5,13-Disulfamoyl-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10,12,14-hexaen-1-ium chloride

Xu, Y.; Jin, S.; Zhu, J.; Liu, Y.J.; Shi, C.C.

doi:10.1107/S1600536811038189

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2730

https://doi.org/10.1107/S1600536811038189

Open

access

5,13-Disulfamoyl-1,9-diazatetracyclo[7.7.1.0^2,7.0^10,15]heptadeca-2(7),3,5,10,12,14-hexaen-1-ium chloride

Yichao Xu,^a Shouwen Jin,^a ^* Jianlong Zhu,^a YingJia Liu ^a and ChuanChuan Shi ^a

^aTianmu College of ZheJiang A & F University, Lin'An 311300, People's Republic of China
^*Correspondence e-mail: JINSWw@yahoo.cn

(Received 31 August 2011; accepted 19 September 2011; online 30 September 2011)

In the title salt, C₁₅H₁₇N₄O₄S₂⁺·Cl⁻, the chloride anion is disordered over two positions with occupancies of 0.776 (6) and 0.224 (6). The cation adopts an L shape and the dihedral angle between the benzene rings is 82.5 (3)°. In the crystal, inversion dimers of cations linked by pairs of N—H⋯N hydrogen bonds occur, with the bond arising from the protonated N atom. The cationic dimers are linked into chains via the disordered chloride ions by way of N—H⋯Cl hydrogen bonds and N—H⋯O, C—H⋯O and C—H⋯Cl interactions also occur, which help to consolidate the three-dimensional network.

Related literature

For a related structure and background references to supramolecular networks, see: Jin et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₇N₄O₄S₂⁺·Cl⁻
M_r = 416.90
Monoclinic, P 2₁ /c
a = 11.5247 (11) Å
b = 18.5693 (16) Å
c = 8.1489 (7) Å
β = 109.177 (1)°
V = 1647.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 298 K
0.40 × 0.33 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.815, T_max = 0.869
8082 measured reflections
2895 independent reflections
1944 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.219
S = 1.08
2895 reflections
239 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.96 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.89	2.26	3.081 (8)	153
N1—H1B⋯Cl1ⁱⁱ	0.89	2.26	3.141 (7)	170
N2—H2A⋯Cl1ⁱⁱⁱ	0.89	2.19	3.042 (6)	160
N2—H2B⋯O1^iv	0.89	2.46	3.109 (7)	130
N2—H2B⋯O2^iv	0.89	2.36	3.240 (7)	168
N4—H4⋯N2^v	0.91	2.02	2.922 (7)	173
C12—H12⋯O3^vi	0.93	2.49	3.416 (7)	175
C13—H13A⋯Cl1^vii	0.97	2.76	3.514 (7)	135
C14—H14A⋯O4ⁱ	0.97	2.50	3.212 (9)	130
C15—H15A⋯O3^viii	0.97	2.52	3.443 (7)	158
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) -x+1, -y+1, -z+1; (vi) -x+1, -y+1, -z+2; (vii) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (viii) x, y, z-1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811038189/hb6395sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038189/hb6395Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811038189/hb6395Isup3.cml

checkCIF report

Comment top

Organic salts based on hydrogen bonding are a research field receiving great attention in recent years. As an extension of our study concentrating on hydrogen bonded assembly of organic acid and organic base (Jin et al., 2010), herein we report the crystal structure of 2,9-Dibenzenesulfonamide-1,5-diazaium-bicyclo[3.3.1]dimethanodibenzo chloride.

The crystal of the title compound of the formula C₁₅H₁₇ClN₄O₄S₂ was obtained by recrystallization of 2,9-Dibenzenesulfonamide-1,5-diazaium- bicyclo[3.3.1]dimethanodibenzo from methanol and HCl solution.

The compound is a salt. The asymmetric unit of the compound consists of one monocation, and one chloride anion (Fig. 1), respectively.

The chloride anion is disordered over two positions with occupancies of 0.78, and 0.22 respectively. In the compound there is a mirror plane running through the C15 atom. Two cations formed dimers via the N—H···N hydrogen bond between the NH₊ cation and the amino group with N—N separation of 2.922 (6) A%. The cation dimers were connected together via the chloride anion through CH—Cl, Cl—O, and N—H···Cl contacts to form one-dimensional chain (A) running along the b axis direction (Fig. 2). Such adjacent chains were combined together by the CH₂—O, and CH—O interactions to form two-dimensional sheet extending along the bc plane. Such kind of sheets were stacked along the a axis direction via the CH2—Cl interactions to form three-dimensional network structure. It is worthy to note that there are one-dimensional chains (B) that are running through the three-dimensional network. And such kind of chains were connected with the three-dimensional network through the N—H···S, and N—H···O interactions.

Related literature top

For a related structure and background references to supramolecular networks, see: Jin et al. (2010).

Experimental top

A solution of 2,9-dibenzenesulfonamide-1,5-diazabicyclo[3.3.1]dimethanodibenzo (38 mg, 0.1 mmol) was dissolved in 5 ml of methanol and 1 ml of conc. HCl under continuous stirring. The solution was stirred for about 1 h at room temperature, then the solution was filtered into a test tube. The solution was left standing at room temperature for several days, colorless block crystals were isolated after slow evaporation of the solution in air at ambient temperature. The crystals were collected and dried in air to give the title compound.

Structure description top

The compound is a salt. The asymmetric unit of the compound consists of one monocation, and one chloride anion (Fig. 1), respectively.

For a related structure and background references to supramolecular networks, see: Jin et al. (2010).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The one-dimensional doublechain formed through CH—O, and CH₂—O interactions running along the a axis direction.

5,13-Disulfamoyl-1,9-diazatetracyclo[7.7.1.0^2,7.0^10,15]heptadeca- 2(7),3,5,10,12,14-hexaen-1-ium chloride top

Crystal data top

C₁₅H₁₇N₄O₄S₂⁺·Cl⁻	Z = 4
M_r = 416.90	F(000) = 864
Monoclinic, P2₁/c	D_x = 1.681 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.5247 (11) Å	µ = 0.52 mm⁻¹
b = 18.5693 (16) Å	T = 298 K
c = 8.1489 (7) Å	Block, colorless
β = 109.177 (1)°	0.40 × 0.33 × 0.27 mm
V = 1647.1 (3) Å³

Data collection top

Bruker SMART CCD diffractometer	2895 independent reflections
Radiation source: fine-focus sealed tube	1944 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
phi and ω scans	θ_max = 25.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→13
T_min = 0.815, T_max = 0.869	k = −21→22
8082 measured reflections	l = −9→5

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.219	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0953P)² + 5.3108P] where P = (F_o² + 2F_c²)/3
2895 reflections	(Δ/σ)_max < 0.001
239 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.96 e Å⁻³

Crystal data top

C₁₅H₁₇N₄O₄S₂⁺·Cl⁻	V = 1647.1 (3) Å³
M_r = 416.90	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5247 (11) Å	µ = 0.52 mm⁻¹
b = 18.5693 (16) Å	T = 298 K
c = 8.1489 (7) Å	0.40 × 0.33 × 0.27 mm
β = 109.177 (1)°

Data collection top

Bruker SMART CCD diffractometer	2895 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1944 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.869	R_int = 0.042
8082 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.219	H-atom parameters constrained
S = 1.08	Δρ_max = 0.52 e Å⁻³
2895 reflections	Δρ_min = −0.96 e Å⁻³
239 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	Occ. (<1)
Cl1	0.1069 (3)	0.02872 (18)	0.3829 (5)	0.0948 (11)	0.776 (6)
Cl1'	0.0764 (12)	0.0213 (7)	0.4728 (19)	0.0948 (11)	0.224 (6)
N1	1.2145 (4)	0.1555 (3)	0.6436 (7)	0.0489 (13)
H1A	1.2289	0.1965	0.5969	0.073*
H1B	1.1813	0.1236	0.5598	0.073*
N2	0.2583 (4)	0.4134 (3)	0.6686 (6)	0.0436 (12)
H2A	0.2080	0.4192	0.7302	0.065*
H2B	0.2262	0.3815	0.5843	0.065*
N3	0.6862 (4)	0.3219 (2)	0.2614 (5)	0.0342 (10)
N4	0.7476 (4)	0.4335 (2)	0.4164 (6)	0.0350 (10)
H4	0.7507	0.4818	0.3997	0.042*
O1	1.0815 (4)	0.1016 (2)	0.7888 (6)	0.0581 (12)
O2	1.1807 (4)	0.2171 (3)	0.8899 (6)	0.0684 (14)
O3	0.4230 (4)	0.4292 (3)	0.9437 (5)	0.0658 (14)
O4	0.3793 (6)	0.3081 (3)	0.8158 (8)	0.0860 (18)
S1	1.12094 (13)	0.17065 (8)	0.74765 (18)	0.0425 (4)
S2	0.38898 (14)	0.38395 (8)	0.79416 (19)	0.0440 (4)
C1	0.9909 (5)	0.2165 (3)	0.6090 (7)	0.0349 (12)
C2	0.9842 (5)	0.2910 (3)	0.6153 (7)	0.0356 (12)
H2	1.0470	0.3169	0.6947	0.043*
C3	0.8829 (4)	0.3271 (3)	0.5022 (7)	0.0325 (11)
C4	0.7906 (4)	0.2870 (3)	0.3842 (6)	0.0318 (11)
C5	0.7975 (5)	0.2124 (3)	0.3834 (7)	0.0361 (12)
H5	0.7337	0.1861	0.3071	0.043*
C6	0.8967 (5)	0.1769 (3)	0.4933 (7)	0.0381 (12)
H6	0.9011	0.1270	0.4907	0.046*
C7	0.4950 (5)	0.3985 (3)	0.6817 (7)	0.0336 (12)
C8	0.4905 (4)	0.3543 (3)	0.5427 (7)	0.0328 (11)
H8	0.4314	0.3183	0.5080	0.039*
C9	0.5745 (4)	0.3639 (3)	0.4549 (6)	0.0288 (11)
C10	0.6603 (4)	0.4199 (3)	0.5082 (6)	0.0301 (11)
C11	0.6638 (5)	0.4636 (3)	0.6472 (7)	0.0371 (12)
H11	0.7223	0.5000	0.6815	0.045*
C12	0.5815 (5)	0.4538 (3)	0.7349 (7)	0.0394 (13)
H12	0.5833	0.4834	0.8278	0.047*
C13	0.8742 (5)	0.4079 (3)	0.5131 (8)	0.0394 (13)
H13A	0.8962	0.4223	0.6339	0.047*
H13B	0.9320	0.4302	0.4648	0.047*
C14	0.5740 (5)	0.3144 (3)	0.3071 (7)	0.0352 (12)
H14A	0.5664	0.2649	0.3404	0.042*
H14B	0.5034	0.3254	0.2062	0.042*
C15	0.7088 (5)	0.3973 (3)	0.2424 (7)	0.0421 (13)
H15A	0.6348	0.4199	0.1664	0.051*
H15B	0.7728	0.4026	0.1901	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.093 (2)	0.091 (2)	0.107 (3)	−0.0023 (16)	0.0411 (18)	−0.0070 (19)
Cl1'	0.093 (2)	0.091 (2)	0.107 (3)	−0.0023 (16)	0.0411 (18)	−0.0070 (19)
N1	0.041 (3)	0.047 (3)	0.063 (3)	0.006 (2)	0.023 (2)	0.008 (2)
N2	0.046 (3)	0.049 (3)	0.037 (3)	−0.004 (2)	0.015 (2)	−0.007 (2)
N3	0.035 (2)	0.038 (2)	0.031 (2)	0.0010 (19)	0.0125 (18)	−0.0018 (19)
N4	0.037 (2)	0.027 (2)	0.043 (2)	−0.0031 (18)	0.016 (2)	0.0048 (19)
O1	0.061 (3)	0.058 (3)	0.058 (3)	0.007 (2)	0.023 (2)	0.023 (2)
O2	0.063 (3)	0.072 (3)	0.056 (3)	0.017 (2)	−0.001 (2)	−0.014 (2)
O3	0.051 (3)	0.113 (4)	0.034 (2)	0.005 (3)	0.015 (2)	−0.011 (2)
O4	0.115 (4)	0.051 (3)	0.127 (5)	0.026 (3)	0.087 (4)	0.040 (3)
S1	0.0381 (8)	0.0485 (9)	0.0396 (8)	0.0072 (6)	0.0111 (6)	0.0007 (6)
S2	0.0533 (9)	0.0450 (9)	0.0411 (8)	0.0103 (7)	0.0256 (7)	0.0109 (6)
C1	0.030 (3)	0.038 (3)	0.039 (3)	0.002 (2)	0.015 (2)	−0.001 (2)
C2	0.030 (3)	0.038 (3)	0.041 (3)	−0.006 (2)	0.013 (2)	−0.007 (2)
C3	0.030 (3)	0.035 (3)	0.037 (3)	−0.001 (2)	0.019 (2)	−0.003 (2)
C4	0.030 (3)	0.037 (3)	0.032 (3)	0.000 (2)	0.014 (2)	−0.003 (2)
C5	0.028 (3)	0.040 (3)	0.039 (3)	−0.001 (2)	0.010 (2)	−0.010 (2)
C6	0.041 (3)	0.031 (3)	0.047 (3)	−0.002 (2)	0.020 (3)	−0.005 (2)
C7	0.036 (3)	0.034 (3)	0.033 (3)	0.009 (2)	0.015 (2)	0.004 (2)
C8	0.027 (3)	0.033 (3)	0.035 (3)	0.003 (2)	0.007 (2)	0.001 (2)
C9	0.026 (2)	0.028 (3)	0.030 (3)	0.006 (2)	0.005 (2)	0.002 (2)
C10	0.030 (3)	0.026 (3)	0.031 (3)	0.006 (2)	0.005 (2)	0.004 (2)
C11	0.041 (3)	0.027 (3)	0.041 (3)	−0.004 (2)	0.011 (2)	−0.005 (2)
C12	0.049 (3)	0.035 (3)	0.033 (3)	0.007 (2)	0.012 (2)	−0.004 (2)
C13	0.031 (3)	0.035 (3)	0.052 (3)	−0.003 (2)	0.013 (2)	0.000 (2)
C14	0.030 (3)	0.039 (3)	0.034 (3)	−0.002 (2)	0.007 (2)	−0.007 (2)
C15	0.047 (3)	0.048 (3)	0.036 (3)	0.003 (3)	0.020 (3)	0.007 (3)

Geometric parameters (Å, º) top

Cl1'—Cl1'ⁱ	2.11 (3)	C2—H2	0.9300
N1—S1	1.600 (5)	C3—C4	1.392 (7)
N1—H1A	0.8900	C3—C13	1.509 (7)
N1—H1B	0.8900	C4—C5	1.388 (7)
N2—S2	1.613 (5)	C5—C6	1.367 (7)
N2—H2A	0.8900	C5—H5	0.9300
N2—H2B	0.8900	C6—H6	0.9300
N3—C15	1.441 (7)	C7—C8	1.386 (7)
N3—C4	1.442 (6)	C7—C12	1.397 (8)
N3—C14	1.465 (6)	C8—C9	1.391 (7)
N4—C10	1.460 (6)	C8—H8	0.9300
N4—C13	1.490 (7)	C9—C10	1.401 (7)
N4—C15	1.499 (7)	C9—C14	1.513 (7)
N4—H4	0.9100	C10—C11	1.384 (7)
O1—S1	1.437 (5)	C11—C12	1.375 (7)
O2—S1	1.427 (5)	C11—H11	0.9300
O3—S2	1.425 (5)	C12—H12	0.9300
O4—S2	1.428 (5)	C13—H13A	0.9700
S1—C1	1.770 (5)	C13—H13B	0.9700
S2—C7	1.772 (5)	C14—H14A	0.9700
C1—C2	1.387 (7)	C14—H14B	0.9700
C1—C6	1.392 (7)	C15—H15A	0.9700
C2—C3	1.398 (7)	C15—H15B	0.9700

S1—N1—H1A	109.3	C4—C5—H5	119.5
S1—N1—H1B	109.2	C5—C6—C1	119.2 (5)
H1A—N1—H1B	109.5	C5—C6—H6	120.4
S2—N2—H2A	109.2	C1—C6—H6	120.4
S2—N2—H2B	109.2	C8—C7—C12	121.3 (5)
H2A—N2—H2B	109.5	C8—C7—S2	119.1 (4)
C15—N3—C4	111.8 (4)	C12—C7—S2	119.6 (4)
C15—N3—C14	109.0 (4)	C7—C8—C9	120.0 (5)
C4—N3—C14	112.7 (4)	C7—C8—H8	120.0
C10—N4—C13	113.2 (4)	C9—C8—H8	120.0
C10—N4—C15	111.4 (4)	C8—C9—C10	118.3 (4)
C13—N4—C15	107.1 (4)	C8—C9—C14	120.7 (4)
C10—N4—H4	108.3	C10—C9—C14	121.0 (4)
C13—N4—H4	108.3	C11—C10—C9	121.2 (5)
C15—N4—H4	108.3	C11—C10—N4	118.5 (4)
O2—S1—O1	117.1 (3)	C9—C10—N4	120.3 (4)
O2—S1—N1	107.9 (3)	C12—C11—C10	120.5 (5)
O1—S1—N1	106.7 (3)	C12—C11—H11	119.8
O2—S1—C1	108.0 (3)	C10—C11—H11	119.8
O1—S1—C1	108.2 (3)	C11—C12—C7	118.7 (5)
N1—S1—C1	108.8 (3)	C11—C12—H12	120.6
O3—S2—O4	119.1 (3)	C7—C12—H12	120.6
O3—S2—N2	106.3 (3)	N4—C13—C3	111.0 (4)
O4—S2—N2	108.5 (3)	N4—C13—H13A	109.4
O3—S2—C7	108.0 (3)	C3—C13—H13A	109.4
O4—S2—C7	108.0 (3)	N4—C13—H13B	109.4
N2—S2—C7	106.2 (2)	C3—C13—H13B	109.4
C2—C1—C6	120.7 (5)	H13A—C13—H13B	108.0
C2—C1—S1	120.1 (4)	N3—C14—C9	111.8 (4)
C6—C1—S1	119.1 (4)	N3—C14—H14A	109.3
C1—C2—C3	119.9 (5)	C9—C14—H14A	109.3
C1—C2—H2	120.1	N3—C14—H14B	109.3
C3—C2—H2	120.1	C9—C14—H14B	109.3
C4—C3—C2	118.9 (5)	H14A—C14—H14B	107.9
C4—C3—C13	121.5 (5)	N3—C15—N4	110.0 (4)
C2—C3—C13	119.6 (5)	N3—C15—H15A	109.7
C5—C4—C3	120.3 (5)	N4—C15—H15A	109.7
C5—C4—N3	118.8 (4)	N3—C15—H15B	109.7
C3—C4—N3	120.9 (5)	N4—C15—H15B	109.7
C6—C5—C4	121.0 (5)	H15A—C15—H15B	108.2
C6—C5—H5	119.5

O2—S1—C1—C2	20.7 (5)	C12—C7—C8—C9	1.1 (7)
O1—S1—C1—C2	148.3 (4)	S2—C7—C8—C9	−178.7 (4)
N1—S1—C1—C2	−96.2 (5)	C7—C8—C9—C10	−1.5 (7)
O2—S1—C1—C6	−159.9 (4)	C7—C8—C9—C14	177.7 (5)
O1—S1—C1—C6	−32.2 (5)	C8—C9—C10—C11	1.5 (7)
N1—S1—C1—C6	83.3 (5)	C14—C9—C10—C11	−177.7 (5)
C6—C1—C2—C3	−1.2 (8)	C8—C9—C10—N4	−178.0 (4)
S1—C1—C2—C3	178.2 (4)	C14—C9—C10—N4	2.8 (7)
C1—C2—C3—C4	−0.3 (7)	C13—N4—C10—C11	76.1 (6)
C1—C2—C3—C13	178.2 (5)	C15—N4—C10—C11	−163.2 (5)
C2—C3—C4—C5	2.1 (7)	C13—N4—C10—C9	−104.4 (5)
C13—C3—C4—C5	−176.4 (5)	C15—N4—C10—C9	16.4 (6)
C2—C3—C4—N3	−178.1 (4)	C9—C10—C11—C12	−1.0 (8)
C13—C3—C4—N3	3.4 (7)	N4—C10—C11—C12	178.5 (5)
C15—N3—C4—C5	−162.8 (4)	C10—C11—C12—C7	0.5 (8)
C14—N3—C4—C5	74.0 (6)	C8—C7—C12—C11	−0.5 (8)
C15—N3—C4—C3	17.5 (6)	S2—C7—C12—C11	179.3 (4)
C14—N3—C4—C3	−105.8 (5)	C10—N4—C13—C3	75.6 (5)
C3—C4—C5—C6	−2.5 (8)	C15—N4—C13—C3	−47.6 (5)
N3—C4—C5—C6	177.7 (5)	C4—C3—C13—N4	13.2 (7)
C4—C5—C6—C1	1.0 (8)	C2—C3—C13—N4	−165.3 (4)
C2—C1—C6—C5	0.9 (8)	C15—N3—C14—C9	−48.8 (5)
S1—C1—C6—C5	−178.6 (4)	C4—N3—C14—C9	76.0 (5)
O3—S2—C7—C8	172.3 (4)	C8—C9—C14—N3	−166.0 (4)
O4—S2—C7—C8	42.2 (5)	C10—C9—C14—N3	13.3 (6)
N2—S2—C7—C8	−74.1 (5)	C4—N3—C15—N4	−54.7 (5)
O3—S2—C7—C12	−7.5 (5)	C14—N3—C15—N4	70.6 (5)
O4—S2—C7—C12	−137.6 (5)	C10—N4—C15—N3	−52.9 (6)
N2—S2—C7—C12	106.1 (4)	C13—N4—C15—N3	71.4 (5)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱⁱ	0.89	2.26	3.081 (8)	153
N1—H1B···Cl1ⁱⁱⁱ	0.89	2.26	3.141 (7)	170
N2—H2A···Cl1^iv	0.89	2.19	3.042 (6)	160
N2—H2B···O1^v	0.89	2.46	3.109 (7)	130
N2—H2B···O2^v	0.89	2.36	3.240 (7)	168
N4—H4···N2^vi	0.91	2.02	2.922 (7)	173
C12—H12···O3^vii	0.93	2.49	3.416 (7)	175
C13—H13A···Cl1^viii	0.97	2.76	3.514 (7)	135
C14—H14A···O4ⁱⁱ	0.97	2.50	3.212 (9)	130
C15—H15A···O3^ix	0.97	2.52	3.443 (7)	158

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇N₄O₄S₂⁺·Cl⁻
M_r	416.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.5247 (11), 18.5693 (16), 8.1489 (7)
β (°)	109.177 (1)
V (Å³)	1647.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.40 × 0.33 × 0.27

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.815, 0.869
No. of measured, independent and observed [I > 2σ(I)] reflections	8082, 2895, 1944
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.219, 1.08
No. of reflections	2895
No. of parameters	239
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.96

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.89	2.26	3.081 (8)	153
N1—H1B···Cl1ⁱⁱ	0.89	2.26	3.141 (7)	170
N2—H2A···Cl1ⁱⁱⁱ	0.89	2.19	3.042 (6)	160
N2—H2B···O1^iv	0.89	2.46	3.109 (7)	130
N2—H2B···O2^iv	0.89	2.36	3.240 (7)	168
N4—H4···N2^v	0.91	2.02	2.922 (7)	173
C12—H12···O3^vi	0.93	2.49	3.416 (7)	175
C13—H13A···Cl1^vii	0.97	2.76	3.514 (7)	135
C14—H14A···O4ⁱ	0.97	2.50	3.212 (9)	130
C15—H15A···O3^viii	0.97	2.52	3.443 (7)	158

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

Acknowledgements

We gratefully acknowledge financial support by the Education Office Foundation of Zhejiang Province (project No. Y201017321) and the innovation project of Zhejiang A & F University.

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jin, S. W., Zhang, W. B., Liu, L., Gao, H. F., Wang, D. Q., Chen, R. P. & Xu, X. L. (2010). J. Mol. Struct. 975, 128–136. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.