Crystal structure and Hirshfeld surface analysis of 3,4-di­hydro-2H-anthra[1,2-b][1,4]dioxepine-8,13-dione

The dihedral angle between the mean plane of the anthra­quinone ring system and the dioxepine ring in the title compound is 16.29 (8)°. The packing is consolidated by C—H...O, π–π and C=O...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.055
• wR factor = 0.149
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.963 Why?
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.578 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        130 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist C4       -C13      .       1.45 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         80 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Info

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

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg et al., 2012); software used to prepare material for publication: PLATON (Spek, 2020) and publCIF (Westrip, 2010).

3,4-Dihydro-2H-anthra[1,2-b][1,4]dioxepine-8,13-dione

Crystal data

C17H12O4	F(000) = 584
Mr = 280.27	Dx = 1.439 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.2951 (2) Å	Cell parameters from 3436 reflections
b = 16.7714 (9) Å	θ = 2.4–29.7°
c = 18.0537 (11) Å	µ = 0.10 mm^−1
β = 95.941 (2)°	T = 173 K
V = 1293.51 (12) Å^3	Prism, colorless
Z = 4	0.12 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	2309 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.044
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 29.7°, θmin = 2.4°
Tmin = 0.988, Tmax = 0.990	h = −5→4
19692 measured reflections	k = −23→23
3436 independent reflections	l = −24→25

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0548P)^2 + 0.8849P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3436 reflections	Δρmax = 0.41 e Å^−3
190 parameters	Δρmin = −0.32 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	−0.2635 (5)	0.49906 (10)	0.64736 (8)	0.0546 (5)
O2	0.1717 (4)	0.34277 (9)	0.89646 (7)	0.0449 (4)
O3	0.0471 (3)	0.40325 (8)	0.56747 (6)	0.0293 (3)
O4	0.4204 (4)	0.25897 (8)	0.56830 (7)	0.0356 (3)
C1	0.3367 (5)	0.29496 (11)	0.63141 (10)	0.0274 (4)
C2	0.4523 (5)	0.26018 (11)	0.69817 (11)	0.0321 (4)
H2	0.590316	0.215932	0.697909	0.038*
C3	0.3704 (5)	0.28874 (11)	0.76486 (10)	0.0302 (4)
H3	0.451085	0.264092	0.810209	0.036*
C4	0.1701 (4)	0.35347 (10)	0.76600 (9)	0.0244 (4)
C5	0.0822 (5)	0.37964 (11)	0.83960 (10)	0.0285 (4)
C6	−0.1143 (5)	0.45162 (10)	0.84226 (9)	0.0269 (4)
C7	−0.1904 (5)	0.47948 (12)	0.91105 (10)	0.0351 (5)
H7	−0.121046	0.451264	0.955331	0.042*
C8	−0.3662 (6)	0.54788 (13)	0.91472 (11)	0.0407 (5)
H8	−0.413992	0.567394	0.961621	0.049*
C9	−0.4731 (5)	0.58819 (12)	0.85004 (11)	0.0377 (5)
H9	−0.595642	0.635045	0.852781	0.045*
C10	−0.4023 (5)	0.56056 (11)	0.78134 (11)	0.0308 (4)
H10	−0.478159	0.588130	0.737151	0.037*
C11	−0.2198 (4)	0.49227 (10)	0.77718 (9)	0.0248 (4)
C12	−0.1467 (5)	0.46397 (10)	0.70231 (9)	0.0271 (4)
C13	0.0595 (4)	0.39292 (10)	0.69919 (9)	0.0227 (4)
C14	0.1495 (4)	0.36425 (10)	0.63107 (9)	0.0238 (4)
C15	0.2543 (5)	0.40456 (12)	0.50847 (10)	0.0331 (4)
H15A	0.474823	0.405280	0.530766	0.040*
H15B	0.216063	0.453607	0.478396	0.040*
C16	0.1997 (6)	0.33217 (13)	0.45871 (11)	0.0389 (5)
H16A	0.001584	0.338786	0.426047	0.047*
H16B	0.372274	0.327239	0.426649	0.047*
C17	0.1829 (6)	0.25735 (13)	0.50493 (11)	0.0384 (5)
H17A	−0.026930	0.253140	0.522692	0.046*
H17B	0.214839	0.210027	0.473818	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0835 (14)	0.0550 (10)	0.0254 (7)	0.0370 (9)	0.0062 (8)	0.0053 (6)
O2	0.0590 (12)	0.0499 (9)	0.0257 (7)	0.0106 (8)	0.0036 (7)	0.0110 (6)
O3	0.0301 (8)	0.0378 (7)	0.0201 (6)	0.0062 (6)	0.0029 (5)	0.0009 (5)
O4	0.0345 (9)	0.0386 (8)	0.0346 (7)	0.0062 (6)	0.0078 (6)	−0.0075 (6)
C1	0.0248 (10)	0.0272 (9)	0.0307 (9)	−0.0022 (7)	0.0053 (7)	−0.0040 (7)
C2	0.0296 (11)	0.0267 (9)	0.0394 (10)	0.0036 (7)	0.0010 (8)	0.0015 (7)
C3	0.0297 (11)	0.0283 (9)	0.0313 (9)	0.0005 (7)	−0.0030 (8)	0.0054 (7)
C4	0.0245 (10)	0.0230 (8)	0.0252 (8)	−0.0033 (7)	0.0002 (7)	0.0022 (6)
C5	0.0314 (11)	0.0298 (9)	0.0237 (8)	−0.0042 (7)	0.0002 (7)	0.0022 (7)
C6	0.0309 (11)	0.0278 (8)	0.0220 (8)	−0.0070 (7)	0.0025 (7)	−0.0014 (6)
C7	0.0445 (14)	0.0376 (10)	0.0238 (9)	−0.0053 (9)	0.0064 (8)	−0.0010 (7)
C8	0.0538 (16)	0.0407 (11)	0.0295 (10)	−0.0035 (10)	0.0143 (9)	−0.0078 (8)
C9	0.0429 (14)	0.0317 (10)	0.0402 (11)	0.0007 (9)	0.0126 (9)	−0.0054 (8)
C10	0.0342 (12)	0.0264 (9)	0.0322 (9)	−0.0008 (7)	0.0054 (8)	−0.0002 (7)
C11	0.0274 (10)	0.0233 (8)	0.0239 (8)	−0.0051 (7)	0.0027 (7)	−0.0011 (6)
C12	0.0304 (11)	0.0274 (9)	0.0234 (8)	0.0015 (7)	0.0015 (7)	0.0006 (6)
C13	0.0233 (10)	0.0213 (8)	0.0231 (8)	−0.0039 (6)	0.0010 (6)	0.0006 (6)
C14	0.0218 (10)	0.0255 (8)	0.0236 (8)	−0.0033 (7)	0.0005 (7)	−0.0003 (6)
C15	0.0353 (12)	0.0407 (11)	0.0246 (9)	0.0002 (8)	0.0085 (8)	0.0014 (7)
C16	0.0396 (14)	0.0525 (12)	0.0256 (9)	0.0027 (10)	0.0080 (8)	−0.0079 (8)
C17	0.0376 (13)	0.0428 (11)	0.0357 (10)	−0.0027 (9)	0.0078 (9)	−0.0145 (8)

Geometric parameters (Å, º)

O1—C12	1.216 (2)	C7—H7	0.9500
O2—C5	1.226 (2)	C8—C9	1.386 (3)
O3—C14	1.355 (2)	C8—H8	0.9500
O3—C15	1.457 (2)	C9—C10	1.387 (3)
O4—C1	1.370 (2)	C9—H9	0.9500
O4—C17	1.452 (3)	C10—C11	1.394 (3)
C1—C2	1.384 (3)	C10—H10	0.9500
C1—C14	1.413 (3)	C11—C12	1.496 (2)
C2—C3	1.375 (3)	C12—C13	1.489 (2)
C2—H2	0.9500	C13—C14	1.411 (2)
C3—C4	1.387 (3)	C15—C16	1.514 (3)
C3—H3	0.9500	C15—H15A	0.9900
C4—C13	1.414 (2)	C15—H15B	0.9900
C4—C5	1.485 (2)	C16—C17	1.513 (3)
C5—C6	1.477 (3)	C16—H16A	0.9900
C6—C11	1.393 (2)	C16—H16B	0.9900
C6—C7	1.397 (2)	C17—H17A	0.9900
C7—C8	1.379 (3)	C17—H17B	0.9900
C14—O3—C15	117.23 (15)	C11—C10—H10	120.0
C1—O4—C17	116.12 (16)	C6—C11—C10	119.49 (16)
O4—C1—C2	115.92 (17)	C6—C11—C12	121.76 (16)
O4—C1—C14	123.85 (16)	C10—C11—C12	118.75 (15)
C2—C1—C14	120.22 (16)	O1—C12—C13	123.57 (16)
C3—C2—C1	120.95 (18)	O1—C12—C11	118.43 (17)
C3—C2—H2	119.5	C13—C12—C11	117.99 (14)
C1—C2—H2	119.5	C14—C13—C4	119.06 (16)
C2—C3—C4	120.08 (17)	C14—C13—C12	121.55 (15)
C2—C3—H3	120.0	C4—C13—C12	119.39 (15)
C4—C3—H3	120.0	O3—C14—C13	118.68 (15)
C3—C4—C13	120.52 (16)	O3—C14—C1	122.38 (15)
C3—C4—C5	117.40 (15)	C13—C14—C1	118.92 (15)
C13—C4—C5	122.07 (16)	O3—C15—C16	110.66 (16)
O2—C5—C6	121.06 (17)	O3—C15—H15A	109.5
O2—C5—C4	120.92 (18)	C16—C15—H15A	109.5
C6—C5—C4	118.02 (15)	O3—C15—H15B	109.5
C11—C6—C7	120.04 (18)	C16—C15—H15B	109.5
C11—C6—C5	120.65 (16)	H15A—C15—H15B	108.1
C7—C6—C5	119.31 (16)	C17—C16—C15	110.55 (16)
C8—C7—C6	120.04 (18)	C17—C16—H16A	109.5
C8—C7—H7	120.0	C15—C16—H16A	109.5
C6—C7—H7	120.0	C17—C16—H16B	109.5
C7—C8—C9	120.06 (18)	C15—C16—H16B	109.5
C7—C8—H8	120.0	H16A—C16—H16B	108.1
C9—C8—H8	120.0	O4—C17—C16	110.46 (18)
C8—C9—C10	120.42 (19)	O4—C17—H17A	109.6
C8—C9—H9	119.8	C16—C17—H17A	109.6
C10—C9—H9	119.8	O4—C17—H17B	109.6
C9—C10—C11	119.94 (18)	C16—C17—H17B	109.6
C9—C10—H10	120.0	H17A—C17—H17B	108.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O1^i	0.99	2.43	3.248 (2)	139
C15—H15A···O3^ii	0.99	2.48	3.461 (3)	171
C17—H17A···O4^iii	0.99	2.59	3.580 (3)	174

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