Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013394/na6244sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013394/na6244Isup2.hkl |
CCDC reference: 217603
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.111
- Data-to-parameter ratio = 17.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
2-Phenyl-1,3-bis(2-pyridylmethyl)imidazolidine was prepared according to a literature method (Baffert et al., 2003). Colourless block-shaped single crystals suitable were grown by slow evaporation of a dichloromethane solution.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).
C21H22N4 | F(000) = 704 |
Mr = 330.43 | Dx = 1.253 Mg m−3 |
Monoclinic, P21/n | Melting point = 415–419 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71069 Å |
a = 6.003 (5) Å | Cell parameters from 22931 reflections |
b = 15.175 (5) Å | θ = 2.7–26.2° |
c = 19.237 (5) Å | µ = 0.08 mm−1 |
β = 91.794 (5)° | T = 120 K |
V = 1751.5 (16) Å3 | Block, colourless |
Z = 4 | 0.45 × 0.25 × 0.1 mm |
Bruker SMART CCD diffractometer | 2464 reflections with I > 2σ(I) |
ω rotation scans | Rint = 0.083 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 27.5°, θmin = 1.7° |
Tmin = 0.883, Tmax = 0.992 | h = −7→7 |
20244 measured reflections | k = −19→19 |
4019 independent reflections | l = −24→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0464P)2 + 0.1083P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
4019 reflections | Δρmax = 0.24 e Å−3 |
227 parameters | Δρmin = −0.2 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0053 (8) |
C21H22N4 | V = 1751.5 (16) Å3 |
Mr = 330.43 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.003 (5) Å | µ = 0.08 mm−1 |
b = 15.175 (5) Å | T = 120 K |
c = 19.237 (5) Å | 0.45 × 0.25 × 0.1 mm |
β = 91.794 (5)° |
Bruker SMART CCD diffractometer | 4019 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2464 reflections with I > 2σ(I) |
Tmin = 0.883, Tmax = 0.992 | Rint = 0.083 |
20244 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.24 e Å−3 |
4019 reflections | Δρmin = −0.2 e Å−3 |
227 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2844 (3) | 0.04647 (11) | 0.18605 (8) | 0.0260 (4) | |
H1A | 0.1993 | −0.0068 | 0.1986 | 0.031* | |
H1B | 0.4346 | 0.0434 | 0.2087 | 0.031* | |
C2 | 0.3002 (3) | 0.05436 (11) | 0.10745 (8) | 0.0236 (4) | |
H2A | 0.4575 | 0.0594 | 0.0939 | 0.028* | |
H2B | 0.232 | 0.0026 | 0.0838 | 0.028* | |
C3 | 0.0262 (3) | 0.15051 (10) | 0.14702 (8) | 0.0180 (4) | |
H3 | −0.1054 | 0.1102 | 0.143 | 0.022* | |
C11 | 0.0466 (3) | 0.11771 (11) | 0.27076 (8) | 0.0216 (4) | |
H11A | −0.0382 | 0.0617 | 0.2692 | 0.026* | |
H11B | −0.062 | 0.1665 | 0.2736 | 0.026* | |
C12 | 0.1960 (3) | 0.11853 (10) | 0.33514 (8) | 0.0189 (4) | |
C13 | 0.4076 (3) | 0.15388 (11) | 0.33586 (9) | 0.0231 (4) | |
H13 | 0.4666 | 0.1775 | 0.2946 | 0.028* | |
C14 | 0.5330 (3) | 0.15462 (11) | 0.39737 (9) | 0.0285 (4) | |
H14 | 0.6796 | 0.1783 | 0.3989 | 0.034* | |
C15 | 0.4416 (3) | 0.12039 (12) | 0.45635 (9) | 0.0306 (5) | |
H15 | 0.523 | 0.1204 | 0.4995 | 0.037* | |
C16 | 0.2294 (3) | 0.08624 (12) | 0.45123 (9) | 0.0308 (5) | |
H16 | 0.167 | 0.0626 | 0.492 | 0.037* | |
C21 | 0.0582 (3) | 0.13274 (11) | 0.02272 (8) | 0.0221 (4) | |
H21A | −0.0497 | 0.1821 | 0.02 | 0.026* | |
H21B | −0.0273 | 0.0771 | 0.0191 | 0.026* | |
C22 | 0.2104 (3) | 0.13883 (10) | −0.03784 (8) | 0.0196 (4) | |
C23 | 0.4226 (3) | 0.17400 (11) | −0.03124 (9) | 0.0236 (4) | |
H23 | 0.4807 | 0.1926 | 0.0129 | 0.028* | |
C24 | 0.5488 (3) | 0.18162 (11) | −0.08975 (9) | 0.0280 (4) | |
H24 | 0.6954 | 0.2051 | −0.0864 | 0.034* | |
C25 | 0.4592 (3) | 0.15483 (11) | −0.15283 (9) | 0.0285 (4) | |
H25 | 0.5411 | 0.16 | −0.1941 | 0.034* | |
C26 | 0.2481 (3) | 0.12041 (12) | −0.15444 (9) | 0.0325 (5) | |
H26 | 0.187 | 0.1017 | −0.1981 | 0.039* | |
C31 | −0.0492 (3) | 0.24523 (11) | 0.14910 (8) | 0.0182 (4) | |
C32 | 0.1092 (3) | 0.31028 (11) | 0.16163 (8) | 0.0229 (4) | |
H32 | 0.2595 | 0.2941 | 0.1719 | 0.027* | |
C33 | 0.0513 (3) | 0.39829 (11) | 0.15932 (9) | 0.0262 (4) | |
H33 | 0.1611 | 0.4423 | 0.168 | 0.031* | |
C34 | −0.1676 (3) | 0.42206 (11) | 0.14433 (8) | 0.0276 (4) | |
H34 | −0.2078 | 0.4826 | 0.1418 | 0.033* | |
C35 | −0.3260 (3) | 0.35831 (11) | 0.13308 (9) | 0.0284 (4) | |
H35 | −0.4763 | 0.3748 | 0.1232 | 0.034* | |
C36 | −0.2681 (3) | 0.26934 (11) | 0.13606 (8) | 0.0237 (4) | |
H36 | −0.3794 | 0.2254 | 0.1291 | 0.028* | |
N1 | 0.1676 (2) | 0.12666 (8) | 0.20699 (7) | 0.0189 (3) | |
N2 | 0.1755 (2) | 0.13554 (8) | 0.08983 (7) | 0.0191 (3) | |
N11 | 0.1054 (2) | 0.08435 (9) | 0.39190 (7) | 0.0245 (4) | |
N21 | 0.1221 (3) | 0.11135 (9) | −0.09878 (7) | 0.0277 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0327 (11) | 0.0233 (9) | 0.0219 (9) | 0.0075 (8) | 0.0014 (8) | 0.0004 (8) |
C2 | 0.0272 (10) | 0.0214 (9) | 0.0224 (9) | 0.0035 (8) | 0.0029 (8) | 0.0005 (7) |
C3 | 0.0197 (9) | 0.0185 (9) | 0.0156 (8) | −0.0028 (7) | 0.0003 (7) | −0.0005 (7) |
C11 | 0.0222 (10) | 0.0225 (9) | 0.0200 (9) | −0.0033 (8) | 0.0016 (7) | 0.0001 (7) |
C12 | 0.0223 (9) | 0.0160 (8) | 0.0185 (9) | 0.0019 (7) | 0.0022 (7) | −0.0014 (7) |
C13 | 0.0263 (10) | 0.0217 (9) | 0.0215 (9) | 0.0014 (8) | 0.0018 (8) | −0.0011 (7) |
C14 | 0.0275 (11) | 0.0262 (10) | 0.0316 (11) | 0.0035 (8) | −0.0026 (9) | −0.0079 (8) |
C15 | 0.0362 (12) | 0.0333 (11) | 0.0216 (10) | 0.0052 (9) | −0.0071 (9) | −0.0028 (8) |
C16 | 0.0425 (12) | 0.0320 (10) | 0.0179 (9) | −0.0015 (9) | 0.0002 (8) | 0.0025 (8) |
C21 | 0.0235 (10) | 0.0241 (9) | 0.0185 (9) | −0.0012 (8) | −0.0016 (7) | −0.0010 (7) |
C22 | 0.0249 (10) | 0.0158 (9) | 0.0181 (9) | 0.0022 (7) | 0.0000 (7) | 0.0008 (7) |
C23 | 0.0256 (10) | 0.0265 (10) | 0.0186 (9) | −0.0008 (8) | −0.0018 (8) | 0.0016 (7) |
C24 | 0.0257 (10) | 0.0281 (10) | 0.0302 (10) | 0.0006 (8) | 0.0022 (8) | 0.0090 (8) |
C25 | 0.0362 (12) | 0.0264 (10) | 0.0235 (10) | 0.0030 (9) | 0.0099 (9) | 0.0038 (8) |
C26 | 0.0450 (13) | 0.0335 (11) | 0.0192 (10) | −0.0034 (10) | 0.0038 (9) | −0.0044 (8) |
C31 | 0.0227 (10) | 0.0215 (9) | 0.0106 (8) | −0.0016 (7) | 0.0027 (7) | −0.0010 (7) |
C32 | 0.0255 (10) | 0.0234 (9) | 0.0199 (9) | −0.0007 (8) | 0.0015 (7) | 0.0001 (7) |
C33 | 0.0342 (11) | 0.0209 (9) | 0.0237 (10) | −0.0058 (8) | 0.0046 (8) | −0.0028 (7) |
C34 | 0.0375 (12) | 0.0208 (9) | 0.0253 (10) | 0.0061 (9) | 0.0130 (9) | 0.0014 (8) |
C35 | 0.0248 (10) | 0.0305 (11) | 0.0304 (10) | 0.0070 (9) | 0.0085 (8) | 0.0076 (8) |
C36 | 0.0227 (10) | 0.0230 (9) | 0.0255 (10) | −0.0029 (8) | 0.0025 (8) | 0.0030 (8) |
N1 | 0.0223 (8) | 0.0187 (7) | 0.0157 (7) | 0.0023 (6) | 0.0011 (6) | 0.0005 (6) |
N2 | 0.0221 (8) | 0.0194 (7) | 0.0157 (7) | 0.0025 (6) | 0.0004 (6) | −0.0002 (6) |
N11 | 0.0306 (9) | 0.0249 (8) | 0.0182 (8) | −0.0011 (7) | 0.0013 (7) | 0.0003 (6) |
N21 | 0.0340 (9) | 0.0296 (8) | 0.0196 (8) | −0.0043 (7) | 0.0018 (7) | −0.0044 (6) |
C1—N1 | 1.467 (2) | C21—N2 | 1.452 (2) |
C1—C2 | 1.523 (2) | C21—C22 | 1.506 (2) |
C1—H1A | 0.99 | C21—H21A | 0.99 |
C1—H1B | 0.99 | C21—H21B | 0.99 |
C2—N2 | 1.476 (2) | C22—N21 | 1.338 (2) |
C2—H2A | 0.99 | C22—C23 | 1.383 (3) |
C2—H2B | 0.99 | C23—C24 | 1.381 (2) |
C3—N1 | 1.456 (2) | C23—H23 | 0.95 |
C3—N2 | 1.459 (2) | C24—C25 | 1.373 (2) |
C3—C31 | 1.508 (2) | C24—H24 | 0.95 |
C3—H3 | 1 | C25—C26 | 1.370 (3) |
C11—N1 | 1.451 (2) | C25—H25 | 0.95 |
C11—C12 | 1.506 (2) | C26—N21 | 1.337 (2) |
C11—H11A | 0.99 | C26—H26 | 0.95 |
C11—H11B | 0.99 | C31—C36 | 1.380 (3) |
C12—N11 | 1.340 (2) | C31—C32 | 1.387 (2) |
C12—C13 | 1.379 (3) | C32—C33 | 1.380 (2) |
C13—C14 | 1.382 (2) | C32—H32 | 0.95 |
C13—H13 | 0.95 | C33—C34 | 1.384 (3) |
C14—C15 | 1.377 (3) | C33—H33 | 0.95 |
C14—H14 | 0.95 | C34—C35 | 1.369 (2) |
C15—C16 | 1.376 (3) | C34—H34 | 0.95 |
C15—H15 | 0.95 | C35—C36 | 1.395 (2) |
C16—N11 | 1.343 (2) | C35—H35 | 0.95 |
C16—H16 | 0.95 | C36—H36 | 0.95 |
N1—C1—C2 | 104.64 (13) | C22—C21—H21B | 108.9 |
N1—C1—H1A | 110.8 | H21A—C21—H21B | 107.7 |
C2—C1—H1A | 110.8 | N21—C22—C23 | 122.62 (15) |
N1—C1—H1B | 110.8 | N21—C22—C21 | 115.19 (15) |
C2—C1—H1B | 110.8 | C23—C22—C21 | 122.14 (15) |
H1A—C1—H1B | 108.9 | C24—C23—C22 | 118.97 (16) |
N2—C2—C1 | 104.28 (13) | C24—C23—H23 | 120.5 |
N2—C2—H2A | 110.9 | C22—C23—H23 | 120.5 |
C1—C2—H2A | 110.9 | C25—C24—C23 | 119.08 (17) |
N2—C2—H2B | 110.9 | C25—C24—H24 | 120.5 |
C1—C2—H2B | 110.9 | C23—C24—H24 | 120.5 |
H2A—C2—H2B | 108.9 | C26—C25—C24 | 117.97 (17) |
N1—C3—N2 | 101.65 (13) | C26—C25—H25 | 121 |
N1—C3—C31 | 112.57 (13) | C24—C25—H25 | 121 |
N2—C3—C31 | 111.13 (12) | N21—C26—C25 | 124.54 (17) |
N1—C3—H3 | 110.4 | N21—C26—H26 | 117.7 |
N2—C3—H3 | 110.4 | C25—C26—H26 | 117.7 |
C31—C3—H3 | 110.4 | C36—C31—C32 | 119.16 (16) |
N1—C11—C12 | 113.17 (14) | C36—C31—C3 | 122.21 (15) |
N1—C11—H11A | 108.9 | C32—C31—C3 | 118.57 (15) |
C12—C11—H11A | 108.9 | C33—C32—C31 | 120.81 (17) |
N1—C11—H11B | 108.9 | C33—C32—H32 | 119.6 |
C12—C11—H11B | 108.9 | C31—C32—H32 | 119.6 |
H11A—C11—H11B | 107.8 | C32—C33—C34 | 119.70 (16) |
N11—C12—C13 | 122.69 (16) | C32—C33—H33 | 120.2 |
N11—C12—C11 | 114.87 (15) | C34—C33—H33 | 120.2 |
C13—C12—C11 | 122.43 (15) | C35—C34—C33 | 119.93 (17) |
C12—C13—C14 | 119.26 (17) | C35—C34—H34 | 120 |
C12—C13—H13 | 120.4 | C33—C34—H34 | 120 |
C14—C13—H13 | 120.4 | C34—C35—C36 | 120.44 (17) |
C15—C14—C13 | 118.78 (18) | C34—C35—H35 | 119.8 |
C15—C14—H14 | 120.6 | C36—C35—H35 | 119.8 |
C13—C14—H14 | 120.6 | C31—C36—C35 | 119.92 (16) |
C16—C15—C14 | 118.37 (17) | C31—C36—H36 | 120 |
C16—C15—H15 | 120.8 | C35—C36—H36 | 120 |
C14—C15—H15 | 120.8 | C11—N1—C3 | 113.45 (13) |
N11—C16—C15 | 123.79 (17) | C11—N1—C1 | 114.23 (13) |
N11—C16—H16 | 118.1 | C3—N1—C1 | 105.09 (12) |
C15—C16—H16 | 118.1 | C21—N2—C3 | 112.52 (13) |
N2—C21—C22 | 113.40 (14) | C21—N2—C2 | 114.10 (13) |
N2—C21—H21A | 108.9 | C3—N2—C2 | 106.04 (12) |
C22—C21—H21A | 108.9 | C12—N11—C16 | 117.11 (15) |
N2—C21—H21B | 108.9 | C26—N21—C22 | 116.82 (16) |
N1—C1—C2—N2 | −4.15 (18) | C3—C31—C36—C35 | −174.81 (15) |
N1—C11—C12—N11 | −160.54 (13) | C34—C35—C36—C31 | −1.3 (3) |
N1—C11—C12—C13 | 21.1 (2) | C12—C11—N1—C3 | −163.80 (13) |
N11—C12—C13—C14 | −0.1 (2) | C12—C11—N1—C1 | 75.77 (17) |
C11—C12—C13—C14 | 178.16 (15) | N2—C3—N1—C11 | −167.80 (12) |
C12—C13—C14—C15 | −0.4 (2) | C31—C3—N1—C11 | 73.23 (16) |
C13—C14—C15—C16 | 0.5 (3) | N2—C3—N1—C1 | −42.33 (15) |
C14—C15—C16—N11 | −0.1 (3) | C31—C3—N1—C1 | −161.30 (13) |
N2—C21—C22—N21 | 161.40 (14) | C2—C1—N1—C11 | 153.77 (14) |
N2—C21—C22—C23 | −21.3 (2) | C2—C1—N1—C3 | 28.79 (17) |
N21—C22—C23—C24 | 0.3 (2) | C22—C21—N2—C3 | 166.43 (13) |
C21—C22—C23—C24 | −176.72 (15) | C22—C21—N2—C2 | −72.70 (17) |
C22—C23—C24—C25 | 0.6 (2) | N1—C3—N2—C21 | 165.09 (12) |
C23—C24—C25—C26 | −0.9 (3) | C31—C3—N2—C21 | −74.92 (16) |
C24—C25—C26—N21 | 0.3 (3) | N1—C3—N2—C2 | 39.70 (15) |
N1—C3—C31—C36 | −133.08 (16) | C31—C3—N2—C2 | 159.69 (13) |
N2—C3—C31—C36 | 113.65 (17) | C1—C2—N2—C21 | −146.35 (14) |
N1—C3—C31—C32 | 49.73 (19) | C1—C2—N2—C3 | −21.94 (17) |
N2—C3—C31—C32 | −63.54 (18) | C13—C12—N11—C16 | 0.5 (2) |
C36—C31—C32—C33 | −1.8 (2) | C11—C12—N11—C16 | −177.85 (14) |
C3—C31—C32—C33 | 175.52 (14) | C15—C16—N11—C12 | −0.5 (3) |
C31—C32—C33—C34 | 0.0 (2) | C25—C26—N21—C22 | 0.6 (3) |
C32—C33—C34—C35 | 1.1 (2) | C23—C22—N21—C26 | −0.9 (2) |
C33—C34—C35—C36 | −0.5 (3) | C21—C22—N21—C26 | 176.36 (15) |
C32—C31—C36—C35 | 2.4 (2) |
Experimental details
Crystal data | |
Chemical formula | C21H22N4 |
Mr | 330.43 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 120 |
a, b, c (Å) | 6.003 (5), 15.175 (5), 19.237 (5) |
β (°) | 91.794 (5) |
V (Å3) | 1751.5 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.45 × 0.25 × 0.1 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.883, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20244, 4019, 2464 |
Rint | 0.083 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.111, 1.02 |
No. of reflections | 4019 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.2 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SAINT, SIR97 (Altomare, 1999), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), WinGX (Farrugia, 1999).
C1—N1 | 1.467 (2) | C2—N2 | 1.476 (2) |
C1—C2 | 1.523 (2) | C3—N1 | 1.456 (2) |
N1—C1—C2 | 104.64 (13) | C3—N1—C1 | 105.09 (12) |
N2—C2—C1 | 104.28 (13) | C3—N2—C2 | 106.04 (12) |
N1—C3—N2 | 101.65 (13) |
II | III | IV | |
I | 21.97 (8) | 73.97 (8) | 70.71 (9) |
II | 84.34 (8) | 71.65 (9) | |
III | 85.44 (9) |
Least-squares planes: I N11/C12–C16, II N21/C22–C26, III C31–C36 and IV N1/C1/C2/N2/C3 |
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Subsequent to the publication of some coordination compounds with the ligand N-benzyl-N'-carboxymethyl-N,N'-bis(2-pyridylmethyl)-1,2-ethanediamine (Baffert et al., 2003) we have succeeded in crystallizing the ligand precursor 2-phenyl-1,3-bis(2-pyridylmethyl)imidazolidine, (I).
Fig. 1 shows the molecular structure of (I) with atom-numbering scheme. The five-membered ring is in the envelope conformation with the apex on C3 [ϕ2 = 5.6 (2)°, total ring puckering amplitude Q2 = 0.3974 (16) Å (Cremer & Pople, 1975)]. This has a pseudo-mirror that includes the phenyl ring through C3 and orthogonal to the C1—C2 bond. All three substituents are in equatorial positions and the pyridine rings are oriented in a syn fashion i.e. the two N atoms are both pointing in the same direction as the axial hydrogen on C2. The exact orientations of the central ring and substituents is summarized in table 1 by the dihedral angles formed by least-squares planes through the individual rings.
Extensive C—H···π interactions (closest contact 2.79 Å) exist between the aromatic rings. Short contacts include N1···H36i 3.48 Å, N2···H36i 3.07 Å, N11···H34ii 2.90 Å and N21···H2Biii 2.76 Å [symmetry codes: (i) x + 1, y, z; (ii) x − 1/2, y − 1/2, 1/2 − z; (iii) −x, −y, −z]. The former two result in stacking along the a axis of the unit cell.