Diisopropyl anthracene-1,8-dicarboxyl­ate

In the title compound, C₂₂H₂₂O₄, the anthracene ring system is slightly non-planar. The two carboxyl­ate groups are both twisted away from the plane of the anthracene ring system by ca. 30°. The crystal packing is stabilized by C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.033
• wR factor = 0.101
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Diisopropyl anthracene-1,8-dicarboxylate

Crystal data

C22H22O4	F(000) = 744
Mr = 350.40	Dx = 1.283 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15531 reflections
a = 10.4097 (2) Å	θ = 3.1–27.5°
b = 7.9541 (1) Å	µ = 0.09 mm^−1
c = 22.2260 (4) Å	T = 153 K
β = 99.749 (1)°	Block, yellow
V = 1813.73 (5) Å^3	0.45 × 0.43 × 0.41 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3768 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.015
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
ω scans	h = −13→13
17341 measured reflections	k = −10→10
4161 independent reflections	l = −28→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.3998P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4161 reflections	Δρmax = 0.30 e Å^−3
240 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0079 (13)

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
O1	0.55172 (6)	0.60784 (8)	0.36918 (3)	0.02295 (16)
O2	0.46563 (7)	0.45601 (8)	0.28647 (3)	0.02518 (16)
O3	0.36508 (6)	0.61088 (8)	0.12099 (3)	0.02122 (16)
O4	0.24109 (7)	0.48628 (10)	0.04059 (3)	0.03037 (18)
C1	0.32721 (8)	0.63284 (11)	0.33564 (4)	0.01905 (19)
C2	0.31041 (9)	0.66863 (13)	0.39419 (4)	0.0245 (2)
H2	0.3782	0.6423	0.4271	0.029*
C3	0.19462 (10)	0.74375 (14)	0.40668 (4)	0.0288 (2)
H3	0.1848	0.7663	0.4476	0.035*
C4	0.09735 (10)	0.78364 (13)	0.35993 (4)	0.0266 (2)
H4	0.0204	0.8360	0.3685	0.032*
C5	−0.09063 (9)	0.78166 (13)	0.14214 (5)	0.0272 (2)
H5	−0.1665	0.8344	0.1517	0.033*
C6	−0.08609 (10)	0.73869 (14)	0.08340 (5)	0.0291 (2)
H6	−0.1594	0.7580	0.0524	0.035*
C7	0.02798 (9)	0.66526 (12)	0.06852 (4)	0.0246 (2)
H7	0.0299	0.6355	0.0273	0.030*
C8	0.13623 (9)	0.63562 (11)	0.11181 (4)	0.01951 (19)
C9	0.23551 (8)	0.63596 (11)	0.22368 (4)	0.01837 (18)
H9	0.3132	0.5865	0.2148	0.022*
C10	0.00889 (9)	0.78680 (12)	0.25015 (4)	0.0240 (2)
H10	−0.0672	0.8408	0.2590	0.029*
C11	0.10911 (9)	0.74798 (11)	0.29811 (4)	0.02126 (19)
C12	0.22528 (8)	0.66964 (11)	0.28477 (4)	0.01804 (18)
C13	0.13396 (8)	0.67352 (11)	0.17544 (4)	0.01814 (18)
C14	0.01687 (9)	0.74877 (11)	0.18961 (4)	0.02124 (19)
C15	0.45303 (9)	0.55510 (11)	0.32620 (4)	0.01916 (18)
C16	0.68102 (9)	0.53707 (12)	0.36724 (4)	0.0242 (2)
H16	0.6724	0.4172	0.3536	0.029*
C17	0.75291 (11)	0.54614 (14)	0.43216 (5)	0.0351 (3)
H17A	0.7571	0.6633	0.4460	0.042*
H17B	0.8415	0.5023	0.4340	0.042*
H17C	0.7068	0.4787	0.4586	0.042*
C18	0.74566 (10)	0.63823 (15)	0.32331 (5)	0.0346 (2)
H18A	0.6907	0.6372	0.2829	0.042*
H18B	0.8307	0.5889	0.3206	0.042*
H18C	0.7576	0.7543	0.3379	0.042*
C19	0.25147 (9)	0.56724 (11)	0.08750 (4)	0.02030 (19)
C20	0.48520 (9)	0.55572 (12)	0.10037 (4)	0.0222 (2)
H20	0.4738	0.4390	0.0836	0.027*
C21	0.58806 (10)	0.55694 (13)	0.15718 (5)	0.0275 (2)
H21A	0.5948	0.6701	0.1749	0.033*
H21B	0.6722	0.5244	0.1466	0.033*
H21C	0.5639	0.4771	0.1869	0.033*
C22	0.51495 (10)	0.67500 (14)	0.05145 (5)	0.0304 (2)
H22A	0.4417	0.6760	0.0174	0.036*
H22B	0.5940	0.6377	0.0369	0.036*
H22C	0.5284	0.7885	0.0685	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0192 (3)	0.0247 (3)	0.0236 (3)	0.0016 (2)	−0.0001 (2)	−0.0046 (3)
O2	0.0276 (3)	0.0256 (3)	0.0212 (3)	0.0049 (3)	0.0010 (3)	−0.0044 (3)
O3	0.0194 (3)	0.0259 (3)	0.0190 (3)	0.0006 (2)	0.0053 (2)	−0.0046 (2)
O4	0.0332 (4)	0.0355 (4)	0.0218 (3)	−0.0001 (3)	0.0029 (3)	−0.0093 (3)
C1	0.0200 (4)	0.0194 (4)	0.0179 (4)	−0.0022 (3)	0.0036 (3)	−0.0016 (3)
C2	0.0249 (5)	0.0301 (5)	0.0181 (4)	−0.0022 (4)	0.0029 (3)	−0.0027 (4)
C3	0.0293 (5)	0.0388 (5)	0.0200 (4)	−0.0028 (4)	0.0093 (4)	−0.0085 (4)
C4	0.0237 (5)	0.0316 (5)	0.0264 (5)	−0.0003 (4)	0.0097 (4)	−0.0078 (4)
C5	0.0191 (4)	0.0304 (5)	0.0311 (5)	0.0033 (4)	0.0016 (4)	0.0035 (4)
C6	0.0217 (5)	0.0364 (5)	0.0266 (5)	0.0005 (4)	−0.0037 (4)	0.0054 (4)
C7	0.0253 (5)	0.0281 (5)	0.0194 (4)	−0.0037 (4)	0.0006 (3)	0.0024 (4)
C8	0.0204 (4)	0.0192 (4)	0.0185 (4)	−0.0029 (3)	0.0022 (3)	0.0011 (3)
C9	0.0177 (4)	0.0193 (4)	0.0185 (4)	−0.0003 (3)	0.0042 (3)	−0.0002 (3)
C10	0.0197 (4)	0.0256 (5)	0.0279 (5)	0.0025 (3)	0.0072 (3)	−0.0015 (4)
C11	0.0203 (4)	0.0219 (4)	0.0227 (4)	−0.0020 (3)	0.0068 (3)	−0.0032 (3)
C12	0.0180 (4)	0.0180 (4)	0.0185 (4)	−0.0025 (3)	0.0039 (3)	−0.0008 (3)
C13	0.0185 (4)	0.0174 (4)	0.0186 (4)	−0.0022 (3)	0.0035 (3)	0.0007 (3)
C14	0.0185 (4)	0.0211 (4)	0.0239 (4)	−0.0003 (3)	0.0029 (3)	0.0015 (3)
C15	0.0215 (4)	0.0181 (4)	0.0172 (4)	−0.0007 (3)	0.0016 (3)	0.0023 (3)
C16	0.0196 (4)	0.0228 (4)	0.0285 (5)	0.0039 (3)	−0.0007 (4)	−0.0020 (4)
C17	0.0334 (5)	0.0342 (5)	0.0327 (5)	0.0050 (4)	−0.0086 (4)	0.0002 (4)
C18	0.0263 (5)	0.0409 (6)	0.0370 (6)	−0.0033 (4)	0.0063 (4)	−0.0001 (5)
C19	0.0245 (4)	0.0192 (4)	0.0171 (4)	−0.0012 (3)	0.0031 (3)	0.0015 (3)
C20	0.0224 (4)	0.0245 (4)	0.0213 (4)	0.0034 (3)	0.0083 (3)	−0.0035 (3)
C21	0.0242 (5)	0.0312 (5)	0.0267 (5)	0.0053 (4)	0.0037 (4)	−0.0036 (4)
C22	0.0325 (5)	0.0348 (5)	0.0266 (5)	0.0008 (4)	0.0126 (4)	0.0014 (4)

Geometric parameters (Å, º)

O1—C15	1.3459 (11)	C9—C12	1.4057 (12)
O1—C16	1.4663 (11)	C9—H9	0.9500
O2—C15	1.2072 (11)	C10—C11	1.3940 (13)
O3—C19	1.3323 (11)	C10—C14	1.3953 (13)
O3—C20	1.4697 (10)	C10—H10	0.9500
O4—C19	1.2146 (11)	C11—C12	1.4352 (12)
C1—C2	1.3719 (12)	C13—C14	1.4398 (12)
C1—C12	1.4434 (12)	C16—C18	1.5085 (15)
C1—C15	1.4949 (12)	C16—C17	1.5106 (14)
C2—C3	1.4143 (14)	C16—H16	1.0000
C2—H2	0.9500	C17—H17A	0.9800
C3—C4	1.3600 (14)	C17—H17B	0.9800
C3—H3	0.9500	C17—H17C	0.9800
C4—C11	1.4284 (12)	C18—H18A	0.9800
C4—H4	0.9500	C18—H18B	0.9800
C5—C6	1.3581 (14)	C18—H18C	0.9800
C5—C14	1.4262 (13)	C20—C21	1.5111 (13)
C5—H5	0.9500	C20—C22	1.5140 (13)
C6—C7	1.4119 (14)	C20—H20	1.0000
C6—H6	0.9500	C21—H21A	0.9800
C7—C8	1.3726 (12)	C21—H21B	0.9800
C7—H7	0.9500	C21—H21C	0.9800
C8—C13	1.4501 (12)	C22—H22A	0.9800
C8—C19	1.4988 (12)	C22—H22B	0.9800
C9—C13	1.4045 (12)	C22—H22C	0.9800
C15—O1—C16	116.97 (7)	C5—C14—C13	120.11 (8)
C19—O3—C20	118.01 (7)	O2—C15—O1	123.93 (8)
C2—C1—C12	120.39 (8)	O2—C15—C1	125.38 (8)
C2—C1—C15	118.32 (8)	O1—C15—C1	110.68 (7)
C12—C1—C15	121.29 (7)	O1—C16—C18	109.06 (8)
C1—C2—C3	121.58 (9)	O1—C16—C17	105.20 (8)
C1—C2—H2	119.2	C18—C16—C17	112.93 (9)
C3—C2—H2	119.2	O1—C16—H16	109.8
C4—C3—C2	119.84 (8)	C18—C16—H16	109.8
C4—C3—H3	120.1	C17—C16—H16	109.8
C2—C3—H3	120.1	C16—C17—H17A	109.5
C3—C4—C11	120.98 (9)	C16—C17—H17B	109.5
C3—C4—H4	119.5	H17A—C17—H17B	109.5
C11—C4—H4	119.5	C16—C17—H17C	109.5
C6—C5—C14	120.95 (9)	H17A—C17—H17C	109.5
C6—C5—H5	119.5	H17B—C17—H17C	109.5
C14—C5—H5	119.5	C16—C18—H18A	109.5
C5—C6—C7	119.79 (9)	C16—C18—H18B	109.5
C5—C6—H6	120.1	H18A—C18—H18B	109.5
C7—C6—H6	120.1	C16—C18—H18C	109.5
C8—C7—C6	122.01 (9)	H18A—C18—H18C	109.5
C8—C7—H7	119.0	H18B—C18—H18C	109.5
C6—C7—H7	119.0	O4—C19—O3	124.00 (9)
C7—C8—C13	120.06 (8)	O4—C19—C8	122.79 (8)
C7—C8—C19	114.95 (8)	O3—C19—C8	113.14 (7)
C13—C8—C19	124.98 (8)	O3—C20—C21	104.91 (7)
C13—C9—C12	121.77 (8)	O3—C20—C22	108.97 (7)
C13—C9—H9	119.1	C21—C20—C22	113.20 (8)
C12—C9—H9	119.1	O3—C20—H20	109.9
C11—C10—C14	122.03 (8)	C21—C20—H20	109.9
C11—C10—H10	119.0	C22—C20—H20	109.9
C14—C10—H10	119.0	C20—C21—H21A	109.5
C10—C11—C4	121.11 (8)	C20—C21—H21B	109.5
C10—C11—C12	119.07 (8)	H21A—C21—H21B	109.5
C4—C11—C12	119.82 (8)	C20—C21—H21C	109.5
C9—C12—C11	119.11 (8)	H21A—C21—H21C	109.5
C9—C12—C1	123.51 (8)	H21B—C21—H21C	109.5
C11—C12—C1	117.37 (8)	C20—C22—H22A	109.5
C9—C13—C14	118.50 (8)	C20—C22—H22B	109.5
C9—C13—C8	124.46 (8)	H22A—C22—H22B	109.5
C14—C13—C8	117.00 (8)	C20—C22—H22C	109.5
C10—C14—C5	120.41 (9)	H22A—C22—H22C	109.5
C10—C14—C13	119.47 (8)	H22B—C22—H22C	109.5
C12—C1—C2—C3	−0.73 (15)	C7—C8—C13—C14	−2.62 (13)
C15—C1—C2—C3	179.35 (9)	C19—C8—C13—C14	176.07 (8)
C1—C2—C3—C4	−0.67 (16)	C11—C10—C14—C5	176.39 (9)
C2—C3—C4—C11	1.18 (16)	C11—C10—C14—C13	−2.66 (14)
C14—C5—C6—C7	−2.04 (16)	C6—C5—C14—C10	−177.19 (9)
C5—C6—C7—C8	−0.18 (16)	C6—C5—C14—C13	1.85 (15)
C6—C7—C8—C13	2.55 (14)	C9—C13—C14—C10	1.92 (13)
C6—C7—C8—C19	−176.26 (9)	C8—C13—C14—C10	179.53 (8)
C14—C10—C11—C4	−178.17 (9)	C9—C13—C14—C5	−177.14 (8)
C14—C10—C11—C12	1.32 (14)	C8—C13—C14—C5	0.48 (13)
C3—C4—C11—C10	179.18 (9)	C16—O1—C15—O2	−0.94 (13)
C3—C4—C11—C12	−0.31 (15)	C16—O1—C15—C1	177.76 (7)
C13—C9—C12—C11	−1.43 (13)	C2—C1—C15—O2	146.97 (9)
C13—C9—C12—C1	179.93 (8)	C12—C1—C15—O2	−32.95 (13)
C10—C11—C12—C9	0.74 (13)	C2—C1—C15—O1	−31.70 (11)
C4—C11—C12—C9	−179.76 (8)	C12—C1—C15—O1	148.38 (8)
C10—C11—C12—C1	179.46 (8)	C15—O1—C16—C18	85.19 (9)
C4—C11—C12—C1	−1.04 (13)	C15—O1—C16—C17	−153.41 (8)
C2—C1—C12—C9	−179.79 (8)	C20—O3—C19—O4	−0.88 (13)
C15—C1—C12—C9	0.12 (13)	C20—O3—C19—C8	−177.98 (7)
C2—C1—C12—C11	1.54 (13)	C7—C8—C19—O4	−26.48 (13)
C15—C1—C12—C11	−178.54 (8)	C13—C8—C19—O4	154.78 (9)
C12—C9—C13—C14	0.10 (13)	C7—C8—C19—O3	150.66 (8)
C12—C9—C13—C8	−177.32 (8)	C13—C8—C19—O3	−28.08 (12)
C7—C8—C13—C9	174.84 (8)	C19—O3—C20—C21	−156.78 (8)
C19—C8—C13—C9	−6.48 (14)	C19—O3—C20—C22	81.71 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O3^i	1.00	2.55	3.440 (1)	149
C17—H17A···O4^ii	0.98	2.59	3.552 (1)	169
C21—H21A···O2^ii	0.98	2.55	3.492 (1)	162

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