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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Apr 18;68(Pt 5):o1430. doi: 10.1107/S1600536812015656

Dimethyl 3-(cyclo­propyl­carbon­yl)pyrrolo­[2,1-a]isoquinoline-1,2-dicarboxyl­ate

Honglong Xing a, Fan Tang a, Wei Wang b,*
PMCID: PMC3344550  PMID: 22590312

Abstract

In the mol­ecular structure of the title compound, C20H17NO5, two intra­molecular C—H⋯O hydrogen bond generate six- and seven-membered ring motifs. The dihedral angles between the almost planar 13-atom triple-fused-ring system (r.m.s. deviation = 0.003 Å) and the planes of the two meth­oxy­carbonyl substituents are 61.7 (2) and 33.01 (10)°.

Related literature  

For chemical background, see: Michael (2004 ▶); Sriram et al. (2005 ▶); Alonso et al. (1985 ▶). For the biological activity of indolizine derivatives, see: Shen et al. (2010 ▶).graphic file with name e-68-o1430-scheme1.jpg

Experimental  

Crystal data  

  • C20H17NO5

  • M r = 351.35

  • Monoclinic, Inline graphic

  • a = 7.5910 (15) Å

  • b = 18.436 (4) Å

  • c = 12.162 (2) Å

  • β = 94.43 (3)°

  • V = 1697.0 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection  

  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995 ▶) T min = 0.971, T max = 0.990

  • 3321 measured reflections

  • 3078 independent reflections

  • 2060 reflections with I > 2σ(I)

  • R int = 0.048

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.056

  • wR(F 2) = 0.179

  • S = 1.01

  • 3078 reflections

  • 235 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.24 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015656/ff2061sup1.cif

e-68-o1430-sup1.cif (20.6KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015656/ff2061Isup2.hkl

e-68-o1430-Isup2.hkl (151KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812015656/ff2061Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C13—H13A⋯O1 0.93 2.27 2.872 (4) 122
C20—H20A⋯O4 0.93 2.18 3.019 (4) 150
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Acknowledgments

We greatly appreciate the financial support of the Foundation of the Key Laboratory for Advanced Technology in Environmental Protection of Jiangsu Province (AE201017).

supplementary crystallographic information

Comment

The indolizine and hydrogenated indolizine structures are found in many alkaloids such as amorine, crythraline, swainsonine, cryptaustoline, cryptowoline (Sriram et al. 2005), camptothesin(Michael, 2004), nuevamine (Alonso et al., 1985), etc. These natural and many synthetic indolizine derivatives have been found to have a variety of biological activity (Shen et al., 2010).

We report here the synthesis and crystal structure of the title compound (I). The molecular structure of (I) is shown in Fig.1. In the title compound, intramolecular C13 —H13A···O1 and C20—H20A···O4 hydrogen bond generates extra two ring motifs. The dihedral angle between the indolizine ring system and the C20—H20A···O4 plane is 20.40 (4)°.

Experimental

A mixture of the 2-(2-cyclopropyl-2-oxoethyl)isoquinolinium bromide (10 mmol), acrylonitrile (40 mmol), triethylamine (2 ml) and TPCD (4 g) in DMF (40 ml) was heated at 90° C for 5 h. After cooling, the reaction mixture was poured into an aqueous hydrochloric acid solution (5%, 100 ml), the precipitated crude product was collected by filtration and further purified by silica gel column chromatography with petroleum ether (bp 60–90 °C)-ethyl acetate as eluents. Yellow crystal. m.p. 388–389 K, Yield 76%. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in petroleum ether -ethyl acetate(4:1), at room temperature.

Refinement

The H atoms were fixed geometrically and were treated as riding on their parent C atoms, with C—H distances in the range of 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(parent atom), or Uiso(H) = 1.5Ueq(Cmethyl).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound, with 30% probability displacement ellipsoids. Dashed lines indicate hydrogen bonds.

Crystal data

C20H17NO5 F(000) = 736
Mr = 351.35 Dx = 1.375 Mg m−3
Monoclinic, P21/c Melting point: 388 K
Hall symbol: -P 2ybc Mo Kα radiation, λ = 0.71073 Å
a = 7.5910 (15) Å Cell parameters from 25 reflections
b = 18.436 (4) Å θ = 9–12°
c = 12.162 (2) Å µ = 0.10 mm−1
β = 94.43 (3)° T = 293 K
V = 1697.0 (6) Å3 Block, yellow
Z = 4 0.30 × 0.20 × 0.10 mm
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Data collection

Enraf–Nonius CAD-4 diffractometer 2060 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.048
Graphite monochromator θmax = 25.3°, θmin = 2.0°
ω/2θ scans h = 0→9
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995) k = 0→22
Tmin = 0.971, Tmax = 0.990 l = −14→14
3321 measured reflections 3 standard reflections every 200 reflections
3078 independent reflections intensity decay: 1%
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179 H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1P)2 + 0.4P] where P = (Fo2 + 2Fc2)/3
3078 reflections (Δ/σ)max < 0.001
235 parameters Δρmax = 0.30 e Å−3
0 restraints Δρmin = −0.24 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
N 0.2043 (3) 0.45752 (11) 0.56131 (17) 0.0407 (5)
O1 0.0490 (3) 0.31335 (12) 0.57398 (18) 0.0729 (7)
C1 0.0128 (5) 0.2518 (2) 0.7977 (3) 0.0763 (10)
H1A 0.0035 0.2474 0.8765 0.092*
H1B −0.0987 0.2485 0.7533 0.092*
O2 0.3127 (2) 0.44915 (12) 0.92593 (15) 0.0583 (6)
C2 0.1687 (5) 0.22111 (19) 0.7524 (4) 0.0815 (11)
H2A 0.1537 0.1991 0.6799 0.098*
H2B 0.2560 0.1979 0.8032 0.098*
O3 0.0196 (3) 0.44054 (13) 0.88912 (17) 0.0657 (6)
C3 0.1495 (4) 0.30195 (16) 0.7597 (3) 0.0591 (8)
H3A 0.2247 0.3260 0.8179 0.071*
O4 0.4069 (3) 0.64344 (13) 0.76734 (18) 0.0715 (7)
C4 0.1160 (4) 0.34276 (15) 0.6567 (2) 0.0463 (7)
O5 0.1973 (3) 0.59404 (11) 0.86128 (17) 0.0613 (6)
C5 0.2880 (5) 0.4387 (3) 1.0410 (3) 0.0879 (13)
H5A 0.4009 0.4381 1.0824 0.132*
H5B 0.2287 0.3934 1.0507 0.132*
H5C 0.2179 0.4776 1.0667 0.132*
C6 0.1646 (4) 0.45114 (15) 0.8593 (2) 0.0462 (7)
C7 0.2330 (5) 0.64687 (18) 0.9471 (3) 0.0694 (10)
H7A 0.1510 0.6407 1.0026 0.104*
H7B 0.2206 0.6947 0.9164 0.104*
H7C 0.3513 0.6405 0.9795 0.104*
C8 0.3006 (3) 0.59626 (15) 0.7761 (2) 0.0452 (7)
C9 0.2639 (3) 0.53321 (14) 0.7048 (2) 0.0403 (6)
C10 0.2004 (3) 0.46707 (14) 0.7437 (2) 0.0403 (6)
C11 0.1670 (3) 0.41976 (14) 0.6564 (2) 0.0405 (6)
C12 0.2688 (3) 0.52648 (14) 0.5891 (2) 0.0406 (6)
C13 0.1793 (3) 0.43333 (16) 0.4534 (2) 0.0472 (7)
H13A 0.1353 0.3870 0.4387 0.057*
C14 0.2183 (4) 0.47657 (17) 0.3706 (2) 0.0555 (8)
H14A 0.1957 0.4607 0.2983 0.067*
C15 0.2945 (4) 0.54702 (17) 0.3911 (2) 0.0512 (7)
C16 0.3216 (3) 0.57249 (15) 0.5008 (2) 0.0449 (7)
C17 0.3413 (4) 0.5916 (2) 0.3040 (3) 0.0644 (9)
H17A 0.3216 0.5754 0.2317 0.077*
C18 0.4146 (4) 0.6579 (2) 0.3238 (3) 0.0693 (10)
H18A 0.4429 0.6871 0.2654 0.083*
C19 0.4473 (4) 0.68183 (18) 0.4315 (3) 0.0653 (9)
H19A 0.5020 0.7264 0.4449 0.078*
C20 0.4002 (4) 0.64068 (16) 0.5189 (3) 0.0553 (8)
H20A 0.4206 0.6582 0.5905 0.066*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N 0.0414 (12) 0.0421 (12) 0.0390 (12) 0.0036 (10) 0.0048 (9) −0.0006 (10)
O1 0.0976 (17) 0.0614 (14) 0.0594 (14) −0.0228 (13) 0.0031 (12) −0.0076 (11)
C1 0.076 (2) 0.080 (3) 0.075 (2) −0.0009 (19) 0.0169 (19) 0.0190 (19)
O2 0.0539 (12) 0.0747 (15) 0.0457 (12) 0.0098 (11) 0.0005 (9) 0.0041 (10)
C2 0.101 (3) 0.053 (2) 0.092 (3) 0.0147 (19) 0.022 (2) 0.0156 (19)
O3 0.0523 (12) 0.0861 (16) 0.0604 (13) −0.0108 (12) 0.0159 (10) −0.0020 (12)
C3 0.074 (2) 0.0412 (16) 0.061 (2) −0.0008 (15) −0.0017 (16) 0.0013 (14)
O4 0.0759 (15) 0.0702 (15) 0.0703 (15) −0.0316 (13) 0.0186 (12) −0.0128 (12)
C4 0.0449 (15) 0.0450 (16) 0.0495 (16) 0.0019 (13) 0.0059 (12) −0.0051 (13)
O5 0.0749 (14) 0.0487 (12) 0.0634 (14) −0.0122 (10) 0.0248 (11) −0.0177 (10)
C5 0.092 (3) 0.130 (4) 0.0406 (19) 0.021 (3) −0.0004 (17) 0.008 (2)
C6 0.0499 (16) 0.0419 (15) 0.0471 (16) 0.0023 (13) 0.0060 (13) −0.0026 (12)
C7 0.086 (2) 0.062 (2) 0.062 (2) −0.0102 (18) 0.0194 (18) −0.0194 (17)
C8 0.0352 (13) 0.0472 (16) 0.0531 (17) −0.0003 (13) 0.0036 (12) 0.0001 (13)
C9 0.0349 (13) 0.0427 (15) 0.0437 (15) 0.0056 (11) 0.0049 (11) −0.0003 (12)
C10 0.0379 (13) 0.0417 (15) 0.0413 (15) 0.0045 (11) 0.0035 (11) 0.0006 (11)
C11 0.0373 (13) 0.0423 (15) 0.0421 (15) 0.0050 (11) 0.0038 (11) 0.0011 (12)
C12 0.0339 (13) 0.0402 (14) 0.0479 (16) 0.0071 (11) 0.0039 (11) 0.0020 (12)
C13 0.0448 (15) 0.0531 (17) 0.0428 (16) 0.0060 (13) −0.0014 (12) −0.0032 (13)
C14 0.0547 (17) 0.069 (2) 0.0426 (17) 0.0116 (15) 0.0020 (13) −0.0036 (15)
C15 0.0462 (15) 0.0619 (19) 0.0461 (17) 0.0136 (14) 0.0069 (12) 0.0123 (14)
C16 0.0330 (13) 0.0472 (16) 0.0551 (17) 0.0110 (12) 0.0066 (11) 0.0095 (13)
C17 0.0523 (18) 0.083 (2) 0.059 (2) 0.0119 (17) 0.0109 (14) 0.0175 (18)
C18 0.057 (2) 0.078 (2) 0.075 (2) 0.0110 (18) 0.0161 (17) 0.034 (2)
C19 0.0588 (19) 0.0517 (18) 0.087 (3) 0.0033 (15) 0.0161 (17) 0.0196 (18)
C20 0.0491 (16) 0.0516 (17) 0.066 (2) 0.0040 (14) 0.0112 (14) 0.0080 (15)
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Geometric parameters (Å, º)

N—C13 1.385 (3) C6—C10 1.483 (4)
N—C12 1.395 (3) C7—H7A 0.9600
N—C11 1.398 (3) C7—H7B 0.9600
O1—C4 1.218 (3) C7—H7C 0.9600
C1—C2 1.458 (5) C8—C9 1.464 (4)
C1—C3 1.490 (5) C9—C10 1.406 (4)
C1—H1A 0.9700 C9—C12 1.416 (4)
C1—H1B 0.9700 C10—C11 1.382 (4)
O2—C6 1.334 (3) C12—C16 1.449 (4)
O2—C5 1.440 (4) C13—C14 1.335 (4)
C2—C3 1.501 (4) C13—H13A 0.9300
C2—H2A 0.9700 C14—C15 1.436 (4)
C2—H2B 0.9700 C14—H14A 0.9300
O3—C6 1.201 (3) C15—C17 1.408 (4)
C3—C4 1.467 (4) C15—C16 1.414 (4)
C3—H3A 0.9800 C16—C20 1.402 (4)
O4—C8 1.197 (3) C17—C18 1.356 (5)
C4—C11 1.472 (4) C17—H17A 0.9300
O5—C8 1.347 (3) C18—C19 1.387 (5)
O5—C7 1.438 (3) C18—H18A 0.9300
C5—H5A 0.9600 C19—C20 1.376 (4)
C5—H5B 0.9600 C19—H19A 0.9300
C5—H5C 0.9600 C20—H20A 0.9300
C13—N—C12 122.9 (2) H7B—C7—H7C 109.5
C13—N—C11 127.0 (2) O4—C8—O5 121.8 (3)
C12—N—C11 110.1 (2) O4—C8—C9 128.5 (3)
C2—C1—C3 61.2 (2) O5—C8—C9 109.6 (2)
C2—C1—H1A 117.6 C10—C9—C12 107.1 (2)
C3—C1—H1A 117.6 C10—C9—C8 122.9 (2)
C2—C1—H1B 117.6 C12—C9—C8 129.8 (2)
C3—C1—H1B 117.6 C11—C10—C9 109.7 (2)
H1A—C1—H1B 114.8 C11—C10—C6 124.6 (2)
C6—O2—C5 115.3 (2) C9—C10—C6 125.7 (2)
C1—C2—C3 60.5 (2) C10—C11—N 106.5 (2)
C1—C2—H2A 117.7 C10—C11—C4 129.8 (2)
C3—C2—H2A 117.7 N—C11—C4 123.5 (2)
C1—C2—H2B 117.7 N—C12—C9 106.6 (2)
C3—C2—H2B 117.7 N—C12—C16 117.8 (2)
H2A—C2—H2B 114.8 C9—C12—C16 135.7 (3)
C4—C3—C1 120.3 (3) C14—C13—N 120.0 (3)
C4—C3—C2 118.0 (3) C14—C13—H13A 120.0
C1—C3—C2 58.3 (2) N—C13—H13A 120.0
C4—C3—H3A 116.0 C13—C14—C15 121.3 (3)
C1—C3—H3A 116.0 C13—C14—H14A 119.4
C2—C3—H3A 116.0 C15—C14—H14A 119.4
O1—C4—C3 120.7 (3) C17—C15—C16 119.3 (3)
O1—C4—C11 121.4 (3) C17—C15—C14 121.3 (3)
C3—C4—C11 117.9 (2) C16—C15—C14 119.4 (3)
C8—O5—C7 116.7 (2) C20—C16—C15 118.4 (3)
O2—C5—H5A 109.5 C20—C16—C12 123.1 (3)
O2—C5—H5B 109.5 C15—C16—C12 118.5 (3)
H5A—C5—H5B 109.5 C18—C17—C15 121.1 (3)
O2—C5—H5C 109.5 C18—C17—H17A 119.4
H5A—C5—H5C 109.5 C15—C17—H17A 119.4
H5B—C5—H5C 109.5 C17—C18—C19 119.7 (3)
O3—C6—O2 124.1 (3) C17—C18—H18A 120.1
O3—C6—C10 123.9 (3) C19—C18—H18A 120.1
O2—C6—C10 111.9 (2) C20—C19—C18 121.1 (3)
O5—C7—H7A 109.5 C20—C19—H19A 119.5
O5—C7—H7B 109.5 C18—C19—H19A 119.5
H7A—C7—H7B 109.5 C19—C20—C16 120.4 (3)
O5—C7—H7C 109.5 C19—C20—H20A 119.8
H7A—C7—H7C 109.5 C16—C20—H20A 119.8
C2—C1—C3—C4 106.2 (3) C3—C4—C11—C10 −19.1 (4)
C1—C2—C3—C4 −110.1 (3) O1—C4—C11—N −23.9 (4)
C1—C3—C4—O1 −44.0 (4) C3—C4—C11—N 155.6 (2)
C2—C3—C4—O1 23.8 (5) C13—N—C12—C9 175.8 (2)
C1—C3—C4—C11 136.5 (3) C11—N—C12—C9 −2.7 (3)
C2—C3—C4—C11 −155.7 (3) C13—N—C12—C16 −3.9 (3)
C5—O2—C6—O3 −4.7 (4) C11—N—C12—C16 177.5 (2)
C5—O2—C6—C10 176.1 (3) C10—C9—C12—N 1.4 (3)
C7—O5—C8—O4 −6.1 (4) C8—C9—C12—N −173.7 (2)
C7—O5—C8—C9 172.0 (3) C10—C9—C12—C16 −178.9 (3)
O4—C8—C9—C10 150.7 (3) C8—C9—C12—C16 6.0 (5)
O5—C8—C9—C10 −27.3 (3) C12—N—C13—C14 0.4 (4)
O4—C8—C9—C12 −34.9 (5) C11—N—C13—C14 178.7 (2)
O5—C8—C9—C12 147.1 (3) N—C13—C14—C15 3.1 (4)
C12—C9—C10—C11 0.3 (3) C13—C14—C15—C17 177.8 (3)
C8—C9—C10—C11 175.9 (2) C13—C14—C15—C16 −2.9 (4)
C12—C9—C10—C6 −176.5 (2) C17—C15—C16—C20 −2.2 (4)
C8—C9—C10—C6 −1.0 (4) C14—C15—C16—C20 178.5 (2)
O3—C6—C10—C11 −63.4 (4) C17—C15—C16—C12 178.6 (2)
O2—C6—C10—C11 115.8 (3) C14—C15—C16—C12 −0.8 (4)
O3—C6—C10—C9 113.0 (3) N—C12—C16—C20 −175.2 (2)
O2—C6—C10—C9 −67.8 (3) C9—C12—C16—C20 5.1 (4)
C9—C10—C11—N −2.0 (3) N—C12—C16—C15 4.0 (3)
C6—C10—C11—N 174.9 (2) C9—C12—C16—C15 −175.7 (3)
C9—C10—C11—C4 173.5 (2) C16—C15—C17—C18 1.2 (4)
C6—C10—C11—C4 −9.6 (4) C14—C15—C17—C18 −179.4 (3)
C13—N—C11—C10 −175.5 (2) C15—C17—C18—C19 1.2 (5)
C12—N—C11—C10 2.9 (3) C17—C18—C19—C20 −2.6 (5)
C13—N—C11—C4 8.6 (4) C18—C19—C20—C16 1.6 (5)
C12—N—C11—C4 −172.9 (2) C15—C16—C20—C19 0.8 (4)
O1—C4—C11—C10 161.3 (3) C12—C16—C20—C19 −180.0 (3)
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
C13—H13A···O1 0.93 2.27 2.872 (4) 122
C20—H20A···O4 0.93 2.18 3.019 (4) 150
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2061).

References

  1. Alonso, R., Castedo, L. & Dominguez, D. (1985). Tetrahedron Lett. 26, 2925–2928.
  2. Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  3. Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  4. Michael, J. P. (2004). Nat. Prod. Rep. 21, 625–649. [DOI] [PubMed]
  5. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  6. Shen, Y. M., Lv, P. C., Chen, W., Liu, P. G., Zhang, M. Z. & Zhu, H. L. (2010). Eur. J. Med. Chem. 45, 3184–3190. [DOI] [PubMed]
  7. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
  8. Sriram, D., Yogeeswari, P., Thirumurugan, R. & Bal, T. R. (2005). Nat. Prod. Res. 19, 393–412. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015656/ff2061sup1.cif

e-68-o1430-sup1.cif (20.6KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015656/ff2061Isup2.hkl

e-68-o1430-Isup2.hkl (151KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812015656/ff2061Isup3.cml

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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