4-Hy­droxy-3,5-dimeth­oxy-N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamo­yl]phen­yl}benzamide methanol monosolvate

Pan, W.-G.; Zhao, Z.-D.; Luo, P.; Lin, C.-W.; Miao, J.-H.

doi:10.1107/S1600536811055991

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o379

doi:10.1107/S1600536811055991

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4-Hydroxy-3,5-dimethoxy-N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}benzamide methanol monosolvate

Wei-Gao Pan,^a,^c Zhi-Dong Zhao,^b Peng Luo,^c Cui-Wu Lin ^b and Jian-Hua Miao ^a ^*

^aGuangxi Botanical Garden of Medicinal Plants, Nanning 530023, People's Republic of China, ^bGuangxi University, College of Chemistry and Chemical Engineering, Nanning 530004, People's Republic of China, and ^cGuangxi Traditional Chinese Medicine University, Nanning 530001, People's Republic of China
^*Correspondence e-mail: jianhuamiaogxyyzwy@yahoo.cn

(Received 20 November 2011; accepted 28 December 2011; online 14 January 2012)

The title compound, C₁₉H₁₉N₃O₇S·CH₃OH, was synthesized from syringic acid and sulfamethoxazole. The benzene rings make a dihedral angle of 41.8 (1)° and the isoxazole ring is twisted by 74.3 (1)° from the central benzene ring. The crystal packing features O—H⋯O and O—H⋯N hydrogen bonds in which the hydroxy groups from the main molecule and methanol solvent molecules serve as donor groups.

Related literature

For the biological activity of syringic acid and sulfamethoxazole, see: Wu et al. (2009 ); Itoh et al. (2009 , 2010 ); Ramachandran & Raja (2010 ); Ma et al. (2007 ); Hida et al. (2005 ); Liu et al. (2003 ). For related structures, see: Camerman et al. (1979 ); Yan et al. (2009 ); Yasmeen et al. (2010 ).

Experimental

Crystal data

C₁₉H₁₉N₃O₇S·CH₄O
M_r = 465.47
Monoclinic, P 2₁ /n
a = 12.133 (11) Å
b = 8.684 (8) Å
c = 20.983 (19) Å
β = 102.043 (13)°
V = 2162 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.35 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.933, T_max = 0.961
11585 measured reflections
3807 independent reflections
2900 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.140
S = 1.05
3807 reflections
298 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N3ⁱ	0.85 (3)	2.05 (3)	2.852 (4)	157 (3)
O8—H8⋯O2ⁱⁱ	0.94 (5)	2.12 (6)	3.004 (4)	156 (5)
O8—H8⋯O1ⁱⁱ	0.94 (5)	2.44 (5)	3.133 (4)	131 (4)
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) x, y-1, z.

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811055991/bh2401sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055991/bh2401Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055991/bh2401Isup3.cml

checkCIF report

Comment top

Syringic acid, a natural compound occurring in many kinds of plant species, was synthesized and used widely in medicine, perfume, pesticide chemistry and organic synthetic industry. Syringic acid showed antifungal activity at high concentration (Wu et al., 2009), anti-endotoxic effects (Liu et al., 2003), hepatoprotective effect (Itoh et al., 2009, 2010; Ramachandran & Raja, 2010). Sulfamethoxazole was usually used as anti-infective (anti-bacterial or anti-fungal) drug (Ma et al., 2007; Hida et al., 2005). Whether the title product (Fig. 1, 2 and 3) shows combined-effects (combining the activities of syringic acid with those of sulfamethoxazole) or has some novel properties should be investigated in future. Some structures closely related to the title compound were previously published, which include the syringic or sulfamethoxazole fragment (Camerman et al., 1979; Yan et al., 2009; Yasmeen et al., 2010).

Related literature top

For the biological activity of syringic acid and sulfamethoxazole, see: Wu et al. (2009); Itoh et al. (2009, 2010); Ramachandran & Raja (2010); Ma et al. (2007); Hida et al. (2005); Liu et al. (2003). For related structures, see: Camerman et al. (1979); Yan et al. (2009); Yasmeen et al. (2010).

Experimental top

4000 mg (20 mmol) of syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) in 30 ml of acetic anhydride was stirred and refluxed at 120 °C for 2 h. 600 ml of water was added to the above solution to get precipitates (3610 mg) by method of pumping filtration. 3000 mg (12 mmol) of above dry precipitates in 20 ml of thionyl chloride was stirred and refluxed at 80 °C for 6 h under anhydrous conditions. The solution was removed under reduced pressure to get residue (3415 mg). 3100 mg (12 mmol) of the residue, 3040 mg (12 mmol) of sulfamethoxazole [4-amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide] and 6 ml of pyridine in 200 ml of THF were stirred at 0 °C for 2 h. and then at room temperature for 24 h. 4000 ml of water was added to the above reaction solution to get 4165 mg of precipitates after pumping filtration. 4000 mg (8.4 mmol) of these precipitates and 20 ml of 10 mmol.mL^-1 hydrochloric acid in 150 ml of THF were stirred and refluxed at 60 °C for 1 h. 3000 ml of water was added to the hydrolytic solution to get product (2720 mg) after pumping filtration. This final synthetic product was detected by electrospray ionization mass spectroscopy (ESI) to give a molecular ion at m/z value of 432.0 ([M—H]^-). This product was redissolved in mixed solution of THF and methanol and then left for evaporating at room temperature. After crystallization and recrystallization from the mixed solution, colorless crystals suitable for X-ray analysis were obtained (mp. 494–495 K).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Synthesis of the title molecule.
	Fig. 2. A view of the title compound, with 30% probability displacement ellipsoids.
	Fig. 3. Crystal packing, viewed along the b axis, of the title complex. The O—H···O, O—H···N and N—H···O interactions are shown as dashed lines.

4-Hydroxy-3,5-dimethoxy-N-{4-[(5-methyl-1,2-oxazol-3- yl)sulfamoyl]phenyl}benzamide methanol monosolvate top

Crystal data top

C₁₉H₁₉N₃O₇S·CH₄O	F(000) = 976
M_r = 465.47	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 494 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.133 (11) Å	Cell parameters from 3807 reflections
b = 8.684 (8) Å	θ = 1.8–25.0°
c = 20.983 (19) Å	µ = 0.20 mm⁻¹
β = 102.043 (13)°	T = 296 K
V = 2162 (3) Å³	Block, colourless
Z = 4	0.35 × 0.24 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3807 independent reflections
Radiation source: fine-focus sealed tube	2900 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→14
T_min = 0.933, T_max = 0.961	k = −10→10
11585 measured reflections	l = −23→24

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0122P)² + 1.2353P] where P = (F_o² + 2F_c²)/3
3807 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³
0 constraints

Crystal data top

C₁₉H₁₉N₃O₇S·CH₄O	V = 2162 (3) Å³
M_r = 465.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.133 (11) Å	µ = 0.20 mm⁻¹
b = 8.684 (8) Å	T = 296 K
c = 20.983 (19) Å	0.35 × 0.24 × 0.20 mm
β = 102.043 (13)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3807 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2900 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.961	R_int = 0.042
11585 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.34 e Å⁻³
3807 reflections	Δρ_min = −0.48 e Å⁻³
298 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.18631 (5)	0.23253 (8)	1.00904 (3)	0.0372 (2)
O1	0.29542 (15)	1.3250 (2)	0.77380 (10)	0.0480 (5)
O2	0.49358 (17)	1.4549 (2)	0.80363 (10)	0.0463 (5)
O3	0.66996 (15)	1.3222 (2)	0.88701 (11)	0.0533 (6)
O4	0.51958 (15)	0.7933 (2)	0.92734 (11)	0.0539 (6)
O5	0.06867 (14)	0.2401 (2)	1.00843 (10)	0.0463 (5)
O6	0.23161 (17)	0.1065 (2)	0.97917 (10)	0.0501 (5)
O7	0.24567 (19)	0.4522 (3)	1.22145 (11)	0.0599 (6)
O8	0.40341 (19)	0.4397 (3)	0.65913 (12)	0.0639 (7)
N1	0.33231 (17)	0.8292 (2)	0.91667 (11)	0.0384 (5)
N2	0.25363 (17)	0.2263 (3)	1.08544 (11)	0.0398 (6)
N3	0.3029 (2)	0.3712 (3)	1.17963 (13)	0.0522 (7)
C1	0.4473 (2)	1.0346 (3)	0.88707 (12)	0.0331 (6)
C2	0.5519 (2)	1.1046 (3)	0.90221 (13)	0.0373 (6)
C3	0.5688 (2)	1.2450 (3)	0.87506 (13)	0.0375 (6)
C4	0.4811 (2)	1.3181 (3)	0.83263 (13)	0.0343 (6)
C5	0.3754 (2)	1.2467 (3)	0.81737 (13)	0.0358 (6)
C6	0.3588 (2)	1.1071 (3)	0.84468 (13)	0.0351 (6)
C7	0.4365 (2)	0.8765 (3)	0.91227 (13)	0.0339 (6)
C8	0.1907 (2)	1.2484 (4)	0.75269 (19)	0.0664 (10)
C9	0.7670 (2)	1.2299 (4)	0.88784 (19)	0.0639 (10)
C10	0.3002 (2)	0.6841 (3)	0.93632 (13)	0.0344 (6)
C11	0.1948 (2)	0.6720 (3)	0.95179 (14)	0.0420 (7)
C12	0.1587 (2)	0.5344 (3)	0.97264 (14)	0.0436 (7)
C13	0.2275 (2)	0.4053 (3)	0.97739 (13)	0.0353 (6)
C14	0.3311 (2)	0.4152 (3)	0.96069 (14)	0.0395 (6)
C15	0.3678 (2)	0.5532 (3)	0.94009 (14)	0.0405 (7)
C16	0.2235 (2)	0.3183 (3)	1.13335 (13)	0.0371 (6)
C17	0.1158 (2)	0.3594 (3)	1.14200 (15)	0.0462 (7)
C18	0.1341 (3)	0.4427 (4)	1.19678 (15)	0.0505 (8)
C19	0.0590 (3)	0.5249 (5)	1.23277 (19)	0.0758 (11)
C20	0.4962 (3)	0.5218 (5)	0.64565 (19)	0.0711 (10)
H1A	0.2792	0.8958	0.9062	0.046*
H2	0.560 (3)	1.487 (4)	0.8163 (16)	0.060 (10)*
H2B	0.3095	0.1639	1.0962	0.048*
H2C	0.6109	1.0569	0.9308	0.045*
H6A	0.2881	1.0608	0.8349	0.042*
H8	0.418 (4)	0.420 (6)	0.704 (3)	0.15 (2)*
H8A	0.1408	1.3128	0.7224	0.100*
H8B	0.1578	1.2274	0.7896	0.100*
H8C	0.2028	1.1534	0.7318	0.100*
H9A	0.8330	1.2939	0.8963	0.096*
H9B	0.7607	1.1802	0.8464	0.096*
H9C	0.7729	1.1534	0.9214	0.096*
H11A	0.1481	0.7579	0.9480	0.050*
H12A	0.0884	0.5278	0.9835	0.052*
H14A	0.3766	0.3284	0.9633	0.047*
H15A	0.4378	0.5590	0.9287	0.049*
H17A	0.0468	0.3343	1.1154	0.055*
H19A	0.1035	0.5718	1.2711	0.114*
H19B	0.0072	0.4531	1.2452	0.114*
H19C	0.0178	0.6030	1.2053	0.114*
H20A	0.4828	0.6303	0.6482	0.107*
H20B	0.5060	0.4965	0.6026	0.107*
H20C	0.5630	0.4944	0.6769	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0342 (4)	0.0333 (4)	0.0451 (4)	−0.0035 (3)	0.0105 (3)	0.0010 (3)
O1	0.0361 (10)	0.0457 (12)	0.0569 (13)	−0.0021 (8)	−0.0024 (9)	0.0198 (10)
O2	0.0402 (11)	0.0386 (12)	0.0569 (13)	−0.0080 (9)	0.0026 (9)	0.0146 (10)
O3	0.0371 (10)	0.0407 (12)	0.0760 (15)	−0.0075 (9)	−0.0018 (10)	0.0086 (11)
O4	0.0326 (10)	0.0447 (12)	0.0844 (16)	0.0043 (9)	0.0120 (10)	0.0239 (11)
O5	0.0321 (10)	0.0499 (13)	0.0566 (13)	−0.0079 (8)	0.0088 (9)	0.0033 (10)
O6	0.0560 (12)	0.0343 (11)	0.0639 (14)	−0.0033 (9)	0.0216 (10)	−0.0088 (10)
O7	0.0644 (14)	0.0680 (16)	0.0474 (13)	−0.0105 (11)	0.0120 (10)	−0.0069 (11)
O8	0.0547 (13)	0.0796 (18)	0.0555 (15)	−0.0104 (12)	0.0071 (11)	−0.0017 (13)
N1	0.0337 (11)	0.0314 (12)	0.0523 (14)	0.0070 (9)	0.0139 (10)	0.0123 (11)
N2	0.0346 (11)	0.0360 (13)	0.0485 (14)	0.0070 (9)	0.0080 (10)	0.0091 (11)
N3	0.0459 (14)	0.0581 (17)	0.0515 (16)	−0.0072 (12)	0.0080 (12)	0.0012 (13)
C1	0.0348 (13)	0.0315 (14)	0.0338 (14)	0.0018 (10)	0.0090 (11)	0.0035 (11)
C2	0.0366 (14)	0.0367 (16)	0.0374 (15)	0.0023 (11)	0.0051 (11)	0.0043 (12)
C3	0.0331 (13)	0.0337 (16)	0.0446 (16)	−0.0044 (11)	0.0057 (11)	0.0012 (12)
C4	0.0390 (14)	0.0283 (14)	0.0362 (14)	−0.0019 (10)	0.0094 (11)	0.0052 (12)
C5	0.0348 (14)	0.0369 (16)	0.0355 (15)	0.0049 (11)	0.0071 (11)	0.0060 (12)
C6	0.0323 (13)	0.0334 (15)	0.0401 (15)	−0.0014 (10)	0.0085 (11)	0.0036 (12)
C7	0.0325 (13)	0.0328 (15)	0.0371 (15)	0.0008 (10)	0.0085 (11)	0.0044 (12)
C8	0.0364 (16)	0.068 (2)	0.086 (3)	−0.0071 (15)	−0.0075 (16)	0.031 (2)
C9	0.0386 (16)	0.069 (2)	0.083 (3)	−0.0101 (15)	0.0116 (16)	−0.004 (2)
C10	0.0341 (13)	0.0337 (15)	0.0360 (14)	0.0015 (11)	0.0084 (11)	0.0064 (12)
C11	0.0307 (13)	0.0395 (16)	0.0573 (18)	0.0095 (11)	0.0125 (12)	0.0133 (14)
C12	0.0294 (13)	0.0449 (18)	0.0584 (19)	0.0023 (11)	0.0135 (12)	0.0104 (14)
C13	0.0342 (13)	0.0365 (15)	0.0356 (15)	−0.0004 (11)	0.0083 (11)	0.0017 (12)
C14	0.0392 (14)	0.0325 (15)	0.0504 (17)	0.0048 (11)	0.0180 (12)	0.0051 (13)
C15	0.0369 (14)	0.0353 (16)	0.0546 (18)	0.0033 (11)	0.0213 (12)	0.0048 (13)
C16	0.0369 (14)	0.0330 (15)	0.0413 (16)	−0.0035 (11)	0.0078 (12)	0.0120 (12)
C17	0.0379 (15)	0.0511 (19)	0.0500 (18)	0.0008 (12)	0.0104 (13)	0.0015 (15)
C18	0.0560 (19)	0.052 (2)	0.0468 (18)	−0.0015 (14)	0.0180 (15)	0.0083 (15)
C19	0.095 (3)	0.073 (3)	0.070 (3)	0.008 (2)	0.040 (2)	−0.002 (2)
C20	0.061 (2)	0.073 (3)	0.080 (3)	−0.0076 (18)	0.0143 (19)	−0.003 (2)

Geometric parameters (Å, º) top

S1—O5	1.426 (2)	C7—C1	1.486 (4)
S1—O6	1.427 (2)	C8—H8C	0.9600
S1—N2	1.641 (3)	C8—H8B	0.9600
S1—C13	1.755 (3)	C8—H8A	0.9600
O1—C5	1.367 (3)	C9—H9C	0.9600
O1—C8	1.420 (4)	C9—H9B	0.9600
O2—C4	1.357 (3)	C9—H9A	0.9600
O2—H2	0.85 (3)	C10—C15	1.394 (4)
O3—C3	1.374 (3)	C10—C11	1.388 (4)
O3—C9	1.421 (4)	C11—H11A	0.9300
O4—C7	1.227 (3)	C11—C12	1.375 (4)
O7—C18	1.347 (4)	C12—H12A	0.9300
O7—N3	1.415 (3)	C13—C12	1.389 (4)
O8—C20	1.410 (4)	C13—C14	1.376 (4)
O8—H8	0.94 (5)	C14—H14A	0.9300
N1—C7	1.350 (3)	C14—C15	1.379 (4)
N1—C10	1.406 (3)	C15—H15A	0.9300
N1—H1A	0.8600	C16—C17	1.403 (4)
N2—C16	1.392 (4)	C16—N3	1.301 (4)
N2—H2B	0.8600	C17—H17A	0.9300
C2—H2C	0.9300	C17—C18	1.337 (4)
C2—C1	1.383 (4)	C18—C19	1.482 (4)
C2—C3	1.379 (4)	C19—H19C	0.9600
C4—C5	1.400 (4)	C19—H19B	0.9600
C4—C3	1.391 (4)	C19—H19A	0.9600
C6—H6A	0.9300	C20—H20C	0.9600
C6—C1	1.394 (4)	C20—H20B	0.9600
C6—C5	1.373 (4)	C20—H20A	0.9600

S1—N2—H2B	118.8	C7—N1—C10	127.9 (2)
O1—C8—H8A	109.5	C10—C11—H11A	119.7
O1—C8—H8B	109.5	C10—C15—H15A	120.0
O1—C5—C6	124.9 (2)	C10—N1—H1A	116.1
O1—C5—C4	114.9 (2)	C11—C12—H12A	120.1
O1—C8—H8C	109.5	C11—C12—C13	119.9 (2)
O2—C4—C3	123.0 (2)	C11—C10—N1	117.5 (2)
O2—C4—C5	117.9 (2)	C11—C10—C15	119.0 (2)
O3—C9—H9A	109.5	C12—C11—H11A	119.7
O3—C9—H9B	109.5	C12—C11—C10	120.7 (2)
O3—C9—H9C	109.5	C12—C13—S1	120.2 (2)
O3—C3—C2	124.1 (2)	C13—C12—H12A	120.1
O3—C3—C4	115.4 (2)	C13—C14—H14A	119.8
O4—C7—N1	122.2 (2)	C13—C14—C15	120.4 (2)
O4—C7—C1	120.4 (2)	C14—C15—H15A	120.0
O5—S1—O6	120.54 (12)	C14—C15—C10	120.1 (2)
O5—S1—N2	107.67 (12)	C14—C13—S1	119.8 (2)
O6—S1—N2	104.17 (13)	C14—C13—C12	119.9 (2)
O5—S1—C13	108.68 (12)	C15—C10—N1	123.5 (2)
O6—S1—C13	108.85 (14)	C15—C14—H14A	119.8
O7—C18—C19	116.7 (3)	C16—N3—O7	104.8 (2)
O8—C20—H20A	109.5	C16—C17—H17A	127.6
O8—C20—H20B	109.5	C16—N2—H2B	118.8
O8—C20—H20C	109.5	C16—N2—S1	122.30 (18)
N1—C7—C1	117.3 (2)	C17—C18—C19	133.6 (3)
N2—S1—C13	105.97 (12)	C17—C18—O7	109.7 (3)
N2—C16—C17	129.2 (3)	C18—C19—H19C	109.5
N3—C16—N2	118.5 (2)	C18—C19—H19B	109.5
N3—C16—C17	112.2 (3)	C18—C19—H19A	109.5
C1—C2—H2C	119.9	C18—C17—H17A	127.6
C1—C6—H6A	119.8	C18—C17—C16	104.9 (3)
C2—C3—C4	120.5 (2)	C18—O7—N3	108.4 (2)
C2—C1—C7	118.0 (2)	C20—O8—H8	108 (3)
C2—C1—C6	119.7 (2)	H8A—C8—H8C	109.5
C3—C2—H2C	119.9	H8A—C8—H8B	109.5
C3—C2—C1	120.2 (2)	H8B—C8—H8C	109.5
C3—O3—C9	115.7 (2)	H9A—C9—H9C	109.5
C3—C4—C5	119.1 (2)	H9A—C9—H9B	109.5
C4—O2—H2	110 (2)	H9B—C9—H9C	109.5
C5—C6—H6A	119.8	H19A—C19—H19C	109.5
C5—C6—C1	120.3 (2)	H19A—C19—H19B	109.5
C5—O1—C8	116.1 (2)	H19B—C19—H19C	109.5
C6—C5—C4	120.2 (2)	H20A—C20—H20C	109.5
C6—C1—C7	122.0 (2)	H20A—C20—H20B	109.5
C7—N1—H1A	116.1	H20B—C20—H20C	109.5

S1—C13—C12—C11	175.8 (2)	C1—C6—C5—C4	−0.9 (4)
S1—C13—C14—C15	−175.4 (2)	C1—C6—C5—O1	177.9 (2)
S1—N2—C16—C17	39.3 (4)	C3—C4—C5—C6	0.7 (4)
S1—N2—C16—N3	−144.2 (2)	C3—C4—C5—O1	−178.1 (2)
O2—C4—C3—C2	−178.8 (2)	C3—C2—C1—C7	173.9 (2)
O2—C4—C3—O3	1.2 (4)	C3—C2—C1—C6	−0.6 (4)
O2—C4—C5—C6	179.1 (2)	C5—C4—C3—C2	−0.5 (4)
O2—C4—C5—O1	0.2 (4)	C5—C4—C3—O3	179.5 (2)
O4—C7—C1—C6	151.8 (3)	C5—C6—C1—C7	−173.5 (2)
O4—C7—C1—C2	−22.6 (4)	C5—C6—C1—C2	0.8 (4)
O5—S1—C13—C12	16.6 (3)	C7—N1—C10—C15	−15.7 (4)
O5—S1—C13—C14	−167.0 (2)	C7—N1—C10—C11	165.2 (3)
O5—S1—N2—C16	−42.3 (2)	C8—O1—C5—C4	174.2 (3)
O6—S1—C13—C12	149.6 (2)	C8—O1—C5—C6	−4.6 (4)
O6—S1—C13—C14	−34.0 (3)	C9—O3—C3—C4	−137.6 (3)
O6—S1—N2—C16	−171.4 (2)	C9—O3—C3—C2	42.4 (4)
N1—C10—C11—C12	−178.7 (3)	C10—C11—C12—C13	−1.0 (4)
N1—C10—C15—C14	179.1 (3)	C10—N1—C7—C1	177.2 (2)
N1—C7—C1—C6	−27.2 (4)	C10—N1—C7—O4	−1.8 (4)
N1—C7—C1—C2	158.4 (2)	C11—C10—C15—C14	−1.8 (4)
N2—C16—N3—O7	−177.1 (2)	C12—C13—C14—C15	0.9 (4)
N2—C16—C17—C18	177.1 (3)	C13—C14—C15—C10	0.3 (4)
N2—S1—C13—C12	−98.8 (2)	C13—S1—N2—C16	73.8 (2)
N2—S1—C13—C14	77.5 (2)	C14—C13—C12—C11	−0.6 (4)
N3—O7—C18—C17	0.6 (3)	C15—C10—C11—C12	2.1 (4)
N3—C16—C17—C18	0.4 (3)	C16—C17—C18—C19	177.9 (3)
N3—O7—C18—C19	−178.2 (3)	C16—C17—C18—O7	−0.6 (3)
C1—C2—C3—C4	0.5 (4)	C17—C16—N3—O7	−0.1 (3)
C1—C2—C3—O3	−179.5 (3)	C18—O7—N3—C16	−0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N3ⁱ	0.85 (3)	2.05 (3)	2.852 (4)	157 (3)
O8—H8···O2ⁱⁱ	0.94 (5)	2.12 (6)	3.004 (4)	156 (5)
O8—H8···O1ⁱⁱ	0.94 (5)	2.44 (5)	3.133 (4)	131 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉N₃O₇S·CH₄O
M_r	465.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	12.133 (11), 8.684 (8), 20.983 (19)
β (°)	102.043 (13)
V (Å³)	2162 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.35 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.933, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	11585, 3807, 2900
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.140, 1.05
No. of reflections	3807
No. of parameters	298
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.48

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N3ⁱ	0.85 (3)	2.05 (3)	2.852 (4)	157 (3)
O8—H8···O2ⁱⁱ	0.94 (5)	2.12 (6)	3.004 (4)	156 (5)
O8—H8···O1ⁱⁱ	0.94 (5)	2.44 (5)	3.133 (4)	131 (4)

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

Acknowledgements

This work was supported by grants from the China Postdoctoral Science Foundation (grant No. 2011M500130), the Youth Foundation of Guangxi Botanical Garden of Medicinal Plants project (grant No. guiyaoji 201108) and the National Natural Science Foundation of China (grant nos. 20962002, 20662001).

References

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Volume 68| Part 2| February 2012| Page o379

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

4-Hy­dr­oxy-3,5-dimeth­­oxy-N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamo­yl]phen­yl}benzamide methanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Hydroxy-3,5-dimethoxy-N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}benzamide methanol monosolvate