The molecular structure of the title compound, C
17H
20N
4OS
2, does not show any intramolecular aromatic π–π interactions, but the crystal packing reveals the presence of intermolecular C—H
O and C—H
π interactions. The C—H
O interactions generate chains of molecules that are linked into sheets by C—H
π interactions about inversion centres.
Supporting information
CCDC reference: 221072
Compound (I) was prepared by stirring an equimolar mixture of 4,6-bis- (methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine and 4-phenoxybutyl bromide in DMF/K2CO3 solution. A diffraction-quality crystal was prepared from a solution of (I) in ethyl acetate and methanol by slow evaporation at room temperature.
All H atoms were placed in idealized positions and allowed to ride on their parent atoms for the final cycles of refinement, with C—H distances in the range 0.93–0.97 Å
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
4,6-Bis(methylsulfanyl)-1-(4-phenoxybutyl)-1
H-pyrazolo[3,4-
d]pyrimidine
top
Crystal data top
C17H20N4OS2 | F(000) = 760 |
Mr = 360.49 | Dx = 1.360 Mg m−3 |
Monoclinic, P21/c | Melting point: 355 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 17.966 (1) Å | Cell parameters from 40 reflections |
b = 10.089 (1) Å | θ = 5.0–12.5° |
c = 10.055 (1) Å | µ = 0.31 mm−1 |
β = 104.97 (1)° | T = 293 K |
V = 1760.7 (3) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.023 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 2.3° |
Graphite monochromator | h = −22→21 |
θ–2θ scans | k = −1→12 |
4550 measured reflections | l = −1→12 |
3468 independent reflections | 3 standard reflections every 97 reflections |
2333 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0313P)2 + 0.9524P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3468 reflections | Δρmax = 0.23 e Å−3 |
220 parameters | Δρmin = −0.23 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: 0.0064 (6) |
Crystal data top
C17H20N4OS2 | V = 1760.7 (3) Å3 |
Mr = 360.49 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.966 (1) Å | µ = 0.31 mm−1 |
b = 10.089 (1) Å | T = 293 K |
c = 10.055 (1) Å | 0.30 × 0.25 × 0.20 mm |
β = 104.97 (1)° | |
Data collection top
Bruker P4 diffractometer | Rint = 0.023 |
4550 measured reflections | 3 standard reflections every 97 reflections |
3468 independent reflections | intensity decay: none |
2333 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.23 e Å−3 |
3468 reflections | Δρmin = −0.23 e Å−3 |
220 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. |
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 | Uiso*/Ueq | |
S1 | 0.18353 (4) | −0.04247 (6) | 0.03747 (8) | 0.0517 (2) | |
S2 | 0.02684 (4) | 0.33764 (7) | 0.19747 (8) | 0.0551 (2) | |
N1 | 0.23616 (11) | 0.42670 (19) | −0.0444 (2) | 0.0413 (5) | |
N2 | 0.28677 (12) | 0.3486 (2) | −0.0906 (2) | 0.0488 (5) | |
C3 | 0.27068 (14) | 0.2253 (3) | −0.0649 (3) | 0.0487 (6) | |
H3 | 0.2961 | 0.1515 | −0.0870 | 0.058* | |
C3A | 0.20969 (13) | 0.2193 (2) | 0.0005 (2) | 0.0397 (5) | |
C4 | 0.16530 (13) | 0.1266 (2) | 0.0511 (2) | 0.0407 (6) | |
N5 | 0.11045 (11) | 0.16672 (19) | 0.1088 (2) | 0.0424 (5) | |
C6 | 0.09928 (13) | 0.3001 (2) | 0.1153 (2) | 0.0413 (6) | |
N7 | 0.13496 (11) | 0.39740 (19) | 0.0698 (2) | 0.0418 (5) | |
C7A | 0.18985 (12) | 0.3516 (2) | 0.0124 (2) | 0.0381 (5) | |
C8 | 0.24105 (14) | 0.5703 (2) | −0.0463 (2) | 0.0452 (6) | |
H8A | 0.1925 | 0.6073 | −0.0386 | 0.054* | |
H8B | 0.2489 | 0.5982 | −0.1340 | 0.054* | |
C9 | 0.30577 (14) | 0.6254 (2) | 0.0689 (2) | 0.0425 (6) | |
H9A | 0.3548 | 0.5977 | 0.0543 | 0.051* | |
H9B | 0.3039 | 0.7215 | 0.0652 | 0.051* | |
C10 | 0.30141 (14) | 0.5804 (3) | 0.2106 (2) | 0.0453 (6) | |
H10A | 0.2537 | 0.6122 | 0.2273 | 0.054* | |
H10B | 0.3006 | 0.4843 | 0.2130 | 0.054* | |
C11 | 0.36802 (14) | 0.6299 (2) | 0.3234 (2) | 0.0416 (6) | |
H11A | 0.4165 | 0.6060 | 0.3041 | 0.050* | |
H11B | 0.3658 | 0.7255 | 0.3309 | 0.050* | |
O12 | 0.36153 (9) | 0.56835 (16) | 0.44844 (16) | 0.0448 (4) | |
C13 | 0.41914 (13) | 0.5879 (2) | 0.5664 (2) | 0.0377 (5) | |
C14 | 0.40921 (15) | 0.5258 (3) | 0.6833 (2) | 0.0465 (6) | |
H14 | 0.3657 | 0.4742 | 0.6786 | 0.056* | |
C15 | 0.46360 (15) | 0.5406 (3) | 0.8062 (3) | 0.0528 (7) | |
H15 | 0.4566 | 0.4991 | 0.8847 | 0.063* | |
C16 | 0.52859 (15) | 0.6165 (3) | 0.8148 (3) | 0.0532 (7) | |
H16 | 0.5654 | 0.6258 | 0.8984 | 0.064* | |
C17 | 0.53846 (14) | 0.6782 (3) | 0.6983 (3) | 0.0512 (7) | |
H17 | 0.5820 | 0.7298 | 0.7036 | 0.061* | |
C18 | 0.48385 (14) | 0.6642 (2) | 0.5731 (3) | 0.0454 (6) | |
H18 | 0.4908 | 0.7057 | 0.4946 | 0.055* | |
C19 | 0.10826 (16) | −0.1177 (3) | 0.0982 (3) | 0.0617 (8) | |
H19A | 0.1109 | −0.0868 | 0.1896 | 0.092* | |
H19B | 0.1143 | −0.2123 | 0.0994 | 0.092* | |
H19C | 0.0592 | −0.0944 | 0.0382 | 0.092* | |
C20 | 0.02897 (16) | 0.5155 (3) | 0.2001 (3) | 0.0575 (7) | |
H20A | 0.0792 | 0.5452 | 0.2500 | 0.086* | |
H20B | −0.0089 | 0.5480 | 0.2441 | 0.086* | |
H20C | 0.0177 | 0.5484 | 0.1074 | 0.086* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0517 (4) | 0.0389 (3) | 0.0685 (5) | 0.0015 (3) | 0.0229 (3) | −0.0055 (3) |
S2 | 0.0544 (4) | 0.0478 (4) | 0.0733 (5) | 0.0022 (3) | 0.0351 (4) | −0.0039 (4) |
N1 | 0.0427 (11) | 0.0436 (12) | 0.0390 (11) | −0.0036 (9) | 0.0131 (9) | −0.0026 (9) |
N2 | 0.0500 (12) | 0.0540 (13) | 0.0479 (12) | −0.0016 (10) | 0.0227 (10) | −0.0071 (11) |
C3 | 0.0495 (15) | 0.0474 (14) | 0.0537 (16) | −0.0005 (12) | 0.0218 (13) | −0.0092 (13) |
C3A | 0.0384 (12) | 0.0417 (13) | 0.0400 (13) | −0.0021 (11) | 0.0119 (11) | −0.0050 (11) |
C4 | 0.0397 (13) | 0.0397 (13) | 0.0398 (14) | 0.0002 (10) | 0.0053 (11) | −0.0061 (11) |
N5 | 0.0418 (11) | 0.0393 (11) | 0.0488 (12) | 0.0011 (9) | 0.0165 (9) | −0.0021 (10) |
C6 | 0.0381 (12) | 0.0429 (14) | 0.0434 (14) | 0.0004 (10) | 0.0114 (11) | −0.0045 (11) |
N7 | 0.0425 (11) | 0.0387 (11) | 0.0462 (12) | 0.0026 (9) | 0.0150 (10) | −0.0023 (9) |
C7A | 0.0356 (12) | 0.0423 (13) | 0.0358 (13) | −0.0019 (10) | 0.0082 (10) | −0.0019 (11) |
C8 | 0.0519 (14) | 0.0441 (14) | 0.0391 (14) | −0.0020 (12) | 0.0107 (12) | 0.0075 (12) |
C9 | 0.0480 (14) | 0.0378 (13) | 0.0432 (14) | −0.0038 (11) | 0.0141 (12) | 0.0039 (11) |
C10 | 0.0481 (14) | 0.0489 (14) | 0.0406 (14) | −0.0078 (12) | 0.0144 (11) | 0.0011 (12) |
C11 | 0.0492 (14) | 0.0405 (13) | 0.0363 (13) | −0.0044 (11) | 0.0135 (11) | 0.0005 (11) |
O12 | 0.0496 (10) | 0.0497 (10) | 0.0355 (9) | −0.0091 (8) | 0.0117 (8) | 0.0024 (8) |
C13 | 0.0457 (13) | 0.0334 (12) | 0.0345 (13) | 0.0034 (10) | 0.0110 (11) | −0.0039 (10) |
C14 | 0.0516 (14) | 0.0467 (14) | 0.0430 (15) | 0.0003 (12) | 0.0156 (12) | 0.0014 (12) |
C15 | 0.0636 (17) | 0.0567 (16) | 0.0376 (15) | 0.0113 (14) | 0.0121 (13) | 0.0033 (13) |
C16 | 0.0536 (16) | 0.0547 (16) | 0.0459 (16) | 0.0130 (13) | 0.0030 (13) | −0.0091 (13) |
C17 | 0.0436 (14) | 0.0467 (15) | 0.0610 (18) | −0.0004 (12) | 0.0094 (13) | −0.0088 (14) |
C18 | 0.0520 (14) | 0.0405 (13) | 0.0455 (15) | 0.0000 (11) | 0.0158 (12) | 0.0018 (12) |
C19 | 0.0597 (17) | 0.0469 (16) | 0.082 (2) | −0.0051 (13) | 0.0243 (16) | −0.0007 (15) |
C20 | 0.0622 (17) | 0.0491 (16) | 0.0660 (19) | 0.0066 (13) | 0.0254 (15) | −0.0088 (14) |
Geometric parameters (Å, º) top
S1—C4 | 1.749 (2) | C10—H10A | 0.9700 |
S1—C19 | 1.790 (3) | C10—H10B | 0.9700 |
S2—C6 | 1.754 (2) | C11—O12 | 1.434 (3) |
S2—C20 | 1.794 (3) | C11—H11A | 0.9700 |
N1—C7A | 1.356 (3) | C11—H11B | 0.9700 |
N1—N2 | 1.371 (3) | O12—C13 | 1.372 (3) |
N1—C8 | 1.452 (3) | C13—C18 | 1.381 (3) |
N2—C3 | 1.318 (3) | C13—C14 | 1.383 (3) |
C3—C3A | 1.418 (3) | C14—C15 | 1.371 (3) |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C3A—C7A | 1.394 (3) | C15—C16 | 1.380 (4) |
C3A—C4 | 1.407 (3) | C15—H15 | 0.9300 |
C4—N5 | 1.329 (3) | C16—C17 | 1.378 (4) |
N5—C6 | 1.365 (3) | C16—H16 | 0.9300 |
C6—N7 | 1.317 (3) | C17—C18 | 1.389 (3) |
N7—C7A | 1.346 (3) | C17—H17 | 0.9300 |
C8—C9 | 1.519 (3) | C18—H18 | 0.9300 |
C8—H8A | 0.9700 | C19—H19A | 0.9600 |
C8—H8B | 0.9700 | C19—H19B | 0.9600 |
C9—C10 | 1.517 (3) | C19—H19C | 0.9600 |
C9—H9A | 0.9700 | C20—H20A | 0.9600 |
C9—H9B | 0.9700 | C20—H20B | 0.9600 |
C10—C11 | 1.505 (3) | C20—H20C | 0.9600 |
| | | |
C6—S2—C20 | 101.95 (12) | C9—C10—H10B | 109.1 |
C4—S1—C19 | 102.34 (12) | H10A—C10—H10B | 107.8 |
C7A—N1—N2 | 110.74 (19) | O12—C11—C10 | 106.77 (18) |
C7A—N1—C8 | 127.5 (2) | O12—C11—H11A | 110.4 |
N2—N1—C8 | 121.41 (19) | C10—C11—H11A | 110.4 |
C3—N2—N1 | 106.15 (19) | O12—C11—H11B | 110.4 |
N2—C3—C3A | 111.4 (2) | C10—C11—H11B | 110.4 |
N2—C3—H3 | 124.3 | H11A—C11—H11B | 108.6 |
C3A—C3—H3 | 124.3 | C13—O12—C11 | 118.82 (18) |
C7A—C3A—C4 | 115.1 (2) | O12—C13—C18 | 124.0 (2) |
C7A—C3A—C3 | 104.2 (2) | O12—C13—C14 | 115.8 (2) |
C4—C3A—C3 | 140.7 (2) | C18—C13—C14 | 120.1 (2) |
N5—C4—C3A | 120.6 (2) | C15—C14—C13 | 119.9 (2) |
N5—C4—S1 | 120.41 (18) | C15—C14—H14 | 120.0 |
C3A—C4—S1 | 119.02 (18) | C13—C14—H14 | 120.0 |
C4—N5—C6 | 117.1 (2) | C14—C15—C16 | 120.7 (3) |
N7—C6—N5 | 128.8 (2) | C14—C15—H15 | 119.6 |
N7—C6—S2 | 119.34 (18) | C16—C15—H15 | 119.6 |
N5—C6—S2 | 111.81 (17) | C17—C16—C15 | 119.3 (2) |
C6—N7—C7A | 111.7 (2) | C17—C16—H16 | 120.3 |
N7—C7A—N1 | 125.8 (2) | C15—C16—H16 | 120.3 |
N7—C7A—C3A | 126.7 (2) | C16—C17—C18 | 120.5 (2) |
N1—C7A—C3A | 107.48 (19) | C16—C17—H17 | 119.7 |
N1—C8—C9 | 113.1 (2) | C18—C17—H17 | 119.7 |
N1—C8—H8A | 109.0 | C13—C18—C17 | 119.3 (2) |
C9—C8—H8A | 109.0 | C13—C18—H18 | 120.3 |
N1—C8—H8B | 109.0 | C17—C18—H18 | 120.3 |
C9—C8—H8B | 109.0 | S1—C19—H19A | 109.5 |
H8A—C8—H8B | 107.8 | S1—C19—H19B | 109.5 |
C10—C9—C8 | 113.05 (19) | H19A—C19—H19B | 109.5 |
C10—C9—H9A | 109.0 | S1—C19—H19C | 109.5 |
C8—C9—H9A | 109.0 | H19A—C19—H19C | 109.5 |
C10—C9—H9B | 109.0 | H19B—C19—H19C | 109.5 |
C8—C9—H9B | 109.0 | S2—C20—H20A | 109.5 |
H9A—C9—H9B | 107.8 | S2—C20—H20B | 109.5 |
C11—C10—C9 | 112.62 (19) | H20A—C20—H20B | 109.5 |
C11—C10—H10A | 109.1 | S2—C20—H20C | 109.5 |
C9—C10—H10A | 109.1 | H20A—C20—H20C | 109.5 |
C11—C10—H10B | 109.1 | H20B—C20—H20C | 109.5 |
| | | |
C7A—N1—N2—C3 | 1.3 (3) | N2—N1—C7A—C3A | −1.3 (3) |
C8—N1—N2—C3 | 175.2 (2) | C8—N1—C7A—C3A | −174.7 (2) |
N1—N2—C3—C3A | −0.8 (3) | C4—C3A—C7A—N7 | 1.9 (4) |
N2—C3—C3A—C7A | 0.1 (3) | C3—C3A—C7A—N7 | −179.2 (2) |
N2—C3—C3A—C4 | 178.5 (3) | C4—C3A—C7A—N1 | −178.17 (19) |
C7A—C3A—C4—N5 | −1.8 (3) | C3—C3A—C7A—N1 | 0.7 (3) |
C3—C3A—C4—N5 | 179.9 (3) | C7A—N1—C8—C9 | 96.0 (3) |
C7A—C3A—C4—S1 | 178.39 (17) | N2—N1—C8—C9 | −76.7 (3) |
C3—C3A—C4—S1 | 0.1 (4) | N1—C8—C9—C10 | −55.2 (3) |
C19—S1—C4—N5 | 5.7 (2) | C8—C9—C10—C11 | 177.0 (2) |
C19—S1—C4—C3A | −174.5 (2) | C9—C10—C11—O12 | −173.54 (19) |
C3A—C4—N5—C6 | 0.5 (3) | C10—C11—O12—C13 | 174.57 (19) |
S1—C4—N5—C6 | −179.72 (17) | C11—O12—C13—C18 | 0.2 (3) |
C4—N5—C6—N7 | 1.2 (4) | C11—O12—C13—C14 | 179.9 (2) |
C4—N5—C6—S2 | −178.59 (16) | O12—C13—C14—C15 | −179.5 (2) |
C20—S2—C6—N7 | −3.1 (2) | C18—C13—C14—C15 | 0.3 (4) |
C20—S2—C6—N5 | 176.73 (19) | C13—C14—C15—C16 | −0.3 (4) |
N5—C6—N7—C7A | −1.1 (4) | C14—C15—C16—C17 | 0.3 (4) |
S2—C6—N7—C7A | 178.60 (17) | C15—C16—C17—C18 | −0.3 (4) |
C6—N7—C7A—N1 | 179.6 (2) | O12—C13—C18—C17 | 179.5 (2) |
C6—N7—C7A—C3A | −0.5 (3) | C14—C13—C18—C17 | −0.3 (3) |
N2—N1—C7A—N7 | 178.6 (2) | C16—C17—C18—C13 | 0.3 (4) |
C8—N1—C7A—N7 | 5.3 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O12i | 0.93 | 2.49 | 3.368 (3) | 157 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Experimental details
Crystal data |
Chemical formula | C17H20N4OS2 |
Mr | 360.49 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 17.966 (1), 10.089 (1), 10.055 (1) |
β (°) | 104.97 (1) |
V (Å3) | 1760.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
|
Data collection |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4550, 3468, 2333 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.105, 1.05 |
No. of reflections | 3468 |
No. of parameters | 220 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.23 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O12i | 0.93 | 2.49 | 3.368 (3) | 157 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Arene interactions are known to play an important role in chemistry (Hunter & Sanders, 1990; Hunter et al., 2001; Tsuzuki et al., 2002) and biology. These interactions play a significant role in molecular recognition, stabilization of DNA/RNA structures (Hobza & Sponer, 1999), crystal engineering (Desiraju, 1995) and drug development (Meyer et al., 2003). Use of a polymethylene, especially a trimethylene (propylene), linker for studying intramolecular π–π interactions was pioneered by Browne et al. (1968), and early work has been reviewed by Leonard (1979). In 1995 we reported the synthesis (Avasthi et al., 1995) and X-ray structure (Biswas et al., 1995) of a `trimethylene linker' molecule that exhibits intramolecular stacking based on a pyrazolo[3,4-d]pyrimidine core, which is isomeric with the biologically important purine system. The robustness of the unusual U-motif formed as a result of the intramolecular stacking has been further demonstrated by X-ray diffraction of other closely related "propylene linker" compounds (Maulik et al., 1998; Avasthi, Aswal & Maulik, 2001; Avasthi, Rawat et al., 2001). Interestingly, no intramolecular stacking is observed by X-ray diffraction when the `trimethylene linker' is replaced by an `ethylene linker' (Avasthi, Rawat et al., 2001), a `tetramethylene linker' (Maulik et al., 2000) or a `pentamethylene linker' (Avasthi et al., 2003). All of these compounds have pyrazolo[3,4-d]pyrimidine-derived moieties at both ends of the polymethylene linker.
We report here the structure of the dissymmetric title compound, (I) (Fig. 1), which has normal dimensions and which has the same pyrazolo[3,4-d]pyrimidine core as reported in previous work on a `propylene linker' dissymmetric compound, (II) (Avasthi et al., 2002). Compound (I) has a `tetramethylene linker' flanked by pyrazolo[3,4-d]pyrimidinyl and electron-rich phenoxy moieties. It was anticipated that this configuration might have facilitated intramolecular stacking between the electron-rich phenoxy moiety and the electron-deficient pyrimidine portion, but Fig. 1 and various geometry calculations do not show any intramolecular stacking between the pyrazolo[3,4-d]pyrimidinyl and phenoxy moieties.
In the crystal structure, the molecules are linked by C—H···O hydrogen bonds (Table 2 and Fig. 2a) and chains of molecules are developed in the c direction by the operation of a c-glide plane. There are also C—H···π interactions between inversion-related molecules, as shown in Fig. 2(b), between C11—H11A and the centroid of the C13–C18 phenyl ring at (1 − x,1 − y,1 − z) [H11···Cg = 2.87 and C11—H11A···Cg = 146°; Cg is the centroid of the C13–C18 phenyl ring at (1 − x,1 − y,1 − z)]. These interactions link the chains of molecules into sheets.