Dimethyl-ammonium bis-(3-oxidonaphthalene-2-carboxyl-ato)borate hemihydrate.

The title compound, C(2)H(8)N(+)·C(22)H(12)BO(6) (-)·0.5H(2)O, was synthesized under atmospheric conditions in the presence of dimethyl-formamide acting as a template. The structure is composed of [NH(2)(CH(3))(2)](+) cations, bis-(3-oxidonaphthalene-2-carboxyl-ato)borate anions and water mol-ecules. The water molecule lies on a twofold rotation axis. The stabilization of the crystal structure comes from electrostatic inter-actions and is assisted by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds between the layers.

Related literature

For related literature, see: Carr et al. (2005 ▶); Downard et al. (2002 ▶); Errington et al. (1999 ▶); Green et al. (2000 ▶); Grice et al. (1999 ▶); Li & Liu (2006 ▶); Schubert et al. (2000 ▶); Tombul et al. (2003 ▶); Tombul, Guven, Büyükgüngör et al. (2007 ▶); Touboul et al. (2003 ▶); Zhang & Liu (2006 ▶); Zhang et al. (2005 ▶).

Experimental

Crystal data

C2H8N+·C22H12BO6 −·0.5H2O

M = 438.24

Monoclinic,

a = 32.011 (3) Å

b = 9.774 (1) Å

c = 14.742 (1) Å

β = 112.628 (7)°

V = 4257.2 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 303 (2) K

0.48 × 0.08 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: numerical [using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995 ▶)] T min = 0.981, T max = 0.994

16173 measured reflections

4321 independent reflections

1708 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.093

wR(F 2) = 0.152

S = 1.12

4321 reflections

299 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066810/at2517sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066810/at2517Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C2H8N+·C22H12BO6–·0.5H2O	F000 = 1832
Mr = 438.24	Dx = 1.367 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2075 reflections
a = 32.011 (3) Å	θ = 2.5–21.1º
b = 9.774 (1) Å	µ = 0.10 mm−1
c = 14.742 (1) Å	T = 303 (2) K
β = 112.628 (7)º	Rod shape, light yellow
V = 4257.2 (7) Å3	0.48 × 0.08 × 0.08 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4321 independent reflections
Radiation source: fine-focus sealed tube	1708 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.079
Detector resolution: 8.4012 pixels mm-1	θmax = 26.4º
T = 303(2) K	θmin = 2.5º
Rotation method data acquisition using ω and φ scans	h = −40→40
Absorption correction: numerical[absorption correction using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995)]	k = −9→12
Tmin = 0.981, Tmax = 0.994	l = −18→18
16173 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.093	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0247P)2 + 7.7951P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
4321 reflections	Δρmax = 0.21 e Å−3
299 parameters	Δρmin = −0.23 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	−0.01987 (8)	0.4067 (3)	0.37753 (18)	0.0487 (8)
O2	−0.03911 (9)	0.2873 (3)	0.5007 (2)	0.0520 (8)
O3	0.01354 (9)	0.2159 (3)	0.6392 (2)	0.0643 (9)
O4	−0.09425 (8)	0.4084 (3)	0.37123 (19)	0.0474 (7)
O5	−0.06167 (9)	0.2000 (3)	0.33692 (19)	0.0498 (8)
O6	−0.10420 (9)	0.0190 (3)	0.2734 (2)	0.0608 (9)
C1	0.02357 (13)	0.3624 (4)	0.4222 (3)	0.0421 (11)
C2	0.05411 (13)	0.3882 (4)	0.3807 (3)	0.0443 (11)
H2	0.0451	0.4358	0.3216	0.053*
C3	0.09922 (13)	0.3435 (4)	0.4264 (3)	0.0423 (11)
C4	0.13136 (14)	0.3649 (5)	0.3838 (3)	0.0564 (13)
H4	0.1230	0.4126	0.3249	0.068*
C5	0.17420 (16)	0.3169 (5)	0.4274 (4)	0.0693 (15)
H5	0.1947	0.3314	0.3976	0.083*
C6	0.18799 (15)	0.2461 (5)	0.5163 (4)	0.0712 (15)
H6	0.2175	0.2135	0.5452	0.085*
C7	0.15843 (14)	0.2246 (5)	0.5608 (3)	0.0615 (13)
H7	0.1679	0.1784	0.6205	0.074*
C8	0.11340 (13)	0.2721 (4)	0.5170 (3)	0.0443 (11)
C9	0.08061 (13)	0.2483 (4)	0.5579 (3)	0.0457 (11)
H9	0.0890	0.2026	0.6176	0.055*
C10	0.03693 (13)	0.2910 (4)	0.5115 (3)	0.0398 (10)
C11	0.00351 (14)	0.2617 (4)	0.5560 (4)	0.0482 (12)
C12	−0.13259 (13)	0.3378 (4)	0.3605 (3)	0.0406 (10)
C13	−0.16686 (12)	0.4009 (4)	0.3771 (3)	0.0462 (11)
H13	−0.1638	0.4923	0.3962	0.055*
C14	−0.20682 (13)	0.3303 (5)	0.3661 (3)	0.0470 (12)
C15	−0.24235 (14)	0.3923 (5)	0.3855 (3)	0.0686 (15)
H15	−0.2397	0.4828	0.4065	0.082*
C16	−0.28029 (16)	0.3202 (6)	0.3738 (4)	0.0833 (17)
H16	−0.3035	0.3628	0.3863	0.100*
C17	−0.28545 (16)	0.1834 (6)	0.3434 (4)	0.0858 (17)
H17	−0.3117	0.1356	0.3362	0.103*
C18	−0.25178 (14)	0.1214 (5)	0.3245 (3)	0.0694 (14)
H18	−0.2551	0.0304	0.3046	0.083*
C19	−0.21161 (13)	0.1922 (5)	0.3345 (3)	0.0457 (11)
C20	−0.17613 (13)	0.1312 (4)	0.3159 (3)	0.0463 (11)
H20	−0.1792	0.0412	0.2937	0.056*
C21	−0.13709 (12)	0.2008 (4)	0.3295 (3)	0.0379 (10)
C22	−0.10027 (14)	0.1318 (5)	0.3107 (3)	0.0466 (11)
B1	−0.05381 (15)	0.3300 (5)	0.3956 (4)	0.0444 (13)
N5	−0.06832 (10)	0.8557 (4)	0.1613 (2)	0.0518 (9)
H25A	−0.0368	0.8299	0.1688	0.062*
H25B	−0.0619	0.9008	0.2225	0.062*
C23	−0.09329 (15)	0.7284 (5)	0.1570 (4)	0.0791 (16)
H23A	−0.0763	0.6713	0.2117	0.095*
H23B	−0.0979	0.6813	0.0967	0.095*
H23C	−0.1221	0.7494	0.1596	0.095*
C24	−0.09181 (16)	0.9503 (5)	0.0806 (3)	0.0898 (18)
H24A	−0.0997	0.9036	0.0190	0.108*
H24B	−0.0723	1.0261	0.0831	0.108*
H24C	−0.1188	0.9833	0.0869	0.108*
O7	0.0000	0.0715 (4)	0.2500	0.0849 (15)
H27	−0.0156 (12)	0.1236 (14)	0.271 (3)	0.102*

	U11	U22	U33	U12	U13	U23
O1	0.0322 (16)	0.061 (2)	0.0533 (19)	−0.0011 (15)	0.0168 (15)	0.0074 (15)
O2	0.0364 (16)	0.071 (2)	0.053 (2)	−0.0023 (16)	0.0217 (15)	0.0056 (17)
O3	0.0504 (18)	0.088 (3)	0.058 (2)	−0.0010 (17)	0.0247 (17)	0.0188 (19)
O4	0.0370 (16)	0.0427 (19)	0.0651 (19)	−0.0031 (14)	0.0226 (15)	−0.0049 (15)
O5	0.0442 (17)	0.047 (2)	0.063 (2)	0.0006 (15)	0.0262 (16)	−0.0089 (16)
O6	0.0632 (19)	0.051 (2)	0.078 (2)	0.0015 (17)	0.0375 (17)	−0.0150 (18)
C1	0.037 (3)	0.042 (3)	0.048 (3)	−0.006 (2)	0.017 (2)	0.000 (2)
C2	0.040 (3)	0.050 (3)	0.045 (3)	−0.008 (2)	0.020 (2)	0.000 (2)
C3	0.038 (3)	0.043 (3)	0.049 (3)	−0.010 (2)	0.019 (2)	−0.012 (2)
C4	0.046 (3)	0.067 (3)	0.067 (3)	−0.013 (3)	0.033 (3)	−0.011 (3)
C5	0.052 (3)	0.084 (4)	0.088 (4)	−0.009 (3)	0.045 (3)	−0.012 (3)
C6	0.040 (3)	0.076 (4)	0.103 (4)	0.001 (3)	0.033 (3)	0.001 (3)
C7	0.043 (3)	0.060 (3)	0.079 (3)	0.003 (2)	0.020 (3)	0.007 (3)
C8	0.038 (3)	0.042 (3)	0.049 (3)	−0.004 (2)	0.012 (2)	−0.003 (2)
C9	0.046 (3)	0.045 (3)	0.049 (3)	−0.003 (2)	0.021 (2)	0.000 (2)
C10	0.035 (2)	0.040 (3)	0.048 (3)	−0.005 (2)	0.021 (2)	0.001 (2)
C11	0.046 (3)	0.047 (3)	0.056 (3)	−0.004 (2)	0.024 (3)	−0.002 (3)
C12	0.038 (2)	0.038 (3)	0.047 (3)	−0.001 (2)	0.017 (2)	−0.002 (2)
C13	0.040 (2)	0.041 (3)	0.060 (3)	0.001 (2)	0.021 (2)	−0.008 (2)
C14	0.034 (2)	0.054 (3)	0.056 (3)	0.005 (2)	0.020 (2)	−0.003 (2)
C15	0.047 (3)	0.069 (4)	0.100 (4)	0.002 (3)	0.039 (3)	−0.007 (3)
C16	0.054 (3)	0.085 (5)	0.123 (5)	0.004 (3)	0.048 (3)	−0.006 (4)
C17	0.049 (3)	0.086 (5)	0.133 (5)	−0.015 (3)	0.046 (3)	−0.006 (4)
C18	0.053 (3)	0.070 (4)	0.089 (4)	−0.011 (3)	0.031 (3)	−0.004 (3)
C19	0.035 (2)	0.053 (3)	0.050 (3)	−0.003 (2)	0.018 (2)	0.001 (2)
C20	0.048 (3)	0.045 (3)	0.047 (3)	−0.002 (2)	0.019 (2)	−0.005 (2)
C21	0.033 (2)	0.041 (3)	0.040 (3)	0.004 (2)	0.014 (2)	0.001 (2)
C22	0.049 (3)	0.045 (3)	0.048 (3)	0.001 (3)	0.021 (2)	−0.002 (2)
B1	0.027 (3)	0.057 (4)	0.050 (3)	−0.002 (3)	0.017 (3)	0.001 (3)
N5	0.048 (2)	0.056 (2)	0.052 (2)	0.006 (2)	0.0200 (19)	−0.003 (2)
C23	0.069 (3)	0.074 (4)	0.097 (4)	−0.020 (3)	0.035 (3)	−0.026 (3)
C24	0.106 (4)	0.096 (5)	0.065 (4)	0.040 (4)	0.029 (3)	0.013 (3)
O7	0.086 (4)	0.060 (3)	0.135 (4)	0.000	0.071 (3)	0.000

O1—C1	1.360 (4)	C12—C21	1.405 (5)
O1—B1	1.427 (5)	C13—C14	1.406 (5)
O2—C11	1.316 (4)	C13—H13	0.9300
O2—B1	1.496 (5)	C14—C15	1.412 (5)
O3—C11	1.227 (4)	C14—C19	1.417 (5)
O4—C12	1.363 (4)	C15—C16	1.356 (6)
O4—B1	1.426 (5)	C15—H15	0.9300
O5—C22	1.324 (4)	C16—C17	1.399 (6)
O5—B1	1.502 (5)	C16—H16	0.9300
O6—C22	1.216 (4)	C17—C18	1.355 (6)
C1—C2	1.362 (5)	C17—H17	0.9300
C1—C10	1.404 (5)	C18—C19	1.417 (5)
C2—C3	1.408 (5)	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.400 (5)
C3—C4	1.412 (5)	C20—C21	1.368 (5)
C3—C8	1.417 (5)	C20—H20	0.9300
C4—C5	1.355 (6)	C21—C22	1.473 (5)
C4—H4	0.9300	N5—C24	1.466 (5)
C5—C6	1.395 (6)	N5—C23	1.467 (5)
C5—H5	0.9300	N5—H25A	1.0035
C6—C7	1.360 (5)	N5—H25B	0.9530
C6—H6	0.9300	C23—H23A	0.9600
C7—C8	1.412 (5)	C23—H23B	0.9600
C7—H7	0.9300	C23—H23C	0.9600
C8—C9	1.416 (5)	C24—H24A	0.9600
C9—C10	1.364 (5)	C24—H24B	0.9600
C9—H9	0.9300	C24—H24C	0.9600
C10—C11	1.482 (5)	O7—H27	0.85 (3)
C12—C13	1.361 (5)
C1—O1—B1	116.9 (3)	C16—C15—H15	119.9
C11—O2—B1	122.2 (3)	C14—C15—H15	119.9
C12—O4—B1	116.5 (3)	C15—C16—C17	121.8 (5)
C22—O5—B1	121.6 (3)	C15—C16—H16	119.1
O1—C1—C2	120.0 (4)	C17—C16—H16	119.1
O1—C1—C10	119.9 (4)	C18—C17—C16	119.2 (5)
C2—C1—C10	120.1 (4)	C18—C17—H17	120.4
C1—C2—C3	120.5 (4)	C16—C17—H17	120.4
C1—C2—H2	119.7	C17—C18—C19	121.4 (5)
C3—C2—H2	119.7	C17—C18—H18	119.3
C2—C3—C4	121.9 (4)	C19—C18—H18	119.3
C2—C3—C8	120.2 (4)	C20—C19—C18	122.9 (4)
C4—C3—C8	117.9 (4)	C20—C19—C14	118.5 (4)
C5—C4—C3	121.0 (5)	C18—C19—C14	118.6 (4)
C5—C4—H4	119.5	C21—C20—C19	121.6 (4)
C3—C4—H4	119.5	C21—C20—H20	119.2
C4—C5—C6	120.9 (4)	C19—C20—H20	119.2
C4—C5—H5	119.5	C20—C21—C12	119.7 (4)
C6—C5—H5	119.5	C20—C21—C22	119.8 (4)
C7—C6—C5	120.2 (4)	C12—C21—C22	120.5 (4)
C7—C6—H6	119.9	O6—C22—O5	120.7 (4)
C5—C6—H6	119.9	O6—C22—C21	123.3 (4)
C6—C7—C8	120.4 (5)	O5—C22—C21	116.0 (4)
C6—C7—H7	119.8	O4—B1—O1	110.7 (4)
C8—C7—H7	119.8	O4—B1—O2	107.7 (3)
C7—C8—C9	123.0 (4)	O1—B1—O2	112.4 (3)
C7—C8—C3	119.6 (4)	O4—B1—O5	112.0 (3)
C9—C8—C3	117.4 (4)	O1—B1—O5	107.9 (3)
C10—C9—C8	121.4 (4)	O2—B1—O5	106.1 (4)
C10—C9—H9	119.3	C24—N5—C23	113.5 (4)
C8—C9—H9	119.3	C24—N5—H25A	115.4
C9—C10—C1	120.4 (4)	C23—N5—H25A	107.4
C9—C10—C11	119.6 (4)	C24—N5—H25B	109.4
C1—C10—C11	120.0 (4)	C23—N5—H25B	110.4
O3—C11—O2	119.9 (4)	H25A—N5—H25B	99.9
O3—C11—C10	123.9 (4)	N5—C23—H23A	109.5
O2—C11—C10	116.2 (4)	N5—C23—H23B	109.5
C13—C12—O4	120.1 (4)	H23A—C23—H23B	109.5
C13—C12—C21	120.1 (4)	N5—C23—H23C	109.5
O4—C12—C21	119.7 (4)	H23A—C23—H23C	109.5
C12—C13—C14	121.2 (4)	H23B—C23—H23C	109.5
C12—C13—H13	119.4	N5—C24—H24A	109.5
C14—C13—H13	119.4	N5—C24—H24B	109.5
C13—C14—C15	122.3 (4)	H24A—C24—H24B	109.5
C13—C14—C19	118.9 (4)	N5—C24—H24C	109.5
C15—C14—C19	118.8 (4)	H24A—C24—H24C	109.5
C16—C15—C14	120.2 (5)	H24B—C24—H24C	109.5
B1—O1—C1—C2	152.4 (4)	C13—C14—C15—C16	180.0 (4)
B1—O1—C1—C10	−28.0 (5)	C19—C14—C15—C16	−0.2 (7)
O1—C1—C2—C3	179.7 (4)	C14—C15—C16—C17	0.6 (8)
C10—C1—C2—C3	0.1 (6)	C15—C16—C17—C18	−0.4 (9)
C1—C2—C3—C4	178.0 (4)	C16—C17—C18—C19	−0.3 (8)
C1—C2—C3—C8	−0.6 (6)	C17—C18—C19—C20	179.8 (5)
C2—C3—C4—C5	−177.7 (4)	C17—C18—C19—C14	0.8 (7)
C8—C3—C4—C5	1.0 (6)	C13—C14—C19—C20	0.2 (6)
C3—C4—C5—C6	−0.7 (7)	C15—C14—C19—C20	−179.6 (4)
C4—C5—C6—C7	−0.2 (8)	C13—C14—C19—C18	179.3 (4)
C5—C6—C7—C8	0.8 (7)	C15—C14—C19—C18	−0.5 (6)
C6—C7—C8—C9	177.5 (4)	C18—C19—C20—C21	−177.6 (4)
C6—C7—C8—C3	−0.5 (6)	C14—C19—C20—C21	1.4 (6)
C2—C3—C8—C7	178.3 (4)	C19—C20—C21—C12	−1.7 (6)
C4—C3—C8—C7	−0.4 (6)	C19—C20—C21—C22	178.9 (4)
C2—C3—C8—C9	0.2 (6)	C13—C12—C21—C20	0.2 (6)
C4—C3—C8—C9	−178.5 (4)	O4—C12—C21—C20	−178.1 (3)
C7—C8—C9—C10	−177.3 (4)	C13—C12—C21—C22	179.6 (4)
C3—C8—C9—C10	0.7 (6)	O4—C12—C21—C22	1.4 (5)
C8—C9—C10—C1	−1.2 (6)	B1—O5—C22—O6	−171.3 (4)
C8—C9—C10—C11	178.9 (4)	B1—O5—C22—C21	8.7 (5)
O1—C1—C10—C9	−178.8 (4)	C20—C21—C22—O6	8.0 (6)
C2—C1—C10—C9	0.8 (6)	C12—C21—C22—O6	−171.4 (4)
O1—C1—C10—C11	1.1 (6)	C20—C21—C22—O5	−172.0 (4)
C2—C1—C10—C11	−179.3 (4)	C12—C21—C22—O5	8.5 (5)
B1—O2—C11—O3	−173.9 (4)	C12—O4—B1—O1	163.5 (3)
B1—O2—C11—C10	6.0 (6)	C12—O4—B1—O2	−73.2 (4)
C9—C10—C11—O3	9.7 (6)	C12—O4—B1—O5	43.1 (5)
C1—C10—C11—O3	−170.2 (4)	C1—O1—B1—O4	161.8 (3)
C9—C10—C11—O2	−170.2 (4)	C1—O1—B1—O2	41.4 (5)
C1—C10—C11—O2	9.9 (6)	C1—O1—B1—O5	−75.3 (4)
B1—O4—C12—C13	153.2 (4)	C11—O2—B1—O4	−153.3 (4)
B1—O4—C12—C21	−28.6 (5)	C11—O2—B1—O1	−31.1 (6)
O4—C12—C13—C14	179.7 (4)	C11—O2—B1—O5	86.6 (4)
C21—C12—C13—C14	1.5 (6)	C22—O5—B1—O4	−34.1 (5)
C12—C13—C14—C15	178.2 (4)	C22—O5—B1—O1	−156.1 (3)
C12—C13—C14—C19	−1.7 (6)	C22—O5—B1—O2	83.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H25A···O3i	1.00	1.88	2.849 (4)	162
N5—H25B···O6ii	0.95	2.12	2.839 (4)	131
N5—H25B···O3iii	0.95	2.33	2.871 (4)	116
O7—H27···O5	0.85 (3)	2.18 (4)	3.010 (3)	163.3 (12)

O1—B1	1.427 (5)
O2—B1	1.496 (5)
O4—B1	1.426 (5)
O5—B1	1.502 (5)

O4—B1—O1	110.7 (4)
O4—B1—O2	107.7 (3)
O1—B1—O2	112.4 (3)
O4—B1—O5	112.0 (3)
O1—B1—O5	107.9 (3)
O2—B1—O5	106.1 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H25A⋯O3i	1.00	1.88	2.849 (4)	162
N5—H25B⋯O6ii	0.95	2.12	2.839 (4)	131
N5—H25B⋯O3iii	0.95	2.33	2.871 (4)	116
O7—H27⋯O5	0.85 (3)	2.18 (4)	3.010 (3)	163.3 (12)

Symmetry codes: (i) ; (ii) ; (iii) .