Amiloride hydro­chloride methanol disolvate

Ton, C.Q.; Bolte, M.

doi:10.1107/S1600536810017484

organic compounds

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Volume 66| Part 6| June 2010| Page o1364

https://doi.org/10.1107/S1600536810017484

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Amiloride hydrochloride methanol disolvate

Cuong Quoc Ton ^a and Michael Bolte ^b ^*

^aInstitut für Organische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 11 May 2010; accepted 12 May 2010; online 15 May 2010)

In the crystal of the title compound [systematic name: 2-(3,5-diamino-6-chloropyrazin-2-ylcarbonyl)guanidinium chloride methanol disolvate], C₆H₉ClN₇O⁺·Cl⁻·2CH₃OH , the components are connected by N—H⋯N, N—H⋯Cl, N—H⋯O, O—H⋯Cl and O—H⋯O hydrogen bonds into a three-dimensional network. The dihedral angle between the aromatic ring and the guanidine residue is 6.0 (2)°.

Related literature

For other salts of amiloride, see: Pretscher et al. (2001 ); Zeslawska et al. (2004 ).

Experimental

Crystal data

C₆H₉ClN₇O⁺·Cl⁻·2CH₄O
M_r = 330.19
Monoclinic, P 2₁ /n
a = 5.9473 (5) Å
b = 16.7278 (17) Å
c = 14.7784 (15) Å
β = 90.080 (8)°
V = 1470.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 173 K
0.30 × 0.25 × 0.20 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ; Blessing, 1995 ) T_min = 0.874, T_max = 0.914
19184 measured reflections
2739 independent reflections
1852 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.080
S = 0.96
2739 reflections
212 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N31—H31A⋯N4ⁱ	0.88 (1)	2.14 (1)	2.996 (3)	165 (3)
N31—H31B⋯Cl1ⁱⁱ	0.87 (1)	2.50 (2)	3.281 (3)	150 (3)
N51—H51A⋯Cl1ⁱⁱⁱ	0.88 (1)	2.54 (1)	3.396 (3)	165 (3)
N51—H51B⋯O11	0.88 (1)	2.11 (2)	2.781 (3)	133 (3)
N12—H12⋯O2M^iv	0.87 (1)	2.14 (2)	2.912 (3)	149 (3)
N14—H14A⋯Cl1^v	0.88 (1)	2.34 (1)	3.188 (3)	162 (3)
N14—H14B⋯O2M^iv	0.88 (1)	1.93 (2)	2.783 (3)	162 (3)
N15—H15A⋯Cl1^v	0.88 (1)	2.61 (2)	3.367 (3)	145 (3)
N15—H15B⋯O11	0.88 (1)	2.03 (3)	2.688 (3)	131 (3)
O1M—H1M⋯Cl1	0.84	2.26	3.091 (2)	171
O2M—H2M⋯O1M	0.84	1.91	2.745 (3)	170
Symmetry codes: (i) -x+2, -y, -z+1; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x-1, y, z.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810017484/ng2772sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017484/ng2772Isup2.hkl

checkCIF report

Related literature top

For other pseudopolymorphs of amiloride, see: Pretscher et al. (2001); Zeslawska et al. (2004).

Experimental top

Crystals of the title structure were obtained by recrystallization of amiloride hydrochloride (100 mg) from a methanol (3 g) solution.

Structure description top

For other pseudopolymorphs of amiloride, see: Pretscher et al. (2001); Zeslawska et al. (2004).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Perspective view of the asymmetric unit of the title compound. Displacement ellipsoids are at the 50° probability level.

2-(3,5-diamino-6-chloropyrazin-2-ylcarbonyl)guanidinium chloride methanol disolvate top

Crystal data top

C₆H₉ClN₇O⁺·Cl⁻·2CH₄O	F(000) = 688
M_r = 330.19	D_x = 1.492 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11166 reflections
a = 5.9473 (5) Å	θ = 3.7–25.7°
b = 16.7278 (17) Å	µ = 0.46 mm⁻¹
c = 14.7784 (15) Å	T = 173 K
β = 90.080 (8)°	Block, colourless
V = 1470.2 (2) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Stoe IPDS II two-circle diffractometer	2739 independent reflections
Radiation source: fine-focus sealed tube	1852 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
ω scans	θ_max = 25.6°, θ_min = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −7→7
T_min = 0.874, T_max = 0.914	k = −20→20
19184 measured reflections	l = −17→17

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.0253P)²] where P = (F_o² + 2F_c²)/3
2739 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.22 e Å⁻³
9 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₆H₉ClN₇O⁺·Cl⁻·2CH₄O	V = 1470.2 (2) Å³
M_r = 330.19	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.9473 (5) Å	µ = 0.46 mm⁻¹
b = 16.7278 (17) Å	T = 173 K
c = 14.7784 (15) Å	0.30 × 0.25 × 0.20 mm
β = 90.080 (8)°

Data collection top

Stoe IPDS II two-circle diffractometer	2739 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	1852 reflections with I > 2σ(I)
T_min = 0.874, T_max = 0.914	R_int = 0.071
19184 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	9 restraints
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.22 e Å⁻³
2739 reflections	Δρ_min = −0.25 e Å⁻³
212 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
N1	0.4136 (4)	0.07364 (14)	0.32999 (16)	0.0187 (6)
C2	0.5851 (5)	0.02607 (17)	0.32413 (18)	0.0179 (6)
Cl2	0.62266 (14)	−0.02883 (5)	0.22493 (5)	0.0315 (2)
C3	0.7485 (5)	0.01732 (16)	0.39568 (19)	0.0182 (6)
N31	0.9232 (4)	−0.03176 (16)	0.38692 (17)	0.0241 (6)
H31A	1.006 (5)	−0.0400 (18)	0.4354 (14)	0.029*
H31B	0.939 (5)	−0.0621 (16)	0.3394 (14)	0.029*
N4	0.7256 (4)	0.06106 (13)	0.47133 (16)	0.0179 (5)
C5	0.5473 (5)	0.11111 (16)	0.47856 (19)	0.0173 (6)
N51	0.5303 (5)	0.15414 (15)	0.55477 (18)	0.0256 (6)
H51A	0.624 (4)	0.1497 (18)	0.6007 (15)	0.031*
H51B	0.410 (3)	0.1839 (16)	0.561 (2)	0.031*
C6	0.3874 (5)	0.11725 (17)	0.40695 (19)	0.0168 (6)
C11	0.1930 (5)	0.17089 (18)	0.4093 (2)	0.0202 (7)
O11	0.1433 (4)	0.21444 (12)	0.47391 (14)	0.0249 (5)
N12	0.0642 (4)	0.16832 (14)	0.33015 (15)	0.0173 (5)
H12	0.110 (5)	0.1370 (14)	0.2874 (15)	0.021*
C13	−0.1158 (5)	0.21632 (17)	0.3097 (2)	0.0196 (7)
N14	−0.2054 (4)	0.20867 (16)	0.22820 (18)	0.0250 (6)
H14A	−0.326 (3)	0.2377 (16)	0.218 (2)	0.030*
H14B	−0.134 (5)	0.1739 (15)	0.1935 (18)	0.030*
N15	−0.1985 (4)	0.26602 (16)	0.37008 (18)	0.0250 (6)
H15A	−0.310 (4)	0.2979 (16)	0.355 (2)	0.030*
H15B	−0.141 (5)	0.2664 (19)	0.4246 (11)	0.030*
Cl1	0.36907 (12)	0.32420 (4)	0.23835 (5)	0.02329 (18)
O1M	0.4195 (4)	0.44145 (13)	0.39875 (15)	0.0335 (6)
H1M	0.4001	0.4139	0.3519	0.050*
C1M	0.2507 (6)	0.4216 (2)	0.4641 (2)	0.0355 (8)
H1M1	0.2637	0.3650	0.4802	0.053*
H1M2	0.1015	0.4318	0.4384	0.053*
H1M3	0.2716	0.4545	0.5183	0.053*
O2M	0.4108 (4)	0.59993 (13)	0.35076 (15)	0.0315 (6)
H2M	0.4196	0.5504	0.3592	0.047*
C2MA	0.2302 (6)	0.6318 (2)	0.4037 (2)	0.0370 (9)
H2M1	0.0883	0.6071	0.3848	0.056*
H2M2	0.2214	0.6898	0.3945	0.056*
H2M3	0.2573	0.6205	0.4678	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0148 (14)	0.0184 (13)	0.0229 (14)	−0.0003 (11)	−0.0025 (10)	0.0018 (11)
C2	0.0171 (15)	0.0209 (15)	0.0157 (14)	−0.0018 (13)	−0.0030 (12)	0.0000 (12)
Cl2	0.0278 (5)	0.0391 (5)	0.0276 (4)	0.0122 (4)	−0.0061 (3)	−0.0114 (4)
C3	0.0142 (15)	0.0149 (15)	0.0254 (16)	−0.0011 (13)	0.0002 (12)	0.0037 (13)
N31	0.0209 (14)	0.0244 (15)	0.0268 (15)	0.0082 (12)	−0.0059 (12)	−0.0050 (12)
N4	0.0133 (13)	0.0146 (12)	0.0258 (14)	0.0018 (10)	−0.0036 (10)	0.0012 (10)
C5	0.0172 (16)	0.0129 (14)	0.0220 (16)	−0.0037 (12)	−0.0017 (12)	0.0012 (12)
N51	0.0250 (16)	0.0269 (15)	0.0250 (15)	0.0067 (12)	−0.0070 (12)	−0.0061 (12)
C6	0.0125 (15)	0.0141 (14)	0.0238 (16)	−0.0012 (12)	−0.0014 (12)	−0.0002 (12)
C11	0.0186 (16)	0.0162 (15)	0.0257 (16)	−0.0046 (13)	−0.0006 (13)	0.0037 (14)
O11	0.0265 (12)	0.0212 (11)	0.0268 (12)	0.0062 (9)	−0.0021 (9)	−0.0042 (9)
N12	0.0174 (13)	0.0166 (13)	0.0180 (13)	0.0043 (11)	−0.0024 (10)	−0.0011 (10)
C13	0.0141 (15)	0.0156 (15)	0.0290 (17)	−0.0004 (12)	0.0001 (13)	0.0027 (13)
N14	0.0197 (15)	0.0272 (15)	0.0280 (16)	0.0083 (11)	−0.0061 (12)	0.0000 (12)
N15	0.0197 (15)	0.0263 (15)	0.0290 (15)	0.0103 (12)	−0.0039 (12)	−0.0018 (12)
Cl1	0.0196 (4)	0.0206 (4)	0.0296 (4)	0.0024 (3)	−0.0022 (3)	0.0006 (3)
O1M	0.0372 (14)	0.0317 (14)	0.0317 (13)	−0.0091 (11)	0.0034 (11)	−0.0026 (10)
C1M	0.040 (2)	0.0347 (19)	0.0318 (19)	−0.0092 (17)	−0.0015 (16)	0.0054 (16)
O2M	0.0344 (14)	0.0271 (13)	0.0328 (13)	−0.0055 (11)	−0.0006 (11)	0.0064 (11)
C2MA	0.039 (2)	0.033 (2)	0.039 (2)	−0.0027 (17)	0.0032 (17)	0.0001 (16)

Geometric parameters (Å, º) top

N1—C2	1.297 (4)	N12—H12	0.866 (10)
N1—C6	1.360 (4)	C13—N15	1.316 (4)
C2—C3	1.443 (4)	C13—N14	1.322 (4)
C2—Cl2	1.745 (3)	N14—H14A	0.880 (10)
C3—N31	1.331 (4)	N14—H14B	0.884 (10)
C3—N4	1.343 (4)	N15—H15A	0.880 (10)
N31—H31A	0.880 (10)	N15—H15B	0.876 (10)
N31—H31B	0.872 (10)	O1M—C1M	1.432 (4)
N4—C5	1.355 (4)	O1M—H1M	0.8400
C5—N51	1.341 (4)	C1M—H1M1	0.9800
C5—C6	1.426 (4)	C1M—H1M2	0.9800
N51—H51A	0.879 (10)	C1M—H1M3	0.9800
N51—H51B	0.878 (10)	O2M—C2MA	1.433 (4)
C6—C11	1.464 (4)	O2M—H2M	0.8400
C11—O11	1.238 (3)	C2MA—H2M1	0.9800
C11—N12	1.398 (4)	C2MA—H2M2	0.9800
N12—C13	1.371 (4)	C2MA—H2M3	0.9800

C2—N1—C6	118.4 (2)	C11—N12—H12	117 (2)
N1—C2—C3	122.9 (3)	N15—C13—N14	121.9 (3)
N1—C2—Cl2	118.7 (2)	N15—C13—N12	120.8 (3)
C3—C2—Cl2	118.4 (2)	N14—C13—N12	117.2 (3)
N31—C3—N4	119.8 (3)	C13—N14—H14A	116 (2)
N31—C3—C2	121.1 (3)	C13—N14—H14B	114 (2)
N4—C3—C2	119.1 (3)	H14A—N14—H14B	131 (3)
C3—N31—H31A	117 (2)	C13—N15—H15A	119 (2)
C3—N31—H31B	122 (2)	C13—N15—H15B	119 (2)
H31A—N31—H31B	120 (3)	H15A—N15—H15B	122 (3)
C3—N4—C5	118.8 (2)	C1M—O1M—H1M	109.5
N51—C5—N4	117.2 (3)	O1M—C1M—H1M1	109.5
N51—C5—C6	122.3 (3)	O1M—C1M—H1M2	109.5
N4—C5—C6	120.5 (3)	H1M1—C1M—H1M2	109.5
C5—N51—H51A	124 (2)	O1M—C1M—H1M3	109.5
C5—N51—H51B	117 (2)	H1M1—C1M—H1M3	109.5
H51A—N51—H51B	119 (3)	H1M2—C1M—H1M3	109.5
N1—C6—C5	120.3 (3)	C2MA—O2M—H2M	109.5
N1—C6—C11	116.1 (2)	O2M—C2MA—H2M1	109.5
C5—C6—C11	123.6 (3)	O2M—C2MA—H2M2	109.5
O11—C11—N12	122.2 (3)	H2M1—C2MA—H2M2	109.5
O11—C11—C6	124.6 (3)	O2M—C2MA—H2M3	109.5
N12—C11—C6	113.2 (3)	H2M1—C2MA—H2M3	109.5
C13—N12—C11	126.4 (2)	H2M2—C2MA—H2M3	109.5
C13—N12—H12	116 (2)

C6—N1—C2—C3	0.1 (4)	N51—C5—C6—N1	178.7 (3)
C6—N1—C2—Cl2	−178.9 (2)	N4—C5—C6—N1	−0.8 (4)
N1—C2—C3—N31	−179.6 (3)	N51—C5—C6—C11	0.6 (4)
Cl2—C2—C3—N31	−0.5 (4)	N4—C5—C6—C11	−178.9 (3)
N1—C2—C3—N4	−1.1 (4)	N1—C6—C11—O11	179.6 (3)
Cl2—C2—C3—N4	178.0 (2)	C5—C6—C11—O11	−2.2 (4)
N31—C3—N4—C5	179.5 (3)	N1—C6—C11—N12	−0.1 (4)
C2—C3—N4—C5	1.1 (4)	C5—C6—C11—N12	178.1 (3)
C3—N4—C5—N51	−179.7 (2)	O11—C11—N12—C13	6.0 (4)
C3—N4—C5—C6	−0.2 (4)	C6—C11—N12—C13	−174.3 (3)
C2—N1—C6—C5	0.8 (4)	C11—N12—C13—N15	−6.9 (4)
C2—N1—C6—C11	179.0 (3)	C11—N12—C13—N14	175.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N31—H31A···N4ⁱ	0.88 (1)	2.14 (1)	2.996 (3)	165 (3)
N31—H31B···Cl1ⁱⁱ	0.87 (1)	2.50 (2)	3.281 (3)	150 (3)
N51—H51A···Cl1ⁱⁱⁱ	0.88 (1)	2.54 (1)	3.396 (3)	165 (3)
N51—H51B···O11	0.88 (1)	2.11 (2)	2.781 (3)	133 (3)
N12—H12···O2M^iv	0.87 (1)	2.14 (2)	2.912 (3)	149 (3)
N14—H14A···Cl1^v	0.88 (1)	2.34 (1)	3.188 (3)	162 (3)
N14—H14B···O2M^iv	0.88 (1)	1.93 (2)	2.783 (3)	162 (3)
N15—H15A···Cl1^v	0.88 (1)	2.61 (2)	3.367 (3)	145 (3)
N15—H15B···O11	0.88 (1)	2.03 (3)	2.688 (3)	131 (3)
O1M—H1M···Cl1	0.84	2.26	3.091 (2)	171
O2M—H2M···O1M	0.84	1.91	2.745 (3)	170

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+1/2, y−1/2, −z+1/2; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₆H₉ClN₇O⁺·Cl⁻·2CH₄O
M_r	330.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	5.9473 (5), 16.7278 (17), 14.7784 (15)
β (°)	90.080 (8)
V (Å³)	1470.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Stoe IPDS II two-circle
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.874, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	19184, 2739, 1852
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.080, 0.96
No. of reflections	2739
No. of parameters	212
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.25

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N31—H31A···N4ⁱ	0.880 (10)	2.137 (13)	2.996 (3)	165 (3)
N31—H31B···Cl1ⁱⁱ	0.872 (10)	2.497 (18)	3.281 (3)	150 (3)
N51—H51A···Cl1ⁱⁱⁱ	0.879 (10)	2.540 (13)	3.396 (3)	165 (3)
N51—H51B···O11	0.878 (10)	2.11 (2)	2.781 (3)	133 (3)
N12—H12···O2M^iv	0.866 (10)	2.137 (18)	2.912 (3)	149 (3)
N14—H14A···Cl1^v	0.880 (10)	2.341 (14)	3.188 (3)	162 (3)
N14—H14B···O2M^iv	0.884 (10)	1.930 (15)	2.783 (3)	162 (3)
N15—H15A···Cl1^v	0.880 (10)	2.61 (2)	3.367 (3)	145 (3)
N15—H15B···O11	0.876 (10)	2.03 (3)	2.688 (3)	131 (3)
O1M—H1M···Cl1	0.84	2.26	3.091 (2)	171.3
O2M—H2M···O1M	0.84	1.91	2.745 (3)	170.1

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+1/2, y−1/2, −z+1/2; (v) x−1, y, z.

References

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