5,7-Bis(benz­yloxy)-4H-benzopyran-4-one

The title compound, C₂₃H₁₈O₄, contains two mol­ecules in the asymmetric unit which differ from each other in the dihedral angles between the benzyl and chromone groups. There are intra­molecular and inter­molecular C—H...O inter­actions as well as π–π stacking inter­actions in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.141
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

5,7-bis(benzyloxy)-4H-benzopyran-4-one

Crystal data

C23H18O4	Z = 4
Mr = 358.37	F(000) = 752
Triclinic, P1	Dx = 1.297 Mg m^−3
Hall symbol: -P 1	Melting point: 423.2 K
a = 9.251 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.493 (2) Å	Cell parameters from 2940 reflections
c = 14.785 (2) Å	θ = 2.6–25.8°
α = 92.881 (2)°	µ = 0.09 mm^−1
β = 95.480 (2)°	T = 293 K
γ = 90.096 (2)°	Block, colorless
V = 1834.8 (4) Å^3	0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART Apex CCD area-detector diffractometer	6337 independent reflections
Radiation source: fine-focus sealed tube	4578 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→10
Tmin = 0.97, Tmax = 0.98	k = −16→13
9179 measured reflections	l = −16→17

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0748P)^2 + 0.255P] where P = (Fo^2 + 2Fc^2)/3
6337 reflections	(Δ/σ)max < 0.001
487 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.0581 (3)	1.26419 (17)	0.05385 (17)	0.0500 (6)
H1	−0.1138	1.3141	0.0785	0.060*
C2	−0.0473 (3)	1.26131 (17)	−0.03357 (17)	0.0499 (6)
H2	−0.0977	1.3079	−0.0684	0.060*
C3	0.0395 (2)	1.18906 (17)	−0.07842 (16)	0.0454 (5)
C4	0.1100 (2)	1.11601 (16)	−0.01759 (15)	0.0420 (5)
C5	0.1975 (2)	1.03559 (15)	−0.04395 (15)	0.0411 (5)
C6	0.2595 (2)	0.97263 (16)	0.01739 (15)	0.0410 (5)
H6	0.3174	0.9209	−0.0018	0.049*
C7	0.2360 (2)	0.98582 (16)	0.10893 (15)	0.0430 (5)
C8	0.1544 (2)	1.06419 (16)	0.13942 (16)	0.0434 (5)
H8	0.1422	1.0752	0.2008	0.052*
C9	0.0917 (2)	1.12539 (16)	0.07489 (15)	0.0429 (5)
C10	0.2939 (3)	0.94700 (17)	−0.16984 (15)	0.0464 (5)
H10A	0.2573	0.8843	−0.1519	0.056*
H10B	0.3957	0.9531	−0.1474	0.056*
C11	0.2757 (3)	0.95195 (17)	−0.27061 (16)	0.0474 (5)
C12	0.1884 (3)	1.02277 (18)	−0.31407 (17)	0.0514 (6)
H12	0.1391	1.0690	−0.2799	0.062*
C13	0.1749 (3)	1.02443 (19)	−0.40865 (16)	0.0518 (6)
H13	0.1168	1.0720	−0.4373	0.062*
C14	0.2461 (3)	0.95710 (19)	−0.45939 (17)	0.0525 (6)
H14	0.2368	0.9583	−0.5225	0.063*
C15	0.3332 (3)	0.88633 (19)	−0.41564 (17)	0.0531 (6)
H15	0.3831	0.8407	−0.4500	0.064*
C16	0.3463 (3)	0.88297 (18)	−0.32285 (16)	0.0506 (6)
H16	0.4029	0.8342	−0.2948	0.061*
C17	0.2697 (3)	0.92815 (18)	0.25860 (15)	0.0468 (5)
H17A	0.1658	0.9305	0.2628	0.056*
H17B	0.3133	0.9886	0.2875	0.056*
C18	0.3340 (3)	0.83856 (17)	0.30443 (15)	0.0466 (5)
C19	0.4828 (3)	0.83063 (18)	0.32802 (16)	0.0508 (6)
H19	0.5461	0.8791	0.3122	0.061*
C20	0.5362 (3)	0.74995 (18)	0.37522 (16)	0.0517 (6)
H20	0.6353	0.7450	0.3920	0.062*
C21	0.4417 (3)	0.67658 (18)	0.39740 (16)	0.0512 (6)
H21	0.4779	0.6218	0.4277	0.061*
C22	0.2938 (3)	0.68516 (18)	0.37432 (16)	0.0516 (6)
H22	0.2304	0.6368	0.3903	0.062*
C23	0.2399 (3)	0.76603 (18)	0.32725 (16)	0.0501 (6)
H23	0.1407	0.7714	0.3111	0.060*
C1'	0.5705 (3)	0.76848 (18)	0.07014 (18)	0.0522 (6)
H1'	0.6293	0.8192	0.0984	0.063*
C2'	0.5432 (3)	0.76731 (17)	−0.01890 (18)	0.0499 (6)
H2'	0.5884	0.8141	−0.0510	0.060*
C3'	0.4447 (2)	0.69525 (16)	−0.06870 (17)	0.0455 (5)
C4'	0.3887 (2)	0.62048 (16)	−0.01010 (16)	0.0453 (5)
C5'	0.2967 (2)	0.54123 (16)	−0.04290 (16)	0.0451 (5)
C6'	0.2483 (2)	0.47515 (17)	0.01711 (16)	0.0463 (5)
H6'	0.1866	0.4231	−0.0049	0.056*
C7'	0.2912 (3)	0.48644 (17)	0.10869 (17)	0.0483 (6)
C8'	0.3817 (3)	0.56351 (17)	0.14392 (17)	0.0488 (6)
H8'	0.4102	0.5716	0.2059	0.059*
C9'	0.4281 (3)	0.62851 (16)	0.08214 (16)	0.0462 (5)
C10'	0.1820 (3)	0.44947 (18)	−0.17246 (16)	0.0500 (6)
H10C	0.0828	0.4507	−0.1564	0.060*
H10D	0.2276	0.3894	−0.1507	0.060*
C11'	0.1838 (3)	0.45163 (18)	−0.27329 (17)	0.0505 (6)
C12'	0.2542 (3)	0.52625 (18)	−0.31296 (17)	0.0504 (6)
H12'	0.3021	0.5766	−0.2765	0.060*
C13'	0.2540 (3)	0.52646 (19)	−0.40722 (17)	0.0536 (6)
H13'	0.3039	0.5753	−0.4340	0.064*
C14'	0.1785 (3)	0.45289 (19)	−0.46000 (18)	0.0533 (6)
H14'	0.1759	0.4526	−0.5230	0.064*
C15'	0.1070 (3)	0.37990 (18)	−0.41999 (17)	0.0526 (6)
H15'	0.0553	0.3314	−0.4566	0.063*
C16'	0.1101 (3)	0.37701 (18)	−0.32751 (16)	0.0518 (6)
H16'	0.0637	0.3260	−0.3013	0.062*
C17'	0.2906 (3)	0.42000 (19)	0.25486 (17)	0.0522 (6)
H17C	0.2649	0.4825	0.2843	0.063*
H17D	0.3955	0.4138	0.2620	0.063*
C18'	0.2216 (3)	0.33567 (18)	0.29664 (17)	0.0500 (6)
C19'	0.3084 (3)	0.26727 (19)	0.34161 (18)	0.0560 (6)
H19'	0.4090	0.2712	0.3438	0.067*
C20'	0.2409 (3)	0.1921 (2)	0.38376 (18)	0.0569 (6)
H20'	0.2978	0.1456	0.4149	0.068*
C21'	0.0942 (3)	0.18515 (19)	0.38041 (17)	0.0540 (6)
H21'	0.0516	0.1333	0.4077	0.065*
C22'	0.0103 (3)	0.25323 (19)	0.33769 (17)	0.0554 (6)
H22'	−0.0902	0.2483	0.3360	0.066*
C23'	0.0722 (3)	0.33096 (19)	0.29604 (17)	0.0534 (6)
H23'	0.0140	0.3790	0.2682	0.064*
O1	0.00772 (17)	1.19819 (11)	0.11100 (11)	0.0479 (4)
O2	0.05588 (17)	1.19208 (12)	−0.15917 (11)	0.0510 (4)
O3	0.21337 (17)	1.02751 (11)	−0.13400 (10)	0.0437 (4)
O4	0.30011 (17)	0.91831 (11)	0.16402 (10)	0.0456 (4)
O1'	0.51889 (17)	0.70133 (12)	0.12266 (11)	0.0514 (4)
O2'	0.41105 (18)	0.70030 (13)	−0.14952 (12)	0.0561 (4)
O3'	0.25970 (17)	0.53455 (11)	−0.13217 (10)	0.0477 (4)
O4'	0.23893 (18)	0.41731 (12)	0.15978 (11)	0.0513 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0504 (13)	0.0442 (13)	0.0554 (15)	0.0100 (10)	0.0045 (11)	0.0034 (11)
C2	0.0478 (13)	0.0433 (13)	0.0586 (16)	0.0083 (10)	0.0034 (11)	0.0055 (11)
C3	0.0462 (13)	0.0429 (12)	0.0476 (14)	0.0056 (10)	0.0045 (10)	0.0067 (10)
C4	0.0440 (12)	0.0379 (11)	0.0445 (13)	0.0057 (9)	0.0051 (9)	0.0042 (9)
C5	0.0452 (12)	0.0354 (11)	0.0440 (13)	0.0035 (9)	0.0080 (10)	0.0083 (9)
C6	0.0472 (12)	0.0353 (11)	0.0422 (12)	0.0071 (9)	0.0107 (10)	0.0056 (9)
C7	0.0460 (12)	0.0411 (12)	0.0435 (13)	0.0065 (10)	0.0080 (10)	0.0096 (10)
C8	0.0459 (12)	0.0409 (12)	0.0441 (13)	0.0082 (10)	0.0068 (10)	0.0043 (10)
C9	0.0451 (12)	0.0372 (11)	0.0468 (13)	0.0070 (9)	0.0073 (10)	0.0024 (9)
C10	0.0529 (13)	0.0454 (13)	0.0431 (13)	0.0077 (10)	0.0137 (10)	0.0078 (10)
C11	0.0502 (13)	0.0483 (13)	0.0464 (13)	0.0025 (10)	0.0166 (10)	0.0068 (10)
C12	0.0546 (14)	0.0518 (14)	0.0498 (14)	0.0024 (11)	0.0135 (11)	0.0073 (11)
C13	0.0552 (14)	0.0569 (15)	0.0454 (14)	0.0059 (11)	0.0140 (11)	0.0056 (11)
C14	0.0554 (14)	0.0569 (15)	0.0472 (14)	0.0076 (11)	0.0141 (11)	0.0045 (11)
C15	0.0535 (14)	0.0564 (15)	0.0516 (15)	0.0089 (11)	0.0178 (11)	0.0007 (11)
C16	0.0579 (14)	0.0483 (13)	0.0485 (14)	0.0093 (11)	0.0196 (11)	0.0030 (11)
C17	0.0532 (14)	0.0482 (13)	0.0408 (12)	0.0129 (11)	0.0070 (10)	0.0132 (10)
C18	0.0514 (13)	0.0490 (13)	0.0406 (13)	0.0074 (11)	0.0067 (10)	0.0102 (10)
C19	0.0527 (14)	0.0527 (14)	0.0479 (14)	0.0092 (11)	0.0037 (11)	0.0140 (11)
C20	0.0535 (14)	0.0568 (15)	0.0460 (14)	0.0121 (11)	0.0043 (11)	0.0141 (11)
C21	0.0562 (14)	0.0526 (14)	0.0459 (13)	0.0137 (11)	0.0047 (11)	0.0131 (11)
C22	0.0558 (14)	0.0527 (14)	0.0480 (14)	0.0089 (11)	0.0072 (11)	0.0151 (11)
C23	0.0540 (14)	0.0507 (14)	0.0471 (13)	0.0057 (11)	0.0057 (11)	0.0150 (11)
C1'	0.0527 (14)	0.0417 (13)	0.0625 (17)	−0.0069 (10)	0.0064 (12)	0.0047 (11)
C2'	0.0469 (13)	0.0442 (13)	0.0600 (16)	−0.0059 (10)	0.0088 (11)	0.0096 (11)
C3'	0.0442 (12)	0.0394 (12)	0.0544 (15)	−0.0032 (9)	0.0091 (11)	0.0090 (10)
C4'	0.0429 (12)	0.0402 (12)	0.0539 (14)	−0.0024 (9)	0.0079 (10)	0.0070 (10)
C5'	0.0465 (13)	0.0405 (12)	0.0494 (14)	−0.0030 (10)	0.0066 (10)	0.0092 (10)
C6'	0.0470 (13)	0.0414 (12)	0.0510 (14)	−0.0064 (10)	0.0051 (10)	0.0064 (10)
C7'	0.0517 (13)	0.0437 (13)	0.0506 (14)	−0.0045 (10)	0.0082 (11)	0.0082 (10)
C8'	0.0536 (14)	0.0423 (13)	0.0513 (14)	−0.0044 (10)	0.0086 (11)	0.0053 (10)
C9'	0.0516 (13)	0.0373 (12)	0.0506 (14)	−0.0058 (10)	0.0079 (11)	0.0049 (10)
C10'	0.0523 (14)	0.0464 (13)	0.0504 (14)	−0.0029 (11)	−0.0003 (11)	0.0042 (11)
C11'	0.0494 (13)	0.0505 (14)	0.0506 (14)	0.0073 (11)	0.0002 (11)	0.0017 (11)
C12'	0.0515 (14)	0.0519 (14)	0.0482 (14)	0.0117 (11)	0.0047 (11)	0.0075 (11)
C13'	0.0534 (14)	0.0572 (15)	0.0502 (15)	0.0141 (12)	0.0058 (11)	0.0021 (12)
C14'	0.0528 (14)	0.0545 (15)	0.0517 (15)	0.0177 (12)	0.0001 (11)	0.0008 (12)
C15'	0.0555 (14)	0.0498 (14)	0.0499 (15)	0.0163 (11)	−0.0043 (11)	−0.0061 (11)
C16'	0.0528 (14)	0.0505 (14)	0.0497 (15)	0.0106 (11)	−0.0033 (11)	−0.0050 (11)
C17'	0.0548 (14)	0.0511 (14)	0.0523 (15)	−0.0124 (11)	0.0102 (11)	0.0103 (11)
C18'	0.0523 (14)	0.0492 (13)	0.0502 (14)	−0.0060 (11)	0.0112 (11)	0.0062 (11)
C19'	0.0539 (14)	0.0564 (15)	0.0595 (16)	−0.0027 (12)	0.0101 (12)	0.0105 (12)
C20'	0.0579 (16)	0.0539 (15)	0.0601 (16)	−0.0039 (12)	0.0099 (12)	0.0085 (12)
C21'	0.0575 (15)	0.0525 (14)	0.0545 (15)	−0.0092 (12)	0.0155 (12)	0.0091 (11)
C22'	0.0556 (15)	0.0581 (15)	0.0549 (15)	−0.0102 (12)	0.0152 (12)	0.0100 (12)
C23'	0.0545 (14)	0.0550 (15)	0.0527 (15)	−0.0068 (11)	0.0118 (11)	0.0094 (11)
O1	0.0526 (9)	0.0421 (8)	0.0492 (9)	0.0134 (7)	0.0066 (7)	0.0020 (7)
O2	0.0489 (9)	0.0530 (10)	0.0530 (11)	0.0216 (7)	0.0084 (7)	0.0152 (8)
O3	0.0528 (9)	0.0391 (8)	0.0414 (9)	0.0072 (7)	0.0121 (7)	0.0072 (7)
O4	0.0522 (9)	0.0441 (9)	0.0419 (9)	0.0101 (7)	0.0070 (7)	0.0120 (7)
O1'	0.0527 (9)	0.0432 (9)	0.0586 (10)	−0.0093 (7)	0.0058 (8)	0.0045 (8)
O2'	0.0549 (10)	0.0549 (10)	0.0606 (11)	−0.0143 (8)	0.0075 (8)	0.0212 (8)
O3'	0.0541 (9)	0.0422 (9)	0.0470 (10)	−0.0042 (7)	0.0028 (7)	0.0072 (7)
O4'	0.0567 (10)	0.0486 (9)	0.0497 (10)	−0.0089 (7)	0.0064 (8)	0.0107 (7)

Geometric parameters (Å, º)

C1—C2	1.304 (3)	C1'—C2'	1.316 (3)
C1—O1	1.363 (3)	C1'—O1'	1.339 (3)
C1—H1	0.930	C1'—H1'	0.930
C2—C3	1.440 (3)	C2'—C3'	1.454 (3)
C2—H2	0.930	C2'—H2'	0.930
C3—O2	1.220 (3)	C3'—O2'	1.211 (3)
C3—C4	1.478 (3)	C3'—C4'	1.486 (3)
C4—C9	1.393 (3)	C4'—C9'	1.376 (3)
C4—C5	1.416 (3)	C4'—C5'	1.403 (3)
C5—O3	1.352 (3)	C5'—O3'	1.330 (3)
C5—C6	1.361 (3)	C5'—C6'	1.392 (3)
C6—C7	1.394 (3)	C6'—C7'	1.375 (3)
C6—H6	0.930	C6'—H6'	0.930
C7—O4	1.352 (3)	C7'—O4'	1.347 (3)
C7—C8	1.383 (3)	C7'—C8'	1.383 (3)
C8—C9	1.380 (3)	C8'—C9'	1.393 (3)
C8—H8	0.930	C8'—H8'	0.930
C9—O1	1.372 (3)	C9'—O1'	1.368 (3)
C10—O3	1.427 (3)	C10'—O3'	1.427 (3)
C10—C11	1.488 (3)	C10'—C11'	1.494 (3)
C10—H10A	0.970	C10'—H10C	0.970
C10—H10B	0.970	C10'—H10D	0.970
C11—C16	1.384 (3)	C11'—C12'	1.383 (3)
C11—C12	1.394 (3)	C11'—C16'	1.391 (3)
C12—C13	1.393 (3)	C12'—C13'	1.394 (3)
C12—H12	0.930	C12'—H12'	0.930
C13—C14	1.360 (3)	C13'—C14'	1.378 (4)
C13—H13	0.930	C13'—H13'	0.930
C14—C15	1.394 (4)	C14'—C15'	1.374 (4)
C14—H14	0.930	C14'—H14'	0.930
C15—C16	1.369 (3)	C15'—C16'	1.367 (3)
C15—H15	0.930	C15'—H15'	0.930
C16—H16	0.930	C16'—H16'	0.930
C17—O4	1.452 (3)	C17'—O4'	1.440 (3)
C17—C18	1.511 (3)	C17'—C18'	1.492 (3)
C17—H17A	0.970	C17'—H17C	0.970
C17—H17B	0.970	C17'—H17D	0.970
C18—C23	1.384 (3)	C18'—C19'	1.379 (4)
C18—C19	1.393 (3)	C18'—C23'	1.382 (3)
C19—C20	1.389 (3)	C19'—C20'	1.394 (3)
C19—H19	0.930	C19'—H19'	0.930
C20—C21	1.391 (4)	C20'—C21'	1.356 (4)
C20—H20	0.930	C20'—H20'	0.930
C21—C22	1.385 (3)	C21'—C22'	1.346 (4)
C21—H21	0.930	C21'—H21'	0.930
C22—C23	1.391 (3)	C22'—C23'	1.392 (3)
C22—H22	0.930	C22'—H22'	0.930
C23—H23	0.930	C23'—H23'	0.930
C2—C1—O1	123.7 (2)	C1'—C2'—C3'	122.1 (2)
C2—C1—H1	118.2	C1'—C2'—H2'	119.0
O1—C1—H1	118.2	C3'—C2'—H2'	119.0
C1—C2—C3	122.8 (2)	O2'—C3'—C2'	121.3 (2)
C1—C2—H2	118.6	O2'—C3'—C4'	125.3 (2)
C3—C2—H2	118.6	C2'—C3'—C4'	113.4 (2)
O2—C3—C2	121.5 (2)	C9'—C4'—C5'	117.2 (2)
O2—C3—C4	124.2 (2)	C9'—C4'—C3'	118.8 (2)
C2—C3—C4	114.2 (2)	C5'—C4'—C3'	124.0 (2)
C9—C4—C5	115.29 (19)	O3'—C5'—C6'	123.5 (2)
C9—C4—C3	118.57 (19)	O3'—C5'—C4'	116.4 (2)
C5—C4—C3	126.1 (2)	C6'—C5'—C4'	120.1 (2)
O3—C5—C6	123.72 (19)	C7'—C6'—C5'	120.3 (2)
O3—C5—C4	114.37 (18)	C7'—C6'—H6'	119.8
C6—C5—C4	121.9 (2)	C5'—C6'—H6'	119.8
C5—C6—C7	119.9 (2)	O4'—C7'—C6'	115.0 (2)
C5—C6—H6	120.0	O4'—C7'—C8'	123.6 (2)
C7—C6—H6	120.0	C6'—C7'—C8'	121.4 (2)
O4—C7—C8	123.6 (2)	C7'—C8'—C9'	116.8 (2)
O4—C7—C6	115.33 (19)	C7'—C8'—H8'	121.6
C8—C7—C6	121.0 (2)	C9'—C8'—H8'	121.6
C9—C8—C7	117.2 (2)	O1'—C9'—C4'	123.1 (2)
C9—C8—H8	121.4	O1'—C9'—C8'	112.8 (2)
C7—C8—H8	121.4	C4'—C9'—C8'	124.1 (2)
O1—C9—C8	112.95 (19)	O3'—C10'—C11'	107.92 (19)
O1—C9—C4	122.45 (19)	O3'—C10'—H10C	110.1
C8—C9—C4	124.6 (2)	C11'—C10'—H10C	110.1
O3—C10—C11	106.65 (18)	O3'—C10'—H10D	110.1
O3—C10—H10A	110.4	C11'—C10'—H10D	110.1
C11—C10—H10A	110.4	H10C—C10'—H10D	108.4
O3—C10—H10B	110.4	C12'—C11'—C16'	120.1 (2)
C11—C10—H10B	110.4	C12'—C11'—C10'	121.7 (2)
H10A—C10—H10B	108.6	C16'—C11'—C10'	118.3 (2)
C16—C11—C12	119.0 (2)	C11'—C12'—C13'	120.4 (2)
C16—C11—C10	118.8 (2)	C11'—C12'—H12'	119.8
C12—C11—C10	122.2 (2)	C13'—C12'—H12'	119.8
C13—C12—C11	120.1 (2)	C14'—C13'—C12'	118.8 (2)
C13—C12—H12	120.0	C14'—C13'—H13'	120.6
C11—C12—H12	120.0	C12'—C13'—H13'	120.6
C14—C13—C12	120.5 (2)	C15'—C14'—C13'	120.4 (2)
C14—C13—H13	119.7	C15'—C14'—H14'	119.8
C12—C13—H13	119.7	C13'—C14'—H14'	119.8
C13—C14—C15	119.2 (2)	C16'—C15'—C14'	121.5 (2)
C13—C14—H14	120.4	C16'—C15'—H15'	119.2
C15—C14—H14	120.4	C14'—C15'—H15'	119.2
C16—C15—C14	121.0 (2)	C15'—C16'—C11'	118.8 (3)
C16—C15—H15	119.5	C15'—C16'—H16'	120.6
C14—C15—H15	119.5	C11'—C16'—H16'	120.6
C15—C16—C11	120.2 (2)	O4'—C17'—C18'	107.88 (19)
C15—C16—H16	119.9	O4'—C17'—H17C	110.1
C11—C16—H16	119.9	C18'—C17'—H17C	110.1
O4—C17—C18	106.92 (17)	O4'—C17'—H17D	110.1
O4—C17—H17A	110.3	C18'—C17'—H17D	110.1
C18—C17—H17A	110.3	H17C—C17'—H17D	108.4
O4—C17—H17B	110.3	C19'—C18'—C23'	120.5 (2)
C18—C17—H17B	110.3	C19'—C18'—C17'	119.4 (2)
H17A—C17—H17B	108.6	C23'—C18'—C17'	119.9 (2)
C23—C18—C19	120.2 (2)	C18'—C19'—C20'	118.1 (2)
C23—C18—C17	118.1 (2)	C18'—C19'—H19'	121.0
C19—C18—C17	121.6 (2)	C20'—C19'—H19'	121.0
C20—C19—C18	119.6 (2)	C21'—C20'—C19'	121.4 (3)
C20—C19—H19	120.2	C21'—C20'—H20'	119.3
C18—C19—H19	120.2	C19'—C20'—H20'	119.3
C19—C20—C21	120.1 (2)	C22'—C21'—C20'	120.1 (2)
C19—C20—H20	119.9	C22'—C21'—H21'	120.0
C21—C20—H20	119.9	C20'—C21'—H21'	120.0
C22—C21—C20	120.0 (2)	C21'—C22'—C23'	120.8 (2)
C22—C21—H21	120.0	C21'—C22'—H22'	119.6
C20—C21—H21	120.0	C23'—C22'—H22'	119.6
C21—C22—C23	120.0 (2)	C18'—C23'—C22'	119.0 (2)
C21—C22—H22	120.0	C18'—C23'—H23'	120.5
C23—C22—H22	120.0	C22'—C23'—H23'	120.5
C18—C23—C22	120.0 (2)	C1—O1—C9	118.3 (2)
C18—C23—H23	120.0	C5—O3—C10	119.9 (2)
C22—C23—H23	120.0	C7—O4—C17	115.7 (2)
C2'—C1'—O1'	124.1 (2)	C1'—O1'—C9'	118.4 (2)
C2'—C1'—H1'	117.9	C5'—O3'—C10'	119.9 (2)
O1'—C1'—H1'	117.9	C7'—O4'—C17'	117.4 (2)
O1—C1—C2—C3	−1.8 (4)	C9'—C4'—C5'—C6'	0.4 (3)
C1—C2—C3—O2	−174.9 (2)	C3'—C4'—C5'—C6'	−179.4 (2)
C1—C2—C3—C4	2.5 (3)	O3'—C5'—C6'—C7'	179.9 (2)
O2—C3—C4—C9	174.9 (2)	C4'—C5'—C6'—C7'	−0.6 (4)
C2—C3—C4—C9	−2.4 (3)	C5'—C6'—C7'—O4'	−179.2 (2)
O2—C3—C4—C5	−4.7 (4)	C5'—C6'—C7'—C8'	0.6 (4)
C2—C3—C4—C5	178.1 (2)	O4'—C7'—C8'—C9'	179.3 (2)
C9—C4—C5—O3	179.70 (19)	C6'—C7'—C8'—C9'	−0.5 (4)
C3—C4—C5—O3	−0.7 (3)	C5'—C4'—C9'—O1'	179.0 (2)
C9—C4—C5—C6	−0.4 (3)	C3'—C4'—C9'—O1'	−1.2 (3)
C3—C4—C5—C6	179.2 (2)	C5'—C4'—C9'—C8'	−0.3 (4)
O3—C5—C6—C7	−179.3 (2)	C3'—C4'—C9'—C8'	179.5 (2)
C4—C5—C6—C7	0.8 (3)	C7'—C8'—C9'—O1'	−179.0 (2)
C5—C6—C7—O4	178.8 (2)	C7'—C8'—C9'—C4'	0.3 (4)
C5—C6—C7—C8	−2.2 (3)	O3'—C10'—C11'—C12'	0.9 (3)
O4—C7—C8—C9	−178.0 (2)	O3'—C10'—C11'—C16'	−178.0 (2)
C6—C7—C8—C9	3.1 (3)	C16'—C11'—C12'—C13'	−1.1 (3)
C7—C8—C9—O1	177.27 (19)	C10'—C11'—C12'—C13'	−179.9 (2)
C7—C8—C9—C4	−2.8 (3)	C11'—C12'—C13'—C14'	2.1 (3)
C5—C4—C9—O1	−178.7 (2)	C12'—C13'—C14'—C15'	−1.1 (3)
C3—C4—C9—O1	1.7 (3)	C13'—C14'—C15'—C16'	−0.9 (3)
C5—C4—C9—C8	1.4 (3)	C14'—C15'—C16'—C11'	2.0 (3)
C3—C4—C9—C8	−178.2 (2)	C12'—C11'—C16'—C15'	−1.0 (3)
O3—C10—C11—C16	178.4 (2)	C10'—C11'—C16'—C15'	177.9 (2)
O3—C10—C11—C12	−2.5 (3)	O4'—C17'—C18'—C19'	123.7 (2)
C16—C11—C12—C13	−1.0 (4)	O4'—C17'—C18'—C23'	−61.3 (3)
C10—C11—C12—C13	179.9 (2)	C23'—C18'—C19'—C20'	1.9 (4)
C11—C12—C13—C14	0.2 (4)	C17'—C18'—C19'—C20'	176.9 (2)
C12—C13—C14—C15	−0.1 (4)	C18'—C19'—C20'—C21'	0.5 (4)
C13—C14—C15—C16	0.9 (4)	C19'—C20'—C21'—C22'	−1.7 (4)
C14—C15—C16—C11	−1.7 (4)	C20'—C21'—C22'—C23'	0.4 (4)
C12—C11—C16—C15	1.7 (4)	C19'—C18'—C23'—C22'	−3.2 (4)
C10—C11—C16—C15	−179.2 (2)	C17'—C18'—C23'—C22'	−178.2 (2)
O4—C17—C18—C23	−107.2 (2)	C21'—C22'—C23'—C18'	2.0 (4)
O4—C17—C18—C19	76.2 (3)	C2—C1—O1—C9	0.9 (3)
C23—C18—C19—C20	−0.5 (4)	C8—C9—O1—C1	179.0 (2)
C17—C18—C19—C20	175.9 (2)	C4—C9—O1—C1	−0.9 (3)
C18—C19—C20—C21	1.1 (4)	C6—C5—O3—C10	2.7 (3)
C19—C20—C21—C22	−1.6 (4)	C4—C5—O3—C10	−177.34 (19)
C20—C21—C22—C23	1.4 (4)	C11—C10—O3—C5	173.06 (18)
C19—C18—C23—C22	0.3 (4)	C8—C7—O4—C17	4.3 (3)
C17—C18—C23—C22	−176.2 (2)	C6—C7—O4—C17	−176.71 (19)
C21—C22—C23—C18	−0.8 (4)	C18—C17—O4—C7	172.48 (19)
O1'—C1'—C2'—C3'	4.3 (4)	C2'—C1'—O1'—C9'	−2.3 (4)
C1'—C2'—C3'—O2'	173.6 (2)	C4'—C9'—O1'—C1'	0.8 (3)
C1'—C2'—C3'—C4'	−4.3 (3)	C8'—C9'—O1'—C1'	−179.9 (2)
O2'—C3'—C4'—C9'	−175.0 (2)	C6'—C5'—O3'—C10'	−8.4 (3)
C2'—C3'—C4'—C9'	2.8 (3)	C4'—C5'—O3'—C10'	172.0 (2)
O2'—C3'—C4'—C5'	4.8 (4)	C11'—C10'—O3'—C5'	−167.94 (19)
C2'—C3'—C4'—C5'	−177.4 (2)	C6'—C7'—O4'—C17'	174.5 (2)
C9'—C4'—C5'—O3'	180.0 (2)	C8'—C7'—O4'—C17'	−5.3 (3)
C3'—C4'—C5'—O3'	0.2 (3)	C18'—C17'—O4'—C7'	−178.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2	0.93	2.55	3.462 (3)	167
C12—H12···O3	0.93	2.30	2.648 (3)	102
C12′—H12′···O2′	0.93	2.58	3.494 (3)	169
C12′—H12′···O3′	0.93	2.30	2.665 (3)	103
C1—H1···O3′^i	0.93	2.58	3.508 (3)	173
C1′—H1′···O3^ii	0.93	2.53	3.439 (3)	165

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