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In the title compounds, C17H15N3 and C20H22N4, the methyl derivative crystallizes with two mol­ecules in the asymmetric unit, while the N,N-diethyl­amino derivative crystallizes with one mol­ecule per asymmetric unit. The bi­phenyl twist angle for both mol­ecular structures is approximately 45°. The molecular packing is stabilized by N—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101002128/bj1022sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101002128/bj1022Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101002128/bj1022IIsup3.hkl
Contains datablock II

CCDC references: 166980; 166981

Comment top

Biphenyl derivatives have been extensively studied in the past because of the difference found in the torsion angle between aromatic rings which determines the photophysical, biological and laser activities (Shukla et al., 1985; Nieger et al., 1998). The laser activity of the biphenyl compound can be enhanced by bulkier substitutions on the phenyl rings which cause deviations from coplanarity. The π electron delocalization along the biphenyl unit will be the maximum in the coplanar arrangement of the biphenyls (Nieger et al., 1998). Apart from the photophysical properties, biphenyl compounds are of great importance due to the activity of these molecules on the central nervous system (Reboul et al., 1993). Certain fluoro-substituted biphenyl derivatives have greater affinities to certain receptor proteins (Mckinney & Singh, 1988). The present study is a part of a series of investigations on the crystal structures of biphenyl derivatives. \sch

Compound (I) contains two molecules in the asymmetric unit, designated (Ia) and (Ib). Figure 1 shows the displacement ellipsoids and atom labelling scheme for (Ia) and (Ib). Compound (II) contains one molecule per asymmetric unit, and Figure 2 shows the displacement ellipsoids and atom labelling for (II). The dihedral angles between phenyl rings A and B are 44.1 (1) and 46.7 (1)°, respectively. In (II), the dihedral angle between the phenyl rings is 42.1 (1)°. The twisting of these rings can also be described using the following inter-ring torsion angles: C6A—C1A—C1A'-C6A' = -40.5 (3)° and C6B—C1B—C1B'-C6B' = -42.9 (3)° for (I); C6—C1—C1'-C6' = 43.8 (3)° for (II). The values of the torsion angles C2'-C1A'-C1A—C6A [136.7 (2)°], C2B'-C1B'-C1B—C6B [135.0 (2)°] in (I) and C2'-C1'-C1—C6 [-131.4 (2)°] in (II) indicate that the conformation of both molecules (Ia) and (Ib) is +anticlinal and that of (II) is -anticlinal. The carbon atom C7 significantly deviates from the mean plane of ring A by -0.050 (2) Å in (Ia) and -0.105 (3) Å in (Ib) and 0.158 (2) Å in compound (II). The bond lengths and bond angles for compounds (I) and (II) are listed in Tables 1 and 3, respectively. The triple bond distances N3—C8 and C7—N2 agree with the literature values [1.138 (7) Å] (Allen et al., 1986). The bond angles around C8 and C7 satisfy the triple-bond character of C8—N3 and C7—N2 (sp hybridization). The ring-ring bond distances which connect the two phenyl rings A and B are comparable with the reported values [1.487 (7) Å] (Allen et al., 1986). The ethyl substituent on the A ring in (I) and (II) are twisted out of the plane of the ring as evidenced by the C6—C5—C9—C10 torsion angle. This angle has values of 33.2 (6)° and 96.6 (3)° for (Ia) and (Ib), respectively, and 94.5 (3)° for (II). The diethyl substituent in (II) attached to the phenyl ring B is completely staggered. The sum of the angles around N4 in compound (II) is 360° and is an indicative of the sp2 hybridization.

The inter-ring bond distance in unsubstituted biphenyl is found to be 1.507 Å (Trotter, 1961). The inter-ring bond distances [C1A—C1A', C1B—C1B' in (I) and C1—C1' in (II)] are 1.485 (3), 1.484 (3) and 1.480 (3) Å, respectively. These values agree well with those of related structures found in polychlorinated biphenyl [1.485 (6) Å; Mackinney & Singh, 1981], 2-Fluorobiphenyl [1.483 (4) Å; Rajnikant et al., 1995] and the theoretically calculated value of 1.488 Å between two sp2-hybridized carbon atoms (Dewar & Schmeizing, 1968).

Apart from the normal van der Waals interaction, the packing of the crystal is stabilized by intermolecular N—H···N hydrogen bonds. The hydrogen-bonding geometries for (I) and (II) are given in Tables 2 and 4, respectively. In both structures, the nitrogen atom of the cyano group participates in the hydrogen-bonded interaction as an acceptor atom. All N—H···N interactions have distances less than the sum of their van der Waals radii (Bondi, 1964). The molecular packing arrangement in compound (I) down the a axis is characterized by an intermolecular N—H···N hydrogen bond between (Ia) and (Ib), with N1B···N3A distance of 3.166 (3) Å, and two N—H···N intermolecular interactions with the molecules related by inversion, having donar-acceptor distances of 3.228 (3) and 3.157 (3) Å. It is a layered structure, with the layers parallel to bc plane. In structure (II), the crystal packing is stabilized by two intermolecular hydrogen bonds.: N1···N2i = 3.259 (2) Å and N1···N3ii = 3.006 (2) Å·[Symmetry codes: (i) 2 - x, 1/2 + y, 1/2 - z; (ii) 2 - x, -1/2 + y, 1/2 - z.] Each molecule mutually donates and accepts two protons with symmetry-related molecules.

Related literature top

For related literature, see: Allen et al. (1986); Bondi (1964); Dewar & Schmeising (1968); Nieger et al. (1998); Rajnikant, Watkin & Tranter (1995); Reboul et al. (1993); Shukla et al. (1985); Trotter (1961).

Experimental top

The title compounds were synthesized as follows: a mixture of 5-(4-methylphenyl)-pent-4-en-3-one (1.0 g, 5.74 mmol), malononitrile (0.76 g, 11.51 mmol) and catalytic amount of pyrrolidine in ethanol (20 ml) for comound I and a mixture of 5-(4-diethylaminophenyl)-pent-4-en-3-one (1.0 g, 4.6 mmol), malononitrile (0.29 g, 4.39 mmol) and catalytic amount of pyrrolidine in ethanol (20 ml) for compound (II), respectively, were taken as starting materials. The mixtures were heated under reflux for 7 h, concentrated under reduced pressure and purified by column chromatography over silica gel. Elution with a mixture of petroleum ether-benzene (1:5) gave the product as a yellow solid. The compounds were dissolved in ethyl acetate with few drops of hexane. Slow evaporation of the solvent at room temperature produced crystals from which experimental samples were obtained.

Computing details top

For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. Molecular structure of the compound (I) with the 50% probability displacement ellipsoids. Hydrogen atoms omitted for clarity.
[Figure 2] Fig. 2. Molecular structure of the compound (II) with the 50% probability displacement ellipsoids. Hydrogen atoms omitted for clarity.
(I) 3-amino-2,4 dicyano-5-ethyl-4'- methyl Biphenyl top
Crystal data top
C17H15N3F(000) = 664
Mr = 261.32Dx = 1.216 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.8579 (1) ÅCell parameters from 8192 reflections
b = 23.7627 (5) Åθ = 1.5–28.3°
c = 15.3423 (2) ŵ = 0.07 mm1
β = 94.765 (1)°T = 293 K
V = 2854.89 (8) Å3Rectangular, pale yellow
Z = 80.30 × 0.24 × 0.14 mm
Data collection top
Siemens SMART CCD area detector
diffractometer
6961 independent reflections
Radiation source: fine-focus sealed tube3077 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.090
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 1.6°
ω scansh = 1010
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 3131
Tmin = 0.978, Tmax = 0.990l = 1020
19861 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)] = 0.067H-atom parameters constrained
wR(F2) = 0.173 w = 1/[σ2(Fo2) + (0.0504P)2 + 0.0465P]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
6961 reflectionsΔρmax = 0.32 e Å3
365 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: none
Crystal data top
C17H15N3V = 2854.89 (8) Å3
Mr = 261.32Z = 8
Monoclinic, P21/cMo Kα radiation
a = 7.8579 (1) ŵ = 0.07 mm1
b = 23.7627 (5) ÅT = 293 K
c = 15.3423 (2) Å0.30 × 0.24 × 0.14 mm
β = 94.765 (1)°
Data collection top
Siemens SMART CCD area detector
diffractometer
6961 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
3077 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.990Rint = 0.090
19861 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.173H-atom parameters constrained
S = 0.97Δρmax = 0.32 e Å3
6961 reflectionsΔρmin = 0.30 e Å3
365 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.1068 (3)0.60919 (8)0.46133 (13)0.0537 (6)
H1A10.08570.57370.45910.064*
H1A20.08400.62980.41580.064*
N2A0.1276 (3)0.74519 (9)0.40063 (14)0.0564 (6)
N3A0.1427 (3)0.49363 (9)0.60111 (15)0.0701 (7)
C1A'0.3287 (3)0.77552 (9)0.62858 (15)0.0362 (6)
C2A'0.4072 (3)0.80462 (9)0.56434 (16)0.0403 (6)
H2A'0.43150.78630.51330.048*
C3A'0.4492 (3)0.86090 (10)0.57616 (17)0.0462 (6)
H3A'0.50240.87970.53280.055*
C4A'0.4142 (3)0.88966 (10)0.6507 (2)0.0510 (7)
C5A'0.3381 (3)0.86051 (11)0.71425 (19)0.0540 (7)
H5A'0.31470.87890.76540.065*
C6A'0.2957 (3)0.80439 (10)0.70374 (16)0.0452 (6)
H6A'0.24420.78570.74790.054*
C1A0.2871 (3)0.71471 (9)0.62019 (14)0.0351 (5)
C2A0.2159 (3)0.69041 (9)0.54184 (14)0.0334 (5)
C3A0.1760 (3)0.63275 (9)0.53688 (15)0.0368 (6)
C4A0.2138 (3)0.59952 (9)0.61184 (16)0.0401 (6)
C5A0.2864 (3)0.62302 (10)0.69014 (16)0.0456 (6)
C6A0.3203 (3)0.67982 (9)0.69284 (15)0.0430 (6)
H6A0.36710.69550.74490.052*
C7A0.1699 (3)0.72288 (9)0.46506 (16)0.0392 (6)
C8A0.1736 (3)0.54050 (11)0.60650 (16)0.0488 (7)
C9A0.3286 (5)0.58558 (11)0.76820 (18)0.0751 (10)
H9A10.25370.55310.76220.090*
H9A20.44430.57190.76500.090*
C10A0.3181 (9)0.60692 (17)0.8489 (2)0.181 (3)
H10A0.41590.63020.86430.271*
H10B0.31480.57670.89030.271*
H10C0.21600.62910.84970.271*
C11A0.4596 (4)0.95143 (11)0.6617 (2)0.0815 (10)
H11A0.53970.95610.71200.122*
H11B0.35810.97270.66970.122*
H11C0.50970.96460.61050.122*
N1B0.1944 (3)0.37256 (9)0.68535 (13)0.0560 (6)
H1B10.16660.40740.67890.067*
H1B20.23500.35450.64320.067*
N2B0.3510 (3)0.24409 (10)0.64279 (15)0.0637 (7)
N3B0.0110 (4)0.47704 (10)0.80857 (17)0.0784 (8)
C1B'0.2250 (3)0.19896 (9)0.86189 (15)0.0385 (6)
C2B'0.1694 (3)0.16080 (10)0.79714 (17)0.0483 (7)
H2B'0.10920.17360.74630.058*
C3B'0.2025 (3)0.10379 (10)0.80748 (18)0.0527 (7)
H3B'0.16460.07900.76320.063*
C4B'0.2906 (3)0.08320 (10)0.88208 (17)0.0483 (7)
C5B'0.3420 (3)0.12094 (11)0.94698 (17)0.0509 (7)
H5B'0.40010.10780.99820.061*
C6B'0.3096 (3)0.17788 (10)0.93815 (15)0.0446 (6)
H6B'0.34470.20230.98350.054*
C1B0.1905 (3)0.26010 (9)0.85158 (16)0.0382 (6)
C2B0.2149 (3)0.28828 (9)0.77364 (15)0.0374 (6)
C3B0.1739 (3)0.34595 (10)0.76246 (16)0.0403 (6)
C4B0.1081 (3)0.37396 (10)0.83261 (17)0.0420 (6)
C5B0.0889 (3)0.34729 (10)0.91243 (16)0.0421 (6)
C6B0.1330 (3)0.29067 (10)0.92039 (16)0.0424 (6)
H6B0.12360.27270.97360.051*
C7B0.2900 (3)0.26140 (10)0.70208 (17)0.0441 (6)
C8B0.0544 (3)0.43156 (12)0.82023 (18)0.0536 (7)
C9B0.0220 (4)0.37831 (11)0.98761 (18)0.0581 (7)
H9B10.02920.35141.02520.070*
H9B20.06700.40400.96500.070*
C10B0.1573 (5)0.41131 (15)1.0417 (2)0.1059 (13)
H10D0.24640.38631.06400.159*
H10E0.10710.42911.08950.159*
H10F0.20420.43951.00580.159*
C11B0.3303 (4)0.02109 (10)0.8916 (2)0.0704 (9)
H11D0.24700.00020.85610.106*
H11E0.32740.01020.95170.106*
H11F0.44190.01380.87300.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0831 (17)0.0316 (11)0.0438 (13)0.0042 (11)0.0103 (11)0.0059 (10)
N2A0.0791 (17)0.0526 (14)0.0362 (13)0.0033 (12)0.0027 (12)0.0036 (11)
N3A0.112 (2)0.0334 (13)0.0649 (16)0.0128 (13)0.0044 (14)0.0010 (12)
C1A'0.0378 (13)0.0340 (13)0.0355 (14)0.0009 (10)0.0041 (11)0.0000 (11)
C2A'0.0447 (14)0.0350 (14)0.0405 (14)0.0007 (11)0.0009 (11)0.0011 (11)
C3A'0.0469 (15)0.0360 (14)0.0544 (17)0.0055 (11)0.0029 (12)0.0096 (13)
C4A'0.0491 (16)0.0308 (14)0.071 (2)0.0031 (12)0.0065 (14)0.0052 (14)
C5A'0.0574 (17)0.0427 (16)0.0614 (19)0.0005 (13)0.0015 (14)0.0199 (14)
C6A'0.0510 (16)0.0422 (15)0.0423 (15)0.0031 (12)0.0029 (12)0.0053 (12)
C1A0.0408 (13)0.0296 (12)0.0347 (13)0.0032 (10)0.0020 (11)0.0020 (11)
C2A0.0395 (13)0.0295 (12)0.0312 (13)0.0000 (10)0.0018 (10)0.0007 (10)
C3A0.0441 (14)0.0295 (12)0.0363 (14)0.0018 (10)0.0004 (11)0.0025 (11)
C4A0.0523 (15)0.0261 (13)0.0417 (15)0.0035 (11)0.0036 (12)0.0006 (11)
C5A0.0633 (17)0.0349 (14)0.0387 (15)0.0039 (12)0.0043 (12)0.0056 (12)
C6A0.0609 (17)0.0345 (14)0.0321 (13)0.0067 (12)0.0063 (12)0.0002 (11)
C7A0.0515 (15)0.0292 (13)0.0366 (14)0.0012 (11)0.0013 (12)0.0076 (11)
C8A0.0679 (18)0.0359 (16)0.0424 (15)0.0046 (13)0.0041 (13)0.0027 (12)
C9A0.133 (3)0.0477 (17)0.0431 (18)0.0021 (18)0.0010 (18)0.0136 (15)
C10A0.405 (9)0.090 (3)0.044 (2)0.055 (4)0.001 (4)0.012 (2)
C11A0.085 (2)0.0386 (17)0.119 (3)0.0115 (15)0.003 (2)0.0138 (17)
N1B0.0836 (17)0.0418 (12)0.0423 (13)0.0087 (11)0.0035 (12)0.0097 (10)
N2B0.0831 (18)0.0686 (17)0.0399 (14)0.0123 (13)0.0077 (13)0.0009 (12)
N3B0.096 (2)0.0473 (16)0.093 (2)0.0137 (14)0.0162 (16)0.0062 (15)
C1B'0.0430 (14)0.0363 (13)0.0364 (14)0.0042 (11)0.0035 (11)0.0037 (11)
C2B'0.0557 (17)0.0434 (16)0.0445 (15)0.0035 (12)0.0031 (13)0.0047 (12)
C3B'0.0676 (19)0.0388 (15)0.0510 (17)0.0082 (13)0.0010 (14)0.0040 (13)
C4B'0.0595 (17)0.0365 (14)0.0506 (17)0.0023 (12)0.0151 (14)0.0055 (13)
C5B'0.0647 (18)0.0458 (16)0.0422 (16)0.0013 (13)0.0045 (13)0.0144 (13)
C6B'0.0574 (16)0.0409 (15)0.0356 (14)0.0044 (12)0.0036 (12)0.0025 (12)
C1B0.0385 (13)0.0368 (13)0.0385 (14)0.0033 (11)0.0025 (11)0.0001 (12)
C2B0.0416 (14)0.0361 (13)0.0336 (14)0.0014 (11)0.0016 (11)0.0006 (11)
C3B0.0425 (14)0.0383 (14)0.0387 (15)0.0025 (11)0.0045 (11)0.0051 (12)
C4B0.0408 (14)0.0335 (13)0.0509 (16)0.0013 (11)0.0006 (12)0.0004 (12)
C5B0.0390 (14)0.0407 (14)0.0468 (15)0.0049 (11)0.0050 (12)0.0048 (12)
C6B0.0461 (15)0.0443 (15)0.0369 (14)0.0051 (12)0.0045 (11)0.0017 (12)
C7B0.0551 (16)0.0423 (15)0.0342 (15)0.0023 (12)0.0011 (12)0.0070 (12)
C8B0.0556 (17)0.0441 (17)0.0607 (19)0.0019 (13)0.0035 (14)0.0001 (14)
C9B0.0662 (19)0.0519 (17)0.0583 (18)0.0047 (14)0.0187 (15)0.0092 (14)
C10B0.099 (3)0.136 (3)0.083 (3)0.005 (2)0.015 (2)0.064 (2)
C11B0.094 (2)0.0434 (17)0.076 (2)0.0088 (15)0.0193 (18)0.0100 (15)
Geometric parameters (Å, º) top
N1A—C3A1.360 (3)N1B—C3B1.363 (3)
N1A—H1A10.8600N1B—H1B10.8600
N1A—H1A20.8600N1B—H1B20.8600
N2A—C7A1.146 (3)N2B—C7B1.140 (3)
N3A—C8A1.141 (3)N3B—C8B1.143 (3)
C1A'—C2A'1.390 (3)C1B'—C6B'1.390 (3)
C1A'—C6A'1.385 (3)C1B'—C2B'1.389 (3)
C1A'—C1A1.485 (3)C1B'—C1B1.484 (3)
C2A'—C3A'1.386 (3)C2B'—C3B'1.386 (3)
C2A'—H2A'0.9300C2B'—H2B'0.9300
C3A'—C4A'1.379 (4)C3B'—C4B'1.377 (4)
C3A'—H3A'0.9300C3B'—H3B'0.9300
C4A'—C5A'1.373 (4)C4B'—C5B'1.376 (3)
C4A'—C11A1.517 (3)C4B'—C11B1.513 (3)
C5A'—C6A'1.381 (3)C5B'—C6B'1.381 (3)
C5A'—H5A'0.9300C5B'—H5B'0.9300
C6A'—H6A'0.9300C6B'—H6B'0.9300
C1A—C6A1.396 (3)C1B—C6B1.388 (3)
C1A—C2A1.407 (3)C1B—C2B1.398 (3)
C2A—C3A1.406 (3)C2B—C3B1.415 (3)
C2A—C7A1.429 (3)C2B—C7B1.438 (3)
C3A—C4A1.406 (3)C3B—C4B1.400 (3)
C4A—C5A1.402 (3)C4B—C5B1.398 (3)
C4A—C8A1.438 (3)C4B—C8B1.440 (4)
C5A—C6A1.376 (3)C5B—C6B1.392 (3)
C5A—C9A1.507 (3)C5B—C9B1.500 (3)
C6A—H6A0.9300C6B—H6B0.9300
C9A—C10A1.347 (4)C9B—C10B1.512 (4)
C9A—H9A10.9700C9B—H9B10.9700
C9A—H9A20.9700C9B—H9B20.9700
C10A—H10A0.9600C10B—H10D0.9600
C10A—H10B0.9600C10B—H10E0.9600
C10A—H10C0.9600C10B—H10F0.9600
C11A—H11A0.9600C11B—H11D0.9600
C11A—H11B0.9600C11B—H11E0.9600
C11A—H11C0.9600C11B—H11F0.9600
C3A—N1A—H1A1120.0C3B—N1B—H1B1120.0
C3A—N1A—H1A2120.0C3B—N1B—H1B2120.0
H1A1—N1A—H1A2120.0H1B1—N1B—H1B2120.0
C2A'—C1A'—C6A'118.0 (2)C6B'—C1B'—C2B'117.8 (2)
C2A'—C1A'—C1A122.0 (2)C6B'—C1B'—C1B120.9 (2)
C6A'—C1A'—C1A120.0 (2)C2B'—C1B'—C1B121.3 (2)
C1A'—C2A'—C3A'120.2 (2)C3B'—C2B'—C1B'120.8 (2)
C1A'—C2A'—H2A'119.9C3B'—C2B'—H2B'119.6
C3A'—C2A'—H2A'119.9C1B'—C2B'—H2B'119.6
C4A'—C3A'—C2A'121.7 (2)C4B'—C3B'—C2B'121.3 (2)
C4A'—C3A'—H3A'119.2C4B'—C3B'—H3B'119.4
C2A'—C3A'—H3A'119.2C2B'—C3B'—H3B'119.4
C3A'—C4A'—C5A'117.9 (2)C3B'—C4B'—C5B'117.8 (2)
C3A'—C4A'—C11A120.7 (3)C3B'—C4B'—C11B120.8 (2)
C5A'—C4A'—C11A121.4 (3)C5B'—C4B'—C11B121.3 (2)
C6A'—C5A'—C4A'121.3 (2)C4B'—C5B'—C6B'121.8 (2)
C6A'—C5A'—H5A'119.4C4B'—C5B'—H5B'119.1
C4A'—C5A'—H5A'119.4C6B'—C5B'—H5B'119.1
C5A'—C6A'—C1A'121.1 (2)C5B'—C6B'—C1B'120.5 (2)
C5A'—C6A'—H6A'119.5C5B'—C6B'—H6B'119.8
C1A'—C6A'—H6A'119.5C1B'—C6B'—H6B'119.8
C6A—C1A—C2A118.2 (2)C6B—C1B—C2B118.5 (2)
C6A—C1A—C1A'118.9 (2)C6B—C1B—C1B'120.0 (2)
C2A—C1A—C1A'122.85 (19)C2B—C1B—C1B'121.6 (2)
C1A—C2A—C3A121.1 (2)C1B—C2B—C3B121.4 (2)
C1A—C2A—C7A122.55 (19)C1B—C2B—C7B122.3 (2)
C3A—C2A—C7A116.2 (2)C3B—C2B—C7B116.2 (2)
N1A—C3A—C4A120.6 (2)C4B—C3B—N1B121.6 (2)
N1A—C3A—C2A121.3 (2)C4B—C3B—C2B117.5 (2)
C4A—C3A—C2A118.2 (2)N1B—C3B—C2B120.9 (2)
C3A—C4A—C5A121.3 (2)C3B—C4B—C5B122.1 (2)
C3A—C4A—C8A118.1 (2)C3B—C4B—C8B118.2 (2)
C5A—C4A—C8A120.6 (2)C5B—C4B—C8B119.6 (2)
C6A—C5A—C4A118.7 (2)C4B—C5B—C6B118.1 (2)
C6A—C5A—C9A121.7 (2)C4B—C5B—C9B121.4 (2)
C4A—C5A—C9A119.5 (2)C6B—C5B—C9B120.5 (2)
C5A—C6A—C1A122.4 (2)C1B—C6B—C5B122.2 (2)
C5A—C6A—H6A118.8C1B—C6B—H6B118.9
C1A—C6A—H6A118.8C5B—C6B—H6B118.9
N2A—C7A—C2A174.7 (2)N2B—C7B—C2B174.8 (3)
N3A—C8A—C4A179.0 (3)N3B—C8B—C4B178.6 (3)
C10A—C9A—C5A118.8 (3)C5B—C9B—C10B113.7 (2)
C10A—C9A—H9A1107.6C5B—C9B—H9B1108.8
C5A—C9A—H9A1107.6C10B—C9B—H9B1108.8
C10A—C9A—H9A2107.6C5B—C9B—H9B2108.8
C5A—C9A—H9A2107.6C10B—C9B—H9B2108.8
H9A1—C9A—H9A2107.0H9B1—C9B—H9B2107.7
C9A—C10A—H10A109.5C9B—C10B—H10D109.5
C9A—C10A—H10B109.5C9B—C10B—H10E109.5
H10A—C10A—H10B109.5H10D—C10B—H10E109.5
C9A—C10A—H10C109.5C9B—C10B—H10F109.5
H10A—C10A—H10C109.5H10D—C10B—H10F109.5
H10B—C10A—H10C109.5H10E—C10B—H10F109.5
C4A'—C11A—H11A109.5C4B'—C11B—H11D109.5
C4A'—C11A—H11B109.5C4B'—C11B—H11E109.5
H11A—C11A—H11B109.5H11D—C11B—H11E109.5
C4A'—C11A—H11C109.5C4B'—C11B—H11F109.5
H11A—C11A—H11C109.5H11D—C11B—H11F109.5
H11B—C11A—H11C109.5H11E—C11B—H11F109.5
C6A'—C1A'—C2A'—C3A'0.4 (3)C6B'—C1B'—C2B'—C3B'2.1 (4)
C1A—C1A'—C2A'—C3A'177.7 (2)C1B—C1B'—C2B'—C3B'180.0 (2)
C1A'—C2A'—C3A'—C4A'0.4 (3)C1B'—C2B'—C3B'—C4B'0.3 (4)
C2A'—C3A'—C4A'—C5A'1.0 (4)C2B'—C3B'—C4B'—C5B'1.2 (4)
C2A'—C3A'—C4A'—C11A179.3 (2)C2B'—C3B'—C4B'—C11B178.3 (3)
C3A'—C4A'—C5A'—C6A'0.8 (4)C3B'—C4B'—C5B'—C6B'0.9 (4)
C11A—C4A'—C5A'—C6A'179.5 (2)C11B—C4B'—C5B'—C6B'178.5 (2)
C4A'—C5A'—C6A'—C1A'0.0 (4)C4B'—C5B'—C6B'—C1B'0.9 (4)
C2A'—C1A'—C6A'—C5A'0.6 (3)C2B'—C1B'—C6B'—C5B'2.3 (4)
C1A—C1A'—C6A'—C5A'178.0 (2)C1B—C1B'—C6B'—C5B'179.7 (2)
C2A'—C1A'—C1A—C6A136.7 (2)C6B'—C1B'—C1B—C6B42.9 (3)
C6A'—C1A'—C1A—C6A40.5 (3)C2B'—C1B'—C1B—C6B135.0 (2)
C2A'—C1A'—C1A—C2A43.0 (3)C6B'—C1B'—C1B—C2B136.9 (2)
C6A'—C1A'—C1A—C2A139.8 (2)C2B'—C1B'—C1B—C2B45.2 (3)
C6A—C1A—C2A—C3A1.2 (3)C6B—C1B—C2B—C3B3.4 (3)
C1A'—C1A—C2A—C3A179.1 (2)C1B'—C1B—C2B—C3B176.8 (2)
C6A—C1A—C2A—C7A177.0 (2)C6B—C1B—C2B—C7B173.7 (2)
C1A'—C1A—C2A—C7A3.2 (4)C1B'—C1B—C2B—C7B6.1 (3)
C1A—C2A—C3A—N1A179.8 (2)C1B—C2B—C3B—C4B0.2 (3)
C7A—C2A—C3A—N1A3.7 (3)C7B—C2B—C3B—C4B177.1 (2)
C1A—C2A—C3A—C4A1.8 (3)C1B—C2B—C3B—N1B178.3 (2)
C7A—C2A—C3A—C4A177.9 (2)C7B—C2B—C3B—N1B4.4 (3)
N1A—C3A—C4A—C5A179.5 (2)N1B—C3B—C4B—C5B179.1 (2)
C2A—C3A—C4A—C5A1.1 (4)C2B—C3B—C4B—C5B2.5 (3)
N1A—C3A—C4A—C8A1.3 (4)N1B—C3B—C4B—C8B2.8 (3)
C2A—C3A—C4A—C8A179.7 (2)C2B—C3B—C4B—C8B175.7 (2)
C3A—C4A—C5A—C6A0.1 (4)C3B—C4B—C5B—C6B1.8 (3)
C8A—C4A—C5A—C6A179.0 (2)C8B—C4B—C5B—C6B176.4 (2)
C3A—C4A—C5A—C9A178.5 (3)C3B—C4B—C5B—C9B178.5 (2)
C8A—C4A—C5A—C9A2.4 (4)C8B—C4B—C5B—C9B3.3 (3)
C4A—C5A—C6A—C1A0.8 (4)C2B—C1B—C6B—C5B4.2 (3)
C9A—C5A—C6A—C1A177.8 (3)C1B'—C1B—C6B—C5B176.0 (2)
C2A—C1A—C6A—C5A0.1 (4)C4B—C5B—C6B—C1B1.7 (3)
C1A'—C1A—C6A—C5A179.6 (2)C9B—C5B—C6B—C1B178.0 (2)
C1A—C2A—C7A—N2A173 (3)C1B—C2B—C7B—N2B166 (3)
C3A—C2A—C7A—N2A3 (3)C3B—C2B—C7B—N2B12 (3)
C3A—C4A—C8A—N3A46 (17)C3B—C4B—C8B—N3B28 (12)
C5A—C4A—C8A—N3A135 (17)C5B—C4B—C8B—N3B150 (12)
C6A—C5A—C9A—C10A33.2 (6)C4B—C5B—C9B—C10B83.7 (3)
C4A—C5A—C9A—C10A148.2 (4)C6B—C5B—C9B—C10B96.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1B—H1B1···N3A0.862.373.166 (3)154
N1A—H1A1···N3Ai0.862.523.228 (3)140
N1A—H1A2···N1Bi0.862.583.157 (3)126
Symmetry code: (i) x, y+1, z+1.
(II) 3-amino-2,4 dicyano-5-ethyl-4'- N,N diethyl amino Biphenyl top
Crystal data top
C20H22N4F(000) = 680
Mr = 318.42Dx = 1.156 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.8918 (2) ÅCell parameters from 5488 reflections
b = 10.3458 (2) Åθ = 1.8–28.6°
c = 16.5707 (2) ŵ = 0.07 mm1
β = 101.496 (1)°T = 293 K
V = 1829.80 (5) Å3Rectangular, pale yellow
Z = 40.40 × 0.26 × 0.14 mm
Data collection top
Siemens SMART CCD area detector
diffractometer
4478 independent reflections
Radiation source: fine-focus sealed tube2122 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
Detector resolution: 8.33 pixels mm-1θmax = 28.4°, θmin = 1.9°
ω scansh = 1412
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 713
Tmin = 0.972, Tmax = 0.990l = 2122
12556 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)] = 0.061H-atom parameters constrained
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.043P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4478 reflectionsΔρmax = 0.23 e Å3
221 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0115 (15)
Crystal data top
C20H22N4V = 1829.80 (5) Å3
Mr = 318.42Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.8918 (2) ŵ = 0.07 mm1
b = 10.3458 (2) ÅT = 293 K
c = 16.5707 (2) Å0.40 × 0.26 × 0.14 mm
β = 101.496 (1)°
Data collection top
Siemens SMART CCD area detector
diffractometer
4478 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
2122 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.990Rint = 0.079
12556 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 1.00Δρmax = 0.23 e Å3
4478 reflectionsΔρmin = 0.23 e Å3
221 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.96593 (15)0.08450 (16)0.20255 (10)0.0481 (5)
H1A1.00430.15050.22720.058*
H1B0.96030.01450.22960.058*
N20.86240 (19)0.22716 (19)0.16255 (12)0.0619 (6)
N31.02809 (18)0.40045 (18)0.15633 (11)0.0540 (5)
N40.51316 (17)0.41009 (19)0.19047 (11)0.0582 (5)
C1'0.72722 (17)0.11851 (19)0.05016 (11)0.0370 (5)
C2'0.63425 (19)0.1841 (2)0.02130 (12)0.0489 (6)
H2'0.61930.16370.03050.059*
C3'0.5630 (2)0.2786 (2)0.06669 (13)0.0498 (6)
H3'0.50030.31930.04530.060*
C4'0.58311 (18)0.3149 (2)0.14436 (12)0.0414 (5)
C5'0.67786 (17)0.25020 (19)0.17304 (11)0.0384 (5)
H5'0.69550.27270.22390.046*
C6'0.74603 (17)0.15358 (19)0.12764 (12)0.0373 (5)
H6'0.80670.11040.14960.045*
C10.79815 (17)0.00936 (19)0.00555 (11)0.0380 (5)
C20.85218 (17)0.01611 (18)0.07884 (11)0.0352 (5)
C30.91466 (17)0.09071 (18)0.12149 (11)0.0334 (5)
C40.92264 (17)0.20465 (18)0.07565 (11)0.0342 (5)
C50.87361 (18)0.2107 (2)0.00893 (12)0.0394 (5)
C60.81276 (19)0.1047 (2)0.04730 (12)0.0445 (5)
H60.77990.10920.10350.053*
C70.85451 (19)0.1355 (2)0.12362 (12)0.0418 (5)
C80.98159 (18)0.3146 (2)0.11921 (12)0.0391 (5)
C90.8801 (2)0.3355 (2)0.05525 (13)0.0503 (6)
H9A0.87400.31620.11320.060*
H9B0.96070.37600.03520.060*
C100.5292 (2)0.4405 (3)0.27370 (15)0.0678 (8)
H10A0.54970.36180.30000.081*
H10B0.45050.47290.30530.081*
C110.6291 (3)0.5381 (3)0.27568 (18)0.0918 (10)
H11A0.70730.50700.24440.138*
H11B0.63710.55250.33160.138*
H11C0.60740.61780.25230.138*
C120.4215 (2)0.4881 (3)0.15801 (16)0.0769 (9)
H12A0.44870.49690.09890.092*
H12B0.41800.57400.18190.092*
C130.2958 (3)0.4305 (3)0.17613 (19)0.1041 (11)
H13A0.29830.34670.15090.156*
H13B0.23860.48500.15470.156*
H13C0.26840.42190.23460.156*
C140.7786 (3)0.4282 (3)0.04611 (19)0.0931 (10)
H14A0.69850.39090.06920.140*
H14B0.78900.50710.07450.140*
H14C0.78290.44620.01120.140*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0723 (12)0.0351 (10)0.0300 (9)0.0146 (9)0.0060 (8)0.0034 (7)
N20.0935 (15)0.0351 (12)0.0516 (12)0.0044 (11)0.0009 (10)0.0074 (10)
N30.0763 (13)0.0345 (11)0.0491 (12)0.0095 (10)0.0073 (10)0.0062 (9)
N40.0584 (11)0.0613 (13)0.0565 (13)0.0270 (11)0.0155 (10)0.0232 (10)
C1'0.0418 (11)0.0341 (12)0.0323 (11)0.0041 (10)0.0010 (9)0.0014 (9)
C2'0.0587 (13)0.0536 (15)0.0345 (12)0.0125 (12)0.0099 (10)0.0083 (10)
C3'0.0534 (12)0.0523 (15)0.0451 (13)0.0203 (12)0.0131 (10)0.0064 (11)
C4'0.0401 (11)0.0383 (13)0.0442 (13)0.0047 (10)0.0046 (10)0.0056 (10)
C5'0.0424 (11)0.0361 (13)0.0352 (11)0.0024 (10)0.0044 (9)0.0032 (9)
C6'0.0378 (10)0.0330 (12)0.0404 (12)0.0017 (9)0.0056 (9)0.0035 (9)
C10.0442 (11)0.0313 (12)0.0360 (12)0.0044 (10)0.0020 (9)0.0010 (9)
C20.0429 (10)0.0263 (11)0.0352 (11)0.0015 (9)0.0053 (9)0.0023 (9)
C30.0378 (10)0.0280 (11)0.0331 (11)0.0015 (9)0.0038 (8)0.0002 (9)
C40.0419 (11)0.0253 (11)0.0342 (11)0.0044 (9)0.0046 (9)0.0005 (8)
C50.0460 (11)0.0330 (12)0.0373 (12)0.0009 (10)0.0037 (9)0.0020 (9)
C60.0597 (13)0.0378 (13)0.0314 (11)0.0057 (11)0.0022 (10)0.0033 (9)
C70.0540 (13)0.0322 (13)0.0359 (12)0.0021 (11)0.0012 (10)0.0023 (10)
C80.0473 (12)0.0308 (12)0.0380 (12)0.0002 (10)0.0058 (9)0.0044 (10)
C90.0713 (15)0.0351 (13)0.0418 (13)0.0010 (12)0.0043 (11)0.0104 (10)
C100.0685 (16)0.073 (2)0.0603 (17)0.0258 (15)0.0092 (13)0.0262 (14)
C110.097 (2)0.078 (2)0.108 (2)0.0193 (19)0.0389 (19)0.0321 (18)
C120.0730 (18)0.079 (2)0.081 (2)0.0307 (16)0.0205 (15)0.0359 (15)
C130.082 (2)0.138 (3)0.096 (2)0.018 (2)0.0248 (18)0.035 (2)
C140.112 (2)0.065 (2)0.106 (2)0.0348 (19)0.0313 (19)0.0401 (17)
Geometric parameters (Å, º) top
N1—C31.349 (2)C4—C51.398 (2)
N1—H1A0.8600C4—C81.429 (3)
N1—H1B0.8600C5—C61.370 (3)
N2—C71.141 (2)C5—C91.511 (3)
N3—C81.140 (2)C6—H60.9300
N4—C4'1.379 (2)C9—C141.494 (3)
N4—C121.467 (3)C9—H9A0.9700
N4—C101.459 (3)C9—H9B0.9700
C1'—C6'1.388 (3)C10—C111.490 (4)
C1'—C2'1.381 (3)C10—H10A0.9700
C1'—C11.480 (3)C10—H10B0.9700
C2'—C3'1.375 (3)C11—H11A0.9600
C2'—H2'0.9300C11—H11B0.9600
C3'—C4'1.399 (3)C11—H11C0.9600
C3'—H3'0.9300C12—C131.469 (4)
C4'—C5'1.391 (3)C12—H12A0.9700
C5'—C6'1.376 (3)C12—H12B0.9700
C5'—H5'0.9300C13—H13A0.9600
C6'—H6'0.9300C13—H13B0.9600
C1—C61.393 (3)C13—H13C0.9600
C1—C21.407 (2)C14—H14A0.9600
C2—C31.412 (3)C14—H14B0.9600
C2—C71.438 (3)C14—H14C0.9600
C3—C41.414 (2)
C3—N1—H1A120.0C5—C6—H6118.7
C3—N1—H1B120.0C1—C6—H6118.7
H1A—N1—H1B120.0N2—C7—C2175.8 (2)
C4'—N4—C12122.08 (18)N3—C8—C4177.7 (2)
C4'—N4—C10121.39 (18)C5—C9—C14112.74 (19)
C12—N4—C10116.51 (18)C5—C9—H9A109.0
C6'—C1'—C2'116.45 (18)C14—C9—H9A109.0
C6'—C1'—C1120.19 (18)C5—C9—H9B109.0
C2'—C1'—C1123.20 (18)C14—C9—H9B109.0
C3'—C2'—C1'122.2 (2)H9A—C9—H9B107.8
C3'—C2'—H2'118.9N4—C10—C11113.1 (2)
C1'—C2'—H2'118.9N4—C10—H10A109.0
C2'—C3'—C4'121.3 (2)C11—C10—H10A109.0
C2'—C3'—H3'119.4N4—C10—H10B109.0
C4'—C3'—H3'119.4C11—C10—H10B109.0
N4—C4'—C5'121.32 (18)H10A—C10—H10B107.8
N4—C4'—C3'122.05 (19)C10—C11—H11A109.5
C5'—C4'—C3'116.63 (18)C10—C11—H11B109.5
C4'—C5'—C6'121.26 (18)H11A—C11—H11B109.5
C4'—C5'—H5'119.4C10—C11—H11C109.5
C6'—C5'—H5'119.4H11A—C11—H11C109.5
C1'—C6'—C5'122.17 (18)H11B—C11—H11C109.5
C1'—C6'—H6'118.9N4—C12—C13112.1 (3)
C5'—C6'—H6'118.9N4—C12—H12A109.2
C6—C1—C2117.98 (17)C13—C12—H12A109.2
C6—C1—C1'119.89 (17)N4—C12—H12B109.2
C2—C1—C1'122.13 (17)C13—C12—H12B109.2
C1—C2—C3121.56 (17)H12A—C12—H12B107.9
C1—C2—C7121.10 (17)C12—C13—H13A109.5
C3—C2—C7117.17 (17)C12—C13—H13B109.5
N1—C3—C4121.11 (17)H13A—C13—H13B109.5
N1—C3—C2121.58 (17)C12—C13—H13C109.5
C4—C3—C2117.30 (17)H13A—C13—H13C109.5
C5—C4—C3121.57 (17)H13B—C13—H13C109.5
C5—C4—C8120.94 (18)C9—C14—H14A109.5
C3—C4—C8117.48 (17)C9—C14—H14B109.5
C6—C5—C4118.82 (18)H14A—C14—H14B109.5
C6—C5—C9121.02 (18)C9—C14—H14C109.5
C4—C5—C9120.01 (18)H14A—C14—H14C109.5
C5—C6—C1122.68 (18)H14B—C14—H14C109.5
C6'—C1'—C2'—C3'0.4 (3)C1—C2—C3—C41.0 (3)
C1—C1'—C2'—C3'174.9 (2)C7—C2—C3—C4174.24 (17)
C1'—C2'—C3'—C4'1.2 (3)N1—C3—C4—C5177.77 (17)
C12—N4—C4'—C5'173.8 (2)C2—C3—C4—C51.6 (3)
C10—N4—C4'—C5'4.6 (3)N1—C3—C4—C83.0 (3)
C12—N4—C4'—C3'6.0 (3)C2—C3—C4—C8177.67 (17)
C10—N4—C4'—C3'175.6 (2)C3—C4—C5—C62.3 (3)
C2'—C3'—C4'—N4179.5 (2)C8—C4—C5—C6176.98 (18)
C2'—C3'—C4'—C5'0.3 (3)C3—C4—C5—C9177.95 (18)
N4—C4'—C5'—C6'178.78 (19)C8—C4—C5—C91.3 (3)
C3'—C4'—C5'—C6'1.4 (3)C4—C5—C6—C10.3 (3)
C2'—C1'—C6'—C5'1.3 (3)C9—C5—C6—C1175.95 (19)
C1—C1'—C6'—C5'176.76 (17)C2—C1—C6—C52.2 (3)
C4'—C5'—C6'—C1'2.2 (3)C1'—C1—C6—C5177.71 (19)
C6'—C1'—C1—C643.8 (3)C1—C2—C7—N2157 (3)
C2'—C1'—C1—C6131.4 (2)C3—C2—C7—N218 (3)
C6'—C1'—C1—C2136.3 (2)C5—C4—C8—N3161 (5)
C2'—C1'—C1—C248.5 (3)C3—C4—C8—N318 (6)
C6—C1—C2—C32.8 (3)C6—C5—C9—C1494.5 (3)
C1'—C1—C2—C3177.06 (18)C4—C5—C9—C1481.1 (3)
C6—C1—C2—C7172.22 (19)C4'—N4—C10—C1187.6 (3)
C1'—C1—C2—C77.9 (3)C12—N4—C10—C1190.9 (3)
C1—C2—C3—N1179.64 (18)C4'—N4—C12—C1390.9 (3)
C7—C2—C3—N15.1 (3)C10—N4—C12—C1390.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.453.259 (2)158
N1—H1B···N3ii0.862.213.006 (2)154
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x+2, y1/2, z+1/2.

Experimental details

(I)(II)
Crystal data
Chemical formulaC17H15N3C20H22N4
Mr261.32318.42
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)293293
a, b, c (Å)7.8579 (1), 23.7627 (5), 15.3423 (2)10.8918 (2), 10.3458 (2), 16.5707 (2)
β (°) 94.765 (1) 101.496 (1)
V3)2854.89 (8)1829.80 (5)
Z84
Radiation typeMo KαMo Kα
µ (mm1)0.070.07
Crystal size (mm)0.30 × 0.24 × 0.140.40 × 0.26 × 0.14
Data collection
DiffractometerSiemens SMART CCD area detector
diffractometer
Siemens SMART CCD area detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.978, 0.9900.972, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
19861, 6961, 3077 12556, 4478, 2122
Rint0.0900.079
(sin θ/λ)max1)0.6670.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.173, 0.97 0.061, 0.145, 1.00
No. of reflections69614478
No. of parameters365221
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.300.23, 0.23

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) for (I) top
N1A—C3A1.360 (3)N1B—C3B1.363 (3)
N2A—C7A1.146 (3)N2B—C7B1.140 (3)
N3A—C8A1.141 (3)N3B—C8B1.143 (3)
C1A'—C1A1.485 (3)C1B'—C1B1.484 (3)
N2A—C7A—C2A174.7 (2)N2B—C7B—C2B174.8 (3)
N3A—C8A—C4A179.0 (3)N3B—C8B—C4B178.6 (3)
C2A'—C1A'—C1A—C6A136.7 (2)C6B'—C1B'—C1B—C6B42.9 (3)
C6A'—C1A'—C1A—C6A40.5 (3)C2B'—C1B'—C1B—C6B135.0 (2)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1B—H1B1···N3A0.862.373.166 (3)154
N1A—H1A1···N3Ai0.862.523.228 (3)140
N1A—H1A2···N1Bi0.862.583.157 (3)126
Symmetry code: (i) x, y+1, z+1.
Selected geometric parameters (Å, º) for (II) top
N1—C31.349 (2)N4—C121.467 (3)
N2—C71.141 (2)N4—C101.459 (3)
N3—C81.140 (2)C1'—C11.480 (3)
N4—C4'1.379 (2)
C4'—N4—C12122.08 (18)N2—C7—C2175.8 (2)
C4'—N4—C10121.39 (18)N3—C8—C4177.7 (2)
C12—N4—C10116.51 (18)
C6'—C1'—C1—C643.8 (3)C2'—C1'—C1—C6131.4 (2)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.453.259 (2)158
N1—H1B···N3ii0.862.213.006 (2)154
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x+2, y1/2, z+1/2.
 

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