Two mono­sodium salt hydrates of Colour Index Pigment Red 48

We report herein the crystal structures of a monohydrate of Colour Index Pigment Red 48 (P.R.48) (systematic name: mono­sodium 2-{2-[3-carb­oxy-2-oxo-1,2-di­hydro­naphthalen-1-yl­idene]hydrazin-1-yl}-4-chloro-5-methyl­benzene­sul­fon­ate monohydrate), Na⁺·C₁₈H₁₂ClO₆S⁻·H₂O, and a dihydrate, Na⁺·C₁₈H₁₂ClO₆S⁻·2H₂O. The two mono­sodium salt hydrates of P.R.48 were obtained from in-house synthesized P.R.48. Both have monoclinic (P2₁/c) symmetry at 173 K. The crystal packing of both crystal structures shows a layer arrangement whereby N—H...O and O—H...O hydrogen bonds are formed.

Computing details

Data collection: X-AREA (Stoe & Cie, 2001) for (I); APEX3 (Bruker, 2012) for (II). Cell refinement: X-AREA (Stoe & Cie, 2001) for (I); APEX3 (Bruker, 2012) for (II). Data reduction: X-AREA (Stoe & Cie, 2001) for (I); APEX3 (Bruker, 2012) for (II). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); SHELXT (Sheldrick, 2015a) for (II). Program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015) for (I); SHELXL2016 (Sheldrick, 2015b) for (II). Molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008) for (I); Mercury (Version 4.0; Macrae et al., 2020) and XP in SHELXTL-Plus (Sheldrick, 2008) for (II). Software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) for (I); publCIF (Westrip, 2010) for (II).

Sodium 2-{2-[3-carboxy-2-oxo-1,2-dihydronaphthalen-1-ylidene]hydrazin-1-yl}-4-chloro-5-methylbenzenesulfonate dihydrate (I)

Crystal data

Na^+·C18H12ClN2O6S^−·2H2O	F(000) = 984
Mr = 478.83	Dx = 1.664 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.5318 (9) Å	Cell parameters from 13702 reflections
b = 5.9396 (3) Å	θ = 3.4–26.0°
c = 17.4426 (10) Å	µ = 0.39 mm^−1
β = 95.528 (4)°	T = 173 K
V = 1911.00 (17) Å^3	Plate, red
Z = 4	0.19 × 0.09 × 0.02 mm

Data collection

Stoe IPDS II two-circle diffractometer	3009 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source, Genix 3D IµS microfocus X-ray source	Rint = 0.035
ω scans	θmax = 25.7°, θmin = 3.6°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −22→22
Tmin = 0.513, Tmax = 1.000	k = −7→6
13702 measured reflections	l = −21→21
3587 independent reflections

Refinement

Refinement on F^2	6 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0579P)^2 + 1.9026P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.001
3587 reflections	Δρmax = 0.44 e Å^−3
300 parameters	Δρmin = −0.41 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
Cl1	0.08560 (4)	−0.05322 (15)	0.45992 (5)	0.0340 (2)
S1	0.39354 (4)	0.39362 (12)	0.50777 (4)	0.01851 (18)
N1	0.26042 (12)	0.5591 (4)	0.39090 (13)	0.0163 (5)
H1	0.3023 (11)	0.627 (6)	0.394 (2)	0.030 (9)*
N2	0.20673 (12)	0.6300 (4)	0.34238 (13)	0.0168 (5)
O1	0.44371 (10)	0.2127 (4)	0.49657 (12)	0.0250 (5)
O2	0.39891 (12)	0.5848 (4)	0.45783 (13)	0.0324 (6)
O3	0.39582 (12)	0.4590 (4)	0.58882 (12)	0.0286 (5)
O4	0.33317 (11)	0.8989 (4)	0.34922 (12)	0.0238 (5)
O5	0.39225 (13)	1.2869 (5)	0.30846 (15)	0.0401 (6)
H5	0.419 (2)	1.402 (5)	0.305 (3)	0.060*
O6	0.33202 (13)	1.4851 (4)	0.21520 (13)	0.0328 (6)
C1	0.25012 (14)	0.3652 (5)	0.43408 (14)	0.0147 (5)
C2	0.30543 (14)	0.2760 (5)	0.48617 (15)	0.0160 (6)
C3	0.29177 (15)	0.0823 (5)	0.52743 (15)	0.0185 (6)
H3	0.330048	0.021750	0.561413	0.022*
C4	0.22550 (16)	−0.0268 (5)	0.52162 (15)	0.0185 (6)
C5	0.17136 (15)	0.0689 (5)	0.46987 (16)	0.0191 (6)
C6	0.18249 (15)	0.2572 (5)	0.42663 (15)	0.0192 (6)
H6	0.144349	0.314111	0.391689	0.023*
C7	0.21220 (17)	−0.2291 (6)	0.56951 (18)	0.0262 (7)
H7A	0.257787	−0.276126	0.598194	0.039*
H7B	0.193329	−0.352165	0.535911	0.039*
H7C	0.176795	−0.191501	0.605765	0.039*
C11	0.21339 (15)	0.8134 (5)	0.30069 (15)	0.0162 (6)
C12	0.27910 (15)	0.9540 (5)	0.30556 (15)	0.0178 (6)
C13	0.27637 (15)	1.1568 (5)	0.25780 (15)	0.0185 (6)
C14	0.21551 (16)	1.2067 (5)	0.21097 (16)	0.0205 (6)
H14	0.215290	1.340575	0.181149	0.025*
C15	0.15181 (15)	1.0693 (5)	0.20398 (15)	0.0193 (6)
C16	0.09208 (17)	1.1238 (6)	0.15046 (17)	0.0255 (7)
H16	0.092871	1.257974	0.120932	0.031*
C17	0.03307 (17)	0.9838 (6)	0.14101 (18)	0.0294 (7)
H17	−0.006263	1.019453	0.103999	0.035*
C18	0.03049 (17)	0.7893 (6)	0.18542 (18)	0.0274 (7)
H18	−0.010949	0.694467	0.179402	0.033*
C19	0.08837 (16)	0.7346 (5)	0.23829 (17)	0.0234 (6)
H19	0.086188	0.601815	0.268327	0.028*
C20	0.14987 (15)	0.8710 (5)	0.24827 (15)	0.0179 (6)
C21	0.33679 (17)	1.3222 (6)	0.25855 (17)	0.0257 (7)
Na1	0.45394 (6)	0.9200 (2)	0.40592 (7)	0.0267 (3)
O1W	0.54678 (13)	1.1339 (4)	0.35033 (13)	0.0309 (5)
H1WA	0.560 (2)	1.243 (5)	0.379 (2)	0.046*
H1WB	0.5816 (15)	1.112 (8)	0.323 (2)	0.046*
O2W	0.48388 (13)	0.6412 (4)	0.31108 (12)	0.0297 (5)
H2WA	0.5245 (12)	0.617 (7)	0.336 (2)	0.045*
H2WB	0.482 (2)	0.669 (7)	0.2632 (8)	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0222 (4)	0.0371 (5)	0.0417 (5)	−0.0141 (3)	−0.0023 (3)	0.0096 (4)
S1	0.0154 (3)	0.0172 (4)	0.0219 (3)	−0.0028 (3)	−0.0036 (3)	0.0018 (3)
N1	0.0158 (11)	0.0141 (12)	0.0183 (11)	−0.0031 (10)	−0.0014 (9)	0.0024 (9)
N2	0.0172 (11)	0.0155 (12)	0.0173 (11)	0.0010 (9)	−0.0005 (9)	−0.0015 (9)
O1	0.0167 (10)	0.0260 (12)	0.0314 (11)	0.0003 (9)	−0.0021 (8)	−0.0047 (9)
O2	0.0226 (11)	0.0299 (13)	0.0426 (13)	−0.0094 (10)	−0.0071 (9)	0.0163 (11)
O3	0.0278 (11)	0.0311 (13)	0.0260 (11)	−0.0060 (10)	−0.0023 (9)	−0.0091 (10)
O4	0.0214 (10)	0.0209 (11)	0.0277 (10)	−0.0029 (9)	−0.0047 (8)	0.0060 (9)
O5	0.0297 (13)	0.0359 (15)	0.0516 (15)	−0.0125 (11)	−0.0117 (11)	0.0162 (12)
O6	0.0329 (13)	0.0300 (13)	0.0350 (12)	−0.0056 (10)	0.0013 (10)	0.0123 (10)
C1	0.0163 (13)	0.0150 (14)	0.0131 (12)	−0.0008 (11)	0.0021 (10)	−0.0026 (10)
C2	0.0156 (13)	0.0151 (14)	0.0170 (12)	−0.0013 (11)	0.0000 (10)	−0.0023 (11)
C3	0.0225 (14)	0.0174 (15)	0.0154 (12)	0.0008 (12)	0.0002 (10)	0.0036 (11)
C4	0.0229 (14)	0.0169 (14)	0.0159 (13)	−0.0022 (12)	0.0029 (11)	0.0005 (11)
C5	0.0174 (13)	0.0206 (15)	0.0196 (13)	−0.0057 (12)	0.0036 (10)	−0.0021 (12)
C6	0.0183 (14)	0.0210 (16)	0.0180 (13)	0.0006 (12)	−0.0001 (11)	0.0000 (11)
C7	0.0301 (17)	0.0219 (16)	0.0268 (15)	−0.0040 (13)	0.0046 (12)	0.0034 (13)
C11	0.0187 (13)	0.0139 (14)	0.0161 (12)	0.0024 (11)	0.0021 (10)	−0.0014 (11)
C12	0.0189 (13)	0.0165 (14)	0.0177 (13)	0.0026 (11)	0.0006 (10)	0.0002 (11)
C13	0.0220 (14)	0.0160 (15)	0.0181 (13)	−0.0012 (11)	0.0049 (11)	−0.0024 (11)
C14	0.0287 (15)	0.0146 (14)	0.0188 (13)	0.0041 (12)	0.0058 (11)	0.0023 (11)
C15	0.0222 (14)	0.0190 (15)	0.0169 (13)	0.0048 (12)	0.0035 (11)	−0.0014 (11)
C16	0.0272 (16)	0.0247 (17)	0.0244 (15)	0.0057 (13)	0.0016 (12)	0.0048 (13)
C17	0.0225 (15)	0.0357 (19)	0.0283 (16)	0.0084 (14)	−0.0053 (12)	0.0014 (14)
C18	0.0192 (15)	0.0306 (18)	0.0321 (16)	−0.0015 (13)	0.0005 (12)	0.0000 (14)
C19	0.0208 (15)	0.0221 (16)	0.0268 (15)	0.0008 (12)	0.0005 (12)	0.0031 (12)
C20	0.0173 (13)	0.0182 (15)	0.0183 (13)	0.0054 (11)	0.0019 (10)	−0.0006 (11)
C21	0.0259 (16)	0.0298 (18)	0.0216 (14)	−0.0028 (13)	0.0030 (12)	−0.0003 (13)
Na1	0.0230 (6)	0.0278 (7)	0.0288 (6)	−0.0045 (5)	0.0009 (5)	−0.0056 (5)
O1W	0.0330 (13)	0.0290 (13)	0.0305 (12)	−0.0013 (10)	0.0019 (9)	−0.0082 (10)
O2W	0.0321 (12)	0.0308 (13)	0.0253 (11)	−0.0020 (10)	−0.0012 (9)	0.0023 (10)

Geometric parameters (Å, º)

Cl1—C5	1.740 (3)	C7—H7B	0.9800
S1—O2	1.441 (2)	C7—H7C	0.9800
S1—O1	1.447 (2)	C11—C20	1.460 (4)
S1—O3	1.463 (2)	C11—C12	1.472 (4)
S1—C2	1.783 (3)	C12—C13	1.463 (4)
N1—N2	1.312 (3)	C13—C14	1.360 (4)
N1—C1	1.399 (4)	C13—C21	1.489 (4)
N1—H1	0.872 (10)	C14—C15	1.431 (4)
N2—C11	1.322 (4)	C14—H14	0.9500
O1—Na1^i	2.370 (2)	C15—C20	1.411 (4)
O1—Na1^ii	2.548 (2)	C15—C16	1.415 (4)
O2—Na1	2.450 (3)	C16—C17	1.371 (5)
O4—C12	1.243 (3)	C16—H16	0.9500
O4—Na1	2.361 (2)	C17—C18	1.394 (5)
O5—C21	1.298 (4)	C17—H17	0.9500
O5—Na1	2.927 (3)	C18—C19	1.384 (4)
O5—H5	0.852 (10)	C18—H18	0.9500
O6—C21	1.226 (4)	C19—C20	1.395 (4)
C1—C6	1.403 (4)	C19—H19	0.9500
C1—C2	1.406 (4)	Na1—O1W	2.416 (3)
C2—C3	1.393 (4)	Na1—O2W	2.442 (3)
C3—C4	1.383 (4)	Na1—Na1^iii	3.675 (2)
C3—H3	0.9500	Na1—H2WA	2.59 (4)
C4—C5	1.404 (4)	O1W—H1WA	0.840 (10)
C4—C7	1.498 (4)	O1W—H1WB	0.846 (10)
C5—C6	1.375 (4)	O2W—H2WA	0.846 (10)
C6—H6	0.9500	O2W—H2WB	0.847 (10)
C7—H7A	0.9800
O2—S1—O1	114.91 (14)	C15—C16—H16	119.8
O2—S1—O3	112.21 (15)	C16—C17—C18	120.4 (3)
O1—S1—O3	111.63 (13)	C16—C17—H17	119.8
O2—S1—C2	107.25 (13)	C18—C17—H17	119.8
O1—S1—C2	105.52 (13)	C19—C18—C17	119.9 (3)
O3—S1—C2	104.42 (13)	C19—C18—H18	120.0
N2—N1—C1	118.5 (2)	C17—C18—H18	120.0
N2—N1—H1	120 (2)	C18—C19—C20	121.2 (3)
C1—N1—H1	121 (2)	C18—C19—H19	119.4
N1—N2—C11	120.9 (2)	C20—C19—H19	119.4
S1—O1—Na1^i	136.80 (12)	C19—C20—C15	118.7 (3)
S1—O1—Na1^ii	125.90 (12)	C19—C20—C11	122.8 (3)
Na1^i—O1—Na1^ii	96.68 (8)	C15—C20—C11	118.5 (3)
S1—O2—Na1	156.88 (13)	O6—C21—O5	123.1 (3)
C12—O4—Na1	156.7 (2)	O6—C21—C13	120.4 (3)
C21—O5—Na1	138.5 (2)	O5—C21—C13	116.4 (3)
C21—O5—H5	105 (3)	O4—Na1—O1^iv	100.66 (8)
Na1—O5—H5	116 (3)	O4—Na1—O1W	122.87 (9)
N1—C1—C6	119.6 (2)	O1^iv—Na1—O1W	89.30 (9)
N1—C1—C2	122.0 (2)	O4—Na1—O2W	87.03 (8)
C6—C1—C2	118.5 (3)	O1^iv—Na1—O2W	170.91 (9)
C3—C2—C1	119.2 (2)	O1W—Na1—O2W	82.41 (9)
C3—C2—S1	115.0 (2)	O4—Na1—O2	72.55 (8)
C1—C2—S1	125.8 (2)	O1^iv—Na1—O2	106.65 (9)
C4—C3—C2	123.6 (3)	O1W—Na1—O2	156.02 (10)
C4—C3—H3	118.2	O2W—Na1—O2	80.15 (9)
C2—C3—H3	118.2	O4—Na1—O1^ii	151.38 (9)
C3—C4—C5	115.6 (3)	O1^iv—Na1—O1^ii	83.32 (8)
C3—C4—C7	121.8 (3)	O1W—Na1—O1^ii	85.27 (8)
C5—C4—C7	122.5 (3)	O2W—Na1—O1^ii	92.26 (8)
C6—C5—C4	123.1 (3)	O2—Na1—O1^ii	79.14 (8)
C6—C5—Cl1	117.9 (2)	O4—Na1—O5	59.67 (7)
C4—C5—Cl1	119.0 (2)	O1^iv—Na1—O5	77.86 (9)
C5—C6—C1	120.1 (3)	O1W—Na1—O5	68.21 (8)
C5—C6—H6	120.0	O2W—Na1—O5	102.30 (9)
C1—C6—H6	120.0	O2—Na1—O5	131.78 (8)
C4—C7—H7A	109.5	O1^ii—Na1—O5	147.34 (8)
C4—C7—H7B	109.5	O4—Na1—Na1^iii	136.69 (8)
H7A—C7—H7B	109.5	O1^iv—Na1—Na1^iii	43.50 (5)
C4—C7—H7C	109.5	O1W—Na1—Na1^iii	86.27 (7)
H7A—C7—H7C	109.5	O2W—Na1—Na1^iii	131.60 (8)
H7B—C7—H7C	109.5	O2—Na1—Na1^iii	93.10 (7)
N2—C11—C20	115.2 (2)	O1^ii—Na1—Na1^iii	39.82 (5)
N2—C11—C12	123.8 (2)	O5—Na1—Na1^iii	116.61 (8)
C20—C11—C12	121.0 (2)	O4—Na1—H2WA	105.5 (5)
O4—C12—C13	123.2 (3)	O1^iv—Na1—H2WA	153.9 (5)
O4—C12—C11	120.0 (3)	O1W—Na1—H2WA	76.5 (9)
C13—C12—C11	116.8 (2)	O2W—Na1—H2WA	19.0 (4)
C14—C13—C12	120.2 (3)	O2—Na1—H2WA	81.7 (10)
C14—C13—C21	116.2 (3)	O1^ii—Na1—H2WA	73.9 (4)
C12—C13—C21	123.6 (2)	O5—Na1—H2WA	115.5 (7)
C13—C14—C15	123.8 (3)	Na1^iii—Na1—H2WA	112.7 (4)
C13—C14—H14	118.1	Na1—O1W—H1WA	110 (3)
C15—C14—H14	118.1	Na1—O1W—H1WB	139 (3)
C20—C15—C16	119.5 (3)	H1WA—O1W—H1WB	105 (4)
C20—C15—C14	119.6 (2)	Na1—O2W—H2WA	91 (3)
C16—C15—C14	120.8 (3)	Na1—O2W—H2WB	123 (3)
C17—C16—C15	120.3 (3)	H2WA—O2W—H2WB	120 (4)
C17—C16—H16	119.8
C1—N1—N2—C11	179.4 (2)	Na1—O4—C12—C13	−6.7 (7)
O2—S1—O1—Na1^i	−76.3 (2)	Na1—O4—C12—C11	173.9 (4)
O3—S1—O1—Na1^i	154.45 (18)	N2—C11—C12—O4	2.1 (4)
C2—S1—O1—Na1^i	41.6 (2)	C20—C11—C12—O4	−178.3 (3)
O2—S1—O1—Na1^ii	114.97 (16)	N2—C11—C12—C13	−177.4 (3)
O3—S1—O1—Na1^ii	−14.3 (2)	C20—C11—C12—C13	2.3 (4)
C2—S1—O1—Na1^ii	−127.10 (15)	O4—C12—C13—C14	179.7 (3)
O1—S1—O2—Na1	−68.7 (4)	C11—C12—C13—C14	−0.8 (4)
O3—S1—O2—Na1	60.3 (5)	O4—C12—C13—C21	−2.3 (4)
C2—S1—O2—Na1	174.4 (4)	C11—C12—C13—C21	177.2 (3)
N2—N1—C1—C6	−2.3 (4)	C12—C13—C14—C15	−0.7 (4)
N2—N1—C1—C2	178.7 (2)	C21—C13—C14—C15	−178.9 (3)
N1—C1—C2—C3	−180.0 (2)	C13—C14—C15—C20	0.9 (4)
C6—C1—C2—C3	1.1 (4)	C13—C14—C15—C16	−175.9 (3)
N1—C1—C2—S1	2.1 (4)	C20—C15—C16—C17	−0.7 (4)
C6—C1—C2—S1	−176.9 (2)	C14—C15—C16—C17	176.1 (3)
O2—S1—C2—C3	177.6 (2)	C15—C16—C17—C18	1.7 (5)
O1—S1—C2—C3	54.6 (2)	C16—C17—C18—C19	−1.3 (5)
O3—S1—C2—C3	−63.2 (2)	C17—C18—C19—C20	0.0 (5)
O2—S1—C2—C1	−4.4 (3)	C18—C19—C20—C15	0.9 (4)
O1—S1—C2—C1	−127.3 (2)	C18—C19—C20—C11	−176.9 (3)
O3—S1—C2—C1	114.9 (3)	C16—C15—C20—C19	−0.5 (4)
C1—C2—C3—C4	−1.6 (4)	C14—C15—C20—C19	−177.4 (3)
S1—C2—C3—C4	176.6 (2)	C16—C15—C20—C11	177.4 (3)
C2—C3—C4—C5	0.7 (4)	C14—C15—C20—C11	0.5 (4)
C2—C3—C4—C7	−177.4 (3)	N2—C11—C20—C19	−4.6 (4)
C3—C4—C5—C6	0.7 (4)	C12—C11—C20—C19	175.7 (3)
C7—C4—C5—C6	178.7 (3)	N2—C11—C20—C15	177.6 (2)
C3—C4—C5—Cl1	−178.8 (2)	C12—C11—C20—C15	−2.1 (4)
C7—C4—C5—Cl1	−0.7 (4)	Na1—O5—C21—O6	−165.5 (2)
C4—C5—C6—C1	−1.1 (4)	Na1—O5—C21—C13	16.5 (5)
Cl1—C5—C6—C1	178.3 (2)	C14—C13—C21—O6	−4.4 (4)
N1—C1—C6—C5	−178.8 (2)	C12—C13—C21—O6	177.6 (3)
C2—C1—C6—C5	0.2 (4)	C14—C13—C21—O5	173.6 (3)
N1—N2—C11—C20	179.1 (2)	C12—C13—C21—O5	−4.4 (4)
N1—N2—C11—C12	−1.2 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.87 (1)	2.03 (3)	2.720 (3)	135 (3)
N1—H1···O4	0.87 (1)	1.90 (3)	2.570 (3)	132 (3)
O5—H5···O2W^iv	0.85 (1)	1.86 (1)	2.702 (3)	172 (5)
O1W—H1WA···O3^iii	0.84 (1)	2.01 (2)	2.808 (3)	159 (4)
O1W—H1WB···O6^v	0.85 (1)	1.95 (2)	2.762 (3)	162 (4)
O2W—H2WA···O3^ii	0.85 (1)	1.93 (1)	2.761 (3)	167 (4)
O2W—H2WB···O1W^v	0.85 (1)	2.01 (2)	2.818 (3)	159 (4)

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

Sodium 2-{2-[3-carboxy-2-oxo-1,2-dihydronaphthalen-1-ylidene]hydrazin-1-yl}-4-chloro-5-methylbenzenesulfonate monohydrate (II)

Crystal data

Na^+·C18H12ClN2O6S^−·H2O	F(000) = 944
Mr = 460.81	Dx = 1.668 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 18.2222 (2) Å	Cell parameters from 4687 reflections
b = 5.9486 (1) Å	θ = 2.4–67.7°
c = 16.9361 (2) Å	µ = 3.59 mm^−1
β = 92.037 (1)°	T = 173 K
V = 1834.66 (4) Å^3	Plate, red
Z = 4	0.33 × 0.03 × 0.02 mm

Data collection

Siemens CCD three-circle diffractometer	3049 reflections with I > 2σ(I)
Radiation source: Sealed X-ray tube, Incoatec Microfocus tube	Rint = 0.046
ω scans	θmax = 70.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→21
Tmin = 0.556, Tmax = 1.000	k = −6→7
12502 measured reflections	l = −20→18
3314 independent reflections

Refinement

Refinement on F^2	5 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0916P)^2 + 1.5536P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
3314 reflections	Δρmax = 0.48 e Å^−3
284 parameters	Δρmin = −0.89 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	0.46699 (6)	0.11912 (18)	0.39837 (7)	0.0299 (3)
C11	0.22753 (13)	0.1729 (4)	0.28548 (13)	0.0153 (5)
C12	0.29718 (13)	0.0461 (4)	0.28380 (13)	0.0156 (5)
O4	0.35120 (10)	0.1045 (3)	0.32556 (10)	0.0205 (4)
C13	0.29668 (13)	−0.1543 (4)	0.23321 (13)	0.0166 (5)
C21	0.36533 (14)	−0.2866 (4)	0.22202 (13)	0.0192 (5)
O5	0.42699 (10)	−0.2073 (3)	0.22602 (12)	0.0283 (4)
O6	0.35100 (10)	−0.4969 (3)	0.20382 (12)	0.0247 (4)
H61A	0.3883 (14)	−0.573 (5)	0.193 (2)	0.030*
C14	0.23422 (14)	−0.2204 (4)	0.19440 (14)	0.0186 (5)
H14	0.235408	−0.356513	0.165142	0.022*
C15	0.16616 (13)	−0.0983 (4)	0.19448 (14)	0.0164 (5)
C16	0.10515 (14)	−0.1669 (5)	0.14716 (15)	0.0229 (5)
H16	0.107611	−0.301727	0.117308	0.028*
C17	0.04215 (15)	−0.0404 (5)	0.14384 (16)	0.0276 (6)
H17	0.001324	−0.086386	0.111321	0.033*
C18	0.03838 (14)	0.1557 (5)	0.18837 (17)	0.0264 (6)
H18	−0.005286	0.243085	0.185960	0.032*
C19	0.09718 (14)	0.2252 (4)	0.23600 (15)	0.0216 (5)
H19	0.093298	0.357910	0.266768	0.026*
C20	0.16268 (13)	0.1006 (4)	0.23916 (13)	0.0158 (5)
N2	0.21776 (11)	0.3552 (3)	0.32809 (11)	0.0153 (4)
N1	0.27125 (11)	0.4409 (3)	0.37237 (11)	0.0147 (4)
H1	0.3129 (12)	0.375 (5)	0.3722 (18)	0.018*
C1	0.25658 (13)	0.6350 (4)	0.41548 (13)	0.0135 (5)
C6	0.18668 (13)	0.7313 (4)	0.41065 (14)	0.0180 (5)
H6	0.149287	0.666809	0.377345	0.022*
C5	0.17222 (13)	0.9204 (4)	0.45439 (14)	0.0178 (5)
Cl1	0.08338 (4)	1.02827 (12)	0.44881 (4)	0.0321 (2)
C4	0.22504 (13)	1.0271 (4)	0.50287 (14)	0.0169 (5)
C7	0.20863 (15)	1.2326 (4)	0.55051 (15)	0.0241 (6)
H7A	0.254363	1.291794	0.574560	0.036*
H7B	0.174888	1.193090	0.592111	0.036*
H7C	0.185906	1.347104	0.515968	0.036*
C3	0.29440 (13)	0.9286 (4)	0.50606 (13)	0.0162 (5)
H3	0.332158	0.997124	0.537807	0.019*
C2	0.31060 (12)	0.7347 (4)	0.46482 (13)	0.0139 (5)
S1	0.39923 (3)	0.61529 (9)	0.48312 (3)	0.0155 (2)
O2	0.41769 (9)	0.4932 (3)	0.41226 (11)	0.0255 (4)
O1	0.39128 (11)	0.4700 (4)	0.55081 (13)	0.0348 (5)
O3	0.44656 (9)	0.8078 (3)	0.49875 (11)	0.0232 (4)
O1W	0.53394 (10)	−0.1893 (3)	0.34443 (11)	0.0232 (4)
H1WB	0.5487 (16)	−0.300 (3)	0.3717 (15)	0.028*
H1WA	0.5039 (14)	−0.229 (4)	0.3081 (13)	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na1	0.0279 (6)	0.0239 (6)	0.0370 (6)	0.0055 (4)	−0.0104 (5)	−0.0078 (4)
C11	0.0211 (11)	0.0129 (11)	0.0121 (10)	−0.0021 (9)	0.0038 (8)	0.0015 (9)
C12	0.0221 (12)	0.0139 (11)	0.0110 (10)	−0.0004 (9)	0.0015 (8)	0.0036 (9)
O4	0.0227 (9)	0.0186 (9)	0.0198 (9)	0.0010 (7)	−0.0056 (7)	−0.0035 (7)
C13	0.0240 (12)	0.0141 (11)	0.0121 (11)	0.0008 (9)	0.0030 (9)	0.0008 (9)
C21	0.0257 (12)	0.0204 (13)	0.0115 (11)	0.0000 (10)	0.0002 (9)	−0.0009 (9)
O5	0.0218 (9)	0.0265 (10)	0.0362 (11)	−0.0002 (8)	−0.0040 (8)	−0.0009 (8)
O6	0.0243 (9)	0.0165 (9)	0.0337 (11)	0.0022 (7)	0.0078 (8)	−0.0058 (8)
C14	0.0257 (12)	0.0174 (12)	0.0130 (11)	−0.0013 (10)	0.0041 (9)	−0.0023 (9)
C15	0.0227 (12)	0.0133 (11)	0.0136 (11)	−0.0032 (9)	0.0036 (9)	0.0005 (9)
C16	0.0264 (13)	0.0213 (13)	0.0212 (12)	−0.0068 (11)	0.0020 (10)	−0.0064 (10)
C17	0.0211 (12)	0.0358 (16)	0.0258 (14)	−0.0068 (11)	−0.0028 (10)	−0.0049 (12)
C18	0.0202 (12)	0.0309 (14)	0.0282 (13)	−0.0008 (11)	0.0007 (10)	−0.0023 (11)
C19	0.0220 (12)	0.0233 (13)	0.0196 (12)	−0.0014 (10)	0.0026 (9)	−0.0035 (10)
C20	0.0216 (12)	0.0160 (12)	0.0099 (10)	−0.0010 (9)	0.0034 (8)	0.0024 (9)
N2	0.0201 (10)	0.0165 (10)	0.0094 (9)	−0.0020 (8)	0.0006 (7)	0.0004 (7)
N1	0.0175 (10)	0.0135 (10)	0.0132 (9)	0.0016 (8)	0.0003 (7)	−0.0020 (8)
C1	0.0206 (11)	0.0111 (11)	0.0088 (10)	0.0000 (9)	0.0028 (8)	0.0018 (8)
C6	0.0202 (12)	0.0201 (12)	0.0136 (11)	0.0012 (10)	−0.0004 (9)	0.0007 (9)
C5	0.0197 (11)	0.0193 (12)	0.0145 (11)	0.0052 (9)	0.0044 (9)	0.0042 (9)
Cl1	0.0247 (4)	0.0364 (4)	0.0348 (4)	0.0151 (3)	−0.0008 (3)	−0.0057 (3)
C4	0.0255 (12)	0.0133 (11)	0.0123 (11)	0.0018 (9)	0.0067 (9)	0.0015 (9)
C7	0.0322 (14)	0.0203 (13)	0.0205 (12)	0.0026 (11)	0.0098 (10)	−0.0039 (10)
C3	0.0229 (12)	0.0138 (11)	0.0121 (10)	−0.0024 (9)	0.0024 (9)	0.0000 (9)
C2	0.0177 (11)	0.0140 (11)	0.0104 (10)	0.0014 (9)	0.0034 (8)	0.0017 (8)
S1	0.0157 (3)	0.0138 (3)	0.0170 (3)	0.0002 (2)	−0.0001 (2)	−0.0013 (2)
O2	0.0194 (9)	0.0270 (10)	0.0302 (10)	0.0029 (7)	0.0021 (7)	−0.0134 (8)
O1	0.0256 (10)	0.0409 (12)	0.0378 (12)	0.0062 (9)	0.0011 (8)	0.0212 (10)
O3	0.0199 (8)	0.0201 (9)	0.0296 (10)	−0.0019 (7)	−0.0009 (7)	−0.0097 (7)
O1W	0.0256 (9)	0.0242 (10)	0.0199 (9)	−0.0047 (8)	0.0000 (7)	0.0051 (7)

Geometric parameters (Å, º)

Na1—O3^i	2.348 (2)	C18—H18	0.9500
Na1—O1W	2.402 (2)	C19—C20	1.404 (4)
Na1—O4	2.4074 (19)	C19—H19	0.9500
Na1—O2	2.414 (2)	N2—N1	1.312 (3)
Na1—O3^ii	2.550 (2)	N1—C1	1.397 (3)
Na1—Na1^iii	3.874 (2)	N1—H1	0.855 (18)
Na1—H1WA	2.67 (3)	C1—C6	1.397 (3)
C11—N2	1.318 (3)	C1—C2	1.400 (3)
C11—C20	1.460 (3)	C6—C5	1.377 (4)
C11—C12	1.477 (3)	C6—H6	0.9500
C12—O4	1.241 (3)	C5—C4	1.395 (4)
C12—C13	1.468 (3)	C5—Cl1	1.741 (2)
C13—C14	1.352 (3)	C4—C3	1.392 (3)
C13—C21	1.496 (3)	C4—C7	1.501 (3)
C21—O5	1.218 (3)	C7—H7A	0.9800
C21—O6	1.312 (3)	C7—H7B	0.9800
O6—H61A	0.843 (18)	C7—H7C	0.9800
C14—C15	1.437 (4)	C3—C2	1.386 (3)
C14—H14	0.9500	C3—H3	0.9500
C15—C20	1.407 (3)	C2—S1	1.781 (2)
C15—C16	1.408 (3)	S1—O1	1.447 (2)
C16—C17	1.372 (4)	S1—O3	1.4524 (18)
C16—H16	0.9500	S1—O2	1.4525 (19)
C17—C18	1.392 (4)	O1W—H1WB	0.844 (10)
C17—H17	0.9500	O1W—H1WA	0.843 (10)
C18—C19	1.381 (4)
O3^i—Na1—O1W	95.00 (7)	C17—C18—H18	119.5
O3^i—Na1—O4	159.99 (8)	C18—C19—C20	120.3 (2)
O1W—Na1—O4	103.02 (7)	C18—C19—H19	119.8
O3^i—Na1—O2	89.96 (7)	C20—C19—H19	119.8
O1W—Na1—O2	159.55 (9)	C19—C20—C15	118.5 (2)
O4—Na1—O2	76.16 (6)	C19—C20—C11	122.4 (2)
O3^i—Na1—O3^ii	75.50 (7)	C15—C20—C11	119.1 (2)
O1W—Na1—O3^ii	77.70 (7)	N1—N2—C11	121.4 (2)
O4—Na1—O3^ii	99.73 (7)	N2—N1—C1	117.90 (19)
O2—Na1—O3^ii	122.73 (8)	N2—N1—H1	117 (2)
O3^i—Na1—Na1^iii	39.58 (5)	C1—N1—H1	125 (2)
O1W—Na1—Na1^iii	84.99 (6)	C6—C1—N1	120.0 (2)
O4—Na1—Na1^iii	132.89 (7)	C6—C1—C2	118.8 (2)
O2—Na1—Na1^iii	110.82 (7)	N1—C1—C2	121.2 (2)
O3^ii—Na1—Na1^iii	35.92 (4)	C5—C6—C1	119.7 (2)
O3^i—Na1—H1WA	113.1 (3)	C5—C6—H6	120.2
O1W—Na1—H1WA	18.1 (3)	C1—C6—H6	120.2
O4—Na1—H1WA	85.0 (4)	C6—C5—C4	123.1 (2)
O2—Na1—H1WA	150.7 (4)	C6—C5—Cl1	117.85 (19)
O3^ii—Na1—H1WA	82.2 (6)	C4—C5—Cl1	119.01 (19)
Na1^iii—Na1—H1WA	98.5 (4)	C3—C4—C5	116.0 (2)
N2—C11—C20	114.5 (2)	C3—C4—C7	121.3 (2)
N2—C11—C12	124.3 (2)	C5—C4—C7	122.7 (2)
C20—C11—C12	121.2 (2)	C4—C7—H7A	109.5
O4—C12—C13	123.2 (2)	C4—C7—H7B	109.5
O4—C12—C11	120.7 (2)	H7A—C7—H7B	109.5
C13—C12—C11	116.0 (2)	C4—C7—H7C	109.5
C12—O4—Na1	164.81 (16)	H7A—C7—H7C	109.5
C14—C13—C12	120.5 (2)	H7B—C7—H7C	109.5
C14—C13—C21	118.6 (2)	C2—C3—C4	122.7 (2)
C12—C13—C21	120.9 (2)	C2—C3—H3	118.7
O5—C21—O6	123.9 (2)	C4—C3—H3	118.7
O5—C21—C13	124.2 (2)	C3—C2—C1	119.7 (2)
O6—C21—C13	111.8 (2)	C3—C2—S1	116.89 (18)
C21—O6—H61A	114 (2)	C1—C2—S1	123.28 (18)
C13—C14—C15	124.3 (2)	O1—S1—O3	113.71 (12)
C13—C14—H14	117.8	O1—S1—O2	112.86 (13)
C15—C14—H14	117.8	O3—S1—O2	113.05 (11)
C20—C15—C16	120.0 (2)	O1—S1—C2	105.09 (11)
C20—C15—C14	118.7 (2)	O3—S1—C2	104.25 (11)
C16—C15—C14	121.1 (2)	O2—S1—C2	106.91 (10)
C17—C16—C15	120.5 (2)	S1—O2—Na1	129.75 (12)
C17—C16—H16	119.8	S1—O3—Na1^i	131.28 (12)
C15—C16—H16	119.8	S1—O3—Na1^iv	123.43 (10)
C16—C17—C18	119.7 (2)	Na1^i—O3—Na1^iv	104.50 (7)
C16—C17—H17	120.2	Na1—O1W—H1WB	123 (2)
C18—C17—H17	120.2	Na1—O1W—H1WA	100 (2)
C19—C18—C17	121.0 (3)	H1WB—O1W—H1WA	111.4 (17)
C19—C18—H18	119.5
N2—C11—C12—O4	1.9 (4)	C11—N2—N1—C1	179.7 (2)
C20—C11—C12—O4	−177.4 (2)	N2—N1—C1—C6	0.1 (3)
N2—C11—C12—C13	179.3 (2)	N2—N1—C1—C2	179.2 (2)
C20—C11—C12—C13	0.0 (3)	N1—C1—C6—C5	178.9 (2)
C13—C12—O4—Na1	−13.1 (8)	C2—C1—C6—C5	−0.3 (3)
C11—C12—O4—Na1	164.1 (5)	C1—C6—C5—C4	1.7 (4)
O4—C12—C13—C14	174.1 (2)	C1—C6—C5—Cl1	−177.86 (18)
C11—C12—C13—C14	−3.1 (3)	C6—C5—C4—C3	−1.1 (3)
O4—C12—C13—C21	−7.2 (4)	Cl1—C5—C4—C3	178.43 (17)
C11—C12—C13—C21	175.5 (2)	C6—C5—C4—C7	−179.8 (2)
C14—C13—C21—O5	150.0 (2)	Cl1—C5—C4—C7	−0.2 (3)
C12—C13—C21—O5	−28.6 (4)	C5—C4—C3—C2	−0.9 (3)
C14—C13—C21—O6	−27.1 (3)	C7—C4—C3—C2	177.8 (2)
C12—C13—C21—O6	154.3 (2)	C4—C3—C2—C1	2.2 (4)
C12—C13—C14—C15	4.2 (4)	C4—C3—C2—S1	−173.88 (18)
C21—C13—C14—C15	−174.5 (2)	C6—C1—C2—C3	−1.6 (3)
C13—C14—C15—C20	−1.7 (4)	N1—C1—C2—C3	179.3 (2)
C13—C14—C15—C16	174.4 (2)	C6—C1—C2—S1	174.25 (17)
C20—C15—C16—C17	0.4 (4)	N1—C1—C2—S1	−4.9 (3)
C14—C15—C16—C17	−175.6 (2)	C3—C2—S1—O1	86.7 (2)
C15—C16—C17—C18	−0.8 (4)	C1—C2—S1—O1	−89.2 (2)
C16—C17—C18—C19	0.0 (4)	C3—C2—S1—O3	−33.1 (2)
C17—C18—C19—C20	1.2 (4)	C1—C2—S1—O3	150.91 (19)
C18—C19—C20—C15	−1.6 (4)	C3—C2—S1—O2	−153.10 (18)
C18—C19—C20—C11	176.9 (2)	C1—C2—S1—O2	31.0 (2)
C16—C15—C20—C19	0.8 (4)	O1—S1—O2—Na1	−18.07 (17)
C14—C15—C20—C19	176.9 (2)	O3—S1—O2—Na1	112.74 (14)
C16—C15—C20—C11	−177.7 (2)	C2—S1—O2—Na1	−133.12 (13)
C14—C15—C20—C11	−1.6 (3)	O1—S1—O3—Na1^i	16.64 (19)
N2—C11—C20—C19	4.5 (3)	O2—S1—O3—Na1^i	−113.75 (15)
C12—C11—C20—C19	−176.1 (2)	C2—S1—O3—Na1^i	130.52 (13)
N2—C11—C20—C15	−177.0 (2)	O1—S1—O3—Na1^iv	−175.20 (12)
C12—C11—C20—C15	2.4 (3)	O2—S1—O3—Na1^iv	54.41 (15)
C20—C11—N2—N1	−179.59 (19)	C2—S1—O3—Na1^iv	−61.32 (13)
C12—C11—N2—N1	1.0 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H61A···O1W^v	0.84 (2)	1.72 (2)	2.549 (3)	169 (4)
N1—H1···O4	0.86 (2)	1.93 (2)	2.615 (3)	136 (3)
N1—H1···O2	0.86 (2)	2.12 (3)	2.747 (3)	129 (3)
O1W—H1WB···O1^iii	0.84 (1)	1.96 (1)	2.761 (3)	158 (3)
O1W—H1WA···O5	0.84 (1)	1.94 (1)	2.748 (3)	159 (3)

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