2-(1H-Benzotriazol-1-yl)-1-(2,5-dichloro­phen­yl)-2-(1H-1,2,4-triazol-1-yl)ethanone

Wan, J.; Zhang, S.-S.; Li, X.-M.; Li, C.-L.; Ouyang, P.-K.

doi:10.1107/S160053680504239X

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2-(1H-Benzotriazol-1-yl)-1-(2,5-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

J. Wan, S.-S. Zhang, X.-M. Li, C.-L. Li and P.-K. Ouyang

In the title compound, C₁₆H₁₀Cl₂N₆O, molecules are linked into a dimer by a pair of C—H

N hydrogen bonds. The packing is further stabilized by a π–π interaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680504239X/is6173sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680504239X/is6173Isup2.hkl Contains datablock I

CCDC reference: 296592

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.060
wR factor = 0.124
Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C16 H10 Cl2 N6 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

We have recently reported the structure of 2-(1H-benzotriazol-1-yl)-1-(2,4-dichlorophenyl)-2- (1H-1,2,4-triazol-1-yl)ethanone, (II) (Wan et al., 2005). In order to investigate the effect of the substituted Cl atoms on the conformation and biological activities, the title compound, (I), was synthesized.

All bond lengths in (I) are in good agreement with those in (II). The benzotriazole group is planar; the dihedral angle between the C9–C14 benzene ring and the N1–N3/C14/C9 triazole ring is 1.2 (2)° in (I), comparable to 1.9 (1)° in (II). The mean plane of the benzotriazole group is nearly parallel to the C1–C6 benzene ring, with a dihedral angle of 3.2 (1)°, in contrast to 33.9 (1)° in (II). The other triazole ring (N4/N5/C15/N6/C16) makes dihedral angles of 63.2 (2) and 60.4 (2)° with the C1–C6 ring and the benzotriazole group, respectively.

In the crystal structure, molecules are linked into a dimer by a weak C—H···N hydrogen bond (Fig. 2 and Table 2). The packing is further stabilized by a π–π interaction between the N1–N3/C14/C9 ring (centroid Cg1) and the C1–C6 ring (centroid Cg2), the distance between the centroids [Cg1···Cg2(x, −1 + y, z)] being 3.742 (2) Å.

Experimental top

Bromine (3.2 g, 0.02 mol, 50 ml) was added dropwise to a solution of 1-(2,5-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (5.1 g, 0.02 mol) and sodium acetate (1.6 g, 0.02 mol) in acetic acid (50 ml). The reaction was maintained for 5 h. Water (50 ml) and chloroform (20 ml) were then added. The organic layer was washed successively with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and filtered. The chloroform solution was cooled with ice–water, and then an acetone solution (10 ml) of benzotriazole (2.4 g, 0.02 mol) and triethylamine (2.8 ml) were added. The mixture was stirred at room temperature for about 3 h. The solution was then filtered, concentrated and purified by flash column chromatography (sillica gel, petroleum ether–ethyl acetate, 2:1 v/v) to afford the title compound. Single crystals were obtained by slow evaporation of an ethyl acetate–cyclohexane (3:1 v/v) solution at room temperature over a period of 6 d.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view down the c axis. Hydrogen bonds are indicated by dashed lines.

2-(1H-Benzotriazol-1-yl)-1-(2,5-dichlorophenyl)-2-(1H-1,2,4-triazol-1- yl)ethanone top

Crystal data top

C₁₆H₁₀Cl₂N₆O	F(000) = 760
M_r = 373.20	D_x = 1.546 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.6217 (6) Å	Cell parameters from 984 reflections
b = 8.6107 (8) Å	θ = 2.5–19.6°
c = 25.5989 (19) Å	µ = 0.42 mm⁻¹
β = 107.322 (2)°	T = 293 K
V = 1603.8 (2) Å³	Needle, colourless
Z = 4	0.34 × 0.07 × 0.06 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	2004 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.5°, θ_min = 2.5°
ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
T_min = 0.870, T_max = 0.975	l = −22→30
8418 measured reflections

Refinement top

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0469P)² + 0.0033P] where P = (F_o² + 2F_c²)/3
2983 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₆H₁₀Cl₂N₆O	V = 1603.8 (2) Å³
M_r = 373.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.6217 (6) Å	µ = 0.42 mm⁻¹
b = 8.6107 (8) Å	T = 293 K
c = 25.5989 (19) Å	0.34 × 0.07 × 0.06 mm
β = 107.322 (2)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2983 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2004 reflections with I > 2σ(I)
T_min = 0.870, T_max = 0.975	R_int = 0.047
8418 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.07	Δρ_max = 0.28 e Å⁻³
2983 reflections	Δρ_min = −0.20 e Å⁻³
226 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl2	−0.60724 (14)	0.88170 (12)	−0.22561 (3)	0.0668 (3)
Cl1	−0.19589 (14)	1.15467 (12)	0.00260 (4)	0.0762 (4)
O1	−0.7769 (3)	0.7264 (2)	−0.14339 (9)	0.0463 (6)
N1	−0.6242 (3)	0.4554 (3)	−0.09358 (9)	0.0306 (6)
N2	−0.6428 (3)	0.3743 (3)	−0.04957 (10)	0.0387 (6)
N3	−0.7398 (4)	0.2522 (3)	−0.06666 (11)	0.0448 (7)
N4	−0.3217 (3)	0.5697 (3)	−0.14221 (10)	0.0400 (7)
N5	−0.3388 (3)	0.5759 (3)	−0.09092 (9)	0.0299 (6)
N6	−0.0461 (3)	0.5483 (4)	−0.07861 (11)	0.0528 (8)
C1	−0.4077 (4)	0.9394 (3)	−0.06369 (13)	0.0400 (8)
H1A	−0.4105	0.8891	−0.0318	0.048*
C2	−0.3077 (4)	1.0745 (4)	−0.06049 (14)	0.0486 (9)
C3	−0.2990 (5)	1.1476 (4)	−0.10764 (18)	0.0611 (11)
H3B	−0.2300	1.2377	−0.1054	0.073*
C4	−0.3921 (5)	1.0871 (4)	−0.15753 (16)	0.0585 (10)
H4B	−0.3853	1.1362	−0.1892	0.070*
C5	−0.4955 (4)	0.9545 (4)	−0.16150 (13)	0.0432 (8)
C6	−0.5045 (4)	0.8780 (3)	−0.11447 (12)	0.0325 (7)
C7	−0.6178 (4)	0.7350 (3)	−0.11732 (11)	0.0319 (7)
C8	−0.5182 (3)	0.5968 (3)	−0.08312 (11)	0.0299 (7)
H8A	−0.4980	0.6234	−0.0445	0.036*
C9	−0.7135 (4)	0.3792 (3)	−0.14070 (11)	0.0302 (7)
C10	−0.7346 (4)	0.4057 (4)	−0.19583 (12)	0.0428 (8)
H10A	−0.6810	0.4905	−0.2076	0.051*
C11	−0.8383 (5)	0.3002 (4)	−0.23168 (14)	0.0538 (10)
H11A	−0.8563	0.3139	−0.2689	0.065*
C12	−0.9181 (5)	0.1726 (4)	−0.21422 (16)	0.0589 (10)
H12A	−0.9901	0.1051	−0.2403	0.071*
C13	−0.8941 (4)	0.1433 (4)	−0.16027 (16)	0.0519 (9)
H13A	−0.9455	0.0564	−0.1490	0.062*
C14	−0.7887 (4)	0.2499 (4)	−0.12266 (13)	0.0365 (7)
C15	−0.1436 (4)	0.5539 (4)	−0.13189 (13)	0.0441 (8)
H15A	−0.0881	0.5470	−0.1596	0.053*
C16	−0.1739 (4)	0.5633 (4)	−0.05426 (13)	0.0440 (8)
H16A	−0.1523	0.5650	−0.0165	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.0925 (7)	0.0709 (7)	0.0389 (5)	0.0121 (6)	0.0224 (5)	0.0051 (5)
Cl1	0.0698 (7)	0.0610 (7)	0.0887 (8)	−0.0232 (5)	0.0098 (6)	−0.0261 (6)
O1	0.0306 (12)	0.0428 (14)	0.0588 (15)	0.0027 (11)	0.0032 (11)	0.0040 (11)
N1	0.0320 (13)	0.0293 (15)	0.0297 (14)	−0.0042 (11)	0.0079 (11)	0.0019 (11)
N2	0.0435 (16)	0.0389 (17)	0.0353 (15)	−0.0027 (13)	0.0143 (12)	0.0039 (12)
N3	0.0491 (17)	0.0349 (17)	0.0525 (19)	−0.0077 (14)	0.0181 (14)	0.0028 (13)
N4	0.0375 (15)	0.0504 (18)	0.0326 (15)	0.0014 (13)	0.0115 (12)	0.0004 (12)
N5	0.0262 (13)	0.0343 (15)	0.0280 (13)	−0.0004 (11)	0.0061 (11)	0.0007 (11)
N6	0.0292 (15)	0.077 (2)	0.0497 (19)	0.0038 (15)	0.0081 (14)	−0.0013 (16)
C1	0.0422 (18)	0.0304 (19)	0.048 (2)	−0.0003 (15)	0.0145 (16)	0.0037 (15)
C2	0.044 (2)	0.035 (2)	0.067 (2)	−0.0042 (17)	0.0161 (18)	−0.0083 (18)
C3	0.063 (3)	0.033 (2)	0.098 (3)	−0.0097 (19)	0.040 (2)	0.002 (2)
C4	0.074 (3)	0.045 (2)	0.070 (3)	0.004 (2)	0.041 (2)	0.015 (2)
C5	0.048 (2)	0.039 (2)	0.046 (2)	0.0104 (17)	0.0185 (16)	0.0072 (16)
C6	0.0338 (17)	0.0280 (17)	0.0376 (18)	0.0035 (13)	0.0135 (14)	0.0044 (14)
C7	0.0316 (17)	0.0344 (19)	0.0310 (16)	0.0024 (14)	0.0111 (14)	−0.0009 (14)
C8	0.0291 (16)	0.0329 (18)	0.0270 (16)	−0.0055 (14)	0.0070 (13)	−0.0026 (13)
C9	0.0233 (15)	0.0327 (18)	0.0317 (17)	0.0029 (13)	0.0037 (13)	−0.0041 (13)
C10	0.0452 (19)	0.041 (2)	0.0371 (19)	0.0019 (16)	0.0037 (15)	−0.0004 (15)
C11	0.060 (2)	0.051 (2)	0.043 (2)	0.004 (2)	0.0037 (18)	−0.0132 (18)
C12	0.049 (2)	0.050 (3)	0.063 (3)	−0.0095 (19)	−0.0048 (19)	−0.023 (2)
C13	0.042 (2)	0.035 (2)	0.079 (3)	−0.0061 (17)	0.0181 (19)	−0.0067 (19)
C14	0.0310 (17)	0.0289 (18)	0.049 (2)	0.0008 (14)	0.0106 (15)	−0.0047 (15)
C15	0.0368 (19)	0.052 (2)	0.046 (2)	0.0041 (16)	0.0171 (17)	0.0016 (17)
C16	0.0345 (18)	0.058 (2)	0.0344 (18)	0.0028 (17)	0.0022 (15)	0.0011 (16)

Geometric parameters (Å, º) top

Cl1—C2	1.730 (3)	C3—H3B	0.9300
Cl2—C5	1.726 (3)	C4—C5	1.374 (4)
O1—C7	1.200 (3)	C4—H4B	0.9300
N1—C9	1.364 (3)	C5—C6	1.392 (4)
N1—N2	1.368 (3)	C6—C7	1.493 (4)
N1—C8	1.442 (3)	C7—C8	1.537 (4)
N2—N3	1.284 (3)	C8—H8A	0.9800
N3—C14	1.370 (4)	C9—C10	1.391 (4)
N4—C15	1.310 (3)	C9—C14	1.393 (4)
N4—N5	1.359 (3)	C10—C11	1.364 (4)
N5—C16	1.330 (3)	C10—H10A	0.9300
N5—C8	1.451 (3)	C11—C12	1.392 (5)
N6—C16	1.309 (4)	C11—H11A	0.9300
N6—C15	1.346 (4)	C12—C13	1.362 (5)
C1—C2	1.379 (4)	C12—H12A	0.9300
C1—C6	1.394 (4)	C13—C14	1.398 (4)
C1—H1A	0.9300	C13—H13A	0.9300
C2—C3	1.380 (5)	C15—H15A	0.9300
C3—C4	1.366 (5)	C16—H16A	0.9300

C9—N1—N2	109.6 (2)	N1—C8—N5	111.6 (2)
C9—N1—C8	132.5 (2)	N1—C8—C7	113.2 (2)
N2—N1—C8	117.9 (2)	N5—C8—C7	110.1 (2)
N3—N2—N1	109.1 (2)	N1—C8—H8A	107.2
N2—N3—C14	108.6 (2)	N5—C8—H8A	107.2
C15—N4—N5	101.6 (2)	C7—C8—H8A	107.2
C16—N5—N4	109.6 (2)	N1—C9—C10	134.1 (3)
C16—N5—C8	130.1 (2)	N1—C9—C14	103.8 (2)
N4—N5—C8	120.3 (2)	C10—C9—C14	122.2 (3)
C16—N6—C15	102.4 (2)	C11—C10—C9	116.3 (3)
C2—C1—C6	120.3 (3)	C11—C10—H10A	121.9
C2—C1—H1A	119.8	C9—C10—H10A	121.9
C6—C1—H1A	119.8	C10—C11—C12	122.1 (3)
C1—C2—C3	120.1 (3)	C10—C11—H11A	119.0
C1—C2—Cl1	120.1 (3)	C12—C11—H11A	119.0
C3—C2—Cl1	119.7 (3)	C13—C12—C11	122.2 (3)
C4—C3—C2	119.8 (3)	C13—C12—H12A	118.9
C4—C3—H3B	120.1	C11—C12—H12A	118.9
C2—C3—H3B	120.1	C12—C13—C14	116.9 (3)
C3—C4—C5	120.9 (3)	C12—C13—H13A	121.5
C3—C4—H4B	119.6	C14—C13—H13A	121.5
C5—C4—H4B	119.6	N3—C14—C9	108.9 (3)
C4—C5—C6	120.3 (3)	N3—C14—C13	130.7 (3)
C4—C5—Cl2	118.8 (3)	C9—C14—C13	120.4 (3)
C6—C5—Cl2	120.9 (3)	N4—C15—N6	115.7 (3)
C5—C6—C1	118.6 (3)	N4—C15—H15A	122.1
C5—C6—C7	121.7 (3)	N6—C15—H15A	122.1
C1—C6—C7	119.8 (3)	N6—C16—N5	110.7 (3)
O1—C7—C6	123.5 (3)	N6—C16—H16A	124.7
O1—C7—C8	121.0 (3)	N5—C16—H16A	124.7
C6—C7—C8	115.5 (2)

C9—N1—N2—N3	−0.4 (3)	C16—N5—C8—C7	128.4 (3)
C8—N1—N2—N3	−179.6 (2)	N4—N5—C8—C7	−50.1 (3)
N1—N2—N3—C14	−0.3 (3)	O1—C7—C8—N1	10.1 (4)
C15—N4—N5—C16	−0.1 (3)	C6—C7—C8—N1	−171.2 (2)
C15—N4—N5—C8	178.7 (3)	O1—C7—C8—N5	135.8 (3)
C6—C1—C2—C3	−1.7 (5)	C6—C7—C8—N5	−45.6 (3)
C6—C1—C2—Cl1	177.2 (2)	N2—N1—C9—C10	−177.8 (3)
C1—C2—C3—C4	1.0 (5)	C8—N1—C9—C10	1.3 (5)
Cl1—C2—C3—C4	−177.9 (3)	N2—N1—C9—C14	0.9 (3)
C2—C3—C4—C5	0.4 (6)	C8—N1—C9—C14	179.9 (3)
C3—C4—C5—C6	−1.1 (5)	N1—C9—C10—C11	−179.6 (3)
C3—C4—C5—Cl2	−179.0 (3)	C14—C9—C10—C11	2.0 (4)
C4—C5—C6—C1	0.5 (4)	C9—C10—C11—C12	−0.3 (5)
Cl2—C5—C6—C1	178.3 (2)	C10—C11—C12—C13	−1.5 (6)
C4—C5—C6—C7	179.1 (3)	C11—C12—C13—C14	1.6 (5)
Cl2—C5—C6—C7	−3.1 (4)	N2—N3—C14—C9	0.8 (3)
C2—C1—C6—C5	0.9 (4)	N2—N3—C14—C13	−179.4 (3)
C2—C1—C6—C7	−177.7 (3)	N1—C9—C14—N3	−1.0 (3)
C5—C6—C7—O1	−51.7 (4)	C10—C9—C14—N3	177.8 (3)
C1—C6—C7—O1	126.9 (3)	N1—C9—C14—C13	179.2 (3)
C5—C6—C7—C8	129.7 (3)	C10—C9—C14—C13	−2.0 (4)
C1—C6—C7—C8	−51.7 (4)	C12—C13—C14—N3	−179.6 (3)
C9—N1—C8—N5	−74.2 (4)	C12—C13—C14—C9	0.1 (5)
N2—N1—C8—N5	104.9 (3)	N5—N4—C15—N6	0.5 (4)
C9—N1—C8—C7	50.7 (4)	C16—N6—C15—N4	−0.6 (4)
N2—N1—C8—C7	−130.3 (2)	C15—N6—C16—N5	0.5 (4)
C16—N5—C8—N1	−105.0 (3)	N4—N5—C16—N6	−0.3 (4)
N4—N5—C8—N1	76.5 (3)	C8—N5—C16—N6	−178.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N2ⁱ	0.98	2.33	3.259 (4)	158

Symmetry code: (i) −x−1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₀Cl₂N₆O
M_r	373.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.6217 (6), 8.6107 (8), 25.5989 (19)
β (°)	107.322 (2)
V (Å³)	1603.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.34 × 0.07 × 0.06

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.870, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	8418, 2983, 2004
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.124, 1.07
No. of reflections	2983
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.20

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Cl1—C2	1.730 (3)	N1—C8	1.442 (3)
Cl2—C5	1.726 (3)	N5—C8	1.451 (3)
O1—C7	1.200 (3)	C7—C8	1.537 (4)

N1—C8—N5	111.6 (2)	N5—C8—C7	110.1 (2)
N1—C8—C7	113.2 (2)

O1—C7—C8—N1	10.1 (4)	O1—C7—C8—N5	135.8 (3)
C6—C7—C8—N1	−171.2 (2)	C6—C7—C8—N5	−45.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N2ⁱ	0.98	2.33	3.259 (4)	158

Symmetry code: (i) −x−1, −y+1, −z.

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