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The structure of the title compound, C18H14F4N2O2S, consists of mol­ecules that pack in a linear hydrogen-bonded chain along the c axis. This hydrogen-bonding arrangement involves the hydr­oxy group and one of the sulfonyl O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034501/at6044sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034501/at6044Isup2.hkl
Contains datablock I

CCDC reference: 289635

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.098
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C11 .. 5.01 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C11 ... 1.45 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenylsulfonyl)- 2-hydroxy-2-methylpropionamide top
Crystal data top
C18H14F4N2O4SF(000) = 880.00
Mr = 430.37Dx = 1.554 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybcCell parameters from 14876 reflections
a = 14.882 (5) Åθ = 3.0–27.5°
b = 12.213 (3) ŵ = 0.24 mm1
c = 10.461 (3) ÅT = 296 K
β = 104.680 (13)°Block, colourless
V = 1839.3 (9) Å30.29 × 0.25 × 0.17 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2973 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.027
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1919
Tmin = 0.881, Tmax = 0.959k = 1515
17686 measured reflectionsl = 1311
4206 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[0.0006Fo2 + 1.16σ(Fo2)]/(4Fo2)
wR(F2) = 0.098(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.29 e Å3
4206 reflectionsΔρmin = 0.39 e Å3
262 parameters
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.34160 (3)0.14708 (3)0.80523 (4)0.03962 (11)
F10.31765 (13)0.69861 (11)0.5144 (2)0.1255 (7)
F20.30524 (11)0.79072 (12)0.68145 (16)0.0936 (5)
F30.20991 (12)0.81569 (10)0.49787 (14)0.0887 (4)
F40.65223 (11)0.02895 (12)0.58995 (18)0.0999 (5)
O210.25122 (10)0.18239 (10)0.51043 (12)0.0539 (3)
O220.10729 (12)0.25848 (10)0.71760 (16)0.0699 (4)
O230.33168 (9)0.26421 (9)0.79782 (12)0.0475 (3)
O240.35571 (10)0.09517 (11)0.93268 (11)0.0555 (3)
N310.17082 (11)0.35417 (10)0.57536 (13)0.0440 (4)
N320.10399 (12)0.87647 (12)0.74293 (19)0.0655 (5)
C10.23860 (12)0.08755 (12)0.70465 (16)0.0419 (4)
C20.18791 (12)0.15556 (12)0.58638 (16)0.0421 (4)
C30.10517 (16)0.09143 (17)0.5067 (2)0.0654 (6)
C40.15144 (12)0.26156 (12)0.63461 (17)0.0444 (4)
C50.15184 (12)0.46206 (12)0.60581 (14)0.0396 (4)
C60.07939 (12)0.48993 (13)0.65975 (17)0.0467 (5)
C70.06677 (12)0.59808 (13)0.69100 (18)0.0474 (5)
C80.12512 (12)0.67921 (12)0.66713 (16)0.0432 (4)
C90.19556 (12)0.65150 (12)0.60718 (17)0.0435 (4)
C100.20865 (12)0.54404 (12)0.57679 (17)0.0433 (4)
C110.11321 (13)0.79007 (14)0.7084 (2)0.0495 (5)
C120.25753 (17)0.73792 (16)0.5756 (2)0.0657 (7)
C130.43448 (12)0.11046 (13)0.73879 (16)0.0425 (4)
C140.48534 (14)0.01695 (16)0.7837 (2)0.0574 (5)
C150.55891 (17)0.01021 (18)0.7323 (2)0.0704 (7)
C160.57945 (16)0.05572 (19)0.6399 (2)0.0653 (6)
C170.53069 (14)0.14876 (18)0.5938 (2)0.0635 (6)
C180.45702 (13)0.17684 (14)0.64421 (19)0.0524 (5)
H60.03930.43590.67500.058*
H70.01850.61650.72860.059*
H100.25580.52590.53680.054*
H110.19610.07490.75970.052*
H120.25520.01810.67200.052*
H140.46930.02640.84760.070*
H150.59440.07250.76020.086*
H170.54720.19150.52980.080*
H180.42210.23930.61510.065*
H310.07700.13080.42730.075*
H320.06070.08220.55820.075*
H330.12530.02090.48440.075*
H2110.22410.16660.42440.069*
H3110.20880.34690.52890.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0468 (2)0.0365 (2)0.0393 (2)0.00418 (18)0.01773 (18)0.00016 (17)
F10.1383 (15)0.0606 (8)0.232 (2)0.0169 (8)0.1466 (16)0.0080 (10)
F20.0757 (10)0.0776 (8)0.1223 (12)0.0301 (7)0.0158 (9)0.0040 (8)
F30.1166 (12)0.0561 (7)0.1001 (9)0.0068 (7)0.0398 (9)0.0290 (7)
F40.0755 (10)0.1045 (11)0.1411 (13)0.0075 (8)0.0667 (9)0.0202 (9)
O210.0712 (9)0.0523 (7)0.0472 (6)0.0076 (6)0.0318 (6)0.0051 (5)
O220.0935 (12)0.0459 (7)0.0936 (10)0.0101 (7)0.0669 (9)0.0134 (7)
O230.0569 (8)0.0358 (5)0.0549 (7)0.0069 (5)0.0237 (6)0.0078 (5)
O240.0654 (9)0.0625 (7)0.0414 (6)0.0029 (6)0.0187 (6)0.0097 (5)
N310.0559 (9)0.0360 (6)0.0473 (7)0.0047 (6)0.0262 (6)0.0043 (5)
N320.0626 (11)0.0449 (9)0.0948 (13)0.0037 (8)0.0308 (10)0.0072 (8)
C10.0470 (10)0.0328 (7)0.0486 (9)0.0047 (7)0.0170 (7)0.0010 (6)
C20.0520 (10)0.0348 (7)0.0428 (8)0.0012 (7)0.0179 (7)0.0005 (6)
C30.0708 (15)0.0572 (11)0.0595 (11)0.0072 (10)0.0001 (10)0.0027 (9)
C40.0500 (11)0.0377 (8)0.0496 (9)0.0019 (7)0.0202 (8)0.0050 (7)
C50.0451 (10)0.0359 (7)0.0396 (8)0.0049 (7)0.0138 (7)0.0051 (6)
C60.0471 (11)0.0403 (8)0.0573 (10)0.0004 (7)0.0217 (8)0.0073 (7)
C70.0450 (11)0.0459 (9)0.0569 (10)0.0069 (8)0.0234 (8)0.0036 (8)
C80.0462 (10)0.0370 (8)0.0479 (9)0.0076 (7)0.0148 (7)0.0035 (6)
C90.0456 (10)0.0380 (8)0.0499 (9)0.0017 (7)0.0174 (7)0.0061 (7)
C100.0465 (10)0.0405 (8)0.0486 (9)0.0045 (7)0.0227 (8)0.0051 (7)
C110.0453 (11)0.0432 (9)0.0627 (11)0.0045 (7)0.0186 (9)0.0023 (8)
C120.0701 (16)0.0437 (10)0.0958 (16)0.0053 (10)0.0444 (13)0.0003 (11)
C130.0429 (10)0.0420 (8)0.0443 (8)0.0031 (7)0.0144 (7)0.0015 (7)
C140.0605 (13)0.0485 (10)0.0660 (11)0.0071 (9)0.0213 (10)0.0074 (9)
C150.0635 (14)0.0552 (11)0.0959 (16)0.0158 (10)0.0267 (12)0.0008 (11)
C160.0492 (13)0.0713 (13)0.0830 (14)0.0011 (10)0.0311 (11)0.0198 (11)
C170.0556 (13)0.0723 (13)0.0719 (12)0.0065 (11)0.0336 (10)0.0025 (10)
C180.0527 (11)0.0508 (10)0.0603 (11)0.0006 (8)0.0262 (9)0.0075 (8)
Geometric parameters (Å, º) top
S1—O231.4382 (11)C9—C101.376 (2)
S1—O241.4428 (12)C9—C121.493 (3)
S1—C11.7798 (16)C13—C141.385 (2)
S1—C131.7551 (19)C13—C181.385 (2)
F1—C121.316 (3)C14—C151.377 (3)
F2—C121.322 (2)C15—C161.351 (3)
F3—C121.331 (2)C16—C171.368 (3)
F4—C161.356 (3)C17—C181.375 (3)
O21—C21.416 (2)O21—H2110.909
O22—C41.215 (2)N31—H3110.838
N31—C41.355 (2)C1—H110.970
N31—C51.401 (2)C1—H120.970
N32—C111.135 (2)C3—H310.960
C1—C21.522 (2)C3—H320.960
C2—C31.518 (2)C3—H330.960
C2—C41.538 (2)C6—H60.930
C5—C61.380 (2)C7—H70.930
C5—C101.393 (2)C10—H100.930
C6—C71.385 (2)C14—H140.930
C7—C81.381 (2)C15—H150.930
C8—C91.393 (2)C17—H170.930
C8—C111.446 (2)C18—H180.930
S1···O21i3.4955 (14)C6···H31i3.171
F1···F2ii3.443 (2)C6···H33i3.293
F1···F4iii3.565 (2)C6···H211i3.596
F1···C17iii3.338 (3)C7···H33i3.307
F2···F1iv3.443 (2)C10···H11viii3.582
F2···C17v3.404 (2)C10···H15v3.316
F3···F4iii3.100 (2)C11···H6xi3.349
F3···C7ii3.534 (2)C11···H12xii3.574
F3···C8ii3.370 (2)C11···H31xiii2.988
F3···C11ii3.271 (2)C12···H12xii3.570
F4···F1iii3.565 (2)C12···H17iii3.467
F4···F3iii3.100 (2)C15···H10vii3.203
F4···O21vi3.255 (2)C15···H17vi3.566
F4···O23vii3.4275 (19)C15···H18vii3.429
F4···C10vii3.580 (2)C18···H15v3.368
F4···C18vi3.598 (2)H6···N32ix2.596
O21···S1viii3.4955 (14)H6···C3i3.376
O21···F4vi3.255 (2)H6···C11ix3.349
O21···O22viii3.3418 (18)H6···H31i2.682
O21···O23viii2.856 (2)H6···H33i3.209
O21···O24viii3.3318 (19)H6···H211i3.507
O22···O21i3.3418 (18)H7···F3iv3.560
O22···N32ix3.576 (2)H7···O22xi2.713
O22···C3i3.544 (2)H7···N32ix3.504
O22···C7ix3.566 (2)H7···H11xi3.266
O22···C11ix3.578 (2)H7···H32xi2.806
O23···F4v3.4275 (19)H7···H33i3.218
O23···O21i2.856 (2)H10···O24viii2.531
O23···C15v3.256 (2)H10···N32ii3.530
O24···O21i3.3318 (19)H10···C15v3.203
O24···N31i3.502 (2)H10···H11viii3.067
O24···C10i3.410 (2)H10···H15v2.920
O24···C14x3.566 (2)H11···N31i3.525
O24···C15x3.566 (2)H11···N32xiv2.768
N31···O24viii3.502 (2)H11···C10i3.582
N32···O22xi3.576 (2)H11···H7ix3.266
N32···C1xii3.350 (2)H11···H10i3.067
N32···C3xiii3.542 (2)H11···H211i3.570
N32···C6xi3.437 (2)H11···H311i2.934
N32···C10iv3.579 (2)H12···F2xiv2.870
C1···N32xiv3.350 (2)H12···F3xiv3.043
C3···O22viii3.544 (2)H12···F4vi3.413
C3···N32xiii3.542 (2)H12···N32xiv3.075
C6···N32ix3.437 (2)H12···C11xiv3.574
C6···C6xiii3.579 (2)H12···C12xiv3.570
C7···F3iv3.534 (2)H14···F2xiv3.438
C7···O22xi3.566 (2)H14···O24x3.121
C8···F3iv3.370 (2)H14···H14x3.153
C10···F4v3.580 (2)H14···H18vii3.261
C10···O24viii3.410 (2)H15···O23vii2.428
C10···N32ii3.579 (2)H15···O24x3.121
C10···C15v3.591 (2)H15···N31vii3.595
C11···F3iv3.271 (2)H15···C10vii3.316
C11···O22xi3.578 (2)H15···C18vii3.368
C14···O24x3.566 (2)H15···H10vii2.920
C15···O23vii3.256 (2)H15···H17vi3.538
C15···O24x3.566 (2)H15···H18vii2.684
C15···C10vii3.591 (2)H15···H311vii3.338
C16···C16vi3.535 (3)H17···F1iii2.555
C16···C17vi3.587 (3)H17···F2vii3.472
C17···F1iii3.338 (3)H17···F2iii3.494
C17···F2vii3.404 (2)H17···O23viii3.539
C17···C16vi3.587 (3)H17···C12iii3.467
C18···F4vi3.598 (2)H17···C15vi3.566
S1···H18i3.449H17···H15vi3.538
S1···H211i3.301H18···S1viii3.449
S1···H311i3.425H18···O23viii3.250
F1···H17iii2.555H18···O24viii2.784
F2···H12xii2.870H18···C15v3.429
F2···H14xii3.438H18···H14v3.261
F2···H17v3.472H18···H15v2.684
F2···H17iii3.494H31···O22viii2.709
F3···H7ii3.560H31···N32xiii2.829
F3···H12xii3.043H31···C6viii3.171
F3···H33xii2.792H31···C11xiii2.988
F4···H12vi3.413H31···H6viii2.682
F4···H211vi3.042H31···H32xv3.339
O22···H7ix2.713H32···N32xiv3.135
O22···H31i2.709H32···N32xiii3.503
O22···H211i2.575H32···C3xv3.193
O22···H311i3.471H32···H7ix2.806
O23···H15v2.428H32···H31xv3.339
O23···H17i3.539H32···H32xv2.767
O23···H18i3.250H32···H33xv2.970
O23···H211i2.471H33···F3xiv2.792
O24···H10i2.531H33···N32xiv3.311
O24···H14x3.121H33···C6viii3.293
O24···H15x3.121H33···C7viii3.307
O24···H18i2.784H33···H6viii3.209
O24···H211i3.497H33···H7viii3.218
O24···H311i2.723H33···H32xv2.970
N31···H11viii3.525H211···S1viii3.301
N31···H15v3.595H211···F4vi3.042
N31···H211i3.544H211···O22viii2.575
N32···H6xi2.596H211···O23viii2.471
N32···H7xi3.504H211···O24viii3.497
N32···H10iv3.530H211···N31viii3.544
N32···H11xii2.768H211···C4viii3.077
N32···H12xii3.075H211···C5viii3.594
N32···H31xiii2.829H211···C6viii3.596
N32···H32xii3.135H211···H6viii3.507
N32···H32xiii3.503H211···H11viii3.570
N32···H33xii3.311H311···S1viii3.425
C3···H6viii3.376H311···O22viii3.471
C3···H32xv3.193H311···O24viii2.723
C4···H211i3.077H311···H11viii2.934
C5···H211i3.594H311···H15v3.338
O23—S1—O24118.41 (7)S1—C13—C18119.44 (13)
O23—S1—C1108.25 (7)C14—C13—C18120.97 (19)
O23—S1—C13108.21 (8)C13—C14—C15119.1 (2)
O24—S1—C1105.58 (8)C14—C15—C16118.8 (2)
O24—S1—C13108.01 (8)F4—C16—C15118.6 (2)
C1—S1—C13107.97 (8)F4—C16—C17117.9 (2)
C4—N31—C5127.03 (16)C15—C16—C17123.4 (2)
S1—C1—C2115.64 (11)C16—C17—C18118.4 (2)
O21—C2—C1108.61 (14)C13—C18—C17119.29 (17)
O21—C2—C3111.96 (15)C2—O21—H211108.3
O21—C2—C4109.25 (13)C4—N31—H311115.4
C1—C2—C3109.30 (14)C5—N31—H311115.8
C1—C2—C4109.65 (13)S1—C1—H11107.9
C3—C2—C4108.05 (15)S1—C1—H12107.9
O22—C4—N31124.67 (16)C2—C1—H11107.8
O22—C4—C2120.55 (15)C2—C1—H12108.0
N31—C4—C2114.76 (16)H11—C1—H12109.5
N31—C5—C6123.25 (16)C2—C3—H31109.4
N31—C5—C10117.26 (17)C2—C3—H32109.4
C6—C5—C10119.48 (15)C2—C3—H33109.6
C5—C6—C7119.90 (17)H31—C3—H32109.5
C6—C7—C8120.83 (19)H31—C3—H33109.5
C7—C8—C9119.11 (15)H32—C3—H33109.5
C7—C8—C11119.19 (18)C5—C6—H6119.8
C9—C8—C11121.68 (17)C7—C6—H6120.3
C8—C9—C10120.17 (17)C6—C7—H7119.7
C8—C9—C12120.38 (16)C8—C7—H7119.4
C10—C9—C12119.45 (19)C5—C10—H10119.7
C5—C10—C9120.41 (18)C9—C10—H10119.9
N32—C11—C8178.8 (2)C13—C14—H14119.7
F1—C12—F2107.4 (2)C15—C14—H14121.2
F1—C12—F3106.6 (2)C14—C15—H15121.2
F1—C12—C9112.60 (16)C16—C15—H15120.0
F2—C12—F3104.66 (16)C16—C17—H17120.4
F2—C12—C9112.9 (2)C18—C17—H17121.2
F3—C12—C9112.12 (18)C13—C18—H18119.9
S1—C13—C14119.58 (15)C17—C18—H18120.8
O23—S1—C1—C229.50 (16)C5—C6—C7—C80.9 (2)
O23—S1—C13—C14151.24 (13)C6—C7—C8—C92.0 (2)
O23—S1—C13—C1827.41 (15)C6—C7—C8—C11176.30 (15)
O24—S1—C1—C2157.24 (13)C7—C8—C9—C102.4 (2)
O24—S1—C13—C1421.92 (16)C7—C8—C9—C12177.74 (16)
O24—S1—C13—C18156.73 (13)C11—C8—C9—C10175.85 (15)
C1—S1—C13—C1491.81 (14)C11—C8—C9—C124.1 (2)
C1—S1—C13—C1889.55 (14)C8—C9—C10—C50.1 (2)
C13—S1—C1—C287.43 (15)C8—C9—C12—F1177.35 (17)
C4—N31—C5—C627.9 (2)C8—C9—C12—F260.8 (2)
C4—N31—C5—C10153.49 (16)C8—C9—C12—F357.1 (2)
C5—N31—C4—O226.2 (2)C10—C9—C12—F12.7 (2)
C5—N31—C4—C2175.33 (14)C10—C9—C12—F2119.08 (19)
S1—C1—C2—O2154.45 (16)C10—C9—C12—F3122.97 (19)
S1—C1—C2—C3176.87 (14)C12—C9—C10—C5179.79 (16)
S1—C1—C2—C464.86 (19)S1—C13—C14—C15179.08 (15)
O21—C2—C4—O22168.83 (15)S1—C13—C18—C17179.05 (14)
O21—C2—C4—N3112.63 (18)C14—C13—C18—C170.4 (2)
C1—C2—C4—O2249.9 (2)C18—C13—C14—C150.5 (2)
C1—C2—C4—N31131.55 (15)C13—C14—C15—C160.3 (3)
C3—C2—C4—O2269.1 (2)C14—C15—C16—F4179.69 (19)
C3—C2—C4—N31109.40 (17)C14—C15—C16—C170.1 (3)
N31—C5—C6—C7177.98 (14)F4—C16—C17—C18179.72 (18)
N31—C5—C10—C9178.30 (14)C15—C16—C17—C180.1 (3)
C6—C5—C10—C93.0 (2)C16—C17—C18—C130.2 (2)
C10—C5—C6—C73.4 (2)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+3/2, z1/2; (iii) x+1, y+1, z+1; (iv) x, y+3/2, z+1/2; (v) x+1, y+1/2, z+3/2; (vi) x+1, y, z+1; (vii) x+1, y1/2, z+3/2; (viii) x, y+1/2, z1/2; (ix) x, y1/2, z+3/2; (x) x+1, y, z+2; (xi) x, y+1/2, z+3/2; (xii) x, y+1, z; (xiii) x, y+1, z+1; (xiv) x, y1, z; (xv) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O21—H211···O23viii0.912.472.856 (2)106
Symmetry code: (viii) x, y+1/2, z1/2.
 

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