4-{5-(Di­methyl­amino)-2-[4-(di­methyl­amino)-2-iodo­phenyl­methyl]­phenyl}-(3E)-3-buten-2-one

The title compound, C₂₁H₂₅BrN₂O, was synthesized by the Heck reaction. Its crystal structure shows that there are π–π-stacking interactions between the two aromatic rings of the two neighboring mol­ecules in the unit cell. The C—I bond distance is 2.108 (4) Å and the butene double-bond distance is 1.311 (4) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.103
• Data-to-parameter ratio = 14.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: CAD-4-PC (Enraf-Nonius, 1989); cell refinement: CAD-4-PC; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

4-{5-(dimethylamino)-2-[(4-(dimethylamino)-2 -iodophenyl)methyl]phenyl}-(3E)-3-Buten-2-one

Crystal data

C21H25IN2O	Z = 2
Mr = 448.33	F(000) = 452
Triclinic, P1	Dx = 1.510 Mg m^−3
Hall symbol: -P 1	Melting point: 437-438K K
a = 9.168 (3) Å	Mo Kα radiation, λ = 0.71069 Å
b = 10.884 (1) Å	Cell parameters from 25 reflections
c = 10.969 (2) Å	θ = 0.0–25.0°
α = 84.83 (1)°	µ = 1.63 mm^−1
β = 82.21 (2)°	T = 293 K
γ = 65.51 (2)°	Plate, brown
V = 986.2 (4) Å^3	0.3 × 0.2 × 0.2 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	2963 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω/2θ scans	h = −10→10
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.682, Tmax = 0.721	l = 0→13
3613 measured reflections	5 standard reflections every 300 reflections
3417 independent reflections	intensity decay: 0.0005%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.02P)^2 + 1.98P] where P = (Fo^2 + 2Fc^2)/3
3377 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.97 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. All commercially available reagents were used as supplied. ¹H NMR spectra were obtained from CDCl₃ solution using TMS as an internal standard on a Bruker FC-80 A instrument. Mass spectra (MS) were measured on an HP-5988 A GCMS spectrometer. CHN analyses were performed on a Carlo Erba 1106 elemental analyzer. FT–IR spectra were taken on a Nicolet 179 SXFT-IR spectrophotometer.

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
I1	0.32012 (3)	0.26835 (3)	0.97653 (3)	0.09612 (10)
N1	0.8990 (4)	0.0835 (4)	1.1479 (3)	0.0958 (12)
N2	0.8529 (4)	0.5409 (3)	0.3573 (3)	0.0869 (10)
O1	0.8223 (4)	−0.0984 (3)	0.5422 (3)	0.1048 (11)
C1	1.0574 (5)	0.0737 (4)	1.1539 (4)	0.0904 (13)
H1A	1.0515	0.1501	1.1950	0.136*
H1B	1.1104	0.0723	1.0720	0.136*
H1C	1.1171	−0.0079	1.1987	0.136*
C2	0.8401 (5)	0.0056 (5)	1.2351 (4)	0.1074 (16)
H2A	0.7557	0.0646	1.2913	0.161*
H2B	0.9263	−0.0559	1.2799	0.161*
H2C	0.7987	−0.0446	1.1930	0.161*
C3	0.7987 (4)	0.1759 (4)	1.0673 (3)	0.0702 (10)
C4	0.8456 (4)	0.2650 (4)	0.9901 (3)	0.0738 (11)
H4	0.9454	0.2665	0.9945	0.089*
C5	0.7459 (4)	0.3507 (3)	0.9074 (3)	0.0684 (10)
H5	0.7815	0.4085	0.8571	0.082*
C6	0.5961 (4)	0.3555 (3)	0.8951 (3)	0.0602 (9)
C7	0.5481 (4)	0.2733 (3)	0.9733 (3)	0.0662 (9)
C8	0.6438 (4)	0.1837 (4)	1.0578 (3)	0.0703 (10)
H8	0.6049	0.1284	1.1087	0.084*
C9	0.4930 (4)	0.4572 (4)	0.8025 (3)	0.0698 (10)
H9A	0.4140	0.4266	0.7823	0.084*
H9B	0.4348	0.5434	0.8411	0.084*
C10	0.5877 (4)	0.4775 (3)	0.6851 (3)	0.0622 (9)
C11	0.6601 (4)	0.3758 (3)	0.5967 (3)	0.0600 (9)
C12	0.7471 (4)	0.3991 (3)	0.4904 (3)	0.0629 (9)
H12	0.7926	0.3323	0.4325	0.075*
C13	0.7693 (4)	0.5182 (3)	0.4666 (3)	0.0642 (9)
C14	0.7001 (4)	0.6166 (3)	0.5554 (3)	0.0689 (10)
H14	0.7136	0.6971	0.5435	0.083*
C15	0.6120 (4)	0.5944 (3)	0.6606 (3)	0.0676 (10)
H15	0.5667	0.6618	0.7179	0.081*
C16	0.8916 (4)	0.6558 (4)	0.3420 (4)	0.0800 (12)
H16A	0.7946	0.7364	0.3546	0.120*
H16B	0.9430	0.6590	0.2602	0.120*
H16C	0.9632	0.6493	0.4009	0.120*
C17	0.9421 (5)	0.4316 (4)	0.2774 (4)	0.0879 (13)
H17A	1.0231	0.3609	0.3204	0.132*
H17B	0.9929	0.4629	0.2066	0.132*
H17C	0.8704	0.3976	0.2515	0.132*
C18	0.6433 (4)	0.2480 (3)	0.6166 (3)	0.0639 (9)
H18	0.5523	0.2492	0.6665	0.077*
C19	0.7429 (4)	0.1313 (3)	0.5716 (3)	0.0692 (10)
H19	0.8352	0.1294	0.5232	0.083*
C20	0.7237 (5)	0.0044 (4)	0.5898 (3)	0.0754 (11)
C21	0.5803 (5)	−0.0020 (4)	0.6708 (5)	0.1036 (15)
H21A	0.5956	−0.0946	0.6856	0.155*
H21B	0.4846	0.0463	0.6305	0.155*
H21C	0.5694	0.0383	0.7477	0.155*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.07575 (13)	0.1258 (2)	0.0981 (2)	−0.05593 (12)	−0.00825 (13)	0.01221 (15)
N1	0.0807 (18)	0.107 (2)	0.091 (2)	−0.0339 (17)	−0.0151 (17)	0.0260 (19)
N2	0.106 (2)	0.0722 (17)	0.077 (2)	−0.0377 (15)	0.0179 (17)	−0.0105 (15)
O1	0.130 (2)	0.0638 (14)	0.107 (2)	−0.0330 (15)	0.0177 (18)	−0.0155 (14)
C1	0.085 (2)	0.082 (2)	0.097 (3)	−0.026 (2)	−0.024 (2)	0.006 (2)
C2	0.100 (3)	0.119 (3)	0.093 (3)	−0.040 (2)	−0.019 (2)	0.036 (2)
C3	0.0695 (18)	0.0708 (19)	0.065 (2)	−0.0252 (16)	−0.0001 (16)	−0.0033 (16)
C4	0.0621 (17)	0.085 (2)	0.074 (2)	−0.0310 (16)	−0.0040 (16)	0.0037 (18)
C5	0.0652 (17)	0.0677 (18)	0.071 (2)	−0.0291 (14)	0.0018 (16)	0.0007 (16)
C6	0.0567 (15)	0.0603 (16)	0.0592 (18)	−0.0210 (13)	0.0037 (14)	−0.0099 (14)
C7	0.0625 (16)	0.0672 (18)	0.070 (2)	−0.0291 (14)	0.0042 (16)	−0.0093 (16)
C8	0.0695 (18)	0.0707 (19)	0.068 (2)	−0.0290 (15)	0.0034 (16)	−0.0028 (16)
C9	0.0635 (18)	0.0659 (19)	0.067 (2)	−0.0148 (15)	0.0005 (16)	−0.0083 (16)
C10	0.0583 (16)	0.0587 (17)	0.0602 (18)	−0.0136 (14)	−0.0080 (14)	−0.0045 (15)
C11	0.0592 (15)	0.0573 (16)	0.0590 (18)	−0.0177 (13)	−0.0128 (14)	−0.0013 (14)
C12	0.0656 (17)	0.0546 (17)	0.0595 (18)	−0.0154 (14)	−0.0037 (15)	−0.0074 (14)
C13	0.0643 (17)	0.0590 (17)	0.0623 (19)	−0.0186 (14)	−0.0071 (15)	−0.0007 (15)
C14	0.0777 (19)	0.0542 (17)	0.067 (2)	−0.0198 (15)	−0.0074 (17)	−0.0012 (15)
C15	0.0733 (19)	0.0548 (17)	0.0634 (19)	−0.0139 (15)	−0.0069 (16)	−0.0080 (15)
C16	0.086 (2)	0.072 (2)	0.077 (2)	−0.0310 (17)	0.0000 (19)	0.0019 (18)
C17	0.096 (2)	0.077 (2)	0.080 (2)	−0.0302 (19)	0.014 (2)	−0.011 (2)
C18	0.0689 (17)	0.0618 (17)	0.0591 (18)	−0.0241 (14)	−0.0089 (15)	−0.0025 (15)
C19	0.0767 (19)	0.0613 (18)	0.064 (2)	−0.0235 (15)	−0.0041 (16)	−0.0017 (16)
C20	0.091 (2)	0.0613 (19)	0.070 (2)	−0.0273 (17)	−0.0056 (18)	−0.0046 (17)
C21	0.093 (3)	0.0831 (12)	0.072 (4)	−0.031 (12)	0.0011 (13)	−0.0038 (12)

Geometric parameters (Å, º)

I1—C7	2.108 (4)	C9—H9B	0.9700
N1—C3	1.390 (5)	C10—C15	1.378 (5)
N1—C2	1.421 (6)	C10—C11	1.420 (4)
N1—C1	1.422 (5)	C11—C12	1.387 (5)
N2—C13	1.393 (4)	C11—C18	1.456 (5)
N2—C16	1.425 (5)	C12—C13	1.390 (5)
N2—C17	1.428 (5)	C12—H12	0.9300
O1—C20	1.217 (4)	C13—C14	1.398 (5)
C1—H1A	0.9600	C14—C15	1.379 (5)
C1—H1B	0.9600	C14—H14	0.9300
C1—H1C	0.9600	C15—H15	0.9300
C2—H2A	0.9600	C16—H16A	0.9600
C2—H2B	0.9600	C16—H16B	0.9600
C2—H2C	0.9600	C16—H16C	0.9600
C3—C4	1.392 (5)	C17—H17A	0.9600
C3—C8	1.405 (5)	C17—H17B	0.9600
C4—C5	1.377 (5)	C17—H17C	0.9600
C4—H4	0.9300	C18—C19	1.311 (4)
C5—C6	1.377 (5)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.456 (5)
C6—C7	1.347 (5)	C19—H19	0.9300
C6—C9	1.530 (4)	C20—C21	1.507 (6)
C7—C8	1.389 (5)	C21—H21A	0.9600
C8—H8	0.9300	C21—H21B	0.9600
C9—C10	1.506 (5)	C21—H21C	0.9600
C9—H9A	0.9700
C3—N1—C2	120.6 (4)	C11—C10—C9	121.6 (3)
C3—N1—C1	121.1 (4)	C12—C11—C10	119.4 (3)
C2—N1—C1	118.0 (3)	C12—C11—C18	120.0 (3)
C13—N2—C16	120.3 (3)	C10—C11—C18	120.6 (3)
C13—N2—C17	119.3 (3)	C11—C12—C13	122.7 (3)
C16—N2—C17	117.6 (3)	C11—C12—H12	118.6
N1—C1—H1A	109.5	C13—C12—H12	118.6
N1—C1—H1B	109.5	C12—C13—N2	121.6 (3)
H1A—C1—H1B	109.5	C12—C13—C14	117.4 (3)
N1—C1—H1C	109.5	N2—C13—C14	121.0 (3)
H1A—C1—H1C	109.5	C15—C14—C13	120.1 (3)
H1B—C1—H1C	109.5	C15—C14—H14	120.0
N1—C2—H2A	109.5	C13—C14—H14	120.0
N1—C2—H2B	109.5	C10—C15—C14	123.3 (3)
H2A—C2—H2B	109.5	C10—C15—H15	118.3
N1—C2—H2C	109.5	C14—C15—H15	118.3
H2A—C2—H2C	109.5	N2—C16—H16A	109.5
H2B—C2—H2C	109.5	N2—C16—H16B	109.5
N1—C3—C4	122.5 (3)	H16A—C16—H16B	109.5
N1—C3—C8	121.7 (3)	N2—C16—H16C	109.5
C4—C3—C8	115.9 (3)	H16A—C16—H16C	109.5
C5—C4—C3	120.8 (4)	H16B—C16—H16C	109.5
C5—C4—H4	119.6	N2—C17—H17A	109.5
C3—C4—H4	119.6	N2—C17—H17B	109.5
C4—C5—C6	123.4 (3)	H17A—C17—H17B	109.5
C4—C5—H5	118.3	N2—C17—H17C	109.5
C6—C5—H5	118.3	H17A—C17—H17C	109.5
C7—C6—C5	115.7 (3)	H17B—C17—H17C	109.5
C7—C6—C9	124.9 (3)	C19—C18—C11	126.9 (3)
C5—C6—C9	119.3 (3)	C19—C18—H18	116.5
C6—C7—C8	123.4 (3)	C11—C18—H18	116.5
C6—C7—I1	122.6 (2)	C18—C19—C20	126.7 (3)
C8—C7—I1	114.0 (3)	C18—C19—H19	116.7
C7—C8—C3	120.7 (3)	C20—C19—H19	116.7
C7—C8—H8	119.7	O1—C20—C19	121.6 (4)
C3—C8—H8	119.7	O1—C20—C21	118.5 (4)
C10—C9—C6	114.1 (3)	C19—C20—C21	119.9 (3)
C10—C9—H9A	108.7	C20—C21—H21A	109.5
C6—C9—H9A	108.7	C20—C21—H21B	109.5
C10—C9—H9B	108.7	H21A—C21—H21B	109.5
C6—C9—H9B	108.7	C20—C21—H21C	109.5
H9A—C9—H9B	107.6	H21A—C21—H21C	109.5
C15—C10—C11	117.1 (3)	H21B—C21—H21C	109.5
C15—C10—C9	121.3 (3)