1,10-Phenanthrolin-1-ium hydrogen (S,S)-tartrate trihydrate and a correction.

The title structure, C(12)H(9)N(2) (+)·C(4)H(5)O(6) (-)·3H(2)O, shows that one of the protons of d-tartaric acid has been transferred to 1,10-phenanthroline. The d-hydrogen tartrate anions are joined together in a head-to-tail fashion via a short hydrogen bond with donor-acceptor distance of 2.4554 (12) Å, unsymmetrical O-H distances of 1.01 (4) Å and 1.45 (4) Å, and a 174 (4)° O-H-O bond angle. The phenanthrolinium rings are π-stacked with an average separation of 3.58 (11) Å. The structural report corrects a previous report in the literature [Wang et al. (2006 ▶). Acta Cryst. E62, o2508-o2509] of the isostructural l-hydrogen tartrate enanti-omer in which the proton transfer and short hydrogen bond were missed.

Related literature

For related proton-transfer hydrogen tartrate structures, see: Bai et al. (2005 ▶); Paixão et al. (1999 ▶); Smith et al. (2006 ▶); Su et al. (2009 ▶); Suresh et al. (2006 ▶); Wang et al. (2006 ▶, 2008 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

C12H9N2 +·C4H5O6 −·3H2O

M = 384.34

Orthorhombic,

a = 7.1163 (14) Å

b = 12.482 (3) Å

c = 19.466 (4) Å

V = 1729.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 90 K

0.42 × 0.21 × 0.13 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.880, T max = 0.984

39094 measured reflections

3251 independent reflections

3149 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.06

3251 reflections

324 parameters

All H-atom parameters refined

Δρmax = 0.41 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905332X/nk2019sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905332X/nk2019Isup2.hkl

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

C12H9N2+·C4H5O6−·3H2O	F(000) = 808
Mr = 384.34	Dx = 1.476 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9999 reflections
a = 7.1163 (14) Å	θ = 2.8–31.5°
b = 12.482 (3) Å	µ = 0.12 mm−1
c = 19.466 (4) Å	T = 90 K
V = 1729.2 (6) Å3	Rod, colourless
Z = 4	0.42 × 0.21 × 0.13 mm

Bruker SMART APEXII diffractometer	3251 independent reflections
Radiation source: fine-focus sealed tube	3149 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 8.3 pixels mm-1	θmax = 31.6°, θmin = 1.9°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −18→18
Tmin = 0.880, Tmax = 0.984	l = −28→28
39094 measured reflections

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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F2) = 0.089	All H-atom parameters refined
S = 1.06	w = 1/[σ2(Fo2) + (0.0669P)2 + 0.1713P] where P = (Fo2 + 2Fc2)/3
3251 reflections	(Δ/σ)max = 0.003
324 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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	−0.02434 (15)	0.28085 (14)	0.60625 (5)	0.0387 (3)
O2	−0.01282 (11)	0.22520 (7)	0.71533 (4)	0.01530 (16)
H2A	−0.155 (5)	0.227 (3)	0.7139 (19)	0.082 (11)*
O3	0.34399 (12)	0.27724 (8)	0.59021 (4)	0.01825 (18)
H3A	0.266 (3)	0.2529 (17)	0.5600 (11)	0.025 (5)*
O4	0.29691 (13)	0.43589 (7)	0.69506 (5)	0.01723 (17)
H4A	0.202 (4)	0.450 (2)	0.7164 (15)	0.052 (7)*
O5	0.65945 (13)	0.40940 (7)	0.69497 (5)	0.02051 (18)
O6	0.64269 (11)	0.23538 (7)	0.71823 (4)	0.01439 (15)
N1	0.56039 (18)	0.85195 (8)	0.60703 (5)	0.01821 (19)
N2	0.55402 (17)	0.64831 (8)	0.55452 (5)	0.01820 (19)
H2B	0.558 (3)	0.6546 (15)	0.6011 (10)	0.020 (4)*
C1	0.5526 (2)	0.54779 (10)	0.53258 (7)	0.0244 (3)
H1	0.545 (4)	0.494 (2)	0.5654 (13)	0.038 (6)*
C2	0.5479 (2)	0.52505 (11)	0.46232 (7)	0.0267 (3)
H2	0.545 (4)	0.4546 (18)	0.4486 (12)	0.033 (5)*
C3	0.5443 (2)	0.60764 (12)	0.41615 (7)	0.0238 (2)
H3	0.533 (4)	0.590 (2)	0.3720 (13)	0.042 (6)*
C4	0.54614 (19)	0.71407 (10)	0.43933 (6)	0.0194 (2)
C5	0.5432 (2)	0.80340 (13)	0.39336 (6)	0.0263 (3)
H5	0.533 (5)	0.792 (3)	0.3465 (16)	0.071 (9)*
C6	0.5492 (2)	0.90440 (12)	0.41791 (6)	0.0266 (3)
H6	0.549 (4)	0.966 (2)	0.3898 (14)	0.053 (8)*
C7	0.55687 (19)	0.92492 (10)	0.49056 (6)	0.0190 (2)
C8	0.5681 (2)	1.02891 (10)	0.51766 (7)	0.0217 (2)
H8	0.568 (3)	1.0922 (17)	0.4873 (10)	0.026 (5)*
C9	0.5760 (2)	1.04196 (10)	0.58747 (7)	0.0206 (2)
H9	0.584 (3)	1.1120 (18)	0.6092 (10)	0.029 (5)*
C10	0.5697 (2)	0.95135 (10)	0.63030 (6)	0.0201 (2)
H10	0.577 (3)	0.9670 (17)	0.6820 (11)	0.027 (5)*
C11	0.55581 (17)	0.83917 (9)	0.53766 (5)	0.01526 (19)
C12	0.55133 (17)	0.73284 (9)	0.51062 (6)	0.0157 (2)
C13	0.06195 (15)	0.25433 (10)	0.65712 (5)	0.01487 (19)
C14	0.27564 (14)	0.25118 (9)	0.65602 (5)	0.01263 (18)
H14	0.308 (3)	0.1803 (15)	0.6702 (9)	0.018 (4)*
C15	0.35517 (14)	0.33050 (8)	0.70860 (5)	0.01159 (17)
H15	0.316 (3)	0.3068 (14)	0.7552 (9)	0.017 (4)*
C16	0.57000 (15)	0.32740 (8)	0.70659 (5)	0.01187 (18)
O7	0.57458 (15)	0.62117 (7)	0.68894 (5)	0.01850 (17)
H7A	0.491 (3)	0.6571 (19)	0.7160 (11)	0.034 (6)*
H7B	0.549 (4)	0.558 (2)	0.6918 (12)	0.040 (6)*
O8	−0.31974 (13)	0.30315 (9)	0.52265 (4)	0.02028 (18)
H8A	−0.422 (4)	0.2882 (19)	0.5431 (12)	0.035 (6)*
H8B	−0.231 (4)	0.301 (2)	0.5572 (12)	0.041 (6)*
O9	0.97193 (13)	0.49415 (8)	0.75731 (5)	0.01928 (18)
H9A	0.952 (4)	0.563 (2)	0.7552 (14)	0.047 (7)*
H9B	0.883 (4)	0.4694 (19)	0.7395 (13)	0.038 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0136 (4)	0.0860 (11)	0.0166 (4)	0.0040 (5)	−0.0014 (3)	0.0110 (5)
O2	0.0102 (3)	0.0187 (4)	0.0171 (3)	0.0010 (3)	0.0016 (3)	0.0048 (3)
O3	0.0133 (3)	0.0298 (4)	0.0117 (3)	−0.0028 (3)	0.0021 (3)	−0.0019 (3)
O4	0.0153 (3)	0.0125 (3)	0.0240 (4)	0.0043 (3)	0.0014 (3)	0.0015 (3)
O5	0.0138 (3)	0.0135 (3)	0.0343 (5)	−0.0021 (3)	−0.0009 (3)	0.0033 (3)
O6	0.0097 (3)	0.0125 (3)	0.0209 (4)	0.0009 (3)	0.0011 (3)	0.0031 (3)
N1	0.0262 (5)	0.0151 (4)	0.0134 (4)	0.0032 (4)	0.0004 (4)	−0.0002 (3)
N2	0.0240 (5)	0.0154 (4)	0.0152 (4)	0.0024 (4)	−0.0009 (4)	−0.0013 (3)
C1	0.0332 (7)	0.0167 (5)	0.0234 (6)	0.0027 (5)	−0.0030 (5)	−0.0039 (4)
C2	0.0333 (7)	0.0210 (5)	0.0259 (6)	0.0034 (6)	−0.0050 (5)	−0.0095 (5)
C3	0.0255 (6)	0.0276 (6)	0.0182 (5)	0.0008 (5)	−0.0021 (5)	−0.0092 (4)
C4	0.0208 (5)	0.0238 (5)	0.0138 (4)	−0.0007 (5)	−0.0007 (4)	−0.0037 (4)
C5	0.0347 (7)	0.0318 (6)	0.0124 (4)	−0.0030 (6)	−0.0003 (5)	0.0008 (4)
C6	0.0376 (7)	0.0282 (6)	0.0140 (5)	−0.0036 (6)	−0.0008 (5)	0.0061 (4)
C7	0.0223 (5)	0.0198 (5)	0.0148 (4)	−0.0010 (5)	−0.0004 (4)	0.0041 (4)
C8	0.0266 (6)	0.0173 (5)	0.0214 (5)	0.0009 (5)	0.0001 (5)	0.0052 (4)
C9	0.0262 (5)	0.0139 (4)	0.0217 (5)	0.0034 (5)	0.0011 (5)	0.0016 (4)
C10	0.0292 (6)	0.0153 (4)	0.0158 (4)	0.0038 (5)	0.0011 (4)	−0.0006 (4)
C11	0.0173 (5)	0.0148 (4)	0.0137 (4)	0.0013 (4)	0.0003 (4)	0.0006 (3)
C12	0.0168 (5)	0.0168 (5)	0.0135 (4)	0.0006 (4)	−0.0005 (4)	−0.0012 (4)
C13	0.0097 (4)	0.0206 (5)	0.0143 (4)	−0.0004 (4)	0.0003 (3)	−0.0016 (4)
C14	0.0093 (4)	0.0161 (4)	0.0124 (4)	0.0003 (4)	0.0004 (3)	−0.0015 (3)
C15	0.0098 (4)	0.0116 (4)	0.0134 (4)	0.0011 (3)	−0.0002 (3)	−0.0001 (3)
C16	0.0105 (4)	0.0133 (4)	0.0118 (4)	0.0001 (4)	−0.0001 (3)	−0.0001 (3)
O7	0.0251 (4)	0.0114 (3)	0.0190 (4)	0.0008 (3)	0.0038 (3)	−0.0004 (3)
O8	0.0146 (4)	0.0316 (5)	0.0146 (3)	0.0005 (4)	0.0001 (3)	−0.0010 (3)
O9	0.0173 (4)	0.0166 (4)	0.0240 (4)	0.0006 (3)	−0.0010 (3)	−0.0015 (3)

O1—C13	1.2113 (15)	C5—H5	0.92 (3)
O2—C13	1.3036 (13)	C6—C7	1.4384 (17)
O2—H2A	1.01 (4)	C6—H6	0.95 (3)
O3—C14	1.4082 (13)	C7—C8	1.4034 (18)
O3—H3A	0.86 (2)	C7—C11	1.4094 (16)
O4—C15	1.4043 (13)	C8—C9	1.3696 (18)
O4—H4A	0.81 (3)	C8—H8	0.99 (2)
O5—C16	1.2264 (14)	C9—C10	1.4059 (17)
O6—C16	1.2800 (13)	C9—H9	0.97 (2)
N1—C10	1.3226 (15)	C10—H10	1.03 (2)
N1—C11	1.3602 (14)	C11—C12	1.4282 (16)
N2—C1	1.3254 (16)	C13—C14	1.5214 (15)
N2—C12	1.3579 (15)	C14—C15	1.5324 (15)
N2—H2B	0.912 (19)	C14—H14	0.955 (19)
C1—C2	1.3973 (19)	C15—C16	1.5298 (15)
C1—H1	0.93 (3)	C15—H15	0.994 (17)
C2—C3	1.368 (2)	O7—H7A	0.91 (2)
C2—H2	0.92 (2)	O7—H7B	0.81 (3)
C3—C4	1.4030 (18)	O8—H8A	0.85 (3)
C3—H3	0.89 (3)	O8—H8B	0.92 (3)
C4—C12	1.4079 (15)	O9—H9A	0.87 (3)
C4—C5	1.4299 (19)	O9—H9B	0.79 (3)
C5—C6	1.349 (2)
C13—O2—H2A	112 (2)	C8—C9—H9	122.7 (12)
C14—O3—H3A	108.6 (14)	C10—C9—H9	117.8 (12)
C15—O4—H4A	111 (2)	N1—C10—C9	123.59 (11)
C10—N1—C11	116.83 (10)	N1—C10—H10	121.1 (12)
C1—N2—C12	122.19 (11)	C9—C10—H10	115.2 (12)
C1—N2—H2B	113.7 (12)	N1—C11—C7	123.82 (11)
C12—N2—H2B	124.1 (12)	N1—C11—C12	118.39 (10)
N2—C1—C2	120.52 (12)	C7—C11—C12	117.79 (10)
N2—C1—H1	117.8 (15)	N2—C12—C4	119.43 (11)
C2—C1—H1	121.5 (15)	N2—C12—C11	119.33 (10)
C3—C2—C1	119.37 (12)	C4—C12—C11	121.23 (10)
C3—C2—H2	121.9 (14)	O1—C13—O2	125.45 (11)
C1—C2—H2	118.7 (14)	O1—C13—C14	120.15 (10)
C2—C3—C4	120.14 (11)	O2—C13—C14	114.40 (9)
C2—C3—H3	116.8 (17)	O3—C14—C13	110.62 (9)
C4—C3—H3	122.9 (17)	O3—C14—C15	109.32 (9)
C3—C4—C12	118.35 (11)	C13—C14—C15	110.06 (9)
C3—C4—C5	122.48 (11)	O3—C14—H14	113.3 (11)
C12—C4—C5	119.17 (12)	C13—C14—H14	105.1 (13)
C6—C5—C4	120.45 (11)	C15—C14—H14	108.4 (12)
C6—C5—H5	119 (2)	O4—C15—C16	108.30 (9)
C4—C5—H5	120 (2)	O4—C15—C14	111.77 (9)
C5—C6—C7	121.07 (12)	C16—C15—C14	109.61 (9)
C5—C6—H6	123.9 (16)	O4—C15—H15	111.5 (11)
C7—C6—H6	115.1 (16)	C16—C15—H15	107.4 (11)
C8—C7—C11	117.27 (11)	C14—C15—H15	108.2 (11)
C8—C7—C6	122.45 (11)	O5—C16—O6	124.88 (10)
C11—C7—C6	120.27 (12)	O5—C16—C15	120.16 (10)
C9—C8—C7	119.03 (11)	O6—C16—C15	114.96 (9)
C9—C8—H8	120.0 (12)	H7A—O7—H7B	107 (2)
C7—C8—H8	121.0 (12)	H8A—O8—H8B	104 (2)
C8—C9—C10	119.43 (11)	H9A—O9—H9B	104 (3)
C12—N2—C1—C2	−0.1 (2)	C1—N2—C12—C11	−179.10 (13)
N2—C1—C2—C3	−0.2 (3)	C3—C4—C12—N2	−0.10 (19)
C1—C2—C3—C4	0.3 (2)	C5—C4—C12—N2	179.96 (12)
C2—C3—C4—C12	−0.2 (2)	C3—C4—C12—C11	179.23 (12)
C2—C3—C4—C5	179.78 (15)	C5—C4—C12—C11	−0.71 (19)
C3—C4—C5—C6	−178.60 (15)	N1—C11—C12—N2	−0.78 (18)
C12—C4—C5—C6	1.3 (2)	C7—C11—C12—N2	178.68 (12)
C4—C5—C6—C7	−0.6 (3)	N1—C11—C12—C4	179.89 (12)
C5—C6—C7—C8	178.30 (15)	C7—C11—C12—C4	−0.65 (18)
C5—C6—C7—C11	−0.8 (2)	O1—C13—C14—O3	−2.66 (18)
C11—C7—C8—C9	−0.5 (2)	O2—C13—C14—O3	176.32 (9)
C6—C7—C8—C9	−179.65 (14)	O1—C13—C14—C15	118.25 (14)
C7—C8—C9—C10	−1.0 (2)	O2—C13—C14—C15	−62.78 (13)
C11—N1—C10—C9	−0.3 (2)	O3—C14—C15—O4	62.27 (11)
C8—C9—C10—N1	1.5 (2)	C13—C14—C15—O4	−59.41 (12)
C10—N1—C11—C7	−1.2 (2)	O3—C14—C15—C16	−57.81 (11)
C10—N1—C11—C12	178.18 (12)	C13—C14—C15—C16	−179.49 (9)
C8—C7—C11—N1	1.7 (2)	O4—C15—C16—O5	0.45 (14)
C6—C7—C11—N1	−179.15 (14)	C14—C15—C16—O5	122.63 (11)
C8—C7—C11—C12	−177.76 (12)	O4—C15—C16—O6	179.93 (9)
C6—C7—C11—C12	1.42 (19)	C14—C15—C16—O6	−57.89 (12)
C1—N2—C12—C4	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O6i	1.01 (4)	1.45 (4)	2.4554 (12)	174 (4)
O3—H3A···O8ii	0.86 (2)	1.86 (2)	2.6817 (13)	159 (2)
O4—H4A···O9i	0.81 (3)	1.90 (3)	2.7102 (13)	173 (3)
N2—H2B···O7	0.912 (19)	1.763 (19)	2.6426 (14)	161.3 (18)
O7—H7A···O6iii	0.91 (2)	1.87 (2)	2.7727 (13)	170 (2)
O7—H7B···O5	0.81 (3)	2.02 (3)	2.7141 (14)	144 (3)
O7—H7B···O4	0.81 (3)	2.36 (3)	3.0442 (14)	143 (3)
O8—H8A···O3i	0.85 (3)	1.90 (3)	2.7497 (13)	171 (2)
O8—H8B···O1	0.92 (3)	1.77 (3)	2.6730 (14)	165 (3)
O9—H9A···O2iii	0.87 (3)	2.15 (3)	2.9472 (14)	152 (3)
O9—H9B···O5	0.79 (3)	1.96 (3)	2.7452 (14)	179 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O6i	1.01 (4)	1.45 (4)	2.4554 (12)	174 (4)
O3—H3A⋯O8ii	0.86 (2)	1.86 (2)	2.6817 (13)	159 (2)
O4—H4A⋯O9i	0.81 (3)	1.90 (3)	2.7102 (13)	173 (3)
N2—H2B⋯O7	0.912 (19)	1.763 (19)	2.6426 (14)	161.3 (18)
O7—H7A⋯O6iii	0.91 (2)	1.87 (2)	2.7727 (13)	170 (2)
O7—H7B⋯O5	0.81 (3)	2.02 (3)	2.7141 (14)	144 (3)
O7—H7B⋯O4	0.81 (3)	2.36 (3)	3.0442 (14)	143 (3)
O8—H8A⋯O3i	0.85 (3)	1.90 (3)	2.7497 (13)	171 (2)
O8—H8B⋯O1	0.92 (3)	1.77 (3)	2.6730 (14)	165 (3)
O9—H9A⋯O2iii	0.87 (3)	2.15 (3)	2.9472 (14)	152 (3)
O9—H9B⋯O5	0.79 (3)	1.96 (3)	2.7452 (14)	179 (3)

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