(2E,3E)-Ethyl 2-[(naphthalen-8-ylamino)methyl­ene]-3-(naphthalen-1-ylimino)butanoate

The title compound, C₂₇H₂₄N₂O₂, is built up from an unsaturated ester attached to two naphthylamine fragments. An intra­molecular N—H...N hydrogen bond may influence the conformation of the molecule.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.175
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Nonius, 1998); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(2E,3E)-Ethyl 2-[(naphthalen-8-ylamino)methylene]-3-(naphthalen-1-ylimino)butanoate

Crystal data

C27H24N2O2	F(000) = 864
Mr = 408.48	Dx = 1.258 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4953 reflections
a = 6.9502 (5) Å	θ = 1.0–27.5°
b = 16.2139 (7) Å	µ = 0.08 mm^−1
c = 19.2198 (7) Å	T = 173 K
β = 95.309 (2)°	Needle, yellow
V = 2156.6 (2) Å^3	0.3 × 0.2 × 0.15 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2750 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 27.4°, θmin = 2.5°
φ scans, and ω scans with κ offsets	h = −9→9
8395 measured reflections	k = −19→21
4889 independent reflections	l = −24→24

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.175	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0813P)^2 + 0.2247P] where P = (Fo^2 + 2Fc^2)/3
4889 reflections	(Δ/σ)max < 0.001
282 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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	0.4657 (3)	0.34180 (13)	0.83705 (10)	0.0935 (6)
O2	0.4544 (3)	0.47672 (12)	0.81203 (9)	0.0829 (5)
N1	0.7568 (2)	0.46638 (10)	0.64918 (8)	0.0490 (4)
H1	0.8273	0.4249	0.6398	0.059*
N2	0.8566 (3)	0.31610 (11)	0.68227 (8)	0.0573 (5)
C1	0.7530 (3)	0.53473 (12)	0.60347 (10)	0.0474 (5)
C2	0.7506 (3)	0.61360 (14)	0.62793 (13)	0.0640 (6)
H2	0.7532	0.6234	0.6757	0.077*
C3	0.7441 (4)	0.68048 (15)	0.58072 (17)	0.0798 (8)
H3	0.7398	0.7342	0.5975	0.096*
C4	0.7441 (3)	0.66698 (16)	0.51137 (16)	0.0763 (7)
H4	0.7399	0.7117	0.4810	0.092*
C5	0.7503 (3)	0.58639 (14)	0.48415 (12)	0.0602 (6)
C6	0.7526 (3)	0.5695 (2)	0.41154 (14)	0.0797 (8)
H6	0.7493	0.6132	0.3801	0.096*
C7	0.7593 (3)	0.4915 (2)	0.38728 (13)	0.0818 (8)
H7	0.7646	0.4822	0.3398	0.098*
C8	0.7583 (3)	0.42535 (18)	0.43272 (11)	0.0694 (7)
H8	0.7597	0.3718	0.4154	0.083*
C9	0.7553 (3)	0.43818 (13)	0.50238 (10)	0.0535 (5)
H9	0.7548	0.3930	0.5322	0.064*
C10	0.7528 (2)	0.51865 (12)	0.53068 (10)	0.0472 (5)
C11	0.9794 (3)	0.25179 (13)	0.66453 (10)	0.0553 (5)
C12	1.1575 (3)	0.23840 (15)	0.70003 (12)	0.0687 (6)
H12	1.1931	0.2673	0.7410	0.082*
C13	1.2864 (4)	0.18102 (17)	0.67468 (15)	0.0781 (7)
H13	1.4055	0.1718	0.6996	0.094*
C14	1.2395 (4)	0.13930 (15)	0.61479 (15)	0.0725 (7)
H14	1.3277	0.1023	0.5987	0.087*
C15	1.0593 (3)	0.15084 (13)	0.57618 (12)	0.0598 (6)
C16	1.0067 (4)	0.10987 (15)	0.51261 (13)	0.0744 (7)
H16	1.0935	0.0735	0.4950	0.089*
C17	0.8324 (5)	0.12239 (17)	0.47668 (14)	0.0841 (8)
H17	0.8008	0.0945	0.4349	0.101*
C18	0.6994 (4)	0.17699 (15)	0.50184 (13)	0.0740 (7)
H18	0.5797	0.1851	0.4769	0.089*
C19	0.7447 (3)	0.21819 (13)	0.56267 (11)	0.0580 (5)
H19	0.6550	0.2543	0.5790	0.070*
C20	0.9257 (3)	0.20730 (12)	0.60178 (11)	0.0520 (5)
C21	0.6602 (3)	0.46115 (13)	0.70539 (10)	0.0499 (5)
H21	0.5903	0.5074	0.7167	0.060*
C22	0.6541 (3)	0.39331 (13)	0.74862 (9)	0.0508 (5)
C23	0.7644 (3)	0.31861 (13)	0.73773 (10)	0.0525 (5)
C24	0.5191 (3)	0.39873 (16)	0.80273 (10)	0.0600 (6)
C25	0.7725 (4)	0.24872 (16)	0.78984 (12)	0.0782 (7)
H25A	0.8408	0.2030	0.7721	0.117*
H25B	0.6435	0.2319	0.7973	0.117*
H25C	0.8382	0.2668	0.8333	0.117*
C26	0.3021 (4)	0.4875 (2)	0.85772 (14)	0.0884 (9)
H26A	0.3154	0.4462	0.8944	0.106*
H26B	0.3144	0.5414	0.8796	0.106*
C27	0.1137 (4)	0.4802 (2)	0.81974 (17)	0.1121 (12)
H27A	0.1002	0.5212	0.7835	0.168*
H27B	0.0158	0.4884	0.8512	0.168*
H27C	0.0998	0.4263	0.7993	0.168*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0980 (14)	0.1113 (15)	0.0768 (11)	0.0005 (12)	0.0374 (10)	0.0293 (11)
O2	0.0802 (12)	0.0867 (13)	0.0888 (12)	−0.0070 (10)	0.0446 (10)	−0.0127 (10)
N1	0.0519 (9)	0.0509 (10)	0.0454 (9)	0.0073 (7)	0.0111 (7)	0.0054 (7)
N2	0.0714 (11)	0.0533 (10)	0.0481 (9)	0.0062 (9)	0.0098 (8)	0.0035 (8)
C1	0.0425 (10)	0.0468 (11)	0.0537 (11)	0.0037 (8)	0.0091 (8)	0.0058 (9)
C2	0.0620 (13)	0.0546 (13)	0.0767 (15)	0.0007 (10)	0.0145 (11)	−0.0061 (11)
C3	0.0735 (16)	0.0434 (13)	0.124 (2)	0.0027 (11)	0.0170 (16)	0.0062 (14)
C4	0.0632 (15)	0.0613 (15)	0.105 (2)	0.0014 (12)	0.0121 (14)	0.0347 (15)
C5	0.0387 (10)	0.0701 (15)	0.0720 (14)	0.0019 (10)	0.0065 (10)	0.0264 (12)
C6	0.0502 (13)	0.124 (2)	0.0654 (15)	0.0006 (15)	0.0068 (11)	0.0452 (17)
C7	0.0542 (14)	0.142 (3)	0.0493 (13)	0.0016 (16)	0.0057 (11)	0.0083 (16)
C8	0.0558 (13)	0.1003 (19)	0.0525 (12)	0.0001 (13)	0.0072 (10)	−0.0095 (13)
C9	0.0453 (11)	0.0653 (13)	0.0505 (11)	−0.0010 (10)	0.0066 (8)	0.0002 (10)
C10	0.0343 (9)	0.0570 (12)	0.0509 (11)	0.0016 (8)	0.0073 (8)	0.0095 (9)
C11	0.0648 (13)	0.0491 (12)	0.0525 (11)	0.0027 (10)	0.0083 (10)	0.0105 (9)
C12	0.0720 (15)	0.0663 (15)	0.0658 (13)	0.0010 (12)	−0.0038 (12)	0.0096 (12)
C13	0.0604 (14)	0.0810 (18)	0.0913 (19)	0.0088 (13)	−0.0012 (13)	0.0217 (15)
C14	0.0662 (15)	0.0634 (15)	0.0904 (18)	0.0151 (12)	0.0214 (13)	0.0153 (14)
C15	0.0647 (13)	0.0475 (12)	0.0690 (14)	0.0060 (10)	0.0160 (11)	0.0136 (10)
C16	0.0937 (18)	0.0582 (14)	0.0747 (16)	0.0144 (13)	0.0261 (14)	−0.0024 (12)
C17	0.108 (2)	0.0738 (17)	0.0689 (15)	0.0117 (16)	0.0011 (15)	−0.0112 (13)
C18	0.0808 (16)	0.0700 (15)	0.0688 (15)	0.0082 (13)	−0.0056 (13)	−0.0037 (13)
C19	0.0648 (13)	0.0498 (12)	0.0598 (12)	0.0070 (10)	0.0076 (10)	0.0045 (10)
C20	0.0585 (12)	0.0418 (10)	0.0568 (11)	0.0038 (9)	0.0124 (10)	0.0114 (9)
C21	0.0457 (10)	0.0609 (12)	0.0430 (10)	−0.0012 (9)	0.0040 (8)	−0.0044 (9)
C22	0.0484 (11)	0.0646 (13)	0.0394 (10)	−0.0049 (9)	0.0040 (8)	0.0016 (9)
C23	0.0553 (12)	0.0601 (13)	0.0415 (10)	−0.0068 (10)	0.0009 (9)	0.0047 (9)
C24	0.0545 (12)	0.0821 (16)	0.0435 (11)	−0.0107 (12)	0.0060 (9)	−0.0001 (11)
C25	0.0873 (17)	0.0787 (17)	0.0701 (15)	0.0024 (14)	0.0150 (13)	0.0273 (13)
C26	0.0744 (17)	0.121 (2)	0.0749 (17)	−0.0097 (16)	0.0357 (14)	−0.0243 (16)
C27	0.0734 (19)	0.164 (3)	0.102 (2)	−0.001 (2)	0.0246 (17)	−0.045 (2)

Geometric parameters (Å, º)

O1—C24	1.212 (3)	C12—H12	0.9300
O2—C24	1.359 (3)	C13—C14	1.349 (4)
O2—C26	1.447 (3)	C13—H13	0.9300
N1—C21	1.326 (2)	C14—C15	1.408 (3)
N1—C1	1.413 (2)	C14—H14	0.9300
N1—H1	0.8600	C15—C16	1.409 (3)
N2—C23	1.294 (3)	C15—C20	1.423 (3)
N2—C11	1.409 (3)	C16—C17	1.353 (4)
C1—C2	1.363 (3)	C16—H16	0.9300
C1—C10	1.423 (3)	C17—C18	1.398 (4)
C2—C3	1.412 (3)	C17—H17	0.9300
C2—H2	0.9300	C18—C19	1.358 (3)
C3—C4	1.351 (4)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.416 (3)
C4—C5	1.410 (3)	C19—H19	0.9300
C4—H4	0.9300	C21—C22	1.381 (3)
C5—C10	1.415 (3)	C21—H21	0.9300
C5—C6	1.424 (4)	C22—C23	1.459 (3)
C6—C7	1.350 (4)	C22—C24	1.466 (3)
C6—H6	0.9300	C23—C25	1.510 (3)
C7—C8	1.383 (4)	C25—H25A	0.9600
C7—H7	0.9300	C25—H25B	0.9600
C8—C9	1.357 (3)	C25—H25C	0.9600
C8—H8	0.9300	C26—C27	1.444 (4)
C9—C10	1.414 (3)	C26—H26A	0.9700
C9—H9	0.9300	C26—H26B	0.9700
C11—C12	1.374 (3)	C27—H27A	0.9600
C11—C20	1.425 (3)	C27—H27B	0.9600
C12—C13	1.409 (4)	C27—H27C	0.9600
C24—O2—C26	117.5 (2)	C14—C15—C20	118.7 (2)
C21—N1—C1	125.08 (17)	C16—C15—C20	118.5 (2)
C21—N1—H1	117.5	C17—C16—C15	121.3 (2)
C1—N1—H1	117.5	C17—C16—H16	119.3
C23—N2—C11	125.43 (18)	C15—C16—H16	119.3
C2—C1—N1	121.44 (19)	C16—C17—C18	120.5 (2)
C2—C1—C10	120.79 (19)	C16—C17—H17	119.7
N1—C1—C10	117.77 (17)	C18—C17—H17	119.7
C1—C2—C3	120.0 (2)	C19—C18—C17	120.1 (2)
C1—C2—H2	120.0	C19—C18—H18	120.0
C3—C2—H2	120.0	C17—C18—H18	120.0
C4—C3—C2	120.4 (2)	C18—C19—C20	121.3 (2)
C4—C3—H3	119.8	C18—C19—H19	119.3
C2—C3—H3	119.8	C20—C19—H19	119.3
C3—C4—C5	121.3 (2)	C19—C20—C15	118.21 (19)
C3—C4—H4	119.4	C19—C20—C11	122.44 (19)
C5—C4—H4	119.4	C15—C20—C11	119.35 (19)
C4—C5—C10	118.9 (2)	N1—C21—C22	125.94 (19)
C4—C5—C6	123.1 (2)	N1—C21—H21	117.0
C10—C5—C6	118.0 (2)	C22—C21—H21	117.0
C7—C6—C5	121.5 (2)	C21—C22—C23	121.93 (18)
C7—C6—H6	119.3	C21—C22—C24	115.9 (2)
C5—C6—H6	119.3	C23—C22—C24	122.06 (19)
C6—C7—C8	120.4 (2)	N2—C23—C22	116.82 (18)
C6—C7—H7	119.8	N2—C23—C25	122.1 (2)
C8—C7—H7	119.8	C22—C23—C25	121.05 (19)
C9—C8—C7	120.4 (3)	O1—C24—O2	121.0 (2)
C9—C8—H8	119.8	O1—C24—C22	126.0 (2)
C7—C8—H8	119.8	O2—C24—C22	113.0 (2)
C8—C9—C10	121.5 (2)	C23—C25—H25A	109.5
C8—C9—H9	119.2	C23—C25—H25B	109.5
C10—C9—H9	119.2	H25A—C25—H25B	109.5
C9—C10—C5	118.22 (19)	C23—C25—H25C	109.5
C9—C10—C1	123.23 (18)	H25A—C25—H25C	109.5
C5—C10—C1	118.55 (19)	H25B—C25—H25C	109.5
C12—C11—N2	122.3 (2)	C27—C26—O2	111.3 (2)
C12—C11—C20	119.6 (2)	C27—C26—H26A	109.4
N2—C11—C20	117.55 (18)	O2—C26—H26A	109.4
C11—C12—C13	120.3 (2)	C27—C26—H26B	109.4
C11—C12—H12	119.8	O2—C26—H26B	109.4
C13—C12—H12	119.8	H26A—C26—H26B	108.0
C14—C13—C12	121.0 (2)	C26—C27—H27A	109.5
C14—C13—H13	119.5	C26—C27—H27B	109.5
C12—C13—H13	119.5	H27A—C27—H27B	109.5
C13—C14—C15	121.0 (2)	C26—C27—H27C	109.5
C13—C14—H14	119.5	H27A—C27—H27C	109.5
C15—C14—H14	119.5	H27B—C27—H27C	109.5
C14—C15—C16	122.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2	0.86	1.95	2.596 (2)	131