8-[(Hydrazinyl­idene)meth­yl]-4-methyl-2-oxo-2H-chromen-7-yl 4-methyl­benzene­sulfonate

Yuvaraj, H.; Gayathri, D.; Kalkhambkar, R.G.; Kulkarni, G.M.; Bapset, R.M.

doi:10.1107/S1600536810054620

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o323

doi:10.1107/S1600536810054620

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8-[(Hydrazinylidene)methyl]-4-methyl-2-oxo-2H-chromen-7-yl 4-methylbenzenesulfonate

H. Yuvaraj,^a ^* D. Gayathri,^b Rajesh G. Kalkhambkar,^c G. M. Kulkarni ^c and Rajendra M. Bapset ^d

^aSchool of Display and Chemical Engineering, Yeungnam University, Gyeongsan, Gyeoungbuk 712-749, Republic of Korea, ^bInstitute of Structural Biology and Biophysics-2: Molecular Biophysics, Research Centre Jülich, D-52425 Jülich, Germany, ^cDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad 580 001, Karnataka, India, and ^dDepartment of Chemistry, B. K. College, Belgaum 590 001, Karnataka, India
^*Correspondence e-mail: yuvraj_pd@yahoo.co.in

(Received 15 December 2010; accepted 29 December 2010; online 12 January 2011)

In the title compound, C₁₈H₁₆N₂O₅S, the coumarin ring system is nearly planar, with a maximum out-of-plane deviation of 0.078 (1) Å (r.m.s. deviation = 0.046 Å). The dihedral angle between the coumarin ring system and the toluene ring (r.m.s. deviation = 0.004 Å) is 2.77 (1)°. The crystal packing is stabilized by C—H⋯O and N—H⋯O intermolecular hydrogen bonds generating C(8), C(9) and C(11) chains and R₂²(14), R₂²(23) and R₄³(13) ring graph sets.

Related literature

For the biological activity of coumarins, see: Kulkarni et al. (2006 ); Kalkhambkar et al. (2008 ); Laakso et al. (1994 ); Nofal et al. (2000 ). For related structures, see: Kokila et al. (1995 ); Vasudevan et al. (1990 ). For graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₆N₂O₅S
M_r = 372.39
Monoclinic, P 2₁ /n
a = 9.1947 (3) Å
b = 16.1867 (4) Å
c = 11.6538 (3) Å
β = 99.670 (1)°
V = 1709.81 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.2 × 0.19 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
26334 measured reflections
4260 independent reflections
3285 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.116
S = 1.04
4260 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5ⁱ	0.86	2.59	3.303 (2)	141
N2—H2B⋯O1ⁱⁱ	0.86	2.27	3.045 (2)	150
C10—H10⋯O4ⁱⁱⁱ	0.93	2.55	3.469 (2)	169
C16—H16A⋯O4ⁱⁱ	0.96	2.55	3.405 (3)	149
C18—H18⋯O1^iv	0.93	2.53	3.166 (2)	126
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x+1, y, z; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054620/si2319sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054620/si2319Isup2.hkl

checkCIF report

Comment top

Coumarins represent a group of naturally occurring lactones, whose potential as anti-inflammatory, anti-microbial, anticancer and protease inhibiting agents has recently been reviewed (Kulkarni et al., 2006). Coumarin derivatives with various substituents at the C-4 position with their biological activities have been reported from our laboratory (Kalkhambkar et al., 2008). Many natural coumarins are reported for their wide range of biological and antitumor properties (Nofal et al., 2000). Solid-state conformations of 4-aryloxymethyl and 4-aryl aminomethyl coumarins have been found to be significantly different. The former exhibits a centro-symmetric nature (Vasudevan et al., 1990) in the solid state, whereas the latter have been found to exhibit a layer like structure stabilized by inter molecular hydrogen bonds (Kokila et al., 1995). In view of biological importance of coumarin we synthesized the title compound and report here its structure.

The molecular structure of the title compound is shown in Fig.1. The coumarin ring system is nearly planar with a maximum out-of-plane deviation of 0.078 (1) Å (r.m.s. deviation = 0.046 Å). The dihedral angle between the coumarin ring system and the toluene ring (r.m.s. deviation = 0.004 Å) is 2.77 (1)°. Atoms O1 and C4 lie 0.066 (2) and 0.005 (2) Å, respectively, below the least-squares plane of the atoms (C1/C2/C3/C5/C6/O2). Atom C16 lies -0.008 (2) Å from the least-squares plane of the ring to which it is attached. Torsion angle C8—C7—C11—N1 (-15.2 (2)°) indicates slight deviation of hydrazonomethyl group from the plane of benzo-ring in coumarin moeity.

The crystal packing is stabilized by N—H···O and C—H···O intermolecular hydrogen bonds. N2—H2A···O5ⁱ, C18—H18···O1^iv; N2—H2B···O1ⁱⁱ, C16—H16A···O4ⁱⁱ generate chains of C(9), C(11) {along [010]}; C(9), C(8) {along [100]}, respectively. These intermolecular hydrogen bonds, in turn, generate R₂²(14), R₂²(23) and R₄³(13) graph sets (Bernstein et al., 1995) (Table 1, Fig. 2). The crystal packing is further stabilized by C10—H10···O4ⁱⁱⁱ intermolecular hydrogen bond generating C(8) chain along ac plane. The glide plane symmetry operation and translation along the a axis link the molecules into a three-dimensional network via intermolecular hydrogen bonds (Fig. 3).

Related literature top

For the biological activity of coumarins, see: Kulkarni et al. (2006); Kalkhambkar et al. (2008); Laakso et al. (1994); Nofal et al. (2000). For related structures, see: Kokila et al. (1995); Vasudevan et al. (1990). For graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995).

For related literature, see:

Experimental top

A mixture of toluene-4-sulfonicacid-8-formyl-4-methyl-2-oxo-2H-chromen- 7-ylester (6 mmol), and hydrazine hydrate (6 mmol) in 20 ml of ethanol- acetic acid mixture (2:1) was refluxed on water bath for 6 h. Once the reaction was over, the excess of solvent was removed under reduced pressure and filtered the separated solids. The solids were then washed with excess of cold water, dried and crystallized from ethanol and dioxan mixture. Yield: 78%; Colorless crystalline solid (ethanol); mp 160–162 °C; R_f 0.66 (benzene); IR (KBr) cm^-1 3405, 1724, 1627, 1341; ¹H NMR (CDCl₃ + TFA) δ 2.37 (3H, s), 2.54 (3H, s), 6.47 (1H, s), 7.34 (2H, s), 7.47 (6H, m), 8.68 (1H, s); Anal.Calc.for C₁₈H₁₆N₂O₅S: C, 58.05; H, 4.33; N, 7.52; Found: C, 57.91; H, 4.20; N, 7.27.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The molecular packing of (I) showing the ring graph sets generated by N—H···O and C—H···O intermolecular interactions. For clarity, hydrogen atoms which are not involved in hydrogen bonding are omitted.
	Fig. 3. The molecular packing of (I) showing C10—H10···O4 intermolecular interaction. For clarity, hydrogen atoms which are not involved in hydrogen bonding are omitted.

8-[(Hydrazinylidene)methyl]-4-methyl-2-oxo-2H-chromen-7-yl 4-methylbenzenesulfonate top

Crystal data top

C₁₈H₁₆N₂O₅S	F(000) = 776
M_r = 372.39	D_x = 1.447 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7131 reflections
a = 9.1947 (3) Å	θ = 2.2–27.3°
b = 16.1867 (4) Å	µ = 0.22 mm⁻¹
c = 11.6538 (3) Å	T = 293 K
β = 99.670 (1)°	Plate, colorless
V = 1709.81 (8) Å³	0.2 × 0.19 × 0.19 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3285 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 28.3°, θ_min = 2.2°
phi and ω scans	h = −12→12
26334 measured reflections	k = −21→21
4260 independent reflections	l = −15→15

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) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0548P)² + 0.5733P] where P = (F_o² + 2F_c²)/3
4260 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O₅S	V = 1709.81 (8) Å³
M_r = 372.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.1947 (3) Å	µ = 0.22 mm⁻¹
b = 16.1867 (4) Å	T = 293 K
c = 11.6538 (3) Å	0.2 × 0.19 × 0.19 mm
β = 99.670 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3285 reflections with I > 2σ(I)
26334 measured reflections	R_int = 0.033
4260 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
4260 reflections	Δρ_min = −0.40 e Å⁻³
237 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
S1	0.87241 (5)	0.20073 (3)	0.74789 (4)	0.04805 (14)
O2	0.40215 (11)	−0.02903 (6)	0.69872 (10)	0.0400 (3)
O3	0.83056 (11)	0.12613 (6)	0.65832 (10)	0.0381 (3)
O1	0.21065 (13)	−0.09419 (7)	0.74469 (14)	0.0591 (4)
O4	0.78108 (16)	0.19431 (11)	0.83435 (14)	0.0793 (5)
O5	0.86864 (16)	0.27548 (8)	0.68331 (17)	0.0777 (5)
C11	0.70098 (16)	−0.02353 (9)	0.74255 (14)	0.0371 (3)
H11	0.6508	−0.0599	0.7837	0.045*
C7	0.61790 (16)	0.04122 (9)	0.67270 (13)	0.0330 (3)
C8	0.67779 (16)	0.11089 (9)	0.62748 (13)	0.0357 (3)
C5	0.37380 (16)	0.09308 (9)	0.57881 (13)	0.0355 (3)
C6	0.46285 (16)	0.03608 (9)	0.64762 (13)	0.0331 (3)
C12	1.05418 (18)	0.17468 (10)	0.80513 (14)	0.0409 (4)
C17	1.3108 (2)	0.20553 (11)	0.83220 (17)	0.0488 (4)
H17	1.3876	0.2392	0.8175	0.059*
C2	0.15966 (17)	0.02146 (10)	0.62033 (15)	0.0416 (4)
H2	0.0578	0.0161	0.6127	0.050*
C9	0.59404 (19)	0.16704 (11)	0.55527 (15)	0.0457 (4)
H9	0.6394	0.2107	0.5234	0.055*
C1	0.25173 (17)	−0.03775 (10)	0.69100 (16)	0.0417 (4)
C4	0.11620 (19)	0.14562 (12)	0.49470 (15)	0.0484 (4)
H4A	0.0150	0.1316	0.4958	0.073*
H4B	0.1342	0.1451	0.4159	0.073*
H4C	0.1363	0.1997	0.5272	0.073*
C3	0.21464 (17)	0.08395 (10)	0.56514 (14)	0.0377 (3)
C10	0.44325 (19)	0.15798 (11)	0.53077 (15)	0.0460 (4)
H10	0.3870	0.1955	0.4817	0.055*
C18	1.16766 (19)	0.22511 (11)	0.78238 (16)	0.0453 (4)
H18	1.1480	0.2712	0.7346	0.054*
C14	1.2259 (2)	0.08804 (12)	0.92495 (17)	0.0524 (4)
H14	1.2454	0.0419	0.9725	0.063*
C13	1.0825 (2)	0.10645 (12)	0.87741 (16)	0.0500 (4)
H13	1.0054	0.0736	0.8935	0.060*
C15	1.34283 (19)	0.13723 (11)	0.90328 (16)	0.0468 (4)
C16	1.4988 (2)	0.11716 (14)	0.9572 (2)	0.0643 (5)
H16A	1.5640	0.1583	0.9351	0.096*
H16B	1.5251	0.0640	0.9306	0.096*
H16C	1.5070	0.1164	1.0404	0.096*
N1	0.83982 (14)	−0.03170 (8)	0.74886 (13)	0.0411 (3)
N2	0.90695 (16)	−0.09370 (10)	0.81607 (14)	0.0519 (4)
H2A	0.8559	−0.1258	0.8526	0.062*
H2B	1.0006	−0.1009	0.8222	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0384 (2)	0.0402 (2)	0.0663 (3)	−0.00432 (16)	0.01104 (19)	−0.01826 (19)
O2	0.0273 (5)	0.0324 (5)	0.0604 (7)	0.0000 (4)	0.0079 (5)	0.0048 (5)
O3	0.0329 (5)	0.0358 (6)	0.0473 (6)	−0.0059 (4)	0.0112 (4)	−0.0073 (5)
O1	0.0357 (6)	0.0406 (7)	0.1039 (11)	−0.0001 (5)	0.0202 (7)	0.0154 (7)
O4	0.0507 (8)	0.1124 (13)	0.0803 (10)	−0.0143 (8)	0.0272 (8)	−0.0508 (10)
O5	0.0566 (9)	0.0329 (7)	0.1361 (15)	−0.0016 (6)	−0.0055 (9)	0.0022 (8)
C11	0.0309 (7)	0.0354 (8)	0.0459 (8)	−0.0009 (6)	0.0084 (6)	0.0008 (6)
C7	0.0311 (7)	0.0332 (7)	0.0355 (7)	−0.0003 (5)	0.0076 (6)	−0.0050 (6)
C8	0.0311 (7)	0.0372 (7)	0.0397 (8)	−0.0035 (6)	0.0084 (6)	−0.0034 (6)
C5	0.0339 (7)	0.0374 (8)	0.0352 (7)	0.0020 (6)	0.0052 (6)	−0.0027 (6)
C6	0.0322 (7)	0.0306 (7)	0.0374 (7)	−0.0006 (5)	0.0085 (6)	−0.0039 (6)
C12	0.0398 (8)	0.0394 (8)	0.0445 (8)	−0.0087 (6)	0.0099 (7)	−0.0108 (7)
C17	0.0415 (9)	0.0480 (9)	0.0580 (10)	−0.0150 (7)	0.0116 (8)	−0.0064 (8)
C2	0.0280 (7)	0.0410 (8)	0.0547 (10)	0.0021 (6)	0.0036 (7)	−0.0080 (7)
C9	0.0455 (9)	0.0460 (9)	0.0467 (9)	−0.0046 (7)	0.0107 (7)	0.0116 (7)
C1	0.0297 (7)	0.0334 (8)	0.0632 (10)	−0.0006 (6)	0.0113 (7)	−0.0047 (7)
C4	0.0412 (9)	0.0561 (10)	0.0459 (9)	0.0102 (8)	0.0012 (7)	0.0019 (8)
C3	0.0340 (7)	0.0396 (8)	0.0381 (8)	0.0050 (6)	0.0024 (6)	−0.0083 (6)
C10	0.0442 (9)	0.0485 (10)	0.0442 (9)	0.0033 (7)	0.0040 (7)	0.0109 (7)
C18	0.0466 (9)	0.0379 (8)	0.0518 (10)	−0.0106 (7)	0.0093 (7)	−0.0047 (7)
C14	0.0549 (11)	0.0502 (10)	0.0505 (10)	−0.0092 (8)	0.0040 (8)	0.0042 (8)
C13	0.0498 (10)	0.0508 (10)	0.0505 (10)	−0.0173 (8)	0.0116 (8)	−0.0010 (8)
C15	0.0433 (9)	0.0492 (10)	0.0481 (9)	−0.0063 (7)	0.0079 (7)	−0.0097 (7)
C16	0.0479 (11)	0.0686 (13)	0.0739 (14)	−0.0012 (9)	0.0030 (10)	−0.0027 (11)
N1	0.0321 (6)	0.0398 (7)	0.0513 (8)	0.0020 (5)	0.0070 (6)	0.0035 (6)
N2	0.0338 (7)	0.0548 (9)	0.0668 (10)	0.0064 (6)	0.0074 (7)	0.0177 (7)

Geometric parameters (Å, º) top

S1—O4	1.4197 (15)	C2—C3	1.342 (2)
S1—O5	1.4222 (16)	C2—C1	1.442 (2)
S1—O3	1.6003 (11)	C2—H2	0.9300
S1—C12	1.7441 (17)	C9—C10	1.376 (2)
O2—C6	1.3742 (18)	C9—H9	0.9300
O2—C1	1.3781 (18)	C4—C3	1.497 (2)
O3—C8	1.4119 (18)	C4—H4A	0.9600
O1—C1	1.203 (2)	C4—H4B	0.9600
C11—N1	1.2732 (19)	C4—H4C	0.9600
C11—C7	1.461 (2)	C10—H10	0.9300
C11—H11	0.9300	C18—H18	0.9300
C7—C8	1.397 (2)	C14—C13	1.374 (3)
C7—C6	1.409 (2)	C14—C15	1.395 (2)
C8—C9	1.382 (2)	C14—H14	0.9300
C5—C6	1.394 (2)	C13—H13	0.9300
C5—C10	1.395 (2)	C15—C16	1.501 (3)
C5—C3	1.453 (2)	C16—H16A	0.9600
C12—C18	1.385 (2)	C16—H16B	0.9600
C12—C13	1.387 (2)	C16—H16C	0.9600
C17—C15	1.383 (3)	N1—N2	1.3561 (19)
C17—C18	1.384 (3)	N2—H2A	0.8600
C17—H17	0.9300	N2—H2B	0.8600

O4—S1—O5	118.24 (11)	O1—C1—C2	126.59 (15)
O4—S1—O3	107.55 (8)	O2—C1—C2	117.10 (14)
O5—S1—O3	108.36 (9)	C3—C4—H4A	109.5
O4—S1—C12	110.73 (10)	C3—C4—H4B	109.5
O5—S1—C12	110.17 (9)	H4A—C4—H4B	109.5
O3—S1—C12	100.20 (7)	C3—C4—H4C	109.5
C6—O2—C1	121.77 (12)	H4A—C4—H4C	109.5
C8—O3—S1	114.70 (9)	H4B—C4—H4C	109.5
N1—C11—C7	122.14 (14)	C2—C3—C5	118.53 (14)
N1—C11—H11	118.9	C2—C3—C4	121.58 (15)
C7—C11—H11	118.9	C5—C3—C4	119.84 (15)
C8—C7—C6	114.76 (13)	C9—C10—C5	120.70 (15)
C8—C7—C11	125.94 (13)	C9—C10—H10	119.7
C6—C7—C11	119.30 (13)	C5—C10—H10	119.7
C9—C8—C7	123.11 (14)	C17—C18—C12	118.61 (17)
C9—C8—O3	117.97 (13)	C17—C18—H18	120.7
C7—C8—O3	118.91 (13)	C12—C18—H18	120.7
C6—C5—C10	117.71 (14)	C13—C14—C15	121.31 (18)
C6—C5—C3	118.63 (14)	C13—C14—H14	119.3
C10—C5—C3	123.60 (14)	C15—C14—H14	119.3
O2—C6—C5	120.98 (13)	C14—C13—C12	119.15 (16)
O2—C6—C7	115.20 (13)	C14—C13—H13	120.4
C5—C6—C7	123.80 (14)	C12—C13—H13	120.4
C18—C12—C13	121.00 (16)	C17—C15—C14	118.17 (17)
C18—C12—S1	119.25 (14)	C17—C15—C16	121.05 (17)
C13—C12—S1	119.67 (13)	C14—C15—C16	120.78 (18)
C15—C17—C18	121.75 (16)	C15—C16—H16A	109.5
C15—C17—H17	119.1	C15—C16—H16B	109.5
C18—C17—H17	119.1	H16A—C16—H16B	109.5
C3—C2—C1	122.85 (14)	C15—C16—H16C	109.5
C3—C2—H2	118.6	H16A—C16—H16C	109.5
C1—C2—H2	118.6	H16B—C16—H16C	109.5
C10—C9—C8	119.70 (15)	C11—N1—N2	117.71 (14)
C10—C9—H9	120.2	N1—N2—H2A	120.0
C8—C9—H9	120.2	N1—N2—H2B	120.0
O1—C1—O2	116.30 (15)	H2A—N2—H2B	120.0

O4—S1—O3—C8	42.38 (14)	C7—C8—C9—C10	3.9 (3)
O5—S1—O3—C8	−86.51 (12)	O3—C8—C9—C10	−174.80 (15)
C12—S1—O3—C8	158.10 (11)	C6—O2—C1—O1	−175.70 (15)
N1—C11—C7—C8	−15.2 (2)	C6—O2—C1—C2	4.0 (2)
N1—C11—C7—C6	165.64 (15)	C3—C2—C1—O1	178.45 (18)
C6—C7—C8—C9	−5.4 (2)	C3—C2—C1—O2	−1.2 (2)
C11—C7—C8—C9	175.39 (15)	C1—C2—C3—C5	−1.0 (2)
C6—C7—C8—O3	173.29 (13)	C1—C2—C3—C4	−178.52 (15)
C11—C7—C8—O3	−5.9 (2)	C6—C5—C3—C2	0.7 (2)
S1—O3—C8—C9	72.10 (16)	C10—C5—C3—C2	−176.51 (16)
S1—O3—C8—C7	−106.67 (13)	C6—C5—C3—C4	178.20 (14)
C1—O2—C6—C5	−4.5 (2)	C10—C5—C3—C4	1.0 (2)
C1—O2—C6—C7	173.91 (13)	C8—C9—C10—C5	0.5 (3)
C10—C5—C6—O2	179.38 (14)	C6—C5—C10—C9	−2.9 (2)
C3—C5—C6—O2	2.0 (2)	C3—C5—C10—C9	174.32 (16)
C10—C5—C6—C7	1.1 (2)	C15—C17—C18—C12	0.2 (3)
C3—C5—C6—C7	−176.24 (14)	C13—C12—C18—C17	0.8 (3)
C8—C7—C6—O2	−175.49 (13)	S1—C12—C18—C17	177.42 (13)
C11—C7—C6—O2	3.8 (2)	C15—C14—C13—C12	1.0 (3)
C8—C7—C6—C5	2.9 (2)	C18—C12—C13—C14	−1.3 (3)
C11—C7—C6—C5	−177.88 (14)	S1—C12—C13—C14	−177.96 (14)
O4—S1—C12—C18	−133.39 (14)	C18—C17—C15—C14	−0.5 (3)
O5—S1—C12—C18	−0.71 (17)	C18—C17—C15—C16	−179.64 (18)
O3—S1—C12—C18	113.30 (14)	C13—C14—C15—C17	0.0 (3)
O4—S1—C12—C13	43.30 (17)	C13—C14—C15—C16	179.07 (19)
O5—S1—C12—C13	175.97 (14)	C7—C11—N1—N2	179.96 (14)
O3—S1—C12—C13	−70.01 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5ⁱ	0.86	2.59	3.303 (2)	141
N2—H2B···O1ⁱⁱ	0.86	2.27	3.045 (2)	150
C10—H10···O4ⁱⁱⁱ	0.93	2.55	3.469 (2)	169
C16—H16A···O4ⁱⁱ	0.96	2.55	3.405 (3)	149
C18—H18···O1^iv	0.93	2.53	3.166 (2)	126

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₅S
M_r	372.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.1947 (3), 16.1867 (4), 11.6538 (3)
β (°)	99.670 (1)
V (Å³)	1709.81 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.2 × 0.19 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	26334, 4260, 3285
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.116, 1.04
No. of reflections	4260
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.40

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5ⁱ	0.86	2.59	3.303 (2)	141
N2—H2B···O1ⁱⁱ	0.86	2.27	3.045 (2)	150
C10—H10···O4ⁱⁱⁱ	0.93	2.55	3.469 (2)	169
C16—H16A···O4ⁱⁱ	0.96	2.55	3.405 (3)	149
C18—H18···O1^iv	0.93	2.53	3.166 (2)	126

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

Acknowledgements

HY acknowledges Yeungnam University for the opportunity to work as a Full-Time Foreign Instructor.

References

Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

8-[(Hydrazinyl­­idene)meth­yl]-4-methyl-2-oxo-2H-chromen-7-yl 4-methyl­benzene­sulfonate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

8-[(Hydrazinylidene)methyl]-4-methyl-2-oxo-2H-chromen-7-yl 4-methylbenzenesulfonate