2-(4-Amino­phen­yl)-3-[3,4-bis­(pyridin-2-ylmeth­oxy)phen­yl]acrylo­nitrile

The crystal structure of C₂₇H₂₂N₄O₂ is characterized by N—H...N hydrogen bonds, which connect the mol­ecules into zigzag chains running along the b-axis direction. The central ring subtends dihedral angles of 17.89 (6)° with the amino­phenyl ring and of 8.75 (9) and 28.77 (7)° with the two pyridyl rings.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.116
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C12 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H26      ..N2       .       2.65 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.709 Check

Alert level G
PLAT230_ALERT_2_G Hirshfeld Test Diff for   C32      --C33       .        6.7 s.u.
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2-(4-Aminophenyl)-3-[3,4-bis(pyridin-2-ylmethoxy)phenyl]acrylonitrile

Crystal data

C27H22N4O2	F(000) = 912
Mr = 434.49	Dx = 1.276 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0233 (15) Å	Cell parameters from 4649 reflections
b = 16.877 (3) Å	θ = 2.4–24.8°
c = 17.013 (3) Å	µ = 0.08 mm^−1
β = 101.021 (2)°	T = 296 K
V = 2261.2 (7) Å^3	Block, yellow
Z = 4	0.21 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD area detector diffractometer	3016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 25.5°, θmin = 1.7°
phi and ω scans	h = −9→9
16528 measured reflections	k = −20→20
4222 independent reflections	l = −20→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0544P)^2 + 0.1757P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
4222 reflections	Δρmax = 0.13 e Å^−3
306 parameters	Δρmin = −0.12 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 H-atom positions were taken from a Fourier map. The H atoms were refined using a riding model with U_iso(H) = 1.2U_eq(C,N).

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

	x	y	z	Uiso*/Ueq
O1	0.49999 (13)	0.35393 (6)	0.60726 (6)	0.0624 (3)
O2	0.64442 (13)	0.43936 (6)	0.72240 (6)	0.0640 (3)
N1	0.5073 (2)	0.18016 (8)	0.49938 (9)	0.0793 (4)
N2	0.9308 (2)	0.45055 (9)	0.90889 (9)	0.0839 (5)
N3	0.08360 (19)	0.41255 (8)	0.36157 (8)	0.0721 (4)
N4	−0.3243 (2)	0.75632 (11)	0.17390 (10)	0.0807 (5)
H4B	−0.383 (3)	0.7318 (13)	0.1266 (14)	0.114 (8)*
H4A	−0.276 (3)	0.8029 (14)	0.1678 (13)	0.115 (8)*
C1	0.44974 (17)	0.43157 (8)	0.60235 (8)	0.0484 (3)
C2	0.53138 (17)	0.47891 (8)	0.66594 (8)	0.0502 (3)
C3	0.49239 (19)	0.55817 (9)	0.66679 (9)	0.0560 (4)
H3	0.545197	0.590099	0.708799	0.067*
C4	0.37400 (19)	0.59051 (9)	0.60481 (8)	0.0555 (4)
H4	0.349164	0.644269	0.605985	0.067*
C5	0.29154 (17)	0.54486 (8)	0.54107 (8)	0.0484 (3)
C6	0.33223 (17)	0.46381 (8)	0.54156 (8)	0.0501 (4)
H6	0.278638	0.431542	0.500006	0.060*
C11	0.4137 (2)	0.30045 (9)	0.55064 (9)	0.0644 (4)
H11A	0.415632	0.318992	0.496858	0.077*
H11B	0.296336	0.295468	0.556604	0.077*
C12	0.50242 (19)	0.22186 (9)	0.56499 (9)	0.0592 (4)
C13	0.5746 (3)	0.19608 (10)	0.64029 (11)	0.0829 (6)
H13	0.564635	0.226012	0.685047	0.099*
C14	0.6619 (3)	0.12559 (12)	0.64889 (13)	0.0966 (7)
H14	0.713511	0.107670	0.699380	0.116*
C15	0.6716 (3)	0.08249 (12)	0.58249 (15)	0.1040 (7)
H15	0.731751	0.035105	0.586148	0.125*
C16	0.5897 (3)	0.11113 (13)	0.50989 (14)	0.1060 (7)
H16	0.591819	0.080287	0.464790	0.127*
C21	0.7269 (2)	0.47956 (9)	0.79186 (9)	0.0609 (4)
H21A	0.643897	0.504435	0.818532	0.073*
H21B	0.801109	0.520361	0.777763	0.073*
C22	0.82829 (19)	0.41938 (9)	0.84601 (8)	0.0566 (4)
C23	0.8152 (2)	0.33945 (10)	0.83217 (10)	0.0700 (5)
H23	0.742020	0.319653	0.787431	0.084*
C24	0.9128 (3)	0.28889 (11)	0.88595 (12)	0.0837 (5)
H24	0.908267	0.234429	0.877454	0.100*
C25	1.0158 (3)	0.31990 (13)	0.95159 (12)	0.0909 (6)
H25	1.080498	0.287013	0.989461	0.109*
C26	1.0221 (3)	0.39952 (14)	0.96067 (12)	0.1004 (7)
H26	1.093962	0.420198	1.005379	0.120*
C31	0.17363 (17)	0.58435 (8)	0.47739 (8)	0.0517 (4)
H31	0.157669	0.637714	0.487389	0.062*
C32	0.08303 (17)	0.55909 (8)	0.40689 (8)	0.0482 (3)
C33	0.08525 (18)	0.47669 (9)	0.38329 (9)	0.0537 (4)
C34	−0.02236 (17)	0.61078 (8)	0.34649 (8)	0.0491 (3)
C35	−0.0004 (2)	0.69284 (9)	0.34669 (9)	0.0625 (4)
H35	0.082626	0.715972	0.385550	0.075*
C36	−0.0996 (2)	0.74018 (9)	0.29030 (10)	0.0697 (5)
H36	−0.083483	0.794767	0.292461	0.084*
C37	−0.2235 (2)	0.70805 (9)	0.23018 (9)	0.0601 (4)
C38	−0.24557 (19)	0.62686 (9)	0.22986 (9)	0.0609 (4)
H38	−0.328422	0.603694	0.190933	0.073*
C39	−0.14660 (19)	0.57983 (9)	0.28634 (9)	0.0565 (4)
H39	−0.163616	0.525305	0.284117	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0689 (7)	0.0464 (6)	0.0622 (6)	0.0023 (5)	−0.0119 (5)	−0.0040 (5)
O2	0.0697 (7)	0.0587 (6)	0.0540 (6)	0.0053 (5)	−0.0127 (5)	−0.0048 (5)
N1	0.0970 (11)	0.0676 (9)	0.0737 (9)	0.0127 (8)	0.0175 (8)	−0.0085 (8)
N2	0.0964 (11)	0.0797 (10)	0.0616 (9)	0.0045 (8)	−0.0206 (8)	−0.0027 (7)
N3	0.0823 (10)	0.0548 (8)	0.0724 (9)	0.0021 (7)	−0.0020 (7)	−0.0032 (7)
N4	0.0973 (12)	0.0680 (10)	0.0690 (10)	0.0147 (9)	−0.0039 (9)	0.0166 (8)
C1	0.0481 (8)	0.0462 (8)	0.0500 (8)	−0.0017 (6)	0.0071 (6)	0.0014 (6)
C2	0.0483 (8)	0.0537 (9)	0.0462 (8)	−0.0004 (7)	0.0033 (6)	0.0021 (6)
C3	0.0580 (9)	0.0552 (9)	0.0515 (8)	−0.0027 (7)	0.0020 (7)	−0.0073 (7)
C4	0.0599 (9)	0.0491 (8)	0.0564 (9)	0.0032 (7)	0.0086 (7)	−0.0023 (7)
C5	0.0466 (8)	0.0514 (8)	0.0475 (8)	−0.0001 (6)	0.0101 (6)	0.0023 (6)
C6	0.0502 (8)	0.0508 (8)	0.0469 (8)	−0.0024 (6)	0.0031 (7)	−0.0013 (6)
C11	0.0672 (10)	0.0542 (9)	0.0643 (10)	−0.0010 (8)	−0.0063 (8)	−0.0083 (7)
C12	0.0614 (10)	0.0494 (9)	0.0646 (10)	−0.0062 (7)	0.0063 (8)	−0.0049 (7)
C13	0.1142 (16)	0.0580 (11)	0.0711 (12)	0.0086 (10)	0.0041 (11)	0.0004 (8)
C14	0.1231 (18)	0.0708 (13)	0.0920 (15)	0.0152 (12)	0.0106 (13)	0.0205 (11)
C15	0.1274 (19)	0.0717 (13)	0.1205 (19)	0.0357 (13)	0.0428 (16)	0.0181 (13)
C16	0.144 (2)	0.0806 (14)	0.0999 (16)	0.0316 (14)	0.0405 (15)	−0.0108 (12)
C21	0.0706 (10)	0.0601 (9)	0.0474 (8)	0.0004 (8)	−0.0008 (7)	−0.0050 (7)
C22	0.0592 (9)	0.0615 (9)	0.0468 (8)	0.0004 (7)	0.0044 (7)	0.0006 (7)
C23	0.0766 (11)	0.0638 (11)	0.0662 (10)	0.0003 (8)	0.0051 (9)	0.0025 (8)
C24	0.0921 (14)	0.0663 (11)	0.0924 (14)	0.0089 (10)	0.0166 (11)	0.0132 (10)
C25	0.0896 (14)	0.0964 (16)	0.0806 (13)	0.0255 (12)	0.0008 (11)	0.0244 (12)
C26	0.1075 (17)	0.1034 (17)	0.0730 (13)	0.0144 (13)	−0.0259 (11)	0.0026 (12)
C31	0.0526 (9)	0.0480 (8)	0.0542 (9)	0.0032 (6)	0.0098 (7)	0.0021 (7)
C32	0.0468 (8)	0.0485 (8)	0.0499 (8)	0.0014 (6)	0.0111 (6)	0.0042 (6)
C33	0.0517 (9)	0.0554 (9)	0.0511 (8)	0.0011 (7)	0.0025 (7)	0.0063 (7)
C34	0.0495 (8)	0.0502 (8)	0.0482 (8)	0.0012 (6)	0.0112 (7)	0.0051 (6)
C35	0.0755 (11)	0.0532 (9)	0.0546 (9)	−0.0027 (8)	0.0021 (8)	0.0021 (7)
C36	0.0951 (13)	0.0473 (9)	0.0635 (10)	0.0031 (8)	0.0073 (9)	0.0056 (7)
C37	0.0675 (10)	0.0580 (9)	0.0541 (9)	0.0096 (8)	0.0097 (8)	0.0102 (7)
C38	0.0578 (9)	0.0624 (10)	0.0585 (9)	−0.0032 (8)	0.0006 (7)	0.0073 (7)
C39	0.0579 (9)	0.0493 (8)	0.0601 (9)	−0.0031 (7)	0.0059 (7)	0.0078 (7)

Geometric parameters (Å, º)

O1—C1	1.3688 (16)	C14—H14	0.9300
O1—C11	1.4023 (17)	C15—C16	1.371 (3)
O2—C2	1.3630 (16)	C15—H15	0.9300
O2—C21	1.4128 (17)	C16—H16	0.9300
N1—C12	1.3264 (19)	C21—C22	1.502 (2)
N1—C16	1.335 (2)	C21—H21A	0.9700
N2—C22	1.3271 (19)	C21—H21B	0.9700
N2—C26	1.345 (2)	C22—C23	1.370 (2)
N3—C33	1.1431 (18)	C23—C24	1.380 (2)
N4—C37	1.392 (2)	C23—H23	0.9300
N4—H4B	0.95 (2)	C24—C25	1.360 (3)
N4—H4A	0.89 (2)	C24—H24	0.9300
C1—C6	1.3718 (18)	C25—C26	1.352 (3)
C1—C2	1.4025 (19)	C25—H25	0.9300
C2—C3	1.374 (2)	C26—H26	0.9300
C3—C4	1.389 (2)	C31—C32	1.3473 (19)
C3—H3	0.9300	C31—H31	0.9300
C4—C5	1.3903 (19)	C32—C33	1.448 (2)
C4—H4	0.9300	C32—C34	1.4831 (18)
C5—C6	1.4060 (19)	C34—C39	1.3870 (19)
C5—C31	1.4564 (19)	C34—C35	1.396 (2)
C6—H6	0.9300	C35—C36	1.379 (2)
C11—C12	1.503 (2)	C35—H35	0.9300
C11—H11A	0.9700	C36—C37	1.393 (2)
C11—H11B	0.9700	C36—H36	0.9300
C12—C13	1.372 (2)	C37—C38	1.382 (2)
C13—C14	1.374 (3)	C38—C39	1.376 (2)
C13—H13	0.9300	C38—H38	0.9300
C14—C15	1.358 (3)	C39—H39	0.9300
C1—O1—C11	118.25 (11)	O2—C21—C22	107.48 (12)
C2—O2—C21	119.76 (11)	O2—C21—H21A	110.2
C12—N1—C16	116.36 (16)	C22—C21—H21A	110.2
C22—N2—C26	116.77 (17)	O2—C21—H21B	110.2
C37—N4—H4B	117.3 (13)	C22—C21—H21B	110.2
C37—N4—H4A	112.7 (15)	H21A—C21—H21B	108.5
H4B—N4—H4A	116.4 (19)	N2—C22—C23	122.97 (15)
O1—C1—C6	125.29 (12)	N2—C22—C21	113.95 (14)
O1—C1—C2	114.18 (12)	C23—C22—C21	123.08 (14)
C6—C1—C2	120.53 (13)	C22—C23—C24	118.67 (17)
O2—C2—C3	126.26 (13)	C22—C23—H23	120.7
O2—C2—C1	114.47 (12)	C24—C23—H23	120.7
C3—C2—C1	119.27 (13)	C25—C24—C23	119.00 (18)
C2—C3—C4	119.90 (13)	C25—C24—H24	120.5
C2—C3—H3	120.1	C23—C24—H24	120.5
C4—C3—H3	120.1	C26—C25—C24	118.67 (18)
C3—C4—C5	121.93 (14)	C26—C25—H25	120.7
C3—C4—H4	119.0	C24—C25—H25	120.7
C5—C4—H4	119.0	N2—C26—C25	123.89 (19)
C4—C5—C6	117.33 (13)	N2—C26—H26	118.1
C4—C5—C31	118.12 (13)	C25—C26—H26	118.1
C6—C5—C31	124.52 (13)	C32—C31—C5	132.90 (14)
C1—C6—C5	121.04 (13)	C32—C31—H31	113.6
C1—C6—H6	119.5	C5—C31—H31	113.6
C5—C6—H6	119.5	C31—C32—C33	121.16 (13)
O1—C11—C12	107.47 (12)	C31—C32—C34	124.73 (13)
O1—C11—H11A	110.2	C33—C32—C34	114.10 (12)
C12—C11—H11A	110.2	N3—C33—C32	177.17 (16)
O1—C11—H11B	110.2	C39—C34—C35	116.61 (13)
C12—C11—H11B	110.2	C39—C34—C32	121.59 (13)
H11A—C11—H11B	108.5	C35—C34—C32	121.80 (13)
N1—C12—C13	122.85 (15)	C36—C35—C34	121.17 (15)
N1—C12—C11	114.88 (14)	C36—C35—H35	119.4
C13—C12—C11	122.27 (15)	C34—C35—H35	119.4
C12—C13—C14	119.32 (18)	C35—C36—C37	121.43 (15)
C12—C13—H13	120.3	C35—C36—H36	119.3
C14—C13—H13	120.3	C37—C36—H36	119.3
C15—C14—C13	118.96 (19)	C38—C37—N4	121.36 (16)
C15—C14—H14	120.5	C38—C37—C36	117.52 (14)
C13—C14—H14	120.5	N4—C37—C36	121.09 (16)
C14—C15—C16	117.81 (19)	C39—C38—C37	120.87 (14)
C14—C15—H15	121.1	C39—C38—H38	119.6
C16—C15—H15	121.1	C37—C38—H38	119.6
N1—C16—C15	124.6 (2)	C38—C39—C34	122.39 (14)
N1—C16—H16	117.7	C38—C39—H39	118.8
C15—C16—H16	117.7	C34—C39—H39	118.8
C11—O1—C1—C6	−6.9 (2)	C26—N2—C22—C23	−1.0 (3)
C11—O1—C1—C2	173.89 (13)	C26—N2—C22—C21	178.49 (17)
C21—O2—C2—C3	3.6 (2)	O2—C21—C22—N2	171.32 (14)
C21—O2—C2—C1	−176.08 (13)	O2—C21—C22—C23	−9.2 (2)
O1—C1—C2—O2	−1.09 (18)	N2—C22—C23—C24	0.0 (3)
C6—C1—C2—O2	179.70 (12)	C21—C22—C23—C24	−179.40 (16)
O1—C1—C2—C3	179.23 (13)	C22—C23—C24—C25	1.4 (3)
C6—C1—C2—C3	0.0 (2)	C23—C24—C25—C26	−1.7 (3)
O2—C2—C3—C4	179.98 (14)	C22—N2—C26—C25	0.6 (3)
C1—C2—C3—C4	−0.4 (2)	C24—C25—C26—N2	0.8 (4)
C2—C3—C4—C5	0.3 (2)	C4—C5—C31—C32	175.56 (15)
C3—C4—C5—C6	0.1 (2)	C6—C5—C31—C32	−2.4 (3)
C3—C4—C5—C31	−177.94 (13)	C5—C31—C32—C33	3.3 (2)
O1—C1—C6—C5	−178.68 (13)	C5—C31—C32—C34	−175.23 (14)
C2—C1—C6—C5	0.4 (2)	C31—C32—C34—C39	−162.29 (14)
C4—C5—C6—C1	−0.5 (2)	C33—C32—C34—C39	19.11 (19)
C31—C5—C6—C1	177.43 (13)	C31—C32—C34—C35	18.4 (2)
C1—O1—C11—C12	175.28 (12)	C33—C32—C34—C35	−160.15 (14)
C16—N1—C12—C13	−1.1 (3)	C39—C34—C35—C36	0.9 (2)
C16—N1—C12—C11	178.01 (17)	C32—C34—C35—C36	−179.82 (14)
O1—C11—C12—N1	−144.35 (15)	C34—C35—C36—C37	−1.1 (3)
O1—C11—C12—C13	34.8 (2)	C35—C36—C37—C38	1.1 (2)
N1—C12—C13—C14	2.6 (3)	C35—C36—C37—N4	179.39 (16)
C11—C12—C13—C14	−176.45 (18)	N4—C37—C38—C39	−179.21 (15)
C12—C13—C14—C15	−1.2 (3)	C36—C37—C38—C39	−0.9 (2)
C13—C14—C15—C16	−1.4 (4)	C37—C38—C39—C34	0.8 (2)
C12—N1—C16—C15	−1.8 (3)	C35—C34—C39—C38	−0.7 (2)
C14—C15—C16—N1	3.1 (4)	C32—C34—C39—C38	179.97 (13)
C2—O2—C21—C22	174.24 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···N1^i	0.95 (2)	2.35 (2)	3.293 (3)	172.8 (18)
N4—H4A···N3^i	0.89 (2)	2.52 (2)	3.390 (3)	165.5 (19)
C6—H6···N3	0.93	2.59	3.431 (2)	151
C26—H26···N2^ii	0.93	2.65	3.339 (3)	131

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