4,4′-Bipyridine–4-(p-toluene­sulfonamido)­benzoic acid (1/2)

Huang, M.-L.

doi:10.1107/S1600536811034544

organic compounds

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Volume 67| Part 9| September 2011| Page o2495

doi:10.1107/S1600536811034544

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4,4′-Bipyridine–4-(p-toluenesulfonamido)benzoic acid (1/2)

Miao-Ling Huang ^a ^*

^aCollege of Chemistry and Life Sciences, Quanzhou Normal University, Fujian 362000, People's Republic of China
^*Correspondence e-mail: hml301@163.com

(Received 18 August 2011; accepted 22 August 2011; online 27 August 2011)

In the title compound, C₁₄H₁₃NO₄S·0.5C₁₀H₈N₂, the two benzene rings are nearly perpendicular to each other [dihedral angle = 83.21 (10)°]. The bipyridine molecule is centrosymmetric, the mid-point of the C—C bond linking the pyridine rings being located on an inversion center. Intermolecular N—H⋯O and O—H⋯N hydrogen bonds and weak intermolecular C—H⋯O hydrogen bonds are present in the crystal structure.

Related literature

For the background to the compound, see: Antolini et al. (1984 ); Menabue & Saladini (1988 ).

Experimental

Crystal data

C₁₄H₁₃NO₄S·0.5C₁₀H₈N₂
M_r = 369.41
Monoclinic, P 2₁ /n
a = 5.8732 (7) Å
b = 8.124 (1) Å
c = 36.806 (5) Å
β = 94.137 (2)°
V = 1751.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.39 × 0.24 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.922, T_max = 0.957
7704 measured reflections
3234 independent reflections
2255 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.107
S = 0.99
3234 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.03	2.861 (2)	162
O2—H2A⋯N2ⁱⁱ	0.82	1.87	2.691 (2)	175
C2—H2⋯O4ⁱⁱ	0.93	2.51	3.413 (2)	163
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034544/xu5301sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034544/xu5301Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034544/xu5301Isup3.cml

checkCIF report

Comment top

N-Protected amino acids possess R-CONH-R' group analogous to the structure of O-terminal of peptide and proteins (Menabue & Saladini, 1988, Antolini et al., 1984). The substitution of an Ar—SO₂-group on amine makes the 4-aminobenzeoic acid increase the coordination donors to three types-O, N donors from carboxyl, sulfoxyl and amine respectively, which may result in different coordination mode. In this paper, we attempt synthesizing the N-p-tolysulfonyl-4-amionbenzoic acid adduct of Erbium and 4,4'-bipyridine, but the result to get the title compound.

The title compound contains of one N-p-tolysulfonyl-4-amionbenzoic acid molecule and one 4,4'-bipyridine in the asymmetric unit (Fig.1). The molecule has a C4—N1—S1—C8 of 74.247 (2) °, and the dihedral angle between the benzene rings is 83.213 (6) °. There exit intermolecular hydrogen bonds between carboxylate group oxygen atoms, secondary amine nitrogen atoms and pyridine ring nitrogen atoms of N—H···O and O—H···N. Then, an extended one-dimensional chain structure along b axis is formed (Fig.2). It is interesting that the hydrogen bonds play an important role in forming the one-dimensional structure and stabilize the superamolecular structure(Fig.3).

Related literature top

For the background to the compound, see: Antolini et al. (1984); Menabue & Saladini (1988).

Experimental top

A mixture of N-p-tolysulfonylchloride (1 mmol) and 4-amionbenzoic acid (1 mmol) in water (20 mL) was stirred at room temperature for 10 h. Then HCl (12 mol/L) was slowly added to the resulting solution. The mixture was stirred for 5 min and filtrated. The precipitate was washed by distilled water, and dried to constant heavy [product 1].

To a solution of the product 1 (1 mmol) in water-DMF 1:1 (10 mL), an aqueous solution (5 ml) of Er(NO₃)₃.6H₂O (0.5 mmol) and a solution of 4,4'-bipyridine (0.25 mmol) in ethanol (95%, 5 ml) was added. After refluxing for 12 h at 343 K, the mixture was filtered off while hot. The block colourless single crystals suitable for X-ray analysis were obtained by slow evaporation of the filtrate at room temperature after one week.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The ORTEP drawing of the title compound (I). Displacement ellipsoids are drawn at 30% probability level. All hydrogen atams have been omitted for reasons of clarity.
	Fig. 2. A view of the hydrogen bonds (dotted lines) in the crystal structure of the title compound (I).
	Fig. 3. The crystal packing of the title compound (I), viewed along the c axis.

4,4'-Bipyridine–4-(p-toluenesulfonamido)benzoic acid (1/2) top

Crystal data top

C₁₄H₁₃NO₄S·0.5C₁₀H₈N₂	F(000) = 772
M_r = 369.41	D_x = 1.401 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2422 reflections
a = 5.8732 (7) Å	θ = 2.6–23.6°
b = 8.124 (1) Å	µ = 0.21 mm⁻¹
c = 36.806 (5) Å	T = 296 K
β = 94.137 (2)°	Block, colourless
V = 1751.6 (4) Å³	0.39 × 0.24 × 0.21 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3234 independent reflections
Radiation source: fine-focus sealed tube	2255 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→7
T_min = 0.922, T_max = 0.957	k = −9→7
7704 measured reflections	l = −44→44

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0567P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
3234 reflections	Δρ_max = 0.21 e Å⁻³
237 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0079 (11)

Crystal data top

C₁₄H₁₃NO₄S·0.5C₁₀H₈N₂	V = 1751.6 (4) Å³
M_r = 369.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.8732 (7) Å	µ = 0.21 mm⁻¹
b = 8.124 (1) Å	T = 296 K
c = 36.806 (5) Å	0.39 × 0.24 × 0.21 mm
β = 94.137 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3234 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2255 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.957	R_int = 0.026
7704 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 0.99	Δρ_max = 0.21 e Å⁻³
3234 reflections	Δρ_min = −0.24 e Å⁻³
237 parameters

Special details top

Experimental. IR(KBr): 3439(s), 3214(versus), 2493(w), 1922(w), 1668(s), 1603(versus), 1511 (w), 1477(vw), 1409(m), 1341(s), 1314(s), 1289(s), 1232(m), 1216(m), 1158(versus), 1092(versus), 1004(m), 923(m), 860(m), 803(m), 779(m), 699(m), 668(m), 626(s), 574(s), 548(s), 521(s), 502(m)cm^-1.

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)
C1	0.5273 (3)	1.1613 (2)	0.09831 (5)	0.0455 (5)
C2	0.3358 (4)	1.1518 (2)	0.11792 (6)	0.0572 (6)
H2	0.2583	1.2478	0.1232	0.069*
C3	0.2574 (4)	1.0027 (3)	0.12985 (6)	0.0571 (6)
H3	0.1270	0.9983	0.1427	0.069*
C4	0.3736 (3)	0.8592 (2)	0.12256 (5)	0.0450 (5)
C5	0.5699 (3)	0.8680 (2)	0.10403 (5)	0.0495 (5)
H5	0.6516	0.7727	0.0998	0.059*
C6	0.6449 (3)	1.0172 (2)	0.09175 (5)	0.0495 (5)
H6	0.7756	1.0215	0.0789	0.059*
C7	0.5983 (4)	1.3224 (3)	0.08396 (6)	0.0544 (5)
C8	0.3248 (3)	0.6500 (2)	0.20402 (5)	0.0432 (5)
C9	0.5294 (3)	0.5665 (2)	0.20487 (6)	0.0569 (6)
H9	0.5745	0.5147	0.1840	0.068*
C10	0.6658 (4)	0.5605 (3)	0.23665 (7)	0.0622 (6)
H10	0.8045	0.5052	0.2370	0.075*
C11	0.6024 (4)	0.6350 (3)	0.26843 (6)	0.0558 (6)
C12	0.3979 (4)	0.7180 (3)	0.26679 (6)	0.0606 (6)
H12	0.3521	0.7696	0.2876	0.073*
C13	0.2597 (3)	0.7264 (2)	0.23507 (6)	0.0541 (5)
H13	0.1223	0.7836	0.2346	0.065*
C14	0.7556 (4)	0.6262 (3)	0.30290 (7)	0.0854 (8)
H14A	0.8893	0.5632	0.2986	0.128*	0.50
H14B	0.6755	0.5743	0.3217	0.128*	0.50
H14C	0.7997	0.7354	0.3105	0.128*	0.50
H14D	0.6870	0.6854	0.3219	0.128*	0.50
H14E	0.9008	0.6743	0.2988	0.128*	0.50
H14F	0.7766	0.5132	0.3100	0.128*	0.50
C15	0.7243 (5)	0.6866 (3)	0.00908 (8)	0.0912 (9)
H15	0.5864	0.6378	0.0011	0.109*
C16	0.7715 (4)	0.8401 (3)	−0.00428 (7)	0.0784 (8)
H16	0.6671	0.8914	−0.0208	0.094*
C17	0.9707 (3)	0.9168 (2)	0.00662 (5)	0.0447 (5)
C18	1.1119 (4)	0.8311 (3)	0.03098 (6)	0.0745 (7)
H18	1.2501	0.8772	0.0397	0.089*
C19	1.0513 (5)	0.6771 (3)	0.04270 (7)	0.0818 (8)
H19	1.1528	0.6220	0.0590	0.098*
N1	0.2922 (3)	0.70046 (19)	0.13109 (4)	0.0559 (5)
H1	0.3281	0.6224	0.1168	0.067*
N2	0.8605 (4)	0.6044 (2)	0.03226 (5)	0.0681 (5)
O1	0.5113 (3)	1.45211 (18)	0.09093 (5)	0.0797 (5)
O2	0.7586 (3)	1.31137 (17)	0.06109 (5)	0.0780 (5)
H2A	0.7877	1.4033	0.0535	0.117*
O3	−0.0355 (2)	0.76526 (18)	0.16802 (4)	0.0655 (4)
O4	0.0804 (3)	0.47892 (17)	0.15660 (4)	0.0686 (5)
S1	0.14014 (9)	0.64661 (6)	0.164306 (13)	0.05199 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0551 (12)	0.0388 (12)	0.0428 (10)	0.0030 (9)	0.0042 (9)	0.0038 (9)
C2	0.0691 (14)	0.0414 (13)	0.0628 (13)	0.0050 (11)	0.0161 (11)	−0.0028 (10)
C3	0.0639 (14)	0.0463 (13)	0.0638 (14)	0.0018 (11)	0.0220 (11)	0.0019 (10)
C4	0.0599 (12)	0.0394 (11)	0.0357 (10)	0.0014 (10)	0.0032 (9)	0.0032 (8)
C5	0.0593 (12)	0.0385 (12)	0.0507 (11)	0.0077 (10)	0.0053 (10)	0.0044 (9)
C6	0.0541 (12)	0.0481 (13)	0.0470 (11)	0.0033 (10)	0.0093 (9)	0.0035 (9)
C7	0.0638 (14)	0.0444 (13)	0.0556 (13)	−0.0003 (11)	0.0078 (11)	0.0016 (10)
C8	0.0475 (11)	0.0334 (10)	0.0504 (11)	0.0002 (9)	0.0148 (9)	0.0041 (9)
C9	0.0587 (13)	0.0550 (14)	0.0591 (13)	0.0085 (11)	0.0190 (11)	−0.0022 (10)
C10	0.0499 (13)	0.0563 (14)	0.0808 (17)	0.0067 (11)	0.0077 (12)	0.0102 (12)
C11	0.0587 (13)	0.0477 (13)	0.0606 (13)	−0.0144 (11)	0.0025 (10)	0.0115 (11)
C12	0.0684 (14)	0.0596 (14)	0.0551 (13)	−0.0068 (12)	0.0126 (11)	−0.0109 (11)
C13	0.0549 (12)	0.0498 (13)	0.0591 (13)	0.0062 (10)	0.0140 (10)	−0.0053 (10)
C14	0.0839 (17)	0.092 (2)	0.0770 (17)	−0.0257 (15)	−0.0137 (14)	0.0242 (14)
C15	0.0822 (19)	0.0621 (17)	0.127 (2)	−0.0281 (14)	−0.0092 (17)	0.0158 (16)
C16	0.0726 (16)	0.0589 (16)	0.0998 (19)	−0.0182 (13)	−0.0212 (14)	0.0224 (13)
C17	0.0542 (12)	0.0437 (11)	0.0364 (10)	−0.0062 (10)	0.0049 (9)	−0.0006 (8)
C18	0.0802 (16)	0.0666 (16)	0.0721 (15)	−0.0210 (13)	−0.0252 (13)	0.0218 (12)
C19	0.110 (2)	0.0661 (17)	0.0666 (16)	−0.0104 (16)	−0.0159 (15)	0.0225 (13)
N1	0.0848 (12)	0.0381 (10)	0.0466 (9)	−0.0041 (9)	0.0182 (9)	0.0006 (7)
N2	0.0893 (15)	0.0513 (12)	0.0658 (12)	−0.0105 (11)	0.0208 (11)	0.0070 (10)
O1	0.1032 (13)	0.0362 (9)	0.1041 (13)	0.0068 (9)	0.0379 (10)	0.0035 (8)
O2	0.1009 (13)	0.0472 (9)	0.0918 (12)	0.0005 (9)	0.0475 (10)	0.0116 (9)
O3	0.0551 (8)	0.0692 (10)	0.0733 (10)	0.0123 (8)	0.0112 (7)	0.0181 (8)
O4	0.0911 (11)	0.0506 (9)	0.0640 (9)	−0.0236 (8)	0.0055 (8)	0.0020 (7)
S1	0.0603 (3)	0.0455 (3)	0.0507 (3)	−0.0042 (3)	0.0078 (2)	0.0067 (2)

Geometric parameters (Å, º) top

C1—C2	1.382 (3)	C12—H12	0.9300
C1—C6	1.389 (2)	C13—H13	0.9300
C1—C7	1.482 (3)	C14—H14A	0.9600
C2—C3	1.379 (3)	C14—H14B	0.9600
C2—H2	0.9300	C14—H14C	0.9600
C3—C4	1.387 (3)	C14—H14D	0.9600
C3—H3	0.9300	C14—H14E	0.9600
C4—C5	1.383 (3)	C14—H14F	0.9600
C4—N1	1.419 (2)	C15—N2	1.309 (3)
C5—C6	1.377 (3)	C15—C16	1.376 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.360 (3)
C7—O1	1.207 (2)	C16—H16	0.9300
C7—O2	1.310 (2)	C17—C18	1.367 (3)
C8—C9	1.378 (3)	C17—C17ⁱ	1.485 (3)
C8—C13	1.379 (3)	C18—C19	1.379 (3)
C8—S1	1.7563 (19)	C18—H18	0.9300
C9—C10	1.370 (3)	C19—N2	1.300 (3)
C9—H9	0.9300	C19—H19	0.9300
C10—C11	1.391 (3)	N1—S1	1.6253 (16)
C10—H10	0.9300	N1—H1	0.8600
C11—C12	1.375 (3)	O2—H2A	0.8200
C11—C14	1.503 (3)	O3—S1	1.4254 (14)
C12—C13	1.375 (3)	O4—S1	1.4300 (14)

C2—C1—C6	118.52 (18)	H14A—C14—H14C	109.5
C2—C1—C7	119.73 (18)	H14B—C14—H14C	109.5
C6—C1—C7	121.73 (18)	C11—C14—H14D	109.5
C3—C2—C1	121.22 (19)	H14A—C14—H14D	141.1
C3—C2—H2	119.4	H14B—C14—H14D	56.3
C1—C2—H2	119.4	H14C—C14—H14D	56.3
C2—C3—C4	119.8 (2)	C11—C14—H14E	109.5
C2—C3—H3	120.1	H14A—C14—H14E	56.3
C4—C3—H3	120.1	H14B—C14—H14E	141.1
C5—C4—C3	119.45 (18)	H14C—C14—H14E	56.3
C5—C4—N1	117.54 (17)	H14D—C14—H14E	109.5
C3—C4—N1	122.87 (19)	C11—C14—H14F	109.5
C6—C5—C4	120.33 (18)	H14A—C14—H14F	56.3
C6—C5—H5	119.8	H14B—C14—H14F	56.3
C4—C5—H5	119.8	H14C—C14—H14F	141.1
C5—C6—C1	120.66 (19)	H14D—C14—H14F	109.5
C5—C6—H6	119.7	H14E—C14—H14F	109.5
C1—C6—H6	119.7	N2—C15—C16	124.4 (2)
O1—C7—O2	122.1 (2)	N2—C15—H15	117.8
O1—C7—C1	124.1 (2)	C16—C15—H15	117.8
O2—C7—C1	113.71 (18)	C17—C16—C15	120.1 (2)
C9—C8—C13	119.75 (19)	C17—C16—H16	120.0
C9—C8—S1	119.75 (15)	C15—C16—H16	120.0
C13—C8—S1	120.35 (15)	C16—C17—C18	115.33 (19)
C10—C9—C8	119.48 (19)	C16—C17—C17ⁱ	122.4 (2)
C10—C9—H9	120.3	C18—C17—C17ⁱ	122.3 (2)
C8—C9—H9	120.3	C17—C18—C19	120.6 (2)
C9—C10—C11	121.8 (2)	C17—C18—H18	119.7
C9—C10—H10	119.1	C19—C18—H18	119.7
C11—C10—H10	119.1	N2—C19—C18	123.8 (2)
C12—C11—C10	117.5 (2)	N2—C19—H19	118.1
C12—C11—C14	121.9 (2)	C18—C19—H19	118.1
C10—C11—C14	120.6 (2)	C4—N1—S1	128.58 (14)
C11—C12—C13	121.5 (2)	C4—N1—H1	115.7
C11—C12—H12	119.3	S1—N1—H1	115.7
C13—C12—H12	119.3	C19—N2—C15	115.7 (2)
C12—C13—C8	119.96 (19)	C7—O2—H2A	109.5
C12—C13—H13	120.0	O3—S1—O4	119.64 (10)
C8—C13—H13	120.0	O3—S1—N1	109.31 (9)
C11—C14—H14A	109.5	O4—S1—N1	104.32 (9)
C11—C14—H14B	109.5	O3—S1—C8	108.50 (9)
H14A—C14—H14B	109.5	O4—S1—C8	107.93 (9)
C11—C14—H14C	109.5	N1—S1—C8	106.38 (9)

C6—C1—C2—C3	−2.1 (3)	C9—C8—C13—C12	−0.5 (3)
C7—C1—C2—C3	176.19 (18)	S1—C8—C13—C12	175.18 (15)
C1—C2—C3—C4	0.9 (3)	N2—C15—C16—C17	−0.2 (5)
C2—C3—C4—C5	1.3 (3)	C15—C16—C17—C18	−0.2 (4)
C2—C3—C4—N1	−174.24 (18)	C15—C16—C17—C17ⁱ	−179.4 (3)
C3—C4—C5—C6	−2.3 (3)	C16—C17—C18—C19	0.7 (4)
N1—C4—C5—C6	173.49 (16)	C17ⁱ—C17—C18—C19	179.9 (2)
C4—C5—C6—C1	1.1 (3)	C17—C18—C19—N2	−0.9 (4)
C2—C1—C6—C5	1.1 (3)	C5—C4—N1—S1	153.34 (15)
C7—C1—C6—C5	−177.15 (18)	C3—C4—N1—S1	−31.0 (3)
C2—C1—C7—O1	7.0 (3)	C18—C19—N2—C15	0.5 (4)
C6—C1—C7—O1	−174.8 (2)	C16—C15—N2—C19	0.1 (4)
C2—C1—C7—O2	−169.59 (19)	C4—N1—S1—O3	42.72 (19)
C6—C1—C7—O2	8.6 (3)	C4—N1—S1—O4	171.78 (16)
C13—C8—C9—C10	0.0 (3)	C4—N1—S1—C8	−74.25 (18)
S1—C8—C9—C10	−175.72 (15)	C9—C8—S1—O3	−169.22 (15)
C8—C9—C10—C11	0.8 (3)	C13—C8—S1—O3	15.07 (18)
C9—C10—C11—C12	−1.0 (3)	C9—C8—S1—O4	59.76 (17)
C9—C10—C11—C14	179.9 (2)	C13—C8—S1—O4	−115.95 (17)
C10—C11—C12—C13	0.5 (3)	C9—C8—S1—N1	−51.71 (17)
C14—C11—C12—C13	179.54 (19)	C13—C8—S1—N1	132.58 (16)
C11—C12—C13—C8	0.3 (3)

Symmetry code: (i) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱⁱ	0.86	2.03	2.861 (2)	162
O2—H2A···N2ⁱⁱⁱ	0.82	1.87	2.691 (2)	175
C2—H2···O4ⁱⁱⁱ	0.93	2.51	3.413 (2)	163

Symmetry codes: (ii) x, y−1, z; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₄S·0.5C₁₀H₈N₂
M_r	369.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	5.8732 (7), 8.124 (1), 36.806 (5)
β (°)	94.137 (2)
V (Å³)	1751.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.39 × 0.24 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.922, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	7704, 3234, 2255
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.107, 0.99
No. of reflections	3234
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.24

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.03	2.861 (2)	162
O2—H2A···N2ⁱⁱ	0.82	1.87	2.691 (2)	175
C2—H2···O4ⁱⁱ	0.93	2.51	3.413 (2)	163

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

Acknowledgements

This work was supported by the Master Construction Project of Quanzhou Normal University, China.

References

Antolini, L., Menabue, L., Saladini, M., Pellacani, G. C., Battaglia, L. P., Sola, M. & Bonamartini Corradi, A. (1984). J. Chem. Soc. Dalton Trans. pp. 2319–2323. CSD CrossRef Web of Science Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Menabue, L. & Saladini, M. (1988). Acta Cryst. C44, 2087–2089. CSD CrossRef Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar