Synthesis, crystal structure and Hirshfeld surface analysis of sodium bis­(malonato)borate monohydrate

The asymmetric unit of the title salt, Na⁺·C₆H₄BO₈⁻·H₂O, com­prises a five-coordinate sodium cation, a bis­(malonato)borate anion and a water mol­ecule of crystallization.

Computing details

Poly[aqua[µ₄-bis(malonato)borato]sodium]

Crystal data

[Na(C6H4BO8)(H2O)]	F(000) = 520
Mr = 255.91	Dx = 1.806 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.9058 (4) Å	Cell parameters from 9951 reflections
b = 8.2979 (5) Å	θ = 2.8–30.5°
c = 14.6473 (9) Å	µ = 0.21 mm^−1
β = 101.565 (2)°	T = 298 K
V = 941.38 (9) Å^3	Block, colourless
Z = 4	0.35 × 0.27 × 0.27 mm

Data collection

Bruker D8 VENTURE diffractometer with a PHOTON II detector	2494 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
ω and φ scan	θmax = 30.5°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→11
Tmin = 0.917, Tmax = 0.958	k = −11→11
32209 measured reflections	l = −20→20
2864 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: mixed
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0503P)^2 + 0.3262P] where P = (Fo^2 + 2Fc^2)/3
2864 reflections	(Δ/σ)max < 0.001
162 parameters	Δρmax = 0.53 e Å^−3
4 restraints	Δρmin = −0.60 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	0.24488 (7)	0.47538 (7)	0.76584 (4)	0.03728 (15)
B1	0.76757 (17)	0.52073 (15)	0.55156 (9)	0.0271 (2)
C1	0.59169 (15)	0.47853 (15)	0.66789 (9)	0.0294 (2)
C2	0.64385 (17)	0.30481 (15)	0.66658 (9)	0.0331 (3)
H2A	0.551966	0.239128	0.681940	0.040*
H2B	0.745590	0.288268	0.715054	0.040*
C3	0.68228 (16)	0.24605 (14)	0.57587 (9)	0.0309 (2)
C4	1.01449 (13)	0.68524 (13)	0.61701 (7)	0.0235 (2)
C5	0.93606 (17)	0.81205 (14)	0.54883 (9)	0.0340 (3)
H5A	1.028548	0.875823	0.532601	0.041*
H5B	0.867448	0.883229	0.579401	0.041*
C6	0.82428 (16)	0.75128 (16)	0.46059 (9)	0.0331 (3)
O1	0.64336 (12)	0.57513 (11)	0.60743 (7)	0.0337 (2)
O2	0.50736 (14)	0.53111 (13)	0.72169 (8)	0.0451 (3)
O3	0.74511 (13)	0.35276 (11)	0.52435 (7)	0.0358 (2)
O4	0.66050 (17)	0.10738 (13)	0.55087 (9)	0.0518 (3)
O5	0.94362 (11)	0.54098 (10)	0.60778 (6)	0.02768 (18)
O6	1.13921 (12)	0.71217 (11)	0.67822 (6)	0.0329 (2)
O7	0.74022 (12)	0.61563 (12)	0.46608 (6)	0.0366 (2)
O8	0.80823 (17)	0.82359 (17)	0.38773 (8)	0.0577 (3)
O9	0.00848 (15)	0.39690 (13)	0.82757 (8)	0.0448 (3)
H9A	−0.008 (4)	0.443 (3)	0.8765 (14)	0.088 (9)*
H9B	0.019 (4)	0.2983 (16)	0.8397 (19)	0.100 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na1	0.0334 (3)	0.0373 (3)	0.0430 (3)	0.0070 (2)	0.0124 (2)	0.0112 (2)
B1	0.0289 (6)	0.0257 (6)	0.0283 (6)	−0.0034 (4)	0.0090 (5)	−0.0002 (4)
C1	0.0242 (5)	0.0316 (6)	0.0337 (6)	−0.0052 (4)	0.0089 (4)	−0.0065 (4)
C2	0.0401 (6)	0.0291 (6)	0.0316 (6)	−0.0021 (5)	0.0107 (5)	0.0008 (4)
C3	0.0322 (5)	0.0252 (5)	0.0360 (6)	−0.0037 (4)	0.0086 (4)	−0.0039 (4)
C4	0.0255 (4)	0.0238 (5)	0.0219 (4)	0.0022 (4)	0.0062 (4)	0.0025 (4)
C5	0.0391 (6)	0.0234 (5)	0.0355 (6)	−0.0004 (4)	−0.0022 (5)	0.0087 (5)
C6	0.0310 (5)	0.0382 (6)	0.0286 (6)	0.0004 (5)	0.0025 (4)	0.0120 (5)
O1	0.0349 (4)	0.0249 (4)	0.0456 (5)	0.0004 (3)	0.0180 (4)	−0.0013 (4)
O2	0.0423 (5)	0.0478 (6)	0.0527 (6)	−0.0066 (4)	0.0272 (5)	−0.0150 (5)
O3	0.0458 (5)	0.0288 (4)	0.0375 (5)	−0.0077 (4)	0.0198 (4)	−0.0079 (4)
O4	0.0722 (8)	0.0270 (5)	0.0611 (7)	−0.0110 (5)	0.0249 (6)	−0.0122 (5)
O5	0.0295 (4)	0.0236 (4)	0.0292 (4)	−0.0007 (3)	0.0042 (3)	0.0075 (3)
O6	0.0332 (4)	0.0349 (4)	0.0274 (4)	−0.0009 (3)	−0.0016 (3)	0.0013 (3)
O7	0.0369 (4)	0.0411 (5)	0.0282 (4)	−0.0087 (4)	−0.0017 (3)	0.0066 (4)
O8	0.0601 (7)	0.0713 (8)	0.0370 (6)	−0.0081 (6)	−0.0020 (5)	0.0315 (6)
O9	0.0525 (6)	0.0366 (5)	0.0487 (6)	−0.0035 (4)	0.0181 (5)	0.0039 (5)

Geometric parameters (Å, º)

Na1—O9	2.3264 (12)	C2—H2A	0.9700
Na1—O2	2.3402 (11)	C2—H2B	0.9700
Na1—O6^i	2.4032 (10)	C3—O4	1.2094 (16)
Na1—O8^ii	2.4213 (12)	C3—O3	1.3231 (15)
Na1—O6^iii	2.4455 (11)	C4—O6	1.2130 (14)
Na1—O5^i	3.0195 (10)	C4—O5	1.3171 (13)
B1—O3	1.4508 (15)	C4—C5	1.4969 (15)
B1—O7	1.4581 (16)	C5—C6	1.4993 (18)
B1—O1	1.4697 (15)	C5—H5A	0.9700
B1—O5	1.4779 (15)	C5—H5B	0.9700
C1—O2	1.2109 (15)	C6—O8	1.2086 (15)
C1—O1	1.3186 (15)	C6—O7	1.3177 (16)
C1—C2	1.5005 (17)	O9—H9A	0.846 (13)
C2—C3	1.5024 (17)	O9—H9B	0.838 (13)
O9—Na1—O2	171.38 (5)	O4—C3—C2	122.33 (12)
O9—Na1—O6^i	102.48 (4)	O3—C3—C2	116.93 (10)
O2—Na1—O6^i	85.61 (4)	O6—C4—O5	120.62 (10)
O9—Na1—O8^ii	88.27 (5)	O6—C4—C5	122.02 (10)
O2—Na1—O8^ii	90.22 (5)	O5—C4—C5	117.36 (10)
O6^i—Na1—O8^ii	80.15 (4)	O6—C4—Na1^iv	45.91 (6)
O9—Na1—O6^iii	84.03 (4)	O5—C4—Na1^iv	74.82 (6)
O2—Na1—O6^iii	88.60 (4)	C5—C4—Na1^iv	167.29 (8)
O6^i—Na1—O6^iii	167.40 (3)	C4—C5—C6	115.62 (10)
O8^ii—Na1—O6^iii	111.10 (5)	C4—C5—H5A	108.4
O9—Na1—O5^i	77.10 (4)	C6—C5—H5A	108.4
O2—Na1—O5^i	111.06 (4)	C4—C5—H5B	108.4
O6^i—Na1—O5^i	46.12 (3)	C6—C5—H5B	108.4
O8^ii—Na1—O5^i	117.12 (4)	H5A—C5—H5B	107.4
O6^iii—Na1—O5^i	127.08 (4)	O8—C6—O7	120.86 (13)
O3—B1—O7	107.10 (10)	O8—C6—C5	122.25 (13)
O3—B1—O1	112.92 (9)	O7—C6—C5	116.88 (10)
O7—B1—O1	108.16 (10)	C1—O1—B1	121.25 (10)
O3—B1—O5	108.18 (10)	C1—O2—Na1	137.99 (9)
O7—B1—O5	112.21 (9)	C3—O3—B1	121.70 (10)
O1—B1—O5	108.33 (10)	C4—O5—B1	119.62 (9)
O2—C1—O1	120.21 (12)	C4—O5—Na1^iv	80.28 (6)
O2—C1—C2	122.89 (12)	B1—O5—Na1^iv	156.45 (7)
O1—C1—C2	116.90 (10)	C4—O6—Na1^iv	112.84 (8)
C1—C2—C3	115.33 (11)	C4—O6—Na1^v	127.34 (8)
C1—C2—H2A	108.4	Na1^iv—O6—Na1^v	118.98 (3)
C3—C2—H2A	108.4	C6—O7—B1	121.60 (10)
C1—C2—H2B	108.4	C6—O8—Na1^vi	164.30 (13)
C3—C2—H2B	108.4	Na1—O9—H9A	118 (2)
H2A—C2—H2B	107.5	Na1—O9—H9B	108 (2)
O4—C3—O3	120.73 (12)	H9A—O9—H9B	107 (2)
O2—C1—C2—C3	156.38 (13)	C5—C4—O5—B1	−17.36 (15)
O1—C1—C2—C3	−24.22 (16)	Na1^iv—C4—O5—B1	166.54 (9)
C1—C2—C3—O4	−150.74 (13)	O6—C4—O5—Na1^iv	−3.33 (10)
C1—C2—C3—O3	30.58 (17)	C5—C4—O5—Na1^iv	176.10 (10)
O6—C4—C5—C6	160.61 (11)	O3—B1—O5—C4	159.43 (9)
O5—C4—C5—C6	−18.81 (16)	O7—B1—O5—C4	41.49 (14)
Na1^iv—C4—C5—C6	143.8 (3)	O1—B1—O5—C4	−77.85 (12)
C4—C5—C6—O8	−150.46 (14)	O3—B1—O5—Na1^iv	−55.6 (2)
C4—C5—C6—O7	30.90 (17)	O7—B1—O5—Na1^iv	−173.55 (12)
O2—C1—O1—B1	170.39 (12)	O1—B1—O5—Na1^iv	67.1 (2)
C2—C1—O1—B1	−9.02 (16)	O5—C4—O6—Na1^iv	4.47 (13)
O3—B1—O1—C1	35.76 (16)	C5—C4—O6—Na1^iv	−174.93 (9)
O7—B1—O1—C1	154.11 (10)	O5—C4—O6—Na1^v	−164.81 (7)
O5—B1—O1—C1	−84.03 (13)	C5—C4—O6—Na1^v	15.79 (16)
O1—C1—O2—Na1	126.39 (13)	Na1^iv—C4—O6—Na1^v	−169.29 (12)
C2—C1—O2—Na1	−54.2 (2)	O8—C6—O7—B1	175.44 (14)
O4—C3—O3—B1	178.15 (13)	C5—C6—O7—B1	−5.90 (18)
C2—C3—O3—B1	−3.14 (18)	O3—B1—O7—C6	−147.33 (11)
O7—B1—O3—C3	−147.88 (11)	O1—B1—O7—C6	90.69 (14)
O1—B1—O3—C3	−28.92 (17)	O5—B1—O7—C6	−28.75 (16)
O5—B1—O3—C3	90.96 (13)	O7—C6—O8—Na1^vi	117.5 (4)
O6—C4—O5—B1	163.22 (10)	C5—C6—O8—Na1^vi	−61.0 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O9^iv	0.97	2.54	3.4247 (18)	151
C5—H5B···O4^vii	0.97	2.46	3.2830 (18)	143
O9—H9A···O4^viii	0.85 (1)	2.23 (2)	2.9932 (17)	151 (3)
O9—H9B···O1^ix	0.84 (1)	2.46 (2)	3.1520 (14)	140 (3)
O9—H9B···O2^ix	0.84 (1)	2.39 (2)	3.1166 (17)	146 (3)

Symmetry codes: (iv) x+1, y, z; (vii) x, y+1, z; (viii) −x+1/2, y+1/2, −z+3/2; (ix) −x+1/2, y−1/2, −z+3/2.