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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1570–o1571.
Published online 2008 July 23. doi:  10.1107/S160053680802254X
PMCID: PMC2962191

4-(4-Bromo­benzyl­ideneamino)-3-{1-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-1-(mor­phol­ino­meth­yl)-1H-1,2,4-triazole-5(4H)-thione

Abstract

There are two mol­ecules (A and B) in the asymmetric unit of the title compound, C26H32BrN5OS, with almost identical geometry. The morpholine ring adopts the usual chair conformation in both mol­ecules. The triazole ring forms dihedral angles of 4.84 (6) and 74.19 (6)°, respectively, with the bromo­phenyl and isobutylbenzene rings in mol­ecule A, and angles of 16.68 (7) and 87.29 (6)°, respectively, in mol­ecule B. Intra­molecular C—H(...)S hydrogen bonds generate S(5) and S(6) ring motifs in both independent mol­ecules. The crystal structure is stabilized by C—H(...)N, C—H(...)Br and C—H(...)O hydrogen-bonding inter­actions, together with C—H(...)π inter­actions.

Related literature

For general background, see: Raman et al. (2004 [triangle]); Tramontini et al. (1988 [triangle]); Tramontini & Angliolini (1990 [triangle]); Lopes et al. (2004 [triangle]); Joshi et al. (2004 [triangle]); Ferlin et al. (2002 [triangle]); Holla et al. (2003 [triangle]); Malinka et al. (2005 [triangle]); Karthikeyan et al. (2006 [triangle]); Palaska et al. (2002 [triangle]). For related structures, see: Fun, Jebas, Razak et al. (2008 [triangle]); Fun, Jebas, Sujith et al. (2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For ring puckering analysis, see: Cremer & Pople (1975 [triangle]). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1570-scheme1.jpg

Experimental

Crystal data

  • C26H32BrN5OS
  • M r = 542.54
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1570-efi1.jpg
  • a = 10.1381 (1) Å
  • b = 17.0356 (2) Å
  • c = 17.2077 (2) Å
  • α = 64.168 (1)°
  • β = 79.773 (1)°
  • γ = 78.816 (1)°
  • V = 2609.55 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.68 mm−1
  • T = 100.0 (1) K
  • 0.45 × 0.34 × 0.26 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.522, T max = 0.639
  • 89536 measured reflections
  • 18804 independent reflections
  • 13217 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.097
  • S = 1.02
  • 18804 reflections
  • 619 parameters
  • H-atom parameters constrained
  • Δρmax = 1.33 e Å−3
  • Δρmin = −0.84 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802254X/ci2634sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802254X/ci2634Isup2.hkl

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

Acknowledgments

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for a postdoctoral research fellowship. BK and AM acknowledge the Kerala State Council for Science, Technology and Environment, Thiruvananthapuram, for financial assistance.

supplementary crystallographic information

Comment

Mannich reaction is a three-component condensation reaction involving active hydrogen containing compound, formaldehyde and a secondary amine (Raman et al., 2004). The amino alkylation of aromatic substrates by Mannich reaction is of considerable importance for the synthesis and modification of biologically active compounds (Tramontini & Angliolini, 1990). Mannich bases have been reported as potential biological agents. They find applications as antitubercular (Joshi et al., 2004), antimalarial (Lopes et al., 2004), vasorelaxing (Ferlin et al., 2002), anticancer (Holla et al., 2003), and analgesic drugs (Malinka et al., 2005). They are also used in polymer industry as paints and surface active agents (Tramontini et al., 1988). Some Mannich bases are reported to exhibit activity in vitro against murine P388 lymphocytic leukemia cells (Karthikeyan et al., 2006). Similarly, ibuprofen belongs to the class of Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) with antipyretic, anti-inflammatory and analgesic properties (Palaska et al., 2002). Previously, we have reported crystal structures of triazole derivatives containing a ibuprofen moiety (Fun, Jebas, Razak et al., 2008; Fun, Jebas, Sujith et al., 2008). In continuation of our work, we report here the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (A and B) with almost similar geometries. The bond lengths and angles are found to have normal values (Allen et al., 1987). The triazole rings in both molecules are planar with maximum deviations of 0.013 (2) Å and 0.023 (2) Å, respectively, for atoms C8A and N2B. The morpholine ring in both molecules adopt the usual chair conformation with puckering parameters Q = 0.578 (2) Å, θ = 176.6 (2)° and [var phi]=152 (3)° in molecule A, and Q = 0.571 (2) Å,θ = 2.0 (2)° and [var phi] = 70 (5)° in molecule B (Cremer & Pople, 1975). The N2A/C8A/N3A/N4A/C14A plane forms dihedral angles of 4.84 (6)° and 74.19 (6)°, respectively, with the C1A–C6A and C16A–C21A plane. The dihedral angle formed by the N2B/C8B/N3B/N4B/C14B plane with the C1B–C6B and C16B–C21B planes are 16.68 (7)° and 87.29 (6)°, respectively. Intramolecular C—H···S hydrogen bonds generate S(5) and S(6) ring motifs in both molecules (Bernstein et al., 1995).

The crystal packing is stabilized by intermolecular C—H···N, C—H···Br and C—H···O hydrogen bonding interactions together with C—H···π interactions.

Experimental

The title Mannich-base compound was obtained by the aminomethylation of its corresponding Schiff base, which was in turn obtained by refluxing a mixture of 4-amino-5-[1-(4-isobutylphenyl)ethyl]-4H-1,2,4-triazole-3-thiol (0.01 mol), 4-bromo-benzaldehyde (0.01 mol) in ethanol (50 ml) and 3 drops of concentrated H2SO4 for 3 h. A mixture of the above Schiff base (0.01 mol), formaldehyde (40%, 1 ml) and morpholine (0.01 mol) in ethanol (50 ml) was stirred at room temperature for 20 h. The solid product obtained was collected by filtration, washed with ethanol and dried. It was then recrystallized using ethanol. Single crystals suitable for X-ray analysis were obtained from acetone-N,N-dimethylformamide (DMF) (1:3) solution by slow evaporation (yield 85%; m.p. 383 K). Analysis for C26H32N5BrOS found (calculated%): C 57.55 (57.564), H 5.81 (5.904), N 12.82 (12.915), S 5.82 (5.904).

Refinement

H atoms were positioned geometrically (C-H = 0.93-0.98 Å) and refined using a riding model, with Uiso(H) = 1.2-1.5 Ueq(C). A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C26H32BrN5OSZ = 4
Mr = 542.54F000 = 1128
Triclinic, P1Dx = 1.381 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.1381 (1) ÅCell parameters from 9909 reflections
b = 17.0356 (2) Åθ = 2.2–29.6º
c = 17.2077 (2) ŵ = 1.68 mm1
α = 64.168 (1)ºT = 100.0 (1) K
β = 79.773 (1)ºBlock, colourless
γ = 78.816 (1)º0.45 × 0.34 × 0.26 mm
V = 2609.55 (6) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer18804 independent reflections
Radiation source: fine-focus sealed tube13217 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.044
T = 100.0(1) Kθmax = 32.5º
[var phi] and ω scansθmin = 1.3º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −15→14
Tmin = 0.523, Tmax = 0.639k = −25→25
89536 measured reflectionsl = −26→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.097  w = 1/[σ2(Fo2) + (0.038P)2 + 1.3091P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
18804 reflectionsΔρmax = 1.33 e Å3
619 parametersΔρmin = −0.84 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br1A1.463972 (19)−0.136890 (12)−0.024526 (12)0.02730 (5)
S1A0.72929 (5)0.25031 (3)−0.21857 (3)0.02396 (9)
O1A0.19942 (14)0.30933 (10)−0.05409 (9)0.0338 (3)
N1A0.94677 (15)0.20300 (9)−0.06764 (9)0.0216 (3)
N2A0.83105 (14)0.26411 (9)−0.08571 (9)0.0195 (3)
N3A0.65694 (15)0.35672 (9)−0.13441 (9)0.0201 (3)
N4A0.69613 (15)0.37728 (9)−0.07311 (9)0.0217 (3)
N5A0.41603 (15)0.40103 (9)−0.15946 (9)0.0220 (3)
C1A1.18024 (19)0.07350 (12)−0.02429 (11)0.0256 (4)
H1AA1.16510.11220.00230.031*
C2A1.29078 (19)0.00937 (13)−0.00761 (11)0.0266 (4)
H2AA1.34980.00410.03060.032*
C3A1.31323 (18)−0.04743 (11)−0.04847 (11)0.0216 (3)
C4A1.22709 (19)−0.04131 (11)−0.10530 (11)0.0231 (3)
H4AA1.2435−0.0796−0.13240.028*
C5A1.11568 (18)0.02303 (11)−0.12113 (11)0.0235 (3)
H5AA1.05670.0277−0.15910.028*
C6A1.09067 (18)0.08075 (11)−0.08100 (11)0.0210 (3)
C7A0.96930 (18)0.14595 (11)−0.09930 (11)0.0231 (3)
H7AA0.90880.1457−0.13400.028*
C8A0.73866 (17)0.28902 (11)−0.14594 (10)0.0196 (3)
C9A0.55336 (18)0.41834 (11)−0.18951 (11)0.0231 (3)
H9AA0.55920.4770−0.19580.028*
H9AB0.57490.4184−0.24680.028*
C10A0.38410 (18)0.32459 (11)−0.16766 (11)0.0229 (3)
H10A0.43800.2717−0.13140.028*
H10B0.40620.3317−0.22740.028*
C11A0.23609 (19)0.31572 (13)−0.14053 (12)0.0281 (4)
H11A0.18260.3664−0.18010.034*
H11B0.21680.2636−0.14360.034*
C12A0.2238 (2)0.38716 (15)−0.05031 (14)0.0332 (4)
H12A0.19420.38450.00750.040*
H12B0.17230.4380−0.09110.040*
C13A0.37267 (19)0.39652 (13)−0.07209 (12)0.0268 (4)
H13A0.38860.4495−0.06930.032*
H13B0.42420.3466−0.03040.032*
C14A0.80121 (18)0.32077 (11)−0.04479 (11)0.0207 (3)
C15A0.88283 (18)0.31567 (11)0.02201 (11)0.0221 (3)
H15A0.97830.30220.00340.027*
C16A0.84828 (17)0.24255 (11)0.11050 (11)0.0210 (3)
C17A0.94838 (18)0.17541 (13)0.15147 (12)0.0248 (4)
H17A1.03560.17390.12350.030*
C18A0.91887 (19)0.11064 (13)0.23385 (12)0.0263 (4)
H18A0.98710.06630.26020.032*
C19A0.79030 (19)0.11052 (12)0.27771 (11)0.0240 (3)
C20A0.68960 (18)0.17745 (12)0.23622 (11)0.0235 (3)
H20A0.60240.17880.26420.028*
C21A0.71812 (18)0.24208 (12)0.15355 (12)0.0231 (3)
H21A0.64940.28560.12660.028*
C22A0.7604 (2)0.04019 (13)0.36753 (12)0.0316 (4)
H22A0.7927−0.01690.36670.038*
H22B0.66320.04370.38230.038*
C23A0.8239 (2)0.04639 (17)0.43828 (13)0.0390 (5)
H23A0.92210.04180.42300.047*
C24A0.7948 (3)−0.0314 (2)0.52512 (14)0.0553 (7)
H24A0.8314−0.02580.56990.083*
H24B0.8358−0.08540.52090.083*
H24C0.6989−0.03190.53890.083*
C25A0.7781 (3)0.13307 (19)0.44434 (17)0.0565 (7)
H25A0.80020.18010.38930.085*
H25B0.82260.13530.48800.085*
H25C0.68200.13920.45960.085*
C26A0.8647 (2)0.40454 (12)0.02743 (13)0.0291 (4)
H26A0.89200.4488−0.02830.044*
H26B0.91920.40060.06960.044*
H26C0.77140.42000.04440.044*
Br1B0.48478 (3)0.645886 (13)0.647264 (13)0.03762 (6)
S1B0.08036 (5)0.55979 (3)0.28269 (3)0.02256 (9)
O1B0.35396 (15)0.25009 (11)0.22342 (11)0.0440 (4)
N1B0.13059 (14)0.44610 (9)0.49490 (9)0.0176 (3)
N2B0.07466 (14)0.41862 (9)0.44400 (8)0.0166 (3)
N3B0.00212 (14)0.39715 (9)0.34664 (8)0.0180 (3)
N4B−0.01975 (14)0.32382 (9)0.42336 (9)0.0190 (3)
N5B0.09910 (15)0.35433 (10)0.22751 (9)0.0219 (3)
C1B0.36569 (18)0.59648 (11)0.45716 (11)0.0233 (3)
H1BA0.37850.61860.39690.028*
C2B0.42654 (19)0.63059 (11)0.49939 (11)0.0256 (4)
H2BA0.48020.67530.46810.031*
C3B0.40603 (18)0.59695 (11)0.58892 (11)0.0227 (3)
C4B0.32932 (17)0.52864 (11)0.63734 (11)0.0212 (3)
H4BA0.31850.50600.69760.025*
C5B0.26936 (17)0.49485 (11)0.59445 (10)0.0192 (3)
H5BA0.21810.44890.62610.023*
C6B0.28537 (17)0.52939 (11)0.50386 (10)0.0183 (3)
C7B0.22076 (17)0.49746 (11)0.45565 (11)0.0200 (3)
H7BA0.24530.51450.39640.024*
C8B0.05586 (16)0.45842 (11)0.35662 (10)0.0178 (3)
C9B−0.01500 (17)0.39801 (11)0.26330 (10)0.0206 (3)
H9BA−0.09410.37010.27100.025*
H9BB−0.03230.45870.22170.025*
C10B0.1158 (2)0.25835 (12)0.27558 (13)0.0304 (4)
H10C0.03300.23590.27910.036*
H10D0.13540.24240.33420.036*
C11B0.2306 (2)0.21881 (15)0.22926 (16)0.0406 (5)
H11C0.24140.15520.26030.049*
H11D0.20920.23370.17130.049*
C12B0.3396 (2)0.34296 (16)0.17616 (14)0.0368 (5)
H12C0.32200.35800.11740.044*
H12D0.42350.36410.17290.044*
C13B0.22578 (18)0.38805 (13)0.21804 (12)0.0258 (4)
H13C0.24720.37800.27470.031*
H13D0.21570.45100.18260.031*
C14B0.02267 (16)0.33944 (10)0.48161 (10)0.0172 (3)
C15B0.01969 (17)0.28116 (10)0.57663 (10)0.0182 (3)
H15B−0.02410.31660.60850.022*
C16B0.16129 (17)0.24513 (10)0.60310 (10)0.0175 (3)
C17B0.26067 (18)0.21508 (11)0.55173 (11)0.0213 (3)
H17B0.24060.21850.49960.026*
C18B0.38945 (18)0.18011 (11)0.57731 (11)0.0224 (3)
H18B0.45430.16040.54190.027*
C19B0.42331 (17)0.17395 (10)0.65474 (10)0.0198 (3)
C20B0.32294 (19)0.20293 (11)0.70662 (11)0.0234 (3)
H20B0.34260.19860.75920.028*
C21B0.19414 (19)0.23818 (11)0.68119 (11)0.0231 (3)
H21B0.12900.25740.71680.028*
C22B0.56389 (17)0.13790 (11)0.68160 (11)0.0220 (3)
H22C0.59430.17790.69900.026*
H22D0.62420.13590.63180.026*
C23B0.57477 (17)0.04546 (11)0.75647 (11)0.0195 (3)
H23B0.51920.04900.80790.023*
C24B0.52154 (19)−0.01900 (11)0.73412 (12)0.0254 (4)
H24D0.5318−0.07650.78080.038*
H24E0.5716−0.02080.68190.038*
H24F0.4276−0.00030.72550.038*
C25B0.72130 (19)0.01507 (12)0.77739 (12)0.0267 (4)
H25D0.7277−0.04230.82460.040*
H25E0.75050.05580.79340.040*
H25F0.77780.01260.72720.040*
C26B−0.06443 (18)0.20662 (11)0.60044 (11)0.0236 (3)
H26D−0.15380.23120.58350.035*
H26E−0.06980.17170.66200.035*
H26F−0.02240.17030.57080.035*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br1A0.02633 (10)0.02249 (9)0.02637 (9)0.00006 (7)−0.00519 (7)−0.00446 (7)
S1A0.0275 (2)0.0264 (2)0.0216 (2)−0.00191 (17)−0.00418 (16)−0.01344 (17)
O1A0.0275 (7)0.0451 (8)0.0330 (7)−0.0110 (6)0.0043 (6)−0.0203 (6)
N1A0.0193 (7)0.0218 (7)0.0243 (7)−0.0027 (5)−0.0016 (5)−0.0103 (6)
N2A0.0193 (7)0.0206 (7)0.0214 (7)−0.0046 (5)−0.0002 (5)−0.0113 (5)
N3A0.0212 (7)0.0204 (7)0.0199 (6)−0.0037 (5)−0.0009 (5)−0.0095 (5)
N4A0.0232 (7)0.0220 (7)0.0227 (7)−0.0058 (6)0.0005 (5)−0.0118 (6)
N5A0.0237 (8)0.0210 (7)0.0206 (7)−0.0010 (6)−0.0028 (5)−0.0085 (6)
C1A0.0271 (9)0.0290 (9)0.0259 (9)−0.0028 (7)−0.0024 (7)−0.0167 (7)
C2A0.0256 (9)0.0331 (10)0.0229 (8)−0.0054 (7)−0.0045 (7)−0.0119 (7)
C3A0.0225 (8)0.0184 (8)0.0200 (8)−0.0031 (6)−0.0016 (6)−0.0043 (6)
C4A0.0269 (9)0.0192 (8)0.0253 (8)−0.0028 (7)−0.0042 (7)−0.0106 (7)
C5A0.0246 (9)0.0239 (8)0.0257 (8)−0.0029 (7)−0.0062 (7)−0.0125 (7)
C6A0.0217 (8)0.0195 (8)0.0213 (8)−0.0047 (6)−0.0010 (6)−0.0078 (6)
C7A0.0227 (9)0.0235 (8)0.0257 (8)−0.0050 (7)−0.0029 (6)−0.0118 (7)
C8A0.0211 (8)0.0194 (8)0.0165 (7)−0.0063 (6)0.0006 (6)−0.0054 (6)
C9A0.0257 (9)0.0179 (8)0.0215 (8)−0.0029 (7)−0.0022 (6)−0.0046 (6)
C10A0.0240 (9)0.0213 (8)0.0219 (8)−0.0004 (7)−0.0042 (6)−0.0078 (7)
C11A0.0242 (9)0.0336 (10)0.0290 (9)−0.0027 (7)−0.0035 (7)−0.0155 (8)
C12A0.0237 (10)0.0465 (12)0.0350 (10)0.0008 (8)−0.0013 (8)−0.0248 (9)
C13A0.0241 (9)0.0321 (10)0.0273 (9)0.0002 (7)−0.0031 (7)−0.0167 (8)
C14A0.0224 (8)0.0197 (8)0.0222 (8)−0.0066 (6)0.0019 (6)−0.0109 (6)
C15A0.0184 (8)0.0259 (9)0.0276 (8)−0.0038 (6)−0.0013 (6)−0.0162 (7)
C16A0.0192 (8)0.0252 (8)0.0257 (8)−0.0033 (6)−0.0025 (6)−0.0168 (7)
C17A0.0154 (8)0.0361 (10)0.0315 (9)0.0002 (7)−0.0041 (7)−0.0228 (8)
C18A0.0234 (9)0.0312 (10)0.0300 (9)0.0048 (7)−0.0114 (7)−0.0181 (8)
C19A0.0266 (9)0.0266 (9)0.0248 (8)−0.0023 (7)−0.0067 (7)−0.0153 (7)
C20A0.0187 (8)0.0290 (9)0.0284 (9)−0.0037 (7)−0.0003 (6)−0.0174 (7)
C21A0.0189 (8)0.0238 (8)0.0293 (9)0.0015 (6)−0.0042 (6)−0.0147 (7)
C22A0.0373 (11)0.0333 (10)0.0267 (9)−0.0062 (8)−0.0083 (8)−0.0123 (8)
C23A0.0300 (11)0.0637 (15)0.0280 (10)−0.0085 (10)−0.0037 (8)−0.0222 (10)
C24A0.0545 (16)0.080 (2)0.0273 (11)−0.0111 (14)−0.0072 (10)−0.0161 (12)
C25A0.0701 (19)0.0764 (19)0.0456 (14)−0.0289 (15)0.0060 (12)−0.0427 (14)
C26A0.0287 (10)0.0284 (9)0.0376 (10)−0.0061 (8)−0.0023 (8)−0.0198 (8)
Br1B0.06026 (15)0.02600 (10)0.03119 (10)−0.01396 (9)−0.02188 (9)−0.00635 (8)
S1B0.0235 (2)0.01844 (19)0.02141 (19)−0.00316 (16)−0.00178 (15)−0.00441 (15)
O1B0.0279 (8)0.0540 (10)0.0624 (10)0.0112 (7)−0.0086 (7)−0.0409 (9)
N1B0.0166 (7)0.0163 (6)0.0215 (6)0.0002 (5)−0.0045 (5)−0.0092 (5)
N2B0.0168 (7)0.0155 (6)0.0179 (6)−0.0016 (5)−0.0018 (5)−0.0074 (5)
N3B0.0181 (7)0.0175 (6)0.0179 (6)−0.0006 (5)−0.0027 (5)−0.0072 (5)
N4B0.0183 (7)0.0177 (6)0.0205 (6)−0.0011 (5)−0.0024 (5)−0.0080 (5)
N5B0.0194 (7)0.0267 (7)0.0236 (7)−0.0007 (6)−0.0032 (5)−0.0146 (6)
C1B0.0248 (9)0.0233 (8)0.0197 (8)−0.0062 (7)−0.0030 (6)−0.0054 (7)
C2B0.0301 (10)0.0198 (8)0.0249 (8)−0.0090 (7)−0.0077 (7)−0.0033 (7)
C3B0.0256 (9)0.0190 (8)0.0252 (8)−0.0015 (6)−0.0104 (7)−0.0084 (7)
C4B0.0212 (8)0.0213 (8)0.0195 (7)0.0000 (6)−0.0047 (6)−0.0073 (6)
C5B0.0178 (8)0.0177 (7)0.0201 (7)−0.0008 (6)−0.0018 (6)−0.0067 (6)
C6B0.0172 (8)0.0178 (7)0.0197 (7)−0.0008 (6)−0.0026 (6)−0.0079 (6)
C7B0.0187 (8)0.0229 (8)0.0199 (7)−0.0025 (6)−0.0010 (6)−0.0109 (6)
C8B0.0135 (7)0.0193 (7)0.0197 (7)0.0011 (6)−0.0014 (5)−0.0087 (6)
C9B0.0178 (8)0.0261 (8)0.0200 (7)0.0006 (6)−0.0062 (6)−0.0113 (7)
C10B0.0319 (10)0.0268 (9)0.0360 (10)0.0005 (8)−0.0028 (8)−0.0184 (8)
C11B0.0349 (12)0.0411 (12)0.0560 (14)0.0033 (9)−0.0026 (10)−0.0337 (11)
C12B0.0234 (10)0.0574 (14)0.0424 (11)−0.0027 (9)0.0007 (8)−0.0352 (11)
C13B0.0202 (9)0.0329 (10)0.0279 (9)−0.0026 (7)−0.0010 (7)−0.0169 (8)
C14B0.0148 (7)0.0152 (7)0.0209 (7)0.0004 (6)−0.0008 (6)−0.0082 (6)
C15B0.0177 (8)0.0170 (7)0.0187 (7)−0.0021 (6)0.0002 (6)−0.0072 (6)
C16B0.0192 (8)0.0132 (7)0.0185 (7)−0.0023 (6)−0.0020 (6)−0.0051 (6)
C17B0.0213 (8)0.0234 (8)0.0200 (8)−0.0001 (6)−0.0030 (6)−0.0105 (6)
C18B0.0186 (8)0.0252 (9)0.0221 (8)−0.0008 (6)0.0006 (6)−0.0105 (7)
C19B0.0215 (8)0.0147 (7)0.0209 (7)−0.0050 (6)−0.0029 (6)−0.0039 (6)
C20B0.0291 (9)0.0222 (8)0.0205 (8)0.0006 (7)−0.0071 (7)−0.0103 (7)
C21B0.0267 (9)0.0228 (8)0.0194 (8)0.0005 (7)−0.0009 (6)−0.0106 (7)
C22B0.0196 (8)0.0206 (8)0.0244 (8)−0.0048 (6)−0.0042 (6)−0.0065 (7)
C23B0.0172 (8)0.0201 (8)0.0205 (7)−0.0007 (6)−0.0036 (6)−0.0080 (6)
C24B0.0262 (9)0.0206 (8)0.0294 (9)−0.0028 (7)−0.0059 (7)−0.0095 (7)
C25B0.0225 (9)0.0279 (9)0.0289 (9)0.0011 (7)−0.0076 (7)−0.0110 (7)
C26B0.0227 (9)0.0223 (8)0.0248 (8)−0.0063 (7)−0.0001 (6)−0.0083 (7)

Geometric parameters (Å, °)

Br1A—C3A1.8975 (18)Br1B—C3B1.9007 (17)
S1A—C8A1.6707 (17)S1B—C8B1.6740 (16)
O1A—C12A1.425 (3)O1B—C12B1.420 (3)
O1A—C11A1.429 (2)O1B—C11B1.423 (3)
N1A—C7A1.275 (2)N1B—C7B1.278 (2)
N1A—N2A1.389 (2)N1B—N2B1.3946 (18)
N2A—C14A1.387 (2)N2B—C14B1.382 (2)
N2A—C8A1.392 (2)N2B—C8B1.386 (2)
N3A—C8A1.351 (2)N3B—C8B1.351 (2)
N3A—N4A1.3850 (19)N3B—N4B1.3853 (18)
N3A—C9A1.470 (2)N3B—C9B1.468 (2)
N4A—C14A1.295 (2)N4B—C14B1.300 (2)
N5A—C9A1.436 (2)N5B—C9B1.444 (2)
N5A—C13A1.462 (2)N5B—C13B1.462 (2)
N5A—C10A1.470 (2)N5B—C10B1.466 (2)
C1A—C2A1.378 (3)C1B—C2B1.383 (2)
C1A—C6A1.399 (2)C1B—C6B1.394 (2)
C1A—H1AA0.93C1B—H1BA0.93
C2A—C3A1.390 (3)C2B—C3B1.381 (2)
C2A—H2AA0.93C2B—H2BA0.93
C3A—C4A1.382 (2)C3B—C4B1.389 (2)
C4A—C5A1.386 (3)C4B—C5B1.382 (2)
C4A—H4AA0.93C4B—H4BA0.93
C5A—C6A1.393 (2)C5B—C6B1.397 (2)
C5A—H5AA0.93C5B—H5BA0.93
C6A—C7A1.466 (2)C6B—C7B1.462 (2)
C7A—H7AA0.93C7B—H7BA0.93
C9A—H9AA0.97C9B—H9BA0.97
C9A—H9AB0.97C9B—H9BB0.97
C10A—C11A1.507 (3)C10B—C11B1.509 (3)
C10A—H10A0.97C10B—H10C0.97
C10A—H10B0.97C10B—H10D0.97
C11A—H11A0.97C11B—H11C0.97
C11A—H11B0.97C11B—H11D0.97
C12A—C13A1.512 (3)C12B—C13B1.512 (3)
C12A—H12A0.97C12B—H12C0.97
C12A—H12B0.97C12B—H12D0.97
C13A—H13A0.97C13B—H13C0.97
C13A—H13B0.97C13B—H13D0.97
C14A—C15A1.495 (2)C14B—C15B1.496 (2)
C15A—C16A1.523 (2)C15B—C16B1.514 (2)
C15A—C26A1.531 (2)C15B—C26B1.533 (2)
C15A—H15A0.98C15B—H15B0.98
C16A—C17A1.391 (2)C16B—C21B1.391 (2)
C16A—C21A1.394 (2)C16B—C17B1.392 (2)
C17A—C18A1.390 (3)C17B—C18B1.388 (2)
C17A—H17A0.93C17B—H17B0.93
C18A—C19A1.385 (3)C18B—C19B1.390 (2)
C18A—H18A0.93C18B—H18B0.93
C19A—C20A1.396 (3)C19B—C20B1.394 (2)
C19A—C22A1.509 (3)C19B—C22B1.506 (2)
C20A—C21A1.390 (3)C20B—C21B1.388 (3)
C20A—H20A0.93C20B—H20B0.93
C21A—H21A0.93C21B—H21B0.93
C22A—C23A1.525 (3)C22B—C23B1.538 (2)
C22A—H22A0.97C22B—H22C0.97
C22A—H22B0.97C22B—H22D0.97
C23A—C25A1.503 (4)C23B—C24B1.522 (2)
C23A—C24A1.532 (3)C23B—C25B1.528 (2)
C23A—H23A0.98C23B—H23B0.98
C24A—H24A0.96C24B—H24D0.96
C24A—H24B0.96C24B—H24E0.96
C24A—H24C0.96C24B—H24F0.96
C25A—H25A0.96C25B—H25D0.96
C25A—H25B0.96C25B—H25E0.96
C25A—H25C0.96C25B—H25F0.96
C26A—H26A0.96C26B—H26D0.96
C26A—H26B0.96C26B—H26E0.96
C26A—H26C0.96C26B—H26F0.96
C12A—O1A—C11A109.42 (15)C12B—O1B—C11B109.53 (16)
C7A—N1A—N2A118.96 (15)C7B—N1B—N2B116.17 (13)
C14A—N2A—N1A118.48 (14)C14B—N2B—C8B108.67 (13)
C14A—N2A—C8A108.24 (14)C14B—N2B—N1B119.85 (13)
N1A—N2A—C8A132.91 (14)C8B—N2B—N1B131.46 (13)
C8A—N3A—N4A113.15 (14)C8B—N3B—N4B113.52 (13)
C8A—N3A—C9A127.36 (14)C8B—N3B—C9B125.58 (14)
N4A—N3A—C9A118.31 (14)N4B—N3B—C9B120.31 (13)
C14A—N4A—N3A105.00 (13)C14B—N4B—N3B104.42 (13)
C9A—N5A—C13A113.45 (14)C9B—N5B—C13B113.07 (14)
C9A—N5A—C10A114.09 (14)C9B—N5B—C10B113.21 (14)
C13A—N5A—C10A111.22 (14)C13B—N5B—C10B110.14 (15)
C2A—C1A—C6A120.34 (16)C2B—C1B—C6B120.78 (16)
C2A—C1A—H1AA119.8C2B—C1B—H1BA119.6
C6A—C1A—H1AA119.8C6B—C1B—H1BA119.6
C1A—C2A—C3A119.29 (17)C3B—C2B—C1B118.68 (16)
C1A—C2A—H2AA120.4C3B—C2B—H2BA120.7
C3A—C2A—H2AA120.4C1B—C2B—H2BA120.7
C4A—C3A—C2A121.59 (17)C2B—C3B—C4B121.87 (16)
C4A—C3A—Br1A118.94 (13)C2B—C3B—Br1B118.95 (13)
C2A—C3A—Br1A119.46 (13)C4B—C3B—Br1B119.18 (13)
C3A—C4A—C5A118.64 (16)C5B—C4B—C3B118.93 (15)
C3A—C4A—H4AA120.7C5B—C4B—H4BA120.5
C5A—C4A—H4AA120.7C3B—C4B—H4BA120.5
C4A—C5A—C6A120.98 (16)C4B—C5B—C6B120.32 (15)
C4A—C5A—H5AA119.5C4B—C5B—H5BA119.8
C6A—C5A—H5AA119.5C6B—C5B—H5BA119.8
C5A—C6A—C1A119.16 (16)C1B—C6B—C5B119.38 (15)
C5A—C6A—C7A118.04 (15)C1B—C6B—C7B118.38 (15)
C1A—C6A—C7A122.80 (16)C5B—C6B—C7B122.24 (15)
N1A—C7A—C6A119.92 (16)N1B—C7B—C6B120.00 (15)
N1A—C7A—H7AA120.0N1B—C7B—H7BA120.0
C6A—C7A—H7AA120.0C6B—C7B—H7BA120.0
N3A—C8A—N2A102.82 (14)N3B—C8B—N2B102.52 (13)
N3A—C8A—S1A126.71 (13)N3B—C8B—S1B127.83 (12)
N2A—C8A—S1A130.43 (13)N2B—C8B—S1B129.48 (12)
N5A—C9A—N3A116.28 (14)N5B—C9B—N3B114.70 (13)
N5A—C9A—H9AA108.2N5B—C9B—H9BA108.6
N3A—C9A—H9AA108.2N3B—C9B—H9BA108.6
N5A—C9A—H9AB108.2N5B—C9B—H9BB108.6
N3A—C9A—H9AB108.2N3B—C9B—H9BB108.6
H9AA—C9A—H9AB107.4H9BA—C9B—H9BB107.6
N5A—C10A—C11A110.09 (15)N5B—C10B—C11B109.00 (17)
N5A—C10A—H10A109.6N5B—C10B—H10C109.9
C11A—C10A—H10A109.6C11B—C10B—H10C109.9
N5A—C10A—H10B109.6N5B—C10B—H10D109.9
C11A—C10A—H10B109.6C11B—C10B—H10D109.9
H10A—C10A—H10B108.2H10C—C10B—H10D108.3
O1A—C11A—C10A110.79 (15)O1B—C11B—C10B111.30 (17)
O1A—C11A—H11A109.5O1B—C11B—H11C109.4
C10A—C11A—H11A109.5C10B—C11B—H11C109.4
O1A—C11A—H11B109.5O1B—C11B—H11D109.4
C10A—C11A—H11B109.5C10B—C11B—H11D109.4
H11A—C11A—H11B108.1H11C—C11B—H11D108.0
O1A—C12A—C13A110.22 (16)O1B—C12B—C13B111.70 (17)
O1A—C12A—H12A109.6O1B—C12B—H12C109.3
C13A—C12A—H12A109.6C13B—C12B—H12C109.3
O1A—C12A—H12B109.6O1B—C12B—H12D109.3
C13A—C12A—H12B109.6C13B—C12B—H12D109.3
H12A—C12A—H12B108.1H12C—C12B—H12D107.9
N5A—C13A—C12A109.19 (15)N5B—C13B—C12B110.45 (15)
N5A—C13A—H13A109.8N5B—C13B—H13C109.6
C12A—C13A—H13A109.8C12B—C13B—H13C109.6
N5A—C13A—H13B109.8N5B—C13B—H13D109.6
C12A—C13A—H13B109.8C12B—C13B—H13D109.6
H13A—C13A—H13B108.3H13C—C13B—H13D108.1
N4A—C14A—N2A110.74 (15)N4B—C14B—N2B110.69 (14)
N4A—C14A—C15A126.11 (15)N4B—C14B—C15B126.33 (14)
N2A—C14A—C15A123.15 (15)N2B—C14B—C15B122.97 (14)
C14A—C15A—C16A111.78 (14)C14B—C15B—C16B111.17 (13)
C14A—C15A—C26A110.46 (15)C14B—C15B—C26B110.32 (14)
C16A—C15A—C26A111.11 (14)C16B—C15B—C26B111.12 (13)
C14A—C15A—H15A107.8C14B—C15B—H15B108.0
C16A—C15A—H15A107.8C16B—C15B—H15B108.0
C26A—C15A—H15A107.8C26B—C15B—H15B108.0
C17A—C16A—C21A118.32 (16)C21B—C16B—C17B118.16 (16)
C17A—C16A—C15A120.15 (16)C21B—C16B—C15B120.75 (15)
C21A—C16A—C15A121.51 (16)C17B—C16B—C15B121.05 (14)
C18A—C17A—C16A120.44 (17)C18B—C17B—C16B120.85 (16)
C18A—C17A—H17A119.8C18B—C17B—H17B119.6
C16A—C17A—H17A119.8C16B—C17B—H17B119.6
C19A—C18A—C17A121.61 (17)C17B—C18B—C19B121.25 (16)
C19A—C18A—H18A119.2C17B—C18B—H18B119.4
C17A—C18A—H18A119.2C19B—C18B—H18B119.4
C18A—C19A—C20A117.92 (17)C18B—C19B—C20B117.74 (16)
C18A—C19A—C22A120.89 (17)C18B—C19B—C22B121.30 (16)
C20A—C19A—C22A121.20 (17)C20B—C19B—C22B120.97 (15)
C21A—C20A—C19A120.80 (16)C21B—C20B—C19B121.21 (16)
C21A—C20A—H20A119.6C21B—C20B—H20B119.4
C19A—C20A—H20A119.6C19B—C20B—H20B119.4
C20A—C21A—C16A120.90 (16)C20B—C21B—C16B120.78 (16)
C20A—C21A—H21A119.5C20B—C21B—H21B119.6
C16A—C21A—H21A119.5C16B—C21B—H21B119.6
C19A—C22A—C23A114.42 (17)C19B—C22B—C23B114.05 (13)
C19A—C22A—H22A108.7C19B—C22B—H22C108.7
C23A—C22A—H22A108.7C23B—C22B—H22C108.7
C19A—C22A—H22B108.7C19B—C22B—H22D108.7
C23A—C22A—H22B108.7C23B—C22B—H22D108.7
H22A—C22A—H22B107.6H22C—C22B—H22D107.6
C25A—C23A—C22A112.0 (2)C24B—C23B—C25B111.57 (14)
C25A—C23A—C24A111.9 (2)C24B—C23B—C22B110.81 (14)
C22A—C23A—C24A109.77 (19)C25B—C23B—C22B109.58 (14)
C25A—C23A—H23A107.7C24B—C23B—H23B108.3
C22A—C23A—H23A107.7C25B—C23B—H23B108.3
C24A—C23A—H23A107.7C22B—C23B—H23B108.3
C23A—C24A—H24A109.5C23B—C24B—H24D109.5
C23A—C24A—H24B109.5C23B—C24B—H24E109.5
H24A—C24A—H24B109.5H24D—C24B—H24E109.5
C23A—C24A—H24C109.5C23B—C24B—H24F109.5
H24A—C24A—H24C109.5H24D—C24B—H24F109.5
H24B—C24A—H24C109.5H24E—C24B—H24F109.5
C23A—C25A—H25A109.5C23B—C25B—H25D109.5
C23A—C25A—H25B109.5C23B—C25B—H25E109.5
H25A—C25A—H25B109.5H25D—C25B—H25E109.5
C23A—C25A—H25C109.5C23B—C25B—H25F109.5
H25A—C25A—H25C109.5H25D—C25B—H25F109.5
H25B—C25A—H25C109.5H25E—C25B—H25F109.5
C15A—C26A—H26A109.5C15B—C26B—H26D109.5
C15A—C26A—H26B109.5C15B—C26B—H26E109.5
H26A—C26A—H26B109.5H26D—C26B—H26E109.5
C15A—C26A—H26C109.5C15B—C26B—H26F109.5
H26A—C26A—H26C109.5H26D—C26B—H26F109.5
H26B—C26A—H26C109.5H26E—C26B—H26F109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7A—H7AA···S1A0.932.463.195 (2)137
C9A—H9AB···S1A0.972.863.252 (2)105
C4B—H4BA···N5Ai0.932.563.384 (2)147
C10A—H10A···Br1Aii0.972.863.770 (2)158
C7B—H7BA···S1B0.932.563.190 (2)125
C9B—H9BB···S1B0.972.853.254 (2)106
C15A—H15A···O1Aiii0.982.293.244 (2)165
C4A—H4AA···Cg1ii0.932.533.401 (2)156

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2634).

References

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