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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519213016989/zb5028sup1.cif
Contains datablocks dom1_p21c, dom1suc1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213016989/zb5028dom1_p21csup2.hkl
Contains datablock dom1_p21c

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213016989/zb5028dom1suc1sup3.hkl
Contains datablock dom1suc1

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052519213016989/zb5028sup4.pdf
Extra figures

CCDC references: 903316; 903317

Computing details top

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 top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
(dom1_p21c) top
Crystal data top
C22H24ClN5O2F(000) = 896
Mr = 425.91Dx = 1.374 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 20.214 (2) Åθ = 13–19°
b = 6.8155 (9) ŵ = 0.22 mm1
c = 15.8630 (19) ÅT = 293 K
β = 109.604 (9)°Prism, colourless
V = 2058.7 (4) Å30.6 × 0.45 × 0.3 mm
Z = 4
Data collection top
Enraf-Nonius CAD4
diffractometer
2207 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 25.1°, θmin = 1.1°
ω scansh = 2422
Absorption correction: ψ scan
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
k = 80
Tmin = 0.943, Tmax = 0.999l = 018
3791 measured reflections3 standard reflections every 300 min
3639 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0461P)2 + 0.4529P]
where P = (Fo2 + 2Fc2)/3
3639 reflections(Δ/σ)max < 0.001
277 parametersΔρmax = 0.15 e Å3
2 restraintsΔρmin = 0.19 e Å3
Crystal data top
C22H24ClN5O2V = 2058.7 (4) Å3
Mr = 425.91Z = 4
Monoclinic, P21/cMo Kα radiation
a = 20.214 (2) ŵ = 0.22 mm1
b = 6.8155 (9) ÅT = 293 K
c = 15.8630 (19) Å0.6 × 0.45 × 0.3 mm
β = 109.604 (9)°
Data collection top
Enraf-Nonius CAD4
diffractometer
2207 reflections with I > 2σ(I)
Absorption correction: ψ scan
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Rint = 0.016
Tmin = 0.943, Tmax = 0.9993 standard reflections every 300 min
3791 measured reflections intensity decay: none
3639 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0482 restraints
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.15 e Å3
3639 reflectionsΔρmin = 0.19 e Å3
277 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.41904 (14)0.5576 (4)0.39099 (16)0.0409 (6)
C20.48363 (13)0.5677 (4)0.29945 (15)0.0361 (6)
C30.53706 (14)0.5675 (4)0.26375 (17)0.0424 (6)
H30.58400.56030.29980.051*
C40.51741 (14)0.5785 (4)0.17167 (17)0.0426 (6)
C50.44779 (15)0.5946 (4)0.11731 (17)0.0469 (7)
H50.43670.60500.05570.056*
C60.39476 (15)0.5953 (4)0.15392 (16)0.0452 (7)
H60.34800.60740.11770.054*
C70.41285 (13)0.5775 (4)0.24605 (16)0.0382 (6)
C80.29721 (13)0.5637 (4)0.27956 (17)0.0451 (7)
H80.28660.53620.33430.054*
C90.26496 (14)0.3987 (4)0.21327 (19)0.0504 (8)
H9A0.28250.40720.16350.060*
H9B0.27950.27330.24250.060*
C100.26463 (14)0.7607 (4)0.2442 (2)0.0520 (8)
H10A0.28070.80250.19590.062*
H10B0.27970.85780.29150.062*
C110.18518 (14)0.4084 (4)0.17781 (19)0.0511 (7)
H11A0.16710.30870.13220.061*
H11B0.16710.38180.22610.061*
C120.18501 (15)0.7482 (5)0.2103 (2)0.0589 (8)
H12A0.16870.71370.25930.071*
H12B0.16530.87490.18720.071*
C130.08479 (14)0.6068 (5)0.0967 (2)0.0614 (9)
H13A0.06270.61840.14210.074*
H13B0.06910.48480.06470.074*
C140.06218 (15)0.7764 (5)0.0323 (2)0.0595 (9)
H14A0.08220.89680.06290.071*
H14B0.01140.78840.01270.071*
C150.08500 (19)0.7508 (5)0.0487 (2)0.0704 (10)
H15A0.12890.67870.03100.084*
H15B0.05010.67270.09300.084*
C160.04315 (16)1.0309 (5)0.15589 (19)0.0562 (9)
C170.14088 (16)1.2172 (5)0.11434 (19)0.0560 (8)
C180.1909 (2)1.3588 (6)0.1073 (2)0.0782 (11)
H180.18091.47220.14180.094*
C190.2572 (2)1.3233 (9)0.0456 (3)0.1013 (16)
H190.29261.41530.03890.122*
C200.2716 (2)1.1577 (10)0.0049 (3)0.1051 (19)
H200.31661.14000.04560.126*
C210.22114 (19)1.0131 (7)0.0020 (2)0.0832 (13)
H210.23130.89990.03270.100*
C220.15503 (16)1.0476 (5)0.06350 (18)0.0588 (9)
Cl10.58262 (4)0.57615 (12)0.12235 (5)0.0585 (2)
N10.48566 (11)0.5594 (4)0.38762 (13)0.0412 (5)
N20.37381 (10)0.5683 (3)0.30363 (13)0.0413 (5)
N30.16121 (11)0.6012 (3)0.13985 (15)0.0466 (6)
N40.09438 (13)0.9342 (4)0.08959 (15)0.0588 (7)
N50.07140 (13)1.2038 (4)0.16988 (16)0.0575 (7)
O10.40172 (9)0.5468 (3)0.45775 (11)0.0509 (5)
O20.01709 (11)0.9712 (4)0.19349 (14)0.0721 (7)
H1N0.5280 (10)0.532 (5)0.4355 (15)0.087*
H5N0.0499 (15)1.294 (4)0.2169 (16)0.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0479 (16)0.0404 (16)0.0289 (14)0.0001 (14)0.0054 (12)0.0029 (13)
C20.0439 (15)0.0300 (14)0.0278 (13)0.0023 (13)0.0033 (11)0.0007 (12)
C30.0439 (15)0.0355 (15)0.0400 (15)0.0004 (14)0.0039 (12)0.0008 (14)
C40.0554 (17)0.0340 (15)0.0383 (15)0.0014 (14)0.0157 (13)0.0014 (13)
C50.0616 (19)0.0462 (18)0.0271 (13)0.0023 (15)0.0072 (13)0.0014 (13)
C60.0500 (16)0.0491 (18)0.0274 (13)0.0010 (15)0.0007 (12)0.0012 (13)
C70.0430 (14)0.0338 (14)0.0311 (13)0.0010 (13)0.0038 (11)0.0003 (13)
C80.0402 (15)0.0551 (18)0.0348 (14)0.0030 (15)0.0058 (11)0.0036 (15)
C90.0487 (17)0.0436 (17)0.0505 (17)0.0029 (14)0.0056 (14)0.0036 (14)
C100.0473 (17)0.0466 (18)0.0515 (17)0.0017 (15)0.0027 (14)0.0091 (15)
C110.0465 (17)0.0478 (18)0.0523 (17)0.0052 (15)0.0076 (14)0.0076 (15)
C120.0523 (18)0.058 (2)0.0580 (19)0.0098 (16)0.0081 (15)0.0056 (17)
C130.0379 (16)0.070 (2)0.067 (2)0.0008 (16)0.0058 (14)0.0098 (18)
C140.0468 (17)0.062 (2)0.0601 (19)0.0082 (16)0.0047 (15)0.0003 (17)
C150.085 (2)0.056 (2)0.060 (2)0.016 (2)0.0122 (18)0.0033 (18)
C160.0510 (19)0.071 (2)0.0393 (16)0.0121 (18)0.0056 (15)0.0088 (16)
C170.0517 (19)0.077 (2)0.0397 (16)0.0017 (18)0.0157 (15)0.0104 (17)
C180.079 (3)0.105 (3)0.060 (2)0.014 (2)0.036 (2)0.021 (2)
C190.069 (3)0.174 (5)0.066 (3)0.029 (3)0.030 (2)0.045 (3)
C200.047 (2)0.202 (6)0.055 (2)0.013 (3)0.0027 (19)0.035 (3)
C210.059 (2)0.131 (4)0.0461 (19)0.030 (2)0.0007 (17)0.008 (2)
C220.0558 (19)0.080 (3)0.0366 (16)0.0150 (19)0.0105 (14)0.0055 (17)
Cl10.0674 (5)0.0601 (5)0.0537 (5)0.0005 (4)0.0282 (4)0.0038 (4)
N10.0419 (13)0.0493 (14)0.0251 (11)0.0012 (12)0.0014 (9)0.0007 (11)
N20.0400 (12)0.0503 (14)0.0266 (10)0.0022 (12)0.0018 (9)0.0043 (11)
N30.0376 (12)0.0475 (15)0.0467 (13)0.0002 (11)0.0035 (10)0.0018 (12)
N40.0584 (16)0.0629 (18)0.0466 (14)0.0106 (15)0.0061 (12)0.0010 (14)
N50.0553 (16)0.069 (2)0.0428 (14)0.0093 (15)0.0093 (12)0.0063 (14)
O10.0523 (11)0.0696 (14)0.0276 (9)0.0015 (11)0.0091 (8)0.0003 (10)
O20.0523 (13)0.0900 (18)0.0600 (13)0.0012 (13)0.0003 (11)0.0162 (13)
Geometric parameters (Å, º) top
C1—O11.224 (3)C12—H12A0.9700
C1—N11.366 (3)C12—H12B0.9700
C1—N21.382 (3)C13—N31.465 (3)
C2—C31.378 (3)C13—C141.509 (4)
C2—N11.386 (3)C13—H13A0.9700
C2—C71.399 (3)C13—H13B0.9700
C3—C41.381 (3)C14—C151.514 (4)
C3—H30.9300C14—H14A0.9700
C4—C51.386 (4)C14—H14B0.9700
C4—Cl11.744 (3)C15—N41.449 (4)
C5—C61.380 (4)C15—H15A0.9700
C5—H50.9300C15—H15B0.9700
C6—C71.388 (3)C16—O21.232 (3)
C6—H60.9300C16—N51.359 (4)
C7—N21.394 (3)C16—N41.372 (4)
C8—N21.466 (3)C17—C181.375 (5)
C8—C101.518 (4)C17—C221.383 (5)
C8—C91.528 (4)C17—N51.388 (4)
C8—H80.9800C18—C191.390 (5)
C9—C111.521 (4)C18—H180.9300
C9—H9A0.9700C19—C201.359 (7)
C9—H9B0.9700C19—H190.9300
C10—C121.519 (4)C20—C211.396 (6)
C10—H10A0.9700C20—H200.9300
C10—H10B0.9700C21—C221.385 (4)
C11—N31.459 (3)C21—H210.9300
C11—H11A0.9700C22—N41.390 (4)
C11—H11B0.9700N1—H1N0.953 (10)
C12—N31.457 (4)N5—H5N0.951 (10)
O1—C1—N1127.3 (2)C14—C13—H13A109.3
O1—C1—N2125.8 (3)N3—C13—H13B109.3
N1—C1—N2106.8 (2)C14—C13—H13B109.3
C3—C2—N1130.7 (2)H13A—C13—H13B108.0
C3—C2—C7122.3 (2)C13—C14—C15112.2 (3)
N1—C2—C7106.9 (2)C13—C14—H14A109.2
C2—C3—C4116.6 (2)C15—C14—H14A109.2
C2—C3—H3121.7C13—C14—H14B109.2
C4—C3—H3121.7C15—C14—H14B109.2
C3—C4—C5122.3 (3)H14A—C14—H14B107.9
C3—C4—Cl1118.8 (2)N4—C15—C14113.8 (3)
C5—C4—Cl1118.9 (2)N4—C15—H15A108.8
C6—C5—C4120.6 (2)C14—C15—H15A108.8
C6—C5—H5119.7N4—C15—H15B108.8
C4—C5—H5119.7C14—C15—H15B108.8
C5—C6—C7118.4 (2)H15A—C15—H15B107.7
C5—C6—H6120.8O2—C16—N5127.5 (3)
C7—C6—H6120.8O2—C16—N4125.6 (3)
C6—C7—N2133.4 (2)N5—C16—N4106.9 (3)
C6—C7—C2119.8 (2)C18—C17—C22122.4 (3)
N2—C7—C2106.9 (2)C18—C17—N5131.1 (3)
N2—C8—C10111.5 (2)C22—C17—N5106.4 (3)
N2—C8—C9111.4 (2)C17—C18—C19116.4 (4)
C10—C8—C9111.4 (2)C17—C18—H18121.8
N2—C8—H8107.4C19—C18—H18121.8
C10—C8—H8107.4C20—C19—C18121.7 (4)
C9—C8—H8107.4C20—C19—H19119.2
C11—C9—C8112.2 (2)C18—C19—H19119.2
C11—C9—H9A109.2C19—C20—C21122.2 (4)
C8—C9—H9A109.2C19—C20—H20118.9
C11—C9—H9B109.2C21—C20—H20118.9
C8—C9—H9B109.2C22—C21—C20116.3 (4)
H9A—C9—H9B107.9C22—C21—H21121.9
C8—C10—C12111.0 (2)C20—C21—H21121.9
C8—C10—H10A109.4C17—C22—C21121.0 (4)
C12—C10—H10A109.4C17—C22—N4107.6 (3)
C8—C10—H10B109.4C21—C22—N4131.4 (4)
C12—C10—H10B109.4C1—N1—C2110.1 (2)
H10A—C10—H10B108.0C1—N1—H1N127 (2)
N3—C11—C9110.8 (2)C2—N1—H1N122 (2)
N3—C11—H11A109.5C1—N2—C7109.3 (2)
C9—C11—H11A109.5C1—N2—C8123.1 (2)
N3—C11—H11B109.5C7—N2—C8127.66 (19)
C9—C11—H11B109.5C12—N3—C11108.9 (2)
H11A—C11—H11B108.1C12—N3—C13111.4 (2)
N3—C12—C10110.4 (2)C11—N3—C13111.6 (2)
N3—C12—H12A109.6C16—N4—C22108.9 (3)
C10—C12—H12A109.6C16—N4—C15125.4 (3)
N3—C12—H12B109.6C22—N4—C15125.5 (3)
C10—C12—H12B109.6C16—N5—C17110.2 (3)
H12A—C12—H12B108.1C16—N5—H5N125 (2)
N3—C13—C14111.6 (2)C17—N5—H5N124 (2)
N3—C13—H13A109.3
N1—C2—C3—C4179.7 (3)C3—C2—N1—C1178.2 (3)
C7—C2—C3—C40.3 (4)C7—C2—N1—C11.8 (3)
C2—C3—C4—C51.8 (4)O1—C1—N2—C7179.6 (3)
C2—C3—C4—Cl1179.3 (2)N1—C1—N2—C70.2 (3)
C3—C4—C5—C61.6 (5)O1—C1—N2—C81.4 (5)
Cl1—C4—C5—C6179.5 (2)N1—C1—N2—C8178.0 (2)
C4—C5—C6—C70.6 (4)C6—C7—N2—C1177.9 (3)
C5—C6—C7—N2178.2 (3)C2—C7—N2—C11.3 (3)
C5—C6—C7—C22.7 (4)C6—C7—N2—C84.0 (5)
C3—C2—C7—C62.5 (4)C2—C7—N2—C8176.8 (3)
N1—C2—C7—C6177.4 (3)C10—C8—N2—C1110.7 (3)
C3—C2—C7—N2178.1 (3)C9—C8—N2—C1124.1 (3)
N1—C2—C7—N21.9 (3)C10—C8—N2—C771.4 (4)
N2—C8—C9—C11172.3 (2)C9—C8—N2—C753.7 (4)
C10—C8—C9—C1147.1 (3)C10—C12—N3—C1165.1 (3)
N2—C8—C10—C12174.0 (2)C10—C12—N3—C13171.4 (2)
C9—C8—C10—C1248.8 (3)C9—C11—N3—C1262.7 (3)
C8—C9—C11—N354.1 (3)C9—C11—N3—C13173.8 (2)
C8—C10—C12—N358.4 (3)C14—C13—N3—C1277.0 (3)
N3—C13—C14—C1568.2 (3)C14—C13—N3—C11161.0 (3)
C13—C14—C15—N4153.2 (3)O2—C16—N4—C22179.6 (3)
C22—C17—C18—C190.1 (5)N5—C16—N4—C220.9 (3)
N5—C17—C18—C19177.9 (3)O2—C16—N4—C154.0 (5)
C17—C18—C19—C200.2 (6)N5—C16—N4—C15174.8 (3)
C18—C19—C20—C210.3 (6)C17—C22—N4—C160.2 (3)
C19—C20—C21—C220.1 (6)C21—C22—N4—C16177.6 (3)
C18—C17—C22—C210.3 (5)C17—C22—N4—C15175.4 (3)
N5—C17—C22—C21178.6 (3)C21—C22—N4—C156.8 (5)
C18—C17—C22—N4177.7 (3)C14—C15—N4—C1689.7 (4)
N5—C17—C22—N40.5 (3)C14—C15—N4—C2285.3 (4)
C20—C21—C22—C170.2 (5)O2—C16—N5—C17180.0 (3)
C20—C21—C22—N4177.3 (3)N4—C16—N5—C171.2 (3)
O1—C1—N1—C2178.4 (3)C18—C17—N5—C16177.0 (3)
N2—C1—N1—C21.0 (3)C22—C17—N5—C161.1 (3)
(dom1suc1) top
Crystal data top
C22H25ClN5O2·C4H5O4Z = 2
Mr = 544.00F(000) = 572
Triclinic, P1Dx = 1.378 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3869 (15) ÅCell parameters from 25 reflections
b = 8.9838 (15) Åθ = 6–12°
c = 23.094 (7) ŵ = 0.20 mm1
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) Å3
Data collection top
Enraf-Nonius CAD4
diffractometer
3233 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ω scansh = 07
Absorption correction: ψ scan
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
k = 1010
Tmin = 0.897, Tmax = 0.966l = 2727
5090 measured reflections3 standard reflections every 300 min
4634 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0283P)2 + 1.3228P]
where P = (Fo2 + 2Fc2)/3
4634 reflections(Δ/σ)max < 0.001
439 parametersΔρmax = 0.28 e Å3
71 restraintsΔρmin = 0.26 e Å3
Crystal data top
C22H25ClN5O2·C4H5O4γ = 86.52 (3)°
Mr = 544.00V = 1311.4 (5) Å3
Triclinic, P1Z = 2
a = 6.3869 (15) ÅMo Kα radiation
b = 8.9838 (15) ŵ = 0.20 mm1
c = 23.094 (7) ÅT = 293 K
α = 89.89 (2)°0.65 × 0.30 × 0.18 mm
β = 82.52 (3)°
Data collection top
Enraf-Nonius CAD4
diffractometer
3233 reflections with I > 2σ(I)
Absorption correction: ψ scan
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Rint = 0.023
Tmin = 0.897, Tmax = 0.9663 standard reflections every 300 min
5090 measured reflections intensity decay: none
4634 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07071 restraints
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.28 e Å3
4634 reflectionsΔρmin = 0.26 e Å3
439 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.2954 (3)0.16562 (16)0.39061 (7)0.1145 (6)
C10.3180 (6)0.3837 (4)0.55504 (15)0.0516 (9)
C20.1093 (6)0.3075 (4)0.49069 (15)0.0529 (9)
C30.0091 (7)0.2840 (4)0.44244 (17)0.0671 (11)
H30.05550.32480.40630.081*
C40.1620 (7)0.1980 (5)0.4501 (2)0.0724 (12)
C50.2335 (6)0.1366 (5)0.5033 (2)0.0767 (13)
H50.35070.07910.50660.092*
C60.1317 (6)0.1600 (4)0.55222 (18)0.0646 (11)
H60.17840.11920.58830.078*
C70.0402 (5)0.2456 (4)0.54471 (15)0.0496 (9)
N10.2794 (5)0.3886 (3)0.49814 (12)0.0590 (8)
H10.35170.43600.47080.071*
N20.1730 (4)0.2912 (3)0.58357 (11)0.0490 (7)
C80.1556 (5)0.2558 (4)0.64600 (14)0.0444 (8)
H80.06710.17050.65260.053*
C90.0482 (5)0.3841 (4)0.68378 (15)0.0470 (8)
H9A0.13040.47130.67740.056*
H9B0.09110.40870.67270.056*
C100.3691 (5)0.2108 (4)0.66539 (14)0.0458 (8)
H10A0.43470.12660.64210.055*
H10B0.46110.29300.65900.055*
C110.0277 (5)0.3422 (4)0.74794 (14)0.0443 (8)
H11A0.03550.42650.77150.053*
H11B0.06460.26030.75490.053*
C120.3439 (5)0.1695 (3)0.72897 (14)0.0447 (8)
H12A0.25880.08360.73500.054*
H12B0.48160.14280.74070.054*
C130.2197 (6)0.2638 (4)0.82949 (15)0.0525 (9)
H13A0.14300.17430.83690.063*
H13B0.13790.34530.85090.063*
C140.4319 (6)0.2416 (4)0.85197 (16)0.0582 (10)
H14A0.50300.14940.83600.070*
H14B0.51890.32270.83830.070*
C150.4110 (7)0.2361 (5)0.91789 (18)0.0727 (12)
H15A0.54120.19760.93140.087*0.50
H15B0.29580.17650.93390.087*0.50
H15C0.30000.30720.93500.087*0.50
H15D0.54310.25730.93180.087*0.50
N30.2398 (4)0.2971 (3)0.76562 (12)0.0394 (6)
H3N0.331 (4)0.379 (2)0.7606 (13)0.047*
O10.4525 (4)0.4487 (3)0.57690 (11)0.0664 (8)
C230.4343 (5)0.6270 (4)0.76307 (16)0.0475 (8)
C240.5449 (5)0.7713 (4)0.75969 (18)0.0549 (10)
H24A0.49350.83220.72920.066*
H24B0.50640.82480.79630.066*
C250.7793 (5)0.7534 (4)0.7478 (2)0.0642 (11)
H25A0.81990.71870.70790.077*
H25B0.83020.67800.77360.077*
C260.8827 (6)0.8965 (4)0.7564 (2)0.0825 (16)
O30.5344 (4)0.5065 (2)0.75098 (12)0.0579 (7)
O40.2374 (4)0.6358 (3)0.78012 (13)0.0681 (8)
O50.8006 (5)1.0164 (3)0.7466 (2)0.152 (2)
O61.0627 (4)0.8887 (3)0.77679 (17)0.0874 (11)
H6O1.122 (7)0.788 (2)0.780 (2)0.105*
C16A0.1658 (9)0.4598 (7)0.9620 (3)0.0543 (18)0.50
C17A0.3724 (13)0.6554 (8)0.9465 (8)0.049 (3)0.50
C18A0.4571 (12)0.7928 (8)0.9445 (5)0.062 (3)0.50
H18A0.37790.87740.95970.074*0.50
C19A0.6645 (13)0.8001 (9)0.9192 (5)0.076 (3)0.50
H19A0.72450.89200.91620.091*0.50
C20A0.7844 (13)0.6742 (11)0.8983 (6)0.082 (4)0.50
H20A0.92520.68220.88290.098*0.50
C21A0.6983 (9)0.5351 (9)0.8999 (3)0.070 (2)0.50
H21A0.77730.45070.88440.084*0.50
C22A0.4919 (8)0.5276 (6)0.9252 (3)0.0527 (18)0.50
N4A0.3613 (8)0.4097 (5)0.9339 (2)0.0516 (14)0.50
N5A0.1768 (8)0.6102 (6)0.9697 (2)0.0543 (15)0.50
H5A0.07550.66850.98660.065*0.50
O2A0.0127 (8)0.3827 (6)0.9759 (2)0.0732 (16)0.50
C16B0.1493 (9)0.0310 (7)0.9565 (3)0.0542 (18)0.50
C17B0.3621 (10)0.1802 (7)0.9444 (5)0.048 (2)0.50
C18B0.4488 (14)0.3243 (8)0.9431 (9)0.065 (3)0.50
H18B0.36740.40360.95560.078*0.50
C19B0.6606 (13)0.3466 (9)0.9227 (4)0.081 (3)0.50
H19B0.72340.44290.92140.097*0.50
C20B0.7823 (13)0.2297 (10)0.9039 (7)0.086 (4)0.50
H20B0.92500.24860.89030.103*0.50
C21B0.6949 (9)0.0838 (8)0.9051 (3)0.069 (2)0.50
H21B0.77670.00480.89270.083*0.50
C22B0.4831 (8)0.0609 (6)0.9253 (3)0.0511 (17)0.50
N4B0.3495 (8)0.0670 (5)0.9326 (2)0.0516 (14)0.50
N5B0.1613 (8)0.1201 (6)0.9638 (2)0.0570 (16)0.50
H5B0.05770.17100.97850.068*0.50
O2B0.0057 (9)0.1194 (6)0.9679 (2)0.0724 (16)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1342 (13)0.1039 (10)0.1223 (12)0.0136 (9)0.0776 (10)0.0274 (9)
C10.056 (2)0.044 (2)0.055 (2)0.0097 (17)0.0077 (18)0.0033 (17)
C20.058 (2)0.042 (2)0.061 (2)0.0051 (17)0.0178 (19)0.0040 (17)
C30.082 (3)0.054 (2)0.068 (3)0.003 (2)0.021 (2)0.008 (2)
C40.074 (3)0.063 (3)0.086 (3)0.001 (2)0.036 (3)0.019 (2)
C50.056 (3)0.077 (3)0.102 (4)0.018 (2)0.023 (3)0.017 (3)
C60.049 (2)0.071 (3)0.075 (3)0.011 (2)0.007 (2)0.002 (2)
C70.0427 (19)0.046 (2)0.061 (2)0.0040 (16)0.0085 (17)0.0059 (17)
N10.071 (2)0.0589 (19)0.0500 (19)0.0190 (17)0.0124 (16)0.0077 (15)
N20.0454 (16)0.0514 (17)0.0508 (18)0.0131 (14)0.0042 (14)0.0026 (14)
C80.0429 (19)0.0392 (18)0.051 (2)0.0116 (15)0.0022 (15)0.0052 (15)
C90.0412 (19)0.0398 (18)0.059 (2)0.0006 (15)0.0060 (16)0.0056 (16)
C100.0403 (18)0.0413 (18)0.053 (2)0.0010 (15)0.0030 (15)0.0012 (16)
C110.0344 (17)0.0368 (18)0.060 (2)0.0007 (14)0.0004 (15)0.0003 (15)
C120.0403 (18)0.0291 (16)0.062 (2)0.0021 (14)0.0000 (16)0.0026 (15)
C130.053 (2)0.051 (2)0.050 (2)0.0008 (17)0.0031 (17)0.0071 (17)
C140.061 (2)0.056 (2)0.057 (2)0.0016 (19)0.0105 (19)0.0053 (18)
C150.073 (3)0.084 (3)0.062 (3)0.008 (2)0.018 (2)0.006 (2)
N30.0346 (14)0.0313 (14)0.0511 (16)0.0053 (11)0.0004 (12)0.0022 (12)
O10.0800 (19)0.0680 (17)0.0589 (16)0.0410 (15)0.0208 (14)0.0137 (13)
C230.0384 (19)0.0348 (18)0.073 (2)0.0085 (15)0.0172 (17)0.0089 (17)
C240.0361 (19)0.0346 (18)0.095 (3)0.0053 (15)0.0099 (18)0.0002 (18)
C250.0373 (19)0.0324 (18)0.120 (4)0.0031 (15)0.001 (2)0.003 (2)
C260.029 (2)0.033 (2)0.181 (5)0.0028 (16)0.002 (2)0.005 (2)
O30.0444 (14)0.0319 (13)0.097 (2)0.0057 (11)0.0085 (13)0.0030 (12)
O40.0332 (14)0.0455 (14)0.126 (2)0.0095 (11)0.0079 (14)0.0049 (15)
O50.0448 (18)0.0368 (17)0.377 (7)0.0056 (14)0.039 (3)0.035 (3)
O60.0400 (16)0.0422 (15)0.179 (3)0.0120 (12)0.0077 (18)0.0013 (19)
C16A0.049 (4)0.066 (5)0.046 (4)0.009 (4)0.007 (3)0.008 (4)
C17A0.045 (6)0.052 (5)0.049 (5)0.006 (4)0.008 (6)0.009 (4)
C18A0.066 (8)0.068 (7)0.054 (6)0.005 (6)0.017 (6)0.005 (5)
C19A0.079 (9)0.084 (8)0.069 (7)0.022 (6)0.024 (7)0.019 (6)
C20A0.055 (7)0.129 (12)0.065 (7)0.028 (7)0.007 (5)0.009 (8)
C21A0.046 (5)0.106 (7)0.057 (5)0.005 (5)0.004 (4)0.009 (5)
C22A0.047 (4)0.068 (5)0.042 (4)0.007 (4)0.007 (3)0.000 (3)
N4A0.052 (4)0.056 (4)0.046 (3)0.002 (3)0.005 (3)0.006 (3)
N5A0.047 (4)0.059 (4)0.054 (4)0.010 (3)0.001 (3)0.004 (3)
O2A0.055 (3)0.080 (4)0.081 (4)0.006 (3)0.004 (3)0.020 (3)
C16B0.052 (4)0.060 (5)0.049 (4)0.001 (4)0.001 (3)0.003 (4)
C17B0.046 (6)0.060 (5)0.040 (4)0.002 (4)0.010 (5)0.003 (4)
C18B0.064 (9)0.060 (7)0.072 (7)0.002 (6)0.014 (8)0.001 (6)
C19B0.075 (8)0.085 (8)0.083 (8)0.026 (6)0.024 (6)0.003 (6)
C20B0.065 (8)0.110 (11)0.081 (9)0.025 (8)0.018 (7)0.007 (9)
C21B0.053 (5)0.094 (7)0.062 (5)0.008 (5)0.013 (4)0.015 (5)
C22B0.051 (4)0.059 (5)0.045 (4)0.002 (4)0.011 (3)0.006 (3)
N4B0.056 (4)0.050 (3)0.048 (3)0.002 (3)0.003 (3)0.004 (3)
N5B0.056 (4)0.059 (4)0.055 (4)0.006 (3)0.000 (3)0.003 (3)
O2B0.066 (4)0.068 (4)0.078 (4)0.014 (3)0.003 (3)0.013 (3)
Geometric parameters (Å, º) top
Cl1—C41.742 (4)C23—C241.511 (4)
C1—O11.228 (4)C24—C251.486 (4)
C1—N11.368 (4)C24—H24A0.9700
C1—N21.384 (4)C24—H24B0.9700
C2—N11.374 (4)C25—C261.506 (5)
C2—C31.378 (4)C25—H25A0.9700
C2—C71.394 (5)C25—H25B0.9700
C3—C41.369 (5)C26—O51.202 (4)
C3—H30.9300C26—O61.297 (5)
C4—C51.380 (5)O6—H6O0.963 (10)
C5—C61.397 (5)C16A—O2A1.240 (7)
C5—H50.9300C16A—N5A1.371 (6)
C6—C71.371 (4)C16A—N4A1.381 (6)
C6—H60.9300C17A—C18A1.376 (7)
C7—N21.391 (4)C17A—N5A1.378 (7)
N1—H10.8600C17A—C22A1.393 (7)
N2—C81.467 (4)C18A—C19A1.382 (8)
C8—C91.520 (4)C18A—H18A0.9300
C8—C101.521 (4)C19A—C20A1.378 (8)
C8—H80.9800C19A—H19A0.9300
C9—C111.519 (4)C20A—C21A1.394 (8)
C9—H9A0.9700C20A—H20A0.9300
C9—H9B0.9700C21A—C22A1.376 (6)
C10—C121.504 (4)C21A—H21A0.9300
C10—H10A0.9700C22A—N4A1.385 (6)
C10—H10B0.9700N5A—H5A0.8600
C11—N31.497 (4)O2A—N5Ai1.627 (7)
C11—H11A0.9700C16B—O2B1.232 (7)
C11—H11B0.9700C16B—N5B1.367 (6)
C12—N31.496 (4)C16B—N4B1.382 (6)
C12—H12A0.9700C17B—C18B1.376 (7)
C12—H12B0.9700C17B—N5B1.380 (6)
C13—N31.495 (4)C17B—C22B1.396 (7)
C13—C141.515 (5)C18B—C19B1.377 (8)
C13—H13A0.9700C18B—H18B0.9300
C13—H13B0.9700C19B—C20B1.380 (8)
C14—C151.512 (5)C19B—H19B0.9300
C14—H14A0.9700C20B—C21B1.392 (8)
C14—H14B0.9700C20B—H20B0.9300
C15—N4A1.607 (6)C21B—C22B1.376 (6)
C15—H15A0.9700C21B—H21B0.9300
C15—H15B0.9700C22B—N4B1.386 (6)
N3—H3N0.966 (10)N5B—H5B0.8600
C23—O31.237 (4)O2B—N5Bii1.750 (7)
C23—O41.266 (4)
O1—C1—N1127.4 (3)C12—N3—C11110.8 (3)
O1—C1—N2126.5 (3)C13—N3—H3N104.7 (18)
N1—C1—N2106.1 (3)C12—N3—H3N108.1 (19)
N1—C2—C3131.6 (3)C11—N3—H3N110.2 (19)
N1—C2—C7106.9 (3)O3—C23—O4122.3 (3)
C3—C2—C7121.5 (3)O3—C23—C24120.9 (3)
C4—C3—C2116.9 (4)O4—C23—C24116.8 (3)
C4—C3—H3121.5C25—C24—C23114.7 (3)
C2—C3—H3121.5C25—C24—H24A108.6
C3—C4—C5122.4 (4)C23—C24—H24A108.6
C3—C4—Cl1118.8 (4)C25—C24—H24B108.6
C5—C4—Cl1118.7 (3)C23—C24—H24B108.6
C4—C5—C6120.7 (4)H24A—C24—H24B107.6
C4—C5—H5119.7C24—C25—C26112.4 (3)
C6—C5—H5119.7C24—C25—H25A109.1
C7—C6—C5117.1 (4)C26—C25—H25A109.1
C7—C6—H6121.5C24—C25—H25B109.1
C5—C6—H6121.5C26—C25—H25B109.1
C6—C7—N2131.7 (3)H25A—C25—H25B107.9
C6—C7—C2121.4 (3)O5—C26—O6119.7 (4)
N2—C7—C2106.9 (3)O5—C26—C25122.2 (4)
C1—N1—C2110.7 (3)O6—C26—C25118.1 (3)
C1—N1—H1124.7C26—O6—H6O114 (3)
C2—N1—H1124.7O2A—C16A—N5A128.2 (6)
C1—N2—C7109.3 (3)O2A—C16A—N4A126.1 (6)
C1—N2—C8124.6 (3)N5A—C16A—N4A105.7 (4)
C7—N2—C8125.9 (3)C18A—C17A—N5A131.7 (6)
N2—C8—C9112.0 (3)C18A—C17A—C22A121.6 (6)
N2—C8—C10112.3 (3)N5A—C17A—C22A106.6 (5)
C9—C8—C10109.8 (3)C17A—C18A—C19A117.4 (6)
N2—C8—H8107.5C17A—C18A—H18A121.3
C9—C8—H8107.5C19A—C18A—H18A121.3
C10—C8—H8107.5C20A—C19A—C18A121.5 (6)
C11—C9—C8110.6 (3)C20A—C19A—H19A119.3
C11—C9—H9A109.5C18A—C19A—H19A119.3
C8—C9—H9A109.5C19A—C20A—C21A121.1 (6)
C11—C9—H9B109.5C19A—C20A—H20A119.4
C8—C9—H9B109.5C21A—C20A—H20A119.4
H9A—C9—H9B108.1C22A—C21A—C20A117.4 (6)
C12—C10—C8110.7 (3)C22A—C21A—H21A121.3
C12—C10—H10A109.5C20A—C21A—H21A121.3
C8—C10—H10A109.5C21A—C22A—N4A132.1 (5)
C12—C10—H10B109.5C21A—C22A—C17A120.9 (5)
C8—C10—H10B109.5N4A—C22A—C17A107.0 (4)
H10A—C10—H10B108.1C16A—N4A—C22A109.8 (4)
N3—C11—C9110.7 (3)C16A—N4A—C15120.5 (4)
N3—C11—H11A109.5C22A—N4A—C15129.6 (4)
C9—C11—H11A109.5C16A—N5A—C17A110.7 (5)
N3—C11—H11B109.5C16A—N5A—H5A124.6
C9—C11—H11B109.5C17A—N5A—H5A124.6
H11A—C11—H11B108.1C16A—O2A—N5Ai133.0 (6)
N3—C12—C10110.4 (2)O2B—C16B—N5B128.3 (6)
N3—C12—H12A109.6O2B—C16B—N4B125.9 (6)
C10—C12—H12A109.6N5B—C16B—N4B105.8 (4)
N3—C12—H12B109.6C18B—C17B—N5B131.8 (6)
C10—C12—H12B109.6C18B—C17B—C22B121.6 (6)
H12A—C12—H12B108.1N5B—C17B—C22B106.6 (4)
N3—C13—C14112.8 (3)C17B—C18B—C19B117.4 (6)
N3—C13—H13A109.0C17B—C18B—H18B121.3
C14—C13—H13A109.0C19B—C18B—H18B121.3
N3—C13—H13B109.0C18B—C19B—C20B121.7 (6)
C14—C13—H13B109.0C18B—C19B—H19B119.2
H13A—C13—H13B107.8C20B—C19B—H19B119.2
C15—C14—C13112.5 (3)C19B—C20B—C21B121.0 (6)
C15—C14—H14A109.1C19B—C20B—H20B119.5
C13—C14—H14A109.1C21B—C20B—H20B119.5
C15—C14—H14B109.1C22B—C21B—C20B117.6 (6)
C13—C14—H14B109.1C22B—C21B—H21B121.2
H14A—C14—H14B107.8C20B—C21B—H21B121.2
C14—C15—N4A100.7 (3)C21B—C22B—N4B132.3 (5)
C14—C15—H15A111.6C21B—C22B—C17B120.8 (5)
N4A—C15—H15A111.6N4B—C22B—C17B106.9 (4)
C14—C15—H15B111.6C16B—N4B—C22B109.9 (4)
N4A—C15—H15B111.6C16B—N5B—C17B110.9 (5)
H15A—C15—H15B109.4C16B—N5B—H5B124.6
C13—N3—C12112.5 (2)C17B—N5B—H5B124.6
C13—N3—C11110.4 (2)C16B—O2B—N5Bii121.4 (5)
N1—C2—C3—C4178.7 (4)N5A—C17A—C18A—C19A177.9 (15)
C7—C2—C3—C40.4 (6)C22A—C17A—C18A—C19A2 (2)
C2—C3—C4—C50.1 (6)C17A—C18A—C19A—C20A2.0 (19)
C2—C3—C4—Cl1179.7 (3)C18A—C19A—C20A—C21A2.5 (19)
C3—C4—C5—C60.3 (7)C19A—C20A—C21A—C22A2.5 (16)
Cl1—C4—C5—C6179.8 (3)C20A—C21A—C22A—N4A179.8 (9)
C4—C5—C6—C70.0 (6)C20A—C21A—C22A—C17A2.1 (15)
C5—C6—C7—N2179.1 (4)C18A—C17A—C22A—C21A2 (2)
C5—C6—C7—C20.5 (6)N5A—C17A—C22A—C21A178.9 (9)
N1—C2—C7—C6178.6 (3)C18A—C17A—C22A—N4A179.7 (13)
C3—C2—C7—C60.7 (6)N5A—C17A—C22A—N4A2.6 (14)
N1—C2—C7—N20.3 (4)O2A—C16A—N4A—C22A179.4 (7)
C3—C2—C7—N2179.6 (3)N5A—C16A—N4A—C22A0.9 (8)
O1—C1—N1—C2176.8 (4)O2A—C16A—N4A—C152.3 (10)
N2—C1—N1—C22.6 (4)N5A—C16A—N4A—C15179.3 (5)
C3—C2—N1—C1177.7 (4)C21A—C22A—N4A—C16A179.5 (8)
C7—C2—N1—C11.5 (4)C17A—C22A—N4A—C16A2.2 (11)
O1—C1—N2—C7176.7 (4)C21A—C22A—N4A—C151.3 (12)
N1—C1—N2—C72.8 (4)C17A—C22A—N4A—C15179.6 (9)
O1—C1—N2—C80.4 (6)C14—C15—N4A—C16A112.6 (6)
N1—C1—N2—C8179.1 (3)C14—C15—N4A—C22A69.4 (7)
C6—C7—N2—C1176.9 (4)O2A—C16A—N5A—C17A177.7 (11)
C2—C7—N2—C11.9 (4)N4A—C16A—N5A—C17A0.8 (11)
C6—C7—N2—C80.6 (6)C18A—C17A—N5A—C16A178.8 (16)
C2—C7—N2—C8178.2 (3)C22A—C17A—N5A—C16A2.1 (15)
C1—N2—C8—C975.9 (4)N5A—C16A—O2A—N5Ai34.9 (13)
C7—N2—C8—C999.8 (4)N4A—C16A—O2A—N5Ai147.0 (6)
C1—N2—C8—C1048.1 (4)N5B—C17B—C18B—C19B177.4 (12)
C7—N2—C8—C10136.2 (3)C22B—C17B—C18B—C19B0 (2)
N2—C8—C9—C11178.5 (3)C17B—C18B—C19B—C20B0 (2)
C10—C8—C9—C1156.0 (3)C18B—C19B—C20B—C21B0 (2)
N2—C8—C10—C12177.7 (3)C19B—C20B—C21B—C22B0.4 (19)
C9—C8—C10—C1257.0 (3)C20B—C21B—C22B—N4B179.5 (10)
C8—C9—C11—N356.7 (3)C20B—C21B—C22B—C17B0.6 (14)
C8—C10—C12—N358.3 (3)C18B—C17B—C22B—C21B0.7 (17)
N3—C13—C14—C15169.5 (3)N5B—C17B—C22B—C21B177.6 (7)
C13—C14—C15—N4A75.8 (4)C18B—C17B—C22B—N4B179.8 (13)
C14—C13—N3—C1264.9 (4)N5B—C17B—C22B—N4B1.5 (10)
C14—C13—N3—C11170.8 (3)O2B—C16B—N4B—C22B179.5 (7)
C10—C12—N3—C13177.5 (3)N5B—C16B—N4B—C22B0.1 (8)
C10—C12—N3—C1158.5 (3)C21B—C22B—N4B—C16B178.0 (8)
C9—C11—N3—C13177.0 (3)C17B—C22B—N4B—C16B1.0 (9)
C9—C11—N3—C1257.7 (3)O2B—C16B—N5B—C17B178.5 (8)
O3—C23—C24—C256.7 (5)N4B—C16B—N5B—C17B0.9 (9)
O4—C23—C24—C25171.6 (4)C18B—C17B—N5B—C16B179.6 (15)
C23—C24—C25—C26168.9 (4)C22B—C17B—N5B—C16B1.5 (10)
C24—C25—C26—O532.4 (7)N5B—C16B—O2B—N5Bii50.2 (11)
C24—C25—C26—O6145.3 (4)N4B—C16B—O2B—N5Bii130.4 (7)
Symmetry codes: (i) x, y+1, z+2; (ii) x, y, z+2.

Experimental details

(dom1_p21c)(dom1suc1)
Crystal data
Chemical formulaC22H24ClN5O2C22H25ClN5O2·C4H5O4
Mr425.91544.00
Crystal system, space groupMonoclinic, P21/cTriclinic, P1
Temperature (K)293293
a, b, c (Å)20.214 (2), 6.8155 (9), 15.8630 (19)6.3869 (15), 8.9838 (15), 23.094 (7)
α, β, γ (°)90, 109.604 (9), 9089.89 (2), 82.52 (3), 86.52 (3)
V3)2058.7 (4)1311.4 (5)
Z42
Radiation typeMo KαMo Kα
µ (mm1)0.220.20
Crystal size (mm)0.6 × 0.45 × 0.30.65 × 0.30 × 0.18
Data collection
DiffractometerEnraf-Nonius CAD4
diffractometer
Enraf-Nonius CAD4
diffractometer
Absorption correctionψ scan
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
ψ scan
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Tmin, Tmax0.943, 0.9990.897, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
3791, 3639, 2207 5090, 4634, 3233
Rint0.0160.023
(sin θ/λ)max1)0.5960.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.117, 1.01 0.070, 0.151, 1.10
No. of reflections36394634
No. of parameters277439
No. of restraints271
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.190.28, 0.26

Computer programs: CAD-4 EXPRESS (Enraf Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), WinGX publication routines (Farrugia, 1999).

 

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