4-[3,5-Bis(2-hy-droxy-phen-yl)-1H-1,2,4-triazol-1-yl]benzoic acid dimethyl-formamide monosolvate.

In the mol-ecule of deferasirox dimethyl-formamide solvate, C(21)H(15)N(3)O(4)·C(3)H(7)NO, the central 1,2,4-triazole ring is tilted with respect to the benzoic acid and one of the 2-hy-droxy-phenyl units but coplanar with the other 2-hy-droxy-phenyl group, as indicated by the dihedral angles of 33.69 (9), 72.57 (8) and 5.18 (9)°, respectively. Intra-molecular O-H⋯N hydrogen bonds generate an S(6) ring motif. In the crystal, deferasirox mol-ecules are linked by O-H⋯N hydrogen bonds and weak C-H⋯O inter-actions into chains along the c axis. The dimethyl-formamide solvent mol-ecules are located between the deferasirox chains and are linked to the deferasirox mol-ecules by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For graph-set notation, see Bernstein et al. (1995 ▶). For background to, and applications of, deferasirox, see: Choudhry & Naithani (2007 ▶); Lalitha Manasa et al. (2011 ▶); Nick et al. (2003 ▶); Yang et al. (2007 ▶). For related structures, see: Ishak et al. (2011 ▶); Rajnikant et al. (2006 ▶); Yathirajan et al. (2006 ▶, 2007 ▶). For the stability of the temperature controller, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H15N3O4·C3H7NO

M = 446.46

Monoclinic,

a = 8.8172 (8) Å

b = 32.669 (3) Å

c = 7.6900 (7) Å

β = 94.901 (2)°

V = 2207.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.32 × 0.25 × 0.11 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.970, T max = 0.989

18347 measured reflections

6379 independent reflections

4384 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.144

S = 1.04

6379 reflections

303 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005806/ez2281sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005806/ez2281Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005806/ez2281Isup3.cml

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

C21H15N3O4·C3H7NO	F(000) = 936
Mr = 446.46	Dx = 1.344 Mg m−3
Monoclinic, P21/c	Melting point = 539–540 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.8172 (8) Å	Cell parameters from 6379 reflections
b = 32.669 (3) Å	θ = 2.3–30.0°
c = 7.6900 (7) Å	µ = 0.10 mm−1
β = 94.901 (2)°	T = 100 K
V = 2207.0 (3) Å3	Block, colorless
Z = 4	0.32 × 0.25 × 0.11 mm

Bruker APEX DUO CCD area-detector diffractometer	6379 independent reflections
Radiation source: sealed tube	4384 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→11
Tmin = 0.970, Tmax = 0.989	k = −44→45
18347 measured reflections	l = −10→10

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0461P)2 + 1.5844P] where P = (Fo2 + 2Fc2)/3
6379 reflections	(Δ/σ)max = 0.001
303 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.33110 (15)	0.08811 (4)	1.31456 (16)	0.0238 (3)
O2	0.3878 (3)	0.02777 (5)	1.2036 (2)	0.0742 (8)
H1O2	0.3513	0.0199	1.3047	0.111*
O3	0.90883 (15)	0.10202 (5)	0.38917 (18)	0.0311 (3)
H1O3	0.830 (3)	0.1058 (8)	0.456 (3)	0.047*
O4	0.46909 (15)	0.25263 (4)	0.60966 (19)	0.0306 (3)
H1O4	0.4693	0.2783	0.6808	0.046*
O5	0.2916 (3)	−0.00057 (5)	0.4879 (2)	0.0792 (8)
N1	0.52636 (15)	0.14408 (4)	0.56919 (18)	0.0167 (3)
N2	0.64907 (15)	0.13126 (5)	0.48553 (18)	0.0198 (3)
N3	0.52841 (16)	0.18321 (4)	0.33783 (18)	0.0184 (3)
N4	0.1441 (3)	0.01691 (6)	0.7044 (2)	0.0470 (5)
C1	0.4152 (2)	0.08640 (5)	1.0291 (2)	0.0226 (4)
C2	0.4791 (3)	0.06402 (6)	0.8993 (3)	0.0371 (5)
H2A	0.4978	0.0356	0.9155	0.045*
C3	0.5156 (2)	0.08293 (6)	0.7465 (2)	0.0302 (4)
H3A	0.5586	0.0676	0.6579	0.036*
C4	0.48836 (18)	0.12443 (5)	0.7255 (2)	0.0175 (3)
C5	0.42428 (19)	0.14715 (5)	0.8531 (2)	0.0188 (3)
H5A	0.4061	0.1756	0.8371	0.023*
C6	0.38716 (18)	0.12784 (5)	1.0040 (2)	0.0176 (3)
H6A	0.3420	0.1431	1.0912	0.021*
C7	0.3750 (2)	0.06792 (5)	1.1966 (2)	0.0261 (4)
C8	0.45577 (18)	0.17495 (5)	0.4780 (2)	0.0162 (3)
C9	0.64624 (18)	0.15571 (5)	0.3471 (2)	0.0174 (3)
C10	0.75991 (18)	0.15289 (5)	0.2187 (2)	0.0194 (3)
C11	0.88427 (19)	0.12628 (6)	0.2452 (2)	0.0234 (4)
C12	0.9916 (2)	0.12447 (7)	0.1219 (3)	0.0301 (4)
H12A	1.0766	0.1066	0.1403	0.036*
C13	0.9752 (2)	0.14846 (7)	−0.0266 (3)	0.0300 (4)
H13A	1.0485	0.1469	−0.1099	0.036*
C14	0.8524 (2)	0.17481 (6)	−0.0546 (2)	0.0274 (4)
H14A	0.8409	0.1911	−0.1571	0.033*
C15	0.7463 (2)	0.17722 (6)	0.0682 (2)	0.0228 (4)
H15A	0.6631	0.1956	0.0499	0.027*
C16	0.31623 (19)	0.19581 (5)	0.5244 (2)	0.0178 (3)
C17	0.3273 (2)	0.23590 (5)	0.5890 (2)	0.0210 (3)
C18	0.1957 (2)	0.25621 (6)	0.6290 (2)	0.0247 (4)
H18A	0.2015	0.2836	0.6701	0.030*
C19	0.0568 (2)	0.23642 (6)	0.6089 (2)	0.0253 (4)
H19A	−0.0323	0.2503	0.6376	0.030*
C20	0.0455 (2)	0.19649 (6)	0.5472 (2)	0.0240 (4)
H20A	−0.0506	0.1832	0.5341	0.029*
C21	0.17560 (19)	0.17613 (5)	0.5049 (2)	0.0203 (3)
H21A	0.1687	0.1488	0.4627	0.024*
C22	0.2029 (3)	0.02297 (7)	0.5528 (3)	0.0466 (6)
H22A	0.1744	0.0472	0.4900	0.056*
C23	0.0407 (3)	0.04676 (10)	0.7700 (3)	0.0563 (7)
H23A	0.0277	0.0697	0.6882	0.085*
H23B	0.0829	0.0568	0.8841	0.085*
H23C	−0.0583	0.0339	0.7819	0.085*
C24	0.1866 (6)	−0.01805 (8)	0.8146 (4)	0.0949 (15)
H24A	0.2634	−0.0343	0.7608	0.142*
H24B	0.0965	−0.0350	0.8277	0.142*
H24C	0.2284	−0.0085	0.9295	0.142*

	U11	U22	U33	U12	U13	U23
O1	0.0325 (7)	0.0215 (6)	0.0185 (6)	0.0024 (5)	0.0092 (5)	−0.0005 (5)
O2	0.173 (2)	0.0205 (8)	0.0388 (9)	0.0265 (11)	0.0645 (12)	0.0114 (7)
O3	0.0238 (6)	0.0473 (9)	0.0231 (7)	0.0112 (6)	0.0075 (5)	0.0051 (6)
O4	0.0321 (7)	0.0239 (7)	0.0376 (8)	−0.0077 (6)	0.0132 (6)	−0.0149 (6)
O5	0.182 (2)	0.0248 (8)	0.0402 (10)	0.0076 (12)	0.0640 (13)	0.0047 (7)
N1	0.0168 (6)	0.0176 (7)	0.0166 (7)	0.0009 (5)	0.0056 (5)	0.0007 (5)
N2	0.0170 (6)	0.0253 (8)	0.0178 (7)	0.0018 (6)	0.0064 (5)	0.0001 (6)
N3	0.0219 (7)	0.0173 (7)	0.0167 (7)	−0.0017 (5)	0.0052 (5)	−0.0009 (5)
N4	0.0819 (15)	0.0402 (11)	0.0216 (9)	−0.0273 (11)	0.0198 (10)	−0.0057 (8)
C1	0.0319 (9)	0.0205 (8)	0.0167 (8)	0.0051 (7)	0.0089 (7)	0.0024 (6)
C2	0.0672 (15)	0.0212 (9)	0.0263 (10)	0.0179 (10)	0.0233 (10)	0.0075 (8)
C3	0.0477 (12)	0.0240 (9)	0.0214 (9)	0.0136 (8)	0.0182 (8)	0.0032 (7)
C4	0.0181 (7)	0.0200 (8)	0.0149 (7)	0.0009 (6)	0.0033 (6)	0.0021 (6)
C5	0.0235 (8)	0.0163 (8)	0.0168 (8)	0.0009 (6)	0.0032 (6)	−0.0006 (6)
C6	0.0198 (7)	0.0179 (8)	0.0154 (7)	0.0006 (6)	0.0037 (6)	−0.0020 (6)
C7	0.0399 (10)	0.0202 (9)	0.0197 (8)	0.0056 (8)	0.0113 (8)	0.0036 (7)
C8	0.0186 (7)	0.0147 (7)	0.0158 (7)	−0.0021 (6)	0.0037 (6)	−0.0018 (6)
C9	0.0153 (7)	0.0202 (8)	0.0170 (8)	−0.0013 (6)	0.0032 (6)	−0.0016 (6)
C10	0.0167 (7)	0.0250 (9)	0.0171 (8)	−0.0035 (6)	0.0052 (6)	−0.0031 (6)
C11	0.0191 (8)	0.0336 (10)	0.0179 (8)	−0.0009 (7)	0.0037 (6)	−0.0016 (7)
C12	0.0201 (8)	0.0467 (12)	0.0243 (9)	0.0035 (8)	0.0067 (7)	−0.0028 (8)
C13	0.0228 (9)	0.0455 (12)	0.0233 (9)	−0.0048 (8)	0.0109 (7)	−0.0042 (8)
C14	0.0284 (9)	0.0344 (10)	0.0205 (9)	−0.0069 (8)	0.0083 (7)	0.0000 (8)
C15	0.0219 (8)	0.0253 (9)	0.0219 (9)	−0.0031 (7)	0.0057 (7)	−0.0009 (7)
C16	0.0222 (8)	0.0171 (8)	0.0146 (7)	0.0029 (6)	0.0052 (6)	0.0004 (6)
C17	0.0284 (9)	0.0180 (8)	0.0177 (8)	−0.0004 (7)	0.0076 (7)	−0.0005 (6)
C18	0.0355 (10)	0.0189 (8)	0.0205 (8)	0.0063 (7)	0.0076 (7)	−0.0010 (7)
C19	0.0279 (9)	0.0282 (9)	0.0209 (8)	0.0104 (8)	0.0074 (7)	0.0011 (7)
C20	0.0217 (8)	0.0292 (10)	0.0216 (9)	0.0030 (7)	0.0053 (7)	0.0008 (7)
C21	0.0241 (8)	0.0193 (8)	0.0181 (8)	0.0009 (7)	0.0061 (7)	0.0001 (6)
C22	0.0835 (18)	0.0346 (12)	0.0241 (10)	−0.0237 (12)	0.0197 (12)	−0.0027 (9)
C23	0.0472 (14)	0.093 (2)	0.0303 (12)	−0.0088 (14)	0.0127 (11)	0.0048 (13)
C24	0.222 (5)	0.0290 (13)	0.0438 (16)	−0.011 (2)	0.069 (2)	0.0036 (11)

O1—C7	1.211 (2)	C9—C10	1.468 (2)
O2—C7	1.317 (2)	C10—C15	1.401 (2)
O2—H1O2	0.9032	C10—C11	1.401 (2)
O3—C11	1.364 (2)	C11—C12	1.397 (2)
O3—H1O3	0.91 (3)	C12—C13	1.382 (3)
O4—C17	1.361 (2)	C12—H12A	0.9500
O4—H1O4	1.0018	C13—C14	1.386 (3)
O5—C22	1.233 (3)	C13—H13A	0.9500
N1—C8	1.350 (2)	C14—C15	1.387 (2)
N1—N2	1.3707 (18)	C14—H14A	0.9500
N1—C4	1.427 (2)	C15—H15A	0.9500
N2—C9	1.329 (2)	C16—C21	1.393 (2)
N3—C8	1.327 (2)	C16—C17	1.401 (2)
N3—C9	1.371 (2)	C17—C18	1.394 (2)
N4—C22	1.331 (3)	C18—C19	1.382 (3)
N4—C24	1.452 (4)	C18—H18A	0.9500
N4—C23	1.454 (4)	C19—C20	1.389 (3)
C1—C6	1.387 (2)	C19—H19A	0.9500
C1—C2	1.394 (2)	C20—C21	1.389 (2)
C1—C7	1.493 (2)	C20—H20A	0.9500
C2—C3	1.390 (3)	C21—H21A	0.9500
C2—H2A	0.9500	C22—H22A	0.9500
C3—C4	1.384 (2)	C23—H23A	0.9800
C3—H3A	0.9500	C23—H23B	0.9800
C4—C5	1.389 (2)	C23—H23C	0.9800
C5—C6	1.384 (2)	C24—H24A	0.9800
C5—H5A	0.9500	C24—H24B	0.9800
C6—H6A	0.9500	C24—H24C	0.9800
C8—C16	1.477 (2)
C7—O2—H1O2	106.4	C13—C12—H12A	119.8
C11—O3—H1O3	107.8 (16)	C11—C12—H12A	119.8
C17—O4—H1O4	111.1	C12—C13—C14	120.40 (17)
C8—N1—N2	109.37 (13)	C12—C13—H13A	119.8
C8—N1—C4	129.99 (14)	C14—C13—H13A	119.8
N2—N1—C4	120.61 (13)	C13—C14—C15	119.53 (18)
C9—N2—N1	103.34 (13)	C13—C14—H14A	120.2
C8—N3—C9	103.93 (14)	C15—C14—H14A	120.2
C22—N4—C24	121.9 (2)	C14—C15—C10	121.02 (17)
C22—N4—C23	120.4 (2)	C14—C15—H15A	119.5
C24—N4—C23	117.6 (2)	C10—C15—H15A	119.5
C6—C1—C2	119.39 (16)	C21—C16—C17	120.27 (15)
C6—C1—C7	117.52 (15)	C21—C16—C8	120.88 (15)
C2—C1—C7	123.10 (16)	C17—C16—C8	118.85 (15)
C3—C2—C1	120.62 (17)	O4—C17—C18	123.84 (16)
C3—C2—H2A	119.7	O4—C17—C16	116.90 (15)
C1—C2—H2A	119.7	C18—C17—C16	119.26 (16)
C4—C3—C2	118.93 (17)	C19—C18—C17	119.96 (17)
C4—C3—H3A	120.5	C19—C18—H18A	120.0
C2—C3—H3A	120.5	C17—C18—H18A	120.0
C3—C4—C5	121.21 (16)	C18—C19—C20	121.00 (16)
C3—C4—N1	119.21 (15)	C18—C19—H19A	119.5
C5—C4—N1	119.58 (15)	C20—C19—H19A	119.5
C6—C5—C4	119.24 (16)	C19—C20—C21	119.54 (17)
C6—C5—H5A	120.4	C19—C20—H20A	120.2
C4—C5—H5A	120.4	C21—C20—H20A	120.2
C5—C6—C1	120.61 (15)	C20—C21—C16	119.95 (16)
C5—C6—H6A	119.7	C20—C21—H21A	120.0
C1—C6—H6A	119.7	C16—C21—H21A	120.0
O1—C7—O2	122.90 (17)	O5—C22—N4	124.8 (2)
O1—C7—C1	122.74 (16)	O5—C22—H22A	117.6
O2—C7—C1	114.34 (16)	N4—C22—H22A	117.6
N3—C8—N1	109.92 (14)	N4—C23—H23A	109.5
N3—C8—C16	124.90 (15)	N4—C23—H23B	109.5
N1—C8—C16	125.16 (14)	H23A—C23—H23B	109.5
N2—C9—N3	113.43 (14)	N4—C23—H23C	109.5
N2—C9—C10	122.24 (15)	H23A—C23—H23C	109.5
N3—C9—C10	124.33 (15)	H23B—C23—H23C	109.5
C15—C10—C11	118.88 (15)	N4—C24—H24A	109.5
C15—C10—C9	120.31 (15)	N4—C24—H24B	109.5
C11—C10—C9	120.80 (16)	H24A—C24—H24B	109.5
O3—C11—C12	117.17 (17)	N4—C24—H24C	109.5
O3—C11—C10	123.14 (15)	H24A—C24—H24C	109.5
C12—C11—C10	119.68 (17)	H24B—C24—H24C	109.5
C13—C12—C11	120.48 (18)
C8—N1—N2—C9	0.46 (17)	N3—C9—C10—C15	−4.8 (3)
C4—N1—N2—C9	178.81 (14)	N2—C9—C10—C11	−5.3 (3)
C6—C1—C2—C3	0.5 (3)	N3—C9—C10—C11	174.57 (16)
C7—C1—C2—C3	−179.4 (2)	C15—C10—C11—O3	178.67 (17)
C1—C2—C3—C4	0.4 (3)	C9—C10—C11—O3	−0.7 (3)
C2—C3—C4—C5	−0.6 (3)	C15—C10—C11—C12	0.0 (3)
C2—C3—C4—N1	179.67 (19)	C9—C10—C11—C12	−179.37 (17)
C8—N1—C4—C3	144.85 (19)	O3—C11—C12—C13	−179.39 (18)
N2—N1—C4—C3	−33.1 (2)	C10—C11—C12—C13	−0.6 (3)
C8—N1—C4—C5	−34.9 (3)	C11—C12—C13—C14	0.4 (3)
N2—N1—C4—C5	147.16 (16)	C12—C13—C14—C15	0.5 (3)
C3—C4—C5—C6	0.0 (3)	C13—C14—C15—C10	−1.1 (3)
N1—C4—C5—C6	179.74 (15)	C11—C10—C15—C14	0.9 (3)
C4—C5—C6—C1	0.8 (3)	C9—C10—C15—C14	−179.77 (16)
C2—C1—C6—C5	−1.1 (3)	N3—C8—C16—C21	106.5 (2)
C7—C1—C6—C5	178.80 (17)	N1—C8—C16—C21	−71.9 (2)
C6—C1—C7—O1	−6.0 (3)	N3—C8—C16—C17	−73.7 (2)
C2—C1—C7—O1	173.9 (2)	N1—C8—C16—C17	107.98 (19)
C6—C1—C7—O2	172.4 (2)	C21—C16—C17—O4	177.93 (15)
C2—C1—C7—O2	−7.7 (3)	C8—C16—C17—O4	−1.9 (2)
C9—N3—C8—N1	0.40 (18)	C21—C16—C17—C18	−1.7 (2)
C9—N3—C8—C16	−178.18 (15)	C8—C16—C17—C18	178.41 (15)
N2—N1—C8—N3	−0.56 (18)	O4—C17—C18—C19	−178.03 (17)
C4—N1—C8—N3	−178.70 (15)	C16—C17—C18—C19	1.6 (3)
N2—N1—C8—C16	178.01 (15)	C17—C18—C19—C20	−0.7 (3)
C4—N1—C8—C16	−0.1 (3)	C18—C19—C20—C21	−0.1 (3)
N1—N2—C9—N3	−0.22 (18)	C19—C20—C21—C16	0.0 (3)
N1—N2—C9—C10	179.69 (15)	C17—C16—C21—C20	0.9 (3)
C8—N3—C9—N2	−0.10 (19)	C8—C16—C21—C20	−179.18 (16)
C8—N3—C9—C10	179.99 (15)	C24—N4—C22—O5	3.3 (4)
N2—C9—C10—C15	175.33 (16)	C23—N4—C22—O5	179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O5i	0.90	1.68	2.583 (3)	173
O3—H1O3···N2	0.91 (3)	1.83 (3)	2.645 (2)	148 (2)
O4—H1O4···N3ii	1.00	1.79	2.7548 (19)	161
C2—H2A···O2iii	0.95	2.51	3.340 (3)	146
C12—H12A···O1iv	0.95	2.59	3.436 (2)	149
C15—H15A···O4v	0.95	2.48	3.385 (2)	160
C22—H22A···O1vi	0.95	2.42	3.085 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O5i	0.90	1.68	2.583 (3)	173
O3—H1O3⋯N2	0.91 (3)	1.83 (3)	2.645 (2)	148 (2)
O4—H1O4⋯N3ii	1.00	1.79	2.7548 (19)	161
C2—H2A⋯O2iii	0.95	2.51	3.340 (3)	146
C12—H12A⋯O1iv	0.95	2.59	3.436 (2)	149
C15—H15A⋯O4v	0.95	2.48	3.385 (2)	160
C22—H22A⋯O1vi	0.95	2.42	3.085 (3)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .