Structure and properties of domperidone and its succinate salt

This paper describes the structure and properties of the drug domperidone and a novel 1:1 domperidone succinate salt. The new salt is characterized by means of thermal, spectroscopic, microscopic and powder diffraction measurements. The crystal structures of the salt and, for the first time, of pure domperidone have been determined by means of single-crystal X-ray diffraction. In both structures, the piperidine ring of domperidone adopts the expected chair conformation, and supramolecular centrosymmetric R₂²(8) motifs are formed by N—H...O hydrogen bonds between chlorine-substituted oxobenzimidazolyl groups. Further N—H...O hydrogen bonds occur between non-substituted oxobenzimidazolyl groups and the resulting C(4) motifs originates hydrogen-bonded chains, extending along the crystallographic b axis. In the salt, a single N—H...O hydrogen bond forms between the protonated nitrogen of the piperidine ring and the carboxylic O atom of the succinate ion. Two alternative and mutually exclusive positions for the nonsubstituted oxobenzimidazolyl group have also been observed; this disorder makes the hydrogen-bonded chains originating from the bicyclic group polar. The dissolution behaviour of the salt in dosage form is compared with two reference commercial products. The salt shows an increased solubility, a characteristic that could be of great advantage from a pharmaceutical view point.

Computing details

For both compounds, data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures

(dom1_p21c)

Crystal data

C22H24ClN5O2	F(000) = 896
Mr = 425.91	Dx = 1.374 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 20.214 (2) Å	θ = 13–19°
b = 6.8155 (9) Å	µ = 0.22 mm^−1
c = 15.8630 (19) Å	T = 293 K
β = 109.604 (9)°	Prism, colourless
V = 2058.7 (4) Å^3	0.6 × 0.45 × 0.3 mm
Z = 4

Data collection

Enraf-Nonius CAD4 diffractometer	2207 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 25.1°, θmin = 1.1°
ω scans	h = −24→22
Absorption correction: ψ scan North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351	k = −8→0
Tmin = 0.943, Tmax = 0.999	l = 0→18
3791 measured reflections	3 standard reflections every 300 min
3639 independent reflections	intensity decay: none

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0461P)^2 + 0.4529P] where P = (Fo^2 + 2Fc^2)/3
3639 reflections	(Δ/σ)max < 0.001
277 parameters	Δρmax = 0.15 e Å^−3
2 restraints	Δρmin = −0.19 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.41904 (14)	0.5576 (4)	0.39099 (16)	0.0409 (6)
C2	0.48363 (13)	0.5677 (4)	0.29945 (15)	0.0361 (6)
C3	0.53706 (14)	0.5675 (4)	0.26375 (17)	0.0424 (6)
H3	0.5840	0.5603	0.2998	0.051*
C4	0.51741 (14)	0.5785 (4)	0.17167 (17)	0.0426 (6)
C5	0.44779 (15)	0.5946 (4)	0.11731 (17)	0.0469 (7)
H5	0.4367	0.6050	0.0557	0.056*
C6	0.39476 (15)	0.5953 (4)	0.15392 (16)	0.0452 (7)
H6	0.3480	0.6074	0.1177	0.054*
C7	0.41285 (13)	0.5775 (4)	0.24605 (16)	0.0382 (6)
C8	0.29721 (13)	0.5637 (4)	0.27956 (17)	0.0451 (7)
H8	0.2866	0.5362	0.3343	0.054*
C9	0.26496 (14)	0.3987 (4)	0.21327 (19)	0.0504 (8)
H9A	0.2825	0.4072	0.1635	0.060*
H9B	0.2795	0.2733	0.2425	0.060*
C10	0.26463 (14)	0.7607 (4)	0.2442 (2)	0.0520 (8)
H10A	0.2807	0.8025	0.1959	0.062*
H10B	0.2797	0.8578	0.2915	0.062*
C11	0.18518 (14)	0.4084 (4)	0.17781 (19)	0.0511 (7)
H11A	0.1671	0.3087	0.1322	0.061*
H11B	0.1671	0.3818	0.2261	0.061*
C12	0.18501 (15)	0.7482 (5)	0.2103 (2)	0.0589 (8)
H12A	0.1687	0.7137	0.2593	0.071*
H12B	0.1653	0.8749	0.1872	0.071*
C13	0.08479 (14)	0.6068 (5)	0.0967 (2)	0.0614 (9)
H13A	0.0627	0.6184	0.1421	0.074*
H13B	0.0691	0.4848	0.0647	0.074*
C14	0.06218 (15)	0.7764 (5)	0.0323 (2)	0.0595 (9)
H14A	0.0822	0.8968	0.0629	0.071*
H14B	0.0114	0.7884	0.0127	0.071*
C15	0.08500 (19)	0.7508 (5)	−0.0487 (2)	0.0704 (10)
H15A	0.1289	0.6787	−0.0310	0.084*
H15B	0.0501	0.6727	−0.0930	0.084*
C16	0.04315 (16)	1.0309 (5)	−0.15589 (19)	0.0562 (9)
C17	0.14088 (16)	1.2172 (5)	−0.11434 (19)	0.0560 (8)
C18	0.1909 (2)	1.3588 (6)	−0.1073 (2)	0.0782 (11)
H18	0.1809	1.4722	−0.1418	0.094*
C19	0.2572 (2)	1.3233 (9)	−0.0456 (3)	0.1013 (16)
H19	0.2926	1.4153	−0.0389	0.122*
C20	0.2716 (2)	1.1577 (10)	0.0049 (3)	0.1051 (19)
H20	0.3166	1.1400	0.0456	0.126*
C21	0.22114 (19)	1.0131 (7)	−0.0020 (2)	0.0832 (13)
H21	0.2313	0.8999	0.0327	0.100*
C22	0.15503 (16)	1.0476 (5)	−0.06350 (18)	0.0588 (9)
Cl1	0.58262 (4)	0.57615 (12)	0.12235 (5)	0.0585 (2)
N1	0.48566 (11)	0.5594 (4)	0.38762 (13)	0.0412 (5)
N2	0.37381 (10)	0.5683 (3)	0.30363 (13)	0.0413 (5)
N3	0.16121 (11)	0.6012 (3)	0.13985 (15)	0.0466 (6)
N4	0.09438 (13)	0.9342 (4)	−0.08959 (15)	0.0588 (7)
N5	0.07140 (13)	1.2038 (4)	−0.16988 (16)	0.0575 (7)
O1	0.40172 (9)	0.5468 (3)	0.45775 (11)	0.0509 (5)
O2	−0.01709 (11)	0.9712 (4)	−0.19349 (14)	0.0721 (7)
H1N	0.5280 (10)	0.532 (5)	0.4355 (15)	0.087*
H5N	0.0499 (15)	1.294 (4)	−0.2169 (16)	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0479 (16)	0.0404 (16)	0.0289 (14)	0.0001 (14)	0.0054 (12)	−0.0029 (13)
C2	0.0439 (15)	0.0300 (14)	0.0278 (13)	0.0023 (13)	0.0033 (11)	0.0007 (12)
C3	0.0439 (15)	0.0355 (15)	0.0400 (15)	−0.0004 (14)	0.0039 (12)	0.0008 (14)
C4	0.0554 (17)	0.0340 (15)	0.0383 (15)	−0.0014 (14)	0.0157 (13)	−0.0014 (13)
C5	0.0616 (19)	0.0462 (18)	0.0271 (13)	−0.0023 (15)	0.0072 (13)	0.0014 (13)
C6	0.0500 (16)	0.0491 (18)	0.0274 (13)	0.0010 (15)	0.0007 (12)	0.0012 (13)
C7	0.0430 (14)	0.0338 (14)	0.0311 (13)	0.0010 (13)	0.0038 (11)	−0.0003 (13)
C8	0.0402 (15)	0.0551 (18)	0.0348 (14)	0.0030 (15)	0.0058 (11)	0.0036 (15)
C9	0.0487 (17)	0.0436 (17)	0.0505 (17)	0.0029 (14)	0.0056 (14)	0.0036 (14)
C10	0.0473 (17)	0.0466 (18)	0.0515 (17)	0.0017 (15)	0.0027 (14)	−0.0091 (15)
C11	0.0465 (17)	0.0478 (18)	0.0523 (17)	−0.0052 (15)	0.0076 (14)	0.0076 (15)
C12	0.0523 (18)	0.058 (2)	0.0580 (19)	0.0098 (16)	0.0081 (15)	−0.0056 (17)
C13	0.0379 (16)	0.070 (2)	0.067 (2)	0.0008 (16)	0.0058 (14)	0.0098 (18)
C14	0.0468 (17)	0.062 (2)	0.0601 (19)	0.0082 (16)	0.0047 (15)	−0.0003 (17)
C15	0.085 (2)	0.056 (2)	0.060 (2)	0.016 (2)	0.0122 (18)	−0.0033 (18)
C16	0.0510 (19)	0.071 (2)	0.0393 (16)	0.0121 (18)	0.0056 (15)	−0.0088 (16)
C17	0.0517 (19)	0.077 (2)	0.0397 (16)	0.0017 (18)	0.0157 (15)	−0.0104 (17)
C18	0.079 (3)	0.105 (3)	0.060 (2)	−0.014 (2)	0.036 (2)	−0.021 (2)
C19	0.069 (3)	0.174 (5)	0.066 (3)	−0.029 (3)	0.030 (2)	−0.045 (3)
C20	0.047 (2)	0.202 (6)	0.055 (2)	0.013 (3)	0.0027 (19)	−0.035 (3)
C21	0.059 (2)	0.131 (4)	0.0461 (19)	0.030 (2)	−0.0007 (17)	−0.008 (2)
C22	0.0558 (19)	0.080 (3)	0.0366 (16)	0.0150 (19)	0.0105 (14)	−0.0055 (17)
Cl1	0.0674 (5)	0.0601 (5)	0.0537 (5)	−0.0005 (4)	0.0282 (4)	−0.0038 (4)
N1	0.0419 (13)	0.0493 (14)	0.0251 (11)	−0.0012 (12)	0.0014 (9)	0.0007 (11)
N2	0.0400 (12)	0.0503 (14)	0.0266 (10)	0.0022 (12)	0.0018 (9)	0.0043 (11)
N3	0.0376 (12)	0.0475 (15)	0.0467 (13)	−0.0002 (11)	0.0035 (10)	0.0018 (12)
N4	0.0584 (16)	0.0629 (18)	0.0466 (14)	0.0106 (15)	0.0061 (12)	−0.0010 (14)
N5	0.0553 (16)	0.069 (2)	0.0428 (14)	0.0093 (15)	0.0093 (12)	0.0063 (14)
O1	0.0523 (11)	0.0696 (14)	0.0276 (9)	0.0015 (11)	0.0091 (8)	−0.0003 (10)
O2	0.0523 (13)	0.0900 (18)	0.0600 (13)	0.0012 (13)	0.0003 (11)	−0.0162 (13)

Geometric parameters (Å, º)

C1—O1	1.224 (3)	C12—H12A	0.9700
C1—N1	1.366 (3)	C12—H12B	0.9700
C1—N2	1.382 (3)	C13—N3	1.465 (3)
C2—C3	1.378 (3)	C13—C14	1.509 (4)
C2—N1	1.386 (3)	C13—H13A	0.9700
C2—C7	1.399 (3)	C13—H13B	0.9700
C3—C4	1.381 (3)	C14—C15	1.514 (4)
C3—H3	0.9300	C14—H14A	0.9700
C4—C5	1.386 (4)	C14—H14B	0.9700
C4—Cl1	1.744 (3)	C15—N4	1.449 (4)
C5—C6	1.380 (4)	C15—H15A	0.9700
C5—H5	0.9300	C15—H15B	0.9700
C6—C7	1.388 (3)	C16—O2	1.232 (3)
C6—H6	0.9300	C16—N5	1.359 (4)
C7—N2	1.394 (3)	C16—N4	1.372 (4)
C8—N2	1.466 (3)	C17—C18	1.375 (5)
C8—C10	1.518 (4)	C17—C22	1.383 (5)
C8—C9	1.528 (4)	C17—N5	1.388 (4)
C8—H8	0.9800	C18—C19	1.390 (5)
C9—C11	1.521 (4)	C18—H18	0.9300
C9—H9A	0.9700	C19—C20	1.359 (7)
C9—H9B	0.9700	C19—H19	0.9300
C10—C12	1.519 (4)	C20—C21	1.396 (6)
C10—H10A	0.9700	C20—H20	0.9300
C10—H10B	0.9700	C21—C22	1.385 (4)
C11—N3	1.459 (3)	C21—H21	0.9300
C11—H11A	0.9700	C22—N4	1.390 (4)
C11—H11B	0.9700	N1—H1N	0.953 (10)
C12—N3	1.457 (4)	N5—H5N	0.951 (10)
O1—C1—N1	127.3 (2)	C14—C13—H13A	109.3
O1—C1—N2	125.8 (3)	N3—C13—H13B	109.3
N1—C1—N2	106.8 (2)	C14—C13—H13B	109.3
C3—C2—N1	130.7 (2)	H13A—C13—H13B	108.0
C3—C2—C7	122.3 (2)	C13—C14—C15	112.2 (3)
N1—C2—C7	106.9 (2)	C13—C14—H14A	109.2
C2—C3—C4	116.6 (2)	C15—C14—H14A	109.2
C2—C3—H3	121.7	C13—C14—H14B	109.2
C4—C3—H3	121.7	C15—C14—H14B	109.2
C3—C4—C5	122.3 (3)	H14A—C14—H14B	107.9
C3—C4—Cl1	118.8 (2)	N4—C15—C14	113.8 (3)
C5—C4—Cl1	118.9 (2)	N4—C15—H15A	108.8
C6—C5—C4	120.6 (2)	C14—C15—H15A	108.8
C6—C5—H5	119.7	N4—C15—H15B	108.8
C4—C5—H5	119.7	C14—C15—H15B	108.8
C5—C6—C7	118.4 (2)	H15A—C15—H15B	107.7
C5—C6—H6	120.8	O2—C16—N5	127.5 (3)
C7—C6—H6	120.8	O2—C16—N4	125.6 (3)
C6—C7—N2	133.4 (2)	N5—C16—N4	106.9 (3)
C6—C7—C2	119.8 (2)	C18—C17—C22	122.4 (3)
N2—C7—C2	106.9 (2)	C18—C17—N5	131.1 (3)
N2—C8—C10	111.5 (2)	C22—C17—N5	106.4 (3)
N2—C8—C9	111.4 (2)	C17—C18—C19	116.4 (4)
C10—C8—C9	111.4 (2)	C17—C18—H18	121.8
N2—C8—H8	107.4	C19—C18—H18	121.8
C10—C8—H8	107.4	C20—C19—C18	121.7 (4)
C9—C8—H8	107.4	C20—C19—H19	119.2
C11—C9—C8	112.2 (2)	C18—C19—H19	119.2
C11—C9—H9A	109.2	C19—C20—C21	122.2 (4)
C8—C9—H9A	109.2	C19—C20—H20	118.9
C11—C9—H9B	109.2	C21—C20—H20	118.9
C8—C9—H9B	109.2	C22—C21—C20	116.3 (4)
H9A—C9—H9B	107.9	C22—C21—H21	121.9
C8—C10—C12	111.0 (2)	C20—C21—H21	121.9
C8—C10—H10A	109.4	C17—C22—C21	121.0 (4)
C12—C10—H10A	109.4	C17—C22—N4	107.6 (3)
C8—C10—H10B	109.4	C21—C22—N4	131.4 (4)
C12—C10—H10B	109.4	C1—N1—C2	110.1 (2)
H10A—C10—H10B	108.0	C1—N1—H1N	127 (2)
N3—C11—C9	110.8 (2)	C2—N1—H1N	122 (2)
N3—C11—H11A	109.5	C1—N2—C7	109.3 (2)
C9—C11—H11A	109.5	C1—N2—C8	123.1 (2)
N3—C11—H11B	109.5	C7—N2—C8	127.66 (19)
C9—C11—H11B	109.5	C12—N3—C11	108.9 (2)
H11A—C11—H11B	108.1	C12—N3—C13	111.4 (2)
N3—C12—C10	110.4 (2)	C11—N3—C13	111.6 (2)
N3—C12—H12A	109.6	C16—N4—C22	108.9 (3)
C10—C12—H12A	109.6	C16—N4—C15	125.4 (3)
N3—C12—H12B	109.6	C22—N4—C15	125.5 (3)
C10—C12—H12B	109.6	C16—N5—C17	110.2 (3)
H12A—C12—H12B	108.1	C16—N5—H5N	125 (2)
N3—C13—C14	111.6 (2)	C17—N5—H5N	124 (2)
N3—C13—H13A	109.3
N1—C2—C3—C4	−179.7 (3)	C3—C2—N1—C1	−178.2 (3)
C7—C2—C3—C4	0.3 (4)	C7—C2—N1—C1	1.8 (3)
C2—C3—C4—C5	1.8 (4)	O1—C1—N2—C7	−179.6 (3)
C2—C3—C4—Cl1	−179.3 (2)	N1—C1—N2—C7	−0.2 (3)
C3—C4—C5—C6	−1.6 (5)	O1—C1—N2—C8	−1.4 (5)
Cl1—C4—C5—C6	179.5 (2)	N1—C1—N2—C8	178.0 (2)
C4—C5—C6—C7	−0.6 (4)	C6—C7—N2—C1	−177.9 (3)
C5—C6—C7—N2	−178.2 (3)	C2—C7—N2—C1	1.3 (3)
C5—C6—C7—C2	2.7 (4)	C6—C7—N2—C8	4.0 (5)
C3—C2—C7—C6	−2.5 (4)	C2—C7—N2—C8	−176.8 (3)
N1—C2—C7—C6	177.4 (3)	C10—C8—N2—C1	110.7 (3)
C3—C2—C7—N2	178.1 (3)	C9—C8—N2—C1	−124.1 (3)
N1—C2—C7—N2	−1.9 (3)	C10—C8—N2—C7	−71.4 (4)
N2—C8—C9—C11	−172.3 (2)	C9—C8—N2—C7	53.7 (4)
C10—C8—C9—C11	−47.1 (3)	C10—C12—N3—C11	65.1 (3)
N2—C8—C10—C12	174.0 (2)	C10—C12—N3—C13	−171.4 (2)
C9—C8—C10—C12	48.8 (3)	C9—C11—N3—C12	−62.7 (3)
C8—C9—C11—N3	54.1 (3)	C9—C11—N3—C13	173.8 (2)
C8—C10—C12—N3	−58.4 (3)	C14—C13—N3—C12	77.0 (3)
N3—C13—C14—C15	68.2 (3)	C14—C13—N3—C11	−161.0 (3)
C13—C14—C15—N4	−153.2 (3)	O2—C16—N4—C22	−179.6 (3)
C22—C17—C18—C19	−0.1 (5)	N5—C16—N4—C22	−0.9 (3)
N5—C17—C18—C19	−177.9 (3)	O2—C16—N4—C15	−4.0 (5)
C17—C18—C19—C20	−0.2 (6)	N5—C16—N4—C15	174.8 (3)
C18—C19—C20—C21	0.3 (6)	C17—C22—N4—C16	0.2 (3)
C19—C20—C21—C22	−0.1 (6)	C21—C22—N4—C16	−177.6 (3)
C18—C17—C22—C21	0.3 (5)	C17—C22—N4—C15	−175.4 (3)
N5—C17—C22—C21	178.6 (3)	C21—C22—N4—C15	6.8 (5)
C18—C17—C22—N4	−177.7 (3)	C14—C15—N4—C16	−89.7 (4)
N5—C17—C22—N4	0.5 (3)	C14—C15—N4—C22	85.3 (4)
C20—C21—C22—C17	−0.2 (5)	O2—C16—N5—C17	180.0 (3)
C20—C21—C22—N4	177.3 (3)	N4—C16—N5—C17	1.2 (3)
O1—C1—N1—C2	178.4 (3)	C18—C17—N5—C16	177.0 (3)
N2—C1—N1—C2	−1.0 (3)	C22—C17—N5—C16	−1.1 (3)

(dom1suc1)

Crystal data

C22H25ClN5O2·C4H5O4	Z = 2
Mr = 544.00	F(000) = 572
Triclinic, P1	Dx = 1.378 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3869 (15) Å	Cell parameters from 25 reflections
b = 8.9838 (15) Å	θ = 6–12°
c = 23.094 (7) Å	µ = 0.20 mm^−1
α = 89.89 (2)°	T = 293 K
β = 82.52 (3)°	PLATY PRISM, colourless
γ = 86.52 (3)°	0.65 × 0.30 × 0.18 mm
V = 1311.4 (5) Å^3

Data collection

Enraf-Nonius CAD4 diffractometer	3233 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
ω scans	h = 0→7
Absorption correction: ψ scan North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351	k = −10→10
Tmin = 0.897, Tmax = 0.966	l = −27→27
5090 measured reflections	3 standard reflections every 300 min
4634 independent reflections	intensity decay: none

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0283P)^2 + 1.3228P] where P = (Fo^2 + 2Fc^2)/3
4634 reflections	(Δ/σ)max < 0.001
439 parameters	Δρmax = 0.28 e Å^−3
71 restraints	Δρmin = −0.26 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Positional disordered affects the terminal 2-oxobenzimidazolyl group. It results disordered over two alternative positions mutually exclusive.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	−0.2954 (3)	0.16562 (16)	0.39061 (7)	0.1145 (6)
C1	0.3180 (6)	0.3837 (4)	0.55504 (15)	0.0516 (9)
C2	0.1093 (6)	0.3075 (4)	0.49069 (15)	0.0529 (9)
C3	0.0091 (7)	0.2840 (4)	0.44244 (17)	0.0671 (11)
H3	0.0555	0.3248	0.4063	0.081*
C4	−0.1620 (7)	0.1980 (5)	0.4501 (2)	0.0724 (12)
C5	−0.2335 (6)	0.1366 (5)	0.5033 (2)	0.0767 (13)
H5	−0.3507	0.0791	0.5066	0.092*
C6	−0.1317 (6)	0.1600 (4)	0.55222 (18)	0.0646 (11)
H6	−0.1784	0.1192	0.5883	0.078*
C7	0.0402 (5)	0.2456 (4)	0.54471 (15)	0.0496 (9)
N1	0.2794 (5)	0.3886 (3)	0.49814 (12)	0.0590 (8)
H1	0.3517	0.4360	0.4708	0.071*
N2	0.1730 (4)	0.2912 (3)	0.58357 (11)	0.0490 (7)
C8	0.1556 (5)	0.2558 (4)	0.64600 (14)	0.0444 (8)
H8	0.0671	0.1705	0.6526	0.053*
C9	0.0482 (5)	0.3841 (4)	0.68378 (15)	0.0470 (8)
H9A	0.1304	0.4713	0.6774	0.056*
H9B	−0.0911	0.4087	0.6727	0.056*
C10	0.3691 (5)	0.2108 (4)	0.66539 (14)	0.0458 (8)
H10A	0.4347	0.1266	0.6421	0.055*
H10B	0.4611	0.2930	0.6590	0.055*
C11	0.0277 (5)	0.3422 (4)	0.74794 (14)	0.0443 (8)
H11A	−0.0355	0.4265	0.7715	0.053*
H11B	−0.0646	0.2603	0.7549	0.053*
C12	0.3439 (5)	0.1695 (3)	0.72897 (14)	0.0447 (8)
H12A	0.2588	0.0836	0.7350	0.054*
H12B	0.4816	0.1428	0.7407	0.054*
C13	0.2197 (6)	0.2638 (4)	0.82949 (15)	0.0525 (9)
H13A	0.1430	0.1743	0.8369	0.063*
H13B	0.1379	0.3453	0.8509	0.063*
C14	0.4319 (6)	0.2416 (4)	0.85197 (16)	0.0582 (10)
H14A	0.5030	0.1494	0.8360	0.070*
H14B	0.5189	0.3227	0.8383	0.070*
C15	0.4110 (7)	0.2361 (5)	0.91789 (18)	0.0727 (12)
H15A	0.5412	0.1976	0.9314	0.087*	0.50
H15B	0.2958	0.1765	0.9339	0.087*	0.50
H15C	0.3000	0.3072	0.9350	0.087*	0.50
H15D	0.5431	0.2573	0.9318	0.087*	0.50
N3	0.2398 (4)	0.2971 (3)	0.76562 (12)	0.0394 (6)
H3N	0.331 (4)	0.379 (2)	0.7606 (13)	0.047*
O1	0.4525 (4)	0.4487 (3)	0.57690 (11)	0.0664 (8)
C23	0.4343 (5)	0.6270 (4)	0.76307 (16)	0.0475 (8)
C24	0.5449 (5)	0.7713 (4)	0.75969 (18)	0.0549 (10)
H24A	0.4935	0.8322	0.7292	0.066*
H24B	0.5064	0.8248	0.7963	0.066*
C25	0.7793 (5)	0.7534 (4)	0.7478 (2)	0.0642 (11)
H25A	0.8199	0.7187	0.7079	0.077*
H25B	0.8302	0.6780	0.7736	0.077*
C26	0.8827 (6)	0.8965 (4)	0.7564 (2)	0.0825 (16)
O3	0.5344 (4)	0.5065 (2)	0.75098 (12)	0.0579 (7)
O4	0.2374 (4)	0.6358 (3)	0.78012 (13)	0.0681 (8)
O5	0.8006 (5)	1.0164 (3)	0.7466 (2)	0.152 (2)
O6	1.0627 (4)	0.8887 (3)	0.77679 (17)	0.0874 (11)
H6O	1.122 (7)	0.788 (2)	0.780 (2)	0.105*
C16A	0.1658 (9)	0.4598 (7)	0.9620 (3)	0.0543 (18)	0.50
C17A	0.3724 (13)	0.6554 (8)	0.9465 (8)	0.049 (3)	0.50
C18A	0.4571 (12)	0.7928 (8)	0.9445 (5)	0.062 (3)	0.50
H18A	0.3779	0.8774	0.9597	0.074*	0.50
C19A	0.6645 (13)	0.8001 (9)	0.9192 (5)	0.076 (3)	0.50
H19A	0.7245	0.8920	0.9162	0.091*	0.50
C20A	0.7844 (13)	0.6742 (11)	0.8983 (6)	0.082 (4)	0.50
H20A	0.9252	0.6822	0.8829	0.098*	0.50
C21A	0.6983 (9)	0.5351 (9)	0.8999 (3)	0.070 (2)	0.50
H21A	0.7773	0.4507	0.8844	0.084*	0.50
C22A	0.4919 (8)	0.5276 (6)	0.9252 (3)	0.0527 (18)	0.50
N4A	0.3613 (8)	0.4097 (5)	0.9339 (2)	0.0516 (14)	0.50
N5A	0.1768 (8)	0.6102 (6)	0.9697 (2)	0.0543 (15)	0.50
H5A	0.0755	0.6685	0.9866	0.065*	0.50
O2A	0.0127 (8)	0.3827 (6)	0.9759 (2)	0.0732 (16)	0.50
C16B	0.1493 (9)	0.0310 (7)	0.9565 (3)	0.0542 (18)	0.50
C17B	0.3621 (10)	−0.1802 (7)	0.9444 (5)	0.048 (2)	0.50
C18B	0.4488 (14)	−0.3243 (8)	0.9431 (9)	0.065 (3)	0.50
H18B	0.3674	−0.4036	0.9556	0.078*	0.50
C19B	0.6606 (13)	−0.3466 (9)	0.9227 (4)	0.081 (3)	0.50
H19B	0.7234	−0.4429	0.9214	0.097*	0.50
C20B	0.7823 (13)	−0.2297 (10)	0.9039 (7)	0.086 (4)	0.50
H20B	0.9250	−0.2486	0.8903	0.103*	0.50
C21B	0.6949 (9)	−0.0838 (8)	0.9051 (3)	0.069 (2)	0.50
H21B	0.7767	−0.0048	0.8927	0.083*	0.50
C22B	0.4831 (8)	−0.0609 (6)	0.9253 (3)	0.0511 (17)	0.50
N4B	0.3495 (8)	0.0670 (5)	0.9326 (2)	0.0516 (14)	0.50
N5B	0.1613 (8)	−0.1201 (6)	0.9638 (2)	0.0570 (16)	0.50
H5B	0.0577	−0.1710	0.9785	0.068*	0.50
O2B	−0.0057 (9)	0.1194 (6)	0.9679 (2)	0.0724 (16)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1342 (13)	0.1039 (10)	0.1223 (12)	−0.0136 (9)	−0.0776 (10)	−0.0274 (9)
C1	0.056 (2)	0.044 (2)	0.055 (2)	−0.0097 (17)	−0.0077 (18)	0.0033 (17)
C2	0.058 (2)	0.042 (2)	0.061 (2)	−0.0051 (17)	−0.0178 (19)	−0.0040 (17)
C3	0.082 (3)	0.054 (2)	0.068 (3)	−0.003 (2)	−0.021 (2)	−0.008 (2)
C4	0.074 (3)	0.063 (3)	0.086 (3)	0.001 (2)	−0.036 (3)	−0.019 (2)
C5	0.056 (3)	0.077 (3)	0.102 (4)	−0.018 (2)	−0.023 (3)	−0.017 (3)
C6	0.049 (2)	0.071 (3)	0.075 (3)	−0.011 (2)	−0.007 (2)	−0.002 (2)
C7	0.0427 (19)	0.046 (2)	0.061 (2)	−0.0040 (16)	−0.0085 (17)	−0.0059 (17)
N1	0.071 (2)	0.0589 (19)	0.0500 (19)	−0.0190 (17)	−0.0124 (16)	0.0077 (15)
N2	0.0454 (16)	0.0514 (17)	0.0508 (18)	−0.0131 (14)	−0.0042 (14)	0.0026 (14)
C8	0.0429 (19)	0.0392 (18)	0.051 (2)	−0.0116 (15)	−0.0022 (15)	0.0052 (15)
C9	0.0412 (19)	0.0398 (18)	0.059 (2)	0.0006 (15)	−0.0060 (16)	0.0056 (16)
C10	0.0403 (18)	0.0413 (18)	0.053 (2)	−0.0010 (15)	0.0030 (15)	−0.0012 (16)
C11	0.0344 (17)	0.0368 (18)	0.060 (2)	−0.0007 (14)	0.0004 (15)	0.0003 (15)
C12	0.0403 (18)	0.0291 (16)	0.062 (2)	0.0021 (14)	0.0000 (16)	0.0026 (15)
C13	0.053 (2)	0.051 (2)	0.050 (2)	−0.0008 (17)	0.0031 (17)	0.0071 (17)
C14	0.061 (2)	0.056 (2)	0.057 (2)	0.0016 (19)	−0.0105 (19)	0.0053 (18)
C15	0.073 (3)	0.084 (3)	0.062 (3)	0.008 (2)	−0.018 (2)	−0.006 (2)
N3	0.0346 (14)	0.0313 (14)	0.0511 (16)	−0.0053 (11)	0.0004 (12)	0.0022 (12)
O1	0.0800 (19)	0.0680 (17)	0.0589 (16)	−0.0410 (15)	−0.0208 (14)	0.0137 (13)
C23	0.0384 (19)	0.0348 (18)	0.073 (2)	−0.0085 (15)	−0.0172 (17)	0.0089 (17)
C24	0.0361 (19)	0.0346 (18)	0.095 (3)	−0.0053 (15)	−0.0099 (18)	0.0002 (18)
C25	0.0373 (19)	0.0324 (18)	0.120 (4)	−0.0031 (15)	0.001 (2)	0.003 (2)
C26	0.029 (2)	0.033 (2)	0.181 (5)	−0.0028 (16)	0.002 (2)	0.005 (2)
O3	0.0444 (14)	0.0319 (13)	0.097 (2)	−0.0057 (11)	−0.0085 (13)	0.0030 (12)
O4	0.0332 (14)	0.0455 (14)	0.126 (2)	−0.0095 (11)	−0.0079 (14)	0.0049 (15)
O5	0.0448 (18)	0.0368 (17)	0.377 (7)	−0.0056 (14)	−0.039 (3)	0.035 (3)
O6	0.0400 (16)	0.0422 (15)	0.179 (3)	−0.0120 (12)	−0.0077 (18)	−0.0013 (19)
C16A	0.049 (4)	0.066 (5)	0.046 (4)	0.009 (4)	−0.007 (3)	0.008 (4)
C17A	0.045 (6)	0.052 (5)	0.049 (5)	0.006 (4)	−0.008 (6)	0.009 (4)
C18A	0.066 (8)	0.068 (7)	0.054 (6)	−0.005 (6)	−0.017 (6)	0.005 (5)
C19A	0.079 (9)	0.084 (8)	0.069 (7)	−0.022 (6)	−0.024 (7)	0.019 (6)
C20A	0.055 (7)	0.129 (12)	0.065 (7)	−0.028 (7)	−0.007 (5)	0.009 (8)
C21A	0.046 (5)	0.106 (7)	0.057 (5)	0.005 (5)	−0.004 (4)	−0.009 (5)
C22A	0.047 (4)	0.068 (5)	0.042 (4)	0.007 (4)	−0.007 (3)	0.000 (3)
N4A	0.052 (4)	0.056 (4)	0.046 (3)	0.002 (3)	−0.005 (3)	−0.006 (3)
N5A	0.047 (4)	0.059 (4)	0.054 (4)	0.010 (3)	−0.001 (3)	0.004 (3)
O2A	0.055 (3)	0.080 (4)	0.081 (4)	−0.006 (3)	0.004 (3)	0.020 (3)
C16B	0.052 (4)	0.060 (5)	0.049 (4)	−0.001 (4)	−0.001 (3)	−0.003 (4)
C17B	0.046 (6)	0.060 (5)	0.040 (4)	0.002 (4)	−0.010 (5)	0.003 (4)
C18B	0.064 (9)	0.060 (7)	0.072 (7)	0.002 (6)	−0.014 (8)	0.001 (6)
C19B	0.075 (8)	0.085 (8)	0.083 (8)	0.026 (6)	−0.024 (6)	0.003 (6)
C20B	0.065 (8)	0.110 (11)	0.081 (9)	0.025 (8)	−0.018 (7)	0.007 (9)
C21B	0.053 (5)	0.094 (7)	0.062 (5)	−0.008 (5)	−0.013 (4)	0.015 (5)
C22B	0.051 (4)	0.059 (5)	0.045 (4)	−0.002 (4)	−0.011 (3)	0.006 (3)
N4B	0.056 (4)	0.050 (3)	0.048 (3)	−0.002 (3)	−0.003 (3)	0.004 (3)
N5B	0.056 (4)	0.059 (4)	0.055 (4)	−0.006 (3)	0.000 (3)	0.003 (3)
O2B	0.066 (4)	0.068 (4)	0.078 (4)	0.014 (3)	0.003 (3)	−0.013 (3)

Geometric parameters (Å, º)

Cl1—C4	1.742 (4)	C23—C24	1.511 (4)
C1—O1	1.228 (4)	C24—C25	1.486 (4)
C1—N1	1.368 (4)	C24—H24A	0.9700
C1—N2	1.384 (4)	C24—H24B	0.9700
C2—N1	1.374 (4)	C25—C26	1.506 (5)
C2—C3	1.378 (4)	C25—H25A	0.9700
C2—C7	1.394 (5)	C25—H25B	0.9700
C3—C4	1.369 (5)	C26—O5	1.202 (4)
C3—H3	0.9300	C26—O6	1.297 (5)
C4—C5	1.380 (5)	O6—H6O	0.963 (10)
C5—C6	1.397 (5)	C16A—O2A	1.240 (7)
C5—H5	0.9300	C16A—N5A	1.371 (6)
C6—C7	1.371 (4)	C16A—N4A	1.381 (6)
C6—H6	0.9300	C17A—C18A	1.376 (7)
C7—N2	1.391 (4)	C17A—N5A	1.378 (7)
N1—H1	0.8600	C17A—C22A	1.393 (7)
N2—C8	1.467 (4)	C18A—C19A	1.382 (8)
C8—C9	1.520 (4)	C18A—H18A	0.9300
C8—C10	1.521 (4)	C19A—C20A	1.378 (8)
C8—H8	0.9800	C19A—H19A	0.9300
C9—C11	1.519 (4)	C20A—C21A	1.394 (8)
C9—H9A	0.9700	C20A—H20A	0.9300
C9—H9B	0.9700	C21A—C22A	1.376 (6)
C10—C12	1.504 (4)	C21A—H21A	0.9300
C10—H10A	0.9700	C22A—N4A	1.385 (6)
C10—H10B	0.9700	N5A—H5A	0.8600
C11—N3	1.497 (4)	O2A—N5A^i	1.627 (7)
C11—H11A	0.9700	C16B—O2B	1.232 (7)
C11—H11B	0.9700	C16B—N5B	1.367 (6)
C12—N3	1.496 (4)	C16B—N4B	1.382 (6)
C12—H12A	0.9700	C17B—C18B	1.376 (7)
C12—H12B	0.9700	C17B—N5B	1.380 (6)
C13—N3	1.495 (4)	C17B—C22B	1.396 (7)
C13—C14	1.515 (5)	C18B—C19B	1.377 (8)
C13—H13A	0.9700	C18B—H18B	0.9300
C13—H13B	0.9700	C19B—C20B	1.380 (8)
C14—C15	1.512 (5)	C19B—H19B	0.9300
C14—H14A	0.9700	C20B—C21B	1.392 (8)
C14—H14B	0.9700	C20B—H20B	0.9300
C15—N4A	1.607 (6)	C21B—C22B	1.376 (6)
C15—H15A	0.9700	C21B—H21B	0.9300
C15—H15B	0.9700	C22B—N4B	1.386 (6)
N3—H3N	0.966 (10)	N5B—H5B	0.8600
C23—O3	1.237 (4)	O2B—N5B^ii	1.750 (7)
C23—O4	1.266 (4)
O1—C1—N1	127.4 (3)	C12—N3—C11	110.8 (3)
O1—C1—N2	126.5 (3)	C13—N3—H3N	104.7 (18)
N1—C1—N2	106.1 (3)	C12—N3—H3N	108.1 (19)
N1—C2—C3	131.6 (3)	C11—N3—H3N	110.2 (19)
N1—C2—C7	106.9 (3)	O3—C23—O4	122.3 (3)
C3—C2—C7	121.5 (3)	O3—C23—C24	120.9 (3)
C4—C3—C2	116.9 (4)	O4—C23—C24	116.8 (3)
C4—C3—H3	121.5	C25—C24—C23	114.7 (3)
C2—C3—H3	121.5	C25—C24—H24A	108.6
C3—C4—C5	122.4 (4)	C23—C24—H24A	108.6
C3—C4—Cl1	118.8 (4)	C25—C24—H24B	108.6
C5—C4—Cl1	118.7 (3)	C23—C24—H24B	108.6
C4—C5—C6	120.7 (4)	H24A—C24—H24B	107.6
C4—C5—H5	119.7	C24—C25—C26	112.4 (3)
C6—C5—H5	119.7	C24—C25—H25A	109.1
C7—C6—C5	117.1 (4)	C26—C25—H25A	109.1
C7—C6—H6	121.5	C24—C25—H25B	109.1
C5—C6—H6	121.5	C26—C25—H25B	109.1
C6—C7—N2	131.7 (3)	H25A—C25—H25B	107.9
C6—C7—C2	121.4 (3)	O5—C26—O6	119.7 (4)
N2—C7—C2	106.9 (3)	O5—C26—C25	122.2 (4)
C1—N1—C2	110.7 (3)	O6—C26—C25	118.1 (3)
C1—N1—H1	124.7	C26—O6—H6O	114 (3)
C2—N1—H1	124.7	O2A—C16A—N5A	128.2 (6)
C1—N2—C7	109.3 (3)	O2A—C16A—N4A	126.1 (6)
C1—N2—C8	124.6 (3)	N5A—C16A—N4A	105.7 (4)
C7—N2—C8	125.9 (3)	C18A—C17A—N5A	131.7 (6)
N2—C8—C9	112.0 (3)	C18A—C17A—C22A	121.6 (6)
N2—C8—C10	112.3 (3)	N5A—C17A—C22A	106.6 (5)
C9—C8—C10	109.8 (3)	C17A—C18A—C19A	117.4 (6)
N2—C8—H8	107.5	C17A—C18A—H18A	121.3
C9—C8—H8	107.5	C19A—C18A—H18A	121.3
C10—C8—H8	107.5	C20A—C19A—C18A	121.5 (6)
C11—C9—C8	110.6 (3)	C20A—C19A—H19A	119.3
C11—C9—H9A	109.5	C18A—C19A—H19A	119.3
C8—C9—H9A	109.5	C19A—C20A—C21A	121.1 (6)
C11—C9—H9B	109.5	C19A—C20A—H20A	119.4
C8—C9—H9B	109.5	C21A—C20A—H20A	119.4
H9A—C9—H9B	108.1	C22A—C21A—C20A	117.4 (6)
C12—C10—C8	110.7 (3)	C22A—C21A—H21A	121.3
C12—C10—H10A	109.5	C20A—C21A—H21A	121.3
C8—C10—H10A	109.5	C21A—C22A—N4A	132.1 (5)
C12—C10—H10B	109.5	C21A—C22A—C17A	120.9 (5)
C8—C10—H10B	109.5	N4A—C22A—C17A	107.0 (4)
H10A—C10—H10B	108.1	C16A—N4A—C22A	109.8 (4)
N3—C11—C9	110.7 (3)	C16A—N4A—C15	120.5 (4)
N3—C11—H11A	109.5	C22A—N4A—C15	129.6 (4)
C9—C11—H11A	109.5	C16A—N5A—C17A	110.7 (5)
N3—C11—H11B	109.5	C16A—N5A—H5A	124.6
C9—C11—H11B	109.5	C17A—N5A—H5A	124.6
H11A—C11—H11B	108.1	C16A—O2A—N5A^i	133.0 (6)
N3—C12—C10	110.4 (2)	O2B—C16B—N5B	128.3 (6)
N3—C12—H12A	109.6	O2B—C16B—N4B	125.9 (6)
C10—C12—H12A	109.6	N5B—C16B—N4B	105.8 (4)
N3—C12—H12B	109.6	C18B—C17B—N5B	131.8 (6)
C10—C12—H12B	109.6	C18B—C17B—C22B	121.6 (6)
H12A—C12—H12B	108.1	N5B—C17B—C22B	106.6 (4)
N3—C13—C14	112.8 (3)	C17B—C18B—C19B	117.4 (6)
N3—C13—H13A	109.0	C17B—C18B—H18B	121.3
C14—C13—H13A	109.0	C19B—C18B—H18B	121.3
N3—C13—H13B	109.0	C18B—C19B—C20B	121.7 (6)
C14—C13—H13B	109.0	C18B—C19B—H19B	119.2
H13A—C13—H13B	107.8	C20B—C19B—H19B	119.2
C15—C14—C13	112.5 (3)	C19B—C20B—C21B	121.0 (6)
C15—C14—H14A	109.1	C19B—C20B—H20B	119.5
C13—C14—H14A	109.1	C21B—C20B—H20B	119.5
C15—C14—H14B	109.1	C22B—C21B—C20B	117.6 (6)
C13—C14—H14B	109.1	C22B—C21B—H21B	121.2
H14A—C14—H14B	107.8	C20B—C21B—H21B	121.2
C14—C15—N4A	100.7 (3)	C21B—C22B—N4B	132.3 (5)
C14—C15—H15A	111.6	C21B—C22B—C17B	120.8 (5)
N4A—C15—H15A	111.6	N4B—C22B—C17B	106.9 (4)
C14—C15—H15B	111.6	C16B—N4B—C22B	109.9 (4)
N4A—C15—H15B	111.6	C16B—N5B—C17B	110.9 (5)
H15A—C15—H15B	109.4	C16B—N5B—H5B	124.6
C13—N3—C12	112.5 (2)	C17B—N5B—H5B	124.6
C13—N3—C11	110.4 (2)	C16B—O2B—N5B^ii	121.4 (5)
N1—C2—C3—C4	−178.7 (4)	N5A—C17A—C18A—C19A	177.9 (15)
C7—C2—C3—C4	0.4 (6)	C22A—C17A—C18A—C19A	2 (2)
C2—C3—C4—C5	0.1 (6)	C17A—C18A—C19A—C20A	−2.0 (19)
C2—C3—C4—Cl1	179.7 (3)	C18A—C19A—C20A—C21A	2.5 (19)
C3—C4—C5—C6	−0.3 (7)	C19A—C20A—C21A—C22A	−2.5 (16)
Cl1—C4—C5—C6	−179.8 (3)	C20A—C21A—C22A—N4A	−179.8 (9)
C4—C5—C6—C7	0.0 (6)	C20A—C21A—C22A—C17A	2.1 (15)
C5—C6—C7—N2	179.1 (4)	C18A—C17A—C22A—C21A	−2 (2)
C5—C6—C7—C2	0.5 (6)	N5A—C17A—C22A—C21A	−178.9 (9)
N1—C2—C7—C6	178.6 (3)	C18A—C17A—C22A—N4A	179.7 (13)
C3—C2—C7—C6	−0.7 (6)	N5A—C17A—C22A—N4A	2.6 (14)
N1—C2—C7—N2	−0.3 (4)	O2A—C16A—N4A—C22A	179.4 (7)
C3—C2—C7—N2	−179.6 (3)	N5A—C16A—N4A—C22A	0.9 (8)
O1—C1—N1—C2	−176.8 (4)	O2A—C16A—N4A—C15	−2.3 (10)
N2—C1—N1—C2	2.6 (4)	N5A—C16A—N4A—C15	179.3 (5)
C3—C2—N1—C1	177.7 (4)	C21A—C22A—N4A—C16A	179.5 (8)
C7—C2—N1—C1	−1.5 (4)	C17A—C22A—N4A—C16A	−2.2 (11)
O1—C1—N2—C7	176.7 (4)	C21A—C22A—N4A—C15	1.3 (12)
N1—C1—N2—C7	−2.8 (4)	C17A—C22A—N4A—C15	179.6 (9)
O1—C1—N2—C8	0.4 (6)	C14—C15—N4A—C16A	112.6 (6)
N1—C1—N2—C8	−179.1 (3)	C14—C15—N4A—C22A	−69.4 (7)
C6—C7—N2—C1	−176.9 (4)	O2A—C16A—N5A—C17A	−177.7 (11)
C2—C7—N2—C1	1.9 (4)	N4A—C16A—N5A—C17A	0.8 (11)
C6—C7—N2—C8	−0.6 (6)	C18A—C17A—N5A—C16A	−178.8 (16)
C2—C7—N2—C8	178.2 (3)	C22A—C17A—N5A—C16A	−2.1 (15)
C1—N2—C8—C9	75.9 (4)	N5A—C16A—O2A—N5A^i	−34.9 (13)
C7—N2—C8—C9	−99.8 (4)	N4A—C16A—O2A—N5A^i	147.0 (6)
C1—N2—C8—C10	−48.1 (4)	N5B—C17B—C18B—C19B	−177.4 (12)
C7—N2—C8—C10	136.2 (3)	C22B—C17B—C18B—C19B	0 (2)
N2—C8—C9—C11	178.5 (3)	C17B—C18B—C19B—C20B	0 (2)
C10—C8—C9—C11	−56.0 (3)	C18B—C19B—C20B—C21B	0 (2)
N2—C8—C10—C12	−177.7 (3)	C19B—C20B—C21B—C22B	−0.4 (19)
C9—C8—C10—C12	57.0 (3)	C20B—C21B—C22B—N4B	179.5 (10)
C8—C9—C11—N3	56.7 (3)	C20B—C21B—C22B—C17B	0.6 (14)
C8—C10—C12—N3	−58.3 (3)	C18B—C17B—C22B—C21B	−0.7 (17)
N3—C13—C14—C15	169.5 (3)	N5B—C17B—C22B—C21B	177.6 (7)
C13—C14—C15—N4A	−75.8 (4)	C18B—C17B—C22B—N4B	−179.8 (13)
C14—C13—N3—C12	64.9 (4)	N5B—C17B—C22B—N4B	−1.5 (10)
C14—C13—N3—C11	−170.8 (3)	O2B—C16B—N4B—C22B	−179.5 (7)
C10—C12—N3—C13	−177.5 (3)	N5B—C16B—N4B—C22B	−0.1 (8)
C10—C12—N3—C11	58.5 (3)	C21B—C22B—N4B—C16B	−178.0 (8)
C9—C11—N3—C13	177.0 (3)	C17B—C22B—N4B—C16B	1.0 (9)
C9—C11—N3—C12	−57.7 (3)	O2B—C16B—N5B—C17B	178.5 (8)
O3—C23—C24—C25	−6.7 (5)	N4B—C16B—N5B—C17B	−0.9 (9)
O4—C23—C24—C25	171.6 (4)	C18B—C17B—N5B—C16B	179.6 (15)
C23—C24—C25—C26	−168.9 (4)	C22B—C17B—N5B—C16B	1.5 (10)
C24—C25—C26—O5	−32.4 (7)	N5B—C16B—O2B—N5B^ii	50.2 (11)
C24—C25—C26—O6	145.3 (4)	N4B—C16B—O2B—N5B^ii	−130.4 (7)

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