Propane-1,2-di-ammonium chromate(VI).

In the title mol-ecular salt, (C3H12N2)[CrO4], each chromate anion accepts six N-H⋯O and C-H⋯O hydrogen bonds from nearby propane-1,2-di-ammonium cations. Three of the four O atoms of the chromate anion accept these bonds; the remaining Cr-O bond length is notably shorter than the others. In the crystal, the anions and cations stack in layers lying parallel to (100): the hydrogen-bonding pattern leads to a three-dimensional network.

Related literature

For background to organic chromates, see: Chebbi & Driss (2002 ▶, 2004 ▶); Srinivasan et al. (2003 ▶). For the crystal structures of simple salts of the propane-1,2-di­ammonium cation, see: Pospieszna-Markiewicz et al. (2011 ▶); Gerrard & Weller (2002 ▶); Lee & Harrison (2003 ▶); Todd & Harrison (2005 ▶). For a discussion on hydrogen bonding, see: Brown (1976 ▶); Blessing (1986 ▶).

Experimental

Crystal data

(C3H12N2)[CrO4]

M = 192.15

Monoclinic,

a = 5.6462 (2) Å

b = 15.8373 (5) Å

c = 8.4442 (3) Å

β = 106.779 (1)°

V = 722.94 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.54 mm−1

T = 150 K

0.55 × 0.44 × 0.31 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.477, T max = 0.620

6302 measured reflections

1659 independent reflections

1554 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.071

S = 1.14

1659 reflections

110 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CRYSCAL (T. Roisnel, local program).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814002463/hb7193sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002463/hb7193Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

(C3H12N2)[CrO4]	F(000) = 400
Mr = 192.15	Dx = 1.765 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3695 reflections
a = 5.6462 (2) Å	θ = 2.8–27.5°
b = 15.8373 (5) Å	µ = 1.54 mm−1
c = 8.4442 (3) Å	T = 150 K
β = 106.779 (1)°	Prism, yellow
V = 722.94 (4) Å3	0.55 × 0.44 × 0.31 mm
Z = 4

Bruker APEXII diffractometer	1659 independent reflections
Radiation source: fine-focus sealed tube	1554 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −7→6
Tmin = 0.477, Tmax = 0.620	k = −19→20
6302 measured reflections	l = −9→10

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0303P)2 + 0.5214P] where P = (Fo2 + 2Fc2)/3
1659 reflections	(Δ/σ)max = 0.001
110 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cr	0.97996 (5)	0.114804 (17)	0.67966 (3)	0.00751 (11)
O1	1.0758 (2)	0.20744 (8)	0.77039 (15)	0.0120 (3)
O2	1.0791 (3)	0.03771 (9)	0.81142 (16)	0.0154 (3)
O3	1.0937 (3)	0.10356 (8)	0.52561 (16)	0.0146 (3)
O4	0.6684 (2)	0.11150 (8)	0.60744 (16)	0.0124 (3)
N1	0.5418 (3)	0.46519 (10)	0.7997 (2)	0.0112 (3)
H1A	0.606 (4)	0.4428 (16)	0.894 (3)	0.017*
H1B	0.456 (4)	0.5094 (16)	0.810 (3)	0.017*
H1C	0.660 (5)	0.4816 (15)	0.763 (3)	0.017*
N2	0.3804 (3)	0.25695 (10)	0.5858 (2)	0.0102 (3)
H2A	0.289 (5)	0.2680 (15)	0.494 (3)	0.015*
H2B	0.291 (4)	0.2454 (15)	0.648 (3)	0.015*
H2C	0.467 (4)	0.2134 (16)	0.581 (3)	0.015*
C1	0.3836 (3)	0.40086 (11)	0.6906 (2)	0.0107 (3)
H1	0.2885	0.4275	0.5855	0.013*
H2	0.2647	0.3774	0.7451	0.013*
C2	0.5446 (3)	0.32984 (11)	0.6549 (2)	0.0097 (3)
H3	0.6664	0.3121	0.7612	0.012*
C3	0.6845 (4)	0.35472 (12)	0.5330 (2)	0.0141 (4)
H3A	0.7805	0.3063	0.5133	0.021*
H3B	0.7967	0.4016	0.5786	0.021*
H3C	0.5667	0.3722	0.4284	0.021*

	U11	U22	U33	U12	U13	U23
Cr	0.00627 (16)	0.00701 (16)	0.00877 (16)	−0.00041 (10)	0.00140 (11)	−0.00009 (9)
O1	0.0121 (6)	0.0105 (6)	0.0129 (6)	−0.0018 (5)	0.0027 (5)	−0.0024 (5)
O2	0.0167 (7)	0.0130 (6)	0.0152 (6)	0.0031 (5)	0.0028 (5)	0.0037 (5)
O3	0.0151 (7)	0.0158 (6)	0.0145 (6)	−0.0032 (5)	0.0069 (5)	−0.0032 (5)
O4	0.0085 (6)	0.0122 (6)	0.0155 (6)	−0.0004 (5)	0.0021 (5)	−0.0011 (5)
N1	0.0127 (8)	0.0099 (7)	0.0110 (7)	0.0005 (6)	0.0035 (6)	−0.0014 (6)
N2	0.0105 (7)	0.0084 (7)	0.0116 (7)	−0.0006 (6)	0.0029 (6)	−0.0004 (6)
C1	0.0086 (8)	0.0102 (8)	0.0123 (8)	0.0002 (7)	0.0016 (7)	−0.0014 (6)
C2	0.0085 (8)	0.0085 (8)	0.0112 (8)	−0.0006 (6)	0.0014 (6)	−0.0011 (6)
C3	0.0135 (9)	0.0125 (8)	0.0185 (9)	−0.0021 (7)	0.0080 (7)	−0.0019 (7)

Cr—O3	1.6182 (13)	N2—H2B	0.85 (2)
Cr—O2	1.6378 (13)	N2—H2C	0.85 (3)
Cr—O1	1.6711 (13)	C1—C2	1.530 (2)
Cr—O4	1.6879 (13)	C1—H1	0.9900
N1—C1	1.486 (2)	C1—H2	0.9900
N1—H1A	0.85 (3)	C2—C3	1.520 (2)
N1—H1B	0.87 (3)	C2—H3	1.0000
N1—H1C	0.85 (3)	C3—H3A	0.9800
N2—C2	1.490 (2)	C3—H3B	0.9800
N2—H2A	0.82 (3)	C3—H3C	0.9800
O3—Cr—O2	109.08 (7)	N1—C1—C2	109.95 (14)
O3—Cr—O1	108.31 (6)	N1—C1—H1	109.7
O2—Cr—O1	109.94 (7)	C2—C1—H1	109.7
O3—Cr—O4	108.67 (7)	N1—C1—H2	109.7
O2—Cr—O4	109.78 (7)	C2—C1—H2	109.7
O1—Cr—O4	111.01 (6)	H1—C1—H2	108.2
C1—N1—H1A	108.1 (16)	N2—C2—C3	108.76 (14)
C1—N1—H1B	111.1 (16)	N2—C2—C1	108.00 (14)
H1A—N1—H1B	110 (2)	C3—C2—C1	113.43 (15)
C1—N1—H1C	112.0 (16)	N2—C2—H3	108.9
H1A—N1—H1C	107 (2)	C3—C2—H3	108.9
H1B—N1—H1C	108 (2)	C1—C2—H3	108.9
C2—N2—H2A	111.0 (16)	C2—C3—H3A	109.5
C2—N2—H2B	110.0 (16)	C2—C3—H3B	109.5
H2A—N2—H2B	108 (2)	H3A—C3—H3B	109.5
C2—N2—H2C	110.2 (16)	C2—C3—H3C	109.5
H2A—N2—H2C	110 (2)	H3A—C3—H3C	109.5
H2B—N2—H2C	108 (2)	H3B—C3—H3C	109.5
N1—C1—C2—N2	164.88 (14)	N1—C1—C2—C3	−74.50 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.85 (3)	1.94 (3)	2.769 (2)	166 (2)
N1—H1B···O4ii	0.87 (3)	1.97 (3)	2.816 (2)	164 (2)
N1—H1C···O2iii	0.85 (3)	1.97 (3)	2.818 (2)	171 (2)
N2—H2A···O1iv	0.82 (3)	1.96 (3)	2.779 (2)	178 (2)
N2—H2B···O1v	0.85 (2)	1.91 (3)	2.748 (2)	173 (2)
N2—H2C···O4	0.85 (3)	1.95 (3)	2.795 (2)	171 (2)
C1—H1···O2iv	0.99	2.34	3.313 (2)	167
C3—H3B···O2iii	0.98	2.37	3.301 (2)	158

Table 1

Selected bond lengths (Å)

Cr—O3	1.6182 (13)
Cr—O2	1.6378 (13)
Cr—O1	1.6711 (13)
Cr—O4	1.6879 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.85 (3)	1.94 (3)	2.769 (2)	166 (2)
N1—H1B⋯O4ii	0.87 (3)	1.97 (3)	2.816 (2)	164 (2)
N1—H1C⋯O2iii	0.85 (3)	1.97 (3)	2.818 (2)	171 (2)
N2—H2A⋯O1iv	0.82 (3)	1.96 (3)	2.779 (2)	178 (2)
N2—H2B⋯O1v	0.85 (2)	1.91 (3)	2.748 (2)	173 (2)
N2—H2C⋯O4	0.85 (3)	1.95 (3)	2.795 (2)	171 (2)
C1—H1⋯O2iv	0.99	2.34	3.313 (2)	167
C3—H3B⋯O2iii	0.98	2.37	3.301 (2)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .