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Acta Cryst. (2001). E57, o655-o656
https://doi.org/10.1107/S1600536801010315
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(R)-1-{(2-Oxo-1,2-di­hydro­quinolin-6-yl)[3-(tri­fluoro­methyl)­phenyl]­methyl}-1H-1,2,4-triazol-4-ium bromide

O. M. Peeters, N. M. Blaton and C. J. De Ranter
The metabolism of all-trans-retinoic acid is mediated by a cytochrome dependent P-450 system. The title compound, C19H14F3N4O+·Br− (R111214), is an inhibitor of P-450. The three planar ring systems, viz. the triazolyl, phenyl and quinolinone groups, are arranged in a propeller-like fashion around the central CH group. The dihedral angles formed by the triazolyl/phenyl, triazolyl/quinolinone and phenyl/quinolinone planes are 55.8 (1), 79.85 (9) and 78.49 (9)°, respectively. The N—H...O hydrogen bonds, involving the triazolium N—H group and the quinolinone O atom, link the cations into infinite chains stretching along the c axis of the crystal.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801010315/ya6033sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801010315/ya6033Isup2.hkl
Contains datablock I

CCDC reference: 170787

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.034
  • wR factor = 0.064
  • Data-to-parameter ratio = 12.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:



PLAT_301  Alert C Main Residue Disorder ........................      13.00 Perc.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.10
         From the CIF: _reflns_number_total               3463
         Count of symmetry unique reflns         2017
         Completeness (_total/calc)            171.69%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1446
         Fraction of Friedel pairs measured     0.717
         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, (I), which leads to increased plasma levels of ATRA.

The title compound has a propeller-like conformation (Fig. 1). The triazolyl and phenyl rings form an interplanar angle of 55.8 (1)° and the dihedral angles between these rings and the quinolinone moiety are 79.85 (9) and 78.49 (9)°, respectively. The small tilt between the planes of the six-membered rings in the quinolinone moiety is 1.67 (9)°. The bromide anion is hydrogen bonded to the quinolinone N atom. The N—H···O hydrogen bonds between the protonated nitrogen of the triazolyl ring and the quinolinone O atom link the cations into infinite chains stretching along the c axis of the crystal. Weaker C—H···Br and C—H···O hydrogen bonds also contribute to the stability of the crystalline product. Details of the hydrogen bonding geometry (D—H distances were not normalized) are given in Table 1.

Experimental top

The title compound was obtained from the Janssen Research Foundation, Beerse, Belgium. The synthesis has been described by Venet et al. (1996). Single crystals were grown by slow evaporation from a solution in ethanol.

Refinement top

After checking their presence in the difference map (which, in particular, unambiguously confirmed the protonation of the N1 and N16 atoms), H atoms were placed in the geometrically calculated positions. All H atoms were allowed to ride on their parent atom. The isotropic displacement parameters were fixed at 1.2Ueq of their parent atoms. The CF3 group shows a rotational disorder. It was modelled by two CF3 groups with an occupation factor of 0.5 and refined using distance restraints.

Computing details top

Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); 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 the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The alternative position of the disordered CF3 group is not shown.
(R)-1-{(2-Oxo-1,2-dihydroquinolin-6-yl)[3-(trifluoromethyl)phenyl]methyl}- 1H-1,2,4-triazol-4-ium bromide top
Crystal data top
C19H14F3N4O+·Br−Dx = 1.538 Mg m−3
Dm = 1.525 Mg m−3
Dm measured by flotation in CCl4/n-heptane
Mr = 451.25Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 24 reflections
a = 7.058 (4) Åθ = 7.5–11.0°
b = 16.212 (8) ŵ = 2.15 mm−1
c = 17.029 (9) ÅT = 293 K
V = 1949 (2) Å3Block, colourless
Z = 40.50 × 0.30 × 0.30 mm
F(000) = 904
Data collection top
Stoe Stadi-4 four-circle
diffractometer		Rint = 0.029
ω scansθmax = 25.1°
Absorption correction: ψ scan
(EMPIR; Stoe & Cie, 1992)		h = −8→8
Tmin = 0.427, Tmax = 0.525k = −19→19
5505 measured reflectionsl = −20→20
3463 independent reflections3 standard reflections every 60 min
2660 reflections with I > 2σ(I) intensity decay: 5.0%
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.024P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.034(Δ/σ)max = 0.001
wR(F2) = 0.064Δρmax = 0.21 e Å−3
S = 1.04Δρmin = −0.22 e Å−3
3463 reflectionsAbsolute structure: Flack (1983), 1457 Friedel pairs
289 parametersAbsolute structure parameter: 0.000 (9)
Crystal data top
C19H14F3N4O+·Br−V = 1949 (2) Å3
Mr = 451.25Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.058 (4) ŵ = 2.15 mm−1
b = 16.212 (8) ÅT = 293 K
c = 17.029 (9) Å0.50 × 0.30 × 0.30 mm
Data collection top
Stoe Stadi-4 four-circle
diffractometer		2660 reflections with I > 2σ(I)
Absorption correction: ψ scan
(EMPIR; Stoe & Cie, 1992)		Rint = 0.029
Tmin = 0.427, Tmax = 0.5253 standard reflections every 60 min
5505 measured reflections intensity decay: 5.0%
3463 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.064Δρmax = 0.21 e Å−3
S = 1.04Δρmin = −0.22 e Å−3
3463 reflectionsAbsolute structure: Flack (1983), 1457 Friedel pairs
289 parametersAbsolute structure parameter: 0.000 (9)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br0.45252 (5)1.10851 (2)0.41140 (2)0.0535 (1)*
N10.2842 (4)1.0773 (2)0.5893 (2)0.0434 (9)*
C20.1134 (5)1.1068 (2)0.6127 (2)0.048 (1)*
C30.0385 (7)1.0728 (2)0.6841 (2)0.057 (1)*
C40.1324 (6)1.0157 (2)0.7245 (2)0.056 (1)*
C50.3106 (5)0.9852 (2)0.6979 (2)0.042 (1)*
C60.4113 (5)0.9232 (2)0.7376 (2)0.046 (1)*
C70.5804 (5)0.8941 (2)0.7093 (2)0.041 (1)*
C80.6521 (5)0.9279 (2)0.6395 (2)0.047 (1)*
C90.5575 (6)0.9889 (2)0.6004 (2)0.048 (1)*
C100.3846 (5)1.0175 (2)0.6292 (2)0.039 (1)*
O110.0312 (4)1.1609 (2)0.5738 (1)0.064 (1)*
C120.6953 (5)0.8275 (2)0.7502 (2)0.044 (1)*
N130.5872 (4)0.7932 (2)0.8170 (2)0.0384 (9)*
N140.4368 (5)0.7405 (2)0.8069 (2)0.050 (1)*
C150.3699 (6)0.7333 (2)0.8779 (2)0.054 (1)*
N160.4703 (4)0.7775 (2)0.9302 (2)0.048 (1)*
C170.6034 (5)0.8156 (2)0.8901 (2)0.047 (1)*
C180.7636 (5)0.7612 (2)0.6948 (2)0.050 (1)*
C190.6417 (6)0.7213 (2)0.6449 (2)0.060 (2)*
C200.7065 (7)0.6616 (3)0.5940 (3)0.070 (2)*
C210.8946 (7)0.6420 (3)0.5925 (3)0.089 (2)*
C221.0170 (7)0.6816 (3)0.6416 (3)0.090 (2)*
C230.9533 (7)0.7409 (3)0.6928 (2)0.068 (2)*
C24A0.582 (2)0.621 (1)0.534 (1)0.080 (7)*.5
F25A0.647 (3)0.6300 (8)0.4607 (7)0.161 (7)*.5
F26A0.408 (2)0.649 (2)0.534 (1)0.137 (7)*.5
F27A0.561 (3)0.542 (1)0.549 (1)0.17 (1)*.5
C24B0.557 (3)0.615 (1)0.551 (1)0.13 (1)*.5
F25B0.635 (2)0.5758 (9)0.4899 (8)0.151 (8)*.5
F26B0.436 (3)0.667 (1)0.517 (1)0.147 (8)*.5
F27B0.462 (3)0.558 (1)0.589 (1)0.180 (9)*.5
H10.33281.09700.54690.054*
H3−0.07831.09110.70250.071*
H40.08090.99540.77090.070*
H60.36240.90150.78390.058*
H80.76620.90840.61940.058*
H90.60831.01130.55480.060*
H120.80810.85430.77200.055*
H150.26510.70120.89090.067*
H160.45120.78030.98000.060*
H170.69280.85200.91040.059*
H190.51350.73470.64540.075*
H210.93900.60180.55820.111*
H221.14520.66830.64050.112*
H231.03810.76740.72610.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.0456 (2)0.0716 (2)0.0431 (2)−0.0051 (2)0.0067 (2)0.0027 (2)
N10.050 (2)0.044 (2)0.036 (1)0.005 (1)0.008 (2)0.003 (2)
C20.057 (2)0.045 (2)0.042 (2)0.006 (2)0.003 (2)−0.001 (2)
C30.058 (2)0.064 (2)0.047 (2)0.016 (3)0.013 (2)0.008 (2)
C40.059 (2)0.065 (3)0.043 (2)0.012 (2)0.014 (2)0.012 (2)
C50.045 (2)0.045 (2)0.036 (2)0.004 (2)0.001 (2)0.000 (2)
C60.050 (3)0.050 (2)0.038 (2)0.000 (2)0.011 (2)0.009 (2)
C70.039 (2)0.047 (2)0.037 (2)−0.001 (2)0.002 (2)−0.001 (2)
C80.035 (2)0.056 (2)0.050 (2)0.004 (2)0.008 (2)0.003 (2)
C90.051 (2)0.053 (2)0.039 (2)−0.002 (2)0.009 (2)0.009 (2)
C100.046 (2)0.037 (2)0.035 (2)−0.001 (2)0.002 (2)−0.003 (2)
O110.076 (2)0.067 (2)0.050 (2)0.032 (2)0.012 (2)0.016 (1)
C120.037 (2)0.055 (2)0.039 (2)0.000 (2)−0.001 (2)0.005 (2)
N130.035 (2)0.044 (2)0.037 (2)0.000 (1)−0.001 (1)0.003 (1)
N140.051 (2)0.051 (2)0.049 (2)−0.010 (2)0.002 (2)−0.007 (2)
C150.055 (2)0.054 (2)0.052 (2)−0.014 (2)0.005 (2)−0.002 (2)
N160.043 (2)0.064 (2)0.037 (2)0.006 (2)0.003 (2)0.004 (1)
C170.042 (2)0.060 (2)0.039 (2)−0.003 (2)−0.005 (2)−0.005 (2)
C180.045 (2)0.059 (3)0.044 (2)0.017 (2)0.008 (2)0.013 (2)
C190.053 (2)0.073 (3)0.054 (2)0.021 (2)0.001 (2)−0.008 (2)
C200.077 (3)0.078 (3)0.056 (3)0.023 (3)0.008 (3)−0.012 (3)
C210.096 (4)0.094 (3)0.075 (3)0.046 (3)0.024 (3)−0.009 (3)
C220.057 (3)0.111 (4)0.101 (4)0.037 (3)0.024 (3)0.004 (3)
C230.046 (2)0.078 (3)0.078 (3)0.019 (3)0.006 (3)0.008 (3)
C24A0.09 (1)0.08 (1)0.064 (8)0.02 (1)0.00 (1)−0.046 (9)
F25A0.18 (1)0.23 (2)0.070 (6)0.04 (1)−0.004 (6)−0.052 (8)
F26A0.066 (7)0.18 (2)0.17 (1)0.019 (8)0.008 (8)−0.12 (1)
F27A0.20 (2)0.114 (9)0.20 (2)−0.01 (1)−0.05 (2)−0.05 (1)
C24B0.14 (3)0.17 (3)0.09 (1)0.07 (2)0.01 (1)−0.04 (2)
F25B0.136 (8)0.17 (2)0.14 (2)0.01 (1)0.03 (1)−0.11 (1)
F26B0.18 (2)0.15 (1)0.107 (7)0.04 (1)−0.09 (1)−0.044 (7)
F27B0.22 (2)0.14 (1)0.18 (1)−0.06 (1)−0.01 (1)−0.038 (9)
Geometric parameters (Å, º) top
N1—C21.357 (5)N14—C151.303 (5)
N1—C101.379 (4)C15—N161.345 (5)
N1—H10.860C15—H150.930
C2—C31.436 (5)N16—C171.315 (4)
C2—O111.242 (4)N16—H160.860
C3—C41.330 (5)C17—H170.930
C3—H30.930C18—C191.373 (5)
C4—C51.426 (5)C18—C231.379 (6)
C4—H40.930C19—C201.376 (6)
C5—C61.404 (5)C19—H190.930
C5—C101.385 (5)C20—C211.366 (7)
C6—C71.370 (5)C20—C24A1.50 (2)
C6—H60.930C20—C24B1.49 (2)
C7—C81.405 (5)C21—C221.363 (7)
C7—C121.518 (5)C21—H210.930
C8—C91.366 (5)C22—C231.373 (7)
C8—H80.930C22—H220.930
C9—C101.394 (5)C23—H230.930
C9—H90.930C24A—F25A1.34 (2)
C12—N131.479 (4)C24A—F26A1.31 (2)
C12—C181.508 (5)C24A—F27A1.31 (2)
C12—H120.980C24B—F25B1.33 (3)
N13—N141.373 (4)C24B—F26B1.33 (3)
N13—C171.302 (4)C24B—F27B1.31 (3)
C2—N1—C10124.0 (3)N14—C15—H15124.0
C2—N1—H1118.0N16—C15—H15124.0
C10—N1—H1118.0C15—N16—C17106.5 (3)
N1—C2—C3116.1 (3)C15—N16—H16126.8
N1—C2—O11120.5 (3)C17—N16—H16126.8
C3—C2—O11123.4 (3)N13—C17—N16107.6 (3)
C2—C3—C4121.5 (3)N13—C17—H17126.2
C2—C3—H3119.3N16—C17—H17126.2
C4—C3—H3119.3C12—C18—C19121.5 (3)
C3—C4—C5121.1 (4)C12—C18—C23119.7 (3)
C3—C4—H4119.4C19—C18—C23118.7 (4)
C5—C4—H4119.4C18—C19—C20120.9 (4)
C4—C5—C6122.8 (3)C18—C19—H19119.6
C4—C5—C10118.0 (3)C20—C19—H19119.6
C6—C5—C10119.1 (3)C19—C20—C21119.9 (4)
C5—C6—C7121.3 (3)C19—C20—C24A122.8 (7)
C5—C6—H6119.4C19—C20—C24B115.6 (9)
C7—C6—H6119.4C21—C20—C24A117.0 (8)
C6—C7—C8118.4 (3)C21—C20—C24B124.1 (9)
C6—C7—C12123.3 (3)C20—C21—C22119.6 (5)
C8—C7—C12118.2 (3)C20—C21—H21120.2
C7—C8—C9121.3 (3)C22—C21—H21120.2
C7—C8—H8119.4C21—C22—C23120.8 (4)
C9—C8—H8119.4C21—C22—H22119.6
C8—C9—C10119.8 (3)C23—C22—H22119.6
C8—C9—H9120.1C18—C23—C22120.1 (4)
C10—C9—H9120.1C18—C23—H23120.0
N1—C10—C5119.3 (3)C22—C23—H23120.0
N1—C10—C9120.7 (3)C20—C24A—F25A113 (1)
C5—C10—C9120.1 (3)C20—C24A—F26A113 (1)
C7—C12—N13110.1 (3)C20—C24A—F27A111 (1)
C7—C12—C18113.0 (3)F25A—C24A—F26A107 (2)
C7—C12—H12107.0F25A—C24A—F27A109 (2)
N13—C12—C18112.2 (3)F26A—C24A—F27A103 (2)
N13—C12—H12107.0C20—C24B—F25B110 (2)
C18—C12—H12107.0C20—C24B—F26B110 (2)
C12—N13—N14122.4 (3)C20—C24B—F27B118 (2)
C12—N13—C17125.9 (3)F25B—C24B—F26B104 (2)
N14—N13—C17111.1 (3)F25B—C24B—F27B105 (2)
N13—N14—C15102.7 (3)F26B—C24B—F27B109 (2)
N14—C15—N16112.0 (3)
C10—N1—C2—C30.7 (5)N13—C12—C18—C23−107.6 (4)
C10—N1—C2—O11179.8 (3)H12—C12—C18—C19−169.2
H1—N1—C2—C3−179.3H12—C12—C18—C239.6
H1—N1—C2—O11−0.2C12—N13—N14—C15−172.8 (3)
C2—N1—C10—C5−0.6 (5)C17—N13—N14—C15−0.8 (4)
C2—N1—C10—C9178.5 (3)C12—N13—C17—N16173.4 (3)
H1—N1—C10—C5179.4C12—N13—C17—H17−6.6
H1—N1—C10—C9−1.5N14—N13—C17—N161.7 (4)
N1—C2—C3—C40.1 (5)N14—N13—C17—H17−178.4
N1—C2—C3—H3−179.9N13—N14—C15—N16−0.4 (4)
O11—C2—C3—C4−179.1 (4)N13—N14—C15—H15179.6
O11—C2—C3—H30.9N14—C15—N16—C171.4 (4)
C2—C3—C4—C5−0.8 (6)N14—C15—N16—H16−178.6
C2—C3—C4—H4179.2H15—C15—N16—C17−178.6
H3—C3—C4—C5179.2H15—C15—N16—H161.4
H3—C3—C4—H4−0.8C15—N16—C17—N13−1.8 (4)
C3—C4—C5—C6−178.0 (3)C15—N16—C17—H17178.2
C3—C4—C5—C100.9 (5)H16—N16—C17—N13178.2
H4—C4—C5—C62.0H16—N16—C17—H17−1.8
H4—C4—C5—C10−179.1C12—C18—C19—C20179.2 (4)
C4—C5—C6—C7178.6 (3)C12—C18—C19—H19−0.8
C4—C5—C6—H6−1.4C23—C18—C19—C200.4 (6)
C10—C5—C6—C7−0.3 (5)C23—C18—C19—H19−179.6
C10—C5—C6—H6179.7C12—C18—C23—C22−178.9 (4)
C4—C5—C10—N1−0.2 (5)C12—C18—C23—H231.1
C4—C5—C10—C9−179.3 (3)C19—C18—C23—C22−0.1 (6)
C6—C5—C10—N1178.7 (3)C19—C18—C23—H23179.9
C6—C5—C10—C9−0.4 (5)C18—C19—C20—C21−0.4 (7)
C5—C6—C7—C80.3 (5)C18—C19—C20—C24A−174.9 (8)
C5—C6—C7—C12179.7 (3)C18—C19—C20—C24B172.2 (9)
H6—C6—C7—C8−179.7H19—C19—C20—C21179.6
H6—C6—C7—C12−0.3H19—C19—C20—C24A5.1
C6—C7—C8—C90.5 (5)H19—C19—C20—C24B−7.8
C6—C7—C8—H8−179.5C19—C20—C21—C220.1 (7)
C12—C7—C8—C9−178.9 (3)C19—C20—C21—H21−179.9
C12—C7—C8—H81.1C24A—C20—C21—C22174.9 (8)
C6—C7—C12—N137.0 (4)C24A—C20—C21—H21−5.2
C6—C7—C12—C18133.4 (3)C24B—C20—C21—C22−171 (1)
C6—C7—C12—H12−109.0C24B—C20—C21—H218.2
C8—C7—C12—N13−173.6 (3)C19—C20—C24A—F25A122 (1)
C8—C7—C12—C18−47.2 (4)C19—C20—C24A—F26A1 (2)
C8—C7—C12—H1270.4C19—C20—C24A—F27A−114 (1)
C7—C8—C9—C10−1.2 (5)C21—C20—C24A—F25A−51 (2)
C7—C8—C9—H9178.8C21—C20—C24A—F26A−173 (1)
H8—C8—C9—C10178.8C21—C20—C24A—F27A71 (2)
H8—C8—C9—H9−1.2C19—C20—C24B—F25B164 (1)
C8—C9—C10—N1−178.0 (3)C19—C20—C24B—F26B50 (2)
C8—C9—C10—C51.1 (5)C19—C20—C24B—F27B−75 (2)
H9—C9—C10—N12.0C21—C20—C24B—F25B−23 (2)
H9—C9—C10—C5−178.9C21—C20—C24B—F26B−136 (1)
C7—C12—N13—N1474.5 (4)C21—C20—C24B—F27B96 (2)
C7—C12—N13—C17−96.4 (4)C20—C21—C22—C230.2 (8)
C18—C12—N13—N14−52.4 (4)C20—C21—C22—H22−179.8
C18—C12—N13—C17136.8 (3)H21—C21—C22—C23−179.8
H12—C12—N13—N14−169.5H21—C21—C22—H220.2
H12—C12—N13—C1719.6C21—C22—C23—C18−0.2 (7)
C7—C12—C18—C19−51.6 (5)C21—C22—C23—H23179.8
C7—C12—C18—C23127.2 (4)H22—C22—C23—C18179.8
N13—C12—C18—C1973.7 (4)H22—C22—C23—H23−0.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br0.862.463.293 (3)162
N16—H16···O11i0.861.862.642 (4)150
C17—H17···Brii0.932.583.387 (4)145
C15—H15···O11iii0.932.273.173 (5)163
Symmetry codes: (i) −x+1/2, −y+2, z+1/2; (ii) −x+3/2, −y+2, z+1/2; (iii) −x, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC19H14F3N4O+·Br−
Mr451.25
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)7.058 (4), 16.212 (8), 17.029 (9)
V (Å3)1949 (2)
Z4
Radiation typeMo Kα
µ (mm−1)2.15
Crystal size (mm)0.50 × 0.30 × 0.30
Data collection
DiffractometerStoe Stadi-4 four-circle
diffractometer
Absorption correctionψ scan
(EMPIR; Stoe & Cie, 1992)
Tmin, Tmax0.427, 0.525
No. of measured, independent and
observed [I > 2σ(I)] reflections		5505, 3463, 2660
Rint0.029
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.064, 1.04
No. of reflections3463
No. of parameters289
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.21, −0.22
Absolute structureFlack (1983), 1457 Friedel pairs
Absolute structure parameter0.000 (9)

Computer programs: DIF4 (Stoe & Cie, 1992), DIF4, REDU4 (Stoe & Cie, 1992), 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
N1—H1···Br0.862.463.293 (3)162
N16—H16···O11i0.861.862.642 (4)150
C17—H17···Brii0.932.583.387 (4)145
C15—H15···O11iii0.932.273.173 (5)163
Symmetry codes: (i) −x+1/2, −y+2, z+1/2; (ii) −x+3/2, −y+2, z+1/2; (iii) −x, y−1/2, −z+3/2.
 

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