4'-(2,4-Dichloro-phen-yl)-1,1'-dimethyl-piperidine-3-spiro-3'-pyrrolidine-2'-spiro-3''-indoline-4,2''-dione.

In the title compound, C(23)H(23)Cl(2)N(3)O(2), the pyrroline ring adopts an envelope conformation and the piperidinone ring assumes a slightly twisted chair form. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate an R(2) (8) graph-set motif and a short Cl⋯Cl contact of 3.478 (1) Å occurs.

Related literature

For the effect on halogens on the conformations of organic mol­ecules, see: Awwadi et al. (2006 ▶). For the biological properties of pyrroles, see: Watson et al. (2001 ▶). For graph-set notation, see: Etter et al. (1990 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H23Cl2N3O2

M = 444.34

Triclinic,

a = 7.9398 (2) Å

b = 10.8747 (3) Å

c = 13.5367 (4) Å

α = 66.561 (2)°

β = 77.873 (1)°

γ = 83.203 (2)°

V = 1047.64 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 300 K

0.27 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.94, T max = 0.96

27365 measured reflections

6685 independent reflections

5249 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.03

6685 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000704X/ng2738sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000704X/ng2738Isup2.hkl

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

C23H23Cl2N3O2	Z = 2
Mr = 444.34	F(000) = 464
Triclinic, P1	Dx = 1.409 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9398 (2) Å	Cell parameters from 5536 reflections
b = 10.8747 (3) Å	θ = 5.7–61.9°
c = 13.5367 (4) Å	µ = 0.34 mm−1
α = 66.561 (2)°	T = 300 K
β = 77.873 (1)°	Needle, colourless
γ = 83.203 (2)°	0.27 × 0.15 × 0.12 mm
V = 1047.64 (5) Å3

Bruker Kappa APEXII CCD diffractometer	6685 independent reflections
Radiation source: fine-focus sealed tube	5249 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω and φ scan	θmax = 31.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
Tmin = 0.94, Tmax = 0.96	k = −15→15
27365 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0652P)2 + 0.3075P] where P = (Fo2 + 2Fc2)/3
6685 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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 > 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
Cl1	−0.05606 (6)	0.11850 (5)	−0.16644 (3)	0.05328 (12)
Cl2	0.52639 (5)	0.22216 (6)	−0.08290 (4)	0.05850 (14)
O1	0.59398 (16)	0.37748 (14)	0.13813 (10)	0.0564 (3)
O2	0.01383 (13)	0.08370 (10)	0.35005 (9)	0.0392 (2)
N1	0.07639 (15)	0.36986 (11)	0.21024 (10)	0.0342 (2)
N1A	0.40225 (16)	0.01730 (11)	0.32854 (10)	0.0369 (2)
N1B	0.09730 (16)	0.15644 (12)	0.46891 (9)	0.0372 (3)
H1B	0.0533	0.0947	0.5293	0.045*
C1A	0.3736 (3)	−0.12482 (15)	0.36383 (15)	0.0521 (4)
H7	0.4034	−0.1725	0.4350	0.078*
H8	0.4440	−0.1588	0.3127	0.078*
H9	0.2544	−0.1368	0.3671	0.078*
C2	0.19382 (16)	0.28182 (11)	0.28156 (10)	0.0277 (2)
C2A	0.35737 (18)	0.09368 (13)	0.22132 (11)	0.0330 (3)
H1	0.2483	0.0647	0.2182	0.040*
H2	0.4449	0.0771	0.1657	0.040*
C2B	0.09267 (16)	0.15968 (12)	0.36880 (10)	0.0312 (2)
C3	0.34300 (15)	0.24405 (12)	0.19834 (10)	0.0275 (2)
C4	0.29884 (17)	0.33178 (13)	0.08305 (10)	0.0317 (2)
H4	0.4047	0.3711	0.0334	0.038*
C4A	0.51969 (17)	0.28084 (14)	0.20663 (11)	0.0354 (3)
C4B	0.24667 (17)	0.34208 (13)	0.35377 (11)	0.0321 (2)
C5	0.1825 (2)	0.44231 (13)	0.10524 (11)	0.0383 (3)
H5A	0.2488	0.5087	0.1098	0.046*
H5B	0.1127	0.4863	0.0489	0.046*
C5A	0.5987 (2)	0.18768 (17)	0.30320 (14)	0.0442 (3)
H51	0.5450	0.2069	0.3671	0.053*
H52	0.7204	0.2048	0.2887	0.053*
C5B	0.18216 (18)	0.26551 (14)	0.46247 (11)	0.0347 (3)
C6A	0.5790 (2)	0.04095 (17)	0.32825 (14)	0.0475 (4)
H61	0.6566	0.0149	0.2736	0.057*
H62	0.6093	−0.0134	0.3992	0.057*
C6B	0.3263 (2)	0.45973 (15)	0.32860 (14)	0.0451 (3)
H6B	0.3695	0.5129	0.2563	0.054*
C7B	0.3409 (3)	0.49719 (19)	0.41348 (18)	0.0583 (5)
H7B	0.3940	0.5763	0.3976	0.070*
C8B	0.2777 (3)	0.4188 (2)	0.52044 (17)	0.0591 (5)
H8B	0.2893	0.4457	0.5758	0.071*
C9B	0.1972 (2)	0.30098 (19)	0.54744 (14)	0.0496 (4)
H9B	0.1550	0.2477	0.6198	0.060*
C11	−0.0503 (2)	0.45116 (18)	0.25448 (16)	0.0506 (4)
H11A	−0.1084	0.3957	0.3257	0.076*
H11B	−0.1328	0.4910	0.2068	0.076*
H11C	0.0066	0.5205	0.2603	0.076*
C41	0.21203 (16)	0.26281 (13)	0.03025 (10)	0.0303 (2)
C42	0.03314 (17)	0.25080 (14)	0.05212 (11)	0.0338 (3)
H42	−0.0324	0.2744	0.1079	0.041*
C43	−0.04964 (18)	0.20518 (15)	−0.00610 (12)	0.0375 (3)
H43	−0.1689	0.1990	0.0101	0.045*
C44	0.04591 (19)	0.16899 (14)	−0.08833 (11)	0.0362 (3)
C45	0.22301 (19)	0.17398 (16)	−0.11040 (12)	0.0407 (3)
H45	0.2879	0.1472	−0.1646	0.049*
C46	0.30248 (17)	0.21960 (15)	−0.05036 (11)	0.0360 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0568 (2)	0.0684 (3)	0.0460 (2)	−0.01210 (19)	−0.01697 (18)	−0.02727 (19)
Cl2	0.02974 (17)	0.0955 (4)	0.0552 (2)	−0.00686 (19)	0.00060 (15)	−0.0370 (2)
O1	0.0472 (6)	0.0649 (8)	0.0476 (6)	−0.0279 (6)	−0.0104 (5)	−0.0039 (6)
O2	0.0388 (5)	0.0369 (5)	0.0401 (5)	−0.0137 (4)	−0.0071 (4)	−0.0095 (4)
N1	0.0374 (6)	0.0304 (5)	0.0346 (5)	0.0055 (4)	−0.0123 (4)	−0.0115 (4)
N1A	0.0425 (6)	0.0310 (5)	0.0334 (6)	0.0047 (4)	−0.0116 (5)	−0.0077 (4)
N1B	0.0422 (6)	0.0363 (6)	0.0279 (5)	−0.0105 (5)	0.0006 (4)	−0.0080 (4)
C1A	0.0657 (11)	0.0321 (7)	0.0479 (9)	0.0045 (7)	−0.0105 (8)	−0.0058 (6)
C2	0.0312 (5)	0.0245 (5)	0.0260 (5)	−0.0040 (4)	−0.0068 (4)	−0.0068 (4)
C2A	0.0387 (6)	0.0298 (6)	0.0299 (6)	0.0005 (5)	−0.0078 (5)	−0.0107 (5)
C2B	0.0296 (5)	0.0298 (6)	0.0311 (6)	−0.0048 (4)	−0.0041 (4)	−0.0080 (5)
C3	0.0289 (5)	0.0270 (5)	0.0247 (5)	−0.0039 (4)	−0.0063 (4)	−0.0064 (4)
C4	0.0345 (6)	0.0319 (6)	0.0251 (5)	−0.0082 (5)	−0.0074 (4)	−0.0044 (4)
C4A	0.0309 (6)	0.0414 (7)	0.0347 (6)	−0.0059 (5)	−0.0068 (5)	−0.0137 (5)
C4B	0.0360 (6)	0.0301 (6)	0.0318 (6)	−0.0034 (5)	−0.0085 (5)	−0.0118 (5)
C5	0.0516 (8)	0.0264 (6)	0.0342 (6)	−0.0011 (5)	−0.0176 (6)	−0.0042 (5)
C5A	0.0366 (7)	0.0537 (9)	0.0452 (8)	0.0010 (6)	−0.0187 (6)	−0.0171 (7)
C5B	0.0356 (6)	0.0377 (6)	0.0318 (6)	−0.0004 (5)	−0.0058 (5)	−0.0148 (5)
C6A	0.0436 (8)	0.0490 (8)	0.0475 (8)	0.0132 (7)	−0.0194 (7)	−0.0145 (7)
C6B	0.0556 (9)	0.0349 (7)	0.0478 (8)	−0.0114 (6)	−0.0114 (7)	−0.0154 (6)
C7B	0.0708 (12)	0.0480 (9)	0.0728 (12)	−0.0092 (8)	−0.0219 (10)	−0.0343 (9)
C8B	0.0691 (12)	0.0685 (12)	0.0616 (11)	−0.0013 (9)	−0.0188 (9)	−0.0448 (10)
C9B	0.0564 (9)	0.0613 (10)	0.0385 (8)	−0.0003 (8)	−0.0084 (7)	−0.0275 (7)
C11	0.0498 (9)	0.0479 (9)	0.0586 (10)	0.0166 (7)	−0.0174 (7)	−0.0263 (8)
C41	0.0312 (6)	0.0328 (6)	0.0238 (5)	−0.0038 (4)	−0.0070 (4)	−0.0059 (4)
C42	0.0313 (6)	0.0396 (7)	0.0306 (6)	−0.0019 (5)	−0.0057 (5)	−0.0132 (5)
C43	0.0304 (6)	0.0449 (7)	0.0379 (7)	−0.0035 (5)	−0.0085 (5)	−0.0149 (6)
C44	0.0400 (7)	0.0389 (7)	0.0312 (6)	−0.0039 (5)	−0.0127 (5)	−0.0111 (5)
C45	0.0405 (7)	0.0514 (8)	0.0329 (7)	−0.0016 (6)	−0.0050 (5)	−0.0198 (6)
C46	0.0284 (6)	0.0461 (7)	0.0313 (6)	−0.0028 (5)	−0.0036 (5)	−0.0129 (5)

Cl1—C44	1.7326 (14)	C4B—C5B	1.3894 (19)
Cl2—C46	1.7402 (14)	C5—H5A	0.9700
O1—C4A	1.2057 (18)	C5—H5B	0.9700
O2—C2B	1.2226 (16)	C5A—C6A	1.514 (2)
N1—C11	1.4524 (19)	C5A—H51	0.9700
N1—C5	1.4539 (19)	C5A—H52	0.9700
N1—C2	1.4661 (16)	C5B—C9B	1.381 (2)
N1A—C2A	1.4531 (17)	C6A—H61	0.9700
N1A—C6A	1.455 (2)	C6A—H62	0.9700
N1A—C1A	1.456 (2)	C6B—C7B	1.392 (2)
N1B—C2B	1.3498 (17)	C6B—H6B	0.9300
N1B—C5B	1.3966 (18)	C7B—C8B	1.374 (3)
N1B—H1B	0.8600	C7B—H7B	0.9300
C1A—H7	0.9600	C8B—C9B	1.381 (3)
C1A—H8	0.9600	C8B—H8B	0.9300
C1A—H9	0.9600	C9B—H9B	0.9300
C2—C4B	1.5192 (17)	C11—H11A	0.9600
C2—C2B	1.5524 (16)	C11—H11B	0.9600
C2—C3	1.5916 (17)	C11—H11C	0.9600
C2A—C3	1.5329 (17)	C41—C46	1.3879 (19)
C2A—H1	0.9700	C41—C42	1.3995 (17)
C2A—H2	0.9700	C42—C43	1.3801 (19)
C3—C4A	1.5413 (17)	C42—H42	0.9300
C3—C4	1.5604 (17)	C43—C44	1.376 (2)
C4—C5	1.515 (2)	C43—H43	0.9300
C4—C41	1.5180 (17)	C44—C45	1.378 (2)
C4—H4	0.9800	C45—C46	1.384 (2)
C4A—C5A	1.507 (2)	C45—H45	0.9300
C4B—C6B	1.3811 (19)
C11—N1—C5	115.62 (12)	H5A—C5—H5B	109.2
C11—N1—C2	117.09 (12)	C4A—C5A—C6A	113.15 (13)
C5—N1—C2	106.73 (11)	C4A—C5A—H51	108.9
C2A—N1A—C6A	110.22 (12)	C6A—C5A—H51	108.9
C2A—N1A—C1A	111.33 (12)	C4A—C5A—H52	108.9
C6A—N1A—C1A	111.91 (13)	C6A—C5A—H52	108.9
C2B—N1B—C5B	111.76 (11)	H51—C5A—H52	107.8
C2B—N1B—H1B	124.1	C9B—C5B—C4B	122.56 (14)
C5B—N1B—H1B	124.2	C9B—C5B—N1B	127.53 (14)
N1A—C1A—H7	109.5	C4B—C5B—N1B	109.84 (12)
N1A—C1A—H8	109.5	N1A—C6A—C5A	110.31 (12)
H7—C1A—H8	109.5	N1A—C6A—H61	109.6
N1A—C1A—H9	109.5	C5A—C6A—H61	109.6
H7—C1A—H9	109.5	N1A—C6A—H62	109.6
H8—C1A—H9	109.5	C5A—C6A—H62	109.6
N1—C2—C4B	113.50 (10)	H61—C6A—H62	108.1
N1—C2—C2B	108.33 (10)	C4B—C6B—C7B	118.74 (16)
C4B—C2—C2B	101.02 (10)	C4B—C6B—H6B	120.6
N1—C2—C3	102.91 (9)	C7B—C6B—H6B	120.6
C4B—C2—C3	117.36 (10)	C8B—C7B—C6B	120.87 (16)
C2B—C2—C3	113.80 (10)	C8B—C7B—H7B	119.6
N1A—C2A—C3	110.54 (10)	C6B—C7B—H7B	119.6
N1A—C2A—H1	109.5	C7B—C8B—C9B	121.36 (15)
C3—C2A—H1	109.5	C7B—C8B—H8B	119.3
N1A—C2A—H2	109.5	C9B—C8B—H8B	119.3
C3—C2A—H2	109.5	C8B—C9B—C5B	117.24 (16)
H1—C2A—H2	108.1	C8B—C9B—H9B	121.4
O2—C2B—N1B	125.61 (12)	C5B—C9B—H9B	121.4
O2—C2B—C2	125.83 (12)	N1—C11—H11A	109.5
N1B—C2B—C2	108.44 (10)	N1—C11—H11B	109.5
C2A—C3—C4A	106.08 (10)	H11A—C11—H11B	109.5
C2A—C3—C4	112.94 (10)	N1—C11—H11C	109.5
C4A—C3—C4	109.87 (10)	H11A—C11—H11C	109.5
C2A—C3—C2	113.02 (10)	H11B—C11—H11C	109.5
C4A—C3—C2	110.45 (10)	C46—C41—C42	115.70 (12)
C4—C3—C2	104.55 (10)	C46—C41—C4	122.16 (12)
C5—C4—C41	111.19 (11)	C42—C41—C4	121.86 (12)
C5—C4—C3	102.12 (10)	C43—C42—C41	122.42 (13)
C41—C4—C3	116.79 (10)	C43—C42—H42	118.8
C5—C4—H4	108.8	C41—C42—H42	118.8
C41—C4—H4	108.8	C44—C43—C42	119.36 (13)
C3—C4—H4	108.8	C44—C43—H43	120.3
O1—C4A—C5A	121.14 (13)	C42—C43—H43	120.3
O1—C4A—C3	122.06 (13)	C43—C44—C45	120.56 (13)
C5A—C4A—C3	116.78 (11)	C43—C44—Cl1	120.14 (11)
C6B—C4B—C5B	119.22 (13)	C45—C44—Cl1	119.29 (11)
C6B—C4B—C2	131.56 (13)	C44—C45—C46	118.75 (13)
C5B—C4B—C2	108.82 (11)	C44—C45—H45	120.6
N1—C5—C4	102.60 (10)	C46—C45—H45	120.6
N1—C5—H5A	111.2	C45—C46—C41	123.11 (12)
C4—C5—H5A	111.2	C45—C46—Cl2	115.88 (11)
N1—C5—H5B	111.2	C41—C46—Cl2	121.01 (11)
C4—C5—H5B	111.2
C11—N1—C2—C4B	−36.10 (17)	N1—C2—C4B—C5B	115.04 (12)
C5—N1—C2—C4B	95.27 (12)	C2B—C2—C4B—C5B	−0.69 (14)
C11—N1—C2—C2B	75.23 (15)	C3—C2—C4B—C5B	−125.00 (12)
C5—N1—C2—C2B	−153.40 (11)	C11—N1—C5—C4	179.57 (12)
C11—N1—C2—C3	−163.97 (12)	C2—N1—C5—C4	47.39 (13)
C5—N1—C2—C3	−32.60 (12)	C41—C4—C5—N1	84.59 (12)
C6A—N1A—C2A—C3	−69.88 (14)	C3—C4—C5—N1	−40.70 (12)
C1A—N1A—C2A—C3	165.32 (13)	O1—C4A—C5A—C6A	−136.43 (17)
C5B—N1B—C2B—O2	−173.19 (13)	C3—C4A—C5A—C6A	41.83 (19)
C5B—N1B—C2B—C2	3.01 (16)	C6B—C4B—C5B—C9B	−1.3 (2)
N1—C2—C2B—O2	55.31 (17)	C2—C4B—C5B—C9B	−174.82 (14)
C4B—C2—C2B—O2	174.82 (13)	C6B—C4B—C5B—N1B	176.05 (14)
C3—C2—C2B—O2	−58.48 (17)	C2—C4B—C5B—N1B	2.48 (16)
N1—C2—C2B—N1B	−120.88 (12)	C2B—N1B—C5B—C9B	173.59 (15)
C4B—C2—C2B—N1B	−1.37 (13)	C2B—N1B—C5B—C4B	−3.54 (17)
C3—C2—C2B—N1B	125.33 (11)	C2A—N1A—C6A—C5A	61.70 (16)
N1A—C2A—C3—C4A	58.36 (13)	C1A—N1A—C6A—C5A	−173.83 (14)
N1A—C2A—C3—C4	178.76 (10)	C4A—C5A—C6A—N1A	−47.18 (19)
N1A—C2A—C3—C2	−62.80 (13)	C5B—C4B—C6B—C7B	0.6 (2)
N1—C2—C3—C2A	−117.16 (11)	C2—C4B—C6B—C7B	172.46 (16)
C4B—C2—C3—C2A	117.44 (11)	C4B—C6B—C7B—C8B	0.1 (3)
C2B—C2—C3—C2A	−0.17 (14)	C6B—C7B—C8B—C9B	−0.3 (3)
N1—C2—C3—C4A	124.19 (11)	C7B—C8B—C9B—C5B	−0.3 (3)
C4B—C2—C3—C4A	−1.21 (14)	C4B—C5B—C9B—C8B	1.1 (3)
C2B—C2—C3—C4A	−118.83 (11)	N1B—C5B—C9B—C8B	−175.70 (16)
N1—C2—C3—C4	6.05 (11)	C5—C4—C41—C46	142.59 (13)
C4B—C2—C3—C4	−119.35 (11)	C3—C4—C41—C46	−100.79 (14)
C2B—C2—C3—C4	123.03 (10)	C5—C4—C41—C42	−30.98 (16)
C2A—C3—C4—C5	144.01 (11)	C3—C4—C41—C42	85.64 (15)
C4A—C3—C4—C5	−97.78 (12)	C46—C41—C42—C43	−3.1 (2)
C2—C3—C4—C5	20.75 (12)	C4—C41—C42—C43	170.90 (13)
C2A—C3—C4—C41	22.49 (15)	C41—C42—C43—C44	0.5 (2)
C4A—C3—C4—C41	140.71 (12)	C42—C43—C44—C45	2.0 (2)
C2—C3—C4—C41	−100.77 (12)	C42—C43—C44—Cl1	−177.15 (11)
C2A—C3—C4A—O1	132.58 (15)	C43—C44—C45—C46	−1.8 (2)
C4—C3—C4A—O1	10.21 (19)	Cl1—C44—C45—C46	177.43 (11)
C2—C3—C4A—O1	−104.62 (16)	C44—C45—C46—C41	−1.1 (2)
C2A—C3—C4A—C5A	−45.66 (16)	C44—C45—C46—Cl2	179.75 (12)
C4—C3—C4A—C5A	−168.03 (12)	C42—C41—C46—C45	3.4 (2)
C2—C3—C4A—C5A	77.15 (15)	C4—C41—C46—C45	−170.57 (13)
N1—C2—C4B—C6B	−57.5 (2)	C42—C41—C46—Cl2	−177.48 (10)
C2B—C2—C4B—C6B	−173.18 (16)	C4—C41—C46—Cl2	8.58 (18)
C3—C2—C4B—C6B	62.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···O2i	0.86	2.02	2.8547 (15)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1B⋯O2i	0.86	2.02	2.8547 (15)	164

Symmetry code: (i) .