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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o838.
Published online 2008 April 16. doi:  10.1107/S1600536808009665
PMCID: PMC2961189

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

Abstract

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 [triangle]); Ma et al. (2000 [triangle]).

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Object name is e-64-0o838-scheme1.jpg

Experimental

Crystal data

  • 2C8H6O4·3C20H22N4
  • M r = 1286.88
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o838-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.071
  • wR(F 2) = 0.163
  • S = 1.01
  • 7573 reflections
  • 437 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.21 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

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.

Crystal data

2C8H6O4·3C20H22N4Z = 1
Mr = 1286.88F000 = 682
Triclinic, P1Dx = 1.268 Mg m3
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 mm1
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

Rigaku R-AXIS RAPID diffractometer7573 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

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 Å3
7573 reflectionsΔρmin = −0.21 e Å3
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

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2066).

References

  • Dale, S. H. & Elsegood, M. R. J. (2004). Acta Cryst. C60, o444–o448. [PubMed]
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Ma, J.-F., Liu, J.-F., Liu, Y.-C., Xing, Y., Jia, H.-Q. & Lin, Y.-H. (2000). New J. Chem.24, 759–763.
  • Rigaku (1998). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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