Crystal structure of methyl (2Z)-2-{[N-(2-formyl­phen­yl)-4-methyl­benzene­sulfonamido]­meth­yl}-3-(4-meth­oxy­phen­yl)prop-2-enoate

Trigunait, A.; Damodharan, K.; Manickam, B.; Krishnasamy, G.

doi:10.1107/S2056989015024172

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages o1088-o1089

https://doi.org/10.1107/S2056989015024172

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Crystal structure of methyl (2Z)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfonamido]methyl}-3-(4-methoxyphenyl)prop-2-enoate

Ankur Trigunait,^a Kannan Damodharan,^b Bakthadoss Manickam ^b and Gunasekaran Krishnasamy ^b ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: gunaunom@gmail.com

Edited by R. F. Baggio, Comisión Nacional de Energía Atómica, Argentina (Received 23 October 2015; accepted 16 December 2015; online 31 December 2015)

In the title compound, C₂₆H₂₅NO₆S, the S atom shows a distorted tetrahedral geometry, with O—S—O [119.46 (9)°] and N—S—C [107.16 (7)°] angles deviating from ideal tetrahedral values, a fact attributed to the Thorpe–Ingold effect. The sulfonyl-bound phenyl ring forms dihedral angles of 41.1 (1) and 83.3 (1)°, respectively, with the formylphenyl and phenyl rings. The dihedral angle between formylphenyl and phenyl rings is 47.6 (1)°. The crystal packing features C—H⋯O hydrogen-bond interactions.

Keywords: crystal structure; sulfonamide; Thorpe–Ingold effect.

CCDC reference: 1442750

1. Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas et al. (1988 ); Mandell & Sande (1992 ). For the antifilarial activity of sulfonamide derivatives, see: Radembino et al. (1997 ); For related structures, see: Ranjith et al. (2009 ); Madhanraj et al. (2011 ). For the Thorpe–Ingold effect, see: Bassindale et al. (1984 ).

2. Experimental

2.1. Crystal data

C₂₆H₂₅NO₆S
M_r = 479.53
Triclinic, $[P \overline 1]$
a = 8.3501 (2) Å
b = 8.4859 (2) Å
c = 17.6814 (4) Å
α = 84.424 (1)°
β = 80.952 (1)°
γ = 80.954 (1)°
V = 1218.52 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.20 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2004 ) T_min = 0.979, T_max = 0.983
23816 measured reflections
5519 independent reflections
4232 reflections with I > 2σ(I)
R_int = 0.028

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.135
S = 1.02
5519 reflections
314 parameters
13 restraints
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1Bⁱ	0.93	2.50	3.397 (7)	162
C15—H15A⋯O6	0.97	2.24	2.7322 (19)	111
C24—H24A⋯O4ⁱⁱ	0.96	2.52	3.341 (3)	143
Symmetry codes: (i) x-1, y, z; (ii) -x+3, -y, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1442750

Crystal structure: contains datablocks I, 2R. DOI: https://doi.org/10.1107/S2056989015024172/bg2572sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015024172/bg2572Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015024172/bg2572Isup3.cml

checkCIF report

Comment top

Sulfonamide drugs are widely used for the treatment of certain infections caused by Gram-positive and Gram-negative micro-organisms, some fungi, and certain protozoa (Korolkovas et al., 1988, Mandell & Sande 1992). One of the Sulfonamide derivatives (epoxysulphonamides and ethynesulphonamides) shows anti-filarial activity (Radembino et al., 1997). In view of this biological importance, the crystal structure of the title compound has been determined and the results are presented here. The molecular structure of the title compound is shown in Fig. 1.The S1 atom shows a distorted tetrahedral geometry, with O2—S1—O3 [119.4 (1)°] and N1—S1—C8 [107.1 (1)°] angles deviating from ideal tetrahedral values are attributed to the Thrope-Ingold effect (Bassindale et al., 1984). The sum of bond angles around N1 (348.3°) indicates that N1 is in sp2 hybridization. The sulfonyl bound phenyl (C8–C13) ring forms dihedral angles of 41.1 (1)° and 83.3 (1)°, respectively, with the formyl phenyl (C1–C6) and phenyl (C18—C23) rings. The dihedral angle between formyl phenyl and phenyl rings is 47.6 (1)°. The geometric parameters agree well with those reported for similar structures (Ranjith et al., 2009; Madhanraj et al., 2011). Crystal packing is stabilized by C19—H19···O5 and C24—H24A···O4 inter molecular hydrogen bond interaction. (Shown in Fig.2).

Related literature top

For background to the pharmacological uses of sulfonamides, see: Korolkovas et al. (1988); Mandell & Sande (1992). For antifilarial activity of sulfonamide derivatives, see: Radembino et al. (1997); For related structures, see: Ranjith et al. (2009); Madhanraj et al. (2011). For the Thorpe–Ingold effect, see: Bassindale et al. (1984).

Experimental top

A solution of N-(formylphenyl)(4-methylbenzene)sulfonamide (1 mmol, 0.275 g) and potassium carbonate (1.5 mmol, 0.207 g) in acetonitrile solvent was stirred for 15 min at room temperature. To this solution, methyl(2Z)-2-(bromomethyl)-3-(4-methoxyphenyl)prop-2-enoate (1.2 mmol, 0.342 g) was added dropwise till the addition was complete. After the completion of the reaction, as indicated by TLC, acetonitrile was evaporated. EtOAc (15 ml) and water (15 ml) were added to the crude mass. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product, which was purified through pad of silica gel (100–200mesh) using ethylacetate and hexane(1:9) as solvents. The pure title compound was obtained as a colourless solid (0.426 g, 89% yield). Recrystallization was carried out using ethylacetate as solvent.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms
	Fig. 2. Crystal packing diagram. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Methyl (2Z)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfonamido]methyl}-3-(4-methoxyphenyl)prop-2-enoate top

Crystal data top

C₂₆H₂₅NO₆S	Z = 2
M_r = 479.53	F(000) = 504
Triclinic, P1	D_x = 1.307 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3501 (2) Å	Cell parameters from 8834 reflections
b = 8.4859 (2) Å	θ = 2.6–31.2°
c = 17.6814 (4) Å	µ = 0.17 mm⁻¹
α = 84.424 (1)°	T = 293 K
β = 80.952 (1)°	Block, colourless
γ = 80.954 (1)°	0.25 × 0.20 × 0.20 mm
V = 1218.52 (5) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	5519 independent reflections
Radiation source: fine-focus sealed tube	4232 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and φ scan	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −10→10
T_min = 0.979, T_max = 0.983	k = −11→11
23816 measured reflections	l = −22→22

Refinement top

Refinement on F²	13 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0713P)² + 0.275P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
5519 reflections	Δρ_max = 0.34 e Å⁻³
314 parameters	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₆H₂₅NO₆S	γ = 80.954 (1)°
M_r = 479.53	V = 1218.52 (5) Å³
Triclinic, P1	Z = 2
a = 8.3501 (2) Å	Mo Kα radiation
b = 8.4859 (2) Å	µ = 0.17 mm⁻¹
c = 17.6814 (4) Å	T = 293 K
α = 84.424 (1)°	0.25 × 0.20 × 0.20 mm
β = 80.952 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5519 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2004)	4232 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.983	R_int = 0.028
23816 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	13 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	Δρ_max = 0.34 e Å⁻³
5519 reflections	Δρ_min = −0.36 e Å⁻³
314 parameters

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.

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)
S1	0.89631 (5)	0.51292 (5)	0.33325 (2)	0.04835 (15)
O1A	1.4384 (2)	0.5552 (4)	0.2246 (2)	0.1151 (13)	0.740 (4)
H7A	1.2277	0.5012	0.2267	0.080*	0.740 (4)
O1B	1.3729 (9)	0.4953 (8)	0.2764 (4)	0.1151 (13)	0.260 (4)
H7B	1.2365	0.5460	0.1946	0.080*	0.260 (4)
O2	0.82045 (18)	0.40111 (14)	0.30104 (8)	0.0609 (4)
O3	1.04550 (18)	0.46004 (16)	0.36347 (8)	0.0696 (4)
O4	1.35510 (18)	0.15273 (16)	0.03718 (9)	0.0700 (4)
O5	0.83811 (19)	1.06484 (15)	0.08082 (8)	0.0693 (4)
O6	0.66997 (15)	1.02738 (14)	0.18898 (7)	0.0565 (3)
N1	0.93431 (15)	0.65272 (14)	0.26408 (7)	0.0379 (3)
C1	1.03147 (19)	0.76893 (18)	0.27928 (9)	0.0396 (3)
C2	0.9569 (2)	0.9142 (2)	0.30551 (11)	0.0525 (4)
H2	0.8432	0.9362	0.3149	0.063*
C3	1.0505 (3)	1.0272 (2)	0.31794 (13)	0.0677 (6)
H3	0.9996	1.1253	0.3352	0.081*
C4	1.2173 (3)	0.9952 (3)	0.30501 (14)	0.0720 (6)
H4	1.2801	1.0710	0.3139	0.086*
C5	1.2920 (2)	0.8516 (3)	0.27898 (12)	0.0651 (5)
H5	1.4059	0.8307	0.2703	0.078*
C6	1.2016 (2)	0.7363 (2)	0.26528 (10)	0.0494 (4)
C7	1.2889 (2)	0.5845 (3)	0.23465 (13)	0.0674 (6)
C8	0.7539 (2)	0.6044 (2)	0.40537 (9)	0.0493 (4)
C9	0.5901 (2)	0.6237 (2)	0.39958 (11)	0.0587 (5)
H9	0.5535	0.5855	0.3588	0.070*
C10	0.4797 (3)	0.7018 (3)	0.45622 (13)	0.0703 (6)
H10	0.3682	0.7165	0.4528	0.084*
C11	0.5324 (3)	0.7579 (2)	0.51727 (12)	0.0702 (6)
C12	0.6966 (4)	0.7339 (3)	0.52188 (13)	0.0793 (7)
H12	0.7333	0.7691	0.5634	0.095*
C13	0.8076 (3)	0.6594 (3)	0.46667 (11)	0.0678 (6)
H13	0.9190	0.6457	0.4703	0.081*
C14	0.4101 (4)	0.8423 (3)	0.57835 (16)	0.1047 (10)
H14A	0.3053	0.8683	0.5608	0.157*
H14B	0.4473	0.9388	0.5882	0.157*
H14C	0.4002	0.7734	0.6247	0.157*
C15	0.79663 (18)	0.71501 (18)	0.22006 (9)	0.0401 (3)
H15A	0.7147	0.7856	0.2509	0.048*
H15B	0.7455	0.6265	0.2089	0.048*
C16	0.85673 (19)	0.80473 (18)	0.14613 (9)	0.0392 (3)
C17	0.9703 (2)	0.74544 (19)	0.08975 (9)	0.0430 (4)
H17	0.9941	0.8196	0.0488	0.052*
C18	1.0633 (2)	0.58688 (19)	0.08059 (9)	0.0424 (4)
C19	1.2034 (2)	0.5730 (2)	0.02594 (10)	0.0524 (4)
H19	1.2334	0.6645	−0.0027	0.063*
C20	1.2982 (2)	0.4287 (2)	0.01316 (12)	0.0587 (5)
H20	1.3920	0.4232	−0.0232	0.070*
C21	1.2547 (2)	0.2907 (2)	0.05425 (11)	0.0507 (4)
C22	1.1149 (2)	0.2998 (2)	0.10759 (10)	0.0521 (4)
H22	1.0840	0.2076	0.1351	0.062*
C23	1.0211 (2)	0.4462 (2)	0.12001 (10)	0.0489 (4)
H23	0.9265	0.4510	0.1559	0.059*
C24	1.3116 (3)	0.0075 (2)	0.07567 (14)	0.0790 (7)
H24A	1.3916	−0.0803	0.0580	0.119*
H24B	1.2059	−0.0071	0.0650	0.119*
H24C	1.3080	0.0117	0.1300	0.119*
C25	0.7907 (2)	0.97716 (19)	0.13359 (9)	0.0445 (4)
C26	0.6048 (3)	1.1955 (2)	0.18269 (14)	0.0693 (6)
H26A	0.5197	1.2190	0.2250	0.104*
H26B	0.5607	1.2211	0.1353	0.104*
H26C	0.6908	1.2579	0.1836	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0578 (3)	0.0350 (2)	0.0469 (2)	0.00262 (17)	−0.00629 (19)	0.00590 (16)
O1A	0.0336 (12)	0.118 (2)	0.199 (3)	0.0111 (12)	−0.0125 (15)	−0.082 (2)
O1B	0.0336 (12)	0.118 (2)	0.199 (3)	0.0111 (12)	−0.0125 (15)	−0.082 (2)
O2	0.0854 (10)	0.0349 (6)	0.0604 (8)	−0.0140 (6)	−0.0004 (7)	−0.0018 (5)
O3	0.0716 (9)	0.0610 (8)	0.0674 (8)	0.0168 (7)	−0.0208 (7)	0.0137 (7)
O4	0.0663 (9)	0.0500 (7)	0.0866 (10)	0.0013 (6)	0.0017 (8)	−0.0059 (7)
O5	0.0902 (10)	0.0450 (7)	0.0628 (8)	−0.0074 (7)	0.0068 (7)	0.0127 (6)
O6	0.0576 (8)	0.0441 (6)	0.0602 (8)	0.0031 (5)	−0.0009 (6)	0.0047 (6)
N1	0.0368 (7)	0.0346 (6)	0.0406 (7)	−0.0006 (5)	−0.0064 (5)	0.0006 (5)
C1	0.0417 (8)	0.0379 (7)	0.0383 (8)	−0.0002 (6)	−0.0089 (6)	−0.0023 (6)
C2	0.0524 (10)	0.0443 (9)	0.0589 (11)	0.0044 (7)	−0.0095 (8)	−0.0106 (8)
C3	0.0856 (16)	0.0428 (10)	0.0773 (14)	−0.0027 (9)	−0.0198 (12)	−0.0158 (9)
C4	0.0803 (16)	0.0650 (13)	0.0815 (15)	−0.0261 (11)	−0.0252 (12)	−0.0128 (11)
C5	0.0493 (11)	0.0781 (14)	0.0737 (13)	−0.0138 (10)	−0.0171 (10)	−0.0125 (11)
C6	0.0417 (9)	0.0550 (10)	0.0522 (10)	0.0012 (7)	−0.0134 (8)	−0.0104 (8)
C7	0.0425 (10)	0.0754 (13)	0.0857 (15)	0.0117 (9)	−0.0194 (10)	−0.0296 (11)
C8	0.0617 (11)	0.0423 (8)	0.0395 (9)	−0.0038 (7)	−0.0039 (8)	0.0074 (7)
C9	0.0653 (12)	0.0546 (10)	0.0525 (10)	−0.0110 (9)	−0.0007 (9)	0.0058 (8)
C10	0.0643 (13)	0.0620 (12)	0.0742 (14)	−0.0079 (10)	0.0090 (11)	0.0136 (10)
C11	0.0995 (18)	0.0490 (10)	0.0504 (11)	−0.0066 (11)	0.0152 (11)	0.0061 (9)
C12	0.111 (2)	0.0733 (14)	0.0500 (12)	−0.0041 (13)	−0.0071 (12)	−0.0084 (10)
C13	0.0805 (15)	0.0700 (13)	0.0512 (11)	−0.0029 (11)	−0.0138 (10)	−0.0026 (10)
C14	0.134 (2)	0.0742 (16)	0.0836 (17)	−0.0069 (16)	0.0461 (17)	−0.0058 (14)
C15	0.0339 (8)	0.0409 (8)	0.0436 (8)	−0.0044 (6)	−0.0060 (6)	0.0047 (6)
C16	0.0403 (8)	0.0395 (8)	0.0402 (8)	−0.0108 (6)	−0.0108 (7)	0.0022 (6)
C17	0.0499 (9)	0.0417 (8)	0.0394 (8)	−0.0138 (7)	−0.0086 (7)	0.0019 (6)
C18	0.0479 (9)	0.0440 (8)	0.0383 (8)	−0.0126 (7)	−0.0085 (7)	−0.0042 (6)
C19	0.0540 (10)	0.0483 (9)	0.0529 (10)	−0.0127 (8)	0.0003 (8)	0.0023 (8)
C20	0.0481 (10)	0.0584 (11)	0.0652 (12)	−0.0090 (8)	0.0068 (9)	−0.0041 (9)
C21	0.0499 (10)	0.0464 (9)	0.0566 (10)	−0.0042 (7)	−0.0105 (8)	−0.0086 (8)
C22	0.0659 (12)	0.0416 (8)	0.0501 (10)	−0.0156 (8)	−0.0054 (8)	−0.0033 (7)
C23	0.0554 (10)	0.0464 (9)	0.0452 (9)	−0.0158 (7)	0.0026 (8)	−0.0075 (7)
C24	0.0998 (18)	0.0466 (11)	0.0829 (15)	−0.0004 (11)	0.0001 (13)	−0.0043 (10)
C25	0.0486 (9)	0.0414 (8)	0.0442 (9)	−0.0079 (7)	−0.0102 (7)	0.0013 (7)
C26	0.0743 (14)	0.0447 (10)	0.0818 (14)	0.0054 (9)	−0.0061 (11)	−0.0011 (9)

Geometric parameters (Å, º) top

S1—O3	1.4233 (14)	C11—C12	1.368 (3)
S1—O2	1.4259 (14)	C11—C14	1.515 (3)
S1—N1	1.6486 (13)	C12—C13	1.365 (3)
S1—C8	1.7517 (18)	C12—H12	0.9300
O1A—C7	1.222 (3)	C13—H13	0.9300
O1B—C7	1.223 (3)	C14—H14A	0.9600
O4—C21	1.359 (2)	C14—H14B	0.9600
O4—C24	1.419 (3)	C14—H14C	0.9600
O5—C25	1.193 (2)	C15—C16	1.504 (2)
O6—C25	1.339 (2)	C15—H15A	0.9700
O6—C26	1.445 (2)	C15—H15B	0.9700
N1—C1	1.440 (2)	C16—C17	1.340 (2)
N1—C15	1.4891 (18)	C16—C25	1.489 (2)
C1—C2	1.379 (2)	C17—C18	1.454 (2)
C1—C6	1.391 (2)	C17—H17	0.9300
C2—C3	1.382 (3)	C18—C23	1.389 (2)
C2—H2	0.9300	C18—C19	1.392 (2)
C3—C4	1.363 (3)	C19—C20	1.368 (3)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.366 (3)	C20—C21	1.384 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.386 (3)	C21—C22	1.377 (3)
C5—H5	0.9300	C22—C23	1.378 (2)
C6—C7	1.483 (3)	C22—H22	0.9300
C7—H7A	0.9672	C23—H23	0.9300
C7—H7B	0.9933	C24—H24A	0.9600
C8—C9	1.371 (3)	C24—H24B	0.9600
C8—C13	1.383 (3)	C24—H24C	0.9600
C9—C10	1.392 (3)	C26—H26A	0.9600
C9—H9	0.9300	C26—H26B	0.9600
C10—C11	1.378 (3)	C26—H26C	0.9600
C10—H10	0.9300

O3—S1—O2	119.46 (9)	C8—C13—H13	120.1
O3—S1—N1	106.81 (8)	C11—C14—H14A	109.5
O2—S1—N1	106.18 (7)	C11—C14—H14B	109.5
O3—S1—C8	108.18 (9)	H14A—C14—H14B	109.5
O2—S1—C8	108.44 (9)	C11—C14—H14C	109.5
N1—S1—C8	107.16 (7)	H14A—C14—H14C	109.5
C21—O4—C24	117.95 (16)	H14B—C14—H14C	109.5
C25—O6—C26	116.06 (14)	N1—C15—C16	110.86 (12)
C1—N1—C15	116.00 (11)	N1—C15—H15A	109.5
C1—N1—S1	116.79 (10)	C16—C15—H15A	109.5
C15—N1—S1	115.48 (10)	N1—C15—H15B	109.5
C2—C1—C6	119.77 (16)	C16—C15—H15B	109.5
C2—C1—N1	120.41 (14)	H15A—C15—H15B	108.1
C6—C1—N1	119.79 (14)	C17—C16—C25	115.34 (14)
C1—C2—C3	120.25 (18)	C17—C16—C15	126.06 (14)
C1—C2—H2	119.9	C25—C16—C15	118.56 (14)
C3—C2—H2	119.9	C16—C17—C18	132.06 (14)
C4—C3—C2	120.22 (18)	C16—C17—H17	114.0
C4—C3—H3	119.9	C18—C17—H17	114.0
C2—C3—H3	119.9	C23—C18—C19	116.85 (15)
C3—C4—C5	119.86 (19)	C23—C18—C17	125.39 (15)
C3—C4—H4	120.1	C19—C18—C17	117.72 (15)
C5—C4—H4	120.1	C20—C19—C18	121.79 (16)
C4—C5—C6	121.33 (19)	C20—C19—H19	119.1
C4—C5—H5	119.3	C18—C19—H19	119.1
C6—C5—H5	119.3	C19—C20—C21	120.10 (17)
C5—C6—C1	118.57 (16)	C19—C20—H20	119.9
C5—C6—C7	119.11 (17)	C21—C20—H20	119.9
C1—C6—C7	122.31 (16)	O4—C21—C22	124.42 (17)
O1A—C7—C6	121.8 (2)	O4—C21—C20	115.99 (17)
O1B—C7—C6	117.2 (4)	C22—C21—C20	119.57 (16)
O1A—C7—H7A	118.0	C21—C22—C23	119.62 (16)
C6—C7—H7A	120.0	C21—C22—H22	120.2
O1B—C7—H7B	123.3	C23—C22—H22	120.2
C6—C7—H7B	114.0	C22—C23—C18	122.03 (16)
C9—C8—C13	120.62 (18)	C22—C23—H23	119.0
C9—C8—S1	119.52 (15)	C18—C23—H23	119.0
C13—C8—S1	119.85 (16)	O4—C24—H24A	109.5
C8—C9—C10	118.4 (2)	O4—C24—H24B	109.5
C8—C9—H9	120.8	H24A—C24—H24B	109.5
C10—C9—H9	120.8	O4—C24—H24C	109.5
C11—C10—C9	121.3 (2)	H24A—C24—H24C	109.5
C11—C10—H10	119.4	H24B—C24—H24C	109.5
C9—C10—H10	119.4	O5—C25—O6	122.00 (15)
C12—C11—C10	118.6 (2)	O5—C25—C16	125.15 (16)
C12—C11—C14	121.0 (2)	O6—C25—C16	112.85 (13)
C10—C11—C14	120.4 (3)	O6—C26—H26A	109.5
C13—C12—C11	121.3 (2)	O6—C26—H26B	109.5
C13—C12—H12	119.4	H26A—C26—H26B	109.5
C11—C12—H12	119.4	O6—C26—H26C	109.5
C12—C13—C8	119.7 (2)	H26A—C26—H26C	109.5
C12—C13—H13	120.1	H26B—C26—H26C	109.5

O3—S1—N1—C1	−43.28 (13)	C9—C10—C11—C12	−0.7 (3)
O2—S1—N1—C1	−171.79 (11)	C9—C10—C11—C14	−179.89 (19)
C8—S1—N1—C1	72.47 (13)	C10—C11—C12—C13	1.5 (3)
O3—S1—N1—C15	175.04 (11)	C14—C11—C12—C13	−179.3 (2)
O2—S1—N1—C15	46.53 (13)	C11—C12—C13—C8	−1.1 (3)
C8—S1—N1—C15	−69.21 (13)	C9—C8—C13—C12	−0.1 (3)
C15—N1—C1—C2	45.8 (2)	S1—C8—C13—C12	178.51 (16)
S1—N1—C1—C2	−95.71 (16)	C1—N1—C15—C16	54.01 (17)
C15—N1—C1—C6	−132.35 (15)	S1—N1—C15—C16	−164.00 (11)
S1—N1—C1—C6	86.17 (16)	N1—C15—C16—C17	58.9 (2)
C6—C1—C2—C3	0.0 (3)	N1—C15—C16—C25	−118.85 (15)
N1—C1—C2—C3	−178.15 (16)	C25—C16—C17—C18	179.51 (16)
C1—C2—C3—C4	−0.6 (3)	C15—C16—C17—C18	1.7 (3)
C2—C3—C4—C5	0.6 (4)	C16—C17—C18—C23	19.7 (3)
C3—C4—C5—C6	0.0 (4)	C16—C17—C18—C19	−162.71 (17)
C4—C5—C6—C1	−0.6 (3)	C23—C18—C19—C20	−2.0 (3)
C4—C5—C6—C7	178.0 (2)	C17—C18—C19—C20	−179.77 (17)
C2—C1—C6—C5	0.6 (3)	C18—C19—C20—C21	0.9 (3)
N1—C1—C6—C5	178.73 (16)	C24—O4—C21—C22	1.3 (3)
C2—C1—C6—C7	−177.97 (18)	C24—O4—C21—C20	−177.5 (2)
N1—C1—C6—C7	0.2 (3)	C19—C20—C21—O4	179.36 (18)
C5—C6—C7—O1A	3.6 (4)	C19—C20—C21—C22	0.5 (3)
C1—C6—C7—O1A	−177.9 (3)	O4—C21—C22—C23	−179.51 (17)
C5—C6—C7—O1B	66.3 (5)	C20—C21—C22—C23	−0.7 (3)
C1—C6—C7—O1B	−115.1 (5)	C21—C22—C23—C18	−0.4 (3)
O3—S1—C8—C9	−161.09 (14)	C19—C18—C23—C22	1.7 (3)
O2—S1—C8—C9	−30.16 (15)	C17—C18—C23—C22	179.32 (16)
N1—S1—C8—C9	84.07 (15)	C26—O6—C25—O5	−2.3 (3)
O3—S1—C8—C13	20.28 (17)	C26—O6—C25—C16	177.19 (15)
O2—S1—C8—C13	151.21 (15)	C17—C16—C25—O5	−4.8 (3)
N1—S1—C8—C13	−94.56 (15)	C15—C16—C25—O5	173.22 (17)
C13—C8—C9—C10	0.9 (3)	C17—C16—C25—O6	175.70 (14)
S1—C8—C9—C10	−177.74 (13)	C15—C16—C25—O6	−6.3 (2)
C8—C9—C10—C11	−0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1Bⁱ	0.93	2.50	3.397 (7)	162
C15—H15A···O6	0.97	2.24	2.7322 (19)	111
C24—H24A···O4ⁱⁱ	0.96	2.52	3.341 (3)	143

Symmetry codes: (i) x−1, y, z; (ii) −x+3, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1Bⁱ	0.93	2.50	3.397 (7)	162.2
C15—H15A···O6	0.97	2.24	2.7322 (19)	110.6
C24—H24A···O4ⁱⁱ	0.96	2.52	3.341 (3)	143.4

Symmetry codes: (i) x−1, y, z; (ii) −x+3, −y, −z.

Acknowledgements

KG thanks the UGC, India, for financial support.

References

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Volume 71| Part 12| December 2015| Pages o1088-o1089

https://doi.org/10.1107/S2056989015024172

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of methyl (2Z)-2-{[N-(2-formyl­phen­yl)-4-methyl­benzene­sulfonamido]­meth­yl}-3-(4-meth­­oxy­phen­yl)prop-2-enoate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of methyl (2Z)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfonamido]methyl}-3-(4-methoxyphenyl)prop-2-enoate