4-Hy-droxy-3,5-dimeth-oxy-N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamo-yl]phen-yl}benzamide methanol monosolvate.

The title compound, C(19)H(19)N(3)O(7)S·CH(3)OH, 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 hy-droxy groups from the main mol-ecule and methanol solvent mol-ecules 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 = 465.47

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.140

S = 1.05

3807 reflections

298 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.48 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055991/bh2401sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811055991/bh2401Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H19N3O7S·CH4O	F(000) = 976
Mr = 465.47	Dx = 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

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

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(Fo2) + (0.0122P)2 + 1.2353P] where P = (Fo2 + 2Fc2)/3
3807 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.48 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) .