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The structure of the title compound, C32H22N6, comprises two unique mol­ecules that associate via N—H...N interactions to form a single convoluted hydrogen-bonded polymer chain. The dihedral angles between the indole rings and the substituted pyridyl rings are 13.43 (14) and 22.34 (12) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800019620/ob6017sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800019620/ob6017Isup2.hkl
Contains datablock I

CCDC reference: 155888

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.109
  • Data-to-parameter ratio = 11.8

checkCIF results

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ADDSYM reports no extra symmetry




Comment top

NO COMMENT

Experimental top

The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) were grown from an ethanol solution.

Refinement top

All H atoms were included in the refinement at calculated positions as riding models, with C—H set to 0.95 Å, except for the indole NH group, which was located on difference syntheses and for which both positional and displacement parameters were refined. The unit cell for (I) was initially determined as orthorhombic C [a = 21.5564 (8), b = 32.161 (1), c = 6.8627 (4) Å], but it was not possible to obtain a solution in this setting. The structure was eventually solved as primitive monoclinic in P21/n. However, the refinement was poor, R1 was around 26% and the ellipsoids were unreasonable. It was noted that a and c were approximately equal in length and the structure was refined as a pseudo-merohedral twin (twin law: 001, 010, 100). This resulted in a final R1 value of 4.4%, sensible ellipsoids and a twin component of 0.46 (1).

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The mlecular configuration and atom-numbering scheme for (I), showing 30% probability ellipsoids.
2-(4-Pyridyl)pyrrolo[3,2-h]quinoline top
Crystal data top
C32H22N6Dx = 1.370 Mg m3
Mr = 490.56Melting point: 484-487 K K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 19.3539 (8) ÅCell parameters from 8137 reflections
b = 6.8609 (3) Åθ = 2.9–30.5°
c = 19.3579 (8) ŵ = 0.08 mm1
β = 112.325 (2)°T = 150 K
V = 2377.77 (17) Å3Prism, colourless
Z = 40.28 × 0.12 × 0.04 mm
F(000) = 1024
Data collection top
Enraf Nonius KappaCCD area detector
diffractometer
4179 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode3199 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
Detector resolution: 9.091 pixels mm-1θmax = 25.0°, θmin = 3.0°
ϕ and ω scansh = 2222
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 88
Tmin = 0.977, Tmax = 0.997l = 2321
11617 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0672P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max = 0.001
4179 reflectionsΔρmax = 0.22 e Å3
353 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0087 (13)
Crystal data top
C32H22N6V = 2377.77 (17) Å3
Mr = 490.56Z = 4
Monoclinic, P21/nMo Kα radiation
a = 19.3539 (8) ŵ = 0.08 mm1
b = 6.8609 (3) ÅT = 150 K
c = 19.3579 (8) Å0.28 × 0.12 × 0.04 mm
β = 112.325 (2)°
Data collection top
Enraf Nonius KappaCCD area detector
diffractometer
4179 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
3199 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.997Rint = 0.062
11617 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 0.89Δρmax = 0.22 e Å3
4179 reflectionsΔρmin = 0.21 e Å3
353 parameters
Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 1.4708 (0.0272) x - 6.6299 (0.0025) y + 4.9610 (0.0258) z = 3.5277 (0.0290)

* 0.0035 (0.0016) N1A * 0.0001 (0.0017) C2A * -0.0035 (0.0017) C3A * 0.0055 (0.0016) C4A * -0.0056 (0.0016) C13A

Rms deviation of fitted atoms = 0.0041

- 1.7517 (0.0186) x - 5.4799 (0.0046) y + 11.3177 (0.0171) z = 11.1609 (0.0200)

Angle to previous plane (with approximate e.s.d.) = 22.34 (0.12)

* -0.0027 (0.0018) N14A * 0.0092 (0.0018) C15A * -0.0064 (0.0018) C16A * -0.0023 (0.0018) C17A * 0.0085 (0.0019) C18A * -0.0063 (0.0019) C19A

Rms deviation of fitted atoms = 0.0064

7.2754 (0.0241) x + 6.3302 (0.0036) y - 1.2228 (0.0263) z = 1.1150 (0.0161)

Angle to previous plane (with approximate e.s.d.) = 43.97 (0.09)

* 0.0083 (0.0015) N1B * -0.0061 (0.0016) C2B * 0.0017 (0.0016) C3B * 0.0033 (0.0015) C4B * -0.0072 (0.0016) C13B

Rms deviation of fitted atoms = 0.0058

11.0024 (0.0188) x + 5.5454 (0.0049) y - 1.4334 (0.0198) z = 1.4377 (0.0162)

Angle to previous plane (with approximate e.s.d.) = 13.43 (0.14)

* -0.0007 (0.0018) N14B * 0.0056 (0.0020) C15B * -0.0041 (0.0020) C16B * -0.0018 (0.0018) C17B * 0.0065 (0.0019) C18B * -0.0054 (0.0020) C19B

Rms deviation of fitted atoms = 0.0045

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.15848 (12)0.2457 (4)1.08718 (12)0.0274 (5)
H1A0.1606 (16)0.211 (5)1.0421 (17)0.046 (9)*
C2A0.21773 (15)0.2826 (4)1.15331 (14)0.0296 (6)
C3A0.18996 (15)0.3292 (4)1.20662 (15)0.0326 (7)
H3A0.21850.36181.25720.039*
C4A0.11103 (15)0.3200 (4)1.17275 (14)0.0307 (7)
C5A0.05249 (16)0.3459 (4)1.19924 (16)0.0368 (7)
H5A0.06370.37851.25000.044*
C6A0.01954 (17)0.3237 (4)1.15132 (17)0.0395 (7)
H6A0.05840.33371.16980.047*
C7A0.03836 (16)0.2855 (4)1.07322 (16)0.0328 (7)
C8A0.11228 (16)0.2788 (4)1.02123 (17)0.0391 (8)
H8A0.15270.29361.03720.047*
C9A0.12561 (16)0.2508 (5)0.94751 (18)0.0422 (8)
H9A0.17530.24700.91140.051*
C10A0.06551 (16)0.2281 (4)0.92620 (17)0.0385 (7)
H10A0.07600.20900.87460.046*
N11A0.00560 (13)0.2309 (3)0.97225 (12)0.0329 (6)
C12A0.01843 (15)0.2601 (4)1.04585 (15)0.0295 (7)
C13A0.09330 (15)0.2696 (4)1.09789 (14)0.0273 (6)
N14A0.44505 (12)0.2436 (4)1.17273 (12)0.0325 (6)
C15A0.42470 (15)0.3467 (4)1.22055 (14)0.0333 (7)
H15A0.46270.41251.26010.040*
C16A0.35186 (14)0.3638 (4)1.21620 (14)0.0317 (6)
H16A0.34070.44201.25110.038*
C17A0.29513 (14)0.2652 (4)1.16004 (13)0.0268 (6)
C18A0.31586 (14)0.1556 (4)1.11112 (14)0.0290 (6)
H18A0.27930.08401.07230.035*
C19A0.38967 (14)0.1501 (4)1.11860 (14)0.0319 (7)
H19A0.40200.07601.08340.038*
N1B0.08954 (13)0.2008 (3)0.65358 (12)0.0275 (5)
H1B0.0473 (18)0.231 (5)0.6572 (17)0.054 (10)*
C2B0.15420 (14)0.1351 (4)0.71018 (14)0.0266 (6)
C3B0.20314 (14)0.0741 (4)0.67907 (14)0.0304 (6)
H3B0.25180.02380.70540.037*
C4B0.16844 (14)0.0991 (4)0.60068 (14)0.0293 (6)
C5B0.18996 (16)0.0619 (4)0.53947 (15)0.0339 (7)
H5B0.23800.01020.54770.041*
C6B0.14134 (16)0.1008 (4)0.46924 (16)0.0376 (7)
H6B0.15610.07670.42850.045*
C7B0.06835 (16)0.1771 (4)0.45472 (15)0.0319 (7)
C8B0.01579 (18)0.2151 (4)0.38216 (16)0.0389 (8)
H8B0.02850.19330.34000.047*
C9B0.05314 (17)0.2831 (4)0.37279 (16)0.0384 (8)
H9B0.08890.31000.32420.046*
C10B0.07059 (16)0.3125 (4)0.43517 (15)0.0359 (7)
H10B0.11940.35800.42740.043*
N11B0.02409 (12)0.2817 (3)0.50478 (11)0.0301 (6)
C12B0.04491 (15)0.2142 (4)0.51387 (15)0.0283 (6)
C13B0.09753 (15)0.1763 (4)0.58688 (14)0.0273 (6)
N14B0.17849 (12)0.1479 (3)0.93954 (12)0.0334 (6)
C15B0.22530 (15)0.0499 (4)0.91572 (14)0.0353 (7)
H15B0.26550.01820.95200.042*
C16B0.21956 (15)0.0408 (4)0.84310 (14)0.0341 (6)
H16B0.25440.03320.83030.041*
C17B0.16212 (14)0.1410 (4)0.78820 (14)0.0277 (6)
C18B0.11361 (16)0.2448 (4)0.81175 (14)0.0309 (7)
H18B0.07390.31710.77670.037*
C19B0.12297 (14)0.2434 (4)0.88622 (14)0.0313 (7)
H19B0.08820.31380.90050.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0270 (14)0.0283 (13)0.0270 (13)0.0002 (10)0.0106 (10)0.0021 (10)
C2A0.0329 (16)0.0288 (16)0.0244 (14)0.0009 (12)0.0078 (12)0.0031 (11)
C3A0.0380 (16)0.0334 (17)0.0259 (14)0.0034 (13)0.0116 (12)0.0010 (12)
C4A0.0398 (17)0.0237 (16)0.0331 (15)0.0026 (12)0.0189 (13)0.0034 (12)
C5A0.0466 (17)0.0343 (17)0.0368 (16)0.0054 (14)0.0241 (14)0.0044 (13)
C6A0.0438 (18)0.0364 (18)0.0502 (18)0.0082 (14)0.0313 (15)0.0037 (15)
C7A0.0362 (16)0.0236 (15)0.0452 (17)0.0015 (12)0.0229 (14)0.0035 (13)
C8A0.0340 (18)0.0303 (17)0.059 (2)0.0013 (12)0.0238 (16)0.0022 (14)
C9A0.0269 (18)0.0366 (18)0.058 (2)0.0002 (13)0.0102 (15)0.0006 (16)
C10A0.0390 (19)0.0321 (17)0.0396 (16)0.0009 (14)0.0097 (14)0.0001 (14)
N11A0.0347 (14)0.0298 (14)0.0321 (13)0.0023 (11)0.0101 (11)0.0007 (11)
C12A0.0326 (17)0.0215 (14)0.0362 (16)0.0004 (12)0.0151 (13)0.0007 (12)
C13A0.0311 (16)0.0234 (15)0.0294 (15)0.0017 (12)0.0138 (12)0.0035 (12)
N14A0.0324 (14)0.0340 (14)0.0280 (12)0.0000 (11)0.0080 (10)0.0037 (11)
C15A0.0342 (15)0.0339 (17)0.0271 (14)0.0020 (12)0.0063 (12)0.0006 (12)
C16A0.0344 (15)0.0334 (16)0.0238 (13)0.0027 (13)0.0073 (11)0.0013 (12)
C17A0.0284 (16)0.0279 (15)0.0210 (13)0.0048 (11)0.0060 (12)0.0053 (11)
C18A0.0288 (15)0.0327 (16)0.0229 (13)0.0006 (12)0.0069 (11)0.0002 (12)
C19A0.0328 (16)0.0318 (17)0.0277 (14)0.0020 (13)0.0078 (12)0.0021 (12)
N1B0.0265 (14)0.0289 (13)0.0274 (13)0.0002 (10)0.0104 (11)0.0030 (10)
C2B0.0275 (14)0.0256 (14)0.0266 (13)0.0026 (12)0.0102 (11)0.0011 (12)
C3B0.0280 (14)0.0259 (15)0.0340 (14)0.0016 (11)0.0078 (12)0.0029 (12)
C4B0.0310 (14)0.0233 (15)0.0353 (15)0.0044 (11)0.0145 (11)0.0051 (12)
C5B0.0374 (15)0.0284 (16)0.0408 (16)0.0031 (13)0.0205 (13)0.0059 (13)
C6B0.0527 (18)0.0301 (16)0.0396 (16)0.0096 (15)0.0283 (15)0.0109 (14)
C7B0.0449 (18)0.0229 (15)0.0324 (15)0.0088 (13)0.0196 (13)0.0047 (12)
C8B0.058 (2)0.0286 (17)0.0328 (16)0.0145 (15)0.0209 (15)0.0050 (13)
C9B0.052 (2)0.0271 (16)0.0300 (16)0.0106 (14)0.0086 (14)0.0018 (12)
C10B0.0393 (17)0.0293 (17)0.0333 (16)0.0069 (12)0.0072 (13)0.0019 (12)
N11B0.0361 (14)0.0235 (13)0.0282 (12)0.0043 (10)0.0094 (10)0.0004 (9)
C12B0.0372 (16)0.0167 (14)0.0327 (15)0.0053 (11)0.0150 (12)0.0004 (11)
C13B0.0334 (15)0.0237 (15)0.0288 (14)0.0050 (12)0.0163 (12)0.0039 (11)
N14B0.0330 (13)0.0363 (14)0.0276 (12)0.0008 (11)0.0078 (11)0.0007 (11)
C15B0.0344 (15)0.0349 (17)0.0314 (15)0.0064 (13)0.0068 (12)0.0035 (13)
C16B0.0371 (15)0.0313 (16)0.0325 (15)0.0063 (13)0.0118 (12)0.0003 (13)
C17B0.0270 (14)0.0236 (15)0.0305 (14)0.0046 (12)0.0088 (12)0.0013 (12)
C18B0.0285 (15)0.0322 (16)0.0276 (14)0.0028 (12)0.0057 (12)0.0012 (12)
C19B0.0261 (15)0.0345 (16)0.0316 (15)0.0023 (12)0.0090 (13)0.0027 (13)
Geometric parameters (Å, º) top
N1A—C2A1.379 (3)N1B—C13B1.368 (3)
N1A—C13A1.364 (3)N1B—C2B1.388 (3)
N1A—H1A0.92 (3)N1B—H1B0.87 (3)
C2A—C3A1.370 (4)C2B—C3B1.367 (4)
C2A—C17A1.458 (4)C2B—C17B1.459 (4)
C3A—C4A1.417 (4)C3B—C4B1.417 (4)
C3A—H3A0.95C3B—H3B0.95
C4A—C13A1.400 (4)C4B—C13B1.399 (4)
C4A—C5A1.421 (3)C4B—C5B1.420 (3)
C5A—C6A1.358 (4)C5B—C6B1.354 (4)
C5A—H5A0.95C5B—H5B0.95
C6A—C7A1.438 (4)C6B—C7B1.431 (4)
C6A—H6A0.95C6B—H6B0.95
C7A—C12A1.401 (4)C7B—C12B1.406 (4)
C7A—C8A1.403 (4)C7B—C8B1.411 (4)
C8A—C9A1.364 (4)C8B—C9B1.359 (4)
C8A—H8A0.95C8B—H8B0.95
C9A—C10A1.382 (4)C9B—C10B1.387 (4)
C9A—H9A0.95C9B—H9B0.95
C10A—N11A1.326 (3)C10B—N11B1.323 (3)
C10A—H10A0.95C10B—H10B0.95
N11A—C12A1.365 (3)N11B—C12B1.360 (4)
C12A—C13A1.418 (4)C12B—C13B1.417 (4)
N14A—C15A1.338 (4)N14B—C19B1.344 (3)
N14A—C19A1.343 (3)N14B—C15B1.343 (3)
C15A—C16A1.385 (4)C15B—C16B1.369 (4)
C15A—H15A0.95C15B—H15B0.95
C16A—C17A1.392 (4)C16B—C17B1.393 (4)
C16A—H16A0.95C16B—H16B0.95
C17A—C18A1.383 (4)C17B—C18B1.386 (4)
C18A—C19A1.381 (4)C18B—C19B1.383 (4)
C18A—H18A0.95C18B—H18B0.95
C19A—H19A0.95C19B—H19B0.95
C2A—N1A—C13A109.1 (2)C13B—N1B—C2B108.3 (2)
C2A—N1A—H1A127.4 (18)C13B—N1B—H1B123 (2)
C13A—N1A—H1A123.5 (18)C2B—N1B—H1B127 (2)
C3A—C2A—N1A108.4 (2)C3B—C2B—N1B108.6 (2)
C3A—C2A—C17A129.4 (2)C3B—C2B—C17B130.3 (2)
N1A—C2A—C17A122.1 (2)N1B—C2B—C17B121.1 (2)
C2A—C3A—C4A107.7 (2)C2B—C3B—C4B108.0 (2)
C2A—C3A—H3A126.2C2B—C3B—H3B126.0
C4A—C3A—H3A126.2C4B—C3B—H3B126.0
C13A—C4A—C3A106.7 (2)C13B—C4B—C5B119.1 (2)
C13A—C4A—C5A119.3 (3)C13B—C4B—C3B106.4 (2)
C3A—C4A—C5A134.0 (3)C5B—C4B—C3B134.6 (2)
C6A—C5A—C4A119.5 (3)C6B—C5B—C4B119.3 (3)
C6A—C5A—H5A120.3C6B—C5B—H5B120.3
C4A—C5A—H5A120.3C4B—C5B—H5B120.3
C5A—C6A—C7A121.5 (3)C5B—C6B—C7B121.8 (3)
C5A—C6A—H6A119.2C5B—C6B—H6B119.1
C7A—C6A—H6A119.2C7B—C6B—H6B119.1
C12A—C7A—C8A117.2 (3)C12B—C7B—C8B116.3 (3)
C12A—C7A—C6A119.9 (3)C12B—C7B—C6B120.4 (2)
C8A—C7A—C6A122.8 (3)C8B—C7B—C6B123.2 (3)
C9A—C8A—C7A119.4 (3)C9B—C8B—C7B119.8 (3)
C9A—C8A—H8A120.3C9B—C8B—H8B120.1
C7A—C8A—H8A120.3C7B—C8B—H8B120.1
C8A—C9A—C10A118.8 (3)C8B—C9B—C10B119.0 (3)
C8A—C9A—H9A120.6C8B—C9B—H9B120.5
C10A—C9A—H9A120.6C10B—C9B—H9B120.5
N11A—C10A—C9A125.0 (3)N11B—C10B—C9B124.6 (3)
N11A—C10A—H10A117.5N11B—C10B—H10B117.7
C9A—C10A—H10A117.5C9B—C10B—H10B117.7
C10A—N11A—C12A115.8 (3)C10B—N11B—C12B116.2 (2)
N11A—C12A—C7A123.7 (3)N11B—C12B—C7B124.1 (2)
N11A—C12A—C13A118.7 (2)N11B—C12B—C13B119.3 (2)
C7A—C12A—C13A117.5 (2)C7B—C12B—C13B116.5 (3)
N1A—C13A—C4A108.1 (2)N1B—C13B—C4B108.7 (2)
N1A—C13A—C12A129.9 (2)N1B—C13B—C12B128.5 (2)
C4A—C13A—C12A122.0 (2)C4B—C13B—C12B122.8 (2)
C15A—N14A—C19A115.8 (2)C19B—N14B—C15B115.3 (2)
N14A—C15A—C16A124.3 (2)N14B—C15B—C16B125.0 (3)
N14A—C15A—H15A117.9N14B—C15B—H15B117.5
C16A—C15A—H15A117.9C16B—C15B—H15B117.5
C15A—C16A—C17A119.3 (3)C15B—C16B—C17B119.4 (3)
C15A—C16A—H16A120.4C15B—C16B—H16B120.3
C17A—C16A—H16A120.4C17B—C16B—H16B120.3
C18A—C17A—C16A116.8 (2)C18B—C17B—C16B116.5 (2)
C18A—C17A—C2A122.6 (2)C18B—C17B—C2B122.4 (2)
C16A—C17A—C2A120.6 (2)C16B—C17B—C2B121.0 (2)
C19A—C18A—C17A120.0 (2)C19B—C18B—C17B120.1 (3)
C19A—C18A—H18A120.0C19B—C18B—H18B119.9
C17A—C18A—H18A120.0C17B—C18B—H18B119.9
N14A—C19A—C18A123.8 (3)N14B—C19B—C18B123.6 (3)
N14A—C19A—H19A118.1N14B—C19B—H19B118.2
C18A—C19A—H19A118.1C18B—C19B—H19B118.2
C13A—N1A—C2A—C3A0.3 (3)C13B—N1B—C2B—C3B1.4 (3)
C13A—N1A—C2A—C17A178.8 (2)C13B—N1B—C2B—C17B179.5 (2)
N1A—C2A—C3A—C4A0.3 (3)N1B—C2B—C3B—C4B0.8 (3)
C17A—C2A—C3A—C4A177.9 (3)C17B—C2B—C3B—C4B179.8 (3)
C2A—C3A—C4A—C13A0.9 (3)C2B—C3B—C4B—C13B0.1 (3)
C2A—C3A—C4A—C5A177.5 (3)C2B—C3B—C4B—C5B179.4 (3)
C13A—C4A—C5A—C6A0.8 (4)C13B—C4B—C5B—C6B0.4 (4)
C3A—C4A—C5A—C6A179.0 (3)C3B—C4B—C5B—C6B178.8 (3)
C4A—C5A—C6A—C7A3.6 (4)C4B—C5B—C6B—C7B0.5 (4)
C5A—C6A—C7A—C12A3.4 (4)C5B—C6B—C7B—C12B0.0 (4)
C5A—C6A—C7A—C8A174.3 (3)C5B—C6B—C7B—C8B178.5 (3)
C12A—C7A—C8A—C9A0.8 (4)C12B—C7B—C8B—C9B0.2 (4)
C6A—C7A—C8A—C9A176.9 (3)C6B—C7B—C8B—C9B178.3 (3)
C7A—C8A—C9A—C10A0.6 (4)C7B—C8B—C9B—C10B0.4 (4)
C8A—C9A—C10A—N11A0.1 (5)C8B—C9B—C10B—N11B1.0 (4)
C9A—C10A—N11A—C12A0.5 (4)C9B—C10B—N11B—C12B0.8 (4)
C10A—N11A—C12A—C7A0.2 (4)C10B—N11B—C12B—C7B0.1 (4)
C10A—N11A—C12A—C13A178.5 (2)C10B—N11B—C12B—C13B179.5 (2)
C8A—C7A—C12A—N11A0.5 (4)C8B—C7B—C12B—N11B0.4 (4)
C6A—C7A—C12A—N11A177.4 (3)C6B—C7B—C12B—N11B178.2 (2)
C8A—C7A—C12A—C13A179.1 (2)C8B—C7B—C12B—C13B180.0 (2)
C6A—C7A—C12A—C13A1.3 (4)C6B—C7B—C12B—C13B1.4 (4)
C2A—N1A—C13A—C4A0.9 (3)C2B—N1B—C13B—C4B1.5 (3)
C2A—N1A—C13A—C12A175.5 (3)C2B—N1B—C13B—C12B176.9 (3)
C3A—C4A—C13A—N1A1.1 (3)C5B—C4B—C13B—N1B179.6 (2)
C5A—C4A—C13A—N1A177.6 (2)C3B—C4B—C13B—N1B1.0 (3)
C3A—C4A—C13A—C12A175.7 (3)C5B—C4B—C13B—C12B1.9 (4)
C5A—C4A—C13A—C12A5.6 (4)C3B—C4B—C13B—C12B177.5 (2)
N11A—C12A—C13A—N1A3.1 (5)N11B—C12B—C13B—N1B1.0 (4)
C7A—C12A—C13A—N1A178.2 (3)C7B—C12B—C13B—N1B179.4 (2)
N11A—C12A—C13A—C4A172.9 (3)N11B—C12B—C13B—C4B177.3 (2)
C7A—C12A—C13A—C4A5.8 (4)C7B—C12B—C13B—C4B2.3 (4)
C19A—N14A—C15A—C16A1.2 (4)C19B—N14B—C15B—C16B0.6 (4)
N14A—C15A—C16A—C17A1.6 (4)N14B—C15B—C16B—C17B0.9 (5)
C15A—C16A—C17A—C18A0.4 (4)C15B—C16B—C17B—C18B0.2 (4)
C15A—C16A—C17A—C2A179.1 (2)C15B—C16B—C17B—C2B179.9 (2)
C3A—C2A—C17A—C18A157.1 (3)C3B—C2B—C17B—C18B166.0 (3)
N1A—C2A—C17A—C18A21.0 (4)N1B—C2B—C17B—C18B13.0 (4)
C3A—C2A—C17A—C16A24.3 (4)C3B—C2B—C17B—C16B14.1 (4)
N1A—C2A—C17A—C16A157.6 (3)N1B—C2B—C17B—C16B167.0 (2)
C16A—C17A—C18A—C19A1.0 (4)C16B—C17B—C18B—C19B0.8 (4)
C2A—C17A—C18A—C19A177.7 (2)C2B—C17B—C18B—C19B179.1 (3)
C15A—N14A—C19A—C18A0.3 (4)C15B—N14B—C19B—C18B0.5 (4)
C17A—C18A—C19A—N14A1.5 (4)C17B—C18B—C19B—N14B1.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N14B0.92 (3)2.18 (3)3.100 (3)173 (3)
N1B—H1B···N14Ai0.87 (3)2.12 (3)2.982 (3)171 (3)
C18A—H18A···N14B0.952.613.376 (3)138
C18B—H18B···N14Ai0.952.573.350 (3)139
C19B—H19B···N11A0.952.553.289 (4)135
Symmetry code: (i) x1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC32H22N6
Mr490.56
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)19.3539 (8), 6.8609 (3), 19.3579 (8)
β (°) 112.325 (2)
V3)2377.77 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.28 × 0.12 × 0.04
Data collection
DiffractometerEnraf Nonius KappaCCD area detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.977, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
11617, 4179, 3199
Rint0.062
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.109, 0.89
No. of reflections4179
No. of parameters353
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.21

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N14B0.92 (3)2.18 (3)3.100 (3)173 (3)
N1B—H1B···N14Ai0.87 (3)2.12 (3)2.982 (3)171 (3)
C18A—H18A···N14B0.952.613.376 (3)138.3
C18B—H18B···N14Ai0.952.573.350 (3)139.0
C19B—H19B···N11A0.952.553.289 (4)134.8
Symmetry code: (i) x1/2, y+1/2, z1/2.
 

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