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Acta Cryst. (2008). E64, o838    [ doi:10.1107/S1600536808009665 ]

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

H. Jiang and X.-W. Dong

Abstract top

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.

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.

Refinement top

All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93 Å, Uiso = 1.2Ueq (C) for aromatic, 0.97 Å, Uiso = 1.5Ueq (C) for CH2 atoms and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms. Hydroxyl H atoms were refined using a riding model with d(O—H) = 0.82 Å, Uiso = 1.5Ueq (O).

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
[Figure 1] 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.
[Figure 2] 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
2C8H6O4·3C20H22N4Z = 1
Mr = 1286.88F000 = 682
Triclinic, P1Dx = 1.268 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71069 Å
a = 9.225 (5) ÅCell parameters from 7573 reflections
b = 12.298 (8) Åθ = 3.0–27.5º
c = 14.883 (7) ŵ = 0.08 mm−1
α = 87.17 (2)ºT = 293 (2) K
β = 87.768 (16)ºPlate, colourless
γ = 89.33 (2)º0.49 × 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 tube3739 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.055
Detector resolution: 10.0 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.0º
ω scansh = −11→10
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −15→15
Tmin = 0.963, Tmax = 0.977l = −19→19
16449 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.071  w = 1/[σ2(Fo2) + (0.0674P)2 + 0.1144P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.163(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.23 e Å−3
7573 reflectionsΔρmin = −0.21 e Å−3
437 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0101 (15)
Secondary atom site location: difference Fourier map
Crystal data top
2C8H6O4·3C20H22N4γ = 89.33 (2)º
Mr = 1286.88V = 1685.0 (16) Å3
Triclinic, P1Z = 1
a = 9.225 (5) ÅMo Kα
b = 12.298 (8) ŵ = 0.08 mm−1
c = 14.883 (7) ÅT = 293 (2) K
α = 87.17 (2)º0.49 × 0.38 × 0.26 mm
β = 87.768 (16)º
Data collection top
Rigaku R-AXIS RAPID
diffractometer		7573 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		3739 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.977Rint = 0.055
16449 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.071437 parameters
wR(F2) = 0.163H-atom parameters constrained
S = 1.01Δρmax = 0.23 e Å−3
7573 reflectionsΔρmin = −0.21 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4952 (3)0.6452 (2)0.39701 (16)0.0443 (6)
C20.4004 (3)0.5588 (2)0.41249 (16)0.0436 (6)
C30.4031 (3)0.4701 (2)0.35876 (18)0.0565 (7)
H30.34050.41190.37010.068*
C40.5025 (4)0.4726 (3)0.2882 (2)0.0728 (10)
H40.50740.41440.25050.087*
C50.5956 (4)0.5585 (3)0.2710 (2)0.0713 (9)
H50.66090.55700.22180.086*
C60.5948 (3)0.6460 (3)0.32422 (18)0.0592 (8)
H60.65810.70370.31230.071*
C70.3629 (3)0.6799 (2)0.51495 (18)0.0481 (7)
C80.2974 (3)0.7342 (3)0.5937 (2)0.0756 (10)
H8A0.31360.69010.64750.113*
H8B0.19490.74350.58640.113*
H8C0.34100.80410.59820.113*
C90.9763 (2)0.4712 (2)0.16737 (16)0.0383 (6)
C100.8777 (2)0.4183 (2)0.11664 (15)0.0368 (6)
C110.8522 (3)0.3085 (2)0.12836 (18)0.0521 (7)
H110.78450.27410.09510.063*
C120.9318 (3)0.2525 (2)0.1917 (2)0.0611 (8)
H120.91700.17820.20210.073*
C131.0343 (3)0.3039 (3)0.24080 (18)0.0621 (8)
H131.08830.26270.28190.074*
C141.0571 (3)0.4128 (2)0.22996 (17)0.0529 (7)
H141.12470.44690.26350.063*
C150.8801 (2)0.5945 (2)0.08040 (16)0.0416 (6)
C160.8408 (3)0.7004 (2)0.0362 (2)0.0604 (8)
H16A0.87480.7024−0.02560.091*
H16B0.88480.75800.06640.091*
H16C0.73730.70960.03920.091*
C170.1997 (2)0.5149 (2)0.52713 (18)0.0519 (7)
H17A0.18800.52700.59090.062*
H17B0.22510.43880.52070.062*
C180.0580 (2)0.5394 (2)0.48259 (17)0.0511 (7)
H18A0.07170.53440.41800.061*
H18B0.02690.61320.49440.061*
C190.7073 (2)0.4862 (2)−0.00500 (16)0.0469 (7)
H19A0.71580.4139−0.02810.056*
H19B0.72260.5386−0.05530.056*
C200.5564 (2)0.5015 (2)0.03514 (15)0.0410 (6)
H20A0.53690.44440.08120.049*
H20B0.55020.57080.06350.049*
C210.6099 (3)0.0780 (2)0.09565 (19)0.0499 (7)
C220.5086 (3)0.1624 (2)0.08891 (18)0.0463 (6)
C230.4243 (3)0.1903 (3)0.1628 (2)0.0667 (8)
H230.35610.24640.15850.080*
C240.4434 (4)0.1336 (4)0.2417 (3)0.0917 (12)
H240.38720.15160.29220.110*
C250.5439 (5)0.0499 (4)0.2497 (3)0.0946 (13)
H250.55440.01330.30530.114*
C260.6290 (4)0.0197 (3)0.1766 (3)0.0764 (10)
H260.6960−0.03720.18140.092*
C270.6126 (3)0.1528 (2)−0.0416 (2)0.0569 (7)
C280.6558 (4)0.1745 (4)−0.1375 (2)0.0991 (13)
H28A0.75230.2031−0.14200.149*
H28B0.58990.2266−0.16410.149*
H28C0.65310.1081−0.16850.149*
C290.7922 (3)−0.0014 (3)−0.0138 (3)0.0739 (10)
H29A0.7951−0.0081−0.07850.089*
H29B0.7731−0.07290.01430.089*
C300.9373 (3)0.0365 (2)0.0140 (3)0.0741 (10)
H30A0.93500.04070.07900.089*
H30B0.95410.1093−0.01210.089*
C310.1777 (3)0.0473 (2)0.42478 (16)0.0420 (6)
C320.2506 (3)−0.0499 (2)0.41235 (17)0.0493 (7)
H320.3417−0.06160.43580.059*
C330.1875 (3)−0.1296 (2)0.36497 (17)0.0490 (7)
H330.2373−0.19470.35630.059*
C340.0517 (3)−0.1139 (2)0.33031 (16)0.0449 (6)
C35−0.0224 (3)−0.0178 (2)0.34588 (18)0.0504 (7)
H35−0.1151−0.00690.32450.060*
C360.0403 (3)0.0617 (2)0.39292 (17)0.0507 (7)
H36−0.01070.12580.40330.061*
C370.2471 (3)0.1394 (2)0.46745 (18)0.0497 (7)
C38−0.0130 (3)−0.1938 (2)0.27258 (19)0.0518 (7)
N10.4693 (2)0.72048 (18)0.46235 (15)0.0498 (6)
N20.3174 (2)0.58270 (18)0.48811 (13)0.0442 (5)
N30.9751 (2)0.58143 (17)0.14404 (14)0.0445 (5)
N40.81999 (19)0.49945 (16)0.05991 (13)0.0393 (5)
N50.6745 (2)0.07253 (18)0.01097 (17)0.0530 (6)
N60.5129 (2)0.20832 (19)0.00184 (15)0.0567 (6)
O10.3721 (2)0.11390 (16)0.50186 (14)0.0674 (6)
H10.40490.16750.52440.081*
O20.1950 (2)0.22979 (17)0.46676 (16)0.0793 (7)
O30.0626 (2)−0.28314 (16)0.26517 (13)0.0667 (6)
H3A0.0214−0.32370.23250.080*
O4−0.1239 (2)−0.17682 (18)0.23391 (17)0.0881 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0354 (13)0.0509 (17)0.0473 (14)−0.0004 (12)−0.0090 (12)−0.0023 (12)
C20.0352 (13)0.0505 (17)0.0462 (14)−0.0008 (12)−0.0111 (12)−0.0054 (12)
C30.0593 (17)0.0555 (19)0.0567 (17)−0.0048 (14)−0.0188 (15)−0.0092 (14)
C40.086 (2)0.082 (3)0.0530 (18)0.008 (2)−0.0140 (18)−0.0234 (17)
C50.067 (2)0.101 (3)0.0458 (16)0.007 (2)0.0036 (15)−0.0110 (18)
C60.0447 (15)0.077 (2)0.0550 (17)−0.0084 (14)−0.0038 (14)0.0042 (16)
C70.0386 (14)0.0508 (18)0.0563 (16)0.0061 (13)−0.0086 (13)−0.0128 (13)
C80.073 (2)0.083 (3)0.073 (2)0.0173 (18)−0.0005 (18)−0.0272 (18)
C90.0306 (12)0.0401 (15)0.0448 (13)0.0012 (10)−0.0050 (11)−0.0063 (11)
C100.0303 (11)0.0393 (15)0.0413 (13)0.0020 (10)−0.0022 (11)−0.0058 (11)
C110.0502 (15)0.0467 (18)0.0603 (16)−0.0047 (13)−0.0004 (14)−0.0116 (13)
C120.074 (2)0.0376 (17)0.0702 (19)0.0023 (15)0.0017 (17)0.0047 (14)
C130.0659 (19)0.064 (2)0.0545 (17)0.0139 (16)−0.0068 (15)0.0121 (15)
C140.0465 (15)0.062 (2)0.0512 (15)0.0058 (14)−0.0139 (13)−0.0031 (14)
C150.0321 (12)0.0407 (15)0.0520 (14)−0.0006 (11)−0.0035 (12)−0.0019 (12)
C160.0524 (16)0.0495 (18)0.079 (2)0.0006 (13)−0.0095 (16)0.0099 (15)
C170.0347 (13)0.067 (2)0.0529 (15)−0.0090 (13)−0.0040 (12)0.0059 (13)
C180.0348 (13)0.0659 (19)0.0522 (15)−0.0069 (12)−0.0052 (12)0.0051 (13)
C190.0336 (13)0.0634 (19)0.0452 (14)−0.0010 (12)−0.0112 (12)−0.0094 (12)
C200.0348 (12)0.0491 (16)0.0399 (13)−0.0020 (11)−0.0075 (11)−0.0051 (11)
C210.0346 (13)0.0450 (17)0.0704 (19)−0.0064 (11)−0.0049 (14)−0.0025 (14)
C220.0335 (13)0.0458 (16)0.0601 (17)−0.0004 (11)−0.0031 (13)−0.0071 (13)
C230.0556 (18)0.074 (2)0.071 (2)0.0005 (16)0.0074 (17)−0.0108 (17)
C240.081 (3)0.118 (4)0.075 (3)−0.013 (2)0.014 (2)−0.008 (2)
C250.092 (3)0.117 (4)0.073 (2)−0.026 (3)−0.008 (2)0.029 (2)
C260.064 (2)0.060 (2)0.104 (3)−0.0069 (16)−0.018 (2)0.021 (2)
C270.0495 (16)0.0558 (19)0.0654 (18)−0.0039 (14)0.0031 (15)−0.0061 (15)
C280.099 (3)0.130 (4)0.068 (2)−0.011 (3)0.016 (2)−0.008 (2)
C290.0360 (14)0.053 (2)0.135 (3)0.0018 (13)0.0092 (17)−0.0380 (19)
C300.0364 (14)0.053 (2)0.135 (3)−0.0005 (13)0.0082 (17)−0.0372 (19)
C310.0445 (14)0.0370 (15)0.0443 (14)−0.0032 (11)−0.0018 (12)0.0001 (11)
C320.0450 (14)0.0439 (17)0.0599 (16)0.0015 (12)−0.0139 (13)−0.0032 (13)
C330.0487 (15)0.0383 (16)0.0607 (16)0.0024 (12)−0.0113 (14)−0.0041 (12)
C340.0452 (14)0.0405 (15)0.0488 (14)−0.0043 (12)−0.0051 (12)0.0039 (12)
C350.0419 (14)0.0489 (18)0.0606 (16)−0.0020 (12)−0.0092 (13)0.0005 (13)
C360.0465 (15)0.0448 (17)0.0608 (16)0.0066 (12)−0.0019 (14)−0.0033 (13)
C370.0494 (15)0.0449 (18)0.0549 (16)−0.0024 (13)−0.0004 (14)−0.0028 (13)
C380.0482 (15)0.0445 (17)0.0636 (17)−0.0044 (13)−0.0095 (14)−0.0044 (13)
N10.0382 (12)0.0499 (14)0.0623 (14)−0.0034 (10)−0.0078 (11)−0.0085 (11)
N20.0304 (10)0.0540 (14)0.0484 (12)−0.0042 (10)−0.0031 (10)−0.0044 (10)
N30.0361 (11)0.0408 (13)0.0579 (13)−0.0021 (9)−0.0122 (10)−0.0067 (10)
N40.0298 (10)0.0412 (13)0.0478 (11)−0.0028 (9)−0.0090 (9)−0.0061 (9)
N50.0352 (11)0.0444 (14)0.0801 (16)−0.0001 (10)0.0049 (12)−0.0153 (12)
N60.0486 (13)0.0566 (16)0.0644 (15)0.0090 (11)−0.0013 (12)−0.0023 (12)
O10.0630 (12)0.0492 (13)0.0933 (15)−0.0026 (10)−0.0258 (12)−0.0187 (10)
O20.0744 (14)0.0431 (13)0.1239 (19)0.0057 (11)−0.0263 (13)−0.0218 (12)
O30.0662 (12)0.0494 (13)0.0883 (14)0.0003 (10)−0.0303 (11)−0.0199 (11)
O40.0714 (14)0.0772 (17)0.1216 (19)0.0137 (12)−0.0481 (15)−0.0336 (14)
Geometric parameters (Å, °) top
C1—N11.388 (3)C20—C20ii1.506 (4)
C1—C21.388 (4)C20—H20A0.9700
C1—C61.393 (4)C20—H20B0.9700
C2—N21.378 (3)C21—N51.377 (3)
C2—C31.384 (4)C21—C261.387 (4)
C3—C41.367 (4)C21—C221.392 (3)
C3—H30.9300C22—C231.377 (4)
C4—C51.377 (5)C22—N61.387 (3)
C4—H40.9300C23—C241.353 (5)
C5—C61.367 (4)C23—H230.9300
C5—H50.9300C24—C251.381 (5)
C6—H60.9300C24—H240.9300
C7—N11.319 (3)C25—C261.380 (5)
C7—N21.355 (3)C25—H250.9300
C7—C81.482 (4)C26—H260.9300
C8—H8A0.9600C27—N61.308 (3)
C8—H8B0.9600C27—N51.363 (3)
C8—H8C0.9600C27—C281.479 (4)
C9—N31.382 (3)C28—H28A0.9600
C9—C141.384 (3)C28—H28B0.9600
C9—C101.391 (3)C28—H28C0.9600
C10—C111.375 (4)C29—N51.456 (3)
C10—N41.390 (3)C29—C301.502 (4)
C11—C121.371 (4)C29—H29A0.9700
C11—H110.9300C29—H29B0.9700
C12—C131.393 (4)C30—C30iii1.515 (5)
C12—H120.9300C30—H30A0.9700
C13—C141.359 (4)C30—H30B0.9700
C13—H130.9300C31—C361.377 (3)
C14—H140.9300C31—C321.381 (3)
C15—N31.318 (3)C31—C371.488 (4)
C15—N41.353 (3)C32—C331.382 (4)
C15—C161.477 (4)C32—H320.9300
C16—H16A0.9600C33—C341.382 (3)
C16—H16B0.9600C33—H330.9300
C16—H16C0.9600C34—C351.383 (4)
C17—N21.462 (3)C34—C381.482 (4)
C17—C181.510 (3)C35—C361.376 (4)
C17—H17A0.9700C35—H350.9300
C17—H17B0.9700C36—H360.9300
C18—C18i1.511 (5)C37—O21.206 (3)
C18—H18A0.9700C37—O11.308 (3)
C18—H18B0.9700C38—O41.205 (3)
C19—N41.463 (3)C38—O31.301 (3)
C19—C201.507 (3)O1—H10.8199
C19—H19A0.9700O3—H3A0.8197
C19—H19B0.9700
N1—C1—C2109.2 (2)N5—C21—C26133.3 (3)
N1—C1—C6130.6 (3)N5—C21—C22105.5 (2)
C2—C1—C6120.2 (3)C26—C21—C22121.2 (3)
N2—C2—C3132.0 (3)C23—C22—N6129.6 (2)
N2—C2—C1105.9 (2)C23—C22—C21120.7 (3)
C3—C2—C1122.1 (3)N6—C22—C21109.7 (2)
C4—C3—C2116.5 (3)C24—C23—C22118.1 (3)
C4—C3—H3121.8C24—C23—H23121.0
C2—C3—H3121.8C22—C23—H23121.0
C3—C4—C5122.1 (3)C23—C24—C25122.0 (4)
C3—C4—H4118.9C23—C24—H24119.0
C5—C4—H4118.9C25—C24—H24119.0
C6—C5—C4121.8 (3)C26—C25—C24121.1 (3)
C6—C5—H5119.1C26—C25—H25119.4
C4—C5—H5119.1C24—C25—H25119.4
C5—C6—C1117.2 (3)C25—C26—C21117.0 (3)
C5—C6—H6121.4C25—C26—H26121.5
C1—C6—H6121.4C21—C26—H26121.5
N1—C7—N2112.3 (2)N6—C27—N5113.0 (3)
N1—C7—C8124.5 (3)N6—C27—C28124.1 (3)
N2—C7—C8123.2 (3)N5—C27—C28122.9 (3)
C7—C8—H8A109.5C27—C28—H28A109.5
C7—C8—H8B109.5C27—C28—H28B109.5
H8A—C8—H8B109.5H28A—C28—H28B109.5
C7—C8—H8C109.5C27—C28—H28C109.5
H8A—C8—H8C109.5H28A—C28—H28C109.5
H8B—C8—H8C109.5H28B—C28—H28C109.5
N3—C9—C14130.0 (2)N5—C29—C30112.6 (2)
N3—C9—C10109.79 (19)N5—C29—H29A109.1
C14—C9—C10120.2 (2)C30—C29—H29A109.1
C11—C10—N4132.6 (2)N5—C29—H29B109.1
C11—C10—C9122.3 (2)C30—C29—H29B109.1
N4—C10—C9105.0 (2)H29A—C29—H29B107.8
C12—C11—C10116.4 (2)C29—C30—C30iii113.8 (3)
C12—C11—H11121.8C29—C30—H30A108.8
C10—C11—H11121.8C30iii—C30—H30A108.8
C11—C12—C13121.8 (3)C29—C30—H30B108.8
C11—C12—H12119.1C30iii—C30—H30B108.8
C13—C12—H12119.1H30A—C30—H30B107.7
C14—C13—C12121.4 (2)C36—C31—C32119.4 (2)
C14—C13—H13119.3C36—C31—C37119.0 (2)
C12—C13—H13119.3C32—C31—C37121.6 (2)
C13—C14—C9117.8 (2)C31—C32—C33119.8 (2)
C13—C14—H14121.1C31—C32—H32120.1
C9—C14—H14121.1C33—C32—H32120.1
N3—C15—N4112.5 (2)C34—C33—C32120.9 (2)
N3—C15—C16124.6 (2)C34—C33—H33119.6
N4—C15—C16122.9 (2)C32—C33—H33119.6
C15—C16—H16A109.5C33—C34—C35118.8 (2)
C15—C16—H16B109.5C33—C34—C38122.0 (2)
H16A—C16—H16B109.5C35—C34—C38119.1 (2)
C15—C16—H16C109.5C36—C35—C34120.3 (2)
H16A—C16—H16C109.5C36—C35—H35119.8
H16B—C16—H16C109.5C34—C35—H35119.8
N2—C17—C18112.0 (2)C35—C36—C31120.7 (2)
N2—C17—H17A109.2C35—C36—H36119.6
C18—C17—H17A109.2C31—C36—H36119.6
N2—C17—H17B109.2O2—C37—O1123.6 (3)
C18—C17—H17B109.2O2—C37—C31122.7 (2)
H17A—C17—H17B107.9O1—C37—C31113.7 (2)
C17—C18—C18i110.9 (3)O4—C38—O3122.7 (3)
C17—C18—H18A109.5O4—C38—C34123.2 (3)
C18i—C18—H18A109.5O3—C38—C34114.1 (2)
C17—C18—H18B109.5C7—N1—C1105.6 (2)
C18i—C18—H18B109.5C7—N2—C2107.1 (2)
H18A—C18—H18B108.0C7—N2—C17128.4 (2)
N4—C19—C20112.81 (19)C2—N2—C17124.5 (2)
N4—C19—H19A109.0C15—N3—C9105.54 (19)
C20—C19—H19A109.0C15—N4—C10107.14 (18)
N4—C19—H19B109.0C15—N4—C19126.2 (2)
C20—C19—H19B109.0C10—N4—C19126.5 (2)
H19A—C19—H19B107.8C27—N5—C21106.6 (2)
C20ii—C20—C19111.6 (2)C27—N5—C29127.9 (3)
C20ii—C20—H20A109.3C21—N5—C29125.4 (3)
C19—C20—H20A109.3C27—N6—C22105.1 (2)
C20ii—C20—H20B109.3C37—O1—H1109.3
C19—C20—H20B109.3C38—O3—H3A109.4
H20A—C20—H20B108.0
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1iv0.821.832.609 (3)157
O3—H3A···N3v0.821.872.668 (3)165
Symmetry codes: (iv) −x+1, −y+1, −z+1; (v) x−1, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.821.832.609 (3)157
O3—H3A···N3ii0.821.872.668 (3)165
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y−1, z.
Acknowledgements top

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

references
References top

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.