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The process of the first-order solid-to-solid phase transition of 1-ethyl-3-(4-methylpentanoyl)urea (1) was observed by means of a detailed temperature-resolved single-crystal diffraction method, which resembles watching a series of stop-motion photographs. The transition consists of two elementary processes, one supramolecular and the other molecular. Crystal structures from before and after the phase transition are isostructural. The straight-ribbon-like one-dimensional hydrogen-bonding structure is formed and stacked to form a molecular layer. The geometry of the layer is retained during the phase transition. The relative position of the layer with its neighbours, on the other hand, changes gradually with increasing temperature. The change is accelerated at the temperature representing the start of the endotherm seen in the DSC curves of (1). The structural variation yields void space between the neighbouring layers. When the void space grows enough that the crystal is unstable, the 3-methylbutyl group on the last of the molecules turns into a disordered structure with drastic conformational changes to fill up the void space. The phase transition process is well supported with simple force-field calculations. A crystal of 1-(4-methylpentanoyl)-3-propylurea (2), which shows no solid-to-solid phase transitions, was also analysed by the same method for comparison.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768103005792/lc0061sup1.cif
Contains datablocks global, ethyl98K, ethyl298K, ethyl328K, ethyl348K, ethyl350K, ethyl352K, ethyl354K, ethyl356K, ethyl358K, ethyl360K, ethyl362K, ethyl364K, ethyl366K, ethyl368K, ethyl370K, ethyl372K, ethyl374K, propyl98K, propyl298K, propyl348K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl98Ksup2.hkl
Contains datablock ethyl98K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl298Ksup3.hkl
Contains datablock ethyl298K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl328Ksup4.hkl
Contains datablock ethyl328K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl348Ksup5.hkl
Contains datablock ethyl348K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl350Ksup6.hkl
Contains datablock ethyl350K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl352Ksup7.hkl
Contains datablock ethyl352K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl354Ksup8.hkl
Contains datablock ethyl354K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl356Ksup9.hkl
Contains datablock ethyl356K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl358Ksup10.hkl
Contains datablock ethyl358K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl360Ksup11.hkl
Contains datablock ethyl360K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl362Ksup12.hkl
Contains datablock ethyl362K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl364Ksup13.hkl
Contains datablock ethyl364K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl366Ksup14.hkl
Contains datablock ethyl366K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl368Ksup15.hkl
Contains datablock ethyl368K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl370Ksup16.hkl
Contains datablock ethyl370K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl372Ksup17.hkl
Contains datablock ethyl372K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl374Ksup18.hkl
Contains datablock ethyl374K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061propyl98Ksup19.hkl
Contains datablock propyl98K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061propyl298Ksup20.hkl
Contains datablock propyl298K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061propyl348Ksup21.hkl
Contains datablock propyl348K

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768103005792/lc0061sup22.pdf
Supplementary material

CCDC references: 219252; 219253; 219254; 219255; 219256; 219257; 219258; 219259; 219260; 219261; 219262; 219263; 219264; 219265; 219266; 219267; 219268; 219269; 219270; 219271

Computing details top

For all compounds, data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO (Rigaku Corporation, 1998); data reduction: PROCESS-AUTO (Rigaku Corporation, 1998). Program(s) used to solve structure: SIR97 (Sheldrick, 1990) for ethyl98K, propyl98K; The final structure at 98K was used as an initial model. for ethyl298K, propyl298K; The final structure at 298K was used as an initial model. for ethyl328K, propyl348K; The final structure at 328K was used as an initial model. for ethyl348K; The final structure at 348K was used as an initial model. for ethyl350K; The final structure at 350K was used as an initial model. for ethyl352K; The final structure at 352K was used as an initial model. for ethyl354K; The final structure at 354K was used as an initial model. for ethyl356K; The final structure at 356K was used as an initial model. for ethyl358K; The final structure at 358K was used as an initial model. for ethyl360K; The final structure at 360K was used as an initial model. for ethyl362K; The final structure at 362K was used as an initial model. for ethyl364K; The final structure at 364K was used as an initial model. for ethyl366K; The final structure at 366K was used as an initial model. for ethyl368K; The final structure at 368K was used as an initial model. The minor part of the disordered 3-methylbutyl group was deleted to avoid some viases for disorder analysis. for ethyl370K; The final structure at 370K was used as an initial model. The minor part of the disordered 3-methylbutyl group was deleted to avoid some viases for disorder analysis. for ethyl372K; The final structure at 372K was used as an initial model. The minor part of the disordered 3-methylbutyl group was deleted to avoid some viases for disorder analysis. for ethyl374K. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-III (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(ethyl98K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.172 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.7038 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.204 (3) ÅCell parameters from 4199 reflections
c = 4.9747 (10) Åθ = 2.3–27.5°
α = 93.021 (11)°µ = 0.08 mm1
β = 90.616 (7)°T = 98 K
γ = 90.319 (10)°Plate, colourless
V = 527.64 (19) Å30.80 × 0.40 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1992 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1011
Oscillation method scansk = 1515
6068 measured reflectionsl = 66
2076 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: difference Fourier map
wR(F2) = 0.128All H-atom parameters refined
S = 1.10 w = 1/[σ2(Fo2) + (0.0769P)2 + 0.1768P]
where P = (Fo2 + 2Fc2)/3
2076 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

Experimental. The crystal is being low temperature phase.

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
O10.44032 (10)0.57459 (7)0.24164 (18)0.0197 (2)
O20.02166 (10)0.40706 (7)0.22035 (18)0.0195 (2)
N10.19696 (12)0.53547 (8)0.3825 (2)0.0165 (3)
H110.128 (2)0.5538 (14)0.506 (4)0.021 (4)*
N20.25049 (12)0.41607 (8)0.0069 (2)0.0167 (2)
H210.338 (2)0.4465 (14)0.003 (4)0.023 (4)*
C10.33545 (14)0.59050 (9)0.4018 (2)0.0158 (3)
C20.15101 (14)0.44889 (9)0.1958 (2)0.0162 (3)
C110.35090 (15)0.67433 (10)0.6398 (2)0.0178 (3)
H1110.439 (2)0.6487 (13)0.745 (3)0.021 (4)*
H1120.2602 (19)0.6735 (13)0.748 (3)0.018 (4)*
C120.38521 (15)0.79070 (10)0.5489 (3)0.0198 (3)
H1210.405 (2)0.8406 (15)0.712 (4)0.027 (4)*
H1220.4770 (19)0.7875 (13)0.445 (3)0.018 (4)*
C130.25484 (18)0.84117 (10)0.3886 (3)0.0260 (3)
H1310.232 (2)0.7902 (16)0.225 (4)0.033 (5)*
C140.3084 (3)0.95237 (12)0.2891 (3)0.0387 (4)
H1410.332 (2)1.0040 (17)0.440 (4)0.040 (5)*
H1420.397 (3)0.9434 (18)0.175 (5)0.047 (6)*
H1430.224 (3)0.9838 (19)0.185 (5)0.053 (6)*
C150.10882 (18)0.85613 (13)0.5535 (4)0.0354 (4)
H1510.131 (2)0.9070 (17)0.722 (4)0.041 (5)*
H1520.065 (3)0.7830 (19)0.622 (5)0.050 (6)*
H1530.026 (3)0.8914 (19)0.445 (5)0.052 (6)*
C210.21377 (14)0.32246 (10)0.1823 (2)0.0181 (3)
H2110.2767 (18)0.3308 (13)0.340 (3)0.017 (4)*
H2120.107 (2)0.3260 (13)0.231 (3)0.019 (4)*
C220.24513 (17)0.21233 (11)0.0605 (3)0.0252 (3)
H2210.355 (2)0.2097 (16)0.005 (4)0.039 (5)*
H2220.179 (2)0.2045 (15)0.100 (4)0.033 (5)*
H2230.221 (2)0.1502 (16)0.196 (4)0.037 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0159 (4)0.0238 (5)0.0191 (4)0.0018 (3)0.0033 (4)0.0007 (3)
O20.0150 (4)0.0237 (5)0.0195 (4)0.0031 (3)0.0032 (3)0.0011 (3)
N10.0139 (5)0.0198 (5)0.0155 (5)0.0004 (4)0.0037 (4)0.0015 (4)
N20.0136 (5)0.0197 (5)0.0164 (5)0.0017 (4)0.0012 (4)0.0018 (4)
C10.0158 (6)0.0165 (5)0.0154 (6)0.0006 (4)0.0010 (5)0.0030 (4)
C20.0165 (6)0.0171 (5)0.0151 (5)0.0006 (4)0.0008 (4)0.0024 (4)
C110.0169 (6)0.0210 (6)0.0153 (6)0.0003 (4)0.0001 (5)0.0010 (4)
C120.0192 (6)0.0196 (6)0.0204 (6)0.0026 (4)0.0016 (5)0.0018 (4)
C130.0374 (8)0.0186 (6)0.0215 (6)0.0000 (5)0.0086 (6)0.0014 (5)
C140.0656 (12)0.0217 (7)0.0289 (8)0.0009 (7)0.0022 (8)0.0029 (6)
C150.0244 (7)0.0270 (7)0.0544 (10)0.0034 (5)0.0106 (7)0.0002 (7)
C210.0170 (6)0.0214 (6)0.0156 (6)0.0004 (4)0.0001 (5)0.0030 (4)
C220.0274 (7)0.0213 (6)0.0267 (7)0.0014 (5)0.0014 (6)0.0010 (5)
Geometric parameters (Å, º) top
O1—C11.2275 (15)C13—C151.527 (2)
O2—C21.2435 (15)C13—C141.540 (2)
N1—C11.3766 (15)C13—H1311.01 (2)
N1—C21.4224 (15)C14—H1410.98 (2)
N1—H110.880 (19)C14—H1420.97 (2)
N2—C21.3321 (16)C14—H1430.99 (2)
N2—C211.4730 (15)C15—H1511.03 (2)
N2—H210.846 (18)C15—H1521.04 (2)
C1—C111.5280 (16)C15—H1531.01 (3)
C11—C121.5417 (17)C21—C221.5280 (18)
C11—H1110.984 (18)C21—H2110.971 (16)
C11—H1120.961 (17)C21—H2120.959 (17)
C12—C131.5304 (19)C22—H2210.99 (2)
C12—H1211.003 (18)C22—H2220.997 (19)
C12—H1220.955 (17)C22—H2231.01 (2)
C1—N1—C2128.59 (10)C15—C13—H131109.2 (11)
C1—N1—H11116.4 (11)C12—C13—H131107.8 (11)
C2—N1—H11114.9 (11)C14—C13—H131108.1 (11)
C2—N2—C21120.62 (11)C13—C14—H141110.9 (12)
C2—N2—H21119.6 (12)C13—C14—H142110.9 (13)
C21—N2—H21119.6 (12)H141—C14—H142109.8 (18)
O1—C1—N1123.40 (11)C13—C14—H143108.6 (13)
O1—C1—C11121.49 (11)H141—C14—H143107.5 (18)
N1—C1—C11115.11 (10)H142—C14—H143109.1 (19)
O2—C2—N2123.75 (11)C13—C15—H151109.7 (11)
O2—C2—N1118.33 (11)C13—C15—H152113.7 (13)
N2—C2—N1117.90 (11)H151—C15—H152106.7 (17)
C1—C11—C12112.12 (10)C13—C15—H153110.8 (13)
C1—C11—H111104.6 (10)H151—C15—H153107.7 (18)
C12—C11—H111109.3 (9)H152—C15—H153108.0 (18)
C1—C11—H112110.2 (10)N2—C21—C22112.23 (10)
C12—C11—H112111.1 (10)N2—C21—H211106.7 (9)
H111—C11—H112109.3 (14)C22—C21—H211110.5 (9)
C13—C12—C11114.44 (11)N2—C21—H212108.5 (10)
C13—C12—H121107.3 (10)C22—C21—H212109.0 (10)
C11—C12—H121108.8 (10)H211—C21—H212109.9 (14)
C13—C12—H122110.3 (10)C21—C22—H221108.9 (12)
C11—C12—H122107.9 (9)C21—C22—H222109.5 (11)
H121—C12—H122107.8 (14)H221—C22—H222109.7 (17)
C15—C13—C12112.30 (12)C21—C22—H223110.3 (12)
C15—C13—C14110.07 (13)H221—C22—H223109.7 (17)
C12—C13—C14109.30 (13)H222—C22—H223108.7 (15)
C2—N1—C1—O14.1 (2)O1—C1—C11—C1258.34 (15)
C2—N1—C1—C11175.84 (11)N1—C1—C11—C12121.68 (12)
C21—N2—C2—O22.54 (18)C1—C11—C12—C1365.93 (14)
C21—N2—C2—N1176.29 (10)C11—C12—C13—C1562.45 (15)
C1—N1—C2—O2177.05 (11)C11—C12—C13—C14175.11 (12)
C1—N1—C2—N21.85 (19)C2—N2—C21—C2281.62 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.846 (18)2.300 (18)2.9778 (15)137.4 (16)
N1—H11···O2ii0.880 (19)1.942 (19)2.8222 (14)179.3 (17)
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl298K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.109 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.8173 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.4339 (12) ÅCell parameters from 3690 reflections
c = 5.0963 (1) Åθ = 2.3–27.5°
α = 92.912 (12)°µ = 0.08 mm1
β = 89.876 (3)°T = 298 K
γ = 90.152 (10)°Plate, colourless
V = 558.00 (6) Å30.80 × 0.40 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
2041 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
6494 measured reflectionsl = 66
2292 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: difference Fourier map
wR(F2) = 0.171H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0925P)2 + 0.1104P]
where P = (Fo2 + 2Fc2)/3
2292 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.43498 (13)0.57527 (10)0.2374 (2)0.0566 (3)
O20.02574 (12)0.40870 (10)0.2301 (2)0.0559 (3)
N10.19711 (14)0.53487 (11)0.3806 (3)0.0458 (3)
H110.13030.55460.49640.055*
N20.25183 (14)0.41611 (11)0.0194 (3)0.0467 (3)
H210.33770.44860.00810.056*
C10.33136 (17)0.59074 (12)0.3945 (3)0.0434 (3)
C20.15267 (17)0.44949 (12)0.2036 (3)0.0435 (3)
C110.34433 (19)0.67384 (13)0.6232 (3)0.0506 (4)
H1110.42350.65180.74070.061*
H1120.24970.67560.72060.061*
C120.3802 (2)0.78742 (14)0.5365 (4)0.0593 (5)
H1220.47210.78450.43140.071*
H1210.40030.83370.69170.071*
C130.2540 (3)0.83858 (16)0.3773 (4)0.0796 (7)
H1310.23170.79050.22370.096*
C140.3089 (5)0.9478 (2)0.2795 (6)0.1270 (14)
H1420.40100.93740.18070.152*
H1410.32730.99700.42760.152*
H1430.23260.97700.16960.152*
C150.1085 (3)0.8545 (2)0.5371 (8)0.1137 (11)
H1520.07520.78650.59750.136*
H1530.03130.88370.42890.136*
H1510.12750.90340.68530.136*
C210.21680 (19)0.32495 (14)0.1641 (3)0.0521 (4)
H2110.27690.33090.32240.062*
H2120.11070.32810.21300.062*
C220.2482 (3)0.21723 (17)0.0493 (5)0.0752 (6)
H2230.22330.16030.17640.090*
H2220.18750.21020.10560.090*
H2210.35360.21290.00450.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0431 (6)0.0655 (7)0.0603 (7)0.0078 (5)0.0161 (5)0.0055 (5)
O20.0417 (6)0.0639 (7)0.0611 (7)0.0104 (5)0.0151 (5)0.0057 (5)
N10.0388 (6)0.0504 (7)0.0478 (7)0.0021 (5)0.0119 (5)0.0017 (5)
N20.0373 (6)0.0524 (7)0.0500 (7)0.0035 (5)0.0094 (5)0.0028 (5)
C10.0393 (7)0.0459 (7)0.0454 (7)0.0009 (6)0.0040 (6)0.0075 (6)
C20.0375 (7)0.0473 (8)0.0459 (8)0.0003 (5)0.0075 (6)0.0044 (6)
C110.0484 (8)0.0565 (9)0.0464 (8)0.0022 (7)0.0016 (7)0.0007 (7)
C120.0574 (10)0.0546 (9)0.0648 (10)0.0081 (7)0.0072 (8)0.0070 (8)
C130.1154 (19)0.0504 (10)0.0725 (13)0.0025 (11)0.0222 (13)0.0023 (9)
C140.222 (4)0.0612 (14)0.099 (2)0.0031 (19)0.000 (2)0.0182 (14)
C150.0764 (17)0.0853 (18)0.179 (3)0.0166 (13)0.027 (2)0.0036 (19)
C210.0456 (8)0.0586 (9)0.0512 (9)0.0001 (7)0.0038 (7)0.0056 (7)
C220.0866 (15)0.0569 (11)0.0815 (14)0.0030 (10)0.0070 (12)0.0040 (9)
Geometric parameters (Å, º) top
O1—C11.2227 (19)C13—C151.526 (4)
O2—C21.2375 (18)C13—C141.547 (3)
N1—C11.3710 (19)C13—H1310.9800
N1—C21.413 (2)C14—H1420.9600
N1—H110.8600C14—H1410.9600
N2—C21.3328 (19)C14—H1430.9600
N2—C211.465 (2)C15—H1520.9600
N2—H210.8600C15—H1530.9600
C1—C111.522 (2)C15—H1510.9600
C11—C121.533 (2)C21—C221.515 (3)
C11—H1110.9700C21—H2110.9700
C11—H1120.9700C21—H2120.9700
C12—C131.537 (3)C22—H2230.9600
C12—H1220.9700C22—H2220.9600
C12—H1210.9700C22—H2210.9600
C1—N1—C2129.32 (13)C15—C13—H131108.4
C1—N1—H11115.3C12—C13—H131108.4
C2—N1—H11115.3C14—C13—H131108.4
C2—N2—C21121.00 (13)C13—C14—H142109.5
C2—N2—H21119.5C13—C14—H141109.5
C21—N2—H21119.5H142—C14—H141109.5
O1—C1—N1123.17 (15)C13—C14—H143109.5
O1—C1—C11121.57 (14)H142—C14—H143109.5
N1—C1—C11115.25 (13)H141—C14—H143109.5
O2—C2—N2123.65 (15)C13—C15—H152109.5
O2—C2—N1118.60 (13)C13—C15—H153109.5
N2—C2—N1117.74 (13)H152—C15—H153109.5
C1—C11—C12113.22 (13)C13—C15—H151109.5
C1—C11—H111108.9H152—C15—H151109.5
C12—C11—H111108.9H153—C15—H151109.5
C1—C11—H112108.9N2—C21—C22112.64 (15)
C12—C11—H112108.9N2—C21—H211109.1
H111—C11—H112107.7C22—C21—H211109.1
C11—C12—C13114.62 (16)N2—C21—H212109.1
C11—C12—H122108.6C22—C21—H212109.1
C13—C12—H122108.6H211—C21—H212107.8
C11—C12—H121108.6C21—C22—H223109.5
C13—C12—H121108.6C21—C22—H222109.5
H122—C12—H121107.6H223—C22—H222109.5
C15—C13—C12112.0 (2)C21—C22—H221109.5
C15—C13—C14109.9 (2)H223—C22—H221109.5
C12—C13—C14109.8 (2)H222—C22—H221109.5
C2—N1—C1—O13.1 (3)O1—C1—C11—C1256.7 (2)
C2—N1—C1—C11176.24 (14)N1—C1—C11—C12123.93 (15)
C21—N2—C2—O21.4 (2)C1—C11—C12—C1366.0 (2)
C21—N2—C2—N1177.30 (13)C11—C12—C13—C1562.9 (2)
C1—N1—C2—O2178.47 (14)C11—C12—C13—C14174.74 (19)
C1—N1—C2—N20.3 (2)C2—N2—C21—C2282.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.373.0573 (17)137
N1—H11···O2ii0.861.992.8525 (17)177
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl328K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.114 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.7817 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.381 (2) ÅCell parameters from 3475 reflections
c = 5.1113 (11) Åθ = 2.3–27.5°
α = 92.491 (8)°µ = 0.08 mm1
β = 90.164 (9)°T = 328 K
γ = 89.589 (9)°Plate, colourless
V = 555.17 (19) Å30.80 × 0.40 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1728 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1516
7578 measured reflectionsl = 66
2169 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0661P)2 + 0.1725P]
where P = (Fo2 + 2Fc2)/3
2169 reflections(Δ/σ)max < 0.001
166 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.18 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.43409 (16)0.57524 (13)0.2348 (3)0.0691 (5)
O20.02639 (15)0.40900 (13)0.2335 (3)0.0688 (5)
N10.19755 (18)0.53428 (14)0.3789 (4)0.0565 (4)
H110.134 (3)0.5526 (18)0.491 (5)0.063 (6)*
N20.25155 (19)0.41618 (14)0.0232 (3)0.0589 (5)
H210.331 (3)0.4469 (19)0.017 (5)0.070 (7)*
C10.3307 (2)0.59059 (15)0.3924 (4)0.0537 (5)
C20.1534 (2)0.44946 (16)0.2065 (4)0.0543 (5)
C110.3432 (3)0.67318 (18)0.6154 (5)0.0641 (5)
H1120.252 (3)0.676 (2)0.715 (5)0.081 (7)*
H1110.427 (3)0.650 (2)0.729 (6)0.097 (9)*
C120.3788 (3)0.7864 (2)0.5310 (6)0.0760 (7)
H1210.400 (3)0.842 (2)0.704 (6)0.101 (9)*
H1220.480 (4)0.782 (2)0.415 (6)0.103 (9)*
C130.2550 (4)0.8377 (2)0.3726 (7)0.0996 (10)
H1310.234 (4)0.790 (3)0.224 (8)0.131 (12)*
C140.3084 (7)0.9468 (3)0.2766 (9)0.1566 (19)
H1430.22850.97900.17700.188*
H1420.39680.93590.16830.188*
H1410.33330.99390.42450.188*
C150.1083 (4)0.8540 (3)0.5295 (11)0.1496 (18)
H1530.03240.88690.42280.179*
H1510.12790.90000.68170.179*
H1520.07250.78520.58270.179*
C210.2176 (3)0.32596 (19)0.1566 (5)0.0652 (6)
H2120.111 (3)0.3305 (18)0.210 (5)0.069 (6)*
H2110.279 (3)0.3354 (19)0.316 (5)0.078 (7)*
C220.2497 (5)0.2186 (2)0.0422 (8)0.0929 (9)
H2230.229 (4)0.161 (3)0.165 (7)0.110 (10)*
H2220.188 (4)0.209 (2)0.100 (7)0.104 (10)*
H2210.363 (4)0.214 (3)0.001 (6)0.114 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0488 (7)0.0798 (10)0.0782 (10)0.0104 (6)0.0217 (7)0.0042 (8)
O20.0478 (8)0.0781 (10)0.0802 (10)0.0124 (7)0.0188 (7)0.0034 (8)
N10.0449 (8)0.0618 (10)0.0630 (10)0.0027 (7)0.0163 (7)0.0010 (8)
N20.0429 (8)0.0654 (10)0.0683 (11)0.0045 (7)0.0120 (7)0.0013 (8)
C10.0434 (9)0.0560 (10)0.0625 (11)0.0012 (7)0.0067 (8)0.0122 (9)
C20.0422 (9)0.0583 (11)0.0631 (11)0.0002 (7)0.0106 (8)0.0099 (9)
C110.0565 (12)0.0684 (13)0.0673 (13)0.0027 (10)0.0054 (10)0.0014 (10)
C120.0675 (14)0.0705 (14)0.0896 (17)0.0082 (11)0.0109 (12)0.0023 (13)
C130.133 (3)0.0673 (16)0.098 (2)0.0028 (16)0.0226 (19)0.0039 (15)
C140.258 (6)0.080 (2)0.135 (3)0.004 (3)0.005 (4)0.030 (2)
C150.089 (2)0.113 (3)0.247 (6)0.024 (2)0.025 (3)0.011 (3)
C210.0526 (11)0.0728 (14)0.0698 (14)0.0016 (9)0.0059 (10)0.0026 (11)
C220.102 (2)0.0703 (17)0.106 (2)0.0013 (15)0.0101 (19)0.0013 (16)
Geometric parameters (Å, º) top
O1—C11.224 (2)C13—C151.527 (5)
O2—C21.236 (2)C13—C141.534 (5)
N1—C11.366 (2)C13—H1310.96 (4)
N1—C21.398 (3)C14—H1430.9600
N1—H110.82 (3)C14—H1420.9600
N2—C21.325 (2)C14—H1410.9600
N2—C211.448 (3)C15—H1530.9600
N2—H210.80 (2)C15—H1510.9600
C1—C111.502 (3)C15—H1520.9600
C11—C121.519 (3)C21—C221.500 (4)
C11—H1120.95 (3)C21—H2120.98 (2)
C11—H1110.98 (3)C21—H2110.99 (3)
C12—C131.507 (4)C22—H2230.95 (3)
C12—H1211.12 (3)C22—H2220.92 (3)
C12—H1221.07 (3)C22—H2211.02 (4)
C1—N1—C2129.89 (17)C12—C13—H131108 (2)
C1—N1—H11115.1 (16)C15—C13—H131108 (2)
C2—N1—H11115.0 (16)C14—C13—H131109 (2)
C2—N2—C21121.34 (18)C13—C14—H143109.5
C2—N2—H21117.7 (18)C13—C14—H142109.5
C21—N2—H21120.9 (18)H143—C14—H142109.5
O1—C1—N1122.75 (19)C13—C14—H141109.5
O1—C1—C11121.63 (18)H143—C14—H141109.5
N1—C1—C11115.62 (17)H142—C14—H141109.5
O2—C2—N2123.54 (19)C13—C15—H153109.5
O2—C2—N1118.75 (17)C13—C15—H151109.5
N2—C2—N1117.71 (17)H153—C15—H151109.5
C1—C11—C12114.0 (2)C13—C15—H152109.5
C1—C11—H112110.6 (15)H153—C15—H152109.5
C12—C11—H112108.5 (16)H151—C15—H152109.5
C1—C11—H111107.6 (17)N2—C21—C22112.8 (2)
C12—C11—H111107.6 (16)N2—C21—H212109.0 (13)
H112—C11—H111108 (2)C22—C21—H212110.1 (13)
C13—C12—C11114.6 (2)N2—C21—H211107.1 (14)
C13—C12—H121106.5 (15)C22—C21—H211111.2 (14)
C11—C12—H121111.0 (15)H212—C21—H211106 (2)
C13—C12—H122108.0 (16)C21—C22—H223111 (2)
C11—C12—H122108.2 (16)C21—C22—H222110 (2)
H121—C12—H122108 (2)H223—C22—H222107 (3)
C12—C13—C15111.8 (3)C21—C22—H221108.9 (18)
C12—C13—C14110.2 (3)H223—C22—H221106 (3)
C15—C13—C14109.5 (3)H222—C22—H221113 (3)
C2—N1—C1—O13.4 (3)O1—C1—C11—C1255.6 (3)
C2—N1—C1—C11176.41 (19)N1—C1—C11—C12124.7 (2)
C21—N2—C2—O22.0 (3)C1—C11—C12—C1365.7 (3)
C21—N2—C2—N1177.44 (18)C11—C12—C13—C1563.1 (4)
C1—N1—C2—O2178.90 (19)C11—C12—C13—C14174.8 (3)
C1—N1—C2—N20.5 (3)C2—N2—C21—C2282.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.80 (2)2.44 (3)3.067 (2)136 (2)
N1—H11···O2ii0.82 (3)2.04 (3)2.858 (2)177 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl348K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.113 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.740 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.357 (2) ÅCell parameters from 2704 reflections
c = 5.1473 (12) Åθ = 1.7–26.9°
α = 91.509 (8)°µ = 0.08 mm1
β = 90.236 (11)°T = 348 K
γ = 89.525 (13)°Plate, colourless
V = 555.7 (2) Å30.80 × 0.40 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1418 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1010
Oscillation method scansk = 1515
6205 measured reflectionsl = 66
1939 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.082Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.255H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1229P)2 + 0.2315P]
where P = (Fo2 + 2Fc2)/3
1939 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.27 e Å3
5 restraintsΔρmin = 0.21 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.4329 (2)0.5747 (2)0.2314 (5)0.0846 (7)
O20.0266 (2)0.4099 (2)0.2382 (5)0.0837 (7)
N10.1972 (3)0.5337 (2)0.3770 (5)0.0701 (7)
H110.13020.55300.49130.084*
N20.2522 (3)0.4162 (2)0.0286 (5)0.0732 (7)
H210.33880.44830.01700.088*
C10.3299 (3)0.5903 (2)0.3881 (6)0.0684 (8)
C20.1534 (3)0.4499 (3)0.2098 (6)0.0689 (8)
C110.3418 (4)0.6722 (3)0.6063 (7)0.0805 (9)
H1120.42100.64880.72540.097*
H1110.24590.67400.70050.097*
C120.3776 (5)0.7849 (3)0.5237 (9)0.1003 (12)
H1220.47110.78270.42290.120*
H1210.39610.82990.67770.120*
C130.2532 (6)0.8367 (4)0.3649 (10)0.1236 (17)
H1310.23020.78970.21370.148*
C140.3071 (11)0.9462 (5)0.2717 (15)0.196 (4)
H1430.22800.97870.16920.235*
H1420.39750.93610.16820.235*
H1410.32980.99260.41920.235*
C150.1075 (6)0.8540 (5)0.5253 (17)0.185 (3)
H1520.07290.78560.58610.222*
H1530.02940.88570.41910.222*
H1510.12870.90150.67140.222*
C210.2180 (4)0.3277 (3)0.1486 (7)0.0808 (9)
H2110.27860.33450.30460.097*
H2120.11090.33170.19810.097*
C220.2497 (6)0.2198 (3)0.0343 (10)0.1109 (14)
H2230.22470.16350.15910.133*
H2220.18870.21200.11870.133*
H2210.35610.21450.01100.133*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0539 (12)0.0981 (16)0.1021 (16)0.0133 (10)0.0244 (11)0.0008 (13)
O20.0553 (13)0.0932 (15)0.1029 (17)0.0144 (10)0.0238 (11)0.0022 (13)
N10.0513 (13)0.0771 (15)0.0822 (16)0.0061 (11)0.0199 (11)0.0039 (13)
N20.0508 (13)0.0810 (16)0.0878 (17)0.0061 (11)0.0168 (12)0.0008 (14)
C10.0514 (15)0.0752 (17)0.0796 (19)0.0018 (12)0.0091 (13)0.0186 (15)
C20.0480 (15)0.0787 (18)0.0809 (19)0.0023 (12)0.0141 (13)0.0139 (15)
C110.0653 (19)0.084 (2)0.092 (2)0.0069 (15)0.0076 (16)0.0038 (18)
C120.085 (3)0.095 (3)0.121 (3)0.013 (2)0.016 (2)0.004 (2)
C130.157 (5)0.094 (3)0.120 (4)0.001 (3)0.020 (3)0.011 (3)
C140.299 (11)0.105 (4)0.186 (7)0.006 (5)0.006 (7)0.048 (4)
C150.102 (4)0.143 (5)0.312 (10)0.027 (3)0.020 (5)0.028 (6)
C210.0619 (19)0.092 (2)0.089 (2)0.0042 (15)0.0082 (16)0.0021 (18)
C220.115 (3)0.086 (3)0.131 (4)0.001 (2)0.007 (3)0.004 (2)
Geometric parameters (Å, º) top
O1—C11.222 (4)C13—C141.526 (8)
O2—C21.228 (3)C13—C151.531 (9)
N1—C11.359 (4)C13—H1310.9800
N1—C21.385 (4)C14—H1430.9600
N1—H110.8600C14—H1420.9600
N2—C21.330 (4)C14—H1410.9600
N2—C211.439 (4)C15—H1520.9600
N2—H210.8600C15—H1530.9600
C1—C111.496 (5)C15—H1510.9600
C11—C121.503 (5)C21—C221.495 (5)
C11—H1120.9700C21—H2110.9700
C11—H1110.9700C21—H2120.9700
C12—C131.506 (7)C22—H2230.9600
C12—H1220.9700C22—H2220.9600
C12—H1210.9700C22—H2210.9600
C1—N1—C2129.9 (3)C12—C13—H131109.1
C1—N1—H11115.1C14—C13—H131109.1
C2—N1—H11115.1C15—C13—H131109.1
C2—N2—C21121.7 (3)C13—C14—H143109.5
C2—N2—H21119.2C13—C14—H142109.5
C21—N2—H21119.2H143—C14—H142109.5
O1—C1—N1122.3 (3)C13—C14—H141109.5
O1—C1—C11122.2 (3)H143—C14—H141109.5
N1—C1—C11115.5 (3)H142—C14—H141109.5
O2—C2—N2123.6 (3)C13—C15—H152109.5
O2—C2—N1118.4 (3)C13—C15—H153109.5
N2—C2—N1118.0 (3)H152—C15—H153109.5
C1—C11—C12114.6 (3)C13—C15—H151109.5
C1—C11—H112108.6H152—C15—H151109.5
C12—C11—H112108.6H153—C15—H151109.5
C1—C11—H111108.6N2—C21—C22112.6 (3)
C12—C11—H111108.6N2—C21—H211109.1
H112—C11—H111107.6C22—C21—H211109.1
C11—C12—C13114.1 (3)N2—C21—H212109.1
C11—C12—H122108.7C22—C21—H212109.1
C13—C12—H122108.7H211—C21—H212107.8
C11—C12—H121108.7C21—C22—H223109.5
C13—C12—H121108.7C21—C22—H222109.5
H122—C12—H121107.6H223—C22—H222109.5
C12—C13—C14109.6 (5)C21—C22—H221109.5
C12—C13—C15111.0 (4)H223—C22—H221109.5
C14—C13—C15108.8 (5)H222—C22—H221109.5
C2—N1—C1—O13.0 (5)O1—C1—C11—C1255.3 (4)
C2—N1—C1—C11176.5 (3)N1—C1—C11—C12125.3 (3)
C21—N2—C2—O21.0 (5)C1—C11—C12—C1365.7 (5)
C21—N2—C2—N1178.3 (3)C11—C12—C13—C14175.0 (4)
C1—N1—C2—O2179.3 (3)C11—C12—C13—C1564.8 (6)
C1—N1—C2—N20.1 (5)C2—N2—C21—C2282.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.393.069 (3)137
N1—H11···O2ii0.862.002.859 (3)177
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl350K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.107 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.7514 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.460 (2) ÅCell parameters from 4431 reflections
c = 5.1254 (9) Åθ = 2.9–27.4°
α = 91.510 (5)°µ = 0.08 mm1
β = 90.273 (9)°T = 350 K
γ = 89.642 (8)°Plate, colourless
V = 558.69 (16) Å30.80 × 0.40 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1790 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
6495 measured reflectionsl = 66
2118 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.120Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.250H-atom parameters constrained
S = 1.34 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.4679P]
where P = (Fo2 + 2Fc2)/3
2118 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.20 e Å3
6 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.4331 (3)0.5744 (2)0.2313 (6)0.0800 (9)
O20.0270 (3)0.4095 (2)0.2386 (6)0.0797 (9)
N10.1970 (3)0.5338 (3)0.3786 (7)0.0657 (9)
H110.13040.55290.49390.079*
N20.2526 (4)0.4162 (3)0.0302 (7)0.0683 (9)
H120.33920.44780.01900.082*
C10.3300 (4)0.5901 (3)0.3871 (8)0.0623 (10)
C20.1535 (4)0.4499 (3)0.2105 (8)0.0633 (10)
C110.3413 (5)0.6722 (3)0.6048 (9)0.0775 (12)
H1120.42030.64960.72520.093*
H1110.24530.67390.69880.093*
C120.3767 (6)0.7844 (4)0.5202 (11)0.1012 (17)
H1220.39680.82890.67460.121*
H1210.46940.78200.41720.121*
C130.2530 (8)0.8371 (5)0.3637 (13)0.123 (2)
H1310.22920.79130.21070.148*
C140.3071 (13)0.9459 (5)0.2724 (18)0.201 (5)
H1430.22770.97880.17180.242*
H1420.39660.93620.16660.242*
H1410.33100.99110.42140.242*
C150.1083 (8)0.8548 (7)0.523 (2)0.192 (4)
H1520.07410.78730.58720.230*
H1530.03010.88520.41540.230*
H1510.12940.90300.66810.230*
C210.2183 (5)0.3279 (4)0.1466 (9)0.0788 (12)
H2110.27850.33480.30370.095*
H2120.11130.33170.19590.095*
C220.2505 (7)0.2204 (4)0.0324 (12)0.1091 (18)
H2230.22620.16470.15860.131*
H2220.18910.21210.12050.131*
H2210.35670.21550.01410.131*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0511 (15)0.095 (2)0.094 (2)0.0123 (14)0.0241 (15)0.0030 (17)
O20.0525 (16)0.092 (2)0.095 (2)0.0142 (14)0.0228 (14)0.0050 (17)
N10.0484 (17)0.073 (2)0.076 (2)0.0032 (14)0.0209 (15)0.0020 (17)
N20.0504 (17)0.074 (2)0.080 (2)0.0057 (15)0.0134 (16)0.0016 (18)
C10.049 (2)0.067 (2)0.072 (2)0.0016 (17)0.0082 (18)0.0141 (19)
C20.0451 (19)0.071 (2)0.075 (3)0.0033 (17)0.0150 (18)0.010 (2)
C110.064 (3)0.082 (3)0.087 (3)0.006 (2)0.010 (2)0.004 (2)
C120.087 (4)0.097 (4)0.120 (4)0.012 (3)0.026 (3)0.005 (3)
C130.145 (6)0.105 (4)0.120 (5)0.005 (4)0.020 (4)0.015 (4)
C140.316 (14)0.098 (5)0.192 (9)0.006 (7)0.019 (9)0.047 (6)
C150.109 (6)0.147 (7)0.321 (14)0.029 (5)0.021 (7)0.029 (8)
C210.060 (2)0.092 (3)0.084 (3)0.003 (2)0.010 (2)0.001 (3)
C220.114 (4)0.086 (4)0.127 (5)0.002 (3)0.010 (4)0.001 (3)
Geometric parameters (Å, º) top
O1—C11.219 (4)C13—C151.523 (11)
O2—C21.230 (4)C13—C141.524 (10)
N1—C11.362 (5)C13—H1310.9800
N1—C21.391 (5)C14—H1430.9600
N1—H110.8600C14—H1420.9600
N2—C21.329 (5)C14—H1410.9600
N2—C211.438 (5)C15—H1520.9600
N2—H120.8600C15—H1530.9600
C1—C111.496 (6)C15—H1510.9600
C11—C121.510 (7)C21—C221.501 (7)
C11—H1120.9700C21—H2110.9700
C11—H1110.9700C21—H2120.9700
C12—C131.502 (9)C22—H2230.9600
C12—H1220.9700C22—H2220.9600
C12—H1210.9700C22—H2210.9600
C1—N1—C2129.3 (3)C12—C13—H131109.0
C1—N1—H11115.3C15—C13—H131109.0
C2—N1—H11115.3C14—C13—H131109.0
C2—N2—C21121.6 (3)C13—C14—H143109.5
C2—N2—H12119.2C13—C14—H142109.5
C21—N2—H12119.2H143—C14—H142109.5
O1—C1—N1122.8 (4)C13—C14—H141109.5
O1—C1—C11122.3 (4)H143—C14—H141109.5
N1—C1—C11115.0 (3)H142—C14—H141109.5
O2—C2—N2123.3 (4)C13—C15—H152109.5
O2—C2—N1118.7 (3)C13—C15—H153109.5
N2—C2—N1118.0 (3)H152—C15—H153109.5
C1—C11—C12114.8 (4)C13—C15—H151109.5
C1—C11—H112108.6H152—C15—H151109.5
C12—C11—H112108.6H153—C15—H151109.5
C1—C11—H111108.6N2—C21—C22113.1 (4)
C12—C11—H111108.6N2—C21—H211109.0
H112—C11—H111107.5C22—C21—H211109.0
C13—C12—C11115.0 (4)N2—C21—H212109.0
C13—C12—H122108.5C22—C21—H212109.0
C11—C12—H122108.5H211—C21—H212107.8
C13—C12—H121108.5C21—C22—H223109.5
C11—C12—H121108.5C21—C22—H222109.5
H122—C12—H121107.5H223—C22—H222109.5
C12—C13—C15111.6 (6)C21—C22—H221109.5
C12—C13—C14110.0 (6)H223—C22—H221109.5
C15—C13—C14108.2 (7)H222—C22—H221109.5
C2—N1—C1—O12.3 (7)O1—C1—C11—C1255.4 (6)
C2—N1—C1—C11176.9 (4)N1—C1—C11—C12125.3 (4)
C21—N2—C2—O20.4 (6)C1—C11—C12—C1366.8 (6)
C21—N2—C2—N1178.3 (4)C11—C12—C13—C1564.3 (7)
C1—N1—C2—O2179.4 (4)C11—C12—C13—C14175.6 (5)
C1—N1—C2—N20.7 (6)C2—N2—C21—C2283.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H12···O1i0.862.393.070 (4)137
N1—H11···O2ii0.861.992.853 (4)178
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl352K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.116 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.7503 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.4205 (13) ÅCell parameters from 2561 reflections
c = 5.0998 (3) Åθ = 1.6–27.2°
α = 90.921 (8)°µ = 0.08 mm1
β = 89.723 (12)°T = 352 K
γ = 89.714 (10)°Plate, colourless
V = 554.18 (12) Å30.80 × 0.40 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1242 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
Graphite monochromatorθmax = 27.5°, θmin = 2.8°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
6495 measured reflectionsl = 66
1968 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.109Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.357H-atom parameters constrained
S = 2.28 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
1968 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.25 e Å3
5 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.4334 (3)0.5747 (3)0.2302 (6)0.0916 (10)
O20.0271 (3)0.4095 (2)0.2407 (6)0.0884 (10)
N10.1975 (4)0.5334 (3)0.3774 (6)0.0736 (10)
H110.13060.55140.49430.088*
N20.2528 (4)0.4164 (3)0.0297 (6)0.0762 (10)
H210.33970.44800.01710.091*
C10.3279 (4)0.5905 (3)0.3858 (8)0.0713 (10)
C20.1544 (5)0.4503 (3)0.2098 (8)0.0745 (10)
C110.3418 (5)0.6719 (3)0.6031 (9)0.0841 (12)
H1120.42000.64750.72280.101*
H1110.24600.67460.69920.101*
C120.3806 (6)0.7842 (4)0.5206 (11)0.1075 (17)
H1220.47330.78200.41560.129*
H1210.40040.82810.67560.129*
C130.2535 (8)0.8365 (5)0.3631 (12)0.131 (2)
H1310.23080.79030.21090.157*
C140.3088 (15)0.9449 (6)0.2663 (19)0.220 (6)
H1420.40070.93480.16510.264*
H1410.32910.99160.41390.264*
H1430.23150.97680.15890.264*
C150.1084 (8)0.8520 (7)0.524 (2)0.188 (4)
H1520.07390.78350.58490.225*
H1530.03080.88390.41780.225*
H1510.12890.89840.67220.225*
C210.2191 (5)0.3275 (4)0.1474 (9)0.0883 (13)
H2110.27980.33470.30570.106*
H2120.11220.33130.19640.106*
C220.2506 (8)0.2200 (4)0.0318 (13)0.1205 (19)
H2230.22630.16440.15750.145*
H2220.18900.21150.12270.145*
H2210.35670.21500.01360.145*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0625 (17)0.104 (2)0.108 (2)0.0180 (14)0.0261 (15)0.0071 (17)
O20.0576 (17)0.101 (2)0.106 (2)0.0170 (13)0.0298 (14)0.0096 (16)
N10.0580 (18)0.081 (2)0.0813 (19)0.0088 (14)0.0220 (14)0.0016 (16)
N20.0542 (18)0.085 (2)0.089 (2)0.0068 (14)0.0168 (15)0.0017 (17)
C10.0460 (18)0.081 (2)0.087 (2)0.0021 (15)0.0141 (15)0.017 (2)
C20.055 (2)0.082 (2)0.086 (2)0.0021 (16)0.0158 (17)0.010 (2)
C110.071 (3)0.082 (2)0.098 (3)0.0082 (19)0.010 (2)0.004 (2)
C120.084 (3)0.103 (4)0.135 (4)0.012 (3)0.024 (3)0.009 (3)
C130.162 (7)0.108 (4)0.123 (5)0.003 (4)0.011 (4)0.011 (3)
C140.34 (2)0.125 (6)0.193 (9)0.002 (7)0.005 (10)0.047 (6)
C150.105 (6)0.165 (7)0.294 (12)0.022 (5)0.012 (7)0.029 (7)
C210.067 (3)0.096 (3)0.101 (3)0.008 (2)0.018 (2)0.005 (2)
C220.133 (5)0.098 (4)0.130 (5)0.008 (3)0.007 (4)0.003 (3)
Geometric parameters (Å, º) top
O1—C11.228 (4)C13—C151.519 (11)
O2—C21.237 (5)C13—C141.522 (10)
N1—C11.346 (5)C13—H1310.9800
N1—C21.384 (5)C14—H1420.9600
N1—H110.8600C14—H1410.9600
N2—C21.319 (5)C14—H1430.9600
N2—C211.448 (5)C15—H1520.9600
N2—H210.8600C15—H1530.9600
C1—C111.494 (6)C15—H1510.9600
C11—C121.503 (6)C21—C221.493 (7)
C11—H1120.9700C21—H2110.9700
C11—H1110.9700C21—H2120.9700
C12—C131.524 (8)C22—H2230.9600
C12—H1220.9700C22—H2220.9600
C12—H1210.9700C22—H2210.9600
C1—N1—C2130.1 (3)C15—C13—H131108.7
C1—N1—H11114.9C14—C13—H131108.7
C2—N1—H11114.9C12—C13—H131108.7
C2—N2—C21122.0 (4)C13—C14—H142109.5
C2—N2—H21119.0C13—C14—H141109.5
C21—N2—H21119.0H142—C14—H141109.5
O1—C1—N1122.4 (4)C13—C14—H143109.5
O1—C1—C11120.8 (4)H142—C14—H143109.5
N1—C1—C11116.7 (3)H141—C14—H143109.5
O2—C2—N2123.1 (4)C13—C15—H152109.5
O2—C2—N1118.5 (3)C13—C15—H153109.5
N2—C2—N1118.4 (4)H152—C15—H153109.5
C1—C11—C12115.6 (4)C13—C15—H151109.5
C1—C11—H112108.4H152—C15—H151109.5
C12—C11—H112108.4H153—C15—H151109.5
C1—C11—H111108.4N2—C21—C22113.2 (4)
C12—C11—H111108.4N2—C21—H211108.9
H112—C11—H111107.4C22—C21—H211108.9
C11—C12—C13112.7 (4)N2—C21—H212108.9
C11—C12—H122109.1C22—C21—H212108.9
C13—C12—H122109.1H211—C21—H212107.8
C11—C12—H121109.1C21—C22—H223109.5
C13—C12—H121109.1C21—C22—H222109.5
H122—C12—H121107.8H223—C22—H222109.5
C15—C13—C14109.7 (8)C21—C22—H221109.5
C15—C13—C12112.0 (5)H223—C22—H221109.5
C14—C13—C12108.9 (6)H222—C22—H221109.5
C2—N1—C1—O10.6 (6)O1—C1—C11—C1255.9 (5)
C2—N1—C1—C11176.8 (3)N1—C1—C11—C12126.7 (4)
C21—N2—C2—O20.2 (6)C1—C11—C12—C1366.3 (6)
C21—N2—C2—N1177.8 (3)C11—C12—C13—C1563.9 (8)
C1—N1—C2—O2179.9 (4)C11—C12—C13—C14174.6 (6)
C1—N1—C2—N21.8 (6)C2—N2—C21—C2283.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.363.047 (4)137
N1—H11···O2ii0.861.982.840 (4)179
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl354K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.094 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.7270 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.6010 (13) ÅCell parameters from 4364 reflections
c = 5.1459 (3) Åθ = 2.9–27.5°
α = 91.317 (9)°µ = 0.08 mm1
β = 90.331 (11)°T = 354 K
γ = 89.001 (9)°Plate, colourless
V = 565.65 (7) Å30.80 × 0.40 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1551 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
6513 measured reflectionsl = 66
2122 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.118Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.277H-atom parameters constrained
S = 1.31 w = 1/[σ2(Fo2) + (0.0663P)2 + 0.4317P]
where P = (Fo2 + 2Fc2)/3
2122 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.22 e Å3
5 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.4326 (3)0.5747 (3)0.2307 (7)0.0861 (10)
O20.0267 (3)0.4098 (3)0.2401 (7)0.0852 (10)
N10.1973 (4)0.5339 (3)0.3778 (7)0.0709 (10)
H110.13030.55310.49230.085*
N20.2522 (4)0.4164 (3)0.0306 (7)0.0712 (10)
H210.33830.44800.01690.085*
C10.3297 (4)0.5903 (3)0.3861 (9)0.0666 (11)
C20.1532 (4)0.4496 (3)0.2123 (9)0.0661 (11)
C110.3404 (5)0.6721 (4)0.6014 (10)0.0811 (13)
H1120.41890.64920.72290.097*
H1110.24370.67470.69370.097*
C120.3767 (7)0.7834 (4)0.5180 (13)0.112 (2)
H1210.39640.82680.67230.134*
H1220.47020.78030.41680.134*
C130.2538 (8)0.8369 (5)0.3608 (14)0.131 (2)
H1310.23070.79220.20780.157*
C140.3074 (14)0.9447 (6)0.271 (2)0.219 (5)
H1430.22790.97770.16980.262*
H1420.39760.93500.16630.262*
H1410.33050.98900.41950.262*
C150.1081 (9)0.8545 (7)0.518 (2)0.209 (5)
H1520.07480.78790.58210.250*
H1530.02960.88430.40880.250*
H1510.12800.90240.66130.250*
C210.2180 (5)0.3283 (4)0.1443 (10)0.0819 (13)
H2110.27830.33450.30090.098*
H2120.11070.33280.19380.098*
C220.2503 (8)0.2210 (4)0.0295 (13)0.116 (2)
H2230.22510.16630.15470.140*
H2220.18930.21340.12340.140*
H2210.35690.21500.01570.140*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0583 (17)0.102 (2)0.098 (2)0.0109 (15)0.0267 (16)0.0047 (19)
O20.0544 (16)0.100 (2)0.102 (2)0.0142 (15)0.0237 (15)0.0063 (18)
N10.0523 (18)0.079 (2)0.082 (2)0.0025 (16)0.0237 (17)0.001 (2)
N20.0510 (18)0.082 (2)0.081 (2)0.0032 (16)0.0158 (16)0.0026 (19)
C10.053 (2)0.071 (3)0.077 (3)0.0035 (18)0.0116 (19)0.016 (2)
C20.049 (2)0.074 (3)0.076 (3)0.0056 (18)0.0106 (19)0.014 (2)
C110.068 (3)0.083 (3)0.092 (3)0.003 (2)0.014 (2)0.005 (3)
C120.098 (4)0.106 (4)0.132 (5)0.011 (3)0.028 (4)0.010 (4)
C130.151 (7)0.113 (5)0.129 (6)0.014 (5)0.017 (5)0.025 (4)
C140.342 (16)0.108 (6)0.208 (10)0.001 (8)0.033 (10)0.045 (6)
C150.120 (7)0.166 (8)0.340 (16)0.035 (6)0.023 (9)0.032 (9)
C210.062 (2)0.098 (3)0.086 (3)0.002 (2)0.012 (2)0.000 (3)
C220.121 (5)0.092 (4)0.136 (5)0.003 (3)0.012 (4)0.001 (4)
Geometric parameters (Å, º) top
O1—C11.217 (5)C13—C151.520 (11)
O2—C21.232 (5)C13—C141.527 (11)
N1—C11.367 (5)C13—H1310.9800
N1—C21.403 (6)C14—H1430.9600
N1—H110.8600C14—H1420.9600
N2—C21.332 (5)C14—H1410.9600
N2—C211.447 (6)C15—H1520.9600
N2—H210.8600C15—H1530.9600
C1—C111.499 (6)C15—H1510.9600
C11—C121.516 (7)C21—C221.510 (8)
C11—H1120.9700C21—H2110.9700
C11—H1110.9700C21—H2120.9700
C12—C131.500 (9)C22—H2230.9600
C12—H1210.9700C22—H2220.9600
C12—H1220.9700C22—H2210.9600
C1—N1—C2130.3 (3)C12—C13—H131108.9
C1—N1—H11114.9C15—C13—H131108.9
C2—N1—H11114.9C14—C13—H131108.9
C2—N2—C21121.4 (4)C13—C14—H143109.5
C2—N2—H21119.3C13—C14—H142109.5
C21—N2—H21119.3H143—C14—H142109.5
O1—C1—N1122.4 (4)C13—C14—H141109.5
O1—C1—C11122.1 (4)H143—C14—H141109.5
N1—C1—C11115.5 (4)H142—C14—H141109.5
O2—C2—N2123.0 (4)C13—C15—H152109.5
O2—C2—N1119.4 (4)C13—C15—H153109.5
N2—C2—N1117.6 (3)H152—C15—H153109.5
C1—C11—C12115.6 (4)C13—C15—H151109.5
C1—C11—H112108.4H152—C15—H151109.5
C12—C11—H112108.4H153—C15—H151109.5
C1—C11—H111108.4N2—C21—C22113.7 (4)
C12—C11—H111108.4N2—C21—H211108.8
H112—C11—H111107.4C22—C21—H211108.8
C13—C12—C11115.0 (5)N2—C21—H212108.8
C13—C12—H121108.5C22—C21—H212108.8
C11—C12—H121108.5H211—C21—H212107.7
C13—C12—H122108.5C21—C22—H223109.5
C11—C12—H122108.5C21—C22—H222109.5
H121—C12—H122107.5H223—C22—H222109.5
C12—C13—C15111.4 (6)C21—C22—H221109.5
C12—C13—C14110.5 (7)H223—C22—H221109.5
C15—C13—C14108.2 (8)H222—C22—H221109.5
C2—N1—C1—O12.7 (7)O1—C1—C11—C1254.2 (6)
C2—N1—C1—C11176.8 (4)N1—C1—C11—C12126.4 (4)
C21—N2—C2—O21.5 (7)C1—C11—C12—C1366.9 (6)
C21—N2—C2—N1178.4 (4)C11—C12—C13—C1564.0 (8)
C1—N1—C2—O2179.8 (4)C11—C12—C13—C14175.8 (6)
C1—N1—C2—N20.1 (6)C2—N2—C21—C2282.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.393.073 (4)137
N1—H11···O2ii0.861.992.850 (5)177
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl356K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.108 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.726 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.460 (3) ÅCell parameters from 2070 reflections
c = 5.1382 (12) Åθ = 2.3–27.5°
α = 91.423 (6)°µ = 0.08 mm1
β = 90.143 (10)°T = 356 K
γ = 89.297 (11)°Plate, colourless
V = 558.5 (2) Å30.80 × 0.80 × 0.20 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1306 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1011
Oscillation method scansk = 1515
6409 measured reflectionsl = 66
1713 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.250H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1254P)2 + 0.2162P]
where P = (Fo2 + 2Fc2)/3
1713 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.23 e Å3
5 restraintsΔρmin = 0.24 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.4321 (3)0.5743 (2)0.2297 (5)0.0906 (8)
O20.0271 (3)0.4103 (2)0.2409 (5)0.0873 (8)
N10.1970 (3)0.5337 (2)0.3769 (5)0.0726 (8)
H110.13020.55270.49230.087*
N20.2523 (3)0.4164 (2)0.0323 (5)0.0759 (8)
H210.33900.44790.02070.091*
C10.3290 (4)0.5900 (3)0.3840 (6)0.0721 (9)
C20.1537 (4)0.4496 (3)0.2106 (6)0.0708 (8)
C110.3411 (4)0.6720 (3)0.5999 (7)0.0851 (10)
H1120.42000.64870.72000.102*
H1110.24480.67460.69400.102*
C120.3775 (5)0.7834 (3)0.5164 (10)0.1125 (14)
H1220.47080.78030.41400.135*
H1210.39750.82760.67050.135*
C130.2533 (7)0.8369 (4)0.3592 (11)0.138 (2)
H1310.23040.79110.20660.165*
C140.3084 (12)0.9448 (5)0.2669 (17)0.217 (4)
H1430.22990.97770.16360.260*
H1420.39930.93430.16390.260*
H1410.33090.99050.41490.260*
C150.1063 (8)0.8539 (6)0.5178 (19)0.205 (4)
H1520.07220.78610.57930.246*
H1530.02830.88490.41000.246*
H1510.12620.90140.66370.246*
C210.2181 (4)0.3286 (3)0.1433 (7)0.0846 (10)
H2110.27870.33500.30000.102*
H2120.11090.33280.19260.102*
C220.2501 (7)0.2215 (3)0.0277 (10)0.1194 (15)
H2230.22600.16560.15280.143*
H2220.18820.21370.12480.143*
H2210.35640.21630.01890.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0631 (14)0.1048 (18)0.1040 (17)0.0101 (12)0.0276 (13)0.0024 (14)
O20.0605 (15)0.0961 (16)0.1052 (18)0.0090 (11)0.0257 (12)0.0039 (13)
N10.0594 (15)0.0782 (17)0.0803 (16)0.0007 (12)0.0216 (12)0.0030 (13)
N20.0572 (15)0.0836 (18)0.0868 (18)0.0003 (12)0.0171 (12)0.0004 (14)
C10.0579 (18)0.0747 (19)0.085 (2)0.0035 (14)0.0125 (15)0.0196 (16)
C20.0550 (17)0.0787 (19)0.079 (2)0.0058 (14)0.0136 (14)0.0123 (16)
C110.078 (2)0.082 (2)0.095 (2)0.0011 (17)0.0099 (18)0.0000 (18)
C120.100 (3)0.103 (3)0.135 (4)0.010 (2)0.025 (3)0.006 (3)
C130.165 (6)0.107 (3)0.142 (4)0.012 (3)0.021 (4)0.016 (3)
C140.333 (14)0.110 (4)0.210 (8)0.003 (6)0.015 (8)0.047 (5)
C150.122 (6)0.162 (6)0.331 (12)0.038 (4)0.011 (7)0.022 (7)
C210.065 (2)0.097 (2)0.091 (2)0.0017 (17)0.0127 (16)0.0025 (19)
C220.134 (4)0.092 (3)0.132 (4)0.007 (3)0.007 (3)0.003 (3)
Geometric parameters (Å, º) top
O1—C11.211 (4)C13—C141.520 (9)
O2—C21.225 (4)C13—C151.532 (10)
N1—C11.357 (4)C13—H1310.9800
N1—C21.390 (4)C14—H1430.9600
N1—H110.8600C14—H1420.9600
N2—C21.314 (4)C14—H1410.9600
N2—C211.435 (4)C15—H1520.9600
N2—H210.8600C15—H1530.9600
C1—C111.494 (5)C15—H1510.9600
C11—C121.501 (6)C21—C221.497 (6)
C11—H1120.9700C21—H2110.9700
C11—H1110.9700C21—H2120.9700
C12—C131.509 (8)C22—H2230.9600
C12—H1220.9700C22—H2220.9600
C12—H1210.9700C22—H2210.9600
C1—N1—C2129.6 (3)C12—C13—H131108.7
C1—N1—H11115.2C14—C13—H131108.7
C2—N1—H11115.2C15—C13—H131108.7
C2—N2—C21121.3 (3)C13—C14—H143109.5
C2—N2—H21119.3C13—C14—H142109.5
C21—N2—H21119.3H143—C14—H142109.5
O1—C1—N1122.9 (3)C13—C14—H141109.5
O1—C1—C11121.7 (3)H143—C14—H141109.5
N1—C1—C11115.5 (3)H142—C14—H141109.5
O2—C2—N2124.1 (3)C13—C15—H152109.5
O2—C2—N1118.2 (3)C13—C15—H153109.5
N2—C2—N1117.7 (3)H152—C15—H153109.5
C1—C11—C12115.1 (3)C13—C15—H151109.5
C1—C11—H112108.5H152—C15—H151109.5
C12—C11—H112108.5H153—C15—H151109.5
C1—C11—H111108.5N2—C21—C22112.7 (3)
C12—C11—H111108.5N2—C21—H211109.0
H112—C11—H111107.5C22—C21—H211109.0
C11—C12—C13114.7 (4)N2—C21—H212109.0
C11—C12—H122108.6C22—C21—H212109.0
C13—C12—H122108.6H211—C21—H212107.8
C11—C12—H121108.6C21—C22—H223109.5
C13—C12—H121108.6C21—C22—H222109.5
H122—C12—H121107.6H223—C22—H222109.5
C12—C13—C14109.9 (6)C21—C22—H221109.5
C12—C13—C15111.6 (5)H223—C22—H221109.5
C14—C13—C15109.2 (6)H222—C22—H221109.5
C2—N1—C1—O12.0 (5)O1—C1—C11—C1255.1 (5)
C2—N1—C1—C11176.7 (3)N1—C1—C11—C12126.2 (3)
C21—N2—C2—O20.5 (5)C1—C11—C12—C1366.6 (5)
C21—N2—C2—N1178.6 (3)C11—C12—C13—C14175.2 (5)
C1—N1—C2—O2180.0 (3)C11—C12—C13—C1563.5 (6)
C1—N1—C2—N20.8 (5)C2—N2—C21—C2283.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.393.073 (4)137
N1—H11···O2ii0.861.982.844 (4)177
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl358K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.095 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.7438 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.5269 (10) ÅCell parameters from 2719 reflections
c = 5.1573 (4) Åθ = 4.0–27.4°
α = 90.802 (6)°µ = 0.08 mm1
β = 90.388 (7)°T = 358 K
γ = 89.224 (3)°Plate, colourless
V = 564.77 (7) Å31.00 × 1.00 × 0.20 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1516 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
Graphite monochromatorθmax = 27.4°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
6499 measured reflectionsl = 66
2397 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.103Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.298H-atom parameters constrained
S = 1.83 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
2397 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.36 e Å3
5 restraintsΔρmin = 0.28 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.4322 (2)0.57411 (19)0.2289 (5)0.0866 (7)
O20.0270 (2)0.40995 (18)0.2426 (5)0.0839 (7)
N10.1973 (2)0.53358 (18)0.3763 (5)0.0685 (7)
H110.13060.55240.49050.082*
N20.2522 (3)0.4163 (2)0.0331 (5)0.0731 (7)
H210.33890.44740.02150.088*
C10.3293 (3)0.5898 (2)0.3831 (6)0.0685 (8)
C20.1542 (3)0.4499 (2)0.2113 (6)0.0677 (7)
C110.3410 (4)0.6723 (2)0.6002 (7)0.0828 (9)
H1120.24460.67490.69230.099*
H1110.41940.64890.72150.099*
C120.3775 (5)0.7827 (3)0.5155 (9)0.1082 (13)
H1220.47060.77950.41420.130*
H1210.39760.82640.66830.130*
C130.2537 (6)0.8362 (4)0.3571 (10)0.1355 (18)
H1310.23160.79110.20500.163*
C140.3083 (11)0.9447 (5)0.2640 (17)0.222 (4)
H1430.22950.97760.16070.267*
H1420.39880.93490.16190.267*
H1410.33060.98970.41130.267*
C150.1067 (7)0.8530 (6)0.5095 (17)0.204 (4)
H1530.03070.88610.40090.244*
H1510.12630.89810.65770.244*
H1520.07040.78520.56620.244*
C210.2184 (4)0.3287 (3)0.1431 (7)0.0823 (9)
H2110.27970.33540.29800.099*
H2120.11170.33330.19460.099*
C220.2493 (5)0.2215 (3)0.0267 (10)0.1145 (14)
H2230.22480.16650.15100.137*
H2220.18760.21380.12490.137*
H2210.35550.21570.02050.137*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0643 (12)0.0974 (15)0.0986 (16)0.0124 (10)0.0275 (11)0.0013 (12)
O20.0601 (12)0.0913 (14)0.1009 (16)0.0127 (9)0.0233 (10)0.0026 (12)
N10.0559 (12)0.0734 (14)0.0766 (15)0.0013 (10)0.0194 (10)0.0026 (12)
N20.0567 (13)0.0770 (15)0.0859 (17)0.0015 (10)0.0183 (11)0.0011 (12)
C10.0560 (14)0.0729 (16)0.0771 (18)0.0034 (11)0.0139 (12)0.0141 (13)
C20.0534 (13)0.0737 (16)0.0764 (18)0.0043 (11)0.0155 (12)0.0136 (14)
C110.0733 (18)0.0785 (19)0.097 (2)0.0010 (14)0.0112 (16)0.0006 (17)
C120.104 (3)0.094 (3)0.127 (3)0.011 (2)0.027 (2)0.009 (2)
C130.163 (5)0.101 (3)0.142 (4)0.008 (3)0.022 (4)0.014 (3)
C140.351 (13)0.109 (4)0.208 (8)0.010 (5)0.035 (8)0.048 (5)
C150.132 (5)0.145 (5)0.332 (11)0.029 (4)0.038 (7)0.009 (6)
C210.0658 (17)0.091 (2)0.090 (2)0.0008 (14)0.0127 (15)0.0019 (17)
C220.120 (3)0.089 (3)0.134 (3)0.006 (2)0.009 (3)0.004 (2)
Geometric parameters (Å, º) top
O1—C11.217 (3)C13—C151.522 (9)
O2—C21.238 (3)C13—C141.531 (8)
N1—C11.361 (4)C13—H1310.9800
N1—C21.395 (4)C14—H1430.9600
N1—H110.8600C14—H1420.9600
N2—C21.322 (4)C14—H1410.9600
N2—C211.447 (4)C15—H1530.9600
N2—H210.8600C15—H1510.9600
C1—C111.516 (5)C15—H1520.9600
C11—C121.495 (5)C21—C221.498 (5)
C11—H1120.9700C21—H2110.9700
C11—H1110.9700C21—H2120.9700
C12—C131.508 (7)C22—H2230.9600
C12—H1220.9700C22—H2220.9600
C12—H1210.9700C22—H2210.9600
C1—N1—C2129.5 (2)C12—C13—H131108.6
C1—N1—H11115.2C15—C13—H131108.6
C2—N1—H11115.2C14—C13—H131108.6
C2—N2—C21122.1 (2)C13—C14—H143109.5
C2—N2—H21118.9C13—C14—H142109.5
C21—N2—H21118.9H143—C14—H142109.5
O1—C1—N1122.6 (3)C13—C14—H141109.5
O1—C1—C11122.1 (3)H143—C14—H141109.5
N1—C1—C11115.3 (2)H142—C14—H141109.5
O2—C2—N2123.5 (3)C13—C15—H153109.5
O2—C2—N1118.2 (3)C13—C15—H151109.5
N2—C2—N1118.3 (2)H153—C15—H151109.5
C12—C11—C1115.1 (3)C13—C15—H152109.5
C12—C11—H112108.5H153—C15—H152109.5
C1—C11—H112108.5H151—C15—H152109.5
C12—C11—H111108.5N2—C21—C22112.9 (3)
C1—C11—H111108.5N2—C21—H211109.0
H112—C11—H111107.5C22—C21—H211109.0
C11—C12—C13114.6 (3)N2—C21—H212109.0
C11—C12—H122108.6C22—C21—H212109.0
C13—C12—H122108.6H211—C21—H212107.8
C11—C12—H121108.6C21—C22—H223109.5
C13—C12—H121108.6C21—C22—H222109.5
H122—C12—H121107.6H223—C22—H222109.5
C12—C13—C15112.2 (5)C21—C22—H221109.5
C12—C13—C14110.0 (5)H223—C22—H221109.5
C15—C13—C14108.7 (6)H222—C22—H221109.5
C2—N1—C1—O12.1 (5)O1—C1—C11—C1254.6 (4)
C2—N1—C1—C11176.8 (3)N1—C1—C11—C12126.5 (3)
C21—N2—C2—O20.1 (4)C1—C11—C12—C1366.9 (5)
C21—N2—C2—N1178.8 (2)C11—C12—C13—C1563.1 (6)
C1—N1—C2—O2179.5 (3)C11—C12—C13—C14175.7 (5)
C1—N1—C2—N20.8 (4)C2—N2—C21—C2282.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.403.085 (3)137
N1—H11···O2ii0.862.002.861 (3)178
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl360K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.091 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.7564 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.5792 (14) ÅCell parameters from 2770 reflections
c = 5.1472 (6) Åθ = 2.8–27.3°
α = 90.683 (10)°µ = 0.08 mm1
β = 90.707 (6)°T = 360 K
γ = 89.216 (6)°Plate, colourless
V = 566.82 (13) Å31.00 × 1.00 × 0.20 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 27.4°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
6442 measured reflectionsl = 66
2389 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.100Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.316H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.1605P)2 + 0.2211P]
where P = (Fo2 + 2Fc2)/3
2389 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.31 e Å3
5 restraintsΔρmin = 0.29 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.4323 (3)0.5741 (2)0.2286 (6)0.0901 (8)
O20.0268 (3)0.4099 (2)0.2428 (5)0.0870 (8)
N10.1970 (3)0.5334 (2)0.3761 (6)0.0710 (8)
H110.13040.55210.48980.085*
N20.2524 (3)0.4167 (2)0.0336 (6)0.0747 (8)
H210.33850.44830.02050.090*
C10.3288 (4)0.5898 (3)0.3835 (7)0.0698 (9)
C20.1541 (4)0.4501 (3)0.2124 (7)0.0712 (9)
C110.3405 (5)0.6718 (3)0.5965 (8)0.0845 (10)
H1120.41880.64860.71900.101*
H1110.24430.67430.68810.101*
C120.3769 (6)0.7824 (4)0.5126 (11)0.1170 (16)
H1210.46920.77950.41040.140*
H1220.39790.82540.66620.140*
C130.2526 (7)0.8365 (4)0.3553 (13)0.140 (2)
H1310.22930.79220.20240.168*
C140.3085 (14)0.9442 (5)0.264 (2)0.233 (5)
H1430.22990.97820.16220.279*
H1420.39820.93400.16100.279*
H1410.33270.98810.41270.279*
C150.1069 (8)0.8536 (7)0.509 (2)0.218 (5)
H1530.03100.88770.40200.261*
H1510.12810.89770.65880.261*
H1520.06990.78620.56500.261*
C210.2183 (4)0.3289 (3)0.1393 (8)0.0845 (10)
H2110.27800.33560.29560.101*
H2120.11130.33310.18950.101*
C220.2504 (7)0.2222 (4)0.0241 (11)0.1191 (16)
H2230.22520.16760.14860.143*
H2220.18990.21410.12850.143*
H2210.35670.21650.02200.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0673 (14)0.1010 (18)0.1031 (18)0.0140 (12)0.0296 (13)0.0023 (14)
O20.0617 (14)0.0968 (17)0.1034 (19)0.0135 (11)0.0254 (12)0.0052 (14)
N10.0581 (14)0.0739 (16)0.0816 (17)0.0041 (11)0.0225 (12)0.0009 (13)
N20.0576 (14)0.0799 (17)0.0870 (19)0.0035 (12)0.0198 (13)0.0010 (14)
C10.0573 (16)0.0748 (19)0.078 (2)0.0007 (13)0.0135 (14)0.0148 (15)
C20.0556 (16)0.0758 (19)0.083 (2)0.0048 (13)0.0173 (14)0.0131 (16)
C110.079 (2)0.080 (2)0.095 (3)0.0000 (17)0.0101 (19)0.0035 (19)
C120.110 (3)0.106 (3)0.135 (4)0.014 (3)0.026 (3)0.008 (3)
C130.162 (6)0.111 (4)0.148 (5)0.011 (4)0.020 (4)0.018 (3)
C140.371 (16)0.107 (5)0.222 (9)0.005 (6)0.024 (10)0.049 (5)
C150.125 (6)0.169 (7)0.357 (14)0.028 (5)0.041 (8)0.009 (8)
C210.068 (2)0.093 (2)0.093 (2)0.0001 (17)0.0115 (18)0.004 (2)
C220.129 (4)0.089 (3)0.139 (4)0.004 (3)0.012 (3)0.004 (3)
Geometric parameters (Å, º) top
O1—C11.227 (4)C13—C151.522 (11)
O2—C21.243 (4)C13—C141.527 (10)
N1—C11.363 (4)C13—H1310.9800
N1—C21.390 (5)C14—H1430.9600
N1—H110.8600C14—H1420.9600
N2—C21.328 (4)C14—H1410.9600
N2—C211.443 (5)C15—H1530.9600
N2—H210.8600C15—H1510.9600
C1—C111.499 (5)C15—H1520.9600
C11—C121.502 (6)C21—C221.495 (6)
C11—H1120.9700C21—H2110.9700
C11—H1110.9700C21—H2120.9700
C12—C131.508 (8)C22—H2230.9600
C12—H1210.9700C22—H2220.9600
C12—H1220.9700C22—H2210.9600
C1—N1—C2129.7 (3)C12—C13—H131108.7
C1—N1—H11115.2C15—C13—H131108.7
C2—N1—H11115.2C14—C13—H131108.7
C2—N2—C21121.6 (3)C13—C14—H143109.5
C2—N2—H21119.2C13—C14—H142109.5
C21—N2—H21119.2H143—C14—H142109.5
O1—C1—N1122.5 (3)C13—C14—H141109.5
O1—C1—C11121.9 (3)H143—C14—H141109.5
N1—C1—C11115.6 (3)H142—C14—H141109.5
O2—C2—N2123.4 (3)C13—C15—H153109.5
O2—C2—N1118.4 (3)C13—C15—H151109.5
N2—C2—N1118.2 (3)H153—C15—H151109.5
C1—C11—C12115.9 (3)C13—C15—H152109.5
C1—C11—H112108.3H153—C15—H152109.5
C12—C11—H112108.3H151—C15—H152109.5
C1—C11—H111108.3N2—C21—C22113.8 (4)
C12—C11—H111108.3N2—C21—H211108.8
H112—C11—H111107.4C22—C21—H211108.8
C11—C12—C13114.7 (4)N2—C21—H212108.8
C11—C12—H121108.6C22—C21—H212108.8
C13—C12—H121108.6H211—C21—H212107.7
C11—C12—H122108.6C21—C22—H223109.5
C13—C12—H122108.6C21—C22—H222109.5
H121—C12—H122107.6H223—C22—H222109.5
C12—C13—C15112.3 (6)C21—C22—H221109.5
C12—C13—C14109.5 (6)H223—C22—H221109.5
C15—C13—C14108.9 (7)H222—C22—H221109.5
C2—N1—C1—O12.1 (6)O1—C1—C11—C1254.4 (5)
C2—N1—C1—C11177.0 (3)N1—C1—C11—C12126.5 (4)
C21—N2—C2—O20.7 (5)C1—C11—C12—C1367.5 (6)
C21—N2—C2—N1178.3 (3)C11—C12—C13—C1563.5 (7)
C1—N1—C2—O2179.6 (3)C11—C12—C13—C14175.5 (6)
C1—N1—C2—N20.5 (5)C2—N2—C21—C2282.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.413.092 (4)137
N1—H11···O2ii0.862.012.867 (3)178
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl362K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.104 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.670 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.5515 (9) ÅCell parameters from 2412 reflections
c = 5.1490 (5) Åθ = 2.8–27.4°
α = 90.036 (7)°µ = 0.08 mm1
β = 91.078 (4)°T = 362 K
γ = 88.834 (4)°Plate, colourless
V = 560.11 (9) Å31.00 × 1.00 × 0.20 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1478 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
6484 measured reflectionsl = 66
2361 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.094Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.332H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1819P)2 + 0.158P]
where P = (Fo2 + 2Fc2)/3
2361 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.37 e Å3
5 restraintsΔρmin = 0.34 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.4317 (3)0.5740 (2)0.2258 (5)0.0949 (9)
O20.0275 (3)0.4100 (2)0.2453 (5)0.0914 (9)
N10.1969 (3)0.5334 (2)0.3743 (6)0.0748 (8)
H110.12950.55240.48680.090*
N20.2531 (3)0.4165 (2)0.0370 (6)0.0797 (9)
H210.34050.44710.02540.096*
C10.3285 (3)0.5898 (3)0.3805 (7)0.0746 (9)
C20.1545 (4)0.4502 (3)0.2152 (7)0.0743 (9)
C110.3404 (5)0.6710 (3)0.5935 (8)0.0920 (11)
H1120.41980.64710.71660.110*
H1110.24340.67360.68450.110*
C120.3768 (6)0.7819 (4)0.5084 (11)0.1242 (17)
H1210.39850.82460.66150.149*
H1220.46970.77890.40640.149*
C130.2523 (8)0.8363 (4)0.3527 (13)0.152 (2)
H1310.22810.79230.20060.183*
C140.3107 (14)0.9435 (6)0.260 (2)0.251 (6)
H1430.23180.97870.15630.301*
H1420.40100.93220.15770.301*
H1410.33580.98700.40750.301*
C150.1059 (8)0.8539 (7)0.507 (2)0.227 (5)
H1530.02870.88870.39910.273*
H1510.12800.89760.65550.273*
H1520.06860.78640.56350.273*
C210.2176 (4)0.3298 (3)0.1379 (8)0.0913 (11)
H2110.27790.33650.29360.110*
H2120.10940.33460.18870.110*
C220.2508 (6)0.2234 (4)0.0178 (11)0.1232 (16)
H2230.22540.16840.13990.148*
H2220.19000.21590.13480.148*
H2210.35830.21760.02910.148*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0658 (13)0.1088 (19)0.1116 (19)0.0130 (12)0.0314 (13)0.0022 (14)
O20.0629 (13)0.0996 (17)0.1131 (19)0.0112 (11)0.0291 (12)0.0031 (14)
N10.0582 (14)0.0805 (17)0.0866 (17)0.0030 (11)0.0229 (12)0.0022 (13)
N20.0590 (14)0.0865 (18)0.0943 (19)0.0009 (12)0.0211 (13)0.0013 (15)
C10.0584 (15)0.0772 (19)0.089 (2)0.0043 (13)0.0159 (14)0.0167 (16)
C20.0570 (15)0.0818 (19)0.085 (2)0.0020 (13)0.0165 (14)0.0119 (16)
C110.080 (2)0.089 (2)0.107 (3)0.0002 (18)0.0159 (19)0.000 (2)
C120.117 (4)0.109 (3)0.148 (4)0.010 (3)0.034 (3)0.007 (3)
C130.177 (6)0.112 (4)0.166 (6)0.012 (4)0.020 (5)0.023 (4)
C140.389 (17)0.115 (5)0.250 (11)0.002 (7)0.047 (11)0.062 (6)
C150.129 (6)0.163 (7)0.387 (15)0.039 (5)0.026 (8)0.019 (8)
C210.072 (2)0.100 (3)0.102 (3)0.0020 (18)0.0164 (18)0.004 (2)
C220.129 (4)0.096 (3)0.144 (4)0.005 (3)0.010 (3)0.003 (3)
Geometric parameters (Å, º) top
O1—C11.222 (4)C13—C151.522 (11)
O2—C21.232 (4)C13—C141.527 (11)
N1—C11.355 (4)C13—H1310.9800
N1—C21.378 (5)C14—H1430.9600
N1—H110.8600C14—H1420.9600
N2—C21.329 (4)C14—H1410.9600
N2—C211.447 (5)C15—H1530.9600
N2—H210.8600C15—H1510.9600
C1—C111.500 (5)C15—H1520.9600
C11—C121.501 (6)C21—C221.492 (6)
C11—H1120.9700C21—H2110.9700
C11—H1110.9700C21—H2120.9700
C12—C131.487 (8)C22—H2230.9600
C12—H1210.9700C22—H2220.9600
C12—H1220.9700C22—H2210.9600
C1—N1—C2129.8 (3)C12—C13—H131108.7
C1—N1—H11115.1C15—C13—H131108.7
C2—N1—H11115.1C14—C13—H131108.7
C2—N2—C21121.9 (3)C13—C14—H143109.5
C2—N2—H21119.0C13—C14—H142109.5
C21—N2—H21119.0H143—C14—H142109.5
O1—C1—N1122.1 (4)C13—C14—H141109.5
O1—C1—C11122.4 (3)H143—C14—H141109.5
N1—C1—C11115.5 (3)H142—C14—H141109.5
O2—C2—N2122.9 (4)C13—C15—H153109.5
O2—C2—N1118.7 (3)C13—C15—H151109.5
N2—C2—N1118.4 (3)H153—C15—H151109.5
C1—C11—C12115.6 (4)C13—C15—H152109.5
C1—C11—H112108.4H153—C15—H152109.5
C12—C11—H112108.4H151—C15—H152109.5
C1—C11—H111108.4N2—C21—C22112.2 (4)
C12—C11—H111108.4N2—C21—H211109.2
H112—C11—H111107.4C22—C21—H211109.2
C13—C12—C11114.7 (4)N2—C21—H212109.2
C13—C12—H121108.6C22—C21—H212109.2
C11—C12—H121108.6H211—C21—H212107.9
C13—C12—H122108.6C21—C22—H223109.5
C11—C12—H122108.6C21—C22—H222109.5
H121—C12—H122107.6H223—C22—H222109.5
C12—C13—C15112.3 (6)C21—C22—H221109.5
C12—C13—C14108.8 (7)H223—C22—H221109.5
C15—C13—C14109.5 (7)H222—C22—H221109.5
C2—N1—C1—O12.6 (5)O1—C1—C11—C1254.3 (5)
C2—N1—C1—C11175.9 (3)N1—C1—C11—C12127.2 (4)
C21—N2—C2—O20.6 (5)C1—C11—C12—C1367.6 (6)
C21—N2—C2—N1179.9 (3)C11—C12—C13—C1563.7 (8)
C1—N1—C2—O2179.7 (3)C11—C12—C13—C14175.0 (6)
C1—N1—C2—N20.2 (5)C2—N2—C21—C2283.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.393.077 (4)137
N1—H11···O2ii0.862.012.866 (3)178
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl364K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.085 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.7109 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.6454 (10) ÅCell parameters from 2832 reflections
c = 5.1787 (6) Åθ = 2.8–27.5°
α = 90.134 (7)°µ = 0.08 mm1
β = 90.557 (4)°T = 364 K
γ = 88.953 (4)°Triclinic, p -1
V = 570.32 (11) Å31.00 × 1.00 × 0.20 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1474 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
7726 measured reflectionsl = 66
2503 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.091Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.301H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1424P)2 + 0.1845P]
where P = (Fo2 + 2Fc2)/3
2503 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.33 e Å3
5 restraintsΔρmin = 0.34 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.4319 (3)0.5736 (2)0.2249 (5)0.0986 (9)
O20.0272 (2)0.4103 (2)0.2467 (5)0.0946 (8)
N10.1969 (3)0.5332 (2)0.3748 (5)0.0782 (8)
H110.12990.55190.48790.094*
N20.2527 (3)0.4164 (2)0.0378 (5)0.0816 (8)
H210.33940.44730.02410.098*
C10.3282 (3)0.5898 (3)0.3795 (7)0.0773 (9)
C20.1543 (3)0.4501 (3)0.2157 (7)0.0770 (9)
C110.3393 (4)0.6712 (3)0.5878 (8)0.0947 (11)
H1120.41740.64780.71080.114*
H1110.24230.67410.67810.114*
C120.3765 (6)0.7815 (4)0.5040 (12)0.1366 (19)
H1210.39830.82360.65630.164*
H1220.46900.77840.40120.164*
C130.2526 (8)0.8360 (5)0.3510 (13)0.164 (2)
H1310.22780.79210.20050.197*
C140.3093 (14)0.9432 (6)0.256 (2)0.268 (6)
H1430.23000.97740.15450.321*
H1420.39880.93240.15160.321*
H1410.33450.98690.40130.321*
C150.1066 (9)0.8549 (7)0.506 (2)0.254 (5)
H1530.03110.89060.39980.305*
H1510.12940.89770.65420.305*
H1520.06740.78820.56120.305*
C210.2184 (4)0.3296 (3)0.1327 (8)0.0941 (11)
H2110.27850.33630.28830.113*
H2120.11080.33420.18210.113*
C220.2509 (6)0.2236 (4)0.0161 (11)0.1308 (17)
H2230.22560.16940.13850.157*
H2220.19020.21570.13620.157*
H2210.35790.21770.02910.157*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0688 (13)0.1134 (18)0.1148 (19)0.0135 (12)0.0318 (13)0.0016 (14)
O20.0659 (13)0.1035 (17)0.1153 (19)0.0122 (11)0.0291 (12)0.0042 (14)
N10.0613 (14)0.0823 (16)0.0916 (18)0.0019 (11)0.0244 (12)0.0028 (14)
N20.0597 (14)0.0895 (18)0.0961 (19)0.0029 (12)0.0200 (13)0.0002 (15)
C10.0602 (16)0.0814 (19)0.090 (2)0.0025 (13)0.0160 (14)0.0168 (16)
C20.0569 (15)0.086 (2)0.088 (2)0.0057 (14)0.0179 (14)0.0129 (17)
C110.083 (2)0.087 (2)0.115 (3)0.0018 (17)0.0169 (19)0.002 (2)
C120.124 (4)0.118 (4)0.169 (5)0.011 (3)0.040 (3)0.007 (3)
C130.175 (6)0.133 (4)0.183 (6)0.019 (4)0.013 (5)0.039 (4)
C140.416 (18)0.120 (5)0.268 (11)0.021 (7)0.024 (11)0.065 (6)
C150.138 (6)0.191 (8)0.432 (16)0.044 (5)0.026 (8)0.027 (9)
C210.073 (2)0.103 (3)0.106 (3)0.0018 (17)0.0162 (18)0.001 (2)
C220.135 (4)0.100 (3)0.157 (4)0.007 (3)0.013 (3)0.001 (3)
Geometric parameters (Å, º) top
O1—C11.226 (4)C13—C151.525 (11)
O2—C21.236 (4)C13—C141.536 (10)
N1—C11.360 (4)C13—H1310.9800
N1—C21.388 (5)C14—H1430.9600
N1—H110.8600C14—H1420.9600
N2—C21.329 (4)C14—H1410.9600
N2—C211.440 (5)C15—H1530.9600
N2—H210.8600C15—H1510.9600
C1—C111.494 (5)C15—H1520.9600
C11—C121.503 (6)C21—C221.493 (6)
C11—H1120.9700C21—H2110.9700
C11—H1110.9700C21—H2120.9700
C12—C131.492 (8)C22—H2230.9600
C12—H1210.9700C22—H2220.9600
C12—H1220.9700C22—H2210.9600
C1—N1—C2129.9 (3)C12—C13—H131108.6
C1—N1—H11115.0C15—C13—H131108.6
C2—N1—H11115.0C14—C13—H131108.6
C2—N2—C21121.9 (3)C13—C14—H143109.5
C2—N2—H21119.1C13—C14—H142109.5
C21—N2—H21119.1H143—C14—H142109.5
O1—C1—N1122.0 (3)C13—C14—H141109.5
O1—C1—C11122.3 (3)H143—C14—H141109.5
N1—C1—C11115.7 (3)H142—C14—H141109.5
O2—C2—N2123.0 (3)C13—C15—H153109.5
O2—C2—N1118.7 (3)C13—C15—H151109.5
N2—C2—N1118.3 (3)H153—C15—H151109.5
C1—C11—C12116.5 (4)C13—C15—H152109.5
C1—C11—H112108.2H153—C15—H152109.5
C12—C11—H112108.2H151—C15—H152109.5
C1—C11—H111108.2N2—C21—C22113.5 (4)
C12—C11—H111108.2N2—C21—H211108.9
H112—C11—H111107.3C22—C21—H211108.9
C13—C12—C11114.6 (4)N2—C21—H212108.9
C13—C12—H121108.6C22—C21—H212108.9
C11—C12—H121108.6H211—C21—H212107.7
C13—C12—H122108.6C21—C22—H223109.5
C11—C12—H122108.6C21—C22—H222109.5
H121—C12—H122107.6H223—C22—H222109.5
C12—C13—C15112.7 (6)C21—C22—H221109.5
C12—C13—C14109.7 (6)H223—C22—H221109.5
C15—C13—C14108.4 (7)H222—C22—H221109.5
C2—N1—C1—O11.9 (5)O1—C1—C11—C1253.8 (5)
C2—N1—C1—C11176.9 (3)N1—C1—C11—C12127.3 (4)
C21—N2—C2—O20.4 (5)C1—C11—C12—C1368.3 (6)
C21—N2—C2—N1179.1 (3)C11—C12—C13—C1564.2 (8)
C1—N1—C2—O2179.9 (3)C11—C12—C13—C14174.8 (6)
C1—N1—C2—N20.6 (5)C2—N2—C21—C2283.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.393.083 (3)137
N1—H11···O2ii0.862.002.860 (3)178
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl366K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.088 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.7157 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.6307 (7) ÅCell parameters from 2373 reflections
c = 5.1642 (7) Åθ = 2.8–27.4°
α = 89.78 (1)°µ = 0.08 mm1
β = 90.522 (6)°T = 366 K
γ = 88.757 (5)°Plate, colourless
V = 568.34 (11) Å31.00 × 1.00 × 0.20 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1377 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
6593 measured reflectionsl = 66
2383 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.100Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.342H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1637P)2 + 0.2294P]
where P = (Fo2 + 2Fc2)/3
2383 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.32 e Å3
5 restraintsΔρmin = 0.35 e Å3
Special details top

Experimental. The crystal was being low temperature phase.

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
O10.4312 (3)0.5736 (2)0.2226 (6)0.1031 (10)
O20.0275 (3)0.4105 (2)0.2482 (6)0.0982 (10)
N10.1970 (3)0.5329 (2)0.3746 (6)0.0805 (9)
H110.13070.55130.48920.097*
N20.2532 (3)0.4167 (2)0.0410 (7)0.0849 (10)
H210.34010.44710.02820.102*
C10.3274 (4)0.5894 (3)0.3763 (8)0.0797 (10)
C20.1540 (4)0.4501 (3)0.2168 (8)0.0822 (11)
C110.3390 (5)0.6702 (3)0.5821 (10)0.1012 (13)
H1110.41730.64650.70510.121*
H1120.24230.67330.67340.121*
C120.3760 (7)0.7804 (4)0.4976 (15)0.154 (3)
H1210.39920.82200.65000.185*
H1220.46750.77730.39220.185*
C130.2512 (9)0.8357 (6)0.3477 (17)0.176 (3)
H1310.22610.79260.19640.212*
C140.3096 (17)0.9424 (7)0.252 (3)0.299 (8)
H1430.23130.97750.14980.358*
H1420.39940.93090.14890.358*
H1410.33490.98570.39830.358*
C150.1057 (10)0.8541 (9)0.503 (3)0.271 (6)
H1530.02930.88890.39540.325*
H1510.12780.89770.64960.325*
H1520.06800.78740.56090.325*
C210.2180 (5)0.3301 (4)0.1300 (9)0.1003 (13)
H2110.27770.33650.28670.120*
H2120.11020.33480.17850.120*
C220.2515 (7)0.2241 (4)0.0079 (13)0.135 (2)
H2230.22600.16920.12770.162*
H2220.19150.21690.14590.162*
H2210.35860.21830.03630.162*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0734 (16)0.117 (2)0.120 (2)0.0134 (14)0.0366 (15)0.0011 (17)
O20.0680 (15)0.107 (2)0.121 (2)0.0110 (13)0.0309 (14)0.0051 (16)
N10.0627 (16)0.0837 (19)0.096 (2)0.0030 (13)0.0232 (14)0.0002 (16)
N20.0622 (16)0.092 (2)0.101 (2)0.0023 (14)0.0219 (15)0.0020 (17)
C10.0637 (18)0.082 (2)0.093 (2)0.0011 (15)0.0165 (17)0.0163 (18)
C20.0587 (17)0.091 (2)0.097 (3)0.0060 (16)0.0196 (17)0.016 (2)
C110.089 (3)0.089 (3)0.126 (4)0.001 (2)0.020 (2)0.004 (2)
C120.145 (5)0.119 (4)0.201 (7)0.007 (4)0.053 (5)0.008 (4)
C130.181 (7)0.140 (5)0.207 (8)0.017 (5)0.013 (6)0.043 (5)
C140.47 (2)0.117 (6)0.308 (15)0.035 (9)0.053 (15)0.050 (7)
C150.140 (8)0.223 (10)0.45 (2)0.056 (7)0.018 (10)0.008 (11)
C210.077 (2)0.113 (3)0.112 (3)0.000 (2)0.018 (2)0.004 (3)
C220.138 (5)0.102 (3)0.166 (5)0.004 (3)0.013 (4)0.004 (3)
Geometric parameters (Å, º) top
O1—C11.222 (4)C13—C151.520 (13)
O2—C21.233 (4)C13—C141.532 (13)
N1—C11.355 (5)C13—H1310.9800
N1—C21.385 (5)C14—H1430.9600
N1—H110.8600C14—H1420.9600
N2—C21.323 (5)C14—H1410.9600
N2—C211.445 (5)C15—H1530.9600
N2—H210.8600C15—H1510.9600
C1—C111.481 (6)C15—H1520.9600
C11—C121.499 (7)C21—C221.500 (7)
C11—H1110.9700C21—H2110.9700
C11—H1120.9700C21—H2120.9700
C12—C131.490 (10)C22—H2230.9600
C12—H1210.9700C22—H2220.9600
C12—H1220.9700C22—H2210.9600
C1—N1—C2129.9 (3)C12—C13—H131108.4
C1—N1—H11115.0C15—C13—H131108.4
C2—N1—H11115.0C14—C13—H131108.4
C2—N2—C21121.2 (3)C13—C14—H143109.5
C2—N2—H21119.4C13—C14—H142109.5
C21—N2—H21119.4H143—C14—H142109.5
O1—C1—N1122.6 (4)C13—C14—H141109.5
O1—C1—C11121.6 (4)H143—C14—H141109.5
N1—C1—C11115.7 (3)H142—C14—H141109.5
O2—C2—N2123.4 (4)C13—C15—H153109.5
O2—C2—N1118.9 (3)C13—C15—H151109.5
N2—C2—N1117.6 (3)H153—C15—H151109.5
C1—C11—C12116.8 (5)C13—C15—H152109.5
C1—C11—H111108.1H153—C15—H152109.5
C12—C11—H111108.1H151—C15—H152109.5
C1—C11—H112108.1N2—C21—C22112.4 (4)
C12—C11—H112108.1N2—C21—H211109.1
H111—C11—H112107.3C22—C21—H211109.1
C13—C12—C11114.5 (5)N2—C21—H212109.1
C13—C12—H121108.6C22—C21—H212109.1
C11—C12—H121108.6H211—C21—H212107.9
C13—C12—H122108.6C21—C22—H223109.5
C11—C12—H122108.6C21—C22—H222109.5
H121—C12—H122107.6H223—C22—H222109.5
C12—C13—C15113.4 (7)C21—C22—H221109.5
C12—C13—C14108.9 (8)H223—C22—H221109.5
C15—C13—C14109.2 (9)H222—C22—H221109.5
C2—N1—C1—O11.1 (6)O1—C1—C11—C1253.9 (6)
C2—N1—C1—C11177.2 (4)N1—C1—C11—C12127.7 (4)
C21—N2—C2—O20.4 (6)C1—C11—C12—C1369.0 (7)
C21—N2—C2—N1179.5 (3)C11—C12—C13—C1563.5 (10)
C1—N1—C2—O2179.3 (3)C11—C12—C13—C14174.6 (7)
C1—N1—C2—N21.6 (6)C2—N2—C21—C2283.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.403.085 (4)137
N1—H11···O2ii0.862.002.855 (4)178
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl368K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.081 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.6912 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.7757 (6) ÅCell parameters from 2775 reflections
c = 5.1587 (1) Åθ = 2.8–27.5°
α = 88.386 (2)°µ = 0.08 mm1
β = 91.168 (6)°T = 368 K
γ = 88.4630 (19)°Plate, colourless
V = 572.24 (4) Å31.00 × 1.00 × 0.20 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1212 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
7417 measured reflectionsl = 66
2283 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.099Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.308H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1263P)2 + 0.2311P]
where P = (Fo2 + 2Fc2)/3
2283 reflections(Δ/σ)max < 0.001
131 parametersΔρmax = 0.24 e Å3
17 restraintsΔρmin = 0.28 e Å3
Special details top

Experimental. The crystal was being high temperature phase.

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*/UeqOcc. (<1)
O10.4310 (3)0.5728 (2)0.2201 (6)0.1095 (11)
O20.0279 (3)0.4107 (2)0.2539 (6)0.1050 (10)
N10.1966 (3)0.5326 (2)0.3729 (6)0.0858 (10)
H110.13020.55130.48520.103*
N20.2532 (3)0.4167 (3)0.0458 (7)0.0928 (10)
H210.34030.44660.03290.111*
C10.3272 (4)0.5884 (3)0.3710 (7)0.0866 (11)
C20.1542 (4)0.4496 (3)0.2198 (8)0.0861 (11)
C11A0.3370 (5)0.6696 (3)0.5749 (9)0.1098 (14)0.874 (6)
H1110.41380.64540.70350.132*0.874 (6)
H1120.23880.67290.66090.132*0.874 (6)
C12A0.3760 (7)0.7806 (4)0.4893 (15)0.158 (3)0.874 (6)
H1210.46710.77820.38390.190*0.874 (6)
H1220.39930.82080.64120.190*0.874 (6)
C13A0.2445 (9)0.8353 (6)0.3344 (16)0.179 (4)0.874 (6)
H1310.21670.79410.18390.214*0.874 (6)
C14A0.3006 (18)0.9430 (6)0.245 (3)0.288 (8)0.874 (6)
H1420.38860.93400.13730.433*0.874 (6)
H1410.32860.98240.39350.433*0.874 (6)
H1430.21980.97990.14770.433*0.874 (6)
C15A0.1029 (11)0.8553 (9)0.500 (3)0.265 (6)0.874 (6)
H1530.02260.88870.39400.397*0.874 (6)
H1510.12960.89980.63940.397*0.874 (6)
H1520.06780.78980.56880.397*0.874 (6)
C11B0.3370 (5)0.6696 (3)0.5749 (9)0.1098 (14)0.126 (6)
H1130.44140.69430.58640.132*0.126 (6)
H1140.31200.63850.74190.132*0.126 (6)
C12B0.226 (2)0.7623 (11)0.511 (5)0.158 (3)0.126 (6)
H1230.18570.75490.33630.190*0.126 (6)
H1240.14000.75810.62760.190*0.126 (6)
C13B0.293 (4)0.8711 (8)0.531 (7)0.179 (4)0.126 (6)
H1320.20950.92330.50350.214*0.126 (6)
C14B0.411 (8)0.888 (4)0.317 (11)0.288 (8)0.126 (6)
H1440.45240.95660.33030.433*0.126 (6)
H1450.36110.88190.15070.433*0.126 (6)
H1460.49250.83610.33710.433*0.126 (6)
C15B0.368 (6)0.888 (3)0.797 (10)0.265 (6)0.126 (6)
H1540.37930.96110.82220.397*0.126 (6)
H1550.46670.85260.80760.397*0.126 (6)
H1560.30310.85930.92950.397*0.126 (6)
C210.2181 (5)0.3309 (3)0.1245 (9)0.1067 (14)
H2110.27720.33840.28110.128*
H2120.10990.33580.17420.128*
C220.2527 (7)0.2252 (4)0.0027 (12)0.145 (2)
H2230.22590.17220.12250.174*
H2220.19400.21690.15170.174*
H2210.36050.21870.04090.174*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0768 (16)0.125 (2)0.129 (2)0.0137 (14)0.0384 (16)0.0026 (18)
O20.0712 (16)0.116 (2)0.129 (2)0.0131 (14)0.0339 (15)0.0055 (17)
N10.0638 (16)0.091 (2)0.103 (2)0.0010 (14)0.0245 (15)0.0014 (18)
N20.0661 (17)0.104 (2)0.109 (2)0.0023 (15)0.0234 (16)0.0014 (19)
C10.068 (2)0.085 (2)0.106 (3)0.0029 (17)0.0175 (19)0.017 (2)
C20.0628 (19)0.092 (2)0.102 (3)0.0040 (17)0.0193 (19)0.016 (2)
C11A0.092 (3)0.099 (3)0.139 (4)0.001 (2)0.022 (3)0.004 (3)
C12A0.151 (6)0.120 (5)0.209 (8)0.018 (4)0.075 (6)0.013 (5)
C13A0.201 (9)0.152 (7)0.178 (8)0.009 (6)0.019 (7)0.049 (6)
C14A0.48 (2)0.098 (6)0.287 (14)0.008 (8)0.042 (14)0.056 (7)
C15A0.151 (8)0.209 (10)0.432 (19)0.052 (7)0.029 (10)0.005 (11)
C11B0.092 (3)0.099 (3)0.139 (4)0.001 (2)0.022 (3)0.004 (3)
C12B0.151 (6)0.120 (5)0.209 (8)0.018 (4)0.075 (6)0.013 (5)
C13B0.201 (9)0.152 (7)0.178 (8)0.009 (6)0.019 (7)0.049 (6)
C14B0.48 (2)0.098 (6)0.287 (14)0.008 (8)0.042 (14)0.056 (7)
C15B0.151 (8)0.209 (10)0.432 (19)0.052 (7)0.029 (10)0.005 (11)
C210.085 (3)0.113 (3)0.123 (3)0.002 (2)0.021 (2)0.000 (3)
C220.150 (5)0.115 (4)0.169 (5)0.005 (3)0.017 (4)0.000 (4)
Geometric parameters (Å, º) top
O1—C11.219 (4)C15A—H1530.9600
O2—C21.231 (4)C15A—H1510.9600
N1—C11.356 (5)C15A—H1520.9600
N1—C21.393 (5)C12B—C13B1.53 (2)
N1—H110.8600C12B—H1230.9700
N2—C21.326 (5)C12B—H1240.9700
N2—C211.459 (6)C13B—C15B1.53 (6)
N2—H210.8600C13B—C14B1.53 (7)
C1—C11A1.501 (6)C13B—H1320.9800
C11A—C12A1.522 (6)C14B—H1440.9600
C11A—H1110.9700C14B—H1450.9600
C11A—H1120.9700C14B—H1460.9600
C11A—C12B1.530 (18)C15B—H1540.9600
C12A—C13A1.524 (10)C15B—H1550.9600
C12A—H1210.9700C15B—H1560.9600
C12A—H1220.9700C21—C221.493 (7)
C13A—C15A1.531 (14)C21—H2110.9700
C13A—C14A1.533 (12)C21—H2120.9700
C13A—H1310.9800C22—H2230.9600
C14A—H1420.9600C22—H2220.9600
C14A—H1410.9600C22—H2210.9600
C14A—H1430.9600
C1—N1—C2129.5 (3)H153—C15A—H151109.5
C1—N1—H11115.2C13A—C15A—H152109.5
C2—N1—H11115.2H153—C15A—H152109.5
C2—N2—C21121.6 (3)H151—C15A—H152109.5
C2—N2—H21119.2C13B—C12B—H123108.3
C21—N2—H21119.2C13B—C12B—H124108.3
O1—C1—N1123.1 (4)H123—C12B—H124107.4
O1—C1—C11A122.0 (4)C12B—C13B—C15B111.8 (7)
N1—C1—C11A114.8 (3)C12B—C13B—C14B109.9 (7)
O2—C2—N2123.7 (4)C15B—C13B—C14B110.4 (7)
O2—C2—N1118.5 (3)C12B—C13B—H132108.2
N2—C2—N1117.8 (3)C15B—C13B—H132108.2
C1—C11A—C12A118.0 (4)C14B—C13B—H132108.2
C1—C11A—H111107.8C13B—C14B—H144109.5
C12A—C11A—H111107.8C13B—C14B—H145109.5
C1—C11A—H112107.8H144—C14B—H145109.5
C12A—C11A—H112107.8C13B—C14B—H146109.5
H111—C11A—H112107.2H144—C14B—H146109.5
C11A—C12A—C13A112.2 (5)H145—C14B—H146109.5
C11A—C12A—H121109.2C13B—C15B—H154109.5
C13A—C12A—H121109.2C13B—C15B—H155109.5
C11A—C12A—H122109.2H154—C15B—H155109.5
C13A—C12A—H122109.2C13B—C15B—H156109.5
H121—C12A—H122107.9H154—C15B—H156109.5
C12A—C13A—C15A112.2 (7)H155—C15B—H156109.5
C12A—C13A—C14A107.4 (7)N2—C21—C22113.3 (4)
C15A—C13A—C14A106.7 (10)N2—C21—H211108.9
C12A—C13A—H131110.1C22—C21—H211108.9
C15A—C13A—H131110.1N2—C21—H212108.9
C14A—C13A—H131110.1C22—C21—H212108.9
C13A—C14A—H142109.5H211—C21—H212107.7
C13A—C14A—H141109.5C21—C22—H223109.5
H142—C14A—H141109.5C21—C22—H222109.5
C13A—C14A—H143109.5H223—C22—H222109.5
H142—C14A—H143109.5C21—C22—H221109.5
H141—C14A—H143109.5H223—C22—H221109.5
C13A—C15A—H153109.5H222—C22—H221109.5
C13A—C15A—H151109.5
C2—N1—C1—O11.4 (6)C11A—C12A—C13A—C15A66.5 (9)
C2—N1—C1—C11A177.0 (4)C11A—C12A—C13A—C14A176.5 (7)
C21—N2—C2—O20.9 (6)C2—N2—C21—C2284.0 (5)
C21—N2—C2—N1179.4 (3)C2—N1—C1—C11B177.0 (4)
C1—N1—C2—O2179.4 (4)O1—C1—C11B—C12B109.5 (13)
C1—N1—C2—N20.9 (6)N1—C1—C11B—C12B72.0 (13)
O1—C1—C11A—C12A52.5 (6)C1—C11B—C12B—C13B132.0 (18)
N1—C1—C11A—C12A129.1 (5)C11B—C12B—C13B—C15B55 (3)
C1—C11A—C12A—C13A70.6 (7)C11B—C12B—C13B—C14B68 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.413.098 (4)137
N1—H11···O2ii0.862.002.863 (4)178
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl370K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.084 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.605 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.855 (2) ÅCell parameters from 2605 reflections
c = 5.1699 (10) Åθ = 2.9–27.5°
α = 87.263 (16)°µ = 0.08 mm1
β = 92.266 (9)°T = 370 K
γ = 88.060 (8)°Plate, colourless
V = 570.39 (19) Å31.00 × 1.00 × 0.20 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
9055 measured reflectionsl = 66
2263 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.116Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.386H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1627P)2 + 0.2588P]
where P = (Fo2 + 2Fc2)/3
2263 reflections(Δ/σ)max < 0.001
131 parametersΔρmax = 0.28 e Å3
17 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. The crystal was being high temperature phase.

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*/UeqOcc. (<1)
O10.4305 (4)0.5716 (3)0.2153 (8)0.1207 (14)
O20.0278 (4)0.4110 (3)0.2582 (8)0.1167 (14)
N10.1965 (4)0.5326 (3)0.3720 (8)0.0955 (13)
H110.13050.55080.48360.115*
N20.2530 (4)0.4165 (3)0.0519 (8)0.1012 (14)
H210.34060.44610.03750.121*
C10.3268 (5)0.5873 (4)0.3646 (10)0.0971 (15)
C20.1552 (5)0.4504 (4)0.2223 (11)0.0985 (15)
C11A0.3352 (7)0.6690 (4)0.5612 (11)0.124 (2)0.813 (8)
H1110.41210.64500.69490.148*0.813 (8)
H1120.23550.67280.64200.148*0.813 (8)
C12A0.3745 (11)0.7794 (5)0.472 (2)0.177 (4)0.813 (8)
H1210.46540.77670.36660.212*0.813 (8)
H1220.39970.81910.62160.212*0.813 (8)
C13A0.2393 (13)0.8341 (8)0.314 (2)0.190 (5)0.813 (8)
H1310.20890.79400.16490.228*0.813 (8)
C14A0.292 (3)0.9422 (9)0.226 (4)0.333 (12)0.813 (8)
H1420.38050.93480.11910.499*0.813 (8)
H1410.32100.98020.37480.499*0.813 (8)
H1430.20900.97930.12830.499*0.813 (8)
C15A0.0990 (16)0.8579 (13)0.477 (4)0.307 (10)0.813 (8)
H1530.01740.89200.36910.461*0.813 (8)
H1510.12910.90260.61260.461*0.813 (8)
H1520.06230.79400.55250.461*0.813 (8)
C11B0.3352 (7)0.6690 (4)0.5612 (11)0.124 (2)0.187 (8)
H1130.44080.69260.57740.148*0.187 (8)
H1140.30770.63930.72860.148*0.187 (8)
C12B0.224 (2)0.7617 (10)0.482 (5)0.177 (4)0.187 (8)
H1230.18950.75510.30290.212*0.187 (8)
H1240.13360.75720.58660.212*0.187 (8)
C13B0.290 (4)0.8698 (8)0.507 (7)0.190 (5)0.187 (8)
H1320.20340.92120.49140.228*0.187 (8)
C14B0.399 (8)0.893 (4)0.286 (10)0.333 (12)0.187 (8)
H1440.43860.96160.30130.499*0.187 (8)
H1450.34280.88970.12300.499*0.187 (8)
H1460.48430.84270.29570.499*0.187 (8)
C15B0.376 (5)0.881 (3)0.769 (9)0.307 (10)0.187 (8)
H1540.39040.95330.79590.461*0.187 (8)
H1550.47490.84450.77070.461*0.187 (8)
H1560.31480.85180.90440.461*0.187 (8)
C210.2180 (6)0.3318 (4)0.1106 (12)0.1171 (19)
H2110.27760.33840.26560.140*
H2120.10850.33710.16380.140*
C220.2534 (9)0.2264 (5)0.0197 (17)0.167 (3)
H2230.22720.17340.09750.200*
H2220.19340.21870.17170.200*
H2210.36220.21980.06840.200*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.080 (2)0.146 (3)0.139 (3)0.0148 (19)0.037 (2)0.006 (2)
O20.077 (2)0.129 (3)0.147 (3)0.0122 (18)0.034 (2)0.011 (2)
N10.070 (2)0.100 (3)0.117 (3)0.0018 (19)0.025 (2)0.001 (2)
N20.071 (2)0.114 (3)0.120 (3)0.003 (2)0.023 (2)0.004 (3)
C10.070 (3)0.098 (3)0.123 (4)0.000 (2)0.017 (3)0.008 (3)
C20.062 (2)0.114 (4)0.119 (4)0.005 (2)0.027 (2)0.016 (3)
C11A0.095 (4)0.110 (4)0.166 (6)0.002 (3)0.021 (3)0.002 (4)
C12A0.168 (9)0.138 (7)0.231 (11)0.024 (6)0.088 (9)0.000 (7)
C13A0.191 (11)0.173 (9)0.197 (12)0.007 (8)0.029 (9)0.054 (9)
C14A0.54 (4)0.117 (9)0.34 (2)0.007 (13)0.04 (2)0.053 (11)
C15A0.143 (11)0.246 (16)0.53 (3)0.046 (10)0.048 (14)0.045 (17)
C11B0.095 (4)0.110 (4)0.166 (6)0.002 (3)0.021 (3)0.002 (4)
C12B0.168 (9)0.138 (7)0.231 (11)0.024 (6)0.088 (9)0.000 (7)
C13B0.191 (11)0.173 (9)0.197 (12)0.007 (8)0.029 (9)0.054 (9)
C14B0.54 (4)0.117 (9)0.34 (2)0.007 (13)0.04 (2)0.053 (11)
C15B0.143 (11)0.246 (16)0.53 (3)0.046 (10)0.048 (14)0.045 (17)
C210.088 (3)0.125 (4)0.138 (5)0.006 (3)0.016 (3)0.004 (4)
C220.153 (7)0.126 (5)0.222 (9)0.008 (5)0.020 (6)0.018 (6)
Geometric parameters (Å, º) top
O1—C11.221 (6)C15A—H1530.9600
O2—C21.241 (6)C15A—H1510.9600
N1—C11.345 (6)C15A—H1520.9600
N1—C21.386 (7)C12B—C13B1.53 (2)
N1—H110.8600C12B—H1230.9700
N2—C21.321 (6)C12B—H1240.9700
N2—C211.440 (7)C13B—C15B1.53 (6)
N2—H210.8600C13B—C14B1.53 (7)
C1—C11A1.497 (7)C13B—H1320.9800
C11A—C12A1.525 (9)C14B—H1440.9600
C11A—H1110.9700C14B—H1450.9600
C11A—H1120.9700C14B—H1460.9600
C11A—C12B1.530 (17)C15B—H1540.9600
C12A—C13A1.526 (14)C15B—H1550.9600
C12A—H1210.9700C15B—H1560.9600
C12A—H1220.9700C21—C221.500 (9)
C13A—C15A1.53 (2)C21—H2110.9700
C13A—C14A1.532 (18)C21—H2120.9700
C13A—H1310.9800C22—H2230.9600
C14A—H1420.9600C22—H2220.9600
C14A—H1410.9600C22—H2210.9600
C14A—H1430.9600
C1—N1—C2128.1 (4)H153—C15A—H151109.5
C1—N1—H11115.9C13A—C15A—H152109.5
C2—N1—H11115.9H153—C15A—H152109.5
C2—N2—C21122.3 (4)H151—C15A—H152109.5
C2—N2—H21118.9C13B—C12B—H123108.2
C21—N2—H21118.9C13B—C12B—H124108.2
O1—C1—N1123.7 (5)H123—C12B—H124107.4
O1—C1—C11A122.6 (5)C12B—C13B—C15B112.2 (7)
N1—C1—C11A113.7 (4)C12B—C13B—C14B109.9 (7)
O2—C2—N2122.9 (6)C15B—C13B—C14B110.3 (7)
O2—C2—N1117.9 (4)C12B—C13B—H132108.1
N2—C2—N1119.2 (4)C15B—C13B—H132108.1
C1—C11A—C12A118.6 (6)C14B—C13B—H132108.1
C1—C11A—H111107.7C13B—C14B—H144109.5
C12A—C11A—H111107.7C13B—C14B—H145109.5
C1—C11A—H112107.7H144—C14B—H145109.5
C12A—C11A—H112107.7C13B—C14B—H146109.5
H111—C11A—H112107.1H144—C14B—H146109.5
C11A—C12A—C13A111.5 (7)H145—C14B—H146109.5
C11A—C12A—H121109.3C13B—C15B—H154109.5
C13A—C12A—H121109.3C13B—C15B—H155109.5
C11A—C12A—H122109.3H154—C15B—H155109.5
C13A—C12A—H122109.3C13B—C15B—H156109.5
H121—C12A—H122108.0H154—C15B—H156109.5
C12A—C13A—C15A112.9 (10)H155—C15B—H156109.5
C12A—C13A—C14A107.4 (11)N2—C21—C22113.4 (5)
C15A—C13A—C14A103.6 (14)N2—C21—H211108.9
C12A—C13A—H131110.9C22—C21—H211108.9
C15A—C13A—H131110.9N2—C21—H212108.9
C14A—C13A—H131110.9C22—C21—H212108.9
C13A—C14A—H142109.5H211—C21—H212107.7
C13A—C14A—H141109.5C21—C22—H223109.5
H142—C14A—H141109.5C21—C22—H222109.5
C13A—C14A—H143109.5H223—C22—H222109.5
H142—C14A—H143109.5C21—C22—H221109.5
H141—C14A—H143109.5H223—C22—H221109.5
C13A—C15A—H153109.5H222—C22—H221109.5
C13A—C15A—H151109.5
C2—N1—C1—O10.7 (8)C11A—C12A—C13A—C15A68.4 (13)
C2—N1—C1—C11A178.1 (5)C11A—C12A—C13A—C14A178.0 (11)
C21—N2—C2—O21.3 (8)C2—N2—C21—C2283.3 (6)
C21—N2—C2—N1179.8 (5)C2—N1—C1—C11B178.1 (5)
C1—N1—C2—O2179.2 (4)O1—C1—C11B—C12B107.1 (13)
C1—N1—C2—N21.8 (8)N1—C1—C11B—C12B74.1 (12)
O1—C1—C11A—C12A50.8 (8)C1—C11B—C12B—C13B134.6 (18)
N1—C1—C11A—C12A130.3 (6)C11B—C12B—C13B—C15B47 (3)
C1—C11A—C12A—C13A72.2 (10)C11B—C12B—C13B—C14B76 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.423.107 (5)138
N1—H11···O2ii0.862.012.870 (5)178
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl372K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.068 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.6137 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.994 (3) ÅCell parameters from 2962 reflections
c = 5.1906 (11) Åθ = 2.8–27.5°
α = 86.197 (10)°µ = 0.08 mm1
β = 91.616 (12)°T = 372 K
γ = 88.099 (6)°Plate, colourless
V = 579.1 (2) Å31.00 × 0.60 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1114 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 27.5°, θmin = 2.8°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
8178 measured reflectionsl = 66
2312 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.124Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.334H-atom parameters constrained
S = 1.75 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
2312 reflections(Δ/σ)max < 0.001
131 parametersΔρmax = 0.39 e Å3
17 restraintsΔρmin = 0.29 e Å3
Special details top

Experimental. The crystal was being high temperature phase.

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*/UeqOcc. (<1)
O10.4299 (3)0.5710 (2)0.2076 (6)0.1290 (10)
O20.0275 (2)0.41152 (19)0.2663 (5)0.1204 (9)
N10.1962 (3)0.5315 (2)0.3685 (6)0.1017 (9)
H110.13020.55010.47930.122*
N20.2536 (3)0.4159 (2)0.0604 (6)0.1066 (10)
H210.34190.44450.04640.128*
C10.3266 (4)0.5868 (2)0.3546 (7)0.1013 (11)
C20.1551 (4)0.4493 (3)0.2288 (7)0.1005 (10)
C11A0.3342 (5)0.6684 (2)0.5442 (8)0.1283 (14)0.774 (6)
H1110.40950.64490.67970.154*0.774 (6)
H1120.23380.67340.62350.154*0.774 (6)
C12A0.3760 (7)0.7768 (3)0.4458 (17)0.203 (4)0.774 (6)
H1210.41170.81430.59030.243*0.774 (6)
H1220.46060.77200.32730.243*0.774 (6)
C13A0.2389 (8)0.8363 (6)0.3087 (18)0.219 (5)0.774 (6)
H1310.20280.79640.16630.263*0.774 (6)
C14A0.284 (2)0.9425 (7)0.195 (3)0.382 (11)0.774 (6)
H1420.37150.93480.08700.574*0.774 (6)
H1410.30970.98540.33200.574*0.774 (6)
H1430.19760.97390.09320.574*0.774 (6)
C15A0.0997 (13)0.8609 (12)0.471 (3)0.343 (8)0.774 (6)
H1530.01870.89470.36230.515*0.774 (6)
H1510.13020.90550.60230.515*0.774 (6)
H1520.06230.79810.55060.515*0.774 (6)
C11B0.3342 (5)0.6684 (2)0.5442 (8)0.1283 (14)0.226 (6)
H1130.44110.68720.57260.154*0.226 (6)
H1140.29400.64290.70820.154*0.226 (6)
C12B0.2364 (14)0.7629 (5)0.434 (3)0.203 (4)0.226 (6)
H1230.22840.76040.24790.243*0.226 (6)
H1240.13220.75750.49910.243*0.226 (6)
C13B0.2968 (16)0.8678 (6)0.495 (2)0.219 (5)0.226 (6)
H1320.20840.91730.49300.263*0.226 (6)
C14B0.408 (3)0.904 (2)0.287 (4)0.382 (11)0.226 (6)
H1440.44150.97230.31960.574*0.226 (6)
H1450.35660.90610.12060.574*0.226 (6)
H1460.49740.85770.29040.574*0.226 (6)
C15B0.378 (3)0.8645 (19)0.761 (3)0.343 (8)0.226 (6)
H1540.39680.93360.80660.515*0.226 (6)
H1550.47550.82640.75720.515*0.226 (6)
H1560.31370.83140.88740.515*0.226 (6)
C210.2183 (4)0.3335 (3)0.1002 (8)0.1250 (14)
H2110.27820.34060.25550.150*
H2120.10910.33910.15190.150*
C220.2530 (7)0.2286 (4)0.0324 (12)0.171 (2)
H2230.22730.17650.08270.205*
H2220.19250.22050.18450.205*
H2210.36150.22190.08030.205*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0883 (14)0.142 (2)0.160 (2)0.0232 (14)0.0507 (15)0.0064 (17)
O20.0841 (14)0.1289 (19)0.153 (2)0.0235 (13)0.0434 (14)0.0172 (16)
N10.0761 (14)0.110 (2)0.121 (2)0.0094 (14)0.0330 (14)0.0047 (17)
N20.0749 (15)0.114 (2)0.134 (2)0.0090 (14)0.0292 (16)0.0123 (18)
C10.0783 (18)0.100 (2)0.124 (3)0.0042 (16)0.0224 (18)0.017 (2)
C20.0698 (17)0.112 (2)0.118 (3)0.0006 (17)0.0233 (18)0.007 (2)
C11A0.104 (3)0.111 (3)0.171 (4)0.009 (2)0.025 (3)0.006 (3)
C12A0.182 (7)0.128 (5)0.304 (10)0.031 (5)0.103 (8)0.009 (5)
C13A0.230 (9)0.173 (7)0.241 (11)0.039 (6)0.060 (8)0.074 (7)
C14A0.63 (3)0.120 (7)0.385 (19)0.002 (10)0.07 (2)0.054 (8)
C15A0.177 (9)0.357 (17)0.51 (2)0.045 (10)0.075 (12)0.105 (15)
C11B0.104 (3)0.111 (3)0.171 (4)0.009 (2)0.025 (3)0.006 (3)
C12B0.182 (7)0.128 (5)0.304 (10)0.031 (5)0.103 (8)0.009 (5)
C13B0.230 (9)0.173 (7)0.241 (11)0.039 (6)0.060 (8)0.074 (7)
C14B0.63 (3)0.120 (7)0.385 (19)0.002 (10)0.07 (2)0.054 (8)
C15B0.177 (9)0.357 (17)0.51 (2)0.045 (10)0.075 (12)0.105 (15)
C210.101 (2)0.131 (3)0.144 (4)0.004 (2)0.031 (2)0.008 (3)
C220.178 (5)0.141 (4)0.193 (5)0.007 (3)0.006 (4)0.014 (4)
Geometric parameters (Å, º) top
O1—C11.210 (4)C15A—H1530.9600
O2—C21.233 (4)C15A—H1510.9600
N1—C11.354 (4)C15A—H1520.9600
N1—C21.381 (5)C12B—C13B1.525 (12)
N1—H110.8600C12B—H1230.9700
N2—C21.319 (4)C12B—H1240.9700
N2—C211.436 (5)C13B—C15B1.53 (2)
N2—H210.8600C13B—C14B1.53 (3)
C1—C11A1.496 (5)C13B—H1320.9800
C11A—C12A1.523 (6)C14B—H1440.9600
C11A—H1110.9700C14B—H1450.9600
C11A—H1120.9700C14B—H1460.9600
C11A—C12B1.534 (10)C15B—H1540.9600
C12A—C13A1.522 (9)C15B—H1550.9600
C12A—H1210.9700C15B—H1560.9600
C12A—H1220.9700C21—C221.502 (6)
C13A—C15A1.522 (16)C21—H2110.9700
C13A—C14A1.530 (14)C21—H2120.9700
C13A—H1310.9800C22—H2230.9600
C14A—H1420.9600C22—H2220.9600
C14A—H1410.9600C22—H2210.9600
C14A—H1430.9600
C1—N1—C2128.7 (3)H153—C15A—H151109.5
C1—N1—H11115.7C13A—C15A—H152109.5
C2—N1—H11115.7H153—C15A—H152109.5
C2—N2—C21122.2 (3)H151—C15A—H152109.5
C2—N2—H21118.9C13B—C12B—H123108.3
C21—N2—H21118.9C13B—C12B—H124108.3
O1—C1—N1123.8 (3)H123—C12B—H124107.4
O1—C1—C11A122.4 (3)C12B—C13B—C15B112.0 (7)
N1—C1—C11A113.8 (3)C12B—C13B—C14B109.5 (7)
O2—C2—N2123.4 (4)C15B—C13B—C14B109.9 (7)
O2—C2—N1118.3 (3)C12B—C13B—H132108.4
N2—C2—N1118.3 (3)C15B—C13B—H132108.4
C1—C11A—C12A118.2 (4)C14B—C13B—H132108.4
C1—C11A—H111107.8C13B—C14B—H144109.5
C12A—C11A—H111107.8C13B—C14B—H145109.5
C1—C11A—H112107.8H144—C14B—H145109.5
C12A—C11A—H112107.8C13B—C14B—H146109.5
H111—C11A—H112107.1H144—C14B—H146109.5
C13A—C12A—C11A112.3 (5)H145—C14B—H146109.5
C13A—C12A—H121109.1C13B—C15B—H154109.5
C11A—C12A—H121109.1C13B—C15B—H155109.5
C13A—C12A—H122109.1H154—C15B—H155109.5
C11A—C12A—H122109.1C13B—C15B—H156109.5
H121—C12A—H122107.9H154—C15B—H156109.5
C12A—C13A—C15A117.0 (8)H155—C15B—H156109.5
C12A—C13A—C14A112.3 (9)N2—C21—C22112.8 (4)
C15A—C13A—C14A103.3 (11)N2—C21—H211109.0
C12A—C13A—H131108.0C22—C21—H211109.0
C15A—C13A—H131108.0N2—C21—H212109.0
C14A—C13A—H131108.0C22—C21—H212109.0
C13A—C14A—H142109.5H211—C21—H212107.8
C13A—C14A—H141109.5C21—C22—H223109.5
H142—C14A—H141109.5C21—C22—H222109.5
C13A—C14A—H143109.5H223—C22—H222109.5
H142—C14A—H143109.5C21—C22—H221109.5
H141—C14A—H143109.5H223—C22—H221109.5
C13A—C15A—H153109.5H222—C22—H221109.5
C13A—C15A—H151109.5
C2—N1—C1—O10.6 (6)C11A—C12A—C13A—C15A64.5 (11)
C2—N1—C1—C11A177.8 (3)C11A—C12A—C13A—C14A176.3 (9)
C21—N2—C2—O21.7 (5)C2—N2—C21—C2284.1 (5)
C21—N2—C2—N1177.6 (3)C2—N1—C1—C11B177.8 (3)
C1—N1—C2—O2177.8 (3)O1—C1—C11B—C12B100.4 (7)
C1—N1—C2—N21.6 (5)N1—C1—C11B—C12B81.1 (7)
O1—C1—C11A—C12A49.9 (5)C1—C11B—C12B—C13B145.1 (10)
N1—C1—C11A—C12A131.7 (4)C11B—C12B—C13B—C15B33.4 (17)
C1—C11A—C12A—C13A78.5 (7)C11B—C12B—C13B—C14B88.8 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.413.100 (3)138
N1—H11···O2ii0.862.002.855 (4)178
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(ethyl374K) 1-ethyl-3-(4-methylpentanoyl)urea top
Crystal data top
C9H18N2O2F(000) = 204
Mr = 186.25Dx = 1.044 Mg m3
Triclinic, P1Melting point: 375 K
a = 8.6337 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.1782 (16) ÅCell parameters from 1921 reflections
c = 5.2242 (18) Åθ = 1.6–27.4°
α = 85.948 (12)°µ = 0.07 mm1
β = 91.71 (2)°T = 374 K
γ = 88.030 (13)°Plate, colourless
V = 592.2 (2) Å31.00 × 0.60 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
826 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
Detector resolution: 10 pixels mm-1h = 1111
Oscillation method scansk = 1616
8267 measured reflectionsl = 66
1962 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.152Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.379H-atom parameters constrained
S = 1.85 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
1962 reflections(Δ/σ)max = 0.001
131 parametersΔρmax = 0.22 e Å3
17 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. The crystal was being high temperature phase.

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*/UeqOcc. (<1)
O10.4309 (4)0.5705 (3)0.2056 (8)0.1487 (15)
O20.0265 (4)0.4115 (2)0.2684 (8)0.1411 (15)
N10.1966 (4)0.5311 (3)0.3691 (9)0.1209 (14)
H110.13190.54830.48160.145*
N20.2533 (4)0.4162 (3)0.0625 (9)0.1289 (16)
H210.34120.44420.04460.155*
C10.3248 (5)0.5871 (3)0.3521 (10)0.1222 (18)
C20.1557 (5)0.4510 (4)0.2330 (11)0.1156 (17)
C11A0.3332 (6)0.6684 (3)0.5374 (11)0.148 (2)0.765 (6)
H1110.40930.64580.67150.178*0.765 (6)
H1120.23350.67340.61740.178*0.765 (6)
C12A0.3736 (9)0.7748 (5)0.435 (2)0.227 (5)0.765 (6)
H1220.45410.76920.31070.272*0.765 (6)
H1210.41540.81080.57580.272*0.765 (6)
C13A0.2368 (10)0.8371 (7)0.309 (2)0.248 (7)0.765 (6)
H1310.20040.79950.16500.298*0.765 (6)
C14A0.277 (2)0.9430 (8)0.194 (3)0.366 (14)0.765 (6)
H1420.36450.93690.08650.549*0.765 (6)
H1410.30210.98550.33040.549*0.765 (6)
H1430.18980.97280.09440.549*0.765 (6)
C15A0.0940 (18)0.8608 (14)0.463 (5)0.396 (14)0.765 (6)
H1530.01510.89440.35070.594*0.765 (6)
H1510.12150.90430.59540.594*0.765 (6)
H1520.05560.79850.53900.594*0.765 (6)
C11B0.3332 (6)0.6684 (3)0.5374 (11)0.148 (2)0.235 (6)
H1130.43890.69040.55260.178*0.235 (6)
H1140.30280.64150.70540.178*0.235 (6)
C12B0.2253 (14)0.7593 (6)0.444 (3)0.227 (5)0.235 (6)
H1230.21340.76070.25880.272*0.235 (6)
H1240.12400.74900.51490.272*0.235 (6)
C13B0.2811 (16)0.8627 (6)0.517 (2)0.248 (7)0.235 (6)
H1320.19280.91170.50450.298*0.235 (6)
C14B0.403 (3)0.900 (2)0.328 (4)0.366 (14)0.235 (6)
H1440.43300.96650.36600.549*0.235 (6)
H1450.36040.90140.15620.549*0.235 (6)
H1460.49230.85370.34470.549*0.235 (6)
C15B0.350 (4)0.856 (2)0.791 (3)0.396 (14)0.235 (6)
H1540.36910.92350.84090.594*0.235 (6)
H1550.44520.81640.79930.594*0.235 (6)
H1560.27770.82470.90590.594*0.235 (6)
C210.2164 (6)0.3329 (4)0.0932 (10)0.143 (2)
H2110.27180.33960.25200.172*
H2120.10620.33590.13640.172*
C220.2604 (9)0.2311 (4)0.0485 (16)0.204 (4)
H2230.23660.17720.05900.245*
H2220.20310.22350.20290.245*
H2210.36950.22810.09140.245*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.102 (2)0.168 (3)0.182 (3)0.029 (2)0.051 (2)0.024 (3)
O20.094 (2)0.140 (3)0.196 (4)0.0257 (18)0.052 (2)0.027 (2)
N10.083 (2)0.124 (3)0.160 (4)0.021 (2)0.039 (3)0.018 (3)
N20.087 (2)0.132 (3)0.173 (4)0.013 (2)0.039 (3)0.026 (3)
C10.084 (3)0.116 (3)0.165 (5)0.003 (3)0.027 (3)0.007 (3)
C20.064 (2)0.138 (4)0.142 (5)0.003 (3)0.015 (3)0.010 (3)
C11A0.115 (4)0.119 (4)0.213 (6)0.017 (3)0.030 (4)0.018 (4)
C12A0.187 (9)0.172 (7)0.325 (14)0.015 (7)0.108 (11)0.005 (8)
C13A0.204 (11)0.269 (12)0.248 (14)0.030 (10)0.074 (11)0.118 (12)
C14A0.62 (4)0.131 (9)0.34 (2)0.042 (13)0.03 (2)0.072 (10)
C15A0.181 (13)0.35 (2)0.68 (4)0.033 (13)0.10 (2)0.17 (2)
C11B0.115 (4)0.119 (4)0.213 (6)0.017 (3)0.030 (4)0.018 (4)
C12B0.187 (9)0.172 (7)0.325 (14)0.015 (7)0.108 (11)0.005 (8)
C13B0.204 (11)0.269 (12)0.248 (14)0.030 (10)0.074 (11)0.118 (12)
C14B0.62 (4)0.131 (9)0.34 (2)0.042 (13)0.03 (2)0.072 (10)
C15B0.181 (13)0.35 (2)0.68 (4)0.033 (13)0.10 (2)0.17 (2)
C210.103 (4)0.149 (4)0.178 (6)0.000 (3)0.037 (4)0.007 (4)
C220.192 (7)0.147 (5)0.278 (10)0.009 (5)0.043 (8)0.039 (6)
Geometric parameters (Å, º) top
O1—C11.234 (6)C15A—H1530.9600
O2—C21.261 (6)C15A—H1510.9600
N1—C11.353 (6)C15A—H1520.9600
N1—C21.364 (7)C12B—C13B1.530 (13)
N1—H110.8600C12B—H1230.9700
N2—C21.338 (6)C12B—H1240.9700
N2—C211.450 (7)C13B—C15B1.53 (2)
N2—H210.8600C13B—C14B1.53 (3)
C1—C11A1.496 (7)C13B—H1320.9800
C11A—C12A1.521 (9)C14B—H1440.9600
C11A—H1110.9700C14B—H1450.9600
C11A—H1120.9700C14B—H1460.9600
C11A—C12B1.53 (11)C15B—H1540.9600
C12A—C13A1.521 (12)C15B—H1550.9600
C12A—H1220.9700C15B—H1560.9600
C12A—H1210.9700C21—C221.517 (8)
C13A—C15A1.53 (2)C21—H2110.9700
C13A—C14A1.534 (16)C21—H2120.9700
C13A—H1310.9800C22—H2230.9600
C14A—H1420.9600C22—H2220.9600
C14A—H1410.9600C22—H2210.9600
C14A—H1430.9600
C1—N1—C2129.1 (4)H153—C15A—H151109.5
C1—N1—H11115.5C13A—C15A—H152109.5
C2—N1—H11115.5H153—C15A—H152109.5
C2—N2—C21122.5 (4)H151—C15A—H152109.5
C2—N2—H21118.8C13B—C12B—H123108.6
C21—N2—H21118.8C13B—C12B—H124108.6
O1—C1—N1123.6 (4)H123—C12B—H124107.6
O1—C1—C11A121.8 (4)C12B—C13B—C15B111.2 (7)
N1—C1—C11A114.5 (4)C12B—C13B—C14B109.3 (7)
O2—C2—N2121.1 (6)C15B—C13B—C14B109.9 (7)
O2—C2—N1119.6 (4)C12B—C13B—H132108.8
N2—C2—N1119.3 (4)C15B—C13B—H132108.8
C1—C11A—C12A118.1 (6)C14B—C13B—H132108.8
C1—C11A—H111107.8C13B—C14B—H144109.5
C12A—C11A—H111107.8C13B—C14B—H145109.5
C1—C11A—H112107.8H144—C14B—H145109.5
C12A—C11A—H112107.8C13B—C14B—H146109.5
H111—C11A—H112107.1H144—C14B—H146109.5
C11A—C12A—C13A113.9 (6)H145—C14B—H146109.5
C11A—C12A—H122108.8C13B—C15B—H154109.5
C13A—C12A—H122108.8C13B—C15B—H155109.5
C11A—C12A—H121108.8H154—C15B—H155109.5
C13A—C12A—H121108.8C13B—C15B—H156109.5
H122—C12A—H121107.7H154—C15B—H156109.5
C12A—C13A—C15A120.4 (12)H155—C15B—H156109.5
C12A—C13A—C14A114.5 (10)N2—C21—C22110.9 (5)
C15A—C13A—C14A102.2 (13)N2—C21—H211109.5
C12A—C13A—H131106.3C22—C21—H211109.5
C15A—C13A—H131106.3N2—C21—H212109.5
C14A—C13A—H131106.3C22—C21—H212109.5
C13A—C14A—H142109.5H211—C21—H212108.0
C13A—C14A—H141109.5C21—C22—H223109.5
H142—C14A—H141109.5C21—C22—H222109.5
C13A—C14A—H143109.5H223—C22—H222109.5
H142—C14A—H143109.5C21—C22—H221109.5
H141—C14A—H143109.5H223—C22—H221109.5
C13A—C15A—H153109.5H222—C22—H221109.5
C13A—C15A—H151109.5
C2—N1—C1—O12.0 (9)C11A—C12A—C13A—C15A60.1 (16)
C2—N1—C1—C11A178.7 (5)C11A—C12A—C13A—C14A177.4 (11)
C21—N2—C2—O21.0 (7)C2—N2—C21—C2286.2 (6)
C21—N2—C2—N1178.6 (5)C2—N1—C1—C11B178.7 (5)
C1—N1—C2—O2176.5 (5)O1—C1—C11B—C12B106.2 (9)
C1—N1—C2—N23.1 (8)N1—C1—C11B—C12B77.1 (8)
O1—C1—C11A—C12A51.0 (7)C1—C11B—C12B—C13B148.3 (10)
N1—C1—C11A—C12A132.3 (6)C11B—C12B—C13B—C15B40.8 (18)
C1—C11A—C12A—C13A81.4 (10)C11B—C12B—C13B—C14B80.6 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.862.403.107 (5)139
N1—H11···O2ii0.862.002.862 (5)178
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(propyl98K) 1-(4-methylpentanoyl)-3-propylurea top
Crystal data top
C10H20N2O2F(000) = 220
Mr = 200.28Dx = 1.123 Mg m3
Triclinic, P1Melting point: 381 K
a = 9.5437 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.205 (4) ÅCell parameters from 3224 reflections
c = 4.8457 (13) Åθ = 2.5–27.5°
α = 92.029 (14)°µ = 0.08 mm1
β = 98.767 (9)°T = 98 K
γ = 78.875 (17)°Plate, colourless
V = 592.2 (3) Å30.50 × 0.30 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1775 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
Detector resolution: 10 pixels mm-1h = 1112
Oscillation method scansk = 1617
6949 measured reflectionsl = 66
2162 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: difference Fourier map
wR(F2) = 0.168All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0588P)2 + 0.7784P]
where P = (Fo2 + 2Fc2)/3
2162 reflections(Δ/σ)max < 0.001
207 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.25 e Å3
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
O10.11921 (18)0.55649 (14)0.0569 (4)0.0314 (4)
O20.40312 (18)0.41157 (13)0.6112 (3)0.0297 (4)
N10.3321 (2)0.52101 (15)0.2434 (4)0.0245 (4)
H110.422 (4)0.542 (2)0.292 (6)0.042 (8)*
N20.1782 (2)0.41817 (16)0.3633 (4)0.0271 (5)
H210.115 (4)0.445 (2)0.224 (7)0.041 (8)*
C10.2423 (2)0.57155 (18)0.0234 (5)0.0248 (5)
C20.3061 (2)0.44630 (17)0.4180 (5)0.0246 (5)
C110.3039 (3)0.65149 (18)0.1090 (5)0.0252 (5)
H1110.414 (3)0.626 (2)0.111 (6)0.042 (8)*
H1120.255 (3)0.662 (2)0.304 (6)0.029 (7)*
C120.2811 (3)0.75336 (19)0.0561 (5)0.0296 (5)
H1210.336 (3)0.744 (2)0.247 (6)0.034 (7)*
H1220.174 (4)0.773 (2)0.079 (7)0.049 (9)*
C130.3259 (3)0.84217 (19)0.0817 (6)0.0318 (6)
H1310.268 (3)0.851 (2)0.267 (6)0.037 (8)*
C140.2853 (4)0.9422 (2)0.0804 (8)0.0484 (8)
H1410.177 (4)0.960 (3)0.084 (7)0.059 (10)*
H1420.308 (4)1.002 (3)0.020 (8)0.064 (11)*
H1430.336 (4)0.935 (3)0.277 (9)0.070 (11)*
C150.4853 (3)0.8202 (3)0.1093 (8)0.0471 (8)
H1510.512 (5)0.880 (3)0.185 (8)0.079 (13)*
H1520.539 (4)0.809 (3)0.077 (7)0.051 (10)*
H1530.510 (4)0.755 (3)0.239 (7)0.061 (10)*
C210.1370 (3)0.34246 (19)0.5315 (5)0.0270 (5)
H2110.204 (3)0.333 (2)0.707 (6)0.032 (7)*
H2120.037 (3)0.369 (2)0.581 (6)0.032 (7)*
C220.1387 (3)0.2395 (2)0.3795 (6)0.0338 (6)
H2210.241 (4)0.210 (2)0.341 (7)0.045 (8)*
H2220.080 (4)0.252 (3)0.189 (7)0.057 (10)*
C230.0812 (4)0.1644 (2)0.5410 (7)0.0403 (7)
H2310.136 (4)0.153 (3)0.729 (7)0.049 (9)*
H2320.084 (4)0.096 (3)0.456 (7)0.063 (11)*
H2330.019 (4)0.195 (3)0.572 (7)0.053 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0236 (9)0.0398 (10)0.0299 (9)0.0107 (7)0.0062 (7)0.0047 (7)
O20.0252 (9)0.0352 (9)0.0268 (9)0.0087 (7)0.0067 (7)0.0045 (7)
N10.0221 (10)0.0286 (10)0.0233 (10)0.0094 (8)0.0014 (8)0.0010 (7)
N20.0236 (11)0.0332 (11)0.0244 (10)0.0108 (8)0.0041 (8)0.0038 (8)
C10.0228 (12)0.0285 (12)0.0220 (11)0.0052 (9)0.0005 (9)0.0030 (9)
C20.0241 (12)0.0287 (11)0.0207 (11)0.0082 (9)0.0010 (9)0.0036 (8)
C110.0259 (12)0.0287 (11)0.0209 (11)0.0068 (9)0.0002 (9)0.0006 (8)
C120.0344 (14)0.0294 (12)0.0263 (12)0.0087 (10)0.0061 (10)0.0019 (9)
C130.0337 (14)0.0298 (13)0.0320 (13)0.0092 (10)0.0008 (11)0.0021 (10)
C140.062 (2)0.0305 (15)0.0533 (19)0.0095 (14)0.0100 (17)0.0029 (13)
C150.0377 (17)0.0450 (17)0.064 (2)0.0187 (13)0.0093 (15)0.0040 (15)
C210.0249 (12)0.0323 (12)0.0243 (11)0.0099 (9)0.0009 (10)0.0029 (9)
C220.0367 (15)0.0318 (13)0.0360 (14)0.0095 (11)0.0122 (12)0.0016 (10)
C230.0489 (18)0.0333 (14)0.0438 (17)0.0143 (12)0.0148 (14)0.0007 (12)
Geometric parameters (Å, º) top
O1—C11.231 (3)C13—H1310.98 (3)
O2—C21.244 (3)C14—H1411.01 (4)
N1—C11.367 (3)C14—H1421.02 (4)
N1—C21.403 (3)C14—H1431.00 (4)
N1—H110.95 (3)C15—H1510.97 (4)
N2—C21.329 (3)C15—H1520.97 (4)
N2—C211.458 (3)C15—H1531.06 (4)
N2—H210.87 (3)C21—C221.522 (4)
C1—C111.508 (3)C21—H2110.98 (3)
C11—C121.537 (3)C21—H2121.01 (3)
C11—H1111.04 (3)C22—C231.515 (4)
C11—H1120.99 (3)C22—H2211.03 (3)
C12—C131.530 (3)C22—H2221.00 (4)
C12—H1210.99 (3)C23—H2310.98 (3)
C12—H1221.03 (3)C23—H2320.98 (4)
C13—C151.518 (4)C23—H2331.00 (4)
C13—C141.528 (4)
C1—N1—C2128.9 (2)C13—C14—H141111 (2)
C1—N1—H11116.0 (18)C13—C14—H142110 (2)
C2—N1—H11115.0 (18)H141—C14—H142105 (3)
C2—N2—C21122.3 (2)C13—C14—H143110 (2)
C2—N2—H21120 (2)H141—C14—H143109 (3)
C21—N2—H21117 (2)H142—C14—H143113 (3)
O1—C1—N1123.6 (2)C13—C15—H151110 (3)
O1—C1—C11122.0 (2)C13—C15—H152107 (2)
N1—C1—C11114.4 (2)H151—C15—H152108 (3)
O2—C2—N2125.0 (2)C13—C15—H153111 (2)
O2—C2—N1118.1 (2)H151—C15—H153110 (3)
N2—C2—N1116.9 (2)H152—C15—H153111 (3)
C1—C11—C12110.1 (2)N2—C21—C22111.7 (2)
C1—C11—H111110.4 (17)N2—C21—H211108.6 (16)
C12—C11—H111108.8 (17)C22—C21—H211110.1 (16)
C1—C11—H112108.5 (15)N2—C21—H212110.0 (16)
C12—C11—H112110.3 (16)C22—C21—H212109.3 (16)
H111—C11—H112109 (2)H211—C21—H212107 (2)
C13—C12—C11113.5 (2)C23—C22—C21111.7 (2)
C13—C12—H121108.4 (16)C23—C22—H221111.5 (17)
C11—C12—H121110.0 (16)C21—C22—H221109.3 (17)
C13—C12—H122109.8 (18)C23—C22—H222111 (2)
C11—C12—H122108.3 (18)C21—C22—H222109 (2)
H121—C12—H122107 (2)H221—C22—H222104 (3)
C15—C13—C14111.3 (3)C22—C23—H231111.7 (19)
C15—C13—C12112.3 (2)C22—C23—H232115 (2)
C14—C13—C12109.7 (2)H231—C23—H232106 (3)
C15—C13—H131109.7 (17)C22—C23—H233109.7 (19)
C14—C13—H131107.0 (17)H231—C23—H233104 (3)
C12—C13—H131106.6 (17)H232—C23—H233110 (3)
C2—N1—C1—O10.7 (4)N1—C1—C11—C1283.1 (3)
C2—N1—C1—C11177.0 (2)C1—C11—C12—C13173.8 (2)
C21—N2—C2—O20.8 (4)C11—C12—C13—C1561.3 (3)
C21—N2—C2—N1179.1 (2)C11—C12—C13—C14174.3 (2)
C1—N1—C2—O2178.6 (2)C2—N2—C21—C22106.1 (3)
C1—N1—C2—N21.3 (4)N2—C21—C22—C23174.1 (2)
O1—C1—C11—C1294.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O2i0.95 (3)1.88 (3)2.820 (3)178 (3)
N2—H21···O1ii0.87 (3)2.26 (3)2.959 (3)137 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z.
(propyl298K) 1-(4-methylpentanoyl)-3-propylurea top
Crystal data top
C10H20N2O2F(000) = 220
Mr = 200.28Dx = 1.017 Mg m3
Triclinic, P1Melting point: 381 K
a = 9.547 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.688 (6) ÅCell parameters from 3480 reflections
c = 5.1166 (16) Åθ = 1.5–27.2°
α = 90.902 (14)°µ = 0.07 mm1
β = 97.109 (8)°T = 298 K
γ = 80.47 (2)°Plate, colourless
V = 654.3 (4) Å30.50 × 0.30 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
1178 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
Detector resolution: 10 pixels mm-1h = 1212
Oscillation method scansk = 1717
10255 measured reflectionsl = 66
2485 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.117Hydrogen site location: difference Fourier map
wR(F2) = 0.377H-atom parameters constrained
S = 1.97 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
2485 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.34 e Å3
6 restraintsΔρmin = 0.32 e Å3
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
O10.1236 (3)0.5584 (3)0.0332 (6)0.1050 (12)
O20.3975 (3)0.4154 (2)0.5961 (6)0.0975 (11)
N10.3307 (3)0.5232 (2)0.2512 (6)0.0836 (11)
H110.41370.54010.28630.100*
N20.1742 (3)0.4212 (3)0.3621 (7)0.0911 (12)
H210.11540.44840.23250.109*
C10.2437 (4)0.5731 (3)0.0441 (8)0.0811 (11)
C20.3029 (4)0.4485 (3)0.4130 (8)0.0808 (11)
C110.3108 (4)0.6517 (3)0.0726 (8)0.0900 (13)
H1110.27510.65970.25820.108*
H1120.41370.63100.05750.108*
C120.2772 (5)0.7513 (3)0.0675 (10)0.1093 (16)
H1210.17470.76610.07370.131*
H1220.32300.74390.24780.131*
C130.3234 (6)0.8397 (3)0.0551 (13)0.134 (2)
H1310.28100.84470.23990.160*
C140.2702 (10)0.9370 (4)0.0806 (19)0.217 (5)
H1410.16810.94560.07580.261*
H1430.29560.99140.00940.261*
H1420.31370.93510.26040.261*
C150.4856 (6)0.8229 (6)0.049 (2)0.209 (4)
H1510.51380.87830.12930.251*
H1520.51560.76360.14400.251*
H1530.52970.81610.13040.251*
C210.1313 (4)0.3472 (3)0.5193 (8)0.0930 (14)
H2110.03170.36710.54490.112*
H2120.18780.34330.69100.112*
C220.1503 (6)0.2446 (3)0.3913 (11)0.1219 (18)
H2210.09910.24920.21480.146*
H2220.25100.22240.37690.146*
C230.0952 (7)0.1689 (4)0.5501 (15)0.150 (2)
H2320.10680.10610.46240.180*
H2310.00430.19080.56530.180*
H2330.14850.16220.72250.180*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0711 (15)0.133 (3)0.109 (2)0.0320 (15)0.0182 (15)0.031 (2)
O20.0768 (16)0.109 (2)0.104 (2)0.0281 (15)0.0173 (16)0.0273 (17)
N10.0662 (16)0.100 (3)0.085 (2)0.0257 (16)0.0085 (15)0.0091 (18)
N20.0703 (17)0.112 (3)0.093 (2)0.0310 (17)0.0100 (16)0.0215 (19)
C10.0654 (17)0.098 (3)0.080 (2)0.0186 (18)0.0014 (17)0.002 (2)
C20.0667 (19)0.091 (3)0.085 (2)0.0214 (18)0.0011 (19)0.006 (2)
C110.087 (2)0.099 (3)0.086 (2)0.019 (2)0.011 (2)0.009 (2)
C120.111 (3)0.100 (4)0.124 (4)0.023 (3)0.036 (3)0.007 (3)
C130.147 (5)0.102 (4)0.160 (5)0.031 (3)0.037 (4)0.018 (4)
C140.271 (12)0.101 (5)0.298 (11)0.032 (6)0.105 (10)0.005 (6)
C150.153 (6)0.157 (6)0.347 (13)0.075 (5)0.080 (8)0.006 (8)
C210.080 (2)0.105 (3)0.096 (3)0.027 (2)0.003 (2)0.017 (3)
C220.122 (4)0.106 (4)0.144 (4)0.024 (3)0.035 (4)0.006 (3)
C230.165 (6)0.110 (4)0.183 (6)0.029 (4)0.045 (5)0.016 (4)
Geometric parameters (Å, º) top
O1—C11.213 (5)C13—H1310.9800
O2—C21.252 (4)C14—H1410.9600
N1—C11.377 (5)C14—H1430.9600
N1—C21.404 (6)C14—H1420.9600
N1—H110.8600C15—H1510.9600
N2—C21.337 (5)C15—H1520.9600
N2—C211.444 (6)C15—H1530.9600
N2—H210.8600C21—C221.533 (6)
C1—C111.506 (6)C21—H2110.9700
C11—C121.534 (6)C21—H2120.9700
C11—H1110.9700C22—C231.524 (9)
C11—H1120.9700C22—H2210.9700
C12—C131.524 (7)C22—H2220.9700
C12—H1210.9700C23—H2320.9600
C12—H1220.9700C23—H2310.9600
C13—C151.524 (8)C23—H2330.9600
C13—C141.532 (9)
C1—N1—C2129.2 (3)C13—C14—H141109.5
C1—N1—H11115.4C13—C14—H143109.5
C2—N1—H11115.4H141—C14—H143109.5
C2—N2—C21121.7 (3)C13—C14—H142109.5
C2—N2—H21119.2H141—C14—H142109.5
C21—N2—H21119.2H143—C14—H142109.5
O1—C1—N1124.3 (4)C13—C15—H151109.5
O1—C1—C11122.7 (4)C13—C15—H152109.5
N1—C1—C11112.9 (3)H151—C15—H152109.5
O2—C2—N2125.5 (4)C13—C15—H153109.5
O2—C2—N1118.1 (3)H151—C15—H153109.5
N2—C2—N1116.4 (3)H152—C15—H153109.5
C1—C11—C12111.3 (3)N2—C21—C22112.4 (3)
C1—C11—H111109.4N2—C21—H211109.1
C12—C11—H111109.4C22—C21—H211109.1
C1—C11—H112109.4N2—C21—H212109.1
C12—C11—H112109.4C22—C21—H212109.1
H111—C11—H112108.0H211—C21—H212107.9
C13—C12—C11116.1 (4)C23—C22—C21111.7 (4)
C13—C12—H121108.3C23—C22—H221109.3
C11—C12—H121108.3C21—C22—H221109.3
C13—C12—H122108.3C23—C22—H222109.3
C11—C12—H122108.3C21—C22—H222109.3
H121—C12—H122107.4H221—C22—H222107.9
C12—C13—C15109.9 (4)C22—C23—H232109.5
C12—C13—C14111.9 (4)C22—C23—H231109.5
C15—C13—C14111.1 (6)H232—C23—H231109.5
C12—C13—H131107.9C22—C23—H233109.5
C15—C13—H131107.9H232—C23—H233109.5
C14—C13—H131107.9H231—C23—H233109.5
C2—N1—C1—O10.4 (7)N1—C1—C11—C1288.8 (5)
C2—N1—C1—C11177.4 (4)C1—C11—C12—C13172.6 (4)
C21—N2—C2—O20.5 (7)C11—C12—C13—C1562.5 (8)
C21—N2—C2—N1178.3 (4)C11—C12—C13—C14173.6 (6)
C1—N1—C2—O2178.0 (4)C2—N2—C21—C2298.4 (5)
C1—N1—C2—N20.1 (6)N2—C21—C22—C23176.1 (5)
O1—C1—C11—C1289.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O2i0.862.022.873 (4)174
N2—H21···O1ii0.862.403.092 (4)138
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z.
(propyl348K) 1-(4-methylpentanoyl)-3-propylurea top
Crystal data top
C10H20N2O2F(000) = 220
Mr = 200.28Dx = 1.053 Mg m3
Triclinic, P1Melting point: 381 K
a = 9.405 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.3600 (19) ÅCell parameters from 1956 reflections
c = 5.1686 (8) Åθ = 2.2–25.7°
α = 93.609 (13)°µ = 0.07 mm1
β = 98.144 (12)°T = 348 K
γ = 79.387 (10)°Plate, colourless
V = 631.46 (19) Å30.50 × 0.30 × 0.10 mm
Z = 2
Data collection top
RIGAKU RAXIS-RAPID
diffractometer
861 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.078
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
Detector resolution: 10 pixels mm-1h = 1012
Oscillation method scansk = 1316
10152 measured reflectionsl = 65
1576 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.140Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.391H-atom parameters constrained
S = 2.05 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
1576 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.23 e Å3
6 restraintsΔρmin = 0.18 e Å3
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
O10.1244 (5)0.5604 (4)0.0247 (11)0.123 (2)
O20.3953 (5)0.4151 (4)0.5898 (11)0.118 (2)
N10.3332 (5)0.5239 (4)0.2559 (12)0.0920 (18)
H110.41810.54040.29460.110*
N20.1729 (6)0.4231 (4)0.3557 (12)0.105 (2)
H210.11350.44950.22560.126*
C10.2465 (7)0.5732 (5)0.0567 (14)0.089 (2)
C20.3033 (7)0.4487 (5)0.4096 (16)0.095 (2)
C110.3133 (8)0.6498 (5)0.0617 (16)0.110 (2)
H1110.27530.65520.24580.132*
H1120.41830.62790.04720.132*
C120.2778 (9)0.7532 (5)0.0799 (19)0.138 (3)
H1210.33010.74990.25580.166*
H1220.17410.76820.09370.166*
C130.3184 (12)0.8392 (6)0.060 (2)0.170 (4)
H1310.27650.83990.24470.204*
C140.267 (2)0.9396 (8)0.084 (4)0.308 (11)
H1410.16200.95150.07290.370*
H1420.29640.99430.00630.370*
H1430.30850.93610.26480.370*
C150.4845 (12)0.8228 (9)0.028 (3)0.266 (9)
H1510.51490.87740.10570.319*
H1520.52130.75920.11270.319*
H1530.52200.82150.15480.319*
C210.1277 (8)0.3497 (5)0.5162 (16)0.118 (3)
H2110.02410.36860.52810.141*
H2120.18000.35130.69170.141*
C220.1598 (12)0.2423 (5)0.393 (2)0.162 (4)
H2210.26400.22100.39210.194*
H2220.11210.24100.21420.194*
C230.1023 (15)0.1705 (7)0.556 (2)0.192 (5)
H2310.15300.17020.73060.231*
H2320.11810.10280.47820.231*
H2330.00030.19350.56040.231*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.079 (3)0.154 (5)0.132 (4)0.029 (3)0.020 (3)0.023 (3)
O20.090 (3)0.129 (4)0.131 (4)0.038 (3)0.031 (3)0.030 (3)
N10.068 (3)0.103 (4)0.106 (4)0.030 (3)0.005 (3)0.007 (4)
N20.079 (3)0.118 (4)0.122 (5)0.039 (3)0.009 (3)0.022 (4)
C10.068 (4)0.106 (5)0.088 (5)0.014 (3)0.007 (4)0.007 (4)
C20.067 (4)0.101 (5)0.114 (6)0.024 (4)0.007 (4)0.006 (4)
C110.102 (5)0.121 (6)0.110 (6)0.028 (4)0.013 (5)0.005 (5)
C120.121 (6)0.128 (7)0.180 (9)0.039 (5)0.049 (6)0.001 (7)
C130.173 (10)0.123 (7)0.227 (13)0.043 (7)0.048 (9)0.006 (8)
C140.39 (2)0.117 (9)0.46 (3)0.067 (11)0.16 (2)0.018 (13)
C150.194 (14)0.175 (11)0.46 (3)0.078 (10)0.069 (16)0.046 (15)
C210.081 (4)0.150 (7)0.122 (6)0.037 (4)0.004 (4)0.001 (6)
C220.195 (10)0.124 (7)0.181 (11)0.063 (7)0.036 (9)0.015 (8)
C230.255 (14)0.126 (7)0.216 (13)0.063 (8)0.062 (11)0.011 (8)
Geometric parameters (Å, º) top
O1—C11.206 (8)C13—H1310.9800
O2—C21.224 (9)C14—H1410.9600
N1—C11.345 (8)C14—H1420.9600
N1—C21.410 (10)C14—H1430.9600
N1—H110.8600C15—H1510.9600
N2—C21.320 (9)C15—H1520.9600
N2—C211.479 (11)C15—H1530.9600
N2—H210.8600C21—C221.528 (10)
C1—C111.496 (11)C21—H2110.9700
C11—C121.526 (10)C21—H2120.9700
C11—H1110.9700C22—C231.529 (17)
C11—H1120.9700C22—H2210.9700
C12—C131.528 (14)C22—H2220.9700
C12—H1210.9700C23—H2310.9600
C12—H1220.9700C23—H2320.9600
C13—C151.524 (15)C23—H2330.9600
C13—C141.526 (16)
C1—N1—C2128.5 (5)C13—C14—H141109.5
C1—N1—H11115.7C13—C14—H142109.5
C2—N1—H11115.7H141—C14—H142109.5
C2—N2—C21120.9 (7)C13—C14—H143109.5
C2—N2—H21119.6H141—C14—H143109.5
C21—N2—H21119.6H142—C14—H143109.5
O1—C1—N1125.1 (7)C13—C15—H151109.5
O1—C1—C11120.6 (7)C13—C15—H152109.5
N1—C1—C11114.3 (6)H151—C15—H152109.5
O2—C2—N2124.4 (8)C13—C15—H153109.5
O2—C2—N1118.8 (6)H151—C15—H153109.5
N2—C2—N1116.8 (7)H152—C15—H153109.5
C1—C11—C12109.5 (6)N2—C21—C22110.0 (6)
C1—C11—H111109.8N2—C21—H211109.7
C12—C11—H111109.8C22—C21—H211109.7
C1—C11—H112109.8N2—C21—H212109.7
C12—C11—H112109.8C22—C21—H212109.7
H111—C11—H112108.2H211—C21—H212108.2
C11—C12—C13112.5 (7)C21—C22—C23108.0 (7)
C11—C12—H121109.1C21—C22—H221110.1
C13—C12—H121109.1C23—C22—H221110.1
C11—C12—H122109.1C21—C22—H222110.1
C13—C12—H122109.1C23—C22—H222110.1
H121—C12—H122107.8H221—C22—H222108.4
C15—C13—C14107.1 (11)C22—C23—H231109.5
C15—C13—C12106.7 (7)C22—C23—H232109.5
C14—C13—C12108.1 (7)H231—C23—H232109.5
C15—C13—H131111.6C22—C23—H233109.5
C14—C13—H131111.6H231—C23—H233109.5
C12—C13—H131111.6H232—C23—H233109.5
C2—N1—C1—O10.1 (11)N1—C1—C11—C1289.8 (8)
C2—N1—C1—C11179.4 (6)C1—C11—C12—C13169.7 (8)
C21—N2—C2—O20.2 (11)C11—C12—C13—C1569.9 (11)
C21—N2—C2—N1176.2 (6)C11—C12—C13—C14175.2 (11)
C1—N1—C2—O2177.4 (6)C2—N2—C21—C2293.9 (8)
C1—N1—C2—N20.8 (10)N2—C21—C22—C23176.4 (8)
O1—C1—C11—C1289.5 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O2i0.861.962.815 (7)175
N2—H21···O1ii0.862.353.043 (8)138
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z.
 

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