Diphenic acid–acridine (1/1)

Shaameri, Z.; Shan, N.; Jones, W.

doi:10.1107/S160053680101618X

Diphenic acid–acridine (1/1)

The structure of the title complex, C₁₄H₁₀O₄.C₁₃H₉N, which was cocrystallized from an ethanol solution containing a 1:1 mixture of diphenic acid and acridine, has been determined. Hydrogen bonding exists between acid–acid and acid–base as well as acridine π–π interactions. Proton transfer occurs in one of the two carboxylic acid–aromatic nitrogen interactions.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680101618X/tk6040sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680101618X/tk6040Isup2.hkl Contains datablock I

CCDC reference: 176023

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.008 Å
Disorder in main residue
R factor = 0.064
wR factor = 0.211
Data-to-parameter ratio = 12.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_301  Alert C Main Residue Disorder ........................       2.00 Perc.

PLAT_745  Alert C D-H     Calc     0.83(5), Rep     0.84000 ....    Missing s.u.
                     O1   -H01     1.555   1.555

PLAT_745  Alert C D-H     Calc     0.86(5), Rep     0.85000 ....    Missing s.u.
                     O7   -H03     1.555   1.555

PLAT_745  Alert C D-H     Calc     0.84(5), Rep     0.84000 ....    Missing s.u.
                     O5   -H02     1.555   1.555

PLAT_746  Alert C H...A   Calc     1.75(5), Rep     1.74000 ....    Missing s.u.
                     H01  -O4      1.555   1.555

PLAT_746  Alert C H...A   Calc     1.74(5), Rep     1.75000 ....    Missing s.u.
                     H03  -O3      1.555   1.555

PLAT_746  Alert C H...A   Calc     1.86(4), Rep     1.86000 ....    Missing s.u.
                     H02  -N1      1.555   2.755

PLAT_748  Alert C D-H..A  Calc      177(8), Rep      178.00 ....    Missing s.u.
                     O1   -H01  -O4      1.555   1.555   1.555

PLAT_748  Alert C D-H..A  Calc      173(5), Rep      173.00 ....    Missing s.u.
                     O7   -H03  -O3      1.555   1.555   1.555


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 9 Alert Level C = Please check

Comment top

Diphenic acid (biphenyl-2,2'-dicarboxylic acid), (I), forms infinite zigzag acid chains via R₂²(8) carboxylic acid pairs (Fronczek et al., 1987). It is of interest since it is potentially a good building block in crystal engineering with organic bases. To date, no organic co-crystal structure involving diphenic acid exists in the Cambridge Structural Database (CONQUEST 1.2, 2001). We report here the first diphenic acid co-crystal structure with acridine as the base.

The asymmetric unit of complex (I) comprises of two acid and two base molecules (Fig. 1). The torsion angles of the two phenyl rings are approximately 72° and 89°, respectively. A two-acid–two-base unit exists (Fig. 2), involving an O1—H01···O4 intramolecular hydrogen bond, an O7—H03···O3 acid–acid interaction and several acid–base intermolecular interactions (Table 2). In one of the two pairs of acid–base contacts, proton transfer occurs from the carboxylic acid group O3—C14—O4 to aromatic N2, evidenced by the O3—C14 and O4—C14 bond distances (Table 1). H02, the proton involved in the other acid–base contact (located from the difference map) remains within the carboxylic group attached to O5. The O6 site was refined with disorder over two distinct positions (O6A & O6B) with equal occupancy, and possible weak hydrogen bonds C40—H40—O6A and C40—H40—O6B are noted. An infinite supramolecular unit is formed along the a axis by packing the two-acid–two-base units via π-π interactions between acridine molecules. Acridine molecular planes are approximately perpendicular to the a axis, with a distance of approximately 3.5 Å between adjacent planes (Fig. 2). The infinite supramolecular units pack assemble via close packing (Fig. 3).

Experimental top

Diphenic acid and acridine were obtained from Aldrich. 28 mg of the acid and 18 mg of the base were dissolved in 15 ml of ethanol. Crystals were obtained by slow evaporation of the ethanol solution at the room temperature.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1988); cell refinement: CAD-4 Software (SETANG); data reduction: TEXSAN(Molecular Structure Corporation, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1993); software used to prepare material for publication: SHELXL97).

Figures top

	Fig. 1. The asymmetric unit of (I) showing displacement ellipsoids at the 30% probability level. H atoms bonded to carbon have been omitted for clarity (Sheldrick, 1993).
	Fig. 2. Projection of the molecular packing of (I) onto the (010) plane showing the acridine molecules stacked along the a axis. (Watkin et al., 1996).
	Fig. 3. Projection onto (100) showing the packing of the infinite supramolecular unit. (Watkin et al., 1996).

Diphenic acid–acridine (1/1) top

Crystal data top

C₁₄H₁₀O₄·C₁₄H₉O₄⁻·C₁₃H₉N·C₁₃H₁₀N⁺	D_x = 1.347 Mg m⁻³
M_r = 842.86	Melting point: not measured K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.461 (3) Å	Cell parameters from 25 reflections
b = 15.863 (3) Å	θ = 8.0–15.0°
c = 19.166 (3) Å	µ = 0.09 mm⁻¹
β = 108.98 (2)°	T = 295 K
V = 4157.5 (13) Å³	Block, yellow
Z = 4	0.30 × 0.30 × 0.20 mm
F(000) = 1760

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.045
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 3.6°
Graphite monochromator	h = −17→16
ω/2θ scans	k = 0→18
7509 measured reflections	l = 0→22
7275 independent reflections	3 standard reflections every 200 reflections
3160 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.211	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0914P)²] where P = (F_o² + 2F_c²)/3
7275 reflections	(Δ/σ)_max = 0.002
598 parameters	Δρ_max = 0.23 e Å⁻³
3 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₄H₁₀O₄·C₁₄H₉O₄⁻·C₁₃H₉N·C₁₃H₁₀N⁺	V = 4157.5 (13) Å³
M_r = 842.86	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.461 (3) Å	µ = 0.09 mm⁻¹
b = 15.863 (3) Å	T = 295 K
c = 19.166 (3) Å	0.30 × 0.30 × 0.20 mm
β = 108.98 (2)°

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.045
7509 measured reflections	3 standard reflections every 200 reflections
7275 independent reflections	intensity decay: none
3160 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.064	3 restraints
wR(F²) = 0.211	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.23 e Å⁻³
7275 reflections	Δρ_min = −0.25 e Å⁻³
598 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	Occ. (<1)
H01	0.498 (3)	0.470 (5)	0.208 (3)	0.15 (4)*
O1	0.4420 (3)	0.4601 (2)	0.1793 (2)	0.0636 (10)
O2	0.3023 (3)	0.5244 (2)	0.1240 (2)	0.0708 (11)
O3	0.7697 (2)	0.5046 (2)	0.27410 (16)	0.0540 (9)
O4	0.6161 (3)	0.4858 (2)	0.26916 (18)	0.0632 (10)
C8	0.6443 (3)	0.5338 (3)	0.1611 (2)	0.0427 (11)
C14	0.6786 (4)	0.5062 (3)	0.2403 (2)	0.0465 (12)
C2	0.4360 (3)	0.6095 (3)	0.1934 (2)	0.0444 (11)
C7	0.5678 (3)	0.5905 (3)	0.1335 (2)	0.0366 (10)
C1	0.5214 (3)	0.6365 (3)	0.1817 (2)	0.0406 (11)
C11	0.5836 (4)	0.5761 (3)	0.0127 (3)	0.0524 (13)
H11	0.5621	0.5897	−0.0372	0.063*
C9	0.6905 (4)	0.5006 (3)	0.1131 (3)	0.0521 (12)
H9	0.7435	0.4643	0.1312	0.063*
C12	0.5395 (3)	0.6116 (3)	0.0589 (2)	0.0475 (12)
H12	0.4895	0.6506	0.0401	0.057*
C6	0.5609 (4)	0.7140 (3)	0.2107 (3)	0.0551 (13)
H6	0.6170	0.7340	0.2027	0.066*
C10	0.6582 (4)	0.5213 (3)	0.0397 (3)	0.0542 (13)
H10	0.6879	0.4973	0.0081	0.065*
C13	0.3868 (4)	0.5286 (3)	0.1622 (3)	0.0512 (12)
C3	0.3930 (4)	0.6585 (3)	0.2339 (3)	0.0603 (14)
H3	0.3358	0.6402	0.2414	0.072*
C5	0.5163 (5)	0.7615 (3)	0.2515 (3)	0.0713 (17)
H5	0.5432	0.8130	0.2712	0.086*
C4	0.4339 (5)	0.7334 (4)	0.2630 (3)	0.0742 (17)
H4	0.4051	0.7655	0.2910	0.089*
H03	0.861 (3)	0.544 (3)	0.242 (3)	0.08 (2)*
O7	0.9094 (3)	0.5653 (2)	0.2317 (2)	0.0607 (9)
O5	1.1873 (3)	0.5394 (2)	0.2677 (2)	0.0655 (10)
H02	1.228 (5)	0.531 (5)	0.310 (2)	0.16 (4)*
O6A	1.2233 (10)	0.4118 (8)	0.2447 (7)	0.104 (4)	0.50
O6B	1.1697 (9)	0.4049 (7)	0.2685 (7)	0.101 (5)	0.50
C15	1.0219 (3)	0.5484 (3)	0.1355 (2)	0.0458 (12)
C21	1.0477 (3)	0.6347 (3)	0.1661 (2)	0.0439 (11)
C16	1.0725 (3)	0.4755 (3)	0.1634 (2)	0.0441 (11)
C22	0.9903 (4)	0.6801 (3)	0.1990 (2)	0.0516 (13)
C26	1.1275 (4)	0.6757 (3)	0.1567 (3)	0.0573 (13)
H26	1.1657	0.6473	0.1336	0.069*
C17	1.0415 (4)	0.3984 (3)	0.1276 (3)	0.0598 (14)
H17	1.0752	0.3493	0.1469	0.072*
C28	0.9010 (4)	0.6449 (4)	0.2125 (3)	0.0604 (14)
C19	0.9100 (4)	0.4657 (4)	0.0357 (3)	0.0704 (16)
H19	0.8558	0.4630	−0.0068	0.084*
C18	0.9620 (4)	0.3943 (4)	0.0644 (3)	0.0711 (16)
H18	0.9433	0.3428	0.0409	0.085*
O8	0.8293 (3)	0.6857 (3)	0.2072 (3)	0.1088 (17)
C20	0.9394 (4)	0.5413 (4)	0.0711 (3)	0.0634 (15)
H20	0.9038	0.5896	0.0519	0.076*
C27	1.1572 (4)	0.4702 (3)	0.2327 (3)	0.0613 (14)
C23	1.0136 (4)	0.7632 (3)	0.2208 (3)	0.0640 (15)
H23	0.9739	0.7933	0.2415	0.077*
C24	1.0940 (5)	0.8015 (4)	0.2123 (3)	0.0741 (17)
H24	1.1096	0.8568	0.2277	0.089*
C25	1.1517 (4)	0.7566 (4)	0.1804 (3)	0.0732 (17)
H25	1.2073	0.7815	0.1750	0.088*
N1	0.6889 (3)	0.0480 (2)	0.0941 (2)	0.0447 (10)
C41	0.6445 (3)	−0.0175 (3)	0.0507 (2)	0.0432 (11)
C36	0.6100 (3)	−0.0109 (3)	−0.0277 (3)	0.0463 (12)
C29	0.6962 (3)	0.1226 (3)	0.0616 (3)	0.0447 (11)
C35	0.6196 (3)	0.0646 (3)	−0.0587 (3)	0.0537 (13)
H35	0.5974	0.0698	−0.1098	0.064*
C34	0.6616 (3)	0.1340 (3)	−0.0159 (3)	0.0475 (12)
C40	0.6353 (3)	−0.0946 (3)	0.0839 (3)	0.0540 (13)
H40	0.6583	−0.0998	0.1350	0.065*
C30	0.7421 (4)	0.1908 (3)	0.1083 (3)	0.0579 (14)
H30	0.7648	0.1844	0.1593	0.069*
C37	0.5678 (4)	−0.0835 (4)	−0.0693 (3)	0.0618 (14)
H37	0.5457	−0.0810	−0.1205	0.074*
C38	0.5596 (4)	−0.1562 (4)	−0.0352 (3)	0.0669 (15)
H38	0.5314	−0.2032	−0.0630	0.080*
C33	0.6719 (4)	0.2141 (4)	−0.0451 (3)	0.0612 (14)
H33	0.6485	0.2227	−0.0959	0.073*
C39	0.5931 (4)	−0.1610 (3)	0.0414 (3)	0.0671 (15)
H39	0.5862	−0.2114	0.0640	0.081*
C32	0.7150 (4)	0.2776 (3)	−0.0002 (4)	0.0700 (16)
H32	0.7205	0.3301	−0.0201	0.084*
C31	0.7521 (4)	0.2659 (3)	0.0766 (4)	0.0705 (16)
H31	0.7840	0.3102	0.1065	0.085*
N2	0.1773 (3)	0.0562 (2)	0.0821 (2)	0.0458 (10)
H2	0.1920	0.0395	0.1271	0.055*
C54	0.1363 (3)	−0.0001 (3)	0.0277 (2)	0.0421 (11)
C53	0.1143 (3)	−0.0815 (3)	0.0456 (3)	0.0523 (12)
H53	0.1286	−0.0978	0.0945	0.063*
C42	0.1963 (3)	0.1374 (3)	0.0695 (3)	0.0489 (12)
C49	0.1158 (3)	0.0250 (3)	−0.0458 (3)	0.0488 (12)
C48	0.1413 (3)	0.1067 (4)	−0.0602 (3)	0.0606 (15)
H48	0.1324	0.1229	−0.1086	0.073*
C47	0.1795 (3)	0.1635 (3)	−0.0038 (3)	0.0555 (13)
C52	0.0718 (4)	−0.1360 (3)	−0.0098 (4)	0.0656 (15)
H52	0.0574	−0.1905	0.0014	0.079*
C50	0.0706 (4)	−0.0344 (4)	−0.1013 (3)	0.0692 (16)
H50	0.0556	−0.0192	−0.1506	0.083*
C46	0.2036 (4)	0.2492 (4)	−0.0146 (4)	0.0782 (18)
H46	0.1961	0.2690	−0.0618	0.094*
C45	0.2375 (4)	0.3014 (4)	0.0446 (5)	0.0816 (19)
H45	0.2527	0.3568	0.0368	0.098*
C51	0.0489 (4)	−0.1116 (5)	−0.0843 (4)	0.0778 (18)
H51	0.0186	−0.1496	−0.1217	0.093*
C43	0.2324 (4)	0.1936 (3)	0.1302 (3)	0.0612 (14)
H43	0.2434	0.1748	0.1782	0.073*
C44	0.2503 (4)	0.2746 (4)	0.1170 (4)	0.0790 (18)
H44	0.2711	0.3127	0.1559	0.095*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.067 (3)	0.045 (2)	0.078 (3)	−0.007 (2)	0.022 (2)	0.0049 (19)
O2	0.044 (2)	0.092 (3)	0.066 (2)	−0.005 (2)	0.0034 (19)	−0.008 (2)
O3	0.049 (2)	0.071 (2)	0.0386 (18)	0.0099 (18)	0.0089 (16)	0.0062 (16)
O4	0.063 (2)	0.077 (3)	0.057 (2)	0.0105 (19)	0.0297 (19)	0.0213 (19)
C8	0.050 (3)	0.038 (3)	0.038 (3)	−0.003 (2)	0.012 (2)	−0.004 (2)
C14	0.060 (3)	0.039 (3)	0.041 (3)	0.017 (2)	0.017 (3)	0.002 (2)
C2	0.050 (3)	0.047 (3)	0.035 (2)	0.007 (2)	0.012 (2)	−0.003 (2)
C7	0.041 (3)	0.035 (2)	0.033 (2)	−0.005 (2)	0.011 (2)	0.000 (2)
C1	0.045 (3)	0.039 (3)	0.033 (2)	0.005 (2)	0.006 (2)	0.000 (2)
C11	0.054 (3)	0.071 (3)	0.031 (3)	−0.016 (3)	0.013 (2)	0.002 (2)
C9	0.057 (3)	0.051 (3)	0.049 (3)	0.002 (2)	0.017 (3)	−0.007 (2)
C12	0.049 (3)	0.046 (3)	0.045 (3)	−0.006 (2)	0.011 (2)	0.004 (2)
C6	0.056 (3)	0.050 (3)	0.053 (3)	0.004 (3)	0.009 (3)	−0.003 (3)
C10	0.052 (3)	0.072 (4)	0.043 (3)	−0.015 (3)	0.022 (3)	−0.011 (3)
C13	0.058 (3)	0.058 (3)	0.045 (3)	0.001 (3)	0.028 (3)	0.003 (3)
C3	0.058 (3)	0.072 (4)	0.046 (3)	0.023 (3)	0.010 (3)	−0.006 (3)
C5	0.077 (4)	0.052 (3)	0.068 (4)	0.007 (3)	0.001 (3)	−0.020 (3)
C4	0.069 (4)	0.083 (5)	0.060 (4)	0.029 (4)	0.006 (3)	−0.021 (3)
O7	0.054 (2)	0.069 (3)	0.058 (2)	0.006 (2)	0.0176 (19)	0.0089 (19)
O5	0.073 (3)	0.054 (2)	0.052 (2)	0.010 (2)	−0.004 (2)	−0.004 (2)
O6A	0.125 (11)	0.067 (8)	0.083 (8)	0.037 (8)	−0.017 (7)	−0.015 (6)
O6B	0.118 (11)	0.047 (6)	0.084 (8)	−0.025 (7)	−0.040 (7)	0.035 (6)
C15	0.040 (3)	0.063 (3)	0.035 (3)	0.001 (2)	0.013 (2)	−0.006 (2)
C21	0.043 (3)	0.049 (3)	0.034 (2)	0.008 (2)	0.005 (2)	0.009 (2)
C16	0.043 (3)	0.049 (3)	0.039 (3)	−0.002 (2)	0.011 (2)	0.004 (2)
C22	0.055 (3)	0.049 (3)	0.045 (3)	0.008 (3)	0.009 (3)	0.008 (2)
C26	0.048 (3)	0.060 (4)	0.061 (3)	0.007 (3)	0.014 (3)	0.011 (3)
C17	0.068 (4)	0.053 (3)	0.056 (3)	−0.003 (3)	0.015 (3)	−0.006 (3)
C28	0.070 (4)	0.064 (4)	0.049 (3)	0.016 (3)	0.020 (3)	−0.002 (3)
C19	0.048 (3)	0.093 (5)	0.062 (4)	0.000 (3)	0.007 (3)	−0.025 (4)
C18	0.070 (4)	0.077 (4)	0.067 (4)	−0.022 (3)	0.023 (3)	−0.029 (3)
O8	0.094 (3)	0.081 (3)	0.177 (5)	0.035 (3)	0.079 (3)	0.014 (3)
C20	0.051 (3)	0.076 (4)	0.061 (3)	0.016 (3)	0.015 (3)	−0.010 (3)
C27	0.082 (4)	0.043 (3)	0.049 (3)	0.002 (3)	0.007 (3)	−0.003 (3)
C23	0.080 (4)	0.047 (3)	0.056 (3)	0.009 (3)	0.009 (3)	0.006 (3)
C24	0.092 (5)	0.045 (3)	0.072 (4)	0.004 (3)	0.009 (4)	0.007 (3)
C25	0.066 (4)	0.062 (4)	0.081 (4)	−0.006 (3)	0.010 (3)	0.030 (3)
N1	0.041 (2)	0.047 (2)	0.045 (2)	−0.0024 (19)	0.0120 (19)	−0.0049 (19)
C41	0.030 (2)	0.052 (3)	0.047 (3)	−0.006 (2)	0.011 (2)	−0.005 (2)
C36	0.031 (2)	0.055 (3)	0.048 (3)	−0.002 (2)	0.006 (2)	−0.006 (3)
C29	0.037 (3)	0.046 (3)	0.051 (3)	0.003 (2)	0.015 (2)	0.000 (2)
C35	0.039 (3)	0.069 (4)	0.046 (3)	0.004 (3)	0.003 (2)	0.001 (3)
C34	0.030 (2)	0.055 (3)	0.054 (3)	0.009 (2)	0.010 (2)	0.007 (3)
C40	0.050 (3)	0.058 (3)	0.055 (3)	−0.015 (3)	0.018 (3)	−0.003 (3)
C30	0.063 (3)	0.051 (3)	0.057 (3)	−0.001 (3)	0.016 (3)	−0.003 (3)
C37	0.051 (3)	0.076 (4)	0.054 (3)	0.000 (3)	0.010 (3)	−0.009 (3)
C38	0.052 (3)	0.070 (4)	0.075 (4)	−0.019 (3)	0.015 (3)	−0.026 (3)
C33	0.053 (3)	0.071 (4)	0.058 (3)	0.014 (3)	0.015 (3)	0.021 (3)
C39	0.055 (3)	0.058 (4)	0.083 (4)	−0.016 (3)	0.015 (3)	−0.003 (3)
C32	0.068 (4)	0.046 (3)	0.096 (5)	0.010 (3)	0.027 (4)	0.020 (3)
C31	0.073 (4)	0.044 (3)	0.092 (5)	0.000 (3)	0.024 (4)	−0.003 (3)
N2	0.048 (2)	0.048 (2)	0.042 (2)	0.0013 (19)	0.0162 (19)	0.0055 (19)
C54	0.032 (2)	0.053 (3)	0.039 (3)	0.008 (2)	0.008 (2)	0.000 (2)
C53	0.046 (3)	0.050 (3)	0.057 (3)	0.007 (2)	0.011 (3)	0.000 (3)
C42	0.037 (3)	0.049 (3)	0.061 (3)	0.003 (2)	0.016 (2)	0.013 (3)
C49	0.031 (2)	0.073 (4)	0.043 (3)	0.002 (2)	0.012 (2)	−0.005 (3)
C48	0.044 (3)	0.093 (4)	0.044 (3)	0.013 (3)	0.013 (3)	0.027 (3)
C47	0.037 (3)	0.061 (3)	0.067 (4)	0.008 (3)	0.014 (3)	0.018 (3)
C52	0.046 (3)	0.053 (3)	0.098 (5)	0.000 (3)	0.024 (3)	−0.014 (3)
C50	0.049 (3)	0.106 (5)	0.055 (3)	0.010 (4)	0.019 (3)	−0.014 (4)
C46	0.061 (4)	0.079 (4)	0.094 (5)	0.014 (4)	0.025 (4)	0.038 (4)
C45	0.055 (4)	0.059 (4)	0.122 (6)	0.001 (3)	0.018 (4)	0.023 (4)
C51	0.055 (4)	0.096 (5)	0.075 (5)	0.002 (4)	0.012 (3)	−0.040 (4)
C43	0.057 (3)	0.056 (4)	0.065 (4)	−0.004 (3)	0.012 (3)	−0.004 (3)
C44	0.064 (4)	0.059 (4)	0.102 (5)	0.004 (3)	0.010 (4)	−0.002 (4)

Geometric parameters (Å, º) top

O1—C13	1.325 (6)	C24—C25	1.382 (8)
O1—H01	0.84 (5)	C24—H24	0.9300
O2—C13	1.205 (6)	C25—H25	0.9300
O3—C14	1.265 (5)	N1—C41	1.355 (5)
O4—C14	1.246 (5)	N1—C29	1.357 (5)
C8—C7	1.391 (6)	C41—C40	1.405 (6)
C8—C9	1.404 (6)	C41—C36	1.424 (6)
C8—C14	1.500 (6)	C36—C35	1.364 (6)
C2—C3	1.381 (6)	C36—C37	1.420 (7)
C2—C1	1.393 (6)	C29—C34	1.417 (6)
C2—C13	1.495 (6)	C29—C30	1.423 (6)
C7—C12	1.393 (6)	C35—C34	1.389 (6)
C7—C1	1.497 (6)	C35—H35	0.9300
C1—C6	1.393 (6)	C34—C33	1.415 (7)
C11—C10	1.351 (7)	C40—C39	1.350 (7)
C11—C12	1.369 (6)	C40—H40	0.9300
C11—H11	0.9300	C30—C31	1.366 (7)
C9—C10	1.371 (6)	C30—H30	0.9300
C9—H9	0.9300	C37—C38	1.349 (7)
C12—H12	0.9300	C37—H37	0.9300
C6—C5	1.385 (7)	C38—C39	1.390 (7)
C6—H6	0.9300	C38—H38	0.9300
C10—H10	0.9300	C33—C32	1.340 (7)
C3—C4	1.364 (7)	C33—H33	0.9300
C3—H3	0.9300	C39—H39	0.9300
C5—C4	1.356 (8)	C32—C31	1.406 (7)
C5—H5	0.9300	C32—H32	0.9300
C4—H4	0.9300	C31—H31	0.9300
O7—C28	1.308 (6)	N2—C54	1.354 (5)
O7—H03	0.85 (5)	N2—C42	1.355 (6)
O5—C27	1.287 (6)	N2—H2	0.8600
O5—H02	0.84 (5)	C54—C49	1.400 (6)
O6A—C27	1.297 (12)	C54—C53	1.400 (6)
O6B—C27	1.223 (11)	C53—C52	1.350 (7)
C15—C16	1.381 (6)	C53—H53	0.9300
C15—C20	1.415 (6)	C42—C47	1.408 (7)
C15—C21	1.489 (6)	C42—C43	1.423 (7)
C21—C26	1.385 (6)	C49—C48	1.399 (7)
C21—C22	1.394 (6)	C49—C50	1.411 (7)
C16—C17	1.402 (6)	C48—C47	1.377 (7)
C16—C27	1.487 (7)	C48—H48	0.9300
C22—C23	1.392 (7)	C47—C46	1.436 (8)
C22—C28	1.505 (7)	C52—C51	1.412 (8)
C26—C25	1.369 (7)	C52—H52	0.9300
C26—H26	0.9300	C50—C51	1.330 (8)
C17—C18	1.373 (7)	C50—H50	0.9300
C17—H17	0.9300	C46—C45	1.360 (8)
C28—O8	1.199 (6)	C46—H46	0.9300
C19—C18	1.371 (7)	C45—C44	1.406 (8)
C19—C20	1.375 (7)	C45—H45	0.9300
C19—H19	0.9300	C51—H51	0.9300
C18—H18	0.9300	C43—C44	1.352 (7)
C20—H20	0.9300	C43—H43	0.9300
C23—C24	1.367 (7)	C44—H44	0.9300
C23—H23	0.9300

C13—O1—H01	113 (5)	C25—C24—H24	120.5
C7—C8—C9	118.8 (4)	C26—C25—C24	120.2 (5)
C7—C8—C14	122.3 (4)	C26—C25—H25	119.9
C9—C8—C14	118.9 (4)	C24—C25—H25	119.9
O4—C14—O3	123.6 (4)	C41—N1—C29	118.6 (4)
O4—C14—C8	118.4 (4)	N1—C41—C40	119.0 (4)
O3—C14—C8	118.0 (4)	N1—C41—C36	121.7 (4)
C3—C2—C1	120.2 (5)	C40—C41—C36	119.3 (4)
C3—C2—C13	117.7 (4)	C35—C36—C37	123.6 (5)
C1—C2—C13	122.1 (4)	C35—C36—C41	118.2 (4)
C8—C7—C12	118.6 (4)	C37—C36—C41	118.2 (5)
C8—C7—C1	122.7 (4)	N1—C29—C34	122.6 (4)
C12—C7—C1	118.4 (4)	N1—C29—C30	117.6 (4)
C2—C1—C6	118.5 (4)	C34—C29—C30	119.8 (4)
C2—C1—C7	123.3 (4)	C36—C35—C34	121.8 (5)
C6—C1—C7	117.9 (4)	C36—C35—H35	119.1
C10—C11—C12	120.0 (4)	C34—C35—H35	119.1
C10—C11—H11	120.0	C35—C34—C33	124.1 (5)
C12—C11—H11	120.0	C35—C34—C29	117.1 (4)
C10—C9—C8	120.5 (5)	C33—C34—C29	118.9 (5)
C10—C9—H9	119.8	C39—C40—C41	119.8 (5)
C8—C9—H9	119.8	C39—C40—H40	120.1
C11—C12—C7	121.4 (4)	C41—C40—H40	120.1
C11—C12—H12	119.3	C31—C30—C29	118.5 (5)
C7—C12—H12	119.3	C31—C30—H30	120.7
C5—C6—C1	119.9 (5)	C29—C30—H30	120.7
C5—C6—H6	120.0	C38—C37—C36	120.7 (5)
C1—C6—H6	120.0	C38—C37—H37	119.6
C11—C10—C9	120.7 (5)	C36—C37—H37	119.6
C11—C10—H10	119.7	C37—C38—C39	120.2 (5)
C9—C10—H10	119.7	C37—C38—H38	119.9
O2—C13—O1	121.1 (5)	C39—C38—H38	119.9
O2—C13—C2	123.2 (5)	C32—C33—C34	120.5 (5)
O1—C13—C2	115.8 (4)	C32—C33—H33	119.7
C4—C3—C2	120.3 (5)	C34—C33—H33	119.7
C4—C3—H3	119.8	C40—C39—C38	121.8 (5)
C2—C3—H3	119.8	C40—C39—H39	119.1
C4—C5—C6	120.6 (5)	C38—C39—H39	119.1
C4—C5—H5	119.7	C33—C32—C31	120.8 (5)
C6—C5—H5	119.7	C33—C32—H32	119.6
C5—C4—C3	120.5 (5)	C31—C32—H32	119.6
C5—C4—H4	119.8	C30—C31—C32	121.5 (5)
C3—C4—H4	119.8	C30—C31—H31	119.3
C28—O7—H03	116 (4)	C32—C31—H31	119.3
C27—O5—H02	112 (6)	C54—N2—C42	123.5 (4)
C16—C15—C20	117.5 (4)	C54—N2—H2	118.2
C16—C15—C21	125.8 (4)	C42—N2—H2	118.2
C20—C15—C21	116.7 (4)	N2—C54—C49	119.0 (4)
C26—C21—C22	117.4 (5)	N2—C54—C53	119.8 (4)
C26—C21—C15	119.6 (4)	C49—C54—C53	121.2 (5)
C22—C21—C15	122.8 (4)	C52—C53—C54	118.7 (5)
C15—C16—C17	119.7 (4)	C52—C53—H53	120.7
C15—C16—C27	124.9 (4)	C54—C53—H53	120.7
C17—C16—C27	115.3 (4)	N2—C42—C47	118.6 (5)
C23—C22—C21	120.2 (5)	N2—C42—C43	119.4 (4)
C23—C22—C28	115.9 (5)	C47—C42—C43	122.0 (5)
C21—C22—C28	123.8 (5)	C48—C49—C54	118.6 (5)
C25—C26—C21	122.1 (5)	C48—C49—C50	123.8 (5)
C25—C26—H26	118.9	C54—C49—C50	117.6 (5)
C21—C26—H26	118.9	C47—C48—C49	121.0 (4)
C18—C17—C16	121.1 (5)	C47—C48—H48	119.5
C18—C17—H17	119.5	C49—C48—H48	119.5
C16—C17—H17	119.5	C48—C47—C42	119.1 (5)
O8—C28—O7	122.9 (5)	C48—C47—C46	124.1 (5)
O8—C28—C22	123.5 (5)	C42—C47—C46	116.8 (5)
O7—C28—C22	113.6 (5)	C53—C52—C51	121.0 (5)
C18—C19—C20	118.7 (5)	C53—C52—H52	119.5
C18—C19—H19	120.6	C51—C52—H52	119.5
C20—C19—H19	120.6	C51—C50—C49	121.2 (6)
C19—C18—C17	120.5 (5)	C51—C50—H50	119.4
C19—C18—H18	119.8	C49—C50—H50	119.4
C17—C18—H18	119.8	C45—C46—C47	119.7 (6)
C19—C20—C15	122.5 (5)	C45—C46—H46	120.1
C19—C20—H20	118.7	C47—C46—H46	120.1
C15—C20—H20	118.7	C46—C45—C44	122.3 (6)
O6B—C27—O5	117.8 (7)	C46—C45—H45	118.8
O6B—C27—O6A	47.9 (6)	C44—C45—H45	118.8
O5—C27—O6A	114.3 (8)	C50—C51—C52	120.3 (5)
O6B—C27—C16	118.5 (7)	C50—C51—H51	119.9
O5—C27—C16	117.3 (5)	C52—C51—H51	119.9
O6A—C27—C16	123.0 (7)	C44—C43—C42	118.9 (5)
C24—C23—C22	121.1 (5)	C44—C43—H43	120.5
C24—C23—H23	119.4	C42—C43—H43	120.5
C22—C23—H23	119.4	C43—C44—C45	120.1 (6)
C23—C24—C25	118.9 (5)	C43—C44—H44	120.0
C23—C24—H24	120.5	C45—C44—H44	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O4	0.84	1.74	2.578 (6)	178
O7—H03···O3	0.85	1.75	2.596 (5)	173
O5—H02···N1ⁱ	0.84	1.86	2.675 (5)	162
C40—H40···O6Aⁱⁱ	0.93	2.39	3.258 (14)	155
C40—H40···O6Bⁱⁱ	0.93	2.57	3.282 (12)	133
N2—H2···O3ⁱⁱⁱ	0.86	1.88	2.734 (5)	177

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀O₄·C₁₄H₉O₄⁻·C₁₃H₉N·C₁₃H₁₀N⁺
M_r	842.86
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	14.461 (3), 15.863 (3), 19.166 (3)
β (°)	108.98 (2)
V (Å³)	4157.5 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7509, 7275, 3160
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.211, 1.01
No. of reflections	7275
No. of parameters	598
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)	0.23, −0.25

Computer programs: CAD-4 Software (Enraf-Nonius, 1988), CAD-4 Software (SETANG), TEXSAN(Molecular Structure Corporation, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1993), SHELXL97).

Selected bond lengths (Å) top

O1—C13	1.325 (6)	O5—C27	1.287 (6)
O2—C13	1.205 (6)	O6A—C27	1.297 (12)
O3—C14	1.265 (5)	O6B—C27	1.223 (11)
O4—C14	1.246 (5)	C28—O8	1.199 (6)
O7—C28	1.308 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O4	0.84	1.74	2.578 (6)	178
O7—H03···O3	0.85	1.75	2.596 (5)	173
O5—H02···N1ⁱ	0.84	1.86	2.675 (5)	162
C40—H40···O6Aⁱⁱ	0.93	2.39	3.258 (14)	155
C40—H40···O6Bⁱⁱ	0.93	2.57	3.282 (12)	133
N2—H2···O3ⁱⁱⁱ	0.86	1.88	2.734 (5)	177

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

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page