Salt forms of sulfadiazine with alkali metal and organic cations

The structures of four salt forms of sulfadiazine (SDH) with alkali metal cations are presented. Three contain the deprotonated SD anion (C₁₀H₉N₄O₂S). These are the discrete complex di­aqua­{4-[(pyrimidin-2-yl­aza­nidyl-κN¹)sulfonyl-κO]aniline}lithium(I), [Li(SD)(H₂O)₂], (I), and the coordination polymers poly[{μ₃-4-[(pyrimidin-2-yl­aza­nid­yl)sulfon­yl]aniline}sodium(I)], [Na(SD)]_n, (II), and poly[di­aqua­{μ₃-4-[(pyrimidin-2-yl­aza­nid­yl)sulfon­yl]aniline}potassium(I)], [K(SD)(H₂O)₂]_n, (III). Na complex (II) is a three-dimensional coordination polymer, whilst K complex (III) has two crystallographically independent [K(SD)(H₂O)₂] units per asymmetric unit (Z′ = 2) and gives a two-dimensional coordination polymer whose layers propagate parallel to the crystallographic ab plane. The different bonding modes of the SD anion in these three complexes is discussed. Structure (IV) contains protonated SDH₂ cations {4-[(pyrimidin-2-yl)sul­famo­yl]anilinium, C₁₀H₁₁N₄O₂S} and the Orange G dianion [OG, 7-oxo-8-(phenyl­hydrazinyl­idene)naphthalene-1,3-di­sulfonate, C₁₆H₁₀N₂O₇S₂], namely, 4-[(pyrimi­din-2-yl)sulfamo­yl]anilinium tetra­aqua­[7-oxo-8-(phenyl­hydrazinyl­idene)naph­thalene-1,3-di­sulfonato]­sodium(I) sesquihydrate, (SDH₂)[Na(OG)(H₂O)₄]·1.5H₂O. The [Na(OG)(H₂O)₄]₂ dimers have anti­parallel naphthyl ring structures joined through two Na centres that bond to the hydrazone anions through the O atoms of the ketone and sulfonate substituents. The structures of the salts formed on reaction of SDH with 2-amino­pyridine and ethano­lamine are also presented as 2-amino­pyridinium 4-[(pyrimidin-2-yl­aza­nid­yl)sulfon­yl]aniline, [C₅H₇N₂][SD], (V), and ethano­laminium 4-[(pyrimidin-2-yl­aza­nid­yl)sulfon­yl]aniline monohydrate, [HOCH₂CH₂NH₃][SD]·H₂O, (VI), res­pectively. Structure (V) features a heterodimeric R₂²(8) hydrogen-bond motif between the cation and the anion, whilst structure (VI) has a tetra­meric core of two cations linked by a central R₂²(10) hydrogen-bonded motif which supports two anions linked to this core by R₃³(8) motifs.

Computing details

For all structures, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014). Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for (I), (III); SHELXT (Sheldrick, 2015a) for (II), (V), (VI). For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) for (I), (II), (III), (V), (VI); SHELXT (Sheldrick, 2015a) for (IV).

Diaqua{4-[(pyrimidin-2-ylazanidyl-κN¹)sulfonyl-κO]aniline}lithium(I) (I)

Crystal data

[Li(C10H9N4O2S)(H2O)2]	F(000) = 608
Mr = 292.24	Dx = 1.467 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 11.5095 (4) Å	Cell parameters from 2629 reflections
b = 12.0788 (5) Å	θ = 3.2–29.8°
c = 9.5184 (4) Å	µ = 0.26 mm^−1
β = 91.063 (3)°	T = 123 K
V = 1323.03 (9) Å^3	Block, colourless
Z = 4	0.30 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer	2184 reflections with I > 2σ(I)
Radiation source: tube	Rint = 0.016
ω scans	θmax = 29.0°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −15→13
Tmin = 0.949, Tmax = 1.000	k = −15→15
3390 measured reflections	l = −12→10
2246 independent reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0365P)^2 + 0.3087P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.026	(Δ/σ)max < 0.001
wR(F^2) = 0.066	Δρmax = 0.28 e Å^−3
S = 1.04	Δρmin = −0.25 e Å^−3
2246 reflections	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
207 parameters	Extinction coefficient: 0.0054 (9)
8 restraints	Absolute structure: Refined as an inversion twin.
Hydrogen site location: mixed	Absolute structure parameter: −0.01 (8)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Li1	0.8416 (4)	0.2755 (4)	0.4134 (5)	0.0198 (8)
S1	0.75432 (4)	0.33089 (4)	0.70030 (5)	0.01208 (13)
O1	0.81653 (14)	0.36761 (14)	0.57624 (17)	0.0157 (3)
O2	0.72513 (14)	0.42112 (14)	0.79429 (18)	0.0175 (4)
O1W	0.83115 (15)	0.36603 (15)	0.24923 (19)	0.0211 (4)
O2W	0.97330 (16)	0.19039 (18)	0.3764 (2)	0.0314 (5)
N1	0.63739 (15)	0.26680 (16)	0.6691 (2)	0.0129 (4)
N2	0.71240 (17)	0.16691 (16)	0.4758 (2)	0.0154 (4)
N3	0.52506 (17)	0.13140 (17)	0.5695 (2)	0.0145 (4)
N4	1.05266 (19)	0.00920 (18)	1.0096 (2)	0.0187 (4)
C1	0.62734 (19)	0.18727 (19)	0.5688 (2)	0.0121 (4)
C2	0.6930 (2)	0.0854 (2)	0.3827 (3)	0.0206 (5)
H2	0.7523	0.0684	0.3180	0.025*
C3	0.5921 (2)	0.0254 (2)	0.3763 (3)	0.0231 (5)
H3	0.5798	−0.0317	0.3091	0.028*
C4	0.5093 (2)	0.0531 (2)	0.4735 (3)	0.0184 (5)
H4	0.4376	0.0141	0.4714	0.022*
C5	0.84694 (19)	0.23972 (19)	0.7933 (2)	0.0137 (4)
C6	0.8089 (2)	0.1949 (2)	0.9188 (3)	0.0189 (5)
H6	0.7352	0.2151	0.9541	0.023*
C7	0.8785 (2)	0.1211 (2)	0.9918 (2)	0.0198 (5)
H7	0.8523	0.0904	1.0775	0.024*
C8	0.9871 (2)	0.09088 (19)	0.9410 (2)	0.0161 (5)
C9	1.0257 (2)	0.1391 (2)	0.8169 (2)	0.0157 (5)
H9	1.1005	0.1211	0.7830	0.019*
C10	0.95556 (18)	0.21289 (19)	0.7430 (2)	0.0154 (5)
H10	0.9819	0.2450	0.6582	0.018*
H1W	0.815 (3)	0.4368 (12)	0.251 (4)	0.050 (11)*
H2W	0.890 (2)	0.365 (3)	0.194 (3)	0.055 (12)*
H3W	1.017 (3)	0.202 (3)	0.305 (3)	0.063 (12)*
H4W	1.002 (3)	0.131 (2)	0.413 (4)	0.061 (12)*
H1N	1.122 (3)	0.003 (3)	0.985 (3)	0.025 (8)*
H2N	1.044 (2)	0.012 (2)	1.107 (3)	0.017 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Li1	0.019 (2)	0.019 (2)	0.022 (2)	0.0013 (16)	0.0043 (15)	0.0013 (17)
S1	0.0108 (2)	0.0113 (2)	0.0143 (2)	−0.0013 (2)	0.00227 (16)	−0.0006 (2)
O1	0.0157 (8)	0.0145 (8)	0.0171 (8)	−0.0029 (6)	0.0045 (6)	0.0013 (7)
O2	0.0178 (8)	0.0133 (8)	0.0213 (9)	0.0001 (6)	0.0032 (6)	−0.0042 (7)
O1W	0.0208 (9)	0.0181 (9)	0.0246 (9)	0.0048 (7)	0.0098 (7)	0.0059 (8)
O2W	0.0274 (11)	0.0332 (11)	0.0345 (12)	0.0151 (8)	0.0209 (9)	0.0194 (9)
N1	0.0100 (9)	0.0144 (9)	0.0145 (9)	−0.0011 (7)	0.0020 (6)	−0.0011 (8)
N2	0.0140 (10)	0.0165 (10)	0.0160 (10)	0.0001 (8)	0.0049 (7)	−0.0007 (8)
N3	0.0135 (9)	0.0149 (10)	0.0149 (9)	−0.0035 (8)	0.0013 (7)	0.0015 (8)
N4	0.0194 (11)	0.0187 (11)	0.0180 (11)	0.0018 (8)	−0.0032 (8)	−0.0010 (8)
C1	0.0126 (10)	0.0117 (10)	0.0120 (11)	0.0003 (8)	0.0004 (7)	0.0030 (8)
C2	0.0230 (12)	0.0219 (12)	0.0172 (12)	0.0010 (10)	0.0071 (9)	−0.0048 (10)
C3	0.0262 (13)	0.0218 (12)	0.0214 (13)	−0.0044 (10)	0.0025 (9)	−0.0108 (11)
C4	0.0171 (11)	0.0182 (12)	0.0198 (12)	−0.0042 (9)	−0.0005 (8)	0.0008 (10)
C5	0.0127 (10)	0.0133 (11)	0.0150 (11)	−0.0018 (8)	0.0001 (8)	−0.0019 (9)
C6	0.0157 (11)	0.0212 (12)	0.0200 (13)	−0.0016 (10)	0.0029 (9)	0.0004 (10)
C7	0.0215 (12)	0.0208 (12)	0.0174 (12)	−0.0014 (10)	0.0049 (9)	0.0030 (10)
C8	0.0184 (11)	0.0142 (11)	0.0157 (12)	−0.0026 (9)	−0.0030 (8)	−0.0031 (9)
C9	0.0129 (11)	0.0176 (12)	0.0167 (11)	0.0018 (9)	0.0004 (8)	−0.0036 (9)
C10	0.0139 (11)	0.0177 (12)	0.0145 (11)	−0.0003 (9)	0.0027 (8)	0.0000 (9)

Geometric parameters (Å, º)

Li1—O2W	1.870 (4)	N4—C8	1.396 (3)
Li1—O1W	1.910 (5)	N4—H1N	0.84 (3)
Li1—O1	1.934 (5)	N4—H2N	0.93 (3)
Li1—N2	2.077 (5)	C2—C3	1.370 (4)
Li1—S1	3.002 (4)	C2—H2	0.9500
S1—O2	1.4533 (17)	C3—C4	1.382 (3)
S1—O1	1.4612 (16)	C3—H3	0.9500
S1—N1	1.5761 (19)	C4—H4	0.9500
S1—C5	1.760 (2)	C5—C10	1.385 (3)
O1W—H1W	0.875 (12)	C5—C6	1.390 (3)
O1W—H2W	0.867 (12)	C6—C7	1.378 (3)
O2W—H3W	0.865 (12)	C6—H6	0.9500
O2W—H4W	0.863 (12)	C7—C8	1.398 (3)
N1—C1	1.357 (3)	C7—H7	0.9500
N2—C2	1.340 (3)	C8—C9	1.397 (3)
N2—C1	1.355 (3)	C9—C10	1.386 (3)
N3—C4	1.325 (3)	C9—H9	0.9500
N3—C1	1.357 (3)	C10—H10	0.9500
O2W—Li1—O1W	101.5 (2)	C8—N4—H2N	111.7 (17)
O2W—Li1—O1	126.9 (2)	H1N—N4—H2N	113 (3)
O1W—Li1—O1	108.5 (2)	N2—C1—N3	123.4 (2)
O2W—Li1—N2	107.1 (2)	N2—C1—N1	122.3 (2)
O1W—Li1—N2	124.1 (2)	N3—C1—N1	114.3 (2)
O1—Li1—N2	90.91 (18)	N2—C2—C3	123.3 (2)
O2W—Li1—S1	125.5 (2)	N2—C2—H2	118.4
O1W—Li1—S1	126.84 (19)	C3—C2—H2	118.4
O1—Li1—S1	23.87 (8)	C2—C3—C4	115.9 (2)
N2—Li1—S1	68.13 (13)	C2—C3—H3	122.0
O2—S1—O1	113.09 (10)	C4—C3—H3	122.0
O2—S1—N1	106.15 (10)	N3—C4—C3	123.2 (2)
O1—S1—N1	115.22 (10)	N3—C4—H4	118.4
O2—S1—C5	107.73 (10)	C3—C4—H4	118.4
O1—S1—C5	107.16 (10)	C10—C5—C6	120.4 (2)
N1—S1—C5	107.14 (10)	C10—C5—S1	120.99 (18)
O2—S1—Li1	144.30 (11)	C6—C5—S1	118.58 (18)
O1—S1—Li1	32.38 (11)	C7—C6—C5	119.7 (2)
N1—S1—Li1	91.02 (11)	C7—C6—H6	120.1
C5—S1—Li1	96.20 (11)	C5—C6—H6	120.1
S1—O1—Li1	123.74 (16)	C6—C7—C8	120.7 (2)
Li1—O1W—H1W	124 (2)	C6—C7—H7	119.7
Li1—O1W—H2W	117 (2)	C8—C7—H7	119.7
H1W—O1W—H2W	101 (2)	N4—C8—C9	120.8 (2)
Li1—O2W—H3W	123 (3)	N4—C8—C7	120.1 (2)
Li1—O2W—H4W	134 (3)	C9—C8—C7	119.0 (2)
H3W—O2W—H4W	104 (2)	C10—C9—C8	120.4 (2)
C1—N1—S1	122.79 (16)	C10—C9—H9	119.8
C2—N2—C1	116.9 (2)	C8—C9—H9	119.8
C2—N2—Li1	112.7 (2)	C5—C10—C9	119.7 (2)
C1—N2—Li1	127.0 (2)	C5—C10—H10	120.1
C4—N3—C1	117.3 (2)	C9—C10—H10	120.1
C8—N4—H1N	116 (2)
O2—S1—O1—Li1	−167.45 (18)	C2—C3—C4—N3	−1.0 (4)
N1—S1—O1—Li1	−45.1 (2)	O2—S1—C5—C10	−123.58 (19)
C5—S1—O1—Li1	74.0 (2)	O1—S1—C5—C10	−1.6 (2)
O2—S1—N1—C1	169.98 (18)	N1—S1—C5—C10	122.58 (19)
O1—S1—N1—C1	44.0 (2)	Li1—S1—C5—C10	29.6 (2)
C5—S1—N1—C1	−75.1 (2)	O2—S1—C5—C6	56.4 (2)
Li1—S1—N1—C1	21.7 (2)	O1—S1—C5—C6	178.37 (18)
C2—N2—C1—N3	−1.4 (3)	N1—S1—C5—C6	−57.4 (2)
Li1—N2—C1—N3	156.1 (2)	Li1—S1—C5—C6	−150.4 (2)
C2—N2—C1—N1	179.3 (2)	C10—C5—C6—C7	−1.7 (4)
Li1—N2—C1—N1	−23.3 (4)	S1—C5—C6—C7	178.34 (19)
C4—N3—C1—N2	0.1 (3)	C5—C6—C7—C8	0.1 (4)
C4—N3—C1—N1	179.5 (2)	C6—C7—C8—N4	−174.7 (2)
S1—N1—C1—N2	−8.8 (3)	C6—C7—C8—C9	1.8 (4)
S1—N1—C1—N3	171.78 (16)	N4—C8—C9—C10	174.3 (2)
C1—N2—C2—C3	1.5 (4)	C7—C8—C9—C10	−2.1 (3)
Li1—N2—C2—C3	−159.1 (3)	C6—C5—C10—C9	1.4 (3)
N2—C2—C3—C4	−0.4 (4)	S1—C5—C10—C9	−178.66 (17)
C1—N3—C4—C3	1.2 (4)	C8—C9—C10—C5	0.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2^i	0.88 (1)	2.05 (2)	2.881 (2)	158 (3)
O2W—H3W···N1^ii	0.87 (1)	1.95 (2)	2.805 (3)	170 (4)
O1W—H2W···N3^ii	0.87 (1)	1.97 (1)	2.837 (3)	178 (3)
O2W—H4W···N4^iii	0.86 (1)	2.01 (1)	2.866 (3)	174 (4)
N4—H1N···O2^iv	0.84 (3)	2.40 (3)	3.070 (3)	137 (3)

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

Poly[{µ₃-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (II)

Crystal data

[Na(C10H9N4O2S)]	F(000) = 560
Mr = 272.26	Dx = 1.586 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.9010 (11) Å	Cell parameters from 2254 reflections
b = 10.534 (4) Å	θ = 3.3–29.4°
c = 18.389 (3) Å	µ = 0.32 mm^−1
β = 94.216 (15)°	T = 123 K
V = 1140.0 (5) Å^3	Rod, colourless
Z = 4	0.35 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer	2351 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.029
ω scans	θmax = 29.5°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −7→7
Tmin = 0.961, Tmax = 1.000	k = −12→14
5903 measured reflections	l = −24→24
2786 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0278P)^2 + 0.6871P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2786 reflections	Δρmax = 0.43 e Å^−3
171 parameters	Δρmin = −0.46 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Na1	0.41732 (11)	−0.15699 (7)	0.03430 (4)	0.01483 (18)
S1	0.13569 (7)	0.11080 (4)	0.07836 (2)	0.01030 (12)
O1	0.34050 (19)	0.07207 (12)	0.04443 (7)	0.0130 (3)
O2	0.0133 (2)	0.00644 (12)	0.10838 (7)	0.0152 (3)
N1	−0.0383 (2)	0.18774 (14)	0.02732 (8)	0.0121 (3)
N2	0.2445 (2)	0.32085 (15)	−0.01969 (9)	0.0154 (3)
N3	−0.1495 (2)	0.33011 (16)	−0.06053 (9)	0.0155 (3)
N4	0.4138 (3)	0.41926 (17)	0.34001 (9)	0.0182 (4)
C1	0.0271 (3)	0.28102 (17)	−0.01786 (10)	0.0122 (4)
C2	0.2788 (3)	0.42162 (19)	−0.06182 (11)	0.0197 (4)
H2	0.4295	0.4527	−0.0633	0.024*
C3	0.1082 (3)	0.4826 (2)	−0.10308 (12)	0.0224 (4)
H3	0.1351	0.5566	−0.1307	0.027*
C4	−0.1042 (3)	0.4292 (2)	−0.10165 (11)	0.0198 (4)
H4	−0.2252	0.4653	−0.1318	0.024*
C5	0.2237 (3)	0.20545 (17)	0.15397 (10)	0.0121 (4)
C6	0.0767 (3)	0.21945 (18)	0.20992 (10)	0.0154 (4)
H6	−0.0670	0.1783	0.2059	0.019*
C7	0.1368 (3)	0.29163 (19)	0.27051 (10)	0.0162 (4)
H7	0.0348	0.3008	0.3078	0.019*
C8	0.3482 (3)	0.35145 (18)	0.27712 (10)	0.0141 (4)
C9	0.4953 (3)	0.33673 (19)	0.22135 (11)	0.0177 (4)
H9	0.6399	0.3768	0.2257	0.021*
C10	0.4342 (3)	0.26494 (19)	0.15998 (10)	0.0160 (4)
H10	0.5352	0.2565	0.1224	0.019*
H1N	0.301 (4)	0.454 (2)	0.3602 (13)	0.023 (6)*
H2N	0.528 (4)	0.476 (2)	0.3346 (13)	0.029 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na1	0.0126 (3)	0.0166 (4)	0.0152 (4)	−0.0003 (3)	0.0003 (3)	0.0012 (3)
S1	0.0107 (2)	0.0106 (2)	0.0097 (2)	0.00025 (15)	0.00075 (15)	−0.00029 (17)
O1	0.0130 (6)	0.0136 (6)	0.0126 (6)	0.0030 (5)	0.0020 (5)	−0.0009 (5)
O2	0.0180 (6)	0.0121 (6)	0.0159 (7)	−0.0030 (5)	0.0026 (5)	0.0004 (6)
N1	0.0107 (7)	0.0137 (8)	0.0118 (8)	0.0004 (6)	−0.0005 (5)	0.0013 (6)
N2	0.0119 (7)	0.0156 (8)	0.0188 (8)	−0.0006 (6)	0.0019 (6)	0.0007 (7)
N3	0.0126 (7)	0.0173 (8)	0.0163 (8)	0.0029 (6)	−0.0002 (6)	0.0032 (7)
N4	0.0157 (8)	0.0218 (9)	0.0168 (9)	−0.0016 (7)	−0.0016 (6)	−0.0077 (7)
C1	0.0116 (8)	0.0136 (9)	0.0114 (9)	0.0017 (7)	0.0013 (6)	−0.0022 (7)
C2	0.0165 (9)	0.0183 (10)	0.0247 (11)	−0.0013 (7)	0.0052 (7)	0.0027 (9)
C3	0.0243 (10)	0.0171 (10)	0.0267 (12)	0.0027 (8)	0.0084 (8)	0.0075 (9)
C4	0.0182 (9)	0.0212 (10)	0.0203 (10)	0.0067 (8)	0.0023 (7)	0.0053 (9)
C5	0.0123 (8)	0.0131 (9)	0.0106 (9)	0.0017 (7)	−0.0014 (6)	0.0002 (7)
C6	0.0125 (8)	0.0194 (10)	0.0143 (9)	−0.0019 (7)	0.0011 (7)	−0.0023 (8)
C7	0.0132 (8)	0.0212 (10)	0.0145 (9)	−0.0003 (7)	0.0027 (7)	−0.0021 (8)
C8	0.0146 (8)	0.0143 (9)	0.0129 (9)	0.0013 (7)	−0.0024 (7)	−0.0014 (8)
C9	0.0131 (8)	0.0223 (10)	0.0174 (10)	−0.0041 (7)	−0.0010 (7)	−0.0024 (9)
C10	0.0132 (8)	0.0204 (10)	0.0148 (9)	−0.0012 (7)	0.0031 (7)	−0.0011 (8)

Geometric parameters (Å, º)

Na1—O1^i	2.2897 (15)	N4—C8	1.390 (2)
Na1—N1^ii	2.4533 (15)	N4—Na1^iv	2.5772 (19)
Na1—O1	2.4647 (17)	N4—H1N	0.86 (2)
Na1—N3^ii	2.4836 (18)	N4—H2N	0.91 (2)
Na1—N4^iii	2.5771 (19)	C1—Na1^ii	2.9255 (19)
Na1—N2^i	2.6670 (17)	C2—C3	1.375 (3)
Na1—C1^ii	2.9255 (19)	C2—H2	0.9500
Na1—Na1^i	3.6964 (19)	C3—C4	1.376 (3)
S1—O2	1.4470 (14)	C3—H3	0.9500
S1—O1	1.4585 (13)	C4—H4	0.9500
S1—N1	1.5652 (15)	C5—C10	1.388 (2)
S1—C5	1.7582 (18)	C5—C6	1.402 (2)
O1—Na1^i	2.2897 (15)	C6—C7	1.374 (3)
N1—C1	1.361 (2)	C6—H6	0.9500
N1—Na1^ii	2.4533 (15)	C7—C8	1.395 (2)
N2—C2	1.338 (3)	C7—H7	0.9500
N2—C1	1.353 (2)	C8—C9	1.400 (3)
N2—Na1^i	2.6670 (17)	C9—C10	1.384 (3)
N3—C4	1.328 (3)	C9—H9	0.9500
N3—C1	1.360 (2)	C10—H10	0.9500
N3—Na1^ii	2.4836 (18)
O1^i—Na1—N1^ii	110.47 (5)	C4—N3—C1	116.73 (16)
O1^i—Na1—O1	78.00 (5)	C4—N3—Na1^ii	147.74 (13)
N1^ii—Na1—O1	89.87 (5)	C1—N3—Na1^ii	94.60 (11)
O1^i—Na1—N3^ii	147.71 (6)	C8—N4—Na1^iv	130.68 (13)
N1^ii—Na1—N3^ii	54.64 (5)	C8—N4—H1N	113.5 (15)
O1—Na1—N3^ii	125.52 (6)	Na1^iv—N4—H1N	90.2 (15)
O1^i—Na1—N4^iii	103.13 (6)	C8—N4—H2N	114.1 (15)
N1^ii—Na1—N4^iii	137.28 (6)	Na1^iv—N4—H2N	93.5 (15)
O1—Na1—N4^iii	71.83 (5)	H1N—N4—H2N	112 (2)
N3^ii—Na1—N4^iii	105.32 (6)	N2—C1—N3	123.76 (17)
O1^i—Na1—N2^i	71.51 (5)	N2—C1—N1	123.45 (15)
N1^ii—Na1—N2^i	122.11 (6)	N3—C1—N1	112.79 (15)
O1—Na1—N2^i	141.66 (5)	N2—C1—Na1^ii	168.70 (13)
N3^ii—Na1—N2^i	92.06 (6)	N3—C1—Na1^ii	57.80 (9)
N4^iii—Na1—N2^i	92.82 (6)	N1—C1—Na1^ii	56.52 (8)
O1^i—Na1—C1^ii	134.88 (6)	N2—C2—C3	123.65 (17)
N1^ii—Na1—C1^ii	27.56 (5)	N2—C2—H2	118.2
O1—Na1—C1^ii	106.06 (5)	C3—C2—H2	118.2
N3^ii—Na1—C1^ii	27.60 (5)	C2—C3—C4	115.45 (19)
N4^iii—Na1—C1^ii	121.09 (6)	C2—C3—H3	122.3
N2^i—Na1—C1^ii	111.85 (6)	C4—C3—H3	122.3
O1^i—Na1—Na1^i	40.71 (3)	N3—C4—C3	123.66 (18)
N1^ii—Na1—Na1^i	102.42 (5)	N3—C4—H4	118.2
O1—Na1—Na1^i	37.29 (4)	C3—C4—H4	118.2
N3^ii—Na1—Na1^i	155.65 (5)	C10—C5—C6	119.51 (17)
N4^iii—Na1—Na1^i	86.15 (5)	C10—C5—S1	121.98 (14)
N2^i—Na1—Na1^i	109.06 (5)	C6—C5—S1	118.51 (13)
C1^ii—Na1—Na1^i	128.42 (5)	C7—C6—C5	121.10 (16)
O2—S1—O1	113.78 (8)	C7—C6—H6	119.5
O2—S1—N1	107.35 (8)	C5—C6—H6	119.5
O1—S1—N1	114.59 (8)	C6—C7—C8	119.79 (17)
O2—S1—C5	104.83 (8)	C6—C7—H7	120.1
O1—S1—C5	106.92 (8)	C8—C7—H7	120.1
N1—S1—C5	108.86 (8)	N4—C8—C7	119.84 (17)
S1—O1—Na1^i	137.43 (8)	N4—C8—C9	121.08 (16)
S1—O1—Na1	117.97 (7)	C7—C8—C9	119.01 (17)
Na1^i—O1—Na1	102.00 (5)	C10—C9—C8	121.26 (16)
C1—N1—S1	122.48 (12)	C10—C9—H9	119.4
C1—N1—Na1^ii	95.92 (10)	C8—C9—H9	119.4
S1—N1—Na1^ii	138.08 (9)	C9—C10—C5	119.32 (17)
C2—N2—C1	116.40 (15)	C9—C10—H10	120.3
C2—N2—Na1^i	107.99 (12)	C5—C10—H10	120.3
C1—N2—Na1^i	121.33 (12)
O2—S1—O1—Na1^i	163.45 (10)	Na1^ii—N1—C1—N3	13.88 (16)
N1—S1—O1—Na1^i	39.38 (14)	S1—N1—C1—Na1^ii	162.33 (16)
C5—S1—O1—Na1^i	−81.32 (12)	C1—N2—C2—C3	−1.3 (3)
O2—S1—O1—Na1	5.61 (10)	Na1^i—N2—C2—C3	139.15 (18)
N1—S1—O1—Na1	−118.45 (8)	N2—C2—C3—C4	−3.2 (3)
C5—S1—O1—Na1	120.84 (8)	C1—N3—C4—C3	0.3 (3)
O2—S1—N1—C1	−170.13 (14)	Na1^ii—N3—C4—C3	−164.85 (18)
O1—S1—N1—C1	−42.71 (17)	C2—C3—C4—N3	3.8 (3)
C5—S1—N1—C1	76.92 (16)	O2—S1—C5—C10	141.97 (15)
O2—S1—N1—Na1^ii	−17.00 (15)	O1—S1—C5—C10	20.87 (18)
O1—S1—N1—Na1^ii	110.42 (13)	N1—S1—C5—C10	−103.42 (16)
C5—S1—N1—Na1^ii	−129.95 (13)	O2—S1—C5—C6	−37.32 (16)
C2—N2—C1—N3	5.9 (3)	O1—S1—C5—C6	−158.41 (14)
Na1^i—N2—C1—N3	−128.95 (16)	N1—S1—C5—C6	77.29 (16)
C2—N2—C1—N1	−173.70 (18)	C10—C5—C6—C7	0.3 (3)
Na1^i—N2—C1—N1	51.4 (2)	S1—C5—C6—C7	179.62 (15)
C2—N2—C1—Na1^ii	100.2 (7)	C5—C6—C7—C8	−0.5 (3)
Na1^i—N2—C1—Na1^ii	−34.7 (7)	Na1^iv—N4—C8—C7	81.0 (2)
C4—N3—C1—N2	−5.4 (3)	Na1^iv—N4—C8—C9	−95.8 (2)
Na1^ii—N3—C1—N2	166.65 (16)	C6—C7—C8—N4	−176.79 (18)
C4—N3—C1—N1	174.24 (17)	C6—C7—C8—C9	0.1 (3)
Na1^ii—N3—C1—N1	−13.67 (16)	N4—C8—C9—C10	177.32 (18)
C4—N3—C1—Na1^ii	−172.09 (19)	C7—C8—C9—C10	0.4 (3)
S1—N1—C1—N2	−4.1 (3)	C8—C9—C10—C5	−0.6 (3)
Na1^ii—N1—C1—N2	−166.45 (16)	C6—C5—C10—C9	0.2 (3)
S1—N1—C1—N3	176.20 (13)	S1—C5—C10—C9	−179.03 (15)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N···O2^v	0.86 (2)	2.06 (2)	2.907 (2)	166 (2)
N4—H2N···O1^iv	0.91 (2)	2.52 (2)	2.959 (2)	110.5 (17)

Symmetry codes: (iv) −x+1, y+1/2, −z+1/2; (v) −x, y+1/2, −z+1/2.

Poly[diaqua{µ₃-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}potassium(I)] (III)

Crystal data

[K(C10H9N4O2S)(H2O)2]	Z = 4
Mr = 324.40	F(000) = 672
Triclinic, P1	Dx = 1.594 Mg m^−3
a = 8.8503 (7) Å	Cu Kα radiation, λ = 1.5418 Å
b = 9.6385 (4) Å	Cell parameters from 3605 reflections
c = 15.9734 (7) Å	θ = 4.6–73.6°
α = 92.350 (4)°	µ = 5.09 mm^−1
β = 95.186 (4)°	T = 123 K
γ = 94.209 (4)°	Block, colourless
V = 1351.79 (13) Å^3	0.28 × 0.15 × 0.10 mm

Data collection

Oxford Diffraction Gemini S diffractometer	3951 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.050
ω scans	θmax = 73.8°, θmin = 4.6°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −8→10
Tmin = 0.601, Tmax = 1.000	k = −11→11
15580 measured reflections	l = −19→19
5357 independent reflections

Refinement

Refinement on F^2	14 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.0619P)^2 + 2.5308P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
5357 reflections	Δρmax = 0.81 e Å^−3
404 parameters	Δρmin = −0.45 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
K1	0.24189 (11)	0.55756 (9)	0.47536 (6)	0.0350 (2)
K2	−0.15927 (12)	0.82674 (9)	0.41066 (6)	0.0365 (2)
S1	−0.26644 (12)	0.67031 (10)	0.19910 (6)	0.0304 (2)
S2	−0.05315 (12)	0.81132 (10)	0.61877 (6)	0.0281 (2)
O1	−0.3523 (3)	0.6886 (3)	0.27240 (19)	0.0345 (7)
O2	−0.3075 (4)	0.7607 (3)	0.1321 (2)	0.0398 (7)
O1W	0.4746 (5)	0.4378 (5)	0.5915 (3)	0.0735 (14)
H1W	0.450 (9)	0.398 (6)	0.637 (2)	0.110*
H2W	0.481 (10)	0.362 (4)	0.560 (4)	0.110*
O3	−0.0548 (3)	0.9494 (3)	0.58530 (18)	0.0326 (7)
O2W	0.2375 (5)	0.8119 (4)	0.3937 (2)	0.0549 (10)
H3W	0.196 (7)	0.891 (4)	0.398 (4)	0.082*
H4W	0.199 (7)	0.785 (6)	0.3424 (17)	0.082*
O4	−0.1743 (4)	0.7140 (3)	0.57871 (18)	0.0346 (7)
O3W	−0.0485 (4)	0.5553 (3)	0.39403 (19)	0.0359 (7)
H5W	−0.050 (6)	0.584 (4)	0.3428 (13)	0.054*
H6W	−0.068 (6)	0.4658 (13)	0.384 (3)	0.054*
O4W	−0.4475 (5)	0.8724 (4)	0.4641 (3)	0.0604 (11)
H7W	−0.541 (3)	0.843 (7)	0.445 (4)	0.091*
H8W	−0.466 (9)	0.954 (7)	0.486 (9)	0.091*	0.5
H9W	−0.436 (10)	0.819 (11)	0.507 (5)	0.091*	0.5
N1	−0.0933 (4)	0.6879 (3)	0.2369 (2)	0.0301 (8)
N2	0.1612 (4)	0.7098 (4)	0.2256 (2)	0.0342 (8)
N3	−0.0068 (4)	0.6541 (4)	0.1017 (2)	0.0348 (8)
N4	−0.4201 (6)	0.0807 (5)	0.0779 (3)	0.0504 (12)
N5	0.0982 (4)	0.7389 (4)	0.6097 (2)	0.0317 (8)
N6	0.2546 (4)	0.9310 (3)	0.6755 (2)	0.0303 (8)
N7	0.3546 (5)	0.7193 (4)	0.6308 (2)	0.0384 (9)
N8	−0.1718 (6)	0.8726 (5)	0.9774 (3)	0.0441 (10)
C1	0.0218 (5)	0.6828 (4)	0.1849 (3)	0.0309 (9)
C2	0.2782 (6)	0.7163 (5)	0.1785 (3)	0.0433 (11)
H2	0.3781	0.7352	0.2055	0.052*
C3	0.2599 (6)	0.6967 (5)	0.0925 (3)	0.0447 (12)
H3	0.3436	0.7068	0.0593	0.054*
C4	0.1144 (6)	0.6617 (5)	0.0567 (3)	0.0406 (11)
H4	0.0987	0.6421	−0.0023	0.049*
C5	−0.3070 (5)	0.4959 (4)	0.1601 (3)	0.0299 (9)
C6	−0.2140 (5)	0.3935 (4)	0.1847 (3)	0.0312 (9)
H6	−0.1236	0.4172	0.2207	0.037*
C7	−0.2516 (5)	0.2566 (5)	0.1571 (3)	0.0353 (10)
H7	−0.1851	0.1873	0.1732	0.042*
C8	−0.3841 (5)	0.2186 (5)	0.1065 (3)	0.0377 (11)
C9	−0.4762 (6)	0.3219 (6)	0.0812 (3)	0.0480 (13)
H9	−0.5667	0.2978	0.0453	0.058*
C10	−0.4386 (5)	0.4598 (5)	0.1073 (3)	0.0436 (12)
H10	−0.5028	0.5297	0.0892	0.052*
C11	0.2388 (5)	0.8013 (4)	0.6399 (3)	0.0295 (9)
C12	0.3946 (5)	0.9760 (4)	0.7084 (3)	0.0339 (10)
H12	0.4095	1.0670	0.7344	0.041*
C13	0.5188 (5)	0.8976 (5)	0.7068 (3)	0.0384 (10)
H13	0.6166	0.9299	0.7326	0.046*
C14	0.4908 (6)	0.7693 (5)	0.6650 (3)	0.0428 (11)
H14	0.5740	0.7133	0.6603	0.051*
C15	−0.0866 (5)	0.8295 (4)	0.7260 (2)	0.0269 (8)
C16	−0.1369 (5)	0.7129 (4)	0.7677 (3)	0.0298 (9)
H16	−0.1542	0.6246	0.7382	0.036*
C17	−0.1615 (5)	0.7256 (4)	0.8511 (3)	0.0334 (10)
H17	−0.1935	0.6454	0.8794	0.040*
C18	−0.1399 (5)	0.8561 (4)	0.8955 (3)	0.0313 (9)
C19	−0.0884 (5)	0.9708 (4)	0.8523 (3)	0.0300 (9)
H19	−0.0723	1.0597	0.8810	0.036*
C20	−0.0605 (5)	0.9583 (4)	0.7689 (3)	0.0281 (9)
H20	−0.0236	1.0373	0.7410	0.034*
H1N	−0.515 (8)	0.057 (7)	0.059 (4)	0.07 (2)*
H2N	−0.383 (7)	0.010 (7)	0.111 (4)	0.06 (2)*
H3N	−0.185 (6)	0.800 (5)	1.008 (3)	0.037 (14)*
H4N	−0.156 (6)	0.955 (6)	1.004 (3)	0.053 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.0413 (5)	0.0269 (5)	0.0355 (5)	−0.0036 (4)	0.0044 (4)	−0.0060 (4)
K2	0.0504 (6)	0.0234 (4)	0.0337 (5)	−0.0016 (4)	−0.0020 (4)	−0.0007 (3)
S1	0.0337 (6)	0.0274 (5)	0.0301 (5)	0.0045 (4)	0.0037 (4)	−0.0023 (4)
S2	0.0327 (5)	0.0236 (5)	0.0269 (5)	−0.0012 (4)	0.0021 (4)	−0.0022 (4)
O1	0.0344 (17)	0.0338 (16)	0.0354 (16)	0.0017 (13)	0.0071 (13)	−0.0064 (13)
O2	0.046 (2)	0.0372 (17)	0.0375 (17)	0.0119 (14)	0.0050 (14)	0.0017 (13)
O1W	0.048 (2)	0.079 (3)	0.100 (4)	0.009 (2)	0.018 (2)	0.049 (3)
O3	0.0342 (17)	0.0296 (15)	0.0339 (16)	0.0023 (13)	0.0021 (12)	0.0019 (12)
O2W	0.077 (3)	0.0357 (19)	0.050 (2)	0.0102 (19)	−0.0048 (19)	−0.0027 (16)
O4	0.0381 (17)	0.0325 (16)	0.0310 (15)	−0.0049 (13)	0.0005 (13)	−0.0043 (12)
O3W	0.0464 (19)	0.0274 (15)	0.0330 (16)	0.0014 (14)	0.0028 (14)	−0.0039 (12)
O4W	0.079 (3)	0.039 (2)	0.067 (3)	0.0007 (19)	0.031 (2)	0.0003 (18)
N1	0.036 (2)	0.0247 (17)	0.0286 (18)	−0.0033 (15)	0.0060 (15)	−0.0011 (14)
N2	0.033 (2)	0.0271 (18)	0.043 (2)	0.0030 (15)	0.0090 (16)	0.0011 (15)
N3	0.045 (2)	0.0241 (18)	0.036 (2)	0.0029 (16)	0.0113 (17)	−0.0007 (15)
N4	0.057 (3)	0.045 (3)	0.045 (3)	−0.017 (2)	0.010 (2)	−0.020 (2)
N5	0.040 (2)	0.0240 (17)	0.0315 (19)	0.0023 (15)	0.0070 (15)	−0.0046 (14)
N6	0.033 (2)	0.0240 (17)	0.0340 (19)	−0.0005 (14)	0.0040 (15)	−0.0004 (14)
N7	0.045 (2)	0.034 (2)	0.037 (2)	0.0081 (17)	0.0049 (17)	−0.0048 (16)
N8	0.071 (3)	0.031 (2)	0.031 (2)	−0.002 (2)	0.0101 (19)	−0.0008 (17)
C1	0.038 (2)	0.0164 (19)	0.039 (2)	0.0026 (17)	0.0089 (19)	0.0003 (16)
C2	0.035 (3)	0.033 (2)	0.064 (3)	0.007 (2)	0.012 (2)	0.010 (2)
C3	0.043 (3)	0.041 (3)	0.057 (3)	0.015 (2)	0.023 (2)	0.011 (2)
C4	0.059 (3)	0.029 (2)	0.038 (2)	0.009 (2)	0.017 (2)	0.0040 (18)
C5	0.028 (2)	0.032 (2)	0.029 (2)	0.0021 (17)	0.0035 (16)	−0.0066 (17)
C6	0.032 (2)	0.029 (2)	0.031 (2)	0.0000 (18)	−0.0012 (17)	−0.0006 (17)
C7	0.043 (3)	0.030 (2)	0.033 (2)	0.0007 (19)	0.0027 (19)	−0.0010 (17)
C8	0.037 (3)	0.040 (2)	0.035 (2)	−0.008 (2)	0.0099 (19)	−0.0118 (19)
C9	0.031 (3)	0.060 (3)	0.048 (3)	−0.004 (2)	−0.002 (2)	−0.028 (2)
C10	0.030 (2)	0.054 (3)	0.046 (3)	0.016 (2)	−0.004 (2)	−0.017 (2)
C11	0.035 (2)	0.027 (2)	0.028 (2)	0.0019 (17)	0.0058 (17)	0.0002 (16)
C12	0.036 (2)	0.028 (2)	0.037 (2)	−0.0023 (18)	0.0018 (19)	−0.0017 (17)
C13	0.023 (2)	0.047 (3)	0.044 (3)	0.0054 (19)	−0.0007 (18)	−0.001 (2)
C14	0.036 (3)	0.052 (3)	0.042 (3)	0.018 (2)	0.004 (2)	0.000 (2)
C15	0.028 (2)	0.026 (2)	0.027 (2)	0.0014 (16)	0.0041 (16)	−0.0019 (15)
C16	0.030 (2)	0.022 (2)	0.036 (2)	0.0004 (16)	0.0022 (17)	−0.0044 (16)
C17	0.037 (2)	0.022 (2)	0.041 (2)	−0.0012 (18)	0.0028 (19)	0.0044 (17)
C18	0.030 (2)	0.031 (2)	0.032 (2)	0.0013 (18)	0.0016 (17)	−0.0023 (17)
C19	0.029 (2)	0.023 (2)	0.036 (2)	0.0024 (17)	0.0001 (17)	−0.0061 (16)
C20	0.025 (2)	0.0224 (19)	0.036 (2)	0.0003 (16)	0.0016 (16)	0.0004 (16)

Geometric parameters (Å, º)

K1—O4^i	2.729 (3)	N1—C1	1.373 (5)
K1—O3W	2.771 (3)	N2—C2	1.333 (6)
K1—O1W^ii	2.812 (5)	N2—C1	1.343 (6)
K1—O2W	2.824 (4)	N3—C4	1.343 (6)
K1—N7	2.932 (4)	N3—C1	1.344 (6)
K1—O1W	2.975 (5)	N4—C8	1.393 (6)
K1—O3W^i	3.004 (3)	N4—H1N	0.87 (7)
K1—N5	3.129 (4)	N4—H2N	0.93 (7)
K1—C11	3.457 (4)	N5—C11	1.379 (5)
K1—K2^i	4.2385 (13)	N6—C12	1.336 (6)
K1—K1^i	4.491 (2)	N6—C11	1.344 (5)
K1—K2	4.6167 (15)	N6—K2^iii	2.899 (4)
K1—H6W	3.04 (5)	N7—C14	1.325 (6)
K2—O3^iii	2.759 (3)	N7—C11	1.355 (6)
K2—O4W	2.820 (4)	N8—C18	1.369 (6)
K2—O3W	2.871 (3)	N8—H3N	0.87 (5)
K2—O1	2.883 (3)	N8—H4N	0.88 (6)
K2—N6^iii	2.899 (4)	C2—C3	1.372 (7)
K2—O4	2.947 (3)	C2—H2	0.9500
K2—O3	3.023 (3)	C3—C4	1.373 (7)
K2—N1	3.153 (3)	C3—H3	0.9500
K2—S2	3.3840 (14)	C4—H4	0.9500
K2—C12^iii	3.425 (5)	C5—C6	1.378 (6)
K2—S1	3.6587 (14)	C5—C10	1.388 (6)
K2—K1^i	4.2385 (13)	C6—C7	1.382 (6)
K2—H5W	2.81 (5)	C6—H6	0.9500
K2—H9W	3.01 (11)	C7—C8	1.379 (6)
S1—O2	1.445 (3)	C7—H7	0.9500
S1—O1	1.464 (3)	C8—C9	1.383 (7)
S1—N1	1.589 (4)	C9—C10	1.385 (7)
S1—C5	1.769 (4)	C9—H9	0.9500
S2—O3	1.455 (3)	C10—H10	0.9500
S2—O4	1.455 (3)	C12—C13	1.380 (6)
S2—N5	1.570 (4)	C12—K2^iii	3.425 (5)
S2—C15	1.768 (4)	C12—H12	0.9500
O1W—K1^ii	2.812 (5)	C13—C14	1.376 (7)
O1W—H1W	0.880 (10)	C13—H13	0.9500
O1W—H2W	0.877 (10)	C14—H14	0.9500
O3—K2^iii	2.759 (3)	C15—C20	1.387 (5)
O2W—H3W	0.878 (10)	C15—C16	1.395 (6)
O2W—H4W	0.880 (10)	C16—C17	1.372 (6)
O4—K1^i	2.729 (3)	C16—H16	0.9500
O3W—K1^i	3.004 (3)	C17—C18	1.410 (6)
O3W—H5W	0.874 (10)	C17—H17	0.9500
O3W—H6W	0.873 (10)	C18—C19	1.397 (6)
O4W—H7W	0.878 (10)	C19—C20	1.378 (6)
O4W—H8W	0.879 (10)	C19—H19	0.9500
O4W—H9W	0.878 (10)	C20—H20	0.9500
O4^i—K1—O3W	76.14 (9)	C12^iii—K2—H5W	121.5 (6)
O4^i—K1—O1W^ii	91.40 (13)	S1—K2—H5W	54.1 (7)
O3W—K1—O1W^ii	129.93 (13)	K1^i—K2—H5W	60.3 (5)
O4^i—K1—O2W	133.37 (10)	O3^iii—K2—H9W	124 (2)
O3W—K1—O2W	75.00 (11)	O4W—K2—H9W	17.0 (8)
O1W^ii—K1—O2W	80.19 (13)	O3W—K2—H9W	111.2 (19)
O4^i—K1—N7	138.88 (11)	O1—K2—H9W	87.0 (19)
O3W—K1—N7	125.77 (11)	N6^iii—K2—H9W	91.0 (12)
O1W^ii—K1—N7	95.36 (15)	O4—K2—H9W	55.4 (6)
O2W—K1—N7	87.72 (11)	O3—K2—H9W	73.4 (18)
O4^i—K1—O1W	83.27 (12)	N1—K2—H9W	133 (2)
O3W—K1—O1W	152.02 (11)	S2—K2—H9W	70.2 (11)
O1W^ii—K1—O1W	68.49 (15)	C12^iii—K2—H9W	78.2 (7)
O2W—K1—O1W	132.73 (12)	S1—K2—H9W	109.0 (18)
N7—K1—O1W	62.11 (14)	K1^i—K2—H9W	67.2 (16)
O4^i—K1—O3W^i	76.90 (9)	H5W—K2—H9W	122 (2)
O3W—K1—O3W^i	78.00 (10)	O2—S1—O1	113.35 (19)
O1W^ii—K1—O3W^i	146.61 (12)	O2—S1—N1	115.66 (19)
O2W—K1—O3W^i	130.21 (12)	O1—S1—N1	104.21 (18)
N7—K1—O3W^i	75.36 (10)	O2—S1—C5	108.1 (2)
O1W—K1—O3W^i	79.04 (11)	O1—S1—C5	107.12 (18)
O4^i—K1—N5	130.33 (10)	N1—S1—C5	107.9 (2)
O3W—K1—N5	81.94 (10)	O2—S1—K2	118.44 (13)
O1W^ii—K1—N5	135.34 (13)	O1—S1—K2	47.64 (12)
O2W—K1—N5	80.19 (11)	N1—S1—K2	59.11 (13)
N7—K1—N5	44.19 (10)	C5—S1—K2	132.72 (15)
O1W—K1—N5	97.70 (13)	O3—S2—O4	112.95 (18)
O3W^i—K1—N5	55.02 (9)	O3—S2—N5	114.45 (19)
O4^i—K1—C11	145.79 (10)	O4—S2—N5	105.51 (19)
O3W—K1—C11	103.38 (10)	O3—S2—C15	106.97 (18)
O1W^ii—K1—C11	112.40 (14)	O4—S2—C15	106.49 (18)
O2W—K1—C11	76.90 (10)	N5—S2—C15	110.2 (2)
N7—K1—C11	22.63 (11)	O3—S2—K2	63.26 (12)
O1W—K1—C11	83.25 (13)	O4—S2—K2	60.28 (12)
O3W^i—K1—C11	69.73 (9)	N5—S2—K2	97.00 (14)
N5—K1—C11	23.50 (10)	C15—S2—K2	152.44 (15)
O4^i—K1—K2^i	43.70 (6)	S1—O1—K2	110.33 (15)
O3W—K1—K2^i	94.71 (7)	K1^ii—O1W—K1	111.51 (15)
O1W^ii—K1—K2^i	109.14 (9)	K1^ii—O1W—H1W	126 (5)
O2W—K1—K2^i	169.33 (10)	K1—O1W—H1W	122 (6)
N7—K1—K2^i	96.31 (8)	K1^ii—O1W—H2W	69 (6)
O1W—K1—K2^i	57.39 (8)	K1—O1W—H2W	96 (6)
O3W^i—K1—K2^i	42.59 (6)	H1W—O1W—H2W	98 (2)
N5—K1—K2^i	95.81 (7)	S2—O3—K2^iii	133.47 (17)
C11—K1—K2^i	103.32 (7)	S2—O3—K2	91.28 (13)
O4^i—K1—K1^i	72.58 (7)	K2^iii—O3—K2	114.35 (10)
O3W—K1—K1^i	40.87 (7)	K1—O2W—H3W	139 (4)
O1W^ii—K1—K1^i	162.68 (12)	K1—O2W—H4W	102 (4)
O2W—K1—K1^i	105.79 (10)	H3W—O2W—H4W	99 (2)
N7—K1—K1^i	101.05 (9)	S2—O4—K1^i	143.3 (2)
O1W—K1—K1^i	114.70 (9)	S2—O4—K2	94.33 (14)
O3W^i—K1—K1^i	37.13 (6)	K1^i—O4—K2	96.54 (9)
N5—K1—K1^i	61.97 (7)	K1—O3W—K2	109.81 (10)
C11—K1—K1^i	84.90 (8)	K1—O3W—K1^i	102.00 (10)
K2^i—K1—K1^i	63.78 (3)	K2—O3W—K1^i	92.33 (9)
O4^i—K1—K2	111.87 (7)	K1—O3W—H5W	114 (4)
O3W—K1—K2	35.80 (6)	K2—O3W—H5W	77 (3)
O1W^ii—K1—K2	128.87 (9)	K1^i—O3W—H5W	144 (4)
O2W—K1—K2	50.39 (10)	K1—O3W—H6W	99 (4)
N7—K1—K2	94.90 (8)	K2—O3W—H6W	149 (4)
O1W—K1—K2	154.32 (11)	K1^i—O3W—H6W	71 (3)
O3W^i—K1—K2	84.29 (7)	H5W—O3W—H6W	101 (2)
N5—K1—K2	56.63 (7)	K2—O4W—H7W	134 (5)
C11—K1—K2	72.66 (8)	K2—O4W—H8W	121 (7)
K2^i—K1—K2	119.23 (3)	H7W—O4W—H8W	99 (2)
K1^i—K1—K2	55.45 (3)	K2—O4W—H9W	94 (8)
O4^i—K1—H6W	59.8 (5)	H7W—O4W—H9W	99 (2)
O3W—K1—H6W	16.5 (5)	C1—N1—S1	120.6 (3)
O1W^ii—K1—H6W	127.1 (9)	C1—N1—K2	139.9 (3)
O2W—K1—H6W	89.3 (5)	S1—N1—K2	95.26 (15)
N7—K1—H6W	136.2 (8)	C2—N2—C1	116.9 (4)
O1W—K1—H6W	137.8 (5)	C4—N3—C1	116.1 (4)
O3W^i—K1—H6W	73.6 (8)	C8—N4—H1N	117 (4)
N5—K1—H6W	92.3 (8)	C8—N4—H2N	118 (4)
C11—K1—H6W	115.3 (8)	H1N—N4—H2N	110 (6)
K2^i—K1—H6W	80.9 (6)	C11—N5—S2	122.3 (3)
K1^i—K1—H6W	38.7 (9)	C11—N5—K1	91.7 (2)
K2—K1—H6W	52.1 (5)	S2—N5—K1	138.42 (19)
O3^iii—K2—O4W	118.31 (10)	C12—N6—C11	116.1 (4)
O3^iii—K2—O3W	116.43 (10)	C12—N6—K2^iii	101.5 (3)
O4W—K2—O3W	123.26 (11)	C11—N6—K2^iii	123.5 (3)
O3^iii—K2—O1	130.90 (9)	C14—N7—C11	116.3 (4)
O4W—K2—O1	80.08 (11)	C14—N7—K1	134.6 (3)
O3W—K2—O1	75.53 (9)	C11—N7—K1	101.0 (3)
O3^iii—K2—N6^iii	63.92 (9)	C18—N8—H3N	121 (3)
O4W—K2—N6^iii	74.67 (11)	C18—N8—H4N	120 (4)
O3W—K2—N6^iii	146.26 (10)	H3N—N8—H4N	117 (5)
O1—K2—N6^iii	80.79 (10)	N2—C1—N3	124.9 (4)
O3^iii—K2—O4	111.22 (9)	N2—C1—N1	113.4 (4)
O4W—K2—O4	72.00 (12)	N3—C1—N1	121.7 (4)
O3W—K2—O4	75.72 (9)	N2—C2—C3	122.6 (5)
O1—K2—O4	117.84 (9)	N2—C2—H2	118.7
N6^iii—K2—O4	137.47 (10)	C3—C2—H2	118.7
O3^iii—K2—O3	65.65 (10)	C2—C3—C4	116.6 (4)
O4W—K2—O3	81.82 (11)	C2—C3—H3	121.7
O3W—K2—O3	108.46 (9)	C4—C3—H3	121.7
O1—K2—O3	160.24 (9)	N3—C4—C3	122.8 (5)
N6^iii—K2—O3	101.97 (9)	N3—C4—H4	118.6
O4—K2—O3	47.93 (8)	C3—C4—H4	118.6
O3^iii—K2—N1	97.57 (9)	C6—C5—C10	119.2 (4)
O4W—K2—N1	126.61 (12)	C6—C5—S1	121.0 (3)
O3W—K2—N1	56.72 (9)	C10—C5—S1	119.7 (4)
O1—K2—N1	46.81 (9)	C5—C6—C7	120.2 (4)
N6^iii—K2—N1	89.55 (10)	C5—C6—H6	119.9
O4—K2—N1	131.79 (9)	C7—C6—H6	119.9
O3—K2—N1	151.48 (10)	C8—C7—C6	121.2 (5)
O3^iii—K2—S2	85.85 (7)	C8—C7—H7	119.4
O4W—K2—S2	84.25 (10)	C6—C7—H7	119.4
O3W—K2—S2	85.87 (7)	C7—C8—C9	118.4 (4)
O1—K2—S2	143.14 (7)	C7—C8—N4	120.9 (5)
N6^iii—K2—S2	126.55 (7)	C9—C8—N4	120.7 (5)
O4—K2—S2	25.39 (6)	C8—C9—C10	121.0 (4)
O3—K2—S2	25.46 (6)	C8—C9—H9	119.5
N1—K2—S2	139.86 (8)	C10—C9—H9	119.5
O3^iii—K2—C12^iii	86.35 (10)	C9—C10—C5	119.9 (5)
O4W—K2—C12^iii	61.29 (12)	C9—C10—H10	120.1
O3W—K2—C12^iii	136.33 (10)	C5—C10—H10	120.1
O1—K2—C12^iii	62.11 (10)	N6—C11—N7	124.8 (4)
N6^iii—K2—C12^iii	22.46 (10)	N6—C11—N5	121.6 (4)
O4—K2—C12^iii	132.77 (10)	N7—C11—N5	113.6 (4)
O3—K2—C12^iii	114.98 (9)	N6—C11—K1	154.2 (3)
N1—K2—C12^iii	85.10 (10)	N7—C11—K1	56.4 (2)
S2—K2—C12^iii	135.02 (8)	N5—C11—K1	64.8 (2)
O3^iii—K2—S1	113.47 (7)	N6—C12—C13	123.7 (4)
O4W—K2—S1	101.02 (10)	N6—C12—K2^iii	56.0 (2)
O3W—K2—S1	69.16 (7)	C13—C12—K2^iii	143.9 (3)
O1—K2—S1	22.03 (6)	N6—C12—H12	118.2
N6^iii—K2—S1	79.88 (7)	C13—C12—H12	118.2
O4—K2—S1	131.84 (6)	K2^iii—C12—H12	74.7
O3—K2—S1	176.98 (7)	C14—C13—C12	115.2 (4)
N1—K2—S1	25.63 (7)	C14—C13—H13	122.4
S2—K2—S1	153.19 (4)	C12—C13—H13	122.4
C12^iii—K2—S1	67.56 (8)	N7—C14—C13	123.8 (5)
O3^iii—K2—K1^i	140.99 (7)	N7—C14—H14	118.1
O4W—K2—K1^i	81.88 (9)	C13—C14—H14	118.1
O3W—K2—K1^i	45.08 (7)	C20—C15—C16	120.1 (4)
O1—K2—K1^i	82.84 (7)	C20—C15—S2	120.3 (3)
N6^iii—K2—K1^i	153.33 (8)	C16—C15—S2	119.6 (3)
O4—K2—K1^i	39.76 (6)	C17—C16—C15	120.0 (4)
O3—K2—K1^i	86.84 (6)	C17—C16—H16	120.0
N1—K2—K1^i	94.45 (7)	C15—C16—H16	120.0
S2—K2—K1^i	61.95 (3)	C16—C17—C18	121.0 (4)
C12^iii—K2—K1^i	131.72 (8)	C16—C17—H17	119.5
S1—K2—K1^i	92.52 (3)	C18—C17—H17	119.5
O3^iii—K2—H5W	111.4 (10)	N8—C18—C19	120.3 (4)
O4W—K2—H5W	130.2 (11)	N8—C18—C17	121.9 (4)
O3W—K2—H5W	17.7 (2)	C19—C18—C17	117.7 (4)
O1—K2—H5W	65.1 (9)	C20—C19—C18	121.6 (4)
N6^iii—K2—H5W	128.6 (3)	C20—C19—H19	119.2
O4—K2—H5W	93.3 (2)	C18—C19—H19	119.2
O3—K2—H5W	123.2 (7)	C19—C20—C15	119.5 (4)
N1—K2—H5W	39.1 (3)	C19—C20—H20	120.2
S2—K2—H5W	102.5 (4)	C15—C20—H20	120.2
O2—S1—O1—K2	−107.96 (19)	C10—C5—C6—C7	0.0 (7)
N1—S1—O1—K2	18.6 (2)	S1—C5—C6—C7	176.6 (3)
C5—S1—O1—K2	132.83 (18)	C5—C6—C7—C8	−1.8 (7)
O4—S2—O3—K2^iii	−161.4 (2)	C6—C7—C8—C9	2.5 (7)
N5—S2—O3—K2^iii	−40.7 (3)	C6—C7—C8—N4	179.0 (4)
C15—S2—O3—K2^iii	81.7 (3)	C7—C8—C9—C10	−1.4 (7)
K2—S2—O3—K2^iii	−126.1 (2)	N4—C8—C9—C10	−178.0 (5)
O4—S2—O3—K2	−35.30 (18)	C8—C9—C10—C5	−0.3 (8)
N5—S2—O3—K2	85.46 (17)	C6—C5—C10—C9	1.0 (7)
C15—S2—O3—K2	−152.14 (15)	S1—C5—C10—C9	−175.6 (4)
O3—S2—O4—K1^i	143.5 (3)	C12—N6—C11—N7	−4.4 (6)
N5—S2—O4—K1^i	17.7 (3)	K2^iii—N6—C11—N7	121.7 (4)
C15—S2—O4—K1^i	−99.4 (3)	C12—N6—C11—N5	174.9 (4)
K2—S2—O4—K1^i	107.0 (3)	K2^iii—N6—C11—N5	−59.0 (5)
O3—S2—O4—K2	36.46 (19)	C12—N6—C11—K1	−88.0 (7)
N5—S2—O4—K2	−89.27 (17)	K2^iii—N6—C11—K1	38.2 (8)
C15—S2—O4—K2	153.58 (16)	C14—N7—C11—N6	4.7 (7)
O2—S1—N1—C1	−52.2 (4)	K1—N7—C11—N6	−148.8 (4)
O1—S1—N1—C1	−177.3 (3)	C14—N7—C11—N5	−174.6 (4)
C5—S1—N1—C1	69.1 (3)	K1—N7—C11—N5	32.0 (4)
K2—S1—N1—C1	−161.3 (4)	C14—N7—C11—K1	153.4 (5)
O2—S1—N1—K2	109.16 (17)	S2—N5—C11—N6	−3.2 (6)
O1—S1—N1—K2	−15.96 (17)	K1—N5—C11—N6	151.5 (4)
C5—S1—N1—K2	−129.60 (16)	S2—N5—C11—N7	176.2 (3)
O3—S2—N5—C11	54.6 (4)	K1—N5—C11—N7	−29.2 (4)
O4—S2—N5—C11	179.4 (3)	S2—N5—C11—K1	−154.7 (3)
C15—S2—N5—C11	−66.0 (4)	C11—N6—C12—C13	0.4 (6)
K2—S2—N5—C11	118.3 (3)	K2^iii—N6—C12—C13	−136.1 (4)
O3—S2—N5—K1	−85.3 (3)	C11—N6—C12—K2^iii	136.5 (4)
O4—S2—N5—K1	39.5 (3)	N6—C12—C13—C14	2.8 (7)
C15—S2—N5—K1	154.1 (2)	K2^iii—C12—C13—C14	−74.1 (7)
K2—S2—N5—K1	−21.6 (3)	C11—N7—C14—C13	−1.0 (7)
C2—N2—C1—N3	4.1 (6)	K1—N7—C14—C13	140.9 (4)
C2—N2—C1—N1	−175.5 (4)	C12—C13—C14—N7	−2.5 (7)
C4—N3—C1—N2	−4.1 (6)	O3—S2—C15—C20	−20.6 (4)
C4—N3—C1—N1	175.5 (4)	O4—S2—C15—C20	−141.6 (3)
S1—N1—C1—N2	175.3 (3)	N5—S2—C15—C20	104.4 (4)
K2—N1—C1—N2	25.0 (6)	K2—S2—C15—C20	−85.0 (4)
S1—N1—C1—N3	−4.4 (5)	O3—S2—C15—C16	160.5 (3)
K2—N1—C1—N3	−154.7 (3)	O4—S2—C15—C16	39.5 (4)
C1—N2—C2—C3	0.0 (7)	N5—S2—C15—C16	−74.4 (4)
N2—C2—C3—C4	−3.6 (7)	K2—S2—C15—C16	96.1 (4)
C1—N3—C4—C3	−0.1 (6)	C20—C15—C16—C17	0.4 (6)
C2—C3—C4—N3	3.7 (7)	S2—C15—C16—C17	179.2 (3)
O2—S1—C5—C6	143.5 (4)	C15—C16—C17—C18	1.4 (7)
O1—S1—C5—C6	−94.0 (4)	C16—C17—C18—N8	176.3 (4)
N1—S1—C5—C6	17.7 (4)	C16—C17—C18—C19	−1.8 (7)
K2—S1—C5—C6	−46.4 (4)	N8—C18—C19—C20	−177.7 (4)
O2—S1—C5—C10	−39.9 (4)	C17—C18—C19—C20	0.5 (6)
O1—S1—C5—C10	82.6 (4)	C18—C19—C20—C15	1.3 (6)
N1—S1—C5—C10	−165.7 (4)	C16—C15—C20—C19	−1.7 (6)
K2—S1—C5—C10	130.1 (3)	S2—C15—C20—C19	179.4 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1^i	0.88 (1)	1.93 (2)	2.799 (5)	167 (8)
O1W—H2W···O4W^i	0.88 (1)	2.27 (4)	3.070 (6)	151 (6)
O2W—H3W···O3^iii	0.88 (1)	2.07 (2)	2.933 (5)	167 (6)
O2W—H4W···N2	0.88 (1)	1.97 (2)	2.828 (5)	167 (6)
O3W—H5W···N1	0.87 (1)	2.02 (2)	2.872 (5)	164 (5)
O3W—H6W···N5^i	0.87 (1)	1.98 (1)	2.835 (5)	166 (4)
O4W—H7W···O2W^iv	0.88 (1)	2.05 (2)	2.919 (6)	169 (7)
O4W—H8W···O4W^v	0.88 (1)	2.05 (2)	2.920 (8)	168 (9)
N4—H1N···N4^vi	0.87 (7)	2.50 (6)	3.054 (9)	122 (5)
N4—H2N···O2^vii	0.93 (7)	2.57 (7)	3.431 (7)	153 (5)
N8—H3N···O2^viii	0.87 (5)	2.38 (5)	3.046 (5)	134 (4)
N8—H3N···N3^viii	0.87 (5)	2.61 (5)	3.283 (6)	135 (4)

Symmetry codes: (i) −x, −y+1, −z+1; (iii) −x, −y+2, −z+1; (iv) x−1, y, z; (v) −x−1, −y+2, −z+1; (vi) −x−1, −y, −z; (vii) x, y−1, z; (viii) x, y, z+1.

4-[(Pyrimidin-2-yl)sulfamoyl]anilinium tetraaqua[7-oxo-8-(phenylhydrazinylidene)naphthalene-1,3-disulfonato]sodium(I) sesquihydrate (IV)

Crystal data

(C10H11N4O2S)[Na(C16H10N2O7S2)(H2O)4]·1.5H2O	F(000) = 1620
Mr = 779.74	Dx = 1.599 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.7688 (1) Å	Cell parameters from 35404 reflections
b = 16.9040 (1) Å	θ = 3.6–70.3°
c = 15.7411 (1) Å	µ = 2.95 mm^−1
β = 107.609 (1)°	T = 100 K
V = 3238.42 (4) Å^3	Block, red
Z = 4	0.12 × 0.08 × 0.04 mm

Data collection

XtaLAB AFC11 (RCD3) diffractometer	5686 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.027
ω scans	θmax = 68.3°, θmin = 3.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017)	h = −15→15
Tmin = 0.615, Tmax = 1.000	k = −20→20
59125 measured reflections	l = −18→17
5913 independent reflections

Refinement

Refinement on F^2	13 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.075	w = 1/[σ^2(Fo^2) + (0.0364P)^2 + 2.347P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
5913 reflections	Δρmax = 0.26 e Å^−3
537 parameters	Δρmin = −0.39 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Na1	−0.36434 (5)	0.35305 (4)	0.00412 (4)	0.02103 (14)
S1	0.25698 (3)	0.53159 (2)	0.56811 (2)	0.01894 (9)
S2	0.28977 (3)	0.35439 (2)	0.12953 (2)	0.01723 (9)
S3	0.34948 (3)	0.66079 (2)	0.22267 (2)	0.01823 (9)
O1	0.30756 (9)	0.60882 (7)	0.58033 (7)	0.0231 (2)
O2	0.25734 (9)	0.48924 (7)	0.64777 (7)	0.0232 (2)
O1W	−0.35372 (9)	0.22020 (7)	0.04238 (8)	0.0218 (2)
O3	−0.16759 (8)	0.36126 (6)	0.04200 (7)	0.0209 (2)
O2W	−0.39276 (13)	0.36471 (9)	0.15242 (9)	0.0366 (3)
O4	0.23184 (9)	0.28982 (6)	0.15504 (8)	0.0242 (2)
O3W	−0.56243 (11)	0.33362 (8)	−0.06717 (10)	0.0324 (3)
O5	0.29466 (9)	0.35183 (7)	0.03839 (7)	0.0247 (3)
O4W	−0.40375 (13)	0.48626 (9)	−0.02427 (12)	0.0467 (4)
H7W	−0.3673 (17)	0.5308 (9)	−0.0208 (17)	0.056*
H8W	−0.449 (3)	0.501 (2)	0.006 (3)	0.056*	0.5
H14W	−0.463 (2)	0.499 (2)	−0.068 (2)	0.056*	0.5
O5W	−0.6489 (2)	0.33037 (15)	−0.24880 (18)	0.0323 (5)	0.5
H9W	−0.677 (3)	0.2873 (16)	−0.279 (2)	0.039*	0.5
H10W	−0.590 (2)	0.336 (2)	−0.267 (3)	0.039*	0.5
O6W	−0.3558 (3)	0.52405 (18)	0.16139 (18)	0.0459 (8)	0.5
H11W	−0.366 (2)	0.5317 (15)	0.2141 (10)	0.055*
H12W	−0.367 (4)	0.4725 (8)	0.160 (3)	0.055*	0.5
O7W	−0.4311 (2)	0.54771 (18)	0.19266 (18)	0.0392 (7)	0.5
H13W	−0.451 (3)	0.566 (3)	0.2374 (18)	0.047*	0.5
O6	0.40067 (8)	0.36455 (6)	0.19268 (7)	0.0200 (2)
O7	0.36235 (9)	0.69334 (7)	0.14107 (7)	0.0228 (2)
O8	0.44918 (9)	0.62573 (7)	0.28078 (8)	0.0297 (3)
O9	0.29864 (9)	0.71689 (7)	0.26880 (7)	0.0241 (2)
N1	0.13018 (10)	0.53245 (8)	0.50886 (8)	0.0193 (3)
N2	0.14382 (11)	0.63967 (8)	0.41387 (9)	0.0205 (3)
N3	−0.02496 (10)	0.58329 (8)	0.41174 (9)	0.0202 (3)
N4	0.47872 (12)	0.31848 (9)	0.37342 (10)	0.0228 (3)
N5	0.04786 (10)	0.34343 (7)	0.02685 (8)	0.0165 (3)
N6	−0.02618 (10)	0.29254 (7)	−0.01560 (8)	0.0173 (3)
C1	0.08718 (12)	0.58593 (9)	0.44525 (10)	0.0185 (3)
C2	0.08701 (13)	0.69124 (10)	0.35332 (10)	0.0216 (3)
H2	0.1270	0.7293	0.3313	0.026*
C3	−0.02726 (13)	0.69278 (10)	0.32031 (11)	0.0232 (3)
H3	−0.0650	0.7314	0.2784	0.028*
C4	−0.08209 (13)	0.63587 (10)	0.35134 (11)	0.0238 (3)
H4	−0.1600	0.6334	0.3304	0.029*
C5	0.32606 (12)	0.47095 (9)	0.51081 (10)	0.0197 (3)
C6	0.35300 (12)	0.49962 (10)	0.43696 (10)	0.0223 (3)
H6	0.3365	0.5527	0.4176	0.027*
C7	0.40425 (12)	0.44943 (10)	0.39231 (10)	0.0219 (3)
H7	0.4236	0.4677	0.3420	0.026*
C8	0.42703 (12)	0.37216 (10)	0.42193 (10)	0.0205 (3)
C9	0.40333 (13)	0.34437 (10)	0.49661 (11)	0.0221 (3)
H9	0.4223	0.2919	0.5171	0.027*
C10	0.35154 (12)	0.39416 (10)	0.54122 (10)	0.0218 (3)
H10	0.3336	0.3759	0.5922	0.026*
C11	0.01948 (12)	0.40012 (9)	0.07444 (10)	0.0159 (3)
C12	−0.09441 (12)	0.41261 (9)	0.07379 (9)	0.0175 (3)
C13	−0.12211 (12)	0.48735 (9)	0.10541 (10)	0.0198 (3)
H13	−0.1955	0.4971	0.1051	0.024*
C14	−0.04523 (12)	0.54336 (9)	0.13538 (10)	0.0188 (3)
H14	−0.0671	0.5934	0.1516	0.023*
C15	0.06970 (12)	0.53059 (9)	0.14404 (10)	0.0166 (3)
C16	0.10495 (12)	0.45694 (9)	0.11881 (9)	0.0157 (3)
C17	0.22061 (12)	0.44559 (9)	0.13890 (10)	0.0168 (3)
C18	0.29200 (12)	0.50782 (9)	0.17202 (10)	0.0186 (3)
H18	0.3687	0.4999	0.1835	0.022*
C19	0.25427 (12)	0.58168 (9)	0.18898 (10)	0.0178 (3)
C20	0.14397 (12)	0.59221 (9)	0.17777 (10)	0.0178 (3)
H20	0.1182	0.6413	0.1929	0.021*
C21	−0.00296 (12)	0.23542 (9)	−0.07255 (10)	0.0178 (3)
C22	−0.09205 (13)	0.19251 (9)	−0.12561 (10)	0.0204 (3)
H22	−0.1643	0.2031	−0.1234	0.024*
C23	−0.07414 (14)	0.13423 (10)	−0.18169 (11)	0.0237 (3)
H23	−0.1343	0.1047	−0.2182	0.028*
C24	0.03150 (14)	0.11899 (10)	−0.18464 (11)	0.0243 (3)
H24	0.0438	0.0786	−0.2225	0.029*
C25	0.11952 (14)	0.16297 (10)	−0.13190 (11)	0.0242 (3)
H25	0.1916	0.1526	−0.1346	0.029*
C26	0.10358 (13)	0.22174 (10)	−0.07551 (10)	0.0211 (3)
H26	0.1637	0.2519	−0.0398	0.025*
H1W	−0.349 (2)	0.2133 (14)	0.0986 (18)	0.049 (7)*
H2W	−0.299 (2)	0.1888 (15)	0.0354 (16)	0.052 (7)*
H3W	−0.360 (2)	0.3264 (17)	0.1861 (18)	0.057 (8)*
H4W	−0.461 (3)	0.3655 (19)	0.161 (2)	0.089 (11)*
H5W	−0.607 (2)	0.3395 (16)	−0.0361 (19)	0.061 (8)*
H6W	−0.591 (3)	0.365 (2)	−0.109 (2)	0.086 (11)*
H1N	−0.0943 (19)	0.2989 (13)	−0.0086 (14)	0.039 (6)*
H2N	0.4668 (19)	0.2671 (15)	0.3875 (16)	0.046 (6)*
H3N	0.4510 (18)	0.3275 (13)	0.3137 (16)	0.036 (6)*
H4N	0.552 (2)	0.3289 (13)	0.3887 (14)	0.036 (6)*
H5N	−0.0568 (18)	0.5484 (13)	0.4332 (14)	0.034 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na1	0.0167 (3)	0.0247 (3)	0.0222 (3)	0.0009 (2)	0.0066 (2)	0.0023 (2)
S1	0.01371 (18)	0.0258 (2)	0.01688 (18)	0.00205 (14)	0.00401 (14)	0.00107 (14)
S2	0.01208 (17)	0.02132 (19)	0.01829 (19)	0.00029 (13)	0.00458 (14)	0.00044 (14)
S3	0.01672 (18)	0.02092 (19)	0.01605 (18)	−0.00479 (14)	0.00343 (14)	−0.00034 (14)
O1	0.0168 (5)	0.0278 (6)	0.0235 (6)	−0.0008 (4)	0.0044 (4)	−0.0022 (5)
O2	0.0188 (5)	0.0335 (6)	0.0174 (5)	0.0043 (5)	0.0054 (4)	0.0033 (5)
O1W	0.0204 (6)	0.0252 (6)	0.0199 (6)	0.0006 (5)	0.0061 (4)	0.0006 (5)
O3	0.0146 (5)	0.0233 (6)	0.0249 (6)	−0.0033 (4)	0.0061 (4)	−0.0030 (4)
O2W	0.0409 (8)	0.0400 (8)	0.0350 (7)	0.0161 (6)	0.0208 (6)	0.0089 (6)
O4	0.0180 (5)	0.0200 (5)	0.0352 (6)	−0.0002 (4)	0.0090 (5)	0.0039 (5)
O3W	0.0246 (6)	0.0369 (7)	0.0407 (8)	0.0063 (5)	0.0171 (6)	0.0062 (6)
O5	0.0170 (5)	0.0378 (7)	0.0201 (6)	0.0016 (5)	0.0069 (4)	−0.0037 (5)
O4W	0.0522 (9)	0.0349 (7)	0.0683 (11)	0.0142 (7)	0.0413 (8)	0.0217 (7)
O5W	0.0279 (13)	0.0334 (14)	0.0360 (14)	−0.0018 (10)	0.0103 (11)	−0.0034 (11)
O6W	0.070 (2)	0.0441 (16)	0.0218 (13)	0.0273 (15)	0.0117 (13)	0.0043 (12)
O7W	0.0281 (14)	0.0483 (17)	0.0362 (15)	0.0008 (12)	0.0021 (11)	0.0159 (13)
O6	0.0129 (5)	0.0250 (6)	0.0204 (5)	0.0012 (4)	0.0026 (4)	0.0015 (4)
O7	0.0257 (6)	0.0247 (6)	0.0198 (6)	−0.0074 (5)	0.0098 (5)	−0.0014 (4)
O8	0.0205 (6)	0.0305 (6)	0.0299 (6)	−0.0045 (5)	−0.0047 (5)	0.0029 (5)
O9	0.0250 (6)	0.0269 (6)	0.0223 (6)	−0.0072 (5)	0.0101 (5)	−0.0067 (5)
N1	0.0130 (6)	0.0250 (7)	0.0192 (6)	0.0018 (5)	0.0039 (5)	0.0018 (5)
N2	0.0174 (6)	0.0246 (7)	0.0192 (6)	0.0006 (5)	0.0050 (5)	0.0011 (5)
N3	0.0142 (6)	0.0266 (7)	0.0201 (7)	0.0013 (5)	0.0058 (5)	0.0025 (5)
N4	0.0166 (7)	0.0317 (8)	0.0209 (7)	0.0058 (6)	0.0066 (6)	0.0019 (6)
N5	0.0158 (6)	0.0176 (6)	0.0149 (6)	−0.0007 (5)	0.0028 (5)	0.0023 (5)
N6	0.0139 (6)	0.0202 (6)	0.0172 (6)	−0.0010 (5)	0.0038 (5)	−0.0005 (5)
C1	0.0158 (7)	0.0226 (8)	0.0173 (7)	0.0023 (6)	0.0053 (6)	−0.0031 (6)
C2	0.0233 (8)	0.0234 (8)	0.0191 (8)	0.0006 (6)	0.0078 (6)	−0.0010 (6)
C3	0.0225 (8)	0.0274 (8)	0.0193 (8)	0.0058 (7)	0.0057 (6)	0.0030 (6)
C4	0.0168 (8)	0.0331 (9)	0.0202 (8)	0.0056 (6)	0.0040 (6)	0.0021 (7)
C5	0.0114 (7)	0.0282 (8)	0.0183 (7)	0.0010 (6)	0.0028 (6)	0.0003 (6)
C6	0.0180 (7)	0.0275 (8)	0.0202 (8)	0.0030 (6)	0.0042 (6)	0.0036 (6)
C7	0.0163 (7)	0.0316 (9)	0.0177 (7)	0.0027 (6)	0.0050 (6)	0.0039 (6)
C8	0.0115 (7)	0.0304 (9)	0.0186 (8)	0.0032 (6)	0.0032 (6)	0.0002 (6)
C9	0.0174 (7)	0.0271 (8)	0.0214 (8)	0.0041 (6)	0.0052 (6)	0.0039 (6)
C10	0.0159 (7)	0.0304 (9)	0.0190 (8)	0.0014 (6)	0.0050 (6)	0.0035 (6)
C11	0.0144 (7)	0.0181 (7)	0.0145 (7)	0.0001 (6)	0.0036 (5)	0.0024 (6)
C12	0.0155 (7)	0.0224 (8)	0.0140 (7)	−0.0009 (6)	0.0035 (6)	0.0024 (6)
C13	0.0150 (7)	0.0251 (8)	0.0203 (8)	0.0015 (6)	0.0069 (6)	0.0004 (6)
C14	0.0189 (7)	0.0205 (8)	0.0179 (7)	0.0021 (6)	0.0067 (6)	0.0009 (6)
C15	0.0165 (7)	0.0205 (7)	0.0125 (7)	−0.0002 (6)	0.0041 (6)	0.0030 (6)
C16	0.0153 (7)	0.0202 (7)	0.0117 (7)	−0.0006 (6)	0.0045 (6)	0.0033 (6)
C17	0.0157 (7)	0.0207 (7)	0.0141 (7)	−0.0002 (6)	0.0048 (6)	0.0026 (6)
C18	0.0148 (7)	0.0240 (8)	0.0161 (7)	−0.0016 (6)	0.0034 (6)	0.0037 (6)
C19	0.0175 (7)	0.0212 (7)	0.0131 (7)	−0.0032 (6)	0.0024 (6)	0.0029 (6)
C20	0.0199 (7)	0.0189 (7)	0.0147 (7)	−0.0010 (6)	0.0051 (6)	0.0014 (6)
C21	0.0201 (7)	0.0175 (7)	0.0155 (7)	0.0010 (6)	0.0049 (6)	0.0021 (6)
C22	0.0189 (7)	0.0225 (8)	0.0196 (8)	−0.0017 (6)	0.0055 (6)	0.0016 (6)
C23	0.0256 (8)	0.0234 (8)	0.0209 (8)	−0.0058 (6)	0.0051 (7)	−0.0024 (6)
C24	0.0312 (9)	0.0229 (8)	0.0187 (8)	0.0022 (7)	0.0077 (7)	−0.0019 (6)
C25	0.0208 (8)	0.0294 (9)	0.0225 (8)	0.0046 (7)	0.0065 (6)	−0.0006 (7)
C26	0.0179 (7)	0.0247 (8)	0.0193 (8)	0.0003 (6)	0.0034 (6)	−0.0009 (6)

Geometric parameters (Å, º)

Na1—O1W	2.3184 (13)	N5—C11	1.3322 (19)
Na1—O4W	2.3211 (15)	N6—C21	1.409 (2)
Na1—O3	2.4042 (12)	N6—H1N	0.92 (2)
Na1—O7^i	2.4237 (12)	C2—C3	1.393 (2)
Na1—O3W	2.4592 (14)	C2—H2	0.9500
Na1—O2W	2.4764 (14)	C3—C4	1.364 (2)
S1—O2	1.4428 (11)	C3—H3	0.9500
S1—O1	1.4433 (12)	C4—H4	0.9500
S1—N1	1.6055 (13)	C5—C10	1.388 (2)
S1—C5	1.7674 (16)	C5—C6	1.395 (2)
S2—O4	1.4419 (11)	C6—C7	1.386 (2)
S2—O5	1.4554 (12)	C6—H6	0.9500
S2—O6	1.4735 (11)	C7—C8	1.388 (2)
S2—C17	1.8048 (15)	C7—H7	0.9500
S3—O8	1.4506 (12)	C8—C9	1.382 (2)
S3—O7	1.4516 (11)	C9—C10	1.385 (2)
S3—O9	1.4605 (12)	C9—H9	0.9500
S3—C19	1.7769 (15)	C10—H10	0.9500
O1W—H1W	0.88 (3)	C11—C16	1.463 (2)
O1W—H2W	0.91 (3)	C11—C12	1.467 (2)
O3—C12	1.2626 (18)	C12—C13	1.441 (2)
O2W—H3W	0.86 (3)	C13—C14	1.343 (2)
O2W—H4W	0.92 (4)	C13—H13	0.9500
O3W—H5W	0.86 (3)	C14—C15	1.448 (2)
O3W—H6W	0.83 (4)	C14—H14	0.9500
O4W—H7W	0.879 (10)	C15—C20	1.401 (2)
O4W—H8W	0.883 (10)	C15—C16	1.421 (2)
O4W—H14W	0.886 (10)	C16—C17	1.427 (2)
O5W—H9W	0.883 (10)	C17—C18	1.386 (2)
O5W—H10W	0.885 (10)	C18—C19	1.393 (2)
O6W—H11W	0.886 (10)	C18—H18	0.9500
O6W—H12W	0.881 (10)	C19—C20	1.377 (2)
O7W—H13W	0.875 (10)	C20—H20	0.9500
O7—Na1^i	2.4237 (12)	C21—C22	1.394 (2)
N1—C1	1.337 (2)	C21—C26	1.395 (2)
N2—C2	1.333 (2)	C22—C23	1.387 (2)
N2—C1	1.345 (2)	C22—H22	0.9500
N3—C4	1.344 (2)	C23—C24	1.388 (2)
N3—C1	1.369 (2)	C23—H23	0.9500
N3—H5N	0.84 (2)	C24—C25	1.393 (2)
N4—C8	1.465 (2)	C24—H24	0.9500
N4—H2N	0.92 (3)	C25—C26	1.388 (2)
N4—H3N	0.91 (2)	C25—H25	0.9500
N4—H4N	0.91 (2)	C26—H26	0.9500
N5—N6	1.3031 (18)
O1W—Na1—O4W	169.11 (5)	C4—C3—C2	116.51 (15)
O1W—Na1—O3	90.96 (4)	C4—C3—H3	121.7
O4W—Na1—O3	98.12 (5)	C2—C3—H3	121.7
O1W—Na1—O7^i	85.13 (4)	N3—C4—C3	119.48 (15)
O4W—Na1—O7^i	101.30 (5)	N3—C4—H4	120.3
O3—Na1—O7^i	86.81 (4)	C3—C4—H4	120.3
O1W—Na1—O3W	87.73 (5)	C10—C5—C6	121.41 (15)
O4W—Na1—O3W	84.75 (6)	C10—C5—S1	117.89 (12)
O3—Na1—O3W	166.97 (5)	C6—C5—S1	120.71 (12)
O7^i—Na1—O3W	80.17 (5)	C7—C6—C5	118.90 (15)
O1W—Na1—O2W	81.14 (5)	C7—C6—H6	120.6
O4W—Na1—O2W	91.10 (6)	C5—C6—H6	120.6
O3—Na1—O2W	101.64 (5)	C6—C7—C8	119.27 (15)
O7^i—Na1—O2W	163.94 (5)	C6—C7—H7	120.4
O3W—Na1—O2W	90.97 (5)	C8—C7—H7	120.4
O2—S1—O1	116.71 (7)	C9—C8—C7	121.88 (15)
O2—S1—N1	104.29 (7)	C9—C8—N4	118.81 (15)
O1—S1—N1	113.65 (7)	C7—C8—N4	119.30 (14)
O2—S1—C5	106.55 (7)	C8—C9—C10	119.06 (15)
O1—S1—C5	108.68 (7)	C8—C9—H9	120.5
N1—S1—C5	106.26 (7)	C10—C9—H9	120.5
O4—S2—O5	115.51 (7)	C9—C10—C5	119.43 (15)
O4—S2—O6	111.69 (7)	C9—C10—H10	120.3
O5—S2—O6	110.45 (6)	C5—C10—H10	120.3
O4—S2—C17	108.60 (7)	N5—C11—C16	116.76 (13)
O5—S2—C17	105.90 (7)	N5—C11—C12	122.51 (13)
O6—S2—C17	103.85 (7)	C16—C11—C12	120.25 (13)
O8—S3—O7	113.59 (7)	O3—C12—C13	120.68 (13)
O8—S3—O9	112.90 (7)	O3—C12—C11	121.14 (14)
O7—S3—O9	112.34 (7)	C13—C12—C11	118.06 (13)
O8—S3—C19	105.75 (7)	C14—C13—C12	120.66 (14)
O7—S3—C19	105.76 (7)	C14—C13—H13	119.7
O9—S3—C19	105.67 (7)	C12—C13—H13	119.7
Na1—O1W—H1W	111.8 (16)	C13—C14—C15	122.71 (14)
Na1—O1W—H2W	121.3 (16)	C13—C14—H14	118.6
H1W—O1W—H2W	103 (2)	C15—C14—H14	118.6
C12—O3—Na1	136.93 (10)	C20—C15—C16	121.48 (13)
Na1—O2W—H3W	110.0 (18)	C20—C15—C14	118.39 (14)
Na1—O2W—H4W	124 (2)	C16—C15—C14	120.13 (13)
H3W—O2W—H4W	102 (3)	C15—C16—C17	116.75 (13)
Na1—O3W—H5W	119.2 (19)	C15—C16—C11	117.08 (13)
Na1—O3W—H6W	115 (2)	C17—C16—C11	126.18 (13)
H5W—O3W—H6W	100 (3)	C18—C17—C16	120.02 (14)
Na1—O4W—H7W	137.7 (16)	C18—C17—S2	113.36 (11)
Na1—O4W—H8W	108 (3)	C16—C17—S2	126.58 (11)
H7W—O4W—H8W	98 (2)	C17—C18—C19	121.74 (14)
Na1—O4W—H14W	118 (3)	C17—C18—H18	119.1
H7W—O4W—H14W	99 (2)	C19—C18—H18	119.1
H9W—O5W—H10W	99 (2)	C20—C19—C18	119.40 (14)
H11W—O6W—H12W	96 (2)	C20—C19—S3	121.46 (12)
S3—O7—Na1^i	138.42 (7)	C18—C19—S3	119.13 (11)
C1—N1—S1	123.67 (11)	C19—C20—C15	120.10 (14)
C2—N2—C1	117.89 (13)	C19—C20—H20	119.9
C4—N3—C1	122.12 (14)	C15—C20—H20	119.9
C4—N3—H5N	121.4 (15)	C22—C21—C26	121.42 (14)
C1—N3—H5N	116.4 (15)	C22—C21—N6	116.56 (13)
C8—N4—H2N	109.0 (15)	C26—C21—N6	122.01 (14)
C8—N4—H3N	109.8 (14)	C23—C22—C21	119.28 (15)
H2N—N4—H3N	111 (2)	C23—C22—H22	120.4
C8—N4—H4N	109.3 (14)	C21—C22—H22	120.4
H2N—N4—H4N	111 (2)	C22—C23—C24	120.15 (15)
H3N—N4—H4N	106.8 (19)	C22—C23—H23	119.9
N6—N5—C11	118.99 (13)	C24—C23—H23	119.9
N5—N6—C21	121.27 (13)	C23—C24—C25	119.87 (15)
N5—N6—H1N	115.4 (14)	C23—C24—H24	120.1
C21—N6—H1N	123.2 (14)	C25—C24—H24	120.1
N1—C1—N2	125.95 (14)	C26—C25—C24	121.02 (15)
N1—C1—N3	114.28 (14)	C26—C25—H25	119.5
N2—C1—N3	119.77 (14)	C24—C25—H25	119.5
N2—C2—C3	124.12 (15)	C25—C26—C21	118.25 (14)
N2—C2—H2	117.9	C25—C26—H26	120.9
C3—C2—H2	117.9	C21—C26—H26	120.9
O8—S3—O7—Na1^i	81.07 (11)	C13—C14—C15—C20	−178.66 (14)
O9—S3—O7—Na1^i	−149.26 (9)	C13—C14—C15—C16	1.2 (2)
C19—S3—O7—Na1^i	−34.46 (12)	C20—C15—C16—C17	6.9 (2)
O2—S1—N1—C1	156.92 (13)	C14—C15—C16—C17	−172.92 (13)
O1—S1—N1—C1	28.75 (15)	C20—C15—C16—C11	−172.79 (13)
C5—S1—N1—C1	−90.72 (14)	C14—C15—C16—C11	7.4 (2)
C11—N5—N6—C21	174.83 (13)	N5—C11—C16—C15	159.68 (13)
S1—N1—C1—N2	8.8 (2)	C12—C11—C16—C15	−12.5 (2)
S1—N1—C1—N3	−170.92 (11)	N5—C11—C16—C17	−20.0 (2)
C2—N2—C1—N1	−176.66 (15)	C12—C11—C16—C17	167.76 (14)
C2—N2—C1—N3	3.0 (2)	C15—C16—C17—C18	−7.1 (2)
C4—N3—C1—N1	175.88 (14)	C11—C16—C17—C18	172.62 (14)
C4—N3—C1—N2	−3.8 (2)	C15—C16—C17—S2	170.58 (11)
C1—N2—C2—C3	−0.2 (2)	C11—C16—C17—S2	−9.7 (2)
N2—C2—C3—C4	−1.9 (2)	O4—S2—C17—C18	141.14 (11)
C1—N3—C4—C3	1.6 (2)	O5—S2—C17—C18	−94.23 (12)
C2—C3—C4—N3	1.1 (2)	O6—S2—C17—C18	22.15 (13)
O2—S1—C5—C10	9.38 (14)	O4—S2—C17—C16	−36.66 (15)
O1—S1—C5—C10	135.92 (12)	O5—S2—C17—C16	87.97 (14)
N1—S1—C5—C10	−101.41 (13)	O6—S2—C17—C16	−155.65 (13)
O2—S1—C5—C6	−171.14 (12)	C16—C17—C18—C19	1.8 (2)
O1—S1—C5—C6	−44.60 (14)	S2—C17—C18—C19	−176.12 (11)
N1—S1—C5—C6	78.07 (14)	C17—C18—C19—C20	4.0 (2)
C10—C5—C6—C7	1.3 (2)	C17—C18—C19—S3	−174.87 (11)
S1—C5—C6—C7	−178.11 (12)	O8—S3—C19—C20	143.56 (13)
C5—C6—C7—C8	0.2 (2)	O7—S3—C19—C20	−95.67 (13)
C6—C7—C8—C9	−2.2 (2)	O9—S3—C19—C20	23.63 (14)
C6—C7—C8—N4	178.48 (14)	O8—S3—C19—C18	−37.62 (14)
C7—C8—C9—C10	2.5 (2)	O7—S3—C19—C18	83.15 (13)
N4—C8—C9—C10	−178.13 (14)	O9—S3—C19—C18	−157.55 (12)
C8—C9—C10—C5	−0.9 (2)	C18—C19—C20—C15	−4.2 (2)
C6—C5—C10—C9	−1.0 (2)	S3—C19—C20—C15	174.65 (11)
S1—C5—C10—C9	178.47 (12)	C16—C15—C20—C19	−1.4 (2)
N6—N5—C11—C16	−178.41 (12)	C14—C15—C20—C19	178.45 (13)
N6—N5—C11—C12	−6.4 (2)	N5—N6—C21—C22	−169.89 (13)
Na1—O3—C12—C13	6.3 (2)	N5—N6—C21—C26	10.6 (2)
Na1—O3—C12—C11	−169.80 (10)	C26—C21—C22—C23	0.9 (2)
N5—C11—C12—O3	13.8 (2)	N6—C21—C22—C23	−178.63 (14)
C16—C11—C12—O3	−174.40 (13)	C21—C22—C23—C24	0.1 (2)
N5—C11—C12—C13	−162.36 (14)	C22—C23—C24—C25	−0.7 (2)
C16—C11—C12—C13	9.4 (2)	C23—C24—C25—C26	0.5 (3)
O3—C12—C13—C14	−176.90 (14)	C24—C25—C26—C21	0.4 (2)
C11—C12—C13—C14	−0.7 (2)	C22—C21—C26—C25	−1.1 (2)
C12—C13—C14—C15	−4.7 (2)	N6—C21—C26—C25	178.40 (14)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O9^ii	0.88 (3)	1.99 (3)	2.8404 (16)	163 (2)
O1W—H2W···O1^ii	0.91 (3)	2.24 (3)	2.8830 (17)	127 (2)
O1W—H2W···N2^ii	0.91 (3)	2.07 (3)	2.8972 (18)	150 (2)
O2W—H3W···O9^ii	0.86 (3)	2.05 (3)	2.8852 (18)	163 (2)
O2W—H4W···O6^iii	0.92 (4)	1.98 (4)	2.8932 (18)	174 (3)
O3W—H5W···O5^iii	0.86 (3)	1.98 (3)	2.8320 (18)	178 (3)
O3W—H6W···O5W	0.83 (4)	2.18 (3)	2.736 (3)	124 (3)
O3W—H6W···O6W^iv	0.83 (4)	2.09 (4)	2.853 (3)	153 (3)
O3W—H6W···O7W^iv	0.83 (4)	2.06 (4)	2.799 (3)	148 (3)
O4W—H7W···O5^i	0.88 (1)	2.24 (1)	3.1093 (19)	169 (2)
O4W—H8W···O4W^iv	0.88 (1)	2.00 (2)	2.825 (3)	154 (4)
O4W—H8W···O6W	0.88 (1)	2.41 (5)	2.871 (3)	113 (4)
O4W—H14W···O7W^iv	0.89 (1)	2.16 (3)	2.902 (3)	140 (4)
O5W—H9W···O4^v	0.88 (1)	1.85 (1)	2.710 (3)	166 (4)
O5W—H10W···O8^i	0.89 (1)	1.99 (1)	2.843 (3)	163 (3)
O6W—H11W···O2^vi	0.89 (1)	2.22 (2)	2.893 (3)	132 (2)
O6W—H12W···O2W	0.88 (1)	1.85 (1)	2.731 (3)	178 (5)
O7W—H13W···O8^iii	0.88 (1)	1.91 (2)	2.699 (3)	150 (3)
N6—H1N···O3	0.92 (2)	1.75 (2)	2.5342 (16)	142 (2)
N4—H2N···O3W^vii	0.92 (3)	1.93 (3)	2.839 (2)	171 (2)
N4—H3N···O6	0.91 (2)	1.92 (2)	2.8245 (18)	170 (2)
N4—H4N···O1^viii	0.91 (2)	2.01 (2)	2.8784 (18)	159.6 (19)
N4—H4N···O1W^vii	0.91 (2)	2.50 (2)	2.9386 (19)	110.5 (16)
N3—H5N···O2^vi	0.84 (2)	2.57 (2)	3.0827 (17)	120.3 (18)
N3—H5N···N1^vi	0.84 (2)	2.02 (2)	2.8655 (19)	177 (2)

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

2-Aminopyridinium 4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline (V)

Crystal data

C5H7N2^+·C10H9N4O2S^−	F(000) = 720
Mr = 344.40	Dx = 1.454 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.5796 (2) Å	Cell parameters from 8493 reflections
b = 19.0371 (5) Å	θ = 3.0–29.5°
c = 11.2512 (4) Å	µ = 0.23 mm^−1
β = 121.116 (3)°	T = 123 K
V = 1573.27 (9) Å^3	Sheet, colourless
Z = 4	0.4 × 0.3 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer	3225 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.040
ω scans	θmax = 29.0°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −11→11
Tmin = 0.527, Tmax = 1.000	k = −25→25
22193 measured reflections	l = −14→15
4082 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 0.8192P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4082 reflections	Δρmax = 0.39 e Å^−3
237 parameters	Δρmin = −0.48 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.87444 (6)	0.84851 (2)	0.27777 (4)	0.02297 (12)
O1	0.97267 (17)	0.79251 (7)	0.25677 (14)	0.0309 (3)
O2	0.96376 (16)	0.87572 (7)	0.41782 (12)	0.0271 (3)
N1	0.83358 (19)	0.90544 (7)	0.16260 (15)	0.0233 (3)
N2	0.73473 (18)	1.01144 (7)	0.05571 (14)	0.0216 (3)
N3	0.71259 (19)	0.98683 (8)	0.25488 (15)	0.0239 (3)
N4	0.1507 (2)	0.73439 (9)	0.12033 (18)	0.0284 (3)
N5	1.20543 (19)	1.03376 (7)	0.15032 (15)	0.0231 (3)
N6	1.0916 (3)	1.14087 (10)	0.0502 (2)	0.0411 (4)
C1	0.7592 (2)	0.96881 (9)	0.16105 (17)	0.0209 (3)
C2	0.6662 (2)	1.07527 (9)	0.04854 (17)	0.0238 (4)
H2	0.6475	1.1057	−0.0247	0.029*
C3	0.6214 (2)	1.09897 (9)	0.14288 (18)	0.0258 (4)
H3	0.5754	1.1449	0.1382	0.031*
C4	0.6476 (2)	1.05165 (9)	0.24444 (18)	0.0258 (4)
H4	0.6175	1.0661	0.3110	0.031*
C5	0.6654 (2)	0.81161 (8)	0.23937 (17)	0.0215 (3)
C6	0.5823 (2)	0.76230 (9)	0.13303 (18)	0.0266 (4)
H6	0.6422	0.7470	0.0864	0.032*
C7	0.4129 (3)	0.73551 (9)	0.09498 (18)	0.0275 (4)
H7	0.3577	0.7015	0.0230	0.033*
C8	0.3216 (2)	0.75825 (8)	0.16202 (17)	0.0219 (3)
C9	0.4076 (2)	0.80709 (9)	0.26908 (17)	0.0235 (3)
H9	0.3488	0.8224	0.3164	0.028*
C10	0.5776 (2)	0.83359 (9)	0.30745 (17)	0.0235 (3)
H10	0.6342	0.8669	0.3806	0.028*
C11	1.1346 (2)	1.09647 (9)	0.15389 (18)	0.0251 (4)
C12	1.1082 (2)	1.10992 (10)	0.2655 (2)	0.0316 (4)
H12	1.0611	1.1540	0.2721	0.038*
C13	1.1499 (3)	1.06005 (11)	0.3633 (2)	0.0340 (4)
H13	1.1283	1.0688	0.4367	0.041*
C14	1.2247 (3)	0.99557 (11)	0.3572 (2)	0.0368 (5)
H14	1.2565	0.9607	0.4264	0.044*
C15	1.2502 (3)	0.98455 (10)	0.2496 (2)	0.0313 (4)
H15	1.3008	0.9412	0.2437	0.038*
H1N	0.109 (3)	0.6980 (12)	0.067 (2)	0.036 (6)*
H2N	0.100 (3)	0.7493 (12)	0.165 (2)	0.038 (6)*
H3N	1.220 (3)	1.0215 (12)	0.078 (2)	0.044 (6)*
H4N	1.045 (3)	1.1818 (14)	0.050 (3)	0.051 (7)*
H5N	1.105 (4)	1.1256 (13)	−0.021 (3)	0.060 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0214 (2)	0.0248 (2)	0.0239 (2)	0.00462 (16)	0.01254 (17)	0.00161 (16)
O1	0.0288 (7)	0.0315 (7)	0.0364 (7)	0.0096 (5)	0.0197 (6)	0.0023 (6)
O2	0.0236 (6)	0.0309 (7)	0.0230 (6)	0.0037 (5)	0.0092 (5)	0.0021 (5)
N1	0.0221 (7)	0.0251 (7)	0.0242 (7)	0.0019 (6)	0.0130 (6)	0.0013 (6)
N2	0.0188 (7)	0.0236 (7)	0.0215 (7)	−0.0033 (5)	0.0097 (6)	−0.0017 (5)
N3	0.0220 (7)	0.0278 (7)	0.0224 (7)	0.0011 (6)	0.0119 (6)	0.0000 (6)
N4	0.0302 (8)	0.0267 (8)	0.0333 (9)	−0.0041 (7)	0.0201 (7)	−0.0066 (7)
N5	0.0230 (7)	0.0257 (7)	0.0230 (7)	0.0009 (6)	0.0135 (6)	−0.0012 (6)
N6	0.0551 (12)	0.0302 (9)	0.0434 (11)	0.0162 (8)	0.0292 (10)	0.0084 (8)
C1	0.0161 (7)	0.0247 (8)	0.0203 (8)	−0.0027 (6)	0.0082 (6)	−0.0017 (6)
C2	0.0219 (8)	0.0241 (8)	0.0222 (8)	−0.0031 (7)	0.0092 (7)	0.0001 (7)
C3	0.0235 (8)	0.0219 (8)	0.0267 (9)	−0.0007 (7)	0.0092 (7)	−0.0045 (7)
C4	0.0215 (8)	0.0300 (9)	0.0247 (8)	−0.0001 (7)	0.0111 (7)	−0.0047 (7)
C5	0.0238 (8)	0.0199 (8)	0.0227 (8)	0.0031 (6)	0.0135 (7)	0.0024 (6)
C6	0.0310 (9)	0.0265 (8)	0.0288 (9)	0.0033 (7)	0.0201 (8)	−0.0030 (7)
C7	0.0322 (9)	0.0250 (8)	0.0270 (9)	−0.0013 (7)	0.0166 (8)	−0.0071 (7)
C8	0.0261 (8)	0.0183 (7)	0.0232 (8)	0.0027 (6)	0.0141 (7)	0.0044 (6)
C9	0.0304 (9)	0.0229 (8)	0.0234 (8)	0.0022 (7)	0.0183 (7)	0.0015 (7)
C10	0.0293 (9)	0.0228 (8)	0.0203 (8)	0.0014 (7)	0.0142 (7)	−0.0009 (6)
C11	0.0195 (8)	0.0253 (8)	0.0286 (9)	0.0006 (7)	0.0111 (7)	−0.0029 (7)
C12	0.0248 (9)	0.0353 (10)	0.0367 (10)	−0.0030 (8)	0.0173 (8)	−0.0133 (8)
C13	0.0268 (9)	0.0514 (12)	0.0281 (9)	−0.0147 (9)	0.0173 (8)	−0.0168 (9)
C14	0.0405 (11)	0.0416 (11)	0.0289 (10)	−0.0055 (9)	0.0185 (9)	0.0039 (8)
C15	0.0368 (10)	0.0270 (9)	0.0331 (10)	0.0041 (8)	0.0202 (9)	0.0033 (8)

Geometric parameters (Å, º)

S1—O2	1.4458 (13)	C3—H3	0.9500
S1—O1	1.4520 (12)	C4—H4	0.9500
S1—N1	1.5834 (15)	C5—C10	1.388 (2)
S1—C5	1.7592 (17)	C5—C6	1.393 (2)
N1—C1	1.361 (2)	C6—C7	1.383 (3)
N2—C2	1.334 (2)	C6—H6	0.9500
N2—C1	1.360 (2)	C7—C8	1.407 (2)
N3—C4	1.334 (2)	C7—H7	0.9500
N3—C1	1.352 (2)	C8—C9	1.393 (2)
N4—C8	1.366 (2)	C9—C10	1.384 (2)
N4—H1N	0.86 (2)	C9—H9	0.9500
N4—H2N	0.87 (2)	C10—H10	0.9500
N5—C11	1.349 (2)	C11—C12	1.410 (3)
N5—C15	1.353 (2)	C12—C13	1.354 (3)
N5—H3N	0.92 (2)	C12—H12	0.9500
N6—C11	1.329 (3)	C13—C14	1.403 (3)
N6—H4N	0.87 (3)	C13—H13	0.9500
N6—H5N	0.92 (3)	C14—C15	1.352 (3)
C2—C3	1.379 (2)	C14—H14	0.9500
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.379 (3)
O2—S1—O1	114.52 (8)	C6—C5—S1	118.99 (13)
O2—S1—N1	114.53 (8)	C7—C6—C5	120.28 (16)
O1—S1—N1	105.72 (8)	C7—C6—H6	119.9
O2—S1—C5	108.04 (8)	C5—C6—H6	119.9
O1—S1—C5	105.70 (8)	C6—C7—C8	120.50 (16)
N1—S1—C5	107.81 (8)	C6—C7—H7	119.7
C1—N1—S1	121.43 (12)	C8—C7—H7	119.7
C2—N2—C1	117.44 (14)	N4—C8—C9	120.93 (16)
C4—N3—C1	116.41 (15)	N4—C8—C7	120.64 (16)
C8—N4—H1N	119.2 (15)	C9—C8—C7	118.40 (16)
C8—N4—H2N	117.6 (15)	C10—C9—C8	121.00 (16)
H1N—N4—H2N	121 (2)	C10—C9—H9	119.5
C11—N5—C15	121.88 (16)	C8—C9—H9	119.5
C11—N5—H3N	121.5 (14)	C9—C10—C5	120.19 (16)
C15—N5—H3N	116.5 (14)	C9—C10—H10	119.9
C11—N6—H4N	119.3 (16)	C5—C10—H10	119.9
C11—N6—H5N	117.6 (16)	N6—C11—N5	117.51 (17)
H4N—N6—H5N	123 (2)	N6—C11—C12	124.49 (18)
N3—C1—N2	123.66 (15)	N5—C11—C12	117.99 (17)
N3—C1—N1	122.74 (15)	C13—C12—C11	119.97 (17)
N2—C1—N1	113.60 (14)	C13—C12—H12	120.0
N2—C2—C3	122.76 (16)	C11—C12—H12	120.0
N2—C2—H2	118.6	C12—C13—C14	120.61 (17)
C3—C2—H2	118.6	C12—C13—H13	119.7
C2—C3—C4	115.67 (16)	C14—C13—H13	119.7
C2—C3—H3	122.2	C15—C14—C13	117.98 (18)
C4—C3—H3	122.2	C15—C14—H14	121.0
N3—C4—C3	123.98 (16)	C13—C14—H14	121.0
N3—C4—H4	118.0	C14—C15—N5	121.55 (18)
C3—C4—H4	118.0	C14—C15—H15	119.2
C10—C5—C6	119.61 (16)	N5—C15—H15	119.2
C10—C5—S1	121.30 (13)
O2—S1—N1—C1	−46.01 (15)	C10—C5—C6—C7	0.2 (3)
O1—S1—N1—C1	−173.05 (13)	S1—C5—C6—C7	−176.15 (14)
C5—S1—N1—C1	74.26 (14)	C5—C6—C7—C8	0.7 (3)
C4—N3—C1—N2	−3.3 (2)	C6—C7—C8—N4	176.89 (16)
C4—N3—C1—N1	177.47 (15)	C6—C7—C8—C9	−1.3 (3)
C2—N2—C1—N3	2.2 (2)	N4—C8—C9—C10	−177.19 (16)
C2—N2—C1—N1	−178.51 (14)	C7—C8—C9—C10	1.0 (2)
S1—N1—C1—N3	−1.2 (2)	C8—C9—C10—C5	−0.1 (3)
S1—N1—C1—N2	179.50 (11)	C6—C5—C10—C9	−0.5 (3)
C1—N2—C2—C3	0.4 (2)	S1—C5—C10—C9	175.75 (13)
N2—C2—C3—C4	−1.6 (2)	C15—N5—C11—N6	−178.70 (18)
C1—N3—C4—C3	2.0 (2)	C15—N5—C11—C12	0.1 (3)
C2—C3—C4—N3	0.3 (3)	N6—C11—C12—C13	177.36 (19)
O2—S1—C5—C10	24.88 (16)	N5—C11—C12—C13	−1.4 (3)
O1—S1—C5—C10	147.91 (14)	C11—C12—C13—C14	1.9 (3)
N1—S1—C5—C10	−99.39 (15)	C12—C13—C14—C15	−1.2 (3)
O2—S1—C5—C6	−158.80 (13)	C13—C14—C15—N5	0.0 (3)
O1—S1—C5—C6	−35.78 (16)	C11—N5—C15—C14	0.6 (3)
N1—S1—C5—C6	76.93 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N···O2^i	0.86 (2)	2.04 (2)	2.895 (2)	168 (2)
N4—H2N···O1^ii	0.87 (2)	2.03 (2)	2.887 (2)	174 (2)
N5—H3N···N2^iii	0.92 (2)	1.85 (2)	2.758 (2)	174 (2)
N6—H4N···N4^iv	0.87 (3)	2.39 (3)	3.085 (2)	137 (2)
N6—H5N···N1^iii	0.92 (3)	2.00 (3)	2.918 (2)	173 (3)

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

Ethanolaminium 4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline monohydrate (VI)

Crystal data

C2H8NO^+·C10H9N4O2S^−·H2O	F(000) = 696
Mr = 329.38	Dx = 1.503 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7755 (4) Å	Cell parameters from 3829 reflections
b = 9.8979 (4) Å	θ = 3.2–29.5°
c = 11.5366 (4) Å	µ = 0.25 mm^−1
β = 93.508 (3)°	T = 123 K
V = 1456.08 (9) Å^3	Fragment, colourless
Z = 4	0.25 × 0.24 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer	2942 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.023
ω scans	θmax = 29.5°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −16→17
Tmin = 0.904, Tmax = 1.000	k = −12→12
7213 measured reflections	l = −15→15
3571 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 0.609P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3571 reflections	Δρmax = 0.45 e Å^−3
231 parameters	Δρmin = −0.47 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.22358 (3)	0.19320 (4)	0.61905 (3)	0.01162 (11)
O1	0.17136 (8)	0.31689 (11)	0.58001 (10)	0.0164 (2)
O2	0.20716 (8)	0.15689 (11)	0.73914 (9)	0.0150 (2)
O3	0.45324 (9)	−0.36122 (12)	0.56317 (11)	0.0195 (3)
O1W	0.04450 (10)	0.06888 (14)	0.88727 (13)	0.0264 (3)
N1	0.34262 (10)	0.21715 (13)	0.59377 (11)	0.0131 (3)
N2	0.51428 (10)	0.15350 (13)	0.58746 (11)	0.0146 (3)
N3	0.39549 (10)	0.00832 (13)	0.68028 (11)	0.0150 (3)
N4	0.06716 (12)	−0.25029 (16)	0.31048 (14)	0.0204 (3)
N5	0.33848 (11)	−0.55735 (15)	0.42864 (13)	0.0153 (3)
C1	0.41755 (11)	0.12192 (16)	0.62242 (13)	0.0125 (3)
C2	0.59122 (12)	0.06494 (17)	0.61312 (14)	0.0167 (3)
H2	0.6595	0.0845	0.5894	0.020*
C3	0.57580 (13)	−0.05364 (17)	0.67255 (14)	0.0178 (3)
H3	0.6312	−0.1156	0.6906	0.021*
C4	0.47525 (12)	−0.07671 (17)	0.70408 (14)	0.0169 (3)
H4	0.4617	−0.1575	0.7450	0.020*
C5	0.17356 (11)	0.06143 (15)	0.53090 (13)	0.0119 (3)
C6	0.14954 (12)	−0.06369 (16)	0.57665 (14)	0.0149 (3)
H6	0.1589	−0.0789	0.6579	0.018*
C7	0.11201 (12)	−0.16636 (17)	0.50398 (14)	0.0163 (3)
H7	0.0946	−0.2513	0.5359	0.020*
C8	0.09943 (11)	−0.14617 (16)	0.38370 (14)	0.0150 (3)
C9	0.12428 (12)	−0.01923 (16)	0.33835 (13)	0.0150 (3)
H9	0.1163	−0.0040	0.2570	0.018*
C10	0.16023 (11)	0.08336 (16)	0.41125 (13)	0.0141 (3)
H10	0.1760	0.1693	0.3800	0.017*
C11	0.34327 (12)	−0.37296 (17)	0.57033 (15)	0.0184 (3)
H11A	0.3136	−0.2833	0.5878	0.022*
H11B	0.3284	−0.4349	0.6347	0.022*
C12	0.29135 (12)	−0.42582 (16)	0.45860 (15)	0.0173 (3)
H12A	0.2153	−0.4374	0.4673	0.021*
H12B	0.3005	−0.3601	0.3953	0.021*
H1N	0.0376 (17)	−0.223 (2)	0.243 (2)	0.033 (6)*
H2N	0.0370 (17)	−0.313 (2)	0.3425 (19)	0.029 (6)*
H3N	0.4051 (17)	−0.550 (2)	0.4209 (17)	0.023 (5)*
H4N	0.3120 (17)	−0.587 (2)	0.360 (2)	0.031 (6)*
H5N	0.3293 (17)	−0.625 (2)	0.483 (2)	0.032 (6)*
H1H	0.4656 (19)	−0.297 (3)	0.518 (2)	0.043 (7)*
H1W	0.095 (2)	0.097 (3)	0.833 (3)	0.065 (9)*
H2W	0.070 (2)	0.106 (3)	0.950 (2)	0.046 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01262 (17)	0.01188 (19)	0.01020 (19)	0.00106 (13)	−0.00062 (13)	−0.00008 (14)
O1	0.0180 (5)	0.0138 (6)	0.0170 (6)	0.0038 (4)	−0.0017 (4)	0.0010 (5)
O2	0.0167 (5)	0.0185 (6)	0.0099 (5)	0.0023 (4)	0.0007 (4)	0.0001 (4)
O3	0.0162 (5)	0.0161 (6)	0.0254 (7)	−0.0015 (5)	−0.0037 (5)	0.0028 (5)
O1W	0.0229 (6)	0.0330 (8)	0.0227 (7)	−0.0010 (5)	−0.0029 (5)	−0.0036 (6)
N1	0.0127 (6)	0.0129 (6)	0.0135 (6)	0.0000 (5)	−0.0011 (5)	0.0009 (5)
N2	0.0147 (6)	0.0149 (7)	0.0139 (6)	−0.0009 (5)	−0.0006 (5)	−0.0016 (5)
N3	0.0179 (6)	0.0144 (7)	0.0126 (6)	0.0016 (5)	0.0012 (5)	0.0008 (5)
N4	0.0253 (7)	0.0185 (8)	0.0171 (8)	−0.0046 (6)	−0.0014 (6)	−0.0029 (6)
N5	0.0164 (7)	0.0161 (7)	0.0131 (7)	−0.0015 (5)	−0.0010 (5)	0.0014 (6)
C1	0.0149 (7)	0.0137 (7)	0.0085 (7)	−0.0005 (6)	−0.0017 (5)	−0.0032 (6)
C2	0.0135 (7)	0.0206 (8)	0.0158 (8)	0.0009 (6)	0.0002 (6)	−0.0049 (7)
C3	0.0199 (8)	0.0184 (8)	0.0148 (8)	0.0061 (6)	−0.0016 (6)	−0.0017 (6)
C4	0.0222 (8)	0.0147 (8)	0.0136 (8)	0.0026 (6)	−0.0004 (6)	−0.0002 (6)
C5	0.0096 (6)	0.0138 (7)	0.0122 (7)	0.0000 (5)	0.0000 (5)	−0.0008 (6)
C6	0.0149 (7)	0.0188 (8)	0.0109 (7)	0.0001 (6)	0.0013 (5)	0.0010 (6)
C7	0.0172 (7)	0.0155 (8)	0.0161 (8)	−0.0031 (6)	0.0017 (6)	0.0012 (6)
C8	0.0111 (7)	0.0170 (8)	0.0169 (8)	0.0007 (6)	0.0007 (6)	−0.0036 (6)
C9	0.0152 (7)	0.0194 (8)	0.0104 (7)	0.0022 (6)	0.0003 (6)	0.0003 (6)
C10	0.0135 (7)	0.0154 (7)	0.0134 (7)	0.0008 (6)	0.0007 (5)	0.0026 (6)
C11	0.0171 (7)	0.0202 (8)	0.0178 (8)	−0.0006 (6)	0.0000 (6)	−0.0022 (7)
C12	0.0168 (7)	0.0159 (8)	0.0187 (8)	−0.0007 (6)	−0.0021 (6)	−0.0002 (7)

Geometric parameters (Å, º)

S1—O1	1.4525 (11)	C2—C3	1.379 (2)
S1—O2	1.4588 (11)	C2—H2	0.9500
S1—N1	1.5838 (13)	C3—C4	1.376 (2)
S1—C5	1.7505 (15)	C3—H3	0.9500
O3—C11	1.4172 (19)	C4—H4	0.9500
O3—H1H	0.84 (3)	C5—C6	1.388 (2)
O1W—H1W	0.97 (3)	C5—C10	1.397 (2)
O1W—H2W	0.86 (3)	C6—C7	1.384 (2)
N1—C1	1.3694 (19)	C6—H6	0.9500
N2—C2	1.337 (2)	C7—C8	1.401 (2)
N2—C1	1.3596 (19)	C7—H7	0.9500
N3—C4	1.337 (2)	C8—C9	1.405 (2)
N3—C1	1.346 (2)	C9—C10	1.379 (2)
N4—C8	1.379 (2)	C9—H9	0.9500
N4—H1N	0.89 (2)	C10—H10	0.9500
N4—H2N	0.83 (2)	C11—C12	1.507 (2)
N5—C12	1.484 (2)	C11—H11A	0.9900
N5—H3N	0.86 (2)	C11—H11B	0.9900
N5—H4N	0.90 (2)	C12—H12A	0.9900
N5—H5N	0.93 (2)	C12—H12B	0.9900
O1—S1—O2	114.34 (7)	C3—C4—H4	118.2
O1—S1—N1	104.16 (7)	C6—C5—C10	119.86 (14)
O2—S1—N1	114.03 (7)	C6—C5—S1	121.69 (12)
O1—S1—C5	107.67 (7)	C10—C5—S1	118.44 (12)
O2—S1—C5	107.43 (7)	C7—C6—C5	120.08 (14)
N1—S1—C5	108.97 (7)	C7—C6—H6	120.0
C11—O3—H1H	108.9 (16)	C5—C6—H6	120.0
H1W—O1W—H2W	101 (2)	C6—C7—C8	120.63 (15)
C1—N1—S1	121.16 (11)	C6—C7—H7	119.7
C2—N2—C1	116.93 (14)	C8—C7—H7	119.7
C4—N3—C1	116.59 (13)	N4—C8—C7	120.77 (15)
C8—N4—H1N	113.6 (15)	N4—C8—C9	120.40 (15)
C8—N4—H2N	114.6 (15)	C7—C8—C9	118.78 (14)
H1N—N4—H2N	116 (2)	C10—C9—C8	120.39 (14)
C12—N5—H3N	111.5 (13)	C10—C9—H9	119.8
C12—N5—H4N	111.2 (14)	C8—C9—H9	119.8
H3N—N5—H4N	104.9 (19)	C9—C10—C5	120.26 (14)
C12—N5—H5N	114.0 (13)	C9—C10—H10	119.9
H3N—N5—H5N	107.1 (18)	C5—C10—H10	119.9
H4N—N5—H5N	107.5 (19)	O3—C11—C12	111.39 (13)
N3—C1—N2	124.11 (14)	O3—C11—H11A	109.4
N3—C1—N1	122.02 (13)	C12—C11—H11A	109.4
N2—C1—N1	113.87 (14)	O3—C11—H11B	109.4
N2—C2—C3	122.86 (15)	C12—C11—H11B	109.3
N2—C2—H2	118.6	H11A—C11—H11B	108.0
C3—C2—H2	118.6	N5—C12—C11	109.89 (13)
C4—C3—C2	115.90 (15)	N5—C12—H12A	109.7
C4—C3—H3	122.1	C11—C12—H12A	109.7
C2—C3—H3	122.1	N5—C12—H12B	109.7
N3—C4—C3	123.61 (15)	C11—C12—H12B	109.7
N3—C4—H4	118.2	H12A—C12—H12B	108.2
O1—S1—N1—C1	178.29 (12)	N1—S1—C5—C6	109.60 (13)
O2—S1—N1—C1	52.98 (14)	O1—S1—C5—C10	43.52 (13)
C5—S1—N1—C1	−67.02 (14)	O2—S1—C5—C10	167.11 (11)
C4—N3—C1—N2	0.3 (2)	N1—S1—C5—C10	−68.88 (13)
C4—N3—C1—N1	−179.55 (14)	C10—C5—C6—C7	−0.3 (2)
C2—N2—C1—N3	−0.1 (2)	S1—C5—C6—C7	−178.76 (12)
C2—N2—C1—N1	179.74 (13)	C5—C6—C7—C8	1.0 (2)
S1—N1—C1—N3	−4.7 (2)	C6—C7—C8—N4	176.66 (15)
S1—N1—C1—N2	175.48 (10)	C6—C7—C8—C9	−0.8 (2)
C1—N2—C2—C3	−0.2 (2)	N4—C8—C9—C10	−177.60 (14)
N2—C2—C3—C4	0.3 (2)	C7—C8—C9—C10	−0.1 (2)
C1—N3—C4—C3	−0.1 (2)	C8—C9—C10—C5	0.8 (2)
C2—C3—C4—N3	−0.1 (2)	C6—C5—C10—C9	−0.6 (2)
O1—S1—C5—C6	−138.00 (12)	S1—C5—C10—C9	177.88 (11)
O2—S1—C5—C6	−14.40 (14)	O3—C11—C12—N5	56.48 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N···O1W^i	0.89 (2)	2.34 (2)	3.173 (2)	156 (2)
N4—H2N···O1W^ii	0.83 (2)	2.58 (2)	3.293 (2)	144.1 (19)
N5—H3N···O3^iii	0.86 (2)	2.01 (2)	2.7762 (18)	147.2 (18)
N5—H4N···O2^ii	0.90 (2)	1.99 (2)	2.8488 (18)	159 (2)
N5—H4N···N3^ii	0.90 (2)	2.51 (2)	3.038 (2)	118.1 (17)
N5—H5N···O1^iv	0.93 (2)	2.44 (2)	3.1006 (18)	128.4 (17)
N5—H5N···N1^iv	0.93 (2)	2.02 (2)	2.933 (2)	167.3 (19)
O3—H1H···N2^v	0.84 (3)	1.90 (3)	2.7399 (19)	177 (2)
O1W—H1W···O2	0.97 (3)	1.94 (3)	2.9039 (17)	174 (3)
O1W—H2W···O1^vi	0.86 (3)	2.07 (3)	2.8997 (18)	163 (2)

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