Terephthalic acid–2,2′-dimethyl-1,1′-(butane-1,4-di­yl)dibenzimidazole (2/3)

Jiang, H.; Dong, X.-W.

doi:10.1107/S1600536808009665

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o838

doi:10.1107/S1600536808009665

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Terephthalic acid–2,2′-dimethyl-1,1′-(butane-1,4-diyl)dibenzimidazole (2/3)

Hui Jiang ^a and Xian-Wu Dong ^a ^*

^aDepartment of Chemistry, Jilin Agriculture Science and Technology College, Jilin 132101, People's Republic of China
^*Correspondence e-mail: jiangh_468@yahoo.com.cn

(Received 22 November 2007; accepted 8 April 2008; online 16 April 2008)

In the crystal structure of the title compound, 2C₈H₆O₄·3C₂₀H₂₂N₄, there are three independent 2,2′-dimethyl-1,1′-(butane-1,4-diyl)dibenzimidazole molecules, each of which lies on an inversion centre. The terephthalic acid molecules are linked to adjacent 2,2′-dimethyl-1,1′-(butane-1,4-diyl)dibenzimidazole molecules via O—H⋯N hydrogen bonds.

Related literature

For related literature, see: Dale & Elsegood (2004 ); Ma et al. (2000 ).

Experimental

Crystal data

2C₈H₆O₄·3C₂₀H₂₂N₄
M_r = 1286.88
Triclinic, $[P \overline 1]$
a = 9.225 (5) Å
b = 12.298 (8) Å
c = 14.883 (7) Å
α = 87.17 (2)°
β = 87.768 (16)°
γ = 89.33 (2)°
V = 1685.0 (16) Å³
Z = 1
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.49 × 0.38 × 0.26 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.963, T_max = 0.977
16449 measured reflections
7573 independent reflections
3739 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.163
S = 1.01
7573 reflections
437 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	1.83	2.609 (3)	157
O3—H3A⋯N3ⁱⁱ	0.82	1.87	2.668 (3)	165
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y-1, z.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009665/cs2066sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009665/cs2066Isup2.hkl

checkCIF report

Comment top

The title compound is composed of terephthalic acid and 2,2'-dimethyl-1,1'-(butane-1,4-diyl)dibenzimidazole (Fig. 1). The bond distances and angles are normal (Dale & Elsegood, 2004; Ma et al., 2000). There are three independent 2,2'-dimethyl-1,1'-(butane-1,4-diyl)dibenzimidazole molecules, which extend in different directions, sitting around independent symmetry centres. The terephthalic acids are hydrogen bonded to the 2,2'-dimethyl-1,1'-(butane-1,4-diyl)dibenzimidazole (Table 1) via O—H···N hydrogen bonds into the chains (Fig. 2).

Related literature top

For related literature, see: Dale & Elsegood (2004); Ma et al. (2000).

Experimental top

A mixture of terephthalic acid (0.033 g, 0.2 mmol), 2,2'-dimethyl-1,1'-(butane-1,4-diyl)dibenzimidazole (0.064 g, 0.2 mmol) in 1:4 (v/v) EtOH/H₂O (10 ml) was placed in a Teflon-lined autoclave. The mixture was heated at 430 K for 1 days, and then it was gradually cooled to room temperature at a rate of 10 K.h^-1. Colorless single crystals of the title compound were obtained.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title clathrate. The displacement ellipsoids are drawn at the 30% probability level.(i) -x, -y, -z + 1. (ii) -x, -y + 1, -z + 1. (iii) -x + 1, -y + 1, -z. (iv) -x + 2, -y, -z.
	Fig. 2. A one-dimensional chain linked by hydrogen bonds. The H-bonds are shown as dashed lines.

Terephthalic acid–2,2'-dimethyl-1,1'-(butane-1,4-diyl)dibenzimidazole (2/3) top

Crystal data top

2C₈H₆O₄·3C₂₀H₂₂N₄	Z = 1
M_r = 1286.88	F(000) = 682
Triclinic, P1	D_x = 1.268 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.225 (5) Å	Cell parameters from 7573 reflections
b = 12.298 (8) Å	θ = 3.0–27.5°
c = 14.883 (7) Å	µ = 0.08 mm⁻¹
α = 87.17 (2)°	T = 293 K
β = 87.768 (16)°	Plate, colourless
γ = 89.33 (2)°	0.49 × 0.38 × 0.26 mm
V = 1685.0 (16) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	7573 independent reflections
Radiation source: rotation-anode tube	3739 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −11→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
T_min = 0.963, T_max = 0.977	l = −19→19
16449 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.071	H-atom parameters constrained
wR(F²) = 0.163	w = 1/[σ²(F_o²) + (0.0674P)² + 0.1144P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
7573 reflections	Δρ_max = 0.23 e Å⁻³
437 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0101 (15)

Crystal data top

2C₈H₆O₄·3C₂₀H₂₂N₄	γ = 89.33 (2)°
M_r = 1286.88	V = 1685.0 (16) Å³
Triclinic, P1	Z = 1
a = 9.225 (5) Å	Mo Kα radiation
b = 12.298 (8) Å	µ = 0.08 mm⁻¹
c = 14.883 (7) Å	T = 293 K
α = 87.17 (2)°	0.49 × 0.38 × 0.26 mm
β = 87.768 (16)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	7573 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3739 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.977	R_int = 0.055
16449 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
7573 reflections	Δρ_min = −0.21 e Å⁻³
437 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.4952 (3)	0.6452 (2)	0.39701 (16)	0.0443 (6)
C2	0.4004 (3)	0.5588 (2)	0.41249 (16)	0.0436 (6)
C3	0.4031 (3)	0.4701 (2)	0.35876 (18)	0.0565 (7)
H3	0.3405	0.4119	0.3701	0.068*
C4	0.5025 (4)	0.4726 (3)	0.2882 (2)	0.0728 (10)
H4	0.5074	0.4144	0.2505	0.087*
C5	0.5956 (4)	0.5585 (3)	0.2710 (2)	0.0713 (9)
H5	0.6609	0.5570	0.2218	0.086*
C6	0.5948 (3)	0.6460 (3)	0.32422 (18)	0.0592 (8)
H6	0.6581	0.7037	0.3123	0.071*
C7	0.3629 (3)	0.6799 (2)	0.51495 (18)	0.0481 (7)
C8	0.2974 (3)	0.7342 (3)	0.5937 (2)	0.0756 (10)
H8A	0.3136	0.6901	0.6475	0.113*
H8B	0.1949	0.7435	0.5864	0.113*
H8C	0.3410	0.8041	0.5982	0.113*
C9	0.9763 (2)	0.4712 (2)	0.16737 (16)	0.0383 (6)
C10	0.8777 (2)	0.4183 (2)	0.11664 (15)	0.0368 (6)
C11	0.8522 (3)	0.3085 (2)	0.12836 (18)	0.0521 (7)
H11	0.7845	0.2741	0.0951	0.063*
C12	0.9318 (3)	0.2525 (2)	0.1917 (2)	0.0611 (8)
H12	0.9170	0.1782	0.2021	0.073*
C13	1.0343 (3)	0.3039 (3)	0.24080 (18)	0.0621 (8)
H13	1.0883	0.2627	0.2819	0.074*
C14	1.0571 (3)	0.4128 (2)	0.22996 (17)	0.0529 (7)
H14	1.1247	0.4469	0.2635	0.063*
C15	0.8801 (2)	0.5945 (2)	0.08040 (16)	0.0416 (6)
C16	0.8408 (3)	0.7004 (2)	0.0362 (2)	0.0604 (8)
H16A	0.8748	0.7024	−0.0256	0.091*
H16B	0.8848	0.7580	0.0664	0.091*
H16C	0.7373	0.7096	0.0392	0.091*
C17	0.1997 (2)	0.5149 (2)	0.52713 (18)	0.0519 (7)
H17A	0.1880	0.5270	0.5909	0.062*
H17B	0.2251	0.4388	0.5207	0.062*
C18	0.0580 (2)	0.5394 (2)	0.48259 (17)	0.0511 (7)
H18A	0.0717	0.5344	0.4180	0.061*
H18B	0.0269	0.6132	0.4944	0.061*
C19	0.7073 (2)	0.4862 (2)	−0.00500 (16)	0.0469 (7)
H19A	0.7158	0.4139	−0.0281	0.056*
H19B	0.7226	0.5386	−0.0553	0.056*
C20	0.5564 (2)	0.5015 (2)	0.03514 (15)	0.0410 (6)
H20A	0.5369	0.4444	0.0812	0.049*
H20B	0.5502	0.5708	0.0635	0.049*
C21	0.6099 (3)	0.0780 (2)	0.09565 (19)	0.0499 (7)
C22	0.5086 (3)	0.1624 (2)	0.08891 (18)	0.0463 (6)
C23	0.4243 (3)	0.1903 (3)	0.1628 (2)	0.0667 (8)
H23	0.3561	0.2464	0.1585	0.080*
C24	0.4434 (4)	0.1336 (4)	0.2417 (3)	0.0917 (12)
H24	0.3872	0.1516	0.2922	0.110*
C25	0.5439 (5)	0.0499 (4)	0.2497 (3)	0.0946 (13)
H25	0.5544	0.0133	0.3053	0.114*
C26	0.6290 (4)	0.0197 (3)	0.1766 (3)	0.0764 (10)
H26	0.6960	−0.0372	0.1814	0.092*
C27	0.6126 (3)	0.1528 (2)	−0.0416 (2)	0.0569 (7)
C28	0.6558 (4)	0.1745 (4)	−0.1375 (2)	0.0991 (13)
H28A	0.7523	0.2031	−0.1420	0.149*
H28B	0.5899	0.2266	−0.1641	0.149*
H28C	0.6531	0.1081	−0.1685	0.149*
C29	0.7922 (3)	−0.0014 (3)	−0.0138 (3)	0.0739 (10)
H29A	0.7951	−0.0081	−0.0785	0.089*
H29B	0.7731	−0.0729	0.0143	0.089*
C30	0.9373 (3)	0.0365 (2)	0.0140 (3)	0.0741 (10)
H30A	0.9350	0.0407	0.0790	0.089*
H30B	0.9541	0.1093	−0.0121	0.089*
C31	0.1777 (3)	0.0473 (2)	0.42478 (16)	0.0420 (6)
C32	0.2506 (3)	−0.0499 (2)	0.41235 (17)	0.0493 (7)
H32	0.3417	−0.0616	0.4358	0.059*
C33	0.1875 (3)	−0.1296 (2)	0.36497 (17)	0.0490 (7)
H33	0.2373	−0.1947	0.3563	0.059*
C34	0.0517 (3)	−0.1139 (2)	0.33031 (16)	0.0449 (6)
C35	−0.0224 (3)	−0.0178 (2)	0.34588 (18)	0.0504 (7)
H35	−0.1151	−0.0069	0.3245	0.060*
C36	0.0403 (3)	0.0617 (2)	0.39292 (17)	0.0507 (7)
H36	−0.0107	0.1258	0.4033	0.061*
C37	0.2471 (3)	0.1394 (2)	0.46745 (18)	0.0497 (7)
C38	−0.0130 (3)	−0.1938 (2)	0.27258 (19)	0.0518 (7)
N1	0.4693 (2)	0.72048 (18)	0.46235 (15)	0.0498 (6)
N2	0.3174 (2)	0.58270 (18)	0.48811 (13)	0.0442 (5)
N3	0.9751 (2)	0.58143 (17)	0.14404 (14)	0.0445 (5)
N4	0.81999 (19)	0.49945 (16)	0.05991 (13)	0.0393 (5)
N5	0.6745 (2)	0.07253 (18)	0.01097 (17)	0.0530 (6)
N6	0.5129 (2)	0.20832 (19)	0.00184 (15)	0.0567 (6)
O1	0.3721 (2)	0.11390 (16)	0.50186 (14)	0.0674 (6)
H1	0.4049	0.1675	0.5244	0.081*
O2	0.1950 (2)	0.22979 (17)	0.46676 (16)	0.0793 (7)
O3	0.0626 (2)	−0.28314 (16)	0.26517 (13)	0.0667 (6)
H3A	0.0214	−0.3237	0.2325	0.080*
O4	−0.1239 (2)	−0.17682 (18)	0.23391 (17)	0.0881 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0354 (13)	0.0509 (17)	0.0473 (14)	−0.0004 (12)	−0.0090 (12)	−0.0023 (12)
C2	0.0352 (13)	0.0505 (17)	0.0462 (14)	−0.0008 (12)	−0.0111 (12)	−0.0054 (12)
C3	0.0593 (17)	0.0555 (19)	0.0567 (17)	−0.0048 (14)	−0.0188 (15)	−0.0092 (14)
C4	0.086 (2)	0.082 (3)	0.0530 (18)	0.008 (2)	−0.0140 (18)	−0.0234 (17)
C5	0.067 (2)	0.101 (3)	0.0458 (16)	0.007 (2)	0.0036 (15)	−0.0110 (18)
C6	0.0447 (15)	0.077 (2)	0.0550 (17)	−0.0084 (14)	−0.0038 (14)	0.0042 (16)
C7	0.0386 (14)	0.0508 (18)	0.0563 (16)	0.0061 (13)	−0.0086 (13)	−0.0128 (13)
C8	0.073 (2)	0.083 (3)	0.073 (2)	0.0173 (18)	−0.0005 (18)	−0.0272 (18)
C9	0.0306 (12)	0.0401 (15)	0.0448 (13)	0.0012 (10)	−0.0050 (11)	−0.0063 (11)
C10	0.0303 (11)	0.0393 (15)	0.0413 (13)	0.0020 (10)	−0.0022 (11)	−0.0058 (11)
C11	0.0502 (15)	0.0467 (18)	0.0603 (16)	−0.0047 (13)	−0.0004 (14)	−0.0116 (13)
C12	0.074 (2)	0.0376 (17)	0.0702 (19)	0.0023 (15)	0.0017 (17)	0.0047 (14)
C13	0.0659 (19)	0.064 (2)	0.0545 (17)	0.0139 (16)	−0.0068 (15)	0.0121 (15)
C14	0.0465 (15)	0.062 (2)	0.0512 (15)	0.0058 (14)	−0.0139 (13)	−0.0031 (14)
C15	0.0321 (12)	0.0407 (15)	0.0520 (14)	−0.0006 (11)	−0.0035 (12)	−0.0019 (12)
C16	0.0524 (16)	0.0495 (18)	0.079 (2)	0.0006 (13)	−0.0095 (16)	0.0099 (15)
C17	0.0347 (13)	0.067 (2)	0.0529 (15)	−0.0090 (13)	−0.0040 (12)	0.0059 (13)
C18	0.0348 (13)	0.0659 (19)	0.0522 (15)	−0.0069 (12)	−0.0052 (12)	0.0051 (13)
C19	0.0336 (13)	0.0634 (19)	0.0452 (14)	−0.0010 (12)	−0.0112 (12)	−0.0094 (12)
C20	0.0348 (12)	0.0491 (16)	0.0399 (13)	−0.0020 (11)	−0.0075 (11)	−0.0051 (11)
C21	0.0346 (13)	0.0450 (17)	0.0704 (19)	−0.0064 (11)	−0.0049 (14)	−0.0025 (14)
C22	0.0335 (13)	0.0458 (16)	0.0601 (17)	−0.0004 (11)	−0.0031 (13)	−0.0071 (13)
C23	0.0556 (18)	0.074 (2)	0.071 (2)	0.0005 (16)	0.0074 (17)	−0.0108 (17)
C24	0.081 (3)	0.118 (4)	0.075 (3)	−0.013 (2)	0.014 (2)	−0.008 (2)
C25	0.092 (3)	0.117 (4)	0.073 (2)	−0.026 (3)	−0.008 (2)	0.029 (2)
C26	0.064 (2)	0.060 (2)	0.104 (3)	−0.0069 (16)	−0.018 (2)	0.021 (2)
C27	0.0495 (16)	0.0558 (19)	0.0654 (18)	−0.0039 (14)	0.0031 (15)	−0.0061 (15)
C28	0.099 (3)	0.130 (4)	0.068 (2)	−0.011 (3)	0.016 (2)	−0.008 (2)
C29	0.0360 (14)	0.053 (2)	0.135 (3)	0.0018 (13)	0.0092 (17)	−0.0380 (19)
C30	0.0364 (14)	0.053 (2)	0.135 (3)	−0.0005 (13)	0.0082 (17)	−0.0372 (19)
C31	0.0445 (14)	0.0370 (15)	0.0443 (14)	−0.0032 (11)	−0.0018 (12)	0.0001 (11)
C32	0.0450 (14)	0.0439 (17)	0.0599 (16)	0.0015 (12)	−0.0139 (13)	−0.0032 (13)
C33	0.0487 (15)	0.0383 (16)	0.0607 (16)	0.0024 (12)	−0.0113 (14)	−0.0041 (12)
C34	0.0452 (14)	0.0405 (15)	0.0488 (14)	−0.0043 (12)	−0.0051 (12)	0.0039 (12)
C35	0.0419 (14)	0.0489 (18)	0.0606 (16)	−0.0020 (12)	−0.0092 (13)	0.0005 (13)
C36	0.0465 (15)	0.0448 (17)	0.0608 (16)	0.0066 (12)	−0.0019 (14)	−0.0033 (13)
C37	0.0494 (15)	0.0449 (18)	0.0549 (16)	−0.0024 (13)	−0.0004 (14)	−0.0028 (13)
C38	0.0482 (15)	0.0445 (17)	0.0636 (17)	−0.0044 (13)	−0.0095 (14)	−0.0044 (13)
N1	0.0382 (12)	0.0499 (14)	0.0623 (14)	−0.0034 (10)	−0.0078 (11)	−0.0085 (11)
N2	0.0304 (10)	0.0540 (14)	0.0484 (12)	−0.0042 (10)	−0.0031 (10)	−0.0044 (10)
N3	0.0361 (11)	0.0408 (13)	0.0579 (13)	−0.0021 (9)	−0.0122 (10)	−0.0067 (10)
N4	0.0298 (10)	0.0412 (13)	0.0478 (11)	−0.0028 (9)	−0.0090 (9)	−0.0061 (9)
N5	0.0352 (11)	0.0444 (14)	0.0801 (16)	−0.0001 (10)	0.0049 (12)	−0.0153 (12)
N6	0.0486 (13)	0.0566 (16)	0.0644 (15)	0.0090 (11)	−0.0013 (12)	−0.0023 (12)
O1	0.0630 (12)	0.0492 (13)	0.0933 (15)	−0.0026 (10)	−0.0258 (12)	−0.0187 (10)
O2	0.0744 (14)	0.0431 (13)	0.1239 (19)	0.0057 (11)	−0.0263 (13)	−0.0218 (12)
O3	0.0662 (12)	0.0494 (13)	0.0883 (14)	0.0003 (10)	−0.0303 (11)	−0.0199 (11)
O4	0.0714 (14)	0.0772 (17)	0.1216 (19)	0.0137 (12)	−0.0481 (15)	−0.0336 (14)

Geometric parameters (Å, º) top

C1—N1	1.388 (3)	C20—C20ⁱⁱ	1.506 (4)
C1—C2	1.388 (4)	C20—H20A	0.9700
C1—C6	1.393 (4)	C20—H20B	0.9700
C2—N2	1.378 (3)	C21—N5	1.377 (3)
C2—C3	1.384 (4)	C21—C26	1.387 (4)
C3—C4	1.367 (4)	C21—C22	1.392 (3)
C3—H3	0.9300	C22—C23	1.377 (4)
C4—C5	1.377 (5)	C22—N6	1.387 (3)
C4—H4	0.9300	C23—C24	1.353 (5)
C5—C6	1.367 (4)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.381 (5)
C6—H6	0.9300	C24—H24	0.9300
C7—N1	1.319 (3)	C25—C26	1.380 (5)
C7—N2	1.355 (3)	C25—H25	0.9300
C7—C8	1.482 (4)	C26—H26	0.9300
C8—H8A	0.9600	C27—N6	1.308 (3)
C8—H8B	0.9600	C27—N5	1.363 (3)
C8—H8C	0.9600	C27—C28	1.479 (4)
C9—N3	1.382 (3)	C28—H28A	0.9600
C9—C14	1.384 (3)	C28—H28B	0.9600
C9—C10	1.391 (3)	C28—H28C	0.9600
C10—C11	1.375 (4)	C29—N5	1.456 (3)
C10—N4	1.390 (3)	C29—C30	1.502 (4)
C11—C12	1.371 (4)	C29—H29A	0.9700
C11—H11	0.9300	C29—H29B	0.9700
C12—C13	1.393 (4)	C30—C30ⁱⁱⁱ	1.515 (5)
C12—H12	0.9300	C30—H30A	0.9700
C13—C14	1.359 (4)	C30—H30B	0.9700
C13—H13	0.9300	C31—C36	1.377 (3)
C14—H14	0.9300	C31—C32	1.381 (3)
C15—N3	1.318 (3)	C31—C37	1.488 (4)
C15—N4	1.353 (3)	C32—C33	1.382 (4)
C15—C16	1.477 (4)	C32—H32	0.9300
C16—H16A	0.9600	C33—C34	1.382 (3)
C16—H16B	0.9600	C33—H33	0.9300
C16—H16C	0.9600	C34—C35	1.383 (4)
C17—N2	1.462 (3)	C34—C38	1.482 (4)
C17—C18	1.510 (3)	C35—C36	1.376 (4)
C17—H17A	0.9700	C35—H35	0.9300
C17—H17B	0.9700	C36—H36	0.9300
C18—C18ⁱ	1.511 (5)	C37—O2	1.206 (3)
C18—H18A	0.9700	C37—O1	1.308 (3)
C18—H18B	0.9700	C38—O4	1.205 (3)
C19—N4	1.463 (3)	C38—O3	1.301 (3)
C19—C20	1.507 (3)	O1—H1	0.8199
C19—H19A	0.9700	O3—H3A	0.8197
C19—H19B	0.9700

N1—C1—C2	109.2 (2)	N5—C21—C26	133.3 (3)
N1—C1—C6	130.6 (3)	N5—C21—C22	105.5 (2)
C2—C1—C6	120.2 (3)	C26—C21—C22	121.2 (3)
N2—C2—C3	132.0 (3)	C23—C22—N6	129.6 (2)
N2—C2—C1	105.9 (2)	C23—C22—C21	120.7 (3)
C3—C2—C1	122.1 (3)	N6—C22—C21	109.7 (2)
C4—C3—C2	116.5 (3)	C24—C23—C22	118.1 (3)
C4—C3—H3	121.8	C24—C23—H23	121.0
C2—C3—H3	121.8	C22—C23—H23	121.0
C3—C4—C5	122.1 (3)	C23—C24—C25	122.0 (4)
C3—C4—H4	118.9	C23—C24—H24	119.0
C5—C4—H4	118.9	C25—C24—H24	119.0
C6—C5—C4	121.8 (3)	C26—C25—C24	121.1 (3)
C6—C5—H5	119.1	C26—C25—H25	119.4
C4—C5—H5	119.1	C24—C25—H25	119.4
C5—C6—C1	117.2 (3)	C25—C26—C21	117.0 (3)
C5—C6—H6	121.4	C25—C26—H26	121.5
C1—C6—H6	121.4	C21—C26—H26	121.5
N1—C7—N2	112.3 (2)	N6—C27—N5	113.0 (3)
N1—C7—C8	124.5 (3)	N6—C27—C28	124.1 (3)
N2—C7—C8	123.2 (3)	N5—C27—C28	122.9 (3)
C7—C8—H8A	109.5	C27—C28—H28A	109.5
C7—C8—H8B	109.5	C27—C28—H28B	109.5
H8A—C8—H8B	109.5	H28A—C28—H28B	109.5
C7—C8—H8C	109.5	C27—C28—H28C	109.5
H8A—C8—H8C	109.5	H28A—C28—H28C	109.5
H8B—C8—H8C	109.5	H28B—C28—H28C	109.5
N3—C9—C14	130.0 (2)	N5—C29—C30	112.6 (2)
N3—C9—C10	109.79 (19)	N5—C29—H29A	109.1
C14—C9—C10	120.2 (2)	C30—C29—H29A	109.1
C11—C10—N4	132.6 (2)	N5—C29—H29B	109.1
C11—C10—C9	122.3 (2)	C30—C29—H29B	109.1
N4—C10—C9	105.0 (2)	H29A—C29—H29B	107.8
C12—C11—C10	116.4 (2)	C29—C30—C30ⁱⁱⁱ	113.8 (3)
C12—C11—H11	121.8	C29—C30—H30A	108.8
C10—C11—H11	121.8	C30ⁱⁱⁱ—C30—H30A	108.8
C11—C12—C13	121.8 (3)	C29—C30—H30B	108.8
C11—C12—H12	119.1	C30ⁱⁱⁱ—C30—H30B	108.8
C13—C12—H12	119.1	H30A—C30—H30B	107.7
C14—C13—C12	121.4 (2)	C36—C31—C32	119.4 (2)
C14—C13—H13	119.3	C36—C31—C37	119.0 (2)
C12—C13—H13	119.3	C32—C31—C37	121.6 (2)
C13—C14—C9	117.8 (2)	C31—C32—C33	119.8 (2)
C13—C14—H14	121.1	C31—C32—H32	120.1
C9—C14—H14	121.1	C33—C32—H32	120.1
N3—C15—N4	112.5 (2)	C34—C33—C32	120.9 (2)
N3—C15—C16	124.6 (2)	C34—C33—H33	119.6
N4—C15—C16	122.9 (2)	C32—C33—H33	119.6
C15—C16—H16A	109.5	C33—C34—C35	118.8 (2)
C15—C16—H16B	109.5	C33—C34—C38	122.0 (2)
H16A—C16—H16B	109.5	C35—C34—C38	119.1 (2)
C15—C16—H16C	109.5	C36—C35—C34	120.3 (2)
H16A—C16—H16C	109.5	C36—C35—H35	119.8
H16B—C16—H16C	109.5	C34—C35—H35	119.8
N2—C17—C18	112.0 (2)	C35—C36—C31	120.7 (2)
N2—C17—H17A	109.2	C35—C36—H36	119.6
C18—C17—H17A	109.2	C31—C36—H36	119.6
N2—C17—H17B	109.2	O2—C37—O1	123.6 (3)
C18—C17—H17B	109.2	O2—C37—C31	122.7 (2)
H17A—C17—H17B	107.9	O1—C37—C31	113.7 (2)
C17—C18—C18ⁱ	110.9 (3)	O4—C38—O3	122.7 (3)
C17—C18—H18A	109.5	O4—C38—C34	123.2 (3)
C18ⁱ—C18—H18A	109.5	O3—C38—C34	114.1 (2)
C17—C18—H18B	109.5	C7—N1—C1	105.6 (2)
C18ⁱ—C18—H18B	109.5	C7—N2—C2	107.1 (2)
H18A—C18—H18B	108.0	C7—N2—C17	128.4 (2)
N4—C19—C20	112.81 (19)	C2—N2—C17	124.5 (2)
N4—C19—H19A	109.0	C15—N3—C9	105.54 (19)
C20—C19—H19A	109.0	C15—N4—C10	107.14 (18)
N4—C19—H19B	109.0	C15—N4—C19	126.2 (2)
C20—C19—H19B	109.0	C10—N4—C19	126.5 (2)
H19A—C19—H19B	107.8	C27—N5—C21	106.6 (2)
C20ⁱⁱ—C20—C19	111.6 (2)	C27—N5—C29	127.9 (3)
C20ⁱⁱ—C20—H20A	109.3	C21—N5—C29	125.4 (3)
C19—C20—H20A	109.3	C27—N6—C22	105.1 (2)
C20ⁱⁱ—C20—H20B	109.3	C37—O1—H1	109.3
C19—C20—H20B	109.3	C38—O3—H3A	109.4
H20A—C20—H20B	108.0

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1^iv	0.82	1.83	2.609 (3)	157
O3—H3A···N3^v	0.82	1.87	2.668 (3)	165

Symmetry codes: (iv) −x+1, −y+1, −z+1; (v) x−1, y−1, z.

Experimental details

Crystal data
Chemical formula	2C₈H₆O₄·3C₂₀H₂₂N₄
M_r	1286.88
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.225 (5), 12.298 (8), 14.883 (7)
α, β, γ (°)	87.17 (2), 87.768 (16), 89.33 (2)
V (Å³)	1685.0 (16)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.49 × 0.38 × 0.26

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.963, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	16449, 7573, 3739
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.163, 1.01
No. of reflections	7573
No. of parameters	437
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	1.83	2.609 (3)	157.1
O3—H3A···N3ⁱⁱ	0.82	1.87	2.668 (3)	165.2

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

Acknowledgements

The authors thank the Analysis and Testing Foundation of Northeast Normal University for support.

References

Dale, S. H. & Elsegood, M. R. J. (2004). Acta Cryst. C60, o444–o448. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Ma, J.-F., Liu, J.-F., Liu, Y.-C., Xing, Y., Jia, H.-Q. & Lin, Y.-H. (2000). New J. Chem. 24, 759–763. Web of Science CrossRef CAS Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar