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The crystal structure of the title compound, C9H11NO·C9H9N5, contains one mol­ecule of each component in the asymmetric unit. Approximately planar clusters of four mol­ecules are formed by N-H...N and N-H...O hydrogen bonds, and further N-H...N hydrogen bonds link adjacent clusters to form pleated ribbons. [pi]-[pi] inter­actions are found between triazine and aldehyde benzene rings in different clusters, generating stacks along the monoclinic b axis. The intra­molecular geometry of the two components is similar to that found in other crystal structures containing these mol­ecules. Both mol­ecules are approximately planar, except for methyl H atoms, with a small twist about the C-C bond linking the phenyl and triazine rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107031307/sf3045sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107031307/sf3045Isup2.hkl
Contains datablock I

CCDC reference: 639248

Comment top

Hydrogen bonding plays a key role in chemical, catalytic and biochemical processes, as well as in supramolecular chemistry and crystal engineering (Epstein & Shubina, 2002). Heterocycles are very important in studies of new pharmaceuticals and agrochemicals. In recent years, many new chemicals have been synthesized that have structures containing heterocyclic rings, such as triazine (Chen et al., 2001). Triazine derivatives have demonstrated a broad range of biological activities, including anti-angiogenesis, herbicidal effects, antimetastatic effects, Erm methyltransferase inhibition, antimicrobial effects (Bork et al., 2003), the inhibition of the differentiation of endothelial progenitor cells (Park et al., 2003) and the prevention of the early cell death of transplanted myogenic cells (El Fahime et al., 2003). The crystal structure of the title compound, (I), consists of 4-dimethylaminobenzaldehyde and 6-phenyl-1,3,5-triazine-2,4-diamine molecules, with one of each in the asymmetric unit (Fig. 1).

Although the unit-cell parameters have been reported for 4-dimethylaminobenzaldehyde (Reffner & McCrone, 1959), there is no report of the crystal structure of this compound. The structure of its hydrobromide is known (Dattagupta & Saha, 1973), as are those of a 1:1 complex in which it acts as a guest molecule in channels (Herbstein et al., 1984), and of a tin complex in which it serves as a ligand coordinating through its O atom (Mahadevan et al., 1982). In each case, the aldehyde group is essentially coplanar with the benzene ring, and the same is true of the dimethylamino group when it remains unprotonated. Relevant torsion angles for the title cocrystal are given in Table 1.

The crystal structure of 6-phenyl-1,3,5-triazine-2,4-diamine has been reported (Diaz-Ortiz et al., 2004), as have a number of cocrystals (Deak, Radics et al., 2001; Bertolasi et al., 2001; Bishop et al., 2002), salts (Wijaya et al., 2004; Adachi et al., 2005; Sheshmani et al., 2006; Aghabozorg et al., 2006) and a metal complex in which is serves as a ligand (Deák, Kálmán et al., 2001). In most cases, the two rings are approximately coplanar, usually with a small twist around the bond linking them, as is found in the title cocrystal, but torsion angles range up to 33°.

Based on their work on s-triazine derivatives, Główka & Iwanicka (1989a,b) concluded that the endocyclic bond angles at all N atoms are less than 120°, while those at the C atoms are larger than 120°, irrespective of their hybridization. The 1,3,5-triazine ring in the title cocrystal has the same characteristics: the endocyclic bond angles at the N atoms lie in the range 124.7 (1)–126.6 (1)° and those at the C atoms lie in the range 113.9 (1)–114.9 (1)°. The values of the N—C bond lengths within the 1,3,5-triazine ring (Table 1) are comparable with those found in crystal structures of other N-heteroaromatic derivatives (Allen et al., 1987; Chen et al., 2001). Triazine itself, (HCN)3, has a C—N bond distance in the same range at low temperature [1.338 (4) Å; Smith & Rae, 1978], though it appears to be shorter at room temperature (Wheatley, 1955; Coppens, 1967), probably because of libration effects. The exocyclic C—N bond distances for the 1,3,5-triazine ring [1.3323 (17)–1.3598 (16) Å] are significantly larger than those in other similar triazine molecules (1.325–1.333 Å). The narrow CNC angles (ca 113°) and the wide NCN angles (ca 126°) in the present compound are very similar to the CNC [114.8 (10)°] and NCN [125.2 (10)°] angles of (HCN)3. The two amine groups lie essentially in the triazine ring plane (Table 2). The dihedral angle between the connected phenyl and triazine rings is 13.8 (1)°.

The supramolecular structure of the title cocrystal involves hydrogen bonding (Table 2) and ππ stacking. The hydrogen-bond donors are the four N—H bonds of the two amino groups, while the acceptors are the aldehyde O atom and two of the three triazine ring N atoms; the third ring N atom and the dimethylamino N atom do not take part in hydrogen bonding. Pairs of triazine molecules form centrosymmetric dimers via N—H···N hydrogen bonds, and two aldehyde molecules are linked to this dimer by two N—H···O hydrogen bonds each, to give an approximately planar cluster of four molecules with six hydrogen bonds (Fig. 2). Each such cluster is linked to two other clusters, one on each side, by pairs of N—H···N hydrogen bonds arranged around twofold rotation axes, with adjacent clusters inclined to each other by approximately 40°; these links are also shown in Fig. 2. The complete hydrogen bonding thus forms pleated ribbons along the c axis (Fig. 3).

The benzene rings of the aldehyde and triazine rings of (I) are stacked via ππ interactions along the b axis, having a centroid-to-centroid distance of 3.432 Å and a perpendicular interplanar distance of 3.341 Å, as shown in Fig. 4.

Related literature top

For related literature, see: Adachi et al. (2005); Aghabozorg et al. (2006); Allen et al. (1987); Bertolasi et al. (2001); Bishop et al. (2002); Bork et al. (2003); Chen et al. (2001); Coppens (1967); Dattagupta & Saha (1973); Deák et al. (2001); Deak et al. (2001); Diaz-Ortiz, Elguero, Foces-Foces, de la Hoz, Moreno, del Carmen Mateo, Sanchez-Migallon & Valiente (2004); El Fahime, Bouchentouf, Benabdallah, Skuk, Lafreniere, Chang & Tremblay (2003); Epstein & Shubina (2002); Główka & Iwanicka (1989a, 1989b); Herbstein et al. (1984); Mahadevan et al. (1982); Park et al. (2003); Reffner & McCrone (1959); Sheshmani et al. (2006); Smith & Rae (1978); Wheatley (1955); Wijaya et al. (2004).

Experimental top

The title compound, (I), was prepared by dissolving 4-dimethylaminobenzaldehyde (1 mmol, 149 mg) and 6-phenyl-1,3,5-triazine-2,4-diamine (1 mmol, 18 7 mg) in chloroform (10 ml). The mixture was stirred at room temperature for 4 h. The solid product was filtered off and recrystallized from ethanol and dichloromethane (1:1), affording small colourless crystals.

Refinement top

Amino H atoms were found in a difference map and refined freely. Other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.95–0.98 Å, and with Uiso(H) = 1.2Ueq(Csp2) or 1.5Ueq(Csp3).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2005); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The hydrogen bonding (dashed lines) connecting two molecules of each component of (I) into an approximately planar centrosymmetric unit and linking each of these units to two adjacent units.
[Figure 3] Fig. 3. The formation of pleated sheets of molecules of (I) by hydrogen bonding.
[Figure 4] Fig. 4. The stacking of molecules of (I) via ππ interactions.
4-(dimethylamino)benzaldehyde–6-phenyl-1,3,5-triazine-2,4-diamine (1/1) top
Crystal data top
C9H11NO·C9H9N5F(000) = 1424
Mr = 336.40Dx = 1.314 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7006 reflections
a = 15.848 (3) Åθ = 2.2–28.3°
b = 10.689 (2) ŵ = 0.09 mm1
c = 20.078 (5) ÅT = 150 K
β = 91.380 (11)°Block, colourless
V = 3400.3 (13) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
3134 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.027
Graphite monochromatorθmax = 28.4°, θmin = 2.3°
thin–slice ω scansh = 2021
14907 measured reflectionsk = 1413
4131 independent reflectionsl = 2626
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)] = 0.045Hydrogen site location: mixed
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.061P)2 + 2.542P]
where P = (Fo2 + 2Fc2)/3
4131 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C9H11NO·C9H9N5V = 3400.3 (13) Å3
Mr = 336.40Z = 8
Monoclinic, C2/cMo Kα radiation
a = 15.848 (3) ŵ = 0.09 mm1
b = 10.689 (2) ÅT = 150 K
c = 20.078 (5) Å0.30 × 0.20 × 0.20 mm
β = 91.380 (11)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
3134 reflections with I > 2σ(I)
14907 measured reflectionsRint = 0.027
4131 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.35 e Å3
4131 reflectionsΔρmin = 0.23 e Å3
244 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.22112 (6)1.01494 (11)0.62533 (5)0.0321 (3)
N10.58181 (8)0.81714 (13)0.53056 (7)0.0305 (3)
N20.05155 (7)0.91075 (13)0.32460 (6)0.0259 (3)
H2A0.0590 (10)0.8873 (15)0.2817 (9)0.025 (4)*
H2B0.0935 (12)0.9401 (17)0.3456 (9)0.033 (5)*
N30.03216 (7)0.94699 (11)0.41732 (5)0.0217 (3)
N40.11979 (8)0.97534 (14)0.50757 (6)0.0297 (3)
H4A0.1717 (12)0.9700 (17)0.5285 (9)0.038 (5)*
H4B0.0744 (12)1.0002 (17)0.5293 (9)0.034 (5)*
N50.08944 (7)0.86173 (11)0.31803 (5)0.0194 (2)
N60.18025 (7)0.90134 (11)0.41205 (5)0.0209 (2)
C10.29085 (9)1.00545 (13)0.65223 (7)0.0250 (3)
H1A0.29701.03350.69700.030*
C20.36493 (8)0.95468 (13)0.62102 (7)0.0221 (3)
C30.44327 (9)0.95690 (14)0.65480 (7)0.0253 (3)
H3A0.44680.98940.69880.030*
C40.51537 (9)0.91306 (14)0.62568 (7)0.0274 (3)
H4C0.56780.91670.64960.033*
C50.51203 (8)0.86276 (13)0.56058 (7)0.0242 (3)
C60.43225 (9)0.85998 (14)0.52696 (7)0.0251 (3)
H6A0.42800.82660.48310.030*
C70.36130 (9)0.90454 (13)0.55656 (7)0.0243 (3)
H7A0.30870.90140.53290.029*
C80.66400 (10)0.82048 (19)0.56375 (9)0.0418 (4)
H8A0.66050.78120.60770.063*
H8B0.68230.90760.56900.063*
H8C0.70480.77490.53700.063*
C90.57584 (10)0.77145 (16)0.46248 (8)0.0336 (4)
H9A0.53720.69990.46020.050*
H9B0.63180.74540.44810.050*
H9C0.55440.83820.43320.050*
C100.31944 (9)0.82286 (16)0.33911 (8)0.0297 (3)
H100.32920.86920.37890.036*
C110.38712 (9)0.76977 (17)0.30653 (8)0.0364 (4)
H110.44290.78100.32390.044*
C120.37355 (9)0.70074 (15)0.24897 (8)0.0320 (3)
H120.41990.66360.22720.038*
C130.29249 (9)0.68592 (14)0.22316 (7)0.0272 (3)
H130.28310.63870.18360.033*
C140.22434 (8)0.74019 (13)0.25514 (7)0.0229 (3)
H140.16880.73050.23700.028*
C150.23732 (8)0.80845 (13)0.31358 (6)0.0205 (3)
C160.16428 (8)0.86146 (12)0.35016 (6)0.0188 (3)
C170.02476 (8)0.90696 (12)0.35424 (6)0.0190 (3)
C180.11070 (8)0.94050 (13)0.44426 (6)0.0210 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0213 (5)0.0449 (7)0.0300 (6)0.0090 (5)0.0023 (4)0.0047 (5)
N10.0194 (6)0.0367 (7)0.0356 (7)0.0044 (5)0.0024 (5)0.0018 (6)
N20.0158 (6)0.0428 (8)0.0189 (6)0.0065 (5)0.0006 (4)0.0063 (5)
N30.0181 (5)0.0272 (6)0.0196 (6)0.0039 (4)0.0010 (4)0.0027 (4)
N40.0199 (6)0.0478 (8)0.0213 (6)0.0088 (5)0.0034 (5)0.0091 (5)
N50.0169 (5)0.0238 (6)0.0175 (5)0.0012 (4)0.0012 (4)0.0006 (4)
N60.0166 (5)0.0258 (6)0.0204 (5)0.0013 (4)0.0008 (4)0.0016 (4)
C10.0246 (7)0.0252 (7)0.0251 (7)0.0022 (6)0.0010 (5)0.0002 (5)
C20.0192 (6)0.0215 (7)0.0257 (7)0.0006 (5)0.0003 (5)0.0034 (5)
C30.0236 (7)0.0278 (7)0.0242 (7)0.0001 (6)0.0024 (5)0.0011 (6)
C40.0189 (6)0.0319 (8)0.0313 (8)0.0007 (6)0.0051 (5)0.0045 (6)
C50.0191 (6)0.0232 (7)0.0303 (7)0.0013 (5)0.0022 (5)0.0055 (6)
C60.0234 (7)0.0266 (7)0.0254 (7)0.0012 (5)0.0003 (5)0.0004 (6)
C70.0187 (6)0.0262 (7)0.0278 (7)0.0015 (5)0.0032 (5)0.0023 (6)
C80.0194 (7)0.0586 (11)0.0475 (10)0.0077 (7)0.0012 (7)0.0045 (8)
C90.0287 (8)0.0367 (9)0.0358 (8)0.0042 (6)0.0084 (6)0.0010 (7)
C100.0205 (7)0.0395 (9)0.0290 (7)0.0012 (6)0.0004 (6)0.0075 (6)
C110.0169 (7)0.0507 (10)0.0416 (9)0.0041 (7)0.0000 (6)0.0089 (8)
C120.0225 (7)0.0381 (9)0.0358 (8)0.0068 (6)0.0084 (6)0.0018 (7)
C130.0272 (7)0.0303 (8)0.0243 (7)0.0033 (6)0.0043 (6)0.0025 (6)
C140.0189 (6)0.0265 (7)0.0233 (7)0.0015 (5)0.0000 (5)0.0009 (5)
C150.0179 (6)0.0222 (7)0.0215 (6)0.0008 (5)0.0018 (5)0.0017 (5)
C160.0177 (6)0.0190 (6)0.0197 (6)0.0004 (5)0.0015 (5)0.0017 (5)
C170.0181 (6)0.0206 (6)0.0184 (6)0.0004 (5)0.0000 (5)0.0013 (5)
C180.0200 (6)0.0228 (7)0.0201 (6)0.0015 (5)0.0006 (5)0.0009 (5)
Geometric parameters (Å, º) top
O1—C11.2225 (17)C4—C51.413 (2)
N1—C51.3623 (18)C5—C61.4192 (19)
N1—C81.449 (2)C6—H6A0.950
N1—C91.453 (2)C6—C71.370 (2)
N2—H2A0.902 (17)C7—H7A0.950
N2—H2B0.855 (19)C8—H8A0.980
N2—C171.3355 (17)C8—H8B0.980
N3—C171.3392 (17)C8—H8C0.980
N3—C181.3469 (17)C9—H9A0.980
N4—H4A0.917 (19)C9—H9B0.980
N4—H4B0.89 (2)C9—H9C0.980
N4—C181.3292 (18)C10—H100.950
N5—C161.3363 (16)C10—C111.391 (2)
N5—C171.3598 (16)C10—C151.3958 (19)
N6—C161.3323 (17)C11—H110.950
N6—C181.3575 (17)C11—C121.384 (2)
C1—H1A0.950C12—H120.950
C1—C21.4494 (19)C12—C131.383 (2)
C2—C31.4005 (19)C13—H130.950
C2—C71.401 (2)C13—C141.3959 (19)
C3—H3A0.950C14—H140.950
C3—C41.378 (2)C14—C151.3927 (19)
C4—H4C0.950C15—C161.4972 (18)
C5—N1—C8121.20 (13)H8A—C8—H8B109.5
C5—N1—C9120.10 (12)H8A—C8—H8C109.5
C8—N1—C9118.58 (13)H8B—C8—H8C109.5
H2A—N2—H2B119.1 (16)N1—C9—H9A109.5
H2A—N2—C17120.9 (10)N1—C9—H9B109.5
H2B—N2—C17119.9 (12)N1—C9—H9C109.5
C17—N3—C18114.98 (11)H9A—C9—H9B109.5
H4A—N4—H4B121.4 (16)H9A—C9—H9C109.5
H4A—N4—C18119.8 (12)H9B—C9—H9C109.5
H4B—N4—C18118.8 (11)H10—C10—C11119.8
C16—N5—C17114.48 (11)H10—C10—C15119.8
C16—N6—C18113.87 (11)C11—C10—C15120.33 (14)
O1—C1—H1A117.5C10—C11—H11119.9
O1—C1—C2124.97 (13)C10—C11—C12120.29 (14)
H1A—C1—C2117.5H11—C11—C12119.9
C1—C2—C3120.14 (13)C11—C12—H12120.1
C1—C2—C7121.80 (12)C11—C12—C13119.89 (13)
C3—C2—C7118.05 (12)H12—C12—C13120.1
C2—C3—H3A119.2C12—C13—H13119.9
C2—C3—C4121.54 (13)C12—C13—C14120.14 (13)
H3A—C3—C4119.2H13—C13—C14119.9
C3—C4—H4C119.7C13—C14—H14119.8
C3—C4—C5120.59 (13)C13—C14—C15120.33 (12)
H4C—C4—C5119.7H14—C14—C15119.8
N1—C5—C4122.19 (13)C10—C15—C14118.99 (12)
N1—C5—C6120.36 (13)C10—C15—C16120.21 (12)
C4—C5—C6117.45 (12)C14—C15—C16120.75 (12)
C5—C6—H6A119.4N5—C16—N6126.59 (12)
C5—C6—C7121.17 (13)N5—C16—C15116.85 (11)
H6A—C6—C7119.4N6—C16—C15116.55 (11)
C2—C7—C6121.20 (13)N2—C17—N3118.00 (12)
C2—C7—H7A119.4N2—C17—N5117.31 (12)
C6—C7—H7A119.4N3—C17—N5124.69 (12)
N1—C8—H8A109.5N3—C18—N4116.58 (12)
N1—C8—H8B109.5N3—C18—N6125.29 (12)
N1—C8—H8C109.5N4—C18—N6118.13 (12)
O1—C1—C2—C3175.17 (14)C13—C14—C15—C100.7 (2)
O1—C1—C2—C73.6 (2)C13—C14—C15—C16176.84 (13)
C1—C2—C3—C4177.88 (13)C11—C10—C15—C140.0 (2)
C7—C2—C3—C41.0 (2)C11—C10—C15—C16177.62 (14)
C2—C3—C4—C50.8 (2)C18—N6—C16—N52.8 (2)
C8—N1—C5—C41.3 (2)C18—N6—C16—C15175.79 (11)
C8—N1—C5—C6179.27 (15)C17—N5—C16—N60.7 (2)
C9—N1—C5—C4177.29 (14)C17—N5—C16—C15177.90 (11)
C9—N1—C5—C63.3 (2)C10—C15—C16—N5169.71 (13)
C3—C4—C5—N1179.15 (14)C10—C15—C16—N611.58 (19)
C3—C4—C5—C60.2 (2)C14—C15—C16—N512.76 (19)
N1—C5—C6—C7179.48 (14)C14—C15—C16—N6165.95 (12)
C4—C5—C6—C70.1 (2)C18—N3—C17—N2179.91 (12)
C5—C6—C7—C20.1 (2)C18—N3—C17—N50.34 (19)
C1—C2—C7—C6178.18 (13)C16—N5—C17—N2179.37 (12)
C3—C2—C7—C60.6 (2)C16—N5—C17—N31.05 (19)
C15—C10—C11—C120.9 (3)C17—N3—C18—N4177.70 (13)
C10—C11—C12—C130.9 (3)C17—N3—C18—N62.2 (2)
C11—C12—C13—C140.2 (2)C16—N6—C18—N33.6 (2)
C12—C13—C14—C150.7 (2)C16—N6—C18—N4176.28 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N5i0.902 (17)2.066 (18)2.9585 (18)169.8 (15)
N2—H2B···O1ii0.855 (19)2.173 (19)2.9990 (16)162.4 (16)
N4—H4A···O10.917 (19)2.132 (19)2.8575 (17)135.2 (15)
N4—H4B···N3ii0.89 (2)2.10 (2)2.9895 (18)177.9 (17)
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC9H11NO·C9H9N5
Mr336.40
Crystal system, space groupMonoclinic, C2/c
Temperature (K)150
a, b, c (Å)15.848 (3), 10.689 (2), 20.078 (5)
β (°) 91.380 (11)
V3)3400.3 (13)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 1K CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
14907, 4131, 3134
Rint0.027
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.129, 1.05
No. of reflections4131
No. of parameters244
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.35, 0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Bruker, 2005), SHELXTL and local programs.

Selected geometric parameters (Å, º) top
N2—C171.3355 (17)N5—C161.3363 (16)
N3—C171.3392 (17)N5—C171.3598 (16)
N3—C181.3469 (17)N6—C161.3323 (17)
N4—C181.3292 (18)N6—C181.3575 (17)
C17—N3—C18114.98 (11)N5—C16—N6126.59 (12)
C16—N5—C17114.48 (11)N3—C17—N5124.69 (12)
C16—N6—C18113.87 (11)N3—C18—N6125.29 (12)
O1—C1—C2—C3175.17 (14)C9—N1—C5—C63.3 (2)
O1—C1—C2—C73.6 (2)C10—C15—C16—N5169.71 (13)
C8—N1—C5—C41.3 (2)C10—C15—C16—N611.58 (19)
C8—N1—C5—C6179.27 (15)C14—C15—C16—N512.76 (19)
C9—N1—C5—C4177.29 (14)C14—C15—C16—N6165.95 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N5i0.902 (17)2.066 (18)2.9585 (18)169.8 (15)
N2—H2B···O1ii0.855 (19)2.173 (19)2.9990 (16)162.4 (16)
N4—H4A···O10.917 (19)2.132 (19)2.8575 (17)135.2 (15)
N4—H4B···N3ii0.89 (2)2.10 (2)2.9895 (18)177.9 (17)
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+2, z+1.
 

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