2-Bromo-3-eth­oxy-3-[4-(methyl­sulfan­yl)phen­yl]-1-[3-(p-tol­yl)-4-sydnon­yl]propan-1-one

Prathap, S.J.; Nooji, S.R.; Kalluraya, B.; Row, T.N.G.

doi:10.1107/S1600536807041931

2-Bromo-3-ethoxy-3-[4-(methylsulfanyl)phenyl]-1-[3-(p-tolyl)-4-sydnonyl]propan-1-one

S. J. Prathap, S. R. Nooji, B. Kalluraya and T. N. G. Row

In the title compound, C₂₁H₂₁BrN₂O₄S, the carbonyl group of the central propan-1-one unit is twisted by 14.7 (4)° from the plane of the cyclic sydnone group (C₂N₂O₂) to which it is attached, and an intramolecular C—H

O contact is formed to the exocyclic O atom of the sydnone group. Intermolecular C—H

O, C—H

S and C—H

π contacts are observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041931/bi2231sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041931/bi2231Isup2.hkl Contains datablock I

CCDC reference: 664196

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.005 Å
R factor = 0.040
wR factor = 0.110
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.07
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    -   C17     ..       6.88 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C4     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C5     = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Sydnones are products of dehydration of N-nitroso-alpha-amino acids (Earl & Mackney, 1935). Although less toxic (Pillai et al., 1993) than the latter, they remain potent porphyrinogenic (Sutherland et al., 1986) and anti-inflammatory (Satyanarayana & Rao, 1995) compounds. They are also known to scavenge free radicals (Narla & Rao, 1995).

The molecular conformation of the title compound is influenced by π conjugation through the C2—C3 bond and an intramolecular C—H···O hydogen bond, resulting in near coplanarity of the atoms H4, C4, C3, C2, C1 and O2 (torsion angle C4/C3/C2/C1 = -14.7 (4)°) (Fig. 1). The crystal structure exhibits C—H···O intermolecular contacts which define dimeric units (Fig. 2 and Table 1). C—H···S contacts exist between adjacent dimers along the b-axis (Fig. 2 and Table 1). Intermolecular C—H···π contacts are also observed.

Related literature top

For related structures see: Abdul Ajees et al. (2002); Balamurugan et al. (2006); Thamotharan et al. (2003). For general literature related to sydnones, see: Earl & Mackney (1935); Narla & Rao (1995); Pillai et al. (1993); Satyanarayana & Rao (1995); Sutherland et al. (1986).

Experimental top

2,3-Dibromo-1-(3-p-tolylsydnon-4-yl)-3-p-thiomethylphenyl-propan-1-one (0.01 mol) was dissolved in ethanol by heating and triethylamine (0.05 mol) in ethanol was added. The clear solution was stirred for 24 h then filtered. The filtrate was left to stand for a few days, then the solid was collected by filtration and recrystallized from ethanol to yield the title compound.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999) and CAMERON (Pearce & Watkin, 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at 50% probability for non-H atoms. The dashed line indicates an intramolecular C—H···O contact.
	Fig. 2. Packing diagram viewed down the b axis. The dotted lines indicate intermolecular contacts.

2-Bromo-3-ethoxy-3-[4-(methylsulfanyl)phenyl]-1-[3-(p-tolyl)-4-sydnonyl]propan-1-one top

Crystal data top

C₂₁H₂₁BrN₂O₄S	F(000) = 1952
M_r = 477.37	D_x = 1.444 Mg m⁻³
Monoclinic, C2/c	Melting point = 398–400 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 24.420 (3) Å	Cell parameters from 1152 reflections
b = 12.3883 (13) Å	θ = 2.1–25.5°
c = 18.3113 (19) Å	µ = 2.00 mm⁻¹
β = 127.564 (1)°	T = 292 K
V = 4391.1 (8) Å³	Block, yellow
Z = 8	0.37 × 0.19 × 0.14 mm

Data collection top

Bruker SMART CCD diffractometer	4028 independent reflections
Radiation source: fine-focus sealed tube	2844 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 25.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→29
T_min = 0.526, T_max = 0.760	k = −14→14
21297 measured reflections	l = −22→22

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0686P)²] where P = (F_o² + 2F_c²)/3
4028 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₁H₂₁BrN₂O₄S	V = 4391.1 (8) Å³
M_r = 477.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.420 (3) Å	µ = 2.00 mm⁻¹
b = 12.3883 (13) Å	T = 292 K
c = 18.3113 (19) Å	0.37 × 0.19 × 0.14 mm
β = 127.564 (1)°

Data collection top

Bruker SMART CCD diffractometer	4028 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2844 reflections with I > 2σ(I)
T_min = 0.526, T_max = 0.760	R_int = 0.030
21297 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.00	Δρ_max = 0.61 e Å⁻³
4028 reflections	Δρ_min = −0.20 e Å⁻³
265 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
Br1	0.129744 (17)	0.37658 (3)	0.35683 (2)	0.08060 (16)
S1	0.40477 (5)	0.71008 (7)	0.60362 (7)	0.0927 (3)
O1	−0.08313 (11)	0.4536 (2)	0.36798 (17)	0.0953 (7)
O2	0.01082 (12)	0.55252 (19)	0.41210 (17)	0.0961 (7)
O3	0.09233 (9)	0.22010 (15)	0.46713 (14)	0.0724 (5)
O4	0.18750 (9)	0.39308 (14)	0.61802 (13)	0.0624 (5)
N1	−0.10169 (14)	0.3481 (3)	0.3577 (2)	0.0883 (8)
N2	−0.04712 (11)	0.2940 (2)	0.38361 (14)	0.0647 (6)
C1	−0.01380 (16)	0.4642 (3)	0.4000 (2)	0.0758 (8)
C2	0.00835 (13)	0.3559 (2)	0.40954 (18)	0.0578 (6)
C3	0.07635 (13)	0.3141 (2)	0.44795 (17)	0.0563 (6)
C4	0.12791 (13)	0.39690 (19)	0.46110 (18)	0.0559 (6)
H4	0.1112	0.4697	0.4586	0.067*
C5	0.19940 (13)	0.38213 (19)	0.55155 (18)	0.0548 (6)
H5	0.2162	0.3092	0.5546	0.066*
C6	0.24287 (16)	0.3559 (3)	0.7073 (2)	0.0831 (9)
H6A	0.2861	0.3860	0.7251	0.100*
H6B	0.2459	0.2779	0.7070	0.100*
C7	0.23095 (19)	0.3895 (3)	0.7747 (2)	0.1050 (13)
H7A	0.2643	0.3551	0.8329	0.158*
H7B	0.1853	0.3686	0.7523	0.158*
H7C	0.2356	0.4664	0.7824	0.158*
C8	0.25044 (12)	0.46434 (19)	0.56521 (16)	0.0515 (6)
C9	0.24604 (13)	0.5709 (2)	0.58355 (18)	0.0573 (6)
H9	0.2119	0.5909	0.5888	0.069*
C10	0.29095 (13)	0.6482 (2)	0.59430 (18)	0.0586 (7)
H10	0.2862	0.7197	0.6051	0.070*
C11	0.34295 (14)	0.6192 (2)	0.58894 (18)	0.0586 (7)
C12	0.34768 (14)	0.5135 (2)	0.57035 (19)	0.0658 (7)
H12	0.3821	0.4933	0.5656	0.079*
C13	0.30206 (13)	0.4374 (2)	0.55881 (18)	0.0620 (7)
H13	0.3061	0.3662	0.5464	0.074*
C14	0.39791 (19)	0.8274 (3)	0.6521 (2)	0.0859 (9)
H14A	0.4305	0.8803	0.6618	0.129*
H14B	0.4076	0.8097	0.7100	0.129*
H14C	0.3519	0.8560	0.6110	0.129*
C15	−0.05548 (12)	0.1771 (2)	0.37652 (17)	0.0617 (7)
C16	−0.07699 (15)	0.1260 (3)	0.4219 (2)	0.0737 (9)
H16	−0.0848	0.1649	0.4582	0.088*
C17	−0.08666 (15)	0.0150 (3)	0.4120 (2)	0.0773 (8)
H17	−0.1015	−0.0203	0.4419	0.093*
C18	−0.07508 (14)	−0.0435 (3)	0.35973 (18)	0.0717 (8)
C19	−0.05431 (16)	0.0108 (3)	0.31505 (19)	0.0750 (8)
H19	−0.0466	−0.0281	0.2786	0.090*
C20	−0.04448 (16)	0.1203 (2)	0.3223 (2)	0.0725 (8)
H20	−0.0306	0.1554	0.2911	0.087*
C21	−0.0857 (2)	−0.1642 (3)	0.3507 (2)	0.0961 (11)
H21A	−0.0941	−0.1889	0.3928	0.144*
H21B	−0.1246	−0.1818	0.2888	0.144*
H21C	−0.0451	−0.1989	0.3648	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0936 (3)	0.0849 (3)	0.0608 (2)	−0.01660 (16)	0.04580 (19)	−0.00885 (15)
S1	0.1017 (6)	0.0901 (6)	0.1243 (7)	−0.0290 (5)	0.0884 (6)	−0.0232 (5)
O1	0.0724 (14)	0.0963 (18)	0.1152 (18)	0.0283 (13)	0.0562 (14)	0.0039 (14)
O2	0.0999 (16)	0.0629 (15)	0.129 (2)	0.0177 (13)	0.0712 (16)	0.0076 (13)
O3	0.0580 (11)	0.0553 (12)	0.0945 (14)	0.0018 (9)	0.0417 (11)	0.0058 (10)
O4	0.0515 (10)	0.0764 (13)	0.0553 (11)	0.0026 (8)	0.0304 (9)	0.0046 (9)
N1	0.0588 (15)	0.101 (2)	0.099 (2)	0.0147 (15)	0.0451 (15)	−0.0009 (17)
N2	0.0478 (13)	0.0880 (18)	0.0532 (13)	0.0064 (12)	0.0281 (11)	−0.0032 (12)
C1	0.070 (2)	0.078 (2)	0.078 (2)	0.0163 (17)	0.0443 (17)	0.0027 (17)
C2	0.0508 (15)	0.0632 (17)	0.0536 (15)	0.0035 (12)	0.0289 (13)	−0.0003 (12)
C3	0.0546 (15)	0.0545 (17)	0.0545 (15)	0.0007 (12)	0.0306 (13)	−0.0016 (12)
C4	0.0561 (15)	0.0491 (15)	0.0582 (15)	0.0006 (11)	0.0327 (13)	−0.0013 (11)
C5	0.0538 (15)	0.0507 (15)	0.0573 (15)	0.0045 (11)	0.0325 (13)	−0.0017 (11)
C6	0.0639 (18)	0.108 (3)	0.0596 (18)	0.0037 (16)	0.0282 (16)	0.0175 (17)
C7	0.087 (2)	0.159 (4)	0.065 (2)	−0.014 (2)	0.044 (2)	0.009 (2)
C8	0.0480 (13)	0.0513 (15)	0.0514 (14)	0.0019 (11)	0.0284 (12)	−0.0024 (11)
C9	0.0535 (14)	0.0597 (16)	0.0645 (16)	0.0020 (13)	0.0389 (13)	−0.0087 (13)
C10	0.0617 (16)	0.0524 (15)	0.0620 (16)	−0.0011 (12)	0.0378 (14)	−0.0082 (12)
C11	0.0612 (16)	0.0628 (17)	0.0561 (16)	−0.0041 (13)	0.0380 (14)	−0.0048 (13)
C12	0.0649 (17)	0.0696 (19)	0.0795 (19)	0.0005 (14)	0.0525 (16)	−0.0103 (15)
C13	0.0637 (16)	0.0539 (16)	0.0721 (18)	0.0046 (13)	0.0434 (15)	−0.0078 (13)
C14	0.100 (2)	0.0644 (19)	0.093 (2)	−0.0192 (18)	0.058 (2)	−0.0040 (17)
C15	0.0443 (14)	0.081 (2)	0.0505 (15)	−0.0072 (13)	0.0240 (13)	−0.0074 (14)
C16	0.0562 (16)	0.115 (3)	0.0531 (16)	0.0031 (16)	0.0348 (14)	0.0014 (16)
C17	0.0709 (18)	0.097 (3)	0.0656 (18)	−0.0126 (17)	0.0423 (16)	0.0062 (17)
C18	0.0614 (16)	0.095 (2)	0.0432 (15)	−0.0177 (15)	0.0239 (13)	−0.0043 (15)
C19	0.085 (2)	0.083 (2)	0.0588 (17)	−0.0221 (17)	0.0447 (16)	−0.0167 (15)
C20	0.0765 (19)	0.090 (2)	0.0631 (18)	−0.0193 (16)	0.0487 (16)	−0.0108 (15)
C21	0.104 (3)	0.092 (2)	0.073 (2)	−0.032 (2)	0.044 (2)	−0.0061 (19)

Geometric parameters (Å, º) top

Br1—C4	1.953 (3)	C9—C10	1.377 (4)
S1—C14	1.764 (3)	C9—H9	0.930
S1—C11	1.767 (3)	C10—C11	1.380 (4)
O1—N1	1.359 (4)	C10—H10	0.930
O1—C1	1.420 (4)	C11—C12	1.376 (3)
O2—C1	1.202 (4)	C12—C13	1.374 (4)
O3—C3	1.210 (3)	C12—H12	0.930
O4—C5	1.420 (3)	C13—H13	0.930
O4—C6	1.421 (3)	C14—H14A	0.960
N1—N2	1.296 (3)	C14—H14B	0.960
C1—C2	1.417 (4)	C14—H14C	0.960
C2—N2	1.366 (3)	C15—C20	1.370 (4)
C2—C3	1.448 (4)	C15—C16	1.377 (4)
C3—C4	1.525 (3)	C15—N2	1.457 (4)
C4—C5	1.516 (4)	C16—C17	1.388 (4)
C4—H4	0.980	C16—H16	0.930
C5—C8	1.508 (3)	C17—C18	1.360 (4)
C5—H5	0.980	C17—H17	0.930
C6—C7	1.489 (5)	C18—C19	1.373 (4)
C6—H6A	0.970	C18—C21	1.510 (5)
C6—H6B	0.970	C19—C20	1.371 (4)
C7—H7A	0.960	C19—H19	0.930
C7—H7B	0.960	C20—H20	0.930
C7—H7C	0.960	C21—H21A	0.960
C8—C13	1.376 (3)	C21—H21B	0.960
C8—C9	1.382 (3)	C21—H21C	0.960

C14—S1—C11	105.46 (14)	C10—C9—H9	119.1
N1—O1—C1	111.0 (2)	C8—C9—H9	119.1
C5—O4—C6	114.0 (2)	C9—C10—C11	119.8 (2)
N2—N1—O1	105.4 (2)	C9—C10—H10	120.1
N1—N2—C2	114.6 (3)	C11—C10—H10	120.1
N1—N2—C15	115.1 (2)	C12—C11—C10	119.0 (2)
C2—N2—C15	130.2 (2)	C12—C11—S1	116.8 (2)
O2—C1—C2	136.8 (3)	C10—C11—S1	124.2 (2)
O2—C1—O1	119.8 (3)	C13—C12—C11	120.6 (2)
C2—C1—O1	103.5 (3)	C13—C12—H12	119.7
N2—C2—C1	105.4 (2)	C11—C12—H12	119.7
N2—C2—C3	124.6 (2)	C12—C13—C8	121.3 (2)
C1—C2—C3	129.6 (3)	C12—C13—H13	119.4
O3—C3—C2	123.8 (2)	C8—C13—H13	119.4
O3—C3—C4	120.8 (2)	S1—C14—H14A	109.5
C2—C3—C4	115.3 (2)	S1—C14—H14B	109.5
C5—C4—C3	112.4 (2)	S1—C14—H14C	109.5
C5—C4—Br1	110.79 (17)	H14A—C14—H14B	109.5
C3—C4—Br1	105.53 (17)	H14A—C14—H14C	109.5
C5—C4—H4	109.3	H14B—C14—H14C	109.5
C3—C4—H4	109.3	C20—C15—C16	121.1 (3)
Br1—C4—H4	109.3	C20—C15—N2	119.8 (3)
O4—C5—C8	112.0 (2)	C16—C15—N2	119.1 (3)
O4—C5—C4	102.9 (2)	C15—C16—C17	118.2 (3)
C8—C5—C4	112.6 (2)	C15—C16—H16	120.9
O4—C5—H5	109.7	C17—C16—H16	120.9
C8—C5—H5	109.7	C18—C17—C16	121.9 (3)
C4—C5—H5	109.7	C18—C17—H17	119.1
O4—C6—C7	109.5 (3)	C16—C17—H17	119.1
O4—C6—H6A	109.8	C17—C18—C19	118.0 (3)
C7—C6—H6A	109.8	C17—C18—C21	120.6 (3)
O4—C6—H6B	109.8	C19—C18—C21	121.4 (3)
C7—C6—H6B	109.8	C20—C19—C18	122.2 (3)
H6A—C6—H6B	108.2	C20—C19—H19	118.9
C6—C7—H7A	109.5	C18—C19—H19	118.9
C6—C7—H7B	109.5	C15—C20—C19	118.6 (3)
H7A—C7—H7B	109.5	C15—C20—H20	120.7
C6—C7—H7C	109.5	C19—C20—H20	120.7
H7A—C7—H7C	109.5	C18—C21—H21A	109.5
H7B—C7—H7C	109.5	C18—C21—H21C	109.5
C13—C8—C9	117.6 (2)	H21A—C21—H21C	109.5
C13—C8—C5	122.0 (2)	C18—C21—H21B	109.5
C9—C8—C5	120.4 (2)	H21A—C21—H21B	109.5
C10—C9—C8	121.7 (2)	H21C—C21—H21B	109.5

C1—O1—N1—N2	1.5 (3)	C9—C10—C11—C12	1.8 (4)
N1—O1—C1—O2	179.3 (3)	C9—C10—C11—S1	−178.8 (2)
N1—O1—C1—C2	−0.9 (3)	C14—S1—C11—C12	−166.6 (2)
O2—C1—C2—N2	179.7 (4)	C14—S1—C11—C10	13.9 (3)
O1—C1—C2—N2	0.0 (3)	C10—C11—C12—C13	−1.1 (4)
O2—C1—C2—C3	6.3 (6)	S1—C11—C12—C13	179.4 (2)
O1—C1—C2—C3	−173.5 (3)	C11—C12—C13—C8	0.2 (4)
N2—C2—C3—O3	−5.5 (4)	C9—C8—C13—C12	0.1 (4)
C1—C2—C3—O3	166.9 (3)	C5—C8—C13—C12	179.2 (2)
N2—C2—C3—C4	173.0 (2)	C20—C15—C16—C17	0.6 (4)
C1—C2—C3—C4	−14.7 (4)	N2—C15—C16—C17	178.1 (2)
O3—C3—C4—C5	−42.9 (3)	C15—C16—C17—C18	0.4 (4)
C2—C3—C4—C5	138.6 (2)	C16—C17—C18—C19	−1.0 (5)
O3—C3—C4—Br1	77.9 (3)	C16—C17—C18—C21	179.6 (3)
C2—C3—C4—Br1	−100.6 (2)	C17—C18—C19—C20	0.6 (5)
C6—O4—C5—C8	−73.9 (3)	C21—C18—C19—C20	180.0 (3)
C6—O4—C5—C4	164.9 (2)	C16—C15—C20—C19	−1.0 (4)
C3—C4—C5—O4	−58.8 (2)	N2—C15—C20—C19	−178.4 (3)
Br1—C4—C5—O4	−176.61 (14)	C18—C19—C20—C15	0.4 (5)
C3—C4—C5—C8	−179.6 (2)	O1—N1—N2—C2	−1.5 (3)
Br1—C4—C5—C8	62.6 (2)	O1—N1—N2—C15	−178.8 (2)
C5—O4—C6—C7	169.5 (2)	C1—C2—N2—N1	1.0 (3)
O4—C5—C8—C13	136.9 (2)	C3—C2—N2—N1	174.8 (3)
C4—C5—C8—C13	−107.6 (3)	C1—C2—N2—C15	177.7 (3)
O4—C5—C8—C9	−43.9 (3)	C3—C2—N2—C15	−8.4 (4)
C4—C5—C8—C9	71.5 (3)	C20—C15—N2—N1	120.7 (3)
C13—C8—C9—C10	0.6 (4)	C16—C15—N2—N1	−56.8 (3)
C5—C8—C9—C10	−178.5 (2)	C20—C15—N2—C2	−56.1 (4)
C8—C9—C10—C11	−1.6 (4)	C16—C15—N2—C2	126.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2	0.98	2.29	3.093 (4)	139
C6—H6A···Cgⁱ	0.97	2.96	3.830	150
C16—H16···S1ⁱⁱ	0.93	2.88	3.763 (4)	159
C21—H21A···O3ⁱⁱⁱ	0.96	2.57	3.506 (4)	165

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁BrN₂O₄S
M_r	477.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	292
a, b, c (Å)	24.420 (3), 12.3883 (13), 18.3113 (19)
β (°)	127.564 (1)
V (Å³)	4391.1 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.00
Crystal size (mm)	0.37 × 0.19 × 0.14

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.526, 0.760
No. of measured, independent and observed [I > 2σ(I)] reflections	21297, 4028, 2844
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.110, 1.00
No. of reflections	4028
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.20

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1999) and CAMERON (Pearce & Watkin, 1993), PLATON (Spek, 2003).