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In the title structure, C15H9Cl2F3N2OS, there are two independent mol­ecules in the asymmetric unit, both of which show typical geometric parameters for substituted thio­urea derivatives. The dihedral angles formed by the two benzene ring planes are 52.7 (2) and 57.6 (2)° for the two mol­ecules. The crystal structure is stabilized by N—H...O and N—H...S hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035185/lh2169sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035185/lh2169Isup2.hkl
Contains datablock I

CCDC reference: 624906

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.067
  • wR factor = 0.155
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT213_ALERT_2_C Atom F2 has ADP max/min Ratio ............. 3.20 prola PLAT213_ALERT_2_C Atom F2A has ADP max/min Ratio ............. 3.10 prola PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27A PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT430_ALERT_2_C Short Inter D...A Contact O1 .. O1A .. 2.89 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

1-(2,6-Dichlorobenzoyl)-3-[(3-trifluoromethyl)phenyl]thiourea top
Crystal data top
C15H9Cl2F3N2OSF(000) = 1584
Mr = 393.20Dx = 1.598 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11595 reflections
a = 16.1754 (12) Åθ = 3.6–25.8°
b = 13.6250 (13) ŵ = 0.56 mm1
c = 16.2839 (12) ÅT = 173 K
β = 114.358 (5)°Plate, colourless
V = 3269.4 (5) Å30.23 × 0.20 × 0.08 mm
Z = 8
Data collection top
Stoe IPDSII two-circle
diffractometer
5993 independent reflections
Radiation source: fine-focus sealed tube4655 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
ω scansθmax = 25.4°, θmin = 1.4°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1917
Tmin = 0.882, Tmax = 0.957k = 016
15119 measured reflectionsl = 019
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.155 w = 1/[σ2(Fo2) + (0.0048P)2 + 19.2275P]
where P = (Fo2 + 2Fc2)/3
S = 1.19(Δ/σ)max < 0.001
5993 reflectionsΔρmax = 0.54 e Å3
434 parametersΔρmin = 0.39 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0029 (3)
Special details top

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) top
xyzUiso*/Ueq
C10.4912 (3)0.2492 (4)0.4895 (3)0.0181 (11)
O10.4582 (2)0.1754 (3)0.4447 (2)0.0233 (8)
N10.4440 (3)0.3331 (3)0.4859 (3)0.0168 (9)
H10.47470.38060.52220.020*
C20.3517 (3)0.3535 (4)0.4310 (3)0.0176 (10)
S10.30771 (9)0.45945 (10)0.44664 (9)0.0230 (3)
N20.3083 (3)0.2844 (3)0.3704 (3)0.0202 (10)
H20.34030.23310.36810.024*
C110.5907 (3)0.2538 (4)0.5542 (3)0.0169 (10)
C120.6198 (4)0.2260 (4)0.6449 (3)0.0210 (11)
C130.7109 (4)0.2278 (5)0.7031 (4)0.0317 (14)
H130.72980.20730.76390.038*
C140.7744 (4)0.2598 (5)0.6719 (4)0.0340 (15)
H140.83670.26320.71210.041*
C150.7472 (4)0.2869 (4)0.5820 (4)0.0291 (13)
H150.79070.30770.56050.035*
C160.6557 (4)0.2829 (4)0.5243 (3)0.0198 (11)
Cl10.53867 (10)0.18932 (13)0.68302 (9)0.0354 (4)
Cl20.62157 (9)0.31470 (10)0.41169 (9)0.0256 (3)
C210.2138 (3)0.2858 (4)0.3084 (3)0.0209 (11)
C220.1653 (3)0.1999 (4)0.2986 (3)0.0221 (11)
H220.19340.14430.33450.027*
C230.0746 (4)0.1948 (4)0.2358 (4)0.0252 (12)
C240.0336 (4)0.2764 (5)0.1838 (4)0.0346 (15)
H240.02800.27370.14160.042*
C250.0833 (4)0.3615 (5)0.1941 (4)0.0367 (15)
H250.05530.41690.15790.044*
C260.1741 (4)0.3682 (5)0.2567 (4)0.0300 (13)
H260.20750.42730.26360.036*
C270.0229 (4)0.1028 (5)0.2294 (5)0.0388 (16)
F10.0030 (4)0.0947 (4)0.2972 (4)0.095 (2)
F20.0523 (3)0.0963 (4)0.1541 (4)0.0820 (18)
F30.0706 (3)0.0219 (3)0.2338 (3)0.0603 (13)
C1A0.6742 (3)0.5986 (4)0.3072 (3)0.0171 (10)
O1A0.6653 (2)0.5993 (3)0.2285 (2)0.0259 (9)
C2A0.5138 (3)0.5511 (4)0.2789 (3)0.0167 (10)
S1A0.44833 (9)0.51787 (10)0.33068 (8)0.0213 (3)
N1A0.6064 (3)0.5703 (3)0.3323 (3)0.0176 (9)
H1A0.62330.56290.39070.021*
N2A0.4884 (3)0.5620 (3)0.1889 (3)0.0197 (9)
H2A0.53160.57740.17170.024*
C11A0.7603 (3)0.6319 (4)0.3848 (3)0.0201 (11)
C12A0.7714 (4)0.7308 (4)0.4093 (4)0.0254 (12)
C13A0.8502 (4)0.7646 (5)0.4804 (4)0.0374 (15)
H13A0.85650.83190.49700.045*
C14A0.9193 (4)0.6981 (5)0.5262 (4)0.0378 (16)
H14A0.97330.72030.57420.045*
C15A0.9102 (4)0.6006 (5)0.5027 (4)0.0352 (15)
H15A0.95750.55560.53470.042*
C16A0.8313 (3)0.5677 (4)0.4317 (4)0.0223 (11)
Cl1A0.68536 (11)0.81353 (12)0.35141 (13)0.0433 (4)
Cl2A0.82049 (10)0.44332 (11)0.40404 (12)0.0392 (4)
C21A0.3993 (3)0.5512 (4)0.1191 (3)0.0189 (11)
C22A0.3215 (3)0.5811 (4)0.1285 (3)0.0211 (11)
H22A0.32510.60770.18390.025*
C23A0.2377 (3)0.5712 (4)0.0544 (3)0.0201 (11)
C24A0.2311 (4)0.5359 (4)0.0286 (4)0.0260 (12)
H24A0.17400.53230.07880.031*
C25A0.3099 (4)0.5062 (4)0.0360 (4)0.0275 (13)
H25A0.30660.48070.09160.033*
C26A0.3935 (4)0.5135 (4)0.0373 (4)0.0226 (11)
H26A0.44690.49260.03170.027*
C27A0.1544 (4)0.6051 (5)0.0649 (4)0.0285 (13)
F1A0.1407 (3)0.7028 (3)0.0518 (4)0.0675 (14)
F2A0.0785 (2)0.5633 (4)0.0074 (3)0.0676 (15)
F3A0.1574 (2)0.5900 (4)0.1465 (3)0.0522 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.016 (3)0.024 (3)0.013 (2)0.005 (2)0.006 (2)0.004 (2)
O10.0196 (19)0.019 (2)0.0246 (19)0.0011 (15)0.0022 (15)0.0082 (16)
N10.015 (2)0.015 (2)0.018 (2)0.0013 (17)0.0038 (17)0.0036 (17)
C20.021 (3)0.020 (3)0.013 (2)0.000 (2)0.009 (2)0.002 (2)
S10.0246 (7)0.0240 (7)0.0184 (6)0.0080 (6)0.0069 (5)0.0017 (5)
N20.008 (2)0.023 (2)0.021 (2)0.0033 (17)0.0012 (17)0.0034 (18)
C110.015 (2)0.017 (3)0.015 (2)0.004 (2)0.003 (2)0.004 (2)
C120.024 (3)0.024 (3)0.014 (2)0.001 (2)0.006 (2)0.000 (2)
C130.030 (3)0.035 (4)0.018 (3)0.004 (3)0.002 (2)0.004 (2)
C140.017 (3)0.046 (4)0.030 (3)0.000 (3)0.000 (2)0.008 (3)
C150.020 (3)0.032 (3)0.037 (3)0.004 (2)0.013 (2)0.003 (3)
C160.024 (3)0.016 (3)0.021 (3)0.001 (2)0.011 (2)0.003 (2)
Cl10.0369 (8)0.0481 (10)0.0233 (7)0.0093 (7)0.0147 (6)0.0030 (7)
Cl20.0319 (7)0.0270 (7)0.0212 (6)0.0014 (6)0.0142 (6)0.0029 (5)
C210.013 (3)0.031 (3)0.014 (2)0.009 (2)0.001 (2)0.001 (2)
C220.019 (3)0.023 (3)0.021 (3)0.004 (2)0.005 (2)0.001 (2)
C230.022 (3)0.029 (3)0.026 (3)0.001 (2)0.011 (2)0.004 (2)
C240.026 (3)0.044 (4)0.025 (3)0.006 (3)0.001 (2)0.004 (3)
C250.030 (3)0.033 (4)0.030 (3)0.012 (3)0.004 (3)0.006 (3)
C260.027 (3)0.030 (3)0.024 (3)0.002 (3)0.001 (2)0.004 (2)
C270.023 (3)0.042 (4)0.048 (4)0.000 (3)0.011 (3)0.008 (3)
F10.120 (5)0.091 (4)0.121 (5)0.058 (4)0.098 (4)0.034 (4)
F20.034 (2)0.059 (3)0.100 (4)0.013 (2)0.026 (2)0.006 (3)
F30.036 (2)0.034 (2)0.100 (4)0.0015 (18)0.017 (2)0.004 (2)
C1A0.013 (2)0.017 (3)0.019 (2)0.002 (2)0.005 (2)0.001 (2)
O1A0.0180 (19)0.042 (2)0.0163 (18)0.0030 (17)0.0057 (15)0.0012 (17)
C2A0.017 (2)0.016 (3)0.018 (2)0.002 (2)0.008 (2)0.001 (2)
S1A0.0162 (6)0.0300 (8)0.0174 (6)0.0042 (5)0.0067 (5)0.0037 (5)
N1A0.011 (2)0.026 (2)0.0140 (19)0.0035 (17)0.0031 (16)0.0024 (18)
N2A0.016 (2)0.027 (2)0.016 (2)0.0041 (18)0.0063 (17)0.0006 (18)
C11A0.016 (3)0.027 (3)0.016 (2)0.006 (2)0.006 (2)0.003 (2)
C12A0.020 (3)0.028 (3)0.028 (3)0.000 (2)0.011 (2)0.002 (2)
C13A0.036 (4)0.033 (4)0.038 (3)0.007 (3)0.011 (3)0.016 (3)
C14A0.023 (3)0.051 (4)0.030 (3)0.011 (3)0.001 (3)0.012 (3)
C15A0.020 (3)0.045 (4)0.029 (3)0.003 (3)0.002 (2)0.006 (3)
C16A0.015 (3)0.024 (3)0.026 (3)0.003 (2)0.006 (2)0.002 (2)
Cl1A0.0308 (8)0.0281 (8)0.0666 (11)0.0078 (7)0.0156 (8)0.0044 (8)
Cl2A0.0279 (8)0.0256 (8)0.0530 (9)0.0014 (6)0.0057 (7)0.0020 (7)
C21A0.021 (3)0.017 (3)0.019 (2)0.004 (2)0.009 (2)0.001 (2)
C22A0.020 (3)0.021 (3)0.017 (2)0.003 (2)0.003 (2)0.001 (2)
C23A0.015 (2)0.023 (3)0.020 (2)0.001 (2)0.004 (2)0.005 (2)
C24A0.022 (3)0.029 (3)0.018 (3)0.002 (2)0.001 (2)0.000 (2)
C25A0.031 (3)0.031 (3)0.018 (3)0.010 (3)0.006 (2)0.005 (2)
C26A0.025 (3)0.019 (3)0.027 (3)0.002 (2)0.014 (2)0.002 (2)
C27A0.018 (3)0.034 (3)0.027 (3)0.001 (2)0.004 (2)0.003 (3)
F1A0.057 (3)0.043 (3)0.120 (4)0.023 (2)0.055 (3)0.023 (3)
F2A0.0163 (19)0.112 (4)0.063 (3)0.014 (2)0.0053 (18)0.034 (3)
F3A0.031 (2)0.092 (4)0.041 (2)0.018 (2)0.0216 (17)0.017 (2)
Geometric parameters (Å, º) top
C1—O11.227 (6)C1A—O1A1.230 (6)
C1—N11.363 (7)C1A—N1A1.374 (6)
C1—C111.518 (7)C1A—C11A1.515 (7)
N1—C21.416 (6)C2A—N2A1.357 (6)
N1—H10.8800C2A—N1A1.412 (6)
C2—N21.334 (7)C2A—S1A1.666 (5)
C2—S11.675 (5)N1A—H1A0.8800
N2—C211.443 (6)N2A—C21A1.428 (6)
N2—H20.8800N2A—H2A0.8800
C11—C161.385 (7)C11A—C16A1.395 (8)
C11—C121.405 (7)C11A—C12A1.396 (8)
C12—C131.385 (8)C12A—C13A1.401 (8)
C12—Cl11.740 (6)C12A—Cl1A1.736 (6)
C13—C141.391 (9)C13A—C14A1.393 (10)
C13—H130.9500C13A—H13A0.9500
C14—C151.393 (9)C14A—C15A1.373 (10)
C14—H140.9500C14A—H14A0.9500
C15—C161.390 (8)C15A—C16A1.396 (8)
C15—H150.9500C15A—H15A0.9500
C16—Cl21.738 (5)C16A—Cl2A1.743 (6)
C21—C221.382 (8)C21A—C22A1.391 (7)
C21—C261.391 (8)C21A—C26A1.394 (7)
C22—C231.401 (7)C22A—C23A1.402 (7)
C22—H220.9500C22A—H22A0.9500
C23—C241.389 (8)C23A—C24A1.396 (8)
C23—C271.487 (9)C23A—C27A1.499 (8)
C24—C251.380 (9)C24A—C25A1.390 (8)
C24—H240.9500C24A—H24A0.9500
C25—C261.404 (8)C25A—C26A1.390 (8)
C25—H250.9500C25A—H25A0.9500
C26—H260.9500C26A—H26A0.9500
C27—F21.327 (8)C27A—F3A1.325 (7)
C27—F31.330 (8)C27A—F2A1.326 (7)
C27—F11.337 (8)C27A—F1A1.353 (7)
O1—C1—N1124.2 (5)O1A—C1A—N1A123.3 (4)
O1—C1—C11121.6 (5)O1A—C1A—C11A122.6 (4)
N1—C1—C11114.2 (4)N1A—C1A—C11A114.1 (4)
C1—N1—C2128.2 (4)N2A—C2A—N1A114.7 (4)
C1—N1—H1115.9N2A—C2A—S1A127.1 (4)
C2—N1—H1115.9N1A—C2A—S1A118.2 (4)
N2—C2—N1115.1 (4)C1A—N1A—C2A130.0 (4)
N2—C2—S1126.4 (4)C1A—N1A—H1A115.0
N1—C2—S1118.5 (4)C2A—N1A—H1A115.0
C2—N2—C21126.2 (5)C2A—N2A—C21A127.3 (4)
C2—N2—H2116.9C2A—N2A—H2A116.4
C21—N2—H2116.9C21A—N2A—H2A116.4
C16—C11—C12118.2 (5)C16A—C11A—C12A118.0 (5)
C16—C11—C1120.6 (4)C16A—C11A—C1A122.4 (5)
C12—C11—C1121.1 (5)C12A—C11A—C1A119.5 (5)
C13—C12—C11121.0 (5)C11A—C12A—C13A121.3 (5)
C13—C12—Cl1120.4 (4)C11A—C12A—Cl1A119.5 (4)
C11—C12—Cl1118.6 (4)C13A—C12A—Cl1A119.2 (5)
C12—C13—C14119.5 (5)C14A—C13A—C12A119.0 (6)
C12—C13—H13120.2C14A—C13A—H13A120.5
C14—C13—H13120.2C12A—C13A—H13A120.5
C13—C14—C15120.4 (5)C15A—C14A—C13A120.7 (6)
C13—C14—H14119.8C15A—C14A—H14A119.6
C15—C14—H14119.8C13A—C14A—H14A119.6
C16—C15—C14119.1 (5)C14A—C15A—C16A119.8 (6)
C16—C15—H15120.5C14A—C15A—H15A120.1
C14—C15—H15120.5C16A—C15A—H15A120.1
C11—C16—C15121.7 (5)C11A—C16A—C15A121.1 (5)
C11—C16—Cl2119.0 (4)C11A—C16A—Cl2A119.7 (4)
C15—C16—Cl2119.3 (4)C15A—C16A—Cl2A119.1 (4)
C22—C21—C26121.1 (5)C22A—C21A—C26A120.4 (5)
C22—C21—N2117.2 (5)C22A—C21A—N2A122.9 (5)
C26—C21—N2121.7 (5)C26A—C21A—N2A116.6 (5)
C21—C22—C23120.0 (5)C21A—C22A—C23A118.3 (5)
C21—C22—H22120.0C21A—C22A—H22A120.8
C23—C22—H22120.0C23A—C22A—H22A120.8
C24—C23—C22119.9 (5)C24A—C23A—C22A121.8 (5)
C24—C23—C27121.3 (5)C24A—C23A—C27A120.2 (5)
C22—C23—C27118.8 (5)C22A—C23A—C27A117.9 (5)
C25—C24—C23119.4 (5)C25A—C24A—C23A118.6 (5)
C25—C24—H24120.3C25A—C24A—H24A120.7
C23—C24—H24120.3C23A—C24A—H24A120.7
C24—C25—C26121.7 (6)C24A—C25A—C26A120.4 (5)
C24—C25—H25119.2C24A—C25A—H25A119.8
C26—C25—H25119.2C26A—C25A—H25A119.8
C21—C26—C25118.0 (6)C25A—C26A—C21A120.4 (5)
C21—C26—H26121.0C25A—C26A—H26A119.8
C25—C26—H26121.0C21A—C26A—H26A119.8
F2—C27—F3106.6 (6)F3A—C27A—F2A106.4 (5)
F2—C27—F1106.1 (6)F3A—C27A—F1A104.3 (5)
F3—C27—F1105.0 (6)F2A—C27A—F1A105.5 (5)
F2—C27—C23113.3 (6)F3A—C27A—C23A113.8 (5)
F3—C27—C23113.4 (5)F2A—C27A—C23A113.6 (5)
F1—C27—C23111.7 (6)F1A—C27A—C23A112.4 (5)
O1—C1—N1—C21.5 (8)O1A—C1A—N1A—C2A10.1 (9)
C11—C1—N1—C2178.0 (4)C11A—C1A—N1A—C2A168.1 (5)
C1—N1—C2—N26.0 (7)N2A—C2A—N1A—C1A0.4 (8)
C1—N1—C2—S1174.4 (4)S1A—C2A—N1A—C1A179.9 (4)
N1—C2—N2—C21178.1 (5)N1A—C2A—N2A—C21A177.6 (5)
S1—C2—N2—C212.3 (8)S1A—C2A—N2A—C21A2.8 (8)
O1—C1—C11—C1687.4 (7)O1A—C1A—C11A—C16A90.3 (7)
N1—C1—C11—C1692.1 (6)N1A—C1A—C11A—C16A91.5 (6)
O1—C1—C11—C1290.6 (7)O1A—C1A—C11A—C12A87.6 (7)
N1—C1—C11—C1289.9 (6)N1A—C1A—C11A—C12A90.7 (6)
C16—C11—C12—C130.1 (8)C16A—C11A—C12A—C13A1.7 (8)
C1—C11—C12—C13178.2 (5)C1A—C11A—C12A—C13A179.7 (5)
C16—C11—C12—Cl1180.0 (4)C16A—C11A—C12A—Cl1A179.0 (4)
C1—C11—C12—Cl11.9 (7)C1A—C11A—C12A—Cl1A1.0 (7)
C11—C12—C13—C141.5 (9)C11A—C12A—C13A—C14A1.1 (9)
Cl1—C12—C13—C14178.3 (5)Cl1A—C12A—C13A—C14A179.6 (5)
C12—C13—C14—C152.1 (10)C12A—C13A—C14A—C15A0.5 (10)
C13—C14—C15—C161.0 (10)C13A—C14A—C15A—C16A0.5 (10)
C12—C11—C16—C151.2 (8)C12A—C11A—C16A—C15A1.7 (8)
C1—C11—C16—C15179.3 (5)C1A—C11A—C16A—C15A179.6 (5)
C12—C11—C16—Cl2178.4 (4)C12A—C11A—C16A—Cl2A179.7 (4)
C1—C11—C16—Cl20.3 (7)C1A—C11A—C16A—Cl2A2.4 (7)
C14—C15—C16—C110.7 (9)C14A—C15A—C16A—C11A1.1 (9)
C14—C15—C16—Cl2178.9 (5)C14A—C15A—C16A—Cl2A179.1 (5)
C2—N2—C21—C22135.7 (5)C2A—N2A—C21A—C22A37.2 (8)
C2—N2—C21—C2647.8 (8)C2A—N2A—C21A—C26A146.3 (5)
C26—C21—C22—C230.0 (8)C26A—C21A—C22A—C23A0.8 (8)
N2—C21—C22—C23176.5 (5)N2A—C21A—C22A—C23A177.2 (5)
C21—C22—C23—C240.3 (8)C21A—C22A—C23A—C24A2.5 (8)
C21—C22—C23—C27177.5 (5)C21A—C22A—C23A—C27A179.1 (5)
C22—C23—C24—C250.7 (9)C22A—C23A—C24A—C25A2.7 (8)
C27—C23—C24—C25177.8 (6)C27A—C23A—C24A—C25A179.3 (5)
C23—C24—C25—C260.8 (10)C23A—C24A—C25A—C26A1.3 (9)
C22—C21—C26—C250.2 (9)C24A—C25A—C26A—C21A0.3 (9)
N2—C21—C26—C25176.3 (5)C22A—C21A—C26A—C25A0.6 (8)
C24—C25—C26—C210.5 (10)N2A—C21A—C26A—C25A176.0 (5)
C24—C23—C27—F219.4 (9)C24A—C23A—C27A—F3A148.0 (6)
C22—C23—C27—F2163.4 (6)C22A—C23A—C27A—F3A35.3 (7)
C24—C23—C27—F3141.1 (6)C24A—C23A—C27A—F2A26.0 (8)
C22—C23—C27—F341.7 (8)C22A—C23A—C27A—F2A157.3 (5)
C24—C23—C27—F1100.5 (7)C24A—C23A—C27A—F1A93.8 (7)
C22—C23—C27—F176.7 (7)C22A—C23A—C27A—F1A82.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1Ai0.882.603.434 (4)159
N2—H2···O10.881.962.670 (5)137
N2—H2···O1Aii0.882.383.115 (6)141
N1A—H1A···S1i0.882.433.305 (4)172
N2A—H2A···O1A0.881.992.709 (6)138
N2A—H2A···O1iii0.882.383.070 (6)136
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y1/2, z+1/2; (iii) x+1, y+1/2, z+1/2.
 

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