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In the title compound, C24H23NO5S, the pyran ring bearing the amino group adopts a flattened boat conformation. In the crystal structure, the mol­ecules are linked by N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015741/wn2027sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015741/wn2027Isup2.hkl
Contains datablock I

CCDC reference: 610921

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.137
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
Author Response: ...We have collected data on kappa IP diffractometer and processed using Denzo; and it is known that the DENZO image processing package has problems with certain strong reflections. They are often excluded from the data set leading to a lower value for the above parameter.

Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 25.03 From the CIF: _diffrn_reflns_theta_full 25.03 From the CIF: _reflns_number_total 3585 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3864 Completeness (_total/calc) 92.78% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: ... All the authors have been approved and each author has a genuine role for the contribution to this paper.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON.

Ethyl 2-amino-3-ethoxycarbonyl-7,8-dimethyl-4-[4-(methylsulfanyl)phenyl]- 5-oxo-4H-pyrano[3,2-c]chromene-3-carboxylate top
Crystal data top
C24H23NO5SF(000) = 920
Mr = 437.50Dx = 1.330 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2y b cCell parameters from 6677 reflections
a = 17.295 (5) Åθ = 2.4–25.0°
b = 7.494 (4) ŵ = 0.18 mm1
c = 17.127 (9) ÅT = 295 K
β = 100.220 (3)°Block, pale yellow
V = 2184.6 (18) Å30.25 × 0.22 × 0.22 mm
Z = 4
Data collection top
MacScience DIPLabo 32001
diffractometer
3119 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
Detector resolution: 10.0 pixels mm-1h = 2020
ω scansk = 88
6677 measured reflectionsl = 1819
3585 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.137 w = 1/[σ2(Fo2) + (0.0787P)2 + 0.3836P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max = 0.001
3585 reflectionsΔρmax = 0.35 e Å3
285 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.034 (3)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2, conventional R-factors R are based on F, with F set to zero for negative F^2. The observed criterion of F^2 > σ(F^2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2 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
xyzUiso*/Ueq
O10.03361 (8)0.7325 (2)0.07855 (8)0.0591 (5)
O70.13296 (7)0.63853 (19)0.31098 (7)0.0477 (5)
O170.14808 (9)0.8061 (3)0.04893 (9)0.0722 (7)
O200.37041 (8)0.7585 (2)0.39742 (8)0.0629 (6)
O210.38344 (7)0.8268 (2)0.27269 (8)0.0494 (5)
N180.22616 (10)0.6544 (3)0.41751 (10)0.0618 (7)
C20.11363 (11)0.7526 (3)0.09969 (11)0.0503 (7)
C30.15042 (10)0.7102 (2)0.17979 (10)0.0402 (6)
C40.23881 (10)0.7208 (2)0.20106 (10)0.0384 (6)
C50.26278 (10)0.7160 (3)0.29035 (11)0.0417 (6)
C60.21131 (10)0.6724 (3)0.33893 (10)0.0430 (6)
C80.10400 (10)0.6707 (2)0.23270 (10)0.0397 (6)
C90.01980 (10)0.6620 (3)0.21244 (11)0.0433 (6)
C100.03074 (11)0.6298 (3)0.26646 (13)0.0486 (7)
C110.11060 (11)0.6270 (3)0.23975 (14)0.0534 (7)
C120.14311 (11)0.6533 (3)0.16009 (14)0.0526 (7)
C130.09410 (11)0.6848 (3)0.10491 (13)0.0549 (7)
C140.01341 (11)0.6911 (3)0.13350 (12)0.0476 (6)
C150.23117 (12)0.6505 (3)0.13435 (16)0.0665 (9)
C160.12544 (14)0.7132 (5)0.01821 (16)0.0809 (10)
C190.34194 (11)0.7652 (3)0.32682 (11)0.0450 (6)
C220.46362 (11)0.8810 (3)0.30270 (13)0.0543 (7)
C230.50346 (13)0.9049 (3)0.23295 (14)0.0633 (8)
C240.27734 (9)0.5733 (2)0.15926 (10)0.0369 (5)
C250.26733 (11)0.3960 (3)0.17714 (12)0.0481 (7)
C260.30086 (12)0.2609 (3)0.13971 (12)0.0506 (7)
C270.34564 (10)0.3010 (3)0.08190 (10)0.0409 (6)
C280.35672 (10)0.4778 (3)0.06401 (10)0.0425 (6)
C290.32280 (10)0.6121 (3)0.10267 (11)0.0410 (6)
S300.38284 (3)0.11681 (8)0.03578 (3)0.0560 (2)
C310.43785 (14)0.2134 (4)0.03192 (15)0.0706 (9)
H40.255300.836000.182400.0460*
H100.010500.610500.319800.0580*
H110.143900.607000.275900.0640*
H15A0.248800.765400.113700.1000*
H15B0.255500.622700.179000.1000*
H15C0.245200.561600.094000.1000*
H16A0.082800.741200.008800.1220*
H16B0.162400.810000.012000.1220*
H16C0.151100.606400.004000.1220*
H18A0.273000.670900.443300.0740*
H18B0.188900.626200.442500.0740*
H22A0.490400.790500.338000.0650*
H22B0.464200.992100.331900.0650*
H23A0.504600.793000.205900.0950*
H23B0.556200.946100.250700.0950*
H23C0.475200.991100.197400.0950*
H250.237300.367000.215300.0580*
H260.293600.142700.153100.0610*
H280.386900.507200.026000.0510*
H290.330900.730600.090200.0490*
H31A0.404400.289900.068100.1060*
H31B0.458400.120600.061000.1060*
H31C0.480500.281900.003100.1060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0452 (7)0.0910 (12)0.0411 (8)0.0071 (7)0.0075 (6)0.0061 (7)
O70.0399 (7)0.0665 (10)0.0378 (8)0.0020 (6)0.0099 (5)0.0065 (6)
O170.0568 (9)0.1185 (15)0.0449 (9)0.0122 (9)0.0191 (7)0.0235 (8)
O200.0508 (8)0.0969 (13)0.0393 (9)0.0046 (8)0.0037 (6)0.0042 (7)
O210.0412 (7)0.0630 (9)0.0436 (8)0.0085 (6)0.0066 (5)0.0022 (6)
N180.0499 (9)0.1006 (15)0.0360 (10)0.0000 (9)0.0109 (7)0.0041 (9)
C20.0446 (10)0.0655 (14)0.0423 (11)0.0092 (9)0.0117 (8)0.0038 (9)
C30.0416 (9)0.0428 (10)0.0377 (10)0.0047 (7)0.0114 (7)0.0006 (7)
C40.0407 (9)0.0405 (10)0.0358 (10)0.0006 (7)0.0114 (7)0.0001 (7)
C50.0418 (9)0.0473 (11)0.0373 (10)0.0007 (8)0.0103 (7)0.0054 (7)
C60.0438 (9)0.0514 (12)0.0344 (11)0.0031 (8)0.0086 (7)0.0012 (8)
C80.0426 (9)0.0409 (10)0.0359 (10)0.0035 (7)0.0080 (7)0.0009 (7)
C90.0403 (9)0.0412 (11)0.0492 (11)0.0029 (8)0.0103 (8)0.0006 (8)
C100.0456 (10)0.0476 (12)0.0546 (12)0.0027 (8)0.0143 (8)0.0056 (8)
C110.0426 (10)0.0499 (13)0.0709 (15)0.0012 (8)0.0185 (9)0.0064 (9)
C120.0421 (10)0.0428 (12)0.0721 (14)0.0016 (8)0.0081 (9)0.0012 (9)
C130.0461 (10)0.0585 (14)0.0573 (13)0.0032 (9)0.0017 (9)0.0039 (10)
C140.0442 (10)0.0532 (12)0.0458 (11)0.0040 (8)0.0090 (8)0.0006 (8)
C150.0444 (11)0.0626 (15)0.0904 (18)0.0018 (10)0.0060 (11)0.0002 (12)
C160.0553 (13)0.119 (2)0.0622 (16)0.0077 (14)0.0065 (11)0.0021 (14)
C190.0450 (10)0.0508 (12)0.0399 (11)0.0031 (8)0.0092 (8)0.0060 (8)
C220.0423 (10)0.0614 (14)0.0573 (13)0.0083 (9)0.0039 (8)0.0061 (9)
C230.0526 (11)0.0685 (16)0.0696 (15)0.0101 (10)0.0132 (10)0.0068 (11)
C240.0346 (8)0.0438 (10)0.0327 (9)0.0009 (7)0.0074 (6)0.0013 (7)
C250.0510 (11)0.0497 (12)0.0490 (12)0.0045 (8)0.0234 (8)0.0017 (8)
C260.0605 (12)0.0404 (11)0.0549 (12)0.0034 (9)0.0212 (9)0.0019 (8)
C270.0367 (8)0.0483 (12)0.0372 (10)0.0030 (7)0.0054 (7)0.0042 (7)
C280.0408 (9)0.0515 (12)0.0381 (10)0.0011 (8)0.0152 (7)0.0020 (8)
C290.0431 (9)0.0415 (11)0.0402 (11)0.0012 (7)0.0125 (7)0.0030 (7)
S300.0615 (4)0.0522 (4)0.0563 (4)0.0091 (2)0.0162 (2)0.0092 (2)
C310.0704 (14)0.0854 (18)0.0626 (15)0.0199 (13)0.0296 (11)0.0052 (12)
Geometric parameters (Å, º) top
S30—C271.767 (2)C22—C231.492 (3)
S30—C311.779 (3)C24—C291.383 (2)
O1—C21.375 (2)C24—C251.381 (3)
O1—C141.384 (2)C25—C261.380 (3)
O7—C61.378 (2)C26—C271.394 (3)
O7—C81.367 (2)C27—C281.381 (3)
O17—C21.206 (3)C28—C291.390 (3)
O20—C191.223 (2)C4—H40.9804
O21—C191.351 (2)C10—H100.9298
O21—C221.449 (2)C11—H110.9295
N18—C61.331 (2)C15—H15A0.9598
N18—H18A0.8600C15—H15B0.9589
N18—H18B0.8608C15—H15C0.9596
C2—C31.442 (3)C16—H16A0.9607
C3—C81.346 (2)C16—H16B0.9602
C3—C41.509 (2)C16—H16C0.9604
C4—C241.532 (2)C22—H22A0.9699
C4—C51.512 (3)C22—H22B0.9704
C5—C61.362 (3)C23—H23A0.9599
C5—C191.448 (3)C23—H23B0.9599
C8—C91.437 (2)C23—H23C0.9598
C9—C141.389 (3)C25—H250.9298
C9—C101.402 (3)C26—H260.9291
C10—C111.376 (3)C28—H280.9303
C11—C121.394 (3)C29—H290.9298
C12—C131.397 (3)C31—H31A0.9592
C12—C151.509 (3)C31—H31B0.9596
C13—C161.503 (3)C31—H31C0.9602
C13—C141.395 (3)
S30···H23Ci3.0874C31···H282.6303
S30···H22Aii3.0809H4···O172.6852
S30···H18Aiii3.1143H4···O212.4681
O17···C293.332 (3)H4···H26x2.4680
O17···C243.180 (2)H4···H292.3579
O17···N18iv2.838 (2)H10···O72.5211
O20···N182.694 (2)H11···H15B2.3145
O21···C293.329 (2)H11···C3viii3.0759
O21···C243.080 (2)H11···H25vii2.5524
O1···H16A2.2863H15A···C162.9356
O7···H102.5211H15A···H16B2.5104
O17···H42.6852H15B···H112.3145
O17···H18Biv2.1296H15B···C5viii3.0990
O20···H22A2.4798H15B···C19viii3.0610
O20···H18A2.0872H15B···H25vii2.5546
O20···H28v2.7913H15C···C162.8670
O20···H22B2.7570H15C···H16C2.5589
O20···H31Cvi2.8809H15C···C28ix3.0461
O21···H42.4681H16A···O12.2863
N18···O202.694 (2)H16B···C152.8494
N18···O17v2.838 (2)H16B···H15A2.5104
C3···C11vii3.531 (3)H16B···H18Bvii2.5611
C5···C15vii3.580 (3)H16C···C152.9675
C8···C11vii3.451 (3)H16C···H15C2.5589
C9···C10vii3.526 (3)H18A···O202.0872
C10···C9viii3.526 (3)H18A···C192.5971
C11···C3viii3.531 (3)H18A···S30xi3.1143
C11···C8viii3.451 (3)H18B···H16Bviii2.5611
C15···C19viii3.592 (3)H18B···O17v2.1296
C15···C5viii3.580 (3)H22A···O202.4798
C19···C15vii3.592 (3)H22A···S30vi3.0809
C22···C28vi3.588 (3)H22A···C27vi2.9238
C22···C27vi3.583 (3)H22A···H23Cii2.4256
C24···O213.080 (2)H22B···O202.7570
C24···O173.180 (2)H22B···H23Avi2.4329
C27···C22ii3.583 (3)H23A···H22Bii2.4329
C28···C22ii3.588 (3)H23C···S30x3.0874
C29···O173.332 (3)H23C···H22Avi2.4256
C29···O213.329 (2)H25···C32.9863
C3···H11vii3.0759H25···C52.9130
C3···H252.9863H25···C11viii3.0377
C5···H252.9130H25···C15viii3.0613
C5···H15Bvii3.0990H25···H11viii2.5524
C11···H25vii3.0377H25···H15Bviii2.5546
C15···H16C2.9675H26···H4i2.4680
C15···H31Aix3.0425H28···C312.6303
C15···H25vii3.0613H28···H31A2.3482
C15···H16B2.8494H28···H31C2.4507
C16···H15C2.8670H28···O20iv2.7913
C16···H15A2.9356H29···H42.3579
C19···H15Bvii3.0610H31A···C282.9059
C19···H18A2.5971H31A···H282.3482
C27···H22Aii2.9238H31A···C15ix3.0425
C28···H31A2.9059H31C···C282.9887
C28···H15Cix3.0461H31C···H282.4507
C28···H31C2.9887H31C···O20ii2.8809
C27—S30—C31104.64 (12)S30—C27—C26116.19 (17)
C2—O1—C14122.06 (15)C26—C27—C28118.75 (19)
C6—O7—C8118.35 (14)C27—C28—C29120.13 (17)
C19—O21—C22116.37 (15)C24—C29—C28121.46 (19)
C6—N18—H18A119.98C3—C4—H4107.96
C6—N18—H18B120.02C5—C4—H4107.89
H18A—N18—H18B120.00C24—C4—H4107.89
O17—C2—C3124.61 (18)C9—C10—H10120.34
O1—C2—O17116.70 (17)C11—C10—H10120.33
O1—C2—C3118.69 (16)C10—C11—H11119.02
C2—C3—C8118.29 (16)C12—C11—H11118.99
C2—C3—C4118.37 (15)C12—C15—H15A109.48
C4—C3—C8123.27 (15)C12—C15—H15B109.46
C3—C4—C5109.09 (14)C12—C15—H15C109.47
C3—C4—C24110.80 (13)H15A—C15—H15B109.46
C5—C4—C24113.04 (14)H15A—C15—H15C109.53
C6—C5—C19117.91 (17)H15B—C15—H15C109.44
C4—C5—C6122.14 (16)C13—C16—H16A109.49
C4—C5—C19119.91 (16)C13—C16—H16B109.44
O7—C6—N18109.50 (15)C13—C16—H16C109.49
O7—C6—C5122.75 (15)H16A—C16—H16B109.54
N18—C6—C5127.75 (17)H16A—C16—H16C109.36
C3—C8—C9123.18 (16)H16B—C16—H16C109.51
O7—C8—C9114.08 (15)O21—C22—H22A110.26
O7—C8—C3122.73 (16)O21—C22—H22B110.19
C10—C9—C14118.09 (17)C23—C22—H22A110.23
C8—C9—C14117.00 (16)C23—C22—H22B110.22
C8—C9—C10124.90 (17)H22A—C22—H22B108.58
C9—C10—C11119.3 (2)C22—C23—H23A109.48
C10—C11—C12122.0 (2)C22—C23—H23B109.45
C11—C12—C13119.87 (18)C22—C23—H23C109.46
C11—C12—C15119.7 (2)H23A—C23—H23B109.52
C13—C12—C15120.5 (2)H23A—C23—H23C109.48
C12—C13—C16122.45 (19)H23B—C23—H23C109.44
C12—C13—C14117.2 (2)C24—C25—H25119.23
C14—C13—C16120.32 (19)C26—C25—H25119.22
O1—C14—C9120.38 (17)C25—C26—H26119.90
O1—C14—C13116.15 (18)C27—C26—H26119.83
C9—C14—C13123.46 (18)C27—C28—H28119.98
O21—C19—C5111.58 (16)C29—C28—H28119.89
O20—C19—C5126.87 (18)C24—C29—H29119.30
O20—C19—O21121.53 (18)C28—C29—H29119.24
O21—C22—C23107.37 (17)S30—C31—H31A109.46
C4—C24—C25120.55 (15)S30—C31—H31B109.48
C4—C24—C29121.62 (15)S30—C31—H31C109.47
C25—C24—C29117.83 (17)H31A—C31—H31B109.53
C24—C25—C26121.55 (18)H31A—C31—H31C109.44
C25—C26—C27120.3 (2)H31B—C31—H31C109.44
S30—C27—C28125.05 (14)
C31—S30—C27—C26178.80 (16)C6—C5—C19—O21172.11 (19)
C31—S30—C27—C282.23 (19)C4—C5—C19—O215.7 (3)
C2—O1—C14—C13176.40 (19)C19—C5—C6—O7174.27 (19)
C14—O1—C2—C36.9 (3)C4—C5—C6—N18176.1 (2)
C2—O1—C14—C92.3 (3)C19—C5—C6—N186.1 (4)
C14—O1—C2—O17172.8 (2)O7—C8—C9—C14179.17 (18)
C6—O7—C8—C39.4 (2)O7—C8—C9—C102.1 (3)
C6—O7—C8—C9169.49 (17)C3—C8—C9—C10176.78 (19)
C8—O7—C6—C58.0 (3)C3—C8—C9—C142.0 (3)
C8—O7—C6—N18172.36 (17)C10—C9—C14—O1176.7 (2)
C22—O21—C19—C5179.70 (17)C8—C9—C14—O12.2 (3)
C22—O21—C19—O201.1 (3)C10—C9—C14—C131.9 (3)
C19—O21—C22—C23167.64 (18)C8—C9—C14—C13179.2 (2)
O17—C2—C3—C8172.8 (2)C14—C9—C10—C110.4 (3)
O1—C2—C3—C4175.99 (16)C8—C9—C10—C11179.2 (2)
O17—C2—C3—C44.4 (3)C9—C10—C11—C120.7 (3)
O1—C2—C3—C86.8 (3)C10—C11—C12—C15179.4 (2)
C2—C3—C4—C2468.67 (19)C10—C11—C12—C130.4 (3)
C4—C3—C8—C9179.52 (16)C15—C12—C13—C161.3 (4)
C2—C3—C4—C5166.27 (17)C15—C12—C13—C14178.0 (2)
C4—C3—C8—O70.8 (2)C11—C12—C13—C141.0 (3)
C2—C3—C8—C92.5 (3)C11—C12—C13—C16179.7 (2)
C8—C3—C4—C24114.32 (17)C12—C13—C14—O1176.45 (19)
C8—C3—C4—C510.7 (2)C16—C13—C14—C9178.4 (2)
C2—C3—C8—O7176.24 (16)C12—C13—C14—C92.2 (3)
C3—C4—C5—C19165.76 (18)C16—C13—C14—O12.9 (3)
C24—C4—C5—C6111.8 (2)C4—C24—C25—C26179.38 (17)
C5—C4—C24—C2557.7 (2)C4—C24—C29—C28179.03 (16)
C3—C4—C5—C611.9 (3)C25—C24—C29—C280.8 (3)
C24—C4—C5—C1970.5 (2)C29—C24—C25—C260.5 (3)
C3—C4—C24—C29114.74 (17)C24—C25—C26—C270.5 (3)
C3—C4—C24—C2565.1 (2)C25—C26—C27—S30177.96 (15)
C5—C4—C24—C29122.46 (18)C25—C26—C27—C281.1 (3)
C6—C5—C19—O206.4 (4)S30—C27—C28—C29178.21 (14)
C4—C5—C19—O20175.9 (2)C26—C27—C28—C290.7 (3)
C4—C5—C6—O73.4 (3)C27—C28—C29—C240.2 (3)
Symmetry codes: (i) x, y1, z; (ii) x+1, y1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x, y+3/2, z1/2; (v) x, y+3/2, z+1/2; (vi) x+1, y+1/2, z+1/2; (vii) x, y+1/2, z+1/2; (viii) x, y1/2, z+1/2; (ix) x, y+1, z; (x) x, y+1, z; (xi) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N18—H18A···O200.862.092.694 (2)127
N18—H18B···O17v0.862.132.838 (2)139
C16—H16A···O10.962.292.765 (3)110
Symmetry code: (v) x, y+3/2, z+1/2.
 

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