Naphthalene-1,5-diammonium diiodide dihydrate

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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

Crystal data

C10H12N2^2+·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) Å^3	0.38 × 0.26 × 0.02 mm
Z = 2

Data collection

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

Refinement on F^2	3 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.016	w = 1/[σ^2(Fo^2) + (0.0184P)^2 + 0.2375P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

C1—C5^i	1.358 (4)	C4—C4^i	1.425 (4)
C1—C2	1.397 (4)	C5—C1^i	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)
C5^i—C1—C2	120.9 (3)	C5—C4—C4^i	119.2 (3)
C5^i—C1—H1	119.6	C1^i—C5—C4	120.7 (2)
C2—C1—H1	119.6	C1^i—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—C4^i	117.1 (3)	H1D—O1—H1E	106 (2)
C5^i—C1—C2—C3	0.1 (4)	C2—C3—C4—C4^i	−0.4 (4)
C1—C2—C3—C4	0.6 (4)	N1—C3—C4—C4^i	179.5 (3)
C1—C2—C3—N1	−179.3 (2)	C3—C4—C5—C1^i	179.3 (2)
C2—C3—C4—C5	179.1 (3)	C4^i—C4—C5—C1^i	−1.1 (4)
N1—C3—C4—C5	−0.9 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

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···O1^ii	0.89	2.14	2.954 (3)	151
O1—H1D···I1^iii	0.89 (2)	3.02 (3)	3.653 (2)	129 (2)
O1—H1E···I1^iv	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.