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The metabolism of all-trans-retinoic acid is mediated by a cytochrome dependent P-450 system. The title compound, C21H23N5S, is an inhibitor of the P-450 system. Two planar rings connected via a central CH group form a dihedral angle of 80.2 (1)°; the planar systems connected through an NH group form a dihedral angle of 37.12 (8)°. The N—H...N hydrogen bonds link the mol­ecules of the title compound into infinite chains stretching along the c direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011230/ya6034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011230/ya6034Isup2.hkl
Contains datablock I

CCDC reference: 170905

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.049
  • wR factor = 0.145
  • Data-to-parameter ratio = 13.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
RADNW_01 Alert C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 1.54175-1.54180 Wavelength given = 1.54184 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 69.18 From the CIF: _reflns_number_total 3370 From the CIF: _diffrn_reflns_limit_ max hkl 9. 16. 19. From the CIF: _diffrn_reflns_limit_ min hkl -9. -16. -19. TEST1: Expected hkl limits for theta max Calculated maximum hkl 11. 16. 19. Calculated minimum hkl -11. -16. -19. ALERT: Expected hkl max differ from CIF values REFLT_03 From the CIF: _diffrn_reflns_theta_max 69.18 From the CIF: _reflns_number_total 3370 Count of symmetry unique reflns 2176 Completeness (_total/calc) 154.87% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1194 Fraction of Friedel pairs measured 0.549 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

All-trans-retinoic-acid (ATRA) is a metabolite of retinol (Vitamin A) which is involved in growth and epithelial differentiation in mammals. However the potency of ATRA is strongly attenuated by its rapid metabolism involving the stage of hydroxylation, mediated by a cytochrome dependent P-450 system (Leo et al., 1989). The P-450 system is inhibited by the title compound, which leads to increased plasma levels of ATRA.

All four rings in the molecule of the title compound (Fig. 1) are essentially planar. The imidazolyl ring is almost perpendicular to the phenylene ring [dihedral angle 80.2 (1)°], the phenylene ring and the benzothiazolyl ring are twisted with a dihedral angle of 37.12 (8)°. The secondary amine group is almost coplanar with the benzothiazolyl moiety [dihedral angle 4.3 (2)°] but is twisted with respect to the phenylene ring [dihedral angle 37.3 (3)°]. The degree of coplanarity and conjugation with the π-electron systems of the aromatic rings is reflected in the C—N bond lengths. The C19—N18 bond [1.357 (4)°] is significantly shorter than the C15—N18 bond [1.411 (4)°].

The N18—H18···N9 hydrogen bond [N18—H18···N9i 2.07 Å, N18···N9i 2.884 (4) Å, N18—H18···N9i 158 ° (D—H distance not normalized); symmetry code (i): 1/2 - x, 1 - y, z - 1/2] links two molecules related by the 21(z) screw axis, thus giving rise to infinite one-dimensional chains stretching along the c axis of the crystal.

Experimental top

The title compound was obtained from the Janssen Research Foundation, Beerse, Belgium. The synthesis has been described by Venet et al. (1997). Single crystals were grown by slow evaporation from a solution in ethanol.

Refinement top

After checking their presence in the difference map, H atoms were placed at their geometrically calculated positions (the NH group has a planar environment), except for those of the methyl groups. The latter were found from a circular difference Fourier synthesis. All H atoms were allowed to ride on their parent atom and for the methyl groups to rotate around their local threefold axis. The isotropic displacement factors were fixed at 1.25 Ueq of their parent atoms.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PARST (Nardelli, 1983).

Figures top
[Figure 1] Fig. 1. Perspective view of a molecule of the title compound with atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
N-{4-[(1S,2S)-2-(Dimethylamino)-1-(1H-imidazol-1-yl)propyl]phenyl}- 2-benzothiazolamine top
Crystal data top
C21H23N5SDx = 1.232 Mg m3
Mr = 377.51Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 37 reflections
a = 9.4442 (9) Åθ = 5.6–26.6°
b = 13.725 (1) ŵ = 1.52 mm1
c = 15.703 (1) ÅT = 293 K
V = 2035.4 (3) Å3Prism, colourless
Z = 40.30 × 0.24 × 0.08 mm
F(000) = 800
Data collection top
Siemens P4 four-circle
diffractometer
Rint = 0.023
ω/2θ scanθmax = 69.2°
Absorption correction: ψ scan
XEMP (Siemens, 1989)
h = 99
Tmin = 0.625, Tmax = 0.886k = 1616
3908 measured reflectionsl = 1919
3370 independent reflections3 standard reflections every 100 reflections
2912 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0806P)2 + 0.5545P]
where P = (Fo2 + 2Fc2)/3
Least-squares matrix: full(Δ/σ)max = 0.001
R[F2 > 2σ(F2)] = 0.049Δρmax = 0.17 e Å3
wR(F2) = 0.145Δρmin = 0.18 e Å3
S = 1.07Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin((2θ)]-1/4
3370 reflectionsExtinction coefficient: 0.0023 (4)
248 parametersAbsolute structure: Flack (1983). 847 Friedel pairs.
H-atom parameters constrainedAbsolute structure parameter: 0.01 (3)
Crystal data top
C21H23N5SV = 2035.4 (3) Å3
Mr = 377.51Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 9.4442 (9) ŵ = 1.52 mm1
b = 13.725 (1) ÅT = 293 K
c = 15.703 (1) Å0.30 × 0.24 × 0.08 mm
Data collection top
Siemens P4 four-circle
diffractometer
2912 reflections with I > 2σ(I)
Absorption correction: ψ scan
XEMP (Siemens, 1989)
Rint = 0.023
Tmin = 0.625, Tmax = 0.8863 standard reflections every 100 reflections
3908 measured reflections intensity decay: none
3370 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.145Δρmax = 0.17 e Å3
S = 1.07Δρmin = 0.18 e Å3
3370 reflectionsAbsolute structure: Flack (1983). 847 Friedel pairs.
248 parametersAbsolute structure parameter: 0.01 (3)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.1766 (4)0.1146 (2)0.8725 (2)0.066 (1)*
C20.0559 (7)0.0493 (4)0.8739 (4)0.125 (3)*
C30.2986 (6)0.0693 (4)0.9117 (3)0.103 (2)*
C40.2092 (5)0.1578 (2)0.7885 (2)0.062 (1)*
C50.2273 (8)0.0851 (3)0.7160 (3)0.114 (2)*
C60.0959 (4)0.2346 (2)0.7671 (2)0.0520 (9)*
N70.0937 (3)0.3121 (2)0.8318 (2)0.0506 (8)*
C80.2038 (4)0.3508 (3)0.8740 (2)0.062 (1)*
N90.1679 (4)0.4273 (2)0.9196 (2)0.064 (1)*
C100.0262 (5)0.4375 (3)0.9061 (2)0.072 (2)*
C110.0211 (4)0.3677 (3)0.8520 (3)0.068 (1)*
C120.1127 (4)0.2780 (2)0.6789 (2)0.050 (1)*
C130.2216 (4)0.3422 (2)0.6600 (2)0.059 (1)*
C140.2385 (4)0.3791 (2)0.5791 (2)0.058 (1)*
C150.1489 (4)0.3521 (2)0.5141 (2)0.054 (1)*
C160.0402 (5)0.2875 (3)0.5310 (2)0.069 (1)*
C170.0230 (4)0.2514 (3)0.6135 (2)0.067 (1)*
N180.1695 (3)0.3955 (2)0.4336 (2)0.063 (1)*
C190.1512 (4)0.3510 (2)0.3572 (2)0.054 (1)*
S200.1975 (1)0.41953 (6)0.26549 (5)0.0671 (3)*
C210.1544 (4)0.3181 (3)0.2044 (2)0.057 (1)*
C220.1602 (5)0.3069 (3)0.1163 (2)0.070 (1)*
C230.1221 (5)0.2184 (3)0.0815 (2)0.074 (1)*
C240.0790 (4)0.1427 (3)0.1330 (2)0.071 (1)*
C250.0726 (4)0.1533 (3)0.2208 (2)0.063 (1)*
C260.1093 (4)0.2421 (2)0.2570 (2)0.053 (1)*
N270.1075 (3)0.2622 (2)0.3444 (2)0.0567 (9)*
H2A0.03900.02800.93120.157*
H2B0.07500.00610.83840.157*
H2C0.02620.08290.85290.157*
H3A0.27360.04630.96750.129*
H3B0.37370.11610.91630.129*
H3C0.32940.01540.87740.129*
H40.29930.19250.79440.077*
H5A0.29030.03400.73360.143*
H5B0.26630.11780.66730.143*
H5C0.13700.05780.70150.143*
H60.00370.20190.76890.065*
H80.29540.32620.87130.077*
H100.03010.48560.93050.090*
H110.11330.35950.83260.085*
H130.28440.36070.70270.074*
H140.31150.42290.56810.072*
H160.02090.26820.48770.086*
H170.05080.20840.62470.083*
H180.19610.45540.43290.079*
H220.18920.35810.08160.087*
H230.12560.20970.02280.092*
H240.05370.08350.10850.088*
H250.04410.10160.25500.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.081 (2)0.058 (2)0.059 (2)0.006 (2)0.012 (2)0.009 (1)
C20.149 (5)0.112 (4)0.115 (4)0.063 (4)0.047 (4)0.058 (3)
C30.114 (4)0.109 (3)0.086 (3)0.019 (4)0.016 (3)0.023 (3)
C40.080 (3)0.053 (2)0.052 (2)0.000 (2)0.000 (2)0.001 (1)
C50.198 (6)0.074 (3)0.071 (3)0.041 (4)0.014 (3)0.013 (2)
C60.061 (2)0.049 (1)0.046 (1)0.010 (1)0.002 (2)0.002 (1)
N70.057 (2)0.050 (1)0.045 (1)0.007 (1)0.003 (1)0.001 (1)
C80.063 (2)0.064 (2)0.059 (2)0.006 (2)0.001 (2)0.009 (2)
N90.086 (3)0.056 (1)0.050 (1)0.011 (2)0.004 (1)0.005 (1)
C100.089 (3)0.064 (2)0.061 (2)0.008 (2)0.020 (2)0.004 (2)
C110.059 (2)0.071 (2)0.073 (2)0.000 (2)0.008 (2)0.002 (2)
C120.056 (2)0.048 (2)0.047 (2)0.008 (1)0.001 (1)0.001 (1)
C130.066 (2)0.061 (2)0.050 (2)0.016 (2)0.007 (2)0.003 (1)
C140.065 (2)0.055 (2)0.054 (2)0.014 (2)0.002 (2)0.002 (1)
C150.068 (2)0.051 (2)0.043 (2)0.003 (2)0.004 (1)0.001 (1)
C160.078 (3)0.084 (2)0.045 (2)0.025 (2)0.007 (2)0.004 (2)
C170.072 (3)0.077 (2)0.050 (2)0.028 (2)0.001 (2)0.004 (2)
N180.087 (2)0.056 (1)0.046 (1)0.012 (2)0.000 (1)0.003 (1)
C190.061 (2)0.053 (2)0.048 (2)0.001 (2)0.003 (1)0.002 (1)
S200.0939 (7)0.0577 (4)0.0497 (4)0.0013 (5)0.0044 (4)0.0080 (3)
C210.060 (2)0.062 (2)0.049 (2)0.009 (2)0.002 (2)0.003 (1)
C220.083 (3)0.078 (2)0.049 (2)0.010 (2)0.001 (2)0.005 (2)
C230.079 (3)0.092 (3)0.050 (2)0.011 (2)0.004 (2)0.006 (2)
C240.066 (2)0.080 (2)0.066 (2)0.007 (2)0.007 (2)0.021 (2)
C250.061 (2)0.064 (2)0.064 (2)0.001 (2)0.004 (2)0.005 (2)
C260.051 (2)0.058 (2)0.049 (2)0.005 (1)0.002 (1)0.000 (1)
N270.063 (2)0.058 (2)0.049 (1)0.000 (1)0.002 (1)0.001 (1)
Geometric parameters (Å, º) top
N1—C21.449 (7)C12—C171.379 (5)
N1—C31.447 (6)C13—C141.378 (5)
N1—C41.480 (4)C13—H130.930
C2—H2A0.960C14—C151.376 (5)
C2—H2B0.960C14—H140.930
C2—H2C0.960C15—C161.382 (5)
C3—H3A0.960C15—N181.411 (4)
C3—H3B0.960C16—C171.397 (5)
C3—H3C0.960C16—H160.930
C4—C51.523 (6)C17—H170.930
C4—C61.539 (5)N18—C191.357 (4)
C4—H40.980N18—H180.860
C5—H5A0.960C19—S201.775 (3)
C5—H5B0.960C19—N271.303 (4)
C5—H5C0.960S20—C211.739 (4)
C6—N71.472 (4)C21—C221.393 (5)
C6—C121.517 (4)C21—C261.397 (5)
C6—H60.980C22—C231.380 (6)
N7—C81.342 (5)C22—H220.930
N7—C111.363 (5)C23—C241.378 (6)
C8—N91.316 (5)C23—H230.930
C8—H80.930C24—C251.388 (5)
N9—C101.362 (6)C24—H240.930
C10—C111.356 (6)C25—C261.389 (5)
C10—H100.930C25—H250.930
C11—H110.930C26—N271.401 (4)
C12—C131.387 (5)
C2—N1—C3110.8 (4)C10—C11—H11126.9
C2—N1—C4115.1 (3)C6—C12—C13121.5 (3)
C3—N1—C4112.7 (3)C6—C12—C17120.8 (3)
N1—C2—H2A109.5C13—C12—C17117.7 (3)
N1—C2—H2B109.5C12—C13—C14121.1 (3)
N1—C2—H2C109.5C12—C13—H13119.4
H2A—C2—H2B109.5C14—C13—H13119.4
H2A—C2—H2C109.5C13—C14—C15120.9 (3)
H2B—C2—H2C109.5C13—C14—H14119.6
N1—C3—H3A109.5C15—C14—H14119.6
N1—C3—H3B109.5C14—C15—C16119.2 (3)
N1—C3—H3C109.5C14—C15—N18117.7 (3)
H3A—C3—H3B109.5C16—C15—N18123.0 (3)
H3A—C3—H3C109.5C15—C16—C17119.4 (3)
H3B—C3—H3C109.5C15—C16—H16120.3
N1—C4—C5115.3 (3)C17—C16—H16120.3
N1—C4—C6108.9 (3)C12—C17—C16121.7 (3)
N1—C4—H4106.9C12—C17—H17119.2
C5—C4—C6111.3 (3)C16—C17—H17119.2
C5—C4—H4106.9C15—N18—C19125.8 (3)
C6—C4—H4106.9C15—N18—H18117.1
C4—C5—H5A109.5C19—N18—H18117.1
C4—C5—H5B109.5N18—C19—S20116.6 (2)
C4—C5—H5C109.5N18—C19—N27126.7 (3)
H5A—C5—H5B109.5S20—C19—N27116.7 (2)
H5A—C5—H5C109.5C19—S20—C2188.1 (2)
H5B—C5—H5C109.5S20—C21—C22128.8 (3)
C4—C6—N7110.8 (2)S20—C21—C26110.0 (3)
C4—C6—C12113.3 (3)C22—C21—C26121.2 (3)
C4—C6—H6107.4C21—C22—C23118.7 (3)
N7—C6—C12110.4 (2)C21—C22—H22120.7
N7—C6—H6107.4C23—C22—H22120.7
C12—C6—H6107.4C22—C23—C24120.6 (4)
C6—N7—C8128.0 (3)C22—C23—H23119.7
C6—N7—C11125.2 (3)C24—C23—H23119.7
C8—N7—C11106.3 (3)C23—C24—C25121.1 (3)
N7—C8—N9112.6 (3)C23—C24—H24119.4
N7—C8—H8123.7C25—C24—H24119.4
N9—C8—H8123.7C24—C25—C26119.2 (3)
C8—N9—C10104.5 (3)C24—C25—H25120.4
N9—C10—C11110.4 (4)C26—C25—H25120.4
N9—C10—H10124.8C21—C26—C25119.3 (3)
C11—C10—H10124.8C21—C26—N27115.9 (3)
N7—C11—C10106.2 (3)C25—C26—N27124.8 (3)
N7—C11—H11126.9C19—N27—C26109.3 (3)
C3—N1—C2—H2A54.2C6—C12—C13—C14178.1 (3)
C3—N1—C2—H2B65.8C6—C12—C13—H131.9
C3—N1—C2—H2C174.2C17—C12—C13—C140.8 (5)
C4—N1—C2—H2A176.5C17—C12—C13—H13179.2
C4—N1—C2—H2B63.5C6—C12—C17—C16177.4 (3)
C4—N1—C2—H2C56.5C6—C12—C17—H172.6
C2—N1—C3—H3A53.2C13—C12—C17—C160.0 (5)
C2—N1—C3—H3B173.2C13—C12—C17—H17180.0
C2—N1—C3—H3C66.8C12—C13—C14—C151.0 (5)
C4—N1—C3—H3A176.2C12—C13—C14—H14179.0
C4—N1—C3—H3B56.2H13—C13—C14—C15179.0
C4—N1—C3—H3C63.8H13—C13—C14—H141.0
C2—N1—C4—C553.5 (5)C13—C14—C15—C160.4 (5)
C2—N1—C4—C672.5 (4)C13—C14—C15—N18177.8 (3)
C2—N1—C4—H4172.3H14—C14—C15—C16179.6
C3—N1—C4—C574.8 (4)H14—C14—C15—N182.2
C3—N1—C4—C6159.2 (3)C14—C15—C16—C170.4 (5)
C3—N1—C4—H443.9C14—C15—C16—H16179.6
N1—C4—C5—H5A48.7N18—C15—C16—C17176.9 (3)
N1—C4—C5—H5B168.6N18—C15—C16—H163.1
N1—C4—C5—H5C71.4C14—C15—N18—C19144.2 (3)
C6—C4—C5—H5A173.4C14—C15—N18—H1835.8
C6—C4—C5—H5B66.6C16—C15—N18—C1938.5 (5)
C6—C4—C5—H5C53.4C16—C15—N18—H18141.5
H4—C4—C5—H5A70.1C15—C16—C17—C120.6 (6)
H4—C4—C5—H5B49.9C15—C16—C17—H17179.4
H4—C4—C5—H5C169.9H16—C16—C17—C12179.4
N1—C4—C6—N759.8 (3)H16—C16—C17—H170.6
N1—C4—C6—C12175.4 (3)C15—N18—C19—S20175.3 (3)
N1—C4—C6—H657.1C15—N18—C19—N272.3 (5)
C5—C4—C6—N7171.9 (3)H18—N18—C19—S204.7
C5—C4—C6—C1247.2 (4)H18—N18—C19—N27177.7
C5—C4—C6—H671.2N18—C19—S20—C21177.6 (3)
H4—C4—C6—N755.4N27—C19—S20—C210.3 (3)
H4—C4—C6—C1269.3N18—C19—N27—C26177.2 (3)
H4—C4—C6—H6172.3S20—C19—N27—C260.5 (4)
C4—C6—N7—C836.3 (4)C19—S20—C21—C22180.0 (4)
C4—C6—N7—C11153.1 (3)C19—S20—C21—C260.1 (3)
C12—C6—N7—C890.0 (4)S20—C21—C22—C23179.2 (3)
C12—C6—N7—C1180.5 (4)S20—C21—C22—H220.8
H6—C6—N7—C8153.3C26—C21—C22—C230.9 (6)
H6—C6—N7—C1136.2C26—C21—C22—H22179.1
C4—C6—C12—C1372.1 (4)S20—C21—C26—C25178.6 (3)
C4—C6—C12—C17105.1 (4)S20—C21—C26—N270.2 (4)
N7—C6—C12—C1352.8 (4)C22—C21—C26—C251.4 (5)
N7—C6—C12—C17130.0 (3)C22—C21—C26—N27179.8 (3)
H6—C6—C12—C13169.5C21—C22—C23—C240.1 (6)
H6—C6—C12—C1713.2C21—C22—C23—H23179.9
C6—N7—C8—N9171.8 (3)H22—C22—C23—C24179.9
C6—N7—C8—H88.2H22—C22—C23—H230.1
C11—N7—C8—N90.1 (4)C22—C23—C24—C250.0 (6)
C11—N7—C8—H8179.9C22—C23—C24—H24180.0
C6—N7—C11—C10172.5 (3)H23—C23—C24—C25180.0
C6—N7—C11—H117.5H23—C23—C24—H240.0
C8—N7—C11—C100.3 (4)C23—C24—C25—C260.6 (6)
C8—N7—C11—H11179.8C23—C24—C25—H25179.4
N7—C8—N9—C100.4 (4)H24—C24—C25—C26179.4
H8—C8—N9—C10179.6H24—C24—C25—H250.6
C8—N9—C10—C110.6 (4)C24—C25—C26—C211.3 (5)
C8—N9—C10—H10179.4C24—C25—C26—N27180.0 (3)
N9—C10—C11—N70.5 (4)H25—C25—C26—C21178.7
N9—C10—C11—H11179.5H25—C25—C26—N270.1
H10—C10—C11—N7179.5C21—C26—N27—C190.4 (4)
H10—C10—C11—H110.5C25—C26—N27—C19178.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N18—H18···N9i0.862.072.884 (4)158
C22—H22···N9ii0.932.723.503 (5)142
C23—H23···N1ii0.932.743.614 (5)157
Symmetry codes: (i) x+1/2, y+1, z1/2; (ii) x, y, z1.

Experimental details

Crystal data
Chemical formulaC21H23N5S
Mr377.51
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)9.4442 (9), 13.725 (1), 15.703 (1)
V3)2035.4 (3)
Z4
Radiation typeCu Kα
µ (mm1)1.52
Crystal size (mm)0.30 × 0.24 × 0.08
Data collection
DiffractometerSiemens P4 four-circle
diffractometer
Absorption correctionψ scan
XEMP (Siemens, 1989)
Tmin, Tmax0.625, 0.886
No. of measured, independent and
observed [I > 2σ(I)] reflections
3908, 3370, 2912
Rint0.023
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.145, 1.07
No. of reflections3370
No. of parameters248
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.18
Absolute structureFlack (1983). 847 Friedel pairs.
Absolute structure parameter0.01 (3)

Computer programs: XSCANS (Siemens, 1996), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), DIAMOND (Bergerhoff, 1996), PARST (Nardelli, 1983).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N18—H18···N9i0.862.072.884 (4)158
C22—H22···N9ii0.932.723.503 (5)142
C23—H23···N1ii0.932.743.614 (5)157
Symmetry codes: (i) x+1/2, y+1, z1/2; (ii) x, y, z1.
 

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