N-Cyclo-pentyl-3-(4-hydr-oxy-6-oxo-1,6-dihydro-pyrimidin-5-yl)-3-p-tolyl-propanamide.

In the mol-ecule of the title compound, C(19)H(23)N(3)O(3), the six-membered rings are oriented at a dihedral angle of 73.06 (3)°. The cyclo-pentyl ring adopts an envelope conformation. In the crystal structure, inter-molecular N-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules. In the tolyl ring, the H atoms and all but one of the C atoms are disordered over two positions and were refined with occupancies of 0.51 (3) and 0.49 (3).

Related literature

For general background, see: Johar et al. (2005 ▶); Janeba et al. (2005 ▶); Soloducho et al. (2003 ▶); Mathews & Asokan (2007 ▶); Lagoja (2005 ▶); Michael (2005 ▶); Erian (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H23N3O3

M = 341.40

Monoclinic,

a = 11.6798 (10) Å

b = 14.8279 (16) Å

c = 11.8422 (12) Å

β = 115.022 (2)°

V = 1858.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.40 × 0.38 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.967, T max = 0.981

9104 measured reflections

3262 independent reflections

1965 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.130

S = 1.03

3262 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536809001391/hk2612sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001391/hk2612Isup2.hkl

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

C19H23N3O3	F(000) = 728
Mr = 341.40	Dx = 1.220 Mg m−3
Monoclinic, P21/c	Melting point = 547–549 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.6798 (10) Å	Cell parameters from 2142 reflections
b = 14.8279 (16) Å	θ = 2.4–25.3°
c = 11.8422 (12) Å	µ = 0.08 mm−1
β = 115.022 (2)°	T = 298 K
V = 1858.4 (3) Å3	Block, colorless
Z = 4	0.40 × 0.38 × 0.23 mm

Bruker SMART CCD area-detector diffractometer	3262 independent reflections
Radiation source: fine-focus sealed tube	1965 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→13
Tmin = 0.967, Tmax = 0.981	k = −17→9
9104 measured reflections	l = −14→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0557P)2 + 0.3901P] where P = (Fo2 + 2Fc2)/3
3262 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.21 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	Occ. (<1)
O1	0.51033 (15)	0.18524 (10)	0.24325 (14)	0.0478 (4)
O2	0.58111 (16)	0.48802 (10)	0.17050 (14)	0.0519 (5)
H2	0.5650	0.5192	0.1084	0.078*
O3	0.36199 (16)	0.38438 (11)	0.37082 (15)	0.0565 (5)
N1	0.45054 (17)	0.24273 (12)	0.04951 (16)	0.0415 (5)
H1	0.4223	0.1907	0.0181	0.050*
N2	0.47888 (17)	0.39142 (12)	0.00944 (16)	0.0407 (5)
N3	0.36553 (17)	0.50839 (13)	0.26475 (16)	0.0436 (5)
H3	0.4105	0.5496	0.2520	0.052*
C1	0.5061 (2)	0.25152 (15)	0.1789 (2)	0.0366 (5)
C2	0.5537 (2)	0.33982 (14)	0.22258 (19)	0.0348 (5)
C3	0.5389 (2)	0.40604 (15)	0.13651 (19)	0.0369 (5)
C4	0.4392 (2)	0.31040 (16)	−0.0272 (2)	0.0430 (6)
H4	0.4004	0.2992	−0.1125	0.052*
C5	0.4234 (2)	0.44262 (15)	0.3448 (2)	0.0414 (6)
C6	0.5653 (2)	0.44127 (15)	0.4011 (2)	0.0433 (6)
H6A	0.5977	0.4429	0.4912	0.052*
H6B	0.5957	0.4945	0.3746	0.052*
C7	0.6153 (2)	0.35575 (14)	0.36151 (19)	0.0385 (5)
H7	0.5905	0.3047	0.3988	0.046*
C8	0.7589 (2)	0.35570 (16)	0.4198 (2)	0.0493 (6)
C9	0.822 (3)	0.3612 (18)	0.342 (3)	0.059 (4)	0.51 (3)
H9	0.7759	0.3626	0.2559	0.071*	0.51 (3)
C9'	0.838 (3)	0.382 (2)	0.370 (3)	0.069 (5)	0.49 (3)
H9'	0.8043	0.4040	0.2884	0.082*	0.49 (3)
C10	0.952 (3)	0.3646 (19)	0.392 (3)	0.074 (4)	0.51 (3)
H10	0.9918	0.3698	0.3383	0.089*	0.51 (3)
C10'	0.970 (3)	0.377 (2)	0.437 (2)	0.083 (6)	0.49 (3)
H10'	1.0222	0.3923	0.3991	0.100*	0.49 (3)
C11	1.025 (4)	0.361 (2)	0.517 (3)	0.072 (6)	0.51 (3)
C11'	1.023 (4)	0.350 (3)	0.561 (3)	0.080 (8)	0.49 (3)
C12	0.964 (2)	0.3535 (19)	0.596 (2)	0.082 (5)	0.51 (3)
H12	1.0112	0.3506	0.6818	0.098*	0.51 (3)
C12'	0.943 (3)	0.3240 (16)	0.611 (2)	0.084 (5)	0.49 (3)
H12'	0.9764	0.3037	0.6925	0.101*	0.49 (3)
C13	0.833 (4)	0.351 (2)	0.545 (4)	0.070 (6)	0.51 (3)
H13	0.7942	0.3453	0.5991	0.084*	0.51 (3)
C13'	0.813 (4)	0.327 (2)	0.544 (4)	0.070 (5)	0.49 (3)
H13'	0.7611	0.3088	0.5821	0.084*	0.49 (3)
C14	1.1676 (18)	0.3628 (15)	0.573 (2)	0.110 (5)	0.51 (3)
H14A	1.1995	0.3023	0.5824	0.164*	0.51 (3)
H14B	1.1991	0.3914	0.6534	0.164*	0.51 (3)
H14C	1.1948	0.3960	0.5194	0.164*	0.51 (3)
C14'	1.1691 (19)	0.3465 (18)	0.635 (2)	0.121 (7)	0.49 (3)
H14D	1.1905	0.3341	0.7209	0.181*	0.49 (3)
H14E	1.2045	0.4035	0.6277	0.181*	0.49 (3)
H14F	1.2024	0.2998	0.6011	0.181*	0.49 (3)
C15	0.2281 (2)	0.51310 (17)	0.1977 (2)	0.0539 (7)
H15	0.1881	0.5034	0.2546	0.065*
C16	0.1793 (3)	0.4455 (2)	0.0910 (3)	0.0839 (10)
H16A	0.2334	0.3927	0.1108	0.101*
H16B	0.0941	0.4264	0.0743	0.101*
C17	0.1810 (3)	0.4946 (3)	−0.0198 (3)	0.1004 (12)
H17A	0.2484	0.4714	−0.0390	0.121*
H17B	0.1014	0.4860	−0.0921	0.121*
C18	0.2015 (3)	0.5919 (3)	0.0119 (3)	0.0961 (12)
H18A	0.1392	0.6282	−0.0534	0.115*
H18B	0.2851	0.6103	0.0221	0.115*
C19	0.1885 (3)	0.60299 (19)	0.1318 (3)	0.0689 (8)
H19A	0.1018	0.6169	0.1158	0.083*
H19B	0.2428	0.6510	0.1816	0.083*

	U11	U22	U33	U12	U13	U23
N1	0.0550 (12)	0.0301 (10)	0.0396 (11)	−0.0049 (9)	0.0201 (9)	−0.0058 (9)
N2	0.0532 (12)	0.0373 (11)	0.0322 (10)	−0.0031 (9)	0.0187 (9)	−0.0019 (8)
N3	0.0434 (12)	0.0401 (11)	0.0451 (11)	0.0029 (9)	0.0167 (9)	0.0092 (9)
O1	0.0608 (11)	0.0341 (9)	0.0479 (10)	0.0002 (8)	0.0222 (8)	0.0041 (7)
O2	0.0760 (12)	0.0353 (9)	0.0387 (9)	−0.0096 (8)	0.0189 (8)	0.0005 (7)
O3	0.0634 (12)	0.0471 (10)	0.0624 (11)	0.0063 (9)	0.0300 (9)	0.0180 (9)
C1	0.0384 (13)	0.0360 (13)	0.0370 (13)	0.0040 (10)	0.0176 (10)	−0.0014 (10)
C2	0.0396 (13)	0.0326 (12)	0.0320 (12)	0.0015 (10)	0.0150 (10)	−0.0005 (10)
C3	0.0435 (13)	0.0342 (13)	0.0324 (13)	−0.0015 (10)	0.0155 (11)	−0.0039 (10)
C4	0.0534 (15)	0.0426 (15)	0.0342 (13)	−0.0021 (12)	0.0196 (11)	−0.0062 (11)
C5	0.0538 (15)	0.0362 (13)	0.0349 (13)	0.0062 (12)	0.0195 (11)	−0.0003 (11)
C6	0.0509 (15)	0.0420 (14)	0.0310 (12)	0.0038 (11)	0.0114 (11)	−0.0028 (10)
C7	0.0445 (14)	0.0340 (12)	0.0323 (12)	0.0025 (10)	0.0116 (10)	0.0012 (10)
C8	0.0484 (15)	0.0392 (14)	0.0495 (16)	0.0021 (12)	0.0102 (13)	−0.0047 (12)
C9	0.041 (8)	0.064 (9)	0.064 (9)	−0.007 (6)	0.014 (7)	−0.012 (6)
C9'	0.049 (7)	0.076 (14)	0.062 (11)	−0.009 (9)	0.007 (8)	0.001 (7)
C10	0.047 (9)	0.092 (9)	0.070 (13)	−0.004 (6)	0.013 (10)	−0.010 (8)
C10'	0.047 (10)	0.108 (12)	0.074 (19)	−0.011 (7)	0.006 (12)	−0.012 (11)
C11	0.050 (8)	0.084 (9)	0.067 (18)	−0.003 (6)	0.009 (12)	0.005 (13)
C11'	0.054 (10)	0.090 (13)	0.071 (18)	0.006 (10)	0.003 (12)	−0.003 (12)
C12	0.054 (10)	0.097 (14)	0.068 (9)	−0.011 (10)	0.000 (7)	−0.004 (8)
C12'	0.058 (10)	0.081 (11)	0.078 (7)	−0.006 (7)	−0.007 (6)	0.014 (7)
C13	0.054 (12)	0.078 (15)	0.057 (6)	−0.006 (9)	0.003 (7)	−0.004 (10)
C13'	0.054 (12)	0.078 (15)	0.058 (6)	−0.006 (9)	0.003 (7)	−0.003 (10)
C14	0.056 (5)	0.126 (9)	0.106 (13)	0.000 (5)	−0.005 (9)	0.007 (10)
C14'	0.054 (5)	0.150 (14)	0.112 (13)	0.000 (7)	−0.010 (10)	−0.010 (12)
C15	0.0443 (15)	0.0508 (16)	0.0633 (17)	0.0038 (12)	0.0195 (13)	0.0137 (13)
C16	0.0547 (19)	0.068 (2)	0.097 (3)	−0.0028 (16)	0.0014 (17)	−0.0018 (19)
C17	0.084 (3)	0.133 (4)	0.082 (3)	0.023 (2)	0.033 (2)	−0.003 (2)
C18	0.077 (2)	0.119 (3)	0.078 (2)	−0.004 (2)	0.0194 (19)	0.036 (2)
C19	0.0533 (17)	0.0587 (18)	0.083 (2)	0.0101 (14)	0.0174 (15)	0.0209 (16)

O1—C1	1.232 (2)	C12—C13	1.39 (5)
O2—C3	1.310 (2)	C12—H12	0.9300
O2—H2	0.8200	C13—H13	0.9300
O3—C5	1.242 (3)	C14—H14A	0.9600
N1—C4	1.322 (3)	C14—H14B	0.9600
N1—C1	1.395 (3)	C14—H14C	0.9600
N1—H1	0.8600	C9'—C10'	1.41 (5)
N2—C4	1.295 (3)	C9'—H9'	0.9300
N2—C3	1.382 (3)	C10'—C11'	1.38 (3)
N3—C5	1.328 (3)	C10'—H10'	0.9300
N3—C15	1.460 (3)	C11'—C12'	1.35 (4)
N3—H3	0.8600	C11'—C14'	1.56 (4)
C1—C2	1.431 (3)	C12'—C13'	1.38 (6)
C2—C3	1.373 (3)	C12'—H12'	0.9300
C2—C7	1.510 (3)	C13'—H13'	0.9300
C4—H4	0.9300	C14'—H14D	0.9600
C5—C6	1.503 (3)	C14'—H14E	0.9600
C6—C7	1.549 (3)	C14'—H14F	0.9600
C6—H6A	0.9700	C15—C19	1.515 (3)
C6—H6B	0.9700	C15—C16	1.523 (4)
C7—C8	1.520 (3)	C15—H15	0.9800
C7—H7	0.9800	C16—C17	1.509 (5)
C8—C9'	1.35 (4)	C16—H16A	0.9700
C8—C13	1.37 (4)	C16—H16B	0.9700
C8—C13'	1.40 (4)	C17—C18	1.485 (5)
C8—C9	1.41 (3)	C17—H17A	0.9700
C9—C10	1.38 (5)	C17—H17B	0.9700
C9—H9	0.9300	C18—C19	1.500 (4)
C10—C11	1.37 (3)	C18—H18A	0.9700
C10—H10	0.9300	C18—H18B	0.9700
C11—C12	1.39 (4)	C19—H19A	0.9700
C11—C14	1.51 (4)	C19—H19B	0.9700
C3—O2—H2	109.5	C11—C14—H14A	109.5
C4—N1—C1	123.31 (19)	C11—C14—H14B	109.5
C4—N1—H1	118.3	H14A—C14—H14B	109.5
C1—N1—H1	118.3	C11—C14—H14C	109.5
C4—N2—C3	117.10 (19)	H14A—C14—H14C	109.5
C5—N3—C15	122.2 (2)	H14B—C14—H14C	109.5
C5—N3—H3	118.9	C8—C9'—C10'	121 (3)
C15—N3—H3	118.9	C8—C9'—H9'	119.3
O1—C1—N1	118.9 (2)	C10'—C9'—H9'	119.3
O1—C1—C2	126.8 (2)	C11'—C10'—C9'	121 (3)
N1—C1—C2	114.31 (19)	C11'—C10'—H10'	119.7
C3—C2—C1	118.59 (19)	C9'—C10'—H10'	119.7
C3—C2—C7	123.34 (18)	C12'—C11'—C10'	118 (3)
C1—C2—C7	118.06 (18)	C12'—C11'—C14'	123 (2)
O2—C3—C2	121.54 (19)	C10'—C11'—C14'	120 (2)
O2—C3—N2	115.58 (18)	C11'—C12'—C13'	123 (3)
C2—C3—N2	122.88 (19)	C11'—C12'—H12'	118.7
N2—C4—N1	123.8 (2)	C13'—C12'—H12'	118.7
N2—C4—H4	118.1	C12'—C13'—C8	120 (3)
N1—C4—H4	118.1	C12'—C13'—H13'	119.9
O3—C5—N3	121.0 (2)	C8—C13'—H13'	119.9
O3—C5—C6	121.7 (2)	C11'—C14'—H14D	109.5
N3—C5—C6	117.3 (2)	C11'—C14'—H14E	109.5
C5—C6—C7	111.29 (18)	H14D—C14'—H14E	109.5
C5—C6—H6A	109.4	C11'—C14'—H14F	109.5
C7—C6—H6A	109.4	H14D—C14'—H14F	109.5
C5—C6—H6B	109.4	H14E—C14'—H14F	109.5
C7—C6—H6B	109.4	N3—C15—C19	110.4 (2)
H6A—C6—H6B	108.0	N3—C15—C16	111.1 (2)
C2—C7—C8	114.88 (19)	C19—C15—C16	103.1 (2)
C2—C7—C6	112.99 (17)	N3—C15—H15	110.7
C8—C7—C6	110.36 (18)	C19—C15—H15	110.7
C2—C7—H7	105.9	C16—C15—H15	110.7
C8—C7—H7	105.9	C17—C16—C15	105.4 (3)
C6—C7—H7	105.9	C17—C16—H16A	110.7
C9'—C8—C13	104.8 (18)	C15—C16—H16A	110.7
C9'—C8—C13'	118 (2)	C17—C16—H16B	110.7
C13—C8—C9	116 (2)	C15—C16—H16B	110.7
C13'—C8—C9	125 (2)	H16A—C16—H16B	108.8
C9'—C8—C7	129.0 (14)	C18—C17—C16	108.0 (3)
C13—C8—C7	124.3 (17)	C18—C17—H17A	110.1
C13'—C8—C7	113.3 (17)	C16—C17—H17A	110.1
C9—C8—C7	119.2 (12)	C18—C17—H17B	110.1
C10—C9—C8	121 (2)	C16—C17—H17B	110.1
C10—C9—H9	119.6	H17A—C17—H17B	108.4
C8—C9—H9	119.6	C17—C18—C19	106.0 (3)
C11—C10—C9	122 (3)	C17—C18—H18A	110.5
C11—C10—H10	119.0	C19—C18—H18A	110.5
C9—C10—H10	119.0	C17—C18—H18B	110.5
C10—C11—C12	118 (3)	C19—C18—H18B	110.5
C10—C11—C14	123 (3)	H18A—C18—H18B	108.7
C12—C11—C14	119 (2)	C18—C19—C15	105.1 (3)
C13—C12—C11	120 (3)	C18—C19—H19A	110.7
C13—C12—H12	120.1	C15—C19—H19A	110.7
C11—C12—H12	120.1	C18—C19—H19B	110.7
C8—C13—C12	123 (3)	C15—C19—H19B	110.7
C8—C13—H13	118.5	H19A—C19—H19B	108.8
C12—C13—H13	118.5
C4—N1—C1—O1	178.5 (2)	C7—C8—C9—C10	177.6 (19)
C4—N1—C1—C2	−1.8 (3)	C8—C9—C10—C11	2(4)
O1—C1—C2—C3	−179.2 (2)	C9—C10—C11—C12	0(5)
N1—C1—C2—C3	1.2 (3)	C9—C10—C11—C14	179 (3)
O1—C1—C2—C7	−0.4 (3)	C10—C11—C12—C13	0(5)
N1—C1—C2—C7	179.93 (18)	C14—C11—C12—C13	−180 (3)
C1—C2—C3—O2	−179.52 (19)	C9'—C8—C13—C12	−13 (3)
C7—C2—C3—O2	1.8 (3)	C13'—C8—C13—C12	126 (14)
C1—C2—C3—N2	0.7 (3)	C9—C8—C13—C12	2(4)
C7—C2—C3—N2	−178.0 (2)	C7—C8—C13—C12	−178 (2)
C4—N2—C3—O2	178.1 (2)	C11—C12—C13—C8	−1(5)
C4—N2—C3—C2	−2.1 (3)	C13—C8—C9'—C10'	16 (3)
C3—N2—C4—N1	1.5 (3)	C13'—C8—C9'—C10'	3(3)
C1—N1—C4—N2	0.5 (3)	C9—C8—C9'—C10'	−118 (10)
C15—N3—C5—O3	−3.8 (3)	C7—C8—C9'—C10'	−179.8 (17)
C15—N3—C5—C6	175.70 (19)	C8—C9'—C10'—C11'	−4(5)
O3—C5—C6—C7	63.5 (3)	C9'—C10'—C11'—C12'	4(5)
N3—C5—C6—C7	−115.9 (2)	C9'—C10'—C11'—C14'	−179 (2)
C3—C2—C7—C8	−80.4 (3)	C10'—C11'—C12'—C13'	−2(5)
C1—C2—C7—C8	100.9 (2)	C14'—C11'—C12'—C13'	−179 (3)
C3—C2—C7—C6	47.4 (3)	C11'—C12'—C13'—C8	1(5)
C1—C2—C7—C6	−131.3 (2)	C9'—C8—C13'—C12'	−1(4)
C5—C6—C7—C2	50.0 (2)	C13—C8—C13'—C12'	−47 (10)
C5—C6—C7—C8	−179.86 (19)	C9—C8—C13'—C12'	18 (4)
C2—C7—C8—C9'	31.9 (16)	C7—C8—C13'—C12'	−179 (2)
C6—C7—C8—C9'	−97.3 (16)	C5—N3—C15—C19	169.8 (2)
C2—C7—C8—C13	−166.3 (17)	C5—N3—C15—C16	−76.5 (3)
C6—C7—C8—C13	64.5 (18)	N3—C15—C16—C17	−89.0 (3)
C2—C7—C8—C13'	−150.5 (16)	C19—C15—C16—C17	29.2 (3)
C6—C7—C8—C13'	80.4 (16)	C15—C16—C17—C18	−12.2 (4)
C2—C7—C8—C9	13.8 (13)	C16—C17—C18—C19	−10.0 (4)
C6—C7—C8—C9	−115.4 (13)	C17—C18—C19—C15	28.6 (3)
C9'—C8—C9—C10	50 (8)	N3—C15—C19—C18	83.0 (3)
C13—C8—C9—C10	−2(3)	C16—C15—C19—C18	−35.7 (3)
C13'—C8—C9—C10	−20 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	1.93	2.692 (3)	147
O2—H2···N2ii	0.82	1.83	2.639 (3)	167
N3—H3···O1iii	0.86	2.20	3.017 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	1.93	2.692 (3)	147
O2—H2⋯N2ii	0.82	1.83	2.639 (3)	167
N3—H3⋯O1iii	0.86	2.20	3.017 (3)	158

Symmetry codes: (i) ; (ii) ; (iii) .