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The single-crystal X-ray diffraction study of the title molecule [alternative name: N(2)-acetyl-1,3-diphenyl-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine], C26H22N2O, confirms that it is a 1,6-naphthyridine derivative whose structural characterization was not possible from 1H, 13C NMR and mass spectral data. The tetrahydro-1,6-napthyridine ring has a boat conformation. The equatorial and axial orientations of the two phenyl groups and the coplanarity of the acetyl group with the tetrahydronaphthyridine ring are also confirmed.
Supporting information
CCDC reference: 170766
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.055
- wR factor = 0.167
- Data-to-parameter ratio = 16.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
WEIGH_01 Alert C Extra text has been found in the
_refine_ls_weighting_scheme field. This should be in the
_refine_ls_weighting_details field.
Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0804P)^2^] wher
Weighting scheme identified as calc
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
The title compound was obtained by the acetylation of the corresponding amine
with acetic anhydride and triethylamine in benzene under reflux conditions.
Diffraction quality crystals were obtained by recrystallizing the crude
product from a benzene–petroleum ether mixture. The parent amine itself was
obtained by the action of sodium azide with
2,4,6,8-tetraphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one (Sivakumar, 2000), as a
non-crystalline product.
The asymmetric unit of the cell consists of two independent molecules with a
total of 58 non-H atoms. All the H atoms were included in calculated
positions. While the C—H distances were refined by a riding model, the
displacement parameters of the H atoms were tied to common values.
Data collection: P3/P4 (Siemens, 1989); cell refinement: P3/P4; data reduction: P3/P4 and XDISK (Siemens, 1989); program(s) used to solve structure: SIR97 (Altomare et al., 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, 1983).
N(2)-Acetyl-1,3-diphenyl-1,2,3,4-tetrahydrobenzo[
b]-1,6-naphthyridine
top
Crystal data top
C26H22N2O | Z = 4 |
Mr = 378.46 | F(000) = 800 |
Triclinic, P1 | Dx = 1.239 Mg m−3 |
a = 10.394 (2) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 10.493 (3) Å | Cell parameters from 40 reflections |
c = 20.265 (4) Å | θ = 10–30° |
α = 76.03 (2)° | µ = 0.08 mm−1 |
β = 79.83 (2)° | T = 293 K |
γ = 72.21 (2)° | Rectangular block, colorless |
V = 2029.6 (8) Å3 | 0.05 × 0.05 × 0.04 mm |
Data collection top
Siemens P3 diffractometer | Rint = 0.023 |
Radiation source: fine-focus sealed tube | θmax = 27.7°, θmin = 2.1° |
Graphite monochromator | h = 0→13 |
ω–2θ scans | k = −13→13 |
9786 measured reflections | l = −25→26 |
9279 independent reflections | 3 standard reflections every 300 reflections |
4446 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.167 | Calculated w = 1/[σ2(Fo2) + (0.0804P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
9279 reflections | Δρmax = 0.35 e Å−3 |
566 parameters | Δρmin = −0.38 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0238 (18) |
Crystal data top
C26H22N2O | γ = 72.21 (2)° |
Mr = 378.46 | V = 2029.6 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.394 (2) Å | Mo Kα radiation |
b = 10.493 (3) Å | µ = 0.08 mm−1 |
c = 20.265 (4) Å | T = 293 K |
α = 76.03 (2)° | 0.05 × 0.05 × 0.04 mm |
β = 79.83 (2)° | |
Data collection top
Siemens P3 diffractometer | Rint = 0.023 |
9786 measured reflections | 3 standard reflections every 300 reflections |
9279 independent reflections | intensity decay: none |
4446 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.35 e Å−3 |
9279 reflections | Δρmin = −0.38 e Å−3 |
566 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 | x | y | z | Uiso*/Ueq | |
N1 | 0.2866 (2) | 0.2928 (2) | 0.87272 (10) | 0.0527 (5) | |
C2 | 0.1617 (3) | 0.3530 (2) | 0.84974 (11) | 0.0504 (6) | |
C3 | 0.0925 (2) | 0.2839 (2) | 0.82231 (11) | 0.0504 (6) | |
C4 | 0.1571 (3) | 0.1458 (2) | 0.81954 (12) | 0.0494 (6) | |
H4 | 0.1144 (13) | 0.0948 (15) | 0.8008 (6) | 0.0751 (14)* | |
C5 | 0.3545 (2) | −0.0612 (2) | 0.84244 (12) | 0.0477 (6) | |
H5 | 0.3206 (10) | −0.0852 (7) | 0.8066 (10) | 0.0751 (14)* | |
N6 | 0.50087 (19) | −0.07346 (19) | 0.82033 (9) | 0.0480 (5) | |
C7 | 0.5725 (2) | 0.0041 (2) | 0.84586 (12) | 0.0482 (6) | |
H7 | 0.6033 (9) | 0.0663 (19) | 0.8066 (12) | 0.0751 (14)* | |
C8 | 0.4752 (2) | 0.0910 (2) | 0.89515 (13) | 0.0525 (6) | |
H8A | 0.4609 (3) | 0.0304 (11) | 0.9407 (8) | 0.0751 (14)* | |
H8B | 0.5181 (8) | 0.1596 (12) | 0.90203 (19) | 0.0751 (14)* | |
C9 | 0.1002 (3) | 0.4916 (3) | 0.85329 (14) | 0.0636 (7) | |
H9 | 0.1458 (14) | 0.5407 (15) | 0.8727 (6) | 0.0751 (14)* | |
C10 | −0.0223 (3) | 0.5564 (3) | 0.82981 (14) | 0.0707 (8) | |
H10 | −0.0636 (13) | 0.651 (3) | 0.83219 (16) | 0.0751 (14)* | |
C11 | −0.0895 (3) | 0.4880 (3) | 0.80218 (15) | 0.0685 (8) | |
H11 | −0.178 (3) | 0.5375 (14) | 0.7854 (5) | 0.0751 (14)* | |
C12 | −0.0342 (3) | 0.3545 (3) | 0.79808 (13) | 0.0599 (7) | |
H12 | −0.0814 (14) | 0.3085 (14) | 0.7787 (6) | 0.0751 (14)* | |
C13 | 0.2793 (2) | 0.0853 (2) | 0.84331 (11) | 0.0460 (6) | |
C14 | 0.3408 (2) | 0.1640 (2) | 0.86932 (11) | 0.0481 (6) | |
C15 | 0.5576 (3) | −0.1361 (2) | 0.76624 (12) | 0.0520 (6) | |
C16 | 0.6991 (3) | −0.1318 (3) | 0.73460 (13) | 0.0644 (8) | |
H16A | 0.7611 (12) | −0.174 (2) | 0.7682 (7) | 0.120 (5)* | |
H16B | 0.7008 (6) | −0.0390 (16) | 0.7180 (10) | 0.120 (5)* | |
H16C | 0.7250 (10) | −0.179 (2) | 0.6975 (9) | 0.120 (5)* | |
O17 | 0.4949 (2) | −0.19456 (19) | 0.74316 (9) | 0.0682 (5) | |
C18 | 0.3291 (2) | −0.1627 (2) | 0.90780 (13) | 0.0508 (6) | |
C19 | 0.3726 (3) | −0.3005 (3) | 0.90644 (17) | 0.0737 (8) | |
H19 | 0.4198 (14) | −0.3291 (9) | 0.8654 (12) | 0.0751 (14)* | |
C20 | 0.3493 (4) | −0.3976 (3) | 0.9630 (2) | 0.0884 (11) | |
H20 | 0.3788 (10) | −0.489 (3) | 0.9607 (2) | 0.0751 (14)* | |
C21 | 0.2834 (4) | −0.3588 (4) | 1.0218 (2) | 0.0876 (11) | |
H21 | 0.2683 (6) | −0.423 (2) | 1.0595 (13) | 0.0751 (14)* | |
C22 | 0.2396 (4) | −0.2238 (4) | 1.02477 (17) | 0.0838 (10) | |
H22 | 0.1952 (15) | −0.1975 (9) | 1.0645 (13) | 0.0751 (14)* | |
C23 | 0.2621 (3) | −0.1261 (3) | 0.96777 (14) | 0.0662 (8) | |
H23 | 0.2309 (10) | −0.033 (3) | 0.97032 (16) | 0.0751 (14)* | |
C24 | 0.6952 (2) | −0.0828 (2) | 0.88142 (12) | 0.0484 (6) | |
C25 | 0.8124 (3) | −0.0404 (3) | 0.86945 (15) | 0.0639 (7) | |
H25 | 0.8178 (3) | 0.040 (2) | 0.8355 (10) | 0.0751 (14)* | |
C26 | 0.9216 (3) | −0.1128 (4) | 0.90581 (18) | 0.0788 (9) | |
H26 | 0.998 (2) | −0.0835 (10) | 0.8979 (3) | 0.0751 (14)* | |
C27 | 0.9158 (3) | −0.2281 (3) | 0.95365 (17) | 0.0750 (9) | |
H27 | 0.997 (2) | −0.2813 (16) | 0.9806 (8) | 0.0751 (14)* | |
C28 | 0.8002 (3) | −0.2721 (3) | 0.96529 (14) | 0.0673 (8) | |
H28 | 0.7964 (3) | −0.354 (2) | 0.9986 (10) | 0.0751 (14)* | |
C29 | 0.6904 (3) | −0.2001 (3) | 0.92976 (13) | 0.0583 (7) | |
H29 | 0.609 (2) | −0.2317 (10) | 0.9387 (3) | 0.0751 (14)* | |
N1A | 0.5157 (2) | 0.1691 (2) | 0.65608 (10) | 0.0500 (5) | |
C2A | 0.5050 (3) | 0.2768 (2) | 0.68556 (12) | 0.0490 (6) | |
C3A | 0.3821 (3) | 0.3787 (2) | 0.69328 (12) | 0.0507 (6) | |
C4A | 0.2676 (3) | 0.3667 (2) | 0.66891 (12) | 0.0515 (6) | |
H4A | 0.183 (3) | 0.432 (2) | 0.67391 (19) | 0.0751 (14)* | |
C5A | 0.1633 (2) | 0.2383 (2) | 0.61174 (12) | 0.0497 (6) | |
H5A | 0.082 (2) | 0.2850 (14) | 0.6353 (7) | 0.0751 (14)* | |
N6A | 0.16922 (19) | 0.09069 (19) | 0.63110 (9) | 0.0480 (5) | |
C7A | 0.3002 (2) | −0.0130 (2) | 0.62050 (13) | 0.0475 (6) | |
H7A | 0.3194 (6) | −0.0743 (17) | 0.6666 (13) | 0.0751 (14)* | |
C8A | 0.4171 (2) | 0.0541 (2) | 0.59562 (13) | 0.0515 (6) | |
H8A1 | 0.5031 (16) | −0.0152 (13) | 0.60223 (16) | 0.0751 (14)* | |
H8A2 | 0.4164 (2) | 0.0922 (7) | 0.5469 (9) | 0.0751 (14)* | |
C9A | 0.6222 (3) | 0.2863 (3) | 0.70794 (14) | 0.0629 (7) | |
H9A | 0.714 (2) | 0.212 (2) | 0.7021 (2) | 0.0751 (14)* | |
C10A | 0.6150 (4) | 0.3924 (3) | 0.73710 (17) | 0.0784 (9) | |
H10A | 0.695 (3) | 0.3979 (4) | 0.7524 (5) | 0.0751 (14)* | |
C11A | 0.4942 (4) | 0.4926 (4) | 0.74516 (16) | 0.0788 (10) | |
H11A | 0.4914 (4) | 0.565 (2) | 0.7653 (6) | 0.0751 (14)* | |
C12A | 0.3796 (3) | 0.4864 (3) | 0.72392 (14) | 0.0677 (8) | |
H12A | 0.296 (2) | 0.556 (2) | 0.7299 (2) | 0.0751 (14)* | |
C13A | 0.2795 (2) | 0.2611 (2) | 0.63834 (11) | 0.0466 (6) | |
C14A | 0.4073 (2) | 0.1644 (2) | 0.63236 (12) | 0.0465 (6) | |
C15A | 0.0602 (3) | 0.0544 (3) | 0.67013 (13) | 0.0589 (7) | |
C16A | 0.0707 (3) | −0.0945 (3) | 0.69625 (17) | 0.0817 (10) | |
H16D | −0.0069 (18) | −0.1041 (4) | 0.7257 (11) | 0.120 (5)* | |
H16E | 0.1471 (19) | −0.1354 (10) | 0.7198 (11) | 0.120 (5)* | |
H16F | 0.079 (2) | −0.1363 (10) | 0.6595 (7) | 0.120 (5)* | |
O17A | −0.04550 (19) | 0.1394 (2) | 0.68440 (11) | 0.0804 (6) | |
C18A | 0.1524 (2) | 0.2950 (2) | 0.53592 (12) | 0.0516 (6) | |
C19A | 0.2509 (3) | 0.3453 (3) | 0.49173 (14) | 0.0696 (8) | |
H19A | 0.329 (2) | 0.3452 (3) | 0.5081 (5) | 0.0751 (14)* | |
C20A | 0.2339 (4) | 0.3954 (4) | 0.42356 (16) | 0.0869 (10) | |
H20A | 0.302 (2) | 0.4293 (11) | 0.3935 (9) | 0.0751 (14)* | |
C21A | 0.1192 (4) | 0.3970 (3) | 0.39869 (17) | 0.0874 (11) | |
H21A | 0.1086 (5) | 0.4308 (11) | 0.3515 (15) | 0.0751 (14)* | |
C22A | 0.0198 (4) | 0.3498 (3) | 0.44211 (16) | 0.0810 (10) | |
H22A | −0.061 (2) | 0.3517 (3) | 0.4251 (5) | 0.0751 (14)* | |
C23A | 0.0356 (3) | 0.2996 (3) | 0.51003 (15) | 0.0678 (8) | |
H23A | −0.036 (2) | 0.2669 (10) | 0.5404 (9) | 0.0751 (14)* | |
C24A | 0.2994 (2) | −0.1035 (2) | 0.57260 (12) | 0.0486 (6) | |
C25A | 0.2334 (3) | −0.0564 (3) | 0.51458 (14) | 0.0624 (7) | |
H25A | 0.1815 (15) | 0.038 (3) | 0.5037 (3) | 0.0751 (14)* | |
C26A | 0.2405 (3) | −0.1431 (4) | 0.47193 (17) | 0.0750 (9) | |
H26A | 0.1959 (15) | −0.1095 (12) | 0.4325 (13) | 0.0751 (14)* | |
C27A | 0.3118 (3) | −0.2767 (4) | 0.48640 (17) | 0.0747 (9) | |
H27A | 0.3150 (3) | −0.3341 (19) | 0.4581 (9) | 0.0751 (14)* | |
C28A | 0.3787 (3) | −0.3248 (3) | 0.54367 (17) | 0.0737 (9) | |
H28A | 0.4304 (15) | −0.420 (3) | 0.5541 (4) | 0.0751 (14)* | |
C29A | 0.3727 (3) | −0.2386 (3) | 0.58650 (15) | 0.0614 (7) | |
H29A | 0.4226 (14) | −0.2749 (11) | 0.6284 (12) | 0.0751 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0600 (13) | 0.0450 (12) | 0.0505 (12) | −0.0050 (10) | −0.0095 (10) | −0.0147 (9) |
C2 | 0.0565 (15) | 0.0475 (14) | 0.0415 (13) | −0.0067 (12) | −0.0053 (11) | −0.0080 (11) |
C3 | 0.0529 (15) | 0.0528 (15) | 0.0399 (13) | −0.0097 (12) | −0.0046 (11) | −0.0054 (11) |
C4 | 0.0531 (15) | 0.0484 (14) | 0.0467 (13) | −0.0130 (12) | −0.0067 (11) | −0.0102 (11) |
C5 | 0.0499 (15) | 0.0462 (14) | 0.0497 (14) | −0.0117 (11) | −0.0122 (11) | −0.0116 (11) |
N6 | 0.0517 (12) | 0.0469 (11) | 0.0450 (11) | −0.0100 (9) | −0.0082 (9) | −0.0112 (9) |
C7 | 0.0540 (15) | 0.0468 (14) | 0.0449 (13) | −0.0139 (12) | −0.0093 (11) | −0.0082 (11) |
C8 | 0.0541 (15) | 0.0501 (14) | 0.0574 (15) | −0.0094 (12) | −0.0155 (12) | −0.0181 (12) |
C9 | 0.0715 (19) | 0.0533 (16) | 0.0628 (17) | −0.0044 (15) | −0.0153 (14) | −0.0163 (13) |
C10 | 0.082 (2) | 0.0515 (16) | 0.0681 (18) | 0.0054 (16) | −0.0175 (16) | −0.0162 (14) |
C11 | 0.0593 (17) | 0.0651 (19) | 0.0676 (18) | 0.0050 (15) | −0.0146 (14) | −0.0110 (14) |
C12 | 0.0558 (16) | 0.0610 (17) | 0.0568 (16) | −0.0048 (14) | −0.0120 (13) | −0.0109 (13) |
C13 | 0.0504 (14) | 0.0444 (13) | 0.0405 (12) | −0.0092 (11) | −0.0063 (11) | −0.0073 (10) |
C14 | 0.0545 (15) | 0.0478 (14) | 0.0409 (12) | −0.0112 (12) | −0.0067 (11) | −0.0098 (11) |
C15 | 0.0647 (17) | 0.0417 (13) | 0.0437 (13) | −0.0044 (12) | −0.0103 (12) | −0.0077 (11) |
C16 | 0.0642 (18) | 0.0620 (17) | 0.0565 (16) | −0.0015 (14) | −0.0018 (13) | −0.0164 (13) |
O17 | 0.0843 (14) | 0.0608 (12) | 0.0652 (12) | −0.0144 (10) | −0.0125 (10) | −0.0272 (9) |
C18 | 0.0492 (14) | 0.0496 (15) | 0.0549 (15) | −0.0149 (12) | −0.0100 (12) | −0.0080 (12) |
C19 | 0.087 (2) | 0.0518 (17) | 0.078 (2) | −0.0177 (15) | 0.0027 (16) | −0.0137 (15) |
C20 | 0.097 (3) | 0.0479 (18) | 0.108 (3) | −0.0184 (17) | −0.004 (2) | 0.0005 (18) |
C21 | 0.101 (3) | 0.075 (2) | 0.079 (2) | −0.037 (2) | −0.014 (2) | 0.0195 (19) |
C22 | 0.103 (3) | 0.087 (3) | 0.0584 (18) | −0.035 (2) | 0.0058 (17) | −0.0065 (17) |
C23 | 0.078 (2) | 0.0606 (17) | 0.0609 (17) | −0.0219 (15) | −0.0038 (15) | −0.0121 (14) |
C24 | 0.0496 (14) | 0.0522 (14) | 0.0434 (13) | −0.0109 (12) | −0.0059 (11) | −0.0128 (11) |
C25 | 0.0559 (17) | 0.0673 (18) | 0.0699 (18) | −0.0215 (14) | −0.0085 (14) | −0.0094 (14) |
C26 | 0.0537 (18) | 0.097 (3) | 0.094 (2) | −0.0221 (18) | −0.0144 (17) | −0.028 (2) |
C27 | 0.064 (2) | 0.082 (2) | 0.075 (2) | 0.0002 (17) | −0.0263 (17) | −0.0233 (18) |
C28 | 0.073 (2) | 0.0676 (18) | 0.0521 (16) | −0.0062 (16) | −0.0142 (14) | −0.0066 (13) |
C29 | 0.0565 (16) | 0.0627 (17) | 0.0526 (15) | −0.0148 (14) | −0.0079 (12) | −0.0066 (13) |
N1A | 0.0461 (12) | 0.0501 (12) | 0.0540 (12) | −0.0146 (10) | −0.0071 (9) | −0.0078 (10) |
C2A | 0.0549 (15) | 0.0467 (14) | 0.0448 (13) | −0.0191 (12) | −0.0067 (11) | −0.0009 (11) |
C3A | 0.0649 (17) | 0.0457 (14) | 0.0422 (13) | −0.0202 (13) | −0.0057 (11) | −0.0039 (11) |
C4A | 0.0524 (15) | 0.0465 (14) | 0.0478 (14) | −0.0088 (12) | −0.0007 (11) | −0.0046 (11) |
C5A | 0.0406 (13) | 0.0544 (15) | 0.0501 (14) | −0.0070 (11) | −0.0042 (11) | −0.0113 (11) |
N6A | 0.0395 (11) | 0.0534 (12) | 0.0478 (11) | −0.0123 (9) | 0.0000 (9) | −0.0078 (9) |
C7A | 0.0404 (13) | 0.0510 (14) | 0.0483 (13) | −0.0099 (11) | −0.0040 (10) | −0.0091 (11) |
C8A | 0.0405 (13) | 0.0565 (15) | 0.0573 (15) | −0.0101 (12) | −0.0007 (11) | −0.0183 (12) |
C9A | 0.0650 (18) | 0.0588 (17) | 0.0688 (18) | −0.0262 (15) | −0.0179 (14) | −0.0008 (14) |
C10A | 0.088 (2) | 0.074 (2) | 0.089 (2) | −0.040 (2) | −0.0306 (19) | −0.0095 (17) |
C11A | 0.113 (3) | 0.068 (2) | 0.074 (2) | −0.043 (2) | −0.0177 (19) | −0.0188 (16) |
C12A | 0.087 (2) | 0.0552 (17) | 0.0620 (17) | −0.0242 (16) | −0.0025 (15) | −0.0123 (13) |
C13A | 0.0443 (14) | 0.0474 (14) | 0.0436 (13) | −0.0101 (11) | −0.0017 (10) | −0.0061 (11) |
C14A | 0.0411 (13) | 0.0516 (14) | 0.0452 (13) | −0.0140 (11) | −0.0027 (10) | −0.0067 (11) |
C15A | 0.0507 (16) | 0.0727 (18) | 0.0552 (15) | −0.0218 (14) | 0.0020 (12) | −0.0160 (14) |
C16A | 0.081 (2) | 0.081 (2) | 0.083 (2) | −0.0400 (18) | 0.0212 (17) | −0.0144 (17) |
O17A | 0.0478 (11) | 0.0870 (15) | 0.0991 (15) | −0.0178 (11) | 0.0174 (10) | −0.0244 (12) |
C18A | 0.0458 (14) | 0.0498 (14) | 0.0539 (14) | −0.0050 (12) | −0.0100 (12) | −0.0079 (11) |
C19A | 0.0600 (17) | 0.084 (2) | 0.0565 (17) | −0.0180 (16) | −0.0074 (14) | −0.0012 (15) |
C20A | 0.081 (2) | 0.106 (3) | 0.0562 (18) | −0.021 (2) | −0.0007 (17) | 0.0056 (17) |
C21A | 0.096 (3) | 0.095 (3) | 0.0508 (18) | −0.001 (2) | −0.0209 (18) | 0.0006 (16) |
C22A | 0.075 (2) | 0.092 (2) | 0.071 (2) | −0.0129 (18) | −0.0342 (18) | −0.0031 (18) |
C23A | 0.0562 (17) | 0.0727 (19) | 0.0672 (18) | −0.0102 (14) | −0.0181 (14) | −0.0021 (14) |
C24A | 0.0435 (13) | 0.0545 (15) | 0.0499 (14) | −0.0179 (12) | 0.0007 (11) | −0.0129 (11) |
C25A | 0.0666 (18) | 0.0626 (17) | 0.0612 (17) | −0.0180 (14) | −0.0111 (14) | −0.0152 (14) |
C26A | 0.082 (2) | 0.090 (2) | 0.0674 (19) | −0.0320 (19) | −0.0125 (16) | −0.0273 (17) |
C27A | 0.085 (2) | 0.082 (2) | 0.073 (2) | −0.042 (2) | 0.0167 (18) | −0.0386 (18) |
C28A | 0.077 (2) | 0.0591 (18) | 0.084 (2) | −0.0207 (16) | 0.0090 (17) | −0.0231 (16) |
C29A | 0.0605 (17) | 0.0556 (17) | 0.0647 (17) | −0.0128 (14) | −0.0017 (13) | −0.0135 (13) |
Geometric parameters (Å, º) top
N1—C14 | 1.309 (3) | N1A—C14A | 1.319 (3) |
N1—C2 | 1.368 (3) | N1A—C2A | 1.368 (3) |
C2—C9 | 1.412 (3) | C2A—C3A | 1.405 (3) |
C2—C3 | 1.417 (3) | C2A—C9A | 1.411 (3) |
C3—C12 | 1.407 (3) | C3A—C12A | 1.407 (3) |
C3—C4 | 1.410 (3) | C3A—C4A | 1.416 (3) |
C4—C13 | 1.351 (3) | C4A—C13A | 1.359 (3) |
C4—H4 | 0.9639 | C4A—H4A | 0.9442 |
C5—N6 | 1.483 (3) | C5A—N6A | 1.487 (3) |
C5—C13 | 1.499 (3) | C5A—C13A | 1.509 (3) |
C5—C18 | 1.525 (3) | C5A—C18A | 1.519 (3) |
C5—H5 | 0.9743 | C5A—H5A | 0.9450 |
N6—C15 | 1.365 (3) | N6A—C15A | 1.362 (3) |
N6—C7 | 1.481 (3) | N6A—C7A | 1.479 (3) |
C7—C24 | 1.508 (3) | C7A—C24A | 1.516 (3) |
C7—C8 | 1.540 (3) | C7A—C8A | 1.537 (3) |
C7—H7 | 0.9743 | C7A—H7A | 1.0112 |
C8—C14 | 1.491 (3) | C8A—C14A | 1.490 (3) |
C8—H8A | 1.0016 | C8A—H8A1 | 0.9716 |
C8—H8B | 1.0016 | C8A—H8A2 | 0.9716 |
C9—C10 | 1.355 (4) | C9A—C10A | 1.358 (4) |
C9—H9 | 0.9785 | C9A—H9A | 1.0419 |
C10—C11 | 1.398 (4) | C10A—C11A | 1.382 (4) |
C10—H10 | 0.9644 | C10A—H10A | 0.9602 |
C11—C12 | 1.359 (4) | C11A—C12A | 1.360 (4) |
C11—H11 | 0.9867 | C11A—H11A | 0.9344 |
C12—H12 | 0.9662 | C12A—H12A | 0.9584 |
C13—C14 | 1.421 (3) | C13A—C14A | 1.410 (3) |
C15—O17 | 1.229 (3) | C15A—O17A | 1.225 (3) |
C15—C16 | 1.507 (4) | C15A—C16A | 1.500 (4) |
C16—H16A | 0.9546 | C16A—H16D | 0.9315 |
C16—H16B | 0.9546 | C16A—H16E | 0.9315 |
C16—H16C | 0.9546 | C16A—H16F | 0.9315 |
C18—C23 | 1.369 (4) | C18A—C19A | 1.381 (4) |
C18—C19 | 1.383 (4) | C18A—C23A | 1.388 (3) |
C19—C20 | 1.377 (4) | C19A—C20A | 1.377 (4) |
C19—H19 | 0.9539 | C19A—H19A | 0.9305 |
C20—C21 | 1.354 (5) | C20A—C21A | 1.368 (5) |
C20—H20 | 0.9283 | C20A—H20A | 0.9490 |
C21—C22 | 1.362 (4) | C21A—C22A | 1.367 (5) |
C21—H21 | 0.9153 | C21A—H21A | 0.9490 |
C22—C23 | 1.385 (4) | C22A—C23A | 1.370 (4) |
C22—H22 | 0.9141 | C22A—H22A | 0.9522 |
C23—H23 | 0.9373 | C23A—H23A | 0.9679 |
C24—C25 | 1.384 (4) | C24A—C25A | 1.377 (3) |
C24—C29 | 1.384 (3) | C24A—C29A | 1.375 (3) |
C25—C26 | 1.380 (4) | C25A—C26A | 1.376 (4) |
C25—H25 | 0.9634 | C25A—H25A | 0.9683 |
C26—C27 | 1.366 (4) | C26A—C27A | 1.358 (4) |
C26—H26 | 0.9106 | C26A—H26A | 0.9340 |
C27—C28 | 1.378 (4) | C27A—C28A | 1.369 (4) |
C27—H27 | 1.0218 | C27A—H27A | 0.9176 |
C28—C29 | 1.376 (4) | C28A—C29A | 1.379 (4) |
C28—H28 | 0.9627 | C28A—H28A | 0.9671 |
C29—H29 | 0.9725 | C29A—H29A | 1.0071 |
| | | |
C14—N1—C2 | 116.5 (2) | C14A—N1A—C2A | 118.2 (2) |
N1—C2—C9 | 117.8 (2) | N1A—C2A—C3A | 122.3 (2) |
N1—C2—C3 | 123.4 (2) | N1A—C2A—C9A | 118.5 (2) |
C9—C2—C3 | 118.8 (2) | C3A—C2A—C9A | 119.2 (2) |
C12—C3—C4 | 123.0 (2) | C2A—C3A—C12A | 118.8 (3) |
C12—C3—C2 | 119.8 (2) | C2A—C3A—C4A | 117.4 (2) |
C4—C3—C2 | 117.2 (2) | C12A—C3A—C4A | 123.8 (3) |
C13—C4—C3 | 119.5 (2) | C13A—C4A—C3A | 120.1 (2) |
C13—C4—H4 | 120.2 | C13A—C4A—H4A | 119.9 |
C3—C4—H4 | 120.2 | C3A—C4A—H4A | 119.9 |
N6—C5—C13 | 109.67 (19) | N6A—C5A—C13A | 109.29 (19) |
N6—C5—C18 | 113.21 (19) | N6A—C5A—C18A | 112.41 (19) |
C13—C5—C18 | 115.2 (2) | C13A—C5A—C18A | 114.8 (2) |
N6—C5—H5 | 106.0 | N6A—C5A—H5A | 106.6 |
C13—C5—H5 | 106.0 | C13A—C5A—H5A | 106.6 |
C18—C5—H5 | 106.0 | C18A—C5A—H5A | 106.6 |
C15—N6—C7 | 121.4 (2) | C15A—N6A—C7A | 120.9 (2) |
C15—N6—C5 | 116.6 (2) | C15A—N6A—C5A | 118.2 (2) |
C7—N6—C5 | 120.71 (18) | C7A—N6A—C5A | 119.67 (18) |
N6—C7—C24 | 114.60 (19) | N6A—C7A—C24A | 113.91 (19) |
N6—C7—C8 | 110.8 (2) | N6A—C7A—C8A | 111.00 (19) |
C24—C7—C8 | 108.30 (19) | C24A—C7A—C8A | 110.13 (19) |
N6—C7—H7 | 107.6 | N6A—C7A—H7A | 107.2 |
C24—C7—H7 | 107.6 | C24A—C7A—H7A | 107.2 |
C8—C7—H7 | 107.6 | C8A—C7A—H7A | 107.2 |
C14—C8—C7 | 112.5 (2) | C14A—C8A—C7A | 112.5 (2) |
C14—C8—H8A | 109.1 | C14A—C8A—H8A1 | 109.1 |
C7—C8—H8A | 109.1 | C7A—C8A—H8A1 | 109.1 |
C14—C8—H8B | 109.1 | C14A—C8A—H8A2 | 109.1 |
C7—C8—H8B | 109.1 | C7A—C8A—H8A2 | 109.1 |
H8A—C8—H8B | 107.8 | H8A1—C8A—H8A2 | 107.8 |
C10—C9—C2 | 119.9 (3) | C10A—C9A—C2A | 119.9 (3) |
C10—C9—H9 | 120.1 | C10A—C9A—H9A | 120.0 |
C2—C9—H9 | 120.1 | C2A—C9A—H9A | 120.0 |
C9—C10—C11 | 121.0 (3) | C9A—C10A—C11A | 121.1 (3) |
C9—C10—H10 | 119.5 | C9A—C10A—H10A | 119.4 |
C11—C10—H10 | 119.5 | C11A—C10A—H10A | 119.4 |
C12—C11—C10 | 121.0 (3) | C12A—C11A—C10A | 120.3 (3) |
C12—C11—H11 | 119.5 | C12A—C11A—H11A | 119.9 |
C10—C11—H11 | 119.5 | C10A—C11A—H11A | 119.9 |
C11—C12—C3 | 119.4 (3) | C11A—C12A—C3A | 120.6 (3) |
C11—C12—H12 | 120.3 | C11A—C12A—H12A | 119.7 |
C3—C12—H12 | 120.3 | C3A—C12A—H12A | 119.7 |
C4—C13—C14 | 118.8 (2) | C4A—C13A—C14A | 118.4 (2) |
C4—C13—C5 | 122.8 (2) | C4A—C13A—C5A | 124.1 (2) |
C14—C13—C5 | 118.4 (2) | C14A—C13A—C5A | 117.4 (2) |
N1—C14—C13 | 124.6 (2) | N1A—C14A—C13A | 123.6 (2) |
N1—C14—C8 | 119.3 (2) | N1A—C14A—C8A | 119.9 (2) |
C13—C14—C8 | 116.2 (2) | C13A—C14A—C8A | 116.5 (2) |
O17—C15—N6 | 121.1 (2) | O17A—C15A—N6A | 122.1 (3) |
O17—C15—C16 | 120.1 (2) | O17A—C15A—C16A | 119.3 (2) |
N6—C15—C16 | 118.8 (2) | N6A—C15A—C16A | 118.7 (2) |
C15—C16—H16A | 109.5 | C15A—C16A—H16D | 109.5 |
C15—C16—H16B | 109.5 | C15A—C16A—H16E | 109.5 |
H16A—C16—H16B | 109.5 | H16D—C16A—H16E | 109.5 |
C15—C16—H16C | 109.5 | C15A—C16A—H16F | 109.5 |
H16A—C16—H16C | 109.5 | H16D—C16A—H16F | 109.5 |
H16B—C16—H16C | 109.5 | H16E—C16A—H16F | 109.5 |
C23—C18—C19 | 117.4 (3) | C19A—C18A—C23A | 118.3 (3) |
C23—C18—C5 | 124.1 (2) | C19A—C18A—C5A | 123.5 (2) |
C19—C18—C5 | 118.5 (2) | C23A—C18A—C5A | 118.2 (2) |
C18—C19—C20 | 121.6 (3) | C20A—C19A—C18A | 120.3 (3) |
C18—C19—H19 | 119.2 | C20A—C19A—H19A | 119.9 |
C20—C19—H19 | 119.2 | C18A—C19A—H19A | 119.9 |
C21—C20—C19 | 119.9 (3) | C21A—C20A—C19A | 120.7 (3) |
C21—C20—H20 | 120.0 | C21A—C20A—H20A | 119.7 |
C19—C20—H20 | 120.0 | C19A—C20A—H20A | 119.7 |
C20—C21—C22 | 119.9 (3) | C22A—C21A—C20A | 119.7 (3) |
C20—C21—H21 | 120.1 | C22A—C21A—H21A | 120.2 |
C22—C21—H21 | 120.1 | C20A—C21A—H21A | 120.2 |
C21—C22—C23 | 120.2 (3) | C21A—C22A—C23A | 120.2 (3) |
C21—C22—H22 | 119.9 | C21A—C22A—H22A | 119.9 |
C23—C22—H22 | 119.9 | C23A—C22A—H22A | 119.9 |
C18—C23—C22 | 121.1 (3) | C22A—C23A—C18A | 120.9 (3) |
C18—C23—H23 | 119.5 | C22A—C23A—H23A | 119.5 |
C22—C23—H23 | 119.5 | C18A—C23A—H23A | 119.5 |
C25—C24—C29 | 118.8 (2) | C25A—C24A—C29A | 118.3 (2) |
C25—C24—C7 | 119.8 (2) | C25A—C24A—C7A | 123.4 (2) |
C29—C24—C7 | 121.2 (2) | C29A—C24A—C7A | 118.2 (2) |
C26—C25—C24 | 120.5 (3) | C24A—C25A—C26A | 120.5 (3) |
C26—C25—H25 | 119.7 | C24A—C25A—H25A | 119.7 |
C24—C25—H25 | 119.7 | C26A—C25A—H25A | 119.7 |
C27—C26—C25 | 120.4 (3) | C27A—C26A—C25A | 120.8 (3) |
C27—C26—H26 | 119.8 | C27A—C26A—H26A | 119.6 |
C25—C26—H26 | 119.8 | C25A—C26A—H26A | 119.6 |
C26—C27—C28 | 119.6 (3) | C26A—C27A—C28A | 119.3 (3) |
C26—C27—H27 | 120.2 | C26A—C27A—H27A | 120.3 |
C28—C27—H27 | 120.2 | C28A—C27A—H27A | 120.3 |
C27—C28—C29 | 120.6 (3) | C27A—C28A—C29A | 120.2 (3) |
C27—C28—H28 | 119.7 | C27A—C28A—H28A | 119.9 |
C29—C28—H28 | 119.7 | C29A—C28A—H28A | 119.9 |
C28—C29—C24 | 120.2 (3) | C24A—C29A—C28A | 120.7 (3) |
C28—C29—H29 | 119.9 | C24A—C29A—H29A | 119.6 |
C24—C29—H29 | 119.9 | C28A—C29A—H29A | 119.6 |
| | | |
C14—N1—C2—C9 | 179.5 (2) | C14A—N1A—C2A—C3A | 2.2 (3) |
C14—N1—C2—C3 | −1.0 (3) | C14A—N1A—C2A—C9A | −176.8 (2) |
N1—C2—C3—C12 | −178.3 (2) | N1A—C2A—C3A—C12A | −179.8 (2) |
C9—C2—C3—C12 | 1.2 (3) | C9A—C2A—C3A—C12A | −0.7 (3) |
N1—C2—C3—C4 | 0.5 (3) | N1A—C2A—C3A—C4A | −0.3 (3) |
C9—C2—C3—C4 | 180.0 (2) | C9A—C2A—C3A—C4A | 178.8 (2) |
C12—C3—C4—C13 | 179.4 (2) | C2A—C3A—C4A—C13A | −1.2 (3) |
C2—C3—C4—C13 | 0.7 (3) | C12A—C3A—C4A—C13A | 178.3 (2) |
C13—C5—N6—C15 | −125.7 (2) | C13A—C5A—N6A—C15A | 120.9 (2) |
C18—C5—N6—C15 | 104.1 (2) | C18A—C5A—N6A—C15A | −110.4 (2) |
C13—C5—N6—C7 | 41.7 (3) | C13A—C5A—N6A—C7A | −46.4 (3) |
C18—C5—N6—C7 | −88.5 (2) | C18A—C5A—N6A—C7A | 82.2 (2) |
C15—N6—C7—C24 | −70.2 (3) | C15A—N6A—C7A—C24A | 73.3 (3) |
C5—N6—C7—C24 | 123.1 (2) | C5A—N6A—C7A—C24A | −119.6 (2) |
C15—N6—C7—C8 | 166.9 (2) | C15A—N6A—C7A—C8A | −161.7 (2) |
C5—N6—C7—C8 | 0.1 (3) | C5A—N6A—C7A—C8A | 5.4 (3) |
N6—C7—C8—C14 | −44.3 (3) | N6A—C7A—C8A—C14A | 41.8 (3) |
C24—C7—C8—C14 | −170.8 (2) | C24A—C7A—C8A—C14A | 168.8 (2) |
N1—C2—C9—C10 | 178.6 (2) | N1A—C2A—C9A—C10A | 179.7 (2) |
C3—C2—C9—C10 | −0.9 (4) | C3A—C2A—C9A—C10A | 0.6 (4) |
C2—C9—C10—C11 | 0.3 (4) | C2A—C9A—C10A—C11A | −0.3 (4) |
C9—C10—C11—C12 | 0.1 (4) | C9A—C10A—C11A—C12A | 0.1 (5) |
C10—C11—C12—C3 | 0.3 (4) | C10A—C11A—C12A—C3A | −0.2 (4) |
C4—C3—C12—C11 | −179.6 (2) | C2A—C3A—C12A—C11A | 0.6 (4) |
C2—C3—C12—C11 | −0.9 (4) | C4A—C3A—C12A—C11A | −178.9 (2) |
C3—C4—C13—C14 | −1.3 (3) | C3A—C4A—C13A—C14A | 0.6 (3) |
C3—C4—C13—C5 | 179.8 (2) | C3A—C4A—C13A—C5A | 179.0 (2) |
N6—C5—C13—C4 | 137.6 (2) | N6A—C5A—C13A—C4A | −137.0 (2) |
C18—C5—C13—C4 | −93.3 (3) | C18A—C5A—C13A—C4A | 95.7 (3) |
N6—C5—C13—C14 | −41.4 (3) | N6A—C5A—C13A—C14A | 41.4 (3) |
C18—C5—C13—C14 | 87.8 (3) | C18A—C5A—C13A—C14A | −85.9 (3) |
C2—N1—C14—C13 | 0.5 (3) | C2A—N1A—C14A—C13A | −2.8 (3) |
C2—N1—C14—C8 | −178.5 (2) | C2A—N1A—C14A—C8A | 175.8 (2) |
C4—C13—C14—N1 | 0.7 (3) | C4A—C13A—C14A—N1A | 1.4 (3) |
C5—C13—C14—N1 | 179.7 (2) | C5A—C13A—C14A—N1A | −177.0 (2) |
C4—C13—C14—C8 | 179.6 (2) | C4A—C13A—C14A—C8A | −177.2 (2) |
C5—C13—C14—C8 | −1.3 (3) | C5A—C13A—C14A—C8A | 4.3 (3) |
C7—C8—C14—N1 | −135.0 (2) | C7A—C8A—C14A—N1A | 133.3 (2) |
C7—C8—C14—C13 | 46.0 (3) | C7A—C8A—C14A—C13A | −48.0 (3) |
C7—N6—C15—O17 | −176.4 (2) | C7A—N6A—C15A—O17A | 173.7 (2) |
C5—N6—C15—O17 | −9.1 (3) | C5A—N6A—C15A—O17A | 6.5 (4) |
C7—N6—C15—C16 | 3.2 (3) | C7A—N6A—C15A—C16A | −6.3 (4) |
C5—N6—C15—C16 | 170.5 (2) | C5A—N6A—C15A—C16A | −173.5 (2) |
N6—C5—C18—C23 | 116.8 (3) | N6A—C5A—C18A—C19A | −116.2 (3) |
C13—C5—C18—C23 | −10.5 (3) | C13A—C5A—C18A—C19A | 9.5 (4) |
N6—C5—C18—C19 | −65.2 (3) | N6A—C5A—C18A—C23A | 65.3 (3) |
C13—C5—C18—C19 | 167.5 (2) | C13A—C5A—C18A—C23A | −169.0 (2) |
C23—C18—C19—C20 | 0.2 (4) | C23A—C18A—C19A—C20A | −1.4 (4) |
C5—C18—C19—C20 | −177.9 (3) | C5A—C18A—C19A—C20A | −179.9 (3) |
C18—C19—C20—C21 | −0.5 (5) | C18A—C19A—C20A—C21A | 0.3 (5) |
C19—C20—C21—C22 | 0.4 (6) | C19A—C20A—C21A—C22A | 0.8 (5) |
C20—C21—C22—C23 | 0.1 (5) | C20A—C21A—C22A—C23A | −0.7 (5) |
C19—C18—C23—C22 | 0.3 (4) | C21A—C22A—C23A—C18A | −0.4 (5) |
C5—C18—C23—C22 | 178.3 (3) | C19A—C18A—C23A—C22A | 1.4 (4) |
C21—C22—C23—C18 | −0.4 (5) | C5A—C18A—C23A—C22A | 180.0 (3) |
N6—C7—C24—C25 | 138.5 (2) | N6A—C7A—C24A—C25A | 38.6 (3) |
C8—C7—C24—C25 | −97.2 (3) | C8A—C7A—C24A—C25A | −86.8 (3) |
N6—C7—C24—C29 | −46.1 (3) | N6A—C7A—C24A—C29A | −143.9 (2) |
C8—C7—C24—C29 | 78.1 (3) | C8A—C7A—C24A—C29A | 90.6 (3) |
C29—C24—C25—C26 | −0.9 (4) | C29A—C24A—C25A—C26A | 0.3 (4) |
C7—C24—C25—C26 | 174.6 (2) | C7A—C24A—C25A—C26A | 177.7 (2) |
C24—C25—C26—C27 | 0.6 (5) | C24A—C25A—C26A—C27A | 0.5 (4) |
C25—C26—C27—C28 | 0.2 (5) | C25A—C26A—C27A—C28A | −1.0 (5) |
C26—C27—C28—C29 | −0.8 (4) | C26A—C27A—C28A—C29A | 0.6 (4) |
C27—C28—C29—C24 | 0.5 (4) | C25A—C24A—C29A—C28A | −0.7 (4) |
C25—C24—C29—C28 | 0.3 (4) | C7A—C24A—C29A—C28A | −178.2 (2) |
C7—C24—C29—C28 | −175.1 (2) | C27A—C28A—C29A—C24A | 0.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O17 | 0.98 (2) | 2.21 (2) | 2.685 (3) | 109 |
C5A—H5A···O17A | 0.95 (2) | 2.27 (2) | 2.732 (3) | 110 |
C7A—H7A···O17 | 1.01 (2) | 2.45 (2) | 3.322 (3) | 145 |
C9A—H9A···O17Ai | 1.04 (2) | 2.37 (2) | 3.325 (3) | 153 |
C11A—H11A···O17ii | 0.93 (2) | 2.47 (2) | 3.276 (5) | 145 |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z. |
Experimental details
Crystal data |
Chemical formula | C26H22N2O |
Mr | 378.46 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.394 (2), 10.493 (3), 20.265 (4) |
α, β, γ (°) | 76.03 (2), 79.83 (2), 72.21 (2) |
V (Å3) | 2029.6 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.05 × 0.05 × 0.04 |
|
Data collection |
Diffractometer | Siemens P3 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9786, 9279, 4446 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.654 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.167, 0.99 |
No. of reflections | 9279 |
No. of parameters | 566 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.38 |
Selected geometric parameters (Å, º) topN1—C14 | 1.309 (3) | N1A—C14A | 1.319 (3) |
N1—C2 | 1.368 (3) | N1A—C2A | 1.368 (3) |
C4—C13 | 1.351 (3) | C4A—C13A | 1.359 (3) |
C5—N6 | 1.483 (3) | C5A—N6A | 1.487 (3) |
C5—C13 | 1.499 (3) | C5A—C13A | 1.509 (3) |
C5—C18 | 1.525 (3) | C5A—C18A | 1.519 (3) |
N6—C15 | 1.365 (3) | N6A—C15A | 1.362 (3) |
N6—C7 | 1.481 (3) | N6A—C7A | 1.479 (3) |
C7—C24 | 1.508 (3) | C7A—C24A | 1.516 (3) |
C7—C8 | 1.540 (3) | C7A—C8A | 1.537 (3) |
C8—C14 | 1.491 (3) | C8A—C14A | 1.490 (3) |
C13—C14 | 1.421 (3) | C13A—C14A | 1.410 (3) |
C15—O17 | 1.229 (3) | C15A—O17A | 1.225 (3) |
C15—C16 | 1.507 (4) | C15A—C16A | 1.500 (4) |
| | | |
C14—N1—C2 | 116.5 (2) | C14A—N1A—C2A | 118.2 (2) |
N1—C2—C9 | 117.8 (2) | N1A—C2A—C3A | 122.3 (2) |
N1—C2—C3 | 123.4 (2) | N1A—C2A—C9A | 118.5 (2) |
C13—C4—C3 | 119.5 (2) | C13A—C4A—C3A | 120.1 (2) |
N6—C5—C13 | 109.67 (19) | N6A—C5A—C13A | 109.29 (19) |
N6—C5—C18 | 113.21 (19) | N6A—C5A—C18A | 112.41 (19) |
C13—C5—C18 | 115.2 (2) | C13A—C5A—C18A | 114.8 (2) |
C15—N6—C7 | 121.4 (2) | C15A—N6A—C7A | 120.9 (2) |
C15—N6—C5 | 116.6 (2) | C15A—N6A—C5A | 118.2 (2) |
C7—N6—C5 | 120.71 (18) | C7A—N6A—C5A | 119.67 (18) |
N6—C7—C24 | 114.60 (19) | N6A—C7A—C24A | 113.91 (19) |
N6—C7—C8 | 110.8 (2) | N6A—C7A—C8A | 111.00 (19) |
C24—C7—C8 | 108.30 (19) | C24A—C7A—C8A | 110.13 (19) |
C14—C8—C7 | 112.5 (2) | C14A—C8A—C7A | 112.5 (2) |
C10—C9—C2 | 119.9 (3) | C10A—C9A—C2A | 119.9 (3) |
C9—C10—C11 | 121.0 (3) | C9A—C10A—C11A | 121.1 (3) |
C12—C11—C10 | 121.0 (3) | C12A—C11A—C10A | 120.3 (3) |
C11—C12—C3 | 119.4 (3) | C11A—C12A—C3A | 120.6 (3) |
C4—C13—C14 | 118.8 (2) | C4A—C13A—C14A | 118.4 (2) |
C4—C13—C5 | 122.8 (2) | C4A—C13A—C5A | 124.1 (2) |
C14—C13—C5 | 118.4 (2) | C14A—C13A—C5A | 117.4 (2) |
N1—C14—C13 | 124.6 (2) | N1A—C14A—C13A | 123.6 (2) |
N1—C14—C8 | 119.3 (2) | N1A—C14A—C8A | 119.9 (2) |
C13—C14—C8 | 116.2 (2) | C13A—C14A—C8A | 116.5 (2) |
O17—C15—N6 | 121.1 (2) | O17A—C15A—N6A | 122.1 (3) |
O17—C15—C16 | 120.1 (2) | O17A—C15A—C16A | 119.3 (2) |
N6—C15—C16 | 118.8 (2) | N6A—C15A—C16A | 118.7 (2) |
C23—C18—C19 | 117.4 (3) | C19A—C18A—C5A | 123.5 (2) |
C23—C18—C5 | 124.1 (2) | C23A—C18A—C5A | 118.2 (2) |
| | | |
C13—C5—N6—C7 | 41.7 (3) | C13A—C5A—N6A—C7A | −46.4 (3) |
C5—N6—C7—C8 | 0.1 (3) | C5A—N6A—C7A—C8A | 5.4 (3) |
N6—C7—C8—C14 | −44.3 (3) | N6A—C7A—C8A—C14A | 41.8 (3) |
C24—C7—C8—C14 | −170.8 (2) | C24A—C7A—C8A—C14A | 168.8 (2) |
N6—C5—C13—C14 | −41.4 (3) | N6A—C5A—C13A—C14A | 41.4 (3) |
C5—C13—C14—C8 | −1.3 (3) | C5A—C13A—C14A—C8A | 4.3 (3) |
C7—C8—C14—C13 | 46.0 (3) | C7A—C8A—C14A—C13A | −48.0 (3) |
C7—N6—C15—O17 | −176.4 (2) | C7A—N6A—C15A—O17A | 173.7 (2) |
C5—N6—C15—O17 | −9.1 (3) | C5A—N6A—C15A—O17A | 6.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O17 | 0.98 (2) | 2.21 (2) | 2.685 (3) | 109 |
C5A—H5A···O17A | 0.95 (2) | 2.27 (2) | 2.732 (3) | 110 |
C7A—H7A···O17 | 1.01 (2) | 2.45 (2) | 3.322 (3) | 145 |
C9A—H9A···O17Ai | 1.04 (2) | 2.37 (2) | 3.325 (3) | 153 |
C11A—H11A···O17ii | 0.93 (2) | 2.47 (2) | 3.276 (5) | 145 |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z. |
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Naphthyridine derivatives have extensive pharmacological properties (Di Braccio et al., 1997; Hong et al., 1997; Chen et al., 1997; Mohan & Mishra, 1997; Damon & Nadelson, 1981; Singh et al., 1995). Structural data for only a few 1,6-naphthyridines are available in the literature (Balogh et al., 1986; Anderez et al., 1992; Govindasamy et al., 2000). The present investigation of N(2)-acetyl-1,3-diphenyl-1,2,3,4-tetrahydrobenzo[b]-1,6-naphthyridine, (I), was undertaken to establish the molecular structure and to determine the precise conformational changes caused by the substituents on the 1,6-naphthyridine ring system in the molecule of the crystalline acetylated product.
As shown by the X-ray analysis, the tetrahydro-1,6-naphthyridine ring has a boat conformation. The average numerical torsion angles, 43.4 (3) and 44.4 (3)°, involving the four C atoms of the plane of the boat show deviation from the ideal value of 54° (Nasipuri, 1994) due to the presence of planar coordinated N atoms. The C14—C8—C7—C24 and C14A—C8A—C7A—C24A torsion angles of -170.8 (2) and 168.8 (2)° show that the phenyl groups attached to C7 and C7A are equatorially disposed in the above ring system. The torsion angles 87.8 (3) and -85.9 (3)°, defined by the atoms C14—C13—C5—C18 and C14A—C13A—C5A—C18A, respectively, show that the phenyl groups attached to C5 and C5A are axially oriented in the naphthyridine ring. The sum of the bond angles around N6 and N6A, 358.7 (2) and 358.8 (2)°, show the near coplanar orientation of the acetyl group with the C5—N6—C7 part of the molecule. The atoms C5, C5A, C7 and C7A are chiral, their relative configurations being either SR or RS as revealed by the use of PLATON97 (Spek, 1990). The intermolecular and intramolecular C—H···O hydrogen bonds involving the acetyl O and the C atoms of the naphthyridine ring are listed in Table 2.