1,10-Phenanthrolin-1-ium hydrogen d,l-tartrate dihydrate.

In the title hydrated molecular salt, C(12)H(9)N(2) (+)·C(4)H(5)O(6) (-)·2H(2)O, the cation is almost planar (r.m.s. deviation = 0.014 Å); the carbon skeleton of the anion assumes a trans conformation [C-C-C-C torsion angle = -179.86 (14)°]. The carboxyl end of one hydrogen tartrate anion forms a short hydrogen bond to the carboxyl-ate end of another anion [O⋯O = 2.508 (2) Å] in a head-to-tail manner, forming a chain; the chains and water mol-ecules inter-act, generating an O-H⋯O hydrogen-bonded layer. The cation binds to the layer by an N-H⋯O hydrogen bond.

Related literature

For the trihydrated 1,10-phenanthrolin-1-ium salts of d- and l-tartaric acid, see: Derikvand & Olmstead (2010 ▶); Wang et al. (2006 ▶).

Experimental

Crystal data

C12H9N2 +·C4H5O6 −·2H2O

M = 366.32

Triclinic,

a = 7.0933 (7) Å

b = 10.5849 (11) Å

c = 11.4694 (11) Å

α = 98.081 (1)°

β = 100.350 (1)°

γ = 103.903 (1)°

V = 806.95 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.40 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

7610 measured reflections

3635 independent reflections

2880 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.160

S = 1.04

3635 reflections

267 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015972/bt5536sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015972/bt5536Isup2.hkl

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

C12H9N2+·C4H5O6−·2H2O	Z = 2
Mr = 366.32	F(000) = 384
Triclinic, P1	Dx = 1.508 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0933 (7) Å	Cell parameters from 2722 reflections
b = 10.5849 (11) Å	θ = 2.5–28.2°
c = 11.4694 (11) Å	µ = 0.12 mm−1
α = 98.081 (1)°	T = 100 K
β = 100.350 (1)°	Prism, colorless
γ = 103.903 (1)°	0.40 × 0.10 × 0.10 mm
V = 806.95 (14) Å3

Bruker SMART APEX diffractometer	2880 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 27.5°, θmin = 1.8°
ω scans	h = −9→9
7610 measured reflections	k = −13→13
3635 independent reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.1012P)2 + 0.1854P] where P = (Fo2 + 2Fc2)/3
3635 reflections	(Δ/σ)max = 0.001
267 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.0272 (2)	0.97612 (14)	0.33939 (12)	0.0172 (3)
O2	0.00294 (19)	1.04199 (14)	0.16223 (12)	0.0167 (3)
O3	0.3922 (2)	0.95680 (14)	0.34847 (12)	0.0163 (3)
O4	0.1832 (2)	0.78094 (13)	0.12086 (12)	0.0154 (3)
O5	0.6410 (2)	1.02428 (13)	0.15147 (12)	0.0153 (3)
O6	0.5609 (2)	0.80301 (14)	0.09605 (13)	0.0192 (3)
O1W	0.2228 (2)	0.90933 (13)	0.55174 (12)	0.0145 (3)
O2W	0.1595 (2)	1.23818 (15)	0.04324 (13)	0.0174 (3)
N1	0.2289 (2)	0.65380 (16)	0.46822 (15)	0.0143 (3)
N2	0.2713 (2)	0.66417 (16)	0.71074 (15)	0.0171 (4)
C1	0.0952 (3)	1.00580 (17)	0.25142 (16)	0.0125 (4)
C2	0.3085 (3)	1.00188 (18)	0.24666 (16)	0.0124 (4)
H2A	0.3902	1.0934	0.2475	0.015*
C3	0.3050 (3)	0.91028 (18)	0.12952 (16)	0.0115 (4)
H3A	0.2505	0.9473	0.0594	0.014*
C4	0.5161 (3)	0.90552 (18)	0.12418 (16)	0.0122 (4)
C5	0.2130 (3)	0.6578 (2)	0.35202 (18)	0.0184 (4)
H5A	0.2027	0.7366	0.3240	0.022*
C6	0.2114 (3)	0.5459 (2)	0.27087 (19)	0.0220 (5)
H6	0.2015	0.5487	0.1876	0.026*
C7	0.2243 (3)	0.4319 (2)	0.31181 (19)	0.0213 (4)
H7	0.2216	0.3552	0.2567	0.026*
C8	0.2417 (3)	0.42852 (19)	0.43589 (19)	0.0178 (4)
C9	0.2446 (3)	0.54419 (18)	0.51418 (17)	0.0138 (4)
C10	0.2550 (3)	0.3129 (2)	0.4856 (2)	0.0220 (5)
H10	0.2530	0.2340	0.4337	0.026*
C11	0.2704 (3)	0.3145 (2)	0.6049 (2)	0.0224 (5)
H11A	0.2778	0.2366	0.6356	0.027*
C12	0.2757 (3)	0.43249 (19)	0.68601 (19)	0.0173 (4)
C13	0.2645 (3)	0.54791 (18)	0.64134 (18)	0.0149 (4)
C14	0.2935 (3)	0.4390 (2)	0.8110 (2)	0.0227 (5)
H14	0.3004	0.3633	0.8456	0.027*
C15	0.3006 (3)	0.5558 (2)	0.8818 (2)	0.0236 (5)
H15	0.3135	0.5626	0.9665	0.028*
C16	0.2888 (3)	0.6661 (2)	0.82806 (18)	0.0210 (4)
H16	0.2936	0.7464	0.8787	0.025*
H3	0.517 (5)	1.006 (3)	0.381 (3)	0.048 (9)*
H4	0.066 (4)	0.767 (3)	0.067 (3)	0.032 (7)*
H5	0.781 (5)	1.020 (3)	0.156 (3)	0.057 (10)*
H11	0.145 (5)	0.944 (4)	0.593 (4)	0.067 (11)*
H12	0.195 (4)	0.938 (3)	0.480 (3)	0.039 (8)*
H21	0.120 (5)	1.172 (4)	0.074 (3)	0.052 (10)*
H22	0.247 (5)	1.223 (3)	0.003 (3)	0.037 (8)*
H1	0.233 (5)	0.731 (3)	0.520 (3)	0.046 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0162 (7)	0.0231 (7)	0.0161 (7)	0.0078 (6)	0.0087 (5)	0.0054 (5)
O2	0.0131 (7)	0.0224 (7)	0.0178 (7)	0.0070 (5)	0.0060 (5)	0.0070 (6)
O3	0.0120 (7)	0.0243 (7)	0.0118 (7)	0.0032 (6)	0.0015 (5)	0.0055 (5)
O4	0.0139 (7)	0.0137 (7)	0.0165 (7)	0.0017 (5)	0.0018 (5)	0.0020 (5)
O5	0.0123 (7)	0.0156 (7)	0.0197 (7)	0.0047 (5)	0.0058 (5)	0.0036 (5)
O6	0.0187 (7)	0.0173 (7)	0.0250 (8)	0.0097 (6)	0.0070 (6)	0.0042 (6)
O1W	0.0160 (7)	0.0181 (7)	0.0111 (7)	0.0070 (5)	0.0038 (5)	0.0037 (5)
O2W	0.0167 (7)	0.0191 (7)	0.0168 (7)	0.0047 (6)	0.0053 (6)	0.0034 (6)
N1	0.0141 (8)	0.0146 (8)	0.0132 (8)	0.0028 (6)	0.0023 (6)	0.0017 (6)
N2	0.0195 (8)	0.0153 (8)	0.0154 (8)	0.0040 (6)	0.0017 (7)	0.0033 (6)
C1	0.0139 (9)	0.0108 (8)	0.0123 (9)	0.0027 (7)	0.0044 (7)	−0.0003 (7)
C2	0.0105 (8)	0.0153 (9)	0.0120 (9)	0.0034 (7)	0.0039 (7)	0.0027 (7)
C3	0.0115 (8)	0.0142 (8)	0.0101 (8)	0.0042 (7)	0.0035 (7)	0.0041 (7)
C4	0.0146 (9)	0.0153 (8)	0.0083 (8)	0.0053 (7)	0.0036 (7)	0.0041 (7)
C5	0.0159 (9)	0.0225 (10)	0.0166 (10)	0.0039 (8)	0.0040 (7)	0.0051 (8)
C6	0.0196 (10)	0.0278 (11)	0.0169 (10)	0.0038 (8)	0.0059 (8)	0.0009 (8)
C7	0.0148 (9)	0.0226 (10)	0.0229 (11)	0.0041 (8)	0.0051 (8)	−0.0062 (8)
C8	0.0110 (9)	0.0167 (9)	0.0230 (10)	0.0016 (7)	0.0039 (7)	−0.0015 (8)
C9	0.0107 (8)	0.0125 (8)	0.0178 (10)	0.0037 (7)	0.0020 (7)	0.0015 (7)
C10	0.0184 (10)	0.0128 (9)	0.0330 (12)	0.0042 (8)	0.0063 (9)	−0.0019 (8)
C11	0.0201 (10)	0.0122 (9)	0.0354 (12)	0.0058 (8)	0.0042 (9)	0.0065 (8)
C12	0.0131 (9)	0.0145 (9)	0.0239 (11)	0.0038 (7)	0.0020 (8)	0.0050 (8)
C13	0.0113 (8)	0.0134 (9)	0.0189 (10)	0.0029 (7)	0.0016 (7)	0.0031 (7)
C14	0.0227 (10)	0.0194 (10)	0.0282 (11)	0.0068 (8)	0.0026 (9)	0.0137 (9)
C15	0.0270 (11)	0.0248 (11)	0.0188 (10)	0.0056 (9)	0.0016 (8)	0.0105 (8)
C16	0.0262 (11)	0.0180 (10)	0.0164 (10)	0.0047 (8)	0.0016 (8)	0.0017 (8)

O1—C1	1.241 (2)	C3—H3A	1.0000
O2—C1	1.269 (2)	C5—C6	1.395 (3)
O3—C2	1.410 (2)	C5—H5A	0.9500
O3—H3	0.89 (3)	C6—C7	1.372 (3)
O4—C3	1.412 (2)	C6—H6	0.9500
O4—H4	0.91 (3)	C7—C8	1.412 (3)
O5—C4	1.311 (2)	C7—H7	0.9500
O5—H5	1.00 (3)	C8—C9	1.406 (3)
O6—C4	1.219 (2)	C8—C10	1.437 (3)
O1W—H11	0.90 (4)	C9—C13	1.434 (3)
O1W—H12	0.92 (3)	C10—C11	1.350 (3)
O2W—H21	0.84 (4)	C10—H10	0.9500
O2W—H22	0.87 (3)	C11—C12	1.437 (3)
N1—C5	1.325 (3)	C11—H11A	0.9500
N1—C9	1.360 (3)	C12—C13	1.403 (3)
N1—H1	0.93 (3)	C12—C14	1.407 (3)
N2—C16	1.326 (3)	C14—C15	1.365 (3)
N2—C13	1.354 (2)	C14—H14	0.9500
C1—C2	1.534 (2)	C15—C16	1.407 (3)
C2—C3	1.535 (2)	C15—H15	0.9500
C2—H2A	1.0000	C16—H16	0.9500
C3—C4	1.522 (2)
C2—O3—H3	111 (2)	C5—C6—H6	120.1
C3—O4—H4	110.2 (17)	C6—C7—C8	119.99 (19)
C4—O5—H5	111.6 (19)	C6—C7—H7	120.0
H11—O1W—H12	101 (3)	C8—C7—H7	120.0
H21—O2W—H22	109 (3)	C9—C8—C7	118.09 (19)
C5—N1—C9	122.93 (18)	C9—C8—C10	118.62 (19)
C5—N1—H1	117.6 (19)	C7—C8—C10	123.30 (19)
C9—N1—H1	119.4 (19)	N1—C9—C8	119.30 (18)
C16—N2—C13	116.48 (17)	N1—C9—C13	119.82 (17)
O1—C1—O2	125.36 (18)	C8—C9—C13	120.88 (18)
O1—C1—C2	119.50 (17)	C11—C10—C8	121.05 (19)
O2—C1—C2	115.13 (16)	C11—C10—H10	119.5
O3—C2—C1	109.60 (14)	C8—C10—H10	119.5
O3—C2—C3	110.78 (15)	C10—C11—C12	120.86 (19)
C1—C2—C3	109.30 (14)	C10—C11—H11A	119.6
O3—C2—H2A	109.0	C12—C11—H11A	119.6
C1—C2—H2A	109.0	C13—C12—C14	117.29 (18)
C3—C2—H2A	109.0	C13—C12—C11	119.93 (19)
O4—C3—C4	109.91 (14)	C14—C12—C11	122.78 (18)
O4—C3—C2	111.42 (14)	N2—C13—C12	124.24 (18)
C4—C3—C2	109.66 (14)	N2—C13—C9	117.11 (17)
O4—C3—H3A	108.6	C12—C13—C9	118.65 (18)
C4—C3—H3A	108.6	C15—C14—C12	118.92 (19)
C2—C3—H3A	108.6	C15—C14—H14	120.5
O6—C4—O5	124.72 (17)	C12—C14—H14	120.5
O6—C4—C3	123.46 (17)	C14—C15—C16	119.4 (2)
O5—C4—C3	111.81 (15)	C14—C15—H15	120.3
N1—C5—C6	119.94 (19)	C16—C15—H15	120.3
N1—C5—H5A	120.0	N2—C16—C15	123.7 (2)
C6—C5—H5A	120.0	N2—C16—H16	118.1
C7—C6—C5	119.74 (19)	C15—C16—H16	118.1
C7—C6—H6	120.1
O1—C1—C2—O3	2.5 (2)	C10—C8—C9—C13	1.3 (3)
O2—C1—C2—O3	−178.33 (15)	C9—C8—C10—C11	−0.1 (3)
O1—C1—C2—C3	124.08 (18)	C7—C8—C10—C11	−179.65 (19)
O2—C1—C2—C3	−56.7 (2)	C8—C10—C11—C12	−0.6 (3)
O3—C2—C3—O4	62.92 (19)	C10—C11—C12—C13	0.1 (3)
C1—C2—C3—O4	−57.94 (19)	C10—C11—C12—C14	−179.4 (2)
O3—C2—C3—C4	−58.99 (19)	C16—N2—C13—C12	−0.3 (3)
C1—C2—C3—C4	−179.86 (14)	C16—N2—C13—C9	179.70 (17)
O4—C3—C4—O6	11.4 (2)	C14—C12—C13—N2	0.6 (3)
C2—C3—C4—O6	134.17 (19)	C11—C12—C13—N2	−178.96 (18)
O4—C3—C4—O5	−169.64 (14)	C14—C12—C13—C9	−179.49 (17)
C2—C3—C4—O5	−46.8 (2)	C11—C12—C13—C9	1.0 (3)
C9—N1—C5—C6	0.1 (3)	N1—C9—C13—N2	−1.5 (3)
N1—C5—C6—C7	0.7 (3)	C8—C9—C13—N2	178.28 (17)
C5—C6—C7—C8	−0.8 (3)	N1—C9—C13—C12	178.54 (17)
C6—C7—C8—C9	0.2 (3)	C8—C9—C13—C12	−1.7 (3)
C6—C7—C8—C10	179.72 (19)	C13—C12—C14—C15	−0.6 (3)
C5—N1—C9—C8	−0.8 (3)	C11—C12—C14—C15	178.92 (19)
C5—N1—C9—C13	179.01 (18)	C12—C14—C15—C16	0.4 (3)
C7—C8—C9—N1	0.6 (3)	C13—N2—C16—C15	0.1 (3)
C10—C8—C9—N1	−178.97 (17)	C14—C15—C16—N2	−0.2 (3)
C7—C8—C9—C13	−179.19 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1wi	0.89 (3)	1.82 (3)	2.709 (2)	175 (3)
O4—H4···O2wii	0.90 (3)	1.84 (3)	2.739 (2)	172 (3)
O5—H5···O2iii	0.99 (3)	1.52 (3)	2.508 (2)	169 (3)
O1w—H12···O1	0.93 (3)	1.97 (3)	2.846 (2)	157 (3)
O1w—H11···O1iv	0.90 (4)	1.86 (4)	2.753 (2)	173 (4)
O2w—H21···O2	0.84 (4)	1.93 (4)	2.764 (2)	168 (3)
O2w—H22···O6v	0.87 (3)	1.97 (3)	2.835 (2)	176 (3)
N1—H1···O1w	0.93 (3)	1.89 (3)	2.753 (2)	153 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1wi	0.89 (3)	1.82 (3)	2.709 (2)	175 (3)
O4—H4⋯O2wii	0.90 (3)	1.84 (3)	2.739 (2)	172 (3)
O5—H5⋯O2iii	0.99 (3)	1.52 (3)	2.508 (2)	169 (3)
O1w—H12⋯O1	0.93 (3)	1.97 (3)	2.846 (2)	157 (3)
O1w—H11⋯O1iv	0.90 (4)	1.86 (4)	2.753 (2)	173 (4)
O2w—H21⋯O2	0.84 (4)	1.93 (4)	2.764 (2)	168 (3)
O2w—H22⋯O6v	0.87 (3)	1.97 (3)	2.835 (2)	176 (3)
N1—H1⋯O1w	0.93 (3)	1.89 (3)	2.753 (2)	153 (3)

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