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The title compound, C26H22N4O2, contains neither hydrogen bonds nor π...π short intermolecular contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007542/na6221sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007542/na6221Isup2.hkl
Contains datablock I

CCDC reference: 214600

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.056
  • wR factor = 0.151
  • Data-to-parameter ratio = 15.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) <H(6C)
Author response: ...The atoms are part of a disordered group and are in fact attached.
PLAT_305  Alert A Isolated Hydrogen Atom (Outside Bond Range ??)      <H(6D)
Author response: ...The atoms are part of a disordered group and are in fact attached.

Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(8) - H(8) ?
2 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Benzodiazepines are an important class of psychotherapeutic compounds. In recent years, some examples of heterocyclic rings fused to the seven-member diazepine ring system have been reported (Kelly et al., 1997, and references therein). In particular, good CNS activity was reported for various pyrazolodiazepines (DeWald et al., 1981). Some of these compounds are known to have activities as psychotropics (Chimirri et al., 1993, and references therein).

The diazepine ring in the title compound, (I), is disordered, with atom C6 taking up two possible sites. The major component has a site occupancy of 0.895 (7). There are no unusual bonds or angles nor are there any intermolecular contacts less than van der Waals radii.

Experimental top

Glacial acetic acid (1 ml) was added to a solution of 4,5-diamino-3-methyl-1-phenylpyrazole (3.2 mmol) and 1-(1,3-benzodioxol-5-yl)-3-phenyl-2-propen-1-one (3.2 mmol) in 10 ml absolute ethanol and then refluxed for 6 h (reaction monitored by TLC). The resulting precipitate was filtered, washed with ethanol, dried and recrystallized from ethanol to afford crystals suitable for X-ray diffraction. 90% yield. Mp. 450, Anal. Calcd. for C26H22N4O2: C, 73.92; H, 5.25; N, 13.26. Found: C, 73.96; H, 5.19; N, 13.15.

Refinement top

Molecule (I) crystallized in the triclinic system; space group P-1 assumed and confirmed by the analysis. H atoms were treated as riding atoms, with C—H 0.95 to 1.00 Å, N—H 0.88 Å. Atom C6A of the minor component was fixed at 1.520 (2) Å from atoms C5 and C7 by means of the DFIX command. Atoms C6 and C6A were constrained to have the same anisotropic displacement parameters by use of the EADP command.

Computing details top

Data collection: Kappa-CCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1976), PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A view of the major (top) and minor (bottom) components of (I), with our numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
5-(1,3-benzodioxol-5-yl)-3-methyl-1,7-diphenyl-1,6,7,8-tetrahydropyrazolo [3,4-b][1,4]diazepine top
Crystal data top
C26H22N4O2F(000) = 444
Mr = 422.48Dx = 1.379 Mg m3
Triclinic, P1Melting point: 450 K
a = 10.2608 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.9910 (6) ÅCell parameters from 4524 reflections
c = 11.2485 (8) Åθ = 3.0–27.4°
α = 63.656 (4)°µ = 0.09 mm1
β = 63.573 (3)°T = 120 K
γ = 77.080 (5)°Plate, orange
V = 1017.49 (12) Å30.20 × 0.20 × 0.05 mm
Z = 2
Data collection top
Kappa-CCD
diffractometer
4524 independent reflections
Radiation source: fine-focus sealed X-ray tube2909 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.094
ϕ scans and ω scans with κ offsetsθmax = 27.4°, θmin = 3.0°
Absorption correction: multi-scan
DENZO–SMN (Otwinowski & Minor, 1997)
h = 1313
Tmin = 0.982, Tmax = 0.996k = 1314
13871 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0677P)2 + 0.1359P]
where P = (Fo2 + 2Fc2)/3
4524 reflections(Δ/σ)max < 0.001
294 parametersΔρmax = 0.52 e Å3
2 restraintsΔρmin = 0.35 e Å3
Crystal data top
C26H22N4O2γ = 77.080 (5)°
Mr = 422.48V = 1017.49 (12) Å3
Triclinic, P1Z = 2
a = 10.2608 (8) ÅMo Kα radiation
b = 10.9910 (6) ŵ = 0.09 mm1
c = 11.2485 (8) ÅT = 120 K
α = 63.656 (4)°0.20 × 0.20 × 0.05 mm
β = 63.573 (3)°
Data collection top
Kappa-CCD
diffractometer
4524 independent reflections
Absorption correction: multi-scan
DENZO–SMN (Otwinowski & Minor, 1997)
2909 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.996Rint = 0.094
13871 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0562 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.04Δρmax = 0.52 e Å3
4524 reflectionsΔρmin = 0.35 e Å3
294 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.51087 (17)0.23431 (16)0.90014 (16)0.0294 (4)
C110.6064 (2)0.16187 (19)0.9717 (2)0.0291 (5)
C120.6770 (2)0.04204 (19)0.9611 (2)0.0316 (5)
C130.7669 (2)0.0258 (2)1.0345 (2)0.0359 (5)
C140.7838 (2)0.0222 (2)1.1202 (2)0.0391 (5)
C150.7110 (2)0.1409 (2)1.1322 (2)0.0401 (5)
C160.6230 (2)0.2118 (2)1.0574 (2)0.0346 (5)
N20.39136 (17)0.30282 (17)0.96710 (18)0.0346 (4)
C30.3252 (2)0.3606 (2)0.8773 (2)0.0332 (5)
C310.1895 (2)0.4450 (3)0.9127 (3)0.0478 (6)
C3A0.3972 (2)0.33116 (19)0.7528 (2)0.0279 (4)
N40.34511 (17)0.38207 (16)0.64429 (17)0.0298 (4)
C50.3889 (2)0.3398 (2)0.5430 (2)0.0328 (5)
C510.32212 (19)0.40531 (19)0.4356 (2)0.0290 (4)
C520.21902 (19)0.51283 (18)0.4483 (2)0.0274 (4)
C5A0.1560 (2)0.56986 (18)0.3512 (2)0.0273 (4)
O510.05687 (15)0.67723 (13)0.34120 (15)0.0372 (4)
C530.0234 (2)0.6973 (2)0.2232 (2)0.0353 (5)
O520.09884 (16)0.59358 (14)0.17073 (16)0.0422 (4)
C5B0.1836 (2)0.5229 (2)0.2479 (2)0.0314 (5)
C540.2832 (2)0.4202 (2)0.2307 (2)0.0398 (5)
C550.3525 (2)0.3631 (2)0.3270 (2)0.0368 (5)
C60.4934 (2)0.2180 (2)0.5394 (3)0.0332 (8)0.895 (7)
C6A0.5512 (4)0.3338 (15)0.4533 (6)0.0332 (8)0.10
C70.6373 (2)0.2323 (2)0.5380 (2)0.0397 (5)
C710.7602 (2)0.1501 (2)0.4678 (2)0.0346 (5)
C720.7480 (2)0.0116 (2)0.5135 (2)0.0401 (5)
C730.8610 (2)0.0641 (2)0.4488 (2)0.0410 (5)
C740.9865 (2)0.0011 (2)0.3388 (2)0.0394 (5)
C751.0000 (2)0.1352 (2)0.2935 (2)0.0419 (5)
C760.8870 (2)0.2102 (2)0.3582 (2)0.0402 (5)
N80.62696 (17)0.19241 (15)0.68393 (16)0.0290 (4)
C8A0.5175 (2)0.25056 (18)0.7706 (2)0.0269 (4)
H120.66390.00670.90400.038*
H130.81770.10691.02530.043*
H140.84500.02581.17100.047*
H150.72160.17411.19220.048*
H160.57420.29411.06470.042*
H31A0.15610.43671.01220.072*
H31B0.11400.41370.90280.072*
H31C0.20910.54020.84640.072*
H520.19460.54420.52220.033*
H53A0.05440.78790.14540.042*
H53B0.08280.69220.25570.042*
H540.30440.38910.15740.048*
H550.42360.29220.31720.044*
H6A0.45420.13390.62560.040*0.895 (7)
H6B0.51690.20290.45140.040*0.895 (7)
H6C0.57180.31240.36980.040*0.105 (7)
H6D0.59360.42320.41290.040*0.105 (7)
H70.66290.33010.48230.048*0.895 (7)
H7A0.70650.30450.50050.048*0.105 (7)
H720.66130.03170.59000.048*
H730.85170.15870.48010.049*
H741.06430.05230.29390.047*
H751.08720.17820.21770.050*
H760.89710.30470.32640.048*
H80.71270.18210.68780.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0264 (9)0.0400 (9)0.0272 (8)0.0088 (7)0.0128 (7)0.0201 (8)
C110.0242 (10)0.0378 (11)0.0239 (10)0.0031 (8)0.0102 (8)0.0123 (9)
C120.0294 (11)0.0379 (11)0.0274 (10)0.0009 (8)0.0118 (8)0.0131 (9)
C130.0327 (11)0.0364 (12)0.0325 (11)0.0054 (9)0.0142 (9)0.0102 (10)
C140.0346 (12)0.0526 (13)0.0308 (11)0.0072 (10)0.0194 (9)0.0145 (10)
C150.0363 (12)0.0586 (14)0.0329 (11)0.0045 (10)0.0175 (9)0.0232 (11)
C160.0319 (11)0.0444 (12)0.0318 (11)0.0068 (9)0.0139 (9)0.0209 (10)
N20.0300 (9)0.0486 (10)0.0346 (9)0.0152 (8)0.0164 (7)0.0282 (8)
C30.0323 (11)0.0411 (12)0.0350 (11)0.0095 (9)0.0179 (9)0.0228 (10)
C310.0451 (14)0.0672 (15)0.0476 (14)0.0278 (11)0.0274 (11)0.0409 (13)
C3A0.0280 (10)0.0326 (10)0.0285 (10)0.0062 (8)0.0136 (8)0.0173 (9)
N40.0269 (9)0.0375 (9)0.0302 (9)0.0063 (7)0.0142 (7)0.0182 (7)
C50.0273 (11)0.0450 (12)0.0336 (11)0.0090 (9)0.0156 (9)0.0228 (10)
C510.0235 (10)0.0382 (11)0.0285 (10)0.0038 (8)0.0111 (8)0.0172 (9)
C520.0268 (10)0.0329 (10)0.0279 (10)0.0012 (8)0.0117 (8)0.0167 (9)
C5A0.0243 (10)0.0267 (10)0.0304 (10)0.0024 (8)0.0104 (8)0.0127 (9)
O510.0398 (8)0.0388 (8)0.0402 (8)0.0147 (6)0.0240 (7)0.0209 (7)
C530.0329 (11)0.0401 (12)0.0356 (11)0.0083 (9)0.0183 (9)0.0166 (10)
O520.0482 (9)0.0490 (9)0.0464 (9)0.0187 (7)0.0335 (7)0.0274 (8)
C5B0.0319 (11)0.0371 (11)0.0317 (10)0.0048 (9)0.0188 (9)0.0156 (9)
C540.0465 (13)0.0504 (13)0.0371 (12)0.0146 (10)0.0246 (10)0.0288 (10)
C550.0368 (12)0.0454 (12)0.0362 (11)0.0164 (9)0.0199 (9)0.0256 (10)
C60.0307 (13)0.0417 (14)0.0368 (14)0.0077 (10)0.0168 (10)0.0241 (11)
C6A0.0307 (13)0.0417 (14)0.0368 (14)0.0077 (10)0.0168 (10)0.0241 (11)
C70.0388 (12)0.0553 (13)0.0364 (12)0.0185 (10)0.0212 (10)0.0305 (11)
C710.0387 (12)0.0436 (12)0.0329 (11)0.0166 (9)0.0235 (9)0.0236 (10)
C720.0319 (12)0.0542 (14)0.0329 (11)0.0071 (10)0.0114 (9)0.0213 (11)
C730.0417 (13)0.0427 (12)0.0454 (13)0.0125 (10)0.0225 (11)0.0243 (11)
C740.0338 (12)0.0530 (14)0.0381 (12)0.0199 (10)0.0180 (9)0.0296 (11)
C750.0356 (12)0.0517 (14)0.0397 (12)0.0087 (10)0.0151 (10)0.0237 (11)
C760.0435 (13)0.0428 (12)0.0422 (12)0.0116 (10)0.0232 (10)0.0231 (11)
N80.0234 (8)0.0415 (9)0.0272 (9)0.0092 (7)0.0127 (7)0.0198 (8)
C8A0.0264 (10)0.0314 (10)0.0266 (10)0.0028 (8)0.0110 (8)0.0157 (8)
Geometric parameters (Å, º) top
N1—C8A1.359 (2)C53—O521.429 (2)
N1—N21.381 (2)C53—H53A0.99
N1—C111.423 (2)C53—H53B0.99
C11—C121.382 (3)O52—C5B1.373 (2)
C11—C161.384 (3)C5B—C541.363 (3)
C12—C131.383 (3)C54—C551.398 (3)
C12—H120.95C54—H540.95
C13—C141.371 (3)C55—H550.95
C13—H130.95C6—C71.511 (3)
C14—C151.381 (3)C6—H6A0.99
C14—H140.95C6—H6B0.99
C15—C161.383 (3)C6A—C71.516 (2)
C15—H150.95C6A—H6B1.5664
C16—H160.95C6A—H6C0.99
N2—C31.316 (2)C6A—H6D0.99
C3—C3A1.410 (3)C6A—H71.3123
C3—C311.488 (3)C7—N81.458 (2)
C31—H31A0.98C7—C711.505 (3)
C31—H31B0.98C7—H71.00
C31—H31C0.98C7—H7A1.00
C3A—C8A1.387 (3)C71—C761.372 (3)
C3A—N41.389 (2)C71—C721.390 (3)
N4—C51.280 (2)C72—C731.386 (3)
C5—C511.480 (3)C72—H720.95
C5—C6A1.520 (2)C73—C741.375 (3)
C5—C61.521 (3)C73—H730.95
C51—C551.379 (3)C74—C751.370 (3)
C51—C521.411 (3)C74—H740.95
C52—C5A1.358 (3)C75—C761.381 (3)
C52—H520.95C75—H750.95
C5A—C5B1.368 (3)C76—H760.95
C5A—O511.374 (2)N8—C8A1.370 (2)
O51—C531.428 (2)N8—H80.88
C8A—N1—N2111.69 (14)C51—C55—C54122.87 (18)
C8A—N1—C11130.40 (16)C51—C55—H55118.6
N2—N1—C11117.90 (15)C54—C55—H55118.6
C12—C11—C16120.35 (17)C7—C6—C5114.19 (19)
C12—C11—N1121.38 (18)C7—C6—H6A103.9
C16—C11—N1118.23 (17)C5—C6—H6A112.5
C11—C12—C13119.2 (2)C7—C6—H6B106.3
C11—C12—H12120.4C5—C6—H6B110.3
C13—C12—H12120.4H6A—C6—H6B109.3
C14—C13—C12120.99 (19)C7—C6A—C5114.0 (2)
C14—C13—H13119.5C7—C6A—H6B82.2
C12—C13—H13119.5C5—C6A—H6B84.9
C13—C14—C15119.45 (18)C7—C6A—H6C107.8
C13—C14—H14120.3C5—C6A—H6C112.1
C15—C14—H14120.3H6B—C6A—H6C50.7
C14—C15—C16120.5 (2)C7—C6A—H6D106.0
C14—C15—H15119.8C5—C6A—H6D110.2
C16—C15—H15119.8H6B—C6A—H6D156.9
C15—C16—C11119.45 (19)H6C—C6A—H6D106.3
C15—C16—H16120.3C7—C6A—H740.6
C11—C16—H16120.3C5—C6A—H7130.1
C3—N2—N1104.67 (15)H6B—C6A—H7118.7
N2—C3—C3A112.27 (16)H6C—C6A—H7116.7
N2—C3—C31120.55 (18)H6D—C6A—H765.4
C3A—C3—C31127.18 (18)N8—C7—C71108.09 (15)
C3—C31—H31A109.5N8—C7—C6111.23 (18)
C3—C31—H31B109.5C71—C7—C6113.35 (18)
H31A—C31—H31B109.5N8—C7—C6A132.8 (5)
C3—C31—H31C109.5C71—C7—C6A119.1 (5)
H31A—C31—H31C109.5C6—C7—C6A50.1 (5)
H31B—C31—H31C109.5N8—C7—H7108.0
C8A—C3A—N4133.61 (17)C71—C7—H7108.0
C8A—C3A—C3104.84 (17)C6—C7—H7108.0
N4—C3A—C3121.55 (16)C6A—C7—H758.7
C5—N4—C3A124.19 (16)N8—C7—H7A90.2
N4—C5—C51117.32 (17)C71—C7—H7A90.1
N4—C5—C6A119.0 (7)C6—C7—H7A139.5
C51—C5—C6A104.6 (3)C6A—C7—H7A90.0
N4—C5—C6122.20 (18)H7—C7—H7A31.5
C51—C5—C6120.18 (18)C76—C71—C72118.61 (19)
C6A—C5—C649.9 (5)C76—C71—C7120.7 (2)
C55—C51—C52118.71 (17)C72—C71—C7120.7 (2)
C55—C51—C5123.01 (17)C73—C72—C71120.7 (2)
C52—C51—C5118.25 (17)C73—C72—H72119.6
C5A—C52—C51117.66 (17)C71—C72—H72119.6
C5A—C52—H52121.2C74—C73—C72119.4 (2)
C51—C52—H52121.2C74—C73—H73120.3
C52—C5A—C5B122.59 (17)C72—C73—H73120.3
C52—C5A—O51127.33 (18)C75—C74—C73120.4 (2)
C5B—C5A—O51110.08 (16)C75—C74—H74119.8
C5A—O51—C53105.67 (14)C73—C74—H74119.8
O51—C53—O52108.25 (15)C74—C75—C76120.0 (2)
O51—C53—H53A110.0C74—C75—H75120.0
O52—C53—H53A110.0C76—C75—H75120.0
O51—C53—H53B110.0C71—C76—C75120.9 (2)
O52—C53—H53B110.0C71—C76—H76119.5
H53A—C53—H53B108.4C75—C76—H76119.5
C5B—O52—C53105.54 (15)C8A—N8—C7118.18 (15)
C54—C5B—C5A121.72 (17)C8A—N8—H8116.6
C54—C5B—O52128.07 (18)C7—N8—H8112.7
C5A—C5B—O52110.21 (16)N1—C8A—N8122.35 (16)
C5B—C54—C55116.35 (19)N1—C8A—C3A106.52 (16)
C5B—C54—H54121.8N8—C8A—C3A131.12 (18)
C55—C54—H54121.8
C8A—N1—C11—C1235.1 (3)C5A—C5B—C54—C551.7 (3)
N2—N1—C11—C12146.04 (18)O52—C5B—C54—C55178.46 (19)
C8A—N1—C11—C16147.4 (2)C52—C51—C55—C541.5 (3)
N2—N1—C11—C1631.5 (3)C5—C51—C55—C54176.3 (2)
C16—C11—C12—C131.4 (3)C5B—C54—C55—C510.9 (3)
N1—C11—C12—C13178.97 (17)N4—C5—C6—C758.5 (3)
C11—C12—C13—C141.7 (3)C51—C5—C6—C7127.9 (2)
C12—C13—C14—C150.7 (3)C6A—C5—C6—C744.2 (7)
C13—C14—C15—C160.7 (3)N4—C5—C6A—C765.3 (14)
C14—C15—C16—C111.0 (3)C51—C5—C6A—C7161.3 (10)
C12—C11—C16—C150.1 (3)C6—C5—C6A—C743.9 (7)
N1—C11—C16—C15177.72 (18)C5—C6—C7—N884.6 (2)
C8A—N1—N2—C30.2 (2)C5—C6—C7—C71153.36 (18)
C11—N1—N2—C3179.26 (17)C5—C6—C7—C6A44.1 (7)
N1—N2—C3—C3A0.5 (2)C5—C6A—C7—N838.4 (18)
N1—N2—C3—C31179.87 (19)C5—C6A—C7—C71141.3 (9)
N2—C3—C3A—C8A1.0 (2)C5—C6A—C7—C644.1 (7)
C31—C3—C3A—C8A179.5 (2)N8—C7—C71—C76109.6 (2)
N2—C3—C3A—N4179.91 (18)C6—C7—C71—C76126.7 (2)
C31—C3—C3A—N40.3 (3)C6A—C7—C71—C7670.7 (7)
C8A—C3A—N4—C514.6 (3)N8—C7—C71—C7269.9 (2)
C3—C3A—N4—C5166.59 (19)C6—C7—C71—C7253.8 (3)
C3A—N4—C5—C51179.92 (17)C6A—C7—C71—C72109.8 (7)
C3A—N4—C5—C6A52.3 (5)C76—C71—C72—C730.7 (3)
C3A—N4—C5—C66.3 (3)C7—C71—C72—C73179.84 (18)
N4—C5—C51—C55175.53 (19)C71—C72—C73—C740.4 (3)
C6A—C5—C51—C5550.1 (8)C72—C73—C74—C750.0 (3)
C6—C5—C51—C551.6 (3)C73—C74—C75—C760.2 (3)
N4—C5—C51—C522.3 (3)C72—C71—C76—C750.5 (3)
C6A—C5—C51—C52132.1 (8)C7—C71—C76—C75179.99 (18)
C6—C5—C51—C52176.22 (18)C74—C75—C76—C710.1 (3)
C55—C51—C52—C5A0.6 (3)C71—C7—N8—C8A177.23 (17)
C5—C51—C52—C5A178.47 (17)C6—C7—N8—C8A52.2 (2)
C51—C52—C5A—C5B3.2 (3)C6A—C7—N8—C8A2.5 (9)
C51—C52—C5A—O51178.03 (17)N2—N1—C8A—N8179.77 (16)
C52—C5A—O51—C53179.47 (19)C11—N1—C8A—N80.8 (3)
C5B—C5A—O51—C530.6 (2)N2—N1—C8A—C3A0.8 (2)
C5A—O51—C53—O523.5 (2)C11—N1—C8A—C3A179.71 (18)
O51—C53—O52—C5B5.1 (2)C7—N8—C8A—N1170.78 (18)
C52—C5A—C5B—C543.9 (3)C7—N8—C8A—C3A9.9 (3)
O51—C5A—C5B—C54177.14 (19)N4—C3A—C8A—N1180.0 (2)
C52—C5A—C5B—O52176.24 (17)C3—C3A—C8A—N11.0 (2)
O51—C5A—C5B—O522.7 (2)N4—C3A—C8A—N80.6 (4)
C53—O52—C5B—C54175.1 (2)C3—C3A—C8A—N8179.6 (2)
C53—O52—C5B—C5A4.8 (2)

Experimental details

Crystal data
Chemical formulaC26H22N4O2
Mr422.48
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)10.2608 (8), 10.9910 (6), 11.2485 (8)
α, β, γ (°)63.656 (4), 63.573 (3), 77.080 (5)
V3)1017.49 (12)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.20 × 0.05
Data collection
DiffractometerKappa-CCD
diffractometer
Absorption correctionMulti-scan
DENZO–SMN (Otwinowski & Minor, 1997)
Tmin, Tmax0.982, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
13871, 4524, 2909
Rint0.094
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.151, 1.04
No. of reflections4524
No. of parameters294
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.52, 0.35

Computer programs: Kappa-CCD Server Software (Nonius, 1997), DENZO–SMN (Otwinowski & Minor, 1997), DENZO–SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP (Johnson, 1976), PLATON (Spek, 2003), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
N1—C8A1.359 (2)N4—C51.280 (2)
N1—N21.381 (2)C5—C61.521 (3)
N2—C31.316 (2)C6—C71.511 (3)
C3—C3A1.410 (3)C7—N81.458 (2)
C3A—N41.389 (2)N8—C8A1.370 (2)
C8A—N1—N2111.69 (14)N4—C5—C6122.20 (18)
C3—N2—N1104.67 (15)C7—C6—C5114.19 (19)
N2—C3—C3A112.27 (16)N8—C7—C6111.23 (18)
C8A—C3A—N4133.61 (17)C8A—N8—C7118.18 (15)
C8A—C3A—C3104.84 (17)N1—C8A—N8122.35 (16)
N4—C3A—C3121.55 (16)N1—C8A—C3A106.52 (16)
C5—N4—C3A124.19 (16)N8—C8A—C3A131.12 (18)
C8A—N1—C11—C1235.1 (3)C6—C5—C51—C551.6 (3)
N2—N1—C11—C12146.04 (18)N4—C5—C51—C522.3 (3)
C8A—N1—C11—C16147.4 (2)N8—C7—C71—C76109.6 (2)
N2—N1—C11—C1631.5 (3)C6—C7—C71—C76126.7 (2)
N4—C5—C51—C55175.53 (19)N8—C7—C71—C7269.9 (2)
C6A—C5—C51—C5550.1 (8)C6—C7—C71—C7253.8 (3)
 

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