Triaqua­(5-formyl-N-salicyl­idene-DL-alaninato-κ³N,O,O′)nickel(II) monohydrate

The deprotonated Schiff-base dianion in the title compound, [Ni(C₁₁H₉NO₄)(H₂O)₃]·H₂O, occupies the meridional sites of the NiO₅N octa­hedron. The neutral complex mol­ecule inter­acts with the uncoordinated water mol­ecule by way of O—H...O hydrogen bonds to give rise to a three-dimensional network. The ethylidene part of the molecule is disordered over two positions in a 0.74:0.26 ratio.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.036
• wR factor = 0.099
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        300 Deg.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.04
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         11
PLAT731_ALERT_1_C Bond    Calc     0.84(3), Rep   0.845(10) ......       3.00 su-Ra
              O1W  -H1W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.845(10) ......       3.00 su-Ra
              O2W  -H2W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Ra
              O3W  -H3W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(3), Rep   0.847(10) ......       3.00 su-Ra
              O3W  -H3W2    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.850(10) ......       3.00 su-Ra
              O1W  -H4#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O2W  -H6#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Ra
              O3W  -H8#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.850(10) ......       3.00 su-Ra
              O3W  -H9#     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.95(3), Rep   1.950(10) ......       3.00 su-Ra
              H4#  -O1      1.555   2.666
PLAT736_ALERT_1_C H...A   Calc     1.93(3), Rep   1.930(10) ......       3.00 su-Ra
              H6#  -O3      1.555   2.676
PLAT736_ALERT_1_C H...A   Calc     1.94(3), Rep   1.950(10) ......       3.00 su-Ra
              H8#  -O2      1.555   2.766
PLAT736_ALERT_1_C H...A   Calc     1.85(3), Rep   1.850(10) ......       3.00 su-Ra
              H9#  -O4W     1.555   1.565
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      29.30 Deg.
              C2   -N1   -C2'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.40 Deg.
              C2   -C1   -C2'     1.555   1.555   1.555

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C2'    = ...          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         35

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

  15 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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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S1. Comment

The salicylidene-glycine carboxylic acid when doubly deprotonated generally chelates to metal centers through its N,O,O' atoms. The planar ligand chelates to nickel in this manner in, for example, the tripyridinenickel complex for which it occupies the meridional sites (Cui et al., 1992). The 3-methoxy analog also affords a six-coordinate tripyridine complex, but it also contains ethanol as the solvate molecule (Cui et al., 1993). The N-(5-bromosalicylidene)tryptophanate complex is a triaqua complex that crystallizes with two uncoordinated water molecules (Rodríguez et al., 1990).

This chelating feature is also found in the title compound, (I), (Table 1) which has a formyl group as substituent in the aromatic ring. The formyl substitutent in involved in hydrogen bonding interactions with the water molecules to give rise to a three-dimenional network architecture (Table 2).

Related literature

For the structures of other salicylidene-glycine-nickel complexes, see Cui et al. (1992, 1993); Rodríguez et al. (1990).

S2. Experimental

5-Formylsalicylaldehyde (0.2 mmol, 0.27 g), D,L-alanine (0.2 mmol, 0.18 g) and potassium hydroxide (0.2 mmol, 0.11 g) were dissolved in 80% aqueous methanol (15 ml). The mixture was stirred for 1 h to give a clear yellow solution. To the solution was added an aqueous solution (15 ml) of nickel(II) acetate hexahydrate (0.2 mmol, 0.57 g). The mixture heated at 323 K for 3 h. Green crystals of (I) were obtained in about 50% yield.

S3. Refinement

The ethylidene part of the molecule is disordered over two positions; the disorder refined to a 0.737 (11):0.263 (11) ratio. Pairs of equivalent carbon-carbon distances were restrained to within 0.01 Å of each other, and the disordered atoms were restrained to vibrate in a nearly isotropic manner.

The carbon-bound H atoms were placed in calculated positions (C—H 0.93 Å), and were included in the refinement in the riding model approximation, with U_iso(H) = 1.2U_eq(C).

The water H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O–H = 0.85±0.01 Å; U_iso was freely varied for each H atom.

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).

Figures

Fig. 1. View of (I) as a displacement ellipsoid plot (50% probability). Hydrogen atoms are drawn as spheres of arbitrary radii; the minor disorder component is not shown.

Triaqua(5-formyl-N-salicylidene-D,L-alaninato-κ³N,\ O,O')nickel(II) monohydrate

Crystal data

[Ni(C11H9NO4)(H2O)3].H2O	Z = 2
Mr = 349.97	F(000) = 364
Triclinic, P1	Dx = 1.647 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.861 (2) Å	Cell parameters from 2418 reflections
b = 8.664 (2) Å	θ = 2.3–27.1°
c = 12.363 (3) Å	µ = 1.41 mm^−1
α = 82.967 (3)°	T = 295 K
β = 80.639 (3)°	Block, green
γ = 77.706 (3)°	0.20 × 0.10 × 0.05 mm
V = 705.5 (3) Å^3

Data collection

Bruker SMART CCD diffractometer	2966 independent reflections
Radiation source: fine-focus sealed tube	2635 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 27.1°, θmin = 1.7°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −5→8
Tmin = 0.870, Tmax = 0.933	k = −9→11
4072 measured reflections	l = −14→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.059P)^2 + 0.1949P] where P = (Fo^2 + 2Fc^2)/3
2966 reflections	(Δ/σ)max = 0.001
241 parameters	Δρmax = 0.55 e Å^−3
35 restraints	Δρmin = −0.43 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.62546 (4)	0.75271 (3)	0.39426 (2)	0.02769 (12)
O1	0.7525 (3)	0.52716 (18)	0.44937 (13)	0.0347 (4)
O2	0.9267 (3)	0.3003 (2)	0.39286 (16)	0.0463 (5)
O3	0.5195 (3)	0.96942 (18)	0.32259 (13)	0.0315 (4)
O4	0.6313 (4)	1.3584 (2)	−0.14612 (15)	0.0495 (5)
O1W	0.3722 (3)	0.6685 (2)	0.36805 (15)	0.0396 (4)
O2W	0.4613 (3)	0.8013 (2)	0.54397 (15)	0.0382 (4)
O3W	0.8478 (3)	0.8416 (2)	0.44387 (17)	0.0445 (5)
O4W	1.0881 (3)	0.0138 (2)	0.31021 (19)	0.0474 (5)
N1	0.7874 (3)	0.6852 (2)	0.25235 (17)	0.0356 (5)
C1	0.8554 (4)	0.4445 (3)	0.3764 (2)	0.0355 (5)
C2	0.9180 (6)	0.5251 (4)	0.2619 (3)	0.0302 (10)	0.737 (11)
H2	1.0598	0.5342	0.2535	0.036*	0.737 (11)
C3	0.8859 (14)	0.4276 (7)	0.1736 (6)	0.065 (2)	0.737 (11)
H3A	0.9225	0.3167	0.1967	0.097*	0.737 (11)
H3B	0.9684	0.4520	0.1058	0.097*	0.737 (11)
H3C	0.7468	0.4529	0.1630	0.097*	0.737 (11)
C2'	0.817 (2)	0.5062 (9)	0.2564 (6)	0.045 (4)	0.263 (11)
H2'	0.6895	0.4803	0.2457	0.054*	0.263 (11)
C3'	0.980 (2)	0.430 (2)	0.1702 (14)	0.049 (4)	0.263 (11)
H3'1	0.9542	0.4786	0.0985	0.073*	0.263 (11)
H3'2	0.9805	0.3190	0.1744	0.073*	0.263 (11)
H3'3	1.1085	0.4456	0.1831	0.073*	0.263 (11)
C4	0.8019 (4)	0.7699 (3)	0.1609 (2)	0.0361 (5)
H4	0.8834	0.7222	0.1015	0.043*
C5	0.7030 (3)	0.9339 (3)	0.14088 (18)	0.0284 (5)
C6	0.7401 (4)	1.0054 (3)	0.03400 (19)	0.0320 (5)
H6	0.8249	0.9459	−0.0190	0.038*
C7	0.6553 (4)	1.1611 (3)	0.00411 (19)	0.0326 (5)
C8	0.5282 (4)	1.2502 (3)	0.0832 (2)	0.0372 (5)
H8	0.4712	1.3555	0.0643	0.045*
C9	0.4865 (4)	1.1843 (3)	0.1885 (2)	0.0375 (6)
H9	0.4005	1.2458	0.2400	0.045*
C10	0.5710 (3)	1.0242 (3)	0.22144 (18)	0.0279 (4)
C11	0.6961 (4)	1.2240 (3)	−0.1101 (2)	0.0386 (6)
H11	0.7779	1.1560	−0.1590	0.046*
H1W1	0.336 (5)	0.601 (3)	0.418 (2)	0.058 (10)*
H1W2	0.369 (6)	0.640 (4)	0.3058 (16)	0.066 (11)*
H2W1	0.473 (6)	0.875 (3)	0.580 (3)	0.065 (11)*
H2W2	0.3354 (18)	0.810 (4)	0.548 (3)	0.069 (12)*
H3W1	0.933 (4)	0.787 (3)	0.482 (2)	0.046 (9)*
H3W2	0.930 (4)	0.886 (4)	0.399 (2)	0.061 (11)*
H4W1	1.048 (5)	0.1082 (18)	0.326 (3)	0.052 (9)*
H4W2	1.207 (3)	−0.009 (4)	0.325 (3)	0.071 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.03501 (19)	0.02257 (17)	0.02212 (17)	−0.00216 (12)	−0.00137 (12)	0.00139 (11)
O1	0.0449 (10)	0.0265 (8)	0.0270 (8)	−0.0007 (7)	0.0002 (7)	0.0024 (6)
O2	0.0660 (13)	0.0256 (8)	0.0379 (10)	0.0062 (8)	−0.0041 (9)	0.0025 (7)
O3	0.0409 (9)	0.0247 (7)	0.0234 (8)	−0.0008 (7)	0.0009 (7)	0.0012 (6)
O4	0.0741 (14)	0.0393 (10)	0.0324 (10)	−0.0108 (9)	−0.0107 (9)	0.0109 (8)
O1W	0.0515 (11)	0.0420 (10)	0.0285 (9)	−0.0172 (8)	−0.0077 (8)	0.0020 (8)
O2W	0.0443 (11)	0.0399 (10)	0.0305 (9)	−0.0111 (8)	0.0032 (8)	−0.0105 (7)
O3W	0.0438 (11)	0.0461 (11)	0.0454 (11)	−0.0136 (9)	−0.0159 (9)	0.0105 (9)
O4W	0.0417 (11)	0.0376 (10)	0.0598 (13)	−0.0030 (9)	−0.0008 (10)	−0.0093 (9)
N1	0.0460 (12)	0.0244 (9)	0.0283 (10)	0.0029 (8)	0.0019 (9)	0.0024 (7)
C1	0.0442 (14)	0.0258 (11)	0.0322 (13)	−0.0020 (10)	−0.0042 (10)	0.0034 (9)
C2	0.0248 (19)	0.0265 (16)	0.0328 (18)	0.0014 (13)	0.0023 (14)	0.0028 (12)
C3	0.112 (6)	0.033 (2)	0.042 (3)	0.013 (3)	−0.020 (4)	−0.0076 (19)
C2'	0.049 (7)	0.036 (5)	0.038 (5)	0.004 (5)	0.011 (5)	0.004 (4)
C3'	0.057 (7)	0.037 (6)	0.036 (6)	0.007 (6)	0.007 (6)	0.010 (4)
C4	0.0437 (14)	0.0333 (12)	0.0236 (11)	0.0018 (10)	0.0034 (10)	−0.0006 (9)
C5	0.0312 (11)	0.0268 (10)	0.0257 (11)	−0.0058 (9)	−0.0038 (9)	0.0032 (8)
C6	0.0356 (12)	0.0342 (12)	0.0249 (11)	−0.0065 (10)	−0.0016 (9)	−0.0012 (9)
C7	0.0414 (13)	0.0326 (12)	0.0241 (11)	−0.0100 (10)	−0.0075 (10)	0.0047 (9)
C8	0.0507 (15)	0.0253 (11)	0.0326 (13)	−0.0046 (10)	−0.0068 (11)	0.0051 (9)
C9	0.0520 (15)	0.0263 (11)	0.0288 (12)	−0.0002 (10)	−0.0018 (11)	−0.0005 (9)
C10	0.0313 (11)	0.0268 (10)	0.0248 (11)	−0.0050 (9)	−0.0052 (9)	0.0008 (8)
C11	0.0500 (15)	0.0383 (13)	0.0281 (12)	−0.0132 (11)	−0.0068 (10)	0.0045 (10)

Geometric parameters (Å, º)

Ni1—N1	1.999 (2)	C2—C3	1.528 (6)
Ni1—O3	2.0149 (16)	C2—H2	0.9800
Ni1—O2W	2.0450 (19)	C3—H3A	0.9600
Ni1—O1	2.0455 (16)	C3—H3B	0.9600
Ni1—O3W	2.053 (2)	C3—H3C	0.9600
Ni1—O1W	2.1063 (19)	C2'—C3'	1.512 (9)
C1—O1	1.250 (3)	C2'—H2'	0.9800
C1—O2	1.245 (3)	C3'—H3'1	0.9600
O3—C10	1.302 (3)	C3'—H3'2	0.9600
O4—C11	1.212 (3)	C3'—H3'3	0.9600
O1W—H1W1	0.845 (10)	C4—C5	1.449 (3)
O1W—H1W2	0.842 (10)	C4—H4	0.9300
O2W—H2W1	0.845 (10)	C5—C6	1.397 (3)
O2W—H2W2	0.845 (10)	C5—C10	1.421 (3)
O3W—H3W1	0.840 (10)	C6—C7	1.382 (3)
O3W—H3W2	0.847 (10)	C6—H6	0.9300
O4W—H4W1	0.841 (10)	C7—C8	1.390 (4)
O4W—H4W2	0.844 (10)	C7—C11	1.454 (3)
N1—C4	1.272 (3)	C8—C9	1.368 (3)
N1—C2	1.485 (4)	C8—H8	0.9300
N1—C2'	1.516 (8)	C9—C10	1.422 (3)
C1—C2	1.538 (4)	C9—H9	0.9300
C1—C2'	1.558 (8)	C11—H11	0.9300
N1—Ni1—O3	91.55 (7)	C1—C2—H2	110.1
N1—Ni1—O2W	175.02 (7)	C2—C3—H3A	109.5
O3—Ni1—O2W	93.10 (7)	C2—C3—H3B	109.5
N1—Ni1—O1	81.70 (7)	H3A—C3—H3B	109.5
O3—Ni1—O1	173.25 (6)	C2—C3—H3C	109.5
O2W—Ni1—O1	93.65 (7)	H3A—C3—H3C	109.5
N1—Ni1—O3W	95.22 (9)	H3B—C3—H3C	109.5
O3—Ni1—O3W	89.33 (8)	C3'—C2'—N1	114.9 (11)
O2W—Ni1—O3W	86.63 (8)	C3'—C2'—C1	113.1 (11)
O1—Ni1—O3W	91.04 (8)	N1—C2'—C1	105.0 (6)
N1—Ni1—O1W	93.73 (9)	C3'—C2'—H2'	107.8
O3—Ni1—O1W	91.45 (7)	N1—C2'—H2'	107.8
O2W—Ni1—O1W	84.37 (8)	C1—C2'—H2'	107.8
O1—Ni1—O1W	89.24 (7)	C2'—C3'—H3'1	109.5
O3W—Ni1—O1W	170.99 (8)	C2'—C3'—H3'2	109.5
C1—O1—Ni1	114.98 (14)	H3'1—C3'—H3'2	109.5
C10—O3—Ni1	126.69 (14)	C2'—C3'—H3'3	109.5
Ni1—O1W—H1W1	114 (2)	H3'1—C3'—H3'3	109.5
Ni1—O1W—H1W2	119 (3)	H3'2—C3'—H3'3	109.5
H1W1—O1W—H1W2	110 (3)	N1—C4—C5	125.9 (2)
Ni1—O2W—H2W1	124 (3)	N1—C4—H4	117.0
Ni1—O2W—H2W2	116 (3)	C5—C4—H4	117.0
H2W1—O2W—H2W2	104 (4)	C6—C5—C10	118.8 (2)
Ni1—O3W—H3W1	123 (2)	C6—C5—C4	116.7 (2)
Ni1—O3W—H3W2	122 (2)	C10—C5—C4	124.6 (2)
H3W1—O3W—H3W2	96 (3)	C7—C6—C5	122.4 (2)
H4W1—O4W—H4W2	103 (3)	C7—C6—H6	118.8
C4—N1—C2	118.8 (2)	C5—C6—H6	118.8
C4—N1—C2'	121.0 (3)	C6—C7—C8	118.9 (2)
C2—N1—C2'	29.3 (5)	C6—C7—C11	118.7 (2)
C4—N1—Ni1	126.63 (17)	C8—C7—C11	122.3 (2)
C2—N1—Ni1	114.18 (17)	C9—C8—C7	120.5 (2)
C2'—N1—Ni1	107.9 (4)	C9—C8—H8	119.8
O2—C1—O1	123.8 (2)	C7—C8—H8	119.8
O2—C1—C2	116.6 (2)	C8—C9—C10	121.8 (2)
O1—C1—C2	119.3 (2)	C8—C9—H9	119.1
O2—C1—C2'	116.3 (3)	C10—C9—H9	119.1
O1—C1—C2'	115.2 (4)	O3—C10—C5	124.49 (19)
C2—C1—C2'	28.4 (5)	O3—C10—C9	117.9 (2)
N1—C2—C3	109.6 (4)	C5—C10—C9	117.6 (2)
N1—C2—C1	107.6 (2)	O4—C11—C7	124.9 (3)
C3—C2—C1	109.3 (4)	O4—C11—H11	117.6
N1—C2—H2	110.1	C7—C11—H11	117.6
C3—C2—H2	110.1
N1—Ni1—O1—C1	−5.22 (18)	C4—N1—C2'—C3'	37.6 (17)
O2W—Ni1—O1—C1	172.96 (19)	C2—N1—C2'—C3'	−57.0 (15)
O3W—Ni1—O1—C1	−100.35 (19)	Ni1—N1—C2'—C3'	−164.6 (12)
O1W—Ni1—O1—C1	88.66 (19)	C4—N1—C2'—C1	162.6 (5)
N1—Ni1—O3—C10	−4.48 (19)	C2—N1—C2'—C1	68.0 (8)
O2W—Ni1—O3—C10	177.31 (19)	Ni1—N1—C2'—C1	−39.7 (9)
O3W—Ni1—O3—C10	90.72 (19)	O2—C1—C2'—C3'	−38.8 (16)
O1W—Ni1—O3—C10	−98.26 (19)	O1—C1—C2'—C3'	164.5 (11)
O3—Ni1—N1—C4	2.1 (2)	C2—C1—C2'—C3'	58.9 (15)
O1—Ni1—N1—C4	−177.6 (3)	O2—C1—C2'—N1	−164.9 (5)
O3W—Ni1—N1—C4	−87.3 (2)	O1—C1—C2'—N1	38.4 (10)
O1W—Ni1—N1—C4	93.7 (2)	C2—C1—C2'—N1	−67.1 (8)
O3—Ni1—N1—C2	175.2 (2)	C2—N1—C4—C5	−172.8 (3)
O1—Ni1—N1—C2	−4.6 (2)	C2'—N1—C4—C5	153.3 (7)
O3W—Ni1—N1—C2	85.7 (2)	Ni1—N1—C4—C5	0.0 (4)
O1W—Ni1—N1—C2	−93.3 (2)	N1—C4—C5—C6	179.8 (3)
O3—Ni1—N1—C2'	−154.0 (6)	N1—C4—C5—C10	−1.1 (4)
O1—Ni1—N1—C2'	26.2 (6)	C10—C5—C6—C7	0.9 (4)
O3W—Ni1—N1—C2'	116.5 (6)	C4—C5—C6—C7	−179.9 (2)
O1W—Ni1—N1—C2'	−62.5 (6)	C5—C6—C7—C8	−0.1 (4)
Ni1—O1—C1—O2	−172.5 (2)	C5—C6—C7—C11	−177.7 (2)
Ni1—O1—C1—C2	14.0 (3)	C6—C7—C8—C9	−0.6 (4)
Ni1—O1—C1—C2'	−17.7 (7)	C11—C7—C8—C9	176.9 (2)
C4—N1—C2—C3	−56.1 (6)	C7—C8—C9—C10	0.4 (4)
C2'—N1—C2—C3	46.6 (8)	Ni1—O3—C10—C5	4.8 (3)
Ni1—N1—C2—C3	130.3 (4)	Ni1—O3—C10—C9	−176.50 (17)
C4—N1—C2—C1	−174.9 (3)	C6—C5—C10—O3	177.6 (2)
C2'—N1—C2—C1	−72.2 (6)	C4—C5—C10—O3	−1.5 (4)
Ni1—N1—C2—C1	11.5 (4)	C6—C5—C10—C9	−1.1 (3)
O2—C1—C2—N1	169.1 (3)	C4—C5—C10—C9	179.8 (2)
O1—C1—C2—N1	−16.9 (4)	C8—C9—C10—O3	−178.3 (2)
C2'—C1—C2—N1	72.4 (6)	C8—C9—C10—C5	0.5 (4)
O2—C1—C2—C3	50.2 (5)	C6—C7—C11—O4	−179.7 (3)
O1—C1—C2—C3	−135.9 (4)	C8—C7—C11—O4	2.8 (4)
C2'—C1—C2—C3	−46.5 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O1^i	0.85 (1)	1.95 (1)	2.784 (2)	170 (3)
O1w—H1w2···O4^ii	0.84 (1)	1.97 (2)	2.786 (3)	162 (4)
O2w—H2w1···O3^iii	0.85 (1)	1.93 (1)	2.769 (2)	173 (4)
O2w—H2w2···O2^i	0.85 (1)	2.19 (2)	2.937 (3)	147 (3)
O3w—H3w1···O2^iv	0.84 (1)	1.95 (1)	2.753 (3)	161 (3)
O3w—H3w2···O4w^v	0.85 (1)	1.85 (1)	2.689 (3)	171 (4)
O4w—H4w1···O2	0.84 (1)	1.92 (1)	2.741 (3)	166 (3)
O4w—H4w2···O3^vi	0.84 (1)	2.11 (2)	2.929 (3)	165 (4)

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