4-(N,N-Di­methyl­amino)-3-(2,2-di­phenyl­ethenyl)­coumarin

In the title compound, C₂₅H₂₁NO₂, 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...O interactions and van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	Block, yellow
Z = 4	0.44 × 0.38 × 0.26 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.141	w = 1/[σ^2(Fo^2) + (0.0397P)^2] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (2)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2^i	1.01 (2)	2.54 (2)	3.550 (2)	174 (1)
C23—H23···O2^ii	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.