Bis{(R)-N-[(R)-2-benz-yloxy-1-(4-tert-butyl-phen-yl)eth-yl]-2-methyl-propane-2-sulfinamide} monohydrate.

The asymmetric unit of the title compound, 2C23H33NO2S·H2O, contains one organic mol-ecule in a general position and one co-crystallized water mol-ecule on a crystallographic twofold axis. Each water mol-ecule serves as a hydrogen-bond donor to a pair of S=O acceptors on symmetry-related mol-ecules. Thus, each trio of mol-ecules forms one title formula unit. These groupings are further connected along [010] via weak non-classical C-H⋯O hydrogen bonds.

Related literature

For a general method to synthesize the Grignard reagent used in the reaction that generated the title material, see: Tilstam & Weinmann (2002 ▶). For in-depth discussions on methods to synthesize the precursor to the title mol­ecule from 2-butene-1,4-diol, see: Evans et al. (2008 ▶); Tang et al. (2001 ▶). For the importance of 1,2-amino­alcohols, see: Bergmeier (2000 ▶). For methods used to determine the absolute configuration, see: Flack (1983 ▶); Parsons & Flack (2004 ▶); Parsons et al. (2013 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

2C23H33NO2S·H2O

M = 793.14

Monoclinic,

a = 21.5717 (17) Å

b = 6.1097 (5) Å

c = 17.0838 (14) Å

β = 93.2220 (17)°

V = 2248.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 100 K

0.40 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEXII CCD platform diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2012 ▶) T min = 0.662, T max = 0.748

34281 measured reflections

12280 independent reflections

9359 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.110

S = 1.01

12280 reflections

385 parameters

1 restraint

All H-atom parameters refined

Δρmax = 0.46 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack parameter determined using 3436 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons & Flack, 2004 ▶)

Absolute structure parameter: −0.01 (3)

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2011 (Burla et al., 2012 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814004589/gk2604sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004589/gk2604Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004589/gk2604Isup3.cml

CCDC reference: 989104

Additional supporting information: crystallographic information; 3D view; checkCIF report

2C23H33NO2S·H2O	F(000) = 860
Mr = 793.14	Dx = 1.172 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 21.5717 (17) Å	Cell parameters from 4053 reflections
b = 6.1097 (5) Å	θ = 2.2–37.9°
c = 17.0838 (14) Å	µ = 0.16 mm−1
β = 93.2220 (17)°	T = 100 K
V = 2248.0 (3) Å3	Needle, colorless
Z = 2	0.40 × 0.18 × 0.16 mm

Bruker SMART APEXII CCD platform diffractometer	9359 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
ω scans	θmax = 38.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2012)	h = −37→37
Tmin = 0.662, Tmax = 0.748	k = −10→10
34281 measured reflections	l = −29→29
12280 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	All H-atom parameters refined
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0513P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
12280 reflections	Δρmax = 0.46 e Å−3
385 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack parameter determined using 3436 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (3)

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. All hydrogen atoms were found from the difference Fourier map and refined freely.The absolute configuration was deterimined using 3436 quotients, which gave a Flack parameter of -0.01 (3) (Parsons and Flack, 2004, Parson et al., 2013). This is essentially the same value obtained without Dobs(h) as a restraint, which resulted in a Flack parameter of -0.01 (4), calculated from 5617 Friedel pairs (Flack, 1983).

	x	y	z	Uiso*/Ueq
S1	0.42226 (2)	0.46312 (7)	0.15482 (2)	0.01727 (8)
O1	0.58554 (6)	0.8370 (2)	0.16151 (7)	0.0209 (2)
O2	0.46240 (7)	0.2778 (2)	0.13077 (8)	0.0285 (3)
N1	0.46287 (6)	0.6943 (2)	0.16175 (8)	0.0163 (2)
H1N	0.4839 (11)	0.719 (4)	0.1199 (14)	0.030 (6)*
C1	0.50207 (7)	0.7109 (3)	0.23545 (9)	0.0161 (3)
H1	0.5262 (10)	0.574 (4)	0.2460 (12)	0.016 (5)*
C2	0.54948 (7)	0.8923 (3)	0.22575 (9)	0.0178 (3)
H2A	0.5281 (10)	1.029 (4)	0.2189 (14)	0.023 (6)*
H2B	0.5749 (9)	0.904 (3)	0.2734 (12)	0.012 (5)*
C3	0.62305 (8)	1.0173 (3)	0.13942 (10)	0.0227 (3)
H3A	0.5959 (11)	1.147 (4)	0.1336 (13)	0.022 (6)*
H3B	0.6351 (9)	0.979 (4)	0.0868 (13)	0.022 (5)*
C4	0.67655 (8)	1.0589 (3)	0.19842 (9)	0.0197 (3)
C5	0.68504 (9)	1.2612 (3)	0.23440 (11)	0.0255 (4)
H5	0.6574 (12)	1.379 (5)	0.2226 (15)	0.037 (7)*
C6	0.73526 (11)	1.2977 (4)	0.28735 (12)	0.0341 (5)
H6	0.7411 (11)	1.431 (5)	0.3100 (15)	0.036 (7)*
C7	0.77729 (10)	1.1315 (4)	0.30506 (13)	0.0349 (5)
H7	0.8120 (12)	1.157 (5)	0.3420 (15)	0.041 (7)*
C8	0.76889 (9)	0.9273 (4)	0.27026 (12)	0.0314 (5)
H8	0.7981 (13)	0.816 (5)	0.2848 (16)	0.046 (8)*
C9	0.71873 (8)	0.8916 (3)	0.21733 (11)	0.0242 (3)
H9	0.7099 (12)	0.759 (5)	0.1917 (14)	0.033 (7)*
C10	0.46395 (7)	0.7656 (3)	0.30471 (8)	0.0154 (3)
C11	0.46392 (7)	0.6297 (3)	0.36989 (10)	0.0177 (3)
H11	0.4859 (10)	0.499 (4)	0.3673 (13)	0.024 (6)*
C12	0.43313 (8)	0.6904 (3)	0.43609 (9)	0.0181 (3)
H12	0.4333 (10)	0.594 (4)	0.4788 (13)	0.025 (6)*
C13	0.40197 (7)	0.8894 (3)	0.44018 (9)	0.0161 (3)
C14	0.40172 (7)	1.0238 (3)	0.37349 (10)	0.0184 (3)
H14	0.3801 (11)	1.162 (4)	0.3734 (13)	0.024 (6)*
C15	0.43132 (7)	0.9623 (3)	0.30689 (9)	0.0185 (3)
H15	0.4295 (10)	1.052 (4)	0.2600 (13)	0.024 (6)*
C16	0.37205 (7)	0.9653 (4)	0.51461 (9)	0.0192 (3)
C17	0.35710 (9)	0.7726 (4)	0.56789 (11)	0.0248 (4)
H17A	0.3367 (10)	0.810 (4)	0.6113 (13)	0.025 (6)*
H17B	0.3945 (12)	0.696 (5)	0.5893 (14)	0.034 (7)*
H17C	0.3302 (12)	0.670 (5)	0.5370 (15)	0.039 (7)*
C18	0.31087 (10)	1.0872 (5)	0.49419 (13)	0.0340 (5)
H18A	0.2904 (12)	1.139 (5)	0.5422 (15)	0.038 (7)*
H18B	0.2843 (13)	1.004 (5)	0.4603 (18)	0.051 (8)*
H18C	0.3177 (11)	1.213 (5)	0.4672 (15)	0.032 (7)*
C19	0.41775 (9)	1.1181 (3)	0.55980 (11)	0.0249 (3)
H19A	0.4012 (10)	1.170 (4)	0.6085 (13)	0.020 (5)*
H19B	0.4268 (10)	1.243 (4)	0.5268 (12)	0.018 (5)*
H19C	0.4586 (9)	1.037 (4)	0.5743 (12)	0.017 (5)*
C20	0.37165 (7)	0.5317 (3)	0.06805 (10)	0.0182 (3)
C21	0.40958 (8)	0.5784 (3)	−0.00242 (10)	0.0215 (3)
H21A	0.3833 (11)	0.591 (4)	−0.0478 (14)	0.026 (6)*
H21B	0.4409 (10)	0.450 (5)	−0.0104 (14)	0.030 (6)*
H21C	0.4312 (11)	0.717 (4)	0.0028 (13)	0.023 (6)*
C22	0.33246 (10)	0.3261 (4)	0.05314 (12)	0.0293 (4)
H22A	0.3027 (14)	0.348 (6)	0.0101 (18)	0.052 (8)*
H22B	0.3099 (12)	0.280 (5)	0.0976 (15)	0.030 (6)*
H22C	0.3551 (13)	0.198 (5)	0.0423 (16)	0.049 (8)*
C23	0.33169 (9)	0.7248 (4)	0.09006 (12)	0.0269 (4)
H23A	0.2998 (13)	0.757 (5)	0.0466 (16)	0.047 (8)*
H23B	0.3557 (11)	0.851 (4)	0.0981 (14)	0.029 (6)*
H23C	0.3068 (11)	0.692 (4)	0.1352 (14)	0.028 (6)*
O3	0.5000	0.0337 (4)	0.0000	0.0323 (4)
H3O	0.4903 (13)	0.116 (5)	0.0355 (16)	0.047 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.01922 (16)	0.01591 (15)	0.01623 (15)	−0.00308 (15)	−0.00284 (12)	0.00315 (15)
O1	0.0192 (5)	0.0285 (6)	0.0150 (5)	−0.0090 (5)	0.0021 (4)	−0.0026 (4)
O2	0.0358 (7)	0.0181 (6)	0.0304 (7)	0.0067 (5)	−0.0080 (6)	0.0006 (5)
N1	0.0162 (6)	0.0182 (6)	0.0140 (5)	−0.0052 (5)	−0.0017 (4)	0.0013 (5)
C1	0.0150 (6)	0.0194 (7)	0.0137 (6)	0.0000 (5)	−0.0018 (5)	0.0007 (5)
C2	0.0153 (6)	0.0233 (7)	0.0146 (6)	−0.0031 (6)	−0.0005 (5)	−0.0011 (6)
C3	0.0225 (7)	0.0301 (9)	0.0152 (7)	−0.0099 (6)	−0.0015 (6)	0.0035 (6)
C4	0.0181 (7)	0.0251 (8)	0.0157 (6)	−0.0066 (6)	0.0011 (5)	0.0007 (6)
C5	0.0281 (9)	0.0244 (9)	0.0241 (8)	−0.0056 (7)	0.0014 (7)	−0.0009 (7)
C6	0.0412 (11)	0.0354 (11)	0.0253 (9)	−0.0187 (9)	−0.0020 (8)	−0.0050 (8)
C7	0.0265 (9)	0.0502 (13)	0.0267 (9)	−0.0176 (9)	−0.0092 (7)	0.0087 (9)
C8	0.0203 (7)	0.0418 (13)	0.0316 (9)	−0.0043 (8)	−0.0033 (7)	0.0136 (9)
C9	0.0235 (8)	0.0252 (8)	0.0241 (8)	−0.0047 (7)	0.0024 (6)	0.0027 (7)
C10	0.0139 (6)	0.0184 (7)	0.0134 (6)	−0.0015 (5)	−0.0025 (5)	0.0013 (5)
C11	0.0189 (7)	0.0162 (7)	0.0178 (7)	0.0006 (6)	0.0005 (5)	0.0022 (5)
C12	0.0192 (7)	0.0194 (7)	0.0156 (6)	0.0007 (6)	0.0002 (5)	0.0033 (5)
C13	0.0132 (6)	0.0198 (7)	0.0149 (6)	−0.0014 (5)	−0.0023 (5)	0.0000 (5)
C14	0.0168 (6)	0.0184 (7)	0.0197 (7)	0.0030 (5)	−0.0004 (5)	0.0029 (5)
C15	0.0179 (6)	0.0210 (6)	0.0166 (6)	0.0020 (7)	0.0001 (5)	0.0050 (7)
C16	0.0175 (6)	0.0245 (7)	0.0156 (6)	0.0022 (7)	−0.0007 (5)	−0.0018 (7)
C17	0.0237 (8)	0.0308 (9)	0.0205 (8)	−0.0048 (7)	0.0062 (6)	−0.0014 (7)
C18	0.0269 (9)	0.0531 (15)	0.0220 (9)	0.0182 (9)	0.0004 (7)	−0.0013 (9)
C19	0.0328 (9)	0.0221 (8)	0.0195 (8)	−0.0039 (7)	−0.0018 (7)	−0.0022 (6)
C20	0.0157 (6)	0.0195 (7)	0.0189 (7)	−0.0039 (5)	−0.0030 (5)	0.0023 (5)
C21	0.0233 (7)	0.0233 (8)	0.0174 (7)	−0.0027 (6)	−0.0024 (6)	0.0046 (6)
C22	0.0283 (9)	0.0320 (10)	0.0270 (9)	−0.0142 (8)	−0.0033 (7)	−0.0004 (8)
C23	0.0206 (8)	0.0292 (10)	0.0307 (9)	0.0044 (7)	−0.0012 (7)	0.0029 (8)
O3	0.0374 (11)	0.0194 (9)	0.0399 (12)	0.000	0.0008 (10)	0.000

S1—O2	1.4967 (14)	C12—H12	0.94 (2)
S1—N1	1.6628 (14)	C13—C14	1.404 (2)
S1—C20	1.8394 (16)	C13—C16	1.530 (2)
O1—C2	1.421 (2)	C14—C15	1.387 (2)
O1—C3	1.430 (2)	C14—H14	0.96 (2)
N1—C1	1.480 (2)	C15—H15	0.97 (2)
N1—H1N	0.88 (2)	C16—C17	1.533 (3)
C1—C10	1.516 (2)	C16—C19	1.534 (3)
C1—C2	1.523 (2)	C16—C18	1.538 (3)
C1—H1	1.00 (2)	C17—H17A	0.91 (2)
C2—H2A	0.96 (2)	C17—H17B	0.99 (3)
C2—H2B	0.96 (2)	C17—H17C	0.99 (3)
C3—C4	1.511 (2)	C18—H18A	1.00 (3)
C3—H3A	0.99 (2)	C18—H18B	0.94 (3)
C3—H3B	0.98 (2)	C18—H18C	0.91 (3)
C4—C5	1.388 (3)	C19—H19A	0.98 (2)
C4—C9	1.394 (3)	C19—H19B	0.97 (2)
C5—C6	1.390 (3)	C19—H19C	1.03 (2)
C5—H5	0.95 (3)	C20—C21	1.520 (2)
C6—C7	1.383 (4)	C20—C23	1.521 (3)
C6—H6	0.91 (3)	C20—C22	1.527 (3)
C7—C8	1.390 (4)	C21—H21A	0.94 (2)
C7—H7	0.96 (3)	C21—H21B	1.05 (3)
C8—C9	1.388 (3)	C21—H21C	0.97 (2)
C8—H8	0.95 (3)	C22—H22A	0.96 (3)
C9—H9	0.94 (3)	C22—H22B	0.97 (3)
C10—C11	1.389 (2)	C22—H22C	0.94 (3)
C10—C15	1.394 (2)	C23—H23A	1.00 (3)
C11—C12	1.394 (2)	C23—H23B	0.94 (3)
C11—H11	0.93 (2)	C23—H23C	0.99 (2)
C12—C13	1.393 (2)	O3—H3O	0.82 (3)
O2—S1—N1	110.59 (8)	C15—C14—C13	121.74 (16)
O2—S1—C20	106.10 (8)	C15—C14—H14	118.7 (14)
N1—S1—C20	98.65 (7)	C13—C14—H14	119.5 (14)
C2—O1—C3	111.30 (14)	C14—C15—C10	120.77 (15)
C1—N1—S1	113.10 (11)	C14—C15—H15	121.8 (13)
C1—N1—H1N	112.5 (16)	C10—C15—H15	117.4 (13)
S1—N1—H1N	112.5 (17)	C13—C16—C17	111.92 (16)
N1—C1—C10	111.72 (12)	C13—C16—C19	108.26 (13)
N1—C1—C2	108.20 (13)	C17—C16—C19	108.61 (14)
C10—C1—C2	108.77 (13)	C13—C16—C18	110.78 (13)
N1—C1—H1	111.3 (12)	C17—C16—C18	107.46 (16)
C10—C1—H1	110.2 (12)	C19—C16—C18	109.78 (18)
C2—C1—H1	106.4 (12)	C16—C17—H17A	114.7 (15)
O1—C2—C1	108.14 (13)	C16—C17—H17B	113.0 (15)
O1—C2—H2A	113.2 (14)	H17A—C17—H17B	103.8 (19)
C1—C2—H2A	109.1 (13)	C16—C17—H17C	107.9 (16)
O1—C2—H2B	111.2 (11)	H17A—C17—H17C	107 (2)
C1—C2—H2B	108.4 (12)	H17B—C17—H17C	110 (2)
H2A—C2—H2B	106.8 (19)	C16—C18—H18A	112.2 (15)
O1—C3—C4	112.08 (14)	C16—C18—H18B	111.4 (19)
O1—C3—H3A	107.7 (13)	H18A—C18—H18B	113 (2)
C4—C3—H3A	111.0 (14)	C16—C18—H18C	111.1 (16)
O1—C3—H3B	103.9 (14)	H18A—C18—H18C	104 (2)
C4—C3—H3B	114.9 (12)	H18B—C18—H18C	105 (2)
H3A—C3—H3B	106.7 (18)	C16—C19—H19A	111.7 (13)
C5—C4—C9	118.82 (17)	C16—C19—H19B	109.2 (13)
C5—C4—C3	121.48 (17)	H19A—C19—H19B	109.6 (18)
C9—C4—C3	119.70 (17)	C16—C19—H19C	110.3 (12)
C4—C5—C6	120.6 (2)	H19A—C19—H19C	107.4 (18)
C4—C5—H5	121.0 (16)	H19B—C19—H19C	108.5 (17)
C6—C5—H5	118.3 (17)	C21—C20—C23	112.84 (15)
C7—C6—C5	120.1 (2)	C21—C20—C22	109.86 (15)
C7—C6—H6	119.5 (16)	C23—C20—C22	111.29 (15)
C5—C6—H6	120.3 (16)	C21—C20—S1	111.06 (11)
C6—C7—C8	119.82 (19)	C23—C20—S1	107.24 (12)
C6—C7—H7	120.2 (17)	C22—C20—S1	104.18 (12)
C8—C7—H7	120.0 (17)	C20—C21—H21A	110.1 (14)
C9—C8—C7	119.9 (2)	C20—C21—H21B	110.0 (13)
C9—C8—H8	122.6 (18)	H21A—C21—H21B	109 (2)
C7—C8—H8	117.6 (18)	C20—C21—H21C	111.6 (13)
C8—C9—C4	120.71 (19)	H21A—C21—H21C	106 (2)
C8—C9—H9	124.8 (16)	H21B—C21—H21C	110.8 (19)
C4—C9—H9	114.5 (16)	C20—C22—H22A	111 (2)
C11—C10—C15	118.08 (14)	C20—C22—H22B	114.0 (16)
C11—C10—C1	121.25 (15)	H22A—C22—H22B	107 (2)
C15—C10—C1	120.51 (13)	C20—C22—H22C	115.1 (18)
C10—C11—C12	120.89 (15)	H22A—C22—H22C	107 (3)
C10—C11—H11	116.9 (14)	H22B—C22—H22C	102 (2)
C12—C11—H11	122.2 (14)	C20—C23—H23A	110.2 (17)
C13—C12—C11	121.75 (15)	C20—C23—H23B	111.1 (15)
C13—C12—H12	119.3 (14)	H23A—C23—H23B	107 (2)
C11—C12—H12	118.9 (14)	C20—C23—H23C	112.1 (15)
C12—C13—C14	116.72 (14)	H23A—C23—H23C	104 (2)
C12—C13—C16	122.24 (15)	H23B—C23—H23C	112 (2)
C14—C13—C16	120.98 (15)
O2—S1—N1—C1	−79.01 (13)	C15—C10—C11—C12	−1.2 (2)
C20—S1—N1—C1	170.09 (11)	C1—C10—C11—C12	174.35 (15)
S1—N1—C1—C10	−75.83 (16)	C10—C11—C12—C13	−0.8 (3)
S1—N1—C1—C2	164.47 (11)	C11—C12—C13—C14	1.6 (2)
C3—O1—C2—C1	169.06 (13)	C11—C12—C13—C16	−175.44 (15)
N1—C1—C2—O1	−59.44 (17)	C12—C13—C14—C15	−0.4 (2)
C10—C1—C2—O1	179.02 (13)	C16—C13—C14—C15	176.72 (15)
C2—O1—C3—C4	72.42 (18)	C13—C14—C15—C10	−1.7 (3)
O1—C3—C4—C5	−123.42 (18)	C11—C10—C15—C14	2.4 (2)
O1—C3—C4—C9	56.8 (2)	C1—C10—C15—C14	−173.17 (15)
C9—C4—C5—C6	1.1 (3)	C12—C13—C16—C17	−23.2 (2)
C3—C4—C5—C6	−178.68 (17)	C14—C13—C16—C17	159.92 (15)
C4—C5—C6—C7	−0.3 (3)	C12—C13—C16—C19	96.5 (2)
C5—C6—C7—C8	−0.5 (3)	C14—C13—C16—C19	−80.41 (19)
C6—C7—C8—C9	0.6 (3)	C12—C13—C16—C18	−143.07 (19)
C7—C8—C9—C4	0.1 (3)	C14—C13—C16—C18	40.0 (2)
C5—C4—C9—C8	−1.0 (3)	O2—S1—C20—C21	−54.50 (14)
C3—C4—C9—C8	178.79 (16)	N1—S1—C20—C21	59.96 (13)
N1—C1—C10—C11	122.18 (16)	O2—S1—C20—C23	−178.21 (12)
C2—C1—C10—C11	−118.45 (17)	N1—S1—C20—C23	−63.75 (13)
N1—C1—C10—C15	−62.37 (19)	O2—S1—C20—C22	63.72 (14)
C2—C1—C10—C15	56.99 (18)	N1—S1—C20—C22	178.18 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2	0.82 (3)	2.02 (3)	2.8420 (19)	171 (3)
C2—H2A···O2i	0.96 (2)	2.52 (2)	3.372 (2)	148.1 (19)
C21—H21C···O3i	0.97 (2)	2.44 (2)	3.397 (3)	169.0 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2	0.82 (3)	2.02 (3)	2.8420 (19)	171 (3)
C2—H2A⋯O2i	0.96 (2)	2.52 (2)	3.372 (2)	148.1 (19)
C21—H21C⋯O3i	0.97 (2)	2.44 (2)	3.397 (3)	169.0 (19)

Symmetry code: (i) .