A new polymorph of ortho-ethoxy-trans-cinnamic acid: single-to-single-crystal phase transformation and mechanism

The α-polymorph of ortho-ethoxy-trans-cinnamic acid (OETCA) undergoes a reversible single-crystal-to-single-crystal phase transformation at 333 K. The new high-temperature polymorph (α′-OETCA) is stable between 333 and 393 K with three molecules in the asymmetric unit (Z′ = 3), space group P. Unlike the other polymorphs (and solvate) of OETCA recently reported, two of the molecules in α′-OETCA deviate significantly from planarity. This conformational change results in the corrugated sheet-type structure of α′-OETCA. The sheets are made up of ribbons, each composed of hydrogen-bonded pairs (via the —COOH groups), which are further connected by CH...O interactions. When exposed to UV radiation the α′-OETCA polymorph can be stabilized below 333 K with ca 8% of the monomer converted into the photodimer. The crystal structures of α′-OETCA are reported at two temperatures above the phase transition point (at 345 and 375 K) as well as the stabilized forms at 173 and 293 K. A mechanism for the phase transition involving a cooperative conformational transformation coupled with a shift of layers of OETCA molecules is proposed. The α′-OETCA polymorph is also an example of a cinnamic acid derivative where two different potentially photoreactive environments exist in one crystal in which each unit cell has two non-centrosymmetric predimer sites and one centrosymmetric predimer site.

Computing details

For all compounds, data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT+(Bruker, 1999a); data reduction: SAINT+(Bruker, 1999a); program(s) used to solve structure: SHELXTL (Bruker, 1999b); program(s) used to refine structure: SHELXTL (Bruker, 1999b); molecular graphics: PLATON (Spek, 2003), SHELXTL (Bruker, 1999b), SCHAKAL97 (Keller, 1997) and DS ViewerPro (Accelrys, 2002); software used to prepare material for publication: SHELXTL (Bruker, 1999b).

Figures

(almer60) (E)-3-(2-Ethoxyphenyl)propenoic acid

Crystal data

C11H12O3	Z = 6
Mr = 192.21	F(000) = 612
Triclinic, P1	Dx = 1.231 Mg m^−3
Hall symbol: -P 1	Melting point: 134 - 135 °C K
a = 8.7336 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9590 (7) Å	Cell parameters from 665 reflections
c = 17.2709 (10) Å	θ = 2.7–21.6°
α = 91.232 (4)°	µ = 0.09 mm^−1
β = 92.703 (4)°	T = 345 K
γ = 109.472 (4)°	Prismic, colourless
V = 1555.53 (15) Å^3	1.00 × 0.34 × 0.31 mm

Data collection

Bruker SMART 1K diffractometer	2689 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 1.2°
phi and ω scans	h = −10→10
4937 measured reflections	k = −12→12
4937 independent reflections	l = 0→20

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.152	w = 1/[σ^2(Fo^2) + (0.0807P)^2 + 0.0096P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4937 reflections	Δρmax = 0.16 e Å^−3
386 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0085 (17)

Special details

Experimental. The following alerts are triggered when using the ACTA-C CIF validation software.

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ······. 0.90 PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size ······. 1.00 mm REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 4937 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5485 Completeness (_total/calc) 90.01% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ···. 0.90 —————- Author response: These issues are addressed in the paper associated with this structure: "Two crystals with different orientations were used (size: 1.0 x 0.34 x 0.33 and 1.0 x 0.34 x 0.28 mm respectively; collimator size: 0.8 mm) and a data set at each temperature was collected for each crystal. Large crystals were used to counteract the affect of sublimation at 375 K by allowing quick data collection times (about 1.5 h); smaller crystals were found to have almost disappeared by the time the data collection run was over; alternative methods of preventing sublimation such as coating the crystals with epoxy glue (Hashizume et al., 2003) or sealing in capillaries (Botoshansky et al., 1998) were avoided as it was thought that they might interfere with the phase transition. Two crystals in two different orientations were necessary as the heating device physically restricted the amount of data collected on each crystal to about 60% completeness to 25 ° Theta, for a triclinic unit cell, while collecting two data sets on two crystals mounted in different orientations ensured a data completeness of about 90% to 25 ° theta." See article for further details

PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) H1C PLAT355_ALERT_3_A Long O—H Bond (0.82 A) O11B - H1B ··· 1.24 A ng. PLAT355_ALERT_3_A Long O—H Bond (0.82 A) O12A - H1A ··· 1.17 A ng. PLAT417_ALERT_2_B Short Inter D—H.·H—D H1A.. H1A.. 1.95 A ng. PLAT420_ALERT_2_B D—H Without Acceptor O11B - H1B ··· ? PLAT430_ALERT_2_B Short Inter D···A Contact O11C.. O12B.. 2.64 A ng. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ ···. ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ···. ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ············ 0.33 Ratio ——— Author response: From article associated with this structure: >From article "··· the hydrogen bond data was obtained by locating the carboxylic hydrogen atom positions in the difference map and then fixing them to their parent atom. In contrast to the usual O—H bond length of about 0.82 Å (the default for SHELX at 345 K), O—H lengths in the a' polymorph at 345/375 K are on average about 1.21/1.28 Å long or about 46/48% of the O···O distance (average 2.63/2.64 Å) respectively i.e. they are almost in the middle of the hydrogen bond being shared almost equally between two carboxylic oxygen atoms." We chose to use located positions for the carboxylic H atoms, rather than fix them using AFIX in SHELX, as this may more accurately describe the hydrogen bonding situation. The located hydrogen atoms being in the middle of the carboxylic acid bond does cause some problems with platons builtin CIF check criteria, which is not able to correctly connect the molecules leading to other errors related to an incorrect calculation of the number of molecules in the unit cell.

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
C1A	1.0179 (3)	0.0351 (2)	0.22241 (13)	0.0789 (6)
C2A	1.0129 (3)	0.0300 (2)	0.30283 (13)	0.0813 (6)
C3A	1.1498 (3)	0.0399 (3)	0.34824 (15)	0.1015 (8)
H3A	1.1450	0.0370	0.4019	0.122*
C4A	1.2939 (3)	0.0541 (3)	0.31491 (19)	0.1150 (9)
H4A	1.3863	0.0606	0.3461	0.138*
C5A	1.3024 (3)	0.0586 (3)	0.2361 (2)	0.1148 (9)
H5A	1.4000	0.0675	0.2136	0.138*
C6A	1.1666 (3)	0.0502 (2)	0.19071 (16)	0.1007 (8)
H6A	1.1737	0.0546	0.1372	0.121*
C11A	0.8700 (3)	0.0252 (2)	0.17502 (13)	0.0836 (7)
H11A	0.7784	0.0199	0.2019	0.100*
C12A	0.8519 (3)	0.0230 (2)	0.09937 (14)	0.0918 (7)
H12A	0.9419	0.0294	0.0709	0.110*
C13A	0.6983 (3)	0.0109 (2)	0.05687 (15)	0.0866 (7)
C21A	0.8489 (3)	0.0112 (3)	0.41270 (13)	0.1027 (8)
H21E	0.9250	0.0890	0.4381	0.123*
H21F	0.8722	−0.0631	0.4328	0.123*
C22A	0.6795 (3)	0.0018 (3)	0.42765 (15)	0.1280 (10)
H22G	0.6576	0.0757	0.4075	0.192*
H22H	0.6660	−0.0005	0.4825	0.192*
H22I	0.6052	−0.0758	0.4026	0.192*
O11A	0.6952 (2)	0.01020 (17)	−0.01537 (9)	0.1090 (6)
O12A	0.5726 (2)	0.00053 (17)	0.09525 (8)	0.1068 (6)
H1A	0.4692	0.0100	0.0526	0.242 (19)*
O21A	0.86409 (18)	0.01490 (16)	0.33134 (8)	0.0961 (5)
C1B	0.8074 (2)	0.3527 (2)	0.13506 (12)	0.0718 (6)
C2B	0.8054 (2)	0.3390 (2)	0.05442 (12)	0.0726 (6)
C3B	0.6699 (3)	0.3333 (2)	0.00898 (14)	0.0944 (7)
H3B	0.6701	0.3246	−0.0447	0.113*
C4B	0.5329 (3)	0.3405 (3)	0.04312 (17)	0.1079 (9)
H4B	0.4408	0.3357	0.0122	0.129*
C5B	0.5317 (3)	0.3547 (3)	0.12155 (18)	0.1101 (9)
H5B	0.4397	0.3604	0.1442	0.132*
C6B	0.6668 (3)	0.3604 (2)	0.16679 (15)	0.0947 (7)
H6B	0.6650	0.3697	0.2203	0.114*
C11B	0.9519 (3)	0.35932 (19)	0.18293 (12)	0.0738 (6)
H11B	1.0441	0.3651	0.1564	0.089*
C12B	0.9684 (3)	0.3582 (2)	0.25900 (12)	0.0845 (7)
H12B	0.8783	0.3531	0.2870	0.101*
C13B	1.1174 (3)	0.3643 (2)	0.30209 (12)	0.0803 (6)
C21B	0.9511 (2)	0.3152 (2)	−0.05662 (11)	0.0817 (6)
H21A	0.9373	0.3885	−0.0828	0.098*
H21B	0.8650	0.2372	−0.0758	0.098*
C22B	1.1141 (3)	0.3047 (2)	−0.07109 (13)	0.0971 (8)
H22D	1.1979	0.3837	−0.0538	0.146*
H22E	1.1208	0.2896	−0.1256	0.146*
H22F	1.1279	0.2339	−0.0432	0.146*
O11B	1.1114 (2)	0.34873 (16)	0.37454 (8)	0.0982 (5)
H1B	1.2335	0.3478	0.4136	0.251 (18)*
O12B	1.24646 (19)	0.38378 (16)	0.26678 (8)	0.0981 (5)
O21B	0.94565 (16)	0.33197 (15)	0.02525 (7)	0.0825 (5)
C1C	0.2044 (2)	0.6761 (2)	0.41880 (12)	0.0727 (6)
C2C	0.2171 (2)	0.6971 (2)	0.33960 (12)	0.0746 (6)
C3C	0.0873 (3)	0.7034 (2)	0.29414 (14)	0.0952 (7)
H3C	0.0977	0.7173	0.2414	0.114*
C4C	−0.0581 (3)	0.6893 (3)	0.32632 (18)	0.1069 (8)
H4C	−0.1459	0.6934	0.2951	0.128*
C5C	−0.0750 (3)	0.6694 (2)	0.40403 (18)	0.1060 (9)
H5C	−0.1734	0.6606	0.4257	0.127*
C6C	0.0540 (3)	0.6626 (2)	0.44922 (14)	0.0922 (7)
H6C	0.0418	0.6485	0.5018	0.111*
C11C	0.3420 (3)	0.6665 (2)	0.46571 (12)	0.0773 (6)
H11C	0.4367	0.6781	0.4400	0.093*
C12C	0.3496 (3)	0.6434 (2)	0.54027 (13)	0.0857 (7)
H12C	0.2573	0.6318	0.5679	0.103*
C13C	0.4940 (3)	0.6350 (2)	0.58137 (13)	0.0854 (7)
C21C	0.3828 (3)	0.7136 (3)	0.23053 (12)	0.0958 (8)
H21C	0.3737	0.7938	0.2116	0.115*
H21D	0.2983	0.6417	0.2040	0.115*
C22C	0.5453 (3)	0.7060 (3)	0.21584 (13)	0.1112 (9)
H22A	0.6278	0.7765	0.2434	0.167*
H22B	0.5615	0.7114	0.1613	0.167*
H22C	0.5518	0.6253	0.2334	0.167*
O11C	0.4853 (2)	0.60726 (18)	0.65238 (9)	0.1148 (6)
H1C	0.6111	0.6123	0.6892	0.217 (14)*
O12C	0.62491 (19)	0.65652 (16)	0.54689 (8)	0.1010 (5)
O21C	0.36550 (16)	0.70875 (16)	0.31198 (8)	0.0909 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0921 (16)	0.0695 (17)	0.0742 (16)	0.0259 (13)	0.0064 (13)	0.0022 (12)
C2A	0.0849 (16)	0.0832 (18)	0.0775 (16)	0.0308 (13)	0.0027 (13)	0.0020 (12)
C3A	0.1018 (18)	0.121 (2)	0.0874 (17)	0.0475 (16)	−0.0076 (15)	−0.0018 (15)
C4A	0.0935 (19)	0.127 (3)	0.131 (3)	0.0472 (17)	−0.0027 (17)	−0.0030 (19)
C5A	0.096 (2)	0.118 (2)	0.134 (3)	0.0394 (17)	0.0254 (19)	0.0007 (19)
C6A	0.111 (2)	0.098 (2)	0.0949 (19)	0.0355 (16)	0.0203 (17)	0.0012 (14)
C11A	0.1156 (19)	0.0688 (17)	0.0641 (15)	0.0264 (14)	0.0138 (13)	0.0033 (12)
C12A	0.118 (2)	0.0861 (19)	0.0708 (16)	0.0311 (14)	0.0204 (14)	0.0061 (13)
C13A	0.1121 (19)	0.0744 (18)	0.0676 (16)	0.0236 (14)	0.0058 (15)	0.0047 (12)
C21A	0.1171 (19)	0.133 (2)	0.0630 (15)	0.0487 (17)	0.0043 (13)	0.0041 (14)
C22A	0.110 (2)	0.180 (3)	0.097 (2)	0.052 (2)	0.0186 (16)	−0.0015 (19)
O11A	0.1298 (14)	0.1283 (16)	0.0600 (10)	0.0308 (11)	0.0107 (9)	0.0005 (9)
O12A	0.1314 (14)	0.1297 (16)	0.0580 (10)	0.0404 (11)	0.0129 (10)	0.0105 (9)
O21A	0.0907 (11)	0.1340 (15)	0.0635 (10)	0.0377 (10)	0.0006 (8)	0.0044 (9)
C1B	0.0784 (14)	0.0696 (16)	0.0700 (14)	0.0273 (11)	0.0074 (11)	0.0065 (11)
C2B	0.0721 (13)	0.0790 (17)	0.0686 (14)	0.0278 (12)	0.0027 (11)	0.0071 (11)
C3B	0.0820 (15)	0.117 (2)	0.0852 (17)	0.0354 (15)	−0.0035 (13)	0.0047 (14)
C4B	0.0764 (16)	0.131 (3)	0.118 (2)	0.0377 (15)	−0.0009 (15)	0.0089 (18)
C5B	0.0831 (18)	0.135 (3)	0.121 (2)	0.0448 (16)	0.0245 (17)	0.0127 (18)
C6B	0.0952 (17)	0.110 (2)	0.0860 (17)	0.0412 (15)	0.0218 (14)	0.0110 (13)
C11B	0.0903 (15)	0.0715 (16)	0.0603 (13)	0.0280 (12)	0.0053 (11)	0.0020 (11)
C12B	0.1016 (17)	0.0931 (19)	0.0617 (15)	0.0359 (14)	0.0113 (13)	0.0012 (12)
C13B	0.1071 (18)	0.0784 (18)	0.0566 (15)	0.0328 (14)	0.0034 (14)	0.0012 (11)
C21B	0.0888 (15)	0.0910 (19)	0.0603 (14)	0.0236 (13)	0.0019 (11)	0.0028 (11)
C22B	0.0970 (16)	0.115 (2)	0.0885 (17)	0.0465 (15)	0.0159 (13)	0.0014 (14)
O11B	0.1233 (13)	0.1266 (15)	0.0514 (9)	0.0503 (11)	0.0069 (8)	0.0034 (8)
O12B	0.1034 (12)	0.1256 (15)	0.0627 (10)	0.0333 (10)	0.0106 (9)	0.0158 (8)
O21B	0.0809 (9)	0.1130 (13)	0.0597 (9)	0.0413 (8)	0.0003 (7)	−0.0014 (8)
C1C	0.0783 (14)	0.0723 (16)	0.0676 (14)	0.0254 (12)	0.0050 (11)	0.0010 (11)
C2C	0.0722 (14)	0.0806 (17)	0.0706 (15)	0.0254 (12)	0.0037 (11)	−0.0003 (12)
C3C	0.0892 (16)	0.119 (2)	0.0835 (16)	0.0436 (15)	−0.0038 (14)	0.0060 (14)
C4C	0.0826 (17)	0.122 (2)	0.120 (2)	0.0399 (15)	−0.0032 (15)	0.0028 (18)
C5C	0.0841 (17)	0.110 (2)	0.131 (2)	0.0398 (15)	0.0251 (17)	0.0108 (18)
C6C	0.0953 (17)	0.094 (2)	0.0918 (17)	0.0351 (14)	0.0253 (15)	0.0093 (14)
C11C	0.0937 (15)	0.0762 (17)	0.0597 (14)	0.0242 (12)	0.0143 (12)	0.0013 (11)
C12C	0.0906 (16)	0.099 (2)	0.0670 (15)	0.0301 (14)	0.0104 (12)	0.0043 (13)
C13C	0.1011 (18)	0.0911 (19)	0.0574 (14)	0.0232 (14)	0.0057 (13)	0.0026 (12)
C21C	0.1013 (17)	0.130 (2)	0.0623 (15)	0.0452 (16)	0.0101 (12)	0.0192 (13)
C22C	0.0983 (17)	0.150 (3)	0.0949 (18)	0.0500 (17)	0.0255 (14)	0.0228 (16)
O11C	0.1112 (13)	0.1663 (18)	0.0591 (10)	0.0343 (11)	0.0077 (9)	0.0258 (10)
O12C	0.1043 (12)	0.1383 (16)	0.0638 (10)	0.0442 (11)	0.0106 (9)	0.0095 (9)
O21C	0.0812 (10)	0.1346 (14)	0.0594 (9)	0.0389 (9)	0.0046 (7)	0.0080 (8)

Geometric parameters (Å, º)

C1A—C2A	1.393 (3)	C11B—H11B	0.9300
C1A—C6A	1.394 (3)	C12B—C13B	1.449 (3)
C1A—C11A	1.467 (3)	C12B—H12B	0.9300
C2A—O21A	1.371 (2)	C13B—O12B	1.264 (2)
C2A—C3A	1.371 (3)	C13B—O11B	1.268 (2)
C3A—C4A	1.371 (3)	C21B—O21B	1.427 (2)
C3A—H3A	0.9300	C21B—C22B	1.498 (3)
C4A—C5A	1.367 (3)	C21B—H21A	0.9700
C4A—H4A	0.9300	C21B—H21B	0.9700
C5A—C6A	1.366 (3)	C22B—H22D	0.9600
C5A—H5A	0.9300	C22B—H22E	0.9600
C6A—H6A	0.9300	C22B—H22F	0.9600
C11A—C12A	1.307 (3)	O11B—H1B	1.2377
C11A—H11A	0.9300	C1C—C2C	1.395 (3)
C12A—C13A	1.463 (3)	C1C—C6C	1.400 (3)
C12A—H12A	0.9300	C1C—C11C	1.452 (3)
C13A—O11A	1.246 (2)	C2C—O21C	1.369 (2)
C13A—O12A	1.283 (2)	C2C—C3C	1.370 (3)
C21A—O21A	1.418 (2)	C3C—C4C	1.373 (3)
C21A—C22A	1.484 (3)	C3C—H3C	0.9300
C21A—H21E	0.9700	C4C—C5C	1.371 (3)
C21A—H21F	0.9700	C4C—H4C	0.9300
C22A—H22G	0.9600	C5C—C6C	1.364 (3)
C22A—H22H	0.9600	C5C—H5C	0.9300
C22A—H22I	0.9600	C6C—H6C	0.9300
O12A—H1A	1.1705	C11C—C12C	1.321 (3)
C1B—C6B	1.394 (3)	C11C—H11C	0.9300
C1B—C2B	1.396 (3)	C12C—C13C	1.448 (3)
C1B—C11B	1.456 (3)	C12C—H12C	0.9300
C2B—O21B	1.371 (2)	C13C—O12C	1.268 (2)
C2B—C3B	1.371 (3)	C13C—O11C	1.269 (2)
C3B—C4B	1.383 (3)	C21C—O21C	1.422 (2)
C3B—H3B	0.9300	C21C—C22C	1.482 (3)
C4B—C5B	1.361 (3)	C21C—H21C	0.9700
C4B—H4B	0.9300	C21C—H21D	0.9700
C5B—C6B	1.367 (3)	C22C—H22A	0.9600
C5B—H5B	0.9300	C22C—H22B	0.9600
C6B—H6B	0.9300	C22C—H22C	0.9600
C11B—C12B	1.316 (3)	O11C—H1C	1.2278
C2A—C1A—C6A	117.3 (2)	C11B—C12B—C13B	124.5 (2)
C2A—C1A—C11A	119.7 (2)	C11B—C12B—H12B	117.8
C6A—C1A—C11A	122.9 (2)	C13B—C12B—H12B	117.8
O21A—C2A—C3A	124.0 (2)	O12B—C13B—O11B	122.7 (2)
O21A—C2A—C1A	115.3 (2)	O12B—C13B—C12B	119.60 (19)
C3A—C2A—C1A	120.7 (2)	O11B—C13B—C12B	117.7 (2)
C2A—C3A—C4A	120.3 (2)	O21B—C21B—C22B	106.92 (16)
C2A—C3A—H3A	119.9	O21B—C21B—H21A	110.3
C4A—C3A—H3A	119.9	C22B—C21B—H21A	110.3
C5A—C4A—C3A	120.3 (3)	O21B—C21B—H21B	110.3
C5A—C4A—H4A	119.8	C22B—C21B—H21B	110.3
C3A—C4A—H4A	119.8	H21A—C21B—H21B	108.6
C6A—C5A—C4A	119.6 (2)	C21B—C22B—H22D	109.5
C6A—C5A—H5A	120.2	C21B—C22B—H22E	109.5
C4A—C5A—H5A	120.2	H22D—C22B—H22E	109.5
C5A—C6A—C1A	121.7 (2)	C21B—C22B—H22F	109.5
C5A—C6A—H6A	119.1	H22D—C22B—H22F	109.5
C1A—C6A—H6A	119.1	H22E—C22B—H22F	109.5
C12A—C11A—C1A	127.6 (2)	C13B—O11B—H1B	120.3
C12A—C11A—H11A	116.2	C2B—O21B—C21B	118.69 (15)
C1A—C11A—H11A	116.2	C2C—C1C—C6C	117.0 (2)
C11A—C12A—C13A	123.8 (2)	C2C—C1C—C11C	120.26 (18)
C11A—C12A—H12A	118.1	C6C—C1C—C11C	122.7 (2)
C13A—C12A—H12A	118.1	O21C—C2C—C3C	123.8 (2)
O11A—C13A—O12A	122.8 (2)	O21C—C2C—C1C	115.22 (19)
O11A—C13A—C12A	118.3 (2)	C3C—C2C—C1C	121.02 (19)
O12A—C13A—C12A	118.9 (2)	C2C—C3C—C4C	120.1 (2)
O21A—C21A—C22A	107.8 (2)	C2C—C3C—H3C	120.0
O21A—C21A—H21E	110.2	C4C—C3C—H3C	120.0
C22A—C21A—H21E	110.2	C5C—C4C—C3C	120.6 (2)
O21A—C21A—H21F	110.2	C5C—C4C—H4C	119.7
C22A—C21A—H21F	110.2	C3C—C4C—H4C	119.7
H21E—C21A—H21F	108.5	C6C—C5C—C4C	119.3 (2)
C21A—C22A—H22G	109.5	C6C—C5C—H5C	120.3
C21A—C22A—H22H	109.5	C4C—C5C—H5C	120.3
H22G—C22A—H22H	109.5	C5C—C6C—C1C	122.0 (2)
C21A—C22A—H22I	109.5	C5C—C6C—H6C	119.0
H22G—C22A—H22I	109.5	C1C—C6C—H6C	119.0
H22H—C22A—H22I	109.5	C12C—C11C—C1C	128.2 (2)
C13A—O12A—H1A	108.7	C12C—C11C—H11C	115.9
C2A—O21A—C21A	118.96 (18)	C1C—C11C—H11C	115.9
C6B—C1B—C2B	117.2 (2)	C11C—C12C—C13C	123.6 (2)
C6B—C1B—C11B	122.2 (2)	C11C—C12C—H12C	118.2
C2B—C1B—C11B	120.53 (18)	C13C—C12C—H12C	118.2
O21B—C2B—C3B	123.55 (19)	O12C—C13C—O11C	121.7 (2)
O21B—C2B—C1B	115.65 (18)	O12C—C13C—C12C	120.2 (2)
C3B—C2B—C1B	120.81 (19)	O11C—C13C—C12C	118.0 (2)
C2B—C3B—C4B	119.9 (2)	O21C—C21C—C22C	107.66 (17)
C2B—C3B—H3B	120.1	O21C—C21C—H21C	110.2
C4B—C3B—H3B	120.1	C22C—C21C—H21C	110.2
C5B—C4B—C3B	120.6 (2)	O21C—C21C—H21D	110.2
C5B—C4B—H4B	119.7	C22C—C21C—H21D	110.2
C3B—C4B—H4B	119.7	H21C—C21C—H21D	108.5
C4B—C5B—C6B	119.5 (2)	C21C—C22C—H22A	109.5
C4B—C5B—H5B	120.3	C21C—C22C—H22B	109.5
C6B—C5B—H5B	120.3	H22A—C22C—H22B	109.5
C5B—C6B—C1B	122.0 (2)	C21C—C22C—H22C	109.5
C5B—C6B—H6B	119.0	H22A—C22C—H22C	109.5
C1B—C6B—H6B	119.0	H22B—C22C—H22C	109.5
C12B—C11B—C1B	128.2 (2)	C13C—O11C—H1C	118.0
C12B—C11B—H11B	115.9	C2C—O21C—C21C	118.80 (16)
C1B—C11B—H11B	115.9
C6A—C1A—C2A—O21A	−179.91 (18)	C11B—C1B—C6B—C5B	179.7 (2)
C11A—C1A—C2A—O21A	0.3 (3)	C6B—C1B—C11B—C12B	8.3 (4)
C6A—C1A—C2A—C3A	0.2 (3)	C2B—C1B—C11B—C12B	−172.1 (2)
C11A—C1A—C2A—C3A	−179.6 (2)	C1B—C11B—C12B—C13B	179.6 (2)
O21A—C2A—C3A—C4A	179.6 (2)	C11B—C12B—C13B—O12B	6.8 (3)
C1A—C2A—C3A—C4A	−0.5 (4)	C11B—C12B—C13B—O11B	−172.8 (2)
C2A—C3A—C4A—C5A	0.1 (4)	C3B—C2B—O21B—C21B	−1.3 (3)
C3A—C4A—C5A—C6A	0.6 (4)	C1B—C2B—O21B—C21B	178.70 (17)
C4A—C5A—C6A—C1A	−0.9 (4)	C22B—C21B—O21B—C2B	−177.41 (17)
C2A—C1A—C6A—C5A	0.5 (4)	C6C—C1C—C2C—O21C	−179.48 (17)
C11A—C1A—C6A—C5A	−179.7 (2)	C11C—C1C—C2C—O21C	−0.7 (3)
C2A—C1A—C11A—C12A	−177.0 (2)	C6C—C1C—C2C—C3C	−0.3 (3)
C6A—C1A—C11A—C12A	3.2 (4)	C11C—C1C—C2C—C3C	178.5 (2)
C1A—C11A—C12A—C13A	179.1 (2)	O21C—C2C—C3C—C4C	179.3 (2)
C11A—C12A—C13A—O11A	179.8 (2)	C1C—C2C—C3C—C4C	0.2 (4)
C11A—C12A—C13A—O12A	−0.7 (4)	C2C—C3C—C4C—C5C	0.3 (4)
C3A—C2A—O21A—C21A	1.1 (3)	C3C—C4C—C5C—C6C	−0.5 (4)
C1A—C2A—O21A—C21A	−178.81 (19)	C4C—C5C—C6C—C1C	0.4 (4)
C22A—C21A—O21A—C2A	176.8 (2)	C2C—C1C—C6C—C5C	0.0 (3)
C6B—C1B—C2B—O21B	179.90 (18)	C11C—C1C—C6C—C5C	−178.7 (2)
C11B—C1B—C2B—O21B	0.3 (3)	C2C—C1C—C11C—C12C	−177.9 (2)
C6B—C1B—C2B—C3B	−0.1 (3)	C6C—C1C—C11C—C12C	0.8 (4)
C11B—C1B—C2B—C3B	−179.7 (2)	C1C—C11C—C12C—C13C	179.6 (2)
O21B—C2B—C3B—C4B	179.7 (2)	C11C—C12C—C13C—O12C	3.6 (4)
C1B—C2B—C3B—C4B	−0.3 (3)	C11C—C12C—C13C—O11C	−177.3 (2)
C2B—C3B—C4B—C5B	0.7 (4)	C3C—C2C—O21C—C21C	−7.1 (3)
C3B—C4B—C5B—C6B	−0.7 (4)	C1C—C2C—O21C—C21C	172.03 (18)
C4B—C5B—C6B—C1B	0.3 (4)	C22C—C21C—O21C—C2C	−171.53 (19)
C2B—C1B—C6B—C5B	0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11C—H1C···O12B^i	1.23	1.41	2.642 (2)	178
O11B—H1B···O12C^i	1.24	1.40	2.635 (2)	176
O12A—H1A···O11A^ii	1.17	1.49	2.626 (3)	161

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

(almer80) (E)-3-(2-Ethoxyphenyl)propenoic acid

Crystal data

C11H12O3	Z = 6
Mr = 192.21	F(000) = 612
Triclinic, P1	Dx = 1.218 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7373 (5) Å	Cell parameters from 797 reflections
b = 11.0167 (8) Å	θ = 2.3–20.9°
c = 17.295 (1) Å	µ = 0.09 mm^−1
α = 91.187 (4)°	T = 375 K
β = 92.775 (5)°	Prismic, colourless
γ = 108.938 (4)°	1.00 × 0.34 × 0.31 mm
V = 1571.62 (17) Å^3

Data collection

Bruker SMART 1K diffractometer	1906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 1.2°
phi and ω scans	h = −10→10
4947 measured reflections	k = −12→12
4947 independent reflections	l = 0→20

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.0788P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.88	(Δ/σ)max < 0.001
4947 reflections	Δρmax = 0.15 e Å^−3
386 parameters	Δρmin = −0.11 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0062 (13)

Special details

Experimental. The following alerts are triggered when using the ACTA-C CIF validation software.

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ······. 0.89 REFLT03_ALERT_3_B Reflection count < 90% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 4947 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5534 Completeness (_total/calc) 89.39% PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ···. 0.89 PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ···. 39 Perc. PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size ······. 1.00 mm ———- Author response: These issues are addressed in the paper associated with this structure: "Two crystals with different orientations were used (size: 1.0 x 0.34 x 0.33 and 1.0 x 0.34 x 0.28 mm respectively; collimator size: 0.8 mm) and a data set at each temperature was collected for each crystal. Large crystals were used to counteract the affect of sublimation at 375 K by allowing quick data collection times (about 1.5 h); smaller crystals were found to have almost disappeared by the time the data collection run was over; alternative methods of preventing sublimation such as coating the crystals with epoxy glue (Hashizume et al., 2003) or sealing in capillaries (Botoshansky et al., 1998) were avoided as it was thought that they might interfere with the phase transition. Two crystals in two different orientations were necessary as the heating device physically restricted the amount of data collected on each crystal to about 60% completeness to 25 ° Theta, for a triclinic unit cell, while collecting two data sets on two crystals mounted in different orientations ensured a data completeness of about 90% to 25 ° theta." See article for further details

PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) H1C PLAT355_ALERT_3_A Long O—H Bond (0.82 A) O12B - H1B ··· 1.31 A ng. PLAT355_ALERT_3_A Long O—H Bond (0.82 A) O12A - H1A ··· 1.26 A ng. PLAT772_ALERT_2_A Suspect O—H Bond in CIF: O12B –H1B.. 1.31 A ng. PLAT420_ALERT_2_B D—H Without Acceptor O12A - H1A ··· ? PLAT420_ALERT_2_B D—H Without Acceptor O12B - H1B ··· ? PLAT430_ALERT_2_B Short Inter D···A Contact O11B.. O12C.. 2.64 A ng. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ ···. ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ···. ? ——— Author response: From article associated with this structure: >From article "··· the hydrogen bond data was obtained by locating the carboxylic hydrogen atom positions in the difference map and then fixing them to their parent atom. In contrast to the usual O—H bond length of about 0.82 Å (the default for SHELX at 345 K), O—H lengths in the a' polymorph at 345/375 K are on average about 1.21/1.28 Å long or about 46/48% of the O···O distance (average 2.63/2.64 Å) respectively i.e. they are almost in the middle of the hydrogen bond being shared almost equally between two carboxylic oxygen atoms." We chose to use located positions for the carboxylic H atoms, rather than fix them using AFIX in SHELX, as this may more accurately describe the hydrogen bonding situation. The located hydrogen atoms being in the middle of the carboxylic acid bond does cause some problems with platons builtin CIF check criteria, which is not able to correctly connect the molecules leading to other errors related to an incorrect calculation of the number of molecules in the unit cell.

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
C1A	1.0173 (4)	0.0345 (3)	0.22231 (19)	0.0918 (8)
C2A	1.0123 (4)	0.0293 (3)	0.30236 (19)	0.0950 (9)
C3A	1.1485 (5)	0.0389 (3)	0.34807 (19)	0.1192 (11)
H3A	1.1434	0.0352	0.4016	0.143*
C4A	1.2923 (5)	0.0541 (3)	0.3147 (3)	0.1342 (13)
H4A	1.3845	0.0606	0.3459	0.161*
C5A	1.3023 (5)	0.0598 (3)	0.2362 (3)	0.1317 (13)
H5A	1.4004	0.0705	0.2140	0.158*
C6A	1.1658 (5)	0.0497 (3)	0.1908 (2)	0.1167 (11)
H6A	1.1724	0.0530	0.1373	0.140*
C11A	0.8693 (4)	0.0251 (3)	0.17491 (18)	0.0988 (10)
H11A	0.7778	0.0199	0.2017	0.119*
C12A	0.8523 (5)	0.0233 (3)	0.1006 (2)	0.1088 (10)
H12A	0.9425	0.0304	0.0723	0.131*
C13A	0.6961 (5)	0.0104 (3)	0.0575 (2)	0.1000 (10)
C21A	0.8482 (4)	0.0113 (3)	0.41231 (17)	0.1272 (11)
H21E	0.9225	0.0890	0.4375	0.153*
H21F	0.8736	−0.0617	0.4328	0.153*
C22A	0.6799 (4)	0.0007 (4)	0.42699 (18)	0.1505 (14)
H22G	0.6552	0.0724	0.4056	0.226*
H22H	0.6671	0.0004	0.4818	0.226*
H22I	0.6075	−0.0777	0.4031	0.226*
O11A	0.6956 (3)	0.0099 (2)	−0.01446 (12)	0.1277 (8)
O12A	0.5719 (3)	0.0006 (2)	0.09493 (11)	0.1222 (8)
H1A	0.4401	0.0007	0.0614	0.25 (2)*
O21A	0.8640 (2)	0.0145 (2)	0.33072 (11)	0.1139 (7)
C1B	0.8087 (3)	0.3534 (3)	0.13578 (17)	0.0841 (8)
C2B	0.8061 (3)	0.3390 (2)	0.05543 (17)	0.0844 (8)
C3B	0.6716 (4)	0.3333 (3)	0.00966 (18)	0.1099 (10)
H3B	0.6723	0.3244	−0.0439	0.132*
C4B	0.5353 (4)	0.3409 (3)	0.0433 (2)	0.1279 (12)
H4B	0.4437	0.3365	0.0122	0.154*
C5B	0.5328 (4)	0.3548 (3)	0.1219 (3)	0.1298 (12)
H5B	0.4404	0.3600	0.1442	0.156*
C6B	0.6677 (4)	0.3611 (3)	0.16708 (19)	0.1104 (10)
H6B	0.6657	0.3708	0.2205	0.132*
C11B	0.9523 (3)	0.3591 (2)	0.18385 (16)	0.0854 (8)
H11B	1.0443	0.3642	0.1574	0.103*
C12B	0.9690 (4)	0.3580 (3)	0.25923 (17)	0.0977 (9)
H12B	0.8789	0.3525	0.2872	0.117*
C13B	1.1196 (4)	0.3646 (3)	0.30273 (17)	0.0923 (9)
C21B	0.9524 (3)	0.3149 (3)	−0.05520 (14)	0.0963 (9)
H21A	0.9373	0.3875	−0.0815	0.116*
H21B	0.8675	0.2375	−0.0743	0.116*
C22B	1.1154 (3)	0.3049 (3)	−0.06990 (16)	0.1147 (11)
H22D	1.1984	0.3826	−0.0517	0.172*
H22E	1.1229	0.2920	−0.1245	0.172*
H22F	1.1296	0.2335	−0.0430	0.172*
O11B	1.1124 (2)	0.34918 (19)	0.37500 (11)	0.1127 (7)
O12B	1.2469 (3)	0.38339 (19)	0.26725 (10)	0.1123 (7)
H1B	1.3781	0.3768	0.3049	0.27 (2)*
O21B	0.9463 (2)	0.33174 (18)	0.02649 (10)	0.0960 (6)
C1C	0.2034 (3)	0.6762 (2)	0.41845 (17)	0.0830 (8)
C2C	0.2154 (4)	0.6967 (3)	0.33951 (17)	0.0885 (8)
C3C	0.0860 (4)	0.7036 (3)	0.29377 (18)	0.1111 (10)
H3C	0.0964	0.7178	0.2412	0.133*
C4C	−0.0592 (4)	0.6896 (3)	0.3261 (3)	0.1266 (12)
H4C	−0.1471	0.6943	0.2952	0.152*
C5C	−0.0753 (4)	0.6686 (3)	0.4034 (3)	0.1223 (12)
H5C	−0.1739	0.6587	0.4250	0.147*
C6C	0.0539 (4)	0.6624 (3)	0.44855 (18)	0.1069 (10)
H6C	0.0419	0.6486	0.5011	0.128*
C11C	0.3410 (4)	0.6665 (3)	0.46511 (16)	0.0891 (8)
H11C	0.4356	0.6781	0.4395	0.107*
C12C	0.3486 (4)	0.6433 (3)	0.53937 (17)	0.0999 (9)
H12C	0.2561	0.6314	0.5667	0.120*
C13C	0.4941 (4)	0.6352 (3)	0.58122 (18)	0.0996 (9)
C21C	0.3819 (3)	0.7144 (3)	0.23043 (15)	0.1158 (11)
H21C	0.3726	0.7942	0.2117	0.139*
H21D	0.2981	0.6435	0.2036	0.139*
C22C	0.5435 (4)	0.7062 (3)	0.21622 (17)	0.1325 (12)
H22A	0.6254	0.7781	0.2417	0.199*
H22B	0.5579	0.7072	0.1615	0.199*
H22C	0.5522	0.6279	0.2362	0.199*
O11C	0.4849 (2)	0.6081 (2)	0.65176 (12)	0.1326 (9)
O12C	0.6235 (3)	0.6569 (2)	0.54658 (10)	0.1160 (7)
H1C	0.7462	0.6440	0.5835	0.201 (15)*
O21C	0.3641 (2)	0.70890 (19)	0.31218 (10)	0.1068 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.106 (2)	0.089 (2)	0.081 (2)	0.0312 (18)	0.006 (2)	0.0055 (17)
C2A	0.098 (2)	0.102 (3)	0.087 (2)	0.0349 (19)	0.003 (2)	0.0014 (18)
C3A	0.112 (2)	0.149 (3)	0.101 (2)	0.052 (2)	−0.014 (2)	0.003 (2)
C4A	0.109 (3)	0.145 (3)	0.153 (4)	0.050 (2)	−0.011 (3)	−0.002 (3)
C5A	0.108 (3)	0.145 (3)	0.146 (4)	0.045 (2)	0.023 (3)	0.003 (3)
C6A	0.120 (3)	0.118 (3)	0.111 (3)	0.036 (2)	0.019 (3)	0.001 (2)
C11A	0.142 (3)	0.083 (2)	0.070 (2)	0.0325 (19)	0.013 (2)	0.0074 (17)
C12A	0.140 (3)	0.099 (3)	0.087 (2)	0.035 (2)	0.024 (2)	0.0069 (19)
C13A	0.131 (3)	0.091 (3)	0.069 (2)	0.025 (2)	−0.001 (2)	0.0042 (18)
C21A	0.143 (3)	0.171 (3)	0.076 (2)	0.062 (2)	0.007 (2)	0.004 (2)
C22A	0.124 (3)	0.212 (4)	0.121 (3)	0.061 (3)	0.022 (2)	0.003 (3)
O11A	0.1470 (18)	0.155 (2)	0.0712 (14)	0.0362 (14)	0.0076 (14)	0.0013 (13)
O12A	0.1454 (19)	0.151 (2)	0.0690 (14)	0.0458 (15)	0.0129 (14)	0.0118 (12)
O21A	0.1052 (15)	0.161 (2)	0.0768 (14)	0.0465 (13)	0.0001 (12)	0.0059 (12)
C1B	0.088 (2)	0.089 (2)	0.078 (2)	0.0329 (16)	0.0091 (18)	0.0096 (16)
C2B	0.081 (2)	0.095 (2)	0.077 (2)	0.0292 (17)	0.0028 (18)	0.0045 (16)
C3B	0.090 (2)	0.146 (3)	0.095 (2)	0.043 (2)	−0.009 (2)	0.0045 (19)
C4B	0.092 (2)	0.158 (3)	0.136 (3)	0.045 (2)	−0.005 (2)	0.016 (3)
C5B	0.094 (3)	0.165 (4)	0.140 (3)	0.053 (2)	0.024 (3)	0.017 (3)
C6B	0.114 (2)	0.127 (3)	0.097 (2)	0.046 (2)	0.024 (2)	0.0127 (19)
C11B	0.102 (2)	0.085 (2)	0.071 (2)	0.0313 (17)	0.0058 (17)	0.0053 (15)
C12B	0.117 (3)	0.109 (3)	0.069 (2)	0.0397 (19)	0.0133 (19)	0.0035 (17)
C13B	0.117 (3)	0.094 (2)	0.066 (2)	0.037 (2)	−0.001 (2)	−0.0010 (17)
C21B	0.101 (2)	0.110 (3)	0.071 (2)	0.0257 (18)	−0.0009 (16)	0.0052 (16)
C22B	0.111 (2)	0.138 (3)	0.105 (2)	0.053 (2)	0.0202 (19)	0.004 (2)
O11B	0.1368 (17)	0.147 (2)	0.0601 (13)	0.0539 (14)	0.0053 (12)	0.0068 (12)
O12B	0.1163 (16)	0.146 (2)	0.0698 (14)	0.0353 (14)	0.0081 (12)	0.0161 (11)
O21B	0.0953 (13)	0.1299 (17)	0.0677 (13)	0.0447 (11)	−0.0014 (10)	−0.0007 (10)
C1C	0.088 (2)	0.087 (2)	0.075 (2)	0.0294 (16)	0.0045 (18)	0.0030 (15)
C2C	0.087 (2)	0.099 (2)	0.079 (2)	0.0297 (17)	−0.0009 (19)	−0.0010 (17)
C3C	0.105 (2)	0.144 (3)	0.090 (2)	0.050 (2)	−0.007 (2)	0.0064 (19)
C4C	0.101 (3)	0.141 (3)	0.143 (3)	0.048 (2)	−0.005 (2)	0.003 (3)
C5C	0.095 (3)	0.129 (3)	0.146 (3)	0.038 (2)	0.021 (3)	0.009 (3)
C6C	0.108 (2)	0.115 (3)	0.102 (2)	0.039 (2)	0.022 (2)	0.0119 (19)
C11C	0.105 (2)	0.095 (2)	0.0667 (19)	0.0320 (17)	0.0093 (17)	0.0047 (16)
C12C	0.104 (2)	0.118 (3)	0.075 (2)	0.0309 (19)	0.0115 (19)	0.0067 (18)
C13C	0.112 (3)	0.112 (3)	0.067 (2)	0.026 (2)	0.006 (2)	0.0026 (18)
C21C	0.120 (2)	0.158 (3)	0.075 (2)	0.052 (2)	0.0100 (18)	0.0235 (19)
C22C	0.115 (2)	0.183 (4)	0.111 (3)	0.060 (2)	0.028 (2)	0.027 (2)
O11C	0.1280 (17)	0.194 (2)	0.0659 (14)	0.0362 (15)	0.0078 (13)	0.0279 (14)
O12C	0.1171 (16)	0.164 (2)	0.0708 (14)	0.0500 (14)	0.0059 (12)	0.0120 (12)
O21C	0.0939 (14)	0.159 (2)	0.0701 (13)	0.0436 (12)	0.0044 (11)	0.0129 (11)

Geometric parameters (Å, º)

C1A—C2A	1.389 (3)	C11B—H11B	0.9300
C1A—C6A	1.394 (4)	C12B—C13B	1.463 (4)
C1A—C11A	1.470 (4)	C12B—H12B	0.9300
C2A—O21A	1.368 (3)	C13B—O12B	1.256 (3)
C2A—C3A	1.370 (4)	C13B—O11B	1.267 (3)
C3A—C4A	1.371 (4)	C21B—O21B	1.427 (2)
C3A—H3A	0.9300	C21B—C22B	1.498 (3)
C4A—C5A	1.366 (4)	C21B—H21A	0.9700
C4A—H4A	0.9300	C21B—H21B	0.9700
C5A—C6A	1.367 (4)	C22B—H22D	0.9600
C5A—H5A	0.9300	C22B—H22E	0.9600
C6A—H6A	0.9300	C22B—H22F	0.9600
C11A—C12A	1.285 (3)	O12B—H1B	1.3137
C11A—H11A	0.9300	C1C—C2C	1.392 (3)
C12A—C13A	1.487 (4)	C1C—C6C	1.394 (3)
C12A—H12A	0.9300	C1C—C11C	1.449 (3)
C13A—O11A	1.244 (3)	C2C—O21C	1.370 (3)
C13A—O12A	1.266 (3)	C2C—C3C	1.372 (3)
C21A—O21A	1.425 (3)	C3C—C4C	1.375 (4)
C21A—C22A	1.472 (4)	C3C—H3C	0.9300
C21A—H21E	0.9700	C4C—C5C	1.366 (4)
C21A—H21F	0.9700	C4C—H4C	0.9300
C22A—H22G	0.9600	C5C—C6C	1.362 (4)
C22A—H22H	0.9600	C5C—H5C	0.9300
C22A—H22I	0.9600	C6C—H6C	0.9300
O12A—H1A	1.2645	C11C—C12C	1.317 (3)
C1B—C2B	1.394 (3)	C11C—H11C	0.9300
C1B—C6B	1.396 (3)	C12C—C13C	1.461 (4)
C1B—C11B	1.454 (3)	C12C—H12C	0.9300
C2B—C3B	1.368 (3)	C13C—O12C	1.261 (3)
C2B—O21B	1.371 (3)	C13C—O11C	1.262 (3)
C3B—C4B	1.376 (3)	C21C—O21C	1.430 (3)
C3B—H3B	0.9300	C21C—C22C	1.476 (3)
C4B—C5B	1.366 (4)	C21C—H21C	0.9700
C4B—H4B	0.9300	C21C—H21D	0.9700
C5B—C6B	1.364 (4)	C22C—H22A	0.9600
C5B—H5B	0.9300	C22C—H22B	0.9600
C6B—H6B	0.9300	C22C—H22C	0.9600
C11B—C12B	1.306 (3)	O12C—H1C	1.2714
C2A—C1A—C6A	117.3 (3)	C11B—C12B—C13B	124.5 (3)
C2A—C1A—C11A	119.7 (3)	C11B—C12B—H12B	117.7
C6A—C1A—C11A	123.0 (3)	C13B—C12B—H12B	117.7
O21A—C2A—C3A	123.7 (3)	O12B—C13B—O11B	123.7 (3)
O21A—C2A—C1A	115.3 (3)	O12B—C13B—C12B	119.3 (3)
C3A—C2A—C1A	121.0 (3)	O11B—C13B—C12B	117.0 (3)
C2A—C3A—C4A	119.8 (3)	O21B—C21B—C22B	107.3 (2)
C2A—C3A—H3A	120.1	O21B—C21B—H21A	110.2
C4A—C3A—H3A	120.1	C22B—C21B—H21A	110.2
C5A—C4A—C3A	121.0 (4)	O21B—C21B—H21B	110.2
C5A—C4A—H4A	119.5	C22B—C21B—H21B	110.2
C3A—C4A—H4A	119.5	H21A—C21B—H21B	108.5
C4A—C5A—C6A	119.0 (3)	C21B—C22B—H22D	109.5
C4A—C5A—H5A	120.5	C21B—C22B—H22E	109.5
C6A—C5A—H5A	120.5	H22D—C22B—H22E	109.5
C5A—C6A—C1A	121.9 (3)	C21B—C22B—H22F	109.5
C5A—C6A—H6A	119.0	H22D—C22B—H22F	109.5
C1A—C6A—H6A	119.0	H22E—C22B—H22F	109.5
C12A—C11A—C1A	127.3 (3)	C13B—O12B—H1B	119.2
C12A—C11A—H11A	116.4	C2B—O21B—C21B	118.8 (2)
C1A—C11A—H11A	116.4	C2C—C1C—C6C	116.9 (3)
C11A—C12A—C13A	123.5 (3)	C2C—C1C—C11C	120.2 (3)
C11A—C12A—H12A	118.3	C6C—C1C—C11C	122.9 (3)
C13A—C12A—H12A	118.3	O21C—C2C—C3C	123.6 (3)
O11A—C13A—O12A	123.6 (3)	O21C—C2C—C1C	115.0 (3)
O11A—C13A—C12A	117.2 (3)	C3C—C2C—C1C	121.4 (3)
O12A—C13A—C12A	119.2 (3)	C2C—C3C—C4C	119.7 (3)
O21A—C21A—C22A	108.0 (3)	C2C—C3C—H3C	120.2
O21A—C21A—H21E	110.1	C4C—C3C—H3C	120.2
C22A—C21A—H21E	110.1	C5C—C4C—C3C	120.4 (3)
O21A—C21A—H21F	110.1	C5C—C4C—H4C	119.8
C22A—C21A—H21F	110.1	C3C—C4C—H4C	119.8
H21E—C21A—H21F	108.4	C6C—C5C—C4C	119.6 (3)
C21A—C22A—H22G	109.5	C6C—C5C—H5C	120.2
C21A—C22A—H22H	109.5	C4C—C5C—H5C	120.2
H22G—C22A—H22H	109.5	C5C—C6C—C1C	122.0 (3)
C21A—C22A—H22I	109.5	C5C—C6C—H6C	119.0
H22G—C22A—H22I	109.5	C1C—C6C—H6C	119.0
H22H—C22A—H22I	109.5	C12C—C11C—C1C	128.0 (3)
C13A—O12A—H1A	121.5	C12C—C11C—H11C	116.0
C2A—O21A—C21A	119.2 (2)	C1C—C11C—H11C	116.0
C2B—C1B—C6B	116.8 (3)	C11C—C12C—C13C	123.7 (3)
C2B—C1B—C11B	120.9 (3)	C11C—C12C—H12C	118.1
C6B—C1B—C11B	122.3 (3)	C13C—C12C—H12C	118.1
C3B—C2B—O21B	123.2 (3)	O12C—C13C—O11C	122.5 (3)
C3B—C2B—C1B	121.3 (3)	O12C—C13C—C12C	119.6 (3)
O21B—C2B—C1B	115.4 (3)	O11C—C13C—C12C	117.9 (3)
C2B—C3B—C4B	119.6 (3)	O21C—C21C—C22C	107.5 (2)
C2B—C3B—H3B	120.2	O21C—C21C—H21C	110.2
C4B—C3B—H3B	120.2	C22C—C21C—H21C	110.2
C5B—C4B—C3B	120.9 (3)	O21C—C21C—H21D	110.2
C5B—C4B—H4B	119.6	C22C—C21C—H21D	110.2
C3B—C4B—H4B	119.6	H21C—C21C—H21D	108.5
C6B—C5B—C4B	119.2 (3)	C21C—C22C—H22A	109.5
C6B—C5B—H5B	120.4	C21C—C22C—H22B	109.5
C4B—C5B—H5B	120.4	H22A—C22C—H22B	109.5
C5B—C6B—C1B	122.2 (3)	C21C—C22C—H22C	109.5
C5B—C6B—H6B	118.9	H22A—C22C—H22C	109.5
C1B—C6B—H6B	118.9	H22B—C22C—H22C	109.5
C12B—C11B—C1B	128.5 (3)	C13C—O12C—H1C	118.1
C12B—C11B—H11B	115.8	C2C—O21C—C21C	118.8 (2)
C1B—C11B—H11B	115.8
C6A—C1A—C2A—O21A	179.9 (2)	C11B—C1B—C6B—C5B	−179.6 (3)
C11A—C1A—C2A—O21A	0.4 (4)	C2B—C1B—C11B—C12B	−171.7 (3)
C6A—C1A—C2A—C3A	0.1 (4)	C6B—C1B—C11B—C12B	7.9 (5)
C11A—C1A—C2A—C3A	−179.4 (3)	C1B—C11B—C12B—C13B	−179.7 (3)
O21A—C2A—C3A—C4A	−179.7 (3)	C11B—C12B—C13B—O12B	6.2 (4)
C1A—C2A—C3A—C4A	0.0 (5)	C11B—C12B—C13B—O11B	−172.9 (3)
C2A—C3A—C4A—C5A	0.0 (5)	C3B—C2B—O21B—C21B	−1.3 (4)
C3A—C4A—C5A—C6A	−0.3 (6)	C1B—C2B—O21B—C21B	179.0 (2)
C4A—C5A—C6A—C1A	0.4 (5)	C22B—C21B—O21B—C2B	−177.7 (2)
C2A—C1A—C6A—C5A	−0.4 (5)	C6C—C1C—C2C—O21C	−179.6 (2)
C11A—C1A—C6A—C5A	179.2 (3)	C11C—C1C—C2C—O21C	−1.3 (4)
C2A—C1A—C11A—C12A	−177.0 (3)	C6C—C1C—C2C—C3C	0.3 (4)
C6A—C1A—C11A—C12A	3.4 (5)	C11C—C1C—C2C—C3C	178.7 (2)
C1A—C11A—C12A—C13A	178.5 (3)	O21C—C2C—C3C—C4C	179.7 (3)
C11A—C12A—C13A—O11A	−180.0 (3)	C1C—C2C—C3C—C4C	−0.3 (5)
C11A—C12A—C13A—O12A	0.0 (5)	C2C—C3C—C4C—C5C	−0.1 (5)
C3A—C2A—O21A—C21A	1.3 (4)	C3C—C4C—C5C—C6C	0.4 (5)
C1A—C2A—O21A—C21A	−178.5 (2)	C4C—C5C—C6C—C1C	−0.3 (5)
C22A—C21A—O21A—C2A	177.4 (3)	C2C—C1C—C6C—C5C	0.0 (4)
C6B—C1B—C2B—C3B	0.2 (4)	C11C—C1C—C6C—C5C	−178.3 (3)
C11B—C1B—C2B—C3B	179.9 (3)	C2C—C1C—C11C—C12C	−177.6 (3)
C6B—C1B—C2B—O21B	180.0 (2)	C6C—C1C—C11C—C12C	0.7 (4)
C11B—C1B—C2B—O21B	−0.4 (4)	C1C—C11C—C12C—C13C	179.9 (3)
O21B—C2B—C3B—C4B	179.8 (3)	C11C—C12C—C13C—O12C	3.3 (5)
C1B—C2B—C3B—C4B	−0.5 (4)	C11C—C12C—C13C—O11C	−177.6 (3)
C2B—C3B—C4B—C5B	0.4 (5)	C3C—C2C—O21C—C21C	−7.6 (4)
C3B—C4B—C5B—C6B	−0.1 (6)	C1C—C2C—O21C—C21C	172.4 (2)
C4B—C5B—C6B—C1B	−0.2 (5)	C22C—C21C—O21C—C2C	−171.0 (2)
C2B—C1B—C6B—C5B	0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12C—H1C···O11B^i	1.27	1.38	2.640 (3)	171
O12B—H1B···O11C^i	1.31	1.34	2.646 (3)	170
O12A—H1A···O11A^ii	1.26	1.38	2.630 (3)	170

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

(d6h_s) (E)-3-(2-Ethoxyphenyl)propenoic acid and trans-2,4-bis(2-ethoxyphenyl)-trans-1,3-cyclobutane-dicarboxylic acid

Crystal data

2.738(C11H12O3)·0.131(C22H24O6)	Z = 2
Mr = 576.62	F(000) = 612
Triclinic, P1	Dx = 1.247 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6759 (11) Å	Cell parameters from 781 reflections
b = 11.0003 (13) Å	θ = 2.3–21.4°
c = 17.299 (2) Å	µ = 0.09 mm^−1
α = 92.552 (3)°	T = 293 K
β = 92.347 (2)°	Irregular, white
γ = 111.155 (3)°	0.38 × 0.33 × 0.26 mm
V = 1535.3 (3) Å^3

Data collection

Bruker SMART 1K diffractometer	2192 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 25.0°, θmin = 1.2°
phi and ω scans	h = −10→10
8251 measured reflections	k = −11→13
5391 independent reflections	l = −20→14

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)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.220	w = 1/[σ^2(Fo^2) + (0.1128P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max < 0.001
5391 reflections	Δρmax = 0.19 e Å^−3
391 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

Special details

Experimental. The following alerts are triggered when using the ACTA-C CIF validation software.

PLAT301_ALERT_3_B Main Residue Disorder ························. 40.00 Perc. PLAT432_ALERT_2_B Short Inter X···Y Contact C3C.. C4D.. 3.05 A ng. PLAT432_ALERT_2_B Short Inter X···Y Contact C4C.. C3D.. 3.07 A ng. PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ···.. 28 PLAT340_ALERT_3_C Low Bond Precision on C—C bonds (x 1000) Ang ··· 6 PLAT432_ALERT_2_C Short Inter X···Y Contact C3C.. C3D.. 3.13 A ng. —— Authors comment: The assymetric unit consists of a mixture of the monomer and dimer. The short contacts are most probably due to the dimer not being properly optimized for the crystal structure at this point. Coordinates for the dimer molecule at a higher conversion stage was used as a starting point for the refinement. The dimer was also refined isotropically as a rigid body. This is necessary as the dimer is only present in about 4–5% occupancy (4% dimer occupancy = 8% of monomer consumed).

PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ···. 41 Perc. ——- Authors comment: The crystal was exposed to 6 h to UV light allowing some reaction to occur. This has most probably caused a certain amount of disorder leading to higher angle reflections having lower intensity than expected·The number of observed reflections has most probably decreased as a consequence.

PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ···. ? —— Authors commment: Our moiety formula is correct as it takes the occupancy of the dimer and monomer molecules into account.

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	Occ. (<1)
C1A	1.0151 (6)	0.0304 (4)	0.2213 (2)	0.0733 (12)	0.869 (3)
C2A	1.0109 (6)	0.0251 (4)	0.3015 (2)	0.0761 (12)	0.869 (3)
C3A	1.1502 (6)	0.0346 (4)	0.3466 (3)	0.0924 (14)	0.869 (3)
H3A	1.1462	0.0325	0.4002	0.111*	0.869 (3)
C4A	1.2944 (6)	0.0472 (5)	0.3126 (4)	0.1040 (16)	0.869 (3)
H4A	1.3873	0.0515	0.3430	0.125*	0.869 (3)
C5A	1.3022 (7)	0.0535 (5)	0.2333 (4)	0.1062 (17)	0.869 (3)
H5A	1.4009	0.0647	0.2102	0.127*	0.869 (3)
C6A	1.1624 (8)	0.0431 (5)	0.1888 (3)	0.0976 (15)	0.869 (3)
H6A	1.1673	0.0446	0.1353	0.117*	0.869 (3)
C11A	0.8643 (5)	0.0194 (3)	0.1735 (2)	0.0738 (12)	0.869 (3)
H11A	0.7708	0.0117	0.2003	0.089*	0.869 (3)
C12A	0.8480 (6)	0.0194 (4)	0.0976 (2)	0.0814 (13)	0.869 (3)
H12A	0.9397	0.0272	0.0693	0.098*	0.869 (3)
C13A	0.6944 (6)	0.0077 (4)	0.0553 (3)	0.0809 (13)	0.869 (3)
C21A	0.8468 (7)	0.0093 (5)	0.4133 (2)	0.0951 (14)	0.869 (3)
H21C	0.9285	0.0874	0.4391	0.114*	0.869 (3)
H21D	0.8647	−0.0663	0.4326	0.114*	0.869 (3)
C22A	0.6766 (7)	0.0035 (6)	0.4279 (3)	0.1086 (16)	0.869 (3)
H22D	0.6604	0.0785	0.4083	0.163*	0.869 (3)
H22E	0.6624	0.0026	0.4827	0.163*	0.869 (3)
H22F	0.5972	−0.0745	0.4022	0.163*	0.869 (3)
O11A	0.6914 (4)	0.0087 (3)	−0.01701 (17)	0.0957 (10)	0.869 (3)
O12A	0.5711 (5)	−0.0035 (3)	0.09473 (19)	0.1040 (11)	0.869 (3)
H1A	0.4916	−0.0085	0.0657	0.156*	0.869 (3)
O21A	0.8606 (5)	0.0111 (4)	0.33080 (16)	0.0899 (9)	0.869 (3)
C1B	0.7939 (5)	0.3471 (4)	0.1306 (2)	0.0661 (10)	0.869 (3)
C2B	0.7929 (5)	0.3366 (4)	0.0494 (2)	0.0657 (10)	0.869 (3)
C3B	0.6538 (6)	0.3308 (4)	0.0043 (3)	0.0848 (14)	0.869 (3)
H3B	0.6531	0.3218	−0.0495	0.102*	0.869 (3)
C4B	0.5175 (6)	0.3384 (5)	0.0389 (3)	0.1009 (16)	0.869 (3)
H4B	0.4255	0.3358	0.0084	0.121*	0.869 (3)
C5B	0.5164 (7)	0.3497 (6)	0.1182 (4)	0.1037 (16)	0.869 (3)
H5B	0.4234	0.3536	0.1414	0.124*	0.869 (3)
C6B	0.6547 (6)	0.3553 (4)	0.1632 (3)	0.0861 (13)	0.869 (3)
H6B	0.6540	0.3648	0.2169	0.103*	0.869 (3)
C11B	0.9396 (5)	0.3533 (3)	0.1780 (2)	0.0636 (10)	0.869 (3)
H11B	1.0333	0.3595	0.1518	0.076*	0.869 (3)
C12B	0.9532 (5)	0.3510 (4)	0.2543 (2)	0.0736 (12)	0.869 (3)
H12B	0.8616	0.3445	0.2822	0.088*	0.869 (3)
C13B	1.1052 (6)	0.3584 (4)	0.2963 (2)	0.0724 (12)	0.869 (3)
C21B	0.9379 (6)	0.3138 (4)	−0.0625 (2)	0.0761 (12)	0.869 (3)
H21E	0.9277	0.3886	−0.0867	0.091*	0.869 (3)
H21F	0.8477	0.2359	−0.0832	0.091*	0.869 (3)
C22B	1.1002 (6)	0.3028 (5)	−0.0782 (2)	0.0921 (14)	0.869 (3)
H22G	1.1884	0.3815	−0.0589	0.138*	0.869 (3)
H22H	1.1067	0.2900	−0.1331	0.138*	0.869 (3)
H22I	1.1100	0.2299	−0.0528	0.138*	0.869 (3)
O11B	1.0958 (4)	0.3432 (3)	0.36910 (15)	0.0883 (10)	0.869 (3)
H1B	1.1862	0.3480	0.3881	0.132*	0.869 (3)
O12B	1.2360 (4)	0.3790 (3)	0.26206 (17)	0.0877 (9)	0.869 (3)
O21B	0.9329 (4)	0.3290 (3)	0.01970 (14)	0.0751 (8)	0.869 (3)
C1C	0.2163 (4)	0.6710 (3)	0.42390 (19)	0.0688 (9)
C2C	0.2291 (4)	0.6868 (3)	0.34529 (19)	0.0743 (10)
C3C	0.0957 (5)	0.6907 (4)	0.2992 (2)	0.0975 (12)
H3C	0.1049	0.7015	0.2464	0.117*
C4C	−0.0505 (5)	0.6785 (4)	0.3330 (3)	0.1070 (13)
H4C	−0.1406	0.6800	0.3026	0.128*
C5C	−0.0636 (6)	0.6640 (4)	0.4113 (3)	0.1041 (13)
H5C	−0.1617	0.6570	0.4338	0.125*
C6C	0.0680 (5)	0.6598 (3)	0.4562 (2)	0.0882 (11)
H6C	0.0580	0.6494	0.5091	0.106*
C11C	0.3570 (4)	0.6642 (3)	0.47092 (19)	0.0700 (9)
H11C	0.4524	0.6741	0.4451	0.084*
C12C	0.3643 (5)	0.6455 (3)	0.54595 (19)	0.0805 (10)
H12C	0.2720	0.6366	0.5739	0.097*
C13C	0.5116 (5)	0.6382 (3)	0.58652 (19)	0.0796 (11)
C21C	0.3944 (4)	0.7049 (4)	0.23477 (18)	0.0846 (11)
H21A	0.3861	0.7855	0.2180	0.102*
H21B	0.3080	0.6320	0.2068	0.102*
C22C	0.5601 (4)	0.7008 (4)	0.2197 (2)	0.0953 (12)
H22A	0.6443	0.7729	0.2481	0.143*
H22B	0.5769	0.7067	0.1653	0.143*
H22C	0.5662	0.6203	0.2360	0.143*
O11C	0.4971 (3)	0.6124 (3)	0.65788 (13)	0.1059 (9)
H1C	0.5846	0.6101	0.6763	0.159*
O12C	0.6431 (3)	0.6588 (2)	0.55318 (13)	0.0957 (8)
O21C	0.3774 (3)	0.6973 (2)	0.31633 (12)	0.0854 (7)
C1D	1.0193 (15)	0.0446 (10)	0.2376 (7)	0.078 (3)*	0.131 (3)
C2D	1.0034 (18)	0.0066 (12)	0.3131 (7)	0.078 (3)*	0.131 (3)
C3D	1.129 (2)	−0.0246 (15)	0.3525 (9)	0.078 (3)*	0.131 (3)
H3D	1.1161	−0.0523	0.4026	0.094*	0.131 (3)
C4D	1.271 (2)	−0.0131 (18)	0.3149 (10)	0.078 (3)*	0.131 (3)
H4D	1.3555	−0.0315	0.3409	0.094*	0.131 (3)
C5D	1.2909 (19)	0.0247 (18)	0.2406 (10)	0.078 (3)*	0.131 (3)
H5D	1.3862	0.0306	0.2158	0.094*	0.131 (3)
C6D	1.1654 (16)	0.0541 (14)	0.2029 (8)	0.078 (3)*	0.131 (3)
H6D	1.1792	0.0811	0.1526	0.094*	0.131 (3)
C11D	0.8894 (12)	0.0911 (8)	0.2048 (6)	0.078 (3)*	0.131 (3)
H11D	0.7790	0.0294	0.2146	0.094*	0.131 (3)
C12D	0.8940 (12)	0.1274 (9)	0.1198 (5)	0.078 (3)*	0.131 (3)
H12D	0.9920	0.1235	0.0952	0.094*	0.131 (3)
C13D	0.7332 (14)	0.0555 (10)	0.0702 (6)	0.078 (3)*	0.131 (3)
C21D	0.845 (2)	−0.0164 (18)	0.4253 (7)	0.078 (3)*	0.131 (3)
H21G	0.9355	0.0516	0.4542	0.094*	0.131 (3)
H21H	0.8485	−0.1004	0.4376	0.094*	0.131 (3)
C22D	0.681 (2)	−0.008 (2)	0.4465 (8)	0.078 (3)*	0.131 (3)
H22J	0.6687	−0.0181	0.5010	0.117*	0.131 (3)
H22K	0.5919	−0.0756	0.4177	0.117*	0.131 (3)
H22L	0.6785	0.0758	0.4342	0.117*	0.131 (3)
O11D	0.7562 (18)	0.0505 (13)	−0.0048 (6)	0.078 (3)*	0.131 (3)
H1D	0.6673	0.0113	−0.0288	0.117*	0.131 (3)
O12D	0.5962 (13)	0.0209 (12)	0.0952 (8)	0.078 (3)*	0.131 (3)
O21D	0.8578 (19)	−0.0007 (14)	0.3443 (7)	0.078 (3)*	0.131 (3)
C1E	0.7855 (16)	0.3239 (11)	0.1128 (7)	0.078 (3)*	0.131 (3)
C2E	0.7950 (19)	0.3461 (12)	0.0348 (7)	0.078 (3)*	0.131 (3)
C3E	0.669 (2)	0.3721 (16)	−0.0060 (9)	0.078 (3)*	0.131 (3)
H3E	0.6754	0.3869	−0.0584	0.094*	0.131 (3)
C4E	0.533 (2)	0.3754 (19)	0.0333 (11)	0.078 (3)*	0.131 (3)
H4E	0.4490	0.3926	0.0066	0.094*	0.131 (3)
C5E	0.522 (2)	0.3539 (19)	0.1104 (11)	0.078 (3)*	0.131 (3)
H5E	0.4311	0.3571	0.1362	0.094*	0.131 (3)
C6E	0.6475 (18)	0.3274 (15)	0.1497 (9)	0.078 (3)*	0.131 (3)
H6E	0.6393	0.3115	0.2021	0.094*	0.131 (3)
C11E	0.9129 (12)	0.2741 (8)	0.1470 (6)	0.078 (3)*	0.131 (3)
H11E	1.0244	0.3344	0.1378	0.094*	0.131 (3)
C12E	0.9060 (12)	0.2380 (9)	0.2321 (6)	0.078 (3)*	0.131 (3)
H12E	0.8065	0.2408	0.2558	0.094*	0.131 (3)
C13E	1.0633 (15)	0.3090 (10)	0.2832 (6)	0.078 (3)*	0.131 (3)
C21E	0.937 (2)	0.3347 (18)	−0.0810 (7)	0.078 (3)*	0.131 (3)
H21I	0.9376	0.4155	−0.1013	0.094*	0.131 (3)
H21J	0.8398	0.2637	−0.1028	0.094*	0.131 (3)
C22E	1.093 (2)	0.311 (2)	−0.1017 (7)	0.078 (3)*	0.131 (3)
H22M	1.0974	0.3046	−0.1571	0.117*	0.131 (3)
H22N	1.0915	0.2303	−0.0813	0.117*	0.131 (3)
H22O	1.1889	0.3814	−0.0799	0.117*	0.131 (3)
O11E	1.0390 (19)	0.2985 (13)	0.3569 (6)	0.078 (3)*	0.131 (3)
H1E	1.1262	0.3378	0.3823	0.117*	0.131 (3)
O12E	1.2002 (14)	0.3558 (11)	0.2574 (8)	0.078 (3)*	0.131 (3)
O21E	0.9371 (19)	0.3427 (13)	0.0023 (7)	0.078 (3)*	0.131 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.090 (3)	0.068 (3)	0.068 (3)	0.034 (2)	0.020 (3)	0.004 (2)
C2A	0.088 (3)	0.076 (3)	0.066 (3)	0.031 (2)	0.012 (3)	0.000 (2)
C3A	0.096 (3)	0.105 (4)	0.078 (3)	0.039 (3)	−0.003 (3)	0.004 (3)
C4A	0.088 (4)	0.109 (4)	0.122 (5)	0.044 (3)	0.009 (3)	0.000 (3)
C5A	0.105 (4)	0.102 (4)	0.118 (5)	0.042 (3)	0.037 (4)	0.007 (3)
C6A	0.116 (4)	0.101 (3)	0.082 (3)	0.045 (3)	0.024 (3)	0.003 (3)
C11A	0.102 (3)	0.061 (2)	0.060 (3)	0.030 (2)	0.015 (2)	0.007 (2)
C12A	0.113 (4)	0.078 (3)	0.058 (3)	0.038 (3)	0.019 (3)	0.008 (2)
C13A	0.112 (4)	0.074 (3)	0.060 (3)	0.035 (3)	0.022 (3)	0.009 (2)
C21A	0.113 (4)	0.124 (4)	0.054 (3)	0.050 (3)	0.007 (3)	0.004 (2)
C22A	0.101 (4)	0.154 (4)	0.076 (3)	0.052 (3)	0.017 (3)	0.001 (3)
O11A	0.115 (3)	0.113 (2)	0.0525 (18)	0.0311 (19)	0.0157 (17)	0.0107 (16)
O12A	0.131 (3)	0.120 (3)	0.0630 (19)	0.046 (2)	0.023 (2)	0.0136 (17)
O21A	0.092 (2)	0.126 (2)	0.0528 (18)	0.0407 (17)	0.0073 (16)	0.0066 (16)
C1B	0.079 (3)	0.068 (2)	0.061 (3)	0.036 (2)	0.012 (2)	0.0075 (19)
C2B	0.076 (3)	0.073 (3)	0.053 (2)	0.033 (2)	0.007 (2)	0.0068 (19)
C3B	0.080 (3)	0.111 (4)	0.065 (3)	0.039 (3)	−0.009 (3)	0.003 (2)
C4B	0.086 (3)	0.128 (4)	0.099 (4)	0.051 (3)	0.005 (3)	0.007 (3)
C5B	0.093 (4)	0.122 (4)	0.110 (4)	0.053 (3)	0.029 (3)	0.008 (3)
C6B	0.097 (3)	0.097 (3)	0.075 (3)	0.046 (3)	0.017 (3)	0.011 (2)
C11B	0.079 (3)	0.068 (2)	0.052 (2)	0.036 (2)	0.007 (2)	0.0053 (18)
C12B	0.085 (3)	0.091 (3)	0.053 (2)	0.042 (2)	0.002 (2)	0.002 (2)
C13B	0.111 (4)	0.070 (3)	0.040 (2)	0.036 (2)	0.008 (2)	0.0067 (19)
C21B	0.088 (3)	0.094 (3)	0.046 (2)	0.032 (2)	0.003 (2)	0.003 (2)
C22B	0.099 (3)	0.126 (4)	0.067 (3)	0.057 (3)	0.021 (3)	0.006 (3)
O11B	0.108 (3)	0.115 (2)	0.0489 (17)	0.049 (2)	0.0030 (16)	0.0063 (15)
O12B	0.102 (2)	0.112 (2)	0.0516 (17)	0.0392 (18)	0.0158 (17)	0.0170 (15)
O21B	0.0819 (18)	0.107 (2)	0.0458 (16)	0.0455 (15)	0.0036 (14)	0.0015 (14)
C1C	0.075 (2)	0.074 (2)	0.062 (2)	0.0319 (18)	0.0077 (19)	−0.0015 (17)
C2C	0.078 (2)	0.087 (2)	0.055 (2)	0.0269 (19)	0.010 (2)	−0.0002 (18)
C3C	0.089 (3)	0.138 (3)	0.072 (3)	0.051 (2)	−0.001 (2)	0.002 (2)
C4C	0.091 (3)	0.134 (4)	0.103 (4)	0.049 (3)	0.004 (3)	0.003 (3)
C5C	0.095 (3)	0.116 (3)	0.109 (4)	0.044 (3)	0.031 (3)	0.007 (3)
C6C	0.098 (3)	0.099 (3)	0.078 (3)	0.045 (2)	0.025 (2)	0.010 (2)
C11C	0.082 (2)	0.075 (2)	0.056 (2)	0.0313 (18)	0.0084 (19)	−0.0003 (17)
C12C	0.092 (3)	0.099 (3)	0.057 (2)	0.040 (2)	0.015 (2)	0.009 (2)
C13C	0.112 (3)	0.085 (2)	0.045 (2)	0.039 (2)	0.004 (2)	0.0030 (18)
C21C	0.090 (3)	0.115 (3)	0.055 (2)	0.043 (2)	0.0115 (19)	0.015 (2)
C22C	0.096 (3)	0.128 (3)	0.070 (2)	0.047 (2)	0.023 (2)	0.012 (2)
O11C	0.109 (2)	0.152 (2)	0.0576 (16)	0.0455 (17)	0.0068 (14)	0.0249 (15)
O12C	0.111 (2)	0.130 (2)	0.0551 (15)	0.0534 (17)	0.0189 (15)	0.0098 (14)
O21C	0.0802 (16)	0.131 (2)	0.0475 (13)	0.0408 (14)	0.0061 (12)	0.0076 (13)

Geometric parameters (Å, º)

C1A—C6A	1.380 (5)	C12C—C13C	1.462 (5)
C1A—C2A	1.394 (5)	C12C—H12C	0.9300
C1A—C11A	1.482 (6)	C13C—O12C	1.251 (4)
C2A—O21A	1.377 (4)	C13C—O11C	1.280 (4)
C2A—C3A	1.380 (6)	C21C—O21C	1.428 (3)
C3A—C4A	1.368 (6)	C21C—C22C	1.488 (4)
C3A—H3A	0.9300	C21C—H21A	0.9700
C4A—C5A	1.380 (6)	C21C—H21B	0.9700
C4A—H4A	0.9300	C22C—H22A	0.9600
C5A—C6A	1.375 (6)	C22C—H22B	0.9600
C5A—H5A	0.9300	C22C—H22C	0.9600
C6A—H6A	0.9300	O11C—H1C	0.8200
C11A—C12A	1.316 (5)	C1D—C2D	1.3865
C11A—H11A	0.9300	C1D—C6D	1.3961
C12A—C13A	1.454 (6)	C1D—C11D	1.4979
C12A—H12A	0.9300	C2D—O21D	1.3716
C13A—O11A	1.251 (4)	C2D—C3D	1.4116
C13A—O12A	1.264 (5)	C3D—C4D	1.3885
C21A—O21A	1.437 (4)	C3D—H3D	0.9300
C21A—C22A	1.488 (6)	C4D—C5D	1.3674
C21A—H21C	0.9700	C4D—H4D	0.9300
C21A—H21D	0.9700	C5D—C6D	1.3890
C22A—H22D	0.9600	C5D—H5D	0.9300
C22A—H22E	0.9600	C6D—H6D	0.9300
C22A—H22F	0.9600	C11D—C12D	1.5394
O12A—H1A	0.8200	C11D—C12E	1.6166
C1B—C6B	1.384 (5)	C11D—H11D	0.9800
C1B—C2B	1.403 (5)	C12D—C13D	1.5337
C1B—C11B	1.458 (5)	C12D—C11E	1.6084
C2B—O21B	1.367 (4)	C12D—H12D	0.9800
C2B—C3B	1.390 (5)	C13D—O12D	1.2148
C3B—C4B	1.374 (5)	C13D—O11D	1.3234
C3B—H3B	0.9300	C21D—O21D	1.4229
C4B—C5B	1.373 (6)	C21D—C22D	1.5151
C4B—H4B	0.9300	C21D—H21G	0.9700
C5B—C6B	1.385 (6)	C21D—H21H	0.9700
C5B—H5B	0.9300	C22D—H22J	0.9600
C6B—H6B	0.9300	C22D—H22K	0.9600
C11B—C12B	1.321 (5)	C22D—H22L	0.9600
C11B—H11B	0.9300	O11D—H1D	0.8200
C12B—C13B	1.454 (5)	C1E—C2E	1.3829
C12B—H12B	0.9300	C1E—C6E	1.3919
C13B—O12B	1.254 (4)	C1E—C11E	1.5118
C13B—O11B	1.279 (4)	C2E—O21E	1.3878
C21B—O21B	1.429 (4)	C2E—C3E	1.3985
C21B—C22B	1.491 (5)	C3E—C4E	1.3933
C21B—H21E	0.9700	C3E—H3E	0.9300
C21B—H21F	0.9700	C4E—C5E	1.3663
C22B—H22G	0.9600	C4E—H4E	0.9300
C22B—H22H	0.9600	C5E—C6E	1.3865
C22B—H22I	0.9600	C5E—H5E	0.9300
O11B—H1B	0.8200	C6E—H6E	0.9300
C1C—C2C	1.382 (4)	C11E—C12E	1.5393
C1C—C6C	1.391 (4)	C11E—H11E	0.9800
C1C—C11C	1.466 (4)	C12E—C13E	1.5245
C2C—O21C	1.368 (4)	C12E—H12E	0.9800
C2C—C3C	1.393 (5)	C13E—O12E	1.2245
C3C—C4C	1.383 (5)	C13E—O11E	1.3047
C3C—H3C	0.9300	C21E—O21E	1.4391
C4C—C5C	1.376 (5)	C21E—C22E	1.5213
C4C—H4C	0.9300	C21E—H21I	0.9700
C5C—C6C	1.369 (5)	C21E—H21J	0.9700
C5C—H5C	0.9300	C22E—H22M	0.9600
C6C—H6C	0.9300	C22E—H22N	0.9600
C11C—C12C	1.326 (4)	C22E—H22O	0.9600
C11C—H11C	0.9300	O11E—H1E	0.8200
C6A—C1A—C2A	117.5 (5)	O21C—C21C—C22C	106.9 (3)
C6A—C1A—C11A	122.2 (4)	O21C—C21C—H21A	110.3
C2A—C1A—C11A	120.3 (4)	C22C—C21C—H21A	110.3
O21A—C2A—C3A	124.0 (4)	O21C—C21C—H21B	110.3
O21A—C2A—C1A	115.2 (4)	C22C—C21C—H21B	110.3
C3A—C2A—C1A	120.9 (4)	H21A—C21C—H21B	108.6
C4A—C3A—C2A	120.1 (4)	C21C—C22C—H22A	109.5
C4A—C3A—H3A	120.0	C21C—C22C—H22B	109.5
C2A—C3A—H3A	120.0	H22A—C22C—H22B	109.5
C3A—C4A—C5A	120.2 (5)	C21C—C22C—H22C	109.5
C3A—C4A—H4A	119.9	H22A—C22C—H22C	109.5
C5A—C4A—H4A	119.9	H22B—C22C—H22C	109.5
C6A—C5A—C4A	119.2 (5)	C13C—O11C—H1C	109.5
C6A—C5A—H5A	120.4	C2C—O21C—C21C	119.0 (3)
C4A—C5A—H5A	120.4	C2D—C1D—C6D	117.6
C5A—C6A—C1A	122.0 (5)	C2D—C1D—C11D	116.5
C5A—C6A—H6A	119.0	C6D—C1D—C11D	125.3
C1A—C6A—H6A	119.0	O21D—C2D—C1D	115.0
C12A—C11A—C1A	127.3 (4)	O21D—C2D—C3D	124.0
C12A—C11A—H11A	116.3	C1D—C2D—C3D	121.0
C1A—C11A—H11A	116.3	C4D—C3D—C2D	118.8
C11A—C12A—C13A	123.6 (4)	C4D—C3D—H3D	120.6
C11A—C12A—H12A	118.2	C2D—C3D—H3D	120.6
C13A—C12A—H12A	118.2	C5D—C4D—C3D	121.6
O11A—C13A—O12A	124.0 (5)	C5D—C4D—H4D	119.2
O11A—C13A—C12A	118.8 (4)	C3D—C4D—H4D	119.2
O12A—C13A—C12A	117.2 (4)	C4D—C5D—C6D	118.6
O21A—C21A—C22A	106.8 (4)	C4D—C5D—H5D	120.7
O21A—C21A—H21C	110.4	C6D—C5D—H5D	120.7
C22A—C21A—H21C	110.4	C5D—C6D—C1D	122.5
O21A—C21A—H21D	110.4	C5D—C6D—H6D	118.7
C22A—C21A—H21D	110.4	C1D—C6D—H6D	118.7
H21C—C21A—H21D	108.6	C1D—C11D—C12D	119.2
C21A—C22A—H22D	109.5	C1D—C11D—C12E	116.5
C21A—C22A—H22E	109.5	C12D—C11D—C12E	89.6
H22D—C22A—H22E	109.5	C1D—C11D—H11D	110.0
C21A—C22A—H22F	109.5	C12D—C11D—H11D	110.0
H22D—C22A—H22F	109.5	C12E—C11D—H11D	110.0
H22E—C22A—H22F	109.5	C13D—C12D—C11D	114.6
C13A—O12A—H1A	109.5	C13D—C12D—C11E	112.4
C2A—O21A—C21A	118.8 (3)	C11D—C12D—C11E	90.4
C6B—C1B—C2B	117.7 (4)	C13D—C12D—H12D	112.6
C6B—C1B—C11B	121.8 (4)	C11D—C12D—H12D	112.6
C2B—C1B—C11B	120.5 (3)	C11E—C12D—H12D	112.6
O21B—C2B—C3B	123.8 (3)	O12D—C13D—O11D	122.4
O21B—C2B—C1B	115.8 (3)	O12D—C13D—C12D	124.0
C3B—C2B—C1B	120.4 (4)	O11D—C13D—C12D	113.0
C4B—C3B—C2B	120.1 (4)	O21D—C21D—C22D	107.7
C4B—C3B—H3B	119.9	O21D—C21D—H21G	110.2
C2B—C3B—H3B	119.9	C22D—C21D—H21G	110.2
C5B—C4B—C3B	120.4 (5)	O21D—C21D—H21H	110.2
C5B—C4B—H4B	119.8	C22D—C21D—H21H	110.2
C3B—C4B—H4B	119.8	H21G—C21D—H21H	108.5
C4B—C5B—C6B	119.5 (4)	C21D—C22D—H22J	109.5
C4B—C5B—H5B	120.2	C21D—C22D—H22K	109.5
C6B—C5B—H5B	120.2	H22J—C22D—H22K	109.5
C1B—C6B—C5B	121.8 (4)	C21D—C22D—H22L	109.5
C1B—C6B—H6B	119.1	H22J—C22D—H22L	109.5
C5B—C6B—H6B	119.1	H22K—C22D—H22L	109.5
C12B—C11B—C1B	127.1 (4)	C13D—O11D—H1D	109.5
C12B—C11B—H11B	116.4	C2D—O21D—C21D	118.0
C1B—C11B—H11B	116.4	C2E—C1E—C6E	118.5
C11B—C12B—C13B	122.9 (4)	C2E—C1E—C11E	115.6
C11B—C12B—H12B	118.6	C6E—C1E—C11E	124.9
C13B—C12B—H12B	118.6	C1E—C2E—O21E	115.2
O12B—C13B—O11B	123.2 (4)	C1E—C2E—C3E	120.7
O12B—C13B—C12B	120.9 (3)	O21E—C2E—C3E	124.1
O11B—C13B—C12B	115.9 (4)	C4E—C3E—C2E	119.0
O21B—C21B—C22B	107.1 (3)	C4E—C3E—H3E	120.5
O21B—C21B—H21E	110.3	C2E—C3E—H3E	120.5
C22B—C21B—H21E	110.3	C5E—C4E—C3E	121.3
O21B—C21B—H21F	110.3	C5E—C4E—H4E	119.4
C22B—C21B—H21F	110.3	C3E—C4E—H4E	119.4
H21E—C21B—H21F	108.5	C4E—C5E—C6E	119.0
C21B—C22B—H22G	109.5	C4E—C5E—H5E	120.5
C21B—C22B—H22H	109.5	C6E—C5E—H5E	120.5
H22G—C22B—H22H	109.5	C5E—C6E—C1E	121.6
C21B—C22B—H22I	109.5	C5E—C6E—H6E	119.2
H22G—C22B—H22I	109.5	C1E—C6E—H6E	119.2
H22H—C22B—H22I	109.5	C1E—C11E—C12E	119.6
C13B—O11B—H1B	109.5	C1E—C11E—C12D	116.7
C2B—O21B—C21B	118.6 (3)	C12E—C11E—C12D	89.9
C2C—C1C—C6C	118.7 (3)	C1E—C11E—H11E	109.7
C2C—C1C—C11C	119.7 (3)	C12E—C11E—H11E	109.7
C6C—C1C—C11C	121.5 (3)	C12D—C11E—H11E	109.7
O21C—C2C—C1C	116.5 (3)	C13E—C12E—C11E	115.4
O21C—C2C—C3C	122.9 (3)	C13E—C12E—C11D	112.1
C1C—C2C—C3C	120.6 (3)	C11E—C12E—C11D	90.1
C4C—C3C—C2C	119.3 (4)	C13E—C12E—H12E	112.5
C4C—C3C—H3C	120.4	C11E—C12E—H12E	112.5
C2C—C3C—H3C	120.4	C11D—C12E—H12E	112.5
C5C—C4C—C3C	120.4 (4)	O12E—C13E—O11E	123.8
C5C—C4C—H4C	119.8	O12E—C13E—C12E	123.0
C3C—C4C—H4C	119.8	O11E—C13E—C12E	112.5
C6C—C5C—C4C	120.0 (4)	O21E—C21E—C22E	107.3
C6C—C5C—H5C	120.0	O21E—C21E—H21I	110.3
C4C—C5C—H5C	120.0	C22E—C21E—H21I	110.3
C5C—C6C—C1C	120.9 (4)	O21E—C21E—H21J	110.3
C5C—C6C—H6C	119.5	C22E—C21E—H21J	110.3
C1C—C6C—H6C	119.5	H21I—C21E—H21J	108.5
C12C—C11C—C1C	127.6 (3)	C21E—C22E—H22M	109.5
C12C—C11C—H11C	116.2	C21E—C22E—H22N	109.5
C1C—C11C—H11C	116.2	H22M—C22E—H22N	109.5
C11C—C12C—C13C	122.7 (3)	C21E—C22E—H22O	109.5
C11C—C12C—H12C	118.7	H22M—C22E—H22O	109.5
C13C—C12C—H12C	118.7	H22N—C22E—H22O	109.5
O12C—C13C—O11C	123.0 (4)	C13E—O11E—H1E	109.5
O12C—C13C—C12C	121.4 (3)	C2E—O21E—C21E	117.6
O11C—C13C—C12C	115.6 (4)
C6A—C1A—C2A—O21A	−179.4 (3)	C6D—C1D—C2D—C3D	−1.6
C11A—C1A—C2A—O21A	−0.8 (5)	C11D—C1D—C2D—C3D	−172.7
C6A—C1A—C2A—C3A	1.1 (6)	O21D—C2D—C3D—C4D	−179.8
C11A—C1A—C2A—C3A	179.7 (4)	C1D—C2D—C3D—C4D	1.7
O21A—C2A—C3A—C4A	179.5 (4)	C2D—C3D—C4D—C5D	−1.5
C1A—C2A—C3A—C4A	−1.1 (6)	C3D—C4D—C5D—C6D	1.1
C2A—C3A—C4A—C5A	1.5 (7)	C4D—C5D—C6D—C1D	−1.0
C3A—C4A—C5A—C6A	−1.9 (7)	C2D—C1D—C6D—C5D	1.3
C4A—C5A—C6A—C1A	2.0 (7)	C11D—C1D—C6D—C5D	171.5
C2A—C1A—C6A—C5A	−1.6 (6)	C2D—C1D—C11D—C12D	−176.6
C11A—C1A—C6A—C5A	179.9 (4)	C6D—C1D—C11D—C12D	13.1
C6A—C1A—C11A—C12A	0.4 (6)	C2D—C1D—C11D—C12E	77.8
C2A—C1A—C11A—C12A	−178.1 (4)	C6D—C1D—C11D—C12E	−92.6
C1A—C11A—C12A—C13A	179.8 (4)	C1D—C11D—C12D—C13D	125.2
C11A—C12A—C13A—O11A	180.0 (4)	C12E—C11D—C12D—C13D	−114.3
C11A—C12A—C13A—O12A	−0.3 (6)	C1D—C11D—C12D—C11E	−119.8
C3A—C2A—O21A—C21A	1.5 (6)	C12E—C11D—C12D—C11E	0.7
C1A—C2A—O21A—C21A	−177.9 (3)	C11D—C12D—C13D—O12D	31.8
C22A—C21A—O21A—C2A	175.8 (3)	C11E—C12D—C13D—O12D	−69.5
C6B—C1B—C2B—O21B	179.9 (3)	C11D—C12D—C13D—O11D	−157.0
C11B—C1B—C2B—O21B	1.9 (5)	C11E—C12D—C13D—O11D	101.6
C6B—C1B—C2B—C3B	−1.9 (5)	C1D—C2D—O21D—C21D	−169.1
C11B—C1B—C2B—C3B	−180.0 (3)	C3D—C2D—O21D—C21D	12.3
O21B—C2B—C3B—C4B	179.5 (4)	C22D—C21D—O21D—C2D	174.3
C1B—C2B—C3B—C4B	1.5 (6)	C6E—C1E—C2E—O21E	179.2
C2B—C3B—C4B—C5B	−1.0 (7)	C11E—C1E—C2E—O21E	−11.3
C3B—C4B—C5B—C6B	0.9 (7)	C6E—C1E—C2E—C3E	0.2
C2B—C1B—C6B—C5B	1.8 (6)	C11E—C1E—C2E—C3E	169.8
C11B—C1B—C6B—C5B	179.8 (4)	C1E—C2E—C3E—C4E	0.1
C4B—C5B—C6B—C1B	−1.3 (7)	O21E—C2E—C3E—C4E	−178.7
C6B—C1B—C11B—C12B	8.8 (6)	C2E—C3E—C4E—C5E	0.0
C2B—C1B—C11B—C12B	−173.2 (4)	C3E—C4E—C5E—C6E	−0.5
C1B—C11B—C12B—C13B	−179.7 (3)	C4E—C5E—C6E—C1E	0.9
C11B—C12B—C13B—O12B	6.4 (6)	C2E—C1E—C6E—C5E	−0.7
C11B—C12B—C13B—O11B	−173.8 (3)	C11E—C1E—C6E—C5E	−169.2
C3B—C2B—O21B—C21B	−0.1 (5)	C2E—C1E—C11E—C12E	−176.1
C1B—C2B—O21B—C21B	178.0 (3)	C6E—C1E—C11E—C12E	−7.4
C22B—C21B—O21B—C2B	−177.7 (3)	C2E—C1E—C11E—C12D	−69.7
C6C—C1C—C2C—O21C	−180.0 (3)	C6E—C1E—C11E—C12D	99.1
C11C—C1C—C2C—O21C	−1.0 (4)	C13D—C12D—C11E—C1E	−7.3
C6C—C1C—C2C—C3C	−0.4 (5)	C11D—C12D—C11E—C1E	−124.2
C11C—C1C—C2C—C3C	178.6 (3)	C13D—C12D—C11E—C12E	116.2
O21C—C2C—C3C—C4C	179.5 (3)	C11D—C12D—C11E—C12E	−0.7
C1C—C2C—C3C—C4C	−0.1 (6)	C1E—C11E—C12E—C13E	−123.6
C2C—C3C—C4C—C5C	0.7 (6)	C12D—C11E—C12E—C13E	115.4
C3C—C4C—C5C—C6C	−0.9 (6)	C1E—C11E—C12E—C11D	121.7
C4C—C5C—C6C—C1C	0.5 (6)	C12D—C11E—C12E—C11D	0.7
C2C—C1C—C6C—C5C	0.2 (5)	C1D—C11D—C12E—C13E	4.5
C11C—C1C—C6C—C5C	−178.8 (3)	C12D—C11D—C12E—C13E	−118.3
C2C—C1C—C11C—C12C	−177.8 (3)	C1D—C11D—C12E—C11E	122.1
C6C—C1C—C11C—C12C	1.1 (5)	C12D—C11D—C12E—C11E	−0.7
C1C—C11C—C12C—C13C	178.9 (3)	C11E—C12E—C13E—O12E	−23.8
C11C—C12C—C13C—O12C	5.2 (5)	C11D—C12E—C13E—O12E	77.5
C11C—C12C—C13C—O11C	−176.2 (3)	C11E—C12E—C13E—O11E	165.0
C1C—C2C—O21C—C21C	175.8 (3)	C11D—C12E—C13E—O11E	−93.7
C3C—C2C—O21C—C21C	−3.8 (5)	C1E—C2E—O21E—C21E	165.9
C22C—C21C—O21C—C2C	−174.0 (3)	C3E—C2E—O21E—C21E	−15.2
C6D—C1D—C2D—O21D	179.8	C22E—C21E—O21E—C2E	−171.1
C11D—C1D—C2D—O21D	8.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11C—H1C···O12B^i	0.82	1.81	2.618 (4)	166
O11B—H1B···O12C^i	0.82	1.79	2.593 (4)	167
O12A—H1A···O11A^ii	0.82	1.77	2.578 (6)	170

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

(d6hlt_s) (E)-3-(2-Ethoxyphenyl)propenoic acid and trans-2,4-bis(2-ethoxyphenyl)-trans-1,3-cyclobutane-dicarboxylic acid

Crystal data

0.124(C22H24O6)·2.752(C11H12O3)	Z = 2
Mr = 576.62	F(000) = 612
Triclinic, P1	Dx = 1.283 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.6452 (13) Å	Cell parameters from 728 reflections
b = 10.8577 (17) Å	θ = 2.4–26.3°
c = 17.262 (3) Å	µ = 0.09 mm^−1
α = 92.470 (3)°	T = 173 K
β = 92.102 (3)°	Irregular, white
γ = 112.563 (3)°	0.38 × 0.33 × 0.24 mm
V = 1492.4 (4) Å^3

Data collection

Bruker SMART 1K diffractometer	3167 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 25.5°, θmin = 1.2°
phi and ω scans	h = −10→8
8177 measured reflections	k = −13→13
5500 independent reflections	l = −20→20

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0572P)^2 + 0.0749P] where P = (Fo^2 + 2Fc^2)/3
5500 reflections	(Δ/σ)max < 0.001
390 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Experimental. The following alerts are triggered when using the ACTA-C CIF validation software:

PLAT301_ALERT_3_B Main Residue Disorder ························. 40.00 Perc. PLAT432_ALERT_2_B Short Inter X···Y Contact C3C.. C4D.. 3.09 A ng. PLAT432_ALERT_2_B Short Inter X···Y Contact C4C.. C3D.. 3.07 A ng. PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ···.. 28 PLAT432_ALERT_2_C Short Inter X···Y Contact C3C.. C3D.. 3.18 A ng. —— Authors comment: The assymetric unit consists of a mixture of the monomer and dimer. The short contacts are most probably due to the dimer not being properly optimized for the crystal structure at this point. Coordinates for the dimer molecule at a higher conversion stage was used as a starting point for the refinement. The dimer was also refined isotropically as a rigid body. This is necessary as the dimer is only present in about 4–5% occupancy (4% dimer occupancy = 8% of monomer consumed).

PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ···. ? —— Authors commment: Our moiety formula is correct as it takes the occupancy of the dimer and monomer molecules into account.

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	Occ. (<1)
C1A	1.0162 (3)	0.0296 (2)	0.22157 (15)	0.0409 (7)	0.876 (2)
C2A	1.0094 (4)	0.0241 (3)	0.30238 (15)	0.0419 (7)	0.876 (2)
C3A	1.1499 (4)	0.0338 (3)	0.34793 (17)	0.0495 (8)	0.876 (2)
H3A	1.1454	0.0318	0.4028	0.059*	0.876 (2)
C4A	1.2960 (4)	0.0462 (3)	0.31332 (19)	0.0562 (8)	0.876 (2)
H4A	1.3916	0.0519	0.3445	0.067*	0.876 (2)
C5A	1.3042 (4)	0.0504 (3)	0.2336 (2)	0.0578 (8)	0.876 (2)
H5A	1.4053	0.0595	0.2100	0.069*	0.876 (2)
C6A	1.1662 (4)	0.0414 (3)	0.18871 (17)	0.0511 (8)	0.876 (2)
H6A	1.1725	0.0432	0.1339	0.061*	0.876 (2)
C11A	0.8669 (3)	0.0204 (2)	0.17418 (14)	0.0431 (7)	0.876 (2)
H11A	0.7711	0.0140	0.2016	0.052*	0.876 (2)
C12A	0.8511 (4)	0.0198 (2)	0.09700 (14)	0.0458 (7)	0.876 (2)
H12A	0.9449	0.0270	0.0678	0.055*	0.876 (2)
C13A	0.6963 (4)	0.0087 (2)	0.05566 (15)	0.0453 (7)	0.876 (2)
C21A	0.8459 (4)	0.0094 (3)	0.41466 (14)	0.0461 (7)	0.876 (2)
H21C	0.9338	0.0898	0.4412	0.055*	0.876 (2)
H21D	0.8592	−0.0708	0.4338	0.055*	0.876 (2)
C22A	0.6753 (4)	0.0064 (3)	0.43047 (16)	0.0522 (8)	0.876 (2)
H22D	0.6661	0.0886	0.4139	0.078*	0.876 (2)
H22E	0.6586	−0.0005	0.4862	0.078*	0.876 (2)
H22F	0.5897	−0.0709	0.4016	0.078*	0.876 (2)
O11A	0.6924 (2)	0.01017 (19)	−0.01746 (11)	0.0515 (6)	0.876 (2)
O12A	0.5693 (3)	−0.0032 (2)	0.09562 (12)	0.0584 (6)	0.876 (2)
H1A	0.4880	−0.0083	0.0657	0.088*	0.876 (2)
O21A	0.8599 (3)	0.0121 (2)	0.33185 (10)	0.0461 (5)	0.876 (2)
C1B	0.7885 (3)	0.3467 (2)	0.12841 (14)	0.0335 (6)	0.876 (2)
C2B	0.7885 (3)	0.3357 (2)	0.04688 (14)	0.0335 (6)	0.876 (2)
C3B	0.6507 (3)	0.3319 (3)	0.00137 (16)	0.0429 (7)	0.876 (2)
H3B	0.6512	0.3246	−0.0537	0.051*	0.876 (2)
C4B	0.5132 (4)	0.3388 (3)	0.03635 (18)	0.0509 (8)	0.876 (2)
H4B	0.4188	0.3355	0.0051	0.061*	0.876 (2)
C5B	0.5107 (4)	0.3504 (3)	0.11661 (19)	0.0505 (8)	0.876 (2)
H5B	0.4157	0.3555	0.1403	0.061*	0.876 (2)
C6B	0.6481 (3)	0.3544 (3)	0.16136 (15)	0.0417 (7)	0.876 (2)
H6B	0.6467	0.3626	0.2163	0.050*	0.876 (2)
C11B	0.9351 (3)	0.3525 (2)	0.17578 (13)	0.0362 (6)	0.876 (2)
H11B	1.0318	0.3591	0.1489	0.043*	0.876 (2)
C12B	0.9469 (3)	0.3493 (2)	0.25290 (13)	0.0408 (7)	0.876 (2)
H12B	0.8521	0.3422	0.2814	0.049*	0.876 (2)
C13B	1.1002 (4)	0.3566 (2)	0.29525 (14)	0.0403 (6)	0.876 (2)
C21B	0.9331 (3)	0.3141 (3)	−0.06611 (13)	0.0354 (6)	0.876 (2)
H21E	0.9263	0.3928	−0.0906	0.043*	0.876 (2)
H21F	0.8372	0.2333	−0.0871	0.043*	0.876 (2)
C22B	1.0954 (4)	0.3014 (3)	−0.08263 (15)	0.0448 (7)	0.876 (2)
H22G	1.1891	0.3847	−0.0654	0.067*	0.876 (2)
H22H	1.0987	0.2837	−0.1386	0.067*	0.876 (2)
H22I	1.1045	0.2275	−0.0548	0.067*	0.876 (2)
O11B	1.0898 (2)	0.34100 (19)	0.36854 (10)	0.0481 (5)	0.876 (2)
H1B	1.1827	0.3460	0.3880	0.072*	0.876 (2)
O12B	1.2329 (3)	0.3776 (2)	0.26032 (11)	0.0467 (5)	0.876 (2)
O21B	0.9293 (2)	0.32927 (19)	0.01674 (10)	0.0383 (5)	0.876 (2)
C1C	0.2212 (3)	0.6717 (2)	0.42538 (12)	0.0383 (5)
C2C	0.2336 (3)	0.6865 (2)	0.34524 (12)	0.0387 (5)
C3C	0.1000 (3)	0.6899 (2)	0.29955 (14)	0.0519 (6)
H3C	0.1096	0.7004	0.2454	0.062*
C4C	−0.0476 (3)	0.6779 (3)	0.33352 (15)	0.0573 (7)
H4C	−0.1396	0.6791	0.3022	0.069*
C5C	−0.0623 (3)	0.6642 (2)	0.41232 (15)	0.0536 (7)
H5C	−0.1636	0.6567	0.4352	0.064*
C6C	0.0706 (3)	0.6614 (2)	0.45758 (13)	0.0467 (6)
H6C	0.0600	0.6522	0.5118	0.056*
C11C	0.3617 (3)	0.66488 (19)	0.47177 (12)	0.0386 (5)
H11C	0.4601	0.6754	0.4454	0.046*
C12C	0.3664 (3)	0.6453 (2)	0.54770 (12)	0.0444 (6)
H12C	0.2711	0.6359	0.5762	0.053*
C13C	0.5136 (3)	0.6378 (2)	0.58787 (12)	0.0430 (6)
C21C	0.3994 (3)	0.7040 (2)	0.23407 (11)	0.0406 (6)
H21A	0.3936	0.7882	0.2171	0.049*
H21B	0.3084	0.6279	0.2057	0.049*
C22C	0.5668 (3)	0.6999 (2)	0.21845 (12)	0.0456 (6)
H22A	0.6551	0.7730	0.2491	0.068*
H22B	0.5862	0.7099	0.1631	0.068*
H22C	0.5686	0.6142	0.2330	0.068*
O11C	0.49716 (19)	0.61046 (16)	0.65985 (8)	0.0557 (5)
H1C	0.5869	0.6081	0.6787	0.084*
O12C	0.6474 (2)	0.65866 (16)	0.55414 (8)	0.0515 (4)
O21C	0.38280 (17)	0.69618 (15)	0.31622 (8)	0.0435 (4)
C1D	1.0226 (10)	0.0482 (7)	0.2390 (4)	0.0386 (17)*	0.124 (2)
C2D	1.0064 (12)	0.0102 (8)	0.3149 (4)	0.0386 (17)*	0.124 (2)
C3D	1.1339 (14)	−0.0175 (10)	0.3546 (5)	0.0386 (17)*	0.124 (2)
H3D	1.1208	−0.0458	0.4062	0.046*	0.124 (2)
C4D	1.2788 (14)	−0.0024 (12)	0.3171 (6)	0.0386 (17)*	0.124 (2)
H4D	1.3662	−0.0188	0.3439	0.046*	0.124 (2)
C5D	1.2986 (13)	0.0354 (12)	0.2424 (6)	0.0386 (17)*	0.124 (2)
H5D	1.3976	0.0438	0.2170	0.046*	0.124 (2)
C6D	1.1710 (11)	0.0613 (9)	0.2043 (5)	0.0386 (17)*	0.124 (2)
H6D	1.1853	0.0890	0.1526	0.046*	0.124 (2)
C11D	0.8902 (8)	0.0913 (5)	0.2057 (4)	0.0386 (17)*	0.124 (2)
H11D	0.7763	0.0248	0.2159	0.046*	0.124 (2)
C12D	0.8950 (8)	0.1272 (6)	0.1203 (3)	0.0386 (17)*	0.124 (2)
H12D	0.9967	0.1256	0.0952	0.046*	0.124 (2)
C13D	0.7324 (10)	0.0497 (7)	0.0709 (4)	0.0386 (17)*	0.124 (2)
C21D	0.8448 (16)	−0.0161 (12)	0.4273 (5)	0.0386 (17)*	0.124 (2)
H21G	0.9383	0.0568	0.4566	0.046*	0.124 (2)
H21H	0.8496	−0.1024	0.4404	0.046*	0.124 (2)
C22D	0.6783 (16)	−0.0116 (15)	0.4483 (5)	0.0386 (17)*	0.124 (2)
H22J	0.6655	−0.0219	0.5041	0.058*	0.124 (2)
H22K	0.5867	−0.0843	0.4191	0.058*	0.124 (2)
H22L	0.6750	0.0744	0.4352	0.058*	0.124 (2)
O11D	0.7562 (13)	0.0444 (9)	−0.0043 (4)	0.0386 (17)*	0.124 (2)
H11E	0.6641	0.0012	−0.0289	0.058*	0.124 (2)
O12D	0.5934 (9)	0.0114 (8)	0.0960 (5)	0.0386 (17)*	0.124 (2)
O21D	0.8584 (12)	−0.0007 (9)	0.3461 (4)	0.0386 (17)*	0.124 (2)
C1E	0.7828 (11)	0.3225 (7)	0.1120 (5)	0.0386 (17)*	0.124 (2)
C2E	0.7926 (13)	0.3444 (8)	0.0336 (5)	0.0386 (17)*	0.124 (2)
C3E	0.6643 (15)	0.3668 (11)	−0.0075 (6)	0.0386 (17)*	0.124 (2)
H3E	0.6712	0.3817	−0.0613	0.046*	0.124 (2)
C4E	0.5264 (15)	0.3669 (13)	0.0317 (7)	0.0386 (17)*	0.124 (2)
H4E	0.4388	0.3820	0.0041	0.046*	0.124 (2)
C5E	0.5146 (14)	0.3458 (13)	0.1091 (7)	0.0386 (17)*	0.124 (2)
H5E	0.4203	0.3468	0.1353	0.046*	0.124 (2)
C6E	0.6424 (12)	0.3228 (10)	0.1488 (5)	0.0386 (17)*	0.124 (2)
H6E	0.6338	0.3068	0.2025	0.046*	0.124 (2)
C11E	0.9126 (9)	0.2761 (6)	0.1467 (4)	0.0386 (17)*	0.124 (2)
H11F	1.0277	0.3412	0.1370	0.046*	0.124 (2)
C12E	0.9055 (9)	0.2403 (6)	0.2322 (4)	0.0386 (17)*	0.124 (2)
H12E	0.8023	0.2408	0.2562	0.046*	0.124 (2)
C13E	1.0645 (11)	0.3168 (7)	0.2831 (4)	0.0386 (17)*	0.124 (2)
C21E	0.9380 (16)	0.3355 (12)	−0.0822 (4)	0.0386 (17)*	0.124 (2)
H21I	0.9374	0.4185	−0.1035	0.046*	0.124 (2)
H21J	0.8374	0.2594	−0.1042	0.046*	0.124 (2)
C22E	1.0965 (16)	0.3150 (15)	−0.1027 (5)	0.0386 (17)*	0.124 (2)
H22M	1.1011	0.3084	−0.1593	0.058*	0.124 (2)
H22N	1.0954	0.2325	−0.0813	0.058*	0.124 (2)
H22O	1.1950	0.3910	−0.0806	0.058*	0.124 (2)
O11E	1.0396 (14)	0.3063 (9)	0.3571 (4)	0.0386 (17)*	0.124 (2)
H11G	1.1299	0.3497	0.3830	0.058*	0.124 (2)
O12E	1.2033 (10)	0.3675 (7)	0.2571 (5)	0.0386 (17)*	0.124 (2)
O21E	0.9371 (13)	0.3445 (9)	0.0012 (4)	0.0386 (17)*	0.124 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0517 (17)	0.0311 (14)	0.0388 (16)	0.0136 (13)	0.0141 (13)	0.0042 (11)
C2A	0.0439 (17)	0.0392 (15)	0.0404 (17)	0.0132 (13)	0.0096 (13)	0.0004 (12)
C3A	0.0512 (19)	0.0520 (19)	0.0458 (17)	0.0199 (16)	0.0086 (14)	0.0015 (14)
C4A	0.0473 (19)	0.054 (2)	0.068 (2)	0.0208 (16)	0.0072 (15)	0.0002 (16)
C5A	0.053 (2)	0.0555 (19)	0.069 (2)	0.0239 (16)	0.0231 (16)	0.0051 (16)
C6A	0.065 (2)	0.0455 (17)	0.0446 (18)	0.0222 (15)	0.0219 (15)	0.0031 (13)
C11A	0.0577 (18)	0.0315 (14)	0.0387 (16)	0.0146 (13)	0.0153 (13)	0.0028 (11)
C12A	0.0614 (19)	0.0382 (15)	0.0389 (16)	0.0193 (14)	0.0142 (13)	0.0051 (12)
C13A	0.065 (2)	0.0314 (15)	0.0370 (17)	0.0148 (14)	0.0128 (14)	0.0042 (12)
C21A	0.0558 (18)	0.0586 (19)	0.0285 (16)	0.0268 (15)	0.0062 (12)	0.0016 (12)
C22A	0.0528 (18)	0.069 (2)	0.0363 (17)	0.0246 (16)	0.0078 (13)	0.0028 (14)
O11A	0.0632 (14)	0.0536 (13)	0.0315 (11)	0.0145 (11)	0.0119 (9)	0.0058 (8)
O12A	0.0741 (15)	0.0621 (14)	0.0405 (12)	0.0258 (11)	0.0200 (11)	0.0091 (9)
O21A	0.0435 (11)	0.0631 (12)	0.0301 (11)	0.0187 (9)	0.0065 (8)	0.0013 (8)
C1B	0.0376 (15)	0.0333 (14)	0.0308 (14)	0.0146 (12)	0.0040 (11)	0.0036 (10)
C2B	0.0347 (15)	0.0327 (14)	0.0339 (15)	0.0134 (11)	0.0047 (11)	0.0035 (10)
C3B	0.0403 (16)	0.0552 (19)	0.0349 (15)	0.0209 (15)	−0.0031 (12)	0.0022 (12)
C4B	0.0364 (17)	0.067 (2)	0.0522 (19)	0.0226 (16)	0.0010 (13)	0.0041 (15)
C5B	0.0437 (17)	0.0582 (18)	0.0563 (19)	0.0261 (14)	0.0139 (14)	0.0036 (14)
C6B	0.0456 (17)	0.0462 (17)	0.0349 (15)	0.0188 (14)	0.0090 (12)	0.0033 (12)
C11B	0.0464 (16)	0.0321 (14)	0.0291 (14)	0.0136 (12)	0.0059 (11)	0.0044 (10)
C12B	0.0489 (17)	0.0446 (16)	0.0298 (15)	0.0188 (13)	0.0041 (12)	0.0022 (11)
C13B	0.0595 (19)	0.0349 (15)	0.0288 (14)	0.0202 (14)	0.0059 (13)	0.0043 (11)
C21B	0.0369 (15)	0.0435 (16)	0.0246 (14)	0.0140 (12)	0.0024 (10)	0.0017 (11)
C22B	0.0479 (17)	0.0572 (18)	0.0341 (16)	0.0249 (14)	0.0089 (13)	0.0044 (13)
O11B	0.0549 (14)	0.0664 (13)	0.0278 (10)	0.0282 (11)	0.0041 (8)	0.0055 (9)
O12B	0.0518 (13)	0.0585 (12)	0.0290 (10)	0.0190 (10)	0.0096 (9)	0.0092 (8)
O21B	0.0377 (10)	0.0567 (12)	0.0246 (10)	0.0226 (9)	0.0037 (8)	0.0023 (8)
C1C	0.0407 (14)	0.0386 (13)	0.0344 (13)	0.0136 (11)	0.0082 (10)	−0.0003 (10)
C2C	0.0339 (13)	0.0437 (14)	0.0367 (13)	0.0131 (11)	0.0045 (10)	−0.0010 (10)
C3C	0.0440 (15)	0.0720 (17)	0.0411 (14)	0.0241 (13)	0.0036 (11)	0.0029 (12)
C4C	0.0409 (15)	0.0758 (19)	0.0599 (18)	0.0278 (14)	0.0044 (12)	0.0022 (14)
C5C	0.0447 (16)	0.0603 (17)	0.0607 (17)	0.0243 (13)	0.0187 (13)	0.0053 (13)
C6C	0.0515 (16)	0.0478 (14)	0.0418 (14)	0.0189 (12)	0.0153 (12)	0.0049 (11)
C11C	0.0436 (14)	0.0365 (13)	0.0343 (13)	0.0136 (11)	0.0079 (10)	0.0021 (9)
C12C	0.0514 (15)	0.0490 (14)	0.0334 (13)	0.0189 (12)	0.0123 (11)	0.0060 (10)
C13C	0.0612 (17)	0.0415 (13)	0.0255 (12)	0.0190 (12)	0.0049 (11)	0.0016 (10)
C21C	0.0405 (14)	0.0543 (14)	0.0280 (12)	0.0190 (11)	0.0028 (9)	0.0048 (10)
C22C	0.0437 (14)	0.0591 (15)	0.0355 (13)	0.0207 (12)	0.0070 (10)	0.0048 (11)
O11C	0.0534 (11)	0.0795 (12)	0.0327 (9)	0.0229 (9)	0.0045 (7)	0.0121 (8)
O12C	0.0570 (11)	0.0668 (11)	0.0339 (9)	0.0264 (9)	0.0128 (8)	0.0037 (7)
O21C	0.0369 (9)	0.0689 (11)	0.0267 (8)	0.0227 (8)	0.0026 (6)	0.0021 (7)

Geometric parameters (Å, º)

C1A—C6A	1.397 (4)	C12C—C13C	1.458 (3)
C1A—C2A	1.401 (3)	C12C—H12C	0.9500
C1A—C11A	1.470 (4)	C13C—O12C	1.260 (3)
C2A—O21A	1.368 (3)	C13C—O11C	1.290 (2)
C2A—C3A	1.389 (4)	C21C—O21C	1.433 (2)
C3A—C4A	1.379 (4)	C21C—C22C	1.499 (3)
C3A—H3A	0.9500	C21C—H21A	0.9900
C4A—C5A	1.383 (4)	C21C—H21B	0.9900
C4A—H4A	0.9500	C22C—H22A	0.9800
C5A—C6A	1.366 (4)	C22C—H22B	0.9800
C5A—H5A	0.9500	C22C—H22C	0.9800
C6A—H6A	0.9500	O11C—H1C	0.8400
C11A—C12A	1.334 (3)	C1D—C2D	1.3866
C11A—H11A	0.9500	C1D—C6D	1.3961
C12A—C13A	1.454 (4)	C1D—C11D	1.4979
C12A—H12A	0.9500	C2D—O21D	1.3716
C13A—O11A	1.262 (3)	C2D—C3D	1.4116
C13A—O12A	1.285 (3)	C3D—C4D	1.3884
C21A—O21A	1.440 (3)	C3D—H3D	0.9500
C21A—C22A	1.497 (3)	C4D—C5D	1.3674
C21A—H21C	0.9900	C4D—H4D	0.9500
C21A—H21D	0.9900	C5D—C6D	1.3890
C22A—H22D	0.9800	C5D—H5D	0.9500
C22A—H22E	0.9800	C6D—H6D	0.9500
C22A—H22F	0.9800	C11D—C12D	1.5394
O12A—H1A	0.8400	C11D—C12E	1.6166
C1B—C6B	1.389 (3)	C11D—H11D	1.0000
C1B—C2B	1.407 (3)	C12D—C13D	1.5337
C1B—C11B	1.462 (3)	C12D—C11E	1.6084
C2B—O21B	1.366 (3)	C12D—H12D	1.0000
C2B—C3B	1.389 (3)	C13D—O12D	1.2148
C3B—C4B	1.379 (3)	C13D—O11D	1.3234
C3B—H3B	0.9500	C21D—O21D	1.4229
C4B—C5B	1.387 (4)	C21D—C22D	1.5151
C4B—H4B	0.9500	C21D—H21G	0.9900
C5B—C6B	1.378 (4)	C21D—H21H	0.9900
C5B—H5B	0.9500	C22D—H22J	0.9800
C6B—H6B	0.9500	C22D—H22K	0.9800
C11B—C12B	1.334 (3)	C22D—H22L	0.9800
C11B—H11B	0.9500	O11D—H11E	0.8400
C12B—C13B	1.463 (3)	C1E—C2E	1.3829
C12B—H12B	0.9500	C1E—C6E	1.3919
C13B—O12B	1.262 (3)	C1E—C11E	1.5118
C13B—O11B	1.285 (3)	C2E—O21E	1.3878
C21B—O21B	1.436 (3)	C2E—C3E	1.3985
C21B—C22B	1.497 (3)	C3E—C4E	1.3933
C21B—H21E	0.9900	C3E—H3E	0.9500
C21B—H21F	0.9900	C4E—C5E	1.3664
C22B—H22G	0.9800	C4E—H4E	0.9500
C22B—H22H	0.9800	C5E—C6E	1.3865
C22B—H22I	0.9800	C5E—H5E	0.9500
O11B—H1B	0.8400	C6E—H6E	0.9500
C1C—C6C	1.401 (3)	C11E—C12E	1.5393
C1C—C2C	1.403 (3)	C11E—H11F	1.0000
C1C—C11C	1.458 (3)	C12E—C13E	1.5245
C2C—O21C	1.369 (2)	C12E—H12E	1.0000
C2C—C3C	1.388 (3)	C13E—O12E	1.2245
C3C—C4C	1.387 (3)	C13E—O11E	1.3047
C3C—H3C	0.9500	C21E—O21E	1.4391
C4C—C5C	1.380 (3)	C21E—C22E	1.5213
C4C—H4C	0.9500	C21E—H21I	0.9900
C5C—C6C	1.377 (3)	C21E—H21J	0.9900
C5C—H5C	0.9500	C22E—H22M	0.9800
C6C—H6C	0.9500	C22E—H22N	0.9800
C11C—C12C	1.339 (3)	C22E—H22O	0.9800
C11C—H11C	0.9500	O11E—H11G	0.8400
C6A—C1A—C2A	118.0 (3)	O21C—C21C—C22C	106.68 (16)
C6A—C1A—C11A	122.2 (2)	O21C—C21C—H21A	110.4
C2A—C1A—C11A	119.7 (2)	C22C—C21C—H21A	110.4
O21A—C2A—C3A	123.7 (2)	O21C—C21C—H21B	110.4
O21A—C2A—C1A	115.9 (2)	C22C—C21C—H21B	110.4
C3A—C2A—C1A	120.4 (3)	H21A—C21C—H21B	108.6
C4A—C3A—C2A	119.8 (3)	C21C—C22C—H22A	109.5
C4A—C3A—H3A	120.1	C21C—C22C—H22B	109.5
C2A—C3A—H3A	120.1	H22A—C22C—H22B	109.5
C3A—C4A—C5A	120.5 (3)	C21C—C22C—H22C	109.5
C3A—C4A—H4A	119.8	H22A—C22C—H22C	109.5
C5A—C4A—H4A	119.8	H22B—C22C—H22C	109.5
C6A—C5A—C4A	119.8 (3)	C13C—O11C—H1C	109.5
C6A—C5A—H5A	120.1	C2C—O21C—C21C	118.45 (15)
C4A—C5A—H5A	120.1	C2D—C1D—C6D	117.6
C5A—C6A—C1A	121.5 (3)	C2D—C1D—C11D	116.5
C5A—C6A—H6A	119.2	C6D—C1D—C11D	125.3
C1A—C6A—H6A	119.2	O21D—C2D—C1D	115.0
C12A—C11A—C1A	127.2 (3)	O21D—C2D—C3D	124.0
C12A—C11A—H11A	116.4	C1D—C2D—C3D	121.0
C1A—C11A—H11A	116.4	C4D—C3D—C2D	118.8
C11A—C12A—C13A	122.7 (3)	C4D—C3D—H3D	120.6
C11A—C12A—H12A	118.6	C2D—C3D—H3D	120.6
C13A—C12A—H12A	118.6	C5D—C4D—C3D	121.6
O11A—C13A—O12A	123.2 (3)	C5D—C4D—H4D	119.2
O11A—C13A—C12A	118.7 (2)	C3D—C4D—H4D	119.2
O12A—C13A—C12A	118.1 (2)	C4D—C5D—C6D	118.6
O21A—C21A—C22A	107.1 (2)	C4D—C5D—H5D	120.7
O21A—C21A—H21C	110.3	C6D—C5D—H5D	120.7
C22A—C21A—H21C	110.3	C5D—C6D—C1D	122.5
O21A—C21A—H21D	110.3	C5D—C6D—H6D	118.7
C22A—C21A—H21D	110.3	C1D—C6D—H6D	118.7
H21C—C21A—H21D	108.6	C1D—C11D—C12D	119.2
C21A—C22A—H22D	109.5	C1D—C11D—C12E	116.5
C21A—C22A—H22E	109.5	C12D—C11D—C12E	89.6
H22D—C22A—H22E	109.5	C1D—C11D—H11D	110.0
C21A—C22A—H22F	109.5	C12D—C11D—H11D	110.0
H22D—C22A—H22F	109.5	C12E—C11D—H11D	110.0
H22E—C22A—H22F	109.5	C13D—C12D—C11D	114.6
C13A—O12A—H1A	109.5	C13D—C12D—C11E	112.4
C2A—O21A—C21A	118.73 (19)	C11D—C12D—C11E	90.4
C6B—C1B—C2B	118.1 (2)	C13D—C12D—H12D	112.6
C6B—C1B—C11B	122.0 (2)	C11D—C12D—H12D	112.6
C2B—C1B—C11B	119.9 (2)	C11E—C12D—H12D	112.6
O21B—C2B—C3B	123.3 (2)	O12D—C13D—O11D	122.4
O21B—C2B—C1B	116.3 (2)	O12D—C13D—C12D	124.0
C3B—C2B—C1B	120.4 (2)	O11D—C13D—C12D	113.0
C4B—C3B—C2B	119.7 (2)	O21D—C21D—C22D	107.7
C4B—C3B—H3B	120.1	O21D—C21D—H21G	110.2
C2B—C3B—H3B	120.1	C22D—C21D—H21G	110.2
C3B—C4B—C5B	120.9 (2)	O21D—C21D—H21H	110.2
C3B—C4B—H4B	119.5	C22D—C21D—H21H	110.2
C5B—C4B—H4B	119.5	H21G—C21D—H21H	108.5
C6B—C5B—C4B	119.0 (2)	C21D—C22D—H22J	109.5
C6B—C5B—H5B	120.5	C21D—C22D—H22K	109.5
C4B—C5B—H5B	120.5	H22J—C22D—H22K	109.5
C5B—C6B—C1B	121.9 (2)	C21D—C22D—H22L	109.5
C5B—C6B—H6B	119.1	H22J—C22D—H22L	109.5
C1B—C6B—H6B	119.1	H22K—C22D—H22L	109.5
C12B—C11B—C1B	126.5 (2)	C13D—O11D—H11E	109.5
C12B—C11B—H11B	116.7	C2D—O21D—C21D	118.0
C1B—C11B—H11B	116.7	C2E—C1E—C6E	118.5
C11B—C12B—C13B	122.5 (2)	C2E—C1E—C11E	115.6
C11B—C12B—H12B	118.8	C6E—C1E—C11E	124.9
C13B—C12B—H12B	118.8	C1E—C2E—O21E	115.2
O12B—C13B—O11B	123.4 (2)	C1E—C2E—C3E	120.7
O12B—C13B—C12B	120.6 (2)	O21E—C2E—C3E	124.1
O11B—C13B—C12B	115.9 (2)	C4E—C3E—C2E	119.0
O21B—C21B—C22B	107.09 (18)	C4E—C3E—H3E	120.5
O21B—C21B—H21E	110.3	C2E—C3E—H3E	120.5
C22B—C21B—H21E	110.3	C5E—C4E—C3E	121.3
O21B—C21B—H21F	110.3	C5E—C4E—H4E	119.4
C22B—C21B—H21F	110.3	C3E—C4E—H4E	119.4
H21E—C21B—H21F	108.6	C4E—C5E—C6E	119.0
C21B—C22B—H22G	109.5	C4E—C5E—H5E	120.5
C21B—C22B—H22H	109.5	C6E—C5E—H5E	120.5
H22G—C22B—H22H	109.5	C5E—C6E—C1E	121.6
C21B—C22B—H22I	109.5	C5E—C6E—H6E	119.2
H22G—C22B—H22I	109.5	C1E—C6E—H6E	119.2
H22H—C22B—H22I	109.5	C1E—C11E—C12E	119.6
C13B—O11B—H1B	109.5	C1E—C11E—C12D	116.7
C2B—O21B—C21B	118.34 (17)	C12E—C11E—C12D	89.9
C6C—C1C—C2C	117.9 (2)	C1E—C11E—H11F	109.7
C6C—C1C—C11C	122.4 (2)	C12E—C11E—H11F	109.7
C2C—C1C—C11C	119.69 (19)	C12D—C11E—H11F	109.7
O21C—C2C—C3C	123.3 (2)	C13E—C12E—C11E	115.4
O21C—C2C—C1C	115.99 (18)	C13E—C12E—C11D	112.1
C3C—C2C—C1C	120.8 (2)	C11E—C12E—C11D	90.1
C2C—C3C—C4C	119.6 (2)	C13E—C12E—H12E	112.5
C2C—C3C—H3C	120.2	C11E—C12E—H12E	112.5
C4C—C3C—H3C	120.2	C11D—C12E—H12E	112.5
C5C—C4C—C3C	120.7 (2)	O12E—C13E—O11E	123.8
C5C—C4C—H4C	119.6	O12E—C13E—C12E	123.0
C3C—C4C—H4C	119.6	O11E—C13E—C12E	112.5
C6C—C5C—C4C	119.6 (2)	O21E—C21E—C22E	107.3
C6C—C5C—H5C	120.2	O21E—C21E—H21I	110.3
C4C—C5C—H5C	120.2	C22E—C21E—H21I	110.3
C5C—C6C—C1C	121.4 (2)	O21E—C21E—H21J	110.3
C5C—C6C—H6C	119.3	C22E—C21E—H21J	110.3
C1C—C6C—H6C	119.3	H21I—C21E—H21J	108.5
C12C—C11C—C1C	126.7 (2)	C21E—C22E—H22M	109.5
C12C—C11C—H11C	116.6	C21E—C22E—H22N	109.5
C1C—C11C—H11C	116.6	H22M—C22E—H22N	109.5
C11C—C12C—C13C	121.9 (2)	C21E—C22E—H22O	109.5
C11C—C12C—H12C	119.0	H22M—C22E—H22O	109.5
C13C—C12C—H12C	119.0	H22N—C22E—H22O	109.5
O12C—C13C—O11C	123.0 (2)	C13E—O11E—H11G	109.5
O12C—C13C—C12C	121.7 (2)	C2E—O21E—C21E	117.6
O11C—C13C—C12C	115.3 (2)
C6A—C1A—C2A—O21A	−179.7 (2)	C6D—C1D—C2D—C3D	−1.6
C11A—C1A—C2A—O21A	−1.0 (3)	C11D—C1D—C2D—C3D	−172.7
C6A—C1A—C2A—C3A	1.7 (4)	O21D—C2D—C3D—C4D	−179.8
C11A—C1A—C2A—C3A	−179.5 (2)	C1D—C2D—C3D—C4D	1.7
O21A—C2A—C3A—C4A	−179.7 (2)	C2D—C3D—C4D—C5D	−1.5
C1A—C2A—C3A—C4A	−1.3 (4)	C3D—C4D—C5D—C6D	1.1
C2A—C3A—C4A—C5A	0.6 (4)	C4D—C5D—C6D—C1D	−1.0
C3A—C4A—C5A—C6A	−0.4 (4)	C2D—C1D—C6D—C5D	1.3
C4A—C5A—C6A—C1A	0.8 (4)	C11D—C1D—C6D—C5D	171.5
C2A—C1A—C6A—C5A	−1.5 (4)	C2D—C1D—C11D—C12D	−176.6
C11A—C1A—C6A—C5A	179.8 (2)	C6D—C1D—C11D—C12D	13.1
C6A—C1A—C11A—C12A	1.0 (4)	C2D—C1D—C11D—C12E	77.8
C2A—C1A—C11A—C12A	−177.8 (2)	C6D—C1D—C11D—C12E	−92.6
C1A—C11A—C12A—C13A	179.3 (2)	C1D—C11D—C12D—C13D	125.2
C11A—C12A—C13A—O11A	179.4 (2)	C12E—C11D—C12D—C13D	−114.3
C11A—C12A—C13A—O12A	−1.2 (4)	C1D—C11D—C12D—C11E	−119.8
C3A—C2A—O21A—C21A	0.1 (4)	C12E—C11D—C12D—C11E	0.7
C1A—C2A—O21A—C21A	−178.4 (2)	C11D—C12D—C13D—O12D	31.8
C22A—C21A—O21A—C2A	175.7 (2)	C11E—C12D—C13D—O12D	−69.5
C6B—C1B—C2B—O21B	179.6 (2)	C11D—C12D—C13D—O11D	−157.0
C11B—C1B—C2B—O21B	0.8 (3)	C11E—C12D—C13D—O11D	101.6
C6B—C1B—C2B—C3B	−0.4 (3)	C1D—C2D—O21D—C21D	−169.1
C11B—C1B—C2B—C3B	−179.2 (2)	C3D—C2D—O21D—C21D	12.3
O21B—C2B—C3B—C4B	179.9 (2)	C22D—C21D—O21D—C2D	174.3
C1B—C2B—C3B—C4B	−0.1 (4)	C6E—C1E—C2E—O21E	179.2
C2B—C3B—C4B—C5B	0.5 (4)	C11E—C1E—C2E—O21E	−11.3
C3B—C4B—C5B—C6B	−0.3 (4)	C6E—C1E—C2E—C3E	0.2
C4B—C5B—C6B—C1B	−0.2 (4)	C11E—C1E—C2E—C3E	169.8
C2B—C1B—C6B—C5B	0.6 (4)	C1E—C2E—C3E—C4E	0.1
C11B—C1B—C6B—C5B	179.3 (2)	O21E—C2E—C3E—C4E	−178.7
C6B—C1B—C11B—C12B	8.5 (4)	C2E—C3E—C4E—C5E	0.0
C2B—C1B—C11B—C12B	−172.8 (2)	C3E—C4E—C5E—C6E	−0.5
C1B—C11B—C12B—C13B	−179.6 (2)	C4E—C5E—C6E—C1E	0.9
C11B—C12B—C13B—O12B	6.0 (4)	C2E—C1E—C6E—C5E	−0.7
C11B—C12B—C13B—O11B	−174.2 (2)	C11E—C1E—C6E—C5E	−169.2
C3B—C2B—O21B—C21B	−1.8 (3)	C2E—C1E—C11E—C12E	−176.1
C1B—C2B—O21B—C21B	178.21 (19)	C6E—C1E—C11E—C12E	−7.4
C22B—C21B—O21B—C2B	−176.56 (19)	C2E—C1E—C11E—C12D	−69.7
C6C—C1C—C2C—O21C	−179.96 (19)	C6E—C1E—C11E—C12D	99.1
C11C—C1C—C2C—O21C	−1.2 (3)	C13D—C12D—C11E—C1E	−7.3
C6C—C1C—C2C—C3C	−0.4 (3)	C11D—C12D—C11E—C1E	−124.2
C11C—C1C—C2C—C3C	178.4 (2)	C13D—C12D—C11E—C12E	116.2
O21C—C2C—C3C—C4C	179.3 (2)	C11D—C12D—C11E—C12E	−0.7
C1C—C2C—C3C—C4C	−0.3 (3)	C1E—C11E—C12E—C13E	−123.6
C2C—C3C—C4C—C5C	0.7 (4)	C12D—C11E—C12E—C13E	115.4
C3C—C4C—C5C—C6C	−0.5 (4)	C1E—C11E—C12E—C11D	121.7
C4C—C5C—C6C—C1C	−0.2 (4)	C12D—C11E—C12E—C11D	0.7
C2C—C1C—C6C—C5C	0.6 (3)	C1D—C11D—C12E—C13E	4.5
C11C—C1C—C6C—C5C	−178.1 (2)	C12D—C11D—C12E—C13E	−118.3
C6C—C1C—C11C—C12C	1.7 (3)	C1D—C11D—C12E—C11E	122.1
C2C—C1C—C11C—C12C	−176.9 (2)	C12D—C11D—C12E—C11E	−0.7
C1C—C11C—C12C—C13C	178.88 (19)	C11E—C12E—C13E—O12E	−23.8
C11C—C12C—C13C—O12C	4.9 (3)	C11D—C12E—C13E—O12E	77.5
C11C—C12C—C13C—O11C	−175.92 (19)	C11E—C12E—C13E—O11E	165.0
C3C—C2C—O21C—C21C	−3.0 (3)	C11D—C12E—C13E—O11E	−93.7
C1C—C2C—O21C—C21C	176.63 (17)	C1E—C2E—O21E—C21E	165.9
C22C—C21C—O21C—C2C	−174.50 (18)	C3E—C2E—O21E—C21E	−15.2
C6D—C1D—C2D—O21D	179.8	C22E—C21E—O21E—C2E	−171.1
C11D—C1D—C2D—O21D	8.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12A—H1A···O11A^i	0.84	1.73	2.566 (3)	170
O11B—H1B···O12C^ii	0.84	1.76	2.591 (2)	168
O11C—H1C···O12B^ii	0.84	1.80	2.622 (3)	166

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