Bis(benzyl-trimethyl-ammonium) dichromate(VI).

The asymmetric part of the title compound, (C(10)H(16)N)(2)[Cr(2)O(7)], contains one cation and a half of the dichromate dianion, which has a staggered conformation and exhibits disorder of the bridging O atom around the inversion center over two positions in a 1:1 ratio. Weak inter-molecular C-H⋯O hydrogen bonds link cations and anions into a three-dimensional structure.

Related literature

For related structure, see: Jin et al. (2011 ▶).

Experimental

Crystal data

(C10H16N)2[Cr2O7]

M = 516.48

Monoclinic,

a = 8.8550 (18) Å

b = 12.442 (3) Å

c = 10.919 (2) Å

β = 91.75 (3)°

V = 1202.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.94 mm−1

T = 291 K

0.28 × 0.24 × 0.20 mm

Data collection

Rigaku Mercury2 (2x2 bin mode) diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.778, T max = 0.834

10940 measured reflections

2356 independent reflections

2070 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.108

S = 1.07

2356 reflections

148 parameters

60 restraints

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043091/cv5168sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043091/cv5168Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043091/cv5168Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C10H16N)2[Cr2O7]	Z = 2
Mr = 516.48	F(000) = 540
Monoclinic, P21/n	Dx = 1.427 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.8550 (18) Å	θ = 3.0–26.0°
b = 12.442 (3) Å	µ = 0.94 mm−1
c = 10.919 (2) Å	T = 291 K
β = 91.75 (3)°	Block, orange
V = 1202.4 (4) Å3	0.28 × 0.24 × 0.20 mm

Rigaku Mercury2 (2x2 bin mode) diffractometer	2356 independent reflections
Radiation source: fine-focus sealed tube	2070 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.0°
CCD_Profile_fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.778, Tmax = 0.834	l = −13→13
10940 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.057P)2 + 0.6088P] where P = (Fo2 + 2Fc2)/3
2356 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.42 e Å−3
60 restraints	Δρmin = −0.50 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	Occ. (<1)
C1	0.6409 (4)	0.8457 (3)	0.5418 (3)	0.0524 (7)
H1A	0.7118	0.8025	0.5884	0.079*
H1B	0.5473	0.8493	0.5838	0.079*
H1C	0.6809	0.9168	0.5326	0.079*
C2	0.5041 (4)	0.8658 (3)	0.3458 (3)	0.0558 (8)
H2A	0.5448	0.9370	0.3392	0.084*
H2B	0.4100	0.8687	0.3869	0.084*
H2C	0.4877	0.8361	0.2653	0.084*
C3	0.7592 (3)	0.7905 (2)	0.3526 (3)	0.0486 (7)
H3A	0.7981	0.8618	0.3418	0.073*
H3B	0.7423	0.7574	0.2739	0.073*
H3C	0.8308	0.7487	0.4001	0.073*
C4	0.5429 (3)	0.6849 (2)	0.4291 (3)	0.0470 (7)
H4A	0.4491	0.6919	0.4721	0.056*
H4B	0.5179	0.6583	0.3475	0.056*
C5	0.6397 (3)	0.6029 (2)	0.4944 (3)	0.0456 (7)
C6	0.6318 (4)	0.5878 (3)	0.6211 (3)	0.0541 (8)
H6	0.5700	0.6321	0.6664	0.065*
C7	0.7141 (4)	0.5085 (3)	0.6794 (3)	0.0649 (9)
H7	0.7074	0.4997	0.7636	0.078*
C8	0.8061 (4)	0.4422 (3)	0.6148 (4)	0.0681 (10)
H8	0.8624	0.3890	0.6549	0.082*
C9	0.8143 (4)	0.4550 (3)	0.4892 (4)	0.0670 (9)
H9	0.8755	0.4096	0.4447	0.080*
C10	0.7327 (4)	0.5344 (3)	0.4300 (3)	0.0537 (7)
H10	0.7397	0.5424	0.3457	0.064*
Cr1	0.10047 (4)	0.88613 (3)	0.53692 (4)	0.03659 (18)
N1	0.6137 (2)	0.79616 (18)	0.4177 (2)	0.0407 (5)
O1	0.2580 (3)	0.9159 (2)	0.6062 (2)	0.0755 (7)
O2	0.1341 (4)	0.8252 (3)	0.4124 (2)	0.0863 (8)
O3	0.0066 (8)	0.9953 (5)	0.4646 (4)	0.0720 (13)	0.50
O4	0.0014 (3)	0.8091 (2)	0.6192 (2)	0.0753 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0550 (17)	0.0549 (18)	0.0474 (16)	−0.0100 (15)	0.0024 (13)	−0.0200 (14)
C2	0.0458 (17)	0.0575 (19)	0.064 (2)	0.0067 (14)	−0.0047 (14)	−0.0065 (15)
C3	0.0398 (14)	0.0510 (16)	0.0555 (17)	−0.0065 (13)	0.0098 (12)	−0.0085 (13)
C4	0.0387 (14)	0.0534 (17)	0.0487 (15)	−0.0164 (12)	−0.0005 (12)	−0.0095 (13)
C5	0.0472 (15)	0.0467 (16)	0.0428 (14)	−0.0196 (12)	0.0002 (12)	−0.0070 (12)
C6	0.0624 (19)	0.0548 (18)	0.0452 (16)	−0.0195 (15)	0.0041 (14)	−0.0092 (14)
C7	0.085 (2)	0.062 (2)	0.0471 (17)	−0.0263 (19)	−0.0090 (17)	0.0004 (15)
C8	0.076 (2)	0.053 (2)	0.075 (2)	−0.0156 (18)	−0.0153 (19)	0.0049 (17)
C9	0.071 (2)	0.0492 (19)	0.082 (2)	−0.0072 (16)	0.0116 (18)	−0.0101 (17)
C10	0.0634 (19)	0.0508 (17)	0.0474 (16)	−0.0124 (15)	0.0093 (14)	−0.0062 (14)
Cr1	0.0359 (3)	0.0317 (3)	0.0421 (3)	0.00047 (16)	−0.00114 (18)	0.00768 (16)
N1	0.0331 (11)	0.0450 (12)	0.0439 (12)	−0.0033 (9)	0.0015 (9)	−0.0107 (10)
O1	0.0554 (14)	0.0929 (18)	0.0772 (16)	−0.0188 (13)	−0.0147 (12)	0.0001 (14)
O2	0.0880 (18)	0.104 (2)	0.0677 (16)	−0.0161 (16)	0.0182 (14)	−0.0238 (15)
O3	0.090 (3)	0.056 (2)	0.070 (3)	0.030 (2)	0.003 (3)	0.015 (3)
O4	0.0664 (14)	0.0954 (18)	0.0642 (14)	−0.0221 (13)	0.0029 (12)	0.0330 (13)

C1—N1	1.501 (3)	C5—C6	1.400 (4)
C1—H1A	0.9600	C6—C7	1.371 (5)
C1—H1B	0.9600	C6—H6	0.9300
C1—H1C	0.9600	C7—C8	1.370 (5)
C2—N1	1.504 (4)	C7—H7	0.9300
C2—H2A	0.9600	C8—C9	1.384 (5)
C2—H2B	0.9600	C8—H8	0.9300
C2—H2C	0.9600	C9—C10	1.373 (5)
C3—N1	1.492 (3)	C9—H9	0.9300
C3—H3A	0.9600	C10—H10	0.9300
C3—H3B	0.9600	Cr1—O2	1.593 (3)
C3—H3C	0.9600	Cr1—O4	1.595 (2)
C4—C5	1.498 (4)	Cr1—O1	1.610 (2)
C4—N1	1.527 (4)	Cr1—O3i	1.754 (6)
C4—H4A	0.9700	Cr1—O3	1.766 (6)
C4—H4B	0.9700	O3—O3i	0.794 (9)
C5—C10	1.392 (4)	O3—Cr1i	1.754 (6)
N1—C1—H1A	109.5	C8—C7—H7	119.7
N1—C1—H1B	109.5	C6—C7—H7	119.7
H1A—C1—H1B	109.5	C7—C8—C9	119.4 (4)
N1—C1—H1C	109.5	C7—C8—H8	120.3
H1A—C1—H1C	109.5	C9—C8—H8	120.3
H1B—C1—H1C	109.5	C10—C9—C8	120.4 (3)
N1—C2—H2A	109.5	C10—C9—H9	119.8
N1—C2—H2B	109.5	C8—C9—H9	119.8
H2A—C2—H2B	109.5	C9—C10—C5	120.9 (3)
N1—C2—H2C	109.5	C9—C10—H10	119.5
H2A—C2—H2C	109.5	C5—C10—H10	119.5
H2B—C2—H2C	109.5	O2—Cr1—O4	108.37 (16)
N1—C3—H3A	109.5	O2—Cr1—O1	109.21 (16)
N1—C3—H3B	109.5	O4—Cr1—O1	110.92 (14)
H3A—C3—H3B	109.5	O2—Cr1—O3i	120.51 (19)
N1—C3—H3C	109.5	O4—Cr1—O3i	101.8 (2)
H3A—C3—H3C	109.5	O1—Cr1—O3i	105.7 (3)
H3B—C3—H3C	109.5	O2—Cr1—O3	94.7 (2)
C5—C4—N1	115.2 (2)	O4—Cr1—O3	117.0 (3)
C5—C4—H4A	108.5	O1—Cr1—O3	115.0 (3)
N1—C4—H4A	108.5	O3i—Cr1—O3	26.1 (3)
C5—C4—H4B	108.5	C3—N1—C1	109.4 (2)
N1—C4—H4B	108.5	C3—N1—C2	109.3 (2)
H4A—C4—H4B	107.5	C1—N1—C2	108.6 (2)
C10—C5—C6	117.7 (3)	C3—N1—C4	111.0 (2)
C10—C5—C4	121.0 (3)	C1—N1—C4	110.7 (2)
C6—C5—C4	121.1 (3)	C2—N1—C4	107.8 (2)
C7—C6—C5	120.9 (3)	O3i—O3—Cr1i	77.8 (9)
C7—C6—H6	119.5	O3i—O3—Cr1	76.1 (8)
C5—C6—H6	119.5	Cr1i—O3—Cr1	153.9 (3)
C8—C7—C6	120.7 (3)
N1—C4—C5—C10	−93.3 (3)	C5—C4—N1—C3	58.0 (3)
N1—C4—C5—C6	91.1 (3)	C5—C4—N1—C1	−63.7 (3)
C10—C5—C6—C7	0.4 (4)	C5—C4—N1—C2	177.7 (2)
C4—C5—C6—C7	176.2 (3)	O2—Cr1—O3—O3i	172.0 (11)
C5—C6—C7—C8	0.0 (5)	O4—Cr1—O3—O3i	58.6 (12)
C6—C7—C8—C9	−0.7 (5)	O1—Cr1—O3—O3i	−74.2 (11)
C7—C8—C9—C10	0.9 (5)	O2—Cr1—O3—Cr1i	172.0 (11)
C8—C9—C10—C5	−0.4 (5)	O4—Cr1—O3—Cr1i	58.6 (12)
C6—C5—C10—C9	−0.3 (4)	O1—Cr1—O3—Cr1i	−74.2 (11)
C4—C5—C10—C9	−176.0 (3)	O3i—Cr1—O3—Cr1i	0.0

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O4ii	0.96	2.58	3.308 (4)	133.
C2—H2A···O1iii	0.96	2.59	3.467 (4)	153.
C2—H2B···O2	0.96	2.53	3.416 (5)	154.
C2—H2C···O4iv	0.96	2.42	3.294 (4)	152.
C4—H4B···O4iv	0.97	2.52	3.393 (4)	149.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O4i	0.96	2.58	3.308 (4)	133
C2—H2A⋯O1ii	0.96	2.59	3.467 (4)	153
C2—H2B⋯O2	0.96	2.53	3.416 (5)	154
C2—H2C⋯O4iii	0.96	2.42	3.294 (4)	152
C4—H4B⋯O4iii	0.97	2.52	3.393 (4)	149

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