(2E,2′E)-1,1′-([1,1′-Biphen­yl]-4,4′-di­yl)bis­[3-(di­meth­yl­amino)­prop-2-en-1-one]

The title compound, C₂₂H₂₄N₂O₂, crystallizes in space group P2₁/n. The mol­ecular structure is almost planar except for a tilt of the phenyl rings. The allyl groups on both ends exhibit the trans-form and the connected N atoms show sp² character. The mol­ecules are stacked and assembled along the c-axis direction by C—H...π inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.063
• wR factor = 0.154
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C22 H24 N2 O2
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     12.584 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.496 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
                1  0  5,   7  6  6,
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check
               13  2 13,

Alert level G
PLAT484_ALERT_4_G Round D-H..A Angle Rep for C21      ..O2       .        152 Degree
PLAT484_ALERT_4_G Round D-H..A Angle Rep for C22      ..O1       .        154 Degree
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
               -1  0  1,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600       1014 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
                1  0  5,
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.5 Low
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       2.32 Note
              Predicted wR2: Based on SigI   2  6.63 or SHELX Weight 14.68       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

(2E,2'E)-1,1'-([1,1'-Biphenyl]-4,4'-diyl)bis[3-(dimethylamino)prop-2-en-1-one]

Crystal data

C22H24N2O2	F(000) = 744
Mr = 348.43	Dx = 1.311 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
a = 15.862 (1) Å	Cell parameters from 2411 reflections
b = 6.0503 (4) Å	θ = 3.0–29.0°
c = 19.0640 (12) Å	µ = 0.08 mm^−1
β = 105.287 (3)°	T = 90 K
V = 1764.8 (2) Å^3	Block, yellow
Z = 4	0.40 × 0.20 × 0.20 mm

Data collection

Bruker PHOTON II CPAD diffractometer	3539 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.076
φ and ω scans	θmax = 31.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −22→23
Tmin = 0.669, Tmax = 0.746	k = −8→8
21542 measured reflections	l = −27→26
4738 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.0561P)^2 + 0.8647P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
4738 reflections	Δρmax = 0.31 e Å^−3
239 parameters	Δρmin = −0.25 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

All hydrogen atoms were fixed geometrically and refined using a riding-model approximation with C—H = 0.95 (for phenyl and allyl) and 0.98 (for methyl) Å.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.44366 (8)	0.0656 (2)	0.82473 (8)	0.0251 (3)
O2	−0.18571 (8)	−0.6345 (2)	0.92406 (8)	0.0260 (3)
C1	0.08648 (11)	−0.3027 (3)	0.88219 (9)	0.0172 (3)
C2	0.42078 (11)	−0.1318 (3)	0.82155 (9)	0.0183 (4)
N1	−0.35165 (9)	−0.1752 (2)	0.97342 (8)	0.0206 (3)
N2	0.60934 (9)	−0.3981 (3)	0.77673 (9)	0.0216 (3)
C3	0.33358 (11)	−0.1860 (3)	0.83472 (9)	0.0164 (3)
C4	−0.07530 (11)	−0.3830 (3)	0.91419 (9)	0.0182 (4)
C5	−0.16200 (11)	−0.4379 (3)	0.92887 (10)	0.0194 (4)
C6	0.23300 (11)	−0.4325 (3)	0.87142 (9)	0.0184 (4)
H6	0.220473	−0.575129	0.886905	0.022*
C7	0.17109 (11)	−0.2637 (3)	0.86495 (9)	0.0171 (4)
C8	0.47315 (11)	−0.3113 (3)	0.80669 (10)	0.0190 (4)
H8	0.454442	−0.460179	0.807627	0.023*
C9	0.04331 (11)	−0.1358 (3)	0.90959 (10)	0.0194 (4)
H9	0.069054	0.006774	0.918150	0.023*
C10	−0.29110 (11)	−0.3106 (3)	0.96087 (9)	0.0197 (4)
H10	−0.302961	−0.463891	0.963229	0.024*
C11	0.19194 (11)	−0.0561 (3)	0.84176 (10)	0.0188 (4)
H11	0.150491	0.060452	0.835705	0.023*
C12	−0.21424 (11)	−0.2595 (3)	0.94506 (10)	0.0204 (4)
H12	−0.195669	−0.110271	0.944727	0.024*
C13	0.55029 (11)	−0.2624 (3)	0.79123 (10)	0.0197 (4)
H13	0.563685	−0.109429	0.790785	0.024*
C14	0.27188 (11)	−0.0173 (3)	0.82748 (9)	0.0182 (4)
H14	0.284837	0.125692	0.812585	0.022*
C15	0.04694 (11)	−0.5114 (3)	0.87134 (10)	0.0206 (4)
H15	0.074488	−0.627754	0.852269	0.025*
C16	0.31225 (11)	−0.3953 (3)	0.85566 (9)	0.0176 (4)
H16	0.352524	−0.513573	0.859146	0.021*
C17	−0.03656 (11)	−0.1741 (3)	0.92460 (10)	0.0197 (4)
H17	−0.065153	−0.056678	0.942160	0.024*
C18	−0.03162 (11)	−0.5510 (3)	0.88793 (10)	0.0193 (4)
H18	−0.056200	−0.695105	0.881307	0.023*
C19	−0.42660 (11)	−0.2587 (3)	0.99574 (10)	0.0231 (4)
H19	−0.425634	−0.420614	0.995747	0.035*
H19A	−0.480571	−0.206431	0.961739	0.035*
H19B	−0.424069	−0.205172	1.044775	0.035*
C20	0.68514 (12)	−0.3137 (3)	0.75587 (11)	0.0259 (4)
H20	0.683659	−0.151744	0.755483	0.039*
H20A	0.684187	−0.367920	0.707229	0.039*
H20B	0.738614	−0.364478	0.790844	0.039*
C21	−0.34611 (12)	0.0646 (3)	0.96831 (11)	0.0248 (4)
H21	−0.334516	0.129235	1.017057	0.037*
H21A	−0.401469	0.122254	0.937915	0.037*
H21B	−0.298604	0.103377	0.946522	0.037*
C22	0.60316 (12)	−0.6375 (3)	0.78032 (11)	0.0239 (4)
H22	0.553718	−0.677418	0.799595	0.036*
H22A	0.657287	−0.696557	0.812301	0.036*
H22B	0.594317	−0.699911	0.731468	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0229 (6)	0.0164 (6)	0.0391 (8)	−0.0025 (5)	0.0138 (6)	−0.0007 (6)
O2	0.0243 (7)	0.0191 (7)	0.0391 (8)	−0.0041 (5)	0.0161 (6)	−0.0028 (6)
C1	0.0160 (8)	0.0166 (8)	0.0198 (8)	0.0012 (7)	0.0060 (7)	0.0014 (7)
C2	0.0168 (8)	0.0191 (9)	0.0206 (8)	−0.0004 (7)	0.0076 (7)	−0.0003 (7)
N1	0.0188 (7)	0.0179 (8)	0.0273 (8)	−0.0018 (6)	0.0098 (6)	−0.0017 (6)
N2	0.0194 (7)	0.0180 (8)	0.0314 (8)	−0.0005 (6)	0.0135 (7)	0.0007 (6)
C3	0.0169 (8)	0.0160 (8)	0.0171 (8)	−0.0007 (7)	0.0057 (7)	−0.0006 (7)
C4	0.0178 (8)	0.0183 (9)	0.0201 (8)	0.0005 (7)	0.0075 (7)	0.0015 (7)
C5	0.0203 (8)	0.0194 (9)	0.0201 (8)	−0.0007 (7)	0.0083 (7)	0.0004 (7)
C6	0.0189 (8)	0.0141 (8)	0.0240 (9)	0.0003 (7)	0.0089 (7)	0.0005 (7)
C7	0.0186 (8)	0.0147 (8)	0.0194 (8)	−0.0002 (7)	0.0073 (7)	−0.0010 (7)
C8	0.0170 (8)	0.0187 (9)	0.0237 (9)	−0.0014 (7)	0.0094 (7)	−0.0001 (7)
C9	0.0205 (8)	0.0141 (8)	0.0251 (9)	−0.0024 (7)	0.0085 (7)	−0.0018 (7)
C10	0.0207 (8)	0.0176 (9)	0.0216 (9)	−0.0004 (7)	0.0068 (7)	−0.0006 (7)
C11	0.0166 (8)	0.0151 (8)	0.0250 (9)	0.0023 (7)	0.0056 (7)	−0.0012 (7)
C12	0.0210 (8)	0.0171 (9)	0.0257 (9)	−0.0017 (7)	0.0109 (7)	−0.0003 (7)
C13	0.0204 (8)	0.0158 (8)	0.0246 (9)	−0.0007 (7)	0.0087 (7)	0.0000 (7)
C14	0.0198 (8)	0.0145 (8)	0.0212 (8)	−0.0002 (7)	0.0071 (7)	0.0010 (7)
C15	0.0209 (8)	0.0151 (8)	0.0284 (9)	0.0016 (7)	0.0110 (8)	−0.0020 (7)
C16	0.0171 (8)	0.0155 (8)	0.0210 (8)	0.0022 (7)	0.0065 (7)	0.0003 (7)
C17	0.0208 (8)	0.0166 (9)	0.0248 (9)	−0.0003 (7)	0.0117 (7)	−0.0043 (7)
C18	0.0180 (8)	0.0143 (8)	0.0259 (9)	−0.0016 (7)	0.0064 (7)	0.0004 (7)
C19	0.0194 (8)	0.0239 (10)	0.0292 (10)	−0.0010 (7)	0.0120 (8)	0.0022 (8)
C20	0.0203 (9)	0.0246 (10)	0.0375 (11)	−0.0010 (8)	0.0160 (8)	0.0029 (8)
C21	0.0267 (9)	0.0192 (9)	0.0315 (10)	0.0013 (8)	0.0132 (8)	0.0011 (8)
C22	0.0237 (9)	0.0188 (9)	0.0324 (10)	0.0022 (7)	0.0132 (8)	0.0009 (8)

Geometric parameters (Å, º)

O1—C2	1.245 (2)	C9—H9	0.9500
O2—C5	1.243 (2)	C10—C12	1.366 (2)
C1—C9	1.396 (2)	C10—H10	0.9500
C1—C15	1.401 (2)	C11—C14	1.385 (2)
C1—C7	1.482 (2)	C11—H11	0.9500
C2—C8	1.440 (2)	C12—H12	0.9500
C2—C3	1.506 (2)	C13—H13	0.9500
N1—C10	1.331 (2)	C14—H14	0.9500
N1—C19	1.455 (2)	C15—C18	1.385 (2)
N1—C21	1.458 (2)	C15—H15	0.9500
N2—C13	1.329 (2)	C16—H16	0.9500
N2—C22	1.455 (2)	C17—H17	0.9500
N2—C20	1.455 (2)	C18—H18	0.9500
C3—C14	1.395 (2)	C19—H19	0.9800
C3—C16	1.396 (2)	C19—H19A	0.9800
C4—C18	1.395 (2)	C19—H19B	0.9800
C4—C17	1.397 (2)	C20—H20	0.9800
C4—C5	1.511 (2)	C20—H20A	0.9800
C5—C12	1.443 (2)	C20—H20B	0.9800
C6—C16	1.386 (2)	C21—H21	0.9800
C6—C7	1.399 (2)	C21—H21A	0.9800
C6—H6	0.9500	C21—H21B	0.9800
C7—C11	1.400 (2)	C22—H22	0.9800
C8—C13	1.364 (2)	C22—H22A	0.9800
C8—H8	0.9500	C22—H22B	0.9800
C9—C17	1.390 (2)
C9—C1—C15	117.55 (15)	N2—C13—C8	129.23 (17)
C9—C1—C7	122.00 (16)	N2—C13—H13	115.4
C15—C1—C7	120.45 (15)	C8—C13—H13	115.4
O1—C2—C8	123.86 (15)	C11—C14—C3	120.76 (16)
O1—C2—C3	118.00 (15)	C11—C14—H14	119.6
C8—C2—C3	118.14 (15)	C3—C14—H14	119.6
C10—N1—C19	121.53 (15)	C18—C15—C1	121.12 (16)
C10—N1—C21	122.76 (15)	C18—C15—H15	119.4
C19—N1—C21	115.68 (14)	C1—C15—H15	119.4
C13—N2—C22	123.09 (15)	C6—C16—C3	120.76 (16)
C13—N2—C20	121.23 (15)	C6—C16—H16	119.6
C22—N2—C20	115.68 (15)	C3—C16—H16	119.6
C14—C3—C16	118.36 (15)	C9—C17—C4	120.82 (16)
C14—C3—C2	118.40 (15)	C9—C17—H17	119.6
C16—C3—C2	123.21 (15)	C4—C17—H17	119.6
C18—C4—C17	117.95 (15)	C15—C18—C4	121.20 (16)
C18—C4—C5	117.96 (16)	C15—C18—H18	119.4
C17—C4—C5	124.09 (15)	C4—C18—H18	119.4
O2—C5—C12	123.49 (16)	N1—C19—H19	109.5
O2—C5—C4	117.97 (16)	N1—C19—H19A	109.5
C12—C5—C4	118.50 (15)	H19—C19—H19A	109.5
C16—C6—C7	121.20 (16)	N1—C19—H19B	109.5
C16—C6—H6	119.4	H19—C19—H19B	109.5
C7—C6—H6	119.4	H19A—C19—H19B	109.5
C6—C7—C11	117.64 (15)	N2—C20—H20	109.5
C6—C7—C1	121.32 (15)	N2—C20—H20A	109.5
C11—C7—C1	121.04 (15)	H20—C20—H20A	109.5
C13—C8—C2	118.39 (16)	N2—C20—H20B	109.5
C13—C8—H8	120.8	H20—C20—H20B	109.5
C2—C8—H8	120.8	H20A—C20—H20B	109.5
C17—C9—C1	121.34 (16)	N1—C21—H21	109.5
C17—C9—H9	119.3	N1—C21—H21A	109.5
C1—C9—H9	119.3	H21—C21—H21A	109.5
N1—C10—C12	128.94 (17)	N1—C21—H21B	109.5
N1—C10—H10	115.5	H21—C21—H21B	109.5
C12—C10—H10	115.5	H21A—C21—H21B	109.5
C14—C11—C7	121.23 (16)	N2—C22—H22	109.5
C14—C11—H11	119.4	N2—C22—H22A	109.5
C7—C11—H11	119.4	H22—C22—H22A	109.5
C10—C12—C5	118.29 (16)	N2—C22—H22B	109.5
C10—C12—H12	120.9	H22—C22—H22B	109.5
C5—C12—H12	120.9	H22A—C22—H22B	109.5
O1—C2—C3—C14	19.5 (2)	C1—C7—C11—C14	178.24 (16)
C8—C2—C3—C14	−161.06 (16)	N1—C10—C12—C5	−175.95 (17)
O1—C2—C3—C16	−158.78 (17)	O2—C5—C12—C10	4.7 (3)
C8—C2—C3—C16	20.7 (3)	C4—C5—C12—C10	−177.69 (16)
C18—C4—C5—O2	7.3 (2)	C22—N2—C13—C8	−4.7 (3)
C17—C4—C5—O2	−173.35 (18)	C20—N2—C13—C8	175.17 (19)
C18—C4—C5—C12	−170.47 (16)	C2—C8—C13—N2	179.18 (18)
C17—C4—C5—C12	8.9 (3)	C7—C11—C14—C3	1.0 (3)
C16—C6—C7—C11	0.2 (3)	C16—C3—C14—C11	0.9 (3)
C16—C6—C7—C1	−179.64 (16)	C2—C3—C14—C11	−177.45 (16)
C9—C1—C7—C6	149.01 (17)	C9—C1—C15—C18	−0.7 (3)
C15—C1—C7—C6	−30.9 (3)	C7—C1—C15—C18	179.29 (16)
C9—C1—C7—C11	−30.8 (3)	C7—C6—C16—C3	1.8 (3)
C15—C1—C7—C11	149.25 (18)	C14—C3—C16—C6	−2.3 (3)
O1—C2—C8—C13	−3.7 (3)	C2—C3—C16—C6	175.97 (16)
C3—C2—C8—C13	176.87 (16)	C1—C9—C17—C4	1.4 (3)
C15—C1—C9—C17	−0.9 (3)	C18—C4—C17—C9	−0.4 (3)
C7—C1—C9—C17	179.15 (16)	C5—C4—C17—C9	−179.73 (16)
C19—N1—C10—C12	−174.60 (18)	C1—C15—C18—C4	1.7 (3)
C21—N1—C10—C12	3.2 (3)	C17—C4—C18—C15	−1.2 (3)
C6—C7—C11—C14	−1.6 (3)	C5—C4—C18—C15	178.21 (16)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C1/C9/C17/C4/C18/C15 and C3/C14/C11/C7/C6/C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21B···O2^i	0.98	2.51	3.410 (2)	152
C22—H22···O1^ii	0.98	2.48	3.387 (2)	154
C21—H21···Cg2^iii	0.98	2.60	3.538 (2)	160
C22—H22B···Cg1^iv	0.98	2.70	3.608 (2)	154

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x, −y, −z+2; (iv) −x+1/2, y−1/2, −z+3/2.