2,3-Di­hydro-1H-cyclo­penta­[b]naphthalene-4,9-dione

The title compound, C₁₃H₁₀O₂, crystallizes with two almost planar mol­ecules in the asymmetric unit. In the crystal, slipped π–π stacking inter­actions help to establish the packing with the shortest centroid–centroid separation being 3.8195 (18) Å.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.060
• wR factor = 0.182
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.150
STRVA01_ALERT_2_C           Chirality of atom sites is inverted?
           From the CIF: _refine_ls_abs_structure_Flack    1.000
           From the CIF: _refine_ls_abs_structure_Flack_su    1.600
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.07 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00493 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C13 H10 O2
PLAT907_ALERT_2_C Flack x > 0.5, Structure Needs to be Inverted? .       1.00 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT013_ALERT_1_G No       _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT020_ALERT_3_G The Value of Rint is Greater Than 0.12 .........      0.150 Report
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      1.600 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.12 Report
PLAT073_ALERT_1_G H-atoms ref, but _hydrogen_treatment Reported as     constr Check
PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist C1       -C13      .       1.44 Ang.
PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist C14      -C26      .       1.45 Ang.
PLAT335_ALERT_2_G Check Large C6 Ring C-C Range C14      -C26            0.15 Ang.
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C13 H10 O2
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        69% Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       0.66 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: olex2.refine (Bourhis et al., 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2,3-Dihydro-1H-cyclopenta[b]naphthalene-4,9-dione

Crystal data

C13H10O2	Dx = 1.426 Mg m^−3
Mr = 198.22	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 16230 reflections
a = 7.4781 (1) Å	θ = 2.5–30.9°
c = 33.0219 (10) Å	µ = 0.10 mm^−1
V = 1846.65 (7) Å^3	T = 150 K
Z = 8	Block, colourless
F(000) = 832.447	0.21 × 0.13 × 0.04 mm

Data collection

Rigaku Oxford Diffraction CCD diffractometer	3230 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2851 reflections with I ≥ 2u(I)
Graphite monochromator	Rint = 0.150
ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	h = −10→10
Tmin = 0.636, Tmax = 1.000	k = −10→10
46308 measured reflections	l = −46→47

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.060	w = 1/[σ^2(Fo^2) + (0.1209P)^2 + 0.4577P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.182	(Δ/σ)max = 0.0002
S = 1.05	Δρmax = 0.35 e Å^−3
3230 reflections	Δρmin = −0.31 e Å^−3
271 parameters	Absolute structure: Flack (1983)
1 restraint	Absolute structure parameter: 1.0 (16)
34 constraints

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

	x	y	z	Uiso*/Ueq
O2	−0.1998 (3)	−1.0652 (3)	−0.53158 (8)	0.0313 (6)
O3	−0.4644 (3)	−0.5372 (3)	−0.46901 (7)	0.0314 (6)
O1	0.0178 (4)	−0.5172 (4)	−0.43869 (8)	0.0414 (7)
O4	−0.6811 (4)	−1.0853 (4)	−0.56192 (8)	0.0395 (7)
C13	−0.0343 (4)	−0.6351 (4)	−0.50334 (11)	0.0217 (8)
C8	−0.1458 (4)	−0.9450 (4)	−0.50952 (11)	0.0223 (8)
C15	−0.5855 (4)	−0.8269 (5)	−0.47358 (9)	0.0199 (7)
C7	−0.1437 (4)	−0.9603 (4)	−0.46489 (11)	0.0233 (8)
C2	−0.0910 (4)	−0.8149 (5)	−0.44071 (10)	0.0229 (8)
C1	−0.0324 (4)	−0.6440 (4)	−0.45901 (11)	0.0239 (8)
C16	−0.5999 (4)	−0.8685 (4)	−0.42918 (9)	0.0232 (7)
H16a	−0.4821 (4)	−0.8576 (4)	−0.41571 (9)	0.0278 (9)*
H16b	−0.6857 (4)	−0.7871 (4)	−0.41571 (9)	0.0278 (9)*
C6	−0.1933 (5)	−1.1217 (5)	−0.44638 (11)	0.0276 (8)
H6	−0.2294 (5)	−1.2205 (5)	−0.46249 (11)	0.0331 (10)*
C9	−0.0811 (4)	−0.7738 (4)	−0.52694 (9)	0.0202 (7)
C26	−0.5235 (4)	−0.6405 (4)	−0.53587 (11)	0.0218 (8)
C18	−0.6846 (5)	−1.1272 (5)	−0.47248 (10)	0.0272 (8)
H18a	−0.6030 (5)	−1.2287 (5)	−0.47791 (10)	0.0327 (10)*
H18b	−0.8087 (5)	−1.1644 (5)	−0.47857 (10)	0.0327 (10)*
C17	−0.6672 (5)	−1.0628 (4)	−0.42807 (10)	0.0257 (8)
H17a	−0.5815 (5)	−1.1392 (4)	−0.41314 (10)	0.0308 (9)*
H17b	−0.7846 (5)	−1.0690 (4)	−0.41429 (10)	0.0308 (9)*
C14	−0.5197 (4)	−0.6577 (4)	−0.49071 (10)	0.0219 (7)
C20	−0.6329 (4)	−0.9584 (4)	−0.54108 (11)	0.0260 (8)
C10	−0.0680 (4)	−0.7337 (4)	−0.57106 (10)	0.0240 (7)
H10a	0.0172 (4)	−0.8154 (4)	−0.58461 (10)	0.0288 (9)*
H10b	−0.1862 (4)	−0.7440 (4)	−0.58437 (10)	0.0288 (9)*
C21	−0.5758 (4)	−0.7871 (5)	−0.56003 (10)	0.0242 (8)
C25	−0.4721 (5)	−0.4794 (5)	−0.55371 (12)	0.0293 (8)
H25	−0.4349 (5)	−0.3815 (5)	−0.53744 (12)	0.0352 (10)*
C4	−0.1399 (4)	−0.9941 (6)	−0.38067 (12)	0.0334 (9)
H4	−0.1397 (4)	−1.0054 (6)	−0.35201 (12)	0.0401 (11)*
C24	−0.4762 (5)	−0.4644 (5)	−0.59580 (11)	0.0337 (9)
H24	−0.4440 (5)	−0.3544 (5)	−0.60823 (11)	0.0404 (11)*
C19	−0.6330 (4)	−0.9670 (4)	−0.49681 (11)	0.0197 (8)
C11	0.0008 (5)	−0.5378 (4)	−0.57204 (10)	0.0265 (8)
H11a	0.1181 (5)	−0.5317 (4)	−0.58585 (10)	0.0318 (9)*
H11b	−0.0847 (5)	−0.4605 (4)	−0.58681 (10)	0.0318 (9)*
C12	0.0185 (5)	−0.4755 (5)	−0.52765 (11)	0.0282 (8)
H12a	−0.0620 (5)	−0.3733 (5)	−0.52209 (11)	0.0339 (10)*
H12b	0.1430 (5)	−0.4396 (5)	−0.52153 (11)	0.0339 (10)*
C22	−0.5754 (5)	−0.7690 (5)	−0.60195 (10)	0.0306 (8)
H22	−0.6086 (5)	−0.8673 (5)	−0.61857 (10)	0.0368 (10)*
C23	−0.5266 (4)	−0.6074 (6)	−0.61955 (11)	0.0350 (9)
H23	−0.5279 (4)	−0.5954 (6)	−0.64819 (11)	0.0420 (11)*
C3	−0.0899 (4)	−0.8328 (5)	−0.39846 (10)	0.0292 (8)
H3	−0.0550 (4)	−0.7348 (5)	−0.38194 (10)	0.0351 (10)*
C5	−0.1894 (5)	−1.1370 (5)	−0.40428 (11)	0.0342 (9)
H5	−0.2213 (5)	−1.2470 (5)	−0.39185 (11)	0.0410 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0404 (14)	0.0252 (13)	0.0283 (13)	−0.0019 (11)	−0.0009 (11)	−0.0025 (10)
O3	0.0432 (15)	0.0280 (13)	0.0231 (13)	−0.0011 (11)	−0.0008 (11)	−0.0038 (11)
O1	0.0612 (18)	0.0350 (15)	0.0278 (15)	−0.0011 (12)	−0.0138 (13)	−0.0077 (13)
O4	0.0519 (17)	0.0388 (15)	0.0278 (14)	0.0009 (12)	−0.0114 (12)	−0.0089 (12)
C13	0.0200 (17)	0.0225 (19)	0.0226 (19)	0.0046 (13)	−0.0004 (12)	−0.0008 (12)
C8	0.0207 (16)	0.0237 (17)	0.0224 (18)	0.0048 (13)	0.0017 (13)	0.0018 (14)
C15	0.0193 (16)	0.0252 (17)	0.0152 (17)	0.0025 (13)	−0.0011 (13)	−0.0021 (13)
C7	0.0214 (18)	0.0285 (19)	0.0201 (18)	0.0087 (14)	0.0030 (12)	0.0069 (13)
C2	0.0180 (16)	0.0321 (19)	0.0186 (17)	0.0082 (13)	−0.0012 (13)	0.0000 (14)
C1	0.0257 (19)	0.0261 (19)	0.0198 (18)	0.0070 (14)	−0.0066 (12)	−0.0026 (13)
C16	0.0254 (17)	0.0268 (18)	0.0172 (17)	−0.0004 (13)	−0.0023 (14)	0.0036 (14)
C6	0.0210 (17)	0.032 (2)	0.0299 (19)	0.0049 (13)	0.0032 (14)	0.0059 (16)
C9	0.0165 (15)	0.0245 (17)	0.0198 (18)	0.0058 (12)	−0.0016 (12)	0.0016 (13)
C26	0.0207 (17)	0.0245 (18)	0.0202 (19)	0.0072 (13)	0.0032 (12)	−0.0001 (13)
C18	0.036 (2)	0.0204 (17)	0.0253 (19)	0.0014 (13)	0.0009 (15)	−0.0004 (14)
C17	0.0302 (18)	0.0264 (18)	0.0205 (17)	0.0016 (14)	0.0034 (14)	0.0011 (14)
C14	0.0215 (16)	0.0242 (17)	0.0200 (18)	0.0042 (13)	−0.0013 (12)	0.0002 (14)
C20	0.0250 (19)	0.031 (2)	0.022 (2)	0.0047 (14)	−0.0052 (13)	−0.0060 (14)
C10	0.0271 (18)	0.0243 (17)	0.0207 (17)	0.0020 (13)	0.0008 (14)	−0.0027 (14)
C21	0.0188 (17)	0.036 (2)	0.0173 (16)	0.0076 (14)	−0.0020 (13)	−0.0008 (14)
C25	0.0279 (19)	0.0276 (19)	0.032 (2)	0.0069 (14)	0.0060 (15)	0.0049 (16)
C4	0.0206 (18)	0.056 (2)	0.0234 (19)	0.0075 (15)	0.0009 (13)	0.0121 (17)
C24	0.0265 (19)	0.046 (2)	0.028 (2)	0.0086 (16)	0.0044 (15)	0.0196 (17)
C19	0.0178 (16)	0.0238 (19)	0.0176 (18)	0.0040 (13)	−0.0009 (12)	0.0010 (12)
C11	0.0280 (18)	0.0280 (18)	0.0235 (18)	0.0000 (13)	0.0009 (14)	0.0057 (15)
C12	0.0293 (18)	0.0250 (17)	0.030 (2)	−0.0005 (13)	0.0003 (15)	−0.0028 (15)
C22	0.0252 (18)	0.047 (2)	0.0198 (17)	0.0102 (15)	0.0000 (14)	−0.0021 (16)
C23	0.0242 (19)	0.064 (3)	0.0165 (18)	0.0111 (17)	0.0017 (13)	0.0057 (18)
C3	0.0209 (17)	0.044 (2)	0.0225 (18)	0.0096 (14)	−0.0060 (14)	−0.0002 (16)
C5	0.0239 (18)	0.046 (2)	0.033 (2)	0.0082 (15)	0.0094 (16)	0.0156 (18)

Geometric parameters (Å, º)

O2—C8	1.225 (4)	C18—C17	1.549 (5)
O3—C14	1.223 (4)	C18—C19	1.493 (5)
O1—C1	1.221 (4)	C17—H17a	0.9900
O4—C20	1.226 (4)	C17—H17b	0.9900
C13—C1	1.465 (5)	C20—C21	1.488 (5)
C13—C9	1.343 (5)	C20—C19	1.463 (5)
C13—C12	1.492 (5)	C10—H10a	0.9900
C8—C7	1.478 (5)	C10—H10b	0.9900
C8—C9	1.485 (5)	C10—C11	1.553 (5)
C15—C16	1.503 (4)	C21—C22	1.391 (5)
C15—C14	1.471 (5)	C25—H25	0.9500
C15—C19	1.346 (5)	C25—C24	1.395 (5)
C7—C2	1.406 (5)	C4—H4	0.9500
C7—C6	1.403 (5)	C4—C3	1.393 (5)
C2—C1	1.480 (5)	C4—C5	1.373 (6)
C2—C3	1.402 (5)	C24—H24	0.9500
C16—H16a	0.9900	C24—C23	1.379 (6)
C16—H16b	0.9900	C11—H11a	0.9900
C16—C17	1.538 (5)	C11—H11b	0.9900
C6—H6	0.9500	C11—C12	1.544 (5)
C6—C5	1.395 (5)	C12—H12a	0.9900
C9—C10	1.491 (4)	C12—H12b	0.9900
C26—C14	1.497 (5)	C22—H22	0.9500
C26—C21	1.411 (5)	C22—C23	1.390 (5)
C26—C25	1.395 (5)	C23—H23	0.9500
C18—H18a	0.9900	C3—H3	0.9500
C18—H18b	0.9900	C5—H5	0.9500
C9—C13—C1	123.2 (3)	C21—C20—O4	121.0 (3)
C12—C13—C1	124.8 (3)	C19—C20—O4	121.8 (3)
C12—C13—C9	112.0 (3)	C19—C20—C21	117.3 (3)
C7—C8—O2	122.6 (3)	H10a—C10—C9	111.08 (18)
C9—C8—O2	120.6 (3)	H10b—C10—C9	111.08 (17)
C9—C8—C7	116.7 (3)	H10b—C10—H10a	109.0
C14—C15—C16	125.2 (3)	C11—C10—C9	103.4 (3)
C19—C15—C16	112.1 (3)	C11—C10—H10a	111.08 (18)
C19—C15—C14	122.6 (3)	C11—C10—H10b	111.08 (19)
C2—C7—C8	120.6 (3)	C20—C21—C26	120.7 (3)
C6—C7—C8	119.9 (3)	C22—C21—C26	119.1 (3)
C6—C7—C2	119.5 (3)	C22—C21—C20	120.2 (3)
C1—C2—C7	121.3 (3)	H25—C25—C26	120.5 (2)
C3—C2—C7	119.5 (3)	C24—C25—C26	119.0 (4)
C3—C2—C1	119.2 (3)	C24—C25—H25	120.5 (2)
C13—C1—O1	121.1 (3)	C3—C4—H4	119.8 (2)
C2—C1—O1	122.5 (3)	C5—C4—H4	119.8 (2)
C2—C1—C13	116.3 (3)	C5—C4—C3	120.4 (4)
H16a—C16—C15	110.96 (17)	H24—C24—C25	119.7 (2)
H16b—C16—C15	110.96 (17)	C23—C24—C25	120.7 (4)
H16b—C16—H16a	109.0	C23—C24—H24	119.7 (2)
C17—C16—C15	104.0 (3)	C18—C19—C15	112.7 (3)
C17—C16—H16a	110.96 (18)	C20—C19—C15	122.3 (3)
C17—C16—H16b	110.96 (18)	C20—C19—C18	125.0 (3)
H6—C6—C7	120.0 (2)	H11a—C11—C10	110.31 (18)
C5—C6—C7	119.9 (4)	H11b—C11—C10	110.31 (19)
C5—C6—H6	120.0 (2)	H11b—C11—H11a	108.6
C8—C9—C13	121.7 (3)	C12—C11—C10	107.1 (3)
C10—C9—C13	113.3 (3)	C12—C11—H11a	110.31 (17)
C10—C9—C8	125.0 (3)	C12—C11—H11b	110.31 (18)
C21—C26—C14	120.1 (3)	C11—C12—C13	104.3 (3)
C25—C26—C14	119.3 (3)	H12a—C12—C13	110.90 (19)
C25—C26—C21	120.6 (3)	H12a—C12—C11	110.90 (18)
H18b—C18—H18a	109.0	H12b—C12—C13	110.90 (18)
C17—C18—H18a	111.00 (19)	H12b—C12—C11	110.90 (17)
C17—C18—H18b	111.00 (18)	H12b—C12—H12a	108.9
C19—C18—H18a	111.00 (18)	H22—C22—C21	120.0 (2)
C19—C18—H18b	111.00 (18)	C23—C22—C21	120.1 (4)
C19—C18—C17	103.8 (3)	C23—C22—H22	120.0 (2)
C18—C17—C16	107.4 (3)	C22—C23—C24	120.6 (4)
H17a—C17—C16	110.24 (18)	H23—C23—C24	119.7 (2)
H17a—C17—C18	110.24 (19)	H23—C23—C22	119.7 (2)
H17b—C17—C16	110.24 (19)	C4—C3—C2	120.1 (4)
H17b—C17—C18	110.24 (19)	H3—C3—C2	120.0 (2)
H17b—C17—H17a	108.5	H3—C3—C4	120.0 (2)
C15—C14—O3	121.4 (3)	C4—C5—C6	120.5 (4)
C26—C14—O3	121.8 (3)	H5—C5—C6	119.7 (2)
C26—C14—C15	116.8 (3)	H5—C5—C4	119.7 (2)
O2—C8—C7—C2	−176.0 (3)	C8—C7—C2—C3	−179.9 (3)
O2—C8—C7—C6	4.5 (4)	C8—C7—C6—C5	179.3 (3)
O2—C8—C9—C13	174.8 (3)	C8—C9—C10—C11	178.4 (3)
O2—C8—C9—C10	−2.6 (4)	C15—C16—C17—C18	1.4 (3)
O3—C14—C15—C16	2.7 (4)	C15—C14—C26—C21	−4.6 (3)
O3—C14—C15—C19	−174.3 (3)	C15—C14—C26—C25	176.5 (3)
O3—C14—C26—C21	175.3 (3)	C15—C19—C18—C17	1.7 (3)
O3—C14—C26—C25	−3.7 (4)	C15—C19—C20—C21	0.6 (3)
O1—C1—C13—C9	177.1 (3)	C7—C2—C3—C4	0.3 (3)
O1—C1—C13—C12	−1.4 (4)	C7—C6—C5—C4	1.0 (4)
O1—C1—C2—C7	−178.3 (3)	C2—C3—C4—C5	0.4 (4)
O1—C1—C2—C3	0.2 (4)	C16—C17—C18—C19	−1.8 (3)
O4—C20—C21—C26	178.9 (3)	C6—C5—C4—C3	−1.1 (4)
O4—C20—C21—C22	−0.4 (4)	C9—C10—C11—C12	−1.4 (3)
O4—C20—C19—C15	−178.0 (3)	C26—C21—C20—C19	0.3 (3)
O4—C20—C19—C18	1.9 (4)	C26—C21—C22—C23	−1.0 (3)
C13—C1—C2—C7	0.6 (3)	C26—C25—C24—C23	−1.4 (4)
C13—C1—C2—C3	179.1 (3)	C18—C19—C20—C21	−179.5 (3)
C13—C9—C8—C7	−4.4 (3)	C20—C21—C22—C23	178.3 (3)
C13—C9—C10—C11	0.8 (3)	C21—C22—C23—C24	0.7 (4)
C13—C12—C11—C10	1.5 (3)	C25—C24—C23—C22	0.5 (4)
C8—C7—C2—C1	−1.4 (3)