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organic compounds
The ortho-disubstituted aromatic ring in the title compound, C27H32N2, is twisted by 76.1 (1)° with respect to the isopropyl-substituted ring and by 89.3 (1)° with respect to the methyl-substituted ring. The amino N atom is linked intramolecularly to the imino N by a hydrogen bond [NN = 2.686 (2) Å].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000492/bt6388sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000492/bt6388Isup2.hkl |
CCDC reference: 234863
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.179
- Data-to-parameter ratio = 19.3
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT242_ALERT_2_A Check Low U(eq) as Compared to Neighbors .... C10
Author Response: The C10 atom belongs to an isopropyl group. |
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.98 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.76 Ratio PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C7
Author Response: The C10 atom belongs to an isopropyl group. |
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C21
Author Response: The C10 atom belongs to an isopropyl group. |
1 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
2-[2-(2,6-Dimethylphenylamino)phenylmethyleneamino]-1,3-diisopropylbenzene top
Crystal data top
C27H32N2 | F(000) = 832 |
Mr = 384.55 | Dx = 1.079 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 854 reflections |
a = 12.013 (2) Å | θ = 2.7–23.1° |
b = 7.789 (1) Å | µ = 0.06 mm−1 |
c = 25.542 (3) Å | T = 293 K |
β = 97.802 (3)° | Block, yellow |
V = 2367.9 (5) Å3 | 0.49 × 0.48 × 0.43 mm |
Z = 4 |
Data collection top
Bruker SMART 1K area-detector diffractometer | 2681 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 27.1°, θmin = 1.6° |
φ and ω scans | h = −15→13 |
13131 measured reflections | k = −4→9 |
5184 independent reflections | l = −32→32 |
Refinement top
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.179 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0863P)2 + 0.2352P] where P = (Fo2 + 2Fc2)/3 |
5184 reflections | (Δ/σ)max = 0.001 |
268 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1 | 0.4781 (1) | 0.6477 (2) | 0.6552 (1) | 0.052 (1) | |
N2 | 0.3146 (1) | 0.5855 (2) | 0.5748 (1) | 0.066 (1) | |
C1 | 0.5491 (1) | 0.7591 (2) | 0.6886 (1) | 0.054 (1) | |
C2 | 0.6407 (2) | 0.8332 (3) | 0.6685 (1) | 0.066 (1) | |
C3 | 0.7042 (2) | 0.9517 (3) | 0.6998 (1) | 0.091 (1) | |
C4 | 0.6784 (2) | 0.9962 (4) | 0.7486 (1) | 0.108 (1) | |
C5 | 0.5885 (2) | 0.9226 (4) | 0.7673 (1) | 0.102 (1) | |
C6 | 0.5215 (2) | 0.8032 (3) | 0.7381 (1) | 0.071 (1) | |
C7 | 0.6672 (2) | 0.7854 (3) | 0.6144 (1) | 0.084 (1) | |
C8 | 0.6124 (3) | 0.9041 (5) | 0.5722 (1) | 0.144 (1) | |
C9 | 0.7913 (2) | 0.7689 (5) | 0.6109 (1) | 0.141 (1) | |
C10 | 0.4185 (2) | 0.7298 (4) | 0.7589 (1) | 0.089 (1) | |
C11 | 0.3348 (3) | 0.8677 (6) | 0.7684 (2) | 0.170 (2) | |
C12 | 0.4487 (3) | 0.6200 (7) | 0.8064 (2) | 0.196 (2) | |
C13 | 0.4804 (1) | 0.4868 (2) | 0.6621 (1) | 0.052 (1) | |
C14 | 0.4076 (1) | 0.3659 (2) | 0.6313 (1) | 0.049 (1) | |
C15 | 0.4159 (2) | 0.1926 (2) | 0.6446 (1) | 0.067 (1) | |
C16 | 0.3477 (2) | 0.0718 (3) | 0.6179 (1) | 0.080 (1) | |
C17 | 0.2691 (2) | 0.1221 (3) | 0.5766 (1) | 0.077 (1) | |
C18 | 0.2580 (2) | 0.2903 (2) | 0.5622 (1) | 0.066 (1) | |
C19 | 0.3259 (1) | 0.4164 (2) | 0.5890 (1) | 0.051 (1) | |
C20 | 0.2298 (2) | 0.6483 (2) | 0.5350 (1) | 0.058 (1) | |
C21 | 0.1259 (2) | 0.6937 (3) | 0.5492 (1) | 0.071 (1) | |
C22 | 0.0454 (2) | 0.7570 (3) | 0.5105 (1) | 0.088 (1) | |
C23 | 0.0658 (2) | 0.7726 (3) | 0.4600 (1) | 0.095 (1) | |
C24 | 0.1680 (2) | 0.7291 (3) | 0.4462 (1) | 0.093 (1) | |
C25 | 0.2536 (2) | 0.6664 (3) | 0.4836 (1) | 0.072 (1) | |
C26 | 0.1023 (3) | 0.6751 (4) | 0.6050 (1) | 0.118 (1) | |
C27 | 0.3675 (2) | 0.6233 (4) | 0.4697 (1) | 0.110 (1) | |
H2 | 0.360 (2) | 0.660 (3) | 0.5933 (9) | 0.085 (7)* | |
H3 | 0.7658 | 1.0024 | 0.6875 | 0.109* | |
H4 | 0.7222 | 1.0765 | 0.7690 | 0.130* | |
H5 | 0.5720 | 0.9536 | 0.8005 | 0.122* | |
H7 | 0.6344 | 0.6716 | 0.6065 | 0.100* | |
H8A | 0.6327 | 0.8705 | 0.5386 | 0.216* | |
H8B | 0.6371 | 1.0196 | 0.5801 | 0.216* | |
H8C | 0.5323 | 0.8981 | 0.5710 | 0.216* | |
H9A | 0.8244 | 0.6882 | 0.6368 | 0.211* | |
H9B | 0.8268 | 0.8787 | 0.6172 | 0.211* | |
H9C | 0.8015 | 0.7293 | 0.5762 | 0.211* | |
H10 | 0.3809 | 0.6551 | 0.7311 | 0.107* | |
H11a | 0.3077 | 0.9231 | 0.7355 | 0.254* | |
H11b | 0.3708 | 0.9509 | 0.7928 | 0.254* | |
H11c | 0.2730 | 0.8167 | 0.7828 | 0.254* | |
H12a | 0.5005 | 0.5327 | 0.7986 | 0.295* | |
H12b | 0.3822 | 0.5671 | 0.8159 | 0.295* | |
H12c | 0.4831 | 0.6893 | 0.8352 | 0.295* | |
H13 | 0.5328 | 0.4434 | 0.6890 | 0.062* | |
H15 | 0.4693 | 0.1580 | 0.6724 | 0.081* | |
H16 | 0.3545 | −0.0432 | 0.6276 | 0.096* | |
H17 | 0.2228 | 0.0403 | 0.5582 | 0.093* | |
H18 | 0.2043 | 0.3216 | 0.5341 | 0.079* | |
H22 | −0.0242 | 0.7896 | 0.5193 | 0.105* | |
H23 | 0.0096 | 0.8134 | 0.4343 | 0.114* | |
H24 | 0.1807 | 0.7415 | 0.4112 | 0.112* | |
H26a | 0.1610 | 0.7296 | 0.6284 | 0.177* | |
H26b | 0.0991 | 0.5555 | 0.6137 | 0.177* | |
H26c | 0.0317 | 0.7284 | 0.6086 | 0.177* | |
H27a | 0.3675 | 0.6374 | 0.4323 | 0.164* | |
H27b | 0.3856 | 0.5065 | 0.4793 | 0.164* | |
H27c | 0.4224 | 0.6985 | 0.4884 | 0.164* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.047 (1) | 0.048 (1) | 0.058 (1) | −0.003 (1) | −0.004 (1) | 0.001 (1) |
N2 | 0.065 (1) | 0.043 (1) | 0.079 (1) | −0.005 (1) | −0.025 (1) | 0.005 (1) |
C1 | 0.043 (1) | 0.052 (1) | 0.062 (1) | −0.001 (1) | −0.009 (1) | −0.003 (1) |
C2 | 0.049 (1) | 0.059 (1) | 0.088 (2) | −0.006 (1) | −0.001 (1) | 0.001 (1) |
C3 | 0.059 (1) | 0.081 (2) | 0.129 (2) | −0.019 (1) | −0.004 (1) | −0.006 (2) |
C4 | 0.086 (2) | 0.106 (2) | 0.124 (2) | −0.026 (2) | −0.020 (2) | −0.043 (2) |
C5 | 0.089 (2) | 0.119 (2) | 0.091 (2) | −0.016 (2) | −0.006 (1) | −0.041 (2) |
C6 | 0.060 (1) | 0.083 (1) | 0.066 (1) | −0.007 (1) | −0.005 (1) | −0.014 (1) |
C7 | 0.069 (2) | 0.088 (2) | 0.098 (2) | −0.011 (1) | 0.025 (1) | 0.005 (1) |
C8 | 0.126 (3) | 0.201 (4) | 0.107 (2) | 0.032 (3) | 0.022 (2) | 0.030 (2) |
C9 | 0.090 (2) | 0.189 (4) | 0.149 (3) | 0.032 (2) | 0.038 (2) | 0.017 (3) |
C10 | 0.082 (2) | 0.119 (2) | 0.068 (1) | −0.011 (2) | 0.015 (1) | −0.018 (1) |
C11 | 0.118 (3) | 0.184 (4) | 0.220 (4) | 0.013 (3) | 0.074 (3) | −0.028 (3) |
C12 | 0.139 (3) | 0.300 (6) | 0.147 (3) | −0.034 (4) | 0.011 (3) | 0.114 (4) |
C13 | 0.044 (1) | 0.054 (1) | 0.057 (1) | 0.005 (1) | 0.000 (1) | 0.003 (1) |
C14 | 0.043 (1) | 0.045 (1) | 0.059 (1) | 0.003 (1) | 0.004 (1) | 0.002 (1) |
C15 | 0.062 (1) | 0.051 (1) | 0.086 (1) | 0.006 (1) | −0.002 (1) | 0.007 (1) |
C16 | 0.083 (2) | 0.041 (1) | 0.113 (2) | 0.000 (1) | 0.000 (1) | 0.003 (1) |
C17 | 0.073 (1) | 0.047 (1) | 0.107 (2) | −0.010 (1) | −0.005 (1) | −0.007 (1) |
C18 | 0.058 (1) | 0.052 (1) | 0.083 (1) | −0.007 (1) | −0.010 (1) | −0.003 (1) |
C19 | 0.047 (1) | 0.043 (1) | 0.063 (1) | −0.002 (1) | 0.003 (1) | −0.001 (1) |
C20 | 0.054 (1) | 0.041 (1) | 0.073 (1) | −0.003 (1) | −0.015 (1) | 0.003 (1) |
C21 | 0.058 (1) | 0.067 (1) | 0.084 (2) | −0.007 (1) | −0.004 (1) | 0.004 (1) |
C22 | 0.053 (1) | 0.094 (2) | 0.111 (2) | 0.004 (1) | −0.008 (1) | 0.014 (2) |
C23 | 0.072 (2) | 0.099 (2) | 0.104 (2) | 0.009 (1) | −0.027 (2) | 0.020 (2) |
C24 | 0.101 (2) | 0.096 (2) | 0.076 (2) | 0.009 (2) | −0.009 (1) | 0.015 (1) |
C25 | 0.075 (1) | 0.063 (1) | 0.074 (1) | 0.008 (1) | −0.005 (1) | 0.003 (1) |
C26 | 0.097 (2) | 0.155 (3) | 0.106 (2) | 0.001 (2) | 0.024 (2) | 0.014 (2) |
C27 | 0.100 (2) | 0.119 (2) | 0.111 (2) | 0.032 (2) | 0.023 (2) | 0.004 (2) |
Geometric parameters (Å, º) top
N1—C1 | 1.418 (2) | C3—H3 | 0.93 |
N1—C13 | 1.265 (2) | C4—H4 | 0.93 |
N2—C19 | 1.368 (2) | C5—H5 | 0.93 |
N2—C20 | 1.424 (2) | C7—H7 | 0.98 |
C1—C6 | 1.393 (3) | C8—H8a | 0.96 |
C1—C2 | 1.400 (3) | C8—H8b | 0.96 |
C2—C3 | 1.381 (3) | C8—H8c | 0.96 |
C2—C7 | 1.507 (3) | C9—H9a | 0.96 |
C3—C4 | 1.369 (4) | C9—H9b | 0.96 |
C4—C5 | 1.365 (4) | C9—H9c | 0.96 |
C5—C6 | 1.381 (3) | C10—H10 | 0.98 |
C6—C10 | 1.523 (3) | C11—H11a | 0.96 |
C7—C8 | 1.502 (4) | C11—H11b | 0.96 |
C7—C9 | 1.511 (4) | C11—H11c | 0.96 |
C10—C12 | 1.487 (4) | C12—H12a | 0.96 |
C10—C11 | 1.513 (4) | C12—H12b | 0.96 |
C13—C14 | 1.444 (2) | C12—H12c | 0.96 |
C14—C15 | 1.392 (2) | C13—H13 | 0.93 |
C14—C19 | 1.413 (2) | C15—H15 | 0.93 |
C15—C16 | 1.367 (3) | C16—H16 | 0.93 |
C16—C17 | 1.374 (3) | C17—H17 | 0.93 |
C17—C18 | 1.362 (3) | C18—H18 | 0.93 |
C18—C19 | 1.396 (2) | C22—H22 | 0.93 |
C20—C25 | 1.390 (3) | C23—H23 | 0.93 |
C20—C21 | 1.391 (3) | C24—H24 | 0.93 |
C21—C22 | 1.378 (3) | C26—H26a | 0.96 |
C21—C26 | 1.496 (3) | C26—H26b | 0.96 |
C22—C23 | 1.352 (4) | C26—H26c | 0.96 |
C23—C24 | 1.366 (4) | C27—H27a | 0.96 |
C24—C25 | 1.394 (3) | C27—H27b | 0.96 |
C25—C27 | 1.498 (3) | C27—H27c | 0.96 |
N2—H2 | 0.89 (2) | ||
C1—N1—C13 | 121.4 (2) | C7—C8—H8b | 109.5 |
C19—N2—C20 | 123.8 (2) | H8a—C8—H8b | 109.5 |
C2—C1—C6 | 121.8 (2) | C7—C8—H8c | 109.5 |
C6—C1—N1 | 120.0 (2) | H8a—C8—H8c | 109.5 |
C2—C1—N1 | 118.0 (2) | H8b—C8—H8c | 109.5 |
C1—C2—C3 | 117.6 (2) | C7—C9—H9a | 109.5 |
C1—C2—C7 | 120.6 (2) | C7—C9—H9b | 109.5 |
C3—C2—C7 | 121.8 (2) | H9a—C9—H9b | 109.5 |
C2—C3—C4 | 121.4 (2) | C7—C9—H9c | 109.5 |
C3—C4—C5 | 119.9 (2) | H9a—C9—H9c | 109.5 |
C4—C5—C6 | 121.7 (2) | H9b—C9—H9c | 109.5 |
C1—C6—C5 | 117.6 (2) | C12—C10—H10 | 106.6 |
C1—C6—C10 | 122.0 (2) | C11—C10—H10 | 106.6 |
C5—C6—C10 | 120.4 (2) | C6—C10—H10 | 106.6 |
C2—C7—C8 | 112.3 (2) | C10—C11—H11a | 109.5 |
C2—C7—C9 | 114.2 (2) | C10—C11—H11b | 109.5 |
C8—C7—C9 | 110.5 (2) | H11a—C11—H11b | 109.5 |
C6—C10—C11 | 112.2 (2) | C10—C11—H11c | 109.5 |
C6—C10—C12 | 112.4 (2) | H11a—C11—H11c | 109.5 |
C11—C10—C12 | 111.9 (3) | H11b—C11—H11c | 109.5 |
N1—C13—C14 | 124.7 (2) | C10—C12—H12a | 109.5 |
C13—C14—C15 | 118.9 (2) | C10—C12—H12b | 109.5 |
C13—C14—C19 | 122.8 (2) | H12a—C12—H12b | 109.5 |
C15—C14—C19 | 118.4 (2) | C10—C12—H12c | 109.5 |
C14—C15—C16 | 121.9 (2) | H12a—C12—H12c | 109.5 |
C15—C16—C17 | 119.3 (2) | H12b—C12—H12c | 109.5 |
C16—C17—C18 | 120.9 (2) | N1—C13—H13 | 117.6 |
C17—C18—C19 | 121.0 (2) | C14—C13—H13 | 117.6 |
N2—C19—C14 | 120.3 (2) | C16—C15—H15 | 119.1 |
N2—C19—C18 | 121.1 (2) | C14—C15—H15 | 119.1 |
C18—C19—C14 | 118.6 (2) | C15—C16—H16 | 120.4 |
C21—C20—C25 | 121.9 (2) | C17—C16—H16 | 120.4 |
C25—C20—N2 | 119.3 (2) | C18—C17—H17 | 119.6 |
C21—C20—N2 | 118.8 (2) | C16—C17—H17 | 119.6 |
C20—C21—C22 | 118.1 (2) | C17—C18—H18 | 119.5 |
C20—C21—C26 | 121.1 (2) | C19—C18—H18 | 119.5 |
C22—C21—C26 | 120.8 (2) | C23—C22—H22 | 119.5 |
C21—C22—C23 | 121.1 (2) | C21—C22—H22 | 119.5 |
C22—C23—C24 | 120.7 (2) | C22—C23—H23 | 119.6 |
C23—C24—C25 | 121.0 (2) | C24—C23—H23 | 119.6 |
C20—C25—C24 | 117.2 (2) | C23—C24—H24 | 119.5 |
C20—C25—C27 | 120.9 (2) | C25—C24—H24 | 119.5 |
C24—C25—C27 | 121.9 (2) | C21—C26—H26a | 109.5 |
C19—N2—H2 | 117 (1) | C21—C26—H26b | 109.5 |
C20—N2—H2 | 119 (1) | H26a—C26—H26b | 109.5 |
C4—C3—H3 | 119.3 | C21—C26—H26c | 109.5 |
C2—C3—H3 | 119.3 | H26a—C26—H26c | 109.5 |
C5—C4—H4 | 120.0 | H26b—C26—H26c | 109.5 |
C3—C4—H4 | 120.0 | C25—C27—H27a | 109.5 |
C4—C5—H5 | 119.1 | C25—C27—H27b | 109.5 |
C6—C5—H5 | 119.1 | H27a—C27—H27b | 109.5 |
C8—C7—H7 | 106.5 | C25—C27—H27c | 109.5 |
C2—C7—H7 | 106.5 | H27a—C27—H27c | 109.5 |
C9—C7—H7 | 106.5 | H27b—C27—H27c | 109.5 |
C7—C8—H8a | 109.5 | ||
C13—N1—C1—C6 | −79.0 (2) | C13—C14—C15—C16 | 178.5 (2) |
C13—N1—C1—C2 | 106.3 (2) | C14—C15—C16—C17 | 0.4 (3) |
C6—C1—C2—C3 | 0.5 (3) | C15—C16—C17—C18 | −0.4 (4) |
N1—C1—C2—C3 | 175.1 (2) | C16—C17—C18—C19 | −0.1 (3) |
C6—C1—C2—C7 | −178.8 (2) | C20—N2—C19—C18 | 4.5 (3) |
N1—C1—C2—C7 | −4.3 (3) | C20—N2—C19—C14 | −175.7 (2) |
C1—C2—C3—C4 | −0.3 (3) | C17—C18—C19—N2 | −179.7 (2) |
C7—C2—C3—C4 | 179.0 (2) | C17—C18—C19—C14 | 0.5 (3) |
C2—C3—C4—C5 | 0.2 (4) | C15—C14—C19—N2 | 179.8 (2) |
C3—C4—C5—C6 | −0.2 (5) | C13—C14—C19—N2 | 1.4 (3) |
C4—C5—C6—C1 | 0.3 (4) | C15—C14—C19—C18 | −0.4 (3) |
C4—C5—C6—C10 | −177.1 (3) | C13—C14—C19—C18 | −178.8 (2) |
C2—C1—C6—C5 | −0.5 (3) | C19—N2—C20—C25 | −94.0 (2) |
N1—C1—C6—C5 | −175.0 (2) | C19—N2—C20—C21 | 87.5 (2) |
C2—C1—C6—C10 | 176.9 (2) | C25—C20—C21—C22 | 0.4 (3) |
N1—C1—C6—C10 | 2.4 (3) | N2—C20—C21—C22 | 178.9 (2) |
C3—C2—C7—C8 | −86.9 (3) | C25—C20—C21—C26 | −179.3 (2) |
C1—C2—C7—C8 | 92.4 (3) | N2—C20—C21—C26 | −0.8 (3) |
C3—C2—C7—C9 | 39.8 (3) | C20—C21—C22—C23 | 0.9 (3) |
C1—C2—C7—C9 | −140.9 (2) | C26—C21—C22—C23 | −179.4 (3) |
C5—C6—C10—C12 | −67.5 (4) | C21—C22—C23—C24 | −1.4 (4) |
C1—C6—C10—C12 | 115.2 (3) | C22—C23—C24—C25 | 0.5 (4) |
C5—C6—C10—C11 | 59.6 (3) | C21—C20—C25—C24 | −1.2 (3) |
C1—C6—C10—C11 | −117.7 (3) | N2—C20—C25—C24 | −179.7 (2) |
C1—N1—C13—C14 | 177.1 (2) | C21—C20—C25—C27 | 177.5 (2) |
N1—C13—C14—C15 | −177.4 (2) | N2—C20—C25—C27 | −1.0 (3) |
N1—C13—C14—C19 | 1.0 (3) | C23—C24—C25—C20 | 0.8 (4) |
C19—C14—C15—C16 | 0.0 (3) | C23—C24—C25—C27 | −177.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···N1 | 0.89 (2) | 1.98 (2) | 2.686 (2) | 136 (2) |
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