A new amine phosphate templated by 1,4-diamino­cyclo­hexa­ne

The title compound, cyclo­hexane-1,4-diammonium bis­(di­hydrogen­phosphate), C₆H₁₆N₂²⁺·2H₂PO₄^-, was synthesized using the hydro­thermal method. It crystallizes with one anion and half a dication in the asymmetric unit; the latter lies on a centre of inversion. It has an inorganic network built up from (H₂PO₄)^- tetra­hedra linked together via strong hydrogen bonds to form infinite (H₂PO₄)^- sheets lying parallel to the (100) plane. The diprotonated amine mol­ecules link the layers together, assembling a three-dimensional hydrogen-bond network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.104
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: STADI4 (Stoe & Cie, 1998); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Diamond (Brandenburg, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

cyclohexane-1,4-diammonium bis(dihydrogenphosphate)

Crystal data

C6H16N2^2+·2H2O4P^−	F(000) = 328
Mr = 310.18	Dx = 1.642 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 32 reflections
a = 6.298 (3) Å	θ = 14.7–15.5°
b = 8.606 (2) Å	µ = 0.38 mm^−1
c = 11.824 (7) Å	T = 293 K
β = 101.84 (2)°	Plate, colourless
V = 627.2 (5) Å^3	0.24 × 0.13 × 0.05 mm
Z = 2

Data collection

Siemens AED2 diffractometer	1480 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.003
Graphite monochromator	θmax = 30.0°, θmin = 3.0°
2θ/ω scans	h = −8→8
Absorption correction: analytical (SHELXS76; Sheldrick, 1976)	k = 0→12
Tmin = 0.992, Tmax = 0.996	l = 0→16
1775 measured reflections	3 standard reflections every 120 reflections
1771 independent reflections	intensity decay: 3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	All H-atom parameters refined
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0563P)^2 + 0.3355P] where P = (Fo^2 + 2Fc^2)/3
1668 reflections	(Δ/σ)max = 0.011
122 parameters	Δρmax = 0.63 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.90033 (7)	0.07100 (5)	0.65335 (3)	0.01906 (13)
O1	0.8693 (2)	−0.07507 (16)	0.72831 (13)	0.0305 (3)
H1	0.972 (6)	−0.145 (5)	0.748 (3)	0.069 (10)*
O2	1.1478 (2)	0.07760 (16)	0.64862 (12)	0.0276 (3)
H2	1.169 (6)	0.044 (4)	0.591 (3)	0.056 (9)*
O3	0.8465 (2)	0.21281 (15)	0.71708 (11)	0.0278 (3)
O4	0.7640 (2)	0.04994 (16)	0.53428 (11)	0.0290 (3)
N	0.5412 (3)	0.23941 (18)	0.35683 (14)	0.0258 (3)
H0A	0.605 (4)	0.182 (3)	0.414 (2)	0.038 (7)*
H0B	0.421 (4)	0.201 (3)	0.315 (2)	0.038 (7)*
H0C	0.635 (5)	0.247 (3)	0.305 (2)	0.044 (7)*
C1	0.4974 (3)	0.39518 (19)	0.40346 (14)	0.0210 (3)
H1A	0.433 (4)	0.461 (3)	0.3387 (19)	0.027 (6)*
C2	0.7093 (3)	0.4640 (2)	0.46962 (16)	0.0247 (3)
H2A	0.777 (4)	0.393 (3)	0.532 (2)	0.028 (6)*
H2B	0.801 (5)	0.477 (3)	0.422 (2)	0.049 (8)*
C3	0.3315 (3)	0.3782 (2)	0.47980 (17)	0.0257 (3)
H3A	0.381 (4)	0.313 (3)	0.536 (2)	0.034 (6)*
H3B	0.199 (3)	0.334 (2)	0.4364 (17)	0.018 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0216 (2)	0.0158 (2)	0.0208 (2)	−0.00041 (13)	0.00699 (15)	−0.00196 (13)
O1	0.0304 (7)	0.0224 (6)	0.0410 (7)	0.0019 (5)	0.0130 (5)	0.0102 (5)
O2	0.0218 (6)	0.0361 (7)	0.0262 (6)	−0.0038 (5)	0.0082 (5)	−0.0063 (5)
O3	0.0347 (7)	0.0191 (6)	0.0340 (7)	−0.0022 (5)	0.0174 (5)	−0.0063 (5)
O4	0.0261 (6)	0.0349 (7)	0.0251 (6)	0.0049 (5)	0.0029 (5)	−0.0063 (5)
N	0.0259 (7)	0.0242 (7)	0.0288 (7)	−0.0002 (6)	0.0092 (6)	−0.0053 (6)
C1	0.0225 (7)	0.0192 (7)	0.0221 (7)	0.0005 (6)	0.0065 (6)	−0.0007 (5)
C2	0.0202 (7)	0.0268 (8)	0.0289 (8)	−0.0015 (6)	0.0093 (6)	−0.0038 (6)
C3	0.0234 (8)	0.0240 (8)	0.0323 (8)	−0.0052 (6)	0.0117 (7)	−0.0037 (7)

Geometric parameters (Å, º)

P1—O4	1.5022 (15)	N—H0C	0.94 (3)
P1—O3	1.5089 (13)	C1—C3	1.521 (2)
P1—O2	1.5724 (15)	C1—C2	1.522 (2)
P1—O1	1.5733 (14)	C1—H1A	0.97 (2)
O1—H1	0.88 (4)	C2—H2A	0.98 (2)
O2—H2	0.78 (3)	C2—H2B	0.89 (3)
N—C1	1.497 (2)	C3—C2^i	1.527 (2)
N—H0A	0.87 (3)	C3—H3A	0.88 (2)
N—H0B	0.88 (3)	C3—H3B	0.96 (2)
O4—P1—O3	114.95 (8)	C3—C1—C2	111.66 (14)
O4—P1—O2	110.57 (8)	N—C1—H1A	107.9 (14)
O3—P1—O2	108.33 (7)	C3—C1—H1A	107.3 (14)
O4—P1—O1	108.56 (9)	C2—C1—H1A	111.2 (14)
O3—P1—O1	107.36 (8)	C1—C2—C3^i	110.29 (14)
O2—P1—O1	106.72 (8)	C1—C2—H2A	110.1 (14)
P1—O1—H1	121 (2)	C3^i—C2—H2A	110.0 (14)
P1—O2—H2	112 (3)	C1—C2—H2B	109.6 (18)
C1—N—H0A	108.1 (18)	C3^i—C2—H2B	108.5 (19)
C1—N—H0B	109.7 (17)	H2A—C2—H2B	108 (2)
H0A—N—H0B	116 (2)	C1—C3—C2^i	109.79 (14)
C1—N—H0C	111.5 (17)	C1—C3—H3A	109.1 (17)
H0A—N—H0C	107 (2)	C2^i—C3—H3A	109.7 (16)
H0B—N—H0C	104 (2)	C1—C3—H3B	110.3 (12)
N—C1—C3	109.49 (14)	C2^i—C3—H3B	111.1 (12)
N—C1—C2	109.22 (14)	H3A—C3—H3B	107 (2)
H0C—N—C1—C2	−61.7 (18)	H0C—N—C1—H1A	59 (2)
H0A—N—C1—C2	56.1 (18)	H0B—N—C1—H1A	−56 (2)
H0A—N—C1—C3	−66.5 (18)	N—C1—C2—C3^i	−178.89 (14)
H0A—N—C1—H1A	177 (2)	C3—C1—C2—C3^i	−57.65 (19)
H0B—N—C1—C2	−176.7 (17)	C2—C1—C3—C2^i	57.34 (19)
H0B—N—C1—C3	60.7 (17)	N—C1—C3—C2^i	178.44 (15)
H0C—N—C1—C3	175.7 (18)	C1—C2—C3^i—C1^i	56.55 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O4	0.87 (3)	1.93 (3)	2.797 (2)	175 (3)
O2—H2···O4^ii	0.78 (3)	1.81 (3)	2.585 (2)	174 (3)
O1—H1···O3^iii	0.88 (4)	1.67 (4)	2.545 (2)	176 (4)
N—H0C···O3^iv	0.94 (3)	1.88 (3)	2.811 (2)	171 (2)
N—H0B···O1^v	0.88 (3)	2.10 (3)	2.937 (2)	160 (2)

Symmetry codes: (ii) −x+2, −y, −z+1; (iii) −x+2, y−1/2, −z+3/2; (iv) x, −y+1/2, z−1/2; (v) −x+1, −y, −z+1.