4,5,12,13-Tetra­acet­yl[2.2]paracyclo­phane

The title compound, C₂₄H₂₄O₄, crystallizes with two independent mol­ecules, both with crystallographic inversion symmetry. The acetyl groups are rotated out of the ring planes, with the O atoms directed towards the inside of the mol­ecules. Two C—H...O and one C—H...π inter­action link the mol­ecules into layers parallel to the ac plane.

Key indicators

• Single-crystal X-ray study
• T = 133 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.047
• wR factor = 0.132
• Data-to-parameter ratio = 21.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10D   ..  O1      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A    ..  O1'     ..       2.67 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

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

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

4,5,12,13-Tetraacetyl[2.2]paracyclophane

Crystal data

C24H24O4	F(000) = 800
Mr = 376.43	Dx = 1.346 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0251 (8) Å	Cell parameters from 4056 reflections
b = 14.8898 (14) Å	θ = 2.6–30.5°
c = 15.5679 (16) Å	µ = 0.09 mm^−1
β = 93.163 (4)°	T = 133 K
V = 1857.4 (3) Å^3	Irregular tablet, pale yellow
Z = 4	0.45 × 0.25 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	3718 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
Graphite monochromator	θmax = 30.0°, θmin = 1.9°
Detector resolution: 8.192 pixels mm^-1	h = −11→7
ω scans	k = −20→18
14863 measured reflections	l = −20→21
5422 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0722P)^2] where P = (Fo^2 + 2Fc^2)/3
5422 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 6.0634 (0.0031) x - 0.2063 (0.0145) y + 10.8295 (0.0064) z = 1.4419 (0.0072)

* 0.0106 (0.0007) C4 * -0.0105 (0.0007) C5 * 0.0107 (0.0007) C7 * -0.0108 (0.0007) C8 - 0.1671 (0.0020) C3 - 0.1639 (0.0020) C6

Rms deviation of fitted atoms = 0.0106

5.6953 (0.0030) x + 3.9815 (0.0124) y + 9.5220 (0.0082) z = 4.3992 (0.0016)

Angle to previous plane (with approximate e.s.d.) = 83.51 (0.04)

* 0.0108 (0.0006) C4' * -0.0108 (0.0006) C5' * 0.0110 (0.0006) C7' * -0.0110 (0.0006) C8' -0.1741 (0.0019) C3' -0.1631 (0.0019) C6'

Rms deviation of fitted atoms = 0.0109

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
C1	0.09918 (18)	0.31576 (9)	−0.02638 (9)	0.0216 (3)
H1A	0.2035	0.2928	0.0026	0.026*
H1B	0.0716	0.2768	−0.0767	0.026*
C2	−0.04692 (18)	0.30943 (9)	0.03821 (9)	0.0216 (3)
H2A	−0.1409	0.2751	0.0106	0.026*
H2B	−0.0063	0.2762	0.0903	0.026*
C3	−0.10896 (16)	0.40070 (9)	0.06434 (9)	0.0175 (3)
C4	−0.02548 (16)	0.45300 (9)	0.12848 (8)	0.0158 (3)
C5	−0.03272 (16)	0.54727 (9)	0.12428 (8)	0.0160 (3)
C6	−0.12846 (17)	0.58981 (9)	0.05732 (9)	0.0179 (3)
C7	−0.24160 (17)	0.53601 (9)	0.00907 (9)	0.0194 (3)
H7	−0.3277	0.5636	−0.0261	0.023*
C8	−0.23033 (17)	0.44349 (9)	0.01164 (9)	0.0201 (3)
H8	−0.3066	0.4085	−0.0231	0.024*
C9	0.09628 (17)	0.40941 (9)	0.19288 (9)	0.0176 (3)
C10	0.03353 (19)	0.33682 (10)	0.24989 (10)	0.0253 (3)
H10A	0.1171	0.2889	0.2563	0.030*
H10B	−0.0708	0.3122	0.2240	0.030*
H10C	0.0134	0.3620	0.3065	0.030*
C11	0.06617 (16)	0.60343 (9)	0.18930 (9)	0.0176 (3)
C12	0.03697 (18)	0.58864 (10)	0.28294 (9)	0.0217 (3)
H12A	0.1425	0.5956	0.3171	0.026*
H12B	−0.0067	0.5279	0.2909	0.026*
H12C	−0.0439	0.6328	0.3018	0.026*
O1	0.23997 (12)	0.43515 (7)	0.19997 (7)	0.0240 (2)
O2	0.15805 (13)	0.66325 (6)	0.16661 (7)	0.0243 (2)
C1'	0.42977 (17)	0.15015 (9)	−0.11284 (9)	0.0197 (3)
H1'1	0.3324	0.1889	−0.1029	0.024*
H1'2	0.4570	0.1574	−0.1737	0.024*
C2'	0.58404 (17)	0.18332 (9)	−0.05283 (9)	0.0209 (3)
H2'1	0.6804	0.1943	−0.0885	0.025*
H2'2	0.5552	0.2409	−0.0255	0.025*
C3'	0.63334 (16)	0.11544 (9)	0.01663 (8)	0.0173 (3)
C4'	0.54619 (16)	0.10583 (9)	0.09219 (8)	0.0171 (3)
C5'	0.53548 (16)	0.02089 (9)	0.13185 (8)	0.0168 (3)
C6'	0.61771 (16)	−0.05338 (9)	0.09772 (8)	0.0173 (3)
C7'	0.73640 (16)	−0.03620 (9)	0.03783 (9)	0.0189 (3)
H7'	0.8139	−0.0817	0.0247	0.023*
C8'	0.74295 (17)	0.04657 (9)	−0.00300 (9)	0.0196 (3)
H8'	0.8230	0.0564	−0.0448	0.023*
C9'	0.44727 (17)	0.18400 (9)	0.12400 (9)	0.0192 (3)
C10'	0.54328 (19)	0.26622 (10)	0.15295 (10)	0.0270 (3)
H10D	0.4651	0.3148	0.1645	0.032*
H10E	0.6160	0.2850	0.1077	0.032*
H10F	0.6113	0.2525	0.2055	0.032*
C11'	0.42833 (17)	0.00777 (9)	0.20728 (9)	0.0190 (3)
C12'	0.45373 (18)	0.06768 (10)	0.28492 (9)	0.0233 (3)
H12D	0.3600	0.1097	0.2869	0.028*
H12E	0.5579	0.1014	0.2811	0.028*
H12F	0.4598	0.0309	0.3372	0.028*
O1'	0.29698 (12)	0.17885 (7)	0.12881 (7)	0.0269 (2)
O2'	0.32709 (13)	−0.05331 (7)	0.20705 (7)	0.0269 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0251 (7)	0.0195 (7)	0.0202 (7)	0.0061 (5)	0.0016 (5)	0.0014 (5)
C2	0.0271 (8)	0.0179 (7)	0.0197 (7)	−0.0045 (6)	0.0013 (5)	−0.0006 (5)
C3	0.0171 (7)	0.0190 (6)	0.0166 (6)	−0.0039 (5)	0.0036 (5)	0.0002 (5)
C4	0.0150 (6)	0.0185 (7)	0.0143 (6)	−0.0007 (5)	0.0028 (5)	0.0004 (5)
C5	0.0148 (6)	0.0189 (7)	0.0147 (6)	0.0010 (5)	0.0032 (5)	−0.0008 (5)
C6	0.0179 (7)	0.0199 (7)	0.0163 (6)	0.0041 (5)	0.0046 (5)	0.0001 (5)
C7	0.0159 (6)	0.0281 (7)	0.0142 (6)	0.0043 (5)	0.0024 (5)	0.0014 (5)
C8	0.0166 (6)	0.0280 (7)	0.0159 (6)	−0.0044 (5)	0.0020 (5)	−0.0012 (5)
C9	0.0206 (7)	0.0157 (6)	0.0164 (6)	0.0016 (5)	0.0008 (5)	−0.0033 (5)
C10	0.0297 (8)	0.0232 (7)	0.0225 (8)	−0.0007 (6)	−0.0022 (6)	0.0057 (6)
C11	0.0181 (7)	0.0155 (6)	0.0191 (7)	0.0045 (5)	0.0005 (5)	−0.0009 (5)
C12	0.0237 (7)	0.0240 (7)	0.0174 (7)	0.0031 (6)	0.0000 (5)	−0.0030 (5)
O1	0.0202 (5)	0.0281 (5)	0.0235 (6)	−0.0013 (4)	−0.0017 (4)	0.0003 (4)
O2	0.0276 (6)	0.0192 (5)	0.0261 (6)	−0.0033 (4)	0.0020 (4)	−0.0010 (4)
C1'	0.0202 (7)	0.0214 (7)	0.0174 (7)	0.0013 (5)	−0.0002 (5)	0.0008 (5)
C2'	0.0243 (7)	0.0204 (7)	0.0182 (7)	−0.0046 (6)	0.0019 (5)	0.0013 (5)
C3'	0.0160 (6)	0.0217 (7)	0.0140 (6)	−0.0057 (5)	−0.0006 (5)	−0.0006 (5)
C4'	0.0139 (6)	0.0211 (7)	0.0159 (6)	−0.0016 (5)	−0.0011 (5)	−0.0017 (5)
C5'	0.0132 (6)	0.0230 (7)	0.0140 (6)	−0.0028 (5)	−0.0007 (5)	−0.0003 (5)
C6'	0.0151 (6)	0.0220 (7)	0.0144 (6)	0.0002 (5)	−0.0035 (5)	0.0004 (5)
C7'	0.0148 (6)	0.0245 (7)	0.0172 (7)	0.0003 (5)	−0.0016 (5)	−0.0035 (5)
C8'	0.0152 (6)	0.0269 (7)	0.0168 (7)	−0.0046 (5)	0.0023 (5)	−0.0021 (5)
C9'	0.0212 (7)	0.0214 (7)	0.0151 (6)	0.0005 (5)	0.0019 (5)	0.0022 (5)
C10'	0.0293 (8)	0.0234 (7)	0.0287 (8)	−0.0029 (6)	0.0059 (6)	−0.0053 (6)
C11'	0.0166 (7)	0.0237 (7)	0.0167 (7)	0.0035 (5)	0.0008 (5)	0.0029 (5)
C12'	0.0220 (7)	0.0319 (8)	0.0164 (7)	0.0028 (6)	0.0035 (5)	−0.0013 (6)
O1'	0.0189 (5)	0.0283 (6)	0.0337 (6)	0.0027 (4)	0.0040 (4)	0.0010 (4)
O2'	0.0263 (6)	0.0298 (6)	0.0251 (6)	−0.0065 (4)	0.0066 (4)	0.0018 (4)

Geometric parameters (Å, º)

C1—C6^i	1.5089 (19)	C1'—C6'^ii	1.5121 (19)
C1—C2	1.589 (2)	C1'—C2'	1.5881 (18)
C1—H1A	0.9900	C1'—H1'1	0.9900
C1—H1B	0.9900	C1'—H1'2	0.9900
C2—C3	1.5108 (19)	C2'—C3'	1.5165 (18)
C2—H2A	0.9900	C2'—H2'1	0.9900
C2—H2B	0.9900	C2'—H2'2	0.9900
C3—C8	1.3927 (18)	C3'—C8'	1.3958 (19)
C3—C4	1.4066 (18)	C3'—C4'	1.4087 (19)
C4—C5	1.4063 (18)	C4'—C5'	1.4120 (19)
C4—C9	1.5077 (18)	C4'—C9'	1.5078 (19)
C5—C6	1.4106 (18)	C5'—C6'	1.4070 (19)
C5—C11	1.5050 (18)	C5'—C11'	1.5059 (19)
C6—C7	1.3982 (19)	C6'—C7'	1.3928 (19)
C7—C8	1.381 (2)	C7'—C8'	1.3890 (19)
C7—H7	0.9500	C7'—H7'	0.9500
C8—H8	0.9500	C8'—H8'	0.9500
C9—O1	1.2144 (16)	C9'—O1'	1.2150 (16)
C9—C10	1.5029 (19)	C9'—C10'	1.5024 (19)
C10—H10A	0.9800	C10'—H10D	0.9800
C10—H10B	0.9800	C10'—H10E	0.9800
C10—H10C	0.9800	C10'—H10F	0.9800
C11—O2	1.2209 (16)	C11'—O2'	1.2194 (16)
C11—C12	1.5055 (19)	C11'—C12'	1.5069 (19)
C12—H12A	0.9800	C12'—H12D	0.9800
C12—H12B	0.9800	C12'—H12E	0.9800
C12—H12C	0.9800	C12'—H12F	0.9800
C6^i—C1—C2	112.99 (11)	C6'^ii—C1'—C2'	113.56 (11)
C6^i—C1—H1A	109.0	C6'^ii—C1'—H1'1	108.9
C2—C1—H1A	109.0	C2'—C1'—H1'1	108.9
C6^i—C1—H1B	109.0	C6'^ii—C1'—H1'2	108.9
C2—C1—H1B	109.0	C2'—C1'—H1'2	108.9
H1A—C1—H1B	107.8	H1'1—C1'—H1'2	107.7
C3—C2—C1	112.50 (11)	C3'—C2'—C1'	112.11 (11)
C3—C2—H2A	109.1	C3'—C2'—H2'1	109.2
C1—C2—H2A	109.1	C1'—C2'—H2'1	109.2
C3—C2—H2B	109.1	C3'—C2'—H2'2	109.2
C1—C2—H2B	109.1	C1'—C2'—H2'2	109.2
H2A—C2—H2B	107.8	H2'1—C2'—H2'2	107.9
C8—C3—C4	117.07 (12)	C8'—C3'—C4'	117.13 (12)
C8—C3—C2	118.88 (12)	C8'—C3'—C2'	118.45 (12)
C4—C3—C2	122.55 (12)	C4'—C3'—C2'	122.76 (12)
C5—C4—C3	120.18 (12)	C3'—C4'—C5'	120.08 (12)
C5—C4—C9	118.97 (11)	C3'—C4'—C9'	119.37 (12)
C3—C4—C9	119.97 (12)	C5'—C4'—C9'	120.13 (12)
C4—C5—C6	120.13 (12)	C6'—C5'—C4'	119.85 (12)
C4—C5—C11	120.29 (11)	C6'—C5'—C11'	119.50 (12)
C6—C5—C11	119.54 (12)	C4'—C5'—C11'	120.55 (12)
C7—C6—C5	116.80 (12)	C7'—C6'—C5'	117.43 (12)
C7—C6—C1^i	118.06 (12)	C7'—C6'—C1'^ii	117.82 (12)
C5—C6—C1^i	124.49 (12)	C5'—C6'—C1'^ii	124.25 (13)
C8—C7—C6	121.09 (12)	C8'—C7'—C6'	120.92 (13)
C8—C7—H7	119.5	C8'—C7'—H7'	119.5
C6—C7—H7	119.5	C6'—C7'—H7'	119.5
C7—C8—C3	121.06 (12)	C7'—C8'—C3'	120.76 (13)
C7—C8—H8	119.5	C7'—C8'—H8'	119.6
C3—C8—H8	119.5	C3'—C8'—H8'	119.6
O1—C9—C10	121.38 (12)	O1'—C9'—C10'	121.82 (13)
O1—C9—C4	120.12 (12)	O1'—C9'—C4'	120.93 (12)
C10—C9—C4	118.44 (12)	C10'—C9'—C4'	117.19 (12)
C9—C10—H10A	109.5	C9'—C10'—H10D	109.5
C9—C10—H10B	109.5	C9'—C10'—H10E	109.5
H10A—C10—H10B	109.5	H10D—C10'—H10E	109.5
C9—C10—H10C	109.5	C9'—C10'—H10F	109.5
H10A—C10—H10C	109.5	H10D—C10'—H10F	109.5
H10B—C10—H10C	109.5	H10E—C10'—H10F	109.5
O2—C11—C5	121.01 (12)	O2'—C11'—C5'	120.23 (12)
O2—C11—C12	121.04 (12)	O2'—C11'—C12'	120.29 (13)
C5—C11—C12	117.74 (12)	C5'—C11'—C12'	119.40 (12)
C11—C12—H12A	109.5	C11'—C12'—H12D	109.5
C11—C12—H12B	109.5	C11'—C12'—H12E	109.5
H12A—C12—H12B	109.5	H12D—C12'—H12E	109.5
C11—C12—H12C	109.5	C11'—C12'—H12F	109.5
H12A—C12—H12C	109.5	H12D—C12'—H12F	109.5
H12B—C12—H12C	109.5	H12E—C12'—H12F	109.5
C6^i—C1—C2—C3	−7.95 (16)	C6'^ii—C1'—C2'—C3'	−9.15 (17)
C1—C2—C3—C8	85.16 (15)	C1'—C2'—C3'—C8'	86.03 (15)
C1—C2—C3—C4	−80.49 (16)	C1'—C2'—C3'—C4'	−78.84 (16)
C8—C3—C4—C5	−16.33 (19)	C8'—C3'—C4'—C5'	−16.98 (18)
C2—C3—C4—C5	149.56 (13)	C2'—C3'—C4'—C5'	148.08 (12)
C8—C3—C4—C9	174.54 (12)	C8'—C3'—C4'—C9'	170.48 (11)
C2—C3—C4—C9	−19.56 (19)	C2'—C3'—C4'—C9'	−24.46 (18)
C3—C4—C5—C6	2.2 (2)	C3'—C4'—C5'—C6'	2.57 (18)
C9—C4—C5—C6	171.42 (12)	C9'—C4'—C5'—C6'	175.05 (11)
C3—C4—C5—C11	−175.70 (12)	C3'—C4'—C5'—C11'	−173.74 (12)
C9—C4—C5—C11	−6.46 (19)	C9'—C4'—C5'—C11'	−1.26 (18)
C4—C5—C6—C7	13.94 (19)	C4'—C5'—C6'—C7'	14.00 (18)
C11—C5—C6—C7	−168.16 (12)	C11'—C5'—C6'—C7'	−169.65 (11)
C4—C5—C6—C1^i	−156.55 (13)	C4'—C5'—C6'—C1'^ii	−157.70 (12)
C11—C5—C6—C1^i	21.3 (2)	C11'—C5'—C6'—C1'^ii	18.65 (19)
C5—C6—C7—C8	−16.1 (2)	C5'—C6'—C7'—C8'	−16.25 (19)
C1^i—C6—C7—C8	154.98 (13)	C1'^ii—C6'—C7'—C8'	155.99 (12)
C6—C7—C8—C3	1.9 (2)	C6'—C7'—C8'—C3'	1.65 (19)
C4—C3—C8—C7	14.4 (2)	C4'—C3'—C8'—C7'	15.01 (18)
C2—C3—C8—C7	−152.01 (13)	C2'—C3'—C8'—C7'	−150.71 (12)
C5—C4—C9—O1	−46.88 (18)	C3'—C4'—C9'—O1'	117.58 (15)
C3—C4—C9—O1	122.37 (14)	C5'—C4'—C9'—O1'	−54.95 (18)
C5—C4—C9—C10	130.57 (14)	C3'—C4'—C9'—C10'	−65.10 (16)
C3—C4—C9—C10	−60.17 (17)	C5'—C4'—C9'—C10'	122.37 (14)
C4—C5—C11—O2	128.21 (14)	C6'—C5'—C11'—O2'	−47.41 (18)
C6—C5—C11—O2	−49.69 (18)	C4'—C5'—C11'—O2'	128.92 (14)
C4—C5—C11—C12	−56.87 (17)	C6'—C5'—C11'—C12'	129.37 (13)
C6—C5—C11—C12	125.23 (14)	C4'—C5'—C11'—C12'	−54.30 (17)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10′—H10D···O1	0.98	2.63	3.6033 (18)	176
C1—H1A···O1′	0.99	2.67	3.4770 (17)	139
C12′—H12E···O2^iii	0.98	2.55	3.4701 (18)	156
C12—H12C···O1′^iv	0.98	2.45	3.3586 (18)	154

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