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

Zia-ur-Rehman, M.; Choudary, J.A.; Elsegood, M.R.J.; Siddiqui, H.L.; Ahmad, S.

doi:10.1107/S1600536807002309

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 63| Part 2| February 2007| Pages o900-o901

https://doi.org/10.1107/S1600536807002309

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

Muhammad Zia-ur-Rehman,^a Jamil Anwar Choudary,^b Mark R. J. Elsegood,^c ^* Hamid Latif Siddiqui ^b and Saeed Ahmad ^d

^aApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan, ^bInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^cChemistry Department, Loughborough University, Loughborough LE11 3TU, England, and ^dDepartment of Chemistry, University of Science and Technology, Bannu, Pakistan
^*Correspondence e-mail: m.r.j.elsegood@lboro.ac.uk

(Received 19 December 2006; accepted 16 January 2007; online 26 January 2007)

In the title compound, C₁₇H₁₅N₃O₅S·C₂H₆OS, the thiazine ring adopts a distorted half-chair conformation. The enolic H atom is involved in both intramolecular and intermolecular O—H⋯O hydrogen bonds, the latter linking the molecules into centrosymmetric pairs. Both anthranilamide H atoms are involved in hydrogen bonding to O atoms of dimethyl sulfoxide molecules, linking the pairs of molecules into chains.

Comment

Owing to their application as non-steroidal anti-inflammatory agents (Turck et al., 1996 ; Bihovsky et al., 2004 ), considerable attention has been given to synthetic and structural investigations of 1,2-benzothiazine 1,1-dioxides and their precursor intermediates (Golič & Leban, 1987 ). During our syntheses of various benzothiazine derivatives (Rehman et al., 2005 ; Rehman et al., 2006 ) the crystal structure of the title compound, (I), has been determined.

In (I) (Fig. 1), the thiazine ring adopts a distorted half-chair conformation. The geometry at N1 is pyramidal, with the methyl group pointing approximately perpendicular to the thiazine ring. Atoms O3 and O1 lie approximately in the plane of the thiazine ring, while atom O2 lies approximately perpendicular to it. Atoms N1, C8, C9, O4 and N2 are coplanar to within 0.093 (2) Å. The S1—N1 bond length of 1.6427 (15) Å is as expected for a sulfonamide.

Like other 1,2-benzothiazine 1,1-dioxide molecules (Golič & Leban, 1987; Fabiola et al., 1998 ), the enolic hydrogen on O3 is involved in intramolecular hydrogen bonding (Table 1), and there is a shortening of the C7—C8 bond [1.362 (3) Å] due to partial double-bond character. Two further intramolecular hydrogen bonds are also present in (I) that are not observed in related benzothiazine molecules such as piroxicam (Kojić-Prodić et al., 1982 ) and meloxicam (Fabiola et al., 1998). Specifically, atom H2 forms hydrogen bonds with both N1 and the anthranilamide atom O5. Atom H3 is also involved in intermolecular hydrogen bonding with atom O4 of an adjacent molecule (Table 1 and Fig. 2), linking the molecules into centrosymmetric pairs.

The O atoms of two symmetry-related dimethyl sulfoxide molecules link adjacent benzothiazine molecules through N—H⋯O hydrogen bonds from H3A and H3B of the benzothiazine amino group (Table 1). These interactions link the centrosymmetric pairs of molecules into chains (Fig. 2).

Figure 1
The molecular structure of (I)

, showing displacement ellipsoids at the 50% probability level for non-H atoms. Dashed lines denote hydrogen bonds.

Figure 2
Projection approximately on to the plane of one hydrogen-bonded chain in (I)

. H atoms not involved in hydrogen bonding have been omitted. Dashed lines denote hydrogen bonds. (Symmetry operators to generate molecules containing O4A and O6A, respectively: 1 − x, 2 − y, 1 − z; −x − 1, 1 − y, 1 − z.)

Experimental

N-[2-(Aminocarbonyl)phenyl]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide was synthesized according to a literature method (Rehman et al., 2006). The compound was dissolved in a mixture of methanol and DMSO (80:20 v/v) at room temperature. Crystals were obtained by slow evaporation and dried under high vacuum.

Crystal data

C₁₇H₁₅N₃O₅S·C₂H₆OS
M_r = 451.51
Triclinic, $[P \overline 1]$
a = 8.4973 (2) Å
b = 10.1959 (4) Å
c = 12.0545 (4) Å
α = 92.132 (2)°
β = 101.540 (2)°
γ = 95.550 (2)°
V = 1016.75 (6) Å³
Z = 2
D_x = 1.475 Mg m⁻³
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 120 (2) K
Plate, colourless
0.54 × 0.42 × 0.11 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.853, T_max = 0.967
20897 measured reflections
4663 independent reflections
3397 reflections with I > 2σ(I)
R_int = 0.049
θ_max = 27.6°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.105
S = 1.04
4663 reflections
286 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0532P)² + 0.2807P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.28 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
O3—H3⋯O4	0.91 (2)	1.75 (2)	2.5771 (18)	150 (2)
O3—H3⋯O4ⁱ	0.91 (2)	2.48 (2)	2.9028 (19)	108.4 (17)
N2—H2⋯O5	0.87 (2)	1.84 (2)	2.583 (2)	142.8 (18)
N2—H2⋯N1	0.87 (2)	2.27 (2)	2.720 (2)	112.0 (16)
N3—H3A⋯O6	0.905 (17)	2.043 (18)	2.911 (2)	160 (2)
N3—H3B⋯O6ⁱⁱ	0.896 (17)	2.064 (18)	2.941 (2)	166 (2)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x-1, -y+1, -z+1.

H atoms bound to C atoms were placed geometrically and refined using a riding model, with C—H = 0.95 Å, U_iso(H) = 1.2 U_eq(C) for aryl H, or C—H = 0.98 Å, U_iso(H) = 1.5 U_eq(C) for methyl H. The methyl groups were allowed to rotate about their local threefold axes. H atoms bound to N and O atoms were located in difference Fourier maps and their coordinates were refined freely with U_iso(H) = 1.2U_eq(N) or 1.5U_eq(O).

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: DENZO; program(s) used to solve structure: SHELXTL (Bruker, 2000 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807002309/bi2133sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807002309/bi2133Isup2.hkl

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

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

Crystal data top

C₁₇H₁₅N₃O₅S·C₂H₆OS	Z = 2
M_r = 451.51	F(000) = 472
Triclinic, P1	D_x = 1.475 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4973 (2) Å	Cell parameters from 4596 reflections
b = 10.1959 (4) Å	θ = 1.0–27.5°
c = 12.0545 (4) Å	µ = 0.31 mm⁻¹
α = 92.132 (2)°	T = 120 K
β = 101.540 (2)°	Lath, colourless
γ = 95.550 (2)°	0.54 × 0.42 × 0.11 mm
V = 1016.75 (6) Å³

Data collection top

Bruker–Nonius KappaCCD diffractometer	4663 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	3397 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
φ and ω scans	θ_max = 27.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→11
T_min = 0.853, T_max = 0.967	k = −13→13
20897 measured 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)] = 0.041	Hydrogen site location: geom except NH & OH coords freely refined
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0532P)² + 0.2807P] where P = (F_o² + 2F_c²)/3
4663 reflections	(Δ/σ)_max = 0.001
286 parameters	Δρ_max = 0.28 e Å⁻³
1 restraint	Δρ_min = −0.48 e Å⁻³

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
N1	0.28059 (17)	0.69118 (16)	0.73479 (12)	0.0181 (3)
S1	0.31964 (5)	0.72519 (5)	0.87245 (4)	0.02156 (14)
O1	0.25883 (16)	0.61339 (15)	0.92530 (11)	0.0299 (4)
O2	0.26700 (16)	0.85129 (15)	0.89310 (11)	0.0273 (3)
C1	0.5321 (2)	0.7427 (2)	0.90615 (15)	0.0201 (4)
C2	0.6158 (2)	0.7076 (2)	1.01020 (16)	0.0249 (4)
H2A	0.5599	0.6651	1.0620	0.030*
C3	0.7825 (2)	0.7359 (2)	1.03684 (16)	0.0275 (5)
H3C	0.8413	0.7143	1.1083	0.033*
C4	0.8639 (2)	0.7955 (2)	0.95985 (17)	0.0275 (5)
H4	0.9780	0.8149	0.9792	0.033*
C5	0.7805 (2)	0.8270 (2)	0.85511 (16)	0.0242 (4)
H5	0.8376	0.8668	0.8027	0.029*
C6	0.6125 (2)	0.80042 (19)	0.82632 (15)	0.0192 (4)
C7	0.5221 (2)	0.83103 (19)	0.71524 (15)	0.0182 (4)
O3	0.60524 (15)	0.91569 (14)	0.65984 (11)	0.0229 (3)
H3	0.538 (3)	0.923 (2)	0.592 (2)	0.034*
C8	0.3662 (2)	0.78096 (19)	0.67303 (15)	0.0176 (4)
C9	0.2777 (2)	0.82173 (19)	0.56403 (15)	0.0182 (4)
O4	0.35180 (15)	0.88358 (14)	0.49923 (11)	0.0229 (3)
N2	0.11631 (18)	0.78914 (16)	0.54384 (13)	0.0182 (3)
H2	0.079 (2)	0.746 (2)	0.5958 (17)	0.022*
C10	−0.0048 (2)	0.82649 (19)	0.45632 (15)	0.0170 (4)
C11	−0.1670 (2)	0.77877 (19)	0.45693 (15)	0.0178 (4)
C12	−0.2889 (2)	0.8181 (2)	0.37254 (16)	0.0218 (4)
H12	−0.3984	0.7879	0.3721	0.026*
C13	−0.2542 (2)	0.8996 (2)	0.28999 (16)	0.0220 (4)
H13	−0.3388	0.9243	0.2331	0.026*
C14	−0.0952 (2)	0.9451 (2)	0.29050 (15)	0.0207 (4)
H14	−0.0711	1.0012	0.2336	0.025*
C15	0.0293 (2)	0.90964 (19)	0.37341 (15)	0.0199 (4)
H15	0.1380	0.9422	0.3735	0.024*
C16	−0.2088 (2)	0.6900 (2)	0.54534 (15)	0.0206 (4)
C17	0.2645 (2)	0.5504 (2)	0.69573 (18)	0.0264 (5)
H17A	0.2273	0.5416	0.6132	0.040*
H17B	0.1860	0.5003	0.7318	0.040*
H17C	0.3695	0.5158	0.7164	0.040*
O5	−0.10788 (16)	0.67029 (16)	0.63157 (11)	0.0305 (4)
N3	−0.35961 (19)	0.63182 (17)	0.53030 (14)	0.0225 (4)
H3A	−0.434 (2)	0.640 (2)	0.4664 (15)	0.027*
H3B	−0.380 (3)	0.573 (2)	0.5803 (16)	0.027*
S2	−0.77356 (5)	0.63477 (5)	0.27891 (4)	0.02196 (14)
O6	−0.60908 (15)	0.59061 (14)	0.32438 (12)	0.0289 (3)
C18	−0.7341 (2)	0.7773 (2)	0.20325 (17)	0.0266 (5)
H18A	−0.6739	0.8483	0.2565	0.040*
H18B	−0.8365	0.8062	0.1645	0.040*
H18C	−0.6701	0.7557	0.1472	0.040*
C19	−0.8603 (2)	0.5220 (2)	0.16109 (16)	0.0265 (5)
H19A	−0.7847	0.5181	0.1097	0.040*
H19B	−0.9612	0.5519	0.1206	0.040*
H19C	−0.8828	0.4341	0.1882	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0168 (8)	0.0205 (9)	0.0170 (8)	−0.0005 (6)	0.0034 (6)	0.0058 (6)
S1	0.0178 (2)	0.0313 (3)	0.0169 (2)	0.0041 (2)	0.00510 (17)	0.0078 (2)
O1	0.0246 (7)	0.0407 (10)	0.0257 (7)	−0.0008 (6)	0.0076 (6)	0.0167 (7)
O2	0.0248 (7)	0.0377 (9)	0.0220 (7)	0.0128 (6)	0.0060 (6)	0.0027 (6)
C1	0.0189 (9)	0.0239 (11)	0.0178 (9)	0.0043 (8)	0.0030 (7)	0.0028 (8)
C2	0.0276 (10)	0.0302 (12)	0.0186 (10)	0.0068 (9)	0.0059 (8)	0.0059 (8)
C3	0.0270 (11)	0.0365 (13)	0.0182 (10)	0.0106 (9)	−0.0011 (8)	0.0019 (9)
C4	0.0197 (10)	0.0349 (13)	0.0254 (10)	0.0030 (9)	−0.0008 (8)	0.0002 (9)
C5	0.0219 (10)	0.0281 (12)	0.0215 (10)	−0.0003 (8)	0.0028 (8)	0.0016 (9)
C6	0.0184 (9)	0.0198 (11)	0.0188 (9)	0.0017 (8)	0.0026 (7)	0.0022 (8)
C7	0.0182 (9)	0.0203 (11)	0.0169 (9)	0.0016 (7)	0.0054 (7)	0.0031 (8)
O3	0.0180 (7)	0.0283 (8)	0.0208 (7)	−0.0041 (6)	0.0017 (5)	0.0083 (6)
C8	0.0166 (9)	0.0198 (11)	0.0173 (9)	0.0000 (7)	0.0055 (7)	0.0045 (7)
C9	0.0167 (9)	0.0202 (11)	0.0174 (9)	0.0006 (7)	0.0037 (7)	0.0005 (8)
O4	0.0176 (7)	0.0315 (9)	0.0195 (7)	−0.0014 (6)	0.0041 (5)	0.0084 (6)
N2	0.0173 (8)	0.0224 (9)	0.0149 (8)	−0.0007 (6)	0.0039 (6)	0.0055 (7)
C10	0.0174 (9)	0.0181 (10)	0.0148 (9)	0.0022 (7)	0.0021 (7)	0.0004 (7)
C11	0.0171 (9)	0.0185 (10)	0.0176 (9)	−0.0001 (7)	0.0039 (7)	0.0017 (7)
C12	0.0164 (9)	0.0256 (12)	0.0224 (10)	0.0011 (8)	0.0022 (7)	0.0023 (8)
C13	0.0205 (9)	0.0239 (11)	0.0201 (9)	0.0040 (8)	−0.0003 (7)	0.0039 (8)
C14	0.0227 (10)	0.0223 (11)	0.0175 (9)	0.0027 (8)	0.0042 (7)	0.0047 (8)
C15	0.0182 (9)	0.0216 (11)	0.0204 (9)	0.0014 (8)	0.0052 (7)	0.0009 (8)
C16	0.0166 (9)	0.0242 (11)	0.0205 (9)	0.0005 (8)	0.0039 (7)	0.0008 (8)
C17	0.0282 (11)	0.0206 (11)	0.0306 (11)	−0.0008 (8)	0.0075 (8)	0.0023 (9)
O5	0.0189 (7)	0.0467 (10)	0.0237 (7)	−0.0035 (6)	−0.0001 (5)	0.0151 (7)
N3	0.0171 (8)	0.0264 (10)	0.0226 (9)	−0.0020 (7)	0.0017 (6)	0.0070 (7)
S2	0.0187 (2)	0.0272 (3)	0.0195 (2)	0.0017 (2)	0.00293 (18)	0.0031 (2)
O6	0.0183 (7)	0.0301 (9)	0.0342 (8)	−0.0006 (6)	−0.0042 (6)	0.0099 (7)
C18	0.0276 (11)	0.0270 (12)	0.0251 (10)	0.0038 (9)	0.0047 (8)	0.0036 (9)
C19	0.0258 (10)	0.0291 (12)	0.0222 (10)	0.0012 (9)	0.0002 (8)	0.0014 (9)

Geometric parameters (Å, º) top

N1—C8	1.435 (2)	C10—C11	1.418 (3)
N1—C17	1.479 (3)	C11—C12	1.399 (2)
N1—S1	1.6427 (15)	C11—C16	1.497 (3)
S1—O1	1.4298 (15)	C12—C13	1.378 (3)
S1—O2	1.4308 (15)	C12—H12	0.950
S1—C1	1.7591 (18)	C13—C14	1.384 (3)
C1—C2	1.390 (3)	C13—H13	0.950
C1—C6	1.402 (3)	C14—C15	1.389 (2)
C2—C3	1.387 (3)	C14—H14	0.950
C2—H2A	0.950	C15—H15	0.950
C3—C4	1.388 (3)	C16—O5	1.244 (2)
C3—H3C	0.950	C16—N3	1.334 (2)
C4—C5	1.384 (3)	C17—H17A	0.980
C4—H4	0.9500	C17—H17B	0.980
C5—C6	1.397 (3)	C17—H17C	0.980
C5—H5	0.950	N3—H3A	0.905 (17)
C6—C7	1.465 (2)	N3—H3B	0.896 (17)
C7—O3	1.343 (2)	S2—O6	1.5133 (13)
C7—C8	1.362 (3)	S2—C19	1.782 (2)
O3—H3	0.91 (2)	S2—C18	1.784 (2)
C8—C9	1.473 (2)	C18—H18A	0.980
C9—O4	1.249 (2)	C18—H18B	0.980
C9—N2	1.350 (2)	C18—H18C	0.980
N2—C10	1.410 (2)	C19—H19A	0.980
N2—H2	0.87 (2)	C19—H19B	0.980
C10—C15	1.390 (3)	C19—H19C	0.980

C8—N1—C17	115.86 (15)	C12—C11—C10	118.03 (17)
C8—N1—S1	114.28 (12)	C12—C11—C16	120.32 (16)
C17—N1—S1	116.99 (12)	C10—C11—C16	121.64 (15)
O1—S1—O2	119.20 (9)	C13—C12—C11	121.63 (17)
O1—S1—N1	108.26 (9)	C13—C12—H12	119.2
O2—S1—N1	108.19 (8)	C11—C12—H12	119.2
O1—S1—C1	109.62 (9)	C12—C13—C14	119.62 (16)
O2—S1—C1	107.77 (9)	C12—C13—H13	120.2
N1—S1—C1	102.52 (8)	C14—C13—H13	120.2
C2—C1—C6	121.65 (17)	C13—C14—C15	120.62 (18)
C2—C1—S1	121.18 (15)	C13—C14—H14	119.7
C6—C1—S1	117.07 (13)	C15—C14—H14	119.7
C3—C2—C1	118.69 (19)	C14—C15—C10	120.03 (17)
C3—C2—H2A	120.7	C14—C15—H15	120.0
C1—C2—H2A	120.7	C10—C15—H15	120.0
C2—C3—C4	120.44 (17)	O5—C16—N3	119.78 (18)
C2—C3—H3C	119.8	O5—C16—C11	122.02 (16)
C4—C3—H3C	119.8	N3—C16—C11	118.20 (16)
C5—C4—C3	120.66 (18)	N1—C17—H17A	109.5
C5—C4—H4	119.7	N1—C17—H17B	109.5
C3—C4—H4	119.7	H17A—C17—H17B	109.5
C4—C5—C6	120.12 (19)	N1—C17—H17C	109.5
C4—C5—H5	119.9	H17A—C17—H17C	109.5
C6—C5—H5	119.9	H17B—C17—H17C	109.5
C5—C6—C1	118.38 (16)	C16—N3—H3A	121.7 (14)
C5—C6—C7	121.02 (17)	C16—N3—H3B	116.8 (14)
C1—C6—C7	120.59 (16)	H3A—N3—H3B	121 (2)
O3—C7—C8	122.88 (16)	O6—S2—C19	104.83 (9)
O3—C7—C6	114.00 (15)	O6—S2—C18	104.89 (9)
C8—C7—C6	123.09 (17)	C19—S2—C18	98.74 (10)
C7—O3—H3	105.3 (15)	S2—C18—H18A	109.5
C7—C8—N1	121.42 (16)	S2—C18—H18B	109.5
C7—C8—C9	120.78 (17)	H18A—C18—H18B	109.5
N1—C8—C9	117.76 (15)	S2—C18—H18C	109.5
O4—C9—N2	124.97 (16)	H18A—C18—H18C	109.5
O4—C9—C8	120.22 (16)	H18B—C18—H18C	109.5
N2—C9—C8	114.80 (16)	S2—C19—H19A	109.5
C9—N2—C10	129.47 (16)	S2—C19—H19B	109.5
C9—N2—H2	116.2 (13)	H19A—C19—H19B	109.5
C10—N2—H2	113.9 (13)	S2—C19—H19C	109.5
C15—C10—N2	122.55 (16)	H19A—C19—H19C	109.5
C15—C10—C11	120.06 (16)	H19B—C19—H19C	109.5
N2—C10—C11	117.37 (16)

C8—N1—S1—O1	−166.38 (12)	O3—C7—C8—C9	−2.2 (3)
C17—N1—S1—O1	−26.32 (15)	C6—C7—C8—C9	176.05 (16)
C8—N1—S1—O2	63.14 (14)	C17—N1—C8—C7	−102.3 (2)
C17—N1—S1—O2	−156.80 (13)	S1—N1—C8—C7	38.2 (2)
C8—N1—S1—C1	−50.56 (14)	C17—N1—C8—C9	80.1 (2)
C17—N1—S1—C1	89.49 (14)	S1—N1—C8—C9	−139.40 (14)
O1—S1—C1—C2	−32.8 (2)	C7—C8—C9—O4	13.0 (3)
O2—S1—C1—C2	98.35 (18)	N1—C8—C9—O4	−169.42 (16)
N1—S1—C1—C2	−147.63 (17)	C7—C8—C9—N2	−165.83 (17)
O1—S1—C1—C6	150.75 (15)	N1—C8—C9—N2	11.8 (2)
O2—S1—C1—C6	−78.09 (17)	O4—C9—N2—C10	−7.4 (3)
N1—S1—C1—C6	35.92 (17)	C8—C9—N2—C10	171.31 (17)
C6—C1—C2—C3	2.8 (3)	C9—N2—C10—C15	−0.7 (3)
S1—C1—C2—C3	−173.53 (16)	C9—N2—C10—C11	−178.94 (18)
C1—C2—C3—C4	−1.4 (3)	C15—C10—C11—C12	−0.1 (3)
C2—C3—C4—C5	−0.4 (3)	N2—C10—C11—C12	178.18 (16)
C3—C4—C5—C6	0.8 (3)	C15—C10—C11—C16	−179.47 (17)
C4—C5—C6—C1	0.5 (3)	N2—C10—C11—C16	−1.2 (3)
C4—C5—C6—C7	−179.02 (18)	C10—C11—C12—C13	0.7 (3)
C2—C1—C6—C5	−2.3 (3)	C16—C11—C12—C13	−179.92 (18)
S1—C1—C6—C5	174.08 (15)	C11—C12—C13—C14	−0.6 (3)
C2—C1—C6—C7	177.22 (18)	C12—C13—C14—C15	−0.1 (3)
S1—C1—C6—C7	−6.4 (3)	C13—C14—C15—C10	0.6 (3)
C5—C6—C7—O3	−17.1 (3)	N2—C10—C15—C14	−178.75 (17)
C1—C6—C7—O3	163.34 (17)	C11—C10—C15—C14	−0.6 (3)
C5—C6—C7—C8	164.54 (19)	C12—C11—C16—O5	−168.09 (19)
C1—C6—C7—C8	−15.0 (3)	C10—C11—C16—O5	11.3 (3)
O3—C7—C8—N1	−179.67 (16)	C12—C11—C16—N3	11.4 (3)
C6—C7—C8—N1	−1.5 (3)	C10—C11—C16—N3	−169.20 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.91 (2)	1.75 (2)	2.5771 (18)	150 (2)
O3—H3···O4ⁱ	0.91 (2)	2.48 (2)	2.9028 (19)	108.4 (17)
N2—H2···O5	0.87 (2)	1.84 (2)	2.583 (2)	142.8 (18)
N2—H2···N1	0.87 (2)	2.27 (2)	2.720 (2)	112.0 (16)
N3—H3A···O6	0.91 (2)	2.04 (2)	2.911 (2)	160 (2)
N3—H3B···O6ⁱⁱ	0.90 (2)	2.06 (2)	2.941 (2)	166 (2)

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

Acknowledgements

The authors acknowledge the EPSRC National Crystallography Service at the University of Southampton for data collection.

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