Crystal structure of methyl 1-allyl-4-methyl-1H-benzo[c][1,2]thia­zine-3-carboxyl­ate 2,2-dioxide

Azotla-Cruz, L.; Shishkina, S.; Ukrainets, I.; Lijanova, I.; Likhanova, N.

doi:10.1107/S2056989016015978

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ISSN: 2056-9890

Volume 72| Part 11| November 2016| Pages 1574-1576

https://doi.org/10.1107/S2056989016015978

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Crystal structure of methyl 1-allyl-4-methyl-1H-benzo[c][1,2]thiazine-3-carboxylate 2,2-dioxide

Liliana Azotla-Cruz,^a Svitlana Shishkina,^b ^* Igor Ukrainets,^c Irina Lijanova ^a and Natalya Likhanova ^d

^aNational Polytechnic Institute, CIITEC, Cerrada Cecati S/N, Colonia Santa Catarina de Azcapotzalco, CP 02250, Mexico, DF, Mexico, ^bSSI `Institute for Single Crystals', National Academy of Sciences of Ukraine, 60 Lenina Avenue, Kharkiv 61001, Ukraine, ^cNational University of Pharmacy, 4 Blyukhera St., Kharkiv 61168, Ukraine, and ^dMexican Institute of Petroleum, Eje Central Lazaro Cardenas Norte 152, Col. San Bartolo Atepehuacan, 07730 Mexico, DF, Mexico
^*Correspondence e-mail: sveta@xray.isc.kharkov.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 5 October 2016; accepted 10 October 2016; online 14 October 2016)

In the title compound, C₁₄H₁₅NO₄S, the dihydrothiazine ring adopts a distorted sofa conformation with the S atom displaced from the mean plane through the N and C ring atoms by 0.767 (1) Å. The allyl substituent (C—C=C) is inclined to this mean plane by 78.5 (7)° and the acetate group [C(=O)—O—C] by 66.5 (3)°. In the crystal, molecules are linked by C—H⋯π interactions forming chains propagating along the a-axis direction.

Keywords: crystal structure; benzothiazine; allyl; C—H⋯π interactions.

CCDC reference: 1508990

1. Chemical context

Alkylation of nitrogen heterocycles, particularly those containing reactive exocyclic groups, always attracts attention with its ambiguity and dependence on a variety of factors. For example, esters of 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids are primarily alkylated exclusively at the 4-OH group (Ukrainets et al., 1996 ). However, methyl 4-hydroxy-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxylates that are structurally close to them easily form mixtures of isomeric 3-C- and 4-O-alkylation products under the same conditions (Ukrainets et al., 2015 ). Consequently, it is quite difficult to predict their behaviour in the alkylation reactions of the esters of 4-methyl-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxylic acids, and the determination of the true structure is essential. It has been found that methyl 4-methyl-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxylate 1 in the K₂CO₃/DMSO system is rapidly alkylated with allyl bromide 2 by the cyclic nitrogen atom, with formation of the main product of the reaction studied viz. compound 3 (see Fig. 1).

Figure 1
The synthesis of the title compound, 3.

2. Structural commentary

The molecular structure of the title compound, 3, is illustrated in Fig. 2. The dihydrothiazine ring adopts a distorted sofa conformation: the puckering parameters (Zefirov et al., 1990 ) are: S = 0.67, Θ = 57.1°, Ψ = 19.0°. Atom S1 deviates from the mean plane of the remaining atoms (N1/C1/C6–C8) by 0.767 (1) Å. The allyl substituent (C—C=C) is inclined to this mean plane by 78.5 (7)° and the acetate group (O=C—O—C) by 66.5 (3)°. Atom N1 has a planar configuration, the sum of the bond angles being 359.1°.

Figure 2
The molecular structure of compound 3, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

The strong steric repulsion between methyl group at the C7 atom and the aromatic ring {there are short intramolecular contacts H5⋯C11 = 2.63 and H11A⋯C5 = 2.47 Å in this fragment [the sum of the van der Waals radii (Zefirov, 1997 ) is 2.87 Å]} causes a disturbance of the conjugation between the π-systems of the aromatic ring and the C7=C8 double bond; the C5—C6—C7—C8 torsion angle is −164.7 (4)°. The ester substituent is twisted relatively to the C7=C8 endocyclic double bond [the C7—C8—C9—O1 torsion angle is 46.0 (7)°], leading to its elongation: the C7=C8 bond length is 1.348 (6) Å as compared to the mean value of 1.326 Å (Bürgi & Dunitz, 1994 ). The methyl group of the ester substituent is located in the ap-position to the C8—C9 bond [C8—C9—O2—C10 = −171.5 (5)°]. The allyl group is orthogonal to the benzothiazine fragment plane while the terminal double bond is synperiplanar to the N1—C12 bond [torsion angles C1—N1—C12—C13 and N1—C12—C13—C14 are 97.2 (5) and 3.5 (8)°, respectively]. The steric repulsion between the allyl substituent and the aromatic cycle (short intramolecular contacts H2⋯C12 = 2.77 Å and H12A⋯C2 = 2.83 Å) results in the elongation of the C1—N1 bond [1.411 (5) Å], compared with the mean value of 1.371 Å (Bürgi & Dunitz, 1994).

3. Supramolecular features

In the crystal, molecules are linked by C—H⋯π interactions, forming chains propagating along the a-axis direction. (Table 1 and Fig. 3). There are no other significant intermolecular interactions in the crystal structure, despite the presence of a number of potential donor and acceptor atoms.

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯Cgⁱ	0.97	2.95	3.576 (5)	123
Symmetry code: (i) $[-x-{\script{1\over 2}}, y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 3
A view along the c axis of the crystal packing of compound 3. The C—H⋯π interactions are represented by dashed lines (see Table 1

) and, for clarity, only H atom H12A (grey ball) is included.

4. Database survey

A search of the Cambridge Structural Database (Version 5.37, update May 2016; Groom et al., 2016 ) for 1H-benzo[c][1,2]thiazine 2,2-dioxide yielded 15 hits. These include the 4-hydroxy analogue of the title compound, viz. methyl 1-allyl-4-hydroxy-1H-benzo[c][1,2]thiazine-3-carboxylate 2,2-dioxide (MINJAW; Shishkina et al., 2013 ). This compound crystallized with two molecules in the asymmetric unit. The conformation of the dihydrothiazine ring in both molecules resembles that in the title compound, which has a distorted sofa conformation. A view of the structural overlap of the three molecules is shown in Fig. 4.

Figure 4
The structural overlap of the two independent molecules of the 4-hydroxy analogue (MINJAW; Shishkina et al., 2013

), and the title compound 3, shown in blue.

5. Synthesis and crystallization

The synthesis of the title compound, 3, is illustrated in Fig. 1. To a solution of 2.53 g (0.01 mol) of methyl 4-methyl-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxylate, 1, in 20 ml DMSO were added 2.07 g (0.015 mol) of K₂CO₃ and the mixture was stirred for 30 min. Allyl bromide (1.81 g, 0.015 mol) was then added and the mixture was stirred for a further 30 min at 298 K. It was then diluted with cold water and acidified with dilute HCl to pH 4. It was extracted with CH₂Cl₂ (3 × 10 ml). The organic extracts were combined and the solvent removed by distillation (at reduced pressure at the end). The residue was dissolved in 20 ml of hot methanol and filtered over charcoal. The resulting solution was then placed in a freezer (253 K) for 24 h, after which crystals of the title compound were harvested (yield 2.55 g, 87%; m.p. 360–362 K).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms could all be located in difference Fourier maps. During refinement they were included in calculated positions and treated as riding: C—H = 0.93–0.97 Å with U_iso = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NO₄S
M_r	293.33
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	10.1970 (7), 18.6174 (12), 7.5136 (5)
V (Å³)	1426.39 (16)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.24
Crystal size (mm)	0.20 × 0.10 × 0.02

Data collection
Diffractometer	Agilent Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis RED; Agilent, 2012 )
T_min, T_max	0.706, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9346, 2425, 2111
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.120, 1.05
No. of reflections	2425
No. of parameters	181
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20
Absolute structure	Flack x determined using 785 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.09 (8)
Computer programs: CrysAlis CCD and CrysAlis RED (Agilent, 2012), SHELXS2014 (Sheldrick, 2008 ), SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2008 ), SHELXL2014 (Sheldrick, 2015 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1508990

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2056989016015978/su5329sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016015978/su5329Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016015978/su5329Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis CCD (Agilent, 2012); cell refinement: CrysAlis CCD (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Methyl 1-allyl-4-methyl-1H-benzo[c][1,2]thiazine-3-carboxylate 2,2-dioxide top

Crystal data top

C₁₄H₁₅NO₄S	D_x = 1.366 Mg m⁻³
M_r = 293.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 2163 reflections
a = 10.1970 (7) Å	θ = 3.8–25.1°
b = 18.6174 (12) Å	µ = 0.24 mm⁻¹
c = 7.5136 (5) Å	T = 293 K
V = 1426.39 (16) Å³	Plate, colourless
Z = 4	0.20 × 0.10 × 0.02 mm
F(000) = 616

Data collection top

Agilent Xcalibur Sapphire3 diffractometer	2425 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2111 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	R_int = 0.056
ω–scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	h = −12→10
T_min = 0.706, T_max = 1.000	k = −22→22
9346 measured reflections	l = −7→8

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0618P)² + 0.1291P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2425 reflections	Δρ_max = 0.19 e Å⁻³
181 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Absolute structure: Flack x determined using 785 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (8)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
S1	0.88243 (9)	0.65549 (5)	0.26457 (17)	0.0457 (3)
O1	0.6502 (4)	0.5240 (2)	0.4865 (7)	0.0975 (14)
O2	0.7649 (4)	0.51032 (18)	0.2347 (6)	0.0801 (11)
O3	0.7789 (3)	0.66144 (16)	0.1376 (5)	0.0645 (9)
O4	1.0109 (3)	0.63899 (17)	0.2033 (4)	0.0590 (9)
N1	0.8881 (3)	0.73110 (17)	0.3775 (5)	0.0457 (8)
C1	0.9692 (4)	0.7307 (2)	0.5295 (6)	0.0443 (9)
C2	1.0333 (4)	0.7933 (3)	0.5818 (7)	0.0559 (11)
H2	1.0205	0.8355	0.5180	0.067*
C3	1.1146 (4)	0.7932 (3)	0.7260 (7)	0.0652 (14)
H3	1.1557	0.8355	0.7611	0.078*
C4	1.1362 (5)	0.7308 (3)	0.8195 (7)	0.0722 (15)
H4	1.1956	0.7305	0.9135	0.087*
C5	1.0705 (5)	0.6690 (3)	0.7747 (8)	0.0605 (11)
H5	1.0837	0.6277	0.8419	0.073*
C6	0.9842 (4)	0.6670 (2)	0.6302 (6)	0.0461 (10)
C7	0.9017 (4)	0.6034 (2)	0.5943 (6)	0.0490 (10)
C8	0.8424 (4)	0.5951 (2)	0.4353 (6)	0.0497 (11)
C9	0.7425 (5)	0.5388 (2)	0.3921 (8)	0.0623 (13)
C10	0.6651 (7)	0.4617 (4)	0.1624 (12)	0.110 (3)
H10A	0.6927	0.4446	0.0478	0.165*
H10B	0.6537	0.4217	0.2415	0.165*
H10C	0.5835	0.4870	0.1506	0.165*
C11	0.8826 (5)	0.5494 (3)	0.7415 (9)	0.0715 (15)
H11A	0.9319	0.5640	0.8442	0.107*
H11B	0.7913	0.5467	0.7717	0.107*
H11C	0.9126	0.5031	0.7025	0.107*
C12	0.7970 (4)	0.7897 (2)	0.3411 (7)	0.0547 (11)
H12A	0.7753	0.8127	0.4530	0.066*
H12B	0.7168	0.7693	0.2936	0.066*
C13	0.8440 (5)	0.8458 (2)	0.2154 (8)	0.0661 (15)
H13	0.7888	0.8848	0.1961	0.079*
C14	0.9528 (6)	0.8455 (3)	0.1316 (9)	0.0829 (18)
H14A	1.0112	0.8076	0.1466	0.099*
H14B	0.9737	0.8832	0.0555	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0486 (5)	0.0440 (5)	0.0446 (5)	−0.0024 (4)	−0.0040 (5)	−0.0029 (5)
O1	0.087 (3)	0.089 (3)	0.116 (4)	−0.038 (2)	0.020 (3)	−0.007 (3)
O2	0.084 (2)	0.063 (2)	0.094 (3)	−0.0162 (18)	−0.005 (2)	−0.028 (2)
O3	0.070 (2)	0.062 (2)	0.062 (2)	−0.0037 (16)	−0.0255 (17)	−0.0033 (16)
O4	0.0587 (18)	0.0636 (19)	0.0546 (19)	−0.0032 (15)	0.0108 (14)	−0.0081 (14)
N1	0.0528 (19)	0.0364 (17)	0.048 (2)	−0.0005 (14)	−0.0052 (15)	−0.0030 (17)
C1	0.044 (2)	0.046 (2)	0.043 (2)	−0.0011 (18)	0.0033 (18)	−0.0031 (18)
C2	0.061 (3)	0.053 (3)	0.053 (3)	−0.008 (2)	0.004 (2)	−0.005 (2)
C3	0.070 (3)	0.075 (3)	0.051 (3)	−0.020 (3)	0.005 (2)	−0.015 (2)
C4	0.075 (3)	0.096 (4)	0.046 (3)	−0.009 (3)	−0.013 (2)	−0.008 (3)
C5	0.070 (3)	0.067 (3)	0.045 (2)	0.005 (2)	−0.009 (3)	0.001 (3)
C6	0.049 (2)	0.047 (2)	0.042 (2)	0.0024 (18)	0.0034 (18)	−0.0002 (18)
C7	0.055 (2)	0.042 (2)	0.050 (3)	0.0070 (18)	0.003 (2)	0.0025 (19)
C8	0.051 (2)	0.038 (2)	0.060 (3)	−0.0031 (18)	0.003 (2)	−0.0031 (19)
C9	0.062 (3)	0.046 (2)	0.079 (4)	−0.009 (2)	0.000 (3)	0.000 (2)
C10	0.112 (5)	0.070 (4)	0.149 (7)	−0.028 (4)	−0.040 (5)	−0.028 (4)
C11	0.093 (4)	0.053 (3)	0.068 (4)	−0.001 (2)	−0.002 (3)	0.014 (3)
C12	0.054 (2)	0.046 (2)	0.064 (3)	0.0025 (19)	−0.001 (2)	0.001 (2)
C13	0.067 (3)	0.051 (3)	0.081 (4)	0.003 (2)	0.000 (3)	0.011 (2)
C14	0.076 (4)	0.090 (4)	0.082 (4)	−0.001 (3)	−0.001 (3)	0.026 (3)

Geometric parameters (Å, º) top

S1—O4	1.422 (3)	C5—H5	0.9300
S1—O3	1.427 (3)	C6—C7	1.477 (6)
S1—N1	1.645 (3)	C7—C8	1.348 (6)
S1—C8	1.754 (4)	C7—C11	1.508 (7)
O1—C9	1.210 (6)	C8—C9	1.497 (6)
O2—C9	1.316 (6)	C10—H10A	0.9600
O2—C10	1.466 (6)	C10—H10B	0.9600
N1—C1	1.411 (5)	C10—H10C	0.9600
N1—C12	1.458 (5)	C11—H11A	0.9600
C1—C2	1.392 (6)	C11—H11B	0.9600
C1—C6	1.415 (6)	C11—H11C	0.9600
C2—C3	1.364 (7)	C12—C13	1.487 (7)
C2—H2	0.9300	C12—H12A	0.9700
C3—C4	1.376 (8)	C12—H12B	0.9700
C3—H3	0.9300	C13—C14	1.276 (8)
C4—C5	1.373 (7)	C13—H13	0.9300
C4—H4	0.9300	C14—H14A	0.9300
C5—C6	1.398 (6)	C14—H14B	0.9300

O4—S1—O3	118.8 (2)	C7—C8—C9	125.3 (4)
O4—S1—N1	108.66 (18)	C7—C8—S1	118.0 (3)
O3—S1—N1	107.72 (19)	C9—C8—S1	116.6 (4)
O4—S1—C8	108.2 (2)	O1—C9—O2	124.8 (5)
O3—S1—C8	111.5 (2)	O1—C9—C8	124.1 (5)
N1—S1—C8	100.3 (2)	O2—C9—C8	111.0 (4)
C9—O2—C10	117.4 (5)	O2—C10—H10A	109.5
C1—N1—C12	122.0 (3)	O2—C10—H10B	109.5
C1—N1—S1	115.7 (3)	H10A—C10—H10B	109.5
C12—N1—S1	121.4 (3)	O2—C10—H10C	109.5
C2—C1—N1	120.0 (4)	H10A—C10—H10C	109.5
C2—C1—C6	120.0 (4)	H10B—C10—H10C	109.5
N1—C1—C6	120.0 (3)	C7—C11—H11A	109.5
C3—C2—C1	120.5 (5)	C7—C11—H11B	109.5
C3—C2—H2	119.7	H11A—C11—H11B	109.5
C1—C2—H2	119.7	C7—C11—H11C	109.5
C2—C3—C4	120.3 (5)	H11A—C11—H11C	109.5
C2—C3—H3	119.9	H11B—C11—H11C	109.5
C4—C3—H3	119.9	N1—C12—C13	116.1 (4)
C5—C4—C3	120.3 (5)	N1—C12—H12A	108.3
C5—C4—H4	119.9	C13—C12—H12A	108.3
C3—C4—H4	119.9	N1—C12—H12B	108.3
C4—C5—C6	121.4 (5)	C13—C12—H12B	108.3
C4—C5—H5	119.3	H12A—C12—H12B	107.4
C6—C5—H5	119.3	C14—C13—C12	126.2 (5)
C5—C6—C1	117.4 (4)	C14—C13—H13	116.9
C5—C6—C7	121.5 (4)	C12—C13—H13	116.9
C1—C6—C7	120.8 (4)	C13—C14—H14A	120.0
C8—C7—C6	120.7 (4)	C13—C14—H14B	120.0
C8—C7—C11	121.0 (4)	H14A—C14—H14B	120.0
C6—C7—C11	118.3 (4)

O4—S1—N1—C1	−60.7 (3)	C1—C6—C7—C8	21.7 (6)
O3—S1—N1—C1	169.5 (3)	C5—C6—C7—C11	17.0 (6)
C8—S1—N1—C1	52.7 (3)	C1—C6—C7—C11	−156.7 (4)
O4—S1—N1—C12	130.1 (3)	C6—C7—C8—C9	−171.1 (4)
O3—S1—N1—C12	0.2 (4)	C11—C7—C8—C9	7.3 (7)
C8—S1—N1—C12	−116.5 (3)	C6—C7—C8—S1	7.8 (6)
C12—N1—C1—C2	−42.8 (5)	C11—C7—C8—S1	−173.9 (4)
S1—N1—C1—C2	147.9 (3)	O4—S1—C8—C7	72.8 (4)
C12—N1—C1—C6	136.3 (4)	O3—S1—C8—C7	−154.8 (3)
S1—N1—C1—C6	−32.9 (5)	N1—S1—C8—C7	−40.9 (4)
N1—C1—C2—C3	−178.4 (4)	O4—S1—C8—C9	−108.2 (4)
C6—C1—C2—C3	2.5 (6)	O3—S1—C8—C9	24.2 (4)
C1—C2—C3—C4	1.2 (7)	N1—S1—C8—C9	138.1 (3)
C2—C3—C4—C5	−3.6 (8)	C10—O2—C9—O1	5.4 (8)
C3—C4—C5—C6	2.4 (8)	C10—O2—C9—C8	−171.5 (5)
C4—C5—C6—C1	1.2 (7)	C7—C8—C9—O1	46.0 (7)
C4—C5—C6—C7	−172.6 (5)	S1—C8—C9—O1	−132.9 (5)
C2—C1—C6—C5	−3.6 (6)	C7—C8—C9—O2	−137.1 (5)
N1—C1—C6—C5	177.2 (4)	S1—C8—C9—O2	44.0 (5)
C2—C1—C6—C7	170.3 (4)	C1—N1—C12—C13	97.2 (5)
N1—C1—C6—C7	−8.9 (6)	S1—N1—C12—C13	−94.2 (4)
C5—C6—C7—C8	−164.7 (4)	N1—C12—C13—C14	3.5 (8)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···Cgⁱ	0.97	2.95	3.576 (5)	123

Symmetry code: (i) −x−1/2, y+3/2, z+1/2.

References

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Volume 72| Part 11| November 2016| Pages 1574-1576

https://doi.org/10.1107/S2056989016015978

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of methyl 1-allyl-4-methyl-1H-benzo[c][1,2]thia­zine-3-carboxyl­ate 2,2-dioxide

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

References

research communications

Crystal structure of methyl 1-allyl-4-methyl-1H-benzo[c][1,2]thiazine-3-carboxylate 2,2-dioxide

3. Supramolecular features