(Oxalato-κ²O,O′)(1,10-phenanthroline-κ²N,N′)­palladium(II) monohydrate

In the title compound, [Pd(C₂O₄)(C₁₂H₈N₂)]·H₂O, the Pd^II atom is coordinated by two N atoms of 1,10-phenanthroline and two O atoms of an oxalate ligand, with cis-square-planar geometry. The oxalate C—C bonds are elongated compared with oxalic acid. The asymmetric unit contains two complex mol­ecules and two mol­ecules of water.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.025
• wR factor = 0.073
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C6     -   C7      ..      10.30 su
PLAT369_ALERT_2_B Long   C(sp2)-C(sp2) Bond  C13    -   C14    ...       1.57 Ang.
PLAT369_ALERT_2_B Long   C(sp2)-C(sp2) Bond  C27    -   C28    ...       1.57 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.43
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7     -   C9      ..       6.72 su
PLAT335_ALERT_2_C Large Benzene C-C Range          C4     -C6            0.16 Ang.

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   6 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure.

(Oxalato-κ²O,O')(1,10-phenanthroline-κ²N,N')palladium(II) monohydrate

Crystal data

[Pd(C2O4)(C12H8N2)]·H2O	Z = 4
Mr = 392.66	F(000) = 776.00
Triclinic, P_1	Dx = 1.958 Mg m^−3
Hall symbol: -p_1	Mo Kα radiation, λ = 0.7107 Å
a = 7.028 (7) Å	Cell parameters from 11758 reflections
b = 11.527 (15) Å	θ = 3.0–27.5°
c = 17.85 (2) Å	µ = 1.42 mm^−1
α = 72.36 (4)°	T = 296 K
β = 88.96 (3)°	Needle, brown
γ = 75.55 (4)°	0.50 × 0.10 × 0.10 mm
V = 1332 (2) Å^3

Data collection

Rigaku RAXIS-RAPID diffractometer	5030 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.013
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→8
Tmin = 0.601, Tmax = 0.867	k = −14→14
12903 measured reflections	l = −22→23
5903 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.025	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 0.4089P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.073	(Δ/σ)max = 0.002
S = 1.13	Δρmax = 0.85 e Å^−3
5903 reflections	Δρmin = −0.35 e Å^−3
410 parameters

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Pd1	0.29052 (3)	0.96695 (2)	0.01017 (1)	0.02967 (7)
Pd2	0.25067 (3)	0.44628 (2)	0.50412 (1)	0.03532 (7)
O1	0.2032 (3)	1.0427 (2)	0.0966 (1)	0.0404 (4)
O2	0.0069 (3)	1.2173 (2)	0.1115 (1)	0.0526 (5)
O3	0.1221 (3)	1.1281 (2)	−0.0591 (1)	0.0365 (4)
O4	−0.0838 (3)	1.3025 (2)	−0.0506 (1)	0.0505 (5)
O5	0.2725 (3)	0.2751 (2)	0.4946 (1)	0.0470 (5)
O6	0.3461 (4)	0.0759 (2)	0.5692 (1)	0.0625 (6)
O7	0.3096 (3)	0.3535 (2)	0.6180 (1)	0.0468 (5)
O8	0.3753 (4)	0.1583 (2)	0.6992 (1)	0.0671 (7)
O9	0.3474 (4)	0.1587 (3)	0.3694 (1)	0.0675 (7)
O10	0.0169 (4)	0.2807 (3)	0.2552 (1)	0.0807 (9)
N1	0.3719 (3)	0.8897 (2)	−0.0760 (1)	0.0327 (4)
N2	0.4607 (3)	0.8015 (2)	0.0768 (1)	0.0328 (4)
N3	0.2298 (3)	0.6172 (2)	0.5135 (1)	0.0377 (5)
N4	0.1944 (3)	0.5453 (2)	0.3896 (1)	0.0402 (5)
C1	0.3293 (4)	0.9416 (3)	−0.1529 (1)	0.0410 (6)
C2	0.3948 (5)	0.8740 (3)	−0.2053 (2)	0.0506 (7)
C3	0.5074 (5)	0.7531 (3)	−0.1789 (2)	0.0491 (7)
C4	0.5606 (4)	0.6963 (3)	−0.0973 (2)	0.0396 (6)
C5	0.4866 (3)	0.7690 (2)	−0.0482 (1)	0.0323 (5)
C6	0.6841 (4)	0.5728 (3)	−0.0619 (2)	0.0478 (7)
C7	0.7349 (4)	0.5209 (3)	0.0158 (2)	0.0411 (6)
C8	0.5352 (3)	0.7217 (2)	0.0340 (1)	0.0322 (5)
C9	0.6573 (4)	0.6008 (2)	0.0679 (2)	0.0383 (6)
C10	0.7015 (4)	0.5633 (3)	0.1499 (2)	0.0481 (7)
C11	0.6299 (5)	0.6445 (3)	0.1908 (2)	0.0499 (7)
C12	0.5090 (4)	0.7647 (3)	0.1534 (2)	0.0410 (6)
C13	0.0820 (4)	1.1523 (3)	0.0709 (1)	0.0358 (5)
C14	0.0315 (4)	1.2020 (2)	−0.0203 (1)	0.0343 (5)
C15	0.2447 (5)	0.6491 (3)	0.5791 (2)	0.0473 (7)
C16	0.2314 (5)	0.7733 (3)	0.5753 (2)	0.0567 (8)
C17	0.1997 (5)	0.8653 (3)	0.5047 (2)	0.0550 (8)
C18	0.1769 (4)	0.8363 (3)	0.4349 (2)	0.0459 (6)
C19	0.1945 (4)	0.7092 (3)	0.4431 (1)	0.0369 (5)
C20	0.1380 (5)	0.9246 (3)	0.3571 (2)	0.0587 (8)
C21	0.1172 (5)	0.8873 (3)	0.2930 (2)	0.0589 (8)
C22	0.1752 (4)	0.6700 (3)	0.3754 (1)	0.0383 (6)
C23	0.1337 (4)	0.7586 (3)	0.3006 (2)	0.0482 (7)
C24	0.1109 (4)	0.7119 (4)	0.2374 (2)	0.0569 (9)
C25	0.1301 (5)	0.5864 (4)	0.2524 (2)	0.0576 (8)
C26	0.1733 (4)	0.5037 (3)	0.3283 (2)	0.0501 (7)
C27	0.3190 (4)	0.1860 (3)	0.5618 (2)	0.0424 (6)
C28	0.3377 (4)	0.2329 (3)	0.6344 (2)	0.0430 (6)
H1	0.2546	1.0246	−0.1722	0.049*
H2	0.3613	0.9118	−0.2589	0.061*
H3	0.5490	0.7082	−0.2141	0.059*
H4	0.7331	0.5246	−0.0948	0.057*
H5	0.8144	0.4395	0.0362	0.049*
H6	0.7797	0.4832	0.1757	0.058*
H7	0.6614	0.6201	0.2447	0.060*
H8	0.4621	0.8193	0.1826	0.049*
H9	0.2643	0.5871	0.6279	0.057*
H10	0.2444	0.7933	0.6214	0.068*
H11	0.1930	0.9479	0.5026	0.066*
H12	0.1267	1.0094	0.3503	0.070*
H13	0.0919	0.9469	0.2433	0.071*
H14	0.0830	0.7665	0.1863	0.068*
H15	0.1141	0.5556	0.2110	0.069*
H16	0.1879	0.4182	0.3369	0.060*
H17	0.3334	0.1862	0.4133	0.101*
H18	0.4323	0.0801	0.3827	0.101*
H19	0.1286	0.2298	0.2860	0.121*
H20	0.0051	0.2514	0.2135	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.0308 (1)	0.0255 (1)	0.0312 (1)	−0.00342 (7)	0.00136 (7)	−0.00950 (7)
Pd2	0.0402 (1)	0.0336 (1)	0.0305 (1)	−0.00583 (8)	0.00114 (8)	−0.01032 (8)
O1	0.045 (1)	0.039 (1)	0.0351 (9)	−0.0027 (8)	−0.0002 (8)	−0.0150 (8)
O2	0.055 (1)	0.056 (1)	0.051 (1)	−0.003 (1)	0.005 (1)	−0.033 (1)
O3	0.0421 (9)	0.0285 (9)	0.0326 (9)	0.0015 (7)	0.0009 (7)	−0.0090 (7)
O4	0.055 (1)	0.035 (1)	0.054 (1)	0.0048 (9)	0.000 (1)	−0.0161 (9)
O5	0.062 (1)	0.041 (1)	0.039 (1)	−0.0081 (9)	0.0006 (9)	−0.0178 (9)
O6	0.074 (2)	0.038 (1)	0.074 (2)	−0.005 (1)	−0.005 (1)	−0.022 (1)
O7	0.066 (1)	0.037 (1)	0.0332 (9)	−0.0079 (9)	−0.0011 (9)	−0.0096 (8)
O8	0.097 (2)	0.048 (1)	0.044 (1)	−0.012 (1)	−0.009 (1)	−0.001 (1)
O9	0.082 (2)	0.064 (2)	0.053 (1)	−0.001 (1)	−0.014 (1)	−0.026 (1)
O10	0.092 (2)	0.080 (2)	0.055 (2)	0.017 (2)	−0.013 (1)	−0.031 (1)
N1	0.033 (1)	0.029 (1)	0.035 (1)	−0.0060 (8)	0.0030 (9)	−0.0112 (9)
N2	0.031 (1)	0.029 (1)	0.037 (1)	−0.0044 (8)	−0.0007 (8)	−0.0091 (9)
N3	0.039 (1)	0.038 (1)	0.035 (1)	−0.0097 (9)	0.0026 (9)	−0.0110 (9)
N4	0.040 (1)	0.047 (1)	0.033 (1)	−0.008 (1)	0.0013 (9)	−0.013 (1)
C1	0.046 (1)	0.036 (1)	0.036 (1)	−0.005 (1)	0.002 (1)	−0.008 (1)
C2	0.063 (2)	0.050 (2)	0.037 (1)	−0.007 (1)	0.006 (1)	−0.015 (1)
C3	0.059 (2)	0.047 (2)	0.046 (2)	−0.011 (1)	0.015 (1)	−0.025 (1)
C4	0.037 (1)	0.036 (1)	0.049 (1)	−0.009 (1)	0.010 (1)	−0.019 (1)
C5	0.032 (1)	0.028 (1)	0.037 (1)	−0.0080 (9)	0.004 (1)	−0.010 (1)
C6	0.047 (2)	0.036 (2)	0.064 (2)	−0.007 (1)	0.014 (1)	−0.025 (1)
C7	0.027 (1)	0.045 (2)	0.045 (1)	−0.010 (1)	0.001 (1)	−0.004 (1)
C8	0.029 (1)	0.028 (1)	0.038 (1)	−0.0062 (9)	0.002 (1)	−0.008 (1)
C9	0.031 (1)	0.029 (1)	0.051 (2)	−0.004 (1)	−0.001 (1)	−0.009 (1)
C10	0.044 (1)	0.035 (2)	0.051 (2)	−0.002 (1)	−0.008 (1)	0.000 (1)
C11	0.053 (2)	0.046 (2)	0.040 (1)	−0.006 (1)	−0.010 (1)	−0.004 (1)
C12	0.042 (1)	0.040 (2)	0.040 (1)	−0.008 (1)	−0.000 (1)	−0.013 (1)
C13	0.034 (1)	0.036 (1)	0.042 (1)	−0.011 (1)	0.008 (1)	−0.018 (1)
C14	0.033 (1)	0.027 (1)	0.043 (1)	−0.007 (1)	0.003 (1)	−0.012 (1)
C15	0.056 (2)	0.049 (2)	0.039 (1)	−0.014 (1)	0.003 (1)	−0.017 (1)
C16	0.060 (2)	0.061 (2)	0.062 (2)	−0.018 (2)	0.002 (2)	−0.035 (2)
C17	0.054 (2)	0.043 (2)	0.074 (2)	−0.015 (1)	0.006 (2)	−0.024 (2)
C18	0.037 (1)	0.039 (2)	0.059 (2)	−0.011 (1)	0.003 (1)	−0.011 (1)
C19	0.031 (1)	0.039 (1)	0.038 (1)	−0.008 (1)	0.002 (1)	−0.009 (1)
C20	0.054 (2)	0.039 (2)	0.072 (2)	−0.014 (1)	0.002 (2)	0.001 (2)
C21	0.052 (2)	0.054 (2)	0.055 (2)	−0.014 (2)	−0.001 (1)	0.008 (2)
C22	0.032 (1)	0.045 (2)	0.034 (1)	−0.009 (1)	0.003 (1)	−0.006 (1)
C23	0.036 (1)	0.058 (2)	0.038 (1)	−0.009 (1)	0.001 (1)	0.001 (1)
C24	0.045 (2)	0.081 (3)	0.031 (1)	−0.010 (2)	−0.001 (1)	−0.004 (1)
C25	0.054 (2)	0.083 (3)	0.037 (1)	−0.013 (2)	−0.000 (1)	−0.022 (2)
C26	0.054 (2)	0.060 (2)	0.040 (1)	−0.013 (1)	0.001 (1)	−0.022 (1)
C27	0.040 (1)	0.038 (2)	0.047 (1)	−0.006 (1)	0.003 (1)	−0.014 (1)
C28	0.043 (1)	0.042 (2)	0.039 (1)	−0.005 (1)	0.002 (1)	−0.010 (1)

Geometric parameters (Å, º)

Pd1—O1	2.009 (2)	C4—C6	1.428 (3)
Pd1—O3	1.986 (3)	C5—C8	1.416 (3)
Pd1—N1	2.007 (2)	C6—C7	1.348 (4)
Pd1—N2	2.006 (2)	C6—H4	0.93
Pd2—O5	1.999 (2)	C7—C9	1.503 (4)
Pd2—O7	1.985 (2)	C7—H5	0.93
Pd2—N3	1.997 (3)	C8—C9	1.398 (3)
Pd2—N4	2.007 (2)	C9—C10	1.412 (4)
O1—C13	1.287 (3)	C10—C11	1.351 (5)
O2—C13	1.217 (4)	C10—H6	0.93
O3—C14	1.295 (3)	C11—C12	1.400 (4)
O4—C14	1.208 (3)	C11—H7	0.93
O5—C27	1.304 (3)	C12—H8	0.93
O6—C27	1.200 (4)	C13—C14	1.569 (4)
O7—C28	1.295 (4)	C15—C16	1.393 (5)
O8—C28	1.201 (3)	C15—H9	0.93
O9—H17	0.92	C16—C17	1.358 (4)
O9—H18	0.91	C16—H10	0.93
O10—H19	0.92	C17—C18	1.406 (5)
O10—H20	0.92	C17—H11	0.93
N1—C1	1.327 (3)	C18—C19	1.401 (5)
N1—C5	1.367 (3)	C18—C20	1.434 (4)
N2—C8	1.369 (4)	C19—C22	1.431 (4)
N2—C12	1.326 (3)	C20—C21	1.360 (6)
N3—C15	1.342 (4)	C20—H12	0.93
N3—C19	1.355 (3)	C21—C23	1.423 (5)
N4—C22	1.354 (4)	C21—H13	0.93
N4—C26	1.345 (5)	C22—C23	1.396 (3)
C1—C2	1.393 (5)	C23—C24	1.416 (5)
C1—H1	0.93	C24—C25	1.361 (6)
C2—C3	1.362 (4)	C24—H14	0.93
C2—H2	0.93	C25—C26	1.387 (4)
C3—C4	1.417 (4)	C25—H15	0.93
C3—H3	0.93	C26—H16	0.93
C4—C5	1.397 (4)	C27—C28	1.566 (5)
O1—Pd1—O3	83.93 (7)	C10—C9—C7	124.5 (2)
O1—Pd1—N1	178.60 (9)	C11—C10—C9	119.7 (2)
O1—Pd1—N2	98.12 (8)	C11—C10—H6	120.2
O3—Pd1—N1	95.97 (7)	H6—C10—C9	120.2
O3—Pd1—N2	177.87 (9)	C12—C11—C10	121.1 (3)
N1—Pd1—N2	81.96 (8)	C12—C11—H7	119.7
O5—Pd2—O7	83.80 (9)	H7—C11—C10	119.5
O5—Pd2—N3	179.80 (9)	H8—C12—N2	119.7
O5—Pd2—N4	98.2 (1)	H8—C12—C11	119.7
O7—Pd2—N3	96.23 (9)	C14—C13—O1	115.3 (2)
O7—Pd2—N4	177.9 (1)	C14—C13—O2	119.4 (2)
N3—Pd2—N4	81.8 (1)	O1—C13—O2	125.3 (2)
C13—O1—Pd1	112.5 (2)	C13—C14—O3	115.2 (2)
C14—O3—Pd1	112.9 (1)	C13—C14—O4	121.0 (3)
C27—O5—Pd2	112.9 (2)	O3—C14—O4	123.8 (2)
C28—O7—Pd2	113.4 (2)	C16—C15—N3	121.1 (3)
H17—O9—H18	108.9	C16—C15—H9	119.5
H19—O10—H20	108.3	H9—C15—N3	119.5
C1—N1—Pd1	128.1 (2)	C17—C16—C15	120.3 (4)
C1—N1—C5	119.2 (2)	C17—C16—H10	119.9
C5—N1—Pd1	112.7 (2)	H10—C16—C15	119.9
C8—N2—Pd1	112.5 (1)	C18—C17—C16	120.3 (3)
C8—N2—C12	119.2 (2)	C18—C17—H11	119.8
C12—N2—Pd1	128.3 (2)	H11—C17—C16	119.8
C15—N3—Pd2	128.2 (2)	C19—C18—C17	116.2 (2)
C15—N3—C19	118.7 (3)	C19—C18—C20	117.9 (3)
C19—N3—Pd2	113.1 (2)	C20—C18—C17	125.9 (3)
C22—N4—Pd2	112.9 (2)	C22—C19—N3	116.2 (3)
C22—N4—C26	118.4 (2)	C22—C19—C18	120.4 (2)
C26—N4—Pd2	128.7 (2)	C21—C20—C18	121.5 (3)
C2—C1—N1	121.1 (2)	C21—C20—H12	119.2
C2—C1—H1	119.4573	H12—C20—C18	119.2
H1—C1—N1	119.5	C23—C21—H13	119.5
C3—C2—C1	120.7 (3)	C23—C21—C20	121.1 (3)
C3—C2—H2	119.6	H13—C21—C20	119.4
H2—C2—C1	119.6	C23—C22—N4	123.8 (3)
C4—C3—C2	119.5 (3)	C23—C22—C19	120.3 (3)
C4—C3—H3	120.2	C24—C23—C22	116.4 (3)
H3—C3—C2	120.2	C24—C23—C21	124.9 (3)
C5—C4—C3	116.5 (2)	C25—C24—H14	120.3
C5—C4—C6	117.9 (2)	C25—C24—C23	119.3 (3)
C6—C4—C3	125.6 (3)	H14—C24—C23	120.3
C8—C5—N1	116.3 (2)	C26—C25—H15	119.5
C8—C5—C4	120.8 (2)	C26—C25—C24	121.1 (4)
C7—C6—C4	124.6 (3)	H15—C25—C24	119.5
C7—C6—H4	117.7	H16—C26—N4	119.5
H4—C6—C4	117.7	H16—C26—C25	119.5
C9—C7—C6	117.0 (2)	C28—C27—O5	114.7 (3)
C9—C7—H5	121.5	C28—C27—O6	121.3 (2)
H5—C7—C6	121.5	O5—C27—O6	124.0 (3)
C9—C8—N2	122.7 (2)	C27—C28—O7	115.1 (2)
C9—C8—C5	120.7 (3)	C27—C28—O8	119.9 (3)
C10—C9—C8	116.6 (3)	O7—C28—O8	125.0 (3)
O3—Pd1—O1—C13	1.6 (2)	C6—C7—C9—C8	1.3 (4)
O1—Pd1—O3—C14	−2.6 (2)	N2—C8—C9—C7	−178.9 (3)
O1—Pd1—N2—C8	176.0 (2)	C5—C8—C9—C7	−0.6 (4)
O7—Pd2—O5—C27	−2.2 (2)	C7—C9—C10—C11	177.4 (3)
O5—Pd2—O7—C28	1.2 (2)	C9—C10—C11—C12	1.2 (5)
O5—Pd2—N4—C22	−178.6 (2)	C10—C11—C12—N2	0.5 (5)
Pd1—O1—C13—O2	179.5 (3)	O1—C13—C14—O3	−1.8 (4)
Pd1—O3—C14—O4	−177.2 (2)	O1—C13—C14—O4	178.4 (3)
Pd1—O3—C14—C13	3.0 (3)	O2—C13—C14—O3	178.3 (3)
Pd2—O5—C27—O6	−177.4 (3)	O2—C13—C14—O4	−1.5 (4)
Pd2—O7—C28—O8	180.0 (2)	N3—C15—C16—C17	1.1 (5)
Pd2—O7—C28—C27	−0.1 (3)	C15—C16—C17—C18	1.0 (5)
Pd1—N1—C1—C2	−178.8 (3)	C16—C17—C18—C19	−1.7 (4)
Pd1—N1—C5—C4	180.0 (2)	C17—C18—C19—N3	0.5 (4)
Pd1—N2—C8—C5	1.9 (3)	C17—C18—C20—C21	−179.6 (3)
Pd1—N2—C12—C11	179.7 (2)	N3—C19—C22—N4	−0.0 (3)
Pd2—N3—C15—C16	178.4 (2)	C18—C19—C22—N4	−180.0 (2)
Pd2—N3—C19—C18	−179.1 (2)	C18—C20—C21—C23	−0.1 (4)
Pd2—N4—C22—C19	−1.0 (3)	C20—C21—C23—C22	−1.1 (5)
Pd2—N4—C26—C25	178.6 (2)	N4—C22—C23—C21	−179.9 (3)
N1—C1—C2—C3	−1.1 (5)	C19—C22—C23—C21	1.9 (4)
C1—C2—C3—C4	−0.9 (5)	C21—C23—C24—C25	180.0 (3)
C2—C3—C4—C5	2.0 (5)	C23—C24—C25—C26	−0.5 (5)
C3—C4—C5—N1	−1.3 (4)	C24—C25—C26—N4	1.0 (5)
C3—C4—C6—C7	179.2 (3)	O5—C27—C28—O7	−1.7 (4)
N1—C5—C8—N2	0.6 (4)	O5—C27—C28—O8	178.2 (3)
C4—C5—C8—N2	177.9 (2)	O6—C27—C28—O7	178.3 (3)
C4—C6—C7—C9	−1.0 (5)	O6—C27—C28—O8	−1.8 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H17···O5	0.92	2.00	2.915 (4)	169
O9—H18···O6^i	0.91	2.03	2.921 (3)	165
O10—H19···O9	0.92	1.99	2.887 (3)	163
O10—H20···O2^ii	0.92	1.97	2.879 (4)	168

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