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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1811.
Published online 2009 July 11. doi:  10.1107/S1600536809024738
PMCID: PMC2977094

Methyl 1-methyl-3-p-tolyl-1,2,3,3a,4,11c-hexa­hydro­benzo[f]chromeno[4,3-b]pyrrole-3a-carboxyl­ate

Abstract

In the title compound, C25H25NO3, the dihydro­pyran ring adopts a half-chair conformation, whereas the pyrrolidine ring is in a twist conformation. The tolyl group is oriented at an angle of 82.92 (7)° with respect to the napthalene ring system. In the crystal structure, mol­ecules are linked into centrosymmetric dimers by C—H(...)π inter­actions involving the benzene ring of the tolyl group.

Related literature

For the biological activity of pyrrole derivatives, see: Biava et al. (2005 [triangle]); Borthwick et al. (2000 [triangle]); Caine (1993 [triangle]); Carlson (1993 [triangle]); Fernandes et al. (2004 [triangle]); Jiang et al. (2004 [triangle]); Sokoloff et al. (1990 [triangle]); Tidey & Miczek (1992 [triangle]); Wilner (1985 [triangle]). For a related structure, see: Gunasekaran et al. (2009 [triangle]). For ring-puckering parameters, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1811-scheme1.jpg

Experimental

Crystal data

  • C25H25NO3
  • M r = 387.46
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1811-efi1.jpg
  • a = 12.9899 (6) Å
  • b = 7.6751 (3) Å
  • c = 20.5073 (9) Å
  • β = 96.881 (2)°
  • V = 2029.83 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.25 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa-APEXII area-detector diffractometer
  • Absorption correction: multi-scan (Blessing, 1995 [triangle]) T min = 0.980, T max = 0.984
  • 22975 measured reflections
  • 4790 independent reflections
  • 3176 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.156
  • S = 1.05
  • 4790 reflections
  • 265 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024738/ci2823sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024738/ci2823Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

SN thanks Dr. Babu Vargheese, SAIF, IIT Madras, India, for his help with the data collection. SN thanks SRM management, India, for their support.

supplementary crystallographic information

Comment

Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993), aggressiveness (Tidey & Miczek, 1992), parkinson's disease (Carlson, 1993), psychoses, memory disorders (Sokoloff et al., 1990), anxiety and depression (Wilner, 1985). Pyrrole derivatives have good in vitro activities against mycobacteria and candidae (Biava et al., 2005). These derivatives also possess anti-inflammatory (Fernandes et al., 2004) and antiviral (Borthwick et al., 2000) activities. It has also been shown that N–substituted pyrrole derivatives inhibit human immuno deficiency virus type-I (HIV-I) (Jiang et al., 2004). In view of its medicinal importance, the crystal structure determination of the title compound was undertaken.

The geometric parameters of the title molecule (Fig. 1) agree well with those reported for a similar structure (Gunasekaran et al., 2009). The sum of bond angles around atom N1 (334.0°) is in accordance with sp3 hybridization. The napthalene ring system (C2-C11) and the tolyl group (C16-C22) are oriented at an angle of 82.92 (7)° with respect to each other. The heterocyclic ring (O1/C1/C2/C11-C13) of the chromenopyrrole unit adopts a half-chair conformation, with puckering parameters Q = 0.462 (2) Å, θ = 49.3 (2)° and [var phi]= 261.2 (2)° (Cremer and Pople, 1975). The pyrrolidine ring (N1/C1/C13-C15) adopts a twist conformation, with puckering parameters of q2 = 0.485 (1) Å and [var phi] = 16.2 (2)° (Cremer and Pople, 1975).

The crystal packing is stabilized by weak intermolecular C—H···π [C22—H22A···Cg1; Cg1 is the centroid of the C16—C21 ring] interactions (Table 1).

Experimental

A mixture of (Z)-methyl 2-((1-formylnaphthalen-2-yloxy)methyl)-3- p-tolylacrylate (20 mmol) and sarcosine (30 mmol) was refluxed in benzene for 20 h and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. A chloroform and methanol (1:1) solvent mixture was used for the crystallization under slow evaporation method.

Refinement

H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C-H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H respectively, and Uiso(H) = 1.5Ueq(C) for methyl H and Uiso(H) = 1.2Ueq(C) for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, with 30% probability displacement ellipsoids.
Fig. 2.
The packing of the molecules viewed down the a axis. H atoms not involed in C—H···π interactions (dashed lines) have been omitted.

Crystal data

C25H25NO3F(000) = 824
Mr = 387.46Dx = 1.268 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6463 reflections
a = 12.9899 (6) Åθ = 2.8–25.6°
b = 7.6751 (3) ŵ = 0.08 mm1
c = 20.5073 (9) ÅT = 293 K
β = 96.881 (2)°Prism, colourless
V = 2029.83 (15) Å30.25 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker Kappa-APEXII area-detector diffractometer4790 independent reflections
Radiation source: fine-focus sealed tube3176 reflections with I > 2σ(I)
graphiteRint = 0.028
ω and [var phi] scansθmax = 27.8°, θmin = 1.8°
Absorption correction: multi-scan (Blessing, 1995)h = −17→16
Tmin = 0.980, Tmax = 0.984k = −8→10
22975 measured reflectionsl = −20→26

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.081P)2 + 0.2107P] where P = (Fo2 + 2Fc2)/3
4790 reflections(Δ/σ)max = 0.001
265 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.19 e Å3

Special details

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)

xyzUiso*/Ueq
C1−0.09259 (11)0.31953 (19)0.17432 (7)0.0388 (3)
H1−0.07900.21920.14710.047*
C2−0.08470 (10)0.48434 (19)0.13573 (7)0.0384 (3)
C3−0.11550 (11)0.4919 (2)0.06634 (7)0.0446 (4)
C4−0.15523 (13)0.3466 (3)0.02933 (8)0.0558 (4)
H4−0.16210.24060.05030.067*
C5−0.18383 (15)0.3592 (3)−0.03703 (9)0.0697 (6)
H5−0.21040.2622−0.06050.084*
C6−0.17327 (16)0.5168 (4)−0.06962 (10)0.0765 (6)
H6−0.19290.5245−0.11470.092*
C7−0.13492 (15)0.6571 (3)−0.03608 (9)0.0681 (6)
H7−0.12830.7612−0.05840.082*
C8−0.10438 (12)0.6502 (2)0.03225 (8)0.0527 (4)
C9−0.06138 (14)0.7959 (2)0.06742 (9)0.0569 (5)
H9−0.05510.90070.04540.068*
C10−0.02925 (12)0.7865 (2)0.13232 (9)0.0499 (4)
H10−0.00010.88350.15460.060*
C11−0.04003 (11)0.6293 (2)0.16629 (7)0.0412 (4)
C12−0.02357 (12)0.4915 (2)0.27124 (7)0.0421 (4)
H12A−0.09310.50770.28300.051*
H12B0.02410.49230.31150.051*
C13−0.01754 (11)0.31594 (19)0.23809 (7)0.0383 (3)
C14−0.06451 (12)0.1678 (2)0.27941 (8)0.0460 (4)
H14−0.02390.06160.27520.055*
C15−0.17243 (13)0.1390 (2)0.24138 (8)0.0541 (4)
H15A−0.17320.03530.21430.065*
H15B−0.22450.12680.27130.065*
C16−0.06274 (12)0.2062 (2)0.35187 (8)0.0452 (4)
C170.02402 (13)0.1666 (2)0.39539 (9)0.0560 (5)
H170.08150.11760.37940.067*
C180.02723 (15)0.1980 (3)0.46167 (10)0.0649 (5)
H180.08670.16910.48950.078*
C19−0.05580 (15)0.2713 (2)0.48788 (8)0.0584 (5)
C20−0.14203 (14)0.3124 (2)0.44449 (9)0.0579 (5)
H20−0.19910.36310.46040.070*
C21−0.14554 (13)0.2801 (2)0.37841 (9)0.0537 (4)
H21−0.20520.30860.35070.064*
C22−0.0533 (2)0.3059 (3)0.56044 (9)0.0838 (7)
H22A−0.01960.41540.57110.126*
H22B−0.01570.21440.58480.126*
H22C−0.12290.31000.57170.126*
C23−0.28437 (12)0.2833 (2)0.15488 (9)0.0548 (4)
H23A−0.28140.18130.12810.082*
H23B−0.28970.38500.12750.082*
H23C−0.34380.27630.17840.082*
C240.09063 (12)0.2649 (2)0.22557 (8)0.0416 (4)
C250.26911 (14)0.2845 (3)0.26242 (13)0.0781 (6)
H25A0.27730.16270.27230.117*
H25B0.31560.35070.29290.117*
H25C0.28470.30570.21850.117*
N1−0.19140 (9)0.29402 (17)0.20102 (6)0.0447 (3)
O10.00093 (8)0.63413 (14)0.23080 (5)0.0468 (3)
O20.16331 (8)0.33635 (16)0.26780 (7)0.0646 (4)
O30.10931 (9)0.16459 (17)0.18379 (6)0.0630 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0344 (7)0.0380 (8)0.0430 (8)−0.0011 (6)0.0001 (6)−0.0058 (7)
C20.0304 (7)0.0415 (8)0.0431 (8)0.0015 (6)0.0038 (6)0.0003 (7)
C30.0321 (7)0.0576 (10)0.0441 (8)0.0046 (7)0.0051 (6)−0.0006 (8)
C40.0458 (9)0.0734 (12)0.0471 (9)−0.0008 (8)0.0007 (7)−0.0069 (9)
C50.0537 (11)0.1041 (17)0.0497 (10)−0.0019 (10)−0.0004 (8)−0.0152 (12)
C60.0628 (12)0.123 (2)0.0424 (10)0.0045 (12)0.0015 (9)0.0075 (13)
C70.0589 (11)0.0952 (16)0.0508 (11)0.0062 (11)0.0099 (9)0.0179 (11)
C80.0393 (8)0.0695 (12)0.0498 (9)0.0082 (8)0.0079 (7)0.0100 (9)
C90.0514 (10)0.0550 (10)0.0657 (12)0.0057 (8)0.0125 (9)0.0172 (9)
C100.0451 (9)0.0411 (9)0.0641 (11)0.0012 (7)0.0087 (8)0.0018 (8)
C110.0346 (7)0.0417 (8)0.0475 (9)0.0029 (6)0.0060 (6)0.0003 (7)
C120.0416 (8)0.0425 (8)0.0412 (8)−0.0030 (6)0.0009 (6)−0.0026 (7)
C130.0356 (7)0.0374 (8)0.0405 (8)−0.0027 (6)−0.0004 (6)−0.0008 (7)
C140.0456 (9)0.0403 (8)0.0514 (9)−0.0048 (6)0.0026 (7)0.0029 (7)
C150.0522 (10)0.0549 (10)0.0532 (10)−0.0157 (8)−0.0020 (8)0.0042 (8)
C160.0408 (8)0.0444 (9)0.0492 (9)−0.0051 (7)0.0006 (7)0.0091 (7)
C170.0427 (9)0.0659 (11)0.0578 (11)0.0057 (8)0.0004 (8)0.0116 (9)
C180.0535 (11)0.0802 (13)0.0570 (11)−0.0022 (9)−0.0100 (8)0.0153 (10)
C190.0630 (11)0.0621 (11)0.0489 (10)−0.0158 (9)0.0020 (9)0.0107 (9)
C200.0515 (10)0.0659 (11)0.0578 (11)−0.0034 (8)0.0123 (8)0.0048 (9)
C210.0420 (9)0.0638 (11)0.0535 (10)0.0009 (8)−0.0013 (7)0.0090 (9)
C220.1037 (18)0.0954 (17)0.0512 (11)−0.0230 (14)0.0053 (11)0.0049 (11)
C230.0395 (9)0.0615 (11)0.0613 (10)−0.0084 (7)−0.0022 (8)−0.0030 (9)
C240.0399 (8)0.0368 (8)0.0468 (9)−0.0003 (6)−0.0005 (7)0.0044 (7)
C250.0356 (10)0.0670 (13)0.1270 (19)0.0046 (8)−0.0098 (10)−0.0069 (12)
N10.0348 (7)0.0491 (8)0.0489 (7)−0.0082 (5)−0.0005 (5)−0.0006 (6)
O10.0517 (6)0.0394 (6)0.0475 (6)−0.0069 (5)−0.0009 (5)−0.0037 (5)
O20.0366 (6)0.0623 (8)0.0905 (9)0.0003 (5)−0.0102 (6)−0.0199 (7)
O30.0515 (7)0.0710 (8)0.0657 (8)0.0128 (6)0.0039 (6)−0.0153 (7)

Geometric parameters (Å, °)

C1—N11.4676 (18)C14—C151.536 (2)
C1—C21.502 (2)C14—H140.98
C1—C131.5348 (19)C15—N11.454 (2)
C1—H10.98C15—H15A0.97
C2—C111.371 (2)C15—H15B0.97
C2—C31.432 (2)C16—C211.384 (2)
C3—C41.411 (2)C16—C171.385 (2)
C3—C81.418 (2)C17—C181.376 (3)
C4—C51.370 (2)C17—H170.93
C4—H40.93C18—C191.381 (3)
C5—C61.397 (3)C18—H180.93
C5—H50.93C19—C201.381 (3)
C6—C71.341 (3)C19—C221.508 (3)
C6—H60.93C20—C211.373 (2)
C7—C81.411 (3)C20—H200.93
C7—H70.93C21—H210.93
C8—C91.409 (3)C22—H22A0.96
C9—C101.348 (2)C22—H22B0.96
C9—H90.93C22—H22C0.96
C10—C111.409 (2)C23—N11.4445 (19)
C10—H100.93C23—H23A0.96
C11—O11.3661 (18)C23—H23B0.96
C12—O11.4318 (18)C23—H23C0.96
C12—C131.516 (2)C24—O31.1983 (19)
C12—H12A0.97C24—O21.3214 (19)
C12—H12B0.97C25—O21.448 (2)
C13—C241.510 (2)C25—H25A0.96
C13—C141.583 (2)C25—H25B0.96
C14—C161.512 (2)C25—H25C0.96
N1—C1—C2115.26 (12)C15—C14—H14107.7
N1—C1—C13100.04 (11)C13—C14—H14107.7
C2—C1—C13112.81 (12)N1—C15—C14104.68 (12)
N1—C1—H1109.4N1—C15—H15A110.8
C2—C1—H1109.4C14—C15—H15A110.8
C13—C1—H1109.4N1—C15—H15B110.8
C11—C2—C3118.29 (14)C14—C15—H15B110.8
C11—C2—C1119.61 (13)H15A—C15—H15B108.9
C3—C2—C1121.93 (13)C21—C16—C17116.58 (15)
C4—C3—C8117.66 (15)C21—C16—C14123.05 (14)
C4—C3—C2122.89 (15)C17—C16—C14120.37 (15)
C8—C3—C2119.44 (15)C18—C17—C16121.60 (17)
C5—C4—C3121.10 (19)C18—C17—H17119.2
C5—C4—H4119.5C16—C17—H17119.2
C3—C4—H4119.5C17—C18—C19121.54 (17)
C4—C5—C6120.4 (2)C17—C18—H18119.2
C4—C5—H5119.8C19—C18—H18119.2
C6—C5—H5119.8C20—C19—C18116.95 (17)
C7—C6—C5120.10 (18)C20—C19—C22121.04 (19)
C7—C6—H6119.9C18—C19—C22122.01 (19)
C5—C6—H6119.9C21—C20—C19121.54 (17)
C6—C7—C8121.5 (2)C21—C20—H20119.2
C6—C7—H7119.2C19—C20—H20119.2
C8—C7—H7119.2C20—C21—C16121.79 (16)
C9—C8—C7121.71 (18)C20—C21—H21119.1
C9—C8—C3119.04 (15)C16—C21—H21119.1
C7—C8—C3119.24 (18)C19—C22—H22A109.5
C10—C9—C8121.28 (16)C19—C22—H22B109.5
C10—C9—H9119.4H22A—C22—H22B109.5
C8—C9—H9119.4C19—C22—H22C109.5
C9—C10—C11119.79 (16)H22A—C22—H22C109.5
C9—C10—H10120.1H22B—C22—H22C109.5
C11—C10—H10120.1N1—C23—H23A109.5
O1—C11—C2124.01 (13)N1—C23—H23B109.5
O1—C11—C10113.90 (13)H23A—C23—H23B109.5
C2—C11—C10122.05 (14)N1—C23—H23C109.5
O1—C12—C13113.13 (11)H23A—C23—H23C109.5
O1—C12—H12A109.0H23B—C23—H23C109.5
C13—C12—H12A109.0O3—C24—O2123.05 (15)
O1—C12—H12B109.0O3—C24—C13124.09 (14)
C13—C12—H12B109.0O2—C24—C13112.79 (14)
H12A—C12—H12B107.8O2—C25—H25A109.5
C24—C13—C12113.95 (12)O2—C25—H25B109.5
C24—C13—C1111.64 (12)H25A—C25—H25B109.5
C12—C13—C1107.73 (12)O2—C25—H25C109.5
C24—C13—C14109.32 (12)H25A—C25—H25C109.5
C12—C13—C14110.77 (12)H25B—C25—H25C109.5
C1—C13—C14102.87 (11)C23—N1—C15113.43 (13)
C16—C14—C15115.62 (14)C23—N1—C1117.60 (13)
C16—C14—C13115.10 (12)C15—N1—C1103.03 (12)
C15—C14—C13102.60 (12)C11—O1—C12116.89 (11)
C16—C14—H14107.7C24—O2—C25116.50 (15)
N1—C1—C2—C1194.97 (15)C12—C13—C14—C16−24.73 (17)
C13—C1—C2—C11−19.09 (18)C1—C13—C14—C16−139.61 (13)
N1—C1—C2—C3−89.82 (16)C24—C13—C14—C15−131.92 (14)
C13—C1—C2—C3156.12 (13)C12—C13—C14—C15101.71 (14)
C11—C2—C3—C4175.31 (14)C1—C13—C14—C15−13.17 (15)
C1—C2—C3—C40.0 (2)C16—C14—C15—N1108.16 (15)
C11—C2—C3—C8−3.5 (2)C13—C14—C15—N1−17.95 (16)
C1—C2—C3—C8−178.76 (13)C15—C14—C16—C21−25.5 (2)
C8—C3—C4—C5−1.2 (2)C13—C14—C16—C2193.96 (18)
C2—C3—C4—C5180.00 (15)C15—C14—C16—C17154.05 (15)
C3—C4—C5—C60.6 (3)C13—C14—C16—C17−86.49 (18)
C4—C5—C6—C70.0 (3)C21—C16—C17—C180.5 (3)
C5—C6—C7—C80.0 (3)C14—C16—C17—C18−179.11 (16)
C6—C7—C8—C9178.23 (18)C16—C17—C18—C19−0.3 (3)
C6—C7—C8—C3−0.7 (3)C17—C18—C19—C20−0.2 (3)
C4—C3—C8—C9−177.71 (15)C17—C18—C19—C22179.83 (19)
C2—C3—C8—C91.2 (2)C18—C19—C20—C210.7 (3)
C4—C3—C8—C71.2 (2)C22—C19—C20—C21−179.40 (18)
C2—C3—C8—C7−179.93 (14)C19—C20—C21—C16−0.5 (3)
C7—C8—C9—C10−177.77 (16)C17—C16—C21—C200.0 (3)
C3—C8—C9—C101.1 (2)C14—C16—C21—C20179.53 (16)
C8—C9—C10—C11−1.0 (2)C12—C13—C24—O3−155.81 (15)
C3—C2—C11—O1−173.98 (12)C1—C13—C24—O3−33.5 (2)
C1—C2—C11—O11.4 (2)C14—C13—C24—O379.66 (18)
C3—C2—C11—C103.7 (2)C12—C13—C24—O227.28 (18)
C1—C2—C11—C10179.09 (13)C1—C13—C24—O2149.60 (13)
C9—C10—C11—O1176.41 (14)C14—C13—C24—O2−97.25 (15)
C9—C10—C11—C2−1.5 (2)C14—C15—N1—C23172.67 (14)
O1—C12—C13—C2466.46 (16)C14—C15—N1—C144.46 (15)
O1—C12—C13—C1−57.99 (15)C2—C1—N1—C2360.86 (17)
O1—C12—C13—C14−169.79 (11)C13—C1—N1—C23−177.89 (13)
N1—C1—C13—C24156.25 (12)C2—C1—N1—C15−173.59 (12)
C2—C1—C13—C24−80.75 (15)C13—C1—N1—C15−52.33 (13)
N1—C1—C13—C12−77.92 (13)C2—C11—O1—C12−13.3 (2)
C2—C1—C13—C1245.08 (15)C10—C11—O1—C12168.89 (12)
N1—C1—C13—C1439.14 (14)C13—C12—O1—C1142.84 (16)
C2—C1—C13—C14162.14 (11)O3—C24—O2—C25−1.3 (3)
C24—C13—C14—C16101.64 (15)C13—C24—O2—C25175.64 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C22—H22A···Cg1i0.962.843.788 (2)169

Symmetry codes: (i) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2823).

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