7281 (6)	0.0797 (18)
C10	−0.1753 (9)	0.6283 (3)	0.7544 (10)	0.111 (3)
C11	−0.1308 (16)	0.6430 (4)	0.9279 (16)	0.182 (6)
C12	0.0681 (6)	0.50769 (18)	0.7795 (6)	0.0771 (18)
C13	0.1897 (7)	0.4088 (2)	0.8611 (7)	0.088 (2)
C14	0.1571 (11)	0.3526 (2)	0.8931 (10)	0.120 (3)
C15	0.2259 (17)	0.3026 (3)	0.8774 (17)	0.180 (6)
C16	0.3162 (16)	0.3086 (4)	0.8189 (17)	0.184 (7)
C17	0.3521 (12)	0.3633 (3)	0.7913 (13)	0.151 (5)
C18	0.2891 (9)	0.4141 (3)	0.8129 (10)	0.111 (3)
H1N	−0.085 (3)	0.778 (2)	0.472 (5)	0.087 (17)*
H2	−0.09950	0.85340	0.28010	0.1110*
H2N	0.020 (5)	0.549 (2)	0.929 (4)	0.072 (13)*
H3	−0.03200	0.94910	0.25070	0.1480*
H3N	0.092 (6)	0.456 (2)	0.954 (6)	0.087 (15)*
H4	0.15640	1.00020	0.49460	0.1470*
H5	0.27940	0.95480	0.76300	0.1320*
H6	0.22280	0.85830	0.79760	0.1050*
H8A	0.11030	0.66520	0.89320	0.0990*
H8B	0.14570	0.63160	0.76810	0.0990*
H9	−0.10400	0.59450	0.60360	0.0950*
H10A	−0.21960	0.66380	0.68200	0.1330*
H10B	−0.25340	0.59820	0.70980	0.1330*
H11A	−0.20880	0.66540	0.92430	0.2720*
H11B	−0.04100	0.66660	0.98310	0.2720*
H11C	−0.11230	0.60680	0.99410	0.2720*
H14	0.08890	0.34810	0.92510	0.1440*
H15	0.20950	0.26490	0.90750	0.2150*
H16	0.35410	0.27460	0.79740	0.2200*
H17	0.41930	0.36720	0.75760	0.1800*
H18	0.31480	0.45190	0.79440	0.1320*

	U11	U22	U33	U12	U13	U23
O1	0.073 (3)	0.078 (2)	0.119 (3)	−0.0025 (17)	0.001 (3)	0.014 (2)
O2	0.086 (2)	0.0655 (16)	0.0737 (18)	−0.0028 (14)	0.0372 (17)	0.0139 (14)
O3	0.176 (4)	0.0685 (17)	0.094 (2)	0.005 (2)	0.110 (3)	0.0044 (16)
N1	0.077 (3)	0.0649 (19)	0.074 (2)	−0.0062 (17)	0.039 (2)	0.0022 (17)
N2	0.159 (4)	0.0572 (18)	0.085 (3)	0.016 (2)	0.097 (3)	0.0076 (18)
N3	0.161 (4)	0.0644 (19)	0.095 (3)	0.021 (2)	0.105 (3)	0.0121 (18)
C1	0.089 (3)	0.060 (2)	0.085 (3)	−0.001 (2)	0.059 (3)	0.006 (2)
C2	0.110 (4)	0.074 (3)	0.099 (4)	0.002 (3)	0.062 (3)	0.014 (3)
C3	0.177 (7)	0.081 (3)	0.127 (5)	0.003 (4)	0.092 (6)	0.027 (4)
C4	0.161 (7)	0.070 (3)	0.159 (7)	−0.015 (4)	0.102 (6)	0.009 (4)
C5	0.131 (5)	0.071 (3)	0.141 (6)	−0.023 (3)	0.083 (5)	−0.016 (4)
C6	0.101 (4)	0.072 (3)	0.097 (4)	−0.016 (3)	0.059 (3)	−0.010 (3)
C7	0.081 (3)	0.052 (2)	0.076 (3)	0.0030 (19)	0.042 (3)	0.0076 (18)
C8	0.109 (4)	0.062 (2)	0.081 (3)	0.010 (2)	0.056 (3)	0.016 (2)
C9	0.124 (4)	0.057 (2)	0.081 (3)	0.007 (2)	0.071 (3)	0.0054 (19)
C10	0.150 (6)	0.079 (3)	0.145 (6)	0.008 (4)	0.108 (5)	0.010 (3)
C11	0.284 (13)	0.146 (8)	0.215 (10)	0.065 (8)	0.201 (11)	0.031 (7)
C12	0.135 (4)	0.053 (2)	0.086 (3)	0.003 (2)	0.088 (3)	0.0014 (19)
C13	0.144 (5)	0.066 (2)	0.096 (3)	0.019 (3)	0.092 (4)	0.006 (2)
C14	0.218 (8)	0.068 (3)	0.147 (5)	0.020 (4)	0.146 (6)	0.015 (3)
C15	0.345 (14)	0.071 (4)	0.246 (11)	0.052 (6)	0.241 (12)	0.034 (5)
C16	0.322 (15)	0.093 (5)	0.268 (13)	0.075 (7)	0.246 (13)	0.041 (6)
C17	0.228 (10)	0.113 (5)	0.204 (9)	0.051 (6)	0.178 (9)	0.020 (5)
C18	0.165 (6)	0.085 (3)	0.141 (5)	0.015 (4)	0.122 (5)	0.002 (3)

O1—C7	1.188 (8)	C13—C14	1.375 (8)
O2—C7	1.330 (6)	C14—C15	1.387 (16)
O2—C8	1.448 (6)	C15—C16	1.35 (3)
O3—C12	1.232 (7)	C16—C17	1.344 (14)
N1—C1	1.414 (6)	C17—C18	1.387 (13)
N1—C7	1.350 (6)	C2—H2	0.9300
N2—C9	1.454 (6)	C3—H3	0.9300
N2—C12	1.342 (7)	C4—H4	0.9300
N3—C12	1.355 (6)	C5—H5	0.9300
N3—C13	1.411 (8)	C6—H6	0.9300
N1—H1N	0.86 (4)	C8—H8A	0.9700
N2—H2N	0.86 (4)	C8—H8B	0.9700
N3—H3N	0.86 (6)	C9—H9	0.9800
C1—C6	1.390 (8)	C10—H10A	0.9700
C1—C2	1.387 (7)	C10—H10B	0.9700
C2—C3	1.388 (9)	C11—H11A	0.9600
C3—C4	1.381 (12)	C11—H11B	0.9600
C4—C5	1.354 (12)	C11—H11C	0.9600
C5—C6	1.381 (9)	C14—H14	0.9300
C8—C9	1.515 (9)	C15—H15	0.9300
C9—C10	1.523 (12)	C16—H16	0.9300
C10—C11	1.414 (15)	C17—H17	0.9300
C13—C18	1.364 (13)	C18—H18	0.9300
C7—O2—C8	116.7 (4)	C3—C2—H2	120.00
C1—N1—C7	126.9 (5)	C2—C3—H3	120.00
C9—N2—C12	122.5 (4)	C4—C3—H3	120.00
C12—N3—C13	125.4 (5)	C3—C4—H4	121.00
C7—N1—H1N	115 (3)	C5—C4—H4	121.00
C1—N1—H1N	118 (3)	C4—C5—H5	119.00
C9—N2—H2N	116 (3)	C6—C5—H5	119.00
C12—N2—H2N	122 (3)	C1—C6—H6	120.00
C13—N3—H3N	119 (3)	C5—C6—H6	121.00
C12—N3—H3N	113 (3)	O2—C8—H8A	110.00
N1—C1—C6	123.6 (4)	O2—C8—H8B	110.00
C2—C1—C6	119.6 (5)	C9—C8—H8A	110.00
N1—C1—C2	116.7 (5)	C9—C8—H8B	110.00
C1—C2—C3	119.5 (6)	H8A—C8—H8B	109.00
C2—C3—C4	120.7 (7)	N2—C9—H9	108.00
C3—C4—C5	118.9 (7)	C8—C9—H9	108.00
C4—C5—C6	122.2 (7)	C10—C9—H9	108.00
C1—C6—C5	119.0 (6)	C9—C10—H10A	108.00
O2—C7—N1	110.0 (5)	C9—C10—H10B	108.00
O1—C7—O2	124.7 (4)	C11—C10—H10A	108.00
O1—C7—N1	125.4 (5)	C11—C10—H10B	108.00
O2—C8—C9	107.3 (5)	H10A—C10—H10B	107.00
N2—C9—C10	111.0 (5)	C10—C11—H11A	109.00
C8—C9—C10	114.1 (5)	C10—C11—H11B	109.00
N2—C9—C8	107.7 (5)	C10—C11—H11C	109.00
C9—C10—C11	117.5 (10)	H11A—C11—H11B	110.00
N2—C12—N3	115.4 (5)	H11A—C11—H11C	109.00
O3—C12—N3	122.9 (5)	H11B—C11—H11C	109.00
O3—C12—N2	121.7 (4)	C13—C14—H14	120.00
N3—C13—C14	119.0 (8)	C15—C14—H14	120.00
N3—C13—C18	122.0 (5)	C14—C15—H15	120.00
C14—C13—C18	118.9 (7)	C16—C15—H15	120.00
C13—C14—C15	119.9 (12)	C15—C16—H16	120.00
C14—C15—C16	120.1 (9)	C17—C16—H16	120.00
C15—C16—C17	120.5 (12)	C16—C17—H17	120.00
C16—C17—C18	120.1 (13)	C18—C17—H17	120.00
C13—C18—C17	120.2 (8)	C13—C18—H18	120.00
C1—C2—H2	120.00	C17—C18—H18	120.00
C7—O2—C8—C9	172.8 (5)	C6—C1—C2—C3	1.3 (12)
C8—O2—C7—N1	−179.8 (5)	C1—C2—C3—C4	−1.7 (15)
C8—O2—C7—O1	0.8 (9)	C2—C3—C4—C5	0.9 (17)
C1—N1—C7—O1	−4.2 (10)	C3—C4—C5—C6	0.5 (16)
C7—N1—C1—C6	−22.7 (10)	C4—C5—C6—C1	−1.0 (14)
C1—N1—C7—O2	176.3 (5)	O2—C8—C9—C10	−66.4 (6)
C7—N1—C1—C2	160.8 (6)	O2—C8—C9—N2	169.9 (4)
C12—N2—C9—C8	−86.4 (6)	C8—C9—C10—C11	−63.7 (8)
C9—N2—C12—N3	−177.1 (6)	N2—C9—C10—C11	58.2 (8)
C12—N2—C9—C10	148.1 (6)	N3—C13—C14—C15	−176.5 (8)
C9—N2—C12—O3	0.9 (10)	C18—C13—C14—C15	0.5 (12)
C13—N3—C12—N2	−178.2 (6)	N3—C13—C18—C17	179.0 (7)
C13—N3—C12—O3	3.9 (10)	C14—C13—C18—C17	2.1 (11)
C12—N3—C13—C18	44.7 (10)	C13—C14—C15—C16	−4.7 (17)
C12—N3—C13—C14	−138.4 (7)	C14—C15—C16—C17	6 (2)
N1—C1—C6—C5	−176.3 (7)	C15—C16—C17—C18	−3.9 (19)
C2—C1—C6—C5	0.1 (12)	C16—C17—C18—C13	−0.4 (14)
N1—C1—C2—C3	177.9 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (4)	1.97 (4)	2.831 (7)	175 (4)
N2—H2N···O3ii	0.86 (4)	2.18 (4)	2.920 (6)	145 (4)
N3—H3N···O3ii	0.86 (6)	2.04 (6)	2.822 (8)	152 (4)
C6—H6···O1	0.93	2.39	2.917 (6)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86 (4)	1.97 (4)	2.831 (7)	175 (4)
N2—H2N⋯O3ii	0.86 (4)	2.18 (4)	2.920 (6)	145 (4)
N3—H3N⋯O3ii	0.86 (6)	2.04 (6)	2.822 (8)	152 (4)

Symmetry codes: (i) ; (ii) .