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Naphthalene-1,5-diammonium diiodide crystallizes as the dihydrate, C10H12N22+·2I−·2H2O, and the crystal structure exhibits ionic layers separated by hydrocarbon layers. The naphthalene-1,5-diammonium cations in the hydrocarbon layers do not pack parallel to each other but alternate. In the ionic layer, the ammonium groups, the water molecules and the I− anions interact via hydrogen-bond bridges to form two infinite hydrogen-bonded chains.
Supporting information
CCDC reference: 604983
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.016
- wR factor = 0.041
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.14 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: XPREP; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg,
1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
Naphthalene-1,5-diammonium diiodide dihydrate
top
Crystal data top
C10H12N22+·2I−·2H2O | F(000) = 424 |
Mr = 450.05 | Dx = 2.14 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1014 reflections |
a = 11.353 (4) Å | θ = 3.7–28.2° |
b = 7.827 (3) Å | µ = 4.49 mm−1 |
c = 8.217 (3) Å | T = 293 K |
β = 106.921 (5)° | Plate, white |
V = 698.6 (4) Å3 | 0.38 × 0.26 × 0.02 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1190 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.036 |
Absorption correction: integration (XPREP; Bruker, 1999) | θmax = 25.5°, θmin = 1.9° |
Tmin = 0.294, Tmax = 0.912 | h = −13→13 |
7024 measured reflections | k = −9→9 |
1306 independent reflections | l = −9→9 |
Refinement top
Refinement on F2 | 3 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.016 | w = 1/[σ2(Fo2) + (0.0184P)2 + 0.2375P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.041 | (Δ/σ)max = 0.002 |
S = 1.14 | Δρmax = 0.29 e Å−3 |
1306 reflections | Δρmin = −0.41 e Å−3 |
80 parameters | |
Special details top
Experimental. Numerical integration absorption corrections based on indexed crystal faces were
applied using the XPREP routine (Bruker, 1999) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4672 (3) | 0.3995 (3) | 0.2739 (4) | 0.0360 (6) | |
H1 | 0.4353 | 0.3651 | 0.3609 | 0.043* | |
C2 | 0.5946 (2) | 0.4089 (3) | 0.3042 (3) | 0.0340 (6) | |
H2 | 0.6473 | 0.3808 | 0.4105 | 0.041* | |
C3 | 0.6408 (2) | 0.4594 (3) | 0.1774 (3) | 0.0284 (5) | |
C4 | 0.5649 (2) | 0.5050 (3) | 0.0141 (3) | 0.0262 (5) | |
C5 | 0.6108 (2) | 0.5601 (3) | −0.1193 (3) | 0.0307 (5) | |
H5 | 0.6953 | 0.5688 | −0.1011 | 0.037* | |
N1 | 0.77470 (18) | 0.4669 (3) | 0.2103 (3) | 0.0330 (5) | |
H1A | 0.7956 | 0.4128 | 0.1275 | 0.05* | |
H1B | 0.8113 | 0.4169 | 0.3094 | 0.05* | |
H1C | 0.7985 | 0.5755 | 0.2138 | 0.05* | |
I1 | 0.876547 (15) | 0.88292 (2) | 0.15879 (2) | 0.03570 (8) | |
O1 | 0.86464 (17) | 0.3078 (3) | −0.0376 (3) | 0.0389 (4) | |
H1D | 0.935 (2) | 0.260 (4) | 0.020 (3) | 0.047* | |
H1E | 0.884 (3) | 0.381 (3) | −0.109 (4) | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0365 (14) | 0.0399 (15) | 0.0341 (14) | −0.0022 (11) | 0.0142 (12) | 0.0045 (11) |
C2 | 0.0343 (14) | 0.0376 (14) | 0.0279 (13) | 0.0002 (11) | 0.0058 (11) | 0.0035 (10) |
C3 | 0.0235 (12) | 0.0304 (13) | 0.0300 (13) | −0.0005 (10) | 0.0058 (10) | −0.0012 (10) |
C4 | 0.0257 (12) | 0.0238 (11) | 0.0288 (12) | −0.0019 (9) | 0.0074 (10) | −0.0021 (9) |
C5 | 0.0256 (13) | 0.0339 (13) | 0.0332 (13) | −0.0027 (10) | 0.0093 (10) | 0.0015 (10) |
N1 | 0.0254 (10) | 0.0397 (12) | 0.0313 (11) | −0.0017 (9) | 0.0042 (9) | 0.0020 (9) |
I1 | 0.03438 (11) | 0.03823 (12) | 0.03446 (11) | 0.00064 (7) | 0.00994 (8) | 0.00205 (7) |
O1 | 0.0334 (10) | 0.0424 (11) | 0.0395 (11) | 0.0029 (9) | 0.0085 (9) | 0.0024 (8) |
Geometric parameters (Å, º) top
C1—C5i | 1.358 (4) | C4—C4i | 1.425 (4) |
C1—C2 | 1.397 (4) | C5—C1i | 1.358 (4) |
C1—H1 | 0.93 | C5—H5 | 0.93 |
C2—C3 | 1.354 (3) | N1—H1A | 0.89 |
C2—H2 | 0.93 | N1—H1B | 0.89 |
C3—C4 | 1.414 (3) | N1—H1C | 0.89 |
C3—N1 | 1.466 (3) | O1—H1D | 0.89 (2) |
C4—C5 | 1.411 (3) | O1—H1E | 0.89 (2) |
| | | |
C5i—C1—C2 | 120.9 (3) | C5—C4—C4i | 119.2 (3) |
C5i—C1—H1 | 119.6 | C1i—C5—C4 | 120.7 (2) |
C2—C1—H1 | 119.6 | C1i—C5—H5 | 119.6 |
C3—C2—C1 | 119.4 (2) | C4—C5—H5 | 119.6 |
C3—C2—H2 | 120.3 | C3—N1—H1A | 109.5 |
C1—C2—H2 | 120.3 | C3—N1—H1B | 109.5 |
C2—C3—C4 | 122.6 (2) | H1A—N1—H1B | 109.5 |
C2—C3—N1 | 118.9 (2) | C3—N1—H1C | 109.5 |
C4—C3—N1 | 118.5 (2) | H1A—N1—H1C | 109.5 |
C3—C4—C5 | 123.6 (2) | H1B—N1—H1C | 109.5 |
C3—C4—C4i | 117.1 (3) | H1D—O1—H1E | 106 (2) |
| | | |
C5i—C1—C2—C3 | 0.1 (4) | C2—C3—C4—C4i | −0.4 (4) |
C1—C2—C3—C4 | 0.6 (4) | N1—C3—C4—C4i | 179.5 (3) |
C1—C2—C3—N1 | −179.3 (2) | C3—C4—C5—C1i | 179.3 (2) |
C2—C3—C4—C5 | 179.1 (3) | C4i—C4—C5—C1i | −1.1 (4) |
N1—C3—C4—C5 | −0.9 (4) | | |
Symmetry code: (i) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···I1 | 0.89 | 2.65 | 3.522 (2) | 167 |
N1—H1A···O1 | 0.89 | 1.94 | 2.820 (3) | 172 |
N1—H1B···O1ii | 0.89 | 2.14 | 2.954 (3) | 151 |
O1—H1D···I1iii | 0.89 (2) | 3.02 (3) | 3.653 (2) | 129 (2) |
O1—H1E···I1iv | 0.89 (2) | 2.64 (2) | 3.507 (2) | 165 (3) |
Symmetry codes: (ii) x, −y+1/2, z+1/2; (iii) −x+2, y−1/2, −z+1/2; (iv) x, −y+3/2, z−1/2. |
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