N-[2-(Amino­carbon­yl)phen­yl]-4-hydr­oxy-2H-1,2-benzothia­zine-3-carboxamide 1,1-dioxide dimethyl sulfoxide solvate

The title compound, C₁₆H₁₃N₃O₅S·C₂H₆OS, is of inter­est as a precursor to biologically active (benzothia­zin-3-yl)quinazolinones and its structure is reported here as the dimethyl sulfoxide (DMSO) solvate. The structure displays intra­molecular N—H...O and O—H...O hydrogen bonding, giving rise to six-membered hydrogen-bonded rings, with head-to-tail inter­molecular pairs of N—H...O hydrogen bonds linking pairs of neighbouring mol­ecules and two independent N—H...O=S inter­molecular hydrogen bonds to the DMSO mol­ecule resulting in the pairs of mol­ecules being linked into stepped chains parallel to a.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.085
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       0.90 mm

Alert level C
PLAT414_ALERT_2_C Short Intra D-H..H-X       H3A    ..  H12     ..       1.99 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Benzothiazines represent an important class of organic heterocyclic compounds characterized by highly pronounced biological properties. 1,2-benzothiazine-1,1-dioxides are known for their anti-rheumatic and anti-inflammatory activities (Turck et al., 1996; Bihovsky et al., 2004) while 1,4-benzothiazine-1,1-dioxides are known for their anti-microbial, anti-allergic and enzyme inhibition activities (Fringuelli et al., 2005). As part of a research program synthesizing benzothiazinic bioactive compounds, N-[2-(aminocarbonyl) phenyl]-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide was prepared from methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide as an intermediate of 2-(4-hydroxy-1,1-dioxido-2H-1,2-benzothiazin-3-yl)quinazolin-4(3H)-ones (Rehman et al., 2005; Rehman et al., 2006).

In this paper, the structure of the title compound, (I), co-crystallized with dimethyl sulfoxide, (C₁₉H₂₁N₃O₆S₂) is reported (Scheme and Fig. 1). The thiazine ring, involving two double bonds, exhibits a half-chair conformation; with S1—C1—C6—C7 relatively planar and N1 showing significant departure from plane due to its pyramidal geometry (sum of angles at N1 = 344.4 °). The torsion angles in the ring also support this conformation (Table 2). The S1—N1—C8 bond angle is the largest [115.33 (9) Å] among those of polymorphs of Piroxicam [113.0 (2) Å; Kojić-Prodić & Ružić-Toroš,1982] or Meloxicam [112.8 (1) Å; Fabiola et al., 1998] due to the absence of the methyl group at N1.

The molecule is not far from being planar since the the enolic hydrogen on O3 is involved in intramolecular hydrogen bonding [O3—H3···O4] with the amido oxygen at C4 giving rise to a six-membered hydrogen bonded ring. Relevant torsion angles are presented in Table 2. The C1—S1 bond (Table 2) is shorter than the normal C—S single bond (1.81–2.55 A) (Weast et al., 1984) due to partial double bond character and is very close to the values observed in hetrocyclic systems [1.57–1.75 (6) Å] described for common sulfonamides (Weast et al., 1984)·The C7—C8 bond length (Table 2) is also shortened due to partial double bond character indicating the stability of the enol form of the molecule.

The intramolecular [N2—H2···O5] interaction forms a second six-membered hydrogen-bonded ring. Each molecule (I) is hydrogen bonded to its neighbour via a centrosymmetric head-to-tail interaction with anthranilamide hydrogen H3B hydrogen bonded to the sulfone oxygen [N3—H3B···O2ⁱⁱ] (Table 1 and Fig. 2). These pairs of molecules are then linked into chains via two independent hydrogen bonds to the DMSO molecule which acts as a bridge; anthranilamide hydrogen, H3A, is linked to DMSO oxygen, O6, which is further bonded to amino hydrogen H1ⁱ of the adjacent benzothiazine molecule to form an infinite stepped chain parallel to a (see Fig. 2 which also gives symmetry operators).

Related literature

For related literature, see: Bihovsky et al. (2004); Fabiola et al. (1998); Fringuelli et al. (2005); Kojić-Prodić & Ružić-Toroš (1982); Rehman et al. (2005, 2006); Turck et al. (1996); Weast et al. (1984).

S2. Experimental

The title compound was synthesized according to our method (Rehman et al., 2005). The compound was co-crystallized with DMSO by dissolving it in a mixture of methanol & DMSO (80:20 v/v) at room temperature and the crystals were obtained by slow evaporation (followed by drying under high vacuum).

S3. Refinement

H atoms bound to C were placed in geometric positions (C—H distance = 0.95 Å for aryl H; 1.00 Å for methyl H) using a riding model. H atoms on N and O had coordinates freely refined. Uĩso~ values were set to 1.2U~eq~ (1.5U~eq~ for methyl H and OH).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000) and local programs.

Figures

	Fig. 1. Asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level, H atoms are represented by circles of arbitrary radius and hydrogen bonds are shown as dashed lines.
	Fig. 2. Packing plot of (I) showing head-to-tail hydrogen bonding between pairs of molecules and hydrogen bonding with dimethyl sulfoxide to form an infinite chains. Symmetry operators: i = x + 1, y, z; ii = -x + 1, -y + 1, -z + 1; iii = x - 1, y, z.

N-[2-(Aminocarbonyl)phenyl]-4-hydroxy-2H-1,2-benzothiazine- 3-carboxamide 1,1-dioxide dimethyl sulfoxide solvate

Crystal data

C16H13N3O5S·C2H6OS	F(000) = 912
Mr = 437.48	Dx = 1.479 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10921 reflections
a = 8.8314 (5) Å	θ = 2.3–28.8°
b = 9.1405 (5) Å	µ = 0.31 mm^−1
c = 24.5041 (14) Å	T = 150 K
β = 96.499 (2)°	Block, colourless
V = 1965.34 (19) Å^3	0.90 × 0.45 × 0.45 mm
Z = 4

Data collection

Bruker SMART 1000 CCD diffractometer	4713 independent reflections
Radiation source: sealed tube	4123 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω rotation with narrow frames scans	θmax = 28.9°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→11
Tmin = 0.766, Tmax = 0.872	k = −12→12
16737 measured reflections	l = −32→32

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: geom except NH & OH coords freely refined
wR(F^2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0437P)^2 + 0.9251P] where P = (Fo^2 + 2Fc^2)/3
4713 reflections	(Δ/σ)max = 0.001
279 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.28875 (13)	0.71759 (13)	0.39205 (4)	0.0229 (2)
H1	0.2612 (19)	0.634 (2)	0.3911 (7)	0.027*
S1	0.23801 (4)	0.80523 (4)	0.444708 (13)	0.02510 (9)
O1	0.33285 (12)	0.93249 (12)	0.45368 (4)	0.0330 (2)
O2	0.23237 (13)	0.70279 (12)	0.48863 (4)	0.0353 (2)
C1	0.05307 (15)	0.86379 (14)	0.42033 (5)	0.0244 (3)
C2	−0.06252 (17)	0.87069 (16)	0.45421 (6)	0.0307 (3)
H2A	−0.0458	0.8371	0.4911	0.037*
C3	−0.20305 (17)	0.92747 (17)	0.43331 (6)	0.0339 (3)
H3C	−0.2837	0.9319	0.4559	0.041*
C4	−0.22597 (17)	0.97760 (17)	0.37973 (7)	0.0339 (3)
H4	−0.3216	1.0189	0.3662	0.041*
C5	−0.11114 (16)	0.96846 (15)	0.34543 (6)	0.0281 (3)
H5	−0.1288	1.0024	0.3086	0.034*
C6	0.03031 (15)	0.90915 (14)	0.36529 (5)	0.0232 (3)
C7	0.14923 (14)	0.88905 (14)	0.32880 (5)	0.0220 (2)
O3	0.13057 (11)	0.96755 (11)	0.28223 (4)	0.0274 (2)
H3	0.209 (2)	0.940 (2)	0.2644 (7)	0.041*
C8	0.26952 (14)	0.79629 (13)	0.34112 (5)	0.0210 (2)
C9	0.38850 (14)	0.78367 (14)	0.30398 (5)	0.0217 (2)
O4	0.37241 (11)	0.84771 (11)	0.25857 (4)	0.0283 (2)
N2	0.51089 (12)	0.70322 (12)	0.32316 (5)	0.0231 (2)
H2	0.5093 (19)	0.6621 (19)	0.3542 (7)	0.028*
C10	0.64929 (14)	0.68352 (14)	0.30069 (5)	0.0218 (2)
C11	0.76511 (14)	0.59886 (14)	0.33032 (5)	0.0216 (2)
C12	0.90429 (15)	0.58378 (14)	0.30863 (5)	0.0240 (3)
H12	0.9827	0.5264	0.3279	0.029*
C13	0.93062 (15)	0.65033 (15)	0.25981 (5)	0.0261 (3)
H13	1.0261	0.6389	0.2459	0.031*
C14	0.81693 (16)	0.73342 (15)	0.23146 (5)	0.0272 (3)
H14	0.8351	0.7801	0.1982	0.033*
C15	0.67642 (16)	0.74937 (15)	0.25111 (5)	0.0264 (3)
H15	0.5985	0.8051	0.2309	0.032*
C16	0.73975 (15)	0.52543 (15)	0.38339 (5)	0.0250 (3)
O5	0.61267 (11)	0.52392 (13)	0.40027 (4)	0.0360 (3)
N3	0.85668 (15)	0.45913 (16)	0.41225 (6)	0.0366 (3)
H3A	0.947 (2)	0.459 (2)	0.4028 (8)	0.044*
H3B	0.840 (2)	0.421 (2)	0.4425 (8)	0.044*
S2	0.23625 (4)	0.28521 (3)	0.414879 (13)	0.02426 (9)
O6	0.17641 (11)	0.43343 (11)	0.39463 (4)	0.0314 (2)
C17	0.35062 (19)	0.22342 (18)	0.36405 (7)	0.0367 (3)
H17A	0.2866	0.2107	0.3290	0.055*
H17B	0.3980	0.1298	0.3755	0.055*
H17C	0.4302	0.2958	0.3596	0.055*
C18	0.38444 (18)	0.31915 (18)	0.46878 (6)	0.0350 (3)
H18A	0.4597	0.3854	0.4556	0.053*
H18B	0.4339	0.2266	0.4805	0.053*
H18C	0.3414	0.3641	0.4999	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0264 (5)	0.0209 (5)	0.0220 (5)	0.0013 (4)	0.0050 (4)	0.0042 (4)
S1	0.02709 (17)	0.02870 (18)	0.01969 (15)	0.00122 (12)	0.00346 (12)	0.00252 (12)
O1	0.0334 (5)	0.0366 (6)	0.0280 (5)	−0.0042 (4)	−0.0001 (4)	−0.0039 (4)
O2	0.0394 (6)	0.0438 (6)	0.0239 (5)	0.0069 (5)	0.0084 (4)	0.0112 (4)
C1	0.0264 (6)	0.0215 (6)	0.0256 (6)	0.0007 (5)	0.0041 (5)	−0.0015 (5)
C2	0.0353 (7)	0.0304 (7)	0.0280 (7)	−0.0008 (6)	0.0099 (6)	−0.0021 (5)
C3	0.0317 (7)	0.0340 (8)	0.0386 (8)	0.0008 (6)	0.0145 (6)	−0.0059 (6)
C4	0.0272 (7)	0.0335 (8)	0.0417 (8)	0.0066 (6)	0.0065 (6)	−0.0041 (6)
C5	0.0268 (7)	0.0267 (7)	0.0310 (7)	0.0044 (5)	0.0041 (5)	−0.0005 (5)
C6	0.0241 (6)	0.0195 (6)	0.0264 (6)	0.0003 (5)	0.0041 (5)	−0.0009 (5)
C7	0.0238 (6)	0.0202 (6)	0.0220 (6)	−0.0015 (5)	0.0020 (5)	0.0017 (4)
O3	0.0279 (5)	0.0291 (5)	0.0256 (5)	0.0051 (4)	0.0044 (4)	0.0081 (4)
C8	0.0227 (6)	0.0211 (6)	0.0196 (6)	−0.0008 (5)	0.0033 (4)	0.0023 (4)
C9	0.0217 (6)	0.0218 (6)	0.0216 (6)	−0.0019 (5)	0.0022 (5)	0.0003 (4)
O4	0.0269 (5)	0.0346 (5)	0.0238 (5)	0.0037 (4)	0.0053 (4)	0.0083 (4)
N2	0.0228 (5)	0.0264 (6)	0.0207 (5)	0.0019 (4)	0.0054 (4)	0.0052 (4)
C10	0.0223 (6)	0.0211 (6)	0.0225 (6)	−0.0011 (5)	0.0044 (5)	−0.0013 (5)
C11	0.0234 (6)	0.0198 (6)	0.0220 (6)	−0.0020 (5)	0.0044 (5)	−0.0002 (4)
C12	0.0236 (6)	0.0220 (6)	0.0268 (6)	0.0002 (5)	0.0042 (5)	−0.0004 (5)
C13	0.0256 (6)	0.0261 (6)	0.0282 (6)	−0.0015 (5)	0.0098 (5)	−0.0025 (5)
C14	0.0321 (7)	0.0271 (6)	0.0239 (6)	−0.0014 (5)	0.0094 (5)	0.0027 (5)
C15	0.0286 (7)	0.0269 (6)	0.0240 (6)	0.0027 (5)	0.0054 (5)	0.0037 (5)
C16	0.0244 (6)	0.0243 (6)	0.0269 (6)	0.0005 (5)	0.0050 (5)	0.0041 (5)
O5	0.0242 (5)	0.0497 (6)	0.0357 (5)	0.0062 (4)	0.0099 (4)	0.0200 (5)
N3	0.0259 (6)	0.0486 (8)	0.0367 (7)	0.0088 (6)	0.0092 (5)	0.0214 (6)
S2	0.02129 (16)	0.02251 (16)	0.02931 (17)	0.00014 (11)	0.00425 (12)	0.00387 (12)
O6	0.0265 (5)	0.0257 (5)	0.0420 (6)	0.0046 (4)	0.0040 (4)	0.0074 (4)
C17	0.0420 (8)	0.0333 (8)	0.0367 (8)	0.0036 (6)	0.0120 (7)	−0.0045 (6)
C18	0.0346 (8)	0.0407 (8)	0.0284 (7)	−0.0038 (6)	−0.0023 (6)	0.0053 (6)

Geometric parameters (Å, º)

N1—C8	1.4337 (16)	C10—C15	1.4004 (18)
N1—S1	1.6244 (11)	C10—C11	1.4157 (18)
N1—H1	0.803 (18)	C11—C12	1.4001 (17)
S1—O2	1.4316 (10)	C11—C16	1.5025 (17)
S1—O1	1.4357 (11)	C12—C13	1.3850 (18)
S1—C1	1.7579 (14)	C12—H12	0.9500
C1—C2	1.3881 (19)	C13—C14	1.382 (2)
C1—C6	1.4035 (18)	C13—H13	0.9500
C2—C3	1.389 (2)	C14—C15	1.3885 (19)
C2—H2A	0.9500	C14—H14	0.9500
C3—C4	1.384 (2)	C15—H15	0.9500
C3—H3C	0.9500	C16—O5	1.2394 (16)
C4—C5	1.391 (2)	C16—N3	1.3298 (18)
C4—H4	0.9500	N3—H3A	0.86 (2)
C5—C6	1.3977 (18)	N3—H3B	0.85 (2)
C5—H5	0.9500	S2—O6	1.5171 (10)
C6—C7	1.4658 (18)	S2—C18	1.7782 (15)
C7—O3	1.3424 (15)	S2—C17	1.7819 (15)
C7—C8	1.3660 (18)	C17—H17A	0.9800
O3—H3	0.90 (2)	C17—H17B	0.9800
C8—C9	1.4705 (17)	C17—H17C	0.9800
C9—O4	1.2511 (15)	C18—H18A	0.9800
C9—N2	1.3472 (17)	C18—H18B	0.9800
N2—C10	1.4078 (16)	C18—H18C	0.9800
N2—H2	0.849 (17)
C8—N1—S1	115.33 (9)	C15—C10—N2	121.71 (12)
C8—N1—H1	116.6 (12)	C15—C10—C11	119.68 (12)
S1—N1—H1	112.5 (12)	N2—C10—C11	118.56 (11)
O2—S1—O1	118.96 (7)	C12—C11—C10	118.26 (11)
O2—S1—N1	108.11 (6)	C12—C11—C16	120.52 (11)
O1—S1—N1	108.21 (6)	C10—C11—C16	121.22 (11)
O2—S1—C1	110.16 (7)	C13—C12—C11	121.68 (12)
O1—S1—C1	107.99 (6)	C13—C12—H12	119.2
N1—S1—C1	102.09 (6)	C11—C12—H12	119.2
C2—C1—C6	121.75 (13)	C14—C13—C12	119.48 (12)
C2—C1—S1	121.90 (11)	C14—C13—H13	120.3
C6—C1—S1	116.29 (10)	C12—C13—H13	120.3
C1—C2—C3	118.92 (13)	C13—C14—C15	120.69 (12)
C1—C2—H2A	120.5	C13—C14—H14	119.7
C3—C2—H2A	120.5	C15—C14—H14	119.7
C4—C3—C2	120.15 (13)	C14—C15—C10	120.20 (12)
C4—C3—H3C	119.9	C14—C15—H15	119.9
C2—C3—H3C	119.9	C10—C15—H15	119.9
C3—C4—C5	121.01 (14)	O5—C16—N3	119.70 (12)
C3—C4—H4	119.5	O5—C16—C11	121.55 (12)
C5—C4—H4	119.5	N3—C16—C11	118.75 (12)
C4—C5—C6	119.79 (13)	C16—N3—H3A	123.4 (13)
C4—C5—H5	120.1	C16—N3—H3B	116.6 (13)
C6—C5—H5	120.1	H3A—N3—H3B	119.8 (18)
C5—C6—C1	118.31 (12)	O6—S2—C18	106.68 (7)
C5—C6—C7	120.66 (12)	O6—S2—C17	104.98 (7)
C1—C6—C7	120.97 (12)	C18—S2—C17	98.44 (8)
O3—C7—C8	122.49 (12)	S2—C17—H17A	109.5
O3—C7—C6	115.09 (11)	S2—C17—H17B	109.5
C8—C7—C6	122.41 (11)	H17A—C17—H17B	109.5
C7—O3—H3	103.6 (12)	S2—C17—H17C	109.5
C7—C8—N1	121.08 (11)	H17A—C17—H17C	109.5
C7—C8—C9	120.29 (11)	H17B—C17—H17C	109.5
N1—C8—C9	118.48 (11)	S2—C18—H18A	109.5
O4—C9—N2	124.86 (12)	S2—C18—H18B	109.5
O4—C9—C8	119.77 (11)	H18A—C18—H18B	109.5
N2—C9—C8	115.35 (11)	S2—C18—H18C	109.5
C9—N2—C10	129.14 (11)	H18A—C18—H18C	109.5
C9—N2—H2	117.4 (11)	H18B—C18—H18C	109.5
C10—N2—H2	113.4 (11)
C8—N1—S1—O2	167.49 (9)	C6—C7—C8—C9	−177.98 (11)
C8—N1—S1—O1	−62.43 (11)	S1—N1—C8—C7	−35.64 (16)
C8—N1—S1—C1	51.33 (11)	S1—N1—C8—C9	139.83 (10)
O2—S1—C1—C2	29.67 (14)	C7—C8—C9—O4	−6.60 (19)
O1—S1—C1—C2	−101.74 (12)	N1—C8—C9—O4	177.89 (12)
N1—S1—C1—C2	144.33 (12)	C7—C8—C9—N2	172.19 (12)
O2—S1—C1—C6	−152.95 (10)	N1—C8—C9—N2	−3.32 (17)
O1—S1—C1—C6	75.65 (11)	O4—C9—N2—C10	6.4 (2)
N1—S1—C1—C6	−38.28 (11)	C8—C9—N2—C10	−172.37 (12)
C6—C1—C2—C3	−1.6 (2)	C9—N2—C10—C15	−1.1 (2)
S1—C1—C2—C3	175.59 (11)	C9—N2—C10—C11	176.67 (12)
C1—C2—C3—C4	−0.7 (2)	C15—C10—C11—C12	−0.07 (18)
C2—C3—C4—C5	1.8 (2)	N2—C10—C11—C12	−177.90 (11)
C3—C4—C5—C6	−0.6 (2)	C15—C10—C11—C16	−179.44 (12)
C4—C5—C6—C1	−1.7 (2)	N2—C10—C11—C16	2.74 (18)
C4—C5—C6—C7	175.70 (13)	C10—C11—C12—C13	0.64 (19)
C2—C1—C6—C5	2.8 (2)	C16—C11—C12—C13	−179.98 (12)
S1—C1—C6—C5	−174.57 (10)	C11—C12—C13—C14	−0.3 (2)
C2—C1—C6—C7	−174.52 (12)	C12—C13—C14—C15	−0.7 (2)
S1—C1—C6—C7	8.09 (17)	C13—C14—C15—C10	1.3 (2)
C5—C6—C7—O3	18.55 (18)	N2—C10—C15—C14	176.87 (13)
C1—C6—C7—O3	−164.17 (12)	C11—C10—C15—C14	−0.9 (2)
C5—C6—C7—C8	−160.94 (13)	C12—C11—C16—O5	−172.01 (13)
C1—C6—C7—C8	16.34 (19)	C10—C11—C16—O5	7.3 (2)
O3—C7—C8—N1	177.95 (11)	C12—C11—C16—N3	7.1 (2)
C6—C7—C8—N1	−2.60 (19)	C10—C11—C16—N3	−173.56 (13)
O3—C7—C8—C9	2.56 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.803 (18)	1.985 (18)	2.7837 (15)	173.5 (17)
O3—H3···O4	0.90 (2)	1.69 (2)	2.5255 (14)	153.7 (17)
N2—H2···O5	0.849 (17)	1.864 (17)	2.5846 (15)	141.8 (16)
N2—H2···N1	0.849 (17)	2.307 (17)	2.7322 (15)	111.3 (13)
N3—H3A···O6^i	0.86 (2)	2.07 (2)	2.9139 (16)	168.3 (18)
N3—H3B···O2^ii	0.85 (2)	2.19 (2)	3.0235 (16)	169.4 (18)

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