organic compounds
(2E)-1-Phenyl-2-[1-(2-phenylprop-2-en-1-yl)pyrrolidin-2-ylidene]ethanone
aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO WITS, 2050, Johannesburg, South Africa
*Correspondence e-mail: joseph.michael@wits.ac.za
The title compound, C21H21NO, is a vinylogous amide (enaminone) produced by reaction of 1-(2-phenylprop-2-en-1-yl)pyrrolidine-2-thione with phenacyl bromide. In the molecule, the phenyl rings are twisted from the mean plane of the pyrrolidine ring by 11.2 (1) and 67.3 (1)°. In the crystal, weak C—H⋯O hydrogen bonds link the molecules related by translation along the b axis into chains.
Related literature
For details of the synthesis of enaminones, see: Roth et al. (1971). For applications of enaminones in alkaloid synthesis, see: Michael et al. (1999). For a related enaminone structure, see: Lemmerer et al. (2007).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812044443/cv5350sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812044443/cv5350Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812044443/cv5350Isup3.mol
Supporting information file. DOI: 10.1107/S1600536812044443/cv5350Isup4.cml
The synthesis employed followed the Eschenmoser procedure (Roth et al., 1971). A solution of phenacyl bromide (4.30 g, 21.6 mmol) and 1-(2-phenylprop-2-en-1-yl)pyrrolidine-2-thione (4.27 g, 19.6 mmol) in dry acetonitrile (20 ml) was stirred at room temperature under an argon atmosphere until precipitation of the adduct as a gum was complete. The mixture was briefly warmed to solubilize the precipitate, after which a solution of triphenylphosphine (5.66 g, 21.6 mmol) and triethylamine (3.31 ml, 23.6 mmol) in dry MeCN (20 ml) was added dropwise to induce extrusion of sulfur, and stirring was maintained for 18 h. The solvent was evaporated and the residue was taken up into ethyl acetate (200 ml) and washed with water (3 × 100 ml) and brine (50 ml). The organic phase was dried over MgSO4, filtered and evaporated to give an orange gum.
on silica gel with hexane:ethyl acetate (3:2 v/v) afforded the title compound (5.42 g, 91%) as very pale yellow needles, m.p. 325—326 K.The C-bound H atoms were geometrically positioned [C—H = 0.93 Å (alkenyl- and aromatic-H) and 0.97 Å (methylene-H)] and refined as riding with Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous scatterers in the molecule, 1562 Friedel pairs were merged before the final refinement.
Data collection: APEX2 (Bruker, 2005); cell
SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).C21H21NO | Z = 1 |
Mr = 303.39 | F(000) = 162 |
Triclinic, P1 | Dx = 1.188 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.7806 (6) Å | Cell parameters from 1287 reflections |
b = 7.9407 (7) Å | θ = 2.2–24.8° |
c = 9.6089 (9) Å | µ = 0.07 mm−1 |
α = 82.579 (7)° | T = 293 K |
β = 76.793 (7)° | Prism, colourless |
γ = 83.510 (7)° | 0.4 × 0.2 × 0.19 mm |
V = 424.21 (7) Å3 |
Bruker APEXII CCD area-detector diffractometer | Rint = 0.040 |
ω scans | θmax = 25.5°, θmin = 2.2° |
5222 measured reflections | h = −6→6 |
1563 independent reflections | k = −9→9 |
970 reflections with I > 2σ(I) | l = −11→11 |
Refinement on F2 | 3 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0653P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.119 | (Δ/σ)max < 0.001 |
S = 0.98 | Δρmax = 0.11 e Å−3 |
1563 reflections | Δρmin = −0.13 e Å−3 |
208 parameters |
C21H21NO | γ = 83.510 (7)° |
Mr = 303.39 | V = 424.21 (7) Å3 |
Triclinic, P1 | Z = 1 |
a = 5.7806 (6) Å | Mo Kα radiation |
b = 7.9407 (7) Å | µ = 0.07 mm−1 |
c = 9.6089 (9) Å | T = 293 K |
α = 82.579 (7)° | 0.4 × 0.2 × 0.19 mm |
β = 76.793 (7)° |
Bruker APEXII CCD area-detector diffractometer | 970 reflections with I > 2σ(I) |
5222 measured reflections | Rint = 0.040 |
1563 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 3 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.11 e Å−3 |
1563 reflections | Δρmin = −0.13 e Å−3 |
208 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 | 0.6399 (6) | 0.8328 (4) | 1.0527 (4) | 0.0522 (9) | |
C2 | 0.5691 (7) | 1.0058 (4) | 1.0341 (4) | 0.0653 (11) | |
H2 | 0.446 | 1.0433 | 0.9869 | 0.078* | |
C3 | 0.6799 (8) | 1.1226 (5) | 1.0850 (5) | 0.0752 (12) | |
H3 | 0.6316 | 1.2382 | 1.0718 | 0.09* | |
C4 | 0.8608 (8) | 1.0687 (6) | 1.1548 (5) | 0.0785 (13) | |
H4 | 0.9371 | 1.1472 | 1.1881 | 0.094* | |
C5 | 0.9283 (7) | 0.8981 (6) | 1.1751 (5) | 0.0789 (13) | |
H5 | 1.0501 | 0.8604 | 1.2233 | 0.095* | |
C6 | 0.8181 (7) | 0.7835 (5) | 1.1250 (4) | 0.0659 (11) | |
H6 | 0.8656 | 0.668 | 1.1406 | 0.079* | |
C7 | 0.5255 (7) | 0.6979 (4) | 1.0017 (4) | 0.0636 (11) | |
C8 | 0.3853 (7) | 0.7440 (4) | 0.8977 (4) | 0.0585 (10) | |
H8 | 0.3737 | 0.8574 | 0.8591 | 0.07* | |
C9 | 0.2666 (7) | 0.6322 (5) | 0.8508 (4) | 0.0636 (11) | |
C10 | 0.2782 (9) | 0.4424 (5) | 0.8878 (5) | 0.0838 (13) | |
H10A | 0.2124 | 0.4137 | 0.9893 | 0.101* | |
H10B | 0.4419 | 0.3929 | 0.8653 | 0.101* | |
C11 | 0.1326 (11) | 0.3781 (7) | 0.7980 (7) | 0.1127 (19) | |
H11A | 0.2347 | 0.3109 | 0.7267 | 0.135* | |
H11B | 0.0148 | 0.3068 | 0.8582 | 0.135* | |
C12 | 0.0139 (10) | 0.5276 (7) | 0.7269 (6) | 0.1016 (17) | |
H12A | −0.1575 | 0.5333 | 0.7633 | 0.122* | |
H12B | 0.0477 | 0.5234 | 0.6238 | 0.122* | |
C13 | 0.0360 (8) | 0.8452 (6) | 0.7109 (4) | 0.0773 (12) | |
H13A | 0.0421 | 0.9211 | 0.7811 | 0.093* | |
H13B | −0.1294 | 0.8469 | 0.7046 | 0.093* | |
C14 | 0.1767 (8) | 0.9137 (6) | 0.5674 (4) | 0.0778 (12) | |
C15 | 0.0892 (8) | 1.0875 (6) | 0.5101 (4) | 0.0751 (12) | |
C16 | −0.1450 (9) | 1.1520 (6) | 0.5513 (6) | 0.0909 (14) | |
H16 | −0.2506 | 1.0866 | 0.6185 | 0.109* | |
C17 | −0.2279 (11) | 1.3117 (8) | 0.4954 (7) | 0.1099 (17) | |
H17 | −0.3873 | 1.3518 | 0.5237 | 0.132* | |
C18 | −0.0743 (16) | 1.4078 (8) | 0.3995 (7) | 0.1170 (19) | |
H18 | −0.1294 | 1.5144 | 0.3614 | 0.14* | |
C19 | 0.1563 (17) | 1.3526 (10) | 0.3579 (6) | 0.121 (2) | |
H19 | 0.2612 | 1.422 | 0.2942 | 0.145* | |
C20 | 0.2381 (9) | 1.1892 (8) | 0.4114 (5) | 0.1007 (17) | |
H20 | 0.3965 | 1.1492 | 0.3792 | 0.121* | |
C21 | 0.3663 (10) | 0.8275 (8) | 0.4994 (6) | 0.1161 (19) | |
H21A | 0.4527 | 0.8741 | 0.4117 | 0.139* | |
H21B | 0.4147 | 0.7197 | 0.5389 | 0.139* | |
O1 | 0.5650 (7) | 0.5495 (3) | 1.0546 (4) | 0.0998 (11) | |
N1 | 0.1148 (6) | 0.6753 (4) | 0.7626 (3) | 0.0725 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.067 (2) | 0.0394 (18) | 0.049 (2) | −0.0063 (17) | −0.0088 (18) | −0.0052 (16) |
C2 | 0.081 (3) | 0.041 (2) | 0.076 (3) | −0.004 (2) | −0.019 (2) | −0.0123 (18) |
C3 | 0.094 (3) | 0.048 (2) | 0.086 (3) | −0.011 (2) | −0.016 (3) | −0.018 (2) |
C4 | 0.086 (3) | 0.078 (3) | 0.077 (3) | −0.024 (3) | −0.012 (3) | −0.027 (2) |
C5 | 0.074 (3) | 0.089 (3) | 0.079 (3) | −0.004 (3) | −0.022 (2) | −0.019 (3) |
C6 | 0.080 (3) | 0.052 (2) | 0.065 (3) | −0.003 (2) | −0.015 (2) | −0.0099 (19) |
C7 | 0.089 (3) | 0.044 (2) | 0.058 (3) | −0.007 (2) | −0.012 (2) | −0.0082 (19) |
C8 | 0.074 (2) | 0.044 (2) | 0.057 (2) | −0.0108 (19) | −0.009 (2) | −0.0080 (18) |
C9 | 0.074 (3) | 0.063 (2) | 0.054 (2) | −0.017 (2) | −0.002 (2) | −0.017 (2) |
C10 | 0.111 (3) | 0.058 (2) | 0.088 (3) | −0.024 (2) | −0.015 (3) | −0.023 (2) |
C11 | 0.135 (5) | 0.097 (4) | 0.118 (5) | −0.047 (4) | −0.020 (4) | −0.034 (4) |
C12 | 0.107 (4) | 0.113 (4) | 0.097 (4) | −0.035 (3) | −0.019 (3) | −0.043 (3) |
C13 | 0.069 (3) | 0.101 (3) | 0.065 (3) | −0.009 (2) | −0.015 (2) | −0.017 (2) |
C14 | 0.072 (3) | 0.106 (3) | 0.055 (2) | −0.022 (2) | −0.011 (2) | −0.001 (2) |
C15 | 0.077 (3) | 0.108 (3) | 0.048 (2) | −0.032 (3) | −0.015 (2) | −0.014 (2) |
C16 | 0.091 (4) | 0.091 (3) | 0.094 (3) | −0.023 (3) | −0.022 (3) | −0.004 (3) |
C17 | 0.125 (5) | 0.108 (4) | 0.112 (5) | −0.010 (4) | −0.052 (4) | −0.021 (4) |
C18 | 0.172 (7) | 0.113 (5) | 0.083 (4) | −0.042 (5) | −0.049 (4) | −0.009 (4) |
C19 | 0.179 (7) | 0.126 (5) | 0.064 (4) | −0.078 (5) | −0.019 (4) | 0.010 (3) |
C20 | 0.107 (4) | 0.145 (5) | 0.055 (3) | −0.051 (4) | −0.005 (3) | −0.015 (3) |
C21 | 0.108 (4) | 0.129 (4) | 0.085 (3) | 0.000 (3) | 0.025 (3) | −0.007 (3) |
O1 | 0.165 (3) | 0.0361 (15) | 0.114 (3) | −0.0150 (15) | −0.065 (2) | 0.0006 (14) |
N1 | 0.082 (2) | 0.075 (2) | 0.067 (2) | −0.0187 (19) | −0.018 (2) | −0.0181 (18) |
C1—C6 | 1.365 (5) | C11—H11B | 0.97 |
C1—C2 | 1.389 (4) | C12—N1 | 1.478 (6) |
C1—C7 | 1.507 (5) | C12—H12A | 0.97 |
C2—C3 | 1.380 (5) | C12—H12B | 0.97 |
C2—H2 | 0.93 | C13—N1 | 1.437 (5) |
C3—C4 | 1.368 (6) | C13—C14 | 1.501 (6) |
C3—H3 | 0.93 | C13—H13A | 0.97 |
C4—C5 | 1.368 (6) | C13—H13B | 0.97 |
C4—H4 | 0.93 | C14—C21 | 1.309 (6) |
C5—C6 | 1.360 (6) | C14—C15 | 1.495 (6) |
C5—H5 | 0.93 | C15—C20 | 1.371 (6) |
C6—H6 | 0.93 | C15—C16 | 1.379 (6) |
C7—O1 | 1.239 (4) | C16—C17 | 1.390 (7) |
C7—C8 | 1.413 (5) | C16—H16 | 0.93 |
C8—C9 | 1.358 (5) | C17—C18 | 1.348 (8) |
C8—H8 | 0.93 | C17—H17 | 0.93 |
C9—N1 | 1.342 (5) | C18—C19 | 1.341 (8) |
C9—C10 | 1.500 (5) | C18—H18 | 0.93 |
C10—C11 | 1.503 (7) | C19—C20 | 1.404 (8) |
C10—H10A | 0.97 | C19—H19 | 0.93 |
C10—H10B | 0.97 | C20—H20 | 0.93 |
C11—C12 | 1.472 (7) | C21—H21A | 0.93 |
C11—H11A | 0.97 | C21—H21B | 0.93 |
C6—C1—C2 | 117.7 (3) | C11—C12—N1 | 104.6 (4) |
C6—C1—C7 | 118.8 (3) | C11—C12—H12A | 110.8 |
C2—C1—C7 | 123.5 (3) | N1—C12—H12A | 110.8 |
C3—C2—C1 | 120.5 (4) | C11—C12—H12B | 110.8 |
C3—C2—H2 | 119.7 | N1—C12—H12B | 110.8 |
C1—C2—H2 | 119.7 | H12A—C12—H12B | 108.9 |
C4—C3—C2 | 120.2 (4) | N1—C13—C14 | 115.3 (4) |
C4—C3—H3 | 119.9 | N1—C13—H13A | 108.5 |
C2—C3—H3 | 119.9 | C14—C13—H13A | 108.5 |
C3—C4—C5 | 119.4 (4) | N1—C13—H13B | 108.5 |
C3—C4—H4 | 120.3 | C14—C13—H13B | 108.5 |
C5—C4—H4 | 120.3 | H13A—C13—H13B | 107.5 |
C6—C5—C4 | 120.2 (4) | C21—C14—C15 | 122.8 (4) |
C6—C5—H5 | 119.9 | C21—C14—C13 | 121.7 (5) |
C4—C5—H5 | 119.9 | C15—C14—C13 | 115.5 (4) |
C5—C6—C1 | 122.0 (4) | C20—C15—C16 | 116.7 (5) |
C5—C6—H6 | 119 | C20—C15—C14 | 121.3 (4) |
C1—C6—H6 | 119 | C16—C15—C14 | 122.0 (4) |
O1—C7—C8 | 123.9 (3) | C15—C16—C17 | 122.0 (5) |
O1—C7—C1 | 116.2 (4) | C15—C16—H16 | 119 |
C8—C7—C1 | 119.9 (3) | C17—C16—H16 | 119 |
C9—C8—C7 | 123.8 (3) | C18—C17—C16 | 119.1 (6) |
C9—C8—H8 | 118.1 | C18—C17—H17 | 120.5 |
C7—C8—H8 | 118.1 | C16—C17—H17 | 120.5 |
N1—C9—C8 | 124.8 (3) | C19—C18—C17 | 121.3 (6) |
N1—C9—C10 | 108.2 (3) | C19—C18—H18 | 119.3 |
C8—C9—C10 | 127.0 (4) | C17—C18—H18 | 119.3 |
C9—C10—C11 | 105.7 (4) | C18—C19—C20 | 119.5 (6) |
C9—C10—H10A | 110.6 | C18—C19—H19 | 120.3 |
C11—C10—H10A | 110.6 | C20—C19—H19 | 120.3 |
C9—C10—H10B | 110.6 | C15—C20—C19 | 121.3 (6) |
C11—C10—H10B | 110.6 | C15—C20—H20 | 119.4 |
H10A—C10—H10B | 108.7 | C19—C20—H20 | 119.4 |
C12—C11—C10 | 107.5 (4) | C14—C21—H21A | 120 |
C12—C11—H11A | 110.2 | C14—C21—H21B | 120 |
C10—C11—H11A | 110.2 | H21A—C21—H21B | 120 |
C12—C11—H11B | 110.2 | C9—N1—C13 | 126.6 (3) |
C10—C11—H11B | 110.2 | C9—N1—C12 | 113.4 (4) |
H11A—C11—H11B | 108.5 | C13—N1—C12 | 119.8 (4) |
C6—C1—C2—C3 | 1.3 (5) | N1—C13—C14—C15 | 177.5 (3) |
C7—C1—C2—C3 | 179.2 (4) | C21—C14—C15—C20 | −21.8 (7) |
C1—C2—C3—C4 | −0.2 (6) | C13—C14—C15—C20 | 156.6 (4) |
C2—C3—C4—C5 | −0.8 (6) | C21—C14—C15—C16 | 156.8 (5) |
C3—C4—C5—C6 | 0.6 (7) | C13—C14—C15—C16 | −24.7 (5) |
C4—C5—C6—C1 | 0.5 (6) | C20—C15—C16—C17 | 0.4 (6) |
C2—C1—C6—C5 | −1.5 (6) | C14—C15—C16—C17 | −178.3 (4) |
C7—C1—C6—C5 | −179.5 (4) | C15—C16—C17—C18 | −1.0 (7) |
C6—C1—C7—O1 | 14.8 (5) | C16—C17—C18—C19 | −0.4 (8) |
C2—C1—C7—O1 | −163.2 (4) | C17—C18—C19—C20 | 2.2 (8) |
C6—C1—C7—C8 | −164.4 (4) | C16—C15—C20—C19 | 1.5 (6) |
C2—C1—C7—C8 | 17.7 (5) | C14—C15—C20—C19 | −179.8 (4) |
O1—C7—C8—C9 | 4.2 (6) | C18—C19—C20—C15 | −2.8 (8) |
C1—C7—C8—C9 | −176.7 (3) | C8—C9—N1—C13 | −5.1 (6) |
C7—C8—C9—N1 | 173.4 (4) | C10—C9—N1—C13 | 174.4 (4) |
C7—C8—C9—C10 | −6.0 (6) | C8—C9—N1—C12 | 179.0 (4) |
N1—C9—C10—C11 | 5.6 (5) | C10—C9—N1—C12 | −1.5 (5) |
C8—C9—C10—C11 | −174.9 (4) | C14—C13—N1—C9 | 94.1 (4) |
C9—C10—C11—C12 | −7.5 (5) | C14—C13—N1—C12 | −90.3 (5) |
C10—C11—C12—N1 | 6.6 (5) | C11—C12—N1—C9 | −3.3 (5) |
N1—C13—C14—C21 | −4.0 (6) | C11—C12—N1—C13 | −179.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.93 | 2.45 | 3.368 (5) | 170 |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C21H21NO |
Mr | 303.39 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 5.7806 (6), 7.9407 (7), 9.6089 (9) |
α, β, γ (°) | 82.579 (7), 76.793 (7), 83.510 (7) |
V (Å3) | 424.21 (7) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.4 × 0.2 × 0.19 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5222, 1563, 970 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.605 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.119, 0.98 |
No. of reflections | 1563 |
No. of parameters | 208 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.11, −0.13 |
Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.93 | 2.45 | 3.368 (5) | 170 |
Symmetry code: (i) x, y+1, z. |
Acknowledgements
This research was supported by the University of the Witwatersrand and the Molecular Sciences Institute, which are thanked for providing the infrastructure required to do this work.
References
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The title compound, (2E)-1-phenyl-2-[1-(2-phenylprop-2-en-1-yl)pyrrolidin-2-ylidene] ethanone, (I), was prepared as part of an ongoing project dealing with the use of enaminones as intermediates for alkaloid synthesis (Michael et al., 1999).
In (I) (Fig. 1), two phenyl rings are twisted from the mean plane of the central pyrrolidine ring by 11.2 (1) and 67.3 (1)°, respectively. The (E) configuration and s-cis conformation of the exocyclic C═C bond of the enaminone are similar to those found in a related enaminone (Lemmerer et al., 2007). In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules related by translation along the b axis into chains (Fig. 2).