organic compounds
(S)-(+)-1-(2-Bromophenyl)ethanol
aHarvard University, Department of Chemistry and Chemical Biology, Cambridge, MA 02138, USA
*Correspondence e-mail: staples@chemistry.msu.edu
The title compound, C8H9BrO, crystallizes with two molecules in the The structure displays O—H⋯O hydrogen bonding, generating zigzag chains evolving around a screw axis along [100].
Related literature
For literature on related complexes, see: Angiolini et al. (1995); Venkatachalam et al. (2005). For related literature, see: Staples (2001); Staples & George (2005); Staples & Huang (2002).
Experimental
Crystal data
|
Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536807059260/bg2123sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807059260/bg2123Isup2.hkl
The title compound was purchased from Aldrich and the crystals were grown by a slow evaporation of a dichloromethane solution.
We have been studying the crystallization properties of enantiomeric compounds and their racemic mixtures, as well as the effect of hydrogen bonding on their crystallization behaviour (Staples and Huang, 2002; Staples and George, 2005). In particular we are interested in those compounds that can act as ligands to transition metal complexes (Staples, 2001). In the course of this study we have structurally characterized the tittle compound, C8H9BrO (I). We have also crystallized the enantiomeric compound, R-(-)-2-bromo-alpha-methyl benzylalcohol, which will be reported later.
S-(+)-2-bromo-alpha-methyl benzylalcohol crystallizes with two molecules in the assymmetric unit and presents intermolecular hydrogen bonding, a fact which can dictate the crystallization as well as solvation properties. It is our hope that we can use this compound for further studies of crystallization and coordination chemistry.
The stucture of S-(+)-2-bromo-alpha-methyl benzylalcohol is shown in Fgure 1. The compound exhibits standard bond lengths and angles, similar to those in closely related compounds (Angiolini et al., 1995; Venkatachalam et al.,2005). It displays hydrogen bonding interactions with neighboring molecules (Table 1), to form a linear type of hydrogen bonding structure (Figure 2). The outcome is a zigzag chain structure containing both unique molecules and evolving around a screw axis along [100].
For literature on related complexes, see: Angiolini et al. (1995); Venkatachalam et al. (2005). For related literature, see: Staples (2001); Staples & George (2005); Staples & Huang (2002).
Data collection: SMART (Bruker, 1997); cell
SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).Fig. 1. Thermal ellipsoid plot (50% probability) of the title compound. | |
Fig. 2. Packing diagram of the title compund showing the linear hydrogen bonding interaction. |
C8H9BrO | F(000) = 800 |
Mr = 201.06 | Dx = 1.577 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3839 reflections |
a = 7.3235 (6) Å | θ = 3.0–23.9° |
b = 11.9440 (11) Å | µ = 4.79 mm−1 |
c = 19.3583 (18) Å | T = 193 K |
V = 1693.3 (3) Å3 | Needle, white |
Z = 8 | 0.20 × 0.08 × 0.08 mm |
Bruker SMART CCD area-detector diffractometer | 4195 independent reflections |
Radiation source: normal-focus sealed tube | 3420 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
phi and ω scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | h = −7→9 |
Tmin = 0.434, Tmax = 0.680 | k = −15→12 |
12365 measured reflections | l = −25→21 |
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)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0359P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4195 reflections | Δρmax = 0.67 e Å−3 |
185 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Absolute structure: Flack, 1983, 1788 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.004 (10) |
C8H9BrO | V = 1693.3 (3) Å3 |
Mr = 201.06 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.3235 (6) Å | µ = 4.79 mm−1 |
b = 11.9440 (11) Å | T = 193 K |
c = 19.3583 (18) Å | 0.20 × 0.08 × 0.08 mm |
Bruker SMART CCD area-detector diffractometer | 4195 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | 3420 reflections with I > 2σ(I) |
Tmin = 0.434, Tmax = 0.680 | Rint = 0.027 |
12365 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.080 | Δρmax = 0.67 e Å−3 |
S = 1.03 | Δρmin = −0.33 e Å−3 |
4195 reflections | Absolute structure: Flack, 1983, 1788 Friedel pairs |
185 parameters | Absolute structure parameter: −0.004 (10) |
0 restraints |
Experimental. Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 193 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3° per frame for 30 s, such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.76 Å. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. The structures are solved by the direct method using the SHELX90 program and refined by least squares method on F2 SHELXL93, incorporated in SHELXTL V6.1. |
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. |
x | y | z | Uiso*/Ueq | ||
Br1A | 0.13612 (6) | 0.57908 (3) | 0.20047 (2) | 0.07072 (14) | |
O1A | 0.0096 (3) | 0.29862 (17) | 0.05433 (10) | 0.0494 (5) | |
H1A | 0.1035 | 0.3182 | 0.0326 | 0.074* | |
C1A | 0.2226 (4) | 0.4285 (2) | 0.20561 (15) | 0.0458 (7) | |
C2A | 0.1479 (4) | 0.3466 (2) | 0.16427 (14) | 0.0403 (6) | |
C3A | 0.2190 (5) | 0.2392 (3) | 0.17111 (16) | 0.0553 (8) | |
H3A | 0.1718 | 0.1807 | 0.1431 | 0.066* | |
C4A | 0.3564 (5) | 0.2154 (4) | 0.2175 (2) | 0.0701 (10) | |
H4A | 0.4020 | 0.1413 | 0.2217 | 0.084* | |
C5A | 0.4272 (5) | 0.3004 (4) | 0.25806 (19) | 0.0675 (10) | |
H5A | 0.5222 | 0.2843 | 0.2900 | 0.081* | |
C6A | 0.3622 (4) | 0.4066 (3) | 0.25272 (17) | 0.0606 (9) | |
H6A | 0.4110 | 0.4649 | 0.2806 | 0.073* | |
C7A | −0.0089 (4) | 0.3657 (2) | 0.11472 (14) | 0.0414 (6) | |
H7A | −0.0110 | 0.4464 | 0.1010 | 0.050* | |
C8A | −0.1898 (4) | 0.3363 (3) | 0.14870 (16) | 0.0518 (7) | |
H8A1 | −0.2888 | 0.3447 | 0.1151 | 0.078* | |
H8A2 | −0.2112 | 0.3864 | 0.1879 | 0.078* | |
H8A3 | −0.1859 | 0.2586 | 0.1650 | 0.078* | |
Br1B | 1.09635 (5) | 0.88973 (3) | 0.153281 (17) | 0.06112 (12) | |
O1B | 0.8026 (3) | 1.13185 (16) | 0.01304 (11) | 0.0500 (5) | |
H1B | 0.8822 | 1.1806 | 0.0214 | 0.075* | |
C1B | 1.1100 (4) | 0.8977 (2) | 0.05449 (14) | 0.0407 (6) | |
C2B | 0.9897 (4) | 0.9647 (2) | 0.01929 (14) | 0.0380 (6) | |
C3B | 1.0055 (5) | 0.9659 (3) | −0.05293 (15) | 0.0493 (7) | |
H3B | 0.9253 | 1.0111 | −0.0796 | 0.059* | |
C4B | 1.1372 (5) | 0.9016 (3) | −0.08555 (18) | 0.0623 (9) | |
H4B | 1.1466 | 0.9031 | −0.1345 | 0.075* | |
C5B | 1.2543 (5) | 0.8358 (3) | −0.0479 (2) | 0.0618 (9) | |
H5B | 1.3445 | 0.7924 | −0.0709 | 0.074* | |
C6B | 1.2412 (4) | 0.8325 (3) | 0.02258 (19) | 0.0525 (8) | |
H6B | 1.3206 | 0.7865 | 0.0490 | 0.063* | |
C7B | 0.8394 (4) | 1.0340 (2) | 0.05289 (14) | 0.0405 (6) | |
H7B | 0.8787 | 1.0565 | 0.1004 | 0.049* | |
C8B | 0.6624 (4) | 0.9675 (3) | 0.05759 (18) | 0.0536 (8) | |
H8B1 | 0.5701 | 1.0119 | 0.0820 | 0.080* | |
H8B2 | 0.6844 | 0.8976 | 0.0828 | 0.080* | |
H8B3 | 0.6186 | 0.9501 | 0.0110 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1A | 0.0939 (3) | 0.04272 (17) | 0.0756 (2) | −0.00522 (18) | 0.0009 (2) | −0.01741 (16) |
O1A | 0.0535 (13) | 0.0491 (11) | 0.0457 (11) | −0.0190 (10) | 0.0097 (9) | −0.0088 (9) |
C1A | 0.0491 (17) | 0.0454 (15) | 0.0431 (15) | −0.0093 (13) | 0.0102 (13) | 0.0011 (13) |
C2A | 0.0390 (14) | 0.0387 (13) | 0.0433 (15) | −0.0040 (12) | 0.0092 (11) | 0.0043 (11) |
C3A | 0.0552 (19) | 0.0476 (18) | 0.063 (2) | 0.0002 (15) | −0.0012 (15) | 0.0025 (14) |
C4A | 0.055 (2) | 0.071 (2) | 0.084 (2) | 0.0115 (18) | 0.0002 (19) | 0.021 (2) |
C5A | 0.0398 (19) | 0.095 (3) | 0.068 (2) | −0.0068 (19) | −0.0046 (16) | 0.023 (2) |
C6A | 0.050 (2) | 0.079 (3) | 0.0525 (18) | −0.0225 (19) | −0.0002 (14) | 0.0029 (16) |
C7A | 0.0470 (16) | 0.0328 (13) | 0.0443 (15) | −0.0035 (12) | 0.0025 (12) | 0.0024 (11) |
C8A | 0.0457 (16) | 0.0612 (19) | 0.0484 (16) | 0.0059 (14) | 0.0041 (14) | 0.0050 (15) |
Br1B | 0.0701 (2) | 0.0615 (2) | 0.05172 (18) | 0.01563 (17) | −0.01687 (16) | 0.00621 (14) |
O1B | 0.0485 (11) | 0.0327 (10) | 0.0688 (13) | −0.0017 (9) | −0.0228 (10) | 0.0000 (9) |
C1B | 0.0397 (14) | 0.0333 (13) | 0.0492 (14) | −0.0042 (12) | −0.0054 (11) | 0.0005 (11) |
C2B | 0.0382 (14) | 0.0275 (12) | 0.0483 (16) | −0.0059 (11) | −0.0018 (12) | −0.0021 (11) |
C3B | 0.0575 (19) | 0.0418 (15) | 0.0484 (17) | −0.0085 (15) | −0.0027 (14) | 0.0026 (12) |
C4B | 0.074 (2) | 0.056 (2) | 0.0568 (18) | −0.0197 (19) | 0.0196 (16) | −0.0120 (15) |
C5B | 0.057 (2) | 0.0431 (17) | 0.085 (3) | −0.0043 (17) | 0.0241 (19) | −0.0118 (17) |
C6B | 0.0377 (16) | 0.0399 (16) | 0.080 (2) | 0.0003 (13) | 0.0012 (15) | −0.0017 (15) |
C7B | 0.0416 (15) | 0.0359 (13) | 0.0440 (15) | 0.0019 (13) | −0.0105 (12) | 0.0015 (11) |
C8B | 0.0430 (17) | 0.0472 (16) | 0.071 (2) | 0.0004 (15) | 0.0005 (15) | 0.0032 (15) |
Br1A—C1A | 1.909 (3) | Br1B—C1B | 1.917 (3) |
O1A—C7A | 1.424 (3) | O1B—C7B | 1.426 (3) |
O1A—H1A | 0.8400 | O1B—H1B | 0.8400 |
C1A—C2A | 1.378 (4) | C1B—C2B | 1.370 (4) |
C1A—C6A | 1.395 (4) | C1B—C6B | 1.383 (4) |
C2A—C3A | 1.391 (4) | C2B—C3B | 1.403 (4) |
C2A—C7A | 1.514 (4) | C2B—C7B | 1.523 (4) |
C3A—C4A | 1.378 (5) | C3B—C4B | 1.385 (5) |
C3A—H3A | 0.9500 | C3B—H3B | 0.9500 |
C4A—C5A | 1.384 (6) | C4B—C5B | 1.373 (5) |
C4A—H4A | 0.9500 | C4B—H4B | 0.9500 |
C5A—C6A | 1.359 (6) | C5B—C6B | 1.369 (5) |
C5A—H5A | 0.9500 | C5B—H5B | 0.9500 |
C6A—H6A | 0.9500 | C6B—H6B | 0.9500 |
C7A—C8A | 1.520 (4) | C7B—C8B | 1.523 (4) |
C7A—H7A | 1.0000 | C7B—H7B | 1.0000 |
C8A—H8A1 | 0.9800 | C8B—H8B1 | 0.9800 |
C8A—H8A2 | 0.9800 | C8B—H8B2 | 0.9800 |
C8A—H8A3 | 0.9800 | C8B—H8B3 | 0.9800 |
C7A—O1A—H1A | 109.5 | C7B—O1B—H1B | 109.5 |
C2A—C1A—C6A | 122.5 (3) | C2B—C1B—C6B | 123.6 (3) |
C2A—C1A—Br1A | 120.5 (2) | C2B—C1B—Br1B | 119.4 (2) |
C6A—C1A—Br1A | 117.0 (2) | C6B—C1B—Br1B | 117.0 (2) |
C1A—C2A—C3A | 116.8 (3) | C1B—C2B—C3B | 116.7 (3) |
C1A—C2A—C7A | 124.2 (3) | C1B—C2B—C7B | 124.7 (3) |
C3A—C2A—C7A | 118.9 (3) | C3B—C2B—C7B | 118.6 (3) |
C4A—C3A—C2A | 121.7 (3) | C4B—C3B—C2B | 120.4 (3) |
C4A—C3A—H3A | 119.2 | C4B—C3B—H3B | 119.8 |
C2A—C3A—H3A | 119.2 | C2B—C3B—H3B | 119.8 |
C3A—C4A—C5A | 119.5 (4) | C5B—C4B—C3B | 120.7 (3) |
C3A—C4A—H4A | 120.3 | C5B—C4B—H4B | 119.6 |
C5A—C4A—H4A | 120.3 | C3B—C4B—H4B | 119.6 |
C6A—C5A—C4A | 120.7 (3) | C6B—C5B—C4B | 120.1 (3) |
C6A—C5A—H5A | 119.6 | C6B—C5B—H5B | 120.0 |
C4A—C5A—H5A | 119.6 | C4B—C5B—H5B | 120.0 |
C5A—C6A—C1A | 118.8 (3) | C5B—C6B—C1B | 118.5 (3) |
C5A—C6A—H6A | 120.6 | C5B—C6B—H6B | 120.7 |
C1A—C6A—H6A | 120.6 | C1B—C6B—H6B | 120.7 |
O1A—C7A—C2A | 111.3 (2) | O1B—C7B—C8B | 107.4 (2) |
O1A—C7A—C8A | 107.9 (2) | O1B—C7B—C2B | 110.6 (2) |
C2A—C7A—C8A | 110.6 (2) | C8B—C7B—C2B | 110.9 (2) |
O1A—C7A—H7A | 109.0 | O1B—C7B—H7B | 109.3 |
C2A—C7A—H7A | 109.0 | C8B—C7B—H7B | 109.3 |
C8A—C7A—H7A | 109.0 | C2B—C7B—H7B | 109.3 |
C7A—C8A—H8A1 | 109.5 | C7B—C8B—H8B1 | 109.5 |
C7A—C8A—H8A2 | 109.5 | C7B—C8B—H8B2 | 109.5 |
H8A1—C8A—H8A2 | 109.5 | H8B1—C8B—H8B2 | 109.5 |
C7A—C8A—H8A3 | 109.5 | C7B—C8B—H8B3 | 109.5 |
H8A1—C8A—H8A3 | 109.5 | H8B1—C8B—H8B3 | 109.5 |
H8A2—C8A—H8A3 | 109.5 | H8B2—C8B—H8B3 | 109.5 |
C6A—C1A—C2A—C3A | −0.4 (4) | C6B—C1B—C2B—C3B | −0.6 (4) |
Br1A—C1A—C2A—C3A | 179.8 (2) | Br1B—C1B—C2B—C3B | −179.3 (2) |
C6A—C1A—C2A—C7A | 177.3 (3) | C6B—C1B—C2B—C7B | 177.6 (3) |
Br1A—C1A—C2A—C7A | −2.5 (4) | Br1B—C1B—C2B—C7B | −1.1 (4) |
C1A—C2A—C3A—C4A | 0.7 (4) | C1B—C2B—C3B—C4B | 0.1 (4) |
C7A—C2A—C3A—C4A | −177.1 (3) | C7B—C2B—C3B—C4B | −178.2 (3) |
C2A—C3A—C4A—C5A | −0.7 (5) | C2B—C3B—C4B—C5B | 0.0 (5) |
C3A—C4A—C5A—C6A | 0.3 (6) | C3B—C4B—C5B—C6B | 0.4 (5) |
C4A—C5A—C6A—C1A | 0.0 (5) | C4B—C5B—C6B—C1B | −0.8 (5) |
C2A—C1A—C6A—C5A | 0.0 (5) | C2B—C1B—C6B—C5B | 1.0 (4) |
Br1A—C1A—C6A—C5A | 179.8 (3) | Br1B—C1B—C6B—C5B | 179.7 (2) |
C1A—C2A—C7A—O1A | 145.5 (3) | C1B—C2B—C7B—O1B | 150.2 (2) |
C3A—C2A—C7A—O1A | −36.9 (3) | C3B—C2B—C7B—O1B | −31.6 (3) |
C1A—C2A—C7A—C8A | −94.5 (3) | C1B—C2B—C7B—C8B | −90.7 (3) |
C3A—C2A—C7A—C8A | 83.1 (3) | C3B—C2B—C7B—C8B | 87.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O1Bi | 0.84 | 1.81 | 2.645 (3) | 177 |
O1B—H1B···O1Aii | 0.84 | 1.81 | 2.627 (3) | 165 |
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C8H9BrO |
Mr | 201.06 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 193 |
a, b, c (Å) | 7.3235 (6), 11.9440 (11), 19.3583 (18) |
V (Å3) | 1693.3 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 4.79 |
Crystal size (mm) | 0.20 × 0.08 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1998) |
Tmin, Tmax | 0.434, 0.680 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12365, 4195, 3420 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.080, 1.03 |
No. of reflections | 4195 |
No. of parameters | 185 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.67, −0.33 |
Absolute structure | Flack, 1983, 1788 Friedel pairs |
Absolute structure parameter | −0.004 (10) |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O1Bi | 0.84 | 1.81 | 2.645 (3) | 176.8 |
O1B—H1B···O1Aii | 0.84 | 1.81 | 2.627 (3) | 165.4 |
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1, y+1, z. |
Footnotes
‡Current address: Michigan State University, Department of Chemistry, East Lansing, MI 48824, USA.
Acknowledgements
The CCD-based X-ray diffractometer at Harvard University was purchased through an NIH grant (1S10RR11937–01).
References
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We have been studying the crystallization properties of enantiomeric compounds and their racemic mixtures, as well as the effect of hydrogen bonding on their crystallization behaviour (Staples and Huang, 2002; Staples and George, 2005). In particular we are interested in those compounds that can act as ligands to transition metal complexes (Staples, 2001). In the course of this study we have structurally characterized the tittle compound, C8H9BrO (I). We have also crystallized the enantiomeric compound, R-(-)-2-bromo-alpha-methyl benzylalcohol, which will be reported later.
S-(+)-2-bromo-alpha-methyl benzylalcohol crystallizes with two molecules in the assymmetric unit and presents intermolecular hydrogen bonding, a fact which can dictate the crystallization as well as solvation properties. It is our hope that we can use this compound for further studies of crystallization and coordination chemistry.
The stucture of S-(+)-2-bromo-alpha-methyl benzylalcohol is shown in Fgure 1. The compound exhibits standard bond lengths and angles, similar to those in closely related compounds (Angiolini et al., 1995; Venkatachalam et al.,2005). It displays hydrogen bonding interactions with neighboring molecules (Table 1), to form a linear type of hydrogen bonding structure (Figure 2). The outcome is a zigzag chain structure containing both unique molecules and evolving around a screw axis along [100].