2-[(N-Benzyl-4-methyl­benzene­sul­fon­amido)meth­yl]pyridinium nitrate

Li, J.-S.; Simpson, J.

doi:10.1107/S1600536809042330

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2814

https://doi.org/10.1107/S1600536809042330

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2-[(N-Benzyl-4-methylbenzenesulfonamido)methyl]pyridinium nitrate

Jiang-Sheng Li ^a ^* and Jim Simpson ^b

^aSchool of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410004, People's Republic of China, and ^bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: js_li@yahoo.com.cn

(Received 11 October 2009; accepted 15 October 2009; online 23 October 2009)

In the title compound, C₂₀H₂₁N₂O₂S⁺·NO₃⁻, the dihedral angle between the pyridinium and phenyl rings is 81.77 (19)°, that between the pyridinium and tolyl rings is 1.36 (18)°, and that between the phenyl and tolyl rings is 82.69 (19)°. In the crystal, the components are linked by strong charge-assisted bifurcated N⁺—H⋯(O,O) hydrogen bonds and the packing is consolidated by numerous weak C—H⋯O bonds and π–π stacking interactions [for the latter, centroid–centroid separation = 3.868 (2) Å].

Related literature

For the preparation of the title compound and for a related structure, see: Zhang et al. (2007 ).

Experimental

Crystal data

C₂₀H₂₁N₂O₂S⁺·NO₃⁻
M_r = 415.46
Triclinic, $[P \overline 1]$
a = 7.6852 (15) Å
b = 9.811 (2) Å
c = 13.240 (3) Å
α = 104.26 (3)°
β = 91.82 (3)°
γ = 95.64 (2)°
V = 961.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.960, T_max = 0.976
7087 measured reflections
3355 independent reflections
2020 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.188
S = 0.94
3355 reflections
267 parameters
18 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.91 (4)	1.82 (4)	2.670 (5)	156 (3)
N1—H1A⋯O4	0.91 (4)	2.39 (4)	3.161 (5)	144 (3)
C6—H6B⋯O3	0.99	2.66	3.362 (5)	128
C15—H15⋯O4	0.95	2.68	3.493 (5)	144
C1—H1⋯O2ⁱ	0.95	2.71	3.315 (5)	122
C3—H3⋯O1ⁱⁱ	0.95	2.60	3.301 (5)	131
C20—H20A⋯O3ⁱⁱⁱ	0.98	2.43	3.256 (5)	142
C7—H7A⋯O4^iv	0.99	2.70	3.440 (5)	132
C11—H11⋯O4^v	0.95	2.54	3.439 (5)	158
C11—H11⋯O5^v	0.95	2.55	3.411 (5)	151
C20—H20C⋯O3^vi	0.98	2.62	3.594 (5)	174
C10—H10⋯O5^vii	0.95	2.66	3.309 (6)	126
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+2, -z+2; (iii) x-1, y, z; (iv) x, y+1, z; (v) x+1, y+1, z; (vi) -x, -y+1, -z+1; (vii) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 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) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809042330/hb5137sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042330/hb5137Isup2.hkl

checkCIF report

Comment top

The molecular structure of (I) (Fig. 1) shows that the nitrate is connected with its corresponding pyridinium via two strong charge-assisted N⁺—H···O hydrogen bonds. In the cation, the dihedral angle between the pyridinium and phenyl rings is 81.774 (9)°, that between the pyridinium and tolyl rings 1.355 (5)°, and that between the phenyl and tolyl rings 82.693 (7)°.

In the crystal structure, a series of intermolecular C—H···O interactions link the molecules (Table 1), Fig. 2, which are packed by π-π stacking interactions between the pyridinium ring and the tolyl ring at (1 + x, y, z) [centroid-to -centroid separation 3.868 Å], together with two weak C—H···π interactions [H19···Cg2(x - 1, y, z) 2.90 Å, H20B···Cg3(-x, y, z) 2.69 Å; Cg2 and Cg3 are the centroids of the phenyl and tolyl rings,respectively], Fig.3.

Related literature top

For the preparation of the title compound and for a related structure, see: Zhang et al. (2007).

Experimental top

The tosylamino-containing pyridine derivative was prepared by a similar method to that of Zhang et al. (2007). Colourless needles of (I) were obtained by natural evaporation from its aqueous nitric acid solution.

Structure description top

For the preparation of the title compound and for a related structure, see: Zhang et al. (2007).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of (I) showing displacement ellipsoids drawn at the 30% probability level and H atoms shown as spheres of arbitrary radius.
	Fig. 2. Crystal packing of (I). Hydrogen bonds are indicated as dashed lines.
	Fig. 3. Crystal packing of (I) via π-π and C—H···π interactions, indicated as dashed lines.

2-[(N-Benzyl-4-methylbenzenesulfonamido)methyl]pyridinium nitrate top

Crystal data top

C₂₀H₂₁N₂O₂S⁺·NO₃⁻	Z = 2
M_r = 415.46	F(000) = 436
Triclinic, P1	D_x = 1.435 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6852 (15) Å	Cell parameters from 2706 reflections
b = 9.811 (2) Å	θ = 2.2–27.9°
c = 13.240 (3) Å	µ = 0.21 mm⁻¹
α = 104.26 (3)°	T = 113 K
β = 91.82 (3)°	Cut needle, colourless
γ = 95.64 (2)°	0.20 × 0.18 × 0.12 mm
V = 961.2 (3) Å³

Data collection top

Rigaku Saturn CCD diffractometer	3355 independent reflections
Radiation source: fine-focus sealed tube	2020 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 1.6°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −11→10
T_min = 0.960, T_max = 0.976	l = −13→15
7087 measured reflections

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ²(F_o²) + (0.0858P)²] where P = (F_o² + 2F_c²)/3
3355 reflections	(Δ/σ)_max = 0.002
267 parameters	Δρ_max = 0.76 e Å⁻³
18 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

C₂₀H₂₁N₂O₂S⁺·NO₃⁻	γ = 95.64 (2)°
M_r = 415.46	V = 961.2 (3) Å³
Triclinic, P1	Z = 2
a = 7.6852 (15) Å	Mo Kα radiation
b = 9.811 (2) Å	µ = 0.21 mm⁻¹
c = 13.240 (3) Å	T = 113 K
α = 104.26 (3)°	0.20 × 0.18 × 0.12 mm
β = 91.82 (3)°

Data collection top

Rigaku Saturn CCD diffractometer	3355 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2020 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.976	R_int = 0.099
7087 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	18 restraints
wR(F²) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.76 e Å⁻³
3355 reflections	Δρ_min = −0.73 e Å⁻³
267 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
S1	0.18143 (12)	0.79196 (10)	0.86138 (8)	0.0205 (3)
O1	0.1109 (3)	0.9220 (3)	0.9041 (2)	0.0274 (7)
O2	0.2282 (3)	0.7040 (3)	0.9273 (2)	0.0246 (7)
N1	0.5863 (4)	0.5427 (4)	0.8435 (3)	0.0227 (8)
N2	0.3629 (4)	0.8340 (3)	0.8070 (2)	0.0182 (8)
C1	0.6827 (5)	0.4979 (4)	0.9147 (3)	0.0263 (10)
H1	0.6861	0.3995	0.9078	0.032*
C2	0.7735 (5)	0.5931 (4)	0.9951 (3)	0.0256 (10)
H2	0.8407	0.5620	1.0449	0.031*
C3	0.7679 (5)	0.7362 (4)	1.0043 (3)	0.0240 (10)
H3	0.8321	0.8043	1.0599	0.029*
C4	0.6674 (5)	0.7786 (4)	0.9313 (3)	0.0234 (10)
H4	0.6620	0.8764	0.9368	0.028*
C5	0.5758 (5)	0.6794 (4)	0.8510 (3)	0.0178 (9)
C6	0.4652 (5)	0.7138 (4)	0.7666 (3)	0.0204 (9)
H6A	0.5421	0.7370	0.7132	0.024*
H6B	0.3836	0.6294	0.7322	0.024*
C7	0.3525 (5)	0.9325 (4)	0.7392 (3)	0.0225 (10)
H7A	0.2762	1.0060	0.7695	0.027*
H7B	0.3007	0.8802	0.6693	0.027*
C8	0.5338 (5)	1.0014 (4)	0.7292 (3)	0.0190 (9)
C9	0.6059 (5)	0.9836 (4)	0.6327 (3)	0.0246 (10)
H9	0.5395	0.9303	0.5715	0.030*
C10	0.7760 (5)	1.0438 (4)	0.6253 (4)	0.0285 (11)
H10	0.8249	1.0324	0.5591	0.034*
C11	0.8726 (5)	1.1195 (4)	0.7142 (4)	0.0277 (11)
H11	0.9891	1.1589	0.7094	0.033*
C12	0.8006 (5)	1.1386 (4)	0.8104 (4)	0.0254 (10)
H12	0.8675	1.1913	0.8716	0.030*
C13	0.6312 (5)	1.0808 (4)	0.8175 (3)	0.0232 (10)
H13	0.5813	1.0957	0.8836	0.028*
C14	0.0365 (5)	0.6861 (4)	0.7588 (3)	0.0182 (9)
C15	0.0291 (5)	0.5396 (4)	0.7362 (3)	0.0219 (10)
H15	0.0953	0.4958	0.7786	0.026*
C16	−0.0733 (5)	0.4593 (4)	0.6532 (3)	0.0250 (10)
H16	−0.0801	0.3591	0.6390	0.030*
C17	−0.1692 (5)	0.5217 (4)	0.5878 (3)	0.0224 (10)
C18	−0.1592 (5)	0.6684 (4)	0.6119 (3)	0.0222 (10)
H18	−0.2239	0.7125	0.5689	0.027*
C19	−0.0576 (5)	0.7516 (4)	0.6967 (3)	0.0224 (10)
H19	−0.0522	0.8518	0.7122	0.027*
C20	−0.2769 (5)	0.4302 (4)	0.4942 (3)	0.0288 (10)
H20A	−0.3691	0.3705	0.5174	0.043*
H20B	−0.2014	0.3703	0.4488	0.043*
H20C	−0.3302	0.4904	0.4557	0.043*
H1A	0.525 (5)	0.470 (4)	0.796 (3)	0.014 (10)*
O3	0.4546 (4)	0.3632 (3)	0.6655 (2)	0.0349 (8)
O4	0.2927 (4)	0.2835 (3)	0.7733 (2)	0.0319 (8)
N3	0.3338 (4)	0.2729 (3)	0.6806 (3)	0.0258 (8)
O5	0.2626 (4)	0.1803 (3)	0.6083 (2)	0.0346 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0123 (5)	0.0245 (6)	0.0255 (6)	0.0017 (4)	0.0065 (4)	0.0070 (4)
O1	0.0220 (16)	0.0240 (15)	0.0345 (19)	0.0057 (12)	0.0082 (14)	0.0020 (13)
O2	0.0183 (15)	0.0334 (17)	0.0247 (18)	−0.0012 (12)	0.0055 (13)	0.0132 (13)
N1	0.0161 (19)	0.022 (2)	0.030 (2)	0.0022 (15)	0.0065 (16)	0.0068 (17)
N2	0.0156 (11)	0.0195 (11)	0.0202 (11)	0.0022 (8)	0.0038 (8)	0.0057 (8)
C1	0.026 (2)	0.025 (2)	0.034 (3)	0.0112 (19)	0.008 (2)	0.015 (2)
C2	0.018 (2)	0.036 (3)	0.029 (3)	0.0085 (19)	0.005 (2)	0.018 (2)
C3	0.013 (2)	0.034 (3)	0.026 (3)	0.0035 (18)	0.0050 (18)	0.011 (2)
C4	0.019 (2)	0.022 (2)	0.031 (3)	0.0034 (17)	0.009 (2)	0.0079 (19)
C5	0.0084 (18)	0.019 (2)	0.030 (2)	0.0035 (15)	0.0100 (17)	0.0117 (17)
C6	0.013 (2)	0.022 (2)	0.028 (3)	0.0050 (16)	0.0076 (18)	0.0076 (18)
C7	0.012 (2)	0.024 (2)	0.034 (3)	0.0021 (17)	0.0049 (19)	0.0121 (19)
C8	0.012 (2)	0.020 (2)	0.030 (3)	0.0036 (16)	0.0044 (18)	0.0120 (18)
C9	0.021 (2)	0.023 (2)	0.033 (3)	0.0046 (18)	0.004 (2)	0.0118 (19)
C10	0.025 (2)	0.028 (2)	0.040 (3)	0.0091 (19)	0.016 (2)	0.020 (2)
C11	0.013 (2)	0.024 (2)	0.052 (3)	0.0042 (18)	0.010 (2)	0.019 (2)
C12	0.010 (2)	0.020 (2)	0.046 (3)	−0.0011 (16)	0.003 (2)	0.010 (2)
C13	0.018 (2)	0.025 (2)	0.029 (3)	0.0073 (18)	0.009 (2)	0.0077 (19)
C14	0.0093 (18)	0.024 (2)	0.023 (2)	0.0040 (15)	0.0103 (16)	0.0066 (17)
C15	0.015 (2)	0.026 (2)	0.028 (3)	0.0012 (17)	0.0058 (19)	0.0132 (19)
C16	0.024 (2)	0.020 (2)	0.033 (3)	−0.0006 (18)	0.009 (2)	0.0090 (19)
C17	0.010 (2)	0.033 (2)	0.026 (3)	0.0011 (17)	0.0111 (18)	0.0100 (19)
C18	0.010 (2)	0.033 (2)	0.028 (3)	0.0080 (17)	0.0102 (18)	0.0120 (19)
C19	0.015 (2)	0.023 (2)	0.032 (3)	0.0068 (17)	0.0122 (19)	0.0081 (19)
C20	0.019 (2)	0.034 (2)	0.031 (3)	−0.0003 (18)	0.007 (2)	0.005 (2)
O3	0.0331 (18)	0.0320 (17)	0.039 (2)	−0.0090 (14)	0.0143 (15)	0.0111 (14)
O4	0.0257 (17)	0.0449 (19)	0.0253 (19)	0.0004 (13)	0.0091 (14)	0.0092 (14)
N3	0.021 (2)	0.027 (2)	0.033 (2)	0.0045 (16)	0.0084 (17)	0.0113 (18)
O5	0.0264 (17)	0.0375 (18)	0.032 (2)	−0.0073 (14)	0.0016 (15)	−0.0019 (15)

Geometric parameters (Å, º) top

S1—O1	1.429 (3)	C9—H9	0.9500
S1—O2	1.431 (3)	C10—C11	1.376 (6)
S1—N2	1.652 (3)	C10—H10	0.9500
S1—C14	1.773 (4)	C11—C12	1.383 (6)
N1—C5	1.331 (5)	C11—H11	0.9500
N1—C1	1.362 (5)	C12—C13	1.384 (5)
N1—H1A	0.91 (4)	C12—H12	0.9500
N2—C7	1.478 (5)	C13—H13	0.9500
N2—C6	1.481 (4)	C14—C15	1.388 (5)
C1—C2	1.351 (6)	C14—C19	1.389 (5)
C1—H1	0.9500	C15—C16	1.358 (6)
C2—C3	1.384 (5)	C15—H15	0.9500
C2—H2	0.9500	C16—C17	1.406 (5)
C3—C4	1.385 (5)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.389 (5)
C4—C5	1.371 (6)	C17—C20	1.505 (6)
C4—H4	0.9500	C18—C19	1.380 (6)
C5—C6	1.507 (5)	C18—H18	0.9500
C6—H6A	0.9900	C19—H19	0.9500
C6—H6B	0.9900	C20—H20A	0.9800
C7—C8	1.512 (5)	C20—H20B	0.9800
C7—H7A	0.9900	C20—H20C	0.9800
C7—H7B	0.9900	O3—N3	1.275 (4)
C8—C13	1.384 (5)	O4—N3	1.258 (4)
C8—C9	1.388 (6)	N3—O5	1.217 (4)
C9—C10	1.398 (5)

O1—S1—O2	120.51 (18)	C8—C9—C10	120.1 (4)
O1—S1—N2	106.19 (16)	C8—C9—H9	119.9
O2—S1—N2	106.00 (16)	C10—C9—H9	119.9
O1—S1—C14	109.31 (17)	C11—C10—C9	119.8 (4)
O2—S1—C14	107.56 (17)	C11—C10—H10	120.1
N2—S1—C14	106.42 (17)	C9—C10—H10	120.1
C5—N1—C1	121.9 (4)	C10—C11—C12	120.2 (4)
C5—N1—H1A	125 (2)	C10—C11—H11	119.9
C1—N1—H1A	113 (2)	C12—C11—H11	119.9
C7—N2—C6	114.8 (3)	C11—C12—C13	120.0 (4)
C7—N2—S1	116.9 (2)	C11—C12—H12	120.0
C6—N2—S1	114.4 (2)	C13—C12—H12	120.0
C2—C1—N1	120.2 (4)	C8—C13—C12	120.5 (4)
C2—C1—H1	119.9	C8—C13—H13	119.7
N1—C1—H1	119.9	C12—C13—H13	119.7
C1—C2—C3	119.5 (4)	C15—C14—C19	120.8 (4)
C1—C2—H2	120.3	C15—C14—S1	120.0 (3)
C3—C2—H2	120.3	C19—C14—S1	119.1 (3)
C2—C3—C4	119.1 (4)	C16—C15—C14	119.7 (4)
C2—C3—H3	120.5	C16—C15—H15	120.1
C4—C3—H3	120.5	C14—C15—H15	120.1
C5—C4—C3	120.0 (4)	C15—C16—C17	121.2 (4)
C5—C4—H4	120.0	C15—C16—H16	119.4
C3—C4—H4	120.0	C17—C16—H16	119.4
N1—C5—C4	119.3 (4)	C18—C17—C16	118.0 (4)
N1—C5—C6	116.2 (4)	C18—C17—C20	121.9 (3)
C4—C5—C6	124.4 (3)	C16—C17—C20	120.1 (3)
N2—C6—C5	112.7 (3)	C19—C18—C17	121.5 (4)
N2—C6—H6A	109.1	C19—C18—H18	119.2
C5—C6—H6A	109.1	C17—C18—H18	119.2
N2—C6—H6B	109.1	C18—C19—C14	118.8 (4)
C5—C6—H6B	109.1	C18—C19—H19	120.6
H6A—C6—H6B	107.8	C14—C19—H19	120.6
N2—C7—C8	109.7 (3)	C17—C20—H20A	109.5
N2—C7—H7A	109.7	C17—C20—H20B	109.5
C8—C7—H7A	109.7	H20A—C20—H20B	109.5
N2—C7—H7B	109.7	C17—C20—H20C	109.5
C8—C7—H7B	109.7	H20A—C20—H20C	109.5
H7A—C7—H7B	108.2	H20B—C20—H20C	109.5
C13—C8—C9	119.3 (4)	O5—N3—O4	121.9 (4)
C13—C8—C7	119.8 (4)	O5—N3—O3	121.1 (4)
C9—C8—C7	120.8 (4)	O4—N3—O3	117.0 (4)

O1—S1—N2—C7	−47.2 (3)	C7—C8—C9—C10	−177.7 (3)
O2—S1—N2—C7	−176.5 (3)	C8—C9—C10—C11	0.7 (5)
C14—S1—N2—C7	69.2 (3)	C9—C10—C11—C12	−1.3 (5)
O1—S1—N2—C6	174.5 (3)	C10—C11—C12—C13	0.3 (6)
O2—S1—N2—C6	45.2 (3)	C9—C8—C13—C12	−1.8 (5)
C14—S1—N2—C6	−69.1 (3)	C7—C8—C13—C12	176.7 (3)
C5—N1—C1—C2	−1.0 (6)	C11—C12—C13—C8	1.3 (5)
N1—C1—C2—C3	−0.1 (6)	O1—S1—C14—C15	−151.3 (3)
C1—C2—C3—C4	0.7 (6)	O2—S1—C14—C15	−18.9 (4)
C2—C3—C4—C5	−0.2 (6)	N2—S1—C14—C15	94.4 (3)
C1—N1—C5—C4	1.5 (6)	O1—S1—C14—C19	34.0 (4)
C1—N1—C5—C6	179.7 (3)	O2—S1—C14—C19	166.4 (3)
C3—C4—C5—N1	−0.8 (6)	N2—S1—C14—C19	−80.3 (3)
C3—C4—C5—C6	−178.9 (4)	C19—C14—C15—C16	−0.9 (6)
C7—N2—C6—C5	140.3 (3)	S1—C14—C15—C16	−175.5 (3)
S1—N2—C6—C5	−80.4 (3)	C14—C15—C16—C17	1.5 (6)
N1—C5—C6—N2	141.3 (3)	C15—C16—C17—C18	−1.3 (6)
C4—C5—C6—N2	−40.5 (5)	C15—C16—C17—C20	178.0 (4)
C6—N2—C7—C8	−62.9 (4)	C16—C17—C18—C19	0.5 (6)
S1—N2—C7—C8	158.9 (3)	C20—C17—C18—C19	−178.7 (4)
N2—C7—C8—C13	−59.5 (4)	C17—C18—C19—C14	0.1 (6)
N2—C7—C8—C9	119.0 (4)	C15—C14—C19—C18	0.1 (6)
C13—C8—C9—C10	0.8 (5)	S1—C14—C19—C18	174.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.91 (4)	1.82 (4)	2.670 (5)	156 (3)
N1—H1A···O4	0.91 (4)	2.39 (4)	3.161 (5)	144 (3)
C6—H6B···O3	0.99	2.66	3.362 (5)	128
C15—H15···O4	0.95	2.68	3.493 (5)	144
C1—H1···O2ⁱ	0.95	2.71	3.315 (5)	122
C3—H3···O1ⁱⁱ	0.95	2.60	3.301 (5)	131
C20—H20A···O3ⁱⁱⁱ	0.98	2.43	3.256 (5)	142
C7—H7A···O4^iv	0.99	2.70	3.440 (5)	132
C11—H11···O4^v	0.95	2.54	3.439 (5)	158
C11—H11···O5^v	0.95	2.55	3.411 (5)	151
C20—H20C···O3^vi	0.98	2.62	3.594 (5)	174
C10—H10···O5^vii	0.95	2.66	3.309 (6)	126

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁N₂O₂S⁺·NO₃⁻
M_r	415.46
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	7.6852 (15), 9.811 (2), 13.240 (3)
α, β, γ (°)	104.26 (3), 91.82 (3), 95.64 (2)
V (Å³)	961.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.960, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	7087, 3355, 2020
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.188, 0.94
No. of reflections	3355
No. of parameters	267
No. of restraints	18
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.73

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.91 (4)	1.82 (4)	2.670 (5)	156 (3)
N1—H1A···O4	0.91 (4)	2.39 (4)	3.161 (5)	144 (3)
C6—H6B···O3	0.99	2.66	3.362 (5)	128
C15—H15···O4	0.95	2.68	3.493 (5)	144
C1—H1···O2ⁱ	0.95	2.71	3.315 (5)	122
C3—H3···O1ⁱⁱ	0.95	2.60	3.301 (5)	131
C20—H20A···O3ⁱⁱⁱ	0.98	2.43	3.256 (5)	142
C7—H7A···O4^iv	0.99	2.70	3.440 (5)	132
C11—H11···O4^v	0.95	2.54	3.439 (5)	158
C11—H11···O5^v	0.95	2.55	3.411 (5)	151
C20—H20C···O3^vi	0.98	2.62	3.594 (5)	174
C10—H10···O5^vii	0.95	2.66	3.309 (6)	126

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

Acknowledgements

This project was supported by the Changsha University of Science and Technology Talent Fund (project No. 1004214)

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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