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As part of an ongoing series of experimental charge-density investigations into the intra- and intermolecular interactions present in compounds which undergo solid-state [2 + 2] cycloaddition reactions, the charge-density analyses of trans-cinnamic acid and coumarin-3-carboxylic acid are reported. Thus, high-resolution single-crystal X-ray diffraction data were recorded at 100 K for trans-cinnamic acid (sin θ/λmax = 1.03 Å−1) and coumarin-3-carboxylic acid (sin θ/λmax = 1.19 Å−1). In addition to the anticipated O—H...O hydrogen bonds weak C—H...O interactions were identified in both structures along with very weak intermolecular interactions between pairs of molecules that undergo solid-state [2 + 2] cycloaddition reactions upon irradiation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109001566/so5021sup1.cif
Contains datablocks 2a, publication_text, 1a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109001566/so50211asup2.hkl
Contains datablock 1a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109001566/so50212asup3.hkl
Contains datablock 2a

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768109001566/so5021sup4.pdf
Hirshfeld analysis results and extra figures

CCDC references: 737459; 737460

Computing details top

For both compounds, data collection: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET) (compiled Apr 18 2008,18:17:43); cell refinement: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET) (compiled Apr 18 2008,18:17:43); data reduction: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET) (compiled Apr 18 2008,18:17:43). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for (1a); SHELXS97 (Sheldrick, 1998) for (2a). For both compounds, program(s) used to refine structure: Volkov et al., (2006); molecular graphics: Volkov et al., (2006); software used to prepare material for publication: Volkov et al., (2006).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
(1a) top
Crystal data top
C9H8O2F(000) = 312
Mr = 148.15Dx = 1.318 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 38572 reflections
a = 5.5504 (1) Åθ = 2.3–49.3°
b = 17.5427 (1) ŵ = 0.09 mm1
c = 7.7161 (1) ÅT = 100 K
β = 96.296 (1)°Block, colourless
V = 746.78 (2) Å30.57 × 0.36 × 0.10 mm
Z = 4
Data collection top
Goniometer Xcalibur, detector: Atlas (Gemini ultra Mo)
diffractometer
6591 independent reflections
Radiation source: Enhance (Mo) X-ray Source4859 reflections with I > 3 σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 10.3317 pixels mm-1θmax = 46.5°, θmin = 2.3°
ω scansh = 119
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET) (compiled Apr 18 2008,18:17:43) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 3534
Tmin = 0.911, Tmax = 0.990l = 1515
70528 measured reflections
Refinement top
Refinement on F0 restraints
Least-squares matrix: fullOnly H-atom displacement parameters refined
R[F2 > 2σ(F2)] = 0.018 w1 = 1/[s2(Fo)]
wR(F2) = 0.014(Δ/σ)max < 0.001
S = 1.74Δρmax = 0.13 e Å3
4859 reflectionsΔρmin = 0.13 e Å3
295 parameters
Crystal data top
C9H8O2V = 746.78 (2) Å3
Mr = 148.15Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.5504 (1) ŵ = 0.09 mm1
b = 17.5427 (1) ÅT = 100 K
c = 7.7161 (1) Å0.57 × 0.36 × 0.10 mm
β = 96.296 (1)°
Data collection top
Goniometer Xcalibur, detector: Atlas (Gemini ultra Mo)
diffractometer
6591 independent reflections
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET) (compiled Apr 18 2008,18:17:43) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
4859 reflections with I > 3 σ(I)
Tmin = 0.911, Tmax = 0.990Rint = 0.023
70528 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0180 restraints
wR(F2) = 0.014Only H-atom displacement parameters refined
S = 1.74Δρmax = 0.13 e Å3
4859 reflectionsΔρmin = 0.13 e Å3
295 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O(1)0.26803 (7)0.04975 (2)0.58236 (4)0.022
O(2)0.05071 (7)0.00677 (2)0.71005 (4)0.021
C(1)0.53321 (5)0.119200 (14)1.22626 (3)0.018
C(2)0.66266 (6)0.148390 (16)1.37622 (3)0.023
C(3)0.87407 (6)0.190256 (16)1.36564 (4)0.023
C(4)0.95498 (5)0.203295 (15)1.20338 (4)0.021
C(5)0.82592 (5)0.174013 (14)1.05311 (3)0.018
C(6)0.61359 (4)0.131561 (12)1.06228 (3)0.015
C(7)0.48321 (5)0.102155 (13)0.90102 (3)0.016
C(8)0.27040 (5)0.064820 (14)0.88698 (3)0.016
C(9)0.15126 (5)0.038215 (14)0.71843 (3)0.016
H(1A)0.1745980.0272140.474750.037
H(1)0.3732820.0850461.2356880.035
H(2)0.5981730.1381291.5012130.043
H(3)0.9751370.2128491.4819180.04
H(4)1.1179380.235731.1922030.042
H(5)0.894590.1841650.9295060.035
H(7)0.5709810.1135950.7855680.031
H(8)0.1798640.0540761.0015130.033
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(1)0.02249 (14)0.03106 (15)0.01370 (11)0.00881 (12)0.00264 (10)0.00048 (10)
O(2)0.01632 (12)0.03081 (14)0.01686 (10)0.00703 (11)0.00132 (9)0.00244 (10)
C(1)0.01862 (10)0.02038 (9)0.01571 (9)0.00558 (8)0.00264 (8)0.00201 (7)
C(2)0.02602 (13)0.02506 (11)0.01650 (9)0.00874 (10)0.00237 (9)0.00422 (8)
C(3)0.02465 (13)0.02234 (11)0.02113 (10)0.00771 (9)0.00098 (10)0.00361 (9)
C(4)0.01763 (11)0.02044 (10)0.02434 (11)0.00563 (8)0.00030 (9)0.00010 (9)
C(5)0.01480 (9)0.01875 (9)0.01960 (9)0.00248 (8)0.00183 (8)0.00148 (8)
C(6)0.01417 (9)0.01494 (8)0.01537 (8)0.00119 (7)0.00151 (7)0.00013 (7)
C(7)0.01570 (9)0.01803 (9)0.01444 (8)0.00178 (7)0.00107 (7)0.00037 (7)
C(8)0.01544 (9)0.01899 (9)0.01456 (8)0.00209 (8)0.00159 (7)0.00100 (7)
C(9)0.01513 (10)0.01985 (9)0.01421 (8)0.00228 (8)0.00106 (7)0.00031 (7)
H(1A)0.0375150.0517370.0214350.0028390.0013080.014456
H(1)0.033570.043220.0297410.0040830.007390.017817
H(2)0.0466170.0589750.0234480.0056780.00770.02197
H(3)0.0408040.0472550.0307530.0073440.005340.015975
H(4)0.0400240.0433080.0417760.0012220.0014280.01691
H(5)0.029950.0472210.0287830.0016540.008170.01242
H(7)0.0276020.0427090.0236820.002130.0086110.008558
H(8)0.0328890.0438910.0244790.0031640.0102160.008228
Geometric parameters (Å, º) top
O(1)—C(9)1.3087 (4)C(4)—C(5)1.3926 (4)
O(1)—H(1A)1.0100C(4)—H(4)1.0800
O(2)—C(9)1.2447 (4)C(5)—C(6)1.4024 (3)
C(1)—C(2)1.3911 (3)C(5)—H(5)1.0800
C(1)—C(6)1.4038 (3)C(6)—C(7)1.4630 (3)
C(1)—H(1)1.0800C(7)—C(8)1.3446 (3)
C(2)—C(3)1.3943 (4)C(7)—H(7)1.0800
C(2)—H(2)1.0800C(8)—C(9)1.4690 (3)
C(3)—C(4)1.3946 (4)C(8)—H(8)1.0800
C(3)—H(3)1.0800
C(9)—O(1)—H(1A)110.14C(4)—C(5)—H(5)118.38
C(2)—C(1)—C(6)120.44 (2)C(6)—C(5)—H(5)120.80
C(2)—C(1)—H(1)120.10C(1)—C(6)—C(5)118.64 (2)
C(6)—C(1)—H(1)119.42C(1)—C(6)—C(7)122.39 (2)
C(1)—C(2)—C(3)120.43 (3)C(5)—C(6)—C(7)118.97 (2)
C(1)—C(2)—H(2)119.34C(6)—C(7)—C(8)126.05 (2)
C(3)—C(2)—H(2)120.24C(6)—C(7)—H(7)114.22
C(2)—C(3)—C(4)119.66 (3)C(8)—C(7)—H(7)119.72
C(2)—C(3)—H(3)120.56C(7)—C(8)—C(9)122.16 (2)
C(4)—C(3)—H(3)119.77C(7)—C(8)—H(8)120.17
C(3)—C(4)—C(5)120.01 (2)C(9)—C(8)—H(8)117.67
C(3)—C(4)—H(4)120.87O(1)—C(9)—O(2)123.32 (3)
C(5)—C(4)—H(4)119.12O(1)—C(9)—C(8)116.54 (3)
C(4)—C(5)—C(6)120.81 (2)O(2)—C(9)—C(8)120.15 (2)
H(1A)—O(1)—C(9)—O(2)2.92C(3)—C(4)—C(5)—H(5)178.93
H(1A)—O(1)—C(9)—C(8)177.31H(4)—C(4)—C(5)—C(6)179.95
C(6)—C(1)—C(2)—C(3)0.05 (3)H(4)—C(4)—C(5)—H(5)0.74
C(2)—C(1)—C(6)—C(5)0.20 (2)C(4)—C(5)—C(6)—C(1)0.09 (2)
C(2)—C(1)—C(6)—C(7)179.85 (4)C(4)—C(5)—C(6)—C(7)179.75 (4)
C(6)—C(1)—C(2)—H(2)179.82H(5)—C(5)—C(6)—C(1)179.28
H(1)—C(1)—C(2)—C(3)177.72H(5)—C(5)—C(6)—C(7)1.06
H(1)—C(1)—C(2)—H(2)2.05C(1)—C(6)—C(7)—C(8)4.06 (2)
H(1)—C(1)—C(6)—C(5)177.99C(1)—C(6)—C(7)—H(7)177.03
H(1)—C(1)—C(6)—C(7)2.36C(5)—C(6)—C(7)—C(8)175.58 (4)
C(1)—C(2)—C(3)—C(4)0.43 (3)C(5)—C(6)—C(7)—H(7)3.32
C(1)—C(2)—C(3)—H(3)179.84C(6)—C(7)—C(8)—C(9)179.17 (4)
H(2)—C(2)—C(3)—C(4)179.81C(6)—C(7)—C(8)—H(8)0.02
H(2)—C(2)—C(3)—H(3)0.07H(7)—C(7)—C(8)—C(9)0.32
C(2)—C(3)—C(4)—C(5)0.54 (3)H(7)—C(7)—C(8)—H(8)178.87
C(2)—C(3)—C(4)—H(4)179.80C(7)—C(8)—C(9)—O(1)2.88 (3)
H(3)—C(3)—C(4)—C(5)179.72C(7)—C(8)—C(9)—O(2)176.90 (4)
H(3)—C(3)—C(4)—H(4)0.06H(8)—C(8)—C(9)—O(1)177.91
C(3)—C(4)—C(5)—C(6)0.28 (3)H(8)—C(8)—C(9)—O(2)2.31
(2a) top
Crystal data top
C10H6O4F(000) = 392
Mr = 190.15Dx = 1.574 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 66859 reflections
a = 11.1992 (1) Åθ = 3.1–67.4°
b = 5.4662 (1) ŵ = 0.12 mm1
c = 13.7267 (2) ÅT = 100 K
β = 107.256 (1)°Block, colourless
V = 802.49 (2) Å30.60 × 0.52 × 0.29 mm
Z = 4
Data collection top
Goniometer Xcalibur, detector: Atlas (Gemini ultra Mo)
diffractometer
11309 independent reflections
Radiation source: Enhance (Mo) X-ray Source8933 reflections with I > 3 σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 10.3317 pixels mm-1θmax = 57.8°, θmin = 3.1°
CCD scansh = 2626
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.18 (release 23-07-2008 CrysAlis171 .NET) (compiled Jul 23 2008,18:57:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1313
Tmin = 0.891, Tmax = 0.965l = 3232
147662 measured reflections
Refinement top
Refinement on F367 parameters
Least-squares matrix: full0 restraints
R[F2 > 2σ(F2)] = 0.016 w1 = 1/[s2(Fo)]
wR(F2) = 0.014(Δ/σ)max < 0.001
S = 1.67Δρmax = 0.15 e Å3
8933 reflectionsΔρmin = 0.14 e Å3
Crystal data top
C10H6O4V = 802.49 (2) Å3
Mr = 190.15Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.1992 (1) ŵ = 0.12 mm1
b = 5.4662 (1) ÅT = 100 K
c = 13.7267 (2) Å0.60 × 0.52 × 0.29 mm
β = 107.256 (1)°
Data collection top
Goniometer Xcalibur, detector: Atlas (Gemini ultra Mo)
diffractometer
11309 independent reflections
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.18 (release 23-07-2008 CrysAlis171 .NET) (compiled Jul 23 2008,18:57:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
8933 reflections with I > 3 σ(I)
Tmin = 0.891, Tmax = 0.965Rint = 0.023
147662 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.016367 parameters
wR(F2) = 0.0140 restraints
S = 1.67Δρmax = 0.15 e Å3
8933 reflectionsΔρmin = 0.14 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O(1)0.900004 (14)0.19923 (2)0.254215 (12)0.012
O(2)0.772812 (16)0.30671 (3)0.341479 (13)0.015
O(3)0.73811 (2)0.03092 (4)0.483840 (17)0.021
O(4)0.856569 (19)0.29867 (3)0.528735 (15)0.018
C(1)0.980824 (12)0.03660 (2)0.230834 (10)0.011
C(2)1.023635 (14)0.09363 (2)0.148238 (12)0.014
C(3)1.106404 (15)0.06761 (3)0.123505 (12)0.015
C(4)1.146074 (15)0.28187 (3)0.180257 (13)0.015
C(5)1.102190 (13)0.33595 (2)0.262115 (12)0.013
C(6)1.017881 (12)0.17668 (2)0.288303 (10)0.01
C(7)0.965884 (12)0.22503 (2)0.369680 (10)0.011
C(8)0.881696 (12)0.06819 (2)0.389306 (10)0.01
C(9)0.846586 (12)0.15328 (2)0.328619 (10)0.011
C(10)0.825109 (14)0.12314 (2)0.472765 (11)0.013
H(3A)0.7302010.1626940.4307150.028
H(2)0.9930410.2565040.1032110.031
H(3)1.1400670.0237080.0595630.034
H(4)1.2096620.4081840.1609280.034
H(5)1.1309510.5007650.3062340.03
H(7)0.99720.3840990.417040.027
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(1)0.01327 (4)0.01043 (3)0.01187 (4)0.00072 (3)0.00434 (4)0.00192 (3)
O(2)0.01680 (5)0.01453 (4)0.01584 (5)0.00562 (4)0.00607 (4)0.00173 (4)
O(3)0.02272 (7)0.02447 (6)0.01944 (7)0.00838 (6)0.01356 (6)0.00555 (6)
O(4)0.02317 (7)0.01860 (5)0.01627 (6)0.00354 (5)0.01083 (5)0.00651 (5)
C(1)0.01119 (4)0.01108 (3)0.00970 (4)0.00077 (3)0.00339 (3)0.00093 (3)
C(2)0.01507 (5)0.01562 (4)0.01093 (5)0.00115 (4)0.00496 (4)0.00207 (3)
C(3)0.01500 (5)0.02008 (5)0.01155 (5)0.00124 (4)0.00617 (4)0.00027 (4)
C(4)0.01428 (5)0.01830 (5)0.01418 (5)0.00077 (4)0.00705 (4)0.00097 (4)
C(5)0.01305 (4)0.01357 (4)0.01374 (5)0.00170 (3)0.00590 (4)0.00054 (3)
C(6)0.01067 (4)0.01085 (3)0.01042 (4)0.00028 (3)0.00399 (3)0.00078 (3)
C(7)0.01184 (4)0.01060 (3)0.01063 (4)0.00094 (3)0.00431 (3)0.00171 (3)
C(8)0.01086 (4)0.01102 (3)0.00964 (4)0.00054 (3)0.00363 (3)0.00090 (3)
C(9)0.01129 (4)0.01056 (3)0.01060 (4)0.00117 (3)0.00304 (3)0.00062 (3)
C(10)0.01415 (4)0.01501 (4)0.01128 (4)0.00100 (3)0.00576 (4)0.00172 (3)
H(3A)0.0315280.0297380.0276460.0065250.014820.008194
H(2)0.0378450.0280090.0280270.0116560.0131960.005116
H(3)0.0386690.0429880.0272740.0060830.0213610.001527
H(4)0.0351280.0368470.0364770.0002790.0209540.011332
H(5)0.035370.0253630.0312540.0084690.0134880.010856
H(7)0.0334690.0227410.0272660.0107160.0119660.007944
Geometric parameters (Å, º) top
O(1)—C(1)1.3729 (2)C(3)—H(3)1.0800
O(1)—C(9)1.3515 (2)C(4)—C(5)1.3853 (2)
O(2)—C(9)1.2263 (2)C(4)—H(4)1.0800
O(3)—C(10)1.3302 (2)C(5)—C(6)1.4071 (2)
O(3)—H(3A)1.0100C(5)—H(5)1.0800
O(4)—C(10)1.2142 (2)C(6)—C(7)1.4292 (2)
C(1)—C(2)1.3910 (2)C(7)—C(8)1.3591 (2)
C(1)—C(6)1.3998 (2)C(7)—H(7)1.0800
C(2)—C(3)1.3921 (2)C(8)—C(9)1.4559 (2)
C(2)—H(2)1.0800C(8)—C(10)1.4950 (2)
C(3)—C(4)1.4038 (2)
C(1)—O(1)—C(9)121.77 (1)C(6)—C(5)—H(5)118.94
C(10)—O(3)—H(3A)106.22C(1)—C(6)—C(5)118.72 (1)
O(1)—C(1)—C(2)117.13 (1)C(1)—C(6)—C(7)118.23 (1)
O(1)—C(1)—C(6)120.89 (1)C(5)—C(6)—C(7)123.03 (1)
C(2)—C(1)—C(6)121.99 (1)C(6)—C(7)—C(8)120.38 (1)
C(1)—C(2)—C(3)118.18 (1)C(6)—C(7)—H(7)118.98
C(1)—C(2)—H(2)121.58C(8)—C(7)—H(7)120.60
C(3)—C(2)—H(2)120.23C(7)—C(8)—C(9)119.77 (1)
C(2)—C(3)—C(4)121.12 (1)C(7)—C(8)—C(10)120.12 (1)
C(2)—C(3)—H(3)118.41C(9)—C(8)—C(10)120.11 (1)
C(4)—C(3)—H(3)120.47O(1)—C(9)—O(2)116.73 (1)
C(3)—C(4)—C(5)119.88 (1)O(1)—C(9)—C(8)118.81 (1)
C(3)—C(4)—H(4)121.35O(2)—C(9)—C(8)124.44 (1)
C(5)—C(4)—H(4)118.77O(3)—C(10)—O(4)120.85 (2)
C(4)—C(5)—C(6)120.10 (1)O(3)—C(10)—C(8)116.85 (1)
C(4)—C(5)—H(5)120.95O(4)—C(10)—C(8)122.29 (1)
C(1)—O(1)—C(9)—O(2)177.83 (2)H(3)—C(3)—C(4)—H(4)0.84
C(9)—O(1)—C(1)—C(2)175.56 (2)C(3)—C(4)—C(5)—C(6)0.08 (1)
C(9)—O(1)—C(1)—C(6)4.49 (1)C(3)—C(4)—C(5)—H(5)179.41
C(1)—O(1)—C(9)—C(8)3.66 (1)H(4)—C(4)—C(5)—C(6)179.11
H(3A)—O(2)—C(9)—O(1)176.76H(4)—C(4)—C(5)—H(5)0.22
C(9)—O(2)—H(3A)—O(3)12.53C(4)—C(5)—C(6)—C(1)0.61 (1)
H(3A)—O(2)—C(9)—C(8)4.82C(4)—C(5)—C(6)—C(7)177.96 (2)
C(10)—O(3)—H(3A)—O(2)8.67H(5)—C(5)—C(6)—C(1)179.95
H(3A)—O(3)—C(10)—O(4)178.28H(5)—C(5)—C(6)—C(7)1.39
H(3A)—O(3)—C(10)—C(8)1.35C(1)—C(6)—C(7)—C(8)0.73 (1)
O(1)—C(1)—C(2)—C(3)179.54 (2)C(1)—C(6)—C(7)—H(7)176.92
O(1)—C(1)—C(2)—H(2)1.43C(5)—C(6)—C(7)—C(8)177.84 (2)
O(1)—C(1)—C(6)—C(5)179.16 (2)C(5)—C(6)—C(7)—H(7)4.51
O(1)—C(1)—C(6)—C(7)2.20 (1)C(6)—C(7)—C(8)—C(9)1.47 (1)
C(6)—C(1)—C(2)—C(3)0.42 (1)C(6)—C(7)—C(8)—C(10)178.39 (2)
C(2)—C(1)—C(6)—C(5)0.79 (1)H(7)—C(7)—C(8)—C(9)176.14
C(2)—C(1)—C(6)—C(7)177.84 (2)H(7)—C(7)—C(8)—C(10)4.00
C(6)—C(1)—C(2)—H(2)178.62C(7)—C(8)—C(9)—O(1)0.67 (1)
C(1)—C(2)—C(3)—C(4)0.14 (1)C(7)—C(8)—C(9)—O(2)179.05 (2)
C(1)—C(2)—C(3)—H(3)179.82C(7)—C(8)—C(10)—O(3)176.21 (2)
H(2)—C(2)—C(3)—C(4)179.18C(7)—C(8)—C(10)—O(4)4.16 (2)
H(2)—C(2)—C(3)—H(3)1.13C(10)—C(8)—C(9)—O(1)179.47 (2)
C(2)—C(3)—C(4)—C(5)0.30 (1)C(10)—C(8)—C(9)—O(2)1.09 (1)
C(2)—C(3)—C(4)—H(4)179.48C(9)—C(8)—C(10)—O(3)3.65 (2)
H(3)—C(3)—C(4)—C(5)179.98C(9)—C(8)—C(10)—O(4)175.98 (2)

Experimental details

(1a)(2a)
Crystal data
Chemical formulaC9H8O2C10H6O4
Mr148.15190.15
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)100100
a, b, c (Å)5.5504 (1), 17.5427 (1), 7.7161 (1)11.1992 (1), 5.4662 (1), 13.7267 (2)
β (°) 96.296 (1) 107.256 (1)
V3)746.78 (2)802.49 (2)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.090.12
Crystal size (mm)0.57 × 0.36 × 0.100.60 × 0.52 × 0.29
Data collection
DiffractometerGoniometer Xcalibur, detector: Atlas (Gemini ultra Mo)
diffractometer
Goniometer Xcalibur, detector: Atlas (Gemini ultra Mo)
diffractometer
Absorption correctionMulti-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET) (compiled Apr 18 2008,18:17:43) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.18 (release 23-07-2008 CrysAlis171 .NET) (compiled Jul 23 2008,18:57:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Tmin, Tmax0.911, 0.9900.891, 0.965
No. of measured, independent and
observed [I > 3 σ(I)] reflections
70528, 6591, 4859 147662, 11309, 8933
Rint0.0230.023
(sin θ/λ)max1)1.0201.190
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.018, 0.014, 1.74 0.016, 0.014, 1.67
No. of reflections48598933
No. of parameters295367
H-atom treatmentOnly H-atom displacement parameters refined?
Δρmax, Δρmin (e Å3)0.13, 0.130.15, 0.14

Computer programs: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET) (compiled Apr 18 2008,18:17:43), SHELXS97 (Sheldrick, 1990), SHELXS97 (Sheldrick, 1998), Volkov et al., (2006).

Selected geometric parameters (Å, º) for (1a) top
O(1)—C(9)1.3087 (4)C(4)—C(5)1.3926 (4)
O(2)—C(9)1.2447 (4)C(5)—C(6)1.4024 (3)
C(1)—C(2)1.3911 (3)C(6)—C(7)1.4630 (3)
C(1)—C(6)1.4038 (3)C(7)—C(8)1.3446 (3)
C(2)—C(3)1.3943 (4)C(8)—C(9)1.4690 (3)
C(3)—C(4)1.3946 (4)
C(2)—C(1)—C(6)120.44 (2)C(5)—C(6)—C(7)118.97 (2)
C(1)—C(2)—C(3)120.43 (3)C(6)—C(7)—C(8)126.05 (2)
C(2)—C(3)—C(4)119.66 (3)C(7)—C(8)—C(9)122.16 (2)
C(3)—C(4)—C(5)120.01 (2)O(1)—C(9)—O(2)123.32 (3)
C(4)—C(5)—C(6)120.81 (2)O(1)—C(9)—C(8)116.54 (3)
C(1)—C(6)—C(5)118.64 (2)O(2)—C(9)—C(8)120.15 (2)
C(1)—C(6)—C(7)122.39 (2)
H(1A)—O(1)—C(9)—O(2)2.92C(3)—C(4)—C(5)—H(5)178.93
H(1A)—O(1)—C(9)—C(8)177.31H(4)—C(4)—C(5)—C(6)179.95
C(6)—C(1)—C(2)—C(3)0.05 (3)H(4)—C(4)—C(5)—H(5)0.74
C(2)—C(1)—C(6)—C(5)0.20 (2)C(4)—C(5)—C(6)—C(1)0.09 (2)
C(2)—C(1)—C(6)—C(7)179.85 (4)C(4)—C(5)—C(6)—C(7)179.75 (4)
C(6)—C(1)—C(2)—H(2)179.82H(5)—C(5)—C(6)—C(1)179.28
H(1)—C(1)—C(2)—C(3)177.72H(5)—C(5)—C(6)—C(7)1.06
H(1)—C(1)—C(2)—H(2)2.05C(1)—C(6)—C(7)—C(8)4.06 (2)
H(1)—C(1)—C(6)—C(5)177.99C(1)—C(6)—C(7)—H(7)177.03
H(1)—C(1)—C(6)—C(7)2.36C(5)—C(6)—C(7)—C(8)175.58 (4)
C(1)—C(2)—C(3)—C(4)0.43 (3)C(5)—C(6)—C(7)—H(7)3.32
C(1)—C(2)—C(3)—H(3)179.84C(6)—C(7)—C(8)—C(9)179.17 (4)
H(2)—C(2)—C(3)—C(4)179.81C(6)—C(7)—C(8)—H(8)0.02
H(2)—C(2)—C(3)—H(3)0.07H(7)—C(7)—C(8)—C(9)0.32
C(2)—C(3)—C(4)—C(5)0.54 (3)H(7)—C(7)—C(8)—H(8)178.87
C(2)—C(3)—C(4)—H(4)179.80C(7)—C(8)—C(9)—O(1)2.88 (3)
H(3)—C(3)—C(4)—C(5)179.72C(7)—C(8)—C(9)—O(2)176.90 (4)
H(3)—C(3)—C(4)—H(4)0.06H(8)—C(8)—C(9)—O(1)177.91
C(3)—C(4)—C(5)—C(6)0.28 (3)H(8)—C(8)—C(9)—O(2)2.31
Selected geometric parameters (Å, º) for (2a) top
O(1)—C(1)1.3729 (2)C(3)—C(4)1.4038 (2)
O(1)—C(9)1.3515 (2)C(4)—C(5)1.3853 (2)
O(2)—C(9)1.2263 (2)C(5)—C(6)1.4071 (2)
O(3)—C(10)1.3302 (2)C(6)—C(7)1.4292 (2)
O(4)—C(10)1.2142 (2)C(7)—C(8)1.3591 (2)
C(1)—C(2)1.3910 (2)C(8)—C(9)1.4559 (2)
C(1)—C(6)1.3998 (2)C(8)—C(10)1.4950 (2)
C(2)—C(3)1.3921 (2)
C(1)—O(1)—C(9)121.77 (1)C(6)—C(7)—C(8)120.38 (1)
O(1)—C(1)—C(2)117.13 (1)C(7)—C(8)—C(9)119.77 (1)
O(1)—C(1)—C(6)120.89 (1)C(7)—C(8)—C(10)120.12 (1)
C(2)—C(1)—C(6)121.99 (1)C(9)—C(8)—C(10)120.11 (1)
C(1)—C(2)—C(3)118.18 (1)O(1)—C(9)—O(2)116.73 (1)
C(2)—C(3)—C(4)121.12 (1)O(1)—C(9)—C(8)118.81 (1)
C(3)—C(4)—C(5)119.88 (1)O(2)—C(9)—C(8)124.44 (1)
C(4)—C(5)—C(6)120.10 (1)O(3)—C(10)—O(4)120.85 (2)
C(1)—C(6)—C(5)118.72 (1)O(3)—C(10)—C(8)116.85 (1)
C(1)—C(6)—C(7)118.23 (1)O(4)—C(10)—C(8)122.29 (1)
C(5)—C(6)—C(7)123.03 (1)
C(1)—O(1)—C(9)—O(2)177.83 (2)H(3)—C(3)—C(4)—H(4)0.84
C(9)—O(1)—C(1)—C(2)175.56 (2)C(3)—C(4)—C(5)—C(6)0.08 (1)
C(9)—O(1)—C(1)—C(6)4.49 (1)C(3)—C(4)—C(5)—H(5)179.41
C(1)—O(1)—C(9)—C(8)3.66 (1)H(4)—C(4)—C(5)—C(6)179.11
H(3A)—O(2)—C(9)—O(1)176.76H(4)—C(4)—C(5)—H(5)0.22
C(9)—O(2)—H(3A)—O(3)12.53C(4)—C(5)—C(6)—C(1)0.61 (1)
H(3A)—O(2)—C(9)—C(8)4.82C(4)—C(5)—C(6)—C(7)177.96 (2)
C(10)—O(3)—H(3A)—O(2)8.67H(5)—C(5)—C(6)—C(1)179.95
H(3A)—O(3)—C(10)—O(4)178.28H(5)—C(5)—C(6)—C(7)1.39
H(3A)—O(3)—C(10)—C(8)1.35C(1)—C(6)—C(7)—C(8)0.73 (1)
O(1)—C(1)—C(2)—C(3)179.54 (2)C(1)—C(6)—C(7)—H(7)176.92
O(1)—C(1)—C(2)—H(2)1.43C(5)—C(6)—C(7)—C(8)177.84 (2)
O(1)—C(1)—C(6)—C(5)179.16 (2)C(5)—C(6)—C(7)—H(7)4.51
O(1)—C(1)—C(6)—C(7)2.20 (1)C(6)—C(7)—C(8)—C(9)1.47 (1)
C(6)—C(1)—C(2)—C(3)0.42 (1)C(6)—C(7)—C(8)—C(10)178.39 (2)
C(2)—C(1)—C(6)—C(5)0.79 (1)H(7)—C(7)—C(8)—C(9)176.14
C(2)—C(1)—C(6)—C(7)177.84 (2)H(7)—C(7)—C(8)—C(10)4.00
C(6)—C(1)—C(2)—H(2)178.62C(7)—C(8)—C(9)—O(1)0.67 (1)
C(1)—C(2)—C(3)—C(4)0.14 (1)C(7)—C(8)—C(9)—O(2)179.05 (2)
C(1)—C(2)—C(3)—H(3)179.82C(7)—C(8)—C(10)—O(3)176.21 (2)
H(2)—C(2)—C(3)—C(4)179.18C(7)—C(8)—C(10)—O(4)4.16 (2)
H(2)—C(2)—C(3)—H(3)1.13C(10)—C(8)—C(9)—O(1)179.47 (2)
C(2)—C(3)—C(4)—C(5)0.30 (1)C(10)—C(8)—C(9)—O(2)1.09 (1)
C(2)—C(3)—C(4)—H(4)179.48C(9)—C(8)—C(10)—O(3)3.65 (2)
H(3)—C(3)—C(4)—C(5)179.98C(9)—C(8)—C(10)—O(4)175.98 (2)
 

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