In the title compoumd, C
23H
21N
3O
2, all the bond lengths and angles have normal values. The naphthalene ring system and the pyrazole ring are approximately coplanar and are linked by an HC=N unit, forming a conjugated system. In the crystal structure, weak C—H
O interactions link the molecules, forming a layer structure.
Supporting information
CCDC reference: 636193
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C)= 0.002 Å
- R factor = 0.036
- wR factor = 0.076
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Version 1.4.1; Macrae et al., 2006); software used to prepare material for publication: SHELXTL.
(
E)-4-(6-Methoxy-2-naphthylmethylideneamino)-1,5-dimethyl-2-phenyl-
1
H-pyrazol-3(2
H)-one
top
Crystal data top
C23H21N3O2 | F(000) = 784 |
Mr = 371.43 | Dx = 1.272 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4071 reflections |
a = 8.102 (2) Å | θ = 2.4–25.2° |
b = 7.1317 (19) Å | µ = 0.08 mm−1 |
c = 33.558 (9) Å | T = 273 K |
β = 90.761 (4)° | Block, yellow |
V = 1938.9 (9) Å3 | 0.30 × 0.26 × 0.24 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD diffractometer | 1910 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 26.0°, θmin = 2.4° |
φ and ω scans | h = −9→9 |
11973 measured reflections | k = −8→8 |
3742 independent reflections | l = −41→41 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3 |
3742 reflections | (Δ/σ)max < 0.001 |
256 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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 | |
C1 | 0.99423 (17) | 0.6537 (2) | 0.22771 (4) | 0.0456 (4) | |
C2 | 1.07250 (18) | 0.7784 (2) | 0.25567 (4) | 0.0484 (4) | |
C3 | 0.95695 (17) | 0.4913 (2) | 0.24684 (5) | 0.0471 (4) | |
C4 | 0.88471 (19) | 0.3170 (2) | 0.23002 (5) | 0.0675 (5) | |
H4A | 0.9659 | 0.2190 | 0.2308 | 0.101* | |
H4B | 0.8503 | 0.3388 | 0.2029 | 0.101* | |
H4C | 0.7911 | 0.2804 | 0.2454 | 0.101* | |
C5 | 1.0526 (2) | 0.3455 (2) | 0.31043 (4) | 0.0637 (5) | |
H5A | 0.9800 | 0.2409 | 0.3060 | 0.096* | |
H5B | 1.0515 | 0.3797 | 0.3381 | 0.096* | |
H5C | 1.1627 | 0.3116 | 0.3031 | 0.096* | |
C6 | 1.08658 (19) | 0.7626 (2) | 0.32955 (4) | 0.0469 (4) | |
C7 | 0.96432 (19) | 0.7318 (2) | 0.35721 (5) | 0.0555 (4) | |
H7 | 0.8765 | 0.6522 | 0.3513 | 0.067* | |
C8 | 0.9743 (2) | 0.8204 (3) | 0.39359 (5) | 0.0660 (5) | |
H8 | 0.8935 | 0.7986 | 0.4125 | 0.079* | |
C9 | 1.1020 (2) | 0.9404 (2) | 0.40238 (5) | 0.0679 (5) | |
H9 | 1.1076 | 0.9999 | 0.4270 | 0.081* | |
C10 | 1.2216 (2) | 0.9720 (2) | 0.37445 (5) | 0.0618 (5) | |
H10 | 1.3074 | 1.0547 | 0.3802 | 0.074* | |
C11 | 1.2155 (2) | 0.8828 (2) | 0.33820 (5) | 0.0543 (4) | |
H11 | 1.2978 | 0.9032 | 0.3196 | 0.065* | |
C12 | 0.97477 (18) | 0.8426 (2) | 0.17111 (5) | 0.0522 (4) | |
H12 | 1.0294 | 0.9371 | 0.1851 | 0.063* | |
C13 | 0.92120 (18) | 0.8757 (2) | 0.13012 (4) | 0.0486 (4) | |
C14 | 0.95159 (18) | 1.0442 (2) | 0.11198 (5) | 0.0515 (4) | |
H14 | 1.0087 | 1.1364 | 0.1261 | 0.062* | |
C15 | 0.89886 (18) | 1.0819 (2) | 0.07259 (5) | 0.0474 (4) | |
C16 | 0.92470 (19) | 1.2560 (2) | 0.05364 (5) | 0.0587 (5) | |
H16 | 0.9810 | 1.3507 | 0.0672 | 0.070* | |
C17 | 0.8688 (2) | 1.2871 (3) | 0.01607 (5) | 0.0628 (5) | |
H17 | 0.8854 | 1.4036 | 0.0043 | 0.075* | |
C18 | 0.78663 (19) | 1.1467 (3) | −0.00534 (5) | 0.0567 (5) | |
C19 | 0.75969 (19) | 0.9768 (3) | 0.01155 (5) | 0.0557 (4) | |
H19 | 0.7049 | 0.8838 | −0.0028 | 0.067* | |
C20 | 0.81493 (18) | 0.9409 (2) | 0.05106 (5) | 0.0485 (4) | |
C21 | 0.78510 (19) | 0.7677 (2) | 0.07011 (5) | 0.0602 (5) | |
H21 | 0.7292 | 0.6735 | 0.0563 | 0.072* | |
C22 | 0.83652 (19) | 0.7362 (2) | 0.10820 (5) | 0.0574 (4) | |
H22 | 0.8156 | 0.6208 | 0.1200 | 0.069* | |
C23 | 0.6579 (2) | 1.0601 (3) | −0.06691 (5) | 0.0763 (6) | |
H23A | 0.7293 | 0.9539 | −0.0702 | 0.114* | |
H23B | 0.6309 | 1.1125 | −0.0925 | 0.114* | |
H23C | 0.5585 | 1.0209 | −0.0541 | 0.114* | |
N1 | 1.08013 (14) | 0.67643 (18) | 0.29146 (4) | 0.0500 (3) | |
N2 | 0.99672 (15) | 0.50504 (18) | 0.28617 (4) | 0.0504 (3) | |
N3 | 0.94767 (15) | 0.68509 (19) | 0.18819 (4) | 0.0511 (4) | |
O1 | 1.12068 (13) | 0.94131 (16) | 0.25253 (3) | 0.0644 (3) | |
O2 | 0.73941 (14) | 1.19784 (17) | −0.04305 (3) | 0.0756 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0455 (10) | 0.0437 (11) | 0.0478 (10) | 0.0030 (8) | 0.0030 (8) | 0.0019 (9) |
C2 | 0.0533 (10) | 0.0411 (11) | 0.0510 (10) | 0.0021 (9) | 0.0036 (8) | 0.0026 (9) |
C3 | 0.0463 (10) | 0.0441 (12) | 0.0510 (11) | 0.0026 (8) | 0.0026 (8) | −0.0035 (9) |
C4 | 0.0760 (13) | 0.0553 (13) | 0.0712 (11) | −0.0124 (10) | 0.0000 (10) | −0.0036 (10) |
C5 | 0.0828 (12) | 0.0468 (12) | 0.0615 (11) | 0.0012 (10) | 0.0010 (9) | 0.0107 (9) |
C6 | 0.0530 (10) | 0.0405 (11) | 0.0473 (10) | 0.0026 (8) | −0.0008 (8) | 0.0019 (8) |
C7 | 0.0535 (11) | 0.0552 (12) | 0.0579 (11) | −0.0054 (9) | 0.0046 (9) | −0.0040 (9) |
C8 | 0.0702 (13) | 0.0658 (14) | 0.0623 (12) | −0.0041 (11) | 0.0135 (9) | −0.0070 (10) |
C9 | 0.0892 (14) | 0.0583 (14) | 0.0561 (11) | −0.0014 (11) | −0.0004 (11) | −0.0080 (9) |
C10 | 0.0674 (12) | 0.0506 (13) | 0.0670 (12) | −0.0102 (9) | −0.0116 (10) | 0.0003 (10) |
C11 | 0.0540 (11) | 0.0502 (12) | 0.0587 (11) | −0.0033 (9) | 0.0020 (8) | 0.0037 (9) |
C12 | 0.0548 (11) | 0.0501 (12) | 0.0516 (11) | 0.0037 (9) | 0.0001 (8) | −0.0032 (9) |
C13 | 0.0500 (10) | 0.0464 (12) | 0.0494 (10) | 0.0044 (9) | 0.0004 (8) | 0.0009 (9) |
C14 | 0.0515 (10) | 0.0484 (12) | 0.0547 (11) | −0.0028 (9) | 0.0004 (8) | −0.0048 (9) |
C15 | 0.0477 (10) | 0.0433 (11) | 0.0514 (10) | 0.0005 (8) | 0.0024 (8) | 0.0009 (9) |
C16 | 0.0657 (11) | 0.0491 (13) | 0.0612 (12) | −0.0095 (9) | −0.0002 (9) | 0.0001 (10) |
C17 | 0.0773 (13) | 0.0488 (13) | 0.0622 (12) | −0.0066 (10) | 0.0002 (10) | 0.0100 (10) |
C18 | 0.0585 (11) | 0.0577 (13) | 0.0538 (11) | 0.0021 (10) | −0.0007 (9) | 0.0060 (10) |
C19 | 0.0611 (11) | 0.0509 (13) | 0.0550 (11) | −0.0003 (9) | −0.0062 (9) | −0.0012 (9) |
C20 | 0.0502 (10) | 0.0435 (12) | 0.0518 (10) | 0.0025 (9) | 0.0000 (8) | 0.0004 (9) |
C21 | 0.0742 (12) | 0.0450 (12) | 0.0612 (11) | −0.0080 (9) | −0.0124 (9) | −0.0001 (10) |
C22 | 0.0704 (11) | 0.0433 (11) | 0.0583 (11) | −0.0027 (9) | −0.0059 (9) | 0.0067 (9) |
C23 | 0.0807 (13) | 0.0883 (16) | 0.0595 (12) | −0.0023 (11) | −0.0138 (10) | 0.0002 (11) |
N1 | 0.0618 (9) | 0.0400 (9) | 0.0481 (8) | −0.0065 (7) | 0.0025 (6) | 0.0006 (7) |
N2 | 0.0617 (9) | 0.0374 (9) | 0.0522 (9) | −0.0026 (7) | 0.0013 (7) | 0.0043 (7) |
N3 | 0.0525 (8) | 0.0499 (10) | 0.0510 (9) | 0.0050 (7) | 0.0012 (6) | 0.0010 (7) |
O1 | 0.0890 (9) | 0.0444 (8) | 0.0597 (7) | −0.0152 (7) | −0.0038 (6) | 0.0060 (6) |
O2 | 0.0964 (9) | 0.0711 (10) | 0.0587 (8) | −0.0038 (7) | −0.0166 (7) | 0.0149 (7) |
Geometric parameters (Å, º) top
C1—C3 | 1.361 (2) | C12—N3 | 1.2811 (18) |
C1—N3 | 1.3923 (18) | C12—C13 | 1.456 (2) |
C1—C2 | 1.434 (2) | C12—H12 | 0.930 |
C2—O1 | 1.2307 (17) | C13—C14 | 1.371 (2) |
C2—N1 | 1.4045 (18) | C13—C22 | 1.410 (2) |
C3—N2 | 1.3579 (18) | C14—C15 | 1.410 (2) |
C3—C4 | 1.482 (2) | C14—H14 | 0.930 |
C4—H4A | 0.960 | C15—C20 | 1.408 (2) |
C4—H4B | 0.960 | C15—C16 | 1.412 (2) |
C4—H4C | 0.960 | C16—C17 | 1.352 (2) |
C5—N2 | 1.4669 (18) | C16—H16 | 0.930 |
C5—H5A | 0.960 | C17—C18 | 1.396 (2) |
C5—H5B | 0.960 | C17—H17 | 0.930 |
C5—H5C | 0.960 | C18—C19 | 1.357 (2) |
C6—C11 | 1.379 (2) | C18—O2 | 1.3666 (18) |
C6—C7 | 1.3839 (18) | C19—C20 | 1.417 (2) |
C6—N1 | 1.4186 (18) | C19—H19 | 0.930 |
C7—C8 | 1.376 (2) | C20—C21 | 1.413 (2) |
C7—H7 | 0.930 | C21—C22 | 1.358 (2) |
C8—C9 | 1.371 (2) | C21—H21 | 0.930 |
C8—H8 | 0.930 | C22—H22 | 0.930 |
C9—C10 | 1.376 (2) | C23—O2 | 1.4245 (19) |
C9—H9 | 0.930 | C23—H23A | 0.960 |
C10—C11 | 1.373 (2) | C23—H23B | 0.960 |
C10—H10 | 0.930 | C23—H23C | 0.960 |
C11—H11 | 0.930 | N1—N2 | 1.4068 (16) |
| | | |
C3—C1—N3 | 121.81 (15) | C14—C13—C12 | 120.58 (15) |
C3—C1—C2 | 108.56 (14) | C22—C13—C12 | 121.00 (15) |
N3—C1—C2 | 129.47 (15) | C13—C14—C15 | 121.98 (15) |
O1—C2—N1 | 123.48 (15) | C13—C14—H14 | 119.0 |
O1—C2—C1 | 131.84 (15) | C15—C14—H14 | 119.0 |
N1—C2—C1 | 104.63 (14) | C20—C15—C14 | 118.89 (15) |
N2—C3—C1 | 110.22 (14) | C20—C15—C16 | 118.07 (14) |
N2—C3—C4 | 121.21 (14) | C14—C15—C16 | 123.03 (15) |
C1—C3—C4 | 128.57 (15) | C17—C16—C15 | 120.95 (16) |
C3—C4—H4A | 109.5 | C17—C16—H16 | 119.5 |
C3—C4—H4B | 109.5 | C15—C16—H16 | 119.5 |
H4A—C4—H4B | 109.5 | C16—C17—C18 | 120.91 (16) |
C3—C4—H4C | 109.5 | C16—C17—H17 | 119.5 |
H4A—C4—H4C | 109.5 | C18—C17—H17 | 119.5 |
H4B—C4—H4C | 109.5 | C19—C18—O2 | 125.49 (16) |
N2—C5—H5A | 109.5 | C19—C18—C17 | 120.24 (16) |
N2—C5—H5B | 109.5 | O2—C18—C17 | 114.27 (16) |
H5A—C5—H5B | 109.5 | C18—C19—C20 | 120.13 (16) |
N2—C5—H5C | 109.5 | C18—C19—H19 | 119.9 |
H5A—C5—H5C | 109.5 | C20—C19—H19 | 119.9 |
H5B—C5—H5C | 109.5 | C15—C20—C21 | 118.46 (15) |
C11—C6—C7 | 120.29 (15) | C15—C20—C19 | 119.67 (15) |
C11—C6—N1 | 118.53 (14) | C21—C20—C19 | 121.85 (16) |
C7—C6—N1 | 121.16 (15) | C22—C21—C20 | 121.23 (16) |
C8—C7—C6 | 119.21 (16) | C22—C21—H21 | 119.4 |
C8—C7—H7 | 120.4 | C20—C21—H21 | 119.4 |
C6—C7—H7 | 120.4 | C21—C22—C13 | 121.01 (15) |
C9—C8—C7 | 120.83 (16) | C21—C22—H22 | 119.5 |
C9—C8—H8 | 119.6 | C13—C22—H22 | 119.5 |
C7—C8—H8 | 119.6 | O2—C23—H23A | 109.5 |
C8—C9—C10 | 119.47 (16) | O2—C23—H23B | 109.5 |
C8—C9—H9 | 120.3 | H23A—C23—H23B | 109.5 |
C10—C9—H9 | 120.3 | O2—C23—H23C | 109.5 |
C11—C10—C9 | 120.68 (16) | H23A—C23—H23C | 109.5 |
C11—C10—H10 | 119.7 | H23B—C23—H23C | 109.5 |
C9—C10—H10 | 119.7 | C2—N1—N2 | 109.05 (12) |
C10—C11—C6 | 119.50 (15) | C2—N1—C6 | 123.14 (14) |
C10—C11—H11 | 120.2 | N2—N1—C6 | 120.13 (12) |
C6—C11—H11 | 120.2 | C3—N2—N1 | 107.03 (12) |
N3—C12—C13 | 120.94 (15) | C3—N2—C5 | 123.42 (13) |
N3—C12—H12 | 119.5 | N1—N2—C5 | 117.36 (12) |
C13—C12—H12 | 119.5 | C12—N3—C1 | 121.40 (14) |
C14—C13—C22 | 118.42 (14) | C18—O2—C23 | 117.30 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1i | 0.96 | 2.45 | 3.371 (2) | 161 |
C9—H9···O2ii | 0.93 | 2.60 | 3.346 (2) | 137 |
Symmetry codes: (i) x, y−1, z; (ii) x+1/2, −y+5/2, z+1/2. |