2-(1-Naphthyl­imino)-1-acenaphthen-1-one

In the title compound, C₂₂H₁₃NO, the angle between the acenaphthenyl and naphthyl ring systems is 83.56 (3)°. In the crystal structure, the mol­ecules aggregate via π–π stacking and C—H...π(arene) inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.111
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C2     ...       1.53 Ang.

   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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: This work has involved two groups in two different Universities.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: COSMO/APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-(1-Naphthylimino)-1-acenaphthen-1-one

Crystal data

C22H13NO	F(000) = 640
Mr = 307.33	Dx = 1.356 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 87 reflections
a = 8.2350 (7) Å	θ = 2.1–57.9°
b = 15.4991 (13) Å	µ = 0.08 mm^−1
c = 11.9910 (12) Å	T = 295 K
β = 100.387 (3)°	Block, red
V = 1505.4 (2) Å^3	0.36 × 0.25 × 0.20 mm
Z = 4

Data collection

Bruker APEX-II CCD diffractometer	1698 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
Graphite monochromator	θmax = 25.5°, θmin = 3.6°
φ and ω scans	h = −9→9
12556 measured reflections	k = −18→18
2788 independent reflections	l = −14→14

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0317P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.045	(Δ/σ)max < 0.001
wR(F^2) = 0.111	Δρmax = 0.16 e Å^−3
S = 1.01	Δρmin = −0.15 e Å^−3
2788 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
218 parameters	Extinction coefficient: 0.0062 (16)
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
C1	0.1392 (2)	0.16516 (11)	0.38859 (14)	0.0449 (4)
C2	0.0206 (2)	0.10793 (12)	0.30684 (16)	0.0501 (5)
C3	0.0577 (2)	0.01825 (11)	0.34356 (15)	0.0460 (5)
C4	0.18218 (19)	0.02214 (10)	0.44095 (14)	0.0420 (4)
C5	0.23560 (19)	0.10705 (10)	0.47219 (15)	0.0428 (4)
C6	0.3545 (2)	0.11825 (11)	0.56627 (16)	0.0492 (5)
H1A	0.3931	0.1732	0.5884	0.059*
C7	0.4179 (2)	0.04512 (12)	0.62927 (16)	0.0534 (5)
H2	0.4969	0.0528	0.6944	0.064*
C8	0.3671 (2)	−0.03682 (11)	0.59794 (16)	0.0530 (5)
H3	0.4131	−0.0835	0.6411	0.064*
C9	0.2460 (2)	−0.05096 (11)	0.50101 (16)	0.0469 (5)
C10	0.1813 (2)	−0.13110 (11)	0.45640 (18)	0.0573 (5)
H6	0.2209	−0.182	0.4924	0.069*
C11	0.0616 (2)	−0.13464 (13)	0.36109 (18)	0.0611 (6)
H7	0.0218	−0.1882	0.3339	0.073*
C12	−0.0031 (2)	−0.06014 (13)	0.30325 (17)	0.0563 (5)
H8	−0.0852	−0.0639	0.2391	0.068*
C13	0.2552 (2)	0.29914 (11)	0.44608 (16)	0.0503 (5)
C14	0.2088 (3)	0.34240 (12)	0.53457 (18)	0.0615 (6)
H14	0.1022	0.3361	0.549	0.074*
C15	0.3221 (3)	0.39657 (13)	0.60401 (18)	0.0690 (6)
H15	0.2898	0.4255	0.6644	0.083*
C16	0.4773 (3)	0.40682 (12)	0.58361 (18)	0.0644 (6)
H16	0.5511	0.4422	0.6307	0.077*
C17	0.5283 (2)	0.36453 (11)	0.49197 (16)	0.0528 (5)
C18	0.4161 (2)	0.31019 (10)	0.42112 (15)	0.0470 (5)
C19	0.4697 (2)	0.26893 (11)	0.32848 (16)	0.0525 (5)
H19	0.3974	0.2331	0.2809	0.063*
C20	0.6249 (3)	0.28105 (13)	0.30846 (18)	0.0640 (6)
H22	0.658	0.2535	0.2474	0.077*
C21	0.7355 (3)	0.33445 (14)	0.37853 (19)	0.0679 (6)
H21	0.8415	0.3424	0.3637	0.081*
C22	0.6896 (2)	0.37469 (13)	0.46762 (19)	0.0634 (6)
H20	0.765	0.4097	0.5139	0.076*
N1	0.14006 (17)	0.24672 (10)	0.37324 (13)	0.0518 (4)
O1	−0.08050 (16)	0.13425 (9)	0.22765 (12)	0.0716 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0423 (10)	0.0469 (11)	0.0444 (11)	0.0015 (8)	0.0049 (9)	0.0049 (9)
C2	0.0429 (11)	0.0615 (12)	0.0443 (11)	−0.0015 (9)	0.0034 (9)	0.0038 (9)
C3	0.0421 (10)	0.0518 (11)	0.0446 (11)	−0.0032 (9)	0.0095 (9)	−0.0031 (9)
C4	0.0398 (10)	0.0439 (10)	0.0434 (11)	0.0017 (8)	0.0103 (8)	0.0009 (8)
C5	0.0406 (10)	0.0420 (10)	0.0447 (11)	0.0008 (8)	0.0044 (8)	0.0031 (8)
C6	0.0484 (10)	0.0462 (10)	0.0496 (11)	−0.0009 (9)	−0.0004 (9)	0.0008 (9)
C7	0.0526 (11)	0.0560 (12)	0.0471 (12)	0.0015 (9)	−0.0029 (9)	0.0060 (9)
C8	0.0563 (11)	0.0486 (11)	0.0530 (12)	0.0074 (9)	0.0065 (10)	0.0097 (9)
C9	0.0467 (10)	0.0457 (11)	0.0500 (11)	0.0010 (9)	0.0130 (9)	0.0016 (9)
C10	0.0697 (13)	0.0428 (11)	0.0622 (14)	−0.0012 (9)	0.0192 (11)	0.0015 (9)
C11	0.0716 (14)	0.0513 (12)	0.0636 (14)	−0.0143 (10)	0.0213 (12)	−0.0110 (10)
C12	0.0544 (11)	0.0643 (13)	0.0502 (12)	−0.0109 (10)	0.0095 (9)	−0.0098 (10)
C13	0.0565 (12)	0.0413 (10)	0.0505 (12)	0.0039 (9)	0.0023 (10)	0.0067 (9)
C14	0.0649 (13)	0.0573 (12)	0.0641 (14)	0.0024 (11)	0.0168 (11)	0.0048 (11)
C15	0.0966 (17)	0.0556 (12)	0.0578 (13)	0.0007 (12)	0.0220 (13)	−0.0049 (11)
C16	0.0812 (15)	0.0524 (12)	0.0579 (13)	−0.0127 (11)	0.0082 (12)	−0.0031 (10)
C17	0.0630 (13)	0.0428 (11)	0.0495 (12)	−0.0037 (9)	0.0017 (10)	0.0091 (9)
C18	0.0547 (12)	0.0390 (10)	0.0449 (11)	0.0047 (9)	0.0028 (9)	0.0092 (8)
C19	0.0606 (13)	0.0470 (11)	0.0475 (12)	0.0035 (9)	0.0035 (10)	0.0053 (9)
C20	0.0660 (14)	0.0687 (14)	0.0574 (14)	0.0126 (11)	0.0114 (12)	0.0100 (11)
C21	0.0586 (13)	0.0766 (15)	0.0676 (16)	0.0037 (12)	0.0091 (12)	0.0218 (13)
C22	0.0632 (14)	0.0625 (13)	0.0599 (14)	−0.0083 (10)	−0.0016 (11)	0.0129 (11)
N1	0.0494 (9)	0.0498 (10)	0.0531 (10)	0.0022 (7)	0.0009 (8)	0.0066 (8)
O1	0.0650 (9)	0.0784 (10)	0.0616 (10)	−0.0011 (7)	−0.0146 (8)	0.0085 (7)

Geometric parameters (Å, º)

C1—N1	1.278 (2)	C12—H8	0.93
C1—C5	1.470 (2)	C13—C14	1.367 (3)
C1—C2	1.535 (2)	C13—C18	1.420 (2)
C2—O1	1.215 (2)	C13—N1	1.423 (2)
C2—C3	1.473 (3)	C14—C15	1.410 (3)
C3—C12	1.369 (2)	C14—H14	0.93
C3—C4	1.409 (2)	C15—C16	1.353 (3)
C4—C9	1.394 (2)	C15—H15	0.93
C4—C5	1.416 (2)	C16—C17	1.407 (3)
C5—C6	1.365 (2)	C16—H16	0.93
C6—C7	1.409 (2)	C17—C18	1.415 (2)
C6—H1A	0.93	C17—C22	1.419 (3)
C7—C8	1.368 (2)	C18—C19	1.419 (2)
C7—H2	0.93	C19—C20	1.355 (3)
C8—C9	1.406 (3)	C19—H19	0.93
C8—H3	0.93	C20—C21	1.394 (3)
C9—C10	1.418 (2)	C20—H22	0.93
C10—C11	1.370 (3)	C21—C22	1.349 (3)
C10—H6	0.93	C21—H21	0.93
C11—C12	1.401 (3)	C22—H20	0.93
C11—H7	0.93
O1—C2—C1	124.92 (17)	C3—C12—C11	118.33 (18)
O1—C2—C3	128.78 (17)	C3—C12—H8	120.8
C1—C2—C3	106.29 (15)	C11—C12—H8	120.8
N1—C1—C2	119.95 (15)	C14—C13—C18	120.43 (17)
N1—C1—C5	133.49 (16)	C14—C13—N1	120.54 (17)
C1—N1—C13	119.81 (14)	C18—C13—N1	118.91 (16)
C5—C1—C2	106.54 (14)	C13—C14—C15	120.19 (19)
C12—C3—C4	119.72 (17)	C13—C14—H14	119.9
C12—C3—C2	133.54 (18)	C15—C14—H14	119.9
C4—C3—C2	106.74 (15)	C16—C15—C14	120.59 (19)
C9—C4—C3	122.92 (16)	C16—C15—H15	119.7
C9—C4—C5	123.27 (16)	C14—C15—H15	119.7
C3—C4—C5	113.81 (15)	C15—C16—C17	120.75 (19)
C6—C5—C4	118.63 (16)	C15—C16—H16	119.6
C6—C5—C1	134.80 (16)	C17—C16—H16	119.6
C4—C5—C1	106.57 (14)	C16—C17—C18	119.43 (18)
C5—C6—C7	118.80 (16)	C16—C17—C22	122.10 (19)
C5—C6—H1A	120.6	C18—C17—C22	118.46 (18)
C7—C6—H1A	120.6	C17—C18—C19	118.46 (17)
C8—C7—C6	122.29 (17)	C17—C18—C13	118.58 (17)
C8—C7—H2	118.9	C19—C18—C13	122.96 (17)
C6—C7—H2	118.9	C20—C19—C18	120.82 (18)
C7—C8—C9	120.52 (17)	C20—C19—H19	119.6
C7—C8—H3	119.7	C18—C19—H19	119.6
C9—C8—H3	119.7	C19—C20—C21	120.6 (2)
C4—C9—C8	116.47 (16)	C19—C20—H22	119.7
C4—C9—C10	115.88 (17)	C21—C20—H22	119.7
C8—C9—C10	127.65 (17)	C22—C21—C20	120.4 (2)
C11—C10—C9	121.00 (18)	C22—C21—H21	119.8
C11—C10—H6	119.5	C20—C21—H21	119.8
C9—C10—H6	119.5	C21—C22—C17	121.2 (2)
C10—C11—C12	122.14 (18)	C21—C22—H20	119.4
C10—C11—H7	118.9	C17—C22—H20	119.4
C12—C11—H7	118.9