In the title compound, C
23H
21N
3Se, the C-bound phenyl ring is almost coplanar with the central five-membered ring [dihedral angle = 2.84 (10)°], but the N-bound benzene ring is inclined [dihedral angle = 47.52 (10)°]. The dihedral angle between the Se-bound rings is 69.24 (9)°. An intramolecular Se

N interaction of 3.0248 (15) Å is noted. In the crystal, C—H

π interactions connect molecules into double layers that stack along the
a axis with no directional interactions between them.
Supporting information
CCDC reference: 1049547
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.063
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 124 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
2 ALERT level G = General information/check it is not something unexpected
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
The compound was prepared in accord with the literature (Deobald et al.,
2011). Crystals were obtained by taking 200 mg of sample into a sample
vial
containing methanol (5 ml) and ethyl acetate (5 ml) and letting it stand at
room temperature.
Carbon-bound H-atoms were placed in calculated positions (C—H = 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation,
with Uiso(H) = 1.2–1.5Ueq(C).
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and
DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).
4-Phenyl-1-{2-[(2,4,6-trimethylphenyl)selanyl]phenyl}-1
H-1,2,3-triazole
top
Crystal data top
C23H21N3Se | F(000) = 856 |
Mr = 418.39 | Dx = 1.451 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.3924 (4) Å | Cell parameters from 4584 reflections |
b = 6.9332 (1) Å | θ = 2.4–29.3° |
c = 12.9204 (2) Å | µ = 1.97 mm−1 |
β = 92.231 (2)° | T = 100 K |
V = 1914.87 (5) Å3 | Prism, colourless |
Z = 4 | 0.20 × 0.15 × 0.10 mm |
Data collection top
Agilent SuperNova CCD diffractometer | 3740 reflections with I > 2σ(I) |
Radiation source: SuperNova (Cu) X-ray Source | Rint = 0.026 |
ω scans | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | h = −25→27 |
Tmin = 0.809, Tmax = 1.000 | k = −8→7 |
9275 measured reflections | l = −16→12 |
4252 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.063 | w = 1/[σ2(Fo2) + (0.0204P)2 + 1.1744P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4252 reflections | Δρmax = 0.38 e Å−3 |
247 parameters | Δρmin = −0.39 e Å−3 |
Crystal data top
C23H21N3Se | V = 1914.87 (5) Å3 |
Mr = 418.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 21.3924 (4) Å | µ = 1.97 mm−1 |
b = 6.9332 (1) Å | T = 100 K |
c = 12.9204 (2) Å | 0.20 × 0.15 × 0.10 mm |
β = 92.231 (2)° | |
Data collection top
Agilent SuperNova CCD diffractometer | 4252 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 3740 reflections with I > 2σ(I) |
Tmin = 0.809, Tmax = 1.000 | Rint = 0.026 |
9275 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.38 e Å−3 |
4252 reflections | Δρmin = −0.39 e Å−3 |
247 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Se | 0.76393 (2) | 0.40426 (3) | 0.12277 (2) | 0.01683 (7) | |
N1 | 0.65328 (7) | 0.6076 (2) | 0.23160 (12) | 0.0130 (3) | |
N2 | 0.65949 (7) | 0.6956 (2) | 0.13866 (12) | 0.0175 (4) | |
N3 | 0.60302 (7) | 0.7185 (2) | 0.09728 (12) | 0.0171 (3) | |
C1 | 0.83935 (8) | 0.2521 (3) | 0.13795 (14) | 0.0132 (4) | |
C2 | 0.84041 (9) | 0.0834 (3) | 0.19790 (14) | 0.0143 (4) | |
C3 | 0.89540 (9) | −0.0249 (3) | 0.20417 (15) | 0.0168 (4) | |
H3 | 0.8966 | −0.1393 | 0.2447 | 0.020* | |
C4 | 0.94859 (9) | 0.0300 (3) | 0.15272 (15) | 0.0181 (4) | |
C5 | 0.94552 (9) | 0.1966 (3) | 0.09317 (15) | 0.0182 (4) | |
H5 | 0.9814 | 0.2347 | 0.0571 | 0.022* | |
C6 | 0.89188 (9) | 0.3100 (3) | 0.08433 (14) | 0.0157 (4) | |
C7 | 0.78440 (9) | 0.0169 (3) | 0.25528 (16) | 0.0192 (4) | |
H7A | 0.7944 | −0.1043 | 0.2912 | 0.029* | |
H7B | 0.7490 | −0.0033 | 0.2060 | 0.029* | |
H7C | 0.7734 | 0.1152 | 0.3060 | 0.029* | |
C8 | 1.00802 (10) | −0.0852 (4) | 0.16441 (17) | 0.0291 (5) | |
H8A | 0.9984 | −0.2228 | 0.1570 | 0.044* | |
H8B | 1.0277 | −0.0615 | 0.2330 | 0.044* | |
H8C | 1.0367 | −0.0464 | 0.1109 | 0.044* | |
C9 | 0.89247 (10) | 0.4894 (3) | 0.01805 (17) | 0.0250 (5) | |
H9A | 0.8830 | 0.6021 | 0.0605 | 0.038* | |
H9B | 0.8609 | 0.4775 | −0.0386 | 0.038* | |
H9C | 0.9339 | 0.5050 | −0.0107 | 0.038* | |
C10 | 0.76174 (8) | 0.4997 (3) | 0.26208 (14) | 0.0130 (4) | |
C11 | 0.81423 (9) | 0.4896 (3) | 0.32961 (14) | 0.0146 (4) | |
H11 | 0.8524 | 0.4401 | 0.3055 | 0.017* | |
C12 | 0.81130 (9) | 0.5511 (3) | 0.43132 (15) | 0.0153 (4) | |
H12 | 0.8473 | 0.5421 | 0.4764 | 0.018* | |
C13 | 0.75617 (9) | 0.6257 (3) | 0.46787 (15) | 0.0163 (4) | |
H13 | 0.7541 | 0.6652 | 0.5381 | 0.020* | |
C14 | 0.70405 (9) | 0.6421 (3) | 0.40097 (15) | 0.0160 (4) | |
H14 | 0.6663 | 0.6954 | 0.4248 | 0.019* | |
C15 | 0.70724 (8) | 0.5805 (3) | 0.29941 (14) | 0.0123 (4) | |
C16 | 0.59254 (8) | 0.5762 (3) | 0.24976 (15) | 0.0145 (4) | |
H16 | 0.5756 | 0.5184 | 0.3091 | 0.017* | |
C17 | 0.56039 (8) | 0.6464 (3) | 0.16345 (15) | 0.0135 (4) | |
C18 | 0.49267 (9) | 0.6540 (3) | 0.13925 (15) | 0.0151 (4) | |
C19 | 0.46969 (9) | 0.7268 (3) | 0.04465 (15) | 0.0198 (4) | |
H19 | 0.4980 | 0.7722 | −0.0047 | 0.024* | |
C20 | 0.40557 (9) | 0.7336 (3) | 0.02211 (16) | 0.0240 (5) | |
H20 | 0.3902 | 0.7846 | −0.0422 | 0.029* | |
C21 | 0.36407 (9) | 0.6660 (3) | 0.09340 (17) | 0.0221 (5) | |
H21 | 0.3203 | 0.6688 | 0.0775 | 0.026* | |
C22 | 0.38639 (9) | 0.5945 (3) | 0.18778 (17) | 0.0223 (4) | |
H22 | 0.3579 | 0.5493 | 0.2369 | 0.027* | |
C23 | 0.45047 (9) | 0.5887 (3) | 0.21079 (16) | 0.0186 (4) | |
H23 | 0.4655 | 0.5399 | 0.2758 | 0.022* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Se | 0.01516 (10) | 0.02217 (11) | 0.01296 (10) | 0.00690 (8) | −0.00215 (7) | −0.00303 (8) |
N1 | 0.0107 (7) | 0.0140 (8) | 0.0142 (8) | 0.0002 (6) | 0.0017 (6) | 0.0018 (7) |
N2 | 0.0137 (8) | 0.0231 (9) | 0.0157 (8) | 0.0002 (7) | 0.0015 (6) | 0.0047 (7) |
N3 | 0.0119 (8) | 0.0213 (9) | 0.0182 (8) | 0.0012 (7) | 0.0001 (6) | 0.0031 (7) |
C1 | 0.0109 (9) | 0.0163 (9) | 0.0121 (9) | 0.0018 (7) | −0.0019 (7) | −0.0050 (8) |
C2 | 0.0144 (9) | 0.0154 (9) | 0.0131 (9) | −0.0029 (8) | 0.0009 (7) | −0.0050 (8) |
C3 | 0.0212 (10) | 0.0146 (9) | 0.0145 (9) | 0.0024 (8) | −0.0002 (8) | −0.0005 (8) |
C4 | 0.0155 (10) | 0.0244 (11) | 0.0141 (9) | 0.0035 (8) | −0.0022 (7) | −0.0044 (8) |
C5 | 0.0133 (9) | 0.0272 (11) | 0.0142 (9) | −0.0034 (8) | 0.0013 (7) | −0.0026 (9) |
C6 | 0.0168 (9) | 0.0168 (10) | 0.0134 (9) | −0.0023 (8) | −0.0002 (7) | −0.0020 (8) |
C7 | 0.0183 (10) | 0.0189 (10) | 0.0208 (10) | −0.0021 (8) | 0.0042 (8) | 0.0006 (9) |
C8 | 0.0208 (11) | 0.0446 (14) | 0.0218 (11) | 0.0143 (10) | 0.0007 (9) | 0.0016 (11) |
C9 | 0.0254 (11) | 0.0257 (11) | 0.0241 (11) | −0.0018 (9) | 0.0027 (9) | 0.0078 (10) |
C10 | 0.0162 (9) | 0.0105 (9) | 0.0124 (9) | −0.0008 (7) | 0.0006 (7) | 0.0003 (8) |
C11 | 0.0122 (9) | 0.0147 (9) | 0.0167 (9) | 0.0008 (7) | 0.0006 (7) | −0.0013 (8) |
C12 | 0.0164 (9) | 0.0138 (9) | 0.0154 (9) | −0.0005 (8) | −0.0034 (7) | 0.0011 (8) |
C13 | 0.0199 (10) | 0.0167 (10) | 0.0125 (9) | −0.0016 (8) | 0.0021 (7) | −0.0013 (8) |
C14 | 0.0134 (9) | 0.0154 (9) | 0.0196 (10) | 0.0012 (7) | 0.0052 (8) | −0.0007 (8) |
C15 | 0.0109 (9) | 0.0096 (9) | 0.0165 (9) | −0.0020 (7) | 0.0005 (7) | 0.0032 (8) |
C16 | 0.0111 (9) | 0.0124 (9) | 0.0201 (10) | 0.0004 (7) | 0.0033 (7) | 0.0009 (8) |
C17 | 0.0122 (9) | 0.0107 (9) | 0.0178 (9) | 0.0007 (7) | 0.0015 (7) | −0.0014 (8) |
C18 | 0.0137 (9) | 0.0116 (9) | 0.0199 (10) | 0.0010 (7) | 0.0005 (8) | −0.0027 (8) |
C19 | 0.0174 (10) | 0.0259 (11) | 0.0162 (10) | 0.0017 (8) | 0.0016 (8) | −0.0032 (9) |
C20 | 0.0196 (10) | 0.0305 (12) | 0.0215 (10) | 0.0059 (9) | −0.0055 (8) | −0.0053 (10) |
C21 | 0.0124 (9) | 0.0234 (11) | 0.0300 (12) | 0.0015 (8) | −0.0042 (8) | −0.0089 (10) |
C22 | 0.0145 (10) | 0.0182 (10) | 0.0344 (12) | −0.0018 (8) | 0.0030 (9) | 0.0016 (10) |
C23 | 0.0151 (9) | 0.0160 (10) | 0.0245 (10) | 0.0005 (8) | −0.0004 (8) | 0.0048 (9) |
Geometric parameters (Å, º) top
Se—C10 | 1.9199 (18) | C9—H9C | 0.9800 |
Se—C1 | 1.9311 (18) | C10—C15 | 1.396 (3) |
N1—C16 | 1.347 (2) | C10—C11 | 1.397 (2) |
N1—N2 | 1.358 (2) | C11—C12 | 1.385 (3) |
N1—C15 | 1.434 (2) | C11—H11 | 0.9500 |
N2—N3 | 1.311 (2) | C12—C13 | 1.387 (3) |
N3—C17 | 1.369 (2) | C12—H12 | 0.9500 |
C1—C6 | 1.402 (3) | C13—C14 | 1.389 (3) |
C1—C2 | 1.403 (3) | C13—H13 | 0.9500 |
C2—C3 | 1.395 (3) | C14—C15 | 1.384 (3) |
C2—C7 | 1.506 (3) | C14—H14 | 0.9500 |
C3—C4 | 1.393 (3) | C16—C17 | 1.376 (3) |
C3—H3 | 0.9500 | C16—H16 | 0.9500 |
C4—C5 | 1.388 (3) | C17—C18 | 1.471 (3) |
C4—C8 | 1.504 (3) | C18—C23 | 1.393 (3) |
C5—C6 | 1.392 (3) | C18—C19 | 1.394 (3) |
C5—H5 | 0.9500 | C19—C20 | 1.392 (3) |
C6—C9 | 1.510 (3) | C19—H19 | 0.9500 |
C7—H7A | 0.9800 | C20—C21 | 1.385 (3) |
C7—H7B | 0.9800 | C20—H20 | 0.9500 |
C7—H7C | 0.9800 | C21—C22 | 1.384 (3) |
C8—H8A | 0.9800 | C21—H21 | 0.9500 |
C8—H8B | 0.9800 | C22—C23 | 1.392 (3) |
C8—H8C | 0.9800 | C22—H22 | 0.9500 |
C9—H9A | 0.9800 | C23—H23 | 0.9500 |
C9—H9B | 0.9800 | | |
| | | |
C10—Se—C1 | 98.26 (8) | C15—C10—C11 | 117.77 (17) |
C16—N1—N2 | 110.77 (15) | C15—C10—Se | 120.88 (13) |
C16—N1—C15 | 129.16 (16) | C11—C10—Se | 121.34 (14) |
N2—N1—C15 | 119.66 (14) | C12—C11—C10 | 120.82 (17) |
N3—N2—N1 | 107.14 (14) | C12—C11—H11 | 119.6 |
N2—N3—C17 | 109.07 (15) | C10—C11—H11 | 119.6 |
C6—C1—C2 | 121.05 (16) | C11—C12—C13 | 120.54 (17) |
C6—C1—Se | 118.43 (14) | C11—C12—H12 | 119.7 |
C2—C1—Se | 120.48 (14) | C13—C12—H12 | 119.7 |
C3—C2—C1 | 118.44 (17) | C12—C13—C14 | 119.42 (18) |
C3—C2—C7 | 119.49 (17) | C12—C13—H13 | 120.3 |
C1—C2—C7 | 122.06 (17) | C14—C13—H13 | 120.3 |
C4—C3—C2 | 121.86 (18) | C15—C14—C13 | 119.79 (17) |
C4—C3—H3 | 119.1 | C15—C14—H14 | 120.1 |
C2—C3—H3 | 119.1 | C13—C14—H14 | 120.1 |
C5—C4—C3 | 118.04 (17) | C14—C15—C10 | 121.60 (17) |
C5—C4—C8 | 121.29 (19) | C14—C15—N1 | 118.08 (16) |
C3—C4—C8 | 120.65 (19) | C10—C15—N1 | 120.30 (16) |
C4—C5—C6 | 122.45 (18) | N1—C16—C17 | 104.89 (16) |
C4—C5—H5 | 118.8 | N1—C16—H16 | 127.6 |
C6—C5—H5 | 118.8 | C17—C16—H16 | 127.6 |
C5—C6—C1 | 118.15 (18) | N3—C17—C16 | 108.13 (16) |
C5—C6—C9 | 119.12 (18) | N3—C17—C18 | 121.92 (17) |
C1—C6—C9 | 122.73 (17) | C16—C17—C18 | 129.94 (18) |
C2—C7—H7A | 109.5 | C23—C18—C19 | 118.95 (17) |
C2—C7—H7B | 109.5 | C23—C18—C17 | 120.39 (17) |
H7A—C7—H7B | 109.5 | C19—C18—C17 | 120.66 (18) |
C2—C7—H7C | 109.5 | C20—C19—C18 | 120.43 (19) |
H7A—C7—H7C | 109.5 | C20—C19—H19 | 119.8 |
H7B—C7—H7C | 109.5 | C18—C19—H19 | 119.8 |
C4—C8—H8A | 109.5 | C21—C20—C19 | 120.09 (19) |
C4—C8—H8B | 109.5 | C21—C20—H20 | 120.0 |
H8A—C8—H8B | 109.5 | C19—C20—H20 | 120.0 |
C4—C8—H8C | 109.5 | C22—C21—C20 | 119.93 (18) |
H8A—C8—H8C | 109.5 | C22—C21—H21 | 120.0 |
H8B—C8—H8C | 109.5 | C20—C21—H21 | 120.0 |
C6—C9—H9A | 109.5 | C21—C22—C23 | 120.1 (2) |
C6—C9—H9B | 109.5 | C21—C22—H22 | 119.9 |
H9A—C9—H9B | 109.5 | C23—C22—H22 | 120.0 |
C6—C9—H9C | 109.5 | C22—C23—C18 | 120.50 (19) |
H9A—C9—H9C | 109.5 | C22—C23—H23 | 119.8 |
H9B—C9—H9C | 109.5 | C18—C23—H23 | 119.8 |
| | | |
C16—N1—N2—N3 | −0.6 (2) | C11—C10—C15—C14 | −2.5 (3) |
C15—N1—N2—N3 | −173.99 (15) | Se—C10—C15—C14 | 177.07 (14) |
N1—N2—N3—C17 | 0.3 (2) | C11—C10—C15—N1 | 175.45 (16) |
C6—C1—C2—C3 | 0.8 (3) | Se—C10—C15—N1 | −4.9 (2) |
Se—C1—C2—C3 | 178.16 (13) | C16—N1—C15—C14 | −43.5 (3) |
C6—C1—C2—C7 | −179.33 (17) | N2—N1—C15—C14 | 128.46 (18) |
Se—C1—C2—C7 | −2.0 (2) | C16—N1—C15—C10 | 138.4 (2) |
C1—C2—C3—C4 | −0.1 (3) | N2—N1—C15—C10 | −49.6 (2) |
C7—C2—C3—C4 | −179.96 (18) | N2—N1—C16—C17 | 0.7 (2) |
C2—C3—C4—C5 | −0.6 (3) | C15—N1—C16—C17 | 173.24 (17) |
C2—C3—C4—C8 | 177.51 (18) | N2—N3—C17—C16 | 0.1 (2) |
C3—C4—C5—C6 | 0.7 (3) | N2—N3—C17—C18 | 179.00 (17) |
C8—C4—C5—C6 | −177.43 (18) | N1—C16—C17—N3 | −0.5 (2) |
C4—C5—C6—C1 | 0.0 (3) | N1—C16—C17—C18 | −179.26 (18) |
C4—C5—C6—C9 | 179.89 (18) | N3—C17—C18—C23 | −176.52 (18) |
C2—C1—C6—C5 | −0.8 (3) | C16—C17—C18—C23 | 2.1 (3) |
Se—C1—C6—C5 | −178.15 (14) | N3—C17—C18—C19 | 3.3 (3) |
C2—C1—C6—C9 | 179.32 (18) | C16—C17—C18—C19 | −178.05 (19) |
Se—C1—C6—C9 | 1.9 (2) | C23—C18—C19—C20 | −0.2 (3) |
C15—C10—C11—C12 | 2.5 (3) | C17—C18—C19—C20 | 179.96 (18) |
Se—C10—C11—C12 | −177.11 (14) | C18—C19—C20—C21 | −0.6 (3) |
C10—C11—C12—C13 | −0.6 (3) | C19—C20—C21—C22 | 1.0 (3) |
C11—C12—C13—C14 | −1.3 (3) | C20—C21—C22—C23 | −0.6 (3) |
C12—C13—C14—C15 | 1.3 (3) | C21—C22—C23—C18 | −0.2 (3) |
C13—C14—C15—C10 | 0.7 (3) | C19—C18—C23—C22 | 0.6 (3) |
C13—C14—C15—N1 | −177.35 (16) | C17—C18—C23—C22 | −179.55 (18) |
Hydrogen-bond geometry (Å, º) topCg1, Cg2 and Cg3 are the centroids of
the C1–C6, C10–C15 and C18–C23 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Cg1i | 0.95 | 2.68 | 3.481 (2) | 143 |
C7—H7a···Cg2ii | 0.98 | 2.61 | 3.492 (2) | 150 |
C16—H16···Cg3iii | 0.95 | 2.66 | 3.399 (2) | 135 |
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) x, y−1, z; (iii) −x+1, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) topCg1, Cg2 and Cg3 are the centroids of
the C1–C6, C10–C15 and C18–C23 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Cg1i | 0.95 | 2.68 | 3.481 (2) | 143 |
C7—H7a···Cg2ii | 0.98 | 2.61 | 3.492 (2) | 150 |
C16—H16···Cg3iii | 0.95 | 2.66 | 3.399 (2) | 135 |
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) x, y−1, z; (iii) −x+1, y−1/2, −z+1/2. |