[(5-Bromo-1H-indol-3-yl)meth­yl]dimethyl­aza­nium nitrate

Wang, Q.; Fu, Z.-Y.; Li, X.; Yu, L.-M.

doi:10.1107/S1600536811020034

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1671

doi:10.1107/S1600536811020034

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[(5-Bromo-1H-indol-3-yl)methyl]dimethylazanium nitrate

Qing Wang,^a ^* Zhong-Ye Fu,^a Xia Li ^a and Liang-Min Yu ^a

^aEducation Ministry Key Laboratory of Marine Chemistry and Technology, Ocean University of China, Qingdao, People's Republic of China
^*Correspondence e-mail: crystalshuai@yahoo.com.cn

(Received 17 May 2011; accepted 26 May 2011; online 18 June 2011)

In the title compound, C₁₁H₁₄BrN₂⁺·NO₃⁻, intermolecular N—H⋯O and N—H⋯N hydrogen bonds link the protonated 5-bromogramine cation and the nitrate anions. Further N—H⋯O hydrogen bonds link the cation–anion pairs into a chain running parallel to [100]. C—H⋯O hydrogen bonds link the chains, forming a layer parallel to (001).

Related literature

For background to gramine ramification, see: Kon-ya et al. (1994 ); Rie et al. (1996 ); Li et al. (2008 , 2009 ). For a related structure, see: Golubev & Kondrashev (1984 ).

Experimental

Crystal data

C₁₁H₁₄BrN₂⁺·NO₃⁻
M_r = 316.16
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.1449 (2) Å
b = 10.8270 (3) Å
c = 13.1344 (3) Å
V = 1300.46 (5) Å³
Z = 4
Cu Kα radiation
μ = 4.38 mm⁻¹
T = 150 K
0.50 × 0.42 × 0.40 mm

Data collection

Agilent Gemini S Ultra CCD diffractometer
2543 measured reflections
1760 independent reflections
1713 reflections with I > 2σ(I)
R_int = 0.022
θ_max = 62.4°

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.088
S = 1.07
1760 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.77 e Å⁻³
Absolute structure: Flack (1983 ), 546 Friedel pairs
Flack parameter: −0.01 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.91	2.24	3.041 (4)	146
N1—H1⋯O3	0.91	2.03	2.857 (4)	151
N1—H1⋯N3	0.91	2.49	3.391 (5)	169
N2—H2D⋯O2ⁱ	0.86	2.12	2.902 (4)	152
N2—H2D⋯O1ⁱ	0.86	2.65	3.388 (4)	144
C1—H1B⋯O3ⁱⁱ	0.96	2.45	3.293 (5)	146
C3—H3B⋯O3ⁱⁱ	0.97	2.40	3.259 (5)	147
Symmetry codes: (i) x-1, y, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010 ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1999 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020034/dn2690sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020034/dn2690Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536811020034/dn2690Isup3.cml

checkCIF report

Comment top

Recently, gramine ramification was shown to be very efficient in preventing recruitment of larval settlement. Many compounds such as 2,5,6-Tribromo-1-methylgramine (Kon-ya et al., 1994; Li et al., 2008; Li et al. 2009) and 5,6-dichlorogramine (Rie et al., 1996) have been reported. Here we report the synthesis and structure of the title compound (I).

The asymmetric unit contains one protonated 5-bromo-gramine and one NO₃¯ anion linked by a bifurcated N—H···O hydrogen bonds (Table 1, Fig. 1). Futhermore, intermolecular N—H···O hydrogen bonds link the cation-anion couple to form a one-dimensional chain running parallel to the [100] direction (Table 1). These chains are further connected through C—H···O hydrogen bonds to form layer parallel to the (0 0 1) plane (Table 1, Fig. 2).

Related literature top

For background to gramine ramification, see: Kon-ya et al. (1994); Rie et al. (1996); Li et al. (2008, 2009). For a related structure, see: Golubev et al. (1984).

Experimental top

Eu(NO₃)₃.6H₂O (0.2 mmol, 0.0892 g) was dissolved in CH₃OH (5 ml), and then carefully layered onto a solution of 5-BrG (0.2 mmol, 0.0504 g) in C₂H₅OH (5 ml). After the solvent was evaporated to almost dry, pale-yellow block crystals suitable for X-ray analysis could be harvested.

For (I): C₁₁H₁₄BrN₃O₃ (316.15, %): calcd. C 41.97, H 2.716, N 12.95; found C 41.79, H 4.46, N 13.29.

X-ray powder diffraction pattern was recorded to check the solid-state phase purity of the bulky sample of compound (I). Supplementary Figure 3 shows the measured pattern and the simulated one on the basis of single-crystal analysis result.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1999) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. : A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atom are represented as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
	Fig. 2. : Packing view of (I), showing the two-dimensional hydrogen-bonding layer. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity.
	Fig. 3. : The simulate X-ray powder diffraction pattern (upper) and the measured one (lower).

[(5-Bromo-1H-indol-3-yl)methyl]dimethylazanium nitrate top

Crystal data top

C₁₁H₁₄BrN₂⁺·NO₃⁻	F(000) = 640
M_r = 316.16	D_x = 1.615 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2128 reflections
a = 9.1449 (2) Å	θ = 3.4–62.3°
b = 10.8270 (3) Å	µ = 4.38 mm⁻¹
c = 13.1344 (3) Å	T = 150 K
V = 1300.46 (5) Å³	Block, yellow
Z = 4	0.50 × 0.42 × 0.40 mm

Data collection top

Agilent Gemini S Ultra CCD diffractometer	1713 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 62.4°, θ_min = 5.3°
Detector resolution: 16.0855 pixels mm^-1	h = −10→10
ϕ and ω scans	k = −12→11
2543 measured reflections	l = −14→13
1760 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.034	w = 1/[σ²(F_o²) + (0.0583P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.088	(Δ/σ)_max = 0.004
S = 1.07	Δρ_max = 0.60 e Å⁻³
1760 reflections	Δρ_min = −0.77 e Å⁻³
164 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0131 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 546 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.01 (3)

Crystal data top

C₁₁H₁₄BrN₂⁺·NO₃⁻	V = 1300.46 (5) Å³
M_r = 316.16	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 9.1449 (2) Å	µ = 4.38 mm⁻¹
b = 10.8270 (3) Å	T = 150 K
c = 13.1344 (3) Å	0.50 × 0.42 × 0.40 mm

Data collection top

Agilent Gemini S Ultra CCD diffractometer	1713 reflections with I > 2σ(I)
2543 measured reflections	R_int = 0.022
1760 independent reflections	θ_max = 62.4°

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.088	Δρ_max = 0.60 e Å⁻³
S = 1.07	Δρ_min = −0.77 e Å⁻³
1760 reflections	Absolute structure: Flack (1983), 546 Friedel pairs
164 parameters	Absolute structure parameter: −0.01 (3)
0 restraints

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
Br1	0.08934 (5)	0.37702 (4)	0.62866 (4)	0.0393 (2)
N1	0.0708 (3)	0.7763 (3)	0.2870 (2)	0.0218 (7)
H1	0.1132	0.7060	0.3108	0.026*
N2	−0.3723 (3)	0.6214 (3)	0.3766 (2)	0.0293 (8)
H2D	−0.4617	0.6044	0.3618	0.035*
C1	0.0076 (5)	0.7478 (4)	0.1850 (3)	0.0286 (9)
H1A	0.0844	0.7227	0.1396	0.043*
H1B	−0.0396	0.8201	0.1584	0.043*
H1C	−0.0625	0.6823	0.1914	0.043*
C2	0.1875 (4)	0.8720 (4)	0.2783 (3)	0.0308 (9)
H2A	0.2598	0.8452	0.2302	0.046*
H2B	0.2325	0.8840	0.3436	0.046*
H2C	0.1451	0.9483	0.2557	0.046*
C3	−0.0444 (4)	0.8157 (4)	0.3639 (3)	0.0254 (8)
H3A	0.0033	0.8342	0.4281	0.030*
H3B	−0.0909	0.8909	0.3401	0.030*
C4	−0.1584 (4)	0.7205 (4)	0.3813 (3)	0.0238 (8)
C5	−0.2987 (4)	0.7213 (4)	0.3437 (3)	0.0285 (9)
H5A	−0.3371	0.7822	0.3015	0.034*
C7	−0.2829 (4)	0.5507 (4)	0.4374 (3)	0.0218 (8)
C8	−0.3083 (5)	0.4384 (4)	0.4854 (3)	0.0284 (10)
H8A	−0.3982	0.3989	0.4796	0.034*
C9	−0.1965 (5)	0.3868 (4)	0.5421 (3)	0.0282 (9)
H9A	−0.2104	0.3119	0.5753	0.034*
C10	−0.0612 (4)	0.4490 (4)	0.5491 (3)	0.0245 (9)
C11	−0.0335 (4)	0.5599 (4)	0.5012 (3)	0.0225 (9)
H11A	0.0564	0.5992	0.5075	0.027*
C12	−0.1466 (4)	0.6110 (4)	0.4426 (3)	0.0200 (8)
N3	0.2674 (4)	0.5222 (3)	0.3505 (2)	0.0261 (8)
O1	0.3385 (4)	0.4266 (3)	0.3625 (3)	0.0462 (8)
O2	0.3106 (3)	0.6231 (3)	0.3859 (2)	0.0337 (7)
O3	0.1487 (3)	0.5214 (3)	0.3021 (2)	0.0309 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0454 (3)	0.0422 (3)	0.0301 (3)	0.0153 (2)	−0.0037 (2)	0.0094 (2)
N1	0.0305 (17)	0.0202 (15)	0.0147 (15)	0.0011 (16)	−0.0007 (14)	0.0015 (13)
N2	0.0227 (16)	0.045 (2)	0.0204 (16)	−0.0014 (16)	−0.0035 (14)	−0.001 (2)
C1	0.034 (2)	0.034 (2)	0.0178 (19)	0.001 (2)	−0.0023 (18)	−0.0059 (19)
C2	0.034 (2)	0.031 (2)	0.027 (2)	−0.008 (2)	0.0046 (17)	0.000 (2)
C3	0.035 (2)	0.0237 (18)	0.0174 (18)	0.0000 (17)	0.0033 (19)	−0.0012 (18)
C4	0.0308 (18)	0.0285 (19)	0.0122 (17)	0.0027 (17)	0.0021 (17)	−0.0017 (18)
C5	0.031 (2)	0.036 (2)	0.019 (2)	0.006 (2)	−0.0016 (16)	0.0021 (18)
C7	0.0233 (19)	0.030 (2)	0.0122 (17)	−0.0002 (18)	−0.0003 (16)	−0.0036 (17)
C8	0.033 (2)	0.033 (2)	0.0193 (19)	−0.009 (2)	0.0079 (17)	−0.0092 (19)
C9	0.039 (2)	0.026 (2)	0.0192 (19)	0.001 (2)	0.0065 (17)	−0.0019 (19)
C10	0.032 (2)	0.026 (2)	0.0149 (17)	0.0044 (18)	0.0018 (17)	0.0002 (17)
C11	0.0241 (19)	0.029 (2)	0.0146 (17)	−0.0013 (18)	0.0012 (16)	−0.0061 (17)
C12	0.0239 (17)	0.0251 (19)	0.0109 (16)	0.0044 (18)	0.0033 (14)	−0.0020 (17)
N3	0.0270 (17)	0.0253 (18)	0.0260 (18)	−0.0015 (16)	0.0049 (16)	0.0003 (16)
O1	0.0495 (18)	0.0319 (16)	0.057 (2)	0.0126 (15)	−0.0092 (19)	−0.0028 (18)
O2	0.0329 (15)	0.0293 (14)	0.0390 (17)	−0.0046 (13)	−0.0007 (13)	−0.0093 (17)
O3	0.0260 (14)	0.0357 (16)	0.0311 (15)	0.0003 (14)	−0.0033 (13)	−0.0038 (14)

Geometric parameters (Å, º) top

Br1—C10	1.896 (4)	C3—H3B	0.9700
N1—C1	1.491 (5)	C4—C5	1.375 (5)
N1—C2	1.492 (5)	C4—C12	1.437 (6)
N1—C3	1.521 (5)	C5—H5A	0.9300
N1—H1	0.9100	C7—C8	1.389 (6)
N2—C5	1.345 (6)	C7—C12	1.408 (5)
N2—C7	1.376 (5)	C8—C9	1.382 (6)
N2—H2D	0.8600	C8—H8A	0.9300
C1—H1A	0.9600	C9—C10	1.412 (6)
C1—H1B	0.9600	C9—H9A	0.9300
C1—H1C	0.9600	C10—C11	1.379 (6)
C2—H2A	0.9600	C11—C12	1.403 (5)
C2—H2B	0.9600	C11—H11A	0.9300
C2—H2C	0.9600	N3—O1	1.232 (4)
C3—C4	1.484 (5)	N3—O2	1.251 (4)
C3—H3A	0.9700	N3—O3	1.258 (4)

C1—N1—C2	110.6 (3)	C5—C4—C12	106.1 (3)
C1—N1—C3	112.8 (3)	C5—C4—C3	126.6 (4)
C2—N1—C3	110.5 (3)	C12—C4—C3	127.3 (3)
C1—N1—H1	107.6	N2—C5—C4	110.3 (4)
C2—N1—H1	107.6	N2—C5—H5A	124.9
C3—N1—H1	107.6	C4—C5—H5A	124.9
C5—N2—C7	109.7 (3)	N2—C7—C8	130.7 (4)
C5—N2—H2D	125.2	N2—C7—C12	107.2 (3)
C7—N2—H2D	125.2	C8—C7—C12	122.1 (4)
N1—C1—H1A	109.5	C9—C8—C7	118.3 (4)
N1—C1—H1B	109.5	C9—C8—H8A	120.8
H1A—C1—H1B	109.5	C7—C8—H8A	120.8
N1—C1—H1C	109.5	C8—C9—C10	119.4 (4)
H1A—C1—H1C	109.5	C8—C9—H9A	120.3
H1B—C1—H1C	109.5	C10—C9—H9A	120.3
N1—C2—H2A	109.5	C11—C10—C9	123.1 (4)
N1—C2—H2B	109.5	C11—C10—Br1	118.4 (3)
H2A—C2—H2B	109.5	C9—C10—Br1	118.5 (3)
N1—C2—H2C	109.5	C10—C11—C12	117.3 (4)
H2A—C2—H2C	109.5	C10—C11—H11A	121.4
H2B—C2—H2C	109.5	C12—C11—H11A	121.4
C4—C3—N1	113.2 (3)	C11—C12—C7	119.7 (4)
C4—C3—H3A	108.9	C11—C12—C4	133.5 (4)
N1—C3—H3A	108.9	C7—C12—C4	106.8 (3)
C4—C3—H3B	108.9	O1—N3—O2	121.3 (3)
N1—C3—H3B	108.9	O1—N3—O3	121.0 (3)
H3A—C3—H3B	107.8	O2—N3—O3	117.8 (3)

C1—N1—C3—C4	59.5 (4)	C8—C9—C10—Br1	179.3 (3)
C2—N1—C3—C4	−176.1 (3)	C9—C10—C11—C12	−0.5 (5)
N1—C3—C4—C5	−103.6 (4)	Br1—C10—C11—C12	179.8 (3)
N1—C3—C4—C12	78.1 (5)	C10—C11—C12—C7	2.0 (5)
C7—N2—C5—C4	0.0 (5)	C10—C11—C12—C4	−178.5 (4)
C12—C4—C5—N2	−0.3 (4)	N2—C7—C12—C11	179.2 (3)
C3—C4—C5—N2	−178.8 (4)	C8—C7—C12—C11	−2.7 (5)
C5—N2—C7—C8	−177.6 (4)	N2—C7—C12—C4	−0.5 (4)
C5—N2—C7—C12	0.3 (4)	C8—C7—C12—C4	177.7 (3)
N2—C7—C8—C9	179.4 (4)	C5—C4—C12—C11	−179.1 (4)
C12—C7—C8—C9	1.7 (6)	C3—C4—C12—C11	−0.6 (7)
C7—C8—C9—C10	−0.2 (6)	C5—C4—C12—C7	0.5 (4)
C8—C9—C10—C11	−0.4 (6)	C3—C4—C12—C7	179.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.91	2.24	3.041 (4)	146
N1—H1···O3	0.91	2.03	2.857 (4)	151
N1—H1···N3	0.91	2.49	3.391 (5)	169
N2—H2D···O2ⁱ	0.86	2.12	2.902 (4)	152
N2—H2D···O1ⁱ	0.86	2.65	3.388 (4)	144
C1—H1B···O3ⁱⁱ	0.96	2.45	3.293 (5)	146
C3—H3B···O3ⁱⁱ	0.97	2.40	3.259 (5)	147

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄BrN₂⁺·NO₃⁻
M_r	316.16
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	9.1449 (2), 10.8270 (3), 13.1344 (3)
V (Å³)	1300.46 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.38
Crystal size (mm)	0.50 × 0.42 × 0.40

Data collection
Diffractometer	Agilent Gemini S Ultra CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2543, 1760, 1713
R_int	0.022
θ_max (°)	62.4
(sin θ/λ)_max (Å⁻¹)	0.575

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.088, 1.07
No. of reflections	1760
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.77
Absolute structure	Flack (1983), 546 Friedel pairs
Absolute structure parameter	−0.01 (3)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.91	2.24	3.041 (4)	146
N1—H1···O3	0.91	2.03	2.857 (4)	151
N1—H1···N3	0.91	2.49	3.391 (5)	169
N2—H2D···O2ⁱ	0.86	2.12	2.902 (4)	152
N2—H2D···O1ⁱ	0.86	2.65	3.388 (4)	144
C1—H1B···O3ⁱⁱ	0.96	2.45	3.293 (5)	146
C3—H3B···O3ⁱⁱ	0.97	2.40	3.259 (5)	147

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

Acknowledgements

We acknowledge the support of the Postdoctoral Innovation Foundation of Shandong Province, the National Natural Science Foundation of China (No. 51003099) and the Special Foundation for Young Teachers of Ocean University of China (No. 201013017).

References

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