7-Bromo-3-ethyl-9-phenyl-2-tosyl­pyrrolo[3,4-b]quinoline

Sudha, D.; Chinnakali, K.; Jayagobi, M.; Raghunathan, R.; Fun, H.-K.

doi:10.1107/S1600536807063222

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o134

https://doi.org/10.1107/S1600536807063222

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7-Bromo-3-ethyl-9-phenyl-2-tosylpyrrolo[3,4-b]quinoline

D. Sudha,^a ‡ K. Chinnakali,^a § M. Jayagobi,^b R. Raghunathan ^b and Hoong-Kun Fun ^c ^*

^aDepartment of Physics, Anna University, Chennai 600025, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600025, India, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 18 November 2007; accepted 26 November 2007; online 6 December 2007)

In the title compound, C₂₆H₂₇BrN₂O₂S, the pyrrolidine ring adopts a twist conformation, while the tetrahydropyridine ring is in a half-chair conformation. The two rings are trans-fused. The dihedral angle between the phenyl ring and the sulfonyl-bound benzene ring is 22.83 (7)°. N—H⋯O hydrogen bonds link the molecules into a chain along the b axis, and the chains are cross-linked into a three-dimensional network by a C—H⋯π interaction and a weak π-π interaction between the sulfonyl-bound benzene rings; the centroid–centroid distance is 3.6957 (8) Å.

Related literature

The crystal structure of the title compound is similar to that of its chloro analogue (Sudha et al., 2007 ). For ring puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Duax et al. (1976 ).

Experimental

Crystal data

C₂₆H₂₇BrN₂O₂S
M_r = 511.47
Monoclinic, P 2₁ /c
a = 9.6293 (2) Å
b = 13.4574 (3) Å
c = 20.2179 (4) Å
β = 116.930 (1)°
V = 2335.84 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.88 mm⁻¹
T = 100.0 (1) K
0.58 × 0.52 × 0.34 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.323, T_max = 0.529
58171 measured reflections
14302 independent reflections
9599 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.094
S = 1.01
14302 reflections
294 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.13 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1ⁱ	0.83 (2)	2.33 (2)	3.1381 (14)	162 (2)
C25—H25A⋯O2	0.97	2.49	3.1312 (15)	123
C3—H3⋯Cg1ⁱⁱ	0.98	2.83	3.7921 (12)	168
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z. Cg1 is the centroid of the C4–C9 benzene ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807063222/is2257sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063222/is2257Isup2.hkl

checkCIF report

Comment top

Previously, we have reported the crystal structure of 7-chloro-2-ethyl-5-phenyl-3-tosyl-pyrrolo[3,4-b]quinoline (Sudha et al., 2007). Now we report here the crystal structure of the bromo analogue, the title compound.

Bond lengths and angles are comparable with those in the chloro analogue (Sudha et al., 2007). A superposition of the non-H atoms (except halides) of the title molecule and its chloro analogue (Fig. 2) using XP in SHELXTL (Sheldrick, 1998), gave an r.m.s. deviation of 0.868 Å. In both compounds, the pyrrolidine ring is trans-fused to the tetrahydropyridine ring.

The pyrrolidine ring has a twist conformation; the asymmetry parameters ΔC₂[C2—C10] (Duax et al., 1976) and the puckering parameters q₂ and φ (Cremer & Pople, 1975) are 0.5 (1)°, 0.481 (1) Å and 270.5 (1)°, respectively. The tosyl group is attached to the pyrrolidine ring in a biaxial position. The tetrahydropyridine ring adopts a half-chair conformation, with Q, θ, φ and ΔC₂[C4—C9] values of 0.461 (1) Å, 44.6 (2)°, 269.1 (2)° and 2.4 (2)°, respectively. The phenyl group is attached to the tetrahydropyridine ring in a biaxial position. The C19—C24 phenyl ring forms dihedral angles of 72.42 (3) and 22.83 (7)°, respectively, with the C4—C9 and C12—C17 benzene rings.

As observed in the isomorphous chloro analogue, the screw-related molecules are linked into a chain along the b axis through N—H···O hydrogen bonds and the chains are cross-linked into a three-dimensional framework (Fig. 3) by C—H···π interactions (Table 2) and π-π interactions between the C12—C17 benzene rings of molecules at (x, y, z) and (2 - x, 1 - y, 1 - z) [the centroid-centroid distance is 3.6957 (8) Å].

Related literature top

The crystal structure of the title compound is similar to that of its chloro analogue (Sudha et al., 2007). For ring puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Duax et al. (1976). Cg1 is the centroid of the C4–C9 benzene ring

Experimental top

InCl₃ (20 mol%) was added to a mixture of 2-(N-cinnamyl-N-tosylamino)butanal (1 mmol) and arylamine (1 mmol) in acetonitrile (20 ml). The reaction mixture was stirred at room temperature for 30 min. On completion of the reaction, as indicated by TLC, the mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over Na₂SO₄. The solvent was evaporated in vacuo and the crude product was chromatographed using a hexane-ethyl acetate (8.5:1.5 v/v) mixture to obtain the title compound. The compound was recrystallized from ethyl acetate solution by slow evaporation.

Structure description top

The crystal structure of the title compound is similar to that of its chloro analogue (Sudha et al., 2007). For ring puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Duax et al. (1976). Cg1 is the centroid of the C4–C9 benzene ring

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 80% probability level.
	Fig. 2. Fit of the title molecule (solid lines) with its chloro analogue (Dashed lines). H atoms have been omitted for clarity.
	Fig. 3. Part of the three-dimensional network in the title compound. Dashed and dotted lines indicate N—H···O and C—H···π interactions, respectively. The π-π interaction is shown by a dashed open line. For the sake of clarity, H atoms not involved in the interactions have been omitted.

7-Bromo-3-ethyl-9-phenyl-2-tosylpyrrolo[3,4-b]quinoline top

Crystal data top

C₂₆H₂₇BrN₂O₂S	F(000) = 1056
M_r = 511.47	D_x = 1.454 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5745 reflections
a = 9.6293 (2) Å	θ = 2.4–38.4°
b = 13.4574 (3) Å	µ = 1.88 mm⁻¹
c = 20.2179 (4) Å	T = 100 K
β = 116.930 (1)°	Block, colourless
V = 2335.84 (9) Å³	0.58 × 0.52 × 0.34 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	14302 independent reflections
Radiation source: fine-focus sealed tube	9599 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 8.33 pixels mm^-1	θ_max = 40.0°, θ_min = 2.3°
ω scans	h = −16→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −24→23
T_min = 0.323, T_max = 0.529	l = −36→36
58171 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0418P)² + 0.5198P] where P = (F_o² + 2F_c²)/3
14302 reflections	(Δ/σ)_max = 0.001
294 parameters	Δρ_max = 1.13 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₂₆H₂₇BrN₂O₂S	V = 2335.84 (9) Å³
M_r = 511.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6293 (2) Å	µ = 1.88 mm⁻¹
b = 13.4574 (3) Å	T = 100 K
c = 20.2179 (4) Å	0.58 × 0.52 × 0.34 mm
β = 116.930 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	14302 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	9599 reflections with I > 2σ(I)
T_min = 0.323, T_max = 0.529	R_int = 0.055
58171 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 1.13 e Å⁻³
14302 reflections	Δρ_min = −0.63 e Å⁻³
294 parameters

Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.009166 (12)	0.383484 (9)	−0.061858 (7)	0.01903 (3)
S1	1.10805 (3)	0.50065 (2)	0.342333 (16)	0.01644 (5)
O1	1.16380 (10)	0.60150 (7)	0.35422 (6)	0.02221 (18)
O2	1.21739 (10)	0.42008 (7)	0.36992 (5)	0.02180 (17)
N1	1.00957 (10)	0.48551 (7)	0.25246 (6)	0.01539 (16)
N2	0.70188 (11)	0.31729 (7)	0.13123 (6)	0.01682 (17)
H1N2	0.738 (2)	0.2632 (16)	0.1260 (10)	0.024 (4)*
C1	0.87389 (12)	0.55496 (8)	0.21501 (6)	0.01499 (18)
H1A	0.8835	0.5940	0.1770	0.018*
H1B	0.8642	0.5993	0.2505	0.018*
C2	0.73638 (11)	0.48360 (8)	0.18133 (6)	0.01310 (16)
H2	0.7174	0.4574	0.2217	0.016*
C3	0.58180 (11)	0.52210 (8)	0.12093 (6)	0.01333 (16)
H3	0.6032	0.5603	0.0853	0.016*
C4	0.48065 (12)	0.43277 (8)	0.08039 (6)	0.01331 (16)
C5	0.32017 (12)	0.44516 (8)	0.03642 (6)	0.01504 (17)
H5	0.2750	0.5070	0.0341	0.018*
C6	0.22782 (12)	0.36598 (8)	−0.00374 (6)	0.01598 (18)
C7	0.29217 (13)	0.27321 (9)	−0.00227 (7)	0.01821 (19)
H7	0.2302	0.2211	−0.0305	0.022*
C8	0.45046 (13)	0.25954 (9)	0.04208 (7)	0.01821 (19)
H8	0.4942	0.1974	0.0438	0.022*
C9	0.54584 (12)	0.33745 (8)	0.08428 (6)	0.01469 (17)
C10	0.80650 (12)	0.40097 (8)	0.15527 (6)	0.01407 (17)
H10	0.8271	0.4245	0.1147	0.017*
C11	0.95981 (12)	0.38117 (8)	0.22454 (6)	0.01524 (17)
H11	0.9365	0.3457	0.2607	0.018*
C12	0.97389 (13)	0.48916 (9)	0.37889 (7)	0.01797 (19)
C13	0.93661 (13)	0.39511 (9)	0.39459 (7)	0.0197 (2)
H13	0.9872	0.3392	0.3891	0.024*
C14	0.82254 (14)	0.38560 (11)	0.41864 (7)	0.0231 (2)
H14	0.7998	0.3231	0.4308	0.028*
C15	0.74214 (15)	0.46833 (12)	0.42474 (7)	0.0246 (2)
C16	0.78110 (17)	0.56192 (12)	0.40851 (8)	0.0274 (3)
H16	0.7283	0.6177	0.4125	0.033*
C17	0.89758 (16)	0.57311 (10)	0.38651 (8)	0.0233 (2)
H17	0.9244	0.6360	0.3770	0.028*
C18	0.61530 (19)	0.45797 (15)	0.44829 (10)	0.0352 (3)
H18A	0.6093	0.3901	0.4613	0.053*
H18B	0.5175	0.4774	0.4081	0.053*
H18C	0.6382	0.4998	0.4904	0.053*
C19	0.51164 (12)	0.59192 (8)	0.15662 (6)	0.01492 (18)
C20	0.53584 (13)	0.69413 (9)	0.15655 (7)	0.0195 (2)
H20	0.5836	0.7198	0.1293	0.023*
C21	0.48931 (15)	0.75812 (10)	0.19693 (8)	0.0268 (3)
H21	0.5076	0.8260	0.1971	0.032*
C22	0.41570 (16)	0.72071 (12)	0.23691 (8)	0.0295 (3)
H22	0.3846	0.7634	0.2639	0.035*
C23	0.38881 (16)	0.61938 (12)	0.23646 (8)	0.0281 (3)
H23	0.3378	0.5943	0.2624	0.034*
C24	0.43787 (14)	0.55503 (10)	0.19723 (7)	0.0213 (2)
H24	0.4214	0.4870	0.1981	0.026*
C25	1.08137 (13)	0.32202 (9)	0.21256 (7)	0.0192 (2)
H25A	1.1749	0.3178	0.2595	0.023*
H25B	1.0426	0.2549	0.1982	0.023*
C26	1.12569 (16)	0.36324 (11)	0.15477 (9)	0.0265 (3)
H26A	1.2025	0.3210	0.1513	0.040*
H26B	1.1676	0.4289	0.1689	0.040*
H26C	1.0350	0.3659	0.1075	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01395 (4)	0.02093 (5)	0.01897 (6)	−0.00094 (4)	0.00462 (4)	−0.00109 (4)
S1	0.01233 (9)	0.01608 (11)	0.01730 (12)	−0.00234 (8)	0.00355 (8)	0.00071 (9)
O1	0.0193 (4)	0.0188 (4)	0.0239 (5)	−0.0068 (3)	0.0058 (3)	−0.0019 (3)
O2	0.0137 (3)	0.0224 (4)	0.0233 (4)	0.0014 (3)	0.0031 (3)	0.0035 (3)
N1	0.0130 (3)	0.0142 (4)	0.0165 (4)	0.0004 (3)	0.0046 (3)	0.0013 (3)
N2	0.0143 (3)	0.0113 (4)	0.0230 (5)	0.0005 (3)	0.0068 (3)	−0.0021 (3)
C1	0.0139 (4)	0.0123 (4)	0.0172 (5)	−0.0001 (3)	0.0057 (3)	0.0005 (3)
C2	0.0128 (3)	0.0117 (4)	0.0150 (4)	0.0002 (3)	0.0064 (3)	−0.0001 (3)
C3	0.0136 (4)	0.0126 (4)	0.0143 (4)	0.0000 (3)	0.0067 (3)	−0.0001 (3)
C4	0.0140 (4)	0.0128 (4)	0.0137 (4)	−0.0004 (3)	0.0068 (3)	−0.0002 (3)
C5	0.0151 (4)	0.0150 (4)	0.0150 (5)	0.0005 (3)	0.0067 (3)	0.0001 (3)
C6	0.0140 (4)	0.0170 (5)	0.0155 (5)	−0.0018 (3)	0.0054 (3)	−0.0011 (4)
C7	0.0172 (4)	0.0156 (4)	0.0199 (5)	−0.0028 (3)	0.0067 (4)	−0.0028 (4)
C8	0.0176 (4)	0.0133 (4)	0.0218 (5)	−0.0011 (3)	0.0072 (4)	−0.0024 (4)
C9	0.0147 (4)	0.0131 (4)	0.0163 (5)	0.0001 (3)	0.0070 (3)	0.0000 (3)
C10	0.0128 (4)	0.0126 (4)	0.0166 (5)	0.0002 (3)	0.0064 (3)	−0.0001 (3)
C11	0.0141 (4)	0.0133 (4)	0.0172 (5)	0.0001 (3)	0.0061 (3)	0.0009 (4)
C12	0.0157 (4)	0.0206 (5)	0.0148 (5)	−0.0023 (3)	0.0045 (4)	0.0004 (4)
C13	0.0157 (4)	0.0215 (5)	0.0183 (5)	−0.0002 (3)	0.0045 (4)	0.0045 (4)
C14	0.0195 (5)	0.0283 (6)	0.0191 (5)	−0.0039 (4)	0.0068 (4)	0.0039 (5)
C15	0.0231 (5)	0.0342 (7)	0.0169 (5)	−0.0046 (5)	0.0094 (4)	−0.0031 (5)
C16	0.0328 (6)	0.0282 (7)	0.0260 (7)	−0.0002 (5)	0.0176 (5)	−0.0061 (5)
C17	0.0300 (6)	0.0197 (5)	0.0228 (6)	−0.0022 (4)	0.0141 (5)	−0.0038 (4)
C18	0.0327 (7)	0.0498 (10)	0.0309 (8)	−0.0065 (6)	0.0212 (6)	−0.0053 (7)
C19	0.0133 (4)	0.0147 (4)	0.0157 (5)	0.0018 (3)	0.0056 (3)	−0.0021 (3)
C20	0.0185 (4)	0.0152 (5)	0.0220 (6)	0.0024 (3)	0.0067 (4)	−0.0019 (4)
C21	0.0241 (5)	0.0196 (5)	0.0304 (7)	0.0064 (4)	0.0067 (5)	−0.0080 (5)
C22	0.0244 (5)	0.0361 (7)	0.0248 (6)	0.0097 (5)	0.0084 (5)	−0.0108 (5)
C23	0.0251 (5)	0.0393 (8)	0.0240 (6)	0.0039 (5)	0.0146 (5)	−0.0052 (6)
C24	0.0210 (5)	0.0242 (6)	0.0216 (6)	0.0001 (4)	0.0123 (4)	−0.0023 (4)
C25	0.0162 (4)	0.0161 (5)	0.0244 (6)	0.0032 (3)	0.0083 (4)	0.0012 (4)
C26	0.0230 (5)	0.0265 (6)	0.0361 (8)	0.0056 (4)	0.0188 (5)	0.0046 (5)

Geometric parameters (Å, º) top

Br1—C6	1.9048 (11)	C12—C13	1.3909 (17)
S1—O2	1.4363 (10)	C12—C17	1.3937 (19)
S1—O1	1.4392 (9)	C13—C14	1.3940 (18)
S1—N1	1.6375 (10)	C13—H13	0.93
S1—C12	1.7619 (12)	C14—C15	1.393 (2)
N1—C1	1.5025 (14)	C14—H14	0.93
N1—C11	1.5083 (15)	C15—C16	1.395 (2)
N2—C9	1.3930 (14)	C15—C18	1.505 (2)
N2—C10	1.4408 (14)	C16—C17	1.389 (2)
N2—H1N2	0.83 (2)	C16—H16	0.93
C1—C2	1.5239 (14)	C17—H17	0.93
C1—H1A	0.97	C18—H18A	0.96
C1—H1B	0.97	C18—H18B	0.96
C2—C10	1.5140 (15)	C18—H18C	0.96
C2—C3	1.5260 (14)	C19—C20	1.3952 (16)
C2—H2	0.98	C19—C24	1.3976 (17)
C3—C19	1.5171 (15)	C20—C21	1.3929 (18)
C3—C4	1.5306 (15)	C20—H20	0.93
C3—H3	0.98	C21—C22	1.389 (2)
C4—C5	1.4006 (14)	C21—H21	0.93
C4—C9	1.4145 (15)	C22—C23	1.387 (2)
C5—C6	1.3898 (15)	C22—H22	0.93
C5—H5	0.93	C23—C24	1.3933 (19)
C6—C7	1.3881 (17)	C23—H23	0.93
C7—C8	1.3867 (16)	C24—H24	0.93
C7—H7	0.93	C25—C26	1.5188 (19)
C8—C9	1.4003 (16)	C25—H25A	0.97
C8—H8	0.93	C25—H25B	0.97
C10—C11	1.5294 (15)	C26—H26A	0.96
C10—H10	0.98	C26—H26B	0.96
C11—C25	1.5230 (16)	C26—H26C	0.96
C11—H11	0.98

O2—S1—O1	119.64 (6)	N1—C11—H11	108.4
O2—S1—N1	106.93 (6)	C25—C11—H11	108.4
O1—S1—N1	106.70 (6)	C10—C11—H11	108.4
O2—S1—C12	108.58 (6)	C13—C12—C17	120.60 (12)
O1—S1—C12	107.56 (6)	C13—C12—S1	119.32 (10)
N1—S1—C12	106.77 (5)	C17—C12—S1	119.91 (10)
C1—N1—C11	109.52 (8)	C12—C13—C14	119.25 (12)
C1—N1—S1	114.59 (8)	C12—C13—H13	120.4
C11—N1—S1	117.20 (8)	C14—C13—H13	120.4
C9—N2—C10	116.82 (9)	C15—C14—C13	120.98 (12)
C9—N2—H1N2	117.8 (13)	C15—C14—H14	119.5
C10—N2—H1N2	117.2 (13)	C13—C14—H14	119.5
N1—C1—C2	102.39 (8)	C14—C15—C16	118.77 (12)
N1—C1—H1A	111.3	C14—C15—C18	121.14 (14)
C2—C1—H1A	111.3	C16—C15—C18	120.09 (14)
N1—C1—H1B	111.3	C17—C16—C15	121.01 (13)
C2—C1—H1B	111.3	C17—C16—H16	119.5
H1A—C1—H1B	109.2	C15—C16—H16	119.5
C10—C2—C1	100.61 (8)	C16—C17—C12	119.34 (13)
C10—C2—C3	113.45 (9)	C16—C17—H17	120.3
C1—C2—C3	118.62 (9)	C12—C17—H17	120.3
C10—C2—H2	107.9	C15—C18—H18A	109.5
C1—C2—H2	107.9	C15—C18—H18B	109.5
C3—C2—H2	107.9	H18A—C18—H18B	109.5
C19—C3—C2	108.23 (9)	C15—C18—H18C	109.5
C19—C3—C4	115.39 (9)	H18A—C18—H18C	109.5
C2—C3—C4	108.39 (9)	H18B—C18—H18C	109.5
C19—C3—H3	108.2	C20—C19—C24	118.71 (11)
C2—C3—H3	108.2	C20—C19—C3	119.97 (10)
C4—C3—H3	108.2	C24—C19—C3	120.91 (10)
C5—C4—C9	118.53 (10)	C21—C20—C19	120.71 (13)
C5—C4—C3	119.87 (9)	C21—C20—H20	119.6
C9—C4—C3	121.58 (9)	C19—C20—H20	119.6
C6—C5—C4	120.63 (10)	C22—C21—C20	120.10 (13)
C6—C5—H5	119.7	C22—C21—H21	120.0
C4—C5—H5	119.7	C20—C21—H21	120.0
C7—C6—C5	121.05 (10)	C23—C22—C21	119.70 (12)
C7—C6—Br1	118.84 (8)	C23—C22—H22	120.1
C5—C6—Br1	120.10 (8)	C21—C22—H22	120.1
C8—C7—C6	118.84 (10)	C22—C23—C24	120.29 (14)
C8—C7—H7	120.6	C22—C23—H23	119.9
C6—C7—H7	120.6	C24—C23—H23	119.9
C7—C8—C9	121.34 (11)	C23—C24—C19	120.47 (13)
C7—C8—H8	119.3	C23—C24—H24	119.8
C9—C8—H8	119.3	C19—C24—H24	119.8
N2—C9—C8	118.47 (10)	C26—C25—C11	115.82 (10)
N2—C9—C4	121.95 (10)	C26—C25—H25A	108.3
C8—C9—C4	119.54 (10)	C11—C25—H25A	108.3
N2—C10—C2	109.73 (9)	C26—C25—H25B	108.3
N2—C10—C11	114.21 (9)	C11—C25—H25B	108.3
C2—C10—C11	101.94 (9)	H25A—C25—H25B	107.4
N2—C10—H10	110.2	C25—C26—H26A	109.5
C2—C10—H10	110.2	C25—C26—H26B	109.5
C11—C10—H10	110.2	H26A—C26—H26B	109.5
N1—C11—C25	114.16 (9)	C25—C26—H26C	109.5
N1—C11—C10	101.06 (8)	H26A—C26—H26C	109.5
C25—C11—C10	115.98 (10)	H26B—C26—H26C	109.5

O2—S1—N1—C1	171.86 (8)	C1—N1—C11—C25	140.52 (10)
O1—S1—N1—C1	−59.00 (9)	S1—N1—C11—C25	−86.74 (11)
C12—S1—N1—C1	55.78 (9)	C1—N1—C11—C10	15.29 (11)
O2—S1—N1—C11	41.45 (9)	S1—N1—C11—C10	148.03 (8)
O1—S1—N1—C11	170.58 (8)	N2—C10—C11—N1	−158.08 (9)
C12—S1—N1—C11	−74.64 (9)	C2—C10—C11—N1	−39.82 (10)
C11—N1—C1—C2	14.81 (12)	N2—C10—C11—C25	77.92 (13)
S1—N1—C1—C2	−119.27 (8)	C2—C10—C11—C25	−163.81 (9)
N1—C1—C2—C10	−39.19 (10)	O2—S1—C12—C13	−30.53 (11)
N1—C1—C2—C3	−163.49 (9)	O1—S1—C12—C13	−161.35 (9)
C10—C2—C3—C19	171.06 (9)	N1—S1—C12—C13	84.45 (10)
C1—C2—C3—C19	−71.20 (12)	O2—S1—C12—C17	154.32 (10)
C10—C2—C3—C4	45.25 (12)	O1—S1—C12—C17	23.50 (12)
C1—C2—C3—C4	162.98 (9)	N1—S1—C12—C17	−90.71 (11)
C19—C3—C4—C5	41.53 (14)	C17—C12—C13—C14	−0.47 (18)
C2—C3—C4—C5	163.04 (10)	S1—C12—C13—C14	−175.59 (9)
C19—C3—C4—C9	−140.35 (11)	C12—C13—C14—C15	2.16 (19)
C2—C3—C4—C9	−18.85 (14)	C13—C14—C15—C16	−2.0 (2)
C9—C4—C5—C6	−1.42 (17)	C13—C14—C15—C18	177.98 (13)
C3—C4—C5—C6	176.75 (10)	C14—C15—C16—C17	0.1 (2)
C4—C5—C6—C7	−0.96 (18)	C18—C15—C16—C17	−179.85 (14)
C4—C5—C6—Br1	178.88 (9)	C15—C16—C17—C12	1.5 (2)
C5—C6—C7—C8	2.08 (19)	C13—C12—C17—C16	−1.4 (2)
Br1—C6—C7—C8	−177.76 (10)	S1—C12—C17—C16	173.74 (11)
C6—C7—C8—C9	−0.81 (19)	C2—C3—C19—C20	95.33 (12)
C10—N2—C9—C8	160.86 (11)	C4—C3—C19—C20	−143.08 (11)
C10—N2—C9—C4	−21.63 (16)	C2—C3—C19—C24	−77.22 (12)
C7—C8—C9—N2	176.02 (11)	C4—C3—C19—C24	44.37 (14)
C7—C8—C9—C4	−1.56 (18)	C24—C19—C20—C21	0.84 (17)
C5—C4—C9—N2	−174.85 (11)	C3—C19—C20—C21	−171.88 (11)
C3—C4—C9—N2	7.01 (17)	C19—C20—C21—C22	−1.04 (19)
C5—C4—C9—C8	2.64 (17)	C20—C21—C22—C23	0.0 (2)
C3—C4—C9—C8	−175.50 (11)	C21—C22—C23—C24	1.2 (2)
C9—N2—C10—C2	47.11 (14)	C22—C23—C24—C19	−1.4 (2)
C9—N2—C10—C11	160.83 (10)	C20—C19—C24—C23	0.37 (18)
C1—C2—C10—N2	171.23 (9)	C3—C19—C24—C23	173.02 (11)
C3—C2—C10—N2	−61.01 (12)	N1—C11—C25—C26	−62.22 (14)
C1—C2—C10—C11	49.81 (10)	C10—C11—C25—C26	54.68 (14)
C3—C2—C10—C11	177.58 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.83 (2)	2.33 (2)	3.1381 (14)	162 (2)
C25—H25A···O2	0.97	2.49	3.1312 (15)	123
C3—H3···Cg1ⁱⁱ	0.98	2.83	3.7921 (12)	168

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₇BrN₂O₂S
M_r	511.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.6293 (2), 13.4574 (3), 20.2179 (4)
β (°)	116.930 (1)
V (Å³)	2335.84 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.58 × 0.52 × 0.34

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.323, 0.529
No. of measured, independent and observed [I > 2σ(I)] reflections	58171, 14302, 9599
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.904

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.094, 1.01
No. of reflections	14302
No. of parameters	294
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.13, −0.63

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.83 (2)	2.33 (2)	3.1381 (14)	162 (2)
C25—H25A···O2	0.97	2.49	3.1312 (15)	123
C3—H3···Cg1ⁱⁱ	0.98	2.83	3.7921 (12)	168

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

Footnotes

‡Working at: Department of Physics, R. M. K. Engineering College, R. S. M Nagar, Kavaraipettai 601206, Tamil Nadu, India.

§Additional correspondence author, email: kali@annauniv.edu

Acknowledgements

HKF thanks Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) grant No. 203/PFIZIK/671064.

References

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Sheldrick, G. M. (1998). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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