1,10-Phenanthrolinium–6-carboxy­pyridine-2-carboxyl­ate–1,10-phenanthroline–pyridine-2,6-dicarboxylic acid–ethanol–water (1/1/1/1/1/1)

Fu, A.-Y.; Wang, D.-Q.; Zhang, C.-L.

doi:10.1107/S1600536805027236

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1,10-Phenanthrolinium–6-carboxypyridine-2-carboxylate–1,10-phenanthroline–pyridine-2,6-dicarboxylic acid–ethanol–water (1/1/1/1/1/1)

A.-Y. Fu, D.-Q. Wang and C.-L. Zhang

In the title compound, C₁₂H₉N₂⁺·C₇H₅O₄N⁻·C₁₂H₈N₂·C₇H₄O₄N·C₂H₆O·H₂O, the cations are stacked along the b axis to form a column-like structure. The anions, ethanol molecules and water molecules are linked via O—H

O and O—H

N hydrogen bonds to form a zigzag sheet-like structure. The cationic columns and anionic sheets are alternately arranged along the c axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027236/ci6638sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027236/ci6638Isup2.hkl Contains datablock I

CCDC reference: 287509

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.060
wR factor = 0.141
Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         37 Perc.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.111
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.02
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   4 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
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The asymmetric unit of (I), contains a (C₁₂H₈N₂·C₁₂H₉N₂)⁺ cation, a (C₇H₅O₄N·C₇H₄O₄N)⁻ anion, a solvent ethanol molecule and a water molecule (Fig. 1). The N3—H3A···N5ⁱ hydrogen-bonded (see Table 2 for symmetry code) 1,10-phenanthrolinium and 1,10-phenanthroline molecules form a cation, and the O4—H4···O5ⁱⁱⁱ hydrogen-bonded pyridine-2,6-dicarboxylic acid and 6-carboxypyridine-2-carboxylate molecules form an anion. The C—O bond lengths of the carboxylate group [C14—O5 = 1.289 (4) Å and C14—O6 = 1.222 (5) Å] are not equal as the O4—H4···O5ⁱⁱⁱ [O···O = 2.440 (4) Å] hydrogen bond is stonger than the O9—H9···O6^v [O···O = 2.768 (5) Å] hydrogen bond. The other bond lengths and angles in the cation are comparable to corresponding values found in its complexes (Fu, Sun et al., 2004; Fu, Wang & Shen, 2004; Fu, Wang, Shen & Zhang, 2004; Fu, Fu & Yu, 2005), and those in the anion of (I) are consistent with the values found in its complexes (Fu, Wang & Liu, 2004; Fu, Wang & Sun, 2005).

In the crystal structure of (I), the cations are stacked along the b axis to form a column-like structure. The anions and ethanol and water molecules are linked via O—H···O and O—H···N hydrogen bonds (Table 2) to form a zigzag sheet-like structure. The cationic columns and anionic sheets are alternately arranged along the c axis (Fig. 2).

Experimental top

Phenanthroline (1 mmol) and dipicofinic acid (1 mmol) were dissolved in a 1:1 alcohol and distilled water solution (20 ml), and the resulting solution was allowed to stand in air. After 14 d, colourless prism-shaped crystals separated. These were collected, washed with water and dried in a vacuum over CaCl₂ (yield 41%). Elemental analysis found: C 63.17, H 4.44, N 10.98%; calculated for C₄₀H₃₄N₆O₁₀: C 63.32, H 4.51, N 11.08%.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of (I), showing the hydrogen-bonded interactions as dashed lines.

1,10-Phenanthrolinium–6-carboxypyridine-2-carboxylate–1,10- phenanthroline–pyridine-2,6-dicarboxylic acid–ethanol–water (1/1/1/1/1/1) top

Crystal data top

C₁₂H₉N₂⁺·C₇H₄NO₄⁻·C₁₂H₈N₂·C₇H₅NO₄·C₂H₆O·H₂O	F(000) = 1584
M_r = 758.73	D_x = 1.409 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1469 reflections
a = 20.802 (7) Å	θ = 2.6–20.2°
b = 7.861 (3) Å	µ = 0.10 mm⁻¹
c = 24.488 (6) Å	T = 293 K
β = 116.72 (2)°	Prism, colourless
V = 3577 (2) Å³	0.39 × 0.13 × 0.11 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	6314 independent reflections
Radiation source: fine-focus sealed tube	2335 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.111
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −24→20
T_min = 0.961, T_max = 0.989	k = −8→9
18072 measured reflections	l = −29→29

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0316P)²] where P = (F_o² + 2F_c²)/3
6314 reflections	(Δ/σ)_max = 0.001
512 parameters	Δρ_max = 0.32 e Å⁻³
3 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₂H₉N₂⁺·C₇H₄NO₄⁻·C₁₂H₈N₂·C₇H₅NO₄·C₂H₆O·H₂O	V = 3577 (2) Å³
M_r = 758.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.802 (7) Å	µ = 0.10 mm⁻¹
b = 7.861 (3) Å	T = 293 K
c = 24.488 (6) Å	0.39 × 0.13 × 0.11 mm
β = 116.72 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6314 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2335 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.989	R_int = 0.111
18072 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	3 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.32 e Å⁻³
6314 reflections	Δρ_min = −0.28 e Å⁻³
512 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
N1	0.31411 (17)	0.9708 (5)	0.43521 (14)	0.0332 (9)
N2	0.00145 (17)	0.6586 (4)	0.15388 (15)	0.0361 (10)
N3	0.44876 (18)	0.1812 (5)	0.26605 (15)	0.0400 (10)
H3A	0.4715	0.2073	0.2453	0.048*
N4	0.37995 (19)	0.3238 (5)	0.15210 (17)	0.0498 (11)
N5	0.44540 (19)	0.6706 (5)	0.27840 (16)	0.0438 (11)
N6	0.37732 (18)	0.8185 (5)	0.16442 (16)	0.0445 (11)
O1	0.42160 (16)	0.6114 (4)	0.50427 (14)	0.0562 (10)
O2	0.44797 (15)	0.8612 (4)	0.47770 (16)	0.0543 (9)
H2	0.4878	0.8180	0.4889	0.081*
O3	0.28155 (16)	1.3022 (4)	0.40165 (14)	0.0569 (10)
O4	0.16697 (15)	1.2283 (4)	0.34571 (13)	0.0543 (10)
H4	0.1626	1.3273	0.3341	0.081*
O5	0.13427 (14)	0.5049 (4)	0.29544 (12)	0.0470 (9)
O6	0.07446 (16)	0.3699 (4)	0.20677 (14)	0.0554 (10)
O7	−0.10034 (15)	0.6392 (5)	0.03873 (13)	0.0637 (11)
H7	−0.0709	0.5718	0.0624	0.096*
O8	−0.12805 (18)	0.9093 (5)	0.03834 (15)	0.0816 (13)
O9	0.02655 (19)	0.8510 (4)	0.41466 (15)	0.0834 (12)
H9	−0.0035	0.8705	0.3795	0.125*
O10	0.42593 (17)	0.2480 (4)	0.49538 (17)	0.0658 (11)
C1	0.4037 (2)	0.7489 (6)	0.4815 (2)	0.0369 (12)
C2	0.3273 (2)	0.8090 (6)	0.45379 (17)	0.0289 (11)
C3	0.2740 (2)	0.6941 (6)	0.44728 (18)	0.0421 (12)
H3	0.2854	0.5820	0.4600	0.051*
C4	0.2037 (2)	0.7489 (6)	0.42162 (19)	0.0450 (13)
H4A	0.1671	0.6755	0.4184	0.054*
C5	0.1885 (2)	0.9122 (6)	0.40099 (17)	0.0379 (12)
H5	0.1411	0.9506	0.3825	0.045*
C6	0.2446 (2)	1.0211 (6)	0.40797 (17)	0.0302 (11)
C7	0.2322 (2)	1.2013 (6)	0.38507 (19)	0.0382 (12)
C8	−0.0903 (3)	0.7904 (7)	0.0649 (2)	0.0516 (14)
C9	−0.0306 (2)	0.8025 (6)	0.12859 (19)	0.0341 (11)
C10	−0.0115 (2)	0.9592 (6)	0.1570 (2)	0.0475 (13)
H10	−0.0354	1.0575	0.1371	0.057*
C11	0.0437 (2)	0.9662 (6)	0.2154 (2)	0.0495 (14)
H11	0.0587	1.0696	0.2357	0.059*
C12	0.0761 (2)	0.8168 (6)	0.24278 (19)	0.0423 (13)
H12	0.1128	0.8176	0.2826	0.051*
C13	0.0544 (2)	0.6653 (6)	0.21143 (19)	0.0335 (11)
C14	0.0893 (2)	0.4982 (6)	0.2383 (2)	0.0383 (12)
C15	0.4845 (2)	0.1059 (6)	0.3195 (2)	0.0471 (13)
H15	0.5332	0.0821	0.3340	0.057*
C16	0.4493 (3)	0.0625 (6)	0.3539 (2)	0.0554 (15)
H16	0.4740	0.0077	0.3913	0.066*
C17	0.3789 (3)	0.1005 (6)	0.3327 (2)	0.0491 (14)
H17	0.3554	0.0738	0.3561	0.059*
C18	0.3407 (2)	0.1797 (6)	0.2759 (2)	0.0419 (12)
C19	0.3777 (2)	0.2191 (6)	0.2423 (2)	0.0356 (12)
C20	0.3419 (2)	0.2974 (6)	0.1833 (2)	0.0382 (12)
C21	0.2682 (3)	0.3347 (6)	0.1606 (2)	0.0475 (13)
C22	0.2347 (3)	0.4080 (7)	0.1022 (2)	0.0633 (16)
H22	0.1864	0.4387	0.0856	0.076*
C23	0.2719 (3)	0.4343 (7)	0.0699 (2)	0.0700 (17)
H23	0.2497	0.4806	0.0308	0.084*
C24	0.3439 (3)	0.3904 (7)	0.0965 (2)	0.0629 (16)
H24	0.3691	0.4089	0.0738	0.076*
C25	0.2663 (3)	0.2229 (7)	0.2514 (2)	0.0578 (15)
H25	0.2412	0.2000	0.2739	0.069*
C26	0.2325 (3)	0.2962 (7)	0.1964 (2)	0.0602 (16)
H26	0.1839	0.3227	0.1812	0.072*
C27	0.4753 (3)	0.5940 (7)	0.3322 (2)	0.0569 (15)
H27	0.5244	0.5714	0.3493	0.068*
C28	0.4385 (3)	0.5452 (6)	0.3648 (2)	0.0540 (14)
H28	0.4623	0.4899	0.4022	0.065*
C29	0.3671 (3)	0.5795 (6)	0.3412 (2)	0.0502 (14)
H29	0.3412	0.5466	0.3620	0.060*
C30	0.3329 (2)	0.6643 (6)	0.2854 (2)	0.0413 (12)
C31	0.3743 (2)	0.7054 (6)	0.25485 (19)	0.0374 (12)
C32	0.3391 (2)	0.7870 (6)	0.1956 (2)	0.0390 (12)
C33	0.2661 (2)	0.8329 (6)	0.1721 (2)	0.0446 (13)
C34	0.2338 (3)	0.9150 (6)	0.1161 (2)	0.0569 (15)
H34	0.1861	0.9498	0.1003	0.068*
C35	0.2717 (3)	0.9448 (6)	0.0841 (2)	0.0556 (15)
H35	0.2506	0.9979	0.0461	0.067*
C36	0.3428 (3)	0.8934 (6)	0.1100 (2)	0.0533 (14)
H36	0.3685	0.9124	0.0878	0.064*
C37	0.2586 (2)	0.7109 (7)	0.2593 (2)	0.0578 (15)
H37	0.2318	0.6842	0.2800	0.069*
C38	0.2272 (3)	0.7921 (7)	0.2058 (2)	0.0576 (15)
H38	0.1790	0.8227	0.1901	0.069*
C39	−0.0069 (3)	0.7685 (8)	0.4466 (2)	0.083 (2)
H39A	−0.0286	0.6625	0.4264	0.100*
H39B	−0.0442	0.8403	0.4476	0.100*
C40	0.0496 (3)	0.7347 (7)	0.5097 (3)	0.099 (2)
H40A	0.0284	0.6792	0.5326	0.149*
H40B	0.0708	0.8403	0.5291	0.149*
H40C	0.0860	0.6627	0.5081	0.149*
H1	0.419 (2)	0.357 (2)	0.492 (2)	0.080*
H6	0.3912 (18)	0.208 (5)	0.4647 (15)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.033 (2)	0.029 (3)	0.035 (2)	0.0005 (19)	0.0134 (18)	0.0010 (19)
N2	0.032 (2)	0.034 (3)	0.039 (2)	0.0043 (19)	0.0132 (19)	0.005 (2)
N3	0.040 (2)	0.048 (3)	0.037 (2)	−0.002 (2)	0.0207 (19)	0.003 (2)
N4	0.051 (3)	0.061 (3)	0.035 (2)	−0.005 (2)	0.017 (2)	0.003 (2)
N5	0.034 (2)	0.055 (3)	0.037 (2)	0.003 (2)	0.0109 (19)	−0.004 (2)
N6	0.041 (2)	0.054 (3)	0.037 (2)	−0.004 (2)	0.015 (2)	−0.004 (2)
O1	0.056 (2)	0.031 (2)	0.072 (2)	0.0115 (18)	0.0203 (18)	0.020 (2)
O2	0.033 (2)	0.041 (2)	0.083 (2)	0.0070 (17)	0.020 (2)	0.0167 (19)
O3	0.042 (2)	0.034 (2)	0.075 (2)	0.0018 (18)	0.0083 (18)	0.0144 (19)
O4	0.035 (2)	0.045 (2)	0.065 (2)	0.0104 (16)	0.0069 (17)	0.0259 (18)
O5	0.0407 (19)	0.045 (2)	0.0391 (19)	0.0039 (16)	0.0034 (16)	0.0079 (18)
O6	0.067 (2)	0.032 (2)	0.052 (2)	0.0131 (18)	0.0123 (18)	0.0030 (18)
O7	0.052 (2)	0.070 (3)	0.048 (2)	0.005 (2)	0.0032 (17)	0.008 (2)
O8	0.070 (3)	0.074 (3)	0.069 (3)	0.027 (2)	0.002 (2)	0.030 (2)
O9	0.097 (3)	0.066 (3)	0.060 (2)	−0.016 (2)	0.012 (2)	0.016 (2)
O10	0.040 (2)	0.052 (2)	0.086 (3)	−0.0015 (19)	0.0109 (19)	−0.011 (2)
C1	0.037 (3)	0.032 (3)	0.039 (3)	−0.001 (3)	0.015 (2)	−0.002 (3)
C2	0.031 (3)	0.022 (3)	0.028 (2)	−0.001 (2)	0.008 (2)	0.004 (2)
C3	0.051 (3)	0.028 (3)	0.042 (3)	0.000 (3)	0.015 (3)	0.004 (2)
C4	0.044 (3)	0.037 (3)	0.046 (3)	−0.008 (3)	0.014 (3)	0.005 (3)
C5	0.029 (3)	0.049 (4)	0.030 (3)	−0.001 (3)	0.009 (2)	−0.003 (3)
C6	0.029 (3)	0.031 (3)	0.026 (2)	0.001 (2)	0.008 (2)	−0.001 (2)
C7	0.031 (3)	0.043 (4)	0.038 (3)	0.004 (3)	0.014 (2)	0.004 (3)
C8	0.047 (3)	0.049 (4)	0.051 (4)	0.004 (3)	0.016 (3)	0.011 (3)
C9	0.028 (3)	0.034 (3)	0.037 (3)	0.006 (2)	0.012 (2)	0.010 (3)
C10	0.039 (3)	0.038 (4)	0.063 (3)	0.013 (3)	0.020 (3)	0.013 (3)
C11	0.045 (3)	0.029 (3)	0.066 (4)	0.007 (3)	0.018 (3)	−0.004 (3)
C12	0.038 (3)	0.040 (3)	0.038 (3)	0.006 (3)	0.007 (2)	−0.002 (3)
C13	0.031 (3)	0.033 (3)	0.035 (3)	−0.001 (2)	0.014 (2)	−0.002 (3)
C14	0.033 (3)	0.030 (3)	0.047 (3)	0.007 (3)	0.014 (3)	0.010 (3)
C15	0.041 (3)	0.050 (4)	0.043 (3)	0.006 (3)	0.012 (3)	0.006 (3)
C16	0.074 (4)	0.048 (4)	0.051 (3)	−0.003 (3)	0.034 (3)	0.008 (3)
C17	0.052 (3)	0.049 (4)	0.058 (4)	−0.011 (3)	0.036 (3)	−0.009 (3)
C18	0.051 (3)	0.043 (3)	0.039 (3)	−0.003 (3)	0.026 (3)	−0.009 (3)
C19	0.031 (3)	0.039 (3)	0.036 (3)	−0.006 (2)	0.015 (2)	−0.007 (2)
C20	0.035 (3)	0.041 (3)	0.036 (3)	−0.007 (2)	0.014 (3)	−0.011 (2)
C21	0.043 (3)	0.049 (4)	0.044 (3)	0.000 (3)	0.014 (3)	−0.011 (3)
C22	0.050 (4)	0.071 (5)	0.048 (4)	0.001 (3)	0.004 (3)	−0.003 (3)
C23	0.073 (4)	0.076 (5)	0.044 (4)	0.003 (4)	0.012 (3)	0.009 (3)
C24	0.060 (4)	0.074 (5)	0.044 (3)	−0.012 (3)	0.015 (3)	0.005 (3)
C25	0.044 (3)	0.075 (5)	0.066 (4)	−0.010 (3)	0.034 (3)	−0.018 (3)
C26	0.034 (3)	0.082 (5)	0.059 (4)	0.007 (3)	0.015 (3)	−0.016 (3)
C27	0.042 (3)	0.075 (4)	0.052 (3)	0.001 (3)	0.018 (3)	0.000 (3)
C28	0.065 (4)	0.054 (4)	0.042 (3)	0.000 (3)	0.024 (3)	−0.004 (3)
C29	0.061 (4)	0.043 (4)	0.057 (3)	−0.010 (3)	0.036 (3)	−0.008 (3)
C30	0.044 (3)	0.034 (3)	0.048 (3)	−0.005 (3)	0.023 (3)	−0.006 (3)
C31	0.038 (3)	0.034 (3)	0.037 (3)	−0.004 (2)	0.015 (3)	−0.008 (2)
C32	0.034 (3)	0.032 (3)	0.048 (3)	−0.004 (2)	0.015 (3)	−0.009 (3)
C33	0.039 (3)	0.040 (3)	0.050 (3)	−0.001 (3)	0.016 (3)	−0.009 (3)
C34	0.043 (3)	0.054 (4)	0.059 (4)	0.006 (3)	0.010 (3)	−0.003 (3)
C35	0.063 (4)	0.048 (4)	0.039 (3)	0.006 (3)	0.008 (3)	−0.002 (3)
C36	0.060 (4)	0.052 (4)	0.044 (3)	−0.004 (3)	0.020 (3)	−0.004 (3)
C37	0.042 (3)	0.071 (4)	0.069 (4)	−0.007 (3)	0.033 (3)	−0.004 (3)
C38	0.037 (3)	0.069 (4)	0.070 (4)	0.002 (3)	0.027 (3)	0.001 (3)
C39	0.088 (5)	0.102 (6)	0.065 (4)	0.002 (4)	0.039 (4)	−0.003 (4)
C40	0.098 (5)	0.105 (6)	0.093 (5)	0.023 (4)	0.041 (4)	0.029 (4)

Geometric parameters (Å, º) top

N1—C2	1.337 (5)	C15—C16	1.385 (6)
N1—C6	1.351 (4)	C15—H15	0.93
N2—C9	1.317 (5)	C16—C17	1.349 (6)
N2—C13	1.344 (4)	C16—H16	0.9300
N3—C15	1.319 (5)	C17—C18	1.400 (6)
N3—C19	1.355 (5)	C17—H17	0.93
N3—H3A	0.86	C18—C19	1.391 (5)
N4—C24	1.332 (5)	C18—C25	1.426 (6)
N4—C20	1.340 (5)	C19—C20	1.434 (5)
N5—C27	1.322 (5)	C20—C21	1.407 (5)
N5—C31	1.352 (5)	C21—C22	1.403 (6)
N6—C36	1.333 (5)	C21—C26	1.412 (6)
N6—C32	1.350 (5)	C22—C23	1.348 (6)
O1—C1	1.196 (5)	C22—H22	0.93
O2—C1	1.309 (5)	C23—C24	1.382 (6)
O2—H2	0.82	C23—H23	0.93
O3—C7	1.213 (5)	C24—H24	0.93
O4—C7	1.281 (4)	C25—C26	1.339 (6)
O4—H4	0.82	C25—H25	0.93
O5—C14	1.289 (4)	C26—H26	0.93
O6—C14	1.222 (5)	C27—C28	1.385 (6)
O7—C8	1.321 (5)	C27—H27	0.93
O7—H7	0.82	C28—C29	1.357 (6)
O8—C8	1.206 (5)	C28—H28	0.93
O9—C39	1.415 (6)	C29—C30	1.393 (6)
O9—H9	0.82	C29—H29	0.93
O10—H1	0.868 (18)	C30—C31	1.409 (6)
O10—H6	0.836 (18)	C30—C37	1.429 (6)
C1—C2	1.496 (5)	C31—C32	1.449 (5)
C2—C3	1.383 (5)	C32—C33	1.408 (5)
C3—C4	1.374 (5)	C33—C34	1.386 (6)
C3—H3	0.93	C33—C38	1.427 (6)
C4—C5	1.364 (6)	C34—C35	1.358 (6)
C4—H4A	0.93	C34—H34	0.93
C5—C6	1.395 (5)	C35—C36	1.382 (6)
C5—H5	0.93	C35—H35	0.93
C6—C7	1.503 (6)	C36—H36	0.93
C8—C9	1.498 (6)	C37—C38	1.336 (6)
C9—C10	1.382 (6)	C37—H37	0.93
C10—C11	1.375 (5)	C38—H38	0.93
C10—H10	0.93	C39—C40	1.485 (6)
C11—C12	1.370 (5)	C39—H39A	0.97
C11—H11	0.93	C39—H39B	0.97
C12—C13	1.378 (5)	C40—H40A	0.96
C12—H12	0.93	C40—H40B	0.96
C13—C14	1.502 (6)	C40—H40C	0.96

C2—N1—C6	117.2 (4)	N4—C20—C21	124.1 (4)
C9—N2—C13	117.5 (4)	N4—C20—C19	118.0 (4)
C15—N3—C19	122.9 (4)	C21—C20—C19	117.8 (5)
C15—N3—H3A	118.5	C22—C21—C20	116.2 (5)
C19—N3—H3A	118.5	C22—C21—C26	124.2 (5)
C24—N4—C20	116.0 (4)	C20—C21—C26	119.7 (5)
C27—N5—C31	116.9 (4)	C23—C22—C21	120.6 (5)
C36—N6—C32	117.2 (4)	C23—C22—H22	119.7
C1—O2—H2	109.5	C21—C22—H22	119.7
C7—O4—H4	109.5	C22—C23—C24	118.2 (5)
C8—O7—H7	109.5	C22—C23—H23	120.9
C39—O9—H9	109.5	C24—C23—H23	120.9
H1—O10—H6	105 (3)	N4—C24—C23	124.9 (5)
O1—C1—O2	124.2 (4)	N4—C24—H24	117.5
O1—C1—C2	122.7 (4)	C23—C24—H24	117.5
O2—C1—C2	113.1 (4)	C26—C25—C18	120.3 (5)
N1—C2—C3	123.4 (4)	C26—C25—H25	119.8
N1—C2—C1	117.9 (4)	C18—C25—H25	119.8
C3—C2—C1	118.7 (4)	C25—C26—C21	122.1 (5)
C4—C3—C2	118.8 (4)	C25—C26—H26	118.9
C4—C3—H3	120.6	C21—C26—H26	118.9
C2—C3—H3	120.6	N5—C27—C28	124.5 (5)
C5—C4—C3	119.1 (4)	N5—C27—H27	117.8
C5—C4—H4A	120.4	C28—C27—H27	117.8
C3—C4—H4A	120.4	C29—C28—C27	118.8 (5)
C4—C5—C6	119.3 (4)	C29—C28—H28	120.6
C4—C5—H5	120.3	C27—C28—H28	120.6
C6—C5—H5	120.3	C28—C29—C30	119.5 (5)
N1—C6—C5	122.1 (4)	C28—C29—H29	120.3
N1—C6—C7	115.2 (4)	C30—C29—H29	120.3
C5—C6—C7	122.6 (4)	C29—C30—C31	117.7 (4)
O3—C7—O4	126.5 (5)	C29—C30—C37	122.2 (5)
O3—C7—C6	121.0 (4)	C31—C30—C37	120.0 (5)
O4—C7—C6	112.5 (4)	N5—C31—C30	122.7 (4)
O8—C8—O7	120.9 (5)	N5—C31—C32	118.7 (4)
O8—C8—C9	123.1 (5)	C30—C31—C32	118.6 (4)
O7—C8—C9	116.0 (5)	N6—C32—C33	121.6 (4)
N2—C9—C10	124.0 (4)	N6—C32—C31	119.1 (4)
N2—C9—C8	116.2 (4)	C33—C32—C31	119.3 (5)
C10—C9—C8	119.8 (4)	C34—C33—C32	118.4 (5)
C11—C10—C9	118.4 (4)	C34—C33—C38	121.9 (5)
C11—C10—H10	120.8	C32—C33—C38	119.7 (5)
C9—C10—H10	120.8	C35—C34—C33	120.2 (5)
C12—C11—C10	118.1 (4)	C35—C34—H34	119.9
C12—C11—H11	120.9	C33—C34—H34	119.9
C10—C11—H11	120.9	C34—C35—C36	117.7 (5)
C11—C12—C13	120.1 (4)	C34—C35—H35	121.2
C11—C12—H12	119.9	C36—C35—H35	121.2
C13—C12—H12	119.9	N6—C36—C35	124.8 (5)
N2—C13—C12	121.8 (4)	N6—C36—H36	117.6
N2—C13—C14	115.6 (4)	C35—C36—H36	117.6
C12—C13—C14	122.6 (4)	C38—C37—C30	121.0 (5)
O6—C14—O5	125.0 (4)	C38—C37—H37	119.5
O6—C14—C13	120.7 (4)	C30—C37—H37	119.5
O5—C14—C13	114.3 (4)	C37—C38—C33	121.3 (5)
N3—C15—C16	119.9 (4)	C37—C38—H38	119.3
N3—C15—H15	120.0	C33—C38—H38	119.3
C16—C15—H15	120.0	O9—C39—C40	107.6 (5)
C17—C16—C15	119.3 (5)	O9—C39—H39A	110.2
C17—C16—H16	120.3	C40—C39—H39A	110.2
C15—C16—H16	120.3	O9—C39—H39B	110.2
C16—C17—C18	121.0 (5)	C40—C39—H39B	110.2
C16—C17—H17	119.5	H39A—C39—H39B	108.5
C18—C17—H17	119.5	C39—C40—H40A	109.5
C19—C18—C17	117.9 (4)	C39—C40—H40B	109.5
C19—C18—C25	118.9 (5)	H40A—C40—H40B	109.5
C17—C18—C25	123.1 (5)	C39—C40—H40C	109.5
N3—C19—C18	119.0 (4)	H40A—C40—H40C	109.5
N3—C19—C20	119.9 (4)	H40B—C40—H40C	109.5
C18—C19—C20	121.1 (4)

C6—N1—C2—C3	−1.0 (6)	N3—C19—C20—N4	2.8 (6)
C6—N1—C2—C1	177.3 (3)	C18—C19—C20—N4	−176.6 (4)
O1—C1—C2—N1	173.2 (4)	N3—C19—C20—C21	−179.8 (4)
O2—C1—C2—N1	−7.2 (6)	C18—C19—C20—C21	0.7 (6)
O1—C1—C2—C3	−8.4 (7)	N4—C20—C21—C22	−1.6 (7)
O2—C1—C2—C3	171.2 (4)	C19—C20—C21—C22	−178.7 (4)
N1—C2—C3—C4	−1.4 (6)	N4—C20—C21—C26	177.7 (5)
C1—C2—C3—C4	−179.7 (4)	C19—C20—C21—C26	0.6 (7)
C2—C3—C4—C5	2.8 (6)	C20—C21—C22—C23	2.1 (7)
C3—C4—C5—C6	−1.8 (6)	C26—C21—C22—C23	−177.2 (5)
C2—N1—C6—C5	2.1 (6)	C21—C22—C23—C24	−1.3 (8)
C2—N1—C6—C7	−177.0 (4)	C20—N4—C24—C23	0.6 (7)
C4—C5—C6—N1	−0.7 (6)	C22—C23—C24—N4	−0.1 (8)
C4—C5—C6—C7	178.4 (4)	C19—C18—C25—C26	1.7 (7)
N1—C6—C7—O3	−15.1 (6)	C17—C18—C25—C26	−179.0 (5)
C5—C6—C7—O3	165.8 (4)	C18—C25—C26—C21	−0.4 (8)
N1—C6—C7—O4	161.8 (3)	C22—C21—C26—C25	178.5 (5)
C5—C6—C7—O4	−17.3 (6)	C20—C21—C26—C25	−0.8 (8)
C13—N2—C9—C10	2.0 (6)	C31—N5—C27—C28	1.3 (7)
C13—N2—C9—C8	−178.8 (4)	N5—C27—C28—C29	−1.1 (8)
O8—C8—C9—N2	173.6 (5)	C27—C28—C29—C30	−0.8 (7)
O7—C8—C9—N2	−5.9 (6)	C28—C29—C30—C31	2.3 (7)
O8—C8—C9—C10	−7.3 (7)	C28—C29—C30—C37	−177.2 (4)
O7—C8—C9—C10	173.3 (4)	C27—N5—C31—C30	0.4 (6)
N2—C9—C10—C11	−0.6 (7)	C27—N5—C31—C32	−179.1 (4)
C8—C9—C10—C11	−179.8 (4)	C29—C30—C31—N5	−2.2 (7)
C9—C10—C11—C12	−1.2 (7)	C37—C30—C31—N5	177.3 (4)
C10—C11—C12—C13	1.6 (7)	C29—C30—C31—C32	177.4 (4)
C9—N2—C13—C12	−1.6 (6)	C37—C30—C31—C32	−3.1 (6)
C9—N2—C13—C14	−180.0 (4)	C36—N6—C32—C33	−0.8 (6)
C11—C12—C13—N2	−0.2 (7)	C36—N6—C32—C31	179.8 (4)
C11—C12—C13—C14	178.0 (4)	N5—C31—C32—N6	3.1 (6)
N2—C13—C14—O6	7.1 (6)	C30—C31—C32—N6	−176.4 (4)
C12—C13—C14—O6	−171.3 (4)	N5—C31—C32—C33	−176.3 (4)
N2—C13—C14—O5	−172.9 (4)	C30—C31—C32—C33	4.1 (6)
C12—C13—C14—O5	8.8 (6)	N6—C32—C33—C34	−1.1 (7)
C19—N3—C15—C16	−0.1 (7)	C31—C32—C33—C34	178.3 (4)
N3—C15—C16—C17	−1.1 (7)	N6—C32—C33—C38	178.0 (4)
C15—C16—C17—C18	1.4 (7)	C31—C32—C33—C38	−2.6 (6)
C16—C17—C18—C19	−0.5 (7)	C32—C33—C34—C35	2.1 (7)
C16—C17—C18—C25	−179.8 (5)	C38—C33—C34—C35	−177.0 (5)
C15—N3—C19—C18	1.0 (6)	C33—C34—C35—C36	−1.2 (7)
C15—N3—C19—C20	−178.5 (4)	C32—N6—C36—C35	1.8 (7)
C17—C18—C19—N3	−0.6 (6)	C34—C35—C36—N6	−0.9 (7)
C25—C18—C19—N3	178.7 (4)	C29—C30—C37—C38	−180.0 (5)
C17—C18—C19—C20	178.8 (4)	C31—C30—C37—C38	0.6 (7)
C25—C18—C19—C20	−1.8 (7)	C30—C37—C38—C33	1.1 (8)
C24—N4—C20—C21	0.3 (7)	C34—C33—C38—C37	179.0 (5)
C24—N4—C20—C19	177.4 (4)	C32—C33—C38—C37	0.0 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N5ⁱ	0.86	2.08	2.863 (5)	152
O2—H2···O10ⁱⁱ	0.82	1.74	2.549 (4)	170
O4—H4···O5ⁱⁱⁱ	0.82	1.64	2.440 (4)	164
O7—H7···O9^iv	0.82	1.93	2.686 (5)	154
O7—H7···N2	0.82	2.17	2.662 (4)	118
O9—H9···O6^v	0.82	1.96	2.768 (5)	169
O9—H9···N2^v	0.82	2.41	2.850 (5)	114
O10—H1···O1	0.87 (2)	2.02 (2)	2.869 (5)	167 (4)
O10—H6···O3^vi	0.84 (2)	2.23 (4)	2.876 (4)	134 (4)
O10—H6···N1^vi	0.84 (2)	2.35 (3)	3.041 (5)	140 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₂⁺·C₇H₄NO₄⁻·C₁₂H₈N₂·C₇H₅NO₄·C₂H₆O·H₂O
M_r	758.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	20.802 (7), 7.861 (3), 24.488 (6)
β (°)	116.72 (2)
V (Å³)	3577 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.39 × 0.13 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.961, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	18072, 6314, 2335
R_int	0.111
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.141, 1.00
No. of reflections	6314
No. of parameters	512
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003), SHELXL97.

Selected geometric parameters (Å, º) top

O1—C1	1.196 (5)	O4—C7	1.281 (4)
O2—C1	1.309 (5)	O7—C8	1.321 (5)
O3—C7	1.213 (5)	O8—C8	1.206 (5)

O1—C1—O2	124.2 (4)	O8—C8—O7	120.9 (5)
O1—C1—C2	122.7 (4)	O8—C8—C9	123.1 (5)
O2—C1—C2	113.1 (4)	O7—C8—C9	116.0 (5)
O3—C7—O4	126.5 (5)	O6—C14—O5	125.0 (4)
O3—C7—C6	121.0 (4)	O6—C14—C13	120.7 (4)
O4—C7—C6	112.5 (4)	O5—C14—C13	114.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N5ⁱ	0.86	2.08	2.863 (5)	152
O2—H2···O10ⁱⁱ	0.82	1.74	2.549 (4)	170
O4—H4···O5ⁱⁱⁱ	0.82	1.64	2.440 (4)	164
O7—H7···O9^iv	0.82	1.93	2.686 (5)	154
O7—H7···N2	0.82	2.17	2.662 (4)	118
O9—H9···O6^v	0.82	1.96	2.768 (5)	169
O9—H9···N2^v	0.82	2.41	2.850 (5)	114
O10—H1···O1	0.868 (18)	2.02 (2)	2.869 (5)	167 (4)
O10—H6···O3^vi	0.836 (18)	2.23 (4)	2.876 (4)	134 (4)
O10—H6···N1^vi	0.836 (18)	2.35 (3)	3.041 (5)	140 (4)

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

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