Propane-1,2-di­ammonium chromate(VI)

Trabelsi, S.; Essid, M.; Roisnel, T.; Rzaigui, M.; Marouani, H.

doi:10.1107/S1600536814002463

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages m84-m85

doi:10.1107/S1600536814002463

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Propane-1,2-diammonium chromate(VI)

Sonia Trabelsi,^a Manel Essid,^a ^* Thierry Roisnel,^b Mohamed Rzaigui ^a and Houda Marouani ^a

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and ^bCentre de Diffractométrie X, UMR 6226 CNRS, Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
^*Correspondence e-mail: essidmanel@voila.fr

(Received 3 February 2014; accepted 3 February 2014; online 8 February 2014)

In the title molecular salt, (C₃H₁₂N₂)[CrO₄], each chromate anion accepts six N—H⋯O and C—H⋯O hydrogen bonds from nearby propane-1,2-diammonium 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.

CCDC reference: 984845

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_r = 192.15
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.026
wR(F²) = 0.071
S = 1.14
1659 reflections
110 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.52 e Å⁻³

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⋯O1^iv	0.82 (3)	1.96 (3)	2.779 (2)	178 (2)
N2—H2B⋯O1^v	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⋯O2^iv	0.99	2.34	3.313 (2)	167
C3—H3B⋯O2ⁱⁱⁱ	0.98	2.37	3.301 (2)	158
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) x-1, y, z.

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).

Supporting information

CCDC reference: 984845

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

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

checkCIF report

Comment top

In this work, we report the preparation and the structural investigation of a new organic chromate, C₃H₁₂N₂·CrO₄ (I).

The asymmetric unit of (I) consists of one chromate anion and one propane-1,2-ammonium dication (Figure 1). The structure of the compound consists of discrete chromate ions stacked in layers parallel to the (100) plane, separated by organic cations (Figure 2). The structural cohesion is established by a three-dimensional network of N—H···O and C—H···O hydrogen bonds. Geometrical characteristics of the chromate anion are slightly different (Table 1). The distance Cr—O3 is notably the shortest (1.6182 (13) Å) because O3 is not applied in any hydrogen bond (Table 2) at the same time as Cr—O4 distance is the longest (1.6879 (13) Å) because O4 is applied in three hydrogen bonds. These geometrical features have also been noticed in other crystal structures (Chebbi & Driss, 2002; 2004; Srinivasan, et al., 2003).

The 1,2-propanediammonium cation is characterized by N—C—C—N and N—C—C—C torsion angles of 164.88 (14) and -74.50 (19)°, respectively. Each organic entity is bounded to six different chromate anions through eight N—H···O and C—H···O hydrogen bonds forming a three dimensional network. Examination of the 1,2-propanediammonium cation shows that the bond distances and angles show no significant difference from those obtained in other simple salts involving the same organic groups (Pospieszna-Markiewicz, et al., 2011; Gerrard, et al., 2002; Lee, et al., 2003; Todd, et al., 2005).

The established weak H-bonds (Brown, 1976; Blessing, 1986) of types N—H···O and C—H···O involve oxygen atoms of the chromate anions as acceptors, and the protonated nitrogen atoms and carbon atoms of 1,2-diammoniumpropane as donors.

Related literature top

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 top

CrO₃ (0.10 g, 1 mmol) and 1,2-diaminopropane (0.13 ml, 1 mmol) were dissolved in distilled water (20 ml). The resulting solution was stirred for 30 min. and then evaporated slowly at room temperature. Yellow prisms of the title compound were obtained from the solution after one week.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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).

Figures top

	Fig. 1. An ORTEP view of (I) with displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are shown as dotted lines.
	Fig. 2. Projection of (I) along the c axis. The H-atoms not involved in H-bonding are omitted.

Propane-1,2-diammonium chromate(VI) top

Crystal data top

(C₃H₁₂N₂)[CrO₄]	F(000) = 400
M_r = 192.15	D_x = 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

Data collection top

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

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)] = 0.026	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(F_o²) + (0.0303P)² + 0.5214P] where P = (F_o² + 2F_c²)/3
1659 reflections	(Δ/σ)_max = 0.001
110 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

(C₃H₁₂N₂)[CrO₄]	V = 722.94 (4) Å³
M_r = 192.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.6462 (2) Å	µ = 1.54 mm⁻¹
b = 15.8373 (5) Å	T = 150 K
c = 8.4442 (3) Å	0.55 × 0.44 × 0.31 mm
β = 106.779 (1)°

Data collection top

Bruker APEXII diffractometer	1659 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	1554 reflections with I > 2σ(I)
T_min = 0.477, T_max = 0.620	R_int = 0.032
6302 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.34 e Å⁻³
1659 reflections	Δρ_min = −0.52 e Å⁻³
110 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.82 (3)	1.96 (3)	2.779 (2)	178 (2)
N2—H2B···O1^v	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···O2^iv	0.99	2.34	3.313 (2)	167
C3—H3B···O2ⁱⁱⁱ	0.98	2.37	3.301 (2)	158

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

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.82 (3)	1.96 (3)	2.779 (2)	178 (2)
N2—H2B···O1^v	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···O2^iv	0.99	2.34	3.313 (2)	167
C3—H3B···O2ⁱⁱⁱ	0.98	2.37	3.301 (2)	158

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

Acknowledgements

This work was supported by the Tunisian Ministry of H. E. Sc. R.

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