In the title compound, C
25H
21NO
2, the coumarin moiety is planar and the attached dimethylamino group is twisted around the N—C bond. The dihedral angle between the two phenyl rings is 75.45 (9)°. The crystal structure is stabilized by weak intermolecular C—H
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O interactions and van der Waals forces.
Supporting information
CCDC reference: 189901
Key indicators
- Single-crystal X-ray study
- T = 213 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.054
- wR factor = 0.141
- Data-to-parameter ratio = 15.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
4-(
N,
N-Dimethylamino)-3-(2,2-diphenylethenyl)coumarin
top
Crystal data top
C25H21NO2 | F(000) = 776 |
Mr = 367.43 | Dx = 1.264 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.4191 (3) Å | Cell parameters from 7060 reflections |
b = 8.8571 (2) Å | θ = 2.6–28.3° |
c = 17.6617 (3) Å | µ = 0.08 mm−1 |
β = 96.313 (1)° | T = 213 K |
V = 1930.96 (7) Å3 | Block, yellow |
Z = 4 | 0.44 × 0.38 × 0.26 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2883 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.076 |
Graphite monochromator | θmax = 28.3°, θmin = 2.6° |
Detector resolution: 8.33 pixels mm-1 | h = −16→12 |
ω scans | k = −11→11 |
11044 measured reflections | l = −22→23 |
4609 independent reflections | |
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)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.141 | w = 1/[σ2(Fo2) + (0.0397P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max < 0.001 |
4609 reflections | Δρmax = 0.32 e Å−3 |
308 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.022 (2) |
Special details top
Experimental. The data collection covered over a hemisphere of reciprocal space by a
combination of three sets of exposures; each set had a different φ angle (0,
88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω.
The crystal-to-detector distance was 5 cm and the detector swing angle was
-35°. Crystal decay was monitored by repeating fifty initial frames at the
end of data collection and analysing the intensity of duplicate reflections,
and was found to be negligible. |
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 | |
O1 | 0.44933 (9) | 0.25545 (13) | 0.06460 (6) | 0.0297 (3) | |
O2 | 0.47269 (11) | 0.30924 (16) | 0.18691 (7) | 0.0470 (4) | |
N1 | 0.24974 (13) | −0.11378 (17) | 0.10474 (9) | 0.0395 (4) | |
C1 | 0.42952 (13) | 0.22487 (19) | 0.13849 (10) | 0.0287 (4) | |
C2 | 0.40755 (12) | 0.16396 (18) | 0.00553 (9) | 0.0264 (4) | |
C3 | 0.44099 (14) | 0.1977 (2) | −0.06524 (10) | 0.0322 (4) | |
C4 | 0.40753 (14) | 0.1062 (2) | −0.12699 (10) | 0.0353 (4) | |
C5 | 0.34298 (15) | −0.0189 (2) | −0.11686 (11) | 0.0363 (4) | |
C6 | 0.31041 (15) | −0.0506 (2) | −0.04678 (10) | 0.0328 (4) | |
C7 | 0.33927 (13) | 0.04337 (18) | 0.01699 (9) | 0.0259 (4) | |
C8 | 0.31237 (12) | 0.01255 (18) | 0.09400 (10) | 0.0267 (4) | |
C9 | 0.35765 (12) | 0.10239 (18) | 0.15262 (9) | 0.0248 (4) | |
C10 | 0.34055 (13) | 0.08644 (19) | 0.23408 (10) | 0.0267 (4) | |
C11 | 0.24704 (13) | 0.10601 (17) | 0.26399 (9) | 0.0239 (3) | |
C12 | 0.14694 (13) | 0.16053 (19) | 0.21783 (9) | 0.0266 (4) | |
C13 | 0.14608 (15) | 0.2995 (2) | 0.18030 (11) | 0.0369 (4) | |
H13 | 0.2092 | 0.3566 | 0.1826 | 0.044* | |
C14 | 0.05216 (18) | 0.3532 (3) | 0.13972 (11) | 0.0471 (6) | |
C15 | −0.04232 (18) | 0.2695 (3) | 0.13516 (12) | 0.0511 (6) | |
C16 | −0.04269 (15) | 0.1327 (3) | 0.17187 (13) | 0.0502 (6) | |
H16 | −0.1061 | 0.0760 | 0.1686 | 0.060* | |
C17 | 0.05088 (14) | 0.0779 (2) | 0.21394 (11) | 0.0370 (4) | |
C18 | 0.23987 (12) | 0.07985 (17) | 0.34628 (9) | 0.0237 (3) | |
C19 | 0.16655 (14) | 0.16193 (19) | 0.38513 (10) | 0.0280 (4) | |
C20 | 0.16296 (15) | 0.1440 (2) | 0.46256 (10) | 0.0335 (4) | |
C21 | 0.23241 (16) | 0.0427 (2) | 0.50356 (11) | 0.0359 (4) | |
C22 | 0.30486 (15) | −0.0403 (2) | 0.46586 (10) | 0.0335 (4) | |
C23 | 0.30819 (13) | −0.02326 (19) | 0.38823 (10) | 0.0279 (4) | |
C24 | 0.2694 (2) | −0.2094 (2) | 0.17168 (12) | 0.0529 (6) | |
H24A | 0.3436 | −0.1996 | 0.1929 | 0.079* | |
H24B | 0.2547 | −0.3126 | 0.1575 | 0.079* | |
H24C | 0.2228 | −0.1790 | 0.2088 | 0.079* | |
C25 | 0.14270 (16) | −0.1311 (3) | 0.06209 (13) | 0.0521 (6) | |
H25A | 0.1309 | −0.0513 | 0.0253 | 0.078* | |
H25B | 0.0882 | −0.1266 | 0.0966 | 0.078* | |
H25C | 0.1387 | −0.2267 | 0.0364 | 0.078* | |
H23 | 0.3582 (14) | −0.080 (2) | 0.3615 (10) | 0.031 (5)* | |
H10 | 0.4057 (13) | 0.0629 (19) | 0.2706 (10) | 0.033 (5)* | |
H4 | 0.4324 (14) | 0.128 (2) | −0.1786 (12) | 0.038 (5)* | |
H3 | 0.4840 (15) | 0.287 (2) | −0.0689 (11) | 0.036 (5)* | |
H19 | 0.1172 (14) | 0.239 (2) | 0.3602 (10) | 0.036 (5)* | |
H17 | 0.0480 (14) | −0.022 (2) | 0.2415 (11) | 0.043 (6)* | |
H20 | 0.1100 (15) | 0.203 (2) | 0.4941 (11) | 0.042 (5)* | |
H15 | −0.1079 (16) | 0.309 (2) | 0.1073 (12) | 0.046 (5)* | |
H22 | 0.3516 (17) | −0.115 (2) | 0.5005 (13) | 0.061 (6)* | |
H6 | 0.2655 (16) | −0.135 (2) | −0.0459 (12) | 0.053 (6)* | |
H14 | 0.0519 (17) | 0.451 (3) | 0.1174 (14) | 0.064 (7)* | |
H21 | 0.2299 (16) | 0.031 (2) | 0.5524 (13) | 0.052 (6)* | |
H5 | 0.3199 (15) | −0.086 (2) | −0.1649 (12) | 0.050 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0318 (7) | 0.0344 (7) | 0.0233 (6) | −0.0042 (5) | 0.0051 (5) | −0.0003 (5) |
O2 | 0.0544 (9) | 0.0575 (9) | 0.0307 (8) | −0.0254 (7) | 0.0112 (6) | −0.0136 (6) |
N1 | 0.0473 (10) | 0.0364 (9) | 0.0347 (9) | −0.0129 (7) | 0.0042 (7) | −0.0004 (7) |
C1 | 0.0260 (8) | 0.0371 (10) | 0.0241 (9) | −0.0019 (7) | 0.0069 (7) | −0.0029 (7) |
C2 | 0.0244 (8) | 0.0304 (9) | 0.0238 (9) | 0.0074 (7) | 0.0004 (6) | 0.0003 (7) |
C3 | 0.0296 (9) | 0.0401 (11) | 0.0271 (10) | 0.0077 (8) | 0.0042 (7) | 0.0058 (7) |
C4 | 0.0345 (10) | 0.0468 (12) | 0.0244 (10) | 0.0152 (8) | 0.0025 (8) | 0.0054 (8) |
C5 | 0.0405 (10) | 0.0411 (11) | 0.0265 (10) | 0.0140 (8) | 0.0004 (8) | −0.0043 (8) |
C6 | 0.0378 (10) | 0.0306 (10) | 0.0291 (10) | 0.0065 (8) | 0.0006 (8) | −0.0054 (7) |
C7 | 0.0274 (8) | 0.0260 (8) | 0.0240 (9) | 0.0074 (6) | 0.0022 (6) | −0.0001 (6) |
C8 | 0.0266 (8) | 0.0249 (8) | 0.0285 (9) | 0.0027 (6) | 0.0033 (7) | 0.0001 (7) |
C9 | 0.0232 (8) | 0.0291 (9) | 0.0227 (8) | 0.0038 (6) | 0.0049 (6) | 0.0004 (6) |
C10 | 0.0270 (8) | 0.0299 (9) | 0.0231 (9) | 0.0001 (7) | 0.0022 (7) | −0.0007 (6) |
C11 | 0.0274 (8) | 0.0224 (8) | 0.0219 (8) | −0.0018 (6) | 0.0023 (6) | 0.0004 (6) |
C12 | 0.0275 (8) | 0.0330 (9) | 0.0199 (8) | 0.0056 (7) | 0.0044 (6) | −0.0004 (6) |
C13 | 0.0383 (10) | 0.0391 (10) | 0.0354 (11) | 0.0103 (8) | 0.0145 (8) | 0.0088 (8) |
C14 | 0.0568 (14) | 0.0554 (14) | 0.0310 (11) | 0.0293 (11) | 0.0131 (9) | 0.0131 (9) |
C15 | 0.0444 (13) | 0.0768 (17) | 0.0303 (11) | 0.0316 (11) | −0.0041 (9) | −0.0078 (10) |
C16 | 0.0317 (10) | 0.0670 (15) | 0.0494 (14) | 0.0053 (10) | −0.0066 (9) | −0.0135 (11) |
C17 | 0.0309 (10) | 0.0455 (12) | 0.0336 (11) | 0.0011 (8) | −0.0005 (8) | −0.0013 (8) |
C18 | 0.0259 (8) | 0.0221 (8) | 0.0231 (8) | −0.0041 (6) | 0.0032 (6) | 0.0004 (6) |
C19 | 0.0303 (9) | 0.0297 (9) | 0.0246 (9) | 0.0006 (7) | 0.0052 (7) | 0.0006 (7) |
C20 | 0.0417 (10) | 0.0329 (10) | 0.0272 (9) | −0.0019 (8) | 0.0105 (8) | −0.0017 (7) |
C21 | 0.0508 (12) | 0.0349 (10) | 0.0217 (10) | −0.0075 (8) | 0.0030 (8) | 0.0041 (7) |
C22 | 0.0423 (10) | 0.0276 (9) | 0.0289 (10) | −0.0039 (8) | −0.0041 (8) | 0.0067 (7) |
C23 | 0.0310 (9) | 0.0246 (9) | 0.0277 (9) | −0.0010 (7) | 0.0009 (7) | 0.0015 (7) |
C24 | 0.0885 (17) | 0.0313 (11) | 0.0407 (12) | −0.0116 (10) | 0.0157 (11) | 0.0017 (9) |
C25 | 0.0465 (12) | 0.0630 (15) | 0.0477 (14) | −0.0195 (10) | 0.0099 (10) | −0.0219 (11) |
Geometric parameters (Å, º) top
O1—C2 | 1.377 (2) | C13—C14 | 1.384 (3) |
O1—C1 | 1.381 (2) | C13—H13 | 0.93 |
O2—C1 | 1.215 (2) | C14—C15 | 1.383 (3) |
N1—C8 | 1.388 (2) | C14—H14 | 0.96 (2) |
N1—C24 | 1.453 (2) | C15—C16 | 1.375 (3) |
N1—C25 | 1.462 (2) | C15—H15 | 0.97 (2) |
C1—C9 | 1.444 (2) | C16—C17 | 1.396 (2) |
C2—C3 | 1.392 (2) | C16—H16 | 0.93 |
C2—C7 | 1.392 (2) | C17—H17 | 1.01 (2) |
C3—C4 | 1.386 (3) | C18—C23 | 1.402 (2) |
C3—H3 | 0.96 (2) | C18—C19 | 1.402 (2) |
C4—C5 | 1.390 (3) | C19—C20 | 1.382 (2) |
C4—H4 | 1.01 (2) | C19—H19 | 0.99 (2) |
C5—C6 | 1.373 (3) | C20—C21 | 1.391 (3) |
C5—H5 | 1.05 (2) | C20—H20 | 1.05 (2) |
C6—C7 | 1.415 (2) | C21—C22 | 1.388 (3) |
C6—H6 | 0.93 (2) | C21—H21 | 0.87 (2) |
C7—C8 | 1.461 (2) | C22—C23 | 1.384 (2) |
C8—C9 | 1.376 (2) | C22—H22 | 1.03 (2) |
C9—C10 | 1.484 (2) | C23—H23 | 0.96 (2) |
C10—C11 | 1.339 (2) | C24—H24A | 0.96 |
C10—H10 | 1.00 (2) | C24—H24B | 0.96 |
C11—C18 | 1.484 (2) | C24—H24C | 0.96 |
C11—C12 | 1.490 (2) | C25—H25A | 0.96 |
C12—C17 | 1.395 (2) | C25—H25B | 0.96 |
C12—C13 | 1.398 (2) | C25—H25C | 0.96 |
| | | |
C2—O1—C1 | 120.61 (13) | C15—C14—C13 | 120.5 (2) |
C8—N1—C24 | 122.32 (15) | C15—C14—H14 | 120.0 (13) |
C8—N1—C25 | 120.38 (15) | C13—C14—H14 | 119.4 (13) |
C24—N1—C25 | 114.83 (16) | C16—C15—C14 | 119.47 (18) |
O2—C1—O1 | 115.71 (15) | C16—C15—H15 | 120.9 (12) |
O2—C1—C9 | 125.01 (16) | C14—C15—H15 | 119.6 (12) |
O1—C1—C9 | 119.23 (14) | C15—C16—C17 | 120.8 (2) |
O1—C2—C3 | 115.41 (15) | C15—C16—H16 | 119.6 |
O1—C2—C7 | 121.76 (15) | C17—C16—H16 | 119.6 |
C3—C2—C7 | 122.81 (16) | C12—C17—C16 | 120.1 (2) |
C4—C3—C2 | 119.18 (18) | C12—C17—H17 | 120.7 (10) |
C4—C3—H3 | 123.4 (12) | C16—C17—H17 | 119.3 (10) |
C2—C3—H3 | 117.4 (12) | C23—C18—C19 | 117.84 (15) |
C3—C4—C5 | 119.49 (18) | C23—C18—C11 | 121.43 (15) |
C3—C4—H4 | 120.1 (10) | C19—C18—C11 | 120.70 (14) |
C5—C4—H4 | 120.4 (10) | C20—C19—C18 | 121.20 (16) |
C6—C5—C4 | 120.69 (17) | C20—C19—H19 | 115.8 (11) |
C6—C5—H5 | 122.0 (11) | C18—C19—H19 | 122.9 (11) |
C4—C5—H5 | 117.3 (11) | C19—C20—C21 | 120.22 (18) |
C5—C6—C7 | 121.55 (18) | C19—C20—H20 | 124.2 (11) |
C5—C6—H6 | 114.5 (13) | C21—C20—H20 | 115.6 (11) |
C7—C6—H6 | 123.9 (13) | C22—C21—C20 | 119.31 (18) |
C2—C7—C6 | 116.16 (16) | C22—C21—H21 | 120.6 (14) |
C2—C7—C8 | 118.93 (15) | C20—C21—H21 | 120.1 (14) |
C6—C7—C8 | 124.55 (16) | C23—C22—C21 | 120.60 (17) |
C9—C8—N1 | 123.53 (16) | C23—C22—H22 | 125.5 (12) |
C9—C8—C7 | 118.42 (15) | C21—C22—H22 | 113.9 (12) |
N1—C8—C7 | 117.83 (15) | C22—C23—C18 | 120.81 (17) |
C8—C9—C1 | 120.91 (15) | C22—C23—H23 | 121.2 (11) |
C8—C9—C10 | 125.75 (15) | C18—C23—H23 | 117.9 (11) |
C1—C9—C10 | 113.34 (14) | N1—C24—H24A | 109.5 |
C11—C10—C9 | 126.37 (15) | N1—C24—H24B | 109.5 |
C11—C10—H10 | 116.6 (10) | H24A—C24—H24B | 109.5 |
C9—C10—H10 | 116.9 (10) | N1—C24—H24C | 109.5 |
C10—C11—C18 | 120.95 (14) | H24A—C24—H24C | 109.5 |
C10—C11—C12 | 122.26 (15) | H24B—C24—H24C | 109.5 |
C18—C11—C12 | 116.75 (14) | N1—C25—H25A | 109.5 |
C17—C12—C13 | 118.50 (16) | N1—C25—H25B | 109.5 |
C17—C12—C11 | 120.95 (15) | H25A—C25—H25B | 109.5 |
C13—C12—C11 | 120.48 (15) | N1—C25—H25C | 109.5 |
C14—C13—C12 | 120.66 (19) | H25A—C25—H25C | 109.5 |
C14—C13—H13 | 119.7 | H25B—C25—H25C | 109.5 |
C12—C13—H13 | 119.7 | | |
| | | |
C2—O1—C1—O2 | 177.75 (15) | O1—C1—C9—C10 | −177.73 (13) |
C2—O1—C1—C9 | −4.7 (2) | C8—C9—C10—C11 | −65.1 (2) |
C1—O1—C2—C3 | −174.35 (14) | C1—C9—C10—C11 | 115.26 (18) |
C1—O1—C2—C7 | 3.7 (2) | C9—C10—C11—C18 | 177.26 (15) |
O1—C2—C3—C4 | 176.49 (14) | C9—C10—C11—C12 | −5.3 (3) |
C7—C2—C3—C4 | −1.6 (2) | C10—C11—C12—C17 | 124.64 (19) |
C2—C3—C4—C5 | −1.1 (2) | C18—C11—C12—C17 | −57.8 (2) |
C3—C4—C5—C6 | 1.3 (3) | C10—C11—C12—C13 | −58.4 (2) |
C4—C5—C6—C7 | 1.2 (3) | C18—C11—C12—C13 | 119.20 (17) |
O1—C2—C7—C6 | −174.04 (14) | C17—C12—C13—C14 | −0.5 (3) |
C3—C2—C7—C6 | 3.9 (2) | C11—C12—C13—C14 | −177.56 (17) |
O1—C2—C7—C8 | −0.7 (2) | C12—C13—C14—C15 | −0.5 (3) |
C3—C2—C7—C8 | 177.30 (14) | C13—C14—C15—C16 | 0.6 (3) |
C5—C6—C7—C2 | −3.7 (2) | C14—C15—C16—C17 | 0.4 (3) |
C5—C6—C7—C8 | −176.68 (15) | C13—C12—C17—C16 | 1.4 (3) |
C24—N1—C8—C9 | −33.3 (3) | C11—C12—C17—C16 | 178.45 (17) |
C25—N1—C8—C9 | 127.93 (18) | C15—C16—C17—C12 | −1.4 (3) |
C24—N1—C8—C7 | 141.09 (18) | C10—C11—C18—C23 | −28.2 (2) |
C25—N1—C8—C7 | −57.7 (2) | C12—C11—C18—C23 | 154.15 (15) |
C2—C7—C8—C9 | −1.4 (2) | C10—C11—C18—C19 | 149.57 (16) |
C6—C7—C8—C9 | 171.42 (15) | C12—C11—C18—C19 | −28.0 (2) |
C2—C7—C8—N1 | −176.04 (15) | C23—C18—C19—C20 | 1.2 (2) |
C6—C7—C8—N1 | −3.3 (2) | C11—C18—C19—C20 | −176.70 (15) |
N1—C8—C9—C1 | 174.74 (15) | C18—C19—C20—C21 | −0.3 (3) |
C7—C8—C9—C1 | 0.4 (2) | C19—C20—C21—C22 | −0.2 (3) |
N1—C8—C9—C10 | −4.9 (3) | C20—C21—C22—C23 | −0.2 (3) |
C7—C8—C9—C10 | −179.24 (14) | C21—C22—C23—C18 | 1.1 (3) |
O2—C1—C9—C8 | 179.96 (17) | C19—C18—C23—C22 | −1.6 (2) |
O1—C1—C9—C8 | 2.6 (2) | C11—C18—C23—C22 | 176.29 (15) |
O2—C1—C9—C10 | −0.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 1.01 (2) | 2.54 (2) | 3.550 (2) | 174 (1) |
C23—H23···O2ii | 0.96 (2) | 2.55 (2) | 3.487 (2) | 165 (1) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y−1/2, −z+1/2. |