In the title compound, C
18H
11ClO
2, the pyranone ring adopts a boat conformation. There is one intramolecular C—H
O interaction, forming a six-membered ring. The crystal structure is stabilized by intermolecular C—H
O interactions and van der Waals forces.
Supporting information
CCDC reference: 226962
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.104
- Data-to-parameter ratio = 9.9
checkCIF/PLATON results
No syntax errors found
Alert level C
REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a
centrosymmetric structure
sine(theta)/lambda -0.1862
Proportion of unique data used 1.0000
Ratio reflections to parameters 9.8803
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.88
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C18 H11 Cl O2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
7-Chloromethylbenzo[
b]naphtho[1,2-
d]pyran-6-one
top
Crystal data top
C18H11ClO2 | F(000) = 608 |
Mr = 294.72 | Dx = 1.482 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9771 (5) Å | Cell parameters from 5237 reflections |
b = 16.1368 (8) Å | θ = 2.4–28.3° |
c = 8.2899 (4) Å | µ = 0.29 mm−1 |
β = 98.129 (1)° | T = 293 K |
V = 1321.25 (11) Å3 | Block, colourless |
Z = 4 | 0.50 × 0.44 × 0.42 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2312 independent reflections |
Radiation source: fine-focus sealed tube | 2111 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 2.4° |
ω scans | h = −11→11 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −19→16 |
Tmin = 0.869, Tmax = 0.888 | l = −9→9 |
6465 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0586P)2 + 0.4109P] where P = (Fo2 + 2Fc2)/3 |
2312 reflections | (Δ/σ)max < 0.001 |
234 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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 | |
Cl1 | 0.57400 (5) | 0.04931 (3) | 0.69791 (6) | 0.0606 (2) | |
O1 | 1.06207 (12) | −0.02294 (8) | 0.68746 (15) | 0.0491 (3) | |
O2 | 0.91060 (16) | 0.07091 (9) | 0.7126 (2) | 0.0739 (5) | |
C1 | 1.12861 (17) | −0.09531 (10) | 0.7363 (2) | 0.0415 (4) | |
C2 | 1.25689 (19) | −0.10377 (13) | 0.6925 (2) | 0.0521 (5) | |
C3 | 1.3334 (2) | −0.17165 (13) | 0.7473 (2) | 0.0547 (5) | |
C4 | 1.28303 (18) | −0.22966 (12) | 0.8453 (2) | 0.0502 (4) | |
C5 | 1.15440 (17) | −0.22109 (11) | 0.8863 (2) | 0.0426 (4) | |
C6 | 1.07073 (16) | −0.15433 (10) | 0.82790 (18) | 0.0361 (4) | |
C7 | 0.93398 (15) | −0.13882 (9) | 0.86682 (17) | 0.0336 (3) | |
C8 | 0.88200 (16) | −0.05866 (9) | 0.84402 (19) | 0.0363 (4) | |
C9 | 0.94942 (17) | 0.00196 (10) | 0.7489 (2) | 0.0446 (4) | |
C10 | 0.85193 (15) | −0.20265 (10) | 0.92574 (18) | 0.0346 (3) | |
C11 | 0.87364 (17) | −0.28889 (10) | 0.9083 (2) | 0.0401 (4) | |
C12 | 0.78871 (19) | −0.34572 (11) | 0.9626 (2) | 0.0464 (4) | |
C13 | 0.67945 (19) | −0.32074 (12) | 1.0397 (2) | 0.0496 (4) | |
C14 | 0.65283 (18) | −0.23876 (12) | 1.0537 (2) | 0.0464 (4) | |
C15 | 0.73459 (16) | −0.17806 (10) | 0.99271 (18) | 0.0381 (4) | |
C16 | 0.69621 (17) | −0.09338 (11) | 0.9865 (2) | 0.0427 (4) | |
C17 | 0.75984 (16) | −0.03556 (10) | 0.90550 (19) | 0.0387 (4) | |
C18 | 0.6941 (2) | 0.04808 (11) | 0.8831 (2) | 0.0474 (4) | |
H2 | 1.289 (2) | −0.0601 (13) | 0.627 (3) | 0.060 (6)* | |
H3 | 1.419 (3) | −0.1773 (14) | 0.716 (3) | 0.071 (7)* | |
H4 | 1.336 (2) | −0.2761 (14) | 0.887 (3) | 0.058 (6)* | |
H5 | 1.1245 (19) | −0.2597 (12) | 0.960 (2) | 0.047 (5)* | |
H11 | 0.943 (2) | −0.3080 (12) | 0.851 (2) | 0.048 (5)* | |
H12 | 0.802 (2) | −0.4021 (13) | 0.944 (2) | 0.054 (5)* | |
H13 | 0.624 (2) | −0.3615 (13) | 1.080 (2) | 0.057 (6)* | |
H14 | 0.577 (2) | −0.2189 (13) | 1.099 (3) | 0.057 (6)* | |
H16 | 0.622 (2) | −0.0759 (12) | 1.037 (2) | 0.053 (5)* | |
H18B | 0.758 (2) | 0.0941 (13) | 0.869 (2) | 0.055 (5)* | |
H18A | 0.633 (2) | 0.0568 (13) | 0.978 (3) | 0.068 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0518 (3) | 0.0569 (3) | 0.0683 (3) | 0.0071 (2) | −0.0085 (2) | 0.0093 (2) |
O1 | 0.0470 (7) | 0.0465 (7) | 0.0557 (7) | 0.0012 (5) | 0.0141 (6) | 0.0126 (5) |
O2 | 0.0686 (10) | 0.0438 (8) | 0.1143 (13) | 0.0092 (7) | 0.0298 (9) | 0.0281 (8) |
C1 | 0.0411 (9) | 0.0423 (9) | 0.0408 (8) | −0.0002 (7) | 0.0044 (7) | −0.0012 (7) |
C2 | 0.0485 (10) | 0.0598 (12) | 0.0513 (10) | −0.0041 (9) | 0.0182 (8) | −0.0012 (9) |
C3 | 0.0398 (10) | 0.0665 (12) | 0.0606 (11) | 0.0030 (9) | 0.0168 (9) | −0.0127 (9) |
C4 | 0.0412 (9) | 0.0491 (10) | 0.0595 (11) | 0.0080 (8) | 0.0047 (8) | −0.0088 (8) |
C5 | 0.0387 (9) | 0.0408 (9) | 0.0476 (10) | 0.0022 (7) | 0.0035 (7) | −0.0013 (7) |
C6 | 0.0351 (8) | 0.0370 (8) | 0.0357 (8) | −0.0013 (6) | 0.0031 (6) | −0.0035 (6) |
C7 | 0.0340 (8) | 0.0343 (8) | 0.0312 (7) | 0.0010 (6) | −0.0003 (6) | −0.0022 (6) |
C8 | 0.0358 (8) | 0.0349 (8) | 0.0364 (8) | 0.0005 (6) | −0.0008 (6) | −0.0022 (6) |
C9 | 0.0404 (9) | 0.0382 (9) | 0.0543 (10) | −0.0004 (7) | 0.0037 (7) | 0.0057 (7) |
C10 | 0.0332 (8) | 0.0369 (8) | 0.0324 (7) | 0.0009 (6) | −0.0001 (6) | 0.0008 (6) |
C11 | 0.0395 (9) | 0.0372 (9) | 0.0421 (9) | 0.0023 (7) | 0.0012 (7) | 0.0005 (7) |
C12 | 0.0499 (10) | 0.0378 (9) | 0.0488 (10) | −0.0031 (7) | −0.0018 (8) | 0.0029 (7) |
C13 | 0.0462 (10) | 0.0521 (10) | 0.0488 (10) | −0.0111 (8) | 0.0012 (8) | 0.0099 (8) |
C14 | 0.0383 (9) | 0.0570 (11) | 0.0444 (9) | −0.0009 (8) | 0.0069 (7) | 0.0058 (8) |
C15 | 0.0354 (8) | 0.0441 (9) | 0.0341 (8) | 0.0003 (6) | 0.0020 (6) | 0.0004 (6) |
C16 | 0.0361 (9) | 0.0509 (10) | 0.0418 (9) | 0.0070 (7) | 0.0078 (7) | −0.0039 (7) |
C17 | 0.0376 (9) | 0.0383 (8) | 0.0388 (8) | 0.0036 (6) | 0.0005 (6) | −0.0055 (6) |
C18 | 0.0481 (10) | 0.0406 (10) | 0.0524 (10) | 0.0083 (8) | 0.0028 (8) | −0.0069 (8) |
Geometric parameters (Å, º) top
Cl1—C18 | 1.8090 (19) | C8—C9 | 1.477 (2) |
O1—C9 | 1.358 (2) | C10—C15 | 1.421 (2) |
O1—C1 | 1.376 (2) | C10—C11 | 1.419 (2) |
O2—C9 | 1.202 (2) | C11—C12 | 1.368 (3) |
C1—C2 | 1.386 (2) | C11—H11 | 0.95 (2) |
C1—C6 | 1.393 (2) | C12—C13 | 1.398 (3) |
C2—C3 | 1.375 (3) | C12—H12 | 0.94 (2) |
C2—H2 | 0.97 (2) | C13—C14 | 1.358 (3) |
C3—C4 | 1.380 (3) | C13—H13 | 0.95 (2) |
C3—H3 | 0.93 (2) | C14—C15 | 1.413 (2) |
C4—C5 | 1.380 (2) | C14—H14 | 0.94 (2) |
C4—H4 | 0.95 (2) | C15—C16 | 1.418 (2) |
C5—C6 | 1.406 (2) | C16—C17 | 1.358 (2) |
C5—H5 | 0.95 (2) | C16—H16 | 0.95 (2) |
C6—C7 | 1.467 (2) | C17—C18 | 1.501 (2) |
C7—C8 | 1.397 (2) | C18—H18B | 1.00 (2) |
C7—C10 | 1.443 (2) | C18—H18A | 1.07 (2) |
C8—C17 | 1.435 (2) | | |
| | | |
C9—O1—C1 | 122.08 (13) | C15—C10—C7 | 118.09 (14) |
O1—C1—C2 | 115.57 (15) | C11—C10—C7 | 124.29 (15) |
O1—C1—C6 | 121.39 (15) | C12—C11—C10 | 120.89 (17) |
C2—C1—C6 | 123.02 (16) | C12—C11—H11 | 118.7 (12) |
C3—C2—C1 | 118.80 (18) | C10—C11—H11 | 120.3 (12) |
C3—C2—H2 | 123.7 (13) | C11—C12—C13 | 121.10 (17) |
C1—C2—H2 | 117.5 (13) | C11—C12—H12 | 119.0 (13) |
C2—C3—C4 | 120.26 (18) | C13—C12—H12 | 119.8 (13) |
C2—C3—H3 | 118.4 (14) | C14—C13—C12 | 119.65 (17) |
C4—C3—H3 | 121.4 (14) | C14—C13—H13 | 120.9 (13) |
C3—C4—C5 | 120.37 (18) | C12—C13—H13 | 119.5 (13) |
C3—C4—H4 | 121.1 (13) | C13—C14—C15 | 120.99 (17) |
C5—C4—H4 | 118.6 (13) | C13—C14—H14 | 122.7 (13) |
C4—C5—C6 | 121.29 (17) | C15—C14—H14 | 116.2 (13) |
C4—C5—H5 | 118.7 (12) | C14—C15—C16 | 120.95 (15) |
C6—C5—H5 | 119.9 (12) | C14—C15—C10 | 119.69 (15) |
C1—C6—C5 | 116.09 (15) | C16—C15—C10 | 119.20 (15) |
C1—C6—C7 | 118.25 (14) | C17—C16—C15 | 122.51 (16) |
C5—C6—C7 | 125.46 (15) | C17—C16—H16 | 117.7 (12) |
C8—C7—C10 | 119.30 (14) | C15—C16—H16 | 119.7 (12) |
C8—C7—C6 | 117.85 (14) | C16—C17—C8 | 118.48 (15) |
C10—C7—C6 | 122.84 (14) | C16—C17—C18 | 116.88 (15) |
C7—C8—C17 | 120.68 (15) | C8—C17—C18 | 124.62 (15) |
C7—C8—C9 | 119.82 (15) | C17—C18—Cl1 | 109.90 (12) |
C17—C8—C9 | 119.43 (14) | C17—C18—H18B | 114.0 (12) |
O2—C9—O1 | 115.74 (16) | Cl1—C18—H18B | 104.4 (12) |
O2—C9—C8 | 126.26 (17) | C17—C18—H18A | 108.1 (12) |
O1—C9—C8 | 117.89 (14) | Cl1—C18—H18A | 104.2 (12) |
C15—C10—C11 | 117.37 (15) | H18B—C18—H18A | 115.6 (17) |
| | | |
C9—O1—C1—C2 | −166.10 (16) | C17—C8—C9—O1 | −177.64 (14) |
C9—O1—C1—C6 | 12.1 (2) | C8—C7—C10—C15 | −13.9 (2) |
O1—C1—C2—C3 | 175.27 (16) | C6—C7—C10—C15 | 166.62 (13) |
C6—C1—C2—C3 | −2.9 (3) | C8—C7—C10—C11 | 160.23 (15) |
C1—C2—C3—C4 | −0.5 (3) | C6—C7—C10—C11 | −19.2 (2) |
C2—C3—C4—C5 | 1.4 (3) | C15—C10—C11—C12 | −3.6 (2) |
C3—C4—C5—C6 | 1.0 (3) | C7—C10—C11—C12 | −177.81 (15) |
O1—C1—C6—C5 | −172.96 (15) | C10—C11—C12—C13 | −1.2 (3) |
C2—C1—C6—C5 | 5.1 (2) | C11—C12—C13—C14 | 3.3 (3) |
O1—C1—C6—C7 | 2.1 (2) | C12—C13—C14—C15 | −0.5 (3) |
C2—C1—C6—C7 | −179.88 (15) | C13—C14—C15—C16 | 171.01 (16) |
C4—C5—C6—C1 | −4.1 (2) | C13—C14—C15—C10 | −4.4 (2) |
C4—C5—C6—C7 | −178.73 (16) | C11—C10—C15—C14 | 6.3 (2) |
C1—C6—C7—C8 | −14.7 (2) | C7—C10—C15—C14 | −179.11 (14) |
C5—C6—C7—C8 | 159.87 (15) | C11—C10—C15—C16 | −169.16 (14) |
C1—C6—C7—C10 | 164.83 (14) | C7—C10—C15—C16 | 5.4 (2) |
C5—C6—C7—C10 | −20.6 (2) | C14—C15—C16—C17 | −169.19 (16) |
C10—C7—C8—C17 | 11.4 (2) | C10—C15—C16—C17 | 6.3 (2) |
C6—C7—C8—C17 | −169.14 (13) | C15—C16—C17—C8 | −9.1 (2) |
C10—C7—C8—C9 | −165.66 (14) | C15—C16—C17—C18 | 169.35 (15) |
C6—C7—C8—C9 | 13.8 (2) | C7—C8—C17—C16 | 0.1 (2) |
C1—O1—C9—O2 | 170.87 (17) | C9—C8—C17—C16 | 177.12 (15) |
C1—O1—C9—C8 | −12.7 (2) | C7—C8—C17—C18 | −178.19 (15) |
C7—C8—C9—O2 | 175.38 (18) | C9—C8—C17—C18 | −1.2 (2) |
C17—C8—C9—O2 | −1.7 (3) | C16—C17—C18—Cl1 | −88.18 (17) |
C7—C8—C9—O1 | −0.6 (2) | C8—C17—C18—Cl1 | 90.13 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O2i | 0.95 (2) | 2.54 (2) | 3.371 (2) | 147 (2) |
C18—H18B···O2 | 1.00 (2) | 2.17 (2) | 2.768 (3) | 117 (2) |
Symmetry code: (i) −x+2, y−1/2, −z+3/2. |