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The crystal structure of the title compound, C
9H
11NO·C
9H
9N
5, 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.
-
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
CCDC reference: 639248
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.
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).
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.
4-(dimethylamino)benzaldehyde–6-phenyl-1,3,5-triazine-2,4-diamine (1/1)
top
Crystal data top
C9H11NO·C9H9N5 | F(000) = 1424 |
Mr = 336.40 | Dx = 1.314 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 7006 reflections |
a = 15.848 (3) Å | θ = 2.2–28.3° |
b = 10.689 (2) Å | µ = 0.09 mm−1 |
c = 20.078 (5) Å | T = 150 K |
β = 91.380 (11)° | Block, colourless |
V = 3400.3 (13) Å3 | 0.30 × 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 tube | Rint = 0.027 |
Graphite monochromator | θmax = 28.4°, θmin = 2.3° |
thin–slice ω scans | h = −20→21 |
14907 measured reflections | k = −14→13 |
4131 independent reflections | l = −26→26 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: mixed |
wR(F2) = 0.129 | H 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 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Crystal data top
C9H11NO·C9H9N5 | V = 3400.3 (13) Å3 |
Mr = 336.40 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 15.848 (3) Å | µ = 0.09 mm−1 |
b = 10.689 (2) Å | T = 150 K |
c = 20.078 (5) Å | 0.30 × 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 reflections | Rint = 0.027 |
4131 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.35 e Å−3 |
4131 reflections | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.22112 (6) | 1.01494 (11) | 0.62533 (5) | 0.0321 (3) | |
N1 | 0.58181 (8) | 0.81714 (13) | 0.53056 (7) | 0.0305 (3) | |
N2 | −0.05155 (7) | 0.91075 (13) | 0.32460 (6) | 0.0259 (3) | |
H2A | −0.0590 (10) | 0.8873 (15) | 0.2817 (9) | 0.025 (4)* | |
H2B | −0.0935 (12) | 0.9401 (17) | 0.3456 (9) | 0.033 (5)* | |
N3 | 0.03216 (7) | 0.94699 (11) | 0.41732 (5) | 0.0217 (3) | |
N4 | 0.11979 (8) | 0.97534 (14) | 0.50757 (6) | 0.0297 (3) | |
H4A | 0.1717 (12) | 0.9700 (17) | 0.5285 (9) | 0.038 (5)* | |
H4B | 0.0744 (12) | 1.0002 (17) | 0.5293 (9) | 0.034 (5)* | |
N5 | 0.08944 (7) | 0.86173 (11) | 0.31803 (5) | 0.0194 (2) | |
N6 | 0.18025 (7) | 0.90134 (11) | 0.41205 (5) | 0.0209 (2) | |
C1 | 0.29085 (9) | 1.00545 (13) | 0.65223 (7) | 0.0250 (3) | |
H1A | 0.2970 | 1.0335 | 0.6970 | 0.030* | |
C2 | 0.36493 (8) | 0.95468 (13) | 0.62102 (7) | 0.0221 (3) | |
C3 | 0.44327 (9) | 0.95690 (14) | 0.65480 (7) | 0.0253 (3) | |
H3A | 0.4468 | 0.9894 | 0.6988 | 0.030* | |
C4 | 0.51537 (9) | 0.91306 (14) | 0.62568 (7) | 0.0274 (3) | |
H4C | 0.5678 | 0.9167 | 0.6496 | 0.033* | |
C5 | 0.51203 (8) | 0.86276 (13) | 0.56058 (7) | 0.0242 (3) | |
C6 | 0.43225 (9) | 0.85998 (14) | 0.52696 (7) | 0.0251 (3) | |
H6A | 0.4280 | 0.8266 | 0.4831 | 0.030* | |
C7 | 0.36130 (9) | 0.90454 (13) | 0.55656 (7) | 0.0243 (3) | |
H7A | 0.3087 | 0.9014 | 0.5329 | 0.029* | |
C8 | 0.66400 (10) | 0.82048 (19) | 0.56375 (9) | 0.0418 (4) | |
H8A | 0.6605 | 0.7812 | 0.6077 | 0.063* | |
H8B | 0.6823 | 0.9076 | 0.5690 | 0.063* | |
H8C | 0.7048 | 0.7749 | 0.5370 | 0.063* | |
C9 | 0.57584 (10) | 0.77145 (16) | 0.46248 (8) | 0.0336 (4) | |
H9A | 0.5372 | 0.6999 | 0.4602 | 0.050* | |
H9B | 0.6318 | 0.7454 | 0.4481 | 0.050* | |
H9C | 0.5544 | 0.8382 | 0.4332 | 0.050* | |
C10 | 0.31944 (9) | 0.82286 (16) | 0.33911 (8) | 0.0297 (3) | |
H10 | 0.3292 | 0.8692 | 0.3789 | 0.036* | |
C11 | 0.38712 (9) | 0.76977 (17) | 0.30653 (8) | 0.0364 (4) | |
H11 | 0.4429 | 0.7810 | 0.3239 | 0.044* | |
C12 | 0.37355 (9) | 0.70074 (15) | 0.24897 (8) | 0.0320 (3) | |
H12 | 0.4199 | 0.6636 | 0.2272 | 0.038* | |
C13 | 0.29249 (9) | 0.68592 (14) | 0.22316 (7) | 0.0272 (3) | |
H13 | 0.2831 | 0.6387 | 0.1836 | 0.033* | |
C14 | 0.22434 (8) | 0.74019 (13) | 0.25514 (7) | 0.0229 (3) | |
H14 | 0.1688 | 0.7305 | 0.2370 | 0.028* | |
C15 | 0.23732 (8) | 0.80845 (13) | 0.31358 (6) | 0.0205 (3) | |
C16 | 0.16428 (8) | 0.86146 (12) | 0.35016 (6) | 0.0188 (3) | |
C17 | 0.02476 (8) | 0.90696 (12) | 0.35424 (6) | 0.0190 (3) | |
C18 | 0.11070 (8) | 0.94050 (13) | 0.44426 (6) | 0.0210 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0213 (5) | 0.0449 (7) | 0.0300 (6) | 0.0090 (5) | −0.0023 (4) | −0.0047 (5) |
N1 | 0.0194 (6) | 0.0367 (7) | 0.0356 (7) | 0.0044 (5) | 0.0024 (5) | 0.0018 (6) |
N2 | 0.0158 (6) | 0.0428 (8) | 0.0189 (6) | 0.0065 (5) | −0.0006 (4) | −0.0063 (5) |
N3 | 0.0181 (5) | 0.0272 (6) | 0.0196 (6) | 0.0039 (4) | −0.0010 (4) | −0.0027 (4) |
N4 | 0.0199 (6) | 0.0478 (8) | 0.0213 (6) | 0.0088 (5) | −0.0034 (5) | −0.0091 (5) |
N5 | 0.0169 (5) | 0.0238 (6) | 0.0175 (5) | 0.0012 (4) | 0.0012 (4) | −0.0006 (4) |
N6 | 0.0166 (5) | 0.0258 (6) | 0.0204 (5) | 0.0013 (4) | −0.0008 (4) | −0.0016 (4) |
C1 | 0.0246 (7) | 0.0252 (7) | 0.0251 (7) | 0.0022 (6) | −0.0010 (5) | 0.0002 (5) |
C2 | 0.0192 (6) | 0.0215 (7) | 0.0257 (7) | 0.0006 (5) | −0.0003 (5) | 0.0034 (5) |
C3 | 0.0236 (7) | 0.0278 (7) | 0.0242 (7) | 0.0001 (6) | −0.0024 (5) | 0.0011 (6) |
C4 | 0.0189 (6) | 0.0319 (8) | 0.0313 (8) | −0.0007 (6) | −0.0051 (5) | 0.0045 (6) |
C5 | 0.0191 (6) | 0.0232 (7) | 0.0303 (7) | 0.0013 (5) | 0.0022 (5) | 0.0055 (6) |
C6 | 0.0234 (7) | 0.0266 (7) | 0.0254 (7) | 0.0012 (5) | −0.0003 (5) | 0.0004 (6) |
C7 | 0.0187 (6) | 0.0262 (7) | 0.0278 (7) | 0.0015 (5) | −0.0032 (5) | 0.0023 (6) |
C8 | 0.0194 (7) | 0.0586 (11) | 0.0475 (10) | 0.0077 (7) | 0.0012 (7) | −0.0045 (8) |
C9 | 0.0287 (8) | 0.0367 (9) | 0.0358 (8) | 0.0042 (6) | 0.0084 (6) | 0.0010 (7) |
C10 | 0.0205 (7) | 0.0395 (9) | 0.0290 (7) | 0.0012 (6) | −0.0004 (6) | −0.0075 (6) |
C11 | 0.0169 (7) | 0.0507 (10) | 0.0416 (9) | 0.0041 (7) | 0.0000 (6) | −0.0089 (8) |
C12 | 0.0225 (7) | 0.0381 (9) | 0.0358 (8) | 0.0068 (6) | 0.0084 (6) | −0.0018 (7) |
C13 | 0.0272 (7) | 0.0303 (8) | 0.0243 (7) | 0.0033 (6) | 0.0043 (6) | −0.0025 (6) |
C14 | 0.0189 (6) | 0.0265 (7) | 0.0233 (7) | 0.0015 (5) | 0.0000 (5) | 0.0009 (5) |
C15 | 0.0179 (6) | 0.0222 (7) | 0.0215 (6) | 0.0008 (5) | 0.0018 (5) | 0.0017 (5) |
C16 | 0.0177 (6) | 0.0190 (6) | 0.0197 (6) | −0.0004 (5) | 0.0015 (5) | 0.0017 (5) |
C17 | 0.0181 (6) | 0.0206 (6) | 0.0184 (6) | 0.0004 (5) | 0.0000 (5) | 0.0013 (5) |
C18 | 0.0200 (6) | 0.0228 (7) | 0.0201 (6) | 0.0015 (5) | −0.0006 (5) | −0.0009 (5) |
Geometric parameters (Å, º) top
O1—C1 | 1.2225 (17) | C4—C5 | 1.413 (2) |
N1—C5 | 1.3623 (18) | C5—C6 | 1.4192 (19) |
N1—C8 | 1.449 (2) | C6—H6A | 0.950 |
N1—C9 | 1.453 (2) | C6—C7 | 1.370 (2) |
N2—H2A | 0.902 (17) | C7—H7A | 0.950 |
N2—H2B | 0.855 (19) | C8—H8A | 0.980 |
N2—C17 | 1.3355 (17) | C8—H8B | 0.980 |
N3—C17 | 1.3392 (17) | C8—H8C | 0.980 |
N3—C18 | 1.3469 (17) | C9—H9A | 0.980 |
N4—H4A | 0.917 (19) | C9—H9B | 0.980 |
N4—H4B | 0.89 (2) | C9—H9C | 0.980 |
N4—C18 | 1.3292 (18) | C10—H10 | 0.950 |
N5—C16 | 1.3363 (16) | C10—C11 | 1.391 (2) |
N5—C17 | 1.3598 (16) | C10—C15 | 1.3958 (19) |
N6—C16 | 1.3323 (17) | C11—H11 | 0.950 |
N6—C18 | 1.3575 (17) | C11—C12 | 1.384 (2) |
C1—H1A | 0.950 | C12—H12 | 0.950 |
C1—C2 | 1.4494 (19) | C12—C13 | 1.383 (2) |
C2—C3 | 1.4005 (19) | C13—H13 | 0.950 |
C2—C7 | 1.401 (2) | C13—C14 | 1.3959 (19) |
C3—H3A | 0.950 | C14—H14 | 0.950 |
C3—C4 | 1.378 (2) | C14—C15 | 1.3927 (19) |
C4—H4C | 0.950 | C15—C16 | 1.4972 (18) |
| | | |
C5—N1—C8 | 121.20 (13) | H8A—C8—H8B | 109.5 |
C5—N1—C9 | 120.10 (12) | H8A—C8—H8C | 109.5 |
C8—N1—C9 | 118.58 (13) | H8B—C8—H8C | 109.5 |
H2A—N2—H2B | 119.1 (16) | N1—C9—H9A | 109.5 |
H2A—N2—C17 | 120.9 (10) | N1—C9—H9B | 109.5 |
H2B—N2—C17 | 119.9 (12) | N1—C9—H9C | 109.5 |
C17—N3—C18 | 114.98 (11) | H9A—C9—H9B | 109.5 |
H4A—N4—H4B | 121.4 (16) | H9A—C9—H9C | 109.5 |
H4A—N4—C18 | 119.8 (12) | H9B—C9—H9C | 109.5 |
H4B—N4—C18 | 118.8 (11) | H10—C10—C11 | 119.8 |
C16—N5—C17 | 114.48 (11) | H10—C10—C15 | 119.8 |
C16—N6—C18 | 113.87 (11) | C11—C10—C15 | 120.33 (14) |
O1—C1—H1A | 117.5 | C10—C11—H11 | 119.9 |
O1—C1—C2 | 124.97 (13) | C10—C11—C12 | 120.29 (14) |
H1A—C1—C2 | 117.5 | H11—C11—C12 | 119.9 |
C1—C2—C3 | 120.14 (13) | C11—C12—H12 | 120.1 |
C1—C2—C7 | 121.80 (12) | C11—C12—C13 | 119.89 (13) |
C3—C2—C7 | 118.05 (12) | H12—C12—C13 | 120.1 |
C2—C3—H3A | 119.2 | C12—C13—H13 | 119.9 |
C2—C3—C4 | 121.54 (13) | C12—C13—C14 | 120.14 (13) |
H3A—C3—C4 | 119.2 | H13—C13—C14 | 119.9 |
C3—C4—H4C | 119.7 | C13—C14—H14 | 119.8 |
C3—C4—C5 | 120.59 (13) | C13—C14—C15 | 120.33 (12) |
H4C—C4—C5 | 119.7 | H14—C14—C15 | 119.8 |
N1—C5—C4 | 122.19 (13) | C10—C15—C14 | 118.99 (12) |
N1—C5—C6 | 120.36 (13) | C10—C15—C16 | 120.21 (12) |
C4—C5—C6 | 117.45 (12) | C14—C15—C16 | 120.75 (12) |
C5—C6—H6A | 119.4 | N5—C16—N6 | 126.59 (12) |
C5—C6—C7 | 121.17 (13) | N5—C16—C15 | 116.85 (11) |
H6A—C6—C7 | 119.4 | N6—C16—C15 | 116.55 (11) |
C2—C7—C6 | 121.20 (13) | N2—C17—N3 | 118.00 (12) |
C2—C7—H7A | 119.4 | N2—C17—N5 | 117.31 (12) |
C6—C7—H7A | 119.4 | N3—C17—N5 | 124.69 (12) |
N1—C8—H8A | 109.5 | N3—C18—N4 | 116.58 (12) |
N1—C8—H8B | 109.5 | N3—C18—N6 | 125.29 (12) |
N1—C8—H8C | 109.5 | N4—C18—N6 | 118.13 (12) |
| | | |
O1—C1—C2—C3 | 175.17 (14) | C13—C14—C15—C10 | 0.7 (2) |
O1—C1—C2—C7 | −3.6 (2) | C13—C14—C15—C16 | −176.84 (13) |
C1—C2—C3—C4 | −177.88 (13) | C11—C10—C15—C14 | 0.0 (2) |
C7—C2—C3—C4 | 1.0 (2) | C11—C10—C15—C16 | 177.62 (14) |
C2—C3—C4—C5 | −0.8 (2) | C18—N6—C16—N5 | 2.8 (2) |
C8—N1—C5—C4 | −1.3 (2) | C18—N6—C16—C15 | −175.79 (11) |
C8—N1—C5—C6 | 179.27 (15) | C17—N5—C16—N6 | −0.7 (2) |
C9—N1—C5—C4 | −177.29 (14) | C17—N5—C16—C15 | 177.90 (11) |
C9—N1—C5—C6 | 3.3 (2) | C10—C15—C16—N5 | 169.71 (13) |
C3—C4—C5—N1 | −179.15 (14) | C10—C15—C16—N6 | −11.58 (19) |
C3—C4—C5—C6 | 0.2 (2) | C14—C15—C16—N5 | −12.76 (19) |
N1—C5—C6—C7 | 179.48 (14) | C14—C15—C16—N6 | 165.95 (12) |
C4—C5—C6—C7 | 0.1 (2) | C18—N3—C17—N2 | 179.91 (12) |
C5—C6—C7—C2 | 0.1 (2) | C18—N3—C17—N5 | 0.34 (19) |
C1—C2—C7—C6 | 178.18 (13) | C16—N5—C17—N2 | 179.37 (12) |
C3—C2—C7—C6 | −0.6 (2) | C16—N5—C17—N3 | −1.05 (19) |
C15—C10—C11—C12 | −0.9 (3) | C17—N3—C18—N4 | −177.70 (13) |
C10—C11—C12—C13 | 0.9 (3) | C17—N3—C18—N6 | 2.2 (2) |
C11—C12—C13—C14 | −0.2 (2) | C16—N6—C18—N3 | −3.6 (2) |
C12—C13—C14—C15 | −0.7 (2) | C16—N6—C18—N4 | 176.28 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N5i | 0.902 (17) | 2.066 (18) | 2.9585 (18) | 169.8 (15) |
N2—H2B···O1ii | 0.855 (19) | 2.173 (19) | 2.9990 (16) | 162.4 (16) |
N4—H4A···O1 | 0.917 (19) | 2.132 (19) | 2.8575 (17) | 135.2 (15) |
N4—H4B···N3ii | 0.89 (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 formula | C9H11NO·C9H9N5 |
Mr | 336.40 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 150 |
a, b, c (Å) | 15.848 (3), 10.689 (2), 20.078 (5) |
β (°) | 91.380 (11) |
V (Å3) | 3400.3 (13) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
|
Data collection |
Diffractometer | Bruker SMART 1K CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14907, 4131, 3134 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.669 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.129, 1.05 |
No. of reflections | 4131 |
No. of parameters | 244 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.35, −0.23 |
Selected geometric parameters (Å, º) topN2—C17 | 1.3355 (17) | N5—C16 | 1.3363 (16) |
N3—C17 | 1.3392 (17) | N5—C17 | 1.3598 (16) |
N3—C18 | 1.3469 (17) | N6—C16 | 1.3323 (17) |
N4—C18 | 1.3292 (18) | N6—C18 | 1.3575 (17) |
| | | |
C17—N3—C18 | 114.98 (11) | N5—C16—N6 | 126.59 (12) |
C16—N5—C17 | 114.48 (11) | N3—C17—N5 | 124.69 (12) |
C16—N6—C18 | 113.87 (11) | N3—C18—N6 | 125.29 (12) |
| | | |
O1—C1—C2—C3 | 175.17 (14) | C9—N1—C5—C6 | 3.3 (2) |
O1—C1—C2—C7 | −3.6 (2) | C10—C15—C16—N5 | 169.71 (13) |
C8—N1—C5—C4 | −1.3 (2) | C10—C15—C16—N6 | −11.58 (19) |
C8—N1—C5—C6 | 179.27 (15) | C14—C15—C16—N5 | −12.76 (19) |
C9—N1—C5—C4 | −177.29 (14) | C14—C15—C16—N6 | 165.95 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N5i | 0.902 (17) | 2.066 (18) | 2.9585 (18) | 169.8 (15) |
N2—H2B···O1ii | 0.855 (19) | 2.173 (19) | 2.9990 (16) | 162.4 (16) |
N4—H4A···O1 | 0.917 (19) | 2.132 (19) | 2.8575 (17) | 135.2 (15) |
N4—H4B···N3ii | 0.89 (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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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 π–π 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 π–π 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.