5-Benzyl-8-(E)-benzyl­idene-6,7,7a,10a-tetra­hydro-5H-cis-cyclo­penta­[5,6]­pyrano­[3,3-c]­quinolin-6-one

In the title compound, C₂₉H₂₃NO₂, the quinolinone moiety is planar and the pyran ring is in a half-chair form. The cyclo­pentene fused with the pyran ring adopts an envelope conformation. There are C—H...O, C—H...π and π...π intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.132
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.90
PLAT480_ALERT_4_B Long H...A H-Bond Reported H19    ..  CG3     ..       3.29 Ang.

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.76 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for        C27
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C25
PLAT480_ALERT_4_C Long H...A H-Bond Reported H29    ..  O2      ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24B   ..  CG1     ..       3.03 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27    ..  CG2     ..       3.09 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C27    ..  CG2     ..       3.91 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C19    ..  CG3     ..       4.03 Ang.

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   9 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
   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
   7 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1998) and PLATON (Spek,1999); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

5-Benzyl-8-(E)-benzylidene-6,7,7a,10a-tetrahydro-5H-cis- cyclopenta[5,6]pyrano[3,3-c]quinolin-6-one

Crystal data

C29H23NO2	Z = 2
Mr = 417.48	F(000) = 440
Triclinic, P1	Dx = 1.280 Mg m^−3
a = 8.422 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.585 (3) Å	Cell parameters from 4237 reflections
c = 12.866 (3) Å	θ = 2.0–26.9°
α = 79.879 (4)°	µ = 0.08 mm^−1
β = 76.281 (4)°	T = 273 K
γ = 79.042 (4)°	Needle, yellow
V = 1083.6 (5) Å^3	0.32 × 0.20 × 0.12 mm

Data collection

Siemens SMART CCD area detector diffractometer	3097 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 26.9°, θmin = 2.0°
ω scans	h = −10→10
10877 measured reflections	k = −12→12
4237 independent reflections	l = −15→16

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0477P)^2 + 0.1865P] where P = (Fo^2 + 2Fc^2)/3
4237 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.14 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
N1	0.20520 (19)	0.32471 (14)	0.95421 (12)	0.0554 (4)
C9	0.1964 (2)	0.41559 (17)	1.02249 (15)	0.0518 (4)
C10	0.2808 (2)	0.52233 (17)	0.98468 (14)	0.0513 (4)
O1	0.44255 (18)	0.64358 (14)	0.84335 (11)	0.0750 (4)
C6	0.3687 (2)	0.53649 (18)	0.87361 (15)	0.0544 (5)
O2	0.30156 (19)	0.25164 (13)	0.79052 (11)	0.0744 (4)
C7	0.3755 (2)	0.44887 (18)	0.80770 (14)	0.0537 (5)
C2	0.1035 (2)	0.40318 (19)	1.12874 (16)	0.0622 (5)
H2	0.0465	0.3331	1.1548	0.075*
C8	0.2947 (2)	0.33574 (18)	0.84765 (15)	0.0563 (5)
C5	0.2729 (2)	0.61186 (19)	1.05447 (16)	0.0609 (5)
H5	0.3302	0.6820	1.0302	0.073*
C4	0.1819 (3)	0.5977 (2)	1.15801 (17)	0.0683 (6)
H4	0.1777	0.6578	1.2037	0.082*
C18	0.0615 (2)	0.70600 (18)	0.53506 (14)	0.0570 (5)
C17	0.2144 (3)	0.64059 (19)	0.56924 (14)	0.0611 (5)
H17	0.2482	0.5553	0.5551	0.073*
C16	0.3123 (2)	0.68508 (19)	0.61759 (15)	0.0593 (5)
C24	0.1094 (3)	0.2177 (2)	0.99109 (17)	0.0684 (6)
H24A	0.1087	0.1777	0.9290	0.082*
H24B	−0.0040	0.2533	1.0207	0.082*
C3	0.0965 (3)	0.4939 (2)	1.19429 (17)	0.0686 (6)
H3	0.0333	0.4853	1.2643	0.082*
C11	0.4694 (3)	0.4650 (2)	0.69327 (16)	0.0675 (6)
H11A	0.4190	0.4257	0.6491	0.081*
H11B	0.5823	0.4210	0.6894	0.081*
C13	0.5041 (3)	0.6874 (2)	0.72922 (17)	0.0705 (6)
H13	0.6224	0.6923	0.7154	0.085*
C19	−0.0462 (3)	0.8065 (2)	0.58338 (16)	0.0677 (6)
H19	−0.0223	0.8355	0.6413	0.081*
C22	−0.1248 (3)	0.7191 (2)	0.41517 (18)	0.0753 (6)
H22	−0.1512	0.6889	0.3587	0.090*
C23	0.0170 (3)	0.6628 (2)	0.45145 (16)	0.0665 (5)
H23	0.0848	0.5940	0.4192	0.080*
C25	0.1706 (3)	0.11366 (18)	1.07464 (16)	0.0626 (5)
C21	−0.2271 (3)	0.8202 (2)	0.46249 (19)	0.0776 (7)
H21	−0.3225	0.8591	0.4378	0.093*
C12	0.4700 (2)	0.6084 (2)	0.64994 (16)	0.0656 (5)
H12	0.5594	0.6138	0.5855	0.079*
C15	0.3000 (3)	0.8145 (2)	0.64520 (18)	0.0726 (6)
H15	0.2251	0.8856	0.6244	0.087*
C20	−0.1877 (3)	0.8636 (2)	0.5468 (2)	0.0778 (6)
H20	−0.2570	0.9318	0.5791	0.093*
C14	0.4083 (3)	0.8186 (2)	0.70346 (19)	0.0778 (6)
H14	0.4230	0.8938	0.7256	0.093*
C30	0.3324 (3)	0.0868 (2)	1.08468 (19)	0.0817 (7)
H30	0.4089	0.1363	1.0403	0.098*
C28	0.2730 (7)	−0.0854 (3)	1.2265 (3)	0.1338 (16)
H28	0.3076	−0.1532	1.2768	0.161*
C27	0.1119 (6)	−0.0581 (3)	1.2192 (3)	0.1415 (16)
H27	0.0355	−0.1058	1.2660	0.170*
C26	0.0600 (4)	0.0398 (2)	1.1427 (2)	0.0977 (8)
H26	−0.0504	0.0560	1.1371	0.117*
C29	0.3831 (4)	−0.0138 (2)	1.1607 (2)	0.1077 (10)
H29	0.4935	−0.0319	1.1662	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0598 (10)	0.0533 (9)	0.0556 (9)	−0.0106 (7)	−0.0229 (8)	0.0023 (7)
C9	0.0496 (10)	0.0534 (11)	0.0521 (11)	−0.0016 (9)	−0.0219 (9)	0.0016 (9)
C10	0.0493 (10)	0.0517 (11)	0.0535 (11)	−0.0026 (8)	−0.0219 (9)	0.0006 (9)
O1	0.0911 (11)	0.0740 (9)	0.0645 (9)	−0.0353 (8)	−0.0172 (8)	0.0035 (7)
C6	0.0505 (11)	0.0542 (11)	0.0588 (12)	−0.0085 (9)	−0.0217 (9)	0.0055 (9)
O2	0.1006 (11)	0.0639 (9)	0.0666 (9)	−0.0091 (8)	−0.0334 (8)	−0.0121 (7)
C7	0.0529 (11)	0.0554 (11)	0.0513 (11)	0.0007 (9)	−0.0200 (9)	−0.0007 (9)
C2	0.0604 (12)	0.0598 (12)	0.0614 (12)	−0.0043 (9)	−0.0158 (10)	0.0039 (10)
C8	0.0611 (12)	0.0543 (11)	0.0567 (12)	−0.0004 (9)	−0.0297 (10)	−0.0018 (9)
C5	0.0659 (13)	0.0552 (11)	0.0650 (13)	−0.0063 (9)	−0.0275 (10)	−0.0018 (10)
C4	0.0817 (15)	0.0660 (13)	0.0588 (13)	0.0004 (11)	−0.0246 (11)	−0.0125 (10)
C18	0.0689 (13)	0.0574 (11)	0.0434 (10)	−0.0191 (10)	−0.0114 (9)	0.0063 (9)
C17	0.0744 (13)	0.0592 (12)	0.0450 (10)	−0.0101 (10)	−0.0098 (10)	0.0013 (9)
C16	0.0631 (12)	0.0615 (12)	0.0469 (10)	−0.0134 (10)	−0.0078 (9)	0.0083 (9)
C24	0.0669 (13)	0.0703 (13)	0.0753 (14)	−0.0230 (11)	−0.0250 (11)	−0.0023 (11)
C3	0.0741 (14)	0.0683 (14)	0.0559 (12)	0.0033 (11)	−0.0129 (10)	−0.0049 (11)
C11	0.0649 (13)	0.0699 (13)	0.0588 (12)	0.0026 (10)	−0.0120 (10)	−0.0005 (10)
C13	0.0602 (12)	0.0804 (15)	0.0689 (14)	−0.0244 (11)	−0.0148 (10)	0.0118 (11)
C19	0.0703 (14)	0.0752 (14)	0.0592 (12)	−0.0142 (11)	−0.0154 (11)	−0.0076 (11)
C22	0.0930 (17)	0.0784 (15)	0.0623 (13)	−0.0336 (14)	−0.0293 (12)	0.0093 (12)
C23	0.0825 (15)	0.0643 (13)	0.0530 (12)	−0.0204 (11)	−0.0163 (11)	0.0033 (10)
C25	0.0788 (14)	0.0487 (11)	0.0617 (12)	−0.0173 (10)	−0.0115 (11)	−0.0080 (9)
C21	0.0706 (15)	0.0826 (16)	0.0797 (16)	−0.0249 (13)	−0.0288 (12)	0.0204 (13)
C12	0.0571 (12)	0.0761 (14)	0.0544 (12)	−0.0087 (10)	−0.0059 (9)	0.0055 (10)
C15	0.0758 (15)	0.0609 (13)	0.0830 (15)	−0.0177 (11)	−0.0265 (12)	0.0059 (11)
C20	0.0682 (14)	0.0760 (15)	0.0853 (16)	−0.0088 (12)	−0.0160 (13)	−0.0036 (12)
C14	0.0820 (16)	0.0676 (14)	0.0901 (16)	−0.0293 (12)	−0.0288 (13)	0.0058 (12)
C30	0.0990 (18)	0.0645 (14)	0.0885 (16)	−0.0211 (13)	−0.0420 (14)	0.0106 (12)
C28	0.266 (5)	0.0479 (16)	0.0765 (19)	0.000 (3)	−0.039 (3)	−0.0016 (14)
C27	0.215 (4)	0.0536 (18)	0.107 (2)	−0.022 (2)	0.048 (3)	0.0085 (16)
C26	0.105 (2)	0.0589 (14)	0.111 (2)	−0.0228 (13)	0.0191 (16)	−0.0093 (14)
C29	0.167 (3)	0.0622 (15)	0.110 (2)	−0.0027 (18)	−0.078 (2)	−0.0032 (16)

Geometric parameters (Å, º)

N1—C9	1.393 (2)	C11—C12	1.523 (3)
N1—C8	1.396 (2)	C11—H11A	0.9700
N1—C24	1.461 (2)	C11—H11B	0.9700
C9—C2	1.402 (3)	C13—C14	1.493 (3)
C9—C10	1.402 (2)	C13—C12	1.533 (3)
C10—C5	1.398 (3)	C13—H13	0.9800
C10—C6	1.442 (3)	C19—C20	1.378 (3)
O1—C6	1.350 (2)	C19—H19	0.9300
O1—C13	1.460 (2)	C22—C21	1.374 (3)
C6—C7	1.348 (3)	C22—C23	1.376 (3)
O2—C8	1.235 (2)	C22—H22	0.9300
C7—C8	1.445 (3)	C23—H23	0.9300
C7—C11	1.494 (3)	C25—C30	1.370 (3)
C2—C3	1.370 (3)	C25—C26	1.376 (3)
C2—H2	0.9300	C21—C20	1.379 (3)
C5—C4	1.369 (3)	C21—H21	0.9300
C5—H5	0.9300	C12—H12	0.9800
C4—C3	1.380 (3)	C15—C14	1.322 (3)
C4—H4	0.9300	C15—H15	0.9300
C18—C23	1.392 (3)	C20—H20	0.9300
C18—C19	1.393 (3)	C14—H14	0.9300
C18—C17	1.467 (3)	C30—C29	1.390 (3)
C17—C16	1.335 (3)	C30—H30	0.9300
C17—H17	0.9300	C28—C29	1.349 (5)
C16—C15	1.454 (3)	C28—C27	1.355 (5)
C16—C12	1.526 (3)	C28—H28	0.9300
C24—C25	1.505 (3)	C27—C26	1.381 (4)
C24—H24A	0.9700	C27—H27	0.9300
C24—H24B	0.9700	C26—H26	0.9300
C3—H3	0.9300	C29—H29	0.9300
C9—N1—C8	122.49 (16)	O1—C13—C14	106.89 (18)
C9—N1—C24	119.90 (17)	O1—C13—C12	115.44 (16)
C8—N1—C24	117.48 (16)	C14—C13—C12	103.15 (17)
N1—C9—C2	121.32 (17)	O1—C13—H13	110.3
N1—C9—C10	119.74 (17)	C14—C13—H13	110.3
C2—C9—C10	118.94 (18)	C12—C13—H13	110.3
C5—C10—C9	119.20 (18)	C20—C19—C18	121.1 (2)
C5—C10—C6	122.84 (17)	C20—C19—H19	119.5
C9—C10—C6	117.94 (17)	C18—C19—H19	119.5
C6—O1—C13	120.41 (16)	C21—C22—C23	119.9 (2)
C7—C6—O1	124.07 (18)	C21—C22—H22	120.1
C7—C6—C10	121.97 (17)	C23—C22—H22	120.1
O1—C6—C10	113.96 (17)	C22—C23—C18	121.8 (2)
C6—C7—C8	120.26 (17)	C22—C23—H23	119.1
C6—C7—C11	120.87 (18)	C18—C23—H23	119.1
C8—C7—C11	118.86 (18)	C30—C25—C26	118.3 (2)
C3—C2—C9	120.25 (19)	C30—C25—C24	123.09 (19)
C3—C2—H2	119.9	C26—C25—C24	118.6 (2)
C9—C2—H2	119.9	C22—C21—C20	119.7 (2)
O2—C8—N1	120.32 (18)	C22—C21—H21	120.2
O2—C8—C7	122.17 (19)	C20—C21—H21	120.2
N1—C8—C7	117.51 (17)	C11—C12—C16	117.12 (17)
C4—C5—C10	120.92 (19)	C11—C12—C13	113.70 (17)
C4—C5—H5	119.5	C16—C12—C13	103.85 (17)
C10—C5—H5	119.5	C11—C12—H12	107.2
C5—C4—C3	119.7 (2)	C16—C12—H12	107.2
C5—C4—H4	120.1	C13—C12—H12	107.2
C3—C4—H4	120.1	C14—C15—C16	111.6 (2)
C23—C18—C19	117.20 (19)	C14—C15—H15	124.2
C23—C18—C17	118.51 (19)	C16—C15—H15	124.2
C19—C18—C17	124.25 (18)	C19—C20—C21	120.3 (2)
C16—C17—C18	129.74 (19)	C19—C20—H20	119.8
C16—C17—H17	115.1	C21—C20—H20	119.8
C18—C17—H17	115.1	C15—C14—C13	111.6 (2)
C17—C16—C15	128.92 (19)	C15—C14—H14	124.2
C17—C16—C12	125.62 (19)	C13—C14—H14	124.2
C15—C16—C12	105.38 (17)	C25—C30—C29	120.6 (3)
N1—C24—C25	115.49 (16)	C25—C30—H30	119.7
N1—C24—H24A	108.4	C29—C30—H30	119.7
C25—C24—H24A	108.4	C29—C28—C27	119.7 (3)
N1—C24—H24B	108.4	C29—C28—H28	120.1
C25—C24—H24B	108.4	C27—C28—H28	120.1
H24A—C24—H24B	107.5	C28—C27—C26	120.7 (3)
C2—C3—C4	121.0 (2)	C28—C27—H27	119.7
C2—C3—H3	119.5	C26—C27—H27	119.7
C4—C3—H3	119.5	C25—C26—C27	120.4 (3)
C7—C11—C12	110.47 (17)	C25—C26—H26	119.8
C7—C11—H11A	109.6	C27—C26—H26	119.8
C12—C11—H11A	109.6	C28—C29—C30	120.3 (3)
C7—C11—H11B	109.6	C28—C29—H29	119.8
C12—C11—H11B	109.6	C30—C29—H29	119.8
H11A—C11—H11B	108.1
C8—N1—C9—C2	179.04 (15)	C5—C4—C3—C2	1.1 (3)
C24—N1—C9—C2	3.3 (2)	C6—C7—C11—C12	−29.8 (2)
C8—N1—C9—C10	−0.6 (2)	C8—C7—C11—C12	151.59 (17)
C24—N1—C9—C10	−176.29 (15)	C6—O1—C13—C14	117.20 (19)
N1—C9—C10—C5	−179.09 (15)	C6—O1—C13—C12	3.1 (3)
C2—C9—C10—C5	1.3 (2)	C23—C18—C19—C20	−2.4 (3)
N1—C9—C10—C6	2.6 (2)	C17—C18—C19—C20	179.88 (19)
C2—C9—C10—C6	−177.01 (15)	C21—C22—C23—C18	−0.5 (3)
C13—O1—C6—C7	14.2 (3)	C19—C18—C23—C22	2.0 (3)
C13—O1—C6—C10	−166.20 (16)	C17—C18—C23—C22	179.86 (18)
C5—C10—C6—C7	179.72 (16)	N1—C24—C25—C30	−26.4 (3)
C9—C10—C6—C7	−2.1 (2)	N1—C24—C25—C26	155.1 (2)
C5—C10—C6—O1	0.1 (2)	C23—C22—C21—C20	−0.6 (3)
C9—C10—C6—O1	178.32 (15)	C7—C11—C12—C16	−77.2 (2)
O1—C6—C7—C8	178.99 (16)	C7—C11—C12—C13	44.0 (2)
C10—C6—C7—C8	−0.6 (3)	C17—C16—C12—C11	−37.8 (3)
O1—C6—C7—C11	0.4 (3)	C15—C16—C12—C11	145.18 (18)
C10—C6—C7—C11	−179.16 (16)	C17—C16—C12—C13	−164.09 (18)
N1—C9—C2—C3	−179.91 (17)	C15—C16—C12—C13	18.92 (19)
C10—C9—C2—C3	−0.3 (3)	O1—C13—C12—C11	−32.5 (3)
C9—N1—C8—O2	178.71 (16)	C14—C13—C12—C11	−148.68 (17)
C24—N1—C8—O2	−5.5 (2)	O1—C13—C12—C16	95.91 (19)
C9—N1—C8—C7	−2.1 (2)	C14—C13—C12—C16	−20.3 (2)
C24—N1—C8—C7	173.75 (15)	C17—C16—C15—C14	172.9 (2)
C6—C7—C8—O2	−178.16 (17)	C12—C16—C15—C14	−10.3 (2)
C11—C7—C8—O2	0.4 (3)	C18—C19—C20—C21	1.4 (3)
C6—C7—C8—N1	2.6 (2)	C22—C21—C20—C19	0.2 (3)
C11—C7—C8—N1	−178.78 (15)	C16—C15—C14—C13	−3.5 (3)
C9—C10—C5—C4	−1.1 (3)	O1—C13—C14—C15	−106.7 (2)
C6—C10—C5—C4	177.08 (17)	C12—C13—C14—C15	15.4 (2)
C10—C5—C4—C3	−0.1 (3)	C26—C25—C30—C29	0.9 (3)
C23—C18—C17—C16	154.9 (2)	C24—C25—C30—C29	−177.5 (2)
C19—C18—C17—C16	−27.4 (3)	C29—C28—C27—C26	1.9 (5)
C18—C17—C16—C15	−3.7 (3)	C30—C25—C26—C27	0.3 (4)
C18—C17—C16—C12	−179.96 (17)	C24—C25—C26—C27	178.9 (2)
C9—N1—C24—C25	−72.0 (2)	C28—C27—C26—C25	−1.8 (5)
C8—N1—C24—C25	112.0 (2)	C27—C28—C29—C30	−0.7 (5)
C9—C2—C3—C4	−0.9 (3)	C25—C30—C29—C28	−0.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24A···O2	0.97	2.25	2.706 (2)	108
C22—H22···O2^i	0.93	2.47	3.275 (3)	145
C29—H29···O2^ii	0.93	2.68	3.388 (3)	134
C24—H24B···Cg1^iii	0.97	3.03	3.642	123
C27—H27···Cg2^iv	0.93	3.09	3.906	147
C19—H19···Cg3^iii	0.93	3.29	4.033	138

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