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Acta Crystallogr Sect E Struct Rep Online. Dec 1, 2011; 67(Pt 12): o3274.
Published online Nov 12, 2011. doi:  10.1107/S1600536811046514
PMCID: PMC3238931
7′-(4-Bromo­phen­yl)-5′,6′,7′,7a’-tetra­hydro­dispiro­[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione
Ang Chee Wei,a Mohamed Ashraf Ali,a Yeong Keng Yoon,a Ching Kheng Quah,b and Hoong-Kun Funb*§
aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun/at/usm.my
Thomson Reuters ResearcherID: A-5525-2009.
§Thomson Reuters ResearcherID: A-3561-2009.
Received November 1, 2011; Accepted November 4, 2011.
Abstract
In the title compound, C28H20BrNO3S, the thia­zolidine, pyrrolidine and two five-membered carbocyclic rings are in envelope conformations. The bromo-bound phenyl ring forms dihedral angles of 61.97 (18) and 88.30 (17)° with the other two benzene rings. The two benzene rings form a dihedral angle of 30.3 (2)°. The mol­ecular structure features an intra­molecular C—H(...)O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked into inversion dimers by pairs of C—H(...)O hydrogen bonds.
Related literature
For related structures and background references, see: Wei et al. (2011a [triangle],b [triangle],c [triangle]); Kumar et al. (2010 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).
An external file that holds a picture, illustration, etc.
Object name is e-67-o3274-scheme1.jpg Object name is e-67-o3274-scheme1.jpg
Crystal data
  • C28H20BrNO3S
  • M r = 530.42
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-67-o3274-efi1.jpg
  • a = 10.2871 (11) Å
  • b = 11.1375 (12) Å
  • c = 11.5877 (13) Å
  • α = 115.511 (2)°
  • β = 90.075 (2)°
  • γ = 97.347 (2)°
  • V = 1186.0 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.85 mm−1
  • T = 296 K
  • 0.31 × 0.13 × 0.05 mm
Data collection
  • Bruker SMART APEXII DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.599, T max = 0.915
  • 17888 measured reflections
  • 5422 independent reflections
  • 3789 reflections with I > 2σ(I)
  • R int = 0.028
Refinement
  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.136
  • S = 1.04
  • 5422 reflections
  • 307 parameters
  • H-atom parameters constrained
  • Δρmax = 0.76 e Å−3
  • Δρmin = −0.55 e Å−3
Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; 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, 2009 [triangle]).
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046514/hg5131sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046514/hg5131Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors wish to express their thanks to Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Mol­ecular Medicine, Universiti Sains Malysia (USM), Penang; this work was funded through Research Grant No. RUC (1001/PSK/8620012). HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).
supplementary crystallographic information
Comment
As part of our ongoing search for novel heterocyclic compounds with antitubercular activity (Wei et al., 2011a, 2011b, 2011c), our group has synthesized the title compound as described below.
The molecular structure is shown in Fig. 1. The thiazolidine (S1/N1/C26-C28), pyrrolidine (N1/C9/C10/C19/C26) and two five-membered carbocyclic (C1/C2/C7-C9 and C10-C12/C17/C18) rings are in envelope conformations, puckering parameters (Cremer & Pople, 1975) Q = 0.373 (3) Å and [var phi] = 31.3 (5)° with atom C27 at the flap; Q = 0.456 (3) Å and [var phi] = 243.8 (4)° with atom C10 at the flap; Q = 0.229 (4) Å and [var phi] = 330.0 (9)° with atom C9 at the flap; and Q = 0.168 (3) Å and [var phi] = 171.2 (12)° with atom C10 at the flap, respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Kumar et al., 2010; Wei et al., 2011a,b,c). The bromo-bound phenyl (C20-C25) ring forms dihedral angles of 61.97 (18) and 88.30 (17)° with the other two phenyl (C2-C7 and C12-C17) rings, respectively. The two phenyl rings form a dihedral angle of 30.3 (2)°. The molecular structure is stabilized by an intramolecular C18–H18B···O1 hydrogen bond (Table 1), which generates an S(6) ring motif (Fig. 1, Bernstein et al., 1995).
In the crystal (Fig. 2), molecules are linked into inversion dimers by pairs of intermolecular C22–H22A···O2 hydrogen bonds (Table 1).
Experimental
A mixture of (Z)2-(4-bromobenzylidene)-2,3-dihydro-1H-indene-1-one (0.298gm, 0.001 mol), ninhydrin (0.178gm, 0.001 mol) and thiazolidine-4-carboxylic acid (0.266gm, 0.002 mol) (1:1:2) were dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice. The precipitated solid was filtered, washed and recrystallised from petroleum ether–ethyl acetate mixture (1:1) to afford the title compound as yellow crystals. M.p. : 487 K.
Refinement
All H atoms were positioned geometrically and refined using a riding model with C–H = 0.93-0.98 Å and Uiso(H) = 1.2 Ueq(C).
Figures
Fig. 1.
Fig. 1.
The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms. Intramolecular hydrogen bond is shown as dashed line.
Fig. 2.
Fig. 2.
The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.
Crystal data
C28H20BrNO3SZ = 2
Mr = 530.42F(000) = 540
Triclinic, P1Dx = 1.485 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2871 (11) ÅCell parameters from 5183 reflections
b = 11.1375 (12) Åθ = 2.7–25.1°
c = 11.5877 (13) ŵ = 1.85 mm1
α = 115.511 (2)°T = 296 K
β = 90.075 (2)°Plate, yellow
γ = 97.347 (2)°0.31 × 0.13 × 0.05 mm
V = 1186.0 (2) Å3
Data collection
Bruker SMART APEXII DUO CCD area-detector diffractometer5422 independent reflections
Radiation source: fine-focus sealed tube3789 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→13
Tmin = 0.599, Tmax = 0.915k = −14→14
17888 measured reflectionsl = −15→15
Refinement
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.069P)2 + 0.5361P] where P = (Fo2 + 2Fc2)/3
5422 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 0.76 e Å3
0 restraintsΔρmin = −0.55 e Å3
Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1−0.23515 (4)0.46981 (4)1.06048 (4)0.06794 (16)
S1−0.16572 (9)0.80844 (13)0.47197 (11)0.0762 (3)
O10.3178 (2)0.7025 (2)0.4532 (2)0.0603 (6)
O20.0988 (2)1.0386 (2)0.7289 (2)0.0534 (5)
O30.2534 (2)0.9395 (2)0.9235 (2)0.0541 (6)
N10.0550 (2)0.7507 (2)0.5431 (2)0.0386 (5)
C10.3018 (3)0.7992 (3)0.5499 (3)0.0433 (6)
C20.3960 (3)0.9234 (3)0.6201 (3)0.0448 (7)
C30.5303 (3)0.9444 (4)0.6109 (4)0.0635 (9)
H3A0.57420.87550.55620.076*
C40.5965 (4)1.0703 (5)0.6853 (5)0.0809 (13)
H4A0.68711.08660.68290.097*
C50.5297 (4)1.1739 (5)0.7641 (5)0.0828 (13)
H5A0.57661.25880.81180.099*
C60.3960 (4)1.1540 (4)0.7733 (3)0.0614 (9)
H6A0.35191.22370.82640.074*
C70.3297 (3)1.0265 (3)0.7008 (3)0.0446 (7)
C80.1887 (3)0.9741 (3)0.6930 (3)0.0394 (6)
C90.1741 (2)0.8187 (3)0.6216 (3)0.0353 (6)
C100.1681 (2)0.7534 (3)0.7189 (2)0.0341 (5)
C110.2667 (3)0.8332 (3)0.8357 (3)0.0384 (6)
C120.3772 (3)0.7561 (3)0.8172 (3)0.0398 (6)
C130.4989 (3)0.7948 (4)0.8868 (3)0.0552 (8)
H13A0.51800.87770.95760.066*
C140.5894 (3)0.7062 (4)0.8473 (4)0.0717 (11)
H14A0.67170.72970.89060.086*
C150.5583 (3)0.5823 (4)0.7433 (4)0.0686 (10)
H15A0.62030.52350.71870.082*
C160.4386 (3)0.5428 (3)0.6747 (3)0.0529 (8)
H16A0.41950.45890.60520.064*
C170.3475 (3)0.6321 (3)0.7127 (3)0.0375 (6)
C180.2104 (3)0.6122 (3)0.6556 (3)0.0386 (6)
H18A0.15250.54880.67560.046*
H18B0.20990.57950.56330.046*
C190.0224 (2)0.7599 (3)0.7500 (3)0.0358 (6)
H19A0.01520.85460.80370.043*
C20−0.0338 (2)0.6824 (3)0.8229 (3)0.0356 (6)
C21−0.0347 (3)0.7498 (3)0.9562 (3)0.0442 (7)
H21A0.00240.83960.99820.053*
C22−0.0899 (3)0.6850 (3)1.0270 (3)0.0487 (7)
H22A−0.08810.73011.11580.058*
C23−0.1472 (3)0.5537 (3)0.9644 (3)0.0429 (6)
C24−0.1460 (3)0.4830 (3)0.8343 (3)0.0409 (6)
H24A−0.18270.39300.79360.049*
C25−0.0886 (3)0.5483 (3)0.7640 (3)0.0381 (6)
H25A−0.08710.50090.67560.046*
C26−0.0479 (3)0.7231 (3)0.6201 (3)0.0414 (6)
H26A−0.08290.62720.58000.050*
C27−0.1579 (3)0.8053 (4)0.6265 (4)0.0647 (10)
H27A−0.13780.89570.69470.078*
H27B−0.24060.76330.64140.078*
C280.0078 (3)0.8013 (3)0.4550 (3)0.0470 (7)
H28A0.02330.74200.36750.056*
H28B0.05440.89020.47550.056*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
Br10.0633 (3)0.0906 (3)0.0682 (3)0.00456 (19)0.01299 (18)0.0533 (2)
S10.0400 (5)0.1299 (9)0.0944 (7)0.0093 (5)−0.0060 (4)0.0830 (7)
O10.0624 (15)0.0585 (14)0.0492 (13)0.0145 (11)0.0144 (11)0.0115 (12)
O20.0492 (13)0.0408 (11)0.0637 (14)0.0105 (10)0.0092 (10)0.0156 (10)
O30.0513 (13)0.0450 (12)0.0475 (12)0.0035 (10)−0.0079 (10)0.0036 (10)
N10.0365 (12)0.0402 (12)0.0399 (12)0.0020 (10)−0.0049 (9)0.0192 (10)
C10.0411 (16)0.0490 (17)0.0414 (16)0.0090 (13)0.0064 (12)0.0204 (14)
C20.0369 (15)0.0549 (18)0.0472 (16)0.0011 (13)0.0006 (12)0.0278 (14)
C30.0393 (18)0.090 (3)0.072 (2)0.0106 (18)0.0107 (16)0.045 (2)
C40.040 (2)0.116 (4)0.096 (3)−0.018 (2)−0.011 (2)0.063 (3)
C50.066 (3)0.079 (3)0.089 (3)−0.035 (2)−0.017 (2)0.035 (2)
C60.061 (2)0.0531 (19)0.058 (2)−0.0120 (16)−0.0053 (16)0.0178 (16)
C70.0436 (16)0.0438 (16)0.0460 (16)−0.0044 (13)−0.0024 (13)0.0222 (14)
C80.0393 (15)0.0374 (14)0.0387 (14)0.0034 (12)0.0023 (12)0.0146 (12)
C90.0320 (13)0.0341 (13)0.0376 (14)0.0034 (10)0.0018 (11)0.0139 (11)
C100.0291 (13)0.0329 (13)0.0367 (14)0.0004 (10)−0.0031 (10)0.0128 (11)
C110.0377 (15)0.0356 (14)0.0361 (14)−0.0047 (11)−0.0079 (11)0.0130 (12)
C120.0316 (14)0.0457 (16)0.0398 (15)−0.0003 (11)−0.0017 (11)0.0180 (13)
C130.0404 (17)0.062 (2)0.0557 (19)−0.0019 (15)−0.0151 (14)0.0210 (16)
C140.0359 (18)0.098 (3)0.084 (3)0.0115 (18)−0.0127 (17)0.041 (2)
C150.0449 (19)0.082 (3)0.080 (3)0.0274 (18)0.0018 (18)0.031 (2)
C160.0449 (17)0.0545 (19)0.0543 (19)0.0165 (14)0.0028 (14)0.0164 (15)
C170.0292 (13)0.0425 (15)0.0416 (15)0.0038 (11)0.0000 (11)0.0193 (12)
C180.0345 (14)0.0357 (14)0.0415 (15)0.0006 (11)−0.0058 (11)0.0143 (12)
C190.0306 (13)0.0335 (13)0.0403 (14)0.0015 (10)−0.0013 (11)0.0142 (12)
C200.0267 (13)0.0398 (14)0.0413 (15)0.0041 (10)−0.0007 (10)0.0187 (12)
C210.0433 (16)0.0401 (15)0.0409 (16)0.0037 (12)−0.0005 (12)0.0104 (13)
C220.0507 (18)0.0543 (18)0.0356 (15)0.0088 (14)0.0025 (13)0.0140 (14)
C230.0340 (14)0.0562 (18)0.0476 (16)0.0092 (13)0.0067 (12)0.0303 (14)
C240.0369 (15)0.0392 (15)0.0448 (16)0.0013 (12)0.0003 (12)0.0178 (13)
C250.0342 (14)0.0402 (15)0.0361 (14)0.0030 (11)0.0004 (11)0.0136 (12)
C260.0363 (15)0.0441 (15)0.0459 (16)−0.0039 (12)−0.0080 (12)0.0242 (13)
C270.0330 (16)0.107 (3)0.082 (3)0.0131 (17)0.0047 (15)0.066 (2)
C280.0449 (16)0.0556 (18)0.0474 (17)0.0091 (14)−0.0008 (13)0.0284 (15)
Geometric parameters (Å, °)
Br1—C231.901 (3)C13—C141.377 (5)
S1—C281.805 (3)C13—H13A0.9300
S1—C271.808 (4)C14—C151.383 (6)
O1—C11.204 (4)C14—H14A0.9300
O2—C81.208 (3)C15—C161.378 (5)
O3—C111.209 (3)C15—H15A0.9300
N1—C91.439 (3)C16—C171.387 (4)
N1—C281.469 (4)C16—H16A0.9300
N1—C261.473 (4)C17—C181.505 (4)
C1—C21.483 (4)C18—H18A0.9700
C1—C91.543 (4)C18—H18B0.9700
C2—C31.383 (4)C19—C201.514 (4)
C2—C71.391 (4)C19—C261.531 (4)
C3—C41.374 (6)C19—H19A0.9800
C3—H3A0.9300C20—C251.386 (4)
C4—C51.390 (7)C20—C211.397 (4)
C4—H4A0.9300C21—C221.387 (4)
C5—C61.377 (6)C21—H21A0.9300
C5—H5A0.9300C22—C231.370 (4)
C6—C71.383 (4)C22—H22A0.9300
C6—H6A0.9300C23—C241.368 (4)
C7—C81.480 (4)C24—C251.395 (4)
C8—C91.551 (4)C24—H24A0.9300
C9—C101.580 (4)C25—H25A0.9300
C10—C111.543 (4)C26—C271.526 (4)
C10—C181.544 (4)C26—H26A0.9800
C10—C191.546 (4)C27—H27A0.9700
C11—C121.471 (4)C27—H27B0.9700
C12—C171.385 (4)C28—H28A0.9700
C12—C131.402 (4)C28—H28B0.9700
C28—S1—C2792.49 (14)C15—C16—C17117.9 (3)
C9—N1—C28119.0 (2)C15—C16—H16A121.1
C9—N1—C26110.4 (2)C17—C16—H16A121.1
C28—N1—C26113.6 (2)C12—C17—C16120.3 (3)
O1—C1—C2127.6 (3)C12—C17—C18111.6 (2)
O1—C1—C9125.5 (3)C16—C17—C18128.1 (3)
C2—C1—C9106.8 (2)C17—C18—C10104.2 (2)
C3—C2—C7121.3 (3)C17—C18—H18A110.9
C3—C2—C1128.7 (3)C10—C18—H18A110.9
C7—C2—C1110.0 (2)C17—C18—H18B110.9
C4—C3—C2117.7 (4)C10—C18—H18B110.9
C4—C3—H3A121.1H18A—C18—H18B108.9
C2—C3—H3A121.1C20—C19—C26116.1 (2)
C3—C4—C5120.9 (3)C20—C19—C10116.8 (2)
C3—C4—H4A119.6C26—C19—C10103.4 (2)
C5—C4—H4A119.6C20—C19—H19A106.6
C6—C5—C4121.7 (4)C26—C19—H19A106.6
C6—C5—H5A119.1C10—C19—H19A106.6
C4—C5—H5A119.1C25—C20—C21117.8 (3)
C5—C6—C7117.4 (4)C25—C20—C19123.4 (2)
C5—C6—H6A121.3C21—C20—C19118.8 (2)
C7—C6—H6A121.3C22—C21—C20121.1 (3)
C6—C7—C2120.9 (3)C22—C21—H21A119.5
C6—C7—C8129.8 (3)C20—C21—H21A119.5
C2—C7—C8109.3 (2)C23—C22—C21119.2 (3)
O2—C8—C7127.3 (3)C23—C22—H22A120.4
O2—C8—C9125.0 (2)C21—C22—H22A120.4
C7—C8—C9107.6 (2)C24—C23—C22121.7 (3)
N1—C9—C1115.4 (2)C24—C23—Br1119.3 (2)
N1—C9—C8117.0 (2)C22—C23—Br1119.0 (2)
C1—C9—C8101.0 (2)C23—C24—C25118.8 (3)
N1—C9—C10101.06 (19)C23—C24—H24A120.6
C1—C9—C10111.5 (2)C25—C24—H24A120.6
C8—C9—C10111.2 (2)C20—C25—C24121.5 (3)
C11—C10—C18104.5 (2)C20—C25—H25A119.3
C11—C10—C19114.4 (2)C24—C25—H25A119.3
C18—C10—C19116.7 (2)N1—C26—C27108.7 (2)
C11—C10—C9111.9 (2)N1—C26—C19104.9 (2)
C18—C10—C9110.4 (2)C27—C26—C19114.3 (3)
C19—C10—C999.1 (2)N1—C26—H26A109.6
O3—C11—C12128.0 (2)C27—C26—H26A109.6
O3—C11—C10125.1 (3)C19—C26—H26A109.6
C12—C11—C10107.0 (2)C26—C27—S1104.9 (2)
C17—C12—C13121.3 (3)C26—C27—H27A110.8
C17—C12—C11109.8 (2)S1—C27—H27A110.8
C13—C12—C11128.8 (3)C26—C27—H27B110.8
C14—C13—C12118.0 (3)S1—C27—H27B110.8
C14—C13—H13A121.0H27A—C27—H27B108.9
C12—C13—H13A121.0N1—C28—S1108.2 (2)
C13—C14—C15120.1 (3)N1—C28—H28A110.1
C13—C14—H14A119.9S1—C28—H28A110.1
C15—C14—H14A119.9N1—C28—H28B110.1
C16—C15—C14122.4 (3)S1—C28—H28B110.1
C16—C15—H15A118.8H28A—C28—H28B108.4
C14—C15—H15A118.8
O1—C1—C2—C3−17.4 (5)C10—C11—C12—C17−8.1 (3)
C9—C1—C2—C3164.9 (3)O3—C11—C12—C13−9.1 (5)
O1—C1—C2—C7161.0 (3)C10—C11—C12—C13170.2 (3)
C9—C1—C2—C7−16.6 (3)C17—C12—C13—C140.8 (5)
C7—C2—C3—C40.7 (5)C11—C12—C13—C14−177.2 (3)
C1—C2—C3—C4179.0 (3)C12—C13—C14—C15−1.3 (6)
C2—C3—C4—C5−1.9 (6)C13—C14—C15—C160.8 (7)
C3—C4—C5—C61.7 (7)C14—C15—C16—C170.2 (6)
C4—C5—C6—C7−0.1 (6)C13—C12—C17—C160.2 (4)
C5—C6—C7—C2−1.1 (5)C11—C12—C17—C16178.5 (3)
C5—C6—C7—C8178.3 (3)C13—C12—C17—C18178.6 (3)
C3—C2—C7—C60.8 (5)C11—C12—C17—C18−3.0 (3)
C1—C2—C7—C6−177.8 (3)C15—C16—C17—C12−0.7 (5)
C3—C2—C7—C8−178.7 (3)C15—C16—C17—C18−178.8 (3)
C1—C2—C7—C82.7 (3)C12—C17—C18—C1012.7 (3)
C6—C7—C8—O216.4 (5)C16—C17—C18—C10−169.0 (3)
C2—C7—C8—O2−164.2 (3)C11—C10—C18—C17−16.5 (3)
C6—C7—C8—C9−167.2 (3)C19—C10—C18—C17−143.9 (2)
C2—C7—C8—C912.2 (3)C9—C10—C18—C17104.0 (2)
C28—N1—C9—C1−71.8 (3)C11—C10—C19—C20−72.1 (3)
C26—N1—C9—C1154.2 (2)C18—C10—C19—C2050.3 (3)
C28—N1—C9—C846.8 (3)C9—C10—C19—C20168.7 (2)
C26—N1—C9—C8−87.2 (3)C11—C10—C19—C26159.1 (2)
C28—N1—C9—C10167.7 (2)C18—C10—C19—C26−78.6 (3)
C26—N1—C9—C1033.7 (3)C9—C10—C19—C2639.9 (2)
O1—C1—C9—N1−28.3 (4)C26—C19—C20—C2535.0 (4)
C2—C1—C9—N1149.5 (2)C10—C19—C20—C25−87.5 (3)
O1—C1—C9—C8−155.4 (3)C26—C19—C20—C21−142.9 (3)
C2—C1—C9—C822.3 (3)C10—C19—C20—C2194.7 (3)
O1—C1—C9—C1086.3 (3)C25—C20—C21—C22−0.7 (4)
C2—C1—C9—C10−96.0 (3)C19—C20—C21—C22177.3 (3)
O2—C8—C9—N129.4 (4)C20—C21—C22—C23−1.6 (5)
C7—C8—C9—N1−147.0 (2)C21—C22—C23—C243.1 (5)
O2—C8—C9—C1155.6 (3)C21—C22—C23—Br1−175.0 (2)
C7—C8—C9—C1−20.9 (3)C22—C23—C24—C25−2.2 (4)
O2—C8—C9—C10−85.9 (3)Br1—C23—C24—C25175.9 (2)
C7—C8—C9—C1097.6 (3)C21—C20—C25—C241.6 (4)
N1—C9—C10—C11−165.7 (2)C19—C20—C25—C24−176.3 (2)
C1—C9—C10—C1171.2 (3)C23—C24—C25—C20−0.2 (4)
C8—C9—C10—C11−40.8 (3)C9—N1—C26—C27114.1 (3)
N1—C9—C10—C1878.4 (2)C28—N1—C26—C27−22.5 (3)
C1—C9—C10—C18−44.8 (3)C9—N1—C26—C19−8.5 (3)
C8—C9—C10—C18−156.8 (2)C28—N1—C26—C19−145.1 (2)
N1—C9—C10—C19−44.6 (2)C20—C19—C26—N1−150.6 (2)
C1—C9—C10—C19−167.8 (2)C10—C19—C26—N1−21.3 (3)
C8—C9—C10—C1980.2 (2)C20—C19—C26—C2790.6 (3)
C18—C10—C11—O3−165.4 (3)C10—C19—C26—C27−140.1 (2)
C19—C10—C11—O3−36.6 (4)N1—C26—C27—S135.1 (3)
C9—C10—C11—O375.1 (3)C19—C26—C27—S1151.8 (2)
C18—C10—C11—C1215.4 (3)C28—S1—C27—C26−31.1 (3)
C19—C10—C11—C12144.1 (2)C9—N1—C28—S1−133.7 (2)
C9—C10—C11—C12−104.2 (2)C26—N1—C28—S1−1.1 (3)
O3—C11—C12—C17172.7 (3)C27—S1—C28—N119.3 (2)
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
C18—H18B···O10.972.423.080 (4)125.
C22—H22A···O2i0.932.443.172 (4)135.
Symmetry codes: (i) −x, −y+2, −z+2.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5131).
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