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

Cheng, S.F.; Ng, S.W.

doi:10.1107/S1600536811015972

1,10-Phenanthrolin-1-ium hydrogen D,L-tartrate dihydrate

In the title hydrated molecular salt, C₁₂H₉N₂⁺·C₄H₅O₆⁻·2H₂O, 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 carboxylate end of another anion [O

O = 2.508 (2) Å] in a head-to-tail manner, forming a chain; the chains and water molecules interact, generating an O—H

O hydrogen-bonded layer. The cation binds to the layer by an N—H

O hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811015972/bt5536sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811015972/bt5536Isup2.hkl Contains datablock I

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.047
wR factor = 0.160
Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H    Uiso(max)/Uiso(min) ..       4.07 Ratio
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         44
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         25

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.10
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O
PLAT793_ALERT_4_G The Model has Chirality at C2      (Verify) ....          S
PLAT793_ALERT_4_G The Model has Chirality at C3      (Verify) ....          S

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

D-tartaric acid transfers one proton to 1,10-phenanthroline to yield 1,10-phenanthroline hydrogen D-tartrate, which separates from solution as a trihydrate. The hydrogen D-tartrate anions are connected in a head-to-tail fashion by an O–H_{carboxylic acid}···O_carboxyl hydrogen bond [O···O 2.455 (1) Å] (Derikvand & Olmstead, 2010). The identical feature should be presented in the L analog (Wang et al., 2006). The anion and water molecules are linked by extensive O–H···O hydrogen bonds into a three-dimensional network, with the cations occupying the cavities. Racemic tartaric furnishes the corresponding dihydrate. In C₁₂H₉N₂⁺ C₄H₅O₄^-.2H₂O (Scheme I, Fig. 1), the carboxylic acid –CO₂H end of one hydrogen (D,L)-tartrate anion forms a short hydrogen bond to the carboxylate –CO₂^- end of another anion [O···O 2.508 (2) Å] in a head-to-tail manner to form a chain; the chains and water molecules interact to generate an O–H···O hydrogen-bonded layer. The cation binds to the layer by an N–H···O hydrogen bond (Table 1).

Related literature top

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

Experimental top

D,L-Tartaric acid (2 mmol, 0.30 g) and 1,10-phenanthroline (0.33 mmol, 0.06 g) were dissolved in water (5 ml). The solution was heated briefly to dissolve the reactants. The solution was set aside for the growth of colorless crystals, which were isolated after 10 days. The bulk crystals were faintly tinted a shade of pink.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₂H₉N₂⁺ C₄H₅O₆^-.2H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded layer structure arising from tartrate–water interactions.

1,10-Phenanthrolin-1-ium hydrogen D,L-tartrate dihydrate top

Crystal data top

C₁₂H₉N₂⁺·C₄H₅O₆⁻·2H₂O	Z = 2
M_r = 366.32	F(000) = 384
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1012P)² + 0.1854P] where P = (F_o² + 2F_c²)/3
3635 reflections	(Δ/σ)_max = 0.001
267 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₂H₉N₂⁺·C₄H₅O₆⁻·2H₂O	γ = 103.903 (1)°
M_r = 366.32	V = 806.95 (14) Å³
Triclinic, P1	Z = 2
a = 7.0933 (7) Å	Mo Kα radiation
b = 10.5849 (11) Å	µ = 0.12 mm⁻¹
c = 11.4694 (11) Å	T = 100 K
α = 98.081 (1)°	0.40 × 0.10 × 0.10 mm
β = 100.350 (1)°

Data collection top

Bruker SMART APEX diffractometer	2880 reflections with I > 2σ(I)
7610 measured reflections	R_int = 0.028
3635 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.35 e Å⁻³
3635 reflections	Δρ_min = −0.31 e Å⁻³
267 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	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···O6^v	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) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z; (iii) x+1, y, z; (iv) −x, −y+2, −z+1; (v) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₂⁺·C₄H₅O₆⁻·2H₂O
M_r	366.32
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.0933 (7), 10.5849 (11), 11.4694 (11)
α, β, γ (°)	98.081 (1), 100.350 (1), 103.903 (1)
V (Å³)	806.95 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7610, 3635, 2880
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.160, 1.04
No. of reflections	3635
No. of parameters	267
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.31

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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···O1^iv	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···O6^v	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) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z; (iii) x+1, y, z; (iv) −x, −y+2, −z+1; (v) −x+1, −y+2, −z.

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Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

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