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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Feb 5;67(Pt 3):o579. doi: 10.1107/S1600536811003540

4-Bromo-3-methyl­anilinium perchlorate 18-crown-6 clathrate

Qian Xu a, Min Min Zhao a,*
PMCID: PMC3052115  PMID: 21522341

Abstract

The reaction of 4-bromo-3-methyl­anilinium perchlorate and 18-crown-6 in methanol solution yielded the title compound, C7H9BrN+·ClO4 −·C12H24O6. The protonated 4-bromo-3-methyl­amine unit contains one –NH3 + substituent, resulting in a 1:1 supra­molecular rotator–stator structure, (C7H9Br—NH3 +)(18-crown-6), through three bifurcated N—H⋯(O,O) hydrogen bonds between the ammonium group of the cation and the O atoms of the crown ether mol­ecule.

Related literature

For the structures of similar crown ether clathrates, see: Akutagawa et al. (2002 ▶); Ge & Zhao (2010a ▶,b ▶;); Guo & Zhao (2010 ▶); Zhao (2010 ▶); Zhao & Qu (2010a ▶,b ▶). The title compound was prepared as part of a study of ferroelectric materials. For their properties, see: Fu et al. (2007 ▶); Zhang et al. (2009 ▶); Ye et al. (2009 ▶).graphic file with name e-67-0o579-scheme1.jpg

Experimental

Crystal data

  • C7H9BrN+·ClO4 −·C12H24O6

  • M r = 550.81

  • Monoclinic, Inline graphic

  • a = 11.967 (2) Å

  • b = 13.446 (3) Å

  • c = 15.677 (3) Å

  • β = 94.05 (3)°

  • V = 2516.3 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.79 mm−1

  • T = 296 K

  • 0.40 × 0.30 × 0.20 mm

Data collection

  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.530, T max = 0.699

  • 25007 measured reflections

  • 5665 independent reflections

  • 4005 reflections with I > 2σ(I)

  • R int = 0.066

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060

  • wR(F 2) = 0.157

  • S = 1.09

  • 5665 reflections

  • 289 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.98 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003540/jh2260sup1.cif

e-67-0o579-sup1.cif (22.8KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003540/jh2260Isup2.hkl

e-67-0o579-Isup2.hkl (277.4KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O8 0.89 2.22 2.905 (4) 134
N1—H1A⋯O9 0.89 2.19 2.966 (4) 145
N1—H1B⋯O5 0.89 2.19 2.955 (4) 144
N1—H1B⋯O10 0.89 2.22 2.912 (4) 134
N1—H1E⋯O6 0.89 2.29 2.970 (4) 133
N1—H1E⋯O7 0.89 2.12 2.893 (4) 145
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Acknowledgments

The authors are grateful to the starter fund of Southeast University for financial support to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

There is currently a great deal of interest in crown ethers because of their ability to form non-covalent, H-bonding complexes with ammonium cations both in solid and in solution (Akutagawa et al., 2002; Ge et al., 2010a,b; Guo et al., 2010; Zhao et al., 2010a,b). Not only the size of the crown ether, but also the nature of the ammonium cation (–NH4+, RNH3+, R2NH2+, etc) can influence on the stoichiometry and stability of these host–guest complexes. The host molecules combine with the guest species by intermolecular interaction, and if the host molecule possess some specific sites, it is easy to realise high selectivity in ion or molecular recognitions. 18-Crown-6 have the highest affinity for ammonium cation RNH3+, while most studies of 18-crown-6 and its derivatives invariably showed a 1:1 stoichiometry with RNH3+ cations.

Dielectric permittivity of the title compound is tested to systematically investigate the ferroelectric phase transitions materials (Ye et al., 2009; Zhang et al., 2009). The title compound has no dielectric anomaly with the value of 5 and 8 under 1M Hz in the temperature from 80 to 433 K (the compound m.p.> 453 K), suggesting that the compound should be no distinct phase transition occurred within the measured temperature range.

The title compound is composed of cationic [C7H9NBr(18-Crown-6)]+ and one single anionic [ClO4]- anions (Fig. 1). Supramolecular rotators was assembled between protonated 4-bromo-3-methylanilinium [C7H6Br—NH3]+ and 18-crown-6 by hydrogen-bonding. The ammonium moieties of (–NH3+) cations were interacted with the oxygen atom of crown ethers through six simple N—H···O hydrogen bonding, forming 1:1 supramolecular rotator-stator structures.

The macrocycle adopts a conformation with approximate D3 d symmetry, with all O—C—C—O torsion angles being gauche and alternating in sign, and all C—O—C—C torsion angles being trans. The C—N bonds of [C7H6Br—NH3]+ were almost perpendicular to the mean oxygen planes of crown ethers.

Supramolecular cation structure, [C7H9NBr(18-Crown-6)]+, were introduced as counter cations to [ClO4]- anions. Cl has a flattened tetrahedral coordination by four O2- ions [range of cis-bond angles = 108.4 (2)–110.3 (2) °; dav(Cl—O) = 1.426 (3)–1.457 (3) Å].

The title compound was stabilized by intramolecular N—H···O hydrogen bonds, but no intermolecular hydrogen bond was observed. The intramolecular N—H···O hydrogen bonding length are within the usual range: 2.893 (4) and 2.970 (4) Å.

Experimental

C7H8NBr. HClO4 (2 mmol, 0.57 g) and 18-crown-6 (2 mmol, 0.528 g) were dissolved in 40 ml me thanol solution. The precipitate was filtered out. Two days later, single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of methanol solution at 0°C.

Refinement

All the C—H hydrogen atoms were calculated geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

All the N—H hydrogen atoms were calculated geometrically. The positions of the H atoms of the nitrogen atoms were refined using a riding model with N—H = 0.89 Å and Uiso(H) = 1.5Ueq(N).

Figures

Fig. 1.

Fig. 1.

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The title molecules with the atomic numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C7H9BrN+·ClO4−·C12H24O6 F(000) = 1144
Mr = 550.81 Dx = 1.454 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 20001 reflections
a = 11.967 (2) Å θ = 3.0–27.3°
b = 13.446 (3) Å µ = 1.79 mm−1
c = 15.677 (3) Å T = 296 K
β = 94.05 (3)° Prism, colorless
V = 2516.3 (9) Å3 0.40 × 0.30 × 0.20 mm
Z = 4
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Data collection

Rigaku SCXmini diffractometer 5665 independent reflections
Radiation source: fine-focus sealed tube 4005 reflections with I > 2σ(I)
graphite Rint = 0.066
Detector resolution: 28.5714 pixels mm-1 θmax = 27.3°, θmin = 3.0°
CCD_Profile_fitting scans h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) k = −17→17
Tmin = 0.530, Tmax = 0.699 l = −20→20
25007 measured reflections
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157 H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0769P)2 + 0.8528P] where P = (Fo2 + 2Fc2)/3
5665 reflections (Δ/σ)max = 0.001
289 parameters Δρmax = 0.41 e Å−3
0 restraints Δρmin = −0.98 e Å−3
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Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Br1 0.19928 (4) 1.01458 (3) −0.00712 (3) 0.06334 (18)
O8 0.0452 (2) 0.60635 (19) 0.30049 (15) 0.0495 (6)
N1 0.2459 (2) 0.72782 (19) 0.29922 (16) 0.0367 (6)
H1A 0.1796 0.7195 0.3206 0.055*
H1B 0.2937 0.7545 0.3389 0.055*
H1E 0.2719 0.6692 0.2833 0.055*
O9 0.0542 (2) 0.78578 (18) 0.39854 (15) 0.0499 (6)
C15 0.3203 (3) 0.8828 (2) 0.1107 (2) 0.0370 (7)
C16 0.2147 (3) 0.9217 (2) 0.08602 (19) 0.0398 (7)
O6 0.4462 (2) 0.59829 (19) 0.29366 (17) 0.0551 (7)
O5 0.4715 (2) 0.78411 (19) 0.37212 (16) 0.0518 (6)
O7 0.2319 (2) 0.53548 (19) 0.21645 (17) 0.0554 (7)
O10 0.2751 (2) 0.84908 (18) 0.45312 (16) 0.0506 (6)
C13 0.2336 (3) 0.7946 (2) 0.22444 (19) 0.0332 (7)
C17 0.1196 (3) 0.8976 (3) 0.1282 (2) 0.0453 (8)
H17A 0.0503 0.9242 0.1098 0.054*
C18 0.1292 (3) 0.8336 (2) 0.1982 (2) 0.0415 (8)
H18A 0.0664 0.8171 0.2270 0.050*
C14 0.3275 (3) 0.8187 (2) 0.1809 (2) 0.0398 (7)
H14A 0.3966 0.7914 0.1990 0.048*
C11 0.5624 (3) 0.7135 (3) 0.3751 (3) 0.0545 (10)
H11A 0.5601 0.6721 0.4256 0.065*
H11B 0.6335 0.7484 0.3781 0.065*
C6 −0.0296 (3) 0.7105 (3) 0.4065 (2) 0.0537 (9)
H6A −0.0976 0.7405 0.4250 0.064*
H6B −0.0033 0.6619 0.4490 0.064*
C10 0.4740 (3) 0.8459 (3) 0.4471 (3) 0.0600 (10)
H10A 0.5406 0.8872 0.4499 0.072*
H10B 0.4766 0.8045 0.4979 0.072*
C7 0.0804 (3) 0.8360 (3) 0.4778 (2) 0.0562 (10)
H7A 0.1013 0.7881 0.5224 0.067*
H7B 0.0155 0.8726 0.4944 0.067*
C19 0.4241 (3) 0.9087 (3) 0.0644 (3) 0.0580 (10)
H19A 0.4878 0.8747 0.0911 0.087*
H19B 0.4366 0.9792 0.0673 0.087*
H19C 0.4132 0.8887 0.0056 0.087*
C8 0.1762 (3) 0.9065 (3) 0.4666 (3) 0.0579 (10)
H8A 0.1585 0.9496 0.4180 0.070*
H8B 0.1891 0.9476 0.5172 0.070*
C3 0.1271 (4) 0.4814 (3) 0.2176 (3) 0.0600 (10)
H3A 0.1286 0.4386 0.2675 0.072*
H3B 0.1164 0.4401 0.1670 0.072*
C5 −0.0538 (3) 0.6604 (3) 0.3215 (2) 0.0517 (9)
H5A −0.1164 0.6149 0.3244 0.062*
H5B −0.0733 0.7096 0.2778 0.062*
C4 0.0330 (3) 0.5545 (3) 0.2200 (2) 0.0539 (9)
H4A 0.0356 0.6014 0.1731 0.065*
H4B −0.0383 0.5201 0.2144 0.065*
C9 0.3713 (3) 0.9105 (3) 0.4438 (3) 0.0583 (10)
H9A 0.3780 0.9592 0.4895 0.070*
H9B 0.3633 0.9457 0.3897 0.070*
C12 0.5517 (3) 0.6502 (3) 0.2967 (3) 0.0573 (10)
H12A 0.5554 0.6914 0.2462 0.069*
H12B 0.6128 0.6027 0.2978 0.069*
C1 0.4329 (4) 0.5300 (4) 0.2234 (4) 0.0794 (15)
H1C 0.4969 0.4856 0.2243 0.095*
H1D 0.4290 0.5664 0.1698 0.095*
C2 0.3278 (4) 0.4705 (3) 0.2295 (4) 0.0794 (15)
H2A 0.3239 0.4185 0.1866 0.095*
H2B 0.3280 0.4395 0.2854 0.095*
Cl2 0.75937 (7) 0.70425 (7) 0.09959 (6) 0.0485 (2)
O2 0.7570 (3) 0.6235 (2) 0.15986 (19) 0.0709 (8)
O1 0.6613 (3) 0.7637 (3) 0.1044 (3) 0.0979 (12)
O4 0.7607 (3) 0.6624 (3) 0.01394 (19) 0.0784 (9)
O3 0.8582 (3) 0.7636 (3) 0.1177 (2) 0.0849 (10)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Br1 0.0687 (3) 0.0700 (3) 0.0526 (3) 0.0157 (2) 0.0132 (2) 0.02676 (19)
O8 0.0416 (13) 0.0607 (16) 0.0458 (13) −0.0055 (11) −0.0003 (11) −0.0053 (11)
N1 0.0388 (14) 0.0358 (14) 0.0359 (14) −0.0015 (11) 0.0058 (11) 0.0020 (11)
O9 0.0502 (14) 0.0543 (15) 0.0469 (14) −0.0092 (11) 0.0152 (11) −0.0020 (11)
C15 0.0384 (17) 0.0343 (16) 0.0393 (17) 0.0015 (13) 0.0110 (14) −0.0005 (13)
C16 0.052 (2) 0.0352 (17) 0.0332 (16) 0.0051 (14) 0.0053 (14) 0.0025 (13)
O6 0.0451 (14) 0.0589 (16) 0.0627 (16) 0.0068 (12) 0.0125 (12) −0.0091 (13)
O5 0.0417 (14) 0.0535 (15) 0.0588 (16) 0.0012 (11) −0.0066 (12) 0.0054 (12)
O7 0.0568 (16) 0.0443 (14) 0.0657 (17) 0.0002 (12) 0.0081 (13) −0.0090 (12)
O10 0.0548 (15) 0.0390 (13) 0.0585 (16) −0.0048 (11) 0.0074 (12) −0.0054 (11)
C13 0.0372 (16) 0.0302 (15) 0.0326 (15) −0.0003 (12) 0.0049 (13) 0.0004 (12)
C17 0.0337 (17) 0.053 (2) 0.050 (2) 0.0103 (15) 0.0032 (15) 0.0062 (16)
C18 0.0326 (17) 0.0468 (19) 0.0459 (18) 0.0020 (14) 0.0089 (14) 0.0067 (15)
C14 0.0338 (17) 0.0399 (18) 0.0461 (18) 0.0050 (14) 0.0054 (14) 0.0034 (14)
C11 0.0356 (19) 0.056 (2) 0.072 (3) −0.0006 (16) 0.0029 (18) 0.019 (2)
C6 0.044 (2) 0.064 (2) 0.056 (2) −0.0041 (17) 0.0191 (17) 0.0041 (18)
C10 0.053 (2) 0.050 (2) 0.073 (3) −0.0102 (18) −0.016 (2) −0.007 (2)
C7 0.065 (3) 0.059 (2) 0.047 (2) −0.0005 (19) 0.0175 (18) −0.0075 (17)
C19 0.047 (2) 0.061 (2) 0.068 (3) 0.0070 (18) 0.0247 (19) 0.015 (2)
C8 0.066 (3) 0.051 (2) 0.058 (2) 0.0028 (19) 0.0092 (19) −0.0115 (18)
C3 0.072 (3) 0.046 (2) 0.062 (3) −0.0129 (19) 0.003 (2) −0.0103 (18)
C5 0.0389 (19) 0.057 (2) 0.059 (2) −0.0073 (17) 0.0030 (17) 0.0075 (18)
C4 0.059 (2) 0.058 (2) 0.045 (2) −0.0166 (19) −0.0031 (17) −0.0041 (17)
C9 0.056 (2) 0.045 (2) 0.073 (3) −0.0110 (18) −0.004 (2) −0.0066 (18)
C12 0.0360 (19) 0.073 (3) 0.064 (2) 0.0088 (18) 0.0142 (17) 0.013 (2)
C1 0.065 (3) 0.084 (3) 0.091 (4) 0.021 (2) 0.015 (3) −0.035 (3)
C2 0.080 (3) 0.051 (3) 0.107 (4) 0.008 (2) 0.003 (3) −0.032 (3)
Cl2 0.0381 (4) 0.0543 (5) 0.0526 (5) 0.0011 (4) −0.0005 (4) 0.0077 (4)
O2 0.075 (2) 0.0661 (19) 0.0713 (19) −0.0057 (15) 0.0047 (15) 0.0206 (15)
O1 0.074 (2) 0.105 (3) 0.114 (3) 0.043 (2) 0.002 (2) −0.002 (2)
O4 0.080 (2) 0.101 (3) 0.0551 (18) −0.0078 (19) 0.0068 (15) −0.0074 (16)
O3 0.074 (2) 0.097 (2) 0.081 (2) −0.0366 (19) −0.0162 (17) 0.0177 (18)
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Geometric parameters (Å, °)

Br1—C16 1.921 (3) C6—H6B 0.9700
O8—C4 1.440 (4) C10—C9 1.503 (5)
O8—C5 1.448 (4) C10—H10A 0.9700
N1—C13 1.476 (4) C10—H10B 0.9700
N1—H1A 0.8900 C7—C8 1.507 (5)
N1—H1B 0.8900 C7—H7A 0.9700
N1—H1E 0.8900 C7—H7B 0.9700
O9—C7 1.430 (4) C19—H19A 0.9600
O9—C6 1.437 (4) C19—H19B 0.9600
C15—C14 1.396 (4) C19—H19C 0.9600
C15—C16 1.397 (4) C8—H8A 0.9700
C15—C19 1.523 (4) C8—H8B 0.9700
C16—C17 1.393 (5) C3—C4 1.497 (6)
O6—C1 1.435 (5) C3—H3A 0.9700
O6—C12 1.440 (4) C3—H3B 0.9700
O5—C10 1.437 (5) C5—H5A 0.9700
O5—C11 1.442 (4) C5—H5B 0.9700
O7—C2 1.445 (5) C4—H4A 0.9700
O7—C3 1.451 (5) C4—H4B 0.9700
O10—C9 1.432 (4) C9—H9A 0.9700
O10—C8 1.440 (4) C9—H9B 0.9700
C13—C18 1.390 (4) C12—H12A 0.9700
C13—C14 1.394 (4) C12—H12B 0.9700
C17—C18 1.393 (4) C1—C2 1.498 (7)
C17—H17A 0.9300 C1—H1C 0.9700
C18—H18A 0.9300 C1—H1D 0.9700
C14—H14A 0.9300 C2—H2A 0.9700
C11—C12 1.493 (6) C2—H2B 0.9700
C11—H11A 0.9700 Cl2—O1 1.426 (3)
C11—H11B 0.9700 Cl2—O3 1.439 (3)
C6—C5 1.503 (5) Cl2—O2 1.441 (3)
C6—H6A 0.9700 Cl2—O4 1.457 (3)
C4—O8—C5 114.1 (3) C15—C19—H19C 109.5
C13—N1—H1A 109.5 H19A—C19—H19C 109.5
C13—N1—H1B 109.5 H19B—C19—H19C 109.5
H1A—N1—H1B 109.5 O10—C8—C7 108.7 (3)
C13—N1—H1E 109.5 O10—C8—H8A 110.0
H1A—N1—H1E 109.5 C7—C8—H8A 110.0
H1B—N1—H1E 109.5 O10—C8—H8B 110.0
C7—O9—C6 111.6 (3) C7—C8—H8B 110.0
C14—C15—C16 117.0 (3) H8A—C8—H8B 108.3
C14—C15—C19 120.6 (3) O7—C3—C4 108.9 (3)
C16—C15—C19 122.3 (3) O7—C3—H3A 109.9
C17—C16—C15 122.3 (3) C4—C3—H3A 109.9
C17—C16—Br1 118.3 (2) O7—C3—H3B 109.9
C15—C16—Br1 119.4 (2) C4—C3—H3B 109.9
C1—O6—C12 112.7 (3) H3A—C3—H3B 108.3
C10—O5—C11 112.5 (3) O8—C5—C6 108.5 (3)
C2—O7—C3 112.0 (3) O8—C5—H5A 110.0
C9—O10—C8 112.4 (3) C6—C5—H5A 110.0
C18—C13—C14 120.5 (3) O8—C5—H5B 110.0
C18—C13—N1 120.1 (3) C6—C5—H5B 110.0
C14—C13—N1 119.4 (3) H5A—C5—H5B 108.4
C18—C17—C16 119.5 (3) O8—C4—C3 108.0 (3)
C18—C17—H17A 120.2 O8—C4—H4A 110.1
C16—C17—H17A 120.2 C3—C4—H4A 110.1
C13—C18—C17 119.2 (3) O8—C4—H4B 110.1
C13—C18—H18A 120.4 C3—C4—H4B 110.1
C17—C18—H18A 120.4 H4A—C4—H4B 108.4
C13—C14—C15 121.4 (3) O10—C9—C10 108.9 (3)
C13—C14—H14A 119.3 O10—C9—H9A 109.9
C15—C14—H14A 119.3 C10—C9—H9A 109.9
O5—C11—C12 109.2 (3) O10—C9—H9B 109.9
O5—C11—H11A 109.8 C10—C9—H9B 109.9
C12—C11—H11A 109.8 H9A—C9—H9B 108.3
O5—C11—H11B 109.8 O6—C12—C11 109.1 (3)
C12—C11—H11B 109.8 O6—C12—H12A 109.9
H11A—C11—H11B 108.3 C11—C12—H12A 109.9
O9—C6—C5 109.3 (3) O6—C12—H12B 109.9
O9—C6—H6A 109.8 C11—C12—H12B 109.9
C5—C6—H6A 109.8 H12A—C12—H12B 108.3
O9—C6—H6B 109.8 O6—C1—C2 109.9 (4)
C5—C6—H6B 109.8 O6—C1—H1C 109.7
H6A—C6—H6B 108.3 C2—C1—H1C 109.7
O5—C10—C9 109.7 (3) O6—C1—H1D 109.7
O5—C10—H10A 109.7 C2—C1—H1D 109.7
C9—C10—H10A 109.7 H1C—C1—H1D 108.2
O5—C10—H10B 109.7 O7—C2—C1 109.3 (4)
C9—C10—H10B 109.7 O7—C2—H2A 109.8
H10A—C10—H10B 108.2 C1—C2—H2A 109.8
O9—C7—C8 108.5 (3) O7—C2—H2B 109.8
O9—C7—H7A 110.0 C1—C2—H2B 109.8
C8—C7—H7A 110.0 H2A—C2—H2B 108.3
O9—C7—H7B 110.0 O1—Cl2—O3 110.3 (2)
C8—C7—H7B 110.0 O1—Cl2—O2 109.5 (2)
H7A—C7—H7B 108.4 O3—Cl2—O2 110.04 (19)
C15—C19—H19A 109.5 O1—Cl2—O4 109.1 (2)
C15—C19—H19B 109.5 O3—Cl2—O4 109.5 (2)
H19A—C19—H19B 109.5 O2—Cl2—O4 108.4 (2)
C14—C15—C16—C17 −0.6 (5) C6—O9—C7—C8 174.6 (3)
C19—C15—C16—C17 179.8 (3) C9—O10—C8—C7 −178.6 (3)
C14—C15—C16—Br1 177.5 (2) O9—C7—C8—O10 −67.0 (4)
C19—C15—C16—Br1 −2.1 (4) C2—O7—C3—C4 169.7 (4)
C15—C16—C17—C18 0.7 (5) C4—O8—C5—C6 180.0 (3)
Br1—C16—C17—C18 −177.4 (3) O9—C6—C5—O8 66.3 (4)
C14—C13—C18—C17 −0.5 (5) C5—O8—C4—C3 −164.9 (3)
N1—C13—C18—C17 179.1 (3) O7—C3—C4—O8 −66.0 (4)
C16—C17—C18—C13 −0.2 (5) C8—O10—C9—C10 169.2 (3)
C18—C13—C14—C15 0.6 (5) O5—C10—C9—O10 68.3 (4)
N1—C13—C14—C15 −178.9 (3) C1—O6—C12—C11 −175.7 (4)
C16—C15—C14—C13 −0.1 (5) O5—C11—C12—O6 −60.0 (4)
C19—C15—C14—C13 179.6 (3) C12—O6—C1—C2 173.7 (4)
C10—O5—C11—C12 178.1 (3) C3—O7—C2—C1 177.2 (4)
C7—O9—C6—C5 180.0 (3) O6—C1—C2—O7 67.1 (5)
C11—O5—C10—C9 −174.4 (3)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
N1—H1B···O5 0.89 2.19 2.955 (4) 144
N1—H1E···O6 0.89 2.29 2.970 (4) 133
N1—H1E···O7 0.89 2.12 2.893 (4) 145
N1—H1A···O8 0.89 2.22 2.905 (4) 134
N1—H1A···O9 0.89 2.19 2.966 (4) 145
N1—H1B···O10 0.89 2.22 2.912 (4) 134
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2260).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003540/jh2260sup1.cif

e-67-0o579-sup1.cif (22.8KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003540/jh2260Isup2.hkl

e-67-0o579-Isup2.hkl (277.4KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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