(2RS)-3-(4-Hydroxy­phen­yl)-2-(1-oxo-1H-2,3-dihydro­isoindol-2-yl)propanoic acid monohydrate

The title compound, C₁₇H₁₅NO₄·H₂O, derived from DL-tyrosine crystallizes as an unusual hydrogen-bonded acid–monohydrate dimer. The asymmetric unit contains two organic molecules and two water molecules. Dimers link through (ar­yl)O—H...O=C hydrogen bonds along the [101] direction, forming a one-dimensional chain of rings, and further associated via inversion centres (forming a chain of rings aligned in the opposite direction) generating columns. Ruffled sheets arise from inter­locking of isoindole rings via π–π(arene) stacking and C—H...π(arene) inter­actions; C—H...O inter­actions generate a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.127
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O2W    -   H4     ...          ?

Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD4 (Enraf–Nonius, 1992); cell refinement: SET4 and CELDIM (Enraf–Nonius, 1992); data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).

(2RS)-3-(4-Hydroxyphenyl)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)propanoic acid monohydrate

Crystal data

C17H15NO4·H2O	? #Insert any comments here.
Mr = 315.32	Dx = 1.344 Mg m^−3
Monoclinic, P21/a	Melting point: 471 K
Hall symbol: -p 2yab	Mo Kα radiation, λ = 0.71073 Å
a = 15.5198 (10) Å	Cell parameters from 25 reflections
b = 14.7573 (12) Å	θ = 6.9–19.0°
c = 15.6383 (14) Å	µ = 0.10 mm^−1
β = 119.537 (7)°	T = 294 K
V = 3116.2 (5) Å^3	Block, colourless
Z = 8	0.35 × 0.35 × 0.27 mm
F(000) = 1328

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.019
Radiation source: X-ray tube	θmax = 25.5°, θmin = 2.0°
Graphite monochromator	h = −18→16
ω scans	k = 0→17
5983 measured reflections	l = 0→18
5769 independent reflections	3 standard reflections every 120 min
2889 reflections with I > 2σ(I)	intensity decay: 1%

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) = 0.127	w = 1/[σ^2(Fo^2) + (0.06P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
5769 reflections	Δρmax = 0.34 e Å^−3
432 parameters	Δρmin = −0.22 e Å^−3
6 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (6)

Special details

Experimental. ? #Insert any special details here.

Geometry. Mean plane data ex-SHELXL97 for molecule (I) ############################################

As detailed in the comment text section.

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

	x	y	z	Uiso*/Ueq
O1A	0.62002 (14)	0.02874 (16)	0.29413 (13)	0.0603 (6)
O2A	0.71245 (16)	−0.03636 (17)	0.24088 (14)	0.0766 (7)
O3A	0.79479 (14)	0.12793 (14)	0.53086 (14)	0.0579 (6)
O4A	1.09267 (16)	−0.18981 (13)	0.83315 (13)	0.0609 (6)
N1A	0.73612 (15)	−0.01553 (15)	0.47895 (14)	0.0402 (5)
C1A	0.70025 (19)	−0.0130 (2)	0.3068 (2)	0.0453 (7)
C2A	0.77755 (18)	−0.02502 (18)	0.41435 (17)	0.0396 (7)
C3A	0.7471 (2)	0.0603 (2)	0.53114 (18)	0.0442 (7)
C4A	0.6918 (2)	0.0469 (2)	0.58367 (19)	0.0477 (7)
C5A	0.6809 (2)	0.1034 (2)	0.6485 (2)	0.0673 (10)
C6A	0.6250 (3)	0.0731 (3)	0.6879 (3)	0.0858 (13)
C7A	0.5806 (3)	−0.0107 (3)	0.6640 (3)	0.0844 (13)
C8A	0.5906 (2)	−0.0677 (3)	0.5989 (2)	0.0715 (10)
C9A	0.6480 (2)	−0.0377 (2)	0.55973 (19)	0.0495 (8)
C10A	0.6726 (2)	−0.08331 (19)	0.4888 (2)	0.0494 (7)
C21A	0.83531 (18)	−0.11347 (18)	0.43053 (18)	0.0438 (7)
C11A	0.90736 (18)	−0.13253 (18)	0.53744 (18)	0.0385 (6)
C12A	0.9033 (2)	−0.21365 (19)	0.5790 (2)	0.0537 (8)
C13A	0.9657 (2)	−0.23224 (19)	0.6773 (2)	0.0562 (8)
C14A	1.03451 (19)	−0.16953 (19)	0.73616 (19)	0.0420 (7)
C15A	1.04195 (19)	−0.08858 (18)	0.69591 (19)	0.0422 (7)
C16A	0.97799 (19)	−0.07100 (18)	0.59740 (19)	0.0426 (7)
O1B	0.47713 (14)	0.15711 (19)	0.02018 (16)	0.0795 (8)
O2B	0.45929 (13)	0.06721 (15)	0.12382 (14)	0.0629 (6)
O3B	0.20959 (13)	−0.05032 (13)	−0.06916 (13)	0.0480 (5)
O4B	−0.13001 (14)	0.25457 (14)	−0.32320 (15)	0.0591 (6)
N1B	0.25838 (15)	0.08066 (14)	0.02076 (14)	0.0375 (5)
C1B	0.42485 (19)	0.1109 (2)	0.0496 (2)	0.0458 (7)
C2B	0.31435 (18)	0.11709 (18)	−0.02282 (18)	0.0398 (7)
C3B	0.20989 (17)	0.00129 (19)	−0.00563 (17)	0.0369 (6)
C4B	0.16106 (18)	−0.01116 (18)	0.05314 (18)	0.0391 (6)
C5B	0.0998 (2)	−0.08044 (19)	0.0514 (2)	0.0508 (8)
C6B	0.0637 (2)	−0.0753 (2)	0.1158 (2)	0.0608 (9)
C7B	0.0879 (2)	−0.0024 (3)	0.1797 (2)	0.0638 (9)
C8B	0.1467 (2)	0.0675 (2)	0.1795 (2)	0.0571 (8)
C9B	0.18369 (19)	0.06243 (19)	0.11546 (19)	0.0425 (7)
C10B	0.2480 (2)	0.12692 (19)	0.09809 (19)	0.0462 (7)
C21B	0.28150 (19)	0.21279 (18)	−0.06316 (19)	0.0454 (7)
C11B	0.17176 (19)	0.22209 (18)	−0.13099 (18)	0.0390 (6)
C12B	0.1234 (2)	0.16934 (19)	−0.21483 (19)	0.0484 (7)
C13B	0.0229 (2)	0.1794 (2)	−0.28023 (19)	0.0493 (7)
C14B	−0.03073 (19)	0.24285 (18)	−0.26180 (19)	0.0405 (7)
C15B	0.0152 (2)	0.29591 (18)	−0.17892 (19)	0.0452 (7)
C16B	0.1156 (2)	0.28504 (18)	−0.11483 (19)	0.0439 (7)
O1W	0.66876 (17)	0.15343 (19)	0.1355 (2)	0.0877 (8)
O2W	0.7860 (3)	0.2080 (3)	0.3412 (2)	0.1302 (12)
H1A	0.5831	0.0380	0.2354	0.090*
H4A	1.1279	−0.1462	0.8618	0.091*
H2A	0.8253	0.0244	0.4307	0.048*
H5A	0.7108	0.1602	0.6645	0.081*
H6A	0.6168	0.1097	0.7318	0.103*
H7A	0.5430	−0.0296	0.6921	0.101*
H8A	0.5598	−0.1241	0.5823	0.086*
H10A	0.7077	−0.1398	0.5153	0.059*
H10B	0.6135	−0.0950	0.4264	0.059*
H21A	0.7887	−0.1633	0.4037	0.053*
H21B	0.8715	−0.1105	0.3947	0.053*
H12A	0.8573	−0.2571	0.5398	0.064*
H13A	0.9611	−0.2874	0.7035	0.067*
H15A	1.0896	−0.0462	0.7347	0.051*
H16A	0.9829	−0.0160	0.5710	0.051*
H1B	0.5362	0.1501	0.0592	0.119*
H4B	−0.1510	0.2141	−0.3645	0.089*
H2B	0.3011	0.0782	−0.0788	0.048*
H5B	0.0836	−0.1288	0.0080	0.061*
H6B	0.0229	−0.1210	0.1166	0.073*
H7B	0.0638	−0.0006	0.2235	0.077*
H8B	0.1611	0.1167	0.2215	0.068*
H10C	0.2163	0.1855	0.0760	0.055*
H10D	0.3117	0.1349	0.1569	0.055*
H21C	0.3014	0.2542	−0.0084	0.054*
H21D	0.3157	0.2307	−0.0983	0.054*
H12B	0.1591	0.1261	−0.2276	0.058*
H13B	−0.0079	0.1433	−0.3362	0.059*
H15B	−0.0208	0.3388	−0.1660	0.054*
H16B	0.1461	0.3214	−0.0591	0.053*
H1	0.693 (3)	0.0971 (14)	0.136 (3)	0.132*
H2	0.701 (3)	0.171 (2)	0.2009 (11)	0.132*
H3	0.767 (3)	0.186 (4)	0.385 (3)	0.195*
H4	0.8514 (17)	0.226 (4)	0.387 (3)	0.195*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0432 (12)	0.0963 (17)	0.0388 (11)	0.0208 (12)	0.0182 (10)	0.0109 (12)
O2A	0.0731 (15)	0.124 (2)	0.0360 (11)	0.0412 (14)	0.0290 (11)	0.0116 (12)
O3A	0.0516 (12)	0.0550 (14)	0.0601 (14)	−0.0024 (11)	0.0222 (11)	−0.0117 (11)
O4A	0.0663 (15)	0.0541 (13)	0.0367 (11)	−0.0026 (11)	0.0056 (10)	0.0081 (10)
N1A	0.0369 (13)	0.0511 (14)	0.0321 (12)	0.0006 (11)	0.0166 (11)	−0.0025 (11)
C1A	0.0383 (16)	0.0605 (19)	0.0384 (16)	0.0046 (14)	0.0197 (14)	0.0042 (14)
C2A	0.0350 (14)	0.0532 (18)	0.0308 (14)	−0.0001 (13)	0.0163 (12)	−0.0028 (13)
C3A	0.0333 (15)	0.056 (2)	0.0323 (15)	0.0111 (15)	0.0076 (13)	0.0011 (15)
C4A	0.0422 (17)	0.061 (2)	0.0353 (16)	0.0178 (15)	0.0160 (14)	0.0022 (15)
C5A	0.062 (2)	0.091 (3)	0.0508 (19)	0.0238 (19)	0.0290 (18)	−0.0094 (18)
C6A	0.082 (3)	0.125 (4)	0.061 (2)	0.037 (3)	0.043 (2)	−0.003 (3)
C7A	0.069 (3)	0.143 (4)	0.061 (2)	0.037 (3)	0.048 (2)	0.029 (3)
C8A	0.064 (2)	0.098 (3)	0.066 (2)	0.015 (2)	0.0418 (19)	0.020 (2)
C9A	0.0462 (17)	0.069 (2)	0.0379 (16)	0.0169 (16)	0.0242 (15)	0.0104 (15)
C10A	0.0495 (17)	0.0543 (19)	0.0494 (17)	−0.0012 (15)	0.0281 (15)	−0.0016 (15)
C21A	0.0365 (15)	0.0564 (19)	0.0331 (15)	0.0016 (14)	0.0130 (13)	−0.0066 (14)
C11A	0.0348 (14)	0.0430 (17)	0.0349 (15)	−0.0006 (13)	0.0150 (13)	−0.0043 (13)
C12A	0.0478 (18)	0.0446 (19)	0.0517 (19)	−0.0115 (15)	0.0116 (16)	−0.0115 (15)
C13A	0.062 (2)	0.0391 (18)	0.0530 (19)	−0.0080 (15)	0.0168 (17)	0.0036 (15)
C14A	0.0426 (16)	0.0423 (17)	0.0331 (15)	0.0037 (14)	0.0127 (13)	−0.0008 (13)
C15A	0.0406 (16)	0.0414 (16)	0.0367 (15)	−0.0076 (13)	0.0130 (13)	−0.0019 (13)
C16A	0.0435 (16)	0.0428 (16)	0.0395 (15)	−0.0041 (13)	0.0191 (14)	0.0024 (13)
O1B	0.0379 (12)	0.130 (2)	0.0671 (16)	−0.0001 (14)	0.0231 (12)	0.0416 (15)
O2B	0.0394 (12)	0.0896 (17)	0.0497 (13)	0.0046 (11)	0.0144 (10)	0.0270 (12)
O3B	0.0471 (12)	0.0534 (12)	0.0430 (11)	−0.0017 (10)	0.0218 (10)	−0.0095 (10)
O4B	0.0419 (12)	0.0585 (14)	0.0608 (14)	0.0116 (10)	0.0129 (11)	−0.0042 (11)
N1B	0.0365 (12)	0.0435 (14)	0.0316 (12)	−0.0037 (11)	0.0160 (10)	−0.0022 (11)
C1B	0.0370 (16)	0.0612 (19)	0.0378 (16)	−0.0020 (15)	0.0174 (14)	0.0028 (15)
C2B	0.0355 (14)	0.0530 (18)	0.0298 (14)	−0.0042 (13)	0.0152 (12)	−0.0003 (13)
C3B	0.0295 (14)	0.0437 (17)	0.0302 (14)	0.0057 (13)	0.0092 (12)	0.0059 (13)
C4B	0.0341 (15)	0.0426 (16)	0.0372 (15)	0.0057 (13)	0.0150 (13)	0.0079 (13)
C5B	0.0452 (17)	0.0445 (18)	0.0620 (19)	0.0066 (14)	0.0258 (16)	0.0140 (15)
C6B	0.0508 (19)	0.065 (2)	0.075 (2)	0.0061 (17)	0.0369 (19)	0.0263 (19)
C7B	0.060 (2)	0.082 (3)	0.065 (2)	0.0179 (19)	0.0436 (18)	0.021 (2)
C8B	0.060 (2)	0.070 (2)	0.0507 (18)	0.0078 (17)	0.0348 (17)	0.0043 (16)
C9B	0.0369 (15)	0.0510 (18)	0.0367 (15)	0.0085 (13)	0.0159 (13)	0.0107 (14)
C10B	0.0500 (17)	0.0520 (18)	0.0376 (15)	−0.0020 (15)	0.0223 (14)	−0.0053 (14)
C21B	0.0421 (16)	0.0518 (18)	0.0352 (15)	−0.0097 (14)	0.0136 (13)	0.0007 (14)
C11B	0.0441 (16)	0.0415 (16)	0.0310 (14)	−0.0035 (13)	0.0182 (13)	0.0014 (12)
C12B	0.0428 (17)	0.0571 (19)	0.0426 (17)	0.0107 (15)	0.0190 (15)	−0.0061 (15)
C13B	0.0471 (18)	0.0548 (19)	0.0339 (16)	0.0054 (15)	0.0108 (14)	−0.0094 (14)
C14B	0.0385 (16)	0.0415 (16)	0.0400 (15)	0.0035 (13)	0.0181 (14)	0.0048 (14)
C15B	0.0552 (19)	0.0393 (17)	0.0446 (17)	0.0085 (14)	0.0273 (16)	−0.0013 (14)
C16B	0.0567 (19)	0.0392 (17)	0.0335 (15)	−0.0067 (14)	0.0204 (15)	−0.0051 (13)
O1W	0.0484 (14)	0.105 (2)	0.103 (2)	0.0066 (14)	0.0327 (14)	0.0354 (16)
O2W	0.148 (3)	0.124 (3)	0.152 (3)	−0.011 (2)	0.099 (3)	−0.012 (2)

Geometric parameters (Å, º)

O1A—C1A	1.314 (3)	N1B—C3B	1.343 (3)
O2A—C1A	1.187 (3)	N1B—C2B	1.446 (3)
O3A—C3A	1.244 (3)	N1B—C10B	1.465 (3)
O4A—C14A	1.362 (3)	C1B—C2B	1.522 (3)
N1A—C3A	1.346 (3)	C2B—C21B	1.528 (3)
N1A—C2A	1.447 (3)	C3B—C4B	1.463 (3)
N1A—C10A	1.465 (3)	C4B—C9B	1.384 (4)
C1A—C2A	1.520 (3)	C4B—C5B	1.387 (4)
C2A—C21A	1.532 (3)	C5B—C6B	1.374 (4)
C3A—C4A	1.465 (4)	C6B—C7B	1.388 (4)
C4A—C9A	1.382 (4)	C7B—C8B	1.377 (4)
C4A—C5A	1.385 (4)	C8B—C9B	1.381 (4)
C5A—C6A	1.365 (5)	C9B—C10B	1.498 (4)
C6A—C7A	1.374 (5)	C21B—C11B	1.505 (3)
C7A—C8A	1.387 (5)	C11B—C16B	1.380 (3)
C8A—C9A	1.379 (4)	C11B—C12B	1.385 (3)
C9A—C10A	1.499 (4)	C12B—C13B	1.388 (4)
C21A—C11A	1.510 (3)	C13B—C14B	1.375 (4)
C11A—C16A	1.375 (3)	C14B—C15B	1.375 (4)
C11A—C12A	1.378 (4)	C15B—C16B	1.385 (4)
C12A—C13A	1.382 (4)	O1A—H1A	0.8200
C13A—C14A	1.369 (4)	O4A—H4A	0.8200
C14A—C15A	1.381 (4)	O1B—H1B	0.8200
C15A—C16A	1.385 (3)	O4B—H4B	0.8200
O1B—C1B	1.305 (3)	O1W—H1	0.91 (3)
O2B—C1B	1.199 (3)	O1W—H2	0.92 (2)
O3B—C3B	1.250 (3)	O2W—H3	0.93 (3)
O4B—C14B	1.366 (3)	O2W—H4	0.95 (4)
C3A—N1A—C2A	122.5 (2)	O2B—C1B—O1B	124.4 (3)
C3A—N1A—C10A	113.2 (2)	O2B—C1B—C2B	123.6 (2)
C2A—N1A—C10A	124.1 (2)	O1B—C1B—C2B	112.0 (2)
O2A—C1A—O1A	123.4 (3)	N1B—C2B—C1B	110.2 (2)
O2A—C1A—C2A	123.4 (2)	N1B—C2B—C21B	112.5 (2)
O1A—C1A—C2A	113.2 (2)	C1B—C2B—C21B	112.8 (2)
N1A—C2A—C1A	112.4 (2)	O3B—C3B—N1B	123.9 (2)
N1A—C2A—C21A	113.1 (2)	O3B—C3B—C4B	128.5 (3)
C1A—C2A—C21A	111.1 (2)	N1B—C3B—C4B	107.6 (2)
O3A—C3A—N1A	124.2 (3)	C9B—C4B—C5B	121.7 (3)
O3A—C3A—C4A	128.7 (3)	C9B—C4B—C3B	108.3 (2)
N1A—C3A—C4A	107.1 (3)	C5B—C4B—C3B	130.0 (3)
C9A—C4A—C5A	121.4 (3)	C6B—C5B—C4B	117.9 (3)
C9A—C4A—C3A	108.5 (2)	C5B—C6B—C7B	120.5 (3)
C5A—C4A—C3A	130.2 (3)	C8B—C7B—C6B	121.5 (3)
C6A—C5A—C4A	117.9 (4)	C7B—C8B—C9B	118.3 (3)
C5A—C6A—C7A	121.1 (3)	C8B—C9B—C4B	120.1 (3)
C6A—C7A—C8A	121.6 (3)	C8B—C9B—C10B	130.6 (3)
C9A—C8A—C7A	117.4 (4)	C4B—C9B—C10B	109.4 (2)
C8A—C9A—C4A	120.6 (3)	N1B—C10B—C9B	102.0 (2)
C8A—C9A—C10A	129.8 (3)	C11B—C21B—C2B	114.0 (2)
C4A—C9A—C10A	109.6 (2)	C16B—C11B—C12B	117.1 (2)
N1A—C10A—C9A	101.6 (2)	C16B—C11B—C21B	122.0 (2)
C11A—C21A—C2A	113.3 (2)	C12B—C11B—C21B	120.9 (2)
C16A—C11A—C12A	117.3 (2)	C11B—C12B—C13B	121.7 (3)
C16A—C11A—C21A	122.5 (2)	C14B—C13B—C12B	119.6 (3)
C12A—C11A—C21A	120.2 (2)	O4B—C14B—C13B	121.9 (2)
C11A—C12A—C13A	121.8 (3)	O4B—C14B—C15B	118.1 (2)
C14A—C13A—C12A	120.0 (3)	C13B—C14B—C15B	120.0 (3)
O4A—C14A—C13A	118.0 (3)	C14B—C15B—C16B	119.5 (2)
O4A—C14A—C15A	122.6 (2)	C11B—C16B—C15B	122.2 (2)
C13A—C14A—C15A	119.4 (2)	C1A—O1A—H1A	109.5
C14A—C15A—C16A	119.6 (2)	C14A—O4A—H4A	109.5
C11A—C16A—C15A	121.9 (3)	C1B—O1B—H1B	109.5
C3B—N1B—C2B	123.7 (2)	C14B—O4B—H4B	109.5
C3B—N1B—C10B	112.8 (2)	H1—O1W—H2	105 (3)
C2B—N1B—C10B	123.5 (2)	H3—O2W—H4	99 (4)
C3A—N1A—C2A—C1A	−102.2 (3)	C3B—N1B—C2B—C1B	−107.9 (3)
C10A—N1A—C2A—C1A	73.1 (3)	C10B—N1B—C2B—C1B	72.6 (3)
C3A—N1A—C2A—C21A	131.0 (2)	C3B—N1B—C2B—C21B	125.4 (2)
C10A—N1A—C2A—C21A	−53.8 (3)	C10B—N1B—C2B—C21B	−54.2 (3)
O2A—C1A—C2A—N1A	−163.6 (3)	O2B—C1B—C2B—N1B	12.6 (4)
O1A—C1A—C2A—N1A	18.8 (3)	O1B—C1B—C2B—N1B	−168.7 (2)
O2A—C1A—C2A—C21A	−35.7 (4)	O2B—C1B—C2B—C21B	139.2 (3)
O1A—C1A—C2A—C21A	146.7 (2)	O1B—C1B—C2B—C21B	−42.1 (3)
C2A—N1A—C3A—O3A	−1.6 (4)	C2B—N1B—C3B—O3B	1.5 (4)
C10A—N1A—C3A—O3A	−177.3 (2)	C10B—N1B—C3B—O3B	−178.9 (2)
C2A—N1A—C3A—C4A	177.3 (2)	C2B—N1B—C3B—C4B	−178.9 (2)
C10A—N1A—C3A—C4A	1.6 (3)	C10B—N1B—C3B—C4B	0.7 (3)
O3A—C3A—C4A—C9A	178.2 (3)	O3B—C3B—C4B—C9B	178.7 (2)
N1A—C3A—C4A—C9A	−0.7 (3)	N1B—C3B—C4B—C9B	−0.9 (3)
O3A—C3A—C4A—C5A	−2.5 (5)	O3B—C3B—C4B—C5B	−2.7 (4)
N1A—C3A—C4A—C5A	178.6 (3)	N1B—C3B—C4B—C5B	177.8 (2)
C9A—C4A—C5A—C6A	−0.2 (4)	C9B—C4B—C5B—C6B	−1.7 (4)
C3A—C4A—C5A—C6A	−179.4 (3)	C3B—C4B—C5B—C6B	179.8 (3)
C4A—C5A—C6A—C7A	−0.2 (5)	C4B—C5B—C6B—C7B	0.5 (4)
C5A—C6A—C7A—C8A	−0.1 (6)	C5B—C6B—C7B—C8B	1.2 (5)
C6A—C7A—C8A—C9A	0.8 (5)	C6B—C7B—C8B—C9B	−1.6 (5)
C7A—C8A—C9A—C4A	−1.2 (4)	C7B—C8B—C9B—C4B	0.3 (4)
C7A—C8A—C9A—C10A	179.8 (3)	C7B—C8B—C9B—C10B	179.5 (3)
C5A—C4A—C9A—C8A	1.0 (4)	C5B—C4B—C9B—C8B	1.3 (4)
C3A—C4A—C9A—C8A	−179.7 (2)	C3B—C4B—C9B—C8B	−179.9 (2)
C5A—C4A—C9A—C10A	−179.8 (3)	C5B—C4B—C9B—C10B	−178.0 (2)
C3A—C4A—C9A—C10A	−0.5 (3)	C3B—C4B—C9B—C10B	0.7 (3)
C3A—N1A—C10A—C9A	−1.8 (3)	C3B—N1B—C10B—C9B	−0.2 (3)
C2A—N1A—C10A—C9A	−177.4 (2)	C2B—N1B—C10B—C9B	179.3 (2)
C8A—C9A—C10A—N1A	−179.6 (3)	C8B—C9B—C10B—N1B	−179.6 (3)
C4A—C9A—C10A—N1A	1.3 (3)	C4B—C9B—C10B—N1B	−0.3 (3)
N1A—C2A—C21A—C11A	−47.7 (3)	N1B—C2B—C21B—C11B	−51.7 (3)
C1A—C2A—C21A—C11A	−175.3 (2)	C1B—C2B—C21B—C11B	−177.1 (2)
C2A—C21A—C11A—C16A	−53.8 (3)	C2B—C21B—C11B—C16B	124.9 (3)
C2A—C21A—C11A—C12A	125.4 (3)	C2B—C21B—C11B—C12B	−57.4 (3)
C16A—C11A—C12A—C13A	1.5 (4)	C16B—C11B—C12B—C13B	0.3 (4)
C21A—C11A—C12A—C13A	−177.8 (3)	C21B—C11B—C12B—C13B	−177.5 (3)
C11A—C12A—C13A—C14A	−0.5 (5)	C11B—C12B—C13B—C14B	−0.3 (4)
C12A—C13A—C14A—O4A	178.3 (3)	C12B—C13B—C14B—O4B	−179.1 (3)
C12A—C13A—C14A—C15A	−1.2 (4)	C12B—C13B—C14B—C15B	0.0 (4)
O4A—C14A—C15A—C16A	−177.6 (3)	O4B—C14B—C15B—C16B	179.4 (2)
C13A—C14A—C15A—C16A	1.8 (4)	C13B—C14B—C15B—C16B	0.3 (4)
C12A—C11A—C16A—C15A	−0.8 (4)	C12B—C11B—C16B—C15B	−0.1 (4)
C21A—C11A—C16A—C15A	178.4 (2)	C21B—C11B—C16B—C15B	177.7 (2)
C14A—C15A—C16A—C11A	−0.8 (4)	C14B—C15B—C16B—C11B	−0.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2B	0.82	1.90	2.662 (3)	154
O1B—H1B···O1W	0.82	1.80	2.610 (3)	170
O1W—H1···O3B^i	0.91 (3)	2.33 (3)	2.982 (3)	128 (3)
O1W—H1···O2A	0.91 (3)	2.48 (3)	3.149 (3)	130 (3)
O1W—H2···O2W	0.92 (2)	2.00 (2)	2.921 (4)	172 (4)
O2W—H3···O3A	0.93 (3)	2.27 (5)	3.133 (4)	154 (4)
O4A—H4A···O3B^ii	0.82	1.85	2.670 (3)	178
O4B—H4B···O3A^iii	0.82	1.91	2.727 (3)	175
C2B—H2B···O2A^i	0.98	2.52	3.438 (3)	157
C12B—H12B···O2A^i	0.93	2.49	3.396 (3)	166
C21A—H21A···O4B^iv	0.97	2.46	3.390 (3)	160
C21B—H21C···O4A^v	0.97	2.54	3.448 (3)	156
C6A—H6A···Cg2^vi	0.93	2.83	3.707 (5)	158
C6B—H6B···Cg2^vii	0.93	2.85	3.723 (5)	157

Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z+1; (iii) x−1, y, z−1; (iv) −x+1/2, y−1/2, −z; (v) −x+3/2, y+1/2, −z+1; (vi) x−1/2, −y−1/2, z+1; (vii) −x, −y, −z.