1,3-Dimesitylimidazolidinium tetra-chloridogold(III) dichloro-methane solvate.

The title ionic compound, (C(21)H(27)N(2))[AuCl(4)]·CH(2)Cl(2), was obtained from the reaction of 1,3-dimesitylimidazolidinium chloride with t-BuOK and a solution of AuCl(3) in tetra-hydro-furan. In the crystal structure, numerous weak C-H⋯Cl hydrogen bonds form double layers parallel to (100), which are further stabilized by π-π inter-actions between mesitylene rings [centroid-centroid distance = 4.308 (4) Å], resulting in the formation of a three-dimensional supra-molecular assembly.

Related literature

For related literature, see: Arduengo et al. (1995 ▶); da Costa et al. (2007 ▶); Adé et al. (2004 ▶); Asaji et al. (2004 ▶); Makotchenko et al. (2006 ▶); Brammer et al. (2001 ▶).

Experimental

Crystal data

(C21H27N2)[AuCl4]·CH2Cl2

M = 731.14

Monoclinic,

a = 19.590 (3) Å

b = 8.9986 (13) Å

c = 15.306 (2) Å

β = 96.601 (2)°

V = 2680.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 6.10 mm−1

T = 100 (2) K

0.30 × 0.25 × 0.10 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.146, T max = 0.546

15546 measured reflections

6083 independent reflections

4516 reflections with I > 2σ(I)

R int = 0.094

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.086

S = 0.91

6083 reflections

286 parameters

H-atom parameters constrained

Δρmax = 2.12 e Å−3

Δρmin = −2.24 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: X-SEED.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031115/hk2528sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031115/hk2528Isup2.hkl

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

(C21H27N2)[AuCl4]·CH2Cl2	F(000) = 1424
Mr = 731.14	Dx = 1.812 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3906 reflections
a = 19.590 (3) Å	θ = 2.5–27.6°
b = 8.9986 (13) Å	µ = 6.10 mm−1
c = 15.306 (2) Å	T = 100 K
β = 96.601 (2)°	Plate, orange
V = 2680.4 (7) Å3	0.30 × 0.25 × 0.10 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	6083 independent reflections
Radiation source: fine-focus sealed tube	4516 reflections with I > 2σ(I)
graphite	Rint = 0.094
ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −21→25
Tmin = 0.146, Tmax = 0.546	k = −9→11
15546 measured reflections	l = −19→19

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.0211P)2] where P = (Fo2 + 2Fc2)/3
6083 reflections	(Δ/σ)max = 0.002
286 parameters	Δρmax = 2.12 e Å−3
0 restraints	Δρmin = −2.24 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
Au1	0.816928 (12)	0.61599 (3)	0.706473 (15)	0.01554 (8)
Cl1	0.90506 (8)	0.57587 (17)	0.62476 (10)	0.0221 (4)
Cl2	0.86227 (8)	0.84160 (17)	0.74770 (10)	0.0229 (4)
Cl3	0.72796 (8)	0.65262 (18)	0.78862 (11)	0.0240 (4)
Cl4	0.76938 (8)	0.39359 (17)	0.65952 (10)	0.0220 (3)
C5	0.8618 (3)	0.1217 (7)	0.3991 (4)	0.0168 (13)
C6	0.9177 (3)	0.1185 (7)	0.3509 (4)	0.0184 (13)
C7	0.9615 (3)	−0.0040 (7)	0.3640 (4)	0.0179 (14)
H7	0.9997	−0.0101	0.3311	0.022*
C8	0.9517 (3)	−0.1156 (7)	0.4218 (4)	0.0223 (14)
C9	0.8956 (3)	−0.1060 (7)	0.4701 (4)	0.0234 (15)
H9	0.8881	−0.1829	0.5106	0.028*
C10	0.8503 (3)	0.0132 (7)	0.4605 (4)	0.0222 (15)
C11	0.7906 (3)	0.0228 (8)	0.5168 (4)	0.0259 (16)
H11C	0.7899	0.1217	0.5434	0.039*
H11A	0.7965	−0.0526	0.5632	0.039*
H11B	0.7471	0.0055	0.4796	0.039*
C12	0.9314 (3)	0.2390 (7)	0.2867 (4)	0.0228 (15)
H12C	0.8938	0.2418	0.2386	0.034*
H12A	0.9747	0.2184	0.2628	0.034*
H12B	0.9345	0.3352	0.3169	0.034*
C13	0.9994 (4)	−0.2463 (8)	0.4345 (4)	0.0299 (17)
H13B	0.9829	−0.3258	0.3937	0.045*
H13C	1.0010	−0.2824	0.4952	0.045*
H13A	1.0456	−0.2161	0.4231	0.045*
N14	0.8162 (3)	0.2491 (6)	0.3895 (3)	0.0171 (12)
C15	0.7516 (3)	0.2431 (7)	0.3605 (4)	0.0161 (13)
H15	0.7305	0.1576	0.3327	0.019*
N16	0.7176 (3)	0.3665 (5)	0.3729 (3)	0.0168 (11)
C17	0.7660 (3)	0.4782 (7)	0.4162 (4)	0.0170 (14)
H17A	0.7505	0.5136	0.4719	0.020*
H17B	0.7707	0.5644	0.3772	0.020*
C18	0.8333 (3)	0.3929 (7)	0.4333 (4)	0.0210 (14)
H18A	0.8707	0.4441	0.4069	0.025*
H18B	0.8471	0.3795	0.4971	0.025*
C19	0.6464 (3)	0.4010 (7)	0.3447 (4)	0.0165 (13)
C20	0.5985 (3)	0.3755 (7)	0.4036 (4)	0.0207 (14)
C21	0.5323 (3)	0.4244 (7)	0.3781 (4)	0.0191 (14)
H21	0.4983	0.4097	0.4168	0.023*
C22	0.5134 (3)	0.4949 (7)	0.2971 (4)	0.0209 (15)
C23	0.5620 (3)	0.5118 (7)	0.2400 (4)	0.0210 (15)
H23	0.5492	0.5574	0.1845	0.025*
C24	0.6297 (3)	0.4639 (7)	0.2613 (4)	0.0202 (15)
C25	0.6811 (3)	0.4777 (7)	0.1960 (4)	0.0230 (15)
H25C	0.7222	0.5291	0.2236	0.034*
H25B	0.6609	0.5347	0.1449	0.034*
H25A	0.6938	0.3785	0.1771	0.034*
C26	0.6168 (4)	0.2988 (8)	0.4893 (4)	0.0303 (17)
H26C	0.5780	0.3048	0.5243	0.045*
H26B	0.6571	0.3467	0.5212	0.045*
H26A	0.6272	0.1942	0.4787	0.045*
C27	0.4414 (3)	0.5523 (9)	0.2740 (5)	0.0317 (18)
H27C	0.4317	0.5619	0.2100	0.048*
H27A	0.4369	0.6496	0.3015	0.048*
H27B	0.4087	0.4826	0.2955	0.048*
C28	0.6210 (4)	0.7360 (8)	0.9489 (4)	0.0303 (17)
H28B	0.6054	0.8168	0.9075	0.036*
H28A	0.6592	0.6833	0.9251	0.036*
Cl29	0.65120 (9)	0.8137 (2)	1.05262 (12)	0.0335 (4)
Cl30	0.55384 (12)	0.6129 (3)	0.95642 (15)	0.0580 (6)

	U11	U22	U33	U12	U13	U23
Au1	0.01694 (12)	0.01813 (12)	0.01117 (12)	−0.00007 (12)	0.00005 (8)	0.00093 (11)
Cl1	0.0243 (8)	0.0229 (8)	0.0202 (8)	−0.0012 (7)	0.0073 (7)	−0.0006 (6)
Cl2	0.0252 (9)	0.0197 (8)	0.0236 (9)	−0.0021 (7)	0.0019 (7)	−0.0038 (6)
Cl3	0.0232 (8)	0.0241 (9)	0.0263 (9)	0.0015 (7)	0.0089 (7)	0.0007 (7)
Cl4	0.0268 (8)	0.0220 (8)	0.0167 (8)	−0.0060 (7)	0.0004 (6)	−0.0012 (7)
C5	0.019 (3)	0.019 (3)	0.010 (3)	−0.002 (3)	−0.004 (2)	−0.002 (3)
C6	0.014 (3)	0.027 (4)	0.014 (3)	−0.002 (3)	−0.002 (2)	−0.008 (3)
C7	0.011 (3)	0.028 (4)	0.015 (3)	0.004 (3)	0.002 (3)	−0.009 (3)
C8	0.032 (4)	0.024 (3)	0.010 (3)	0.007 (3)	−0.003 (3)	−0.004 (3)
C9	0.029 (4)	0.024 (4)	0.017 (3)	−0.003 (3)	0.001 (3)	−0.001 (3)
C10	0.024 (4)	0.027 (4)	0.015 (4)	0.000 (3)	−0.004 (3)	0.001 (3)
C11	0.027 (4)	0.031 (4)	0.020 (4)	0.006 (3)	0.006 (3)	0.007 (3)
C12	0.015 (3)	0.027 (4)	0.027 (4)	0.001 (3)	0.005 (3)	0.002 (3)
C13	0.036 (4)	0.039 (4)	0.014 (4)	0.013 (4)	−0.003 (3)	−0.003 (3)
N14	0.014 (3)	0.025 (3)	0.012 (3)	0.001 (2)	0.000 (2)	−0.002 (2)
C15	0.021 (3)	0.019 (3)	0.008 (3)	−0.005 (3)	0.002 (3)	0.006 (2)
N16	0.017 (3)	0.015 (3)	0.018 (3)	0.000 (2)	0.002 (2)	−0.004 (2)
C17	0.015 (3)	0.017 (3)	0.017 (3)	−0.002 (3)	−0.004 (3)	−0.003 (3)
C18	0.013 (3)	0.025 (4)	0.025 (3)	−0.007 (3)	0.002 (3)	−0.006 (3)
C19	0.018 (3)	0.014 (3)	0.017 (3)	0.003 (3)	0.001 (3)	0.001 (3)
C20	0.025 (3)	0.019 (3)	0.018 (3)	−0.003 (3)	0.003 (3)	−0.004 (3)
C21	0.017 (3)	0.024 (4)	0.017 (3)	−0.006 (3)	0.004 (3)	0.000 (3)
C22	0.011 (3)	0.025 (4)	0.026 (4)	−0.002 (3)	0.000 (3)	−0.001 (3)
C23	0.022 (4)	0.023 (4)	0.018 (4)	0.008 (3)	−0.002 (3)	0.000 (3)
C24	0.021 (4)	0.020 (3)	0.019 (4)	−0.004 (3)	0.001 (3)	−0.004 (3)
C25	0.026 (4)	0.028 (4)	0.016 (4)	0.003 (3)	0.006 (3)	−0.001 (3)
C26	0.030 (4)	0.035 (4)	0.026 (4)	−0.006 (3)	0.002 (3)	0.004 (3)
C27	0.020 (4)	0.049 (5)	0.026 (4)	0.006 (4)	0.005 (3)	0.006 (4)
C28	0.039 (4)	0.032 (4)	0.020 (4)	0.004 (4)	0.005 (3)	0.004 (3)
Cl29	0.0332 (10)	0.0352 (10)	0.0312 (10)	−0.0055 (9)	0.0001 (8)	0.0011 (8)
Cl30	0.0640 (15)	0.0613 (15)	0.0492 (13)	−0.0310 (13)	0.0087 (11)	−0.0151 (12)

Au1—Cl1	2.2742 (16)	N16—C17	1.484 (7)
Au1—Cl2	2.2759 (16)	C17—C18	1.523 (8)
Au1—Cl3	2.2872 (16)	C17—H17A	0.9900
Au1—Cl4	2.2881 (16)	C17—H17B	0.9900
C5—C6	1.390 (8)	C18—H18A	0.9900
C5—C10	1.391 (8)	C18—H18B	0.9900
C5—N14	1.449 (8)	C19—C20	1.392 (9)
C6—C7	1.397 (8)	C19—C24	1.401 (8)
C6—C12	1.508 (8)	C20—C21	1.383 (9)
C7—C8	1.367 (9)	C20—C26	1.489 (9)
C7—H7	0.9500	C21—C22	1.404 (9)
C8—C9	1.397 (9)	C21—H21	0.9500
C8—C13	1.501 (9)	C22—C23	1.373 (9)
C9—C10	1.389 (9)	C22—C27	1.505 (8)
C9—H9	0.9500	C23—C24	1.397 (8)
C10—C11	1.533 (9)	C23—H23	0.9500
C11—H11C	0.9800	C24—C25	1.503 (9)
C11—H11A	0.9800	C25—H25C	0.9800
C11—H11B	0.9800	C25—H25B	0.9800
C12—H12C	0.9800	C25—H25A	0.9800
C12—H12A	0.9800	C26—H26C	0.9800
C12—H12B	0.9800	C26—H26B	0.9800
C13—H13B	0.9800	C26—H26A	0.9800
C13—H13C	0.9800	C27—H27C	0.9800
C13—H13A	0.9800	C27—H27A	0.9800
N14—C15	1.294 (7)	C27—H27B	0.9800
N14—C18	1.478 (8)	C28—Cl30	1.734 (7)
C15—N16	1.320 (8)	C28—Cl29	1.773 (7)
C15—H15	0.9500	C28—H28B	0.9900
N16—C19	1.446 (7)	C28—H28A	0.9900
Cl1—Au1—Cl2	89.85 (6)	C18—C17—H17A	111.1
Cl1—Au1—Cl3	179.15 (6)	N16—C17—H17B	111.1
Cl2—Au1—Cl3	90.96 (6)	C18—C17—H17B	111.1
Cl1—Au1—Cl4	89.76 (6)	H17A—C17—H17B	109.1
Cl2—Au1—Cl4	177.57 (6)	N14—C18—C17	102.5 (4)
Cl3—Au1—Cl4	89.44 (6)	N14—C18—H18A	111.3
C6—C5—C10	122.8 (6)	C17—C18—H18A	111.3
C6—C5—N14	118.4 (5)	N14—C18—H18B	111.3
C10—C5—N14	118.6 (6)	C17—C18—H18B	111.3
C5—C6—C7	116.7 (6)	H18A—C18—H18B	109.2
C5—C6—C12	122.7 (6)	C20—C19—C24	123.6 (6)
C7—C6—C12	120.6 (6)	C20—C19—N16	118.1 (5)
C8—C7—C6	122.9 (6)	C24—C19—N16	118.3 (5)
C8—C7—H7	118.6	C21—C20—C19	116.4 (6)
C6—C7—H7	118.6	C21—C20—C26	121.3 (6)
C7—C8—C9	118.4 (6)	C19—C20—C26	122.4 (6)
C7—C8—C13	121.9 (6)	C20—C21—C22	122.5 (6)
C9—C8—C13	119.7 (6)	C20—C21—H21	118.7
C10—C9—C8	121.5 (6)	C22—C21—H21	118.7
C10—C9—H9	119.2	C23—C22—C21	118.7 (6)
C8—C9—H9	119.2	C23—C22—C27	120.8 (6)
C9—C10—C5	117.7 (6)	C21—C22—C27	120.5 (6)
C9—C10—C11	120.2 (6)	C22—C23—C24	121.8 (6)
C5—C10—C11	122.2 (6)	C22—C23—H23	119.1
C10—C11—H11C	109.5	C24—C23—H23	119.1
C10—C11—H11A	109.5	C23—C24—C19	116.9 (6)
H11C—C11—H11A	109.5	C23—C24—C25	120.7 (6)
C10—C11—H11B	109.5	C19—C24—C25	122.4 (6)
H11C—C11—H11B	109.5	C24—C25—H25C	109.5
H11A—C11—H11B	109.5	C24—C25—H25B	109.5
C6—C12—H12C	109.5	H25C—C25—H25B	109.5
C6—C12—H12A	109.5	C24—C25—H25A	109.5
H12C—C12—H12A	109.5	H25C—C25—H25A	109.5
C6—C12—H12B	109.5	H25B—C25—H25A	109.5
H12C—C12—H12B	109.5	C20—C26—H26C	109.5
H12A—C12—H12B	109.5	C20—C26—H26B	109.5
C8—C13—H13B	109.5	H26C—C26—H26B	109.5
C8—C13—H13C	109.5	C20—C26—H26A	109.5
H13B—C13—H13C	109.5	H26C—C26—H26A	109.5
C8—C13—H13A	109.5	H26B—C26—H26A	109.5
H13B—C13—H13A	109.5	C22—C27—H27C	109.5
H13C—C13—H13A	109.5	C22—C27—H27A	109.5
C15—N14—C5	124.6 (5)	H27C—C27—H27A	109.5
C15—N14—C18	110.7 (5)	C22—C27—H27B	109.5
C5—N14—C18	122.8 (5)	H27C—C27—H27B	109.5
N14—C15—N16	113.9 (6)	H27A—C27—H27B	109.5
N14—C15—H15	123.0	Cl30—C28—Cl29	111.7 (4)
N16—C15—H15	123.0	Cl30—C28—H28B	109.3
C15—N16—C19	128.6 (5)	Cl29—C28—H28B	109.3
C15—N16—C17	109.1 (5)	Cl30—C28—H28A	109.3
C19—N16—C17	122.2 (5)	Cl29—C28—H28A	109.3
N16—C17—C18	103.4 (5)	H28B—C28—H28A	107.9
N16—C17—H17A	111.1
C10—C5—C6—C7	2.7 (9)	C19—N16—C17—C18	−180.0 (5)
N14—C5—C6—C7	178.1 (5)	C15—N14—C18—C17	−5.3 (7)
C10—C5—C6—C12	−177.8 (6)	C5—N14—C18—C17	−170.6 (5)
N14—C5—C6—C12	−2.4 (8)	N16—C17—C18—N14	5.5 (6)
C5—C6—C7—C8	−1.1 (9)	C15—N16—C19—C20	94.1 (8)
C12—C6—C7—C8	179.4 (6)	C17—N16—C19—C20	−91.1 (7)
C6—C7—C8—C9	−0.2 (9)	C15—N16—C19—C24	−88.5 (8)
C6—C7—C8—C13	179.9 (6)	C17—N16—C19—C24	86.3 (7)
C7—C8—C9—C10	−0.1 (9)	C24—C19—C20—C21	−3.9 (9)
C13—C8—C9—C10	179.9 (6)	N16—C19—C20—C21	173.3 (5)
C8—C9—C10—C5	1.6 (9)	C24—C19—C20—C26	175.6 (6)
C8—C9—C10—C11	−177.9 (6)	N16—C19—C20—C26	−7.2 (9)
C6—C5—C10—C9	−3.0 (9)	C19—C20—C21—C22	0.6 (9)
N14—C5—C10—C9	−178.4 (5)	C26—C20—C21—C22	−178.9 (6)
C6—C5—C10—C11	176.6 (6)	C20—C21—C22—C23	2.0 (10)
N14—C5—C10—C11	1.1 (9)	C20—C21—C22—C27	−177.2 (6)
C6—C5—N14—C15	118.6 (7)	C21—C22—C23—C24	−1.4 (10)
C10—C5—N14—C15	−65.8 (8)	C27—C22—C23—C24	177.8 (6)
C6—C5—N14—C18	−78.2 (7)	C22—C23—C24—C19	−1.6 (9)
C10—C5—N14—C18	97.4 (7)	C22—C23—C24—C25	177.3 (6)
C5—N14—C15—N16	167.8 (5)	C20—C19—C24—C23	4.5 (9)
C18—N14—C15—N16	2.9 (7)	N16—C19—C24—C23	−172.8 (5)
N14—C15—N16—C19	176.4 (6)	C20—C19—C24—C25	−174.5 (6)
N14—C15—N16—C17	1.0 (7)	N16—C19—C24—C25	8.3 (9)
C15—N16—C17—C18	−4.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cl1i	0.95	2.78	3.706 (6)	164
C12—H12C···Cl4ii	0.98	2.87	3.724 (6)	147
C15—H15···Cl3ii	0.95	2.87	3.740 (7)	152
C15—H15···Cl4ii	0.95	2.88	3.368 (6)	113
C17—H17A···Cl4	0.99	3.05	3.794 (6)	133
C17—H17B···Cl2iii	0.99	2.95	3.736 (6)	137
C17—H17B···Cl3iii	0.99	2.96	3.882 (6)	155
C18—H18B···Cl1	0.99	2.78	3.511 (6)	131
C25—H25A···Cl4ii	0.98	2.89	3.832 (6)	162
C25—H25B···Cl29iv	0.98	2.88	3.742 (7)	148
C25—H25C···Cl2iii	0.98	2.97	3.901 (6)	160
C25—H25C···Cl3iii	0.98	3.03	3.691 (6)	126
C26—H26B···Cl4	0.98	2.90	3.829 (7)	158
C27—H27C···Cl30v	0.98	3.04	3.838 (8)	140
C28—H28A···Cl3	0.99	2.63	3.486 (7)	145

Table 1

Hydrogen-bond geometry (Å, °) (with cut-off parameters as in Brammer et al., 2001 ▶)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cl1i	0.95	2.78	3.706 (6)	164
C12—H12C⋯Cl4ii	0.98	2.87	3.724 (6)	147
C15—H15⋯Cl3ii	0.95	2.87	3.740 (7)	152
C15—H15⋯Cl4ii	0.95	2.88	3.368 (6)	113
C17—H17A⋯Cl4	0.99	3.05	3.794 (6)	133
C17—H17B⋯Cl2iii	0.99	2.95	3.736 (6)	137
C17—H17B⋯Cl3iii	0.99	2.96	3.882 (6)	155
C18—H18B⋯Cl1	0.99	2.78	3.511 (6)	131
C25—H25A⋯Cl4ii	0.98	2.89	3.832 (6)	162
C25—H25B⋯Cl29iv	0.98	2.88	3.742 (7)	148
C25—H25C⋯Cl2iii	0.98	2.97	3.901 (6)	160
C25—H25C⋯Cl3iii	0.98	3.03	3.691 (6)	126
C26—H26B⋯Cl4	0.98	2.90	3.829 (7)	158
C27—H27C⋯Cl30v	0.98	3.04	3.838 (8)	140
C28—H28A⋯Cl3	0.99	2.63	3.486 (7)	145

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