The crystal structure of the title compound, C
18H
12N
2O, is stabilized by intermolecular N—H
O hydrogen bonds and C—H
π interactions. N—H
O hydrogen bonds generate a
C(6) chain. The dihedral angle between the isoindoline group and the naphthalene ring system is 24.96 (12)°.
Supporting information
CCDC reference: 613665
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.032
- wR factor = 0.079
- Data-to-parameter ratio = 6.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.81
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 26.00
From the CIF: _reflns_number_total 1327
Count of symmetry unique reflns 1327
Completeness (_total/calc) 100.00%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
7,7a-dihydroisoindolo[2,1-
a]pyrimidin-12-one
top
Crystal data top
C18H12N2O | F(000) = 568 |
Mr = 272.30 | Dx = 1.391 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c-2ac | Cell parameters from 12797 reflections |
a = 19.8550 (13) Å | θ = 1.8–27.2° |
b = 4.7939 (3) Å | µ = 0.09 mm−1 |
c = 13.6612 (13) Å | T = 296 K |
V = 1300.31 (17) Å3 | Prismatic plate, light brown |
Z = 4 | 0.62 × 0.47 × 0.21 mm |
Data collection top
Stoe IPDS-2 diffractometer | 1327 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1146 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.050 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.1° |
ω scans | h = −24→24 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −5→5 |
Tmin = 0.945, Tmax = 0.981 | l = −16→16 |
12797 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.056P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.079 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.11 e Å−3 |
1327 reflections | Δρmin = −0.14 e Å−3 |
195 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.022 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1211 Friedel pairs |
Secondary atom site location: difference Fourier map | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.25741 (11) | 0.1729 (5) | 0.16001 (16) | 0.0592 (5) | |
C2 | 0.20675 (10) | 0.0002 (5) | 0.21149 (18) | 0.0576 (5) | |
C3 | 0.16087 (12) | −0.1870 (5) | 0.1734 (2) | 0.0696 (6) | |
H3 | 0.1587 | −0.2217 | 0.1065 | 0.084* | |
C4 | 0.11829 (12) | −0.3209 (6) | 0.2381 (2) | 0.0749 (7) | |
H4 | 0.0873 | −0.4499 | 0.2146 | 0.090* | |
C5 | 0.12113 (11) | −0.2657 (6) | 0.3374 (2) | 0.0714 (7) | |
H5 | 0.0917 | −0.3572 | 0.3795 | 0.086* | |
C6 | 0.16706 (10) | −0.0762 (5) | 0.37530 (19) | 0.0627 (5) | |
H6 | 0.1685 | −0.0379 | 0.4420 | 0.075* | |
C7 | 0.21054 (10) | 0.0537 (5) | 0.31079 (17) | 0.0546 (5) | |
C8 | 0.26388 (9) | 0.2682 (5) | 0.32911 (16) | 0.0528 (5) | |
H8 | 0.2435 | 0.4405 | 0.3539 | 0.063* | |
C9 | 0.37174 (9) | 0.3693 (4) | 0.39568 (15) | 0.0541 (5) | |
C10 | 0.41185 (11) | 0.3988 (6) | 0.47699 (18) | 0.0660 (6) | |
H10 | 0.4032 | 0.2940 | 0.5329 | 0.079* | |
C11 | 0.46593 (11) | 0.5871 (6) | 0.4757 (2) | 0.0753 (7) | |
H11 | 0.4921 | 0.6093 | 0.5316 | 0.090* | |
C12 | 0.48071 (12) | 0.7373 (6) | 0.3944 (2) | 0.0748 (7) | |
H12 | 0.5168 | 0.8609 | 0.3953 | 0.090* | |
C13 | 0.44206 (10) | 0.7085 (5) | 0.3085 (2) | 0.0640 (6) | |
C14 | 0.45728 (12) | 0.8515 (6) | 0.2210 (2) | 0.0774 (7) | |
H14 | 0.4933 | 0.9755 | 0.2195 | 0.093* | |
C15 | 0.41992 (14) | 0.8102 (6) | 0.1386 (2) | 0.0817 (8) | |
H15 | 0.4315 | 0.9032 | 0.0813 | 0.098* | |
C16 | 0.36414 (12) | 0.6289 (5) | 0.13881 (19) | 0.0713 (6) | |
H16 | 0.3389 | 0.6028 | 0.0822 | 0.086* | |
C17 | 0.34750 (10) | 0.4920 (5) | 0.22284 (17) | 0.0560 (5) | |
C18 | 0.38615 (10) | 0.5233 (5) | 0.30980 (16) | 0.0544 (5) | |
N1 | 0.29150 (8) | 0.3142 (4) | 0.23088 (13) | 0.0568 (4) | |
N2 | 0.31757 (9) | 0.1798 (4) | 0.39313 (14) | 0.0560 (4) | |
O1 | 0.26710 (9) | 0.1884 (4) | 0.07137 (12) | 0.0763 (5) | |
H2 | 0.3042 (13) | 0.131 (5) | 0.453 (2) | 0.073 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0657 (11) | 0.0664 (14) | 0.0456 (12) | 0.0046 (10) | −0.0029 (9) | −0.0009 (10) |
C2 | 0.0583 (10) | 0.0583 (12) | 0.0563 (13) | 0.0016 (9) | −0.0036 (9) | −0.0056 (10) |
C3 | 0.0703 (12) | 0.0699 (16) | 0.0688 (15) | −0.0002 (11) | −0.0107 (11) | −0.0100 (12) |
C4 | 0.0633 (12) | 0.0677 (15) | 0.094 (2) | −0.0060 (11) | −0.0096 (13) | −0.0079 (14) |
C5 | 0.0601 (12) | 0.0665 (14) | 0.0876 (18) | −0.0036 (11) | 0.0045 (12) | 0.0045 (13) |
C6 | 0.0582 (11) | 0.0654 (13) | 0.0646 (13) | 0.0001 (10) | 0.0050 (9) | 0.0008 (11) |
C7 | 0.0579 (11) | 0.0526 (11) | 0.0532 (12) | 0.0033 (8) | 0.0013 (9) | −0.0023 (10) |
C8 | 0.0540 (10) | 0.0574 (11) | 0.0471 (10) | 0.0030 (9) | 0.0021 (9) | −0.0033 (9) |
C9 | 0.0548 (10) | 0.0547 (12) | 0.0529 (11) | 0.0066 (9) | 0.0009 (9) | −0.0078 (10) |
C10 | 0.0654 (12) | 0.0744 (16) | 0.0584 (13) | 0.0058 (11) | −0.0057 (9) | −0.0066 (12) |
C11 | 0.0654 (13) | 0.0839 (18) | 0.0766 (17) | 0.0052 (13) | −0.0126 (11) | −0.0170 (15) |
C12 | 0.0587 (11) | 0.0729 (15) | 0.0926 (19) | −0.0039 (11) | −0.0041 (13) | −0.0187 (16) |
C13 | 0.0550 (11) | 0.0587 (14) | 0.0784 (16) | 0.0023 (9) | 0.0064 (11) | −0.0072 (12) |
C14 | 0.0692 (13) | 0.0701 (16) | 0.093 (2) | −0.0069 (12) | 0.0107 (14) | 0.0061 (15) |
C15 | 0.0836 (15) | 0.0837 (19) | 0.0777 (19) | −0.0093 (14) | 0.0135 (13) | 0.0162 (15) |
C16 | 0.0740 (13) | 0.0783 (16) | 0.0617 (15) | −0.0014 (12) | 0.0030 (11) | 0.0117 (13) |
C17 | 0.0560 (10) | 0.0579 (13) | 0.0543 (12) | 0.0034 (9) | 0.0035 (9) | 0.0025 (10) |
C18 | 0.0525 (10) | 0.0530 (12) | 0.0578 (12) | 0.0058 (8) | 0.0035 (9) | −0.0056 (10) |
N1 | 0.0609 (9) | 0.0631 (11) | 0.0463 (10) | −0.0038 (8) | −0.0002 (7) | 0.0016 (9) |
N2 | 0.0609 (9) | 0.0623 (11) | 0.0447 (10) | 0.0001 (7) | −0.0010 (8) | 0.0017 (9) |
O1 | 0.0860 (11) | 0.0974 (14) | 0.0454 (9) | −0.0036 (9) | −0.0047 (8) | −0.0007 (9) |
Geometric parameters (Å, º) top
C1—O1 | 1.228 (3) | C9—C18 | 1.415 (3) |
C1—N1 | 1.362 (3) | C10—C11 | 1.403 (4) |
C1—C2 | 1.480 (3) | C10—H10 | 0.9300 |
C2—C3 | 1.381 (3) | C11—C12 | 1.356 (4) |
C2—C7 | 1.383 (3) | C11—H11 | 0.9300 |
C3—C4 | 1.382 (4) | C12—C13 | 1.409 (4) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.383 (4) | C13—C14 | 1.411 (4) |
C4—H4 | 0.9300 | C13—C18 | 1.422 (3) |
C5—C6 | 1.387 (4) | C14—C15 | 1.362 (4) |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C6—C7 | 1.382 (3) | C15—C16 | 1.408 (4) |
C6—H6 | 0.9300 | C15—H15 | 0.9300 |
C7—C8 | 1.497 (3) | C16—C17 | 1.363 (3) |
C8—N2 | 1.443 (3) | C16—H16 | 0.9300 |
C8—N1 | 1.466 (3) | C17—N1 | 1.405 (3) |
C8—H8 | 0.9800 | C17—C18 | 1.422 (3) |
C9—C10 | 1.374 (3) | N2—H2 | 0.89 (3) |
C9—N2 | 1.408 (3) | | |
| | | |
O1—C1—N1 | 126.4 (2) | C11—C10—H10 | 120.0 |
O1—C1—C2 | 127.5 (2) | C12—C11—C10 | 121.2 (2) |
N1—C1—C2 | 106.14 (19) | C12—C11—H11 | 119.4 |
C3—C2—C7 | 121.8 (2) | C10—C11—H11 | 119.4 |
C3—C2—C1 | 129.2 (2) | C11—C12—C13 | 120.8 (2) |
C7—C2—C1 | 108.99 (19) | C11—C12—H12 | 119.6 |
C4—C3—C2 | 117.7 (2) | C13—C12—H12 | 119.6 |
C4—C3—H3 | 121.2 | C12—C13—C14 | 122.8 (2) |
C2—C3—H3 | 121.2 | C12—C13—C18 | 118.4 (3) |
C3—C4—C5 | 120.9 (2) | C14—C13—C18 | 118.8 (2) |
C3—C4—H4 | 119.5 | C15—C14—C13 | 120.9 (2) |
C5—C4—H4 | 119.5 | C15—C14—H14 | 119.6 |
C4—C5—C6 | 121.2 (3) | C13—C14—H14 | 119.6 |
C4—C5—H5 | 119.4 | C14—C15—C16 | 121.1 (3) |
C6—C5—H5 | 119.4 | C14—C15—H15 | 119.5 |
C7—C6—C5 | 117.9 (2) | C16—C15—H15 | 119.5 |
C7—C6—H6 | 121.1 | C17—C16—C15 | 119.3 (2) |
C5—C6—H6 | 121.1 | C17—C16—H16 | 120.3 |
C6—C7—C2 | 120.5 (2) | C15—C16—H16 | 120.3 |
C6—C7—C8 | 130.2 (2) | C16—C17—N1 | 123.3 (2) |
C2—C7—C8 | 109.26 (19) | C16—C17—C18 | 121.5 (2) |
N2—C8—N1 | 108.83 (15) | N1—C17—C18 | 115.19 (18) |
N2—C8—C7 | 114.97 (19) | C9—C18—C13 | 119.6 (2) |
N1—C8—C7 | 102.40 (17) | C9—C18—C17 | 121.90 (18) |
N2—C8—H8 | 110.1 | C13—C18—C17 | 118.5 (2) |
N1—C8—H8 | 110.1 | C1—N1—C17 | 129.75 (19) |
C7—C8—H8 | 110.1 | C1—N1—C8 | 112.96 (16) |
C10—C9—N2 | 121.9 (2) | C17—N1—C8 | 117.29 (17) |
C10—C9—C18 | 119.95 (19) | C9—N2—C8 | 112.93 (18) |
N2—C9—C18 | 118.06 (18) | C9—N2—H2 | 112.0 (17) |
C9—C10—C11 | 120.0 (2) | C8—N2—H2 | 114.5 (17) |
C9—C10—H10 | 120.0 | | |
| | | |
O1—C1—C2—C3 | 2.3 (4) | C15—C16—C17—C18 | −1.5 (4) |
N1—C1—C2—C3 | −177.9 (2) | C10—C9—C18—C13 | −0.2 (3) |
O1—C1—C2—C7 | −177.2 (2) | N2—C9—C18—C13 | −177.58 (18) |
N1—C1—C2—C7 | 2.5 (2) | C10—C9—C18—C17 | 177.71 (19) |
C7—C2—C3—C4 | 0.0 (3) | N2—C9—C18—C17 | 0.4 (3) |
C1—C2—C3—C4 | −179.4 (2) | C12—C13—C18—C9 | −1.4 (3) |
C2—C3—C4—C5 | 0.9 (4) | C14—C13—C18—C9 | 177.4 (2) |
C3—C4—C5—C6 | −0.5 (4) | C12—C13—C18—C17 | −179.4 (2) |
C4—C5—C6—C7 | −0.7 (4) | C14—C13—C18—C17 | −0.6 (3) |
C5—C6—C7—C2 | 1.6 (3) | C16—C17—C18—C9 | −176.1 (2) |
C5—C6—C7—C8 | 178.7 (2) | N1—C17—C18—C9 | 4.5 (3) |
C3—C2—C7—C6 | −1.3 (3) | C16—C17—C18—C13 | 1.8 (3) |
C1—C2—C7—C6 | 178.27 (19) | N1—C17—C18—C13 | −177.54 (19) |
C3—C2—C7—C8 | −178.98 (19) | O1—C1—N1—C17 | −4.9 (4) |
C1—C2—C7—C8 | 0.6 (2) | C2—C1—N1—C17 | 175.30 (19) |
C6—C7—C8—N2 | 61.6 (3) | O1—C1—N1—C8 | 175.0 (2) |
C2—C7—C8—N2 | −121.0 (2) | C2—C1—N1—C8 | −4.8 (2) |
C6—C7—C8—N1 | 179.4 (2) | C16—C17—N1—C1 | 23.2 (4) |
C2—C7—C8—N1 | −3.2 (2) | C18—C17—N1—C1 | −157.4 (2) |
N2—C9—C10—C11 | 179.0 (2) | C16—C17—N1—C8 | −156.7 (2) |
C18—C9—C10—C11 | 1.7 (3) | C18—C17—N1—C8 | 22.7 (3) |
C9—C10—C11—C12 | −1.7 (4) | N2—C8—N1—C1 | 127.15 (19) |
C10—C11—C12—C13 | 0.0 (4) | C7—C8—N1—C1 | 5.0 (2) |
C11—C12—C13—C14 | −177.2 (2) | N2—C8—N1—C17 | −52.9 (2) |
C11—C12—C13—C18 | 1.5 (4) | C7—C8—N1—C17 | −175.05 (17) |
C12—C13—C14—C15 | 177.7 (3) | C10—C9—N2—C8 | 150.8 (2) |
C18—C13—C14—C15 | −1.0 (4) | C18—C9—N2—C8 | −31.9 (2) |
C13—C14—C15—C16 | 1.5 (4) | N1—C8—N2—C9 | 56.1 (2) |
C14—C15—C16—C17 | −0.2 (4) | C7—C8—N2—C9 | 170.29 (17) |
C15—C16—C17—N1 | 177.9 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.89 (3) | 2.17 (3) | 2.959 (3) | 148 (2) |
C8—H8···Cg1ii | 0.98 | 2.80 | 3.568 | 136 |
Symmetry codes: (i) −x+1/2, y, z+1/2; (ii) x+1/2, −y+1, z. |