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In the title compound, C10H11F3N2O, the dihedral angle between the di­methyl­urea and phenyl group planes is 37.49 (7)°. In the crystal, mol­ecules are linked by N—H...O hydrogen bonds, generating chains propagating in the [010] direction. The tri­fluoro­methyl group is disordered over two orientations in a 0.577 (12):0.423 (12) ratio.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314618000408/hb4201sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314618000408/hb4201Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314618000408/hb4201Isup3.cml
Supplementary material

CCDC reference: 1815173

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.044
  • wR factor = 0.139
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.082 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 4 Report
Alert level G PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 5 Report PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records 1 Report PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT242_ALERT_2_G Low 'MainMol' Ueq as Compared to Neighbors of C1 Check PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 19% Note PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 60 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 33 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 11 ALERT level G = General information/check it is not something unexpected 2 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 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

1,1-Dimethyl-3-[4-(trifluoromethyl)phenyl]urea top
Crystal data top
C10H11F3N2ODx = 1.385 Mg m3
Mr = 232.21Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, PbcaCell parameters from 2946 reflections
a = 9.8152 (3) Åθ = 3.9–73.8°
b = 10.0783 (2) ŵ = 1.10 mm1
c = 22.5120 (7) ÅT = 293 K
V = 2226.90 (11) Å3Block, colourless
Z = 80.30 × 0.23 × 0.10 mm
F(000) = 960
Data collection top
Agilent SuperNova, Dual, Cu at zero, Atlas
diffractometer
1708 reflections with I > 2σ(I)
ω scansRint = 0.030
Absorption correction: gaussian
(CrysAlis PRO; Agilent, 2014)
θmax = 74.0°, θmin = 3.9°
Tmin = 0.940, Tmax = 0.974h = 117
7168 measured reflectionsk = 1210
2217 independent reflectionsl = 2825
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0878P)2 + 0.0492P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.139(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.16 e Å3
2217 reflectionsΔρmin = 0.17 e Å3
176 parametersExtinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
60 restraintsExtinction coefficient: 0.0102 (9)
Special details top

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. All hydrogen atoms were placed in calculated positions and refined using a riding model. Methyl C—H bonds were fixed at 0.96 Å, with displacement parameters 1.5 times Ueq(C), and were allowed to spin about the C—N bond. The N—H bond was fixed at 0.86 Å and aromatic C—H distances were set to 0.93 Å and their U(iso) set to 1.2 times the Ueq for the atoms to which they are bonded.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.5872 (3)0.0387 (3)0.72719 (10)0.1049 (8)
C20.49935 (19)0.02575 (19)0.67302 (8)0.0730 (5)
C30.5321 (2)0.06604 (19)0.62979 (9)0.0800 (5)
H30.60700.12140.63490.096*
C40.45445 (17)0.07598 (15)0.57921 (8)0.0678 (4)
H40.47740.13780.55020.081*
C50.34195 (14)0.00549 (12)0.57108 (6)0.0517 (3)
C60.30912 (16)0.09806 (14)0.61453 (7)0.0613 (4)
H60.23410.15330.60960.074*
C70.38819 (18)0.10778 (17)0.66514 (7)0.0707 (5)
H70.36640.17010.69410.085*
C80.20108 (14)0.08594 (11)0.48853 (6)0.0517 (3)
C90.0580 (2)0.15002 (18)0.40623 (10)0.0831 (5)
H9A0.05210.23040.42900.125*
H9B0.03200.11990.39640.125*
H9C0.10820.16650.37040.125*
C100.1105 (2)0.08604 (16)0.42132 (9)0.0778 (5)
H10A0.19220.11510.40190.117*
H10B0.03540.09120.39410.117*
H10C0.09280.14180.45500.117*
N10.26294 (13)0.01353 (10)0.51968 (5)0.0546 (3)
H10.25290.09340.50700.065*
N20.12717 (14)0.04922 (11)0.44086 (6)0.0622 (4)
O10.21290 (14)0.20262 (9)0.50340 (5)0.0728 (4)
F10.7132 (6)0.024 (2)0.7171 (3)0.169 (5)0.423 (12)
F20.5686 (15)0.1449 (10)0.7571 (5)0.170 (5)0.423 (12)
F30.5525 (14)0.0492 (11)0.7660 (4)0.164 (4)0.423 (12)
F1A0.6752 (9)0.1385 (8)0.7205 (3)0.148 (3)0.577 (12)
F3A0.6621 (13)0.0643 (6)0.7389 (4)0.179 (4)0.577 (12)
F2A0.5211 (7)0.0711 (18)0.7739 (2)0.206 (6)0.577 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.108 (2)0.137 (2)0.0695 (13)0.0207 (16)0.0197 (12)0.0095 (13)
C20.0724 (11)0.0874 (10)0.0592 (9)0.0186 (8)0.0063 (7)0.0109 (7)
C30.0773 (11)0.0784 (10)0.0841 (12)0.0059 (8)0.0200 (9)0.0042 (8)
C40.0750 (10)0.0551 (7)0.0734 (10)0.0061 (6)0.0107 (8)0.0048 (6)
C50.0568 (8)0.0428 (5)0.0554 (7)0.0081 (5)0.0007 (6)0.0026 (5)
C60.0601 (9)0.0642 (8)0.0597 (8)0.0048 (6)0.0068 (6)0.0068 (6)
C70.0772 (11)0.0825 (10)0.0523 (8)0.0172 (8)0.0104 (7)0.0088 (7)
C80.0574 (8)0.0389 (5)0.0587 (7)0.0017 (5)0.0043 (6)0.0007 (5)
C90.0924 (13)0.0718 (10)0.0850 (12)0.0069 (8)0.0206 (10)0.0156 (8)
C100.0931 (13)0.0589 (8)0.0814 (11)0.0074 (7)0.0245 (9)0.0080 (7)
N10.0669 (7)0.0348 (5)0.0620 (7)0.0007 (4)0.0077 (5)0.0041 (4)
N20.0704 (8)0.0499 (6)0.0664 (7)0.0012 (5)0.0119 (6)0.0021 (5)
O10.1053 (10)0.0351 (5)0.0781 (7)0.0012 (4)0.0095 (6)0.0024 (4)
F10.086 (3)0.322 (15)0.099 (4)0.005 (5)0.029 (2)0.024 (6)
F20.213 (12)0.172 (6)0.124 (7)0.007 (5)0.083 (8)0.061 (5)
F30.203 (9)0.210 (7)0.078 (4)0.017 (6)0.043 (4)0.056 (4)
F1A0.148 (5)0.178 (5)0.116 (4)0.073 (4)0.067 (3)0.023 (3)
F3A0.217 (8)0.168 (4)0.152 (6)0.037 (5)0.117 (6)0.009 (3)
F2A0.140 (4)0.421 (18)0.0560 (18)0.029 (8)0.0078 (18)0.026 (5)
Geometric parameters (Å, º) top
C1—F11.267 (6)C6—C71.382 (2)
C1—F21.277 (7)C6—H60.9300
C1—F2A1.277 (7)C7—H70.9300
C1—F31.290 (7)C8—O11.2281 (16)
C1—F3A1.300 (6)C8—N21.3471 (19)
C1—F1A1.334 (5)C8—N11.3658 (17)
C1—C21.499 (3)C9—N21.449 (2)
C2—C71.380 (3)C9—H9A0.9600
C2—C31.381 (3)C9—H9B0.9600
C3—C41.374 (3)C9—H9C0.9600
C3—H30.9300C10—N21.4417 (19)
C4—C51.388 (2)C10—H10A0.9600
C4—H40.9300C10—H10B0.9600
C5—C61.390 (2)C10—H10C0.9600
C5—N11.4060 (18)N1—H10.8600
F1—C1—F2109.5 (6)C5—C6—H6120.1
F1—C1—F3107.3 (7)C2—C7—C6120.49 (16)
F2—C1—F3100.4 (6)C2—C7—H7119.8
F2A—C1—F3A108.9 (6)C6—C7—H7119.8
F2A—C1—F1A103.3 (6)O1—C8—N2122.07 (12)
F3A—C1—F1A105.0 (5)O1—C8—N1121.39 (13)
F1—C1—C2113.9 (3)N2—C8—N1116.54 (11)
F2—C1—C2114.9 (4)N2—C9—H9A109.5
F2A—C1—C2113.6 (4)N2—C9—H9B109.5
F3—C1—C2109.8 (4)H9A—C9—H9B109.5
F3A—C1—C2114.9 (3)N2—C9—H9C109.5
F1A—C1—C2110.3 (2)H9A—C9—H9C109.5
C7—C2—C3119.65 (16)H9B—C9—H9C109.5
C7—C2—C1120.4 (2)N2—C10—H10A109.5
C3—C2—C1119.9 (2)N2—C10—H10B109.5
C4—C3—C2120.26 (17)H10A—C10—H10B109.5
C4—C3—H3119.9N2—C10—H10C109.5
C2—C3—H3119.9H10A—C10—H10C109.5
C3—C4—C5120.50 (16)H10B—C10—H10C109.5
C3—C4—H4119.8C8—N1—C5124.59 (10)
C5—C4—H4119.8C8—N1—H1117.7
C4—C5—C6119.25 (14)C5—N1—H1117.7
C4—C5—N1117.81 (13)C8—N2—C10124.32 (12)
C6—C5—N1122.89 (13)C8—N2—C9119.22 (13)
C7—C6—C5119.85 (15)C10—N2—C9116.46 (14)
C7—C6—H6120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.082.8939 (13)157
Symmetry code: (i) x+1/2, y1/2, z.
 

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