Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054037/ci2492sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054037/ci2492Isup2.hkl |
CCDC reference: 674074
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.074
- wR factor = 0.216
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C17 ... 1.42 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 60
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Colpaert (2003); Doria et al. (1983); Hermecz et al. (1996); Hermecz & Meszaros (1988); Knoll et al. (1987); Kozlovskaya et al. (1995).
The title compound was prepared by the reaction of 4-chlorobenzaldehyde (0.141 g, 1 mmol), 2-(5,5-dimethyl-3-oxocyclohex-1-enylamino)benzoic acid (0.259 g, 1 mmol) with malononitrile (0.066 g, 1 mmol) in ethylene glycol (2.0 ml) at 393 K under microwave irradiation (maximum power 200 W, initial power 100 W) for 6 min (yield; 0.370 g, 86%, m.p. 513–515 K). Single crystals suitable for X-ray analysis were obtained from an ethanol-DMF solution by slow evaporation.
H atoms were positioned geometrically (N—H = 0.86 Å and C—H = 0.93–0.98 Å) and treated as riding, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N) for others. Non-H atoms of the solvent molecule were restrained to have the same Uij components within 0.01 Å2.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).
Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. | |
Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. |
C25H20ClN3O2·C3H7NO | F(000) = 2112 |
Mr = 502.99 | Dx = 1.348 Mg m−3 |
Monoclinic, C2/c | Melting point = 513–515 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 36.340 (15) Å | Cell parameters from 2136 reflections |
b = 11.780 (5) Å | θ = 2.4–25.3° |
c = 11.870 (5) Å | µ = 0.19 mm−1 |
β = 102.714 (5)° | T = 298 K |
V = 4957 (4) Å3 | Block, colourless |
Z = 8 | 0.23 × 0.14 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 4326 independent reflections |
Radiation source: fine-focus sealed tube | 2288 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −42→43 |
Tmin = 0.957, Tmax = 0.981 | k = −13→11 |
12316 measured reflections | l = −14→13 |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.216 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1126P)2] where P = (Fo2 + 2Fc2)/3 |
4326 reflections | (Δ/σ)max = 0.001 |
325 parameters | Δρmax = 0.34 e Å−3 |
60 restraints | Δρmin = −0.42 e Å−3 |
C25H20ClN3O2·C3H7NO | V = 4957 (4) Å3 |
Mr = 502.99 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 36.340 (15) Å | µ = 0.19 mm−1 |
b = 11.780 (5) Å | T = 298 K |
c = 11.870 (5) Å | 0.23 × 0.14 × 0.10 mm |
β = 102.714 (5)° |
Bruker SMART CCD area-detector diffractometer | 4326 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2288 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.981 | Rint = 0.063 |
12316 measured reflections |
R[F2 > 2σ(F2)] = 0.074 | 60 restraints |
wR(F2) = 0.216 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.34 e Å−3 |
4326 reflections | Δρmin = −0.42 e Å−3 |
325 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.22931 (4) | 0.20405 (11) | 0.35844 (12) | 0.0610 (4) | |
N1 | 0.10967 (9) | 0.6994 (3) | 0.4721 (3) | 0.0318 (8) | |
N2 | 0.05505 (9) | 0.6470 (3) | 0.3342 (3) | 0.0377 (9) | |
H2 | 0.0443 | 0.6346 | 0.2631 | 0.045* | |
N3 | 0.09005 (14) | 0.6117 (4) | 0.0656 (4) | 0.0663 (13) | |
N4 | 0.0483 (2) | 0.0499 (6) | 0.5512 (7) | 0.120 (2) | |
O1 | 0.22370 (9) | 0.7976 (3) | 0.3680 (3) | 0.0526 (9) | |
O2 | −0.00184 (9) | 0.6354 (3) | 0.3812 (3) | 0.0583 (10) | |
O3 | 0.04761 (18) | −0.0973 (5) | 0.4284 (6) | 0.1298 (19) | |
C1 | 0.09373 (11) | 0.6650 (3) | 0.3591 (4) | 0.0307 (10) | |
C2 | 0.11552 (11) | 0.6560 (4) | 0.2798 (4) | 0.0330 (10) | |
C3 | 0.15792 (11) | 0.6684 (3) | 0.3142 (4) | 0.0334 (10) | |
H3 | 0.1660 | 0.7058 | 0.2499 | 0.040* | |
C4 | 0.16683 (11) | 0.7482 (3) | 0.4158 (4) | 0.0318 (10) | |
C5 | 0.20159 (12) | 0.8182 (4) | 0.4284 (4) | 0.0374 (11) | |
C6 | 0.20743 (12) | 0.9120 (4) | 0.5151 (4) | 0.0434 (12) | |
H6A | 0.2204 | 0.9740 | 0.4865 | 0.052* | |
H6B | 0.2236 | 0.8849 | 0.5861 | 0.052* | |
C7 | 0.17098 (12) | 0.9572 (4) | 0.5417 (4) | 0.0406 (11) | |
C8 | 0.15012 (13) | 0.8553 (4) | 0.5792 (4) | 0.0401 (11) | |
H8A | 0.1648 | 0.8252 | 0.6512 | 0.048* | |
H8B | 0.1260 | 0.8804 | 0.5926 | 0.048* | |
C9 | 0.14360 (11) | 0.7626 (3) | 0.4891 (3) | 0.0306 (10) | |
C10 | 0.03270 (12) | 0.6470 (4) | 0.4115 (4) | 0.0412 (11) | |
C11 | 0.05214 (11) | 0.6549 (4) | 0.5329 (4) | 0.0357 (10) | |
C12 | 0.09081 (11) | 0.6765 (3) | 0.5618 (4) | 0.0326 (10) | |
C13 | 0.10988 (13) | 0.6722 (4) | 0.6773 (4) | 0.0393 (11) | |
H13 | 0.1359 | 0.6828 | 0.6979 | 0.047* | |
C14 | 0.08950 (13) | 0.6519 (4) | 0.7605 (4) | 0.0478 (12) | |
H14 | 0.1020 | 0.6514 | 0.8379 | 0.057* | |
C15 | 0.05093 (14) | 0.6324 (4) | 0.7322 (5) | 0.0560 (14) | |
H15 | 0.0377 | 0.6198 | 0.7896 | 0.067* | |
C16 | 0.03289 (14) | 0.6318 (4) | 0.6192 (4) | 0.0503 (13) | |
H16 | 0.0072 | 0.6157 | 0.5993 | 0.060* | |
C17 | 0.09971 (13) | 0.6297 (4) | 0.1621 (4) | 0.0415 (11) | |
C18 | 0.17739 (12) | 0.5544 (3) | 0.3316 (4) | 0.0335 (10) | |
C19 | 0.19864 (12) | 0.5168 (4) | 0.2540 (4) | 0.0401 (11) | |
H19 | 0.2019 | 0.5651 | 0.1951 | 0.048* | |
C20 | 0.21478 (12) | 0.4114 (4) | 0.2618 (4) | 0.0439 (12) | |
H20 | 0.2287 | 0.3882 | 0.2089 | 0.053* | |
C21 | 0.21002 (12) | 0.3403 (4) | 0.3495 (4) | 0.0410 (11) | |
C22 | 0.18959 (13) | 0.3743 (4) | 0.4295 (4) | 0.0449 (12) | |
H22 | 0.1867 | 0.3259 | 0.4889 | 0.054* | |
C23 | 0.17380 (13) | 0.4804 (4) | 0.4195 (4) | 0.0418 (12) | |
H23 | 0.1602 | 0.5037 | 0.4734 | 0.050* | |
C24 | 0.17994 (15) | 1.0424 (4) | 0.6416 (5) | 0.0585 (14) | |
H24A | 0.1568 | 1.0703 | 0.6578 | 0.088* | |
H24B | 0.1941 | 1.1046 | 0.6206 | 0.088* | |
H24C | 0.1945 | 1.0055 | 0.7090 | 0.088* | |
C25 | 0.14643 (14) | 1.0169 (4) | 0.4364 (5) | 0.0555 (14) | |
H25A | 0.1236 | 1.0437 | 0.4557 | 0.083* | |
H25B | 0.1403 | 0.9642 | 0.3733 | 0.083* | |
H25C | 0.1600 | 1.0799 | 0.4144 | 0.083* | |
C26 | 0.0489 (3) | −0.0566 (8) | 0.5279 (10) | 0.125 (3) | |
H26 | 0.0503 | −0.1075 | 0.5886 | 0.150* | |
C27 | 0.0500 (3) | 0.0870 (9) | 0.6655 (9) | 0.163 (3) | |
H27A | 0.0484 | 0.1683 | 0.6667 | 0.244* | |
H27B | 0.0733 | 0.0628 | 0.7143 | 0.244* | |
H27C | 0.0293 | 0.0550 | 0.6930 | 0.244* | |
C28 | 0.0440 (3) | 0.1374 (7) | 0.4606 (9) | 0.144 (3) | |
H28A | 0.0435 | 0.2111 | 0.4948 | 0.217* | |
H28B | 0.0208 | 0.1251 | 0.4048 | 0.217* | |
H28C | 0.0648 | 0.1331 | 0.4232 | 0.217* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0635 (9) | 0.0489 (8) | 0.0656 (9) | 0.0194 (6) | 0.0034 (7) | −0.0071 (7) |
N1 | 0.0321 (19) | 0.038 (2) | 0.027 (2) | −0.0028 (16) | 0.0105 (16) | −0.0018 (16) |
N2 | 0.030 (2) | 0.050 (2) | 0.032 (2) | −0.0033 (16) | 0.0035 (17) | −0.0042 (17) |
N3 | 0.076 (3) | 0.087 (3) | 0.035 (3) | 0.000 (3) | 0.009 (2) | −0.003 (2) |
N4 | 0.135 (5) | 0.089 (4) | 0.131 (5) | 0.005 (4) | 0.017 (4) | −0.021 (4) |
O1 | 0.0463 (19) | 0.067 (2) | 0.053 (2) | −0.0070 (16) | 0.0300 (18) | −0.0006 (18) |
O2 | 0.0293 (19) | 0.090 (3) | 0.053 (2) | −0.0075 (17) | 0.0044 (16) | 0.0061 (19) |
O3 | 0.158 (5) | 0.098 (4) | 0.134 (5) | 0.008 (3) | 0.033 (4) | −0.011 (3) |
C1 | 0.027 (2) | 0.032 (2) | 0.030 (2) | 0.0022 (17) | 0.0016 (19) | 0.0009 (18) |
C2 | 0.033 (2) | 0.040 (2) | 0.026 (2) | 0.0052 (19) | 0.0060 (19) | 0.0004 (18) |
C3 | 0.032 (2) | 0.044 (3) | 0.026 (2) | 0.0015 (19) | 0.0108 (19) | 0.0036 (19) |
C4 | 0.030 (2) | 0.039 (2) | 0.029 (2) | 0.0024 (18) | 0.0115 (19) | 0.0019 (19) |
C5 | 0.034 (2) | 0.038 (3) | 0.042 (3) | 0.0014 (19) | 0.011 (2) | 0.007 (2) |
C6 | 0.032 (3) | 0.043 (3) | 0.055 (3) | −0.006 (2) | 0.011 (2) | 0.001 (2) |
C7 | 0.040 (3) | 0.043 (3) | 0.041 (3) | −0.005 (2) | 0.013 (2) | −0.002 (2) |
C8 | 0.043 (3) | 0.046 (3) | 0.034 (3) | −0.002 (2) | 0.015 (2) | −0.008 (2) |
C9 | 0.032 (2) | 0.034 (2) | 0.025 (2) | −0.0053 (18) | 0.0035 (19) | 0.0029 (18) |
C10 | 0.030 (3) | 0.047 (3) | 0.047 (3) | −0.005 (2) | 0.008 (2) | 0.002 (2) |
C11 | 0.027 (2) | 0.041 (3) | 0.040 (3) | −0.0006 (19) | 0.009 (2) | 0.002 (2) |
C12 | 0.033 (2) | 0.032 (2) | 0.035 (3) | 0.0010 (18) | 0.012 (2) | 0.0017 (19) |
C13 | 0.039 (3) | 0.045 (3) | 0.034 (3) | −0.002 (2) | 0.010 (2) | 0.002 (2) |
C14 | 0.048 (3) | 0.069 (3) | 0.028 (3) | 0.008 (2) | 0.010 (2) | 0.006 (2) |
C15 | 0.049 (3) | 0.077 (4) | 0.049 (3) | −0.002 (3) | 0.026 (3) | 0.012 (3) |
C16 | 0.042 (3) | 0.067 (3) | 0.046 (3) | −0.004 (2) | 0.018 (3) | 0.006 (3) |
C17 | 0.046 (3) | 0.050 (3) | 0.028 (3) | 0.003 (2) | 0.008 (2) | 0.000 (2) |
C18 | 0.037 (2) | 0.037 (3) | 0.028 (2) | 0.0010 (19) | 0.010 (2) | −0.0007 (19) |
C19 | 0.039 (3) | 0.047 (3) | 0.038 (3) | −0.003 (2) | 0.017 (2) | 0.000 (2) |
C20 | 0.038 (3) | 0.055 (3) | 0.042 (3) | 0.006 (2) | 0.017 (2) | −0.008 (2) |
C21 | 0.039 (3) | 0.041 (3) | 0.042 (3) | 0.007 (2) | 0.006 (2) | −0.008 (2) |
C22 | 0.053 (3) | 0.046 (3) | 0.036 (3) | 0.010 (2) | 0.010 (2) | 0.008 (2) |
C23 | 0.045 (3) | 0.053 (3) | 0.031 (3) | 0.011 (2) | 0.017 (2) | 0.003 (2) |
C24 | 0.065 (4) | 0.053 (3) | 0.060 (4) | −0.016 (3) | 0.018 (3) | −0.019 (3) |
C25 | 0.052 (3) | 0.047 (3) | 0.066 (4) | 0.005 (2) | 0.010 (3) | 0.004 (3) |
C26 | 0.133 (5) | 0.091 (5) | 0.142 (6) | 0.002 (5) | 0.012 (5) | −0.029 (5) |
C27 | 0.181 (7) | 0.156 (7) | 0.143 (7) | −0.010 (6) | 0.015 (7) | −0.042 (6) |
C28 | 0.158 (7) | 0.105 (6) | 0.166 (7) | 0.002 (5) | 0.027 (6) | 0.015 (6) |
Cl1—C21 | 1.745 (5) | C11—C16 | 1.389 (6) |
N1—C1 | 1.398 (5) | C11—C12 | 1.395 (6) |
N1—C12 | 1.413 (5) | C12—C13 | 1.395 (6) |
N1—C9 | 1.417 (5) | C13—C14 | 1.380 (6) |
N2—C10 | 1.352 (5) | C13—H13 | 0.93 |
N2—C1 | 1.388 (5) | C14—C15 | 1.387 (6) |
N2—H2 | 0.86 | C14—H14 | 0.93 |
N3—C17 | 1.142 (6) | C15—C16 | 1.357 (7) |
N4—C26 | 1.286 (10) | C15—H15 | 0.93 |
N4—C27 | 1.414 (11) | C16—H16 | 0.93 |
N4—C28 | 1.473 (10) | C18—C23 | 1.387 (6) |
O1—C5 | 1.214 (5) | C18—C19 | 1.398 (6) |
O2—C10 | 1.235 (5) | C19—C20 | 1.368 (6) |
O3—C26 | 1.266 (10) | C19—H19 | 0.9300 |
C1—C2 | 1.360 (6) | C20—C21 | 1.376 (6) |
C2—C17 | 1.424 (6) | C20—H20 | 0.9300 |
C2—C3 | 1.512 (6) | C21—C22 | 1.388 (6) |
C3—C4 | 1.506 (6) | C22—C23 | 1.370 (6) |
C3—C18 | 1.511 (6) | C22—H22 | 0.93 |
C3—H3 | 0.98 | C23—H23 | 0.93 |
C4—C9 | 1.349 (5) | C24—H24A | 0.96 |
C4—C5 | 1.488 (6) | C24—H24B | 0.96 |
C5—C6 | 1.493 (6) | C24—H24C | 0.96 |
C6—C7 | 1.524 (6) | C25—H25A | 0.96 |
C6—H6A | 0.97 | C25—H25B | 0.96 |
C6—H6B | 0.97 | C25—H25C | 0.96 |
C7—C24 | 1.533 (6) | C26—H26 | 0.93 |
C7—C8 | 1.536 (6) | C27—H27A | 0.96 |
C7—C25 | 1.537 (7) | C27—H27B | 0.96 |
C8—C9 | 1.510 (6) | C27—H27C | 0.96 |
C8—H8A | 0.97 | C28—H28A | 0.96 |
C8—H8B | 0.97 | C28—H28B | 0.96 |
C10—C11 | 1.462 (6) | C28—H28C | 0.96 |
C1—N1—C12 | 120.0 (3) | C14—C13—H13 | 120.6 |
C1—N1—C9 | 116.9 (3) | C12—C13—H13 | 120.6 |
C12—N1—C9 | 123.0 (3) | C13—C14—C15 | 121.9 (5) |
C10—N2—C1 | 125.9 (4) | C13—C14—H14 | 119.1 |
C10—N2—H2 | 117.0 | C15—C14—H14 | 119.1 |
C1—N2—H2 | 117.0 | C16—C15—C14 | 118.9 (4) |
C26—N4—C27 | 120.6 (9) | C16—C15—H15 | 120.5 |
C26—N4—C28 | 122.0 (9) | C14—C15—H15 | 120.5 |
C27—N4—C28 | 117.3 (8) | C15—C16—C11 | 121.1 (5) |
C2—C1—N2 | 123.9 (4) | C15—C16—H16 | 119.5 |
C2—C1—N1 | 120.3 (4) | C11—C16—H16 | 119.5 |
N2—C1—N1 | 115.8 (3) | N3—C17—C2 | 173.8 (5) |
C1—C2—C17 | 121.7 (4) | C23—C18—C19 | 117.0 (4) |
C1—C2—C3 | 121.3 (4) | C23—C18—C3 | 122.8 (4) |
C17—C2—C3 | 117.0 (4) | C19—C18—C3 | 120.1 (4) |
C4—C3—C18 | 115.7 (3) | C20—C19—C18 | 122.3 (4) |
C4—C3—C2 | 107.7 (3) | C20—C19—H19 | 118.9 |
C18—C3—C2 | 111.7 (3) | C18—C19—H19 | 118.9 |
C4—C3—H3 | 107.1 | C19—C20—C21 | 118.7 (4) |
C18—C3—H3 | 107.1 | C19—C20—H20 | 120.6 |
C2—C3—H3 | 107.1 | C21—C20—H20 | 120.6 |
C9—C4—C5 | 120.2 (4) | C20—C21—C22 | 121.1 (4) |
C9—C4—C3 | 122.6 (4) | C20—C21—Cl1 | 119.4 (3) |
C5—C4—C3 | 117.0 (3) | C22—C21—Cl1 | 119.5 (4) |
O1—C5—C4 | 119.2 (4) | C23—C22—C21 | 118.8 (4) |
O1—C5—C6 | 122.9 (4) | C23—C22—H22 | 120.6 |
C4—C5—C6 | 117.9 (4) | C21—C22—H22 | 120.6 |
C5—C6—C7 | 113.8 (4) | C22—C23—C18 | 122.1 (4) |
C5—C6—H6A | 108.8 | C22—C23—H23 | 118.9 |
C7—C6—H6A | 108.8 | C18—C23—H23 | 118.9 |
C5—C6—H6B | 108.8 | C7—C24—H24A | 109.5 |
C7—C6—H6B | 108.8 | C7—C24—H24B | 109.5 |
H6A—C6—H6B | 107.7 | H24A—C24—H24B | 109.5 |
C6—C7—C24 | 110.0 (4) | C7—C24—H24C | 109.5 |
C6—C7—C8 | 107.1 (4) | H24A—C24—H24C | 109.5 |
C24—C7—C8 | 108.7 (4) | H24B—C24—H24C | 109.5 |
C6—C7—C25 | 111.5 (4) | C7—C25—H25A | 109.5 |
C24—C7—C25 | 108.5 (4) | C7—C25—H25B | 109.5 |
C8—C7—C25 | 111.0 (4) | H25A—C25—H25B | 109.5 |
C9—C8—C7 | 111.7 (3) | C7—C25—H25C | 109.5 |
C9—C8—H8A | 109.3 | H25A—C25—H25C | 109.5 |
C7—C8—H8A | 109.3 | H25B—C25—H25C | 109.5 |
C9—C8—H8B | 109.3 | O3—C26—N4 | 124.8 (10) |
C7—C8—H8B | 109.3 | O3—C26—H26 | 117.6 |
H8A—C8—H8B | 107.9 | N4—C26—H26 | 117.6 |
C4—C9—N1 | 119.3 (4) | N4—C27—H27A | 109.5 |
C4—C9—C8 | 121.6 (4) | N4—C27—H27B | 109.5 |
N1—C9—C8 | 118.5 (3) | H27A—C27—H27B | 109.5 |
O2—C10—N2 | 121.7 (4) | N4—C27—H27C | 109.5 |
O2—C10—C11 | 122.3 (4) | H27A—C27—H27C | 109.5 |
N2—C10—C11 | 115.9 (4) | H27B—C27—H27C | 109.5 |
C16—C11—C12 | 119.9 (4) | N4—C28—H28A | 109.5 |
C16—C11—C10 | 120.2 (4) | N4—C28—H28B | 109.5 |
C12—C11—C10 | 119.8 (4) | H28A—C28—H28B | 109.5 |
C11—C12—C13 | 119.4 (4) | N4—C28—H28C | 109.5 |
C11—C12—N1 | 118.6 (4) | H28A—C28—H28C | 109.5 |
C13—C12—N1 | 122.0 (4) | H28B—C28—H28C | 109.5 |
C14—C13—C12 | 118.8 (4) | ||
C10—N2—C1—C2 | 175.0 (4) | C7—C8—C9—N1 | −144.2 (4) |
C10—N2—C1—N1 | −8.0 (6) | C1—N2—C10—O2 | 176.6 (4) |
C12—N1—C1—C2 | −160.9 (4) | C1—N2—C10—C11 | −6.9 (6) |
C9—N1—C1—C2 | 22.9 (5) | O2—C10—C11—C16 | 10.0 (7) |
C12—N1—C1—N2 | 22.0 (5) | N2—C10—C11—C16 | −166.4 (4) |
C9—N1—C1—N2 | −154.3 (3) | O2—C10—C11—C12 | −175.2 (4) |
N2—C1—C2—C17 | 1.7 (7) | N2—C10—C11—C12 | 8.3 (6) |
N1—C1—C2—C17 | −175.2 (4) | C16—C11—C12—C13 | 1.4 (6) |
N2—C1—C2—C3 | −175.5 (4) | C10—C11—C12—C13 | −173.4 (4) |
N1—C1—C2—C3 | 7.6 (6) | C16—C11—C12—N1 | 179.8 (4) |
C1—C2—C3—C4 | −30.2 (5) | C10—C11—C12—N1 | 5.0 (6) |
C17—C2—C3—C4 | 152.5 (4) | C1—N1—C12—C11 | −20.8 (5) |
C1—C2—C3—C18 | 97.9 (5) | C9—N1—C12—C11 | 155.2 (4) |
C17—C2—C3—C18 | −79.5 (5) | C1—N1—C12—C13 | 157.6 (4) |
C18—C3—C4—C9 | −99.9 (5) | C9—N1—C12—C13 | −26.4 (6) |
C2—C3—C4—C9 | 25.8 (5) | C11—C12—C13—C14 | −3.1 (6) |
C18—C3—C4—C5 | 84.3 (5) | N1—C12—C13—C14 | 178.6 (4) |
C2—C3—C4—C5 | −150.0 (4) | C12—C13—C14—C15 | 2.0 (7) |
C9—C4—C5—O1 | 173.9 (4) | C13—C14—C15—C16 | 0.8 (8) |
C3—C4—C5—O1 | −10.1 (6) | C14—C15—C16—C11 | −2.6 (8) |
C9—C4—C5—C6 | −6.7 (6) | C12—C11—C16—C15 | 1.5 (7) |
C3—C4—C5—C6 | 169.3 (4) | C10—C11—C16—C15 | 176.2 (5) |
O1—C5—C6—C7 | 154.3 (4) | C4—C3—C18—C23 | 57.6 (5) |
C4—C5—C6—C7 | −25.1 (6) | C2—C3—C18—C23 | −66.1 (5) |
C5—C6—C7—C24 | 173.0 (4) | C4—C3—C18—C19 | −125.7 (4) |
C5—C6—C7—C8 | 55.0 (5) | C2—C3—C18—C19 | 110.7 (4) |
C5—C6—C7—C25 | −66.6 (5) | C23—C18—C19—C20 | 1.2 (7) |
C6—C7—C8—C9 | −55.7 (5) | C3—C18—C19—C20 | −175.7 (4) |
C24—C7—C8—C9 | −174.6 (4) | C18—C19—C20—C21 | −0.3 (7) |
C25—C7—C8—C9 | 66.2 (5) | C19—C20—C21—C22 | −0.6 (7) |
C5—C4—C9—N1 | 176.8 (4) | C19—C20—C21—Cl1 | 178.3 (4) |
C3—C4—C9—N1 | 1.1 (6) | C20—C21—C22—C23 | 0.5 (7) |
C5—C4—C9—C8 | 5.0 (6) | Cl1—C21—C22—C23 | −178.3 (4) |
C3—C4—C9—C8 | −170.6 (4) | C21—C22—C23—C18 | 0.5 (7) |
C1—N1—C9—C4 | −27.3 (5) | C19—C18—C23—C22 | −1.3 (7) |
C12—N1—C9—C4 | 156.5 (4) | C3—C18—C23—C22 | 175.6 (4) |
C1—N1—C9—C8 | 144.7 (4) | C27—N4—C26—O3 | −179.7 (9) |
C12—N1—C9—C8 | −31.4 (5) | C28—N4—C26—O3 | 3.3 (15) |
C7—C8—C9—C4 | 27.6 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.04 | 2.849 (5) | 157 |
C20—H20···O1ii | 0.93 | 2.38 | 3.269 (6) | 160 |
C13—H13···Cg1iii | 0.93 | 2.84 | 3.530 (5) | 132 |
C26—H26···Cg2iv | 0.93 | 2.96 | 3.720 (10) | 140 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1/2, y+3/2, −z+1/2; (iv) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C25H20ClN3O2·C3H7NO |
Mr | 502.99 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 36.340 (15), 11.780 (5), 11.870 (5) |
β (°) | 102.714 (5) |
V (Å3) | 4957 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.23 × 0.14 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.957, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12316, 4326, 2288 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.216, 1.02 |
No. of reflections | 4326 |
No. of parameters | 325 |
No. of restraints | 60 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.42 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.04 | 2.849 (5) | 157 |
C20—H20···O1ii | 0.93 | 2.38 | 3.269 (6) | 160 |
C13—H13···Cg1iii | 0.93 | 2.84 | 3.530 (5) | 132 |
C26—H26···Cg2iv | 0.93 | 2.96 | 3.720 (10) | 140 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1/2, y+3/2, −z+1/2; (iv) x, y−1, z. |
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The pyrido[1,2-a]pyrimidine core has been a successful motif for the development of biologically interesting molecules. Compounds containing the pyrido[1,2-a]pyrimidine ring system have been used as analgesics (Hermecz & Meszaros, 1988), antiallergics (Doria et al., 1983), antiasthmatics, antipsychotics (Colpaert, 2003), gastrointestinal protective (Knoll et al., 1987), neurotropic and stress-protecting agents (Kozlovskaya et al., 1995). Moreover, some examples are key intermediates for the synthesis of rutaecarpine alkaloids and several are neutral hydrogen chloride acceptors in organic synthesis (Hermecz et al., 1996). The discovery of quinolino[1,2-a]quinazoline including imidazo[1,2-a]pyridine moiety as new potential pharmacological molecules may be of great significance. We report herein the crystal structure of the title compound.
The asymmetric unit of the title compound (Fig. 1) contains one C25H20ClN3O2 molecule and one C3H7NO molecule. In the main molecule, the dihydropyridine ring adopts a boat conformation, with the atoms C3 and N1 deviating from the C1/C2/C9/C4 plane by 0.356 (6) and 0.272 (5) Å, respectively. The pyrimidine ring adopts a flattened boat conformation, with the atoms C10 and N1 deviating from the C1/N2/C12/C11 plane by 0.084 (6) and 0.223 (5) Å, respectively. The cyclohexene ring adopts an envelop conformation, with the atom C7 deviating from the C4/C5/C6/C8/C9 plane by 0.709 (6) Å. The dihedral angle between the C1/C2/C9/C4 and C18—C23 planes is 85.2 (2)°, and that between the C1/N2/C12/C11 and C11—C16 planes is 9.5 (1)°.
In the crystal structure, the main molecules exist as N—H···O hydrogen-bonded dimers. The crystal packing is further stabilized by C—H···O and C—H···π interactions (Table 1). The N,N-dimethylformamide molecules lie within a channel formed by the C25H20ClN3O2 molecules (Fig.2).