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The title compound, [Zn(NO3)(C8H8N2O)2]NO3·H2O, consists of a tris-chelated zinc cation and a nitrate anion, along with an uncoordinated water mol­ecule. These inter­act through O—H...O and N—H...O hydrogen bonds, giving rise to a three-dimensional network structure. The ZnII ion has an octa­hedral coordination.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051166/ci2231sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051166/ci2231Isup2.hkl
Contains datablock I

CCDC reference: 633647

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.114
  • Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT731_ALERT_1_B Bond Calc 0.85(5), Rep 0.850(10) ...... 5.00 su-Ra O1 -H1O 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.85(5), Rep 0.850(10) ...... 5.00 su-Ra O1 -H1O 1.555 1.555 PLAT736_ALERT_1_B H...A Calc 1.80(5), Rep 1.800(10) ...... 5.00 su-Ra H1O -O1W 1.555 1.555
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - O4 .. 7.75 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N6 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Ra O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O1W -H1W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra N2 -H2N 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra N4 -H4N 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Ra O1W -H1# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O1W -H2# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra N2 -H2N 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra N4 -H4N 1.555 1.555
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 14 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Bis[(1H-benzimidazol-2-yl)methanol-κ2N,O](nitrato-κ2O,O')zinc(II) nitrate monohydrate top
Crystal data top
[Zn(NO3)(C8H8N2O)2]NO3·H2OZ = 2
Mr = 503.73F(000) = 516
Triclinic, P1Dx = 1.683 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2287 (8) ÅCell parameters from 1775 reflections
b = 9.6745 (9) Åθ = 2.6–25.3°
c = 13.542 (1) ŵ = 1.30 mm1
α = 81.506 (2)°T = 293 K
β = 80.678 (2)°Plate, pale yellow
γ = 69.867 (2)°0.20 × 0.15 × 0.08 mm
V = 993.89 (15) Å3
Data collection top
Bruker APEX2 area-detector
diffractometer
3444 independent reflections
Radiation source: fine-focus sealed tube2947 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 89
Tmin = 0.781, Tmax = 0.903k = 711
5025 measured reflectionsl = 1416
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0636P)2 + 0.1377P]
where P = (Fo2 + 2Fc2)/3
3444 reflections(Δ/σ)max = 0.001
313 parametersΔρmax = 0.42 e Å3
6 restraintsΔρmin = 0.38 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.63068 (5)0.28762 (4)0.71867 (3)0.03887 (16)
O10.7129 (4)0.4602 (3)0.61315 (18)0.0498 (6)
O20.8274 (4)0.1249 (3)0.80316 (19)0.0552 (7)
O30.3507 (3)0.3877 (3)0.70619 (18)0.0528 (6)
O40.4400 (4)0.1801 (3)0.7952 (2)0.0597 (7)
O50.1635 (4)0.2852 (4)0.7842 (2)0.0794 (9)
O61.0456 (4)0.1810 (3)0.23550 (19)0.0685 (8)
O70.9411 (4)0.3797 (3)0.1372 (2)0.0639 (8)
O81.0147 (4)0.1678 (3)0.0834 (2)0.0733 (9)
O1w0.9389 (4)0.5498 (4)0.6807 (2)0.0660 (8)
N10.7096 (3)0.1969 (3)0.58860 (18)0.0362 (6)
N20.8324 (4)0.1899 (3)0.4307 (2)0.0428 (7)
N30.6455 (3)0.3992 (3)0.82755 (18)0.0364 (6)
N40.7730 (4)0.4208 (3)0.9528 (2)0.0436 (7)
N50.3140 (4)0.2837 (4)0.7627 (2)0.0518 (8)
N60.9990 (4)0.2446 (4)0.1516 (2)0.0480 (7)
C10.7183 (4)0.0643 (4)0.5560 (2)0.0366 (7)
C20.6608 (4)0.0497 (4)0.6050 (3)0.0428 (8)
H20.60900.04740.67140.051*
C30.6835 (5)0.1657 (4)0.5515 (3)0.0504 (9)
H30.64390.24270.58210.060*
C40.7641 (5)0.1721 (4)0.4527 (3)0.0531 (9)
H40.77820.25380.41950.064*
C50.8235 (5)0.0603 (4)0.4030 (3)0.0482 (9)
H50.87830.06470.33730.058*
C60.7972 (4)0.0583 (4)0.4562 (2)0.0395 (8)
C70.7782 (4)0.2673 (4)0.5116 (2)0.0378 (7)
C80.7888 (5)0.4168 (4)0.5156 (3)0.0496 (9)
H8A0.90940.41380.50390.059*
H8B0.72580.48670.46450.059*
C90.5821 (4)0.5475 (4)0.8472 (2)0.0377 (7)
C100.4643 (5)0.6696 (4)0.8017 (3)0.0469 (9)
H100.40820.66120.74960.056*
C110.4330 (5)0.8044 (4)0.8362 (3)0.0564 (10)
H110.35440.88860.80680.068*
C120.5167 (6)0.8169 (4)0.9142 (3)0.0610 (11)
H120.49360.91000.93490.073*
C130.6315 (5)0.6975 (4)0.9613 (3)0.0539 (10)
H130.68550.70691.01400.065*
C140.6637 (4)0.5609 (4)0.9267 (2)0.0417 (8)
C150.7580 (4)0.3290 (4)0.8921 (2)0.0389 (7)
C160.8541 (5)0.1691 (4)0.8933 (2)0.0460 (8)
H16A0.97730.14970.89550.055*
H16B0.81010.11540.95170.055*
H1O0.782 (5)0.485 (6)0.641 (4)0.11 (2)*
H2O0.855 (5)0.0325 (12)0.808 (3)0.056 (12)*
H1W10.996 (6)0.478 (4)0.719 (3)0.084 (17)*
H1W20.900 (6)0.628 (3)0.711 (3)0.090 (19)*
H2N0.881 (6)0.218 (5)0.3748 (19)0.088 (16)*
H4N0.837 (4)0.393 (4)1.0003 (19)0.048 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0469 (3)0.0401 (3)0.0314 (2)0.01608 (18)0.00224 (16)0.00750 (16)
O10.0711 (18)0.0497 (15)0.0372 (13)0.0326 (13)0.0014 (12)0.0081 (11)
O20.0726 (18)0.0408 (16)0.0455 (14)0.0046 (13)0.0153 (12)0.0089 (12)
O30.0508 (15)0.0615 (17)0.0481 (15)0.0217 (13)0.0064 (11)0.0033 (13)
O40.0673 (18)0.0543 (17)0.0574 (16)0.0234 (14)0.0033 (13)0.0012 (13)
O50.0532 (18)0.113 (3)0.083 (2)0.0460 (17)0.0105 (15)0.0174 (19)
O60.0733 (19)0.079 (2)0.0406 (15)0.0107 (16)0.0144 (13)0.0078 (14)
O70.078 (2)0.0454 (17)0.0676 (18)0.0107 (14)0.0248 (15)0.0090 (14)
O80.104 (2)0.0565 (18)0.0601 (18)0.0157 (16)0.0254 (17)0.0171 (15)
O1w0.0637 (19)0.085 (3)0.0547 (18)0.0283 (18)0.0079 (15)0.0131 (18)
N10.0441 (15)0.0366 (15)0.0299 (13)0.0161 (12)0.0013 (11)0.0057 (11)
N20.0512 (18)0.0500 (18)0.0290 (15)0.0216 (14)0.0009 (13)0.0033 (13)
N30.0436 (15)0.0380 (15)0.0290 (13)0.0160 (12)0.0034 (11)0.0030 (11)
N40.0504 (17)0.0532 (19)0.0312 (15)0.0209 (14)0.0100 (13)0.0013 (13)
N50.054 (2)0.062 (2)0.0448 (17)0.0233 (17)0.0010 (15)0.0197 (16)
N60.0477 (17)0.053 (2)0.0403 (17)0.0136 (15)0.0065 (13)0.0022 (15)
C10.0376 (17)0.0366 (18)0.0356 (17)0.0096 (14)0.0075 (13)0.0066 (14)
C20.0439 (19)0.042 (2)0.0408 (18)0.0151 (15)0.0015 (15)0.0013 (15)
C30.057 (2)0.039 (2)0.058 (2)0.0174 (17)0.0152 (18)0.0019 (17)
C40.058 (2)0.043 (2)0.061 (2)0.0108 (18)0.0139 (19)0.0199 (18)
C50.049 (2)0.056 (2)0.0390 (18)0.0114 (17)0.0059 (15)0.0164 (17)
C60.0374 (18)0.047 (2)0.0337 (17)0.0108 (15)0.0065 (14)0.0079 (15)
C70.0428 (18)0.0443 (19)0.0296 (16)0.0183 (15)0.0035 (13)0.0045 (14)
C80.071 (2)0.046 (2)0.0370 (18)0.0307 (18)0.0024 (17)0.0018 (15)
C90.0439 (18)0.0379 (18)0.0303 (16)0.0157 (15)0.0028 (13)0.0030 (13)
C100.054 (2)0.045 (2)0.0394 (19)0.0154 (17)0.0022 (16)0.0023 (16)
C110.065 (3)0.039 (2)0.055 (2)0.0111 (18)0.0071 (19)0.0027 (17)
C120.078 (3)0.044 (2)0.061 (2)0.025 (2)0.014 (2)0.0158 (19)
C130.071 (3)0.062 (3)0.0393 (19)0.036 (2)0.0031 (18)0.0140 (18)
C140.049 (2)0.046 (2)0.0330 (17)0.0224 (16)0.0010 (14)0.0049 (15)
C150.0434 (19)0.044 (2)0.0297 (16)0.0176 (15)0.0012 (14)0.0016 (14)
C160.052 (2)0.047 (2)0.0350 (18)0.0115 (16)0.0077 (15)0.0005 (15)
Geometric parameters (Å, º) top
Zn1—O12.246 (3)N4—H4N0.85 (1)
Zn1—O22.173 (3)C1—C21.386 (5)
Zn1—O32.195 (2)C1—C61.403 (4)
Zn1—O42.213 (3)C2—C31.368 (5)
Zn1—N11.997 (2)C2—H20.93
Zn1—N31.993 (3)C3—C41.394 (5)
O1—C81.424 (4)C3—H30.93
O1—H1O0.85 (1)C4—C51.380 (5)
O2—C161.424 (4)C4—H40.93
O2—H2O0.84 (1)C5—C61.380 (5)
O3—N51.263 (4)C5—H50.93
O4—N51.255 (4)C7—C81.489 (5)
O5—N51.221 (4)C8—H8A0.97
O6—N61.261 (4)C8—H8B0.97
O7—N61.224 (4)C9—C101.380 (5)
O8—N61.233 (4)C9—C141.401 (5)
O1w—H1W10.85 (1)C10—C111.376 (5)
O1w—H1W20.85 (1)C10—H100.93
N1—C71.316 (4)C11—C121.392 (6)
N1—C11.393 (4)C11—H110.93
N2—C71.346 (4)C12—C131.363 (6)
N2—C61.385 (5)C12—H120.93
N2—H2N0.85 (1)C13—C141.392 (5)
N3—C151.318 (4)C13—H130.93
N3—C91.398 (4)C15—C161.474 (5)
N4—C151.343 (4)C16—H16A0.97
N4—C141.376 (4)C16—H16B0.97
O1—Zn1—O2117.3 (1)C2—C3—C4122.1 (4)
O1—Zn1—O396.2 (1)C2—C3—H3119.0
O1—Zn1—O4154.1 (1)C4—C3—H3119.0
O1—Zn1—N176.2 (1)C5—C4—C3121.6 (3)
O1—Zn1—N385.3 (1)C5—C4—H4119.2
O2—Zn1—O3145.4 (1)C3—C4—H4119.2
O2—Zn1—O488.6 (1)C4—C5—C6116.4 (3)
O2—Zn1—N196.7 (1)C4—C5—H5121.8
O2—Zn1—N377.1 (1)C6—C5—H5121.8
O3—Zn1—O458.1 (1)C5—C6—N2132.6 (3)
O3—Zn1—N199.5 (1)C5—C6—C1122.2 (3)
O3—Zn1—N398.8 (1)N2—C6—C1105.2 (3)
O4—Zn1—N1103.1 (1)N1—C7—N2112.3 (3)
O4—Zn1—N3100.8 (1)N1—C7—C8122.5 (3)
N1—Zn1—N3155.2 (1)N2—C7—C8125.2 (3)
C8—O1—Zn1114.9 (2)O1—C8—C7107.1 (3)
C8—O1—H1O110 (4)O1—C8—H8A110.3
Zn1—O1—H1O108 (4)C7—C8—H8A110.3
C16—O2—Zn1115.8 (2)O1—C8—H8B110.3
C16—O2—H2O110 (3)C7—C8—H8B110.3
Zn1—O2—H2O128 (3)H8A—C8—H8B108.5
N5—O3—Zn193.0 (2)C10—C9—N3131.3 (3)
N5—O4—Zn192.4 (2)C10—C9—C14120.8 (3)
H1W1—O1w—H1W2110 (5)N3—C9—C14107.9 (3)
C7—N1—C1106.0 (3)C11—C10—C9117.5 (3)
C7—N1—Zn1119.0 (2)C11—C10—H10121.2
C1—N1—Zn1134.9 (2)C9—C10—H10121.2
C7—N2—C6107.8 (3)C10—C11—C12121.2 (4)
C7—N2—H2N125 (3)C10—C11—H11119.4
C6—N2—H2N127 (3)C12—C11—H11119.4
C15—N3—C9106.4 (3)C13—C12—C11122.3 (4)
C15—N3—Zn1117.5 (2)C13—C12—H12118.8
C9—N3—Zn1135.2 (2)C11—C12—H12118.8
C15—N4—C14108.2 (3)C12—C13—C14116.7 (4)
C15—N4—H4N124 (2)C12—C13—H13121.6
C14—N4—H4N128 (2)C14—C13—H13121.6
O5—N5—O4122.3 (4)N4—C14—C13132.9 (3)
O5—N5—O3121.3 (4)N4—C14—C9105.7 (3)
O4—N5—O3116.5 (3)C13—C14—C9121.4 (3)
O7—N6—O8120.4 (3)N3—C15—N4111.8 (3)
O7—N6—O6121.1 (3)N3—C15—C16122.1 (3)
O8—N6—O6118.5 (3)N4—C15—C16126.1 (3)
C2—C1—N1130.7 (3)O2—C16—C15106.3 (3)
C2—C1—C6120.6 (3)O2—C16—H16A110.5
N1—C1—C6108.7 (3)C15—C16—H16A110.5
C3—C2—C1117.1 (3)O2—C16—H16B110.5
C3—C2—H2121.4C15—C16—H16B110.5
C1—C2—H2121.4H16A—C16—H16B108.7
N3—Zn1—O1—C8158.5 (3)N1—C1—C2—C3178.0 (3)
N1—Zn1—O1—C84.8 (2)C6—C1—C2—C30.4 (5)
O2—Zn1—O1—C885.7 (3)C1—C2—C3—C41.4 (5)
O3—Zn1—O1—C8103.1 (2)C2—C3—C4—C50.9 (6)
O4—Zn1—O1—C896.4 (3)C3—C4—C5—C60.6 (5)
N3—Zn1—O2—C166.1 (2)C4—C5—C6—N2177.4 (3)
N1—Zn1—O2—C16161.7 (2)C4—C5—C6—C11.5 (5)
O3—Zn1—O2—C1680.7 (3)C7—N2—C6—C5179.5 (3)
O4—Zn1—O2—C1695.3 (2)C7—N2—C6—C10.4 (4)
O1—Zn1—O2—C1683.8 (3)C2—C1—C6—C51.0 (5)
N3—Zn1—O3—N596.53 (19)N1—C1—C6—C5179.8 (3)
N1—Zn1—O3—N5100.28 (19)C2—C1—C6—N2178.1 (3)
O2—Zn1—O3—N516.6 (3)N1—C1—C6—N20.6 (4)
O4—Zn1—O3—N50.76 (18)C1—N1—C7—N20.3 (4)
O1—Zn1—O3—N5177.30 (18)Zn1—N1—C7—N2177.2 (2)
N3—Zn1—O4—N593.0 (2)C1—N1—C7—C8178.4 (3)
N1—Zn1—O4—N594.0 (2)Zn1—N1—C7—C84.1 (4)
O2—Zn1—O4—N5169.5 (2)C6—N2—C7—N10.1 (4)
O3—Zn1—O4—N50.76 (18)C6—N2—C7—C8178.7 (3)
O1—Zn1—O4—N58.7 (3)Zn1—O1—C8—C74.0 (4)
N3—Zn1—N1—C738.4 (4)N1—C7—C8—O10.3 (5)
O2—Zn1—N1—C7111.9 (2)N2—C7—C8—O1178.2 (3)
O3—Zn1—N1—C798.7 (2)C15—N3—C9—C10178.9 (3)
O4—Zn1—N1—C7158.0 (2)Zn1—N3—C9—C109.7 (5)
O1—Zn1—N1—C74.6 (2)C15—N3—C9—C140.1 (3)
N3—Zn1—N1—C1138.2 (3)Zn1—N3—C9—C14169.1 (2)
O2—Zn1—N1—C164.7 (3)N3—C9—C10—C11177.5 (3)
O3—Zn1—N1—C184.7 (3)C14—C9—C10—C111.1 (5)
O4—Zn1—N1—C125.4 (3)C9—C10—C11—C120.1 (5)
O1—Zn1—N1—C1178.8 (3)C10—C11—C12—C130.9 (6)
N1—Zn1—N3—C1577.0 (3)C11—C12—C13—C140.9 (6)
O2—Zn1—N3—C150.8 (2)C15—N4—C14—C13177.4 (4)
O3—Zn1—N3—C15145.8 (2)C15—N4—C14—C90.2 (4)
O4—Zn1—N3—C1586.8 (2)C12—C13—C14—N4177.4 (4)
O1—Zn1—N3—C15118.6 (2)C12—C13—C14—C90.1 (5)
N1—Zn1—N3—C991.3 (4)C10—C9—C14—N4179.1 (3)
O2—Zn1—N3—C9169.1 (3)N3—C9—C14—N40.2 (4)
O3—Zn1—N3—C945.9 (3)C10—C9—C14—C131.1 (5)
O4—Zn1—N3—C9104.9 (3)N3—C9—C14—C13177.8 (3)
O1—Zn1—N3—C949.6 (3)C9—N3—C15—N40.0 (4)
Zn1—O4—N5—O5178.5 (3)Zn1—N3—C15—N4171.4 (2)
Zn1—O4—N5—O31.3 (3)C9—N3—C15—C16179.2 (3)
Zn1—O3—N5—O5178.5 (3)Zn1—N3—C15—C167.8 (4)
Zn1—O3—N5—O41.3 (3)C14—N4—C15—N30.1 (4)
C7—N1—C1—C2178.0 (3)C14—N4—C15—C16179.1 (3)
Zn1—N1—C1—C25.1 (5)Zn1—O2—C16—C1510.5 (3)
C7—N1—C1—C60.6 (3)N3—C15—C16—O212.1 (4)
Zn1—N1—C1—C6176.3 (2)N4—C15—C16—O2167.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O1w0.85 (1)1.80 (1)2.635 (4)172 (5)
O2—H2O···O6i0.84 (1)2.08 (2)2.877 (4)159 (4)
O1w—H1w1···O5ii0.85 (1)2.07 (2)2.908 (5)168 (5)
O1w—H1w2···O6iii0.85 (1)2.29 (3)3.038 (5)148 (5)
N2—H2n···O60.85 (1)2.14 (2)2.922 (4)154 (4)
N4—H4n···O7iv0.85 (1)2.14 (2)2.959 (4)163 (3)
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z; (iii) x+2, y+1, z+1; (iv) x, y, z+1.
 

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