trans-Diaqua­bis(5,5-diphenyl­hydantoinato-κN³)bis­(hexa­methyl­enetetra­amine-κN)cobalt(II) hemihydrate

In the title complex, [Co(C₁₅H₁₁N₂O₂)₂(C₆H₁₂N₄)₂(H₂O)₂]·0.5H₂O, the Co^II ion lies on an inversion centre and is coordinated in a distorted octa­hedral geometry. There are intra- and inter­molecular N—H...O, O—H...O and O—H...N hydrogen bonds, forming a two-dimensional network in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.043
• wR factor = 0.108
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT415_ALERT_2_C Short Inter D-H..H-X       H14    ..  H24     ..       2.11 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H23    ..  H24     ..       2.13 Ang.

   0 ALERT level A = In general: serious problem
   0 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
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

trans-Diaquabis(5,5-diphenylhydantoinato-κN³)bis(hexamethylenetetraamine- κN)cobalt(II) hemihydrate

Crystal data

[Co(C15H11N2O2)2(C6H12N4)2(H2O)2]·0.5H2O	Z = 1
Mr = 886.88	F(000) = 466
Triclinic, P1	Dx = 1.454 Mg m^−3
Hall symbol: -P 1	Melting point: 640 K
a = 8.947 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.183 (4) Å	Cell parameters from 2021 reflections
c = 11.620 (4) Å	θ = 2.3–25.1°
α = 79.516 (4)°	µ = 0.49 mm^−1
β = 76.753 (5)°	T = 298 K
γ = 88.532 (4)°	Block, orange
V = 1013.2 (6) Å^3	0.21 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3523 independent reflections
Radiation source: fine-focus sealed tube	2657 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.904, Tmax = 0.930	k = −12→12
5327 measured reflections	l = −7→13

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0383P)^2 + 0.8777P] where P = (Fo^2 + 2Fc^2)/3
3523 reflections	(Δ/σ)max < 0.001
286 parameters	Δρmax = 0.41 e Å^−3
3 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)
Co1	0.5000	0.5000	0.5000	0.03026 (18)
N1	0.5853 (3)	0.8751 (2)	0.5992 (2)	0.0317 (6)
H1	0.5892	0.9609	0.5826	0.038*
N2	0.5571 (3)	0.6635 (2)	0.57365 (19)	0.0265 (5)
N3	0.3032 (3)	0.4325 (2)	0.6735 (2)	0.0329 (6)
N4	0.1209 (3)	0.5099 (3)	0.8408 (3)	0.0461 (7)
N5	0.2242 (3)	0.2866 (3)	0.8714 (2)	0.0488 (7)
N6	0.0394 (3)	0.3388 (3)	0.7455 (3)	0.0572 (8)
O1	0.4711 (2)	0.84162 (18)	0.44968 (17)	0.0346 (5)
O2	0.6668 (2)	0.55291 (18)	0.72441 (18)	0.0366 (5)
O3	0.3329 (2)	0.61456 (19)	0.43152 (18)	0.0379 (5)
H22	0.3782	0.6846	0.3873	0.045*
H23	0.2655	0.5890	0.3991	0.045*
O4	0.1754 (16)	0.8335 (14)	0.3190 (14)	0.136 (6)	0.25
H24	0.1402	0.7693	0.3760	0.163*	0.25
H25	0.0998	0.8457	0.2856	0.163*	0.25
C1	0.5328 (3)	0.7982 (3)	0.5344 (2)	0.0269 (6)
C2	0.6227 (3)	0.6551 (3)	0.6684 (3)	0.0283 (6)
C3	0.6352 (3)	0.7961 (3)	0.7010 (3)	0.0295 (6)
C4	0.5219 (3)	0.8077 (3)	0.8196 (3)	0.0312 (7)
C5	0.4534 (4)	0.9289 (3)	0.8347 (3)	0.0454 (8)
H5	0.4740	1.0014	0.7717	0.055*
C6	0.3552 (4)	0.9438 (4)	0.9418 (3)	0.0562 (10)
H6	0.3101	1.0258	0.9502	0.067*
C7	0.3240 (4)	0.8379 (4)	1.0359 (3)	0.0571 (10)
H7	0.2584	0.8482	1.1083	0.068*
C8	0.3897 (4)	0.7171 (4)	1.0229 (3)	0.0500 (9)
H8	0.3676	0.6449	1.0861	0.060*
C9	0.4889 (4)	0.7022 (3)	0.9159 (3)	0.0424 (8)
H9	0.5342	0.6200	0.9084	0.051*
C10	0.8017 (3)	0.8273 (3)	0.7011 (3)	0.0330 (7)
C11	0.8452 (4)	0.8461 (3)	0.8037 (3)	0.0494 (9)
H11	0.7722	0.8396	0.8758	0.059*
C12	0.9972 (5)	0.8745 (4)	0.7994 (4)	0.0647 (11)
H12	1.0250	0.8883	0.8687	0.078*
C13	1.1065 (4)	0.8826 (4)	0.6951 (4)	0.0621 (11)
H13	1.2082	0.9021	0.6930	0.075*
C14	1.0652 (4)	0.8616 (4)	0.5937 (4)	0.0613 (10)
H14	1.1392	0.8654	0.5224	0.074*
C15	0.9136 (4)	0.8347 (4)	0.5970 (3)	0.0522 (9)
H15	0.8868	0.8214	0.5273	0.063*
C16	0.2467 (4)	0.5464 (3)	0.7356 (3)	0.0406 (8)
H16A	0.3313	0.5824	0.7602	0.049*
H16B	0.2128	0.6163	0.6791	0.049*
C17	0.3484 (4)	0.3273 (3)	0.7654 (3)	0.0426 (8)
H17A	0.3823	0.2498	0.7294	0.051*
H17B	0.4345	0.3603	0.7904	0.051*
C18	0.1674 (4)	0.3791 (4)	0.6415 (3)	0.0514 (9)
H18A	0.1325	0.4469	0.5838	0.062*
H18B	0.1985	0.3026	0.6032	0.062*
C19	0.1731 (4)	0.4042 (3)	0.9250 (3)	0.0495 (9)
H19A	0.0898	0.3782	0.9950	0.059*
H19B	0.2571	0.4384	0.9515	0.059*
C20	0.0958 (5)	0.2376 (4)	0.8323 (3)	0.0588 (10)
H20A	0.0125	0.2097	0.9019	0.071*
H20B	0.1279	0.1600	0.7958	0.071*
C21	−0.0058 (4)	0.4567 (4)	0.8024 (4)	0.0579 (10)
H21A	−0.0410	0.5257	0.7458	0.069*
H21B	−0.0906	0.4320	0.8716	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0370 (3)	0.0221 (3)	0.0348 (3)	0.0036 (2)	−0.0136 (3)	−0.0069 (2)
N1	0.0483 (15)	0.0171 (11)	0.0340 (14)	0.0009 (10)	−0.0188 (12)	−0.0038 (10)
N2	0.0338 (13)	0.0198 (11)	0.0273 (13)	0.0031 (10)	−0.0097 (11)	−0.0051 (10)
N3	0.0332 (14)	0.0302 (13)	0.0357 (14)	0.0017 (10)	−0.0075 (11)	−0.0077 (11)
N4	0.0393 (16)	0.0449 (16)	0.0505 (17)	0.0038 (13)	0.0010 (13)	−0.0144 (14)
N5	0.0527 (18)	0.0458 (17)	0.0403 (16)	0.0038 (14)	0.0015 (14)	−0.0038 (13)
N6	0.0420 (17)	0.073 (2)	0.0556 (19)	−0.0165 (16)	−0.0038 (15)	−0.0172 (17)
O1	0.0523 (13)	0.0222 (10)	0.0339 (11)	0.0075 (9)	−0.0195 (10)	−0.0058 (9)
O2	0.0500 (13)	0.0225 (10)	0.0418 (12)	0.0055 (9)	−0.0225 (10)	−0.0029 (9)
O3	0.0410 (12)	0.0306 (11)	0.0442 (13)	0.0004 (9)	−0.0175 (10)	−0.0027 (9)
O4	0.136 (14)	0.121 (13)	0.159 (16)	−0.004 (11)	−0.063 (12)	−0.013 (12)
C1	0.0304 (15)	0.0237 (14)	0.0256 (15)	0.0022 (12)	−0.0046 (12)	−0.0050 (12)
C2	0.0294 (15)	0.0225 (14)	0.0330 (16)	0.0012 (12)	−0.0083 (13)	−0.0033 (12)
C3	0.0365 (16)	0.0217 (14)	0.0328 (16)	0.0011 (12)	−0.0139 (13)	−0.0045 (12)
C4	0.0327 (16)	0.0339 (16)	0.0315 (16)	−0.0006 (13)	−0.0144 (13)	−0.0086 (13)
C5	0.056 (2)	0.0395 (18)	0.0425 (19)	0.0102 (16)	−0.0131 (17)	−0.0118 (15)
C6	0.058 (2)	0.059 (2)	0.056 (2)	0.0220 (19)	−0.0129 (19)	−0.025 (2)
C7	0.044 (2)	0.083 (3)	0.046 (2)	0.001 (2)	−0.0047 (17)	−0.023 (2)
C8	0.051 (2)	0.059 (2)	0.0371 (19)	−0.0106 (18)	−0.0071 (16)	−0.0034 (17)
C9	0.048 (2)	0.0394 (18)	0.0396 (19)	0.0002 (15)	−0.0115 (16)	−0.0062 (15)
C10	0.0380 (17)	0.0217 (14)	0.0408 (18)	−0.0012 (12)	−0.0136 (14)	−0.0036 (13)
C11	0.047 (2)	0.054 (2)	0.050 (2)	−0.0078 (17)	−0.0185 (17)	−0.0077 (17)
C12	0.060 (3)	0.072 (3)	0.073 (3)	−0.011 (2)	−0.036 (2)	−0.011 (2)
C13	0.041 (2)	0.050 (2)	0.099 (3)	−0.0056 (17)	−0.026 (2)	−0.009 (2)
C14	0.042 (2)	0.062 (3)	0.075 (3)	−0.0025 (18)	−0.001 (2)	−0.015 (2)
C15	0.046 (2)	0.060 (2)	0.053 (2)	−0.0035 (17)	−0.0098 (18)	−0.0188 (18)
C16	0.0396 (18)	0.0330 (17)	0.0460 (19)	0.0031 (14)	−0.0021 (15)	−0.0090 (15)
C17	0.0438 (19)	0.0385 (18)	0.0397 (19)	0.0080 (15)	−0.0005 (15)	−0.0049 (15)
C18	0.045 (2)	0.067 (2)	0.044 (2)	−0.0131 (18)	−0.0097 (16)	−0.0150 (18)
C19	0.048 (2)	0.056 (2)	0.0395 (19)	−0.0004 (17)	0.0007 (16)	−0.0105 (17)
C20	0.068 (3)	0.044 (2)	0.055 (2)	−0.0166 (19)	0.011 (2)	−0.0122 (18)
C21	0.0347 (19)	0.072 (3)	0.061 (2)	0.0063 (18)	−0.0026 (17)	−0.008 (2)

Geometric parameters (Å, º)

Co1—O3	2.0849 (19)	C4—C9	1.386 (4)
Co1—O3^i	2.0849 (19)	C5—C6	1.379 (5)
Co1—N2	2.128 (2)	C5—H5	0.9300
Co1—N2^i	2.128 (2)	C6—C7	1.372 (5)
Co1—N3^i	2.359 (2)	C6—H6	0.9300
Co1—N3	2.359 (2)	C7—C8	1.368 (5)
N1—C1	1.341 (3)	C7—H7	0.9300
N1—C3	1.457 (3)	C8—C9	1.383 (5)
N1—H1	0.8600	C8—H8	0.9300
N2—C2	1.351 (3)	C9—H9	0.9300
N2—C1	1.392 (3)	C10—C15	1.374 (4)
N3—C17	1.487 (4)	C10—C11	1.381 (4)
N3—C18	1.491 (4)	C11—C12	1.386 (5)
N3—C16	1.493 (4)	C11—H11	0.9300
N4—C16	1.457 (4)	C12—C13	1.362 (6)
N4—C21	1.458 (4)	C12—H12	0.9300
N4—C19	1.461 (4)	C13—C14	1.366 (5)
N5—C20	1.458 (5)	C13—H13	0.9300
N5—C17	1.461 (4)	C14—C15	1.381 (5)
N5—C19	1.464 (4)	C14—H14	0.9300
N6—C18	1.466 (4)	C15—H15	0.9300
N6—C20	1.471 (5)	C16—H16A	0.9700
N6—C21	1.478 (5)	C16—H16B	0.9700
O1—C1	1.244 (3)	C17—H17A	0.9700
O2—C2	1.230 (3)	C17—H17B	0.9700
O3—H22	0.8500	C18—H18A	0.9700
O3—H23	0.8500	C18—H18B	0.9700
O4—H24	0.8500	C19—H19A	0.9700
O4—H24	0.8500	C19—H19B	0.9700
O4—H25	0.8500	C20—H20A	0.9700
C2—C3	1.563 (4)	C20—H20B	0.9700
C3—C10	1.531 (4)	C21—H21A	0.9700
C3—C4	1.534 (4)	C21—H21B	0.9700
C4—C5	1.386 (4)
O3—Co1—O3^i	180.00 (10)	C8—C7—H7	120.1
O3—Co1—N2	89.95 (8)	C6—C7—H7	120.1
O3^i—Co1—N2	90.05 (8)	C7—C8—C9	120.2 (3)
O3—Co1—N2^i	90.05 (8)	C7—C8—H8	119.9
O3^i—Co1—N2^i	89.95 (8)	C9—C8—H8	119.9
N2—Co1—N2^i	180.0	C8—C9—C4	121.0 (3)
O3—Co1—N3^i	94.17 (8)	C8—C9—H9	119.5
O3^i—Co1—N3^i	85.83 (8)	C4—C9—H9	119.5
N2—Co1—N3^i	89.90 (8)	C15—C10—C11	118.0 (3)
N2^i—Co1—N3^i	90.10 (8)	C15—C10—C3	119.7 (3)
O3—Co1—N3	85.83 (8)	C11—C10—C3	122.2 (3)
O3^i—Co1—N3	94.17 (8)	C10—C11—C12	120.2 (3)
N2—Co1—N3	90.10 (8)	C10—C11—H11	119.9
N2^i—Co1—N3	89.90 (8)	C12—C11—H11	119.9
N3^i—Co1—N3	180.000 (1)	C13—C12—C11	121.0 (4)
C1—N1—C3	112.1 (2)	C13—C12—H12	119.5
C1—N1—H1	124.0	C11—C12—H12	119.5
C3—N1—H1	124.0	C12—C13—C14	119.3 (3)
C2—N2—C1	107.4 (2)	C12—C13—H13	120.3
C2—N2—Co1	125.96 (17)	C14—C13—H13	120.3
C1—N2—Co1	126.68 (17)	C13—C14—C15	120.0 (4)
C17—N3—C18	106.9 (2)	C13—C14—H14	120.0
C17—N3—C16	106.3 (2)	C15—C14—H14	120.0
C18—N3—C16	106.2 (2)	C10—C15—C14	121.5 (3)
C17—N3—Co1	114.39 (17)	C10—C15—H15	119.3
C18—N3—Co1	110.74 (18)	C14—C15—H15	119.3
C16—N3—Co1	111.93 (17)	N4—C16—N3	113.7 (2)
C16—N4—C21	108.3 (3)	N4—C16—H16A	108.8
C16—N4—C19	108.3 (2)	N3—C16—H16A	108.8
C21—N4—C19	108.3 (3)	N4—C16—H16B	108.8
C20—N5—C17	108.2 (3)	N3—C16—H16B	108.8
C20—N5—C19	107.9 (3)	H16A—C16—H16B	107.7
C17—N5—C19	108.6 (3)	N5—C17—N3	113.2 (2)
C18—N6—C20	107.9 (3)	N5—C17—H17A	108.9
C18—N6—C21	108.0 (3)	N3—C17—H17A	108.9
C20—N6—C21	107.9 (3)	N5—C17—H17B	108.9
Co1—O3—H22	106.7	N3—C17—H17B	108.9
Co1—O3—H23	127.8	H17A—C17—H17B	107.7
H22—O3—H23	109.3	N6—C18—N3	113.3 (3)
H24—O4—H25	100.2	N6—C18—H18A	108.9
O1—C1—N1	124.4 (2)	N3—C18—H18A	108.9
O1—C1—N2	124.4 (2)	N6—C18—H18B	108.9
N1—C1—N2	111.2 (2)	N3—C18—H18B	108.9
O2—C2—N2	126.5 (2)	H18A—C18—H18B	107.7
O2—C2—C3	122.9 (2)	N4—C19—N5	112.3 (3)
N2—C2—C3	110.6 (2)	N4—C19—H19A	109.2
N1—C3—C10	112.6 (2)	N5—C19—H19A	109.2
N1—C3—C4	110.8 (2)	N4—C19—H19B	109.2
C10—C3—C4	113.2 (2)	N5—C19—H19B	109.2
N1—C3—C2	98.1 (2)	H19A—C19—H19B	107.9
C10—C3—C2	110.3 (2)	N5—C20—N6	112.6 (3)
C4—C3—C2	110.9 (2)	N5—C20—H20A	109.1
C5—C4—C9	117.7 (3)	N6—C20—H20A	109.1
C5—C4—C3	119.8 (3)	N5—C20—H20B	109.1
C9—C4—C3	122.5 (3)	N6—C20—H20B	109.1
C6—C5—C4	121.1 (3)	H20A—C20—H20B	107.8
C6—C5—H5	119.4	N4—C21—N6	112.0 (3)
C4—C5—H5	119.4	N4—C21—H21A	109.2
C7—C6—C5	120.2 (3)	N6—C21—H21A	109.2
C7—C6—H6	119.9	N4—C21—H21B	109.2
C5—C6—H6	119.9	N6—C21—H21B	109.2
C8—C7—C6	119.7 (3)	H21A—C21—H21B	107.9
O3—Co1—N2—C2	155.4 (2)	C4—C5—C6—C7	0.2 (5)
O3^i—Co1—N2—C2	−24.6 (2)	C5—C6—C7—C8	−0.5 (6)
N3^i—Co1—N2—C2	−110.4 (2)	C6—C7—C8—C9	0.9 (5)
N3—Co1—N2—C2	69.6 (2)	C7—C8—C9—C4	−1.0 (5)
O3—Co1—N2—C1	−23.9 (2)	C5—C4—C9—C8	0.7 (5)
O3^i—Co1—N2—C1	156.1 (2)	C3—C4—C9—C8	178.0 (3)
N3^i—Co1—N2—C1	70.2 (2)	N1—C3—C10—C15	−46.5 (4)
N3—Co1—N2—C1	−109.8 (2)	C4—C3—C10—C15	−173.2 (3)
O3—Co1—N3—C17	174.2 (2)	C2—C3—C10—C15	61.9 (3)
O3^i—Co1—N3—C17	−5.8 (2)	N1—C3—C10—C11	134.7 (3)
N2—Co1—N3—C17	−95.9 (2)	C4—C3—C10—C11	8.1 (4)
N2^i—Co1—N3—C17	84.1 (2)	C2—C3—C10—C11	−116.9 (3)
O3—Co1—N3—C18	53.4 (2)	C15—C10—C11—C12	1.4 (5)
O3^i—Co1—N3—C18	−126.6 (2)	C3—C10—C11—C12	−179.8 (3)
N2—Co1—N3—C18	143.3 (2)	C10—C11—C12—C13	−1.0 (6)
N2^i—Co1—N3—C18	−36.7 (2)	C11—C12—C13—C14	−0.3 (6)
O3—Co1—N3—C16	−64.92 (19)	C12—C13—C14—C15	1.0 (6)
O3^i—Co1—N3—C16	115.08 (19)	C11—C10—C15—C14	−0.7 (5)
N2—Co1—N3—C16	25.02 (19)	C3—C10—C15—C14	−179.5 (3)
N2^i—Co1—N3—C16	−154.98 (19)	C13—C14—C15—C10	−0.5 (6)
C3—N1—C1—O1	173.3 (3)	C21—N4—C16—N3	−58.9 (3)
C3—N1—C1—N2	−7.1 (3)	C19—N4—C16—N3	58.3 (3)
C2—N2—C1—O1	−178.5 (3)	C17—N3—C16—N4	−56.7 (3)
Co1—N2—C1—O1	0.9 (4)	C18—N3—C16—N4	56.8 (3)
C2—N2—C1—N1	1.9 (3)	Co1—N3—C16—N4	177.8 (2)
Co1—N2—C1—N1	−178.66 (18)	C20—N5—C17—N3	58.6 (3)
C1—N2—C2—O2	−177.0 (3)	C19—N5—C17—N3	−58.4 (4)
Co1—N2—C2—O2	3.6 (4)	C18—N3—C17—N5	−56.6 (3)
C1—N2—C2—C3	3.6 (3)	C16—N3—C17—N5	56.5 (3)
Co1—N2—C2—C3	−175.82 (17)	Co1—N3—C17—N5	−179.5 (2)
C1—N1—C3—C10	124.3 (3)	C20—N6—C18—N3	−57.8 (4)
C1—N1—C3—C4	−107.9 (3)	C21—N6—C18—N3	58.6 (4)
C1—N1—C3—C2	8.3 (3)	C17—N3—C18—N6	56.4 (4)
O2—C2—C3—N1	173.5 (3)	C16—N3—C18—N6	−56.7 (4)
N2—C2—C3—N1	−7.1 (3)	Co1—N3—C18—N6	−178.4 (2)
O2—C2—C3—C10	55.7 (4)	C16—N4—C19—N5	−58.1 (3)
N2—C2—C3—C10	−124.9 (3)	C21—N4—C19—N5	59.1 (4)
O2—C2—C3—C4	−70.5 (3)	C20—N5—C19—N4	−58.8 (4)
N2—C2—C3—C4	108.9 (3)	C17—N5—C19—N4	58.3 (4)
N1—C3—C4—C5	−37.7 (3)	C17—N5—C20—N6	−59.1 (4)
C10—C3—C4—C5	89.8 (3)	C19—N5—C20—N6	58.3 (4)
C2—C3—C4—C5	−145.6 (3)	C18—N6—C20—N5	58.7 (4)
N1—C3—C4—C9	144.9 (3)	C21—N6—C20—N5	−57.7 (4)
C10—C3—C4—C9	−87.5 (3)	C16—N4—C21—N6	58.9 (4)
C2—C3—C4—C9	37.1 (4)	C19—N4—C21—N6	−58.3 (4)
C9—C4—C5—C6	−0.3 (5)	C18—N6—C21—N4	−58.9 (4)
C3—C4—C5—C6	−177.7 (3)	C20—N6—C21—N4	57.5 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H22···O1	0.85	2.13	2.714 (3)	125
O4—H24···O3	0.85	2.42	2.879 (12)	114
N1—H1···O1^ii	0.86	2.06	2.892 (3)	163
O4—H25···N6^iii	0.85	2.40	2.940 (14)	122

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