7,16-Dioxatetra­cyclo[16.2^4,5.2^21,22.2^23,24.0^9,14]­tetracosa-1,3,5,9,11,13,17,19,21,23-decaene

In the title mol­ecule, C₂₂H₁₈O₂, the dihedral angles formed by the planes of the benzene rings are 70.0 (1), 82.9 (1) and 31.1 (1)°, respectively. In the crystal structure, inversion-related mol­ecules are linked by C—H...O hydrogen bonds to form dimeric pairs and these, translated along the a direction, are linked by weak C—H...O hydrogen bonds to form molecular chains. The crystal structure is further stabilized by weak C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.077
• wR factor = 0.196
• Data-to-parameter ratio = 12.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.119


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

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).

7,16-dioxatetracyclo(16.2^4,5.2^21,22.2^23,24.0^9,14)-tetracosa- 1,3,5,9,11,13,17,19,21,23-decaene

Crystal data

C22H18O2	F(000) = 664
Mr = 314.36	Dx = 1.302 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3501 reflections
a = 13.3086 (7) Å	θ = 3.5–28.4°
b = 5.8168 (3) Å	µ = 0.08 mm^−1
c = 20.8145 (11) Å	T = 183 K
β = 95.463 (1)°	Slab, colorless
V = 1604.00 (15) Å^3	0.36 × 0.22 × 0.16 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	1910 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.119
Graphite monochromator	θmax = 26.5°, θmin = 3.5°
Detector resolution: 8.33 pixels mm^-1	h = −15→16
ω scans	k = −7→7
8283 measured reflections	l = −23→26
3288 independent reflections

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)] = 0.077	Only H-atom coordinates refined
wR(F^2) = 0.196	w = 1/[σ^2(Fo^2) + (0.071P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3288 reflections	Δρmax = 0.33 e Å^−3
272 parameters	Δρmin = −0.33 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.061 (7)

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	0.44819 (17)	0.6278 (4)	0.07423 (11)	0.0266 (6)
O2	0.05225 (17)	0.6426 (4)	0.06238 (11)	0.0271 (6)
C1	0.3706 (3)	0.5309 (6)	0.02856 (17)	0.0235 (8)
H1A	0.333 (3)	0.417 (6)	0.0523 (17)	0.028*
H1B	0.411 (3)	0.457 (6)	−0.0062 (17)	0.028*
C2	0.3014 (3)	0.7142 (6)	−0.00255 (15)	0.0210 (8)
C3	0.3468 (3)	0.8864 (7)	−0.03696 (17)	0.0306 (9)
H3	0.417 (3)	0.885 (6)	−0.0379 (17)	0.037*
C4	0.2910 (3)	1.0539 (7)	−0.07133 (18)	0.0359 (10)
H4	0.329 (3)	1.176 (6)	−0.0994 (18)	0.043*
C5	0.1857 (3)	1.0530 (7)	−0.07216 (18)	0.0341 (10)
H5	0.140 (3)	1.182 (7)	−0.0942 (18)	0.041*
C6	0.1394 (3)	0.8845 (6)	−0.03737 (17)	0.0293 (9)
H6	0.069 (3)	0.903 (6)	−0.0376 (17)	0.035*
C7	0.1947 (3)	0.7169 (6)	−0.00186 (15)	0.0218 (8)
C8	0.1374 (3)	0.5428 (6)	0.03407 (18)	0.0249 (8)
H8A	0.104 (3)	0.422 (6)	0.0036 (17)	0.030*
H8B	0.178 (3)	0.469 (6)	0.0708 (17)	0.030*
C9	0.0785 (3)	0.7317 (6)	0.12410 (15)	0.0213 (8)
C10	0.0577 (3)	0.6010 (6)	0.17722 (17)	0.0233 (8)
H10	0.018 (3)	0.451 (6)	0.1703 (16)	0.028*
C11	0.0917 (3)	0.6759 (6)	0.23900 (17)	0.0256 (9)
H11	0.083 (3)	0.571 (6)	0.2750 (17)	0.031*
C12	0.1481 (3)	0.8759 (6)	0.24788 (16)	0.0228 (8)
C13	0.1593 (3)	1.0152 (6)	0.19415 (17)	0.0246 (8)
H13	0.204 (3)	1.168 (6)	0.2002 (16)	0.030*
C14	0.1247 (3)	0.9449 (6)	0.13233 (17)	0.0245 (8)
H14	0.139 (3)	1.034 (6)	0.0921 (17)	0.029*
C15	0.2118 (3)	0.9287 (6)	0.30965 (17)	0.0274 (9)
H15	0.184 (3)	0.978 (6)	0.3495 (18)	0.033*
C16	0.3114 (3)	0.9090 (6)	0.31151 (17)	0.0242 (8)
H16	0.355 (3)	0.962 (6)	0.3524 (17)	0.029*
C17	0.3599 (3)	0.8278 (5)	0.25381 (15)	0.0192 (8)
C18	0.4207 (3)	0.9665 (6)	0.21956 (16)	0.0202 (8)
H18	0.441 (3)	1.122 (6)	0.2371 (16)	0.024*
C19	0.4489 (3)	0.8991 (6)	0.15960 (16)	0.0214 (8)
H19	0.486 (3)	0.991 (6)	0.1353 (16)	0.026*
C20	0.4174 (2)	0.6889 (6)	0.13388 (15)	0.0188 (7)
C21	0.3640 (3)	0.5395 (6)	0.16992 (16)	0.0211 (8)
H21	0.345 (3)	0.392 (6)	0.1529 (16)	0.025*
C22	0.3350 (3)	0.6094 (6)	0.22915 (15)	0.0198 (8)
H22	0.287 (3)	0.502 (6)	0.2543 (15)	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0172 (13)	0.0413 (15)	0.0221 (13)	−0.0017 (12)	0.0059 (10)	−0.0079 (11)
O2	0.0188 (13)	0.0378 (15)	0.0244 (13)	−0.0001 (12)	0.0004 (10)	−0.0057 (11)
C1	0.0192 (19)	0.030 (2)	0.0218 (19)	−0.0029 (17)	0.0033 (15)	−0.0067 (16)
C2	0.0214 (19)	0.0263 (19)	0.0149 (17)	−0.0012 (16)	0.0004 (14)	−0.0064 (14)
C3	0.033 (2)	0.037 (2)	0.0233 (19)	−0.004 (2)	0.0092 (17)	−0.0055 (17)
C4	0.056 (3)	0.028 (2)	0.025 (2)	−0.004 (2)	0.0063 (19)	0.0002 (17)
C5	0.048 (3)	0.030 (2)	0.024 (2)	0.009 (2)	0.0049 (18)	0.0012 (17)
C6	0.032 (2)	0.033 (2)	0.024 (2)	0.0095 (19)	0.0060 (17)	−0.0004 (16)
C7	0.027 (2)	0.0226 (19)	0.0160 (17)	0.0011 (16)	0.0028 (14)	−0.0057 (14)
C8	0.0213 (19)	0.026 (2)	0.028 (2)	−0.0004 (17)	0.0042 (16)	−0.0039 (16)
C9	0.0188 (18)	0.0254 (19)	0.0200 (18)	−0.0011 (15)	0.0025 (14)	−0.0048 (15)
C10	0.0173 (18)	0.0237 (19)	0.030 (2)	−0.0039 (16)	0.0066 (15)	0.0005 (16)
C11	0.028 (2)	0.025 (2)	0.026 (2)	0.0006 (17)	0.0118 (16)	−0.0013 (16)
C12	0.0190 (18)	0.0271 (19)	0.0233 (18)	0.0047 (16)	0.0066 (15)	−0.0080 (15)
C13	0.024 (2)	0.0177 (18)	0.032 (2)	0.0002 (16)	0.0040 (16)	−0.0026 (15)
C14	0.026 (2)	0.0231 (19)	0.0244 (19)	0.0002 (17)	0.0038 (16)	0.0023 (15)
C15	0.032 (2)	0.030 (2)	0.0206 (19)	−0.0028 (18)	0.0064 (16)	−0.0060 (16)
C16	0.030 (2)	0.024 (2)	0.0187 (18)	0.0010 (17)	0.0012 (15)	−0.0032 (15)
C17	0.0218 (18)	0.0162 (17)	0.0190 (17)	0.0023 (15)	−0.0016 (14)	0.0002 (13)
C18	0.0191 (18)	0.0182 (18)	0.0230 (18)	0.0024 (15)	−0.0001 (14)	−0.0012 (15)
C19	0.0197 (18)	0.0215 (19)	0.0235 (19)	−0.0027 (16)	0.0041 (15)	0.0030 (15)
C20	0.0131 (16)	0.0261 (19)	0.0175 (17)	0.0052 (15)	0.0028 (13)	−0.0003 (14)
C21	0.0202 (18)	0.0170 (17)	0.0258 (19)	0.0036 (15)	0.0001 (15)	0.0003 (15)
C22	0.0212 (18)	0.0182 (18)	0.0201 (18)	0.0016 (15)	0.0019 (14)	0.0045 (14)

Geometric parameters (Å, º)

O1—C20	1.390 (4)	C10—H10	1.02 (4)
O1—C1	1.450 (4)	C11—C12	1.388 (5)
O2—C9	1.398 (4)	C11—H11	0.98 (3)
O2—C8	1.447 (4)	C12—C13	1.400 (5)
C1—C2	1.513 (5)	C12—C15	1.502 (5)
C1—H1A	0.99 (3)	C13—C14	1.386 (5)
C1—H1B	1.03 (4)	C13—H13	1.07 (4)
C2—C3	1.401 (5)	C14—H14	1.02 (3)
C2—C7	1.422 (5)	C15—C16	1.328 (5)
C3—C4	1.382 (6)	C15—H15	0.98 (4)
C3—H3	0.94 (4)	C16—C17	1.493 (5)
C4—C5	1.400 (6)	C16—H16	1.03 (4)
C4—H4	1.07 (4)	C17—C18	1.387 (5)
C5—C6	1.397 (5)	C17—C22	1.399 (4)
C5—H5	1.05 (4)	C18—C19	1.393 (5)
C6—C7	1.392 (5)	C18—H18	1.00 (3)
C6—H6	0.94 (4)	C19—C20	1.384 (5)
C7—C8	1.508 (5)	C19—H19	0.92 (3)
C8—H8A	1.02 (4)	C20—C21	1.387 (5)
C8—H8B	0.99 (4)	C21—C22	1.388 (5)
C9—C14	1.388 (5)	C21—H21	0.95 (3)
C9—C10	1.391 (5)	C22—H22	1.07 (3)
C10—C11	1.392 (5)
C20—O1—C1	115.6 (2)	C11—C10—H10	121.0 (19)
C9—O2—C8	112.7 (3)	C12—C11—C10	120.7 (3)
O1—C1—C2	111.9 (3)	C12—C11—H11	121 (2)
O1—C1—H1A	107 (2)	C10—C11—H11	117 (2)
C2—C1—H1A	112 (2)	C11—C12—C13	118.4 (3)
O1—C1—H1B	104 (2)	C11—C12—C15	122.6 (3)
C2—C1—H1B	109 (2)	C13—C12—C15	118.1 (3)
H1A—C1—H1B	113 (3)	C14—C13—C12	121.3 (3)
C3—C2—C7	118.4 (3)	C14—C13—H13	119.0 (18)
C3—C2—C1	116.7 (3)	C12—C13—H13	119.1 (18)
C7—C2—C1	124.8 (3)	C13—C14—C9	118.8 (3)
C4—C3—C2	122.2 (4)	C13—C14—H14	122.7 (19)
C4—C3—H3	119 (2)	C9—C14—H14	118.0 (19)
C2—C3—H3	119 (2)	C16—C15—C12	119.2 (3)
C3—C4—C5	119.4 (4)	C16—C15—H15	117 (2)
C3—C4—H4	120 (2)	C12—C15—H15	124 (2)
C5—C4—H4	121 (2)	C15—C16—C17	120.7 (3)
C6—C5—C4	119.2 (4)	C15—C16—H16	118.9 (19)
C6—C5—H5	117 (2)	C17—C16—H16	120.2 (19)
C4—C5—H5	123 (2)	C18—C17—C22	118.0 (3)
C7—C6—C5	122.0 (4)	C18—C17—C16	123.2 (3)
C7—C6—H6	124 (2)	C22—C17—C16	118.5 (3)
C5—C6—H6	114 (2)	C17—C18—C19	121.1 (3)
C6—C7—C2	118.8 (3)	C17—C18—H18	119.1 (19)
C6—C7—C8	117.8 (3)	C19—C18—H18	119.7 (19)
C2—C7—C8	123.4 (3)	C20—C19—C18	119.9 (3)
O2—C8—C7	112.7 (3)	C20—C19—H19	118 (2)
O2—C8—H8A	103 (2)	C18—C19—H19	123 (2)
C7—C8—H8A	111 (2)	C19—C20—C21	119.7 (3)
O2—C8—H8B	104 (2)	C19—C20—O1	117.9 (3)
C7—C8—H8B	114 (2)	C21—C20—O1	122.2 (3)
H8A—C8—H8B	111 (3)	C20—C21—C22	119.8 (3)
C14—C9—C10	120.6 (3)	C20—C21—H21	120 (2)
C14—C9—O2	120.9 (3)	C22—C21—H21	120 (2)
C10—C9—O2	118.4 (3)	C21—C22—C17	121.1 (3)
C9—C10—C11	119.4 (3)	C21—C22—H22	119.7 (18)
C9—C10—H10	119.6 (19)	C17—C22—H22	119.0 (18)
C20—O1—C1—C2	77.7 (4)	C10—C11—C12—C15	−161.4 (3)
O1—C1—C2—C3	59.2 (4)	C11—C12—C13—C14	−7.0 (5)
O1—C1—C2—C7	−124.0 (3)	C15—C12—C13—C14	162.8 (3)
C7—C2—C3—C4	−1.7 (5)	C12—C13—C14—C9	−0.1 (5)
C1—C2—C3—C4	175.3 (3)	C10—C9—C14—C13	6.6 (5)
C2—C3—C4—C5	−0.1 (6)	O2—C9—C14—C13	−173.0 (3)
C3—C4—C5—C6	1.0 (6)	C11—C12—C15—C16	105.4 (4)
C4—C5—C6—C7	−0.1 (6)	C13—C12—C15—C16	−64.0 (5)
C5—C6—C7—C2	−1.7 (5)	C12—C15—C16—C17	−2.1 (5)
C5—C6—C7—C8	179.9 (3)	C15—C16—C17—C18	113.3 (4)
C3—C2—C7—C6	2.5 (5)	C15—C16—C17—C22	−60.1 (5)
C1—C2—C7—C6	−174.2 (3)	C22—C17—C18—C19	5.6 (5)
C3—C2—C7—C8	−179.2 (3)	C16—C17—C18—C19	−167.9 (3)
C1—C2—C7—C8	4.0 (5)	C17—C18—C19—C20	−1.1 (5)
C9—O2—C8—C7	−87.6 (4)	C18—C19—C20—C21	−4.6 (5)
C6—C7—C8—O2	−38.4 (4)	C18—C19—C20—O1	−179.4 (3)
C2—C7—C8—O2	143.3 (3)	C1—O1—C20—C19	−135.2 (3)
C8—O2—C9—C14	79.5 (4)	C1—O1—C20—C21	50.1 (4)
C8—O2—C9—C10	−100.2 (4)	C19—C20—C21—C22	5.6 (5)
C14—C9—C10—C11	−5.7 (5)	O1—C20—C21—C22	−179.9 (3)
O2—C9—C10—C11	173.9 (3)	C20—C21—C22—C17	−0.9 (5)
C9—C10—C11—C12	−1.7 (5)	C18—C17—C22—C21	−4.6 (5)
C10—C11—C12—C13	7.9 (5)	C16—C17—C22—C21	169.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2^i	1.02 (4)	2.41 (4)	3.256 (4)	140 (3)
C1—H1B···O1^ii	1.03 (4)	2.50 (4)	3.497 (4)	161 (3)
C18—H18···CgC^iii	1.00 (3)	2.65 (4)	3.385 (4)	130 (3)

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