organic compounds
2,2′-{[2-(Pyridin-2-yl)-1,3-diazinane-1,3-diyl]bis(methylene)}diphenol
aDepto. de Química, Universidade Federal de Santa Catarina, 88040-900 - Florianópolis, SC, Brazil
*Correspondence e-mail: adailton.bortoluzzi@ufsc.br
The title compound, C23H25N3O2, was obtained as an intermediary in the preparation of non-symmetric tertiary diamines. The molecular structure presents T-shaped spatial form, in which the pyrimidine ring exhibits a chair conformation. The pyridyl ring is almost perpendicular to the phenyl rings with dihedral angles of 80.17 (8) and 76.03 (2)°. The phenol and amine groups are involved in two strong intramolecular O—H⋯N interactions. In the crystal, the molecules are stacked along [010]; however, no intermolecular interactions are observed.
Related literature
For the synthetic procedure, see: Hureau et al. (2008). For related structures, see: Yokoyama et al. (1995); Xia et al. (2007). For standard bond lengths and angles, see: Bruno et al. (2004).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell SET4 in CAD-4 Software; data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812035477/lr2078sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035477/lr2078Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035477/lr2078Isup3.mol
Supporting information file. DOI: 10.1107/S1600536812035477/lr2078Isup4.cml
Compound (I) was synthesized according to the procedure described by Hureau et al. (2008).
A solution containing 6.0 g of N,N'-bis(2-hydroxybenzyl)-1,3-diamino-propane (21,3 mmol) and 2.39 g (21,3 mmol) of 2-pyridinecarboxaldehyde in 60 ml of MeOH was stirred at temperature of 333,15 K for 1 h. The solvent was evaporated under reduced pressure to afford a white precipitate, which was filtered off and washed with dry diethyl eter. (85% yield = 85%). MP 154.6–154.9 °C, EA for C23H25N3O2: calc C 73,53%; H 7,18%; N 11,27%, found C, 73.57%; H, 6.71%; N, 11.195.
H atoms attached to carbon atoms were placed at their idealized positions with distances of 0.98 and 0.97 Å and Uiso fixed at 1.2 times of Ueq of the preceding atom for CH and CH2, respectively. H atoms of the hydroxyl groups were found from difference map and treated with riding model and their Uiso were fixed at 1.2 times of Ueq of the parent atom.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
SET4 in CAD-4 Software (Enraf–Nonius, 1989); data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Figure 1. The molecular structure of the title compound. Ellipsoids are shown at the 40% probability level. |
C23H25N3O2 | F(000) = 800 |
Mr = 375.46 | Dx = 1.236 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 18.7615 (16) Å | θ = 5.5–17.4° |
b = 6.2105 (11) Å | µ = 0.08 mm−1 |
c = 19.0407 (12) Å | T = 293 K |
β = 114.594 (8)° | Block, colorless |
V = 2017.3 (4) Å3 | 0.50 × 0.50 × 0.40 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.079 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 1.3° |
Graphite monochromator | h = −20→22 |
ω–2θ scans | k = −7→0 |
3711 measured reflections | l = −22→0 |
3595 independent reflections | 3 standard reflections every 200 reflections |
2038 reflections with I > 2σ(I) | intensity decay: 1% |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0711P)2 + 0.2051P] where P = (Fo2 + 2Fc2)/3 |
3595 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C23H25N3O2 | V = 2017.3 (4) Å3 |
Mr = 375.46 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 18.7615 (16) Å | µ = 0.08 mm−1 |
b = 6.2105 (11) Å | T = 293 K |
c = 19.0407 (12) Å | 0.50 × 0.50 × 0.40 mm |
β = 114.594 (8)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.079 |
3711 measured reflections | 3 standard reflections every 200 reflections |
3595 independent reflections | intensity decay: 1% |
2038 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.17 e Å−3 |
3595 reflections | Δρmin = −0.21 e Å−3 |
253 parameters |
x | y | z | Uiso*/Ueq | ||
N1 | 0.65802 (10) | 0.2353 (3) | −0.10455 (10) | 0.0445 (5) | |
C2 | 0.57867 (13) | 0.1394 (4) | −0.14032 (13) | 0.0545 (7) | |
H2A | 0.5828 | −0.0130 | −0.1492 | 0.065* | |
H2B | 0.5488 | 0.2073 | −0.1898 | 0.065* | |
C3 | 0.53699 (14) | 0.1696 (5) | −0.08857 (14) | 0.0636 (8) | |
H3A | 0.5285 | 0.3218 | −0.0835 | 0.076* | |
H3B | 0.4863 | 0.0989 | −0.1109 | 0.076* | |
C4 | 0.58552 (14) | 0.0754 (5) | −0.01042 (14) | 0.0631 (8) | |
H4A | 0.5594 | 0.0982 | 0.0235 | 0.076* | |
H4B | 0.5914 | −0.0784 | −0.0151 | 0.076* | |
N5 | 0.66299 (10) | 0.1781 (3) | 0.02244 (11) | 0.0481 (5) | |
C10 | 0.69848 (14) | 0.2035 (4) | −0.15583 (14) | 0.0528 (6) | |
H10A | 0.6964 | 0.0521 | −0.1691 | 0.063* | |
H10B | 0.7532 | 0.2433 | −0.1283 | 0.063* | |
C11 | 0.66255 (14) | 0.3345 (4) | −0.22904 (13) | 0.0504 (6) | |
C12 | 0.63385 (15) | 0.5401 (4) | −0.22823 (15) | 0.0581 (7) | |
C13 | 0.60453 (16) | 0.6654 (5) | −0.29458 (16) | 0.0697 (8) | |
H13 | 0.5838 | 0.8009 | −0.2938 | 0.084* | |
C14 | 0.60633 (17) | 0.5889 (6) | −0.36109 (17) | 0.0781 (9) | |
H14 | 0.5881 | 0.6747 | −0.4051 | 0.094* | |
C15 | 0.63473 (17) | 0.3875 (6) | −0.36363 (16) | 0.0741 (9) | |
H15 | 0.6353 | 0.3361 | −0.4093 | 0.089* | |
C16 | 0.66272 (15) | 0.2605 (5) | −0.29765 (15) | 0.0635 (7) | |
H16 | 0.6819 | 0.1235 | −0.2995 | 0.076* | |
C20 | 0.70860 (14) | 0.0956 (4) | 0.10175 (13) | 0.0536 (7) | |
H20A | 0.7614 | 0.1532 | 0.1214 | 0.064* | |
H20B | 0.7121 | −0.0600 | 0.1000 | 0.064* | |
C21 | 0.67202 (13) | 0.1560 (4) | 0.15583 (13) | 0.0479 (6) | |
C22 | 0.64091 (15) | 0.3595 (5) | 0.15448 (14) | 0.0564 (7) | |
C23 | 0.61059 (16) | 0.4140 (5) | 0.20724 (16) | 0.0689 (8) | |
H23 | 0.5892 | 0.5500 | 0.2057 | 0.083* | |
C24 | 0.61217 (17) | 0.2666 (6) | 0.26183 (16) | 0.0735 (8) | |
H24 | 0.5921 | 0.3038 | 0.2974 | 0.088* | |
C25 | 0.64312 (17) | 0.0652 (5) | 0.26416 (15) | 0.0703 (8) | |
H25 | 0.6443 | −0.0341 | 0.3012 | 0.084* | |
C26 | 0.67240 (14) | 0.0119 (4) | 0.21108 (13) | 0.0568 (7) | |
H26 | 0.6930 | −0.1250 | 0.2125 | 0.068* | |
C30 | 0.70474 (12) | 0.1435 (4) | −0.02717 (12) | 0.0443 (6) | |
H30 | 0.7115 | −0.0114 | −0.0321 | 0.053* | |
C31 | 0.78452 (13) | 0.2502 (4) | 0.00853 (13) | 0.0451 (6) | |
N32 | 0.84615 (11) | 0.1185 (3) | 0.03432 (12) | 0.0549 (6) | |
C33 | 0.91701 (15) | 0.2096 (5) | 0.06679 (17) | 0.0691 (8) | |
H33 | 0.9605 | 0.1195 | 0.0861 | 0.083* | |
C34 | 0.92949 (17) | 0.4257 (6) | 0.07337 (17) | 0.0740 (9) | |
H34 | 0.9801 | 0.4810 | 0.0955 | 0.089* | |
C35 | 0.86581 (17) | 0.5606 (5) | 0.04665 (14) | 0.0638 (8) | |
H35 | 0.8723 | 0.7092 | 0.0505 | 0.077* | |
C36 | 0.79262 (15) | 0.4714 (4) | 0.01433 (14) | 0.0550 (7) | |
H36 | 0.7485 | 0.5592 | −0.0037 | 0.066* | |
O10 | 0.63242 (12) | 0.6251 (3) | −0.16299 (11) | 0.0789 (6) | |
H10 | 0.6485 | 0.5027 | −0.1240 | 0.095* | |
O20 | 0.63844 (12) | 0.5107 (3) | 0.10137 (11) | 0.0754 (6) | |
H20 | 0.6531 | 0.4237 | 0.0597 | 0.090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0433 (11) | 0.0465 (11) | 0.0424 (10) | 0.0008 (9) | 0.0167 (9) | 0.0002 (9) |
C2 | 0.0463 (14) | 0.0617 (17) | 0.0479 (13) | −0.0021 (13) | 0.0120 (11) | 0.0025 (13) |
C3 | 0.0396 (13) | 0.093 (2) | 0.0531 (15) | −0.0052 (14) | 0.0141 (12) | 0.0054 (15) |
C4 | 0.0490 (15) | 0.084 (2) | 0.0529 (15) | −0.0118 (14) | 0.0176 (12) | 0.0097 (15) |
N5 | 0.0394 (11) | 0.0558 (13) | 0.0452 (11) | −0.0027 (10) | 0.0136 (9) | 0.0079 (10) |
C10 | 0.0543 (15) | 0.0494 (15) | 0.0565 (15) | 0.0046 (12) | 0.0249 (13) | −0.0022 (12) |
C11 | 0.0479 (14) | 0.0565 (16) | 0.0476 (14) | −0.0053 (12) | 0.0206 (11) | −0.0021 (13) |
C12 | 0.0621 (17) | 0.0532 (16) | 0.0529 (16) | −0.0021 (14) | 0.0178 (13) | 0.0038 (14) |
C13 | 0.0732 (19) | 0.0683 (19) | 0.0600 (17) | −0.0021 (16) | 0.0202 (15) | 0.0139 (16) |
C14 | 0.069 (2) | 0.100 (3) | 0.0585 (19) | −0.0141 (19) | 0.0190 (15) | 0.0212 (19) |
C15 | 0.0710 (19) | 0.108 (3) | 0.0508 (17) | −0.022 (2) | 0.0330 (15) | −0.0036 (18) |
C16 | 0.0602 (16) | 0.078 (2) | 0.0611 (17) | −0.0102 (15) | 0.0337 (14) | −0.0119 (16) |
C20 | 0.0468 (14) | 0.0567 (16) | 0.0479 (14) | 0.0035 (12) | 0.0104 (11) | 0.0101 (13) |
C21 | 0.0412 (13) | 0.0541 (15) | 0.0392 (13) | −0.0039 (12) | 0.0076 (10) | 0.0041 (12) |
C22 | 0.0530 (15) | 0.0593 (17) | 0.0517 (15) | 0.0035 (14) | 0.0167 (12) | 0.0081 (14) |
C23 | 0.0653 (18) | 0.073 (2) | 0.0637 (17) | 0.0132 (16) | 0.0224 (15) | 0.0025 (16) |
C24 | 0.074 (2) | 0.094 (2) | 0.0539 (17) | 0.0093 (19) | 0.0283 (15) | 0.0021 (18) |
C25 | 0.0755 (19) | 0.085 (2) | 0.0472 (15) | 0.0029 (18) | 0.0225 (14) | 0.0134 (16) |
C26 | 0.0556 (15) | 0.0609 (17) | 0.0450 (14) | 0.0030 (13) | 0.0121 (12) | 0.0065 (13) |
C30 | 0.0408 (13) | 0.0365 (12) | 0.0505 (14) | 0.0009 (11) | 0.0140 (11) | 0.0029 (11) |
C31 | 0.0461 (14) | 0.0459 (15) | 0.0437 (13) | 0.0016 (12) | 0.0191 (11) | 0.0029 (12) |
N32 | 0.0421 (12) | 0.0536 (13) | 0.0643 (13) | 0.0055 (11) | 0.0176 (10) | 0.0002 (11) |
C33 | 0.0424 (16) | 0.077 (2) | 0.078 (2) | 0.0063 (15) | 0.0156 (14) | −0.0024 (17) |
C34 | 0.0540 (17) | 0.093 (3) | 0.0694 (19) | −0.0226 (18) | 0.0199 (15) | −0.0098 (18) |
C35 | 0.076 (2) | 0.0546 (17) | 0.0557 (16) | −0.0227 (16) | 0.0219 (15) | −0.0059 (14) |
C36 | 0.0592 (17) | 0.0457 (16) | 0.0567 (15) | 0.0011 (13) | 0.0207 (13) | 0.0039 (13) |
O10 | 0.1205 (17) | 0.0512 (12) | 0.0618 (12) | 0.0213 (12) | 0.0346 (12) | 0.0043 (10) |
O20 | 0.0978 (15) | 0.0595 (12) | 0.0769 (13) | 0.0172 (11) | 0.0444 (11) | 0.0199 (11) |
N1—C10 | 1.478 (3) | C20—C21 | 1.504 (3) |
N1—C30 | 1.480 (3) | C20—H20A | 0.9700 |
N1—C2 | 1.480 (3) | C20—H20B | 0.9700 |
C2—C3 | 1.503 (3) | C21—C26 | 1.379 (3) |
C2—H2A | 0.9700 | C21—C22 | 1.388 (4) |
C2—H2B | 0.9700 | C22—O20 | 1.367 (3) |
C3—C4 | 1.503 (3) | C22—C23 | 1.387 (4) |
C3—H3A | 0.9700 | C23—C24 | 1.376 (4) |
C3—H3B | 0.9700 | C23—H23 | 0.9300 |
C4—N5 | 1.468 (3) | C24—C25 | 1.372 (4) |
C4—H4A | 0.9700 | C24—H24 | 0.9300 |
C4—H4B | 0.9700 | C25—C26 | 1.376 (4) |
N5—C30 | 1.472 (3) | C25—H25 | 0.9300 |
N5—C20 | 1.483 (3) | C26—H26 | 0.9300 |
C10—C11 | 1.509 (3) | C30—C31 | 1.515 (3) |
C10—H10A | 0.9700 | C30—H30 | 0.9800 |
C10—H10B | 0.9700 | C31—N32 | 1.332 (3) |
C11—C16 | 1.386 (3) | C31—C36 | 1.382 (3) |
C11—C12 | 1.388 (4) | N32—C33 | 1.336 (3) |
C12—O10 | 1.360 (3) | C33—C34 | 1.359 (4) |
C12—C13 | 1.388 (4) | C33—H33 | 0.9300 |
C13—C14 | 1.366 (4) | C34—C35 | 1.372 (4) |
C13—H13 | 0.9300 | C34—H34 | 0.9300 |
C14—C15 | 1.368 (4) | C35—C36 | 1.367 (3) |
C14—H14 | 0.9300 | C35—H35 | 0.9300 |
C15—C16 | 1.388 (4) | C36—H36 | 0.9300 |
C15—H15 | 0.9300 | O10—H10 | 1.0163 |
C16—H16 | 0.9300 | O20—H20 | 1.0857 |
C10—N1—C30 | 110.60 (17) | N5—C20—C21 | 112.13 (19) |
C10—N1—C2 | 109.68 (18) | N5—C20—H20A | 109.2 |
C30—N1—C2 | 111.63 (18) | C21—C20—H20A | 109.2 |
N1—C2—C3 | 110.3 (2) | N5—C20—H20B | 109.2 |
N1—C2—H2A | 109.6 | C21—C20—H20B | 109.2 |
C3—C2—H2A | 109.6 | H20A—C20—H20B | 107.9 |
N1—C2—H2B | 109.6 | C26—C21—C22 | 118.3 (2) |
C3—C2—H2B | 109.6 | C26—C21—C20 | 120.1 (2) |
H2A—C2—H2B | 108.1 | C22—C21—C20 | 121.5 (2) |
C4—C3—C2 | 109.6 (2) | O20—C22—C23 | 118.1 (3) |
C4—C3—H3A | 109.8 | O20—C22—C21 | 121.6 (2) |
C2—C3—H3A | 109.8 | C23—C22—C21 | 120.3 (3) |
C4—C3—H3B | 109.8 | C24—C23—C22 | 119.9 (3) |
C2—C3—H3B | 109.8 | C24—C23—H23 | 120.0 |
H3A—C3—H3B | 108.2 | C22—C23—H23 | 120.0 |
N5—C4—C3 | 109.7 (2) | C25—C24—C23 | 120.4 (3) |
N5—C4—H4A | 109.7 | C25—C24—H24 | 119.8 |
C3—C4—H4A | 109.7 | C23—C24—H24 | 119.8 |
N5—C4—H4B | 109.7 | C24—C25—C26 | 119.2 (3) |
C3—C4—H4B | 109.7 | C24—C25—H25 | 120.4 |
H4A—C4—H4B | 108.2 | C26—C25—H25 | 120.4 |
C4—N5—C30 | 111.11 (18) | C25—C26—C21 | 121.8 (3) |
C4—N5—C20 | 109.47 (18) | C25—C26—H26 | 119.1 |
C30—N5—C20 | 111.56 (18) | C21—C26—H26 | 119.1 |
N1—C10—C11 | 112.53 (19) | N5—C30—N1 | 109.26 (17) |
N1—C10—H10A | 109.1 | N5—C30—C31 | 109.79 (18) |
C11—C10—H10A | 109.1 | N1—C30—C31 | 110.09 (18) |
N1—C10—H10B | 109.1 | N5—C30—H30 | 109.2 |
C11—C10—H10B | 109.1 | N1—C30—H30 | 109.2 |
H10A—C10—H10B | 107.8 | C31—C30—H30 | 109.2 |
C16—C11—C12 | 117.9 (2) | N32—C31—C36 | 122.1 (2) |
C16—C11—C10 | 121.1 (2) | N32—C31—C30 | 116.2 (2) |
C12—C11—C10 | 120.8 (2) | C36—C31—C30 | 121.7 (2) |
O10—C12—C13 | 117.6 (3) | C31—N32—C33 | 117.1 (2) |
O10—C12—C11 | 121.5 (2) | N32—C33—C34 | 124.1 (3) |
C13—C12—C11 | 120.9 (3) | N32—C33—H33 | 118.0 |
C14—C13—C12 | 119.7 (3) | C34—C33—H33 | 118.0 |
C14—C13—H13 | 120.1 | C33—C34—C35 | 118.6 (3) |
C12—C13—H13 | 120.1 | C33—C34—H34 | 120.7 |
C13—C14—C15 | 120.7 (3) | C35—C34—H34 | 120.7 |
C13—C14—H14 | 119.6 | C36—C35—C34 | 118.4 (3) |
C15—C14—H14 | 119.6 | C36—C35—H35 | 120.8 |
C14—C15—C16 | 119.6 (3) | C34—C35—H35 | 120.8 |
C14—C15—H15 | 120.2 | C35—C36—C31 | 119.7 (3) |
C16—C15—H15 | 120.2 | C35—C36—H36 | 120.1 |
C11—C16—C15 | 121.1 (3) | C31—C36—H36 | 120.1 |
C11—C16—H16 | 119.5 | C12—O10—H10 | 105.3 |
C15—C16—H16 | 119.5 | C22—O20—H20 | 104.9 |
C10—N1—C2—C3 | 179.7 (2) | C20—C21—C22—C23 | −177.2 (2) |
C30—N1—C2—C3 | 56.7 (3) | O20—C22—C23—C24 | −179.8 (3) |
N1—C2—C3—C4 | −56.0 (3) | C21—C22—C23—C24 | 0.8 (4) |
C2—C3—C4—N5 | 57.8 (3) | C22—C23—C24—C25 | −0.4 (4) |
C3—C4—N5—C30 | −60.3 (3) | C23—C24—C25—C26 | −0.2 (4) |
C3—C4—N5—C20 | 176.1 (2) | C24—C25—C26—C21 | 0.5 (4) |
C30—N1—C10—C11 | −167.62 (19) | C22—C21—C26—C25 | −0.1 (4) |
C2—N1—C10—C11 | 68.8 (2) | C20—C21—C26—C25 | 176.6 (2) |
N1—C10—C11—C16 | −148.2 (2) | C4—N5—C30—N1 | 59.5 (2) |
N1—C10—C11—C12 | 36.9 (3) | C20—N5—C30—N1 | −178.04 (17) |
C16—C11—C12—O10 | −179.3 (2) | C4—N5—C30—C31 | −179.67 (19) |
C10—C11—C12—O10 | −4.3 (4) | C20—N5—C30—C31 | −57.2 (2) |
C16—C11—C12—C13 | 1.5 (4) | C10—N1—C30—N5 | 179.92 (18) |
C10—C11—C12—C13 | 176.6 (2) | C2—N1—C30—N5 | −57.7 (2) |
O10—C12—C13—C14 | 178.5 (2) | C10—N1—C30—C31 | 59.3 (2) |
C11—C12—C13—C14 | −2.3 (4) | C2—N1—C30—C31 | −178.30 (19) |
C12—C13—C14—C15 | 1.8 (4) | N5—C30—C31—N32 | 111.9 (2) |
C13—C14—C15—C16 | −0.6 (4) | N1—C30—C31—N32 | −127.7 (2) |
C12—C11—C16—C15 | −0.3 (4) | N5—C30—C31—C36 | −67.7 (3) |
C10—C11—C16—C15 | −175.4 (2) | N1—C30—C31—C36 | 52.7 (3) |
C14—C15—C16—C11 | −0.1 (4) | C36—C31—N32—C33 | 0.3 (4) |
C4—N5—C20—C21 | −64.3 (3) | C30—C31—N32—C33 | −179.3 (2) |
C30—N5—C20—C21 | 172.29 (19) | C31—N32—C33—C34 | −1.4 (4) |
N5—C20—C21—C26 | 141.8 (2) | N32—C33—C34—C35 | 1.4 (5) |
N5—C20—C21—C22 | −41.6 (3) | C33—C34—C35—C36 | −0.2 (4) |
C26—C21—C22—O20 | −179.9 (2) | C34—C35—C36—C31 | −0.7 (4) |
C20—C21—C22—O20 | 3.4 (4) | N32—C31—C36—C35 | 0.7 (4) |
C26—C21—C22—C23 | −0.5 (4) | C30—C31—C36—C35 | −179.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O10—H10···N1 | 1.02 | 1.69 | 2.624 (3) | 150 |
O20—H20···N5 | 1.09 | 1.72 | 2.705 (3) | 148 |
Experimental details
Crystal data | |
Chemical formula | C23H25N3O2 |
Mr | 375.46 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 18.7615 (16), 6.2105 (11), 19.0407 (12) |
β (°) | 114.594 (8) |
V (Å3) | 2017.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.50 × 0.40 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3711, 3595, 2038 |
Rint | 0.079 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.146, 1.01 |
No. of reflections | 3595 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.21 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), SET4 in CAD-4 Software (Enraf–Nonius, 1989), HELENA (Spek, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O10—H10···N1 | 1.02 | 1.69 | 2.624 (3) | 150 |
O20—H20···N5 | 1.09 | 1.72 | 2.705 (3) | 148 |
Acknowledgements
The authors thank the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and the Financiadora de Estudos e Projetos (FINEP) for financial support.
References
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The molecular structure of the title compound (I) shows T-shaped spatial form (Fig. 1). Pyrimidine ring adopts regular chair conformation with square plane formed by N1/C2/C4/C5 atoms (r.m.s. deviation = 0.0111).
The dihedral angles between the mean planes of the rings C31/C36 and C11/C16 of 80.17 (8)° and C31/36 and C211/C26 of 76.03 (8)° demonstrate that pyridil ring is almost perpendicular to phenol groups.
Two strong intramolecular O—H···N hydrogen bonds between phenol and amine groups (Table 1) form additional six-membered rings, which contribute for the rigidity of the structure and avoid the crystal supramolecurity.
The molecules are stacked along [010] direction, however no further intermolecular interactions, such as π-stacking, were observed.
All bond lengths and angles found for (I) are in the expected range for organic compounds (Bruno et al., 2004).