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The structure of the title compound, C2H10N22+·2C7H4NO4-·2H2O, comprises interdigitated two-dimensional hydrogen-bonded networks derived from a repeat unit that contains the bisammonium, two benzoates and two water molecules.
Supporting information
CCDC reference: 217618
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.150
- Data-to-parameter ratio = 11.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
1:2 molar amounts of ethane-1,2-diamine and 4-nitrobenzoic acid were refluxed in ethanol for 20 min. Total evaporation of the solvent gave colourless needles (m.p. 465 K).
All H atoms on the amines were initially located in difference syntheses but were then included in the refinement (along with all other H atoms) at calculated positions as riding models, with N—H set to 0.89 Å and C—H set to 0.97 (CH2) and 0.93 Å (Ar—H), while the isotropic displacement parameters were set equal to 1.25Ueq of the preceeding normal atom. All water H atoms were located on difference syntheses and both positional and isotropic displacement parameters were refined.
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
Ethane-1,2-diammonium bis(4-nitrobenzoate) bishydrate
top
Crystal data top
C2H10N22+·2C7H4NO4−·2H2O | F(000) = 904 |
Mr = 430.38 | Dx = 1.486 Mg m−3 |
Triclinic, P1 | Melting point: 465 K K |
a = 12.213 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 22.317 (2) Å | Cell parameters from 25 reflections |
c = 7.091 (5) Å | θ = 13.0–19.2° |
α = 89.47 (2)° | µ = 0.13 mm−1 |
β = 89.17 (2)° | T = 298 K |
γ = 84.72 (8)° | Needle, colourless |
V = 1924.2 (14) Å3 | 0.40 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Rigaku AFC7-R diffractometer | Rint = 0.000 |
Radiation source: Rigaku rotating anode | θmax = 25.4°, θmin = 2.6° |
Graphite monochromator | h = 0→14 |
ω–2θ scans | k = −26→26 |
6810 measured reflections | l = −8→8 |
6810 independent reflections | 3 standard reflections every 150 reflections |
3360 reflections with I > 2σ(I) | intensity decay: 0.4% |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0767P)2] where P = (Fo2 + 2Fc2)/3 |
6810 reflections | (Δ/σ)max < 0.001 |
577 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Crystal data top
C2H10N22+·2C7H4NO4−·2H2O | γ = 84.72 (8)° |
Mr = 430.38 | V = 1924.2 (14) Å3 |
Triclinic, P1 | Z = 4 |
a = 12.213 (2) Å | Mo Kα radiation |
b = 22.317 (2) Å | µ = 0.13 mm−1 |
c = 7.091 (5) Å | T = 298 K |
α = 89.47 (2)° | 0.40 × 0.20 × 0.10 mm |
β = 89.17 (2)° | |
Data collection top
Rigaku AFC7-R diffractometer | Rint = 0.000 |
6810 measured reflections | 3 standard reflections every 150 reflections |
6810 independent reflections | intensity decay: 0.4% |
3360 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.21 e Å−3 |
6810 reflections | Δρmin = −0.30 e Å−3 |
577 parameters | |
Special details top
Experimental. The scan width was (1.37 + 0.35tanθ)° with an ω scan speed of 0° per minute (up to 5 scans to achieve I/σ(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1A | 0.23216 (19) | 0.54109 (10) | 0.5570 (3) | 0.0426 (6) | |
H11A | 0.2902 | 0.5203 | 0.6083 | 0.053* | |
H12A | 0.1824 | 0.5514 | 0.6466 | 0.053* | |
H13A | 0.2532 | 0.5741 | 0.5013 | 0.053* | |
C2A | 0.1823 (3) | 0.50264 (14) | 0.4122 (4) | 0.0508 (8) | |
H21A | 0.1451 | 0.4717 | 0.4773 | 0.064* | |
H22A | 0.1275 | 0.5276 | 0.3421 | 0.064* | |
C3A | 0.2647 (3) | 0.47324 (13) | 0.2766 (4) | 0.0501 (8) | |
H31A | 0.3260 | 0.4539 | 0.3469 | 0.063* | |
H32A | 0.2312 | 0.4422 | 0.2094 | 0.063* | |
N4A | 0.30677 (19) | 0.51532 (10) | 0.1391 (3) | 0.0419 (6) | |
H41A | 0.2506 | 0.5360 | 0.0825 | 0.052* | |
H42A | 0.3485 | 0.4948 | 0.0533 | 0.052* | |
H43A | 0.3467 | 0.5406 | 0.1982 | 0.052* | |
C1B | 0.5510 (2) | 0.30216 (12) | 0.6369 (3) | 0.0332 (6) | |
C11B | 0.6082 (2) | 0.35913 (13) | 0.6421 (4) | 0.0399 (7) | |
O10B | 0.55370 (17) | 0.40763 (10) | 0.6822 (4) | 0.0641 (7) | |
O11B | 0.70769 (17) | 0.35512 (9) | 0.6090 (4) | 0.0650 (7) | |
C2B | 0.4414 (2) | 0.30245 (12) | 0.5804 (4) | 0.0375 (7) | |
H2B | 0.4017 | 0.3387 | 0.5498 | 0.047* | |
C3B | 0.3915 (2) | 0.24917 (13) | 0.5696 (4) | 0.0381 (7) | |
H3B | 0.3195 | 0.2490 | 0.5286 | 0.048* | |
C4B | 0.4518 (2) | 0.19635 (12) | 0.6215 (4) | 0.0384 (7) | |
N41B | 0.3984 (2) | 0.13999 (12) | 0.6152 (4) | 0.0513 (7) | |
O41B | 0.3031 (2) | 0.14151 (11) | 0.5588 (4) | 0.0746 (7) | |
O42B | 0.4509 (2) | 0.09368 (11) | 0.6659 (4) | 0.0750 (7) | |
C5B | 0.5598 (2) | 0.19450 (13) | 0.6796 (4) | 0.0412 (7) | |
H5B | 0.5982 | 0.1583 | 0.7145 | 0.051* | |
C6B | 0.6094 (2) | 0.24795 (12) | 0.6847 (4) | 0.0370 (7) | |
H6B | 0.6825 | 0.2475 | 0.7205 | 0.046* | |
C1C | 0.0584 (2) | 0.31712 (12) | 0.8603 (4) | 0.0349 (6) | |
C11C | 0.1147 (2) | 0.37438 (13) | 0.8531 (4) | 0.0427 (7) | |
O10C | 0.20968 (17) | 0.37066 (10) | 0.7932 (4) | 0.0689 (7) | |
O11C | 0.06181 (19) | 0.42206 (10) | 0.9060 (4) | 0.0724 (8) | |
C2C | 0.1165 (2) | 0.26292 (12) | 0.8119 (4) | 0.0360 (6) | |
H2C | 0.1896 | 0.2627 | 0.7732 | 0.045* | |
C3C | 0.0684 (2) | 0.20914 (12) | 0.8196 (4) | 0.0381 (7) | |
H3C | 0.1077 | 0.1730 | 0.7866 | 0.048* | |
C4C | −0.0391 (2) | 0.21130 (12) | 0.8777 (4) | 0.0357 (6) | |
N41C | −0.0913 (2) | 0.15434 (11) | 0.8885 (3) | 0.0487 (6) | |
O41C | −0.0347 (2) | 0.10731 (10) | 0.8572 (4) | 0.0763 (8) | |
O42C | −0.1883 (2) | 0.15646 (10) | 0.9308 (4) | 0.0708 (7) | |
C5C | −0.1000 (2) | 0.26391 (12) | 0.9253 (4) | 0.0380 (7) | |
H5C | −0.1733 | 0.2637 | 0.9627 | 0.047* | |
C6C | −0.0508 (2) | 0.31696 (12) | 0.9169 (4) | 0.0372 (7) | |
H6C | −0.0909 | 0.3529 | 0.9493 | 0.047* | |
N1D | 0.31709 (19) | 0.01744 (10) | 0.3166 (3) | 0.0422 (6) | |
H11D | 0.3579 | −0.0031 | 0.4026 | 0.053* | |
H12D | 0.2586 | 0.0368 | 0.3726 | 0.053* | |
H13D | 0.3568 | 0.0440 | 0.2595 | 0.053* | |
C2D | 0.2798 (3) | −0.02539 (12) | 0.1725 (4) | 0.0461 (7) | |
H21D | 0.2485 | −0.0582 | 0.2382 | 0.058* | |
H22D | 0.3436 | −0.0424 | 0.1015 | 0.058* | |
C3D | 0.1956 (2) | 0.00314 (13) | 0.0350 (4) | 0.0463 (8) | |
H31D | 0.1620 | −0.0285 | −0.0295 | 0.058* | |
H32D | 0.1382 | 0.0266 | 0.1054 | 0.058* | |
N4D | 0.24285 (19) | 0.04236 (10) | −0.1063 (3) | 0.0426 (6) | |
H41D | 0.2636 | 0.0749 | −0.0500 | 0.053* | |
H42D | 0.1926 | 0.0535 | −0.1925 | 0.053* | |
H43D | 0.3009 | 0.0225 | −0.1619 | 0.053* | |
C1E | 0.4494 (2) | 0.20569 (12) | 0.1205 (3) | 0.0336 (6) | |
C11E | 0.3959 (2) | 0.14704 (12) | 0.1124 (4) | 0.0374 (7) | |
O10E | 0.30232 (16) | 0.14802 (9) | 0.0421 (3) | 0.0519 (5) | |
O11E | 0.44859 (16) | 0.10078 (9) | 0.1802 (3) | 0.0554 (6) | |
C2E | 0.3873 (2) | 0.25904 (12) | 0.0739 (4) | 0.0354 (6) | |
H2E | 0.3147 | 0.2581 | 0.0373 | 0.044* | |
C3E | 0.4326 (2) | 0.31335 (12) | 0.0816 (4) | 0.0393 (7) | |
H3E | 0.3910 | 0.3492 | 0.0526 | 0.049* | |
C4E | 0.5415 (2) | 0.31327 (12) | 0.1335 (4) | 0.0374 (7) | |
N41E | 0.5910 (2) | 0.37068 (12) | 0.1401 (3) | 0.0519 (7) | |
O41E | 0.5309 (2) | 0.41736 (11) | 0.1533 (4) | 0.0830 (8) | |
O42E | 0.6909 (2) | 0.36982 (11) | 0.1331 (4) | 0.0767 (8) | |
C5E | 0.6062 (2) | 0.26158 (13) | 0.1794 (4) | 0.0387 (7) | |
H5E | 0.6792 | 0.2630 | 0.2133 | 0.048* | |
C6E | 0.5595 (2) | 0.20742 (13) | 0.1738 (4) | 0.0380 (7) | |
H6E | 0.6013 | 0.1719 | 0.2055 | 0.047* | |
C1F | 0.9342 (2) | 0.17594 (12) | 0.3766 (4) | 0.0343 (6) | |
C11F | 0.8784 (2) | 0.11876 (13) | 0.3850 (4) | 0.0401 (7) | |
O10F | 0.77933 (17) | 0.12319 (10) | 0.4250 (4) | 0.0663 (7) | |
O11F | 0.93598 (17) | 0.07002 (9) | 0.3498 (3) | 0.0532 (6) | |
C2F | 0.8773 (2) | 0.23024 (12) | 0.4279 (4) | 0.0373 (7) | |
H2F | 0.8041 | 0.2306 | 0.4663 | 0.047* | |
C3F | 0.9259 (2) | 0.28348 (12) | 0.4235 (4) | 0.0402 (7) | |
H3F | 0.8871 | 0.3195 | 0.4591 | 0.050* | |
C4F | 1.0336 (2) | 0.28150 (12) | 0.3647 (4) | 0.0366 (7) | |
N41F | 1.0868 (2) | 0.33846 (11) | 0.3596 (4) | 0.0495 (7) | |
O41F | 1.0315 (2) | 0.38479 (10) | 0.4007 (4) | 0.0734 (7) | |
O42F | 1.1829 (2) | 0.33641 (11) | 0.3158 (4) | 0.0740 (7) | |
C5F | 1.0935 (2) | 0.22884 (12) | 0.3109 (4) | 0.0355 (6) | |
H5F | 1.1663 | 0.2290 | 0.2711 | 0.044* | |
C6F | 1.0430 (2) | 0.17582 (12) | 0.3172 (4) | 0.0358 (6) | |
H6F | 1.0822 | 0.1399 | 0.2814 | 0.045* | |
O1W | 0.11838 (18) | 0.53425 (11) | 0.8988 (3) | 0.0493 (6) | |
H11 | 0.062 (3) | 0.5558 (16) | 0.945 (5) | 0.077 (12)* | |
H12 | 0.106 (2) | 0.4949 (16) | 0.884 (4) | 0.059 (10)* | |
O2W | 0.35040 (19) | 0.45444 (9) | 0.7890 (3) | 0.0484 (6) | |
H21 | 0.297 (3) | 0.4269 (19) | 0.780 (6) | 0.102 (15)* | |
H22 | 0.410 (3) | 0.4349 (15) | 0.754 (5) | 0.068 (11)* | |
O3W | 0.12918 (18) | 0.03580 (11) | 0.5424 (3) | 0.0472 (5) | |
H31 | 0.074 (3) | 0.0501 (14) | 0.492 (4) | 0.056 (11)* | |
H32 | 0.109 (2) | −0.0040 (15) | 0.577 (4) | 0.061 (10)* | |
O4W | 0.63636 (19) | 0.04438 (9) | 0.3369 (3) | 0.0476 (5) | |
H41 | 0.578 (3) | 0.0638 (16) | 0.289 (5) | 0.078 (13)* | |
H42 | 0.689 (3) | 0.0755 (17) | 0.368 (5) | 0.086 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0460 (14) | 0.0391 (14) | 0.0435 (14) | −0.0098 (11) | 0.0137 (11) | −0.0021 (11) |
C2A | 0.0536 (19) | 0.0520 (19) | 0.0498 (19) | −0.0220 (16) | 0.0105 (15) | −0.0002 (15) |
C3A | 0.065 (2) | 0.0394 (17) | 0.0475 (19) | −0.0181 (15) | 0.0135 (16) | −0.0031 (14) |
N4A | 0.0467 (14) | 0.0382 (14) | 0.0421 (14) | −0.0112 (11) | 0.0100 (11) | −0.0047 (10) |
C1B | 0.0358 (15) | 0.0393 (16) | 0.0248 (14) | −0.0058 (13) | 0.0091 (11) | −0.0026 (11) |
C11B | 0.0380 (17) | 0.0429 (18) | 0.0388 (17) | −0.0056 (14) | 0.0093 (13) | −0.0005 (13) |
O10B | 0.0438 (13) | 0.0436 (13) | 0.1059 (19) | −0.0110 (10) | 0.0189 (12) | −0.0218 (12) |
O11B | 0.0423 (13) | 0.0437 (13) | 0.109 (2) | −0.0095 (10) | 0.0236 (12) | 0.0093 (12) |
C2B | 0.0405 (17) | 0.0390 (16) | 0.0325 (15) | −0.0016 (13) | 0.0063 (12) | −0.0027 (12) |
C3B | 0.0348 (15) | 0.0490 (18) | 0.0315 (15) | −0.0095 (14) | 0.0031 (12) | −0.0086 (13) |
C4B | 0.0458 (18) | 0.0439 (17) | 0.0276 (15) | −0.0158 (14) | 0.0083 (13) | −0.0042 (12) |
N41B | 0.0610 (19) | 0.0481 (17) | 0.0475 (16) | −0.0218 (15) | 0.0128 (13) | −0.0073 (13) |
O41B | 0.0642 (17) | 0.0748 (17) | 0.0904 (19) | −0.0353 (14) | −0.0017 (14) | −0.0126 (14) |
O42B | 0.0865 (19) | 0.0475 (15) | 0.093 (2) | −0.0189 (14) | 0.0127 (15) | 0.0059 (13) |
C5B | 0.0488 (18) | 0.0402 (17) | 0.0341 (16) | −0.0036 (14) | 0.0058 (13) | 0.0070 (12) |
C6B | 0.0312 (15) | 0.0454 (17) | 0.0345 (16) | −0.0053 (13) | 0.0039 (12) | 0.0019 (12) |
C1C | 0.0364 (15) | 0.0384 (16) | 0.0302 (15) | −0.0058 (13) | 0.0031 (12) | −0.0007 (12) |
C11C | 0.0398 (17) | 0.0402 (17) | 0.0489 (18) | −0.0092 (14) | 0.0087 (14) | −0.0043 (14) |
O10C | 0.0444 (13) | 0.0514 (14) | 0.112 (2) | −0.0161 (11) | 0.0264 (13) | −0.0032 (13) |
O11C | 0.0675 (15) | 0.0399 (13) | 0.111 (2) | −0.0183 (12) | 0.0438 (14) | −0.0192 (12) |
C2C | 0.0328 (15) | 0.0415 (17) | 0.0334 (15) | −0.0028 (13) | 0.0041 (12) | 0.0008 (12) |
C3C | 0.0405 (16) | 0.0352 (16) | 0.0373 (16) | 0.0033 (13) | −0.0005 (13) | 0.0008 (12) |
C4C | 0.0425 (17) | 0.0355 (16) | 0.0305 (15) | −0.0115 (13) | −0.0036 (12) | 0.0019 (12) |
N41C | 0.0614 (18) | 0.0394 (16) | 0.0472 (16) | −0.0143 (14) | −0.0008 (13) | 0.0015 (12) |
O41C | 0.0916 (19) | 0.0352 (13) | 0.102 (2) | −0.0118 (13) | 0.0213 (15) | −0.0014 (12) |
O42C | 0.0616 (16) | 0.0569 (15) | 0.098 (2) | −0.0293 (13) | 0.0033 (14) | 0.0005 (13) |
C5C | 0.0334 (15) | 0.0423 (17) | 0.0392 (17) | −0.0094 (13) | 0.0031 (12) | −0.0008 (13) |
C6C | 0.0348 (16) | 0.0356 (16) | 0.0409 (16) | −0.0019 (12) | 0.0054 (12) | −0.0055 (12) |
N1D | 0.0457 (14) | 0.0402 (14) | 0.0417 (14) | −0.0102 (11) | −0.0039 (11) | 0.0080 (11) |
C2D | 0.059 (2) | 0.0352 (16) | 0.0456 (18) | −0.0131 (14) | −0.0024 (15) | 0.0032 (13) |
C3D | 0.0520 (19) | 0.0447 (18) | 0.0456 (18) | −0.0213 (15) | −0.0045 (14) | 0.0022 (14) |
N4D | 0.0472 (14) | 0.0393 (14) | 0.0418 (14) | −0.0058 (11) | −0.0055 (11) | 0.0033 (11) |
C1E | 0.0362 (15) | 0.0412 (16) | 0.0241 (14) | −0.0073 (13) | 0.0027 (11) | 0.0010 (11) |
C11E | 0.0370 (17) | 0.0380 (17) | 0.0377 (16) | −0.0073 (13) | 0.0014 (13) | 0.0017 (13) |
O10E | 0.0407 (12) | 0.0446 (12) | 0.0721 (15) | −0.0101 (10) | −0.0154 (11) | −0.0017 (10) |
O11E | 0.0458 (12) | 0.0442 (13) | 0.0778 (16) | −0.0130 (10) | −0.0106 (11) | 0.0206 (11) |
C2E | 0.0338 (15) | 0.0414 (17) | 0.0314 (15) | −0.0053 (13) | −0.0008 (12) | 0.0006 (12) |
C3E | 0.0474 (18) | 0.0372 (16) | 0.0326 (15) | −0.0011 (14) | 0.0035 (13) | 0.0041 (12) |
C4E | 0.0463 (17) | 0.0390 (16) | 0.0289 (15) | −0.0151 (14) | 0.0029 (12) | 0.0031 (12) |
N41E | 0.0640 (19) | 0.0482 (17) | 0.0463 (16) | −0.0216 (15) | 0.0051 (13) | −0.0001 (12) |
O41E | 0.091 (2) | 0.0445 (15) | 0.115 (2) | −0.0194 (14) | 0.0112 (17) | −0.0072 (14) |
O42E | 0.0630 (17) | 0.0728 (17) | 0.100 (2) | −0.0364 (14) | −0.0006 (14) | 0.0079 (14) |
C5E | 0.0347 (15) | 0.0523 (19) | 0.0314 (15) | −0.0169 (14) | −0.0001 (12) | 0.0039 (13) |
C6E | 0.0375 (16) | 0.0423 (17) | 0.0336 (15) | −0.0024 (13) | 0.0007 (12) | 0.0075 (12) |
C1F | 0.0357 (15) | 0.0390 (16) | 0.0291 (14) | −0.0085 (13) | −0.0036 (12) | 0.0052 (11) |
C11F | 0.0364 (17) | 0.0412 (18) | 0.0439 (18) | −0.0088 (14) | −0.0075 (13) | 0.0088 (13) |
O10F | 0.0420 (13) | 0.0591 (15) | 0.1002 (19) | −0.0191 (11) | 0.0105 (12) | 0.0015 (13) |
O11F | 0.0496 (13) | 0.0390 (12) | 0.0721 (15) | −0.0100 (10) | −0.0077 (11) | 0.0085 (10) |
C2F | 0.0311 (15) | 0.0456 (17) | 0.0347 (16) | −0.0026 (13) | 0.0016 (12) | 0.0028 (12) |
C3F | 0.0426 (17) | 0.0338 (16) | 0.0433 (17) | 0.0013 (13) | 0.0003 (13) | −0.0011 (12) |
C4F | 0.0426 (17) | 0.0340 (15) | 0.0341 (16) | −0.0087 (13) | −0.0036 (12) | 0.0057 (12) |
N41F | 0.0610 (19) | 0.0350 (15) | 0.0542 (17) | −0.0130 (14) | −0.0079 (14) | 0.0038 (12) |
O41F | 0.0772 (17) | 0.0350 (14) | 0.109 (2) | −0.0090 (13) | −0.0056 (15) | 0.0018 (13) |
O42F | 0.0583 (16) | 0.0611 (16) | 0.107 (2) | −0.0291 (13) | 0.0104 (14) | 0.0049 (14) |
C5F | 0.0323 (15) | 0.0401 (17) | 0.0342 (15) | −0.0050 (13) | 0.0015 (12) | 0.0041 (12) |
C6F | 0.0353 (15) | 0.0324 (15) | 0.0394 (16) | −0.0020 (12) | 0.0004 (12) | −0.0015 (12) |
O1W | 0.0437 (13) | 0.0387 (13) | 0.0655 (15) | −0.0073 (11) | 0.0181 (11) | −0.0025 (10) |
O2W | 0.0396 (13) | 0.0412 (13) | 0.0644 (15) | −0.0051 (11) | 0.0081 (11) | −0.0078 (10) |
O3W | 0.0388 (13) | 0.0424 (13) | 0.0617 (15) | −0.0109 (11) | −0.0039 (11) | 0.0073 (10) |
O4W | 0.0429 (13) | 0.0392 (12) | 0.0613 (14) | −0.0072 (11) | −0.0047 (11) | 0.0077 (10) |
Geometric parameters (Å, º) top
N1A—C2A | 1.514 (4) | C2D—C3D | 1.520 (4) |
N1A—H11A | 0.89 | C2D—H21D | 0.97 |
N1A—H12A | 0.89 | C2D—H22D | 0.97 |
N1A—H13A | 0.89 | C3D—N4D | 1.471 (3) |
C2A—C3A | 1.493 (4) | C3D—H31D | 0.97 |
C2A—H21A | 0.97 | C3D—H32D | 0.97 |
C2A—H22A | 0.97 | N4D—H41D | 0.89 |
C3A—N4A | 1.467 (3) | N4D—H42D | 0.89 |
C3A—H31A | 0.97 | N4D—H43D | 0.89 |
C3A—H32A | 0.97 | C1E—C2E | 1.391 (4) |
N4A—H41A | 0.89 | C1E—C6E | 1.406 (4) |
N4A—H42A | 0.89 | C1E—C11E | 1.517 (4) |
N4A—H43A | 0.89 | C11E—O10E | 1.252 (3) |
C1B—C6B | 1.388 (4) | C11E—O11E | 1.260 (3) |
C1B—C2B | 1.403 (4) | C2E—C3E | 1.380 (4) |
C1B—C11B | 1.507 (4) | C2E—H2E | 0.93 |
C11B—O11B | 1.229 (3) | C3E—C4E | 1.385 (4) |
C11B—O10B | 1.250 (3) | C3E—H3E | 0.93 |
C2B—C3B | 1.388 (4) | C4E—C5E | 1.376 (4) |
C2B—H2B | 0.93 | C4E—N41E | 1.467 (4) |
C3B—C4B | 1.381 (4) | N41E—O42E | 1.219 (3) |
C3B—H3B | 0.93 | N41E—O41E | 1.221 (3) |
C4B—C5B | 1.384 (4) | C5E—C6E | 1.384 (4) |
C4B—N41B | 1.471 (4) | C5E—H5E | 0.93 |
N41B—O42B | 1.219 (3) | C6E—H6E | 0.93 |
N41B—O41B | 1.234 (3) | C1F—C6F | 1.388 (4) |
C5B—C6B | 1.388 (4) | C1F—C2F | 1.389 (4) |
C5B—H5B | 0.93 | C1F—C11F | 1.502 (4) |
C6B—H6B | 0.93 | C11F—O10F | 1.234 (3) |
C1C—C6C | 1.387 (3) | C11F—O11F | 1.264 (3) |
C1C—C2C | 1.388 (4) | C2F—C3F | 1.376 (4) |
C1C—C11C | 1.505 (4) | C2F—H2F | 0.93 |
C11C—O10C | 1.226 (3) | C3F—C4F | 1.371 (4) |
C11C—O11C | 1.251 (3) | C3F—H3F | 0.93 |
C2C—C3C | 1.384 (4) | C4F—C5F | 1.380 (4) |
C2C—H2C | 0.93 | C4F—N41F | 1.480 (4) |
C3C—C4C | 1.367 (4) | N41F—O42F | 1.207 (3) |
C3C—H3C | 0.93 | N41F—O41F | 1.217 (3) |
C4C—C5C | 1.373 (4) | C5F—C6F | 1.383 (4) |
C4C—N41C | 1.474 (4) | C5F—H5F | 0.93 |
N41C—O42C | 1.215 (3) | C6F—H6F | 0.93 |
N41C—O41C | 1.222 (3) | O1W—H11 | 0.87 (4) |
C5C—C6C | 1.377 (4) | O1W—H12 | 0.91 (3) |
C5C—H5C | 0.93 | O2W—H21 | 0.94 (4) |
C6C—H6C | 0.93 | O2W—H22 | 0.85 (3) |
N1D—C2D | 1.509 (4) | O3W—H31 | 0.80 (3) |
N1D—H11D | 0.89 | O3W—H32 | 0.97 (3) |
N1D—H12D | 0.89 | O4W—H41 | 0.87 (4) |
N1D—H13D | 0.89 | O4W—H42 | 1.02 (4) |
| | | |
C2A—N1A—H11A | 109.5 | H11D—N1D—H12D | 109.5 |
C2A—N1A—H12A | 109.5 | C2D—N1D—H13D | 109.5 |
H11A—N1A—H12A | 109.5 | H11D—N1D—H13D | 109.5 |
C2A—N1A—H13A | 109.5 | H12D—N1D—H13D | 109.5 |
H11A—N1A—H13A | 109.5 | N1D—C2D—C3D | 114.3 (2) |
H12A—N1A—H13A | 109.5 | N1D—C2D—H21D | 108.7 |
C3A—C2A—N1A | 113.5 (2) | C3D—C2D—H21D | 108.7 |
C3A—C2A—H21A | 108.9 | N1D—C2D—H22D | 108.7 |
N1A—C2A—H21A | 108.9 | C3D—C2D—H22D | 108.7 |
C3A—C2A—H22A | 108.9 | H21D—C2D—H22D | 107.6 |
N1A—C2A—H22A | 108.9 | N4D—C3D—C2D | 113.3 (2) |
H21A—C2A—H22A | 107.7 | N4D—C3D—H31D | 108.9 |
N4A—C3A—C2A | 113.4 (2) | C2D—C3D—H31D | 108.9 |
N4A—C3A—H31A | 108.9 | N4D—C3D—H32D | 108.9 |
C2A—C3A—H31A | 108.9 | C2D—C3D—H32D | 108.9 |
N4A—C3A—H32A | 108.9 | H31D—C3D—H32D | 107.7 |
C2A—C3A—H32A | 108.9 | C3D—N4D—H41D | 109.5 |
H31A—C3A—H32A | 107.7 | C3D—N4D—H42D | 109.5 |
C3A—N4A—H41A | 109.5 | H41D—N4D—H42D | 109.5 |
C3A—N4A—H42A | 109.5 | C3D—N4D—H43D | 109.5 |
H41A—N4A—H42A | 109.5 | H41D—N4D—H43D | 109.5 |
C3A—N4A—H43A | 109.5 | H42D—N4D—H43D | 109.5 |
H41A—N4A—H43A | 109.5 | C2E—C1E—C6E | 119.4 (3) |
H42A—N4A—H43A | 109.5 | C2E—C1E—C11E | 118.8 (2) |
C6B—C1B—C2B | 119.4 (3) | C6E—C1E—C11E | 121.8 (3) |
C6B—C1B—C11B | 119.0 (2) | O10E—C11E—O11E | 124.6 (3) |
C2B—C1B—C11B | 121.6 (3) | O10E—C11E—C1E | 118.1 (3) |
O11B—C11B—O10B | 123.2 (3) | O11E—C11E—C1E | 117.3 (2) |
O11B—C11B—C1B | 117.6 (3) | C3E—C2E—C1E | 120.6 (3) |
O10B—C11B—C1B | 119.2 (2) | C3E—C2E—H2E | 119.7 |
C3B—C2B—C1B | 120.7 (3) | C1E—C2E—H2E | 119.7 |
C3B—C2B—H2B | 119.6 | C2E—C3E—C4E | 118.4 (3) |
C1B—C2B—H2B | 119.6 | C2E—C3E—H3E | 120.8 |
C4B—C3B—C2B | 118.1 (3) | C4E—C3E—H3E | 120.8 |
C4B—C3B—H3B | 121.0 | C5E—C4E—C3E | 123.0 (3) |
C2B—C3B—H3B | 121.0 | C5E—C4E—N41E | 118.0 (3) |
C3B—C4B—C5B | 122.7 (3) | C3E—C4E—N41E | 119.0 (3) |
C3B—C4B—N41B | 118.3 (3) | O42E—N41E—O41E | 122.5 (3) |
C5B—C4B—N41B | 119.0 (3) | O42E—N41E—C4E | 118.5 (3) |
O42B—N41B—O41B | 123.0 (3) | O41E—N41E—C4E | 119.0 (3) |
O42B—N41B—C4B | 118.1 (3) | C4E—C5E—C6E | 118.1 (3) |
O41B—N41B—C4B | 118.9 (3) | C4E—C5E—H5E | 121.0 |
C4B—C5B—C6B | 118.5 (3) | C6E—C5E—H5E | 121.0 |
C4B—C5B—H5B | 120.8 | C5E—C6E—C1E | 120.5 (3) |
C6B—C5B—H5B | 120.8 | C5E—C6E—H6E | 119.7 |
C1B—C6B—C5B | 120.6 (3) | C1E—C6E—H6E | 119.7 |
C1B—C6B—H6B | 119.7 | C6F—C1F—C2F | 118.7 (2) |
C5B—C6B—H6B | 119.7 | C6F—C1F—C11F | 121.0 (3) |
C6C—C1C—C2C | 118.7 (3) | C2F—C1F—C11F | 120.3 (2) |
C6C—C1C—C11C | 121.4 (2) | O10F—C11F—O11F | 125.1 (3) |
C2C—C1C—C11C | 119.9 (2) | O10F—C11F—C1F | 117.1 (3) |
O10C—C11C—O11C | 124.7 (3) | O11F—C11F—C1F | 117.8 (2) |
O10C—C11C—C1C | 116.9 (3) | C3F—C2F—C1F | 122.0 (3) |
O11C—C11C—C1C | 118.4 (2) | C3F—C2F—H2F | 119.0 |
C3C—C2C—C1C | 121.7 (2) | C1F—C2F—H2F | 119.0 |
C3C—C2C—H2C | 119.1 | C4F—C3F—C2F | 117.6 (3) |
C1C—C2C—H2C | 119.1 | C4F—C3F—H3F | 121.2 |
C4C—C3C—C2C | 117.3 (3) | C2F—C3F—H3F | 121.2 |
C4C—C3C—H3C | 121.3 | C3F—C4F—C5F | 122.6 (3) |
C2C—C3C—H3C | 121.3 | C3F—C4F—N41F | 118.1 (3) |
C3C—C4C—C5C | 123.0 (3) | C5F—C4F—N41F | 119.3 (2) |
C3C—C4C—N41C | 118.0 (3) | O42F—N41F—O41F | 123.5 (3) |
C5C—C4C—N41C | 119.0 (2) | O42F—N41F—C4F | 118.2 (3) |
O42C—N41C—O41C | 123.2 (3) | O41F—N41F—C4F | 118.3 (3) |
O42C—N41C—C4C | 118.2 (3) | C4F—C5F—C6F | 118.7 (2) |
O41C—N41C—C4C | 118.6 (3) | C4F—C5F—H5F | 120.6 |
C4C—C5C—C6C | 118.9 (2) | C6F—C5F—H5F | 120.6 |
C4C—C5C—H5C | 120.6 | C5F—C6F—C1F | 120.3 (3) |
C6C—C5C—H5C | 120.6 | C5F—C6F—H6F | 119.8 |
C5C—C6C—C1C | 120.4 (3) | C1F—C6F—H6F | 119.8 |
C5C—C6C—H6C | 119.8 | H11—O1W—H12 | 113 (3) |
C1C—C6C—H6C | 119.8 | H21—O2W—H22 | 105 (3) |
C2D—N1D—H11D | 109.5 | H31—O3W—H32 | 102 (3) |
C2D—N1D—H12D | 109.5 | H41—O4W—H42 | 107 (3) |
| | | |
N1A—C2A—C3A—N4A | −72.5 (4) | N1D—C2D—C3D—N4D | 73.6 (3) |
C6B—C1B—C11B—O11B | 30.2 (4) | C2E—C1E—C11E—O10E | 8.5 (4) |
C2B—C1B—C11B—O11B | −148.1 (3) | C6E—C1E—C11E—O10E | −171.5 (2) |
C6B—C1B—C11B—O10B | −148.7 (3) | C2E—C1E—C11E—O11E | −170.3 (2) |
C2B—C1B—C11B—O10B | 33.0 (4) | C6E—C1E—C11E—O11E | 9.7 (4) |
C6B—C1B—C2B—C3B | −0.8 (4) | C6E—C1E—C2E—C3E | −0.7 (4) |
C11B—C1B—C2B—C3B | 177.5 (2) | C11E—C1E—C2E—C3E | 179.3 (2) |
C1B—C2B—C3B—C4B | 1.9 (4) | C1E—C2E—C3E—C4E | 1.1 (4) |
C2B—C3B—C4B—C5B | −1.3 (4) | C2E—C3E—C4E—C5E | −0.6 (4) |
C2B—C3B—C4B—N41B | 178.4 (2) | C2E—C3E—C4E—N41E | 179.3 (2) |
C3B—C4B—N41B—O42B | −178.1 (3) | C5E—C4E—N41E—O42E | 20.2 (4) |
C5B—C4B—N41B—O42B | 1.6 (4) | C3E—C4E—N41E—O42E | −159.7 (3) |
C3B—C4B—N41B—O41B | 2.1 (4) | C5E—C4E—N41E—O41E | −159.4 (3) |
C5B—C4B—N41B—O41B | −178.2 (3) | C3E—C4E—N41E—O41E | 20.6 (4) |
C3B—C4B—C5B—C6B | −0.4 (4) | C3E—C4E—C5E—C6E | −0.2 (4) |
N41B—C4B—C5B—C6B | 179.9 (2) | N41E—C4E—C5E—C6E | 179.8 (2) |
C2B—C1B—C6B—C5B | −0.9 (4) | C4E—C5E—C6E—C1E | 0.7 (4) |
C11B—C1B—C6B—C5B | −179.3 (2) | C2E—C1E—C6E—C5E | −0.2 (4) |
C4B—C5B—C6B—C1B | 1.6 (4) | C11E—C1E—C6E—C5E | 179.8 (2) |
C6C—C1C—C11C—O10C | −176.7 (3) | C6F—C1F—C11F—O10F | −174.4 (3) |
C2C—C1C—C11C—O10C | 4.1 (4) | C2F—C1F—C11F—O10F | 5.3 (4) |
C6C—C1C—C11C—O11C | 2.5 (4) | C6F—C1F—C11F—O11F | 5.2 (4) |
C2C—C1C—C11C—O11C | −176.7 (3) | C2F—C1F—C11F—O11F | −175.1 (2) |
C6C—C1C—C2C—C3C | −0.3 (4) | C6F—C1F—C2F—C3F | −0.8 (4) |
C11C—C1C—C2C—C3C | 178.9 (3) | C11F—C1F—C2F—C3F | 179.5 (2) |
C1C—C2C—C3C—C4C | −0.2 (4) | C1F—C2F—C3F—C4F | 0.5 (4) |
C2C—C3C—C4C—C5C | 0.8 (4) | C2F—C3F—C4F—C5F | 0.0 (4) |
C2C—C3C—C4C—N41C | −179.4 (2) | C2F—C3F—C4F—N41F | −179.9 (2) |
C3C—C4C—N41C—O42C | −176.4 (3) | C3F—C4F—N41F—O42F | 176.8 (3) |
C5C—C4C—N41C—O42C | 3.4 (4) | C5F—C4F—N41F—O42F | −3.2 (4) |
C3C—C4C—N41C—O41C | 4.7 (4) | C3F—C4F—N41F—O41F | −2.8 (4) |
C5C—C4C—N41C—O41C | −175.5 (3) | C5F—C4F—N41F—O41F | 177.3 (3) |
C3C—C4C—C5C—C6C | −0.9 (4) | C3F—C4F—C5F—C6F | −0.3 (4) |
N41C—C4C—C5C—C6C | 179.4 (2) | N41F—C4F—C5F—C6F | 179.7 (2) |
C4C—C5C—C6C—C1C | 0.3 (4) | C4F—C5F—C6F—C1F | 0.0 (4) |
C2C—C1C—C6C—C5C | 0.3 (4) | C2F—C1F—C6F—C5F | 0.5 (4) |
C11C—C1C—C6C—C5C | −178.9 (3) | C11F—C1F—C6F—C5F | −179.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H11A···O2W | 0.89 | 2.03 | 2.833 (4) | 149 |
N1A—H12A···O1W | 0.89 | 1.99 | 2.786 (3) | 148 |
N1A—H13A···O11Bi | 0.89 | 1.85 | 2.744 (3) | 178 |
N4A—H41A···O1Wii | 0.89 | 2.09 | 2.881 (3) | 147 |
N4A—H42A···O2Wii | 0.89 | 2.09 | 2.861 (3) | 145 |
N4A—H43A···O10Bi | 0.89 | 1.96 | 2.847 (3) | 175 |
N1D—H11D···O4Wiii | 0.89 | 2.06 | 2.846 (3) | 147 |
N1D—H12D···O3W | 0.89 | 1.97 | 2.781 (3) | 150 |
N1D—H13D···O11E | 0.89 | 1.85 | 2.728 (3) | 171 |
N4D—H41D···O10E | 0.89 | 1.87 | 2.753 (3) | 173 |
N4D—H42D···O3Wii | 0.89 | 2.10 | 2.881 (4) | 146 |
N4D—H43D···O4Wiv | 0.89 | 2.04 | 2.839 (4) | 149 |
O1W—H11···O11Cv | 0.87 (4) | 1.86 (4) | 2.693 (3) | 160 (3) |
O1W—H12···O11C | 0.91 (3) | 1.77 (4) | 2.658 (3) | 166 (3) |
O2W—H21···O10C | 0.94 (4) | 1.72 (4) | 2.653 (3) | 171 (4) |
O2W—H22···O10B | 0.85 (3) | 1.87 (4) | 2.704 (3) | 168 (3) |
O3W—H31···O11Fvi | 0.80 (3) | 1.99 (3) | 2.785 (3) | 169 (3) |
O3W—H32···O11Fiii | 0.97 (3) | 1.70 (3) | 2.663 (3) | 174 (3) |
O4W—H41···O11E | 0.87 (4) | 1.88 (4) | 2.756 (3) | 176 (3) |
O4W—H42···O10F | 1.02 (4) | 1.65 (4) | 2.674 (3) | 177 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1; (iii) −x+1, −y, −z+1; (iv) −x+1, −y, −z; (v) −x, −y+1, −z+2; (vi) x−1, y, z. |
Experimental details
Crystal data |
Chemical formula | C2H10N22+·2C7H4NO4−·2H2O |
Mr | 430.38 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 12.213 (2), 22.317 (2), 7.091 (5) |
α, β, γ (°) | 89.47 (2), 89.17 (2), 84.72 (8) |
V (Å3) | 1924.2 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.40 × 0.20 × 0.10 |
|
Data collection |
Diffractometer | Rigaku AFC7-R diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6810, 6810, 3360 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.603 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.150, 1.00 |
No. of reflections | 6810 |
No. of parameters | 577 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.30 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H11A···O2W | 0.89 | 2.03 | 2.833 (4) | 149 |
N1A—H12A···O1W | 0.89 | 1.99 | 2.786 (3) | 148 |
N1A—H13A···O11Bi | 0.89 | 1.85 | 2.744 (3) | 178 |
N4A—H41A···O1Wii | 0.89 | 2.09 | 2.881 (3) | 147 |
N4A—H42A···O2Wii | 0.89 | 2.09 | 2.861 (3) | 145 |
N4A—H43A···O10Bi | 0.89 | 1.96 | 2.847 (3) | 175 |
N1D—H11D···O4Wiii | 0.89 | 2.06 | 2.846 (3) | 147 |
N1D—H12D···O3W | 0.89 | 1.97 | 2.781 (3) | 150 |
N1D—H13D···O11E | 0.89 | 1.85 | 2.728 (3) | 171 |
N4D—H41D···O10E | 0.89 | 1.87 | 2.753 (3) | 173 |
N4D—H42D···O3Wii | 0.89 | 2.10 | 2.881 (4) | 146 |
N4D—H43D···O4Wiv | 0.89 | 2.04 | 2.839 (4) | 149 |
O1W—H11···O11Cv | 0.87 (4) | 1.86 (4) | 2.693 (3) | 160 (3) |
O1W—H12···O11C | 0.91 (3) | 1.77 (4) | 2.658 (3) | 166 (3) |
O2W—H21···O10C | 0.94 (4) | 1.72 (4) | 2.653 (3) | 171 (4) |
O2W—H22···O10B | 0.85 (3) | 1.87 (4) | 2.704 (3) | 168 (3) |
O3W—H31···O11Fvi | 0.80 (3) | 1.99 (3) | 2.785 (3) | 169 (3) |
O3W—H32···O11Fiii | 0.97 (3) | 1.70 (3) | 2.663 (3) | 174 (3) |
O4W—H41···O11E | 0.87 (4) | 1.88 (4) | 2.756 (3) | 176 (3) |
O4W—H42···O10F | 1.02 (4) | 1.65 (4) | 2.674 (3) | 177 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1; (iii) −x+1, −y, −z+1; (iv) −x+1, −y, −z; (v) −x, −y+1, −z+2; (vi) x−1, y, z. |
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A search of the Cambridge Structural Database (Allen, 2002) reveals that there are 39 reported organic salt structures containing ethane-1,2-diamine and a carboxylate group. Of these, 11 contain a metal and can be considered as coordination complexes. The remainder can be separated into the 19 that contain an alkyl carboxylate whereas the rest (nine) contain benzoates. Interestingly, the majority (five) of these are nitrobenzoates, mainly 4-nitroanthranilate (Smith, Wermuth & White, 2002), 3,5-dinitrobenzoate (Nethaji et al., 1992; Lynch et al., 1994; Burchell et al., 2001) and 3,5-dinitrosalicylate (Smith, Wermuth, Bott et al., 2002). Here we report the 1:2 organic salt dihydrate of ethane-1,2-diammonium with 4-nitrobenzoate, (I) (Fig. 1).
The solid-state packing of (I) involves two symmetrically unique two-dimensional hydrogen-bonded networks individually derived from the repeat unit represented in Fig. 2 by molecules A–C, O1w and O2w. Both networks, comprising of molecules A–C, O1w and O2w, and D–F, O3w andO 4w, respectively, are essentially identical with the symmetry between the groupings being broken by the interdigitation of the 4-NBA molecules. Crosslinking through the associations of the water molecules to adjacent carboxylate O atoms creates the second dimension in the network. Hydrogen-bonding interactions are listed in Table 1.