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The title compound, C22H22O3, demonstrates a two-photon absorption. Its metrical parameters are similar to those of related cyclo­hexa­none derivatives. In the crystal structure, two sets of centrosymmetric dimers formed by weak C—H...O inter­molecular hydrogen bonds combine to form mol­ecular tapes along [101].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601275X/lh2033sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680601275X/lh2033Isup2.hkl
Contains datablock I

CCDC reference: 608444

Key indicators

  • Single-crystal X-ray study
  • T = 103 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.116
  • Data-to-parameter ratio = 21.7

checkCIF/PLATON results

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Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.635 1.000 Tmin(prime) and Tmax expected: 0.961 0.977 RR(prime) = 0.645 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.64
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 16
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 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 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2,6-Bis(4-methoxybenzylidene)cyclohexanone top
Crystal data top
C22H22O3F(000) = 712
Mr = 334.40Dx = 1.308 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5994 reflections
a = 8.8748 (17) Åθ = 2.3–30.4°
b = 9.3854 (18) ŵ = 0.09 mm1
c = 20.698 (4) ÅT = 103 K
β = 100.074 (3)°Chunk, colorless
V = 1697.5 (6) Å30.45 × 0.35 × 0.27 mm
Z = 4
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
4979 independent reflections
Radiation source: fine-focus sealed tube3985 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 30.8°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.635, Tmax = 1.000k = 1313
19115 measured reflectionsl = 2826
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0601P)2 + 0.3366P]
where P = (Fo2 + 2Fc2)/3
4979 reflections(Δ/σ)max < 0.001
229 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.13320 (9)0.69888 (8)0.02693 (4)0.02383 (18)
O1A0.48340 (9)0.50488 (8)0.41441 (4)0.02302 (18)
O1B0.08119 (10)0.44077 (9)0.36202 (4)0.02632 (19)
C10.19480 (12)0.58159 (11)0.02571 (5)0.0182 (2)
C20.26451 (12)0.50782 (11)0.08817 (5)0.0182 (2)
C30.32304 (13)0.35694 (11)0.08520 (5)0.0223 (2)
H3A0.29830.30330.12200.027*
H3B0.43360.35900.08930.027*
C40.25510 (14)0.28144 (11)0.02172 (6)0.0242 (2)
H4A0.14620.26780.02010.029*
H4B0.30200.18830.02060.029*
C50.28126 (14)0.36793 (12)0.03765 (6)0.0241 (2)
H5A0.39030.38040.03630.029*
H5B0.24020.31640.07750.029*
C60.20544 (12)0.51180 (11)0.03882 (5)0.0187 (2)
C1A0.26939 (12)0.58510 (11)0.14364 (5)0.0179 (2)
H1AA0.22490.67480.13670.022*
C2A0.33148 (11)0.55433 (11)0.21247 (5)0.0171 (2)
C3A0.29840 (12)0.65281 (11)0.25948 (5)0.0187 (2)
H3AA0.24000.73280.24530.022*
C4A0.34990 (12)0.63425 (11)0.32585 (5)0.0190 (2)
H4AA0.32580.70090.35570.023*
C5A0.43829 (12)0.51519 (11)0.34800 (5)0.0177 (2)
C6A0.47407 (12)0.41635 (11)0.30274 (5)0.0190 (2)
H6AA0.53280.33680.31720.023*
C7A0.42213 (12)0.43651 (11)0.23607 (5)0.0188 (2)
H7AA0.44800.37040.20640.023*
C8A0.59677 (13)0.39951 (12)0.43790 (6)0.0231 (2)
H8AA0.62350.40610.48480.035*
H8AB0.68620.41550.41860.035*
H8AC0.55650.30640.42600.035*
C1B0.13932 (12)0.58198 (11)0.09346 (5)0.0184 (2)
H1BA0.09240.66750.08590.022*
C2B0.12992 (12)0.54445 (11)0.16274 (5)0.0179 (2)
C3B0.23403 (13)0.45585 (11)0.18796 (5)0.0215 (2)
H3BA0.31690.41730.15960.026*
C4B0.21453 (13)0.42554 (11)0.25429 (6)0.0225 (2)
H4BA0.28430.36660.27000.027*
C5B0.09146 (13)0.48226 (11)0.29801 (5)0.0204 (2)
C6B0.00982 (12)0.57496 (11)0.27492 (5)0.0202 (2)
H6BA0.09010.61620.30370.024*
C7B0.01123 (12)0.60477 (11)0.20801 (5)0.0192 (2)
H7BA0.05610.66710.19280.023*
C8B0.03756 (15)0.50225 (14)0.40948 (6)0.0282 (3)
H8BA0.04110.45530.45090.042*
H8BB0.01720.60180.41420.042*
H8BC0.13410.49090.39520.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0296 (4)0.0199 (4)0.0201 (4)0.0054 (3)0.0011 (3)0.0009 (3)
O1A0.0276 (4)0.0260 (4)0.0148 (4)0.0065 (3)0.0020 (3)0.0009 (3)
O1B0.0355 (5)0.0271 (4)0.0163 (4)0.0001 (3)0.0044 (3)0.0022 (3)
C10.0187 (5)0.0181 (5)0.0167 (5)0.0008 (4)0.0004 (4)0.0004 (4)
C20.0185 (5)0.0184 (5)0.0167 (5)0.0010 (4)0.0007 (4)0.0013 (4)
C30.0284 (5)0.0185 (5)0.0180 (5)0.0029 (4)0.0017 (4)0.0003 (4)
C40.0337 (6)0.0156 (5)0.0210 (5)0.0024 (4)0.0019 (5)0.0002 (4)
C50.0322 (6)0.0198 (5)0.0193 (5)0.0053 (4)0.0022 (4)0.0013 (4)
C60.0196 (5)0.0169 (5)0.0192 (5)0.0013 (4)0.0018 (4)0.0003 (4)
C1A0.0184 (5)0.0174 (4)0.0177 (5)0.0003 (4)0.0021 (4)0.0017 (4)
C2A0.0166 (5)0.0178 (5)0.0168 (5)0.0012 (3)0.0028 (4)0.0001 (4)
C3A0.0193 (5)0.0165 (5)0.0204 (5)0.0008 (4)0.0034 (4)0.0003 (4)
C4A0.0201 (5)0.0181 (5)0.0194 (5)0.0002 (4)0.0047 (4)0.0021 (4)
C5A0.0175 (5)0.0201 (5)0.0156 (5)0.0012 (4)0.0029 (4)0.0008 (4)
C6A0.0201 (5)0.0189 (5)0.0172 (5)0.0033 (4)0.0015 (4)0.0004 (4)
C7A0.0195 (5)0.0191 (5)0.0175 (5)0.0018 (4)0.0027 (4)0.0024 (4)
C8A0.0272 (5)0.0237 (5)0.0172 (5)0.0041 (4)0.0005 (4)0.0012 (4)
C1B0.0197 (5)0.0170 (5)0.0184 (5)0.0015 (4)0.0033 (4)0.0007 (4)
C2B0.0203 (5)0.0163 (4)0.0171 (5)0.0029 (4)0.0030 (4)0.0008 (4)
C3B0.0221 (5)0.0214 (5)0.0206 (5)0.0007 (4)0.0030 (4)0.0012 (4)
C4B0.0264 (5)0.0203 (5)0.0219 (5)0.0010 (4)0.0069 (4)0.0011 (4)
C5B0.0258 (5)0.0194 (5)0.0165 (5)0.0056 (4)0.0048 (4)0.0010 (4)
C6B0.0203 (5)0.0210 (5)0.0186 (5)0.0033 (4)0.0013 (4)0.0012 (4)
C7B0.0201 (5)0.0180 (5)0.0199 (5)0.0019 (4)0.0047 (4)0.0005 (4)
C8B0.0336 (6)0.0342 (6)0.0165 (5)0.0046 (5)0.0033 (5)0.0011 (4)
Geometric parameters (Å, º) top
O1—C11.2313 (13)C4A—C5A1.3958 (15)
O1A—C5A1.3663 (13)C4A—H4AA0.9300
O1A—C8A1.4338 (13)C5A—C6A1.3939 (14)
O1B—C5B1.3686 (13)C6A—C7A1.3893 (15)
O1B—C8B1.4305 (15)C6A—H6AA0.9300
C1—C21.5014 (15)C7A—H7AA0.9300
C1—C61.5053 (15)C8A—H8AA0.9600
C2—C1A1.3523 (15)C8A—H8AB0.9600
C2—C31.5132 (15)C8A—H8AC0.9600
C3—C41.5216 (15)C1B—C2B1.4648 (15)
C3—H3A0.9700C1B—H1BA0.9300
C3—H3B0.9700C2B—C7B1.4009 (15)
C4—C51.5239 (16)C2B—C3B1.4094 (15)
C4—H4A0.9700C3B—C4B1.3830 (16)
C4—H4B0.9700C3B—H3BA0.9300
C5—C61.5070 (15)C4B—C5B1.3962 (16)
C5—H5A0.9700C4B—H4BA0.9300
C5—H5B0.9700C5B—C6B1.3941 (15)
C6—C1B1.3508 (15)C6B—C7B1.3931 (15)
C1A—C2A1.4636 (15)C6B—H6BA0.9300
C1A—H1AA0.9300C7B—H7BA0.9300
C2A—C7A1.4039 (14)C8B—H8BA0.9600
C2A—C3A1.4097 (14)C8B—H8BB0.9600
C3A—C4A1.3807 (15)C8B—H8BC0.9600
C3A—H3AA0.9300
C5A—O1A—C8A117.04 (8)O1A—C5A—C4A115.86 (9)
C5B—O1B—C8B117.79 (9)C6A—C5A—C4A119.54 (10)
O1—C1—C2120.80 (9)C7A—C6A—C5A120.13 (10)
O1—C1—C6120.28 (9)C7A—C6A—H6AA119.9
C2—C1—C6118.89 (9)C5A—C6A—H6AA119.9
C1A—C2—C1115.53 (9)C6A—C7A—C2A121.54 (10)
C1A—C2—C3125.18 (10)C6A—C7A—H7AA119.2
C1—C2—C3119.29 (9)C2A—C7A—H7AA119.2
C2—C3—C4112.58 (9)O1A—C8A—H8AA109.5
C2—C3—H3A109.1O1A—C8A—H8AB109.5
C4—C3—H3A109.1H8AA—C8A—H8AB109.5
C2—C3—H3B109.1O1A—C8A—H8AC109.5
C4—C3—H3B109.1H8AA—C8A—H8AC109.5
H3A—C3—H3B107.8H8AB—C8A—H8AC109.5
C3—C4—C5110.80 (9)C6—C1B—C2B130.12 (10)
C3—C4—H4A109.5C6—C1B—H1BA114.9
C5—C4—H4A109.5C2B—C1B—H1BA114.9
C3—C4—H4B109.5C7B—C2B—C3B117.11 (10)
C5—C4—H4B109.5C7B—C2B—C1B117.71 (9)
H4A—C4—H4B108.1C3B—C2B—C1B125.15 (10)
C6—C5—C4111.09 (9)C4B—C3B—C2B120.85 (10)
C6—C5—H5A109.4C4B—C3B—H3BA119.6
C4—C5—H5A109.4C2B—C3B—H3BA119.6
C6—C5—H5B109.4C3B—C4B—C5B120.85 (10)
C4—C5—H5B109.4C3B—C4B—H4BA119.6
H5A—C5—H5B108.0C5B—C4B—H4BA119.6
C1B—C6—C1116.43 (9)O1B—C5B—C6B124.87 (10)
C1B—C6—C5125.29 (10)O1B—C5B—C4B115.53 (10)
C1—C6—C5118.21 (9)C6B—C5B—C4B119.60 (10)
C2—C1A—C2A132.17 (10)C7B—C6B—C5B118.93 (10)
C2—C1A—H1AA113.9C7B—C6B—H6BA120.5
C2A—C1A—H1AA113.9C5B—C6B—H6BA120.5
C7A—C2A—C3A116.89 (10)C6B—C7B—C2B122.55 (10)
C7A—C2A—C1A126.10 (9)C6B—C7B—H7BA118.7
C3A—C2A—C1A117.01 (9)C2B—C7B—H7BA118.7
C4A—C3A—C2A122.09 (10)O1B—C8B—H8BA109.5
C4A—C3A—H3AA119.0O1B—C8B—H8BB109.5
C2A—C3A—H3AA119.0H8BA—C8B—H8BB109.5
C3A—C4A—C5A119.80 (10)O1B—C8B—H8BC109.5
C3A—C4A—H4AA120.1H8BA—C8B—H8BC109.5
C5A—C4A—H4AA120.1H8BB—C8B—H8BC109.5
O1A—C5A—C6A124.61 (9)
O1—C1—C2—C1A6.98 (15)C3A—C4A—C5A—O1A179.57 (9)
C6—C1—C2—C1A171.22 (9)C3A—C4A—C5A—C6A0.21 (15)
O1—C1—C2—C3173.09 (10)O1A—C5A—C6A—C7A179.82 (10)
C6—C1—C2—C38.72 (14)C4A—C5A—C6A—C7A0.07 (16)
C1A—C2—C3—C4160.36 (11)C5A—C6A—C7A—C2A0.87 (16)
C1—C2—C3—C419.71 (14)C3A—C2A—C7A—C6A1.33 (15)
C2—C3—C4—C554.58 (13)C1A—C2A—C7A—C6A179.28 (10)
C3—C4—C5—C661.02 (13)C1—C6—C1B—C2B179.64 (10)
O1—C1—C6—C1B2.51 (15)C5—C6—C1B—C2B3.38 (18)
C2—C1—C6—C1B179.28 (9)C6—C1B—C2B—C7B156.95 (11)
O1—C1—C6—C5179.72 (10)C6—C1B—C2B—C3B25.27 (17)
C2—C1—C6—C52.08 (14)C7B—C2B—C3B—C4B2.82 (15)
C4—C5—C6—C1B144.72 (11)C1B—C2B—C3B—C4B179.39 (10)
C4—C5—C6—C132.21 (14)C2B—C3B—C4B—C5B0.19 (16)
C1—C2—C1A—C2A177.62 (10)C8B—O1B—C5B—C6B3.29 (15)
C3—C2—C1A—C2A2.31 (19)C8B—O1B—C5B—C4B176.42 (9)
C2—C1A—C2A—C7A9.04 (18)C3B—C4B—C5B—O1B177.81 (10)
C2—C1A—C2A—C3A171.58 (11)C3B—C4B—C5B—C6B2.46 (16)
C7A—C2A—C3A—C4A1.06 (15)O1B—C5B—C6B—C7B177.97 (9)
C1A—C2A—C3A—C4A179.50 (9)C4B—C5B—C6B—C7B2.33 (15)
C2A—C3A—C4A—C5A0.31 (16)C5B—C6B—C7B—C2B0.42 (15)
C8A—O1A—C5A—C6A11.52 (15)C3B—C2B—C7B—C6B2.95 (15)
C8A—O1A—C5A—C4A168.72 (9)C1B—C2B—C7B—C6B179.08 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O1i0.972.523.4220 (16)155
C8A—H8AA···O1Aii0.962.583.3789 (15)141
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1.
 

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