2,4,6-Tris(1-oxo-2-pyridylsulfanylmeth­yl)mesitylene methanol solvate

Ravindran Durai Nayagam, B.; Jebas, S.R.; Ravi Samuelraj, C.; Schollmeyer, D.

doi:10.1107/S1600536808013081

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o1036-o1037

doi:10.1107/S1600536808013081

Open

access

2,4,6-Tris(1-oxo-2-pyridylsulfanylmethyl)mesitylene methanol solvate

B. Ravindran Durai Nayagam,^a ^* Samuel Robinson Jebas,^b C. Ravi Samuelraj ^a and Dieter Schollmeyer ^c

^aDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamil Nadu, India, ^bDepartment of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India, and ^cInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: b_ravidurai@yahoo.com

(Received 1 May 2008; accepted 3 May 2008; online 10 May 2008)

In the title compound, C₂₇H₂₇N₃O₃S₃·CH₄O, the dihedral angles formed by the mesitylene ring with the three oxopyridyl rings are 89.6 (1), 75.5 (1) and 80.69 (1)°, indicating that all three are nearly perpendicular to the mesitylene ring. Intramolecular C—H⋯S hydrogen bonds generate S(6) ring motifs. The crystal structure is stabilized by intramolecular C—H⋯S and intermolecular C—H⋯O hydrogen bonds and weak C—H⋯π interactions.

Related literature

For related literature on the biological activity of N-oxides see: Lobana et al., (1989 ); Symons & West (1985 ); Katsuyuki et al. (1991 ); Bovin et al. (1992 ); Leonard et al.(1955 ). For related literature on N-oxides, see: Jebas et al. (2005 ); Ravindran et al. (2008 ). For bond-length data, see: Allen et al. (1987 ); Jebas et al. (2005); Ravindran et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₇H₂₇N₃O₃S₃·CH₄O
M_r = 569.74
Monoclinic, P 2₁ /c
a = 11.9644 (17) Å
b = 14.9129 (8) Å
c = 15.467 (2) Å
β = 91.733 (7)°
V = 2758.4 (6) Å³
Z = 4
Cu Kα radiation
μ = 2.78 mm⁻¹
T = 298 (2) K
0.52 × 0.42 × 0.06 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.296, T_max = 0.842
5226 measured reflections
5226 independent reflections
4156 reflections with I > 2σ(I)
3 standard reflections frequency: 60 min intensity decay: 3%

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.150
S = 1.08
5226 reflections
347 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1L—H1L⋯O27	0.82	2.41	2.804 (7)	110
C16—H16A⋯O36ⁱ	0.96	2.47	3.348 (4)	152
C16—H16B⋯S20	0.96	2.68	3.420 (3)	135
C18—H18B⋯S29	0.96	2.79	3.515 (3)	133
C25—H25⋯O7ⁱⁱ	0.93	2.44	3.147 (5)	133
C28—H28A⋯O7ⁱ	0.97	2.48	3.397 (3)	157
C31—H31⋯O27ⁱⁱⁱ	0.93	2.35	3.107 (4)	139
C2—H2⋯Cg1^iv	0.93	2.91	3.774 (3)	154
C4—H4⋯Cg1^v	0.93	2.67	3.377 (3)	134
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) -x+1, -y+1, -z; (v) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ . Cg1 is the centroid of the C10–C15 ring.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; 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: 10.1107/S1600536808013081/at2565sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013081/at2565Isup2.hkl

checkCIF report

Comment top

N-Oxides and their derivatives show a broad spectrum of biological activity, such as antifungal, antibacterial, antimicrobial and antibacterial activities (Lobana & Bhatia, 1989; Symons et al.,1985). These compounds are also found to be involved in DNA strand scission under physiological conditions (Katsuyuki et al.,1991; Bovin et al. 1992). Pyridine N-oxides bearing a sulfur group in position 2 display significant antimicrobial activity (Leonard et al.,1955). In view of the importance of N-oxides, we have previously reported the crystal structures of N-oxide derivatives (Jebas et al., 2005; Ravindran et al., 2008). As an extension of our work on these derivatives, we report here the crystal structure of the title compound (Fig. 1).

The bond lengths and angles agree well with the N-oxide derivatives reported earlier (Jebas et al., 2005; Ravindran et al., 2008). The N–O bond length is in good agreement with the mean value of 1.304 (15) Å reported in the literature for pyridine N–oxides (Allen et al.,1987).

The meistylene ring is planar with the maximum deviation from planarity being -0.036 (1) Å. The dihedral angle formed by the meistylene ring with the oxopyridinium rings (C1–C5/N6) 89.6 (1) °; (C21–C25/N26) 75.5 (1) ° and (C30–C34/N35) 80.69 (1) ° respectively, indicating that all the three oxopyridinium rings are perpendicular to the meistylene ring.

Intramolecular C—H···S hydrogen bonds generate S(6)S(6) ring motifs. The crystal structure is stabilized by intramolecular C—H···S and intermolecular C—H··· O hydrogen bonds and weak C—H···π interactions (Table 1, where Cg1 is the centroid of the ring C10-C15).

Related literature top

For related literature on the biological activity of N-oxides see: Lobana et al., (1989); Symons & West (1985); Katsuyuki et al. (1991); Bovin et al. (1992); Leonard et al.(1955). For related literature on N-oxides see: Jebas et al. (2005); Ravindran et al. (2008). For bond-length data, see: Allen et al. (1987); Jebas et al. (2005); Ravindran et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995). Cg1 is the centroid of the ring C10–C15.

Experimental top

A mixture of tris(bromomethyl)mesitylene (0.399 g, 1 mmol) and 1-hydroxypyridine-2-thione sodium salt (0.448 g, 3 mmol) in water (30 ml) and methanol (30 ml) was heated at 333 K with stirring for 30 min. The compound formed was filtered off, and dried (0.494 g, 92%). The compound was recrystallized from chloroform-methanol (1:2 v/v).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CAD-4 Software (Enraf–Nonius, 1989); 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 molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering scheme.

2,4,6-Tris(1-oxo-2-pyridylsulfanylmethyl)mesitylene methanol solvate top

Crystal data top

C₂₇H₂₇N₃O₃S₃·CH₄O	F(000) = 1200
M_r = 569.74	D_x = 1.372 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.9644 (17) Å	θ = 61–69°
b = 14.9129 (8) Å	µ = 2.78 mm⁻¹
c = 15.467 (2) Å	T = 298 K
β = 91.733 (7)°	Block, colourless
V = 2758.4 (6) Å³	0.52 × 0.42 × 0.06 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	4156 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0
Graphite monochromator	θ_max = 69.9°, θ_min = 3.7°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = −18→0
T_min = 0.296, T_max = 0.842	l = −18→18
5226 measured reflections	3 standard reflections every 60 min
5226 independent reflections	intensity decay: 3%

Refinement top

Refinement on F²	12 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0834P)² + 0.7123P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.150	(Δ/σ)_max = 0.001
S = 1.09	Δρ_max = 0.49 e Å⁻³
5226 reflections	Δρ_min = −0.32 e Å⁻³
347 parameters

Crystal data top

C₂₇H₂₇N₃O₃S₃·CH₄O	V = 2758.4 (6) Å³
M_r = 569.74	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.9644 (17) Å	µ = 2.78 mm⁻¹
b = 14.9129 (8) Å	T = 298 K
c = 15.467 (2) Å	0.52 × 0.42 × 0.06 mm
β = 91.733 (7)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	4156 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0
T_min = 0.296, T_max = 0.842	3 standard reflections every 60 min
5226 measured reflections	intensity decay: 3%
5226 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	12 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.09	Δρ_max = 0.49 e Å⁻³
5226 reflections	Δρ_min = −0.32 e Å⁻³
347 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.3585 (2)	0.25409 (17)	−0.03619 (16)	0.0411 (6)
C2	0.4031 (2)	0.2831 (2)	−0.11233 (17)	0.0509 (7)
H2	0.4415	0.3372	−0.114	0.061*
C3	0.3906 (3)	0.2318 (2)	−0.18594 (19)	0.0595 (8)
H3	0.4189	0.2516	−0.2379	0.071*
C4	0.3357 (3)	0.1508 (2)	−0.1818 (2)	0.0627 (8)
H4	0.3283	0.1149	−0.2307	0.075*
C5	0.2921 (3)	0.1234 (2)	−0.1054 (2)	0.0593 (8)
H5	0.2552	0.0686	−0.1028	0.071*
N6	0.30179 (19)	0.17480 (15)	−0.03383 (15)	0.0475 (5)
O7	0.2579 (2)	0.15045 (15)	0.03880 (14)	0.0660 (6)
S8	0.36161 (6)	0.30782 (4)	0.06449 (4)	0.04599 (19)
C9	0.4460 (2)	0.40587 (17)	0.04115 (15)	0.0442 (6)
H9A	0.5203	0.3879	0.0245	0.053*
H9B	0.4117	0.4404	−0.0057	0.053*
C10	0.4525 (2)	0.46111 (16)	0.12348 (15)	0.0380 (5)
C11	0.3677 (2)	0.52357 (17)	0.13909 (16)	0.0407 (5)
C12	0.3725 (2)	0.57310 (16)	0.21599 (16)	0.0401 (5)
C13	0.4580 (2)	0.55854 (16)	0.27863 (16)	0.0401 (5)
C14	0.5453 (2)	0.49992 (16)	0.25966 (15)	0.0384 (5)
C15	0.5413 (2)	0.44950 (16)	0.18286 (15)	0.0384 (5)
C16	0.2719 (3)	0.5372 (2)	0.07464 (19)	0.0551 (7)
H16A	0.2881	0.5871	0.0378	0.083*
H16B	0.2047	0.5491	0.1049	0.083*
H16C	0.2621	0.4841	0.0401	0.083*
C17	0.4548 (3)	0.6036 (2)	0.36637 (19)	0.0588 (8)
H17A	0.4966	0.6585	0.3652	0.088*
H17B	0.487	0.5645	0.4096	0.088*
H17C	0.3786	0.6164	0.3799	0.088*
C18	0.6333 (3)	0.3827 (2)	0.16668 (19)	0.0535 (7)
H18A	0.6067	0.3384	0.126	0.08*
H18B	0.6552	0.354	0.2201	0.08*
H18C	0.6964	0.4133	0.1437	0.08*
C19	0.2853 (2)	0.64413 (18)	0.2303 (2)	0.0489 (6)
H19A	0.2688	0.6758	0.1766	0.059*
H19B	0.313	0.6872	0.2728	0.059*
S20	0.15895 (7)	0.59076 (5)	0.26844 (6)	0.0598 (2)
C21	0.0714 (2)	0.6832 (2)	0.2755 (2)	0.0534 (7)
C22	0.0959 (3)	0.7726 (2)	0.2634 (2)	0.0627 (8)
H22	0.167	0.7891	0.2465	0.075*
C23	0.0164 (3)	0.8378 (3)	0.2760 (3)	0.0754 (10)
H23	0.0333	0.898	0.2674	0.09*
C24	−0.0876 (3)	0.8128 (3)	0.3012 (3)	0.0837 (12)
H24	−0.1412	0.8561	0.3121	0.1*
C25	−0.1127 (3)	0.7240 (3)	0.3104 (3)	0.0831 (12)
H25	−0.1841	0.7072	0.3263	0.1*
N26	−0.0351 (2)	0.6605 (2)	0.29666 (19)	0.0687 (8)
O27	−0.0591 (2)	0.57455 (19)	0.3027 (2)	0.0984 (10)
C28	0.6442 (2)	0.49055 (18)	0.32203 (17)	0.0450 (6)
H28A	0.6531	0.5448	0.3561	0.054*
H28B	0.712	0.4813	0.2903	0.054*
S29	0.62016 (6)	0.39480 (5)	0.39312 (5)	0.0517 (2)
C30	0.7555 (2)	0.37491 (19)	0.43343 (17)	0.0475 (6)
C31	0.8492 (3)	0.4281 (2)	0.4247 (2)	0.0604 (8)
H31	0.8431	0.4844	0.3993	0.073*
C32	0.9529 (3)	0.3962 (3)	0.4545 (3)	0.0771 (10)
H32	1.0171	0.4301	0.4475	0.093*
C33	0.9589 (4)	0.3142 (3)	0.4943 (3)	0.0871 (13)
H33	1.0278	0.2922	0.5142	0.104*
C34	0.8648 (4)	0.2647 (3)	0.5050 (2)	0.0772 (11)
H34	0.8701	0.2094	0.5327	0.093*
N35	0.7633 (2)	0.29458 (17)	0.47588 (16)	0.0572 (6)
O36	0.6727 (2)	0.24782 (16)	0.48565 (16)	0.0756 (7)
O1L	−0.1572 (5)	0.5507 (4)	0.1374 (4)	0.205 (2)
H1L	−0.12	0.5136	0.1649	0.308*
C2L	−0.0867 (7)	0.5996 (6)	0.0829 (5)	0.189 (3)
H2LA	−0.0521	0.6478	0.115	0.284*
H2LB	−0.1301	0.6237	0.0351	0.284*
H2LC	−0.03	0.5606	0.0615	0.284*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0480 (14)	0.0322 (12)	0.0432 (13)	0.0010 (10)	0.0013 (11)	−0.0040 (10)
C2	0.0599 (16)	0.0485 (16)	0.0447 (14)	−0.0036 (13)	0.0087 (12)	−0.0060 (12)
C3	0.0659 (19)	0.066 (2)	0.0471 (15)	0.0032 (16)	0.0085 (14)	−0.0108 (14)
C4	0.0639 (18)	0.065 (2)	0.0594 (18)	0.0085 (16)	−0.0044 (15)	−0.0287 (16)
C5	0.0639 (18)	0.0428 (16)	0.071 (2)	−0.0009 (14)	−0.0044 (15)	−0.0194 (14)
N6	0.0517 (12)	0.0371 (12)	0.0536 (13)	−0.0005 (10)	0.0007 (10)	−0.0030 (10)
O7	0.0869 (16)	0.0497 (12)	0.0620 (13)	−0.0199 (11)	0.0136 (12)	0.0040 (10)
S8	0.0649 (4)	0.0383 (3)	0.0351 (3)	−0.0115 (3)	0.0081 (3)	−0.0010 (2)
C9	0.0598 (16)	0.0381 (14)	0.0352 (12)	−0.0108 (12)	0.0078 (11)	−0.0017 (10)
C10	0.0494 (14)	0.0304 (12)	0.0346 (12)	−0.0079 (10)	0.0060 (10)	0.0004 (9)
C11	0.0465 (13)	0.0332 (12)	0.0425 (13)	−0.0049 (10)	0.0034 (11)	0.0048 (10)
C12	0.0450 (13)	0.0290 (12)	0.0467 (13)	−0.0001 (10)	0.0082 (11)	0.0028 (10)
C13	0.0497 (14)	0.0294 (12)	0.0416 (13)	0.0001 (10)	0.0079 (11)	−0.0017 (10)
C14	0.0464 (13)	0.0305 (12)	0.0384 (12)	−0.0026 (10)	0.0037 (10)	0.0024 (10)
C15	0.0477 (13)	0.0293 (12)	0.0387 (12)	−0.0008 (10)	0.0094 (10)	0.0007 (9)
C16	0.0574 (17)	0.0541 (17)	0.0534 (16)	0.0011 (14)	−0.0053 (13)	0.0049 (13)
C17	0.074 (2)	0.0518 (17)	0.0513 (16)	0.0057 (15)	0.0062 (14)	−0.0164 (13)
C18	0.0585 (17)	0.0464 (16)	0.0557 (16)	0.0127 (13)	0.0063 (13)	−0.0059 (13)
C19	0.0485 (14)	0.0331 (13)	0.0655 (17)	0.0037 (11)	0.0095 (13)	0.0016 (12)
S20	0.0567 (4)	0.0417 (4)	0.0823 (5)	0.0054 (3)	0.0209 (4)	0.0093 (3)
C21	0.0492 (15)	0.0523 (17)	0.0592 (17)	0.0065 (13)	0.0094 (13)	0.0061 (13)
C22	0.0565 (17)	0.0502 (17)	0.082 (2)	0.0055 (14)	0.0066 (16)	0.0005 (16)
C23	0.073 (2)	0.054 (2)	0.100 (3)	0.0166 (18)	0.006 (2)	0.0046 (19)
C24	0.074 (2)	0.078 (3)	0.099 (3)	0.032 (2)	0.014 (2)	0.010 (2)
C25	0.0563 (19)	0.096 (3)	0.099 (3)	0.020 (2)	0.0250 (19)	0.020 (2)
N26	0.0583 (15)	0.0674 (18)	0.0815 (19)	0.0050 (14)	0.0231 (14)	0.0188 (15)
O27	0.0813 (18)	0.0709 (17)	0.146 (3)	−0.0036 (14)	0.0488 (18)	0.0273 (17)
C28	0.0495 (14)	0.0383 (14)	0.0471 (14)	−0.0038 (11)	−0.0007 (12)	0.0030 (11)
S29	0.0522 (4)	0.0503 (4)	0.0524 (4)	−0.0049 (3)	−0.0013 (3)	0.0111 (3)
C30	0.0598 (16)	0.0425 (14)	0.0399 (13)	0.0037 (12)	−0.0041 (12)	−0.0029 (11)
C31	0.0605 (18)	0.0562 (18)	0.0639 (18)	−0.0008 (15)	−0.0104 (15)	−0.0032 (15)
C32	0.058 (2)	0.085 (3)	0.087 (3)	0.0017 (18)	−0.0141 (18)	−0.015 (2)
C33	0.080 (3)	0.092 (3)	0.087 (3)	0.030 (2)	−0.032 (2)	−0.016 (2)
C34	0.101 (3)	0.066 (2)	0.064 (2)	0.025 (2)	−0.022 (2)	0.0010 (17)
N35	0.0801 (18)	0.0444 (14)	0.0467 (13)	0.0080 (13)	−0.0035 (12)	0.0002 (11)
O36	0.0988 (18)	0.0528 (14)	0.0755 (15)	−0.0065 (13)	0.0083 (14)	0.0178 (12)
O1L	0.213 (4)	0.187 (4)	0.214 (4)	−0.065 (4)	−0.012 (3)	−0.012 (3)
C2L	0.178 (5)	0.210 (5)	0.179 (5)	−0.041 (4)	−0.017 (4)	0.006 (4)

Geometric parameters (Å, º) top

C1—N6	1.364 (3)	C19—S20	1.822 (3)
C1—C2	1.377 (4)	C19—H19A	0.97
C1—S8	1.751 (2)	C19—H19B	0.97
C2—C3	1.376 (4)	S20—C21	1.737 (3)
C2—H2	0.93	C21—N26	1.368 (4)
C3—C4	1.377 (5)	C21—C22	1.378 (4)
C3—H3	0.93	C22—C23	1.379 (4)
C4—C5	1.368 (5)	C22—H22	0.93
C4—H4	0.93	C23—C24	1.368 (5)
C5—N6	1.349 (4)	C23—H23	0.93
C5—H5	0.93	C24—C25	1.366 (6)
N6—O7	1.306 (3)	C24—H24	0.93
S8—C9	1.820 (3)	C25—N26	1.348 (5)
C9—C10	1.517 (3)	C25—H25	0.93
C9—H9A	0.97	N26—O27	1.318 (4)
C9—H9B	0.97	C28—S29	1.830 (3)
C10—C15	1.394 (4)	C28—H28A	0.97
C10—C11	1.404 (4)	C28—H28B	0.97
C11—C12	1.400 (4)	S29—C30	1.742 (3)
C11—C16	1.510 (4)	C30—N35	1.368 (4)
C12—C13	1.404 (4)	C30—C31	1.384 (4)
C12—C19	1.508 (3)	C31—C32	1.394 (5)
C13—C14	1.400 (3)	C31—H31	0.93
C13—C17	1.516 (4)	C32—C33	1.370 (6)
C14—C15	1.406 (3)	C32—H32	0.93
C14—C28	1.510 (3)	C33—C34	1.361 (6)
C15—C18	1.511 (4)	C33—H33	0.93
C16—H16A	0.96	C34—N35	1.358 (4)
C16—H16B	0.96	C34—H34	0.93
C16—H16C	0.96	N35—O36	1.302 (4)
C17—H17A	0.96	O1L—C2L	1.414 (9)
C17—H17B	0.96	O1L—H1L	0.82
C17—H17C	0.96	C2L—H2LA	0.96
C18—H18A	0.96	C2L—H2LB	0.96
C18—H18B	0.96	C2L—H2LC	0.96
C18—H18C	0.96

N6—C1—C2	120.1 (2)	H18A—C18—H18C	109.5
N6—C1—S8	111.72 (18)	H18B—C18—H18C	109.5
C2—C1—S8	128.2 (2)	C12—C19—S20	108.98 (18)
C3—C2—C1	119.8 (3)	C12—C19—H19A	109.9
C3—C2—H2	120.1	S20—C19—H19A	109.9
C1—C2—H2	120.1	C12—C19—H19B	109.9
C2—C3—C4	119.3 (3)	S20—C19—H19B	109.9
C2—C3—H3	120.4	H19A—C19—H19B	108.3
C4—C3—H3	120.4	C21—S20—C19	100.44 (13)
C5—C4—C3	119.8 (3)	N26—C21—C22	118.4 (3)
C5—C4—H4	120.1	N26—C21—S20	112.7 (2)
C3—C4—H4	120.1	C22—C21—S20	128.9 (2)
N6—C5—C4	120.9 (3)	C21—C22—C23	120.8 (3)
N6—C5—H5	119.6	C21—C22—H22	119.6
C4—C5—H5	119.6	C23—C22—H22	119.6
O7—N6—C5	121.4 (2)	C24—C23—C22	119.0 (4)
O7—N6—C1	118.5 (2)	C24—C23—H23	120.5
C5—N6—C1	120.1 (3)	C22—C23—H23	120.5
C1—S8—C9	100.86 (12)	C25—C24—C23	119.9 (3)
C10—C9—S8	106.53 (16)	C25—C24—H24	120
C10—C9—H9A	110.4	C23—C24—H24	120
S8—C9—H9A	110.4	N26—C25—C24	120.7 (3)
C10—C9—H9B	110.4	N26—C25—H25	119.7
S8—C9—H9B	110.4	C24—C25—H25	119.7
H9A—C9—H9B	108.6	O27—N26—C25	121.3 (3)
C15—C10—C11	120.6 (2)	O27—N26—C21	117.7 (3)
C15—C10—C9	120.3 (2)	C25—N26—C21	121.0 (3)
C11—C10—C9	119.1 (2)	C14—C28—S29	108.76 (17)
C12—C11—C10	119.0 (2)	C14—C28—H28A	109.9
C12—C11—C16	120.1 (2)	S29—C28—H28A	109.9
C10—C11—C16	120.9 (2)	C14—C28—H28B	109.9
C11—C12—C13	121.0 (2)	S29—C28—H28B	109.9
C11—C12—C19	119.0 (2)	H28A—C28—H28B	108.3
C13—C12—C19	120.0 (2)	C30—S29—C28	100.76 (13)
C14—C13—C12	119.0 (2)	N35—C30—C31	120.3 (3)
C14—C13—C17	120.3 (2)	N35—C30—S29	111.7 (2)
C12—C13—C17	120.7 (2)	C31—C30—S29	127.9 (2)
C13—C14—C15	120.3 (2)	C30—C31—C32	119.2 (3)
C13—C14—C28	119.9 (2)	C30—C31—H31	120.4
C15—C14—C28	119.8 (2)	C32—C31—H31	120.4
C10—C15—C14	119.8 (2)	C33—C32—C31	119.2 (4)
C10—C15—C18	121.1 (2)	C33—C32—H32	120.4
C14—C15—C18	119.1 (2)	C31—C32—H32	120.4
C11—C16—H16A	109.5	C34—C33—C32	120.4 (4)
C11—C16—H16B	109.5	C34—C33—H33	119.8
H16A—C16—H16B	109.5	C32—C33—H33	119.8
C11—C16—H16C	109.5	N35—C34—C33	121.1 (4)
H16A—C16—H16C	109.5	N35—C34—H34	119.4
H16B—C16—H16C	109.5	C33—C34—H34	119.4
C13—C17—H17A	109.5	O36—N35—C34	121.7 (3)
C13—C17—H17B	109.5	O36—N35—C30	118.7 (3)
H17A—C17—H17B	109.5	C34—N35—C30	119.6 (3)
C13—C17—H17C	109.5	C2L—O1L—H1L	109.5
H17A—C17—H17C	109.5	O1L—C2L—H2LA	109.5
H17B—C17—H17C	109.5	O1L—C2L—H2LB	109.5
C15—C18—H18A	109.5	H2LA—C2L—H2LB	109.5
C15—C18—H18B	109.5	O1L—C2L—H2LC	109.5
H18A—C18—H18B	109.5	H2LA—C2L—H2LC	109.5
C15—C18—H18C	109.5	H2LB—C2L—H2LC	109.5

N6—C1—C2—C3	−0.2 (4)	C13—C14—C15—C10	3.0 (3)
S8—C1—C2—C3	−178.9 (2)	C28—C14—C15—C10	−177.1 (2)
C1—C2—C3—C4	−1.6 (5)	C13—C14—C15—C18	−176.4 (2)
C2—C3—C4—C5	1.6 (5)	C28—C14—C15—C18	3.5 (3)
C3—C4—C5—N6	0.2 (5)	C11—C12—C19—S20	81.2 (3)
C4—C5—N6—O7	178.1 (3)	C13—C12—C19—S20	−99.9 (2)
C4—C5—N6—C1	−1.9 (4)	C12—C19—S20—C21	−177.6 (2)
C2—C1—N6—O7	−178.1 (3)	C19—S20—C21—N26	174.9 (2)
S8—C1—N6—O7	0.8 (3)	C19—S20—C21—C22	−5.5 (4)
C2—C1—N6—C5	1.9 (4)	N26—C21—C22—C23	2.8 (5)
S8—C1—N6—C5	−179.1 (2)	S20—C21—C22—C23	−176.7 (3)
N6—C1—S8—C9	177.65 (19)	C21—C22—C23—C24	0.3 (6)
C2—C1—S8—C9	−3.5 (3)	C22—C23—C24—C25	−2.5 (7)
C1—S8—C9—C10	178.14 (19)	C23—C24—C25—N26	1.5 (7)
S8—C9—C10—C15	92.9 (2)	C24—C25—N26—O27	−177.9 (4)
S8—C9—C10—C11	−86.7 (2)	C24—C25—N26—C21	1.8 (6)
C15—C10—C11—C12	−1.1 (3)	C22—C21—N26—O27	175.8 (3)
C9—C10—C11—C12	178.6 (2)	S20—C21—N26—O27	−4.5 (4)
C15—C10—C11—C16	179.3 (2)	C22—C21—N26—C25	−3.9 (5)
C9—C10—C11—C16	−1.0 (3)	S20—C21—N26—C25	175.7 (3)
C10—C11—C12—C13	−2.6 (4)	C13—C14—C28—S29	94.8 (2)
C16—C11—C12—C13	177.0 (2)	C15—C14—C28—S29	−85.0 (2)
C10—C11—C12—C19	176.3 (2)	C14—C28—S29—C30	162.19 (18)
C16—C11—C12—C19	−4.1 (4)	C28—S29—C30—N35	−168.0 (2)
C11—C12—C13—C14	6.3 (4)	C28—S29—C30—C31	10.1 (3)
C19—C12—C13—C14	−172.5 (2)	N35—C30—C31—C32	4.3 (5)
C11—C12—C13—C17	−172.2 (2)	S29—C30—C31—C32	−173.7 (3)
C19—C12—C13—C17	9.0 (4)	C30—C31—C32—C33	−2.1 (5)
C12—C13—C14—C15	−6.5 (3)	C31—C32—C33—C34	−0.3 (6)
C17—C13—C14—C15	172.0 (2)	C32—C33—C34—N35	0.7 (6)
C12—C13—C14—C28	173.6 (2)	C33—C34—N35—O36	180.0 (3)
C17—C13—C14—C28	−7.9 (4)	C33—C34—N35—C30	1.4 (5)
C11—C10—C15—C14	0.8 (3)	C31—C30—N35—O36	177.5 (3)
C9—C10—C15—C14	−178.9 (2)	S29—C30—N35—O36	−4.2 (3)
C11—C10—C15—C18	−179.8 (2)	C31—C30—N35—C34	−3.9 (4)
C9—C10—C15—C18	0.5 (3)	S29—C30—N35—C34	174.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1L—H1L···O27	0.82	2.41	2.804 (7)	110
C16—H16A···O36ⁱ	0.96	2.47	3.348 (4)	152
C16—H16B···S20	0.96	2.68	3.420 (3)	135
C18—H18B···S29	0.96	2.79	3.515 (3)	133
C25—H25···O7ⁱⁱ	0.93	2.44	3.147 (5)	133
C28—H28A···O7ⁱ	0.97	2.48	3.397 (3)	157
C31—H31···O27ⁱⁱⁱ	0.93	2.35	3.107 (4)	139
C2—H2···Cg1^iv	0.93	2.91	3.774 (3)	154
C4—H4···Cg1^v	0.93	2.67	3.377 (3)	134

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x+1, y, z; (iv) −x+1, −y+1, −z; (v) x, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₇N₃O₃S₃·CH₄O
M_r	569.74
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.9644 (17), 14.9129 (8), 15.467 (2)
β (°)	91.733 (7)
V (Å³)	2758.4 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.78
Crystal size (mm)	0.52 × 0.42 × 0.06

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.296, 0.842
No. of measured, independent and observed [I > 2σ(I)] reflections	5226, 5226, 4156
R_int	0
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.150, 1.09
No. of reflections	5226
No. of parameters	347
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.32

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), 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
O1L—H1L···O27	0.82	2.41	2.804 (7)	110.4
C16—H16A···O36ⁱ	0.96	2.47	3.348 (4)	152
C16—H16B···S20	0.96	2.68	3.420 (3)	135
C18—H18B···S29	0.96	2.79	3.515 (3)	133
C25—H25···O7ⁱⁱ	0.93	2.44	3.147 (5)	133
C28—H28A···O7ⁱ	0.97	2.48	3.397 (3)	157
C31—H31···O27ⁱⁱⁱ	0.93	2.35	3.107 (4)	139
C2—H2···Cg1^iv	0.93	2.91	3.774 (3)	154
C4—H4···Cg1^v	0.93	2.67	3.377 (3)	134

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x+1, y, z; (iv) −x+1, −y+1, −z; (v) x, −y−1/2, z−3/2.

Acknowledgements

BRDN thanks the University Grants Commission, India, for a Teacher Fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bovin, D. H. R., Crepon, E. & Zard, S. Z. (1992). Bull. Soc. Chim. Fr. 129, 145–150. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Jebas, S. R., Balasubramanian, T., Ravidurai, B. & Kumaresan, S. (2005). Acta Cryst. E61, o2677–o2678. Web of Science CSD CrossRef IUCr Journals Google Scholar
Katsuyuki, N., Carter, B. J., Xu, J. & Hetch, S. M. (1991). J. Am. Chem. Soc. 113, 5099–5100. Google Scholar
Leonard, F., Barklay, F. A., Brown, E. V., Anderson, F. E. & Green, D. M. (1955). Antibiot. Chemother. pp. 261–264. Google Scholar
Lobana, T. S. & Bhatia, P. K. (1989). J. Sci. Ind. Res. 48, 394–401. CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Ravindran Durai Nayagam, B., Jebas, S. R., Grace, S. & Schollmeyer, D. (2008). Acta Cryst. E64, o409. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Symons, M. C. R. & West, D.-X. (1985). J. Chem. Soc. Dalton Trans. pp. 379–381. CrossRef Web of Science Google Scholar